#------------------------------------------------------------------------------ #$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2008997.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_2008997 _journal_name_full 'Acta Crystallographica' _journal_year 1999 _journal_volume C55 _journal_page_first 1704 _journal_page_last 1706 _publ_section_title ; A zwitterionic Meisenheimer complex of 2,4,6-trinitrobenzene ; loop_ _publ_author_name 'Borbulevych, Oleg Ya.' 'Shishkin, Oleg V.' 'Knyazev, Victor N.' _chemical_formula_sum 'C14 H12 N4 O8' _chemical_formula_weight 364.28 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/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' '-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 13.336(3) _cell_length_b 13.837(3) _cell_length_c 16.059(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.51(2) _cell_angle_gamma 90.00 _cell_volume 2930.8(12) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _exptl_crystal_density_diffrn 1.651 _diffrn_ambient_temperature 193(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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 .65859(9) -.04326(8) .79654(7) .0246(2) Uani d . 1 . N N2 .63312(10) .25567(8) .94478(7) .0277(2) Uani d . 1 . N N3 .63088(9) .27438(8) .64344(7) .0273(2) Uani d . 1 . N N4 .90383(8) .10984(7) .58624(6) .0199(2) Uani d . 1 . N O1 .66936(9) -.08960(7) .73284(7) .0351(3) Uani d . 1 . O O2 .65380(10) -.08355(7) .86478(7) .0392(3) Uani d . 1 . O O3 .64233(11) .20693(8) 1.01003(7) .0398(3) Uani d . 1 . O O4 .62230(10) .34494(8) .94569(7) .0403(3) Uani d . 1 . O O5 .60741(10) .36071(8) .64762(7) .0417(3) Uani d . 1 . O O6 .64992(10) .23737(8) .57725(6) .0363(3) Uani d . 1 . O O7 .75240(6) .09313(6) .68168(5) .0201(2) Uani d . 1 . O O8 .58140(6) .06782(7) .64374(5) .0235(2) Uani d . 1 . O C1 .65473(9) .10845(8) .70769(7) .0181(2) Uani d . 1 . C C2 .65128(9) .06079(8) .79178(7) .0194(2) Uani d . 1 . C C3 .64514(9) .10760(8) .86514(8) .0200(2) Uani d . 1 . C H3 .6474(13) .0732(12) .9175(11) .025(4) Uiso d . 1 . H C4 .63647(10) .20832(8) .86653(8) .0213(2) Uani d . 1 . C C5 .62954(10) .26121(9) .79190(8) .0223(2) Uani d . 1 . C H5 .6191(15) .3323(15) .7926(11) .035(5) Uiso d . 1 . H C6 .63690(10) .21564(8) .71763(8) .0210(2) Uani d . 1 . C C7 .74369(9) .03063(9) .60992(8) .0212(2) Uani d . 1 . C H7 .7737(13) -.0350(12) .6277(11) .026(4) Uiso d . 1 . H C8 .62901(10) .02521(11) .57849(9) .0268(3) Uani d . 1 . C H8B .6097(14) .0633(14) .5286(12) .034(4) Uiso d . 1 . H H8A .6049(14) -.0408(14) .5721(11) .029(4) Uiso d . 1 . H C9 .80387(10) .07333(10) .54507(8) .0236(2) Uani d . 1 . C H9B .8164(13) .0279(12) .5037(11) .025(4) Uiso d . 1 . H H9A .7697(15) .1269(14) .5175(12) .034(5) Uiso d . 1 . H C10 .91369(10) .20475(9) .60480(8) .0223(2) Uani d . 1 . C H10 .8558(14) .2411(13) .5891(10) .029(4) Uiso d . 1 . H C11 1.00434(10) .24104(9) .64417(8) .0254(3) Uani d . 1 . C H11 1.0101(14) .3091(15) .6544(12) .037(5) Uiso d . 1 . H C12 1.08555(10) .17945(10) .66638(9) .0276(3) Uani d . 1 . C H12 1.1436(14) .2040(13) .6930(11) .028(4) Uiso d . 1 . H C13 1.07329(11) .08153(10) .64889(10) .0309(3) Uani d . 1 . C H13 1.1269(16) .0332(15) .6675(12) .042(5) Uiso d . 1 . H C14 .98191(10) .04813(9) .60806(9) .0261(3) Uani d . 1 . C H14 .9687(14) -.0187(13) .5931(11) .034(5) 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 N1 .0288(5) .0162(4) .0285(6) -.0029(4) .0038(4) .0002(4) N2 .0358(6) .0242(5) .0251(5) .0037(4) .0105(5) -.0023(4) N3 .0337(6) .0225(5) .0254(5) .0039(4) .0030(5) .0056(4) N4 .0198(5) .0213(5) .0195(5) -.0004(4) .0058(4) -.0007(4) O1 .0510(7) .0191(4) .0365(6) -.0018(4) .0107(5) -.0059(4) O2 .0640(8) .0197(5) .0348(6) -.0045(5) .0099(5) .0074(4) O3 .0671(8) .0323(5) .0231(5) .0019(5) .0167(5) .0004(4) O4 .0638(8) .0233(5) .0353(6) .0109(5) .0121(5) -.0066(4) O5 .0624(8) .0252(5) .0379(6) .0149(5) .0087(5) .0116(4) O6 .0554(7) .0332(5) .0210(5) .0065(5) .0078(4) .0044(4) O7 .0165(4) .0240(4) .0205(4) -.0019(3) .0046(3) -.0041(3) O8 .0169(4) .0308(5) .0226(4) -.0024(3) .0026(3) -.0073(4) C1 .0174(5) .0185(5) .0186(5) -.0009(4) .0035(4) -.0022(4) C2 .0197(5) .0144(5) .0247(6) -.0014(4) .0053(4) .0007(4) C3 .0216(5) .0181(5) .0213(5) -.0005(4) .0065(4) .0023(4) C4 .0249(6) .0191(5) .0210(5) .0021(4) .0069(4) -.0014(4) C5 .0243(6) .0164(5) .0263(6) .0033(4) .0039(5) .0008(4) C6 .0246(6) .0173(5) .0209(5) .0017(4) .0031(4) .0041(4) C7 .0229(6) .0197(5) .0219(5) -.0006(4) .0058(4) -.0027(4) C8 .0227(6) .0336(7) .0242(6) -.0052(5) .0043(5) -.0100(5) C9 .0211(6) .0291(6) .0209(6) -.0029(5) .0034(4) -.0025(5) C10 .0269(6) .0189(5) .0216(6) .0024(4) .0056(5) .0026(4) C11 .0300(6) .0208(6) .0260(6) -.0030(5) .0062(5) .0002(5) C12 .0222(6) .0290(6) .0309(7) -.0050(5) .0014(5) .0008(5) C13 .0235(6) .0268(6) .0422(8) .0039(5) .0043(5) .0027(6) C14 .0244(6) .0190(5) .0359(7) .0021(5) .0074(5) -.0006(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 N1 O1 . . 1.2336(15) yes N1 O2 . . 1.2395(15) yes N1 C2 . . 1.444(2) yes N2 O3 . . 1.237(2) yes N2 O4 . . 1.244(2) yes N2 C4 . . 1.424(2) yes N3 O5 . . 1.239(2) yes N3 O6 . . 1.240(2) yes N3 C6 . . 1.435(2) yes N4 C10 . . 1.349(2) yes N4 C14 . . 1.352(2) yes N4 C9 . . 1.486(2) yes O7 C7 . . 1.4318(14) yes O7 C1 . . 1.4413(14) yes O8 C1 . . 1.4247(14) yes O8 C8 . . 1.430(2) yes C1 C2 . . 1.510(2) yes C1 C6 . . 1.514(2) yes C2 C3 . . 1.357(2) yes C3 C4 . . 1.399(2) yes C4 C5 . . 1.396(2) yes C5 C6 . . 1.365(2) yes C7 C9 . . 1.525(2) no C7 C8 . . 1.540(2) yes C10 C11 . . 1.374(2) no C11 C12 . . 1.383(2) no C12 C13 . . 1.389(2) no C13 C14 . . 1.376(2) no