# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_songyongxiang_sx-terb2_collect
_audit_block_doi                 10.5517/ccdc.csd.cc2g7x2q
_database_code_depnum_ccdc_archive 'CCDC 2271713'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4SC01208A 2024
loop_
_audit_author_name
_audit_author_address
'Yongxiang Song'
;South China Sea Institute of Oceanology, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-06-22 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_audit_creation_date             2020-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H44 N2 O6 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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                   6.36910(10)
_cell_length_b                   12.0175(2)
_cell_length_c                   9.0830(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.989(2)
_cell_angle_gamma                90
_cell_volume                     657.39(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5095
_cell_measurement_temperature    106(2)
_cell_measurement_theta_max      73.8160
_cell_measurement_theta_min      5.1570
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6277
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.370
_diffrn_reflns_theta_min         5.150
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(2)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  26.00   0.50    0.50    --    0.00 -82.00  60.00   78
  2  ω    -32.00  27.00   0.50    0.50    --    0.00 -82.00   0.00  118
  3  ω    -13.00  25.00   0.50    0.50    --    0.00 -77.00 120.00   76
  4  ω    -42.00 -15.00   0.50    0.50    --    0.00 -77.00 120.00   54
  5  ω     21.00  55.00   0.50    0.50    --   40.00  65.00 -30.02   68
  6  ω     32.00  69.00   0.50    0.50    --   52.00  75.00  11.86   74
  7  ω     41.00  72.00   0.50    0.50    --   68.00  74.00 -49.07   62
  8  ω    121.00 157.00   0.50    0.50    --   68.00  74.00 -49.07   72
  9  ω     54.00  79.00   0.50    0.50    --   80.00  71.00 -61.26   50
 10  ω     78.00 179.00   0.50    0.50    --   95.80  45.00  60.00  202
 11  ω     77.00 177.00   0.50    0.50    --   95.80  45.00  30.00  200
 12  ω     42.00 125.00   0.50    0.50    --   95.80 -82.00-150.00  166
 13  ω     74.00 117.00   0.50    0.50    --   95.80  54.00  -6.05   86
 14  ω      7.00  39.00   0.50    0.50    --   95.80 -82.00-150.00   64
 15  ω     73.00 132.00   0.50    0.50    --   95.80  61.00 -30.00  118
 16  ω     71.00 161.00   0.50    0.50    --   95.80  68.00 -60.60  180
 17  ω     46.00  86.00   0.50    0.50    --   95.80 -30.00-150.00   80
 18  ω    106.00 184.00   0.50    0.50    --   95.80  30.00 -90.00  156
 19  ω     72.00  97.00   0.50    0.50    --   95.80  61.00 -90.00   50
 20  ω     74.00 180.00   0.50    0.50    --   95.80  61.00 120.00  212
 21  ω     83.00 110.00   0.50    0.50    --   95.80  52.00 -62.70   54
 22  ω    103.00 171.00   0.50    0.50    --   95.80  82.00  90.00  136
 23  ω    121.00 173.00   0.50    0.50    --   95.80  54.00  -6.05  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0312757000
_diffrn_orient_matrix_UB_12      -0.0324910000
_diffrn_orient_matrix_UB_13      0.1699190000
_diffrn_orient_matrix_UB_21      -0.2295963000
_diffrn_orient_matrix_UB_22      0.0491880000
_diffrn_orient_matrix_UB_23      -0.0156952000
_diffrn_orient_matrix_UB_31      -0.1083096000
_diffrn_orient_matrix_UB_32      -0.1138032000
_diffrn_orient_matrix_UB_33      -0.0553840000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                2496
_reflns_number_total             2560
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (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         0.126
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1132 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.069
_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)+(0.0422P)²+0.0844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0737
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C11(H11), C4(H4), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C9(H9A,H9B), C10(H10A,H10B), C3(H3A,H3B)
2.c X=CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O17(H17), O13(H13)
;
_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
O17 O 0.9841(2) 0.59979(11) 0.56347(15) 0.0246(3) Uani 1 1 d . . . . .
H17 H 0.9816 0.5385 0.5233 0.037 Uiso 1 1 calc GR . . . .
O14 O 0.8824(2) 0.38781(11) 0.40986(17) 0.0279(3) Uani 1 1 d . . . . .
O13 O 0.6710(2) 0.23725(11) 0.32704(18) 0.0315(3) Uani 1 1 d . . . . .
H13 H 0.7880 0.2047 0.3704 0.047 Uiso 1 1 calc GR . . . .
C1 C 0.4840(3) 0.52881(13) 0.33102(19) 0.0179(4) Uani 1 1 d . . . . .
C5 C 0.5917(3) 0.55293(14) 0.5023(2) 0.0212(4) Uani 1 1 d . . . . .
C7 C 0.7014(3) 0.34616(15) 0.3484(2) 0.0219(4) Uani 1 1 d . . . . .
C2 C 0.6145(3) 0.59745(15) 0.24670(19) 0.0190(3) Uani 1 1 d . . . . .
H2 H 0.7437 0.5544 0.2438 0.023 Uiso 1 1 calc R . . . .
C11 C 0.4463(3) 0.60343(15) 0.0816(2) 0.0216(4) Uani 1 1 d . . . . .
H11 H 0.4902 0.6593 0.0186 0.026 Uiso 1 1 calc R . . . .
C12 C 0.2453(3) 0.58044(14) 0.2650(2) 0.0197(4) Uani 1 1 d . . . . .
H12A H 0.1338 0.5230 0.2525 0.024 Uiso 1 1 calc R . . . .
H12B H 0.2244 0.6363 0.3361 0.024 Uiso 1 1 calc R . . . .
C4 C 0.7623(3) 0.64448(15) 0.5185(2) 0.0236(4) Uani 1 1 d . . . . .
H4 H 0.7511 0.6994 0.5953 0.028 Uiso 1 1 calc R . . . .
C13 C 0.2221(3) 0.63445(15) 0.1041(2) 0.0215(4) Uani 1 1 d . . . . .
C6 C 0.5411(3) 0.50633(17) 0.6185(2) 0.0278(4) Uani 1 1 d . . . . .
H6A H 0.4293 0.4531 0.5979 0.033 Uiso 1 1 calc R . . . .
H6B H 0.6174 0.5268 0.7207 0.033 Uiso 1 1 calc R . . . .
C9 C 0.3771(3) 0.39360(15) 0.1068(2) 0.0244(4) Uani 1 1 d . . . . .
H9A H 0.4217 0.3223 0.0765 0.029 Uiso 1 1 calc R . . . .
H9B H 0.2166 0.3932 0.0787 0.029 Uiso 1 1 calc R . . . .
C8 C 0.4785(3) 0.40546(14) 0.2861(2) 0.0201(4) Uani 1 1 d . . . . .
H8 H 0.3770 0.3681 0.3313 0.024 Uiso 1 1 calc R . . . .
C14 C 0.0165(3) 0.59411(18) -0.0273(2) 0.0266(4) Uani 1 1 d . . . . .
H14A H 0.0205 0.6227 -0.1250 0.040 Uiso 1 1 calc GR . . . .
H14B H -0.1152 0.6202 -0.0087 0.040 Uiso 1 1 calc GR . . . .
H14C H 0.0156 0.5143 -0.0303 0.040 Uiso 1 1 calc GR . . . .
C10 C 0.4447(3) 0.48549(16) 0.0138(2) 0.0254(4) Uani 1 1 d . . . . .
H10A H 0.3428 0.4846 -0.0922 0.030 Uiso 1 1 calc R . . . .
H10B H 0.5918 0.4690 0.0097 0.030 Uiso 1 1 calc R . . . .
C3 C 0.6951(3) 0.69757(15) 0.3565(2) 0.0247(4) Uani 1 1 d . . . . .
H3A H 0.8207 0.7338 0.3385 0.030 Uiso 1 1 calc R . . . .
H3B H 0.5771 0.7516 0.3432 0.030 Uiso 1 1 calc R . . . .
C15 C 0.1940(3) 0.76213(16) 0.1056(2) 0.0286(4) Uani 1 1 d . . . . .
H15A H 0.3279 0.7950 0.1734 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.0726 0.7800 0.1422 0.043 Uiso 1 1 calc GR . . . .
H15C H 0.1640 0.7907 0.0021 0.043 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
O17 H17 0.8200 . ?
O17 C4 1.441(2) . ?
O14 C7 1.214(2) . ?
O13 H13 0.8200 . ?
O13 C7 1.328(2) . ?
C1 C5 1.510(2) . ?
C1 C2 1.540(2) . ?
C1 C12 1.570(2) . ?
C1 C8 1.535(2) . ?
C5 C4 1.519(3) . ?
C5 C6 1.324(3) . ?
C7 C8 1.524(2) . ?
C2 H2 0.9800 . ?
C2 C11 1.535(2) . ?
C2 C3 1.540(3) . ?
C11 H11 0.9800 . ?
C11 C13 1.553(2) . ?
C11 C10 1.544(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.561(2) . ?
C4 H4 0.9800 . ?
C4 C3 1.532(3) . ?
C13 C14 1.535(2) . ?
C13 C15 1.545(2) . ?
C6 H6A 0.9300 . ?
C6 H6B 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.551(3) . ?
C9 C10 1.535(3) . ?
C8 H8 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C4 O17 H17 109.5 . . ?
C7 O13 H13 109.5 . . ?
C5 C1 C2 105.79(14) . . ?
C5 C1 C12 112.12(14) . . ?
C5 C1 C8 115.01(14) . . ?
C2 C1 C12 102.15(13) . . ?
C8 C1 C2 110.78(14) . . ?
C8 C1 C12 110.14(13) . . ?
C1 C5 C4 108.00(15) . . ?
C6 C5 C1 126.39(17) . . ?
C6 C5 C4 125.55(17) . . ?
O14 C7 O13 123.05(17) . . ?
O14 C7 C8 127.52(16) . . ?
O13 C7 C8 109.43(15) . . ?
C1 C2 H2 108.9 . . ?
C1 C2 C3 102.51(14) . . ?
C11 C2 C1 101.13(13) . . ?
C11 C2 H2 108.9 . . ?
C11 C2 C3 125.14(15) . . ?
C3 C2 H2 108.9 . . ?
C2 C11 H11 111.2 . . ?
C2 C11 C13 105.21(14) . . ?
C2 C11 C10 105.01(14) . . ?
C13 C11 H11 111.2 . . ?
C10 C11 H11 111.2 . . ?
C10 C11 C13 112.70(15) . . ?
C1 C12 H12A 110.1 . . ?
C1 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 C1 107.87(14) . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
O17 C4 C5 111.21(14) . . ?
O17 C4 H4 109.9 . . ?
O17 C4 C3 111.68(16) . . ?
C5 C4 H4 109.9 . . ?
C5 C4 C3 103.98(14) . . ?
C3 C4 H4 109.9 . . ?
C11 C13 C12 102.25(13) . . ?
C14 C13 C11 114.24(15) . . ?
C14 C13 C12 113.16(15) . . ?
C14 C13 C15 104.38(15) . . ?
C15 C13 C11 110.71(15) . . ?
C15 C13 C12 112.37(16) . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
H9A C9 H9B 107.6 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C10 C9 C8 114.63(15) . . ?
C1 C8 C9 109.49(14) . . ?
C1 C8 H8 107.0 . . ?
C7 C8 C1 114.51(14) . . ?
C7 C8 C9 111.45(14) . . ?
C7 C8 H8 107.0 . . ?
C9 C8 H8 107.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 C11 114.03(15) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 C2 103.10(14) . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O17 C4 C3 C2 83.54(17) . . . . ?
O14 C7 C8 C1 -10.4(3) . . . . ?
O14 C7 C8 C9 114.6(2) . . . . ?
O13 C7 C8 C1 168.99(15) . . . . ?
O13 C7 C8 C9 -66.04(19) . . . . ?
C1 C5 C4 O17 -101.94(16) . . . . ?
C1 C5 C4 C3 18.39(18) . . . . ?
C1 C2 C11 C13 46.18(17) . . . . ?
C1 C2 C11 C10 -72.96(16) . . . . ?
C1 C2 C3 C4 40.52(17) . . . . ?
C1 C12 C13 C11 3.66(18) . . . . ?
C1 C12 C13 C14 127.02(16) . . . . ?
C1 C12 C13 C15 -115.07(16) . . . . ?
C5 C1 C2 C11 -159.36(14) . . . . ?
C5 C1 C2 C3 -29.24(17) . . . . ?
C5 C1 C12 C13 136.71(15) . . . . ?
C5 C1 C8 C7 -50.6(2) . . . . ?
C5 C1 C8 C9 -176.56(15) . . . . ?
C5 C4 C3 C2 -36.47(17) . . . . ?
C2 C1 C5 C4 6.92(18) . . . . ?
C2 C1 C5 C6 -175.68(18) . . . . ?
C2 C1 C12 C13 23.89(17) . . . . ?
C2 C1 C8 C7 69.32(18) . . . . ?
C2 C1 C8 C9 -56.69(17) . . . . ?
C2 C11 C13 C12 -30.46(17) . . . . ?
C2 C11 C13 C14 -153.08(15) . . . . ?
C2 C11 C13 C15 89.44(18) . . . . ?
C2 C11 C10 C9 59.67(19) . . . . ?
C11 C2 C3 C4 153.97(16) . . . . ?
C12 C1 C5 C4 -103.63(16) . . . . ?
C12 C1 C5 C6 73.8(2) . . . . ?
C12 C1 C2 C11 -41.90(16) . . . . ?
C12 C1 C2 C3 88.22(15) . . . . ?
C12 C1 C8 C7 -178.41(14) . . . . ?
C12 C1 C8 C9 55.59(18) . . . . ?
C13 C11 C10 C9 -54.3(2) . . . . ?
C6 C5 C4 O17 80.6(2) . . . . ?
C6 C5 C4 C3 -159.04(18) . . . . ?
C8 C1 C5 C4 129.52(15) . . . . ?
C8 C1 C5 C6 -53.1(2) . . . . ?
C8 C1 C2 C11 75.39(16) . . . . ?
C8 C1 C2 C3 -154.49(14) . . . . ?
C8 C1 C12 C13 -93.86(16) . . . . ?
C8 C9 C10 C11 -41.7(2) . . . . ?
C10 C11 C13 C12 83.41(17) . . . . ?
C10 C11 C13 C14 -39.2(2) . . . . ?
C10 C11 C13 C15 -156.69(15) . . . . ?
C10 C9 C8 C1 38.1(2) . . . . ?
C10 C9 C8 C7 -89.60(18) . . . . ?
C3 C2 C11 C13 -67.9(2) . . . . ?
C3 C2 C11 C10 172.94(17) . . . . ?

_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 1.123
_oxdiff_exptl_absorpt_empirical_full_min 0.907
####################################################################### 
# 
# 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_songyongxiang_xs-terb_collect
_audit_block_doi                 10.5517/ccdc.csd.cc2g7x3r
_database_code_depnum_ccdc_archive 'CCDC 2271714'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4SC01208A 2024
loop_
_audit_author_name
_audit_author_address
'Yongxiang Song'
;South China Sea Institute of Oceanology, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-06-22 deposited with the CCDC.	2024-05-14 downloaded from the CCDC.
;
_audit_creation_date             2023-01-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C66 H60 N6 O6 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.45480(10)
_cell_length_b                   17.2854(3)
_cell_length_c                   12.2879(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1371.01(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9604
_cell_measurement_temperature    106(5)
_cell_measurement_theta_max      74.0950
_cell_measurement_theta_min      4.4220
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.801
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12582
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.579
_diffrn_reflns_theta_max         66.579
_diffrn_reflns_theta_min         4.415
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(5)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  14.00   0.50    2.00    --    0.00 -82.00-150.00   56
  2  ω    -29.00  21.00   0.50    2.00    --    0.00 -82.00 -90.00  100
  3  ω      8.00  89.00   0.50    2.00    --    0.00  38.00  60.00  162
  4  ω    -28.00   0.00   0.50    2.00    --    0.00 -82.00  60.00   56
  5  ω    -29.00  -4.00   0.50    2.00    --    0.00 -82.00   0.00   50
  6  ω    -33.00  27.00   0.50    2.00    --    0.00 -82.00 -60.00  120
  7  ω      7.00  64.00   0.50    9.03    --   95.80 -61.00-120.00  114
  8  ω     82.00 127.00   0.50    9.03    --   95.80 -82.00 150.00   90
  9  ω      6.00 108.00   0.50    9.03    --   95.80 -30.00   0.00  204
 10  ω      9.00 126.00   0.50    9.03    --   95.80 -82.00 -30.00  234
 11  ω     13.00 112.00   0.50    9.03    --   95.80 -30.00 120.00  198
 12  ω     42.00 120.00   0.50    9.03    --   95.80 -82.00 120.00  156
 13  ω    117.00 185.00   0.50    9.03    --   95.80  30.00 -90.00  136
 14  ω     15.00  61.00   0.50    9.03    --   95.80 -61.00 -90.00   92
 15  ω     61.00 127.00   0.50    9.03    --   95.80 -82.00  60.00  132
 16  ω      6.00  94.00   0.50    9.03    --   95.80 -45.00   0.00  176
 17  ω     96.00 170.00   0.50    9.03    --   95.80  30.00 -30.00  148
 18  ω     68.00 108.00   0.50    9.03    --   95.80 -61.00 -90.00   80
 19  ω     59.00  97.00   0.50    9.03    --   95.80 -82.00-150.00   76
 20  ω     80.00 107.00   0.50    9.03    --   95.80 -45.00 120.00   54
 21  ω     94.00 127.00   0.50    9.03    --   95.80 -82.00  30.00   66
 22  ω     54.00 120.00   0.50    9.03    --   95.80 -82.00 -73.07  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0912139000
_diffrn_orient_matrix_UB_12      -0.0214948000
_diffrn_orient_matrix_UB_13      -0.1118541000
_diffrn_orient_matrix_UB_21      0.0395462000
_diffrn_orient_matrix_UB_22      0.0862300000
_diffrn_orient_matrix_UB_23      -0.0238492000
_diffrn_orient_matrix_UB_31      0.2169637000
_diffrn_orient_matrix_UB_32      -0.0067538000
_diffrn_orient_matrix_UB_33      0.0513783000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2330
_reflns_number_total             2425
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.015
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 
;
 Flack x determined using 930 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0910
_refine_ls_restrained_S_all      1.127
_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)+(0.1739P)²+0.9992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2571
_refine_ls_wR_factor_ref         0.2585
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
O1: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O2 \\sim O1 \\sim O2A \\sim O1A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
3. Others
 Sof(O2A)=Sof(H2AA)=Sof(O1A)=1-FVAR(1)
 Sof(O2)=Sof(H2)=Sof(O1)=FVAR(1)
4.a Riding coordinates:
 O2(H2), O2A(H2AA)
4.b Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C2(H2A), C5(H5)
4.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C3(H3A,H3B), C10(H10A,H10B), C12(H12A,H12B)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C6(H6A,H6B,H6C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.4957(8) 0.4404(3) 0.1044(4) 0.0582(13) Uani 1 1 d . . . . .
C8 C 0.6556(8) 0.6092(3) 0.4124(5) 0.0386(12) Uani 1 1 d . . . . .
H8 H 0.785338 0.587962 0.445379 0.046 Uiso 1 1 calc R U . . .
C1 C 0.6552(8) 0.5848(3) 0.2914(4) 0.0342(11) Uani 1 1 d . . . . .
O2 O 0.3021(8) 0.6155(3) 0.4716(4) 0.0479(14) Uani 0.849(10) 1 d . U P A 1
H2 H 0.211323 0.594336 0.510514 0.072 Uiso 0.849(10) 1 d R U P A 1
O1 O 0.4897(9) 0.5157(3) 0.5271(5) 0.0542(16) Uani 0.849(10) 1 d . U P A 1
C9 C 0.6690(9) 0.6985(3) 0.4213(5) 0.0417(12) Uani 1 1 d . . . . .
H9A H 0.611224 0.714037 0.492708 0.050 Uiso 1 1 calc R U . . .
H9B H 0.817090 0.713364 0.420900 0.050 Uiso 1 1 calc R U . . .
C11 C 0.5765(7) 0.7094(3) 0.2176(4) 0.0338(11) Uani 1 1 d . . . . .
H11 H 0.500454 0.741168 0.162516 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5065(9) 0.4969(3) 0.1610(5) 0.0421(13) Uani 1 1 d . . . . .
C2 C 0.4796(8) 0.6279(3) 0.2286(4) 0.0347(11) Uani 1 1 d . . . . .
H2A H 0.354076 0.631117 0.276039 0.042 Uiso 1 1 calc R U . . .
C13 C 0.8038(8) 0.6952(3) 0.1820(5) 0.0358(12) Uani 1 1 d . . . . .
C3 C 0.4317(10) 0.5757(3) 0.1303(5) 0.0438(13) Uani 1 1 d . . . . .
H3A H 0.280955 0.574836 0.115426 0.053 Uiso 1 1 calc R U . . .
H3B H 0.504621 0.594491 0.064615 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5576(9) 0.7450(3) 0.3324(5) 0.0406(12) Uani 1 1 d . . . . .
H10A H 0.615437 0.798041 0.330867 0.049 Uiso 1 1 calc R U . . .
H10B H 0.409040 0.749100 0.351521 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4744(9) 0.5747(3) 0.4760(5) 0.0439(13) Uani 1 1 d . . . . .
C15 C 0.8273(10) 0.6919(4) 0.0585(5) 0.0474(14) Uani 1 1 d . . . . .
H15A H 0.739755 0.650407 0.029334 0.071 Uiso 1 1 calc R U . . .
H15B H 0.972331 0.681595 0.039868 0.071 Uiso 1 1 calc R U . . .
H15C H 0.784772 0.741434 0.026874 0.071 Uiso 1 1 calc R U . . .
C12 C 0.8539(7) 0.6146(3) 0.2350(4) 0.0356(12) Uani 1 1 d . . . . .
H12A H 0.899090 0.577471 0.178427 0.043 Uiso 1 1 calc R U . . .
H12B H 0.966909 0.620126 0.288948 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6113(9) 0.4991(3) 0.2713(5) 0.0426(13) Uani 1 1 d . . . . .
H5 H 0.498667 0.486017 0.324044 0.051 Uiso 1 1 calc R U . . .
C6 C 0.7742(11) 0.4409(4) 0.2923(6) 0.0520(16) Uani 1 1 d . . . . .
H6A H 0.905719 0.458855 0.261376 0.078 Uiso 1 1 calc R U . . .
H6B H 0.735106 0.391714 0.258376 0.078 Uiso 1 1 calc R U . . .
H6C H 0.789909 0.433587 0.370908 0.078 Uiso 1 1 calc R U . . .
C14 C 0.9538(9) 0.7597(4) 0.2171(5) 0.0463(14) Uani 1 1 d . . . . .
H14A H 0.907030 0.809187 0.186935 0.069 Uiso 1 1 calc R U . . .
H14B H 1.093118 0.748047 0.189976 0.069 Uiso 1 1 calc R U . . .
H14C H 0.956681 0.762921 0.296687 0.069 Uiso 1 1 calc R U . . .
O2A O 0.301(5) 0.549(2) 0.424(3) 0.064(7) Uani 0.151(10) 1 d . U P A 2
H2AA H 0.222996 0.526300 0.468527 0.095 Uiso 0.151(10) 1 d R U P A 2
O1A O 0.493(5) 0.574(2) 0.569(3) 0.060(7) Uani 0.151(10) 1 d . U P A 2


_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 C4 1.202(7) . ?
C8 H8 1.0000 . ?
C8 C1 1.546(8) . ?
C8 C9 1.549(8) . ?
C8 C7 1.527(8) . ?
C1 C2 1.560(7) . ?
C1 C12 1.546(7) . ?
C1 C5 1.528(8) . ?
O2 H2 0.8399 . ?
O2 C7 1.318(8) . ?
O1 C7 1.202(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.536(8) . ?
C11 H11 1.0000 . ?
C11 C2 1.548(7) . ?
C11 C13 1.551(7) . ?
C11 C10 1.544(8) . ?
C4 C3 1.492(8) . ?
C4 C5 1.515(9) . ?
C2 H2A 1.0000 . ?
C2 C3 1.539(7) . ?
C13 C15 1.526(8) . ?
C13 C12 1.571(8) . ?
C13 C14 1.539(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C7 O2A 1.37(4) . ?
C7 O1A 1.15(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C5 H5 1.0000 . ?
C5 C6 1.478(8) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O2A H2AA 0.8399 . ?

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
C1 C8 H8 106.9 . . ?
C1 C8 C9 109.9(5) . . ?
C9 C8 H8 106.9 . . ?
C7 C8 H8 106.9 . . ?
C7 C8 C1 112.6(5) . . ?
C7 C8 C9 113.3(5) . . ?
C8 C1 C2 110.3(4) . . ?
C8 C1 C12 109.8(4) . . ?
C12 C1 C2 102.8(4) . . ?
C5 C1 C8 114.9(4) . . ?
C5 C1 C2 104.3(4) . . ?
C5 C1 C12 113.8(5) . . ?
C7 O2 H2 109.4 . . ?
C8 C9 H9A 108.2 . . ?
C8 C9 H9B 108.2 . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 C8 116.4(5) . . ?
C10 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
C2 C11 H11 111.1 . . ?
C2 C11 C13 105.2(4) . . ?
C13 C11 H11 111.1 . . ?
C10 C11 H11 111.1 . . ?
C10 C11 C2 104.5(4) . . ?
C10 C11 C13 113.3(4) . . ?
O3 C4 C3 125.2(6) . . ?
O3 C4 C5 124.3(6) . . ?
C3 C4 C5 110.3(5) . . ?
C1 C2 H2A 109.1 . . ?
C11 C2 C1 100.6(4) . . ?
C11 C2 H2A 109.1 . . ?
C3 C2 C1 104.8(4) . . ?
C3 C2 C11 123.1(5) . . ?
C3 C2 H2A 109.1 . . ?
C11 C13 C12 102.6(4) . . ?
C15 C13 C11 112.4(5) . . ?
C15 C13 C12 111.0(5) . . ?
C15 C13 C14 104.1(5) . . ?
C14 C13 C11 113.6(5) . . ?
C14 C13 C12 113.4(4) . . ?
C4 C3 C2 105.8(4) . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C9 C10 C11 113.9(4) . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
O2 C7 C8 114.6(5) . . ?
O1 C7 C8 122.4(6) . . ?
O1 C7 O2 123.0(6) . . ?
O2A C7 C8 121.0(16) . . ?
O1A C7 C8 115.9(17) . . ?
O1A C7 O2A 123(2) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C12 C13 108.1(4) . . ?
C1 C12 H12A 110.1 . . ?
C1 C12 H12B 110.1 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
C1 C5 H5 104.5 . . ?
C4 C5 C1 104.6(4) . . ?
C4 C5 H5 104.5 . . ?
C6 C5 C1 120.0(5) . . ?
C6 C5 C4 117.2(5) . . ?
C6 C5 H5 104.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 O2A H2AA 109.7 . . ?

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
O3 C4 C3 C2 -179.9(6) . . . . ?
O3 C4 C5 C1 160.0(6) . . . . ?
O3 C4 C5 C6 24.4(9) . . . . ?
C8 C1 C2 C11 75.6(5) . . . . ?
C8 C1 C2 C3 -155.7(4) . . . . ?
C8 C1 C12 C13 -93.4(5) . . . . ?
C8 C1 C5 C4 150.2(4) . . . . ?
C8 C1 C5 C6 -75.8(7) . . . . ?
C8 C9 C10 C11 -38.9(7) . . . . ?
C1 C8 C9 C10 34.5(6) . . . . ?
C1 C8 C7 O2 -86.2(6) . . . . ?
C1 C8 C7 O1 94.8(7) . . . . ?
C1 C8 C7 O2A -21(2) . . . . ?
C1 C8 C7 O1A 161(2) . . . . ?
C1 C2 C3 C4 21.8(6) . . . . ?
C9 C8 C1 C2 -54.1(5) . . . . ?
C9 C8 C1 C12 58.6(5) . . . . ?
C9 C8 C1 C5 -171.6(4) . . . . ?
C9 C8 C7 O2 39.2(7) . . . . ?
C9 C8 C7 O1 -139.8(6) . . . . ?
C9 C8 C7 O2A 104.9(19) . . . . ?
C9 C8 C7 O1A -74(2) . . . . ?
C11 C2 C3 C4 135.3(5) . . . . ?
C11 C13 C12 C1 3.1(5) . . . . ?
C2 C1 C12 C13 24.0(5) . . . . ?
C2 C1 C5 C4 29.4(6) . . . . ?
C2 C1 C5 C6 163.4(5) . . . . ?
C2 C11 C13 C15 89.6(5) . . . . ?
C2 C11 C13 C12 -29.8(5) . . . . ?
C2 C11 C13 C14 -152.6(5) . . . . ?
C2 C11 C10 C9 59.3(5) . . . . ?
C13 C11 C2 C1 44.9(5) . . . . ?
C13 C11 C2 C3 -70.7(6) . . . . ?
C13 C11 C10 C9 -54.7(6) . . . . ?
C3 C4 C5 C1 -16.4(6) . . . . ?
C3 C4 C5 C6 -152.0(5) . . . . ?
C10 C11 C2 C1 -74.7(5) . . . . ?
C10 C11 C2 C3 169.7(5) . . . . ?
C10 C11 C13 C15 -156.8(5) . . . . ?
C10 C11 C13 C12 83.8(5) . . . . ?
C10 C11 C13 C14 -39.0(6) . . . . ?
C7 C8 C1 C2 73.2(6) . . . . ?
C7 C8 C1 C12 -174.2(4) . . . . ?
C7 C8 C1 C5 -44.3(6) . . . . ?
C7 C8 C9 C10 -92.4(6) . . . . ?
C15 C13 C12 C1 -117.1(5) . . . . ?
C12 C1 C2 C11 -41.4(5) . . . . ?
C12 C1 C2 C3 87.2(5) . . . . ?
C12 C1 C5 C4 -81.9(5) . . . . ?
C12 C1 C5 C6 52.0(7) . . . . ?
C5 C1 C2 C11 -160.5(4) . . . . ?
C5 C1 C2 C3 -31.9(5) . . . . ?
C5 C1 C12 C13 136.3(5) . . . . ?
C5 C4 C3 C2 -3.6(6) . . . . ?
C14 C13 C12 C1 126.1(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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.709

# start Validation Reply Form
_vrf_PLAT097_songyongxiang_xs-terb_collect 
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.01 eA-3  
RESPONSE: may be the crystal is not so clear.
;
# end Validation Reply Form
