2-(4-Chloro-phen-yl)-2-oxoethyl 4-hy-droxy-benzoate.

The title compound, C(15)H(11)ClO(4), consists of a chloro-benzene 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 chloro-benzene and phenol rings is 65.70 (11)°. In the crystal, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains along [010].

Related literature

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

Crystal data

C15H11ClO4

M = 290.69

Monoclinic,

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 ▶) T min = 0.852, T max = 0.981

6399 measured reflections

3571 independent reflections

2457 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 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 ▶), 1511 Friedel pairs

Flack parameter: −0.20 (8)

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037500/bq2305sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037500/bq2305Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037500/bq2305Isup3.cml

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

C15H11ClO4	F(000) = 300
Mr = 290.69	Dx = 1.450 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1832 reflections
a = 5.5307 (10) Å	θ = 3.7–24.1°
b = 8.1324 (15) Å	µ = 0.30 mm−1
c = 14.857 (2) Å	T = 296 K
β = 95.120 (4)°	Plate, colourless
V = 665.57 (19) Å3	0.56 × 0.23 × 0.07 mm
Z = 2

Bruker APEXII DUO CCD area-detector diffractometer	3571 independent reflections
Radiation source: fine-focus sealed tube	2457 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 30.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→7
Tmin = 0.852, Tmax = 0.981	k = −11→11
6399 measured reflections	l = −20→20

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)] = 0.044	H 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 reflections	Δρmax = 0.20 e Å−3
186 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: Flack (1983), 1511 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.20 (8)

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
Cl1	0.97678 (16)	1.71550 (10)	0.56971 (5)	0.0916 (3)
O1	0.4790 (3)	0.9949 (3)	0.66410 (13)	0.0797 (5)
O2	0.7288 (3)	0.81404 (19)	0.79114 (12)	0.0616 (4)
O3	0.4559 (4)	0.95006 (19)	0.86448 (13)	0.0700 (5)
O4	0.2024 (3)	0.2039 (2)	0.93940 (13)	0.0633 (4)
C1	0.6002 (4)	1.3072 (3)	0.60310 (14)	0.0559 (5)
H1A	0.4508	1.2636	0.5815	0.067*
C2	0.6676 (5)	1.4603 (4)	0.57413 (16)	0.0634 (6)
H2A	0.5650	1.5196	0.5331	0.076*
C3	0.8875 (5)	1.5239 (3)	0.60661 (15)	0.0579 (6)
C4	1.0422 (4)	1.4387 (3)	0.66746 (16)	0.0587 (6)
H4A	1.1905	1.4837	0.6893	0.070*
C5	0.9738 (4)	1.2856 (3)	0.69547 (15)	0.0548 (5)
H5A	1.0778	1.2268	0.7362	0.066*
C6	0.7520 (4)	1.2176 (3)	0.66383 (12)	0.0466 (4)
C7	0.6694 (4)	1.0548 (3)	0.69417 (15)	0.0544 (5)
C8	0.8296 (4)	0.9684 (3)	0.76653 (18)	0.0609 (6)
H8A	0.9879	0.9496	0.7451	0.073*
H8B	0.8517	1.0382	0.8195	0.073*
C9	0.5374 (4)	0.8211 (3)	0.84121 (15)	0.0521 (5)
C10	0.4532 (4)	0.6572 (3)	0.86395 (13)	0.0458 (5)
C11	0.2512 (4)	0.6426 (3)	0.91413 (14)	0.0535 (5)
H11A	0.1713	0.7367	0.9312	0.064*
C12	0.1709 (4)	0.4916 (3)	0.93820 (14)	0.0565 (6)
H12A	0.0353	0.4834	0.9707	0.068*
C13	0.2901 (4)	0.3505 (3)	0.91444 (14)	0.0467 (5)
C14	0.4930 (4)	0.3639 (3)	0.86646 (15)	0.0520 (5)
H14A	0.5763	0.2698	0.8516	0.062*
C15	0.5711 (4)	0.5153 (3)	0.84087 (15)	0.0495 (5)
H15A	0.7052	0.5229	0.8075	0.059*
H1O4	0.289 (6)	0.135 (5)	0.924 (2)	0.083 (11)*

	U11	U22	U33	U12	U13	U23
Cl1	0.1111 (6)	0.0700 (4)	0.0958 (5)	−0.0168 (4)	0.0211 (4)	0.0258 (4)
O1	0.0787 (12)	0.0704 (12)	0.0853 (11)	−0.0250 (11)	−0.0197 (9)	0.0065 (11)
O2	0.0618 (9)	0.0398 (8)	0.0840 (10)	0.0020 (8)	0.0114 (8)	0.0072 (9)
O3	0.0857 (12)	0.0393 (9)	0.0855 (12)	0.0051 (9)	0.0107 (10)	−0.0103 (9)
O4	0.0671 (10)	0.0527 (10)	0.0728 (10)	−0.0026 (10)	0.0207 (8)	0.0070 (9)
C1	0.0540 (12)	0.0605 (15)	0.0527 (11)	0.0018 (12)	0.0012 (9)	0.0002 (12)
C2	0.0657 (14)	0.0673 (16)	0.0562 (12)	0.0059 (13)	0.0010 (11)	0.0138 (12)
C3	0.0674 (14)	0.0545 (13)	0.0546 (11)	−0.0056 (12)	0.0208 (10)	0.0081 (11)
C4	0.0508 (12)	0.0629 (15)	0.0633 (13)	−0.0090 (12)	0.0096 (10)	−0.0003 (12)
C5	0.0509 (11)	0.0545 (13)	0.0587 (12)	−0.0006 (11)	0.0032 (9)	0.0043 (11)
C6	0.0480 (10)	0.0479 (11)	0.0444 (9)	0.0032 (10)	0.0066 (8)	−0.0032 (10)
C7	0.0560 (12)	0.0485 (12)	0.0582 (12)	−0.0018 (11)	0.0018 (10)	−0.0061 (11)
C8	0.0563 (12)	0.0468 (13)	0.0788 (15)	−0.0019 (11)	0.0014 (11)	0.0101 (12)
C9	0.0566 (12)	0.0415 (12)	0.0567 (12)	0.0036 (11)	−0.0031 (10)	−0.0033 (11)
C10	0.0485 (10)	0.0385 (10)	0.0499 (11)	0.0024 (9)	0.0009 (8)	−0.0027 (9)
C11	0.0536 (12)	0.0481 (12)	0.0595 (12)	0.0093 (10)	0.0085 (10)	−0.0084 (11)
C12	0.0519 (12)	0.0622 (15)	0.0568 (12)	0.0049 (12)	0.0128 (9)	−0.0031 (12)
C13	0.0510 (11)	0.0441 (11)	0.0451 (10)	−0.0010 (10)	0.0052 (9)	0.0012 (9)
C14	0.0580 (12)	0.0401 (12)	0.0594 (12)	0.0063 (10)	0.0128 (10)	−0.0010 (10)
C15	0.0489 (11)	0.0435 (11)	0.0569 (11)	0.0025 (11)	0.0101 (9)	−0.0013 (11)

Cl1—C3	1.738 (3)	C5—H5A	0.9300
O1—C7	1.209 (3)	C6—C7	1.483 (3)
O2—C9	1.349 (3)	C7—C8	1.505 (3)
O2—C8	1.434 (3)	C8—H8A	0.9700
O3—C9	1.204 (3)	C8—H8B	0.9700
O4—C13	1.351 (3)	C9—C10	1.461 (3)
O4—H1O4	0.79 (3)	C10—C15	1.384 (3)
C1—C2	1.380 (4)	C10—C11	1.402 (3)
C1—C6	1.383 (3)	C11—C12	1.364 (4)
C1—H1A	0.9300	C11—H11A	0.9300
C2—C3	1.369 (4)	C12—C13	1.385 (3)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.375 (4)	C13—C14	1.386 (3)
C4—C5	1.376 (3)	C14—C15	1.370 (3)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.389 (3)	C15—H15A	0.9300
C9—O2—C8	116.48 (19)	C7—C8—H8A	109.2
C13—O4—H1O4	108 (2)	O2—C8—H8B	109.2
C2—C1—C6	120.9 (2)	C7—C8—H8B	109.2
C2—C1—H1A	119.5	H8A—C8—H8B	107.9
C6—C1—H1A	119.5	O3—C9—O2	121.8 (2)
C3—C2—C1	119.2 (2)	O3—C9—C10	126.4 (2)
C3—C2—H2A	120.4	O2—C9—C10	111.78 (19)
C1—C2—H2A	120.4	C15—C10—C11	118.4 (2)
C2—C3—C4	121.5 (2)	C15—C10—C9	122.44 (19)
C2—C3—Cl1	119.7 (2)	C11—C10—C9	119.07 (19)
C4—C3—Cl1	118.8 (2)	C12—C11—C10	120.6 (2)
C3—C4—C5	118.9 (2)	C12—C11—H11A	119.7
C3—C4—H4A	120.5	C10—C11—H11A	119.7
C5—C4—H4A	120.5	C11—C12—C13	120.35 (19)
C4—C5—C6	121.1 (2)	C11—C12—H12A	119.8
C4—C5—H5A	119.5	C13—C12—H12A	119.8
C6—C5—H5A	119.5	O4—C13—C12	118.0 (2)
C1—C6—C5	118.5 (2)	O4—C13—C14	122.5 (2)
C1—C6—C7	118.9 (2)	C12—C13—C14	119.5 (2)
C5—C6—C7	122.6 (2)	C15—C14—C13	120.2 (2)
O1—C7—C6	122.0 (2)	C15—C14—H14A	119.9
O1—C7—C8	120.9 (2)	C13—C14—H14A	119.9
C6—C7—C8	117.15 (19)	C14—C15—C10	120.92 (19)
O2—C8—C7	111.9 (2)	C14—C15—H15A	119.5
O2—C8—H8A	109.2	C10—C15—H15A	119.5
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—Cl1	179.18 (18)	O3—C9—C10—C15	−174.2 (2)
C2—C3—C4—C5	0.5 (3)	O2—C9—C10—C15	4.1 (3)
Cl1—C3—C4—C5	−178.78 (17)	O3—C9—C10—C11	3.2 (3)
C3—C4—C5—C6	−0.5 (3)	O2—C9—C10—C11	−178.51 (18)
C2—C1—C6—C5	0.3 (3)	C15—C10—C11—C12	−1.1 (3)
C2—C1—C6—C7	178.9 (2)	C9—C10—C11—C12	−178.6 (2)
C4—C5—C6—C1	0.1 (3)	C10—C11—C12—C13	0.9 (3)
C4—C5—C6—C7	−178.4 (2)	C11—C12—C13—O4	−179.6 (2)
C1—C6—C7—O1	3.7 (3)	C11—C12—C13—C14	0.4 (3)
C5—C6—C7—O1	−177.8 (2)	O4—C13—C14—C15	178.4 (2)
C1—C6—C7—C8	−174.6 (2)	C12—C13—C14—C15	−1.6 (3)
C5—C6—C7—C8	4.0 (3)	C13—C14—C15—C10	1.4 (3)
C9—O2—C8—C7	−73.7 (3)	C11—C10—C15—C14	−0.1 (3)
O1—C7—C8—O2	0.8 (3)	C9—C10—C15—C14	177.3 (2)
C6—C7—C8—O2	179.02 (18)

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)

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) .