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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Daoubi, M., Duran-Patron, R., Hmamouchi, M., Hernandez-Galan, R., Benharref, A. & Isidro, G. C. (2004). Pest Manag. Sci. 60, 927-932.]); Benharref et al. (2013[Benharref, A., El Karroumi, J., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o1037-o1038.]); Oukhrib et al. (2013[Oukhrib, A., Benharref, A., Saadi, M., Berraho, M. & El Ammari, L. (2013). Acta Cryst. E69, o521-o522.]). For conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H26Br2

  • Mr = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.423, Tmax = 0.617

  • 11862 measured reflections

  • 5595 independent reflections

  • 4255 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.57 e Å−3

  • Δρmin = −0.34 e Å−3

  • Absolute structure: Flack & Bernardinelli (2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]), 614 Friedel pairs

  • Absolute structure parameter: 0.019 (12)

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


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.

Refinement top

All H atoms were fixed geometrically and treated as riding with C—H = 0.96 Å (methyl), 0.97 Å (methylene) and 0.98 Å (methine) with Uiso(H) = 1.2Ueq(methylene, methine) or Uiso(H) = 1.5Ueq(methyl).

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
[Figure 1] 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[6.5.0.01,3.09,11]tridecane top
Crystal data top
C17H26Br2F(000) = 792
Mr = 390.20Dx = 1.539 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5595 reflections
a = 6.585 (7) Åθ = 2.3–26.4°
b = 29.05 (3) ŵ = 4.80 mm1
c = 9.385 (9) ÅT = 296 K
β = 110.29 (2)°Box, colourless
V = 1684 (3) Å30.20 × 0.15 × 0.12 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
5595 independent reflections
Radiation source: fine-focus sealed tube4255 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω and ϕ scansθmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 88
Tmin = 0.423, Tmax = 0.617k = 3628
11862 measured reflectionsl = 1111
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0325P)2 + 0.0388P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
5595 reflectionsΔρmax = 0.57 e Å3
352 parametersΔρmin = 0.34 e Å3
1 restraintAbsolute structure: Flack & Bernardinelli (2000), 614 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.019 (12)
Crystal data top
C17H26Br2V = 1684 (3) Å3
Mr = 390.20Z = 4
Monoclinic, P21Mo Kα radiation
a = 6.585 (7) ŵ = 4.80 mm1
b = 29.05 (3) ÅT = 296 K
c = 9.385 (9) Å0.20 × 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)
Tmin = 0.423, Tmax = 0.617Rint = 0.041
11862 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.095Δρmax = 0.57 e Å3
S = 1.10Δρmin = 0.34 e Å3
5595 reflectionsAbsolute structure: Flack & Bernardinelli (2000), 614 Friedel pairs
352 parametersAbsolute 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
xyzUiso*/Ueq
C10.4761 (9)0.1497 (2)0.2261 (6)0.0368 (14)
C20.6203 (13)0.1079 (3)0.1740 (8)0.062 (2)
H2A0.77570.11280.13460.074*
H2B0.56950.08320.12530.074*
C30.5052 (12)0.1153 (2)0.3396 (7)0.0525 (17)
C40.6364 (13)0.1306 (3)0.4324 (10)0.074 (3)
H4A0.67410.10400.48040.088*
H4B0.76990.14440.36580.088*
C50.5191 (13)0.1650 (3)0.5532 (8)0.067 (2)
H5A0.62550.18260.58030.081*
H5B0.43150.14830.64300.081*
C60.3757 (13)0.1980 (3)0.5084 (8)0.061 (2)
H6A0.25860.18020.49520.074*
H6B0.31130.21860.59330.074*
C70.4736 (10)0.2272 (2)0.3674 (7)0.0436 (16)
C80.5756 (9)0.1969 (2)0.2176 (6)0.0302 (13)
H80.72860.19230.20400.036*
C90.5691 (9)0.2249 (2)0.0811 (6)0.0323 (13)
H90.56740.25810.10070.039*
C100.6687 (10)0.2146 (2)0.0815 (7)0.0403 (15)
C110.4226 (10)0.2126 (2)0.0055 (8)0.0428 (16)
C120.3200 (10)0.1654 (3)0.0218 (8)0.0513 (18)
H12A0.18670.16600.00030.062*
H12B0.41710.14340.04630.062*
C130.2710 (9)0.1499 (2)0.1868 (7)0.0467 (17)
H13A0.20900.11920.20050.056*
H13B0.16580.17050.25480.056*
C140.2810 (12)0.2499 (3)0.0397 (9)0.070 (2)
H14A0.14140.25020.03920.104*
H14B0.34880.27940.04420.104*
H14C0.26440.24350.13530.104*
C150.2804 (12)0.2568 (3)0.3617 (8)0.070 (2)
H15A0.21470.27210.45740.106*
H15B0.33140.27930.28230.106*
H15C0.17560.23720.34190.106*
C160.6498 (15)0.2587 (3)0.3829 (10)0.085 (3)
H16A0.75770.24060.40420.128*
H16B0.71540.27540.28980.128*
H16C0.58710.28010.46440.128*
C170.3222 (14)0.0823 (3)0.4235 (9)0.075 (2)
H17A0.21410.09850.50340.113*
H17B0.25860.07000.35370.113*
H17C0.37920.05750.46610.113*
C180.9410 (9)0.4778 (2)0.0423 (6)0.0364 (14)
C190.8677 (11)0.5225 (2)0.0944 (8)0.0507 (17)
H19A0.75070.52070.13470.061*
H19B0.97790.54520.14310.061*
C301.1803 (10)0.4724 (3)0.0799 (8)0.0533 (18)
H30A1.24280.50150.06640.064*
H30B1.20770.45010.01170.064*
C291.2851 (10)0.4563 (3)0.2431 (8)0.059 (2)
H29A1.43860.45160.26400.071*
H29B1.26980.48020.31070.071*
C281.1879 (9)0.4121 (3)0.2764 (8)0.0481 (17)
C271.0195 (9)0.4153 (2)0.3516 (7)0.0426 (15)
C260.9492 (8)0.4037 (2)0.1862 (6)0.0341 (13)
H260.91680.37090.16760.041*
C250.8217 (8)0.4331 (2)0.0498 (6)0.0325 (13)
H250.68550.44160.06330.039*
C240.7622 (10)0.4018 (2)0.0963 (7)0.0425 (16)
C230.7287 (12)0.4304 (3)0.2444 (8)0.059 (2)
H23A0.86520.44520.23380.071*
H23B0.69800.40890.32830.071*
C220.5528 (13)0.4673 (3)0.2892 (8)0.073 (2)
H22A0.41260.45260.31410.088*
H22B0.55620.48290.37970.088*
C210.5771 (12)0.5033 (3)0.1642 (9)0.067 (2)
H21A0.50230.53120.21030.080*
H21B0.50850.49180.09510.080*
C200.8121 (12)0.5148 (3)0.0742 (8)0.0542 (18)
C310.9226 (16)0.5428 (3)0.1623 (9)0.083 (3)
H31A0.84820.57160.19210.124*
H31B0.91950.52610.25120.124*
H31C1.07010.54850.09950.124*
C320.5532 (11)0.3758 (3)0.1142 (9)0.062 (2)
H32A0.51540.35670.20310.093*
H32B0.43880.39740.12450.093*
H32C0.57390.35690.02630.093*
C330.9350 (11)0.3668 (3)0.0930 (8)0.065 (2)
H33A0.95010.34500.01330.097*
H33B1.07040.38240.07480.097*
H33C0.89390.35110.18880.097*
C341.3466 (12)0.3709 (4)0.3125 (9)0.077 (3)
H34A1.41200.36870.23590.115*
H34B1.26910.34310.31420.115*
H34C1.45710.37550.40990.115*
Br10.79397 (12)0.26543 (3)0.21731 (8)0.0588 (2)
Br20.83916 (11)0.16088 (2)0.16108 (7)0.0514 (2)
Br30.94881 (11)0.47197 (3)0.42705 (8)0.0555 (2)
Br40.99939 (14)0.36640 (3)0.48505 (9)0.0678 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.039 (3)0.041 (4)0.028 (3)0.004 (3)0.008 (3)0.002 (3)
C20.093 (6)0.036 (4)0.048 (5)0.018 (4)0.014 (4)0.005 (3)
C30.079 (5)0.039 (4)0.036 (4)0.001 (4)0.015 (4)0.009 (3)
C40.078 (6)0.078 (7)0.067 (6)0.000 (5)0.026 (5)0.036 (5)
C50.095 (6)0.083 (6)0.031 (4)0.018 (5)0.032 (4)0.008 (4)
C60.079 (5)0.069 (6)0.031 (4)0.011 (4)0.013 (4)0.004 (4)
C70.048 (4)0.048 (4)0.030 (4)0.006 (3)0.006 (3)0.004 (3)
C80.025 (3)0.042 (4)0.023 (3)0.003 (2)0.008 (3)0.002 (3)
C90.035 (3)0.030 (3)0.027 (3)0.005 (2)0.003 (3)0.005 (3)
C100.045 (4)0.043 (4)0.033 (4)0.001 (3)0.014 (3)0.004 (3)
C110.041 (4)0.046 (4)0.045 (4)0.009 (3)0.020 (3)0.001 (3)
C120.038 (3)0.070 (5)0.053 (4)0.012 (3)0.025 (3)0.005 (4)
C130.040 (3)0.049 (4)0.051 (4)0.013 (3)0.015 (3)0.004 (3)
C140.069 (5)0.077 (6)0.066 (6)0.015 (4)0.027 (4)0.026 (4)
C150.088 (6)0.062 (6)0.043 (5)0.026 (4)0.002 (4)0.011 (4)
C160.123 (7)0.069 (6)0.069 (6)0.039 (5)0.039 (6)0.014 (5)
C170.110 (7)0.052 (5)0.058 (5)0.022 (5)0.022 (5)0.024 (4)
C180.040 (3)0.034 (4)0.031 (3)0.010 (3)0.007 (3)0.004 (3)
C190.064 (4)0.041 (4)0.041 (4)0.003 (3)0.010 (3)0.007 (3)
C300.054 (4)0.058 (4)0.055 (5)0.020 (4)0.029 (4)0.007 (4)
C290.031 (4)0.084 (6)0.058 (5)0.010 (3)0.011 (4)0.017 (4)
C280.032 (3)0.058 (5)0.045 (4)0.011 (3)0.002 (3)0.001 (3)
C270.038 (3)0.052 (4)0.034 (4)0.002 (3)0.008 (3)0.004 (3)
C260.031 (3)0.037 (4)0.029 (4)0.002 (2)0.004 (3)0.002 (3)
C250.025 (3)0.040 (4)0.030 (4)0.001 (2)0.006 (3)0.001 (3)
C240.047 (4)0.050 (4)0.026 (4)0.010 (3)0.006 (3)0.007 (3)
C230.071 (5)0.070 (6)0.030 (4)0.013 (4)0.010 (4)0.010 (4)
C220.077 (6)0.085 (7)0.041 (5)0.006 (5)0.000 (4)0.016 (5)
C210.058 (5)0.083 (6)0.051 (5)0.014 (4)0.009 (4)0.032 (5)
C200.068 (5)0.045 (5)0.051 (5)0.011 (4)0.023 (4)0.003 (3)
C310.123 (8)0.061 (6)0.063 (6)0.013 (5)0.030 (6)0.015 (5)
C320.048 (4)0.063 (6)0.064 (5)0.023 (4)0.005 (4)0.008 (4)
C330.072 (5)0.065 (5)0.061 (5)0.002 (4)0.027 (4)0.020 (4)
C340.062 (5)0.104 (7)0.061 (5)0.048 (5)0.015 (4)0.018 (5)
Br10.0718 (5)0.0608 (5)0.0380 (4)0.0117 (4)0.0117 (4)0.0143 (4)
Br20.0515 (4)0.0618 (5)0.0357 (4)0.0123 (3)0.0083 (3)0.0071 (3)
Br30.0632 (4)0.0594 (5)0.0394 (4)0.0123 (4)0.0121 (3)0.0079 (4)
Br40.0893 (5)0.0676 (6)0.0441 (5)0.0164 (4)0.0202 (4)0.0179 (4)
Geometric parameters (Å, º) top
C1—C81.510 (8)C18—C301.499 (9)
C1—C21.516 (9)C18—C191.522 (9)
C1—C131.519 (8)C18—C251.533 (8)
C1—C31.520 (8)C18—C201.559 (10)
C2—C31.490 (10)C19—C201.512 (10)
C2—H2A0.9700C19—H19A0.9700
C2—H2B0.9700C19—H19B0.9700
C3—C41.492 (10)C30—C291.519 (10)
C3—C171.528 (10)C30—H30A0.9700
C4—C51.507 (12)C30—H30B0.9700
C4—H4A0.9700C29—C281.515 (10)
C4—H4B0.9700C29—H29A0.9700
C5—C61.504 (11)C29—H29B0.9700
C5—H5A0.9700C28—C271.510 (8)
C5—H5B0.9700C28—C261.524 (8)
C6—C71.516 (10)C28—C341.545 (10)
C6—H6A0.9700C27—C261.496 (8)
C6—H6B0.9700C27—Br31.913 (7)
C7—C161.524 (9)C27—Br41.927 (7)
C7—C151.551 (10)C26—C251.524 (8)
C7—C81.596 (9)C26—H260.9800
C8—C91.531 (8)C25—C241.578 (8)
C8—H80.9800C25—H250.9800
C9—C101.468 (9)C24—C331.517 (10)
C9—C111.505 (8)C24—C321.527 (9)
C9—H90.9800C24—C231.568 (10)
C10—C111.529 (9)C23—C221.528 (11)
C10—Br21.917 (6)C23—H23A0.9700
C10—Br11.938 (7)C23—H23B0.9700
C11—C121.512 (10)C22—C211.538 (12)
C11—C141.534 (9)C22—H22A0.9700
C12—C131.536 (9)C22—H22B0.9700
C12—H12A0.9700C21—C201.521 (11)
C12—H12B0.9700C21—H21A0.9700
C13—H13A0.9700C21—H21B0.9700
C13—H13B0.9700C20—C311.513 (10)
C14—H14A0.9600C31—H31A0.9600
C14—H14B0.9600C31—H31B0.9600
C14—H14C0.9600C31—H31C0.9600
C15—H15A0.9600C32—H32A0.9600
C15—H15B0.9600C32—H32B0.9600
C15—H15C0.9600C32—H32C0.9600
C16—H16A0.9600C33—H33A0.9600
C16—H16B0.9600C33—H33B0.9600
C16—H16C0.9600C33—H33C0.9600
C17—H17A0.9600C34—H34A0.9600
C17—H17B0.9600C34—H34B0.9600
C17—H17C0.9600C34—H34C0.9600
C8—C1—C2120.0 (5)C30—C18—C19116.0 (5)
C8—C1—C13113.0 (5)C30—C18—C25114.4 (6)
C2—C1—C13115.8 (6)C19—C18—C25118.9 (5)
C8—C1—C3118.5 (5)C30—C18—C20120.7 (5)
C2—C1—C358.8 (4)C19—C18—C2058.8 (4)
C13—C1—C3120.7 (5)C25—C18—C20117.1 (5)
C3—C2—C160.8 (4)C20—C19—C1861.8 (4)
C3—C2—H2A117.7C20—C19—H19A117.6
C1—C2—H2A117.7C18—C19—H19A117.6
C3—C2—H2B117.7C20—C19—H19B117.6
C1—C2—H2B117.7C18—C19—H19B117.6
H2A—C2—H2B114.8H19A—C19—H19B114.7
C2—C3—C4117.6 (7)C18—C30—C29110.1 (5)
C2—C3—C160.5 (4)C18—C30—H30A109.6
C4—C3—C1116.8 (6)C29—C30—H30A109.6
C2—C3—C17118.2 (7)C18—C30—H30B109.6
C4—C3—C17113.5 (6)C29—C30—H30B109.6
C1—C3—C17120.4 (6)H30A—C30—H30B108.2
C3—C4—C5112.8 (7)C28—C29—C30113.1 (6)
C3—C4—H4A109.0C28—C29—H29A109.0
C5—C4—H4A109.0C30—C29—H29A109.0
C3—C4—H4B109.0C28—C29—H29B109.0
C5—C4—H4B109.0C30—C29—H29B109.0
H4A—C4—H4B107.8H29A—C29—H29B107.8
C6—C5—C4114.8 (5)C27—C28—C29118.4 (6)
C6—C5—H5A108.6C27—C28—C2659.1 (4)
C4—C5—H5A108.6C29—C28—C26116.6 (6)
C6—C5—H5B108.6C27—C28—C34119.7 (6)
C4—C5—H5B108.6C29—C28—C34113.5 (6)
H5A—C5—H5B107.6C26—C28—C34119.2 (7)
C5—C6—C7118.9 (7)C26—C27—C2860.9 (4)
C5—C6—H6A107.6C26—C27—Br3123.3 (5)
C7—C6—H6A107.6C28—C27—Br3122.6 (5)
C5—C6—H6B107.6C26—C27—Br4116.3 (5)
C7—C6—H6B107.6C28—C27—Br4119.0 (5)
H6A—C6—H6B107.0Br3—C27—Br4108.3 (3)
C6—C7—C16111.2 (6)C27—C26—C25128.9 (5)
C6—C7—C15103.6 (6)C27—C26—C2860.0 (4)
C16—C7—C15109.4 (7)C25—C26—C28122.7 (5)
C6—C7—C8112.4 (6)C27—C26—H26111.8
C16—C7—C8108.3 (6)C25—C26—H26111.8
C15—C7—C8112.0 (5)C28—C26—H26111.8
C1—C8—C9113.0 (4)C26—C25—C18111.8 (5)
C1—C8—C7114.3 (5)C26—C25—C24107.8 (5)
C9—C8—C7108.6 (5)C18—C25—C24115.2 (4)
C1—C8—H8106.8C26—C25—H25107.2
C9—C8—H8106.8C18—C25—H25107.2
C7—C8—H8106.8C24—C25—H25107.2
C10—C9—C1161.9 (4)C33—C24—C32108.2 (6)
C10—C9—C8129.0 (5)C33—C24—C23104.3 (5)
C11—C9—C8122.3 (5)C32—C24—C23108.7 (6)
C10—C9—H9111.6C33—C24—C25114.2 (5)
C11—C9—H9111.6C32—C24—C25108.8 (5)
C8—C9—H9111.6C23—C24—C25112.4 (6)
C9—C10—C1160.2 (4)C22—C23—C24118.5 (6)
C9—C10—Br2124.2 (4)C22—C23—H23A107.7
C11—C10—Br2122.3 (4)C24—C23—H23A107.7
C9—C10—Br1117.6 (4)C22—C23—H23B107.7
C11—C10—Br1118.5 (4)C24—C23—H23B107.7
Br2—C10—Br1107.8 (3)H23A—C23—H23B107.1
C9—C11—C12117.2 (5)C23—C22—C21113.5 (6)
C9—C11—C1057.9 (4)C23—C22—H22A108.9
C12—C11—C10116.9 (5)C21—C22—H22A108.9
C9—C11—C14119.7 (6)C23—C22—H22B108.9
C12—C11—C14114.1 (5)C21—C22—H22B108.9
C10—C11—C14119.9 (6)H22A—C22—H22B107.7
C11—C12—C13111.3 (5)C20—C21—C22112.9 (6)
C11—C12—H12A109.4C20—C21—H21A109.0
C13—C12—H12A109.4C22—C21—H21A109.0
C11—C12—H12B109.4C20—C21—H21B109.0
C13—C12—H12B109.4C22—C21—H21B109.0
H12A—C12—H12B108.0H21A—C21—H21B107.8
C1—C13—C12110.6 (5)C19—C20—C31120.4 (7)
C1—C13—H13A109.5C19—C20—C21116.3 (6)
C12—C13—H13A109.5C31—C20—C21113.9 (7)
C1—C13—H13B109.5C19—C20—C1859.4 (4)
C12—C13—H13B109.5C31—C20—C18120.4 (6)
H13A—C13—H13B108.1C21—C20—C18116.0 (6)
C11—C14—H14A109.5C20—C31—H31A109.5
C11—C14—H14B109.5C20—C31—H31B109.5
H14A—C14—H14B109.5H31A—C31—H31B109.5
C11—C14—H14C109.5C20—C31—H31C109.5
H14A—C14—H14C109.5H31A—C31—H31C109.5
H14B—C14—H14C109.5H31B—C31—H31C109.5
C7—C15—H15A109.5C24—C32—H32A109.5
C7—C15—H15B109.5C24—C32—H32B109.5
H15A—C15—H15B109.5H32A—C32—H32B109.5
C7—C15—H15C109.5C24—C32—H32C109.5
H15A—C15—H15C109.5H32A—C32—H32C109.5
H15B—C15—H15C109.5H32B—C32—H32C109.5
C7—C16—H16A109.5C24—C33—H33A109.5
C7—C16—H16B109.5C24—C33—H33B109.5
H16A—C16—H16B109.5H33A—C33—H33B109.5
C7—C16—H16C109.5C24—C33—H33C109.5
H16A—C16—H16C109.5H33A—C33—H33C109.5
H16B—C16—H16C109.5H33B—C33—H33C109.5
C3—C17—H17A109.5C28—C34—H34A109.5
C3—C17—H17B109.5C28—C34—H34B109.5
H17A—C17—H17B109.5H34A—C34—H34B109.5
C3—C17—H17C109.5C28—C34—H34C109.5
H17A—C17—H17C109.5H34A—C34—H34C109.5
H17B—C17—H17C109.5H34B—C34—H34C109.5

Experimental details

Crystal data
Chemical formulaC17H26Br2
Mr390.20
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)6.585 (7), 29.05 (3), 9.385 (9)
β (°) 110.29 (2)
V3)1684 (3)
Z4
Radiation typeMo Kα
µ (mm1)4.80
Crystal size (mm)0.20 × 0.15 × 0.12
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.423, 0.617
No. of measured, independent and
observed [I > 2σ(I)] reflections
11862, 5595, 4255
Rint0.041
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.095, 1.10
No. of reflections5595
No. of parameters352
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.57, 0.34
Absolute structureFlack & Bernardinelli (2000), 614 Friedel pairs
Absolute structure parameter0.019 (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

First citationBenharref, A., El Karroumi, J., El Ammari, L., Saadi, M. & Berraho, M. (2013). Acta Cryst. E69, o1037–o1038.  CSD CrossRef CAS IUCr Journals
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationDaoubi, 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
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationFlack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143–1148.  Web of Science CrossRef CAS IUCr Journals
First citationOukhrib, A., Benharref, A., Saadi, M., Berraho, M. & El Ammari, L. (2013). Acta Cryst. E69, o521–o522.  CSD CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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