#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/26/2202620.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_2202620
loop_
_publ_author_name
'Chohan, Zahid H.'
'Comerlato, Nadia M.'
'Howie, R. Alan'
'Skakle, Janet M. S.'
'Wardell, James L.'
_publ_section_title
;
 1,4-Dimethylpyridinium
 bis(2-oxo-1,3-dithiole-4,5-dithiolato)diphenylantimonate(V)
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1006
_journal_page_last               m1009
_journal_paper_doi               10.1107/S1600536803022190
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '(C7 H10 N) [Sb (C6 H5)2 (C3 O S4)2]'
_chemical_formula_moiety         'C7 H10 N + , C18 H10 O2 S8 Sb -'
_chemical_formula_sum            'C25 H20 N O2 S8 Sb'
_chemical_formula_weight         744.65
_chemical_name_systematic
;
1,4-Dimethylpyridinium
bis(2-oxo-1,3-dithiole-4,5-dithiolato)diphenylantimonate(1-)
;
_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     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                94.0630(10)
_cell_angle_beta                 112.1260(10)
_cell_angle_gamma                108.1370(10)
_cell_formula_units_Z            2
_cell_length_a                   10.7513(5)
_cell_length_b                   12.0130(6)
_cell_length_c                   13.5273(6)
_cell_measurement_reflns_used    4647
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      30.82
_cell_measurement_theta_min      2.19
_cell_volume                     1502.53(12)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.021
_diffrn_reflns_av_sigmaI/netI    0.057
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15605
_diffrn_reflns_theta_full        32.49
_diffrn_reflns_theta_max         32.49
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.499
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            dark_red
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.69
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         10417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.882
_refine_ls_R_factor_all          0.073
_refine_ls_R_factor_gt           0.038
_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)+(0.0267P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.064
_refine_ls_wR_factor_ref         0.072
_reflns_number_gt                6570
_reflns_number_total             10417
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn6098.cif
_cod_data_source_block           IV
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2202620
_cod_database_fobs_code          2202620
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
Sb1 0.421630(17) 0.733698(14) 0.681622(13) 0.03959(5) Uani d . 1 . . Sb
S1 0.45887(7) 0.86198(7) 0.54656(6) 0.05796(19) Uani d . 1 . . S
S2 0.24662(7) 0.57986(6) 0.49951(5) 0.05231(16) Uani d . 1 . . S
C1 0.2770(3) 0.8025(2) 0.4556(2) 0.0476(6) Uani d . 1 . . C
C2 0.1896(3) 0.6869(2) 0.43718(19) 0.0448(6) Uani d . 1 . . C
S3 0.19484(8) 0.89987(7) 0.39370(7) 0.0672(2) Uani d . 1 . . S
S4 0.00604(7) 0.65030(6) 0.35519(6) 0.05879(18) Uani d . 1 . . S
C3 0.0174(3) 0.7930(3) 0.3278(2) 0.0607(7) Uani d . 1 . . C
O1 -0.0849(2) 0.8162(2) 0.2703(2) 0.0872(7) Uani d . 1 . . O
S5 0.39255(7) 0.57547(6) 0.79636(5) 0.05075(16) Uani d . 1 . . S
S6 0.59876(8) 0.63498(8) 0.66380(5) 0.05920(19) Uani d . 1 . . S
C4 0.5764(3) 0.5996(2) 0.8544(2) 0.0454(6) Uani d . 1 . . C
C5 0.6611(3) 0.6242(2) 0.7994(2) 0.0476(6) Uani d . 1 . . C
S7 0.66348(8) 0.60820(8) 0.99454(6) 0.0646(2) Uani d . 1 . . S
S8 0.84595(8) 0.66227(8) 0.87580(6) 0.0639(2) Uani d . 1 . . S
C6 0.8405(3) 0.6467(3) 1.0031(2) 0.0686(8) Uani d . 1 . . C
O2 0.9450(2) 0.6579(3) 1.08531(18) 0.0983(8) Uani d . 1 . . O
C7 0.5954(3) 0.8689(2) 0.8200(2) 0.0489(6) Uani d . 1 . . C
C8 0.5750(3) 0.8930(3) 0.9124(3) 0.0717(9) Uani d . 1 . . C
H8 0.4867 0.8535 0.9141 0.086 Uiso calc R 1 . . H
C9 0.6872(4) 0.9767(4) 1.0032(3) 0.0983(12) Uani d . 1 . . C
H9 0.6744 0.9918 1.0664 0.118 Uiso calc R 1 . . H
C10 0.8156(5) 1.0368(4) 1.0004(4) 0.1048(14) Uani d . 1 . . C
H10 0.8906 1.0919 1.0620 0.126 Uiso calc R 1 . . H
C11 0.8344(4) 1.0165(3) 0.9078(4) 0.0948(12) Uani d . 1 . . C
H11 0.9210 1.0600 0.9053 0.114 Uiso calc R 1 . . H
C12 0.7251(3) 0.9314(3) 0.8169(3) 0.0674(8) Uani d . 1 . . C
H12 0.7392 0.9164 0.7543 0.081 Uiso calc R 1 . . H
C13 0.2449(3) 0.7812(2) 0.68571(19) 0.0440(5) Uani d . 1 . . C
C14 0.1186(3) 0.6945(3) 0.6742(2) 0.0599(7) Uani d . 1 . . C
H14 0.1095 0.6145 0.6664 0.072 Uiso calc R 1 . . H
C15 0.0051(3) 0.7254(3) 0.6740(3) 0.0766(10) Uani d . 1 . . C
H15 -0.0796 0.6662 0.6670 0.092 Uiso calc R 1 . . H
C16 0.0169(4) 0.8421(4) 0.6842(3) 0.0864(11) Uani d . 1 . . C
H16 -0.0596 0.8627 0.6842 0.104 Uiso calc R 1 . . H
C17 0.1409(4) 0.9288(3) 0.6946(3) 0.0919(11) Uani d . 1 . . C
H17 0.1481 1.0084 0.7004 0.110 Uiso calc R 1 . . H
C18 0.2562(3) 0.8991(3) 0.6965(3) 0.0682(8) Uani d . 1 . . C
H18 0.3413 0.9589 0.7052 0.082 Uiso calc R 1 . . H
N1 0.4496(3) 0.2959(2) 0.6888(2) 0.0679(7) Uani d . 1 . . N
C19 0.5859(4) 0.3255(3) 0.7008(3) 0.0828(10) Uani d . 1 . . C
H19 0.6074 0.3413 0.6415 0.099 Uiso calc R 1 . . H
C20 0.6939(4) 0.3328(3) 0.7980(3) 0.0821(10) Uani d . 1 . . C
H20 0.7875 0.3522 0.8038 0.099 Uiso calc R 1 . . H
C21 0.6661(4) 0.3118(3) 0.8881(3) 0.0710(9) Uani d . 1 . . C
C22 0.5253(4) 0.2827(3) 0.8729(3) 0.0803(10) Uani d . 1 . . C
H22 0.5021 0.2682 0.9316 0.096 Uiso calc R 1 . . H
C23 0.4188(3) 0.2743(3) 0.7750(3) 0.0721(9) Uani d . 1 . . C
H23 0.3243 0.2536 0.7673 0.087 Uiso calc R 1 . . H
C24 0.3343(4) 0.2913(4) 0.5839(3) 0.1027(13) Uani d . 1 . . C
H24A 0.2440 0.2685 0.5899 0.154 Uiso calc PR 0.50 . . H
H24B 0.3278 0.2335 0.5275 0.154 Uiso calc PR 0.50 . . H
H24C 0.3560 0.3688 0.5658 0.154 Uiso calc PR 0.50 . . H
H24D 0.3746 0.3121 0.5323 0.154 Uiso calc PR 0.50 . . H
H24E 0.2908 0.3470 0.5946 0.154 Uiso calc PR 0.50 . . H
H24F 0.2625 0.2117 0.5564 0.154 Uiso calc PR 0.50 . . H
C25 0.7837(4) 0.3268(4) 0.9976(3) 0.1086(14) Uani d . 1 . . C
H25A 0.8741 0.3471 0.9918 0.163 Uiso calc PR 0.50 . . H
H25B 0.7638 0.2533 1.0227 0.163 Uiso calc PR 0.50 . . H
H25C 0.7888 0.3898 1.0485 0.163 Uiso calc PR 0.50 . . H
H25D 0.7437 0.3130 1.0502 0.163 Uiso calc PR 0.50 . . H
H25E 0.8540 0.4068 1.0193 0.163 Uiso calc PR 0.50 . . H
H25F 0.8290 0.2703 0.9935 0.163 Uiso calc PR 0.50 . . H
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'
Sb Sb -0.5866 1.5461 '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
C7 Sb1 C13 98.25(9)
C7 Sb1 S1 92.69(7)
C13 Sb1 S1 94.08(7)
C7 Sb1 S5 93.13(7)
C13 Sb1 S5 94.26(7)
S1 Sb1 S5 169.05(3)
C7 Sb1 S2 169.47(7)
C13 Sb1 S2 89.91(7)
S1 Sb1 S2 80.03(2)
S5 Sb1 S2 92.89(2)
C7 Sb1 S6 90.82(7)
C13 Sb1 S6 169.12(7)
S1 Sb1 S6 91.48(2)
S5 Sb1 S6 79.17(2)
S2 Sb1 S6 81.83(2)
C1 S1 Sb1 93.54(8)
C2 S2 Sb1 92.58(9)
C2 C1 S1 124.24(19)
C2 C1 S3 116.66(19)
S1 C1 S3 118.76(15)
C1 C2 S2 123.81(19)
C1 C2 S4 116.72(19)
S2 C2 S4 119.20(14)
C1 S3 C3 96.89(13)
C2 S4 C3 97.18(12)
O1 C3 S4 124.1(2)
O1 C3 S3 123.4(2)
S4 C3 S3 112.54(16)
C4 S5 Sb1 93.32(8)
C5 S6 Sb1 92.66(9)
C5 C4 S5 123.83(19)
C5 C4 S7 116.64(19)
S5 C4 S7 119.20(14)
C4 C5 S6 123.74(19)
C4 C5 S8 116.78(19)
S6 C5 S8 119.12(14)
C4 S7 C6 97.27(13)
C5 S8 C6 97.33(13)
O2 C6 S8 123.7(2)
O2 C6 S7 124.3(2)
S8 C6 S7 111.93(16)
C8 C7 C12 119.7(3)
C8 C7 Sb1 118.9(2)
C12 C7 Sb1 121.4(2)
C7 C8 C9 119.6(3)
C7 C8 H8 120.2
C9 C8 H8 120.2
C10 C9 C8 120.5(4)
C10 C9 H9 119.8
C8 C9 H9 119.8
C11 C10 C9 120.1(4)
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C12 120.4(4)
C10 C11 H11 119.8
C12 C11 H11 119.8
C7 C12 C11 119.6(3)
C7 C12 H12 120.2
C11 C12 H12 120.2
C14 C13 C18 119.0(3)
C14 C13 Sb1 121.0(2)
C18 C13 Sb1 120.05(19)
C13 C14 C15 120.5(3)
C13 C14 H14 119.7
C15 C14 H14 119.7
C16 C15 C14 120.1(3)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C17 120.0(3)
C15 C16 H16 120.0
C17 C16 H16 120.0
C16 C17 C18 120.4(3)
C16 C17 H17 119.8
C18 C17 H17 119.8
C13 C18 C17 120.0(3)
C13 C18 H18 120.0
C17 C18 H18 120.0
C19 N1 C23 119.4(3)
C19 N1 C24 120.8(3)
C23 N1 C24 119.8(3)
N1 C19 C20 121.3(3)
N1 C19 H19 119.4
C20 C19 H19 119.4
C19 C20 C21 120.8(3)
C19 C20 H20 119.6
C21 C20 H20 119.6
C22 C21 C20 116.2(3)
C22 C21 C25 121.8(3)
C20 C21 C25 122.0(3)
C23 C22 C21 122.2(3)
C23 C22 H22 118.9
C21 C22 H22 118.9
N1 C23 C22 120.1(3)
N1 C23 H23 119.9
C22 C23 H23 119.9
N1 C24 H24A 109.5
N1 C24 H24B 109.5
H24A C24 H24B 109.5
N1 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
N1 C24 H24D 109.5
H24A C24 H24D 141.1
H24B C24 H24D 56.3
H24C C24 H24D 56.3
N1 C24 H24E 109.5
H24A C24 H24E 56.3
H24B C24 H24E 141.1
H24C C24 H24E 56.3
H24D C24 H24E 109.5
N1 C24 H24F 109.5
H24A C24 H24F 56.3
H24B C24 H24F 56.3
H24C C24 H24F 141.1
H24D C24 H24F 109.5
H24E C24 H24F 109.5
C21 C25 H25A 109.5
C21 C25 H25B 109.5
H25A C25 H25B 109.5
C21 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
C21 C25 H25D 109.5
H25A C25 H25D 141.1
H25B C25 H25D 56.3
H25C C25 H25D 56.3
C21 C25 H25E 109.5
H25A C25 H25E 56.3
H25B C25 H25E 141.1
H25C C25 H25E 56.3
H25D C25 H25E 109.5
C21 C25 H25F 109.5
H25A C25 H25F 56.3
H25B C25 H25F 56.3
H25C C25 H25F 141.1
H25D C25 H25F 109.5
H25E C25 H25F 109.5
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
Sb1 C7 . 2.163(3) ?
Sb1 C13 . 2.165(2) ?
Sb1 S1 . 2.5376(6) ?
Sb1 S5 . 2.5561(6) ?
Sb1 S2 . 2.5929(7) ?
Sb1 S6 . 2.6081(7) ?
S1 C1 . 1.744(2) ?
S2 C2 . 1.731(2) ?
C1 C2 . 1.355(3) ?
C1 S3 . 1.753(3) ?
C2 S4 . 1.749(2) ?
S3 C3 . 1.764(3) ?
S4 C3 . 1.756(3) ?
C3 O1 . 1.212(3) ?
S5 C4 . 1.746(2) ?
S6 C5 . 1.729(2) ?
C4 C5 . 1.359(3) ?
C4 S7 . 1.748(2) ?
C5 S8 . 1.746(2) ?
S7 C6 . 1.768(3) ?
S8 C6 . 1.766(3) ?
C6 O2 . 1.209(3) ?
C7 C8 . 1.374(4) ?
C7 C12 . 1.381(4) ?
C8 C9 . 1.389(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.360(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.360(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.387(5) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.375(3) ?
C13 C18 . 1.376(4) ?
C14 C15 . 1.381(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.360(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.362(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.385(4) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
N1 C19 . 1.337(4) ?
N1 C23 . 1.348(4) ?
N1 C24 . 1.475(4) ?
C19 C20 . 1.362(4) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.382(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.371(4) ?
C21 C25 . 1.494(4) ?
C22 C23 . 1.358(4) ?
C22 H22 . 0.9300 ?
C23 H23 . 0.9300 ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C24 H24C . 0.9600 ?
C24 H24D . 0.9600 ?
C24 H24E . 0.9600 ?
C24 H24F . 0.9600 ?
C25 H25A . 0.9600 ?
C25 H25B . 0.9600 ?
C25 H25C . 0.9600 ?
C25 H25D . 0.9600 ?
C25 H25E . 0.9600 ?
C25 H25F . 0.9600 ?
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
C17 H17 O1 2_576 0.93 2.46 3.336(4) 158
C23 H23 O1 2_566 0.93 2.28 3.204(4) 173
C24 H24D S6 2_666 0.96 2.87 3.790(4) 162
C25 H25A O2 2_767 0.96 2.54 3.457(4) 159
