#------------------------------------------------------------------------------
#$Date: 2016-06-18 04:40:34 +0300 (Sat, 18 Jun 2016) $
#$Revision: 183689 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/34/1543477.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_1543477
loop_
_publ_author_name
'Abusaadiya, Salima M.'
'Yamin, Bohari M.'
'Ngatiman, Fadzlee'
'Hasbullah, Siti Aishah'
_publ_section_title
;
 1,1'-(Ethane-1,2-diyl)bis[3-(4-chlorobenzoyl)thiourea]
;
_journal_coeditor_code           SJ4038
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x160927
_journal_paper_doi               10.1107/S2414314616009275
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C18 H16 Cl2 N4 O2 S2'
_chemical_formula_moiety         'C18 H16 Cl2 N4 O2 S2'
_chemical_formula_sum            'C18 H16 Cl2 N4 O2 S2'
_chemical_formula_weight         455.37
_chemical_name_systematic
;
1,1'-(Ethane-1,2-diyl)bis[3-(4-chlorobenzoyl)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                91.030(2)
_cell_angle_beta                 91.835(2)
_cell_angle_gamma                94.878(2)
_cell_formula_units_Z            1
_cell_length_a                   6.0099(3)
_cell_length_b                   8.7905(4)
_cell_length_c                   9.2603(4)
_cell_measurement_reflns_used    20610
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      3.1
_cell_volume                     487.09(4)
_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
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector diffractometer
;
_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  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20610
_diffrn_reflns_theta_full        28.53
_diffrn_reflns_theta_max         28.53
_diffrn_reflns_theta_min         3.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  0.9451
_exptl_absorpt_correction_T_min  0.7634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             234
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.404
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0356
_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)+(0.0389P)²+0.2974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                1985
_reflns_number_total             2421
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj4038sup1.cif
_cod_data_source_block           I
_cod_database_code               1543477
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
_atom_site_symmetry_multiplicity
Cl Cl1 0.35967(9) 1.43588(6) 0.67959(5) 0.04843(16) Uani d . 1 1
S S1 0.41800(7) 0.75184(5) -0.05845(5) 0.03377(14) Uani d . 1 1
O O1 -0.1332(2) 0.92654(15) 0.20898(15) 0.0379(3) Uani d . 1 1
N N1 0.2191(2) 0.92314(16) 0.12526(16) 0.0310(3) Uani d D 1 1
H H1A 0.342(2) 0.981(2) 0.120(2) 0.035(5) Uiso d D 1 1
N N2 0.0029(2) 0.71056(16) 0.03437(17) 0.0306(3) Uani d D 1 1
H H2A -0.107(3) 0.743(3) 0.081(3) 0.059(8) Uiso d D 1 1
C C1 -0.0034(3) 1.1925(2) 0.3763(2) 0.0350(4) Uani d . 1 1
H H1 -0.1497 1.1852 0.3394 0.042 Uiso calc R 1 1
C C2 0.0614(3) 1.2974(2) 0.4854(2) 0.0377(4) Uani d . 1 1
H H2 -0.0401 1.3614 0.5215 0.045 Uiso calc R 1 1
C C3 0.2780(3) 1.3064(2) 0.54035(18) 0.0315(4) Uani d . 1 1
C C4 0.4312(3) 1.2145(2) 0.4867(2) 0.0353(4) Uani d . 1 1
H H4 0.5772 1.2221 0.5243 0.042 Uiso calc R 1 1
C C5 0.3664(3) 1.1105(2) 0.37613(19) 0.0320(4) Uani d . 1 1
H H5 0.4696 1.0488 0.3386 0.038 Uiso calc R 1 1
C C6 0.1481(3) 1.09795(18) 0.32110(17) 0.0264(3) Uani d . 1 1
C C7 0.0619(3) 0.97689(18) 0.21382(18) 0.0272(3) Uani d . 1 1
C C8 0.1979(3) 0.79277(18) 0.03623(18) 0.0263(3) Uani d . 1 1
C C9 -0.0421(3) 0.56512(18) -0.0434(2) 0.0311(4) Uani d . 1 1
H H9A 0.0307 0.5703 -0.1354 0.037 Uiso calc R 1 1
H H9B -0.2016 0.5455 -0.0626 0.037 Uiso calc R 1 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C7 N1 C8 . . 127.96(14)
C7 N1 H1A . . 115.7(14)
C8 N1 H1A . . 116.2(14)
C8 N2 C9 . . 123.80(14)
C8 N2 H2A . . 119.6(18)
C9 N2 H2A . . 116.6(18)
C2 C1 C6 . . 120.52(17)
C2 C1 H1 . . 119.7
C6 C1 H1 . . 119.7
C3 C2 C1 . . 119.29(17)
C3 C2 H2 . . 120.4
C1 C2 H2 . . 120.4
C4 C3 C2 . . 121.17(16)
C4 C3 Cl1 . . 119.23(14)
C2 C3 Cl1 . . 119.60(14)
C3 C4 C5 . . 119.38(17)
C3 C4 H4 . . 120.3
C5 C4 H4 . . 120.3
C4 C5 C6 . . 120.32(16)
C4 C5 H5 . . 119.8
C6 C5 H5 . . 119.8
C5 C6 C1 . . 119.30(16)
C5 C6 C7 . . 122.74(15)
C1 C6 C7 . . 117.72(16)
O1 C7 N1 . . 122.85(15)
O1 C7 C6 . . 121.59(15)
N1 C7 C6 . . 115.52(14)
N2 C8 N1 . . 116.65(14)
N2 C8 S1 . . 125.18(12)
N1 C8 S1 . . 118.17(12)
N2 C9 C9 . 2_565 111.15(18)
N2 C9 H9A . . 109.4
C9 C9 H9A 2_565 . 109.4
N2 C9 H9B . . 109.4
C9 C9 H9B 2_565 . 109.4
H9A C9 H9B . . 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C3 . 1.7354(17)
S1 C8 . 1.6709(17)
O1 C7 . 1.217(2)
N1 C7 . 1.378(2)
N1 C8 . 1.394(2)
N1 H1A . 0.862(9)
N2 C8 . 1.323(2)
N2 C9 . 1.456(2)
N2 H2A . 0.865(10)
C1 C2 . 1.380(3)
C1 C6 . 1.387(2)
C1 H1 . 0.9300
C2 C3 . 1.378(3)
C2 H2 . 0.9300
C3 C4 . 1.374(3)
C4 C5 . 1.384(3)
C4 H4 . 0.9300
C5 C6 . 1.386(3)
C5 H5 . 0.9300
C6 C7 . 1.491(2)
C9 C9 2_565 1.522(4)
C9 H9A . 0.9700
C9 H9B . 0.9700
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 H2A O1 1_555 0.87(2) 2.01(3) 2.670(2) 133(2) yes
C9 H9A S1 1_555 0.97 2.77 3.1017(18) 101 no
N1 H1A S1 2_675 0.864(14) 2.729(17) 3.5203(14) 153.1(13) 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_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . -0.6(3)
C1 C2 C3 C4 . 1.1(3)
C1 C2 C3 Cl1 . -179.00(15)
C2 C3 C4 C5 . -0.4(3)
Cl1 C3 C4 C5 . 179.68(14)
C3 C4 C5 C6 . -0.7(3)
C4 C5 C6 C1 . 1.1(3)
C4 C5 C6 C7 . -173.06(17)
C2 C1 C6 C5 . -0.5(3)
C2 C1 C6 C7 . 174.04(17)
C8 N1 C7 O1 . -11.3(3)
C8 N1 C7 C6 . 166.43(17)
C5 C6 C7 O1 . 149.94(18)
C1 C6 C7 O1 . -24.4(3)
C5 C6 C7 N1 . -27.9(2)
C1 C6 C7 N1 . 157.85(16)
C9 N2 C8 N1 . -174.95(16)
C9 N2 C8 S1 . 4.8(3)
C7 N1 C8 N2 . 0.8(3)
C7 N1 C8 S1 . -178.87(15)
C8 N2 C9 C9 2_565 81.7(2)

_cod_database_fobs_code 1543477
