2,4-Dichloro-N-cyclo-hexyl-benzamide.

In the title mol-ecule, C(13)H(15)Cl(2)NO, the cyclohexane ring adopts a chair conformation. The aromatic ring plane is oriented with respect to the N/O/C plane at a dihedral angle of 51.88 (7)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into infinite chains along the [010] direction.

Related literature

For related literature, see: Makino et al. (2001 ▶, 2003 ▶); Ho et al. (2002 ▶); Zhichkin et al. (2007 ▶); Jackson et al. (1994 ▶); Capdeville et al. (2002 ▶); Manley et al. (2002 ▶); Igawa et al. (1999 ▶); Jones & Kuś (2004 ▶). For ring conformation puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C13H15Cl2NO

M = 272.16

Monoclinic,

a = 26.135 (3) Å

b = 4.9144 (6) Å

c = 20.449 (2) Å

β = 90.167 (3)°

V = 2626.4 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.48 mm−1

T = 120 (2) K

0.48 × 0.17 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.803, T max = 0.945

10950 measured reflections

3141 independent reflections

2389 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.110

S = 1.02

3141 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008131/hk2439sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008131/hk2439Isup2.hkl

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

C13H15Cl2NO	F000 = 1136
Mr = 272.16	Dx = 1.377 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 978 reflections
a = 26.135 (3) Å	θ = 2.5–25.9º
b = 4.9144 (6) Å	µ = 0.48 mm−1
c = 20.449 (2) Å	T = 120 (2) K
β = 90.167 (3)º	Prism, colorless
V = 2626.4 (5) Å3	0.48 × 0.17 × 0.12 mm
Z = 8

Bruker SMART APEX diffractometer	3141 independent reflections
Radiation source: sealed tube	2389 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 120(2) K	θmax = 27.9º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −34→34
Tmin = 0.803, Tmax = 0.945	k = −6→6
10950 measured reflections	l = −26→26

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0561P)2 + 0.7836P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3141 reflections	Δρmax = 0.33 e Å−3
154 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 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.

	x	y	z	Uiso*/Ueq
Cl1	0.55602 (2)	0.84379 (11)	0.19724 (2)	0.03406 (16)
Cl2	0.683870 (19)	0.21813 (13)	0.05939 (3)	0.04287 (18)
O1	0.45551 (5)	0.8154 (2)	0.11531 (7)	0.0276 (3)
N1	0.43595 (6)	0.3718 (3)	0.12891 (8)	0.0251 (4)
H1B	0.4481	0.2049	0.1303	0.030*
C1	0.38119 (6)	0.4124 (4)	0.13939 (10)	0.0246 (4)
H1A	0.3743	0.6126	0.1403	0.029*
C2	0.35016 (7)	0.2882 (5)	0.08417 (9)	0.0309 (5)
H2A	0.3568	0.0901	0.0821	0.037*
H2B	0.3607	0.3698	0.0421	0.037*
C3	0.29284 (8)	0.3379 (5)	0.09487 (10)	0.0375 (5)
H3A	0.2858	0.5356	0.0927	0.045*
H3B	0.2731	0.2480	0.0595	0.045*
C4	0.27550 (7)	0.2290 (5)	0.16035 (10)	0.0333 (5)
H4A	0.2780	0.0280	0.1602	0.040*
H4B	0.2392	0.2784	0.1673	0.040*
C5	0.30768 (8)	0.3422 (5)	0.21592 (10)	0.0382 (5)
H5A	0.2973	0.2548	0.2575	0.046*
H5B	0.3014	0.5401	0.2200	0.046*
C6	0.36460 (7)	0.2927 (5)	0.20447 (9)	0.0317 (5)
H6A	0.3847	0.3769	0.2403	0.038*
H6B	0.3715	0.0946	0.2048	0.038*
C7	0.46841 (7)	0.5748 (4)	0.11741 (8)	0.0193 (4)
C8	0.52252 (6)	0.4894 (3)	0.10407 (8)	0.0179 (4)
C9	0.56448 (7)	0.6043 (4)	0.13615 (8)	0.0214 (4)
C10	0.61389 (7)	0.5236 (4)	0.12231 (9)	0.0256 (4)
H10A	0.6421	0.6031	0.1447	0.031*
C11	0.62169 (7)	0.3258 (4)	0.07559 (9)	0.0256 (4)
C12	0.58138 (7)	0.2087 (4)	0.04197 (9)	0.0247 (4)
H12A	0.5873	0.0740	0.0096	0.030*
C13	0.53219 (7)	0.2924 (4)	0.05662 (9)	0.0213 (4)
H13A	0.5042	0.2134	0.0337	0.026*

	U11	U22	U33	U12	U13	U23
Cl1	0.0376 (3)	0.0338 (3)	0.0307 (3)	−0.0036 (2)	−0.0058 (2)	−0.0119 (2)
Cl2	0.0182 (2)	0.0630 (4)	0.0474 (3)	0.0106 (2)	0.0028 (2)	0.0024 (3)
O1	0.0274 (7)	0.0119 (7)	0.0436 (8)	0.0027 (5)	0.0016 (6)	0.0005 (6)
N1	0.0181 (8)	0.0111 (7)	0.0463 (10)	0.0031 (6)	0.0046 (7)	−0.0003 (7)
C1	0.0170 (8)	0.0140 (9)	0.0428 (11)	0.0028 (7)	0.0061 (8)	0.0019 (8)
C2	0.0229 (10)	0.0470 (13)	0.0229 (10)	0.0073 (9)	0.0017 (8)	0.0067 (9)
C3	0.0219 (10)	0.0570 (15)	0.0335 (11)	0.0077 (10)	−0.0015 (9)	0.0059 (10)
C4	0.0191 (9)	0.0394 (13)	0.0413 (12)	−0.0002 (9)	0.0046 (8)	0.0033 (10)
C5	0.0295 (11)	0.0534 (15)	0.0318 (11)	0.0005 (10)	0.0091 (9)	−0.0050 (10)
C6	0.0243 (10)	0.0472 (14)	0.0237 (9)	−0.0002 (9)	−0.0003 (8)	−0.0091 (9)
C7	0.0220 (9)	0.0160 (9)	0.0199 (8)	0.0007 (7)	−0.0008 (7)	−0.0017 (7)
C8	0.0202 (8)	0.0142 (8)	0.0195 (8)	0.0000 (7)	0.0002 (7)	0.0041 (7)
C9	0.0254 (9)	0.0178 (9)	0.0209 (8)	−0.0027 (7)	−0.0007 (7)	0.0025 (7)
C10	0.0207 (9)	0.0320 (11)	0.0242 (9)	−0.0058 (8)	−0.0045 (7)	0.0053 (8)
C11	0.0170 (9)	0.0342 (11)	0.0256 (9)	0.0044 (8)	0.0023 (7)	0.0070 (8)
C12	0.0239 (9)	0.0269 (11)	0.0235 (9)	0.0047 (8)	0.0016 (7)	0.0003 (8)
C13	0.0190 (9)	0.0206 (10)	0.0244 (9)	0.0006 (7)	−0.0021 (7)	−0.0008 (7)

Cl1—C9	1.7310 (19)	C4—H4B	0.9900
Cl2—C11	1.7419 (19)	C5—C6	1.526 (3)
O1—C7	1.231 (2)	C5—H5A	0.9900
N1—C7	1.331 (2)	C5—H5B	0.9900
N1—C1	1.461 (2)	C6—H6A	0.9900
N1—H1B	0.8800	C6—H6B	0.9900
C1—C2	1.517 (3)	C7—C8	1.501 (2)
C1—C6	1.519 (3)	C8—C13	1.394 (2)
C1—H1A	1.0000	C8—C9	1.396 (2)
C2—C3	1.534 (3)	C9—C10	1.381 (3)
C2—H2A	0.9900	C10—C11	1.378 (3)
C2—H2B	0.9900	C10—H10A	0.9500
C3—C4	1.513 (3)	C11—C12	1.382 (3)
C3—H3A	0.9900	C12—C13	1.383 (3)
C3—H3B	0.9900	C12—H12A	0.9500
C4—C5	1.518 (3)	C13—H13A	0.9500
C4—H4A	0.9900
C7—N1—C1	123.28 (15)	C4—C5—H5B	109.3
C7—N1—H1B	118.4	C6—C5—H5B	109.3
C1—N1—H1B	118.4	H5A—C5—H5B	108.0
N1—C1—C2	110.95 (16)	C1—C6—C5	110.70 (17)
N1—C1—C6	110.96 (16)	C1—C6—H6A	109.5
C2—C1—C6	110.05 (15)	C5—C6—H6A	109.5
N1—C1—H1A	108.3	C1—C6—H6B	109.5
C2—C1—H1A	108.3	C5—C6—H6B	109.5
C6—C1—H1A	108.3	H6A—C6—H6B	108.1
C1—C2—C3	110.49 (17)	O1—C7—N1	123.48 (16)
C1—C2—H2A	109.6	O1—C7—C8	121.36 (16)
C3—C2—H2A	109.6	N1—C7—C8	115.11 (15)
C1—C2—H2B	109.6	C13—C8—C9	117.66 (16)
C3—C2—H2B	109.6	C13—C8—C7	119.55 (15)
H2A—C2—H2B	108.1	C9—C8—C7	122.76 (15)
C4—C3—C2	111.41 (16)	C10—C9—C8	121.43 (17)
C4—C3—H3A	109.3	C10—C9—Cl1	117.70 (14)
C2—C3—H3A	109.3	C8—C9—Cl1	120.82 (14)
C4—C3—H3B	109.3	C11—C10—C9	119.00 (17)
C2—C3—H3B	109.3	C11—C10—H10A	120.5
H3A—C3—H3B	108.0	C9—C10—H10A	120.5
C3—C4—C5	111.50 (18)	C10—C11—C12	121.64 (17)
C3—C4—H4A	109.3	C10—C11—Cl2	119.08 (14)
C5—C4—H4A	109.3	C12—C11—Cl2	119.28 (15)
C3—C4—H4B	109.3	C11—C12—C13	118.43 (18)
C5—C4—H4B	109.3	C11—C12—H12A	120.8
H4A—C4—H4B	108.0	C13—C12—H12A	120.8
C4—C5—C6	111.40 (17)	C12—C13—C8	121.83 (17)
C4—C5—H5A	109.3	C12—C13—H13A	119.1
C6—C5—H5A	109.3	C8—C13—H13A	119.1
C7—N1—C1—C2	113.7 (2)	N1—C7—C8—C9	−130.16 (18)
C7—N1—C1—C6	−123.64 (19)	C13—C8—C9—C10	−1.0 (3)
N1—C1—C2—C3	−178.66 (16)	C7—C8—C9—C10	−179.29 (16)
C6—C1—C2—C3	58.1 (2)	C13—C8—C9—Cl1	−178.28 (13)
C1—C2—C3—C4	−56.3 (2)	C7—C8—C9—Cl1	3.4 (2)
C2—C3—C4—C5	54.1 (3)	C8—C9—C10—C11	0.2 (3)
C3—C4—C5—C6	−54.1 (3)	Cl1—C9—C10—C11	177.62 (14)
N1—C1—C6—C5	178.53 (16)	C9—C10—C11—C12	0.6 (3)
C2—C1—C6—C5	−58.3 (2)	C9—C10—C11—Cl2	−178.55 (14)
C4—C5—C6—C1	56.2 (2)	C10—C11—C12—C13	−0.7 (3)
C1—N1—C7—O1	0.9 (3)	Cl2—C11—C12—C13	178.49 (14)
C1—N1—C7—C8	−176.58 (16)	C11—C12—C13—C8	−0.1 (3)
O1—C7—C8—C13	−126.00 (18)	C9—C8—C13—C12	0.9 (3)
N1—C7—C8—C13	51.5 (2)	C7—C8—C13—C12	179.29 (17)
O1—C7—C8—C9	52.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1i	0.88	1.95	2.796 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1i	0.88	1.95	2.796 (3)	161

Symmetry code: (i) .