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#$Date: 2022-06-24 10:17:54 +0300 (Fri, 24 Jun 2022) $
#$Revision: 276224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105493.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_8105493
loop_
_publ_author_name
'Li, Ying'
_publ_section_title
;
 Crystal structure of
 4-(2-(benzo[b]thiophen-2-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl)-1,5-dimethyl-1H-pyrrole-2-carbonitrile,
 C20H12F6N2S
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1457
_journal_page_last               1459
_journal_paper_doi               10.1515/ncrs-2020-0357
_journal_volume                  235
_journal_year                    2020
_chemical_formula_sum            'C20 H12 F6 N2 S'
_chemical_formula_weight         426.38
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.0670(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2091(9)
_cell_length_b                   13.9215(16)
_cell_length_c                   16.5280(19)
_cell_measurement_reflns_used    8489
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.47
_cell_volume                     1884.1(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 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0182
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18010
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_min         2.487
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4356
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0421
_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)+(0.0713P)²+0.4604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3687
_reflns_number_total             4356
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0357_suppl.cif
_cod_data_source_block           141029TXG_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105493
_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_min   0.937
_shelx_estimated_absorpt_t_max   0.954
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
C1 C -0.1755(3) 0.86114(17) 0.07026(11) 0.0677(6) Uani 1 1 d . . . . .
C2 C -0.1269(2) 0.82242(13) 0.14828(9) 0.0476(4) Uani 1 1 d . . . . .
C3 C -0.0162(2) 0.85753(11) 0.20697(10) 0.0437(3) Uani 1 1 d . . . . .
H3 H 0.0455 0.9133 0.2042 0.052 Uiso 1 1 calc R U . . .
C4 C -0.01451(17) 0.79227(10) 0.27235(8) 0.0365(3) Uani 1 1 d . . . . .
C5 C -0.12736(18) 0.72070(11) 0.25162(9) 0.0416(3) Uani 1 1 d . . . . .
C6 C -0.1802(3) 0.63793(15) 0.29988(14) 0.0671(5) Uani 1 1 d . . . . .
H6A H -0.2918 0.6469 0.3122 0.101 Uiso 1 1 calc R U . . .
H6B H -0.1122 0.6335 0.3494 0.101 Uiso 1 1 calc R U . . .
H6C H -0.1710 0.5798 0.2692 0.101 Uiso 1 1 calc R U . . .
C7 C -0.3168(3) 0.68110(18) 0.12987(14) 0.0750(6) Uani 1 1 d . . . . .
H7A H -0.2733 0.6182 0.1211 0.112 Uiso 1 1 calc R U . . .
H7B H -0.3455 0.7111 0.0785 0.112 Uiso 1 1 calc R U . . .
H7C H -0.4122 0.6757 0.1600 0.112 Uiso 1 1 calc R U . . .
C8 C 0.08297(18) 0.79983(10) 0.34993(8) 0.0383(3) Uani 1 1 d . . . . .
C9 C 0.0515(3) 0.88028(13) 0.40666(11) 0.0582(5) Uani 1 1 d . . . . .
C10 C 0.1807(3) 0.87134(16) 0.47714(13) 0.0750(7) Uani 1 1 d . . . . .
C11 C 0.2611(2) 0.77387(13) 0.46559(10) 0.0537(4) Uani 1 1 d . . . . .
C12 C 0.20136(18) 0.74064(10) 0.38180(8) 0.0370(3) Uani 1 1 d . . . . .
C13 C 0.27349(17) 0.65632(10) 0.34747(8) 0.0357(3) Uani 1 1 d . . . . .
C14 C 0.38676(19) 0.59696(11) 0.38594(9) 0.0433(3) Uani 1 1 d . . . . .
H14 H 0.4274 0.6058 0.4394 0.052 Uiso 1 1 calc R U . . .
C15 C 0.43647(17) 0.52046(10) 0.33646(9) 0.0401(3) Uani 1 1 d . . . . .
C16 C 0.35896(17) 0.52418(10) 0.25837(9) 0.0397(3) Uani 1 1 d . . . . .
C17 C 0.5482(2) 0.44610(13) 0.35670(12) 0.0537(4) Uani 1 1 d . . . . .
H17 H 0.6033 0.4438 0.4078 0.064 Uiso 1 1 calc R U . . .
C18 C 0.5746(2) 0.37725(13) 0.29989(14) 0.0600(5) Uani 1 1 d . . . . .
H18 H 0.6470 0.3273 0.3130 0.072 Uiso 1 1 calc R U . . .
C19 C 0.4946(2) 0.38108(13) 0.22288(15) 0.0642(5) Uani 1 1 d . . . . .
H19 H 0.5135 0.3330 0.1856 0.077 Uiso 1 1 calc R U . . .
C20 C 0.3877(2) 0.45464(13) 0.20036(12) 0.0562(4) Uani 1 1 d . . . . .
H20 H 0.3367 0.4576 0.1483 0.067 Uiso 1 1 calc R U . . .
F1 F -0.0996(9) 0.8656(6) 0.4382(4) 0.0839(14) Uani 0.70(2) 1 d . . P A 1
F2 F 0.0404(7) 0.9665(5) 0.3717(4) 0.0759(12) Uani 0.70(2) 1 d . . P A 1
F3 F 0.1399(15) 0.8904(7) 0.5478(3) 0.111(3) Uani 0.70(2) 1 d . U P A 1
F4 F 0.3043(10) 0.9414(3) 0.4606(7) 0.103(2) Uani 0.70(2) 1 d . U P A 1
F5 F 0.2187(2) 0.71229(10) 0.52347(7) 0.0913(5) Uani 1 1 d . . . . .
F6 F 0.42441(16) 0.78170(11) 0.47524(8) 0.0873(5) Uani 1 1 d . . . . .
F1' F -0.090(2) 0.896(2) 0.4246(13) 0.116(7) Uani 0.30(2) 1 d . . P A 2
F2' F 0.107(5) 0.9656(10) 0.3704(11) 0.115(6) Uani 0.30(2) 1 d . . P A 2
F3' F 0.0709(18) 0.8475(15) 0.5473(8) 0.089(4) Uani 0.30(2) 1 d . . P A 2
F4' F 0.2552(17) 0.9358(8) 0.5043(14) 0.100(5) Uani 0.30(2) 1 d . . P A 2
N1 N -0.19367(16) 0.73944(10) 0.17574(8) 0.0472(3) Uani 1 1 d . . . . .
N2 N -0.2168(3) 0.8918(2) 0.00819(12) 0.1047(8) Uani 1 1 d . . . . .
S1 S 0.22644(5) 0.62123(3) 0.24677(2) 0.04313(13) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 C1 C2 178.9(3) . .
N1 C2 C3 109.08(14) . .
N1 C2 C1 121.66(17) . .
C3 C2 C1 129.26(19) . .
C2 C3 C4 106.40(15) . .
C2 C3 H3 126.8 . .
C4 C3 H3 126.8 . .
C5 C4 C3 107.65(13) . .
C5 C4 C8 125.54(13) . .
C3 C4 C8 126.77(14) . .
N1 C5 C4 107.91(14) . .
N1 C5 C6 122.19(15) . .
C4 C5 C6 129.86(15) . .
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 . .
N1 C7 H7A 109.5 . .
N1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C12 C8 C4 129.01(13) . .
C12 C8 C9 111.32(13) . .
C4 C8 C9 119.63(13) . .
F2 C9 F1 105.0(4) . .
F1' C9 F2' 106.7(9) . .
F1' C9 C8 119.2(10) . .
F2 C9 C8 114.3(3) . .
F1 C9 C8 108.8(4) . .
F2' C9 C8 106.7(9) . .
F1' C9 C10 116.5(9) . .
F2 C9 C10 115.3(3) . .
F1 C9 C10 106.9(3) . .
F2' C9 C10 99.5(11) . .
C8 C9 C10 106.05(14) . .
F3 C10 F4 105.6(3) . .
F4' C10 C9 123.6(9) . .
F3 C10 C9 118.2(4) . .
F4 C10 C9 105.0(3) . .
F4' C10 C11 121.0(5) . .
F3 C10 C11 116.5(3) . .
F4 C10 C11 105.1(4) . .
C9 C10 C11 105.10(14) . .
F4' C10 F3' 101.2(7) . .
C9 C10 F3' 100.3(6) . .
C11 C10 F3' 100.5(6) . .
F6 C11 F5 105.83(15) . .
F6 C11 C12 112.98(15) . .
F5 C11 C12 111.90(16) . .
F6 C11 C10 110.46(17) . .
F5 C11 C10 109.93(17) . .
C12 C11 C10 105.79(13) . .
C8 C12 C13 130.07(13) . .
C8 C12 C11 110.40(13) . .
C13 C12 C11 119.53(12) . .
C14 C13 C12 126.25(13) . .
C14 C13 S1 111.74(11) . .
C12 C13 S1 121.98(10) . .
C13 C14 C15 113.53(13) . .
C13 C14 H14 123.2 . .
C15 C14 H14 123.2 . .
C16 C15 C17 119.51(15) . .
C16 C15 C14 111.91(13) . .
C17 C15 C14 128.58(15) . .
C20 C16 C15 121.37(15) . .
C20 C16 S1 126.83(13) . .
C15 C16 S1 111.78(11) . .
C18 C17 C15 118.94(18) . .
C18 C17 H17 120.5 . .
C15 C17 H17 120.5 . .
C17 C18 C19 120.85(16) . .
C17 C18 H18 119.6 . .
C19 C18 H18 119.6 . .
C20 C19 C18 121.62(17) . .
C20 C19 H19 119.2 . .
C18 C19 H19 119.2 . .
C19 C20 C16 117.67(18) . .
C19 C20 H20 121.2 . .
C16 C20 H20 121.2 . .
C5 N1 C2 108.95(13) . .
C5 N1 C7 126.05(17) . .
C2 N1 C7 125.00(16) . .
C16 S1 C13 91.03(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.140(3) .
C1 C2 1.428(2) .
C2 N1 1.370(2) .
C2 C3 1.371(2) .
C3 C4 1.411(2) .
C3 H3 0.9300 .
C4 C5 1.387(2) .
C4 C8 1.4662(19) .
C5 N1 1.357(2) .
C5 C6 1.484(2) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 N1 1.465(2) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 C12 1.3522(19) .
C8 C9 1.495(2) .
C9 F1' 1.242(19) .
C9 F2 1.333(7) .
C9 F1 1.394(7) .
C9 F2' 1.42(2) .
C9 C10 1.524(3) .
C10 F4' 1.158(9) .
C10 F3 1.265(7) .
C10 F4 1.447(8) .
C10 C11 1.527(3) .
C10 F3' 1.554(10) .
C11 F6 1.344(2) .
C11 F5 1.348(2) .
C11 C12 1.509(2) .
C12 C13 1.4486(19) .
C13 C14 1.367(2) .
C13 S1 1.7512(14) .
C14 C15 1.420(2) .
C14 H14 0.9300 .
C15 C16 1.399(2) .
C15 C17 1.408(2) .
C16 C20 1.394(2) .
C16 S1 1.7366(15) .
C17 C18 1.370(3) .
C17 H17 0.9300 .
C18 C19 1.391(3) .
C18 H18 0.9300 .
C19 C20 1.382(3) .
C19 H19 0.9300 .
C20 H20 0.9300 .
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
N1 C2 C3 C4 0.75(18) . . . .
C1 C2 C3 C4 179.71(17) . . . .
C2 C3 C4 C5 -1.29(17) . . . .
C2 C3 C4 C8 -178.92(14) . . . .
C3 C4 C5 N1 1.36(17) . . . .
C8 C4 C5 N1 179.02(13) . . . .
C3 C4 C5 C6 -176.32(17) . . . .
C8 C4 C5 C6 1.3(3) . . . .
C5 C4 C8 C12 65.9(2) . . . .
C3 C4 C8 C12 -116.91(19) . . . .
C5 C4 C8 C9 -111.89(18) . . . .
C3 C4 C8 C9 65.3(2) . . . .
C12 C8 C9 F1' -127.7(16) . . . .
C4 C8 C9 F1' 50.4(16) . . . .
C12 C8 C9 F2 134.3(3) . . . .
C4 C8 C9 F2 -47.5(4) . . . .
C12 C8 C9 F1 -108.6(3) . . . .
C4 C8 C9 F1 69.5(3) . . . .
C12 C8 C9 F2' 111.6(14) . . . .
C4 C8 C9 F2' -70.3(14) . . . .
C12 C8 C9 C10 6.1(2) . . . .
C4 C8 C9 C10 -175.74(17) . . . .
F1' C9 C10 F4' -90(3) . . . .
F2' C9 C10 F4' 24(2) . . . .
C8 C9 C10 F4' 134.4(14) . . . .
F2 C9 C10 F3 89.7(8) . . . .
F1 C9 C10 F3 -26.7(9) . . . .
C8 C9 C10 F3 -142.7(7) . . . .
F2 C9 C10 F4 -27.7(6) . . . .
F1 C9 C10 F4 -144.1(6) . . . .
C8 C9 C10 F4 99.9(5) . . . .
F1' C9 C10 C11 124.6(16) . . . .
F2 C9 C10 C11 -138.3(4) . . . .
F1 C9 C10 C11 105.4(4) . . . .
F2' C9 C10 C11 -121.2(11) . . . .
C8 C9 C10 C11 -10.7(2) . . . .
F1' C9 C10 F3' 21(2) . . . .
F2' C9 C10 F3' 134.8(18) . . . .
C8 C9 C10 F3' -114.6(8) . . . .
F4' C10 C11 F6 -12.2(16) . . . .
F3 C10 C11 F6 -93.1(7) . . . .
F4 C10 C11 F6 23.4(4) . . . .
C9 C10 C11 F6 133.94(19) . . . .
F3' C10 C11 F6 -122.2(8) . . . .
F4' C10 C11 F5 104.2(16) . . . .
F3 C10 C11 F5 23.4(7) . . . .
F4 C10 C11 F5 139.8(4) . . . .
C9 C10 C11 F5 -109.6(2) . . . .
F3' C10 C11 F5 -5.8(8) . . . .
F4' C10 C11 C12 -134.8(16) . . . .
F3 C10 C11 C12 144.4(7) . . . .
F4 C10 C11 C12 -99.2(4) . . . .
C9 C10 C11 C12 11.4(2) . . . .
F3' C10 C11 C12 115.2(8) . . . .
C4 C8 C12 C13 4.1(3) . . . .
C9 C8 C12 C13 -177.97(16) . . . .
C4 C8 C12 C11 -176.63(16) . . . .
C9 C8 C12 C11 1.3(2) . . . .
F6 C11 C12 C8 -129.12(16) . . . .
F5 C11 C12 C8 111.55(17) . . . .
C10 C11 C12 C8 -8.2(2) . . . .
F6 C11 C12 C13 50.2(2) . . . .
F5 C11 C12 C13 -69.1(2) . . . .
C10 C11 C12 C13 171.20(17) . . . .
C8 C12 C13 C14 -175.88(17) . . . .
C11 C12 C13 C14 4.9(2) . . . .
C8 C12 C13 S1 6.3(2) . . . .
C11 C12 C13 S1 -172.89(13) . . . .
C12 C13 C14 C15 -179.30(14) . . . .
S1 C13 C14 C15 -1.30(18) . . . .
C13 C14 C15 C16 0.9(2) . . . .
C13 C14 C15 C17 -179.04(16) . . . .
C17 C15 C16 C20 1.2(2) . . . .
C14 C15 C16 C20 -178.70(15) . . . .
C17 C15 C16 S1 179.89(12) . . . .
C14 C15 C16 S1 -0.02(17) . . . .
C16 C15 C17 C18 -2.0(2) . . . .
C14 C15 C17 C18 177.91(16) . . . .
C15 C17 C18 C19 1.0(3) . . . .
C17 C18 C19 C20 0.9(3) . . . .
C18 C19 C20 C16 -1.6(3) . . . .
C15 C16 C20 C19 0.6(3) . . . .
S1 C16 C20 C19 -177.88(14) . . . .
C4 C5 N1 C2 -0.91(17) . . . .
C6 C5 N1 C2 176.99(16) . . . .
C4 C5 N1 C7 179.10(16) . . . .
C6 C5 N1 C7 -3.0(3) . . . .
C3 C2 N1 C5 0.08(18) . . . .
C1 C2 N1 C5 -178.96(15) . . . .
C3 C2 N1 C7 -179.93(17) . . . .
C1 C2 N1 C7 1.0(3) . . . .
C20 C16 S1 C13 178.00(16) . . . .
C15 C16 S1 C13 -0.59(12) . . . .
C14 C13 S1 C16 1.08(12) . . . .
C12 C13 S1 C16 179.17(13) . . . .
