(1R,4R,6S,7S)-5,5-Di­chloro-1,4,8,8-tetra­methyl­tri­cyclo­[5.4.11,7.04,6]dodecan-12-one

Benharref, A.; EL Karroumi, J.; Daran, J.-C.; Berraho, M.

doi:10.1107/S1600536813028791

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page o1703

doi:10.1107/S1600536813028791

Open

access

(1R,4R,6S,7S)-5,5-Dichloro-1,4,8,8-tetramethyltricyclo[5.4.1^1,7.0^4,6]dodecan-12-one

Ahmed Benharref,^a Jamal EL Karroumi,^a ^* Jean-Claude Daran ^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 ^bLaboratoire de Chimie de Coordination, 205 Route de Narbone, 31077 Toulouse Cedex 04, France
^*Correspondence e-mail: berraho@uca.ma

(Received 7 October 2013; accepted 20 October 2013; online 26 October 2013)

The title compound, C₁₆H₂₄Cl₂O, was synthesized in three steps 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 asymmetric unit contains two independent molecules with similar conformations. Each molecule is built up from two fused seven-membered rings and an additional three-membered ring arising from the reaction of himachalene with dichlorocarbene. The dihedral angles between the mean planes of the two seven-membered rings are 75.03 (9) and 75.02 (9)° in the two independent molecules.

CCDC reference: 967472

Related literature

For the reactivity of this sesquiterpene, see: El Jamili et al. (2002 ); Lassaba et al. (1997 ). For its biological activity, see: Elhaib et al. (2011 ). For a related structure, see: Benharref et al. (2013 ). For conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₆H₂₄Cl₂O
M_r = 303.25
Triclinic, P 1
a = 6.5835 (2) Å
b = 9.2584 (3) Å
c = 12.8428 (5) Å
α = 85.140 (3)°
β = 84.795 (3)°
γ = 89.067 (3)°
V = 776.74 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 180 K
0.50 × 0.03 × 0.03 mm

Data collection

Agilent Xcalibur (Eos, Gemini ultra) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ) T_min = 0.822, T_max = 0.988
15959 measured reflections
6301 independent reflections
5899 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.070
S = 1.05
6301 reflections
351 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack & Bernardinelli (2000 ), 3127 Friedel pairs
Absolute structure parameter: 0.05 (3)

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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).

Supporting information

CCDC reference: 967472

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813028791/bt6937sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028791/bt6937Isup2.hkl

checkCIF report

Comment top

Our work lies within the framework of the valorization of the most abundant essential oils in Morocco, such as Cedrus atlantica. This oil is made up mainly (75%) of bicyclic sesquiterpenes hydrocarbons, among which is found the compound β-himachalene (Elhaib et al., 2011). The reactivity of this sesquiterpene has been studied extensively by our team, in order to prepare new products having olfactive proprieties suitable for the perfume or cosmetics industry (El Jamili et al., 2002; Benharref et al., 2013). In this paper we present the crystal structure of the title compound, (1R,4R, 6S, 7S)-5,5-dichloro-1,4,8,8- tetramethyl-tricyclo[5.4.1¹,⁷.0⁴,⁶]dodecan-12-one. The asymmetric unit of the title compound contains two independent molecules of similar geometry (Fig. 1). Each molecule contains two fused seven-membered rings, which are fused to a three-membered ring as shown in Fig. 1. In both molecules, one of the seven-membered ring has a chair conformation as indicated by the total puckering amplitude QT = 0.8377 (3) Å and spherical polar angle θ2 = 38.51 (13)° with ϕ2 = -100.60 (20)°, ϕ3 = 93.49 (18), whereas the other seven-membered ring displays screw boat conformation with QT = 1.0334 (20) Å, θ2 = 75.83 (10)°, ϕ2 = 151.23 (10)° and ϕ3 =119.77 (5)° (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(R), C4(R), C6(S) and C7(S).

Related literature top

For the reactivity of this sesquiterpene, see: El Jamili et al. (2002); Lassaba et al. (1997). For its biological activity, see: Elhaib et al. (2011). For a related structure, see: Benharref et al. (2013). For conformational analysis, see: Cremer & Pople (1975).

Experimental top

To obtain the title compound, BF₃—Et₂O (1 mL) was added dropwise to a solution of (1S,3R,8S)-2,2-dichloro- 3,7,7,10- tetramethyltricyclo [6.4.0.0¹,³]dodec-9-ene (Lassaba et al., 1997) (1 g, 3.3 mmol) in 60 ml of dichloromethane at 195 K under nitrogen. The reaction mixture was stirred for two hours at a constant temperature of 195 K and the left at ambient temperature for 24 h. Water (60 ml) was added in order to separate the two phases, and the organic phase was dried and concentrated. The residue obtained was chromatographed on silica-gel eluting with hexane-ethyle acetate (97/3), which allowed the isolation of pure(1R,4R, 6S, 7S)-1,4,8,8- tetramethyltricyclo[5.4.1¹,⁷.0⁴,⁶]dodecan-12-one in a yield of 77% (755 mg, 2.5 mmol). The title compound was recrystallized from its hexane solution.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); 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. : 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.

(1R,4R,6S,7S)-5,5-Dichloro-1,4,8,8-tetramethyltricyclo[5.4.1^1,7.0^4,6]dodecan-12-one top

Crystal data top

C₁₆H₂₄Cl₂O	Z = 2
M_r = 303.25	F(000) = 324
Triclinic, P1	D_x = 1.297 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5835 (2) Å	Cell parameters from 6301 reflections
b = 9.2584 (3) Å	θ = 3.1–26.4°
c = 12.8428 (5) Å	µ = 0.41 mm⁻¹
α = 85.140 (3)°	T = 180 K
β = 84.795 (3)°	Needle, colourless
γ = 89.067 (3)°	0.50 × 0.03 × 0.03 mm
V = 776.74 (5) Å³

Data collection top

Agilent Xcalibur (Eos, Gemini ultra) diffractometer	6301 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5899 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 16.1978 pixels mm^-1	θ_max = 26.4°, θ_min = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −11→11
T_min = 0.822, T_max = 0.988	l = −16→16
15959 measured reflections

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)] = 0.030	H-atom parameters constrained
wR(F²) = 0.070	w = 1/[σ²(F_o²) + (0.0384P)² + 0.0135P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
6301 reflections	Δρ_max = 0.19 e Å⁻³
351 parameters	Δρ_min = −0.15 e Å⁻³
3 restraints	Absolute structure: Flack & Bernardinelli (2000), 3127 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (3)

Crystal data top

C₁₆H₂₄Cl₂O	γ = 89.067 (3)°
M_r = 303.25	V = 776.74 (5) Å³
Triclinic, P1	Z = 2
a = 6.5835 (2) Å	Mo Kα radiation
b = 9.2584 (3) Å	µ = 0.41 mm⁻¹
c = 12.8428 (5) Å	T = 180 K
α = 85.140 (3)°	0.50 × 0.03 × 0.03 mm
β = 84.795 (3)°

Data collection top

Agilent Xcalibur (Eos, Gemini ultra) diffractometer	6301 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	5899 reflections with I > 2σ(I)
T_min = 0.822, T_max = 0.988	R_int = 0.030
15959 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.070	Δρ_max = 0.19 e Å⁻³
S = 1.05	Δρ_min = −0.15 e Å⁻³
6301 reflections	Absolute structure: Flack & Bernardinelli (2000), 3127 Friedel pairs
351 parameters	Absolute structure parameter: 0.05 (3)
3 restraints

Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Agilent Technologies, 2013 )

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
Cl2	−0.55173 (7)	0.67043 (6)	0.24182 (4)	0.03779 (14)
Cl1	−0.12276 (7)	0.65390 (5)	0.27094 (4)	0.03107 (12)
O1	0.1568 (2)	1.00986 (16)	0.33958 (12)	0.0348 (3)
C7	−0.1944 (3)	0.95465 (19)	0.37125 (14)	0.0200 (4)
H7	−0.1351	0.8613	0.4003	0.024*
C6	−0.3450 (3)	0.9136 (2)	0.29500 (14)	0.0203 (4)
H6	−0.4889	0.9435	0.3151	0.024*
C5	−0.3277 (3)	0.7716 (2)	0.24622 (14)	0.0228 (4)
C4	−0.2947 (3)	0.9096 (2)	0.17593 (14)	0.0222 (4)
C3	−0.0806 (3)	0.9470 (2)	0.12878 (15)	0.0249 (4)
H3A	−0.0648	0.9194	0.0557	0.030*
H3B	0.0180	0.8884	0.1687	0.030*
C2	−0.0269 (3)	1.1079 (2)	0.12843 (15)	0.0276 (4)
H2A	−0.1161	1.1651	0.0821	0.033*
H2B	0.1154	1.1214	0.0974	0.033*
C1	−0.0476 (3)	1.1710 (2)	0.23755 (16)	0.0257 (4)
C11	−0.2564 (3)	1.2460 (2)	0.25562 (15)	0.0257 (4)
H11A	−0.2569	1.3356	0.2078	0.031*
H11B	−0.3620	1.1814	0.2354	0.031*
C10	−0.3185 (3)	1.2863 (2)	0.36775 (16)	0.0307 (4)
H10A	−0.1950	1.3134	0.3999	0.037*
H10B	−0.4103	1.3720	0.3646	0.037*
C9	−0.4261 (3)	1.1633 (2)	0.43734 (15)	0.0268 (4)
H9A	−0.5422	1.1321	0.4011	0.032*
H9B	−0.4837	1.2034	0.5029	0.032*
C8	−0.3000 (3)	1.0280 (2)	0.46780 (14)	0.0241 (4)
C12	−0.0146 (3)	1.0435 (2)	0.31871 (14)	0.0229 (4)
C14	−0.4603 (3)	0.9581 (2)	0.10671 (16)	0.0324 (5)
H14A	−0.4543	0.8990	0.0467	0.049*
H14B	−0.4405	1.0602	0.0815	0.049*
H14C	−0.5936	0.9465	0.1469	0.049*
C13	0.1222 (3)	1.2827 (2)	0.24143 (18)	0.0357 (5)
H13A	0.1108	1.3212	0.3105	0.054*
H13B	0.1080	1.3621	0.1870	0.054*
H13C	0.2556	1.2356	0.2292	0.054*
C16	−0.1382 (3)	1.0656 (2)	0.53919 (17)	0.0349 (5)
H16A	−0.2048	1.1053	0.6021	0.052*
H16B	−0.0451	1.1378	0.5015	0.052*
H16C	−0.0612	0.9780	0.5597	0.052*
C15	−0.4447 (3)	0.9173 (2)	0.52973 (16)	0.0332 (5)
H15A	−0.5086	0.9592	0.5923	0.050*
H15B	−0.3675	0.8299	0.5509	0.050*
H15C	−0.5504	0.8919	0.4856	0.050*
Cl3	−0.18678 (7)	0.88753 (6)	0.83571 (4)	0.03989 (14)
Cl4	0.25097 (7)	0.90785 (5)	0.82503 (4)	0.03505 (13)
O2	0.5852 (2)	0.54459 (17)	0.75362 (12)	0.0367 (4)
C22	0.2470 (3)	0.6078 (2)	0.71903 (14)	0.0216 (4)
H22	0.3155	0.7015	0.6938	0.026*
C23	0.0593 (3)	0.6475 (2)	0.79047 (13)	0.0203 (4)
H23	−0.0722	0.6174	0.7658	0.024*
C24	0.0441 (3)	0.7881 (2)	0.84020 (15)	0.0255 (4)
C25	0.0528 (3)	0.6489 (2)	0.91026 (14)	0.0235 (4)
C26	0.2462 (3)	0.6118 (2)	0.96257 (16)	0.0292 (5)
H26A	0.2271	0.6376	1.0361	0.035*
H26B	0.3590	0.6713	0.9262	0.035*
C27	0.3070 (3)	0.4512 (2)	0.96203 (15)	0.0305 (5)
H27A	0.1995	0.3934	1.0048	0.037*
H27B	0.4343	0.4364	0.9972	0.037*
C17	0.3412 (3)	0.3893 (2)	0.85254 (16)	0.0281 (4)
C18	0.1452 (3)	0.3153 (2)	0.82720 (15)	0.0273 (4)
H18A	0.1271	0.2242	0.8732	0.033*
H18B	0.0276	0.3793	0.8450	0.033*
C19	0.1398 (3)	0.2793 (2)	0.71244 (16)	0.0316 (5)
H19A	0.2795	0.2545	0.6839	0.038*
H19B	0.0535	0.1931	0.7109	0.038*
C20	0.0575 (3)	0.4033 (2)	0.64249 (15)	0.0283 (4)
H20A	−0.0769	0.4324	0.6756	0.034*
H20B	0.0337	0.3654	0.5749	0.034*
C21	0.1874 (3)	0.54054 (19)	0.61824 (14)	0.0241 (4)
C28	0.4060 (3)	0.5151 (2)	0.77276 (15)	0.0250 (4)
C30	−0.1408 (3)	0.5985 (2)	0.97438 (16)	0.0342 (5)
H30A	−0.1600	0.6509	1.0378	0.051*
H30B	−0.1307	0.4942	0.9943	0.051*
H30C	−0.2572	0.6176	0.9327	0.051*
C29	0.5159 (3)	0.2754 (3)	0.8552 (2)	0.0421 (6)
H29A	0.5316	0.2304	0.7885	0.063*
H29B	0.4834	0.2009	0.9128	0.063*
H29C	0.6434	0.3230	0.8658	0.063*
C32	0.0631 (3)	0.6546 (2)	0.55706 (16)	0.0352 (5)
H32A	0.0281	0.6166	0.4921	0.053*
H32B	0.1440	0.7427	0.5400	0.053*
H32C	−0.0622	0.6773	0.6000	0.053*
C31	0.3815 (3)	0.5080 (2)	0.54861 (17)	0.0367 (5)
H31A	0.4638	0.4351	0.5860	0.055*
H31B	0.4604	0.5971	0.5317	0.055*
H31C	0.3444	0.4711	0.4837	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.0375 (3)	0.0381 (3)	0.0399 (3)	−0.0163 (2)	−0.0103 (2)	−0.0053 (2)
Cl1	0.0392 (3)	0.0217 (3)	0.0338 (3)	0.00646 (19)	−0.0096 (2)	−0.0054 (2)
O1	0.0234 (8)	0.0372 (9)	0.0440 (9)	0.0007 (6)	−0.0064 (6)	−0.0013 (7)
C7	0.0211 (9)	0.0178 (9)	0.0215 (9)	−0.0003 (7)	−0.0036 (7)	−0.0023 (7)
C6	0.0187 (9)	0.0205 (10)	0.0217 (9)	0.0014 (7)	−0.0008 (7)	−0.0024 (7)
C5	0.0226 (9)	0.0233 (10)	0.0239 (9)	−0.0027 (8)	−0.0072 (8)	−0.0043 (8)
C4	0.0231 (9)	0.0236 (10)	0.0207 (9)	0.0010 (7)	−0.0045 (7)	−0.0037 (7)
C3	0.0266 (10)	0.0281 (11)	0.0198 (9)	0.0024 (8)	0.0023 (7)	−0.0048 (8)
C2	0.0272 (10)	0.0291 (11)	0.0247 (10)	0.0011 (8)	0.0041 (8)	0.0006 (8)
C1	0.0276 (10)	0.0224 (10)	0.0261 (9)	0.0000 (7)	0.0010 (7)	−0.0008 (8)
C11	0.0278 (10)	0.0203 (10)	0.0275 (10)	0.0032 (7)	0.0013 (8)	0.0024 (8)
C10	0.0367 (11)	0.0198 (10)	0.0340 (11)	0.0047 (8)	0.0058 (9)	−0.0028 (8)
C9	0.0310 (10)	0.0242 (10)	0.0245 (10)	0.0019 (8)	0.0064 (8)	−0.0068 (8)
C8	0.0293 (10)	0.0219 (9)	0.0211 (9)	−0.0032 (8)	0.0009 (7)	−0.0044 (8)
C12	0.0234 (10)	0.0230 (9)	0.0233 (9)	0.0013 (7)	−0.0018 (7)	−0.0083 (8)
C14	0.0314 (11)	0.0407 (12)	0.0257 (10)	0.0055 (9)	−0.0076 (8)	−0.0023 (9)
C13	0.0351 (11)	0.0317 (12)	0.0381 (12)	−0.0075 (9)	0.0057 (9)	0.0014 (10)
C16	0.0458 (13)	0.0327 (12)	0.0284 (11)	−0.0061 (10)	−0.0076 (9)	−0.0091 (9)
C15	0.0411 (12)	0.0299 (11)	0.0279 (10)	−0.0047 (9)	0.0017 (9)	−0.0015 (9)
Cl3	0.0376 (3)	0.0456 (3)	0.0363 (3)	0.0189 (2)	0.0002 (2)	−0.0097 (2)
Cl4	0.0410 (3)	0.0226 (3)	0.0418 (3)	−0.0059 (2)	−0.0005 (2)	−0.0072 (2)
O2	0.0224 (7)	0.0427 (9)	0.0443 (9)	−0.0031 (6)	0.0003 (6)	−0.0027 (7)
C22	0.0211 (9)	0.0196 (9)	0.0240 (9)	−0.0014 (7)	0.0003 (7)	−0.0042 (8)
C23	0.0198 (9)	0.0224 (10)	0.0195 (9)	0.0000 (7)	−0.0032 (7)	−0.0051 (7)
C24	0.0247 (10)	0.0258 (10)	0.0260 (10)	0.0028 (8)	0.0010 (8)	−0.0071 (8)
C25	0.0257 (9)	0.0249 (10)	0.0208 (9)	−0.0028 (8)	−0.0023 (7)	−0.0067 (8)
C26	0.0347 (11)	0.0326 (12)	0.0221 (10)	−0.0056 (9)	−0.0088 (8)	−0.0051 (9)
C27	0.0364 (11)	0.0334 (12)	0.0223 (10)	−0.0049 (9)	−0.0103 (8)	0.0036 (9)
C17	0.0316 (11)	0.0239 (10)	0.0289 (11)	−0.0029 (8)	−0.0048 (8)	0.0000 (8)
C18	0.0320 (10)	0.0207 (10)	0.0288 (10)	−0.0062 (8)	−0.0037 (8)	0.0025 (8)
C19	0.0410 (12)	0.0197 (10)	0.0356 (11)	−0.0063 (9)	−0.0101 (9)	−0.0022 (9)
C20	0.0364 (11)	0.0237 (10)	0.0265 (10)	−0.0046 (8)	−0.0072 (8)	−0.0068 (8)
C21	0.0296 (10)	0.0222 (10)	0.0203 (9)	0.0024 (8)	−0.0001 (7)	−0.0036 (8)
C28	0.0245 (10)	0.0264 (10)	0.0251 (9)	−0.0020 (8)	−0.0016 (7)	−0.0086 (8)
C30	0.0348 (12)	0.0443 (13)	0.0230 (10)	−0.0085 (10)	0.0036 (8)	−0.0053 (9)
C29	0.0418 (13)	0.0338 (13)	0.0515 (15)	0.0034 (10)	−0.0157 (11)	0.0037 (11)
C32	0.0481 (13)	0.0315 (12)	0.0263 (11)	0.0062 (10)	−0.0071 (9)	−0.0011 (9)
C31	0.0466 (13)	0.0309 (12)	0.0312 (11)	0.0065 (9)	0.0081 (9)	−0.0078 (9)

Geometric parameters (Å, º) top

Cl2—C5	1.7679 (18)	Cl3—C24	1.7669 (19)
Cl1—C5	1.7553 (19)	Cl4—C24	1.757 (2)
O1—C12	1.213 (2)	O2—C28	1.214 (2)
C7—C12	1.525 (2)	C22—C28	1.520 (3)
C7—C6	1.529 (2)	C22—C23	1.530 (2)
C7—C8	1.566 (2)	C22—C21	1.566 (2)
C7—H7	1.0000	C22—H22	1.0000
C6—C5	1.502 (3)	C23—C24	1.496 (3)
C6—C4	1.538 (2)	C23—C25	1.536 (2)
C6—H6	1.0000	C23—H23	1.0000
C5—C4	1.507 (3)	C24—C25	1.512 (3)
C4—C14	1.507 (3)	C25—C30	1.511 (3)
C4—C3	1.516 (3)	C25—C26	1.514 (3)
C3—C2	1.536 (3)	C26—C27	1.534 (3)
C3—H3A	0.9900	C26—H26A	0.9900
C3—H3B	0.9900	C26—H26B	0.9900
C2—C1	1.557 (3)	C27—C17	1.559 (3)
C2—H2A	0.9900	C27—H27A	0.9900
C2—H2B	0.9900	C27—H27B	0.9900
C1—C12	1.533 (3)	C17—C28	1.524 (3)
C1—C11	1.538 (3)	C17—C18	1.543 (3)
C1—C13	1.542 (3)	C17—C29	1.548 (3)
C11—C10	1.536 (3)	C18—C19	1.542 (3)
C11—H11A	0.9900	C18—H18A	0.9900
C11—H11B	0.9900	C18—H18B	0.9900
C10—C9	1.528 (3)	C19—C20	1.520 (3)
C10—H10A	0.9900	C19—H19A	0.9900
C10—H10B	0.9900	C19—H19B	0.9900
C9—C8	1.534 (3)	C20—C21	1.537 (3)
C9—H9A	0.9900	C20—H20A	0.9900
C9—H9B	0.9900	C20—H20B	0.9900
C8—C16	1.530 (3)	C21—C32	1.533 (3)
C8—C15	1.532 (3)	C21—C31	1.533 (3)
C14—H14A	0.9800	C30—H30A	0.9800
C14—H14B	0.9800	C30—H30B	0.9800
C14—H14C	0.9800	C30—H30C	0.9800
C13—H13A	0.9800	C29—H29A	0.9800
C13—H13B	0.9800	C29—H29B	0.9800
C13—H13C	0.9800	C29—H29C	0.9800
C16—H16A	0.9800	C32—H32A	0.9800
C16—H16B	0.9800	C32—H32B	0.9800
C16—H16C	0.9800	C32—H32C	0.9800
C15—H15A	0.9800	C31—H31A	0.9800
C15—H15B	0.9800	C31—H31B	0.9800
C15—H15C	0.9800	C31—H31C	0.9800

C12—C7—C6	113.69 (15)	C28—C22—C23	115.15 (15)
C12—C7—C8	111.45 (14)	C28—C22—C21	111.30 (14)
C6—C7—C8	113.02 (14)	C23—C22—C21	112.01 (14)
C12—C7—H7	106.0	C28—C22—H22	105.9
C6—C7—H7	106.0	C23—C22—H22	105.9
C8—C7—H7	106.0	C21—C22—H22	105.9
C5—C6—C7	121.40 (15)	C24—C23—C22	121.73 (16)
C5—C6—C4	59.44 (12)	C24—C23—C25	59.80 (12)
C7—C6—C4	124.80 (15)	C22—C23—C25	124.79 (15)
C5—C6—H6	113.6	C24—C23—H23	113.4
C7—C6—H6	113.6	C22—C23—H23	113.4
C4—C6—H6	113.6	C25—C23—H23	113.4
C6—C5—C4	61.49 (12)	C23—C24—C25	61.44 (12)
C6—C5—Cl1	119.70 (13)	C23—C24—Cl4	120.37 (13)
C4—C5—Cl1	120.64 (13)	C25—C24—Cl4	120.24 (14)
C6—C5—Cl2	118.54 (14)	C23—C24—Cl3	117.87 (13)
C4—C5—Cl2	119.57 (13)	C25—C24—Cl3	120.13 (14)
Cl1—C5—Cl2	109.78 (10)	Cl4—C24—Cl3	109.71 (11)
C14—C4—C5	117.78 (16)	C30—C25—C24	117.93 (17)
C14—C4—C3	114.32 (16)	C30—C25—C26	114.40 (16)
C5—C4—C3	118.95 (16)	C24—C25—C26	118.76 (16)
C14—C4—C6	117.05 (16)	C30—C25—C23	117.56 (16)
C5—C4—C6	59.06 (12)	C24—C25—C23	58.77 (12)
C3—C4—C6	118.82 (15)	C26—C25—C23	118.41 (16)
C4—C3—C2	114.24 (16)	C25—C26—C27	113.38 (16)
C4—C3—H3A	108.7	C25—C26—H26A	108.9
C2—C3—H3A	108.7	C27—C26—H26A	108.9
C4—C3—H3B	108.7	C25—C26—H26B	108.9
C2—C3—H3B	108.7	C27—C26—H26B	108.9
H3A—C3—H3B	107.6	H26A—C26—H26B	107.7
C3—C2—C1	115.69 (15)	C26—C27—C17	116.55 (16)
C3—C2—H2A	108.4	C26—C27—H27A	108.2
C1—C2—H2A	108.4	C17—C27—H27A	108.2
C3—C2—H2B	108.4	C26—C27—H27B	108.2
C1—C2—H2B	108.4	C17—C27—H27B	108.2
H2A—C2—H2B	107.4	H27A—C27—H27B	107.3
C12—C1—C11	113.36 (16)	C28—C17—C18	112.73 (15)
C12—C1—C13	108.50 (16)	C28—C17—C29	108.98 (17)
C11—C1—C13	109.14 (16)	C18—C17—C29	108.93 (17)
C12—C1—C2	106.37 (15)	C28—C17—C27	107.26 (16)
C11—C1—C2	110.02 (16)	C18—C17—C27	110.05 (16)
C13—C1—C2	109.37 (16)	C29—C17—C27	108.80 (17)
C10—C11—C1	116.28 (17)	C19—C18—C17	115.65 (17)
C10—C11—H11A	108.2	C19—C18—H18A	108.4
C1—C11—H11A	108.2	C17—C18—H18A	108.4
C10—C11—H11B	108.2	C19—C18—H18B	108.4
C1—C11—H11B	108.2	C17—C18—H18B	108.4
H11A—C11—H11B	107.4	H18A—C18—H18B	107.4
C9—C10—C11	113.05 (16)	C20—C19—C18	113.13 (17)
C9—C10—H10A	109.0	C20—C19—H19A	109.0
C11—C10—H10A	109.0	C18—C19—H19A	109.0
C9—C10—H10B	109.0	C20—C19—H19B	109.0
C11—C10—H10B	109.0	C18—C19—H19B	109.0
H10A—C10—H10B	107.8	H19A—C19—H19B	107.8
C10—C9—C8	117.89 (16)	C19—C20—C21	118.06 (16)
C10—C9—H9A	107.8	C19—C20—H20A	107.8
C8—C9—H9A	107.8	C21—C20—H20A	107.8
C10—C9—H9B	107.8	C19—C20—H20B	107.8
C8—C9—H9B	107.8	C21—C20—H20B	107.8
H9A—C9—H9B	107.2	H20A—C20—H20B	107.1
C16—C8—C15	108.00 (16)	C32—C21—C31	107.83 (16)
C16—C8—C9	110.18 (16)	C32—C21—C20	108.17 (16)
C15—C8—C9	107.78 (16)	C31—C21—C20	110.29 (16)
C16—C8—C7	109.33 (15)	C32—C21—C22	107.76 (15)
C15—C8—C7	107.83 (15)	C31—C21—C22	109.32 (15)
C9—C8—C7	113.54 (14)	C20—C21—C22	113.29 (15)
O1—C12—C7	119.24 (17)	O2—C28—C22	119.31 (17)
O1—C12—C1	119.90 (17)	O2—C28—C17	120.21 (17)
C7—C12—C1	120.83 (15)	C22—C28—C17	120.45 (15)
C4—C14—H14A	109.5	C25—C30—H30A	109.5
C4—C14—H14B	109.5	C25—C30—H30B	109.5
H14A—C14—H14B	109.5	H30A—C30—H30B	109.5
C4—C14—H14C	109.5	C25—C30—H30C	109.5
H14A—C14—H14C	109.5	H30A—C30—H30C	109.5
H14B—C14—H14C	109.5	H30B—C30—H30C	109.5
C1—C13—H13A	109.5	C17—C29—H29A	109.5
C1—C13—H13B	109.5	C17—C29—H29B	109.5
H13A—C13—H13B	109.5	H29A—C29—H29B	109.5
C1—C13—H13C	109.5	C17—C29—H29C	109.5
H13A—C13—H13C	109.5	H29A—C29—H29C	109.5
H13B—C13—H13C	109.5	H29B—C29—H29C	109.5
C8—C16—H16A	109.5	C21—C32—H32A	109.5
C8—C16—H16B	109.5	C21—C32—H32B	109.5
H16A—C16—H16B	109.5	H32A—C32—H32B	109.5
C8—C16—H16C	109.5	C21—C32—H32C	109.5
H16A—C16—H16C	109.5	H32A—C32—H32C	109.5
H16B—C16—H16C	109.5	H32B—C32—H32C	109.5
C8—C15—H15A	109.5	C21—C31—H31A	109.5
C8—C15—H15B	109.5	C21—C31—H31B	109.5
H15A—C15—H15B	109.5	H31A—C31—H31B	109.5
C8—C15—H15C	109.5	C21—C31—H31C	109.5
H15A—C15—H15C	109.5	H31A—C31—H31C	109.5
H15B—C15—H15C	109.5	H31B—C31—H31C	109.5

Experimental details

Crystal data
Chemical formula	C₁₆H₂₄Cl₂O
M_r	303.25
Crystal system, space group	Triclinic, P1
Temperature (K)	180
a, b, c (Å)	6.5835 (2), 9.2584 (3), 12.8428 (5)
α, β, γ (°)	85.140 (3), 84.795 (3), 89.067 (3)
V (Å³)	776.74 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.50 × 0.03 × 0.03

Data collection
Diffractometer	Agilent Xcalibur (Eos, Gemini ultra) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013)
T_min, T_max	0.822, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	15959, 6301, 5899
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.070, 1.05
No. of reflections	6301
No. of parameters	351
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15
Absolute structure	Flack & Bernardinelli (2000), 3127 Friedel pairs
Absolute structure parameter	0.05 (3)

Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

References

Agilent (2013). CrysAlis PRO . Agilent Technologies Ltd, Yarnton, England. Google Scholar
Benharref, A., Ourhriss, N., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o933–o934. CSD CrossRef CAS IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Elhaib, A., Benharref, A., Parrès-Maynadié, S., Manoury, E., Urrutigoïty, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101–108. CAS Google Scholar
El Jamili, H., Auhmani, A., Dakir, M., Lassaba, E., Benharref, A., Pierrot, M., Chiaroni, A. & Riche, C. (2002). Tetrahedron Lett. 43, 6645–6648. CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143–1148. Web of Science CrossRef CAS IUCr Journals Google Scholar
Lassaba, E., Benharref, A., Giorgi, M. & Pierrot, M. (1997). Acta Cryst. C53, 1943–1945. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.