(1S,3R,8R,9S,11R)-2,2,10,10-Tetra-chloro-3,7,7,11-tetra-methyl-tetra-cyclo-[6.5.0.0(1,3).0(9,11)]trideca-ne.

The title compound, C(17)H(24)Cl(4), was synthesized from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule is built up from fused six- and seven-membered rings and two three-membered rings from the reaction of β-himachalene with dichloro-carbene. The six-membered ring shows a chair conformation, whereas the seven-membered ring displays a boat conformation.

Related literature

For the isolation of β-himachalene, see: Joseph & Dev (1968 ▶); Plattier & Teisseire (1974 ▶). For the reactivity of this sesquiterpene, see: Lassaba et al. (1998 ▶); Chekroun et al. (2000 ▶); El Jamili et al. (2002 ▶); Sbai et al. (2002 ▶); Dakir et al. (2004 ▶). For its biological activity, see: Daoubi et al. (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H24Cl4

M = 370.16

Monoclinic,

a = 8.8807 (6) Å

b = 11.6280 (8) Å

c = 9.0596 (6) Å

β = 107.665 (2)°

V = 891.42 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.66 mm−1

T = 296 K

0.41 × 0.35 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer

15112 measured reflections

5419 independent reflections

4910 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.03

5419 reflections

190 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶)

Flack parameter: 0.04 (4)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001700/bt6883sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001700/bt6883Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001700/bt6883Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H24Cl4	F(000) = 388
Mr = 370.16	Dx = 1.379 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5419 reflections
a = 8.8807 (6) Å	θ = 2.8–30.5°
b = 11.6280 (8) Å	µ = 0.66 mm−1
c = 9.0596 (6) Å	T = 296 K
β = 107.665 (2)°	Block, colourless
V = 891.42 (10) Å3	0.41 × 0.35 × 0.27 mm
Z = 2

Bruker X8 APEX diffractometer	4910 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 30.5°, θmin = 2.8°
φ and ω scans	h = −12→12
15112 measured reflections	k = −16→16
5419 independent reflections	l = −12→12

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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.074P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
5419 reflections	Δρmax = 0.32 e Å−3
190 parameters	Δρmin = −0.19 e Å−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (4)

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.

	x	y	z	Uiso*/Ueq
Cl1	0.38317 (6)	0.32772 (6)	0.92294 (6)	0.06701 (17)
Cl2	0.52164 (6)	0.12723 (5)	0.83384 (6)	0.05443 (13)
Cl3	0.78628 (6)	0.23092 (5)	1.13768 (5)	0.05374 (13)
Cl4	1.12169 (5)	0.25246 (4)	1.19453 (5)	0.04960 (12)
C1	0.62379 (15)	0.35612 (13)	0.77816 (16)	0.0288 (3)
C2	0.49711 (18)	0.27743 (16)	0.80650 (18)	0.0391 (4)
C3	0.47133 (16)	0.32604 (17)	0.64690 (18)	0.0380 (3)
C4	0.48758 (19)	0.24243 (18)	0.52377 (18)	0.0431 (4)
H4A	0.5552	0.1791	0.5733	0.052*
H4B	0.3845	0.2111	0.4692	0.052*
C5	0.5566 (2)	0.2997 (2)	0.40815 (19)	0.0518 (5)
H5A	0.4729	0.3396	0.3311	0.062*
H5B	0.5980	0.2408	0.3552	0.062*
C6	0.6879 (2)	0.38477 (18)	0.48244 (18)	0.0442 (4)
H6A	0.6393	0.4506	0.5156	0.053*
H6B	0.7306	0.4116	0.4019	0.053*
C7	0.82871 (16)	0.34716 (14)	0.62113 (16)	0.0324 (3)
C8	0.77955 (14)	0.30517 (11)	0.76794 (14)	0.0244 (2)
H8	0.7717	0.2249	0.7579	0.029*
C9	0.91820 (15)	0.32805 (12)	0.91322 (15)	0.0269 (2)
H9	1.0184	0.3143	0.8884	0.032*
C10	0.93290 (17)	0.29978 (13)	1.07857 (15)	0.0317 (3)
C11	0.91735 (18)	0.42382 (14)	1.02843 (17)	0.0350 (3)
C12	0.7581 (2)	0.48145 (17)	1.0110 (2)	0.0474 (4)
H12A	0.7766	0.5613	1.0420	0.057*
H12B	0.7095	0.4446	1.0812	0.057*
C13	0.64262 (19)	0.47670 (14)	0.84681 (19)	0.0377 (3)
H13A	0.5402	0.5044	0.8488	0.045*
H13B	0.6798	0.5277	0.7806	0.045*
C14	0.3446 (2)	0.4161 (2)	0.5839 (2)	0.0545 (5)
H14A	0.3648	0.4816	0.6516	0.082*
H14B	0.2430	0.3844	0.5775	0.082*
H14C	0.3457	0.4395	0.4826	0.082*
C15	0.9169 (2)	0.2471 (2)	0.57360 (19)	0.0469 (4)
H15A	0.8513	0.1798	0.5550	0.070*
H15B	1.0128	0.2318	0.6552	0.070*
H15C	0.9418	0.2672	0.4809	0.070*
C16	0.9411 (2)	0.45147 (18)	0.6573 (2)	0.0459 (4)
H16A	1.0290	0.4353	0.7471	0.069*
H16B	0.8854	0.5177	0.6767	0.069*
H16C	0.9789	0.4664	0.5704	0.069*
C17	1.0594 (2)	0.50220 (16)	1.0855 (2)	0.0529 (5)
H17A	1.0320	0.5781	1.0443	0.079*
H17B	1.1446	0.4729	1.0518	0.079*
H17C	1.0917	0.5053	1.1967	0.079*

	U11	U22	U33	U12	U13	U23
Cl1	0.0372 (2)	0.1166 (5)	0.0572 (3)	0.0018 (3)	0.0294 (2)	−0.0039 (3)
Cl2	0.0510 (2)	0.0575 (3)	0.0527 (3)	−0.0213 (2)	0.0126 (2)	0.0075 (2)
Cl3	0.0529 (2)	0.0783 (3)	0.03199 (18)	−0.0149 (2)	0.01578 (16)	0.00474 (19)
Cl4	0.0432 (2)	0.0512 (2)	0.03845 (19)	0.00492 (18)	−0.01151 (15)	0.00149 (18)
C1	0.0203 (5)	0.0383 (7)	0.0276 (6)	0.0004 (5)	0.0068 (5)	−0.0003 (5)
C2	0.0253 (6)	0.0579 (10)	0.0358 (7)	−0.0060 (6)	0.0120 (5)	−0.0007 (7)
C3	0.0202 (6)	0.0576 (10)	0.0339 (7)	−0.0013 (6)	0.0046 (5)	0.0000 (7)
C4	0.0305 (7)	0.0607 (10)	0.0318 (7)	−0.0065 (7)	−0.0001 (5)	−0.0055 (7)
C5	0.0408 (8)	0.0849 (15)	0.0247 (7)	−0.0039 (9)	0.0024 (6)	−0.0019 (8)
C6	0.0364 (8)	0.0666 (12)	0.0288 (7)	0.0003 (7)	0.0089 (6)	0.0111 (7)
C7	0.0268 (6)	0.0455 (8)	0.0260 (6)	−0.0005 (6)	0.0095 (5)	0.0001 (6)
C8	0.0209 (5)	0.0299 (6)	0.0212 (5)	0.0004 (5)	0.0049 (4)	−0.0022 (5)
C9	0.0220 (5)	0.0327 (6)	0.0244 (6)	0.0006 (5)	0.0048 (4)	−0.0024 (5)
C10	0.0295 (6)	0.0385 (7)	0.0234 (6)	0.0007 (6)	0.0023 (5)	−0.0018 (5)
C11	0.0321 (7)	0.0350 (7)	0.0317 (7)	0.0009 (6)	0.0006 (5)	−0.0070 (6)
C12	0.0456 (9)	0.0486 (9)	0.0434 (9)	0.0131 (7)	0.0066 (7)	−0.0172 (7)
C13	0.0319 (7)	0.0384 (8)	0.0412 (8)	0.0100 (6)	0.0087 (6)	−0.0023 (6)
C14	0.0264 (7)	0.0793 (14)	0.0513 (10)	0.0126 (8)	0.0020 (7)	0.0039 (10)
C15	0.0433 (8)	0.0676 (11)	0.0341 (7)	0.0100 (8)	0.0184 (6)	−0.0059 (8)
C16	0.0372 (8)	0.0578 (11)	0.0453 (9)	−0.0095 (7)	0.0162 (7)	0.0063 (8)
C17	0.0513 (10)	0.0410 (9)	0.0527 (10)	−0.0117 (8)	−0.0050 (8)	−0.0085 (8)

Cl1—C2	1.7682 (17)	C8—H8	0.9380
Cl2—C2	1.768 (2)	C9—C10	1.5001 (19)
Cl3—C10	1.7454 (16)	C9—C11	1.528 (2)
Cl4—C10	1.7744 (14)	C9—H9	0.9951
C1—C13	1.522 (2)	C10—C11	1.506 (2)
C1—C2	1.531 (2)	C11—C17	1.515 (2)
C1—C8	1.5332 (17)	C11—C12	1.529 (2)
C1—C3	1.5468 (19)	C12—C13	1.530 (2)
C2—C3	1.504 (2)	C12—H12A	0.9700
C3—C14	1.517 (2)	C12—H12B	0.9700
C3—C4	1.519 (2)	C13—H13A	0.9700
C4—C5	1.519 (3)	C13—H13B	0.9700
C4—H4A	0.9700	C14—H14A	0.9600
C4—H4B	0.9700	C14—H14B	0.9600
C5—C6	1.521 (3)	C14—H14C	0.9600
C5—H5A	0.9700	C15—H15A	0.9600
C5—H5B	0.9700	C15—H15B	0.9600
C6—C7	1.543 (2)	C15—H15C	0.9600
C6—H6A	0.9700	C16—H16A	0.9600
C6—H6B	0.9700	C16—H16B	0.9600
C7—C15	1.536 (2)	C16—H16C	0.9600
C7—C16	1.541 (2)	C17—H17A	0.9600
C7—C8	1.5970 (19)	C17—H17B	0.9600
C8—C9	1.5283 (17)	C17—H17C	0.9600
C13—C1—C2	118.50 (12)	C10—C9—H9	112.2
C13—C1—C8	113.04 (11)	C11—C9—H9	117.5
C2—C1—C8	120.10 (13)	C8—C9—H9	108.6
C13—C1—C3	118.97 (13)	C9—C10—C11	61.10 (10)
C2—C1—C3	58.50 (10)	C9—C10—Cl3	124.05 (10)
C8—C1—C3	117.48 (12)	C11—C10—Cl3	121.55 (11)
C3—C2—C1	61.28 (10)	C9—C10—Cl4	116.07 (10)
C3—C2—Cl2	118.84 (13)	C11—C10—Cl4	117.34 (11)
C1—C2—Cl2	123.25 (12)	Cl3—C10—Cl4	109.57 (8)
C3—C2—Cl1	120.10 (13)	C10—C11—C17	118.86 (14)
C1—C2—Cl1	119.01 (12)	C10—C11—C9	59.27 (9)
Cl2—C2—Cl1	108.16 (9)	C17—C11—C9	119.72 (15)
C2—C3—C14	120.05 (14)	C10—C11—C12	116.63 (15)
C2—C3—C4	116.41 (16)	C17—C11—C12	114.83 (15)
C14—C3—C4	112.99 (14)	C9—C11—C12	116.42 (12)
C2—C3—C1	60.23 (9)	C11—C12—C13	114.26 (13)
C14—C3—C1	120.64 (16)	C11—C12—H12A	108.7
C4—C3—C1	116.95 (12)	C13—C12—H12A	108.7
C5—C4—C3	111.97 (17)	C11—C12—H12B	108.7
C5—C4—H4A	109.2	C13—C12—H12B	108.7
C3—C4—H4A	109.2	H12A—C12—H12B	107.6
C5—C4—H4B	109.2	C1—C13—C12	112.86 (13)
C3—C4—H4B	109.2	C1—C13—H13A	109.0
H4A—C4—H4B	107.9	C12—C13—H13A	109.0
C4—C5—C6	113.30 (13)	C1—C13—H13B	109.0
C4—C5—H5A	108.9	C12—C13—H13B	109.0
C6—C5—H5A	108.9	H13A—C13—H13B	107.8
C4—C5—H5B	108.9	C3—C14—H14A	109.5
C6—C5—H5B	108.9	C3—C14—H14B	109.5
H5A—C5—H5B	107.7	H14A—C14—H14B	109.5
C5—C6—C7	119.92 (16)	C3—C14—H14C	109.5
C5—C6—H6A	107.3	H14A—C14—H14C	109.5
C7—C6—H6A	107.3	H14B—C14—H14C	109.5
C5—C6—H6B	107.3	C7—C15—H15A	109.5
C7—C6—H6B	107.3	C7—C15—H15B	109.5
H6A—C6—H6B	106.9	H15A—C15—H15B	109.5
C15—C7—C16	107.65 (13)	C7—C15—H15C	109.5
C15—C7—C6	110.06 (13)	H15A—C15—H15C	109.5
C16—C7—C6	105.23 (14)	H15B—C15—H15C	109.5
C15—C7—C8	107.07 (13)	C7—C16—H16A	109.5
C16—C7—C8	112.76 (12)	C7—C16—H16B	109.5
C6—C7—C8	113.95 (11)	H16A—C16—H16B	109.5
C9—C8—C1	112.74 (10)	C7—C16—H16C	109.5
C9—C8—C7	108.15 (10)	H16A—C16—H16C	109.5
C1—C8—C7	114.32 (11)	H16B—C16—H16C	109.5
C9—C8—H8	105.9	C11—C17—H17A	109.5
C1—C8—H8	110.4	C11—C17—H17B	109.5
C7—C8—H8	104.7	H17A—C17—H17B	109.5
C10—C9—C11	59.64 (10)	C11—C17—H17C	109.5
C10—C9—C8	128.69 (12)	H17A—C17—H17C	109.5
C11—C9—C8	123.06 (11)	H17B—C17—H17C	109.5