#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007127.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_2007127
_journal_name_full  'Acta Crystallographica'
_journal_year  1998
_journal_volume  C54
_journal_page_first  392
_journal_page_last  398
_publ_section_title
;
Synthesis and Absolute Structure Determination of Camphanoate Derivatives
 of Five Bicyclo[3.1.0]hexane Compounds
;
loop_
_publ_author_name
  'Krief, Alain'
  'Ollevier, Thierry'
  'Swinnen, Dominique'
  'Norberg, Bernadette'
  'Baudoux, Guy'
  'Evrard, Guy'
_chemical_formula_moiety  'C21 H30 O6'
_chemical_formula_weight  756.90
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P 2y1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  14.7140(10)
_cell_length_b  11.0010(10)
_cell_length_c  14.736(2)
_cell_angle_alpha  90.00
_cell_angle_beta  118.527(8)
_cell_angle_gamma  90.00
_cell_volume  2095.7(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  292(2)
_exptl_crystal_density_diffrn  1.199
_diffrn_ambient_temperature  292(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 1.09245(15)  .0216(3)  -.02667(16)  .0630(5) Uani d . 1 . . O
  O2  .9322(2)  -.0443(4)  -.1136(3)  .1330(15) Uani d . 1 . . O
  O3 1.30538(14)  .1263(3)  .01883(18)  .0637(6) Uani d . 1 . . O
  O4 1.4634(2)  .1532(6)  .0500(4)  .212(3) Uani d . 1 . . O
  O5 1.50536(14)  .2780(3)  .22548(15)  .0603(5) Uani d . 1 . . O
  O6 1.59565(19)  .4180(3)  .3435(2)  .0993(9) Uani d . 1 . . O
  C1 1.1098(2)  .0048(4)  -.1837(2)  .0621(8) Uani d . 1 . . C
  H1 1.0673  -.0349  -.2503  .075 Uiso calc R 1 . . H
  C2 1.1240(2)  -.0559(4)  -.0867(2)  .0608(7) Uani d . 1 . . C
  H2 1.0850  -.1322  -.1037  .073 Uiso calc R 1 . . H
  C3 1.2393(3)  -.0819(3)  -.0231(3)  .0638(8) Uani d . 1 . . C
  C4 1.2893(2)  .0237(3)  -.0509(3)  .0591(7) Uani d . 1 . . C
  H4 1.3553  -.0020  -.0458  .071 Uiso calc R 1 . . H
  C5 1.2142(2)  .0577(3)  -.1605(3)  .0624(8) Uani d . 1 . . C
  H5 1.2366  .0513  -.2132  .075 Uiso calc R 1 . . H
  C6 1.1249(2)  .1405(4)  -.1803(3)  .0626(7) Uani d . 1 . . C
  H6 1.1292  .1818  -.1195  .075 Uiso calc R 1 . . H
  C7 1.2791(3)  -.0988(4)  .0926(3)  .0844(11) Uani d . 1 . . C
  H7A 1.3521  -.1146  .1259  .127 Uiso calc R 1 . . H
  H7B 1.2441  -.1661  .1037  .127 Uiso calc R 1 . . H
  H7C 1.2662  -.0262  .1208  .127 Uiso calc R 1 . . H
  C8 1.2616(4)  -.1980(4)  -.0684(4)  .0965(13) Uani d . 1 . . C
  H8A 1.3339  -.2173  -.0302  .145 Uiso calc R 1 . . H
  H8B 1.2430  -.1843  -.1395  .145 Uiso calc R 1 . . H
  H8C 1.2217  -.2644  -.0636  .145 Uiso calc R 1 . . H
  C9  .9930(2)  .0230(4)  -.0520(2)  .0660(8) Uani d . 1 . . C
  C10  .9681(3)  .1213(5)  .0013(3)  .0872(12) Uani d . 1 . . C
  H10A 1.0305  .1633  .0475  .131 Uiso calc R 1 . . H
  H10B  .9371  .0870  .0398  .131 Uiso calc R 1 . . H
  H10C  .9208  .1775  -.0489  .131 Uiso calc R 1 . . H
  C11 1.3953(2)  .1765(4)  .0683(2)  .0652(8) Uani d . 1 . . C
  C12 1.39975(18)  .2735(3)  .14098(19)  .0455(6) Uani d . 1 . . C
  C13 1.3310(2)  .2607(4)  .1916(2)  .0582(7) Uani d . 1 . . C
  H13A 1.3554  .1966  .2430  .070 Uiso calc R 1 . . H
  H13B 1.2598  .2446  .1408  .070 Uiso calc R 1 . . H
  C14 1.3424(2)  .3853(4)  .2410(2)  .0652(8) Uani d . 1 . . C
  H14A 1.3723  .3785  .3154  .078 Uiso calc R 1 . . H
  H14B 1.2760  .4259  .2139  .078 Uiso calc R 1 . . H
  C15 1.4159(2)  .4548(3)  .2112(2)  .0605(7) Uani d . 1 . . C
  C16 1.5170(2)  .3882(4)  .2696(2)  .0660(8) Uani d . 1 . . C
  C17 1.4219(4)  .5906(4)  .2283(4)  .1057(15) Uani d . 1 . . C
  H17A 1.3544  .6256  .1885  .159 Uiso calc R 1 . . H
  H17B 1.4686  .6253  .2070  .159 Uiso calc R 1 . . H
  H17C 1.4465  .6072  .3003  .159 Uiso calc R 1 . . H
  C18 1.3821(2)  .4058(3)  .1011(2)  .0543(7) Uani d . 1 . . C
  C19 1.2710(3)  .4320(4)  .0212(3)  .0812(10) Uani d . 1 . . C
  H19A 1.2255  .4074  .0476  .122 Uiso calc R 1 . . H
  H19B 1.2543  .3878  -.0410  .122 Uiso calc R 1 . . H
  H19C 1.2629  .5176  .0065  .122 Uiso calc R 1 . . H
  C20 1.4554(3)  .4448(5)  .0599(3)  .0969(13) Uani d . 1 . . C
  H20A 1.5255  .4280  .1108  .145 Uiso calc R 1 . . H
  H20B 1.4476  .5304  .0452  .145 Uiso calc R 1 . . H
  H20C 1.4391  .4006  -.0022  .145 Uiso calc R 1 . . H
  C21 1.0762(3)  .2119(4)  -.2788(3)  .0886(11) Uani d . 1 . . C
  H21A 1.0931  .2964  -.2638  .133 Uiso calc R 1 . . H
  H21B 1.0025  .2019  -.3119  .133 Uiso calc R 1 . . H
  H21C 1.1019  .1833  -.3239  .133 Uiso calc R 1 . . H
  O31 1.42353(15)  .4187(3)  .61981(17)  .0609(5) Uani d . 1 . . O
  O32 1.5303(3)  .5542(4)  .6093(3)  .1236(14) Uani d . 1 . . O
  O33 1.19027(13)  .3301(3)  .54739(14)  .0489(4) Uani d . 1 . . O
  O34 1.01962(16)  .3572(3)  .4484(2)  .0841(8) Uani d . 1 . . O
  O35  .99611(13)  .1423  .35455(15)  .0573(5) Uani d . 1 . . O
  O36  .93512(16)  .0155(3)  .21868(17)  .0763(6) Uani d . 1 . . O
  C31 1.3082(2)  .5953(3)  .5638(3)  .0618(8) Uani d . 1 . . C
  H31 1.3228  .6826  .5678  .074 Uiso calc R 1 . . H
  C32 1.3774(2)  .5152(3)  .6524(2)  .0588(7) Uani d . 1 . . C
  H32 1.4317  .5639  .7071  .071 Uiso calc R 1 . . H
  C33 1.3071(2)  .4577(4)  .6918(2)  .0579(7) Uani d . 1 . . C
  C34 1.2000(2)  .4486(3)  .5955(2)  .0514(6) Uani d . 1 . . C
  H34 1.1457  .4586  .6153  .062 Uiso calc R 1 . . H
  C35 1.1959(2)  .5526(3)  .5263(2)  .0569(7) Uani d . 1 . . C
  H35 1.1415  .6140  .5069  .068 Uiso calc R 1 . . H
  C36 1.2467(2)  .5371(4)  .4596(2)  .0621(7) Uani d . 1 . . C
  H36 1.2668  .4536  .4539  .074 Uiso calc R 1 . . H
  C37 1.3483(3)  .3381(4)  .7499(3)  .0727(9) Uani d . 1 . . C
  H37A 1.3010  .3076  .7721  .109 Uiso calc R 1 . . H
  H37B 1.4146  .3517  .8090  .109 Uiso calc R 1 . . H
  H37C 1.3551  .2798  .7050  .109 Uiso calc R 1 . . H
  C38 1.2955(3)  .5534(4)  .7623(3)  .0816(11) Uani d . 1 . . C
  H38A 1.2697  .6279  .7246  .122 Uiso calc R 1 . . H
  H38B 1.3616  .5679  .8214  .122 Uiso calc R 1 . . H
  H38C 1.2480  .5240  .7846  .122 Uiso calc R 1 . . H
  C39 1.5003(2)  .4501(4)  .6013(2)  .0676(8) Uani d . 1 . . C
  C40 1.5413(3)  .3470(4)  .5670(3)  .0789(10) Uani d . 1 . . C
  H40A 1.5057  .2738  .5666  .118 Uiso calc R 1 . . H
  H40B 1.6139  .3378  .6135  .118 Uiso calc R 1 . . H
  H40C 1.5310  .3628  .4986  .118 Uiso calc R 1 . . H
  C41 1.09587(19)  .2960(3)  .4761(2)  .0475(6) Uani d . 1 . . C
  C42 1.09976(18)  .1718(3)  .43566(19)  .0435(5) Uani d . 1 . . C
  C43 1.1329(3)  .0635(3)  .5106(2)  .0575(7) Uani d . 1 . . C
  H43A 1.1975  .0799  .5726  .069 Uiso calc R 1 . . H
  H43B 1.0801  .0432  .5298  .069 Uiso calc R 1 . . H
  C44 1.1455(3)  -.0378(3)  .4458(2)  .0589(7) Uani d . 1 . . C
  H44A 1.0975  -.1038  .4343  .071 Uiso calc R 1 . . H
  H44B 1.2154  -.0696  .4794  .071 Uiso calc R 1 . . H
  C45 1.1207(2)  .0262(3)  .34261(19)  .0468(6) Uani d . 1 . . C
  C46 1.0082(2)  .0549(3)  .2947(2)  .0549(7) Uani d . 1 . . C
  C47 1.1524(3)  -.0415(4)  .2731(2)  .0643(8) Uani d . 1 . . C
  H47A 1.2255  -.0565  .3095  .096 Uiso calc R 1 . . H
  H47B 1.1357  .0063  .2127  .096 Uiso calc R 1 . . H
  H47C 1.1161  -.1176  .2530  .096 Uiso calc R 1 . . H
  C48 1.16524(17)  .1562(3)  .37938(18)  .0405(5) Uani d . 1 . . C
  C49 1.1349(2)  .2459(3)  .2915(2)  .0563(7) Uani d . 1 . . C
  H49A 1.0612  .2440  .2481  .084 Uiso calc R 1 . . H
  H49B 1.1685  .2244  .2517  .084 Uiso calc R 1 . . H
  H49C 1.1557  .3263  .3192  .084 Uiso calc R 1 . . H
  C50 1.28220(19)  .1588(3)  .4487(2)  .0573(7) Uani d . 1 . . C
  H50A 1.3011  .1019  .5042  .086 Uiso calc R 1 . . H
  H50B 1.3032  .2391  .4765  .086 Uiso calc R 1 . . H
  H50C 1.3159  .1371  .4090  .086 Uiso calc R 1 . . H
  C51 1.2114(3)  .6128(4)  .3644(3)  .0860(11) Uani d . 1 . . C
  H51A 1.2511  .5924  .3305  .129 Uiso calc R 1 . . H
  H51B 1.2209  .6973  .3830  .129 Uiso calc R 1 . . H
  H51C 1.1395  .5974  .3186  .129 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  .0582(11)  .0641(12)  .0774(13)  -.0142(10)  .0409(10)  -.0203(11)
  O2  .0609(16)  .185(4)  .147(3)  -.034(2)  .0453(17)  -.094(3)
  O3  .0510(11)  .0592(12)  .0902(14)  -.0098(9)  .0411(11)  -.0291(11)
  O4  .0658(18)  .299(6)  .278(5)  -.049(3)  .087(3)  -.226(5)
  O5  .0425(10)  .0623(12)  .0562(11)  .0093(9)  .0075(8)  -.0064(10)
  O6  .0657(15)  .116(2)  .0813(16)  -.0102(14)  .0065(12)  -.0355(17)
  C1  .0634(18)  .0592(18)  .0657(18)  -.0076(14)  .0323(15)  -.0192(15)
  C2  .0649(17)  .0522(16)  .0745(18)  -.0145(14)  .0406(15)  -.0174(15)
  C3  .0714(19)  .0457(16)  .084(2)  .0008(14)  .0452(17)  -.0041(15)
  C4  .0578(16)  .0485(15)  .083(2)  -.0030(13)  .0438(16)  -.0156(15)
  C5  .0736(19)  .0579(17)  .0743(19)  -.0064(15)  .0503(16)  -.0142(15)
  C6  .0730(19)  .0552(17)  .0708(18)  .0014(15)  .0434(16)  -.0059(15)
  C7  .085(2)  .077(2)  .087(2)  .0012(19)  .038(2)  .015(2)
  C8  .114(3)  .0475(19)  .145(4)  .0066(19)  .075(3)  -.014(2)
  C9  .0539(16)  .087(2)  .0565(15)  -.0084(17)  .0259(13)  -.0099(17)
  C10  .071(2)  .117(3)  .076(2)  .012(2)  .0362(19)  -.021(2)
  C11  .0386(14)  .083(2)  .0707(18)  .0099(14)  .0231(13)  -.0187(17)
  C12  .0360(12)  .0507(14)  .0458(13)  .0041(11)  .0162(10)  -.0009(12)
  C13  .0641(17)  .0641(18)  .0597(16)  -.0007(14)  .0404(14)  .0058(14)
  C14  .0658(18)  .075(2)  .0646(17)  -.0018(16)  .0389(15)  -.0105(16)
  C15  .0578(16)  .0491(16)  .0736(18)  .0007(13)  .0304(14)  -.0013(15)
  C16  .0537(16)  .074(2)  .0609(17)  -.0085(15)  .0199(14)  -.0122(16)
  C17  .103(3)  .056(2)  .154(4)  -.011(2)  .057(3)  -.025(3)
  C18  .0493(14)  .0617(18)  .0574(15)  .0016(13)  .0299(12)  .0118(14)
  C19  .0636(19)  .086(3)  .074(2)  .0177(18)  .0173(16)  .032(2)
  C20  .089(3)  .130(4)  .085(2)  -.022(3)  .052(2)  .025(3)
  C21  .101(3)  .085(3)  .087(2)  .016(2)  .050(2)  .012(2)
  O31  .0526(10)  .0615(12)  .0807(13)  -.0114(9)  .0415(10)  -.0099(11)
  O32  .131(3)  .105(2)  .199(4)  -.066(2)  .130(3)  -.063(2)
  O33  .0467(9)  .0423(10)  .0614(11)  -.0055(7)  .0288(8)  -.0085(8)
  O34  .0503(12)  .0804(16)  .1050(17)  .0149(11)  .0235(12)  -.0324(14)
  O35  .0383(9)  .0698(12)  .0651(11)  -.0091(9)  .0257(8)  -.0215(10)
  O36  .0542(12)  .0920(16)  .0712(13)  -.0170(11)  .0206(11)  -.0313(13)
  C31  .0732(19)  .0449(15)  .0798(19)  -.0181(14)  .0467(17)  -.0168(15)
  C32  .0601(16)  .0544(16)  .0694(17)  -.0180(14)  .0370(14)  -.0187(15)
  C33  .0579(16)  .0620(17)  .0621(16)  -.0146(14)  .0354(14)  -.0156(15)
  C34  .0539(14)  .0451(14)  .0678(16)  -.0063(12)  .0391(13)  -.0129(13)
  C35  .0636(17)  .0419(15)  .0746(18)  .0012(13)  .0406(15)  -.0045(13)
  C36  .077(2)  .0470(16)  .0751(19)  -.0017(15)  .0468(17)  -.0006(15)
  C37  .0664(19)  .084(2)  .0681(19)  -.0100(18)  .0321(16)  .0076(18)
  C38  .082(2)  .098(3)  .082(2)  -.028(2)  .054(2)  -.031(2)
  C39  .0566(17)  .085(2)  .0705(19)  -.0191(17)  .0378(15)  -.0169(18)
  C40  .0608(18)  .098(3)  .090(2)  .0011(19)  .0458(18)  -.008(2)
  C41  .0433(13)  .0535(15)  .0526(13)  -.0028(12)  .0285(11)  -.0049(12)
  C42  .0356(11)  .0506(14)  .0478(13)  -.0053(10)  .0229(10)  -.0023(11)
  C43  .0738(19)  .0514(16)  .0553(15)  -.0123(14)  .0373(14)  -.0006(13)
  C44  .0767(19)  .0431(15)  .0569(15)  -.0078(14)  .0320(15)  -.0011(13)
  C45  .0500(13)  .0430(14)  .0501(13)  -.0009(11)  .0261(11)  -.0020(12)
  C46  .0515(15)  .0599(17)  .0538(14)  -.0081(13)  .0254(13)  -.0064(14)
  C47  .0716(19)  .0580(18)  .0690(18)  .0070(15)  .0381(16)  -.0105(15)
  C48  .0385(11)  .0398(13)  .0478(12)  -.0021(10)  .0243(10)  -.0004(11)
  C49  .0681(18)  .0511(16)  .0570(15)  -.0023(13)  .0359(14)  .0057(13)
  C50  .0397(13)  .0604(17)  .0755(18)  -.0025(12)  .0306(13)  -.0119(15)
  C51  .110(3)  .065(2)  .094(3)  .012(2)  .058(2)  .018(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
  O1 C9 . 1.327(3) ?
  O1 C2 . 1.455(3) ?
  O2 C9 . 1.181(4) ?
  O3 C11 . 1.291(3) ?
  O3 C4 . 1.467(3) ?
  O4 C11 . 1.183(4) ?
  O5 C16 . 1.348(4) ?
  O5 C12 . 1.456(3) ?
  O6 C16 . 1.195(4) ?
  C1 C2 . 1.499(5) ?
  C1 C6 . 1.506(5) ?
  C1 C5 . 1.521(4) ?
  C1 H1 .  .9800 ?
  C2 C3 . 1.523(4) ?
  C2 H2 .  .9800 ?
  C3 C7 . 1.526(5) ?
  C3 C4 . 1.531(4) ?
  C3 C8 . 1.547(5) ?
  C4 C5 . 1.506(5) ?
  C4 H4 .  .9800 ?
  C5 C6 . 1.508(4) ?
  C5 H5 .  .9800 ?
  C6 C21 . 1.498(5) ?
  C6 H6 .  .9800 ?
  C7 H7A .  .9600 ?
  C7 H7B .  .9600 ?
  C7 H7C .  .9600 ?
  C8 H8A .  .9600 ?
  C8 H8B .  .9600 ?
  C8 H8C .  .9600 ?
  C9 C10 . 1.482(5) ?
  C10 H10A .  .9600 ?
  C10 H10B .  .9600 ?
  C10 H10C .  .9600 ?
  C11 C12 . 1.492(4) ?
  C12 C13 . 1.523(4) ?
  C12 C18 . 1.544(4) ?
  C13 C14 . 1.524(5) ?
  C13 H13A .  .9700 ?
  C13 H13B .  .9700 ?
  C14 C15 . 1.548(4) ?
  C14 H14A .  .9700 ?
  C14 H14B .  .9700 ?
  C15 C16 . 1.507(4) ?
  C15 C17 . 1.511(5) ?
  C15 C18 . 1.549(4) ?
  C17 H17A .  .9600 ?
  C17 H17B .  .9600 ?
  C17 H17C .  .9600 ?
  C18 C19 . 1.518(4) ?
  C18 C20 . 1.531(4) ?
  C19 H19A .  .9600 ?
  C19 H19B .  .9600 ?
  C19 H19C .  .9600 ?
  C20 H20A .  .9600 ?
  C20 H20B .  .9600 ?
  C20 H20C .  .9600 ?
  C21 H21A .  .9600 ?
  C21 H21B .  .9600 ?
  C21 H21C .  .9600 ?
  O31 C39 . 1.328(3) ?
  O31 C32 . 1.459(4) ?
  O32 C39 . 1.213(4) ?
  O33 C41 . 1.334(3) ?
  O33 C34 . 1.457(3) ?
  O34 C41 . 1.201(3) ?
  O35 C46 . 1.373(3) ?
  O35 C42 . 1.456(3) ?
  O36 C46 . 1.203(3) ?
  C31 C32 . 1.498(5) ?
  C31 C36 . 1.504(5) ?
  C31 C35 . 1.543(4) ?
  C31 H31 .  .9800 ?
  C32 C33 . 1.542(4) ?
  C32 H32 .  .9800 ?
  C33 C37 . 1.528(5) ?
  C33 C34 . 1.540(4) ?
  C33 C38 . 1.546(4) ?
  C34 C35 . 1.515(4) ?
  C34 H34 .  .9800 ?
  C35 C36 . 1.501(4) ?
  C35 H35 .  .9800 ?
  C36 C51 . 1.495(5) ?
  C36 H36 .  .9800 ?
  C37 H37A .  .9600 ?
  C37 H37B .  .9600 ?
  C37 H37C .  .9600 ?
  C38 H38A .  .9600 ?
  C38 H38B .  .9600 ?
  C38 H38C .  .9600 ?
  C39 C40 . 1.482(5) ?
  C40 H40A .  .9600 ?
  C40 H40B .  .9600 ?
  C40 H40C .  .9600 ?
  C41 C42 . 1.502(4) ?
  C42 C43 . 1.537(4) ?
  C42 C48 . 1.552(3) ?
  C43 C44 . 1.535(4) ?
  C43 H43A .  .9700 ?
  C43 H43B .  .9700 ?
  C44 C45 . 1.553(4) ?
  C44 H44A .  .9700 ?
  C44 H44B .  .9700 ?
  C45 C46 . 1.491(4) ?
  C45 C47 . 1.509(4) ?
  C45 C48 . 1.558(4) ?
  C47 H47A .  .9600 ?
  C47 H47B .  .9600 ?
  C47 H47C .  .9600 ?
  C48 C49 . 1.516(4) ?
  C48 C50 . 1.525(3) ?
  C49 H49A .  .9600 ?
  C49 H49B .  .9600 ?
  C49 H49C .  .9600 ?
  C50 H50A .  .9600 ?
  C50 H50B .  .9600 ?
  C50 H50C .  .9600 ?
  C51 H51A .  .9600 ?
  C51 H51B .  .9600 ?
  C51 H51C .  .9600 ?