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#$Date: 2022-11-22 12:12:31 +0200 (Tue, 22 Nov 2022) $
#$Revision: 279460 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106197.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_8106197
loop_
_publ_author_name
'Yeo, Chien Ing'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of the (E)-O-methyl-N-phenyl-thiocarbamate --
 4,4′-bipyridine (1/1), C18H17N3OS
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              503
_journal_page_last               505
_journal_paper_doi               10.1515/ncrs-2017-0401
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C10 H8 N2, C8 H9 N O S'
_chemical_formula_sum            'C18 H17 N3 O S'
_chemical_formula_weight         323.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 107.202(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.4754(3)
_cell_length_b                   13.8997(3)
_cell_length_c                   18.0300(4)
_cell_measurement_reflns_used    3309
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.2591
_cell_measurement_theta_min      4.6781
_cell_volume                     3226.03(13)
_computing_cell_refinement       'CrysAlis PRO [1]'
_computing_data_collection       'CrysAlis PRO [1]'
_computing_data_reduction        'CrysAlis PRO [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2014/7 [3]'
_computing_structure_refinement  'SHELXL-2014/7 [3]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6551
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        74.988
_diffrn_reflns_theta_max         74.988
_diffrn_reflns_theta_min         4.682
_exptl_absorpt_coefficient_mu    1.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis PRO [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0403P)²+2.5527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2972
_reflns_number_total             3285
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0401_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               8106197
_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   0.666
_shelx_estimated_absorpt_t_max   0.930
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
S1 S 0.67921(3) 1.01618(2) 0.31033(2) 0.02535(11) Uani 1 1 d . . . . .
O1 O 0.66639(8) 0.87788(7) 0.40900(5) 0.0211(2) Uani 1 1 d . . . . .
N1 N 0.65785(9) 0.82439(8) 0.29330(7) 0.0188(2) Uani 1 1 d . . . . .
H1N H 0.6581(13) 0.7693(14) 0.3162(10) 0.024(4) Uiso 1 1 d . . . . .
C1 C 0.66688(10) 0.90365(10) 0.33706(8) 0.0186(3) Uani 1 1 d . . . . .
C2 C 0.65421(10) 0.82017(9) 0.21395(8) 0.0179(3) Uani 1 1 d . . . . .
C3 C 0.70866(11) 0.74577(10) 0.19136(8) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.7498 0.7029 0.2292 0.024 Uiso 1 1 calc R U . . .
C4 C 0.70268(11) 0.73438(10) 0.11340(8) 0.0215(3) Uani 1 1 d . . . . .
H4 H 0.7393 0.6834 0.0980 0.026 Uiso 1 1 calc R U . . .
C5 C 0.64337(11) 0.79728(10) 0.05817(8) 0.0225(3) Uani 1 1 d . . . . .
H5 H 0.6400 0.7901 0.0051 0.027 Uiso 1 1 calc R U . . .
C6 C 0.58893(11) 0.87097(10) 0.08097(8) 0.0220(3) Uani 1 1 d . . . . .
H6 H 0.5481 0.9138 0.0431 0.026 Uiso 1 1 calc R U . . .
C7 C 0.59355(10) 0.88269(10) 0.15838(8) 0.0199(3) Uani 1 1 d . . . . .
H7 H 0.5557 0.9329 0.1734 0.024 Uiso 1 1 calc R U . . .
C8 C 0.67688(13) 0.95279(11) 0.46615(8) 0.0265(3) Uani 1 1 d . . . . .
H8A H 0.6668 0.9255 0.5135 0.040 Uiso 1 1 calc R U . . .
H8B H 0.6246 1.0027 0.4456 0.040 Uiso 1 1 calc R U . . .
H8C H 0.7464 0.9811 0.4782 0.040 Uiso 1 1 calc R U . . .
N2 N 0.62886(9) 0.63529(9) 0.34710(7) 0.0216(2) Uani 1 1 d . . . . .
N3 N 0.40921(9) 0.18236(9) 0.39977(7) 0.0253(3) Uani 1 1 d . . . . .
C9 C 0.67538(11) 0.55211(10) 0.33986(8) 0.0218(3) Uani 1 1 d . . . . .
H9 H 0.7391 0.5546 0.3274 0.026 Uiso 1 1 calc R U . . .
C10 C 0.63555(11) 0.46253(10) 0.34956(8) 0.0204(3) Uani 1 1 d . . . . .
H10 H 0.6719 0.4057 0.3441 0.025 Uiso 1 1 calc R U . . .
C11 C 0.54178(10) 0.45626(10) 0.36740(8) 0.0189(3) Uani 1 1 d . . . . .
C12 C 0.49238(11) 0.54286(11) 0.37386(9) 0.0252(3) Uani 1 1 d . . . . .
H12 H 0.4278 0.5426 0.3851 0.030 Uiso 1 1 calc R U . . .
C13 C 0.53828(11) 0.62903(10) 0.36371(9) 0.0251(3) Uani 1 1 d . . . . .
H13 H 0.5037 0.6871 0.3688 0.030 Uiso 1 1 calc R U . . .
C14 C 0.49654(10) 0.36184(10) 0.37897(8) 0.0193(3) Uani 1 1 d . . . . .
C15 C 0.52092(11) 0.27751(10) 0.34610(8) 0.0212(3) Uani 1 1 d . . . . .
H15 H 0.5684 0.2792 0.3163 0.025 Uiso 1 1 calc R U . . .
C16 C 0.47558(11) 0.19112(10) 0.35717(8) 0.0237(3) Uani 1 1 d . . . . .
H16 H 0.4924 0.1350 0.3333 0.028 Uiso 1 1 calc R U . . .
C17 C 0.38787(12) 0.26308(11) 0.43226(9) 0.0270(3) Uani 1 1 d . . . . .
H17 H 0.3422 0.2587 0.4635 0.032 Uiso 1 1 calc R U . . .
C18 C 0.42801(11) 0.35302(11) 0.42343(9) 0.0242(3) Uani 1 1 d . . . . .
H18 H 0.4090 0.4080 0.4474 0.029 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C1 O1 C8 117.94(11) . .
C1 N1 C2 126.74(12) . .
C1 N1 H1N 117.3(11) . .
C2 N1 H1N 115.9(11) . .
N1 C1 O1 108.84(11) . .
N1 C1 S1 127.13(10) . .
O1 C1 S1 124.02(10) . .
C7 C2 C3 119.93(12) . .
C7 C2 N1 122.51(12) . .
C3 C2 N1 117.41(12) . .
C4 C3 C2 119.99(13) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
C5 C4 C3 120.13(13) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 119.62(13) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C7 C6 C5 120.85(13) . .
C7 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C6 C7 C2 119.48(13) . .
C6 C7 H7 120.3 . .
C2 C7 H7 120.3 . .
O1 C8 H8A 109.5 . .
O1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
O1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C9 N2 C13 116.62(12) . .
C17 N3 C16 116.10(13) . .
N2 C9 C10 123.55(13) . .
N2 C9 H9 118.2 . .
C10 C9 H9 118.2 . .
C9 C10 C11 119.70(13) . .
C9 C10 H10 120.2 . .
C11 C10 H10 120.2 . .
C10 C11 C12 116.84(13) . .
C10 C11 C14 121.59(12) . .
C12 C11 C14 121.56(12) . .
C13 C12 C11 119.46(13) . .
C13 C12 H12 120.3 . .
C11 C12 H12 120.3 . .
N2 C13 C12 123.82(13) . .
N2 C13 H13 118.1 . .
C12 C13 H13 118.1 . .
C15 C14 C18 116.67(13) . .
C15 C14 C11 121.58(12) . .
C18 C14 C11 121.75(13) . .
C16 C15 C14 119.77(13) . .
C16 C15 H15 120.1 . .
C14 C15 H15 120.1 . .
N3 C16 C15 123.74(14) . .
N3 C16 H16 118.1 . .
C15 C16 H16 118.1 . .
N3 C17 C18 124.31(14) . .
N3 C17 H17 117.8 . .
C18 C17 H17 117.8 . .
C17 C18 C14 119.40(14) . .
C17 C18 H18 120.3 . .
C14 C18 H18 120.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.6595(14) .
O1 C1 1.3476(16) .
O1 C8 1.4420(16) .
N1 C1 1.3395(17) .
N1 C2 1.4181(17) .
N1 H1N 0.869(19) .
C2 C7 1.3938(19) .
C2 C3 1.3966(19) .
C3 C4 1.3929(19) .
C3 H3 0.9500 .
C4 C5 1.387(2) .
C4 H4 0.9500 .
C5 C6 1.391(2) .
C5 H5 0.9500 .
C6 C7 1.3881(19) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
N2 C9 1.3398(18) .
N2 C13 1.3429(18) .
N3 C17 1.336(2) .
N3 C16 1.3457(19) .
C9 C10 1.3872(19) .
C9 H9 0.9500 .
C10 C11 1.3959(19) .
C10 H10 0.9500 .
C11 C12 1.3970(19) .
C11 C14 1.4875(19) .
C12 C13 1.385(2) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.3958(19) .
C14 C18 1.3958(19) .
C15 C16 1.388(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 C18 1.390(2) .
C17 H17 0.9500 .
C18 H18 0.9500 .
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
N1 H1N N2 0.869(19) 2.016(19) 2.8681(17) 166.2(16) .
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
C2 N1 C1 O1 179.37(12) . . . .
C2 N1 C1 S1 -1.8(2) . . . .
C8 O1 C1 N1 179.12(12) . . . .
C8 O1 C1 S1 0.21(17) . . . .
C1 N1 C2 C7 -44.9(2) . . . .
C1 N1 C2 C3 139.55(14) . . . .
C7 C2 C3 C4 0.3(2) . . . .
N1 C2 C3 C4 176.00(12) . . . .
C2 C3 C4 C5 0.5(2) . . . .
C3 C4 C5 C6 -0.8(2) . . . .
C4 C5 C6 C7 0.3(2) . . . .
C5 C6 C7 C2 0.5(2) . . . .
C3 C2 C7 C6 -0.8(2) . . . .
N1 C2 C7 C6 -176.27(12) . . . .
C13 N2 C9 C10 -0.9(2) . . . .
N2 C9 C10 C11 0.4(2) . . . .
C9 C10 C11 C12 0.5(2) . . . .
C9 C10 C11 C14 -179.48(13) . . . .
C10 C11 C12 C13 -1.0(2) . . . .
C14 C11 C12 C13 179.05(13) . . . .
C9 N2 C13 C12 0.4(2) . . . .
C11 C12 C13 N2 0.5(2) . . . .
C10 C11 C14 C15 -24.1(2) . . . .
C12 C11 C14 C15 155.92(14) . . . .
C10 C11 C14 C18 155.67(14) . . . .
C12 C11 C14 C18 -24.4(2) . . . .
C18 C14 C15 C16 1.4(2) . . . .
C11 C14 C15 C16 -178.85(12) . . . .
C17 N3 C16 C15 0.0(2) . . . .
C14 C15 C16 N3 -1.3(2) . . . .
C16 N3 C17 C18 1.2(2) . . . .
N3 C17 C18 C14 -1.0(2) . . . .
C15 C14 C18 C17 -0.4(2) . . . .
C11 C14 C18 C17 179.89(13) . . . .
