#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/21/2232106.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_2232106
loop_
_publ_author_name
'Feizbakhsh Bazargani, Mona'
'Talavat, Laleh'
'Naderi, Soheila'
'Khavasi, Hamid Reza'
_publ_section_title
;
 2-[(1H-Imidazol-2-yl)disulfanyl]-1H-imidazole
;
_journal_coeditor_code           XU5318
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2585
_journal_paper_doi               10.1107/S1600536811036014
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H6 N4 S2'
_chemical_formula_moiety         'C6 H6 N4 S2'
_chemical_formula_sum            'C6 H6 N4 S2'
_chemical_formula_weight         198.29
_chemical_name_systematic
;
2-[(1H-Imidazol-2-yl)disulfanyl]-1H-imidazole
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 122.29(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.083(3)
_cell_length_b                   6.3928(13)
_cell_length_c                   9.922(2)
_cell_measurement_reflns_used    1007
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3.42
_cell_volume                     755.1(4)
_computing_cell_refinement       'X-AREA  (Stoe & Cie, 2005)'
_computing_data_collection       'X-AREA  (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA  (Stoe & Cie, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0.15
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4116
_diffrn_reflns_theta_full        29.17
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         3.42
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(XRED and XSHAPE;  Stoe & Cie, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.564
_refine_ls_extinction_coef       0.11(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         1007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0549
_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)+(0.1134P)²+0.6898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1847
_reflns_number_gt                948
_reflns_number_total             1007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5318.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2232106
_cod_database_fobs_code          2232106
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 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
S S1 0.08686(5) 0.07449(9) 0.32168(6) 0.0337(4) Uani d . 1
N N1 0.13136(17) 0.4761(4) 0.4347(2) 0.0319(5) Uani d . 1
N N2 0.11134(18) 0.2432(4) 0.5892(2) 0.0350(6) Uani d . 1
H H2A 0.1006 0.129 0.625 0.042 Uiso calc R 1
C C1 0.11109(17) 0.2743(4) 0.4570(2) 0.0281(5) Uani d . 1
C C2 0.1440(2) 0.5734(4) 0.5611(3) 0.0335(6) Uani d . 1
H H2 0.1585 0.7155 0.5821 0.04 Uiso calc R 1
C C3 0.13289(18) 0.4382(4) 0.6536(2) 0.0280(5) Uani d . 1
H H3 0.139 0.4723 0.7491 0.034 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0385(5) 0.0326(5) 0.0294(5) 0.00531(19) 0.0178(4) -0.00166(17)
N1 0.0407(10) 0.0348(11) 0.0256(9) -0.0026(8) 0.0213(7) -0.0020(7)
N2 0.0451(11) 0.0375(11) 0.0271(10) 0.0024(8) 0.0226(8) 0.0042(7)
C1 0.0300(10) 0.0334(11) 0.0222(10) 0.0028(8) 0.0147(8) 0.0011(7)
C2 0.0382(12) 0.0369(14) 0.0260(11) -0.0032(8) 0.0175(9) -0.0040(7)
C3 0.0316(10) 0.0373(13) 0.0180(9) 0.0023(7) 0.0151(8) -0.0010(7)
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'
S S 0.1246 0.1234 '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_3
_geom_angle
C1 S1 S1 2 101.62(7)
C2 N1 C1 . 102.96(19)
C1 N2 C3 . 102.12(19)
C1 N2 H2A . 128.9
C3 N2 H2A . 128.9
N2 C1 N1 . 114.4(2)
N2 C1 S1 . 123.13(18)
N1 C1 S1 . 122.51(16)
N1 C2 C3 . 110.0(2)
N1 C2 H2 . 125
C3 C2 H2 . 125
C2 C3 N2 . 110.52(19)
C2 C3 H3 . 124.7
N2 C3 H3 . 124.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C1 . 1.750(2)
S1 S1 2 2.0713(14)
N1 C2 . 1.324(3)
N1 C1 . 1.364(3)
N2 C1 . 1.324(3)
N2 C3 . 1.359(3)
N2 H2A . 0.86
C2 C3 . 1.329(3)
C2 H2 . 0.93
C3 H3 . 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
N2 H2A S1 4_555 0.86 2.44 3.227(3) 153 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_1
_geom_torsion
C3 N2 C1 N1 . 0.1(3)
C3 N2 C1 S1 . -179.85(15)
C2 N1 C1 N2 . -0.4(3)
C2 N1 C1 S1 . 179.60(17)
S1 S1 C1 N2 2 86.31(19)
S1 S1 C1 N1 2 -93.68(18)
C1 N1 C2 C3 . 0.5(3)
N1 C2 C3 N2 . -0.4(3)
C1 N2 C3 C2 . 0.2(3)
