#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012910.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2012910
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o470
_journal_page_last  o473
_publ_section_title
;
The salt-type 1:2 adduct of
meso-5,5,7,12,12,14-hexa-C-methyl-1,4,8,11-tetraazacyclotetradecane (tet-a) and
5-nitroisophthalic acid forms a hydrogen-bonded sheet structure containing two
configurational isomers of [{(tet-a)H~2~}^2+^]
;
loop_
_publ_author_name
  'MacLean, Elizabeth J.'
  'Teat, Simon J.'
  'Farrell, Dorcas M. M.'
  'Ferguson, George'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C16 H38 N4 2+ , 2C8 H4 N O6 -'
_chemical_formula_sum  'C32 H46 N6 O12'
_chemical_formula_iupac  'C16 H38 N4 2+ , 2C8 H4 N O6 -'
_chemical_formula_weight  706.46
_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  8.5183(6)
_cell_length_b  10.2278(8)
_cell_length_c  11.3272(9)
_cell_angle_alpha  66.6350(10)
_cell_angle_beta  71.3870(10)
_cell_angle_gamma  82.9760(10)
_cell_volume  858.54(11)
_cell_formula_units_Z  1
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.367
_diffrn_ambient_temperature  150(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 1.49566(14) 1.15193(14) 0.06528(15) 0.0536(4) Uani d . 1 . . O
  O2 1.43084(14) 0.92631(13) 0.19819(14) 0.0480(3) Uani d . 1 . . O
  H2 1.5255 0.9253 0.2066 0.072 Uiso calc R 1 . . H
  O3 0.88430(14) 0.74429(12) 0.36103(14) 0.0471(3) Uani d . 1 . . O
  O4 0.68298(13) 0.86088(15) 0.27784(13) 0.0498(4) Uani d . 1 . . O
  O5 0.82203(17) 1.34823(17) -0.07586(17) 0.0701(5) Uani d . 1 . . O
  O6 1.06128(18) 1.44045(16) -0.13114(18) 0.0726(5) Uani d . 1 . . O
  N11 0.96118(17) 1.34182(16) -0.06684(15) 0.0457(4) Uani d . 1 . . N
  C11 1.22518(16) 1.06822(15) 0.11204(14) 0.0285(3) Uani d . 1 . . C
  C12 1.11236(16) 0.95671(15) 0.19031(14) 0.0280(3) Uani d . 1 . . C
  H12 1.1474 0.8693 0.2470 0.034 Uiso calc R 1 . . H
  C13 0.94868(15) 0.97090(15) 0.18704(13) 0.0270(3) Uani d . 1 . . C
  C14 0.89797(16) 1.09789(16) 0.10156(14) 0.0295(3) Uani d . 1 . . C
  H14 0.7877 1.1092 0.0964 0.035 Uiso calc R 1 . . H
  C15 1.01319(17) 1.20707(16) 0.02434(14) 0.0324(3) Uani d . 1 . . C
  C16 1.17551(18) 1.19641(17) 0.02789(15) 0.0339(3) Uani d . 1 . . C
  H16 1.2505 1.2742 -0.0255 0.041 Uiso calc R 1 . . H
  C17 1.39859(16) 1.05513(16) 0.12086(14) 0.0310(3) Uani d . 1 . . C
  C18 0.82911(17) 0.84889(16) 0.28138(15) 0.0317(3) Uani d . 1 . . C
  N1 0.63983(16) 0.33334(14) 0.49439(14) 0.0272(3) Uani d P 0.847(3) A -1 N
  H1 0.5780 0.2735 0.5778 0.033 Uiso calc PR 0.847(3) A -1 H
  C2 0.7882(2) 0.3796(2) 0.5081(2) 0.0323(4) Uani d P 0.847(3) A -1 C
  H2A 0.8469 0.4548 0.4221 0.039 Uiso calc PR 0.847(3) A -1 H
  H2B 0.8644 0.2981 0.5285 0.039 Uiso calc PR 0.847(3) A -1 H
  C3 0.7408(3) 0.4364(3) 0.6193(3) 0.0343(5) Uani d P 0.847(3) A -1 C
  H3A 0.6701 0.3662 0.7032 0.041 Uiso calc PR 0.847(3) A -1 H
  H3B 0.8415 0.4532 0.6371 0.041 Uiso calc PR 0.847(3) A -1 H
  N4 0.6482(6) 0.5736(3) 0.5761(4) 0.0274(5) Uani d P 0.847(3) A -1 N
  H4A 0.5603 0.5574 0.5530 0.033 Uiso calc PR 0.847(3) A -1 H
  H4B 0.7173 0.6386 0.5003 0.033 Uiso calc PR 0.847(3) A -1 H
  C5 0.5825(7) 0.6389(6) 0.6830(6) 0.0351(5) Uani d P 0.847(3) A -1 C
  C51 0.7283(6) 0.6911(5) 0.7042(6) 0.0502(11) Uani d P 0.847(3) A -1 C
  H51A 0.7967 0.6097 0.7400 0.075 Uiso calc PR 0.847(3) A -1 H
  H51B 0.6864 0.7385 0.7683 0.075 Uiso calc PR 0.847(3) A -1 H
  H51C 0.7953 0.7584 0.6180 0.075 Uiso calc PR 0.847(3) A -1 H
  C52 0.4772(10) 0.5286(8) 0.8141(7) 0.0572(10) Uani d P 0.847(3) A -1 C
  H52A 0.3984 0.4842 0.7941 0.086 Uiso calc PR 0.847(3) A -1 H
  H52B 0.4164 0.5757 0.8756 0.086 Uiso calc PR 0.847(3) A -1 H
  H52C 0.5494 0.4553 0.8564 0.086 Uiso calc PR 0.847(3) A -1 H
  C6 0.4813(7) 0.7698(6) 0.6221(7) 0.0363(7) Uani d P 0.847(3) A -1 C
  H6A 0.4514 0.8239 0.6817 0.044 Uiso calc PR 0.847(3) A -1 H
  H6B 0.5539 0.8319 0.5342 0.044 Uiso calc PR 0.847(3) A -1 H
  C7 0.3217(2) 0.7412(2) 0.6003(2) 0.0319(4) Uani d P 0.847(3) A -1 C
  H7 0.2483 0.6778 0.6888 0.038 Uiso calc PR 0.847(3) A -1 H
  C71 0.2295(7) 0.8821(5) 0.5497(7) 0.0509(7) Uani d P 0.847(3) A -1 C
  H71A 0.2235 0.9365 0.6054 0.076 Uiso calc PR 0.847(3) A -1 H
  H71B 0.1172 0.8614 0.5558 0.076 Uiso calc PR 0.847(3) A -1 H
  H71C 0.2892 0.9379 0.4558 0.076 Uiso calc PR 0.847(3) A -1 H
  N21 0.7072(9) 0.3868(8) 0.4004(8) 0.0267(12) Uiso d PD 0.153(3) A -2 N
  H21 0.7604 0.4127 0.3098 0.032 Uiso calc PR 0.153(3) A -2 H
  C22 0.8227(13) 0.4009(14) 0.4656(10) 0.0267(12) Uiso d PD 0.153(3) A -2 C
  H22A 0.8990 0.4814 0.4020 0.032 Uiso calc PR 0.153(3) A -2 H
  H22B 0.8900 0.3132 0.4858 0.032 Uiso calc PR 0.153(3) A -2 H
  C23 0.7419(19) 0.4253(16) 0.5923(13) 0.0267(12) Uiso d PD 0.153(3) A -2 C
  H23A 0.6626 0.3460 0.6523 0.032 Uiso calc PR 0.153(3) A -2 H
  H23B 0.8287 0.4162 0.6359 0.032 Uiso calc PR 0.153(3) A -2 H
  N24 0.653(4) 0.558(2) 0.590(3) 0.0267(12) Uiso d PD 0.153(3) A -2 N
  H24A 0.5611 0.5495 0.5673 0.032 Uiso calc PR 0.153(3) A -2 H
  H24B 0.7186 0.6252 0.5137 0.032 Uiso calc PR 0.153(3) A -2 H
  C25 0.588(3) 0.637(3) 0.680(3) 0.0267(12) Uiso d PD 0.153(3) A -2 C
  C251 0.743(3) 0.676(3) 0.698(2) 0.0267(12) Uiso d PD 0.153(3) A -2 C
  H25A 0.8128 0.7391 0.6103 0.040 Uiso calc PR 0.153(3) A -2 H
  H25B 0.8046 0.5892 0.7329 0.040 Uiso calc PR 0.153(3) A -2 H
  H25C 0.7117 0.7245 0.7608 0.040 Uiso calc PR 0.153(3) A -2 H
  C252 0.488(4) 0.531(3) 0.816(3) 0.0267(12) Uiso d PD 0.153(3) A -2 C
  H25D 0.3916 0.4980 0.8053 0.040 Uiso calc PR 0.153(3) A -2 H
  H25E 0.4497 0.5783 0.8803 0.040 Uiso calc PR 0.153(3) A -2 H
  H25F 0.5573 0.4498 0.8489 0.040 Uiso calc PR 0.153(3) A -2 H
  C26 0.474(3) 0.757(4) 0.626(3) 0.0267(12) Uiso d PD 0.153(3) A -2 C
  H26A 0.5462 0.8422 0.5691 0.032 Uiso calc PR 0.153(3) A -2 H
  H26B 0.4018 0.7769 0.7051 0.032 Uiso calc PR 0.153(3) A -2 H
  C27 0.3601(13) 0.7565(11) 0.5463(12) 0.0267(12) Uiso d PD 0.153(3) A -2 C
  H27 0.4277 0.7803 0.4502 0.032 Uiso calc PR 0.153(3) A -2 H
  C271 0.237(3) 0.8766(19) 0.554(2) 0.0267(12) Uiso d PD 0.153(3) A -2 C
  H27A 0.1599 0.8815 0.5040 0.040 Uiso calc PR 0.153(3) A -2 H
  H27B 0.2976 0.9672 0.5136 0.040 Uiso calc PR 0.153(3) A -2 H
  H27C 0.1759 0.8585 0.6480 0.040 Uiso calc PR 0.153(3) A -2 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 0.0252(5) 0.0473(7) 0.0685(9) -0.0083(5) -0.0163(5) 0.0023(6)
  O2 0.0282(5) 0.0441(6) 0.0650(8) -0.0030(5) -0.0277(5) -0.0023(6)
  O3 0.0287(5) 0.0345(6) 0.0630(8) -0.0038(4) -0.0223(5) 0.0047(5)
  O4 0.0235(5) 0.0593(8) 0.0489(7) -0.0071(5) -0.0185(5) 0.0055(6)
  O5 0.0368(7) 0.0593(9) 0.0804(11) -0.0013(6) -0.0315(7) 0.0193(8)
  O6 0.0457(8) 0.0516(8) 0.0812(11) -0.0108(6) -0.0244(7) 0.0222(8)
  N11 0.0311(6) 0.0428(8) 0.0434(8) 0.0015(6) -0.0137(6) 0.0051(6)
  C11 0.0203(6) 0.0361(7) 0.0282(6) 0.0010(5) -0.0089(5) -0.0104(5)
  C12 0.0214(6) 0.0314(6) 0.0306(6) 0.0026(5) -0.0111(5) -0.0093(5)
  C13 0.0205(6) 0.0314(6) 0.0281(6) 0.0007(5) -0.0090(5) -0.0089(5)
  C14 0.0211(6) 0.0367(7) 0.0276(6) 0.0033(5) -0.0091(5) -0.0086(5)
  C15 0.0261(6) 0.0350(7) 0.0286(6) 0.0032(5) -0.0098(5) -0.0040(5)
  C16 0.0252(6) 0.0375(7) 0.0318(7) -0.0023(5) -0.0084(5) -0.0052(6)
  C17 0.0209(6) 0.0400(7) 0.0308(6) 0.0005(5) -0.0087(5) -0.0115(6)
  C18 0.0224(6) 0.0341(7) 0.0356(7) -0.0009(5) -0.0118(5) -0.0074(6)
  N1 0.0255(6) 0.0219(6) 0.0349(7) -0.0007(5) -0.0110(5) -0.0096(5)
  C2 0.0241(9) 0.0317(10) 0.0456(11) 0.0062(7) -0.0181(8) -0.0149(9)
  C3 0.0389(9) 0.0276(8) 0.0455(13) 0.0089(7) -0.0257(10) -0.0153(8)
  N4 0.0271(7) 0.0177(9) 0.0388(14) -0.0008(7) -0.0183(8) -0.0053(9)
  C5 0.0366(10) 0.0338(9) 0.0406(10) 0.0009(7) -0.0190(8) -0.0143(7)
  C51 0.0526(19) 0.0480(19) 0.0763(19) 0.0109(13) -0.0411(16) -0.0362(13)
  C52 0.046(2) 0.0639(16) 0.0441(12) 0.0048(13) -0.0167(11) -0.0016(11)
  C6 0.0405(12) 0.0286(17) 0.0493(12) 0.0029(11) -0.0210(10) -0.0191(13)
  C7 0.0319(9) 0.0299(8) 0.0369(9) 0.0049(7) -0.0131(7) -0.0148(8)
  C71 0.0546(14) 0.0400(12) 0.0732(16) 0.0215(9) -0.0341(13) -0.0312(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
  O1 C17 . 1.1974(18) y
  O2 H2 . 0.8400 ?
  O2 C17 . 1.3147(18) y
  O3 C18 . 1.2497(18) y
  O4 C18 . 1.2477(17) y
  O5 N11 . 1.2136(19) ?
  O6 N11 . 1.227(2) ?
  N11 C15 . 1.4752(19) ?
  C11 C12 . 1.3902(19) ?
  C11 C16 . 1.392(2) ?
  C11 C17 . 1.4984(18) ?
  C12 H12 . 0.9500 ?
  C12 C13 . 1.3948(17) ?
  C13 C14 . 1.3940(18) ?
  C13 C18 . 1.5149(19) ?
  C14 H14 . 0.9500 ?
  C14 C15 . 1.386(2) ?
  C15 C16 . 1.3858(19) ?
  C16 H16 . 0.9500 ?
  N1 H1 . 0.9200 ?
  N1 C2 . 1.475(2) y
  C2 H2A . 0.9900 ?
  C2 H2B . 0.9900 ?
  C2 C3 . 1.511(3) ?
  C3 H3A . 0.9900 ?
  C3 H3B . 0.9900 ?
  C3 N4 . 1.505(2) y
  N4 H4A . 0.9200 ?
  N4 H4B . 0.9200 ?
  N4 C5 . 1.530(3) y
  C5 C51 . 1.530(3) ?
  C5 C52 . 1.533(4) ?
  C5 C6 . 1.542(3) ?
  C51 H51A . 0.9800 ?
  C51 H51B . 0.9800 ?
  C51 H51C . 0.9800 ?
  C52 H52A . 0.9800 ?
  C52 H52B . 0.9800 ?
  C52 H52C . 0.9800 ?
  C6 H6A . 0.9900 ?
  C6 H6B . 0.9900 ?
  C6 C7 . 1.538(4) ?
  C7 H7 . 1.0000 ?
  C7 N1 2_666 1.484(2) y
  C7 C71 . 1.542(4) ?
  C71 H71A . 0.9800 ?
  C71 H71B . 0.9800 ?
  C71 H71C . 0.9800 ?
  N21 H21 . 0.9200 ?
  N21 C22 . 1.455(9) ?
  C22 H22A . 0.9900 ?
  C22 H22B . 0.9900 ?
  C22 C23 . 1.485(9) ?
  C23 H23A . 0.9900 ?
  C23 H23B . 0.9900 ?
  C23 N24 . 1.467(10) ?
  N24 H24A . 0.9200 ?
  N24 H24B . 0.9200 ?
  N24 C25 . 1.473(10) ?
  C25 C251 . 1.521(10) ?
  C25 C252 . 1.526(10) ?
  C25 C26 . 1.524(10) ?
  C251 H25A . 0.9800 ?
  C251 H25B . 0.9800 ?
  C251 H25C . 0.9800 ?
  C252 H25D . 0.9800 ?
  C252 H25E . 0.9800 ?
  C252 H25F . 0.9800 ?
  C26 H26A . 0.9900 ?
  C26 H26B . 0.9900 ?
  C26 C27 . 1.524(10) ?
  C27 H27 . 1.0000 ?
  C27 C271 . 1.523(10) ?
  C271 H27A . 0.9800 ?
  C271 H27B . 0.9800 ?
  C271 H27C . 0.9800 ?
_cod_database_code 2012910