#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2010329.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_2010329
_journal_name_full  'Acta Crystallographica'
_journal_year  1994
_journal_volume  C50
_journal_page_first  1982
_journal_page_last  1985
_publ_section_title
;
 Tetraaza[3.3.3.3]- and
 Hexaaza[3.3.3.3.3.3]Paracyclophane Derivatives
;
loop_
_publ_author_name
  'Tinant, Bernard'
  'Declercq, Jean-Paul'
  'Lepropre, Guy'
  'Fastrez, Jacques'
_chemical_formula_moiety  'C66 H78 N6 O12'
_chemical_formula_sum  'C66 H78 N6 O12'
_chemical_formula_weight  1147.34
_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  18.075(3)
_cell_length_b  17.946(2)
_cell_length_c  9.658(2)
_cell_angle_alpha  90.00
_cell_angle_beta  90.040(10)
_cell_angle_gamma  90.00
_cell_volume  3132.8(9)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.216
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.0564
_refine_ls_wR_factor_obs  0.1512
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  N1 0.73910(10) 0.64184(10) 0.1396(2) 0.0561(5) Uani d . 1 . N
  C2 0.7821(2) 0.57360(14) 0.1349(3) 0.0637(7) Uani d . 1 . C
  C3 0.80668(14) 0.54745(12) 0.2756(2) 0.0554(6) Uani d . 1 . C
  C4 0.7597(2) 0.55048(14) 0.3888(3) 0.0626(7) Uani d . 1 . C
  C5 0.7805(2) 0.52158(14) 0.5156(3) 0.0646(7) Uani d . 1 . C
  C6 0.84883(14) 0.48851(12) 0.5333(3) 0.0576(6) Uani d . 1 . C
  C7 0.8956(2) 0.48605(14) 0.4213(3) 0.0634(7) Uani d . 1 . C
  C8 0.87535(15) 0.51574(14) 0.2941(3) 0.0623(6) Uani d . 1 . C
  C9 0.8709(2) 0.4570(2) 0.6724(3) 0.0682(7) Uani d . 1 . C
  N10 0.82533(11) 0.39284(10) 0.7108(2) 0.0559(5) Uani d . 1 . N
  C11 0.8425(2) 0.32696(14) 0.6251(3) 0.0579(6) Uani d . 1 . C
  C12 0.78607(13) 0.26627(12) 0.6404(2) 0.0494(5) Uani d . 1 . C
  C13 0.71672(14) 0.27377(14) 0.5810(3) 0.0586(6) Uani d . 1 . C
  C14 0.66437(14) 0.21875(14) 0.5917(3) 0.0597(6) Uani d . 1 . C
  C15 0.67889(13) 0.15333(12) 0.6625(2) 0.0536(6) Uani d . 1 . C
  C16 0.74819(14) 0.14569(13) 0.7223(3) 0.0564(6) Uani d . 1 . C
  C17 0.80085(14) 0.20115(13) 0.7108(2) 0.0558(6) Uani d . 1 . C
  C18 0.62137(14) 0.09257(14) 0.6722(3) 0.0610(7) Uani d . 1 . C
  N19 0.54980(10) 0.12304(10) 0.7127(2) 0.0529(5) Uani d . 1 . N
  C20 0.54605(15) 0.1405(2) 0.8609(3) 0.0583(6) Uani d . 1 . C
  C21 0.48330(12) 0.19203(13) 0.8939(2) 0.0510(6) Uani d . 1 . C
  C22 0.47893(15) 0.26065(14) 0.8293(3) 0.0624(7) Uani d . 1 . C
  C23 0.42264(15) 0.30921(15) 0.8589(3) 0.0622(7) Uani d . 1 . C
  C24 0.36824(13) 0.29148(13) 0.9529(2) 0.0535(6) Uani d . 1 . C
  C25 0.3726(2) 0.2231(2) 1.0170(3) 0.0688(7) Uani d . 1 . C
  C26 0.42962(15) 0.1739(2) 0.9878(3) 0.0670(7) Uani d . 1 . C
  C27 0.69323(15) 0.6544(2) 0.0170(3) 0.0628(7) Uani d . 1 . C
  C28 0.7808(2) 0.70681(15) 0.1798(3) 0.0618(7) Uani d . 1 . C
  C29 0.8397(2) 0.7329(2) 0.0812(3) 0.0734(8) Uani d . 1 . C
  O30 0.85469(13) 0.70438(15) -0.0281(3) 0.1069(8) Uani d . 1 . O
  O31 0.87238(14) 0.79273(12) 0.1240(3) 0.1108(8) Uani d . 1 . O
  C32 0.9314(2) 0.8214(2) 0.0391(5) 0.131(2) Uani d . 1 . C
  H32A 0.9513(2) 0.8656(2) 0.0809(5) 0.0859(15) Uiso calc R 1 . H
  H32B 0.9126(2) 0.8332(2) -0.0513(5) 0.0859(15) Uiso calc R 1 . H
  H32C 0.9697(2) 0.7846(2) 0.0311(5) 0.0859(15) Uiso calc R 1 . H
  C33 0.8267(2) 0.3783(2) 0.8587(3) 0.0669(7) Uani d . 1 . C
  C34 0.9013(2) 0.3600(2) 0.9170(3) 0.0767(8) Uani d D 1 . C
  O35A 0.9639(14) 0.336(2)  0.8509(14) 0.167(13) Uani d PD 0.34(2) . O
  O35B 0.9268(4) 0.2993(2) 0.9036(9) 0.084(3) Uani d PD 0.66(2) . O
  O36 0.92589(11) 0.40933(13) 1.0023(3) 0.1010(7) Uani d . 1 . O
  C37 0.9966(2) 0.3941(3) 1.0674(5) 0.142(2) Uani d . 1 . C
  H37A 1.0093(2) 0.4344(3) 1.1283(5) 0.0859(15) Uiso calc R 1 . H
  H37B 1.0340(2) 0.3892(3) 0.9974(5) 0.0859(15) Uiso calc R 1 . H
  H37C 0.9934(2) 0.3486(3) 1.1194(5) 0.0859(15) Uiso calc R 1 . H
  C38 0.48551(15) 0.08500(14) 0.6621(3) 0.0576(6) Uani d . 1 . C
  C39 0.46934(15) 0.00932(14) 0.7222(3) 0.0598(6) Uani d . 1 . C
  O40 0.51120(11) -0.02780(10) 0.7877(2) 0.0908(7) Uani d . 1 . O
  O41 0.40068(10) -0.01186(10) 0.6923(2) 0.0817(6) Uani d . 1 . O
  C42 0.3772(2) -0.0827(2) 0.7450(4) 0.0957(10) Uani d . 1 . C
  H42A 0.3271(2) -0.0920(2) 0.7170(4) 0.0859(15) Uiso calc R 1 . H
  H42B 0.3801(2) -0.0824(2) 0.8442(4) 0.0859(15) Uiso calc R 1 . H
  H42C 0.4087(2) -0.1212(2) 0.7090(4) 0.0859(15) Uiso calc R 1 . H
  H2A 0.7497(16) 0.5369(16) 0.096(3)  0.0859(15) Uiso d . 1 . H
  H2B 0.8283(15) 0.5787(16) 0.072(3)  0.0859(15) Uiso d . 1 . H
  H4 0.7136(16) 0.5704(16) 0.377(3)  0.0859(15) Uiso d . 1 . H
  H5 0.7498(15) 0.5206(16) 0.597(3)  0.0859(15) Uiso d . 1 . H
  H7 0.9421(15) 0.4652(15) 0.431(3)  0.0859(15) Uiso d . 1 . H
  H8 0.9099(15) 0.5131(16) 0.212(3)  0.0859(15) Uiso d . 1 . H
  H9A 0.8650(14) 0.4950(17) 0.744(3)  0.0859(15) Uiso d . 1 . H
  H9B 0.9241(16) 0.4430(16) 0.668(3)  0.0859(15) Uiso d . 1 . H
  H11A 0.8424(15) 0.3420(15) 0.528(3)  0.0859(15) Uiso d . 1 . H
  H11B 0.8904(16) 0.3086(16) 0.650(3)  0.0859(15) Uiso d . 1 . H
  H13 0.7086(14) 0.3180(17) 0.533(3)  0.0859(15) Uiso d . 1 . H
  H14 0.6181(16) 0.2270(15) 0.549(3)  0.0859(15) Uiso d . 1 . H
  H16 0.7598(14) 0.1022(17) 0.780(3)  0.0859(15) Uiso d . 1 . H
  H17 0.8502(15) 0.1955(15) 0.755(3)  0.0859(15) Uiso d . 1 . H
  H18A 0.6389(14) 0.0533(16) 0.738(3)  0.0859(15) Uiso d . 1 . H
  H18B 0.6142(15) 0.0746(16) 0.582(3)  0.0859(15) Uiso d . 1 . H
  H20A 0.5920(17) 0.1655(16) 0.882(3)  0.0859(15) Uiso d . 1 . H
  H20B 0.5423(15) 0.0959(16) 0.921(3)  0.0859(15) Uiso d . 1 . H
  H22 0.5164(16) 0.2756(15) 0.762(3)  0.0859(15) Uiso d . 1 . H
  H23 0.4161(15) 0.3558(16) 0.814(3)  0.0859(15) Uiso d . 1 . H
  H25 0.3364(15) 0.2125(16) 1.085(3)  0.0859(15) Uiso d . 1 . H
  H26 0.4323(15) 0.1268(16) 1.034(3)  0.0859(15) Uiso d . 1 . H
  H27A 0.7245(15) 0.6718(15) -0.064(3)  0.0859(15) Uiso d . 1 . H
  H27B 0.6713(16) 0.6064(17) -0.003(3)  0.0859(15) Uiso d . 1 . H
  H28A 0.8055(15) 0.6952(16) 0.264(3)  0.0859(15) Uiso d . 1 . H
  H28B 0.7485(15) 0.7496(18) 0.194(3)  0.0859(15) Uiso d . 1 . H
  H33A 0.8075(15) 0.4207(17) 0.904(3)  0.0859(15) Uiso d . 1 . H
  H33B 0.7964(15) 0.3338(18) 0.880(3)  0.0859(15) Uiso d . 1 . H
  H38A 0.4417(16) 0.1144(16) 0.675(3)  0.0859(15) Uiso d . 1 . H
  H38B 0.4906(15) 0.0757(15) 0.563(3)  0.0859(15) Uiso d . 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
  N1 0.0633(12) 0.0513(11) 0.0538(11) 0.0084(9) -0.0067(9) -0.0015(9)
  C2 0.082(2) 0.0500(14) 0.059(2) 0.0120(14) -0.0031(13) 0.0009(12)
  C3 0.066(2) 0.0392(12) 0.0606(14) 0.0043(11) -0.0025(12) 0.0007(11)
  C4 0.065(2) 0.057(2) 0.066(2) 0.0116(13) 0.0020(13) 0.0071(12)
  C5 0.073(2) 0.061(2) 0.060(2) 0.0052(13) 0.0033(13) 0.0076(12)
  C6 0.063(2) 0.0408(12) 0.069(2) -0.0070(11) -0.0105(13) 0.0056(11)
  C7 0.056(2) 0.0554(15) 0.079(2) 0.0016(12) -0.0102(14) 0.0083(13)
  C8 0.062(2) 0.0537(14) 0.071(2) 0.0013(12) 0.0041(13) 0.0022(13)
  C9 0.080(2) 0.057(2) 0.068(2) -0.0091(14) -0.0174(15) 0.0069(13)
  N10 0.0699(13) 0.0446(11) 0.0531(11) -0.0003(9) -0.0056(9) 0.0026(9)
  C11 0.066(2) 0.0522(14) 0.0552(14) 0.0001(12) 0.0005(12) -0.0003(11)
  C12 0.0588(14) 0.0450(12) 0.0444(12) 0.0023(11) 0.0038(10) -0.0030(10)
  C13 0.068(2) 0.0496(14) 0.0584(15) 0.0062(13) 0.0001(12) 0.0105(11)
  C14 0.0561(15) 0.0553(15) 0.068(2) 0.0044(12) -0.0074(12) 0.0073(12)
  C15 0.0580(14) 0.0478(13) 0.0550(13) 0.0036(11) 0.0039(11) -0.0035(10)
  C16 0.064(2) 0.0444(13) 0.0610(15) 0.0070(12) 0.0004(12) 0.0046(11)
  C17 0.0574(14) 0.0524(14) 0.0577(14) 0.0040(12) -0.0042(11) 0.0006(11)
  C18 0.064(2) 0.0489(14) 0.070(2) 0.0010(12) 0.0031(13) -0.0026(12)
  N19 0.0536(11) 0.0528(11) 0.0523(11) -0.0002(9) -0.0047(9) -0.0032(9)
  C20 0.0558(15) 0.066(2) 0.0532(14) 0.0076(13) -0.0094(11) -0.0038(12)
  C21 0.0503(13) 0.0541(13) 0.0487(13) 0.0018(11) -0.0089(10) -0.0025(10)
  C22 0.062(2) 0.057(2) 0.068(2) -0.0032(13) 0.0102(13) 0.0012(12)
  C23 0.070(2) 0.0516(14) 0.065(2) -0.0007(13) 0.0009(13) 0.0065(12)
  C24 0.0571(14) 0.0579(14) 0.0456(12) 0.0029(11) -0.0081(11) -0.0026(11)
  C25 0.068(2) 0.074(2) 0.064(2) 0.0112(14) 0.0140(13) 0.0166(14)
  C26 0.070(2) 0.064(2) 0.066(2) 0.0091(14) 0.0058(13) 0.0192(13)
  C27 0.067(2) 0.069(2) 0.0530(15) 0.0115(14) -0.0076(12) -0.0034(13)
  C28 0.070(2) 0.0538(15) 0.061(2) 0.0060(13) -0.0094(13) 0.0001(12)
  C29 0.071(2) 0.066(2) 0.083(2) 0.0076(15) -0.010(2) 0.003(2)
  O30 0.097(2) 0.132(2) 0.091(2) -0.0151(14) 0.0137(13) 0.0015(15)
  O31 0.114(2) 0.0680(14) 0.150(2) -0.0204(13) 0.004(2) 0.0072(14)
  C32 0.100(3) 0.088(3) 0.206(5) -0.020(2) -0.009(3) 0.056(3)
  C33 0.090(2) 0.058(2) 0.0530(15) 0.0118(15) -0.0048(13) -0.0005(12)
  C34 0.099(2) 0.080(2) 0.051(2) 0.019(2) -0.010(2) -0.0006(14)
  O35A 0.136(13) 0.29(3)  0.080(6) 0.123(18) -0.017(7) -0.032(10)
  O35B 0.087(4) 0.067(3) 0.098(4) 0.024(2) -0.029(3) -0.006(2)
  O36 0.0724(13) 0.109(2) 0.122(2) 0.0065(12) -0.0204(12) -0.0451(14)
  C37 0.085(2) 0.150(4) 0.191(4) 0.017(2) -0.040(3) -0.061(3)
  C38 0.063(2) 0.0568(15) 0.0530(14) -0.0027(12) -0.0109(12) 0.0014(11)
  C39 0.063(2) 0.0547(14) 0.0616(15) 0.0008(13) -0.0040(12) -0.0002(12)
  O40 0.0798(13) 0.0638(11) 0.129(2) -0.0009(10) -0.0228(13) 0.0250(12)
  O41 0.0686(12) 0.0723(12) 0.1041(15) -0.0175(10) -0.0158(10) 0.0130(10)
  C42 0.090(2) 0.080(2) 0.118(3) -0.024(2) -0.001(2) 0.007(2)
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 C28 . 1.441(3) yes
  N1 C2 . 1.451(3) yes
  N1 C27 . 1.463(3) yes
  C2 C3 . 1.504(3) yes
  C2 H2A . 0.96(3) ?
  C2 H2B . 1.04(3) ?
  C3 C8 . 1.377(3) no
  C3 C4 . 1.386(3) no
  C4 C5 . 1.382(4) no
  C4 H4 . 0.91(3) ?
  C5 C6 . 1.381(3) no
  C5 H5 . 0.97(3) ?
  C6 C7 . 1.373(4) no
  C6 C9 . 1.511(4) yes
  C7 C8 . 1.388(4) no
  C7 H7 . 0.93(3) ?
  C8 H8 . 1.01(3) ?
  C9 N10 . 1.464(3) yes
  C9 H9A . 0.97(3) ?
  C9 H9B . 0.99(3) ?
  N10 C33 . 1.453(3) yes
  N10 C11 . 1.477(3) yes
  C11 C12 . 1.500(3) yes
  C11 H11A . 0.98(3) ?
  C11 H11B . 0.96(3) ?
  C12 C17 . 1.378(3) no
  C12 C13 . 1.385(3) no
  C13 C14 . 1.372(4) no
  C13 H13 . 0.93(3) ?
  C14 C15 . 1.384(3) no
  C14 H14 . 0.94(3) ?
  C15 C16 . 1.386(3) no
  C15 C18 . 1.510(3) yes
  C16 C17 . 1.382(3) no
  C16 H16 . 0.98(3) ?
  C17 H17 . 0.99(3) ?
  C18 N19 . 1.458(3) yes
  C18 H18A . 1.00(3) ?
  C18 H18B . 0.94(3) ?
  N19 C38 . 1.433(3) yes
  N19 C20 . 1.467(3) yes
  C20 C21 . 1.498(3) yes
  C20 H20A . 0.97(3) ?
  C20 H20B . 0.99(3) ?
  C21 C26 . 1.367(3) no
  C21 C22 . 1.383(3) no
  C22 C23 . 1.370(4) no
  C22 H22 . 0.98(3) ?
  C23 C24 . 1.376(3) no
  C23 H23 . 0.95(3) ?
  C24 C25 . 1.376(3) no
  C24 C27 3_666 1.504(3) yes
  C25 C26 . 1.387(4) no
  C25 H25 . 0.95(3) ?
  C26 H26 . 0.96(3) ?
  C27 C24 3_666 1.504(3) ?
  C27 H27A . 1.02(3) ?
  C27 H27B . 0.97(3) ?
  C28 C29 . 1.504(4) yes
  C28 H28A . 0.95(3) ?
  C28 H28B . 0.97(3) ?
  C29 O30 . 1.203(3) yes
  C29 O31 . 1.293(3) yes
  O31 C32 . 1.441(4) yes
  C32 H32A . 0.96 ?
  C32 H32B . 0.96 ?
  C32 H32C . 0.96 ?
  C33 C34 . 1.498(4) yes
  C33 H33A . 0.94(3) ?
  C33 H33B . 0.99(3) ?
  C34 O35B . 1.190(5) yes
  C34 O36 . 1.288(3) yes
  C34 O35A . 1.37(2) ?
  O35A O35B . 1.07(4) ?
  O36 C37 . 1.450(4) yes
  C37 H37A . 0.96 ?
  C37 H37B . 0.96 ?
  C37 H37C . 0.96 ?
  C38 C39 . 1.506(4) yes
  C38 H38A . 0.96(3) ?
  C38 H38B . 0.98(3) ?
  C39 O40 . 1.189(3) yes
  C39 O41 . 1.330(3) yes
  O41 C42 . 1.434(3) yes
  C42 H42A . 0.96 ?
  C42 H42B . 0.96 ?
  C42 H42C . 0.96 ?