3-Chloro-N-cyclo-hexyl-benzamide.

In the title mol-ecule, C(13)H(16)ClNO, the mean plane of the atoms in the -CONH- group forms a dihedral angle of 42.0 (4)° with the benzene ring plane. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds, generating C(4) chains along [100].

Related literature

For bond-length data, see: Allen (2002 ▶). For related structures, see: Garden et al. (2005 ▶); Wardell et al. (2005 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H16ClNO

M = 237.72

Orthorhombic,

a = 8.4963 (6) Å

b = 11.4891 (7) Å

c = 12.5318 (11) Å

V = 1223.29 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 173 K

0.38 × 0.22 × 0.22 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan [MULABS (Spek, 2003 ▶; Blessing, 1995 ▶)] T min = 0.898, T max = 0.939

6758 measured reflections

2737 independent reflections

2429 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.069

S = 0.98

2737 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1128 Friedel pairs

Flack parameter: 0.03 (5)

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017012/lh2817sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017012/lh2817Isup2.hkl

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

C13H16ClNO	F(000) = 504
Mr = 237.72	Dx = 1.291 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6652 reflections
a = 8.4963 (6) Å	θ = 3.4–27.7°
b = 11.4891 (7) Å	µ = 0.29 mm−1
c = 12.5318 (11) Å	T = 173 K
V = 1223.29 (16) Å3	Block, colourless
Z = 4	0.38 × 0.22 × 0.22 mm

Stoe IPDS II two-circle diffractometer	2737 independent reflections
Radiation source: fine-focus sealed tube	2429 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan [MULABS (Spek, 2003; Blessing, 1995)]	h = −11→11
Tmin = 0.898, Tmax = 0.939	k = −14→11
6758 measured reflections	l = −16→13

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030	w = 1/[σ2(Fo2) + (0.0419P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.069	(Δ/σ)max = 0.001
S = 0.98	Δρmax = 0.18 e Å−3
2737 reflections	Δρmin = −0.17 e Å−3
150 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.021 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1128 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.03 (5)

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	0.70767 (6)	1.17100 (4)	0.53982 (4)	0.04673 (13)
C1	0.54914 (14)	0.73267 (12)	0.53979 (11)	0.0203 (3)
O1	0.43572 (10)	0.67397 (9)	0.56950 (7)	0.0245 (2)
N1	0.63351 (13)	0.70808 (10)	0.45221 (9)	0.0233 (2)
H1	0.720 (2)	0.7470 (16)	0.4421 (13)	0.028 (4)*
C11	0.59541 (13)	0.84022 (13)	0.60027 (10)	0.0208 (3)
C12	0.63710 (15)	0.94177 (12)	0.54747 (11)	0.0233 (3)
H12	0.6474	0.9425	0.4720	0.028*
C13	0.66355 (15)	1.04213 (13)	0.60606 (11)	0.0260 (3)
C14	0.65300 (16)	1.04247 (14)	0.71660 (12)	0.0289 (3)
H14	0.6727	1.1117	0.7558	0.035*
C15	0.61351 (17)	0.94075 (15)	0.76869 (12)	0.0300 (3)
H15	0.6069	0.9399	0.8444	0.036*
C16	0.58335 (14)	0.83946 (14)	0.71154 (11)	0.0253 (3)
H16	0.5547	0.7701	0.7479	0.030*
C21	0.59346 (14)	0.61160 (13)	0.38088 (11)	0.0218 (3)
H21	0.4778	0.5966	0.3868	0.026*
C22	0.62972 (17)	0.64688 (13)	0.26615 (11)	0.0274 (3)
H22A	0.7431	0.6654	0.2594	0.033*
H22B	0.5690	0.7176	0.2476	0.033*
C23	0.58727 (17)	0.54859 (16)	0.18917 (12)	0.0334 (4)
H23A	0.4722	0.5353	0.1911	0.040*
H23B	0.6161	0.5717	0.1156	0.040*
C24	0.67181 (18)	0.43660 (15)	0.21786 (13)	0.0340 (3)
H24A	0.7865	0.4471	0.2080	0.041*
H24B	0.6367	0.3735	0.1696	0.041*
C25	0.6385 (2)	0.40235 (15)	0.33291 (14)	0.0373 (4)
H25A	0.7005	0.3322	0.3511	0.045*
H25B	0.5255	0.3827	0.3405	0.045*
C26	0.68006 (17)	0.50066 (13)	0.41084 (12)	0.0292 (3)
H26A	0.6508	0.4774	0.4843	0.035*
H26B	0.7950	0.5148	0.4092	0.035*

	U11	U22	U33	U12	U13	U23
Cl1	0.0806 (3)	0.02269 (18)	0.0369 (2)	−0.00841 (19)	−0.0039 (2)	0.00076 (18)
C1	0.0225 (5)	0.0208 (7)	0.0176 (5)	0.0040 (5)	−0.0026 (5)	0.0014 (6)
O1	0.0244 (4)	0.0256 (5)	0.0236 (5)	−0.0026 (4)	0.0023 (3)	0.0014 (4)
N1	0.0236 (5)	0.0234 (6)	0.0227 (5)	−0.0043 (4)	0.0028 (4)	−0.0057 (5)
C11	0.0203 (5)	0.0220 (7)	0.0202 (6)	0.0036 (5)	−0.0005 (4)	−0.0031 (6)
C12	0.0267 (5)	0.0245 (7)	0.0188 (6)	0.0028 (5)	−0.0008 (5)	−0.0020 (6)
C13	0.0304 (6)	0.0213 (7)	0.0261 (7)	0.0022 (5)	−0.0023 (5)	−0.0004 (6)
C14	0.0312 (6)	0.0291 (8)	0.0264 (7)	0.0030 (6)	−0.0031 (5)	−0.0095 (6)
C15	0.0318 (7)	0.0391 (9)	0.0190 (6)	0.0012 (6)	−0.0012 (5)	−0.0058 (6)
C16	0.0273 (6)	0.0292 (8)	0.0195 (6)	0.0012 (5)	0.0002 (5)	0.0004 (6)
C21	0.0231 (6)	0.0224 (7)	0.0199 (6)	−0.0027 (5)	−0.0008 (5)	−0.0054 (5)
C22	0.0355 (7)	0.0253 (7)	0.0214 (6)	0.0044 (6)	−0.0006 (5)	0.0001 (6)
C23	0.0360 (7)	0.0433 (10)	0.0208 (7)	0.0010 (7)	−0.0008 (5)	−0.0076 (7)
C24	0.0391 (8)	0.0306 (8)	0.0322 (7)	−0.0025 (6)	0.0058 (6)	−0.0122 (7)
C25	0.0532 (9)	0.0209 (8)	0.0377 (9)	−0.0028 (7)	0.0057 (7)	−0.0048 (7)
C26	0.0393 (7)	0.0229 (8)	0.0254 (7)	−0.0008 (6)	−0.0016 (6)	0.0018 (6)

Cl1—C13	1.7383 (16)	C21—C22	1.5253 (19)
C1—O1	1.2337 (16)	C21—H21	1.0000
C1—N1	1.3410 (17)	C22—C23	1.528 (2)
C1—C11	1.5020 (18)	C22—H22A	0.9900
N1—C21	1.4641 (17)	C22—H22B	0.9900
N1—H1	0.868 (18)	C23—C24	1.517 (3)
C11—C12	1.387 (2)	C23—H23A	0.9900
C11—C16	1.3982 (18)	C23—H23B	0.9900
C12—C13	1.385 (2)	C24—C25	1.521 (2)
C12—H12	0.9500	C24—H24A	0.9900
C13—C14	1.388 (2)	C24—H24B	0.9900
C14—C15	1.380 (2)	C25—C26	1.534 (2)
C14—H14	0.9500	C25—H25A	0.9900
C15—C16	1.390 (2)	C25—H25B	0.9900
C15—H15	0.9500	C26—H26A	0.9900
C16—H16	0.9500	C26—H26B	0.9900
C21—C26	1.519 (2)
O1—C1—N1	123.32 (13)	C21—C22—C23	110.54 (13)
O1—C1—C11	120.12 (11)	C21—C22—H22A	109.5
N1—C1—C11	116.52 (11)	C23—C22—H22A	109.5
C1—N1—C21	122.34 (11)	C21—C22—H22B	109.5
C1—N1—H1	117.6 (11)	C23—C22—H22B	109.5
C21—N1—H1	119.8 (11)	H22A—C22—H22B	108.1
C12—C11—C16	119.98 (13)	C24—C23—C22	111.43 (12)
C12—C11—C1	121.20 (11)	C24—C23—H23A	109.3
C16—C11—C1	118.62 (13)	C22—C23—H23A	109.3
C13—C12—C11	119.25 (12)	C24—C23—H23B	109.3
C13—C12—H12	120.4	C22—C23—H23B	109.3
C11—C12—H12	120.4	H23A—C23—H23B	108.0
C12—C13—C14	121.38 (14)	C23—C24—C25	110.85 (13)
C12—C13—Cl1	119.39 (11)	C23—C24—H24A	109.5
C14—C13—Cl1	119.22 (12)	C25—C24—H24A	109.5
C15—C14—C13	119.04 (14)	C23—C24—H24B	109.5
C15—C14—H14	120.5	C25—C24—H24B	109.5
C13—C14—H14	120.5	H24A—C24—H24B	108.1
C14—C15—C16	120.66 (13)	C24—C25—C26	111.71 (13)
C14—C15—H15	119.7	C24—C25—H25A	109.3
C16—C15—H15	119.7	C26—C25—H25A	109.3
C15—C16—C11	119.67 (15)	C24—C25—H25B	109.3
C15—C16—H16	120.2	C26—C25—H25B	109.3
C11—C16—H16	120.2	H25A—C25—H25B	107.9
N1—C21—C26	111.83 (11)	C21—C26—C25	110.41 (13)
N1—C21—C22	109.11 (11)	C21—C26—H26A	109.6
C26—C21—C22	110.99 (11)	C25—C26—H26A	109.6
N1—C21—H21	108.3	C21—C26—H26B	109.6
C26—C21—H21	108.3	C25—C26—H26B	109.6
C22—C21—H21	108.3	H26A—C26—H26B	108.1
O1—C1—N1—C21	2.9 (2)	C14—C15—C16—C11	0.9 (2)
C11—C1—N1—C21	−174.88 (11)	C12—C11—C16—C15	−0.08 (19)
O1—C1—C11—C12	−137.24 (12)	C1—C11—C16—C15	−174.93 (12)
N1—C1—C11—C12	40.62 (17)	C1—N1—C21—C26	−92.52 (14)
O1—C1—C11—C16	37.55 (17)	C1—N1—C21—C22	144.31 (12)
N1—C1—C11—C16	−144.60 (12)	N1—C21—C22—C23	−179.27 (11)
C16—C11—C12—C13	−1.17 (19)	C26—C21—C22—C23	57.06 (15)
C1—C11—C12—C13	173.54 (11)	C21—C22—C23—C24	−56.47 (16)
C11—C12—C13—C14	1.6 (2)	C22—C23—C24—C25	55.47 (17)
C11—C12—C13—Cl1	−177.30 (9)	C23—C24—C25—C26	−55.16 (18)
C12—C13—C14—C15	−0.8 (2)	N1—C21—C26—C25	−178.62 (12)
Cl1—C13—C14—C15	178.16 (10)	C22—C21—C26—C25	−56.52 (15)
C13—C14—C15—C16	−0.5 (2)	C24—C25—C26—C21	55.74 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.868 (18)	2.052 (18)	2.9161 (15)	173.3 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.868 (18)	2.052 (18)	2.9161 (15)	173.3 (16)

Symmetry code: (i) .