(1S,3R,8R,10R)-2,2-Di­bromo-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.01,3]dodecan-9-one

Benharref, A.; Mazoir, N.; Daran, J.-C.; Berraho, M.

doi:10.1107/S1600536813030936

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1777-o1778

doi:10.1107/S1600536813030936

Open

access

(1S,3R,8R,10R)-2,2-Dibromo-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodecan-9-one

Ahmed Benharref,^a Noureddine Mazoir,^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 6 November 2013; accepted 11 November 2013; online 16 November 2013)

The title compound, C₁₆H₂₄Br₂O was synthesized by 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 molecule is built up from a seven-membered ring to which a six- and a three-membered ring are fused. The six-membered ring shows a chair conformation. One C atom in the seven-membered ring and two methyl groups attached to the ring are disordered over two sets of sites, with an occupancy ratio of 0.658 (7):0.342 (7).

CCDC reference: 971358

Related literature

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

Experimental

Crystal data

C₁₆H₂₄Br₂O
M_r = 392.17
Monoclinic, P 2₁
a = 6.5975 (2) Å
b = 15.2612 (3) Å
c = 8.2688 (2) Å
β = 100.045 (3)°
V = 819.79 (4) Å³
Z = 2
Cu Kα radiation
μ = 6.19 mm⁻¹
T = 180 K
0.5 × 0.03 × 0.03 mm

Data collection

Agilent Xcalibur (Eos, Gemini ultra) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ) T_min = 0.269, T_max = 1.000
6201 measured reflections
2416 independent reflections
2399 reflections with I > 2σ(I)
R_int = 0.021
θ_max = 60.5°

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.057
S = 1.07
2416 reflections
206 parameters
13 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.46 e Å⁻³
Absolute structure: Flack & Bernardinelli (2000 ), 1127 Friedel pairs
Absolute structure parameter: 0.01 (2)

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: 971358

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813030936/bt6944sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813030936/bt6944Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813030936/bt6944Isup3.cml

checkCIF report

Comment top

With the aim exploiting 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 this oil is β-himachalene (El Haib et al., 2011). The reactivity of this sesquiterpene has been studied extensively by our team (El Jamili et al., 2002; Benharref et al., 2013; Ourhriss et al. (2013), in order to prepare new products having olfactive properieties suitable for the perfume or cosmetics industry. In this work we present the crystal structure of the title compound, (1S, 3R, 8R, 10R)-2, 2- dibromo-3,7, 7,10- tetramethyltricyclo[6.4.0.0¹,³]dodecan-9-one. The molecule is built up from two fused seven and six-membered rings and a three-membered ring attached to the seven-membered ring as shown in Fig. 1. The six-membered ring has a chair conformation as indicated by the total puckering amplitude QT = 0.527 (3) Å and spherical polar angle θ = 167.9 (3)° with ϕ = 99.3 (17)° (Cremer & Pople, 1975). Owing to the presence of Br atoms, the absolute configuration could be successfully confirmed as C1(S), C3(R), C8(R) and C10(R).

Related literature top

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

Experimental top

For the synthesis of the compound (1S, 3R, 8R, 10R)-2, 2-dibromo- 3,7,7,10-tetramethyltricyclo [6.4.0.0¹,³]dodecan-9-one, 2 ml of BF₃—Et₂O was added dropwise to a 250 ml flask containing a solution of (1S,3R,8R,9S,10R)-2,2-dibromo- 9α,10α-epoxy- 3,7,7,10-tetramethyltricyclo-[6.4.0.0¹,³]dodecane (Oukhrib et al.,2013) (2 g, 5 mmol) in 100 ml of dichloromethane at 195 K under nitrogen. The reaction mixture was stirred for two hours at a constant temperature of 195 K and was left at ambient temperature for 24 h. Water (60 ml) was a 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 (98/2), which allowed the isolation of pure (1S, 3R, 8R, 10R)-2, 2- dibromo-3,7, 7,10- tetramethyltricyclo[6.4.0.0¹,³]dodecan-9-one in a Yield 80% (1.56 g, 4 mmol). The title compound was recrystallized from its pentane 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. The minor occupied sites of the disordered atoms have been omitted for clarity.

(1S,3R,8R,10R)-2,2-Dibromo-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodecan-9-one top

Crystal data top

C₁₆H₂₄Br₂O	F(000) = 396
M_r = 392.17	D_x = 1.589 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
a = 6.5975 (2) Å	Cell parameters from 5144 reflections
b = 15.2612 (3) Å	θ = 5.4–60.5°
c = 8.2688 (2) Å	µ = 6.19 mm⁻¹
β = 100.045 (3)°	T = 180 K
V = 819.79 (4) Å³	Box, colourless
Z = 2	0.5 × 0.03 × 0.03 mm

Data collection top

Agilent Xcalibur (Eos, Gemini ultra) diffractometer	2416 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2399 reflections with I > 2σ(I)
Miror monochromator	R_int = 0.021
Detector resolution: 16.1978 pixels mm^-1	θ_max = 60.5°, θ_min = 5.4°
ω scans	h = −7→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −17→17
T_min = 0.269, T_max = 1.000	l = −9→9
6201 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)] = 0.022	H-atom parameters constrained
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0402P)² + 0.1798P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2416 reflections	Δρ_max = 0.28 e Å⁻³
206 parameters	Δρ_min = −0.46 e Å⁻³
13 restraints	Absolute structure: Flack & Bernardinelli (2000), 1127 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (2)

Crystal data top

C₁₆H₂₄Br₂O	V = 819.79 (4) Å³
M_r = 392.17	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 6.5975 (2) Å	µ = 6.19 mm⁻¹
b = 15.2612 (3) Å	T = 180 K
c = 8.2688 (2) Å	0.5 × 0.03 × 0.03 mm
β = 100.045 (3)°

Data collection top

Agilent Xcalibur (Eos, Gemini ultra) diffractometer	2416 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	2399 reflections with I > 2σ(I)
T_min = 0.269, T_max = 1.000	R_int = 0.021
6201 measured reflections	θ_max = 60.5°

Refinement top

R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.057	Δρ_max = 0.28 e Å⁻³
S = 1.07	Δρ_min = −0.46 e Å⁻³
2416 reflections	Absolute structure: Flack & Bernardinelli (2000), 1127 Friedel pairs
206 parameters	Absolute structure parameter: 0.01 (2)
13 restraints

Special details top

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

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 > 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	Occ. (<1)
Br1	0.99187 (4)	0.122716 (16)	0.78691 (3)	0.03410 (11)
Br2	0.52030 (5)	0.08850 (2)	0.71788 (4)	0.04828 (14)
C1	0.7175 (4)	0.19420 (18)	1.0114 (3)	0.0248 (5)
C2	0.7326 (4)	0.1623 (2)	0.8397 (3)	0.0291 (6)
C3	0.6907 (5)	0.2575 (2)	0.8643 (3)	0.0326 (7)
C4	0.8580 (6)	0.3239 (2)	0.8543 (4)	0.0410 (8)
H4A	0.8283	0.3534	0.7461	0.049*
H4B	0.9909	0.2928	0.8611	0.049*
C5	0.8797 (7)	0.3936 (2)	0.9896 (4)	0.0503 (9)
H5A	0.7420	0.4081	1.0143	0.060*	0.658 (7)
H5B	0.9391	0.4476	0.9509	0.060*	0.658 (7)
H5C	1.0260	0.4115	1.0157	0.060*	0.342 (7)
H5D	0.7990	0.4457	0.9457	0.060*	0.342 (7)
C6	1.0237 (8)	0.3596 (3)	1.1520 (6)	0.0392 (15)	0.658 (7)
H6A	1.1545	0.3392	1.1218	0.047*	0.658 (7)
H6B	1.0568	0.4102	1.2269	0.047*	0.658 (7)
C7	0.9428 (5)	0.2883 (2)	1.2449 (4)	0.0328 (7)
C14	0.7534 (9)	0.3152 (3)	1.3157 (8)	0.0413 (14)	0.658 (7)
H14A	0.7838	0.3687	1.3809	0.062*	0.658 (7)
H14B	0.7166	0.2682	1.3858	0.062*	0.658 (7)
H14C	0.6383	0.3261	1.2258	0.062*	0.658 (7)
C15	1.1166 (8)	0.2667 (3)	1.3978 (6)	0.0365 (13)	0.658 (7)
H15A	1.2357	0.2410	1.3593	0.055*	0.658 (7)
H15B	1.0630	0.2250	1.4701	0.055*	0.658 (7)
H15C	1.1584	0.3207	1.4585	0.055*	0.658 (7)
C14A	1.1692 (14)	0.3197 (7)	1.2660 (14)	0.045 (3)	0.342 (7)
H14D	1.1823	0.3768	1.3210	0.067*	0.342 (7)
H14E	1.2096	0.3250	1.1579	0.067*	0.342 (7)
H14F	1.2588	0.2772	1.3325	0.067*	0.342 (7)
C15A	0.866 (2)	0.2882 (7)	1.4049 (13)	0.044 (3)	0.342 (7)
H15D	0.9478	0.2471	1.4808	0.065*	0.342 (7)
H15E	0.7213	0.2702	1.3864	0.065*	0.342 (7)
H15F	0.8787	0.3472	1.4521	0.065*	0.342 (7)
C6A	0.8140 (16)	0.3676 (5)	1.1417 (10)	0.039 (3)	0.342 (7)
H6A1	0.6676	0.3499	1.1154	0.047*	0.342 (7)
H6A2	0.8219	0.4196	1.2140	0.047*	0.342 (7)
C8	0.9178 (4)	0.20156 (19)	1.1383 (3)	0.0246 (6)
H8	1.0321	0.2026	1.0731	0.030*
C9	0.9510 (5)	0.1190 (2)	1.2426 (4)	0.0317 (6)
C10	0.7707 (5)	0.07818 (19)	1.3066 (4)	0.0325 (6)
H10	0.7333	0.1186	1.3919	0.039*
C11	0.5854 (5)	0.0733 (2)	1.1673 (4)	0.0360 (7)
H11A	0.6147	0.0305	1.0844	0.043*
H11B	0.4645	0.0519	1.2117	0.043*
C12	0.5341 (4)	0.1611 (2)	1.0847 (4)	0.0324 (6)
H12A	0.5006	0.2040	1.1660	0.039*
H12B	0.4123	0.1550	0.9967	0.039*
C101	0.8255 (6)	−0.0096 (2)	1.3886 (4)	0.0468 (9)
H10A	0.8667	−0.0504	1.3089	0.070*
H10B	0.7056	−0.0331	1.4293	0.070*
H10C	0.9396	−0.0019	1.4808	0.070*
C311	0.4754 (6)	0.2933 (3)	0.7987 (5)	0.0508 (10)
H31A	0.4663	0.3099	0.6832	0.076*
H31B	0.4496	0.3448	0.8628	0.076*
H31C	0.3726	0.2481	0.8081	0.076*
O1	1.1188 (4)	0.08460 (19)	1.2698 (4)	0.0608 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03127 (18)	0.04181 (18)	0.03046 (17)	−0.00328 (14)	0.00880 (13)	−0.00787 (14)
Br2	0.0335 (2)	0.0641 (3)	0.0454 (2)	−0.01004 (16)	0.00180 (17)	−0.02435 (18)
C1	0.0237 (14)	0.0255 (12)	0.0249 (13)	0.0003 (12)	0.0029 (11)	0.0001 (11)
C2	0.0238 (13)	0.0362 (14)	0.0263 (12)	−0.0054 (13)	0.0016 (11)	−0.0060 (12)
C3	0.0347 (16)	0.0360 (15)	0.0258 (13)	0.0046 (13)	0.0011 (12)	0.0022 (12)
C4	0.060 (2)	0.0321 (16)	0.0289 (15)	−0.0066 (15)	0.0024 (15)	0.0089 (13)
C5	0.077 (3)	0.0221 (15)	0.052 (2)	−0.0032 (16)	0.0115 (19)	0.0029 (14)
C6	0.057 (4)	0.023 (2)	0.035 (3)	−0.011 (2)	0.000 (2)	−0.005 (2)
C7	0.0376 (16)	0.0305 (16)	0.0301 (14)	−0.0034 (13)	0.0056 (14)	−0.0104 (13)
C14	0.053 (3)	0.029 (2)	0.042 (3)	0.001 (3)	0.010 (3)	−0.015 (2)
C15	0.044 (3)	0.029 (2)	0.032 (2)	−0.003 (2)	−0.006 (2)	−0.0076 (19)
C14A	0.038 (6)	0.045 (5)	0.052 (6)	−0.010 (5)	0.008 (5)	−0.019 (5)
C15A	0.067 (8)	0.030 (5)	0.037 (6)	−0.008 (5)	0.020 (6)	−0.015 (4)
C6A	0.052 (7)	0.024 (4)	0.045 (5)	0.002 (4)	0.016 (4)	−0.004 (4)
C8	0.0238 (14)	0.0258 (13)	0.0247 (13)	−0.0026 (12)	0.0053 (11)	−0.0044 (11)
C9	0.0354 (16)	0.0320 (14)	0.0267 (12)	0.0054 (16)	0.0027 (12)	−0.0014 (15)
C10	0.0455 (18)	0.0254 (13)	0.0297 (14)	0.0012 (14)	0.0152 (13)	0.0005 (11)
C11	0.0316 (15)	0.0377 (17)	0.0417 (16)	−0.0064 (14)	0.0149 (13)	−0.0003 (14)
C12	0.0224 (14)	0.0378 (14)	0.0379 (14)	−0.0011 (13)	0.0081 (12)	−0.0046 (14)
C101	0.070 (3)	0.0292 (16)	0.0422 (18)	0.0018 (16)	0.0138 (17)	0.0041 (14)
C311	0.048 (2)	0.050 (2)	0.049 (2)	0.0172 (16)	−0.0070 (18)	0.0059 (15)
O1	0.0390 (13)	0.0750 (18)	0.0715 (17)	0.0250 (14)	0.0177 (12)	0.0388 (15)

Geometric parameters (Å, º) top

Br1—C2	1.934 (3)	C15—H15A	0.9800
Br2—C2	1.938 (3)	C15—H15B	0.9800
C1—C2	1.521 (4)	C15—H15C	0.9800
C1—C12	1.530 (4)	C14A—H14D	0.9800
C1—C3	1.539 (4)	C14A—H14E	0.9800
C1—C8	1.542 (4)	C14A—H14F	0.9800
C2—C3	1.499 (4)	C15A—H15D	0.9800
C3—C4	1.512 (5)	C15A—H15E	0.9800
C3—C311	1.530 (4)	C15A—H15F	0.9800
C4—C5	1.533 (5)	C6A—H6A1	0.9900
C4—H4A	0.9900	C6A—H6A2	0.9900
C4—H4B	0.9900	C8—C9	1.521 (4)
C5—C6A	1.455 (9)	C8—H8	1.0000
C5—C6	1.590 (6)	C9—O1	1.210 (4)
C5—H5A	0.9900	C9—C10	1.517 (4)
C5—H5B	0.9900	C10—C101	1.516 (4)
C5—H5C	0.9900	C10—C11	1.528 (4)
C5—H5D	0.9900	C10—H10	1.0000
C6—C7	1.484 (6)	C11—C12	1.515 (5)
C6—H6A	0.9900	C11—H11A	0.9900
C6—H6B	0.9900	C11—H11B	0.9900
C7—C15A	1.496 (9)	C12—H12A	0.9900
C7—C14	1.525 (6)	C12—H12B	0.9900
C7—C14A	1.549 (9)	C101—H10A	0.9800
C7—C8	1.583 (4)	C101—H10B	0.9800
C7—C15	1.586 (5)	C101—H10C	0.9800
C7—C6A	1.632 (8)	C311—H31A	0.9800
C14—H14A	0.9800	C311—H31B	0.9800
C14—H14B	0.9800	C311—H31C	0.9800
C14—H14C	0.9800

C2—C1—C12	116.7 (2)	C14—C7—C6A	67.3 (4)
C2—C1—C3	58.67 (19)	C14A—C7—C6A	103.5 (6)
C12—C1—C3	122.0 (2)	C8—C7—C6A	109.6 (4)
C2—C1—C8	118.1 (2)	C15—C7—C6A	144.0 (4)
C12—C1—C8	113.4 (2)	C7—C14—H14A	109.5
C3—C1—C8	117.3 (2)	C7—C14—H14B	109.5
C3—C2—C1	61.27 (19)	C7—C14—H14C	109.5
C3—C2—Br1	121.7 (2)	C7—C15—H15A	109.5
C1—C2—Br1	121.02 (19)	C7—C15—H15B	109.5
C3—C2—Br2	120.0 (2)	C7—C15—H15C	109.5
C1—C2—Br2	120.8 (2)	C7—C14A—H14D	109.5
Br1—C2—Br2	106.78 (14)	C7—C14A—H14E	109.5
C2—C3—C4	119.2 (3)	H14D—C14A—H14E	109.5
C2—C3—C311	118.7 (3)	C7—C14A—H14F	109.5
C4—C3—C311	112.5 (3)	H14D—C14A—H14F	109.5
C2—C3—C1	60.06 (19)	H14E—C14A—H14F	109.5
C4—C3—C1	118.7 (2)	C7—C15A—H15D	109.5
C311—C3—C1	118.4 (3)	C7—C15A—H15E	109.5
C3—C4—C5	113.7 (3)	H15D—C15A—H15E	109.5
C3—C4—H4A	108.8	C7—C15A—H15F	109.5
C5—C4—H4A	108.8	H15D—C15A—H15F	109.5
C3—C4—H4B	108.8	H15E—C15A—H15F	109.5
C5—C4—H4B	108.8	C5—C6A—C7	116.6 (6)
H4A—C4—H4B	107.7	C5—C6A—H6A1	108.1
C6A—C5—C4	116.0 (4)	C7—C6A—H6A1	108.1
C6A—C5—C6	53.5 (5)	C5—C6A—H6A2	108.1
C4—C5—C6	110.9 (3)	C7—C6A—H6A2	108.1
C6A—C5—H5A	57.4	H6A1—C6A—H6A2	107.3
C4—C5—H5A	109.5	C9—C8—C1	110.3 (2)
C6—C5—H5A	109.5	C9—C8—C7	112.7 (2)
C6A—C5—H5B	134.6	C1—C8—C7	115.7 (2)
C4—C5—H5B	109.5	C9—C8—H8	105.8
C6—C5—H5B	109.5	C1—C8—H8	105.8
H5A—C5—H5B	108.1	C7—C8—H8	105.8
C6A—C5—H5C	108.3	O1—C9—C10	120.3 (3)
C4—C5—H5C	108.3	O1—C9—C8	120.1 (3)
C6—C5—H5C	59.4	C10—C9—C8	119.6 (2)
H5A—C5—H5C	142.0	C101—C10—C9	112.3 (3)
H5B—C5—H5C	54.1	C101—C10—C11	113.0 (3)
C6A—C5—H5D	108.3	C9—C10—C11	109.3 (2)
C4—C5—H5D	108.3	C101—C10—H10	107.3
C6—C5—H5D	140.8	C9—C10—H10	107.3
H5A—C5—H5D	56.1	C11—C10—H10	107.3
H5B—C5—H5D	55.3	C12—C11—C10	112.5 (3)
H5C—C5—H5D	107.4	C12—C11—H11A	109.1
C7—C6—C5	117.4 (4)	C10—C11—H11A	109.1
C7—C6—H6A	107.9	C12—C11—H11B	109.1
C5—C6—H6A	107.9	C10—C11—H11B	109.1
C7—C6—H6B	107.9	H11A—C11—H11B	107.8
C5—C6—H6B	107.9	C11—C12—C1	109.9 (2)
H6A—C6—H6B	107.2	C11—C12—H12A	109.7
C6—C7—C15A	131.7 (5)	C1—C12—H12A	109.7
C6—C7—C14	113.1 (4)	C11—C12—H12B	109.7
C15A—C7—C14	40.1 (5)	C1—C12—H12B	109.7
C6—C7—C14A	53.5 (5)	H12A—C12—H12B	108.2
C15A—C7—C14A	111.7 (7)	C10—C101—H10A	109.5
C14—C7—C14A	135.3 (5)	C10—C101—H10B	109.5
C6—C7—C8	109.7 (3)	H10A—C101—H10B	109.5
C15A—C7—C8	118.2 (4)	C10—C101—H10C	109.5
C14—C7—C8	115.3 (3)	H10A—C101—H10C	109.5
C14A—C7—C8	109.0 (4)	H10B—C101—H10C	109.5
C6—C7—C15	106.8 (3)	C3—C311—H31A	109.5
C15A—C7—C15	66.7 (6)	C3—C311—H31B	109.5
C14—C7—C15	106.1 (4)	H31A—C311—H31B	109.5
C14A—C7—C15	55.0 (5)	C3—C311—H31C	109.5
C8—C7—C15	105.1 (3)	H31A—C311—H31C	109.5
C6—C7—C6A	52.2 (4)	H31B—C311—H31C	109.5
C15A—C7—C6A	103.7 (6)

Experimental details

Crystal data
Chemical formula	C₁₆H₂₄Br₂O
M_r	392.17
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	180
a, b, c (Å)	6.5975 (2), 15.2612 (3), 8.2688 (2)
β (°)	100.045 (3)
V (Å³)	819.79 (4)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	6.19
Crystal size (mm)	0.5 × 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	0.269, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6201, 2416, 2399
R_int	0.021
θ_max (°)	60.5
(sin θ/λ)_max (Å⁻¹)	0.565

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.057, 1.07
No. of reflections	2416
No. of parameters	206
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.46
Absolute structure	Flack & Bernardinelli (2000), 1127 Friedel pairs
Absolute structure parameter	0.01 (2)

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
El Haib, A., Benharref, A., Parres-Maynadié, S., Manoury, E., Urrutigoïty, M. & Gouygou, M. (2011). Tetrahedron Asymmetry, 22, 101–108. Web of Science CrossRef 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
Oukhrib, A., Benharref, A., Saadi, M., Berraho, M. & El Ammari, L. (2013). Acta Cryst. E69, o521–o522. CSD CrossRef CAS IUCr Journals Google Scholar
Ourhriss, N., Benharref, A., Saadi, M., El Ammari, L. & Berraho, M. (2013). Acta Cryst. E69, o275. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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