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

In the title compound, C(15)H(11)BrO(4), the dihedral angle between the aromatic rings is 66.77 (8)°. In the crystal, O-H⋯O, C-H⋯Br and C-H⋯O hydrogen bonds link the mol-ecules, forming layers lying parallel to (101). The crystal packing is further consolidated by C-H⋯π inter-actions and π-π stacking inter-actions [centroid-centroid distance = 3.5476 (7) Å].

Related literature

For a related structure and background references to phenacyl benzoates, see: Fun et al. (2011 ▶). For the synthesis, see: Lund & Langvad (1932 ▶). For a related structure, see: Jin et al. (2008 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H11BrO4

M = 335.15

Monoclinic,

a = 6.2917 (2) Å

b = 7.7893 (2) Å

c = 26.7497 (8) Å

β = 98.234 (2)°

V = 1297.43 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.18 mm−1

T = 100 K

0.56 × 0.27 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.267, T max = 0.535

15470 measured reflections

4700 independent reflections

3640 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.086

S = 1.04

4700 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.74 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/S1600536811040311/hb6429sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040311/hb6429Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040311/hb6429Isup3.cml

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

C15H11BrO4	F(000) = 672
Mr = 335.15	Dx = 1.716 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6519 reflections
a = 6.2917 (2) Å	θ = 2.7–32.6°
b = 7.7893 (2) Å	µ = 3.18 mm−1
c = 26.7497 (8) Å	T = 100 K
β = 98.234 (2)°	Block, colourless
V = 1297.43 (7) Å3	0.56 × 0.27 × 0.23 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4700 independent reflections
Radiation source: fine-focus sealed tube	3640 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 32.7°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.267, Tmax = 0.535	k = −10→11
15470 measured reflections	l = −40→27

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0359P)2 + 1.236P] where P = (Fo2 + 2Fc2)/3
4700 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	−0.39495 (3)	0.75343 (3)	−0.055105 (7)	0.02365 (6)
O1	0.4302 (2)	0.54838 (19)	0.21200 (5)	0.0227 (3)
O2	0.4827 (2)	0.73017 (18)	0.12916 (5)	0.0238 (3)
O3	0.6284 (2)	0.37103 (19)	0.17068 (5)	0.0247 (3)
O4	1.2215 (2)	0.48897 (18)	0.38337 (5)	0.0226 (3)
H1O4	1.3125	0.4144	0.3802	0.034*
C1	0.1846 (3)	0.7654 (2)	0.04036 (7)	0.0188 (3)
H1A	0.3228	0.8146	0.0404	0.023*
C2	0.0288 (3)	0.7873 (2)	−0.00125 (7)	0.0200 (3)
H2A	0.0596	0.8489	−0.0300	0.024*
C3	−0.1742 (3)	0.7171 (2)	−0.00004 (7)	0.0179 (3)
C4	−0.2212 (3)	0.6222 (2)	0.04075 (7)	0.0196 (3)
H4A	−0.3600	0.5740	0.0406	0.024*
C5	−0.0626 (3)	0.5984 (2)	0.08189 (7)	0.0193 (3)
H5A	−0.0923	0.5322	0.1099	0.023*
C6	0.1407 (3)	0.6715 (2)	0.08233 (7)	0.0173 (3)
C7	0.3110 (3)	0.6554 (2)	0.12660 (7)	0.0180 (3)
C8	0.2639 (3)	0.5418 (3)	0.16963 (7)	0.0221 (4)
H8A	0.1268	0.5784	0.1804	0.027*
H8B	0.2464	0.4218	0.1575	0.027*
C9	0.6069 (3)	0.4528 (2)	0.20814 (7)	0.0192 (3)
C10	0.7646 (3)	0.4610 (2)	0.25472 (6)	0.0172 (3)
C11	0.7237 (3)	0.5494 (2)	0.29804 (7)	0.0192 (3)
H11A	0.5895	0.6051	0.2984	0.023*
C12	0.8786 (3)	0.5556 (2)	0.34023 (7)	0.0205 (3)
H12A	0.8503	0.6154	0.3695	0.025*
C13	1.0759 (3)	0.4745 (2)	0.34009 (7)	0.0194 (3)
C14	1.1169 (3)	0.3844 (2)	0.29743 (7)	0.0203 (3)
H14A	1.2508	0.3283	0.2972	0.024*
C15	0.9606 (3)	0.3775 (2)	0.25526 (7)	0.0188 (3)
H15A	0.9877	0.3148	0.2264	0.023*

	U11	U22	U33	U12	U13	U23
Br1	0.02023 (9)	0.03119 (11)	0.01835 (9)	−0.00343 (7)	−0.00127 (6)	0.00545 (8)
O1	0.0199 (6)	0.0322 (8)	0.0155 (6)	0.0060 (5)	0.0008 (5)	0.0007 (5)
O2	0.0200 (6)	0.0264 (7)	0.0237 (6)	−0.0039 (5)	−0.0012 (5)	−0.0001 (5)
O3	0.0268 (6)	0.0281 (7)	0.0179 (6)	0.0050 (6)	−0.0012 (5)	−0.0049 (5)
O4	0.0223 (6)	0.0244 (7)	0.0192 (6)	0.0043 (5)	−0.0032 (5)	0.0036 (5)
C1	0.0184 (7)	0.0190 (8)	0.0190 (7)	−0.0024 (6)	0.0024 (6)	−0.0014 (7)
C2	0.0210 (8)	0.0200 (9)	0.0190 (8)	−0.0014 (6)	0.0027 (6)	0.0020 (6)
C3	0.0179 (7)	0.0201 (9)	0.0151 (7)	−0.0003 (6)	0.0002 (6)	−0.0009 (6)
C4	0.0179 (7)	0.0221 (9)	0.0184 (8)	−0.0017 (6)	0.0014 (6)	0.0000 (7)
C5	0.0195 (7)	0.0218 (9)	0.0165 (7)	−0.0013 (6)	0.0024 (6)	0.0023 (6)
C6	0.0184 (7)	0.0168 (8)	0.0167 (8)	0.0007 (6)	0.0022 (6)	−0.0012 (6)
C7	0.0181 (7)	0.0184 (8)	0.0177 (8)	0.0015 (6)	0.0026 (6)	−0.0022 (6)
C8	0.0178 (7)	0.0297 (10)	0.0183 (8)	0.0015 (7)	0.0004 (6)	0.0025 (7)
C9	0.0211 (8)	0.0194 (9)	0.0170 (7)	0.0006 (6)	0.0031 (6)	0.0022 (6)
C10	0.0185 (7)	0.0176 (8)	0.0153 (7)	0.0011 (6)	0.0018 (6)	0.0001 (6)
C11	0.0220 (8)	0.0202 (9)	0.0160 (8)	0.0034 (6)	0.0044 (6)	0.0019 (6)
C12	0.0285 (9)	0.0196 (9)	0.0138 (7)	0.0033 (7)	0.0041 (6)	0.0002 (6)
C13	0.0242 (8)	0.0177 (8)	0.0154 (7)	0.0004 (6)	0.0002 (6)	0.0019 (6)
C14	0.0209 (8)	0.0212 (9)	0.0185 (8)	0.0033 (6)	0.0023 (6)	−0.0004 (7)
C15	0.0217 (8)	0.0201 (8)	0.0149 (7)	0.0017 (6)	0.0037 (6)	−0.0004 (6)

Br1—C3	1.8954 (17)	C5—H5A	0.9500
O1—C9	1.354 (2)	C6—C7	1.484 (2)
O1—C8	1.429 (2)	C7—C8	1.514 (3)
O2—C7	1.221 (2)	C8—H8A	0.9900
O3—C9	1.211 (2)	C8—H8B	0.9900
O4—C13	1.374 (2)	C9—C10	1.479 (2)
O4—H1O4	0.8286	C10—C15	1.393 (2)
C1—C2	1.384 (3)	C10—C11	1.403 (2)
C1—C6	1.400 (2)	C11—C12	1.382 (3)
C1—H1A	0.9500	C11—H11A	0.9500
C2—C3	1.395 (2)	C12—C13	1.394 (3)
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.385 (3)	C13—C14	1.395 (3)
C4—C5	1.388 (2)	C14—C15	1.387 (2)
C4—H4A	0.9500	C14—H14A	0.9500
C5—C6	1.399 (2)	C15—H15A	0.9500
C9—O1—C8	115.84 (15)	C7—C8—H8A	109.1
C13—O4—H1O4	104.1	O1—C8—H8B	109.1
C2—C1—C6	120.74 (16)	C7—C8—H8B	109.1
C2—C1—H1A	119.6	H8A—C8—H8B	107.9
C6—C1—H1A	119.6	O3—C9—O1	122.84 (17)
C1—C2—C3	118.57 (17)	O3—C9—C10	125.39 (17)
C1—C2—H2A	120.7	O1—C9—C10	111.77 (15)
C3—C2—H2A	120.7	C15—C10—C11	119.19 (16)
C4—C3—C2	121.84 (16)	C15—C10—C9	118.33 (16)
C4—C3—Br1	118.48 (13)	C11—C10—C9	122.48 (16)
C2—C3—Br1	119.67 (14)	C12—C11—C10	120.00 (17)
C3—C4—C5	119.05 (16)	C12—C11—H11A	120.0
C3—C4—H4A	120.5	C10—C11—H11A	120.0
C5—C4—H4A	120.5	C11—C12—C13	120.42 (17)
C4—C5—C6	120.35 (17)	C11—C12—H12A	119.8
C4—C5—H5A	119.8	C13—C12—H12A	119.8
C6—C5—H5A	119.8	O4—C13—C12	116.55 (16)
C5—C6—C1	119.40 (16)	O4—C13—C14	123.48 (16)
C5—C6—C7	121.80 (16)	C12—C13—C14	119.96 (16)
C1—C6—C7	118.78 (16)	C15—C14—C13	119.49 (17)
O2—C7—C6	122.43 (17)	C15—C14—H14A	120.3
O2—C7—C8	120.28 (16)	C13—C14—H14A	120.3
C6—C7—C8	117.30 (15)	C14—C15—C10	120.91 (16)
O1—C8—C7	112.40 (15)	C14—C15—H15A	119.5
O1—C8—H8A	109.1	C10—C15—H15A	119.5
C6—C1—C2—C3	1.4 (3)	C8—O1—C9—O3	2.6 (3)
C1—C2—C3—C4	−2.1 (3)	C8—O1—C9—C10	−177.10 (15)
C1—C2—C3—Br1	177.19 (14)	O3—C9—C10—C15	4.2 (3)
C2—C3—C4—C5	0.9 (3)	O1—C9—C10—C15	−176.10 (16)
Br1—C3—C4—C5	−178.33 (14)	O3—C9—C10—C11	−175.77 (19)
C3—C4—C5—C6	0.9 (3)	O1—C9—C10—C11	3.9 (3)
C4—C5—C6—C1	−1.5 (3)	C15—C10—C11—C12	1.2 (3)
C4—C5—C6—C7	177.18 (17)	C9—C10—C11—C12	−178.79 (18)
C2—C1—C6—C5	0.4 (3)	C10—C11—C12—C13	0.1 (3)
C2—C1—C6—C7	−178.38 (17)	C11—C12—C13—O4	179.19 (17)
C5—C6—C7—O2	−173.81 (18)	C11—C12—C13—C14	−0.9 (3)
C1—C6—C7—O2	4.9 (3)	O4—C13—C14—C15	−179.65 (17)
C5—C6—C7—C8	5.8 (3)	C12—C13—C14—C15	0.5 (3)
C1—C6—C7—C8	−175.45 (16)	C13—C14—C15—C10	0.8 (3)
C9—O1—C8—C7	−79.3 (2)	C11—C10—C15—C14	−1.7 (3)
O2—C7—C8—O1	5.1 (3)	C9—C10—C15—C14	178.32 (17)
C6—C7—C8—O1	−174.58 (15)

Cg2 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O2i	0.83	1.97	2.7961 (19)	177
C12—H12A···Br1ii	0.95	2.90	3.7938 (18)	158
C14—H14A···O2i	0.95	2.52	3.198 (2)	129
C15—H15A···Cg2i	0.95	2.86	3.6181 (18)	137

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
O4—H1O4⋯O2i	0.83	1.97	2.7961 (19)	177
C12—H12A⋯Br1ii	0.95	2.90	3.7938 (18)	158
C14—H14A⋯O2i	0.95	2.52	3.198 (2)	129
C15—H15A⋯Cg2i	0.95	2.86	3.6181 (18)	137

Symmetry codes: (i) ; (ii) .