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_7241613
_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         'C22 H25 N O6, 1.5(H2 O)'
_chemical_formula_sum            'C22 H28 N O7.5'
_chemical_formula_weight         426.45
_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             2020-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-13 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.885(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.829(4)
_cell_length_b                   10.484(4)
_cell_length_c                   15.998(5)
_cell_measurement_reflns_used    1482
_cell_measurement_temperature    205
_cell_measurement_theta_max      19.966
_cell_measurement_theta_min      2.37
_cell_volume                     2167.0(12)
_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      205
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_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  0.0924
_diffrn_reflns_av_unetI/netI     0.1614
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19131
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.694
_diffrn_reflns_theta_min         1.576
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0896 before and 0.0676 after correction. The Ratio of minimum to maximum transmission is 0.7393. The \l/2 correction factor is 0.00150.'
_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    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             908
_exptl_crystal_preparation       H2O
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         9854
_refine_ls_number_restraints     451
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.1701
_refine_ls_R_factor_gt           0.0760
_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^)+(0.0840P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.2126
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                4603
_reflns_number_total             9854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01551b2.cif
_cod_data_source_block           mo_20180153_0m
_cod_depositor_comments
;
Adding full bibliography for 7241604--7241616.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2167.1(12)
_cod_original_formula_moiety     '2(C22 H25 N O6), 3(H2 O)'
_cod_original_formula_sum        'C44 H56 N2 O15'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     852.90
_cod_database_code               7241613
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.973
_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, All O(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Free rotating group:
 O7(H7A,H7B), O8(H8A,H8B), O9(H9A,H9B)
3.b Ternary CH refined with riding coordinates:
 C25(H25), C7(H7)
3.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C24(H24A,H24B), C23(H23A,H23B), C5(H5A,H5B)
3.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C11(H11), C22(H22), C8(H8), C29(H29), C12(H12), C30(H30),
 C26(H26), C4(H4)
3.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C18(H18A,H18B,
 H18C), C35(H35A,H35B,H35C), C32(H32A,H32B,H32C), C13(H13A,H13B,H13C), C15(H15A,
 H15B,H15C), C17(H17A,H17B,H17C), C31(H31A,H31B,H31C)
;
_olex2_submission_special_instructions 'No special instructions were received'