2-(2-Chloro-phen-oxy)benzoic acid.

In the crystal structure of the title compound, C(13)H(9)ClO(3), the mol-ecules form classical O-H⋯O hydrogen-bonded carb-oxy-lic acid dimers. These dimers are linked by C-H⋯π inter-actions into a three-dimensional network. The benzene rings are oriented at a dihedral angle of 77.8 (1)°.

Related literature

For applications of the title compound, see: Yang et al. (1972 ▶). For a related structure, see: Parkin et al. (2005 ▶). For the synthesis of the title compound, see: Rolando et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H9ClO3

M = 248.65

Monoclinic,

a = 6.9930 (14) Å

b = 24.986 (5) Å

c = 7.5140 (15) Å

β = 115.79 (3)°

V = 1182.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.912, T max = 0.969

4651 measured reflections

2177 independent reflections

1061 reflections with I > 2σ(I)

R int = 0.088

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.110

S = 1.01

2177 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006301/bq2280sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006301/bq2280Isup2.hkl

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

C13H9ClO3	F(000) = 512
Mr = 248.65	Dx = 1.397 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 6.9930 (14) Å	θ = 9–14°
b = 24.986 (5) Å	µ = 0.32 mm−1
c = 7.5140 (15) Å	T = 293 K
β = 115.79 (3)°	Block, colourless
V = 1182.1 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1061 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.088
graphite	θmax = 25.4°, θmin = 1.6°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −30→30
Tmin = 0.912, Tmax = 0.969	l = −9→8
4651 measured reflections	3 standard reflections every 200 reflections
2177 independent reflections	intensity decay: 1%

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.035P)2] where P = (Fo2 + 2Fc2)/3
2177 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.31 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
Cl	0.30495 (19)	0.80926 (6)	0.11968 (19)	0.1627 (6)
O1	0.5536 (3)	0.90532 (7)	0.1714 (2)	0.0654 (6)
C1	0.5689 (5)	0.81539 (15)	0.2793 (5)	0.0820 (9)
O2	0.0554 (3)	0.99730 (8)	−0.2082 (2)	0.0756 (6)
H2B	−0.0220	1.0088	−0.1606	0.113*
C2	0.6811 (8)	0.77525 (16)	0.4047 (6)	0.1038 (13)
H2A	0.6136	0.7432	0.4050	0.125*
O3	0.2120 (3)	0.96137 (9)	0.0872 (2)	0.0780 (7)
C3	0.8874 (8)	0.78149 (18)	0.5273 (6)	0.1116 (16)
H3A	0.9597	0.7542	0.6150	0.134*
C4	0.9925 (6)	0.82717 (19)	0.5254 (5)	0.0998 (13)
H4A	1.1367	0.8308	0.6076	0.120*
C5	0.8814 (5)	0.86787 (13)	0.3997 (4)	0.0701 (9)
H5A	0.9506	0.8994	0.3967	0.084*
C6	0.6706 (5)	0.86214 (12)	0.2799 (3)	0.0533 (7)
C7	0.5230 (4)	0.91164 (10)	−0.0195 (3)	0.0499 (7)
C8	0.3564 (4)	0.94517 (10)	−0.1407 (3)	0.0492 (7)
C9	0.3345 (4)	0.95491 (11)	−0.3322 (3)	0.0608 (8)
H9A	0.2275	0.9778	−0.4143	0.073*
C10	0.4647 (5)	0.93199 (13)	−0.4018 (4)	0.0755 (9)
H10A	0.4463	0.9388	−0.5299	0.091*
C11	0.6243 (5)	0.89853 (13)	−0.2802 (4)	0.0760 (10)
H11A	0.7140	0.8826	−0.3268	0.091*
C12	0.6529 (4)	0.88827 (11)	−0.0903 (3)	0.0619 (8)
H12A	0.7608	0.8654	−0.0099	0.074*
C13	0.2020 (4)	0.96877 (11)	−0.0801 (3)	0.0492 (6)

	U11	U22	U33	U12	U13	U23
Cl	0.1046 (9)	0.1774 (14)	0.1807 (12)	−0.0608 (9)	0.0384 (8)	−0.0066 (9)
O1	0.0724 (13)	0.0844 (15)	0.0475 (10)	0.0307 (11)	0.0338 (10)	0.0141 (9)
C1	0.089 (3)	0.074 (2)	0.091 (2)	−0.002 (2)	0.046 (2)	0.0038 (19)
O2	0.0668 (14)	0.1086 (17)	0.0618 (11)	0.0366 (12)	0.0375 (11)	0.0274 (11)
C2	0.133 (4)	0.078 (3)	0.114 (3)	0.014 (3)	0.066 (3)	0.027 (2)
O3	0.0779 (14)	0.1155 (18)	0.0523 (11)	0.0450 (13)	0.0392 (10)	0.0240 (10)
C3	0.139 (4)	0.113 (4)	0.095 (3)	0.071 (3)	0.062 (3)	0.047 (3)
C4	0.073 (3)	0.146 (4)	0.076 (2)	0.045 (3)	0.028 (2)	0.018 (3)
C5	0.055 (2)	0.088 (3)	0.0663 (18)	0.0113 (18)	0.0260 (16)	0.0073 (17)
C6	0.0579 (18)	0.063 (2)	0.0439 (14)	0.0175 (17)	0.0267 (14)	0.0095 (13)
C7	0.0558 (17)	0.0591 (18)	0.0421 (14)	0.0042 (14)	0.0283 (13)	0.0022 (12)
C8	0.0453 (15)	0.0626 (19)	0.0420 (14)	0.0029 (14)	0.0210 (13)	0.0000 (12)
C9	0.0648 (19)	0.072 (2)	0.0479 (15)	0.0127 (16)	0.0267 (15)	0.0067 (13)
C10	0.091 (2)	0.096 (2)	0.0515 (17)	0.028 (2)	0.0423 (18)	0.0130 (16)
C11	0.088 (2)	0.100 (3)	0.0565 (17)	0.026 (2)	0.0459 (17)	−0.0012 (17)
C12	0.066 (2)	0.074 (2)	0.0525 (16)	0.0186 (16)	0.0320 (15)	0.0053 (14)
C13	0.0425 (15)	0.0625 (18)	0.0423 (14)	0.0026 (14)	0.0181 (12)	0.0064 (13)

Cl—C1	1.716 (3)	C5—C6	1.360 (3)
O1—C7	1.364 (3)	C5—H5A	0.9300
O1—C6	1.385 (3)	C7—C12	1.367 (3)
C1—C2	1.366 (4)	C7—C8	1.402 (3)
C1—C6	1.367 (4)	C8—C9	1.401 (3)
O2—C13	1.276 (3)	C8—C13	1.466 (3)
O2—H2B	0.8200	C9—C10	1.358 (4)
C2—C3	1.341 (5)	C9—H9A	0.9300
C2—H2A	0.9300	C10—C11	1.376 (4)
O3—C13	1.242 (2)	C10—H10A	0.9300
C3—C4	1.361 (5)	C11—C12	1.376 (3)
C3—H3A	0.9300	C11—H11A	0.9300
C4—C5	1.375 (4)	C12—H12A	0.9300
C4—H4A	0.9300
C7—O1—C6	119.41 (19)	O1—C7—C8	117.3 (2)
C2—C1—C6	118.9 (3)	C12—C7—C8	120.5 (2)
C2—C1—Cl	122.5 (3)	C9—C8—C7	117.4 (2)
C6—C1—Cl	118.6 (3)	C9—C8—C13	118.9 (2)
C13—O2—H2B	109.5	C7—C8—C13	123.7 (2)
C3—C2—C1	120.8 (4)	C10—C9—C8	122.0 (3)
C3—C2—H2A	119.6	C10—C9—H9A	119.0
C1—C2—H2A	119.6	C8—C9—H9A	119.0
C2—C3—C4	121.0 (4)	C9—C10—C11	119.1 (2)
C2—C3—H3A	119.5	C9—C10—H10A	120.4
C4—C3—H3A	119.5	C11—C10—H10A	120.4
C3—C4—C5	118.8 (4)	C10—C11—C12	120.8 (3)
C3—C4—H4A	120.6	C10—C11—H11A	119.6
C5—C4—H4A	120.6	C12—C11—H11A	119.6
C6—C5—C4	120.2 (3)	C7—C12—C11	120.2 (2)
C6—C5—H5A	119.9	C7—C12—H12A	119.9
C4—C5—H5A	119.9	C11—C12—H12A	119.9
C5—C6—C1	120.3 (3)	O3—C13—O2	121.3 (2)
C5—C6—O1	120.0 (3)	O3—C13—C8	122.0 (2)
C1—C6—O1	119.4 (3)	O2—C13—C8	116.7 (2)
O1—C7—C12	122.2 (2)
C6—C1—C2—C3	0.3 (5)	O1—C7—C8—C9	175.4 (2)
Cl—C1—C2—C3	179.9 (3)	C12—C7—C8—C9	−2.2 (4)
C1—C2—C3—C4	−2.4 (6)	O1—C7—C8—C13	−6.7 (4)
C2—C3—C4—C5	2.2 (6)	C12—C7—C8—C13	175.8 (2)
C3—C4—C5—C6	−0.1 (5)	C7—C8—C9—C10	1.7 (4)
C4—C5—C6—C1	−1.8 (4)	C13—C8—C9—C10	−176.4 (3)
C4—C5—C6—O1	172.1 (2)	C8—C9—C10—C11	−0.5 (5)
C2—C1—C6—C5	1.7 (4)	C9—C10—C11—C12	−0.1 (5)
Cl—C1—C6—C5	−177.9 (2)	O1—C7—C12—C11	−175.8 (3)
C2—C1—C6—O1	−172.3 (3)	C8—C7—C12—C11	1.6 (4)
Cl—C1—C6—O1	8.1 (4)	C10—C11—C12—C7	−0.4 (5)
C7—O1—C6—C5	95.1 (3)	C9—C8—C13—O3	179.5 (3)
C7—O1—C6—C1	−90.9 (3)	C7—C8—C13—O3	1.7 (4)
C6—O1—C7—C12	−21.0 (4)	C9—C8—C13—O2	−0.2 (4)
C6—O1—C7—C8	161.5 (2)	C7—C8—C13—O2	−178.1 (2)

Cg1 is the centroid of C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O3i	0.82	1.81	2.621 (3)	172
C11—H11A···Cg1ii	0.93	2.74	3.582 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O3i	0.82	1.81	2.621 (3)	172
C11—H11A⋯Cg1ii	0.93	2.74	3.582 (4)	151

Symmetry codes: (i) ; (ii) .