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#$Date: 2022-09-23 11:39:24 +0300 (Fri, 23 Sep 2022) $
#$Revision: 278110 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/58/8105845.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_8105845
loop_
_publ_author_name
'Li, Xiao-Yan'
'Meng, Qing-Guo'
'Hou, Gui-Ge'
_publ_section_title
;
 Crystal structure of
 (3E,5E)-3,5-bis(4-cyanobenzylidene)-1-((4-fluorophenyl)sulfonyl)piperidin-4-one,
 C27H18FN3O3S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              771
_journal_page_last               773
_journal_paper_doi               10.1515/ncrs-2019-0097
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C27 H18 F N3 O3 S'
_chemical_formula_sum            'C27 H18 F N3 O3 S'
_chemical_formula_weight         483.50
_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
_cell_angle_alpha                90
_cell_angle_beta                 107.806(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.091(6)
_cell_length_b                   42.84(3)
_cell_length_c                   7.096(6)
_cell_measurement_reflns_used    2128
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      44.605
_cell_measurement_theta_min      5.62
_cell_volume                     2342(3)
_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, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_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  0.0849
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12141
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         0.951
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0616
_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)+(0.0513P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1321
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2639
_reflns_number_total             4354
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0097_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105845
_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   0.973
_shelx_estimated_absorpt_t_max   0.991
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 0.4144(4) 0.05423(7) 0.8923(5) 0.0383(8) Uani 1 1 d . . . . .
C2 C 0.3696(5) 0.02551(7) 0.7924(5) 0.0423(8) Uani 1 1 d . . . . .
H2 H 0.2532 0.0183 0.7570 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4956(5) 0.00785(8) 0.7457(5) 0.0473(9) Uani 1 1 d . . . . .
H3 H 0.4645 -0.0112 0.6747 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6666(5) 0.01789(8) 0.8026(5) 0.0447(9) Uani 1 1 d . . . . .
C5 C 0.7138(5) 0.04582(7) 0.9054(5) 0.0452(9) Uani 1 1 d . . . . .
H5 H 0.8315 0.0525 0.9461 0.054 Uiso 1 1 calc R U . . .
C6 C 0.5876(4) 0.06378(7) 0.9476(5) 0.0412(8) Uani 1 1 d . . . . .
H6 H 0.6194 0.0830 1.0155 0.049 Uiso 1 1 calc R U . . .
C7 C 0.2767(4) 0.07219(7) 0.9406(5) 0.0414(8) Uani 1 1 d . . . . .
H7 H 0.1932 0.0602 0.9782 0.050 Uiso 1 1 calc R U . . .
C8 C 0.2542(4) 0.10341(7) 0.9382(5) 0.0375(8) Uani 1 1 d . . . . .
C9 C 0.0973(4) 0.11562(7) 0.9836(5) 0.0391(8) Uani 1 1 d . . . . .
C10 C 0.0547(4) 0.14970(7) 0.9537(4) 0.0371(7) Uani 1 1 d . . . . .
C11 C 0.1839(4) 0.17053(7) 0.8963(5) 0.0412(8) Uani 1 1 d . . . . .
H11A H 0.1223 0.1889 0.8234 0.049 Uiso 1 1 calc R U . . .
H11B H 0.2721 0.1781 1.0177 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3705(4) 0.12645(7) 0.8759(5) 0.0439(8) Uani 1 1 d . . . . .
H12A H 0.4630 0.1337 0.9946 0.053 Uiso 1 1 calc R U . . .
H12B H 0.4267 0.1158 0.7877 0.053 Uiso 1 1 calc R U . . .
C13 C -0.0974(4) 0.15965(7) 0.9680(5) 0.0426(8) Uani 1 1 d . . . . .
H13 H -0.1668 0.1444 1.0048 0.051 Uiso 1 1 calc R U . . .
C14 C -0.1714(4) 0.19136(8) 0.9338(5) 0.0420(8) Uani 1 1 d . . . . .
C15 C -0.0730(5) 0.21821(8) 1.0024(5) 0.0469(9) Uani 1 1 d . . . . .
H15 H 0.0458 0.2163 1.0780 0.056 Uiso 1 1 calc R U . . .
C16 C -0.1482(5) 0.24764(8) 0.9607(5) 0.0488(9) Uani 1 1 d . . . . .
H16 H -0.0810 0.2658 1.0094 0.059 Uiso 1 1 calc R U . . .
C17 C -0.3205(5) 0.25055(8) 0.8484(5) 0.0456(9) Uani 1 1 d . . . . .
C18 C -0.4219(5) 0.22393(9) 0.7796(6) 0.0522(9) Uani 1 1 d . . . . .
H18 H -0.5409 0.2258 0.7047 0.063 Uiso 1 1 calc R U . . .
C19 C -0.3455(5) 0.19479(8) 0.8229(5) 0.0499(9) Uani 1 1 d . . . . .
H19 H -0.4134 0.1767 0.7759 0.060 Uiso 1 1 calc R U . . .
C20 C -0.4000(5) 0.28102(9) 0.8010(5) 0.0516(9) Uani 1 1 d . . . . .
C21 C 0.8016(5) -0.00053(8) 0.7561(6) 0.0539(9) Uani 1 1 d . . . . .
C22 C -0.0040(4) 0.12678(7) 0.4859(5) 0.0359(8) Uani 1 1 d . . . . .
C23 C 0.0195(4) 0.09466(7) 0.4719(5) 0.0415(8) Uani 1 1 d . . . . .
H23 H 0.1298 0.0865 0.4759 0.050 Uiso 1 1 calc R U . . .
C24 C -0.1209(5) 0.07466(8) 0.4520(5) 0.0458(9) Uani 1 1 d . . . . .
H24 H -0.1078 0.0527 0.4444 0.055 Uiso 1 1 calc R U . . .
C25 C -0.2787(5) 0.08749(8) 0.4438(5) 0.0451(9) Uani 1 1 d . . . . .
C26 C -0.3065(4) 0.11904(8) 0.4516(5) 0.0467(9) Uani 1 1 d . . . . .
H26 H -0.4183 0.1270 0.4426 0.056 Uiso 1 1 calc R U . . .
C27 C -0.1664(4) 0.13910(7) 0.4732(5) 0.0397(8) Uani 1 1 d . . . . .
H27 H -0.1815 0.1610 0.4791 0.048 Uiso 1 1 calc R U . . .
F1 F -0.4166(3) 0.06807(5) 0.4238(3) 0.0680(6) Uani 1 1 d . . . . .
N1 N 0.2715(3) 0.15380(6) 0.7715(4) 0.0397(6) Uani 1 1 d . . . . .
N2 N 0.9092(5) -0.01436(8) 0.7186(6) 0.0778(11) Uani 1 1 d . . . . .
N3 N -0.4593(4) 0.30522(8) 0.7653(5) 0.0687(10) Uani 1 1 d . . . . .
O1 O 0.0005(3) 0.09806(5) 1.0367(4) 0.0546(7) Uani 1 1 d . . . . .
O2 O 0.2994(3) 0.13803(5) 0.4493(4) 0.0555(7) Uani 1 1 d . . . . .
O3 O 0.1126(3) 0.18305(5) 0.4737(4) 0.0522(6) Uani 1 1 d . . . . .
S1 S 0.17615(10) 0.15208(2) 0.53075(13) 0.0405(2) 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'
O O 0.0106 0.0060 '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
C6 C1 C2 118.6(3) . .
C6 C1 C7 123.0(3) . .
C2 C1 C7 118.3(3) . .
C3 C2 C1 120.0(3) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
C4 C3 C2 120.1(3) . .
C4 C3 H3 119.9 . .
C2 C3 H3 119.9 . .
C3 C4 C5 120.6(3) . .
C3 C4 C21 120.9(3) . .
C5 C4 C21 118.5(3) . .
C6 C5 C4 119.3(3) . .
C6 C5 H5 120.4 . .
C4 C5 H5 120.4 . .
C5 C6 C1 121.4(3) . .
C5 C6 H6 119.3 . .
C1 C6 H6 119.3 . .
C8 C7 C1 128.4(3) . .
C8 C7 H7 115.8 . .
C1 C7 H7 115.8 . .
C7 C8 C9 117.6(3) . .
C7 C8 C12 123.7(3) . .
C9 C8 C12 118.5(3) . .
O1 C9 C8 121.0(3) . .
O1 C9 C10 120.0(3) . .
C8 C9 C10 118.9(3) . .
C13 C10 C9 118.5(3) . .
C13 C10 C11 123.9(3) . .
C9 C10 C11 117.5(3) . .
N1 C11 C10 111.8(2) . .
N1 C11 H11A 109.3 . .
C10 C11 H11A 109.3 . .
N1 C11 H11B 109.3 . .
C10 C11 H11B 109.3 . .
H11A C11 H11B 107.9 . .
N1 C12 C8 111.7(3) . .
N1 C12 H12A 109.3 . .
C8 C12 H12A 109.3 . .
N1 C12 H12B 109.3 . .
C8 C12 H12B 109.3 . .
H12A C12 H12B 107.9 . .
C10 C13 C14 128.2(3) . .
C10 C13 H13 115.9 . .
C14 C13 H13 115.9 . .
C19 C14 C15 118.6(3) . .
C19 C14 C13 118.6(3) . .
C15 C14 C13 122.8(3) . .
C16 C15 C14 120.4(3) . .
C16 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
C17 C16 C15 120.1(3) . .
C17 C16 H16 119.9 . .
C15 C16 H16 119.9 . .
C16 C17 C18 120.4(3) . .
C16 C17 C20 120.8(3) . .
C18 C17 C20 118.7(3) . .
C19 C18 C17 118.8(4) . .
C19 C18 H18 120.6 . .
C17 C18 H18 120.6 . .
C18 C19 C14 121.7(3) . .
C18 C19 H19 119.2 . .
C14 C19 H19 119.2 . .
N3 C20 C17 178.6(4) . .
N2 C21 C4 178.4(4) . .
C27 C22 C23 121.0(3) . .
C27 C22 S1 119.3(2) . .
C23 C22 S1 119.6(2) . .
C24 C23 C22 119.2(3) . .
C24 C23 H23 120.4 . .
C22 C23 H23 120.4 . .
C25 C24 C23 118.4(3) . .
C25 C24 H24 120.8 . .
C23 C24 H24 120.8 . .
F1 C25 C26 117.8(3) . .
F1 C25 C24 118.7(3) . .
C26 C25 C24 123.6(3) . .
C25 C26 C27 118.3(3) . .
C25 C26 H26 120.9 . .
C27 C26 H26 120.9 . .
C26 C27 C22 119.5(3) . .
C26 C27 H27 120.2 . .
C22 C27 H27 120.2 . .
C11 N1 C12 111.6(3) . .
C11 N1 S1 119.0(2) . .
C12 N1 S1 119.5(2) . .
O2 S1 O3 120.58(14) . .
O2 S1 N1 105.97(15) . .
O3 S1 N1 105.37(14) . .
O2 S1 C22 107.96(15) . .
O3 S1 C22 108.16(15) . .
N1 S1 C22 108.26(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.396(4) .
C1 C2 1.411(4) .
C1 C7 1.478(4) .
C2 C3 1.388(5) .
C2 H2 0.9500 .
C3 C4 1.386(5) .
C3 H3 0.9500 .
C4 C5 1.392(5) .
C4 C21 1.465(5) .
C5 C6 1.383(5) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.349(4) .
C7 H7 0.9500 .
C8 C9 1.496(5) .
C8 C12 1.520(4) .
C9 O1 1.226(4) .
C9 C10 1.500(4) .
C10 C13 1.335(4) .
C10 C11 1.522(4) .
C11 N1 1.478(4) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 N1 1.483(4) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.474(5) .
C13 H13 0.9500 .
C14 C19 1.396(5) .
C14 C15 1.399(5) .
C15 C16 1.392(5) .
C15 H15 0.9500 .
C16 C17 1.384(5) .
C16 H16 0.9500 .
C17 C18 1.403(5) .
C17 C20 1.449(5) .
C18 C19 1.385(5) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 N3 1.138(4) .
C21 N2 1.150(5) .
C22 C27 1.393(4) .
C22 C23 1.397(4) .
C22 S1 1.766(3) .
C23 C24 1.396(5) .
C23 H23 0.9500 .
C24 C25 1.375(5) .
C24 H24 0.9500 .
C25 F1 1.364(4) .
C25 C26 1.374(5) .
C26 C27 1.393(4) .
C26 H26 0.9500 .
C27 H27 0.9500 .
N1 S1 1.647(3) .
O2 S1 1.430(2) .
O3 S1 1.436(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C26 H26 O2 0.95 2.35 3.286(5) 169.5 1_455
C11 H11B N3 0.99 2.45 3.413(5) 165.0 4_666
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
C6 C1 C2 C3 -1.9(5) . . . .
C7 C1 C2 C3 -179.5(3) . . . .
C1 C2 C3 C4 2.0(5) . . . .
C2 C3 C4 C5 -0.5(5) . . . .
C2 C3 C4 C21 179.5(3) . . . .
C3 C4 C5 C6 -1.1(5) . . . .
C21 C4 C5 C6 178.9(3) . . . .
C4 C5 C6 C1 1.2(5) . . . .
C2 C1 C6 C5 0.3(5) . . . .
C7 C1 C6 C5 177.8(3) . . . .
C6 C1 C7 C8 39.6(5) . . . .
C2 C1 C7 C8 -142.9(3) . . . .
C1 C7 C8 C9 176.8(3) . . . .
C1 C7 C8 C12 2.0(5) . . . .
C7 C8 C9 O1 5.8(5) . . . .
C12 C8 C9 O1 -179.1(3) . . . .
C7 C8 C9 C10 -171.3(3) . . . .
C12 C8 C9 C10 3.8(4) . . . .
O1 C9 C10 C13 -6.2(5) . . . .
C8 C9 C10 C13 170.9(3) . . . .
O1 C9 C10 C11 177.4(3) . . . .
C8 C9 C10 C11 -5.5(4) . . . .
C13 C10 C11 N1 -143.0(3) . . . .
C9 C10 C11 N1 33.1(4) . . . .
C7 C8 C12 N1 145.1(3) . . . .
C9 C8 C12 N1 -29.6(4) . . . .
C9 C10 C13 C14 -176.2(3) . . . .
C11 C10 C13 C14 -0.1(5) . . . .
C10 C13 C14 C19 135.2(4) . . . .
C10 C13 C14 C15 -42.7(5) . . . .
C19 C14 C15 C16 0.1(5) . . . .
C13 C14 C15 C16 178.0(3) . . . .
C14 C15 C16 C17 -0.9(5) . . . .
C15 C16 C17 C18 1.5(5) . . . .
C15 C16 C17 C20 -179.0(3) . . . .
C16 C17 C18 C19 -1.2(5) . . . .
C20 C17 C18 C19 179.2(3) . . . .
C17 C18 C19 C14 0.4(5) . . . .
C15 C14 C19 C18 0.1(5) . . . .
C13 C14 C19 C18 -177.9(3) . . . .
C27 C22 C23 C24 -2.3(5) . . . .
S1 C22 C23 C24 175.0(2) . . . .
C22 C23 C24 C25 1.0(5) . . . .
C23 C24 C25 F1 179.8(3) . . . .
C23 C24 C25 C26 0.8(5) . . . .
F1 C25 C26 C27 179.6(3) . . . .
C24 C25 C26 C27 -1.4(5) . . . .
C25 C26 C27 C22 0.0(5) . . . .
C23 C22 C27 C26 1.8(5) . . . .
S1 C22 C27 C26 -175.5(2) . . . .
C10 C11 N1 C12 -60.7(3) . . . .
C10 C11 N1 S1 85.0(3) . . . .
C8 C12 N1 C11 58.7(3) . . . .
C8 C12 N1 S1 -86.8(3) . . . .
C11 N1 S1 O2 173.1(2) . . . .
C12 N1 S1 O2 -43.9(3) . . . .
C11 N1 S1 O3 44.3(2) . . . .
C12 N1 S1 O3 -172.7(2) . . . .
C11 N1 S1 C22 -71.3(2) . . . .
C12 N1 S1 C22 71.7(3) . . . .
C27 C22 S1 O2 -153.6(3) . . . .
C23 C22 S1 O2 29.0(3) . . . .
C27 C22 S1 O3 -21.6(3) . . . .
C23 C22 S1 O3 161.0(2) . . . .
C27 C22 S1 N1 92.1(3) . . . .
C23 C22 S1 N1 -85.3(3) . . . .
