(1S,3R,8S,9S,10R)-2,2-Dichloro-9,10-epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodecane and (1S,3R,8S,10R)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodecan-9-one

The stereochemistries of the title compounds, both C₁₆H₂₄Cl₂O, have been established by X-ray diffraction. In both structures, the seven-membered ring adopts the same conformation, whereas the six-membered ring shows an envelope conformation in the epoxy­do­decane structure and a boat conformation in the dodecan-9-one structure.

S1. Comment

With the aim of developing the Moroccan floral inheritance, in particular plants which contain essential oils, we have directed our research endeavours towards the oil of the Atlas cedar (Cedrus atlantica), the main constituent of which is β-himachalene, (I) (Plattier & Teisseire, 1974). The reactivity of this sesquiterpene has been extensively studied by our group (Benharref et al., 1991; Chekroun et al., 2000; El Jamili et al., 2001; Auhmani et al., 2002) in order to prepare new products having olfactive properties suitable for the perfume or cosmetics industry.

The action of dichlorocarbene on (I) leads to (1S,3R,8S)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-9-ene, (II), the structure of which was determined by Auhmani et al. (1999). The treatment of (II) by m-chloroperbenzoic acid (m-CPBA) gives a mixture of two epoxides, the first title compound (1S,3R,8S,9S,10R)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]- 9,10-epoxydodecane, (III), and (IV), with a yield of 80% in the ratio 30:70. The ¹H and ¹³C NMR spectra of (III) and (IV) are almost similar and this prevents the determination of their structures. In the presence of BF₃—Et₂O, compound (IV) rearranges to the second title compound, (1S,3R,8S,10R)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec- 9-one, (V), in a moderate yield of 60%. A spectroscopic analysis by NMR with high mono- and bidimensional resolution confirmed the rearrangement of the epoxide into a ketone. \sch

The absolute structure of the himachalene core has been investigated previously (Joseph & Dev, 1968; Chiaroni et al., 1996). The structure determination of compounds (III) and (V) (Figs. 1 and 2, respectively) now allows us to assign the stereochemistry of the cyclopropane bridges in positions 6 and 7 for compounds (III), (IV) and (V), and of the epoxides for compounds (III) and (IV). The following configurations have been found: RSRSR and RRSSR for atoms C1/C2/C3/C6/C7 in (III) and (IV), respectively, and RRSR for atoms C1/C3/C6/C7 in (V).

The bond lengths and angles in (III) and (V) (Tables 1 and 2) are similar to those found in related molecules (Lassaba et al., 1997; Auhmani et al., 2000), except for the C1—C11 bond which is, in both cases, rather long, being 1.572 (4) Å in (III) and 1.590 (5) Å in (V). The core of the molecule consists of a six- and seven-membered fused ring system. In both structures, the seven-membered ring adopts the same conformation composed of three relatively planar fragments, namely C1/C6/C7/C8 (plane 1), C1/C8/C9/C11 (plane 2) and C9/C10/C11 (plane 3). The dihedral angle between planes 1 and 2 is 60.8 (3)° in (III) and 57.9 (3)° in (V), while that between planes 2 and 3 is 50.0 (3)° in (III) and 52.4 (3)° in (V). The six-membered ring adopts an envelope conformation in (III) [atom C6 is 0.619 (3) Å from the C1—C6 plane] but a boat conformation in (V) [atom C1 is 0.522 (4) Å and atom C4 is -0.667 (5) Å from the C2/C3/C5/C6 plane]. The cyclopropane bridge shares a common atom, C6, with the two rings of the molecule and, in the case of (III), is in a cis conformation with respect to the epoxide.

S2. Experimental

For the synthesis of compound (II), potassium tert-butylate (4 g, 35 mmol) was added to a solution of β-himachalene, (I) (2 g, 9.7 mmole), in hexane (60 ml) at 273 K. The mixture was stirred for 10 min and then a stoichiometric quantity of CHCl₃ was added dropwise over 30 min. The reaction mixture was stirred for 8 h. After hydrolysis with water (20 ml), the organic phase was extracted with ether, washed with water, dried and concentrated. Chromatography of the residue obtained on silica gel gave (II) in a yield of 50%. For the epoxidation of (II), to a 100 ml flask containing (II) (500 mg, 1.74 mmol) solubilized in CH₂Cl₂ (30 ml), a stochiometric quantity of m-chloroperbenzoic acid (m-CPBA) was added. The reaction mixture was stirred at ambient temperature for 2 h, then treated with a 10% solution of sodium dihydrogenocarbonate. The aqueous phase was extracted with ether, and the organic phases were dried and concentrated. Silica-gel chromatography of the reaction mixture residue allowed isolation of epoxides (III) and (IV) in a pure state (m.p. 409–410 K). Crystallization was carried out at room temperature from a hexane solution. To obtain compound (V), BF₃—Et₂O (0.2 ml) was added dropwise to a solution of (IV) (200 mg, 0.66 mmol) in CH₂Cl₂ (20 ml) at 195 K under N₂. The reaction mixture was stirred for 90 min at a constant temperature of 195 K and then left at ambient temperature for 24 h. Water (20 ml) was then added in order to separate the two phases, and the organic phase was dried and concentrated. Silica-gel chromatography of the reaction mixture product gave (V) in a yield of 60% (m.p. 362–363 K). Crystallization was carried out at room temperature from a hexane solution.

S3. Refinement

Friedel pairs were merged prior to refinement. H atoms were placed geometrically and treated as riding, with C—H = 0.96 Å. Is this added text OK?

Computing details

For both compounds, data collection: KappaCCD Server Software (Nonius, 1998) and maXus (Mackay et al., 1999); cell refinement: Please provide missing details; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The molecular structure of (V), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

(III) (1S,3R,8S,9S,10R)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]- 9,10-epoxydodecane

Crystal data

C16H24Cl2O	Dx = 1.274 Mg m^−3
Mr = 303.24	Melting point: 410 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P_2ac_2ab	Cell parameters from 22257 reflections
a = 8.6089 (1) Å	θ = 2.0–26.4°
b = 13.2050 (2) Å	µ = 0.40 mm^−1
c = 13.9083 (2) Å	T = 293 K
V = 1581.10 (4) Å^3	Prism, colourless
Z = 4	0.35 × 0.25 × 0.25 mm
F(000) = 648

Data collection

Nonius KappaCCD area-detector diffractometer	1749 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 26.4°, θmin = 2.1°
ϕ scans	h = 0→10
22257 measured reflections	k = 0→16
1821 independent reflections	l = 0→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.166	w = 1/[σ^2(Fo^2) + (0.1188P)^2 + 0.2141P] where P = (Fo^2 + 2Fc^2)/3
S = 1.20	(Δ/σ)max < 0.001
1821 reflections	Δρmax = 0.36 e Å^−3
172 parameters	Δρmin = −0.50 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.30 (12)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	−0.07673 (13)	0.61167 (8)	0.18809 (6)	0.0672 (4)
Cl2	−0.19468 (11)	0.72744 (9)	0.34664 (9)	0.0728 (4)
O12	−0.0974 (3)	0.4277 (2)	0.35308 (18)	0.0580 (7)
C1	0.1587 (4)	0.5142 (2)	0.33856 (19)	0.0370 (6)
H1	0.1593	0.5170	0.2696	0.044*
C2	0.0656 (5)	0.4230 (2)	0.3707 (2)	0.0458 (8)
H2	0.1268	0.3629	0.3624	0.055*
C3	−0.0425 (5)	0.4259 (2)	0.4513 (2)	0.0507 (8)
C4	−0.0733 (5)	0.5245 (3)	0.5032 (2)	0.0534 (8)
H4A	−0.0625	0.5141	0.5712	0.064*
H4B	−0.1772	0.5465	0.4892	0.064*
C5	0.0359 (4)	0.6117 (2)	0.4757 (2)	0.0395 (6)
H5A	−0.0144	0.6742	0.4921	0.047*
H5B	0.1290	0.6045	0.5131	0.047*
C6	0.0783 (3)	0.61160 (19)	0.36993 (18)	0.0315 (5)
C7	0.1274 (4)	0.7099 (2)	0.3180 (2)	0.0379 (6)
C8	0.2520 (4)	0.7001 (3)	0.2432 (2)	0.0463 (7)
H8A	0.2571	0.7619	0.2071	0.056*
H8B	0.2266	0.6451	0.2009	0.056*
C9	0.4118 (4)	0.6816 (3)	0.2885 (3)	0.0597 (10)
H9A	0.4582	0.7446	0.3077	0.072*
H9B	0.4773	0.6488	0.2422	0.072*
C10	0.4114 (4)	0.6128 (3)	0.3756 (3)	0.0532 (8)
H10A	0.5183	0.6048	0.3935	0.064*
H10B	0.3580	0.6509	0.4242	0.064*
C11	0.3348 (4)	0.5070 (3)	0.3677 (3)	0.0511 (8)
C13	−0.0791 (8)	0.3298 (3)	0.5051 (3)	0.0798 (15)
H13A	−0.0406	0.3332	0.5698	0.096*
H13B	−0.1898	0.3211	0.5062	0.096*
H13C	−0.0322	0.2736	0.4724	0.096*
C14	−0.0295 (4)	0.6648 (2)	0.3005 (2)	0.0420 (7)
C15	0.1385 (5)	0.8090 (2)	0.3737 (3)	0.0534 (9)
H15A	0.1705	0.8624	0.3312	0.064*
H15B	0.0388	0.8251	0.4006	0.064*
H15C	0.2132	0.8019	0.4246	0.064*
C16	0.4199 (6)	0.4419 (4)	0.2923 (5)	0.0875 (15)
H16A	0.5281	0.4351	0.3078	0.105*
H16B	0.3733	0.3760	0.2884	0.105*
H16C	0.4093	0.4758	0.2316	0.105*
C17	0.3586 (6)	0.4536 (3)	0.4648 (3)	0.0730 (13)
H17A	0.4674	0.4494	0.4794	0.088*
H17B	0.3075	0.4940	0.5127	0.088*
H17C	0.3145	0.3868	0.4644	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	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)

Geometric parameters (Å, º)

Cl1—C14	1.761 (3)	C8—C9	1.533 (5)
Cl2—C14	1.766 (3)	C8—H8A	0.9601
O12—C2	1.426 (5)	C8—H8B	0.9600
O12—C3	1.446 (4)	C9—C10	1.513 (5)
C1—C2	1.514 (4)	C9—H9A	0.9600
C1—C6	1.525 (4)	C9—H9B	0.9600
C1—C11	1.572 (4)	C10—C11	1.549 (5)
C1—H1	0.9600	C10—H10A	0.9598
C2—C3	1.457 (5)	C10—H10B	0.9599
C2—H2	0.9599	C11—C17	1.537 (5)
C3—C13	1.506 (4)	C11—C16	1.541 (5)
C3—C4	1.512 (4)	C13—H13A	0.9600
C4—C5	1.536 (5)	C13—H13B	0.9600
C4—H4A	0.9602	C13—H13C	0.9600
C4—H4B	0.9601	C15—H15A	0.9600
C5—C6	1.515 (4)	C15—H15B	0.9599
C5—H5A	0.9599	C15—H15C	0.9601
C5—H5B	0.9600	C16—H16A	0.9600
C6—C14	1.513 (4)	C16—H16B	0.9599
C6—C7	1.544 (4)	C16—H16C	0.9600
C7—C14	1.496 (4)	C17—H17A	0.9601
C7—C8	1.500 (4)	C17—H17B	0.9600
C7—C15	1.524 (4)	C17—H17C	0.9601
C2—O12—C3	61.0 (2)	C10—C9—C8	115.0 (3)
C2—C1—C6	110.3 (2)	C10—C9—H9A	107.4
C2—C1—C11	112.7 (3)	C8—C9—H9A	110.4
C6—C1—C11	114.5 (2)	C10—C9—H9B	105.5
C2—C1—H1	109.2	C8—C9—H9B	108.8
C6—C1—H1	104.8	H9A—C9—H9B	109.5
C11—C1—H1	104.8	C9—C10—C11	119.1 (3)
O12—C2—C3	60.2 (2)	C9—C10—H10A	105.8
O12—C2—C1	115.8 (3)	C11—C10—H10A	109.1
C3—C2—C1	123.0 (3)	C9—C10—H10B	104.5
O12—C2—H2	123.7	C11—C10—H10B	108.6
C3—C2—H2	117.7	H10A—C10—H10B	109.5
C1—C2—H2	109.4	C17—C11—C16	106.2 (4)
O12—C3—C2	58.8 (2)	C17—C11—C10	107.1 (3)
O12—C3—C13	114.5 (3)	C16—C11—C10	110.4 (4)
C2—C3—C13	119.6 (3)	C17—C11—C1	112.5 (3)
O12—C3—C4	112.3 (3)	C16—C11—C1	108.5 (3)
C2—C3—C4	120.1 (3)	C10—C11—C1	112.0 (2)
C13—C3—C4	116.8 (3)	C3—C13—H13A	110.7
C3—C4—C5	114.8 (3)	C3—C13—H13B	108.5
C3—C4—H4A	109.3	H13A—C13—H13B	109.5
C5—C4—H4A	107.0	C3—C13—H13C	109.2
C3—C4—H4B	109.1	H13A—C13—H13C	109.5
C5—C4—H4B	107.0	H13B—C13—H13C	109.5
H4A—C4—H4B	109.5	C7—C14—C6	61.74 (18)
C6—C5—C4	112.9 (2)	C7—C14—Cl1	120.8 (3)
C6—C5—H5A	109.9	C6—C14—Cl1	121.5 (2)
C4—C5—H5A	108.0	C7—C14—Cl2	118.8 (2)
C6—C5—H5B	109.0	C6—C14—Cl2	118.7 (2)
C4—C5—H5B	107.5	Cl1—C14—Cl2	108.87 (17)
H5A—C5—H5B	109.5	C7—C15—H15A	109.6
C14—C6—C5	118.1 (3)	C7—C15—H15B	109.3
C14—C6—C1	119.2 (2)	H15A—C15—H15B	109.5
C5—C6—C1	112.8 (2)	C7—C15—H15C	109.4
C14—C6—C7	58.60 (18)	H15A—C15—H15C	109.5
C5—C6—C7	121.2 (2)	H15B—C15—H15C	109.5
C1—C6—C7	116.8 (2)	C11—C16—H16A	111.1
C14—C7—C8	119.9 (3)	C11—C16—H16B	110.2
C14—C7—C15	118.8 (3)	H16A—C16—H16B	109.5
C8—C7—C15	112.4 (3)	C11—C16—H16C	107.1
C14—C7—C6	59.66 (18)	H16A—C16—H16C	109.5
C8—C7—C6	116.6 (2)	H16B—C16—H16C	109.5
C15—C7—C6	120.1 (3)	C11—C17—H17A	110.0
C7—C8—C9	111.7 (3)	C11—C17—H17B	107.1
C7—C8—H8A	108.9	H17A—C17—H17B	109.5
C9—C8—H8A	108.0	C11—C17—H17C	111.3
C7—C8—H8B	109.1	H17A—C17—H17C	109.5
C9—C8—H8B	109.6	H17B—C17—H17C	109.5
H8A—C8—H8B	109.4

(V) (1S,3R,8S,10R)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec- 9-one

Crystal data

C16H24Cl2O	F(000) = 324
Mr = 303.24	Dx = 1.232 Mg m^−3
Monoclinic, P21	Melting point: 363 K
Hall symbol: P_2yb	Mo Kα radiation, λ = 0.71073 Å
a = 8.9545 (4) Å	Cell parameters from 4965 reflections
b = 10.6231 (6) Å	θ = 1.0–25.1°
c = 9.0858 (6) Å	µ = 0.39 mm^−1
β = 109.497 (4)°	T = 293 K
V = 814.78 (8) Å^3	Needle, colourless
Z = 2	0.40 × 0.25 × 0.20 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1392 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
Graphite monochromator	θmax = 25.1°, θmin = 3.1°
ϕ scans	h = 0→10
4965 measured reflections	k = 0→12
1427 independent reflections	l = −11→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.164	w = 1/[σ^2(Fo^2) + (0.1024P)^2 + 0.181P] where P = (Fo^2 + 2Fc^2)/3
S = 1.23	(Δ/σ)max < 0.001
1427 reflections	Δρmax = 0.55 e Å^−3
172 parameters	Δρmin = −0.67 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (13)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.87348 (17)	0.45555 (10)	0.11114 (18)	0.0659 (5)
Cl2	0.98526 (18)	0.26217 (14)	−0.04459 (15)	0.0694 (5)
O12	0.9920 (6)	0.3241 (5)	0.5582 (5)	0.0799 (13)
C1	0.8097 (4)	0.2435 (4)	0.3241 (4)	0.0382 (8)
H1	0.7781	0.3303	0.3118	0.046*
C2	0.9650 (5)	0.2411 (5)	0.4619 (4)	0.0475 (10)
C3	1.0803 (5)	0.1338 (5)	0.4744 (5)	0.0535 (12)
H3	1.0390	0.0629	0.5139	0.064*
C4	1.0916 (5)	0.0988 (5)	0.3167 (6)	0.0563 (12)
H4A	1.1414	0.1669	0.2813	0.068*
H4B	1.1539	0.0239	0.3261	0.068*
C5	0.9296 (5)	0.0769 (4)	0.1953 (5)	0.0457 (9)
H5A	0.9433	0.0549	0.0982	0.055*
H5B	0.8773	0.0093	0.2287	0.055*
C6	0.8326 (5)	0.1967 (4)	0.1744 (4)	0.0363 (8)
C7	0.7003 (5)	0.2271 (5)	0.0194 (5)	0.0501 (10)
C8	0.5582 (6)	0.2983 (6)	0.0303 (7)	0.0694 (15)
H8A	0.5943	0.3689	0.0990	0.083*
H8B	0.4952	0.3278	−0.0714	0.083*
C9	0.4525 (6)	0.2185 (8)	0.0933 (7)	0.0780 (18)
H9A	0.3921	0.2718	0.1376	0.094*
H9B	0.3818	0.1697	0.0100	0.094*
C10	0.5414 (7)	0.1263 (7)	0.2240 (7)	0.0727 (16)
H10A	0.4687	0.0832	0.2639	0.087*
H10B	0.5954	0.0661	0.1809	0.087*
C11	0.6695 (5)	0.1791 (5)	0.3672 (5)	0.0504 (11)
C13	1.2398 (7)	0.1615 (8)	0.5996 (8)	0.086 (2)
H13A	1.3118	0.0930	0.6067	0.104*
H13B	1.2255	0.1734	0.6989	0.104*
H13C	1.2822	0.2370	0.5710	0.104*
C14	0.8573 (5)	0.2942 (4)	0.0623 (5)	0.0457 (9)
C15	0.6588 (9)	0.1317 (7)	−0.1114 (6)	0.0787 (19)
H15A	0.5746	0.1645	−0.1990	0.094*
H15B	0.6245	0.0555	−0.0759	0.094*
H15C	0.7494	0.1145	−0.1422	0.094*
C16	0.6035 (10)	0.2806 (8)	0.4507 (10)	0.089 (2)
H16A	0.5184	0.2452	0.4793	0.106*
H16B	0.5643	0.3493	0.3797	0.106*
H16C	0.6846	0.3105	0.5427	0.106*
C17	0.7252 (8)	0.0713 (7)	0.4854 (7)	0.0730 (16)
H17A	0.6351	0.0368	0.5061	0.088*
H17B	0.7999	0.1024	0.5808	0.088*
H17C	0.7742	0.0069	0.4431	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	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)

Geometric parameters (Å, º)

Cl1—C14	1.764 (5)	C8—H8A	0.9600
Cl2—C14	1.765 (5)	C8—H8B	0.9601
O12—C2	1.208 (6)	C9—C10	1.540 (9)
C1—C2	1.530 (5)	C9—H9A	0.9599
C1—C6	1.525 (5)	C9—H9B	0.9600
C1—C11	1.590 (5)	C10—C11	1.525 (7)
C1—H1	0.9601	C10—H10A	0.9599
C2—C3	1.517 (7)	C10—H10B	0.9599
C3—C4	1.516 (7)	C11—C17	1.535 (8)
C3—C13	1.528 (6)	C11—C16	1.545 (8)
C3—H3	0.9600	C13—H13A	0.9600
C4—C5	1.519 (6)	C13—H13B	0.9600
C4—H4A	0.9600	C13—H13C	0.9600
C4—H4B	0.9600	C15—H15A	0.9600
C5—C6	1.516 (5)	C15—H15B	0.9600
C5—H5A	0.9600	C15—H15C	0.9600
C5—H5B	0.9600	C16—H16A	0.9599
C6—C14	1.520 (5)	C16—H16B	0.9600
C6—C7	1.543 (5)	C16—H16C	0.9600
C7—C14	1.507 (6)	C17—H17A	0.9600
C7—C15	1.511 (8)	C17—H17B	0.9600
C7—C8	1.512 (8)	C17—H17C	0.9601
C8—C9	1.518 (9)
C6—C1—C2	111.6 (3)	C10—C9—H9A	105.7
C6—C1—C11	115.6 (3)	C8—C9—H9B	109.5
C2—C1—C11	111.6 (3)	C10—C9—H9B	107.5
C6—C1—H1	109.4	H9A—C9—H9B	109.5
C2—C1—H1	105.2	C11—C10—C9	118.2 (6)
C11—C1—H1	102.4	C11—C10—H10A	105.4
O12—C2—C3	121.9 (4)	C9—C10—H10A	110.7
O12—C2—C1	119.2 (5)	C11—C10—H10B	104.8
C3—C2—C1	118.9 (4)	C9—C10—H10B	108.0
C4—C3—C2	111.8 (3)	H10A—C10—H10B	109.5
C4—C3—C13	114.2 (5)	C10—C11—C17	107.4 (5)
C2—C3—C13	110.7 (5)	C10—C11—C16	112.0 (5)
C4—C3—H3	108.5	C17—C11—C16	105.4 (5)
C2—C3—H3	106.3	C10—C11—C1	112.3 (4)
C13—C3—H3	104.7	C17—C11—C1	113.2 (4)
C3—C4—C5	112.0 (4)	C16—C11—C1	106.5 (4)
C3—C4—H4A	108.5	C3—C13—H13A	110.1
C5—C4—H4A	108.1	C3—C13—H13B	109.9
C3—C4—H4B	109.9	H13A—C13—H13B	109.5
C5—C4—H4B	108.9	C3—C13—H13C	108.4
H4A—C4—H4B	109.5	H13A—C13—H13C	109.5
C6—C5—C4	109.3 (4)	H13B—C13—H13C	109.5
C6—C5—H5A	109.5	C7—C14—C6	61.3 (3)
C4—C5—H5A	108.7	C7—C14—Cl1	121.1 (3)
C6—C5—H5B	110.4	C6—C14—Cl1	120.8 (3)
C4—C5—H5B	109.5	C7—C14—Cl2	119.1 (3)
H5A—C5—H5B	109.5	C6—C14—Cl2	120.2 (3)
C5—C6—C14	116.8 (4)	Cl1—C14—Cl2	108.2 (2)
C5—C6—C1	113.8 (3)	C7—C15—H15A	109.1
C14—C6—C1	117.9 (3)	C7—C15—H15B	108.9
C5—C6—C7	121.6 (4)	H15A—C15—H15B	109.5
C14—C6—C7	58.9 (3)	C7—C15—H15C	110.4
C1—C6—C7	117.1 (3)	H15A—C15—H15C	109.5
C14—C7—C15	119.0 (5)	H15B—C15—H15C	109.5
C14—C7—C8	118.7 (4)	C11—C16—H16A	109.2
C15—C7—C8	113.3 (5)	C11—C16—H16B	108.4
C14—C7—C6	59.8 (3)	H16A—C16—H16B	109.5
C15—C7—C6	119.3 (4)	C11—C16—H16C	110.9
C8—C7—C6	116.9 (4)	H16A—C16—H16C	109.5
C7—C8—C9	112.9 (5)	H16B—C16—H16C	109.5
C7—C8—H8A	109.0	C11—C17—H17A	108.9
C9—C8—H8A	107.9	C11—C17—H17B	109.9
C7—C8—H8B	109.7	H17A—C17—H17B	109.5
C9—C8—H8B	107.8	C11—C17—H17C	109.6
H8A—C8—H8B	109.5	H17A—C17—H17C	109.5
C8—C9—C10	114.8 (4)	H17B—C17—H17C	109.5
C8—C9—H9A	109.7