data_2012458 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2002 _journal_volume 58 _journal_page_first o6 _journal_page_last o8 _publ_section_title ; A structural hierarchy in the hydrogen-bonded adduct N,N'-dimethylpiperazine--tartaric acid--water (1/2/2): an N-component N-dimensional structure (N = 3) with substructures having N = 1 and 2 ; loop_ _publ_author_name 'Farrell, Dorcas M. M.' 'Ferguson, George' 'Lough, Alan J.' 'Glidewell, Christopher' _chemical_formula_moiety 'C6 H16 N2 2+, 2C4 H5 O6 1-, 2H2 O' _chemical_formula_sum 'C14 H30 N2 O14' _chemical_formula_iupac 'C6 H16 N2 2+, 2C4 H5 O6 1-, 2H2 O' _chemical_formula_weight 450.40 _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 7.2907(3) _cell_length_b 8.3423(4) _cell_length_c 8.4324(4) _cell_angle_alpha 96.406(2) _cell_angle_beta 106.359(2) _cell_angle_gamma 90.430(3) _cell_volume 488.63(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.531 _diffrn_ambient_temperature 150(12) 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 .32857(18) .40117(16) .41205(17) .0199(3) Uani d . 1 . . N C11 .3260(2) .5339(2) .5462(2) .0229(4) Uani d . 1 . . C C12 .5211(2) .5634(2) .6709(2) .0231(4) Uani d . 1 . . C C13 .1367(2) .3777(2) .2865(2) .0313(4) Uani d . 1 . . C O1 -.06654(15) .01311(13) .77621(14) .0204(3) Uani d . 1 . . O O2 -.02032(16) .27533(14) .87855(15) .0250(3) Uani d . 1 . . O O3 .59478(15) -.00246(14) .78062(14) .0207(3) Uani d . 1 . . O O4 .53434(15) .17035(13) .58960(14) .0200(3) Uani d . 1 . . O O5 .34509(15) .28538(14) .88812(15) .0259(3) Uani d . 1 . . O O6 .15410(15) .14631(13) .54491(13) .0207(3) Uani d . 1 . . O C1 .0353(2) .14454(19) .83062(19) .0178(3) Uani d . 1 . . C C2 .2476(2) .13263(19) .83847(19) .0183(3) Uani d . 1 . . C C3 .2709(2) .06235(19) .67021(19) .0171(3) Uani d . 1 . . C C4 .4815(2) .08143(18) .67629(19) .0172(3) Uani d . 1 . . C O7 .72788(18) .38219(16) 1.06172(17) .0308(3) Uani d . 1 . . O H1 .3574 .3061 .4602 .024 Uiso calc R 1 . . H H11A .2318 .5047 .6040 .027 Uiso calc R 1 . . H H11B .2856 .6342 .4958 .027 Uiso calc R 1 . . H H12A .5169 .6557 .7544 .028 Uiso calc R 1 . . H H12B .5552 .4670 .7301 .028 Uiso calc R 1 . . H H13A .1038 .4772 .2349 .047 Uiso calc R 1 . . H H13B .0404 .3514 .3415 .047 Uiso calc R 1 . . H H13C .1400 .2892 .2007 .047 Uiso calc R 1 . . H H3 .7076 .0115 .7768 .031 Uiso calc R 1 . . H H5 .2662 .3567 .8955 .039 Uiso calc R 1 . . H H6 .1245 .0864 .4538 .031 Uiso calc R 1 . . H H2 .3072 .0588 .9227 .022 Uiso calc R 1 . . H H3A .2305 -.0548 .6480 .021 Uiso calc R 1 . . H H71 .618(3) .338(3) 1.011(3) .042(6) Uiso d . 1 . . H H72 .803(4) .337(3) 1.004(3) .059(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 N1 .0183(6) .0208(7) .0194(7) -.0022(5) .0023(5) .0049(5) C11 .0217(8) .0240(8) .0253(9) .0008(7) .0105(7) .0031(7) C12 .0290(9) .0230(8) .0186(8) -.0015(7) .0091(7) .0025(7) C13 .0253(9) .0295(9) .0314(10) -.0039(7) -.0070(8) .0103(8) O1 .0152(5) .0226(6) .0241(6) .0000(4) .0071(5) .0025(5) O2 .0210(6) .0243(6) .0309(7) .0022(5) .0107(5) -.0002(5) O3 .0129(5) .0286(6) .0233(6) .0026(4) .0069(5) .0093(5) O4 .0184(5) .0205(6) .0234(6) .0000(4) .0085(5) .0055(5) O5 .0154(5) .0255(6) .0335(7) -.0026(5) .0065(5) -.0091(5) O6 .0179(5) .0257(6) .0166(6) .0009(5) .0021(5) .0023(5) C1 .0149(7) .0241(8) .0151(8) .0019(6) .0046(6) .0040(6) C2 .0143(7) .0224(8) .0176(8) -.0002(6) .0041(6) .0009(6) C3 .0151(7) .0191(7) .0178(8) .0004(6) .0050(6) .0038(6) C4 .0174(8) .0175(7) .0168(8) .0008(6) .0056(6) -.0003(6) O7 .0181(6) .0394(8) .0310(7) -.0009(6) .0055(6) -.0084(6) 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 C13 . 1.494(2) no N1 C11 . 1.496(2) no N1 C12 2_666 1.500(2) no N1 H1 . .93 no C11 C12 . 1.511(2) no C11 H11A . .99 no C11 H11B . .99 no C12 N1 2_666 1.500(2) no C12 H12A . .99 no C12 H12B . .99 no C13 H13A . .98 no C13 H13B . .98 no C13 H13C . .98 no O1 C1 . 1.2836(19) no O2 C1 . 1.2325(19) no O3 C4 . 1.2972(19) no O3 H3 . .84 no O4 C4 . 1.2281(18) no O5 C2 . 1.4155(18) no O5 H5 . .84 no O6 C3 . 1.4139(19) no O6 H6 . .84 no C1 C2 . 1.535(2) no C2 C3 . 1.529(2) no C2 H2 . 1.00 no C3 C4 . 1.528(2) no C3 H3A . 1.00 no O7 H71 . .86(2) no O7 H72 . .89(3) no