#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:53:11 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/16/7241615.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_7241615
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, C7 H7 O, H2 O'
_chemical_formula_sum            'C17 H16 O5 S'
_chemical_formula_weight         332.36
_chemical_name_systematic        tropone
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-09-04
_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                 98.666(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7177(11)
_cell_length_b                   16.233(3)
_cell_length_c                   14.530(3)
_cell_measurement_reflns_used    2271
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.494
_cell_measurement_theta_min      2.510
_cell_volume                     1566.4(5)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0805
_diffrn_reflns_av_unetI/netI     0.1049
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6222
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_min         1.893
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 18039 reflections, Rint = 0.0730
 (7203 with I > 3sig(I), Rint = 0.0566)
;
_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    1.409
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3216
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0688
_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/[σ²(Fo²)+(0.0335P)²+1.9247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1490
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2025
_reflns_number_total             3216
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01551b2.cif
_cod_data_source_block           mo_22020146_0m_4
_cod_depositor_comments
'Adding full bibliography for 7241604--7241616.cif.'
_cod_database_code               7241615
_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   0.977
_shelx_estimated_absorpt_t_min   0.955
_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. Uiso/Uaniso restraints and constraints
Uanis(O4A) \\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(O4A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3. Others
 Fixed Sof: O3(0.88) O4(0.88) O2(0.88) O4A(0.12) O2A(0.12) O3A(0.12)
4.a Free rotating group:
 O5(H5A,H5B)
4.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C2(H2), C13(H13), C14(H14), C16(H16), C15(H15),
 C3(H3), C7(H7), C4(H4), C6(H6), C5(H5)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.75679(13) 0.45847(5) 0.81071(6) 0.0311(2) Uani 1 1 d . . . . .
O1 O 0.2426(4) 0.70044(16) 0.70862(15) 0.0414(6) Uani 1 1 d . . . . .
H1 H 0.2281 0.6494 0.7143 0.062 Uiso 1 1 calc GR . . . .
O5 O 0.2312(4) 0.54837(18) 0.73730(19) 0.0512(7) Uani 1 1 d . . . . .
H5A H 0.3441 0.5302 0.7659 0.077 Uiso 1 1 d G . . . .
H5B H 0.1346 0.5307 0.7647 0.077 Uiso 1 1 d G . . . .
O3 O 0.9313(5) 0.51222(19) 0.8355(2) 0.0472(8) Uani 0.88 1 d . . P A 1
O4 O 0.7312(5) 0.42727(18) 0.71869(17) 0.0454(8) Uani 0.88 1 d . . P A 1
O2 O 0.5750(5) 0.49853(19) 0.8366(2) 0.0502(8) Uani 0.88 1 d . . P A 1
C8 C 0.7749(4) 0.2956(2) 0.8538(2) 0.0280(7) Uani 1 1 d . . . . .
H8 H 0.7429 0.2869 0.7886 0.034 Uiso 1 1 calc R . . . .
C9 C 0.7961(4) 0.3732(2) 0.8874(2) 0.0264(7) Uani 1 1 d . . . . .
C10 C 0.8454(5) 0.3883(2) 0.9844(2) 0.0288(7) Uani 1 1 d . . . . .
H10 H 0.8603 0.4433 1.0069 0.035 Uiso 1 1 calc R . . . .
C11 C 0.8713(5) 0.3238(2) 1.0452(2) 0.0305(8) Uani 1 1 d . . . . .
H11 H 0.9052 0.3340 1.1101 0.037 Uiso 1 1 calc R . . . .
C17 C 0.8002(4) 0.2258(2) 0.9157(2) 0.0269(7) Uani 1 1 d . . . . .
C12 C 0.8480(4) 0.2418(2) 1.0123(2) 0.0270(7) Uani 1 1 d . . . . .
C2 C 0.1798(5) 0.6579(2) 0.5521(2) 0.0306(8) Uani 1 1 d . . . . .
H2 H 0.1947 0.6031 0.5750 0.037 Uiso 1 1 calc R . . . .
C13 C 0.8725(5) 0.1733(2) 1.0753(2) 0.0340(8) Uani 1 1 d . . . . .
H13 H 0.9044 0.1827 1.1404 0.041 Uiso 1 1 calc R . . . .
C1 C 0.2068(5) 0.7204(2) 0.6203(2) 0.0299(8) Uani 1 1 d . . . . .
C14 C 0.8501(5) 0.0944(2) 1.0419(3) 0.0371(9) Uani 1 1 d . . . . .
H14 H 0.8648 0.0492 1.0840 0.045 Uiso 1 1 calc R . . . .
C16 C 0.7815(5) 0.1444(2) 0.8836(2) 0.0336(8) Uani 1 1 d . . . . .
H16 H 0.7522 0.1338 0.8187 0.040 Uiso 1 1 calc R . . . .
C15 C 0.8051(5) 0.0799(2) 0.9451(3) 0.0369(8) Uani 1 1 d . . . . .
H15 H 0.7911 0.0250 0.9224 0.044 Uiso 1 1 calc R . . . .
C3 C 0.1349(5) 0.6657(2) 0.4573(2) 0.0366(8) Uani 1 1 d . . . . .
H3 H 0.1242 0.6151 0.4240 0.044 Uiso 1 1 calc R . . . .
C7 C 0.2008(5) 0.8068(2) 0.6035(3) 0.0365(9) Uani 1 1 d . . . . .
H7 H 0.2278 0.8408 0.6572 0.044 Uiso 1 1 calc R . . . .
C4 C 0.1026(5) 0.7359(3) 0.4020(3) 0.0434(10) Uani 1 1 d . . . . .
H4 H 0.0667 0.7266 0.3370 0.052 Uiso 1 1 calc R . . . .
C6 C 0.1612(5) 0.8474(2) 0.5204(3) 0.0466(10) Uani 1 1 d . . . . .
H6 H 0.1648 0.9057 0.5247 0.056 Uiso 1 1 calc R . . . .
C5 C 0.1158(5) 0.8158(3) 0.4291(3) 0.0474(11) Uani 1 1 d . . . . .
H5 H 0.0915 0.8556 0.3807 0.057 Uiso 1 1 calc R . . . .
O4A O 0.914(3) 0.4425(11) 0.7366(11) 0.025(4) Uani 0.12 1 d . U P A 2
O2A O 0.561(3) 0.4505(12) 0.7510(13) 0.030(4) Uani 0.12 1 d . U P A 2
O3A O 0.802(4) 0.5245(14) 0.8602(17) 0.051(6) Uani 0.12 1 d . U P A 2
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
O3 S1 O2 109.65(19) . . ?
O3 S1 C9 105.87(16) . . ?
O4 S1 O3 115.15(19) . . ?
O4 S1 O2 114.18(19) . . ?
O4 S1 C9 107.46(16) . . ?
O2 S1 C9 103.50(16) . . ?
O4A S1 C9 103.9(6) . . ?
O2A S1 C9 109.8(7) . . ?
O2A S1 O4A 102.0(10) . . ?
O3A S1 C9 107.2(11) . . ?
O3A S1 O4A 111.9(14) . . ?
O3A S1 O2A 120.8(14) . . ?
C1 O1 H1 109.5 . . ?
H5A O5 H5B 109.5 . . ?
C9 C8 H8 119.6 . . ?
C9 C8 C17 120.8(3) . . ?
C17 C8 H8 119.6 . . ?
C8 C9 S1 120.3(2) . . ?
C8 C9 C10 121.0(3) . . ?
C10 C9 S1 118.7(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C12 C17 C8 117.5(3) . . ?
C16 C17 C8 122.5(3) . . ?
C16 C17 C12 120.0(3) . . ?
C11 C12 C17 120.4(3) . . ?
C11 C12 C13 121.2(3) . . ?
C17 C12 C13 118.5(3) . . ?
C1 C2 H2 115.6 . . ?
C3 C2 H2 115.6 . . ?
C3 C2 C1 128.7(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
O1 C1 C2 119.7(3) . . ?
O1 C1 C7 114.0(3) . . ?
C2 C1 C7 126.2(3) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C17 C16 H16 119.7 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C2 C3 H3 114.9 . . ?
C2 C3 C4 130.3(4) . . ?
C4 C3 H3 114.9 . . ?
C1 C7 H7 115.7 . . ?
C6 C7 C1 128.5(4) . . ?
C6 C7 H7 115.7 . . ?
C3 C4 H4 115.9 . . ?
C5 C4 C3 128.2(4) . . ?
C5 C4 H4 115.9 . . ?
C7 C6 H6 115.0 . . ?
C7 C6 C5 130.0(4) . . ?
C5 C6 H6 115.0 . . ?
C4 C5 C6 128.0(4) . . ?
C4 C5 H5 116.0 . . ?
C6 C5 H5 116.0 . . ?
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 O3 1.462(3) . ?
S1 O4 1.416(3) . ?
S1 O2 1.481(3) . ?
S1 C9 1.772(3) . ?
S1 O4A 1.639(17) . ?
S1 O2A 1.468(17) . ?
S1 O3A 1.30(2) . ?
O1 H1 0.8400 . ?
O1 C1 1.310(4) . ?
O5 H5A 0.8600 . ?
O5 H5B 0.8603 . ?
C8 H8 0.9500 . ?
C8 C9 1.351(4) . ?
C8 C17 1.441(4) . ?
C9 C10 1.420(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.364(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.415(5) . ?
C17 C12 1.416(4) . ?
C17 C16 1.401(5) . ?
C12 C13 1.434(5) . ?
C2 H2 0.9500 . ?
C2 C1 1.410(4) . ?
C2 C3 1.372(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.371(5) . ?
C1 C7 1.424(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.414(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.369(5) . ?
C15 H15 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.393(5) . ?
C7 H7 0.9500 . ?
C7 C6 1.366(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.355(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.411(6) . ?
C5 H5 0.9500 . ?
