2-Chloro-quinoline-3-carboxylic acid.

The crystal structure of the title compound, C(10)H(6)ClNO(2), can be described by two types of crossed layers which are parallel to (110) and (10). The crystal packing is stabilized by inter-molecular C-H⋯O and O-H⋯N hydrogen bonds, resulting in the formation of a two-dimensional network and reinforcing the cohesion of the structure.

Related literature

For our previous work on the preparation of α-amino­nitriles, see: Ladraa et al. (2009 ▶); Belfaitah et al. (2006 ▶). For the removal of chiral auxiliaries using ceric ammonium nitrate, see: Bhanu Prasad et al. (2004 ▶).

Experimental

Crystal data

C10H6ClNO2

M = 207.61

Orthorhombic,

a = 5.8193 (2) Å

b = 8.0689 (3) Å

c = 18.1780 (5) Å

V = 853.55 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 120 K

0.19 × 0.12 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.915, T max = 0.967

13714 measured reflections

1938 independent reflections

1746 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.094

S = 1.14

1938 reflections

129 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 862 Friedel pairs

Flack parameter: 0.28 (9)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006501/bq2197sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006501/bq2197Isup2.hkl

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

C10H6ClNO2	F(000) = 424
Mr = 207.61	Dx = 1.616 Mg m−3
Orthorhombic, P21nb	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2bc 2a	Cell parameters from 21289 reflections
a = 5.8193 (2) Å	θ = 2.9–27.5°
b = 8.0689 (3) Å	µ = 0.41 mm−1
c = 18.1780 (5) Å	T = 120 K
V = 853.55 (5) Å3	Prism, yellow
Z = 4	0.19 × 0.12 × 0.08 mm

Nonius KappaCCD diffractometer	1938 independent reflections
Radiation source: Enraf–Nonius FR590	1746 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.4°
CCD rotation images, thin slices scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −10→10
Tmin = 0.915, Tmax = 0.967	l = −23→23
13714 measured reflections

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0388P)2 + 0.7398P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.001
1938 reflections	Δρmax = 0.32 e Å−3
129 parameters	Δρmin = −0.35 e Å−3
1 restraint	Absolute structure: Flack (1983), 862 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.28 (9)

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 > 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
C1	0.1466 (5)	0.1851 (3)	0.23620 (14)	0.0167 (5)
C2	−0.0521 (4)	0.0966 (3)	0.21287 (14)	0.0161 (5)
C3	−0.0939 (5)	0.0943 (3)	0.13814 (14)	0.0182 (5)
H3	−0.2255	0.0377	0.1201	0.022*
C4	0.0535 (5)	0.1735 (3)	0.08831 (15)	0.0175 (5)
C5	0.0162 (5)	0.1732 (3)	0.01110 (15)	0.0204 (6)
H5	−0.113	0.1173	−0.009	0.024*
C6	0.1668 (5)	0.2538 (3)	−0.03428 (14)	0.0196 (6)
H6	0.1416	0.254	−0.0859	0.024*
C7	0.3592 (5)	0.3363 (3)	−0.00485 (15)	0.0217 (6)
H7	0.4622	0.3918	−0.0371	0.026*
C8	0.4009 (5)	0.3382 (3)	0.06923 (15)	0.0200 (6)
H8	0.5315	0.3945	0.0882	0.024*
C9	0.2487 (5)	0.2563 (3)	0.11715 (13)	0.0164 (5)
C10	−0.2112 (4)	0.0090 (3)	0.26469 (13)	0.0168 (5)
N1	0.2901 (4)	0.2608 (3)	0.19237 (12)	0.0173 (5)
O1	−0.1908 (4)	0.0077 (3)	0.33080 (10)	0.0268 (5)
O2	−0.3754 (4)	−0.0713 (3)	0.22913 (11)	0.0256 (5)
H2	−0.4571	−0.1233	0.2594	0.038*
Cl1	0.22006 (13)	0.19998 (8)	0.32850 (3)	0.02526 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0190 (13)	0.0187 (13)	0.0124 (11)	0.0014 (10)	−0.0030 (9)	−0.0007 (10)
C2	0.0152 (13)	0.0183 (12)	0.0148 (13)	0.0012 (10)	0.0014 (9)	0.0008 (10)
C3	0.0137 (13)	0.0211 (13)	0.0198 (13)	−0.0030 (10)	0.0003 (11)	−0.0030 (10)
C4	0.0168 (13)	0.0180 (12)	0.0176 (12)	0.0023 (10)	0.0013 (10)	−0.0001 (10)
C5	0.0183 (14)	0.0233 (13)	0.0195 (13)	−0.0025 (11)	−0.0025 (11)	−0.0032 (11)
C6	0.0235 (17)	0.0227 (13)	0.0127 (12)	0.0034 (10)	−0.0010 (10)	−0.0001 (9)
C7	0.0221 (15)	0.0239 (14)	0.0191 (13)	−0.0008 (11)	0.0041 (11)	0.0029 (11)
C8	0.0174 (14)	0.0220 (13)	0.0208 (13)	0.0003 (11)	−0.0002 (10)	−0.0002 (11)
C9	0.0170 (14)	0.0169 (11)	0.0151 (11)	0.0006 (11)	−0.0019 (11)	−0.0008 (8)
C10	0.0142 (13)	0.0168 (12)	0.0195 (13)	−0.0022 (10)	0.0035 (10)	−0.0008 (10)
N1	0.0171 (11)	0.0176 (10)	0.0173 (10)	−0.0023 (8)	−0.0008 (9)	−0.0002 (9)
O1	0.0259 (10)	0.0380 (12)	0.0165 (9)	−0.0116 (9)	0.0015 (8)	−0.0001 (8)
O2	0.0242 (11)	0.0347 (11)	0.0180 (10)	−0.0156 (9)	0.0012 (8)	0.0041 (9)
Cl1	0.0242 (3)	0.0352 (3)	0.0164 (3)	−0.0106 (3)	−0.0016 (3)	0.0029 (2)

C1—N1	1.306 (3)	C6—C7	1.408 (4)
C1—C2	1.424 (4)	C6—H6	0.95
C1—Cl1	1.736 (3)	C7—C8	1.368 (4)
C2—C3	1.380 (4)	C7—H7	0.95
C2—C10	1.498 (3)	C8—C9	1.407 (4)
C3—C4	1.402 (4)	C8—H8	0.95
C3—H3	0.95	C9—N1	1.389 (3)
C4—C9	1.418 (4)	C10—O1	1.208 (3)
C4—C5	1.420 (4)	C10—O2	1.323 (3)
C5—C6	1.368 (4)	O2—H2	0.84
C5—H5	0.95
N1—C1—C2	124.9 (2)	C5—C6—H6	119.8
N1—C1—Cl1	113.6 (2)	C7—C6—H6	119.8
C2—C1—Cl1	121.5 (2)	C8—C7—C6	121.3 (3)
C3—C2—C1	116.3 (2)	C8—C7—H7	119.3
C3—C2—C10	120.2 (2)	C6—C7—H7	119.3
C1—C2—C10	123.5 (2)	C7—C8—C9	119.5 (3)
C2—C3—C4	121.5 (3)	C7—C8—H8	120.2
C2—C3—H3	119.3	C9—C8—H8	120.2
C4—C3—H3	119.3	N1—C9—C8	119.2 (2)
C3—C4—C9	117.8 (2)	N1—C9—C4	121.0 (2)
C3—C4—C5	123.0 (3)	C8—C9—C4	119.8 (2)
C9—C4—C5	119.2 (2)	O1—C10—O2	123.6 (2)
C6—C5—C4	119.8 (3)	O1—C10—C2	124.7 (2)
C6—C5—H5	120.1	O2—C10—C2	111.7 (2)
C4—C5—H5	120.1	C1—N1—C9	118.5 (2)
C5—C6—C7	120.3 (2)	C10—O2—H2	109.5
N1—C1—C2—C3	−0.8 (4)	C7—C8—C9—C4	−0.3 (4)
Cl1—C1—C2—C3	179.6 (2)	C3—C4—C9—N1	−1.0 (4)
N1—C1—C2—C10	179.0 (2)	C5—C4—C9—N1	179.4 (2)
Cl1—C1—C2—C10	−0.6 (4)	C3—C4—C9—C8	−179.7 (2)
C1—C2—C3—C4	0.7 (4)	C5—C4—C9—C8	0.7 (4)
C10—C2—C3—C4	−179.2 (2)	C3—C2—C10—O1	−178.2 (3)
C2—C3—C4—C9	0.2 (4)	C1—C2—C10—O1	1.9 (4)
C2—C3—C4—C5	179.8 (3)	C3—C2—C10—O2	3.3 (4)
C3—C4—C5—C6	179.7 (3)	C1—C2—C10—O2	−176.6 (2)
C9—C4—C5—C6	−0.6 (4)	C2—C1—N1—C9	0.1 (4)
C4—C5—C6—C7	0.3 (4)	Cl1—C1—N1—C9	179.68 (18)
C5—C6—C7—C8	0.1 (4)	C8—C9—N1—C1	179.6 (2)
C6—C7—C8—C9	0.0 (4)	C4—C9—N1—C1	0.9 (4)
C7—C8—C9—N1	−179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1i	0.84	1.95	2.768 (3)	164
C3—H3···O2	0.95	2.34	2.685 (4)	101
C8—H8···O1ii	0.95	2.37	3.290 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1i	0.84	1.95	2.768 (3)	164
C8—H8⋯O1ii	0.95	2.37	3.290 (4)	163

Symmetry codes: (i) ; (ii) .