(1S,3S,8R,9S,11R)-10,10-Di­chloro-3,7,7,11-tetra­methyl­tetra­cyclo[6.5.0.01,3.09,11]trideca­ne

Benharref, A.; Ourhriss, N.; El Ammari, L.; Saadi, M.; Berraho, M.

doi:10.1107/S1600536813013457

(1S,3S,8R,9S,11R)-10,10-Dichloro-3,7,7,11-tetramethyltetracyclo[6.5.0.0^1,3.0^9,11]tridecane

A. Benharref, N. Ourhriss, L. El Ammari, M. Saadi and M. Berraho

The title compound, C₁₇H₂₆Cl₂, was synthesized from β-himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The asymmetric unit contains two independent molecules with similar conformations. Each molecule is built up from fused six- and seven-membered rings and two three-membered rings from the reaction of β-himachalene with dichlorocarbene. In both molecules, the six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. The absolute configuration was established from anomalous dispersion effects.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813013457/rz5066sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536813013457/rz5066Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813013457/rz5066Isup3.cml Supplementary material

CCDC reference: 955081

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.050
wR factor = 0.123
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......      0.962
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0055 Ang
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H26    ..  H33A    ..       1.89 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.071
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          4
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         74
PLAT915_ALERT_3_C Low Friedel Pair Coverage ......................         64 %

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT791_ALERT_4_G Note: The Model has Chirality at C1     (Verify)          S
PLAT791_ALERT_4_G Note: The Model has Chirality at C3     (Verify)          S
PLAT791_ALERT_4_G Note: The Model has Chirality at C8     (Verify)          R
PLAT791_ALERT_4_G Note: The Model has Chirality at C9     (Verify)          S
PLAT791_ALERT_4_G Note: The Model has Chirality at C11    (Verify)          R
PLAT791_ALERT_4_G Note: The Model has Chirality at C18    (Verify)          S
PLAT791_ALERT_4_G Note: The Model has Chirality at C20    (Verify)          S
PLAT791_ALERT_4_G Note: The Model has Chirality at C25    (Verify)          R
PLAT791_ALERT_4_G Note: The Model has Chirality at C26    (Verify)          S
PLAT791_ALERT_4_G Note: The Model has Chirality at C28    (Verify)          R
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         61
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......          !

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  13 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

The essential oil of the Alas cedar (Cedrus atlantica) consist mainly (50%) of a bicyclic hydrocarbon called β-himachalene. The reactivity of this sesquiterpene and its derivatives has been studied extensively by our team (Ourhriss et al., 2013; Oukhrib et al.,2013) in order to prepare new products having biological proprieties (El Haib et al., 2011). In this work we present the crystal structure of the title compound, (1S,3S,8R,9S,11R)-10,10-dichloro-3,7,7,11-tetramethyltetracyclo-[6.5.0.0^1,3.0^9,11]tridecane.

The asymmetric unit of the title compound contains two independent molecules of similar geometry (Fig. 1). Each molecule contains a fused six- and a seven-membered rings, which is fused to two three-membered rings. The six-membered ring has a half chair conformation, as indicated by the total puckering amplitude QT = 0.492 (4) Å and spherical polar angle θ = 136.8 (5)° with ϕ = 131.0 (6)°, whereas the seven-membered ring displays a boat conformation with QT = 1.1447 (5) Å, θ = 88.47 (2)°, ϕ2 = -49.96 (2)° and ϕ3 = -147.50 (9)° (Cremer & Pople, 1975). Owing to the presence of Cl atoms, the absolute configuration could be fully confirmed by refining the Flack parameter (Flack & Bernardinelli, 2000) as C1(S), C3(R), C8(R), C9(S) and C11(R).

Related literature top

For the reactivity and biological properties of β-himachalene, see: El Haib et al. (2011); El Jamili et al. (2002); Auhmani et al. (2002). For related structures, see: Oukhrib et al. (2013); Ourhriss et al. (2013). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

In a three-necked flask equipped with a dropping funnel, a condenser and a magnetic stirrer, maintained at 0°C, 2 g of ( 1S,3R,8R)-2,2-dichloro-3,7,7,10 tetramethyltricyclo[6.4.0.0¹,³]dodec-9-ene (El Jamili et al., 2002) were introduced in 50 ml of ether. Thereafter and simultaneously 7 g of sodium were added by small portions during one hour, and dropwise 65 ml of a methanol solution 2.5% of water. The reaction mixture was stirred for 12 h. After hydrolysis with 20 ml of water, the two phases were separated and the aqueous phase extracted three times with 20 ml of ether. The organic phases were combined and dried over sodium sulfate and concentrated. The residue obtained was chromatographed on a silica column with hexane as eluent to give the sesquiterpene hydrocarbon (1S,3S,8R,9S,11R)-3,7,7,11-tetramethyltricyclo-[6.5.0.⁰1,3]tridec-9-ene) with a yield of 90%. The treatment of this sesquiterpene with two equivalents of N-bromosuccinimide (NBS) (Auhmani et al., 2002) gave the title compound with a yield of 80%. Crystals of the title compound suitable for X-ray analysis were recrystallized from pentane.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

(1S,3S,8R,9S,11R)-10,10-Dichloro-3,7,7,11-tetramethyltetracyclo[6.5.0.0^1,3.0^9,11]tridecane top

Crystal data top

C₁₇H₂₆Cl₂	F(000) = 648
M_r = 301.28	D_x = 1.222 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5832 reflections
a = 6.4930 (2) Å	θ = 2.8–27.1°
b = 29.0000 (8) Å	µ = 0.38 mm⁻¹
c = 9.2854 (4) Å	T = 296 K
β = 110.454 (1)°	Block, colourless
V = 1638.18 (10) Å³	0.45 × 0.35 × 0.30 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5438 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 27.1°, θ_min = 2.8°
ω and ϕ scans	h = −8→8
10017 measured reflections	k = −31→37
5832 independent reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0511P)² + 0.9439P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
5832 reflections	Δρ_max = 0.29 e Å⁻³
343 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack & Bernardinelli (2000), 1283 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (6)

Crystal data top

C₁₇H₂₆Cl₂	V = 1638.18 (10) Å³
M_r = 301.28	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 6.4930 (2) Å	µ = 0.38 mm⁻¹
b = 29.0000 (8) Å	T = 296 K
c = 9.2854 (4) Å	0.45 × 0.35 × 0.30 mm
β = 110.454 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5438 reflections with I > 2σ(I)
10017 measured reflections	R_int = 0.021
5832 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.123	Δρ_max = 0.29 e Å⁻³
S = 1.09	Δρ_min = −0.21 e Å⁻³
5832 reflections	Absolute structure: Flack & Bernardinelli (2000), 1283 Friedel pairs
343 parameters	Absolute structure parameter: 0.05 (6)
1 restraint

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1016 (5)	0.68419 (11)	0.5418 (3)	0.0366 (7)
C2	0.2266 (7)	0.63984 (13)	0.6031 (4)	0.0515 (9)
H2A	0.3859	0.6411	0.6410	0.062*
H2B	0.1642	0.6186	0.6574	0.062*
C3	0.1069 (7)	0.64603 (13)	0.4316 (4)	0.0509 (9)
C4	0.2490 (8)	0.65463 (17)	0.3354 (5)	0.0680 (12)
H4A	0.3903	0.6665	0.4011	0.082*
H4B	0.2744	0.6256	0.2926	0.082*
C5	0.1471 (9)	0.68839 (19)	0.2059 (5)	0.0743 (14)
H5A	0.0479	0.6718	0.1184	0.089*
H5B	0.2624	0.7016	0.1750	0.089*
C6	0.0183 (7)	0.72809 (16)	0.2487 (4)	0.0630 (12)
H6A	−0.0360	0.7485	0.1608	0.076*
H6B	−0.1089	0.7147	0.2648	0.076*
C7	0.1415 (6)	0.75762 (13)	0.3903 (4)	0.0450 (8)
C8	0.2305 (4)	0.72854 (10)	0.5441 (3)	0.0328 (6)
H8	0.3810	0.7193	0.5568	0.039*
C9	0.2458 (5)	0.75976 (11)	0.6788 (4)	0.0378 (7)
H9	0.2630	0.7922	0.6560	0.045*
C10	0.3447 (5)	0.74965 (13)	0.8464 (4)	0.0444 (8)
C11	0.0997 (5)	0.75392 (13)	0.7759 (4)	0.0453 (8)
C12	−0.0366 (6)	0.71010 (14)	0.7494 (4)	0.0513 (9)
H12A	−0.1687	0.7160	0.7726	0.062*
H12B	0.0468	0.6864	0.8194	0.062*
C13	−0.1015 (5)	0.69226 (13)	0.5844 (4)	0.0482 (8)
H13A	−0.1825	0.6636	0.5745	0.058*
H13B	−0.1966	0.7145	0.5143	0.058*
C14	−0.0967 (9)	0.61736 (16)	0.3506 (5)	0.0789 (15)
H14A	−0.1805	0.6136	0.4170	0.118*
H14B	−0.0534	0.5876	0.3256	0.118*
H14C	−0.1849	0.6327	0.2579	0.118*
C15	0.3343 (8)	0.78312 (17)	0.3693 (5)	0.0680 (12)
H15A	0.4074	0.8013	0.4591	0.102*
H15B	0.2811	0.8030	0.2812	0.102*
H15C	0.4357	0.7612	0.3542	0.102*
C16	−0.0308 (7)	0.79471 (16)	0.3940 (5)	0.0671 (12)
H16A	−0.1548	0.7798	0.4076	0.101*
H16B	−0.0784	0.8115	0.2990	0.101*
H16C	0.0350	0.8156	0.4777	0.101*
C17	−0.0109 (8)	0.79623 (18)	0.8130 (6)	0.0725 (13)
H17A	−0.1668	0.7943	0.7599	0.109*
H17B	0.0448	0.8235	0.7806	0.109*
H17C	0.0193	0.7977	0.9217	0.109*
C18	0.6936 (5)	0.51198 (11)	0.7358 (3)	0.0344 (6)
C19	0.7763 (8)	0.55385 (14)	0.6770 (5)	0.0581 (10)
H19A	0.8949	0.5496	0.6374	0.070*
H19B	0.6698	0.5773	0.6244	0.070*
C20	0.8290 (7)	0.54825 (14)	0.8469 (5)	0.0576 (10)
C21	1.0606 (7)	0.53519 (19)	0.9420 (5)	0.0744 (14)
H21A	1.1419	0.5629	0.9856	0.089*
H21B	1.1301	0.5213	0.8755	0.089*
C22	1.0754 (8)	0.5018 (2)	1.0714 (5)	0.0780 (15)
H22A	1.0733	0.5192	1.1600	0.094*
H22B	1.2148	0.4856	1.1005	0.094*
C23	0.8863 (8)	0.46573 (17)	1.0287 (4)	0.0668 (12)
H23A	0.9128	0.4453	1.1160	0.080*
H23B	0.7505	0.4821	1.0153	0.080*
C24	0.8494 (6)	0.43614 (13)	0.8876 (4)	0.0461 (8)
C25	0.7986 (4)	0.46457 (11)	0.7330 (3)	0.0303 (6)
H25	0.9394	0.4701	0.7193	0.036*
C26	0.6606 (5)	0.43506 (11)	0.5985 (3)	0.0342 (6)
H26	0.6844	0.4020	0.6202	0.041*
C27	0.5955 (6)	0.44536 (12)	0.4307 (4)	0.0420 (7)
C28	0.4215 (5)	0.44596 (12)	0.5037 (4)	0.0397 (7)
C29	0.3360 (5)	0.49256 (14)	0.5310 (4)	0.0480 (8)
H29A	0.1789	0.4904	0.5092	0.058*
H29B	0.3598	0.5149	0.4605	0.058*
C30	0.4486 (5)	0.50968 (12)	0.6966 (4)	0.0432 (8)
H30A	0.3931	0.5400	0.7077	0.052*
H30B	0.4147	0.4889	0.7672	0.052*
C31	0.7208 (9)	0.58031 (16)	0.9285 (6)	0.0798 (15)
H31A	0.7704	0.5728	1.0359	0.120*
H31B	0.5641	0.5768	0.8851	0.120*
H31C	0.7594	0.6116	0.9160	0.120*
C32	1.0426 (8)	0.40470 (18)	0.9033 (5)	0.0735 (14)
H32A	1.0118	0.3867	0.8113	0.110*
H32B	1.0663	0.3845	0.9895	0.110*
H32C	1.1719	0.4230	0.9189	0.110*
C33	0.6514 (8)	0.40410 (17)	0.8819 (5)	0.0726 (13)
H33A	0.6175	0.3839	0.7947	0.109*
H33B	0.5253	0.4227	0.8731	0.109*
H33C	0.6905	0.3861	0.9743	0.109*
C34	0.2538 (7)	0.40760 (16)	0.4689 (5)	0.0673 (12)
H34A	0.1552	0.4129	0.5238	0.101*
H34B	0.3275	0.3787	0.5003	0.101*
H34C	0.1721	0.4069	0.3605	0.101*
Cl1	0.47292 (16)	0.69665 (3)	0.91612 (10)	0.0568 (3)
Cl2	0.49526 (19)	0.79455 (4)	0.96635 (12)	0.0720 (3)
Cl3	0.67805 (15)	0.49544 (3)	0.36075 (10)	0.0534 (2)
Cl4	0.59779 (19)	0.39852 (4)	0.30805 (12)	0.0682 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0416 (15)	0.0354 (16)	0.0306 (14)	−0.0034 (12)	0.0097 (13)	0.0025 (12)
C2	0.070 (2)	0.0372 (18)	0.0417 (18)	0.0024 (17)	0.0129 (17)	0.0019 (16)
C3	0.073 (2)	0.0385 (19)	0.0401 (17)	−0.0065 (16)	0.0186 (17)	−0.0079 (15)
C4	0.078 (3)	0.071 (3)	0.059 (3)	−0.002 (2)	0.030 (2)	−0.024 (2)
C5	0.095 (3)	0.096 (4)	0.043 (2)	−0.028 (3)	0.037 (2)	−0.016 (2)
C6	0.071 (2)	0.079 (3)	0.0291 (17)	−0.020 (2)	0.0051 (17)	0.0116 (19)
C7	0.0495 (18)	0.046 (2)	0.0351 (16)	−0.0086 (14)	0.0098 (14)	0.0099 (15)
C8	0.0271 (12)	0.0390 (17)	0.0299 (14)	−0.0022 (11)	0.0068 (11)	0.0042 (13)
C9	0.0392 (15)	0.0334 (17)	0.0387 (16)	0.0045 (12)	0.0110 (13)	0.0014 (13)
C10	0.0448 (16)	0.0470 (19)	0.0360 (17)	0.0013 (15)	0.0071 (14)	−0.0069 (15)
C11	0.0448 (17)	0.055 (2)	0.0373 (17)	0.0108 (15)	0.0153 (14)	−0.0027 (16)
C12	0.0442 (18)	0.069 (3)	0.0476 (19)	−0.0008 (16)	0.0243 (16)	0.0038 (18)
C13	0.0411 (16)	0.052 (2)	0.0459 (18)	−0.0127 (15)	0.0085 (14)	0.0053 (16)
C14	0.113 (4)	0.059 (3)	0.055 (2)	−0.033 (3)	0.016 (3)	−0.011 (2)
C15	0.074 (3)	0.070 (3)	0.066 (3)	−0.020 (2)	0.033 (2)	0.015 (2)
C16	0.060 (2)	0.064 (3)	0.066 (3)	0.011 (2)	0.008 (2)	0.026 (2)
C17	0.071 (3)	0.082 (3)	0.070 (3)	0.030 (2)	0.031 (2)	−0.008 (3)
C18	0.0427 (15)	0.0332 (15)	0.0276 (13)	0.0043 (12)	0.0127 (12)	0.0020 (12)
C19	0.085 (3)	0.043 (2)	0.047 (2)	−0.0151 (19)	0.023 (2)	0.0003 (17)
C20	0.075 (3)	0.047 (2)	0.0443 (19)	−0.0106 (18)	0.0136 (19)	−0.0099 (17)
C21	0.058 (2)	0.098 (4)	0.059 (3)	−0.032 (2)	0.011 (2)	−0.033 (3)
C22	0.071 (3)	0.106 (4)	0.043 (2)	0.018 (3)	0.002 (2)	−0.018 (3)
C23	0.087 (3)	0.081 (3)	0.0308 (17)	0.030 (2)	0.0176 (19)	0.0110 (19)
C24	0.0533 (19)	0.048 (2)	0.0360 (17)	0.0193 (16)	0.0143 (15)	0.0081 (15)
C25	0.0284 (13)	0.0369 (16)	0.0276 (13)	0.0041 (11)	0.0123 (11)	0.0012 (12)
C26	0.0371 (15)	0.0317 (16)	0.0357 (16)	0.0029 (12)	0.0151 (13)	−0.0006 (13)
C27	0.0438 (17)	0.0473 (19)	0.0337 (16)	−0.0016 (13)	0.0121 (14)	−0.0058 (14)
C28	0.0363 (15)	0.0465 (19)	0.0356 (17)	−0.0070 (13)	0.0116 (14)	−0.0016 (14)
C29	0.0315 (14)	0.062 (2)	0.0490 (18)	0.0073 (15)	0.0125 (14)	−0.0024 (18)
C30	0.0402 (16)	0.0425 (18)	0.0471 (18)	0.0129 (14)	0.0154 (14)	−0.0002 (15)
C31	0.113 (4)	0.060 (3)	0.059 (3)	0.011 (3)	0.020 (3)	−0.026 (2)
C32	0.083 (3)	0.077 (3)	0.061 (2)	0.042 (3)	0.026 (2)	0.024 (2)
C33	0.099 (3)	0.066 (3)	0.062 (3)	−0.003 (2)	0.040 (3)	0.023 (2)
C34	0.052 (2)	0.076 (3)	0.062 (2)	−0.029 (2)	0.0056 (19)	−0.003 (2)
Cl1	0.0599 (5)	0.0659 (6)	0.0385 (4)	0.0183 (4)	0.0095 (4)	0.0086 (4)
Cl2	0.0732 (6)	0.0774 (7)	0.0529 (6)	−0.0071 (6)	0.0064 (5)	−0.0284 (5)
Cl3	0.0543 (5)	0.0693 (6)	0.0364 (4)	−0.0085 (4)	0.0157 (4)	0.0074 (4)
Cl4	0.0801 (7)	0.0748 (7)	0.0458 (5)	0.0036 (5)	0.0170 (5)	−0.0248 (5)

Geometric parameters (Å, º) top

C1—C3	1.515 (5)	C18—C30	1.504 (4)
C1—C2	1.521 (5)	C18—C19	1.505 (5)
C1—C13	1.522 (5)	C18—C20	1.520 (5)
C1—C8	1.530 (4)	C18—C25	1.539 (4)
C2—C3	1.518 (5)	C19—C20	1.502 (6)
C2—H2A	0.9700	C19—H19A	0.9700
C2—H2B	0.9700	C19—H19B	0.9700
C3—C4	1.512 (6)	C20—C21	1.502 (6)
C3—C14	1.520 (6)	C20—C31	1.518 (6)
C4—C5	1.512 (7)	C21—C22	1.520 (7)
C4—H4A	0.9700	C21—H21A	0.9700
C4—H4B	0.9700	C21—H21B	0.9700
C5—C6	1.554 (7)	C22—C23	1.556 (8)
C5—H5A	0.9700	C22—H22A	0.9700
C5—H5B	0.9700	C22—H22B	0.9700
C6—C7	1.539 (5)	C23—C24	1.513 (6)
C6—H6A	0.9700	C23—H23A	0.9700
C6—H6B	0.9700	C23—H23B	0.9700
C7—C15	1.524 (5)	C24—C32	1.516 (5)
C7—C16	1.561 (6)	C24—C33	1.572 (6)
C7—C8	1.583 (4)	C24—C25	1.587 (4)
C8—C9	1.519 (4)	C25—C26	1.521 (4)
C8—H8	0.9800	C25—H25	0.9800
C9—C10	1.491 (5)	C26—C27	1.495 (5)
C9—C11	1.530 (5)	C26—C28	1.527 (4)
C9—H9	0.9800	C26—H26	0.9800
C10—C11	1.498 (4)	C27—C28	1.507 (5)
C10—Cl1	1.760 (4)	C27—Cl3	1.750 (4)
C10—Cl2	1.769 (3)	C27—Cl4	1.776 (4)
C11—C12	1.519 (5)	C28—C34	1.511 (5)
C11—C17	1.521 (5)	C28—C29	1.515 (5)
C12—C13	1.530 (5)	C29—C30	1.536 (5)
C12—H12A	0.9700	C29—H29A	0.9700
C12—H12B	0.9700	C29—H29B	0.9700
C13—H13A	0.9700	C30—H30A	0.9700
C13—H13B	0.9700	C30—H30B	0.9700
C14—H14A	0.9600	C31—H31A	0.9600
C14—H14B	0.9600	C31—H31B	0.9600
C14—H14C	0.9600	C31—H31C	0.9600
C15—H15A	0.9600	C32—H32A	0.9600
C15—H15B	0.9600	C32—H32B	0.9600
C15—H15C	0.9600	C32—H32C	0.9600
C16—H16A	0.9600	C33—H33A	0.9600
C16—H16B	0.9600	C33—H33B	0.9600
C16—H16C	0.9600	C33—H33C	0.9600
C17—H17A	0.9600	C34—H34A	0.9600
C17—H17B	0.9600	C34—H34B	0.9600
C17—H17C	0.9600	C34—H34C	0.9600

C3—C1—C2	60.0 (2)	C30—C18—C19	115.4 (3)
C3—C1—C13	120.9 (3)	C30—C18—C20	120.4 (3)
C2—C1—C13	115.5 (3)	C19—C18—C20	59.5 (2)
C3—C1—C8	118.8 (3)	C30—C18—C25	113.2 (3)
C2—C1—C8	119.2 (3)	C19—C18—C25	119.9 (3)
C13—C1—C8	112.7 (3)	C20—C18—C25	118.4 (3)
C3—C2—C1	59.8 (2)	C20—C19—C18	60.7 (2)
C3—C2—H2A	117.8	C20—C19—H19A	117.7
C1—C2—H2A	117.8	C18—C19—H19A	117.7
C3—C2—H2B	117.8	C20—C19—H19B	117.7
C1—C2—H2B	117.8	C18—C19—H19B	117.7
H2A—C2—H2B	114.9	H19A—C19—H19B	114.8
C4—C3—C1	116.1 (3)	C21—C20—C19	117.3 (4)
C4—C3—C2	116.4 (4)	C21—C20—C31	113.9 (4)
C1—C3—C2	60.2 (2)	C19—C20—C31	118.9 (4)
C4—C3—C14	113.7 (4)	C21—C20—C18	116.6 (3)
C1—C3—C14	120.9 (4)	C19—C20—C18	59.8 (2)
C2—C3—C14	119.5 (4)	C31—C20—C18	120.3 (4)
C5—C4—C3	112.9 (4)	C20—C21—C22	113.5 (4)
C5—C4—H4A	109.0	C20—C21—H21A	108.9
C3—C4—H4A	109.0	C22—C21—H21A	108.9
C5—C4—H4B	109.0	C20—C21—H21B	108.9
C3—C4—H4B	109.0	C22—C21—H21B	108.9
H4A—C4—H4B	107.8	H21A—C21—H21B	107.7
C4—C5—C6	113.6 (3)	C21—C22—C23	113.6 (3)
C4—C5—H5A	108.8	C21—C22—H22A	108.8
C6—C5—H5A	108.8	C23—C22—H22A	108.8
C4—C5—H5B	108.8	C21—C22—H22B	108.8
C6—C5—H5B	108.8	C23—C22—H22B	108.8
H5A—C5—H5B	107.7	H22A—C22—H22B	107.7
C7—C6—C5	117.7 (4)	C24—C23—C22	118.3 (4)
C7—C6—H6A	107.9	C24—C23—H23A	107.7
C5—C6—H6A	107.9	C22—C23—H23A	107.7
C7—C6—H6B	107.9	C24—C23—H23B	107.7
C5—C6—H6B	107.9	C22—C23—H23B	107.7
H6A—C6—H6B	107.2	H23A—C23—H23B	107.1
C15—C7—C6	111.4 (3)	C23—C24—C32	112.5 (3)
C15—C7—C16	107.2 (3)	C23—C24—C33	104.2 (4)
C6—C7—C16	103.9 (3)	C32—C24—C33	106.7 (4)
C15—C7—C8	108.5 (3)	C23—C24—C25	114.1 (3)
C6—C7—C8	113.0 (3)	C32—C24—C25	107.6 (3)
C16—C7—C8	112.7 (3)	C33—C24—C25	111.5 (3)
C9—C8—C1	113.0 (3)	C26—C25—C18	112.3 (2)
C9—C8—C7	108.9 (3)	C26—C25—C24	109.1 (3)
C1—C8—C7	114.2 (2)	C18—C25—C24	113.7 (2)
C9—C8—H8	106.8	C26—C25—H25	107.1
C1—C8—H8	106.8	C18—C25—H25	107.1
C7—C8—H8	106.8	C24—C25—H25	107.1
C10—C9—C8	128.5 (3)	C27—C26—C25	127.9 (3)
C10—C9—C11	59.5 (2)	C27—C26—C28	59.8 (2)
C8—C9—C11	122.9 (3)	C25—C26—C28	123.1 (3)
C10—C9—H9	112.0	C27—C26—H26	112.1
C8—C9—H9	112.0	C25—C26—H26	112.1
C11—C9—H9	112.0	C28—C26—H26	112.1
C9—C10—C11	61.6 (2)	C26—C27—C28	61.1 (2)
C9—C10—Cl1	122.1 (3)	C26—C27—Cl3	122.7 (2)
C11—C10—Cl1	121.8 (3)	C28—C27—Cl3	122.2 (3)
C9—C10—Cl2	117.0 (3)	C26—C27—Cl4	116.9 (3)
C11—C10—Cl2	118.9 (3)	C28—C27—Cl4	118.2 (2)
Cl1—C10—Cl2	108.94 (17)	Cl3—C27—Cl4	108.95 (19)
C10—C11—C12	118.1 (3)	C27—C28—C34	119.5 (3)
C10—C11—C17	118.8 (3)	C27—C28—C29	117.5 (3)
C12—C11—C17	114.7 (3)	C34—C28—C29	114.4 (3)
C10—C11—C9	59.0 (2)	C27—C28—C26	59.1 (2)
C12—C11—C9	116.3 (3)	C34—C28—C26	118.9 (3)
C17—C11—C9	118.9 (4)	C29—C28—C26	116.5 (3)
C11—C12—C13	112.7 (3)	C28—C29—C30	112.4 (3)
C11—C12—H12A	109.0	C28—C29—H29A	109.1
C13—C12—H12A	109.0	C30—C29—H29A	109.1
C11—C12—H12B	109.0	C28—C29—H29B	109.1
C13—C12—H12B	109.0	C30—C29—H29B	109.1
H12A—C12—H12B	107.8	H29A—C29—H29B	107.9
C1—C13—C12	110.6 (3)	C18—C30—C29	110.5 (3)
C1—C13—H13A	109.5	C18—C30—H30A	109.6
C12—C13—H13A	109.5	C29—C30—H30A	109.6
C1—C13—H13B	109.5	C18—C30—H30B	109.6
C12—C13—H13B	109.5	C29—C30—H30B	109.6
H13A—C13—H13B	108.1	H30A—C30—H30B	108.1
C3—C14—H14A	109.5	C20—C31—H31A	109.5
C3—C14—H14B	109.5	C20—C31—H31B	109.5
H14A—C14—H14B	109.5	H31A—C31—H31B	109.5
C3—C14—H14C	109.5	C20—C31—H31C	109.5
H14A—C14—H14C	109.5	H31A—C31—H31C	109.5
H14B—C14—H14C	109.5	H31B—C31—H31C	109.5
C7—C15—H15A	109.5	C24—C32—H32A	109.5
C7—C15—H15B	109.5	C24—C32—H32B	109.5
H15A—C15—H15B	109.5	H32A—C32—H32B	109.5
C7—C15—H15C	109.5	C24—C32—H32C	109.5
H15A—C15—H15C	109.5	H32A—C32—H32C	109.5
H15B—C15—H15C	109.5	H32B—C32—H32C	109.5
C7—C16—H16A	109.5	C24—C33—H33A	109.5
C7—C16—H16B	109.5	C24—C33—H33B	109.5
H16A—C16—H16B	109.5	H33A—C33—H33B	109.5
C7—C16—H16C	109.5	C24—C33—H33C	109.5
H16A—C16—H16C	109.5	H33A—C33—H33C	109.5
H16B—C16—H16C	109.5	H33B—C33—H33C	109.5
C11—C17—H17A	109.5	C28—C34—H34A	109.5
C11—C17—H17B	109.5	C28—C34—H34B	109.5
H17A—C17—H17B	109.5	H34A—C34—H34B	109.5
C11—C17—H17C	109.5	C28—C34—H34C	109.5
H17A—C17—H17C	109.5	H34A—C34—H34C	109.5
H17B—C17—H17C	109.5	H34B—C34—H34C	109.5

Experimental details

Crystal data
Chemical formula	C₁₇H₂₆Cl₂
M_r	301.28
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	6.4930 (2), 29.0000 (8), 9.2854 (4)
β (°)	110.454 (1)
V (Å³)	1638.18 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.45 × 0.35 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10017, 5832, 5438
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.123, 1.09
No. of reflections	5832
No. of parameters	343
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.21
Absolute structure	Flack & Bernardinelli (2000), 1283 Friedel pairs
Absolute structure parameter	0.05 (6)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

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(1S,3S,8R,9S,11R)-10,10-Di­chloro-3,7,7,11-tetra­methyl­tetra­cyclo[6.5.0.01,3.09,11]trideca­ne

Supporting information

Key indicators

checkCIF/PLATON results

(1S,3S,8R,9S,11R)-10,10-Dichloro-3,7,7,11-tetramethyltetracyclo[6.5.0.0^1,3.0^9,11]tridecane