#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/01/2230177.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_2230177
loop_
_publ_author_name
'Tang, Jun-Mei'
'Feng, Zhi-Qiang'
'Cheng, Wei'
_publ_section_title
;
 Bis(4-amino-2-chlorophenyl) disulfide
;
_journal_coeditor_code           XU5174
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1197
_journal_paper_doi               10.1107/S1600536811014425
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H10 Cl2 N2 S2'
_chemical_formula_moiety         'C12 H10 Cl2 N2 S2'
_chemical_formula_sum            'C12 H10 Cl2 N2 S2'
_chemical_formula_weight         317.24
_chemical_name_common
;
Bis(4-amino-2-chlorophenyl) disulfide
;
_chemical_name_systematic
;
4-[(4-amino-2-chlorophenyl)disulfanyl]-3-chloroaniline
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.09(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6360(13)
_cell_length_b                   14.907(3)
_cell_length_c                   13.588(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10
_cell_volume                     1338.9(5)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2606
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.222
_refine_ls_abs_structure_details 'Flack (1983), 110 Friedel parirs'
_refine_ls_abs_structure_Flack   0.09(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1331
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0312
_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)+(0.0660P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                1221
_reflns_number_total             1331
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5174.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2230177
_cod_database_fobs_code          2230177
loop_
_symmetry_equiv_pos_as_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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.28662(15) 0.23231(7) 0.80302(8) 0.0442(3) Uani d . 1 . .
Cl Cl1 -0.1503(2) 0.18083(8) 0.87818(12) 0.0609(4) Uani d . 1 . .
N N1 -0.3017(9) 0.5116(3) 0.9000(3) 0.0681(14) Uani d . 1 . .
H H1A -0.2710 0.5674 0.8950 0.082 Uiso d R 1 . .
H H1B -0.4135 0.4965 0.9229 0.082 Uiso d R 1 . .
C C1 -0.0811(7) 0.2917(3) 0.8603(3) 0.0380(9) Uani d . 1 . .
Cl Cl2 -0.2000(2) 0.26890(7) 0.57856(11) 0.0586(4) Uani d . 1 . .
S S2 0.26156(17) 0.21357(8) 0.65170(9) 0.0441(3) Uani d . 1 . .
N N2 -0.3804(7) -0.0596(3) 0.5629(3) 0.0525(10) Uani d . 1 . .
H H2A -0.3514 -0.1157 0.5684 0.063 Uiso d R 1 . .
H H2B -0.5012 -0.0431 0.5426 0.063 Uiso d R 1 . .
C C2 -0.2194(8) 0.3561(3) 0.8835(3) 0.0431(10) Uani d . 1 . .
H H2C -0.3415 0.3397 0.9070 0.052 Uiso calc R 1 . .
C C3 -0.1716(8) 0.4459(3) 0.8708(3) 0.0453(11) Uani d . 1 . .
C C4 0.0098(8) 0.4693(3) 0.8332(3) 0.0455(11) Uani d . 1 . .
H H4A 0.0401 0.5292 0.8226 0.055 Uiso calc R 1 . .
C C5 0.1417(8) 0.4043(3) 0.8121(3) 0.0425(10) Uani d . 1 . .
H H5A 0.2634 0.4208 0.7881 0.051 Uiso calc R 1 . .
C C6 0.1012(6) 0.3126(3) 0.8252(3) 0.0358(9) Uani d . 1 . .
C C7 0.0675(7) 0.1343(3) 0.6287(3) 0.0364(9) Uani d . 1 . .
C C8 0.1075(7) 0.0430(3) 0.6402(3) 0.0418(10) Uani d . 1 . .
H H8A 0.2376 0.0250 0.6627 0.050 Uiso calc R 1 . .
C C9 -0.0379(8) -0.0212(3) 0.6193(3) 0.0464(11) Uani d . 1 . .
H H9A -0.0047 -0.0815 0.6277 0.056 Uiso calc R 1 . .
C C10 -0.2349(7) 0.0029(3) 0.5857(3) 0.0379(10) Uani d . 1 . .
C C11 -0.2776(7) 0.0940(3) 0.5730(3) 0.0371(9) Uani d . 1 . .
H H11A -0.4068 0.1122 0.5490 0.044 Uiso calc R 1 . .
C C12 -0.1295(7) 0.1569(3) 0.5957(3) 0.0377(10) 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'
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
_geom_angle_publ_flag
C6 S1 S2 . . 105.43(14) ?
C3 N1 H1A . . 120.2 ?
C3 N1 H1B . . 119.8 ?
H1A N1 H1B . . 120.0 ?
C6 C1 C2 . . 122.9(4) ?
C6 C1 Cl1 . . 121.0(3) ?
C2 C1 Cl1 . . 116.1(4) ?
C7 S2 S1 . . 105.13(15) ?
C10 N2 H2A . . 119.9 ?
C10 N2 H2B . . 120.1 ?
H2A N2 H2B . . 120.0 ?
C1 C2 C3 . . 118.5(5) ?
C1 C2 H2C . . 120.8 ?
C3 C2 H2C . . 120.8 ?
N1 C3 C2 . . 119.4(5) ?
N1 C3 C4 . . 120.6(4) ?
C2 C3 C4 . . 120.0(4) ?
C5 C4 C3 . . 119.7(4) ?
C5 C4 H4A . . 120.2 ?
C3 C4 H4A . . 120.2 ?
C4 C5 C6 . . 122.3(5) ?
C4 C5 H5A . . 118.9 ?
C6 C5 H5A . . 118.9 ?
C1 C6 C5 . . 116.6(4) ?
C1 C6 S1 . . 123.7(3) ?
C5 C6 S1 . . 119.6(4) ?
C12 C7 C8 . . 116.0(4) ?
C12 C7 S2 . . 123.4(3) ?
C8 C7 S2 . . 120.5(4) ?
C9 C8 C7 . . 122.4(4) ?
C9 C8 H8A . . 118.8 ?
C7 C8 H8A . . 118.8 ?
C8 C9 C10 . . 120.7(4) ?
C8 C9 H9A . . 119.7 ?
C10 C9 H9A . . 119.7 ?
N2 C10 C9 . . 121.7(4) ?
N2 C10 C11 . . 120.5(4) ?
C9 C10 C11 . . 117.8(4) ?
C12 C11 C10 . . 120.2(4) ?
C12 C11 H11A . . 119.9 ?
C10 C11 H11A . . 119.9 ?
C11 C12 C7 . . 122.9(4) ?
C11 C12 Cl2 . . 116.4(4) ?
C7 C12 Cl2 . . 120.7(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C6 . 1.762(4) ?
S1 S2 . 2.0671(16) ?
Cl1 C1 . 1.738(4) ?
N1 C3 . 1.387(6) ?
N1 H1A . 0.8601 ?
N1 H1B . 0.8599 ?
C1 C6 . 1.375(7) ?
C1 C2 . 1.384(6) ?
Cl2 C12 . 1.744(4) ?
S2 C7 . 1.755(4) ?
N2 C10 . 1.357(6) ?
N2 H2A . 0.8599 ?
N2 H2B . 0.8600 ?
C2 C3 . 1.390(6) ?
C2 H2C . 0.9300 ?
C3 C4 . 1.393(7) ?
C4 C5 . 1.354(7) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.407(6) ?
C5 H5A . 0.9300 ?
C7 C12 . 1.385(7) ?
C7 C8 . 1.393(6) ?
C8 C9 . 1.371(7) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.393(7) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.396(6) ?
C11 C12 . 1.374(7) ?
C11 H11A . 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
N1 H1A S1 3_455 0.86 2.80 3.611(5) 158
N2 H2A S2 3_445 0.86 2.86 3.684(5) 162
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 S1 S2 C7 . . . . -84.2(2) ?
C6 C1 C2 C3 . . . . -0.1(7) ?
Cl1 C1 C2 C3 . . . . 179.9(4) ?
C1 C2 C3 N1 . . . . -175.6(4) ?
C1 C2 C3 C4 . . . . 1.6(7) ?
N1 C3 C4 C5 . . . . 175.0(4) ?
C2 C3 C4 C5 . . . . -2.1(7) ?
C3 C4 C5 C6 . . . . 1.1(6) ?
C2 C1 C6 C5 . . . . -0.8(6) ?
Cl1 C1 C6 C5 . . . . 179.2(3) ?
C2 C1 C6 S1 . . . . 175.6(3) ?
Cl1 C1 C6 S1 . . . . -4.4(5) ?
C4 C5 C6 C1 . . . . 0.3(6) ?
C4 C5 C6 S1 . . . . -176.3(3) ?
S2 S1 C6 C1 . . . . 102.4(3) ?
S2 S1 C6 C5 . . . . -81.3(3) ?
S1 S2 C7 C12 . . . . 99.7(4) ?
S1 S2 C7 C8 . . . . -82.5(3) ?
C12 C7 C8 C9 . . . . 0.6(6) ?
S2 C7 C8 C9 . . . . -177.4(3) ?
C7 C8 C9 C10 . . . . -0.2(6) ?
C8 C9 C10 N2 . . . . 178.8(4) ?
C8 C9 C10 C11 . . . . 0.8(6) ?
N2 C10 C11 C12 . . . . -179.7(4) ?
C9 C10 C11 C12 . . . . -1.7(6) ?
C10 C11 C12 C7 . . . . 2.1(6) ?
C10 C11 C12 Cl2 . . . . -179.2(3) ?
C8 C7 C12 C11 . . . . -1.5(6) ?
S2 C7 C12 C11 . . . . 176.4(3) ?
C8 C7 C12 Cl2 . . . . 179.8(3) ?
S2 C7 C12 Cl2 . . . . -2.2(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9733509
