3,5-Dinitro-N-(4-nitro­phen­yl)benzamide

Yuehong Ren; Yu Zuo; Yonggang Xiang; Ruitao Zhu

doi:10.1107/S1600536810045915

. 2010 Nov 13;66(Pt 12):o3158. doi: 10.1107/S1600536810045915

3,5-Dinitro-N-(4-nitrophenyl)benzamide

Yuehong Ren ^a, Yu Zuo ^a, Yonggang Xiang ^a, Ruitao Zhu ^a,^*

PMCID: PMC3011508 PMID: 21589455

Abstract

In the title molecule, C₁₃H₈N₄O₇, the amide fragment has an anti configuration. The mean planes of the two benzene rings form a dihedral angle of 7.78 (4)°. The mean planes of the three nitro groups are twisted by 6.82 (3), 5.01 (4) and 18.94 (7)° with respect to the benzene rings to which they are attached. In the crystal, molecules are linked by weak intermolecular N—H⋯O hydrogen bonds into chains along [100].

Related literature

For background to the biological activity of N-substituted benzamides and their use in synthesis, see: Saeed et al. (2010 ▶). For related structures, see: Raza et al. (2010 ▶); Gowda et al. (2003 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₃H₈N₄O₇
M _r = 332.23
Monoclinic,
a = 7.8999 (9) Å
b = 8.019 (1) Å
c = 21.111 (2) Å
β = 94.285 (1)°
V = 1333.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 298 K
0.48 × 0.38 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.937, T _max = 0.980
6462 measured reflections
2361 independent reflections
1419 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.127
S = 1.01
2361 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810045915/lh5155sup1.cif

e-66-o3158-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045915/lh5155Isup2.hkl

e-66-o3158-Isup2.hkl^{(116KB, 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—H1⋯O2ⁱ	0.86	2.52	3.280 (3)	147

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge the University Technology Development Project in Shanxi Province (20101116).

supplementary crystallographic information

Comment

N-substituted benzamides have numerous pharmaceutical and synthetic application (Saeed et al. 2010). In this paper, we report the structure of the title compound (I). The molecular structure of (I) is shown in Fig. 1. The bond lengths are within normal ranges (Allen et al. 1987). The amide N—H and C═O bonds in the molecule comprising the crystallographic asymmetric unit are trans to each other and similar to those observed in 2-Hydroxy-N-(3-nitrophenyl)benzamide (Raza et al. 2010) and 2-chloro-N-(phenyl)-benzamide (NP2CBA) (Gowda et al., 2003). The mean planes of the two benzene rings form a dihedral angle of 7.78 (4)°. The mean planes of the three nitro groups are twisted by 6.82 (3)°, 5.01 (4)° and 18.94 (7)° with respect to the benzene rings to which they are attached. In the crystal structure, molecules are linked by weak intermolecular N-H···O hydrogen bonds in chains along [100] (see Fig. 2).

Experimental

3,5-Dinitrobenzoyl chloride (1.15 g, 5 mmol) dissolved in tetrahydrofuran (10 ml) was added to 4-nitroaniline (0.69 g, 5 mmol) dissolved in tetrahydrofuran (5 ml), the reaction mixture was refluxed for 2 h, then cooled to ambient temperature and filtered to remove the tetrahydrofuran. The precipitate was dissolved in methanol/tetrahydrofuran/ethyl acetate (1:1:1) and the solution was allowed to stand for a few days at ambient temperature, after which time colorless plates of the title compound suitable for X-ray diffraction were obtaind.