Phenyl N-cyclo-hexyl-carbamate.

In the title compound, C(13)H(17)NO(2), the dihedral angle between the benzene ring and the basal plane of the cyclo-hexyl ring is 49.55 (8)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains propagating in [010].

Related literature

For related structures, see: Shahwar et al. (2009a ▶,b ▶, 2010 ▶).

Experimental

Crystal data

C13H17NO2

M = 219.28

Monoclinic,

a = 11.4724 (11) Å

b = 9.3554 (8) Å

c = 11.5212 (10) Å

β = 92.380 (5)°

V = 1235.49 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.28 × 0.11 × 0.09 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.987, T max = 0.993

10855 measured reflections

2265 independent reflections

1207 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 0.99

2265 reflections

145 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050806/hb5247sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050806/hb5247Isup2.hkl

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

C13H17NO2	F(000) = 472
Mr = 219.28	Dx = 1.179 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2265 reflections
a = 11.4724 (11) Å	θ = 2.8–25.4°
b = 9.3554 (8) Å	µ = 0.08 mm−1
c = 11.5212 (10) Å	T = 296 K
β = 92.380 (5)°	Needle, colourless
V = 1235.49 (19) Å3	0.28 × 0.11 × 0.09 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2265 independent reflections
Radiation source: fine-focus sealed tube	1207 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 7.90 pixels mm-1	θmax = 25.4°, θmin = 2.8°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.987, Tmax = 0.993	l = −13→13
10855 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.1974P] where P = (Fo2 + 2Fc2)/3
2265 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > σ(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	−0.09944 (15)	0.52058 (14)	0.31355 (14)	0.0774 (7)
O2	−0.03969 (14)	0.74215 (15)	0.26826 (13)	0.0704 (6)
N1	0.06141 (17)	0.54662 (18)	0.21748 (16)	0.0592 (7)
C1	−0.1882 (2)	0.5766 (2)	0.3782 (2)	0.0562 (9)
C2	−0.16451 (18)	0.62858 (16)	0.48728 (15)	0.0657 (10)
C3	−0.25438 (18)	0.67436 (16)	0.55214 (15)	0.0756 (10)
C4	−0.3657 (3)	0.6653 (3)	0.5093 (3)	0.0874 (12)
C5	−0.3892 (3)	0.6127 (3)	0.4005 (3)	0.0941 (12)
C6	−0.2992 (3)	0.5681 (3)	0.3342 (2)	0.0769 (11)
C7	−0.0243 (2)	0.6158 (2)	0.26526 (17)	0.0513 (8)
C8	0.15329 (19)	0.6175 (2)	0.15547 (17)	0.0503 (8)
C9	0.1297 (2)	0.6138 (2)	0.02537 (18)	0.0640 (9)
C10	0.2269 (2)	0.6843 (3)	−0.03874 (19)	0.0759 (10)
C11	0.3421 (2)	0.6149 (3)	−0.0078 (2)	0.0790 (11)
C12	0.3672 (2)	0.6198 (3)	0.1221 (2)	0.0861 (11)
C13	0.2694 (2)	0.5510 (3)	0.18732 (19)	0.0687 (10)
H1N	0.0588 (19)	0.456 (2)	0.2198 (17)	0.0710*
H2	−0.08804	0.63285	0.51718	0.0788*
H3	−0.23893	0.71187	0.62593	0.0905*
H4	−0.42659	0.69512	0.55435	0.1045*
H5	−0.46588	0.60696	0.37127	0.1126*
H6	−0.31450	0.53240	0.25975	0.0923*
H8	0.15598	0.71776	0.17996	0.0604*
H9A	0.05675	0.66261	0.00635	0.0768*
H9B	0.12155	0.51529	0.00004	0.0768*
H10A	0.21067	0.67673	−0.12180	0.0910*
H10B	0.23069	0.78500	−0.01876	0.0910*
H11A	0.40367	0.66398	−0.04704	0.0947*
H11B	0.34065	0.51622	−0.03374	0.0947*
H12A	0.37630	0.71850	0.14666	0.1033*
H12B	0.43979	0.57023	0.14083	0.1033*
H13A	0.26646	0.44966	0.16960	0.0825*
H13B	0.28555	0.56132	0.27021	0.0825*

	U11	U22	U33	U12	U13	U23
O1	0.0806 (13)	0.0403 (9)	0.1156 (13)	−0.0035 (8)	0.0577 (11)	−0.0012 (8)
O2	0.0816 (13)	0.0329 (8)	0.0991 (12)	0.0038 (8)	0.0325 (9)	0.0029 (8)
N1	0.0672 (14)	0.0331 (9)	0.0796 (14)	−0.0014 (10)	0.0321 (11)	0.0008 (9)
C1	0.0607 (18)	0.0409 (12)	0.0687 (16)	0.0029 (11)	0.0232 (14)	0.0050 (11)
C2	0.0613 (18)	0.0572 (14)	0.0786 (18)	−0.0003 (12)	0.0025 (14)	0.0031 (13)
C3	0.094 (2)	0.0744 (17)	0.0594 (16)	0.0046 (16)	0.0156 (16)	0.0005 (12)
C4	0.077 (2)	0.102 (2)	0.086 (2)	0.0202 (17)	0.0361 (18)	0.0012 (16)
C5	0.056 (2)	0.127 (2)	0.099 (2)	0.0117 (16)	0.0010 (17)	−0.0054 (19)
C6	0.078 (2)	0.0915 (19)	0.0615 (17)	0.0040 (15)	0.0065 (16)	−0.0072 (13)
C7	0.0600 (16)	0.0359 (12)	0.0593 (13)	−0.0039 (11)	0.0165 (11)	0.0001 (10)
C8	0.0569 (16)	0.0398 (11)	0.0553 (14)	−0.0073 (10)	0.0152 (11)	−0.0018 (9)
C9	0.0624 (18)	0.0666 (15)	0.0628 (15)	−0.0008 (12)	0.0012 (13)	0.0054 (11)
C10	0.093 (2)	0.0819 (17)	0.0537 (15)	−0.0121 (16)	0.0139 (15)	0.0079 (12)
C11	0.072 (2)	0.097 (2)	0.0701 (18)	−0.0193 (15)	0.0284 (15)	−0.0077 (14)
C12	0.0556 (19)	0.124 (2)	0.0791 (19)	−0.0113 (16)	0.0093 (14)	0.0037 (16)
C13	0.0644 (19)	0.0845 (17)	0.0572 (15)	0.0016 (13)	0.0025 (13)	0.0076 (12)

O1—C1	1.389 (3)	C12—C13	1.519 (3)
O1—C7	1.373 (3)	C2—H2	0.9300
O2—C7	1.196 (2)	C3—H3	0.9300
N1—C7	1.317 (3)	C4—H4	0.9300
N1—C8	1.457 (3)	C5—H5	0.9300
N1—H1N	0.849 (19)	C6—H6	0.9300
C1—C2	1.364 (3)	C8—H8	0.9800
C1—C6	1.353 (4)	C9—H9A	0.9700
C2—C3	1.367 (3)	C9—H9B	0.9700
C3—C4	1.353 (4)	C10—H10A	0.9700
C4—C5	1.363 (5)	C10—H10B	0.9700
C5—C6	1.375 (5)	C11—H11A	0.9700
C8—C13	1.502 (3)	C11—H11B	0.9700
C8—C9	1.512 (3)	C12—H12A	0.9700
C9—C10	1.514 (3)	C12—H12B	0.9700
C10—C11	1.502 (3)	C13—H13A	0.9700
C11—C12	1.513 (3)	C13—H13B	0.9700
C1—O1—C7	117.32 (15)	C1—C6—H6	120.00
C7—N1—C8	123.31 (17)	C5—C6—H6	120.00
C7—N1—H1N	116.7 (15)	N1—C8—H8	108.00
C8—N1—H1N	119.8 (14)	C9—C8—H8	108.00
O1—C1—C2	120.4 (2)	C13—C8—H8	108.00
O1—C1—C6	118.5 (2)	C8—C9—H9A	109.00
C2—C1—C6	121.0 (2)	C8—C9—H9B	109.00
C1—C2—C3	119.29 (19)	C10—C9—H9A	109.00
C2—C3—C4	120.2 (2)	C10—C9—H9B	109.00
C3—C4—C5	120.4 (3)	H9A—C9—H9B	108.00
C4—C5—C6	119.8 (3)	C9—C10—H10A	110.00
C1—C6—C5	119.4 (2)	C9—C10—H10B	110.00
O1—C7—O2	122.3 (2)	C11—C10—H10A	109.00
O1—C7—N1	110.04 (16)	C11—C10—H10B	109.00
O2—C7—N1	127.7 (2)	H10A—C10—H10B	108.00
N1—C8—C9	111.85 (17)	C10—C11—H11A	110.00
C9—C8—C13	110.68 (17)	C10—C11—H11B	110.00
N1—C8—C13	110.12 (17)	C12—C11—H11A	110.00
C8—C9—C10	111.62 (18)	C12—C11—H11B	109.00
C9—C10—C11	110.8 (2)	H11A—C11—H11B	108.00
C10—C11—C12	110.56 (19)	C11—C12—H12A	109.00
C11—C12—C13	111.24 (19)	C11—C12—H12B	109.00
C8—C13—C12	111.7 (2)	C13—C12—H12A	109.00
C1—C2—H2	120.00	C13—C12—H12B	109.00
C3—C2—H2	120.00	H12A—C12—H12B	108.00
C2—C3—H3	120.00	C8—C13—H13A	109.00
C4—C3—H3	120.00	C8—C13—H13B	109.00
C3—C4—H4	120.00	C12—C13—H13A	109.00
C5—C4—H4	120.00	C12—C13—H13B	109.00
C4—C5—H5	120.00	H13A—C13—H13B	108.00
C6—C5—H5	120.00
C7—O1—C1—C2	−75.3 (2)	C1—C2—C3—C4	1.4 (3)
C7—O1—C1—C6	109.8 (2)	C2—C3—C4—C5	−1.1 (4)
C1—O1—C7—O2	−7.1 (3)	C3—C4—C5—C6	0.3 (4)
C1—O1—C7—N1	173.43 (18)	C4—C5—C6—C1	0.2 (4)
C8—N1—C7—O1	177.79 (18)	N1—C8—C9—C10	−178.57 (18)
C8—N1—C7—O2	−1.7 (4)	C13—C8—C9—C10	−55.4 (2)
C7—N1—C8—C9	−98.5 (2)	N1—C8—C13—C12	178.63 (18)
C7—N1—C8—C13	138.0 (2)	C9—C8—C13—C12	54.5 (2)
O1—C1—C2—C3	−175.67 (16)	C8—C9—C10—C11	56.9 (2)
C6—C1—C2—C3	−0.9 (3)	C9—C10—C11—C12	−56.8 (3)
O1—C1—C6—C5	175.0 (2)	C10—C11—C12—C13	56.1 (3)
C2—C1—C6—C5	0.1 (4)	C11—C12—C13—C8	−55.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.849 (19)	2.018 (19)	2.865 (2)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.849 (19)	2.018 (19)	2.865 (2)	175 (2)

Symmetry code: (i) .