#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/03/2230310.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_2230310
loop_
_publ_author_name
'Hübscher, Jörg'
'Izotova, Lidiya'
'Talipov, Samat'
'Katzsch, Felix'
'Weber, Edwin'
_publ_section_title
;
 S,S'-(Pyridazine-3,6-diyl)dithiouronium dichloride
 methanol monosolvate
;
_journal_coeditor_code           FJ2416
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1477
_journal_paper_doi               10.1107/S1600536811018514
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H10 N6 S2 2+, 2Cl -, C H4 O'
_chemical_formula_moiety         'C6 H10 N6 S2 2+, 2(Cl -), C H4 O'
_chemical_formula_sum            'C7 H14 Cl2 N6 O S2'
_chemical_formula_weight         333.26
_chemical_name_common
;
S,S'-(Pyridazine-3,6-diyl)dithiouronium dichloride methanol
monosolvate
;
_chemical_name_systematic
;
{Amino[(6-{[amino(iminiumyl)methyl]sulfanyl}pyridazin-3-
yl)sulfanyl]methylidene}azanium dichloride methanol monosolvate
;
_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                104.148(2)
_cell_angle_beta                 98.066(2)
_cell_angle_gamma                108.695(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7457(2)
_cell_length_b                   9.0234(3)
_cell_length_c                   13.0165(4)
_cell_measurement_reflns_used    32534
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      1.66
_cell_volume                     706.81(4)
_computing_cell_refinement       'X-AREA (Stoe &Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe &Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'sealed X-ray tube, long-fine focus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0158
_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       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3234
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.9586
_exptl_absorpt_correction_T_min  0.7386
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.331
_refine_ls_extinction_coef       0.055(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0299
_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)+(0.0481P)²+0.1092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0745
_reflns_number_gt                2765
_reflns_number_total             3234
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2416.cif
_cod_data_source_block           I
_cod_database_code               2230310
_cod_database_fobs_code          2230310
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.46287(7) 0.17255(5) 0.64021(3) 0.03256(12) Uani d . 1 1 . .
Cl Cl2 0.10144(7) 0.26455(6) 0.02016(4) 0.03622(12) Uani d . 1 1 . .
O O1G 0.5002(2) -0.10500(17) 0.13659(11) 0.0364(3) Uani d . 1 1 . .
C C1G 0.7040(4) 0.0147(3) 0.1460(2) 0.0570(6) Uani d . 1 1 . .
H H1G1 0.7251 0.1146 0.2013 0.085 Uiso calc R 1 1 . .
H H1G2 0.7098 0.0358 0.0775 0.085 Uiso calc R 1 1 . .
H H1G3 0.8152 -0.0251 0.1658 0.085 Uiso calc R 1 1 . .
H H1G 0.518(5) -0.132(4) 0.197(2) 0.059(8) Uiso d . 1 1 . .
H H4B 0.434(4) 0.053(3) 0.357(2) 0.048(7) Uiso d . 1 1 . .
H H5A 0.436(4) 0.388(3) 0.780(2) 0.037(6) Uiso d . 1 1 . .
H H6B 0.410(4) 0.684(3) 0.992(2) 0.040(6) Uiso d . 1 1 . .
H H3A 0.201(4) 0.137(3) 0.138(2) 0.046(6) Uiso d . 1 1 . .
H H4A 0.441(5) 0.205(4) 0.439(2) 0.059(8) Uiso d . 1 1 . .
H H5B 0.581(4) 0.541(3) 0.880(2) 0.047(7) Uiso d . 1 1 . .
H H3B 0.330(4) 0.032(3) 0.169(2) 0.056(8) Uiso d . 1 1 . .
H H6A 0.183(5) 0.646(3) 0.947(2) 0.049(7) Uiso d . 1 1 . .
S S1 0.22215(7) 0.35351(5) 0.32279(3) 0.02800(11) Uani d . 1 1 . .
S S2 0.02098(7) 0.37603(6) 0.77378(3) 0.03286(12) Uani d . 1 1 . .
C C4 0.0693(2) 0.36263(19) 0.64195(12) 0.0231(3) Uani d . 1 1 . .
N N1 0.2518(2) 0.48701(16) 0.53011(11) 0.0265(3) Uani d . 1 1 . .
N N2 0.2047(2) 0.49603(17) 0.62795(11) 0.0284(3) Uani d . 1 1 . .
C C3 -0.0424(3) 0.2143(2) 0.55821(13) 0.0277(3) Uani d . 1 1 . .
H H3 -0.1409 0.1249 0.5703 0.033 Uiso calc R 1 1 . .
C C1 0.1553(2) 0.34686(18) 0.44932(12) 0.0220(3) Uani d . 1 1 . .
N N6 0.2904(3) 0.6233(2) 0.93770(13) 0.0357(3) Uani d . 1 1 . .
C C6 0.2824(3) 0.50356(19) 0.85521(13) 0.0261(3) Uani d . 1 1 . .
C C2 -0.0002(3) 0.2071(2) 0.45784(13) 0.0271(3) Uani d . 1 1 . .
H H2 -0.0716 0.1135 0.3979 0.033 Uiso calc R 1 1 . .
N N3 0.2723(3) 0.1075(2) 0.18987(12) 0.0352(3) Uani d . 1 1 . .
N N5 0.4521(3) 0.4721(2) 0.83639(13) 0.0335(3) Uani d . 1 1 . .
N N4 0.3980(3) 0.1435(2) 0.37169(13) 0.0308(3) Uani d . 1 1 . .
C C5 0.3058(2) 0.18519(19) 0.29330(13) 0.0232(3) Uani d . 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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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
C1G O1G H1G . . 103.6(19) ?
O1G C1G H1G1 . . 109.5 ?
O1G C1G H1G2 . . 109.5 ?
H1G1 C1G H1G2 . . 109.5 ?
O1G C1G H1G3 . . 109.5 ?
H1G1 C1G H1G3 . . 109.5 ?
H1G2 C1G H1G3 . . 109.5 ?
C5 S1 C1 . . 100.19(7) ?
C6 S2 C4 . . 99.98(8) ?
N2 C4 C3 . . 123.90(14) ?
N2 C4 S2 . . 117.88(11) ?
C3 C4 S2 . . 118.18(12) ?
C1 N1 N2 . . 118.93(13) ?
C4 N2 N1 . . 119.05(13) ?
C2 C3 C4 . . 116.86(15) ?
C2 C3 H3 . . 121.6 ?
C4 C3 H3 . . 121.6 ?
N1 C1 C2 . . 124.05(14) ?
N1 C1 S1 . . 114.57(11) ?
C2 C1 S1 . . 121.20(12) ?
C6 N6 H6B . . 123.2(15) ?
C6 N6 H6A . . 122.6(19) ?
H6B N6 H6A . . 114(2) ?
N6 C6 N5 . . 123.12(17) ?
N6 C6 S2 . . 115.38(14) ?
N5 C6 S2 . . 121.38(13) ?
C3 C2 C1 . . 116.94(14) ?
C3 C2 H2 . . 121.5 ?
C1 C2 H2 . . 121.5 ?
C5 N3 H3A . . 120.2(16) ?
C5 N3 H3B . . 120.0(18) ?
H3A N3 H3B . . 120(2) ?
C6 N5 H5A . . 119.1(15) ?
C6 N5 H5B . . 117.8(16) ?
H5A N5 H5B . . 123(2) ?
C5 N4 H4B . . 121.2(17) ?
C5 N4 H4A . . 122(2) ?
H4B N4 H4A . . 116(3) ?
N3 C5 N4 . . 123.08(15) ?
N3 C5 S1 . . 115.75(13) ?
N4 C5 S1 . . 121.17(12) ?
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
O1G C1G . 1.417(3) ?
O1G H1G . 0.89(3) ?
C1G H1G1 . 0.9600 ?
C1G H1G2 . 0.9600 ?
C1G H1G3 . 0.9600 ?
S1 C5 . 1.7603(16) ?
S1 C1 . 1.7775(15) ?
S2 C6 . 1.7709(17) ?
S2 C4 . 1.7738(15) ?
C4 N2 . 1.329(2) ?
C4 C3 . 1.399(2) ?
N1 C1 . 1.326(2) ?
N1 N2 . 1.3450(19) ?
C3 C2 . 1.366(2) ?
C3 H3 . 0.9300 ?
C1 C2 . 1.398(2) ?
N6 C6 . 1.305(2) ?
N6 H6B . 0.90(3) ?
N6 H6A . 0.83(3) ?
C6 N5 . 1.305(2) ?
C2 H2 . 0.9300 ?
N3 C5 . 1.306(2) ?
N3 H3A . 0.92(3) ?
N3 H3B . 0.89(3) ?
N5 H5A . 0.89(2) ?
N5 H5B . 0.90(3) ?
N4 C5 . 1.315(2) ?
N4 H4B . 0.91(3) ?
N4 H4A . 0.86(3) ?
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
O1G H1G Cl1 2_656 0.89(3) 2.22(3) 3.1038(15) 171(3)
N3 H3A Cl2 . 0.92(3) 2.28(3) 3.1746(17) 166(2)
N3 H3B O1G . 0.89(3) 1.95(3) 2.839(2) 171(3)
N4 H4A Cl1 . 0.86(3) 2.70(3) 3.3950(16) 139(2)
N4 H4B Cl1 2_656 0.91(3) 2.36(3) 3.2522(15) 167(2)
N5 H5A Cl1 . 0.89(2) 2.39(2) 3.2614(16) 170(2)
N5 H5B Cl2 2_666 0.90(3) 2.25(3) 3.1413(17) 173(2)
N6 H6A Cl2 2_566 0.83(3) 2.36(3) 3.1878(19) 175(3)
N6 H6B O1G 1_566 0.90(3) 2.17(2) 2.891(2) 136(2)
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 S2 C4 N2 . . . . -37.51(14) ?
C6 S2 C4 C3 . . . . 144.58(13) ?
C3 C4 N2 N1 . . . . -5.3(2) ?
S2 C4 N2 N1 . . . . 176.96(11) ?
C1 N1 N2 C4 . . . . 2.6(2) ?
N2 C4 C3 C2 . . . . 2.9(2) ?
S2 C4 C3 C2 . . . . -179.32(13) ?
N2 N1 C1 C2 . . . . 2.3(2) ?
N2 N1 C1 S1 . . . . 177.35(11) ?
C5 S1 C1 N1 . . . . 126.26(12) ?
C5 S1 C1 C2 . . . . -58.54(14) ?
C4 S2 C6 N6 . . . . 134.58(13) ?
C4 S2 C6 N5 . . . . -49.21(15) ?
C4 C3 C2 C1 . . . . 1.9(2) ?
N1 C1 C2 C3 . . . . -4.5(2) ?
S1 C1 C2 C3 . . . . -179.24(12) ?
C1 S1 C5 N3 . . . . 149.37(13) ?
C1 S1 C5 N4 . . . . -31.32(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656698
