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

The title compound, C(12)H(14)O(4), is an important inter-mediate in the synthesis of biologically active heterocyclic compounds. In the crystal structure, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules. There are also C-H⋯π contacts between the benzene ring and the methyl-ene groups.

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

C12H14O4

M = 222.23

Triclinic,

a = 7.8371 (3) Å

b = 8.7399 (5) Å

c = 9.8140 (5) Å

α = 106.993 (4)°

β = 107.541 (4)°

γ = 107.142 (4)°

V = 556.34 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 150 (1) K

0.34 × 0.32 × 0.31 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer

Absorption correction: Gaussian (Coppens, 1970 ▶) T min = 0.964, T max = 0.987

8993 measured reflections

2508 independent reflections

2089 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 1.11

2508 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 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/S1600536808034429/hk2555sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034429/hk2555Isup2.hkl

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

C12H14O4	Z = 2
Mr = 222.23	F(000) = 236
Triclinic, P1	Dx = 1.327 Mg m−3
Hall symbol: -P 1	Melting point: 404(1) K
a = 7.8371 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7399 (5) Å	Cell parameters from 9044 reflections
c = 9.8140 (5) Å	θ = 1–27.5°
α = 106.993 (4)°	µ = 0.10 mm−1
β = 107.541 (4)°	T = 150 K
γ = 107.142 (4)°	Block, colorless
V = 556.34 (6) Å3	0.34 × 0.32 × 0.31 mm

Bruker–Nonius KappaCCD area-detector diffractometer	2508 independent reflections
Radiation source: fine-focus sealed tube	2089 reflections with I > 2σ(I)
graphite	Rint = 0.059
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.4°
φ and ω scans	h = −10→10
Absorption correction: gaussian (Coppens, 1970)	k = −11→11
Tmin = 0.964, Tmax = 0.987	l = −12→12
8993 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.2871P] where P = (Fo2 + 2Fc2)/3
2508 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.24 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	0.19232 (17)	0.45879 (16)	0.01166 (16)	0.0387 (3)
O2	−0.11942 (17)	0.27131 (16)	−0.14840 (16)	0.0419 (3)
H2	−0.1388	0.3584	−0.1118	0.050*
O3	0.21830 (18)	0.16047 (18)	0.13387 (15)	0.0373 (3)
O4	1.07552 (17)	0.25792 (17)	0.51668 (14)	0.0352 (3)
C1	0.0717 (2)	0.3129 (2)	−0.08709 (19)	0.0287 (3)
C2	0.1221 (2)	0.1655 (2)	−0.15467 (19)	0.0295 (3)
H2A	0.1061	0.1493	−0.2606	0.035*
H2B	0.0308	0.0577	−0.1615	0.035*
C3	0.3310 (2)	0.1968 (2)	−0.05809 (19)	0.0279 (3)
H3A	0.4210	0.3134	−0.0364	0.033*
H3B	0.3658	0.1115	−0.1184	0.033*
C4	0.3542 (2)	0.1827 (2)	0.09544 (18)	0.0261 (3)
C5	0.5470 (2)	0.1981 (2)	0.19915 (18)	0.0258 (3)
C6	0.5593 (2)	0.1507 (2)	0.32477 (19)	0.0302 (4)
H6	0.4458	0.1043	0.3385	0.036*
C7	0.7366 (3)	0.1717 (2)	0.4281 (2)	0.0322 (4)
H7	0.7427	0.1394	0.5111	0.039*
C8	0.9075 (2)	0.2414 (2)	0.40859 (19)	0.0293 (3)
C9	0.8975 (2)	0.2867 (2)	0.2828 (2)	0.0326 (4)
H9	1.0105	0.3314	0.2679	0.039*
C10	0.7176 (2)	0.2637 (2)	0.1798 (2)	0.0306 (4)
H10	0.7107	0.2933	0.0952	0.037*
C11	1.2575 (2)	0.3431 (2)	0.5103 (2)	0.0338 (4)
H11A	1.2781	0.4618	0.5209	0.041*
H11B	1.2554	0.2783	0.4105	0.041*
C12	1.4192 (3)	0.3482 (3)	0.6432 (2)	0.0424 (4)
H12A	1.4192	0.4118	0.7412	0.051*
H12B	1.5439	0.4059	0.6429	0.051*
H12C	1.3981	0.2300	0.6308	0.051*

	U11	U22	U33	U12	U13	U23
O1	0.0274 (6)	0.0308 (6)	0.0479 (8)	0.0141 (5)	0.0076 (5)	0.0101 (6)
O2	0.0270 (6)	0.0365 (7)	0.0490 (8)	0.0156 (5)	0.0077 (6)	0.0076 (6)
O3	0.0318 (6)	0.0519 (8)	0.0351 (7)	0.0193 (6)	0.0182 (5)	0.0212 (6)
O4	0.0299 (6)	0.0454 (7)	0.0319 (6)	0.0157 (5)	0.0100 (5)	0.0213 (6)
C1	0.0257 (8)	0.0316 (8)	0.0305 (8)	0.0125 (7)	0.0099 (7)	0.0170 (7)
C2	0.0294 (8)	0.0327 (8)	0.0249 (8)	0.0138 (7)	0.0094 (6)	0.0116 (6)
C3	0.0294 (8)	0.0308 (8)	0.0278 (8)	0.0166 (7)	0.0129 (7)	0.0130 (7)
C4	0.0292 (8)	0.0233 (7)	0.0267 (8)	0.0121 (6)	0.0132 (6)	0.0091 (6)
C5	0.0297 (8)	0.0256 (7)	0.0248 (8)	0.0144 (6)	0.0118 (6)	0.0110 (6)
C6	0.0321 (8)	0.0338 (8)	0.0308 (8)	0.0157 (7)	0.0172 (7)	0.0155 (7)
C7	0.0369 (9)	0.0364 (9)	0.0290 (8)	0.0169 (7)	0.0154 (7)	0.0178 (7)
C8	0.0311 (8)	0.0295 (8)	0.0272 (8)	0.0151 (7)	0.0095 (7)	0.0122 (7)
C9	0.0293 (8)	0.0389 (9)	0.0347 (9)	0.0145 (7)	0.0156 (7)	0.0197 (8)
C10	0.0322 (8)	0.0382 (9)	0.0286 (8)	0.0170 (7)	0.0146 (7)	0.0192 (7)
C11	0.0305 (8)	0.0383 (9)	0.0297 (9)	0.0135 (7)	0.0103 (7)	0.0141 (7)
C12	0.0325 (9)	0.0505 (11)	0.0374 (10)	0.0138 (8)	0.0088 (8)	0.0196 (9)

O2—H2	0.8200	C5—C10	1.384 (2)
O3—C4	1.2156 (19)	C6—C7	1.373 (2)
O4—C8	1.3552 (19)	C6—H6	0.9300
O4—C11	1.431 (2)	C7—H7	0.9300
C1—O1	1.214 (2)	C8—C7	1.394 (2)
C1—O2	1.3210 (19)	C8—C9	1.390 (2)
C1—C2	1.488 (2)	C9—H9	0.9300
C2—H2A	0.9700	C10—C9	1.381 (2)
C2—H2B	0.9701	C10—H10	0.9300
C3—C2	1.517 (2)	C11—C12	1.500 (2)
C3—C4	1.508 (2)	C11—H11A	0.9700
C3—H3A	0.9700	C11—H11B	0.9700
C3—H3B	0.9700	C12—H12A	0.9599
C5—C4	1.487 (2)	C12—H12B	0.9600
C5—C6	1.397 (2)	C12—H12C	0.9600
C1—O2—H2	109.5	C5—C6—H6	119.6
C8—O4—C11	117.96 (13)	C6—C7—C8	120.05 (15)
O1—C1—O2	122.54 (15)	C6—C7—H7	120.0
O1—C1—C2	124.21 (14)	C8—C7—H7	120.0
O2—C1—C2	113.22 (14)	O4—C8—C9	124.30 (15)
C1—C2—C3	112.93 (14)	O4—C8—C7	115.80 (14)
C1—C2—H2A	109.0	C9—C8—C7	119.89 (15)
C3—C2—H2A	109.0	C10—C9—C8	119.16 (15)
C1—C2—H2B	109.0	C10—C9—H9	120.4
C3—C2—H2B	108.9	C8—C9—H9	120.4
H2A—C2—H2B	107.8	C9—C10—C5	121.76 (15)
C4—C3—C2	111.95 (13)	C9—C10—H10	119.2
C4—C3—H3A	109.1	C5—C10—H10	119.1
C2—C3—H3A	109.1	O4—C11—C12	107.39 (14)
C4—C3—H3B	109.4	O4—C11—H11A	110.2
C2—C3—H3B	109.4	C12—C11—H11A	110.3
H3A—C3—H3B	107.9	O4—C11—H11B	110.3
O3—C4—C5	120.78 (14)	C12—C11—H11B	110.2
O3—C4—C3	120.57 (14)	H11A—C11—H11B	108.5
C5—C4—C3	118.65 (13)	C11—C12—H12A	109.4
C10—C5—C6	118.30 (15)	C11—C12—H12B	109.5
C10—C5—C4	122.60 (14)	H12A—C12—H12B	109.5
C6—C5—C4	119.06 (14)	C11—C12—H12C	109.5
C7—C6—C5	120.82 (15)	H12A—C12—H12C	109.5
C7—C6—H6	119.6	H12B—C12—H12C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.85	2.664 (3)	172
C2—H2B···O3ii	0.97	2.44	3.386 (3)	165
C11—H11B···O3iii	0.97	2.50	3.445 (3)	166
C3—H3B···Cg1iv	0.97	2.66	3.528 (3)	150
C11—H11A···Cg1v	0.97	2.84	3.679 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.85	2.664 (3)	172
C2—H2B⋯O3ii	0.97	2.44	3.386 (3)	165
C11—H11B⋯O3iii	0.97	2.50	3.445 (3)	166
C3—H3B⋯Cg1iv	0.97	2.66	3.528 (3)	150
C11—H11A⋯Cg1v	0.97	2.84	3.679 (3)	145

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