2-(4-Bromo­phen­yl)-2-oxoethyl 4-hy­droxy­benzoate

Fun, H.-K.; Loh, W.-S.; Garudachari, B.; Isloor, A.M.; Satyanarayana, M.N.

doi:10.1107/S1600536811040311

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2854

doi:10.1107/S1600536811040311

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2-(4-Bromophenyl)-2-oxoethyl 4-hydroxybenzoate

Hoong-Kun Fun,^a ^*‡ Wan-Sin Loh,^a § B. Garudachari,^b Arun M. Isloor ^b and M. N. Satyanarayana ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bOrganic Electronics Division, Department of Chemistry, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India, and ^cDepartment of Physics, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 29 September 2011; accepted 30 September 2011; online 5 October 2011)

In the title compound, C₁₅H₁₁BrO₄, 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 molecules, forming layers lying parallel to (101). The crystal packing is further consolidated by C—H⋯π interactions and π–π stacking interactions [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_r = 335.15
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.086
S = 1.04
4700 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.42 e Å⁻³

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) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811040311/hb6429sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811040311/hb6429Isup3.cml

checkCIF report

Comment top

As part of our ongoing structural studies of phenacyl benzoates (Fun et al., 2011), we now report the crystal structure of the title compound.

In the title compound (Fig. 1), the dihedral angle formed between the bromo-substituted (C1–C6) and hydroxy-substituted (C10–C15) benzene rings is 66.77 (8)°. Bond lengths and angles are within the normal ranges and are comparable to the related structure (Jin et al., 2008).

In the crystal (Fig. 2), O4—H1O4···O2, C12—H12A···Br1 and C14—H14A···O2 hydrogen bonds (Table 1) link the molecules to form layers parallel to the (101) plane. The crystal packing is further consolidated by C—H···π interactions involving the centroid of the hydroxy-substituted benzene ring (Cg2; Table 1) and π–π interactions (Table 1) involving the centroids of the substituted benzene rings with the distance of Cg1···Cg2 being 3.5476 (7) Å. Cg 1 is the centroid of the bromo-substituted benzene ring.

Related literature top

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 top

A mixture of 4-hydroxybenzoic acid (1.0 g, 0.0072 mol), potassium carbonate (1.09 g, 0.0079 mol) and 2-bromo-1-(4-bromophenyl)ethanone (2.0 g, 0.0072 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colourless needle-shaped crystals of 2-(4-bromophenyl)-2-oxoethyl 4-hydroxybenzoate began to separate out. It was collected by filtration and recrystallized from ethanol to yield colourless blocks. Yield: 2.1 g, 86.7%. M. p.: 464–465 K (Lund & Langvad, 1932).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewed along the showing the b axis. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

2-(4-Bromophenyl)-2-oxoethyl 4-hydroxybenzoate top

Crystal data top

C₁₅H₁₁BrO₄	F(000) = 672
M_r = 335.15	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0359P)² + 1.236P] where P = (F_o² + 2F_c²)/3
4700 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₅H₁₁BrO₄	V = 1297.43 (7) Å³
M_r = 335.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.2917 (2) Å	µ = 3.18 mm⁻¹
b = 7.7893 (2) Å	T = 100 K
c = 26.7497 (8) Å	0.56 × 0.27 × 0.23 mm
β = 98.234 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4700 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3640 reflections with I > 2σ(I)
T_min = 0.267, T_max = 0.535	R_int = 0.022
15470 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.04	Δρ_max = 0.74 e Å⁻³
4700 reflections	Δρ_min = −0.42 e Å⁻³
181 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, y−1/2, −z+1/2; (ii) x+1, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁BrO₄
M_r	335.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.2917 (2), 7.7893 (2), 26.7497 (8)
β (°)	98.234 (2)
V (Å³)	1297.43 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.18
Crystal size (mm)	0.56 × 0.27 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.267, 0.535
No. of measured, independent and observed [I > 2σ(I)] reflections	15470, 4700, 3640
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.086, 1.04
No. of reflections	4700
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.42

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SAINT (Bruker, 2009, SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+2, y−1/2, −z+1/2; (ii) x+1, −y+3/2, z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7581-2009.

Acknowledgements

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a research fellowship. AMI thanks Professor Sandeep Sanchethi, Director of the National Institute of Technology–Karnataka, India, for providing research facilities and also thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for the Young Scientist award. MNS thanks the Department of Information Technology, Government of India, for financial support.

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Volume 67| Part 11| November 2011| Page o2854

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