# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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 
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data_mo_171225k_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1859465'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-10-23 downloaded from the CCDC.
;
_audit_creation_date             2018-08-01
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H4 O, C22 H13 N3 O2'
_chemical_formula_sum            'C23 H17 N3 O3'
_chemical_formula_weight         383.39
_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                   10.830(8)
_cell_length_b                   7.650(6)
_cell_length_c                   12.063(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.07(3)
_cell_angle_gamma                90
_cell_volume                     973.5(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4816
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6755
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1359 before and 0.0613 after correction.
The Ratio of minimum to maximum transmission is 0.9060.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12044
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.872
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                2828
_reflns_number_total             3285
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.558
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.246
_refine_ls_abs_structure_details 
;
 Flack x determined using 1063 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.126
_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)+(0.0712P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C14(H14), C7(H7), C20(H20), C3(H3), C8(H8), C15(H15),
 C9(H9), C18(H18), C16(H16), C17(H17), N1(H1)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_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
O3 O -0.8734(2) -0.2143(4) -0.9695(2) 0.0592(7) Uani 1 1 d . . . . .
H3A H -0.898598 -0.170507 -1.032664 0.089 Uiso 1 1 calc GR . . . .
N2 N -0.0875(2) -0.5507(3) -0.80641(18) 0.0318(6) Uani 1 1 d . . . . .
N3 N -0.1177(2) -0.4471(4) -0.59059(19) 0.0369(6) Uani 1 1 d . . . . .
C11 C 0.1881(3) -0.7710(4) -0.6583(3) 0.0393(8) Uani 1 1 d . . . . .
H11 H 0.161670 -0.793665 -0.591528 0.047 Uiso 1 1 calc R . . . .
C6 C 0.1229(2) -0.6501(4) -0.7358(2) 0.0311(6) Uani 1 1 d . . . . .
C4 C -0.2003(3) -0.4842(4) -0.7919(2) 0.0315(7) Uani 1 1 d . . . . .
C10 C 0.2922(3) -0.8578(5) -0.6798(3) 0.0507(9) Uani 1 1 d . . . . .
H10 H 0.335033 -0.939122 -0.627741 0.061 Uiso 1 1 calc R . . . .
C5 C 0.0065(3) -0.5628(4) -0.7174(2) 0.0300(6) Uani 1 1 d . . . . .
C22 C -0.5610(3) -0.3025(4) -0.7687(3) 0.0403(7) Uani 1 1 d . . . . .
C14 C 0.2127(3) -0.4005(5) -0.5238(3) 0.0476(9) Uani 1 1 d . . . . .
H14 H 0.223775 -0.378650 -0.596737 0.057 Uiso 1 1 calc R . . . .
C7 C 0.1645(3) -0.6173(4) -0.8361(2) 0.0372(7) Uani 1 1 d . . . . .
H7 H 0.121415 -0.537454 -0.889102 0.045 Uiso 1 1 calc R . . . .
C19 C -0.2169(3) -0.4416(4) -0.6811(2) 0.0315(7) Uani 1 1 d . . . . .
C20 C -0.3352(3) -0.3825(5) -0.6652(2) 0.0391(7) Uani 1 1 d . . . . .
H20 H -0.347324 -0.356898 -0.593057 0.047 Uiso 1 1 calc R . . . .
C3 C -0.3002(3) -0.4635(5) -0.8867(2) 0.0388(7) Uani 1 1 d . . . . .
H3 H -0.290723 -0.489642 -0.959601 0.047 Uiso 1 1 calc R . . . .
C8 C 0.2695(3) -0.7040(5) -0.8556(3) 0.0477(9) Uani 1 1 d . . . . .
H8 H 0.297531 -0.680851 -0.921531 0.057 Uiso 1 1 calc R . . . .
C12 C -0.0067(3) -0.4975(4) -0.6069(2) 0.0316(7) Uani 1 1 d . . . . .
C21 C -0.4292(3) -0.3647(4) -0.7577(2) 0.0355(7) Uani 1 1 d . . . . .
C15 C 0.3079(3) -0.3618(6) -0.4307(3) 0.0601(10) Uani 1 1 d . . . . .
H15 H 0.383435 -0.313169 -0.440491 0.072 Uiso 1 1 calc R . . . .
C9 C 0.3329(3) -0.8243(5) -0.7785(3) 0.0544(10) Uani 1 1 d . . . . .
H9 H 0.402907 -0.882967 -0.792725 0.065 Uiso 1 1 calc R . . . .
C18 C 0.0837(3) -0.5043(5) -0.3994(3) 0.0455(9) Uani 1 1 d . . . . .
H18 H 0.007740 -0.550935 -0.389036 0.055 Uiso 1 1 calc R . . . .
C13 C 0.1003(3) -0.4720(4) -0.5088(2) 0.0353(7) Uani 1 1 d . . . . .
C16 C 0.2911(4) -0.3952(6) -0.3229(3) 0.0648(12) Uani 1 1 d . . . . .
H16 H 0.355752 -0.368961 -0.260144 0.078 Uiso 1 1 calc R . . . .
C17 C 0.1800(4) -0.4670(6) -0.3068(3) 0.0594(11) Uani 1 1 d . . . . .
H17 H 0.170076 -0.490087 -0.233660 0.071 Uiso 1 1 calc R . . . .
C1 C -0.5332(3) -0.3671(5) -0.9492(3) 0.0484(9) Uani 1 1 d . . . . .
C2 C -0.4123(3) -0.4037(4) -0.8684(2) 0.0370(7) Uani 1 1 d . . . . .
C23 C -0.9390(3) -0.1368(6) -0.8912(3) 0.0628(11) Uani 1 1 d . . . . .
H23A H -1.024791 -0.178556 -0.906929 0.094 Uiso 1 1 calc GR . . . .
H23B H -0.938991 -0.011942 -0.899249 0.094 Uiso 1 1 calc GR . . . .
H23C H -0.897130 -0.167916 -0.814826 0.094 Uiso 1 1 calc GR . . . .
O1 O -0.6141(2) -0.2595(4) -0.6946(2) 0.0571(7) Uani 1 1 d . . . . .
O2 O -0.5590(2) -0.3886(6) -1.0509(2) 0.0825(12) Uani 1 1 d . . . . .
N1 N -0.6147(2) -0.3057(4) -0.8847(2) 0.0460(7) Uani 1 1 d . . . . .
H1 H -0.691119 -0.272817 -0.913627 0.055 Uiso 1 1 calc R . . . .


_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
O3 H3A 0.8200 . ?
O3 C23 1.433(4) . ?
N2 C4 1.370(4) . ?
N2 C5 1.305(3) . ?
N3 C19 1.348(4) . ?
N3 C12 1.318(4) . ?
C11 H11 0.9300 . ?
C11 C6 1.390(4) . ?
C11 C10 1.382(5) . ?
C6 C5 1.487(4) . ?
C6 C7 1.405(4) . ?
C4 C19 1.426(4) . ?
C4 C3 1.394(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.384(5) . ?
C5 C12 1.460(4) . ?
C22 C21 1.481(4) . ?
C22 O1 1.212(4) . ?
C22 N1 1.389(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(5) . ?
C14 C13 1.383(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(4) . ?
C19 C20 1.413(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.336(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.361(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(6) . ?
C12 C13 1.471(4) . ?
C21 C2 1.419(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(6) . ?
C9 H9 0.9300 . ?
C18 H18 0.9300 . ?
C18 C13 1.394(4) . ?
C18 C17 1.374(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(6) . ?
C17 H17 0.9300 . ?
C1 C2 1.472(4) . ?
C1 O2 1.206(4) . ?
C1 N1 1.384(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 H1 0.8600 . ?

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
C23 O3 H3A 109.5 . . ?
C5 N2 C4 118.2(2) . . ?
C12 N3 C19 118.3(2) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C6 120.4(3) . . ?
C11 C6 C5 121.2(3) . . ?
C11 C6 C7 119.0(3) . . ?
C7 C6 C5 119.7(3) . . ?
N2 C4 C19 120.6(2) . . ?
N2 C4 C3 119.1(2) . . ?
C3 C4 C19 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
N2 C5 C6 116.0(2) . . ?
N2 C5 C12 120.5(2) . . ?
C12 C5 C6 123.5(2) . . ?
O1 C22 C21 129.0(3) . . ?
O1 C22 N1 125.9(3) . . ?
N1 C22 C21 105.0(2) . . ?
C15 C14 H14 120.0 . . ?
C15 C14 C13 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
N3 C19 C4 120.4(3) . . ?
N3 C19 C20 118.8(2) . . ?
C20 C19 C4 120.7(3) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 C19 117.5(3) . . ?
C21 C20 H20 121.2 . . ?
C4 C3 H3 121.3 . . ?
C2 C3 C4 117.4(3) . . ?
C2 C3 H3 121.3 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
N3 C12 C5 121.2(3) . . ?
N3 C12 C13 114.8(2) . . ?
C5 C12 C13 123.9(2) . . ?
C20 C21 C22 130.0(3) . . ?
C20 C21 C2 121.9(3) . . ?
C2 C21 C22 108.1(3) . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.7(4) . . ?
C16 C15 H15 120.1 . . ?
C10 C9 H9 120.1 . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9 120.1 . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C13 119.7(3) . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 C18 120.0(3) . . ?
C18 C13 C12 119.4(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
O2 C1 C2 127.9(3) . . ?
O2 C1 N1 126.0(3) . . ?
N1 C1 C2 106.0(3) . . ?
C3 C2 C21 122.2(3) . . ?
C3 C2 C1 130.4(3) . . ?
C21 C2 C1 107.4(3) . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 N1 H1 123.3 . . ?
C1 N1 C22 113.4(3) . . ?
C1 N1 H1 123.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
