(1-Adamant-yl)(3-amino-phen-yl)methanone.

In the crystal sructure of the title compound, C(17)H(21)NO, the mol-ecular packing is stabilized by inter-molecular N-H⋯O hydrogen bonds and additional weak N-H⋯π inter-actions, forming chains that propagate along the b axis. Conjugation of the carbonyl group and the benzene ring is rather attenuated due to a twisting of the carbonyl group from the plane of the benzene ring [torsion angle = 27.1 (2)°].

Related literature

For recent reviews of the biological activity of some adamantane-bearing compounds, see: Ahrén (2009 ▶); Ginsberg (2010 ▶); Lagoja & De Clercq (2008 ▶). For the structures of similar adamantylated aromatic amines, see: Rouchal et al. (2009 ▶, 2011 ▶).

Experimental

Crystal data

C17H21NO

M = 255.35

Orthorhombic,

a = 6.4644 (1) Å

b = 8.1978 (3) Å

c = 25.1760 (5) Å

V = 1334.17 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.30 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.998, T max = 1.000

15931 measured reflections

1672 independent reflections

1531 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.073

S = 1.04

1672 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.17 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/S1600536811046009/pk2356sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046009/pk2356Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046009/pk2356Isup3.cml

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

C17H21NO	Dx = 1.271 Mg m−3
Mr = 255.35	Melting point: 372 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10578 reflections
a = 6.4644 (1) Å	θ = 3.2–27.2°
b = 8.1978 (3) Å	µ = 0.08 mm−1
c = 25.1760 (5) Å	T = 120 K
V = 1334.17 (6) Å3	Block, colourless
Z = 4	0.30 × 0.30 × 0.20 mm
F(000) = 552

Oxford Diffraction Xcalibur Sapphire2 diffractometer	1672 independent reflections
Radiation source: fine-focus sealed tube	1531 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 8.4353 pixels mm-1	θmax = 27.3°, θmin = 3.2°
ω scan	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −10→5
Tmin = 0.998, Tmax = 1.000	l = −32→32
15931 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) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0342P)2 + 0.3516P] where P = (Fo2 + 2Fc2)/3
1672 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.17 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	0.4200 (2)	0.29596 (16)	0.21048 (4)	0.0309 (3)
N1	0.1688 (3)	−0.2699 (2)	0.23832 (7)	0.0344 (4)
C1	0.3647 (2)	0.3819 (2)	0.12126 (6)	0.0170 (3)
C2	0.1811 (2)	0.5018 (2)	0.11371 (6)	0.0190 (3)
H2A	0.0525	0.4396	0.1069	0.023*
H2B	0.1613	0.5667	0.1465	0.023*
C3	0.2246 (2)	0.6165 (2)	0.06674 (6)	0.0214 (4)
H3	0.1048	0.6922	0.0619	0.026*
C4	0.2554 (3)	0.5155 (2)	0.01592 (6)	0.0220 (4)
H4A	0.1285	0.4522	0.0083	0.026*
H4B	0.2818	0.5892	−0.0145	0.026*
C5	0.4390 (2)	0.3989 (2)	0.02303 (6)	0.0202 (3)
H5	0.4585	0.3339	−0.0102	0.024*
C6	0.6351 (2)	0.4984 (2)	0.03404 (6)	0.0226 (4)
H6A	0.6638	0.5718	0.0037	0.027*
H6B	0.7547	0.4242	0.0385	0.027*
C7	0.6041 (3)	0.5995 (2)	0.08489 (6)	0.0213 (4)
H7	0.7323	0.6638	0.0923	0.026*
C8	0.5599 (2)	0.4852 (2)	0.13178 (6)	0.0204 (3)
H8A	0.5401	0.5504	0.1645	0.025*
H8B	0.6799	0.4121	0.1374	0.025*
C9	0.4214 (3)	0.7162 (2)	0.07774 (7)	0.0234 (4)
H9A	0.4488	0.7911	0.0477	0.028*
H9B	0.4028	0.7825	0.1103	0.028*
C10	0.3976 (3)	0.2828 (2)	0.06965 (6)	0.0184 (3)
H10A	0.5164	0.2078	0.0741	0.022*
H10B	0.2730	0.2164	0.0621	0.022*
C11	0.3283 (2)	0.2699 (2)	0.16894 (6)	0.0193 (3)
C12	0.1869 (2)	0.1237 (2)	0.16726 (6)	0.0190 (3)
C13	0.2376 (3)	−0.0037 (2)	0.20158 (6)	0.0215 (3)
H13	0.3620	0.0023	0.2216	0.026*
C14	0.1096 (3)	−0.1401 (2)	0.20729 (6)	0.0232 (4)
C15	−0.0785 (3)	−0.1424 (2)	0.17955 (6)	0.0252 (4)
H15	−0.1727	−0.2299	0.1847	0.030*
C16	−0.1272 (3)	−0.0174 (2)	0.14471 (6)	0.0246 (4)
H16	−0.2532	−0.0220	0.1254	0.030*
C17	0.0044 (3)	0.1143 (2)	0.13749 (6)	0.0217 (3)
H17	−0.0290	0.1973	0.1126	0.026*
H1A	0.068 (4)	−0.338 (3)	0.2494 (10)	0.058 (8)*
H1B	0.286 (4)	−0.257 (3)	0.2582 (9)	0.048 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0383 (7)	0.0326 (7)	0.0219 (6)	−0.0106 (7)	−0.0096 (6)	0.0026 (5)
N1	0.0409 (10)	0.0300 (9)	0.0324 (8)	−0.0094 (9)	−0.0087 (8)	0.0115 (8)
C1	0.0158 (7)	0.0174 (7)	0.0177 (7)	−0.0016 (7)	−0.0002 (6)	−0.0010 (7)
C2	0.0167 (7)	0.0182 (8)	0.0221 (7)	0.0007 (8)	0.0027 (6)	−0.0010 (7)
C3	0.0161 (8)	0.0194 (8)	0.0287 (8)	0.0030 (7)	0.0011 (6)	0.0047 (7)
C4	0.0187 (7)	0.0246 (9)	0.0226 (8)	−0.0025 (8)	−0.0022 (6)	0.0061 (7)
C5	0.0191 (8)	0.0233 (8)	0.0181 (7)	0.0000 (8)	0.0009 (6)	−0.0015 (7)
C6	0.0164 (7)	0.0259 (9)	0.0255 (8)	−0.0009 (8)	0.0035 (6)	0.0041 (7)
C7	0.0164 (7)	0.0220 (9)	0.0254 (8)	−0.0046 (8)	0.0003 (6)	0.0002 (7)
C8	0.0176 (7)	0.0222 (8)	0.0215 (7)	−0.0026 (8)	−0.0016 (6)	0.0000 (7)
C9	0.0235 (9)	0.0186 (8)	0.0283 (8)	−0.0039 (8)	0.0042 (7)	0.0017 (7)
C10	0.0183 (8)	0.0179 (8)	0.0191 (7)	0.0001 (7)	−0.0008 (7)	−0.0019 (6)
C11	0.0192 (7)	0.0204 (8)	0.0183 (7)	0.0023 (7)	−0.0005 (6)	−0.0011 (7)
C12	0.0211 (7)	0.0199 (8)	0.0160 (7)	−0.0014 (7)	0.0026 (6)	0.0000 (7)
C13	0.0214 (7)	0.0244 (8)	0.0186 (7)	0.0002 (8)	−0.0007 (6)	−0.0013 (7)
C14	0.0300 (9)	0.0221 (9)	0.0174 (7)	−0.0010 (8)	0.0022 (7)	0.0005 (7)
C15	0.0288 (9)	0.0225 (9)	0.0245 (8)	−0.0081 (8)	0.0027 (7)	−0.0014 (7)
C16	0.0238 (8)	0.0270 (9)	0.0230 (8)	−0.0053 (8)	−0.0035 (7)	−0.0026 (7)
C17	0.0250 (8)	0.0209 (8)	0.0193 (7)	−0.0004 (8)	−0.0026 (6)	0.0009 (7)

O1—C11	1.2208 (19)	C6—H6B	0.9900
N1—C14	1.375 (2)	C7—C9	1.530 (2)
N1—H1A	0.90 (3)	C7—C8	1.534 (2)
N1—H1B	0.91 (2)	C7—H7	1.0000
C1—C11	1.529 (2)	C8—H8A	0.9900
C1—C8	1.543 (2)	C8—H8B	0.9900
C1—C10	1.547 (2)	C9—H9A	0.9900
C1—C2	1.553 (2)	C9—H9B	0.9900
C2—C3	1.537 (2)	C10—H10A	0.9900
C2—H2A	0.9900	C10—H10B	0.9900
C2—H2B	0.9900	C11—C12	1.508 (2)
C3—C4	1.537 (2)	C12—C13	1.395 (2)
C3—C9	1.538 (2)	C12—C17	1.400 (2)
C3—H3	1.0000	C13—C14	1.398 (2)
C4—C5	1.535 (2)	C13—H13	0.9500
C4—H4A	0.9900	C14—C15	1.402 (2)
C4—H4B	0.9900	C15—C16	1.385 (2)
C5—C6	1.532 (2)	C15—H15	0.9500
C5—C10	1.535 (2)	C16—C17	1.386 (2)
C5—H5	1.0000	C16—H16	0.9500
C6—C7	1.538 (2)	C17—H17	0.9500
C6—H6A	0.9900
C14—N1—H1A	117.0 (16)	C9—C7—H7	109.4
C14—N1—H1B	117.0 (15)	C8—C7—H7	109.4
H1A—N1—H1B	120 (2)	C6—C7—H7	109.4
C11—C1—C8	108.68 (12)	C7—C8—C1	110.82 (13)
C11—C1—C10	111.41 (13)	C7—C8—H8A	109.5
C8—C1—C10	108.66 (12)	C1—C8—H8A	109.5
C11—C1—C2	111.02 (12)	C7—C8—H8B	109.5
C8—C1—C2	107.40 (12)	C1—C8—H8B	109.5
C10—C1—C2	109.56 (12)	H8A—C8—H8B	108.1
C3—C2—C1	109.96 (12)	C7—C9—C3	109.08 (13)
C3—C2—H2A	109.7	C7—C9—H9A	109.9
C1—C2—H2A	109.7	C3—C9—H9A	109.9
C3—C2—H2B	109.7	C7—C9—H9B	109.9
C1—C2—H2B	109.7	C3—C9—H9B	109.9
H2A—C2—H2B	108.2	H9A—C9—H9B	108.3
C2—C3—C4	109.58 (14)	C5—C10—C1	109.89 (13)
C2—C3—C9	109.77 (13)	C5—C10—H10A	109.7
C4—C3—C9	109.22 (13)	C1—C10—H10A	109.7
C2—C3—H3	109.4	C5—C10—H10B	109.7
C4—C3—H3	109.4	C1—C10—H10B	109.7
C9—C3—H3	109.4	H10A—C10—H10B	108.2
C5—C4—C3	109.79 (13)	O1—C11—C12	117.21 (14)
C5—C4—H4A	109.7	O1—C11—C1	119.54 (15)
C3—C4—H4A	109.7	C12—C11—C1	123.23 (13)
C5—C4—H4B	109.7	C13—C12—C17	119.21 (15)
C3—C4—H4B	109.7	C13—C12—C11	115.82 (14)
H4A—C4—H4B	108.2	C17—C12—C11	124.75 (15)
C6—C5—C4	109.22 (13)	C12—C13—C14	121.58 (15)
C6—C5—C10	109.66 (13)	C12—C13—H13	119.2
C4—C5—C10	109.91 (13)	C14—C13—H13	119.2
C6—C5—H5	109.3	N1—C14—C13	120.85 (16)
C4—C5—H5	109.3	N1—C14—C15	120.94 (17)
C10—C5—H5	109.3	C13—C14—C15	118.19 (15)
C5—C6—C7	109.25 (13)	C16—C15—C14	120.17 (16)
C5—C6—H6A	109.8	C16—C15—H15	119.9
C7—C6—H6A	109.8	C14—C15—H15	119.9
C5—C6—H6B	109.8	C15—C16—C17	121.31 (16)
C7—C6—H6B	109.8	C15—C16—H16	119.3
H6A—C6—H6B	108.3	C17—C16—H16	119.3
C9—C7—C8	109.21 (13)	C16—C17—C12	119.34 (15)
C9—C7—C6	109.85 (13)	C16—C17—H17	120.3
C8—C7—C6	109.60 (14)	C12—C17—H17	120.3

Cg1 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1i	0.91 (3)	2.10 (3)	3.003 (2)	168 (2)
N1—H1A···Cg1ii	0.90 (3)	2.54 (3)	3.316 (18)	144 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1i	0.91 (3)	2.10 (3)	3.003 (2)	168 (2)
N1—H1A⋯Cg1ii	0.90 (3)	2.54 (3)	3.316 (18)	144 (2)

Symmetry codes: (i) ; (ii) .