p-Decyl­phenyl isocyanide and p-decyl­benzo­nitrile: isomorphous iso­nitrile/nitrile isomers

p-Decyl­phenyl isocyanide, p-C₁₀H₂₁–C₆H₄–NC or C₁₇H₂₅N, and p-decyl­benzo­nitrile, p-C₁₀H₂₁–C₆H₄–CN or C₁₇H₂₅N, are isomorphous. The mol­ecules lie in mirror planes, with the C₆ rings perpendicular to the mirror. The packing of both mol­ecules includes an aliphatic region, with close to ideal packing of the C₁₀H₂₁ chains, and an aromatic region, with phenyl ring–CN interactions. In addition, the CN ends of the mol­ecules are also involved in a CN...NC dipolar interaction.

S1. Comment

In the course of a study of the structures and properties of a series of [Pt(arylisonitrile)₄][Pt(CN)₄] compounds (Daws et al. 1997), it was felt useful to determine the structure of one of the arylisonitrile ligands, p-decylphenylisocyanide, (I); this structure is reported here. Corresponding nitriles and isocyanides sometimes have different packing arrangements, even though the pairs of molecules are very closely isosteric (Pink et al., 2000, and references therein). In view of this fact, it also seemed worthwhile to determine the structure of p-decylphenylnitrile, (II).

The two compounds are isomorphous. The anisotropic displacement ellipsoids and atom labelling are shown in Fig. 1. The bond lengths and angles in the two molecules agree within experimental error. The C3—N2 and N2—C1 distances in the isocyanide are 1.407 (2) and 1.162 (2) Å, respectively, and the corresponding distances in the nitrile, C3—-C2 and C2—N1, are 1.446 (3) and 1.153 (3) Å, respectively.

There are three major components to the packing, viz. the interactions of the aliphatic portions, the π interactions of the aromatic portions, and the dipolar interactions of the nitrile and isonitrile groups (see Fig. 2 for two orthogonal views of the packing).

The aliphatic C₁₀H₂₁ fragments pack parallel to each other, forming a two-dimensional layer with hexagonal close-packed rods. This arrangement is similar to that found in n-decane (Bond & Davies, 2002). While the packing in n-decane is not identical to that of either of the CN compounds, since the planar C₁₀ groups are oriented differently to each other in the two basically different structures, the cross sectional areas of the rods in the CN compounds [18.26 (2) Ų for –NC and 18.25 (2) Ųfor –CN] are only slightly larger than that in n-decane [17.94 (2) Ų], indicating that this aspect of the packing is only slightly affected by the terminal groups.

The overlap of the aromatic fragments is shown in Fig. 3. There is no overlap between the rings, but the –CN and –NC groups lie directly over the ring in the next layer. The perpendicular distances in (I) are 3.467 (1) (ring), 3.474 (2) (N2) and 3.494 (2) Å (C1). The distances in (II) are 3.474 (2) (ring), 3.506 (4) (C2) and 3.552 (3) Å (N1). In each case, the –NC or –CN group is bent slightly out of the plane of the ring and away from the ring in the next molecule.

There are two pairs of dipolar interactions between a particular –NC or –CN group and its neighbors. One pair is attractive, involving groups related across a center of symmetry. In these interactions, the perpendicular distances between the parallel groups are 4.052 (2) Å for (I) and 4.055 (3) Å for (II). The dipoles are slightly displaced along the C—N bond direction from the positions of maximum attraction, assuming equal and opposite charges localized on the C and N atoms; the displacements are 0.149 Å for (I) and 0.184 Å for (II). The other pair of interactions is repulsive, involving groups related by translation along the a direction. In these interactions, the perpendicular distances between the parallel groups are shorter, viz. 3.525 (2) Å for (I) and 3.557 (3) Å for (II). However, the dipoles are considerably displaced along the C—N bond direction from the positions of maximum repulsion; the displacements are 3.054 (2) Å for (I) and 3.017 (3) Å for (II). The net result is that, for this simple model, the magnitude of the attractive interaction is about three times that of the repulsive interaction.

S2. Experimental

The preparation of (I) has been reported previously (Daws et al., 1997). Crystals suitable for diffraction were prepared by recrystallization from ethanol. Compound (II) was obtained according to the method of Casanova et al. (1966). A 0.23 g sample of neat p-C₁₀H₂₁—C₆H₄—NC was heated to 473 K for 24 h under an argon atmosphere. After cooling overnight, the IR spectrum showed a single band at 2232.5 cm⁻¹, due to the nitrile stretch. No isocyanide was present. The crude nitrile was purified by chromatography on silica gel with a 1:20 mixture of ethyl acetate and hexanes. Recrystallization from a variety of solvents gave crystals inferior to those of (I). The crystals used for the X-ray structure determination were obtained from acetone.

S3. Refinement

For (I), the positions and isotropic displacement parameters for all of the H atoms were refined. For (II), given the lower quality of the data, the H atoms were placed in idealized positions, with C—H distances of 0.95 Å for the aromatic H atoms, 0.99 Å for the CH₂ H atoms and 0.98 Å for the CH₃ H atoms. The U_iso values were set at 1.2U_eq of the attached C atoms for the aromatic and CH₂ H atoms, and 1.5U_eq for the CH₃ H atoms.

Computing details

For both compounds, data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The C10H21(C6H4)–NC and –CN molecules. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. The packing of (I); that of (II) is essentially the same. Left: view along a; right: view along b.
	Fig. 3. A view normal to the plane of the C6 ring in the molecule of (I). Only atoms C7 in the decyl side chains are shown.

(I) p-decylphenyl isocyanide

Crystal data

C17H25N	F(000) = 268
Mr = 243.38	Dx = 1.074 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 985 reflections
a = 4.6642 (12) Å	θ = 2.6–27.4°
b = 7.831 (2) Å	µ = 0.06 mm^−1
c = 20.607 (5) Å	T = 173 K
β = 91.13 (1)°	Plate, colorless
V = 752.5 (3) Å^3	0.50 × 0.25 × 0.10 mm
Z = 2

Data collection

Siemens SMART area-detector diffractometer	1827 independent reflections
Radiation source: fine-focus sealed tube	1190 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan SADABS; Sheldrick, 2002; Blessing, 1995	h = −6→6
Tmin = 0.83, Tmax = 0.99	k = −10→10
6459 measured reflections	l = −26→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.054P)^2 + 0.023P] where P = (Fo^2 + 2Fc^2)/3'
1827 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0163 (4)	0.2500	1.03516 (8)	0.0444 (4)
N2	0.1757 (3)	0.2500	0.99256 (6)	0.0348 (3)
C3	0.3717 (3)	0.2500	0.94150 (6)	0.0301 (4)
C4	0.4675 (2)	0.40436 (15)	0.91720 (5)	0.0333 (3)
H4	0.394 (2)	0.5105 (15)	0.9357 (4)	0.034 (3)*
C5	0.6616 (2)	0.40270 (15)	0.86747 (5)	0.0326 (3)
H5	0.727 (2)	0.5103 (16)	0.8499 (5)	0.039 (3)*
C6	0.7598 (3)	0.2500	0.84119 (6)	0.0300 (4)
C7	0.9508 (3)	0.2500	0.78310 (7)	0.0343 (4)
H7	1.076 (2)	0.3521 (14)	0.7848 (5)	0.039 (3)*
C8	0.7741 (3)	0.2500	0.71951 (7)	0.0313 (4)
H8	0.646 (2)	0.3515 (14)	0.7196 (5)	0.037 (3)*
C9	0.9539 (3)	0.2500	0.65875 (7)	0.0311 (4)
H9	1.084 (2)	0.3516 (14)	0.6590 (5)	0.037 (3)*
C10	0.7736 (3)	0.2500	0.59617 (7)	0.0324 (4)
H10	0.643 (2)	0.3508 (15)	0.5956 (5)	0.040 (3)*
C11	0.9507 (3)	0.2500	0.53483 (7)	0.0322 (4)
H11	1.082 (2)	0.3521 (14)	0.5353 (5)	0.039 (3)*
C12	0.7700 (3)	0.2500	0.47233 (7)	0.0332 (4)
H12	0.642 (2)	0.3518 (15)	0.4721 (5)	0.041 (3)*
C13	0.9488 (3)	0.2500	0.41132 (7)	0.0322 (4)
H13	1.079 (2)	0.3508 (14)	0.4115 (5)	0.036 (3)*
C14	0.7697 (3)	0.2500	0.34850 (7)	0.0330 (4)
H14	0.638 (2)	0.3502 (14)	0.3480 (5)	0.038 (3)*
C15	0.9467 (3)	0.2500	0.28737 (7)	0.0346 (4)
H15	1.078 (2)	0.3515 (14)	0.2881 (5)	0.041 (3)*
C16	0.7633 (4)	0.2500	0.22568 (8)	0.0461 (5)
H16B	0.635 (3)	0.3539 (17)	0.2245 (6)	0.066 (4)*
H16A	0.881 (4)	0.2500	0.1867 (9)	0.053 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0453 (10)	0.0451 (10)	0.0430 (10)	0.000	0.0078 (8)	0.000
N2	0.0316 (7)	0.0402 (8)	0.0325 (7)	0.000	−0.0005 (6)	0.000
C3	0.0254 (8)	0.0399 (9)	0.0248 (8)	0.000	−0.0007 (6)	0.000
C4	0.0336 (6)	0.0349 (6)	0.0314 (6)	0.0033 (5)	−0.0010 (5)	−0.0020 (5)
C5	0.0321 (6)	0.0348 (6)	0.0308 (6)	−0.0021 (5)	−0.0023 (5)	0.0038 (5)
C6	0.0238 (8)	0.0404 (9)	0.0256 (8)	0.000	−0.0041 (6)	0.000
C7	0.0276 (9)	0.0456 (10)	0.0297 (8)	0.000	−0.0005 (7)	0.000
C8	0.0277 (9)	0.0383 (9)	0.0279 (8)	0.000	0.0009 (6)	0.000
C9	0.0275 (9)	0.0376 (9)	0.0282 (8)	0.000	0.0009 (6)	0.000
C10	0.0288 (9)	0.0392 (9)	0.0292 (8)	0.000	0.0019 (6)	0.000
C11	0.0290 (9)	0.0381 (9)	0.0294 (8)	0.000	0.0022 (6)	0.000
C12	0.0300 (9)	0.0397 (9)	0.0301 (9)	0.000	0.0021 (7)	0.000
C13	0.0278 (9)	0.0378 (9)	0.0310 (8)	0.000	0.0015 (6)	0.000
C14	0.0307 (9)	0.0368 (9)	0.0314 (8)	0.000	0.0011 (7)	0.000
C15	0.0345 (10)	0.0382 (9)	0.0311 (9)	0.000	0.0032 (7)	0.000
C16	0.0500 (12)	0.0585 (12)	0.0298 (10)	0.000	0.0006 (8)	0.000

Geometric parameters (Å, º)

C1—N2	1.1616 (18)	C9—H9	1.001 (11)
N2—C3	1.4072 (18)	C10—C11	1.523 (2)
C3—C4	1.3858 (13)	C10—H10	0.997 (11)
C3—C4^i	1.3858 (13)	C11—C12	1.5252 (19)
C4—C5	1.3808 (15)	C11—H11	1.007 (11)
C4—H4	0.979 (11)	C12—C13	1.523 (2)
C5—C6	1.3939 (13)	C12—H12	0.995 (11)
C5—H5	0.969 (12)	C13—C14	1.527 (2)
C6—C5^i	1.3939 (13)	C13—H13	0.995 (11)
C6—C7	1.506 (2)	C14—C15	1.520 (2)
C7—C8	1.5342 (19)	C14—H14	0.996 (11)
C7—H7	0.989 (11)	C15—C16	1.518 (2)
C8—C9	1.521 (2)	C15—H15	1.003 (11)
C8—H8	0.995 (11)	C16—H16B	1.009 (13)
C9—C10	1.5255 (19)	C16—H16A	0.979 (18)
C1—N2—C3	179.30 (15)	C12—C11—H11	109.5 (6)
C4—C3—C4^i	121.45 (14)	C13—C12—C11	113.25 (13)
C4—C3—N2	119.27 (7)	C13—C12—H12	109.5 (6)
C4^i—C3—N2	119.27 (7)	C11—C12—H12	108.9 (6)
C5—C4—C3	118.73 (11)	C12—C13—C14	113.61 (13)
C5—C4—H4	122.4 (6)	C12—C13—H13	109.9 (6)
C3—C4—H4	118.9 (6)	C14—C13—H13	109.1 (6)
C4—C5—C6	121.45 (12)	C15—C14—C13	113.93 (13)
C4—C5—H5	119.1 (6)	C15—C14—H14	109.6 (6)
C6—C5—H5	119.4 (6)	C13—C14—H14	109.6 (6)
C5^i—C6—C5	118.16 (14)	C16—C15—C14	112.83 (14)
C5^i—C6—C7	120.86 (7)	C16—C15—H15	110.3 (6)
C5—C6—C7	120.86 (7)	C14—C15—H15	109.2 (6)
C6—C7—C8	111.27 (12)	C15—C16—H16B	110.1 (7)
C6—C7—H7	109.2 (6)	C15—C16—H16A	111.8 (10)
C8—C7—H7	109.6 (6)	H7^i—C7—H7	107.8 (9)
C9—C8—C7	114.05 (12)	H8^i—C8—H8	106.1 (9)
C9—C8—H8	110.0 (6)	H9^i—C9—H9	105.3 (9)
C7—C8—H8	108.2 (6)	H10^i—C10—H10	104.7 (9)
C8—C9—C10	113.09 (12)	H11^i—C11—H11	105.2 (9)
C8—C9—H9	109.9 (6)	H12^i—C12—H12	106.5 (9)
C10—C9—H9	109.2 (6)	H13^i—C13—H13	104.9 (9)
C11—C10—C9	113.74 (13)	H14^i—C14—H14	104.0 (9)
C11—C10—H10	109.4 (6)	H15^i—C15—H15	104.8 (9)
C9—C10—H10	109.6 (6)	H16B^i—C16—H16B	107.4 (9)
C10—C11—C12	113.64 (13)	H16B—C16—H16A	108.6 (9)
C10—C11—H11	109.4 (6)

Symmetry code: (i) x, −y+1/2, z.

(II) p-decylbenzonitrile

Crystal data

C17H25N	F(000) = 268
Mr = 243.38	Dx = 1.088 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 1019 reflections
a = 4.6526 (12) Å	θ = 2.8–24.5°
b = 7.801 (2) Å	µ = 0.06 mm^−1
c = 20.466 (5) Å	T = 173 K
β = 90.50 (1)°	Plate, colorless
V = 742.8 (3) Å^3	0.40 × 0.20 × 0.07 mm
Z = 2

Data collection

Siemens SMART area-detector diffractometer	918 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.070
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
ω scans	h = −6→6
8715 measured reflections	k = −10→10
1812 independent reflections	l = −26→26

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.104P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.74	(Δ/σ)max = 0.001
1812 reflections	Δρmax = 0.22 e Å^−3
104 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.053 (7)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	−0.0006 (5)	0.2500	1.04131 (9)	0.0530 (6)
C2	0.1548 (5)	0.2500	0.99777 (11)	0.0400 (6)
C3	0.3533 (5)	0.2500	0.94377 (9)	0.0339 (6)
C4	0.4504 (3)	0.4039 (2)	0.91927 (6)	0.0387 (5)
H4A	0.3839	0.5093	0.9368	0.046*
C5	0.6463 (3)	0.4027 (2)	0.86865 (6)	0.0381 (5)
H5A	0.7144	0.5083	0.8516	0.046*
C6	0.7443 (4)	0.2500	0.84258 (9)	0.0329 (6)
C7	0.9381 (5)	0.2500	0.78401 (8)	0.0390 (6)
H7A	1.0630	0.1473	0.7854	0.047*	0.50
H7B	1.0630	0.3527	0.7854	0.047*	0.50
C8	0.7625 (5)	0.2500	0.72056 (8)	0.0368 (6)
H8A	0.6370	0.1475	0.7199	0.044*	0.50
H8B	0.6370	0.3525	0.7199	0.044*	0.50
C9	0.9458 (5)	0.2500	0.65944 (9)	0.0351 (6)
H9A	1.0712	0.3525	0.6600	0.042*	0.50
H9B	1.0712	0.1475	0.6600	0.042*	0.50
C10	0.7683 (5)	0.2500	0.59677 (9)	0.0375 (6)
H10A	0.6428	0.1475	0.5964	0.045*	0.50
H10B	0.6428	0.3525	0.5964	0.045*	0.50
C11	0.9478 (5)	0.2500	0.53518 (9)	0.0363 (6)
H11A	1.0733	0.1475	0.5355	0.044*	0.50
H11B	1.0733	0.3525	0.5355	0.044*	0.50
C12	0.7700 (5)	0.2500	0.47260 (9)	0.0373 (6)
H12A	0.6445	0.1475	0.4721	0.045*	0.50
H12B	0.6445	0.3525	0.4721	0.045*	0.50
C13	0.9527 (5)	0.2500	0.41105 (8)	0.0370 (6)
H13A	1.0781	0.3525	0.4115	0.044*	0.50
H13B	1.0781	0.1475	0.4115	0.044*	0.50
C14	0.7750 (5)	0.2500	0.34829 (8)	0.0361 (6)
H14A	0.6495	0.1475	0.3478	0.043*	0.50
H14B	0.6495	0.3525	0.3478	0.043*	0.50
C15	0.9561 (5)	0.2500	0.28701 (9)	0.0397 (6)
H15A	1.0814	0.1475	0.2873	0.048*	0.50
H15B	1.0814	0.3525	0.2873	0.048*	0.50
C16	0.7753 (5)	0.2500	0.22464 (9)	0.0520 (7)
H16A	0.9021	0.2500	0.1866	0.078*
H16B	0.6538	0.3526	0.2236	0.078*	0.50
H16C	0.6538	0.1474	0.2236	0.078*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0613 (15)	0.0579 (16)	0.0401 (12)	0.000	0.0138 (12)	0.000
C2	0.0386 (15)	0.0461 (17)	0.0354 (13)	0.000	−0.0020 (12)	0.000
C3	0.0331 (14)	0.0479 (17)	0.0208 (12)	0.000	−0.0004 (11)	0.000
C4	0.0452 (11)	0.0440 (12)	0.0270 (8)	−0.0007 (9)	−0.0004 (8)	−0.0019 (8)
C5	0.0430 (11)	0.0442 (12)	0.0270 (8)	−0.0021 (8)	−0.0005 (8)	0.0042 (8)
C6	0.0306 (14)	0.0427 (17)	0.0254 (12)	0.000	−0.0035 (11)	0.000
C7	0.0338 (15)	0.0562 (17)	0.0271 (12)	0.000	0.0013 (11)	0.000
C8	0.0371 (15)	0.0477 (16)	0.0256 (12)	0.000	0.0019 (11)	0.000
C9	0.0349 (14)	0.0425 (15)	0.0281 (12)	0.000	0.0027 (11)	0.000
C10	0.0374 (14)	0.0498 (17)	0.0255 (12)	0.000	0.0048 (11)	0.000
C11	0.0328 (14)	0.0468 (17)	0.0292 (12)	0.000	0.0039 (11)	0.000
C12	0.0363 (15)	0.0488 (16)	0.0268 (12)	0.000	0.0048 (11)	0.000
C13	0.0369 (14)	0.0473 (16)	0.0269 (12)	0.000	0.0032 (11)	0.000
C14	0.0346 (14)	0.0465 (16)	0.0274 (12)	0.000	0.0041 (11)	0.000
C15	0.0446 (15)	0.0447 (16)	0.0299 (13)	0.000	0.0025 (12)	0.000
C16	0.0593 (18)	0.067 (2)	0.0292 (13)	0.000	0.0001 (13)	0.000

Geometric parameters (Å, º)

N1—C2	1.153 (2)	C10—H10A	0.9900
C2—C3	1.446 (3)	C10—H10B	0.9900
C3—C4	1.3789 (17)	C11—C12	1.519 (2)
C3—C4^i	1.3789 (17)	C11—H11A	0.9900
C4—C5	1.3860 (19)	C11—H11B	0.9900
C4—H4A	0.9500	C12—C13	1.526 (2)
C5—C6	1.3842 (17)	C12—H12A	0.9900
C5—H5A	0.9500	C12—H12B	0.9900
C6—C5^i	1.3842 (17)	C13—C14	1.521 (3)
C6—C7	1.506 (3)	C13—H13A	0.9900
C7—C8	1.528 (3)	C13—H13B	0.9900
C7—H7A	0.9900	C14—C15	1.517 (2)
C7—H7B	0.9900	C14—H14A	0.9900
C8—C9	1.520 (2)	C14—H14B	0.9900
C8—H8A	0.9900	C15—C16	1.522 (3)
C8—H8B	0.9900	C15—H15A	0.9900
C9—C10	1.519 (3)	C15—H15B	0.9900
C9—H9A	0.9900	C16—H16A	0.9800
C9—H9B	0.9900	C16—H16B	0.9800
C10—C11	1.518 (2)	C16—H16C	0.9800
N1—C2—C3	179.2 (2)	C10—C11—C12	113.61 (17)
C4—C3—C4^i	121.1 (2)	C10—C11—H11A	108.8
C4—C3—C2	119.42 (10)	C12—C11—H11A	108.8
C4^i—C3—C2	119.42 (10)	C10—C11—H11B	108.8
C5—C4—C3	119.04 (17)	C12—C11—H11B	108.8
C5—C4—H4A	120.5	H11A—C11—H11B	107.7
C3—C4—H4A	120.5	C13—C12—C11	113.13 (17)
C4—C5—C6	121.00 (17)	C13—C12—H12A	109.0
C4—C5—H5A	119.5	C11—C12—H12A	109.0
C6—C5—H5A	119.5	C13—C12—H12B	109.0
C5^i—C6—C5	118.8 (2)	C11—C12—H12B	109.0
C5^i—C6—C7	120.54 (10)	H12A—C12—H12B	107.8
C5—C6—C7	120.54 (10)	C14—C13—C12	113.24 (18)
C6—C7—C8	110.93 (17)	C14—C13—H13A	108.9
C6—C7—H7A	109.5	C12—C13—H13A	108.9
C8—C7—H7A	109.5	C14—C13—H13B	108.9
C6—C7—H7B	109.5	C12—C13—H13B	108.9
C8—C7—H7B	109.5	H13A—C13—H13B	107.7
H7A—C7—H7B	108.0	C15—C14—C13	113.36 (17)
C9—C8—C7	113.55 (18)	C15—C14—H14A	108.9
C9—C8—H8A	108.9	C13—C14—H14A	108.9
C7—C8—H8A	108.9	C15—C14—H14B	108.9
C9—C8—H8B	108.9	C13—C14—H14B	108.9
C7—C8—H8B	108.9	H14A—C14—H14B	107.7
H8A—C8—H8B	107.7	C14—C15—C16	112.74 (18)
C10—C9—C8	112.94 (17)	C14—C15—H15A	109.0
C10—C9—H9A	109.0	C16—C15—H15A	109.0
C8—C9—H9A	109.0	C14—C15—H15B	109.0
C10—C9—H9B	109.0	C16—C15—H15B	109.0
C8—C9—H9B	109.0	H15A—C15—H15B	107.8
H9A—C9—H9B	107.8	C15—C16—H16A	109.5
C11—C10—C9	113.70 (17)	C15—C16—H16B	109.5
C11—C10—H10A	108.8	H16A—C16—H16B	109.5
C9—C10—H10A	108.8	C15—C16—H16C	109.5
C11—C10—H10B	108.8	H16A—C16—H16C	109.5
C9—C10—H10B	108.8	H16B—C16—H16C	109.5
H10A—C10—H10B	107.7

Symmetry code: (i) x, −y+1/2, z.