3-(2-Formyl­phen­oxy)propanoic acid

Collas, A.; Vande Velde, C.M.L.; Blockhuys, F.

doi:10.1107/S1600536810038079

Volume 66
Part 10
Page o2662
October 2010

Received 13 September 2010
Accepted 23 September 2010
Online 30 September 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.119
Data-to-parameter ratio = 10.3
Details

3-(2-Formylphenoxy)propanoic acid

Alain Collas,^a Christophe M. L. Vande Velde ^a ⁺ and Frank Blockhuys ^a ^*

^aDepartment of Chemistry, University of Antwerp, Universiteitsplein 1, B-2610 Wilrijk, Belgium
Correspondence e-mail: frank.blockhuys@ua.ac.be

In the structure of the title compound, C₁₀H₁₀O₄, the carboxyl group forms a catemer motif in the [100] direction instead of the expected dimeric structures. The carboxylic acid group is found in the syn conformation and the three-dimensional organization in the crystal is based on C-HO and O-HO interactions.

Related literature

For the synthesis, see: Zawadowska (1963); Jarvest et al. (2005). For related structures, see: Gresham et al. (1949); Leiserowitz (1976); Borthwick (1980); Kennard et al. (1982); Shockravi et al. (2004); Gao & Ng (2006). For applications of poly(p-phenylene vinylene) oligomers (PPVs), see: Chemla (1987); Bandyopadhyay & Pal (2003). For hydrogen bonding and crystal engineering, see: Desiraju (1997); Steiner (2002).

Experimental

Crystal data

C₁₀H₁₀O₄
M_r = 194.18
Orthorhombic, P b c a
a = 15.269 (4) Å
b = 7.167 (2) Å
c = 17.136 (5) Å
V = 1875.2 (9) Å³
Z = 8
Mo K radiation
= 0.11 mm^-1
T = 293 K
0.42 × 0.21 × 0.15 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
1718 measured reflections
1718 independent reflections
964 reflections with I > 2(I)
3 standard reflections every 60 min intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.119
S = 1.02
1718 reflections
167 parameters
All H-atom parameters refined
_max = 0.17 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H41O4ⁱ	0.94 (4)	1.72 (4)	2.618 (3)	158 (3)
C21-H21aO1ⁱⁱ	1.00 (3)	2.64 (3)	3.409 (4)	134.5 (2)
C22-H22bO1ⁱⁱⁱ	0.96 (3)	2.46 (3)	3.187 (4)	132 (2)
C21-H21aO3^iv	1.00 (3)	2.60 (2)	3.456 (3)	144 (2)
C3-H3O4^v	0.96 (2)	2.71 (2)	3.536 (4)	144.9 (2)
Symmetry codes: (i) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) -x, -y+1, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2308 ).

Acknowledgements

CVV thanks the Fund for Scientific Research (FWO Vlaanderen) for a grant as a research assistant. AC wishes to thank the Institute for the Promotion of Innovation by Science and Technology in Flanders (IWT) for a predoctoral grant.

References

Bandyopadhyay, A. & Pal, A. J. (2003). Appl. Phys. Lett. 82, 1215-1217.
Borthwick, P. W. (1980). Acta Cryst. B36, 628-632.
Chemla, D. S. (1987). Nonlinear Optical Properties of Organic Molecules and Crystals. Boston: Academic Press.
Desiraju, G. R. (1997). Chem. Commun. 16, 1475-1482.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gao, S. & Ng, S. W. (2006). Acta Cryst. E62, o3420-o3421.
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Shockravi, A., Alizadeh, R., Aghabozorg, H., Mohebbi, L., Moradi, K. S. & Moghimi, A. (2004). Iran. J. Chem. Chem. Eng. 23, 37-44.
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Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.
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organic compounds