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

Benharref, A.; El karroumi, J.; El Ammari, L.; Saadi, M.; Berraho, M.

doi:10.1107/S160053681301903X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1261

doi:10.1107/S160053681301903X

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

Ahmed Benharref,^a Jamal El karroumi,^a ^* Lahcen El Ammari,^b Mohamed Saadi ^b and Moha Berraho ^a

^aLaboratoire de Chimie des Substances Naturelles, "Unité Associé au CNRST (URAC16)", Faculté des Sciences Semlalia, BP 2390 Bd My Abdellah, 40000 Marrakech, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université MohammedV-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: berraho@uca.ma

(Received 4 July 2013; accepted 9 July 2013; online 13 July 2013)

The title compound, C₁₇H₂₆Br₂, 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 appended three-membered rings. In both molecules, the six-membered ring has a screw boat conformation, whereas the seven-membered ring displays a boat conformation. No specific intermolecular interactions were discerned in the crystal packing.

Related literature

For backgroud to Moroccan floral heritage, see: Daoubi et al. (2004 ); Benharref et al. (2013 ); Oukhrib et al. (2013 ). For conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₇H₂₆Br₂
M_r = 390.20
Monoclinic, P 2₁
a = 6.585 (7) Å
b = 29.05 (3) Å
c = 9.385 (9) Å
β = 110.29 (2)°
V = 1684 (3) Å³
Z = 4
Mo Kα radiation
μ = 4.80 mm⁻¹
T = 296 K
0.20 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.423, T_max = 0.617
11862 measured reflections
5595 independent reflections
4255 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.095
S = 1.10
5595 reflections
352 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack & Bernardinelli (2000 ), 614 Friedel pairs
Absolute structure parameter: 0.019 (12)

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: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681301903X/tk5238sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681301903X/tk5238Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681301903X/tk5238Isup3.cml

checkCIF report

Comment top

As part of the development of our Moroccan floral heritage, we continue to study the reactivity of β-himachalene, constituting principal (50%) of the essential oil of the Atlas cedar (Cedrus Atlantica) (Oukhrib et al., 2013; Benharref et al., 2013), in order to prepare new products having biological properties (Daoubi et al., 2004). In this work we present the crystal structure of the title compound, (1S,3S,8R,9S,11R)-10,10-dibromo-3,7,7,11-tetramethyl- tetracyclo-[6.5.0.01,3.09,11]tridecane.

Each molecule contains a fused six-and seven-membered rings, which is fused to two three-membered rings as shown in Fig. 1. The six-membered ring has a screw boat conformation, as indicated by the total puckering amplitude QT = 0.492 (6) Å and spherical polar angle θ = 139.6 (7)° with ϕ = 130.8 (1)°, whereas the seven-membered ring display a boat conformation with QT = 1.1449 (8) Å, θ = 88.49 (5)°, ϕ2 = -49.77 (5)° and ϕ3 = -127.91 (13)° (Cremer & Pople, 1975). Owing to the presence of Br atoms, the absolute configuration could be fully confirmed, by refining the Flack parameter (Flack & Bernardinelli (2000)) as C1(S), C3(S), C8(R),C9(S)and C11(R).

Related literature top

For backgroud to Moroccan floral heritage, see: Daoubi et al. (2004); Benharref et al. (2013); Oukhrib et al. (2013). For conformational analysis, see: Cremer & Pople (1975).

Experimental top

A solution containing 2 g (9 mmol) of (1S,3S,8R,9S,11R)- 3,7,7,11-tetramethyltri-cyclo-[6.5.0.0¹,³]tridec-9-ene) (Benharref et al., 2013) and 1 ml (10 mmol) of CHBr₃ in 40 ml of dichloromethane was added drop-wise at 273 K over 30 min to 1 g of pulverized sodium hydroxide and 40 mg of N-benzyltriethylammonium chloride placed in a 100 ml three-necked flask. After stirring at room temperature for 2 h, the mixture was filtered on celite and impregnated with silver nitrate (10%) with a mixture of hexane-ethyl acetate (95:5 v/v) used as eluent. The two diastereoisomers (1S,3S,8R,9S,11R)-10,10-dibromo-3,7,7,11- tetramethyltetracyclo- [6.5.0.0¹,³.0⁹,¹¹]tridecane (X) and (1S,3S,8R,9R,11S)-10,10-dibromo-3,7,7,11- tetramethyltetracyclo-[6.5.0.0¹,³.0⁹,¹¹]tridecane (Y), were obtained by this procedure in a 85:15 ratio and a combined yield of 86% (3 g; 7.7 mmol). The title compound (isomer X) was recrystallized from n-heptane.

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. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability. level.

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

Crystal data top

C₁₇H₂₆Br₂	F(000) = 792
M_r = 390.20	D_x = 1.539 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5595 reflections
a = 6.585 (7) Å	θ = 2.3–26.4°
b = 29.05 (3) Å	µ = 4.80 mm⁻¹
c = 9.385 (9) Å	T = 296 K
β = 110.29 (2)°	Box, colourless
V = 1684 (3) Å³	0.20 × 0.15 × 0.12 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5595 independent reflections
Radiation source: fine-focus sealed tube	4255 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω and ϕ scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.423, T_max = 0.617	k = −36→28
11862 measured 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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0325P)² + 0.0388P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
5595 reflections	Δρ_max = 0.57 e Å⁻³
352 parameters	Δρ_min = −0.34 e Å⁻³
1 restraint	Absolute structure: Flack & Bernardinelli (2000), 614 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.019 (12)

Crystal data top

C₁₇H₂₆Br₂	V = 1684 (3) Å³
M_r = 390.20	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 6.585 (7) Å	µ = 4.80 mm⁻¹
b = 29.05 (3) Å	T = 296 K
c = 9.385 (9) Å	0.20 × 0.15 × 0.12 mm
β = 110.29 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5595 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4255 reflections with I > 2σ(I)
T_min = 0.423, T_max = 0.617	R_int = 0.041
11862 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.095	Δρ_max = 0.57 e Å⁻³
S = 1.10	Δρ_min = −0.34 e Å⁻³
5595 reflections	Absolute structure: Flack & Bernardinelli (2000), 614 Friedel pairs
352 parameters	Absolute structure parameter: 0.019 (12)
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	0.4761 (9)	0.1497 (2)	−0.2261 (6)	0.0368 (14)
C2	0.6203 (13)	0.1079 (3)	−0.1740 (8)	0.062 (2)
H2A	0.7757	0.1128	−0.1346	0.074*
H2B	0.5695	0.0832	−0.1253	0.074*
C3	0.5052 (12)	0.1153 (2)	−0.3396 (7)	0.0525 (17)
C4	0.6364 (13)	0.1306 (3)	−0.4324 (10)	0.074 (3)
H4A	0.6741	0.1040	−0.4804	0.088*
H4B	0.7699	0.1444	−0.3658	0.088*
C5	0.5191 (13)	0.1650 (3)	−0.5532 (8)	0.067 (2)
H5A	0.6255	0.1826	−0.5803	0.081*
H5B	0.4315	0.1483	−0.6430	0.081*
C6	0.3757 (13)	0.1980 (3)	−0.5084 (8)	0.061 (2)
H6A	0.2586	0.1802	−0.4952	0.074*
H6B	0.3113	0.2186	−0.5933	0.074*
C7	0.4736 (10)	0.2272 (2)	−0.3674 (7)	0.0436 (16)
C8	0.5756 (9)	0.1969 (2)	−0.2176 (6)	0.0302 (13)
H8	0.7286	0.1923	−0.2040	0.036*
C9	0.5691 (9)	0.2249 (2)	−0.0811 (6)	0.0323 (13)
H9	0.5674	0.2581	−0.1007	0.039*
C10	0.6687 (10)	0.2146 (2)	0.0815 (7)	0.0403 (15)
C11	0.4226 (10)	0.2126 (2)	0.0055 (8)	0.0428 (16)
C12	0.3200 (10)	0.1654 (3)	−0.0218 (8)	0.0513 (18)
H12A	0.1867	0.1660	0.0003	0.062*
H12B	0.4171	0.1434	0.0463	0.062*
C13	0.2710 (9)	0.1499 (2)	−0.1868 (7)	0.0467 (17)
H13A	0.2090	0.1192	−0.2005	0.056*
H13B	0.1658	0.1705	−0.2548	0.056*
C14	0.2810 (12)	0.2499 (3)	0.0397 (9)	0.070 (2)
H14A	0.1414	0.2502	−0.0392	0.104*
H14B	0.3488	0.2794	0.0442	0.104*
H14C	0.2644	0.2435	0.1353	0.104*
C15	0.2804 (12)	0.2568 (3)	−0.3617 (8)	0.070 (2)
H15A	0.2147	0.2721	−0.4574	0.106*
H15B	0.3314	0.2793	−0.2823	0.106*
H15C	0.1756	0.2372	−0.3419	0.106*
C16	0.6498 (15)	0.2587 (3)	−0.3829 (10)	0.085 (3)
H16A	0.7577	0.2406	−0.4042	0.128*
H16B	0.7154	0.2754	−0.2898	0.128*
H16C	0.5871	0.2801	−0.4644	0.128*
C17	0.3222 (14)	0.0823 (3)	−0.4235 (9)	0.075 (2)
H17A	0.2141	0.0985	−0.5034	0.113*
H17B	0.2586	0.0700	−0.3537	0.113*
H17C	0.3792	0.0575	−0.4661	0.113*
C18	0.9410 (9)	0.4778 (2)	0.0423 (6)	0.0364 (14)
C19	0.8677 (11)	0.5225 (2)	0.0944 (8)	0.0507 (17)
H19A	0.7507	0.5207	0.1347	0.061*
H19B	0.9779	0.5452	0.1431	0.061*
C30	1.1803 (10)	0.4724 (3)	0.0799 (8)	0.0533 (18)
H30A	1.2428	0.5015	0.0664	0.064*
H30B	1.2077	0.4501	0.0117	0.064*
C29	1.2851 (10)	0.4563 (3)	0.2431 (8)	0.059 (2)
H29A	1.4386	0.4516	0.2640	0.071*
H29B	1.2698	0.4802	0.3107	0.071*
C28	1.1879 (9)	0.4121 (3)	0.2764 (8)	0.0481 (17)
C27	1.0195 (9)	0.4153 (2)	0.3516 (7)	0.0426 (15)
C26	0.9492 (8)	0.4037 (2)	0.1862 (6)	0.0341 (13)
H26	0.9168	0.3709	0.1676	0.041*
C25	0.8217 (8)	0.4331 (2)	0.0498 (6)	0.0325 (13)
H25	0.6855	0.4416	0.0633	0.039*
C24	0.7622 (10)	0.4018 (2)	−0.0963 (7)	0.0425 (16)
C23	0.7287 (12)	0.4304 (3)	−0.2444 (8)	0.059 (2)
H23A	0.8652	0.4452	−0.2338	0.071*
H23B	0.6980	0.4089	−0.3283	0.071*
C22	0.5528 (13)	0.4673 (3)	−0.2892 (8)	0.073 (2)
H22A	0.4126	0.4526	−0.3141	0.088*
H22B	0.5562	0.4829	−0.3797	0.088*
C21	0.5771 (12)	0.5033 (3)	−0.1642 (9)	0.067 (2)
H21A	0.5023	0.5312	−0.2103	0.080*
H21B	0.5085	0.4918	−0.0951	0.080*
C20	0.8121 (12)	0.5148 (3)	−0.0742 (8)	0.0542 (18)
C31	0.9226 (16)	0.5428 (3)	−0.1623 (9)	0.083 (3)
H31A	0.8482	0.5716	−0.1921	0.124*
H31B	0.9195	0.5261	−0.2512	0.124*
H31C	1.0701	0.5485	−0.0995	0.124*
C32	0.5532 (11)	0.3758 (3)	−0.1142 (9)	0.062 (2)
H32A	0.5154	0.3567	−0.2031	0.093*
H32B	0.4388	0.3974	−0.1245	0.093*
H32C	0.5739	0.3569	−0.0263	0.093*
C33	0.9350 (11)	0.3668 (3)	−0.0930 (8)	0.065 (2)
H33A	0.9501	0.3450	−0.0133	0.097*
H33B	1.0704	0.3824	−0.0748	0.097*
H33C	0.8939	0.3511	−0.1888	0.097*
C34	1.3466 (12)	0.3709 (4)	0.3125 (9)	0.077 (3)
H34A	1.4120	0.3687	0.2359	0.115*
H34B	1.2691	0.3431	0.3142	0.115*
H34C	1.4571	0.3755	0.4099	0.115*
Br1	0.79397 (12)	0.26543 (3)	0.21731 (8)	0.0588 (2)
Br2	0.83916 (11)	0.16088 (2)	0.16108 (7)	0.0514 (2)
Br3	0.94881 (11)	0.47197 (3)	0.42705 (8)	0.0555 (2)
Br4	0.99939 (14)	0.36640 (3)	0.48505 (9)	0.0678 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.039 (3)	0.041 (4)	0.028 (3)	0.004 (3)	0.008 (3)	0.002 (3)
C2	0.093 (6)	0.036 (4)	0.048 (5)	0.018 (4)	0.014 (4)	−0.005 (3)
C3	0.079 (5)	0.039 (4)	0.036 (4)	0.001 (4)	0.015 (4)	−0.009 (3)
C4	0.078 (6)	0.078 (7)	0.067 (6)	0.000 (5)	0.026 (5)	−0.036 (5)
C5	0.095 (6)	0.083 (6)	0.031 (4)	−0.018 (5)	0.032 (4)	−0.008 (4)
C6	0.079 (5)	0.069 (6)	0.031 (4)	−0.011 (4)	0.013 (4)	0.004 (4)
C7	0.048 (4)	0.048 (4)	0.030 (4)	−0.006 (3)	0.006 (3)	0.004 (3)
C8	0.025 (3)	0.042 (4)	0.023 (3)	−0.003 (2)	0.008 (3)	0.002 (3)
C9	0.035 (3)	0.030 (3)	0.027 (3)	−0.005 (2)	0.003 (3)	0.005 (3)
C10	0.045 (4)	0.043 (4)	0.033 (4)	0.001 (3)	0.014 (3)	0.004 (3)
C11	0.041 (4)	0.046 (4)	0.045 (4)	0.009 (3)	0.020 (3)	0.001 (3)
C12	0.038 (3)	0.070 (5)	0.053 (4)	−0.012 (3)	0.025 (3)	0.005 (4)
C13	0.040 (3)	0.049 (4)	0.051 (4)	−0.013 (3)	0.015 (3)	−0.004 (3)
C14	0.069 (5)	0.077 (6)	0.066 (6)	0.015 (4)	0.027 (4)	−0.026 (4)
C15	0.088 (6)	0.062 (6)	0.043 (5)	0.026 (4)	−0.002 (4)	0.011 (4)
C16	0.123 (7)	0.069 (6)	0.069 (6)	−0.039 (5)	0.039 (6)	0.014 (5)
C17	0.110 (7)	0.052 (5)	0.058 (5)	−0.022 (5)	0.022 (5)	−0.024 (4)
C18	0.040 (3)	0.034 (4)	0.031 (3)	−0.010 (3)	0.007 (3)	−0.004 (3)
C19	0.064 (4)	0.041 (4)	0.041 (4)	−0.003 (3)	0.010 (3)	−0.007 (3)
C30	0.054 (4)	0.058 (4)	0.055 (5)	−0.020 (4)	0.029 (4)	−0.007 (4)
C29	0.031 (4)	0.084 (6)	0.058 (5)	−0.010 (3)	0.011 (4)	−0.017 (4)
C28	0.032 (3)	0.058 (5)	0.045 (4)	0.011 (3)	0.002 (3)	−0.001 (3)
C27	0.038 (3)	0.052 (4)	0.034 (4)	0.002 (3)	0.008 (3)	−0.004 (3)
C26	0.031 (3)	0.037 (4)	0.029 (4)	0.002 (2)	0.004 (3)	−0.002 (3)
C25	0.025 (3)	0.040 (4)	0.030 (4)	−0.001 (2)	0.006 (3)	0.001 (3)
C24	0.047 (4)	0.050 (4)	0.026 (4)	−0.010 (3)	0.006 (3)	−0.007 (3)
C23	0.071 (5)	0.070 (6)	0.030 (4)	−0.013 (4)	0.010 (4)	−0.010 (4)
C22	0.077 (6)	0.085 (7)	0.041 (5)	−0.006 (5)	0.000 (4)	0.016 (5)
C21	0.058 (5)	0.083 (6)	0.051 (5)	0.014 (4)	0.009 (4)	0.032 (5)
C20	0.068 (5)	0.045 (5)	0.051 (5)	−0.011 (4)	0.023 (4)	0.003 (3)
C31	0.123 (8)	0.061 (6)	0.063 (6)	−0.013 (5)	0.030 (6)	0.015 (5)
C32	0.048 (4)	0.063 (6)	0.064 (5)	−0.023 (4)	0.005 (4)	−0.008 (4)
C33	0.072 (5)	0.065 (5)	0.061 (5)	−0.002 (4)	0.027 (4)	−0.020 (4)
C34	0.062 (5)	0.104 (7)	0.061 (5)	0.048 (5)	0.015 (4)	0.018 (5)
Br1	0.0718 (5)	0.0608 (5)	0.0380 (4)	−0.0117 (4)	0.0117 (4)	−0.0143 (4)
Br2	0.0515 (4)	0.0618 (5)	0.0357 (4)	0.0123 (3)	0.0083 (3)	0.0071 (3)
Br3	0.0632 (4)	0.0594 (5)	0.0394 (4)	0.0123 (4)	0.0121 (3)	−0.0079 (4)
Br4	0.0893 (5)	0.0676 (6)	0.0441 (5)	0.0164 (4)	0.0202 (4)	0.0179 (4)

Geometric parameters (Å, º) top

C1—C8	1.510 (8)	C18—C30	1.499 (9)
C1—C2	1.516 (9)	C18—C19	1.522 (9)
C1—C13	1.519 (8)	C18—C25	1.533 (8)
C1—C3	1.520 (8)	C18—C20	1.559 (10)
C2—C3	1.490 (10)	C19—C20	1.512 (10)
C2—H2A	0.9700	C19—H19A	0.9700
C2—H2B	0.9700	C19—H19B	0.9700
C3—C4	1.492 (10)	C30—C29	1.519 (10)
C3—C17	1.528 (10)	C30—H30A	0.9700
C4—C5	1.507 (12)	C30—H30B	0.9700
C4—H4A	0.9700	C29—C28	1.515 (10)
C4—H4B	0.9700	C29—H29A	0.9700
C5—C6	1.504 (11)	C29—H29B	0.9700
C5—H5A	0.9700	C28—C27	1.510 (8)
C5—H5B	0.9700	C28—C26	1.524 (8)
C6—C7	1.516 (10)	C28—C34	1.545 (10)
C6—H6A	0.9700	C27—C26	1.496 (8)
C6—H6B	0.9700	C27—Br3	1.913 (7)
C7—C16	1.524 (9)	C27—Br4	1.927 (7)
C7—C15	1.551 (10)	C26—C25	1.524 (8)
C7—C8	1.596 (9)	C26—H26	0.9800
C8—C9	1.531 (8)	C25—C24	1.578 (8)
C8—H8	0.9800	C25—H25	0.9800
C9—C10	1.468 (9)	C24—C33	1.517 (10)
C9—C11	1.505 (8)	C24—C32	1.527 (9)
C9—H9	0.9800	C24—C23	1.568 (10)
C10—C11	1.529 (9)	C23—C22	1.528 (11)
C10—Br2	1.917 (6)	C23—H23A	0.9700
C10—Br1	1.938 (7)	C23—H23B	0.9700
C11—C12	1.512 (10)	C22—C21	1.538 (12)
C11—C14	1.534 (9)	C22—H22A	0.9700
C12—C13	1.536 (9)	C22—H22B	0.9700
C12—H12A	0.9700	C21—C20	1.521 (11)
C12—H12B	0.9700	C21—H21A	0.9700
C13—H13A	0.9700	C21—H21B	0.9700
C13—H13B	0.9700	C20—C31	1.513 (10)
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

C8—C1—C2	120.0 (5)	C30—C18—C19	116.0 (5)
C8—C1—C13	113.0 (5)	C30—C18—C25	114.4 (6)
C2—C1—C13	115.8 (6)	C19—C18—C25	118.9 (5)
C8—C1—C3	118.5 (5)	C30—C18—C20	120.7 (5)
C2—C1—C3	58.8 (4)	C19—C18—C20	58.8 (4)
C13—C1—C3	120.7 (5)	C25—C18—C20	117.1 (5)
C3—C2—C1	60.8 (4)	C20—C19—C18	61.8 (4)
C3—C2—H2A	117.7	C20—C19—H19A	117.6
C1—C2—H2A	117.7	C18—C19—H19A	117.6
C3—C2—H2B	117.7	C20—C19—H19B	117.6
C1—C2—H2B	117.7	C18—C19—H19B	117.6
H2A—C2—H2B	114.8	H19A—C19—H19B	114.7
C2—C3—C4	117.6 (7)	C18—C30—C29	110.1 (5)
C2—C3—C1	60.5 (4)	C18—C30—H30A	109.6
C4—C3—C1	116.8 (6)	C29—C30—H30A	109.6
C2—C3—C17	118.2 (7)	C18—C30—H30B	109.6
C4—C3—C17	113.5 (6)	C29—C30—H30B	109.6
C1—C3—C17	120.4 (6)	H30A—C30—H30B	108.2
C3—C4—C5	112.8 (7)	C28—C29—C30	113.1 (6)
C3—C4—H4A	109.0	C28—C29—H29A	109.0
C5—C4—H4A	109.0	C30—C29—H29A	109.0
C3—C4—H4B	109.0	C28—C29—H29B	109.0
C5—C4—H4B	109.0	C30—C29—H29B	109.0
H4A—C4—H4B	107.8	H29A—C29—H29B	107.8
C6—C5—C4	114.8 (5)	C27—C28—C29	118.4 (6)
C6—C5—H5A	108.6	C27—C28—C26	59.1 (4)
C4—C5—H5A	108.6	C29—C28—C26	116.6 (6)
C6—C5—H5B	108.6	C27—C28—C34	119.7 (6)
C4—C5—H5B	108.6	C29—C28—C34	113.5 (6)
H5A—C5—H5B	107.6	C26—C28—C34	119.2 (7)
C5—C6—C7	118.9 (7)	C26—C27—C28	60.9 (4)
C5—C6—H6A	107.6	C26—C27—Br3	123.3 (5)
C7—C6—H6A	107.6	C28—C27—Br3	122.6 (5)
C5—C6—H6B	107.6	C26—C27—Br4	116.3 (5)
C7—C6—H6B	107.6	C28—C27—Br4	119.0 (5)
H6A—C6—H6B	107.0	Br3—C27—Br4	108.3 (3)
C6—C7—C16	111.2 (6)	C27—C26—C25	128.9 (5)
C6—C7—C15	103.6 (6)	C27—C26—C28	60.0 (4)
C16—C7—C15	109.4 (7)	C25—C26—C28	122.7 (5)
C6—C7—C8	112.4 (6)	C27—C26—H26	111.8
C16—C7—C8	108.3 (6)	C25—C26—H26	111.8
C15—C7—C8	112.0 (5)	C28—C26—H26	111.8
C1—C8—C9	113.0 (4)	C26—C25—C18	111.8 (5)
C1—C8—C7	114.3 (5)	C26—C25—C24	107.8 (5)
C9—C8—C7	108.6 (5)	C18—C25—C24	115.2 (4)
C1—C8—H8	106.8	C26—C25—H25	107.2
C9—C8—H8	106.8	C18—C25—H25	107.2
C7—C8—H8	106.8	C24—C25—H25	107.2
C10—C9—C11	61.9 (4)	C33—C24—C32	108.2 (6)
C10—C9—C8	129.0 (5)	C33—C24—C23	104.3 (5)
C11—C9—C8	122.3 (5)	C32—C24—C23	108.7 (6)
C10—C9—H9	111.6	C33—C24—C25	114.2 (5)
C11—C9—H9	111.6	C32—C24—C25	108.8 (5)
C8—C9—H9	111.6	C23—C24—C25	112.4 (6)
C9—C10—C11	60.2 (4)	C22—C23—C24	118.5 (6)
C9—C10—Br2	124.2 (4)	C22—C23—H23A	107.7
C11—C10—Br2	122.3 (4)	C24—C23—H23A	107.7
C9—C10—Br1	117.6 (4)	C22—C23—H23B	107.7
C11—C10—Br1	118.5 (4)	C24—C23—H23B	107.7
Br2—C10—Br1	107.8 (3)	H23A—C23—H23B	107.1
C9—C11—C12	117.2 (5)	C23—C22—C21	113.5 (6)
C9—C11—C10	57.9 (4)	C23—C22—H22A	108.9
C12—C11—C10	116.9 (5)	C21—C22—H22A	108.9
C9—C11—C14	119.7 (6)	C23—C22—H22B	108.9
C12—C11—C14	114.1 (5)	C21—C22—H22B	108.9
C10—C11—C14	119.9 (6)	H22A—C22—H22B	107.7
C11—C12—C13	111.3 (5)	C20—C21—C22	112.9 (6)
C11—C12—H12A	109.4	C20—C21—H21A	109.0
C13—C12—H12A	109.4	C22—C21—H21A	109.0
C11—C12—H12B	109.4	C20—C21—H21B	109.0
C13—C12—H12B	109.4	C22—C21—H21B	109.0
H12A—C12—H12B	108.0	H21A—C21—H21B	107.8
C1—C13—C12	110.6 (5)	C19—C20—C31	120.4 (7)
C1—C13—H13A	109.5	C19—C20—C21	116.3 (6)
C12—C13—H13A	109.5	C31—C20—C21	113.9 (7)
C1—C13—H13B	109.5	C19—C20—C18	59.4 (4)
C12—C13—H13B	109.5	C31—C20—C18	120.4 (6)
H13A—C13—H13B	108.1	C21—C20—C18	116.0 (6)
C11—C14—H14A	109.5	C20—C31—H31A	109.5
C11—C14—H14B	109.5	C20—C31—H31B	109.5
H14A—C14—H14B	109.5	H31A—C31—H31B	109.5
C11—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
C3—C17—H17A	109.5	C28—C34—H34A	109.5
C3—C17—H17B	109.5	C28—C34—H34B	109.5
H17A—C17—H17B	109.5	H34A—C34—H34B	109.5
C3—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	C₁₇H₂₆Br₂
M_r	390.20
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	6.585 (7), 29.05 (3), 9.385 (9)
β (°)	110.29 (2)
V (Å³)	1684 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.80
Crystal size (mm)	0.20 × 0.15 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.423, 0.617
No. of measured, independent and observed [I > 2σ(I)] reflections	11862, 5595, 4255
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.095, 1.10
No. of reflections	5595
No. of parameters	352
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.34
Absolute structure	Flack & Bernardinelli (2000), 614 Friedel pairs
Absolute structure parameter	0.019 (12)

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Benharref, A., El Karroumi, J., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o1037–o1038. CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Daoubi, M., Duran-Patron, R., Hmamouchi, M., Hernandez-Galan, R., Benharref, A. & Isidro, G. C. (2004). Pest Manag. Sci. 60, 927–932. Web of Science CrossRef PubMed 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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