N-Butyl-4-chloro-benzamide.

In the title benzamide derivative, C(11)H(14)ClNO, the chloro-benzene and butyl-amine groups are each planar, with mean deviations from the planes of 0.013 and 0.030 Å, respectively, and a dihedral angle of 2.54 (9)° between the two planes. In the crystal structure, N-H⋯O hydrogen bonds link mol-ecules in rows along a. Short inter-molecular Cl⋯Cl inter-actions [3.4225 (5) Å] link these rows into sheets in the ac plane. Additional weak C-H⋯O and C-H⋯π inter-actions generate a three-dimensional network.

Related literature

For details of the biological activity of benzanilides, see: Olsson et al., (2002 ▶); Lindgren et al. (2001 ▶); Calderone et al. (2006 ▶). For the use of benzamides in organic synthesis, see: Reinaud et al. (1991 ▶); Zhichkin et al. (2007 ▶); Beccalli et al. (2005 ▶); For the fluorescence properties of benzanilides, see: Lewis & Long (1998 ▶). For related structures see: Saeed et al. (2008 ▶); Hempel et al. (2005 ▶). For reference structural data, see: Allen et al. (1987 ▶). For related literature, see: Vega-Noverola et al. (1989 ▶); Yoo et al. (2005 ▶).

Experimental

Crystal data

C11H14ClNO

M = 211.68

Triclinic,

a = 5.1702 (4) Å

b = 7.8979 (5) Å

c = 13.2978 (9) Å

α = 89.275 (3)°

β = 84.863 (4)°

γ = 77.165 (4)°

V = 527.29 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 81 (2) K

0.42 × 0.30 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.820, T max = 0.974

6632 measured reflections

3445 independent reflections

3050 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.04

3445 reflections

132 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036313/sg2272sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036313/sg2272Isup2.hkl

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

C11H14ClNO	Z = 2
Mr = 211.68	F000 = 224
Triclinic, P1	Dx = 1.333 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.1702 (4) Å	Cell parameters from 3494 reflections
b = 7.8979 (5) Å	θ = 5.3–66.2º
c = 13.2978 (9) Å	µ = 0.33 mm−1
α = 89.275 (3)º	T = 81 (2) K
β = 84.863 (4)º	Irregular fragment, colourless
γ = 77.165 (4)º	0.42 × 0.30 × 0.08 mm
V = 527.29 (6) Å3

Bruker APEXII CCD area-detector diffractometer	3445 independent reflections
Radiation source: fine-focus sealed tube	3050 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 81(2) K	θmax = 33.1º
ω scans	θmin = 3.1º
Absorption correction: multi-scan(SADABS; Bruker, 2006)	h = −7→6
Tmin = 0.820, Tmax = 0.974	k = −11→11
6632 measured reflections	l = −20→20

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) = 0.090	w = 1/[σ2(Fo2) + (0.0471P)2 + 0.125P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.002
3445 reflections	Δρmax = 0.43 e Å−3
132 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N1	0.51637 (16)	0.82511 (10)	−0.10915 (6)	0.01587 (15)
HN1	0.662 (3)	0.8260 (18)	−0.0876 (11)	0.026 (3)*
C1	0.31476 (17)	0.79695 (10)	−0.04475 (6)	0.01281 (15)
O1	0.08420 (13)	0.81551 (8)	−0.06861 (5)	0.01616 (14)
C2	0.38267 (17)	0.73835 (10)	0.05917 (6)	0.01257 (15)
C3	0.18549 (19)	0.78474 (11)	0.13885 (7)	0.01611 (17)
H3	0.0169	0.8545	0.1262	0.019*
C4	0.2331 (2)	0.73001 (12)	0.23650 (7)	0.01847 (18)
H4	0.0995	0.7631	0.2908	0.022*
C5	0.4800 (2)	0.62579 (11)	0.25329 (7)	0.01667 (17)
Cl1	0.54360 (5)	0.55693 (3)	0.375283 (17)	0.02530 (8)
C6	0.67765 (19)	0.57568 (12)	0.17528 (7)	0.01740 (17)
H6	0.8439	0.5027	0.1879	0.021*
C7	0.62886 (18)	0.63406 (11)	0.07801 (7)	0.01532 (16)
H7	0.7642	0.6026	0.0241	0.018*
C8	0.47533 (19)	0.87979 (13)	−0.21289 (7)	0.01730 (17)
H8A	0.4281	1.0082	−0.2152	0.021*
H8B	0.3242	0.8363	−0.2352	0.021*
C9	0.72100 (18)	0.81319 (12)	−0.28494 (7)	0.01526 (16)
H9A	0.7664	0.6847	−0.2840	0.018*
H9B	0.8733	0.8549	−0.2623	0.018*
C10	0.67469 (19)	0.87506 (12)	−0.39261 (7)	0.01705 (17)
H10A	0.5112	0.8435	−0.4123	0.020*
H10B	0.6458	1.0032	−0.3943	0.020*
C11	0.9070 (2)	0.79692 (14)	−0.46899 (8)	0.02213 (19)
H11A	1.0696	0.8277	−0.4500	0.033*
H11B	0.8691	0.8425	−0.5363	0.033*
H11C	0.9317	0.6703	−0.4698	0.033*

	U11	U22	U33	U12	U13	U23
N1	0.0106 (3)	0.0251 (4)	0.0134 (3)	−0.0064 (3)	−0.0033 (3)	0.0048 (3)
C1	0.0120 (4)	0.0133 (3)	0.0131 (4)	−0.0024 (3)	−0.0018 (3)	0.0006 (3)
O1	0.0097 (3)	0.0217 (3)	0.0170 (3)	−0.0028 (2)	−0.0029 (2)	0.0024 (2)
C2	0.0115 (4)	0.0138 (3)	0.0131 (4)	−0.0038 (3)	−0.0025 (3)	0.0013 (3)
C3	0.0132 (4)	0.0188 (4)	0.0154 (4)	−0.0017 (3)	−0.0005 (3)	0.0009 (3)
C4	0.0185 (4)	0.0224 (4)	0.0140 (4)	−0.0043 (3)	0.0006 (3)	0.0006 (3)
C5	0.0213 (4)	0.0170 (4)	0.0138 (4)	−0.0074 (3)	−0.0055 (3)	0.0036 (3)
Cl1	0.03326 (15)	0.02986 (13)	0.01517 (12)	−0.00986 (10)	−0.00874 (9)	0.00705 (8)
C6	0.0160 (4)	0.0180 (4)	0.0184 (4)	−0.0030 (3)	−0.0058 (3)	0.0038 (3)
C7	0.0117 (4)	0.0177 (4)	0.0159 (4)	−0.0019 (3)	−0.0015 (3)	0.0016 (3)
C8	0.0121 (4)	0.0261 (4)	0.0137 (4)	−0.0040 (3)	−0.0022 (3)	0.0059 (3)
C9	0.0115 (4)	0.0202 (4)	0.0143 (4)	−0.0034 (3)	−0.0028 (3)	0.0018 (3)
C10	0.0138 (4)	0.0230 (4)	0.0139 (4)	−0.0032 (3)	−0.0020 (3)	0.0029 (3)
C11	0.0185 (5)	0.0300 (5)	0.0170 (4)	−0.0043 (4)	0.0006 (3)	−0.0014 (3)

N1—C1	1.3446 (12)	C6—H6	0.9500
N1—C8	1.4598 (11)	C7—H7	0.9500
N1—HN1	0.831 (15)	C8—C9	1.5185 (13)
C1—O1	1.2378 (11)	C8—H8A	0.9900
C1—C2	1.4984 (12)	C8—H8B	0.9900
C2—C3	1.3952 (12)	C9—C10	1.5290 (12)
C2—C7	1.3955 (12)	C9—H9A	0.9900
C3—C4	1.3891 (13)	C9—H9B	0.9900
C3—H3	0.9500	C10—C11	1.5242 (13)
C4—C5	1.3918 (13)	C10—H10A	0.9900
C4—H4	0.9500	C10—H10B	0.9900
C5—C6	1.3848 (14)	C11—H11A	0.9800
C5—Cl1	1.7405 (9)	C11—H11B	0.9800
C6—C7	1.3931 (12)	C11—H11C	0.9800
C1—N1—C8	121.48 (8)	N1—C8—C9	112.18 (7)
C1—N1—HN1	119.5 (10)	N1—C8—H8A	109.2
C8—N1—HN1	118.4 (10)	C9—C8—H8A	109.2
O1—C1—N1	122.89 (8)	N1—C8—H8B	109.2
O1—C1—C2	120.60 (8)	C9—C8—H8B	109.2
N1—C1—C2	116.51 (8)	H8A—C8—H8B	107.9
C3—C2—C7	119.40 (8)	C8—C9—C10	111.15 (7)
C3—C2—C1	117.87 (8)	C8—C9—H9A	109.4
C7—C2—C1	122.67 (8)	C10—C9—H9A	109.4
C4—C3—C2	120.71 (8)	C8—C9—H9B	109.4
C4—C3—H3	119.6	C10—C9—H9B	109.4
C2—C3—H3	119.6	H9A—C9—H9B	108.0
C3—C4—C5	118.78 (9)	C11—C10—C9	112.75 (8)
C3—C4—H4	120.6	C11—C10—H10A	109.0
C5—C4—H4	120.6	C9—C10—H10A	109.0
C6—C5—C4	121.65 (8)	C11—C10—H10B	109.0
C6—C5—Cl1	118.96 (7)	C9—C10—H10B	109.0
C4—C5—Cl1	119.39 (7)	H10A—C10—H10B	107.8
C5—C6—C7	118.95 (8)	C10—C11—H11A	109.5
C5—C6—H6	120.5	C10—C11—H11B	109.5
C7—C6—H6	120.5	H11A—C11—H11B	109.5
C6—C7—C2	120.49 (9)	C10—C11—H11C	109.5
C6—C7—H7	119.8	H11A—C11—H11C	109.5
C2—C7—H7	119.8	H11B—C11—H11C	109.5
C8—N1—C1—O1	−0.14 (13)	C3—C4—C5—Cl1	179.68 (7)
C8—N1—C1—C2	179.00 (8)	C4—C5—C6—C7	1.22 (14)
O1—C1—C2—C3	−30.72 (12)	Cl1—C5—C6—C7	−178.56 (7)
N1—C1—C2—C3	150.11 (8)	C5—C6—C7—C2	−1.35 (13)
O1—C1—C2—C7	146.41 (9)	C3—C2—C7—C6	0.37 (13)
N1—C1—C2—C7	−32.76 (12)	C1—C2—C7—C6	−176.72 (8)
C7—C2—C3—C4	0.79 (13)	C1—N1—C8—C9	−149.00 (8)
C1—C2—C3—C4	178.01 (8)	N1—C8—C9—C10	−178.91 (7)
C2—C3—C4—C5	−0.92 (14)	C8—C9—C10—C11	−174.52 (8)
C3—C4—C5—C6	−0.10 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1i	0.831 (15)	2.203 (15)	3.0164 (10)	166.3 (13)
C3—H3···O1ii	0.95	2.66	3.3146 (11)	127
C8—H8A···Cg1iii	0.99	2.84	3.697 (16)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1i	0.831 (15)	2.203 (15)	3.0164 (10)	166.3 (13)
C3—H3⋯O1ii	0.95	2.66	3.3146 (11)	127
C8—H8A⋯Cg1iii	0.99	2.84	3.697 (16)	145

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C2–C7 benzene ring.