data_2012603
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o129
_journal_page_last  o130
_publ_section_title
;
The binary adduct of 3,6,9,16,19,22-hexaazatricyclo[22.2.2.2^11,14^]triaconta-
11,13,24,26(1),27,29-hexaene and benzene-1,2,4,5-tetracarboxylic acid
;
loop_
_publ_author_name
  'Zhu, Long-Gen'
  'Ellern, Arkady M.'
  "Kosti\'c, Nenad M."
_chemical_formula_moiety  'C24 H42 N6 4+ , C10 H2 O8 4- , 6H2 O'
_chemical_formula_sum  'C34 H56 N6 O14'
_chemical_formula_weight  772.85
_symmetry_cell_setting  Triclinic
_symmetry_space_group_name_H-M  'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  7.0983(11)
_cell_length_b  9.3947(15)
_cell_length_c  13.880(2)
_cell_angle_alpha  87.686(3)
_cell_angle_beta  79.635(3)
_cell_angle_gamma  79.498(3)
_cell_volume  895.2(2)
_cell_formula_units_Z  1
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.434
_diffrn_ambient_temperature  298(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
  C1  .8509(4)  .7251(3)  -.0640(2)  .0211(7) Uani d . 1 . . C
  H1A  .8891  .6357  -.0947  .025 Uiso calc R 1 . . H
  C2  .8155(4)  .7308(3)  .0367(2)  .0226(8) Uani d . 1 . . C
  H2A  .8290  .6453  .0729  .027 Uiso calc R 1 . . H
  C3  .7603(4)  .8614(3)  .0846(2)  .0216(7) Uani d . 1 . . C
  C4  .7382(5)  .9867(3)  .0290(2)  .0310(9) Uani d . 1 . . C
  H4A  .6995 1.0758  .0600  .037 Uiso calc R 1 . . H
  C5  .7725(5)  .9816(3)  -.0711(2)  .0310(9) Uani d . 1 . . C
  H5A  .7568 1.0674  -.1069  .037 Uiso calc R 1 . . H
  C6  .8305(4)  .8501(3)  -.1204(2)  .0201(7) Uani d . 1 . . C
  C7  .8718(4)  .8484(3)  -.2298(2)  .0245(8) Uani d . 1 . . C
  H7A  .7508  .8773  -.2543  .029 Uiso calc R 1 . . H
  H7B  .9551  .9182  -.2535  .029 Uiso calc R 1 . . H
  C8 1.0187(4)  .6984(3)  -.3769(2)  .0248(8) Uani d . 1 . . C
  H8A 1.0968  .7715  -.4001  .030 Uiso calc R 1 . . H
  H8B  .9005  .7196  -.4047  .030 Uiso calc R 1 . . H
  C9  .7303(5)  .8729(3)  .1941(2)  .0256(8) Uani d . 1 . . C
  H9A  .8492  .8903  .2129  .031 Uiso calc R 1 . . H
  H9B  .6287  .9552  .2151  .031 Uiso calc R 1 . . H
  C10  .6379(4)  .7524(3)  .35371(19)  .0245(8) Uani d . 1 . . C
  H10A  .5416  .8380  .3738  .029 Uiso calc R 1 . . H
  H10B  .7569  .7612  .3762  .029 Uiso calc R 1 . . H
  C11  .5646(4)  .6183(3)  .3985(2)  .0228(8) Uani d . 1 . . C
  H11B  .5504  .6213  .4693  .027 Uiso calc R 1 . . H
  H11C  .4380  .6159  .3822  .027 Uiso calc R 1 . . H
  C12  .8703(4)  .4480(3)  .4100(2)  .0246(8) Uani d . 1 . . C
  H12B  .8277  .4467  .4804  .030 Uiso calc R 1 . . H
  H12C  .9545  .5194  .3946  .030 Uiso calc R 1 . . H
  C13  .3519(4)  .6153(3)  -.0037(2)  .0168(7) Uani d . 1 . . C
  C14  .3762(4)  .5523(3)  .0870(2)  .0162(7) Uani d . 1 . . C
  C15  .2411(4)  .6218(3)  .1773(2)  .0174(7) Uani d . 1 . . C
  C16  .5260(4)  .4341(3)  .09131(19)  .0164(7) Uani d . 1 . . C
  C17  .5522(5)  .3541(3)  .1858(2)  .0191(7) Uani d . 1 . . C
  H13  .249(4)  .691(3)  -.0032(16)  .015(8) Uiso d . 1 . . H
  H31N  .893(5)  .640(3)  -.246(2)  .050(12) Uiso d . 1 . . H
  H32N 1.103(7)  .669(5)  -.231(3)  .123(17) Uiso d . 1 . . H
  H21N  .628(4)  .408(3)  .3642(19)  .033(9) Uiso d . 1 . . H
  H11N  .566(5)  .714(3)  .223(2)  .035(10) Uiso d . 1 . . H
  H12N  .793(5)  .659(3)  .226(2)  .060(11) Uiso d . 1 . . H
  H11W  .165(8)  .771(6)  .327(4)  .16(2) Uiso d . 1 . . H
  H12W  .138(5)  .862(3)  .415(2)  .021(11) Uiso d . 1 . . H
  H21W  .149(5)  .040(4)  .550(2)  .062(13) Uiso d . 1 . . H
  H22W  .308(6)  .049(4)  .473(3)  .076(15) Uiso d . 1 . . H
  H31W  .462(5)  .226(4)  .347(3)  .071(14) Uiso d . 1 . . H
  H32W  .573(5)  .125(4)  .404(2)  .042(12) Uiso d . 1 . . H
  N1  .6755(4)  .7405(3)  .24451(17)  .0196(6) Uani d . 1 . . N
  N2  .7009(4)  .4883(3)  .36169(17)  .0211(6) Uani d . 1 . . N
  N3  .9681(4)  .7029(3)  -.26820(18)  .0204(6) Uani d . 1 . . N
  O1  .0740(3)  .5913(2)  .19808(13)  .0225(5) Uani d . 1 . . O
  O2  .3060(3)  .7094(2)  .22321(14)  .0226(5) Uani d . 1 . . O
  O3  .4079(3)  .3672(2)  .25511(13)  .0233(5) Uani d . 1 . . O
  O4  .7130(3)  .2751(2)  .18966(13)  .0238(5) Uani d . 1 . . O
  O5  .0755(4)  .8297(3)  .38912(19)  .0371(7) Uani d . 1 . . O
  O6  .2412(4)  -.0139(2)  .51266(18)  .0292(6) Uani d . 1 . . O
  O7  .4589(4)  .1539(3)  .39240(19)  .0431(7) Uani d . 1 . . O
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
  C1  .0182(18)  .0184(17)  .0263(19)  -.0021(14)  -.0035(14)  -.0036(14)
  C2  .026(2)  .0186(17)  .0233(18)  -.0077(14)  -.0017(15)  .0041(14)
  C3  .0218(19)  .0231(17)  .0196(18)  -.0080(14)  .0013(15)  .0002(14)
  C4  .041(2)  .0190(18)  .029(2)  -.0023(15)  .0029(17)  -.0036(15)
  C5  .037(2)  .0197(18)  .032(2)  .0005(16)  -.0020(17)  .0071(15)
  C6  .0146(17)  .0219(17)  .0239(18)  -.0061(14)  -.0012(14)  .0007(14)
  C7  .0231(19)  .0201(17)  .0302(19)  -.0020(14)  -.0059(15)  -.0008(14)
  C8  .0248(19)  .0291(19)  .0202(18)  -.0053(15)  -.0032(15)  .0030(14)
  C9  .031(2)  .0225(17)  .0234(18)  -.0124(15)  .0010(16)  .0016(14)
  C10  .0220(19)  .0273(18)  .0220(18)  -.0028(15)  .0018(15)  -.0048(14)
  C11  .0182(18)  .0281(18)  .0202(17)  -.0041(14)  .0019(14)  -.0013(14)
  C12  .0227(19)  .0300(18)  .0220(17)  -.0084(15)  -.0026(15)  .0002(14)
  C13  .0101(17)  .0152(16)  .0243(18)  -.0025(14)  -.0009(14)  .0002(14)
  C14  .0148(17)  .0171(16)  .0194(17)  -.0104(13)  -.0026(13)  -.0019(13)
  C15  .0193(19)  .0165(16)  .0151(17)  -.0022(14)  -.0021(14)  .0050(13)
  C16  .0150(17)  .0177(16)  .0185(17)  -.0087(13)  -.0023(14)  -.0022(13)
  C17  .023(2)  .0164(16)  .0199(18)  -.0065(15)  -.0058(15)  .0003(13)
  N1  .0206(17)  .0220(15)  .0158(14)  -.0051(13)  -.0005(13)  -.0018(11)
  N2  .0207(16)  .0226(15)  .0201(14)  -.0055(12)  -.0020(12)  -.0017(12)
  N3  .0221(17)  .0194(15)  .0188(15)  -.0074(13)  .0019(13)  .0016(12)
  O1  .0170(12)  .0267(12)  .0230(12)  -.0067(10)  .0020(10)  -.0029(9)
  O2  .0222(13)  .0256(12)  .0203(12)  -.0077(10)  .0002(10)  -.0067(9)
  O3  .0174(12)  .0323(13)  .0178(12)  -.0049(10)  .0027(10)  .0055(9)
  O4  .0200(13)  .0268(12)  .0238(12)  .0007(10)  -.0068(10)  -.0005(9)
  O5  .0237(15)  .0521(17)  .0361(16)  -.0087(13)  -.0005(13)  -.0194(13)
  O6  .0238(15)  .0307(14)  .0323(15)  -.0050(12)  -.0018(12)  -.0058(12)
  O7  .0320(18)  .0575(19)  .0400(17)  -.0117(14)  -.0086(14)  .0251(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
  C1 C2 . 1.376(4) ?
  C1 C6 . 1.384(4) ?
  C1 H1A .  .9300 ?
  C2 C3 . 1.377(4) ?
  C2 H2A .  .9300 ?
  C3 C4 . 1.382(4) ?
  C3 C9 . 1.502(4) ?
  C4 C5 . 1.367(4) ?
  C4 H4A .  .9300 ?
  C5 C6 . 1.395(4) ?
  C5 H5A .  .9300 ?
  C6 C7 . 1.495(4) ?
  C7 N3 . 1.486(3) ?
  C7 H7A .  .9700 ?
  C7 H7B .  .9700 ?
  C8 N3 . 1.487(3) ?
  C8 C12 2_765 1.500(4) ?
  C8 H8A .  .9700 ?
  C8 H8B .  .9700 ?
  C9 N1 . 1.483(3) ?
  C9 H9A .  .9700 ?
  C9 H9B .  .9700 ?
  C10 N1 . 1.496(3) ?
  C10 C11 . 1.518(4) ?
  C10 H10A .  .9700 ?
  C10 H10B .  .9700 ?
  C11 N2 . 1.460(3) ?
  C11 H11B .  .9700 ?
  C11 H11C .  .9700 ?
  C12 N2 . 1.463(4) ?
  C12 C8 2_765 1.500(3) ?
  C12 H12B .  .9700 ?
  C12 H12C .  .9700 ?
  C13 C14 . 1.394(4) ?
  C13 C16 2_665 1.402(3) ?
  C13 H13 .  .92(2) ?
  C14 C16 . 1.398(4) ?
  C14 C15 . 1.524(4) ?
  C15 O1 . 1.251(3) ?
  C15 O2 . 1.258(3) ?
  C16 C13 2_665 1.402(3) ?
  C16 C17 . 1.509(4) ?
  C17 O4 . 1.252(3) ?
  C17 O3 . 1.265(3) ?
  N1 H11N .  .96(3) ?
  N1 H12N . 1.03(3) ?
  N2 H21N .  .99(3) ?
  N3 H31N .  .88(3) ?
  N3 H32N . 1.16(5) ?
  O5 H11W . 1.08(5) ?
  O5 H12W .  .73(3) ?
  O6 H21W .  .85(3) ?
  O6 H22W .  .92(4) ?
  O7 H31W .  .91(4) ?
  O7 H32W .  .84(3) ?