#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202317.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_2202317
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o997
_journal_page_last  o999
_publ_section_title
;
A tetrakis(secondary amide) derivative of quadricyclane:
N,N',N'',N'''-3-isopropylidenetetracyclo[3.2.0.0^2,7^.0^4,5^]heptane-
1,5,6,7-tetracarboxamide
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Winkler, Torsten'
  'Herges, Rainer'
  'Jones, Peter G.'
  'Dix, Ina'
_chemical_formula_moiety  'C26 H40 N4 O4'
_chemical_formula_sum  'C26 H40 N4 O4'
_chemical_formula_iupac  'C26 H40 N4 O4'
_chemical_formula_weight  472.62
_symmetry_cell_setting  monoclinic
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  13.3354(18)
_cell_length_b  12.1987(16)
_cell_length_c  16.981(2)
_cell_angle_alpha  90.00
_cell_angle_beta  104.454(4)
_cell_angle_gamma  90.00
_cell_volume  2674.9(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  143(2)
_exptl_crystal_density_diffrn  1.174
_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 0.40156(7) 0.71048(9) 0.33737(6) 0.0340(2) Uani d . 1 . . O
  O2 0.11914(7) 0.47992(8) 0.25825(6) 0.0306(2) Uani d . 1 . . O
  O3 0.11756(7) 0.43277(8) 0.52907(5) 0.0283(2) Uani d . 1 . . O
  O4 0.40345(8) 0.65406(9) 0.60557(6) 0.0370(3) Uani d . 1 . . O
  N1 0.29696(9) 0.58874(10) 0.25556(7) 0.0293(3) Uani d . 1 . . N
  H01 0.2397(13) 0.5487(14) 0.2502(10) 0.041(4) Uiso d . 1 . . H
  N2 0.06824(8) 0.40171(9) 0.36231(7) 0.0252(2) Uani d . 1 . . N
  H02 0.0734(12) 0.4042(13) 0.4150(11) 0.040(5) Uiso d . 1 . . H
  N3 0.25291(9) 0.51234(10) 0.61771(7) 0.0305(3) Uani d . 1 . . N
  H03 0.3059(13) 0.5612(14) 0.6196(10) 0.043(5) Uiso d . 1 . . H
  N4 0.46474(8) 0.72064(10) 0.50320(7) 0.0279(3) Uani d . 1 . . N
  H04 0.4506(13) 0.7248(14) 0.4494(11) 0.044(5) Uiso d . 1 . . H
  C1 0.25436(10) 0.64815(10) 0.37850(8) 0.0247(3) Uani d . 1 . . C
  C2 0.23236(10) 0.75299(10) 0.41968(7) 0.0232(3) Uani d . 1 . . C
  H2 0.2698 0.8224 0.4139 0.028 Uiso calc R 1 . . H
  C3 0.12181(10) 0.75539(10) 0.42154(7) 0.0222(3) Uani d . 1 . . C
  C4 0.10115(10) 0.63777(10) 0.43070(7) 0.0219(3) Uani d . 1 . . C
  H4 0.0310 0.6123 0.4340 0.026 Uiso calc R 1 . . H
  C5 0.16563(10) 0.56943(11) 0.38656(8) 0.0243(3) Uani d . 1 . . C
  C6 0.19863(10) 0.58233(11) 0.48110(8) 0.0246(3) Uani d . 1 . . C
  C7 0.28756(10) 0.66050(11) 0.47355(8) 0.0253(3) Uani d . 1 . . C
  C8 0.05700(10) 0.84005(11) 0.41577(8) 0.0250(3) Uani d . 1 . . C
  C9 -0.05506(11) 0.82621(12) 0.41536(9) 0.0306(3) Uani d . 1 . . C
  H9A -0.0700 0.7483 0.4206 0.037 Uiso calc R 1 . . H
  H9B -0.0986 0.8545 0.3642 0.037 Uiso calc R 1 . . H
  H9C -0.0696 0.8668 0.4611 0.037 Uiso calc R 1 . . H
  C10 0.09022(12) 0.95642(11) 0.40749(9) 0.0331(3) Uani d . 1 . . C
  H10A 0.1638 0.9578 0.4077 0.040 Uiso calc R 1 . . H
  H10B 0.0794 1.0000 0.4531 0.040 Uiso calc R 1 . . H
  H10C 0.0492 0.9873 0.3563 0.040 Uiso calc R 1 . . H
  C11 0.32395(10) 0.65085(11) 0.32153(8) 0.0245(3) Uani d . 1 . . C
  C12 0.35941(11) 0.57854(13) 0.19609(8) 0.0340(3) Uani d . 1 . . C
  H12 0.4100 0.6405 0.2041 0.041 Uiso calc R 1 . . H
  C13 0.28954(14) 0.58536(16) 0.11088(9) 0.0470(4) Uani d . 1 . . C
  H13A 0.2385 0.5259 0.1028 0.056 Uiso calc R 1 . . H
  H13B 0.3313 0.5785 0.0711 0.056 Uiso calc R 1 . . H
  H13C 0.2536 0.6561 0.1036 0.056 Uiso calc R 1 . . H
  C14 0.41852(15) 0.47190(18) 0.20974(11) 0.0578(5) Uani d . 1 . . C
  H14A 0.4632 0.4703 0.2651 0.069 Uiso calc R 1 . . H
  H14B 0.4611 0.4655 0.1706 0.069 Uiso calc R 1 . . H
  H14C 0.3696 0.4106 0.2024 0.069 Uiso calc R 1 . . H
  C15 0.11694(9) 0.47874(10) 0.33112(8) 0.0231(3) Uani d . 1 . . C
  C16 0.01322(10) 0.31093(11) 0.31338(8) 0.0261(3) Uani d . 1 . . C
  H16 -0.0248 0.3405 0.2592 0.031 Uiso calc R 1 . . H
  C17 -0.06524(12) 0.26435(13) 0.35519(10) 0.0371(4) Uani d . 1 . . C
  H17A -0.0294 0.2373 0.4092 0.045 Uiso calc R 1 . . H
  H17B -0.1026 0.2038 0.3227 0.045 Uiso calc R 1 . . H
  H17C -0.1144 0.3218 0.3607 0.045 Uiso calc R 1 . . H
  C18 0.08837(12) 0.22424(12) 0.29976(11) 0.0393(4) Uani d . 1 . . C
  H18A 0.1392 0.2577 0.2742 0.047 Uiso calc R 1 . . H
  H18B 0.0503 0.1668 0.2641 0.047 Uiso calc R 1 . . H
  H18C 0.1242 0.1920 0.3521 0.047 Uiso calc R 1 . . H
  C19 0.18784(10) 0.50196(11) 0.54487(8) 0.0240(3) Uani d . 1 . . C
  C20 0.24770(11) 0.44230(13) 0.68687(8) 0.0347(3) Uani d . 1 . . C
  H20 0.1742 0.4183 0.6796 0.042 Uiso calc R 1 . . H
  C21 0.27845(15) 0.51000(17) 0.76390(10) 0.0526(5) Uani d . 1 . . C
  H21A 0.3485 0.5391 0.7699 0.063 Uiso calc R 1 . . H
  H21B 0.2771 0.4638 0.8109 0.063 Uiso calc R 1 . . H
  H21C 0.2297 0.5709 0.7607 0.063 Uiso calc R 1 . . H
  C22 0.31397(14) 0.34113(15) 0.68934(11) 0.0479(4) Uani d . 1 . . C
  H22A 0.2892 0.2993 0.6389 0.057 Uiso calc R 1 . . H
  H22B 0.3095 0.2955 0.7359 0.057 Uiso calc R 1 . . H
  H22C 0.3861 0.3630 0.6948 0.057 Uiso calc R 1 . . H
  C23 0.39074(10) 0.67671(11) 0.53276(8) 0.0258(3) Uani d . 1 . . C
  C24 0.56923(10) 0.73967(13) 0.55390(9) 0.0333(3) Uani d . 1 . . C
  H24 0.5642 0.7614 0.6096 0.040 Uiso calc R 1 . . H
  C25 0.61711(13) 0.83351(15) 0.51756(11) 0.0489(4) Uani d . 1 . . C
  H25A 0.6190 0.8149 0.4618 0.059 Uiso calc R 1 . . H
  H25B 0.6877 0.8465 0.5504 0.059 Uiso calc R 1 . . H
  H25C 0.5755 0.8999 0.5170 0.059 Uiso calc R 1 . . H
  C26 0.63320(13) 0.63621(16) 0.56064(13) 0.0581(5) Uani d . 1 . . C
  H26A 0.5998 0.5777 0.5844 0.070 Uiso calc R 1 . . H
  H26B 0.7026 0.6499 0.5955 0.070 Uiso calc R 1 . . H
  H26C 0.6387 0.6140 0.5064 0.070 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 0.0344(5) 0.0450(6) 0.0251(5) -0.0151(5) 0.0120(4) -0.0058(4)
  O2 0.0344(5) 0.0320(5) 0.0261(5) -0.0097(4) 0.0088(4) -0.0027(4)
  O3 0.0302(5) 0.0299(5) 0.0257(5) -0.0036(4) 0.0086(4) 0.0055(4)
  O4 0.0338(5) 0.0468(6) 0.0282(5) -0.0094(5) 0.0038(4) 0.0061(5)
  N1 0.0283(6) 0.0334(7) 0.0296(6) -0.0085(5) 0.0134(5) -0.0064(5)
  N2 0.0282(6) 0.0256(6) 0.0220(6) -0.0060(5) 0.0069(5) -0.0036(5)
  N3 0.0297(6) 0.0345(7) 0.0272(6) -0.0055(5) 0.0071(5) 0.0076(5)
  N4 0.0239(6) 0.0356(7) 0.0225(6) -0.0055(5) 0.0024(5) -0.0001(5)
  C1 0.0285(7) 0.0217(7) 0.0261(7) -0.0020(5) 0.0105(5) -0.0008(5)
  C2 0.0288(7) 0.0204(6) 0.0202(6) -0.0028(5) 0.0059(5) -0.0006(5)
  C3 0.0281(6) 0.0217(7) 0.0167(6) -0.0016(5) 0.0054(5) -0.0006(5)
  C4 0.0236(6) 0.0221(6) 0.0204(6) 0.0006(5) 0.0060(5) 0.0008(5)
  C5 0.0235(6) 0.0235(7) 0.0274(7) -0.0008(5) 0.0088(5) -0.0024(5)
  C6 0.0236(6) 0.0253(7) 0.0254(7) 0.0016(5) 0.0073(5) 0.0049(5)
  C7 0.0253(7) 0.0229(7) 0.0271(7) -0.0014(5) 0.0055(5) 0.0031(5)
  C8 0.0338(7) 0.0226(7) 0.0180(6) 0.0024(5) 0.0054(5) -0.0013(5)
  C9 0.0338(7) 0.0275(7) 0.0311(7) 0.0084(6) 0.0094(6) 0.0014(6)
  C10 0.0429(8) 0.0213(7) 0.0333(8) 0.0030(6) 0.0063(6) -0.0013(6)
  C11 0.0271(7) 0.0242(7) 0.0233(7) -0.0006(5) 0.0085(5) 0.0034(5)
  C12 0.0336(7) 0.0427(9) 0.0299(7) -0.0099(6) 0.0157(6) -0.0081(7)
  C13 0.0538(10) 0.0597(11) 0.0305(8) 0.0054(8) 0.0164(7) 0.0060(8)
  C14 0.0526(10) 0.0841(15) 0.0399(10) 0.0276(10) 0.0176(8) 0.0008(9)
  C15 0.0212(6) 0.0220(7) 0.0261(7) 0.0016(5) 0.0062(5) -0.0021(5)
  C16 0.0288(7) 0.0230(7) 0.0253(7) -0.0047(5) 0.0046(5) -0.0012(5)
  C17 0.0357(8) 0.0370(8) 0.0408(9) -0.0128(6) 0.0135(7) -0.0055(7)
  C18 0.0421(9) 0.0256(8) 0.0533(10) -0.0034(6) 0.0178(7) -0.0060(7)
  C19 0.0232(6) 0.0249(7) 0.0261(7) 0.0046(5) 0.0101(5) 0.0042(5)
  C20 0.0334(7) 0.0456(9) 0.0252(7) -0.0046(7) 0.0075(6) 0.0113(6)
  C21 0.0587(11) 0.0705(13) 0.0286(8) -0.0065(9) 0.0110(8) 0.0026(8)
  C22 0.0521(10) 0.0500(10) 0.0423(9) 0.0062(8) 0.0130(8) 0.0203(8)
  C23 0.0268(7) 0.0225(7) 0.0273(7) 0.0002(5) 0.0051(5) 0.0012(5)
  C24 0.0238(7) 0.0445(9) 0.0294(7) -0.0061(6) 0.0025(6) -0.0015(6)
  C25 0.0374(9) 0.0568(11) 0.0493(10) -0.0189(8) 0.0045(7) 0.0029(8)
  C26 0.0333(9) 0.0588(12) 0.0777(14) 0.0079(8) 0.0053(9) 0.0096(10)
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 . 1.2384(16) ?
  O2 C15 . 1.2451(16) ?
  O3 C19 . 1.2398(16) ?
  O4 C23 . 1.2364(16) ?
  N1 C11 . 1.3256(17) ?
  N1 C12 . 1.4659(17) ?
  N1 H01 . 0.892(17) ?
  N2 C15 . 1.3255(17) ?
  N2 C16 . 1.4666(17) ?
  N2 H02 . 0.881(17) ?
  N3 C19 . 1.3278(17) ?
  N3 C20 . 1.4679(18) ?
  N3 H03 . 0.919(18) ?
  N4 C23 . 1.3268(17) ?
  N4 C24 . 1.4622(17) ?
  N4 H04 . 0.888(18) ?
  C1 C11 . 1.4988(18) ?
  C1 C2 . 1.5209(18) y
  C1 C5 . 1.5563(17) y
  C1 C7 . 1.5707(18) y
  C2 C3 . 1.4828(18) y
  C2 C7 . 1.5217(18) y
  C2 H2 . 1.0000 ?
  C3 C8 . 1.3345(18) y
  C3 C4 . 1.4765(18) y
  C4 C5 . 1.5224(17) y
  C4 C6 . 1.5245(17) y
  C4 H4 . 1.0000 ?
  C5 C15 . 1.4922(18) ?
  C5 C6 . 1.5630(18) y
  C6 C19 . 1.4941(18) ?
  C6 C7 . 1.5517(17) ?
  C7 C23 . 1.5009(18) ?
  C8 C9 . 1.5021(19) ?
  C8 C10 . 1.5041(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 C14 . 1.509(2) ?
  C12 C13 . 1.515(2) ?
  C12 H12 . 1.0000 ?
  C13 H13A . 0.9800 ?
  C13 H13B . 0.9800 ?
  C13 H13C . 0.9800 ?
  C14 H14A . 0.9800 ?
  C14 H14B . 0.9800 ?
  C14 H14C . 0.9800 ?
  C16 C18 . 1.514(2) ?
  C16 C17 . 1.5141(19) ?
  C16 H16 . 1.0000 ?
  C17 H17A . 0.9800 ?
  C17 H17B . 0.9800 ?
  C17 H17C . 0.9800 ?
  C18 H18A . 0.9800 ?
  C18 H18B . 0.9800 ?
  C18 H18C . 0.9800 ?
  C20 C22 . 1.512(2) ?
  C20 C21 . 1.514(2) ?
  C20 H20 . 1.0000 ?
  C21 H21A . 0.9800 ?
  C21 H21B . 0.9800 ?
  C21 H21C . 0.9800 ?
  C22 H22A . 0.9800 ?
  C22 H22B . 0.9800 ?
  C22 H22C . 0.9800 ?
  C24 C26 . 1.512(2) ?
  C24 C25 . 1.515(2) ?
  C24 H24 . 1.0000 ?
  C25 H25A . 0.9800 ?
  C25 H25B . 0.9800 ?
  C25 H25C . 0.9800 ?
  C26 H26A . 0.9800 ?
  C26 H26B . 0.9800 ?
  C26 H26C . 0.9800 ?