#------------------------------------------------------------------------------
#$Date: 2017-01-29 15:00:33 +0200 (Sun, 29 Jan 2017) $
#$Revision: 191062 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/05/4510565.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_4510565
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_absolute_configuration ad
_chemical_formula_moiety         'C7 H6 N2 O2 S'
_chemical_formula_sum            'C7 H6 N2 O2 S'
_chemical_formula_weight         182.20
_chemical_name_common            2-nitro-thiobenzamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.077(7)
_cell_length_b                   12.808(10)
_cell_length_c                   7.145(4)
_cell_measurement_reflns_used    4031
_cell_measurement_temperature    300.(2)
_cell_measurement_theta_max      24.9779
_cell_measurement_theta_min      2.7392
_cell_volume                     830.7(10)
_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      300(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6935
_diffrn_reflns_theta_full        25.47
_diffrn_reflns_theta_max         25.47
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.208
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1511
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0753P)²+0.0729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                1398
_reflns_number_total             1511
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401891f_si_003.cif
_cod_data_source_block           Compound_11
_cod_depositor_comments
;
 Correcting a typo in the data item name by changing it from
 '_geom_torsion_atm_site_label_1' to '_geom_torsion_atom_site_label_1'.

 Antanas Vaitkus,
 2017-01-29

 Adding full bibliography for 4510565--4510578.cif.
;
_cod_database_code               4510565
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'
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 0.1046(3) 0.34663(18) 0.2431(4) 0.0334(5) Uani d . 1
C C2 0.2076(3) 0.42493(19) 0.2080(4) 0.0369(5) Uani d . 1
C C3 0.3134(3) 0.4527(2) 0.3354(5) 0.0511(7) Uani d . 1
H H3 0.382 0.5041 0.306 0.061 Uiso calc R 1
C C4 0.3173(3) 0.4043(3) 0.5067(4) 0.0548(8) Uani d . 1
H H4 0.3874 0.4238 0.595 0.066 Uiso calc R 1
C C5 0.2185(4) 0.3276(3) 0.5471(5) 0.0586(8) Uani d . 1
H H5 0.2223 0.2943 0.6627 0.07 Uiso calc R 1
C C6 0.1124(4) 0.2988(2) 0.4180(4) 0.0482(7) Uani d . 1
H H6 0.0452 0.2466 0.4484 0.058 Uiso calc R 1
C C7 -0.0129(3) 0.3090(2) 0.1121(4) 0.0356(6) Uani d . 1
N N10 0.2061(3) 0.48004(18) 0.0283(4) 0.0513(6) Uani d . 1
O O12 0.3094(3) 0.5362(2) -0.0098(5) 0.1018(12) Uani d . 1
S S8 0.02100(7) 0.21113(5) -0.03514(13) 0.0502(2) Uani d . 1
N N9 -0.1413(3) 0.3519(2) 0.1332(4) 0.0499(6) Uani d D 1
O O11 0.1034(3) 0.46824(19) -0.0766(3) 0.0673(7) Uani d . 1
H H9A -0.218(4) 0.321(4) 0.096(10) 0.119(19) Uiso d D 1
H H9B -0.159(4) 0.402(3) 0.207(5) 0.072(12) Uiso d D 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'
O O 0.0106 0.0060 '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 116.4(2)
C6 C1 C7 117.0(2)
C2 C1 C7 126.6(2)
C3 C2 C1 122.5(3)
C3 C2 N10 117.6(2)
C1 C2 N10 119.9(2)
C2 C3 C4 119.6(3)
C2 C3 H3 120.2
C4 C3 H3 120.2
C5 C4 C3 119.9(3)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 120.6(3)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 121.0(3)
C5 C6 H6 119.5
C1 C6 H6 119.5
N9 C7 C1 115.5(2)
N9 C7 S8 124.0(2)
C1 C7 S8 120.35(19)
O11 N10 O12 122.2(3)
O11 N10 C2 119.4(2)
O12 N10 C2 118.4(3)
C7 N9 H9A 121.(4)
C7 N9 H9B 125.(3)
H9A N9 H9B 113.(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.393(4)
C1 C2 1.394(4)
C1 C7 1.499(3)
C2 C3 1.370(4)
C2 N10 1.465(4)
C3 C4 1.373(5)
C3 H3 0.93
C4 C5 1.361(5)
C4 H4 0.93
C5 C6 1.384(5)
C5 H5 0.93
C6 H6 0.93
C7 N9 1.297(4)
C7 S8 1.665(3)
N10 O11 1.205(4)
N10 O12 1.213(4)
N9 H9A 0.85(2)
N9 H9B 0.845(19)
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 3_455 0.85(2) 2.58(3) 3.391(3) 162.(5)
N9 H9B O11 2_565 0.845(19) 2.33(2) 3.118(4) 156.(3)
N9 H9B O12 2_565 0.845(19) 2.56(3) 3.299(5) 146.(4)
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 1.3(4)
C7 C1 C2 C3 -178.6(3)
C6 C1 C2 N10 -179.3(2)
C7 C1 C2 N10 0.7(4)
C1 C2 C3 C4 -1.7(4)
N10 C2 C3 C4 179.0(3)
C2 C3 C4 C5 1.4(5)
C3 C4 C5 C6 -0.9(5)
C4 C5 C6 C1 0.5(5)
C2 C1 C6 C5 -0.7(4)
C7 C1 C6 C5 179.2(3)
C6 C1 C7 N9 85.2(3)
C2 C1 C7 N9 -94.9(3)
C6 C1 C7 S8 -89.7(3)
C2 C1 C7 S8 90.2(3)
C3 C2 N10 O11 -169.9(3)
C1 C2 N10 O11 10.8(4)
C3 C2 N10 O12 10.3(4)
C1 C2 N10 O12 -169.1(3)
