N-(2-Chloro-4-nitro­phen­yl)-2-nitro­benzamide

Aamer Saeed; Shahid Hussain; Ulrich Flörke

doi:10.1107/S1600536808006430

. 2008 Mar 12;64(Pt 4):o705. doi: 10.1107/S1600536808006430

N-(2-Chloro-4-nitrophenyl)-2-nitrobenzamide

Aamer Saeed ^a,^*, Shahid Hussain ^a, Ulrich Flörke ^b

PMCID: PMC2961029 PMID: 21202096

Abstract

In the title compound, C₁₃H₈ClN₃O₅, the dihedral angle between the two aromatic rings is 70.74 (6)°. The nitro groups of the Cl-substituted and benzamide benzene rings are twisted by 2.6 (1) and 31.3 (2)°, respectively. The crystal packing shows intermolecular C—H⋯O hydrogen bonds that link molecules into sheets stacked along [010].

Related literature

For the biological activities of benzanilides and related compounds, see: Makino et al. (2003 ▶); Ho et al. (2002 ▶); Zhichkin et al. (2007 ▶); Jackson et al. (1994 ▶); Capdeville et al. (2002 ▶); Igawa et al. (1999 ▶). For related structures, see: Di Rienzo et al. (1980 ▶); Batsanov & Lyubchik (2003 ▶).

Experimental

Crystal data

C₁₃H₈ClN₃O₅
M _r = 321.67
Orthorhombic,
a = 7.8053 (9) Å
b = 13.8621 (17) Å
c = 24.101 (3) Å
V = 2607.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 120 (2) K
0.47 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.863, T _max = 0.956
21562 measured reflections
3111 independent reflections
2424 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.107
S = 1.04
3111 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.23 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006430/si2073sup1.cif

e-64-0o705-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006430/si2073Isup2.hkl

e-64-0o705-Isup2.hkl^{(152.8KB, 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
C13—H13A⋯O1	0.95	2.24	2.848 (2)	121
C10—H10A⋯O4ⁱ	0.95	2.35	3.246 (2)	157
C11—H11A⋯O2ⁱⁱ	0.95	2.55	3.202 (2)	126

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

AS gratefully acknowledges a research grant from Quaid-i-Azam University, Islamabad.

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. Benzanilides serve as intermediates towards benzothiadiazin-4-ones (Makino et al., 2003), benzodiazepine-2,5-diones (Ho et al., 2002), and 2,3-disubstituted 3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficacy as centroid elements of ligands that bind to a wide variety of receptor types. Thus benzanilides containing aminoalkyl groups originally designed as a peptidomimetic, have been incorporated in an Arg-Gly-Asp cyclic peptide yielding a high affinity GPIIb/IIIa ligand (Jackson et al., 1994). Imatinib is an ATP-site binding kinase inhibitor and platelet-derived growth factor receptor kinases (Capdeville et al., 2002).Benzamides have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999) The literature is full of the function of the 2-chloro-4-nitrophenyl group (CNP) and also structures of nitrobenzamide (NB) and related compounds (Di Rienzo et al., 1980; Batsanov & Lyubchik, 2003). The aim of the present work was to combine CNP and NB in a single structure which is not well known in the literature.

Geometric parameters of the title compound, C₁₃H₈ClN₃O₅, are in the usual ranges. The dihedral angle between the two aromatic rings is 70.74 (6)°. The N2 nitro group is twisted by 31.3 (2)° from the plane of the C2–C7 phenyl ring, and the N3 group 2.6 (2)° from the C8–C13 plane, respectively. The crystal packing shows intermolecular C–H···O hydrogen bonds, from the Cl-phenyl group to both nitro groups. Details are depicted in Table 1. By these hydrogen bonds molecules are linked to endless sheets that are stacked along [010]. Additionally, stacking of molecules along [100] can be recognized. The intramolecular C13–H13A···O1 interaction is a common feature for this molecule with an almost planar O1–C1–N1–C8–C13 arrangement. The corresponding torsion angles are C8–N1–C1–O1 6.7 (3)° and C1–N1–C8–C13 - 7.6 (3)°, respectively.

Experimental

2-Nitrobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 2-chloro-4-nitroaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 3 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aq 1 M HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded the title compound (84%) as white needles: IR (KBr) 3226, 1665, 1616, 1520, 1352 cm-1; 1H NMR (CDCl3, 400 MHz) ? 8.13 (d, J) 8 Hz, 1H), 7.81 (d, J) 8 Hz, 1H), 7.51 (dd, J) 8 Hz, 1H), 7.66 (dd, J) 8 Hz, 1H), 7.43 (d, J) 8 Hz, 2H), 7.36 (br s, 1H), 7.25 (d, J) 8 Hz, 1H); 13 C NMR (100 MHz) ? 164.7, 147.8, 134.6, 134.4, 132.7, 132.1, 130.3, 129.9, 129.3, 125.0. Anal. Calcd. For C₁₃H₉N₃O₅, C, 48.54; H, 2.51; Cl, 11.02; N, 13.06 found C, 48.12; H, 2.31; Cl, 11.3; N, 12.94.