(1R,4R,6S,7R)-5,5-Di-bromo-1,4,8,8-tetra-methyl-tri-cyclo-[5.4.1.0(4,6)]dodecan-12-one.

The title compound, C16H24Br2O, was synthesized from the reaction of β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from Atlas cedar (Cedrus atlantica). The asymmetric unit contains two independent mol-ecules with similar conformations. Each mol-ecule is built up from two fused seven-membered rings and an additional three-membered ring. In both mol-ecules, one of the seven-membered rings has a chair conformation, whereas the other displays a screw-boat conformation.

Related literature

For background to β-himachalene, see: El Haib et al. (2011 ▶). For the reactivity of this sesquiterpene and its derivatives, see: El Jamili et al. (2002 ▶); Benharref et al. (2013 ▶); Oukhrib et al. (2013 ▶). For their potential anti­fungal activity against the phytopathogen Botrytis cinerea, see: Daoubi et al. (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H24Br2O

M = 392.17

Triclinic,

a = 6.6550 (3) Å

b = 9.4142 (4) Å

c = 12.9389 (13) Å

α = 86.008 (6)°

β = 83.921 (6)°

γ = 89.511 (4)°

V = 804.13 (9) Å3

Z = 2

Mo Kα radiation

μ = 5.03 mm−1

T = 173 K

0.38 × 0.11 × 0.10 mm

Data collection

Agilent Xcalibur (Eos, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.670, T max = 1.00

11451 measured reflections

6327 independent reflections

5209 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.119

S = 1.01

6327 reflections

351 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −0.62 e Å−3

Absolute structure: Flack & Bernardinelli (2000 ▶), 3035 Friedel pairs

Absolute structure parameter: −0.017 (15)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814007351/bt6972sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007351/bt6972Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007351/bt6972Isup3.cml

CCDC reference: 995040

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H24Br2O	Z = 2
Mr = 392.17	F(000) = 396
Triclinic, P1	Dx = 1.620 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6550 (3) Å	Cell parameters from 2828 reflections
b = 9.4142 (4) Å	θ = 3.7–26.6°
c = 12.9389 (13) Å	µ = 5.03 mm−1
α = 86.008 (6)°	T = 173 K
β = 83.921 (6)°	Needle, colourless
γ = 89.511 (4)°	0.38 × 0.11 × 0.10 mm
V = 804.13 (9) Å3

Agilent Xcalibur (Eos, Gemini ultra) diffractometer	6327 independent reflections
Radiation source: fine-focus sealed tube	5209 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 16.1978 pixels mm-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −11→11
Tmin = 0.670, Tmax = 1.00	l = −16→16
11451 measured reflections

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0447P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
6327 reflections	Δρmax = 0.77 e Å−3
351 parameters	Δρmin = −0.62 e Å−3
3 restraints	Absolute structure: Flack & Bernardinelli (2000), 3035 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.017 (15)

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 > σ(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.

	x	y	z	Uiso*/Ueq
C1	0.5880 (12)	−0.1550 (8)	1.2375 (6)	0.0276 (18)
C2	0.5505 (13)	−0.0914 (9)	1.3464 (6)	0.034 (2)
H2A	0.4417	−0.1471	1.3886	0.040*
H2B	0.6748	−0.1053	1.3818	0.040*
C3	0.4926 (12)	0.0666 (9)	1.3462 (7)	0.028 (2)
H3A	0.4717	0.0941	1.4191	0.034*
H3B	0.6059	0.1241	1.3098	0.034*
C4	0.3007 (11)	0.1013 (8)	1.2934 (6)	0.0252 (18)
C5	0.2942 (11)	0.2374 (8)	1.2238 (6)	0.0225 (17)
C6	0.3148 (11)	0.0978 (7)	1.1734 (6)	0.0191 (17)
H6	0.1873	0.0660	1.1475	0.023*
C7	0.5057 (11)	0.0591 (8)	1.1050 (6)	0.0226 (17)
H7	0.5764	0.1510	1.0817	0.027*
C8	0.4504 (11)	−0.0078 (8)	1.0021 (6)	0.0275 (18)
C9	0.3174 (14)	−0.1435 (8)	1.0270 (7)	0.033 (2)
H9A	0.1841	−0.1137	1.0599	0.039*
H9B	0.2948	−0.1823	0.9600	0.039*
C10	0.3944 (13)	−0.2635 (8)	1.0963 (7)	0.032 (2)
H10A	0.5336	−0.2882	1.0683	0.039*
H10B	0.3086	−0.3484	1.0942	0.039*
C11	0.3955 (12)	−0.2268 (8)	1.2106 (6)	0.0281 (19)
H11A	0.2794	−0.1633	1.2280	0.034*
H11B	0.3738	−0.3158	1.2557	0.034*
C12	0.6585 (11)	−0.0347 (8)	1.1572 (6)	0.0221 (17)
C13	0.7592 (14)	−0.2668 (10)	1.2418 (8)	0.039 (2)
H13A	0.7752	−0.3149	1.1767	0.059*
H13B	0.7249	−0.3370	1.3004	0.059*
H13C	0.8859	−0.2193	1.2510	0.059*
C14	0.6448 (14)	−0.0429 (10)	0.9350 (6)	0.037 (2)
H14A	0.6112	−0.0806	0.8703	0.056*
H14B	0.7220	−0.1143	0.9732	0.056*
H14C	0.7259	0.0437	0.9186	0.056*
C15	0.3312 (14)	0.1068 (9)	0.9411 (6)	0.031 (2)
H15A	0.3025	0.0710	0.8748	0.046*
H15B	0.4121	0.1939	0.9274	0.046*
H15C	0.2038	0.1277	0.9825	0.046*
C16	0.1080 (12)	0.0472 (9)	1.3566 (7)	0.037 (2)
H16A	0.0519	0.1213	1.4010	0.055*
H16B	0.1382	−0.0379	1.4004	0.055*
H16C	0.0094	0.0233	1.3094	0.055*
O1	0.8370 (8)	−0.0058 (6)	1.1385 (5)	0.0370 (15)
Br1	0.51009 (11)	0.37150 (8)	1.21049 (7)	0.0329 (3)
Br2	0.04085 (11)	0.33708 (9)	1.21682 (7)	0.0376 (3)
C1A	0.2236 (11)	0.6190 (8)	0.6230 (6)	0.0250 (17)
C2A	0.2439 (12)	0.5548 (8)	0.5146 (6)	0.0284 (19)
H2C	0.1584	0.6115	0.4690	0.034*
H2D	0.3858	0.5664	0.4836	0.034*
C3A	0.1869 (11)	0.3985 (9)	0.5135 (7)	0.024 (2)
H3C	0.2845	0.3398	0.5505	0.029*
H3D	0.1994	0.3720	0.4403	0.029*
C4A	−0.0271 (11)	0.3624 (8)	0.5636 (6)	0.0237 (17)
C5A	−0.0676 (11)	0.2274 (8)	0.6295 (6)	0.0208 (17)
C6A	−0.0769 (11)	0.3672 (7)	0.6818 (6)	0.0193 (16)
H6A1	−0.2177	0.3998	0.7029	0.023*
C7A	0.0724 (11)	0.4048 (7)	0.7548 (6)	0.0208 (16)
H7A1	0.1292	0.3125	0.7819	0.025*
C8A	−0.0317 (11)	0.4772 (7)	0.8529 (5)	0.0233 (17)
C9A	−0.1548 (13)	0.6092 (8)	0.8239 (6)	0.027 (2)
H9A1	−0.2120	0.6492	0.8895	0.032*
H9A2	−0.2699	0.5776	0.7887	0.032*
C10A	−0.0473 (13)	0.7314 (8)	0.7539 (6)	0.034 (2)
H10C	−0.1388	0.8148	0.7518	0.040*
H10D	0.0745	0.7597	0.7852	0.040*
C11A	0.0146 (11)	0.6919 (8)	0.6438 (6)	0.0258 (18)
H11C	0.0137	0.7796	0.5969	0.031*
H11D	−0.0896	0.6275	0.6240	0.031*
C12A	0.2523 (11)	0.4925 (7)	0.7042 (6)	0.0237 (17)
C13A	0.3950 (13)	0.7266 (9)	0.6268 (7)	0.035 (2)
H13D	0.3753	0.8098	0.5791	0.053*
H13E	0.5252	0.6818	0.6059	0.053*
H13F	0.3939	0.7566	0.6979	0.053*
C14A	−0.1763 (13)	0.3701 (8)	0.9151 (7)	0.032 (2)
H14D	−0.2433	0.4139	0.9761	0.049*
H14E	−0.1004	0.2861	0.9378	0.049*
H14F	−0.2782	0.3416	0.8711	0.049*
C15A	0.1302 (13)	0.5154 (8)	0.9242 (6)	0.0308 (19)
H15D	0.2236	0.5859	0.8868	0.046*
H15E	0.2053	0.4294	0.9437	0.046*
H15F	0.0639	0.5550	0.9871	0.046*
C16A	−0.1904 (12)	0.4126 (9)	0.4946 (7)	0.036 (2)
H16D	−0.1881	0.3525	0.4356	0.054*
H16E	−0.1646	0.5117	0.4687	0.054*
H16F	−0.3231	0.4056	0.5354	0.054*
O2	0.4216 (8)	0.4614 (6)	0.7244 (5)	0.0338 (14)
Br3	0.14860 (10)	0.09484 (7)	0.65374 (6)	0.0290 (2)
Br4	−0.31319 (12)	0.12276 (9)	0.62628 (7)	0.0378 (3)

	U11	U22	U33	U12	U13	U23
C1	0.029 (5)	0.015 (4)	0.039 (5)	0.006 (3)	−0.006 (4)	−0.002 (3)
C2	0.032 (5)	0.042 (5)	0.027 (5)	0.003 (4)	−0.011 (4)	0.003 (4)
C3	0.028 (5)	0.038 (6)	0.021 (5)	0.002 (4)	−0.012 (4)	−0.006 (4)
C4	0.020 (4)	0.028 (4)	0.027 (4)	0.000 (3)	−0.003 (3)	0.005 (3)
C5	0.014 (4)	0.030 (4)	0.022 (4)	0.011 (3)	0.002 (3)	−0.002 (3)
C6	0.018 (4)	0.019 (4)	0.022 (4)	0.002 (3)	−0.008 (3)	−0.001 (3)
C7	0.020 (4)	0.021 (4)	0.025 (4)	0.005 (3)	0.004 (3)	−0.003 (3)
C8	0.030 (5)	0.027 (4)	0.025 (5)	0.008 (3)	0.002 (4)	−0.002 (3)
C9	0.029 (5)	0.030 (5)	0.042 (6)	−0.008 (4)	−0.015 (4)	−0.007 (4)
C10	0.036 (5)	0.021 (4)	0.041 (5)	0.005 (3)	−0.013 (4)	−0.004 (4)
C11	0.030 (4)	0.023 (5)	0.031 (5)	0.000 (3)	−0.004 (4)	0.004 (4)
C12	0.019 (4)	0.021 (4)	0.027 (4)	0.001 (3)	−0.003 (3)	−0.009 (3)
C13	0.040 (6)	0.037 (5)	0.043 (6)	0.006 (4)	−0.018 (5)	0.006 (4)
C14	0.048 (6)	0.046 (6)	0.018 (5)	0.012 (4)	0.003 (4)	−0.007 (4)
C15	0.044 (6)	0.034 (5)	0.017 (4)	0.015 (4)	−0.012 (4)	−0.009 (4)
C16	0.024 (5)	0.050 (6)	0.034 (5)	−0.008 (4)	0.007 (4)	−0.003 (4)
O1	0.017 (3)	0.034 (3)	0.059 (4)	0.005 (2)	−0.001 (3)	0.000 (3)
Br1	0.0291 (5)	0.0234 (5)	0.0468 (6)	0.0026 (3)	−0.0041 (4)	−0.0068 (4)
Br2	0.0272 (5)	0.0480 (6)	0.0380 (6)	0.0191 (4)	−0.0027 (4)	−0.0084 (5)
C1A	0.017 (4)	0.031 (4)	0.024 (4)	0.000 (3)	0.005 (3)	0.000 (3)
C2A	0.028 (4)	0.028 (4)	0.026 (5)	0.006 (3)	0.010 (4)	0.001 (3)
C3A	0.020 (4)	0.024 (5)	0.027 (5)	0.001 (3)	0.005 (4)	−0.003 (4)
C4A	0.015 (4)	0.022 (4)	0.035 (5)	0.000 (3)	−0.004 (3)	0.000 (3)
C5A	0.018 (4)	0.029 (4)	0.016 (4)	−0.002 (3)	−0.001 (3)	−0.006 (3)
C6A	0.018 (4)	0.014 (4)	0.024 (4)	0.005 (3)	0.004 (3)	0.002 (3)
C7A	0.024 (4)	0.016 (4)	0.023 (4)	0.004 (3)	−0.003 (3)	−0.006 (3)
C8A	0.034 (5)	0.023 (4)	0.013 (4)	0.003 (3)	−0.003 (3)	−0.002 (3)
C9A	0.021 (4)	0.030 (4)	0.027 (5)	0.008 (3)	0.011 (4)	−0.004 (4)
C10A	0.038 (5)	0.017 (4)	0.043 (5)	0.013 (3)	0.009 (4)	0.001 (4)
C11A	0.024 (4)	0.012 (4)	0.039 (5)	0.004 (3)	0.002 (4)	0.003 (3)
C12A	0.021 (4)	0.018 (4)	0.031 (5)	0.004 (3)	0.002 (3)	−0.006 (3)
C13A	0.034 (5)	0.026 (5)	0.045 (6)	−0.004 (4)	0.003 (4)	−0.001 (4)
C14A	0.029 (5)	0.024 (4)	0.041 (5)	0.005 (4)	0.006 (4)	0.004 (4)
C15A	0.045 (5)	0.024 (4)	0.025 (5)	0.003 (4)	−0.010 (4)	−0.005 (3)
C16A	0.027 (5)	0.051 (6)	0.030 (5)	0.002 (4)	−0.006 (4)	−0.003 (4)
O2	0.016 (3)	0.035 (3)	0.050 (4)	0.001 (2)	−0.003 (3)	−0.001 (3)
Br3	0.0281 (5)	0.0210 (5)	0.0387 (6)	0.0047 (3)	−0.0057 (4)	−0.0052 (4)
Br4	0.0263 (5)	0.0444 (6)	0.0443 (6)	−0.0121 (4)	−0.0082 (4)	−0.0074 (5)

C1—C12	1.525 (11)	C1A—C13A	1.539 (11)
C1—C11	1.537 (11)	C1A—C11A	1.552 (10)
C1—C13	1.547 (11)	C1A—C12A	1.557 (10)
C1—C2	1.564 (11)	C1A—C2A	1.557 (11)
C2—C3	1.534 (12)	C2A—C3A	1.524 (11)
C2—H2A	0.9900	C2A—H2C	0.9900
C2—H2B	0.9900	C2A—H2D	0.9900
C3—C4	1.534 (10)	C3A—C4A	1.532 (9)
C3—H3A	0.9900	C3A—H3C	0.9900
C3—H3B	0.9900	C3A—H3D	0.9900
C4—C5	1.517 (10)	C4A—C5A	1.490 (10)
C4—C16	1.519 (10)	C4A—C16A	1.529 (11)
C4—C6	1.548 (10)	C4A—C6A	1.534 (10)
C5—C6	1.506 (11)	C5A—C6A	1.518 (10)
C5—Br1	1.907 (8)	C5A—Br4	1.921 (7)
C5—Br2	1.930 (7)	C5A—Br3	1.933 (8)
C6—C7	1.527 (9)	C6A—C7A	1.503 (10)
C6—H6	1.0000	C6A—H6A1	1.0000
C7—C12	1.522 (10)	C7A—C12A	1.523 (10)
C7—C8	1.591 (10)	C7A—C8A	1.575 (10)
C7—H7	1.0000	C7A—H7A1	1.0000
C8—C14	1.526 (10)	C8A—C14A	1.526 (10)
C8—C15	1.555 (10)	C8A—C9A	1.530 (10)
C8—C9	1.556 (11)	C8A—C15A	1.551 (10)
C9—C10	1.513 (11)	C9A—C10A	1.545 (11)
C9—H9A	0.9900	C9A—H9A1	0.9900
C9—H9B	0.9900	C9A—H9A2	0.9900
C10—C11	1.542 (11)	C10A—C11A	1.512 (11)
C10—H10A	0.9900	C10A—H10C	0.9900
C10—H10B	0.9900	C10A—H10D	0.9900
C11—H11A	0.9900	C11A—H11C	0.9900
C11—H11B	0.9900	C11A—H11D	0.9900
C12—O1	1.217 (9)	C12A—O2	1.212 (9)
C13—H13A	0.9800	C13A—H13D	0.9800
C13—H13B	0.9800	C13A—H13E	0.9800
C13—H13C	0.9800	C13A—H13F	0.9800
C14—H14A	0.9800	C14A—H14D	0.9800
C14—H14B	0.9800	C14A—H14E	0.9800
C14—H14C	0.9800	C14A—H14F	0.9800
C15—H15A	0.9800	C15A—H15D	0.9800
C15—H15B	0.9800	C15A—H15E	0.9800
C15—H15C	0.9800	C15A—H15F	0.9800
C16—H16A	0.9800	C16A—H16D	0.9800
C16—H16B	0.9800	C16A—H16E	0.9800
C16—H16C	0.9800	C16A—H16F	0.9800
C12—C1—C11	111.9 (7)	C13A—C1A—C11A	110.5 (7)
C12—C1—C13	108.5 (7)	C13A—C1A—C12A	108.2 (7)
C11—C1—C13	109.4 (6)	C11A—C1A—C12A	112.0 (6)
C12—C1—C2	108.1 (6)	C13A—C1A—C2A	109.6 (6)
C11—C1—C2	110.6 (7)	C11A—C1A—C2A	110.4 (7)
C13—C1—C2	108.3 (7)	C12A—C1A—C2A	106.0 (6)
C3—C2—C1	116.4 (7)	C3A—C2A—C1A	116.6 (6)
C3—C2—H2A	108.2	C3A—C2A—H2C	108.2
C1—C2—H2A	108.2	C1A—C2A—H2C	108.2
C3—C2—H2B	108.2	C3A—C2A—H2D	108.2
C1—C2—H2B	108.2	C1A—C2A—H2D	108.2
H2A—C2—H2B	107.3	H2C—C2A—H2D	107.3
C4—C3—C2	113.0 (7)	C2A—C3A—C4A	114.3 (6)
C4—C3—H3A	109.0	C2A—C3A—H3C	108.7
C2—C3—H3A	109.0	C4A—C3A—H3C	108.7
C4—C3—H3B	109.0	C2A—C3A—H3D	108.7
C2—C3—H3B	109.0	C4A—C3A—H3D	108.7
H3A—C3—H3B	107.8	H3C—C3A—H3D	107.6
C5—C4—C16	119.2 (7)	C5A—C4A—C16A	116.7 (6)
C5—C4—C3	118.8 (6)	C5A—C4A—C3A	120.5 (6)
C16—C4—C3	113.7 (7)	C16A—C4A—C3A	112.8 (7)
C5—C4—C6	58.9 (5)	C5A—C4A—C6A	60.2 (5)
C16—C4—C6	118.0 (7)	C16A—C4A—C6A	117.5 (7)
C3—C4—C6	117.7 (7)	C3A—C4A—C6A	119.6 (6)
C6—C5—C4	61.6 (5)	C4A—C5A—C6A	61.3 (5)
C6—C5—Br1	121.7 (5)	C4A—C5A—Br4	121.0 (5)
C4—C5—Br1	121.1 (5)	C6A—C5A—Br4	118.9 (5)
C6—C5—Br2	116.7 (6)	C4A—C5A—Br3	120.7 (5)
C4—C5—Br2	119.3 (5)	C6A—C5A—Br3	119.2 (5)
Br1—C5—Br2	109.6 (4)	Br4—C5A—Br3	109.0 (3)
C5—C6—C7	121.8 (7)	C7A—C6A—C5A	122.4 (6)
C5—C6—C4	59.5 (5)	C7A—C6A—C4A	124.3 (6)
C7—C6—C4	124.2 (6)	C5A—C6A—C4A	58.5 (5)
C5—C6—H6	113.6	C7A—C6A—H6A1	113.6
C7—C6—H6	113.6	C5A—C6A—H6A1	113.6
C4—C6—H6	113.6	C4A—C6A—H6A1	113.6
C12—C7—C6	116.5 (6)	C6A—C7A—C12A	114.9 (6)
C12—C7—C8	110.2 (6)	C6A—C7A—C8A	112.2 (6)
C6—C7—C8	110.8 (6)	C12A—C7A—C8A	110.7 (6)
C12—C7—H7	106.2	C6A—C7A—H7A1	106.1
C6—C7—H7	106.2	C12A—C7A—H7A1	106.1
C8—C7—H7	106.2	C8A—C7A—H7A1	106.1
C14—C8—C15	108.8 (7)	C14A—C8A—C9A	107.6 (6)
C14—C8—C9	110.2 (7)	C14A—C8A—C15A	107.6 (6)
C15—C8—C9	109.0 (7)	C9A—C8A—C15A	110.3 (6)
C14—C8—C7	109.3 (6)	C14A—C8A—C7A	108.5 (6)
C15—C8—C7	107.4 (6)	C9A—C8A—C7A	112.9 (6)
C9—C8—C7	112.0 (6)	C15A—C8A—C7A	109.7 (6)
C10—C9—C8	118.1 (7)	C8A—C9A—C10A	118.4 (7)
C10—C9—H9A	107.8	C8A—C9A—H9A1	107.7
C8—C9—H9A	107.8	C10A—C9A—H9A1	107.7
C10—C9—H9B	107.8	C8A—C9A—H9A2	107.7
C8—C9—H9B	107.8	C10A—C9A—H9A2	107.7
H9A—C9—H9B	107.1	H9A1—C9A—H9A2	107.1
C9—C10—C11	113.4 (7)	C11A—C10A—C9A	113.2 (7)
C9—C10—H10A	108.9	C11A—C10A—H10C	108.9
C11—C10—H10A	108.9	C9A—C10A—H10C	108.9
C9—C10—H10B	108.9	C11A—C10A—H10D	108.9
C11—C10—H10B	108.9	C9A—C10A—H10D	108.9
H10A—C10—H10B	107.7	H10C—C10A—H10D	107.7
C1—C11—C10	116.0 (7)	C10A—C11A—C1A	116.8 (7)
C1—C11—H11A	108.3	C10A—C11A—H11C	108.1
C10—C11—H11A	108.3	C1A—C11A—H11C	108.1
C1—C11—H11B	108.3	C10A—C11A—H11D	108.1
C10—C11—H11B	108.3	C1A—C11A—H11D	108.1
H11A—C11—H11B	107.4	H11C—C11A—H11D	107.3
O1—C12—C7	118.5 (7)	O2—C12A—C7A	120.0 (7)
O1—C12—C1	120.7 (7)	O2—C12A—C1A	119.0 (7)
C7—C12—C1	120.6 (6)	C7A—C12A—C1A	121.0 (6)
C1—C13—H13A	109.5	C1A—C13A—H13D	109.5
C1—C13—H13B	109.5	C1A—C13A—H13E	109.5
H13A—C13—H13B	109.5	H13D—C13A—H13E	109.5
C1—C13—H13C	109.5	C1A—C13A—H13F	109.5
H13A—C13—H13C	109.5	H13D—C13A—H13F	109.5
H13B—C13—H13C	109.5	H13E—C13A—H13F	109.5
C8—C14—H14A	109.5	C8A—C14A—H14D	109.5
C8—C14—H14B	109.5	C8A—C14A—H14E	109.5
H14A—C14—H14B	109.5	H14D—C14A—H14E	109.5
C8—C14—H14C	109.5	C8A—C14A—H14F	109.5
H14A—C14—H14C	109.5	H14D—C14A—H14F	109.5
H14B—C14—H14C	109.5	H14E—C14A—H14F	109.5
C8—C15—H15A	109.5	C8A—C15A—H15D	109.5
C8—C15—H15B	109.5	C8A—C15A—H15E	109.5
H15A—C15—H15B	109.5	H15D—C15A—H15E	109.5
C8—C15—H15C	109.5	C8A—C15A—H15F	109.5
H15A—C15—H15C	109.5	H15D—C15A—H15F	109.5
H15B—C15—H15C	109.5	H15E—C15A—H15F	109.5
C4—C16—H16A	109.5	C4A—C16A—H16D	109.5
C4—C16—H16B	109.5	C4A—C16A—H16E	109.5
H16A—C16—H16B	109.5	H16D—C16A—H16E	109.5
C4—C16—H16C	109.5	C4A—C16A—H16F	109.5
H16A—C16—H16C	109.5	H16D—C16A—H16F	109.5
H16B—C16—H16C	109.5	H16E—C16A—H16F	109.5