3-(4-Methoxy-benzo-yl)propionic acid.

In the crystal of the title compound, C(11)H(12)O(4), inversion dimers arise from pairs of intermolecular O-H⋯O hydrogen bonds and C-H⋯O bonds further consolidate the packing. There is also a C-H⋯π contact between the benzene ring and the methyl-ene group.

Related literature

For general background, see: Hashem et al. (2007 ▶); Husain et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H12O4

M = 208.21

Monoclinic,

a = 5.0511 (3) Å

b = 10.0219 (7) Å

c = 20.0840 (12) Å

β = 90.107 (6)°

V = 1016.67 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 150 (1) K

0.20 × 0.18 × 0.13 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer

Absorption correction: integration (Coppens, 1970 ▶) T min = 0.979, T max = 0.987

8320 measured reflections

2236 independent reflections

1662 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.112

S = 1.13

2236 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: COLLECT and DENZO (Otwinowski & Minor, 1997 ▶); data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034508/hk2556sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034508/hk2556Isup2.hkl

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

C11H12O4	F(000) = 440
Mr = 208.21	Dx = 1.360 Mg m−3
Monoclinic, P21/c	Melting point: 419(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.0511 (3) Å	Cell parameters from 8408 reflections
b = 10.0219 (7) Å	θ = 1–27.5°
c = 20.0840 (12) Å	µ = 0.10 mm−1
β = 90.107 (6)°	T = 150 K
V = 1016.67 (11) Å3	Block, colorless
Z = 4	0.20 × 0.18 × 0.13 mm

Bruker–Nonius KappaCCD area-detector diffractometer	2236 independent reflections
Radiation source: fine-focus sealed tube	1662 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.0°
φ and ω scans	h = −6→6
Absorption correction: integration (Coppens, 1970)	k = −13→13
Tmin = 0.979, Tmax = 0.987	l = −26→22
8320 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0363P)2 + 0.36P] where P = (Fo2 + 2Fc2)/3
2236 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 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	0.0482 (3)	−0.08173 (13)	0.07156 (6)	0.0440 (4)
O2	−0.2693 (3)	0.06464 (14)	0.04647 (6)	0.0443 (4)
H2	−0.1915	0.0654	0.0107	0.053*
O3	0.1138 (2)	0.13027 (12)	0.19230 (6)	0.0398 (3)
O4	0.7706 (3)	−0.03563 (14)	0.44558 (7)	0.0477 (4)
C1	−0.1507 (3)	−0.01793 (17)	0.08665 (8)	0.0323 (4)
C2	−0.2850 (3)	−0.03301 (19)	0.15227 (8)	0.0355 (4)
H2A	−0.4267	−0.0977	0.1478	0.043*
H2B	−0.3645	0.0517	0.1644	0.043*
C3	−0.1025 (3)	−0.07690 (17)	0.20779 (8)	0.0317 (4)
H3A	−0.0091	−0.1569	0.1941	0.038*
H3B	−0.2075	−0.0989	0.2467	0.038*
C4	0.0958 (3)	0.02952 (16)	0.22605 (8)	0.0297 (4)
C5	0.2686 (3)	0.00865 (16)	0.28458 (8)	0.0287 (4)
C6	0.2583 (3)	−0.10711 (17)	0.32209 (8)	0.0333 (4)
H6	0.1367	−0.1730	0.3108	0.040*
C7	0.4243 (3)	−0.12673 (18)	0.37606 (9)	0.0363 (4)
H7	0.4169	−0.2059	0.4002	0.044*
C8	0.6011 (3)	−0.02784 (18)	0.39356 (8)	0.0343 (4)
C9	0.6134 (4)	0.09014 (18)	0.35680 (9)	0.0365 (4)
H9	0.7319	0.1570	0.3688	0.044*
C10	0.4502 (3)	0.10717 (17)	0.30291 (9)	0.0339 (4)
H10	0.4605	0.1855	0.2782	0.041*
C11	0.7813 (5)	−0.1587 (2)	0.48107 (11)	0.0561 (6)
H11A	0.6127	−0.1758	0.5013	0.067*
H11B	0.9151	−0.1535	0.5150	0.067*
H11C	0.8233	−0.2297	0.4508	0.067*

	U11	U22	U33	U12	U13	U23
O1	0.0500 (8)	0.0510 (8)	0.0311 (7)	0.0157 (7)	0.0057 (6)	−0.0004 (6)
O2	0.0502 (8)	0.0558 (8)	0.0268 (6)	0.0147 (7)	0.0026 (6)	0.0017 (6)
O3	0.0442 (7)	0.0337 (7)	0.0413 (7)	0.0016 (6)	−0.0026 (6)	0.0066 (6)
O4	0.0528 (8)	0.0466 (8)	0.0436 (8)	−0.0063 (7)	−0.0184 (6)	0.0049 (6)
C1	0.0358 (9)	0.0341 (9)	0.0268 (8)	−0.0008 (8)	−0.0027 (7)	−0.0039 (7)
C2	0.0317 (8)	0.0441 (10)	0.0307 (9)	−0.0015 (8)	0.0018 (7)	−0.0002 (8)
C3	0.0323 (8)	0.0360 (9)	0.0267 (8)	0.0005 (7)	0.0022 (7)	−0.0010 (7)
C4	0.0303 (8)	0.0295 (9)	0.0293 (8)	0.0062 (7)	0.0066 (7)	−0.0007 (7)
C5	0.0285 (8)	0.0288 (8)	0.0288 (8)	0.0017 (7)	0.0039 (6)	−0.0024 (7)
C6	0.0355 (9)	0.0306 (9)	0.0338 (9)	−0.0057 (7)	0.0001 (7)	−0.0005 (7)
C7	0.0408 (9)	0.0334 (9)	0.0348 (9)	−0.0025 (8)	−0.0015 (8)	0.0046 (7)
C8	0.0343 (9)	0.0381 (10)	0.0304 (9)	0.0015 (8)	−0.0025 (7)	−0.0023 (7)
C9	0.0372 (9)	0.0320 (9)	0.0402 (10)	−0.0068 (8)	−0.0040 (8)	−0.0032 (8)
C10	0.0364 (9)	0.0288 (9)	0.0364 (9)	0.0001 (7)	0.0031 (7)	0.0006 (7)
C11	0.0659 (14)	0.0541 (13)	0.0481 (12)	−0.0033 (11)	−0.0225 (10)	0.0106 (10)

O1—C1	1.230 (2)	C5—C6	1.384 (2)
O2—C1	1.301 (2)	C5—C10	1.396 (2)
O2—H2	0.8201	C6—C7	1.383 (2)
O3—C4	1.220 (2)	C6—H6	0.9300
O4—C8	1.352 (2)	C7—H7	0.9301
O4—C11	1.425 (2)	C8—C7	1.379 (2)
C1—C2	1.491 (2)	C8—C9	1.395 (2)
C2—C3	1.511 (2)	C9—H9	0.9300
C2—H2A	0.9700	C10—C9	1.370 (2)
C2—H2B	0.9699	C10—H10	0.9299
C3—H3A	0.9700	C11—H11A	0.9600
C3—H3B	0.9701	C11—H11B	0.9600
C4—C3	1.508 (2)	C11—H11C	0.9600
C5—C4	1.478 (2)
C1—O2—H2	109.2	C10—C5—C4	119.76 (15)
C8—O4—C11	117.38 (15)	C7—C6—C5	121.48 (16)
O1—C1—O2	123.60 (15)	C7—C6—H6	119.3
O1—C1—C2	122.58 (16)	C5—C6—H6	119.2
O2—C1—C2	113.77 (15)	C8—C7—C6	119.26 (16)
C1—C2—C3	113.83 (14)	C8—C7—H7	120.4
C1—C2—H2A	108.8	C6—C7—H7	120.3
C3—C2—H2A	108.8	O4—C8—C7	124.36 (17)
C1—C2—H2B	108.8	O4—C8—C9	115.40 (16)
C3—C2—H2B	108.7	C7—C8—C9	120.24 (16)
H2A—C2—H2B	107.6	C10—C9—C8	119.74 (16)
C4—C3—C2	112.19 (15)	C10—C9—H9	120.1
C4—C3—H3A	109.3	C8—C9—H9	120.2
C2—C3—H3A	109.2	C9—C10—C5	120.94 (16)
C4—C3—H3B	109.2	C9—C10—H10	119.5
C2—C3—H3B	109.1	C5—C10—H10	119.6
H3A—C3—H3B	107.9	O4—C11—H11A	109.5
O3—C4—C5	120.98 (15)	O4—C11—H11B	109.5
O3—C4—C3	120.04 (15)	H11A—C11—H11B	109.5
C5—C4—C3	118.98 (14)	O4—C11—H11C	109.4
C6—C5—C10	118.33 (15)	H11A—C11—H11C	109.5
C6—C5—C4	121.91 (15)	H11B—C11—H11C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.81	2.628 (3)	173
C6—H6···O3ii	0.93	2.34	3.247 (3)	164
C11—H11B···O4iii	0.96	2.60	3.328 (3)	133
C3—H3B···Cg1iv	0.97	2.74	3.591 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.81	2.628 (3)	173
C6—H6⋯O3ii	0.93	2.34	3.247 (3)	164
C11—H11B⋯O4iii	0.96	2.60	3.328 (3)	133
C3—H3B⋯Cg1iv	0.97	2.74	3.591 (3)	146

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the phenyl ring.