#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012254.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2012254 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1184 _journal_page_last 1188 _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 ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Alfonso, Montserrat' 'Wang, Yi' 'Stoeckli-Evans, Helen' _chemical_formula_moiety 'C16 H10 N4 O4' _chemical_formula_sum 'C16 H10 N4 O4' _chemical_formula_weight 322.28 _symmetry_cell_setting monoclinic 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' _cell_length_a 10.4770(10) _cell_length_b 13.523(2) _cell_length_c 10.0580(10) _cell_angle_alpha 90 _cell_angle_beta 110.070(10) _cell_angle_gamma 90 _cell_volume 1338.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.599 _diffrn_ambient_temperature 293(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 O1 -.0606(2) .16027(19) .7237(2) .0590(7) Uani d . 1 . . O O2 -.1543(2) .26898(18) .5480(2) .0416(6) Uani d . 1 . . O O3 -.2703(2) .07332(17) .3870(2) .0471(7) Uani d . 1 . . O O4 -.26759(19) .13092(17) .1812(2) .0417(6) Uani d . 1 . . O N1 .1355(2) .16093(19) .5751(2) .0360(7) Uani d . 1 . . N N2 .0163(2) .10376(19) .2992(2) .0350(7) Uani d . 1 . . N N3 .4589(2) .12789(19) .5341(2) .0374(7) Uani d . 1 . . N N4 .3489(2) .09486(19) .2720(3) .0355(7) Uani d . 1 . . N C1 .0013(3) .1570(2) .5164(3) .0334(8) Uani d . 1 . . C C2 -.0600(3) .1244(2) .3771(3) .0319(8) Uani d . 1 . . C C3 .1531(3) .1131(2) .3540(3) .0291(8) Uani d . 1 . . C C4 .2148(3) .1377(2) .4983(3) .0309(8) Uani d . 1 . . C C5 .3616(3) .1443(2) .5897(3) .0312(7) Uani d . 1 . . C C6 .3982(3) .1669(3) .7323(3) .0415(9) Uani d . 1 . . C C7 .5345(3) .1726(3) .8139(4) .0449(9) Uani d . 1 . . C C8 .6322(3) .1562(3) .7545(3) .0415(9) Uani d . 1 . . C C9 .5914(3) .1339(3) .6132(3) .0396(9) Uani d . 1 . . C C10 .2126(3) .0967(2) .2395(3) .0328(8) Uani d . 1 . . C C11 .1310(3) .0839(3) .0996(3) .0427(9) Uani d . 1 . . C C12 .1874(3) .0685(3) -.0032(4) .0474(10) Uani d . 1 . . C C13 .3273(3) .0655(3) .0342(3) .0429(9) Uani d . 1 . . C C14 .4054(3) .0804(3) .1723(3) .0420(9) Uani d . 1 . . C C15 -.0765(3) .1949(3) .6078(3) .0383(9) Uani d . 1 . . C C16 -.2119(3) .1083(2) .3103(3) .0335(8) Uani d . 1 . . C H2O -.200(4) .315(3) .623(4) .095(13) Uiso d . 1 . . H H3N .419(3) .112(2) .407(3) .071(11) Uiso d . 1 . . H H6 .326(3) .171(2) .768(3) .044(9) Uiso d . 1 . . H H7 .561(2) .1891(19) .912(3) .028(8) Uiso d . 1 . . H H8 .723(3) .1572(19) .805(3) .025(8) Uiso d . 1 . . H H9 .659(3) .120(2) .560(3) .059(10) Uiso d . 1 . . H H11 .034(3) .087(2) .074(3) .056(10) Uiso d . 1 . . H H12 .127(3) .059(2) -.104(3) .063(10) Uiso d . 1 . . H H13 .368(3) .052(2) -.035(3) .039(9) Uiso d . 1 . . H H14 .515(3) .076(2) .207(3) .065(10) Uiso d . 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 O1 .0600(16) .088(2) .0356(14) .0218(15) .0250(12) .0141(14) O2 .0344(13) .0594(17) .0292(13) .0129(12) .0088(11) -.0012(12) O3 .0373(13) .0647(18) .0432(13) -.0069(12) .0188(11) .0060(13) O4 .0267(12) .0652(17) .0311(13) -.0086(11) .0073(10) .0025(12) N1 .0257(15) .0509(19) .0301(15) .0025(13) .0079(12) .0009(13) N2 .0279(15) .0460(19) .0315(14) .0005(12) .0109(12) -.0058(13) N3 .0264(16) .057(2) .0270(14) -.0026(13) .0068(12) -.0029(14) N4 .0258(15) .0508(19) .0292(15) -.0008(13) .0086(12) -.0044(13) C1 .0287(17) .044(2) .0300(17) .0042(16) .0130(14) .0040(16) C2 .0282(17) .035(2) .0336(18) .0023(15) .0127(14) .0007(15) C3 .0257(17) .033(2) .0292(17) -.0005(14) .0098(14) -.0034(15) C4 .0229(16) .036(2) .0336(17) .0007(14) .0092(14) .0017(15) C5 .0289(18) .034(2) .0304(17) -.0001(15) .0094(14) .0016(15) C6 .033(2) .057(3) .035(2) .0019(17) .0117(17) .0005(18) C7 .039(2) .062(3) .0295(19) .0001(18) .0064(17) -.0061(19) C8 .0265(19) .054(2) .037(2) -.0026(18) .0015(16) .0003(18) C9 .0227(18) .056(3) .0390(19) -.0007(16) .0095(16) .0018(18) C10 .0275(18) .040(2) .0319(18) .0013(15) .0112(14) .0005(16) C11 .0285(19) .065(3) .0338(19) .0040(18) .0101(17) -.0053(17) C12 .035(2) .074(3) .032(2) .0027(19) .0102(17) -.0065(19) C13 .045(2) .057(3) .034(2) .0038(18) .0224(18) -.0040(18) C14 .0323(19) .058(3) .041(2) .0000(18) .0197(17) -.0051(18) C15 .0217(18) .057(3) .0338(19) -.0012(17) .0067(15) -.0041(18) C16 .0276(17) .038(2) .0385(19) .0002(15) .0163(16) -.0019(16) 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 O1 C15 . 1.214(3) ? O2 C15 . 1.301(4) ? O2 H2O . 1.20(4) ? O3 C16 . 1.231(3) ? O4 C16 . 1.265(3) ? N1 C1 . 1.326(4) ? N1 C4 . 1.352(3) ? N2 C2 . 1.327(3) ? N2 C3 . 1.354(3) ? N3 C5 . 1.338(3) ? N3 C9 . 1.345(3) ? N3 H3N . 1.22(3) ? N4 C14 . 1.342(3) ? N4 C10 . 1.351(3) ? N4 H3N . 1.32(3) ? C1 C2 . 1.398(4) ? C1 C15 . 1.512(4) ? C2 C16 . 1.516(4) ? C3 C4 . 1.411(4) ? C3 C10 . 1.502(4) ? C4 C5 . 1.499(4) ? C5 C6 . 1.386(4) ? C6 C7 . 1.383(4) ? C6 H6 . .94(3) ? C7 C8 . 1.368(4) ? C7 H7 . .96(2) ? C8 C9 . 1.370(4) ? C8 H8 . .91(2) ? C9 H9 . 1.03(3) ? C10 C11 . 1.384(4) ? C11 C12 . 1.372(4) ? C11 H11 . .95(3) ? C12 C13 . 1.383(4) ? C12 H12 . 1.00(3) ? C13 C14 . 1.364(4) ? C13 H13 . .95(3) ? C14 H14 . 1.08(3) ?