2-(4-Ethoxy-benzyl-idene)butanoic acid.

In the crystal structure of the title compound, C(13)H(16)O(3), dimers are formed due to inter-molecular O-H⋯O hydrogen bonding. There exists an intra-molecular C-H⋯O hydrogen bond which forms a five-membered ring. There is also present a C-H⋯π inter-action between a methyl CH group of an ethyl group and the centroid of the aromatic ring.

Related literature

For related literature, see: Bernstein et al. (1995 ▶); Burt (2004 ▶); Muhammad et al. (2007 ▶, 2008a ▶,b ▶,c ▶); Niaz et al. (2008 ▶).

Experimental

Crystal data

C13H16O3

M = 220.26

Monoclinic,

a = 10.3192 (7) Å

b = 22.0761 (15) Å

c = 5.2362 (3) Å

β = 100.751 (4)°

V = 1171.91 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 (2) K

0.26 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.985

13990 measured reflections

3009 independent reflections

1599 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.122

S = 1.00

3009 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802103X/at2588sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802103X/at2588Isup2.hkl

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

C13H16O3	F000 = 472
Mr = 220.26	Dx = 1.248 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3009 reflections
a = 10.3192 (7) Å	θ = 2.0–28.7º
b = 22.0761 (15) Å	µ = 0.09 mm−1
c = 5.2362 (3) Å	T = 296 (2) K
β = 100.751 (4)º	Prismatic, colourless
V = 1171.91 (13) Å3	0.26 × 0.20 × 0.16 mm
Z = 4

Bruker KappaAPEXII CCD diffractometer	3009 independent reflections
Radiation source: fine-focus sealed tube	1599 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.049
Detector resolution: 7.4 pixels mm-1	θmax = 28.7º
T = 296(2) K	θmin = 2.0º
ω scans	h = −13→13
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −29→29
Tmin = 0.975, Tmax = 0.985	l = −7→6
13990 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0465P)2 + 0.113P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3009 reflections	Δρmax = 0.15 e Å−3
150 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction coefficient: ?

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.62469 (12)	−0.00644 (5)	−0.2194 (2)	0.0545 (4)
O2	0.47639 (13)	0.06481 (5)	−0.3546 (2)	0.0577 (5)
O3	1.08170 (11)	0.17222 (5)	1.0247 (2)	0.0506 (4)
C1	0.82240 (15)	0.09272 (7)	0.4115 (3)	0.0388 (5)
C2	0.89602 (16)	0.05704 (7)	0.6035 (3)	0.0437 (6)
C3	0.98214 (17)	0.08106 (7)	0.8122 (3)	0.0447 (6)
C4	0.99847 (16)	0.14314 (7)	0.8316 (3)	0.0396 (5)
C5	0.92792 (17)	0.17994 (7)	0.6416 (3)	0.0457 (6)
C6	0.84164 (17)	0.15537 (7)	0.4371 (3)	0.0461 (6)
C7	0.73819 (16)	0.06338 (7)	0.1901 (3)	0.0420 (6)
C8	0.63076 (16)	0.08379 (7)	0.0301 (3)	0.0385 (5)
C9	0.57279 (17)	0.04572 (7)	−0.1946 (3)	0.0411 (5)
C10	0.55968 (18)	0.14224 (7)	0.0567 (3)	0.0456 (6)
C11	0.5866 (2)	0.19159 (8)	−0.1265 (3)	0.0613 (7)
C12	1.16254 (18)	0.13667 (8)	1.2209 (3)	0.0523 (6)
C13	1.2471 (2)	0.17960 (10)	1.4013 (4)	0.0696 (8)
H1	0.5832 (17)	−0.0279 (8)	−0.385 (4)	0.0654*
H2	0.88696	0.01518	0.59100	0.0525*
H3	1.02879	0.05571	0.93877	0.0537*
H5	0.93908	0.22172	0.65263	0.0548*
H6	0.79466	0.18098	0.31205	0.0553*
H7	0.76348	0.02428	0.15510	0.0503*
H10A	0.58522	0.15670	0.23393	0.0547*
H10B	0.46558	0.13434	0.02599	0.0547*
H11A	0.56467	0.17725	−0.30240	0.0919*
H11B	0.67825	0.20238	−0.08728	0.0919*
H11C	0.53385	0.22647	−0.10632	0.0919*
H12A	1.21722	0.10923	1.14239	0.0627*
H12B	1.10791	0.11292	1.31526	0.0627*
H13A	1.30278	0.20185	1.30692	0.1044*
H13B	1.30068	0.15718	1.53886	0.1044*
H13C	1.19191	0.20730	1.47359	0.1044*

	U11	U22	U33	U12	U13	U23
O1	0.0617 (9)	0.0404 (7)	0.0544 (7)	0.0025 (6)	−0.0076 (6)	−0.0162 (5)
O2	0.0623 (9)	0.0493 (8)	0.0515 (7)	0.0067 (6)	−0.0149 (7)	−0.0126 (6)
O3	0.0561 (8)	0.0421 (7)	0.0456 (7)	−0.0019 (6)	−0.0109 (6)	−0.0018 (5)
C1	0.0377 (10)	0.0378 (9)	0.0402 (9)	−0.0003 (7)	0.0053 (8)	−0.0036 (7)
C2	0.0484 (11)	0.0316 (9)	0.0501 (10)	−0.0018 (8)	0.0066 (9)	−0.0015 (7)
C3	0.0477 (11)	0.0397 (10)	0.0434 (10)	0.0012 (8)	−0.0002 (8)	0.0037 (7)
C4	0.0391 (10)	0.0395 (9)	0.0387 (9)	−0.0009 (8)	0.0034 (8)	−0.0049 (7)
C5	0.0504 (11)	0.0312 (9)	0.0507 (10)	−0.0010 (8)	−0.0027 (9)	−0.0027 (8)
C6	0.0481 (11)	0.0380 (9)	0.0470 (9)	0.0008 (8)	−0.0044 (8)	0.0016 (7)
C7	0.0478 (11)	0.0347 (9)	0.0430 (9)	−0.0017 (8)	0.0075 (8)	−0.0048 (7)
C8	0.0414 (10)	0.0367 (9)	0.0365 (9)	−0.0037 (8)	0.0053 (8)	−0.0042 (7)
C9	0.0444 (10)	0.0344 (9)	0.0433 (9)	−0.0038 (8)	0.0048 (8)	−0.0047 (7)
C10	0.0460 (11)	0.0468 (10)	0.0425 (9)	0.0009 (8)	0.0041 (8)	−0.0099 (8)
C11	0.0821 (15)	0.0456 (11)	0.0513 (11)	0.0044 (10)	−0.0003 (10)	−0.0010 (8)
C12	0.0490 (12)	0.0516 (11)	0.0507 (10)	0.0063 (9)	−0.0054 (9)	0.0003 (8)
C13	0.0603 (14)	0.0705 (14)	0.0663 (13)	0.0025 (11)	−0.0183 (11)	−0.0055 (11)

O1—C9	1.287 (2)	C12—C13	1.498 (3)
O2—C9	1.248 (2)	C2—H2	0.9300
O3—C4	1.3595 (19)	C3—H3	0.9300
O3—C12	1.431 (2)	C5—H5	0.9300
O1—H1	1.01 (2)	C6—H6	0.9300
C1—C2	1.387 (2)	C7—H7	0.9300
C1—C6	1.400 (2)	C10—H10A	0.9700
C1—C7	1.464 (2)	C10—H10B	0.9700
C2—C3	1.379 (2)	C11—H11A	0.9600
C3—C4	1.382 (2)	C11—H11B	0.9600
C4—C5	1.382 (2)	C11—H11C	0.9600
C5—C6	1.370 (2)	C12—H12A	0.9700
C7—C8	1.337 (2)	C12—H12B	0.9700
C8—C9	1.479 (2)	C13—H13A	0.9600
C8—C10	1.504 (2)	C13—H13B	0.9600
C10—C11	1.511 (2)	C13—H13C	0.9600
C4—O3—C12	118.54 (12)	C1—C6—H6	119.00
C9—O1—H1	112.9 (10)	C5—C6—H6	119.00
C2—C1—C6	116.29 (14)	C1—C7—H7	115.00
C6—C1—C7	124.44 (14)	C8—C7—H7	115.00
C2—C1—C7	119.13 (14)	C8—C10—H10A	109.00
C1—C2—C3	122.74 (14)	C8—C10—H10B	109.00
C2—C3—C4	119.41 (15)	C11—C10—H10A	109.00
O3—C4—C5	115.64 (14)	C11—C10—H10B	109.00
C3—C4—C5	119.30 (15)	H10A—C10—H10B	108.00
O3—C4—C3	125.05 (14)	C10—C11—H11A	109.00
C4—C5—C6	120.54 (14)	C10—C11—H11B	109.00
C1—C6—C5	121.71 (15)	C10—C11—H11C	109.00
C1—C7—C8	130.35 (15)	H11A—C11—H11B	109.00
C7—C8—C9	118.18 (14)	H11A—C11—H11C	109.00
C9—C8—C10	115.44 (14)	H11B—C11—H11C	109.00
C7—C8—C10	126.37 (14)	O3—C12—H12A	110.00
O1—C9—O2	121.94 (14)	O3—C12—H12B	110.00
O1—C9—C8	118.35 (14)	C13—C12—H12A	110.00
O2—C9—C8	119.72 (14)	C13—C12—H12B	110.00
C8—C10—C11	114.16 (15)	H12A—C12—H12B	109.00
O3—C12—C13	107.38 (15)	C12—C13—H13A	109.00
C1—C2—H2	119.00	C12—C13—H13B	109.00
C3—C2—H2	119.00	C12—C13—H13C	109.00
C2—C3—H3	120.00	H13A—C13—H13B	110.00
C4—C3—H3	120.00	H13A—C13—H13C	109.00
C4—C5—H5	120.00	H13B—C13—H13C	109.00
C6—C5—H5	120.00
C12—O3—C4—C3	2.0 (2)	O3—C4—C5—C6	179.67 (15)
C12—O3—C4—C5	−176.99 (14)	C3—C4—C5—C6	0.6 (3)
C4—O3—C12—C13	177.96 (14)	C4—C5—C6—C1	−0.5 (3)
C6—C1—C2—C3	1.2 (2)	C1—C7—C8—C9	174.19 (16)
C7—C1—C2—C3	177.04 (16)	C1—C7—C8—C10	−6.8 (3)
C2—C1—C6—C5	−0.4 (2)	C7—C8—C9—O1	3.1 (2)
C7—C1—C6—C5	−176.02 (16)	C7—C8—C9—O2	−176.51 (16)
C2—C1—C7—C8	156.09 (18)	C10—C8—C9—O1	−176.06 (14)
C6—C1—C7—C8	−28.4 (3)	C10—C8—C9—O2	4.4 (2)
C1—C2—C3—C4	−1.1 (3)	C7—C8—C10—C11	103.29 (19)
C2—C3—C4—O3	−178.82 (15)	C9—C8—C10—C11	−77.65 (19)
C2—C3—C4—C5	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	1.01 (2)	1.61 (2)	2.6184 (15)	176.8 (15)
C7—H7···O1	0.93	2.30	2.7218 (19)	107
C12—H12B···CgAii	0.96	2.82	3.6534 (19)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	1.01 (2)	1.61 (2)	2.6184 (15)	176.8 (15)
C7—H7⋯O1	0.93	2.30	2.7218 (19)	107
C12—H12B⋯CgAii	0.96	2.82	3.6534 (19)	145

Symmetry codes: (i) ; (ii) . CgA is the centroid of the C1–C6 ring.