catena-Poly[cobalt(II)-bis-(μ-3,7-dichloro-quinoline-8-carboxyl-ato-κN,O:O')].

In the crystal structure of the title compound, [Co(C(10)H(4)Cl(2)NO(2))(2)](n), the Co(II) cation lies on a twofold rotation axis. Each cation is N,O-chelated by the carboxyl-ate anions of two 3,7-dichloro-quinoline-8-carboxyl-ate ligands. The second carboxyl-ate O atom of each ligand coordinates to the Co(II) cation of an adjacent mol-ecule, linking the cations into a linear chain. Strong inter-chain π-π stacking inter-actions are observed in the crystal structure (perpendicular distance 3.42 Å, centroid-to-centroid distance 3.874 Å).

Related literature

For the use of 3,7-dichloro-8-quinoline­carboxylic acid as a herbicide, see: Nuria et al. (1997 ▶); Pornprom et al. (2006 ▶); Sunohara & Matsumoto (2004 ▶); Tresch & Grossmann (2002 ▶). For related vanadium and cadmium complexes, see Chen et al. (2001 ▶); Yang et al. (2005 ▶). For related literature, see: Turel et al. (2004 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

[Co(C10H4Cl2NO2)2]

M = 541.01

Orthorhombic,

a = 13.5109 (14) Å

b = 15.964 (2) Å

c = 9.2157 (16) Å

V = 1987.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.43 mm−1

T = 298 (2) K

0.49 × 0.33 × 0.31 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.57, T max = 0.64

9558 measured reflections

1752 independent reflections

1404 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.089

S = 1.11

1752 reflections

141 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.76 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066755/sj2456sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066755/sj2456Isup2.hkl

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

[Co(C10H4Cl2NO2)2]	F000 = 1076
Mr = 541.01	Dx = 1.808 Mg m−3Dm = 1.800 Mg m−3Dm measured by not measured
Orthorhombic, Pccn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 9558 reflections
a = 13.5109 (14) Å	θ = 2.0–25.0º
b = 15.964 (2) Å	µ = 1.43 mm−1
c = 9.2157 (16) Å	T = 298 (2) K
V = 1987.7 (5) Å3	Block, red
Z = 4	0.49 × 0.33 × 0.31 mm

Siemens SMART CCD area-detector diffractometer	1752 independent reflections
Radiation source: fine-focus sealed tube	1404 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −16→13
Tmin = 0.57, Tmax = 0.64	k = −18→18
9558 measured reflections	l = −10→9

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0291P)2 + 3.6236P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
1752 reflections	Δρmax = 0.67 e Å−3
141 parameters	Δρmin = −0.76 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Co1	0.7500	0.7500	0.25905 (6)	0.02337 (17)
Cl1	0.77826 (7)	0.45967 (6)	−0.08682 (10)	0.0438 (3)
Cl2	1.11100 (8)	0.71113 (7)	0.54570 (14)	0.0641 (4)
N1	0.89374 (19)	0.68581 (16)	0.2651 (3)	0.0271 (6)
O1	0.70392 (16)	0.66997 (13)	0.0924 (2)	0.0296 (5)
O2	0.80139 (16)	0.65857 (13)	−0.1029 (2)	0.0287 (5)
C1	0.7764 (2)	0.64027 (19)	0.0240 (3)	0.0253 (7)
C2	0.8430 (2)	0.57762 (19)	0.0989 (3)	0.0254 (7)
C3	0.8519 (2)	0.4963 (2)	0.0541 (4)	0.0305 (7)
C4	0.9198 (3)	0.4403 (2)	0.1170 (4)	0.0406 (9)
H4	0.9214	0.3846	0.0871	0.049*
C5	0.9831 (3)	0.4674 (2)	0.2212 (4)	0.0405 (9)
H5	1.0300	0.4309	0.2594	0.049*
C6	0.9783 (2)	0.5510 (2)	0.2723 (4)	0.0325 (8)
C7	0.9051 (2)	0.60506 (19)	0.2140 (3)	0.0273 (7)
C8	0.9570 (2)	0.7133 (2)	0.3621 (4)	0.0325 (8)
H8	0.9503	0.7681	0.3949	0.039*
C9	1.0338 (2)	0.6646 (2)	0.4188 (4)	0.0378 (8)
C10	1.0438 (3)	0.5835 (2)	0.3773 (4)	0.0397 (9)
H10	1.0929	0.5499	0.4175	0.048*

	U11	U22	U33	U12	U13	U23
Co1	0.0269 (3)	0.0247 (3)	0.0185 (3)	0.0027 (3)	0.000	0.000
Cl1	0.0472 (5)	0.0369 (5)	0.0472 (6)	−0.0042 (4)	−0.0028 (4)	−0.0106 (4)
Cl2	0.0561 (6)	0.0563 (7)	0.0799 (8)	0.0064 (5)	−0.0383 (6)	−0.0098 (6)
N1	0.0271 (14)	0.0274 (14)	0.0268 (15)	0.0037 (11)	−0.0010 (11)	0.0010 (11)
O1	0.0316 (12)	0.0338 (12)	0.0233 (12)	0.0062 (10)	−0.0014 (10)	−0.0035 (10)
O2	0.0344 (12)	0.0307 (12)	0.0211 (12)	0.0016 (10)	0.0015 (9)	0.0020 (10)
C1	0.0322 (17)	0.0217 (15)	0.0220 (16)	−0.0028 (12)	−0.0030 (13)	0.0000 (12)
C2	0.0258 (16)	0.0285 (16)	0.0218 (16)	0.0024 (13)	0.0053 (13)	0.0052 (13)
C3	0.0331 (17)	0.0261 (17)	0.0323 (18)	−0.0021 (14)	0.0046 (14)	0.0002 (14)
C4	0.051 (2)	0.0242 (18)	0.047 (2)	0.0059 (16)	0.0032 (19)	−0.0001 (16)
C5	0.042 (2)	0.0340 (19)	0.045 (2)	0.0122 (16)	−0.0004 (17)	0.0073 (17)
C6	0.0332 (18)	0.0330 (18)	0.0311 (19)	0.0051 (14)	0.0012 (14)	0.0049 (15)
C7	0.0266 (16)	0.0289 (17)	0.0264 (17)	0.0044 (13)	0.0070 (13)	0.0044 (14)
C8	0.0292 (17)	0.0315 (18)	0.037 (2)	0.0018 (14)	−0.0010 (15)	0.0008 (15)
C9	0.0306 (18)	0.042 (2)	0.041 (2)	0.0018 (15)	−0.0088 (16)	−0.0023 (17)
C10	0.0337 (19)	0.045 (2)	0.040 (2)	0.0106 (16)	−0.0065 (16)	0.0053 (18)

Co1—O1	2.093 (2)	C2—C3	1.368 (4)
Co1—O1i	2.093 (2)	C2—C7	1.422 (4)
Co1—O2ii	2.057 (2)	C3—C4	1.406 (5)
Co1—O2iii	2.057 (2)	C4—C5	1.357 (5)
Co1—N1i	2.197 (2)	C4—H4	0.9300
Co1—N1	2.197 (2)	C5—C6	1.416 (5)
Cl1—C3	1.738 (3)	C5—H5	0.9300
Cl2—C9	1.734 (4)	C6—C10	1.410 (5)
N1—C8	1.312 (4)	C6—C7	1.419 (4)
N1—C7	1.381 (4)	C8—C9	1.398 (5)
O1—C1	1.257 (4)	C8—H8	0.9300
O2—C1	1.252 (4)	C9—C10	1.358 (5)
O2—Co1iv	2.057 (2)	C10—H10	0.9300
C1—C2	1.512 (4)
O2ii—Co1—O2iii	103.60 (12)	C7—C2—C1	119.2 (3)
O2ii—Co1—O1	170.96 (9)	C2—C3—C4	122.5 (3)
O2iii—Co1—O1	85.43 (8)	C2—C3—Cl1	119.6 (3)
O2ii—Co1—O1i	85.43 (8)	C4—C3—Cl1	117.9 (3)
O2iii—Co1—O1i	170.96 (8)	C5—C4—C3	120.0 (3)
O1—Co1—O1i	85.55 (12)	C5—C4—H4	120.0
O2ii—Co1—N1i	87.24 (9)	C3—C4—H4	120.0
O2iii—Co1—N1i	90.97 (9)	C4—C5—C6	120.5 (3)
O1—Co1—N1i	92.31 (9)	C4—C5—H5	119.8
O1i—Co1—N1i	89.82 (9)	C6—C5—H5	119.8
O2ii—Co1—N1	90.97 (9)	C10—C6—C5	123.1 (3)
O2iii—Co1—N1	87.24 (9)	C10—C6—C7	118.3 (3)
O1—Co1—N1	89.82 (9)	C5—C6—C7	118.6 (3)
O1i—Co1—N1	92.31 (9)	N1—C7—C6	121.1 (3)
N1i—Co1—N1	177.10 (14)	N1—C7—C2	118.5 (3)
C8—N1—C7	118.2 (3)	C6—C7—C2	120.5 (3)
C8—N1—Co1	115.9 (2)	N1—C8—C9	123.5 (3)
C7—N1—Co1	121.7 (2)	N1—C8—H8	118.2
C1—O1—Co1	111.49 (19)	C9—C8—H8	118.2
C1—O2—Co1iv	130.7 (2)	C10—C9—C8	119.9 (3)
O2—C1—O1	126.2 (3)	C10—C9—Cl2	122.6 (3)
O2—C1—C2	114.9 (3)	C8—C9—Cl2	117.4 (3)
O1—C1—C2	119.0 (3)	C9—C10—C6	118.8 (3)
C3—C2—C7	117.8 (3)	C9—C10—H10	120.6
C3—C2—C1	122.9 (3)	C6—C10—H10	120.6
O2ii—Co1—N1—C8	9.9 (2)	Cl1—C3—C4—C5	176.0 (3)
O2iii—Co1—N1—C8	−93.6 (2)	C3—C4—C5—C6	3.0 (5)
O1—Co1—N1—C8	−179.1 (2)	C4—C5—C6—C10	−178.1 (4)
O1i—Co1—N1—C8	95.4 (2)	C4—C5—C6—C7	1.0 (5)
O2ii—Co1—N1—C7	166.4 (2)	C8—N1—C7—C6	4.7 (4)
O2iii—Co1—N1—C7	62.8 (2)	Co1—N1—C7—C6	−151.2 (2)
O1—Co1—N1—C7	−22.7 (2)	C8—N1—C7—C2	−174.0 (3)
O1i—Co1—N1—C7	−108.2 (2)	Co1—N1—C7—C2	30.1 (4)
O1i—Co1—O1—C1	68.44 (19)	C10—C6—C7—N1	−4.1 (5)
N1i—Co1—O1—C1	158.1 (2)	C5—C6—C7—N1	176.6 (3)
N1—Co1—O1—C1	−23.9 (2)	C10—C6—C7—C2	174.5 (3)
Co1iv—O2—C1—O1	8.1 (5)	C5—C6—C7—C2	−4.8 (5)
Co1iv—O2—C1—C2	−170.54 (19)	C3—C2—C7—N1	−177.0 (3)
Co1—O1—C1—O2	−109.2 (3)	C1—C2—C7—N1	7.7 (4)
Co1—O1—C1—C2	69.4 (3)	C3—C2—C7—C6	4.4 (4)
O2—C1—C2—C3	−65.8 (4)	C1—C2—C7—C6	−170.9 (3)
O1—C1—C2—C3	115.4 (3)	C7—N1—C8—C9	−1.4 (5)
O2—C1—C2—C7	109.2 (3)	Co1—N1—C8—C9	155.8 (3)
O1—C1—C2—C7	−69.6 (4)	N1—C8—C9—C10	−2.3 (6)
C7—C2—C3—C4	−0.3 (5)	N1—C8—C9—Cl2	179.7 (3)
C1—C2—C3—C4	174.8 (3)	C8—C9—C10—C6	2.8 (6)
C7—C2—C3—Cl1	−179.7 (2)	Cl2—C9—C10—C6	−179.4 (3)
C1—C2—C3—Cl1	−4.6 (4)	C5—C6—C10—C9	179.5 (4)
C2—C3—C4—C5	−3.4 (5)	C7—C6—C10—C9	0.4 (5)

Co1—O1	2.093 (2)
Co1—O2i	2.057 (2)
Co1—N1	2.197 (2)

O2i—Co1—O2ii	103.60 (12)
O2i—Co1—O1	170.96 (9)
O2ii—Co1—O1	85.43 (8)
O1—Co1—O1iii	85.55 (12)
O2i—Co1—N1	90.97 (9)
O2ii—Co1—N1	87.24 (9)
O1—Co1—N1	89.82 (9)
O1iii—Co1—N1	92.31 (9)
N1iii—Co1—N1	177.10 (14)

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