#------------------------------------------------------------------------------
#$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/23/2202321.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_2202321
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1098
_journal_page_last  o1100
_publ_section_title
;
A tetrakis(secondary amide) derivative of quadricyclane:
3-isopropylidenetetracyclo[3.2.0.0^2,7^.0^4,5^]heptane-
1,5,6,7-tetracarboxylic acid tetrakis(cyclohexylamide)
;
loop_
_publ_author_name
  'Winkler, Torsten'
  'Herges, Rainer'
  'Jones, Peter G.'
  'Dix, Ina'
_chemical_formula_moiety  'C38 H56 N4 O4'
_chemical_formula_sum  'C38 H56 N4 O4'
_chemical_formula_iupac  'C38 H56 N4 O4'
_chemical_formula_weight  632.87
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  10.1995(14)
_cell_length_b  11.6467(16)
_cell_length_c  15.206(2)
_cell_angle_alpha  87.126(3)
_cell_angle_beta  77.132(3)
_cell_angle_gamma  81.300(3)
_cell_volume  1740.5(4)
_cell_formula_units_Z  2
_cell_measurement_temperature  143(2)
_exptl_crystal_density_diffrn  1.208
_diffrn_ambient_temperature  143(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 0.15459(11) 0.39917(8) 0.16088(7) 0.0287(2) Uani d . 1 . . O
  O2 0.34661(11) 0.20025(8) 0.38288(7) 0.0292(2) Uani d . 1 . . O
  O3 0.61172(10) 0.49388(8) 0.38177(6) 0.0249(2) Uani d . 1 . . O
  O4 0.42131(10) 0.68948(9) 0.15772(7) 0.0290(2) Uani d . 1 . . O
  N1 0.22496(12) 0.24171(10) 0.24092(8) 0.0237(3) Uani d . 1 . . N
  H01 0.2594(18) 0.2184(15) 0.2895(12) 0.041(5) Uiso d . 1 . . H
  N2 0.51995(12) 0.27909(11) 0.41313(8) 0.0254(3) Uani d . 1 . . N
  H02 0.5586(17) 0.3438(16) 0.4091(11) 0.038(5) Uiso d . 1 . . H
  N3 0.59840(12) 0.62321(11) 0.26646(8) 0.0251(3) Uani d . 1 . . N
  H03 0.5415(17) 0.6567(14) 0.2296(11) 0.034(4) Uiso d . 1 . . H
  N4 0.28627(12) 0.58752(10) 0.10339(7) 0.0225(3) Uani d . 1 . . N
  H04 0.2337(19) 0.5252(16) 0.1158(12) 0.047(5) Uiso d . 1 . . H
  C1 0.25948(13) 0.42979(12) 0.28042(9) 0.0203(3) Uani d . 1 . . C
  C2 0.17811(14) 0.54797(11) 0.30926(9) 0.0198(3) Uani d . 1 . . C
  H2 0.0987 0.5802 0.2827 0.024 Uiso calc R 1 . . H
  C3 0.17503(13) 0.56681(11) 0.40519(9) 0.0189(3) Uani d . 1 . . C
  C4 0.30991(13) 0.50526(11) 0.41309(9) 0.0191(3) Uani d . 1 . . C
  H4 0.3394 0.5026 0.4717 0.023 Uiso calc R 1 . . H
  C5 0.35107(14) 0.40152(11) 0.35031(9) 0.0199(3) Uani d . 1 . . C
  C6 0.41198(13) 0.51615(12) 0.32369(8) 0.0203(3) Uani d . 1 . . C
  C7 0.32190(14) 0.54361(12) 0.25335(9) 0.0204(3) Uani d . 1 . . C
  C8 0.07612(14) 0.62359(11) 0.46717(9) 0.0212(3) Uani d . 1 . . C
  C9 0.08406(15) 0.63024(13) 0.56416(9) 0.0258(3) Uani d . 1 . . C
  H9A 0.1723 0.5903 0.5724 0.031 Uiso calc R 1 . . H
  H9B 0.0113 0.5929 0.6026 0.031 Uiso calc R 1 . . H
  H9C 0.0738 0.7118 0.5808 0.031 Uiso calc R 1 . . H
  C10 -0.05349(15) 0.68437(13) 0.44507(10) 0.0295(3) Uani d . 1 . . C
  H10A -0.0458 0.6843 0.3797 0.035 Uiso calc R 1 . . H
  H10B -0.0701 0.7647 0.4658 0.035 Uiso calc R 1 . . H
  H10C -0.1292 0.6438 0.4753 0.035 Uiso calc R 1 . . H
  C11 0.20902(13) 0.35430(12) 0.22199(9) 0.0200(3) Uani d . 1 . . C
  C12 0.18365(14) 0.15460(12) 0.19075(9) 0.0239(3) Uani d . 1 . . C
  H12 0.1640 0.1912 0.1333 0.029 Uiso calc R 1 . . H
  C13 0.30049(16) 0.05515(13) 0.16765(11) 0.0333(4) Uani d . 1 . . C
  H13A 0.3289 0.0252 0.2236 0.040 Uiso calc R 1 . . H
  H13B 0.3789 0.0846 0.1272 0.040 Uiso calc R 1 . . H
  C14 0.26051(17) -0.04366(14) 0.12184(12) 0.0378(4) Uani d . 1 . . C
  H14A 0.2435 -0.0164 0.0621 0.045 Uiso calc R 1 . . H
  H14B 0.3365 -0.1088 0.1121 0.045 Uiso calc R 1 . . H
  C15 0.13397(18) -0.08646(13) 0.17825(11) 0.0374(4) Uani d . 1 . . C
  H15A 0.1080 -0.1477 0.1454 0.045 Uiso calc R 1 . . H
  H15B 0.1534 -0.1207 0.2357 0.045 Uiso calc R 1 . . H
  C16 0.01751(17) 0.01281(14) 0.19792(11) 0.0356(4) Uani d . 1 . . C
  H16A -0.0628 -0.0159 0.2368 0.043 Uiso calc R 1 . . H
  H16B -0.0072 0.0423 0.1407 0.043 Uiso calc R 1 . . H
  C17 0.05586(16) 0.11165(13) 0.24489(10) 0.0306(3) Uani d . 1 . . C
  H17A -0.0201 0.1768 0.2536 0.037 Uiso calc R 1 . . H
  H17B 0.0705 0.0843 0.3051 0.037 Uiso calc R 1 . . H
  C18 0.40760(14) 0.28438(12) 0.38233(8) 0.0199(3) Uani d . 1 . . C
  C19 0.57800(14) 0.17537(12) 0.45736(9) 0.0222(3) Uani d . 1 . . C
  H19 0.5069 0.1231 0.4756 0.027 Uiso calc R 1 . . H
  C20 0.70010(16) 0.10923(13) 0.39436(10) 0.0295(3) Uani d . 1 . . C
  H20A 0.7675 0.1623 0.3707 0.035 Uiso calc R 1 . . H
  H20B 0.6707 0.0811 0.3425 0.035 Uiso calc R 1 . . H
  C21 0.76632(17) 0.00616(14) 0.44261(10) 0.0342(4) Uani d . 1 . . C
  H21A 0.7033 -0.0522 0.4583 0.041 Uiso calc R 1 . . H
  H21B 0.8497 -0.0305 0.4013 0.041 Uiso calc R 1 . . H
  C22 0.80250(17) 0.04123(15) 0.52738(12) 0.0401(4) Uani d . 1 . . C
  H22A 0.8748 0.0914 0.5112 0.048 Uiso calc R 1 . . H
  H22B 0.8383 -0.0290 0.5589 0.048 Uiso calc R 1 . . H
  C23 0.68006(19) 0.10589(14) 0.58981(11) 0.0390(4) Uani d . 1 . . C
  H23A 0.7079 0.1322 0.6429 0.047 Uiso calc R 1 . . H
  H23B 0.6118 0.0529 0.6114 0.047 Uiso calc R 1 . . H
  C24 0.61671(17) 0.21061(13) 0.54174(9) 0.0293(3) Uani d . 1 . . C
  H24A 0.5347 0.2494 0.5832 0.035 Uiso calc R 1 . . H
  H24B 0.6821 0.2669 0.5252 0.035 Uiso calc R 1 . . H
  C25 0.55041(13) 0.54306(12) 0.32541(9) 0.0199(3) Uani d . 1 . . C
  C26 0.73020(15) 0.66198(14) 0.26104(10) 0.0312(4) Uani d . 1 . . C
  H26 0.7704 0.6242 0.3114 0.037 Uiso calc R 1 . . H
  C27 0.71256(19) 0.79387(16) 0.27086(12) 0.0451(4) Uani d . 1 . . C
  H27A 0.6444 0.8165 0.3268 0.054 Uiso calc R 1 . . H
  H27B 0.7999 0.8169 0.2764 0.054 Uiso calc R 1 . . H
  C28 0.6670(2) 0.85841(16) 0.19085(16) 0.0580(6) Uani d . 1 . . C
  H28A 0.6644 0.9429 0.1974 0.070 Uiso calc R 1 . . H
  H28B 0.5741 0.8441 0.1901 0.070 Uiso calc R 1 . . H
  C29 0.7632(2) 0.81915(19) 0.10185(14) 0.0592(6) Uani d . 1 . . C
  H29A 0.7268 0.8575 0.0509 0.071 Uiso calc R 1 . . H
  H29B 0.8530 0.8432 0.0991 0.071 Uiso calc R 1 . . H
  C30 0.77975(18) 0.68988(18) 0.09251(11) 0.0465(5) Uani d . 1 . . C
  H30A 0.8468 0.6667 0.0362 0.056 Uiso calc R 1 . . H
  H30B 0.6919 0.6667 0.0883 0.056 Uiso calc R 1 . . H
  C31 0.82703(16) 0.62738(16) 0.17207(11) 0.0387(4) Uani d . 1 . . C
  H31A 0.9184 0.6456 0.1732 0.046 Uiso calc R 1 . . H
  H31B 0.8346 0.5425 0.1647 0.046 Uiso calc R 1 . . H
  C32 0.34906(14) 0.61144(12) 0.16647(9) 0.0209(3) Uani d . 1 . . C
  C33 0.28573(14) 0.65902(12) 0.02159(8) 0.0212(3) Uani d . 1 . . C
  H33 0.2791 0.7420 0.0382 0.025 Uiso calc R 1 . . H
  C34 0.16058(16) 0.64622(16) -0.01210(10) 0.0366(4) Uani d . 1 . . C
  H34A 0.0788 0.6685 0.0360 0.044 Uiso calc R 1 . . H
  H34B 0.1630 0.5639 -0.0266 0.044 Uiso calc R 1 . . H
  C35 0.15090(18) 0.7216(2) -0.09558(11) 0.0500(5) Uani d . 1 . . C
  H35A 0.0724 0.7057 -0.1190 0.060 Uiso calc R 1 . . H
  H35B 0.1349 0.8044 -0.0789 0.060 Uiso calc R 1 . . H
  C36 0.27857(18) 0.69924(17) -0.16885(10) 0.0420(4) Uani d . 1 . . C
  H36A 0.2866 0.6203 -0.1926 0.050 Uiso calc R 1 . . H
  H36B 0.2721 0.7557 -0.2191 0.050 Uiso calc R 1 . . H
  C37 0.40359(17) 0.70969(16) -0.13409(10) 0.0396(4) Uani d . 1 . . C
  H37A 0.4013 0.7913 -0.1177 0.048 Uiso calc R 1 . . H
  H37B 0.4855 0.6886 -0.1824 0.048 Uiso calc R 1 . . H
  C38 0.41236(16) 0.63067(15) -0.05174(10) 0.0341(4) Uani d . 1 . . C
  H38A 0.4221 0.5485 -0.0690 0.041 Uiso calc R 1 . . H
  H38B 0.4933 0.6414 -0.0290 0.041 Uiso calc R 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
  O1 0.0404(6) 0.0234(5) 0.0288(5) -0.0085(5) -0.0196(5) 0.0036(4)
  O2 0.0373(6) 0.0238(5) 0.0317(6) -0.0083(5) -0.0171(5) 0.0063(4)
  O3 0.0244(5) 0.0281(5) 0.0247(5) -0.0058(4) -0.0105(4) 0.0048(4)
  O4 0.0340(6) 0.0294(6) 0.0279(5) -0.0096(5) -0.0143(5) 0.0079(4)
  N1 0.0314(7) 0.0205(6) 0.0225(6) -0.0027(5) -0.0135(5) -0.0004(5)
  N2 0.0256(7) 0.0191(6) 0.0340(7) -0.0043(5) -0.0127(5) 0.0072(5)
  N3 0.0245(7) 0.0331(7) 0.0204(6) -0.0086(5) -0.0089(5) 0.0056(5)
  N4 0.0289(7) 0.0229(6) 0.0168(6) -0.0061(5) -0.0069(5) 0.0039(5)
  C1 0.0196(7) 0.0203(7) 0.0208(7) -0.0009(5) -0.0054(6) -0.0015(5)
  C2 0.0209(7) 0.0189(7) 0.0204(7) -0.0024(5) -0.0067(6) 0.0007(5)
  C3 0.0210(7) 0.0169(7) 0.0195(7) -0.0048(5) -0.0053(5) 0.0013(5)
  C4 0.0217(7) 0.0197(7) 0.0158(6) -0.0036(5) -0.0039(5) 0.0011(5)
  C5 0.0217(7) 0.0205(7) 0.0172(6) -0.0012(6) -0.0051(5) -0.0009(5)
  C6 0.0208(7) 0.0244(7) 0.0150(6) -0.0022(6) -0.0031(5) -0.0004(5)
  C7 0.0214(7) 0.0212(7) 0.0180(7) -0.0003(6) -0.0049(6) 0.0003(5)
  C8 0.0228(7) 0.0182(7) 0.0224(7) -0.0040(6) -0.0033(6) -0.0008(5)
  C9 0.0253(8) 0.0275(8) 0.0230(7) -0.0049(6) 0.0000(6) -0.0051(6)
  C10 0.0255(8) 0.0294(8) 0.0301(8) 0.0031(6) -0.0031(6) -0.0027(6)
  C11 0.0187(7) 0.0218(7) 0.0190(7) -0.0025(6) -0.0032(5) -0.0013(5)
  C12 0.0314(8) 0.0198(7) 0.0227(7) -0.0042(6) -0.0102(6) -0.0015(6)
  C13 0.0321(9) 0.0250(8) 0.0439(9) -0.0027(7) -0.0103(7) -0.0057(7)
  C14 0.0411(10) 0.0248(8) 0.0470(10) -0.0011(7) -0.0085(8) -0.0107(7)
  C15 0.0528(11) 0.0222(8) 0.0428(10) -0.0104(7) -0.0192(8) 0.0002(7)
  C16 0.0361(9) 0.0336(9) 0.0397(9) -0.0130(7) -0.0077(7) -0.0033(7)
  C17 0.0331(9) 0.0309(8) 0.0284(8) -0.0067(7) -0.0055(7) -0.0047(6)
  C18 0.0232(7) 0.0207(7) 0.0148(6) -0.0015(6) -0.0028(5) -0.0006(5)
  C19 0.0227(7) 0.0189(7) 0.0258(7) -0.0033(6) -0.0081(6) 0.0064(6)
  C20 0.0374(9) 0.0261(8) 0.0220(7) 0.0024(7) -0.0050(6) 0.0011(6)
  C21 0.0352(9) 0.0264(8) 0.0344(8) 0.0066(7) -0.0020(7) 0.0044(7)
  C22 0.0382(10) 0.0339(9) 0.0522(11) -0.0028(7) -0.0240(8) 0.0164(8)
  C23 0.0589(11) 0.0354(9) 0.0273(8) -0.0039(8) -0.0226(8) 0.0057(7)
  C24 0.0410(9) 0.0248(8) 0.0213(7) -0.0020(7) -0.0071(7) 0.0006(6)
  C25 0.0208(7) 0.0229(7) 0.0153(6) -0.0022(6) -0.0029(5) -0.0027(5)
  C26 0.0307(8) 0.0416(9) 0.0267(8) -0.0173(7) -0.0118(7) 0.0101(7)
  C27 0.0486(11) 0.0472(11) 0.0447(10) -0.0254(9) -0.0072(8) -0.0071(8)
  C28 0.0569(13) 0.0299(10) 0.0952(17) -0.0139(9) -0.0306(12) 0.0101(10)
  C29 0.0608(13) 0.0714(14) 0.0543(12) -0.0304(11) -0.0254(11) 0.0356(11)
  C30 0.0386(10) 0.0752(14) 0.0286(9) -0.0247(9) -0.0038(7) 0.0053(9)
  C31 0.0250(8) 0.0467(10) 0.0451(10) -0.0119(7) -0.0049(7) 0.0021(8)
  C32 0.0215(7) 0.0207(7) 0.0190(7) -0.0001(6) -0.0035(6) 0.0011(5)
  C33 0.0275(8) 0.0201(7) 0.0150(6) -0.0009(6) -0.0048(6) 0.0031(5)
  C34 0.0281(8) 0.0594(11) 0.0224(8) -0.0087(8) -0.0067(7) 0.0107(7)
  C35 0.0335(10) 0.0823(15) 0.0345(9) -0.0053(9) -0.0149(8) 0.0222(9)
  C36 0.0517(11) 0.0560(11) 0.0196(8) -0.0109(9) -0.0107(7) 0.0109(7)
  C37 0.0350(9) 0.0546(11) 0.0240(8) -0.0044(8) 0.0005(7) 0.0127(8)
  C38 0.0256(8) 0.0460(10) 0.0261(8) 0.0015(7) -0.0031(6) 0.0093(7)
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 C11 . 1.2401(16) ?
  O2 C18 . 1.2363(17) ?
  O3 C25 . 1.2389(16) ?
  O4 C32 . 1.2384(17) ?
  N1 C11 . 1.3219(18) ?
  N1 C12 . 1.4625(17) ?
  N1 H01 . 0.900(18) ?
  N2 C18 . 1.3233(18) ?
  N2 C19 . 1.4635(17) ?
  N2 H02 . 0.895(18) ?
  N3 C25 . 1.3317(18) ?
  N3 C26 . 1.4657(19) ?
  N3 H03 . 0.927(17) ?
  N4 C32 . 1.3275(17) ?
  N4 C33 . 1.4622(17) ?
  N4 H04 . 0.953(19) ?
  C1 C11 . 1.4988(18) ?
  C1 C2 . 1.5259(19) y
  C1 C7 . 1.5543(19) y
  C1 C5 . 1.5572(18) y
  C2 C3 . 1.4788(18) y
  C2 C7 . 1.5175(19) y
  C2 H2 . 1.0000 ?
  C3 C8 . 1.3343(19) y
  C3 C4 . 1.4791(19) y
  C4 C5 . 1.5268(18) y
  C4 C6 . 1.5298(18) y
  C4 H4 . 1.0000 ?
  C5 C18 . 1.5004(18) ?
  C5 C6 . 1.5545(19) y
  C6 C25 . 1.4978(19) ?
  C6 C7 . 1.5509(18) ?
  C7 C32 . 1.4982(18) ?
  C8 C10 . 1.5008(19) ?
  C8 C9 . 1.5014(19) ?
  C9 H9A . 0.9800 ?
  C9 H9B . 0.9800 ?
  C9 H9C . 0.9800 ?
  C10 H10A . 0.9800 ?
  C10 H10B . 0.9800 ?
  C10 H10C . 0.9800 ?
  C12 C17 . 1.518(2) ?
  C12 C13 . 1.524(2) ?
  C12 H12 . 1.0000 ?
  C13 C14 . 1.525(2) ?
  C13 H13A . 0.9900 ?
  C13 H13B . 0.9900 ?
  C14 C15 . 1.519(2) ?
  C14 H14A . 0.9900 ?
  C14 H14B . 0.9900 ?
  C15 C16 . 1.516(2) ?
  C15 H15A . 0.9900 ?
  C15 H15B . 0.9900 ?
  C16 C17 . 1.527(2) ?
  C16 H16A . 0.9900 ?
  C16 H16B . 0.9900 ?
  C17 H17A . 0.9900 ?
  C17 H17B . 0.9900 ?
  C19 C24 . 1.516(2) ?
  C19 C20 . 1.521(2) ?
  C19 H19 . 1.0000 ?
  C20 C21 . 1.524(2) ?
  C20 H20A . 0.9900 ?
  C20 H20B . 0.9900 ?
  C21 C22 . 1.508(2) ?
  C21 H21A . 0.9900 ?
  C21 H21B . 0.9900 ?
  C22 C23 . 1.512(2) ?
  C22 H22A . 0.9900 ?
  C22 H22B . 0.9900 ?
  C23 C24 . 1.524(2) ?
  C23 H23A . 0.9900 ?
  C23 H23B . 0.9900 ?
  C24 H24A . 0.9900 ?
  C24 H24B . 0.9900 ?
  C26 C31 . 1.519(2) ?
  C26 C27 . 1.530(2) ?
  C26 H26 . 1.0000 ?
  C27 C28 . 1.522(3) ?
  C27 H27A . 0.9900 ?
  C27 H27B . 0.9900 ?
  C28 C29 . 1.529(3) ?
  C28 H28A . 0.9900 ?
  C28 H28B . 0.9900 ?
  C29 C30 . 1.500(3) ?
  C29 H29A . 0.9900 ?
  C29 H29B . 0.9900 ?
  C30 C31 . 1.514(2) ?
  C30 H30A . 0.9900 ?
  C30 H30B . 0.9900 ?
  C31 H31A . 0.9900 ?
  C31 H31B . 0.9900 ?
  C33 C34 . 1.507(2) ?
  C33 C38 . 1.512(2) ?
  C33 H33 . 1.0000 ?
  C34 C35 . 1.519(2) ?
  C34 H34A . 0.9900 ?
  C34 H34B . 0.9900 ?
  C35 C36 . 1.512(3) ?
  C35 H35A . 0.9900 ?
  C35 H35B . 0.9900 ?
  C36 C37 . 1.508(2) ?
  C36 H36A . 0.9900 ?
  C36 H36B . 0.9900 ?
  C37 C38 . 1.527(2) ?
  C37 H37A . 0.9900 ?
  C37 H37B . 0.9900 ?
  C38 H38A . 0.9900 ?
  C38 H38B . 0.9900 ?
_cod_database_code 2202321