4-[(E)-(3-Chloro-4-methyl­phen­yl)imino­meth­yl]-2-methoxy-3-nitro­phenyl acetate

Deng-Cheng Su; Feng-Ting Wang; Cheng-Gong Mao; Shao-Song Qian

doi:10.1107/S1600536811055590

. 2012 Jan 7;68(Pt 2):o303. doi: 10.1107/S1600536811055590

4-[(E)-(3-Chloro-4-methylphenyl)iminomethyl]-2-methoxy-3-nitrophenyl acetate

Deng-Cheng Su ^a, Feng-Ting Wang ^a, Cheng-Gong Mao ^a, Shao-Song Qian ^a,^*

PMCID: PMC3274996 PMID: 22346941

Abstract

The title compound, C₁₇H₁₅ClN₂O₅, displays a trans-configuration with respect to the C=N double bond. The molecule is twisted, the dihedral angle between the mean planes of the two benzene rings being 18.70 (12)°. The nitro, methoxy and acetyl groups are oriented at 80.70 (11), 35.2 (2) and 72.35 (10)°, respectively, to the benzene ring to which they are bonded. The crystal structure is stabilized by weak C—H⋯O hydrogen-bonding contacts.

Related literature

For background to Schiff bases in coordination chemistry, see: Bhatia et al. (1981 ▶); Costamagna et al. (1992 ▶). For a related structure, see: Qian & Liu (2010 ▶).

Experimental

Crystal data

C₁₇H₁₅ClN₂O₅
M _r = 362.76
Triclinic,
a = 7.035 (6) Å
b = 7.672 (6) Å
c = 17.272 (14) Å
α = 83.477 (8)°
β = 84.994 (8)°
γ = 66.697 (7)°
V = 849.7 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.26 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.936, T _max = 0.948
5579 measured reflections
3083 independent reflections
2207 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.122
S = 1.05
3083 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 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/S1600536811055590/pv2498sup1.cif

e-68-0o303-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055590/pv2498Isup2.hkl

e-68-0o303-Isup2.hkl^{(151.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811055590/pv2498Isup3.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
C12—H12⋯O1ⁱ	0.93	2.58	3.431 (3)	153

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Schiff bases play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures (Costamagna et al., 1992; Bhatia et al., 1981). As an extension of work on the structural characterization of Schiff base compounds, we report the synthesis and crystal structure of the title compound in this article.

The title compound (Fig. 1) assumes an E conformation about the C═N double bond. The molecule is twisted, with the dihedral angle between the two benzene rings being 18.70 (12)°. The nitro (N2/O1/O2), methoxy (O3/C15) and ethanone (O4/O5/C16/C17) groups are oriented with respect to the benzene ring (C8–C13) to which they are bonded, at 80.70 (11), 35.2 (2) and 72.35 (10) °, respectively. The crystal structure is stabilized by π-π interactions [centroid-centroid distance = 3.886 (4) Å ] and weak C12—H12···O1 hydrogen bonding contacts.

The bond lengths and bond angles in the title compound are comparable to the corresponding bond lengths and bond angles observed in a closely related compound (Qian & Liu, 2010).

Experimental

4-Formyl-2-methoxy-3-nitrophenyl acetate (0.0995 g) and 3-chloro-4-methylaniline (0.0706 g) were dissolved in methanol (20 mL). The mixture was stirred at room temperature for 45 mins to give a clear solution. The solution was allowed to stand in the air for 3 days. Yellow block-shaped single crystals of the title compound suitable for X-ray diffraction analysis were obtained at the bottom of the vessel.