#------------------------------------------------------------------------------ #$Date: 2025-08-19 20:30:04 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301811 $ #$URL: svn://www.crystallography.net/cod/cif/4/00/04/4000473.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4000473 loop_ _publ_author_name 'Noh, Dong-Youn' 'Willing, Gerold A.' 'Han, Catherine Y.' 'Shin, Kyong-Soon' 'Geiser, Urs' 'Wang, H. Hau' _publ_section_title ; BEDT-TTF template crystallization with use of an electron donor molecule with dodecanethiol ; _journal_name_full 'Chemistry of Materials' _journal_paper_doi 10.1021/cm049660j _journal_year 2004 _chemical_formula_moiety 'C21 H31 Br S8' _chemical_formula_sum 'C21 H31 Br S8' _chemical_formula_weight 619.85 _chemical_name_systematic ; 3-(12-bromododecyl)thio-4-methylthio-3',4'-ethylenedithio-tetrathiafulvalene ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 101.676(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.3989(4) _cell_length_b 48.565(4) _cell_length_c 10.5256(9) _cell_measurement_reflns_used 1374 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 23.34 _cell_measurement_theta_min 2.59 _cell_volume 2702.7(4) _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 8.192 _diffrn_measurement_device_type 'CCD area detector diffractometer' _diffrn_measurement_method '0.3 deg \w-scans' _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 0.0793 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_k_min -51 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 10142 _diffrn_reflns_theta_max 21.97 _diffrn_reflns_theta_min 1.68 _diffrn_standards_decay_% 0.0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _exptl_absorpt_coefficient_mu 2.149 _exptl_absorpt_correction_T_max 0.86 _exptl_absorpt_correction_T_min 0.44 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; The absorption correction was based on a series expansion of spherical harmonics to minimize the intensity variance of replicate reflections with program SADABS (Sheldrick 1997) ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1280 _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.02 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.229 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 3307 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.229 _refine_ls_R_factor_all 0.1178 _refine_ls_R_factor_gt 0.0963 _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^)+(0.0625P)^2^+30.2333P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2109 _refine_ls_wR_factor_ref 0.2198 _reflns_number_gt 2694 _reflns_number_total 3307 _reflns_threshold_expression >2sigma(I) _cod_original_sg_symbol_H-M P2(1)/n _cod_database_code 4000473 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_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 1.4356(3) 0.38653(3) -0.07322(14) 0.0554(5) Uani 1 1 d . . . S1 S -1.2776(7) 0.70537(7) 0.2257(3) 0.0511(10) Uani 1 1 d . . . S2 S -0.9754(7) 0.67453(6) 0.0741(3) 0.0452(9) Uani 1 1 d . . . S3 S -1.0636(7) 0.66771(6) 0.4794(3) 0.0405(9) Uani 1 1 d . . . S4 S -0.7627(7) 0.63574(6) 0.3250(3) 0.0430(9) Uani 1 1 d . . . S5 S -1.2952(8) 0.75719(7) 0.0765(4) 0.0534(10) Uani 1 1 d . . . S6 S -0.9635(8) 0.71877(8) -0.1185(4) 0.0583(11) Uani 1 1 d . . . S7 S -0.7937(7) 0.64307(7) 0.7335(3) 0.0442(9) Uani 1 1 d . . . S8 S -0.4722(7) 0.60597(6) 0.5626(3) 0.0421(9) Uani 1 1 d . . . C1 C -1.064(2) 0.6785(2) 0.2238(12) 0.038(3) Uani 1 1 d . . . C2 C -0.967(2) 0.6629(2) 0.3289(11) 0.034(3) Uani 1 1 d . . . C3 C -1.184(2) 0.7231(2) 0.0973(12) 0.038(3) Uani 1 1 d . . . C4 C -1.052(3) 0.7085(2) 0.0278(12) 0.044(4) Uani 1 1 d . . . C5 C -0.830(2) 0.6454(2) 0.5660(10) 0.031(3) Uani 1 1 d . . . C6 C -0.696(2) 0.6305(2) 0.4945(10) 0.030(3) Uani 1 1 d . . . C7 C -1.177(3) 0.7670(3) -0.0629(14) 0.062(4) Uani 1 1 d . . . H7A H -1.2691 0.7832 -0.1009 0.074 Uiso 1 1 calc R . . H7B H -1.0009 0.7724 -0.0352 0.074 Uiso 1 1 calc R . . C8 C -1.193(3) 0.7454(3) -0.1663(12) 0.052(4) Uani 1 1 d . . . H8A H -1.1664 0.7539 -0.2459 0.062 Uiso 1 1 calc R . . H8B H -1.3615 0.7374 -0.1834 0.062 Uiso 1 1 calc R . . C9 C -0.544(3) 0.6679(3) 0.7822(13) 0.060(4) Uani 1 1 d . . . H9A H -0.5015 0.6688 0.8751 0.091 Uiso 1 1 calc R . . H9B H -0.5999 0.6856 0.7477 0.091 Uiso 1 1 calc R . . H9C H -0.3980 0.6623 0.7496 0.091 Uiso 1 1 calc R . . C10 C -0.351(2) 0.5939(2) 0.4250(11) 0.037(3) Uani 1 1 d . . . H10A H -0.4896 0.5869 0.3592 0.044 Uiso 1 1 calc R . . H10B H -0.2726 0.6090 0.3879 0.044 Uiso 1 1 calc R . . C11 C -0.160(2) 0.5713(2) 0.4665(11) 0.035(3) Uani 1 1 d . . . H11A H -0.2391 0.5564 0.5057 0.042 Uiso 1 1 calc R . . H11B H -0.0216 0.5784 0.5314 0.042 Uiso 1 1 calc R . . C12 C -0.056(2) 0.5599(2) 0.3509(12) 0.038(3) Uani 1 1 d . . . H12A H -0.1968 0.5537 0.2844 0.045 Uiso 1 1 calc R . . H12B H 0.0281 0.5747 0.3144 0.045 Uiso 1 1 calc R . . C13 C 0.127(2) 0.5363(2) 0.3875(13) 0.040(3) Uani 1 1 d . . . H13A H 0.0416 0.5213 0.4212 0.047 Uiso 1 1 calc R . . H13B H 0.2654 0.5423 0.4559 0.047 Uiso 1 1 calc R . . C14 C 0.235(2) 0.5259(2) 0.2728(12) 0.036(3) Uani 1 1 d . . . H14A H 0.0956 0.5204 0.2040 0.043 Uiso 1 1 calc R . . H14B H 0.3219 0.5410 0.2402 0.043 Uiso 1 1 calc R . . C15 C 0.415(2) 0.5022(3) 0.3024(12) 0.042(3) Uani 1 1 d . . . H15A H 0.3282 0.4870 0.3350 0.051 Uiso 1 1 calc R . . H15B H 0.5545 0.5076 0.3711 0.051 Uiso 1 1 calc R . . C16 C 0.522(2) 0.4918(2) 0.1885(11) 0.038(3) Uani 1 1 d . . . H16A H 0.3828 0.4864 0.1194 0.046 Uiso 1 1 calc R . . H16B H 0.6102 0.5068 0.1562 0.046 Uiso 1 1 calc R . . C17 C 0.701(3) 0.4678(3) 0.2200(13) 0.046(4) Uani 1 1 d . . . H17A H 0.6113 0.4526 0.2493 0.056 Uiso 1 1 calc R . . H17B H 0.8371 0.4730 0.2912 0.056 Uiso 1 1 calc R . . C18 C 0.817(2) 0.4579(2) 0.1071(12) 0.041(3) Uani 1 1 d . . . H18A H 0.9136 0.4729 0.0797 0.049 Uiso 1 1 calc R . . H18B H 0.6823 0.4532 0.0346 0.049 Uiso 1 1 calc R . . C19 C 0.991(3) 0.4329(3) 0.1418(12) 0.045(3) Uani 1 1 d . . . H19A H 1.1260 0.4376 0.2141 0.054 Uiso 1 1 calc R . . H19B H 0.8946 0.4180 0.1692 0.054 Uiso 1 1 calc R . . C20 C 1.104(2) 0.4232(2) 0.0295(12) 0.037(3) Uani 1 1 d . . . H20A H 0.9698 0.4187 -0.0436 0.044 Uiso 1 1 calc R . . H20B H 1.2043 0.4379 0.0030 0.044 Uiso 1 1 calc R . . C21 C 1.268(3) 0.3984(3) 0.0658(12) 0.048(4) Uani 1 1 d . . . H21A H 1.1657 0.3835 0.0876 0.058 Uiso 1 1 calc R . . H21B H 1.3960 0.4027 0.1424 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0657(11) 0.0558(9) 0.0496(9) -0.0066(7) 0.0236(7) 0.0179(8) S1 0.060(3) 0.042(2) 0.056(2) 0.0179(17) 0.0238(19) 0.0262(18) S2 0.065(3) 0.0287(18) 0.0407(19) 0.0003(15) 0.0089(17) 0.0121(17) S3 0.050(2) 0.0304(18) 0.0442(19) 0.0069(14) 0.0167(17) 0.0144(15) S4 0.060(2) 0.0352(18) 0.0333(18) 0.0036(14) 0.0079(16) 0.0218(17) S5 0.078(3) 0.0324(19) 0.053(2) 0.0077(16) 0.021(2) 0.0190(19) S6 0.077(3) 0.053(2) 0.053(2) 0.0100(18) 0.030(2) 0.019(2) S7 0.059(2) 0.040(2) 0.0361(18) 0.0037(15) 0.0163(17) 0.0097(17) S8 0.054(2) 0.0384(19) 0.0355(18) 0.0060(14) 0.0130(16) 0.0228(16) C1 0.041(8) 0.026(7) 0.043(8) 0.004(6) -0.001(6) 0.008(6) C2 0.036(8) 0.027(7) 0.040(7) -0.003(6) 0.007(6) 0.010(6) C3 0.051(9) 0.025(7) 0.040(7) 0.009(6) 0.010(6) 0.005(6) C4 0.071(10) 0.020(7) 0.038(7) 0.009(6) 0.007(7) 0.015(7) C5 0.045(8) 0.030(7) 0.018(6) 0.000(5) 0.006(6) 0.007(6) C6 0.040(8) 0.025(6) 0.022(6) 0.008(5) 0.004(6) 0.012(6) C7 0.087(12) 0.038(8) 0.067(10) 0.011(7) 0.032(9) 0.020(8) C8 0.065(11) 0.050(9) 0.037(8) 0.015(7) 0.006(7) 0.011(8) C9 0.073(11) 0.060(10) 0.045(8) -0.012(7) 0.005(8) -0.004(8) C10 0.053(9) 0.032(7) 0.029(6) 0.003(5) 0.019(6) 0.005(6) C11 0.037(8) 0.028(7) 0.038(7) 0.009(5) 0.006(6) 0.022(6) C12 0.044(8) 0.023(7) 0.048(8) 0.001(6) 0.011(6) 0.012(6) C13 0.034(8) 0.026(7) 0.059(8) 0.020(6) 0.012(7) 0.011(6) C14 0.039(8) 0.022(7) 0.050(8) -0.005(6) 0.013(6) 0.009(6) C15 0.038(8) 0.031(7) 0.057(8) 0.002(6) 0.010(7) 0.012(6) C16 0.050(9) 0.026(7) 0.040(7) -0.004(6) 0.013(6) 0.007(6) C17 0.058(10) 0.031(7) 0.053(8) 0.004(6) 0.018(7) 0.016(7) C18 0.042(8) 0.028(7) 0.054(8) 0.003(6) 0.014(7) 0.015(6) C19 0.054(9) 0.041(8) 0.041(8) -0.008(6) 0.013(7) 0.010(7) C20 0.042(8) 0.028(7) 0.041(7) 0.003(6) 0.007(6) 0.005(6) C21 0.059(10) 0.050(8) 0.040(8) 0.003(6) 0.024(7) 0.031(7) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 101365881