(1S,3R,8R,11S)-2,2-Dichloro-3,7,7,10-tetra­methyl­tricyclo­[6.4.0.01,3]dodec-9-en-11-ol

Benharref, A.; Lassaba, E.; Avignant, D.; Oudahmane, A.; Berraho, M.

doi:10.1107/S1600536811004788

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o615

doi:10.1107/S1600536811004788

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(1S,3R,8R,11S)-2,2-Dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-9-en-11-ol

Ahmed Benharref,^a Essêdiya Lassaba,^a ^* Daniel Avignant,^b Abdelghani Oudahmane ^b and Moha Berraho ^a

^aLaboratoire de Chimie Biomoléculaires, Substances Naturelles et Réactivité, URAC16, Faculté des Sciences, Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, and ^bUniversité Blaise Pascal, Laboratoire des Matériaux Inorganiques, UMR CNRS 6002, 24 Avenue des Landais, 63177 Aubière, France
^*Correspondence e-mail: elassaba@gmail.com

(Received 30 January 2011; accepted 8 February 2011; online 12 February 2011)

The title compound, C₁₆H₂₄Cl₂O, was synthesized from β-himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), which was isolated from essential oil of the Atlas cedar (Cedrus atlantica). The two fused rings exhibit different conformations: the six-membered ring has a screw-boat conformation, while the seven-membered ring displays a boat conformation. The dihedral angle between the two rings is 56.56 (18)°. In the crystal, molecules aggregate into supramolecular chains along the c axis mediated by O—H⋯O hydrogen bonds.

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 conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₆H₂₄Cl₂O
M_r = 303.25
Trigonal, P 3₂
a = 13.2323 (13) Å
c = 7.9807 (8) Å
V = 1210.2 (2) Å³
Z = 3
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 298 K
0.41 × 0.33 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer
8123 measured reflections
3135 independent reflections
2995 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.126
S = 1.09
3135 reflections
180 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.33 e Å⁻³
Absolute structure: Flack (1983 ), 1940 Friedel pairs
Flack parameter: −0.11 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1ⁱ	0.82	2.10	2.853 (4)	153
Symmetry code: (i) $[-y+2, x-y, z-{\script{1\over 3}}]$ .

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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004788/tk2714sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004788/tk2714Isup2.hkl

checkCIF report

Comment top

The bicyclic sesquiterpene β-himachalene is the main constituent of the essential oil of the Atlas cedar (Cedrus atlantica) (Joseph & Dev, 1968; Plattier & Teisseire, 1974). The reactivity of this sesquiterpene and its derivatives has been studied extensively by our team in order to prepare new products having biological proprieties (Lassaba et al., 1998; Chekroun et al., 2000; El Jamili et al., 2002; Sbai et al., 2002; Dakir et al., 2004). Indeed, these compounds were tested, using the food poisoning technique, for their potential antifungal activity against the phytopathogen Botrytis cinerea (Daoubi et al., 2004).

The action of one equivalent of dichlorocarbene, generated in situ from chloroform in the presence of sodium hydroxide as base and n-benzyltriethylammonium chloride as catalyst, on β-himachalene produces only (1S,3R,8R)-2,2-dichloro-3,7,7,10- tetramethyltricyclo[6.4.0.0^1,3]dodec-9-ene (El Jamili et al., 2002). Treatment of the latter compound with two equivalents of N-bromosuccinimide gives (1S, 3R, 8R, 11S)-2,2-dichloro -3,7,7,10-tetralethyltricyclo[6.4.0.0^1,3]dodec-9-en-11-ol in a very low yield (5%), along with other products. The structure of this new product was determined by NMR (¹H & ¹³C) spectral analysis and mass spectroscopy, and confirmed by a crystallographic study, reported herein.

The molecule is built up from two fused six-membered and seven-membered rings (Fig. 1). The six-membered ring has a screw boat conformation, as indicated by the total puckering amplitude QT = 0.480 (3) Å and spherical polar angle θ = 130.6 (4) ° with ϕ = 151.5 (5) °, whereas the seven-membered ring displays a boat conformation with QT = 1.1449 (30) Å, θ₂ = 88.29 (15) °, ϕ₂ = -47.13 (14) ° and ϕ₃ =-144.24 (5) ° (Cremer & Pople, 1975). In the crystal structure, molecules are linked into supramolecular chains (Fig. 2) running along the c axis by O—H···O hydrogen bonds (Table 1). Owing to the presence of Cl atoms, the absolute configuration could be fully confirmed, as C1(S), C3(R), C8(R) and C11(S).

Related literature top

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 conformational analysis, see: Cremer & Pople (1975).

Experimental top

In a reactor containing a solution of (1S, 3R, 8R)-2,2-dichloro-3,7,7,10 tetramethyltricyclo [6.4.0.0^1,3] dodec-9-ene (1 g, 3.48 mmol) in 50 ml of tetrahydrofuran and water (THF/H₂O) (4:1) cooled to 273 K and kept in the dark, was added in small portions 1.23 g (6.96 mmol) of N-bromosccinimide. The reaction mixture was left stirring for 1 h, after which 20 ml of a saturated solution of NaHCO₃ was added. Subsequently, the extraction was performed three times with diethyl ether (3 x 20 ml). The organic extracts were dried over Na₂SO₄, filtered, concentrated, and chromatographed. The title compound, (1S, 3R, 8R, 11S,)-2,2-dichloro-3,7,7,10-tetralethyltricyclo [6.4.0.0^1,3] dodec-9-by-11-ol was obtained with in a yield of 5% and was recrystallized its pentane solution.

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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing diagram showing the O—H···O interactions (dashed lines) and the formation of supramolecular chains parallel to the c axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

(1S,3R,8R,11S)-2,2-Dichloro-3,7,7,10- tetramethyltricyclo[6.4.0.0^1,3]dodec-9-en-11-ol top

Crystal data top

C₁₆H₂₄Cl₂O	D_x = 1.244 Mg m⁻³
M_r = 303.25	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3₂	Cell parameters from 8123 reflections
Hall symbol: P 32	θ = 4–26.4°
a = 13.2323 (13) Å	µ = 0.39 mm⁻¹
c = 7.9807 (8) Å	T = 298 K
V = 1210.2 (2) Å³	Prism, colourless
Z = 3	0.41 × 0.33 × 0.26 mm
F(000) = 486

Data collection top

Bruker APEXII CCD diffractometer	2995 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Graphite monochromator	θ_max = 26.4°, θ_min = 4.0°
ω and ϕ scans	h = −15→16
8123 measured reflections	k = −14→16
3135 independent reflections	l = −9→9

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0761P)² + 0.4405P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
3135 reflections	Δρ_max = 0.52 e Å⁻³
180 parameters	Δρ_min = −0.33 e Å⁻³
1 restraint	Absolute structure: Flack & Bernardinelli (2000), 1940 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.11 (7)

Crystal data top

C₁₆H₂₄Cl₂O	Z = 3
M_r = 303.25	Mo Kα radiation
Trigonal, P3₂	µ = 0.39 mm⁻¹
a = 13.2323 (13) Å	T = 298 K
c = 7.9807 (8) Å	0.41 × 0.33 × 0.26 mm
V = 1210.2 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	2995 reflections with I > 2σ(I)
8123 measured reflections	R_int = 0.019
3135 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.126	Δρ_max = 0.52 e Å⁻³
S = 1.09	Δρ_min = −0.33 e Å⁻³
3135 reflections	Absolute structure: Flack & Bernardinelli (2000), 1940 Friedel pairs
180 parameters	Absolute structure parameter: −0.11 (7)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	1.0043 (2)	0.6432 (2)	0.5388 (3)	0.0304 (5)
C2	0.9057 (2)	0.5880 (2)	0.4113 (4)	0.0370 (5)
C3	0.8790 (2)	0.5564 (2)	0.5938 (4)	0.0392 (6)
C4	0.8143 (3)	0.6069 (3)	0.6915 (4)	0.0464 (7)
H4A	0.8228	0.6749	0.6329	0.056*
H4B	0.7319	0.5493	0.6955	0.056*
C5	0.8600 (3)	0.6411 (3)	0.8682 (5)	0.0541 (8)
H5A	0.8234	0.5720	0.9384	0.065*
H5B	0.8370	0.6953	0.9106	0.065*
C6	0.9973 (3)	0.6991 (4)	0.8854 (5)	0.0591 (9)
H6A	1.0178	0.7232	1.0010	0.071*
H6B	1.0175	0.6394	0.8633	0.071*
C7	1.0733 (2)	0.8032 (3)	0.7746 (4)	0.0426 (6)
C8	1.0545 (2)	0.7728 (2)	0.5810 (3)	0.0308 (5)
H8	0.9966	0.7933	0.5426	0.041 (8)*
C9	1.1625 (2)	0.8449 (2)	0.4781 (4)	0.0394 (6)
H9	1.1895	0.9246	0.4721	0.039 (8)*
C10	1.2228 (2)	0.8058 (2)	0.3951 (4)	0.0367 (5)
C11	1.1869 (2)	0.6778 (2)	0.3958 (3)	0.0333 (5)
H11	1.1523	0.6443	0.2867	0.029 (7)*
C12	1.0980 (2)	0.6089 (2)	0.5320 (4)	0.0364 (5)
H12A	1.0624	0.5260	0.5090	0.044*
H12B	1.1371	0.6242	0.6396	0.044*
C13	1.3285 (3)	0.8828 (3)	0.2905 (5)	0.0549 (8)
H13A	1.3407	0.9607	0.2893	0.082*
H13B	1.3164	0.8532	0.1780	0.082*
H13C	1.3957	0.8837	0.3373	0.082*
C14	0.8465 (3)	0.4338 (3)	0.6503 (6)	0.0633 (10)
H14A	0.7653	0.3913	0.6796	0.095*
H14B	0.8927	0.4386	0.7459	0.095*
H14C	0.8611	0.3943	0.5608	0.095*
C15	1.0481 (4)	0.9031 (4)	0.8042 (6)	0.0718 (11)
H15A	0.9719	0.8811	0.7621	0.108*
H15B	1.1055	0.9718	0.7469	0.108*
H15C	1.0512	0.9188	0.9221	0.108*
C16	1.2019 (4)	0.8507 (4)	0.8255 (6)	0.0730 (11)
H16A	1.2122	0.8740	0.9410	0.109*
H16B	1.2515	0.9168	0.7568	0.109*
H16C	1.2219	0.7909	0.8102	0.109*
O1	1.28683 (18)	0.6633 (2)	0.4212 (3)	0.0453 (5)
H1	1.3211	0.6727	0.3319	0.068*
Cl1	0.85533 (6)	0.67322 (7)	0.30875 (9)	0.0497 (2)
Cl2	0.90015 (7)	0.48357 (7)	0.26866 (11)	0.0605 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0314 (11)	0.0304 (11)	0.0315 (12)	0.0170 (10)	0.0015 (9)	0.0018 (9)
C2	0.0353 (12)	0.0343 (12)	0.0391 (14)	0.0157 (10)	−0.0032 (10)	−0.0049 (10)
C3	0.0350 (13)	0.0374 (13)	0.0431 (15)	0.0164 (11)	0.0042 (11)	0.0079 (11)
C4	0.0365 (14)	0.0604 (18)	0.0436 (16)	0.0253 (13)	0.0107 (11)	0.0114 (13)
C5	0.0556 (19)	0.069 (2)	0.0418 (16)	0.0344 (17)	0.0144 (14)	0.0117 (15)
C6	0.065 (2)	0.079 (2)	0.0401 (17)	0.0407 (19)	−0.0012 (14)	0.0047 (16)
C7	0.0435 (14)	0.0539 (16)	0.0364 (14)	0.0289 (13)	−0.0053 (11)	−0.0123 (12)
C8	0.0306 (11)	0.0319 (12)	0.0351 (12)	0.0197 (10)	0.0012 (9)	−0.0015 (9)
C9	0.0409 (14)	0.0287 (12)	0.0461 (16)	0.0155 (10)	0.0048 (11)	0.0006 (10)
C10	0.0320 (12)	0.0339 (13)	0.0409 (14)	0.0141 (10)	0.0025 (10)	−0.0003 (10)
C11	0.0327 (12)	0.0367 (12)	0.0365 (14)	0.0218 (10)	−0.0017 (9)	−0.0045 (10)
C12	0.0369 (12)	0.0343 (12)	0.0451 (14)	0.0230 (11)	0.0031 (10)	0.0023 (10)
C13	0.0452 (16)	0.0493 (17)	0.064 (2)	0.0190 (14)	0.0200 (15)	0.0072 (14)
C14	0.0562 (19)	0.0404 (16)	0.082 (3)	0.0158 (15)	0.0123 (17)	0.0191 (16)
C15	0.078 (3)	0.071 (2)	0.078 (3)	0.046 (2)	0.002 (2)	−0.023 (2)
C16	0.058 (2)	0.087 (3)	0.069 (3)	0.033 (2)	−0.0150 (19)	−0.023 (2)
O1	0.0410 (10)	0.0614 (13)	0.0479 (12)	0.0365 (10)	0.0009 (8)	−0.0025 (9)
Cl1	0.0471 (4)	0.0680 (5)	0.0384 (3)	0.0321 (4)	−0.0065 (3)	0.0047 (3)
Cl2	0.0541 (4)	0.0536 (4)	0.0643 (5)	0.0199 (4)	−0.0071 (4)	−0.0266 (4)

Geometric parameters (Å, º) top

C1—C12	1.521 (3)	C9—C10	1.326 (4)
C1—C2	1.522 (3)	C9—H9	0.9300
C1—C3	1.534 (3)	C10—C13	1.506 (4)
C1—C8	1.535 (3)	C10—C11	1.513 (4)
C2—C3	1.507 (4)	C11—O1	1.442 (3)
C2—Cl2	1.764 (3)	C11—C12	1.524 (4)
C2—Cl1	1.771 (3)	C11—H11	0.9800
C3—C14	1.524 (4)	C12—H12A	0.9700
C3—C4	1.535 (4)	C12—H12B	0.9700
C4—C5	1.512 (5)	C13—H13A	0.9600
C4—H4A	0.9700	C13—H13B	0.9600
C4—H4B	0.9700	C13—H13C	0.9600
C5—C6	1.584 (5)	C14—H14A	0.9600
C5—H5A	0.9700	C14—H14B	0.9600
C5—H5B	0.9700	C14—H14C	0.9600
C6—C7	1.518 (5)	C15—H15A	0.9600
C6—H6A	0.9700	C15—H15B	0.9600
C6—H6B	0.9700	C15—H15C	0.9600
C7—C15	1.534 (5)	C16—H16A	0.9600
C7—C16	1.545 (5)	C16—H16B	0.9600
C7—C8	1.585 (4)	C16—H16C	0.9600
C8—C9	1.505 (3)	O1—H1	0.8200
C8—H8	0.9800

C12—C1—C2	117.7 (2)	C1—C8—H8	106.2
C12—C1—C3	121.6 (2)	C7—C8—H8	106.2
C2—C1—C3	59.08 (17)	C10—C9—C8	126.2 (2)
C12—C1—C8	112.3 (2)	C10—C9—H9	116.9
C2—C1—C8	118.1 (2)	C8—C9—H9	116.9
C3—C1—C8	118.4 (2)	C9—C10—C13	123.3 (3)
C3—C2—C1	60.86 (17)	C9—C10—C11	121.5 (2)
C3—C2—Cl2	119.6 (2)	C13—C10—C11	115.2 (2)
C1—C2—Cl2	119.77 (19)	O1—C11—C10	110.7 (2)
C3—C2—Cl1	120.9 (2)	O1—C11—C12	107.7 (2)
C1—C2—Cl1	120.59 (18)	C10—C11—C12	112.9 (2)
Cl2—C2—Cl1	108.61 (15)	O1—C11—H11	108.5
C2—C3—C14	118.9 (3)	C10—C11—H11	108.5
C2—C3—C1	60.06 (16)	C12—C11—H11	108.5
C14—C3—C1	120.3 (3)	C1—C12—C11	110.3 (2)
C2—C3—C4	118.3 (2)	C1—C12—H12A	109.6
C14—C3—C4	113.0 (3)	C11—C12—H12A	109.6
C1—C3—C4	116.7 (2)	C1—C12—H12B	109.6
C5—C4—C3	112.2 (3)	C11—C12—H12B	109.6
C5—C4—H4A	109.2	H12A—C12—H12B	108.1
C3—C4—H4A	109.2	C10—C13—H13A	109.5
C5—C4—H4B	109.2	C10—C13—H13B	109.5
C3—C4—H4B	109.2	H13A—C13—H13B	109.5
H4A—C4—H4B	107.9	C10—C13—H13C	109.5
C4—C5—C6	114.6 (3)	H13A—C13—H13C	109.5
C4—C5—H5A	108.6	H13B—C13—H13C	109.5
C6—C5—H5A	108.6	C3—C14—H14A	109.5
C4—C5—H5B	108.6	C3—C14—H14B	109.5
C6—C5—H5B	108.6	H14A—C14—H14B	109.5
H5A—C5—H5B	107.6	C3—C14—H14C	109.5
C7—C6—C5	118.0 (3)	H14A—C14—H14C	109.5
C7—C6—H6A	107.8	H14B—C14—H14C	109.5
C5—C6—H6A	107.8	C7—C15—H15A	109.5
C7—C6—H6B	107.8	C7—C15—H15B	109.5
C5—C6—H6B	107.8	H15A—C15—H15B	109.5
H6A—C6—H6B	107.2	C7—C15—H15C	109.5
C6—C7—C15	111.2 (3)	H15A—C15—H15C	109.5
C6—C7—C16	108.2 (3)	H15B—C15—H15C	109.5
C15—C7—C16	106.2 (3)	C7—C16—H16A	109.5
C6—C7—C8	112.8 (2)	C7—C16—H16B	109.5
C15—C7—C8	107.1 (3)	H16A—C16—H16B	109.5
C16—C7—C8	111.1 (3)	C7—C16—H16C	109.5
C9—C8—C1	109.4 (2)	H16A—C16—H16C	109.5
C9—C8—C7	113.1 (2)	H16B—C16—H16C	109.5
C1—C8—C7	115.0 (2)	C11—O1—H1	109.5
C9—C8—H8	106.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ⁱ	0.82	2.10	2.853 (4)	153

Symmetry code: (i) −y+2, x−y, z−1/3.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₄Cl₂O
M_r	303.25
Crystal system, space group	Trigonal, P3₂
Temperature (K)	298
a, c (Å)	13.2323 (13), 7.9807 (8)
V (Å³)	1210.2 (2)
Z	3
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.41 × 0.33 × 0.26

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8123, 3135, 2995
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.126, 1.09
No. of reflections	3135
No. of parameters	180
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.33
Absolute structure	Flack & Bernardinelli (2000), 1940 Friedel pairs
Absolute structure parameter	−0.11 (7)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1ⁱ	0.820	2.10	2.853 (4)	153

Symmetry code: (i) −y+2, x−y, z−1/3.

Acknowledgements

We thank the National Center of Scientific and Technological Research (CNRST) which supports our scientific research.

References

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Volume 67| Part 3| March 2011| Page o615

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(1S,3R,8R,11S)-2,2-Di­chloro-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.01,3]dodec-9-en-11-ol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1S,3R,8R,11S)-2,2-Dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-9-en-11-ol