#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/93/2019322.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_2019322
loop_
_publ_author_name
'Wu, De-Hong'
_publ_section_title
;
 Three-dimensional hydrogen-bonded assembly in
 2,2'-disulfanylidene-5,5'-biimidazolidinylidene-4,4'-dione--dimethylformamide--water
 (3/2/4)
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1545
_journal_page_last               1548
_journal_paper_doi               10.1107/S0108270113031521
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '3C6 H4 N4 O2 S2, 2C3 H7 N O, 4H2 O'
_chemical_formula_moiety         '3(C6 H4 N4 O2 S2), 2(C3 H7 N O), 4(H2 O)'
_chemical_formula_sum            'C24 H34 N14 O12 S6'
_chemical_formula_weight         903.01
_chemical_name_systematic
'2,2'-Disulfanylidene-5,5'-biimidazolidinylidene-4,4'-dione--dimethylformamide--water (3/2/4)'
_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                105.600(10)
_cell_angle_beta                 103.470(10)
_cell_angle_gamma                102.81(2)
_cell_formula_units_Z            1
_cell_length_a                   8.0655(16)
_cell_length_b                   10.391(2)
_cell_length_c                   12.735(3)
_cell_measurement_reflns_used    8524
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      3.18
_cell_volume                     952.5(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9925
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.9179
_exptl_absorpt_correction_T_min  0.9026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4359
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0421
_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)+(0.0464P)²+0.4062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                3164
_reflns_number_total             4359
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            wq3050.cif
_cod_data_source_block           I
_cod_original_cell_volume        952.5(3)
_cod_database_code               2019322
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
C C1 0.4184(3) 0.2934(2) 0.41471(16) 0.0289(4) Uani d . 1 1 . .
C C2 0.6914(3) 0.2880(2) 0.39488(16) 0.0310(4) Uani d . 1 1 . .
C C3 0.7072(3) 0.3421(2) 0.51797(16) 0.0289(4) Uani d . 1 1 . .
C C4 0.8596(3) 0.3828(2) 0.60573(16) 0.0294(4) Uani d . 1 1 . .
C C5 0.8822(3) 0.4365(2) 0.72936(16) 0.0312(4) Uani d . 1 1 . .
C C6 1.1511(3) 0.4299(2) 0.70438(17) 0.0302(4) Uani d . 1 1 . .
C C7 0.6343(3) 0.9291(2) 0.35311(17) 0.0306(4) Uani d . 1 1 . .
C C8 0.9043(3) 0.9142(2) 0.33321(17) 0.0324(5) Uani d . 1 1 . .
C C9 0.9241(3) 0.9789(2) 0.45587(16) 0.0305(4) Uani d . 1 1 . .
C C10 0.7671(3) -0.0194(3) 0.90246(18) 0.0392(5) Uani d . 1 1 . .
H H10A 0.8067 -0.0208 0.8393 0.047 Uiso calc R 1 1 . .
C C11 0.9646(4) 0.2181(3) 0.9900(2) 0.0567(7) Uani d . 1 1 . .
H H11A 0.9924 0.1952 0.9193 0.085 Uiso calc R 1 1 . .
H H11B 1.0719 0.2457 1.0533 0.085 Uiso calc R 1 1 . .
H H11C 0.9136 0.2940 0.9962 0.085 Uiso calc R 1 1 . .
C C12 0.7797(4) 0.1109(3) 1.0936(2) 0.0677(9) Uani d . 1 1 . .
H H12A 0.6957 0.0240 1.0845 0.102 Uiso calc R 1 1 . .
H H12B 0.7238 0.1839 1.1039 0.102 Uiso calc R 1 1 . .
H H12C 0.8817 0.1343 1.1596 0.102 Uiso calc R 1 1 . .
N N1 0.5383(2) 0.34206(18) 0.52230(14) 0.0316(4) Uani d . 1 1 . .
H H1A 0.5119 0.3691 0.5846 0.038 Uiso calc R 1 1 . .
N N2 0.5133(2) 0.26329(19) 0.33965(15) 0.0316(4) Uani d . 1 1 . .
N N3 1.0600(2) 0.46253(19) 0.78212(15) 0.0331(4) Uani d . 1 1 . .
N N4 1.0288(2) 0.38197(19) 0.59895(15) 0.0322(4) Uani d . 1 1 . .
N N5 0.7559(2) 0.98398(19) 0.46006(15) 0.0328(4) Uani d . 1 1 . .
N N6 0.7271(2) 0.8921(2) 0.27791(16) 0.0346(4) Uani d . 1 1 . .
N N7 0.8369(2) 0.0963(2) 0.99199(15) 0.0405(5) Uani d . 1 1 . .
O O1 0.8073(2) 0.26955(19) 0.35280(12) 0.0460(4) Uani d . 1 1 . .
O O2 0.76758(19) 0.45526(17) 0.77458(12) 0.0420(4) Uani d . 1 1 . .
O O3 1.0169(2) 0.88547(18) 0.29070(13) 0.0454(4) Uani d . 1 1 . .
O O4 0.6535(2) -0.12680(18) 0.89406(13) 0.0489(4) Uani d . 1 1 . .
O O5 0.7311(2) 0.4853(2) 0.99285(14) 0.0437(4) Uani d D 1 1 . .
O O6 0.4087(3) 0.2772(2) 0.95776(15) 0.0455(4) Uani d D 1 1 . .
S S1 0.20223(7) 0.27339(6) 0.37913(5) 0.03975(16) Uani d . 1 1 . .
S S2 0.41841(7) 0.90828(7) 0.31867(5) 0.04311(16) Uani d . 1 1 . .
S S3 1.36683(7) 0.44883(7) 0.73832(5) 0.03996(16) Uani d . 1 1 . .
H H2A 0.471(3) 0.228(2) 0.273(2) 0.034(6) Uiso d . 1 1 . .
H H3A 1.108(3) 0.484(3) 0.856(2) 0.055(8) Uiso d . 1 1 . .
H H4A 1.052(3) 0.359(2) 0.5431(18) 0.020(5) Uiso d . 1 1 . .
H H5A 0.731(3) 1.016(2) 0.518(2) 0.042(7) Uiso d . 1 1 . .
H H6A 0.683(3) 0.847(2) 0.210(2) 0.037(7) Uiso d . 1 1 . .
H H5B 0.746(4) 0.476(3) 0.9328(17) 0.059(9) Uiso d D 1 1 . .
H H6B 0.401(5) 0.236(3) 1.002(3) 0.093(13) Uiso d D 1 1 . .
H H5C 0.655(5) 0.416(3) 0.982(4) 0.055(16) Uiso d PDU 0.53(4) 1 A 1
H H6C 0.372(6) 0.342(4) 0.977(5) 0.07(2) Uiso d PD 0.53(4) 1 A 1
H H5C' 0.512(3) 0.308(6) 0.966(5) 0.064(17) Uiso d PDU 0.47(4) 1 A 2
H H6C' 0.696(9) 0.551(4) 1.010(6) 0.10(3) Uiso d PD 0.47(4) 1 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 '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
N1 C1 N2 . 106.45(17)
N1 C1 S1 . 127.77(15)
N2 C1 S1 . 125.78(15)
O1 C2 N2 . 128.10(19)
O1 C2 C3 . 128.15(19)
N2 C2 C3 . 103.75(17)
C4 C3 N1 . 128.45(18)
C4 C3 C2 . 125.31(18)
N1 C3 C2 . 106.24(16)
C3 C4 N4 . 127.29(18)
C3 C4 C5 . 127.39(18)
N4 C4 C5 . 105.32(16)
O2 C5 N3 . 127.62(19)
O2 C5 C4 . 127.65(19)
N3 C5 C4 . 104.73(17)
N4 C6 N3 . 106.40(17)
N4 C6 S3 . 128.59(16)
N3 C6 S3 . 125.01(15)
N5 C7 N6 . 106.53(18)
N5 C7 S2 . 127.50(16)
N6 C7 S2 . 125.97(16)
O3 C8 N6 . 127.64(19)
O3 C8 C9 . 128.35(19)
N6 C8 C9 . 104.01(17)
C9 C9 N5 2_776 127.9(2)
C9 C9 C8 2_776 126.1(2)
N5 C9 C8 . 105.95(17)
O4 C10 N7 . 126.3(2)
O4 C10 H10A . 116.9
N7 C10 H10A . 116.9
N7 C11 H11A . 109.5
N7 C11 H11B . 109.5
H11A C11 H11B . 109.5
N7 C11 H11C . 109.5
H11A C11 H11C . 109.5
H11B C11 H11C . 109.5
N7 C12 H12A . 109.5
N7 C12 H12B . 109.5
H12A C12 H12B . 109.5
N7 C12 H12C . 109.5
H12A C12 H12C . 109.5
H12B C12 H12C . 109.5
C1 N1 C3 . 111.05(16)
C1 N1 H1A . 124.5
C3 N1 H1A . 124.5
C1 N2 C2 . 112.49(17)
C1 N2 H2A . 124.6(17)
C2 N2 H2A . 122.6(17)
C5 N3 C6 . 112.15(17)
C5 N3 H3A . 124.4(17)
C6 N3 H3A . 122.7(18)
C6 N4 C4 . 111.39(17)
C6 N4 H4A . 123.6(15)
C4 N4 H4A . 125.0(16)
C7 N5 C9 . 111.07(18)
C7 N5 H5A . 123.5(17)
C9 N5 H5A . 125.5(17)
C8 N6 C7 . 112.34(18)
C8 N6 H6A . 120.7(17)
C7 N6 H6A . 125.8(17)
C10 N7 C11 . 121.3(2)
C10 N7 C12 . 121.2(2)
C11 N7 C12 . 117.4(2)
H5B O5 H5C . 104(4)
H5B O5 H6C' . 109(5)
H5C O5 H6C' . 110(5)
H6B O6 H6C . 106(5)
H6B O6 H5C' . 107(4)
H6C O6 H5C' . 108(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.364(2)
C1 N2 . 1.372(3)
C1 S1 . 1.646(2)
C2 O1 . 1.207(2)
C2 N2 . 1.376(3)
C2 C3 . 1.480(3)
C3 C4 . 1.347(3)
C3 N1 . 1.376(2)
C4 N4 . 1.389(3)
C4 C5 . 1.474(3)
C5 O2 . 1.221(2)
C5 N3 . 1.365(3)
C6 N4 . 1.353(3)
C6 N3 . 1.380(3)
C6 S3 . 1.644(2)
C7 N5 . 1.361(3)
C7 N6 . 1.374(3)
C7 S2 . 1.643(2)
C8 O3 . 1.212(2)
C8 N6 . 1.374(3)
C8 C9 . 1.479(3)
C9 C9 2_776 1.346(4)
C9 N5 . 1.382(3)
C10 O4 . 1.238(3)
C10 N7 . 1.314(3)
C10 H10A . 0.9300
C11 N7 . 1.454(3)
C11 H11A . 0.9600
C11 H11B . 0.9600
C11 H11C . 0.9600
C12 N7 . 1.455(3)
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
N1 H1A . 0.8600
N2 H2A . 0.78(2)
N3 H3A . 0.87(3)
N4 H4A . 0.76(2)
N5 H5A . 0.81(2)
N6 H6A . 0.81(2)
O5 H5B . 0.787(17)
O5 H5C . 0.788(17)
O5 H6C' . 0.788(17)
O6 H6B . 0.796(19)
O6 H6C . 0.796(19)
O6 H5C' . 0.796(19)
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
C11 H11A O3 2_766 0.96 2.56 3.495(3) 165.9
N1 H1A O2 . 0.86 2.57 3.059(2) 117.2
N1 H1A S3 1_455 0.86 2.55 3.3948(18) 166.8
N2 H2A O4 2_656 0.78(2) 1.99(2) 2.774(2) 175(2)
N3 H3A O5 2_767 0.87(3) 1.96(3) 2.803(2) 164(2)
N4 H4A O1 . 0.76(2) 2.52(2) 2.980(2) 119.9(18)
N4 H4A S1 1_655 0.76(2) 2.70(2) 3.448(2) 166.3(19)
N5 H5A O3 2_776 0.81(2) 2.56(2) 3.024(2) 118(2)
N5 H5A S2 2_676 0.81(2) 2.67(3) 3.466(2) 168(2)
N6 H6A O6 2_666 0.81(2) 2.04(2) 2.842(3) 174(2)
O5 H5B O2 . 0.787(17) 2.019(18) 2.805(2) 176(3)
O6 H6B O4 2_657 0.796(19) 2.026(19) 2.817(3) 173(3)
O5 H5C O6 . 0.788(17) 2.08(2) 2.843(3) 162(5)
O6 H6C O5 2_667 0.796(19) 2.12(2) 2.913(3) 172(6)
O6 H5C' O5 . 0.796(19) 2.14(3) 2.843(3) 148(5)
O5 H6C' O6 2_667 0.788(17) 2.127(19) 2.913(3) 175(7)
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_4
_geom_torsion
O1 C2 C3 C4 . . 1.1(4)
N2 C2 C3 C4 . . -179.1(2)
O1 C2 C3 N1 . . -179.1(2)
N2 C2 C3 N1 . . 0.6(2)
N1 C3 C4 N4 . . -179.9(2)
C2 C3 C4 N4 . . -0.2(4)
N1 C3 C4 C5 . . 0.7(4)
C2 C3 C4 C5 . . -179.7(2)
C3 C4 C5 O2 . . -0.8(4)
N4 C4 C5 O2 . . 179.6(2)
C3 C4 C5 N3 . . 180.0(2)
N4 C4 C5 N3 . . 0.4(2)
O3 C8 C9 C9 . 2_776 1.5(4)
N6 C8 C9 C9 . 2_776 -179.2(3)
O3 C8 C9 N5 . . -177.4(2)
N6 C8 C9 N5 . . 1.8(2)
N2 C1 N1 C3 . . -0.8(2)
S1 C1 N1 C3 . . 179.13(16)
C4 C3 N1 C1 . . 179.8(2)
C2 C3 N1 C1 . . 0.1(2)
N1 C1 N2 C2 . . 1.2(2)
S1 C1 N2 C2 . . -178.67(16)
O1 C2 N2 C1 . . 178.6(2)
C3 C2 N2 C1 . . -1.1(2)
O2 C5 N3 C6 . . -179.5(2)
C4 C5 N3 C6 . . -0.3(2)
N4 C6 N3 C5 . . 0.1(2)
S3 C6 N3 C5 . . 179.78(16)
N3 C6 N4 C4 . . 0.2(2)
S3 C6 N4 C4 . . -179.47(16)
C3 C4 N4 C6 . . -180.0(2)
C5 C4 N4 C6 . . -0.4(2)
N6 C7 N5 C9 . . -2.1(2)
S2 C7 N5 C9 . . 177.30(16)
C9 C9 N5 C7 2_776 . -178.8(3)
C8 C9 N5 C7 . . 0.1(2)
O3 C8 N6 C7 . . 176.1(2)
C9 C8 N6 C7 . . -3.2(2)
N5 C7 N6 C8 . . 3.4(2)
S2 C7 N6 C8 . . -175.98(16)
O4 C10 N7 C11 . . -177.5(2)
O4 C10 N7 C12 . . -2.1(4)
