N-Phenyl­cyclo­hexa­necarboxamide

Dong, B.; Zhang, Y.; Wang, D.-Y.

doi:10.1107/S1600536810039267

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2763

https://doi.org/10.1107/S1600536810039267

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N-Phenylcyclohexanecarboxamide

Bin Dong,^a ^* Yu Zhang ^b and Dong-Yu Wang ^c

^aAffiliated Hospital of Hebei University, Baoding 071000, People's Republic of China, ^bHebei Xushui County Health Bureau, Baoding 071000, People's Republic of China, and ^cCollege of Electronic and Information Engineering, Hebei University, Baoding 071000, People's Republic of China
^*Correspondence e-mail: dbin2000@hotmail.com

(Received 29 September 2010; accepted 30 September 2010; online 9 October 2010)

In the title compound, C₁₃H₁₇NO, the cyclohexane ring adopts a chair conformation and the amide C(=O)—N moiety is almost coplanar with the phenyl ring [C—N—C—O = 4.1 (2)°]. In the crystal, molecules are linked to form a C(4) infinite [001] chain via N—H⋯O hydrogen bonds, unlike the cyclic motif seen in related structures.

Related literature

For hydrogen-bonding motifs in amides, see: Taylor et al. (1984 ); Leiserowitz & Schmidt (1969 ). For related structures, see: Lemmerer & Michael (2008 ).

Experimental

Crystal data

C₁₃H₁₇NO
M_r = 203.28
Orthorhombic, P c a 2₁
a = 9.943 (2) Å
b = 11.839 (2) Å
c = 9.6514 (19) Å
V = 1136.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.24 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.982, T_max = 0.993
8926 measured reflections
1431 independent reflections
1308 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.080
S = 1.09
1431 reflections
141 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.85 (3)	1.98 (3)	2.8145 (19)	171.7 (18)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810039267/hb5665sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039267/hb5665Isup2.hkl

checkCIF report

Comment top

The amides are an important H-bonding supramolecular synthon (Taylor et al., 1984; Leiserowitz & Schmidt, 1969), and we herein report the crystal structure of the title compound (I).

In the crystal structure of the title compound, Fig. 1, the cyclohexane group adopts a chair conformation [torsion angles: C1/C2/C3/C4 54.67 (19)°, C2/C3/C4/C5 - 55.3 (2)°]. The amide C(=O)—N moiety is almost coplanar with the phenyl ring [torsion angles: C8/N1/C7/O1 4.1 (2)°, C8/N1/C7/C6 - 175.38 (13)°]. Molecules are linked to form an infinite chain down the c axis via N—H···O hydrogen bonds (Fig. 2 and Table 1), being different from the reported secondary graph set R₆⁴(16) in 1-phenylcylcopentane- carboxamide and 1-(2-bromphenyl)cyclopentanecarboxamide (Lemmerer & Michael, 2008).

Related literature top

For hydrogen-bonding motifs in amides, see: Taylor et al. (1984); Leiserowitz & Schmidt (1969). For related structures, see: Lemmerer & Michael (2008).

Experimental top

The title compound was prepared from cyclohexoyl chloride and aniline. Colourless blocks of (I) were grown out via recrystallization from ethanol.

Structure description top

The amides are an important H-bonding supramolecular synthon (Taylor et al., 1984; Leiserowitz & Schmidt, 1969), and we herein report the crystal structure of the title compound (I).

For hydrogen-bonding motifs in amides, see: Taylor et al. (1984); Leiserowitz & Schmidt (1969). For related structures, see: Lemmerer & Michael (2008).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecule of (I) showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The infinite chain formed via N—H···O down the c axis.

N-Phenylcyclohexanecarboxamide top

Crystal data top

C₁₃H₁₇NO	F(000) = 440
M_r = 203.28	D_x = 1.188 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3664 reflections
a = 9.943 (2) Å	θ = 2.9–27.8°
b = 11.839 (2) Å	µ = 0.08 mm⁻¹
c = 9.6514 (19) Å	T = 113 K
V = 1136.1 (4) Å³	Block, colorless
Z = 4	0.24 × 0.18 × 0.10 mm

Data collection top

Rigaku Saturn CCD diffractometer	1431 independent reflections
Radiation source: rotating anode	1308 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.038
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 3.4°
ω and φ scans	h = −13→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −15→13
T_min = 0.982, T_max = 0.993	l = −12→12
8926 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0508P)² + 0.0154P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
1431 reflections	Δρ_max = 0.14 e Å⁻³
141 parameters	Δρ_min = −0.12 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.174 (16)

Crystal data top

C₁₃H₁₇NO	V = 1136.1 (4) Å³
M_r = 203.28	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 9.943 (2) Å	µ = 0.08 mm⁻¹
b = 11.839 (2) Å	T = 113 K
c = 9.6514 (19) Å	0.24 × 0.18 × 0.10 mm

Data collection top

Rigaku Saturn CCD diffractometer	1431 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1308 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.993	R_int = 0.038
8926 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.14 e Å⁻³
1431 reflections	Δρ_min = −0.12 e Å⁻³
141 parameters

Special details top

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 > 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	0.22562 (12)	0.24856 (10)	0.38081 (13)	0.0311 (3)
N1	0.17317 (13)	0.25866 (10)	0.15287 (15)	0.0201 (3)
C1	0.48835 (17)	0.24779 (12)	0.16381 (19)	0.0254 (4)
H1A	0.4512	0.2918	0.0854	0.031*
H1B	0.5133	0.3014	0.2382	0.031*
C2	0.61342 (18)	0.18387 (14)	0.11590 (18)	0.0282 (4)
H2A	0.5904	0.1367	0.0346	0.034*
H2B	0.6832	0.2387	0.0871	0.034*
C3	0.66924 (17)	0.10871 (15)	0.2307 (2)	0.0344 (4)
H3A	0.7032	0.1566	0.3071	0.041*
H3B	0.7457	0.0642	0.1941	0.041*
C4	0.56207 (18)	0.02845 (14)	0.2867 (2)	0.0334 (4)
H4A	0.5996	−0.0153	0.3651	0.040*
H4B	0.5356	−0.0255	0.2133	0.040*
C5	0.43777 (16)	0.09411 (13)	0.33568 (18)	0.0259 (4)
H5A	0.3681	0.0404	0.3679	0.031*
H5B	0.4625	0.1434	0.4146	0.031*
C6	0.38120 (15)	0.16622 (12)	0.21778 (17)	0.0218 (3)
H6	0.3575	0.1140	0.1401	0.026*
C7	0.25333 (16)	0.22777 (12)	0.25968 (16)	0.0207 (3)
C8	0.05357 (14)	0.32340 (12)	0.16232 (17)	0.0193 (3)
C9	−0.03152 (16)	0.31722 (13)	0.27635 (18)	0.0253 (4)
H9	−0.0110	0.2681	0.3513	0.030*
C10	−0.14675 (18)	0.38349 (15)	0.2797 (2)	0.0325 (4)
H10	−0.2045	0.3798	0.3580	0.039*
C11	−0.17880 (18)	0.45468 (14)	0.1711 (2)	0.0340 (4)
H11	−0.2574	0.5002	0.1750	0.041*
C12	−0.09518 (18)	0.45894 (13)	0.0565 (2)	0.0300 (4)
H12	−0.1174	0.5067	−0.0193	0.036*
C13	0.02102 (16)	0.39388 (13)	0.05141 (18)	0.0240 (3)
H13	0.0782	0.3974	−0.0274	0.029*
H1	0.204 (2)	0.2485 (15)	0.072 (3)	0.035 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0268 (6)	0.0522 (7)	0.0143 (6)	0.0088 (5)	−0.0021 (5)	−0.0028 (5)
N1	0.0190 (7)	0.0273 (6)	0.0138 (6)	0.0021 (5)	0.0007 (5)	−0.0007 (5)
C1	0.0241 (8)	0.0280 (8)	0.0241 (8)	0.0058 (6)	0.0028 (7)	0.0048 (7)
C2	0.0238 (9)	0.0310 (8)	0.0299 (9)	0.0038 (6)	0.0055 (7)	0.0028 (7)
C3	0.0240 (9)	0.0374 (9)	0.0418 (11)	0.0083 (7)	0.0003 (8)	0.0062 (8)
C4	0.0290 (9)	0.0291 (8)	0.0420 (10)	0.0068 (7)	−0.0009 (8)	0.0094 (8)
C5	0.0234 (8)	0.0268 (7)	0.0275 (8)	0.0017 (6)	−0.0010 (7)	0.0065 (7)
C6	0.0189 (7)	0.0242 (7)	0.0222 (7)	0.0028 (6)	−0.0003 (6)	0.0005 (6)
C7	0.0194 (7)	0.0238 (7)	0.0188 (7)	−0.0006 (6)	−0.0015 (6)	−0.0007 (6)
C8	0.0184 (7)	0.0198 (6)	0.0196 (7)	−0.0009 (5)	−0.0043 (6)	−0.0032 (6)
C9	0.0230 (8)	0.0303 (8)	0.0226 (8)	0.0025 (6)	−0.0014 (6)	−0.0008 (7)
C10	0.0226 (8)	0.0405 (9)	0.0345 (9)	0.0044 (7)	0.0008 (7)	−0.0063 (8)
C11	0.0249 (9)	0.0279 (8)	0.0493 (11)	0.0073 (6)	−0.0079 (8)	−0.0078 (8)
C12	0.0317 (10)	0.0219 (8)	0.0366 (9)	−0.0007 (6)	−0.0142 (8)	0.0017 (7)
C13	0.0232 (8)	0.0252 (7)	0.0236 (8)	−0.0040 (6)	−0.0063 (7)	0.0014 (7)

Geometric parameters (Å, º) top

O1—C7	1.226 (2)	C5—C6	1.530 (2)
N1—C7	1.353 (2)	C5—H5A	0.9900
N1—C8	1.4176 (19)	C5—H5B	0.9900
N1—H1	0.85 (3)	C6—C7	1.520 (2)
C1—C2	1.527 (2)	C6—H6	1.0000
C1—C6	1.529 (2)	C8—C9	1.390 (2)
C1—H1A	0.9900	C8—C13	1.395 (2)
C1—H1B	0.9900	C9—C10	1.389 (2)
C2—C3	1.526 (2)	C9—H9	0.9500
C2—H2A	0.9900	C10—C11	1.383 (3)
C2—H2B	0.9900	C10—H10	0.9500
C3—C4	1.527 (3)	C11—C12	1.385 (3)
C3—H3A	0.9900	C11—H11	0.9500
C3—H3B	0.9900	C12—C13	1.390 (2)
C4—C5	1.535 (2)	C12—H12	0.9500
C4—H4A	0.9900	C13—H13	0.9500
C4—H4B	0.9900

C7—N1—C8	126.23 (15)	C6—C5—H5B	109.6
C7—N1—H1	116.4 (15)	C4—C5—H5B	109.6
C8—N1—H1	116.4 (14)	H5A—C5—H5B	108.1
C2—C1—C6	110.94 (12)	C7—C6—C1	111.75 (12)
C2—C1—H1A	109.5	C7—C6—C5	112.16 (13)
C6—C1—H1A	109.5	C1—C6—C5	110.46 (13)
C2—C1—H1B	109.5	C7—C6—H6	107.4
C6—C1—H1B	109.5	C1—C6—H6	107.4
H1A—C1—H1B	108.0	C5—C6—H6	107.4
C3—C2—C1	111.43 (14)	O1—C7—N1	122.67 (15)
C3—C2—H2A	109.3	O1—C7—C6	122.53 (14)
C1—C2—H2A	109.3	N1—C7—C6	114.80 (14)
C3—C2—H2B	109.3	C9—C8—C13	119.85 (14)
C1—C2—H2B	109.3	C9—C8—N1	122.21 (14)
H2A—C2—H2B	108.0	C13—C8—N1	117.94 (14)
C2—C3—C4	111.49 (14)	C10—C9—C8	119.40 (15)
C2—C3—H3A	109.3	C10—C9—H9	120.3
C4—C3—H3A	109.3	C8—C9—H9	120.3
C2—C3—H3B	109.3	C11—C10—C9	121.10 (18)
C4—C3—H3B	109.3	C11—C10—H10	119.4
H3A—C3—H3B	108.0	C9—C10—H10	119.4
C3—C4—C5	110.85 (13)	C10—C11—C12	119.33 (16)
C3—C4—H4A	109.5	C10—C11—H11	120.3
C5—C4—H4A	109.5	C12—C11—H11	120.3
C3—C4—H4B	109.5	C11—C12—C13	120.47 (17)
C5—C4—H4B	109.5	C11—C12—H12	119.8
H4A—C4—H4B	108.1	C13—C12—H12	119.8
C6—C5—C4	110.48 (14)	C12—C13—C8	119.83 (16)
C6—C5—H5A	109.6	C12—C13—H13	120.1
C4—C5—H5A	109.6	C8—C13—H13	120.1

C6—C1—C2—C3	−55.5 (2)	C1—C6—C7—N1	78.01 (17)
C1—C2—C3—C4	54.7 (2)	C5—C6—C7—N1	−157.32 (13)
C2—C3—C4—C5	−55.3 (2)	C7—N1—C8—C9	−32.8 (2)
C3—C4—C5—C6	56.9 (2)	C7—N1—C8—C13	148.20 (15)
C2—C1—C6—C7	−177.32 (14)	C13—C8—C9—C10	−1.4 (2)
C2—C1—C6—C5	57.07 (19)	N1—C8—C9—C10	179.54 (15)
C4—C5—C6—C7	176.87 (13)	C8—C9—C10—C11	0.6 (2)
C4—C5—C6—C1	−57.75 (17)	C9—C10—C11—C12	0.7 (3)
C8—N1—C7—O1	4.1 (2)	C10—C11—C12—C13	−1.1 (2)
C8—N1—C7—C6	−175.38 (13)	C11—C12—C13—C8	0.2 (2)
C1—C6—C7—O1	−101.43 (19)	C9—C8—C13—C12	1.0 (2)
C5—C6—C7—O1	23.2 (2)	N1—C8—C13—C12	−179.90 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.85 (3)	1.98 (3)	2.8145 (19)	171.7 (18)

Symmetry code: (i) −x+1/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₇NO
M_r	203.28
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	113
a, b, c (Å)	9.943 (2), 11.839 (2), 9.6514 (19)
V (Å³)	1136.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.18 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.982, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	8926, 1431, 1308
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.080, 1.09
No. of reflections	1431
No. of parameters	141
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.12

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.85 (3)	1.98 (3)	2.8145 (19)	171.7 (18)

Symmetry code: (i) −x+1/2, y, z−1/2.

Acknowledgements

This paper was supported by the Hebei Province Health Bureau (grant No. 20090176), the Ministry of Science and Technology of the People's Republic of China International Cooperation Project (grant No. 2008DFR10530) and the Science and Technology Support Program of Hebei Province Science and Technology Department (grant No. 08243531D).

References

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