#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/42/2234292.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_2234292
loop_
_publ_author_name
'Kang, Sung Kwon'
'Cho, Nam Sook'
'Jang, Siyoung'
_publ_section_title
;
 5-({3-[(5-Amino-1,3,4-thiadiazol-2-yl)sulfanylmethyl]benzyl}sulfanyl)-1,3,4-thiadiazol-2-amine
;
_journal_coeditor_code           IS5100
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1241
_journal_paper_doi               10.1107/S1600536812013116
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H12 N6 S4'
_chemical_formula_moiety         'C12 H12 N6 S4'
_chemical_formula_sum            'C12 H12 N6 S4'
_chemical_formula_weight         368.52
_chemical_name_systematic
;
5-({3-[(5-Amino-1,3,4-thiadiazol-2-yl)sulfanylmethyl]benzyl}sulfanyl)-1,3,4-
thiadiazol-2-amine
;
_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                 90.3730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3579(10)
_cell_length_b                   6.1382(4)
_cell_length_c                   30.7095(18)
_cell_measurement_reflns_used    3247
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.13
_cell_measurement_theta_min      2.49
_cell_volume                     3083.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            22777
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.62
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.346
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.883
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0280P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                2387
_reflns_number_total             3836
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            is5100.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2234292
_cod_database_fobs_code          2234292
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'
'-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
C C1 0.07088(13) 0.5674(4) 0.54356(7) 0.0349(5) Uani d . 1
C C2 0.04110(13) 0.4333(3) 0.57612(7) 0.0355(5) Uani d . 1
H H2 0.0609 0.2917 0.5784 0.043 Uiso calc R 1
C C3 -0.01744(12) 0.5042(4) 0.60545(7) 0.0354(5) Uani d . 1
C C4 -0.04693(13) 0.7144(4) 0.60143(8) 0.0427(6) Uani d . 1
H H4 -0.0857 0.7658 0.6209 0.051 Uiso calc R 1
C C5 -0.01915(14) 0.8485(4) 0.56860(8) 0.0462(6) Uani d . 1
H H5 -0.0406 0.9881 0.5657 0.055 Uiso calc R 1
C C6 0.04010(14) 0.7777(4) 0.54005(7) 0.0428(6) Uani d . 1
H H6 0.0594 0.8706 0.5185 0.051 Uiso calc R 1
C C7 0.13626(13) 0.4864(4) 0.51346(7) 0.0400(5) Uani d . 1
H H7A 0.1306 0.5602 0.4857 0.048 Uiso calc R 1
H H7B 0.128 0.332 0.5084 0.048 Uiso calc R 1
S S8 0.24002(3) 0.52863(9) 0.534089(19) 0.03947(16) Uani d . 1
C C9 0.24017(12) 0.3680(3) 0.58115(7) 0.0327(5) Uani d . 1
S S10 0.22830(4) 0.08693(9) 0.580246(18) 0.03689(15) Uani d . 1
C C11 0.24370(12) 0.0940(4) 0.63625(7) 0.0324(5) Uani d . 1
N N12 0.25717(11) 0.2911(3) 0.65155(6) 0.0376(4) Uani d . 1
N N13 0.25390(10) 0.4480(3) 0.61950(6) 0.0357(4) Uani d . 1
N N14 0.24306(11) -0.0849(3) 0.66089(6) 0.0426(5) Uani d . 1
H H14A 0.2518 -0.0752 0.6885 0.051 Uiso calc R 1
H H14B 0.2339 -0.21 0.6492 0.051 Uiso calc R 1
C C15 -0.04979(13) 0.3540(4) 0.64040(7) 0.0430(6) Uani d . 1
H H15A -0.0909 0.2599 0.6274 0.052 Uiso calc R 1
H H15B -0.0766 0.4418 0.6624 0.052 Uiso calc R 1
S S16 0.02620(4) 0.18512(10) 0.66701(2) 0.04862(18) Uani d . 1
C C17 0.07177(13) 0.3682(3) 0.70332(7) 0.0363(5) Uani d . 1
S S18 0.06869(4) 0.64865(10) 0.69824(2) 0.04757(18) Uani d . 1
C C19 0.12945(13) 0.6580(4) 0.74495(7) 0.0391(5) Uani d . 1
N N20 0.14884(12) 0.4662(3) 0.76028(6) 0.0430(5) Uani d . 1
N N21 0.11434(12) 0.2993(3) 0.73582(6) 0.0455(5) Uani d . 1
N N22 0.15219(12) 0.8447(3) 0.76364(6) 0.0564(6) Uani d . 1
H H22A 0.1812 0.8428 0.7871 0.068 Uiso calc R 1
H H22B 0.1378 0.9669 0.7522 0.068 Uiso calc R 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'
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
C2 C1 C6 118.6(2)
C2 C1 C7 120.16(19)
C6 C1 C7 121.2(2)
C1 C2 C3 121.9(2)
C1 C2 H2 119
C3 C2 H2 119
C4 C3 C2 118.4(2)
C4 C3 C15 120.6(2)
C2 C3 C15 121.0(2)
C5 C4 C3 120.3(2)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 120.8(2)
C4 C5 H5 119.6
C6 C5 H5 119.6
C5 C6 C1 119.9(2)
C5 C6 H6 120
C1 C6 H6 120
C1 C7 S8 113.78(15)
C1 C7 H7A 108.8
S8 C7 H7A 108.8
C1 C7 H7B 108.8
S8 C7 H7B 108.8
H7A C7 H7B 107.7
C9 S8 C7 101.71(10)
N13 C9 S10 114.22(16)
N13 C9 S8 122.50(16)
S10 C9 S8 123.17(12)
C9 S10 C11 86.78(10)
N12 C11 N14 123.81(19)
N12 C11 S10 113.52(16)
N14 C11 S10 122.66(17)
C11 N12 N13 112.45(17)
C9 N13 N12 113.00(17)
C11 N14 H14A 120
C11 N14 H14B 120
H14A N14 H14B 120
C3 C15 S16 115.29(15)
C3 C15 H15A 108.5
S16 C15 H15A 108.5
C3 C15 H15B 108.5
S16 C15 H15B 108.5
H15A C15 H15B 107.5
C17 S16 C15 102.05(11)
N21 C17 S18 114.41(17)
N21 C17 S16 120.73(17)
S18 C17 S16 124.80(13)
C17 S18 C19 86.69(11)
N20 C19 N22 123.6(2)
N20 C19 S18 113.79(17)
N22 C19 S18 122.63(17)
C19 N20 N21 111.92(18)
C17 N21 N20 113.17(18)
C19 N22 H22A 120
C19 N22 H22B 120
H22A N22 H22B 120
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.386(3)
C1 C6 1.390(3)
C1 C7 1.503(3)
C2 C3 1.389(3)
C2 H2 0.93
C3 C4 1.383(3)
C3 C15 1.513(3)
C4 C5 1.381(3)
C4 H4 0.93
C5 C6 1.381(3)
C5 H5 0.93
C6 H6 0.93
C7 S8 1.826(2)
C7 H7A 0.97
C7 H7B 0.97
S8 C9 1.749(2)
C9 N13 1.294(2)
C9 S10 1.737(2)
S10 C11 1.737(2)
C11 N12 1.316(3)
C11 N14 1.334(3)
N12 N13 1.378(2)
N14 H14A 0.86
N14 H14B 0.86
C15 S16 1.810(2)
C15 H15A 0.97
C15 H15B 0.97
S16 C17 1.747(2)
C17 N21 1.285(3)
C17 S18 1.729(2)
S18 C19 1.741(2)
C19 N20 1.306(3)
C19 N22 1.333(3)
N20 N21 1.388(2)
N22 H22A 0.86
N22 H22B 0.86
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
N14 H14A N20 4_546 0.86 2.27 3.005(3) 144
N14 H14B N13 1_545 0.86 2.31 3.142(2) 162
N22 H22A N12 4_556 0.86 2.15 3.007(3) 171
N22 H22B N21 1_565 0.86 2.14 2.982(3) 168
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6071108
