data_2200928 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2002 _journal_volume 58 _journal_page_first o102 _journal_page_last o104 _publ_section_title ; 1,4-Diazabicyclo[2.2.2]octanium 2,4-dinitrophenolate ; loop_ _publ_author_name 'Suchada Chantrapromma' 'Anwar Usman' 'Hoong-Kun Fun' 'Bo-Long Poh' 'Chatchanok Karalai' _chemical_formula_moiety 'C6 H13 N2 1+, C6 H3 N2 O5 1-' _chemical_formula_sum 'C12 H16 N4 O5' _chemical_formula_iupac 'C6 H13 N2 1+, C6 H3 N2 O5 1-' _chemical_formula_weight 296.29 _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 23.6934(4) _cell_length_b 6.4529(2) _cell_length_c 19.1830(5) _cell_angle_alpha 90.00 _cell_angle_beta 114.2470(10) _cell_angle_gamma 90.00 _cell_volume 2674.20(10) _cell_formula_units_Z 8 _cell_measurement_temperature 203(2) _exptl_crystal_density_diffrn 1.472 _diffrn_ambient_temperature 203(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 .58574(6) .2148(2) .35135(7) .0321(3) Uani d . 1 . . O O2 .68051(7) .2464(3) .49008(9) .0491(4) Uani d . 1 . . O O3 .66161(7) .2203(3) .58905(8) .0576(5) Uani d . 1 . . O O4 .46233(8) .2815(2) .58209(9) .0450(4) Uani d . 1 . . O O5 .38135(8) .2617(3) .47485(11) .0548(5) Uani d . 1 . . O N3 .64354(7) .2343(2) .51945(9) .0280(4) Uani d . 1 . . N N4 .43802(8) .2637(2) .51176(11) .0330(4) Uani d . 1 . . N C7 .55361(8) .2205(2) .39046(9) .0213(4) Uani d . 1 . . C C8 .57792(7) .2348(2) .47266(9) .0185(4) Uani d . 1 . . C C9 .53986(8) .2490(2) .51128(10) .0203(4) Uani d . 1 . . C C10 .47674(8) .2462(2) .47097(10) .0221(4) Uani d . 1 . . C C11 .45001(9) .2236(3) .39123(11) .0276(4) Uani d . 1 . . C C12 .48719(9) .2099(3) .35305(11) .0266(4) Uani d . 1 . . C H9 .5566(9) .265(3) .5642(12) .032(5) Uiso d . 1 . . H H11 .4071(10) .211(3) .3667(11) .035(6) Uiso d . 1 . . H H12 .4715(9) .192(3) .2992(12) .029(5) Uiso d . 1 . . H N2 .70352(8) .8253(2) .29971(9) .0314(4) Uani d . 1 . . N N1 .65687(7) .5294(2) .34453(8) .0244(4) Uani d . 1 . . N C6 .72565(12) .6282(4) .28377(15) .0415(6) Uani d . 1 . . C C5 .69363(10) .4447(3) .30379(12) .0315(5) Uani d . 1 . . C C4 .72097(13) .8416(4) .38215(12) .0406(6) Uani d . 1 . . C C3 .69868(10) .6522(3) .41216(10) .0312(5) Uani d . 1 . . C C2 .63628(11) .8327(3) .26148(12) .0371(5) Uani d . 1 . . C C1 .60612(9) .6663(4) .29156(13) .0349(5) Uani d . 1 . . C H6A .7171(11) .618(4) .2322(14) .058(7) Uiso d . 1 . . H H6B .7754(15) .613(5) .3194(16) .097(10) Uiso d . 1 . . H H5A .6642(11) .375(4) .2609(13) .053(7) Uiso d . 1 . . H H5B .7264(11) .351(3) .3416(12) .045(6) Uiso d . 1 . . H H4A .7015(11) .976(4) .3895(13) .058(7) Uiso d . 1 . . H H4B .7636(16) .842(4) .4022(16) .083(10) Uiso d . 1 . . H H3A .6742(12) .690(3) .4419(14) .055(7) Uiso d . 1 . . H H3B .7320(12) .557(4) .4417(13) .063(7) Uiso d . 1 . . H H2A .6235(11) .983(4) .2713(12) .059(7) Uiso d . 1 . . H H2B .6267(11) .810(3) .2091(14) .053(7) Uiso d . 1 . . H H1A .5844(13) .719(4) .3250(15) .066(8) Uiso d . 1 . . H H1B .5785(11) .579(4) .2516(13) .057(7) Uiso d . 1 . . H H1N1 .6332(11) .416(4) .3555(12) .057(7) 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 .0347(8) .0383(8) .0304(7) -.0129(6) .0205(6) -.0063(6) O2 .0207(7) .0819(12) .0471(9) -.0017(7) .0163(7) .0097(8) O3 .0320(9) .1068(14) .0234(7) -.0008(9) .0005(6) .0050(8) O4 .0687(12) .0349(8) .0531(10) .0032(7) .0468(9) .0014(7) O5 .0323(9) .0557(10) .0895(13) .0058(8) .0385(9) .0000(8) N3 .0210(8) .0312(9) .0294(8) -.0012(7) .0080(7) .0027(6) N4 .0401(10) .0166(8) .0572(12) .0019(7) .0352(9) .0018(7) C7 .0269(9) .0148(8) .0240(9) -.0043(7) .0121(7) -.0007(6) C8 .0161(8) .0153(8) .0231(8) -.0002(6) .0071(7) .0015(6) C9 .0292(10) .0122(8) .0212(9) -.0004(7) .0122(7) .0011(6) C10 .0243(9) .0117(8) .0366(10) .0014(7) .0188(8) .0011(7) C11 .0177(9) .0237(9) .0372(10) -.0005(8) .0071(8) .0033(8) C12 .0270(10) .0267(10) .0228(9) -.0052(8) .0070(7) -.0003(7) N2 .0373(10) .0283(9) .0343(9) -.0004(7) .0206(8) .0063(7) N1 .0223(8) .0265(8) .0275(8) -.0028(7) .0134(6) .0017(6) C6 .0493(15) .0413(13) .0518(14) .0103(11) .0388(12) .0090(10) C5 .0307(11) .0269(10) .0392(11) .0036(9) .0168(9) -.0051(9) C4 .0446(14) .0381(13) .0344(11) -.0135(11) .0112(10) -.0016(9) C3 .0327(11) .0399(12) .0203(9) -.0037(9) .0103(8) -.0010(8) C2 .0434(13) .0372(12) .0296(11) .0110(10) .0138(9) .0085(9) C1 .0198(10) .0455(13) .0372(11) .0081(9) .0094(9) -.0005(10) 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 C7 . 1.270(2) ? O2 N3 . 1.223(2) ? O3 N3 . 1.227(2) ? O4 N4 . 1.236(2) ? O5 N4 . 1.234(2) ? N3 C8 . 1.441(2) ? N4 C10 . 1.434(2) ? C7 C12 . 1.438(3) ? C7 C8 . 1.442(2) ? C8 C9 . 1.385(2) ? C9 C10 . 1.373(3) ? C9 H9 . .93(2) ? C10 C11 . 1.402(3) ? C11 C12 . 1.360(3) ? C11 H11 . .93(2) ? C12 H12 . .950(19) ? N2 C6 . 1.455(3) ? N2 C2 . 1.456(3) ? N2 C4 . 1.465(3) ? N1 C5 . 1.492(2) ? N1 C3 . 1.496(2) ? N1 C1 . 1.502(2) ? N1 H1N1 . 1.00(3) ? C2 C1 . 1.528(3) yes C4 C3 . 1.534(3) yes C6 C5 . 1.538(3) yes C6 H6A . .93(2) ? C6 H6B . 1.10(3) ? C5 H5A . .95(2) ? C5 H5B . 1.02(2) ? C4 H4A . 1.02(3) ? C4 H4B . .92(3) ? C3 H3A . 1.00(3) ? C3 H3B . .98(3) ? C2 H2A . 1.06(2) ? C2 H2B . .95(2) ? C1 H1A . 1.03(3) ? C1 H1B . .96(2) ?