#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/49/2104962.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_2104962 loop_ _publ_author_name 'Garc\'ia-Ordu\~na, Pilar' 'Dahaoui, Slimane' 'Lecomte, Claude' _publ_section_title ; Intermolecular interactions and charge transfer in the 2:1 tetrathiafulvalene bromanil complex, (TTF)~2~-BA ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 244 _journal_page_last 249 _journal_paper_doi 10.1107/S0108768111015801 _journal_volume 67 _journal_year 2011 _chemical_formula_iupac '2(C6 H4 S4),( C6 Br4 O2)' _chemical_formula_moiety '2(C6 H4 S4),(C6 Br4 O2)' _chemical_formula_structural '(C6 H4 S4)2,(C6 Br4 O2)' _chemical_formula_sum 'C18 H8 Br4 O2 S8' _chemical_formula_weight 832.40 _chemical_name_common 'bis-tetrathiafulvalene p-bromanil' _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 110.434(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 10.2781(9) _cell_length_b 11.5982(8) _cell_length_c 11.0418(9) _cell_measurement_reflns_used 51302 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 31.12 _cell_measurement_theta_min 3.36 _cell_volume 1233.44(18) _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD (Nonius, 1998) ' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEPIII (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device Xcalibur-Saphire2 _diffrn_measurement_method \f _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 0.0587 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 51302 _diffrn_reflns_theta_full 31.12 _diffrn_reflns_theta_max 31.12 _diffrn_reflns_theta_min 3.36 _exptl_absorpt_coefficient_mu 7.221 _exptl_absorpt_correction_T_max 0.282 _exptl_absorpt_correction_T_min 0.086 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'Absorb, (DeTitta, 1985)' _exptl_crystal_colour black _exptl_crystal_density_diffrn 2.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _refine_diff_density_max 1.307 _refine_diff_density_min -0.703 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 3761 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.124 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0330 _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/[\s^2^(Fo^2^)+(0.0599P)^2^+0.3946P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0826 _refine_ls_wR_factor_ref 0.0831 _reflns_number_gt 3905 _reflns_number_total 3972 _reflns_threshold_expression >2sigma(I) _cod_data_source_file gw5013.cif _cod_data_source_block 100K _cod_original_cell_volume 1233.44(17) _cod_original_sg_symbol_Hall '-p 2yn' _cod_original_sg_symbol_H-M 'p 21/n ' _cod_database_code 2104962 _cod_database_fobs_code 2104962 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_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_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.32390(17) 0.00682(15) -0.24724(16) 0.0218(3) Uani d . 1 1 . . Br Br1 0.19466(2) -0.13098(2) -0.08665(2) 0.02120(7) Uani d . 1 1 . . Br Br2 0.42377(2) -0.152668(18) 0.21952(2) 0.01911(7) Uani d . 1 1 . . C C1 0.4028(2) 0.00561(18) -0.1342(2) 0.0173(3) Uani d . 1 1 . . C C2 0.3688(2) -0.05780(18) -0.0314(2) 0.0172(3) Uani d . 1 1 . . C C3 0.4598(2) -0.06521(17) 0.0919(2) 0.0168(3) Uani d . 1 1 . . C C8 0.4030(2) 0.21988(18) 0.1589(2) 0.0170(3) Uani d . 1 1 . . C C11 0.3511(2) 0.15768(19) 0.2361(2) 0.0180(4) Uani d . 1 1 . . S S1 0.30860(6) 0.23785(5) -0.00639(5) 0.01955(11) Uani d . 1 1 . . S S2 0.56075(5) 0.29656(5) 0.21720(5) 0.01841(10) Uani d . 1 1 . . S S3 0.43916(6) 0.14075(5) 0.40332(5) 0.02055(11) Uani d . 1 1 . . S S4 0.18647(6) 0.09187(5) 0.17688(5) 0.02073(11) Uani d . 1 1 . . C C7 0.4274(3) 0.3335(2) -0.0334(2) 0.0217(4) Uani d . 1 1 . . H H7 0.4112 0.3666 -0.1160 0.026 Uiso calc R 1 1 . . C C9 0.5425(3) 0.35789(19) 0.0678(2) 0.0209(4) Uani d . 1 1 . . H H9 0.6121 0.4072 0.0583 0.025 Uiso calc R 1 1 . . C C10 0.3074(3) 0.0619(2) 0.4299(2) 0.0241(4) Uani d . 1 1 . . H H10 0.3161 0.0362 0.5141 0.029 Uiso calc R 1 1 . . C C12 0.1927(3) 0.0388(2) 0.3270(2) 0.0240(4) Uani d . 1 1 . . H H12 0.1181 -0.0046 0.3357 0.029 Uiso calc R 1 1 . . 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 O1 0.0208(7) 0.0249(8) 0.0162(7) -0.0025(6) 0.0021(6) 0.0004(6) Br1 0.01761(11) 0.02410(12) 0.02058(11) -0.00495(7) 0.00502(8) -0.00094(7) Br2 0.02177(11) 0.01867(11) 0.01796(11) 0.00007(7) 0.00829(8) 0.00280(7) C1 0.0182(8) 0.0167(8) 0.0167(8) -0.0012(7) 0.0058(7) -0.0005(6) C2 0.0162(8) 0.0164(8) 0.0179(8) -0.0027(7) 0.0045(7) -0.0002(7) C3 0.0175(8) 0.0153(8) 0.0173(8) -0.0011(6) 0.0059(7) 0.0009(6) C8 0.0155(8) 0.0187(8) 0.0154(8) 0.0002(7) 0.0037(6) -0.0005(7) C11 0.0182(9) 0.0194(9) 0.0164(8) 0.0009(7) 0.0059(7) -0.0009(7) S1 0.0184(2) 0.0221(2) 0.0153(2) 0.00063(17) 0.00225(17) -0.00021(17) S2 0.0174(2) 0.0198(2) 0.0161(2) -0.00102(17) 0.00351(17) 0.00056(16) S3 0.0214(2) 0.0240(2) 0.0164(2) 0.00058(18) 0.00676(18) 0.00183(17) S4 0.0184(2) 0.0213(2) 0.0229(2) -0.00219(18) 0.00781(18) -0.00280(18) C7 0.0267(10) 0.0219(9) 0.0164(9) 0.0017(8) 0.0075(8) 0.0014(7) C9 0.0242(10) 0.0200(9) 0.0199(9) 0.0000(7) 0.0092(8) 0.0012(7) C10 0.0286(11) 0.0236(10) 0.0247(10) 0.0031(8) 0.0152(9) 0.0047(8) C12 0.0251(10) 0.0207(9) 0.0311(11) 0.0018(8) 0.0158(9) 0.0040(8) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 O1 C1 C2 . . 122.12(19) ? O1 C1 C3 . 3_655 121.97(19) ? C2 C1 C3 . 3_655 115.89(17) ? C3 C2 C1 . . 122.08(18) ? C3 C2 Br1 . . 122.77(16) ? C1 C2 Br1 . . 115.12(14) ? C2 C3 C1 . 3_655 121.97(18) ? C2 C3 Br2 . . 122.65(16) ? C1 C3 Br2 3_655 . 115.37(14) ? C11 C8 S1 . . 121.32(16) ? C11 C8 S2 . . 123.42(16) ? S1 C8 S2 . . 115.09(12) ? C8 C11 S4 . . 122.23(17) ? C8 C11 S3 . . 123.10(17) ? S4 C11 S3 . . 114.63(12) ? C7 S1 C8 . . 95.00(10) ? C9 S2 C8 . . 94.52(11) ? C10 S3 C11 . . 95.17(11) ? C12 S4 C11 . . 95.05(11) ? C9 C7 S1 . . 117.14(17) ? C9 C7 H7 . . 121.4 ? S1 C7 H7 . . 121.4 ? C7 C9 S2 . . 118.21(18) ? C7 C9 H9 . . 120.9 ? S2 C9 H9 . . 120.9 ? C12 C10 S3 . . 117.69(18) ? C12 C10 H10 . . 121.2 ? S3 C10 H10 . . 121.2 ? C10 C12 S4 . . 117.46(18) ? C10 C12 H12 . . 121.3 ? S4 C12 H12 . . 121.3 ? 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 O1 C1 . 1.229(3) ? Br1 C2 . 1.880(2) ? Br2 C3 . 1.876(2) ? C1 C2 . 1.493(3) ? C1 C3 3_655 1.493(3) ? C2 C3 . 1.358(3) ? C3 C1 3_655 1.493(3) ? C8 C11 . 1.360(3) ? C8 S1 . 1.755(2) ? C8 S2 . 1.763(2) ? C11 S4 . 1.761(2) ? C11 S3 . 1.761(2) ? S1 C7 . 1.750(2) ? S2 C9 . 1.746(2) ? S3 C10 . 1.742(3) ? S4 C12 . 1.748(3) ? C7 C9 . 1.344(3) ? C7 H7 . 0.9500 ? C9 H9 . 0.9500 ? C10 C12 . 1.348(4) ? C10 H10 . 0.9500 ? C12 H12 . 0.9500 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C1 C2 C3 . . . . 175.7(2) ? C3 C1 C2 C3 3_655 . . . -2.8(3) ? O1 C1 C2 Br1 . . . . -2.0(3) ? C3 C1 C2 Br1 3_655 . . . 179.46(14) ? C1 C2 C3 C1 . . . 3_655 3.0(3) ? Br1 C2 C3 C1 . . . 3_655 -179.46(15) ? C1 C2 C3 Br2 . . . . -175.80(16) ? Br1 C2 C3 Br2 . . . . 1.7(3) ? S1 C8 C11 S4 . . . . -0.4(3) ? S2 C8 C11 S4 . . . . 174.65(12) ? S1 C8 C11 S3 . . . . -177.99(12) ? S2 C8 C11 S3 . . . . -2.9(3) ? C11 C8 S1 C7 . . . . 174.49(19) ? S2 C8 S1 C7 . . . . -0.94(14) ? C11 C8 S2 C9 . . . . -175.2(2) ? S1 C8 S2 C9 . . . . 0.11(14) ? C8 C11 S3 C10 . . . . 177.0(2) ? S4 C11 S3 C10 . . . . -0.76(14) ? C8 C11 S4 C12 . . . . -177.3(2) ? S3 C11 S4 C12 . . . . 0.44(14) ? C8 S1 C7 C9 . . . . 1.8(2) ? S1 C7 C9 S2 . . . . -2.1(3) ? C8 S2 C9 C7 . . . . 1.2(2) ? C11 S3 C10 C12 . . . . 0.9(2) ? S3 C10 C12 S4 . . . . -0.8(3) ? C11 S4 C12 C10 . . . . 0.2(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139064038