3-(2-Formyl-phen-oxy)propanoic acid.

In the structure of the title compound, C(10)H(10)O(4), 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-H⋯O and O-H⋯O 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 = 194.18

Orthorhombic,

a = 15.269 (4) Å

b = 7.167 (2) Å

c = 17.136 (5) Å

V = 1875.2 (9) Å3

Z = 8

Mo Kα radiation

μ = 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 > 2σ(I)

3 standard reflections every 60 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.119

S = 1.02

1718 reflections

167 parameters

All H-atom parameters refined

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038079/zl2308sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038079/zl2308Isup2.hkl

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

C10H10O4	Dx = 1.376 Mg m−3
Mr = 194.18	Melting point: 381 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 15.269 (4) Å	θ = 6.2–19.0°
b = 7.167 (2) Å	µ = 0.11 mm−1
c = 17.136 (5) Å	T = 293 K
V = 1875.2 (9) Å3	Block, colourless
Z = 8	0.42 × 0.21 × 0.15 mm
F(000) = 816

Enraf–Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 25.3°, θmin = 2.4°
graphite	h = −18→0
ω/2θ scans	k = −8→0
1718 measured reflections	l = 0→20
1718 independent reflections	3 standard reflections every 60 min
964 reflections with I > 2σ(I)	intensity decay: 1%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	All H-atom parameters refined
S = 1.02	w = 1/[σ2(Fo2) + (0.0516P)2] where P = (Fo2 + 2Fc2)/3
1718 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
H21a	0.0220 (14)	0.495 (4)	0.3039 (14)	0.049 (7)*
H22b	−0.1019 (16)	0.478 (4)	0.2296 (16)	0.063 (9)*
H22a	−0.1276 (16)	0.540 (4)	0.3140 (14)	0.058 (9)*
H21b	0.0046 (17)	0.281 (4)	0.2824 (15)	0.058 (8)*
H5	0.2323 (19)	0.109 (4)	0.5447 (16)	0.073 (10)*
H3	0.1355 (15)	0.315 (4)	0.3435 (14)	0.049 (8)*
H41	−0.1930 (19)	0.040 (6)	0.2804 (19)	0.104 (13)*
H4	0.2503 (19)	0.196 (4)	0.4169 (15)	0.058 (9)*
H6	0.092 (2)	0.133 (4)	0.6011 (18)	0.081 (11)*
H1	−0.100 (2)	0.276 (4)	0.5065 (19)	0.099 (12)*
O3	−0.14623 (11)	0.1255 (3)	0.28392 (12)	0.0509 (6)
O2	−0.02664 (10)	0.3422 (3)	0.39246 (10)	0.0464 (5)
O4	−0.25446 (11)	0.3279 (2)	0.28021 (11)	0.0562 (6)
C23	−0.17679 (16)	0.2958 (3)	0.28326 (14)	0.0384 (6)
C2	0.04663 (17)	0.2827 (3)	0.43064 (16)	0.0414 (7)
C1	0.03508 (17)	0.2307 (4)	0.50805 (16)	0.0443 (7)
C21	−0.01910 (17)	0.3884 (4)	0.31172 (16)	0.0426 (7)
O1	−0.06445 (15)	0.2082 (3)	0.61361 (12)	0.0779 (7)
C22	−0.10849 (17)	0.4449 (4)	0.28378 (19)	0.0421 (7)
C3	0.12868 (17)	0.2735 (4)	0.39650 (18)	0.0511 (8)
C6	0.1071 (2)	0.1672 (5)	0.5502 (2)	0.0625 (9)
C11	−0.0514 (2)	0.2416 (4)	0.54553 (18)	0.0565 (8)
C4	0.1983 (2)	0.2109 (5)	0.4398 (2)	0.0690 (10)
C5	0.1876 (2)	0.1563 (6)	0.5161 (2)	0.0761 (11)

	U11	U22	U33	U12	U13	U23
O3	0.0400 (10)	0.0306 (11)	0.0823 (15)	0.0022 (8)	0.0009 (11)	0.0024 (10)
O2	0.0428 (10)	0.0563 (12)	0.0401 (11)	0.0032 (9)	0.0023 (9)	0.0062 (10)
O4	0.0409 (10)	0.0359 (10)	0.0919 (15)	0.0035 (9)	−0.0046 (11)	−0.0016 (11)
C23	0.0428 (15)	0.0324 (14)	0.0401 (15)	0.0047 (12)	0.0018 (13)	0.0013 (12)
C2	0.0481 (16)	0.0314 (14)	0.0449 (17)	−0.0040 (12)	−0.0047 (13)	−0.0030 (12)
C1	0.0533 (18)	0.0353 (15)	0.0442 (17)	−0.0071 (13)	−0.0018 (13)	−0.0035 (13)
C21	0.0438 (16)	0.0416 (17)	0.0424 (16)	−0.0065 (14)	0.0018 (13)	0.0020 (14)
O1	0.1120 (18)	0.0752 (16)	0.0466 (14)	−0.0116 (14)	0.0176 (12)	0.0007 (12)
C22	0.0500 (16)	0.0312 (16)	0.0451 (18)	−0.0034 (12)	−0.0004 (15)	0.0009 (14)
C3	0.0437 (16)	0.0558 (18)	0.0537 (19)	−0.0044 (14)	−0.0007 (16)	0.0009 (16)
C6	0.075 (2)	0.059 (2)	0.054 (2)	−0.0036 (18)	−0.011 (2)	−0.0018 (17)
C11	0.077 (2)	0.0448 (19)	0.047 (2)	−0.0066 (17)	0.0067 (18)	−0.0035 (15)
C4	0.0453 (19)	0.084 (3)	0.077 (3)	0.0022 (18)	−0.0088 (19)	−0.009 (2)
C5	0.072 (3)	0.080 (3)	0.077 (3)	0.009 (2)	−0.031 (2)	0.000 (2)

O3—C23	1.306 (3)	C21—H21b	0.99 (3)
O3—H41	0.95 (4)	O1—C11	1.208 (3)
O2—C2	1.364 (3)	C22—H22b	0.96 (3)
O2—C21	1.427 (3)	C22—H22a	0.90 (3)
O4—C23	1.209 (3)	C3—C4	1.371 (4)
C23—C22	1.493 (3)	C3—H3	0.96 (2)
C2—C3	1.384 (4)	C6—C5	1.363 (5)
C2—C1	1.389 (4)	C6—H6	0.93 (3)
C1—C6	1.392 (4)	C11—H1	1.03 (3)
C1—C11	1.471 (4)	C4—C5	1.375 (5)
C21—C22	1.502 (4)	C4—H4	0.89 (3)
C21—H21a	1.00 (3)	C5—H5	0.91 (3)
C23—O3—H41	110 (2)	C21—C22—H22b	106.2 (15)
C2—O2—C21	118.1 (2)	C23—C22—H22a	108.5 (17)
O4—C23—O3	121.9 (2)	C21—C22—H22a	108.3 (17)
O4—C23—C22	123.3 (2)	H22b—C22—H22a	113 (2)
O3—C23—C22	114.8 (2)	C4—C3—C2	119.2 (3)
O2—C2—C3	123.7 (3)	C4—C3—H3	121.8 (14)
O2—C2—C1	116.0 (2)	C2—C3—H3	118.9 (15)
C3—C2—C1	120.4 (3)	C5—C6—C1	120.6 (4)
C6—C1—C2	118.9 (3)	C5—C6—H6	127 (2)
C6—C1—C11	120.0 (3)	C1—C6—H6	112.3 (19)
C2—C1—C11	121.1 (3)	O1—C11—C1	124.0 (3)
O2—C21—C22	107.3 (2)	O1—C11—H1	123.9 (19)
O2—C21—H21a	111.0 (14)	C1—C11—H1	112.0 (19)
C22—C21—H21a	108.9 (14)	C3—C4—C5	121.0 (3)
O2—C21—H21b	110.0 (16)	C3—C4—H4	119.5 (18)
C22—C21—H21b	112.4 (15)	C5—C4—H4	119.2 (18)
H21a—C21—H21b	107 (2)	C6—C5—C4	119.9 (4)
C23—C22—C21	116.3 (2)	C6—C5—H5	118.0 (19)
C23—C22—H22b	104.2 (16)	C4—C5—H5	122.1 (19)
C21—O2—C2—C3	3.4 (4)	O2—C2—C3—C4	−179.7 (3)
C21—O2—C2—C1	−176.9 (2)	C1—C2—C3—C4	0.6 (4)
O2—C2—C1—C6	179.5 (2)	C2—C1—C6—C5	0.0 (4)
C3—C2—C1—C6	−0.8 (4)	C11—C1—C6—C5	179.9 (3)
O2—C2—C1—C11	−0.4 (4)	C6—C1—C11—O1	4.3 (4)
C3—C2—C1—C11	179.3 (3)	C2—C1—C11—O1	−175.8 (3)
C2—O2—C21—C22	178.8 (2)	C2—C3—C4—C5	0.4 (5)
O4—C23—C22—C21	162.1 (3)	C1—C6—C5—C4	1.0 (5)
O3—C23—C22—C21	−20.0 (4)	C3—C4—C5—C6	−1.2 (6)
O2—C21—C22—C23	−65.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.94 (3)	2.46 (3)	2.851 (4)	105 (2)
C11—H1···O2	1.03 (3)	2.30 (3)	2.746 (4)	105 (2)
O3—H41···O4i	0.94 (4)	1.72 (4)	2.618 (3)	158 (3)
C21—H21a···O1ii	1.00 (3)	2.64 (3)	3.409 (4)	134.5 (2)
C22—H22b···O1iii	0.96 (3)	2.46 (3)	3.187 (4)	132 (2)
C21—H21a···O3iv	1.00 (3)	2.60 (2)	3.456 (3)	144 (2)
C3—H3···O4v	0.96 (2)	2.71 (2)	3.536 (4)	144.9 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H41⋯O4i	0.94 (4)	1.72 (4)	2.618 (3)	158 (3)
C21—H21a⋯O1ii	1.00 (3)	2.64 (3)	3.409 (4)	134.5 (2)
C22—H22b⋯O1iii	0.96 (3)	2.46 (3)	3.187 (4)	132 (2)
C21—H21a⋯O3iv	1.00 (3)	2.60 (2)	3.456 (3)	144 (2)
C3—H3⋯O4v	0.96 (2)	2.71 (2)	3.536 (4)	144.9 (2)

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