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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o15
https://doi.org/10.1107/S1600536807061223

Ethyl 3-benzoyl-2-hy­droxy­prop-2-enoate

Jian Wang,a Wen Zhoub and Wen-Gui Xua*

aKey Laboratory of Tumor Prevention and Therapy, Tianjin Medical University Cancer Institute and Hospital PET–CT, Tianjin 300071, People's Republic of China, and bSchool of Pharmaceutical Sciences, Tianjin Medical University, Tianjin 300071, People's Republic of China
*Correspondence e-mail: wwbzzl@yahoo.com.cn

(Received 3 November 2007; accepted 20 November 2007; online 6 December 2007)

In the title compound, C12H12O4, the dihedral angle between the plane through the phenyl ring and the mean plane of the side chain is approximately 14°. The mol­ecules, which contain an intra­molecular O—H⋯O hydrogen bond, are linked end-to-end by weak C—H⋯O inter­molecular hydrogen-bonding contacts, forming infinite one-dimensional chain systems in the crystal structure.

Related literature

For related literature, see: Davey & Ribbons (1975[Davey, J. F. & Ribbons, D. W. (1975). J. Biol. Chem. 250, 3826-3830.]); Emerson et al. (1991[Emerson, D. W., Titus, R. L. & Gonzáles, R. M. (1991). J. Org. Chem. 56, 5301-5307.]); Aliev et al. (2000a[Aliev, Z. G., Shurov, S. N., Nekrasov, D. D., Podvintsev, I. B. & Atovmyan, L. O. (2000a). Zh. Strukt. Khim. 41, 1255-1260.],b[Aliev, Z. G., Shurov, S. N., Nekrasov, D. D., Podvintsev, I. B. & Atovmyan, L. O. (2000b). J. Struct. Chem, 41, 1041-1045.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Desiraju & Steiner (2001[Desiraju, G. R. & Steiner, T. (2001). The Weak Hydrogen Bond in Structural Chemistry and Biology, pp. 100-112. IUCr Monograph on Crystallography 9. Oxford University Press.]).

[Scheme 1]

Experimental

Crystal data

  • C12H12O4

  • Mr = 220.22

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.981

  • 6252 measured reflections

  • 2316 independent reflections

  • 1405 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 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

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) x, y, z-1; (ii) x, y, z+1.

Data collection: SMART (Bruker, 1998[Bruker, (1998). SMART-NT and SAINT-NT. Version 5.1. Bruker AXS Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker, (1998). SMART-NT and SAINT-NT. Version 5.1. Bruker AXS Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061223/si2049Isup2.hkl

checkCIF report


Comment top

1,3-Diketones are substrates for carbon-carbon bond hydrolysis by beta-ketolases. The 2,4-diketo acids examined for hydrolysis by acetopyruvate hydrolase from rat liver (EC 3.7.1.5) all have aliphatic side chains.(Davey & Ribbons, 1975) The acetopyruvate hydrolases cleave 2,4-diketopentanoic acid into pyruvate and acetate (Emerson et al., 1991). Cleavage of analogues such as 2,4-diketo-4-phenylbutanoic acid was not reported. In order to discover the hydrolysis process of analogues, the title compound was synthesized.

In the title compound, the C—O and C—C bond lengths are in the normal range, and the dihedral angle between the plane of the phenyl ring and the mean plane of the side chain is approximately 14 °. The corresponding torsion angle C1—C6—C7—C8 is -14.0 (3) °. The molecule contains the typical O—H···O intra-molecular hydrogen bond graph set S(6) (Bernstein et al., 1995). As shown in Figure 2, these monomers are associated end-to-end to form the R22(10) ring system, which is generated by different weak C—H···O hydrogen bonds (Table 1). These hydrogen bonds connect the molecules due to translational symmetry to assembly a chain system along the c direction. Similarly, the S(6) intra-molecular hydrogen bond type is also observed in 2-hydroxy-4-oxo-4-phenyl-3(Z)-butenic acid and 4-hydroxy-2-oxo-6-phenyl-3(Z),5(E)-hexadienic acid, but the monomer of the former is extended by the R22(8) (Bernstein et al. 1995) inter-molecular H-bonds, related by a centre of inversion to form a two-dimensional layer with head-to-tail packing architecture (Aliev et al., 2000a,b). Head-to-tail packing is also observed in the structure of the title compound, and long H···O distances (Table 1) in weak intermolecular C—H···O contacts are extensively discussed in the literature (Desiraju & Steiner, 2001).

Related literature top

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

Experimental top

Sodium (2.3 g, 103 mmol) was added to absolute ethanol (133 ml). The mixture was cooled to -273 K and a mixture of diethyl oxalate (14.0 g, 96 mmol) and the ketone (96 mmol) was added slowly over a period of 20 min. A precipitate formed and stirring was continued for 4 h at room temperature. The precipitate was filtered, washed with absolute ethanol (20 ml) and dissolved in 2 N sulfuric acid (150 ml) and ether-extracted (3x150 ml), dried over Na2SO4 and ether removed. The residue was distilled under reduced pressure. The residue was recrystallized from ethanol and single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from acetone at room temperature. Elemental analysis (%) calcd for 1, C18H22CuN4O8: C 65.45, H 5.49; found: C 65.52, H 5.54.

Refinement top

H atoms were positioned geometrically and treated as riding with distances C–H = 0.93–0.97 Å, and O–H = 0.82 Å. The respective Uiso(H)=1.2Ueq(aromatic C and CH2), Uiso(H)=1.5Ueq(CH3), Uiso(H)=1.5(Ueq)(hydroxyl O).

Structure description top

1,3-Diketones are substrates for carbon-carbon bond hydrolysis by beta-ketolases. The 2,4-diketo acids examined for hydrolysis by acetopyruvate hydrolase from rat liver (EC 3.7.1.5) all have aliphatic side chains.(Davey & Ribbons, 1975) The acetopyruvate hydrolases cleave 2,4-diketopentanoic acid into pyruvate and acetate (Emerson et al., 1991). Cleavage of analogues such as 2,4-diketo-4-phenylbutanoic acid was not reported. In order to discover the hydrolysis process of analogues, the title compound was synthesized.

In the title compound, the C—O and C—C bond lengths are in the normal range, and the dihedral angle between the plane of the phenyl ring and the mean plane of the side chain is approximately 14 °. The corresponding torsion angle C1—C6—C7—C8 is -14.0 (3) °. The molecule contains the typical O—H···O intra-molecular hydrogen bond graph set S(6) (Bernstein et al., 1995). As shown in Figure 2, these monomers are associated end-to-end to form the R22(10) ring system, which is generated by different weak C—H···O hydrogen bonds (Table 1). These hydrogen bonds connect the molecules due to translational symmetry to assembly a chain system along the c direction. Similarly, the S(6) intra-molecular hydrogen bond type is also observed in 2-hydroxy-4-oxo-4-phenyl-3(Z)-butenic acid and 4-hydroxy-2-oxo-6-phenyl-3(Z),5(E)-hexadienic acid, but the monomer of the former is extended by the R22(8) (Bernstein et al. 1995) inter-molecular H-bonds, related by a centre of inversion to form a two-dimensional layer with head-to-tail packing architecture (Aliev et al., 2000a,b). Head-to-tail packing is also observed in the structure of the title compound, and long H···O distances (Table 1) in weak intermolecular C—H···O contacts are extensively discussed in the literature (Desiraju & Steiner, 2001).

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

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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).

Figures top
[Figure 1] Fig. 1. An ORTEP view of the labelled title molecule with 30% thermal ellipsoids. The intramolecular hydrogen bond is indicated by a dashed line.
[Figure 2] Fig. 2. View of the one-dimensional weak hydrogen bonded chain structure.
Ethyl 3-benzoyl-2-hydroxyprop-2-enoate top
Crystal data top
C12H12O4F(000) = 464
Mr = 220.22Dx = 1.288 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1800 reflections
a = 9.872 (4) Åθ = 2.6–26.2°
b = 13.498 (5) ŵ = 0.10 mm−1
c = 8.843 (3) ÅT = 294 K
β = 105.464 (6)°Block, yellow
V = 1135.7 (7) Å30.26 × 0.22 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2316 independent reflections
Radiation source: fine-focus sealed tube1405 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
phi and ω scansθmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→11
Tmin = 0.975, Tmax = 0.981k = −16→15
6252 measured reflectionsl = −9→10
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0635P)2 + 0.3304P]
where P = (Fo2 + 2Fc2)/3
2316 reflections(Δ/σ)max < 0.001
147 parametersΔρmax = 0.20 e Å−3
2 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C12H12O4V = 1135.7 (7) Å3
Mr = 220.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.872 (4) ŵ = 0.10 mm−1
b = 13.498 (5) ÅT = 294 K
c = 8.843 (3) Å0.26 × 0.22 × 0.20 mm
β = 105.464 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2316 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1405 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.981Rint = 0.028
6252 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0492 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.02Δρmax = 0.20 e Å−3
2316 reflectionsΔρmin = −0.21 e Å−3
147 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.58450 (15)0.67082 (13)0.25001 (17)0.0695 (5)
O20.43270 (15)0.65232 (14)0.43639 (17)0.0714 (5)
H2A0.45060.66510.35310.107*
O30.62879 (18)0.56869 (16)0.80268 (18)0.0871 (6)
O40.40548 (14)0.61835 (11)0.71546 (15)0.0558 (4)
C10.9543 (2)0.62744 (16)0.4355 (3)0.0589 (6)
H10.95470.62900.54070.071*
C21.0792 (2)0.6156 (2)0.3952 (3)0.0708 (7)
H21.16330.60990.47320.085*
C31.0797 (3)0.61223 (19)0.2404 (3)0.0726 (7)
H31.16360.60250.21360.087*
C40.9558 (3)0.6232 (2)0.1241 (3)0.0721 (7)
H40.95660.62160.01920.087*
C50.8304 (2)0.63658 (17)0.1634 (3)0.0603 (6)
H50.74730.64530.08490.072*
C60.8285 (2)0.63697 (14)0.3204 (2)0.0479 (5)
C70.6913 (2)0.64484 (15)0.3590 (2)0.0490 (5)
C80.6759 (2)0.62196 (16)0.5096 (2)0.0516 (5)
H8A0.75520.60220.59260.062*
C90.5473 (2)0.62671 (15)0.5400 (2)0.0497 (5)
C100.5333 (2)0.60126 (17)0.7012 (2)0.0536 (5)
C110.3828 (2)0.5971 (2)0.8685 (2)0.0641 (6)
H11A0.44890.63410.94960.077*
H11B0.39620.52700.89200.077*
C120.2353 (3)0.6269 (2)0.8617 (3)0.0833 (8)
H12A0.22390.69660.84050.125*
H12B0.21640.61260.96040.125*
H12C0.17100.59060.77990.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0472 (9)0.1101 (13)0.0500 (9)0.0117 (8)0.0109 (7)0.0164 (9)
O20.0429 (9)0.1209 (15)0.0501 (9)0.0102 (8)0.0119 (7)0.0166 (9)
O30.0623 (11)0.1483 (18)0.0514 (10)0.0333 (11)0.0161 (8)0.0217 (10)
O40.0470 (8)0.0774 (10)0.0453 (8)0.0045 (7)0.0163 (6)0.0043 (7)
C10.0463 (12)0.0808 (16)0.0507 (12)0.0012 (11)0.0151 (10)0.0017 (11)
C20.0464 (13)0.1006 (19)0.0671 (15)0.0019 (12)0.0183 (11)0.0075 (13)
C30.0546 (15)0.0928 (19)0.0803 (17)0.0009 (13)0.0353 (13)0.0072 (14)
C40.0713 (17)0.0946 (19)0.0593 (14)−0.0037 (13)0.0326 (13)0.0025 (13)
C50.0531 (13)0.0767 (16)0.0518 (13)0.0000 (11)0.0150 (10)0.0068 (11)
C60.0455 (12)0.0522 (12)0.0480 (11)−0.0005 (9)0.0159 (9)0.0019 (9)
C70.0419 (11)0.0555 (12)0.0492 (12)0.0020 (9)0.0117 (9)−0.0019 (9)
C80.0420 (12)0.0697 (14)0.0424 (11)0.0090 (9)0.0101 (9)0.0013 (10)
C90.0448 (11)0.0597 (13)0.0430 (11)0.0042 (9)0.0093 (9)−0.0018 (9)
C100.0456 (12)0.0693 (14)0.0455 (12)0.0050 (10)0.0115 (10)−0.0013 (10)
C110.0679 (15)0.0823 (16)0.0462 (12)0.0021 (12)0.0220 (11)0.0012 (11)
C120.0776 (18)0.104 (2)0.0825 (18)0.0151 (15)0.0469 (15)0.0085 (15)
Geometric parameters (Å, º) top
O1—C71.274 (2)C4—H40.9300
O2—C91.299 (2)C5—C61.394 (3)
O2—H2A0.8200C5—H50.9300
O3—C101.199 (2)C6—C71.486 (3)
O4—C101.321 (2)C7—C81.415 (3)
O4—C111.458 (2)C8—C91.367 (3)
C1—C21.381 (3)C8—H8A0.9572
C1—C61.386 (3)C9—C101.509 (3)
C1—H10.9300C11—C121.496 (3)
C2—C31.371 (3)C11—H11A0.9700
C2—H20.9300C11—H11B0.9700
C3—C41.380 (3)C12—H12A0.9600
C3—H30.9300C12—H12B0.9600
C4—C51.383 (3)C12—H12C0.9600
C9—O2—H2A109.5C8—C7—C6122.28 (18)
C10—O4—C11116.17 (16)C9—C8—C7120.88 (19)
C2—C1—C6120.5 (2)C9—C8—H8A118.4
C2—C1—H1119.7C7—C8—H8A120.8
C6—C1—H1119.7O2—C9—C8123.66 (19)
C3—C2—C1120.2 (2)O2—C9—C10116.41 (18)
C3—C2—H2119.9C8—C9—C10119.93 (18)
C1—C2—H2119.9O3—C10—O4125.0 (2)
C2—C3—C4120.2 (2)O3—C10—C9122.62 (19)
C2—C3—H3119.9O4—C10—C9112.41 (17)
C4—C3—H3119.9O4—C11—C12107.37 (18)
C3—C4—C5120.1 (2)O4—C11—H11A110.2
C3—C4—H4119.9C12—C11—H11A110.2
C5—C4—H4119.9O4—C11—H11B110.2
C4—C5—C6120.1 (2)C12—C11—H11B110.2
C4—C5—H5120.0H11A—C11—H11B108.5
C6—C5—H5120.0C11—C12—H12A109.5
C1—C6—C5118.92 (19)C11—C12—H12B109.5
C1—C6—C7122.10 (19)H12A—C12—H12B109.5
C5—C6—C7118.96 (19)C11—C12—H12C109.5
O1—C7—C8119.81 (18)H12A—C12—H12C109.5
O1—C7—C6117.88 (18)H12B—C12—H12C109.5
C6—C1—C2—C3−0.6 (4)O1—C7—C8—C90.4 (3)
C1—C2—C3—C41.7 (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—C10179.55 (19)
C2—C1—C6—C5−1.4 (3)C11—O4—C10—O31.2 (3)
C2—C1—C6—C7176.9 (2)C11—O4—C10—C9−179.21 (18)
C4—C5—C6—C12.3 (3)O2—C9—C10—O3173.6 (2)
C4—C5—C6—C7−176.0 (2)C8—C9—C10—O3−6.3 (3)
C1—C6—C7—O1167.8 (2)O2—C9—C10—O4−6.0 (3)
C5—C6—C7—O1−13.9 (3)C8—C9—C10—O4174.08 (19)
C1—C6—C7—C8−14.0 (3)C10—O4—C11—C12176.8 (2)
C5—C6—C7—C8164.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O10.821.802.518 (2)146
C5—H5···O3i0.932.673.405 (3)137
C11—H11A···O1ii0.972.683.571 (4)153
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC12H12O4
Mr220.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)9.872 (4), 13.498 (5), 8.843 (3)
β (°) 105.464 (6)
V (Å3)1135.7 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.26 × 0.22 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.975, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections		6252, 2316, 1405
Rint0.028
(sin θ/λ)max (Å−1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.151, 1.02
No. of reflections2316
No. of parameters147
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.20, −0.21

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O10.821.802.518 (2)146
C5—H5···O3i0.932.673.405 (3)137
C11—H11A···O1ii0.972.683.571 (4)153
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1.
 

Acknowledgements

This work was supported by Tianjin Natural Science Foundation (No. 07JCYBJC09300).

References

First citationAliev, Z. G., Shurov, S. N., Nekrasov, D. D., Podvintsev, I. B. & Atovmyan, L. O. (2000a). Zh. Strukt. Khim. 41, 1255–1260.  Google Scholar
 First citationAliev, Z. G., Shurov, S. N., Nekrasov, D. D., Podvintsev, I. B. & Atovmyan, L. O. (2000b). J. Struct. Chem, 41, 1041–1045.  Web of Science CrossRef CAS Google Scholar
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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o15
https://doi.org/10.1107/S1600536807061223
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