#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007244.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_2007244
loop_
_publ_author_name
'Rimbaud, C.'
'Le Magueres, P.'
'Ouahab, L.'
'Lorcy, D.'
'Robert, A.'
_publ_section_title
;
 1,2-Bis(5-methyl-4-methylthio-1,3-dithiolium-2-ylidene)-1,2-diphenylethane
 Bis(triiodide) and
 1,2-Bis(4-methoxyphenyl)-1,2-bis(5-methyl-4-methylthio-1,3-dithiolium-2-ylidene)ethane
 Diperchlorate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              679
_journal_page_last               681
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C26 H26 O2 S6 2+, 2Cl O4 1-'
_chemical_formula_sum            'C26 H26 Cl2 O10 S6'
_chemical_formula_weight         761.73
_chemical_name_systematic
;
 Bis(4-methoxylphenyl)-1,2-bis(5-methyl-4-methylthio-1,3-dithiolium-2-ylidene)
ethane Perchlorate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 104.32(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.087(5)
_cell_length_b                   10.4329(10)
_cell_length_c                   14.325(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      14
_cell_volume                     1605.5(13)
_computing_cell_refinement       'CAD4 Software'
_computing_data_collection       'CAD4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       \q/2\q
_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  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4029
_diffrn_reflns_theta_max         27.91
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_type   'Empirical via \y scan (North et al., 1968)'
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_meas      'Not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.288
_refine_ls_extinction_coef       0.0022(8)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.019
_refine_ls_goodness_of_fit_obs   1.053
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_restrained_S_obs      1.053
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_obs          0.0384
_refine_ls_shift/esd_max         0.032
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1096
_refine_ls_wR_factor_obs         0.0948
_reflns_number_observed          2751
_reflns_number_total             3840
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ln1043.cif
_[local]_cod_data_source_block   1b
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1605.4(13)
_cod_database_code               2007244
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0270(3) 0.0421(4) 0.0272(3) -0.0061(2) 0.0058(2) -0.0070(2)
S2 0.0280(3) 0.0460(4) 0.0278(3) -0.0061(3) 0.0077(2) -0.0022(3)
S3 0.0427(4) 0.0436(4) 0.0285(3) -0.0072(3) 0.0031(3) -0.0074(3)
C1 0.0243(10) 0.0262(11) 0.0266(11) -0.0015(9) 0.0037(8) -0.0025(9)
C2 0.0273(11) 0.0304(12) 0.0279(11) -0.0015(9) 0.0077(9) -0.0018(9)
C3 0.0344(12) 0.0297(12) 0.0241(11) -0.0001(10) 0.0059(9) -0.0023(9)
C4 0.0346(12) 0.0376(13) 0.0249(11) -0.0009(10) 0.0069(9) -0.0015(10)
C5 0.045(2) 0.080(2) 0.0329(14) -0.007(2) 0.0181(12) -0.0071(15)
C6 0.0356(15) 0.098(3) 0.055(2) -0.013(2) 0.0044(13) -0.031(2)
C7 0.0232(10) 0.0308(12) 0.0248(11) -0.0045(9) 0.0057(8) -0.0014(9)
C8 0.0254(11) 0.0302(12) 0.0376(13) 0.0018(9) 0.0067(9) 0.0035(10)
C9 0.0333(12) 0.0256(12) 0.0486(15) -0.0041(10) 0.0086(11) -0.0016(11)
C10 0.0253(11) 0.0370(14) 0.0373(13) -0.0065(10) 0.0057(9) -0.0016(10)
C11 0.0237(11) 0.0338(13) 0.0432(14) 0.0018(10) 0.0035(10) 0.0005(11)
C12 0.0321(12) 0.0252(11) 0.0364(13) -0.0008(10) 0.0059(10) -0.0014(10)
C13 0.0256(13) 0.065(2) 0.090(3) -0.0095(14) -0.0035(14) -0.002(2)
O1 0.0283(9) 0.0417(11) 0.082(2) -0.0111(8) -0.0015(9) -0.0054(10)
Cl 0.0410(4) 0.0382(4) 0.0548(4) -0.0021(3) 0.0118(3) -0.0041(3)
O2 0.075(2) 0.061(2) 0.0588(14) 0.0025(12) 0.0021(12) 0.0123(12)
O3 0.084(2) 0.084(2) 0.073(2) 0.020(2) 0.0400(15) 0.0114(15)
O4 0.0433(12) 0.069(2) 0.087(2) -0.0065(11) 0.0032(12) -0.0035(14)
O5 0.068(2) 0.0512(15) 0.133(3) -0.0140(12) 0.027(2) -0.039(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S1 0.62632(5) 0.07142(6) 0.20038(4) 0.0323(2) Uani d . 1 S
S2 0.37454(6) 0.00311(7) 0.18830(4) 0.0338(2) Uani d . 1 S
S3 0.67477(6) 0.14482(7) 0.40932(4) 0.0393(2) Uani d . 1 S
C1 0.4611(2) -0.0143(2) 0.0291(2) 0.0262(5) Uani d . 1 C
C2 0.4903(2) 0.0166(2) 0.1307(2) 0.0284(5) Uani d . 1 C
C3 0.5755(2) 0.0912(2) 0.3031(2) 0.0296(5) Uani d . 1 C
C4 0.4538(2) 0.0611(2) 0.2968(2) 0.0324(5) Uani d . 1 C
C5 0.3885(3) 0.0789(3) 0.3756(2) 0.0511(8) Uani d . 1 C
H5A 0.4283(13) 0.0275(17) 0.4301(6) 0.077 Uiso calc R 1 H
H5B 0.3031(6) 0.0531(18) 0.3531(6) 0.077 Uiso calc R 1 H
H5C 0.3921(18) 0.1675(5) 0.3942(11) 0.077 Uiso calc R 1 H
C6 0.8135(3) 0.1794(4) 0.3716(2) 0.0641(10) Uani d . 1 C
H6A 0.8443(13) 0.1021(6) 0.3494(17) 0.096 Uiso calc R 1 H
H6B 0.8753(9) 0.2137(18) 0.4249(6) 0.096 Uiso calc R 1 H
H6C 0.7953(6) 0.2410(18) 0.3202(13) 0.096 Uiso calc R 1 H
C7 0.3391(2) -0.0805(2) -0.0089(2) 0.0263(5) Uani d . 1 C
C8 0.3340(2) -0.2139(2) -0.0130(2) 0.0312(5) Uani d . 1 C
H8 0.4059(2) -0.2618(2) 0.0100(2) 0.037 Uiso calc R 1 H
C9 0.2225(2) -0.2747(2) -0.0511(2) 0.0361(6) Uani d . 1 C
H9 0.2195(2) -0.3637(2) -0.0541(2) 0.043 Uiso calc R 1 H
C10 0.1145(2) -0.2042(2) -0.0851(2) 0.0336(5) Uani d . 1 C
C11 0.1177(2) -0.0708(2) -0.0804(2) 0.0344(5) Uani d . 1 C
H11 0.0454(2) -0.0231(2) -0.1026(2) 0.041 Uiso calc R 1 H
C12 0.2301(2) -0.0106(2) -0.0421(2) 0.0317(5) Uani d . 1 C
H12 0.2330(2) 0.0784(2) -0.0384(2) 0.038 Uiso calc R 1 H
C13 -0.1048(3) -0.2072(3) -0.1531(3) 0.0634(10) Uani d . 1 C
H13A -0.1719(4) -0.2676(3) -0.1709(18) 0.095 Uiso calc R 1 H
H13B -0.1020(10) -0.1552(18) -0.2078(12) 0.095 Uiso calc R 1 H
H13C -0.1179(12) -0.1535(18) -0.1020(7) 0.095 Uiso calc R 1 H
O1 0.0098(2) -0.2743(2) -0.1212(2) 0.0533(6) Uani d . 1 O
Cl 0.94548(6) 0.10232(7) 0.67378(5) 0.0447(2) Uani d . 1 Cl
O2 0.9014(2) 0.2061(2) 0.6082(2) 0.0675(7) Uani d . 1 O
O3 0.8842(3) 0.1096(3) 0.7503(2) 0.0770(8) Uani d . 1 O
O4 1.0767(2) 0.1145(2) 0.7117(2) 0.0687(7) Uani d . 1 O
O5 0.9182(2) -0.0174(2) 0.6263(2) 0.0837(9) Uani d . 1 O
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'
Cl Cl 0.1484 0.1585 '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'
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
_geom_angle_publ_flag
C2 S1 C3 . 96.50(12) yes
C2 S2 C4 . 97.66(12) yes
C3 S3 C6 . 101.94(13) yes
C1 C1 C2 3_655 123.0(3) no
C1 C1 C7 3_655 121.8(2) no
C2 C1 C7 . 115.2(2) yes
C1 C2 S1 . 127.9(2) yes
C1 C2 S2 . 117.6(2) yes
S1 C2 S2 . 114.40(14) yes
C4 C3 S1 . 116.4(2) yes
C4 C3 S3 . 122.3(2) yes
S1 C3 S3 . 121.30(14) yes
C3 C4 C5 . 125.1(2) yes
C3 C4 S2 . 115.0(2) yes
C5 C4 S2 . 119.9(2) yes
C4 C5 H5A . 109.5 no
C4 C5 H5B . 109.47 no
H5A C5 H5B . 109.5 no
C4 C5 H5C . 109.5 no
H5A C5 H5C . 109.5 no
H5B C5 H5C . 109.5 no
S3 C6 H6A . 109.47 no
S3 C6 H6B . 109.47 no
H6A C6 H6B . 109.5 no
S3 C6 H6C . 109.47 no
H6A C6 H6C . 109.5 no
H6B C6 H6C . 109.5 no
C12 C7 C8 . 119.1(2) no
C12 C7 C1 . 120.9(2) no
C8 C7 C1 . 120.0(2) no
C9 C8 C7 . 120.0(2) no
C9 C8 H8 . 119.99 no
C7 C8 H8 . 119.99 no
C8 C9 C10 . 120.5(2) no
C8 C9 H9 . 119.75 no
C10 C9 H9 . 119.75 no
O1 C10 C9 . 115.4(2) no
O1 C10 C11 . 124.4(2) no
C9 C10 C11 . 120.2(2) no
C12 C11 C10 . 118.9(2) no
C12 C11 H11 . 120.57 no
C10 C11 H11 . 120.57 no
C11 C12 C7 . 121.3(2) no
C11 C12 H12 . 119.35 no
C7 C12 H12 . 119.35 no
O1 C13 H13A . 109.5 no
O1 C13 H13B . 109.5 no
H13A C13 H13B . 109.5 no
O1 C13 H13C . 109.5 no
H13A C13 H13C . 109.5 no
H13B C13 H13C . 109.5 no
C10 O1 C13 . 117.8(2) no
O5 Cl O4 . 109.7(2) no
O5 Cl O3 . 109.2(2) no
O4 Cl O3 . 109.7(2) no
O5 Cl O2 . 110.6(2) no
O4 Cl O2 . 109.3(2) no
O3 Cl O2 . 108.2(2) no
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 C2 . 1.689(2) yes
S1 C3 . 1.714(2) yes
S2 C2 . 1.695(2) yes
S2 C4 . 1.696(3) yes
S3 C3 . 1.735(2) yes
S3 C6 . 1.788(3) yes
C1 C1 3_655 1.371(4) no
C1 C2 . 1.447(3) yes
C1 C7 . 1.496(3) yes
C3 C4 . 1.366(3) yes
C4 C5 . 1.497(3) yes
C5 H5A . 0.96 no
C5 H5B . 0.96 no
C5 H5C . 0.96 no
C6 H6A . 0.96 no
C6 H6B . 0.96 no
C6 H6C . 0.96 no
C7 C12 . 1.391(3) no
C7 C8 . 1.393(3) no
C8 C9 . 1.377(3) no
C8 H8 . 0.93 no
C9 C10 . 1.387(3) no
C9 H9 . 0.93 no
C10 O1 . 1.362(3) no
C10 C11 . 1.393(4) no
C11 C12 . 1.382(3) no
C11 H11 . 0.93 no
C12 H12 . 0.93 no
C13 O1 . 1.423(4) no
C13 H13A . 0.96 no
C13 H13B . 0.96 no
C13 H13C . 0.96 no
Cl O5 . 1.419(2) no
Cl O4 . 1.427(2) no
Cl O3 . 1.428(3) no
Cl O2 . 1.437(2) no