data_2200056
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o22
_journal_page_last  o23
_publ_section_title
;
2,2'-Iminobis(ethylammonium) phthalate
;
loop_
_publ_author_name
  'Edwards, Selvin H.'
  'Kahwa, Ishenkumba A.'
  'Mague, Joel T.'
_chemical_formula_moiety  'C4 H15 N3 1+, C8 H4 O4 1-'
_chemical_formula_sum  'C12 H19 N3 O4'
_chemical_formula_iupac  'C4 H15 N3 1+, C8 H4 O4 1-'
_chemical_formula_weight  269.30
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  11.7634(8)
_cell_length_b  11.0250(10)
_cell_length_c  12.0322(7)
_cell_angle_alpha  90.00
_cell_angle_beta  115.3780(10)
_cell_angle_gamma  90.00
_cell_volume  1409.0(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.269
_diffrn_ambient_temperature  293(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  .76079(18)  .0159(2)  .47152(17)  .0662(6) Uani d . 1 . . O
  O2  .92677(15)  .11559(16)  .60395(15)  .0451(5) Uani d . 1 . . O
  O3 1.01283(15)  .21397(15)  .88155(16)  .0437(5) Uani d . 1 . . O
  O4 1.01029(15)  .01335(15)  .86180(16)  .0456(5) Uani d . 1 . . O
  C1  .7505(2)  .09581(19)  .6492(2)  .0328(6) Uani d . 1 . . C
  C2  .8158(2)  .1178(2)  .7749(2)  .0341(6) Uani d . 1 . . C
  C3  .7493(2)  .1416(2)  .8438(2)  .0459(7) Uani d . 1 . . C
  H3  .7928  .1569  .9276  .055 Uiso calc R 1 . . H
  C4  .6202(3)  .1429(3)  .7900(3)  .0608(8) Uani d . 1 . . C
  H4  .5767  .1592  .8371  .073 Uiso calc R 1 . . H
  C5  .5551(2)  .1200(3)  .6655(3)  .0580(8) Uani d . 1 . . C
  H5  .4676  .1196  .6288  .070 Uiso calc R 1 . . H
  C6  .6201(2)  .0981(2)  .5968(3)  .0463(7) Uani d . 1 . . C
  H6  .5758  .0843  .5128  .056 Uiso calc R 1 . . H
  C7  .8184(2)  .0747(2)  .5689(2)  .0364(6) Uani d . 1 . . C
  C8  .9574(2)  .1144(2)  .8416(2)  .0356(6) Uani d . 1 . . C
  N1 1.1283(2)  -.0689(2)  .6832(2)  .0387(5) Uani d . 1 . . N
  H1A 1.161(2)  -.052(2)  .619(2)  .054(8) Uiso d . 1 . . H
  H1B 1.080(3)  -.141(3)  .658(3)  .082(10) Uiso d . 1 . . H
  H1C 1.070(3)  -.008(3)  .682(3)  .062(9) Uiso d . 1 . . H
  N2 1.2352(2)  .13870(19)  .8313(2)  .0417(5) Uani d . 1 . . N
  H2 1.197(2)  .133(2)  .876(2)  .041(8) Uiso d . 1 . . H
  N3 1.1116(2)  .3008(2)  .6339(2)  .0447(6) Uani d . 1 . . N
  H3A 1.084(3)  .293(3)  .541(3)  .088(11) Uiso d . 1 . . H
  H3B 1.076(2)  .375(3)  .646(2)  .056(8) Uiso d . 1 . . H
  H3C 1.080(3)  .248(3)  .660(3)  .060(10) Uiso d . 1 . . H
  C9 1.2363(2)  -.0796(2)  .8049(2)  .0448(7) Uani d . 1 . . C
  H9A 1.2892  -.1468  .8042  .054 Uiso calc R 1 . . H
  H9B 1.2062  -.0960  .8668  .054 Uiso calc R 1 . . H
  C10 1.3128(2)  .0368(2)  .8368(3)  .0474(7) Uani d . 1 . . C
  H10A 1.3805  .0302  .9190  .057 Uiso calc R 1 . . H
  H10B 1.3500  .0487  .7796  .057 Uiso calc R 1 . . H
  C11 1.2859(2)  .2580(2)  .8323(2)  .0482(7) Uani d . 1 . . C
  H11A 1.3768  .2565  .8775  .058 Uiso calc R 1 . . H
  H11B 1.2526  .3150  .8722  .058 Uiso calc R 1 . . H
  C12 1.2497(2)  .2966(2)  .7014(2)  .0481(7) Uani d . 1 . . C
  H12A 1.2846  .3761  .7003  .058 Uiso calc R 1 . . H
  H12B 1.2836  .2397  .6619  .058 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  .0649(13)  .0957(16)  .0474(12)  -.0321(12)  .0330(11)  -.0286(11)
  O2  .0376(10)  .0561(12)  .0455(11)  -.0098(9)  .0215(8)  -.0025(8)
  O3  .0404(10)  .0368(10)  .0506(11)  -.0058(8)  .0164(8)  -.0120(8)
  O4  .0448(10)  .0358(10)  .0553(12)  .0039(8)  .0206(9)  .0063(8)
  C1  .0344(13)  .0253(12)  .0398(14)  -.0013(10)  .0170(11)  .0000(10)
  C2  .0377(13)  .0256(12)  .0434(14)  -.0029(10)  .0217(12)  -.0019(10)
  C3  .0476(16)  .0524(16)  .0444(15)  -.0048(13)  .0262(13)  -.0074(13)
  C4  .0528(18)  .072(2)  .075(2)  -.0050(15)  .0432(17)  -.0130(17)
  C5  .0330(14)  .069(2)  .076(2)  -.0065(14)  .0273(15)  -.0094(17)
  C6  .0382(15)  .0489(16)  .0477(15)  -.0059(12)  .0146(13)  -.0079(12)
  C7  .0388(14)  .0356(13)  .0360(14)  -.0020(11)  .0172(12)  .0029(11)
  C8  .0456(14)  .0332(14)  .0317(13)  -.0011(12)  .0199(11)  .0000(11)
  N1  .0436(12)  .0331(12)  .0424(13)  -.0008(11)  .0213(11)  -.0015(10)
  N2  .0414(12)  .0412(13)  .0449(13)  .0002(10)  .0207(11)  -.0035(10)
  N3  .0459(14)  .0329(13)  .0515(16)  .0001(11)  .0174(12)  .0025(11)
  C9  .0491(15)  .0377(14)  .0463(16)  .0053(12)  .0193(13)  .0045(11)
  C10  .0389(14)  .0461(16)  .0476(16)  .0052(12)  .0093(13)  .0007(12)
  C11  .0416(15)  .0392(15)  .0536(18)  -.0031(12)  .0106(13)  -.0107(12)
  C12  .0414(15)  .0402(15)  .0636(19)  .0007(12)  .0233(14)  .0007(13)
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 . 1.253(3) ?
  O2 C7 . 1.243(3) ?
  O3 C8 . 1.262(3) ?
  O4 C8 . 1.248(3) ?
  C1 C6 . 1.386(3) ?
  C1 C2 . 1.393(3) ?
  C1 C7 . 1.512(3) ?
  C2 C3 . 1.387(3) ?
  C2 C8 . 1.509(3) ?
  C3 C4 . 1.371(4) ?
  C4 C5 . 1.382(4) ?
  C5 C6 . 1.368(4) ?
  N1 C9 . 1.476(3) ?
  N2 C10 . 1.431(3) ?
  N2 C11 . 1.442(3) ?
  N3 C12 . 1.473(3) ?
  C9 C10 . 1.519(4) ?
  C11 C12 . 1.506(4) ?