data_2012392 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1443 _journal_page_last 1446 _publ_section_title ; The 143 and 300 K polymorphs of hexamethylenetetraminium 2,4-dinitrophenolate monohydrate ; loop_ _publ_author_name 'Anwar Usman' 'Suchada Chantrapromma' 'Hoong-Kun Fun' _chemical_formula_moiety 'C6 H13 N4 1+, C6 H3 N2 O5 1-, H2 O' _chemical_formula_sum 'C12 H18 N6 O6' _chemical_formula_iupac 'C6 H13 N4 1+, C6 H3 N2 O5 1-, H2 O' _chemical_formula_weight 342.32 _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3877(4) _cell_length_b 7.9017(5) _cell_length_c 14.4042(9) _cell_angle_alpha 84.4120(10) _cell_angle_beta 86.3670(10) _cell_angle_gamma 89.3040(10) _cell_volume 722.11(8) _cell_formula_units_Z 2 _cell_measurement_temperature 143(2) _exptl_crystal_density_diffrn 1.574 _diffrn_ambient_temperature 143(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 N1 .2752(3) .6767(3) -.25439(15) .0154(5) Uani d . 1 . . N N2 .2440(3) .9482(3) .03112(14) .0147(5) Uani d . 1 . . N N3 .2238(3) .7463(3) .29237(15) .0133(5) Uani d . 1 . . N H1N3 .219(5) .733(4) .239(2) .025 Uiso d . 1 . . H N4 .4515(3) .8628(3) .39867(15) .0140(5) Uani d . 1 . . N N4A .0720(3) .9031(3) .41653(15) .0145(5) Uani d . 1 . . N N5 .2253(3) .6220(3) .45392(15) .0145(5) Uani d . 1 . . N O1 .2775(3) .5438(2) -.29495(13) .0222(5) Uani d . 1 . . O O2 .2812(3) .8190(3) -.29746(13) .0233(5) Uani d . 1 . . O O3 .2575(4) 1.0828(2) -.01981(14) .0272(5) Uani d . 1 . . O O4 .2269(4) .9473(3) .11750(14) .0288(6) Uani d . 1 . . O O5 .2311(3) .6037(2) .13357(12) .0178(5) Uani d . 1 . . O O1W -.2302(3) .7318(3) -.22082(14) .0242(5) Uani d . 1 . . O H1W1 -.234(5) .622(5) -.189(2) .028 Uiso d . 1 . . H H2W1 -.240(5) .796(5) -.175(2) .029 Uiso d . 1 . . H C1 .2629(4) .6592(3) -.15335(16) .0127(5) Uani d . 1 . . C C2 .2576(4) .8054(3) -.10769(18) .0140(6) Uani d . 1 . . C H2 .256(5) .919(5) -.140(2) .035(10) Uiso d . 1 . . H C3 .2473(4) .7898(3) -.01062(16) .0115(5) Uani d . 1 . . C C4 .2418(4) .6288(3) .04504(17) .0123(5) Uani d . 1 . . C C5 .2503(4) .4839(3) -.00912(18) .0156(6) Uani d . 1 . . C H5A .247(5) .373(4) .020(2) .022(8) Uiso d . 1 . . H C6 .2602(4) .4979(3) -.10400(18) .0136(5) Uani d . 1 . . C H6A .263(4) .404(4) -.139(2) .021(8) Uiso d . 1 . . H C7 .2059(4) .5831(3) .35838(18) .0156(6) Uani d . 1 . . C H7B .069(5) .532(4) .348(2) .020(8) Uiso d . 1 . . H H7A .322(5) .505(4) .334(2) .024 Uiso d . 1 . . H C8 .4297(4) .7033(3) .45981(19) .0162(6) Uani d . 1 . . C H8B .554(5) .625(4) .451(2) .022 Uiso d . 1 . . H H8A .438(5) .727(4) .519(2) .028(9) Uiso d . 1 . . H C8A .0584(4) .7438(3) .47820(18) .0152(6) Uani d . 1 . . C H8AB -.084(5) .689(4) .469(2) .022 Uiso d . 1 . . H H8AA .072(5) .767(4) .547(2) .027(8) Uiso d . 1 . . H C9 .4339(4) .8273(3) .30282(18) .0148(6) Uani d . 1 . . C H9B .448(5) .931(4) .259(2) .021(8) Uiso d . 1 . . H H9A .545(5) .749(4) .283(2) .028 Uiso d . 1 . . H C9A .0505(4) .8664(3) .32122(18) .0150(5) Uani d . 1 . . C H9AB .069(5) .961(4) .278(2) .024 Uiso d . 1 . . H H9AA -.084(5) .801(4) .314(2) .019(8) Uiso d . 1 . . H C10 .2787(4) .9795(3) .42406(18) .0149(6) Uani d . 1 . . C H10B .290(5) 1.087(4) .385(2) .029 Uiso d . 1 . . H H10A .279(4) 1.002(4) .486(2) .019(8) 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 .0139(11) .0187(11) .0140(11) .0035(9) -.0013(8) -.0036(9) N2 .0242(12) .0093(10) .0112(10) .0044(9) -.0043(8) -.0023(8) N3 .0184(12) .0132(11) .0091(10) .0033(8) -.0036(8) -.0040(9) N4 .0137(11) .0131(11) .0158(11) .0003(8) -.0034(8) -.0029(9) N4A .0141(11) .0139(11) .0162(11) .0024(8) -.0015(8) -.0045(9) N5 .0174(12) .0117(10) .0145(11) .0015(8) -.0016(8) -.0020(9) O1 .0297(12) .0217(11) .0172(10) .0072(8) -.0035(8) -.0115(8) O2 .0368(13) .0184(10) .0144(10) .0032(8) -.0017(8) .0000(8) O3 .0528(14) .0087(9) .0203(11) .0015(9) -.0044(9) -.0005(8) O4 .0617(16) .0135(10) .0122(9) .0042(9) -.0043(9) -.0053(8) O5 .0334(12) .0110(9) .0092(9) .0013(8) -.0029(7) -.0020(7) O1W .0399(13) .0158(10) .0165(10) .0018(9) -.0022(8) -.0001(9) C1 .0142(13) .0163(13) .0083(11) .0035(10) -.0020(9) -.0043(10) C2 .0152(13) .0122(12) .0148(12) .0024(10) -.0013(9) -.0021(10) C3 .0158(13) .0074(11) .0121(12) .0024(9) -.0043(9) -.0033(10) C4 .0137(12) .0099(12) .0144(12) .0022(9) -.0030(9) -.0050(10) C5 .0235(14) .0083(12) .0155(13) .0022(10) -.0022(9) -.0026(10) C6 .0156(13) .0120(12) .0142(12) .0026(9) -.0017(9) -.0055(10) C7 .0207(14) .0090(12) .0184(13) .0021(10) -.0052(10) -.0050(10) C8 .0170(14) .0162(13) .0155(12) .0003(10) -.0051(10) .0007(11) C8A .0165(13) .0146(13) .0145(12) .0020(10) -.0005(9) -.0025(10) C9 .0135(13) .0156(13) .0150(12) .0008(10) .0010(9) -.0018(11) C9A .0128(13) .0166(13) .0165(12) .0045(10) -.0035(9) -.0059(11) C10 .0180(14) .0136(13) .0141(12) .0017(10) -.0029(9) -.0057(11) 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 N1 O2 . 1.230(3) yes N1 O1 . 1.250(3) yes N1 C1 . 1.446(3) yes N2 O3 . 1.232(3) yes N2 O4 . 1.241(3) yes N2 C3 . 1.440(3) yes N3 C9A . 1.514(3) yes N3 C9 . 1.516(3) yes N3 C7 . 1.526(3) yes N3 H1N3 . .79(3) no N4 C9 . 1.447(3) yes N4 C8 . 1.469(3) yes N4 C10 . 1.480(3) yes N4A C9A . 1.446(3) yes N4A C8A . 1.468(3) yes N4A C10 . 1.473(3) yes N5 C7 . 1.452(3) yes N5 C8 . 1.473(3) yes N5 C8A . 1.476(3) yes O5 C4 . 1.269(3) yes O1W H1W1 . .94(3) no O1W H2W1 . .87(4) no C1 C2 . 1.383(3) no C1 C6 . 1.398(4) no C2 C3 . 1.389(3) no C2 H2 . .97(4) ? C3 C4 . 1.436(3) no C4 C5 . 1.446(3) no C5 C6 . 1.358(3) no C5 H5A . .93(3) ? C6 H6A . .94(3) ? C7 H7B . 1.00(3) ? C7 H7A . 1.03(3) ? C8 H8B . 1.01(3) ? C8 H8A . .90(3) ? C8A H8AB . 1.03(3) ? C8A H8AA . 1.03(3) ? C9 H9B . .99(3) ? C9 H9A . .98(3) ? C9A H9AB . .93(3) ? C9A H9AA . 1.03(3) ? C10 H10B . .97(3) ? C10 H10A . .92(3) ?