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#$Date: 2022-06-27 12:36:48 +0300 (Mon, 27 Jun 2022) $
#$Revision: 276290 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105538.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_8105538
loop_
_publ_author_name
'Liu, Fangfang'
'Li, Hui'
'Pu, Shouzhi'
_publ_section_title
;
 Structure and photochromism of
 1-[2-methyl-5-phenyl-3-thienyl]-2-[2-methyl-5-(4-chlorophenyl)-3-thienyl]3,3,4,4,5,5-hexafluorocyclopent-1-ene,
 C27H16ClF6S2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              49
_journal_page_last               51
_journal_paper_doi               10.1515/ncrs-2018-0129
_journal_volume                  234
_journal_year                    2018
_chemical_formula_sum            'C27 H17 Cl F6 S2'
_chemical_formula_weight         554.98
_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_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 96.1260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.1193(5)
_cell_length_b                   9.2419(2)
_cell_length_c                   10.8343(2)
_cell_measurement_reflns_used    9524
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.36
_cell_volume                     2401.26(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29699
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.783
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.701
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4217
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.701
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0292
_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)+(0.0751P)²+3.7426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3900
_reflns_number_total             4217
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0129_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105538
_shelx_shelxl_version_number     2018/1
_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_min   0.925
_shelx_estimated_absorpt_t_max   0.947
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_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 0.37308(2) 0.71339(5) 0.25566(4) 0.02337(12) Uani 1 1 d . . . . .
S2 S 0.12011(2) 0.68287(5) 0.13666(4) 0.02242(12) Uani 1 1 d . . . . .
F1 F 0.32629(5) 0.17687(11) 0.36073(10) 0.0313(3) Uani 1 1 d . . . . .
F2 F 0.34570(4) 0.18805(12) 0.16997(11) 0.0333(3) Uani 1 1 d . . . . .
F3 F 0.23206(4) 0.05698(12) 0.30340(10) 0.0310(3) Uani 1 1 d . . . . .
F4 F 0.27113(5) -0.01149(11) 0.14093(11) 0.0329(3) Uani 1 1 d . . . . .
F5 F 0.16042(4) 0.16134(11) 0.13688(10) 0.0258(2) Uani 1 1 d . . . . .
F6 F 0.22032(4) 0.18347(11) 0.00180(9) 0.0254(2) Uani 1 1 d . . . . .
C1A C 0.52048(8) 0.7049(2) 0.66298(17) 0.0294(4) Uani 0.5 1 d . . P A 1
H1A H 0.550787 0.725778 0.723759 0.035 Uiso 0.9412(11) 1 calc R U P B 1
C1B C 0.52048(8) 0.7049(2) 0.66298(17) 0.0294(4) Uani 0.5 1 d . . P A 2
Cl1B Cl 0.5597(3) 0.7097(9) 0.7815(7) 0.02855(14) Uani 0.0588(11) 1 d . . P A 2
C2 C 0.49086(7) 0.5782(2) 0.66926(16) 0.0259(4) Uani 1 1 d . . . . .
H2A H 0.501101 0.511430 0.734433 0.031 Uiso 1 1 calc R U . A 1
C3 C 0.44647(7) 0.54685(19) 0.58206(15) 0.0215(4) Uani 1 1 d . . . . .
H3A H 0.426437 0.459073 0.588019 0.026 Uiso 1 1 calc R U . . .
C4 C 0.43069(7) 0.64346(18) 0.48472(15) 0.0191(3) Uani 1 1 d . . . . .
C5 C 0.46112(8) 0.7715(2) 0.47953(17) 0.0275(4) Uani 1 1 d . . . . .
H5A H 0.451205 0.839163 0.414953 0.033 Uiso 1 1 calc R U . . .
C6 C 0.50591(9) 0.8008(2) 0.56820(18) 0.0318(4) Uani 1 1 d . . . . .
H6A H 0.526513 0.887810 0.563078 0.038 Uiso 1 1 calc R U . A 1
C7 C 0.38576(7) 0.60683(18) 0.38729(15) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.35210(7) 0.48766(18) 0.37712(15) 0.0181(3) Uani 1 1 d . . . . .
H8A H 0.352720 0.415231 0.439473 0.022 Uiso 1 1 calc R U . . .
C9 C 0.31584(7) 0.48211(18) 0.26385(15) 0.0181(3) Uani 1 1 d . . . . .
C10 C 0.32261(7) 0.59844(19) 0.18772(15) 0.0207(4) Uani 1 1 d . . . . .
C11 C 0.29521(8) 0.6321(2) 0.06037(16) 0.0276(4) Uani 1 1 d . . . . .
H11A H 0.320641 0.689517 0.015309 0.041 Uiso 1 1 calc R U . . .
H11B H 0.260917 0.687105 0.066981 0.041 Uiso 1 1 calc R U . . .
H11C H 0.286133 0.541633 0.015487 0.041 Uiso 1 1 calc R U . . .
C12 C 0.27970(7) 0.35784(18) 0.22747(14) 0.0170(3) Uani 1 1 d . . . . .
C13 C 0.30385(7) 0.20797(19) 0.24387(16) 0.0214(4) Uani 1 1 d . . . . .
C14 C 0.25558(7) 0.10461(18) 0.20313(16) 0.0215(4) Uani 1 1 d . . . . .
C15 C 0.21355(7) 0.20163(18) 0.12480(15) 0.0189(3) Uani 1 1 d . . . . .
C16 C 0.22780(7) 0.35367(17) 0.16719(14) 0.0167(3) Uani 1 1 d . . . . .
C17 C 0.18632(6) 0.46728(17) 0.13401(15) 0.0171(3) Uani 1 1 d . . . . .
C18 C 0.17557(7) 0.58444(18) 0.20637(15) 0.0198(3) Uani 1 1 d . . . . .
C19 C 0.20263(8) 0.6322(2) 0.33027(16) 0.0250(4) Uani 1 1 d . . . . .
H19A H 0.175043 0.681121 0.375786 0.038 Uiso 1 1 calc R U . . .
H19B H 0.233174 0.699079 0.318695 0.038 Uiso 1 1 calc R U . . .
H19C H 0.217397 0.547664 0.377528 0.038 Uiso 1 1 calc R U . . .
C20 C 0.14904(6) 0.45925(17) 0.02259(15) 0.0174(3) Uani 1 1 d . . . . .
H20A H 0.150827 0.384775 -0.037293 0.021 Uiso 1 1 calc R U . . .
C21 C 0.11062(7) 0.56814(18) 0.00982(15) 0.0191(3) Uani 1 1 d . . . . .
C22 C 0.06448(7) 0.58663(18) -0.08859(15) 0.0188(3) Uani 1 1 d . . . . .
C23 C 0.06762(7) 0.52516(19) -0.20523(16) 0.0225(4) Uani 1 1 d . . . . .
H23A H 0.100767 0.476694 -0.221803 0.027 Uiso 1 1 calc R U . . .
C24 C 0.02325(7) 0.53359(19) -0.29729(16) 0.0237(4) Uani 1 1 d . . . . .
H24A H 0.025849 0.491380 -0.376420 0.028 Uiso 1 1 calc R U . C 1
C25A C -0.02487(7) 0.60417(19) -0.27259(16) 0.0228(4) Uani 0.5 1 d . . P B 1
Cl1A Cl -0.08077(2) 0.61294(6) -0.38711(4) 0.02855(14) Uani 0.9412(11) 1 d . . P
B 1
C25B C -0.02487(7) 0.60417(19) -0.27259(16) 0.0228(4) Uani 0.5 1 d . . P B 2
H25B H -0.055508 0.609410 -0.335264 0.027 Uiso 0.0588(11) 1 calc R U P B 2
C26 C -0.02922(7) 0.66724(19) -0.15845(17) 0.0238(4) Uani 1 1 d . . . . .
H26A H -0.062463 0.715819 -0.142785 0.029 Uiso 1 1 calc R U . B 1
C27 C 0.01537(7) 0.65887(19) -0.06725(16) 0.0224(4) Uani 1 1 d . . . . .
H27A H 0.012636 0.702835 0.011126 0.027 Uiso 1 1 calc R U . . .
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'
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'
Cl Cl 0.1484 0.1585 '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
C10 S1 C7 93.20(8) . .
C18 S2 C21 93.17(8) . .
C6 C1A C2 119.54(17) . .
C6 C1B C2 119.54(17) . .
C6 C1B Cl1B 134.7(3) . .
C2 C1B Cl1B 105.3(3) . .
C1B C2 C3 120.84(17) . .
C1A C2 C3 120.84(17) . .
C2 C3 C4 120.62(17) . .
C5 C4 C3 117.88(16) . .
C5 C4 C7 121.11(16) . .
C3 C4 C7 120.90(16) . .
C6 C5 C4 120.61(17) . .
C1B C6 C5 120.49(18) . .
C1A C6 C5 120.49(18) . .
C8 C7 C4 129.06(15) . .
C8 C7 S1 109.92(12) . .
C4 C7 S1 120.80(13) . .
C7 C8 C9 113.71(15) . .
C10 C9 C8 112.69(15) . .
C10 C9 C12 123.70(15) . .
C8 C9 C12 123.30(15) . .
C9 C10 C11 130.23(16) . .
C9 C10 S1 110.48(12) . .
C11 C10 S1 119.24(13) . .
C16 C12 C9 130.17(15) . .
C16 C12 C13 110.98(14) . .
C9 C12 C13 118.44(14) . .
F1 C13 F2 105.83(13) . .
F1 C13 C12 114.62(14) . .
F2 C13 C12 110.82(14) . .
F1 C13 C14 110.63(14) . .
F2 C13 C14 109.46(14) . .
C12 C13 C14 105.47(13) . .
F4 C14 F3 107.88(14) . .
F4 C14 C13 113.47(14) . .
F3 C14 C13 110.02(14) . .
F4 C14 C15 113.08(14) . .
F3 C14 C15 108.95(14) . .
C13 C14 C15 103.35(13) . .
F5 C15 F6 105.81(13) . .
F5 C15 C16 114.48(13) . .
F6 C15 C16 111.33(13) . .
F5 C15 C14 111.16(13) . .
F6 C15 C14 108.98(13) . .
C16 C15 C14 105.07(13) . .
C12 C16 C17 132.12(15) . .
C12 C16 C15 110.11(14) . .
C17 C16 C15 117.72(14) . .
C18 C17 C20 112.47(14) . .
C18 C17 C16 125.98(15) . .
C20 C17 C16 121.39(14) . .
C17 C18 C19 130.72(15) . .
C17 C18 S2 110.48(12) . .
C19 C18 S2 118.78(13) . .
C21 C20 C17 114.00(15) . .
C20 C21 C22 127.87(15) . .
C20 C21 S2 109.89(12) . .
C22 C21 S2 122.10(12) . .
C23 C22 C27 118.20(16) . .
C23 C22 C21 120.04(15) . .
C27 C22 C21 121.68(15) . .
C24 C23 C22 121.12(16) . .
C25B C24 C23 119.17(16) . .
C25A C24 C23 119.17(16) . .
C26 C25A C24 121.21(16) . .
C26 C25A Cl1A 119.56(13) . .
C24 C25A Cl1A 119.23(14) . .
C26 C25B C24 121.21(16) . .
C25B C26 C27 119.25(16) . .
C25A C26 C27 119.25(16) . .
C26 C27 C22 121.05(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C10 1.7209(17) .
S1 C7 1.7332(16) .
S2 C18 1.7239(17) .
S2 C21 1.7314(17) .
F1 C13 1.354(2) .
F2 C13 1.366(2) .
F3 C14 1.352(2) .
F4 C14 1.342(2) .
F5 C15 1.3541(19) .
F6 C15 1.3701(19) .
C1A C6 1.374(3) .
C1A C2 1.377(3) .
C1B C6 1.374(3) .
C1B C2 1.377(3) .
C1B Cl1B 1.513(7) .
C2 C3 1.381(2) .
C3 C4 1.403(2) .
C4 C5 1.397(3) .
C4 C7 1.469(2) .
C5 C6 1.393(3) .
C7 C8 1.366(2) .
C8 C9 1.430(2) .
C9 C10 1.375(2) .
C9 C12 1.470(2) .
C10 C11 1.497(2) .
C12 C16 1.349(2) .
C12 C13 1.506(2) .
C13 C14 1.534(2) .
C14 C15 1.539(2) .
C15 C16 1.507(2) .
C16 C17 1.468(2) .
C17 C18 1.378(2) .
C17 C20 1.428(2) .
C18 C19 1.495(2) .
C20 C21 1.365(2) .
C21 C22 1.467(2) .
C22 C23 1.395(2) .
C22 C27 1.400(2) .
C23 C24 1.385(2) .
C24 C25B 1.382(2) .
C24 C25A 1.382(2) .
C25A C26 1.381(3) .
C25A Cl1A 1.7341(17) .
C25B C26 1.381(3) .
C26 C27 1.383(2) .
