(1S,2R,8R)-2,2-Dichloro-3,7,7,10-tetra-methyltricyclo-[6.4.0.0]dodec-10-en-9-one.

The title compound, C(16)H(22)Cl(2)O, was synthesized from β-himachalene, which was isolated from essential oil of the Atlas cedar (cedrus atlantica). The asymmetric unit contains two independent mol-ecules, in each of which the six-membered ring shows a half-chair conformation, whereas the seven-membered ring displays a boat conformation. The dihedral angle between the two rings is slightly different in the two mol-ecules [63.22 (13) and 61.81 (14)°].

Related literature

For the isolation of β-himachalene, see: Joseph & Dev (1968 ▶); Plattier & Teiseire (1974 ▶). For the reactivity of this sesquiterpene, see: Lassaba et al. (1998 ▶); Chekroun et al. (2000 ▶); El Jamili et al. (2002 ▶); Sbai et al. (2002 ▶); Dakir et al. (2004 ▶). For its biological activity, see: Daoubi et al. (2004 ▶).

Experimental

Crystal data

C16H22Cl2O

M = 301.24

Monoclinic,

a = 6.6680 (7) Å

b = 18.7760 (16) Å

c = 12.7696 (12) Å

β = 90.430 (3)°

V = 1598.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 298 K

0.27 × 0.18 × 0.12 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

11524 measured reflections

5817 independent reflections

4348 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.094

S = 1.00

5817 reflections

351 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack & Bernardinelli (2000 ▶), 1791 Friedel pairs

Flack parameter: 0.01 (5)

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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040213/im2235sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040213/im2235Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H22Cl2O	F(000) = 640
Mr = 301.24	Dx = 1.252 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 11524 reflections
a = 6.6680 (7) Å	θ = 2.3–28.2°
b = 18.7760 (16) Å	µ = 0.40 mm−1
c = 12.7696 (12) Å	T = 298 K
β = 90.430 (3)°	Prism, colourless
V = 1598.7 (3) Å3	0.27 × 0.18 × 0.12 mm
Z = 4

Bruker X8 APEXII CCD area-detector diffractometer	4348 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 28.2°, θmin = 2.7°
φ and ω scans	h = −8→8
11524 measured reflections	k = −16→24
5817 independent reflections	l = −14→17

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0451P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
5817 reflections	Δρmax = 0.17 e Å−3
351 parameters	Δρmin = −0.17 e Å−3
1 restraint	Absolute structure: Flack & Bernardinelli (2000), 1791 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (5)

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.

	x	y	z	Uiso*/Ueq
C4	0.2648 (4)	0.51700 (18)	0.1518 (2)	0.0665 (8)
H4	0.3713	0.5344	0.1916	0.080*
C5	0.3032 (4)	0.50170 (17)	0.0397 (2)	0.0566 (7)
H5A	0.3645	0.4551	0.0335	0.068*
H5B	0.3967	0.5366	0.0125	0.068*
C6	0.1141 (4)	0.50357 (13)	−0.02434 (19)	0.0428 (5)
C7	0.1190 (4)	0.50653 (15)	−0.1455 (2)	0.0555 (7)
C13	0.3194 (5)	0.5040 (2)	−0.2006 (3)	0.0842 (11)
H13A	0.3063	0.5251	−0.2688	0.126*
H13B	0.3615	0.4553	−0.2077	0.126*
H13C	0.4173	0.5298	−0.1603	0.126*
C29	0.7542 (5)	0.3406 (2)	0.3751 (3)	0.0802 (10)
H29A	0.7532	0.3825	0.3320	0.120*
H29B	0.7934	0.3003	0.3338	0.120*
H29C	0.8478	0.3469	0.4318	0.120*
C30	0.1340 (6)	0.1455 (2)	0.4271 (3)	0.1001 (13)
H30A	0.0623	0.1353	0.4903	0.150*
H30B	0.1376	0.1036	0.3841	0.150*
H30C	0.0677	0.1832	0.3898	0.150*
C32	0.4841 (4)	0.36421 (13)	0.51889 (19)	0.0483 (6)
Cl2	0.23340 (15)	0.64403 (4)	−0.07935 (7)	0.0867 (3)
Cl3	0.24108 (11)	0.40022 (3)	0.53257 (6)	0.0636 (2)
Cl4	0.65593 (14)	0.42095 (4)	0.58207 (7)	0.0779 (2)
C1	−0.0602 (3)	0.46308 (12)	0.02462 (19)	0.0401 (5)
H1	−0.1815	0.4787	−0.0126	0.048*
C2	−0.0857 (4)	0.48562 (13)	0.1377 (2)	0.0478 (6)
C3	0.0909 (4)	0.50787 (16)	0.1996 (2)	0.0577 (7)
C8	−0.0460 (5)	0.46708 (15)	−0.2027 (2)	0.0635 (8)
H8A	−0.0446	0.4806	−0.2760	0.076*
H8B	−0.1744	0.4812	−0.1742	0.076*
C9	−0.0246 (6)	0.38591 (16)	−0.1941 (2)	0.0753 (9)
H9A	−0.1549	0.3645	−0.2070	0.090*
H9B	0.0644	0.3698	−0.2490	0.090*
C10	0.0552 (5)	0.35865 (15)	−0.0899 (2)	0.0681 (8)
H10A	0.1938	0.3738	−0.0837	0.082*
H10B	0.0560	0.3070	−0.0933	0.082*
C11	−0.0502 (4)	0.37973 (13)	0.0114 (2)	0.0476 (6)
C12	0.0569 (6)	0.52838 (19)	0.3121 (2)	0.0791 (10)
H12A	0.1817	0.5263	0.3499	0.119*
H12B	−0.0371	0.4960	0.3430	0.119*
H12C	0.0043	0.5759	0.3151	0.119*
C14	−0.2671 (5)	0.35177 (17)	0.0103 (3)	0.0793 (10)
H14A	−0.2660	0.3008	0.0045	0.119*
H14B	−0.3383	0.3718	−0.0483	0.119*
H14C	−0.3322	0.3653	0.0741	0.119*
C15	0.0620 (5)	0.34352 (16)	0.1020 (3)	0.0709 (9)
H15A	0.0584	0.2928	0.0925	0.106*
H15B	−0.0008	0.3557	0.1670	0.106*
H15C	0.1989	0.3594	0.1032	0.106*
C16	0.0640 (4)	0.57190 (14)	−0.0831 (2)	0.0545 (7)
C17	0.3373 (3)	0.23635 (12)	0.52663 (18)	0.0416 (5)
H17	0.2229	0.2643	0.5009	0.050*
C18	0.2929 (4)	0.21847 (13)	0.6403 (2)	0.0491 (6)
C19	0.4595 (4)	0.21347 (15)	0.7164 (2)	0.0566 (7)
C20	0.6448 (4)	0.23164 (15)	0.6869 (2)	0.0541 (7)
H20	0.7473	0.2279	0.7364	0.065*
C21	0.6985 (4)	0.25743 (14)	0.5803 (2)	0.0504 (6)
H21A	0.7596	0.2188	0.5415	0.060*
H21B	0.7965	0.2954	0.5867	0.060*
C22	0.5185 (4)	0.28455 (12)	0.51998 (19)	0.0394 (5)
C23	0.5449 (4)	0.32811 (15)	0.41890 (19)	0.0503 (6)
C24	0.3892 (5)	0.31700 (17)	0.3332 (2)	0.0620 (8)
H24A	0.4055	0.3534	0.2801	0.074*
H24B	0.2564	0.3223	0.3627	0.074*
C25	0.4058 (6)	0.2439 (2)	0.2822 (2)	0.0831 (10)
H25A	0.5018	0.2470	0.2256	0.100*
H25B	0.2768	0.2320	0.2513	0.100*
C26	0.4694 (5)	0.18318 (19)	0.3547 (3)	0.0788 (10)
H26A	0.6073	0.1919	0.3757	0.095*
H26B	0.4690	0.1398	0.3135	0.095*
C27	0.3494 (4)	0.16840 (15)	0.4547 (2)	0.0612 (8)
C28	0.4103 (5)	0.1891 (2)	0.8254 (3)	0.0821 (10)
H28A	0.5294	0.1903	0.8681	0.123*
H28B	0.3590	0.1414	0.8230	0.123*
H28C	0.3112	0.2201	0.8549	0.123*
C31	0.4526 (6)	0.10533 (17)	0.5119 (3)	0.0908 (11)
H31A	0.5875	0.1184	0.5304	0.136*
H31B	0.4548	0.0646	0.4665	0.136*
H31C	0.3795	0.0940	0.5742	0.136*
O1	−0.2520 (3)	0.48319 (13)	0.17818 (16)	0.0732 (6)
O2	0.1224 (3)	0.20740 (13)	0.66801 (17)	0.0771 (6)
Cl1	−0.18216 (13)	0.60662 (4)	−0.08502 (7)	0.0734 (2)

	U11	U22	U33	U12	U13	U23
C4	0.0487 (17)	0.085 (2)	0.065 (2)	−0.0084 (15)	−0.0153 (14)	−0.0067 (17)
C5	0.0387 (14)	0.0655 (18)	0.0656 (18)	−0.0037 (12)	−0.0004 (12)	−0.0059 (14)
C6	0.0402 (13)	0.0434 (13)	0.0447 (14)	−0.0043 (10)	−0.0006 (11)	−0.0034 (11)
C7	0.0677 (18)	0.0501 (15)	0.0489 (16)	−0.0119 (13)	0.0092 (13)	−0.0005 (12)
C13	0.092 (3)	0.089 (3)	0.072 (2)	−0.019 (2)	0.0332 (19)	−0.0136 (19)
C29	0.072 (2)	0.100 (3)	0.070 (2)	−0.0123 (19)	0.0127 (17)	0.0220 (19)
C30	0.077 (2)	0.087 (3)	0.137 (3)	−0.019 (2)	−0.014 (2)	−0.052 (3)
C32	0.0542 (15)	0.0398 (13)	0.0506 (16)	0.0004 (11)	−0.0125 (12)	0.0009 (11)
Cl2	0.1082 (7)	0.0573 (5)	0.0947 (6)	−0.0378 (5)	0.0078 (5)	−0.0006 (4)
Cl3	0.0704 (5)	0.0544 (4)	0.0658 (4)	0.0229 (3)	−0.0103 (3)	−0.0051 (3)
Cl4	0.0927 (6)	0.0486 (4)	0.0918 (6)	−0.0169 (4)	−0.0318 (4)	−0.0002 (4)
C1	0.0353 (13)	0.0399 (13)	0.0449 (14)	0.0020 (10)	−0.0076 (10)	0.0039 (11)
C2	0.0454 (15)	0.0471 (14)	0.0511 (16)	0.0094 (11)	0.0035 (12)	0.0059 (12)
C3	0.0539 (18)	0.0667 (18)	0.0522 (16)	0.0042 (14)	−0.0065 (13)	−0.0101 (14)
C8	0.089 (2)	0.0588 (17)	0.0430 (15)	−0.0148 (15)	−0.0073 (14)	−0.0008 (13)
C9	0.118 (3)	0.0553 (18)	0.0527 (17)	−0.0167 (18)	−0.0016 (17)	−0.0117 (14)
C10	0.091 (2)	0.0446 (16)	0.069 (2)	0.0051 (15)	−0.0035 (16)	−0.0075 (14)
C11	0.0488 (15)	0.0406 (13)	0.0532 (15)	−0.0014 (11)	−0.0020 (12)	0.0025 (11)
C12	0.105 (3)	0.080 (2)	0.0529 (18)	−0.003 (2)	−0.0018 (17)	−0.0074 (16)
C14	0.075 (2)	0.0495 (17)	0.114 (3)	−0.0145 (15)	−0.0048 (19)	0.0074 (17)
C15	0.081 (2)	0.0552 (17)	0.076 (2)	0.0137 (15)	−0.0104 (17)	0.0120 (15)
C16	0.0626 (18)	0.0459 (14)	0.0549 (17)	−0.0149 (13)	−0.0024 (13)	−0.0026 (13)
C17	0.0348 (13)	0.0408 (13)	0.0490 (15)	0.0067 (10)	−0.0050 (10)	−0.0034 (11)
C18	0.0430 (15)	0.0421 (14)	0.0624 (17)	0.0073 (11)	0.0050 (12)	0.0054 (12)
C19	0.0551 (17)	0.0587 (17)	0.0559 (17)	0.0108 (13)	−0.0002 (13)	0.0135 (13)
C20	0.0510 (16)	0.0544 (15)	0.0566 (17)	0.0087 (12)	−0.0141 (13)	0.0066 (13)
C21	0.0460 (15)	0.0466 (14)	0.0584 (17)	0.0029 (11)	−0.0054 (12)	0.0061 (12)
C22	0.0378 (13)	0.0395 (12)	0.0410 (13)	0.0040 (10)	−0.0019 (10)	−0.0007 (10)
C23	0.0494 (16)	0.0582 (16)	0.0433 (14)	0.0008 (12)	−0.0001 (12)	0.0077 (13)
C24	0.070 (2)	0.0738 (19)	0.0416 (15)	0.0087 (15)	−0.0054 (13)	0.0035 (15)
C25	0.102 (3)	0.098 (3)	0.0487 (18)	0.011 (2)	−0.0075 (17)	−0.0172 (18)
C26	0.088 (2)	0.073 (2)	0.076 (2)	0.0114 (18)	0.0056 (18)	−0.0394 (18)
C27	0.0563 (17)	0.0455 (15)	0.082 (2)	−0.0012 (12)	−0.0020 (15)	−0.0182 (15)
C28	0.090 (2)	0.090 (3)	0.066 (2)	0.015 (2)	0.0108 (18)	0.0236 (19)
C31	0.097 (3)	0.0443 (17)	0.131 (3)	0.0114 (18)	0.003 (2)	−0.010 (2)
O1	0.0502 (12)	0.1049 (17)	0.0647 (13)	0.0081 (11)	0.0127 (10)	0.0001 (12)
O2	0.0439 (12)	0.0959 (17)	0.0917 (16)	0.0044 (11)	0.0137 (10)	0.0280 (13)
Cl1	0.0823 (6)	0.0530 (4)	0.0846 (5)	0.0118 (4)	−0.0146 (4)	0.0132 (4)

C4—C3	1.326 (4)	C11—C15	1.532 (4)
C4—C5	1.484 (4)	C11—C14	1.538 (4)
C4—H4	0.9300	C12—H12A	0.9600
C5—C6	1.498 (4)	C12—H12B	0.9600
C5—H5A	0.9700	C12—H12C	0.9600
C5—H5B	0.9700	C14—H14A	0.9600
C6—C16	1.522 (4)	C14—H14B	0.9600
C6—C1	1.527 (3)	C14—H14C	0.9600
C6—C7	1.549 (4)	C15—H15A	0.9600
C7—C16	1.510 (4)	C15—H15B	0.9600
C7—C8	1.510 (4)	C15—H15C	0.9600
C7—C13	1.516 (4)	C16—Cl1	1.766 (3)
C13—H13A	0.9600	C17—C22	1.513 (3)
C13—H13B	0.9600	C17—C18	1.521 (4)
C13—H13C	0.9600	C17—C27	1.574 (3)
C29—C23	1.526 (4)	C17—H17	0.9800
C29—H29A	0.9600	C18—O2	1.211 (3)
C29—H29B	0.9600	C18—C19	1.473 (4)
C29—H29C	0.9600	C19—C20	1.339 (4)
C30—C27	1.537 (4)	C19—C28	1.505 (4)
C30—H30A	0.9600	C20—C21	1.491 (4)
C30—H30B	0.9600	C20—H20	0.9300
C30—H30C	0.9600	C21—C22	1.509 (3)
C32—C23	1.504 (4)	C21—H21A	0.9700
C32—C22	1.513 (3)	C21—H21B	0.9700
C32—Cl4	1.756 (3)	C22—C23	1.539 (3)
C32—Cl3	1.766 (3)	C23—C24	1.517 (4)
Cl2—C16	1.764 (3)	C24—C25	1.523 (5)
C1—C2	1.515 (4)	C24—H24A	0.9700
C1—C11	1.576 (3)	C24—H24B	0.9700
C1—H1	0.9800	C25—C26	1.527 (5)
C2—O1	1.228 (3)	C25—H25A	0.9700
C2—C3	1.474 (4)	C25—H25B	0.9700
C3—C12	1.506 (4)	C26—C27	1.537 (5)
C8—C9	1.535 (4)	C26—H26A	0.9700
C8—H8A	0.9700	C26—H26B	0.9700
C8—H8B	0.9700	C27—C31	1.549 (5)
C9—C10	1.519 (4)	C28—H28A	0.9600
C9—H9A	0.9700	C28—H28B	0.9600
C9—H9B	0.9700	C28—H28C	0.9600
C10—C11	1.529 (4)	C31—H31A	0.9600
C10—H10A	0.9700	C31—H31B	0.9600
C10—H10B	0.9700	C31—H31C	0.9600
C3—C4—C5	125.3 (3)	C11—C14—H14A	109.5
C3—C4—H4	117.4	C11—C14—H14B	109.5
C5—C4—H4	117.4	H14A—C14—H14B	109.5
C4—C5—C6	111.8 (2)	C11—C14—H14C	109.5
C4—C5—H5A	109.3	H14A—C14—H14C	109.5
C6—C5—H5A	109.3	H14B—C14—H14C	109.5
C4—C5—H5B	109.3	C11—C15—H15A	109.5
C6—C5—H5B	109.3	C11—C15—H15B	109.5
H5A—C5—H5B	107.9	H15A—C15—H15B	109.5
C5—C6—C16	118.0 (2)	C11—C15—H15C	109.5
C5—C6—C1	113.9 (2)	H15A—C15—H15C	109.5
C16—C6—C1	117.1 (2)	H15B—C15—H15C	109.5
C5—C6—C7	121.5 (2)	C7—C16—C6	61.42 (18)
C16—C6—C7	58.90 (17)	C7—C16—Cl2	118.7 (2)
C1—C6—C7	116.6 (2)	C6—C16—Cl2	119.7 (2)
C16—C7—C8	118.4 (3)	C7—C16—Cl1	121.5 (2)
C16—C7—C13	119.3 (3)	C6—C16—Cl1	121.25 (19)
C8—C7—C13	113.7 (3)	Cl2—C16—Cl1	108.17 (15)
C16—C7—C6	59.67 (17)	C22—C17—C18	110.30 (19)
C8—C7—C6	116.4 (2)	C22—C17—C27	114.06 (19)
C13—C7—C6	119.2 (3)	C18—C17—C27	112.9 (2)
C7—C13—H13A	109.5	C22—C17—H17	106.3
C7—C13—H13B	109.5	C18—C17—H17	106.3
H13A—C13—H13B	109.5	C27—C17—H17	106.3
C7—C13—H13C	109.5	O2—C18—C19	120.1 (2)
H13A—C13—H13C	109.5	O2—C18—C17	120.4 (2)
H13B—C13—H13C	109.5	C19—C18—C17	119.5 (2)
C23—C29—H29A	109.5	C20—C19—C18	119.4 (2)
C23—C29—H29B	109.5	C20—C19—C28	123.1 (3)
H29A—C29—H29B	109.5	C18—C19—C28	117.5 (3)
C23—C29—H29C	109.5	C19—C20—C21	124.6 (2)
H29A—C29—H29C	109.5	C19—C20—H20	117.7
H29B—C29—H29C	109.5	C21—C20—H20	117.7
C27—C30—H30A	109.5	C20—C21—C22	112.3 (2)
C27—C30—H30B	109.5	C20—C21—H21A	109.1
H30A—C30—H30B	109.5	C22—C21—H21A	109.1
C27—C30—H30C	109.5	C20—C21—H21B	109.1
H30A—C30—H30C	109.5	C22—C21—H21B	109.1
H30B—C30—H30C	109.5	H21A—C21—H21B	107.9
C23—C32—C22	61.35 (17)	C21—C22—C17	113.7 (2)
C23—C32—Cl4	118.95 (19)	C21—C22—C32	117.3 (2)
C22—C32—Cl4	119.78 (18)	C17—C22—C32	118.1 (2)
C23—C32—Cl3	120.68 (18)	C21—C22—C23	120.8 (2)
C22—C32—Cl3	121.13 (18)	C17—C22—C23	117.5 (2)
Cl4—C32—Cl3	108.56 (14)	C32—C22—C23	59.02 (17)
C2—C1—C6	110.0 (2)	C32—C23—C24	119.1 (2)
C2—C1—C11	112.6 (2)	C32—C23—C29	119.7 (3)
C6—C1—C11	114.7 (2)	C24—C23—C29	112.3 (2)
C2—C1—H1	106.3	C32—C23—C22	59.62 (15)
C6—C1—H1	106.3	C24—C23—C22	116.7 (2)
C11—C1—H1	106.3	C29—C23—C22	120.0 (2)
O1—C2—C3	120.3 (2)	C23—C24—C25	112.4 (3)
O1—C2—C1	119.9 (2)	C23—C24—H24A	109.1
C3—C2—C1	119.7 (2)	C25—C24—H24A	109.1
C4—C3—C2	119.2 (3)	C23—C24—H24B	109.1
C4—C3—C12	123.0 (3)	C25—C24—H24B	109.1
C2—C3—C12	117.3 (2)	H24A—C24—H24B	107.9
C7—C8—C9	112.7 (3)	C24—C25—C26	115.7 (3)
C7—C8—H8A	109.1	C24—C25—H25A	108.3
C9—C8—H8A	109.1	C26—C25—H25A	108.3
C7—C8—H8B	109.1	C24—C25—H25B	108.3
C9—C8—H8B	109.1	C26—C25—H25B	108.3
H8A—C8—H8B	107.8	H25A—C25—H25B	107.4
C10—C9—C8	115.4 (2)	C25—C26—C27	119.7 (3)
C10—C9—H9A	108.4	C25—C26—H26A	107.4
C8—C9—H9A	108.4	C27—C26—H26A	107.4
C10—C9—H9B	108.4	C25—C26—H26B	107.4
C8—C9—H9B	108.4	C27—C26—H26B	107.4
H9A—C9—H9B	107.5	H26A—C26—H26B	106.9
C9—C10—C11	119.6 (3)	C30—C27—C26	110.6 (3)
C9—C10—H10A	107.4	C30—C27—C31	107.7 (3)
C11—C10—H10A	107.4	C26—C27—C31	107.3 (3)
C9—C10—H10B	107.4	C30—C27—C17	108.0 (2)
C11—C10—H10B	107.4	C26—C27—C17	111.6 (2)
H10A—C10—H10B	106.9	C31—C27—C17	111.7 (3)
C10—C11—C15	107.4 (2)	C19—C28—H28A	109.5
C10—C11—C14	110.0 (2)	C19—C28—H28B	109.5
C15—C11—C14	108.0 (2)	H28A—C28—H28B	109.5
C10—C11—C1	111.6 (2)	C19—C28—H28C	109.5
C15—C11—C1	112.4 (2)	H28A—C28—H28C	109.5
C14—C11—C1	107.4 (2)	H28B—C28—H28C	109.5
C3—C12—H12A	109.5	C27—C31—H31A	109.5
C3—C12—H12B	109.5	C27—C31—H31B	109.5
H12A—C12—H12B	109.5	H31A—C31—H31B	109.5
C3—C12—H12C	109.5	C27—C31—H31C	109.5
H12A—C12—H12C	109.5	H31A—C31—H31C	109.5
H12B—C12—H12C	109.5	H31B—C31—H31C	109.5