#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/02/2200211.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_2200211 loop_ _publ_author_name 'Tomura, Masaaki' 'Yamashita, Yoshiro' _publ_section_title ; Tetrathiafulvalene with a fused pyrazine ring ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o307 _journal_page_last o308 _journal_paper_doi 10.1107/S1600536801003701 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C8 H4 N2 S4' _chemical_formula_moiety 'C8 H4 N2 S4' _chemical_formula_sum 'C8 H4 N2 S4' _chemical_formula_weight 256.37 _chemical_melting_point 182 _chemical_name_common ; pyrazinotetrathiafulvalene ; _chemical_name_systematic ; 2-(1,3-dithiol-2-ylidene)-2,3-dihydro-1,3-dithia-4,7-diazaindene ; _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 96.89(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.481(2) _cell_length_b 9.1928(9) _cell_length_c 12.8980(14) _cell_measurement_reflns_used 24 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 42.75 _cell_measurement_theta_min 9.66 _cell_volume 998.3(3) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1992)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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 .996 _diffrn_measured_fraction_theta_max .996 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w _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 .0841 _diffrn_reflns_av_sigmaI/netI .1940 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2060 _diffrn_reflns_theta_full 74.21 _diffrn_reflns_theta_max 74.21 _diffrn_reflns_theta_min 5.93 _diffrn_standards_decay_% 4.9 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 8.393 _exptl_absorpt_correction_T_max .6790 _exptl_absorpt_correction_T_min .1342 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 520 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .05 _exptl_crystal_size_min .05 _refine_diff_density_max .472 _refine_diff_density_min -.620 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 2026 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all .2738 _refine_ls_R_factor_gt .0794 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; calc w = 1/[\s^2^(Fo^2^)+(0.0473P)^2^] where P = (Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1984 _reflns_number_gt 663 _reflns_number_total 2026 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6031.cif _cod_data_source_block I _cod_original_cell_volume 998.4(3) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2200211 _cod_database_fobs_code 2200211 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_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 .6493(3) .1589(3) .0282(2) .0674(10) Uani d . 1 . . S S2 .8472(3) .3437(3) -.0918(2) .0654(10) Uani d . 1 . . S S3 .7875(3) -.1295(3) -.0841(2) .0624(9) Uani d . 1 . . S S4 .9782(4) .0714(3) -.2010(2) .0691(10) Uani d . 1 . . S N1 .9250(10) -.3509(10) -.1734(7) .066(3) Uani d . 1 . . N N2 1.1014(9) -.1626(10) -.2882(6) .057(2) Uani d . 1 . . N C1 .7889(11) .1682(12) -.0620(7) .050(3) Uani d . 1 . . C C2 .6431(15) .3437(12) .0447(9) .079(4) Uani d . 1 . . C H2 .5781 .3828 .0908 .095 Uiso calc R 1 . . H C3 .7305(15) .4331(13) -.0079(10) .082(4) Uani d . 1 . . C H3 .7293 .5337 -.0005 .098 Uiso calc R 1 . . H C4 .8439(11) .0490(13) -.1063(7) .053(3) Uani d . 1 . . C C5 .9170(12) -.2081(13) -.1663(8) .052(3) Uani d . 1 . . C C6 1.0049(12) -.1131(11) -.2221(8) .056(3) Uani d . 1 . . C C7 1.0256(13) -.3999(13) -.2385(9) .070(4) Uani d . 1 . . C H7 1.0386 -.4996 -.2465 .084 Uiso calc R 1 . . H C8 1.1105(13) -.3038(15) -.2941(9) .069(4) Uani d . 1 . . C H8 1.1782 -.3430 -.3384 .083 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 .068(2) .084(2) .0552(19) .0057(18) .0270(16) .0009(17) S2 .069(2) .061(2) .069(2) .0031(17) .0229(18) -.0044(18) S3 .067(2) .0610(19) .066(2) -.0009(16) .0368(16) .0047(16) S4 .072(2) .0667(19) .077(2) -.0049(17) .0468(18) .0043(18) N1 .054(6) .067(7) .076(7) .002(6) .004(5) -.004(6) N2 .049(5) .075(7) .049(6) .012(5) .018(4) -.015(5) C1 .037(6) .079(8) .033(6) -.002(6) .005(5) -.001(6) C2 .102(10) .086(9) .052(8) .048(8) .020(7) -.012(7) C3 .098(11) .067(8) .082(10) .028(8) .021(8) -.011(8) C4 .040(6) .079(8) .040(7) -.003(6) .004(5) -.002(6) C5 .051(7) .064(8) .043(7) .005(6) .014(5) .000(6) C6 .047(7) .065(7) .059(7) .017(6) .015(6) -.010(6) C7 .063(9) .073(8) .079(10) .004(7) .025(7) -.018(7) C8 .051(8) .092(10) .060(8) .022(7) -.010(6) -.026(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .3331 .5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 0 6 0 -4 1 -2 0 -2 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 93.8(6) no C3 S2 C1 95.8(5) no C5 S3 C4 94.8(5) no C6 S4 C4 95.8(5) no C7 N1 C5 114.8(10) no C8 N2 C6 115.1(10) no C4 C1 S2 122.6(7) no C4 C1 S1 122.5(8) no S2 C1 S1 115.0(6) no C3 C2 S1 121.1(9) no C3 C2 H2 119.4 no S1 C2 H2 119.4 no C2 C3 S2 114.3(9) no C2 C3 H3 122.9 no S2 C3 H3 122.9 no C1 C4 S3 125.6(7) no C1 C4 S4 118.7(8) no S3 C4 S4 115.7(6) no N1 C5 C6 123.3(9) no N1 C5 S3 119.3(8) no C6 C5 S3 117.4(8) no N2 C6 C5 121.4(9) no N2 C6 S4 122.4(8) no C5 C6 S4 116.1(8) no N1 C7 C8 121.0(11) no N1 C7 H7 119.5 no C8 C7 H7 119.5 no N2 C8 C7 124.3(11) no N2 C8 H8 117.8 no C7 C8 H8 117.8 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 . 1.714(11) no S1 C1 . 1.760(9) no S2 C3 . 1.756(11) no S2 C1 . 1.744(10) no S3 C5 . 1.769(10) no S3 C4 . 1.743(11) no S4 C6 . 1.737(10) no S4 C4 . 1.779(9) no N1 C7 . 1.345(12) no N1 C5 . 1.318(11) no N2 C8 . 1.304(12) no N2 C6 . 1.330(11) no C1 C4 . 1.345(13) no C2 C3 . 1.343(14) no C2 H2 . .9300 no C3 H3 . .9300 no C5 C6 . 1.402(13) no C7 C8 . 1.391(14) no C7 H7 . .9300 no C8 H8 . .9300 no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21132933 2 PubChem 13867582