#------------------------------------------------------------------------------ #$Date: 2022-09-28 16:08:17 +0100 (Wed, 28 Sep 2022) $ #$Revision: 278247 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/04/2000492.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_2000492 loop_ _publ_author_name 'Beddoes, R. L.' 'Russell, J. R.' 'Garner, C. D.' 'Joule, J. A.' _publ_section_title ; Regioselective pyrazine ring reduction of 4-(quinoxalin-2-yl)-1,3-dithiole-2-thione ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2075 _journal_page_last 2078 _journal_paper_doi 10.1107/S0108270192006115 _journal_volume 48 _journal_year 1992 _chemical_formula_sum 'C19 H16 N2 O2 S3' _chemical_formula_weight '400.53 (major component)' _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_type_scat_source IntTabIV _cell_angle_alpha 101.05(9) _cell_angle_beta 103.38(8) _cell_angle_gamma 70.760(10) _cell_formula_units_Z 2 _cell_length_a 12.073(2) _cell_length_b 13.562(2) _cell_length_c 6.2527(5) _cell_measurement_reflns_used 21 _cell_measurement_temperature 296.0(10) _cell_measurement_theta_max 40 _cell_measurement_theta_min 39 _cell_volume 932.9(4) _diffrn_measurement_device 'Rigaku AFC-5R' _diffrn_measurement_method \w/2\q _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 2917 _diffrn_reflns_theta_max 60 _diffrn_standards_decay_% -1.83 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 4.15 _exptl_absorpt_correction_T_max 1.16 _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_type empirical _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.473 _exptl_crystal_description Tabular _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.020 _refine_diff_density_max 0.31 _refine_diff_density_min -0.24 _refine_ls_goodness_of_fit_obs 2.42 _refine_ls_hydrogen_treatment noref _refine_ls_number_parameters 245 _refine_ls_number_reflns 2177 _refine_ls_R_factor_obs 0.054 _refine_ls_shift/esd_max 0.01 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 4F~o~^2^/[\s^2^(F~o~^2^)]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.066 _reflns_number_observed 2177 _reflns_number_total 2762 _reflns_observed_criterion I>3.0\s(I) _cod_data_source_file mu1006.cif _cod_data_source_block mu1006a _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '4F~o~^2^/[\s^2^(F~o~^2^)]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 4F~o~^2^/[\s^2^(F~o~^2^)]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 932.9(2) _cod_database_code 2000492 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,-y,-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z S1 .28450(10) .01400(10) .0388(2) S2 .26970(10) .11480(10) .5019(2) S3 .46030(10) .12020(10) .3098(2) O1 .4448(3) .3971(3) .0869(5) O2 .3437(3) .4498(2) .3686(5) Br .9987(3) .0793(3) .1661(6) N1 .6676(4) .1731(3) .6320(7) N2 .5340(3) .3497(2) .4306(5) C1 .3347(4) .0795(3) .2711(7) C2 .3687(4) .1776(3) .6669(7) C3 .4568(4) .1808(3) .5790(6) C4 .5537(4) .2309(3) .6971(7) C5 .5216(4) .3458(3) .6567(6) C6 .4408(4) .3990(3) .2781(7) C7 .2407(4) .5022(4) .2163(9) C8 .1791(4) .4285(3) .0673(8) C9 .1609(5) .3491(4) .1502(9) C10 .0976(5) .2854(4) .0180(10) C11 .0526(5) .3001(5) -.2010(10) C12 .0701(5) .3785(6) -.2850(10) C13 .1345(5) .4425(4) -.1528(9) C14 .6484(4) .2936(3) .3775(6) C15 .7140(4) .2049(3) .4848(7) C16 .8263(5) .1474(4) .4368(9) C17 .8727(5) .1780(4) .2880(10) C18 .8095(5) .2678(4) .1883(8) C19 .6987(4) .3255(4) .2354(7) H1 .7128 .1101 .6943 H2 .3602 .2084 .8141 H4 .5625 .2296 .8513 H51 .5740 .3788 .7600 H52 .4418 .3815 .6753 H71 .1857 .5524 .2998 H72 .2658 .5373 .1274 H9 .1926 .3382 .3008 H10 .0846 .2313 .0765 H11 .0095 .2556 -.2947 H12 .0377 .3895 -.4350 H13 .1481 .4960 -.2123 H16 .8713 .0868 .5076 H17 .9486 .1373 .2543 H18 .8423 .2893 .0868 H19 .6563 .3882 .1702 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 S2 C2 97.5(2) C1 S3 C3 97.6(2) C6 O2 C7 114.5(3) C4 N1 C15 123.4(4) C5 N2 C6 122.7(3) C5 N2 C14 115.0(3) C6 N2 C14 122.2(3) S1 C1 S2 124.3(3) S1 C1 S3 123.6(3) S2 C1 S3 112.1(2) S2 C2 C3 117.0(3) S3 C3 C2 115.8(3) S3 C3 C4 119.0(3) C2 C3 C4 125.2(4) N1 C4 C3 111.9(3) N1 C4 C5 108.8(3) C3 C4 C5 112.2(4) N2 C5 C4 109.7(3) O1 C6 O2 124.0(4) O1 C6 N2 124.7(4) O2 C6 N2 111.4(3) O2 C7 C8 113.2(4) N1 C15 C14 120.9(4) N1 C15 C16 120.1(4) N2 C14 C15 117.1(4) N2 C14 C19 123.2(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.650(4) S2 C1 1.714(4) S2 C2 1.726(5) S3 C1 1.730(5) S3 C3 1.729(4) O1 C6 1.203(5) O2 C6 1.340(5) O2 C7 1.445(5) Br C17 1.868(6) N1 C4 1.449(6) N1 C15 1.378(5) N2 C5 1.468(5) N2 C6 1.369(5) N2 C14 1.422(5) C2 C3 1.322(6) C3 C4 1.519(6) C4 C5 1.533(6) C7 C8 1.495(6) C8 C9 1.378(6) C8 C13 1.382(6) C9 C10 1.373(7) C10 C11 1.380(9) C11 C12 1.363(9) C12 C13 1.383(8) C14 C15 1.399(6) C14 C19 1.384(6) C15 C16 1.393(6) C16 C17 1.376(7) C17 C18 1.383(7) C18 C19 1.376(6)