#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012880.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_2012880
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o518
_journal_page_last  o520
_publ_section_title
;
(1S,3R,8S,9S,10R)-2,2-Dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3^]-
9,10-epoxydodecane and
(1S,3R,8S,10R)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3^]dodec-
9-one
;
loop_
_publ_author_name
  'Sbai, F.'
  'Dakir, M.'
  'Auhmani, A.'
  'El Jamili, H.'
  'Akssira, M.'
  'Benharref, A.'
  'Kenz, A.'
  'Pierrot, M.'
_chemical_name_common  'dodec-9-one'
_chemical_formula_moiety  'C16 H24 Cl2 O'
_chemical_formula_sum  'C16 H24 Cl2 O'
_chemical_formula_weight  303.24
_chemical_melting_point  363
_symmetry_cell_setting  'Monoclinic'
_symmetry_space_group_name_H-M  'P 21'
_symmetry_space_group_name_Hall  'P_2yb'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  8.9545(4)
_cell_length_b  10.6231(6)
_cell_length_c  9.0858(6)
_cell_angle_alpha  90
_cell_angle_beta  109.497(4)
_cell_angle_gamma  90
_cell_volume  814.78(8)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.232
_diffrn_ambient_temperature  293(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
  Cl1 0.87348(17) 0.45555(10) 0.11114(18) 0.0659(5) Uani d . 1 . . Cl
  Cl2 0.98526(18) 0.26217(14) -0.04459(15) 0.0694(5) Uani d . 1 . . Cl
  O12 0.9920(6) 0.3241(5) 0.5582(5) 0.0799(13) Uani d . 1 . . O
  C1 0.8097(4) 0.2435(4) 0.3241(4) 0.0382(8) Uani d . 1 . . C
  H1 0.7781 0.3303 0.3118 0.046 Uiso d R 1 . . H
  C2 0.9650(5) 0.2411(5) 0.4619(4) 0.0475(10) Uani d . 1 . . C
  C3 1.0803(5) 0.1338(5) 0.4744(5) 0.0535(12) Uani d . 1 . . C
  H3 1.0390 0.0629 0.5139 0.064 Uiso d R 1 . . H
  C4 1.0916(5) 0.0988(5) 0.3167(6) 0.0563(12) Uani d . 1 . . C
  H4A 1.1414 0.1669 0.2813 0.068 Uiso d R 1 . . H
  H4B 1.1539 0.0239 0.3261 0.068 Uiso d R 1 . . H
  C5 0.9296(5) 0.0769(4) 0.1953(5) 0.0457(9) Uani d . 1 . . C
  H5A 0.9433 0.0549 0.0982 0.055 Uiso d R 1 . . H
  H5B 0.8773 0.0093 0.2287 0.055 Uiso d R 1 . . H
  C6 0.8326(5) 0.1967(4) 0.1744(4) 0.0363(8) Uani d . 1 . . C
  C7 0.7003(5) 0.2271(5) 0.0194(5) 0.0501(10) Uani d . 1 . . C
  C8 0.5582(6) 0.2983(6) 0.0303(7) 0.0694(15) Uani d . 1 . . C
  H8A 0.5943 0.3689 0.0990 0.083 Uiso d R 1 . . H
  H8B 0.4952 0.3278 -0.0714 0.083 Uiso d R 1 . . H
  C9 0.4525(6) 0.2185(8) 0.0933(7) 0.0780(18) Uani d . 1 . . C
  H9A 0.3921 0.2718 0.1376 0.094 Uiso d R 1 . . H
  H9B 0.3818 0.1697 0.0100 0.094 Uiso d R 1 . . H
  C10 0.5414(7) 0.1263(7) 0.2240(7) 0.0727(16) Uani d . 1 . . C
  H10A 0.4687 0.0832 0.2639 0.087 Uiso d R 1 . . H
  H10B 0.5954 0.0661 0.1809 0.087 Uiso d R 1 . . H
  C11 0.6695(5) 0.1791(5) 0.3672(5) 0.0504(11) Uani d . 1 . . C
  C13 1.2398(7) 0.1615(8) 0.5996(8) 0.086(2) Uani d . 1 . . C
  H13A 1.3118 0.0930 0.6067 0.104 Uiso d R 1 . . H
  H13B 1.2255 0.1734 0.6989 0.104 Uiso d R 1 . . H
  H13C 1.2822 0.2370 0.5710 0.104 Uiso d R 1 . . H
  C14 0.8573(5) 0.2942(4) 0.0623(5) 0.0457(9) Uani d . 1 . . C
  C15 0.6588(9) 0.1317(7) -0.1114(6) 0.0787(19) Uani d . 1 . . C
  H15A 0.5746 0.1645 -0.1990 0.094 Uiso d R 1 . . H
  H15B 0.6245 0.0555 -0.0759 0.094 Uiso d R 1 . . H
  H15C 0.7494 0.1145 -0.1422 0.094 Uiso d R 1 . . H
  C16 0.6035(10) 0.2806(8) 0.4507(10) 0.089(2) Uani d . 1 . . C
  H16A 0.5184 0.2452 0.4793 0.106 Uiso d R 1 . . H
  H16B 0.5643 0.3493 0.3797 0.106 Uiso d R 1 . . H
  H16C 0.6846 0.3105 0.5427 0.106 Uiso d R 1 . . H
  C17 0.7252(8) 0.0713(7) 0.4854(7) 0.0730(16) Uani d . 1 . . C
  H17A 0.6351 0.0368 0.5061 0.088 Uiso d R 1 . . H
  H17B 0.7999 0.1024 0.5808 0.088 Uiso d R 1 . . H
  H17C 0.7742 0.0069 0.4431 0.088 Uiso d 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
  Cl1 0.0838(8) 0.0341(6) 0.0952(9) -0.0009(5) 0.0501(7) 0.0086(5)
  Cl2 0.0908(10) 0.0646(8) 0.0767(8) 0.0040(7) 0.0596(7) 0.0087(6)
  O12 0.086(3) 0.076(3) 0.066(2) -0.017(2) 0.0087(19) -0.031(2)
  C1 0.0406(18) 0.036(2) 0.0424(17) -0.0047(15) 0.0200(14) -0.0046(15)
  C2 0.052(2) 0.048(3) 0.0418(19) -0.0123(18) 0.0139(17) -0.0050(17)
  C3 0.048(2) 0.056(3) 0.050(2) -0.007(2) 0.0081(18) 0.0100(19)
  C4 0.046(2) 0.053(3) 0.071(3) 0.012(2) 0.022(2) 0.012(2)
  C5 0.060(2) 0.033(2) 0.050(2) 0.0051(18) 0.0266(18) 0.0033(16)
  C6 0.0407(18) 0.0330(19) 0.0387(16) 0.0003(14) 0.0178(13) 0.0010(14)
  C7 0.052(2) 0.053(3) 0.0411(18) 0.000(2) 0.0099(16) 0.0080(17)
  C8 0.047(2) 0.075(4) 0.078(3) 0.008(2) 0.010(2) 0.015(3)
  C9 0.037(2) 0.105(5) 0.085(3) -0.006(3) 0.012(2) 0.005(3)
  C10 0.055(3) 0.084(4) 0.085(3) -0.026(3) 0.030(3) -0.003(3)
  C11 0.049(2) 0.056(3) 0.057(2) -0.009(2) 0.0311(18) -0.003(2)
  C13 0.054(3) 0.105(5) 0.079(3) -0.014(3) -0.006(3) 0.017(4)
  C14 0.055(2) 0.038(2) 0.050(2) 0.0027(17) 0.0258(17) 0.0069(17)
  C15 0.097(4) 0.090(5) 0.041(2) -0.024(4) 0.012(2) -0.009(3)
  C16 0.095(4) 0.091(5) 0.115(5) -0.008(4) 0.081(4) -0.018(4)
  C17 0.077(3) 0.080(4) 0.074(3) -0.013(3) 0.040(3) 0.015(3)
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
  Cl1 C14 . 1.764(5) n
  Cl2 C14 . 1.765(5) n
  O12 C2 . 1.208(6) y
  C1 C2 . 1.530(5) y
  C1 C6 . 1.525(5) y
  C1 C11 . 1.590(5) y
  C1 H1 . 0.9601 n
  C2 C3 . 1.517(7) y
  C3 C4 . 1.516(7) n
  C3 C13 . 1.528(6) n
  C3 H3 . 0.9600 n
  C4 C5 . 1.519(6) n
  C4 H4A . 0.9600 n
  C4 H4B . 0.9600 n
  C5 C6 . 1.516(5) n
  C5 H5A . 0.9600 n
  C5 H5B . 0.9600 n
  C6 C14 . 1.520(5) y
  C6 C7 . 1.543(5) y
  C7 C14 . 1.507(6) y
  C7 C15 . 1.511(8) n
  C7 C8 . 1.512(8) n
  C8 C9 . 1.518(9) n
  C8 H8A . 0.9600 n
  C8 H8B . 0.9601 n
  C9 C10 . 1.540(9) n
  C9 H9A . 0.9599 n
  C9 H9B . 0.9600 n
  C10 C11 . 1.525(7) n
  C10 H10A . 0.9599 n
  C10 H10B . 0.9599 n
  C11 C17 . 1.535(8) n
  C11 C16 . 1.545(8) n
  C13 H13A . 0.9600 n
  C13 H13B . 0.9600 n
  C13 H13C . 0.9600 n
  C15 H15A . 0.9600 n
  C15 H15B . 0.9600 n
  C15 H15C . 0.9600 n
  C16 H16A . 0.9599 n
  C16 H16B . 0.9600 n
  C16 H16C . 0.9600 n
  C17 H17A . 0.9600 n
  C17 H17B . 0.9600 n
  C17 H17C . 0.9601 n