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

In the title compound, C(16)H(13)ClO(3), the dihedral angle between the benzene rings is 80.74 (8)°. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules to form C(11) chains propagating in [010].

Related literature

For a related structure and background references to phenacyl benzoates, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C16H13ClO3

M = 288.71

Monoclinic,

a = 5.9132 (4) Å

b = 8.5044 (6) Å

c = 27.8767 (18) Å

β = 95.880 (1)°

V = 1394.49 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 297 K

0.51 × 0.30 × 0.06 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.871, T max = 0.983

21275 measured reflections

4070 independent reflections

2628 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.144

S = 1.05

4070 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.42 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, PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042851/hb6454sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042851/hb6454Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042851/hb6454Isup3.cml

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

C16H13ClO3	F(000) = 600
Mr = 288.71	Dx = 1.375 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4428 reflections
a = 5.9132 (4) Å	θ = 2.8–28.1°
b = 8.5044 (6) Å	µ = 0.28 mm−1
c = 27.8767 (18) Å	T = 297 K
β = 95.880 (1)°	Plate, colourless
V = 1394.49 (16) Å3	0.51 × 0.30 × 0.06 mm
Z = 4

Bruker SMART APEXII DUO CCD diffractometer	4070 independent reflections
Radiation source: fine-focus sealed tube	2628 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 30.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.871, Tmax = 0.983	k = −11→12
21275 measured reflections	l = −39→39

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0587P)2 + 0.3124P] where P = (Fo2 + 2Fc2)/3
4070 reflections	(Δ/σ)max = 0.002
182 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.42 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	1.34410 (11)	0.75388 (9)	1.047675 (19)	0.0935 (2)
O1	0.5306 (2)	0.69016 (17)	0.86404 (5)	0.0739 (4)
O2	0.6246 (2)	0.50027 (17)	0.79276 (4)	0.0612 (3)
O3	0.3791 (2)	0.35541 (15)	0.83027 (4)	0.0643 (3)
C1	0.8059 (3)	0.7539 (2)	0.94970 (7)	0.0569 (4)
H1A	0.6646	0.8027	0.9453	0.068*
C2	0.9496 (4)	0.7851 (2)	0.99053 (7)	0.0646 (5)
H2A	0.9056	0.8539	1.0138	0.078*
C3	1.1586 (3)	0.7138 (2)	0.99658 (6)	0.0589 (4)
C4	1.2267 (3)	0.6099 (2)	0.96302 (6)	0.0598 (4)
H4A	1.3684	0.5617	0.9678	0.072*
C5	1.0808 (3)	0.5784 (2)	0.92215 (6)	0.0530 (4)
H5A	1.1248	0.5083	0.8992	0.064*
C6	0.8693 (3)	0.65035 (18)	0.91501 (5)	0.0462 (3)
C7	0.7093 (3)	0.62133 (19)	0.87099 (6)	0.0487 (4)
C8	0.7785 (3)	0.5032 (2)	0.83558 (6)	0.0579 (4)
H8A	0.9298	0.5283	0.8273	0.070*
H8B	0.7842	0.3997	0.8503	0.070*
C9	0.4256 (3)	0.42441 (19)	0.79494 (6)	0.0484 (4)
C10	0.2774 (3)	0.43770 (17)	0.74889 (5)	0.0438 (3)
C11	0.3350 (3)	0.53418 (19)	0.71169 (6)	0.0496 (4)
H11A	0.4730	0.5876	0.7146	0.060*
C12	0.1863 (3)	0.55014 (19)	0.67042 (6)	0.0523 (4)
H12A	0.2264	0.6144	0.6456	0.063*
C13	−0.0210 (3)	0.47287 (18)	0.66499 (5)	0.0482 (4)
C14	−0.0734 (3)	0.3726 (2)	0.70156 (6)	0.0531 (4)
H14A	−0.2093	0.3166	0.6982	0.064*
C15	0.0749 (3)	0.3551 (2)	0.74308 (6)	0.0505 (4)
H15A	0.0379	0.2873	0.7672	0.061*
C16	−0.1878 (3)	0.5006 (2)	0.62043 (6)	0.0604 (4)
H16A	−0.1102	0.4892	0.5920	0.091*
H16B	−0.2492	0.6049	0.6215	0.091*
H16C	−0.3089	0.4252	0.6197	0.091*

	U11	U22	U33	U12	U13	U23
Cl1	0.0873 (4)	0.1316 (6)	0.0578 (3)	−0.0190 (4)	−0.0114 (3)	−0.0225 (3)
O1	0.0601 (8)	0.0737 (8)	0.0831 (9)	0.0200 (7)	−0.0156 (7)	−0.0148 (7)
O2	0.0487 (6)	0.0890 (9)	0.0452 (6)	−0.0116 (6)	0.0008 (5)	−0.0060 (6)
O3	0.0746 (8)	0.0656 (8)	0.0513 (7)	−0.0104 (7)	−0.0006 (6)	0.0087 (6)
C1	0.0517 (9)	0.0576 (10)	0.0617 (10)	0.0007 (8)	0.0071 (8)	−0.0088 (8)
C2	0.0714 (12)	0.0683 (11)	0.0555 (10)	−0.0103 (10)	0.0130 (9)	−0.0163 (8)
C3	0.0615 (10)	0.0705 (11)	0.0438 (8)	−0.0165 (9)	0.0011 (7)	−0.0034 (8)
C4	0.0510 (9)	0.0736 (11)	0.0526 (9)	0.0014 (8)	−0.0044 (7)	−0.0015 (8)
C5	0.0518 (9)	0.0582 (9)	0.0480 (8)	0.0033 (7)	0.0011 (7)	−0.0065 (7)
C6	0.0466 (8)	0.0462 (8)	0.0457 (8)	−0.0043 (6)	0.0039 (6)	−0.0001 (6)
C7	0.0452 (8)	0.0482 (8)	0.0518 (8)	−0.0021 (7)	−0.0002 (7)	0.0017 (7)
C8	0.0470 (9)	0.0747 (11)	0.0503 (9)	0.0005 (8)	−0.0042 (7)	−0.0102 (8)
C9	0.0497 (8)	0.0485 (8)	0.0469 (8)	0.0006 (7)	0.0046 (7)	−0.0075 (7)
C10	0.0455 (8)	0.0443 (7)	0.0418 (7)	−0.0007 (6)	0.0059 (6)	−0.0054 (6)
C11	0.0483 (8)	0.0488 (8)	0.0522 (8)	−0.0082 (7)	0.0071 (7)	0.0001 (7)
C12	0.0617 (10)	0.0492 (8)	0.0467 (8)	−0.0037 (7)	0.0081 (7)	0.0046 (7)
C13	0.0532 (9)	0.0478 (8)	0.0431 (8)	0.0039 (7)	0.0030 (6)	−0.0083 (6)
C14	0.0483 (8)	0.0598 (10)	0.0508 (8)	−0.0109 (7)	0.0040 (7)	−0.0052 (7)
C15	0.0518 (9)	0.0555 (9)	0.0449 (8)	−0.0097 (7)	0.0082 (7)	0.0004 (7)
C16	0.0638 (11)	0.0631 (10)	0.0524 (9)	0.0048 (9)	−0.0030 (8)	−0.0047 (8)

Cl1—C3	1.7400 (17)	C8—H8A	0.9700
O1—C7	1.2062 (19)	C8—H8B	0.9700
O2—C9	1.349 (2)	C9—C10	1.483 (2)
O2—C8	1.4250 (18)	C10—C15	1.383 (2)
O3—C9	1.203 (2)	C10—C11	1.392 (2)
C1—C2	1.375 (2)	C11—C12	1.381 (2)
C1—C6	1.387 (2)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.385 (2)
C2—C3	1.371 (3)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.388 (2)
C3—C4	1.377 (3)	C13—C16	1.523 (2)
C4—C5	1.383 (2)	C14—C15	1.387 (2)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.388 (2)	C15—H15A	0.9300
C5—H5A	0.9300	C16—H16A	0.9600
C6—C7	1.491 (2)	C16—H16B	0.9600
C7—C8	1.495 (2)	C16—H16C	0.9600
C9—O2—C8	117.12 (13)	O3—C9—O2	122.98 (15)
C2—C1—C6	120.75 (17)	O3—C9—C10	125.56 (15)
C2—C1—H1A	119.6	O2—C9—C10	111.46 (14)
C6—C1—H1A	119.6	C15—C10—C11	119.15 (14)
C3—C2—C1	119.28 (17)	C15—C10—C9	119.38 (14)
C3—C2—H2A	120.4	C11—C10—C9	121.45 (14)
C1—C2—H2A	120.4	C12—C11—C10	119.66 (15)
C2—C3—C4	121.52 (16)	C12—C11—H11A	120.2
C2—C3—Cl1	119.91 (15)	C10—C11—H11A	120.2
C4—C3—Cl1	118.57 (15)	C11—C12—C13	121.67 (15)
C3—C4—C5	118.90 (17)	C11—C12—H12A	119.2
C3—C4—H4A	120.5	C13—C12—H12A	119.2
C5—C4—H4A	120.5	C12—C13—C14	118.22 (14)
C4—C5—C6	120.60 (16)	C12—C13—C16	120.48 (15)
C4—C5—H5A	119.7	C14—C13—C16	121.28 (15)
C6—C5—H5A	119.7	C15—C14—C13	120.59 (15)
C1—C6—C5	118.94 (15)	C15—C14—H14A	119.7
C1—C6—C7	118.97 (15)	C13—C14—H14A	119.7
C5—C6—C7	122.08 (14)	C10—C15—C14	120.61 (15)
O1—C7—C6	121.57 (15)	C10—C15—H15A	119.7
O1—C7—C8	120.98 (15)	C14—C15—H15A	119.7
C6—C7—C8	117.46 (13)	C13—C16—H16A	109.5
O2—C8—C7	111.72 (14)	C13—C16—H16B	109.5
O2—C8—H8A	109.3	H16A—C16—H16B	109.5
C7—C8—H8A	109.3	C13—C16—H16C	109.5
O2—C8—H8B	109.3	H16A—C16—H16C	109.5
C7—C8—H8B	109.3	H16B—C16—H16C	109.5
H8A—C8—H8B	107.9
C6—C1—C2—C3	0.6 (3)	C8—O2—C9—O3	−3.1 (2)
C1—C2—C3—C4	−0.9 (3)	C8—O2—C9—C10	176.99 (14)
C1—C2—C3—Cl1	179.20 (14)	O3—C9—C10—C15	−5.7 (2)
C2—C3—C4—C5	0.6 (3)	O2—C9—C10—C15	174.20 (14)
Cl1—C3—C4—C5	−179.55 (14)	O3—C9—C10—C11	172.90 (16)
C3—C4—C5—C6	0.1 (3)	O2—C9—C10—C11	−7.2 (2)
C2—C1—C6—C5	0.0 (3)	C15—C10—C11—C12	2.2 (2)
C2—C1—C6—C7	−179.28 (16)	C9—C10—C11—C12	−176.38 (15)
C4—C5—C6—C1	−0.4 (3)	C10—C11—C12—C13	0.3 (3)
C4—C5—C6—C7	178.91 (16)	C11—C12—C13—C14	−2.6 (2)
C1—C6—C7—O1	2.9 (3)	C11—C12—C13—C16	176.20 (15)
C5—C6—C7—O1	−176.38 (18)	C12—C13—C14—C15	2.3 (2)
C1—C6—C7—C8	−177.07 (16)	C16—C13—C14—C15	−176.49 (15)
C5—C6—C7—C8	3.6 (2)	C11—C10—C15—C14	−2.5 (2)
C9—O2—C8—C7	−77.7 (2)	C9—C10—C15—C14	176.13 (15)
O1—C7—C8—O2	7.0 (3)	C13—C14—C15—C10	0.2 (3)
C6—C7—C8—O2	−173.03 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16C···O1i	0.96	2.46	3.383 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16C⋯O1i	0.96	2.46	3.383 (2)	162

Symmetry code: (i) .