N-(4-Bromo­phen­yl)-3,5-dinitro­benzamide

Sohail Saeed; Naghmana Rashid; Rizwan Hussain; Wing-Tak Wong

doi:10.1107/S1600536811051464

. 2011 Dec 3;68(Pt 1):o26. doi: 10.1107/S1600536811051464

N-(4-Bromophenyl)-3,5-dinitrobenzamide

Sohail Saeed ^a,^*, Naghmana Rashid ^a, Rizwan Hussain ^b, Wing-Tak Wong ^c

PMCID: PMC3254366 PMID: 22259531

Abstract

The title molecule, C₁₃H₈BrN₃O₅, is slightly twisted, with the dihedral angle between the two benzene rings being 5.9 (1)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into one-dimensional chains running along [101]. Further stabilization of the crystal structure is provided by π–π interactions [shortest centroid–centroid distance = 3.6467 (17) Å].

Related literature

For background to the biological activity of N-substituted benzamides, their use in synthesis and for related structures, see: Saeed et al. (2011a ▶,b ▶).

Experimental

Crystal data

C₁₃H₈BrN₃O₅
M _r = 366.13
Monoclinic,
a = 7.1273 (2) Å
b = 26.6676 (7) Å
c = 7.5428 (2) Å
β = 101.652 (2)°
V = 1404.10 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.96 mm⁻¹
T = 296 K
0.56 × 0.34 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.288, T _max = 0.471
18250 measured reflections
2476 independent reflections
2007 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.108
S = 1.10
2476 reflections
204 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051464/tk5029sup1.cif

e-68-00o26-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051464/tk5029Isup2.hkl

e-68-00o26-Isup2.hkl^{(121.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811051464/tk5029Isup3.cml

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—H1N⋯O1ⁱ	0.93 (3)	1.93 (3)	2.818 (3)	159 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

Dr Wesley T.-K. Chan, Professor Z.-Y. Zhou and the Hong Kong Polytechnic University are sincerely thanked for helping to collect the X-ray data.

supplementary crystallographic information

Comment

In connection with on-going studies into N-substituted benzamides (Saeed et al., 2011a,b), we recently determined the crystal structure of 3,5-dinitro-N-(1,3-thiazol-2-yl)-benzamide monohydrate (Saeed et al., 2011a). In this paper we present the crystal structure of the title compound (I), Fig. 1.

Intermolecular N1—H1N···O1 hydrogen bonds link the molecules into 1-D chains running along [101], Table 1 and Fig. 2. The dihedral angle between the two phenyl ring planes is 5.9 (1)°. Both nitro groups are slightly twisted, 3.3 (2)° and 4.6 (2)°, respectively, from the benzene ring plane, C2—C7. There are also weak π–π interactions between neighbouring molecules, Table 2.

Experimental

To a 250 ml round flask fitted with a condenser was added ethyl 4-bromoaniline (0.1 mol), dichloromethane (15 ml) and triethylamine(0.5 ml) with magnetic stirring. 3,5-Dinitrobenzoyl chloride (0.1 mol) was added gradually. The reaction mixture was stirred at room temperature for 1 h and then refluxed for 2 h. The product precipitated as a colourless powder, which was washed three times with water and dichloromethane. Recrystallization from ethyl acetate produced the crystals of the title compound.