Ethyl 3-benzoyl-2-hydroxy-prop-2-enoate.

In the title compound, C(12)H(12)O(4), the dihedral angle between the plane through the phenyl ring and the mean plane of the side chain is approximately 14°. The mol-ecules, which contain an intra-molecular O-H⋯O hydrogen bond, are linked end-to-end by weak C-H⋯O inter-molecular hydrogen-bonding contacts, forming infinite one-dimensional chain systems in the crystal structure.

Related literature

For related literature, see: Davey & Ribbons (1975 ▶); Emerson et al. (1991 ▶); Aliev et al. (2000a ▶,b ▶); Bernstein et al. (1995 ▶); Desiraju & Steiner (2001 ▶).

Experimental

Crystal data

C12H12O4

M = 220.22

Monoclinic,

a = 9.872 (4) Å

b = 13.498 (5) Å

c = 8.843 (3) Å

β = 105.464 (6)°

V = 1135.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 294 (2) K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.981

6252 measured reflections

2316 independent reflections

1405 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.151

S = 1.02

2316 reflections

147 parameters

2 restraints

H-atom parameters constraned

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807061223/si2049sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061223/si2049Isup2.hkl

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

C12H12O4	F000 = 464
Mr = 220.22	Dx = 1.288 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1800 reflections
a = 9.872 (4) Å	θ = 2.6–26.2º
b = 13.498 (5) Å	µ = 0.10 mm−1
c = 8.843 (3) Å	T = 294 (2) K
β = 105.464 (6)º	Block, yellow
V = 1135.7 (7) Å3	0.26 × 0.22 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2316 independent reflections
Radiation source: fine-focus sealed tube	1405 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
T = 294(2) K	θmax = 26.4º
phi and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.975, Tmax = 0.981	k = −16→15
6252 measured reflections	l = −9→10

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.0635P)2 + 0.3304P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2316 reflections	Δρmax = 0.20 e Å−3
147 parameters	Δρmin = −0.21 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.58450 (15)	0.67082 (13)	0.25001 (17)	0.0695 (5)
O2	0.43270 (15)	0.65232 (14)	0.43639 (17)	0.0714 (5)
H2A	0.4506	0.6651	0.3531	0.107*
O3	0.62879 (18)	0.56869 (16)	0.80268 (18)	0.0871 (6)
O4	0.40548 (14)	0.61835 (11)	0.71546 (15)	0.0558 (4)
C1	0.9543 (2)	0.62744 (16)	0.4355 (3)	0.0589 (6)
H1	0.9547	0.6290	0.5407	0.071*
C2	1.0792 (2)	0.6156 (2)	0.3952 (3)	0.0708 (7)
H2	1.1633	0.6099	0.4732	0.085*
C3	1.0797 (3)	0.61223 (19)	0.2404 (3)	0.0726 (7)
H3	1.1636	0.6025	0.2136	0.087*
C4	0.9558 (3)	0.6232 (2)	0.1241 (3)	0.0721 (7)
H4	0.9566	0.6216	0.0192	0.087*
C5	0.8304 (2)	0.63658 (17)	0.1634 (3)	0.0603 (6)
H5	0.7473	0.6453	0.0849	0.072*
C6	0.8285 (2)	0.63697 (14)	0.3204 (2)	0.0479 (5)
C7	0.6913 (2)	0.64484 (15)	0.3590 (2)	0.0490 (5)
C8	0.6759 (2)	0.62196 (16)	0.5096 (2)	0.0516 (5)
H8A	0.7552	0.6022	0.5926	0.062*
C9	0.5473 (2)	0.62671 (15)	0.5400 (2)	0.0497 (5)
C10	0.5333 (2)	0.60126 (17)	0.7012 (2)	0.0536 (5)
C11	0.3828 (2)	0.5971 (2)	0.8685 (2)	0.0641 (6)
H11A	0.4489	0.6341	0.9496	0.077*
H11B	0.3962	0.5270	0.8920	0.077*
C12	0.2353 (3)	0.6269 (2)	0.8617 (3)	0.0833 (8)
H12A	0.2239	0.6966	0.8405	0.125*
H12B	0.2164	0.6126	0.9604	0.125*
H12C	0.1710	0.5906	0.7799	0.125*

	U11	U22	U33	U12	U13	U23
O1	0.0472 (9)	0.1101 (13)	0.0500 (9)	0.0117 (8)	0.0109 (7)	0.0164 (9)
O2	0.0429 (9)	0.1209 (15)	0.0501 (9)	0.0102 (8)	0.0119 (7)	0.0166 (9)
O3	0.0623 (11)	0.1483 (18)	0.0514 (10)	0.0333 (11)	0.0161 (8)	0.0217 (10)
O4	0.0470 (8)	0.0774 (10)	0.0453 (8)	0.0045 (7)	0.0163 (6)	0.0043 (7)
C1	0.0463 (12)	0.0808 (16)	0.0507 (12)	0.0012 (11)	0.0151 (10)	0.0017 (11)
C2	0.0464 (13)	0.1006 (19)	0.0671 (15)	0.0019 (12)	0.0183 (11)	0.0075 (13)
C3	0.0546 (15)	0.0928 (19)	0.0803 (17)	0.0009 (13)	0.0353 (13)	0.0072 (14)
C4	0.0713 (17)	0.0946 (19)	0.0593 (14)	−0.0037 (13)	0.0326 (13)	0.0025 (13)
C5	0.0531 (13)	0.0767 (16)	0.0518 (13)	0.0000 (11)	0.0150 (10)	0.0068 (11)
C6	0.0455 (12)	0.0522 (12)	0.0480 (11)	−0.0005 (9)	0.0159 (9)	0.0019 (9)
C7	0.0419 (11)	0.0555 (12)	0.0492 (12)	0.0020 (9)	0.0117 (9)	−0.0019 (9)
C8	0.0420 (12)	0.0697 (14)	0.0424 (11)	0.0090 (9)	0.0101 (9)	0.0013 (10)
C9	0.0448 (11)	0.0597 (13)	0.0430 (11)	0.0042 (9)	0.0093 (9)	−0.0018 (9)
C10	0.0456 (12)	0.0693 (14)	0.0455 (12)	0.0050 (10)	0.0115 (10)	−0.0013 (10)
C11	0.0679 (15)	0.0823 (16)	0.0462 (12)	0.0021 (12)	0.0220 (11)	0.0012 (11)
C12	0.0776 (18)	0.104 (2)	0.0825 (18)	0.0151 (15)	0.0469 (15)	0.0085 (15)

O1—C7	1.274 (2)	C4—H4	0.9300
O2—C9	1.299 (2)	C5—C6	1.394 (3)
O2—H2A	0.8200	C5—H5	0.9300
O3—C10	1.199 (2)	C6—C7	1.486 (3)
O4—C10	1.321 (2)	C7—C8	1.415 (3)
O4—C11	1.458 (2)	C8—C9	1.367 (3)
C1—C2	1.381 (3)	C8—H8A	0.9572
C1—C6	1.386 (3)	C9—C10	1.509 (3)
C1—H1	0.9300	C11—C12	1.496 (3)
C2—C3	1.371 (3)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.380 (3)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.383 (3)	C12—H12C	0.9600
C9—O2—H2A	109.5	C8—C7—C6	122.28 (18)
C10—O4—C11	116.17 (16)	C9—C8—C7	120.88 (19)
C2—C1—C6	120.5 (2)	C9—C8—H8A	118.4
C2—C1—H1	119.7	C7—C8—H8A	120.8
C6—C1—H1	119.7	O2—C9—C8	123.66 (19)
C3—C2—C1	120.2 (2)	O2—C9—C10	116.41 (18)
C3—C2—H2	119.9	C8—C9—C10	119.93 (18)
C1—C2—H2	119.9	O3—C10—O4	125.0 (2)
C2—C3—C4	120.2 (2)	O3—C10—C9	122.62 (19)
C2—C3—H3	119.9	O4—C10—C9	112.41 (17)
C4—C3—H3	119.9	O4—C11—C12	107.37 (18)
C3—C4—C5	120.1 (2)	O4—C11—H11A	110.2
C3—C4—H4	119.9	C12—C11—H11A	110.2
C5—C4—H4	119.9	O4—C11—H11B	110.2
C4—C5—C6	120.1 (2)	C12—C11—H11B	110.2
C4—C5—H5	120.0	H11A—C11—H11B	108.5
C6—C5—H5	120.0	C11—C12—H12A	109.5
C1—C6—C5	118.92 (19)	C11—C12—H12B	109.5
C1—C6—C7	122.10 (19)	H12A—C12—H12B	109.5
C5—C6—C7	118.96 (19)	C11—C12—H12C	109.5
O1—C7—C8	119.81 (18)	H12A—C12—H12C	109.5
O1—C7—C6	117.88 (18)	H12B—C12—H12C	109.5
C6—C1—C2—C3	−0.6 (4)	O1—C7—C8—C9	0.4 (3)
C1—C2—C3—C4	1.7 (4)	C6—C7—C8—C9	−177.77 (19)
C2—C3—C4—C5	−0.7 (4)	C7—C8—C9—O2	−0.4 (3)
C3—C4—C5—C6	−1.3 (4)	C7—C8—C9—C10	179.55 (19)
C2—C1—C6—C5	−1.4 (3)	C11—O4—C10—O3	1.2 (3)
C2—C1—C6—C7	176.9 (2)	C11—O4—C10—C9	−179.21 (18)
C4—C5—C6—C1	2.3 (3)	O2—C9—C10—O3	173.6 (2)
C4—C5—C6—C7	−176.0 (2)	C8—C9—C10—O3	−6.3 (3)
C1—C6—C7—O1	167.8 (2)	O2—C9—C10—O4	−6.0 (3)
C5—C6—C7—O1	−13.9 (3)	C8—C9—C10—O4	174.08 (19)
C1—C6—C7—C8	−14.0 (3)	C10—O4—C11—C12	176.8 (2)
C5—C6—C7—C8	164.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.80	2.518 (2)	146
C5—H5···O3i	0.93	2.67	3.405 (3)	137
C11—H11A···O1ii	0.97	2.68	3.571 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.82	1.80	2.518 (2)	146
C5—H5⋯O3i	0.93	2.67	3.405 (3)	137
C11—H11A⋯O1ii	0.97	2.68	3.571 (4)	153

Symmetry codes: (i) ; (ii) .