2-(2-Chloro-phen-yl)acetic acid.

In the title compound, C(8)H(7)ClO(2), the carboxyl group forms a dihedral angle of 74.83 (9)° with the benzene ring plane. In the crystal, mol-ecules are linked into inversion dimers by pairs of O-H⋯O hydrogen bonds. The dimers are linked into layers parallel to the bc plane by weak C-H⋯O inter-actions.

Related literature

For applications of phenyl­acetic acids, see: Castellari & Ottani (1995 ▶); Deshpande et al. (2008 ▶); Hata et al. (1986 ▶). For the crystal structure of isostructural 2-(2-bromo­phen­yl)acetic acid, see: Kant et al. (2012 ▶).

Experimental

Crystal data

C8H7ClO2

M = 170.59

Monoclinic,

a = 9.1473 (7) Å

b = 5.8265 (3) Å

c = 15.4299 (7) Å

β = 101.155 (5)°

V = 806.83 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.42 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 ▶) T min = 0.748, T max = 1.000

9367 measured reflections

1583 independent reflections

1173 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.145

S = 1.06

1583 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812023938/gk2495sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023938/gk2495Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023938/gk2495Isup3.cml

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

C8H7ClO2	F(000) = 352
Mr = 170.59	Dx = 1.404 Mg m−3
Monoclinic, P21/c	Melting point = 369–366 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.1473 (7) Å	Cell parameters from 3981 reflections
b = 5.8265 (3) Å	θ = 3.5–29.1°
c = 15.4299 (7) Å	µ = 0.42 mm−1
β = 101.155 (5)°	T = 293 K
V = 806.83 (8) Å3	Block, colourless
Z = 4	0.3 × 0.2 × 0.2 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1583 independent reflections
Radiation source: fine-focus sealed tube	1173 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.8°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→7
Tmin = 0.748, Tmax = 1.000	l = −19→19
9367 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0608P)2 + 0.4607P] where P = (Fo2 + 2Fc2)/3
1583 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.58539 (10)	0.25918 (15)	0.57120 (5)	0.0721 (3)
C1	0.7450 (3)	0.0180 (4)	0.70745 (16)	0.0451 (6)
C2	0.6591 (3)	0.2111 (4)	0.68252 (16)	0.0447 (6)
C3	0.6269 (3)	0.3678 (5)	0.74270 (18)	0.0516 (7)
H3	0.5691	0.4962	0.7238	0.062*
C4	0.6811 (4)	0.3324 (5)	0.8313 (2)	0.0599 (8)
H4	0.6599	0.4369	0.8727	0.072*
C5	0.7665 (4)	0.1427 (6)	0.85832 (19)	0.0657 (9)
H5	0.8028	0.1180	0.9182	0.079*
C6	0.7986 (4)	−0.0111 (5)	0.79697 (19)	0.0602 (8)
H6	0.8577	−0.1380	0.8162	0.072*
C7	0.7754 (4)	−0.1586 (5)	0.6417 (2)	0.0604 (8)
H7A	0.8219	−0.2908	0.6740	0.073*
H7B	0.6808	−0.2086	0.6070	0.073*
C8	0.8723 (3)	−0.0803 (5)	0.57996 (18)	0.0527 (7)
O9	0.9496 (2)	0.0930 (4)	0.59199 (13)	0.0672 (6)
O10	0.8700 (3)	−0.2177 (4)	0.51387 (14)	0.0729 (7)
H10	0.9245	−0.1674	0.4820	0.109*

	U11	U22	U33	U12	U13	U23
Cl1	0.0835 (7)	0.0807 (6)	0.0476 (4)	−0.0019 (4)	0.0015 (4)	0.0124 (4)
C1	0.0496 (16)	0.0395 (13)	0.0501 (14)	−0.0030 (11)	0.0193 (12)	0.0039 (11)
C2	0.0466 (15)	0.0484 (15)	0.0403 (12)	−0.0089 (12)	0.0117 (11)	0.0049 (11)
C3	0.0537 (17)	0.0421 (14)	0.0629 (16)	0.0005 (12)	0.0206 (13)	0.0032 (13)
C4	0.070 (2)	0.0558 (17)	0.0571 (17)	−0.0072 (15)	0.0218 (15)	−0.0096 (14)
C5	0.076 (2)	0.077 (2)	0.0423 (14)	−0.0015 (18)	0.0081 (14)	0.0044 (15)
C6	0.065 (2)	0.0565 (17)	0.0597 (17)	0.0089 (15)	0.0142 (14)	0.0149 (14)
C7	0.076 (2)	0.0430 (15)	0.0692 (18)	−0.0054 (15)	0.0318 (16)	−0.0039 (14)
C8	0.0549 (17)	0.0486 (15)	0.0576 (16)	−0.0054 (14)	0.0184 (13)	−0.0096 (13)
O9	0.0748 (15)	0.0647 (13)	0.0710 (13)	−0.0229 (12)	0.0362 (11)	−0.0244 (11)
O10	0.0876 (17)	0.0699 (14)	0.0708 (14)	−0.0292 (12)	0.0393 (12)	−0.0291 (11)

Cl1—C2	1.742 (3)	C5—C6	1.376 (4)
C1—C2	1.384 (4)	C5—H5	0.9300
C1—C6	1.384 (4)	C6—H6	0.9300
C1—C7	1.508 (4)	C7—C8	1.492 (4)
C2—C3	1.374 (4)	C7—H7A	0.9700
C3—C4	1.377 (4)	C7—H7B	0.9700
C3—H3	0.9300	C8—O9	1.227 (3)
C4—C5	1.370 (5)	C8—O10	1.293 (3)
C4—H4	0.9300	O10—H10	0.8200
C2—C1—C6	116.7 (2)	C6—C5—H5	120.0
C2—C1—C7	122.4 (2)	C5—C6—C1	121.7 (3)
C6—C1—C7	120.8 (3)	C5—C6—H6	119.1
C3—C2—C1	122.5 (2)	C1—C6—H6	119.1
C3—C2—Cl1	117.8 (2)	C8—C7—C1	115.5 (2)
C1—C2—Cl1	119.7 (2)	C8—C7—H7A	108.4
C2—C3—C4	119.2 (3)	C1—C7—H7A	108.4
C2—C3—H3	120.4	C8—C7—H7B	108.4
C4—C3—H3	120.4	C1—C7—H7B	108.4
C5—C4—C3	119.8 (3)	H7A—C7—H7B	107.5
C5—C4—H4	120.1	O9—C8—O10	123.3 (3)
C3—C4—H4	120.1	O9—C8—C7	123.5 (2)
C4—C5—C6	120.1 (3)	O10—C8—C7	113.2 (2)
C4—C5—H5	120.0	C8—O10—H10	109.5
C6—C1—C2—C3	−0.2 (4)	C4—C5—C6—C1	−0.9 (5)
C7—C1—C2—C3	177.6 (3)	C2—C1—C6—C5	0.8 (4)
C6—C1—C2—Cl1	−179.2 (2)	C7—C1—C6—C5	−177.0 (3)
C7—C1—C2—Cl1	−1.4 (4)	C2—C1—C7—C8	68.3 (4)
C1—C2—C3—C4	−0.3 (4)	C6—C1—C7—C8	−114.0 (3)
Cl1—C2—C3—C4	178.8 (2)	C1—C7—C8—O9	15.7 (5)
C2—C3—C4—C5	0.2 (4)	C1—C7—C8—O10	−166.3 (3)
C3—C4—C5—C6	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O9i	0.82	1.82	2.639 (4)	173
C6—H6···O9ii	0.93	2.57	3.469 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10⋯O9i	0.82	1.82	2.639 (4)	173
C6—H6⋯O9ii	0.93	2.57	3.469 (4)	163

Symmetry codes: (i) ; (ii) .