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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 67| Part 10| October 2011| Page o2682
https://doi.org/10.1107/S1600536811037500

2-(4-Chloro­phen­yl)-2-oxo­ethyl 4-hy­dr­oxy­benzoate

Hoong-Kun Fun,a*‡ Tara Shahani,a B. Garudachari,b Arun M. Isloorb and Kammasandra N. Shivanandac

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bMedicinal Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and cSchulich Faculty of Chemistry, Technion Israel Institute of Technology, Haifa, Israel 32000
*Correspondence e-mail: hkfun@usm.my

(Received 14 September 2011; accepted 14 September 2011; online 17 September 2011)

The title compound, C15H11ClO4, consists of a chloro­benzene ring and a phenol ring which are linked together by a 1,4-dioxo-2-oxabutane-1,4-diyl group. The dihedral angle between the chloro­benzene and phenol rings is 65.70 (11)°. In the crystal, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains along [010].

Related literature

For background to phenacyl benzoate, see: Sheehan & Umezaw (1973[Sheehan, J. C. & Umezaw, K. (1973). J. Org. Chem. 58, 3771-3773.]); Gandhi et al. (1995[Gandhi, S. S., Bell, K. L. & Gibson, M. S. (1995). Tetrahedron, 51, 13301-13308.]); Huang et al. (1996[Huang, W., Pian, J., Chen, B., Pei, W. & Ye, X. (1996). Tetrahedron, 52, 10131-10136.]); Ruzicka et al. (2002[Ruzicka, R., Zabadal, M. & Klan, P. (2002). Synth. Commun. 32, 2581-2590.]); Litera et al. (2006[Litera, J. K., Loya, A. D. & Klan, P. (2006). J. Org. Chem. 71, 713-723.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C15H11ClO4

  • Mr = 290.69

  • Monoclinic, P 21

  • a = 5.5307 (10) Å

  • b = 8.1324 (15) Å

  • c = 14.857 (2) Å

  • β = 95.120 (4)°

  • V = 665.57 (19) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 296 K

  • 0.56 × 0.23 × 0.07 mm
Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wiscosin, USA.]) Tmin = 0.852, Tmax = 0.981

  • 6399 measured reflections

  • 3571 independent reflections

  • 2457 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.106

  • S = 1.02

  • 3571 reflections

  • 186 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.21 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1511 Friedel pairs

  • Flack parameter: −0.20 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O4—H1O4⋯O3i 0.78 (4) 2.01 (4) 2.783 (3) 168 (3)
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wiscosin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wiscosin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811037500/bq2305sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037500/bq2305Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037500/bq2305Isup3.cml

checkCIF report


Comment top

Phenacyl benzoate is a derivative of an acid formed by reaction between an acid and phenacyl bromide. These compounds find applications in the field of synthetic chemistry (Huang et al., 1996; Gandhi et al., 1995) such as in the synthesis of oxazoles, imidazoles, and benzoxazepines. They are also useful for photo-removable protecting groups for carboxylic acids in organic synthesis and biochemistry (Ruzicka et al., 2002; Litera et al., 2006; Sheehan & Umezaw, 1973). Keeping this in view, the title compound was synthesized to study its crystal structure.

The title compound, (Fig. 1), consists of a chlorobenzene (Cl1/C1–C6) ring and a phenol(O4/C10–C15) ring which are linked together by a 2-oxopropyl acetate (C7–C9/O1–O3) group. The dihedral angle formed between the chlorobenzene and a phenol ring is 65.70 (11) °. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal packing (Fig. 2), intermolecular O4—H1O4···O3 hydrogen bonds (Table 1) link the molecules in one-dimensional chains along [010].

Related literature top

For background to phenacyl benzoate, see: Sheehan & Umezaw (1973); Gandhi et al. (1995); Huang et al. (1996); Ruzicka et al. (2002); Litera et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

The mixture of 4-hydroxybenzoic acid (1.0 g, 0.0072 mol), potassium carbonate (1.10 g, 0.0079 mol) and 2-bromo-1-(4-chlorophenyl)ethanone (1.68 g, 0.0072 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colorless needle-shaped 2-(4-chlorophenyl)-2-oxoethyl 4-hydroxybenzoate begin to separate out. It was collected by filtration and recrystallized from ethanol. Yield: 1.95 g, 92.8%, M.p: 453–454 K.

Refinement top

The hydrogen atoms bound to C atoms were positioned geometrically [C–H = 0.9300–0.9700 Å] with Uiso(H) = 1.2. The hydrogen atoms attached to the O atom was located from the difference map and refined freely, [O–H = 0.79 (3) Å].

Structure description top

Phenacyl benzoate is a derivative of an acid formed by reaction between an acid and phenacyl bromide. These compounds find applications in the field of synthetic chemistry (Huang et al., 1996; Gandhi et al., 1995) such as in the synthesis of oxazoles, imidazoles, and benzoxazepines. They are also useful for photo-removable protecting groups for carboxylic acids in organic synthesis and biochemistry (Ruzicka et al., 2002; Litera et al., 2006; Sheehan & Umezaw, 1973). Keeping this in view, the title compound was synthesized to study its crystal structure.

The title compound, (Fig. 1), consists of a chlorobenzene (Cl1/C1–C6) ring and a phenol(O4/C10–C15) ring which are linked together by a 2-oxopropyl acetate (C7–C9/O1–O3) group. The dihedral angle formed between the chlorobenzene and a phenol ring is 65.70 (11) °. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal packing (Fig. 2), intermolecular O4—H1O4···O3 hydrogen bonds (Table 1) link the molecules in one-dimensional chains along [010].

For background to phenacyl benzoate, see: Sheehan & Umezaw (1973); Gandhi et al. (1995); Huang et al. (1996); Ruzicka et al. (2002); Litera et al. (2006). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the a axis, showing a one-dimensional chain along [010].
2-(4-Chlorophenyl)-2-oxoethyl 4-hydroxybenzoate top
Crystal data top
C15H11ClO4F(000) = 300
Mr = 290.69Dx = 1.450 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1832 reflections
a = 5.5307 (10) Åθ = 3.7–24.1°
b = 8.1324 (15) ŵ = 0.30 mm−1
c = 14.857 (2) ÅT = 296 K
β = 95.120 (4)°Plate, colourless
V = 665.57 (19) Å30.56 × 0.23 × 0.07 mm
Z = 2
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer		3571 independent reflections
Radiation source: fine-focus sealed tube2457 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 30.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −5→7
Tmin = 0.852, Tmax = 0.981k = −11→11
6399 measured reflectionsl = −20→20
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0346P)2 + 0.0709P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3571 reflectionsΔρmax = 0.20 e Å−3
186 parametersΔρmin = −0.21 e Å−3
1 restraintAbsolute structure: Flack (1983), 1511 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: −0.20 (8)
Crystal data top
C15H11ClO4V = 665.57 (19) Å3
Mr = 290.69Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.5307 (10) ŵ = 0.30 mm−1
b = 8.1324 (15) ÅT = 296 K
c = 14.857 (2) Å0.56 × 0.23 × 0.07 mm
β = 95.120 (4)°
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer		3571 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2457 reflections with I > 2σ(I)
Tmin = 0.852, Tmax = 0.981Rint = 0.027
6399 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106Δρmax = 0.20 e Å−3
S = 1.02Δρmin = −0.21 e Å−3
3571 reflectionsAbsolute structure: Flack (1983), 1511 Friedel pairs
186 parametersAbsolute structure parameter: −0.20 (8)
1 restraint
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
Cl10.97678 (16)1.71550 (10)0.56971 (5)0.0916 (3)
O10.4790 (3)0.9949 (3)0.66410 (13)0.0797 (5)
O20.7288 (3)0.81404 (19)0.79114 (12)0.0616 (4)
O30.4559 (4)0.95006 (19)0.86448 (13)0.0700 (5)
O40.2024 (3)0.2039 (2)0.93940 (13)0.0633 (4)
C10.6002 (4)1.3072 (3)0.60310 (14)0.0559 (5)
H1A0.45081.26360.58150.067*
C20.6676 (5)1.4603 (4)0.57413 (16)0.0634 (6)
H2A0.56501.51960.53310.076*
C30.8875 (5)1.5239 (3)0.60661 (15)0.0579 (6)
C41.0422 (4)1.4387 (3)0.66746 (16)0.0587 (6)
H4A1.19051.48370.68930.070*
C50.9738 (4)1.2856 (3)0.69547 (15)0.0548 (5)
H5A1.07781.22680.73620.066*
C60.7520 (4)1.2176 (3)0.66383 (12)0.0466 (4)
C70.6694 (4)1.0548 (3)0.69417 (15)0.0544 (5)
C80.8296 (4)0.9684 (3)0.76653 (18)0.0609 (6)
H8A0.98790.94960.74510.073*
H8B0.85171.03820.81950.073*
C90.5374 (4)0.8211 (3)0.84121 (15)0.0521 (5)
C100.4532 (4)0.6572 (3)0.86395 (13)0.0458 (5)
C110.2512 (4)0.6426 (3)0.91413 (14)0.0535 (5)
H11A0.17130.73670.93120.064*
C120.1709 (4)0.4916 (3)0.93820 (14)0.0565 (6)
H12A0.03530.48340.97070.068*
C130.2901 (4)0.3505 (3)0.91444 (14)0.0467 (5)
C140.4930 (4)0.3639 (3)0.86646 (15)0.0520 (5)
H14A0.57630.26980.85160.062*
C150.5711 (4)0.5153 (3)0.84087 (15)0.0495 (5)
H15A0.70520.52290.80750.059*
H1O40.289 (6)0.135 (5)0.924 (2)0.083 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1111 (6)0.0700 (4)0.0958 (5)−0.0168 (4)0.0211 (4)0.0258 (4)
O10.0787 (12)0.0704 (12)0.0853 (11)−0.0250 (11)−0.0197 (9)0.0065 (11)
O20.0618 (9)0.0398 (8)0.0840 (10)0.0020 (8)0.0114 (8)0.0072 (9)
O30.0857 (12)0.0393 (9)0.0855 (12)0.0051 (9)0.0107 (10)−0.0103 (9)
O40.0671 (10)0.0527 (10)0.0728 (10)−0.0026 (10)0.0207 (8)0.0070 (9)
C10.0540 (12)0.0605 (15)0.0527 (11)0.0018 (12)0.0012 (9)0.0002 (12)
C20.0657 (14)0.0673 (16)0.0562 (12)0.0059 (13)0.0010 (11)0.0138 (12)
C30.0674 (14)0.0545 (13)0.0546 (11)−0.0056 (12)0.0208 (10)0.0081 (11)
C40.0508 (12)0.0629 (15)0.0633 (13)−0.0090 (12)0.0096 (10)−0.0003 (12)
C50.0509 (11)0.0545 (13)0.0587 (12)−0.0006 (11)0.0032 (9)0.0043 (11)
C60.0480 (10)0.0479 (11)0.0444 (9)0.0032 (10)0.0066 (8)−0.0032 (10)
C70.0560 (12)0.0485 (12)0.0582 (12)−0.0018 (11)0.0018 (10)−0.0061 (11)
C80.0563 (12)0.0468 (13)0.0788 (15)−0.0019 (11)0.0014 (11)0.0101 (12)
C90.0566 (12)0.0415 (12)0.0567 (12)0.0036 (11)−0.0031 (10)−0.0033 (11)
C100.0485 (10)0.0385 (10)0.0499 (11)0.0024 (9)0.0009 (8)−0.0027 (9)
C110.0536 (12)0.0481 (12)0.0595 (12)0.0093 (10)0.0085 (10)−0.0084 (11)
C120.0519 (12)0.0622 (15)0.0568 (12)0.0049 (12)0.0128 (9)−0.0031 (12)
C130.0510 (11)0.0441 (11)0.0451 (10)−0.0010 (10)0.0052 (9)0.0012 (9)
C140.0580 (12)0.0401 (12)0.0594 (12)0.0063 (10)0.0128 (10)−0.0010 (10)
C150.0489 (11)0.0435 (11)0.0569 (11)0.0025 (11)0.0101 (9)−0.0013 (11)
Geometric parameters (Å, º) top
Cl1—C31.738 (3)C5—H5A0.9300
O1—C71.209 (3)C6—C71.483 (3)
O2—C91.349 (3)C7—C81.505 (3)
O2—C81.434 (3)C8—H8A0.9700
O3—C91.204 (3)C8—H8B0.9700
O4—C131.351 (3)C9—C101.461 (3)
O4—H1O40.79 (3)C10—C151.384 (3)
C1—C21.380 (4)C10—C111.402 (3)
C1—C61.383 (3)C11—C121.364 (4)
C1—H1A0.9300C11—H11A0.9300
C2—C31.369 (4)C12—C131.385 (3)
C2—H2A0.9300C12—H12A0.9300
C3—C41.375 (4)C13—C141.386 (3)
C4—C51.376 (3)C14—C151.370 (3)
C4—H4A0.9300C14—H14A0.9300
C5—C61.389 (3)C15—H15A0.9300
C9—O2—C8116.48 (19)C7—C8—H8A109.2
C13—O4—H1O4108 (2)O2—C8—H8B109.2
C2—C1—C6120.9 (2)C7—C8—H8B109.2
C2—C1—H1A119.5H8A—C8—H8B107.9
C6—C1—H1A119.5O3—C9—O2121.8 (2)
C3—C2—C1119.2 (2)O3—C9—C10126.4 (2)
C3—C2—H2A120.4O2—C9—C10111.78 (19)
C1—C2—H2A120.4C15—C10—C11118.4 (2)
C2—C3—C4121.5 (2)C15—C10—C9122.44 (19)
C2—C3—Cl1119.7 (2)C11—C10—C9119.07 (19)
C4—C3—Cl1118.8 (2)C12—C11—C10120.6 (2)
C3—C4—C5118.9 (2)C12—C11—H11A119.7
C3—C4—H4A120.5C10—C11—H11A119.7
C5—C4—H4A120.5C11—C12—C13120.35 (19)
C4—C5—C6121.1 (2)C11—C12—H12A119.8
C4—C5—H5A119.5C13—C12—H12A119.8
C6—C5—H5A119.5O4—C13—C12118.0 (2)
C1—C6—C5118.5 (2)O4—C13—C14122.5 (2)
C1—C6—C7118.9 (2)C12—C13—C14119.5 (2)
C5—C6—C7122.6 (2)C15—C14—C13120.2 (2)
O1—C7—C6122.0 (2)C15—C14—H14A119.9
O1—C7—C8120.9 (2)C13—C14—H14A119.9
C6—C7—C8117.15 (19)C14—C15—C10120.92 (19)
O2—C8—C7111.9 (2)C14—C15—H15A119.5
O2—C8—H8A109.2C10—C15—H15A119.5
C6—C1—C2—C3−0.3 (3)C8—O2—C9—O3−0.4 (3)
C1—C2—C3—C4−0.1 (4)C8—O2—C9—C10−178.72 (19)
C1—C2—C3—Cl1179.18 (18)O3—C9—C10—C15−174.2 (2)
C2—C3—C4—C50.5 (3)O2—C9—C10—C154.1 (3)
Cl1—C3—C4—C5−178.78 (17)O3—C9—C10—C113.2 (3)
C3—C4—C5—C6−0.5 (3)O2—C9—C10—C11−178.51 (18)
C2—C1—C6—C50.3 (3)C15—C10—C11—C12−1.1 (3)
C2—C1—C6—C7178.9 (2)C9—C10—C11—C12−178.6 (2)
C4—C5—C6—C10.1 (3)C10—C11—C12—C130.9 (3)
C4—C5—C6—C7−178.4 (2)C11—C12—C13—O4−179.6 (2)
C1—C6—C7—O13.7 (3)C11—C12—C13—C140.4 (3)
C5—C6—C7—O1−177.8 (2)O4—C13—C14—C15178.4 (2)
C1—C6—C7—C8−174.6 (2)C12—C13—C14—C15−1.6 (3)
C5—C6—C7—C84.0 (3)C13—C14—C15—C101.4 (3)
C9—O2—C8—C7−73.7 (3)C11—C10—C15—C14−0.1 (3)
O1—C7—C8—O20.8 (3)C9—C10—C15—C14177.3 (2)
C6—C7—C8—O2179.02 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1O4···O3i0.78 (4)2.01 (4)2.783 (3)168 (3)
Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formulaC15H11ClO4
Mr290.69
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)5.5307 (10), 8.1324 (15), 14.857 (2)
β (°) 95.120 (4)
V (Å3)665.57 (19)
Z2
Radiation typeMo Kα
µ (mm−1)0.30
Crystal size (mm)0.56 × 0.23 × 0.07
Data collection
DiffractometerBruker APEXII DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.852, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections		6399, 3571, 2457
Rint0.027
(sin θ/λ)max (Å−1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.106, 1.02
No. of reflections3571
No. of parameters186
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.20, −0.21
Absolute structureFlack (1983), 1511 Friedel pairs
Absolute structure parameter−0.20 (8)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SAINT (Bruker, 2009, SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1O4···O3i0.78 (4)2.01 (4)2.783 (3)168 (3)
Symmetry code: (i) x, y−1, z.
 

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship.

References

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Volume 67| Part 10| October 2011| Page o2682
https://doi.org/10.1107/S1600536811037500
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