#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/91/2219154.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2219154
loop_
_publ_author_name
'Chai, Lan-Qin'
'Ding, Yu-Jie'
'Yang, Xiao-Qing'
'Yan, Hai-Bo'
'Dong, Wen-Kui'
_publ_section_title
;
 N-(2-Chlorobenzoyl)-N'-(3-pyridyl)thiourea
;
_journal_coeditor_code           RZ2227
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1407
_journal_paper_doi               10.1107/S1600536808019922
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H10 Cl N3 O S'
_chemical_formula_moiety         'C13 H10 Cl N3 O S'
_chemical_formula_sum            'C13 H10 Cl N3 O S'
_chemical_formula_weight         291.75
_chemical_name_systematic
;
N-(2-Chlorobenzoyl)-N'-(3-pyridyl)thiourea
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.336(4)
_cell_angle_beta                 110.797(4)
_cell_angle_gamma                112.532(4)
_cell_formula_units_Z            2
_cell_length_a                   8.421(3)
_cell_length_b                   9.282(4)
_cell_length_c                   10.512(4)
_cell_measurement_reflns_used    1514
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.635
_cell_measurement_theta_min      2.513
_cell_volume                     670.9(5)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3504
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.434
_exptl_absorpt_correction_T_max  0.9719
_exptl_absorpt_correction_T_min  0.8735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0365
_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)+(0.044P)²+0.2146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                1734
_reflns_number_total             2319
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2227.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2219154
_cod_database_fobs_code          2219154
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl Cl1 0.41414(14) 0.64074(11) 0.50918(8) 0.0781(3) Uani d . 1
N N1 0.4306(3) 0.5361(2) 0.1841(2) 0.0397(5) Uani d . 1
H H1 0.3077 0.4966 0.1477 0.048 Uiso calc R 1
N N2 0.6871(3) 0.4903(2) 0.2029(2) 0.0416(5) Uani d . 1
H H2 0.7561 0.5927 0.2548 0.050 Uiso calc R 1
N N3 1.0366(3) 0.3871(2) 0.1394(2) 0.0481(5) Uani d . 1
O O1 0.7112(3) 0.7734(2) 0.3311(2) 0.0630(5) Uani d . 1
S S1 0.33789(9) 0.24252(8) 0.02568(7) 0.0500(2) Uani d . 1
C C1 0.4967(3) 0.4294(3) 0.1432(2) 0.0370(5) Uani d . 1
C C2 0.5364(4) 0.6956(3) 0.2748(3) 0.0422(6) Uani d . 1
C C3 0.4139(3) 0.7708(3) 0.2962(2) 0.0400(5) Uani d . 1
C C4 0.3540(4) 0.7557(3) 0.4027(3) 0.0476(6) Uani d . 1
C C5 0.2449(4) 0.8281(3) 0.4233(3) 0.0560(7) Uani d . 1
H H5 0.2062 0.8177 0.4955 0.067 Uiso calc R 1
C C6 0.1944(4) 0.9154(3) 0.3359(3) 0.0613(8) Uani d . 1
H H6 0.1211 0.9644 0.3490 0.074 Uiso calc R 1
C C7 0.2513(4) 0.9307(3) 0.2296(3) 0.0593(7) Uani d . 1
H H7 0.2157 0.9895 0.1705 0.071 Uiso calc R 1
C C8 0.3611(4) 0.8595(3) 0.2093(3) 0.0495(6) Uani d . 1
H H8 0.3997 0.8711 0.1371 0.059 Uiso calc R 1
C C9 0.9299(3) 0.4610(3) 0.1477(2) 0.0411(6) Uani d . 1
H H9 0.9551 0.5586 0.1259 0.049 Uiso calc R 1
C C10 0.7848(3) 0.3985(3) 0.1872(2) 0.0380(5) Uani d . 1
C C11 0.7442(4) 0.2524(3) 0.2178(3) 0.0481(6) Uani d . 1
H H11 0.6456 0.2070 0.2436 0.058 Uiso calc R 1
C C12 0.8523(4) 0.1757(3) 0.2093(3) 0.0542(7) Uani d . 1
H H12 0.8291 0.0776 0.2300 0.065 Uiso calc R 1
C C13 0.9953(4) 0.2463(3) 0.1697(3) 0.0537(7) Uani d . 1
H H13 1.0674 0.1930 0.1636 0.064 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 N1 C1 128.3(2)
C2 N1 H1 115.9
C1 N1 H1 115.9
C1 N2 C10 124.83(19)
C1 N2 H2 117.6
C10 N2 H2 117.6
C13 N3 C9 117.2(2)
N2 C1 N1 115.4(2)
N2 C1 S1 125.54(17)
N1 C1 S1 119.02(17)
O1 C2 N1 124.8(2)
O1 C2 C3 122.1(2)
N1 C2 C3 113.1(2)
C4 C3 C8 118.6(2)
C4 C3 C2 121.6(2)
C8 C3 C2 119.8(2)
C5 C4 C3 121.1(2)
C5 C4 Cl1 119.9(2)
C3 C4 Cl1 118.97(18)
C6 C5 C4 119.2(2)
C6 C5 H5 120.4
C4 C5 H5 120.4
C7 C6 C5 120.4(2)
C7 C6 H6 119.8
C5 C6 H6 119.8
C6 C7 C8 120.5(2)
C6 C7 H7 119.7
C8 C7 H7 119.7
C7 C8 C3 120.1(2)
C7 C8 H8 119.9
C3 C8 H8 119.9
N3 C9 C10 122.6(2)
N3 C9 H9 118.7
C10 C9 H9 118.7
C9 C10 C11 119.2(2)
C9 C10 N2 119.10(19)
C11 C10 N2 121.6(2)
C12 C11 C10 118.6(2)
C12 C11 H11 120.7
C10 C11 H11 120.7
C11 C12 C13 118.8(2)
C11 C12 H12 120.6
C13 C12 H12 120.6
N3 C13 C12 123.6(2)
N3 C13 H13 118.2
C12 C13 H13 118.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.734(2)
N1 C2 1.368(3)
N1 C1 1.394(3)
N1 H1 0.8600
N2 C1 1.331(3)
N2 C10 1.422(3)
N2 H2 0.8600
N3 C13 1.335(3)
N3 C9 1.340(3)
O1 C2 1.217(3)
S1 C1 1.659(2)
C2 C3 1.508(3)
C3 C4 1.385(3)
C3 C8 1.386(3)
C4 C5 1.384(3)
C5 C6 1.372(4)
C5 H5 0.9300
C6 C7 1.369(4)
C6 H6 0.9300
C7 C8 1.380(4)
C7 H7 0.9300
C8 H8 0.9300
C9 C10 1.375(3)
C9 H9 0.9300
C10 C11 1.381(3)
C11 C12 1.371(3)
C11 H11 0.9300
C12 C13 1.373(3)
C12 H12 0.9300
C13 H13 0.9300
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
N2 H2 O1 . 0.86 1.98 2.671(3) 136.8
N1 H1 N3 1_455 0.86 2.08 2.886(4) 156.9
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
C10 N2 C1 N1 173.77(19)
C10 N2 C1 S1 -7.1(3)
C2 N1 C1 N2 1.6(3)
C2 N1 C1 S1 -177.58(18)
C1 N1 C2 O1 3.2(4)
C1 N1 C2 C3 -178.6(2)
O1 C2 C3 C4 -93.6(3)
N1 C2 C3 C4 88.1(3)
O1 C2 C3 C8 85.4(3)
N1 C2 C3 C8 -92.8(3)
C8 C3 C4 C5 -0.4(4)
C2 C3 C4 C5 178.7(2)
C8 C3 C4 Cl1 178.40(18)
C2 C3 C4 Cl1 -2.5(3)
C3 C4 C5 C6 0.4(4)
Cl1 C4 C5 C6 -178.4(2)
C4 C5 C6 C7 0.0(4)
C5 C6 C7 C8 -0.4(4)
C6 C7 C8 C3 0.4(4)
C4 C3 C8 C7 0.0(4)
C2 C3 C8 C7 -179.1(2)
C13 N3 C9 C10 0.8(4)
N3 C9 C10 C11 -1.0(4)
N3 C9 C10 N2 175.7(2)
C1 N2 C10 C9 129.9(2)
C1 N2 C10 C11 -53.4(3)
C9 C10 C11 C12 0.8(4)
N2 C10 C11 C12 -175.8(2)
C10 C11 C12 C13 -0.5(4)
C9 N3 C13 C12 -0.5(4)
C11 C12 C13 N3 0.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 769267
