Stabilizing photo-sensitive colchicine through rebalancing electron distribution of the reactive tropolone ring
Ma, Xiaoyu; Zhu, Bingqing; Yang, Zeen; Jiang, Yuhang; Mei, Xuefeng; CrystEngComm 23 (2021) 30–34; doi:10.1039/D0CE01551B

data_7241607
_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         'C7 H7 O3 S, C22 H26 N O6'
_chemical_formula_sum            'C29 H33 N O9 S'
_chemical_formula_weight         571.62
_chemical_name_common            colchicine
_chemical_name_systematic        Colchicine-AII2
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-04 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.313(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.858(3)
_cell_length_b                   8.1256(19)
_cell_length_c                   13.356(3)
_cell_measurement_reflns_used    1349
_cell_measurement_temperature    220
_cell_measurement_theta_max      20.48
_cell_measurement_theta_min      2.22
_cell_volume                     1395.1(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      220
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.1240
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12708
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         1.525
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;SADABS;2012
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       needle
_exptl_crystal_F_000             604
_exptl_crystal_preparation       'MEK evaporation'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1144 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6298
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0542
_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/[\s^2^(Fo^2^)+(0.0368P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3621
_reflns_number_total             6298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01551b2.cif
_cod_data_source_block           colchicine-aii2
_cod_depositor_comments
'Adding full bibliography for 7241604--7241616.cif.'
_cod_database_code               7241607
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.919
_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. Restrained distances
 O4-H4
 0.83 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C6(H6a,H6b)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C24(H24), C23(H23), C11(H11), C4(H4a), C20(H20), C12(H12),
 C21(H21)
3.d Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C17(H17a,H17b,H17c), C15(H15a,H15b,H15c), C18(H18a,H18b,
 H18c), C13(H13a,H13b,H13c), C14(H14a,H14b,H14c)
;
_olex2_exptl_crystal_mounting_method ' '
_olex2_submission_original_sample_id Colchicne-AII2
_olex2_submission_special_instructions 'No special instructions were received'