N-Butyl-4-chloro­benzamide

Aamer Saeed; Rasheed Ahmad Khera; Naeem Abbas; Jim Simpson; Roderick G Stanley

doi:10.1107/S1600536808036313

. 2008 Nov 13;64(Pt 12):o2322–o2323. doi: 10.1107/S1600536808036313

N-Butyl-4-chlorobenzamide

Aamer Saeed ^a,^*, Rasheed Ahmad Khera ^a, Naeem Abbas ^a, Jim Simpson ^b, Roderick G Stanley ^b

PMCID: PMC2960128 PMID: 21581298

Abstract

In the title benzamide derivative, C₁₁H₁₄ClNO, the chlorobenzene and butylamine 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 molecules in rows along a. Short intermolecular Cl⋯Cl interactions [3.4225 (5) Å] link these rows into sheets in the ac plane. Additional weak C—H⋯O and C—H⋯π interactions 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 _r = 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
Δρ_max = 0.43 e Å⁻³
Δρ_min = −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 ▶).

Supplementary Material

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

e-64-o2322-sup1.cif^{(16.1KB, cif)}

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

e-64-o2322-Isup2.hkl^{(168.9KB, hkl)}

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—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

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

Acknowledgments

NA gratefully acknowledges financial support for a PhD programme by the Higher Education Commission of Pakistan. We also thank the University of Otago for purchase of the diffractometer.

supplementary crystallographic information

Comment

The benzanilide core is present in compounds with such a wide range of biological activities that it has been called a privileged structure. N-substituted benzamides are well known anticancer compounds and the mechanism of action for N-substituted benzamide-induced apoptosis has been studied, using declopramide as a lead compound (Olsson et al., 2002). N-substituted benzamides inhibit the activity of nuclear factor- B and nuclear factor of activated T cells activity while inducing activator protein 1 activity in T lymphocytes (Lindgren et al., 2001). Various N-substituted benzamides exhibit potent antiemetic activity (Vega-noverola et al., 1989), while heterocyclic analogs of benzanilide derivatives are potassium channel activators (Calderone et al., 2006). o-Aryloxylation of N-substituted benzamides induced by the copper(II)/trimethylamine N-oxide system has been studied (Reinaud et al., 1991). N-Alkylated 2-nitrobenzamides are intermediates in the synthesis of dibenzo[b,e][1,4]diazepines (Zhichkin et al., 2007) and N-Acyl-2-nitrobenzamides are precursors of 2,3-disubstitued 3H-quinazoline-4-ones (Beccalli et al., 2005). A one-pot conversion of 2-nitro-n-arylbenzamides to 2,3-dihydro-1H-quinazoline-4-ones has also been reported (Yoo et al., 2005). The anomalous dual fluorescence of benzanilides has been assigned to the two lowest benzanilide singlet states (Lewis & Long, 1998)

As part of our work on the structure of benzanildes and related compounds, we report here the structure of the title benzamide derivative, I, Fig. 1. The C1···C7/Cl system is planar with a maximum deviation of 0.0161 (7) Å from the least squares plane. The carbonyl oxygen atom O1 is displaced by 0.6102 (10) Å from this plane. The butylamine N1/C8···C11 fragment is also planar, maximum deviation 0.0365 (7) Å for C9. The dihedral angle between these two planes is 2.54 (9) °. Bond distances within the molecule are normal (Allen et al., 1987) and similar to those found in the structures of related 4-chlorobenzamide derivatives (Saeed et al., 2008, Hempel et al., 2005).

In the crystal structure N1—HN1···O1 hydrogen bonds, Table 1, link molecules into rows along a. Cl1···Cl1 interactions at 3.4225 (5) Å bridge these rows to form sheets in the ac plane, Fig. 2. The sheets are interconnected by weak C3—H3···O1 hydrogen bonds and C8—H8···π interactions involving the C2···C7 benzene ring to generate a three dimensional network, Fig. 3.

Experimental

2-Fluorobenzoyl chloride (1 mmol) in CHCl₃ was treated with cyclohexyl amine (3.5 mmol) under a nitrogen atmosphere at reflux for 5 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with 1 M aq HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in ethanol afforded the title compound (79 %) as white needles: Anal. calcd. for C₁₁H₁₄ClNO: C 62.41, H 6.67, N 6.62%; found: C 62.34, H 7.16, N 6.57%.