4-Chloro-N-cyclo-hexyl-benzamide.

In the title compound, C(13)H(16)ClNO, the cyclo-hexyl ring adopts a chair conformation, with puckering parameters Q = 0.576 (3) Å, θ = 0.1 (3) and ϕ = 8 (15)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link mol-ecules into one-dimensional chains propagating in [010].

Related literature

For applications of N-substituted benzamides, see: Beccalli et al. (2005 ▶); Calderone et al. (2006 ▶); Vega-Noverola et al. (1989 ▶); Zhichkin et al. (2007 ▶); Lindgren et al. (2001 ▶); Olsson et al. (2002 ▶). For related crystal structures, see: Jones & Kuś (2004 ▶); Saeed et al. (2008 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C13H16ClNO

M = 237.72

Monoclinic,

a = 14.755 (14) Å

b = 5.043 (7) Å

c = 16.818 (16) Å

β = 96.13 (6)°

V = 1244 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 173 K

0.12 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.967, T max = 0.983

3651 measured reflections

2388 independent reflections

1497 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.151

S = 1.06

2388 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021217/lh2834sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021217/lh2834Isup2.hkl

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

C13H16ClNO	F(000) = 504
Mr = 237.72	Dx = 1.269 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3651 reflections
a = 14.755 (14) Å	θ = 3.9–26.0°
b = 5.043 (7) Å	µ = 0.29 mm−1
c = 16.818 (16) Å	T = 173 K
β = 96.13 (6)°	Needle, colorless
V = 1244 (2) Å3	0.12 × 0.08 × 0.06 mm
Z = 4

Bruker APEXII CCD diffractometer	2388 independent reflections
Radiation source: fine-focus sealed tube	1497 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 26.0°, θmin = 3.9°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −18→17
Tmin = 0.967, Tmax = 0.983	k = −6→4
3651 measured reflections	l = −20→20

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0665P)2 + 0.3764P] where P = (Fo2 + 2Fc2)/3
2388 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.77571 (5)	0.29595 (19)	0.35603 (5)	0.0739 (3)
O1	0.35835 (12)	0.8003 (3)	0.37556 (11)	0.0489 (5)
N1	0.32675 (14)	0.3654 (4)	0.38965 (14)	0.0491 (6)
H1	0.3492	0.2036	0.3922	0.059*
C1	0.48155 (15)	0.4944 (5)	0.37540 (13)	0.0369 (6)
C2	0.52269 (17)	0.2853 (5)	0.41805 (15)	0.0462 (6)
H2	0.4884	0.1813	0.4512	0.055*
C3	0.61349 (18)	0.2254 (6)	0.41296 (16)	0.0529 (7)
H3	0.6419	0.0831	0.4431	0.063*
C4	0.66205 (17)	0.3746 (6)	0.36373 (15)	0.0489 (7)
C5	0.62262 (18)	0.5866 (6)	0.32108 (16)	0.0539 (7)
H5	0.6569	0.6895	0.2876	0.065*
C6	0.53255 (18)	0.6464 (5)	0.32789 (15)	0.0474 (6)
H6	0.5051	0.7938	0.2996	0.057*
C7	0.38370 (16)	0.5666 (5)	0.38013 (13)	0.0388 (6)
C8	0.22970 (16)	0.3992 (5)	0.39603 (16)	0.0484 (7)
H8	0.2181	0.5912	0.4058	0.058*
C9	0.20142 (17)	0.2430 (7)	0.46572 (16)	0.0564 (8)
H9A	0.2371	0.3025	0.5157	0.068*
H9B	0.2142	0.0524	0.4582	0.068*
C10	0.0997 (2)	0.2819 (9)	0.4724 (2)	0.0789 (11)
H10A	0.0816	0.1731	0.5171	0.095*
H10B	0.0881	0.4702	0.4845	0.095*
C11	0.04290 (19)	0.2051 (7)	0.3968 (2)	0.0735 (10)
H11A	−0.0221	0.2421	0.4022	0.088*
H11B	0.0494	0.0126	0.3875	0.088*
C12	0.0718 (2)	0.3567 (8)	0.3267 (2)	0.0819 (11)
H12A	0.0588	0.5476	0.3333	0.098*
H12B	0.0360	0.2949	0.2770	0.098*
C13	0.1742 (2)	0.3193 (7)	0.31917 (18)	0.0699 (9)
H13A	0.1864	0.1313	0.3072	0.084*
H13B	0.1920	0.4289	0.2746	0.084*

	U11	U22	U33	U12	U13	U23
Cl1	0.0443 (4)	0.0948 (7)	0.0840 (6)	0.0035 (4)	0.0128 (4)	−0.0220 (5)
O1	0.0535 (11)	0.0273 (9)	0.0662 (12)	0.0040 (8)	0.0080 (9)	0.0016 (8)
N1	0.0406 (11)	0.0278 (12)	0.0806 (15)	0.0040 (9)	0.0135 (11)	0.0015 (10)
C1	0.0413 (12)	0.0304 (12)	0.0393 (12)	−0.0013 (10)	0.0055 (10)	−0.0056 (10)
C2	0.0445 (13)	0.0408 (14)	0.0535 (15)	0.0020 (12)	0.0069 (11)	0.0053 (12)
C3	0.0475 (15)	0.0517 (17)	0.0589 (16)	0.0078 (13)	0.0025 (12)	0.0025 (14)
C4	0.0410 (13)	0.0589 (18)	0.0472 (14)	−0.0017 (13)	0.0063 (11)	−0.0165 (13)
C5	0.0550 (16)	0.0583 (18)	0.0510 (15)	−0.0079 (14)	0.0183 (13)	−0.0018 (14)
C6	0.0527 (15)	0.0415 (16)	0.0486 (14)	−0.0019 (12)	0.0086 (12)	0.0051 (12)
C7	0.0462 (14)	0.0305 (14)	0.0399 (13)	0.0006 (11)	0.0058 (10)	−0.0009 (10)
C8	0.0396 (13)	0.0292 (13)	0.0768 (18)	0.0047 (11)	0.0074 (13)	−0.0048 (13)
C9	0.0407 (14)	0.078 (2)	0.0518 (15)	0.0046 (14)	0.0100 (12)	−0.0119 (14)
C10	0.0473 (16)	0.113 (3)	0.080 (2)	0.0028 (18)	0.0212 (15)	−0.016 (2)
C11	0.0400 (15)	0.067 (2)	0.113 (3)	−0.0003 (14)	0.0070 (17)	−0.018 (2)
C12	0.0597 (19)	0.088 (3)	0.091 (2)	0.0080 (18)	−0.0240 (17)	−0.005 (2)
C13	0.0609 (18)	0.088 (2)	0.0589 (17)	0.0027 (17)	−0.0039 (14)	0.0122 (17)

Cl1—C4	1.742 (3)	C8—C13	1.510 (4)
O1—C7	1.236 (3)	C8—H8	1.0000
N1—C7	1.338 (3)	C9—C10	1.530 (4)
N1—C8	1.457 (3)	C9—H9A	0.9900
N1—H1	0.8800	C9—H9B	0.9900
C1—C2	1.379 (4)	C10—C11	1.496 (5)
C1—C6	1.386 (3)	C10—H10A	0.9900
C1—C7	1.499 (3)	C10—H10B	0.9900
C2—C3	1.385 (4)	C11—C12	1.505 (5)
C2—H2	0.9500	C11—H11A	0.9900
C3—C4	1.375 (4)	C11—H11B	0.9900
C3—H3	0.9500	C12—C13	1.541 (4)
C4—C5	1.381 (4)	C12—H12A	0.9900
C5—C6	1.379 (4)	C12—H12B	0.9900
C5—H5	0.9500	C13—H13A	0.9900
C6—H6	0.9500	C13—H13B	0.9900
C8—C9	1.508 (4)
C7—N1—C8	123.7 (2)	C8—C9—C10	110.2 (2)
C7—N1—H1	118.1	C8—C9—H9A	109.6
C8—N1—H1	118.1	C10—C9—H9A	109.6
C2—C1—C6	119.1 (2)	C8—C9—H9B	109.6
C2—C1—C7	122.1 (2)	C10—C9—H9B	109.6
C6—C1—C7	118.8 (2)	H9A—C9—H9B	108.1
C1—C2—C3	120.6 (2)	C11—C10—C9	111.7 (3)
C1—C2—H2	119.7	C11—C10—H10A	109.3
C3—C2—H2	119.7	C9—C10—H10A	109.3
C4—C3—C2	119.2 (3)	C11—C10—H10B	109.3
C4—C3—H3	120.4	C9—C10—H10B	109.3
C2—C3—H3	120.4	H10A—C10—H10B	107.9
C3—C4—C5	121.2 (3)	C10—C11—C12	110.8 (3)
C3—C4—Cl1	119.2 (2)	C10—C11—H11A	109.5
C5—C4—Cl1	119.6 (2)	C12—C11—H11A	109.5
C6—C5—C4	118.8 (2)	C10—C11—H11B	109.5
C6—C5—H5	120.6	C12—C11—H11B	109.5
C4—C5—H5	120.6	H11A—C11—H11B	108.1
C5—C6—C1	121.0 (3)	C11—C12—C13	111.3 (3)
C5—C6—H6	119.5	C11—C12—H12A	109.4
C1—C6—H6	119.5	C13—C12—H12A	109.4
O1—C7—N1	122.7 (2)	C11—C12—H12B	109.4
O1—C7—C1	121.0 (2)	C13—C12—H12B	109.4
N1—C7—C1	116.3 (2)	H12A—C12—H12B	108.0
N1—C8—C9	110.6 (2)	C8—C13—C12	110.1 (3)
N1—C8—C13	110.7 (2)	C8—C13—H13A	109.6
C9—C8—C13	110.9 (2)	C12—C13—H13A	109.6
N1—C8—H8	108.2	C8—C13—H13B	109.6
C9—C8—H8	108.2	C12—C13—H13B	109.6
C13—C8—H8	108.2	H13A—C13—H13B	108.1
C6—C1—C2—C3	−0.7 (4)	C6—C1—C7—O1	−32.8 (3)
C7—C1—C2—C3	−179.3 (2)	C2—C1—C7—N1	−34.0 (3)
C1—C2—C3—C4	−1.0 (4)	C6—C1—C7—N1	147.4 (2)
C2—C3—C4—C5	1.7 (4)	C7—N1—C8—C9	−132.2 (3)
C2—C3—C4—Cl1	−178.9 (2)	C7—N1—C8—C13	104.5 (3)
C3—C4—C5—C6	−0.6 (4)	N1—C8—C9—C10	179.5 (2)
Cl1—C4—C5—C6	−180.0 (2)	C13—C8—C9—C10	−57.3 (3)
C4—C5—C6—C1	−1.2 (4)	C8—C9—C10—C11	56.9 (4)
C2—C1—C6—C5	1.8 (4)	C9—C10—C11—C12	−56.0 (4)
C7—C1—C6—C5	−179.5 (2)	C10—C11—C12—C13	55.5 (4)
C8—N1—C7—O1	−0.3 (4)	N1—C8—C13—C12	−179.8 (3)
C8—N1—C7—C1	179.5 (2)	C9—C8—C13—C12	57.0 (3)
C2—C1—C7—O1	145.9 (2)	C11—C12—C13—C8	−56.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.06	2.901 (5)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.06	2.901 (5)	160

Symmetry code: (i) .