#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202324.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_2202324
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1103
_journal_page_last  o1105
_publ_section_title
;
 A tetrakis(tertiary amide) derivative of quadricyclane:
 3-Isopropylidene-tetracyclo[3.2.0.0^2,7^.0^4,6^]heptan-1,5,6,7-
 tetracarboxylic acid tetrakis(diethylamide)
;
loop_
_publ_author_name
  'Winkler, Torsten'
  'Herges, Rainer'
  'Jones, Peter G.'
  'Dix, Ina'
_chemical_formula_sum  'C30 H48 N4 O4'
_chemical_formula_weight  528.72
_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  10.8375(8)
_cell_length_b  11.6922(8)
_cell_length_c  13.7337(10)
_cell_angle_alpha  109.065(3)
_cell_angle_beta  101.073(3)
_cell_angle_gamma  106.800(3)
_cell_volume  1493.59(19)
_cell_formula_units_Z  2
_cell_measurement_temperature  133(2)
_exptl_crystal_density_diffrn  1.176
_diffrn_ambient_temperature  133(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 0.20249(9) 0.78494(9) 0.40800(7) 0.0303(2) Uani d . 1 A . O
  O2 0.38325(9) 0.38040(8) 0.24123(8) 0.0325(2) Uani d . 1 . . O
  O3 0.30457(9) 0.50436(9) 0.04316(7) 0.0332(2) Uani d . 1 A . O
  O4 0.44982(9) 1.01521(8) 0.34527(7) 0.0287(2) Uani d . 1 . . O
  N1 0.29341(10) 0.70016(10) 0.51542(8) 0.0240(2) Uani d . 1 A . N
  N2 0.18476(11) 0.40507(10) 0.23941(10) 0.0357(3) Uani d D 1 . . N
  N3 0.46959(11) 0.68472(10) 0.05547(8) 0.0277(2) Uani d . 1 A . N
  N4 0.27657(11) 0.87143(10) 0.19391(9) 0.0283(2) Uani d . 1 . . N
  C1 0.38238(11) 0.72177(11) 0.36999(9) 0.0197(2) Uani d . 1 A . C
  C2 0.52392(11) 0.82734(11) 0.40662(9) 0.0193(2) Uani d . 1 A . C
  H2 0.5513 0.9128 0.4696 0.023 Uiso calc R 1 . . H
  C3 0.62373(11) 0.76636(11) 0.38673(9) 0.0202(2) Uani d . 1 . . C
  C4 0.53939(11) 0.64552(11) 0.28906(9) 0.0208(2) Uani d . 1 A . C
  H4 0.5798 0.5823 0.2547 0.025 Uiso calc R 1 . . H
  C5 0.39286(11) 0.59675(11) 0.28954(9) 0.0203(2) Uani d . 1 . . C
  C6 0.43074(11) 0.67008(11) 0.21909(9) 0.0203(2) Uani d . 1 A . C
  C7 0.42035(11) 0.79429(11) 0.29908(9) 0.0193(2) Uani d . 1 . . C
  C8 0.75585(12) 0.80992(12) 0.44102(10) 0.0241(2) Uani d . 1 . . C
  C9 0.82600(13) 0.93387(13) 0.54204(11) 0.0338(3) Uani d . 1 . . C
  H9A 0.7589 0.9692 0.5633 0.041 Uiso calc R 1 . . H
  H9B 0.8933 0.9979 0.5282 0.041 Uiso calc R 1 . . H
  H9C 0.8716 0.9156 0.6007 0.041 Uiso calc R 1 . . H
  C10 0.84586(12) 0.73922(13) 0.40492(12) 0.0321(3) Uani d . 1 . . C
  H10A 0.7916 0.6585 0.3399 0.039 Uiso calc R 1 . . H
  H10B 0.8870 0.7177 0.4631 0.039 Uiso calc R 1 . . H
  H10C 0.9176 0.7954 0.3882 0.039 Uiso calc R 1 . . H
  C11 0.28542(11) 0.73851(11) 0.43291(9) 0.0217(2) Uani d . 1 . . C
  C12 0.19938(13) 0.71676(13) 0.57739(11) 0.0324(3) Uani d . 1 . . C
  H12A 0.1886 0.6545 0.6126 0.039 Uiso calc R 1 A . H
  H12B 0.1093 0.6946 0.5266 0.039 Uiso calc R 1 . . H
  C13 0.24526(16) 0.85370(16) 0.66354(13) 0.0464(4) Uani d . 1 A . C
  H13A 0.3344 0.8766 0.7142 0.056 Uiso calc R 1 . . H
  H13B 0.1793 0.8576 0.7032 0.056 Uiso calc R 1 . . H
  H13C 0.2517 0.9156 0.6290 0.056 Uiso calc R 1 . . H
  C14 0.40144(13) 0.66079(12) 0.55725(10) 0.0282(3) Uani d . 1 . . C
  H14A 0.4434 0.7140 0.6364 0.034 Uiso calc R 1 A . H
  H14B 0.4726 0.6789 0.5225 0.034 Uiso calc R 1 . . H
  C15 0.35012(15) 0.51725(14) 0.53655(13) 0.0396(3) Uani d . 1 A . C
  H15A 0.2771 0.4980 0.5683 0.048 Uiso calc R 1 . . H
  H15B 0.4248 0.4969 0.5698 0.048 Uiso calc R 1 . . H
  H15C 0.3153 0.4639 0.4581 0.048 Uiso calc R 1 . . H
  C16 0.31929(12) 0.45210(12) 0.25344(10) 0.0251(3) Uani d . 1 A . C
  C17 0.1234(2) 0.26610(19) 0.2222(2) 0.0314(6) Uani d PD 0.756(5) A 1 C
  H17A 0.0568 0.2565 0.2622 0.038 Uiso calc PR 0.756(5) A 1 H
  H17B 0.1951 0.2381 0.2509 0.038 Uiso calc PR 0.756(5) A 1 H
  C18 0.0537(3) 0.1813(2) 0.1035(2) 0.0570(8) Uani d PD 0.756(5) A 1 C
  H18A -0.0181 0.2084 0.0756 0.068 Uiso calc PR 0.756(5) A 1 H
  H18B 0.0137 0.0898 0.0932 0.068 Uiso calc PR 0.756(5) A 1 H
  H18C 0.1200 0.1902 0.0642 0.068 Uiso calc PR 0.756(5) A 1 H
  C17' 0.1000(6) 0.2618(6) 0.1660(6) 0.0297(17) Uani d PD 0.244(5) A 2 C
  H17C 0.0082 0.2490 0.1242 0.036 Uiso calc PR 0.244(5) A 2 H
  H17D 0.1455 0.2233 0.1156 0.036 Uiso calc PR 0.244(5) A 2 H
  C18' 0.0955(6) 0.2072(6) 0.2532(6) 0.045(2) Uani d PD 0.244(5) A 2 C
  H18D 0.1878 0.2200 0.2916 0.054 Uiso calc PR 0.244(5) A 2 H
  H18E 0.0388 0.1136 0.2188 0.054 Uiso calc PR 0.244(5) A 2 H
  H18F 0.0570 0.2530 0.3049 0.054 Uiso calc PR 0.244(5) A 2 H
  C19 0.09622(13) 0.47470(13) 0.22217(12) 0.0332(3) Uani d . 1 A . C
  H19A 0.0434 0.4360 0.1441 0.040 Uiso calc R 1 . . H
  H19B 0.1529 0.5672 0.2422 0.040 Uiso calc R 1 . . H
  C20 -0.00118(14) 0.46942(15) 0.28792(14) 0.0418(4) Uani d . 1 . . C
  H20A -0.0678 0.3798 0.2599 0.050 Uiso calc R 1 A . H
  H20B -0.0485 0.5280 0.2821 0.050 Uiso calc R 1 . . H
  H20C 0.0497 0.4971 0.3642 0.050 Uiso calc R 1 . . H
  C21 0.39500(12) 0.61257(12) 0.09818(10) 0.0239(2) Uani d . 1 . . C
  C22 0.58444(13) 0.80895(12) 0.12003(11) 0.0295(3) Uani d . 1 . . C
  H22A 0.5748 0.8477 0.1925 0.035 Uiso calc R 1 A . H
  H22B 0.5817 0.8699 0.0845 0.035 Uiso calc R 1 . . H
  C23 0.72126(14) 0.79567(15) 0.13429(13) 0.0435(4) Uani d . 1 A . C
  H23A 0.7280 0.7418 0.1752 0.052 Uiso calc R 1 . . H
  H23B 0.7940 0.8825 0.1741 0.052 Uiso calc R 1 . . H
  H23C 0.7302 0.7542 0.0628 0.052 Uiso calc R 1 . . H
  C24 0.44416(15) 0.63029(15) -0.06204(10) 0.0368(3) Uani d . 1 . . C
  H24A 0.3992 0.5339 -0.0915 0.044 Uiso calc R 1 A . H
  H24B 0.5320 0.6512 -0.0768 0.044 Uiso calc R 1 . . H
  C25 0.35664(19) 0.6826(2) -0.11906(13) 0.0590(5) Uani d . 1 A . C
  H25A 0.2680 0.6587 -0.1074 0.071 Uiso calc R 1 . . H
  H25B 0.3442 0.6452 -0.1970 0.071 Uiso calc R 1 . . H
  H25C 0.4006 0.7781 -0.0900 0.071 Uiso calc R 1 . . H
  C26 0.38140(11) 0.90130(11) 0.28165(9) 0.0215(2) Uani d . 1 A . C
  C27 0.25626(15) 0.98161(14) 0.17382(12) 0.0374(3) Uani d . 1 . . C
  H27A 0.2801 1.0556 0.2443 0.045 Uiso calc R 1 . . H
  H27B 0.1591 0.9553 0.1347 0.045 Uiso calc R 1 . . H
  C28 0.3401(2) 1.02584(19) 0.10872(17) 0.0594(5) Uani d . 1 . . C
  H28A 0.4361 1.0481 0.1453 0.071 Uiso calc R 1 . . H
  H28B 0.3280 1.1030 0.1018 0.071 Uiso calc R 1 . . H
  H28C 0.3112 0.9554 0.0363 0.071 Uiso calc R 1 . . H
  C29 0.17208(13) 0.74177(13) 0.12725(11) 0.0316(3) Uani d . 1 . . C
  H29A 0.2042 0.6758 0.1412 0.038 Uiso calc R 1 . . H
  H29B 0.1583 0.7251 0.0497 0.038 Uiso calc R 1 . . H
  C30 0.03673(14) 0.72489(16) 0.14871(13) 0.0438(4) Uani d . 1 . . C
  H30A 0.0491 0.7394 0.2250 0.053 Uiso calc R 1 . . H
  H30B -0.0290 0.6360 0.1018 0.053 Uiso calc R 1 . . H
  H30C 0.0029 0.7883 0.1332 0.053 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 0.0295(5) 0.0371(5) 0.0346(5) 0.0207(4) 0.0162(4) 0.0164(4)
  O2 0.0338(5) 0.0222(4) 0.0448(6) 0.0137(4) 0.0181(4) 0.0116(4)
  O3 0.0308(5) 0.0300(5) 0.0254(5) 0.0066(4) 0.0063(4) 0.0011(4)
  O4 0.0362(5) 0.0218(4) 0.0280(5) 0.0129(4) 0.0098(4) 0.0086(4)
  N1 0.0236(5) 0.0267(5) 0.0257(5) 0.0103(4) 0.0139(4) 0.0114(4)
  N2 0.0255(6) 0.0203(5) 0.0564(8) 0.0063(5) 0.0181(5) 0.0089(5)
  N3 0.0332(6) 0.0299(6) 0.0202(5) 0.0133(5) 0.0118(4) 0.0073(4)
  N4 0.0302(5) 0.0302(6) 0.0284(6) 0.0172(5) 0.0071(4) 0.0127(5)
  C1 0.0204(5) 0.0194(5) 0.0212(6) 0.0088(5) 0.0090(4) 0.0078(5)
  C2 0.0198(5) 0.0188(5) 0.0186(5) 0.0074(4) 0.0070(4) 0.0061(4)
  C3 0.0222(5) 0.0205(6) 0.0216(6) 0.0093(5) 0.0101(5) 0.0100(5)
  C4 0.0209(5) 0.0207(6) 0.0233(6) 0.0100(5) 0.0105(5) 0.0083(5)
  C5 0.0201(5) 0.0199(6) 0.0223(6) 0.0094(5) 0.0100(4) 0.0070(5)
  C6 0.0207(5) 0.0206(6) 0.0196(6) 0.0088(5) 0.0080(4) 0.0062(5)
  C7 0.0203(5) 0.0202(6) 0.0182(5) 0.0096(5) 0.0084(4) 0.0058(4)
  C8 0.0212(6) 0.0230(6) 0.0295(6) 0.0087(5) 0.0093(5) 0.0114(5)
  C9 0.0235(6) 0.0299(7) 0.0372(8) 0.0081(6) 0.0042(5) 0.0056(6)
  C10 0.0211(6) 0.0294(7) 0.0462(8) 0.0109(5) 0.0122(6) 0.0136(6)
  C11 0.0207(5) 0.0201(6) 0.0227(6) 0.0075(5) 0.0094(5) 0.0056(5)
  C12 0.0325(7) 0.0362(7) 0.0333(7) 0.0115(6) 0.0218(6) 0.0146(6)
  C13 0.0474(9) 0.0469(9) 0.0417(9) 0.0149(7) 0.0294(7) 0.0080(7)
  C14 0.0290(6) 0.0321(7) 0.0287(7) 0.0130(5) 0.0112(5) 0.0163(6)
  C15 0.0463(8) 0.0360(8) 0.0430(8) 0.0175(7) 0.0140(7) 0.0222(7)
  C16 0.0272(6) 0.0214(6) 0.0270(6) 0.0091(5) 0.0129(5) 0.0078(5)
  C17 0.0264(10) 0.0233(11) 0.0387(14) 0.0045(8) 0.0067(10) 0.0121(11)
  C18 0.0614(15) 0.0258(13) 0.0554(16) 0.0100(11) -0.0108(12) 0.0048(13)
  C17' 0.023(3) 0.022(4) 0.027(4) 0.004(3) 0.006(3) -0.004(4)
  C18' 0.040(4) 0.030(3) 0.080(5) 0.015(3) 0.034(3) 0.031(4)
  C19 0.0233(6) 0.0266(7) 0.0400(8) 0.0064(5) 0.0105(6) 0.0044(6)
  C20 0.0262(7) 0.0344(8) 0.0574(10) 0.0082(6) 0.0191(7) 0.0092(7)
  C21 0.0235(6) 0.0266(6) 0.0224(6) 0.0132(5) 0.0089(5) 0.0067(5)
  C22 0.0343(7) 0.0285(7) 0.0290(7) 0.0119(6) 0.0178(6) 0.0112(5)
  C23 0.0346(8) 0.0412(9) 0.0519(9) 0.0125(7) 0.0204(7) 0.0133(7)
  C24 0.0472(8) 0.0427(8) 0.0221(7) 0.0187(7) 0.0171(6) 0.0102(6)
  C25 0.0594(10) 0.0945(14) 0.0290(8) 0.0404(11) 0.0124(8) 0.0234(9)
  C26 0.0241(6) 0.0250(6) 0.0219(6) 0.0135(5) 0.0125(5) 0.0105(5)
  C27 0.0441(8) 0.0415(8) 0.0384(8) 0.0278(7) 0.0112(6) 0.0213(7)
  C28 0.0774(12) 0.0665(12) 0.0738(13) 0.0454(11) 0.0397(10) 0.0513(11)
  C29 0.0277(6) 0.0370(7) 0.0269(7) 0.0153(6) 0.0043(5) 0.0089(6)
  C30 0.0287(7) 0.0539(10) 0.0493(9) 0.0199(7) 0.0090(6) 0.0198(8)
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 . 1.2267(14) ?
  O2 C16 . 1.2248(14) ?
  O3 C21 . 1.2274(15) ?
  O4 C26 . 1.2277(14) ?
  N1 C11 . 1.3451(15) ?
  N1 C14 . 1.4624(15) ?
  N1 C12 . 1.4629(15) ?
  N2 C16 . 1.3508(16) ?
  N2 C19 . 1.4593(17) ?
  N2 C17 . 1.484(2) ?
  N2 C17' . 1.522(6) ?
  N3 C21 . 1.3493(15) ?
  N3 C22 . 1.4611(16) ?
  N3 C24 . 1.4636(16) ?
  N4 C26 . 1.3544(15) ?
  N4 C29 . 1.4565(17) ?
  N4 C27 . 1.4686(16) ?
  C1 C11 . 1.4987(15) ?
  C1 C7 . 1.5259(15) y
  C1 C2 . 1.5274(15) y
  C1 C5 . 1.5683(16) y
  C2 C3 . 1.4782(15) y
  C2 C7 . 1.5264(15) y
  C2 H2 . 1.0000 ?
  C3 C8 . 1.3363(16) y
  C3 C4 . 1.4749(16) y
  C4 C5 . 1.5264(15) y
  C4 C6 . 1.5276(15) y
  C4 H4 . 1.0000 ?
  C5 C16 . 1.5042(16) ?
  C5 C6 . 1.5267(15) y
  C6 C21 . 1.4941(16) ?
  C6 C7 . 1.5584(15) ?
  C7 C26 . 1.5044(15) ?
  C8 C9 . 1.4992(18) ?
  C8 C10 . 1.5050(17) ?
  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 C13 . 1.512(2) ?
  C12 H12A . 0.9900 ?
  C12 H12B . 0.9900 ?
  C13 H13A . 0.9800 ?
  C13 H13B . 0.9800 ?
  C13 H13C . 0.9800 ?
  C14 C15 . 1.5149(19) ?
  C14 H14A . 0.9900 ?
  C14 H14B . 0.9900 ?
  C15 H15A . 0.9800 ?
  C15 H15B . 0.9800 ?
  C15 H15C . 0.9800 ?
  C17 C18 . 1.500(3) ?
  C17 H17A . 0.9900 ?
  C17 H17B . 0.9900 ?
  C18 H18A . 0.9800 ?
  C18 H18B . 0.9800 ?
  C18 H18C . 0.9800 ?
  C17' C18' . 1.532(9) ?
  C17' H17C . 0.9900 ?
  C17' H17D . 0.9900 ?
  C18' H18D . 0.9800 ?
  C18' H18E . 0.9800 ?
  C18' H18F . 0.9800 ?
  C19 C20 . 1.5160(19) ?
  C19 H19A . 0.9900 ?
  C19 H19B . 0.9900 ?
  C20 H20A . 0.9800 ?
  C20 H20B . 0.9800 ?
  C20 H20C . 0.9800 ?
  C22 C23 . 1.5175(19) ?
  C22 H22A . 0.9900 ?
  C22 H22B . 0.9900 ?
  C23 H23A . 0.9800 ?
  C23 H23B . 0.9800 ?
  C23 H23C . 0.9800 ?
  C24 C25 . 1.500(2) ?
  C24 H24A . 0.9900 ?
  C24 H24B . 0.9900 ?
  C25 H25A . 0.9800 ?
  C25 H25B . 0.9800 ?
  C25 H25C . 0.9800 ?
  C27 C28 . 1.495(2) ?
  C27 H27A . 0.9900 ?
  C27 H27B . 0.9900 ?
  C28 H28A . 0.9800 ?
  C28 H28B . 0.9800 ?
  C28 H28C . 0.9800 ?
  C29 C30 . 1.5212(19) ?
  C29 H29A . 0.9900 ?
  C29 H29B . 0.9900 ?
  C30 H30A . 0.9800 ?
  C30 H30B . 0.9800 ?
  C30 H30C . 0.9800 ?