#------------------------------------------------------------------------------ #$Date: 2018-12-19 05:20:10 +0200 (Wed, 19 Dec 2018) $ #$Revision: 212657 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/27/2242796.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_2242796 loop_ _publ_author_name 'Popek, Rafal' 'Crundwell, Guy' _publ_section_title ; Crystal structures of 2,3-bis(thiophen-2-yl)pyrido[2,3-b]pyrazine and 7-bromo-2,3-bis(thiophen-2-yl)pyrido[2,3-b]pyrazine ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first 89 _journal_page_last 93 _journal_paper_doi 10.1107/S2056989018016882 _journal_volume 75 _journal_year 2019 _chemical_formula_iupac 'C15 H8 Br N3 S2' _chemical_formula_moiety 'C15 H8 Br N3 S2' _chemical_formula_sum 'C15 H8 Br N3 S2' _chemical_formula_weight 374.27 _chemical_melting_point 445 _chemical_name_common ; 7-bromo-2,3-bis(thien-2-yl)pyrido[2,3-b]pyrazine ; _chemical_name_systematic ; 7-Bromo-2,3-bis(thiophen-2-yl)pyrido[2,3-b]pyrazine ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 95.466(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.8336(2) _cell_length_b 29.4731(10) _cell_length_c 8.3160(3) _cell_measurement_reflns_used 9441 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 32.2030 _cell_measurement_theta_min 4.4790 _cell_volume 1423.30(9) _computing_cell_refinement ; CrysAlis PRO (Rigaku OD, 2018) ; _computing_data_collection ; CrysAlis PRO (Rigaku OD, 2018) ; _computing_data_reduction ; CrysAlis PRO (Rigaku OD, 2018) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008) ; _computing_publication_material ; OLEX2 (Dolomanov et al., 2009) ; _computing_structure_refinement ; SHELXL97 (Sheldrick, 2008) ; _computing_structure_solution ; SHELXS97 (Sheldrick, 2008) ; _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.1790 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.912 _diffrn_measurement_device_type 'Rigaku Xcalibur Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_unetI/netI 0.0232 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 34519 _diffrn_reflns_theta_full 29.00 _diffrn_reflns_theta_max 33.91 _diffrn_reflns_theta_min 4.24 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 3.176 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.45534 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Rigaku OD, 2018) ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.630 _refine_diff_density_min -0.672 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 5255 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.079 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0425 _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^)+(0.0474P)^2^+0.9400P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1026 _refine_ls_wR_factor_ref 0.1100 _reflns_number_gt 4166 _reflns_number_total 5255 _reflns_threshold_expression >2sigma(I) _cod_data_source_file xi2011sup1.cif _cod_data_source_block 2 _cod_database_code 2242796 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -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_occupancy Br Br1 0.69446(4) 0.018840(9) 0.30276(3) 0.04319(9) Uani d 1 S S2 0.62946(10) -0.11087(2) -0.49251(7) 0.04132(14) Uani d 1 S S1 1.54351(12) -0.19256(2) -0.09942(10) 0.05248(18) Uani d 1 N N3 0.8311(3) -0.08963(6) -0.1758(2) 0.0312(3) Uani d 1 C C12 0.8921(3) -0.13124(7) -0.4089(3) 0.0294(4) Uani d 1 C C7 0.9600(3) -0.12031(7) -0.2402(2) 0.0290(4) Uani d 1 C C2 1.1218(4) -0.08478(7) 0.0484(3) 0.0314(4) Uani d 1 C C6 0.9043(3) -0.07298(7) -0.0283(2) 0.0290(4) Uani d 1 C C13 1.0082(4) -0.15121(8) -0.5255(3) 0.0354(4) Uani d 1 H H13 1.1549 -0.1635 -0.5056 0.042 Uiso calc 1 N N1 1.2404(3) -0.11997(7) -0.0083(2) 0.0342(4) Uani d 1 N N2 1.2152(4) -0.06423(8) 0.1847(3) 0.0428(5) Uani d 1 C C1 1.1566(4) -0.13963(7) -0.1436(3) 0.0298(4) Uani d 1 C C5 0.7682(4) -0.04198(8) 0.0495(3) 0.0327(4) Uani d 1 H H5 0.6198 -0.0346 0.0066 0.039 Uiso calc 1 C C4 0.8620(4) -0.02319(7) 0.1898(3) 0.0330(4) Uani d 1 C C8 1.2653(4) -0.18271(7) -0.1791(3) 0.0331(4) Uani d 1 C C14 0.8825(4) -0.15116(8) -0.6789(3) 0.0386(5) Uani d 1 H H14 0.9366 -0.1637 -0.7707 0.046 Uiso calc 1 C C15 0.6754(4) -0.13092(8) -0.6780(3) 0.0395(5) Uani d 1 H H15 0.5699 -0.1283 -0.7686 0.047 Uiso calc 1 C C3 1.0885(4) -0.03388(9) 0.2503(3) 0.0413(5) Uani d 1 H H3 1.1521 -0.0186 0.3419 0.050 Uiso calc 1 C C9 1.1615(5) -0.22302(8) -0.2534(3) 0.0445(6) Uani d 1 H H9 1.0113 -0.2255 -0.3013 0.053 Uiso calc 1 C C10 1.3303(6) -0.25845(9) -0.2402(4) 0.0575(8) Uani d 1 H H10 1.3004 -0.2874 -0.2817 0.069 Uiso calc 1 C C11 1.5344(6) -0.24684(10) -0.1638(4) 0.0589(8) Uani d 1 H H11 1.6584 -0.2667 -0.1479 0.071 Uiso calc 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 Br1 0.04705(15) 0.04449(14) 0.03805(13) 0.00908(10) 0.00417(10) -0.01197(10) S2 0.0361(3) 0.0475(3) 0.0388(3) 0.0120(2) -0.0047(2) -0.0046(2) S1 0.0458(3) 0.0422(3) 0.0694(5) 0.0123(3) 0.0051(3) 0.0048(3) N3 0.0301(8) 0.0319(9) 0.0308(8) 0.0037(7) -0.0023(6) -0.0041(7) C12 0.0274(9) 0.0279(9) 0.0320(9) 0.0004(7) -0.0016(7) -0.0012(7) C7 0.0294(9) 0.0272(9) 0.0301(9) 0.0005(7) 0.0007(7) -0.0005(7) C2 0.0304(9) 0.0329(10) 0.0299(9) 0.0045(8) -0.0019(7) -0.0015(8) C6 0.0291(9) 0.0282(9) 0.0291(9) 0.0034(7) -0.0003(7) -0.0006(7) C13 0.0326(10) 0.0393(11) 0.0337(10) 0.0016(9) 0.0010(8) -0.0031(9) N1 0.0333(9) 0.0353(9) 0.0327(9) 0.0084(7) -0.0031(7) -0.0012(7) N2 0.0382(10) 0.0502(12) 0.0376(10) 0.0112(9) -0.0093(8) -0.0104(9) C1 0.0306(9) 0.0267(9) 0.0323(10) 0.0038(7) 0.0037(7) 0.0003(7) C5 0.0306(9) 0.0343(10) 0.0323(10) 0.0057(8) -0.0012(8) -0.0021(8) C4 0.0370(10) 0.0316(10) 0.0306(10) 0.0021(8) 0.0041(8) -0.0027(8) C8 0.0367(10) 0.0285(9) 0.0345(10) 0.0057(8) 0.0058(8) 0.0030(8) C14 0.0479(13) 0.0365(11) 0.0313(10) -0.0003(9) 0.0031(9) -0.0030(8) C15 0.0481(13) 0.0368(11) 0.0314(11) 0.0015(10) -0.0085(9) -0.0011(8) C3 0.0432(12) 0.0451(13) 0.0334(11) 0.0070(10) -0.0076(9) -0.0106(9) C9 0.0523(14) 0.0343(12) 0.0476(13) 0.0153(10) 0.0085(11) 0.0000(10) C10 0.075(2) 0.0290(12) 0.072(2) 0.0045(12) 0.0257(16) -0.0035(12) C11 0.0594(18) 0.0402(14) 0.080(2) 0.0221(13) 0.0240(16) 0.0075(14) 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' Br Br -0.2901 2.4595 '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 C15 S2 C12 91.95(11) no C11 S1 C8 92.17(14) no C7 N3 C6 118.26(18) no C7 C12 S2 117.37(15) no C13 C12 S2 110.13(16) no C13 C12 C7 132.08(19) no N3 C7 C12 115.37(18) no N3 C7 C1 119.60(18) no C1 C7 C12 125.02(18) no N1 C2 C6 119.96(19) no N2 C2 C6 122.8(2) no N2 C2 N1 117.08(19) no N3 C6 C2 120.93(19) no N3 C6 C5 120.64(18) no C5 C6 C2 118.38(19) no C12 C13 H13 123.5 no C12 C13 C14 113.0(2) no C14 C13 H13 123.5 no C1 N1 C2 118.22(18) no C3 N2 C2 117.1(2) no C7 C1 C8 124.32(19) no N1 C1 C7 120.60(18) no N1 C1 C8 114.94(19) no C6 C5 H5 121.3 no C4 C5 C6 117.4(2) no C4 C5 H5 121.3 no C5 C4 Br1 120.71(17) no C5 C4 C3 120.3(2) no C3 C4 Br1 118.93(17) no C1 C8 S1 118.76(17) no C9 C8 S1 111.58(17) no C9 C8 C1 128.9(2) no C13 C14 H14 123.7 no C15 C14 C13 112.6(2) no C15 C14 H14 123.7 no S2 C15 H15 123.9 no C14 C15 S2 112.24(17) no C14 C15 H15 123.9 no N2 C3 C4 123.5(2) no N2 C3 H3 118.3 no C4 C3 H3 118.3 no C8 C9 H9 126.0 no C10 C9 C8 108.0(3) no C10 C9 H9 126.0 no C9 C10 H10 122.5 no C11 C10 C9 115.1(3) no C11 C10 H10 122.5 no S1 C11 H11 123.4 no C10 C11 S1 113.1(2) no C10 C11 H11 123.4 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br1 C4 1.884(2) no S2 C12 1.729(2) no S2 C15 1.697(2) no S1 C8 1.718(2) no S1 C11 1.686(3) no N3 C7 1.321(3) no N3 C6 1.352(3) no C12 C7 1.457(3) no C12 C13 1.368(3) no C7 C1 1.452(3) no C2 C6 1.408(3) no C2 N1 1.356(3) no C2 N2 1.353(3) no C6 C5 1.408(3) no C13 H13 0.9300 no C13 C14 1.410(3) no N1 C1 1.318(3) no N2 C3 1.312(3) no C1 C8 1.462(3) no C5 H5 0.9300 no C5 C4 1.358(3) no C4 C3 1.404(3) no C8 C9 1.446(4) no C14 H14 0.9300 no C14 C15 1.348(3) no C15 H15 0.9300 no C3 H3 0.9300 no C9 H9 0.9300 no C9 C10 1.432(4) no C10 H10 0.9300 no C10 C11 1.339(5) no C11 H11 0.9300 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C3 H3 Br1 3_756 0.93 3.005 3.8360(10) 150 C5 H5 Br1 3_655 0.93 3.049 3.8510(10) 145 C15 H15 N1 1_454 0.93 2.645 3.5720(10) 175 C11 H11 C14 4_656 0.93 2.775 3.6370(10) 155 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 Br1 C4 C3 N2 176.7(2) no S2 C12 C7 N3 -10.8(3) no S2 C12 C7 C1 170.70(17) no S2 C12 C13 C14 -1.8(3) no S1 C8 C9 C10 -1.7(3) no N3 C7 C1 N1 -16.0(3) no N3 C7 C1 C8 159.4(2) no N3 C6 C5 C4 -173.5(2) no C12 S2 C15 C14 -1.6(2) no C12 C7 C1 N1 162.4(2) no C12 C7 C1 C8 -22.2(3) no C12 C13 C14 C15 0.7(3) no C7 N3 C6 C2 5.8(3) no C7 N3 C6 C5 -176.7(2) no C7 C12 C13 C14 -174.0(2) no C7 C1 C8 S1 158.88(17) no C7 C1 C8 C9 -32.0(4) no C2 C6 C5 C4 4.0(3) no C2 N1 C1 C7 8.1(3) no C2 N1 C1 C8 -167.7(2) no C2 N2 C3 C4 2.3(4) no C6 N3 C7 C12 -170.23(19) no C6 N3 C7 C1 8.4(3) no C6 C2 N1 C1 6.1(3) no C6 C2 N2 C3 3.8(4) no C6 C5 C4 Br1 179.77(16) no C6 C5 C4 C3 1.6(3) no C13 C12 C7 N3 161.0(2) no C13 C12 C7 C1 -17.6(4) no C13 C14 C15 S2 0.8(3) no N1 C2 C6 N3 -13.7(3) no N1 C2 C6 C5 168.7(2) no N1 C2 N2 C3 -172.1(2) no N1 C1 C8 S1 -25.5(3) no N1 C1 C8 C9 143.6(2) no N2 C2 C6 N3 170.5(2) no N2 C2 C6 C5 -7.0(4) no N2 C2 N1 C1 -177.9(2) no C1 C8 C9 C10 -171.4(2) no C5 C4 C3 N2 -5.1(4) no C8 S1 C11 C10 -1.2(3) no C8 C9 C10 C11 0.9(4) no C15 S2 C12 C7 175.40(18) no C15 S2 C12 C13 1.91(19) no C9 C10 C11 S1 0.3(4) no C11 S1 C8 C1 172.6(2) no C11 S1 C8 C9 1.7(2) no _cod_database_fobs_code 2242796