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

The title compound, C(16)H(13)BrO(3), consists of a toluene ring and a bromo-benzene ring which are linked together by a 2-oxopropyl acetate group. The dihedral angle formed between the toluene and bromo-benzene rings is 80.70 (7)°. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For applications of phenacyl benzoate derivatives, see: Rather & Reid (1919 ▶); Judefind & Reid (1920 ▶); Gandhi et al. (1995 ▶); Huang et al. (1996 ▶); Sheehan & Umezaw (1973 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶). For a related structure, see: Fun et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H13BrO3

M = 333.17

Monoclinic,

a = 5.8368 (2) Å

b = 8.3438 (3) Å

c = 27.9684 (8) Å

β = 95.177 (1)°

V = 1356.54 (8) Å3

Z = 4

Mo Kα radiation

μ = 3.03 mm−1

T = 100 K

0.50 × 0.14 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.311, T max = 0.707

14735 measured reflections

3936 independent reflections

3395 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.074

S = 1.02

3936 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.45 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045272/hg5125sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045272/hg5125Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045272/hg5125Isup3.cml

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

C16H13BrO3	F(000) = 672
Mr = 333.17	Dx = 1.631 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6134 reflections
a = 5.8368 (2) Å	θ = 2.6–32.4°
b = 8.3438 (3) Å	µ = 3.03 mm−1
c = 27.9684 (8) Å	T = 100 K
β = 95.177 (1)°	Needle, yellow
V = 1356.54 (8) Å3	0.50 × 0.14 × 0.12 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3936 independent reflections
Radiation source: fine-focus sealed tube	3395 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.311, Tmax = 0.707	k = −11→11
14735 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0324P)2 + 1.2242P] where P = (Fo2 + 2Fc2)/3
3936 reflections	(Δ/σ)max = 0.002
182 parameters	Δρmax = 0.45 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
Br1	1.36051 (3)	0.73030 (2)	1.049704 (6)	0.02370 (7)
O1	0.6371 (2)	1.02498 (16)	0.79328 (4)	0.0188 (3)
O2	0.5266 (2)	0.82885 (16)	0.86329 (5)	0.0228 (3)
O3	0.3804 (2)	1.16704 (15)	0.83172 (4)	0.0193 (3)
C1	1.0857 (3)	0.9333 (2)	0.92209 (6)	0.0166 (3)
H1A	1.1334	1.0088	0.8996	0.020*
C2	1.2317 (3)	0.8944 (2)	0.96256 (6)	0.0177 (3)
H2A	1.3795	0.9423	0.9677	0.021*
C3	1.1589 (3)	0.7853 (2)	0.99509 (6)	0.0171 (3)
C4	0.9420 (3)	0.7134 (2)	0.98883 (6)	0.0184 (3)
H4A	0.8935	0.6401	1.0119	0.022*
C5	0.7995 (3)	0.7520 (2)	0.94806 (7)	0.0179 (3)
H5A	0.6523	0.7032	0.9429	0.022*
C6	0.8693 (3)	0.86164 (19)	0.91454 (6)	0.0154 (3)
C7	0.7111 (3)	0.8959 (2)	0.87074 (6)	0.0161 (3)
C8	0.7881 (3)	1.0191 (2)	0.83609 (6)	0.0177 (3)
H8A	0.7936	1.1258	0.8516	0.021*
H8B	0.9453	0.9925	0.8279	0.021*
C9	0.4324 (3)	1.09906 (19)	0.79604 (6)	0.0150 (3)
C10	0.2867 (3)	1.08669 (19)	0.74980 (6)	0.0146 (3)
C11	0.0783 (3)	1.1700 (2)	0.74432 (6)	0.0161 (3)
H11A	0.0369	1.2395	0.7690	0.019*
C12	−0.0687 (3)	1.1510 (2)	0.70261 (6)	0.0173 (3)
H12A	−0.2101	1.2081	0.6991	0.021*
C13	−0.0108 (3)	1.0493 (2)	0.66597 (6)	0.0155 (3)
C14	0.2036 (3)	0.9726 (2)	0.67110 (6)	0.0168 (3)
H14A	0.2490	0.9076	0.6457	0.020*
C15	0.3505 (3)	0.9897 (2)	0.71243 (6)	0.0166 (3)
H15A	0.4943	0.9357	0.7154	0.020*
C16	−0.1776 (3)	1.0169 (2)	0.62159 (6)	0.0178 (3)
H16A	−0.2907	1.1038	0.6176	0.027*
H16B	−0.2572	0.9150	0.6256	0.027*
H16C	−0.0917	1.0111	0.5931	0.027*

	U11	U22	U33	U12	U13	U23
Br1	0.02204 (10)	0.03193 (11)	0.01642 (9)	0.00268 (7)	−0.00216 (6)	0.00657 (7)
O1	0.0149 (6)	0.0279 (6)	0.0133 (6)	0.0042 (5)	−0.0009 (5)	0.0007 (5)
O2	0.0189 (6)	0.0216 (6)	0.0267 (7)	−0.0048 (5)	−0.0049 (5)	0.0034 (5)
O3	0.0223 (6)	0.0201 (6)	0.0151 (6)	0.0030 (5)	0.0003 (5)	−0.0024 (5)
C1	0.0174 (8)	0.0179 (7)	0.0143 (8)	−0.0008 (6)	0.0001 (6)	0.0017 (6)
C2	0.0166 (8)	0.0202 (8)	0.0159 (8)	−0.0012 (6)	0.0000 (6)	−0.0002 (6)
C3	0.0179 (8)	0.0201 (8)	0.0130 (7)	0.0040 (6)	0.0006 (6)	0.0005 (6)
C4	0.0183 (8)	0.0190 (8)	0.0183 (8)	0.0017 (6)	0.0045 (6)	0.0039 (6)
C5	0.0153 (8)	0.0177 (8)	0.0207 (8)	0.0006 (6)	0.0014 (6)	0.0017 (6)
C6	0.0168 (8)	0.0142 (7)	0.0148 (7)	0.0009 (6)	−0.0003 (6)	−0.0008 (6)
C7	0.0166 (8)	0.0152 (7)	0.0160 (8)	0.0020 (6)	−0.0005 (6)	−0.0011 (6)
C8	0.0155 (8)	0.0220 (8)	0.0150 (8)	−0.0003 (6)	−0.0025 (6)	0.0022 (6)
C9	0.0157 (7)	0.0138 (7)	0.0154 (8)	−0.0005 (6)	0.0007 (6)	0.0022 (6)
C10	0.0154 (7)	0.0146 (7)	0.0136 (7)	−0.0004 (6)	0.0012 (6)	0.0011 (6)
C11	0.0168 (8)	0.0177 (7)	0.0139 (7)	0.0011 (6)	0.0014 (6)	−0.0003 (6)
C12	0.0153 (8)	0.0188 (8)	0.0176 (8)	0.0031 (6)	0.0006 (6)	0.0023 (6)
C13	0.0167 (8)	0.0164 (7)	0.0134 (7)	−0.0033 (6)	0.0020 (6)	0.0036 (6)
C14	0.0204 (8)	0.0154 (7)	0.0151 (8)	−0.0001 (6)	0.0036 (6)	−0.0018 (6)
C15	0.0162 (8)	0.0163 (7)	0.0175 (8)	0.0018 (6)	0.0016 (6)	0.0005 (6)
C16	0.0164 (8)	0.0174 (7)	0.0198 (8)	0.0002 (6)	0.0018 (6)	0.0033 (6)

Br1—C3	1.8986 (16)	C8—H8A	0.9900
O1—C9	1.354 (2)	C8—H8B	0.9900
O1—C8	1.4222 (19)	C9—C10	1.486 (2)
O2—C7	1.215 (2)	C10—C11	1.397 (2)
O3—C9	1.210 (2)	C10—C15	1.399 (2)
C1—C2	1.393 (2)	C11—C12	1.394 (2)
C1—C6	1.396 (2)	C11—H11A	0.9500
C1—H1A	0.9500	C12—C13	1.395 (2)
C2—C3	1.381 (2)	C12—H12A	0.9500
C2—H2A	0.9500	C13—C14	1.402 (2)
C3—C4	1.397 (3)	C13—C16	1.531 (2)
C4—C5	1.387 (2)	C14—C15	1.383 (2)
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.397 (2)	C15—H15A	0.9500
C5—H5A	0.9500	C16—H16A	0.9800
C6—C7	1.494 (2)	C16—H16B	0.9800
C7—C8	1.509 (2)	C16—H16C	0.9800
C9—O1—C8	116.81 (14)	O3—C9—O1	123.32 (15)
C2—C1—C6	120.12 (16)	O3—C9—C10	125.74 (16)
C2—C1—H1A	119.9	O1—C9—C10	110.94 (14)
C6—C1—H1A	119.9	C11—C10—C15	119.59 (15)
C3—C2—C1	119.15 (16)	C11—C10—C9	119.01 (15)
C3—C2—H2A	120.4	C15—C10—C9	121.37 (15)
C1—C2—H2A	120.4	C12—C11—C10	119.97 (16)
C2—C3—C4	121.99 (16)	C12—C11—H11A	120.0
C2—C3—Br1	118.94 (13)	C10—C11—H11A	120.0
C4—C3—Br1	119.08 (13)	C11—C12—C13	120.80 (16)
C5—C4—C3	118.20 (16)	C11—C12—H12A	119.6
C5—C4—H4A	120.9	C13—C12—H12A	119.6
C3—C4—H4A	120.9	C12—C13—C14	118.42 (15)
C4—C5—C6	120.94 (16)	C12—C13—C16	121.62 (15)
C4—C5—H5A	119.5	C14—C13—C16	119.94 (15)
C6—C5—H5A	119.5	C15—C14—C13	121.25 (16)
C1—C6—C5	119.59 (15)	C15—C14—H14A	119.4
C1—C6—C7	121.73 (15)	C13—C14—H14A	119.4
C5—C6—C7	118.66 (15)	C14—C15—C10	119.84 (16)
O2—C7—C6	121.70 (16)	C14—C15—H15A	120.1
O2—C7—C8	120.97 (15)	C10—C15—H15A	120.1
C6—C7—C8	117.33 (14)	C13—C16—H16A	109.5
O1—C8—C7	111.48 (14)	C13—C16—H16B	109.5
O1—C8—H8A	109.3	H16A—C16—H16B	109.5
C7—C8—H8A	109.3	C13—C16—H16C	109.5
O1—C8—H8B	109.3	H16A—C16—H16C	109.5
C7—C8—H8B	109.3	H16B—C16—H16C	109.5
H8A—C8—H8B	108.0
C6—C1—C2—C3	−0.5 (3)	C8—O1—C9—O3	4.6 (2)
C1—C2—C3—C4	−0.5 (3)	C8—O1—C9—C10	−176.21 (14)
C1—C2—C3—Br1	179.08 (13)	O3—C9—C10—C11	5.6 (3)
C2—C3—C4—C5	1.2 (3)	O1—C9—C10—C11	−173.61 (15)
Br1—C3—C4—C5	−178.36 (13)	O3—C9—C10—C15	−172.35 (17)
C3—C4—C5—C6	−1.0 (3)	O1—C9—C10—C15	8.5 (2)
C2—C1—C6—C5	0.7 (3)	C15—C10—C11—C12	2.6 (3)
C2—C1—C6—C7	−177.82 (16)	C9—C10—C11—C12	−175.38 (16)
C4—C5—C6—C1	0.1 (3)	C10—C11—C12—C13	0.1 (3)
C4—C5—C6—C7	178.61 (16)	C11—C12—C13—C14	−3.0 (3)
C1—C6—C7—O2	177.11 (17)	C11—C12—C13—C16	175.28 (16)
C5—C6—C7—O2	−1.4 (3)	C12—C13—C14—C15	3.4 (3)
C1—C6—C7—C8	−3.6 (2)	C16—C13—C14—C15	−174.92 (16)
C5—C6—C7—C8	177.94 (16)	C13—C14—C15—C10	−0.8 (3)
C9—O1—C8—C7	75.60 (19)	C11—C10—C15—C14	−2.2 (3)
O2—C7—C8—O1	−8.3 (2)	C9—C10—C15—C14	175.70 (16)
C6—C7—C8—O1	172.36 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2i	0.98	2.42	3.355 (2)	160.
C16—H16B···O3ii	0.98	2.53	3.451 (2)	157.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2i	0.98	2.42	3.355 (2)	160
C16—H16B⋯O3ii	0.98	2.53	3.451 (2)	157

Symmetry codes: (i) ; (ii) .