#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/37/2223704.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_2223704
loop_
_publ_author_name
'Ueda, Kazumasa'
'Yoza, Kenji'
_publ_section_title
5-(4,5-Diiodo-1,3-dithiol-2-ylidene)-4',5'-bis(methylsulfanyl)-2,2'-bi-1,3-dithiole-4(5H)-thione
_journal_coeditor_code           CV2627
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2831
_journal_paper_doi               10.1107/S1600536809042573
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H6 I2 S9'
_chemical_formula_moiety         'C11 H6 I2 S9'
_chemical_formula_sum            'C11 H6 I2 S9'
_chemical_formula_weight         680.50
_chemical_name_systematic
;
5-(4,5-Diiodo-1,3-dithiol-2-ylidene)-4',5'-bis(methylsulfanyl)-2,2'-bi-1,3-
dithiole-4(5H)-thione
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.544(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.540(7)
_cell_length_b                   5.3543(13)
_cell_length_c                   25.163(6)
_cell_measurement_reflns_used    2871
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.43
_cell_volume                     3869.3(16)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'XCIF (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10568
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    4.213
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_correction_T_min  0.2053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2576
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.01
_refine_diff_density_max         3.445
_refine_diff_density_min         -2.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         4387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0280P)²+20.8292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0898
_reflns_number_gt                3536
_reflns_number_total             4387
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2627.cif
_cod_data_source_block           I
_cod_original_cell_volume        3869.2(16)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2223704
_cod_database_fobs_code          2223704
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 1.01287(15) 1.3727(9) 0.35298(19) 0.0158(10) Uani d . 1 . .
C C2 1.02057(16) 1.2692(10) 0.4024(2) 0.0198(11) Uani d . 1 . .
C C3 0.94845(15) 1.0393(9) 0.34447(18) 0.0150(10) Uani d . 1 . .
C C4 0.91248(16) 0.8707(9) 0.32900(19) 0.0157(10) Uani d . 1 . .
C C5 0.88305(16) 0.8507(9) 0.27608(19) 0.0152(10) Uani d . 1 . .
C C6 0.85596(16) 0.5009(9) 0.3338(2) 0.0177(10) Uani d . 1 . .
C C7 0.83308(16) 0.3149(10) 0.35177(19) 0.0180(11) Uani d . 1 . .
C C8 0.80459(17) -0.0037(10) 0.4151(2) 0.0213(11) Uani d . 1 . .
C C9 0.77585(16) -0.0346(10) 0.3660(2) 0.0197(11) Uani d . 1 . .
C C10 0.8099(2) 0.0697(12) 0.5245(2) 0.0345(14) Uani d . 1 . .
H H10A 0.8431 0.1096 0.5359 0.052 Uiso calc R 1 . .
H H10B 0.7988 0.0128 0.5562 0.052 Uiso calc R 1 . .
H H10C 0.7925 0.2190 0.5090 0.052 Uiso calc R 1 . .
C C11 0.68641(17) -0.0497(11) 0.3739(2) 0.0244(12) Uani d . 1 . .
H H11A 0.6975 -0.0211 0.4132 0.037 Uiso calc R 1 . .
H H11B 0.6563 -0.1358 0.3667 0.037 Uiso calc R 1 . .
H H11C 0.6828 0.1110 0.3547 0.037 Uiso calc R 1 . .
I I1 1.052758(10) 1.64937(6) 0.326836(12) 0.01695(10) Uani d . 1 . .
I I2 1.075939(14) 1.33621(9) 0.468614(15) 0.04003(14) Uani d . 1 . .
S S1 0.96539(4) 1.2618(2) 0.30265(5) 0.0163(2) Uani d . 1 . .
S S2 0.98132(4) 1.0369(3) 0.41150(5) 0.0202(3) Uani d . 1 . .
S S3 0.88601(4) 1.0394(2) 0.22343(5) 0.0186(3) Uani d . 1 . .
S S4 0.90284(4) 0.6524(2) 0.37793(5) 0.0196(3) Uani d . 1 . .
S S5 0.84272(4) 0.6130(2) 0.26660(5) 0.0194(3) Uani d . 1 . .
S S6 0.84983(4) 0.2173(3) 0.42068(5) 0.0217(3) Uani d . 1 . .
S S7 0.78627(4) 0.1484(3) 0.31171(5) 0.0200(3) Uani d . 1 . .
S S8 0.80104(5) -0.1743(3) 0.47356(5) 0.0231(3) Uani d . 1 . .
S S9 0.72837(4) -0.2411(3) 0.34965(5) 0.0200(3) Uani d . 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 0.0000 0.0000 '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'
I I -0.4742 1.8119 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 S1 . . 117.7(4) ?
C2 C1 I1 . . 127.1(4) ?
S1 C1 I1 . . 115.2(2) ?
C1 C2 S2 . . 116.4(4) ?
C1 C2 I2 . . 127.5(4) ?
S2 C2 I2 . . 116.1(3) ?
C4 C3 S2 . . 119.2(4) ?
C4 C3 S1 . . 126.1(4) ?
S2 C3 S1 . . 114.7(3) ?
C3 C4 C5 . . 125.4(5) ?
C3 C4 S4 . . 118.4(4) ?
C5 C4 S4 . . 116.2(4) ?
C4 C5 S3 . . 124.2(4) ?
C4 C5 S5 . . 116.1(4) ?
S3 C5 S5 . . 119.8(3) ?
C7 C6 S5 . . 124.4(4) ?
C7 C6 S4 . . 121.0(4) ?
S5 C6 S4 . . 114.6(3) ?
C6 C7 S7 . . 125.2(4) ?
C6 C7 S6 . . 120.2(4) ?
S7 C7 S6 . . 114.6(3) ?
C9 C8 S8 . . 124.1(4) ?
C9 C8 S6 . . 117.5(4) ?
S8 C8 S6 . . 118.4(3) ?
C8 C9 S9 . . 126.4(4) ?
C8 C9 S7 . . 117.3(4) ?
S9 C9 S7 . . 116.2(3) ?
S8 C10 H10A . . 109.5 ?
S8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
S8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
S9 C11 H11A . . 109.5 ?
S9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
S9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C3 S1 C1 . . 95.1(2) ?
C3 S2 C2 . . 96.0(2) ?
C6 S4 C4 . . 95.5(2) ?
C5 S5 C6 . . 97.4(2) ?
C8 S6 C7 . . 95.0(2) ?
C7 S7 C9 . . 95.4(2) ?
C8 S8 C10 . . 101.0(3) ?
C9 S9 C11 . . 97.8(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.331(7) ?
C1 S1 . 1.758(5) ?
C1 I1 . 2.093(5) ?
C2 S2 . 1.751(5) ?
C2 I2 . 2.074(5) ?
C3 C4 . 1.379(7) ?
C3 S2 . 1.738(4) ?
C3 S1 . 1.739(5) ?
C4 C5 . 1.414(6) ?
C4 S4 . 1.769(5) ?
C5 S3 . 1.685(5) ?
C5 S5 . 1.721(5) ?
C6 C7 . 1.340(7) ?
C6 S5 . 1.750(5) ?
C6 S4 . 1.758(5) ?
C7 S7 . 1.752(5) ?
C7 S6 . 1.767(5) ?
C8 C9 . 1.336(7) ?
C8 S8 . 1.755(5) ?
C8 S6 . 1.766(5) ?
C9 S9 . 1.758(5) ?
C9 S7 . 1.766(5) ?
C10 S8 . 1.806(6) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 S9 . 1.820(5) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743583
