N-Phenyl­cyclo­hexa­necarboxamide

Abstract

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,

• a = 9.943 (2) Å

• b = 11.839 (2) Å

• c = 9.6514 (19) Å

• V = 1136.1 (4) ų

• 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[F ² > 2σ(F ²)] = 0.033

• wR(F ²) = 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

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.

Supplementary Material

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

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) .

supplementary crystallographic information

Comment

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).

Experimental

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

Refinement

Anomalous dispersion was negligible and Friedel pairs were merged before refinement. The amide H atom was located in a difference Fourier map and refined freely. The other H atoms were positioned geometrically and allowed to ride on their parent atoms [C—H = 1.00 (aliphic CH), 0.95(aromatic CH) or 0.99Å (CH₂), and U_iso(H) = 1.2 U_eq(C)]

Figures

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.

Crystal data

C13H17NO	F(000) = 440
Mr = 203.28	Dx = 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

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

Refinement

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(Fo2) + (0.0508P)2 + 0.0154P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
1431 reflections	Δρmax = 0.14 e Å−3
141 parameters	Δρmin = −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)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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 codes: (i) −x+1/2, y, z−1/2.