N-[(E)-4-(Methyl­sulfon­yl)benzyl­idene]-3-nitro­aniline

Yue-Hu Chen; Rong-Bao Ge; Hua-Jian Liu; Shao-Song Qian

doi:10.1107/S1600536811031539

. 2011 Aug 11;67(Pt 9):o2291. doi: 10.1107/S1600536811031539

N-[(E)-4-(Methylsulfonyl)benzylidene]-3-nitroaniline

Yue-Hu Chen ^a, Rong-Bao Ge ^a, Hua-Jian Liu ^a, Shao-Song Qian ^a,^*

PMCID: PMC3200823 PMID: 22064973

Abstract

In the title compound, C₁₄H₁₂N₂O₄S, the dihedral angle between the two aromatic rings is 35.65 (12)°. The crystal packing is stabilized by weak C—H⋯O hydrogen bonds and aromatic π–π ring stacking interactions [minimum ring centroid separation = 3.697 (3) Å].

Related literature

For pharmacological applications of Schiff bases, see: Venugopal & Jayashree (2008 ▶); Villar et al. (2004 ▶); Wadher et al. (2009 ▶). For similar structures, see: Qian & Cui (2009 ▶); Qian & Liu (2010 ▶). For comparative bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₂N₂O₄S
M _r = 304.32
Monoclinic,
a = 12.707 (7) Å
b = 8.669 (5) Å
c = 14.257 (8) Å
β = 114.140 (5)°
V = 1433.2 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.25 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.942, T _max = 0.951
9119 measured reflections
2525 independent reflections
1937 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.102
S = 1.02
2525 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811031539/zs2133sup1.cif

e-67-o2291-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031539/zs2133Isup2.hkl

e-67-o2291-Isup2.hkl^{(124.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811031539/zs2133Isup3.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
C14—H14C⋯O1ⁱ	0.96	2.42	3.380 (3)	178
C12—H12⋯O5ⁱⁱ	0.93	2.59	3.273 (4)	131
C6—H6⋯O2ⁱⁱⁱ	0.93	2.52	3.442 (3)	169
C5—H5⋯O4^iv	0.93	2.41	3.249 (3)	150

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

Acknowledgments

This project was sponsored by the ShanDong Province Science & Technology Innovation Foundation (People’s Republic of China).

supplementary crystallographic information

Comment

Schiff base compounds have been of great interest owing to their wide range of biological activities. They have been found to possess pharmacological activities, such as anti-cancer (Villar et al., 2004), anti-bacterial (Venugopal & Jayashree, 2008), anti-inflammatory, anti-microbial and anti-viral (Wadher et al., 2009). As an extension of our work on the structural characterization of Schiff base compounds, the crystal structure of the title compound C₁₄H₁₂N₂O₄S is reported here. In this compound (Fig. 1), all bond lengths are within normal ranges (Allen et al., 1987) and comparable with the values observed in two closely related compounds (Qian & Cui, 2009; Qian & Liu, 2010). The dihedral angle between the two aromatic rings is 35.65 (12)°. The crystal packing is stabilized by weak C—H···O hydrogen bonds (Table 1) and aromatic π-π stacking interactions [minimum ring centroid–centroid distance, 3.697 (3)Å] (Fig. 2).

Experimental

4-(Methylsulfonyl)benzaldehyde (0.184 g) and 2,6-diisopropylaniline (0.138 g) were dissolved in acetonitrile (20 ml). The mixture was stirred at room temperature for 10 min to give a clear yellow solution. After allowing the solution to evaporate in air for 5 days, yellow block-shaped crystals of the title compound were obtained.