data_2012879
_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  'epoxy dodecane'
_chemical_formula_moiety  'C16 H24 Cl2 O'
_chemical_formula_sum  'C16 H24 Cl2 O'
_chemical_formula_weight  303.24
_chemical_melting_point  410
_symmetry_cell_setting  'Orthorhombic'
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P_2ac_2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  8.60890(10)
_cell_length_b  13.2050(2)
_cell_length_c  13.9083(2)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1581.10(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.274
_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 -0.07673(13) 0.61167(8) 0.18809(6) 0.0672(4) Uani d . 1 . . Cl
  Cl2 -0.19468(11) 0.72744(9) 0.34664(9) 0.0728(4) Uani d . 1 . . Cl
  O12 -0.0974(3) 0.4277(2) 0.35308(18) 0.0580(7) Uani d . 1 . . O
  C1 0.1587(4) 0.5142(2) 0.33856(19) 0.0370(6) Uani d . 1 . . C
  H1 0.1593 0.5170 0.2696 0.044 Uiso d R 1 . . H
  C2 0.0656(5) 0.4230(2) 0.3707(2) 0.0458(8) Uani d . 1 . . C
  H2 0.1268 0.3629 0.3624 0.055 Uiso d R 1 . . H
  C3 -0.0425(5) 0.4259(2) 0.4513(2) 0.0507(8) Uani d . 1 . . C
  C4 -0.0733(5) 0.5245(3) 0.5032(2) 0.0534(8) Uani d . 1 . . C
  H4A -0.0625 0.5141 0.5712 0.064 Uiso d R 1 . . H
  H4B -0.1772 0.5465 0.4892 0.064 Uiso d R 1 . . H
  C5 0.0359(4) 0.6117(2) 0.4757(2) 0.0395(6) Uani d . 1 . . C
  H5A -0.0144 0.6742 0.4921 0.047 Uiso d R 1 . . H
  H5B 0.1290 0.6045 0.5131 0.047 Uiso d R 1 . . H
  C6 0.0783(3) 0.61160(19) 0.36993(18) 0.0315(5) Uani d . 1 . . C
  C7 0.1274(4) 0.7099(2) 0.3180(2) 0.0379(6) Uani d . 1 . . C
  C8 0.2520(4) 0.7001(3) 0.2432(2) 0.0463(7) Uani d . 1 . . C
  H8A 0.2571 0.7619 0.2071 0.056 Uiso d R 1 . . H
  H8B 0.2266 0.6451 0.2009 0.056 Uiso d R 1 . . H
  C9 0.4118(4) 0.6816(3) 0.2885(3) 0.0597(10) Uani d . 1 . . C
  H9A 0.4582 0.7446 0.3077 0.072 Uiso d R 1 . . H
  H9B 0.4773 0.6488 0.2422 0.072 Uiso d R 1 . . H
  C10 0.4114(4) 0.6128(3) 0.3756(3) 0.0532(8) Uani d . 1 . . C
  H10A 0.5183 0.6048 0.3935 0.064 Uiso d R 1 . . H
  H10B 0.3580 0.6509 0.4242 0.064 Uiso d R 1 . . H
  C11 0.3348(4) 0.5070(3) 0.3677(3) 0.0511(8) Uani d . 1 . . C
  C13 -0.0791(8) 0.3298(3) 0.5051(3) 0.0798(15) Uani d . 1 . . C
  H13A -0.0406 0.3332 0.5698 0.096 Uiso d R 1 . . H
  H13B -0.1898 0.3211 0.5062 0.096 Uiso d R 1 . . H
  H13C -0.0322 0.2736 0.4724 0.096 Uiso d R 1 . . H
  C14 -0.0295(4) 0.6648(2) 0.3005(2) 0.0420(7) Uani d . 1 . . C
  C15 0.1385(5) 0.8090(2) 0.3737(3) 0.0534(9) Uani d . 1 . . C
  H15A 0.1705 0.8624 0.3312 0.064 Uiso d R 1 . . H
  H15B 0.0388 0.8251 0.4006 0.064 Uiso d R 1 . . H
  H15C 0.2132 0.8019 0.4246 0.064 Uiso d R 1 . . H
  C16 0.4199(6) 0.4419(4) 0.2923(5) 0.0875(15) Uani d . 1 . . C
  H16A 0.5281 0.4351 0.3078 0.105 Uiso d R 1 . . H
  H16B 0.3733 0.3760 0.2884 0.105 Uiso d R 1 . . H
  H16C 0.4093 0.4758 0.2316 0.105 Uiso d R 1 . . H
  C17 0.3586(6) 0.4536(3) 0.4648(3) 0.0730(13) Uani d . 1 . . C
  H17A 0.4674 0.4494 0.4794 0.088 Uiso d R 1 . . H
  H17B 0.3075 0.4940 0.5127 0.088 Uiso d R 1 . . H
  H17C 0.3145 0.3868 0.4644 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 0.0750(7) 0.0783(6) 0.0484(5) -0.0221(5) -0.0290(5) 0.0076(4)
  Cl2 0.0385(5) 0.0754(7) 0.1045(9) 0.0155(4) 0.0004(5) 0.0154(6)
  O12 0.0684(16) 0.0561(14) 0.0494(12) -0.0272(12) -0.0011(13) -0.0044(11)
  C1 0.0488(15) 0.0294(11) 0.0329(13) -0.0016(12) 0.0040(11) -0.0027(10)
  C2 0.063(2) 0.0311(13) 0.0434(15) -0.0060(14) 0.0072(15) -0.0045(11)
  C3 0.071(2) 0.0387(15) 0.0429(15) -0.0152(15) 0.0077(16) 0.0010(12)
  C4 0.069(2) 0.0486(16) 0.0425(15) -0.0064(16) 0.0164(17) -0.0020(13)
  C5 0.0510(16) 0.0338(12) 0.0339(12) -0.0005(13) 0.0029(12) -0.0071(10)
  C6 0.0326(12) 0.0292(11) 0.0327(12) -0.0002(10) -0.0039(10) -0.0009(9)
  C7 0.0403(14) 0.0309(12) 0.0426(13) -0.0033(11) -0.0089(12) 0.0073(12)
  C8 0.0459(16) 0.0464(15) 0.0467(15) -0.0086(14) 0.0008(13) 0.0113(13)
  C9 0.0397(16) 0.065(2) 0.074(2) -0.0079(16) 0.0037(17) 0.0174(19)
  C10 0.0358(14) 0.0560(18) 0.068(2) 0.0007(15) -0.0101(15) 0.0128(17)
  C11 0.0486(18) 0.0429(15) 0.062(2) 0.0134(14) 0.0009(15) 0.0038(14)
  C13 0.126(4) 0.0463(18) 0.068(2) -0.022(2) 0.028(3) 0.0080(16)
  C14 0.0383(14) 0.0428(14) 0.0451(15) -0.0015(12) -0.0090(13) 0.0055(13)
  C15 0.066(2) 0.0271(12) 0.067(2) -0.0040(14) -0.0132(18) -0.0004(13)
  C16 0.072(3) 0.081(3) 0.109(4) 0.024(3) 0.023(3) -0.020(3)
  C17 0.072(3) 0.058(2) 0.089(3) 0.016(2) -0.015(2) 0.029(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
  Cl1 C14 . 1.761(3) ?
  Cl2 C14 . 1.766(3) ?
  O12 C2 . 1.426(5) y
  O12 C3 . 1.446(4) y
  C1 C2 . 1.514(4) y
  C1 C6 . 1.525(4) y
  C1 C11 . 1.572(4) y
  C1 H1 . 0.9600 ?
  C2 C3 . 1.457(5) y
  C2 H2 . 0.9599 ?
  C3 C13 . 1.506(4) ?
  C3 C4 . 1.512(4) ?
  C4 C5 . 1.536(5) ?
  C4 H4A . 0.9602 ?
  C4 H4B . 0.9601 ?
  C5 C6 . 1.515(4) ?
  C5 H5A . 0.9599 ?
  C5 H5B . 0.9600 ?
  C6 C14 . 1.513(4) y
  C6 C7 . 1.544(4) y
  C7 C14 . 1.496(4) y
  C7 C8 . 1.500(4) ?
  C7 C15 . 1.524(4) ?
  C8 C9 . 1.533(5) ?
  C8 H8A . 0.9601 ?
  C8 H8B . 0.9600 ?
  C9 C10 . 1.513(5) ?
  C9 H9A . 0.9600 ?
  C9 H9B . 0.9600 ?
  C10 C11 . 1.549(5) ?
  C10 H10A . 0.9598 ?
  C10 H10B . 0.9599 ?
  C11 C17 . 1.537(5) ?
  C11 C16 . 1.541(5) ?
  C13 H13A . 0.9600 ?
  C13 H13B . 0.9600 ?
  C13 H13C . 0.9600 ?
  C15 H15A . 0.9600 ?
  C15 H15B . 0.9599 ?
  C15 H15C . 0.9601 ?
  C16 H16A . 0.9600 ?
  C16 H16B . 0.9599 ?
  C16 H16C . 0.9600 ?
  C17 H17A . 0.9601 ?
  C17 H17B . 0.9600 ?
  C17 H17C . 0.9601 ?