#------------------------------------------------------------------------------
#$Date: 2022-06-15 09:51:49 +0300 (Wed, 15 Jun 2022) $
#$Revision: 276039 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105419.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_8105419
loop_
_publ_author_name
'Kou, Jianlan'
_publ_section_title
;
 Structure of
 7-(3,3,4,4,5,5-hexafluoro-2-(2-methylbenzo[b]thiophen-3-yl)cyclopent-1-en-1-yl)-8-methylquinoline,
 C24H15F6NS
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1195
_journal_page_last               1197
_journal_paper_doi               10.1515/ncrs-2020-0246
_journal_volume                  235
_journal_year                    2020
_chemical_formula_sum            'C24 H15 F6 N S'
_chemical_formula_weight         463.43
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 119.1850(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5279(11)
_cell_length_b                   21.242(2)
_cell_length_c                   10.7096(11)
_cell_measurement_reflns_used    7339
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      2.22
_cell_volume                     2091.0(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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0171
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16435
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.902
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0488
_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)+(0.0725P)²+0.9903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2954
_reflns_number_total             3670
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0246_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105419
_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   0.945
_shelx_estimated_absorpt_t_max   0.951
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 1.0959(3) 0.34164(17) 0.4542(3) 0.0835(9) Uani 1 1 d . . . . .
H1 H 1.1513 0.3148 0.4314 0.100 Uiso 1 1 calc R U . . .
C2 C 1.1661(3) 0.37325(18) 0.5842(3) 0.0870(9) Uani 1 1 d . . . . .
H2 H 1.2651 0.3673 0.6455 0.104 Uiso 1 1 calc R U . . .
C3 C 1.0893(3) 0.41231(16) 0.6198(3) 0.0759(8) Uani 1 1 d . . . . .
H3 H 1.1349 0.4343 0.7058 0.091 Uiso 1 1 calc R U . . .
C4 C 0.9386(3) 0.42004(12) 0.5263(2) 0.0546(6) Uani 1 1 d . . . . .
C5 C 0.8760(2) 0.38626(10) 0.3960(2) 0.0480(5) Uani 1 1 d . . . . .
N1 N 0.9569(2) 0.34699(11) 0.3612(2) 0.0660(6) Uani 1 1 d . . . . .
C7 C 0.7245(2) 0.39215(10) 0.2954(2) 0.0440(5) Uani 1 1 d . . . . .
C8 C 0.6411(2) 0.43086(10) 0.3304(2) 0.0447(5) Uani 1 1 d . . . . .
C9 C 0.7063(3) 0.46419(11) 0.4626(2) 0.0575(6) Uani 1 1 d . . . . .
H9 H 0.6491 0.4904 0.4845 0.069 Uiso 1 1 calc R U . . .
C10 C 0.8494(3) 0.45847(13) 0.5567(3) 0.0630(6) Uani 1 1 d . . . . .
H10 H 0.8891 0.4803 0.6428 0.076 Uiso 1 1 calc R U . . .
C11 C 0.6653(3) 0.35731(12) 0.1567(2) 0.0565(6) Uani 1 1 d . . . . .
H11A H 0.6452 0.3145 0.1703 0.085 Uiso 1 1 calc R U . . .
H11B H 0.7356 0.3579 0.1241 0.085 Uiso 1 1 calc R U . . .
H11C H 0.5773 0.3772 0.0868 0.085 Uiso 1 1 calc R U . . .
C12 C 0.4836(2) 0.44176(9) 0.2329(2) 0.0445(5) Uani 1 1 d . . . . .
C13 C 0.4277(3) 0.50805(11) 0.1908(3) 0.0567(6) Uani 1 1 d . . . . .
C14 C 0.2718(3) 0.50079(12) 0.0706(3) 0.0667(7) Uani 1 1 d . . . . .
C15 C 0.2296(3) 0.43472(12) 0.0931(3) 0.0596(6) Uani 1 1 d . . . . .
C16 C 0.3725(2) 0.40092(10) 0.1763(2) 0.0479(5) Uani 1 1 d . . . . .
C17 C 0.3752(2) 0.33274(10) 0.2023(3) 0.0519(5) Uani 1 1 d . . . . .
C18 C 0.3390(3) 0.28746(12) 0.0999(3) 0.0717(8) Uani 1 1 d . . . . .
C19 C 0.2985(3) 0.29436(18) -0.0549(4) 0.0958(11) Uani 1 1 d . . . . .
H19A H 0.3156 0.3369 -0.0729 0.144 Uiso 1 1 calc R U . . .
H19B H 0.1974 0.2843 -0.1140 0.144 Uiso 1 1 calc R U . . .
H19C H 0.3566 0.2663 -0.0765 0.144 Uiso 1 1 calc R U . . .
C20 C 0.3977(3) 0.24196(12) 0.3364(4) 0.0791(9) Uani 1 1 d . . . . .
C21 C 0.4116(2) 0.30807(10) 0.3404(3) 0.0575(6) Uani 1 1 d . . . . .
C22 C 0.4542(3) 0.33917(12) 0.4705(3) 0.0609(6) Uani 1 1 d . . . . .
H22 H 0.4642 0.3827 0.4755 0.073 Uiso 1 1 calc R U . . .
C23 C 0.4811(3) 0.30562(16) 0.5900(4) 0.0841(9) Uani 1 1 d . . . . .
H23 H 0.5113 0.3264 0.6764 0.101 Uiso 1 1 calc R U . . .
C24 C 0.4635(4) 0.2405(2) 0.5831(5) 0.1056(13) Uani 1 1 d . . . . .
H24 H 0.4798 0.2184 0.6646 0.127 Uiso 1 1 calc R U . . .
F1 F 0.50921(19) 0.54350(7) 0.1536(2) 0.0874(5) Uani 1 1 d . . . . .
F2 F 0.4252(2) 0.53976(7) 0.30017(18) 0.0895(6) Uani 1 1 d . . . . .
F3 F 0.1823(2) 0.54553(8) 0.0668(3) 0.1131(7) Uani 1 1 d . . . . .
F4 F 0.2720(2) 0.50251(9) -0.05613(18) 0.0980(6) Uani 1 1 d . . . . .
F5 F 0.15824(18) 0.43741(9) 0.1689(2) 0.0891(5) Uani 1 1 d . . . . .
F6 F 0.13701(16) 0.40776(8) -0.03272(17) 0.0807(5) Uani 1 1 d . . . . .
C25 C 0.4231(4) 0.20870(16) 0.4595(6) 0.1060(14) Uani 1 1 d . . . . .
H25 H 0.4123 0.1652 0.4565 0.127 Uiso 1 1 calc R U . . .
S1 S 0.34820(9) 0.21291(3) 0.16844(12) 0.0981(4) 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
N1 C1 C2 124.7(3) . .
C3 C2 C1 119.0(3) . .
C2 C3 C4 119.7(3) . .
C10 C4 C3 123.5(2) . .
C10 C4 C5 118.9(2) . .
C3 C4 C5 117.5(2) . .
N1 C5 C4 121.7(2) . .
N1 C5 C7 117.56(19) . .
C4 C5 C7 120.7(2) . .
C1 N1 C5 117.3(2) . .
C8 C7 C5 118.08(18) . .
C8 C7 C11 123.50(19) . .
C5 C7 C11 118.40(19) . .
C7 C8 C9 120.2(2) . .
C7 C8 C12 122.81(18) . .
C9 C8 C12 116.92(19) . .
C10 C9 C8 121.3(2) . .
C9 C10 C4 120.7(2) . .
C16 C12 C8 130.24(19) . .
C16 C12 C13 109.98(19) . .
C8 C12 C13 119.69(18) . .
F1 C13 F2 105.1(2) . .
F1 C13 C12 113.6(2) . .
F2 C13 C12 111.91(19) . .
F1 C13 C14 112.9(2) . .
F2 C13 C14 108.2(2) . .
C12 C13 C14 105.15(19) . .
F3 C14 F4 107.3(2) . .
F3 C14 C13 114.2(2) . .
F4 C14 C13 108.4(2) . .
F3 C14 C15 114.1(2) . .
F4 C14 C15 108.9(2) . .
C13 C14 C15 103.7(2) . .
F6 C15 F5 106.0(2) . .
F6 C15 C16 114.63(19) . .
F5 C15 C16 110.7(2) . .
F6 C15 C14 110.9(2) . .
F5 C15 C14 110.2(2) . .
C16 C15 C14 104.40(19) . .
C12 C16 C17 128.2(2) . .
C12 C16 C15 111.0(2) . .
C17 C16 C15 120.18(19) . .
C18 C17 C21 113.6(2) . .
C18 C17 C16 124.6(2) . .
C21 C17 C16 121.70(19) . .
C17 C18 C19 129.4(3) . .
C17 C18 S1 111.6(2) . .
C19 C18 S1 119.0(2) . .
C25 C20 C21 120.3(3) . .
C25 C20 S1 128.5(3) . .
C21 C20 S1 111.2(2) . .
C22 C21 C20 118.5(3) . .
C22 C21 C17 130.3(2) . .
C20 C21 C17 111.2(2) . .
C23 C22 C21 120.2(3) . .
C22 C23 C24 120.4(4) . .
C25 C24 C23 121.1(3) . .
C24 C25 C20 119.5(3) . .
C20 S1 C18 92.36(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.313(3) .
C1 C2 1.390(4) .
C2 C3 1.337(4) .
C3 C4 1.413(4) .
C4 C10 1.398(4) .
C4 C5 1.414(3) .
C5 N1 1.367(3) .
C5 C7 1.430(3) .
C7 C8 1.381(3) .
C7 C11 1.496(3) .
C8 C9 1.425(3) .
C8 C12 1.485(3) .
C9 C10 1.348(4) .
C12 C16 1.340(3) .
C12 C13 1.508(3) .
C13 F1 1.340(3) .
C13 F2 1.362(3) .
C13 C14 1.521(4) .
C14 F3 1.324(3) .
C14 F4 1.359(3) .
C14 C15 1.526(4) .
C15 F6 1.347(3) .
C15 F5 1.350(3) .
C15 C16 1.505(3) .
C16 C17 1.472(3) .
C17 C18 1.366(3) .
C17 C21 1.434(4) .
C18 C19 1.503(5) .
C18 S1 1.728(3) .
C20 C25 1.402(5) .
C20 C21 1.410(3) .
C20 S1 1.725(4) .
C21 C22 1.403(4) .
C22 C23 1.369(4) .
C23 C24 1.393(5) .
C24 C25 1.356(6) .
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 C1 C2 C3 -0.1(6) . . . .
C1 C2 C3 C4 0.9(5) . . . .
C2 C3 C4 C10 178.2(3) . . . .
C2 C3 C4 C5 -1.2(4) . . . .
C10 C4 C5 N1 -178.7(2) . . . .
C3 C4 C5 N1 0.6(3) . . . .
C10 C4 C5 C7 1.2(3) . . . .
C3 C4 C5 C7 -179.4(2) . . . .
C2 C1 N1 C5 -0.4(5) . . . .
C4 C5 N1 C1 0.2(4) . . . .
C7 C5 N1 C1 -179.8(2) . . . .
N1 C5 C7 C8 178.9(2) . . . .
C4 C5 C7 C8 -1.0(3) . . . .
N1 C5 C7 C11 -2.4(3) . . . .
C4 C5 C7 C11 177.6(2) . . . .
C5 C7 C8 C9 0.7(3) . . . .
C11 C7 C8 C9 -177.8(2) . . . .
C5 C7 C8 C12 178.50(18) . . . .
C11 C7 C8 C12 -0.1(3) . . . .
C7 C8 C9 C10 -0.6(3) . . . .
C12 C8 C9 C10 -178.5(2) . . . .
C8 C9 C10 C4 0.8(4) . . . .
C3 C4 C10 C9 179.6(3) . . . .
C5 C4 C10 C9 -1.1(4) . . . .
C7 C8 C12 C16 59.2(3) . . . .
C9 C8 C12 C16 -122.9(2) . . . .
C7 C8 C12 C13 -124.5(2) . . . .
C9 C8 C12 C13 53.3(3) . . . .
C16 C12 C13 F1 -137.6(2) . . . .
C8 C12 C13 F1 45.4(3) . . . .
C16 C12 C13 F2 103.5(2) . . . .
C8 C12 C13 F2 -73.5(3) . . . .
C16 C12 C13 C14 -13.8(2) . . . .
C8 C12 C13 C14 169.24(19) . . . .
F1 C13 C14 F3 -88.4(3) . . . .
F2 C13 C14 F3 27.5(3) . . . .
C12 C13 C14 F3 147.2(2) . . . .
F1 C13 C14 F4 31.2(3) . . . .
F2 C13 C14 F4 147.1(2) . . . .
C12 C13 C14 F4 -93.2(2) . . . .
F1 C13 C14 C15 146.8(2) . . . .
F2 C13 C14 C15 -97.3(2) . . . .
C12 C13 C14 C15 22.5(2) . . . .
F3 C14 C15 F6 88.1(3) . . . .
F4 C14 C15 F6 -31.8(3) . . . .
C13 C14 C15 F6 -147.1(2) . . . .
F3 C14 C15 F5 -29.0(3) . . . .
F4 C14 C15 F5 -148.9(2) . . . .
C13 C14 C15 F5 95.8(2) . . . .
F3 C14 C15 C16 -147.9(2) . . . .
F4 C14 C15 C16 92.2(2) . . . .
C13 C14 C15 C16 -23.1(2) . . . .
C8 C12 C16 C17 3.9(4) . . . .
C13 C12 C16 C17 -172.7(2) . . . .
C8 C12 C16 C15 175.2(2) . . . .
C13 C12 C16 C15 -1.3(3) . . . .
F6 C15 C16 C12 137.4(2) . . . .
F5 C15 C16 C12 -102.8(2) . . . .
C14 C15 C16 C12 15.8(3) . . . .
F6 C15 C16 C17 -50.4(3) . . . .
F5 C15 C16 C17 69.4(3) . . . .
C14 C15 C16 C17 -172.0(2) . . . .
C12 C16 C17 C18 -118.4(3) . . . .
C15 C16 C17 C18 71.0(3) . . . .
C12 C16 C17 C21 64.2(3) . . . .
C15 C16 C17 C21 -106.4(2) . . . .
C21 C17 C18 C19 -178.4(2) . . . .
C16 C17 C18 C19 4.0(4) . . . .
C21 C17 C18 S1 0.0(3) . . . .
C16 C17 C18 S1 -177.61(17) . . . .
C25 C20 C21 C22 1.4(4) . . . .
S1 C20 C21 C22 -178.75(17) . . . .
C25 C20 C21 C17 -177.6(2) . . . .
S1 C20 C21 C17 2.2(2) . . . .
C18 C17 C21 C22 179.7(2) . . . .
C16 C17 C21 C22 -2.7(3) . . . .
C18 C17 C21 C20 -1.4(3) . . . .
C16 C17 C21 C20 176.27(19) . . . .
C20 C21 C22 C23 -0.2(3) . . . .
C17 C21 C22 C23 178.7(2) . . . .
C21 C22 C23 C24 -1.3(4) . . . .
C22 C23 C24 C25 1.6(5) . . . .
C23 C24 C25 C20 -0.4(5) . . . .
C21 C20 C25 C24 -1.2(5) . . . .
S1 C20 C25 C24 179.1(3) . . . .
C25 C20 S1 C18 177.9(3) . . . .
C21 C20 S1 C18 -1.90(19) . . . .
C17 C18 S1 C20 1.1(2) . . . .
C19 C18 S1 C20 179.7(2) . . . .
