#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/16/7241605.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7241605
loop_
_publ_author_name
'Ma, Xiaoyu'
'Zhu, Bingqing'
'Yang, Zeen'
'Jiang, Yuhang'
'Mei, Xuefeng'
_publ_section_title
;
 Stabilizing photo-sensitive colchicine through rebalancing electron
 distribution of the reactive tropolone ring
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              30
_journal_page_last               34
_journal_paper_doi               10.1039/D0CE01551B
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C10 H7 O3 S, C10 H13 O2, H2 O'
_chemical_formula_sum            'C20 H22 O6 S'
_chemical_formula_weight         390.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-11-13 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.052(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2402(4)
_cell_length_b                   31.6946(17)
_cell_length_c                   6.4645(3)
_cell_measurement_reflns_used    4540
_cell_measurement_temperature    180
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.34
_cell_volume                     1858.11(15)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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)'
_diffrn_ambient_temperature      180.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11234
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.336
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0875 before and 0.0497 after correction. The Ratio of minimum to maximum transmission is 0.9392. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3687
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0345
_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)+(0.0296P)²+0.4961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0713
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.814
_reflns_Friedel_fraction_max     0.729
_reflns_number_gt                3381
_reflns_number_total             3687
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01551b2.cif
_cod_data_source_block           22019951_0m
_cod_depositor_comments
'Adding full bibliography for 7241604--7241616.cif.'
_cod_database_code               7241605
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Ternary CH refined with riding coordinates:
 C8(H8)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C13(H13), C5(H5), C6(H6), C11(H11), C7(H7), C19(H19), C17(H17),
 C14(H14), C18(H18), C16(H16)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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
S1 S 0.67103(8) 0.39780(2) 0.54346(11) 0.02859(17) Uani 1 1 d . . . . .
O1 O 0.2757(2) 0.43422(6) 0.3840(3) 0.0249(4) Uani 1 1 d . . . . .
H1 H 0.3681 0.4323 0.4047 0.037 Uiso 1 1 calc GR . . . .
O2 O 0.48357(19) 0.48843(6) 0.4623(3) 0.0249(4) Uani 1 1 d . . . . .
H2 H 0.5466 0.5073 0.5024 0.037 Uiso 1 1 calc GR . . . .
O5 O 0.7589(2) 0.42981(6) 0.4654(3) 0.0362(5) Uani 1 1 d . . . . .
O6 O 0.6999(2) 0.53691(6) 0.5676(3) 0.0313(5) Uani 1 1 d . . . . .
H6A H 0.7126 0.5493 0.6897 0.047 Uiso 1 1 d G . . . .
H6B H 0.7021 0.5556 0.4697 0.047 Uiso 1 1 d G . . . .
O3 O 0.5253(2) 0.39341(6) 0.4107(4) 0.0392(5) Uani 1 1 d . . . . .
O4 O 0.6673(3) 0.40225(7) 0.7655(4) 0.0517(7) Uani 1 1 d . . . . .
C1 C 0.2368(3) 0.47462(8) 0.3727(4) 0.0206(6) Uani 1 1 d . . . . .
C2 C 0.3508(3) 0.50572(8) 0.4162(4) 0.0201(5) Uani 1 1 d . . . . .
C3 C 0.3340(3) 0.54950(8) 0.4187(4) 0.0206(5) Uani 1 1 d . . . . .
H3 H 0.4239 0.5647 0.4546 0.025 Uiso 1 1 calc R . . . .
C13 C 0.8256(3) 0.34286(9) 0.3407(5) 0.0310(6) Uani 1 1 d . . . . .
H13 H 0.8197 0.3643 0.2367 0.037 Uiso 1 1 calc R . . . .
C5 C 0.0642(3) 0.56074(9) 0.3136(4) 0.0261(6) Uani 1 1 d . . . . .
H5 H -0.0083 0.5823 0.2844 0.031 Uiso 1 1 calc R . . . .
C6 C 0.0111(3) 0.51995(9) 0.2860(4) 0.0265(6) Uani 1 1 d . . . . .
H6 H -0.0924 0.5175 0.2387 0.032 Uiso 1 1 calc R . . . .
C11 C 0.7702(3) 0.31897(9) 0.6716(5) 0.0267(6) Uani 1 1 d . . . . .
H11 H 0.7278 0.3240 0.7920 0.032 Uiso 1 1 calc R . . . .
C12 C 0.7624(3) 0.34924(8) 0.5200(4) 0.0248(6) Uani 1 1 d . . . . .
C7 C 0.0871(3) 0.48195(9) 0.3175(4) 0.0236(6) Uani 1 1 d . . . . .
H7 H 0.0271 0.4574 0.2982 0.028 Uiso 1 1 calc R . . . .
C20 C 0.8413(3) 0.27995(9) 0.6504(5) 0.0282(6) Uani 1 1 d . . . . .
C9 C 0.1283(3) 0.64282(10) 0.5287(5) 0.0364(7) Uani 1 1 d . . . . .
H9A H 0.0271 0.6397 0.4501 0.055 Uiso 1 1 calc GR . . . .
H9B H 0.1523 0.6729 0.5483 0.055 Uiso 1 1 calc GR . . . .
H9C H 0.1372 0.6292 0.6667 0.055 Uiso 1 1 calc GR . . . .
C8 C 0.2341(3) 0.62220(8) 0.4068(5) 0.0271(6) Uani 1 1 d . . . . .
H8 H 0.3365 0.6264 0.4887 0.032 Uiso 1 1 calc R . . . .
C4 C 0.2083(3) 0.57484(8) 0.3778(4) 0.0232(6) Uani 1 1 d . . . . .
C15 C 0.9047(3) 0.27347(9) 0.4699(5) 0.0292(6) Uani 1 1 d . . . . .
C19 C 0.8531(3) 0.24759(10) 0.8034(5) 0.0386(8) Uani 1 1 d . . . . .
H19 H 0.8097 0.2514 0.9239 0.046 Uiso 1 1 calc R . . . .
C17 C 0.9885(4) 0.20472(10) 0.6016(6) 0.0439(9) Uani 1 1 d . . . . .
H17 H 1.0390 0.1791 0.5871 0.053 Uiso 1 1 calc R . . . .
C14 C 0.8950(3) 0.30580(10) 0.3174(5) 0.0344(7) Uani 1 1 d . . . . .
H14 H 0.9377 0.3016 0.1965 0.041 Uiso 1 1 calc R . . . .
C18 C 0.9257(4) 0.21110(10) 0.7805(6) 0.0455(9) Uani 1 1 d . . . . .
H18 H 0.9340 0.1899 0.8858 0.055 Uiso 1 1 calc R . . . .
C10 C 0.2243(4) 0.64378(10) 0.1927(5) 0.0454(9) Uani 1 1 d . . . . .
H10A H 0.1264 0.6389 0.1062 0.068 Uiso 1 1 calc GR . . . .
H10B H 0.2998 0.6321 0.1213 0.068 Uiso 1 1 calc GR . . . .
H10C H 0.2403 0.6742 0.2137 0.068 Uiso 1 1 calc GR . . . .
C16 C 0.9782(3) 0.23461(10) 0.4493(6) 0.0403(8) Uani 1 1 d . . . . .
H16 H 1.0201 0.2296 0.3284 0.048 Uiso 1 1 calc R . . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O5 S1 O3 112.20(13) . . ?
O5 S1 C12 105.64(13) . . ?
O3 S1 C12 105.52(12) . . ?
O4 S1 O5 113.45(14) . . ?
O4 S1 O3 113.42(15) . . ?
O4 S1 C12 105.73(14) . . ?
C1 O1 H1 109.5 . . ?
C2 O2 H2 109.5 . . ?
H6A O6 H6B 109.5 . . ?
O1 C1 C2 118.2(2) . . ?
O1 C1 C7 115.1(2) . . ?
C7 C1 C2 126.8(2) . . ?
O2 C2 C1 112.0(2) . . ?
O2 C2 C3 120.6(2) . . ?
C3 C2 C1 127.4(2) . . ?
C2 C3 H3 114.3 . . ?
C4 C3 C2 131.3(2) . . ?
C4 C3 H3 114.3 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C6 C5 H5 115.3 . . ?
C6 C5 C4 129.4(3) . . ?
C4 C5 H5 115.3 . . ?
C5 C6 H6 115.3 . . ?
C5 C6 C7 129.4(3) . . ?
C7 C6 H6 115.3 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C20 120.4(3) . . ?
C20 C11 H11 119.8 . . ?
C13 C12 S1 118.3(2) . . ?
C11 C12 S1 120.6(2) . . ?
C11 C12 C13 121.2(3) . . ?
C1 C7 C6 129.6(3) . . ?
C1 C7 H7 115.2 . . ?
C6 C7 H7 115.2 . . ?
C15 C20 C11 118.5(3) . . ?
C19 C20 C11 122.7(3) . . ?
C19 C20 C15 118.8(3) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
C9 C8 H8 107.8 . . ?
C9 C8 C4 112.8(2) . . ?
C9 C8 C10 110.2(2) . . ?
C4 C8 H8 107.8 . . ?
C4 C8 C10 110.4(2) . . ?
C10 C8 H8 107.8 . . ?
C3 C4 C8 116.0(2) . . ?
C5 C4 C3 125.9(3) . . ?
C5 C4 C8 118.1(2) . . ?
C20 C15 C16 118.8(3) . . ?
C14 C15 C20 119.2(3) . . ?
C14 C15 C16 122.0(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 C20 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(3) . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
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
S1 O5 1.450(2) . ?
S1 O3 1.458(2) . ?
S1 O4 1.449(2) . ?
S1 C12 1.776(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.328(3) . ?
O2 H2 0.8400 . ?
O2 C2 1.325(3) . ?
O6 H6A 0.8701 . ?
O6 H6B 0.8701 . ?
C1 C2 1.430(4) . ?
C1 C7 1.381(4) . ?
C2 C3 1.397(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.409(4) . ?
C13 C14 1.360(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(4) . ?
C5 C4 1.390(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.363(4) . ?
C11 C20 1.419(4) . ?
C7 H7 0.9500 . ?
C20 C15 1.418(4) . ?
C20 C19 1.414(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C8 1.517(4) . ?
C8 H8 1.0000 . ?
C8 C4 1.526(4) . ?
C8 C10 1.530(4) . ?
C15 C14 1.413(4) . ?
C15 C16 1.425(4) . ?
C19 H19 0.9500 . ?
C19 C18 1.359(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.404(5) . ?
C17 C16 1.356(5) . ?
C14 H14 0.9500 . ?
C18 H18 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C16 H16 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168341777
