#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/22/8102269.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_8102269
loop_
_publ_author_name
'Agnes Bittermann'
'Klaus Wurst'
'Benno Bildstein'
_publ_section_title
;
 Crystal structure of crystal structure of
 4,5,9,10-tetrathiocino[1,2-b;5,6-b']diimidazolyl
 -1,3,6,8-tetramethyl-2,7-dione, C10H12N4O2S4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              233
_journal_volume                  223
_journal_year                    2008
_chemical_formula_sum            'C10 H12 N4 O2 S4'
_chemical_formula_weight         348.48
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.119(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0719(6)
_cell_length_b                   11.4131(4)
_cell_length_c                   8.3310(3)
_cell_measurement_reflns_used    7223
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.00
_cell_volume                     1430.95(9)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
 DENZO (Otwinowski & Minor, 1997) and SCALEPACK 
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997) [4]'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997) [3]'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997) [2]'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7470
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0046(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0329
_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)+(0.0408P)²+0.6359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                2056
_reflns_number_total             2497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2238.cff
_cod_data_source_block           bit2
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               8102269
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
S1 S 0.36202(4) 0.41863(6) 0.91460(7) 0.04000(19) Uani 1 1 d . . .
S2 S 0.46670(4) 0.45419(6) 0.76927(8) 0.0522(2) Uani 1 1 d . . .
S3 S 0.44939(4) 0.62547(7) 0.70696(9) 0.0575(2) Uani 1 1 d . . .
S4 S 0.34801(4) 0.62540(6) 0.52842(7) 0.0451(2) Uani 1 1 d . . .
O1 O 0.15727(10) 0.14305(13) 0.5998(2) 0.0446(4) Uani 1 1 d . . .
O2 O 0.08037(12) 0.80306(15) 0.7741(2) 0.0612(5) Uani 1 1 d . . .
N1 N 0.26333(11) 0.24946(15) 0.7526(2) 0.0320(4) Uani 1 1 d . . .
N2 N 0.15810(10) 0.34706(15) 0.6200(2) 0.0302(4) Uani 1 1 d . . .
N3 N 0.21140(12) 0.74619(15) 0.6592(2) 0.0395(5) Uani 1 1 d . . .
N4 N 0.12519(12) 0.60830(15) 0.7477(2) 0.0354(4) Uani 1 1 d . . .
C1 C 0.18894(13) 0.23541(19) 0.6519(3) 0.0327(5) Uani 1 1 d . . .
C2 C 0.27884(13) 0.36788(18) 0.7811(2) 0.0307(5) Uani 1 1 d . . .
C3 C 0.21399(12) 0.42877(17) 0.6982(2) 0.0275(5) Uani 1 1 d . . .
C4 C 0.19905(13) 0.55350(18) 0.6894(2) 0.0298(5) Uani 1 1 d . . .
C5 C 0.25249(14) 0.63913(18) 0.6322(2) 0.0334(5) Uani 1 1 d . . .
C6 C 0.13255(16) 0.7283(2) 0.7310(3) 0.0426(6) Uani 1 1 d . . .
C7 C 0.31064(16) 0.1504(2) 0.8266(3) 0.0422(6) Uani 1 1 d . . .
H7A H 0.3590 0.1278 0.7609 0.063 Uiso 1 1 calc R . .
H7B H 0.2701 0.0850 0.8353 0.063 Uiso 1 1 calc R . .
H7C H 0.3343 0.1724 0.9329 0.063 Uiso 1 1 calc R . .
C8 C 0.08498(14) 0.3708(2) 0.5029(3) 0.0421(6) Uani 1 1 d . . .
H8A H 0.0297 0.3739 0.5571 0.063 Uiso 1 1 calc R . .
H8B H 0.0817 0.3091 0.4228 0.063 Uiso 1 1 calc R . .
H8C H 0.0949 0.4454 0.4509 0.063 Uiso 1 1 calc R . .
C9 C 0.24477(19) 0.8608(2) 0.6174(3) 0.0514(7) Uani 1 1 d . . .
H9A H 0.2022 0.9204 0.6447 0.077 Uiso 1 1 calc R . .
H9B H 0.2535 0.8636 0.5029 0.077 Uiso 1 1 calc R . .
H9C H 0.3009 0.8750 0.6766 0.077 Uiso 1 1 calc R . .
C10 C 0.05750(14) 0.5535(2) 0.8419(3) 0.0423(6) Uani 1 1 d . . .
H10A H 0.0160 0.5108 0.7708 0.064 Uiso 1 1 calc R . .
H10B H 0.0259 0.6136 0.8982 0.064 Uiso 1 1 calc R . .
H10C H 0.0857 0.4999 0.9192 0.064 Uiso 1 1 calc R . .
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'
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'
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
_geom_angle_publ_flag
C2 S1 S2 103.72(7) . . ?
S3 S2 S1 104.18(4) . . ?
S2 S3 S4 105.18(4) . . ?
C5 S4 S3 104.05(8) . . ?
C1 N1 C2 110.01(17) . . ?
C1 N1 C7 122.22(18) . . ?
C2 N1 C7 127.50(18) . . ?
C1 N2 C3 109.86(17) . . ?
C1 N2 C8 122.45(18) . . ?
C3 N2 C8 127.16(18) . . ?
C6 N3 C5 110.03(18) . . ?
C6 N3 C9 123.9(2) . . ?
C5 N3 C9 126.1(2) . . ?
C6 N4 C4 109.96(18) . . ?
C6 N4 C10 122.71(19) . . ?
C4 N4 C10 126.30(18) . . ?
O1 C1 N1 127.3(2) . . ?
O1 C1 N2 127.3(2) . . ?
N1 C1 N2 105.41(17) . . ?
C3 C2 N1 107.54(18) . . ?
C3 C2 S1 129.22(16) . . ?
N1 C2 S1 123.01(15) . . ?
C2 C3 N2 107.18(18) . . ?
C2 C3 C4 129.59(19) . . ?
N2 C3 C4 123.21(18) . . ?
C5 C4 N4 107.37(18) . . ?
C5 C4 C3 128.99(19) . . ?
N4 C4 C3 123.59(18) . . ?
C4 C5 N3 107.14(18) . . ?
C4 C5 S4 129.22(17) . . ?
N3 C5 S4 123.40(16) . . ?
O2 C6 N3 127.4(2) . . ?
O2 C6 N4 127.1(2) . . ?
N3 C6 N4 105.48(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.730(2) . ?
S1 S2 2.0804(9) . ?
S2 S3 2.0357(11) . ?
S3 S4 2.0736(9) . ?
S4 C5 1.726(2) . ?
O1 C1 1.227(3) . ?
O2 C6 1.227(3) . ?
N1 C1 1.373(3) . ?
N1 C2 1.390(3) . ?
N1 C7 1.456(3) . ?
N2 C1 1.377(3) . ?
N2 C3 1.394(3) . ?
N2 C8 1.457(3) . ?
N3 C6 1.374(3) . ?
N3 C5 1.394(3) . ?
N3 C9 1.451(3) . ?
N4 C6 1.382(3) . ?
N4 C4 1.387(3) . ?
N4 C10 1.461(3) . ?
C2 C3 1.357(3) . ?
C3 C4 1.442(3) . ?
C4 C5 1.369(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653933
