Phenyl N-cyclo­hexyl­carbamate

Shahwar, D.; Tahir, M.N.; Ahmad, N.; Ullah, S.; Khan, M.A.

doi:10.1107/S1600536809050806

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o22

doi:10.1107/S1600536809050806

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Phenyl N-cyclohexylcarbamate

Durre Shahwar,^a M. Nawaz Tahir,^b ^* Naeem Ahmad,^a Sami Ullah ^a and Muhammad Akmal Khan ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 22 November 2009; accepted 25 November 2009; online 4 December 2009)

In the title compound, C₁₃H₁₇NO₂, the dihedral angle between the benzene ring and the basal plane of the cyclohexyl ring is 49.55 (8)°. In the crystal, molecules 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_r = 219.28
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.127
S = 0.99
2265 reflections
145 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

The crystal structures of (II) phenyl piperidine-1-carboxylate (Shahwar et al., 2010), (III) phenyl N-(2-methylphenyl)carbamate (Shahwar et al., 2009a) and (IV) phenyl N-phenylcarbamate (Shahwar et al., 2009b) have been reported by us. In continuation to synthesize various carbamates for the study of biological activities, the title compound (I, Fig. 1) is being reported.

In (I), the benzene ring A (C1—C6) is of course planar. The central carbamate group B (O1/O2/C7/N1) and the basal plane C (C9/C10/C12/C13) of cyclohexyl are also planar with maximum r. m. s. deviations of 0.002 and 0.005 Å respectively, from the respective mean square planes. The dihedral angles between A/B, B/C and A/C are 76.26 (8)°, 70.99 (9)° and 52.17 (7)° respectively. The cyclohexyl ring is in the chair conformation with the apical atoms C8 and C11 are at a distance of 0.652 (3) and -0.668 (4) Å respectively, from the basal plane (C9/C10/C12/C13). The molecules are stabilized in the form of polymeric chains (Table 1, Fig. 2).

Related literature top

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

Experimental top

Cyclohexylamine (0.01 M, 1.15 ml) and triethylamine (0.012 M, 1.66 ml) were added to 20 ml dichloromethane in a 50 ml round bottom flask equipped with magnetic stirrer. Phenyl chloroformate (0.01 M, 1.26 ml) was added drop wise with continuous stirring of the contents of the flask. After complete addition the stirring was continued for 30 minutes. Extra dichloromethane was evaporated and then resulting solid was washed with 1M HCl and filtered to get pure product. Recrystallization of the crude product with ethyl acetate affoarded colourless needles of (I).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The partial packing of (I), which shows that molecules form infinite chains.

Phenyl N-cyclohexylcarbamate top

Crystal data top

C₁₃H₁₇NO₂	F(000) = 472
M_r = 219.28	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	2265 independent reflections
Radiation source: fine-focus sealed tube	1207 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 7.90 pixels mm^-1	θ_max = 25.4°, θ_min = 2.8°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
T_min = 0.987, T_max = 0.993	l = −13→13
10855 measured reflections

Refinement top

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(F_o²) + (0.0463P)² + 0.1974P] where P = (F_o² + 2F_c²)/3
2265 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₃H₁₇NO₂	V = 1235.49 (19) Å³
M_r = 219.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4724 (11) Å	µ = 0.08 mm⁻¹
b = 9.3554 (8) Å	T = 296 K
c = 11.5212 (10) Å	0.28 × 0.11 × 0.09 mm
β = 92.380 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2265 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1207 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.993	R_int = 0.043
10855 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.12 e Å⁻³
2265 reflections	Δρ_min = −0.16 e Å⁻³
145 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₇NO₂
M_r	219.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.4724 (11), 9.3554 (8), 11.5212 (10)
β (°)	92.380 (5)
V (Å³)	1235.49 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.11 × 0.09

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.987, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	10855, 2265, 1207
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.127, 0.99
No. of reflections	2265
No. of parameters	145
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+1/2.

Acknowledgements

DS is grateful to Dr I. U. Khan and M. N. Arshad for their assistance with the data collection.

References

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