#------------------------------------------------------------------------------ #$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/02/2200253.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_2200253 loop_ _publ_author_name 'He Liu' 'Miao Du' 'Ya-Mei Guo' 'Xian-He Bu' _publ_section_title ; 2,3-Bis(2-pyridinio)-5,8-dimethoxyquinoxaline dinitrate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o372 _journal_page_last o374 _journal_paper_doi 10.1107/S1600536801004834 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C20 H18 N4 O2 2+, 2N O3 1-' _chemical_formula_moiety 'C20 H18 N4 O2 2+, 2N O3 1-' _chemical_formula_sum 'C20 H18 N6 O8' _chemical_formula_weight 470.40 _chemical_name_systematic ; 2,3-bis(2-pyridinio)-5,8-dimethoxyquinoxaline dinitrate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90.00 _cell_angle_beta 104.344(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 16.1380(13) _cell_length_b 7.2682(6) _cell_length_c 18.0257(15) _cell_measurement_reflns_used 7963 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 1.3 _cell_volume 2048.4(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'XP (Bruker, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_measurement_device 'Bruker SMART 1000' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .040 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 8042 _diffrn_reflns_theta_max 25.0 _diffrn_standards_decay_% <1 _diffrn_standards_interval_count none _diffrn_standards_number none _exptl_absorpt_coefficient_mu .121 _exptl_absorpt_correction_T_max .982 _exptl_absorpt_correction_T_min .965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '[SAINT (Bruker, 1998) and SADABS (Sheldrick, 1997)]' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 976 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .15 _refine_diff_density_max .29 _refine_diff_density_min -.17 _refine_ls_extinction_coef .0151(12) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref .97 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 309 _refine_ls_number_reflns 3569 _refine_ls_R_factor_gt .042 _refine_ls_shift/su_max .010 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0555P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .110 _reflns_number_gt 2323 _reflns_number_total 3569 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ya6015.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2200253 _cod_database_fobs_code 2200253 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 N1 .40571(10) .6735(2) 1.05675(9) .0341(4) Uani d . 1 . . N N2 .34234(10) .7641(2) .90253(9) .0341(4) Uani d . 1 . . N N3 .14904(10) .8475(2) .94308(9) .0382(4) Uani d . 1 . . N H3A .1714 .8905 .9880 .046 Uiso calc R 1 . . H N4 .20014(10) .5057(2) 1.05107(9) .0388(4) Uani d . 1 . . N H4B .1867 .4736 1.0037 .047 Uiso calc R 1 . . H O1 .57194(9) .7010(2) 1.12419(8) .0511(4) Uani d . 1 . . O O2 .45021(9) .8501(2) .81438(8) .0480(4) Uani d . 1 . . O C2 .32338(12) .6700(3) 1.02416(11) .0314(5) Uani d . 1 . . C C3 .29038(12) .7244(3) .94658(11) .0319(5) Uani d . 1 . . C C4 .42792(12) .7621(3) .93427(11) .0333(5) Uani d . 1 . . C C5 .48624(13) .8119(3) .88965(12) .0376(5) Uani d . 1 . . C C6 .57093(13) .8219(3) .92497(13) .0419(5) Uani d . 1 . . C H6A .6094 .8540 .8963 .050 Uiso calc R 1 . . H C7 .60206(14) .7849(3) 1.00354(13) .0415(5) Uani d . 1 . . C H7A .6605 .7940 1.0256 .050 Uiso calc R 1 . . H C8 .54861(13) .7362(3) 1.04808(12) .0372(5) Uani d . 1 . . C C9 .45968(12) .7223(3) 1.01330(11) .0336(5) Uani d . 1 . . C C10 .50296(15) .9484(4) .77466(13) .0620(7) Uani d . 1 . . C H10A .4719 .9683 .7225 .093 Uiso calc R 1 . . H H10B .5535 .8779 .7756 .093 Uiso calc R 1 . . H H10C .5189 1.0648 .7992 .093 Uiso calc R 1 . . H C11 .65922(14) .7295(4) 1.16291(14) .0606(7) Uani d . 1 . . C H11A .6675 .6999 1.2162 .091 Uiso calc R 1 . . H H11B .6741 .8560 1.1579 .091 Uiso calc R 1 . . H H11C .6949 .6519 1.1408 .091 Uiso calc R 1 . . H C12 .19879(12) .7488(3) .90748(11) .0331(5) Uani d . 1 . . C C13 .16333(13) .6831(3) .83523(12) .0387(5) Uani d . 1 . . C H13A .1963 .6156 .8094 .046 Uiso calc R 1 . . H C14 .07809(14) .7180(3) .80111(13) .0458(6) Uani d . 1 . . C H14A .0538 .6747 .7520 .055 Uiso calc R 1 . . H C15 .02945(14) .8159(3) .83947(13) .0471(6) Uani d . 1 . . C H15A -.0281 .8379 .8171 .057 Uiso calc R 1 . . H C16 .06666(13) .8808(3) .91116(13) .0452(6) Uani d . 1 . . C H16A .0344 .9483 .9377 .054 Uiso calc R 1 . . H C17 .29371(13) .6529(3) 1.15385(11) .0400(5) Uani d . 1 . . C H17A .3425 .7228 1.1733 .048 Uiso calc R 1 . . H C18 .27060(12) .6083(3) 1.07707(11) .0333(5) Uani d . 1 . . C C19 .15032(14) .4520(3) 1.09596(13) .0502(6) Uani d . 1 . . C H19A .1012 .3839 1.0754 .060 Uiso calc R 1 . . H C20 .17103(16) .4962(4) 1.17200(14) .0552(7) Uani d . 1 . . C H20A .1358 .4607 1.2032 .066 Uiso calc R 1 . . H C21 .24455(15) .5939(3) 1.20173(13) .0482(6) Uani d . 1 . . C H21A .2611 .6200 1.2538 .058 Uiso calc R 1 . . H O3 .18556(10) .3121(2) .92612(9) .0576(5) Uani d . 1 . . O O4 .05221(13) .3601(3) .90596(16) .1056(8) Uani d . 1 . . O O5 .10246(15) .2249(3) .82050(12) .1011(8) Uani d . 1 . . O O6 .21296(16) .0560(3) .18721(11) .1036(8) Uani d . 1 . . O O7 .23531(11) .0266(3) .07477(11) .0673(5) Uani d . 1 . . O O8 .11559(12) -.0417(4) .09471(13) .0958(8) Uani d . 1 . . O N5 .11136(15) .2981(3) .88328(13) .0589(6) Uani d . 1 . . N N6 .18783(14) .0156(3) .12064(12) .0516(5) Uani d . 1 . . N 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 N1 .0274(9) .0386(10) .0354(9) -.0006(8) .0062(8) -.0035(8) N2 .0309(10) .0378(10) .0333(9) -.0014(8) .0073(8) -.0013(8) N3 .0333(10) .0463(11) .0332(9) -.0001(8) .0046(8) -.0015(8) N4 .0374(10) .0464(11) .0329(9) -.0073(9) .0092(8) .0011(8) O1 .0294(8) .0810(12) .0377(9) -.0023(8) -.0013(7) .0024(8) O2 .0407(9) .0675(11) .0374(8) -.0109(8) .0126(7) .0034(8) C2 .0294(11) .0354(12) .0287(10) .0001(9) .0059(9) -.0028(9) C3 .0293(11) .0360(12) .0307(11) -.0025(9) .0080(9) -.0023(9) C4 .0298(12) .0334(11) .0370(12) -.0003(9) .0092(9) -.0049(9) C5 .0355(12) .0414(13) .0378(12) -.0012(10) .0125(10) -.0026(10) C6 .0336(12) .0475(14) .0484(13) -.0038(10) .0172(10) -.0065(11) C7 .0284(11) .0424(13) .0538(14) -.0011(10) .0102(10) -.0072(11) C8 .0304(11) .0408(12) .0373(12) .0017(9) .0025(10) -.0061(10) C9 .0303(11) .0329(11) .0381(12) .0007(9) .0093(9) -.0062(9) C10 .0596(16) .084(2) .0489(15) -.0214(15) .0247(12) .0022(14) C11 .0324(13) .094(2) .0495(15) .0041(13) -.0017(11) -.0032(14) C12 .0302(11) .0377(11) .0318(11) -.0024(9) .0082(9) .0032(9) C13 .0365(12) .0433(12) .0350(12) -.0008(10) .0065(10) .0010(10) C14 .0419(13) .0505(14) .0392(13) -.0052(11) -.0012(11) .0023(11) C15 .0300(12) .0531(15) .0532(15) -.0001(11) .0008(11) .0091(12) C16 .0303(12) .0520(14) .0526(14) .0060(11) .0091(11) .0047(12) C17 .0387(12) .0437(13) .0356(12) .0010(10) .0054(10) -.0006(10) C18 .0297(11) .0367(12) .0326(11) .0019(9) .0061(9) .0016(9) C19 .0480(14) .0522(15) .0543(15) -.0114(12) .0202(12) .0033(12) C20 .0674(17) .0565(16) .0528(15) -.0054(14) .0357(13) .0046(13) C21 .0594(15) .0511(14) .0379(13) .0073(13) .0191(12) .0057(11) O3 .0447(10) .0757(12) .0440(9) .0042(9) -.0050(8) -.0106(8) O4 .0436(12) .115(2) .157(2) -.0016(13) .0230(14) .0125(17) O5 .133(2) .1011(18) .0487(12) -.0421(14) -.0172(12) -.0112(11) O6 .173(2) .0816(16) .0438(12) -.0015(15) .0028(13) -.0161(11) O7 .0625(12) .0721(13) .0735(13) -.0099(10) .0283(10) -.0007(10) O8 .0469(12) .131(2) .1087(17) -.0034(13) .0181(12) -.0244(15) N5 .0544(14) .0546(14) .0586(14) -.0148(11) -.0034(13) .0114(11) N6 .0578(14) .0458(12) .0494(13) .0084(10) .0099(11) -.0019(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 '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 .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 '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 N1 C9 118.07(17) yes C3 N2 C4 118.35(17) yes C16 N3 C12 122.51(19) yes C19 N4 C18 122.47(18) yes C8 O1 C11 117.52(18) yes C5 O2 C10 116.03(16) yes N1 C2 C3 121.67(18) no N1 C2 C18 113.16(17) no C3 C2 C18 125.16(17) no N2 C3 C2 120.81(18) no N2 C3 C12 113.23(17) no C2 C3 C12 125.93(17) no N2 C4 C9 120.14(18) no N2 C4 C5 120.23(18) no C9 C4 C5 119.50(18) no C6 C5 O2 125.84(19) no C6 C5 C4 118.5(2) no O2 C5 C4 115.68(18) no C5 C6 C7 121.9(2) no C8 C7 C6 121.5(2) no O1 C8 C7 126.04(19) no O1 C8 C9 115.52(18) no C7 C8 C9 118.43(19) no N1 C9 C4 120.63(18) no N1 C9 C8 119.16(18) no C4 C9 C8 120.20(18) no N3 C12 C13 118.58(18) no N3 C12 C3 118.53(18) no C13 C12 C3 122.82(18) no C12 C13 C14 119.5(2) no C15 C14 C13 120.2(2) no C16 C15 C14 119.0(2) no N3 C16 C15 120.2(2) no C21 C17 C18 120.1(2) no N4 C18 C17 118.38(18) no N4 C18 C2 120.69(17) no C17 C18 C2 120.93(18) no N4 C19 C20 120.4(2) no C19 C20 C21 119.1(2) no C20 C21 C17 119.5(2) no O4 N5 O5 123.3(3) no O4 N5 O3 118.1(2) no O5 N5 O3 118.5(3) no O6 N6 O8 121.4(3) no O6 N6 O7 121.9(2) no O8 N6 O7 116.7(2) 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 N1 C2 . 1.313(2) yes N1 C9 . 1.355(2) yes N2 C3 . 1.322(2) yes N2 C4 . 1.358(2) yes N3 C12 . 1.351(3) yes N3 C16 . 1.333(2) yes N4 C18 . 1.343(2) yes N4 C19 . 1.333(3) yes O1 C8 . 1.354(2) no O1 C11 . 1.424(2) yes O2 C5 . 1.366(2) no O2 C10 . 1.432(3) yes C2 C3 . 1.423(3) no C2 C18 . 1.496(3) no C3 C12 . 1.482(3) no C4 C9 . 1.419(3) no C4 C5 . 1.428(3) no C5 C6 . 1.359(3) no C6 C7 . 1.406(3) no C7 C8 . 1.363(3) no C8 C9 . 1.420(3) no C12 C13 . 1.372(3) no C13 C14 . 1.384(3) no C14 C15 . 1.367(3) no C15 C16 . 1.367(3) no C17 C21 . 1.377(3) no C17 C18 . 1.380(3) no C19 C20 . 1.366(3) no C20 C21 . 1.372(3) no O3 N5 . 1.258(2) no O4 N5 . 1.214(3) no O5 N5 . 1.227(3) no O6 N6 . 1.204(2) no O7 N6 . 1.261(2) no O8 N6 . 1.217(3) 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 _geom_hbond_publ_flag N3 H3a O7 1_566 .860 1.920 2.762(4) 165.81 yes N4 H4b O3 . .860 1.822 2.617(2) 152.77 yes