#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/19/2211927.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_2211927
loop_
_publ_author_name
'Yusof, M. Sukeri M.'
'Edris, Mustaqim M.'
'Mardi, A. Sahali'
'Yamin, Bohari M.'
_publ_section_title
;
 N-(2-Chlorobenzoyl)-N'-(4-nitrophenyl)thiourea
;
_journal_coeditor_code           SA2028
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o94
_journal_page_last               o95
_journal_paper_doi               10.1107/S1600536806050999
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H10 Cl N3 O3 S'
_chemical_formula_moiety         'C14 H10 Cl N3 O3 S'
_chemical_formula_sum            'C14 H10 Cl N3 O3 S'
_chemical_formula_weight         335.76
_chemical_name_systematic
;
N-(2-Chlorobenzoyl)-N'-(4-nitrophenyl)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                90.045(4)
_cell_angle_beta                 100.432(4)
_cell_angle_gamma                102.271(4)
_cell_formula_units_Z            2
_cell_length_a                   5.9832(13)
_cell_length_b                   9.783(2)
_cell_length_c                   13.274(3)
_cell_measurement_reflns_used    769
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      1.5
_cell_volume                     746.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7979
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         1.5
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.8528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.040
_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)+(0.0476P)²+0.1293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.093
_refine_ls_wR_factor_ref         0.100
_reflns_number_gt                2370
_reflns_number_total             3071
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sa2028.cif
_cod_data_source_block           I
_cod_original_cell_volume        746.0(3)
_cod_database_code               2211927
_cod_database_fobs_code          2211927
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 0.72579(11) 0.08384(7) 1.15598(5) 0.0762(2) Uani d . 1
S S1 0.16990(9) 0.48591(5) 0.88731(4) 0.04373(16) Uani d . 1
O O1 0.1952(2) 0.08815(13) 1.06311(11) 0.0515(4) Uani d . 1
O O2 -0.7608(3) 0.1026(2) 0.49674(14) 0.0866(6) Uani d . 1
O O3 -0.8554(4) 0.2774(3) 0.56108(15) 0.1001(7) Uani d . 1
N N1 0.2812(3) 0.32025(15) 1.03491(11) 0.0390(4) Uani d . 1
H H1 0.3771 0.3964 1.0594 0.047 Uiso calc R 1
N N2 -0.0193(3) 0.21679(15) 0.90583(11) 0.0386(4) Uani d . 1
H H2 -0.0112 0.1401 0.9365 0.046 Uiso calc R 1
N N3 -0.7352(3) 0.1920(2) 0.56406(14) 0.0618(5) Uani d . 1
C C1 0.3672(4) 0.3332(2) 1.26062(15) 0.0517(5) Uani d . 1
H H1A 0.2382 0.3707 1.2365 0.062 Uiso calc R 1
C C2 0.4908(5) 0.3675(3) 1.35959(18) 0.0689(7) Uani d . 1
H H2A 0.4434 0.4270 1.4021 0.083 Uiso calc R 1
C C3 0.6821(5) 0.3136(3) 1.39445(19) 0.0764(8) Uani d . 1
H H3 0.7644 0.3368 1.4608 0.092 Uiso calc R 1
C C4 0.7540(4) 0.2261(3) 1.33320(19) 0.0666(7) Uani d . 1
H H4 0.8856 0.1909 1.3574 0.080 Uiso calc R 1
C C5 0.6303(3) 0.1900(2) 1.23477(16) 0.0496(5) Uani d . 1
C C6 0.4359(3) 0.24336(19) 1.19801(14) 0.0393(4) Uani d . 1
C C7 0.2945(3) 0.20572(19) 1.09275(14) 0.0368(4) Uani d . 1
C C8 0.1361(3) 0.33207(18) 0.94260(13) 0.0354(4) Uani d . 1
C C9 -0.1992(3) 0.21274(18) 0.81823(13) 0.0368(4) Uani d . 1
C C10 -0.2092(4) 0.1260(2) 0.73498(15) 0.0460(5) Uani d . 1
H H10 -0.0972 0.0730 0.7353 0.055 Uiso calc R 1
C C11 -0.3864(4) 0.1182(2) 0.65102(15) 0.0506(5) Uani d . 1
H H11 -0.3960 0.0600 0.5943 0.061 Uiso calc R 1
C C12 -0.5472(3) 0.1982(2) 0.65344(14) 0.0440(5) Uani d . 1
C C13 -0.5411(3) 0.2845(2) 0.73576(16) 0.0485(5) Uani d . 1
H H13 -0.6533 0.3375 0.7352 0.058 Uiso calc R 1
C C14 -0.3648(3) 0.2909(2) 0.81934(15) 0.0458(5) Uani d . 1
H H14 -0.3577 0.3479 0.8764 0.055 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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C8 129.66(15) yes
C7 N1 H1 115.2 ?
C8 N1 H1 115.2 ?
C8 N2 C9 123.80(15) ?
C8 N2 H2 118.1 ?
C9 N2 H2 118.1 ?
O3 N3 O2 123.4(2) ?
O3 N3 C12 118.0(2) ?
O2 N3 C12 118.7(2) ?
C6 C1 C2 120.0(2) ?
C6 C1 H1A 120.0 ?
C2 C1 H1A 120.0 ?
C3 C2 C1 119.9(2) ?
C3 C2 H2A 120.1 ?
C1 C2 H2A 120.1 ?
C4 C3 C2 120.9(2) ?
C4 C3 H3 119.6 ?
C2 C3 H3 119.6 ?
C3 C4 C5 119.7(2) ?
C3 C4 H4 120.2 ?
C5 C4 H4 120.2 ?
C6 C5 C4 120.4(2) ?
C6 C5 Cl1 119.85(16) ?
C4 C5 Cl1 119.74(18) ?
C1 C6 C5 119.20(18) ?
C1 C6 C7 118.50(17) ?
C5 C6 C7 122.29(19) ?
O1 C7 N1 123.33(17) ?
O1 C7 C6 124.03(16) ?
N1 C7 C6 112.58(15) ?
N2 C8 N1 115.92(15) yes
N2 C8 S1 125.60(14) yes
N1 C8 S1 118.47(13) yes
C14 C9 C10 120.84(17) ?
C14 C9 N2 119.92(16) ?
C10 C9 N2 119.19(17) ?
C9 C10 C11 119.70(19) ?
C9 C10 H10 120.1 ?
C11 C10 H10 120.1 ?
C12 C11 C10 118.35(19) ?
C12 C11 H11 120.8 ?
C10 C11 H11 120.8 ?
C11 C12 C13 122.85(18) ?
C11 C12 N3 118.89(19) ?
C13 C12 N3 118.26(19) ?
C12 C13 C14 118.37(18) ?
C12 C13 H13 120.8 ?
C14 C13 H13 120.8 ?
C9 C14 C13 119.88(18) ?
C9 C14 H14 120.1 ?
C13 C14 H14 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C5 1.722(2) ?
S1 C8 1.6646(18) yes
O1 C7 1.206(2) yes
O2 N3 1.216(3) ?
O3 N3 1.209(3) ?
N1 C7 1.367(2) ?
N1 C8 1.388(2) yes
N1 H1 0.8600 ?
N2 C8 1.328(2) yes
N2 C9 1.429(2) ?
N2 H2 0.8600 ?
N3 C12 1.471(2) ?
C1 C6 1.381(3) ?
C1 C2 1.388(3) ?
C1 H1A 0.9300 ?
C2 C3 1.367(4) ?
C2 H2A 0.9300 ?
C3 C4 1.364(4) ?
C3 H3 0.9300 ?
C4 C5 1.385(3) ?
C4 H4 0.9300 ?
C5 C6 1.384(3) ?
C6 C7 1.497(3) ?
C9 C14 1.376(3) ?
C9 C10 1.377(3) ?
C10 C11 1.382(3) ?
C10 H10 0.9300 ?
C11 C12 1.368(3) ?
C11 H11 0.9300 ?
C12 C13 1.371(3) ?
C13 C14 1.377(3) ?
C13 H13 0.9300 ?
C14 H14 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
_geom_hbond_publ_flag
N2 H2 O1 1_555 0.86 2.03 2.704(2) 134 yes
N1 H1 S1 2_667 0.86 2.67 3.4014(19) 143 yes
N2 H2 O1 2_557 0.86 2.27 3.000(2) 143 yes
C3 H3 O3 1_756 0.93 2.60 3.298(4) 132 yes
C11 H11 O2 2_456 0.93 2.43 3.274(3) 151 yes
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 0.8(4)
C1 C2 C3 C4 0.0(4)
C2 C3 C4 C5 -0.8(4)
C3 C4 C5 C6 0.7(3)
C3 C4 C5 Cl1 178.03(19)
C2 C1 C6 C5 -0.9(3)
C2 C1 C6 C7 178.35(19)
C4 C5 C6 C1 0.1(3)
Cl1 C5 C6 C1 -177.22(15)
C4 C5 C6 C7 -179.09(19)
Cl1 C5 C6 C7 3.6(3)
C8 N1 C7 O1 10.2(3)
C8 N1 C7 C6 -167.08(18)
C1 C6 C7 O1 -118.4(2)
C5 C6 C7 O1 60.8(3)
C1 C6 C7 N1 58.8(2)
C5 C6 C7 N1 -122.0(2)
C9 N2 C8 N1 172.83(16)
C9 N2 C8 S1 -7.5(3)
C7 N1 C8 N2 2.6(3)
C7 N1 C8 S1 -177.16(15)
C8 N2 C9 C14 -61.6(3)
C8 N2 C9 C10 120.9(2)
C14 C9 C10 C11 0.6(3)
N2 C9 C10 C11 178.13(18)
C9 C10 C11 C12 0.2(3)
C10 C11 C12 C13 -0.6(3)
C10 C11 C12 N3 179.31(19)
O3 N3 C12 C11 -169.6(2)
O2 N3 C12 C11 9.8(3)
O3 N3 C12 C13 10.3(3)
O2 N3 C12 C13 -170.3(2)
C11 C12 C13 C14 0.1(3)
N3 C12 C13 C14 -179.75(19)
C10 C9 C14 C13 -1.1(3)
N2 C9 C14 C13 -178.55(18)
C12 C13 C14 C9 0.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3126892
