data_2200301
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o461
_journal_page_last  o462
_publ_section_title
;
A bicyclo[3.3.0]octan-2-ylcyclopentanone
;
loop_
_publ_author_name
  'Marcel K. Eberle'
  'Reinhart Keese'
  'Helen Stoeckli-Evans'
_chemical_formula_moiety  'C19 H32 O2 Si'
_chemical_formula_sum  'C19 H32 O2 Si'
_chemical_formula_iupac  'C19 H32 O2 Si'
_chemical_formula_weight  320.54
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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  14.1445(14)
_cell_length_b  6.2718(4)
_cell_length_c  22.340(2)
_cell_angle_alpha  90.00
_cell_angle_beta  103.694(11)
_cell_angle_gamma  90.00
_cell_volume  1925.4(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  223(2)
_exptl_crystal_density_diffrn  1.106
_exptl_crystal_density_meas  none
_diffrn_ambient_temperature  223(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
  Si1  .66534(3)  .63460(7)  .21123(2)  .03578(15) Uani d . 1 . . Si
  C1'  .82283(11)  .2185(3)  .12615(7)  .0361(3) Uani d . 1 . . C
  H1'  .8027  .0675  .1193  .043 Uiso calc R 1 . . H
  C2'  .88120(11)  .2850(2)  .07837(7)  .0357(3) Uani d . 1 . . C
  O2'  .86121(7)  .50559(17)  .06421(5)  .0389(3) Uani d . 1 . . O
  H2'  .9090  .5616  .0550  .058 Uiso calc R 1 . . H
  C3'  .98698(12)  .2578(3)  .11428(8)  .0497(4) Uani d . 1 . . C
  H3'A 1.0067  .1077  .1162  .060 Uiso calc R 1 . . H
  H3'B 1.0313  .3412  .0957  .060 Uiso calc R 1 . . H
  C4'  .98515(11)  .3424(3)  .17772(8)  .0518(4) Uani d . 1 . . C
  H4'A  .9810  .4984  .1776  .062 Uiso calc R 1 . . H
  H4'B 1.0433  .2980  .2085  .062 Uiso calc R 1 . . H
  C5'  .89358(12)  .2420(3)  .19056(7)  .0443(4) Uani d . 1 . . C
  H5'  .9091  .0998  .2096  .053 Uiso calc R 1 . . H
  C6'  .83947(12)  .3758(3)  .22918(7)  .0423(4) Uani d . 1 . . C
  H6'A  .8849  .4668  .2582  .051 Uiso calc R 1 . . H
  H6'B  .8050  .2838  .2525  .051 Uiso calc R 1 . . H
  C7'  .76722(10)  .5115(2)  .18233(6)  .0333(3) Uani d . 1 . . C
  H7'  .8041  .6279  .1683  .040 Uiso calc R 1 . . H
  C8'  .73344(10)  .3562(3)  .12847(6)  .0369(3) Uani d . 1 . . C
  H8'A  .7108  .4345  .0898  .044 Uiso calc R 1 . . H
  H8'B  .6802  .2667  .1353  .044 Uiso calc R 1 . . H
  C1  .90798(14)  .2368(3)  -.02923(8)  .0498(4) Uani d . 1 A . C
  O1  .99521(9)  .2637(2)  -.01939(6)  .0562(4) Uani d . 1 . . O
  C2  .85458(12)  .1553(3)  .01809(7)  .0460(4) Uani d . 1 A . C
  H2  .8750  .0059  .0280  .055 Uiso calc R 1 . . H
  C3  .74763(15)  .1533(5)  -.01618(8)  .0758(7) Uani d D 1 . . C
  H3A  .7129  .2796  -.0056  .091 Uiso calc PR  .564(6) A 1 H
  H3B  .7323  .3041  -.0118  .091 Uiso d PR  .436(6) A 2 H
  C4  .7483(2)  .1520(6)  -.08502(10)  .0968(10) Uani d . 1 A . C
  H4A  .7529  .0060  -.0997  .116 Uiso calc R 1 . . H
  H4B  .6891  .2182  -.1098  .116 Uiso calc R 1 . . H
  C5  .83684(17)  .2794(5)  -.08872(9)  .0795(7) Uani d . 1 . . C
  H5A  .8626  .2325  -.1236  .095 Uiso calc R 1 A . H
  H5B  .8214  .4317  -.0933  .095 Uiso calc R 1 . . H
  C6A  .7037(3)  -.0685(8)  .00554(19)  .0615(13) Uani d PD  .564(6) A 1 C
  H6A  .7440  -.1895  -.0008  .074 Uiso calc PR  .564(6) A 1 H
  H6B  .7046  -.0609  .0495  .074 Uiso calc PR  .564(6) A 1 H
  C7A  .6020(3)  -.0995(7)  -.03112(17)  .0644(14) Uani d PD  .564(6) A 1 C
  H7AA  .5594  .0165  -.0328  .077 Uiso calc PR  .564(6) A 1 H
  C8A  .5665(5)  -.2681(15)  -.0606(6)  .095(2) Uani d PD  .564(6) A 1 C
  H8A  .6061  -.3886  -.0603  .114 Uiso calc PR  .564(6) A 1 H
  H8B  .5010  -.2710  -.0824  .114 Uiso calc PR  .564(6) A 1 H
  C6B  .6572(3)  .0576(8)  -.00667(18)  .0495(15) Uani d PD  .436(6) A 2 C
  H6C  .6003  .1174  -.0356  .059 Uiso calc PR  .436(6) A 2 H
  H6D  .6508  .0825  .0355  .059 Uiso calc PR  .436(6) A 2 H
  C7B  .6669(5)  -.1723(9)  -.0181(3)  .0666(18) Uani d PD  .436(6) A 2 C
  H7B  .7245  -.2394  .0032  .080 Uiso calc PR  .436(6) A 2 H
  C8B  .6038(8)  -.289(2)  -.0545(8)  .121(5) Uani d PD  .436(6) A 2 C
  H8C  .5452  -.2285  -.0767  .145 Uiso calc PR  .436(6) A 2 H
  H8D  .6163  -.4345  -.0589  .145 Uiso calc PR  .436(6) A 2 H
  C10  .59107(13)  .4230(3)  .23706(9)  .0542(5) Uani d . 1 . . C
  H10A  .5399  .4888  .2529  .081 Uiso calc R 1 . . H
  H10B  .6324  .3384  .2692  .081 Uiso calc R 1 . . H
  H10C  .5623  .3317  .2025  .081 Uiso calc R 1 . . H
  C9  .58525(13)  .7890(3)  .14757(8)  .0547(5) Uani d . 1 . . C
  H9A  .6217  .9068  .1360  .082 Uiso calc R 1 . . H
  H9B  .5299  .8439  .1613  .082 Uiso calc R 1 . . H
  H9C  .5626  .6965  .1123  .082 Uiso calc R 1 . . H
  C11  .71678(14)  .8137(3)  .27794(9)  .0563(5) Uani d . 1 . . C
  H11A  .7574  .7311  .3109  .084 Uiso calc R 1 . . H
  H11B  .6641  .8783  .2925  .084 Uiso calc R 1 . . H
  H11C  .7555  .9244  .2650  .084 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
  Si1  .0399(2)  .0337(3)  .0387(2)  -.00322(18)  .01918(17)  -.00023(18)
  C1'  .0428(8)  .0294(8)  .0382(8)  -.0011(6)  .0139(6)  -.0002(6)
  C2'  .0370(7)  .0312(8)  .0418(8)  .0036(6)  .0149(6)  .0003(6)
  O2'  .0386(6)  .0325(6)  .0503(6)  .0047(4)  .0201(5)  .0042(5)
  C3'  .0397(9)  .0509(12)  .0605(10)  .0130(7)  .0158(8)  .0001(8)
  C4'  .0353(8)  .0621(12)  .0538(10)  .0120(8)  .0021(7)  -.0015(9)
  C5'  .0502(9)  .0395(10)  .0411(9)  .0112(7)  .0064(7)  .0069(7)
  C6'  .0480(9)  .0450(10)  .0329(7)  .0004(7)  .0072(6)  .0001(7)
  C7'  .0347(7)  .0321(9)  .0353(7)  -.0039(6)  .0130(6)  .0006(6)
  C8'  .0336(7)  .0448(9)  .0339(7)  -.0031(6)  .0110(6)  -.0030(7)
  C1  .0659(12)  .0386(10)  .0554(10)  .0020(8)  .0355(9)  -.0072(8)
  O1  .0622(8)  .0432(8)  .0764(9)  .0032(6)  .0425(7)  .0000(6)
  C2  .0575(10)  .0404(10)  .0482(9)  -.0036(7)  .0286(8)  -.0070(7)
  C3  .0646(12)  .124(2)  .0445(10)  -.0364(13)  .0251(9)  -.0349(12)
  C4  .0954(18)  .154(3)  .0467(12)  -.0386(18)  .0274(12)  -.0288(14)
  C5  .0872(16)  .110(2)  .0481(11)  -.0068(14)  .0300(11)  -.0007(12)
  C6A  .046(2)  .068(3)  .060(2)  -.013(2)  -.0082(17)  .008(2)
  C7A  .041(2)  .078(3)  .065(2)  -.001(2)  -.0053(17)  -.006(2)
  C8A  .055(4)  .073(4)  .127(5)  -.004(3)  -.036(4)  -.019(3)
  C6B  .040(2)  .068(3)  .037(2)  .003(2)  .0019(17)  -.004(2)
  C7B  .060(4)  .057(4)  .072(3)  -.001(3)  -.005(3)  .007(3)
  C8B  .085(8)  .092(6)  .143(7)  .016(7)  -.061(8)  -.025(5)
  C10  .0565(10)  .0560(12)  .0594(11)  -.0118(9)  .0327(8)  .0016(9)
  C9  .0558(10)  .0582(12)  .0549(10)  .0148(9)  .0230(8)  .0090(9)
  C11  .0653(12)  .0505(12)  .0579(11)  -.0055(9)  .0242(9)  -.0147(9)
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
  Si1 C9 . 1.8655(18) ?
  Si1 C10 . 1.8671(17) ?
  Si1 C11 . 1.8704(18) ?
  Si1 C7' . 1.8788(15) ?
  C1' C8' . 1.542(2) ?
  C1' C5' . 1.553(2) ?
  C1' C2' . 1.553(2) ?
  C2' O2' . 1.4321(19) ?
  C2' C3' . 1.531(2) ?
  C2' C2 . 1.542(2) ?
  C3' C4' . 1.519(3) ?
  C4' C5' . 1.527(2) ?
  C5' C6' . 1.532(2) ?
  C6' C7' . 1.535(2) ?
  C7' C8' . 1.534(2) ?
  C1 O1 . 1.213(2) ?
  C1 C5 . 1.489(3) ?
  C1 C2 . 1.526(2) ?
  C2 C3 . 1.525(3) ?
  C3 C6B . 1.473(4) ?
  C3 C4 . 1.540(3) ?
  C3 C6A . 1.643(5) ?
  C4 C5 . 1.504(3) ?
  C6A C7A . 1.490(5) ?
  C7A C8A . 1.283(10) ?
  C6B C7B . 1.477(8) ?
  C7B C8B . 1.283(12) ?