#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/81/2238174.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_2238174
loop_
_publ_author_name
'Bouchareb, Hasna'
'Boudraa, Mhamed'
'Bouacida, Sofiane'
'Merazig, Hocin'
_publ_section_title
;
 2,2'-(Disulfanediyl)dianilinium dichloride dihydrate
;
_journal_coeditor_code           HB7089
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1078
_journal_page_last               o1079
_journal_paper_doi               10.1107/S1600536813015742
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H14 N2 S2 2+, 2Cl -, 2H2 O'
_chemical_formula_moiety         'C12 H14 N2 S2 2+, 2(Cl -), 2(H2 O)'
_chemical_formula_sum            'C12 H18 Cl2 N2 O2 S2'
_chemical_formula_weight         357.32
_chemical_name_systematic
;
2,2'-(Disulfanediyl)dianilinium dichloride dihydrate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.826(7)
_cell_length_b                   13.358(5)
_cell_length_c                   7.120(3)
_cell_measurement_reflns_used    2698
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      2.29
_cell_volume                     1695.4(12)
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2005)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.097
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10760
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.79
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.4
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.471
_refine_ls_abs_structure_details 'Flack (1983), 1369 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.12(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.063
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0595P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                2409
_reflns_number_total             3584
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7089.cif
_cod_data_source_block           I
_cod_database_code               2238174
_cod_database_fobs_code          2238174
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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 Cl2 0.98060(6) 0.10914(8) 1.19390(17) 0.0269(3) Uani d . 1 1
S S1 0.86675(9) -0.10667(11) 1.3286(2) 0.0412(4) Uani d . 1 1
Cl Cl1 0.99242(8) 0.36455(10) 0.7389(2) 0.0411(4) Uani d . 1 1
S S2 0.85864(8) -0.15845(11) 1.0567(2) 0.0395(4) Uani d . 1 1
O O2W 0.9096(2) 0.1819(3) 1.5764(6) 0.0381(10) Uani d D 1 1
H H3W 0.935(3) 0.233(3) 1.609(9) 0.057 Uiso d D 1 1
H H4W 0.937(3) 0.150(4) 1.497(7) 0.057 Uiso d D 1 1
N N2 0.8933(2) 0.0331(3) 0.8354(6) 0.0267(9) Uani d . 1 1
H H2A 0.8991 0.0831 0.7542 0.04 Uiso calc R 1 1
H H2B 0.9208 -0.019 0.7989 0.04 Uiso calc R 1 1
H H2C 0.9082 0.0528 0.9489 0.04 Uiso calc R 1 1
C C21 0.7911(3) -0.0781(4) 0.9473(8) 0.0286(12) Uani d . 1 1
O O1W 1.0599(3) 0.4223(3) 1.3483(6) 0.0534(12) Uani d D 1 1
H H1W 1.043(4) 0.476(3) 1.302(9) 0.08 Uiso d D 1 1
H H2W 1.039(4) 0.406(4) 1.453(6) 0.08 Uiso d D 1 1
N N1 0.9146(2) -0.2839(3) 1.5749(6) 0.0282(10) Uani d . 1 1
H H1A 0.9242 -0.3284 1.6647 0.042 Uiso calc R 1 1
H H1B 0.9388 -0.2271 1.5996 0.042 Uiso calc R 1 1
H H1C 0.9298 -0.3079 1.4647 0.042 Uiso calc R 1 1
C C26 0.8140(2) 0.0039(3) 0.8427(7) 0.0218(10) Uani d . 1 1
C C14 0.7102(3) -0.3103(4) 1.6647(8) 0.0317(12) Uani d . 1 1
H H14 0.6782 -0.3509 1.7342 0.038 Uiso calc R 1 1
C C12 0.7275(3) -0.1730(4) 1.4523(8) 0.0332(13) Uani d . 1 1
H H12 0.7073 -0.1212 1.3811 0.04 Uiso calc R 1 1
C C25 0.7627(3) 0.0625(3) 0.7478(8) 0.0272(11) Uani d . 1 1
H H25 0.7787 0.1168 0.6768 0.033 Uiso calc R 1 1
C C15 0.7858(3) -0.3249(3) 1.6726(7) 0.0268(11) Uani d . 1 1
H H15 0.8055 -0.3753 1.7482 0.032 Uiso calc R 1 1
C C11 0.8050(3) -0.1876(3) 1.4566(7) 0.0255(11) Uani d . 1 1
C C23 0.6638(3) -0.0391(4) 0.8641(8) 0.0395(14) Uani d . 1 1
H H23 0.6128 -0.0526 0.8741 0.047 Uiso calc R 1 1
C C24 0.6876(3) 0.0396(4) 0.7590(8) 0.0345(12) Uani d . 1 1
H H24 0.6528 0.0784 0.6943 0.041 Uiso calc R 1 1
C C16 0.8335(3) -0.2645(3) 1.5676(7) 0.0237(10) Uani d . 1 1
C C13 0.6811(3) -0.2350(4) 1.5534(8) 0.0381(13) Uani d . 1 1
H H13 0.6294 -0.2262 1.5468 0.046 Uiso calc R 1 1
C C22 0.7156(3) -0.1002(4) 0.9572(8) 0.0354(13) Uani d . 1 1
H H22 0.6992 -0.1554 1.0255 0.043 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 0 '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 0.006 '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
C11 S1 S2 103.43(17)
C21 S2 S1 104.74(18)
H3W O2W H4W 106(6)
C26 N2 H2A 109.5
C26 N2 H2B 109.5
H2A N2 H2B 109.5
C26 N2 H2C 109.5
H2A N2 H2C 109.5
H2B N2 H2C 109.5
C22 C21 C26 118.9(5)
C22 C21 S2 120.3(4)
C26 C21 S2 120.6(4)
H1W O1W H2W 114(3)
C16 N1 H1A 109.5
C16 N1 H1B 109.5
H1A N1 H1B 109.5
C16 N1 H1C 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
C25 C26 C21 121.0(4)
C25 C26 N2 118.1(4)
C21 C26 N2 120.8(4)
C15 C14 C13 120.0(5)
C15 C14 H14 120
C13 C14 H14 120
C13 C12 C11 120.0(5)
C13 C12 H12 120
C11 C12 H12 120
C24 C25 C26 119.4(5)
C24 C25 H25 120.3
C26 C25 H25 120.3
C14 C15 C16 119.9(5)
C14 C15 H15 120
C16 C15 H15 120
C16 C11 C12 118.5(4)
C16 C11 S1 120.7(4)
C12 C11 S1 120.8(4)
C24 C23 C22 120.4(5)
C24 C23 H23 119.8
C22 C23 H23 119.8
C23 C24 C25 120.5(5)
C23 C24 H24 119.7
C25 C24 H24 119.7
C15 C16 C11 120.7(4)
C15 C16 N1 118.7(4)
C11 C16 N1 120.6(4)
C12 C13 C14 120.9(5)
C12 C13 H13 119.5
C14 C13 H13 119.5
C21 C22 C23 119.6(5)
C21 C22 H22 120.2
C23 C22 H22 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C11 1.792(5)
S1 S2 2.061(2)
S2 C21 1.791(5)
O2W H3W 0.86(2)
O2W H4W 0.86(2)
N2 C26 1.468(6)
N2 H2A 0.89
N2 H2B 0.89
N2 H2C 0.89
C21 C22 1.380(7)
C21 C26 1.386(7)
O1W H1W 0.852(19)
O1W H2W 0.858(19)
N1 C16 1.469(6)
N1 H1A 0.89
N1 H1B 0.89
N1 H1C 0.89
C26 C25 1.380(7)
C14 C15 1.364(6)
C14 C13 1.380(8)
C14 H14 0.93
C12 C13 1.375(8)
C12 C11 1.396(7)
C12 H12 0.93
C25 C24 1.375(7)
C25 H25 0.93
C15 C16 1.391(7)
C15 H15 0.93
C11 C16 1.391(7)
C23 C24 1.358(8)
C23 C22 1.399(8)
C23 H23 0.93
C24 H24 0.93
C13 H13 0.93
C22 H22 0.93
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
N1 H1A O1W 2_755 0.89 1.83 2.723(6) 178 yes
N1 H1B Cl2 2_755 0.89 2.24 3.108(4) 166 yes
N1 H1C Cl1 2_755 0.89 2.25 3.103(4) 160 yes
N2 H2A O2W 1_554 0.89 1.84 2.727(6) 177 yes
N2 H2B Cl2 2_754 0.89 2.26 3.111(4) 160 yes
N2 H2C Cl2 . 0.89 2.30 3.157(4) 163 yes
O2W H4W Cl2 . 0.86(5) 2.36(5) 3.157(5) 155(5) yes
O2W H3W Cl1 1_556 0.85(5) 2.23(5) 3.078(4) 171(6) yes
O1W H1W Cl1 2_765 0.85(5) 2.27(5) 3.096(5) 167(5) yes
O1W H2W Cl1 1_556 0.86(5) 2.27(5) 3.127(5) 176(7) 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
C11 S1 S2 C21 96.8(2)
S1 S2 C21 C22 -87.5(5)
S1 S2 C21 C26 96.2(4)
C22 C21 C26 C25 -0.7(8)
S2 C21 C26 C25 175.7(4)
C22 C21 C26 N2 177.1(4)
S2 C21 C26 N2 -6.5(6)
C21 C26 C25 C24 0.7(7)
N2 C26 C25 C24 -177.1(5)
C13 C14 C15 C16 -0.4(7)
C13 C12 C11 C16 -1.3(7)
C13 C12 C11 S1 -179.1(4)
S2 S1 C11 C16 103.3(4)
S2 S1 C11 C12 -78.8(4)
C22 C23 C24 C25 -2.1(8)
C26 C25 C24 C23 0.7(8)
C14 C15 C16 C11 1.2(7)
C14 C15 C16 N1 -178.3(4)
C12 C11 C16 C15 -0.3(7)
S1 C11 C16 C15 177.5(4)
C12 C11 C16 N1 179.1(4)
S1 C11 C16 N1 -3.0(6)
C11 C12 C13 C14 2.1(8)
C15 C14 C13 C12 -1.2(8)
C26 C21 C22 C23 -0.8(8)
S2 C21 C22 C23 -177.2(4)
C24 C23 C22 C21 2.2(9)
