data_2011324 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 1126 _journal_page_last 1128 _publ_section_title ; Three-fold interweaving of (4,4) nets built from R~10~^10^(58) rings in the hydrogen-bonded adduct 1,4-diazabicyclo[2.2.2]octane--5-hydroxyisophthalic acid (1/1). ; loop_ _publ_author_name 'Burchell, Colin J.' 'Ferguson, George' 'Lough, Alan J.' 'Glidewell, Christopher' _chemical_formula_moiety 'C6 H13 N2 + , C8 H5 O5 -' _chemical_formula_sum 'C14 H18 N2 O5' _chemical_formula_iupac 'C6 H13 N2 + , C8 H5 O5 -' _chemical_formula_weight 294.30 _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 17.3820(7) _cell_length_b 6.7257(3) _cell_length_c 23.9374(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.368(2) _cell_angle_gamma 90.00 _cell_volume 2786.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _exptl_crystal_density_diffrn 1.403 _diffrn_ambient_temperature 100(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 .39457(9) .05729(19) .26981(5) .0418(4) Uani d . 1 . . O O2 .40922(7) -.23375(17) .22730(4) .0275(3) Uani d . 1 . . O O3 .40066(7) -.25995(19) .01873(5) .0324(3) Uani d . 1 . . O O4 .32665(8) -.03613(19) -.02918(5) .0362(3) Uani d . 1 . . O O5 .28335(7) .49964(17) .11376(5) .0282(3) Uani d . 1 . . O C11 .37110(8) .0418(2) .17004(6) .0191(3) Uani d . 1 . . C C12 .37641(8) -.0701(2) .12141(6) .0191(3) Uani d . 1 . . C C13 .35333(8) .0129(2) .06887(6) .0188(3) Uani d . 1 . . C C14 .32246(8) .2052(2) .06578(6) .0197(3) Uani d . 1 . . C C15 .31530(8) .3148(2) .11451(6) .0198(3) Uani d . 1 . . C C16 .34178(8) .2345(2) .16651(6) .0202(3) Uani d . 1 . . C C17 .39303(9) -.0436(2) .22738(6) .0218(3) Uani d . 1 . . C C18 .35997(9) -.1036(2) .01545(6) .0229(4) Uani d . 1 . . C N1 .41700(7) -.39877(19) .32670(5) .0208(3) Uani d . 1 . . N N2 .40638(7) -.5779(2) .41892(5) .0210(3) Uani d . 1 . . N C1 .34314(9) -.5094(3) .32486(7) .0245(4) Uani d . 1 . . C C2 .48131(9) -.5425(2) .33731(7) .0234(4) Uani d . 1 . . C C3 .41909(10) -.2537(2) .37345(7) .0241(4) Uani d . 1 . . C C4 .33853(10) -.6288(3) .37880(7) .0343(4) Uani d . 1 . . C C5 .47902(11) -.6391(3) .39542(8) .0412(5) Uani d . 1 . . C C6 .40781(13) -.3597(3) .42890(7) .0366(5) Uani d . 1 . . C H2 .4137 -.2765 .2604 .041 Uiso calc R 1 . . H H5 .2565 .5173 .0831 .042 Uiso calc R 1 . . H H12 .3956 -.2024 .1240 .023 Uiso calc R 1 . . H H14 .3062 .2615 .0302 .024 Uiso calc R 1 . . H H16 .3398 .3116 .1996 .024 Uiso calc R 1 . . H H2A .4024 -.6438 .4527 .025 Uiso calc R 1 . . H H1A .3390 -.6006 .2923 .029 Uiso calc R 1 . . H H1B .2994 -.4146 .3201 .029 Uiso calc R 1 . . H H2B .5312 -.4730 .3355 .028 Uiso calc R 1 . . H H2C .4770 -.6467 .3080 .028 Uiso calc R 1 . . H H3A .3777 -.1537 .3654 .029 Uiso calc R 1 . . H H3B .4694 -.1834 .3768 .029 Uiso calc R 1 . . H H4A .2901 -.5965 .3955 .041 Uiso calc R 1 . . H H4B .3386 -.7729 .3704 .041 Uiso calc R 1 . . H H5A .4808 -.7857 .3920 .049 Uiso calc R 1 . . H H5B .5243 -.5957 .4207 .049 Uiso calc R 1 . . H H6A .4506 -.3254 .4575 .044 Uiso calc R 1 . . H H6B .3587 -.3166 .4429 .044 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 O1 .0797(10) .0264(7) .0181(6) .0110(7) -.0025(6) -.0019(5) O2 .0444(7) .0218(6) .0163(6) .0078(5) .0026(5) .0030(5) O3 .0471(7) .0300(7) .0200(6) .0158(6) .0016(5) -.0029(5) O4 .0536(8) .0328(7) .0200(6) .0125(6) -.0087(5) -.0037(5) O5 .0394(7) .0198(6) .0241(6) .0083(5) -.0033(5) -.0016(5) C11 .0181(7) .0217(8) .0172(8) -.0006(6) .0008(6) .0017(6) C12 .0187(7) .0187(7) .0201(8) .0019(6) .0020(6) .0011(6) C13 .0178(7) .0209(8) .0180(8) .0002(6) .0023(6) -.0004(6) C14 .0201(7) .0210(8) .0174(8) -.0003(6) -.0006(6) .0032(6) C15 .0207(7) .0166(7) .0220(8) .0011(6) .0011(6) .0000(6) C16 .0225(7) .0199(8) .0180(8) -.0007(6) .0018(6) -.0021(6) C17 .0267(8) .0214(8) .0174(8) .0022(7) .0019(6) .0005(6) C18 .0278(8) .0225(8) .0181(8) .0021(7) .0010(6) -.0009(6) N1 .0240(6) .0179(7) .0207(7) .0021(5) .0036(5) .0021(5) N2 .0249(6) .0205(7) .0179(7) -.0018(5) .0034(5) .0037(5) C1 .0235(8) .0276(9) .0219(8) .0004(7) -.0009(6) .0001(7) C2 .0235(7) .0230(8) .0244(9) .0033(7) .0061(6) .0025(7) C3 .0325(8) .0170(8) .0232(8) .0005(7) .0044(7) -.0002(6) C4 .0304(9) .0463(12) .0256(9) -.0147(9) -.0001(7) .0040(8) C5 .0360(10) .0475(12) .0427(12) .0205(9) .0172(8) .0245(10) C6 .0644(13) .0220(9) .0229(9) -.0040(9) .0006(8) -.0016(7) 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 C17 . 1.220(2) y O2 C17 . 1.310(2) y O2 H2 . .84 no O3 C18 . 1.2654(19) y O4 C18 . 1.2518(19) y O5 C15 . 1.3609(18) y O5 H5 . .84 no C11 C16 . 1.393(2) no C11 C12 . 1.397(2) no C11 C17 . 1.504(2) y C12 C13 . 1.400(2) no C12 H12 . .95 no C13 C14 . 1.399(2) no C13 C18 . 1.513(2) y C14 C15 . 1.396(2) no C14 H14 . .95 no C15 C16 . 1.395(2) no C16 H16 . .95 no N1 C1 . 1.481(2) y N1 C2 . 1.482(2) y N1 C3 . 1.483(2) y N2 C6 . 1.487(2) y N2 C5 . 1.487(2) y N2 C4 . 1.489(2) y N2 H2A . .93 no C1 C4 . 1.529(2) no C1 H1A . .99 no C1 H1B . .99 no C2 C5 . 1.539(2) no C2 H2B . .99 no C2 H2C . .99 no C3 C6 . 1.535(2) no C3 H3A . .99 no C3 H3B . .99 no C4 H4A . .99 no C4 H4B . .99 no C5 H5A . .99 no C5 H5B . .99 no C6 H6A . .99 no C6 H6B . .99 no