5-Chloro-2-hy-droxy-benzoic acid.

The asymmetric unit of the title compound, C(7)H(5)ClO(3), contains two mol-ecules; both feature an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, both mol-ecules form inversion dimers linked by pairs of O-H⋯O hydrogen bonds with R(2) (2)(8) ring motifs. The dimers are inter-linked by C-H⋯O inter-actions.

Related literature

For biological background, see: Bright et al. (2010 ▶): Fattorusso et al. (2005 ▶); Miki et al. (2002 ▶). For a related structure, see: Raza et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H5ClO3

M = 172.56

Monoclinic,

a = 23.526 (2) Å

b = 3.7972 (4) Å

c = 16.7321 (16) Å

β = 104.852 (5)°

V = 1444.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.48 mm−1

T = 296 K

0.34 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.879, T max = 0.888

14048 measured reflections

3697 independent reflections

2444 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.138

S = 1.03

3697 reflections

211 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042042/hb5691sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042042/hb5691Isup2.hkl

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

C7H5ClO3	F(000) = 704
Mr = 172.56	Dx = 1.587 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 931 reflections
a = 23.526 (2) Å	θ = 2.8–26.0°
b = 3.7972 (4) Å	µ = 0.48 mm−1
c = 16.7321 (16) Å	T = 296 K
β = 104.852 (5)°	Needle, light yellow
V = 1444.8 (2) Å3	0.34 × 0.12 × 0.10 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	3697 independent reflections
Radiation source: fine-focus sealed tube	2444 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 7.40 pixels mm-1	θmax = 28.7°, θmin = 3.6°
ω scans	h = −31→31
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −4→5
Tmin = 0.879, Tmax = 0.888	l = −22→22
14048 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.073P)2] where P = (Fo2 + 2Fc2)/3
3697 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.37512 (3)	0.69966 (16)	0.07736 (3)	0.0501 (2)
O1	0.49060 (7)	0.6286 (5)	0.38781 (10)	0.0531 (6)
O2	0.43512 (7)	0.3536 (5)	0.45885 (9)	0.0497 (5)
O3	0.32656 (7)	0.1864 (5)	0.38353 (10)	0.0504 (6)
C1	0.44188 (9)	0.4711 (6)	0.39317 (12)	0.0372 (6)
C2	0.39581 (8)	0.4495 (5)	0.31555 (11)	0.0325 (6)
C3	0.34043 (9)	0.3106 (5)	0.31526 (13)	0.0363 (6)
C4	0.29691 (10)	0.3000 (6)	0.24180 (14)	0.0427 (7)
C5	0.30768 (9)	0.4181 (6)	0.16973 (13)	0.0425 (7)
C6	0.36245 (9)	0.5504 (5)	0.16965 (12)	0.0359 (6)
C7	0.40631 (9)	0.5677 (5)	0.24125 (12)	0.0355 (6)
Cl2	0.13798 (3)	0.73267 (17)	0.21674 (4)	0.0624 (3)
O4	0.01191 (7)	0.1719 (5)	0.39980 (11)	0.0604 (6)
O5	0.06701 (7)	0.1273 (5)	0.52956 (10)	0.0553 (6)
O6	0.17545 (7)	0.3485 (5)	0.56545 (10)	0.0538 (6)
C8	0.06128 (9)	0.2160 (6)	0.45705 (14)	0.0402 (7)
C9	0.10935 (9)	0.3749 (5)	0.42825 (12)	0.0349 (6)
C10	0.16403 (9)	0.4322 (6)	0.48436 (13)	0.0383 (7)
C11	0.20911 (9)	0.5788 (6)	0.45616 (14)	0.0447 (7)
C12	0.20146 (10)	0.6683 (6)	0.37478 (15)	0.0453 (8)
C13	0.14736 (10)	0.6137 (6)	0.31970 (13)	0.0413 (7)
C14	0.10148 (9)	0.4679 (6)	0.34525 (13)	0.0397 (7)
H1	0.5163 (12)	0.635 (7)	0.4326 (18)	0.0636*
H3	0.3557 (12)	0.189 (7)	0.4210 (18)	0.0604*
H4	0.25996	0.21164	0.24137	0.0512*
H5	0.27810	0.40924	0.12074	0.0510*
H7	0.44297	0.65761	0.24065	0.0425*
H4A	−0.0156 (12)	0.058 (8)	0.4222 (16)	0.0725*
H6	0.1424 (13)	0.258 (7)	0.5696 (19)	0.0646*
H11	0.24542	0.61752	0.49328	0.0536*
H12	0.23233	0.76478	0.35677	0.0543*
H14	0.06536	0.43138	0.30750	0.0476*

	U11	U22	U33	U12	U13	U23
Cl1	0.0588 (4)	0.0597 (4)	0.0332 (3)	−0.0012 (3)	0.0142 (3)	0.0039 (2)
O1	0.0349 (9)	0.0858 (13)	0.0354 (9)	−0.0154 (8)	0.0034 (7)	0.0057 (8)
O2	0.0443 (9)	0.0749 (11)	0.0300 (8)	−0.0096 (8)	0.0096 (7)	0.0028 (7)
O3	0.0427 (10)	0.0719 (11)	0.0399 (9)	−0.0131 (8)	0.0167 (7)	0.0048 (8)
C1	0.0340 (11)	0.0433 (12)	0.0359 (10)	−0.0004 (9)	0.0119 (9)	−0.0002 (9)
C2	0.0314 (10)	0.0349 (10)	0.0318 (10)	0.0006 (8)	0.0092 (8)	−0.0018 (8)
C3	0.0356 (11)	0.0370 (11)	0.0395 (11)	−0.0004 (9)	0.0153 (9)	−0.0010 (8)
C4	0.0324 (11)	0.0477 (13)	0.0473 (13)	−0.0058 (9)	0.0091 (10)	−0.0004 (9)
C5	0.0358 (12)	0.0474 (13)	0.0405 (12)	−0.0017 (10)	0.0028 (9)	−0.0011 (9)
C6	0.0408 (11)	0.0353 (10)	0.0319 (10)	0.0017 (9)	0.0098 (9)	−0.0008 (8)
C7	0.0331 (11)	0.0386 (11)	0.0358 (10)	−0.0009 (9)	0.0109 (8)	−0.0028 (8)
Cl2	0.0825 (5)	0.0671 (5)	0.0442 (3)	−0.0108 (3)	0.0284 (3)	0.0069 (3)
O4	0.0345 (9)	0.0962 (14)	0.0511 (10)	−0.0143 (9)	0.0121 (8)	0.0148 (9)
O5	0.0414 (9)	0.0852 (13)	0.0429 (9)	−0.0100 (8)	0.0173 (7)	0.0136 (8)
O6	0.0402 (9)	0.0821 (12)	0.0387 (9)	−0.0076 (9)	0.0093 (7)	0.0030 (8)
C8	0.0313 (11)	0.0481 (13)	0.0447 (12)	0.0001 (9)	0.0159 (10)	0.0023 (9)
C9	0.0326 (11)	0.0374 (11)	0.0386 (11)	0.0008 (9)	0.0163 (9)	0.0002 (8)
C10	0.0357 (11)	0.0429 (12)	0.0378 (11)	0.0017 (9)	0.0123 (9)	−0.0023 (9)
C11	0.0317 (11)	0.0528 (14)	0.0499 (13)	−0.0065 (10)	0.0113 (10)	−0.0034 (10)
C12	0.0413 (13)	0.0420 (12)	0.0597 (15)	−0.0090 (10)	0.0261 (11)	−0.0056 (10)
C13	0.0517 (14)	0.0385 (11)	0.0400 (11)	−0.0019 (10)	0.0230 (10)	−0.0004 (9)
C14	0.0374 (11)	0.0450 (12)	0.0386 (11)	−0.0018 (9)	0.0130 (9)	0.0005 (9)

Cl1—C6	1.741 (2)	C4—C5	1.370 (3)
Cl2—C13	1.740 (2)	C5—C6	1.383 (3)
O1—C1	1.316 (3)	C6—C7	1.368 (3)
O2—C1	1.234 (3)	C4—H4	0.9300
O3—C3	1.351 (3)	C5—H5	0.9300
O1—H1	0.83 (3)	C7—H7	0.9300
O3—H3	0.80 (3)	C8—C9	1.468 (3)
O4—C8	1.313 (3)	C9—C14	1.399 (3)
O5—C8	1.233 (3)	C9—C10	1.402 (3)
O6—C10	1.352 (3)	C10—C11	1.383 (3)
O4—H4A	0.93 (3)	C11—C12	1.370 (3)
O6—H6	0.87 (3)	C12—C13	1.382 (3)
C1—C2	1.465 (3)	C13—C14	1.375 (3)
C2—C7	1.402 (3)	C11—H11	0.9300
C2—C3	1.404 (3)	C12—H12	0.9300
C3—C4	1.384 (3)	C14—H14	0.9300
C1—O1—H1	113.3 (19)	C6—C7—H7	120.00
C3—O3—H3	108 (2)	C2—C7—H7	120.00
C8—O4—H4A	109.9 (16)	O5—C8—C9	122.4 (2)
C10—O6—H6	103 (2)	O4—C8—C9	115.14 (19)
O1—C1—C2	115.11 (17)	O4—C8—O5	122.4 (2)
O2—C1—C2	122.3 (2)	C8—C9—C14	120.85 (19)
O1—C1—O2	122.58 (19)	C8—C9—C10	119.74 (18)
C1—C2—C7	120.64 (18)	C10—C9—C14	119.4 (2)
C3—C2—C7	119.43 (18)	O6—C10—C11	117.7 (2)
C1—C2—C3	119.93 (17)	O6—C10—C9	123.2 (2)
C2—C3—C4	119.24 (19)	C9—C10—C11	119.09 (19)
O3—C3—C4	117.2 (2)	C10—C11—C12	121.5 (2)
O3—C3—C2	123.58 (19)	C11—C12—C13	119.3 (2)
C3—C4—C5	120.7 (2)	Cl2—C13—C12	118.86 (18)
C4—C5—C6	120.2 (2)	Cl2—C13—C14	120.14 (17)
Cl1—C6—C7	119.94 (17)	C12—C13—C14	121.0 (2)
C5—C6—C7	120.69 (19)	C9—C14—C13	119.7 (2)
Cl1—C6—C5	119.37 (16)	C10—C11—H11	119.00
C2—C7—C6	119.77 (19)	C12—C11—H11	119.00
C5—C4—H4	120.00	C11—C12—H12	120.00
C3—C4—H4	120.00	C13—C12—H12	120.00
C4—C5—H5	120.00	C9—C14—H14	120.00
C6—C5—H5	120.00	C13—C14—H14	120.00
O1—C1—C2—C3	−175.24 (19)	O4—C8—C9—C10	−179.8 (2)
O1—C1—C2—C7	4.5 (3)	O4—C8—C9—C14	−0.2 (3)
O2—C1—C2—C3	4.0 (3)	O5—C8—C9—C10	−0.4 (3)
O2—C1—C2—C7	−176.3 (2)	O5—C8—C9—C14	179.1 (2)
C1—C2—C3—O3	−1.1 (3)	C8—C9—C10—O6	−0.1 (3)
C1—C2—C3—C4	178.4 (2)	C8—C9—C10—C11	179.3 (2)
C7—C2—C3—O3	179.12 (19)	C14—C9—C10—O6	−179.7 (2)
C7—C2—C3—C4	−1.3 (3)	C14—C9—C10—C11	−0.2 (3)
C1—C2—C7—C6	−178.98 (19)	C8—C9—C14—C13	−179.5 (2)
C3—C2—C7—C6	0.8 (3)	C10—C9—C14—C13	0.1 (3)
O3—C3—C4—C5	−179.4 (2)	O6—C10—C11—C12	179.4 (2)
C2—C3—C4—C5	1.0 (3)	C9—C10—C11—C12	−0.1 (3)
C3—C4—C5—C6	−0.1 (3)	C10—C11—C12—C13	0.5 (3)
C4—C5—C6—Cl1	−179.91 (18)	C11—C12—C13—Cl2	179.34 (18)
C4—C5—C6—C7	−0.5 (3)	C11—C12—C13—C14	−0.7 (3)
Cl1—C6—C7—C2	179.56 (15)	Cl2—C13—C14—C9	−179.65 (17)
C5—C6—C7—C2	0.2 (3)	C12—C13—C14—C9	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.83 (3)	1.88 (3)	2.710 (2)	171 (3)
O3—H3···O2	0.80 (3)	1.92 (3)	2.620 (2)	146 (3)
O4—H4A···O5ii	0.93 (3)	1.76 (3)	2.694 (2)	175 (2)
O6—H6···O5	0.87 (3)	1.80 (3)	2.606 (2)	154 (3)
C5—H5···O6iii	0.93	2.55	3.311 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.83 (3)	1.88 (3)	2.710 (2)	171 (3)
O3—H3⋯O2	0.80 (3)	1.92 (3)	2.620 (2)	146 (3)
O4—H4A⋯O5ii	0.93 (3)	1.76 (3)	2.694 (2)	175 (2)
O6—H6⋯O5	0.87 (3)	1.80 (3)	2.606 (2)	154 (3)
C5—H5⋯O6iii	0.93	2.55	3.311 (3)	139

Symmetry codes: (i) ; (ii) ; (iii) .