2-(4-Fluoro­phen­yl)-2-oxoethyl 4-meth­oxy­benzoate

Hoong-Kun Fun; Wan-Sin Loh; B Garudachari; Arun M Isloor; M N Satyanarayan

doi:10.1107/S1600536811049233

. 2011 Nov 30;67(Pt 12):o3456. doi: 10.1107/S1600536811049233

2-(4-Fluorophenyl)-2-oxoethyl 4-methoxybenzoate

Hoong-Kun Fun ^a,^*,^‡, Wan-Sin Loh ^a,^§, B Garudachari ^b, Arun M Isloor ^b, M N Satyanarayan ^c

PMCID: PMC3239086 PMID: 22199934

Abstract

In the title compound, C₁₆H₁₃FO₄, the dihedral angle between the benzene rings is 84.28 (8)°. In the crystal, C—H⋯F and C—H⋯O hydrogen bonds link the molecules to form a three-dimensional network. The crystal structure is consolidated by C—H⋯π interactions and short F⋯F contacts [2.7748 (14) Å] also occur.

Related literature

For related structures and background to phenacyl benzoates, see: Fun et al. (2011a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₆H₁₃FO₄
M _r = 288.26
Monoclinic,
a = 9.3523 (2) Å
b = 10.1949 (2) Å
c = 15.6465 (4) Å
β = 118.842 (2)°
V = 1306.77 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.29 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.967, T _max = 0.984
18005 measured reflections
4669 independent reflections
3194 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.151
S = 1.03
4669 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049233/hb6504sup1.cif

e-67-o3456-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049233/hb6504Isup2.hkl

e-67-o3456-Isup2.hkl^{(228.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811049233/hb6504Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯F1ⁱ	0.95	2.55	3.1334 (17)	120
C8—H8B⋯O3ⁱⁱ	0.99	2.43	3.3517 (19)	154
C11—H11A⋯O4ⁱⁱⁱ	0.95	2.53	3.380 (2)	150
C1—H1A⋯Cg2^iv	0.95	2.59	3.3693 (17)	139
C8—H8A⋯Cg1^v	0.99	2.83	3.5309 (19)	128

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

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young scientist award. SMN thanks the Department of Information Technology, New Delhi, India, for financial support.

supplementary crystallographic information

Comment

As part of our ongoing studies of phenacyl benzoates (Fun et al., 2011a,b), we now report the synthesis and structure of the title compound.

In the title compound (Fig. 1), the dihedral angle formed between the fluoro-substituted (C1–C6) and the methoxy-substituted (C10–C15) benzene rings is 84.28 (8)°. Bond lengths and angles are within the normal ranges and are comparable to the related structures (Fun et al., 2011a,b).

In the crystal (Fig. 2), C4—H4A···F1, C8—H8B···O3 and C11—H11A···O4 hydrogen bonds (Table 1) link the molecules together to form a three-dimensional network. The crystal structure is further stabilized by C–H···π interactions (Table 1) involving the fluoro-substituted (Cg1) and the methoxy-substituted (Cg2) benzene rings.

Experimental

A mixture of 4-methoxybenzoic acid (1.0 g, 0.0065 mol), potassium carbonate (0.99 g, 0.0072 mol) and 2-bromo-1-(4-fluorophenyl)ethanone (1.41 g, 0.0065 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colourless needle-shaped crystals of 2-(4-fluorophenyl)-2-oxoethyl 4-methoxybenzoate began to separate. It was collected by filtration and recrystallized from ethanol to yield yellow blocks of (I). Yield: 1.72 g, 91.0%. M.p: 387–388 K.