#------------------------------------------------------------------------------ #$Date: 2015-01-23 12:30:19 +0000 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/22/2012257.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_2012257 loop_ _publ_author_name 'Alfonso, Montserrat' 'Wang, Yi' 'Stoeckli-Evans, Helen' _publ_section_title ; Hydrogen bonding in the inner-salt zwitterion and in two different charged forms of 5,6-bis(2-pyridyl)pyrazine-2,3-dicarboxylic acid ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1184 _journal_page_last 1188 _journal_paper_doi 10.1107/S0108270101010757 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C16 H11 N4 O4 + , P F6 - , 3H2 O' _chemical_formula_sum 'C16 H17 F6 N4 O7 P' _chemical_formula_weight 522.31 _chemical_name_systematic ; 6-carboxy-5-carboxylatopyrazine-2,3-diyldi-2-pyridinium hexafluorophosphate trihydrate ; _space_group_IT_number 13 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yc' _symmetry_space_group_name_H-M 'P 1 2/c 1' _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 106.400(11) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 6.1910(6) _cell_length_b 15.6564(11) _cell_length_c 10.8349(10) _cell_measurement_reflns_used 5000 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.05 _cell_measurement_theta_min 1.65 _cell_volume 1007.48(16) _computing_cell_refinement 'CELL (Stoe & Cie, 2000)' _computing_data_collection 'EXPOSE (Stoe & Cie, 2000)' _computing_data_reduction 'INTEGRATE (Stoe & Cie, 2000)' _computing_molecular_graphics 'PLATON99 (Spek, 1990)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 0.81\%A _diffrn_measured_fraction_theta_full .987 _diffrn_measured_fraction_theta_max .987 _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method '\f oscillation' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .029 _diffrn_reflns_av_sigmaI/netI .019 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 7713 _diffrn_reflns_theta_full 25.87 _diffrn_reflns_theta_max 25.87 _diffrn_reflns_theta_min 3.26 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .242 _exptl_absorpt_correction_type none _exptl_crystal_colour pale_yellow _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 532 _exptl_crystal_size_max .70 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .15 _refine_diff_density_max .25 _refine_diff_density_min -.83 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.197 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 1944 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.197 _refine_ls_R_factor_all .050 _refine_ls_R_factor_gt .044 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1018P)^2^+0.1313P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .152 _reflns_number_gt 1628 _reflns_number_total 1944 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1159.cif _[local]_cod_data_source_block IIIb _[local]_cod_cif_authors_sg_H-M 'P 2/c' _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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 1007.48(15) _cod_database_code 2012257 _cod_database_fobs_code 2012257 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, 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 .4040(3) .09425(10) .34843(16) .0286(4) Uani d . 1 . . N N2 .3208(3) .24229(11) .46196(15) .0302(4) Uani d . 1 . . N H2N .214(6) .2008(19) .451(3) .049(7) Uiso d . 1 . . H O1 .1776(3) -.03754(11) .39442(18) .0473(5) Uani d . 1 . . O O2 .3656(3) -.13016(10) .31136(18) .0478(5) Uani d . 1 . . O H2O .5000 -.124(4) .2500 .101(19) Uiso d S 1 . . H C1 .4356(3) .02054(13) .29450(18) .0293(4) Uani d . 1 . . C C2 .4658(3) .16771(12) .30675(17) .0263(4) Uani d . 1 . . C C3 .4688(3) .24235(13) .39136(17) .0265(4) Uani d . 1 . . C C4 .6261(4) .30703(14) .40890(19) .0334(5) Uani d . 1 . . C H4 .747(5) .3146(17) .359(3) .045(7) Uiso d . 1 . . H C5 .6266(4) .37137(15) .4977(2) .0407(5) Uani d . 1 . . C H5 .725(5) .4157(19) .508(3) .048(8) Uiso d . 1 . . H C6 .4718(4) .36946(15) .5673(2) .0411(6) Uani d . 1 . . C H6 .474(5) .413(2) .634(3) .053(8) Uiso d . 1 . . H C7 .3190(4) .30384(14) .54757(19) .0363(5) Uani d . 1 . . C H7 .215(5) .2940(17) .592(3) .042(7) Uiso d . 1 . . H C8 .3177(4) -.05412(14) .3380(2) .0361(5) Uani d . 1 . . C O1W -.0014(3) .12351(12) .43619(18) .0434(5) Uani d . 1 . . O H1WA -.047(6) .110(2) .495(4) .069(11) Uiso d . 1 . . H H1WB .059(7) .076(2) .416(4) .074(11) Uiso d . 1 . . H O2W .0000 -.2445(3) .2500 .1238(18) Uani d S 1 . . O H2WA -.1451 -.2321 .2136 .100 Uiso d . 1 . . H P1 .0000 .45753(5) .2500 .0331(3) Uani d S 1 . . P F1 .0000 .35438(12) .2500 .0437(5) Uani d S 1 . . F F2 .0000 .55917(14) .2500 .0610(6) Uani d S 1 . . F F3 .0436(3) .45621(10) .40178(13) .0532(5) Uani d . 1 . . F F4 .2650(2) .45701(10) .26905(15) .0523(4) Uani d . 1 . . F 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 .0279(8) .0322(9) .0258(8) -.0012(6) .0075(6) .0005(6) N2 .0326(9) .0330(9) .0257(8) .0021(7) .0096(7) .0023(7) O1 .0580(11) .0395(9) .0541(10) -.0102(7) .0317(9) .0014(7) O2 .0599(11) .0300(8) .0578(11) -.0040(7) .0233(9) .0021(7) C1 .0298(9) .0313(10) .0254(9) -.0001(8) .0053(8) .0009(8) C2 .0238(8) .0295(10) .0253(9) .0000(7) .0066(7) .0014(7) C3 .0288(9) .0297(10) .0213(9) .0016(7) .0073(7) .0025(7) C4 .0378(11) .0348(11) .0280(9) -.0044(9) .0102(8) .0000(8) C5 .0532(14) .0362(12) .0301(10) -.0089(10) .0073(10) -.0024(9) C6 .0590(14) .0384(12) .0253(10) .0030(10) .0112(9) -.0040(9) C7 .0472(12) .0390(12) .0259(9) .0067(10) .0155(9) .0021(8) C8 .0415(12) .0342(11) .0316(10) -.0045(9) .0088(9) .0030(8) O1W .0399(9) .0472(11) .0491(10) -.0032(7) .0223(8) .0074(8) O2W .089(3) .099(3) .182(6) .000 .037(3) .000 P1 .0331(4) .0381(5) .0288(5) .000 .0101(3) .000 F1 .0530(11) .0404(11) .0437(10) .000 .0233(9) .000 F2 .0629(14) .0399(12) .0721(15) .000 .0060(12) .000 F3 .0609(9) .0684(10) .0307(8) .0100(7) .0136(6) -.0075(6) F4 .0354(8) .0632(10) .0596(10) -.0034(6) .0153(7) -.0023(7) 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' P P .1023 .0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F .0171 .0103 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C2 N1 C1 . . 120.49(17) C7 N2 C3 . . 122.12(19) C7 N2 H2N . . 116.9(18) C3 N2 H2N . . 121.0(19) C8 O2 H2O . . 107(3) N1 C1 C1 . 2_655 118.69(12) N1 C1 C8 . . 112.74(17) C1 C1 C8 2_655 . 128.56(12) N1 C2 C2 . 2_655 118.84(11) N1 C2 C3 . . 115.22(16) C2 C2 C3 2_655 . 125.84(11) N2 C3 C4 . . 119.21(18) N2 C3 C2 . . 117.27(17) C4 C3 C2 . . 123.29(17) C3 C4 C5 . . 119.3(2) C3 C4 H4 . . 126.3(15) C5 C4 H4 . . 114.3(15) C6 C5 C4 . . 119.8(2) C6 C5 H5 . . 119.8(19) C4 C5 H5 . . 120.3(19) C7 C6 C5 . . 119.1(2) C7 C6 H6 . . 119.7(18) C5 C6 H6 . . 121.1(18) N2 C7 C6 . . 120.4(2) N2 C7 H7 . . 112.7(17) C6 C7 H7 . . 126.8(17) O1 C8 O2 . . 123.6(2) O1 C8 C1 . . 117.53(19) O2 C8 C1 . . 118.9(2) H1WA O1W H1WB . . 104(4) F3 P1 F3 2 . 178.51(13) F3 P1 F2 2 . 90.75(6) F3 P1 F2 . . 90.75(6) F3 P1 F4 2 2 89.88(8) F3 P1 F4 . 2 90.11(8) F2 P1 F4 . 2 90.30(7) F3 P1 F4 2 . 90.11(8) F3 P1 F4 . . 89.88(8) F2 P1 F4 . . 90.30(7) F4 P1 F4 2 . 179.41(13) F3 P1 F1 2 . 89.25(6) F3 P1 F1 . . 89.25(6) F2 P1 F1 . . 180.0 F4 P1 F1 2 . 89.70(7) F4 P1 F1 . . 89.70(7) 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 . 1.331(3) ? N1 C1 . 1.333(3) ? N2 C7 . 1.340(3) ? N2 C3 . 1.349(3) ? N2 H2N . .91(3) ? O1 C8 . 1.222(3) ? O2 C8 . 1.279(3) ? O2 H2O . 1.206(5) ? C1 C1 2_655 1.414(4) ? C1 C8 . 1.522(3) ? C2 C2 2_655 1.409(4) ? C2 C3 . 1.482(3) ? C3 C4 . 1.380(3) ? C4 C5 . 1.393(3) ? C4 H4 . 1.05(3) ? C5 C6 . 1.377(4) ? C5 H5 . .91(3) ? C6 C7 . 1.372(4) ? C6 H6 . .99(3) ? C7 H7 . .92(3) ? O1W H1WA . .79(4) ? O1W H1WB . .89(4) ? O2W H2WA . .8946 ? P1 F3 2 1.5897(14) ? P1 F3 . 1.5897(14) ? P1 F2 . 1.591(2) ? P1 F4 2 1.5948(14) ? P1 F4 . 1.5948(14) ? P1 F1 . 1.615(2) ? 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 O2 H2O O2 2_655 1.206(5) 1.206(5) 2.405(4) 171(6) N2 H2N O1W . .91(3) 1.77(3) 2.683(3) 177(3) O1W H1WA O1 3_556 .79(4) 1.98(4) 2.739(2) 160(4) O1W H1WB O1 . .89(4) 1.96(4) 2.841(3) 171(4) O2W H2WA O2 2 .89 2.07 2.815(4) 140 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion C2 N1 C1 C1 . 2_655 9.0(3) C2 N1 C1 C8 . . -169.71(17) C1 N1 C2 C2 . 2_655 9.2(3) C1 N1 C2 C3 . . -167.13(17) C7 N2 C3 C4 . . 1.0(3) C7 N2 C3 C2 . . 175.63(17) N1 C2 C3 N2 . . -30.2(2) C2 C2 C3 N2 2_655 . 153.7(2) N1 C2 C3 C4 . . 144.14(19) C2 C2 C3 C4 2_655 . -31.9(3) N2 C3 C4 C5 . . -.9(3) C2 C3 C4 C5 . . -175.14(19) C3 C4 C5 C6 . . .4(3) C4 C5 C6 C7 . . .0(3) C3 N2 C7 C6 . . -.7(3) C5 C6 C7 N2 . . .2(3) N1 C1 C8 O1 . . 13.5(3) C1 C1 C8 O1 2_655 . -165.0(3) N1 C1 C8 O2 . . -168.02(19) C1 C1 C8 O2 2_655 . 13.5(4)