N-Cyclo-hexyl-2-oxo-2-phenyl-acetamide.

In the title compound, C(14)H(17)NO(2), the two carbonyl groups are oriented with respect to each other with a torsion angle of -129.9 (3)°. The cyclo-hexane ring adopts a chair conformation. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into a chain running along the a axis.

Related literature

For related N-substituted 2-oxo-2-phenyl­acetamides, see: Boryczka et al. (1998 ▶); n class="Gene">Dai & Wu (2011 ▶).

Experimental

Crystal data

C14H17NO2

M = 231.29

Orthorhombic,

a = 9.6942 (4) Å

b = 10.4394 (6) Å

c = 13.2100 (8) Å

V = 1336.87 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 153 K

0.25 × 0.16 × 0.12 mm

Data collection

Bruker SMART 1000 CCD diffractometer

5120 measured reflections

1737 independent reflections

845 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.082

S = 1.00

1737 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.08 e Å−3

Δρmin = −0.10 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL ; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023549/xu5541sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023549/xu5541Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023549/xu5541Isup3.cml

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

C14H17NO2	F(000) = 496
Mr = 231.29	Dx = 1.149 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6354 reflections
a = 9.6942 (4) Å	θ = 3.2–27.5°
b = 10.4394 (6) Å	µ = 0.08 mm−1
c = 13.2100 (8) Å	T = 153 K
V = 1336.87 (12) Å3	Block, colourless
Z = 4	0.25 × 0.16 × 0.12 mm

Bruker SMART 1000 CCD diffractometer	845 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 27.5°, θmin = 3.3°
φ and ω scans	h = −10→12
5120 measured reflections	k = −9→13
1737 independent reflections	l = −10→16

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.032P)2] where P = (Fo2 + 2Fc2)/3
1737 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.08 e Å−3
0 restraints	Δρmin = −0.10 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.4098 (2)	0.2794 (2)	0.45295 (19)	0.0663 (6)
C2	0.3397 (2)	0.3534 (2)	0.3683 (2)	0.0684 (7)
C3	0.3856 (2)	0.3354 (2)	0.2645 (2)	0.0667 (6)
C4	0.4675 (3)	0.2327 (3)	0.2370 (3)	0.0863 (7)
H4	0.4986	0.1749	0.2876	0.104*
C5	0.5046 (4)	0.2127 (4)	0.1389 (4)	0.1220 (11)
H5	0.5598	0.1408	0.1216	0.146*
C6	0.4629 (6)	0.2948 (6)	0.0663 (3)	0.1472 (17)
H6	0.4902	0.2810	−0.0019	0.177*
C7	0.3812 (4)	0.3986 (5)	0.0898 (4)	0.1328 (15)
H7	0.3525	0.4561	0.0382	0.159*
C8	0.3411 (3)	0.4187 (3)	0.1896 (3)	0.0992 (9)
H8	0.2834	0.4891	0.2064	0.119*
C9	0.37782 (19)	0.1451 (2)	0.60266 (19)	0.0663 (6)
H9	0.4801	0.1356	0.5966	0.080*
C10	0.3146 (2)	0.0142 (2)	0.6000 (2)	0.0774 (7)
H10A	0.3387	−0.0284	0.5355	0.093*
H10B	0.2130	0.0217	0.6035	0.093*
C11	0.3656 (3)	−0.0661 (3)	0.6877 (2)	0.0963 (9)
H11A	0.3203	−0.1511	0.6857	0.116*
H11B	0.4663	−0.0794	0.6811	0.116*
C12	0.3357 (3)	−0.0036 (3)	0.7859 (2)	0.1077 (10)
H12A	0.3754	−0.0557	0.8413	0.129*
H12B	0.2346	0.0002	0.7960	0.129*
C13	0.3938 (3)	0.1297 (3)	0.7912 (2)	0.1173 (11)
H13A	0.4958	0.1252	0.7919	0.141*
H13B	0.3635	0.1709	0.8549	0.141*
C14	0.3468 (3)	0.2104 (3)	0.7015 (2)	0.0926 (8)
H14A	0.2463	0.2259	0.7067	0.111*
H14B	0.3941	0.2944	0.7035	0.111*
N1	0.32939 (16)	0.22256 (17)	0.51791 (15)	0.0709 (6)
H1	0.2397	0.2315	0.5102	0.085*
O1	0.53605 (14)	0.27896 (19)	0.45723 (13)	0.1065 (7)
O2	0.24786 (18)	0.42743 (18)	0.39078 (16)	0.1070 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0406 (12)	0.0839 (14)	0.0744 (18)	−0.0046 (11)	0.0022 (12)	0.0129 (15)
C2	0.0468 (12)	0.0696 (14)	0.089 (2)	0.0002 (12)	0.0027 (14)	0.0158 (15)
C3	0.0585 (13)	0.0672 (14)	0.074 (2)	−0.0106 (13)	−0.0036 (14)	0.0135 (15)
C4	0.0808 (16)	0.0898 (18)	0.088 (2)	−0.0109 (17)	0.0028 (17)	0.0012 (17)
C5	0.137 (3)	0.125 (3)	0.104 (3)	−0.020 (2)	0.027 (3)	−0.016 (3)
C6	0.188 (4)	0.167 (4)	0.087 (3)	−0.077 (4)	0.014 (3)	−0.015 (3)
C7	0.158 (3)	0.148 (3)	0.093 (3)	−0.044 (3)	−0.029 (3)	0.054 (3)
C8	0.107 (2)	0.0941 (18)	0.097 (3)	−0.0214 (17)	−0.015 (2)	0.030 (2)
C9	0.0369 (10)	0.0915 (15)	0.0706 (18)	−0.0062 (11)	0.0024 (12)	0.0167 (16)
C10	0.0801 (15)	0.0763 (16)	0.0757 (19)	0.0060 (14)	−0.0005 (16)	0.0040 (15)
C11	0.0945 (19)	0.0939 (17)	0.101 (3)	0.0056 (16)	0.0059 (19)	0.0259 (19)
C12	0.102 (2)	0.144 (3)	0.077 (3)	0.005 (2)	0.005 (2)	0.037 (2)
C13	0.131 (2)	0.145 (3)	0.076 (2)	−0.012 (2)	−0.026 (2)	−0.007 (2)
C14	0.0999 (19)	0.0907 (17)	0.087 (2)	−0.0083 (17)	−0.0252 (18)	−0.0073 (18)
N1	0.0344 (8)	0.0975 (13)	0.0809 (15)	−0.0005 (9)	0.0012 (9)	0.0273 (12)
O1	0.0367 (8)	0.1821 (17)	0.1007 (15)	−0.0129 (10)	−0.0007 (9)	0.0534 (14)
O2	0.0890 (12)	0.1142 (14)	0.1178 (17)	0.0351 (12)	0.0181 (13)	0.0217 (14)

C1—O1	1.226 (2)	C9—C14	1.504 (3)
C1—N1	1.302 (2)	C9—H9	1.0000
C1—C2	1.519 (3)	C10—C11	1.512 (3)
C2—O2	1.216 (3)	C10—H10A	0.9900
C2—C3	1.454 (3)	C10—H10B	0.9900
C3—C4	1.383 (3)	C11—C12	1.481 (4)
C3—C8	1.386 (3)	C11—H11A	0.9900
C4—C5	1.360 (4)	C11—H11B	0.9900
C4—H4	0.9500	C12—C13	1.502 (4)
C5—C6	1.348 (5)	C12—H12A	0.9900
C5—H5	0.9500	C12—H12B	0.9900
C6—C7	1.378 (5)	C13—C14	1.524 (3)
C6—H6	0.9500	C13—H13A	0.9900
C7—C8	1.390 (5)	C13—H13B	0.9900
C7—H7	0.9500	C14—H14A	0.9900
C8—H8	0.9500	C14—H14B	0.9900
C9—N1	1.459 (3)	N1—H1	0.8800
C9—C10	1.498 (3)
O1—C1—N1	124.4 (2)	C11—C10—H10A	109.5
O1—C1—C2	118.8 (2)	C9—C10—H10B	109.5
N1—C1—C2	116.70 (18)	C11—C10—H10B	109.5
O2—C2—C3	122.5 (2)	H10A—C10—H10B	108.1
O2—C2—C1	118.1 (3)	C12—C11—C10	111.3 (2)
C3—C2—C1	119.5 (2)	C12—C11—H11A	109.4
C4—C3—C8	118.5 (3)	C10—C11—H11A	109.4
C4—C3—C2	121.6 (2)	C12—C11—H11B	109.4
C8—C3—C2	119.8 (3)	C10—C11—H11B	109.4
C5—C4—C3	121.4 (3)	H11A—C11—H11B	108.0
C5—C4—H4	119.3	C11—C12—C13	112.1 (3)
C3—C4—H4	119.3	C11—C12—H12A	109.2
C6—C5—C4	120.1 (4)	C13—C12—H12A	109.2
C6—C5—H5	120.0	C11—C12—H12B	109.2
C4—C5—H5	120.0	C13—C12—H12B	109.2
C5—C6—C7	120.8 (4)	H12A—C12—H12B	107.9
C5—C6—H6	119.6	C12—C13—C14	111.3 (3)
C7—C6—H6	119.6	C12—C13—H13A	109.4
C6—C7—C8	119.5 (4)	C14—C13—H13A	109.4
C6—C7—H7	120.2	C12—C13—H13B	109.4
C8—C7—H7	120.2	C14—C13—H13B	109.4
C3—C8—C7	119.7 (3)	H13A—C13—H13B	108.0
C3—C8—H8	120.2	C9—C14—C13	111.4 (2)
C7—C8—H8	120.2	C9—C14—H14A	109.4
N1—C9—C10	110.88 (19)	C13—C14—H14A	109.4
N1—C9—C14	110.53 (19)	C9—C14—H14B	109.4
C10—C9—C14	110.6 (2)	C13—C14—H14B	109.4
N1—C9—H9	108.2	H14A—C14—H14B	108.0
C10—C9—H9	108.2	C1—N1—C9	124.46 (16)
C14—C9—H9	108.2	C1—N1—H1	117.8
C9—C10—C11	110.8 (2)	C9—N1—H1	117.8
C9—C10—H10A	109.5
O1—C1—C2—O2	−129.9 (3)	C2—C3—C8—C7	−177.8 (3)
N1—C1—C2—O2	48.6 (3)	C6—C7—C8—C3	1.1 (5)
O1—C1—C2—C3	49.1 (3)	N1—C9—C10—C11	179.74 (19)
N1—C1—C2—C3	−132.4 (2)	C14—C9—C10—C11	−57.3 (3)
O2—C2—C3—C4	−165.7 (2)	C9—C10—C11—C12	57.3 (3)
C1—C2—C3—C4	15.4 (3)	C10—C11—C12—C13	−55.3 (3)
O2—C2—C3—C8	10.9 (3)	C11—C12—C13—C14	53.3 (4)
C1—C2—C3—C8	−168.0 (2)	N1—C9—C14—C13	178.8 (2)
C8—C3—C4—C5	0.0 (4)	C10—C9—C14—C13	55.6 (3)
C2—C3—C4—C5	176.7 (2)	C12—C13—C14—C9	−53.3 (3)
C3—C4—C5—C6	0.9 (5)	O1—C1—N1—C9	−3.0 (4)
C4—C5—C6—C7	−0.9 (6)	C2—C1—N1—C9	178.6 (2)
C5—C6—C7—C8	−0.1 (6)	C10—C9—N1—C1	−125.1 (2)
C4—C3—C8—C7	−1.1 (4)	C14—C9—N1—C1	111.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.02	2.863 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.02	2.863 (2)	159

Symmetry code: (i) .