#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2207364.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_2207364 loop_ _publ_author_name 'Pan, Ning-Ning' 'Wang, Wei' 'Zhao, Bing' _publ_section_title ; 2,3-Bis(1-methyl-1H-imidazol-2-ylsulfanylmethyl)quinoxaline ; _journal_coeditor_code TK6275 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3939 _journal_page_last o3940 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C18 H18 N6 S2' _chemical_formula_moiety 'C18 H18 N6 S2' _chemical_formula_sum 'C18 H18 N6 S2' _chemical_formula_weight 382.50 _chemical_melting_point 374 _chemical_name_systematic ; 2,3-Bis(1-methyl-1H-imidazol-2-ylsulfanylmethyl)quinoxaline ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 96.495(4) _cell_angle_beta 97.418(3) _cell_angle_gamma 109.863(3) _cell_formula_units_Z 2 _cell_length_a 6.8978(14) _cell_length_b 9.953(2) _cell_length_c 14.556(3) _cell_measurement_reflns_used 1798 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 26.07 _cell_measurement_theta_min 2.86 _cell_volume 918.7(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_av_sigmaI/netI 0.041 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 4713 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 1.4 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_T_max 0.958 _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.24 _refine_diff_density_min -0.24 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 237 _refine_ls_number_reflns 3244 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.02 _refine_ls_R_factor_all 0.062 _refine_ls_R_factor_gt 0.040 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.067P)^2^+0.146P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.107 _refine_ls_wR_factor_ref 0.122 _reflns_number_gt 2350 _reflns_number_total 3244 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file tk6275.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (4 times). '_geom_angle_publ_flag' value 'Yes' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (4 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2207364 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_type_symbol S1 1.35146(10) 0.12202(7) 0.46720(5) 0.0503(2) Uani d . 1 S S2 0.77718(12) 0.23331(7) 0.27469(5) 0.0572(2) Uani d . 1 S N1 1.1229(3) -0.0871(2) 0.30655(14) 0.0425(5) Uani d . 1 N N2 0.7135(3) -0.1509(2) 0.20914(14) 0.0429(5) Uani d . 1 N N3 1.6020(3) 0.3723(2) 0.58181(14) 0.0464(5) Uani d . 1 N N4 1.2665(3) 0.3184(2) 0.58856(16) 0.0566(6) Uani d . 1 N N5 0.5893(3) 0.1870(2) 0.09107(15) 0.0467(5) Uani d . 1 N N6 0.9146(3) 0.1882(2) 0.11143(18) 0.0586(6) Uani d . 1 N C1 1.0296(4) -0.2055(2) 0.23596(17) 0.0409(6) Uani d . 1 C C2 1.1400(4) -0.2976(3) 0.21369(19) 0.0507(7) Uani d . 1 C H2 1.2760 -0.2766 0.2449 0.061 Uiso calc R 1 H C3 1.0458(5) -0.4172(3) 0.1463(2) 0.0595(8) Uani d . 1 C H3 1.1178 -0.4785 0.1320 0.071 Uiso calc R 1 H C4 0.8436(5) -0.4492(3) 0.0984(2) 0.0614(8) Uani d . 1 C H4 0.7824 -0.5313 0.0523 0.074 Uiso calc R 1 H C5 0.7332(5) -0.3616(3) 0.11812(19) 0.0558(7) Uani d . 1 C H5 0.5981 -0.3838 0.0855 0.067 Uiso calc R 1 H C6 0.8260(4) -0.2377(3) 0.18814(17) 0.0419(6) Uani d . 1 C C7 1.0119(4) -0.0083(2) 0.32687(16) 0.0386(5) Uani d . 1 C C8 0.8033(3) -0.0407(2) 0.27681(16) 0.0375(5) Uani d . 1 C C9 1.1045(4) 0.1174(3) 0.40570(19) 0.0535(7) Uani d . 1 C H9A 1.0078 0.1105 0.4493 0.064 Uiso calc R 1 H H9B 1.1253 0.2068 0.3809 0.064 Uiso calc R 1 H C10 1.4038(4) 0.2785(3) 0.54957(16) 0.0410(6) Uani d . 1 C C11 1.3839(5) 0.4449(3) 0.6483(2) 0.0597(8) Uani d . 1 C H11 1.3291 0.4997 0.6858 0.072 Uiso calc R 1 H C12 1.5877(5) 0.4794(3) 0.64540(19) 0.0572(7) Uani d . 1 C H12 1.6976 0.5599 0.6797 0.069 Uiso calc R 1 H C13 1.7926(4) 0.3652(4) 0.5518(2) 0.0762(10) Uani d . 1 C H13A 1.8091 0.2764 0.5639 0.114 Uiso calc R 1 H H13B 1.9112 0.4459 0.5861 0.114 Uiso calc R 1 H H13C 1.7829 0.3684 0.4858 0.114 Uiso calc R 1 H C14 0.6765(4) 0.0502(3) 0.30156(18) 0.0472(6) Uani d . 1 C H14A 0.6722 0.0564 0.3682 0.057 Uiso calc R 1 H H14B 0.5339 0.0019 0.2677 0.057 Uiso calc R 1 H C15 0.7616(4) 0.1992(2) 0.15380(18) 0.0443(6) Uani d . 1 C C16 0.8366(5) 0.1697(3) 0.0183(2) 0.0657(8) Uani d . 1 C H16 0.9105 0.1596 -0.0295 0.079 Uiso calc R 1 H C17 0.6391(5) 0.1680(3) 0.00393(19) 0.0574(7) Uani d . 1 C H17 0.5538 0.1563 -0.0536 0.069 Uiso calc R 1 H C18 0.3942(4) 0.1972(3) 0.1122(2) 0.0713(9) Uani d . 1 C H18A 0.3528 0.1436 0.1617 0.107 Uiso calc R 1 H H18B 0.2872 0.1576 0.0571 0.107 Uiso calc R 1 H H18C 0.4135 0.2969 0.1318 0.107 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 0.0429(4) 0.0548(4) 0.0532(4) 0.0259(3) -0.0003(3) -0.0073(3) S2 0.0755(5) 0.0471(4) 0.0524(4) 0.0343(4) -0.0027(4) -0.0002(3) N1 0.0395(11) 0.0399(12) 0.0480(12) 0.0158(10) 0.0058(9) 0.0041(10) N2 0.0414(11) 0.0425(12) 0.0429(12) 0.0138(10) 0.0057(9) 0.0060(10) N3 0.0391(12) 0.0513(13) 0.0440(12) 0.0122(10) 0.0043(9) 0.0053(10) N4 0.0461(13) 0.0598(15) 0.0637(15) 0.0228(11) 0.0125(11) -0.0051(12) N5 0.0419(12) 0.0446(12) 0.0548(14) 0.0193(10) 0.0024(10) 0.0088(10) N6 0.0465(13) 0.0588(15) 0.0750(17) 0.0221(11) 0.0165(12) 0.0125(12) C1 0.0467(14) 0.0352(13) 0.0425(14) 0.0149(11) 0.0125(11) 0.0076(11) C2 0.0573(16) 0.0455(15) 0.0556(16) 0.0245(13) 0.0156(13) 0.0084(13) C3 0.078(2) 0.0469(16) 0.0613(18) 0.0285(15) 0.0249(16) 0.0077(14) C4 0.087(2) 0.0358(15) 0.0540(17) 0.0140(15) 0.0154(16) -0.0011(12) C5 0.0606(17) 0.0463(16) 0.0493(16) 0.0092(14) 0.0030(13) 0.0026(13) C6 0.0473(14) 0.0367(13) 0.0398(13) 0.0114(12) 0.0102(11) 0.0079(11) C7 0.0399(13) 0.0368(13) 0.0407(13) 0.0159(11) 0.0072(11) 0.0064(10) C8 0.0378(13) 0.0387(13) 0.0384(13) 0.0143(11) 0.0085(10) 0.0115(11) C9 0.0491(15) 0.0512(16) 0.0590(17) 0.0264(13) -0.0053(13) -0.0058(13) C10 0.0368(13) 0.0458(14) 0.0401(13) 0.0163(12) 0.0051(11) 0.0040(11) C11 0.071(2) 0.0530(18) 0.0574(18) 0.0322(16) 0.0049(15) -0.0064(14) C12 0.0648(19) 0.0414(15) 0.0543(17) 0.0127(14) -0.0021(14) -0.0018(13) C13 0.0392(16) 0.107(3) 0.069(2) 0.0131(17) 0.0132(14) -0.0014(19) C14 0.0451(14) 0.0559(16) 0.0476(15) 0.0266(13) 0.0089(12) 0.0093(12) C15 0.0430(14) 0.0370(14) 0.0555(16) 0.0180(12) 0.0061(12) 0.0097(11) C16 0.073(2) 0.064(2) 0.068(2) 0.0260(17) 0.0308(17) 0.0183(16) C17 0.072(2) 0.0489(16) 0.0469(16) 0.0183(15) 0.0034(14) 0.0103(13) C18 0.0486(17) 0.081(2) 0.088(2) 0.0333(16) 0.0022(16) 0.0066(18) 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 ; 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 C10 S1 C9 96.95(11) ? C15 S2 C14 101.70(11) ? C7 N1 C1 117.0(2) ? C8 N2 C6 117.0(2) ? C10 N3 C12 106.3(2) ? C10 N3 C13 127.1(2) ? C12 N3 C13 126.6(2) ? C10 N4 C11 104.5(2) ? C15 N5 C17 106.2(2) ? C15 N5 C18 127.1(2) ? C17 N5 C18 126.6(2) ? C15 N6 C16 104.4(2) ? N1 C1 C6 120.9(2) ? N1 C1 C2 119.3(2) ? C6 C1 C2 119.7(2) ? C3 C2 C1 119.5(3) ? C3 C2 H2 120.3 ? C1 C2 H2 120.3 ? C2 C3 C4 120.9(3) ? C2 C3 H3 119.5 ? C4 C3 H3 119.5 ? C5 C4 C3 120.9(3) ? C5 C4 H4 119.5 ? C3 C4 H4 119.5 ? C4 C5 C6 119.4(3) ? C4 C5 H5 120.3 ? C6 C5 H5 120.3 ? N2 C6 C1 121.1(2) ? N2 C6 C5 119.4(2) ? C1 C6 C5 119.5(2) ? N1 C7 C8 121.9(2) ? N1 C7 C9 118.6(2) ? C8 C7 C9 119.5(2) ? N2 C8 C7 122.0(2) ? N2 C8 C14 116.6(2) ? C7 C8 C14 121.3(2) ? C7 C9 S1 111.30(17) ? C7 C9 H9A 109.4 ? S1 C9 H9A 109.4 ? C7 C9 H9B 109.4 ? S1 C9 H9B 109.4 ? H9A C9 H9B 108.0 ? S1 C10 N3 121.20(18) yes S1 C10 N4 126.74(19) yes N3 C10 N4 112.0(2) yes C12 C11 N4 111.0(2) ? C12 C11 H11 124.5 ? N4 C11 H11 124.5 ? C11 C12 N3 106.1(2) ? C11 C12 H12 126.9 ? N3 C12 H12 126.9 ? N3 C13 H13A 109.5 ? N3 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? N3 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? C8 C14 S2 114.05(17) ? C8 C14 H14A 108.7 ? S2 C14 H14A 108.7 ? C8 C14 H14B 108.7 ? S2 C14 H14B 108.7 ? H14A C14 H14B 107.6 ? S2 C15 N5 123.13(19) yes S2 C15 N6 125.0(2) yes N5 C15 N6 111.8(2) yes C17 C16 N6 111.6(3) ? C17 C16 H16 124.2 ? N6 C16 H16 124.2 ? C16 C17 N5 106.0(3) ? C16 C17 H17 127.0 ? N5 C17 H17 127.0 ? N5 C18 H18A 109.5 ? N5 C18 H18B 109.5 ? H18A C18 H18B 109.5 ? N5 C18 H18C 109.5 ? H18A C18 H18C 109.5 ? H18B C18 H18C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C9 1.803(3) yes S1 C10 1.754(2) yes S2 C14 1.825(3) yes S2 C15 1.736(3) yes N1 C7 1.305(3) ? N1 C1 1.378(3) ? N2 C8 1.301(3) ? N2 C6 1.378(3) ? N3 C10 1.352(3) ? N3 C12 1.369(3) ? N3 C13 1.459(3) ? N4 C10 1.311(3) ? N4 C11 1.369(3) ? N5 C15 1.362(3) ? N5 C17 1.365(3) ? N5 C18 1.452(3) ? N6 C15 1.319(3) ? N6 C16 1.360(4) ? C1 C6 1.396(3) ? C1 C2 1.413(3) ? C2 C3 1.359(4) ? C2 H2 0.9300 ? C3 C4 1.389(4) ? C3 H3 0.9300 ? C4 C5 1.369(4) ? C4 H4 0.9300 ? C5 C6 1.408(3) ? C5 H5 0.9300 ? C7 C8 1.437(3) ? C7 C9 1.494(3) ? C8 C14 1.503(3) ? C9 H9A 0.9700 ? C9 H9B 0.9700 ? C11 C12 1.336(4) ? C11 H11 0.9300 ? C12 H12 0.9300 ? C13 H13A 0.9600 ? C13 H13B 0.9600 ? C13 H13C 0.9600 ? C14 H14A 0.9700 ? C14 H14B 0.9700 ? C16 C17 1.345(4) ? C16 H16 0.9300 ? C17 H17 0.9300 ? C18 H18A 0.9600 ? C18 H18B 0.9600 ? C18 H18C 0.9600 ? 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 C7 N1 C1 C6 0.7(3) C7 N1 C1 C2 -177.6(2) N1 C1 C2 C3 177.8(2) C6 C1 C2 C3 -0.5(4) C1 C2 C3 C4 0.7(4) C2 C3 C4 C5 -0.4(4) C3 C4 C5 C6 -0.2(4) C8 N2 C6 C1 -1.7(3) C8 N2 C6 C5 177.5(2) N1 C1 C6 N2 0.9(4) C2 C1 C6 N2 179.2(2) N1 C1 C6 C5 -178.3(2) C2 C1 C6 C5 0.0(4) C4 C5 C6 N2 -178.9(2) C4 C5 C6 C1 0.4(4) C1 N1 C7 C8 -1.4(3) C1 N1 C7 C9 177.5(2) C6 N2 C8 C7 1.0(3) C6 N2 C8 C14 -177.9(2) N1 C7 C8 N2 0.6(4) C9 C7 C8 N2 -178.3(2) N1 C7 C8 C14 179.4(2) C9 C7 C8 C14 0.5(3) N1 C7 C9 S1 -6.5(3) C8 C7 C9 S1 172.42(18) C10 S1 C9 C7 179.8(2) C11 N4 C10 N3 0.5(3) C11 N4 C10 S1 179.0(2) C12 N3 C10 N4 -0.4(3) C13 N3 C10 N4 -177.7(3) C12 N3 C10 S1 -178.94(18) C13 N3 C10 S1 3.8(4) C9 S1 C10 N4 35.5(3) C9 S1 C10 N3 -146.2(2) C10 N4 C11 C12 -0.4(3) N4 C11 C12 N3 0.2(3) C10 N3 C12 C11 0.1(3) C13 N3 C12 C11 177.4(3) N2 C8 C14 S2 -113.0(2) C7 C8 C14 S2 68.1(3) C15 S2 C14 C8 61.0(2) C16 N6 C15 N5 0.6(3) C16 N6 C15 S2 -176.7(2) C17 N5 C15 N6 -0.4(3) C18 N5 C15 N6 -178.4(2) C17 N5 C15 S2 176.96(18) C18 N5 C15 S2 -1.1(4) C14 S2 C15 N6 -92.9(2) C14 S2 C15 N5 90.1(2) C15 N6 C16 C17 -0.6(3) N6 C16 C17 N5 0.4(3) C15 N5 C17 C16 0.0(3) C18 N5 C17 C16 178.1(3)