#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202104.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_2202104 loop_ _publ_author_name 'Tomura, Masaaki' 'Yamashita, Yoshiro' _publ_section_title ; An unsymmetrical tetrathiafulvalene with a fused 1,2,5-thiadiazole ring and an ethylenedioxy group ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o145 _journal_page_last o147 _journal_paper_doi 10.1107/S1600536802023723 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C8 H4 N2 O2 S5' _chemical_formula_sum 'C8 H4 N2 O2 S5' _chemical_formula_weight 320.43 _chemical_name_common ; 4,5-ethylenedioxy[1,2,5]thiadiazolotetrathiafulvalene ; _chemical_name_systematic ; 5-(4,5-ethylenedioxy-1,3-dithiol-2-ylidene)-1,3,2,4,6-diazatrithiapentalene ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 21.7363(10) _cell_length_b 12.9552(6) _cell_length_c 3.9938(5) _cell_measurement_reflns_used 18 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 42.66 _cell_measurement_theta_min 14.11 _cell_volume 1124.65(16) _computing_cell_refinement 'CAD4 Express Software' _computing_data_collection 'CAD4 Express Software (Enraf-Nonius, 1992)' _computing_data_reduction ; teXsan (Molecular Structure Corporation/Rigaku Corporation, 2000) ; _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.001 _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1271 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_number 1303 _diffrn_reflns_theta_full 74.15 _diffrn_reflns_theta_max 74.15 _diffrn_reflns_theta_min 3.97 _diffrn_standards_decay_% 0.40 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 9.434 _exptl_absorpt_correction_T_max 0.8337 _exptl_absorpt_correction_T_min 0.1164 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.892 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.611 _refine_diff_density_min -0.867 _refine_ls_abs_structure_details '(Flack, 1983)' _refine_ls_abs_structure_Flack 0.03(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 1303 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.1509 _refine_ls_R_factor_gt 0.0631 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; calc w = 1/[\s^2^(Fo^2^)+(0.0859P)^2^] where P = (Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1416 _refine_ls_wR_factor_ref 0.1735 _reflns_number_gt 791 _reflns_number_total 1303 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6206.cif _cod_data_source_block I _cod_database_code 2202104 _cod_database_fobs_code 2202104 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 0.30528(12) 0.8612(2) 0.1225(12) 0.0400(10) Uani d . 1 . . S S2 0.37929(13) 1.0282(2) -0.2161(11) 0.0361(8) Uani d . 1 . . S S3 0.42294(13) 0.7100(2) 0.0777(11) 0.0372(8) Uani d . 1 . . S S4 0.49339(12) 0.8760(2) -0.2692(10) 0.0339(9) Uani d . 1 . . S S5 0.21400(13) 1.1375(2) 0.1239(13) 0.0450(10) Uani d . 1 . . S O1 0.5248(4) 0.5955(6) 0.089(4) 0.052(3) Uani d . 1 . . O O2 0.5931(3) 0.7572(6) -0.240(3) 0.047(3) Uani d . 1 . . O N1 0.2193(4) 1.0138(7) 0.221(3) 0.034(3) Uani d . 1 . . N N2 0.2819(4) 1.1522(6) -0.061(3) 0.034(3) Uani d . 1 . . N C1 0.3768(5) 0.9011(8) -0.062(4) 0.030(3) Uani d . 1 . . C C2 0.2736(5) 0.9833(8) 0.112(4) 0.032(3) Uani d . 1 . . C C3 0.3085(5) 1.0641(8) -0.049(4) 0.032(3) Uani d . 1 . . C C4 0.4241(5) 0.8373(8) -0.079(4) 0.032(3) Uani d . 1 . . C C5 0.5012(5) 0.6895(8) 0.000(3) 0.027(3) Uani d . 1 . . C C6 0.5327(5) 0.7637(8) -0.150(4) 0.033(3) Uani d . 1 . . C C7 0.5815(6) 0.5801(12) -0.105(6) 0.069(6) Uani d . 1 . . C H7A 0.6031 0.5199 -0.0211 0.083 Uiso calc R 1 . . H H7B 0.5712 0.5679 -0.3376 0.083 Uiso calc R 1 . . H C8 0.6197(5) 0.6668(9) -0.080(4) 0.039(4) Uani d . 1 . . C H8A 0.6590 0.6514 -0.1845 0.047 Uiso calc R 1 . . H H8B 0.6273 0.6818 0.1540 0.047 Uiso calc R 1 . . H 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 0.0326(15) 0.0237(13) 0.064(3) -0.0023(11) 0.010(2) 0.0012(19) S2 0.0299(14) 0.0264(14) 0.052(2) 0.0008(12) 0.0046(18) 0.0042(19) S3 0.0343(15) 0.0261(13) 0.051(2) -0.0009(12) 0.007(2) 0.0079(19) S4 0.0296(14) 0.0257(14) 0.047(2) 0.0016(11) 0.0014(17) 0.0053(16) S5 0.0346(15) 0.0323(14) 0.068(3) 0.0073(13) 0.002(2) -0.004(2) O1 0.047(5) 0.034(4) 0.074(8) 0.008(4) -0.021(7) 0.013(6) O2 0.028(4) 0.041(5) 0.071(8) 0.013(4) -0.001(6) 0.022(6) N1 0.026(4) 0.029(5) 0.046(8) 0.000(4) 0.002(6) -0.003(6) N2 0.021(5) 0.019(4) 0.063(9) 0.007(4) -0.001(6) 0.002(5) C1 0.033(6) 0.019(5) 0.037(8) -0.005(5) 0.015(7) -0.001(6) C2 0.035(6) 0.030(6) 0.031(8) -0.005(5) -0.006(8) -0.011(7) C3 0.024(6) 0.021(6) 0.051(10) 0.002(4) 0.003(7) 0.010(6) C4 0.025(6) 0.027(6) 0.043(9) -0.007(5) 0.006(7) 0.003(7) C5 0.023(5) 0.024(5) 0.035(9) 0.009(4) -0.001(6) 0.002(6) C6 0.031(6) 0.024(6) 0.045(10) 0.006(5) 0.007(7) 0.004(7) C7 0.055(9) 0.082(12) 0.071(14) 0.053(9) -0.008(10) -0.007(12) C8 0.030(6) 0.044(7) 0.045(10) 0.019(6) 0.002(8) -0.003(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 _geom_angle_publ_flag C2 S1 C1 94.1(6) yes C3 S2 C1 95.1(5) yes C5 S3 C4 93.7(5) yes C6 S4 C4 93.6(6) yes N1 S5 N2 98.8(5) yes C5 O1 C7 107.3(11) yes C6 O2 C8 108.6(9) yes C2 N1 S5 106.0(8) yes C3 N2 S5 106.4(8) yes C4 C1 S2 122.9(9) no C4 C1 S1 121.0(9) no S2 C1 S1 116.1(6) yes N1 C2 C3 113.6(10) yes N1 C2 S1 128.6(10) no C3 C2 S1 117.7(9) yes N2 C3 C2 115.2(10) yes N2 C3 S2 128.5(9) no C2 C3 S2 116.2(8) yes C1 C4 S4 120.7(9) no C1 C4 S3 123.7(9) no S4 C4 S3 115.6(6) yes C6 C5 O1 124.8(10) yes C6 C5 S3 118.2(8) yes O1 C5 S3 116.9(8) no C5 C6 O2 124.9(10) yes C5 C6 S4 118.3(8) yes O2 C6 S4 116.7(9) no C8 C7 O1 110.6(12) yes C8 C7 H7A 109.5 no O1 C7 H7A 109.5 no C8 C7 H7B 109.5 no O1 C7 H7B 109.5 no H7A C7 H7B 108.1 no C7 C8 O2 112.3(11) yes C7 C8 H8A 109.1 no O2 C8 H8A 109.1 no C7 C8 H8B 109.1 no O2 C8 H8B 109.1 no H8A C8 H8B 107.9 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 . 1.726(11) yes S1 C1 . 1.796(12) yes S2 C3 . 1.740(12) yes S2 C1 . 1.758(12) yes S3 C5 . 1.751(11) yes S3 C4 . 1.765(12) yes S4 C6 . 1.754(11) yes S4 C4 . 1.759(12) yes S5 N1 . 1.653(9) yes S5 N2 . 1.662(10) yes O1 C5 . 1.369(12) yes O1 C7 . 1.468(19) yes O2 C6 . 1.363(12) yes O2 C8 . 1.453(14) yes N1 C2 . 1.317(14) yes N2 C3 . 1.281(12) yes C1 C4 . 1.322(14) yes C2 C3 . 1.444(16) yes C5 C6 . 1.323(16) yes C7 C8 . 1.400(18) yes C7 H7A . 0.9700 no C7 H7B . 0.9700 no C8 H8A . 0.9700 no C8 H8B . 0.9700 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 S5 3.541(5) 3_544 yes S1 S5 3.547(5) 3_545 yes S2 S4 3.519(5) 2_675 yes S3 S5 3.610(5) 3_544 yes S4 S2 3.519(5) 2_674 yes S5 S1 3.541(5) 3 yes S5 S1 3.547(5) 3_554 yes S5 S3 3.610(5) 3 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 _geom_torsion_publ_flag N2 S5 N1 C2 0.2(12) no N1 S5 N2 C3 -0.1(12) no C3 S2 C1 C4 -171.5(13) no C3 S2 C1 S1 8.5(10) no C2 S1 C1 C4 171.5(12) no C2 S1 C1 S2 -8.4(10) no S5 N1 C2 C3 -0.2(16) no S5 N1 C2 S1 -177.2(11) no C1 S1 C2 N1 -178.2(15) no C1 S1 C2 C3 4.9(13) no S5 N2 C3 C2 0.0(16) no S5 N2 C3 S2 177.0(11) no N1 C2 C3 N2 0(2) no S1 C2 C3 N2 177.5(12) no N1 C2 C3 S2 -177.3(12) no S1 C2 C3 S2 0.1(16) no C1 S2 C3 N2 177.8(15) no C1 S2 C3 C2 -5.2(13) no S2 C1 C4 S4 -1.5(18) no S1 C1 C4 S4 178.5(9) no S2 C1 C4 S3 179.2(9) no S1 C1 C4 S3 -0.7(18) no C6 S4 C4 C1 173.3(12) no C6 S4 C4 S3 -7.4(10) no C5 S3 C4 C1 -173.9(13) no C5 S3 C4 S4 6.8(9) no C7 O1 C5 C6 -18.5(19) no C7 O1 C5 S3 159.1(11) no C4 S3 C5 C6 -3.2(13) no C4 S3 C5 O1 179.0(12) no O1 C5 C6 O2 1(2) no S3 C5 C6 O2 -177.1(11) no O1 C5 C6 S4 176.1(11) no S3 C5 C6 S4 -1.5(17) no C8 O2 C6 C5 -12(2) no C8 O2 C6 S4 172.1(10) no C4 S4 C6 C5 5.4(14) no C4 S4 C6 O2 -178.7(11) no C5 O1 C7 C8 49.7(17) no O1 C7 C8 O2 -66.4(18) no C6 O2 C8 C7 44.5(17) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21131946 2 PubChem 139065841