#------------------------------------------------------------------------------ #$Date: 2008-11-20 20:58:43 +0100 (Thu, 20 Nov 2008) $ #$Revision: 481 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006163.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_2006163 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1997 _journal_volume 53 _journal_page_first 646 _journal_page_last 648 _publ_section_title ; Anthranilic Acid--Picric Acid (2/1) Complex ; loop_ _publ_author_name 'In, Yasuko' 'Nagata, Hiroomi' 'Doi, Mitsunobu' 'Ishida, Toshimasa' 'Wakahara, Akio' _chemical_formula_moiety 'C20 H17 N5 O11' _chemical_formula_sum 'C20 H17 N5 O11' _chemical_formula_iupac '2C7 H7 N O2, C6 H3 N3 O7' _chemical_formula_weight 503.81 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 'x,-y,z+1/2' 'x-1/2,y-1/2,z' 'x-1/2,-y+1/2,z-1/2' _cell_length_a 10.356(2) _cell_length_b 15.350(3) _cell_length_c 13.394(3) _cell_angle_alpha 90 _cell_angle_beta 96.38(4) _cell_angle_gamma 90 _cell_volume 2116.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _exptl_crystal_density_diffrn 1.580(2) _exptl_crystal_density_meas 1.579 _refine_ls_R_factor_obs .059 _refine_ls_wR_factor_obs .067 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv C(1) .0446 .0692(6) .1010 .044(5) O(1) .0720(10) .0201(4) .1885(7) .073(3) C(2) .0090(10) .0223(3) .0080(10) .038(3) N(2) .0110(10) -.0732(3) .0120(10) .052(3) O(2) .0290(10) -.1120(4) .0895(8) .063(4) O(2') -.0180(10) -.1077(6) -.0710(10) .094(7) C(3) -.0268(7) .0610(6) -.0799(6) .038(4) C(4) -.0240(10) .1562(7) -.0773(9) .043(5) N(4) -.0590(10) .2036(6) -.1666(9) .059(6) O(4) -.1240(10) .1703(7) -.2377(8) .092(7) O(4') -.0290(10) .2782(7) -.1720(10) .106(8) C(5) .0090(10) .2014(3) .0090(10) .045(3) C(6) .0460(10) .1552(5) .0966(9) .042(5) N(6) .0830(10) .2044(5) .1931(9) .051(5) O(6) .0470(10) .2802(5) .1947(9) .076(5) O(6') .1470(10) .1661(6) .2588(8) .091(6) C(1A) -.2890(10) .0916(7) .0840(10) .046(5) C(1'A) -.2650(10) .1607(7) .1574(9) .043(5) O(1A) -.2810(10) .2378(5) .1432(8) .070(5) O(1'A) -.2120(10) .1357(5) .2456(8) .069(5) C(2A) -.3330(10) .1143(7) -.0140(10) .054(6) N(2A) -.3490(10) .1995(6) -.0530(9) .066(6) C(3A) -.3530(10) .0443(8) -.0865(9) .054(6) C(4A) -.3340(10) -.0419(8) -.0510(10) .066(7) C(5A) -.2970(10) -.0584(8) .0510(10) .066(7) C(6A) -.2710(10) .0048(7) .1140(10) .056(6) C(1B) .3120(10) .0948(6) -.0588(9) .043(5) C(1'B) .2840(10) .1608(6) -.1380(10) .057(6) O(1B) .3100(10) .2404(5) -.1174(8) .063(5) O(1'B) .2360(10) .1342(5) -.2265(8) .068(5) C(2B) .3520(10) .1118(8) .0430(10) .049(6) N(2B) .3640(10) .1939(7) .0730(10) .072(7) C(3B) .377(2) .0420(10) .1070(10) .082(9) C(4B) .363(2) -.0396(9) .0790(10) .076(8) C(5B) .3200(10) -.0612(7) -.0160(10) .066(7) C(6B) .2970(10) .0058(7) -.0890(10) .054(6) H(1) .1297 -.0344 .2185 .05 H(3) -.0570 .0266 -.1495 .00(3) H(5) .0049 .2670 .0013 .05(2) H(1'A) -.2162 .1783 .3061 .10(2) H(2aA) -.3887 .2076 -.1178 .09(3) H(2bA) -.3464 .2470 -.0011 .09(3) H(3A) -.3642 .0494 -.1571 .09(2) H(4A) -.3501 -.0935 -.1045 .06(2) H(5A) -.2930 -.1267 .0797 .10(2) H(6A) -.2326 -.0072 .1938 .04(3) H(1'B) .2186 .1783 -.2779 .09(2) H(2aB) .3633 .2388 .0274 .09(3) H(2bB) .4009 .2139 .1408 .06(3) H(3B) .4082 .0528 .1857 .05(2) H(4B) .3890 -.0908 .1327 .09(2) H(5B) .3014 -.1288 -.0359 .08(2) H(6B) .2572 -.0154 -.1645 .06(3) 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 C(1) .039(5) .052(5) .041(4) .015(4) -.011(4) -.004(4) O(1) .089(4) .068(3) .059(3) .004(3) .008(3) .010(3) C(2) .034(2) .034(3) .044(3) -.008(5) .003(2) -.010(5) N(2) .040(2) .038(2) .077(4) -.002(5) .004(2) -.007(6) O(2) .078(5) .034(3) .076(4) -.001(3) -.002(4) .017(3) O(2') .071(5) .071(6) .138(8) -.002(4) -.004(6) -.048(6) C(3) .043(5) .028(4) .043(4) .006(3) .016(4) -.004(3) C(4) .033(4) .063(6) .033(4) -.008(4) .004(4) .011(4) N(4) .066(6) .064(6) .046(5) .001(5) .015(4) .000(5) O(4) .131(8) .084(7) .059(5) .004(6) -.024(5) -.004(4) O(4') .140(10) .075(6) .099(8) -.033(6) -.021(7) .039(6) C(5) .039(2) .038(3) .056(3) .006(5) .005(2) .001(6) C(6) .049(5) .028(4) .049(5) -.012(4) .006(4) -.003(4) N(6) .053(5) .046(5) .053(5) -.012(4) -.007(4) -.016(4) O(6) .096(7) .045(4) .084(6) .008(4) -.020(5) -.029(4) O(6') .152(8) .072(5) .046(4) .011(6) -.027(5) -.016(4) C(1A) .039(5) .040(5) .057(6) .008(4) -.003(4) -.004(4) C(1'A) .045(5) .057(6) .025(4) .001(4) .010(4) .014(4) O(1A) .101(6) .050(5) .057(5) .013(4) -.011(4) -.004(4) O(1'A) .097(6) .049(4) .058(4) .010(4) .017(4) .000(4) C(2A) .049(6) .040(5) .072(7) .000(4) .017(5) -.017(5) N(2A) .085(7) .060(6) .053(5) .013(4) .016(5) .026(4) C(3A) .041(6) .091(8) .030(4) .011(5) .000(4) -.003(5) C(4A) .054(6) .051(7) .090(8) -.006(5) .015(6) -.031(7) C(5A) .052(7) .057(6) .088(7) -.005(5) .004(5) .016(6) C(6A) .032(4) .047(6) .087(7) .002(4) .013(5) -.006(5) C(1B) .042(5) .047(5) .040(4) .001(4) .014(4) -.003(4) C(1'B) .051(5) .028(5) .091(8) -.012(4) .004(5) .012(5) O(1B) .092(6) .038(4) .057(4) -.027(4) -.005(4) .000(3) O(1'B) .110(6) .050(4) .041(4) -.018(4) -.025(4) -.009(3) C(2B) .029(4) .074(8) .044(5) -.009(4) .000(4) -.010(5) N(2B) .085(7) .075(7) .056(6) -.025(5) -.019(5) .008(5) C(3B) .065(8) .090(10) .088(9) .019(7) .018(7) .031(8) C(4B) .061(7) .070(8) .096(9) .009(6) .007(7) .025(8) C(5B) .052(6) .044(5) .100(8) .013(5) .026(6) .037(5) C(6B) .061(6) .039(6) .062(6) .004(5) .011(5) -.001(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C(1) O(1) . . 1.395(9) yes C(1) C(2) . . 1.450(10) no C(1) C(6) . . 1.320(10) no C(2) N(2) . . 1.47(2) yes C(2) C(3) . . 1.330(10) no N(2) O(2) . . 1.190(10) yes N(2) O(2') . . 1.23(2) yes C(3) C(4) . . 1.460(10) no C(4) N(4) . . 1.41(2) no C(4) C(5) . . 1.36(2) no N(4) O(4) . . 1.22(2) yes N(4) O(4') . . 1.19(2) yes C(5) C(6) . . 1.39(2) no C(6) N(6) . . 1.51(2) yes N(6) O(6) . . 1.22(2) yes N(6) O(6') . . 1.20(2) yes C(1A) C(1'A) . . 1.44(2) yes C(1A) C(2A) . . 1.39(2) no C(1A) C(6A) . . 1.40(2) no C(1'A) O(1A) . . 1.21(2) yes C(1'A) O(1'A) . . 1.31(2) yes C(2A) N(2A) . . 1.41(2) yes C(2A) C(3A) . . 1.45(2) no C(3A) C(4A) . . 1.41(2) no C(4A) C(5A) . . 1.40(2) no C(5A) C(6A) . . 1.30(2) no C(1B) C(1'B) . . 1.48(2) yes C(1B) C(2B) . . 1.41(2) no C(1B) C(6B) . . 1.43(2) no C(1'B) O(1B) . . 1.28(2) yes C(1'B) O(1'B) . . 1.29(2) yes C(2B) N(2B) . . 1.32(2) yes C(2B) C(3B) . . 1.38(2) no C(3B) C(4B) . . 1.30(2) no C(4B) C(5B) . . 1.34(2) no C(5B) C(6B) . . 1.42(2) no