#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013933.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_2013933
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o374
_journal_page_last  o376
_publ_section_title
;
Two stereoisomers of the rat toxicant norbormide
;
loop_
_publ_author_name
  'Steel, Peter J.'
  'Brimble, Margaret A.'
  'Hopkins, Brian'
  'Rennison, David'
_chemical_name_common
  'trans-endo-threo-norbormide ethyl acetate hemi-solvate'
_chemical_formula_moiety  'C33 H25 N3 O3, 0.5C4 H8 O2'
_chemical_formula_sum  'C35 H29 N3 O4'
_chemical_formula_iupac  'C33 H25 N3 O3, 0.5C4 H8 O2'
_chemical_formula_weight  555.61
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 2/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
_cell_length_a  17.999(3)
_cell_length_b  12.614(2)
_cell_length_c  13.063(2)
_cell_angle_alpha  90.00
_cell_angle_beta  110.834(2)
_cell_angle_gamma  90.00
_cell_volume  2771.9(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  173(2)
_exptl_crystal_density_diffrn  1.331
_diffrn_ambient_temperature  173(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
  C1 0.37122(18) 0.2113(3) 0.4608(3) 0.0270(9) Uani d . 1 . . C
  H1A 0.4123 0.2227 0.5351 0.032 Uiso calc R 1 . . H
  C2 0.37433(18) 0.1028(3) 0.4048(3) 0.0281(9) Uani d . 1 . . C
  H2A 0.3822 0.0423 0.4571 0.034 Uiso calc R 1 . . H
  C3 0.29164(19) 0.0976(3) 0.3114(3) 0.0295(9) Uani d . 1 . . C
  H3A 0.2621 0.0324 0.3181 0.035 Uiso calc R 1 . . H
  C4 0.24798(19) 0.2007(3) 0.3293(3) 0.0316(9) Uani d . 1 . . C
  H4A 0.1886 0.2008 0.2960 0.038 Uiso calc R 1 . . H
  C5 0.29116(19) 0.2944(3) 0.3005(3) 0.0262(9) Uani d . 1 . . C
  C6 0.36368(19) 0.2981(3) 0.3765(3) 0.0280(9) Uani d . 1 . . C
  H6A 0.4042 0.3469 0.3780 0.034 Uiso calc R 1 . . H
  C7 0.28429(19) 0.2064(3) 0.4547(3) 0.0259(9) Uani d . 1 . . C
  C8 0.25028(19) 0.2029(3) 0.5292(3) 0.0278(9) Uani d . 1 . . C
  C9 0.4327(2) 0.0994(3) 0.3473(3) 0.0299(9) Uani d . 1 . . C
  O2 0.50616(14) 0.10026(18) 0.38965(19) 0.0372(7) Uani d . 1 . . O
  N1 0.39228(17) 0.0969(2) 0.2364(3) 0.0313(8) Uani d D 1 . . N
  H1C 0.4223(18) 0.097(3) 0.192(2) 0.047 Uiso d D 1 . . H
  C10 0.3105(2) 0.0950(3) 0.2084(3) 0.0342(10) Uani d . 1 . . C
  O3 0.26438(14) 0.09143(19) 0.1136(2) 0.0455(8) Uani d . 1 . . O
  C11 0.2535(2) 0.3670(3) 0.2016(3) 0.0296(9) Uani d . 1 . . C
  O1 0.20107(13) 0.30448(19) 0.1124(2) 0.0348(7) Uani d . 1 . . O
  H1B 0.231(2) 0.270(3) 0.078(3) 0.052 Uiso d . 1 . . H
  N11 0.35182(18) 0.3513(3) 0.1149(3) 0.0441(9) Uani d . 1 . . N
  C12 0.31824(19) 0.4158(3) 0.1668(3) 0.0283(9) Uani d . 1 . . C
  C13 0.3427(2) 0.5207(3) 0.1888(3) 0.0430(11) Uani d . 1 . . C
  H13A 0.3192 0.5659 0.2270 0.052 Uiso calc R 1 . . H
  C14 0.4019(2) 0.5577(3) 0.1541(3) 0.0489(12) Uani d . 1 . . C
  H14A 0.4185 0.6295 0.1668 0.059 Uiso calc R 1 . . H
  C15 0.4367(2) 0.4921(3) 0.1017(3) 0.0427(11) Uani d . 1 . . C
  H15A 0.4781 0.5163 0.0784 0.051 Uiso calc R 1 . . H
  C16 0.4096(2) 0.3894(4) 0.0839(3) 0.0524(12) Uani d . 1 . . C
  H16A 0.4334 0.3428 0.0474 0.063 Uiso calc R 1 . . H
  C21 0.2011(2) 0.4501(3) 0.2274(3) 0.0303(9) Uani d . 1 . . C
  C22 0.1333(2) 0.4875(3) 0.1453(3) 0.0372(10) Uani d . 1 . . C
  H22A 0.1188 0.4595 0.0733 0.045 Uiso calc R 1 . . H
  C23 0.0867(2) 0.5647(3) 0.1671(4) 0.0441(11) Uani d . 1 . . C
  H23A 0.0407 0.5896 0.1098 0.053 Uiso calc R 1 . . H
  C24 0.1060(2) 0.6061(3) 0.2712(4) 0.0428(11) Uani d . 1 . . C
  H24A 0.0732 0.6586 0.2858 0.051 Uiso calc R 1 . . H
  C25 0.1740(2) 0.5703(3) 0.3546(3) 0.0362(10) Uani d . 1 . . C
  H25A 0.1881 0.5984 0.4265 0.043 Uiso calc R 1 . . H
  C26 0.2205(2) 0.4942(3) 0.3321(3) 0.0352(10) Uani d . 1 . . C
  H26A 0.2672 0.4708 0.3892 0.042 Uiso calc R 1 . . H
  N31 0.37194(17) 0.1592(2) 0.6819(2) 0.0329(8) Uani d . 1 . . N
  C31 0.2970(2) 0.1977(3) 0.6503(3) 0.0286(9) Uani d . 1 . . C
  C33 0.2644(2) 0.2311(3) 0.7252(3) 0.0363(10) Uani d . 1 . . C
  H33A 0.2119 0.2586 0.7010 0.044 Uiso calc R 1 . . H
  C34 0.3086(2) 0.2243(3) 0.8363(3) 0.0455(11) Uani d . 1 . . C
  H34A 0.2867 0.2473 0.8889 0.055 Uiso calc R 1 . . H
  C35 0.3840(2) 0.1842(3) 0.8691(3) 0.0398(11) Uani d . 1 . . C
  H35A 0.4153 0.1771 0.9446 0.048 Uiso calc R 1 . . H
  C36 0.4130(2) 0.1545(3) 0.7901(3) 0.0371(10) Uani d . 1 . . C
  H36A 0.4660 0.1287 0.8133 0.045 Uiso calc R 1 . . H
  C41 0.1615(2) 0.2070(3) 0.4961(3) 0.0317(9) Uani d . 1 . . C
  C42 0.1185(2) 0.2875(3) 0.4307(3) 0.0389(10) Uani d . 1 . . C
  H42A 0.1453 0.3402 0.4050 0.047 Uiso calc R 1 . . H
  C43 0.0359(2) 0.2932(4) 0.4014(3) 0.0503(11) Uani d . 1 . . C
  H43A 0.0073 0.3484 0.3544 0.060 Uiso calc R 1 . . H
  C44 -0.0038(2) 0.2206(4) 0.4395(4) 0.0565(13) Uani d . 1 . . C
  H44A -0.0598 0.2248 0.4199 0.068 Uiso calc R 1 . . H
  C45 0.0393(2) 0.1402(3) 0.5076(4) 0.0550(13) Uani d . 1 . . C
  H45A 0.0125 0.0892 0.5354 0.066 Uiso calc R 1 . . H
  C46 0.1209(2) 0.1338(3) 0.5353(3) 0.0475(11) Uani d . 1 . . C
  H46A 0.1495 0.0784 0.5819 0.057 Uiso calc R 1 . . H
  O4 0.0949(4) -0.0357(5) -0.2518(5) 0.0618(18) Uani d P 0.50 A 2 O
  O5 0.0042(6) 0.0639(4) -0.2129(4) 0.062(3) Uani d P 0.50 . . O
  C51 0.0695(4) 0.0206(6) -0.2068(5) 0.091(2) Uani d . 1 . . C
  H51A 0.0870 -0.0049 -0.2662 0.110 Uiso d PR 0.50 A 1 H
  H51B 0.0644 -0.0419 -0.1639 0.110 Uiso d PR 0.50 A 1 H
  C52 0.1311(3) 0.0926(5) -0.1339(4) 0.0948(19) Uani d . 1 A . C
  H52A 0.1759 0.0505 -0.0866 0.142 Uiso calc R 1 . . H
  H52B 0.1083 0.1337 -0.0886 0.142 Uiso calc R 1 . . H
  H52C 0.1496 0.1409 -0.1785 0.142 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
  C1 0.021(2) 0.030(2) 0.024(2) -0.0010(18) -0.0002(17) 0.0018(19)
  C2 0.024(2) 0.027(2) 0.028(2) -0.0013(18) 0.0022(18) 0.0021(19)
  C3 0.025(2) 0.024(2) 0.033(3) -0.0042(18) 0.0034(19) 0.0023(19)
  C4 0.017(2) 0.033(2) 0.039(3) 0.0006(19) 0.0024(18) 0.001(2)
  C5 0.017(2) 0.030(2) 0.027(2) 0.0037(18) 0.0021(18) 0.0026(19)
  C6 0.027(2) 0.021(2) 0.034(2) -0.0035(17) 0.0088(19) -0.0028(19)
  C7 0.020(2) 0.024(2) 0.029(2) 0.0000(17) 0.0026(18) 0.0019(19)
  C8 0.021(2) 0.027(2) 0.029(2) 0.0034(18) 0.0012(18) 0.0013(19)
  C9 0.034(3) 0.020(2) 0.026(3) 0.0010(19) -0.001(2) -0.0001(18)
  O2 0.0236(15) 0.0449(17) 0.0336(16) 0.0011(13) -0.0016(12) -0.0030(13)
  N1 0.027(2) 0.0277(18) 0.035(2) -0.0001(15) 0.0069(16) -0.0025(17)
  C10 0.028(2) 0.023(2) 0.044(3) -0.0011(19) 0.005(2) -0.006(2)
  O3 0.0341(17) 0.0482(18) 0.0365(19) 0.0016(14) -0.0091(14) -0.0104(15)
  C11 0.026(2) 0.033(2) 0.024(2) -0.0013(19) 0.0019(19) -0.0009(19)
  O1 0.0248(15) 0.0404(16) 0.0298(17) 0.0000(13) -0.0020(12) -0.0039(13)
  N11 0.036(2) 0.055(2) 0.042(2) -0.0059(18) 0.0160(18) -0.0158(18)
  C12 0.024(2) 0.033(2) 0.022(2) 0.0032(19) 0.0008(18) 0.0039(19)
  C13 0.043(3) 0.034(2) 0.060(3) 0.003(2) 0.028(2) 0.002(2)
  C14 0.041(3) 0.041(3) 0.070(3) 0.002(2) 0.026(3) 0.011(2)
  C15 0.027(2) 0.057(3) 0.045(3) 0.001(2) 0.014(2) 0.009(2)
  C16 0.044(3) 0.074(4) 0.049(3) -0.010(3) 0.027(2) -0.020(3)
  C21 0.024(2) 0.031(2) 0.033(3) -0.0003(18) 0.006(2) 0.002(2)
  C22 0.022(2) 0.044(3) 0.037(3) 0.003(2) 0.000(2) -0.006(2)
  C23 0.025(2) 0.047(3) 0.053(3) 0.005(2) 0.005(2) -0.001(2)
  C24 0.032(2) 0.041(3) 0.056(3) 0.004(2) 0.016(2) -0.006(2)
  C25 0.035(3) 0.034(2) 0.039(3) -0.005(2) 0.011(2) -0.004(2)
  C26 0.026(2) 0.037(2) 0.034(3) 0.006(2) 0.0014(19) 0.003(2)
  N31 0.0255(19) 0.0304(19) 0.033(2) 0.0030(15) -0.0011(16) 0.0045(15)
  C31 0.029(2) 0.024(2) 0.032(2) 0.0008(19) 0.0092(19) 0.0031(19)
  C33 0.032(2) 0.045(3) 0.027(3) 0.009(2) 0.005(2) 0.006(2)
  C34 0.055(3) 0.041(3) 0.043(3) 0.010(2) 0.022(2) 0.004(2)
  C35 0.040(3) 0.036(2) 0.036(3) 0.006(2) 0.003(2) 0.007(2)
  C36 0.028(2) 0.031(2) 0.041(3) 0.0018(19) -0.001(2) 0.010(2)
  C41 0.024(2) 0.035(2) 0.034(2) 0.000(2) 0.0075(19) 0.002(2)
  C42 0.027(2) 0.046(3) 0.042(3) 0.007(2) 0.0099(19) 0.005(2)
  C43 0.034(3) 0.066(3) 0.044(3) 0.014(2) 0.006(2) 0.003(3)
  C44 0.023(3) 0.072(3) 0.068(3) 0.004(3) 0.008(2) -0.012(3)
  C45 0.033(3) 0.051(3) 0.082(4) -0.010(2) 0.022(3) -0.010(3)
  C46 0.032(3) 0.051(3) 0.061(3) 0.001(2) 0.017(2) 0.005(2)
  O4 0.067(5) 0.061(4) 0.059(5) 0.016(3) 0.024(4) -0.001(3)
  O5 0.027(4) 0.069(4) 0.076(8) 0.003(4) 0.001(7) -0.018(3)
  C51 0.082(5) 0.142(6) 0.046(4) 0.061(4) 0.018(4) 0.029(4)
  C52 0.068(4) 0.141(5) 0.078(4) 0.024(4) 0.029(3) 0.044(4)
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
  C1 C2 . 1.563(4) ?
  C1 C6 . 1.524(4) ?
  C1 C7 . 1.539(4) ?
  C1 H1A . 1.0000 ?
  C2 C9 . 1.494(4) ?
  C2 C3 . 1.554(4) ?
  C2 H2A . 1.0000 ?
  C3 C10 . 1.501(5) ?
  C3 C4 . 1.579(4) ?
  C3 H3A . 1.0000 ?
  C4 C7 . 1.534(4) ?
  C4 C5 . 1.534(4) ?
  C4 H4A . 1.0000 ?
  C5 C6 . 1.331(4) ?
  C5 C11 . 1.530(4) ?
  C6 H6A . 0.9500 ?
  C7 C8 . 1.323(4) ?
  C8 C41 . 1.500(4) ?
  C8 C31 . 1.505(5) ?
  C9 O2 . 1.238(4) ?
  C9 N1 . 1.371(4) ?
  N1 C10 . 1.385(4) ?
  N1 H1C . 0.92(3) ?
  C10 O3 . 1.222(4) ?
  C11 O1 . 1.445(4) ?
  C11 C12 . 1.523(4) ?
  C11 C21 . 1.525(4) ?
  O1 H1B . 0.93(3) ?
  N11 C16 . 1.332(4) ?
  N11 C12 . 1.334(4) ?
  C12 C13 . 1.392(5) ?
  C13 C14 . 1.379(5) ?
  C13 H13A . 0.9500 ?
  C14 C15 . 1.360(5) ?
  C14 H14A . 0.9500 ?
  C15 C16 . 1.376(5) ?
  C15 H15A . 0.9500 ?
  C16 H16A . 0.9500 ?
  C21 C22 . 1.390(4) ?
  C21 C26 . 1.401(5) ?
  C22 C23 . 1.380(5) ?
  C22 H22A . 0.9500 ?
  C23 C24 . 1.381(5) ?
  C23 H23A . 0.9500 ?
  C24 C25 . 1.393(5) ?
  C24 H24A . 0.9500 ?
  C25 C26 . 1.373(4) ?
  C25 H25A . 0.9500 ?
  C26 H26A . 0.9500 ?
  N31 C36 . 1.343(4) ?
  N31 C31 . 1.353(4) ?
  C31 C33 . 1.373(5) ?
  C33 C34 . 1.388(5) ?
  C33 H33A . 0.9500 ?
  C34 C35 . 1.367(5) ?
  C34 H34A . 0.9500 ?
  C35 C36 . 1.363(5) ?
  C35 H35A . 0.9500 ?
  C36 H36A . 0.9500 ?
  C41 C42 . 1.374(4) ?
  C41 C46 . 1.384(4) ?
  C42 C43 . 1.398(5) ?
  C42 H42A . 0.9500 ?
  C43 C44 . 1.360(5) ?
  C43 H43A . 0.9500 ?
  C44 C45 . 1.389(5) ?
  C44 H44A . 0.9500 ?
  C45 C46 . 1.385(5) ?
  C45 H45A . 0.9500 ?
  C46 H46A . 0.9500 ?
  O4 C51 . 1.119(6) ?
  O5 C51 . 1.272(10) ?
  O5 C51 2_554 1.473(10) ?
  C51 C52 . 1.485(7) ?
  C51 H51A . 0.9900 ?
  C51 H51B . 0.9900 ?
  C52 H52A . 0.9800 ?
  C52 H52B . 0.9800 ?
  C52 H52C . 0.9800 ?