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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 [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.093
Data-to-parameter ratio = 13.5
Details
Open access

2-(Acetoxymethyl)benzoic acid

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)-H...O(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[Gorter-Laroij, G. M. & Kooyman, E. C. (1972). J. Catal. 25, 230-237.]). For related structures, see Kan et al. (2012[Kan, W.-Q., Ma, J.-F., Liu, Y.-L. & Yang, J. (2012). CrystEngComm, 14, 2316-2326.]); Liu et al. (2002[Liu, R., Valiyaveettil, S., Mok, K.-F., Vittal, J. J. & Hoong, A. K. M. (2002). CrystEngComm, 4, 574-579.]); Valentine et al. (1992[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.]). For hydrogen-bonding motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For a description of the Cambridge Structural Database (CSD), see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C10H10O4

  • Mr = 194.18

  • Triclinic, [P \overline 1]

  • a = 6.2134 (9) Å

  • b = 8.2415 (9) Å

  • c = 9.6280 (11) Å

  • [alpha] = 77.54 (1)°

  • [beta] = 83.364 (11)°

  • [gamma] = 73.081 (12)°

  • V = 459.84 (10) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.848, Tmax = 1.000

  • 2819 measured reflections

  • 1767 independent reflections

  • 1678 reflections with I > 2[sigma](I)

  • Rint = 0.012

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-H...A D-H H...A D...A D-H...A
O2-H2...O1i 0.971 (16) 1.667 (15) 2.6316 (12) 171.6 (12)
C4-H4...O4ii 0.95 2.43 3.3685 (15) 168
C8-H8A...O2iii 0.99 2.67 3.5747 (14) 152
C10-H10B...Cg1iii 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP in WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [ISI] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gorter-Laroij, G. M. & Kooyman, E. C. (1972). J. Catal. 25, 230-237.  [CrossRef] [ChemPort] [ISI]
Kan, W.-Q., Ma, J.-F., Liu, Y.-L. & Yang, J. (2012). CrystEngComm, 14, 2316-2326.  [ISI] [CSD] [CrossRef] [ChemPort]
Liu, R., Valiyaveettil, S., Mok, K.-F., Vittal, J. J. & Hoong, A. K. M. (2002). CrystEngComm, 4, 574-579.  [ISI] [CSD] [CrossRef] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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.  [CrossRef]


Acta Cryst (2013). E69, o259  [ doi:10.1107/S1600536813000780 ]

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