3,7-Dichloro-quinoline-8-carboxylic acid.

THE TITLE COMPOUND (TRADE NAME: quinclorac), C(10)H(5)Cl(2)NO(2), was crystallized from a dimethyl sulfoxide solution. Quinclorac mol-ecules are packed mainly via π-π stacking inter-actions between neighbouring heterocycles (interplanar distance: 3.31 Å) and via O-H⋯N hydrogen bonding.

Related literature

For the use of 3,7-dichloro­quinoline-8-carboxylic acid as a herbicide, see: Nuria et al. (1997 ▶); Pornprom et al. (2006 ▶); Sunohara & Matsumoto (2004 ▶); Tresch & Grossmann (2002 ▶). For related complexes, see: Li et al. (2008 ▶); Turel et al. (2004 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

C10H5Cl2NO2

M = 242.05

Triclinic,

a = 7.5002 (12) Å

b = 8.4016 (14) Å

c = 8.732 (3) Å

α = 102.529 (6)°

β = 93.439 (6)°

γ = 116.479 (4)°

V = 472.98 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.66 mm−1

T = 173 (2) K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.84, T max = 0.88

5948 measured reflections

1834 independent reflections

1102 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.140

S = 1.01

1834 reflections

139 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026238/zl2136sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026238/zl2136Isup2.hkl

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

C10H5Cl2NO2	Z = 2
Mr = 242.05	F000 = 244
Triclinic, P1	Dx = 1.700 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.5002 (12) Å	Cell parameters from 958 reflections
b = 8.4016 (14) Å	θ = 2.1–25.5º
c = 8.732 (3) Å	µ = 0.66 mm−1
α = 102.529 (6)º	T = 173 (2) K
β = 93.439 (6)º	Prismlike, colorless
γ = 116.479 (4)º	0.26 × 0.22 × 0.20 mm
V = 472.98 (17) Å3

Bruker SMART APEXII diffractometer	1834 independent reflections
Radiation source: fine-focus sealed tube	1102 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.067
T = 173(2) K	θmax = 26.0º
ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −9→9
Tmin = 0.84, Tmax = 0.88	k = −8→10
5948 measured reflections	l = −10→10

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)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.062P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1834 reflections	Δρmax = 0.30 e Å−3
139 parameters	Δρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.3476 (6)	0.5471 (6)	0.2465 (5)	0.0354 (10)
H1	0.3861	0.5957	0.1583	0.043*
C2	0.2932 (6)	0.3616 (6)	0.2276 (5)	0.0324 (9)
C3	0.2343 (6)	0.2876 (6)	0.3515 (5)	0.0337 (10)
H3	0.1963	0.1613	0.3413	0.040*
C4	0.1686 (6)	0.3342 (6)	0.6269 (5)	0.0369 (10)
H4	0.1286	0.2086	0.6220	0.044*
C5	0.1655 (7)	0.4475 (6)	0.7605 (5)	0.0363 (10)
H5	0.1215	0.4011	0.8489	0.044*
C6	0.2272 (6)	0.6342 (6)	0.7699 (5)	0.0308 (9)
C7	0.2918 (6)	0.7078 (5)	0.6455 (5)	0.0253 (8)
C8	0.2910 (5)	0.5882 (5)	0.5036 (5)	0.0261 (8)
C9	0.2304 (6)	0.4002 (5)	0.4943 (5)	0.0261 (8)
C10	0.3645 (6)	0.9105 (5)	0.6610 (4)	0.0293 (9)
Cl1	0.29545 (15)	0.22889 (15)	0.04666 (12)	0.0385 (3)
Cl2	0.23077 (17)	0.77619 (16)	0.94953 (12)	0.0422 (3)
N1	0.3496 (5)	0.6591 (4)	0.3774 (4)	0.0283 (7)
O1	0.5586 (4)	0.9997 (4)	0.6659 (3)	0.0302 (6)
H1A	0.597 (7)	1.106 (7)	0.652 (5)	0.036*
O2	0.2510 (5)	0.9766 (4)	0.6634 (5)	0.0519 (9)

	U11	U22	U33	U12	U13	U23
C1	0.038 (2)	0.041 (3)	0.032 (2)	0.021 (2)	0.0079 (18)	0.012 (2)
C2	0.027 (2)	0.032 (2)	0.039 (2)	0.0174 (19)	0.0036 (17)	0.0030 (19)
C3	0.033 (2)	0.021 (2)	0.049 (2)	0.016 (2)	0.0051 (19)	0.008 (2)
C4	0.037 (2)	0.025 (2)	0.053 (3)	0.014 (2)	0.006 (2)	0.022 (2)
C5	0.043 (2)	0.035 (3)	0.036 (2)	0.019 (2)	0.0106 (19)	0.017 (2)
C6	0.0262 (19)	0.035 (2)	0.033 (2)	0.0165 (18)	0.0041 (16)	0.0098 (19)
C7	0.028 (2)	0.020 (2)	0.032 (2)	0.0138 (17)	0.0062 (16)	0.0073 (17)
C8	0.0180 (18)	0.024 (2)	0.034 (2)	0.0095 (16)	0.0014 (15)	0.0050 (17)
C9	0.0258 (18)	0.020 (2)	0.036 (2)	0.0126 (16)	0.0030 (16)	0.0091 (17)
C10	0.034 (2)	0.025 (2)	0.0246 (19)	0.0119 (18)	0.0010 (15)	0.0038 (18)
Cl1	0.0372 (6)	0.0432 (7)	0.0423 (6)	0.0303 (5)	0.0101 (5)	−0.0006 (5)
Cl2	0.0548 (7)	0.0433 (7)	0.0343 (6)	0.0280 (6)	0.0144 (5)	0.0089 (5)
N1	0.0318 (18)	0.0235 (18)	0.0295 (17)	0.0130 (15)	0.0066 (13)	0.0069 (15)
O1	0.0319 (16)	0.0189 (15)	0.0364 (16)	0.0071 (13)	0.0056 (12)	0.0120 (13)
O2	0.048 (2)	0.0257 (17)	0.092 (3)	0.0240 (16)	0.0204 (18)	0.0171 (18)

C1—N1	1.308 (5)	C5—H5	0.9500
C1—C2	1.391 (6)	C6—C7	1.373 (6)
C1—H1	0.9500	C6—Cl2	1.743 (4)
C2—C3	1.362 (6)	C7—C8	1.414 (5)
C2—Cl1	1.731 (4)	C7—C10	1.510 (5)
C3—C9	1.403 (6)	C8—N1	1.369 (5)
C3—H3	0.9500	C8—C9	1.417 (5)
C4—C5	1.345 (6)	C10—O2	1.206 (5)
C4—C9	1.405 (5)	C10—O1	1.299 (5)
C4—H4	0.9500	O1—H1A	0.84 (5)
C5—C6	1.405 (6)
N1—C1—C2	124.6 (4)	C7—C6—Cl2	119.9 (3)
N1—C1—H1	117.7	C5—C6—Cl2	118.0 (3)
C2—C1—H1	117.7	C6—C7—C8	117.8 (4)
C3—C2—C1	118.9 (4)	C6—C7—C10	121.0 (3)
C3—C2—Cl1	121.5 (3)	C8—C7—C10	121.2 (3)
C1—C2—Cl1	119.6 (3)	N1—C8—C7	118.2 (4)
C2—C3—C9	119.2 (4)	N1—C8—C9	121.6 (3)
C2—C3—H3	120.4	C7—C8—C9	120.2 (4)
C9—C3—H3	120.4	C3—C9—C4	122.9 (4)
C5—C4—C9	120.5 (4)	C3—C9—C8	118.0 (4)
C5—C4—H4	119.7	C4—C9—C8	119.1 (3)
C9—C4—H4	119.7	O2—C10—O1	125.4 (4)
C4—C5—C6	120.2 (4)	O2—C10—C7	122.5 (3)
C4—C5—H5	119.9	O1—C10—C7	112.1 (3)
C6—C5—H5	119.9	C1—N1—C8	117.7 (3)
C7—C6—C5	122.1 (4)	C10—O1—H1A	113 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1i	0.84 (5)	1.91 (5)	2.753 (4)	173 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.84 (5)	1.91 (5)	2.753 (4)	173 (4)

Symmetry code: (i) .