1-(2-Phenyl-eth-yl)adamantane.

In the title compound, C(18)H(24), the adamantane cage consists of three fused cyclo-hexane rings in almost ideal chair conformations, with C-C-C angles in the range 108.0 (14)-111.1 (15)°. The phenyl and 1-adamantyl substituents adopt anti orientations with a C-C-C-C torsion angle of 177.10 (16)°. In the crystal packing, the mol-ecules are linked by weak C-H⋯π inter-actions into chains along the a axis.

Related literature

The title compound was prepared according to a modified procedure of Adkins & Billica (1948 ▶). For some important properties of compounds bearing the adamantane scaffold, see: van der Schyf et al. (2009 ▶); van Bommel et al. (2001 ▶). For a related structure, see: Raine et al. (2002 ▶).

Experimental

Crystal data

C18H24

M = 240.37

Orthorhombic,

a = 6.4844 (5) Å

b = 7.5109 (5) Å

c = 28.5305 (19) Å

V = 1389.55 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.06 mm−1

T = 120 K

0.40 × 0.20 × 0.20 mm

Data collection

Kuma KM-4-CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.924, T max = 1.000

11994 measured reflections

1452 independent reflections

1277 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.127

S = 1.30

1452 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.15 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 datablocks global, I. DOI: 10.1107/S1600536810023251/ez2215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023251/ez2215Isup2.hkl

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

C18H24	Dx = 1.149 Mg m−3
Mr = 240.37	Melting point: 321 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5446 reflections
a = 6.4844 (5) Å	θ = 3.1–27.2°
b = 7.5109 (5) Å	µ = 0.06 mm−1
c = 28.5305 (19) Å	T = 120 K
V = 1389.55 (17) Å3	Block, colourless
Z = 4	0.40 × 0.20 × 0.20 mm
F(000) = 528

Kuma KM-4-CCD diffractometer	1452 independent reflections
Radiation source: fine-focus sealed tube	1277 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 0.06 mm pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scan	h = −5→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −8→8
Tmin = 0.924, Tmax = 1.000	l = −33→33
11994 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.30	w = 1/[σ2(Fo2) + (0.0705P)2 + 0.0787P] where P = (Fo2 + 2Fc2)/3
1452 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.15 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
C1	0.8116 (4)	0.4428 (3)	0.14870 (8)	0.0172 (6)
C2	0.6166 (4)	0.4772 (3)	0.17845 (9)	0.0207 (6)
H2A	0.6402	0.5812	0.1991	0.025*
H2B	0.4993	0.5052	0.1575	0.025*
C3	0.5633 (4)	0.3148 (3)	0.20840 (8)	0.0206 (6)
H3	0.4366	0.3400	0.2272	0.025*
C4	0.5236 (4)	0.1543 (3)	0.17589 (9)	0.0232 (6)
H4A	0.4887	0.0482	0.1949	0.028*
H4B	0.4059	0.1803	0.1549	0.028*
C5	0.7167 (4)	0.1176 (3)	0.14680 (8)	0.0212 (6)
H5	0.6913	0.0137	0.1257	0.025*
C6	0.8974 (4)	0.0749 (3)	0.17999 (9)	0.0222 (6)
H6A	0.8640	−0.0316	0.1990	0.027*
H6B	1.0230	0.0490	0.1615	0.027*
C7	0.9363 (4)	0.2344 (3)	0.21230 (8)	0.0195 (6)
H7	1.0545	0.2072	0.2337	0.023*
C8	0.9892 (4)	0.3977 (3)	0.18208 (8)	0.0182 (6)
H8A	1.0171	0.5010	0.2027	0.022*
H8B	1.1154	0.3731	0.1637	0.022*
C9	0.7437 (4)	0.2729 (4)	0.24146 (8)	0.0217 (6)
H9A	0.7693	0.3756	0.2624	0.026*
H9B	0.7097	0.1683	0.2611	0.026*
C10	0.7703 (4)	0.2808 (3)	0.11744 (9)	0.0208 (6)
H10A	0.6548	0.3076	0.0959	0.025*
H10B	0.8941	0.2554	0.0983	0.025*
C11	0.8577 (4)	0.6112 (3)	0.12008 (8)	0.0219 (6)
H11A	0.7359	0.6377	0.1004	0.026*
H11B	0.8750	0.7118	0.1421	0.026*
C12	1.0478 (5)	0.6040 (4)	0.08826 (9)	0.0283 (7)
H12A	1.1701	0.5727	0.1073	0.034*
H12B	1.0284	0.5092	0.0646	0.034*
C13	1.0866 (5)	0.7775 (4)	0.06375 (8)	0.0234 (6)
C14	1.2499 (5)	0.8876 (4)	0.07581 (8)	0.0302 (7)
H14	1.3389	0.8539	0.1007	0.036*
C15	1.2855 (5)	1.0453 (4)	0.05228 (9)	0.0349 (8)
H15	1.3969	1.1197	0.0615	0.042*
C16	1.1596 (5)	1.0957 (4)	0.01530 (9)	0.0317 (7)
H16	1.1860	1.2027	−0.0014	0.038*
C17	0.9961 (5)	0.9891 (4)	0.00311 (9)	0.0285 (7)
H17	0.9071	1.0238	−0.0217	0.034*
C18	0.9604 (5)	0.8312 (4)	0.02684 (9)	0.0275 (7)
H18	0.8477	0.7581	0.0178	0.033*

	U11	U22	U33	U12	U13	U23
C1	0.0173 (14)	0.0180 (13)	0.0163 (11)	−0.0001 (11)	0.0018 (10)	−0.0003 (10)
C2	0.0141 (13)	0.0236 (14)	0.0244 (13)	0.0037 (11)	0.0005 (12)	−0.0009 (11)
C3	0.0150 (14)	0.0257 (14)	0.0212 (12)	0.0006 (11)	0.0051 (11)	0.0004 (11)
C4	0.0187 (15)	0.0262 (14)	0.0247 (12)	−0.0028 (12)	−0.0013 (12)	0.0051 (11)
C5	0.0238 (15)	0.0188 (13)	0.0210 (12)	−0.0015 (12)	−0.0036 (11)	−0.0037 (11)
C6	0.0196 (14)	0.0202 (13)	0.0269 (13)	0.0012 (12)	0.0022 (12)	0.0028 (11)
C7	0.0157 (14)	0.0246 (14)	0.0184 (12)	0.0004 (12)	−0.0023 (11)	0.0037 (11)
C8	0.0155 (13)	0.0214 (13)	0.0177 (11)	−0.0004 (11)	0.0010 (11)	−0.0020 (11)
C9	0.0196 (15)	0.0278 (15)	0.0176 (11)	−0.0020 (13)	0.0016 (11)	0.0017 (10)
C10	0.0199 (15)	0.0237 (14)	0.0187 (11)	0.0010 (12)	−0.0007 (11)	−0.0012 (10)
C11	0.0216 (14)	0.0217 (14)	0.0223 (12)	0.0016 (12)	−0.0002 (12)	0.0007 (11)
C12	0.0275 (16)	0.0289 (15)	0.0284 (13)	0.0014 (14)	0.0050 (13)	0.0058 (12)
C13	0.0252 (16)	0.0248 (14)	0.0201 (12)	−0.0005 (12)	0.0029 (11)	0.0015 (11)
C14	0.0302 (16)	0.0415 (18)	0.0190 (12)	−0.0061 (15)	−0.0020 (12)	0.0030 (12)
C15	0.040 (2)	0.0352 (17)	0.0291 (14)	−0.0181 (15)	−0.0039 (14)	−0.0028 (13)
C16	0.0468 (19)	0.0250 (14)	0.0235 (13)	−0.0047 (15)	0.0047 (13)	0.0029 (12)
C17	0.0307 (17)	0.0317 (15)	0.0232 (13)	0.0030 (14)	−0.0002 (14)	0.0046 (11)
C18	0.0237 (16)	0.0283 (15)	0.0306 (14)	−0.0033 (13)	−0.0027 (12)	0.0000 (12)

C1—C10	1.532 (3)	C8—H8B	0.9900
C1—C8	1.532 (3)	C9—H9A	0.9900
C1—C11	1.535 (3)	C9—H9B	0.9900
C1—C2	1.544 (3)	C10—H10A	0.9900
C2—C3	1.529 (3)	C10—H10B	0.9900
C2—H2A	0.9900	C11—C12	1.532 (4)
C2—H2B	0.9900	C11—H11A	0.9900
C3—C9	1.535 (4)	C11—H11B	0.9900
C3—C4	1.542 (3)	C12—C13	1.500 (4)
C3—H3	1.0000	C12—H12A	0.9900
C4—C5	1.527 (4)	C12—H12B	0.9900
C4—H4A	0.9900	C13—C14	1.387 (4)
C4—H4B	0.9900	C13—C18	1.393 (4)
C5—C10	1.525 (3)	C14—C15	1.381 (4)
C5—C6	1.540 (4)	C14—H14	0.9500
C5—H5	1.0000	C15—C16	1.387 (4)
C6—C7	1.533 (3)	C15—H15	0.9500
C6—H6A	0.9900	C16—C17	1.373 (4)
C6—H6B	0.9900	C16—H16	0.9500
C7—C9	1.528 (4)	C17—C18	1.385 (4)
C7—C8	1.538 (3)	C17—H17	0.9500
C7—H7	1.0000	C18—H18	0.9500
C8—H8A	0.9900
C10—C1—C8	108.5 (2)	C1—C8—H8B	109.5
C10—C1—C11	112.24 (18)	C7—C8—H8B	109.5
C8—C1—C11	111.5 (2)	H8A—C8—H8B	108.0
C10—C1—C2	108.1 (2)	C7—C9—C3	109.08 (18)
C8—C1—C2	108.09 (18)	C7—C9—H9A	109.9
C11—C1—C2	108.3 (2)	C3—C9—H9A	109.9
C3—C2—C1	111.0 (2)	C7—C9—H9B	109.9
C3—C2—H2A	109.4	C3—C9—H9B	109.9
C1—C2—H2A	109.4	H9A—C9—H9B	108.3
C3—C2—H2B	109.4	C5—C10—C1	110.99 (19)
C1—C2—H2B	109.4	C5—C10—H10A	109.4
H2A—C2—H2B	108.0	C1—C10—H10A	109.4
C2—C3—C9	109.5 (2)	C5—C10—H10B	109.4
C2—C3—C4	108.97 (18)	C1—C10—H10B	109.4
C9—C3—C4	109.7 (2)	H10A—C10—H10B	108.0
C2—C3—H3	109.6	C12—C11—C1	116.3 (2)
C9—C3—H3	109.6	C12—C11—H11A	108.2
C4—C3—H3	109.6	C1—C11—H11A	108.2
C5—C4—C3	109.3 (2)	C12—C11—H11B	108.2
C5—C4—H4A	109.8	C1—C11—H11B	108.2
C3—C4—H4A	109.8	H11A—C11—H11B	107.4
C5—C4—H4B	109.8	C13—C12—C11	112.4 (2)
C3—C4—H4B	109.8	C13—C12—H12A	109.1
H4A—C4—H4B	108.3	C11—C12—H12A	109.1
C10—C5—C4	109.9 (2)	C13—C12—H12B	109.1
C10—C5—C6	109.4 (2)	C11—C12—H12B	109.1
C4—C5—C6	109.09 (18)	H12A—C12—H12B	107.9
C10—C5—H5	109.5	C14—C13—C18	117.6 (2)
C4—C5—H5	109.5	C14—C13—C12	122.0 (2)
C6—C5—H5	109.5	C18—C13—C12	120.4 (3)
C7—C6—C5	109.4 (2)	C15—C14—C13	121.2 (3)
C7—C6—H6A	109.8	C15—C14—H14	119.4
C5—C6—H6A	109.8	C13—C14—H14	119.4
C7—C6—H6B	109.8	C14—C15—C16	120.4 (3)
C5—C6—H6B	109.8	C14—C15—H15	119.8
H6A—C6—H6B	108.2	C16—C15—H15	119.8
C9—C7—C6	109.9 (2)	C17—C16—C15	119.2 (3)
C9—C7—C8	109.7 (2)	C17—C16—H16	120.4
C6—C7—C8	108.84 (18)	C15—C16—H16	120.4
C9—C7—H7	109.5	C16—C17—C18	120.3 (3)
C6—C7—H7	109.5	C16—C17—H17	119.9
C8—C7—H7	109.5	C18—C17—H17	119.9
C1—C8—C7	110.9 (2)	C17—C18—C13	121.3 (3)
C1—C8—H8A	109.5	C17—C18—H18	119.4
C7—C8—H8A	109.5	C13—C18—H18	119.4

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg1i	0.95	2.64	3.529 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯Cg1i	0.95	2.64	3.529 (3)	156

Symmetry code: (i) .