1-[(1S,6R,7S,9R)-8,8-Di-bromo-5,5,9-tri-methyl-tri-cyclo-[4.4.0.1(7,9)]decan-1-yl]ethanone.

The title compound, C16H24Br2O, was synthesized by three steps from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from essential oil of the Atlas cedar cedrus atlantica. The asymmetric unit contains two independent mol-ecules with almost identical conformations. Each mol-ecule is built up from two fused six-membered rings, one having a chair conformation and the other a boat conformation, and an additional three-membered ring arising from the reaction of himachalene with di-bromo-carbene. In the crystal, there are no significant intermolecular interactions present. The absolute structure of the title compound was confirmed by resonance scattering.

Related literature

For background to the reactivity and biological properties of β-himachalene, see: El Haib et al. (2011 ▶); El Jamili et al. (2002 ▶); Daoubi et al. (2004 ▶). For a related structure, see: Benharref et al. (2013 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H24Br2O

M = 392.17

Orthorhombic,

a = 13.5013 (19) Å

b = 14.042 (2) Å

c = 17.213 (3) Å

V = 3263.3 (8) Å3

Z = 8

Mo Kα radiation

μ = 4.96 mm−1

T = 298 K

0.5 × 0.03 × 0.03 mm

Data collection

Bruker X8 APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009) T min = 0.557, T max = 0.747

22468 measured reflections

6542 independent reflections

5262 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.060

S = 1.02

6540 reflections

351 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.39 e Å−3

Absolute structure: Flack & Bernardinelli (2000 ▶)

Absolute structure parameter: −0.005 (8)

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 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814005431/bt6967sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005431/bt6967Isup2.hkl

CCDC reference: 990889

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

C16H24Br2O	Dx = 1.596 Mg m−3
Mr = 392.17	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 6542 reflections
a = 13.5013 (19) Å	θ = 2.4–26.4°
b = 14.042 (2) Å	µ = 4.96 mm−1
c = 17.213 (3) Å	T = 298 K
V = 3263.3 (8) Å3	Block, colourless
Z = 8	0.5 × 0.03 × 0.03 mm
F(000) = 1584

Bruker X8 APEX CCD area-detector diffractometer	6542 independent reflections
Radiation source: fine-focus sealed tube	5262 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→16
Tmin = 0.557, Tmax = 0.747	k = −12→17
22468 measured reflections	l = −17→21

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.060	w = 1/[σ2(Fo2) + (0.0104P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
6540 reflections	Δρmax = 0.27 e Å−3
351 parameters	Δρmin = −0.39 e Å−3
0 restraints	Absolute structure: Flack & Bernardinelli (2000)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.005 (8)

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.

	x	y	z	Uiso*/Ueq
C1	0.7516 (2)	1.0732 (2)	−0.03701 (18)	0.0342 (8)
C2	0.6483 (3)	1.1166 (3)	−0.0456 (2)	0.0518 (10)
H2A	0.6508	1.1658	−0.0851	0.062*
H2B	0.6032	1.0676	−0.0636	0.062*
C3	0.6068 (3)	1.1596 (3)	0.0284 (2)	0.0628 (12)
H3A	0.6465	1.2142	0.0431	0.075*
H3B	0.5398	1.1815	0.0189	0.075*
C4	0.6060 (3)	1.0889 (3)	0.0941 (2)	0.0544 (10)
H4A	0.5600	1.0379	0.0819	0.065*
H4B	0.5827	1.1202	0.1409	0.065*
C5	0.7090 (2)	1.0460 (3)	0.10960 (19)	0.0394 (9)
C6	0.7513 (2)	1.0035 (2)	0.03386 (15)	0.0250 (7)
H6	0.8204	0.9864	0.0442	0.030*
C7	0.6976 (2)	0.9125 (2)	0.01156 (17)	0.0298 (8)
H7	0.6264	0.9124	0.0228	0.036*
C8	0.7455 (2)	0.8170 (2)	0.01354 (18)	0.0329 (8)
C9	0.7266 (2)	0.8636 (2)	−0.06406 (17)	0.0320 (8)
C10	0.8094 (2)	0.9159 (2)	−0.1044 (2)	0.0393 (9)
H10A	0.8216	0.8877	−0.1549	0.047*
H10B	0.8696	0.9114	−0.0739	0.047*
C11	0.7797 (3)	1.0195 (3)	−0.11368 (18)	0.0435 (9)
H11A	0.7235	1.0225	−0.1488	0.052*
H11B	0.8340	1.0532	−0.1382	0.052*
C12	0.8323 (3)	1.1502 (3)	−0.0304 (2)	0.0452 (9)
C13	0.9368 (3)	1.1193 (3)	−0.0122 (2)	0.0568 (11)
H13A	0.9824	1.1549	−0.0437	0.085*
H13B	0.9439	1.0526	−0.0231	0.085*
H13C	0.9506	1.1309	0.0417	0.085*
C14	0.7777 (3)	1.1229 (3)	0.1434 (2)	0.0547 (11)
H14A	0.7492	1.1479	0.1902	0.082*
H14B	0.7855	1.1734	0.1062	0.082*
H14C	0.8412	1.0955	0.1547	0.082*
C15	0.6990 (3)	0.9672 (3)	0.1702 (2)	0.0553 (11)
H15A	0.6551	0.9188	0.1512	0.083*
H15B	0.6728	0.9935	0.2175	0.083*
H15C	0.7629	0.9398	0.1802	0.083*
C16	0.6480 (3)	0.8239 (3)	−0.1165 (2)	0.0517 (10)
H16A	0.6738	0.7697	−0.1438	0.077*
H16B	0.6282	0.8717	−0.1532	0.077*
H16C	0.5918	0.8049	−0.0861	0.077*
Br1	0.87872 (2)	0.80148 (3)	0.05270 (2)	0.04524 (10)
Br2	0.66521 (3)	0.71109 (3)	0.04601 (3)	0.05635 (12)
O1	0.8142 (2)	1.23284 (19)	−0.04537 (18)	0.0746 (9)
C17	0.8403 (2)	0.5321 (2)	0.30776 (18)	0.0353 (8)
C18	0.9200 (3)	0.4590 (3)	0.3290 (2)	0.0536 (11)
H18A	0.9638	0.4872	0.3674	0.064*
H18B	0.8881	0.4046	0.3531	0.064*
C19	0.9822 (3)	0.4239 (3)	0.2615 (2)	0.0645 (12)
H19A	1.0214	0.4762	0.2412	0.077*
H19B	1.0274	0.3750	0.2796	0.077*
C20	0.9176 (3)	0.3837 (3)	0.1974 (2)	0.0532 (10)
H20A	0.8836	0.3276	0.2166	0.064*
H20B	0.9593	0.3643	0.1543	0.064*
C21	0.8409 (2)	0.4558 (2)	0.16839 (19)	0.0358 (8)
C22	0.7784 (2)	0.4940 (2)	0.23762 (17)	0.0297 (7)
H22	0.7397	0.5479	0.2178	0.036*
C23	0.7047 (2)	0.4204 (2)	0.26590 (18)	0.0319 (8)
H23	0.7282	0.3544	0.2648	0.038*
C24	0.5956 (2)	0.4328 (2)	0.25512 (19)	0.0365 (8)
C25	0.6391 (2)	0.4460 (2)	0.33457 (19)	0.0331 (8)
C26	0.6622 (2)	0.5442 (3)	0.3653 (2)	0.0411 (9)
H26A	0.6258	0.5554	0.4130	0.049*
H26B	0.6426	0.5920	0.3276	0.049*
C27	0.7733 (2)	0.5508 (3)	0.38072 (18)	0.0437 (9)
H27A	0.7906	0.5052	0.4208	0.052*
H27B	0.7880	0.6139	0.4007	0.052*
C28	0.8851 (3)	0.6296 (3)	0.2910 (2)	0.0501 (10)
C29	0.8180 (3)	0.7092 (3)	0.2652 (2)	0.0614 (11)
H29A	0.8507	0.7691	0.2729	0.092*
H29B	0.7580	0.7077	0.2951	0.092*
H29C	0.8024	0.7014	0.2112	0.092*
C30	0.8932 (3)	0.5378 (3)	0.1257 (2)	0.0517 (10)
H30A	0.9371	0.5699	0.1609	0.078*
H30B	0.8446	0.5820	0.1067	0.078*
H30C	0.9305	0.5128	0.0828	0.078*
C31	0.7714 (3)	0.4076 (3)	0.1084 (2)	0.0541 (11)
H31A	0.8092	0.3880	0.0640	0.081*
H31B	0.7213	0.4521	0.0925	0.081*
H31C	0.7406	0.3530	0.1317	0.081*
C32	0.6193 (3)	0.3715 (3)	0.3973 (2)	0.0520 (10)
H32A	0.5559	0.3833	0.4206	0.078*
H32B	0.6699	0.3751	0.4364	0.078*
H32C	0.6196	0.3091	0.3744	0.078*
Br3	0.54217 (3)	0.53917 (3)	0.19802 (2)	0.04941 (11)
Br4	0.51892 (3)	0.32022 (3)	0.23283 (2)	0.06195 (13)
O2	0.9721 (2)	0.6461 (2)	0.30335 (19)	0.0872 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0425 (19)	0.0318 (19)	0.0284 (19)	−0.0034 (16)	−0.0046 (16)	0.0053 (15)
C2	0.060 (2)	0.041 (2)	0.054 (2)	0.0080 (18)	−0.018 (2)	0.009 (2)
C3	0.048 (2)	0.052 (3)	0.089 (3)	0.025 (2)	−0.011 (2)	−0.007 (2)
C4	0.051 (2)	0.049 (3)	0.063 (3)	0.0153 (19)	0.011 (2)	−0.014 (2)
C5	0.044 (2)	0.040 (2)	0.0341 (19)	0.0017 (17)	0.0072 (16)	−0.0049 (18)
C6	0.0288 (15)	0.0211 (16)	0.0249 (17)	0.0002 (13)	0.0003 (13)	0.0007 (13)
C7	0.0280 (17)	0.030 (2)	0.0310 (18)	0.0021 (14)	0.0019 (14)	−0.0011 (14)
C8	0.0285 (16)	0.0267 (19)	0.0435 (19)	−0.0038 (15)	−0.0005 (15)	0.0008 (15)
C9	0.0354 (18)	0.0330 (19)	0.0277 (18)	−0.0013 (15)	0.0005 (15)	−0.0085 (15)
C10	0.047 (2)	0.041 (2)	0.0297 (19)	−0.0038 (16)	0.0077 (16)	−0.0060 (16)
C11	0.056 (2)	0.043 (2)	0.0315 (19)	−0.0121 (18)	0.0011 (17)	0.0059 (17)
C12	0.069 (3)	0.034 (2)	0.033 (2)	−0.0144 (19)	0.0010 (19)	0.0014 (17)
C13	0.054 (2)	0.052 (3)	0.064 (3)	−0.024 (2)	0.006 (2)	0.001 (2)
C14	0.067 (3)	0.055 (3)	0.042 (2)	−0.004 (2)	0.003 (2)	−0.0179 (19)
C15	0.077 (3)	0.060 (3)	0.0290 (19)	−0.002 (2)	0.0176 (19)	−0.001 (2)
C16	0.054 (2)	0.047 (2)	0.054 (2)	−0.0055 (19)	−0.0146 (19)	−0.0152 (19)
Br1	0.04248 (19)	0.0378 (2)	0.0554 (2)	0.00669 (16)	−0.01088 (17)	0.00135 (19)
Br2	0.0576 (2)	0.0342 (2)	0.0772 (3)	−0.01247 (18)	0.0117 (2)	0.0086 (2)
O1	0.108 (2)	0.0304 (17)	0.086 (2)	−0.0148 (15)	−0.0083 (19)	0.0137 (15)
C17	0.0281 (16)	0.042 (2)	0.0356 (18)	−0.0008 (16)	−0.0081 (15)	0.0005 (17)
C18	0.045 (2)	0.069 (3)	0.047 (2)	0.005 (2)	−0.0138 (18)	0.007 (2)
C19	0.041 (2)	0.077 (3)	0.075 (3)	0.023 (2)	−0.003 (2)	0.012 (2)
C20	0.052 (2)	0.046 (2)	0.061 (2)	0.0181 (19)	0.015 (2)	0.002 (2)
C21	0.0389 (18)	0.031 (2)	0.0372 (18)	0.0057 (16)	0.0062 (16)	−0.0015 (16)
C22	0.0327 (17)	0.0252 (18)	0.0312 (17)	0.0045 (14)	0.0006 (14)	0.0011 (14)
C23	0.0324 (17)	0.0258 (19)	0.0374 (19)	0.0012 (14)	−0.0019 (15)	0.0062 (15)
C24	0.0353 (18)	0.0303 (19)	0.044 (2)	−0.0014 (15)	−0.0059 (16)	0.0011 (16)
C25	0.0297 (17)	0.034 (2)	0.0351 (18)	0.0026 (15)	0.0022 (14)	0.0030 (16)
C26	0.045 (2)	0.045 (2)	0.0334 (19)	0.0048 (18)	0.0052 (16)	−0.0004 (17)
C27	0.052 (2)	0.045 (2)	0.034 (2)	−0.0074 (18)	−0.0054 (17)	0.0005 (17)
C28	0.049 (2)	0.054 (3)	0.047 (2)	−0.018 (2)	−0.0040 (19)	−0.0065 (19)
C29	0.086 (3)	0.036 (2)	0.062 (2)	−0.009 (2)	−0.003 (2)	0.004 (2)
C30	0.051 (2)	0.053 (3)	0.051 (2)	0.000 (2)	0.0137 (19)	0.012 (2)
C31	0.061 (2)	0.062 (3)	0.039 (2)	0.001 (2)	0.006 (2)	−0.015 (2)
C32	0.055 (2)	0.054 (2)	0.047 (2)	0.006 (2)	0.009 (2)	0.018 (2)
Br3	0.03866 (19)	0.0577 (3)	0.0519 (2)	0.00694 (18)	−0.00959 (18)	0.01018 (19)
Br4	0.0534 (2)	0.0531 (3)	0.0794 (3)	−0.0209 (2)	−0.0020 (2)	−0.0105 (2)
O2	0.0579 (18)	0.085 (2)	0.119 (3)	−0.0333 (18)	−0.020 (2)	0.004 (2)

C1—C2	1.529 (5)	C17—C28	1.524 (5)
C1—C12	1.540 (5)	C17—C18	1.532 (5)
C1—C6	1.564 (4)	C17—C22	1.563 (4)
C1—C11	1.567 (4)	C17—C27	1.570 (5)
C2—C3	1.516 (5)	C18—C19	1.516 (5)
C2—H2A	0.9700	C18—H18A	0.9700
C2—H2B	0.9700	C18—H18B	0.9700
C3—C4	1.506 (5)	C19—C20	1.515 (5)
C3—H3A	0.9700	C19—H19A	0.9700
C3—H3B	0.9700	C19—H19B	0.9700
C4—C5	1.539 (5)	C20—C21	1.531 (4)
C4—H4A	0.9700	C20—H20A	0.9700
C4—H4B	0.9700	C20—H20B	0.9700
C5—C15	1.527 (5)	C21—C30	1.538 (4)
C5—C14	1.537 (5)	C21—C31	1.550 (5)
C5—C6	1.543 (4)	C21—C22	1.556 (4)
C6—C7	1.519 (4)	C22—C23	1.515 (4)
C6—H6	0.9800	C22—H22	0.9800
C7—C8	1.489 (4)	C23—C24	1.496 (4)
C7—C9	1.523 (4)	C23—C25	1.520 (4)
C7—H7	0.9800	C23—H23	0.9800
C8—C9	1.510 (4)	C24—C25	1.500 (4)
C8—Br2	1.924 (3)	C24—Br4	1.928 (3)
C8—Br1	1.933 (3)	C24—Br3	1.928 (3)
C9—C16	1.501 (4)	C25—C26	1.509 (5)
C9—C10	1.506 (4)	C25—C32	1.528 (4)
C10—C11	1.517 (5)	C26—C27	1.526 (5)
C10—H10A	0.9700	C26—H26A	0.9700
C10—H10B	0.9700	C26—H26B	0.9700
C11—H11A	0.9700	C27—H27A	0.9700
C11—H11B	0.9700	C27—H27B	0.9700
C12—O1	1.213 (4)	C28—O2	1.215 (4)
C12—C13	1.509 (5)	C28—C29	1.506 (5)
C13—H13A	0.9600	C29—H29A	0.9600
C13—H13B	0.9600	C29—H29B	0.9600
C13—H13C	0.9600	C29—H29C	0.9600
C14—H14A	0.9600	C30—H30A	0.9600
C14—H14B	0.9600	C30—H30B	0.9600
C14—H14C	0.9600	C30—H30C	0.9600
C15—H15A	0.9600	C31—H31A	0.9600
C15—H15B	0.9600	C31—H31B	0.9600
C15—H15C	0.9600	C31—H31C	0.9600
C16—H16A	0.9600	C32—H32A	0.9600
C16—H16B	0.9600	C32—H32B	0.9600
C16—H16C	0.9600	C32—H32C	0.9600
C2—C1—C12	111.9 (3)	C28—C17—C18	111.5 (3)
C2—C1—C6	108.8 (3)	C28—C17—C22	112.0 (3)
C12—C1—C6	112.5 (3)	C18—C17—C22	109.3 (3)
C2—C1—C11	109.4 (3)	C28—C17—C27	103.3 (3)
C12—C1—C11	103.3 (3)	C18—C17—C27	109.0 (3)
C6—C1—C11	110.9 (3)	C22—C17—C27	111.6 (2)
C3—C2—C1	114.5 (3)	C19—C18—C17	115.1 (3)
C3—C2—H2A	108.6	C19—C18—H18A	108.5
C1—C2—H2A	108.6	C17—C18—H18A	108.5
C3—C2—H2B	108.6	C19—C18—H18B	108.5
C1—C2—H2B	108.6	C17—C18—H18B	108.5
H2A—C2—H2B	107.6	H18A—C18—H18B	107.5
C4—C3—C2	111.8 (3)	C20—C19—C18	111.1 (3)
C4—C3—H3A	109.3	C20—C19—H19A	109.4
C2—C3—H3A	109.3	C18—C19—H19A	109.4
C4—C3—H3B	109.3	C20—C19—H19B	109.4
C2—C3—H3B	109.3	C18—C19—H19B	109.4
H3A—C3—H3B	107.9	H19A—C19—H19B	108.0
C3—C4—C5	112.4 (3)	C19—C20—C21	112.4 (3)
C3—C4—H4A	109.1	C19—C20—H20A	109.1
C5—C4—H4A	109.1	C21—C20—H20A	109.1
C3—C4—H4B	109.1	C19—C20—H20B	109.1
C5—C4—H4B	109.1	C21—C20—H20B	109.1
H4A—C4—H4B	107.8	H20A—C20—H20B	107.9
C15—C5—C14	107.7 (3)	C20—C21—C30	109.9 (3)
C15—C5—C4	108.8 (3)	C20—C21—C31	109.8 (3)
C14—C5—C4	109.6 (3)	C30—C21—C31	106.6 (3)
C15—C5—C6	109.3 (3)	C20—C21—C22	110.2 (3)
C14—C5—C6	111.6 (3)	C30—C21—C22	110.9 (3)
C4—C5—C6	109.8 (3)	C31—C21—C22	109.4 (3)
C7—C6—C5	111.2 (3)	C23—C22—C21	111.5 (3)
C7—C6—C1	109.3 (2)	C23—C22—C17	109.7 (2)
C5—C6—C1	114.7 (3)	C21—C22—C17	114.8 (2)
C7—C6—H6	107.1	C23—C22—H22	106.8
C5—C6—H6	107.1	C21—C22—H22	106.8
C1—C6—H6	107.1	C17—C22—H22	106.8
C8—C7—C6	123.0 (2)	C24—C23—C22	121.8 (3)
C8—C7—C9	60.1 (2)	C24—C23—C25	59.7 (2)
C6—C7—C9	118.2 (3)	C22—C23—C25	118.1 (3)
C8—C7—H7	114.8	C24—C23—H23	115.3
C6—C7—H7	114.8	C22—C23—H23	115.3
C9—C7—H7	114.8	C25—C23—H23	115.3
C7—C8—C9	61.0 (2)	C23—C24—C25	61.0 (2)
C7—C8—Br2	117.2 (2)	C23—C24—Br4	117.3 (2)
C9—C8—Br2	119.8 (2)	C25—C24—Br4	119.5 (2)
C7—C8—Br1	120.9 (2)	C23—C24—Br3	121.5 (2)
C9—C8—Br1	121.0 (2)	C25—C24—Br3	121.0 (2)
Br2—C8—Br1	109.63 (15)	Br4—C24—Br3	109.45 (15)
C16—C9—C10	115.4 (3)	C24—C25—C26	120.9 (3)
C16—C9—C8	119.4 (3)	C24—C25—C23	59.4 (2)
C10—C9—C8	119.5 (3)	C26—C25—C23	111.6 (3)
C16—C9—C7	120.0 (3)	C24—C25—C32	119.4 (3)
C10—C9—C7	111.4 (3)	C26—C25—C32	114.5 (3)
C8—C9—C7	58.8 (2)	C23—C25—C32	119.3 (3)
C9—C10—C11	108.6 (3)	C25—C26—C27	108.7 (3)
C9—C10—H10A	110.0	C25—C26—H26A	110.0
C11—C10—H10A	110.0	C27—C26—H26A	110.0
C9—C10—H10B	110.0	C25—C26—H26B	110.0
C11—C10—H10B	110.0	C27—C26—H26B	110.0
H10A—C10—H10B	108.3	H26A—C26—H26B	108.3
C10—C11—C1	115.9 (3)	C26—C27—C17	114.6 (3)
C10—C11—H11A	108.3	C26—C27—H27A	108.6
C1—C11—H11A	108.3	C17—C27—H27A	108.6
C10—C11—H11B	108.3	C26—C27—H27B	108.6
C1—C11—H11B	108.3	C17—C27—H27B	108.6
H11A—C11—H11B	107.4	H27A—C27—H27B	107.6
O1—C12—C13	120.5 (4)	O2—C28—C29	119.4 (4)
O1—C12—C1	120.9 (4)	O2—C28—C17	121.5 (4)
C13—C12—C1	118.4 (3)	C29—C28—C17	118.9 (3)
C12—C13—H13A	109.5	C28—C29—H29A	109.5
C12—C13—H13B	109.5	C28—C29—H29B	109.5
H13A—C13—H13B	109.5	H29A—C29—H29B	109.5
C12—C13—H13C	109.5	C28—C29—H29C	109.5
H13A—C13—H13C	109.5	H29A—C29—H29C	109.5
H13B—C13—H13C	109.5	H29B—C29—H29C	109.5
C5—C14—H14A	109.5	C21—C30—H30A	109.5
C5—C14—H14B	109.5	C21—C30—H30B	109.5
H14A—C14—H14B	109.5	H30A—C30—H30B	109.5
C5—C14—H14C	109.5	C21—C30—H30C	109.5
H14A—C14—H14C	109.5	H30A—C30—H30C	109.5
H14B—C14—H14C	109.5	H30B—C30—H30C	109.5
C5—C15—H15A	109.5	C21—C31—H31A	109.5
C5—C15—H15B	109.5	C21—C31—H31B	109.5
H15A—C15—H15B	109.5	H31A—C31—H31B	109.5
C5—C15—H15C	109.5	C21—C31—H31C	109.5
H15A—C15—H15C	109.5	H31A—C31—H31C	109.5
H15B—C15—H15C	109.5	H31B—C31—H31C	109.5
C9—C16—H16A	109.5	C25—C32—H32A	109.5
C9—C16—H16B	109.5	C25—C32—H32B	109.5
H16A—C16—H16B	109.5	H32A—C32—H32B	109.5
C9—C16—H16C	109.5	C25—C32—H32C	109.5
H16A—C16—H16C	109.5	H32A—C32—H32C	109.5
H16B—C16—H16C	109.5	H32B—C32—H32C	109.5