#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/39/2233901.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_2233901
loop_
_publ_author_name
'Kang, Sung Kwon'
'Cho, Nam Sook'
'Jang, Siyoung'
_publ_section_title
;
 5,5'-[1,4-Phenylenebis(methylenesulfanediyl)]bis[1,3,4-thiadiazol-2(3H)-one]
 dimethyl sulfoxide disolvate
;
_journal_coeditor_code           IS5071
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o781
_journal_paper_doi               10.1107/S1600536812006289
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H10 N4 O2 S4 , 2C2 H6 O S'
_chemical_formula_moiety         'C12 H10 N4 O2 S4, 2(C2 H6 O S)'
_chemical_formula_sum            'C16 H22 N4 O4 S6'
_chemical_formula_weight         526.74
_chemical_name_common
;
5,5'-[1,4-Phenylenebis(methylenesulfanediyl)]bis[1,3,4-thiadiazol-
2(3H)-one] dimethyl sulfoxide disolvate
;
_chemical_name_systematic
;
5-({4-[(5-oxo-4,5-dihydro-1,3,4-thiadiazol-2-yl)methyl]phenyl}methyl)-
2,3-dihydro-1,3,4-thiadiazol-2-one dimethyl sulfoxide disolvate
;
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                109.70(4)
_cell_angle_beta                 95.74(3)
_cell_angle_gamma                91.15(3)
_cell_formula_units_Z            1
_cell_length_a                   7.5723(15)
_cell_length_b                   8.3258(17)
_cell_length_c                   10.346(2)
_cell_measurement_reflns_used    5678
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      2.6
_cell_volume                     610.0(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21342
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.1
_exptl_absorpt_coefficient_mu    0.59
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         3039
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.05
_refine_ls_R_factor_gt           0.0337
_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)+(0.0506P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                2124
_reflns_number_total             3039
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5071.cif
_cod_data_source_block           I
_cod_original_cell_volume        610.0(2)
_cod_database_code               2233901
_cod_database_fobs_code          2233901
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_disorder_assembly
_atom_site_disorder_group
S S1 0.76776(6) 0.37928(6) 0.42321(5) 0.07516(18) Uani d . 1 . .
C C2 0.7758(2) 0.3744(2) 0.59474(19) 0.0668(4) Uani d . 1 . .
N N3 0.62432(19) 0.2937(2) 0.60130(16) 0.0688(4) Uani d . 1 . .
H H3 0.589(3) 0.282(3) 0.679(2) 0.090(7) Uiso d . 1 . .
N N4 0.50062(17) 0.23800(17) 0.48623(14) 0.0611(3) Uani d . 1 . .
C C5 0.55873(19) 0.27358(19) 0.38640(17) 0.0549(4) Uani d . 1 . .
O O6 0.89774(16) 0.43193(18) 0.68683(15) 0.0946(5) Uani d . 1 . .
S S7 0.44211(6) 0.22149(6) 0.22259(5) 0.06970(16) Uani d . 1 . .
C C8 0.2421(2) 0.1210(2) 0.25284(16) 0.0598(4) Uani d . 1 . .
H H8A 0.2729 0.0257 0.283 0.072 Uiso calc R 1 . .
H H8B 0.1848 0.2027 0.3249 0.072 Uiso calc R 1 . .
C C9 0.11735(19) 0.05870(19) 0.12143(15) 0.0516(3) Uani d . 1 . .
C C10 -0.0134(2) 0.1597(2) 0.09349(16) 0.0610(4) Uani d . 1 . .
H H10 -0.0228 0.2687 0.1563 0.073 Uiso calc R 1 . .
C C11 0.1302(2) -0.1018(2) 0.02588(16) 0.0603(4) Uani d . 1 . .
H H11 0.2181 -0.1713 0.0421 0.072 Uiso calc R 1 . .
S S12 0.32235(7) 0.21416(7) 0.85488(5) 0.0693(2) Uani d P 0.8786(14) A 1
O O13 0.5091(2) 0.2414(3) 0.8277(2) 0.0771(6) Uani d P 0.8786(14) A 1
C C14 0.1951(5) 0.1372(4) 0.6870(4) 0.0807(9) Uani d P 0.8786(14) A 1
H H14A 0.2232 0.0218 0.639 0.121 Uiso calc PR 0.8786(14) A 1
H H14B 0.2238 0.2084 0.635 0.121 Uiso calc PR 0.8786(14) A 1
H H14C 0.0706 0.1402 0.6975 0.121 Uiso calc PR 0.8786(14) A 1
C C15 0.2328(6) 0.4158(6) 0.9137(4) 0.0964(12) Uani d P 0.8786(14) A 1
H H15A 0.2907 0.4803 1.0039 0.145 Uiso calc PR 0.8786(14) A 1
H H15B 0.1078 0.4017 0.9183 0.145 Uiso calc PR 0.8786(14) A 1
H H15C 0.2511 0.4757 0.8509 0.145 Uiso calc PR 0.8786(14) A 1
S S12A 0.3220(5) 0.3284(5) 0.7826(4) 0.0717(14) Uani d PD 0.1214(14) A 2
O O13A 0.5108(17) 0.3036(17) 0.8234(16) 0.057(4) Uiso d PD 0.1214(14) A 2
C C14A 0.209(5) 0.126(3) 0.729(3) 0.093(11) Uiso d PD 0.1214(14) A 2
H H14D 0.29 0.0394 0.6939 0.14 Uiso calc PR 0.1214(14) A 2
H H14E 0.1146 0.1194 0.6573 0.14 Uiso calc PR 0.1214(14) A 2
H H14F 0.1595 0.1102 0.8058 0.14 Uiso calc PR 0.1214(14) A 2
C C15A 0.250(5) 0.410(5) 0.952(2) 0.087(10) Uiso d PD 0.1214(14) A 2
H H15D 0.3501 0.4642 1.0183 0.13 Uiso calc PR 0.1214(14) A 2
H H15E 0.1998 0.3176 0.9746 0.13 Uiso calc PR 0.1214(14) A 2
H H15F 0.1623 0.4918 0.953 0.13 Uiso calc PR 0.1214(14) A 2
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'
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
C5 S1 C2 . 88.75(8)
O6 C2 N3 . 127.16(19)
O6 C2 S1 . 126.18(16)
N3 C2 S1 . 106.66(12)
C2 N3 N4 . 119.02(16)
C2 N3 H3 . 125.3(14)
N4 N3 H3 . 115.3(14)
C5 N4 N3 . 109.97(14)
N4 C5 S1 . 115.59(12)
N4 C5 S7 . 123.92(12)
S1 C5 S7 . 120.48(10)
C5 S7 C8 . 98.72(8)
C9 C8 S7 . 109.26(12)
C9 C8 H8A . 109.8
S7 C8 H8A . 109.8
C9 C8 H8B . 109.8
S7 C8 H8B . 109.8
H8A C8 H8B . 108.3
C11 C9 C10 . 118.39(13)
C11 C9 C8 . 120.59(14)
C10 C9 C8 . 121.02(14)
C11 C10 C9 2 121.18(14)
C11 C10 H10 2 119.4
C9 C10 H10 . 119.4
C10 C11 C9 2 120.43(14)
C10 C11 H11 2 119.8
C9 C11 H11 . 119.8
O13 S12 C15 . 107.4(2)
O13 S12 C14 . 105.18(15)
C15 S12 C14 . 97.27(19)
S12 C14 H14A . 109.5
S12 C14 H14B . 109.5
H14A C14 H14B . 109.5
S12 C14 H14C . 109.5
H14A C14 H14C . 109.5
H14B C14 H14C . 109.5
S12 C15 H15A . 109.5
S12 C15 H15B . 109.5
H15A C15 H15B . 109.5
S12 C15 H15C . 109.5
H15A C15 H15C . 109.5
H15B C15 H15C . 109.5
O13A S12A C14A . 106.7(13)
O13A S12A C15A . 98.7(13)
C14A S12A C15A . 97.6(18)
S12A C14A H14D . 109.5
S12A C14A H14E . 109.5
H14D C14A H14E . 109.5
S12A C14A H14F . 109.5
H14D C14A H14F . 109.5
H14E C14A H14F . 109.5
S12A C15A H15D . 109.5
S12A C15A H15E . 109.5
H15D C15A H15E . 109.5
S12A C15A H15F . 109.5
H15D C15A H15F . 109.5
H15E C15A H15F . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C5 . 1.7385(16)
S1 C2 . 1.784(2)
C2 O6 . 1.220(2)
C2 N3 . 1.337(2)
N3 N4 . 1.3772(18)
N3 H3 . 0.91(2)
N4 C5 . 1.281(2)
C5 S7 . 1.7406(17)
S7 C8 . 1.8202(17)
C8 C9 . 1.502(2)
C8 H8A . 0.97
C8 H8B . 0.97
C9 C11 . 1.380(2)
C9 C10 . 1.382(2)
C10 C11 2 1.379(2)
C10 H10 . 0.93
C11 C10 2 1.379(2)
C11 H11 . 0.93
S12 O13 . 1.4964(19)
S12 C15 . 1.757(4)
S12 C14 . 1.802(4)
C14 H14A . 0.96
C14 H14B . 0.96
C14 H14C . 0.96
C15 H15A . 0.96
C15 H15B . 0.96
C15 H15C . 0.96
S12A O13A . 1.488(13)
S12A C14A . 1.758(18)
S12A C15A . 1.796(18)
C14A H14D . 0.96
C14A H14E . 0.96
C14A H14F . 0.96
C15A H15D . 0.96
C15A H15E . 0.96
C15A H15F . 0.96
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3 O13 0.91(2) 1.83(2) 2.742(3) 175.6(19)
