1-(1-Adamantylmeth-yl)-1H-benzimidazole.

The asymmetric unit of the title compound, C(18)H(22)N(2), contains two independent mol-ecules which differ slightly with respect to the torsion angles involving the atoms joining the adamantyl and benzimidazole groups. The bond angles in the adamantane cage vary within the range 108.27 (9)-110.55 (10)°. The benzimidazole ring system in both mol-ecules is essentially planar, the maximum deviations from the best planes being 0.0134 (15) and 0.0229 (14) Å. In the crystal, weak C-H⋯π inter-actions link the molecules.

Related literature

For the synthesis, spectroscopic characterization and biological activity of the title compound, see: Hille et al. (2011 ▶). For background to C(sp 2)—H⋯π inter­actions, see: Takahashi et al. (2010 ▶). For two polymorphs of a related structure, see: Lei & Zhou (2009 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

C18H22N2

M = 266.38

Monoclinic,

a = 22.0249 (9) Å

b = 6.4628 (1) Å

c = 22.2739 (8) Å

β = 118.694 (5)°

V = 2781.2 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.928, T max = 1.000

32353 measured reflections

4899 independent reflections

3314 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.064

S = 0.83

4899 reflections

361 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041018/lh5341sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041018/lh5341Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041018/lh5341Isup3.cml

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

C18H22N2	F(000) = 1152
Mr = 266.38	Dx = 1.272 Mg m−3
Monoclinic, P21/n	Melting point: 486 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 22.0249 (9) Å	Cell parameters from 9351 reflections
b = 6.4628 (1) Å	θ = 2.8–27.3°
c = 22.2739 (8) Å	µ = 0.08 mm−1
β = 118.694 (5)°	T = 120 K
V = 2781.2 (2) Å3	Block, colourless
Z = 8	0.30 × 0.20 × 0.20 mm

Oxford Diffraction Xcalibur Sapphire2 diffractometer	4899 independent reflections
Radiation source: fine-focus sealed tube	3314 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 8.4353 pixels mm-1	θmax = 25.0°, θmin = 3.2°
ω scans	h = −26→17
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −7→7
Tmin = 0.928, Tmax = 1.000	l = −26→26
32353 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H-atom parameters constrained
S = 0.83	w = 1/[σ2(Fo2) + (0.0354P)2] where P = (Fo2 + 2Fc2)/3
4899 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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
N1	0.58857 (5)	0.07364 (14)	0.28113 (5)	0.0206 (2)
N2	0.55730 (5)	0.39787 (15)	0.24104 (5)	0.0258 (3)
C1	0.58788 (6)	0.27873 (18)	0.29503 (6)	0.0238 (3)
H1	0.6080	0.3312	0.3404	0.029*
C2	0.53553 (6)	0.26067 (18)	0.18631 (6)	0.0212 (3)
C3	0.49849 (6)	0.2979 (2)	0.11594 (6)	0.0272 (3)
H3	0.4847	0.4340	0.0986	0.033*
C4	0.48257 (7)	0.1313 (2)	0.07262 (6)	0.0297 (3)
H4	0.4574	0.1531	0.0246	0.036*
C5	0.50261 (6)	−0.0698 (2)	0.09772 (6)	0.0290 (3)
H5	0.4909	−0.1811	0.0662	0.035*
C6	0.53897 (6)	−0.11098 (19)	0.16698 (6)	0.0249 (3)
H6	0.5526	−0.2474	0.1840	0.030*
C7	0.55451 (6)	0.05820 (18)	0.21038 (6)	0.0201 (3)
C8	0.62286 (6)	−0.09207 (18)	0.33114 (6)	0.0221 (3)
H8A	0.6009	−0.2255	0.3100	0.026*
H8B	0.6150	−0.0687	0.3708	0.026*
C9	0.70077 (6)	−0.10925 (17)	0.35702 (5)	0.0170 (3)
C10	0.73908 (6)	0.08829 (17)	0.39375 (6)	0.0204 (3)
H10A	0.7223	0.2061	0.3614	0.025*
H10B	0.7293	0.1191	0.4318	0.025*
C11	0.81690 (6)	0.06242 (18)	0.42177 (6)	0.0227 (3)
H11	0.8412	0.1921	0.4458	0.027*
C12	0.83131 (7)	0.01928 (18)	0.36233 (6)	0.0248 (3)
H12A	0.8817	0.0039	0.3798	0.030*
H12B	0.8148	0.1368	0.3298	0.030*
C13	0.79412 (6)	−0.17918 (18)	0.32558 (6)	0.0222 (3)
H13	0.8035	−0.2068	0.2866	0.027*
C14	0.82057 (7)	−0.36073 (18)	0.37585 (6)	0.0255 (3)
H14A	0.8709	−0.3786	0.3934	0.031*
H14B	0.7970	−0.4899	0.3522	0.031*
C15	0.80601 (7)	−0.31763 (18)	0.43533 (6)	0.0239 (3)
H15	0.8231	−0.4360	0.4683	0.029*
C16	0.72824 (7)	−0.29034 (18)	0.40795 (6)	0.0229 (3)
H16A	0.7189	−0.2635	0.4465	0.027*
H16B	0.7039	−0.4192	0.3849	0.027*
C17	0.71637 (6)	−0.15487 (18)	0.29825 (6)	0.0210 (3)
H17A	0.6924	−0.2835	0.2746	0.025*
H17B	0.6988	−0.0403	0.2647	0.025*
C18	0.84322 (7)	−0.11922 (18)	0.47179 (6)	0.0276 (3)
H18A	0.8347	−0.0918	0.5108	0.033*
H18B	0.8937	−0.1356	0.4899	0.033*
N21	0.81236 (5)	0.11037 (14)	0.61146 (5)	0.0206 (2)
N22	0.77666 (6)	0.43222 (15)	0.57082 (5)	0.0266 (3)
C21	0.82934 (7)	0.31252 (19)	0.60867 (6)	0.0247 (3)
H21	0.8756	0.3621	0.6323	0.030*
C22	0.71997 (7)	0.29919 (18)	0.54557 (6)	0.0221 (3)
C23	0.65052 (7)	0.3378 (2)	0.50043 (6)	0.0276 (3)
H23	0.6351	0.4728	0.4828	0.033*
C24	0.60493 (7)	0.1751 (2)	0.48206 (6)	0.0297 (3)
H24	0.5572	0.1988	0.4516	0.036*
C25	0.62717 (7)	−0.0254 (2)	0.50718 (6)	0.0279 (3)
H25	0.5942	−0.1344	0.4931	0.033*
C26	0.69569 (7)	−0.06793 (19)	0.55175 (6)	0.0231 (3)
H26	0.7109	−0.2035	0.5689	0.028*
C27	0.74142 (7)	0.09792 (18)	0.57037 (6)	0.0202 (3)
C28	0.86030 (6)	−0.05658 (18)	0.65027 (6)	0.0211 (3)
H28A	0.9047	−0.0329	0.6503	0.025*
H28B	0.8411	−0.1891	0.6264	0.025*
C29	0.87474 (6)	−0.07727 (17)	0.72453 (6)	0.0170 (3)
C30	0.90524 (6)	0.12265 (17)	0.76505 (6)	0.0196 (3)
H30A	0.9475	0.1611	0.7625	0.023*
H30B	0.8713	0.2365	0.7447	0.023*
C31	0.92319 (6)	0.09273 (18)	0.83991 (6)	0.0214 (3)
H31	0.9433	0.2237	0.8658	0.026*
C32	0.97601 (6)	−0.08287 (18)	0.87178 (6)	0.0252 (3)
H32A	1.0189	−0.0479	0.8700	0.030*
H32B	0.9879	−0.1014	0.9203	0.030*
C33	0.94509 (7)	−0.28301 (18)	0.83216 (6)	0.0227 (3)
H33	0.9794	−0.3980	0.8528	0.027*
C34	0.87901 (7)	−0.33678 (18)	0.83533 (6)	0.0254 (3)
H34A	0.8592	−0.4672	0.8102	0.031*
H34B	0.8900	−0.3571	0.8835	0.031*
C35	0.82659 (6)	−0.16154 (18)	0.80349 (6)	0.0223 (3)
H35	0.7834	−0.1967	0.8056	0.027*
C36	0.80937 (6)	−0.13371 (18)	0.72869 (6)	0.0208 (3)
H36A	0.7895	−0.2636	0.7032	0.025*
H36B	0.7744	−0.0228	0.7074	0.025*
C37	0.92803 (6)	−0.25205 (17)	0.75754 (6)	0.0210 (3)
H37A	0.9092	−0.3821	0.7317	0.025*
H37B	0.9708	−0.2171	0.7556	0.025*
C38	0.85747 (7)	0.03925 (18)	0.84316 (6)	0.0239 (3)
H38A	0.8235	0.1531	0.8230	0.029*
H38B	0.8683	0.0217	0.8915	0.029*

	U11	U22	U33	U12	U13	U23
N1	0.0174 (6)	0.0193 (6)	0.0220 (5)	0.0012 (5)	0.0070 (5)	0.0012 (4)
N2	0.0240 (7)	0.0219 (6)	0.0326 (6)	0.0042 (5)	0.0145 (5)	0.0022 (5)
C1	0.0203 (8)	0.0231 (7)	0.0282 (7)	0.0005 (6)	0.0118 (6)	−0.0036 (6)
C2	0.0135 (8)	0.0227 (7)	0.0282 (7)	0.0014 (6)	0.0104 (6)	0.0035 (5)
C3	0.0192 (8)	0.0300 (7)	0.0336 (7)	0.0041 (6)	0.0136 (6)	0.0109 (6)
C4	0.0196 (8)	0.0416 (9)	0.0237 (7)	−0.0017 (7)	0.0070 (6)	0.0063 (6)
C5	0.0239 (9)	0.0330 (8)	0.0249 (7)	−0.0076 (7)	0.0077 (6)	−0.0033 (6)
C6	0.0218 (8)	0.0231 (7)	0.0263 (7)	−0.0038 (6)	0.0087 (6)	0.0005 (6)
C7	0.0124 (8)	0.0242 (7)	0.0221 (7)	−0.0016 (6)	0.0071 (6)	0.0025 (5)
C8	0.0247 (8)	0.0200 (7)	0.0218 (7)	−0.0003 (6)	0.0113 (6)	0.0023 (5)
C9	0.0177 (8)	0.0164 (6)	0.0163 (6)	0.0014 (5)	0.0076 (6)	0.0010 (5)
C10	0.0235 (8)	0.0178 (6)	0.0190 (6)	0.0025 (6)	0.0094 (6)	−0.0011 (5)
C11	0.0193 (8)	0.0190 (7)	0.0244 (7)	−0.0009 (6)	0.0063 (6)	−0.0052 (5)
C12	0.0216 (8)	0.0223 (7)	0.0315 (7)	0.0026 (6)	0.0134 (7)	0.0043 (6)
C13	0.0258 (9)	0.0226 (7)	0.0232 (6)	0.0017 (6)	0.0156 (6)	−0.0014 (5)
C14	0.0254 (8)	0.0194 (7)	0.0329 (7)	0.0030 (6)	0.0149 (7)	−0.0008 (6)
C15	0.0253 (9)	0.0221 (7)	0.0221 (7)	0.0077 (6)	0.0097 (6)	0.0075 (5)
C16	0.0303 (9)	0.0203 (7)	0.0207 (6)	0.0020 (6)	0.0143 (6)	0.0025 (5)
C17	0.0262 (8)	0.0186 (6)	0.0171 (6)	−0.0011 (6)	0.0095 (6)	−0.0013 (5)
C18	0.0235 (8)	0.0330 (8)	0.0199 (7)	0.0052 (6)	0.0053 (6)	−0.0007 (6)
N21	0.0234 (7)	0.0184 (6)	0.0190 (5)	0.0037 (5)	0.0094 (5)	0.0028 (4)
N22	0.0324 (7)	0.0223 (6)	0.0233 (6)	0.0043 (6)	0.0119 (5)	0.0039 (5)
C21	0.0309 (9)	0.0223 (7)	0.0222 (7)	−0.0010 (6)	0.0138 (6)	0.0012 (6)
C22	0.0292 (9)	0.0221 (7)	0.0160 (6)	0.0058 (6)	0.0116 (6)	0.0011 (5)
C23	0.0354 (9)	0.0260 (7)	0.0185 (7)	0.0111 (7)	0.0108 (7)	0.0020 (6)
C24	0.0256 (9)	0.0367 (8)	0.0196 (7)	0.0097 (7)	0.0051 (6)	−0.0019 (6)
C25	0.0279 (9)	0.0321 (8)	0.0200 (7)	−0.0007 (7)	0.0085 (7)	−0.0054 (6)
C26	0.0280 (9)	0.0216 (7)	0.0176 (6)	0.0041 (6)	0.0093 (6)	−0.0005 (5)
C27	0.0224 (8)	0.0246 (7)	0.0131 (6)	0.0036 (6)	0.0083 (6)	−0.0016 (5)
C28	0.0205 (8)	0.0196 (6)	0.0229 (7)	0.0045 (6)	0.0102 (6)	0.0017 (5)
C29	0.0155 (7)	0.0163 (6)	0.0196 (6)	0.0009 (5)	0.0087 (6)	0.0015 (5)
C30	0.0160 (8)	0.0179 (6)	0.0258 (7)	0.0003 (5)	0.0108 (6)	0.0018 (5)
C31	0.0214 (8)	0.0181 (6)	0.0210 (6)	−0.0016 (6)	0.0074 (6)	−0.0019 (5)
C32	0.0221 (8)	0.0274 (7)	0.0221 (7)	0.0012 (6)	0.0073 (6)	0.0026 (6)
C33	0.0224 (8)	0.0193 (6)	0.0230 (7)	0.0060 (6)	0.0084 (6)	0.0053 (5)
C34	0.0348 (9)	0.0197 (7)	0.0235 (7)	−0.0012 (6)	0.0154 (6)	0.0027 (5)
C35	0.0206 (8)	0.0233 (7)	0.0264 (7)	−0.0019 (6)	0.0140 (6)	0.0014 (5)
C36	0.0183 (8)	0.0193 (6)	0.0238 (6)	−0.0002 (6)	0.0094 (6)	−0.0006 (5)
C37	0.0199 (8)	0.0184 (6)	0.0256 (7)	0.0014 (6)	0.0117 (6)	0.0003 (5)
C38	0.0284 (9)	0.0237 (7)	0.0220 (7)	0.0033 (6)	0.0141 (6)	0.0019 (5)

N1—C1	1.3629 (14)	N21—C21	1.3685 (14)
N1—C7	1.3860 (14)	N21—C27	1.3829 (15)
N1—C8	1.4664 (13)	N21—C28	1.4661 (14)
N2—C1	1.3096 (14)	N22—C21	1.3100 (15)
N2—C2	1.3931 (15)	N22—C22	1.3929 (15)
C1—H1	0.9500	C21—H21	0.9500
C2—C3	1.3972 (16)	C22—C23	1.3915 (17)
C2—C7	1.3997 (16)	C22—C27	1.4035 (16)
C3—C4	1.3744 (17)	C23—C24	1.3738 (18)
C3—H3	0.9500	C23—H23	0.9500
C4—C5	1.4000 (17)	C24—C25	1.4029 (17)
C4—H4	0.9500	C24—H24	0.9500
C5—C6	1.3805 (16)	C25—C26	1.3784 (17)
C5—H5	0.9500	C25—H25	0.9500
C6—C7	1.3889 (16)	C26—C27	1.3908 (16)
C6—H6	0.9500	C26—H26	0.9500
C8—C9	1.5294 (16)	C28—C29	1.5329 (15)
C8—H8A	0.9900	C28—H28A	0.9900
C8—H8B	0.9900	C28—H28B	0.9900
C9—C10	1.5324 (15)	C29—C36	1.5306 (16)
C9—C17	1.5331 (15)	C29—C30	1.5340 (15)
C9—C16	1.5374 (15)	C29—C37	1.5380 (15)
C10—C11	1.5257 (16)	C30—C31	1.5299 (15)
C10—H10A	0.9900	C30—H30A	0.9900
C10—H10B	0.9900	C30—H30B	0.9900
C11—C12	1.5280 (16)	C31—C38	1.5234 (17)
C11—C18	1.5281 (16)	C31—C32	1.5337 (15)
C11—H11	1.0000	C31—H31	1.0000
C12—C13	1.5304 (16)	C32—C33	1.5292 (16)
C12—H12A	0.9900	C32—H32A	0.9900
C12—H12B	0.9900	C32—H32B	0.9900
C13—C17	1.5253 (16)	C33—C34	1.5305 (17)
C13—C14	1.5308 (16)	C33—C37	1.5310 (15)
C13—H13	1.0000	C33—H33	1.0000
C14—C15	1.5308 (16)	C34—C35	1.5273 (16)
C14—H14A	0.9900	C34—H34A	0.9900
C14—H14B	0.9900	C34—H34B	0.9900
C15—C16	1.5277 (16)	C35—C36	1.5314 (16)
C15—C18	1.5285 (16)	C35—C38	1.5331 (16)
C15—H15	1.0000	C35—H35	1.0000
C16—H16A	0.9900	C36—H36A	0.9900
C16—H16B	0.9900	C36—H36B	0.9900
C17—H17A	0.9900	C37—H37A	0.9900
C17—H17B	0.9900	C37—H37B	0.9900
C18—H18A	0.9900	C38—H38A	0.9900
C18—H18B	0.9900	C38—H38B	0.9900
C1—N1—C7	105.63 (10)	C21—N21—C27	105.78 (10)
C1—N1—C8	126.55 (10)	C21—N21—C28	126.46 (11)
C7—N1—C8	127.68 (10)	C27—N21—C28	127.76 (10)
C1—N2—C2	103.80 (10)	C21—N22—C22	103.92 (10)
N2—C1—N1	114.83 (11)	N22—C21—N21	114.59 (12)
N2—C1—H1	122.6	N22—C21—H21	122.7
N1—C1—H1	122.6	N21—C21—H21	122.7
N2—C2—C3	129.95 (11)	C23—C22—N22	129.96 (11)
N2—C2—C7	110.23 (10)	C23—C22—C27	119.75 (12)
C3—C2—C7	119.79 (11)	N22—C22—C27	110.24 (11)
C4—C3—C2	117.86 (12)	C24—C23—C22	118.07 (12)
C4—C3—H3	121.1	C24—C23—H23	121.0
C2—C3—H3	121.1	C22—C23—H23	121.0
C3—C4—C5	121.46 (12)	C23—C24—C25	121.53 (12)
C3—C4—H4	119.3	C23—C24—H24	119.2
C5—C4—H4	119.3	C25—C24—H24	119.2
C6—C5—C4	121.84 (12)	C26—C25—C24	121.56 (13)
C6—C5—H5	119.1	C26—C25—H25	119.2
C4—C5—H5	119.1	C24—C25—H25	119.2
C5—C6—C7	116.30 (12)	C25—C26—C27	116.53 (12)
C5—C6—H6	121.9	C25—C26—H26	121.7
C7—C6—H6	121.9	C27—C26—H26	121.7
N1—C7—C6	131.75 (11)	N21—C27—C26	131.96 (11)
N1—C7—C2	105.50 (10)	N21—C27—C22	105.45 (11)
C6—C7—C2	122.74 (11)	C26—C27—C22	122.55 (12)
N1—C8—C9	114.51 (9)	N21—C28—C29	114.71 (9)
N1—C8—H8A	108.6	N21—C28—H28A	108.6
C9—C8—H8A	108.6	C29—C28—H28A	108.6
N1—C8—H8B	108.6	N21—C28—H28B	108.6
C9—C8—H8B	108.6	C29—C28—H28B	108.6
H8A—C8—H8B	107.6	H28A—C28—H28B	107.6
C8—C9—C10	111.79 (9)	C36—C29—C28	111.85 (9)
C8—C9—C17	111.28 (9)	C36—C29—C30	108.90 (9)
C10—C9—C17	108.93 (9)	C28—C29—C30	111.52 (9)
C8—C9—C16	107.83 (9)	C36—C29—C37	108.67 (9)
C10—C9—C16	108.64 (9)	C28—C29—C37	107.17 (9)
C17—C9—C16	108.27 (9)	C30—C29—C37	108.62 (9)
C11—C10—C9	110.46 (9)	C31—C30—C29	110.23 (9)
C11—C10—H10A	109.6	C31—C30—H30A	109.6
C9—C10—H10A	109.6	C29—C30—H30A	109.6
C11—C10—H10B	109.6	C31—C30—H30B	109.6
C9—C10—H10B	109.6	C29—C30—H30B	109.6
H10A—C10—H10B	108.1	H30A—C30—H30B	108.1
C10—C11—C12	108.99 (10)	C38—C31—C30	109.04 (9)
C10—C11—C18	109.93 (10)	C38—C31—C32	109.70 (10)
C12—C11—C18	109.12 (10)	C30—C31—C32	109.85 (10)
C10—C11—H11	109.6	C38—C31—H31	109.4
C12—C11—H11	109.6	C30—C31—H31	109.4
C18—C11—H11	109.6	C32—C31—H31	109.4
C11—C12—C13	109.63 (10)	C33—C32—C31	109.28 (10)
C11—C12—H12A	109.7	C33—C32—H32A	109.8
C13—C12—H12A	109.7	C31—C32—H32A	109.8
C11—C12—H12B	109.7	C33—C32—H32B	109.8
C13—C12—H12B	109.7	C31—C32—H32B	109.8
H12A—C12—H12B	108.2	H32A—C32—H32B	108.3
C17—C13—C12	109.70 (10)	C32—C33—C34	109.59 (10)
C17—C13—C14	109.32 (10)	C32—C33—C37	108.97 (9)
C12—C13—C14	109.46 (10)	C34—C33—C37	109.67 (10)
C17—C13—H13	109.4	C32—C33—H33	109.5
C12—C13—H13	109.4	C34—C33—H33	109.5
C14—C13—H13	109.4	C37—C33—H33	109.5
C13—C14—C15	109.23 (10)	C35—C34—C33	109.50 (10)
C13—C14—H14A	109.8	C35—C34—H34A	109.8
C15—C14—H14A	109.8	C33—C34—H34A	109.8
C13—C14—H14B	109.8	C35—C34—H34B	109.8
C15—C14—H14B	109.8	C33—C34—H34B	109.8
H14A—C14—H14B	108.3	H34A—C34—H34B	108.2
C16—C15—C18	109.12 (10)	C34—C35—C36	109.23 (10)
C16—C15—C14	109.64 (10)	C34—C35—C38	109.44 (10)
C18—C15—C14	109.32 (10)	C36—C35—C38	109.71 (9)
C16—C15—H15	109.6	C34—C35—H35	109.5
C18—C15—H15	109.6	C36—C35—H35	109.5
C14—C15—H15	109.6	C38—C35—H35	109.5
C15—C16—C9	110.55 (10)	C29—C36—C35	110.19 (10)
C15—C16—H16A	109.5	C29—C36—H36A	109.6
C9—C16—H16A	109.5	C35—C36—H36A	109.6
C15—C16—H16B	109.5	C29—C36—H36B	109.6
C9—C16—H16B	109.5	C35—C36—H36B	109.6
H16A—C16—H16B	108.1	H36A—C36—H36B	108.1
C13—C17—C9	110.37 (9)	C33—C37—C29	110.37 (9)
C13—C17—H17A	109.6	C33—C37—H37A	109.6
C9—C17—H17A	109.6	C29—C37—H37A	109.6
C13—C17—H17B	109.6	C33—C37—H37B	109.6
C9—C17—H17B	109.6	C29—C37—H37B	109.6
H17A—C17—H17B	108.1	H37A—C37—H37B	108.1
C11—C18—C15	109.76 (10)	C31—C38—C35	109.47 (10)
C11—C18—H18A	109.7	C31—C38—H38A	109.8
C15—C18—H18A	109.7	C35—C38—H38A	109.8
C11—C18—H18B	109.7	C31—C38—H38B	109.8
C15—C18—H18B	109.7	C35—C38—H38B	109.8
H18A—C18—H18B	108.2	H38A—C38—H38B	108.2

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg1i	0.95	3.07	3.9197 (16)	150.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cg1i	0.95	3.07	3.9197 (16)	150

Symmetry code: (i) .