#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/72/2007244.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, Christian' 'Le Magueres, Pierre' 'Ouahab, Lahcene' 'Lorcy, Dominique' 'Robert, Albert' _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_paper_doi 10.1107/S010827019701768X _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 ? _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 .0384 _refine_ls_shift/esd_max 0.032 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1096 _refine_ls_wR_factor_obs .0948 _reflns_number_observed 2751 _reflns_number_total 3840 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ln1043.cif _cod_data_source_block 1b _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_enum 1527 2010-12-29 10:47:43Z saulius 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 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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1605.4(13) _cod_original_sg_symbol_H-M 'P 21/n' _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 .0270(3) .0421(4) .0272(3) -.0061(2) .0058(2) -.0070(2) S2 .0280(3) .0460(4) .0278(3) -.0061(3) .0077(2) -.0022(3) S3 .0427(4) .0436(4) .0285(3) -.0072(3) .0031(3) -.0074(3) C1 .0243(10) .0262(11) .0266(11) -.0015(9) .0037(8) -.0025(9) C2 .0273(11) .0304(12) .0279(11) -.0015(9) .0077(9) -.0018(9) C3 .0344(12) .0297(12) .0241(11) -.0001(10) .0059(9) -.0023(9) C4 .0346(12) .0376(13) .0249(11) -.0009(10) .0069(9) -.0015(10) C5 .045(2) .080(2) .0329(14) -.007(2) .0181(12) -.0071(15) C6 .0356(15) .098(3) .055(2) -.013(2) .0044(13) -.031(2) C7 .0232(10) .0308(12) .0248(11) -.0045(9) .0057(8) -.0014(9) C8 .0254(11) .0302(12) .0376(13) .0018(9) .0067(9) .0035(10) C9 .0333(12) .0256(12) .0486(15) -.0041(10) .0086(11) -.0016(11) C10 .0253(11) .0370(14) .0373(13) -.0065(10) .0057(9) -.0016(10) C11 .0237(11) .0338(13) .0432(14) .0018(10) .0035(10) .0005(11) C12 .0321(12) .0252(11) .0364(13) -.0008(10) .0059(10) -.0014(10) C13 .0256(13) .065(2) .090(3) -.0095(14) -.0035(14) -.002(2) O1 .0283(9) .0417(11) .082(2) -.0111(8) -.0015(9) -.0054(10) Cl .0410(4) .0382(4) .0548(4) -.0021(3) .0118(3) -.0041(3) O2 .075(2) .061(2) .0588(14) .0025(12) .0021(12) .0123(12) O3 .084(2) .084(2) .073(2) .020(2) .0400(15) .0114(15) O4 .0433(12) .069(2) .087(2) -.0065(11) .0032(12) -.0035(14) O5 .068(2) .0512(15) .133(3) -.0140(12) .027(2) -.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_disorder_group _atom_site_type_symbol S1 .62632(5) .07142(6) .20038(4) .0323(2) Uani d . 1 . S S2 .37454(6) .00311(7) .18830(4) .0338(2) Uani d . 1 . S S3 .67477(6) .14482(7) .40932(4) .0393(2) Uani d . 1 . S C1 .4611(2) -.0143(2) .0291(2) .0262(5) Uani d . 1 . C C2 .4903(2) .0166(2) .1307(2) .0284(5) Uani d . 1 . C C3 .5755(2) .0912(2) .3031(2) .0296(5) Uani d . 1 . C C4 .4538(2) .0611(2) .2968(2) .0324(5) Uani d . 1 . C C5 .3885(3) .0789(3) .3756(2) .0511(8) Uani d . 1 . C H5A .4283(13) .0275(17) .4301(6) .077 Uiso calc R 1 . H H5B .3031(6) .0531(18) .3531(6) .077 Uiso calc R 1 . H H5C .3921(18) .1675(5) .3942(11) .077 Uiso calc R 1 . H C6 .8135(3) .1794(4) .3716(2) .0641(10) Uani d . 1 . C H6A .8443(13) .1021(6) .3494(17) .096 Uiso calc R 1 . H H6B .8753(9) .2137(18) .4249(6) .096 Uiso calc R 1 . H H6C .7953(6) .2410(18) .3202(13) .096 Uiso calc R 1 . H C7 .3391(2) -.0805(2) -.0089(2) .0263(5) Uani d . 1 . C C8 .3340(2) -.2139(2) -.0130(2) .0312(5) Uani d . 1 . C H8 .4059(2) -.2618(2) .0100(2) .037 Uiso calc R 1 . H C9 .2225(2) -.2747(2) -.0511(2) .0361(6) Uani d . 1 . C H9 .2195(2) -.3637(2) -.0541(2) .043 Uiso calc R 1 . H C10 .1145(2) -.2042(2) -.0851(2) .0336(5) Uani d . 1 . C C11 .1177(2) -.0708(2) -.0804(2) .0344(5) Uani d . 1 . C H11 .0454(2) -.0231(2) -.1026(2) .041 Uiso calc R 1 . H C12 .2301(2) -.0106(2) -.0421(2) .0317(5) Uani d . 1 . C H12 .2330(2) .0784(2) -.0384(2) .038 Uiso calc R 1 . H C13 -.1048(3) -.2072(3) -.1531(3) .0634(10) Uani d . 1 . C H13A -.1719(4) -.2676(3) -.1709(18) .095 Uiso calc R 1 . H H13B -.1020(10) -.1552(18) -.2078(12) .095 Uiso calc R 1 . H H13C -.1179(12) -.1535(18) -.1020(7) .095 Uiso calc R 1 . H O1 .0098(2) -.2743(2) -.1212(2) .0533(6) Uani d . 1 . O Cl .94548(6) .10232(7) .67378(5) .0447(2) Uani d . 1 . Cl O2 .9014(2) .2061(2) .6082(2) .0675(7) Uani d . 1 . O O3 .8842(3) .1096(3) .7503(2) .0770(8) Uani d . 1 . O O4 1.0767(2) .1145(2) .7117(2) .0687(7) Uani d . 1 . O O5 .9182(2) -.0174(2) .6263(2) .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 . .96 no C5 H5B . .96 no C5 H5C . .96 no C6 H6A . .96 no C6 H6B . .96 no C6 H6C . .96 no C7 C12 . 1.391(3) no C7 C8 . 1.393(3) no C8 C9 . 1.377(3) no C8 H8 . .93 no C9 C10 . 1.387(3) no C9 H9 . .93 no C10 O1 . 1.362(3) no C10 C11 . 1.393(4) no C11 C12 . 1.382(3) no C11 H11 . .93 no C12 H12 . .93 no C13 O1 . 1.423(4) no C13 H13A . .96 no C13 H13B . .96 no C13 H13C . .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 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139056001