2-(Acet­oxy­meth­yl)benzoic acid

Gainsford, G.J.; Schwörer, R.

doi:10.1107/S1600536813000780

Volume 69
Part 2
Page o259
February 2013

Received 28 November 2012
Accepted 8 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R = 0.033
wR = 0.093
Data-to-parameter ratio = 13.5
Details

2-(Acetoxymethyl)benzoic acid

Graeme J. Gainsford ^a ^* and Ralf Schwörer ^a

^aCarbohydrate Chemistry Group, Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand
Correspondence e-mail: g.gainsford@irl.cri.nz

The title compound, C₁₀H₁₀O₄, crystallizes with the well-known carboxylic acid dimer-forming R₂²(8) hydrogen-bond motif. Chains approximately parallel to (-1-12) are then built through C(methylene,phenyl)-HO(carbonyl) interactions [C(6) and C(8) motifs] with one (methyl)C-H [pi] interaction providing interplanar binding. The weakness of the latter interaction is consistent with the difficulty experienced in obtaining suitable single crystals.

Related literature

For details of the synthesis, see: Gorter-Laroij & Kooyman (1972). For related structures, see Kan et al. (2012); Liu et al. (2002); Valentine et al. (1992). For hydrogen-bonding motifs, see: Bernstein et al. (1995). For a description of the Cambridge Structural Database (CSD), see: Allen (2002).

Experimental

Crystal data

C₁₀H₁₀O₄
M_r = 194.18
Triclinic, $[P \overline 1]$
a = 6.2134 (9) Å
b = 8.2415 (9) Å
c = 9.6280 (11) Å
= 77.54 (1)°
= 83.364 (11)°
= 73.081 (12)°
V = 459.84 (10) Å³
Z = 2
Cu K radiation
= 0.92 mm^-1
T = 120 K
0.58 × 0.28 × 0.18 mm

Data collection

Oxford Diffraction SuperNova diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.848, T_max = 1.000
2819 measured reflections
1767 independent reflections
1678 reflections with I > 2(I)
R_int = 0.012

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.093
S = 1.08
1767 reflections
131 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 phenyl ring.

D-HA	D-H	HA	DA	D-HA
O2-H2O1ⁱ	0.971 (16)	1.667 (15)	2.6316 (12)	171.6 (12)
C4-H4O4ⁱⁱ	0.95	2.43	3.3685 (15)	168
C8-H8AO2ⁱⁱⁱ	0.99	2.67	3.5747 (14)	152
C10-H10BCg1ⁱⁱⁱ	0.98	2.82	3.5703 (13)	134
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x+1, y-1, z; (iii) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP in WinGX (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2082 ).

Acknowledgements

We thank Dr J Wikaira of the University of Canterbury, New Zealand, for the data collection.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gorter-Laroij, G. M. & Kooyman, E. C. (1972). J. Catal. 25, 230-237.
Kan, W.-Q., Ma, J.-F., Liu, Y.-L. & Yang, J. (2012). CrystEngComm, 14, 2316-2326.
Liu, R., Valiyaveettil, S., Mok, K.-F., Vittal, J. J. & Hoong, A. K. M. (2002). CrystEngComm, 4, 574-579.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Valentine, J. J., Nakanishi, S., Hageman, D. L., Snider, R. M., Spencer, R. W. & Vinicj, F. J. (1992). Bioorg. Med. Chem. Lett. 2, 233-338.

organic compounds