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Acta Cryst. (2007). E63, o3681    [ doi:10.1107/S1600536807037403 ]

(1S,3R,6S)-3-Chloro-trans-himachalene

A. Benharref, N. Mazoir, B. Moha, L. Essediya and J.-C. Daran

Abstract top

The title compound, C15H25Cl, was semi-synthesized from natural essential oils of Cedrus atlantica. The stereochemistry has been confirmed by single-crystal X-ray diffraction. The asymmetric unit contains two chemically identical molecules. Each is built up from two fused six- and seven-membered rings. In both molecules, the six-membered ring has a perfect chair conformation, whereas the seven-membered ring displays a twist-chair conformation. In one molecule, the seven-membered ring is partially disordered with a site-occupancy ratio of 0.52:0.48.

Comment top

The isolated sesquiterpenes of Cedrus atlantica essential oils were the subject of hemisynthesis in order to prepare chlorinated sesquiterpenoid compounds (El Jamili et al., 2002; Dakir et al., 2004) in good yield. Indeed, these compounds were tested, using the food poisoning technique, for their potential antifungal activity against the phytopathogen Botrytis cinerea (Daoubi et al., 2005). Other molecules containing chlorine atom induces stalk-cell differentiation during development of Dictystelium discoideum (Kav et al., 1992).

We were interested in the study on the reactivity of compound (A) (Ourhriss et al., 2007) which has two chlorine atoms at different positions, 3 and 7 (Fig. 1). The dehydrohalogenation of (A) gave, after heating at reflux in methanol, the title compound (I) with high chemoselectivity. 1H and 13C NMR spectroscopy did not make it possible to identify the exact structure of this product. Single-crystal X-ray diffraction analysis allowed us to elucidate its configuration and to identify (I) as (1S,3R,6S)-3-chloro-trans-himachalene.

The molecule is built up from two fused six-membered and seven-membered rings (Fig. 2). The six membered ring has a perfect chair conformation as indicated by the total puckering amplitude QT= 0.560 (3) Å[0.546 (3) Å] and spherical polar angle θ=168.4 (3)° [174.1 (3)°] with φ= 117 (2)°[121 (3)°] whereas the seven-membered ring in the non disordered molecule displays a twist-chair conformation with QT= 0.807 (7) Å, θ= 36.7 (7)°, φ2= −179.8 (5)° and φ3= 120.8 (3)° (Cremer & Pople, 1975).

Owing to the presence of the Cl atom, the absolute configuration could be fully confirmed to be C1(S), C3(R) and C6(S) (Flack, 1983).

Related literature top

For general background see: El Jamili et al. (2002); Dakir et al. (2004); Daoubi et al. (2005); Kav et al. (1992). For a related structure see: Ourhriss et al. (2007). For related literature, see: Cremer & Pople (1975).

Experimental top

1 g (4.16 mmol) of compound (A) was dissolved in 15 ml of methanol. The mixture was heated until total dissolution, and then left resting at 0°C for 1 h. All this allowed us, after filtering under reduced pressure, to prepare (1S,3R,6S)-3-chloro-trans-himachalene, (I) in 84% yield. Suitable crystals were obtained by evaporation of a hexane solution at 277 K. m.p. = 325–326 K (hexane); Spectroscopic analysis: 1H NMR (300 MHz, CDCl3) δ (p.p.m.):1.63 (3H12, s), 4.65, 4.67 (Ha-13, Hb-13, 2 s), 0.80, 0.90 (3H14, 3H15, 2 s); 13C NMR (75 MHz, CDCl3) δ (p.p.m.): 47.9 (C-1), 43.0 (C-2), 72.0 (C-3), 42.9 (C-4), 24.4 (C-5), 43.3 (C-6), 155.9 (C-7), 41.5 (C-8), 32.9 (C-9), 31.7 (C-10) 43.4 (C-11), 34.7 (C-12), 110.5 (C-13), 30.2 (C-14), 22.3 (C-15).

Refinement top

All H atoms were fixed geometrically and treated as riding with C—H = 0.99 Å (CH2), 1.0 Å(CH) or 0.98 Å (CH3) with Uiso(H) = 1.2Ueq(CH, CH2) or Uiso(H) = 1.5Ueq(CH3).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Scheme showing the transformation of compound (A) to the title compound (I)
[Figure 2] Fig. 2. View of compound I with the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level, H atoms are represented as small spheres of arbitrary radii.
(1S,3R,6S)-3-Chloro-trans-himachalene top
Crystal data top
C15H25ClF000 = 1056
Mr = 240.80Dx = 1.134 Mg m−3
Orthorhombic, P212121Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3489 reflections
a = 6.0470 (2) Åθ = 2.7–32.1º
b = 15.7158 (7) ŵ = 0.25 mm−1
c = 29.6845 (12) ÅT = 180 (2) K
V = 2821.02 (19) Å3Prism, colourless
Z = 80.65 × 0.24 × 0.21 mm
Data collection top
Oxford Diffraction CCD Xcalibur
diffractometer		6222 independent reflections
Radiation source: fine-focus sealed tube3666 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
Detector resolution: 8.2632 pixels mm-1θmax = 27.1º
T = 180(2) Kθmin = 2.7º
ω and φ scansh = −7→5
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)		k = −20→20
Tmin = 0.756, Tmax = 1.000l = −38→38
23369 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044  w = 1/[σ2(Fo2) + (0.0662P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.132(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.41 e Å−3
6222 reflectionsΔρmin = −0.39 e Å−3
294 parametersExtinction correction: none
15 restraintsAbsolute structure: Flack (1983), based on 2652 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.11 (7)
Secondary atom site location: difference Fourier map
Crystal data top
C15H25ClV = 2821.02 (19) Å3
Mr = 240.80Z = 8
Orthorhombic, P212121Mo Kα
a = 6.0470 (2) ŵ = 0.25 mm−1
b = 15.7158 (7) ÅT = 180 (2) K
c = 29.6845 (12) Å0.65 × 0.24 × 0.21 mm
Data collection top
Oxford Diffraction CCD Xcalibur
diffractometer		6222 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)		3666 reflections with I > 2σ(I)
Tmin = 0.756, Tmax = 1.000Rint = 0.047
23369 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.132Δρmax = 0.41 e Å−3
S = 1.01Δρmin = −0.39 e Å−3
6222 reflectionsAbsolute structure: Flack (1983), based on 2652 Friedel pairs
294 parametersFlack parameter: −0.11 (7)
15 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl20.17012 (12)−0.00184 (5)0.82920 (3)0.0474 (2)
C10.5574 (5)0.12081 (18)0.87157 (9)0.0324 (7)
H10.40030.12200.88200.039*
C20.5564 (5)0.08395 (17)0.82356 (9)0.0340 (7)
H210.46690.12200.80420.041*
H220.70980.08520.81190.041*
C30.4693 (4)−0.00486 (19)0.81847 (10)0.0341 (7)
C40.5669 (5)−0.06490 (19)0.85311 (10)0.0394 (8)
H410.7214−0.07820.84460.047*
H420.4822−0.11880.85280.047*
C50.5647 (5)−0.02863 (17)0.90055 (10)0.0383 (8)
H510.6399−0.06860.92130.046*
H520.4099−0.02200.91080.046*
C60.6811 (5)0.05764 (18)0.90211 (9)0.0335 (7)
H60.83010.04900.88820.040*
C70.7212 (6)0.0838 (2)0.95016 (11)0.0456 (9)
C80.5674 (8)0.1440 (2)0.97280 (11)0.0621 (11)
H810.57930.13701.00590.075*
H820.41350.13060.96390.075*
C90.6195 (10)0.2348 (2)0.96037 (12)0.0794 (14)
H910.54660.27270.98250.095*
H920.78100.24340.96330.095*
C100.5521 (7)0.2611 (2)0.91505 (12)0.0606 (11)
H10A0.59040.32210.91190.073*
H10B0.38890.25710.91370.073*
C110.6439 (5)0.21461 (19)0.87306 (10)0.0369 (7)
C120.4969 (6)−0.0370 (2)0.77094 (10)0.0480 (9)
H12A0.41880.00100.75010.072*
H12B0.4353−0.09450.76860.072*
H12C0.6544−0.03830.76320.072*
C130.8968 (8)0.0533 (2)0.97185 (13)0.0701 (12)
H13A0.92480.07001.00210.084*
H13B0.99410.01480.95710.084*
C140.5492 (6)0.2663 (2)0.83362 (12)0.0525 (9)
H14A0.58890.32640.83730.079*
H14B0.38780.26070.83320.079*
H14C0.61040.24500.80520.079*
C150.8931 (5)0.2188 (2)0.87064 (13)0.0588 (10)
H15A0.94450.18780.84400.088*
H15B0.95650.19280.89770.088*
H15C0.94000.27830.86860.088*
Cl1A0.61711 (12)0.71053 (6)0.79807 (3)0.0478 (2)
C2A1.0131 (5)0.73751 (18)0.83943 (9)0.0317 (7)
H2A10.94270.79100.84960.038*
H2A21.17340.74870.83610.038*
C3A0.9197 (4)0.7146 (2)0.79321 (9)0.0367 (7)
C4A0.9978 (5)0.6273 (2)0.77819 (10)0.0448 (9)
H4A10.91570.61060.75070.054*
H4A21.15670.63050.77030.054*
C5A0.9659 (6)0.5603 (2)0.81364 (10)0.0464 (9)
H5A11.03020.50610.80290.056*
H5A20.80560.55130.81850.056*
C6A1.0739 (5)0.58486 (18)0.85846 (10)0.0371 (8)
H6A1.23560.59270.85280.044*
C7A1.0477 (6)0.5107 (2)0.89092 (12)0.0518 (9)
C8A0.8830 (13)0.5086 (7)0.9265 (2)0.0495 (10)0.52
H8A10.86510.44900.93670.059*0.52
H8A20.73960.52740.91380.059*0.52
C9A0.9364 (13)0.5634 (4)0.9670 (2)0.0495 (10)0.52
H9A10.83070.54910.99130.059*0.52
H9A21.08610.54810.97780.059*0.52
C10A0.9295 (12)0.6582 (4)0.9596 (2)0.0495 (10)0.52
H10C0.96980.68560.98850.059*0.52
H10D0.77370.67360.95340.059*0.52
C11A1.0726 (5)0.70010 (18)0.92240 (9)0.0325 (7)
C14A1.3124 (11)0.6824 (4)0.9264 (3)0.0462 (13)0.52
H14D1.39240.71340.90280.069*0.52
H14E1.33850.62120.92290.069*0.52
H14F1.36490.70100.95600.069*0.52
C15A1.0291 (11)0.7947 (5)0.9304 (3)0.0462 (13)0.52
H15D1.06880.80940.96140.069*0.52
H15E0.87200.80690.92540.069*0.52
H15F1.11850.82850.90950.069*0.52
C1A0.9818 (5)0.67051 (17)0.87616 (9)0.0287 (7)
H1A0.81870.66270.87990.034*
C8B0.8358 (14)0.5152 (7)0.9182 (3)0.0495 (10)0.48
H8B10.79780.45780.92960.059*0.48
H8B20.71320.53490.89870.059*0.48
C9B0.8644 (13)0.5785 (5)0.9593 (3)0.0495 (10)0.48
H9B10.73450.61680.95980.059*0.48
H9B20.86060.54450.98740.059*0.48
C10B1.0686 (13)0.6326 (4)0.9603 (2)0.0495 (10)0.48
H10E1.20020.59560.95740.059*0.48
H10F1.07760.66180.98980.059*0.48
C14B1.3206 (12)0.7264 (5)0.9206 (3)0.0462 (13)0.48
H14G1.37600.73490.95130.069*0.48
H14H1.33560.77950.90350.069*0.48
H14I1.40630.68150.90580.069*0.48
C15B0.9445 (12)0.7763 (5)0.9386 (3)0.0462 (13)0.48
H15G1.00120.79420.96810.069*0.48
H15H0.78770.76140.94140.069*0.48
H15I0.96110.82300.91700.069*0.48
C12A0.9693 (6)0.7850 (2)0.75919 (11)0.0520 (9)
H12D1.12930.78850.75430.078*
H12E0.91520.83950.77090.078*
H12F0.89530.77220.73060.078*
C13A1.1925 (9)0.4474 (2)0.88913 (15)0.0889 (16)
H13C1.18610.40280.91070.107*
H13D1.30260.44670.86630.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl20.0276 (4)0.0498 (5)0.0649 (5)−0.0004 (4)0.0030 (4)−0.0004 (4)
C10.0256 (16)0.0303 (16)0.0412 (17)0.0049 (14)0.0028 (14)0.0051 (14)
C20.0289 (16)0.0327 (16)0.0403 (17)0.0018 (14)0.0020 (14)0.0068 (14)
C30.0228 (14)0.0345 (16)0.0449 (17)0.0037 (15)0.0040 (13)0.0004 (15)
C40.0344 (18)0.0306 (16)0.0532 (19)0.0034 (15)0.0054 (16)−0.0015 (15)
C50.0431 (19)0.0285 (16)0.0432 (18)0.0067 (15)0.0044 (16)0.0083 (14)
C60.0263 (15)0.0369 (17)0.0372 (16)0.0071 (15)0.0050 (14)0.0029 (14)
C70.051 (2)0.0402 (19)0.046 (2)0.0000 (17)−0.0070 (18)0.0090 (16)
C80.094 (3)0.051 (2)0.041 (2)0.010 (2)0.013 (2)−0.0008 (17)
C90.127 (4)0.053 (2)0.059 (3)0.018 (3)0.013 (3)−0.005 (2)
C100.077 (3)0.0359 (19)0.068 (2)−0.003 (2)−0.007 (2)−0.0039 (18)
C110.0292 (16)0.0320 (16)0.0495 (18)0.0028 (15)0.0000 (15)0.0026 (15)
C120.051 (2)0.047 (2)0.0461 (19)0.0050 (18)0.0036 (18)−0.0039 (16)
C130.089 (3)0.060 (2)0.061 (2)0.010 (3)−0.026 (2)0.002 (2)
C140.056 (2)0.0362 (18)0.065 (2)−0.0034 (17)−0.003 (2)0.0113 (17)
C150.0369 (19)0.044 (2)0.096 (3)−0.0079 (18)−0.005 (2)0.011 (2)
Cl1A0.0273 (4)0.0734 (6)0.0428 (4)0.0024 (4)−0.0038 (4)−0.0059 (4)
C2A0.0239 (15)0.0372 (16)0.0340 (16)−0.0006 (13)0.0011 (13)−0.0088 (13)
C3A0.0222 (14)0.054 (2)0.0334 (16)−0.0012 (16)0.0013 (13)−0.0075 (16)
C4A0.0354 (18)0.062 (2)0.0371 (17)0.0020 (18)0.0024 (16)−0.0217 (17)
C5A0.044 (2)0.0458 (19)0.049 (2)−0.0010 (17)−0.0041 (16)−0.0180 (17)
C6A0.0301 (17)0.0368 (18)0.0442 (18)0.0043 (15)0.0017 (15)−0.0124 (15)
C7A0.062 (2)0.0309 (18)0.062 (2)0.0065 (19)−0.026 (2)−0.0100 (17)
C8A0.051 (3)0.056 (2)0.0415 (17)−0.005 (2)−0.0182 (18)0.0160 (15)
C9A0.051 (3)0.056 (2)0.0415 (17)−0.005 (2)−0.0182 (18)0.0160 (15)
C10A0.051 (3)0.056 (2)0.0415 (17)−0.005 (2)−0.0182 (18)0.0160 (15)
C11A0.0317 (16)0.0375 (17)0.0283 (15)0.0021 (15)−0.0019 (13)−0.0042 (13)
C14A0.037 (2)0.050 (3)0.051 (2)0.011 (3)−0.0151 (18)−0.023 (2)
C15A0.037 (2)0.050 (3)0.051 (2)0.011 (3)−0.0151 (18)−0.023 (2)
C1A0.0210 (14)0.0341 (16)0.0310 (15)0.0010 (13)0.0014 (13)−0.0045 (13)
C8B0.051 (3)0.056 (2)0.0415 (17)−0.005 (2)−0.0182 (18)0.0160 (15)
C9B0.051 (3)0.056 (2)0.0415 (17)−0.005 (2)−0.0182 (18)0.0160 (15)
C10B0.051 (3)0.056 (2)0.0415 (17)−0.005 (2)−0.0182 (18)0.0160 (15)
C14B0.037 (2)0.050 (3)0.051 (2)0.011 (3)−0.0151 (18)−0.023 (2)
C15B0.037 (2)0.050 (3)0.051 (2)0.011 (3)−0.0151 (18)−0.023 (2)
C12A0.044 (2)0.071 (2)0.0409 (19)0.000 (2)0.0039 (16)0.0043 (18)
C13A0.129 (4)0.050 (2)0.087 (3)0.035 (3)−0.033 (3)−0.014 (2)
Geometric parameters (Å, °) top
Cl2—C31.838 (3)C4A—H4A20.9900
C1—C21.538 (4)C5A—C6A1.531 (4)
C1—C61.538 (4)C5A—H5A10.9900
C1—C111.565 (4)C5A—H5A20.9900
C1—H11.0000C6A—C7A1.521 (4)
C2—C31.499 (4)C6A—C1A1.549 (4)
C2—H210.9900C6A—H6A1.0000
C2—H220.9900C7A—C13A1.326 (5)
C3—C121.508 (4)C7A—C8A1.451 (9)
C3—C41.515 (4)C7A—C8B1.518 (10)
C4—C51.519 (4)C8A—C9A1.515 (8)
C4—H410.9900C8A—H8A10.9900
C4—H420.9900C8A—H8A20.9900
C5—C61.528 (4)C9A—C10A1.507 (9)
C5—H510.9900C9A—H9A10.9900
C5—H520.9900C9A—H9A20.9900
C6—C71.504 (4)C10A—C11A1.549 (7)
C6—H61.0000C10A—H10C0.9900
C7—C131.331 (5)C10A—H10D0.9900
C7—C81.488 (5)C11A—C14A1.481 (7)
C8—C91.507 (5)C11A—C15B1.506 (8)
C8—H810.9900C11A—C15A1.528 (7)
C8—H820.9900C11A—C10B1.547 (6)
C9—C101.465 (5)C11A—C1A1.550 (4)
C9—H910.9900C11A—C14B1.557 (8)
C9—H920.9900C14A—H14D0.9800
C10—C111.548 (4)C14A—H14E0.9800
C10—H10A0.9900C14A—H14F0.9800
C10—H10B0.9900C15A—H15D0.9800
C11—C151.510 (4)C15A—H15E0.9800
C11—C141.536 (4)C15A—H15F0.9800
C12—H12A0.9800C1A—H1A1.0000
C12—H12B0.9800C8B—C9B1.583 (9)
C12—H12C0.9800C8B—H8B10.9900
C13—H13A0.9500C8B—H8B20.9900
C13—H13B0.9500C9B—C10B1.500 (10)
C14—H14A0.9800C9B—H9B10.9900
C14—H14B0.9800C9B—H9B20.9900
C14—H14C0.9800C10B—H10E0.9900
C15—H15A0.9800C10B—H10F0.9900
C15—H15B0.9800C14B—H14G0.9800
C15—H15C0.9800C14B—H14H0.9800
Cl1A—C3A1.837 (3)C14B—H14I0.9800
C2A—C3A1.527 (4)C15B—H15G0.9800
C2A—C1A1.528 (4)C15B—H15H0.9800
C2A—H2A10.9900C15B—H15I0.9800
C2A—H2A20.9900C12A—H12D0.9800
C3A—C4A1.518 (4)C12A—H12E0.9800
C3A—C12A1.527 (4)C12A—H12F0.9800
C4A—C5A1.501 (4)C13A—H13C0.9500
C4A—H4A10.9900C13A—H13D0.9500
C2—C1—C6107.8 (2)C4A—C5A—H5A2109.2
C2—C1—C11112.5 (2)C6A—C5A—H5A2109.2
C6—C1—C11115.4 (2)H5A1—C5A—H5A2107.9
C2—C1—H1106.9C7A—C6A—C5A108.3 (2)
C6—C1—H1106.9C7A—C6A—C1A114.4 (2)
C11—C1—H1106.9C5A—C6A—C1A111.1 (2)
C3—C2—C1116.4 (2)C7A—C6A—H6A107.6
C3—C2—H21108.2C5A—C6A—H6A107.6
C1—C2—H21108.2C1A—C6A—H6A107.6
C3—C2—H22108.2C13A—C7A—C8A117.7 (5)
C1—C2—H22108.2C13A—C7A—C8B127.9 (6)
H21—C2—H22107.3C8A—C7A—C8B14.9 (5)
C2—C3—C12111.5 (3)C13A—C7A—C6A118.8 (4)
C2—C3—C4112.0 (2)C8A—C7A—C6A123.3 (5)
C12—C3—C4112.5 (3)C8B—C7A—C6A113.0 (5)
C2—C3—Cl2107.7 (2)C7A—C8A—C9A114.8 (6)
C12—C3—Cl2106.2 (2)C7A—C8A—H8A1108.6
C4—C3—Cl2106.4 (2)C9A—C8A—H8A1108.6
C3—C4—C5113.1 (2)C7A—C8A—H8A2108.6
C3—C4—H41109.0C9A—C8A—H8A2108.6
C5—C4—H41109.0H8A1—C8A—H8A2107.6
C3—C4—H42109.0C10A—C9A—C8A116.1 (6)
C5—C4—H42109.0C10A—C9A—H9A1108.3
H41—C4—H42107.8C8A—C9A—H9A1108.3
C4—C5—C6110.9 (2)C10A—C9A—H9A2108.3
C4—C5—H51109.5C8A—C9A—H9A2108.3
C6—C5—H51109.5H9A1—C9A—H9A2107.4
C4—C5—H52109.5C9A—C10A—C11A120.6 (6)
C6—C5—H52109.5C9A—C10A—H10C107.2
H51—C5—H52108.0C11A—C10A—H10C107.2
C7—C6—C5110.2 (2)C9A—C10A—H10D107.2
C7—C6—C1117.5 (2)C11A—C10A—H10D107.2
C5—C6—C1109.3 (2)H10C—C10A—H10D106.8
C7—C6—H6106.4C14A—C11A—C15B128.8 (5)
C5—C6—H6106.4C14A—C11A—C15A109.8 (4)
C1—C6—H6106.4C15B—C11A—C15A24.2 (4)
C13—C7—C8120.6 (3)C14A—C11A—C10B80.1 (5)
C13—C7—C6119.3 (3)C15B—C11A—C10B107.7 (5)
C8—C7—C6120.1 (3)C15A—C11A—C10B123.4 (5)
C7—C8—C9111.2 (3)C14A—C11A—C10A114.2 (5)
C7—C8—H81109.4C15B—C11A—C10A79.8 (4)
C9—C8—H81109.4C15A—C11A—C10A101.9 (4)
C7—C8—H82109.4C10B—C11A—C10A35.1 (3)
C9—C8—H82109.4C14A—C11A—C1A111.2 (3)
H81—C8—H82108.0C15B—C11A—C1A109.9 (4)
C10—C9—C8115.7 (4)C15A—C11A—C1A111.6 (4)
C10—C9—H91108.4C10B—C11A—C1A115.7 (3)
C8—C9—H91108.4C10A—C11A—C1A107.8 (3)
C10—C9—H92108.4C14A—C11A—C14B27.0 (3)
C8—C9—H92108.4C15B—C11A—C14B107.2 (5)
H91—C9—H92107.4C15A—C11A—C14B85.0 (4)
C9—C10—C11120.4 (3)C10B—C11A—C14B102.9 (4)
C9—C10—H10A107.2C10A—C11A—C14B132.5 (5)
C11—C10—H10A107.2C1A—C11A—C14B113.0 (4)
C9—C10—H10B107.2C11A—C14A—H14D109.5
C11—C10—H10B107.2C11A—C14A—H14E109.5
H10A—C10—H10B106.9C11A—C14A—H14F109.5
C15—C11—C14108.2 (3)C11A—C15A—H15D109.5
C15—C11—C10112.1 (3)C11A—C15A—H15E109.5
C14—C11—C10103.3 (3)C11A—C15A—H15F109.5
C15—C11—C1111.9 (3)C2A—C1A—C6A108.2 (2)
C14—C11—C1110.6 (2)C2A—C1A—C11A112.4 (2)
C10—C11—C1110.3 (2)C6A—C1A—C11A115.7 (2)
C3—C12—H12A109.5C2A—C1A—H1A106.7
C3—C12—H12B109.5C6A—C1A—H1A106.7
H12A—C12—H12B109.5C11A—C1A—H1A106.7
C3—C12—H12C109.5C7A—C8B—C9B110.4 (6)
H12A—C12—H12C109.5C7A—C8B—H8B1109.6
H12B—C12—H12C109.5C9B—C8B—H8B1109.6
C7—C13—H13A120.0C7A—C8B—H8B2109.6
C7—C13—H13B120.0C9B—C8B—H8B2109.6
H13A—C13—H13B120.0H8B1—C8B—H8B2108.1
C11—C14—H14A109.5C10B—C9B—C8B117.5 (7)
C11—C14—H14B109.5C10B—C9B—H9B1107.9
H14A—C14—H14B109.5C8B—C9B—H9B1107.9
C11—C14—H14C109.5C10B—C9B—H9B2107.9
H14A—C14—H14C109.5C8B—C9B—H9B2107.9
H14B—C14—H14C109.5H9B1—C9B—H9B2107.2
C11—C15—H15A109.5C9B—C10B—C11A112.8 (5)
C11—C15—H15B109.5C9B—C10B—H10E109.0
H15A—C15—H15B109.5C11A—C10B—H10E109.0
C11—C15—H15C109.5C9B—C10B—H10F109.0
H15A—C15—H15C109.5C11A—C10B—H10F109.0
H15B—C15—H15C109.5H10E—C10B—H10F107.8
C3A—C2A—C1A115.7 (2)C11A—C14B—H14G109.5
C3A—C2A—H2A1108.4C11A—C14B—H14H109.5
C1A—C2A—H2A1108.4H14G—C14B—H14H109.5
C3A—C2A—H2A2108.4C11A—C14B—H14I109.5
C1A—C2A—H2A2108.4H14G—C14B—H14I109.5
H2A1—C2A—H2A2107.4H14H—C14B—H14I109.5
C4A—C3A—C2A111.2 (2)C11A—C15B—H15G109.5
C4A—C3A—C12A113.5 (2)C11A—C15B—H15H109.5
C2A—C3A—C12A110.6 (2)H15G—C15B—H15H109.5
C4A—C3A—Cl1A107.5 (2)C11A—C15B—H15I109.5
C2A—C3A—Cl1A107.83 (19)H15G—C15B—H15I109.5
C12A—C3A—Cl1A105.9 (2)H15H—C15B—H15I109.5
C5A—C4A—C3A112.8 (2)C3A—C12A—H12D109.5
C5A—C4A—H4A1109.0C3A—C12A—H12E109.5
C3A—C4A—H4A1109.0H12D—C12A—H12E109.5
C5A—C4A—H4A2109.0C3A—C12A—H12F109.5
C3A—C4A—H4A2109.0H12D—C12A—H12F109.5
H4A1—C4A—H4A2107.8H12E—C12A—H12F109.5
C4A—C5A—C6A112.2 (3)C7A—C13A—H13C120.0
C4A—C5A—H5A1109.2C7A—C13A—H13D120.0
C6A—C5A—H5A1109.2H13C—C13A—H13D120.0
Acknowledgements top

The authors are grateful to Professor A. Idmessaaoud for her invaluable help.

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