#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/05/4510578.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_4510578
loop_
_publ_author_name
'Eccles, Kevin S.'
'Morrison, Robin E.'
'Maguire, Anita R.'
'Lawrence, Simon E.'
_publ_section_title
;
 Crystal Landscape of Primary Aromatic Thioamides
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2753
_journal_paper_doi               10.1021/cg401891f
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C8 H9 N S'
_chemical_formula_sum            'C8 H9 N S'
_chemical_formula_weight         151.22
_chemical_name_common            2-methyl-thiobenzamide
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.413(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2614(11)
_cell_length_b                   11.0313(18)
_cell_length_c                   9.6234(15)
_cell_measurement_reflns_used    4899
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.4304
_cell_measurement_theta_min      2.8160
_cell_volume                     767.4(2)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2009, 3, 0, 0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Mercury 3.0 (Macrae et al, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       'φ & ω  scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8474
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Colourless
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.317
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0272
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0369P)²+0.4680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                1438
_reflns_number_total             1572
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401891f_si_002.cif
_cod_data_source_block           Compound_10
_cod_depositor_comments
'Adding full bibliography for 4510565--4510578.cif.'
_cod_database_code               4510578
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.88735(18) 0.14733(12) 0.10536(13) 0.0134(3) Uani d . 1
C C2 0.83730(18) 0.06219(12) 0.20361(14) 0.0142(3) Uani d . 1
C C3 0.97024(19) 0.03133(12) 0.31258(14) 0.0163(3) Uani d . 1
H H3 0.9395 -0.0261 0.3802 0.02 Uiso calc R 1
C C4 1.14586(19) 0.08221(12) 0.32468(14) 0.0174(3) Uani d . 1
H H4 1.2323 0.061 0.4011 0.021 Uiso calc R 1
C C5 1.19512(18) 0.16422(13) 0.22494(15) 0.0179(3) Uani d . 1
H H5 1.3156 0.1986 0.2321 0.022 Uiso calc R 1
C C6 1.06647(19) 0.19537(12) 0.11488(14) 0.0163(3) Uani d . 1
H H6 1.1004 0.2499 0.0452 0.02 Uiso calc R 1
C C7 0.75115(18) 0.19411(12) -0.00861(14) 0.0144(3) Uani d . 1
S S8 0.58745(5) 0.29288(3) 0.02639(3) 0.01879(13) Uani d . 1
H H9A 0.708(3) 0.1814(17) -0.208(2) 0.032(5) Uiso d . 1
H H9B 0.863(3) 0.1045(17) -0.1478(18) 0.022(4) Uiso d . 1
N N9 0.77546(18) 0.15573(12) -0.13545(12) 0.0184(3) Uani d . 1
C C10 0.65014(19) 0.00187(13) 0.19246(15) 0.0200(3) Uani d . 1
H H10A 0.6532 -0.0709 0.1344 0.03 Uiso calc R 1
H H10B 0.5568 0.0582 0.1499 0.03 Uiso calc R 1
H H10C 0.6188 -0.0208 0.2858 0.03 Uiso calc R 1
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'
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
C6 C1 C2 120.47(12)
C6 C1 C7 117.58(12)
C2 C1 C7 121.90(12)
C3 C2 C1 117.60(12)
C3 C2 C10 119.98(12)
C1 C2 C10 122.40(12)
C4 C3 C2 121.88(13)
C4 C3 H3 119.1
C2 C3 H3 119.1
C3 C4 C5 119.96(12)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 119.31(12)
C6 C5 H5 120.3
C4 C5 H5 120.3
C5 C6 C1 120.71(13)
C5 C6 H6 119.6
C1 C6 H6 119.6
N9 C7 C1 115.49(12)
N9 C7 S8 123.77(11)
C1 C7 S8 120.69(10)
C7 N9 H9A 121.9(13)
C7 N9 H9B 120.0(12)
H9A N9 H9B 118.1(17)
C2 C10 H10A 109.5
C2 C10 H10B 109.5
H10A C10 H10B 109.5
C2 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3995(19)
C1 C2 1.4047(18)
C1 C7 1.4975(18)
C2 C3 1.3987(19)
C2 C10 1.5079(18)
C3 C4 1.3881(19)
C3 H3 0.95
C4 C5 1.390(2)
C4 H4 0.95
C5 C6 1.388(2)
C5 H5 0.95
C6 H6 0.95
C7 N9 1.3194(18)
C7 S8 1.6702(14)
N9 H9A 0.86(2)
N9 H9B 0.864(19)
C10 H10A 0.98
C10 H10B 0.98
C10 H10C 0.98
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N9 H9A S8 4_565 0.86(2) 2.64(2) 3.4550(13) 158.6(17)
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
C6 C1 C2 C3 2.24(19)
C7 C1 C2 C3 -175.02(12)
C6 C1 C2 C10 -175.95(12)
C7 C1 C2 C10 6.8(2)
C1 C2 C3 C4 0.0(2)
C10 C2 C3 C4 178.25(12)
C2 C3 C4 C5 -1.5(2)
C3 C4 C5 C6 0.8(2)
C4 C5 C6 C1 1.5(2)
C2 C1 C6 C5 -3.0(2)
C7 C1 C6 C5 174.33(12)
C6 C1 C7 N9 73.91(16)
C2 C1 C7 N9 -108.76(15)
C6 C1 C7 S8 -103.52(13)
C2 C1 C7 S8 73.81(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 816810
