#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/40/2224043.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_2224043
loop_
_publ_author_name
'Ueda, Kazumasa'
'Yoza, Kenji'
_publ_section_title
(5E)-2-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-5-(4-iodo-1,3-dithiol-2-ylidene)-1,3-dithiolan-4-one
_journal_coeditor_code           TK2559
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2920
_journal_paper_doi               10.1107/S1600536809044493
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H7 I O S8'
_chemical_formula_moiety         'C11 H7 I O S8'
_chemical_formula_sum            'C11 H7 I O S8'
_chemical_formula_weight         538.55
_chemical_name_systematic
;
(5E)-2-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-5-(4-iodo-1,3-
dithiol-2-ylidene)-1,3-dithiolan-4-one
;
_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                90.851(6)
_cell_angle_beta                 105.132(6)
_cell_angle_gamma                118.510(4)
_cell_formula_units_Z            2
_cell_length_a                   8.309(3)
_cell_length_b                   8.344(3)
_cell_length_c                   14.618(7)
_cell_measurement_reflns_used    2153
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.8
_cell_volume                     848.0(6)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'Mercury (Macrae et al.,  2008)'
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.050
_diffrn_reflns_av_sigmaI/netI    0.068
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9773
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.5
_exptl_absorpt_coefficient_mu    2.865
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            dark-red
_exptl_crystal_density_diffrn    2.109
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.34
_refine_diff_density_min         -1.13
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.070
_refine_ls_R_factor_gt           0.055
_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)+(0.0842P)²+3.4063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.153
_refine_ls_wR_factor_ref         0.161
_reflns_number_gt                3065
_reflns_number_total             3820
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2559.cif
_cod_data_source_block           I
_cod_database_code               2224043
_cod_database_fobs_code          2224043
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
C C1 0.7414(11) 0.3494(11) 1.2804(5) 0.0208(15) Uani d . 1 . .
C C2 0.7832(11) 0.2717(10) 1.2163(5) 0.0200(15) Uani d . 1 . .
H H2A 0.7957 0.1652 1.2252 0.024 Uiso calc R 1 . .
C C3 0.7600(10) 0.5445(10) 1.1458(5) 0.0171(14) Uani d . 1 . .
C C4 0.7523(10) 0.6656(10) 1.0854(5) 0.0147(14) Uani d . 1 . .
C C5 0.7096(11) 0.8045(10) 1.1130(5) 0.0176(15) Uani d . 1 . .
C C6 0.7518(10) 0.8433(10) 0.9411(5) 0.0188(15) Uani d . 1 . .
C C7 0.7691(10) 0.9104(10) 0.8586(5) 0.0168(14) Uani d . 1 . .
C C8 0.7811(11) 1.1023(10) 0.7195(5) 0.0195(15) Uani d . 1 . .
C C9 0.8259(11) 0.9774(10) 0.6922(6) 0.0227(16) Uani d . 1 . .
C C10 0.5811(14) 1.2907(13) 0.6735(8) 0.040(2) Uani d . 1 . .
H H10A 0.5663 1.3860 0.6401 0.060 Uiso calc R 1 . .
H H10B 0.6051 1.3221 0.7424 0.060 Uiso calc R 1 . .
H H10C 0.4633 1.1708 0.6481 0.060 Uiso calc R 1 . .
C C11 0.7773(12) 0.7290(12) 0.5471(7) 0.0317(19) Uani d . 1 . .
H H11A 0.8072 0.7093 0.4888 0.048 Uiso calc R 1 . .
H H11B 0.6381 0.6763 0.5324 0.048 Uiso calc R 1 . .
H H11C 0.8218 0.6686 0.5964 0.048 Uiso calc R 1 . .
I I1 0.72165(7) 0.26967(7) 1.41327(4) 0.02158(17) Uani d . 1 . .
O O1 0.6819(8) 0.8263(7) 1.1898(4) 0.0248(12) Uani d . 1 . .
S S2 0.6928(3) 0.9427(3) 1.02369(13) 0.0204(4) Uani d . 1 . .
S S3 0.7856(3) 0.6574(3) 0.97138(13) 0.0192(4) Uani d . 1 . .
S S4 0.7150(3) 0.5414(2) 1.25643(13) 0.0180(4) Uani d . 1 . .
S S5 0.8134(3) 0.3773(3) 1.11542(14) 0.0223(4) Uani d . 1 . .
S S6 0.7799(3) 1.2779(3) 0.65508(14) 0.0222(4) Uani d . 1 . .
S S7 0.8283(3) 0.8205(3) 0.77148(14) 0.0215(4) Uani d . 1 . .
S S8 0.7337(3) 1.0982(3) 0.83040(14) 0.0212(4) Uani d . 1 . .
S S9 0.8974(4) 0.9749(3) 0.59090(16) 0.0318(5) 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'
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'
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 S4 . . 118.7(6) ?
C2 C1 I1 . . 124.9(6) ?
S4 C1 I1 . . 116.2(4) ?
C1 C2 S5 . . 116.1(6) ?
C1 C2 H2A . . 122.0 ?
S5 C2 H2A . . 122.0 ?
C4 C3 S5 . . 121.0(6) ?
C4 C3 S4 . . 124.0(6) ?
S5 C3 S4 . . 115.1(4) ?
C3 C4 C5 . . 119.7(7) ?
C3 C4 S3 . . 122.9(6) ?
C5 C4 S3 . . 117.3(5) ?
O1 C5 C4 . . 124.7(7) ?
O1 C5 S2 . . 121.3(6) ?
C4 C5 S2 . . 113.9(5) ?
C7 C6 S2 . . 120.1(6) ?
C7 C6 S3 . . 123.1(6) ?
S2 C6 S3 . . 116.8(4) ?
C6 C7 S7 . . 123.5(6) ?
C6 C7 S8 . . 121.9(6) ?
S7 C7 S8 . . 114.6(4) ?
C9 C8 S6 . . 124.3(6) ?
C9 C8 S8 . . 118.1(6) ?
S6 C8 S8 . . 117.4(4) ?
C8 C9 S9 . . 124.2(6) ?
C8 C9 S7 . . 116.2(6) ?
S9 C9 S7 . . 119.4(5) ?
S6 C10 H10A . . 109.5 ?
S6 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
S6 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 ?
C6 S2 C5 . . 96.5(4) ?
C6 S3 C4 . . 95.3(3) ?
C1 S4 C3 . . 94.2(4) ?
C3 S5 C2 . . 95.8(4) ?
C8 S6 C10 . . 102.2(4) ?
C7 S7 C9 . . 96.0(4) ?
C7 S8 C8 . . 95.1(4) ?
C9 S9 C11 . . 101.7(4) ?
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 . 1.337(11) ?
C1 S4 . 1.746(8) ?
C1 I1 . 2.083(8) ?
C2 S5 . 1.741(8) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.365(10) ?
C3 S5 . 1.737(7) ?
C3 S4 . 1.751(8) ?
C4 C5 . 1.444(10) ?
C4 S3 . 1.764(7) ?
C5 O1 . 1.230(9) ?
C5 S2 . 1.777(8) ?
C6 C7 . 1.350(10) ?
C6 S2 . 1.747(8) ?
C6 S3 . 1.747(8) ?
C7 S7 . 1.755(7) ?
C7 S8 . 1.762(8) ?
C8 C9 . 1.349(11) ?
C8 S6 . 1.755(8) ?
C8 S8 . 1.763(7) ?
C9 S9 . 1.736(8) ?
C9 S7 . 1.765(8) ?
C10 S6 . 1.792(9) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 S9 . 1.813(9) ?
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 30655933
