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#$Date: 2022-03-31 10:31:10 +0300 (Thu, 31 Mar 2022) $
#$Revision: 274163 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104969.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_8104969
loop_
_publ_author_name
'Jiang, Duohua'
_publ_section_title
;
 Crystal structure of
 1-(2-methylphenyl)-2-(2-methylbenzo[b]thienyl)-3,3,4,4,5,5-hexafluorocyclopent-ene,
 C21H14F6S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              89
_journal_page_last               91
_journal_paper_doi               10.1515/ncrs-2021-0393
_journal_volume                  237
_journal_year                    2022
_chemical_formula_sum            'C21 H14 F6 S'
_chemical_formula_weight         412.38
_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   geom
_cell_angle_alpha                90
_cell_angle_beta                 101.0080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9344(11)
_cell_length_b                   16.7106(18)
_cell_length_c                   11.6207(13)
_cell_measurement_reflns_used    7241
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.42
_cell_volume                     1893.7(4)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0159
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14820
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.475
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0491
_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)+(0.0856P)²+0.8069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1541
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2740
_reflns_number_total             3318
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0393_suppl.cif
_cod_data_source_block           140821TXG_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8104969
_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   0.922
_shelx_estimated_absorpt_t_max   0.960
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
C1 C 0.2919(4) 0.2165(2) 0.1952(3) 0.0960(10) Uani 1 1 d . U . . .
H1 H 0.2062 0.2353 0.2038 0.115 Uiso 1 1 calc R U . . .
C2 C 0.2985(3) 0.1503(2) 0.1314(3) 0.0954(10) Uani 1 1 d . . . . .
H2 H 0.2189 0.1237 0.0964 0.115 Uiso 1 1 calc R U . . .
C3 C 0.4235(2) 0.12272(18) 0.1187(3) 0.0730(7) Uani 1 1 d . . . . .
H3 H 0.4290 0.0767 0.0747 0.088 Uiso 1 1 calc R U . . .
C4 C 0.5460(2) 0.16286(13) 0.17137(18) 0.0504(5) Uani 1 1 d . . . . .
C5 C 0.5393(3) 0.23013(16) 0.2357(2) 0.0709(7) Uani 1 1 d . . . . .
C6 C 0.6623(4) 0.2745(2) 0.2896(4) 0.1120(12) Uani 1 1 d . . . . .
H6A H 0.7134 0.2438 0.3530 0.168 Uiso 1 1 calc R U . . .
H6B H 0.6360 0.3247 0.3191 0.168 Uiso 1 1 calc R U . . .
H6C H 0.7181 0.2842 0.2321 0.168 Uiso 1 1 calc R U . . .
C7 C 0.4050(4) 0.2573(2) 0.2476(3) 0.0901(8) Uani 1 1 d . U . . .
H7 H 0.3959 0.3029 0.2914 0.108 Uiso 1 1 calc R U . . .
C8 C 0.6773(2) 0.12904(11) 0.14905(16) 0.0416(4) Uani 1 1 d . . . . .
C9 C 0.7122(2) 0.13644(15) 0.0291(2) 0.0576(6) Uani 1 1 d . . . . .
C10 C 0.8550(3) 0.10295(18) 0.0399(2) 0.0726(8) Uani 1 1 d . . . . .
C11 C 0.8831(3) 0.05995(15) 0.1578(2) 0.0621(6) Uani 1 1 d . . . . .
C12 C 0.77315(19) 0.08805(11) 0.22065(17) 0.0427(4) Uani 1 1 d . . . . .
C13 C 0.7749(2) 0.06330(12) 0.34280(17) 0.0462(5) Uani 1 1 d . . . . .
C14 C 0.8585(2) 0.09500(15) 0.4377(2) 0.0612(6) Uani 1 1 d . . . . .
C15 C 0.9618(3) 0.16077(19) 0.4447(3) 0.0870(9) Uani 1 1 d . . . . .
H15A H 0.9623 0.1809 0.3674 0.131 Uiso 1 1 calc R U . . .
H15B H 1.0511 0.1404 0.4782 0.131 Uiso 1 1 calc R U . . .
H15C H 0.9383 0.2032 0.4930 0.131 Uiso 1 1 calc R U . . .
C16 C 0.6903(2) -0.00101(13) 0.37175(18) 0.0499(5) Uani 1 1 d . . . . .
C17 C 0.7130(3) -0.01466(15) 0.4928(2) 0.0646(6) Uani 1 1 d . . . . .
C18 C 0.6404(4) -0.07443(19) 0.5400(3) 0.0872(10) Uani 1 1 d . . . . .
H18 H 0.6546 -0.0829 0.6205 0.105 Uiso 1 1 calc R U . . .
C19 C 0.5491(4) -0.11969(19) 0.4655(3) 0.0927(10) Uani 1 1 d . . . . .
H19 H 0.5012 -0.1599 0.4958 0.111 Uiso 1 1 calc R U . . .
C20 C 0.5258(4) -0.10737(18) 0.3464(3) 0.0859(9) Uani 1 1 d . . . . .
H20 H 0.4621 -0.1390 0.2975 0.103 Uiso 1 1 calc R U . . .
C21 C 0.5956(3) -0.04866(14) 0.2984(2) 0.0624(6) Uani 1 1 d . . . . .
H21 H 0.5796 -0.0410 0.2177 0.075 Uiso 1 1 calc R U . . .
F1 F 0.6945(6) 0.2072(4) -0.0196(5) 0.0827(17) Uani 0.722(14) 1 d . . P A 1
F1' F 0.743(2) 0.2217(9) 0.0215(17) 0.112(5) Uani 0.278(14) 1 d . . P A 2
F2 F 0.6287(10) 0.0853(4) -0.0493(7) 0.0920(17) Uani 0.722(14) 1 d . . P A 1
F2' F 0.621(2) 0.1239(17) -0.0543(15) 0.108(8) Uani 0.278(14) 1 d . . P A 2
F3 F 0.9418(4) 0.1714(3) 0.0556(6) 0.0972(16) Uani 0.722(14) 1 d . . P A 1
F3' F 0.9435(12) 0.123(2) -0.0027(17) 0.147(11) Uani 0.278(14) 1 d . . P A 2
F4 F 0.8823(6) 0.0666(4) -0.0500(4) 0.1025(19) Uani 0.722(14) 1 d . . P A 1
F4' F 0.810(3) 0.0245(12) -0.0296(16) 0.166(10) Uani 0.278(14) 1 d . . P A 2
F5 F 1.0077(5) 0.0654(4) 0.2135(6) 0.098(2) Uani 0.722(14) 1 d . . P A 1
F5' F 1.0104(13) 0.0901(14) 0.2141(17) 0.121(6) Uani 0.278(14) 1 d . . P A 2
F6 F 0.8716(3) -0.01986(10) 0.1372(2) 0.1201(8) Uani 1 1 d . . . . .
S1 S 0.83501(9) 0.05003(5) 0.56699(5) 0.0820(3) Uani 1 1 d . . . . .
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'
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
C17 S1 C14 92.10(11) . .
C12 C8 C4 129.30(17) . .
C12 C8 C9 111.00(17) . .
C4 C8 C9 119.65(17) . .
C8 C12 C13 128.48(17) . .
C8 C12 C11 110.94(18) . .
C13 C12 C11 120.33(18) . .
C14 C13 C16 113.3(2) . .
C14 C13 C12 124.5(2) . .
C16 C13 C12 122.20(18) . .
C21 C16 C17 118.8(2) . .
C21 C16 C13 129.69(19) . .
C17 C16 C13 111.5(2) . .
C5 C4 C3 119.9(2) . .
C5 C4 C8 123.1(2) . .
C3 C4 C8 116.9(2) . .
C20 C21 C16 119.5(3) . .
C20 C21 H21 120.2 . .
C16 C21 H21 120.2 . .
C13 C14 C15 129.7(2) . .
C13 C14 S1 111.85(19) . .
C15 C14 S1 118.42(19) . .
C2 C3 C4 121.2(3) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
F1 C9 F2 104.8(4) . .
F2' C9 F1' 104.7(10) . .
F2' C9 C8 117.1(10) . .
F1 C9 C8 116.1(3) . .
F2 C9 C8 109.9(4) . .
F1' C9 C8 103.0(7) . .
F2' C9 C10 123.6(11) . .
F1 C9 C10 114.7(3) . .
F2 C9 C10 105.0(4) . .
F1' C9 C10 99.3(9) . .
C8 C9 C10 105.78(18) . .
C16 C17 C18 120.8(3) . .
C16 C17 S1 111.27(19) . .
C18 C17 S1 127.9(2) . .
C4 C5 C7 117.2(3) . .
C4 C5 C6 122.0(3) . .
C7 C5 C6 120.8(3) . .
F5 C11 F6 101.5(4) . .
F6 C11 F5' 118.3(10) . .
F5 C11 C12 116.9(4) . .
F6 C11 C12 110.41(19) . .
F5' C11 C12 109.6(9) . .
F5 C11 C10 114.4(4) . .
F6 C11 C10 108.1(2) . .
F5' C11 C10 104.1(9) . .
C12 C11 C10 105.33(18) . .
C19 C18 C17 118.5(3) . .
C19 C18 H18 120.7 . .
C17 C18 H18 120.7 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C2 C1 C7 122.7(3) . .
C2 C1 H1 118.7 . .
C7 C1 H1 118.7 . .
C18 C19 C20 121.4(3) . .
C18 C19 H19 119.3 . .
C20 C19 H19 119.3 . .
C1 C7 C5 120.1(3) . .
C1 C7 H7 119.9 . .
C5 C7 H7 119.9 . .
F4 C10 F3 105.5(3) . .
F3' C10 C9 130.6(9) . .
F4 C10 C9 116.7(3) . .
F3 C10 C9 104.5(3) . .
F3' C10 C11 120.2(6) . .
F4 C10 C11 118.6(3) . .
F3 C10 C11 105.2(3) . .
C9 C10 C11 104.95(19) . .
F3' C10 F4' 100.6(13) . .
C9 C10 F4' 95.7(8) . .
C11 C10 F4' 93.1(9) . .
C1 C2 C3 118.8(3) . .
C1 C2 H2 120.6 . .
C3 C2 H2 120.6 . .
C19 C20 C21 120.8(3) . .
C19 C20 H20 119.6 . .
C21 C20 H20 119.6 . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C17 1.726(3) .
S1 C14 1.735(3) .
C8 C12 1.329(3) .
C8 C4 1.489(3) .
C8 C9 1.504(3) .
C12 C13 1.475(3) .
C12 C11 1.501(3) .
C13 C14 1.356(3) .
C13 C16 1.443(3) .
C16 C21 1.393(3) .
C16 C17 1.400(3) .
F1 C9 1.309(5) .
C4 C5 1.359(3) .
C4 C3 1.422(4) .
C21 C20 1.379(4) .
C21 H21 0.9300 .
C14 C15 1.495(4) .
C3 C2 1.359(4) .
C3 H3 0.9300 .
F6 C11 1.356(3) .
F5 C11 1.286(6) .
C9 F2' 1.22(2) .
C9 F2 1.400(8) .
C9 F1' 1.463(16) .
C9 C10 1.508(3) .
C17 C18 1.404(4) .
C5 C7 1.440(4) .
C5 C6 1.464(5) .
F4 C10 1.282(5) .
C11 F5' 1.402(14) .
C11 C10 1.524(3) .
C18 C19 1.358(5) .
C18 H18 0.9300 .
F3 C10 1.422(5) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C1 C2 1.341(5) .
C1 C7 1.355(5) .
C1 H1 0.9300 .
C19 C20 1.375(5) .
C19 H19 0.9300 .
C7 H7 0.9300 .
C10 F3' 1.137(10) .
C10 F4' 1.560(16) .
C2 H2 0.9300 .
C20 H20 0.9300 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C4 C8 C12 C13 1.1(4) . . . .
C9 C8 C12 C13 -176.1(2) . . . .
C4 C8 C12 C11 175.3(2) . . . .
C9 C8 C12 C11 -1.9(3) . . . .
C8 C12 C13 C14 -109.0(3) . . . .
C11 C12 C13 C14 77.2(3) . . . .
C8 C12 C13 C16 74.2(3) . . . .
C11 C12 C13 C16 -99.6(2) . . . .
C14 C13 C16 C21 -178.3(2) . . . .
C12 C13 C16 C21 -1.1(3) . . . .
C14 C13 C16 C17 1.1(3) . . . .
C12 C13 C16 C17 178.28(18) . . . .
C12 C8 C4 C5 75.7(3) . . . .
C9 C8 C4 C5 -107.2(2) . . . .
C12 C8 C4 C3 -106.2(3) . . . .
C9 C8 C4 C3 70.9(3) . . . .
C17 C16 C21 C20 0.6(4) . . . .
C13 C16 C21 C20 180.0(2) . . . .
C16 C13 C14 C15 179.0(3) . . . .
C12 C13 C14 C15 1.9(4) . . . .
C16 C13 C14 S1 -1.7(2) . . . .
C12 C13 C14 S1 -178.72(16) . . . .
C17 S1 C14 C13 1.36(19) . . . .
C17 S1 C14 C15 -179.2(2) . . . .
C5 C4 C3 C2 -0.1(4) . . . .
C8 C4 C3 C2 -178.2(2) . . . .
C12 C8 C9 F2' 134.8(15) . . . .
C4 C8 C9 F2' -42.7(15) . . . .
C12 C8 C9 F1 -135.7(4) . . . .
C4 C8 C9 F1 46.7(4) . . . .
C12 C8 C9 F2 105.6(4) . . . .
C4 C8 C9 F2 -71.9(4) . . . .
C12 C8 C9 F1' -111.0(10) . . . .
C4 C8 C9 F1' 71.5(10) . . . .
C12 C8 C9 C10 -7.3(3) . . . .
C4 C8 C9 C10 175.2(2) . . . .
C21 C16 C17 C18 -0.9(4) . . . .
C13 C16 C17 C18 179.6(2) . . . .
C21 C16 C17 S1 179.38(17) . . . .
C13 C16 C17 S1 -0.1(2) . . . .
C14 S1 C17 C16 -0.69(19) . . . .
C14 S1 C17 C18 179.7(3) . . . .
C3 C4 C5 C7 0.3(3) . . . .
C8 C4 C5 C7 178.4(2) . . . .
C3 C4 C5 C6 -178.7(3) . . . .
C8 C4 C5 C6 -0.6(4) . . . .
C8 C12 C11 F5 138.4(4) . . . .
C13 C12 C11 F5 -46.8(4) . . . .
C8 C12 C11 F6 -106.3(2) . . . .
C13 C12 C11 F6 68.5(3) . . . .
C8 C12 C11 F5' 121.6(10) . . . .
C13 C12 C11 F5' -63.6(10) . . . .
C8 C12 C11 C10 10.1(3) . . . .
C13 C12 C11 C10 -175.1(2) . . . .
C16 C17 C18 C19 1.0(4) . . . .
S1 C17 C18 C19 -179.4(2) . . . .
C17 C18 C19 C20 -0.8(5) . . . .
C2 C1 C7 C5 0.2(5) . . . .
C4 C5 C7 C1 -0.4(4) . . . .
C6 C5 C7 C1 178.6(3) . . . .
F2' C9 C10 F3' 78(3) . . . .
F1' C9 C10 F3' -37(3) . . . .
C8 C9 C10 F3' -143(2) . . . .
F1 C9 C10 F4 -84.3(6) . . . .
F2 C9 C10 F4 30.3(6) . . . .
C8 C9 C10 F4 146.5(4) . . . .
F1 C9 C10 F3 31.8(6) . . . .
F2 C9 C10 F3 146.3(5) . . . .
C8 C9 C10 F3 -97.5(3) . . . .
F2' C9 C10 C11 -126.1(15) . . . .
F1 C9 C10 C11 142.2(4) . . . .
F2 C9 C10 C11 -103.3(4) . . . .
F1' C9 C10 C11 119.3(8) . . . .
C8 C9 C10 C11 12.9(3) . . . .
F2' C9 C10 F4' -31(2) . . . .
F1' C9 C10 F4' -145.9(17) . . . .
C8 C9 C10 F4' 107.7(11) . . . .
F6 C11 C10 F3' -97(2) . . . .
F5' C11 C10 F3' 30(3) . . . .
C12 C11 C10 F3' 145(2) . . . .
F5 C11 C10 F4 83.8(7) . . . .
F6 C11 C10 F4 -28.4(5) . . . .
C12 C11 C10 F4 -146.4(5) . . . .
F5 C11 C10 F3 -33.8(6) . . . .
F6 C11 C10 F3 -146.0(3) . . . .
C12 C11 C10 F3 96.0(3) . . . .
F5 C11 C10 C9 -143.7(4) . . . .
F6 C11 C10 C9 104.1(2) . . . .
F5' C11 C10 C9 -129.2(10) . . . .
C12 C11 C10 C9 -13.9(3) . . . .
F6 C11 C10 F4' 7.4(10) . . . .
F5' C11 C10 F4' 134.0(16) . . . .
C12 C11 C10 F4' -110.7(10) . . . .
C7 C1 C2 C3 0.1(5) . . . .
C4 C3 C2 C1 -0.1(5) . . . .
C18 C19 C20 C21 0.5(5) . . . .
C16 C21 C20 C19 -0.4(5) . . . .
