# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SX17021R
_database_code_depnum_ccdc_archive 'CCDC 1905889'
loop_
_audit_author_name
_audit_author_address
'Akira Tsubouchi'
;Tokyo University of Agriculture and Technology
Japan
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-04-24 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H18 N2 O'
_chemical_formula_moiety         'C16 H18 N2 O'
_chemical_formula_weight         254.33
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   17.1343(2)
_cell_length_b                   10.09453(12)
_cell_length_c                   15.4280(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.6644(12)
_cell_angle_gamma                90.0000
_cell_volume                     2665.58(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16415
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      68.21
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.131
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.052
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088.00
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_T_max  0.968

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            25304
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         2.582
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4873
_reflns_number_gt                4374
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0977
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4873
_refine_ls_number_parameters     347
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0416P)²+1.2236P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C C 0.0180 0.0090 'International Tables Vol.C Table 6.1.1.4.'
'International Tables Vol.C Table 4.2.6.8.'
H H 0.0000 0.0000 'International Tables Vol.C Table 6.1.1.4.'
'International Tables Vol.C Table 4.2.6.8.'
N N 0.0310 0.0180 'International Tables Vol.C Table 6.1.1.4.'
'International Tables Vol.C Table 4.2.6.8.'
O O 0.0490 0.0320 'International Tables Vol.C Table 6.1.1.4.'
'International Tables Vol.C Table 4.2.6.8.'

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45819(6) 0.80343(10) 0.51770(7) 0.0273(2) Uani 1 1 d . . . . .
O2 O 1.01311(6) 0.31107(10) 0.52793(7) 0.0315(2) Uani 1 1 d . . . . .
N3 N 0.90707(6) -0.06197(11) 0.45898(8) 0.0230(2) Uani 1 1 d . . . . .
H3 H 0.9468 -0.1151 0.4711 0.028 Uiso 1 1 calc R U . . .
N4 N 0.60125(6) 0.45966(11) 0.47468(7) 0.0222(2) Uani 1 1 d . . . . .
H4 H 0.5672 0.3961 0.4826 0.027 Uiso 1 1 calc R U . . .
N5 N 0.58322(7) 0.85525(11) 0.55425(7) 0.0238(3) Uani 1 1 d . . . . .
N6 N 0.88356(7) 0.32639(12) 0.54427(8) 0.0259(3) Uani 1 1 d . . . . .
C7 C 0.61976(7) 0.56031(13) 0.53312(9) 0.0214(3) Uani 1 1 d . . . . .
C8 C 0.86668(8) -0.05403(13) 0.38059(9) 0.0226(3) Uani 1 1 d . . . . .
C9 C 0.67635(8) 0.64045(14) 0.49891(9) 0.0234(3) Uani 1 1 d . . . . .
C10 C 0.64420(8) 0.47438(14) 0.40258(9) 0.0233(3) Uani 1 1 d . . . . .
C11 C 0.87567(8) 0.02683(13) 0.51633(9) 0.0225(3) Uani 1 1 d . . . . .
C12 C 0.58493(8) 0.56249(14) 0.61809(9) 0.0234(3) Uani 1 1 d . . . . .
C13 C 0.80643(7) 0.04069(13) 0.38832(9) 0.0226(3) Uani 1 1 d . . . . .
C14 C 0.69174(8) 0.58808(14) 0.41524(9) 0.0236(3) Uani 1 1 d . . . . .
C15 C 0.90639(8) 0.03407(14) 0.60666(9) 0.0245(3) Uani 1 1 d . . . . .
C16 C 0.52320(8) 0.84135(13) 0.49566(9) 0.0232(3) Uani 1 1 d . . . . .
C17 C 0.94717(8) 0.33574(14) 0.49611(10) 0.0261(3) Uani 1 1 d . . . . .
C18 C 0.81311(8) 0.09079(14) 0.47510(9) 0.0233(3) Uani 1 1 d . . . . .
C19 C 0.56911(8) 0.67072(15) 0.66390(9) 0.0257(3) Uani 1 1 d . . . . .
H19 H 0.5532 0.6519 0.7208 0.031 Uiso 1 1 calc R U . . .
C20 C 0.87872(8) -0.12078(14) 0.30319(10) 0.0261(3) Uani 1 1 d . . . . .
H20 H 0.9204 -0.1820 0.2987 0.031 Uiso 1 1 calc R U . . .
C21 C 0.75464(8) 0.06313(14) 0.31652(10) 0.0263(3) Uani 1 1 d . . . . .
H21 H 0.7127 0.1241 0.3203 0.032 Uiso 1 1 calc R U . . .
C22 C 0.66383(8) 0.88286(14) 0.53236(10) 0.0270(3) Uani 1 1 d . . . . .
H22A H 0.6858 0.9535 0.5708 0.032 Uiso 1 1 calc R U . . .
H22B H 0.6647 0.9146 0.4717 0.032 Uiso 1 1 calc R U . . .
C23 C 0.76411(8) 0.19606(14) 0.51443(10) 0.0268(3) Uani 1 1 d . . . . .
H23A H 0.7562 0.1739 0.5759 0.032 Uiso 1 1 calc R U . . .
H23B H 0.7122 0.1988 0.4835 0.032 Uiso 1 1 calc R U . . .
C24 C 0.80278(8) 0.33254(14) 0.50933(10) 0.0276(3) Uani 1 1 d . . . . .
H24A H 0.8020 0.3624 0.4482 0.033 Uiso 1 1 calc R U . . .
H24B H 0.7731 0.3975 0.5428 0.033 Uiso 1 1 calc R U . . .
C25 C 0.76561(8) -0.00458(15) 0.24063(10) 0.0282(3) Uani 1 1 d . . . . .
H25 H 0.7305 0.0097 0.1921 0.034 Uiso 1 1 calc R U . . .
C26 C 0.64682(8) 0.39530(15) 0.32895(10) 0.0276(3) Uani 1 1 d . . . . .
H26 H 0.6140 0.3199 0.3213 0.033 Uiso 1 1 calc R U . . .
C27 C 0.57140(9) 0.81651(14) 0.64368(9) 0.0271(3) Uani 1 1 d . . . . .
H27A H 0.5216 0.8561 0.6610 0.033 Uiso 1 1 calc R U . . .
H27B H 0.6137 0.8568 0.6808 0.033 Uiso 1 1 calc R U . . .
C28 C 0.90983(8) 0.14389(15) 0.65513(9) 0.0275(3) Uani 1 1 d . . . . .
H28 H 0.9245 0.1278 0.7143 0.033 Uiso 1 1 calc R U . . .
C29 C 0.82770(8) -0.09443(15) 0.23335(10) 0.0282(3) Uani 1 1 d . . . . .
H29 H 0.8347 -0.1377 0.1796 0.034 Uiso 1 1 calc R U . . .
C30 C 0.71375(8) 0.75788(14) 0.54295(10) 0.0277(3) Uani 1 1 d . . . . .
H30A H 0.7653 0.7740 0.5185 0.033 Uiso 1 1 calc R U . . .
H30B H 0.7226 0.7383 0.6055 0.033 Uiso 1 1 calc R U . . .
C31 C 0.74333(8) 0.62255(15) 0.35061(10) 0.0296(3) Uani 1 1 d . . . . .
H31 H 0.7754 0.6991 0.3569 0.036 Uiso 1 1 calc R U . . .
C32 C 0.53656(9) 0.87525(14) 0.40228(9) 0.0285(3) Uani 1 1 d . . . . .
H32A H 0.5590 0.9643 0.3991 0.043 Uiso 1 1 calc R U . . .
H32B H 0.4867 0.8725 0.3686 0.043 Uiso 1 1 calc R U . . .
H32C H 0.5727 0.8109 0.3785 0.043 Uiso 1 1 calc R U . . .
C33 C 0.56564(9) 0.42787(15) 0.65487(10) 0.0297(3) Uani 1 1 d . . . . .
H33A H 0.5187 0.3927 0.6243 0.045 Uiso 1 1 calc R U . . .
H33B H 0.5563 0.4366 0.7168 0.045 Uiso 1 1 calc R U . . .
H33C H 0.6095 0.3673 0.6473 0.045 Uiso 1 1 calc R U . . .
C34 C 0.93659(9) -0.09492(15) 0.64519(10) 0.0312(3) Uani 1 1 d . . . . .
H34A H 0.8986 -0.1655 0.6322 0.047 Uiso 1 1 calc R U . . .
H34B H 0.9444 -0.0853 0.7082 0.047 Uiso 1 1 calc R U . . .
H34C H 0.9864 -0.1175 0.6201 0.047 Uiso 1 1 calc R U . . .
C35 C 0.74661(9) 0.54350(16) 0.27817(10) 0.0339(4) Uani 1 1 d . . . . .
H35 H 0.7818 0.5656 0.2346 0.041 Uiso 1 1 calc R U . . .
C36 C 0.69913(9) 0.43089(16) 0.26737(10) 0.0326(3) Uani 1 1 d . . . . .
H36 H 0.7030 0.3781 0.2168 0.039 Uiso 1 1 calc R U . . .
C37 C 0.89519(9) 0.28775(15) 0.63492(10) 0.0304(3) Uani 1 1 d . . . . .
H37A H 0.8484 0.3155 0.6656 0.036 Uiso 1 1 calc R U . . .
H37B H 0.9400 0.3391 0.6601 0.036 Uiso 1 1 calc R U . . .
C38 C 0.93599(9) 0.37939(16) 0.40306(10) 0.0326(3) Uani 1 1 d . . . . .
H38A H 0.9083 0.4643 0.4006 0.049 Uiso 1 1 calc R U . . .
H38B H 0.9053 0.3128 0.3702 0.049 Uiso 1 1 calc R U . . .
H38C H 0.9871 0.3895 0.3778 0.049 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 5.0rc6 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 5.0rc6'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.2403(17) . ?
O2 C17 1.2361(18) . ?
N3 C8 1.3675(18) . ?
N3 C11 1.3857(18) . ?
N3 H3 0.8800 . ?
N4 C10 1.3702(17) . ?
N4 C7 1.3853(18) . ?
N4 H4 0.8800 . ?
N5 C16 1.3446(19) . ?
N5 C27 1.4574(18) . ?
N5 C22 1.4638(17) . ?
N6 C17 1.3506(19) . ?
N6 C37 1.4567(19) . ?
N6 C24 1.4632(18) . ?
C7 C9 1.3860(19) . ?
C7 C12 1.4656(19) . ?
C8 C20 1.395(2) . ?
C8 C13 1.4163(19) . ?
C9 C14 1.431(2) . ?
C9 C30 1.496(2) . ?
C10 C26 1.391(2) . ?
C10 C14 1.416(2) . ?
C11 C18 1.381(2) . ?
C11 C15 1.468(2) . ?
C12 C19 1.336(2) . ?
C12 C33 1.5151(19) . ?
C13 C21 1.405(2) . ?
C13 C18 1.431(2) . ?
C14 C31 1.4066(19) . ?
C15 C28 1.337(2) . ?
C15 C34 1.513(2) . ?
C16 C32 1.5085(19) . ?
C17 C38 1.505(2) . ?
C18 C23 1.4999(19) . ?
C19 C27 1.505(2) . ?
C19 H19 0.9500 . ?
C20 C29 1.381(2) . ?
C20 H20 0.9500 . ?
C21 C25 1.376(2) . ?
C21 H21 0.9500 . ?
C22 C30 1.529(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.532(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C29 1.407(2) . ?
C25 H25 0.9500 . ?
C26 C36 1.384(2) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C37 1.504(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C35 1.377(2) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.403(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N3 C11 109.35(11) . . ?
C8 N3 H3 125.3 . . ?
C11 N3 H3 125.3 . . ?
C10 N4 C7 109.48(11) . . ?
C10 N4 H4 125.3 . . ?
C7 N4 H4 125.3 . . ?
C16 N5 C27 118.22(11) . . ?
C16 N5 C22 124.41(12) . . ?
C27 N5 C22 116.33(12) . . ?
C17 N6 C37 117.97(12) . . ?
C17 N6 C24 124.61(12) . . ?
C37 N6 C24 116.74(12) . . ?
N4 C7 C9 108.87(12) . . ?
N4 C7 C12 120.18(12) . . ?
C9 C7 C12 130.76(13) . . ?
N3 C8 C20 129.79(13) . . ?
N3 C8 C13 107.82(12) . . ?
C20 C8 C13 122.39(13) . . ?
C7 C9 C14 106.82(12) . . ?
C7 C9 C30 125.61(13) . . ?
C14 C9 C30 127.57(12) . . ?
N4 C10 C26 129.77(13) . . ?
N4 C10 C14 107.66(12) . . ?
C26 C10 C14 122.54(13) . . ?
C18 C11 N3 108.93(12) . . ?
C18 C11 C15 130.55(13) . . ?
N3 C11 C15 120.37(12) . . ?
C19 C12 C7 125.92(13) . . ?
C19 C12 C33 118.84(12) . . ?
C7 C12 C33 115.24(12) . . ?
C21 C13 C8 118.59(13) . . ?
C21 C13 C18 134.49(13) . . ?
C8 C13 C18 106.89(12) . . ?
C31 C14 C10 118.64(13) . . ?
C31 C14 C9 134.14(14) . . ?
C10 C14 C9 107.16(12) . . ?
C28 C15 C11 125.21(13) . . ?
C28 C15 C34 119.25(13) . . ?
C11 C15 C34 115.54(13) . . ?
O1 C16 N5 121.09(13) . . ?
O1 C16 C32 120.66(13) . . ?
N5 C16 C32 118.23(12) . . ?
O2 C17 N6 120.89(14) . . ?
O2 C17 C38 120.74(13) . . ?
N6 C17 C38 118.36(13) . . ?
C11 C18 C13 107.00(12) . . ?
C11 C18 C23 125.59(13) . . ?
C13 C18 C23 127.37(13) . . ?
C12 C19 C27 133.01(13) . . ?
C12 C19 H19 113.5 . . ?
C27 C19 H19 113.5 . . ?
C29 C20 C8 117.48(13) . . ?
C29 C20 H20 121.3 . . ?
C8 C20 H20 121.3 . . ?
C25 C21 C13 118.98(13) . . ?
C25 C21 H21 120.5 . . ?
C13 C21 H21 120.5 . . ?
N5 C22 C30 110.33(11) . . ?
N5 C22 H22A 109.6 . . ?
C30 C22 H22A 109.6 . . ?
N5 C22 H22B 109.6 . . ?
C30 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C18 C23 C24 111.39(11) . . ?
C18 C23 H23A 109.3 . . ?
C24 C23 H23A 109.3 . . ?
C18 C23 H23B 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
N6 C24 C23 110.29(11) . . ?
N6 C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
N6 C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C21 C25 C29 121.46(14) . . ?
C21 C25 H25 119.3 . . ?
C29 C25 H25 119.3 . . ?
C36 C26 C10 117.28(14) . . ?
C36 C26 H26 121.4 . . ?
C10 C26 H26 121.4 . . ?
N5 C27 C19 117.69(12) . . ?
N5 C27 H27A 107.9 . . ?
C19 C27 H27A 107.9 . . ?
N5 C27 H27B 107.9 . . ?
C19 C27 H27B 107.9 . . ?
H27A C27 H27B 107.2 . . ?
C15 C28 C37 133.01(14) . . ?
C15 C28 H28 113.5 . . ?
C37 C28 H28 113.5 . . ?
C20 C29 C25 121.03(14) . . ?
C20 C29 H29 119.5 . . ?
C25 C29 H29 119.5 . . ?
C9 C30 C22 112.32(12) . . ?
C9 C30 H30A 109.1 . . ?
C22 C30 H30A 109.1 . . ?
C9 C30 H30B 109.1 . . ?
C22 C30 H30B 109.1 . . ?
H30A C30 H30B 107.9 . . ?
C35 C31 C14 118.87(14) . . ?
C35 C31 H31 120.6 . . ?
C14 C31 H31 120.6 . . ?
C16 C32 H32A 109.5 . . ?
C16 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C16 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C12 C33 H33A 109.5 . . ?
C12 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C12 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C15 C34 H34A 109.5 . . ?
C15 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C15 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C31 C35 C36 121.38(14) . . ?
C31 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
C26 C36 C35 121.28(15) . . ?
C26 C36 H36 119.4 . . ?
C35 C36 H36 119.4 . . ?
N6 C37 C28 118.14(12) . . ?
N6 C37 H37A 107.8 . . ?
C28 C37 H37A 107.8 . . ?
N6 C37 H37B 107.8 . . ?
C28 C37 H37B 107.8 . . ?
H37A C37 H37B 107.1 . . ?
C17 C38 H38A 109.5 . . ?
C17 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C17 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N4 C7 C9 -0.82(15) . . . . ?
C10 N4 C7 C12 -176.41(12) . . . . ?
C11 N3 C8 C20 177.72(13) . . . . ?
C11 N3 C8 C13 -1.27(15) . . . . ?
N4 C7 C9 C14 1.30(15) . . . . ?
C12 C7 C9 C14 176.26(13) . . . . ?
N4 C7 C9 C30 -178.15(12) . . . . ?
C12 C7 C9 C30 -3.2(2) . . . . ?
C7 N4 C10 C26 177.84(14) . . . . ?
C7 N4 C10 C14 -0.01(15) . . . . ?
C8 N3 C11 C18 1.36(15) . . . . ?
C8 N3 C11 C15 177.36(12) . . . . ?
N4 C7 C12 C19 -149.51(14) . . . . ?
C9 C7 C12 C19 36.0(2) . . . . ?
N4 C7 C12 C33 30.18(18) . . . . ?
C9 C7 C12 C33 -144.31(15) . . . . ?
N3 C8 C13 C21 -177.69(11) . . . . ?
C20 C8 C13 C21 3.2(2) . . . . ?
N3 C8 C13 C18 0.71(15) . . . . ?
C20 C8 C13 C18 -178.37(12) . . . . ?
N4 C10 C14 C31 178.31(12) . . . . ?
C26 C10 C14 C31 0.3(2) . . . . ?
N4 C10 C14 C9 0.80(15) . . . . ?
C26 C10 C14 C9 -177.24(13) . . . . ?
C7 C9 C14 C31 -178.24(15) . . . . ?
C30 C9 C14 C31 1.2(3) . . . . ?
C7 C9 C14 C10 -1.29(15) . . . . ?
C30 C9 C14 C10 178.15(13) . . . . ?
C18 C11 C15 C28 -37.6(2) . . . . ?
N3 C11 C15 C28 147.36(14) . . . . ?
C18 C11 C15 C34 142.96(15) . . . . ?
N3 C11 C15 C34 -32.06(17) . . . . ?
C27 N5 C16 O1 3.86(19) . . . . ?
C22 N5 C16 O1 171.81(12) . . . . ?
C27 N5 C16 C32 -177.12(12) . . . . ?
C22 N5 C16 C32 -9.17(19) . . . . ?
C37 N6 C17 O2 0.6(2) . . . . ?
C24 N6 C17 O2 -169.64(13) . . . . ?
C37 N6 C17 C38 -178.28(13) . . . . ?
C24 N6 C17 C38 11.5(2) . . . . ?
N3 C11 C18 C13 -0.88(15) . . . . ?
C15 C11 C18 C13 -176.34(13) . . . . ?
N3 C11 C18 C23 -178.93(12) . . . . ?
C15 C11 C18 C23 5.6(2) . . . . ?
C21 C13 C18 C11 178.14(15) . . . . ?
C8 C13 C18 C11 0.11(15) . . . . ?
C21 C13 C18 C23 -3.9(2) . . . . ?
C8 C13 C18 C23 178.12(13) . . . . ?
C7 C12 C19 C27 8.0(3) . . . . ?
C33 C12 C19 C27 -171.68(15) . . . . ?
N3 C8 C20 C29 179.20(13) . . . . ?
C13 C8 C20 C29 -1.9(2) . . . . ?
C8 C13 C21 C25 -1.90(19) . . . . ?
C18 C13 C21 C25 -179.76(14) . . . . ?
C16 N5 C22 C30 -104.67(15) . . . . ?
C27 N5 C22 C30 63.48(16) . . . . ?
C11 C18 C23 C24 82.67(17) . . . . ?
C13 C18 C23 C24 -94.98(16) . . . . ?
C17 N6 C24 C23 109.36(15) . . . . ?
C37 N6 C24 C23 -61.01(16) . . . . ?
C18 C23 C24 N6 -51.37(16) . . . . ?
C13 C21 C25 C29 -0.6(2) . . . . ?
N4 C10 C26 C36 -176.82(14) . . . . ?
C14 C10 C26 C36 0.8(2) . . . . ?
C16 N5 C27 C19 74.46(17) . . . . ?
C22 N5 C27 C19 -94.47(15) . . . . ?
C12 C19 C27 N5 9.3(2) . . . . ?
C11 C15 C28 C37 -8.4(3) . . . . ?
C34 C15 C28 C37 170.99(15) . . . . ?
C8 C20 C29 C25 -0.6(2) . . . . ?
C21 C25 C29 C20 1.9(2) . . . . ?
C7 C9 C30 C22 -82.62(17) . . . . ?
C14 C9 C30 C22 98.04(16) . . . . ?
N5 C22 C30 C9 49.19(16) . . . . ?
C10 C14 C31 C35 -1.0(2) . . . . ?
C9 C14 C31 C35 175.69(15) . . . . ?
C14 C31 C35 C36 0.7(2) . . . . ?
C10 C26 C36 C35 -1.1(2) . . . . ?
C31 C35 C36 C26 0.3(2) . . . . ?
C17 N6 C37 C28 -77.32(18) . . . . ?
C24 N6 C37 C28 93.71(16) . . . . ?
C15 C28 C37 N6 -8.8(2) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3 O2 . . 3_756 2.8651(15) 0.880 2.0936(10) 145.90(8) no
N4 H4 O1 . . 3_666 2.8487(15) 0.880 2.0605(10) 148.60(8) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_User-defined
_database_code_depnum_ccdc_archive 'CCDC 1905916'
loop_
_audit_author_name
_audit_author_address
'Akira Tsubouchi'
;Tokyo University of Agriculture and Technology
Japan
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-04-24 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H18 N2'
_chemical_formula_moiety         'C16 H18 N2'
_chemical_formula_weight         238.33
_chemical_melting_point          ?
_chemical_absolute_configuration ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.1973(16)
_cell_length_b                   11.006(3)
_cell_length_c                   16.413(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1300.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8490
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.60
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512.00
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_T_max  0.986

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.849
_diffrn_reflns_number            12176
_diffrn_reflns_av_R_equivalents  0.1697
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2978
_reflns_number_gt                1611
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1419
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2978
_refine_ls_number_parameters     164
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0481P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.170
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.018(4)
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1249 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00000

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0973(5) 0.8756(3) 0.1328(2) 0.0426(9) Uani 1.0 4 d . . .
N2 N -0.3452(5) 0.7485(4) 0.2045(2) 0.0508(10) Uani 1.0 4 d . . .
C3 C -0.1445(7) 1.0657(4) -0.0135(3) 0.0454(12) Uani 1.0 4 d . . .
C4 C -0.1028(6) 0.9828(4) 0.0462(3) 0.0364(10) Uani 1.0 4 d . . .
C5 C 0.0800(6) 0.9645(4) 0.0698(3) 0.0380(10) Uani 1.0 4 d . . .
C6 C 0.2239(7) 1.0289(4) 0.0351(3) 0.0483(12) Uani 1.0 4 d . . .
C7 C 0.1819(7) 1.1124(4) -0.0253(3) 0.0533(13) Uani 1.0 4 d . . .
C8 C 0.0002(8) 1.1315(4) -0.0494(3) 0.0527(13) Uani 1.0 4 d . . .
C9 C -0.2194(6) 0.9024(4) 0.0984(3) 0.0341(10) Uani 1.0 4 d . . .
C10 C -0.3345(6) 0.8017(4) 0.0561(3) 0.0458(12) Uani 1.0 4 d . . .
C11 C -0.4101(7) 0.7161(4) 0.1225(3) 0.0576(14) Uani 1.0 4 d . . .
C12 C -0.4187(7) 0.8716(4) 0.2205(3) 0.0553(13) Uani 1.0 4 d . . .
C13 C -0.3404(6) 0.9646(4) 0.1612(3) 0.0378(10) Uani 1.0 4 d . . .
C14 C -0.3690(6) 1.0808(4) 0.1671(3) 0.0535(13) Uani 1.0 4 d . . .
C15 C -0.0704(6) 0.8408(4) 0.1479(3) 0.0363(11) Uani 1.0 4 d . . .
C16 C -0.1373(6) 0.7489(4) 0.2093(3) 0.0458(11) Uani 1.0 4 d . . .
C17 C -0.0738(8) 0.7823(5) 0.2950(3) 0.0647(15) Uani 1.0 4 d . . .
C18 C -0.0633(8) 0.6227(4) 0.1893(3) 0.0648(15) Uani 1.0 4 d . . .
H3 H -0.2694 1.0782 -0.0301 0.0544 Uiso 1.0 4 calc R . .
H6 H 0.3486 1.0162 0.0521 0.0580 Uiso 1.0 4 calc R . .
H7 H 0.2791 1.1572 -0.0504 0.0640 Uiso 1.0 4 calc R . .
H8 H -0.0266 1.1895 -0.0905 0.0632 Uiso 1.0 4 calc R . .
H10A H -0.4386 0.8383 0.0252 0.0550 Uiso 1.0 4 calc R . .
H10B H -0.2553 0.7558 0.0175 0.0550 Uiso 1.0 4 calc R . .
H11A H -0.5475 0.7184 0.1215 0.0692 Uiso 1.0 4 calc R . .
H11B H -0.3709 0.6319 0.1100 0.0692 Uiso 1.0 4 calc R . .
H12A H -0.3867 0.8958 0.2769 0.0663 Uiso 1.0 4 calc R . .
H12B H -0.5558 0.8702 0.2159 0.0663 Uiso 1.0 4 calc R . .
H14A H -0.3113 1.1350 0.1298 0.0641 Uiso 1.0 4 calc R . .
H14B H -0.4477 1.1117 0.2088 0.0641 Uiso 1.0 4 calc R . .
H17A H 0.0623 0.7822 0.2972 0.0776 Uiso 1.0 4 calc R . .
H17B H -0.1203 0.8633 0.3089 0.0776 Uiso 1.0 4 calc R . .
H17C H -0.1226 0.7228 0.3339 0.0776 Uiso 1.0 4 calc R . .
H18A H 0.0727 0.6231 0.1925 0.0778 Uiso 1.0 4 calc R . .
H18B H -0.1131 0.5639 0.2285 0.0778 Uiso 1.0 4 calc R . .
H18C H -0.1019 0.5999 0.1341 0.0778 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_structure_solution    'SHELXD (Schneider, et al., 2002)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N1 C5 1.430(5) yes . .
N1 C15 1.291(6) yes . .
N2 C11 1.469(6) yes . .
N2 C12 1.477(6) yes . .
N2 C16 1.498(6) yes . .
C3 C4 1.372(6) yes . .
C3 C8 1.398(7) yes . .
C4 C5 1.386(6) yes . .
C4 C9 1.490(6) yes . .
C5 C6 1.378(6) yes . .
C6 C7 1.385(7) yes . .
C7 C8 1.382(7) yes . .
C9 C10 1.549(6) yes . .
C9 C13 1.513(6) yes . .
C9 C15 1.505(6) yes . .
C10 C11 1.540(7) yes . .
C12 C13 1.521(6) yes . .
C13 C14 1.300(7) yes . .
C15 C16 1.507(6) yes . .
C16 C17 1.523(6) yes . .
C16 C18 1.523(6) yes . .
C3 H3 0.950 no . .
C6 H6 0.950 no . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C10 H10A 0.990 no . .
C10 H10B 0.990 no . .
C11 H11A 0.990 no . .
C11 H11B 0.990 no . .
C12 H12A 0.990 no . .
C12 H12B 0.990 no . .
C14 H14A 0.950 no . .
C14 H14B 0.950 no . .
C17 H17A 0.980 no . .
C17 H17B 0.980 no . .
C17 H17C 0.980 no . .
C18 H18A 0.980 no . .
C18 H18B 0.980 no . .
C18 H18C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C5 N1 C15 105.1(4) yes . . .
C11 N2 C12 105.8(4) yes . . .
C11 N2 C16 111.5(4) yes . . .
C12 N2 C16 110.2(4) yes . . .
C4 C3 C8 118.8(4) yes . . .
C3 C4 C5 120.2(4) yes . . .
C3 C4 C9 133.0(4) yes . . .
C5 C4 C9 106.8(4) yes . . .
N1 C5 C4 112.6(4) yes . . .
N1 C5 C6 125.8(4) yes . . .
C4 C5 C6 121.6(4) yes . . .
C5 C6 C7 118.2(5) yes . . .
C6 C7 C8 120.8(5) yes . . .
C3 C8 C7 120.4(4) yes . . .
C4 C9 C10 117.9(4) yes . . .
C4 C9 C13 116.6(4) yes . . .
C4 C9 C15 100.1(3) yes . . .
C10 C9 C13 108.7(4) yes . . .
C10 C9 C15 107.5(3) yes . . .
C13 C9 C15 104.3(4) yes . . .
C9 C10 C11 108.0(4) yes . . .
N2 C11 C10 112.8(4) yes . . .
N2 C12 C13 111.7(4) yes . . .
C9 C13 C12 110.2(4) yes . . .
C9 C13 C14 126.0(4) yes . . .
C12 C13 C14 123.8(4) yes . . .
N1 C15 C9 115.4(4) yes . . .
N1 C15 C16 128.7(4) yes . . .
C9 C15 C16 115.8(4) yes . . .
N2 C16 C15 106.6(4) yes . . .
N2 C16 C17 110.4(4) yes . . .
N2 C16 C18 109.6(4) yes . . .
C15 C16 C17 111.1(4) yes . . .
C15 C16 C18 110.9(4) yes . . .
C17 C16 C18 108.3(4) yes . . .
C4 C3 H3 120.582 no . . .
C8 C3 H3 120.585 no . . .
C5 C6 H6 120.905 no . . .
C7 C6 H6 120.912 no . . .
C6 C7 H7 119.601 no . . .
C8 C7 H7 119.605 no . . .
C3 C8 H8 119.810 no . . .
C7 C8 H8 119.814 no . . .
C9 C10 H10A 110.101 no . . .
C9 C10 H10B 110.100 no . . .
C11 C10 H10A 110.102 no . . .
C11 C10 H10B 110.096 no . . .
H10A C10 H10B 108.437 no . . .
N2 C11 H11A 109.019 no . . .
N2 C11 H11B 109.030 no . . .
C10 C11 H11A 109.026 no . . .
C10 C11 H11B 109.025 no . . .
H11A C11 H11B 107.803 no . . .
N2 C12 H12A 109.275 no . . .
N2 C12 H12B 109.273 no . . .
C13 C12 H12A 109.279 no . . .
C13 C12 H12B 109.279 no . . .
H12A C12 H12B 107.932 no . . .
C13 C14 H14A 119.999 no . . .
C13 C14 H14B 120.005 no . . .
H14A C14 H14B 119.996 no . . .
C16 C17 H17A 109.469 no . . .
C16 C17 H17B 109.469 no . . .
C16 C17 H17C 109.464 no . . .
H17A C17 H17B 109.475 no . . .
H17A C17 H17C 109.476 no . . .
H17B C17 H17C 109.474 no . . .
C16 C18 H18A 109.471 no . . .
C16 C18 H18B 109.470 no . . .
C16 C18 H18C 109.469 no . . .
H18A C18 H18B 109.480 no . . .
H18A C18 H18C 109.464 no . . .
H18B C18 H18C 109.474 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 N1 C15 C9 -0.9(4) no . . . .
C5 N1 C15 C16 -179.5(4) no . . . .
C15 N1 C5 C4 -0.3(4) no . . . .
C15 N1 C5 C6 178.7(4) no . . . .
C11 N2 C12 C13 -63.0(4) no . . . .
C12 N2 C11 C10 62.2(4) no . . . .
C11 N2 C16 C15 59.5(4) no . . . .
C11 N2 C16 C17 -179.8(3) no . . . .
C11 N2 C16 C18 -60.6(4) no . . . .
C16 N2 C11 C10 -57.6(5) no . . . .
C12 N2 C16 C15 -57.7(4) no . . . .
C12 N2 C16 C17 63.1(4) no . . . .
C12 N2 C16 C18 -177.8(3) no . . . .
C16 N2 C12 C13 57.7(4) no . . . .
C4 C3 C8 C7 0.4(6) no . . . .
C8 C3 C4 C5 -0.4(6) no . . . .
C8 C3 C4 C9 177.3(4) no . . . .
C3 C4 C5 N1 179.7(4) no . . . .
C3 C4 C5 C6 0.6(6) no . . . .
C3 C4 C9 C10 64.2(6) no . . . .
C3 C4 C9 C13 -67.9(6) no . . . .
C3 C4 C9 C15 -179.6(4) no . . . .
C5 C4 C9 C10 -117.8(4) no . . . .
C5 C4 C9 C13 110.0(4) no . . . .
C5 C4 C9 C15 -1.7(4) no . . . .
C9 C4 C5 N1 1.4(5) no . . . .
C9 C4 C5 C6 -177.7(3) no . . . .
N1 C5 C6 C7 -179.6(4) no . . . .
C4 C5 C6 C7 -0.7(6) no . . . .
C5 C6 C7 C8 0.6(7) no . . . .
C6 C7 C8 C3 -0.5(7) no . . . .
C4 C9 C10 C11 168.7(3) no . . . .
C4 C9 C13 C12 -168.3(3) no . . . .
C4 C9 C13 C14 8.9(6) no . . . .
C4 C9 C15 N1 1.6(4) no . . . .
C4 C9 C15 C16 -179.6(3) no . . . .
C10 C9 C13 C12 55.5(4) no . . . .
C10 C9 C13 C14 -127.3(4) no . . . .
C13 C9 C10 C11 -55.6(4) no . . . .
C10 C9 C15 N1 125.3(4) no . . . .
C10 C9 C15 C16 -55.9(4) no . . . .
C15 C9 C10 C11 56.7(4) no . . . .
C13 C9 C15 N1 -119.4(4) no . . . .
C13 C9 C15 C16 59.4(4) no . . . .
C15 C9 C13 C12 -58.9(4) no . . . .
C15 C9 C13 C14 118.2(4) no . . . .
C9 C10 C11 N2 -3.2(5) no . . . .
N2 C12 C13 C9 4.1(5) no . . . .
N2 C12 C13 C14 -173.1(4) no . . . .
N1 C15 C16 N2 176.9(4) no . . . .
N1 C15 C16 C17 56.6(6) no . . . .
N1 C15 C16 C18 -63.9(5) no . . . .
C9 C15 C16 N2 -1.7(5) no . . . .
C9 C15 C16 C17 -122.0(4) no . . . .
C9 C15 C16 C18 117.5(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 C10 3.451(6) no . .
N1 C13 3.332(6) no . .
N1 C17 3.107(6) no . .
N1 C18 3.153(6) no . .
N2 C9 2.592(6) no . .
C3 C6 2.798(7) no . .
C3 C10 3.408(6) no . .
C3 C13 3.384(6) no . .
C3 C14 3.381(7) no . .
C4 C7 2.759(6) no . .
C4 C14 2.962(6) no . .
C5 C8 2.744(6) no . .
C5 C10 3.487(6) no . .
C5 C13 3.378(6) no . .
C6 C15 3.493(6) no . .
C10 C12 2.871(6) no . .
C10 C14 3.581(7) no . .
C10 C16 2.946(6) no . .
C10 C18 3.532(7) no . .
C11 C13 2.852(7) no . .
C11 C15 2.834(7) no . .
C11 C18 2.913(7) no . .
C12 C15 2.796(7) no . .
C12 C17 2.936(7) no . .
C13 C16 2.897(6) no . .
C13 C17 3.539(7) no . .
C14 C15 3.420(6) no . .
N2 C14 3.475(6) no . 3_445
C14 N2 3.475(6) no . 3_455
N1 H6 2.7243 no . .
N1 H10B 3.4293 no . .
N1 H17A 2.8976 no . .
N1 H17B 3.2902 no . .
N1 H18A 2.9515 no . .
N1 H18C 3.3563 no . .
N2 H10A 3.1762 no . .
N2 H10B 3.1374 no . .
N2 H17A 3.3238 no . .
N2 H17B 2.6748 no . .
N2 H17C 2.6748 no . .
N2 H18A 3.3146 no . .
N2 H18B 2.6597 no . .
N2 H18C 2.6597 no . .
C3 H7 3.2671 no . .
C3 H10A 3.3392 no . .
C3 H10B 3.5391 no . .
C3 H14A 2.7489 no . .
C4 H6 3.2710 no . .
C4 H8 3.2432 no . .
C4 H10A 2.9138 no . .
C4 H10B 2.7685 no . .
C4 H14A 2.6348 no . .
C5 H3 3.2523 no . .
C5 H7 3.2310 no . .
C5 H10B 3.4400 no . .
C5 H14A 3.5247 no . .
C6 H8 3.2600 no . .
C7 H3 3.2709 no . .
C8 H6 3.2664 no . .
C9 H3 2.8854 no . .
C9 H11A 3.1344 no . .
C9 H11B 3.1765 no . .
C9 H12A 3.1678 no . .
C9 H12B 3.1158 no . .
C9 H14A 2.6934 no . .
C9 H14B 3.3593 no . .
C9 H17B 3.5540 no . .
C9 H18C 3.4845 no . .
C10 H3 3.3885 no . .
C10 H12B 3.1605 no . .
C10 H18C 3.0620 no . .
C11 H12A 3.2193 no . .
C11 H12B 2.5160 no . .
C11 H18B 3.2251 no . .
C11 H18C 2.5669 no . .
C12 H10A 3.2299 no . .
C12 H11A 2.5181 no . .
C12 H11B 3.2195 no . .
C12 H14A 3.3495 no . .
C12 H14B 2.6583 no . .
C12 H17B 2.5938 no . .
C12 H17C 3.2686 no . .
C13 H3 3.4191 no . .
C13 H10A 2.7230 no . .
C13 H10B 3.3488 no . .
C13 H11A 3.1600 no . .
C13 H17B 3.1031 no . .
C14 H3 3.3164 no . .
C14 H10A 3.5783 no . .
C14 H12A 2.7218 no . .
C14 H12B 2.7966 no . .
C15 H10A 3.3277 no . .
C15 H10B 2.6871 no . .
C15 H11B 3.2169 no . .
C15 H12A 3.1674 no . .
C15 H17A 2.7080 no . .
C15 H17B 2.6795 no . .
C15 H17C 3.3395 no . .
C15 H18A 2.7087 no . .
C15 H18B 3.3368 no . .
C15 H18C 2.6706 no . .
C16 H10B 3.2610 no . .
C16 H11A 3.3025 no . .
C16 H11B 2.6719 no . .
C16 H12A 2.6583 no . .
C16 H12B 3.2969 no . .
C17 H12A 2.5923 no . .
C17 H18A 2.6472 no . .
C17 H18B 2.6544 no . .
C17 H18C 3.3219 no . .
C18 H10B 3.4649 no . .
C18 H11B 2.5697 no . .
C18 H17A 2.6509 no . .
C18 H17B 3.3219 no . .
C18 H17C 2.6504 no . .
H3 H8 2.3537 no . .
H3 H10A 3.0465 no . .
H3 H14A 2.7156 no . .
H6 H7 2.3425 no . .
H7 H8 2.3236 no . .
H10A H11A 2.2032 no . .
H10A H11B 2.7083 no . .
H10A H12B 3.2606 no . .
H10B H11A 2.7400 no . .
H10B H11B 2.2040 no . .
H10B H18C 2.7975 no . .
H11A H12A 3.4140 no . .
H11A H12B 2.2792 no . .
H11A H18C 3.4684 no . .
H11B H12B 3.4166 no . .
H11B H18A 3.4684 no . .
H11B H18B 2.7896 no . .
H11B H18C 2.0066 no . .
H12A H14B 2.6624 no . .
H12A H17A 3.4807 no . .
H12A H17B 2.0203 no . .
H12A H17C 2.8484 no . .
H12B H14B 2.7717 no . .
H12B H17B 3.4880 no . .
H17A H18A 2.4534 no . .
H17A H18B 2.9379 no . .
H17A H18C 3.5463 no . .
H17B H18A 3.5453 no . .
H17B H18B 3.5506 no . .
H17C H18A 2.9266 no . .
H17C H18B 2.4606 no . .
H17C H18C 3.5494 no . .
N1 H10A 3.5126 no . 2_565
N1 H10B 3.0512 no . 2_565
N1 H11A 3.0922 no . 1_655
N1 H12B 2.8451 no . 1_655
N1 H18B 3.0802 no . 3_555
N2 H8 3.5541 no . 4_475
N2 H14B 2.5526 no . 3_445
C3 H7 3.2711 no . 2_475
C3 H11B 3.3344 no . 2_565
C3 H12A 3.4738 no . 4_474
C3 H17B 3.4602 no . 4_474
C4 H11A 3.5556 no . 2_565
C4 H11B 3.3101 no . 2_565
C5 H10B 3.0562 no . 2_565
C5 H11B 3.1560 no . 2_565
C5 H17C 3.2670 no . 3_555
C5 H18B 3.4954 no . 3_555
C6 H10A 3.2133 no . 1_655
C6 H10B 3.2536 no . 2_565
C6 H11B 3.0445 no . 2_565
C6 H17C 3.1164 no . 3_555
C6 H18C 3.3607 no . 2_565
C7 H3 3.5415 no . 2_575
C7 H8 3.5731 no . 2_575
C7 H11B 3.0515 no . 2_565
C7 H14A 3.2675 no . 2_575
C7 H17C 3.3945 no . 3_555
C7 H18C 3.3283 no . 2_565
C8 H7 3.2590 no . 2_475
C8 H11B 3.2021 no . 2_565
C8 H12A 2.9815 no . 4_474
C8 H14A 3.1927 no . 2_575
C8 H17B 3.5903 no . 4_474
C9 H6 3.4375 no . 1_455
C10 H6 3.2834 no . 1_455
C10 H10A 3.5033 no . 2_565
C10 H10B 3.3216 no . 2_465
C10 H11A 3.5796 no . 2_565
C11 H10B 3.3988 no . 2_465
C11 H14B 3.1684 no . 3_445
C12 H8 3.1972 no . 4_475
C12 H14B 3.2326 no . 3_445
C13 H6 2.9226 no . 1_455
C13 H18A 3.5392 no . 3_555
C14 H6 2.8637 no . 1_455
C14 H8 3.0419 no . 2_475
C14 H17A 3.1825 no . 3_555
C14 H18A 3.1744 no . 3_555
C15 H10A 3.5855 no . 2_565
C15 H18B 3.4484 no . 3_555
C17 H3 3.4457 no . 4_475
C17 H7 3.3746 no . 4_575
C17 H8 3.4498 no . 4_475
C17 H14A 3.4404 no . 3_545
C17 H18B 3.4008 no . 3_555
C18 H17B 3.1458 no . 3_545
H3 C7 3.5415 no . 2_475
H3 C17 3.4457 no . 4_474
H3 H6 3.1375 no . 1_455
H3 H7 3.3804 no . 1_455
H3 H7 3.2165 no . 2_475
H3 H12A 3.3728 no . 4_474
H3 H17B 2.8322 no . 4_474
H3 H17C 3.2222 no . 4_474
H3 H18C 3.5334 no . 2_465
H6 C9 3.4375 no . 1_655
H6 C10 3.2834 no . 1_655
H6 C13 2.9226 no . 1_655
H6 C14 2.8637 no . 1_655
H6 H3 3.1375 no . 1_655
H6 H8 3.4196 no . 2_575
H6 H10A 2.5251 no . 1_655
H6 H10B 3.2911 no . 2_565
H6 H11A 3.5499 no . 1_655
H6 H11B 3.4977 no . 2_565
H6 H12B 3.2070 no . 1_655
H6 H14A 3.0539 no . 1_655
H6 H14B 3.1411 no . 1_655
H6 H17C 3.3638 no . 3_555
H6 H18C 3.3324 no . 2_565
H7 C3 3.2711 no . 2_575
H7 C8 3.2590 no . 2_575
H7 C17 3.3746 no . 4_574
H7 H3 3.3804 no . 1_655
H7 H3 3.2165 no . 2_575
H7 H8 3.1860 no . 2_575
H7 H11B 3.4999 no . 2_565
H7 H14A 2.7119 no . 2_575
H7 H17A 2.8307 no . 4_574
H7 H17B 3.3784 no . 4_574
H7 H17C 3.3862 no . 4_574
H7 H18C 3.2611 no . 2_565
H8 N2 3.5541 no . 4_474
H8 C7 3.5731 no . 2_475
H8 C12 3.1972 no . 4_474
H8 C14 3.0419 no . 2_575
H8 C17 3.4498 no . 4_474
H8 H6 3.4196 no . 2_475
H8 H7 3.1860 no . 2_475
H8 H12A 2.4507 no . 4_474
H8 H12B 3.2979 no . 4_474
H8 H14A 2.5586 no . 2_575
H8 H14B 2.9789 no . 2_575
H8 H17B 3.0859 no . 4_474
H8 H17C 2.9741 no . 4_474
H10A N1 3.5126 no . 2_465
H10A C6 3.2133 no . 1_455
H10A C10 3.5033 no . 2_465
H10A C15 3.5855 no . 2_465
H10A H6 2.5251 no . 1_455
H10A H10B 2.6001 no . 2_465
H10A H18A 3.5992 no . 2_465
H10A H18C 2.9474 no . 2_465
H10B N1 3.0512 no . 2_465
H10B C5 3.0562 no . 2_465
H10B C6 3.2536 no . 2_465
H10B C10 3.3216 no . 2_565
H10B C11 3.3988 no . 2_565
H10B H6 3.2911 no . 2_465
H10B H10A 2.6001 no . 2_565
H10B H11A 2.7435 no . 2_565
H11A N1 3.0922 no . 1_455
H11A C4 3.5556 no . 2_465
H11A C10 3.5796 no . 2_465
H11A H6 3.5499 no . 1_455
H11A H10B 2.7435 no . 2_465
H11A H14B 3.0228 no . 3_445
H11A H18A 3.1507 no . 1_455
H11B C3 3.3344 no . 2_465
H11B C4 3.3101 no . 2_465
H11B C5 3.1560 no . 2_465
H11B C6 3.0445 no . 2_465
H11B C7 3.0515 no . 2_465
H11B C8 3.2021 no . 2_465
H11B H6 3.4977 no . 2_465
H11B H7 3.4999 no . 2_465
H11B H14B 3.2556 no . 3_445
H12A C3 3.4738 no . 4_475
H12A C8 2.9815 no . 4_475
H12A H3 3.3728 no . 4_475
H12A H8 2.4507 no . 4_475
H12A H14B 3.3548 no . 3_445
H12A H18A 3.4089 no . 3_555
H12B N1 2.8451 no . 1_455
H12B H6 3.2070 no . 1_455
H12B H8 3.2979 no . 4_475
H12B H14B 3.1024 no . 3_445
H12B H17A 3.2051 no . 1_455
H12B H18B 3.3249 no . 3_455
H14A C7 3.2675 no . 2_475
H14A C8 3.1927 no . 2_475
H14A C17 3.4404 no . 3_555
H14A H6 3.0539 no . 1_455
H14A H7 2.7119 no . 2_475
H14A H8 2.5586 no . 2_475
H14A H17A 2.6970 no . 3_555
H14A H17C 3.3232 no . 3_555
H14A H18A 3.3873 no . 3_555
H14B N2 2.5526 no . 3_455
H14B C11 3.1684 no . 3_455
H14B C12 3.2326 no . 3_455
H14B H6 3.1411 no . 1_455
H14B H8 2.9789 no . 2_475
H14B H11A 3.0228 no . 3_455
H14B H11B 3.2556 no . 3_455
H14B H12A 3.3548 no . 3_455
H14B H12B 3.1024 no . 3_455
H14B H17A 3.3503 no . 3_555
H14B H17C 3.3983 no . 3_455
H14B H18A 3.1510 no . 3_555
H14B H18B 3.3662 no . 3_455
H17A C14 3.1825 no . 3_545
H17A H7 2.8307 no . 4_575
H17A H12B 3.2051 no . 1_655
H17A H14A 2.6970 no . 3_545
H17A H14B 3.3503 no . 3_545
H17A H18B 3.1507 no . 3_555
H17B C3 3.4602 no . 4_475
H17B C8 3.5903 no . 4_475
H17B C18 3.1458 no . 3_555
H17B H3 2.8322 no . 4_475
H17B H7 3.3784 no . 4_575
H17B H8 3.0859 no . 4_475
H17B H18A 2.8800 no . 3_555
H17B H18B 2.8408 no . 3_555
H17B H18C 3.1952 no . 3_555
H17C C5 3.2670 no . 3_545
H17C C6 3.1164 no . 3_545
H17C C7 3.3945 no . 3_545
H17C H3 3.2222 no . 4_475
H17C H6 3.3638 no . 3_545
H17C H7 3.3862 no . 4_575
H17C H8 2.9741 no . 4_475
H17C H14A 3.3232 no . 3_545
H17C H14B 3.3983 no . 3_445
H18A C13 3.5392 no . 3_545
H18A C14 3.1744 no . 3_545
H18A H10A 3.5992 no . 2_565
H18A H11A 3.1507 no . 1_655
H18A H12A 3.4089 no . 3_545
H18A H14A 3.3873 no . 3_545
H18A H14B 3.1510 no . 3_545
H18A H17B 2.8800 no . 3_545
H18B N1 3.0802 no . 3_545
H18B C5 3.4954 no . 3_545
H18B C15 3.4484 no . 3_545
H18B C17 3.4008 no . 3_545
H18B H12B 3.3249 no . 3_445
H18B H14B 3.3662 no . 3_445
H18B H17A 3.1507 no . 3_545
H18B H17B 2.8408 no . 3_545
H18C C6 3.3607 no . 2_465
H18C C7 3.3283 no . 2_465
H18C H3 3.5334 no . 2_565
H18C H6 3.3324 no . 2_465
H18C H7 3.2611 no . 2_465
H18C H10A 2.9474 no . 2_565
H18C H17B 3.1952 no . 3_545

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20190307at345-1
_database_code_depnum_ccdc_archive 'CCDC 1905890'
loop_
_audit_author_name
_audit_author_address
'Akira Tsubouchi'
;Tokyo University of Agriculture and Technology
Japan
;
_audit_update_record             
;
2019-03-27 deposited with the CCDC.	2019-04-24 downloaded from the CCDC.
;
_audit_creation_date             2019-03-08
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 N3 O, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C24 H24 N4 O2.50'
_chemical_formula_weight         408.47
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.3214(12)
_cell_length_b                   8.4434(8)
_cell_length_c                   20.5045(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.133(8)
_cell_angle_gamma                90
_cell_volume                     2106.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3901
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.9780
_cell_measurement_theta_min      2.6240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.1350
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21973
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.024
_diffrn_reflns_theta_min         2.614
_diffrn_ambient_temperature      170
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean 6.83
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   58.26    --   30.00  54.00-180.00  193
  2  ω     16.00 119.00   1.00   58.26    --   30.00  54.00-180.00  103
  3  ω      6.00 115.00   1.00   58.26    --   30.00  54.00  90.00  109
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0014728000
_diffrn_orient_matrix_UB_12      -0.0136645000
_diffrn_orient_matrix_UB_13      0.0342479000
_diffrn_orient_matrix_UB_21      0.0582366000
_diffrn_orient_matrix_UB_22      0.0043868000
_diffrn_orient_matrix_UB_23      0.0049915000
_diffrn_orient_matrix_UB_31      -0.0028861000
_diffrn_orient_matrix_UB_32      0.0827383000
_diffrn_orient_matrix_UB_33      0.0054782000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_type              ?
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.913
_reflns_Friedel_fraction_max     0.700
_reflns_number_gt                5418
_reflns_number_total             12924
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 1265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -4.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         12924
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1865
_refine_ls_R_factor_gt           0.0875
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2126
_refine_ls_wR_factor_ref         0.2969
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C00X(H00F,H00G), C00Y(H00H,H00I), C010(H01P,H01Q), C013(H01R,
 H01S), C014(H01A,H01B), C019(H01C,H01D), C01E(H01K,H01L), C01M(H01W,H01X)
2.b Aromatic/amide H refined with riding coordinates:
 N002(H002), N004(H004), N005(H005), N008(H008), C00M(H00M), C00U(H00U),
 C00V(H00V), C00W(H00W), C00Z(H00Z), C011(H011), C012(H012), C015(H015),
 C016(H016), C017(H017), C018(H018), C01A(H01E), C01B(H01F), C01C(H01G),
 C01F(H01M), C01G(H01N), C01I(H01T), C01J(H01U), C01K(H01V), C01L(H01O)
2.c Idealised Me refined as rotating group:
 C00T(H00C,H00D,H00E), C01D(H01H,H01I,H01J), C01N(H01Y,H,HA), C01O(H01Z,HB,HC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O -0.4480(4) -1.4587(5) -0.6659(2) 0.0403(11) Uani 1 1 d . . . . .
N002 N -0.3783(5) -1.2688(7) -0.7707(2) 0.0365(12) Uani 1 1 d . . . . .
H002 H -0.435351 -1.328852 -0.778312 0.044 Uiso 1 1 calc R . . . .
O003 O -0.5664(4) -0.4457(6) -0.8369(2) 0.0443(12) Uani 1 1 d . . . . .
N004 N -0.3937(4) -1.3669(6) -0.5617(2) 0.0371(12) Uani 1 1 d . . . . .
H004 H -0.377877 -1.283327 -0.538144 0.045 Uiso 1 1 calc R . . . .
N005 N -0.6387(4) -0.6401(7) -0.7325(2) 0.0352(12) Uani 1 1 d . . . . .
H005 H -0.581233 -0.580902 -0.725601 0.042 Uiso 1 1 calc R . . . .
N006 N -0.6777(4) -0.8259(7) -0.9025(3) 0.0378(12) Uani 1 1 d . . . . .
O4 O -1.0154(6) -0.4594(9) -0.7572(3) 0.0708(17) Uani 1 1 d . . . . .
N008 N -0.6170(5) -0.5421(7) -0.9412(2) 0.0435(14) Uani 1 1 d . . . . .
H008 H -0.632615 -0.626492 -0.964226 0.052 Uiso 1 1 calc R . . . .
N009 N -0.3370(5) -1.0832(6) -0.5999(3) 0.0393(12) Uani 1 1 d . . . . .
C00A C -0.4164(5) -1.3493(8) -0.6273(3) 0.0340(13) Uani 1 1 d . . . . .
C00B C -0.7073(6) -0.6715(8) -0.6877(3) 0.0366(14) Uani 1 1 d . . . . .
C00C C -0.3424(5) -1.1858(7) -0.7122(3) 0.0347(14) Uani 1 1 d . . . . .
C00D C -0.2820(6) -1.5831(8) -0.5059(3) 0.0400(15) Uani 1 1 d . . . . .
C00E C -0.2240(5) -1.1303(8) -0.7837(3) 0.0362(14) Uani 1 1 d . . . . .
C00F C -0.6165(5) -0.7253(7) -0.8502(3) 0.0332(13) Uani 1 1 d . . . . .
C00G C -0.7678(5) -0.8012(8) -0.7841(3) 0.0375(14) Uani 1 1 d . . . . .
C00H C -0.3056(6) -1.2372(8) -0.8146(3) 0.0382(15) Uani 1 1 d . . . . .
C00I C -0.6001(5) -0.5547(7) -0.8753(3) 0.0331(13) Uani 1 1 d . . . . .
C00J C -0.6767(5) -0.7187(7) -0.7900(3) 0.0317(13) Uani 1 1 d . . . . .
C00K C -0.5060(5) -0.8100(8) -0.8344(3) 0.0381(14) Uani 1 1 d . . . . .
C00L C -0.3987(5) -1.1822(8) -0.6536(3) 0.0371(14) Uani 1 1 d . . . . .
C00M C -0.3076(6) -1.2893(9) -0.8794(3) 0.0471(18) Uani 1 1 d . . . . .
H00M H -0.361024 -1.359144 -0.899421 0.057 Uiso 1 1 calc R . . . .
C00N C -0.7209(5) -0.3185(8) -1.0014(3) 0.0400(15) Uani 1 1 d . . . . .
C00O C -0.3940(6) -1.5172(8) -0.5277(3) 0.0429(16) Uani 1 1 d . . . . .
H00A H -0.436628 -1.592904 -0.556809 0.051 Uiso 1 1 calc R . . . .
H00B H -0.430113 -1.503614 -0.489324 0.051 Uiso 1 1 calc R . . . .
C00P C -0.2457(6) -1.1048(8) -0.7177(3) 0.0384(15) Uani 1 1 d . . . . .
C00Q C -0.7904(6) -0.7736(9) -0.7190(3) 0.0416(16) Uani 1 1 d . . . . .
C00R C -0.5109(6) -1.0997(8) -0.6674(3) 0.0420(16) Uani 1 1 d . . . . .
O00S O -1.0511(5) -0.3973(8) -0.6582(3) 0.0846(19) Uani 1 1 d . . . . .
C00T C -0.4082(5) -0.7429(9) -0.7902(4) 0.0464(17) Uani 1 1 d . . . . .
H00C H -0.394571 -0.637197 -0.804171 0.070 Uiso 1 1 calc GR . . . .
H00D H -0.345009 -0.807804 -0.792717 0.070 Uiso 1 1 calc GR . . . .
H00E H -0.422381 -0.740749 -0.745547 0.070 Uiso 1 1 calc GR . . . .
C00U C -0.7034(6) -0.6188(9) -0.6225(3) 0.0427(16) Uani 1 1 d . . . . .
H00U H -0.649221 -0.549324 -0.603004 0.051 Uiso 1 1 calc R . . . .
C00V C -0.7839(8) -0.6751(11) -0.5887(4) 0.063(2) Uani 1 1 d . . . . .
H00V H -0.783167 -0.643203 -0.545256 0.075 Uiso 1 1 calc R . . . .
C00W C -0.8689(6) -0.8289(10) -0.6822(4) 0.0507(19) Uani 1 1 d . . . . .
H00W H -0.922727 -0.899548 -0.701171 0.061 Uiso 1 1 calc R . . . .
C00X C -0.7972(6) -0.8320(10) -0.9040(3) 0.0466(17) Uani 1 1 d . . . . .
H00F H -0.829388 -0.899085 -0.940438 0.056 Uiso 1 1 calc R . . . .
H00G H -0.827114 -0.726308 -0.912448 0.056 Uiso 1 1 calc R . . . .
C00Y C -0.6224(6) -0.9799(9) -0.9035(3) 0.0510(19) Uani 1 1 d . . . . .
H00H H -0.618339 -1.012886 -0.948348 0.061 Uiso 1 1 calc R . . . .
H00I H -0.660255 -1.060841 -0.882138 0.061 Uiso 1 1 calc R . . . .
C00Z C -0.7350(7) -0.2246(9) -1.0561(4) 0.0522(19) Uani 1 1 d . . . . .
H00Z H -0.675259 -0.211416 -1.078149 0.063 Uiso 1 1 calc R . . . .
C010 C -0.8310(7) -0.8943(10) -0.8405(3) 0.0505(19) Uani 1 1 d . . . . .
H01P H -0.909423 -0.880563 -0.841598 0.061 Uiso 1 1 calc R . . . .
H01Q H -0.813868 -1.006166 -0.835361 0.061 Uiso 1 1 calc R . . . .
C011 C -0.2642(6) -1.6867(9) -0.4510(4) 0.0491(18) Uani 1 1 d . . . . .
H011 H -0.321111 -1.712082 -0.428042 0.059 Uiso 1 1 calc R . . . .
C012 C -0.5121(7) -0.9494(9) -0.8663(3) 0.0478(18) Uani 1 1 d . . . . .
H012 H -0.453228 -1.018961 -0.864926 0.057 Uiso 1 1 calc R . . . .
C013 C -0.6104(5) -0.3923(8) -0.9759(3) 0.0409(16) Uani 1 1 d . . . . .
H01R H -0.571620 -0.409848 -1.012848 0.049 Uiso 1 1 calc R . . . .
H01S H -0.567598 -0.317994 -0.946167 0.049 Uiso 1 1 calc R . . . .
C014 C -0.2188(6) -1.0738(9) -0.5973(3) 0.0477(18) Uani 1 1 d . . . . .
H01A H -0.187576 -1.177492 -0.585934 0.057 Uiso 1 1 calc R . . . .
H01B H -0.189310 -1.001659 -0.562057 0.057 Uiso 1 1 calc R . . . .
C015 C -0.5047(7) -0.9607(10) -0.6379(4) 0.055(2) Uani 1 1 d . . . . .
H015 H -0.563156 -0.890266 -0.640293 0.066 Uiso 1 1 calc R . . . .
C016 C -0.1977(6) -1.5535(9) -0.5392(4) 0.0535(19) Uani 1 1 d . . . . .
H016 H -0.209539 -1.486460 -0.575653 0.064 Uiso 1 1 calc R . . . .
C017 C -0.8670(7) -0.7792(11) -0.6179(4) 0.059(2) Uani 1 1 d . . . . .
H017 H -0.920422 -0.814298 -0.593878 0.071 Uiso 1 1 calc R . . . .
C018 C -0.8114(6) -0.3420(10) -0.9691(4) 0.056(2) Uani 1 1 d . . . . .
H018 H -0.805777 -0.406135 -0.931813 0.068 Uiso 1 1 calc R . . . .
C019 C -0.1807(7) -1.0182(10) -0.6616(3) 0.0528(19) Uani 1 1 d . . . . .
H01C H -0.192108 -0.905000 -0.667213 0.063 Uiso 1 1 calc R . . . .
H01D H -0.103006 -1.040063 -0.659858 0.063 Uiso 1 1 calc R . . . .
C01A C -0.1455(6) -1.1272(9) -0.8834(4) 0.053(2) Uani 1 1 d . . . . .
H01E H -0.092796 -1.090745 -0.907571 0.064 Uiso 1 1 calc R . . . .
C01B C -0.2251(6) -1.2313(9) -0.9126(3) 0.0441(17) Uani 1 1 d . . . . .
H01F H -0.223803 -1.263853 -0.955841 0.053 Uiso 1 1 calc R . . . .
C01C C -0.1421(6) -1.0760(9) -0.8194(3) 0.0494(18) Uani 1 1 d . . . . .
H01G H -0.087230 -1.007373 -0.800126 0.059 Uiso 1 1 calc R . . . .
C01D C -0.6070(6) -1.1686(10) -0.7108(3) 0.056(2) Uani 1 1 d . . . . .
H01H H -0.584843 -1.205394 -0.750943 0.084 Uiso 1 1 calc GR . . . .
H01I H -0.662969 -1.089290 -0.720831 0.084 Uiso 1 1 calc GR . . . .
H01J H -0.635420 -1.255789 -0.688579 0.084 Uiso 1 1 calc GR . . . .
C01E C -0.3921(7) -0.9292(9) -0.6001(4) 0.056(2) Uani 1 1 d . . . . .
H01K H -0.354014 -0.849548 -0.622005 0.067 Uiso 1 1 calc R . . . .
H01L H -0.396151 -0.894289 -0.555520 0.067 Uiso 1 1 calc R . . . .
C01F C -0.0930(7) -1.6204(11) -0.5206(5) 0.069(2) Uani 1 1 d . . . . .
H01M H -0.036264 -1.595448 -0.543846 0.083 Uiso 1 1 calc R . . . .
C01G C -0.1603(7) -1.7495(10) -0.4323(5) 0.064(2) Uani 1 1 d . . . . .
H01N H -0.146896 -1.811927 -0.394537 0.077 Uiso 1 1 calc R . . . .
C01H C -1.0813(6) -0.4742(10) -0.7081(4) 0.059(2) Uani 1 1 d . . . . .
C01I C -0.9176(8) -0.1707(11) -1.0486(5) 0.071(3) Uani 1 1 d . . . . .
H01T H -0.983626 -0.119746 -1.063862 0.085 Uiso 1 1 calc R . . . .
C01J C -0.8296(7) -0.1490(11) -1.0808(5) 0.067(2) Uani 1 1 d . . . . .
H01U H -0.834556 -0.085039 -1.118029 0.081 Uiso 1 1 calc R . . . .
C01K C -0.9093(7) -0.2678(11) -0.9936(5) 0.070(3) Uani 1 1 d . . . . .
H01V H -0.970435 -0.283238 -0.972956 0.083 Uiso 1 1 calc R . . . .
C01L C -0.0747(7) -1.7226(10) -0.4681(5) 0.070(3) Uani 1 1 d . . . . .
H01O H -0.007152 -1.772595 -0.456589 0.084 Uiso 1 1 calc R . . . .
C01M C -0.9218(7) -0.3787(12) -0.7539(5) 0.084(3) Uani 1 1 d . . . . .
H01W H -0.869723 -0.421845 -0.717865 0.101 Uiso 1 1 calc R . . . .
H01X H -0.936023 -0.269914 -0.742630 0.101 Uiso 1 1 calc R . . . .
C01N C -1.1733(8) -0.5754(11) -0.7241(5) 0.086(3) Uani 1 1 d . . . . .
H01Y H -1.231664 -0.519126 -0.750997 0.128 Uiso 1 1 calc GR . . . .
H H -1.197671 -0.609887 -0.684179 0.128 Uiso 1 1 calc GR . . . .
HA H -1.152987 -0.665795 -0.747832 0.128 Uiso 1 1 calc GR . . . .
C01O C -0.8711(9) -0.3768(14) -0.8105(5) 0.101(4) Uani 1 1 d . . . . .
H01Z H -0.896688 -0.465141 -0.838206 0.152 Uiso 1 1 calc GR . . . .
HB H -0.792892 -0.383890 -0.797751 0.152 Uiso 1 1 calc GR . . . .
HC H -0.889170 -0.279948 -0.834331 0.152 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00A 1.239(7) . ?
N002 H002 0.8600 . ?
N002 C00C 1.401(8) . ?
N002 C00H 1.393(8) . ?
O003 C00I 1.240(7) . ?
N004 H004 0.8600 . ?
N004 C00A 1.337(7) . ?
N004 C00O 1.448(8) . ?
N005 H005 0.8600 . ?
N005 C00B 1.369(8) . ?
N005 C00J 1.370(7) . ?
N006 C00F 1.478(8) . ?
N006 C00X 1.470(8) . ?
N006 C00Y 1.470(9) . ?
O4 C01H 1.397(10) . ?
O4 C01M 1.332(11) . ?
N008 H008 0.8600 . ?
N008 C00I 1.337(7) . ?
N008 C013 1.460(8) . ?
N009 C00L 1.492(8) . ?
N009 C014 1.451(8) . ?
N009 C01E 1.466(9) . ?
C00A C00L 1.539(9) . ?
C00B C00Q 1.413(10) . ?
C00B C00U 1.401(9) . ?
C00C C00L 1.479(8) . ?
C00C C00P 1.394(9) . ?
C00D C00O 1.489(9) . ?
C00D C011 1.415(9) . ?
C00D C016 1.354(9) . ?
C00E C00H 1.423(10) . ?
C00E C00P 1.437(9) . ?
C00E C01C 1.414(9) . ?
C00F C00I 1.554(9) . ?
C00F C00J 1.537(8) . ?
C00F C00K 1.527(9) . ?
C00G C00J 1.342(9) . ?
C00G C00Q 1.426(9) . ?
C00G C010 1.509(9) . ?
C00H C00M 1.396(9) . ?
C00K C00T 1.499(9) . ?
C00K C012 1.343(10) . ?
C00L C00R 1.533(9) . ?
C00M H00M 0.9300 . ?
C00M C01B 1.400(10) . ?
C00N C00Z 1.362(10) . ?
C00N C013 1.513(10) . ?
C00N C018 1.399(9) . ?
C00O H00A 0.9700 . ?
C00O H00B 0.9700 . ?
C00P C019 1.485(9) . ?
C00Q C00W 1.398(9) . ?
C00R C015 1.316(11) . ?
C00R C01D 1.483(10) . ?
O00S C01H 1.219(9) . ?
C00T H00C 0.9600 . ?
C00T H00D 0.9600 . ?
C00T H00E 0.9600 . ?
C00U H00U 0.9300 . ?
C00U C00V 1.381(11) . ?
C00V H00V 0.9300 . ?
C00V C017 1.409(12) . ?
C00W H00W 0.9300 . ?
C00W C017 1.381(10) . ?
C00X H00F 0.9700 . ?
C00X H00G 0.9700 . ?
C00X C010 1.522(9) . ?
C00Y H00H 0.9700 . ?
C00Y H00I 0.9700 . ?
C00Y C012 1.472(10) . ?
C00Z H00Z 0.9300 . ?
C00Z C01J 1.355(11) . ?
C010 H01P 0.9700 . ?
C010 H01Q 0.9700 . ?
C011 H011 0.9300 . ?
C011 C01G 1.383(11) . ?
C012 H012 0.9300 . ?
C013 H01R 0.9700 . ?
C013 H01S 0.9700 . ?
C014 H01A 0.9700 . ?
C014 H01B 0.9700 . ?
C014 C019 1.542(10) . ?
C015 H015 0.9300 . ?
C015 C01E 1.501(11) . ?
C016 H016 0.9300 . ?
C016 C01F 1.405(11) . ?
C017 H017 0.9300 . ?
C018 H018 0.9300 . ?
C018 C01K 1.381(11) . ?
C019 H01C 0.9700 . ?
C019 H01D 0.9700 . ?
C01A H01E 0.9300 . ?
C01A C01B 1.381(11) . ?
C01A C01C 1.375(10) . ?
C01B H01F 0.9300 . ?
C01C H01G 0.9300 . ?
C01D H01H 0.9600 . ?
C01D H01I 0.9600 . ?
C01D H01J 0.9600 . ?
C01E H01K 0.9700 . ?
C01E H01L 0.9700 . ?
C01F H01M 0.9300 . ?
C01F C01L 1.371(12) . ?
C01G H01N 0.9300 . ?
C01G C01L 1.395(12) . ?
C01H C01N 1.415(11) . ?
C01I H01T 0.9300 . ?
C01I C01J 1.367(13) . ?
C01I C01K 1.385(13) . ?
C01J H01U 0.9300 . ?
C01K H01V 0.9300 . ?
C01L H01O 0.9300 . ?
C01M H01W 0.9700 . ?
C01M H01X 0.9700 . ?
C01M C01O 1.401(11) . ?
C01N H01Y 0.9600 . ?
C01N H 0.9600 . ?
C01N HA 0.9600 . ?
C01O H01Z 0.9600 . ?
C01O HB 0.9600 . ?
C01O HC 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C N002 H002 126.0 . . ?
C00H N002 H002 126.0 . . ?
C00H N002 C00C 108.0(5) . . ?
C00A N004 H004 117.8 . . ?
C00A N004 C00O 124.4(5) . . ?
C00O N004 H004 117.8 . . ?
C00B N005 H005 125.6 . . ?
C00B N005 C00J 108.7(5) . . ?
C00J N005 H005 125.6 . . ?
C00X N006 C00F 115.4(5) . . ?
C00X N006 C00Y 115.7(6) . . ?
C00Y N006 C00F 109.5(5) . . ?
C01M O4 C01H 127.4(8) . . ?
C00I N008 H008 118.3 . . ?
C00I N008 C013 123.3(6) . . ?
C013 N008 H008 118.3 . . ?
C014 N009 C00L 116.6(5) . . ?
C014 N009 C01E 114.4(6) . . ?
C01E N009 C00L 108.2(5) . . ?
O001 C00A N004 123.6(6) . . ?
O001 C00A C00L 120.5(5) . . ?
N004 C00A C00L 115.9(5) . . ?
N005 C00B C00Q 107.0(5) . . ?
N005 C00B C00U 130.3(7) . . ?
C00U C00B C00Q 122.7(6) . . ?
N002 C00C C00L 125.5(6) . . ?
C00P C00C N002 109.5(6) . . ?
C00P C00C C00L 124.9(6) . . ?
C011 C00D C00O 119.3(6) . . ?
C016 C00D C00O 121.9(6) . . ?
C016 C00D C011 118.7(7) . . ?
C00H C00E C00P 106.9(6) . . ?
C01C C00E C00H 119.1(6) . . ?
C01C C00E C00P 134.0(7) . . ?
N006 C00F C00I 111.7(5) . . ?
N006 C00F C00J 110.4(5) . . ?
N006 C00F C00K 102.6(5) . . ?
C00J C00F C00I 109.8(5) . . ?
C00K C00F C00I 110.2(5) . . ?
C00K C00F C00J 112.0(5) . . ?
C00J C00G C00Q 106.9(6) . . ?
C00J C00G C010 122.5(6) . . ?
C00Q C00G C010 130.5(6) . . ?
N002 C00H C00E 108.4(5) . . ?
N002 C00H C00M 129.7(7) . . ?
C00M C00H C00E 121.9(6) . . ?
O003 C00I N008 124.5(6) . . ?
O003 C00I C00F 121.6(5) . . ?
N008 C00I C00F 113.7(6) . . ?
N005 C00J C00F 124.5(5) . . ?
C00G C00J N005 110.5(6) . . ?
C00G C00J C00F 124.8(6) . . ?
C00T C00K C00F 123.7(6) . . ?
C012 C00K C00F 109.2(6) . . ?
C012 C00K C00T 127.1(7) . . ?
N009 C00L C00A 109.7(5) . . ?
N009 C00L C00R 102.7(5) . . ?
C00C C00L N009 111.2(5) . . ?
C00C C00L C00A 112.1(5) . . ?
C00C C00L C00R 112.7(5) . . ?
C00R C00L C00A 107.9(5) . . ?
C00H C00M H00M 121.7 . . ?
C00H C00M C01B 116.7(7) . . ?
C01B C00M H00M 121.7 . . ?
C00Z C00N C013 121.0(6) . . ?
C00Z C00N C018 117.7(7) . . ?
C018 C00N C013 121.3(6) . . ?
N004 C00O C00D 113.5(6) . . ?
N004 C00O H00A 108.9 . . ?
N004 C00O H00B 108.9 . . ?
C00D C00O H00A 108.9 . . ?
C00D C00O H00B 108.9 . . ?
H00A C00O H00B 107.7 . . ?
C00C C00P C00E 107.0(6) . . ?
C00C C00P C019 122.8(6) . . ?
C00E C00P C019 130.1(6) . . ?
C00B C00Q C00G 106.9(6) . . ?
C00W C00Q C00B 118.2(6) . . ?
C00W C00Q C00G 134.9(7) . . ?
C015 C00R C00L 109.6(7) . . ?
C015 C00R C01D 127.5(7) . . ?
C01D C00R C00L 122.9(6) . . ?
C00K C00T H00C 109.5 . . ?
C00K C00T H00D 109.5 . . ?
C00K C00T H00E 109.5 . . ?
H00C C00T H00D 109.5 . . ?
H00C C00T H00E 109.5 . . ?
H00D C00T H00E 109.5 . . ?
C00B C00U H00U 121.6 . . ?
C00V C00U C00B 116.7(7) . . ?
C00V C00U H00U 121.6 . . ?
C00U C00V H00V 118.9 . . ?
C00U C00V C017 122.3(7) . . ?
C017 C00V H00V 118.9 . . ?
C00Q C00W H00W 119.8 . . ?
C017 C00W C00Q 120.4(8) . . ?
C017 C00W H00W 119.8 . . ?
N006 C00X H00F 108.8 . . ?
N006 C00X H00G 108.8 . . ?
N006 C00X C010 113.8(6) . . ?
H00F C00X H00G 107.7 . . ?
C010 C00X H00F 108.8 . . ?
C010 C00X H00G 108.8 . . ?
N006 C00Y H00H 111.1 . . ?
N006 C00Y H00I 111.1 . . ?
N006 C00Y C012 103.3(6) . . ?
H00H C00Y H00I 109.1 . . ?
C012 C00Y H00H 111.1 . . ?
C012 C00Y H00I 111.1 . . ?
C00N C00Z H00Z 117.6 . . ?
C01J C00Z C00N 124.9(9) . . ?
C01J C00Z H00Z 117.6 . . ?
C00G C010 C00X 107.3(6) . . ?
C00G C010 H01P 110.2 . . ?
C00G C010 H01Q 110.2 . . ?
C00X C010 H01P 110.2 . . ?
C00X C010 H01Q 110.2 . . ?
H01P C010 H01Q 108.5 . . ?
C00D C011 H011 120.7 . . ?
C01G C011 C00D 118.5(8) . . ?
C01G C011 H011 120.7 . . ?
C00K C012 C00Y 112.4(7) . . ?
C00K C012 H012 123.8 . . ?
C00Y C012 H012 123.8 . . ?
N008 C013 C00N 114.1(6) . . ?
N008 C013 H01R 108.7 . . ?
N008 C013 H01S 108.7 . . ?
C00N C013 H01R 108.7 . . ?
C00N C013 H01S 108.7 . . ?
H01R C013 H01S 107.6 . . ?
N009 C014 H01A 108.5 . . ?
N009 C014 H01B 108.5 . . ?
N009 C014 C019 115.2(5) . . ?
H01A C014 H01B 107.5 . . ?
C019 C014 H01A 108.5 . . ?
C019 C014 H01B 108.5 . . ?
C00R C015 H015 123.9 . . ?
C00R C015 C01E 112.1(7) . . ?
C01E C015 H015 123.9 . . ?
C00D C016 H016 118.9 . . ?
C00D C016 C01F 122.3(8) . . ?
C01F C016 H016 118.9 . . ?
C00V C017 H017 120.2 . . ?
C00W C017 C00V 119.7(8) . . ?
C00W C017 H017 120.2 . . ?
C00N C018 H018 120.7 . . ?
C01K C018 C00N 118.6(8) . . ?
C01K C018 H018 120.7 . . ?
C00P C019 C014 108.2(6) . . ?
C00P C019 H01C 110.1 . . ?
C00P C019 H01D 110.1 . . ?
C014 C019 H01C 110.1 . . ?
C014 C019 H01D 110.1 . . ?
H01C C019 H01D 108.4 . . ?
C01B C01A H01E 119.1 . . ?
C01C C01A H01E 119.1 . . ?
C01C C01A C01B 121.8(7) . . ?
C00M C01B H01F 119.0 . . ?
C01A C01B C00M 122.1(7) . . ?
C01A C01B H01F 119.0 . . ?
C00E C01C H01G 120.8 . . ?
C01A C01C C00E 118.4(7) . . ?
C01A C01C H01G 120.8 . . ?
C00R C01D H01H 109.5 . . ?
C00R C01D H01I 109.5 . . ?
C00R C01D H01J 109.5 . . ?
H01H C01D H01I 109.5 . . ?
H01H C01D H01J 109.5 . . ?
H01I C01D H01J 109.5 . . ?
N009 C01E C015 103.5(6) . . ?
N009 C01E H01K 111.1 . . ?
N009 C01E H01L 111.1 . . ?
C015 C01E H01K 111.1 . . ?
C015 C01E H01L 111.1 . . ?
H01K C01E H01L 109.0 . . ?
C016 C01F H01M 120.2 . . ?
C01L C01F C016 119.7(8) . . ?
C01L C01F H01M 120.2 . . ?
C011 C01G H01N 118.8 . . ?
C011 C01G C01L 122.4(8) . . ?
C01L C01G H01N 118.8 . . ?
O4 C01H C01N 115.1(8) . . ?
O00S C01H O4 115.0(8) . . ?
O00S C01H C01N 129.9(9) . . ?
C01J C01I H01T 119.6 . . ?
C01J C01I C01K 120.7(9) . . ?
C01K C01I H01T 119.6 . . ?
C00Z C01J C01I 117.3(9) . . ?
C00Z C01J H01U 121.4 . . ?
C01I C01J H01U 121.4 . . ?
C018 C01K C01I 120.8(9) . . ?
C018 C01K H01V 119.6 . . ?
C01I C01K H01V 119.6 . . ?
C01F C01L C01G 118.2(8) . . ?
C01F C01L H01O 120.9 . . ?
C01G C01L H01O 120.9 . . ?
O4 C01M H01W 108.0 . . ?
O4 C01M H01X 108.0 . . ?
O4 C01M C01O 117.3(11) . . ?
H01W C01M H01X 107.2 . . ?
C01O C01M H01W 108.0 . . ?
C01O C01M H01X 108.0 . . ?
C01H C01N H01Y 109.5 . . ?
C01H C01N H 109.5 . . ?
C01H C01N HA 109.5 . . ?
H01Y C01N H 109.5 . . ?
H01Y C01N HA 109.5 . . ?
H C01N HA 109.5 . . ?
C01M C01O H01Z 109.5 . . ?
C01M C01O HB 109.5 . . ?
C01M C01O HC 109.5 . . ?
H01Z C01O HB 109.5 . . ?
H01Z C01O HC 109.5 . . ?
HB C01O HC 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.061
_oxdiff_exptl_absorpt_empirical_full_min 0.911
