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#$Date: 2023-03-09 11:23:10 +0200 (Thu, 09 Mar 2023) $
#$Revision: 281764 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106891.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106891
loop_
_publ_author_name
'Du, Xi-Gang'
'Wang, Chun-Wei'
_publ_section_title
;
 Crystal structure of
 2,2′-[(1E)-prop-1-ene-1,2-diyldisulfanediyl]bis(5-methyl-2,5-dihydro-1,3,4-thiadiazole,
 C9H10N4S4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              411
_journal_page_last               412
_journal_paper_doi               10.1515/ncrs-2015-0049
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C9 H10 N4 S4'
_chemical_formula_weight         302.45
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.215(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.668(2)
_cell_length_b                   23.957(9)
_cell_length_c                   10.160(4)
_cell_measurement_reflns_used    2401
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.23
_cell_measurement_theta_min      2.65
_cell_volume                     1357.7(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10229
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  0.9349
_exptl_absorpt_correction_T_min  0.8479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0381P)²+0.4842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0901
_reflns_number_gt                1874
_reflns_number_total             2513
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0049_suppl.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               8106891
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.3641(6) 0.43902(12) 0.4800(3) 0.0694(9) Uani 1 1 d . . .
H1A H 1.3067 0.4649 0.5391 0.104 Uiso 1 1 calc R . .
H1B H 1.3775 0.4576 0.3978 0.104 Uiso 1 1 calc R . .
H1C H 1.5186 0.4252 0.5213 0.104 Uiso 1 1 calc R . .
C2 C 1.1926(5) 0.39144(11) 0.4514(3) 0.0528(7) Uani 1 1 d . . .
C3 C 0.9787(5) 0.30891(10) 0.3817(3) 0.0481(6) Uani 1 1 d . . .
C4 C 0.6955(5) 0.22244(10) 0.4228(2) 0.0487(6) Uani 1 1 d . . .
H4 H 0.6954 0.2425 0.5011 0.058 Uiso 1 1 calc R . .
C5 C 0.5597(5) 0.17795(11) 0.3992(3) 0.0516(7) Uani 1 1 d . . .
C6 C 0.5336(7) 0.14316(14) 0.2746(3) 0.0864(11) Uani 1 1 d . . .
H6A H 0.3750 0.1477 0.2238 0.130 Uiso 1 1 calc R . .
H6B H 0.5596 0.1046 0.2985 0.130 Uiso 1 1 calc R . .
H6C H 0.6494 0.1549 0.2219 0.130 Uiso 1 1 calc R . .
C7 C 0.5123(4) 0.09826(11) 0.5817(2) 0.0455(6) Uani 1 1 d . . .
C8 C 0.7557(4) 0.02112(10) 0.6651(2) 0.0455(6) Uani 1 1 d . . .
C9 C 0.9432(5) -0.02232(12) 0.7045(3) 0.0598(7) Uani 1 1 d . . .
H9A H 0.9426 -0.0337 0.7951 0.090 Uiso 1 1 calc R . .
H9B H 1.0975 -0.0073 0.6978 0.090 Uiso 1 1 calc R . .
H9C H 0.9101 -0.0540 0.6462 0.090 Uiso 1 1 calc R . .
N1 N 0.9873(5) 0.38962(10) 0.4890(3) 0.0712(7) Uani 1 1 d . . .
N2 N 0.8603(4) 0.34139(10) 0.4478(3) 0.0716(7) Uani 1 1 d . . .
N3 N 0.3902(4) 0.05952(9) 0.6269(2) 0.0559(6) Uani 1 1 d . . .
N4 N 0.5346(4) 0.01477(9) 0.6765(2) 0.0529(6) Uani 1 1 d . . .
S1 S 1.25402(13) 0.33339(3) 0.36406(8) 0.0580(2) Uani 1 1 d . . .
S2 S 0.87757(14) 0.24505(3) 0.31016(7) 0.0602(2) Uani 1 1 d . . .
S3 S 0.37635(13) 0.16070(3) 0.51785(8) 0.0623(2) Uani 1 1 d . . .
S4 S 0.81263(12) 0.08427(3) 0.59455(8) 0.0544(2) Uani 1 1 d . . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 C1 124.1(3) . .
N1 C2 S1 113.7(2) . .
C1 C2 S1 122.2(2) . .
N2 C3 S1 114.63(19) . .
N2 C3 S2 125.6(2) . .
S1 C3 S2 119.73(16) . .
C5 C4 S2 121.7(2) . .
C5 C4 H4 119.2 . .
S2 C4 H4 119.2 . .
C4 C5 C6 124.9(3) . .
C4 C5 S3 117.4(2) . .
C6 C5 S3 117.5(2) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N3 C7 S4 114.8(2) . .
N3 C7 S3 121.15(19) . .
S4 C7 S3 124.00(14) . .
N4 C8 C9 123.5(2) . .
N4 C8 S4 113.4(2) . .
C9 C8 S4 123.10(18) . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C2 N1 N2 112.8(2) . .
C3 N2 N1 111.7(2) . .
C7 N3 N4 111.5(2) . .
C8 N4 N3 113.4(2) . .
C3 S1 C2 87.18(13) . .
C3 S2 C4 100.73(12) . .
C7 S3 C5 100.27(12) . .
C7 S4 C8 86.96(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.493(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 N1 1.288(3) .
C2 S1 1.719(3) .
C3 N2 1.290(3) .
C3 S1 1.706(3) .
C3 S2 1.746(3) .
C4 C5 1.312(3) .
C4 S2 1.757(3) .
C4 H4 0.9300 .
C5 C6 1.500(4) .
C5 S3 1.774(3) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 N3 1.290(3) .
C7 S4 1.717(3) .
C7 S3 1.754(3) .
C8 N4 1.288(3) .
C8 C9 1.490(4) .
C8 S4 1.729(3) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
N1 N2 1.386(3) .
N3 N4 1.388(3) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
S2 C4 C5 C6 -2.9(4) . . . .
S2 C4 C5 S3 -177.95(14) . . . .
C1 C2 N1 N2 178.9(3) . . . .
S1 C2 N1 N2 -1.2(3) . . . .
S1 C3 N2 N1 0.3(3) . . . .
S2 C3 N2 N1 -178.6(2) . . . .
C2 N1 N2 C3 0.5(4) . . . .
S4 C7 N3 N4 0.1(3) . . . .
S3 C7 N3 N4 -177.97(18) . . . .
C9 C8 N4 N3 -176.8(2) . . . .
S4 C8 N4 N3 1.3(3) . . . .
C7 N3 N4 C8 -0.9(3) . . . .
N2 C3 S1 C2 -0.8(2) . . . .
S2 C3 S1 C2 178.17(17) . . . .
N1 C2 S1 C3 1.1(2) . . . .
C1 C2 S1 C3 -178.9(2) . . . .
N2 C3 S2 C4 -31.5(3) . . . .
S1 C3 S2 C4 149.63(16) . . . .
C5 C4 S2 C3 172.3(2) . . . .
N3 C7 S3 C5 -150.5(2) . . . .
S4 C7 S3 C5 31.59(19) . . . .
C4 C5 S3 C7 -112.8(2) . . . .
C6 C5 S3 C7 71.8(3) . . . .
N3 C7 S4 C8 0.5(2) . . . .
S3 C7 S4 C8 178.51(18) . . . .
N4 C8 S4 C7 -1.0(2) . . . .
C9 C8 S4 C7 177.1(2) . . . .
