(Z)-2-Hydr-oxy-3-(4-methoxy-phen-yl)acrylic acid.

In the structure of the title compound, C(10)H(10)O(4), inversion dimers linked by pairs of O-H⋯O hydrogen bonds link the carboxylic acid groups. Further O-H⋯O links cross-link the dimers into sheets running along the b-axis direction.

Related literature

For 3-phenyl­acrylic acid as inter­mediates for compounds with biological activity, see: Chen et al. (1993 ▶); Igarashi et al. (1997 ▶); Xiao et al. (2007 ▶); Yu et al. (1991 ▶). The title compound was synthesized during the course of our work on the synthesis of potential anti­cancer compounds, see: Xiao et al. (2008a ▶,b ▶).

Experimental

Crystal data

C10H10O4

M = 194.18

Monoclinic,

a = 6.7440 (13) Å

b = 5.4290 (11) Å

c = 24.933 (5) Å

β = 93.28 (3)°

V = 911.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.20 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.995

1783 measured reflections

1634 independent reflections

1062 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.229

S = 1.07

1634 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050077/jh2116sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050077/jh2116Isup2.hkl

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

C10H10O4	F(000) = 408
Mr = 194.18	Dx = 1.415 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 6.7440 (13) Å	θ = 10–13°
b = 5.4290 (11) Å	µ = 0.11 mm−1
c = 24.933 (5) Å	T = 298 K
β = 93.28 (3)°	Block, colorless
V = 911.4 (3) Å3	0.20 × 0.10 × 0.05 mm
Z = 4

Bruker SMART APEX CCD diffractometer	1634 independent reflections
Radiation source: fine-focus sealed tube	1062 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scan	θmax = 25.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.978, Tmax = 0.995	k = 0→6
1783 measured reflections	l = 0→29

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.229	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1176P)2 + 0.6125P] where P = (Fo2 + 2Fc2)/3
1634 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.25 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
O1	−0.2792 (4)	0.2913 (6)	0.29127 (12)	0.0686 (10)
C1	−0.3926 (7)	0.0765 (10)	0.2992 (2)	0.0735 (14)
H1A	−0.5117	0.0816	0.2762	0.110*
H1B	−0.4268	0.0681	0.3360	0.110*
H1C	−0.3163	−0.0662	0.2907	0.110*
O2	0.5210 (4)	0.0927 (5)	0.44683 (13)	0.0627 (9)
H2A	0.6147	0.0066	0.4352	0.075*
C2	−0.1051 (6)	0.3189 (8)	0.32160 (16)	0.0511 (10)
O3	0.7993 (4)	0.6459 (5)	0.45988 (12)	0.0625 (9)
H3B	0.9134	0.6691	0.4754	0.094*
C3	0.0063 (6)	0.5256 (9)	0.30978 (18)	0.0641 (13)
H3A	−0.0385	0.6312	0.2823	0.077*
O4	0.8501 (4)	0.2652 (5)	0.49281 (11)	0.0554 (8)
C4	0.1819 (7)	0.5746 (9)	0.33834 (18)	0.0622 (12)
H4A	0.2529	0.7155	0.3304	0.075*
C5	0.2557 (5)	0.4185 (7)	0.37875 (15)	0.0461 (9)
C6	0.1417 (6)	0.2101 (8)	0.38927 (16)	0.0517 (10)
H6A	0.1882	0.1006	0.4158	0.062*
C7	−0.0345 (6)	0.1624 (8)	0.36199 (17)	0.0552 (11)
H7A	−0.1077	0.0241	0.3705	0.066*
C8	0.4431 (6)	0.4777 (7)	0.40817 (15)	0.0484 (10)
H8A	0.4839	0.6407	0.4056	0.058*
C9	0.5639 (5)	0.3336 (7)	0.43806 (16)	0.0479 (9)
C10	0.7504 (5)	0.4146 (8)	0.46618 (16)	0.0483 (10)

	U11	U22	U33	U12	U13	U23
O1	0.0498 (16)	0.078 (2)	0.074 (2)	−0.0062 (16)	−0.0308 (15)	0.0012 (17)
C1	0.057 (2)	0.077 (3)	0.084 (3)	−0.006 (3)	−0.019 (2)	−0.015 (3)
O2	0.0473 (15)	0.0473 (17)	0.090 (2)	−0.0052 (13)	−0.0239 (15)	0.0071 (16)
C2	0.0456 (19)	0.051 (2)	0.055 (2)	0.0079 (19)	−0.0146 (18)	−0.0052 (19)
O3	0.0499 (16)	0.0494 (17)	0.085 (2)	−0.0063 (14)	−0.0251 (15)	0.0020 (15)
C3	0.053 (2)	0.070 (3)	0.065 (3)	0.008 (2)	−0.027 (2)	0.008 (2)
O4	0.0408 (14)	0.0575 (18)	0.0655 (17)	−0.0033 (14)	−0.0187 (13)	0.0021 (15)
C4	0.056 (2)	0.054 (3)	0.075 (3)	−0.002 (2)	−0.013 (2)	0.008 (2)
C5	0.0430 (19)	0.0406 (19)	0.052 (2)	0.0067 (18)	−0.0200 (17)	−0.0055 (18)
C6	0.049 (2)	0.052 (2)	0.051 (2)	0.0037 (19)	−0.0200 (17)	0.0046 (19)
C7	0.045 (2)	0.052 (2)	0.066 (3)	−0.004 (2)	−0.0200 (19)	−0.002 (2)
C8	0.044 (2)	0.044 (2)	0.055 (2)	−0.0037 (18)	−0.0130 (18)	−0.0002 (18)
C9	0.0402 (19)	0.046 (2)	0.056 (2)	−0.0004 (18)	−0.0125 (17)	−0.0007 (18)
C10	0.0343 (17)	0.049 (2)	0.060 (2)	0.0007 (18)	−0.0080 (17)	0.000 (2)

O1—C2	1.368 (5)	C3—H3A	0.9300
O1—C1	1.415 (6)	O4—C10	1.225 (4)
C1—H1A	0.9600	C4—C5	1.387 (6)
C1—H1B	0.9600	C4—H4A	0.9300
C1—H1C	0.9600	C5—C6	1.401 (6)
O2—C9	1.360 (5)	C5—C8	1.460 (5)
O2—H2A	0.8500	C6—C7	1.360 (5)
C2—C7	1.381 (6)	C6—H6A	0.9300
C2—C3	1.391 (6)	C7—H7A	0.9300
O3—C10	1.310 (5)	C8—C9	1.327 (5)
O3—H3B	0.8499	C8—H8A	0.9300
C3—C4	1.372 (6)	C9—C10	1.472 (5)
C2—O1—C1	117.8 (3)	C4—C5—C6	116.9 (3)
O1—C1—H1A	109.5	C4—C5—C8	119.7 (4)
O1—C1—H1B	109.5	C6—C5—C8	123.5 (3)
H1A—C1—H1B	109.5	C7—C6—C5	122.2 (4)
O1—C1—H1C	109.5	C7—C6—H6A	118.9
H1A—C1—H1C	109.5	C5—C6—H6A	118.9
H1B—C1—H1C	109.5	C6—C7—C2	120.2 (4)
C9—O2—H2A	107.7	C6—C7—H7A	119.9
O1—C2—C7	125.8 (4)	C2—C7—H7A	119.9
O1—C2—C3	115.4 (4)	C9—C8—C5	129.7 (4)
C7—C2—C3	118.8 (4)	C9—C8—H8A	115.2
C10—O3—H3B	108.4	C5—C8—H8A	115.2
C4—C3—C2	120.5 (4)	C8—C9—O2	121.9 (3)
C4—C3—H3A	119.8	C8—C9—C10	124.9 (4)
C2—C3—H3A	119.8	O2—C9—C10	113.2 (3)
C3—C4—C5	121.4 (4)	O4—C10—O3	124.4 (3)
C3—C4—H4A	119.3	O4—C10—C9	119.2 (4)
C5—C4—H4A	119.3	O3—C10—C9	116.3 (3)
C1—O1—C2—C7	−4.2 (6)	O1—C2—C7—C6	179.9 (4)
C1—O1—C2—C3	176.1 (4)	C3—C2—C7—C6	−0.4 (6)
O1—C2—C3—C4	178.8 (4)	C4—C5—C8—C9	−161.8 (4)
C7—C2—C3—C4	−0.9 (7)	C6—C5—C8—C9	18.8 (7)
C2—C3—C4—C5	1.4 (7)	C5—C8—C9—O2	−1.9 (7)
C3—C4—C5—C6	−0.5 (7)	C5—C8—C9—C10	−179.8 (4)
C3—C4—C5—C8	−180.0 (4)	C8—C9—C10—O4	179.8 (4)
C4—C5—C6—C7	−0.9 (6)	O2—C9—C10—O4	1.8 (5)
C8—C5—C6—C7	178.5 (4)	C8—C9—C10—O3	−1.2 (6)
C5—C6—C7—C2	1.4 (7)	O2—C9—C10—O3	−179.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2	0.93	2.33	2.931 (5)	122
C8—H8A···O3	0.93	2.46	2.813 (5)	103
O2—H2A···O3i	0.85	2.38	3.073 (4)	139
O3—H3B···O4ii	0.85	1.78	2.626 (4)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O4ii	0.85	1.78	2.626 (4)	177

Symmetry codes: (i) ; (ii) .