#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/58/2205850.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_2205850
loop_
_publ_author_name
'Lei Wang'
'Jing-Ping Zhang'
'Bin Zhang'
_publ_section_title
;
 Bis[tetrakis(methylsulfanyl)tetrathiafulvalenium] oxalate dichloride
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1674
_journal_page_last               o1676
_journal_paper_doi               10.1107/S1600536805014121
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '2C10 H12 S8 2+ , C2 O4 2- , 2Cl -'
_chemical_formula_moiety         '2C10 H12 S8 2+ , C2 O4 2- , 2Cl -'
_chemical_formula_sum            'C22 H24 Cl2 O4 S16'
_chemical_formula_weight         936.28
_chemical_name_systematic
;
Bis[tetrakis(methylsulfanyl)tetrathiafulvalenium] oxalate dichloride
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.9850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0277(2)
_cell_length_b                   7.9202(2)
_cell_length_c                   23.2669(6)
_cell_measurement_reflns_used    27130
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.340
_cell_volume                     1847.62(8)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997--2000)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_molecular_graphics    'XP (Bruker, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius KappaCCD 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  0.0757
_diffrn_reflns_av_sigmaI/netI    0.0861
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24473
_diffrn_reflns_theta_full        27.65
_diffrn_reflns_theta_max         27.65
_diffrn_reflns_theta_min         3.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.111
_exptl_absorpt_correction_T_max  0.8970
_exptl_absorpt_correction_T_min  0.8250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.91
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.91
_refine_ls_R_factor_all          0.111
_refine_ls_R_factor_gt           0.039
_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)+(0.0398P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.081
_refine_ls_wR_factor_ref         0.093
_reflns_number_gt                2090
_reflns_number_total             4255
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at6006.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2205850
_cod_database_fobs_code          2205850
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_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_type_symbol
Cl1 -0.02175(9) 0.76906(12) 0.33706(4) 0.0735(3) Uani d . 1 Cl
S1 0.61009(7) 0.57673(10) 0.36766(3) 0.0449(2) Uani d . 1 S
S2 0.32218(7) 0.57273(10) 0.38137(3) 0.0441(2) Uani d . 1 S
S3 0.64634(7) 0.74126(10) 0.49407(3) 0.0412(2) Uani d . 1 S
S4 0.35783(7) 0.72968(10) 0.50834(3) 0.0410(2) Uani d . 1 S
S5 0.58997(8) 0.41284(13) 0.25021(4) 0.0613(3) Uani d . 1 S
S6 0.27490(8) 0.41386(12) 0.26387(3) 0.0564(3) Uani d . 1 S
S7 0.69007(8) 0.93152(11) 0.60582(3) 0.0525(2) Uani d . 1 S
S8 0.37461(7) 0.91132(11) 0.62290(3) 0.0503(2) Uani d . 1 S
O1 0.0184(4) 0.6982(5) 0.47481(18) 0.1500(16) Uani d . 1 O
O2 -0.0339(4) 0.4778(6) 0.42835(13) 0.1626(18) Uani d . 1 O
C1 0.4771(3) 0.6190(4) 0.41072(12) 0.0376(7) Uani d . 1 C
C2 0.4924(2) 0.6877(4) 0.46525(12) 0.0371(7) Uani d . 1 C
C3 0.5162(3) 0.4894(4) 0.31176(11) 0.0389(7) Uani d . 1 C
C4 0.3820(3) 0.4880(4) 0.31787(11) 0.0391(7) Uani d . 1 C
C5 0.5845(3) 0.8377(4) 0.55535(11) 0.0348(7) Uani d . 1 C
C6 0.4500(3) 0.8308(4) 0.56181(11) 0.0374(7) Uani d . 1 C
C7 0.7631(3) 0.4249(4) 0.26666(13) 0.0625(10) Uani d . 1 C
H7A 0.8128 0.3846 0.2345 0.094 Uiso calc R 1 H
H7B 0.7831 0.3567 0.2998 0.094 Uiso calc R 1 H
H7C 0.7870 0.5401 0.2746 0.094 Uiso calc R 1 H
C8 0.1231(3) 0.3760(5) 0.30084(13) 0.0649(10) Uani d . 1 C
H8A 0.0567 0.3343 0.2742 0.097 Uiso calc R 1 H
H8B 0.0925 0.4794 0.3176 0.097 Uiso calc R 1 H
H8C 0.1384 0.2938 0.3306 0.097 Uiso calc R 1 H
C9 0.8474(3) 0.9385(4) 0.57050(13) 0.0580(10) Uani d . 1 C
H9A 0.9130 0.9890 0.5956 0.087 Uiso calc R 1 H
H9B 0.8388 1.0044 0.5360 0.087 Uiso calc R 1 H
H9C 0.8746 0.8259 0.5610 0.087 Uiso calc R 1 H
C10 0.2012(3) 0.9018(5) 0.60364(14) 0.0667(11) Uani d . 1 C
H10A 0.1493 0.9437 0.6349 0.100 Uiso calc R 1 H
H10B 0.1766 0.7870 0.5956 0.100 Uiso calc R 1 H
H10C 0.1847 0.9697 0.5701 0.100 Uiso calc R 1 H
C11 -0.0038(4) 0.5488(6) 0.47230(16) 0.0704(11) Uani d . 1 C
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'
Cl Cl 0.1484 0.1585 '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_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C3 . 95.64(13) y
C1 S2 C4 . 95.55(14) y
C2 S3 C5 . 95.57(13) y
C2 S4 C6 . 95.36(13) y
C3 S5 C7 . 103.46(14) y
C4 S6 C8 . 103.27(14) y
C5 S7 C9 . 103.57(13) y
C6 S8 C10 . 102.34(14) y
C2 C1 S1 . 122.4(2) y
C2 C1 S2 . 122.0(2) y
S1 C1 S2 . 115.54(16) y
C1 C2 S3 . 122.4(2) y
C1 C2 S4 . 122.1(2) y
S3 C2 S4 . 115.45(16) y
C4 C3 S5 . 121.5(2) y
C4 C3 S1 . 116.8(2) y
S5 C3 S1 . 121.67(16) y
C3 C4 S2 . 116.3(2) y
C3 C4 S6 . 121.9(2) y
S2 C4 S6 . 121.71(16) y
C6 C5 S7 . 122.5(2) y
C6 C5 S3 . 116.1(2) y
S7 C5 S3 . 121.35(15) y
C5 C6 S4 . 117.2(2) y
C5 C6 S8 . 121.3(2) y
S4 C6 S8 . 121.41(16) y
S5 C7 H7A . 109.5 ?
S5 C7 H7B . 109.5 ?
H7A C7 H7B . 109.5 ?
S5 C7 H7C . 109.5 ?
H7A C7 H7C . 109.5 ?
H7B C7 H7C . 109.5 ?
S6 C8 H8A . 109.5 ?
S6 C8 H8B . 109.5 ?
H8A C8 H8B . 109.5 ?
S6 C8 H8C . 109.5 ?
H8A C8 H8C . 109.5 ?
H8B C8 H8C . 109.5 ?
S7 C9 H9A . 109.5 ?
S7 C9 H9B . 109.5 ?
H9A C9 H9B . 109.5 ?
S7 C9 H9C . 109.5 ?
H9A C9 H9C . 109.5 ?
H9B C9 H9C . 109.5 ?
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 ?
O2 C11 O1 . 123.0(5) ?
O2 C11 C11 3_566 119.9(6) y
O1 C11 C11 3_566 117.2(6) y
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
S1 C1 . 1.715(3) y
S1 C3 . 1.736(3) y
S2 C1 . 1.725(3) y
S2 C4 . 1.739(3) y
S3 C2 . 1.725(3) y
S3 C5 . 1.741(3) y
S4 C2 . 1.727(3) y
S4 C6 . 1.733(3) y
S5 C3 . 1.733(3) y
S5 C7 . 1.774(3) y
S6 C4 . 1.741(3) y
S6 C8 . 1.787(3) y
S7 C5 . 1.735(3) y
S7 C9 . 1.792(3) y
S8 C6 . 1.742(3) y
S8 C10 . 1.790(3) y
O1 C11 . 1.205(5) y
O2 C11 . 1.201(5) y
C1 C2 . 1.387(4) y
C3 C4 . 1.355(4) y
C5 C6 . 1.360(4) y
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C11 3_566 1.504(7) ?
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
_geom_hbond_publ_flag
C8 H8B Cl1 . 0.96 2.61 3.543(4) 165 yes
C8 H8A Cl1 2_545 0.96 2.66 3.454(3) 141 yes
C7 H7A Cl1 2_645 0.96 2.85 3.780(3) 163 yes
C9 H9A Cl1 3_676 0.96 2.69 3.594(3) 157 yes
C9 H9A Cl1 3_676 0.96 2.69 3.594(3) 157 yes
C8 H8C S7 3_666 0.96 2.87 3.744(4) 152 yes
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
C3 S1 C1 C2 177.5(3)
C3 S1 C1 S2 -3.3(2)
C4 S2 C1 C2 -177.7(2)
C4 S2 C1 S1 3.1(2)
S1 C1 C2 S3 1.5(4)
S2 C1 C2 S3 -177.72(16)
S1 C1 C2 S4 -179.92(16)
S2 C1 C2 S4 0.9(4)
C5 S3 C2 C1 173.1(2)
C5 S3 C2 S4 -5.57(19)
C6 S4 C2 C1 -173.4(2)
C6 S4 C2 S3 5.29(19)
C7 S5 C3 C4 -174.7(3)
C7 S5 C3 S1 7.1(2)
C1 S1 C3 C4 2.3(3)
C1 S1 C3 S5 -179.46(18)
S5 C3 C4 S2 -178.80(16)
S1 C3 C4 S2 -0.5(3)
S5 C3 C4 S6 -1.4(4)
S1 C3 C4 S6 176.86(16)
C1 S2 C4 C3 -1.5(3)
C1 S2 C4 S6 -178.88(19)
C8 S6 C4 C3 162.0(3)
C8 S6 C4 S2 -20.7(2)
C9 S7 C5 C6 -170.1(3)
C9 S7 C5 S3 11.7(2)
C2 S3 C5 C6 3.7(2)
C2 S3 C5 S7 -178.03(18)
S7 C5 C6 S4 -178.89(15)
S3 C5 C6 S4 -0.7(3)
S7 C5 C6 S8 -1.9(4)
S3 C5 C6 S8 176.37(15)
C2 S4 C6 C5 -2.8(3)
C2 S4 C6 S8 -179.79(18)
C10 S8 C6 C5 170.7(3)
C10 S8 C6 S4 -12.4(2)
