#------------------------------------------------------------------------------ #$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012255.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_2012255 _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 15 _symmetry_space_group_name_Hall '-I 2ya' _symmetry_space_group_name_H-M 'I 1 2/a 1' _[local]_cod_cif_authors_sg_H-M 'I 2/a' loop_ _publ_author_name 'Alfonso, Montserrat' 'Wang, Yi' 'Stoeckli-Evans, Helen' _chemical_formula_moiety 'C16 H11 N4 O4 + , Cl - , 2.25H2 O' _chemical_formula_sum 'C16 H15.5 Cl N4 O6.25' _chemical_formula_weight 399.27 _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 19.5883(17) _cell_length_b 8.0623(5) _cell_length_c 22.936(2) _cell_angle_alpha 90 _cell_angle_beta 90.559(11) _cell_angle_gamma 90 _cell_volume 3622.0(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.464 _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 .00022(9) .1926(2) .33297(7) .0504(5) Uani d . 1 . . O O2 -.04931(9) .4384(2) .31389(8) .0468(4) Uani d . 1 . . O H2O -.0711(17) .427(4) .3513(16) .098(11) Uiso d . 1 . . H O3 -.12559(9) .1414(3) .14811(8) .0677(6) Uani d . 1 . . O O4 -.12505(7) .1999(2) .24294(7) .0445(4) Uani d . 1 . . O N1 .07729(9) .3448(2) .23364(8) .0335(5) Uani d . 1 . . N N2 -.00305(9) .2937(2) .13643(8) .0332(4) Uani d . 1 . . N N3 .20722(9) .4782(3) .21689(8) .0362(5) Uani d . 1 . . N H3N .1784(14) .552(4) .2371(11) .059(8) Uiso d . 1 . . H N4 .04464(11) .2977(3) .02828(8) .0419(5) Uani d . 1 . . N H4N .0143(14) .218(4) .0390(11) .056(9) Uiso d . 1 . . H C1 .01098(10) .3102(3) .23847(9) .0299(5) Uani d . 1 . . C C2 -.02847(10) .2726(3) .18944(9) .0315(5) Uani d . 1 . . C C3 .06192(11) .3391(3) .13071(9) .0327(5) Uani d . 1 . . C C4 .10405(10) .3533(3) .17995(9) .0316(5) Uani d . 1 . . C C5 .17977(11) .3684(3) .17965(10) .0347(5) Uani d . 1 . . C C6 .22210(13) .2671(4) .14841(12) .0462(7) Uani d . 1 . . C H6 .2041(12) .194(3) .1250(11) .043(8) Uiso d . 1 . . H C7 .29176(13) .2780(4) .15607(13) .0529(7) Uani d . 1 . . C H7 .3200(15) .208(4) .1362(12) .068(9) Uiso d . 1 . . H C8 .31845(13) .3931(4) .19409(12) .0492(7) Uani d . 1 . . C H8 .3652(14) .403(3) .2006(10) .051(7) Uiso d . 1 . . H C9 .27469(12) .4937(4) .22394(12) .0438(7) Uani d . 1 . . C H9 .2894(12) .575(3) .2516(11) .043(7) Uiso d . 1 . . H C10 .08151(12) .3768(3) .06990(10) .0367(6) Uani d . 1 . . C C11 .12867(14) .4934(4) .05341(12) .0500(7) Uani d . 1 . . C H11 .1562(14) .547(4) .0826(12) .060(8) Uiso d . 1 . . H C12 .13715(17) .5273(5) -.00524(13) .0633(9) Uani d . 1 . . C H12 .1709(15) .608(4) -.0163(12) .063(8) Uiso d . 1 . . H C13 .09857(17) .4461(4) -.04616(13) .0629(9) Uani d . 1 . . C H14 .0993(16) .469(4) -.0863(15) .089(10) Uiso d . 1 . . H C14 .05233(17) .3294(4) -.02876(12) .0562(8) Uani d . 1 . . C H13 .0220(14) .270(4) -.0548(12) .064(9) Uiso d . 1 . . H C15 -.01420(11) .3048(3) .30038(10) .0357(6) Uani d . 1 . . C C16 -.09956(11) .1984(3) .19289(11) .0389(6) Uani d . 1 . . C Cl1 .12673(3) .94713(9) .07395(3) .0540(2) Uani d . 1 . . Cl O1W .44735(11) .9286(3) .04654(11) .0664(6) Uani d . 1 . . O H1A .4215(18) .931(4) .0177(16) .084(12) Uiso d . 1 . . H H1B .4188(19) .899(5) .0784(18) .106(13) Uiso d . 1 . . H O2W .2565(4) .7120(7) .1020(5) .089(3) Uani d P .62(2) A 1 O H21 .228(4) .789(11) .088(3) .09(2) Uiso d P .62(2) A 1 H H22 .288(4) .774(10) .107(4) .11(3) Uiso d P .62(2) A 1 H O3W .2358(5) .770(2) .1446(9) .115(8) Uani d P .38(2) A 2 O H31 .286(5) .786(10) .145(4) .06(2) Uiso d P .38(2) A 2 H H32 .210(6) .846(15) .115(7) .11(4) Uiso d P .38(2) A 2 H O4W .2500 .1391(9) .0000 .137(4) Uani d SP .50 B 2 O H41 .2187 .0920 .0189 .100 Uiso d P .50 C 2 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 .0583(11) .0532(13) .0397(10) .0104(9) .0035(8) .0102(9) O2 .0603(11) .0369(11) .0434(10) .0024(9) .0184(8) .0000(8) O3 .0412(10) .1094(19) .0523(12) -.0232(11) -.0046(9) -.0108(11) O4 .0344(9) .0507(12) .0484(10) -.0046(8) .0079(7) .0039(8) N1 .0317(10) .0371(13) .0316(10) -.0004(9) .0024(8) -.0011(8) N2 .0316(10) .0360(13) .0322(10) .0009(9) -.0007(8) .0001(9) N3 .0273(10) .0426(14) .0386(11) .0000(9) .0024(8) -.0017(10) N4 .0490(12) .0445(15) .0321(11) .0066(11) .0014(9) -.0029(10) C1 .0300(12) .0264(14) .0333(12) .0007(10) .0034(9) .0015(10) C2 .0288(11) .0315(15) .0341(13) .0022(9) .0005(10) .0024(10) C3 .0344(12) .0299(14) .0337(12) .0022(10) .0033(9) -.0003(10) C4 .0296(11) .0314(15) .0338(12) -.0002(10) .0024(9) -.0014(10) C5 .0313(12) .0395(15) .0333(12) .0002(11) .0031(9) .0026(11) C6 .0408(15) .0471(19) .0509(16) .0011(13) .0116(12) -.0069(14) C7 .0398(15) .052(2) .0667(19) .0112(14) .0168(13) .0061(15) C8 .0282(13) .056(2) .0635(18) .0039(13) .0038(12) .0153(15) C9 .0322(13) .0515(19) .0477(15) -.0048(12) -.0025(11) .0044(13) C10 .0372(12) .0394(15) .0334(13) .0061(11) .0026(10) .0007(11) C11 .0477(16) .055(2) .0471(16) -.0023(14) .0053(13) .0104(14) C12 .0627(19) .070(2) .0571(19) .0060(17) .0208(15) .0231(17) C13 .077(2) .075(2) .0372(16) .0269(19) .0155(16) .0134(17) C14 .072(2) .063(2) .0329(15) .0233(17) -.0009(14) -.0036(14) C15 .0331(12) .0373(16) .0365(13) -.0036(11) .0018(10) -.0006(12) C16 .0286(12) .0420(16) .0460(15) .0017(11) -.0025(11) .0027(12) Cl1 .0539(4) .0623(5) .0460(4) .0026(3) .0048(3) -.0016(3) O1W .0630(13) .0796(17) .0565(13) .0058(11) -.0065(12) .0218(12) O2W .062(4) .065(4) .141(7) .009(3) -.028(4) -.007(3) O3W .057(6) .137(12) .150(14) -.001(5) -.008(6) .077(11) O4W .159(7) .069(5) .187(8) .000 .151(7) .000 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 . 1.205(3) ? O2 C15 . 1.317(3) ? O2 H2O . .97(4) ? O3 C16 . 1.231(3) ? O4 C16 . 1.256(3) ? N1 C1 . 1.334(3) ? N1 C4 . 1.345(3) ? N2 C2 . 1.329(3) ? N2 C3 . 1.332(3) ? N3 C9 . 1.336(3) ? N3 C5 . 1.339(3) ? N3 H3N . .94(3) ? N4 C14 . 1.343(3) ? N4 C10 . 1.351(3) ? N4 H4N . .91(3) ? C1 C2 . 1.392(3) ? C1 C15 . 1.508(3) ? C2 C16 . 1.518(3) ? C3 C4 . 1.397(3) ? C3 C10 . 1.482(3) ? C4 C5 . 1.488(3) ? C5 C6 . 1.371(3) ? C6 C7 . 1.377(4) ? C6 H6 . .87(3) ? C7 C8 . 1.373(4) ? C7 H7 . .92(3) ? C8 C9 . 1.369(4) ? C8 H8 . .93(3) ? C9 H9 . .95(3) ? C10 C11 . 1.373(4) ? C11 C12 . 1.384(4) ? C11 H11 . .96(3) ? C12 C13 . 1.366(5) ? C12 H12 . .96(3) ? C13 C14 . 1.368(5) ? C13 H14 . .94(3) ? C14 H13 . .96(3) ? O1W H1A . .83(4) ? O1W H1B . .95(4) ? O2W H21 . .89(9) ? O2W H22 . .81(9) ? O2W H31 . 1.29(8) ? O2W H32 . 1.45(12) ? O3W H21 . 1.32(6) ? O3W H22 . 1.34(7) ? O3W H31 . 1.00(10) ? O3W H32 . 1.05(14) ? O4W H41 . .8444 ? _cod_database_code 2012255