#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006910.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_2006910 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1998 _journal_volume 54 _journal_page_first 140 _journal_page_last 142 _publ_section_title ; 4,9-Dihydroxy-4,9-dimethyl-4H,9H-1,2,5,6,6a,7,8-hepta\-hydro\-imidazo- [1,2,3-i,j][1,8]naphthyridinium Benzoate ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _[local]_cod_cif_authors_sg_H-M 'P 21/n' loop_ _publ_author_name 'Zhang, Jian-Heng' 'Chen, Xue-An' 'Li, Yan' 'Huang, Zhi-Tang' _chemical_formula_moiety 'C12 H21 N2 O2 +,C7 H5 O2 -' _chemical_formula_sum 'C19 H26 N2 O4' _chemical_formula_iupac 'C12 H21 N2 O2 +,C7 H5 O2 -' _chemical_formula_weight 346.42 _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.210(3) _cell_length_b 9.801(3) _cell_length_c 13.968(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.728(12) _cell_angle_gamma 90.00 _cell_volume 1807.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _exptl_crystal_density_diffrn 1.273 _refine_ls_R_factor_obs .0441 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O(1) .50899(11) .0241(2) .63311(11) .0713(5) Uani d . 1 . O H(O1) .47545(11) .0861(2) .65554(11) .133(10) Uiso calc R 1 . H O(2) .32291(11) .0618(2) .98743(10) .0644(4) Uani d . 1 . O H(O2) .32850(11) .1214(2) .94678(10) .133(10) Uiso calc R 1 . H O(3) .41551(11) .2747(2) .90726(11) .0684(5) Uani d . 1 . O O(4) .42953(11) .1807(2) .76524(12) .0766(5) Uani d . 1 . O N(1) .35895(11) -.1066(2) .87333(11) .0496(4) Uani d . 1 . N N(2) .43291(12) -.1314(2) .73580(11) .0515(4) Uani d . 1 . N C(1) .4617(2) -.1521(3) .9006(2) .0766(8) Uani d . 1 . C H(1A) .4606(2) -.2418(3) .9298(2) .077(2) Uiso calc R 1 . H H(1B) .4943(2) -.0884(3) .9448(2) .077(2) Uiso calc R 1 . H C(2) .5146(2) -.1555(3) .80716(15) .0737(7) Uani d . 1 . C H(2A) .5657(2) -.0847(3) .80463(15) .077(2) Uiso calc R 1 . H H(2B) .5463(2) -.2434(3) .79727(15) .077(2) Uiso calc R 1 . H C(3) .5190(2) -.2068(3) .5926(2) .0877(8) Uani d . 1 . C H(3A) .4838(2) -.2925(3) .5922(2) .104(4) Uiso calc R 1 . H H(3B) .5804(2) -.2149(3) .6306(2) .104(4) Uiso calc R 1 . H H(3C) .5348(2) -.1822(3) .5283(2) .104(4) Uiso calc R 1 . H C(4) .4528(2) -.0983(2) .63472(15) .0606(6) Uani d . 1 . C C(5) .3519(2) -.0847(2) .58045(14) .0658(6) Uani d . 1 . C H(5A) .3223(2) -.1746(2) .57190(14) .077(2) Uiso calc R 1 . H H(5B) .3635(2) -.0473(2) .51744(14) .077(2) Uiso calc R 1 . H C(6) .2776(2) .0061(2) .63142(14) .0623(6) Uani d . 1 . C H(6A) .2153(2) .0134(2) .59327(14) .077(2) Uiso calc R 1 . H H(6B) .3060(2) .0968(2) .63913(14) .077(2) Uiso calc R 1 . H C(7) .25520(14) -.0532(2) .72901(13) .0482(5) Uani d . 1 . C H(7) .21576(14) -.1366(2) .71732(13) .054(5) Uiso calc R 1 . H C(8) .34961(13) -.0950(2) .77973(13) .0425(5) Uani d . 1 . C C(9) .19393(15) .0351(2) .79517(15) .0587(6) Uani d . 1 . C H(9A) .12717(15) .0512(2) .76660(15) .077(2) Uiso calc R 1 . H H(9B) .22715(15) .1226(2) .80440(15) .077(2) Uiso calc R 1 . H C(10) .18418(15) -.0361(2) .89135(15) .0605(6) Uani d . 1 . C H(10A) .14100(15) .0182(2) .93141(15) .077(2) Uiso calc R 1 . H H(10B) .15155(15) -.1238(2) .88109(15) .077(2) Uiso calc R 1 . H C(11) .2773(2) -.1621(2) 1.0227(2) .0731(7) Uani d . 1 . C H(11A) .2518(2) -.2463(2) .9965(2) .104(4) Uiso calc R 1 . H H(11B) .2320(2) -.1290(2) 1.0699(2) .104(4) Uiso calc R 1 . H H(11C) .3431(2) -.1770(2) 1.0520(2) .104(4) Uiso calc R 1 . H C(12) .28525(15) -.0583(2) .94370(14) .0524(5) Uani d . 1 . C C(13) .4582(2) .2621(2) .8294(2) .0510(5) Uani d . 1 . C C(14) .54745(14) .3531(2) .81057(14) .0483(5) Uani d . 1 . C C(15) .6029(2) .3393(2) .7291(2) .0664(6) Uani d . 1 . C H(15) .5830(2) .2752(2) .6832(2) .083(3) Uiso calc R 1 . H C(16) .6869(2) .4182(3) .7144(2) .0868(8) Uani d . 1 . C H(16) .7238(2) .4066(3) .6593(2) .083(3) Uiso calc R 1 . H C(17) .7162(2) .5138(3) .7809(2) .0883(8) Uani d . 1 . C H(17) .7733(2) .5669(3) .7711(2) .083(3) Uiso calc R 1 . H C(18) .6617(2) .5316(3) .8619(2) .0785(8) Uani d . 1 . C H(18) .6812(2) .5976(3) .9066(2) .083(3) Uiso calc R 1 . H C(19) .5777(2) .4512(2) .8769(2) .0615(6) Uani d . 1 . C H(19) .5410(2) .4631(2) .9321(2) .083(3) Uiso calc R 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 O(1) .0659(10) .0744(11) .0748(10) -.0205(9) .0198(8) -.0051(9) O(2) .0740(10) .0658(10) .0538(8) -.0162(8) .0070(7) -.0055(8) O(3) .0655(10) .0779(11) .0621(9) -.0106(8) .0060(8) .0063(8) O(4) .0648(10) .0762(11) .0889(11) -.0190(9) .0071(8) -.0266(10) N(1) .0404(9) .0618(11) .0464(10) .0043(8) -.0028(7) .0042(8) N(2) .0428(9) .0589(11) .0529(10) .0017(9) .0025(8) .0007(9) C(1) .0550(14) .108(2) .0662(14) .0184(15) -.0125(12) .0074(15) C(2) .0460(12) .096(2) .079(2) .0153(13) -.0010(12) .0095(14) C(3) .089(2) .083(2) .093(2) -.004(2) .034(2) -.016(2) C(4) .0630(14) .0634(15) .0560(13) -.0119(13) .0138(11) -.0056(11) C(5) .079(2) .069(2) .0496(12) -.0178(14) -.0002(12) -.0022(11) C(6) .0632(14) .0645(15) .0578(14) -.0090(13) -.0185(11) .0097(12) C(7) .0408(11) .0473(12) .0560(12) -.0033(10) -.0090(9) .0021(10) C(8) .0383(11) .0398(11) .0491(11) -.0044(9) -.0020(9) .0004(9) C(9) .0418(11) .0562(13) .0774(15) .0095(11) -.0075(10) -.0013(12) C(10) .0470(12) .0624(14) .0727(14) -.0004(11) .0116(11) -.0056(12) C(11) .090(2) .068(2) .0623(14) -.0126(14) .0125(13) .0065(12) C(12) .0510(12) .0547(13) .0519(12) -.0066(11) .0074(10) .0001(11) C(13) .0440(12) .0479(13) .0606(13) .0053(11) -.0041(10) .0031(11) C(14) .0414(11) .0437(12) .0592(13) .0026(10) -.0063(10) .0068(10) C(15) .0602(14) .0610(15) .078(2) -.0037(12) .0090(13) -.0037(13) C(16) .071(2) .081(2) .110(2) -.013(2) .029(2) .000(2) C(17) .061(2) .076(2) .128(2) -.0197(15) .003(2) .011(2) C(18) .081(2) .060(2) .093(2) -.0170(15) -.030(2) .0051(15) C(19) .0642(14) .0569(14) .0627(14) -.0043(12) -.0102(11) .0029(12) 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 O(1) C(4) . 1.411(3) no O(2) C(12) . 1.410(2) no O(3) C(13) . 1.246(2) yes O(4) C(13) . 1.250(2) yes N(1) C(8) . 1.314(2) yes N(1) C(1) . 1.468(2) yes N(1) C(12) . 1.482(2) yes N(2) C(8) . 1.325(2) yes N(2) C(2) . 1.466(2) yes N(2) C(4) . 1.480(2) yes C(1) C(2) . 1.499(3) no C(3) C(4) . 1.507(3) no C(4) C(5) . 1.519(3) no C(5) C(6) . 1.518(3) no C(6) C(7) . 1.519(3) no C(7) C(8) . 1.474(2) yes C(7) C(9) . 1.517(3) no C(9) C(10) . 1.523(3) no C(10) C(12) . 1.518(3) no C(11) C(12) . 1.507(3) no C(13) C(14) . 1.508(3) no C(14) C(15) . 1.379(3) yes C(14) C(19) . 1.385(3) yes C(15) C(16) . 1.373(3) yes C(16) C(17) . 1.367(4) yes C(17) C(18) . 1.370(3) yes C(18) C(19) . 1.383(3) yes