#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/91/2239117.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_2239117
loop_
_publ_author_name
'Yamin, Bohari M.'
'Soh, Siti K. C.'
'Yusoff, Siti Fairus M.'
_publ_section_title
;
 N-(2-Chloro-5-nitrophenyl)-N'-(3-chloropropionyl)thiourea
;
_journal_coeditor_code           FJ2651
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o34
_journal_paper_doi               10.1107/S1600536813032662
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C10 H9 Cl2 N3 O3 S'
_chemical_formula_moiety         'C10 H9 Cl2 N3 O3 S'
_chemical_formula_sum            'C10 H9 Cl2 N3 O3 S'
_chemical_formula_weight         322.16
_chemical_name_systematic
;
N-(2-Chloro-5-nitrophenyl)-N'-(3-chloropropionyl)thiourea
;
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 106.388(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.764(6)
_cell_length_b                   5.2284(13)
_cell_length_c                   24.134(6)
_cell_measurement_temperature    298(2)
_cell_volume                     2634.7(12)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       '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  0.0193
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12266
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.759
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.9187
_exptl_absorpt_correction_T_min  0.9021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0496P)²+1.9444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                2116
_reflns_number_total             2460
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2651sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        2634.6(12)
_cod_database_code               2239117
_cod_database_fobs_code          2239117
#BEGIN Tags that were not found in dictionaries:
_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   0.788
_shelx_estimated_absorpt_t_max   0.842
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
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_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_occupancy
Cl Cl1 0.01680(3) 0.29301(14) -0.16862(3) 0.0761(2) Uani d 1
Cl Cl2 0.05486(3) 1.21922(11) -0.00637(3) 0.05899(18) Uani d 1
S S1 0.23748(3) 0.45825(11) 0.07394(2) 0.05376(18) Uani d 1
O O1 0.09544(9) 0.7795(4) -0.08527(7) 0.0804(6) Uani d 1
O O2 0.20313(12) 0.6949(5) 0.24336(8) 0.0984(7) Uani d 1
O O3 0.15801(11) 1.0096(4) 0.27253(8) 0.0953(7) Uani d 1
N N1 0.17678(8) 0.5279(3) -0.03529(7) 0.0463(4) Uani d 1
H H1 0.2031 0.4119 -0.0396 0.056 Uiso calc 1
N N2 0.14400(8) 0.7943(3) 0.02607(7) 0.0493(4) Uani d 1
H H2 0.1213 0.8542 -0.0064 0.059 Uiso calc 1
N N3 0.17078(11) 0.8880(5) 0.23452(9) 0.0698(6) Uani d 1
C C1 0.07531(12) 0.4940(5) -0.18585(9) 0.0621(6) Uani d 1
H H1A 0.0817 0.4399 -0.2223 0.075 Uiso calc 1
H H1B 0.0599 0.6690 -0.1902 0.075 Uiso calc 1
C C2 0.13788(11) 0.4820(5) -0.13939(9) 0.0643(6) Uani d 1
H H2A 0.1709 0.5636 -0.1531 0.077 Uiso calc 1
H H2B 0.1499 0.3045 -0.1310 0.077 Uiso calc 1
C C3 0.13382(11) 0.6119(5) -0.08498(9) 0.0549(5) Uani d 1
C C4 0.18352(9) 0.6053(4) 0.02127(8) 0.0423(4) Uani d 1
C C5 0.13280(9) 0.9128(4) 0.07449(8) 0.0446(4) Uani d 1
C C6 0.15981(10) 0.8404(4) 0.13142(9) 0.0522(5) Uani d 1
H H6 0.1885 0.7046 0.1404 0.063 Uiso calc 1
C C7 0.14349(11) 0.9724(4) 0.17438(9) 0.0542(5) Uani d 1
C C8 0.10111(12) 1.1733(5) 0.16383(11) 0.0633(6) Uani d 1
H H8 0.0910 1.2581 0.1940 0.076 Uiso calc 1
C C9 0.07415(11) 1.2451(5) 0.10774(11) 0.0623(6) Uani d 1
H H9 0.0452 1.3802 0.0994 0.075 Uiso calc 1
C C10 0.08968(9) 1.1184(4) 0.06386(9) 0.0488(5) Uani 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'
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
C3 N1 C4 128.54(18)
C3 N1 H1 115.7
C4 N1 H1 115.7
C4 N2 C5 131.77(17)
C4 N2 H2 114.1
C5 N2 H2 114.1
O3 N3 O2 123.3(2)
O3 N3 C7 118.3(2)
O2 N3 C7 118.3(2)
C2 C1 Cl1 110.94(17)
C2 C1 H1A 109.5
Cl1 C1 H1A 109.5
C2 C1 H1B 109.5
Cl1 C1 H1B 109.5
H1A C1 H1B 108.0
C1 C2 C3 111.67(19)
C1 C2 H2A 109.3
C3 C2 H2A 109.3
C1 C2 H2B 109.3
C3 C2 H2B 109.3
H2A C2 H2B 107.9
O1 C3 N1 122.5(2)
O1 C3 C2 122.22(19)
N1 C3 C2 115.24(19)
N2 C4 N1 114.09(17)
N2 C4 S1 127.65(15)
N1 C4 S1 118.27(15)
C6 C5 C10 117.74(19)
C6 C5 N2 125.45(19)
C10 C5 N2 116.79(18)
C7 C6 C5 118.9(2)
C7 C6 H6 120.5
C5 C6 H6 120.5
C6 C7 C8 123.2(2)
C6 C7 N3 118.4(2)
C8 C7 N3 118.4(2)
C9 C8 C7 118.1(2)
C9 C8 H8 120.9
C7 C8 H8 120.9
C8 C9 C10 120.1(2)
C8 C9 H9 119.9
C10 C9 H9 119.9
C9 C10 C5 121.8(2)
C9 C10 Cl2 118.31(18)
C5 C10 Cl2 119.85(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.788(3)
Cl2 C10 1.732(2)
S1 C4 1.656(2)
O1 C3 1.209(3)
O2 N3 1.215(3)
O3 N3 1.211(3)
N1 C3 1.368(3)
N1 C4 1.391(2)
N1 H1 0.8600
N2 C4 1.336(3)
N2 C5 1.403(2)
N2 H2 0.8600
N3 C7 1.472(3)
C1 C2 1.501(3)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.503(3)
C2 H2A 0.9700
C2 H2B 0.9700
C5 C6 1.386(3)
C5 C10 1.402(3)
C6 C7 1.373(3)
C6 H6 0.9300
C7 C8 1.373(3)
C8 C9 1.367(3)
C8 H8 0.9300
C9 C10 1.370(3)
C9 H9 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 1_555 0.86 1.87 2.596(2) 142
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
Cl1 C1 C2 C3 -70.4(3)
C4 N1 C3 O1 2.2(4)
C4 N1 C3 C2 -178.1(2)
C1 C2 C3 O1 -25.3(4)
C1 C2 C3 N1 155.0(2)
C5 N2 C4 N1 175.19(19)
C5 N2 C4 S1 -4.5(3)
C3 N1 C4 N2 -3.1(3)
C3 N1 C4 S1 176.60(18)
C4 N2 C5 C6 -4.7(3)
C4 N2 C5 C10 176.6(2)
C10 C5 C6 C7 -0.2(3)
N2 C5 C6 C7 -178.95(19)
C5 C6 C7 C8 0.4(3)
C5 C6 C7 N3 177.91(19)
O3 N3 C7 C6 177.6(2)
O2 N3 C7 C6 -4.9(3)
O3 N3 C7 C8 -4.8(3)
O2 N3 C7 C8 172.7(2)
C6 C7 C8 C9 -0.2(4)
N3 C7 C8 C9 -177.7(2)
C7 C8 C9 C10 -0.2(4)
C8 C9 C10 C5 0.4(3)
C8 C9 C10 Cl2 -179.30(18)
C6 C5 C10 C9 -0.2(3)
N2 C5 C10 C9 178.68(19)
C6 C5 C10 Cl2 179.49(15)
N2 C5 C10 Cl2 -1.7(2)
