#------------------------------------------------------------------------------
#$Date: 2022-03-31 04:01:52 +0300 (Thu, 31 Mar 2022) $
#$Revision: 274154 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158615.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_7158615
loop_
_publ_author_name
'Nakagawa, Yuma'
'Hishida, Tatsuya'
'Hatano, Eri'
'Sumaru, Kimio'
'Morishita, Kana'
'Morimoto, Masakazu'
'Yokojima, Satoshi'
'Nakamura, Shinichiro'
'Uchida, Kingo'
_publ_section_title
;
 Photoinduced cytotoxicity of photochromic symmetric diarylethene
 derivatives: the relation of structure and cytotoxicity
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00224H
_journal_year                    2022
_chemical_formula_sum            'C33 H32 F6 N2 S2'
_chemical_formula_weight         634.72
_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   geom
_audit_block_doi                 10.5517/ccdc.csd.cc28b53x
_audit_update_record
;
2021-07-07 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.3338(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9900(5)
_cell_length_b                   21.3155(10)
_cell_length_c                   12.2134(5)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      24.9765
_cell_measurement_theta_min      2.5382
_cell_volume                     3116.1(2)
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            122967
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.078
_refine_diff_density_min         -0.544
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0554
_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)+(0.0846P)²+4.0631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1576
_reflns_number_gt                4684
_reflns_number_total             5505
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00224h2.cif
_cod_data_source_block           uch101_thiamtbu
_cod_database_code               7158615
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5403(3) 0.38033(16) 1.0650(2) 0.0433(7) Uani d . . . 1 . .
H H1A 0.5106 0.3376 1.0691 0.065 Uiso calc U . R 1 . .
H H1B 0.5034 0.4073 1.1169 0.065 Uiso calc U . R 1 . .
H H1C 0.6209 0.3798 1.0836 0.065 Uiso calc U . R 1 . .
C C2 0.5188(2) 0.40521(12) 0.9511(2) 0.0312(6) Uani d . . . 1 . .
C C3 0.5889(2) 0.40989(11) 0.8677(2) 0.0260(5) Uani d . . . 1 . .
C C4 0.4411(2) 0.45294(12) 0.7810(2) 0.0276(5) Uani d . . . 1 . .
C C5 0.3686(2) 0.48141(11) 0.6930(2) 0.0274(5) Uani d . . . 1 . .
C C6 0.3965(2) 0.47516(12) 0.5843(2) 0.0322(6) Uani d . . . 1 . .
H H6 0.4621 0.4531 0.5672 0.039 Uiso calc U . R 1 . .
C C7 0.3277(2) 0.50132(14) 0.5017(2) 0.0363(6) Uani d . . . 1 . .
H H7 0.3466 0.4974 0.4275 0.044 Uiso calc U . R 1 . .
C C8 0.2313(2) 0.53328(13) 0.5260(2) 0.0339(6) Uani d . . . 1 . .
H H8 0.1848 0.5506 0.4681 0.041 Uiso calc U . R 1 . .
C C9 0.2018(2) 0.54028(12) 0.6333(2) 0.0303(6) Uani d . . . 1 . .
C C10 0.2723(2) 0.51390(12) 0.7162(2) 0.0300(6) Uani d . . . 1 . .
H H10 0.2539 0.5183 0.7904 0.036 Uiso calc U . R 1 . .
C C11 0.0996(2) 0.57846(14) 0.6630(2) 0.0375(7) Uani d . . . 1 . .
C C12 0.1434(3) 0.63907(17) 0.7183(4) 0.0654(10) Uani d . . . 1 . .
H H12A 0.0802 0.6654 0.7367 0.098 Uiso calc U . R 1 . .
H H12B 0.1896 0.6619 0.668 0.098 Uiso calc U . R 1 . .
H H12C 0.1884 0.6286 0.7854 0.098 Uiso calc U . R 1 . .
C C13 0.0264(3) 0.5979(2) 0.5622(3) 0.0777(13) Uani d . . . 1 . .
H H13A 0.0013 0.5604 0.5215 0.117 Uiso calc U . R 1 . .
H H13B 0.0696 0.6246 0.515 0.117 Uiso calc U . R 1 . .
H H13C -0.0387 0.6211 0.5855 0.117 Uiso calc U . R 1 . .
C C14 0.0310(3) 0.5422(2) 0.7395(4) 0.0757(13) Uani d . . . 1 . .
H H14A 0.0042 0.5035 0.7035 0.114 Uiso calc U . R 1 . .
H H14B -0.033 0.5676 0.759 0.114 Uiso calc U . R 1 . .
H H14C 0.0768 0.5317 0.806 0.114 Uiso calc U . R 1 . .
C C15 0.7695(3) 0.22807(16) 1.1090(2) 0.0448(8) Uani d . . . 1 . .
H H15A 0.8331 0.2013 1.093 0.067 Uiso calc U . R 1 . .
H H15B 0.7303 0.2099 1.1697 0.067 Uiso calc U . R 1 . .
H H15C 0.7965 0.2701 1.1296 0.067 Uiso calc U . R 1 . .
C C16 0.6907(2) 0.23249(12) 1.0090(2) 0.0301(6) Uani d . . . 1 . .
C C17 0.6790(2) 0.27651(11) 0.9277(2) 0.0246(5) Uani d . . . 1 . .
C C18 0.5367(2) 0.21569(12) 0.8719(2) 0.0267(5) Uani d . . . 1 . .
C C19 0.4382(2) 0.19316(12) 0.8062(2) 0.0277(5) Uani d . . . 1 . .
C C20 0.3805(2) 0.23480(12) 0.7355(2) 0.0277(5) Uani d . . . 1 . .
H H20 0.4072 0.2766 0.7295 0.033 Uiso calc U . R 1 . .
C C21 0.2852(2) 0.21685(13) 0.6737(2) 0.0314(6) Uani d . . . 1 . .
C C22 0.2495(3) 0.15449(15) 0.6844(2) 0.0428(7) Uani d . . . 1 . .
H H22 0.1849 0.1406 0.6426 0.051 Uiso calc U . R 1 . .
C C23 0.3058(3) 0.11319(15) 0.7539(3) 0.0477(8) Uani d . . . 1 . .
H H23 0.2795 0.0713 0.7596 0.057 Uiso calc U . R 1 . .
C C24 0.4007(3) 0.13188(13) 0.8157(2) 0.0389(7) Uani d . . . 1 . .
H H24 0.4394 0.1032 0.8639 0.047 Uiso calc U . R 1 . .
C C25 0.2178(2) 0.26200(14) 0.5988(2) 0.0361(6) Uani d . . . 1 . .
C C26 0.2081(3) 0.23582(19) 0.4817(3) 0.0581(9) Uani d . . . 1 . .
H H26A 0.1637 0.2646 0.4342 0.087 Uiso calc U . R 1 . .
H H26B 0.1715 0.1947 0.4818 0.087 Uiso calc U . R 1 . .
H H26C 0.2828 0.2314 0.4541 0.087 Uiso calc U . R 1 . .
C C27 0.2708(3) 0.32695(16) 0.5954(3) 0.0521(9) Uani d . . . 1 . .
H H27A 0.2752 0.3451 0.6692 0.078 Uiso calc U . R 1 . .
H H27B 0.2252 0.354 0.5458 0.078 Uiso calc U . R 1 . .
H H27C 0.3462 0.3234 0.5689 0.078 Uiso calc U . R 1 . .
C C28 0.1007(3) 0.26847(18) 0.6415(3) 0.0526(8) Uani d . . . 1 . .
H H28A 0.1065 0.285 0.7165 0.079 Uiso calc U . R 1 . .
H H28B 0.0644 0.2273 0.6412 0.079 Uiso calc U . R 1 . .
H H28C 0.0562 0.2973 0.5941 0.079 Uiso calc U . R 1 . .
C C29 0.7062(2) 0.38909(12) 0.8760(2) 0.0253(5) Uani d . . . 1 . .
C C30 0.7995(2) 0.43303(12) 0.8523(2) 0.0309(6) Uani d . . . 1 . .
C C31 0.9057(2) 0.39323(13) 0.8625(2) 0.0362(6) Uani d . . . 1 . .
C C32 0.8713(2) 0.33352(12) 0.9214(2) 0.0313(6) Uani d . . . 1 . .
C C33 0.7458(2) 0.33310(11) 0.91100(19) 0.0245(5) Uani d . . . 1 . .
F F1 0.80731(17) 0.48096(9) 0.9239(2) 0.0646(6) Uani d . . . 1 . .
F F2 0.78772(15) 0.45975(10) 0.75238(16) 0.0572(6) Uani d . . . 1 . .
F F3 0.99402(16) 0.42133(9) 0.9071(2) 0.0668(6) Uani d . . . 1 . .
F F4 0.93249(18) 0.37641(10) 0.75888(17) 0.0617(6) Uani d . . . 1 . .
F F5 0.91032(16) 0.33876(11) 1.02792(16) 0.0658(6) Uani d . . . 1 . .
F F6 0.91791(15) 0.28223(8) 0.8824(2) 0.0650(6) Uani d . . . 1 . .
N N1 0.54549(17) 0.43734(10) 0.77134(17) 0.0275(5) Uani d . . . 1 . .
N N2 0.59127(17) 0.26674(9) 0.85051(17) 0.0258(5) Uani d . . . 1 . .
S S1 0.39091(6) 0.43534(3) 0.90808(6) 0.0356(2) Uani d . . . 1 . .
S S2 0.58829(6) 0.17664(3) 0.98864(6) 0.0337(2) Uani d . . . 1 . .
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C2 C1 . . 129.8(2) ?
C3 C2 S1 . . 108.84(19) ?
C1 C2 S1 . . 121.3(2) ?
C2 C3 N1 . . 116.6(2) ?
C2 C3 C29 . . 123.8(2) ?
N1 C3 C29 . . 119.6(2) ?
N1 C4 C5 . . 124.5(2) ?
N1 C4 S1 . . 114.12(19) ?
C5 C4 S1 . . 121.34(19) ?
C10 C5 C6 . . 119.4(2) ?
C10 C5 C4 . . 121.2(2) ?
C6 C5 C4 . . 119.4(2) ?
C7 C6 C5 . . 119.4(2) ?
C6 C7 C8 . . 120.7(3) ?
C9 C8 C7 . . 121.1(2) ?
C8 C9 C10 . . 117.7(2) ?
C8 C9 C11 . . 122.2(2) ?
C10 C9 C11 . . 120.0(2) ?
C5 C10 C9 . . 121.8(2) ?
C14 C11 C13 . . 109.4(3) ?
C14 C11 C9 . . 110.5(2) ?
C13 C11 C9 . . 112.5(3) ?
C14 C11 C12 . . 110.3(3) ?
C13 C11 C12 . . 107.0(3) ?
C9 C11 C12 . . 107.0(2) ?
C17 C16 C15 . . 131.8(3) ?
C17 C16 S2 . . 109.16(19) ?
C15 C16 S2 . . 119.0(2) ?
C16 C17 N2 . . 115.6(2) ?
C16 C17 C33 . . 129.1(2) ?
N2 C17 C33 . . 115.3(2) ?
N2 C18 C19 . . 124.0(2) ?
N2 C18 S2 . . 113.97(19) ?
C19 C18 S2 . . 121.97(19) ?
C24 C19 C20 . . 120.0(2) ?
C24 C19 C18 . . 121.0(2) ?
C20 C19 C18 . . 119.0(2) ?
C21 C20 C19 . . 121.7(2) ?
C20 C21 C22 . . 117.2(3) ?
C20 C21 C25 . . 122.9(2) ?
C22 C21 C25 . . 119.9(2) ?
C23 C22 C21 . . 121.5(3) ?
C22 C23 C24 . . 120.7(3) ?
C23 C24 C19 . . 118.9(3) ?
C27 C25 C21 . . 112.5(2) ?
C27 C25 C28 . . 108.6(3) ?
C21 C25 C28 . . 108.4(2) ?
C27 C25 C26 . . 108.3(3) ?
C21 C25 C26 . . 109.8(3) ?
C28 C25 C26 . . 109.2(3) ?
C33 C29 C3 . . 127.3(2) ?
C33 C29 C30 . . 111.3(2) ?
C3 C29 C30 . . 121.3(2) ?
F1 C30 F2 . . 105.5(2) ?
F1 C30 C29 . . 111.9(2) ?
F2 C30 C29 . . 113.5(2) ?
F1 C30 C31 . . 110.1(2) ?
F2 C30 C31 . . 110.6(2) ?
C29 C30 C31 . . 105.3(2) ?
F3 C31 F4 . . 106.1(2) ?
F3 C31 C30 . . 115.5(2) ?
F4 C31 C30 . . 108.0(2) ?
F3 C31 C32 . . 114.8(2) ?
F4 C31 C32 . . 107.5(2) ?
C30 C31 C32 . . 104.7(2) ?
F6 C32 F5 . . 106.3(2) ?
F6 C32 C33 . . 113.9(2) ?
F5 C32 C33 . . 111.6(2) ?
F6 C32 C31 . . 112.7(2) ?
F5 C32 C31 . . 107.1(2) ?
C33 C32 C31 . . 105.1(2) ?
C29 C33 C17 . . 126.0(2) ?
C29 C33 C32 . . 110.7(2) ?
C17 C33 C32 . . 123.0(2) ?
C4 N1 C3 . . 110.2(2) ?
C18 N2 C17 . . 111.0(2) ?
C2 S1 C4 . . 90.28(12) ?
C16 S2 C18 . . 90.24(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.497(4) ?
C2 C3 . 1.362(4) ?
C2 S1 . 1.717(3) ?
C3 N1 . 1.389(3) ?
C3 C29 . 1.473(3) ?
C4 N1 . 1.307(3) ?
C4 C5 . 1.473(4) ?
C4 S1 . 1.738(3) ?
C5 C10 . 1.389(4) ?
C5 C6 . 1.394(4) ?
C6 C7 . 1.383(4) ?
C7 C8 . 1.388(4) ?
C8 C9 . 1.384(4) ?
C9 C10 . 1.399(4) ?
C9 C11 . 1.533(4) ?
C11 C14 . 1.495(5) ?
C11 C13 . 1.527(5) ?
C11 C12 . 1.536(5) ?
C15 C16 . 1.503(4) ?
C16 C17 . 1.367(4) ?
C16 S2 . 1.718(3) ?
C17 N2 . 1.387(3) ?
C17 C33 . 1.468(3) ?
C18 N2 . 1.304(3) ?
C18 C19 . 1.469(4) ?
C18 S2 . 1.733(3) ?
C19 C24 . 1.388(4) ?
C19 C20 . 1.394(4) ?
C20 C21 . 1.387(4) ?
C21 C22 . 1.405(4) ?
C21 C25 . 1.526(4) ?
C22 C23 . 1.373(5) ?
C23 C24 . 1.387(4) ?
C25 C27 . 1.525(4) ?
C25 C28 . 1.533(4) ?
C25 C26 . 1.534(4) ?
C29 C33 . 1.345(3) ?
C29 C30 . 1.500(4) ?
C30 F1 . 1.344(3) ?
C30 F2 . 1.347(3) ?
C30 C31 . 1.528(4) ?
C31 F3 . 1.308(3) ?
C31 F4 . 1.372(4) ?
C31 C32 . 1.530(4) ?
C32 F6 . 1.328(3) ?
C32 F5 . 1.362(3) ?
C32 C33 . 1.503(3) ?
