Methyl 3-(4-methoxy­benzo­yl)propionate

Sajid Ali; Ghulam Qadeer; Nasim Hasan Rama; Wai-Yeung Wong

doi:10.1107/S1600536808037720

. 2008 Nov 20;64(Pt 12):o2391. doi: 10.1107/S1600536808037720

Methyl 3-(4-methoxybenzoyl)propionate

Sajid Ali ^a, Ghulam Qadeer ^a, Nasim Hasan Rama ^a,^*, Wai-Yeung Wong ^b

PMCID: PMC2960146 PMID: 21581361

Abstract

The asymmetric unit of the title compound, C₁₂H₁₄O₃, contains two independent molecules, in which the benzene rings are oriented at a dihedral angle of 72.08 (3)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. There are also C—H⋯π contacts between aromatic CH groups and the benzene rings.

Related literature

For general background, see: Hashem et al. (2007 ▶); Husain et al.(2005 ▶). For a related structure, see: Ali et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₂H₁₄O₃
M _r = 206.23
Monoclinic,
a = 34.762 (4) Å
b = 5.2861 (7) Å
c = 27.752 (3) Å
β = 117.182 (2)°
V = 4536.5 (9) Å³
Z = 16
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.28 × 0.26 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.798, T _max = 0.980
13099 measured reflections
5456 independent reflections
3364 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.174
S = 1.01
5456 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037720/hk2571sup1.cif

e-64-o2391-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037720/hk2571Isup2.hkl

e-64-o2391-Isup2.hkl^{(267.2KB, 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
C24—H24A⋯O1ⁱ	0.96	2.53	3.467 (3)	164
C4—H4A⋯Cg1ⁱⁱ	0.93	3.17	3.858 (4)	133
C6—H6A⋯Cg2ⁱⁱⁱ	0.93	3.26	4.051 (3)	144
C18—H18A⋯Cg1	0.93	3.20	3.940 (3)	138

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C2–C7 and C14–C19 rings.

Acknowledgments

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

supplementary crystallographic information

Comment

Benzoyl propionic acids and 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 synthesized the title compound and reported herein its crystal structure.

The asymmetric unit of the title compound contains two crystallographically independent molecules of similar geometry (Fig.1). The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable with the corresponding values in 3-(4-methoxybenzoyl)propionic acid (Ali et al., 2008). Rings A (C2-C7) and B (C14-C19) are, of course, planar and they are oriented at a dihedral angle of 72.08 (3)°.

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure. There also exist C—H···π contacts (Table 1) between the aromatic CH groups and the benzene rings.

Experimental

For the preparation of the title compound, the mixture of 3-(4-methoxybenzoyl) propionic acid (2.08 g, 10 mmol) and absolute methanol (50 ml) in the presence of a few drops of suphuric acid was refluxed for 5 h. The excess of solvent was removed by distillation. The solid residue for filltered off, washed with water and recystallized from ethanol (30%) to give the title compound. Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (yield; 83%, m.p. 308-309 K).