Methyl 2-[2-(2,6-dichloro­anilino)­phenyl]­acetate

Rashid Saleem; Ghulam Shabir; Muhammad Hanif; Ghulam Qadeer; Wai-Yeung Wong

doi:10.1107/S1600536808038336

. 2008 Nov 20;64(Pt 12):o2400. doi: 10.1107/S1600536808038336

Methyl 2-[2-(2,6-dichloroanilino)phenyl]acetate

Rashid Saleem ^a, Ghulam Shabir ^b, Muhammad Hanif ^b, Ghulam Qadeer ^b,^*, Wai-Yeung Wong ^c

PMCID: PMC2959891 PMID: 21581370

Abstract

In the title compound, C₁₅H₁₃Cl₂NO₂, the dihedral angle between the aromatic rings is 63.80 (12)°. The conformation may be stabilized by a weak N—H⋯O hydrogen bond. In the crystal structure, a short C—Cl⋯π interaction occurs, with a Cl⋯π separation of 3.5706 (13) Å.

Related literature

For general background, see: Hashem et al. (2007 ▶); Husain et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₃Cl₂NO₂
M _r = 310.16
Monoclinic,
a = 4.9319 (4) Å
b = 20.0288 (14) Å
c = 14.5542 (10) Å
β = 97.711 (1)°
V = 1424.66 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 173 (2) K
0.38 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.850, T _max = 1.000 (expected range = 0.776–0.913)
8526 measured reflections
3423 independent reflections
2777 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.171
S = 1.04
3423 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); 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 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038336/pv2122sup1.cif

e-64-o2400-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038336/pv2122Isup2.hkl

e-64-o2400-Isup2.hkl^{(167.9KB, 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—H1A⋯O1	0.88	2.64	3.152 (2)	118

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Acknowledgments

The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan.

supplementary crystallographic information

Comment

Esters are important intermediates in heterocyclic chemistry and have been used for the synthesis of various biologically active five-membered heterocyles such as butenolides, pyrrolones (Husain et al., 2005), oxadiazoles and triazoles (Hashem et al., 2007). In view of the versatility of these compounds, we have synthesized the title compound and report herein its crystal structure.

In the title compound (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The planar ester group (O1/O2/C13/C14/C15) is oriented with respect to the plane of the benzene ring (C7–C12) at an angle 41.33 (2)°. There is a short intramolecular N—H···O hydrogen bond (Table 1) and a π-ring interaction of the type C—Cl···Cg with Cl1···Cg1 (centroid of C1–C6 ring) perpendicular distance 3.5706 (13) Å.

Experimental

A mixture of 2-(2,6-dichlorophenylamino)benzoic acid (2.81 g, 10 mmol) and absolute methanol (50 ml) in the presence of a few drops of sulfuric acid was refluxed for 5 h. The excess of the solvent was removed by distillation. The solid residue was filltered off, washed with water and recystallized from ethanol (30%) to give the title compound. Suitable single crystals of the title compound were obtained by slow evaporation of an ethanol solution at room temperature. (Yield, 88%; m.p. 331–332 K)