2-(2-Bromo­phen­yl)acetic acid

Kant, R.; Kapoor, K.; Narayana, B.

doi:10.1107/S1600536812020545

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1704

doi:10.1107/S1600536812020545

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2-(2-Bromophenyl)acetic acid

Rajni Kant,^a ^* Kamini Kapoor ^a and B. Narayana ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 30 April 2012; accepted 7 May 2012; online 12 May 2012)

In the title molecule, C₈H₇BrO₂, the carboxyl group is twisted by 76.2 (3)° from the benzene ring plane. In the crystal, molecules are linked into inversion dimers through pairs of O—H⋯O hydrogen bonds. The dimers are further linked into layers parallel to the bc plane by weak C—H⋯O hydrogen bonds.

Related literature

For applications of the title compound, see: Deshpande et al. (2008 ); Rodriguesa et al. (2002 ); Pratt et al. (2000 ). For related structures, see: Hodgson & Asplund (1991 ); Harris et al. (1994 ); Hartung et al. (2004 ); Yuan et al. (2008 ); Jasinski et al.(2010 ); Li et al. (2010 ).

Experimental

Crystal data

C₈H₇BrO₂
M_r = 215.05
Monoclinic, P 2₁ /c
a = 8.9732 (5) Å
b = 5.9114 (3) Å
c = 15.8489 (7) Å
β = 99.529 (5)°
V = 829.09 (7) Å³
Z = 4
Mo Kα radiation
μ = 4.90 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.370, T_max = 1.000
8471 measured reflections
1628 independent reflections
1248 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.096
S = 1.07
1628 reflections
105 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O9ⁱ	0.87 (7)	1.76 (7)	2.630 (4)	175 (3)
C6—H6⋯O9ⁱⁱ	0.93	2.57	3.453 (5)	158
Symmetry codes: (i) -x, -y+1, -z+2; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812020545/cv5295sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020545/cv5295Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020545/cv5295Isup3.cml

checkCIF report

Comment top

The title compound, (I), has many applications in various syntheses, for example, in the synthesis of heterocyclic compounds (Deshpande et al., 2008) and in the synthesis of AMPA antagonists - substituted quinoxalinediones, quinolones, isatinoximes and benzodiazepine derivatives (Pratt et al., 2000). It can also be used in a gas chromatography as a phase transfer catalyst (Rodriguesa et al., 2002). Herein we report its crystal structure.

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in related structures (Hodgson & Asplund,1991; Harris et al., 1994; Hartung et al., 2004; Yuan et al., 2008; Jasinski et al., 2010; Li et al., 2010). The carboxyl group is twisted at 76.2 (3)° from the benzene ring plane. Intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. Weak intermolecular C—H···O interactions (Table 1) link further these dimers into layers parallel to bc plane.

Related literature top

For applications of the title compound, see: Deshpande et al. (2008); Rodriguesa et al. (2002); Pratt et al. (2000). For related structures, see: Hodgson & Asplund (1991); Harris et al. (1994); Hartung et al. (2004); Yuan et al. (2008); Jasinski et al.(2010); Li et al. (2010).

Experimental top

The title compound was purchased from the Spectrochem Ltd., Mumbai. Single-crystals were grown from acetone and toluene(1:1) mixture by slow evaporation method.

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2010); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. ORTEP view of the molecule with the atom-labeling scheme. The Displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.

2-(2-Bromophenyl)acetic acid top

Crystal data top

C₈H₇BrO₂	F(000) = 424
M_r = 215.05	D_x = 1.723 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 381–377 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.9732 (5) Å	Cell parameters from 3025 reflections
b = 5.9114 (3) Å	θ = 3.4–29.1°
c = 15.8489 (7) Å	µ = 4.90 mm⁻¹
β = 99.529 (5)°	T = 293 K
V = 829.09 (7) Å³	Prism, white
Z = 4	0.3 × 0.2 × 0.2 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1628 independent reflections
Radiation source: fine-focus sealed tube	1248 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.7°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	k = −7→7
T_min = 0.370, T_max = 1.000	l = −19→19
8471 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0324P)² + 1.055P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
1628 reflections	Δρ_max = 0.55 e Å⁻³
105 parameters	Δρ_min = −0.69 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.071 (3)

Crystal data top

C₈H₇BrO₂	V = 829.09 (7) Å³
M_r = 215.05	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9732 (5) Å	µ = 4.90 mm⁻¹
b = 5.9114 (3) Å	T = 293 K
c = 15.8489 (7) Å	0.3 × 0.2 × 0.2 mm
β = 99.529 (5)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1628 independent reflections
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	1248 reflections with I > 2σ(I)
T_min = 0.370, T_max = 1.000	R_int = 0.043
8471 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.55 e Å⁻³
1628 reflections	Δρ_min = −0.69 e Å⁻³
105 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.42140 (6)	0.23223 (8)	0.92648 (3)	0.0681 (3)
C1	0.2498 (4)	0.4863 (6)	0.7908 (2)	0.0427 (9)
C2	0.3352 (4)	0.2936 (6)	0.8109 (2)	0.0395 (8)
C3	0.3640 (4)	0.1404 (7)	0.7497 (3)	0.0498 (10)
H3	0.4208	0.0110	0.7654	0.060*
C4	0.3078 (6)	0.1819 (8)	0.6660 (3)	0.0627 (12)
H4	0.3275	0.0813	0.6241	0.075*
C5	0.2223 (6)	0.3715 (9)	0.6430 (3)	0.0689 (13)
H5	0.1839	0.3990	0.5857	0.083*
C6	0.1935 (5)	0.5208 (7)	0.7051 (3)	0.0599 (12)
H6	0.1347	0.6480	0.6890	0.072*
C7	0.2239 (5)	0.6574 (7)	0.8568 (3)	0.0570 (11)
H7A	0.3211	0.7023	0.8887	0.068*
H7B	0.1779	0.7906	0.8276	0.068*
O8	0.1337 (4)	0.7126 (6)	0.9850 (2)	0.0710 (10)
C8	0.1266 (4)	0.5795 (7)	0.9188 (3)	0.0520 (10)
O9	0.0457 (3)	0.4130 (5)	0.9081 (2)	0.0650 (9)
H8	0.072 (7)	0.678 (10)	1.020 (5)	0.11 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0835 (4)	0.0712 (4)	0.0440 (3)	−0.0020 (2)	−0.0059 (2)	0.0091 (2)
C1	0.049 (2)	0.0354 (19)	0.047 (2)	−0.0069 (16)	0.0158 (18)	0.0034 (16)
C2	0.045 (2)	0.041 (2)	0.0330 (19)	−0.0082 (16)	0.0085 (16)	0.0050 (15)
C3	0.058 (2)	0.043 (2)	0.052 (3)	−0.0005 (18)	0.021 (2)	0.0007 (19)
C4	0.085 (3)	0.059 (3)	0.049 (3)	−0.015 (2)	0.026 (2)	−0.014 (2)
C5	0.088 (3)	0.079 (3)	0.038 (3)	−0.007 (3)	0.004 (2)	0.007 (2)
C6	0.070 (3)	0.053 (2)	0.055 (3)	0.007 (2)	0.006 (2)	0.016 (2)
C7	0.070 (3)	0.040 (2)	0.067 (3)	−0.005 (2)	0.029 (2)	−0.004 (2)
O8	0.080 (2)	0.069 (2)	0.071 (2)	−0.0264 (17)	0.0341 (19)	−0.0325 (17)
C8	0.053 (2)	0.048 (2)	0.058 (3)	−0.0015 (19)	0.019 (2)	−0.010 (2)
O9	0.0697 (19)	0.0631 (19)	0.069 (2)	−0.0253 (16)	0.0323 (16)	−0.0258 (16)

Geometric parameters (Å, º) top

Br1—C2	1.901 (4)	C5—C6	1.378 (6)
C1—C2	1.380 (5)	C5—H5	0.9300
C1—C6	1.383 (5)	C6—H6	0.9300
C1—C7	1.502 (5)	C7—C8	1.491 (6)
C2—C3	1.383 (5)	C7—H7A	0.9700
C3—C4	1.361 (6)	C7—H7B	0.9700
C3—H3	0.9300	O8—C8	1.304 (5)
C4—C5	1.373 (7)	O8—H8	0.87 (7)
C4—H4	0.9300	C8—O9	1.218 (5)

C2—C1—C6	116.6 (4)	C6—C5—H5	120.2
C2—C1—C7	122.6 (4)	C5—C6—C1	121.7 (4)
C6—C1—C7	120.8 (4)	C5—C6—H6	119.1
C1—C2—C3	122.6 (4)	C1—C6—H6	119.1
C1—C2—Br1	120.1 (3)	C8—C7—C1	115.2 (3)
C3—C2—Br1	117.2 (3)	C8—C7—H7A	108.5
C4—C3—C2	118.9 (4)	C1—C7—H7A	108.5
C4—C3—H3	120.5	C8—C7—H7B	108.5
C2—C3—H3	120.5	C1—C7—H7B	108.5
C3—C4—C5	120.4 (4)	H7A—C7—H7B	107.5
C3—C4—H4	119.8	C8—O8—H8	115 (4)
C5—C4—H4	119.8	O9—C8—O8	123.3 (4)
C4—C5—C6	119.7 (4)	O9—C8—C7	123.9 (4)
C4—C5—H5	120.2	O8—C8—C7	112.8 (4)

C6—C1—C2—C3	−0.2 (5)	C4—C5—C6—C1	0.6 (7)
C7—C1—C2—C3	−177.4 (3)	C2—C1—C6—C5	−0.6 (6)
C6—C1—C2—Br1	178.8 (3)	C7—C1—C6—C5	176.8 (4)
C7—C1—C2—Br1	1.5 (5)	C2—C1—C7—C8	−68.9 (5)
C1—C2—C3—C4	0.9 (6)	C6—C1—C7—C8	114.0 (4)
Br1—C2—C3—C4	−178.1 (3)	C1—C7—C8—O9	−15.8 (6)
C2—C3—C4—C5	−0.9 (6)	C1—C7—C8—O8	166.1 (4)
C3—C4—C5—C6	0.2 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O9ⁱ	0.87 (7)	1.76 (7)	2.630 (4)	175 (3)
C6—H6···O9ⁱⁱ	0.93	2.57	3.453 (5)	158

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₈H₇BrO₂
M_r	215.05
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.9732 (5), 5.9114 (3), 15.8489 (7)
β (°)	99.529 (5)
V (Å³)	829.09 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.90
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)
T_min, T_max	0.370, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8471, 1628, 1248
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.096, 1.07
No. of reflections	1628
No. of parameters	105
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.69

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2010), CrysAlis PRO RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O9ⁱ	0.87 (7)	1.76 (7)	2.630 (4)	175 (3)
C6—H6···O9ⁱⁱ	0.93	2.57	3.453 (5)	158

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x, y+1/2, −z+3/2.

Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003 and the University of Jammu, Jammu, India, for financial support. BN thanks the UGC for financial assistance through the SAP and BSR one-time grant for the purchase of chemicals.

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