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

In the title compound, C(15)H(11)ClO(3), the dihedral angle between the aromatic rings is 84.29 (8)°. In the crystal, mol-ecules are linked by weak C-H⋯π inter-actions.

Related literature

For applications of phenacyl benzoate derivatives, see: Rather & Reid (1919 ▶); Litera et al. (2006 ▶); Huang et al. (1996 ▶); Gandhi et al. (1995 ▶). For related structures, see: Ogata et al. (1987 ▶); Wan et al. (2006 ▶); Zhang et al. (2006 ▶). For reported melting-point details, see: Le et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H11ClO3

M = 274.69

Monoclinic,

a = 8.1955 (9) Å

b = 10.8717 (12) Å

c = 16.5420 (15) Å

β = 117.816 (4)°

V = 1303.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.34 × 0.19 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.908, T max = 0.948

11201 measured reflections

4052 independent reflections

2720 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.126

S = 1.03

4052 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.49 e Å−3

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/S160053681102383X/hb5918sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102383X/hb5918Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102383X/hb5918Isup3.cml

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

C15H11ClO3	F(000) = 568
Mr = 274.69	Dx = 1.400 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2797 reflections
a = 8.1955 (9) Å	θ = 2.3–27.1°
b = 10.8717 (12) Å	µ = 0.29 mm−1
c = 16.5420 (15) Å	T = 296 K
β = 117.816 (4)°	Block, colourless
V = 1303.6 (2) Å3	0.34 × 0.19 × 0.19 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4052 independent reflections
Radiation source: fine-focus sealed tube	2720 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 30.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.908, Tmax = 0.948	k = −15→15
11201 measured reflections	l = −20→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.2649P] where P = (Fo2 + 2Fc2)/3
4052 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

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	0.98407 (8)	1.29129 (4)	1.01748 (4)	0.07410 (18)
O1	0.41826 (16)	0.81706 (12)	0.81726 (7)	0.0648 (3)
O2	0.41542 (15)	0.64299 (10)	0.93059 (7)	0.0544 (3)
O3	0.59892 (16)	0.55553 (13)	0.87990 (9)	0.0722 (4)
C1	0.6218 (2)	1.03708 (15)	0.86536 (10)	0.0509 (3)
H1A	0.5394	1.0250	0.8040	0.061*
C2	0.7272 (2)	1.14249 (14)	0.89170 (12)	0.0545 (4)
H2A	0.7170	1.2011	0.8486	0.065*
C3	0.8484 (2)	1.15975 (14)	0.98327 (11)	0.0507 (3)
C4	0.8651 (2)	1.07434 (15)	1.04787 (11)	0.0555 (4)
H4A	0.9469	1.0874	1.1092	0.067*
C5	0.7593 (2)	0.96902 (14)	1.02070 (10)	0.0505 (3)
H5A	0.7701	0.9109	1.0642	0.061*
C6	0.63658 (18)	0.94852 (13)	0.92902 (9)	0.0435 (3)
C7	0.52322 (18)	0.83503 (14)	0.89703 (10)	0.0458 (3)
C8	0.5435 (2)	0.74141 (15)	0.96859 (10)	0.0524 (4)
H8A	0.6680	0.7087	0.9967	0.063*
H8B	0.5243	0.7814	1.0159	0.063*
C9	0.4586 (2)	0.55549 (15)	0.88590 (10)	0.0510 (3)
C10	0.3128 (2)	0.46016 (14)	0.84710 (9)	0.0473 (3)
C11	0.1476 (2)	0.47129 (15)	0.85064 (10)	0.0520 (3)
H11A	0.1261	0.5397	0.8781	0.062*
C12	0.0150 (2)	0.38051 (17)	0.81327 (11)	0.0622 (4)
H12A	−0.0966	0.3888	0.8147	0.075*
C13	0.0468 (3)	0.27865 (18)	0.77419 (12)	0.0688 (5)
H13A	−0.0424	0.2174	0.7498	0.083*
C14	0.2104 (3)	0.26665 (17)	0.77089 (12)	0.0706 (5)
H14A	0.2317	0.1970	0.7445	0.085*
C15	0.3436 (3)	0.35746 (15)	0.80651 (11)	0.0587 (4)
H15A	0.4534	0.3496	0.8032	0.070*

	U11	U22	U33	U12	U13	U23
Cl1	0.0961 (4)	0.0549 (3)	0.0902 (4)	−0.0203 (2)	0.0593 (3)	−0.0167 (2)
O1	0.0575 (7)	0.0764 (8)	0.0440 (6)	−0.0114 (6)	0.0100 (5)	0.0018 (5)
O2	0.0573 (6)	0.0533 (6)	0.0590 (6)	−0.0116 (5)	0.0325 (5)	−0.0065 (5)
O3	0.0551 (7)	0.0808 (9)	0.0885 (9)	−0.0061 (6)	0.0399 (7)	−0.0124 (7)
C1	0.0525 (8)	0.0567 (9)	0.0423 (7)	0.0060 (7)	0.0212 (6)	0.0066 (6)
C2	0.0646 (9)	0.0483 (8)	0.0593 (9)	0.0064 (7)	0.0361 (8)	0.0109 (7)
C3	0.0559 (8)	0.0453 (7)	0.0615 (9)	−0.0017 (6)	0.0362 (7)	−0.0066 (7)
C4	0.0624 (9)	0.0564 (9)	0.0471 (8)	−0.0057 (7)	0.0251 (7)	−0.0062 (7)
C5	0.0583 (8)	0.0518 (8)	0.0404 (7)	−0.0027 (7)	0.0222 (6)	0.0035 (6)
C6	0.0434 (7)	0.0475 (7)	0.0411 (7)	0.0036 (6)	0.0210 (6)	0.0020 (6)
C7	0.0404 (7)	0.0535 (8)	0.0419 (7)	0.0010 (6)	0.0179 (6)	0.0008 (6)
C8	0.0554 (8)	0.0541 (8)	0.0462 (8)	−0.0102 (7)	0.0224 (7)	−0.0010 (7)
C9	0.0506 (8)	0.0537 (8)	0.0485 (8)	0.0010 (7)	0.0229 (7)	0.0053 (7)
C10	0.0526 (8)	0.0463 (7)	0.0405 (7)	0.0016 (6)	0.0196 (6)	0.0066 (6)
C11	0.0545 (8)	0.0520 (8)	0.0486 (8)	−0.0029 (7)	0.0233 (7)	0.0030 (7)
C12	0.0579 (9)	0.0679 (10)	0.0539 (9)	−0.0110 (8)	0.0203 (8)	0.0042 (8)
C13	0.0739 (12)	0.0609 (10)	0.0541 (10)	−0.0154 (9)	0.0151 (9)	0.0009 (8)
C14	0.0960 (14)	0.0496 (9)	0.0526 (10)	0.0016 (9)	0.0233 (10)	−0.0037 (8)
C15	0.0692 (10)	0.0547 (9)	0.0520 (9)	0.0092 (8)	0.0282 (8)	0.0051 (7)

Cl1—C3	1.7362 (16)	C7—C8	1.510 (2)
O1—C7	1.2083 (17)	C8—H8A	0.9700
O2—C9	1.3492 (19)	C8—H8B	0.9700
O2—C8	1.4235 (18)	C9—C10	1.482 (2)
O3—C9	1.1996 (18)	C10—C15	1.385 (2)
C1—C2	1.378 (2)	C10—C11	1.388 (2)
C1—C6	1.390 (2)	C11—C12	1.382 (2)
C1—H1A	0.9300	C11—H11A	0.9300
C2—C3	1.383 (2)	C12—C13	1.367 (3)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.373 (2)	C13—C14	1.373 (3)
C4—C5	1.379 (2)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.384 (3)
C5—C6	1.3920 (19)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.486 (2)
C9—O2—C8	116.36 (12)	O2—C8—H8B	109.3
C2—C1—C6	121.10 (14)	C7—C8—H8B	109.3
C2—C1—H1A	119.5	H8A—C8—H8B	107.9
C6—C1—H1A	119.5	O3—C9—O2	123.48 (15)
C1—C2—C3	118.90 (14)	O3—C9—C10	125.06 (15)
C1—C2—H2A	120.6	O2—C9—C10	111.46 (13)
C3—C2—H2A	120.6	C15—C10—C11	119.52 (15)
C4—C3—C2	121.36 (15)	C15—C10—C9	118.75 (14)
C4—C3—Cl1	119.15 (13)	C11—C10—C9	121.72 (14)
C2—C3—Cl1	119.49 (13)	C12—C11—C10	119.86 (16)
C3—C4—C5	119.25 (15)	C12—C11—H11A	120.1
C3—C4—H4A	120.4	C10—C11—H11A	120.1
C5—C4—H4A	120.4	C13—C12—C11	120.41 (18)
C4—C5—C6	120.85 (14)	C13—C12—H12A	119.8
C4—C5—H5A	119.6	C11—C12—H12A	119.8
C6—C5—H5A	119.6	C12—C13—C14	120.06 (17)
C1—C6—C5	118.54 (14)	C12—C13—H13A	120.0
C1—C6—C7	119.12 (13)	C14—C13—H13A	120.0
C5—C6—C7	122.34 (13)	C13—C14—C15	120.43 (17)
O1—C7—C6	122.11 (14)	C13—C14—H14A	119.8
O1—C7—C8	120.59 (14)	C15—C14—H14A	119.8
C6—C7—C8	117.30 (12)	C14—C15—C10	119.69 (17)
O2—C8—C7	111.81 (12)	C14—C15—H15A	120.2
O2—C8—H8A	109.3	C10—C15—H15A	120.2
C7—C8—H8A	109.3
C6—C1—C2—C3	−0.4 (2)	C6—C7—C8—O2	174.36 (12)
C1—C2—C3—C4	−0.1 (2)	C8—O2—C9—O3	2.5 (2)
C1—C2—C3—Cl1	179.31 (11)	C8—O2—C9—C10	−178.30 (12)
C2—C3—C4—C5	0.3 (2)	O3—C9—C10—C15	5.2 (2)
Cl1—C3—C4—C5	−179.14 (12)	O2—C9—C10—C15	−173.94 (13)
C3—C4—C5—C6	0.0 (2)	O3—C9—C10—C11	−174.87 (16)
C2—C1—C6—C5	0.7 (2)	O2—C9—C10—C11	5.9 (2)
C2—C1—C6—C7	−178.58 (13)	C15—C10—C11—C12	−0.4 (2)
C4—C5—C6—C1	−0.5 (2)	C9—C10—C11—C12	179.72 (14)
C4—C5—C6—C7	178.73 (14)	C10—C11—C12—C13	1.1 (2)
C1—C6—C7—O1	0.0 (2)	C11—C12—C13—C14	−0.8 (3)
C5—C6—C7—O1	−179.21 (15)	C12—C13—C14—C15	−0.3 (3)
C1—C6—C7—C8	−179.92 (13)	C13—C14—C15—C10	1.1 (3)
C5—C6—C7—C8	0.9 (2)	C11—C10—C15—C14	−0.7 (2)
C9—O2—C8—C7	79.04 (17)	C9—C10—C15—C14	179.19 (15)
O1—C7—C8—O2	−5.6 (2)

Cg2 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Cg2i	0.97	2.96	3.4952 (17)	116

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Cg2i	0.97	2.96	3.4952 (17)	116

Symmetry code: (i) .