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_7241616
_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, C7 H7 O2, 3(H2 O)'
_chemical_formula_sum            'C17 H20 O8 S'
_chemical_formula_weight         384.39
_chemical_name_systematic        tropolone
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_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                 102.749(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7888(4)
_cell_length_b                   20.0960(12)
_cell_length_c                   13.5491(8)
_cell_measurement_reflns_used    4765
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.354
_cell_measurement_theta_min      2.546
_cell_volume                     1802.90(19)
_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      170.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0638
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.378
_diffrn_reflns_theta_min         2.546
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0633 before and 0.0518 after correction. The Ratio of minimum to maximum transmission is 0.9112. The \l/2 correction factor is Not present.'
_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    1.416
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     509
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0317P)^2^+2.9544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1493
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2765
_reflns_number_total             3683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01551b2.cif
_cod_data_source_block           220191031_0m
_cod_depositor_comments
'Adding full bibliography for 7241604--7241616.cif.'
_cod_database_code               7241616
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 S1-C19 \\sim S1-C9
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Others
 Fixed Sof: C9(0.65) C8(0.65) H8A(0.65) C13(0.65) H13(0.65) C12(0.65)
 C10(0.65) H10(0.65) C16(0.65) H16(0.65) C15(0.65) H15(0.65) C11(0.65)
 H11(0.65) C27(0.35) C22(0.35) C23(0.35) H23(0.35) C24(0.35) H24(0.35)
 C25(0.35) H25(0.35) C26(0.35) H26(0.35) C18(0.35) H18(0.35) C19(0.35)
 C20(0.35) H20(0.35) C21(0.35) H21(0.35) C14(0.65) H14(0.65) C17(0.65)
6.a Free rotating group:
 O6(H6a,H6b), O7(H7a,H7b)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3), C5(H5), C4(H4), C8(H8A), C13(H13), C10(H10), C16(H16),
  C15(H15), C11(H11), C23(H23), C24(H24), C25(H25), C26(H26), C18(H18),
 C20(H20), C21(H21), C14(H14)
6.c Fitted hexagon refined as free rotating group:
 C27(C22,C23,C24,C25,C26)
6.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'