#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013369.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_2013369
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o329
_journal_page_last  o331
_publ_section_title
;
meso-5,5,7,12,12,14-Hexamethyl-4,11-diaza-1,8-diazoniacyclotetradecane
(S)-malate(2-) methanol disolvate: a chain of rings generated by two
pairs of N---H...O hydrogen bonds
;
loop_
_publ_author_name
  'Bowes, Katharine F.'
  'Ferguson, George'
  'Lough, Alan J.'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C16 H38 N4 2+, C4 H4 O5 2-, 2C H4 O'
_chemical_formula_sum  'C22 H50 N4 O7'
_chemical_formula_iupac  'C16 H38 N4 2+, C4 H4 O5 2-, 2C H4 O'
_chemical_formula_weight  482.66
_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'
_cell_length_a  8.6559(9)
_cell_length_b  9.3275(9)
_cell_length_c  10.1044(12)
_cell_angle_alpha  113.379(5)
_cell_angle_beta  108.908(4)
_cell_angle_gamma  100.345(4)
_cell_volume  662.31(12)
_cell_formula_units_Z  1
_cell_measurement_temperature  150.0(10)
_exptl_crystal_density_diffrn  1.210
_diffrn_ambient_temperature  150.0(10)
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 0.3490(7) 0.5886(7) 0.6152(6) 0.0348(12) Uani d . 1 . . N
  C2 0.2646(9) 0.6456(9) 0.5044(8) 0.0417(17) Uani d . 1 . . C
  C3 0.2031(9) 0.5122(10) 0.3277(9) 0.0454(18) Uani d . 1 . . C
  N4 0.3509(7) 0.4851(7) 0.2942(6) 0.0351(13) Uani d . 1 . . N
  C5 0.3038(9) 0.3576(8) 0.1258(8) 0.0427(17) Uani d . 1 . . C
  C51 0.2029(11) 0.4108(11) 0.0063(8) 0.052(2) Uani d . 1 . . C
  C52 0.1843(9) 0.1879(9) 0.0882(9) 0.051(2) Uani d . 1 . . C
  C6 0.4699(9) 0.3468(8) 0.1112(7) 0.0409(17) Uani d . 1 . . C
  C7 0.5846(9) 0.2865(9) 0.2113(8) 0.0392(16) Uani d . 1 . . C
  C71 0.7346(11) 0.2657(11) 0.1687(10) 0.054(2) Uani d . 1 . . C
  N8 0.6494(8) 0.4112(7) 0.3859(6) 0.0406(14) Uani d . 1 . . N
  C9 0.7363(9) 0.3547(9) 0.5016(8) 0.0429(18) Uani d . 1 . . C
  C10 0.8003(8) 0.4854(9) 0.6700(8) 0.0396(16) Uani d . 1 . . C
  N11 0.6540(7) 0.5162(8) 0.7066(6) 0.0395(14) Uani d . 1 . . N
  C12 0.7037(8) 0.6402(9) 0.8750(8) 0.0406(17) Uani d . 1 . . C
  C121 0.7940(10) 0.5848(12) 0.9938(9) 0.057(2) Uani d . 1 . . C
  C122 0.8195(10) 0.8099(10) 0.9186(10) 0.057(2) Uani d . 1 . . C
  C13 0.5337(9) 0.6519(9) 0.8909(8) 0.0427(18) Uani d . 1 . . C
  C14 0.4196(9) 0.7124(9) 0.7900(8) 0.0404(16) Uani d . 1 . . C
  C141 0.2675(10) 0.7357(11) 0.8319(10) 0.055(2) Uani d . 1 . . C
  O21 0.8761(18) 0.6984(15) 0.4528(14) 0.055(3) Uani d PD 0.702(8) A -1 O
  O22 0.6487(12) 0.767(2) 0.352(2) 0.060(3) Uani d PD 0.702(8) A -1 O
  O23 1.1226(15) 1.2848(13) 0.5314(17) 0.053(2) Uani d PD 0.702(8) A -1 O
  O24 1.3506(8) 1.2325(8) 0.6507(9) 0.0422(17) Uani d PD 0.702(8) A -1 O
  O25 0.8473(7) 0.9921(7) 0.3250(7) 0.0543(16) Uani d P 0.702(8) A -1 O
  C21 0.8080(11) 0.7899(11) 0.4108(12) 0.042(3) Uani d PD 0.702(8) A -1 C
  C22 0.9351(13) 0.9296(15) 0.4161(15) 0.0670(17) Uani d PD 0.702(8) A -1 C
  C23 1.0659(14) 1.0562(15) 0.5800(15) 0.0670(17) Uani d PD 0.702(8) A -1 C
  C24 1.1900(8) 1.2041(11) 0.5920(12) 0.045(3) Uani d PD 0.702(8) A -1 C
  O41 0.4707(9) 0.9442(8) 0.2526(8) 0.0758(19) Uani d . 1 B -1 O
  C42 0.3300(13) 0.8999(12) 0.2782(10) 0.069(2) Uani d . 1 B -1 C
  O51 1.5287(9) 1.0569(8) 0.7487(8) 0.0758(18) Uani d . 1 . . O
  C53 1.6701(12) 1.0910(10) 0.7186(10) 0.063(2) Uani d . 1 . . C
  C31 0.829(3) 0.820(3) 0.461(3) 0.074(3) Uiso d PD 0.298(8) A -2 C
  C32 0.956(2) 0.995(3) 0.538(2) 0.074(3) Uiso d PD 0.298(8) A -2 C
  C33 1.062(3) 1.010(2) 0.450(2) 0.074(3) Uiso d PD 0.298(8) A -2 C
  C34 1.179(2) 1.186(2) 0.519(2) 0.074(3) Uiso d PD 0.298(8) A -2 C
  O31 0.891(6) 0.719(5) 0.490(5) 0.074(3) Uiso d PD 0.298(8) A -2 O
  O32 0.671(4) 0.782(6) 0.372(6) 0.074(3) Uiso d PD 0.298(8) A -2 O
  O33 1.127(5) 1.305(4) 0.531(4) 0.074(3) Uiso d PD 0.298(8) A -2 O
  O34 1.337(2) 1.203(2) 0.561(2) 0.074(3) Uiso d PD 0.298(8) A -2 O
  O35 1.100(2) 1.028(2) 0.679(2) 0.074(3) Uiso d PD 0.298(8) A -2 O
  H1A 0.4394 0.5615 0.5957 0.042 Uiso calc R 1 . . H
  H1B 0.2694 0.4927 0.5932 0.042 Uiso calc R 1 . . H
  H2A 0.3479 0.7505 0.5285 0.050 Uiso calc R 1 . . H
  H2B 0.1629 0.6693 0.5198 0.050 Uiso calc R 1 . . H
  H3A 0.1248 0.4056 0.3055 0.054 Uiso calc R 1 . . H
  H3B 0.1357 0.5488 0.2557 0.054 Uiso calc R 1 . . H
  H4 0.4233 0.5853 0.3166 0.042 Uiso calc R 1 . . H
  H51A 0.0864 0.3997 0.0020 0.078 Uiso calc R 1 . . H
  H51B 0.1917 0.3389 -0.1006 0.078 Uiso calc R 1 . . H
  H51C 0.2669 0.5273 0.0421 0.078 Uiso calc R 1 . . H
  H52A 0.2320 0.1680 0.1788 0.076 Uiso calc R 1 . . H
  H52B 0.1787 0.0981 -0.0083 0.076 Uiso calc R 1 . . H
  H52C 0.0667 0.1901 0.0702 0.076 Uiso calc R 1 . . H
  H6A 0.5417 0.4591 0.1393 0.049 Uiso calc R 1 . . H
  H6B 0.4379 0.2715 -0.0029 0.049 Uiso calc R 1 . . H
  H7 0.5120 0.1761 0.1891 0.047 Uiso calc R 1 . . H
  H71A 0.8043 0.3725 0.1864 0.082 Uiso calc R 1 . . H
  H71B 0.6883 0.1812 0.0558 0.082 Uiso calc R 1 . . H
  H71C 0.8083 0.2301 0.2365 0.082 Uiso calc R 1 . . H
  H8A 0.7276 0.5086 0.4090 0.049 Uiso calc R 1 . . H
  H8B 0.5564 0.4351 0.4021 0.049 Uiso calc R 1 . . H
  H9A 0.6518 0.2523 0.4807 0.052 Uiso calc R 1 . . H
  H9B 0.8356 0.3269 0.4841 0.052 Uiso calc R 1 . . H
  H10A 0.8688 0.4500 0.7427 0.048 Uiso calc R 1 . . H
  H10B 0.8784 0.5903 0.6890 0.048 Uiso calc R 1 . . H
  H11 0.5790 0.4165 0.6825 0.047 Uiso calc R 1 . . H
  H12A 0.9022 0.5736 0.9875 0.086 Uiso calc R 1 . . H
  H12B 0.7162 0.4771 0.9670 0.086 Uiso calc R 1 . . H
  H12C 0.8214 0.6684 1.1028 0.086 Uiso calc R 1 . . H
  H12D 0.9325 0.8051 0.9210 0.086 Uiso calc R 1 . . H
  H12E 0.8375 0.8932 1.0245 0.086 Uiso calc R 1 . . H
  H12F 0.7634 0.8413 0.8386 0.086 Uiso calc R 1 . . H
  H13A 0.4617 0.5399 0.8632 0.051 Uiso calc R 1 . . H
  H13B 0.5661 0.7278 1.0049 0.051 Uiso calc R 1 . . H
  H14 0.4930 0.8220 0.8112 0.048 Uiso calc R 1 . . H
  H14A 0.2035 0.7844 0.7728 0.082 Uiso calc R 1 . . H
  H14B 0.3131 0.8105 0.9474 0.082 Uiso calc R 1 . . H
  H14C 0.1886 0.6271 0.8022 0.082 Uiso calc R 1 . . H
  H25 0.9017 1.0949 0.3674 0.081 Uiso calc PR 0.702(8) A -1 H
  H22 1.0025 0.8756 0.3607 0.080 Uiso calc PR 0.702(8) A -1 H
  H23A 1.1360 1.0012 0.6275 0.080 Uiso calc PR 0.702(8) A -1 H
  H23B 1.0038 1.0989 0.6452 0.080 Uiso calc PR 0.702(8) A -1 H
  H41 0.5415 0.9003 0.2832 0.114 Uiso calc R 1 B -1 H
  H42D 0.3664 0.9442 0.3935 0.103 Uiso calc R 1 B -1 H
  H42E 0.2773 0.7778 0.2229 0.103 Uiso calc R 1 B -1 H
  H42F 0.2443 0.9455 0.2367 0.103 Uiso calc R 1 B -1 H
  H51 1.4668 1.1114 0.7266 0.114 Uiso calc R 1 . . H
  H53A 1.6645 1.1695 0.6769 0.095 Uiso calc R 1 . . H
  H53B 1.6697 0.9873 0.6393 0.095 Uiso calc R 1 . . H
  H53C 1.7776 1.1407 0.8182 0.095 Uiso calc R 1 . . H
  H32 0.8992 1.0809 0.5596 0.089 Uiso calc PR 0.298(8) A -2 H
  H33A 1.1340 0.9393 0.4530 0.089 Uiso calc PR 0.298(8) A -2 H
  H33B 0.9819 0.9676 0.3363 0.089 Uiso calc PR 0.298(8) A -2 H
  H35 1.0814 0.9467 0.6964 0.111 Uiso calc PRD 0.298(8) 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
  N1 0.026(3) 0.034(3) 0.038(3) 0.012(2) 0.012(2) 0.014(2)
  C2 0.033(4) 0.044(4) 0.052(4) 0.016(3) 0.018(3) 0.026(4)
  C3 0.035(4) 0.049(4) 0.045(4) 0.014(3) 0.012(3) 0.022(4)
  N4 0.027(3) 0.031(3) 0.043(3) 0.006(2) 0.014(3) 0.017(3)
  C5 0.046(4) 0.036(4) 0.047(4) 0.016(3) 0.023(4) 0.019(3)
  C51 0.067(5) 0.057(5) 0.036(4) 0.027(4) 0.024(4) 0.023(4)
  C52 0.042(4) 0.029(3) 0.063(5) -0.001(3) 0.019(4) 0.014(3)
  C6 0.037(4) 0.034(4) 0.037(4) 0.006(3) 0.012(3) 0.011(3)
  C7 0.038(4) 0.035(3) 0.042(4) 0.008(3) 0.017(3) 0.018(3)
  C71 0.060(5) 0.065(5) 0.058(5) 0.038(5) 0.032(5) 0.037(5)
  N8 0.041(3) 0.041(3) 0.045(3) 0.013(3) 0.017(3) 0.028(3)
  C9 0.044(4) 0.050(4) 0.046(4) 0.024(3) 0.018(3) 0.031(4)
  C10 0.026(4) 0.049(4) 0.047(4) 0.013(3) 0.013(3) 0.029(4)
  N11 0.033(3) 0.041(3) 0.041(3) 0.010(2) 0.012(3) 0.022(3)
  C12 0.027(3) 0.043(4) 0.038(4) 0.006(3) 0.002(3) 0.019(3)
  C121 0.042(4) 0.074(5) 0.056(5) 0.027(4) 0.009(4) 0.039(4)
  C122 0.044(5) 0.055(5) 0.062(5) 0.014(4) 0.016(4) 0.025(4)
  C13 0.048(5) 0.050(4) 0.042(4) 0.021(3) 0.020(4) 0.032(4)
  C14 0.039(4) 0.042(4) 0.044(4) 0.020(3) 0.018(3) 0.022(3)
  C141 0.048(5) 0.073(6) 0.047(5) 0.026(4) 0.022(4) 0.029(4)
  O21 0.039(4) 0.047(5) 0.075(7) 0.003(4) 0.017(5) 0.039(5)
  O22 0.040(5) 0.039(5) 0.087(8) 0.007(4) 0.018(5) 0.029(6)
  O23 0.030(4) 0.035(4) 0.082(5) 0.000(3) 0.010(3) 0.034(4)
  O24 0.039(4) 0.029(3) 0.050(4) 0.006(3) 0.019(3) 0.015(3)
  O25 0.044(3) 0.045(3) 0.058(3) 0.006(2) 0.005(2) 0.029(3)
  C21 0.050(7) 0.025(5) 0.046(6) -0.002(4) 0.025(5) 0.018(5)
  C22 0.047(3) 0.065(3) 0.064(3) -0.013(2) -0.003(2) 0.045(3)
  C23 0.047(3) 0.065(3) 0.064(3) -0.013(2) -0.003(2) 0.045(3)
  C24 0.027(5) 0.041(5) 0.045(6) 0.002(4) 0.002(4) 0.016(5)
  O41 0.071(5) 0.068(4) 0.075(4) 0.017(3) 0.015(3) 0.041(4)
  C42 0.068(6) 0.061(5) 0.059(5) 0.017(5) 0.017(5) 0.024(5)
  O51 0.086(5) 0.071(4) 0.083(4) 0.025(4) 0.039(4) 0.048(4)
  C53 0.083(7) 0.053(5) 0.069(6) 0.027(5) 0.034(5) 0.043(5)
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 C2 . 1.466(7) no
  N1 C14 . 1.502(8) no
  N1 H1A . 0.92 no
  N1 H1B . 0.92 no
  C2 C3 . 1.550(9) no
  C2 H2A . 0.99 no
  C2 H2B . 0.99 no
  C3 N4 . 1.465(8) no
  C3 H3A . 0.99 no
  C3 H3B . 0.99 no
  N4 C5 . 1.499(8) no
  N4 H4 . 0.92 no
  C5 C6 . 1.509(9) no
  C5 C52 . 1.549(9) no
  C5 C51 . 1.554(9) no
  C51 H51A . 0.98 no
  C51 H51B . 0.98 no
  C51 H51C . 0.98 no
  C52 H52A . 0.98 no
  C52 H52B . 0.98 no
  C52 H52C . 0.98 no
  C6 C7 . 1.525(9) no
  C6 H6A . 0.99 no
  C6 H6B . 0.99 no
  C7 N8 . 1.509(9) no
  C7 C71 . 1.515(10) no
  C7 H7 . 1.00 no
  C71 H71A . 0.98 no
  C71 H71B . 0.98 no
  C71 H71C . 0.98 no
  N8 C9 . 1.507(7) no
  N8 H8A . 0.92 no
  N8 H8B . 0.92 no
  C9 C10 . 1.480(9) no
  C9 H9A . 0.99 no
  C9 H9B . 0.99 no
  C10 N11 . 1.474(8) no
  C10 H10A . 0.99 no
  C10 H10B . 0.99 no
  N11 C12 . 1.484(8) no
  N11 H11 . 0.92 no
  C12 C122 . 1.515(10) no
  C12 C121 . 1.531(8) no
  C12 C13 . 1.549(9) no
  C121 H12A . 0.98 no
  C121 H12B . 0.98 no
  C121 H12C . 0.98 no
  C122 H12D . 0.98 no
  C122 H12E . 0.98 no
  C122 H12F . 0.98 no
  C13 C14 . 1.529(9) no
  C13 H13A . 0.99 no
  C13 H13B . 0.99 no
  C14 C141 . 1.533(10) no
  C14 H14 . 1.00 no
  C141 H14A . 0.98 no
  C141 H14B . 0.98 no
  C141 H14C . 0.98 no
  O21 C21 . 1.250(5) no
  O22 C21 . 1.250(5) no
  O23 C24 . 1.254(5) no
  O24 C24 . 1.250(5) no
  O25 C22 . 1.377(11) no
  O25 H25 . 0.84 no
  C21 C22 . 1.518(7) no
  C22 C23 . 1.474(7) no
  C22 H22 . 1.00 no
  C23 C24 . 1.524(8) no
  C23 H23A . 0.99 no
  C23 H23B . 0.99 no
  O41 C42 . 1.352(10) no
  O41 H41 . 0.84 no
  C42 H42D . 0.98 no
  C42 H42E . 0.98 no
  C42 H42F . 0.98 no
  O51 C53 . 1.367(9) no
  O51 H51 . 0.84 no
  C53 H53A . 0.98 no
  C53 H53B . 0.98 no
  C53 H53C . 0.98 no
  C31 O31 . 1.250(5) no
  C31 O32 . 1.251(5) no
  C31 C32 . 1.504(5) no
  C32 O35 . 1.432(10) no
  C32 C33 . 1.498(5) no
  C32 H32 . 1.00 no
  C33 C34 . 1.498(5) no
  C33 H33A . 0.99 no
  C33 H33B . 0.99 no
  C34 O33 . 1.249(5) no
  C34 O34 . 1.249(5) no
  O35 H35 . 0.84 no