Crystal structure of 3-(4-(carboxymethoxy)phenyl)propanoic acid, C11H12O5

C11H12O5, triclinic, P1 (no. 1), a = 5.272(1) Å, b = 7.294(2) Å, c = 7.595(2)Å, = 79.286(3)°, = 70.251(3)°, = 71.238(3)°, V = 259.3 Å, Z = 1, Rgt(F) = 0.040, wRref(F) = 0.103, T = 291 K. Source of material To amixture of 8.3 g 3-(4-hydroxyphenyl)propanoic acid and 6 g chloroacetic acid at RT was added a little polyglycol (polyoxyethylene glycol) under stirring.After the reactionmixture became clear, the temperature was quickly elevated to 363 K and maintained for 4 h with vigorous stirring under reflux. The resulting mixture was cooled to room temperature and was acidified with HCl to pH2-3.A gray product precipitated,whichwas filtered off and washed with 2 × 10 ml ice water, 10.1 g (yield 88.3 %) of the target product remained after drying in vacuo. Crystals appropriate for X-ray data collection were obtained by recrystallizing from deionized water (m.p. 485-486 K). Elemental analysis  found: C, 58.56 %; H, 5.53 %; calc. for C11H12O5: C, 58.88 %; H, 5.35 %. H NMR and C NMR data are available in the CIF. Discussion In recent years, the self-assembly of supramolecular architectures by exploiting non-covalent forces has been a central theme in the design of new solid materials with intriguing structures such as brick wall [1], square grid [2], honeycomb [3] and other shapes [4,5]. Hydrogen bonding is one of the non-covalent forces to construct supermolecular architectures. The carboxylic acid moiety can act as either hydrogen bond donor or hydrogen bond acceptor, and represents perhaps the most widely observed and exploited supramolecular synthons. Terephthalic acid as a representative of rigid dicarboxylic acids has been widely used to assemble supramolecular structures. Similar studies on polycarboxylate ligands with characteristics of both flexibility and rigidity have rarely been reported. Phenoxyacetic acid is an aromatic carboxylic acid with rigidity and flexibility, and has potential application on plant growth adjustment and herbicide. In the title crystal structure, the bond lengths of COether are 1.440(4) Å and 1.411(5) Å, these values are similar to those reported in [Zn(oda)(H2O)2 · H2O]n (oda = oxydiacetate) [6]; and the bond lengths of COcarboxylate in propanate and oxyacetate are 1.319(5) Å, 1.201(5) Å and 1.291(5) Å, 1.240(6) Å, respectively, these values are similar to those reported in ()-2-(1,2,3, 4,4a,5,6,7,8,8aa-decahydro-4ab,8a-dimethyl-7-oxo-2b-naphthyl)propionic acid [7] and benzene-1,4-dicarboxylic acid N,N-dimethylformamide disolvate [8], respectively. In the title structure oxyacetate, propanate and phenyl ring are roughly planar, with a mean deviation of 0.0414 Å. There are two OH···O hydrogen bonds between each adjacent 3-(4-(carboxymethoxy)phenyl)propanoic acid molecules with O···O distances 2.639(4) Å  2.645(4) Å, which link the molecules in head-to-tail mode to an infinite planar chain along [010]. Intermolecular CH···O interactions further join the chains into layers parallel to (010). Z. Kristallogr. NCS 222 (2007) 137-138 / DOI 10.1524/ncrs.2007. 0055 137 © by Oldenbourg Wissenschaftsverlag, München Crystal: colorless block, size 0.11 × 0.17 × 0.33 mm Wavelength: Mo K radiation (0.71073 Å) : 1.14 cm−1 Diffractometer, scan mode: Bruker SMART CCD, / 2 max: 51° N(hkl)measured, N(hkl)unique: 1989, 1715 Criterion for Iobs, N(hkl)gt: Iobs > 2 (Iobs), 1352 N(param)refined: 147 Programs: SHELXS-97 [9], SHELXL-97 [10], SHELXTL [11] Table 1. Data collection and handling.