data_2012977
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o600
_journal_page_last  o601
_publ_section_title
;
The 2:1 complex of maleic acid and 1,4-diazabicyclo[2.2.2]octane:
hydrogen-bonded sheets linked by C-H...O hydrogen bonds
;
loop_
_publ_author_name
  'Cui, Rong Sun'
  'Zhi, Min Jin'
_chemical_formula_moiety  'C6 H14 N2 2+ , 2C4 H3 O4 -'
_chemical_formula_sum  'C14 H20 N2 O8'
_chemical_formula_weight  344.32
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'C m c 21'
_symmetry_space_group_name_Hall  'C 2c -2'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, z+1/2'
  'x, -y, z+1/2'
  '-x, y, z'
  'x+1/2, y+1/2, z'
  '-x+1/2, -y+1/2, z+1/2'
  'x+1/2, -y+1/2, z+1/2'
  '-x+1/2, y+1/2, z'
_cell_length_a  6.7584(8)
_cell_length_b  20.145(4)
_cell_length_c  11.255(2)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1532.3(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  289(2)
_exptl_crystal_density_diffrn  1.493
_diffrn_ambient_temperature  289(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 -0.026(4) 0.57705(14) 0.2955(2) 0.038(4) Uani d P 0.50 . . O
  O2 0.0000 0.65294(10) 0.4369(2) 0.0436(7) Uani d S 1 . . O
  O3 0.029(4) 0.45539(14) 0.2817(2) 0.047(5) Uani d P 0.50 . . O
  H3 0.0476 0.4955 0.2869 0.056 Uiso calc PR 0.50 . . H
  O4 0.0000 0.37082(10) 0.4034(3) 0.0480(7) Uani d S 1 . . O
  O5 0.0000 0.83938(10) -0.2111(2) 0.0423(7) Uani d S 1 . . O
  O6 0.0000 0.91495(11) -0.0687(2) 0.0472(7) Uani d S 1 . . O
  O7 0.0000 0.83663(12) -0.4278(2) 0.0456(7) Uani d S 1 . . O
  H7 0.0226 0.8365 -0.3563 0.055 Uiso calc PR 0.50 . . H
  O8 0.0000 0.91015(13) -0.5729(2) 0.0578(8) Uani d S 1 . . O
  N1 0.0000 0.74108(11) 0.2607(2) 0.0299(6) Uani d SD 1 . . N
  H1 -0.0096 0.7107 0.3203 0.036 Uiso calc PR 0.50 . . H
  N2 0.0000 0.82516(13) 0.0990(2) 0.0362(7) Uani d SD 1 . . N
  H2 0.0096 0.8555 0.0394 0.043 Uiso calc PR 0.50 . . H
  C1 -0.019(5) 0.70581(17) 0.1439(3) 0.028(3) Uani d PD 0.50 . . C
  H1A -0.1343 0.6770 0.1447 0.034 Uiso calc PR 0.50 . . H
  H1B 0.0970 0.6789 0.1292 0.034 Uiso calc PR 0.50 . . H
  C2 -0.0412(12) 0.75845(15) 0.0467(3) 0.038(3) Uani d PD 0.50 . . C
  H2A 0.0510 0.7495 -0.0174 0.045 Uiso calc PR 0.50 . . H
  H2B -0.1743 0.7574 0.0145 0.045 Uiso calc PR 0.50 . . H
  C3 0.180(2) 0.7825(9) 0.2808(15) 0.035(3) Uani d PD 0.50 . . C
  H3A 0.2978 0.7552 0.2871 0.042 Uiso calc PR 0.50 . . H
  H3B 0.1673 0.8093 0.3520 0.042 Uiso calc PR 0.50 . . H
  C4 0.1862(16) 0.8258(5) 0.1694(14) 0.046(3) Uani d PD 0.50 . . C
  H4A 0.2148 0.8711 0.1928 0.056 Uiso calc PR 0.50 . . H
  H4B 0.2938 0.8108 0.1191 0.056 Uiso calc PR 0.50 . . H
  C5 -0.1777(15) 0.7850(7) 0.2641(15) 0.031(3) Uani d PD 0.50 . . C
  H5A -0.1925 0.8025 0.3440 0.037 Uiso calc PR 0.50 . . H
  H5B -0.2941 0.7586 0.2467 0.037 Uiso calc PR 0.50 . . H
  C6 -0.1693(17) 0.8431(4) 0.1770(13) 0.038(2) Uani d PD 0.50 . . C
  H6A -0.2911 0.8467 0.1318 0.046 Uiso calc PR 0.50 . . H
  H6B -0.1452 0.8847 0.2180 0.046 Uiso calc PR 0.50 . . H
  C7 0.0000 0.59369(14) 0.4019(3) 0.0318(7) Uani d S 1 . . C
  C8 0.021(6) 0.54210(18) 0.4978(3) 0.029(4) Uani d P 0.50 . . C
  H8 0.0405 0.5590 0.5738 0.035 Uiso calc PR 0.50 . . H
  C9 0.015(11) 0.47632(17) 0.4915(4) 0.031(6) Uani d P 0.50 . . C
  H9 0.0222 0.4551 0.5647 0.038 Uiso calc PR 0.50 . . H
  C10 0.0000 0.43055(15) 0.3884(3) 0.0346(8) Uani d S 1 . . C
  C11 0.0000 0.89922(16) -0.1748(3) 0.0321(7) Uani d S 1 . . C
  C12 0.0000 0.95505(15) -0.2623(3) 0.0390(9) Uani d S 1 . . C
  H12 0.0000 0.9972 -0.2286 0.047 Uiso calc SR 1 . . H
  C13 0.0000 0.95418(15) -0.3805(3) 0.0364(9) Uani d S 1 . . C
  H13 0.0000 0.9961 -0.4153 0.044 Uiso calc SR 1 . . H
  C14 0.0000 0.89827(17) -0.4673(3) 0.0355(9) Uani d S 1 . . C
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 0.057(13) 0.0325(12) 0.0252(12) -0.001(2) -0.003(2) 0.0040(10)
  O2 0.0756(19) 0.0237(10) 0.0315(12) 0.000 0.000 0.0030(11)
  O3 0.081(15) 0.0306(12) 0.0290(13) 0.006(3) 0.002(3) -0.0020(11)
  O4 0.0658(19) 0.0254(11) 0.0529(17) 0.000 0.000 -0.0012(12)
  O5 0.0673(18) 0.0219(11) 0.0375(14) 0.000 0.000 0.0033(11)
  O6 0.0829(19) 0.0311(11) 0.0275(12) 0.000 0.000 0.0063(11)
  O7 0.068(2) 0.0326(13) 0.0361(14) 0.000 0.000 -0.0066(11)
  O8 0.095(2) 0.0505(15) 0.0277(13) 0.000 0.000 -0.0039(13)
  N1 0.0473(16) 0.0220(11) 0.0204(12) 0.000 0.000 0.0047(10)
  N2 0.061(2) 0.0268(13) 0.0207(12) 0.000 0.000 0.0051(10)
  C1 0.035(9) 0.0264(15) 0.0242(15) 0.004(3) -0.005(3) -0.0048(12)
  C2 0.057(8) 0.0296(19) 0.0264(18) -0.001(2) -0.002(2) -0.0037(15)
  C3 0.042(7) 0.034(6) 0.027(5) -0.006(4) -0.006(3) 0.011(3)
  C4 0.045(4) 0.023(5) 0.071(5) -0.009(3) 0.002(4) 0.011(4)
  C5 0.034(6) 0.033(6) 0.027(5) -0.010(4) 0.011(4) -0.010(4)
  C6 0.053(5) 0.015(4) 0.046(3) 0.009(3) 0.003(4) 0.007(3)
  C7 0.045(2) 0.0239(14) 0.0265(17) 0.000 0.000 0.0037(13)
  C8 0.038(14) 0.0313(16) 0.0184(15) 0.001(3) -0.001(3) 0.0012(13)
  C9 0.040(17) 0.0301(16) 0.0242(15) 0.006(6) 0.000(4) 0.0045(15)
  C10 0.040(2) 0.0285(15) 0.0351(18) 0.000 0.000 -0.0019(13)
  C11 0.0395(19) 0.0280(16) 0.0288(17) 0.000 0.000 0.0051(14)
  C12 0.063(3) 0.0209(15) 0.0328(17) 0.000 0.000 -0.0022(15)
  C13 0.058(2) 0.0239(17) 0.0276(17) 0.000 0.000 0.0007(15)
  C14 0.040(2) 0.0353(18) 0.0310(19) 0.000 0.000 -0.0029(14)
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 . 1.257(6) yes
  O2 C7 . 1.257(4) yes
  O3 C10 . 1.315(6) yes
  O3 H3 . 0.8200 ?
  O4 C10 . 1.215(4) yes
  O5 C11 . 1.273(4) yes
  O6 C11 . 1.235(4) yes
  O7 C14 . 1.319(4) yes
  O7 H7 . 0.8200 ?
  O8 C14 . 1.212(4) yes
  N1 C5 . 1.493(4) yes
  N1 C3 . 1.493(4) yes
  N1 C1 . 1.500(3) yes
  N1 H1 . 0.9100 ?
  N2 C6 . 1.486(4) yes
  N2 C4 . 1.487(4) yes
  N2 C2 . 1.494(3) yes
  N2 H2 . 0.9100 ?
  C1 C2 . 1.531(4) ?
  C1 H1A . 0.9700 ?
  C1 H1B . 0.9700 ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 C4 . 1.528(4) ?
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?
  C5 C6 . 1.528(4) ?
  C5 H5A . 0.9700 ?
  C5 H5B . 0.9700 ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  C7 C8 . 1.505(6) ?
  C8 C9 . 1.328(5) ?
  C8 H8 . 0.9300 ?
  C9 C10 . 1.486(7) ?
  C9 H9 . 0.9300 ?
  C10 O4 4 1.215(4) ?
  C10 O3 4 1.315(6) ?
  C10 C9 4 1.486(7) ?
  C11 O6 4 1.235(4) ?
  C11 O5 4 1.273(4) ?
  C11 C12 4 1.495(5) ?
  C11 C12 . 1.495(5) ?
  C12 C13 . 1.331(4) ?
  C12 H12 . 0.9300 ?
  C13 C14 . 1.491(5) ?
  C13 H13 . 0.9300 ?
  C14 O8 4 1.212(4) ?
  C14 O7 4 1.319(4) ?
  C14 C13 4 1.491(5) ?