2-(1-Adamant-yl)-1-(3-amino-phen-yl)ethanol.

In the crystal structure of the title compound, C(18)H(25)NO, mol-ecules are linked via O-H⋯N hydrogen bonds, forming chains parallel to the c axis. Additional weak N-H⋯O inter-actions stabilize the crystal packing. The adamantane cage consists of three fused cyclo-hexane rings in almost ideal chair conformations, with C-C-C angles in the range 107.9 (10)-111.3 (11)°.

Related literature

For the biological activity of adamantane-bearing compounds, see: van der Schyf & Geldenhuys (2009) ▶. For related structures, see: Rouchal et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C18H25NO

M = 271.39

Orthorhombic,

a = 16.4467 (7) Å

b = 22.1873 (9) Å

c = 8.1033 (4) Å

V = 2957.0 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 120 K

0.30 × 0.20 × 0.10 mm

Data collection

Kuma KM-4 CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.984, T max = 1.000

30937 measured reflections

2602 independent reflections

1716 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.068

S = 0.85

2602 reflections

190 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 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 datablock(s) global, I. DOI: 10.1107/S1600536811034763/pk2344sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034763/pk2344Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034763/pk2344Isup3.cml

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

C18H25NO	Dx = 1.219 Mg m−3
Mr = 271.39	Melting point: 417 K
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 6715 reflections
a = 16.4467 (7) Å	θ = 2.9–27.3°
b = 22.1873 (9) Å	µ = 0.07 mm−1
c = 8.1033 (4) Å	T = 120 K
V = 2957.0 (2) Å3	Block, colourless
Z = 8	0.30 × 0.20 × 0.10 mm
F(000) = 1184

Kuma KM-4 CCD diffractometer	2602 independent reflections
Radiation source: fine-focus sealed tube	1716 reflections with I > 2σ(I)
graphite	Rint = 0.053
Detector resolution: 0.06 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −18→19
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −26→26
Tmin = 0.984, Tmax = 1.000	l = −8→9
30937 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ2(Fo2) + (0.0369P)2] where P = (Fo2 + 2Fc2)/3
2602 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.14 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
O1	0.36193 (5)	0.68130 (4)	0.21617 (11)	0.0266 (2)
H1A	0.3139	0.6810	0.2513	0.040*
N1	0.30745 (7)	0.68654 (6)	0.83127 (16)	0.0257 (3)
C1	0.54376 (8)	0.63700 (5)	0.11634 (15)	0.0185 (3)
C2	0.53840 (8)	0.57371 (6)	0.04034 (16)	0.0240 (3)
H2A	0.5560	0.5434	0.1227	0.029*
H2B	0.4813	0.5649	0.0102	0.029*
C3	0.59193 (8)	0.56895 (6)	−0.11291 (17)	0.0271 (4)
H3	0.5875	0.5274	−0.1599	0.033*
C4	0.68033 (8)	0.58181 (6)	−0.06886 (18)	0.0290 (4)
H4A	0.6998	0.5519	0.0127	0.035*
H4B	0.7147	0.5785	−0.1688	0.035*
C5	0.68711 (8)	0.64514 (6)	0.00313 (17)	0.0258 (3)
H5	0.7450	0.6536	0.0332	0.031*
C6	0.65776 (8)	0.69158 (6)	−0.12231 (18)	0.0281 (4)
H6A	0.6923	0.6900	−0.2222	0.034*
H6B	0.6619	0.7326	−0.0746	0.034*
C7	0.56932 (8)	0.67818 (6)	−0.16850 (17)	0.0254 (3)
H7	0.5503	0.7082	−0.2519	0.030*
C8	0.51604 (8)	0.68229 (6)	−0.01404 (15)	0.0228 (3)
H8A	0.5191	0.7236	0.0319	0.027*
H8B	0.4587	0.6741	−0.0440	0.027*
C9	0.56360 (8)	0.61470 (6)	−0.24141 (16)	0.0282 (4)
H9A	0.5067	0.6060	−0.2737	0.034*
H9B	0.5981	0.6118	−0.3412	0.034*
C10	0.63360 (8)	0.64953 (6)	0.15736 (17)	0.0242 (3)
H10A	0.6387	0.6904	0.2056	0.029*
H10B	0.6527	0.6201	0.2405	0.029*
C11	0.49559 (8)	0.64112 (6)	0.27851 (16)	0.0226 (3)
H11A	0.5205	0.6125	0.3574	0.027*
H11B	0.5039	0.6821	0.3238	0.027*
C12	0.40426 (8)	0.62906 (6)	0.27706 (16)	0.0221 (3)
H12	0.3932	0.5945	0.2009	0.027*
C13	0.37566 (8)	0.61198 (6)	0.44839 (16)	0.0197 (3)
C14	0.35838 (7)	0.65598 (6)	0.56444 (16)	0.0199 (3)
H14	0.3645	0.6972	0.5356	0.024*
C15	0.33224 (7)	0.64093 (6)	0.72247 (17)	0.0209 (3)
C16	0.32485 (8)	0.58040 (6)	0.76474 (17)	0.0250 (3)
H16	0.3071	0.5694	0.8721	0.030*
C17	0.34335 (8)	0.53647 (6)	0.65039 (18)	0.0277 (4)
H17	0.3390	0.4952	0.6804	0.033*
C18	0.36811 (8)	0.55162 (6)	0.49282 (17)	0.0259 (3)
H18	0.3800	0.5209	0.4149	0.031*
H1B	0.3144 (9)	0.6768 (6)	0.942 (2)	0.045 (5)*
H1C	0.3315 (8)	0.7235 (7)	0.8081 (17)	0.033 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0216 (5)	0.0341 (5)	0.0241 (6)	0.0052 (4)	0.0027 (5)	0.0062 (5)
N1	0.0280 (7)	0.0324 (8)	0.0166 (8)	0.0026 (6)	0.0010 (6)	0.0003 (6)
C1	0.0189 (8)	0.0208 (7)	0.0158 (8)	0.0003 (6)	0.0010 (6)	−0.0002 (6)
C2	0.0250 (8)	0.0223 (7)	0.0247 (8)	−0.0017 (6)	0.0019 (6)	0.0005 (6)
C3	0.0303 (8)	0.0224 (7)	0.0286 (9)	−0.0005 (6)	0.0046 (7)	−0.0073 (7)
C4	0.0272 (9)	0.0322 (8)	0.0276 (9)	0.0082 (6)	0.0086 (7)	0.0036 (7)
C5	0.0160 (7)	0.0359 (8)	0.0257 (9)	−0.0040 (6)	−0.0009 (6)	0.0016 (7)
C6	0.0296 (9)	0.0280 (8)	0.0268 (9)	−0.0056 (6)	0.0071 (7)	0.0018 (7)
C7	0.0270 (8)	0.0281 (8)	0.0210 (8)	0.0034 (6)	0.0015 (6)	0.0073 (7)
C8	0.0212 (7)	0.0241 (7)	0.0230 (8)	0.0027 (6)	−0.0003 (6)	0.0011 (6)
C9	0.0255 (8)	0.0403 (9)	0.0188 (8)	−0.0011 (7)	0.0026 (7)	−0.0045 (7)
C10	0.0239 (8)	0.0267 (8)	0.0221 (8)	0.0004 (6)	−0.0040 (7)	0.0005 (6)
C11	0.0252 (8)	0.0241 (7)	0.0185 (8)	−0.0008 (6)	−0.0023 (6)	0.0001 (6)
C12	0.0229 (8)	0.0232 (7)	0.0202 (8)	0.0023 (6)	0.0005 (7)	−0.0006 (6)
C13	0.0157 (7)	0.0256 (7)	0.0177 (8)	−0.0003 (6)	−0.0007 (6)	0.0008 (6)
C14	0.0174 (7)	0.0217 (7)	0.0206 (8)	−0.0004 (6)	−0.0006 (6)	0.0044 (6)
C15	0.0153 (7)	0.0291 (8)	0.0182 (8)	0.0010 (6)	−0.0018 (6)	0.0001 (6)
C16	0.0214 (8)	0.0331 (8)	0.0205 (9)	−0.0026 (6)	0.0009 (6)	0.0081 (7)
C17	0.0279 (9)	0.0239 (8)	0.0315 (10)	−0.0037 (6)	−0.0023 (7)	0.0070 (7)
C18	0.0277 (8)	0.0244 (7)	0.0255 (9)	0.0005 (6)	−0.0004 (7)	−0.0022 (7)

O1—C12	1.4393 (14)	C7—C9	1.5302 (18)
O1—H1A	0.8400	C7—C8	1.5305 (17)
N1—C15	1.4027 (17)	C7—H7	1.0000
N1—H1C	0.930 (14)	C8—H8A	0.9900
N1—H1B	0.934 (16)	C8—H8B	0.9900
C1—C8	1.5277 (16)	C9—H9A	0.9900
C1—C2	1.5360 (16)	C9—H9B	0.9900
C1—C11	1.5373 (17)	C10—H10A	0.9900
C1—C10	1.5397 (18)	C10—H10B	0.9900
C2—C3	1.5258 (17)	C11—C12	1.5257 (18)
C2—H2A	0.9900	C11—H11A	0.9900
C2—H2B	0.9900	C11—H11B	0.9900
C3—C4	1.5240 (18)	C12—C13	1.5141 (17)
C3—C9	1.5271 (18)	C12—H12	1.0000
C3—H3	1.0000	C13—C14	1.3850 (17)
C4—C5	1.5254 (18)	C13—C18	1.3923 (17)
C4—H4A	0.9900	C14—C15	1.3915 (18)
C4—H4B	0.9900	C14—H14	0.9500
C5—C6	1.5258 (18)	C15—C16	1.3912 (17)
C5—C10	1.5317 (18)	C16—C17	1.3789 (19)
C5—H5	1.0000	C16—H16	0.9500
C6—C7	1.5311 (18)	C17—C18	1.3817 (18)
C6—H6A	0.9900	C17—H17	0.9500
C6—H6B	0.9900	C18—H18	0.9500
C12—O1—H1A	109.5	C1—C8—H8A	109.5
C15—N1—H1C	112.7 (9)	C7—C8—H8A	109.5
C15—N1—H1B	113.8 (9)	C1—C8—H8B	109.5
H1C—N1—H1B	110.3 (13)	C7—C8—H8B	109.5
C8—C1—C2	107.88 (10)	H8A—C8—H8B	108.1
C8—C1—C11	113.47 (10)	C3—C9—C7	109.26 (11)
C2—C1—C11	111.57 (10)	C3—C9—H9A	109.8
C8—C1—C10	108.48 (10)	C7—C9—H9A	109.8
C2—C1—C10	107.86 (10)	C3—C9—H9B	109.8
C11—C1—C10	107.42 (10)	C7—C9—H9B	109.8
C3—C2—C1	110.89 (10)	H9A—C9—H9B	108.3
C3—C2—H2A	109.5	C5—C10—C1	111.33 (11)
C1—C2—H2A	109.5	C5—C10—H10A	109.4
C3—C2—H2B	109.5	C1—C10—H10A	109.4
C1—C2—H2B	109.5	C5—C10—H10B	109.4
H2A—C2—H2B	108.1	C1—C10—H10B	109.4
C2—C3—C4	110.29 (11)	H10A—C10—H10B	108.0
C2—C3—C9	109.45 (11)	C12—C11—C1	119.36 (11)
C4—C3—C9	109.04 (11)	C12—C11—H11A	107.5
C2—C3—H3	109.3	C1—C11—H11A	107.5
C4—C3—H3	109.3	C12—C11—H11B	107.5
C9—C3—H3	109.3	C1—C11—H11B	107.5
C5—C4—C3	109.38 (11)	H11A—C11—H11B	107.0
C5—C4—H4A	109.8	O1—C12—C13	111.45 (10)
C3—C4—H4A	109.8	O1—C12—C11	109.72 (10)
C5—C4—H4B	109.8	C13—C12—C11	110.04 (11)
C3—C4—H4B	109.8	O1—C12—H12	108.5
H4A—C4—H4B	108.2	C13—C12—H12	108.5
C6—C5—C4	110.13 (11)	C11—C12—H12	108.5
C6—C5—C10	108.59 (11)	C14—C13—C18	118.96 (12)
C4—C5—C10	109.19 (11)	C14—C13—C12	120.66 (11)
C6—C5—H5	109.6	C18—C13—C12	120.37 (12)
C4—C5—H5	109.6	C13—C14—C15	121.27 (12)
C10—C5—H5	109.6	C13—C14—H14	119.4
C5—C6—C7	109.41 (11)	C15—C14—H14	119.4
C5—C6—H6A	109.8	C14—C15—C16	119.03 (12)
C7—C6—H6A	109.8	C14—C15—N1	119.67 (12)
C5—C6—H6B	109.8	C16—C15—N1	121.08 (13)
C7—C6—H6B	109.8	C17—C16—C15	119.84 (13)
H6A—C6—H6B	108.2	C17—C16—H16	120.1
C6—C7—C9	109.36 (11)	C15—C16—H16	120.1
C6—C7—C8	109.41 (11)	C16—C17—C18	120.94 (13)
C9—C7—C8	109.60 (10)	C16—C17—H17	119.5
C6—C7—H7	109.5	C18—C17—H17	119.5
C9—C7—H7	109.5	C17—C18—C13	119.95 (13)
C8—C7—H7	109.5	C17—C18—H18	120.0
C1—C8—C7	110.82 (10)	C13—C18—H18	120.0

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1i	0.84	2.10	2.9400 (14)	176.
N1—H1C···O1ii	0.930 (15)	2.295 (15)	3.2048 (16)	166.0 (13)
N1—H1B···O1iii	0.930 (16)	2.357 (16)	3.2472 (16)	160.1 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.84	2.10	2.9400 (14)	176
N1—H1C⋯O1ii	0.930 (15)	2.295 (15)	3.2048 (16)	166.0 (13)
N1—H1B⋯O1iii	0.930 (16)	2.357 (16)	3.2472 (16)	160.1 (14)

Symmetry codes: (i) ; (ii) ; (iii) .