N-Cyclo­hexyl-2-oxo-2-phenyl­acetamide

Jia, Z.-J.; Wu, J.-L.

doi:10.1107/S1600536812023549

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1948

doi:10.1107/S1600536812023549

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N-Cyclohexyl-2-oxo-2-phenylacetamide

Ze-Jun Jia ^a and Jin-Long Wu ^a ^*

^aLaboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, People's Republic of China
^*Correspondence e-mail: wyz@zju.edu.cn

(Received 11 May 2012; accepted 23 May 2012; online 31 May 2012)

In the title compound, C₁₄H₁₇NO₂, the two carbonyl groups are oriented with respect to each other with a torsion angle of −129.9 (3)°. The cyclohexane ring adopts a chair conformation. In the crystal, molecules 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 ); Dai & Wu (2011 ).

Experimental

Crystal data

C₁₄H₁₇NO₂
M_r = 231.29
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.082
S = 1.00
1737 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.08 e Å⁻³
Δρ_min = −0.10 e Å⁻³

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

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812023549/xu5541sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812023549/xu5541Isup3.cml

checkCIF report

Comment top

Several crystals of N-substituted phenylglyoxamide have been reported, and their great differences of the cystal form due to the N—H···O hydrogen bond linking form have been observed (Boryczka et al., 1998; Dai & Wu, 2011). In our research for exploring the effect rule of the N-substituted group of phenylglyoxamide to the crystal form, we have synthesized the title compound by condensation of phenylglyoxic acid with cyclohexylamine. The structure of the title compound has been characterized by spectroscopic methods and further confirmation by X-ray analysis. We report here its crystal structure. The two carbonyl groups of the molecule are oriented to each other with a torsion angle of -129.9 (3)°. Molecules are linked by intermolecular hydrogen bonds N—H···O into a one-dimensional chain (Fig. 2).

Related literature top

For related N-substituted 2-oxo-2-phenylacetamides, see: Boryczka et al. (1998); Dai & Wu (2011).

Experimental top

Into a suspension of phenylglyoxylic acid (400 mg, 2.67 mmol) and cyclohexylamine (0.272 ml, 2.38 mmol) in methylene chloride (10 ml), N,N'-dicyclohexylcarbodiimide (DCC) (540 mg, 2.62 mmol) and 4-(dimethylamino)pyridine (DMAP) (66 mg, 0.54 mmol) was added respectively at room temperature and continuted stirring for 10 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure, the residue was purified by colum chromatography (silica gel, 30% of ethyl acetate in hexane) to afford the title compound in 69% yield (379 mg) as a white solid, m.p. 384–385 K. Single crystals suitable for X-ray diffraction of the title compound were grown in a mixture of ethyl acetate and hexane.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 40% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. One-dimensional chain molecules of the title compound linked by two adjacent moleculars N—H···O hydrogen bonds (dotted lines). Symmetry code: (i) -0.5 + x, 0.5 - y, 1 - z.

N-Cyclohexyl-2-oxo-2-phenylacetamide top

Crystal data top

C₁₄H₁₇NO₂	F(000) = 496
M_r = 231.29	D_x = 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

Data collection top

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

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.032P)²] where P = (F_o² + 2F_c²)/3
1737 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.08 e Å⁻³
0 restraints	Δρ_min = −0.10 e Å⁻³

Crystal data top

C₁₄H₁₇NO₂	V = 1336.87 (12) Å³
M_r = 231.29	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.6942 (4) Å	µ = 0.08 mm⁻¹
b = 10.4394 (6) Å	T = 153 K
c = 13.2100 (8) Å	0.25 × 0.16 × 0.12 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	845 reflections with I > 2σ(I)
5120 measured reflections	R_int = 0.026
1737 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.00	Δρ_max = 0.08 e Å⁻³
1737 reflections	Δρ_min = −0.10 e Å⁻³
154 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇NO₂
M_r	231.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	153
a, b, c (Å)	9.6942 (4), 10.4394 (6), 13.2100 (8)
V (Å³)	1336.87 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5120, 1737, 845
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.082, 1.00
No. of reflections	1737
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.08, −0.10

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, −z+1.

Acknowledgements

The authors thank Mr J. Gu for valuable suggestions and Mr J. Liu for assistance with the data collection.

References

Boryczka, S., Suwinska, K., Le Guillanton, G., Do, Q. T. & Elothmani, D. (1998). J. Chem. Crystallogr. 28, 555–560. Web of Science CSD CrossRef CAS Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dai, J. & Wu, J.-L. (2011). Acta Cryst. E67, o3152. Web of Science CSD CrossRef IUCr Journals Google Scholar
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