#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:53:11 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/16/7241609.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_7241609
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 H6 O6 S2, 2(C10 H13 O2)'
_chemical_formula_sum            'C30 H32 O10 S2'
_chemical_formula_weight         616.67
_chemical_name_systematic        hinokitiol
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_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                81.489(2)
_cell_angle_beta                 78.810(2)
_cell_angle_gamma                70.4640(10)
_cell_formula_units_Z            1
_cell_length_a                   6.8451(3)
_cell_length_b                   9.0199(4)
_cell_length_c                   12.2623(6)
_cell_measurement_reflns_used    4026
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.465
_cell_measurement_theta_min      2.405
_cell_volume                     697.12(6)
_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      150.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.874
_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  0.0324
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9256
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.573
_diffrn_reflns_theta_min         2.406
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0730 before and 0.0465 after correction.
The Ratio of minimum to maximum transmission is 0.9094.
The λ/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    1.469
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0507
_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)+(0.0447P)²+0.9330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2680
_reflns_number_total             3738
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01551b2.cif
_cod_data_source_block           22019968_0m
_cod_depositor_comments
'Adding full bibliography for 7241604--7241616.cif.'
_cod_database_code               7241609
_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   0.975
_shelx_estimated_absorpt_t_min   0.975
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C17(H17), C5(H5), C6(H6), C18(H18), C19(H19), C3(H3)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C9(H9a,H9b,H9c)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.45479(10) 0.48266(7) 0.72784(5) 0.02404(16) Uani 1 1 d . . . . .
O5 O 0.3263(3) 0.3787(2) 0.75412(14) 0.0316(4) Uani 1 1 d . . . . .
O3 O 0.6316(3) 0.42840(19) 0.63820(13) 0.0278(4) Uani 1 1 d . . . . .
O2 O 0.7611(3) 0.6178(2) 0.48472(14) 0.0299(4) Uani 1 1 d . . . . .
H2 H 0.7179 0.5642 0.5403 0.045 Uiso 1 1 calc GR . . . .
O4 O 0.3377(3) 0.6472(2) 0.70813(15) 0.0327(4) Uani 1 1 d . . . . .
O1 O 0.7812(3) 0.8295(2) 0.32278(14) 0.0287(4) Uani 1 1 d . . . . .
H1 H 0.7535 0.7446 0.3270 0.043 Uiso 1 1 calc GR . . . .
C7 C 0.7559(4) 1.0227(3) 0.4310(2) 0.0238(5) Uani 1 1 d . . . . .
H7 H 0.7619 1.0842 0.3612 0.029 Uiso 1 1 calc R . . . .
C20 C 0.5525(4) 0.4896(2) 1.04704(18) 0.0197(4) Uani 1 1 d . . . . .
C16 C 0.5737(4) 0.4617(3) 0.84883(18) 0.0209(4) Uani 1 1 d . . . . .
C1 C 0.7693(3) 0.8680(3) 0.42510(19) 0.0228(5) Uani 1 1 d . . . . .
C17 C 0.7865(4) 0.3971(3) 0.8393(2) 0.0249(5) Uani 1 1 d . . . . .
H17 H 0.8670 0.3653 0.7696 0.030 Uiso 1 1 calc R . . . .
C5 C 0.7342(4) 1.0451(3) 0.6352(2) 0.0249(5) Uani 1 1 d . . . . .
H5 H 0.7164 1.1211 0.6854 0.030 Uiso 1 1 calc R . . . .
C6 C 0.7350(4) 1.1021(3) 0.5237(2) 0.0241(5) Uani 1 1 d . . . . .
H6 H 0.7188 1.2116 0.5084 0.029 Uiso 1 1 calc R . . . .
C2 C 0.7656(4) 0.7509(3) 0.5167(2) 0.0240(5) Uani 1 1 d . . . . .
C4 C 0.7560(4) 0.8919(3) 0.68389(19) 0.0235(5) Uani 1 1 d . . . . .
C18 C 0.8872(4) 0.3775(3) 0.9330(2) 0.0268(5) Uani 1 1 d . . . . .
H18 H 1.0354 0.3329 0.9259 0.032 Uiso 1 1 calc R . . . .
C19 C 0.7733(4) 0.4221(3) 1.03356(19) 0.0242(5) Uani 1 1 d . . . . .
H19 H 0.8435 0.4077 1.0958 0.029 Uiso 1 1 calc R . . . .
C3 C 0.7697(4) 0.7640(3) 0.6276(2) 0.0249(5) Uani 1 1 d . . . . .
H3 H 0.7847 0.6679 0.6740 0.030 Uiso 1 1 calc R . . . .
C8 C 0.7496(4) 0.8598(3) 0.8097(2) 0.0284(5) Uani 1 1 d . . . . .
H8 H 0.8225 0.7446 0.8261 0.034 Uiso 1 1 calc R . . . .
C10 C 0.5206(5) 0.8942(4) 0.8659(2) 0.0375(6) Uani 1 1 d . . . . .
H10A H 0.4460 1.0073 0.8537 0.056 Uiso 1 1 calc GR . . . .
H10B H 0.5156 0.8632 0.9461 0.056 Uiso 1 1 calc GR . . . .
H10C H 0.4537 0.8340 0.8336 0.056 Uiso 1 1 calc GR . . . .
C9 C 0.8595(5) 0.9505(3) 0.8589(2) 0.0367(6) Uani 1 1 d . . . . .
H9A H 1.0041 0.9296 0.8201 0.055 Uiso 1 1 calc GR . . . .
H9B H 0.8606 0.9162 0.9385 0.055 Uiso 1 1 calc GR . . . .
H9C H 0.7844 1.0640 0.8496 0.055 Uiso 1 1 calc GR . . . .
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 112.09(10) . . ?
O5 S1 C16 105.16(10) . . ?
O3 S1 C16 104.70(11) . . ?
O4 S1 O5 114.09(12) . . ?
O4 S1 O3 112.45(11) . . ?
O4 S1 C16 107.50(10) . . ?
C2 O2 H2 109.5 . . ?
C1 O1 H1 109.5 . . ?
C1 C7 H7 115.1 . . ?
C1 C7 C6 129.7(2) . . ?
C6 C7 H7 115.1 . . ?
C20 C20 C16 117.7(3) 2_667 2_667 ?
C19 C20 C20 119.1(3) . 2_667 ?
C19 C20 C16 123.2(2) . 2_667 ?
C20 C16 S1 120.46(17) 2_667 . ?
C17 C16 S1 118.16(17) . . ?
C17 C16 C20 121.4(2) . 2_667 ?
O1 C1 C7 114.9(2) . . ?
O1 C1 C2 118.6(2) . . ?
C7 C1 C2 126.5(2) . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C6 C5 H5 115.5 . . ?
C6 C5 C4 129.0(2) . . ?
C4 C5 H5 115.5 . . ?
C7 C6 H6 115.2 . . ?
C5 C6 C7 129.5(2) . . ?
C5 C6 H6 115.2 . . ?
O2 C2 C1 111.9(2) . . ?
O2 C2 C3 120.9(2) . . ?
C3 C2 C1 127.2(2) . . ?
C5 C4 C3 125.3(2) . . ?
C5 C4 C8 118.7(2) . . ?
C3 C4 C8 115.8(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C20 C19 H19 119.4 . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19 119.4 . . ?
C2 C3 C4 132.1(2) . . ?
C2 C3 H3 113.9 . . ?
C4 C3 H3 113.9 . . ?
C4 C8 H8 107.5 . . ?
C4 C8 C10 108.9(2) . . ?
C4 C8 C9 114.3(2) . . ?
C10 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C9 C8 C10 110.9(2) . . ?
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 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
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 1.4517(18) . ?
S1 O3 1.4693(18) . ?
S1 O4 1.4409(18) . ?
S1 C16 1.784(2) . ?
O2 H2 0.8400 . ?
O2 C2 1.328(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.331(3) . ?
C7 H7 0.9500 . ?
C7 C1 1.379(3) . ?
C7 C6 1.391(3) . ?
C20 C20 1.432(4) 2_667 ?
C20 C16 1.433(3) 2_667 ?
C20 C19 1.414(3) . ?
C16 C20 1.433(3) 2_667 ?
C16 C17 1.364(3) . ?
C1 C2 1.426(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.411(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C5 C4 1.393(3) . ?
C6 H6 0.9500 . ?
C2 C3 1.388(3) . ?
C4 C3 1.398(3) . ?
C4 C8 1.522(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.362(3) . ?
C19 H19 0.9500 . ?
C3 H3 0.9500 . ?
C8 H8 1.0000 . ?
C8 C10 1.532(4) . ?
C8 C9 1.527(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
