Dichlorido(dimethyl-glyoximato-κN,N')(dimethyl-glyoxime-κN,N')cobalt(III).

In the title compound, [Co(C(4)H(7)N(2)O(2))Cl(2)(C(4)H(8)N(2)O(2))], the Co(III) ion has a distorted octa-hedral coordination environment. The equatorial plane consists of four N atoms, two each from the dimethyl-glyoxime and dimethyl-glyoximate ligands, while the two axial positions are occupied by two chloride ions. Strong intra-molecular O-H⋯O hydrogen bonds are observed between the dimethyl-glyoxime and dimethyl-glyoximate ligands. Mol-ecules are linked into a chain running along the [101] direction by O-H⋯O and C-H⋯Cl hydrogen bonds. The chains are cross-linked through inter-molecular C-H⋯Cl hydrogen bonds.

Related literature

For related literature, see: Dayalan & Vijayaraghavan (2001 ▶); Lee et al. (2007 ▶); Gupta et al. (2000 ▶, 2001 ▶, 2004 ▶); Ohkubo & Fukuzumi (2005 ▶); Raza­velt et al. (2005 ▶). Trommel et al. (2001 ▶).

Experimental

Crystal data

[Co(C4H7N2O2)Cl2(C4H8N2O2)]

M = 361.07

Monoclinic,

a = 8.1901 (2) Å

b = 8.1261 (2) Å

c = 10.4463 (3) Å

β = 102.007 (1)°

V = 680.03 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.67 mm−1

T = 293 (2) K

0.20 × 0.12 × 0.12 mm

Data collection

Bruker–Nonius Kappa-APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.786, T max = 0.819

10990 measured reflections

5284 independent reflections

4711 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.057

S = 0.99

5284 reflections

179 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), 2067 Friedel pairs

Flack parameter: 0.008 (7)

Data collection: APEX2 (Bruker–Nonius, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker–Nonius, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068407/ci2517sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068407/ci2517Isup2.hkl

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

[Co(C4H7N2O2)Cl2(C4H8N2O2)]	F000 = 368
Mr = 361.07	Dx = 1.763 Mg m−3
Monoclinic, Pn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 3586 reflections
a = 8.1901 (2) Å	θ = 2.8–37.2º
b = 8.1261 (2) Å	µ = 1.67 mm−1
c = 10.4463 (3) Å	T = 293 (2) K
β = 102.007 (1)º	Plate, green
V = 680.03 (3) Å3	0.20 × 0.12 × 0.12 mm
Z = 2

Bruker–Nonius Kappa APEXII CCD diffractometer	5284 independent reflections
Radiation source: fine-focus sealed tube	4711 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 293(2) K	θmax = 37.2º
ω and φ scans	θmin = 2.9º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −12→13
Tmin = 0.786, Tmax = 0.819	k = −13→13
10990 measured reflections	l = −17→17

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.025	w = 1/[σ2(Fo2) + (0.0235P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.057	(Δ/σ)max = 0.023
S = 0.99	Δρmax = 0.56 e Å−3
5284 reflections	Δρmin = −0.29 e Å−3
179 parameters	Extinction correction: none
2 restraints	Absolute structure: Flack (1983), 2067 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.008 (7)
Secondary atom site location: difference Fourier map

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
C1	0.2744 (2)	−0.2411 (2)	0.7384 (2)	0.0354 (4)
H1A	0.3762	−0.3016	0.7436	0.053*
H1B	0.1848	−0.2974	0.6812	0.053*
H1C	0.2497	−0.2325	0.8241	0.053*
C2	0.29345 (19)	−0.07336 (17)	0.68614 (15)	0.0255 (3)
C3	0.15626 (19)	0.01410 (18)	0.60187 (15)	0.0259 (3)
C4	−0.0162 (2)	−0.0517 (2)	0.56788 (19)	0.0362 (4)
H4A	−0.0912	0.0339	0.5290	0.054*
H4B	−0.0486	−0.0908	0.6457	0.054*
H4C	−0.0207	−0.1408	0.5069	0.054*
C5	0.5786 (2)	0.6808 (2)	0.5132 (2)	0.0353 (4)
H5A	0.6540	0.6827	0.4541	0.053*
H5B	0.6213	0.7497	0.5873	0.053*
H5C	0.4712	0.7208	0.4691	0.053*
C6	0.5617 (2)	0.50905 (17)	0.55842 (15)	0.0264 (3)
C7	0.70180 (19)	0.41674 (18)	0.63553 (16)	0.0266 (3)
C8	0.8762 (2)	0.4804 (2)	0.6649 (2)	0.0411 (4)
H8A	0.8866	0.5647	0.7305	0.062*
H8B	0.9027	0.5253	0.5867	0.062*
H8C	0.9518	0.3921	0.6966	0.062*
Cl1	0.36969 (5)	0.33736 (5)	0.79458 (4)	0.03361 (8)
Cl2	0.48754 (5)	0.09885 (5)	0.44061 (4)	0.03422 (9)
Co	0.42858 (2)	0.21491 (2)	0.618650 (19)	0.02055 (4)
N1	0.43373 (15)	0.00641 (15)	0.70278 (13)	0.0232 (2)
N2	0.20367 (15)	0.15171 (15)	0.56038 (12)	0.0242 (2)
N3	0.65689 (16)	0.27610 (14)	0.67399 (13)	0.0249 (2)
N4	0.42440 (16)	0.42760 (15)	0.53841 (13)	0.0257 (2)
O1	0.57344 (14)	−0.05436 (13)	0.77384 (12)	0.0303 (2)
O2	0.09198 (16)	0.24162 (15)	0.46980 (13)	0.0301 (2)
H2	0.0688	0.1904	0.4008	0.045*
O3	0.77626 (15)	0.18097 (16)	0.74654 (14)	0.0362 (3)
H3	0.7352	0.0934	0.7628	0.054*
O4	0.28559 (16)	0.50431 (15)	0.46882 (14)	0.0378 (3)
H4	0.2091	0.4377	0.4506	0.057*

	U11	U22	U33	U12	U13	U23
C1	0.0400 (9)	0.0242 (7)	0.0421 (10)	−0.0089 (7)	0.0088 (8)	0.0041 (7)
C2	0.0304 (7)	0.0209 (5)	0.0252 (7)	−0.0042 (5)	0.0061 (6)	−0.0010 (5)
C3	0.0278 (7)	0.0254 (6)	0.0247 (7)	−0.0041 (5)	0.0061 (5)	−0.0038 (5)
C4	0.0295 (8)	0.0382 (8)	0.0401 (9)	−0.0097 (7)	0.0052 (6)	−0.0017 (7)
C5	0.0420 (10)	0.0239 (6)	0.0423 (10)	−0.0035 (7)	0.0138 (8)	0.0061 (7)
C6	0.0352 (7)	0.0208 (5)	0.0250 (7)	−0.0012 (5)	0.0108 (6)	0.0010 (5)
C7	0.0266 (7)	0.0249 (6)	0.0284 (7)	−0.0044 (5)	0.0060 (6)	−0.0009 (6)
C8	0.0336 (8)	0.0405 (9)	0.0493 (11)	−0.0137 (7)	0.0085 (7)	0.0027 (8)
Cl1	0.0474 (2)	0.02841 (16)	0.02782 (18)	0.00147 (15)	0.01415 (16)	−0.00198 (14)
Cl2	0.0435 (2)	0.03213 (17)	0.02942 (18)	−0.00460 (16)	0.01298 (16)	−0.00663 (15)
Co	0.02324 (7)	0.01784 (6)	0.02009 (7)	−0.00196 (6)	0.00338 (5)	0.00024 (6)
N1	0.0265 (6)	0.0198 (5)	0.0229 (6)	−0.0016 (4)	0.0040 (4)	0.0001 (4)
N2	0.0249 (6)	0.0231 (5)	0.0229 (6)	−0.0003 (5)	0.0011 (4)	−0.0002 (5)
N3	0.0257 (5)	0.0213 (5)	0.0265 (6)	−0.0010 (4)	0.0028 (5)	0.0003 (5)
N4	0.0313 (6)	0.0225 (5)	0.0231 (6)	0.0021 (5)	0.0050 (5)	0.0031 (4)
O1	0.0290 (5)	0.0268 (5)	0.0320 (6)	0.0008 (4)	−0.0010 (4)	0.0085 (4)
O2	0.0293 (6)	0.0312 (5)	0.0260 (5)	0.0023 (4)	−0.0027 (4)	−0.0016 (4)
O3	0.0286 (6)	0.0295 (5)	0.0462 (8)	0.0009 (5)	−0.0020 (5)	0.0101 (5)
O4	0.0339 (6)	0.0338 (6)	0.0420 (7)	0.0040 (5)	−0.0002 (5)	0.0115 (6)

C1—C2	1.489 (2)	C7—C8	1.490 (2)
C1—H1A	0.96	C8—H8A	0.96
C1—H1B	0.96	C8—H8B	0.96
C1—H1C	0.96	C8—H8C	0.96
C2—N1	1.2990 (19)	Cl1—Co	2.2292 (4)
C2—C3	1.460 (2)	Cl2—Co	2.2261 (4)
C3—N2	1.2881 (18)	Co—N2	1.8870 (12)
C3—C4	1.483 (2)	Co—N3	1.9048 (13)
C4—H4A	0.96	Co—N1	1.9051 (12)
C4—H4B	0.96	Co—N4	1.9181 (12)
C4—H4C	0.96	N1—O1	1.3231 (17)
C5—C6	1.489 (2)	N1—O1	1.3231 (17)
C5—H5A	0.96	N2—O2	1.3805 (17)
C5—H5B	0.96	N3—O3	1.3489 (17)
C5—H5C	0.96	N4—O4	1.3659 (17)
C6—N4	1.284 (2)	O2—H2	0.82
C6—C7	1.464 (2)	O3—H3	0.82
C7—N3	1.2901 (18)	O4—H4	0.82
C2—C1—H1A	109.5	H8A—C8—H8C	109.5
C2—C1—H1B	109.5	H8B—C8—H8C	109.5
H1A—C1—H1B	109.5	N2—Co—N3	178.64 (6)
C2—C1—H1C	109.5	N2—Co—N1	80.40 (5)
H1A—C1—H1C	109.5	N3—Co—N1	99.56 (5)
H1B—C1—H1C	109.5	N2—Co—N4	100.18 (5)
N1—C2—C3	112.72 (13)	N3—Co—N4	79.90 (5)
N1—C2—C1	124.42 (15)	N1—Co—N4	178.48 (6)
C3—C2—C1	122.72 (13)	N2—Co—Cl2	88.97 (4)
N2—C3—C2	112.18 (13)	N3—Co—Cl2	89.67 (4)
N2—C3—C4	124.84 (15)	N1—Co—Cl2	91.19 (4)
C2—C3—C4	122.98 (13)	N4—Co—Cl2	90.23 (4)
C3—C4—H4A	109.5	N2—Co—Cl1	91.34 (4)
C3—C4—H4B	109.5	N3—Co—Cl1	90.02 (4)
H4A—C4—H4B	109.5	N1—Co—Cl1	90.26 (4)
C3—C4—H4C	109.5	N4—Co—Cl1	88.33 (4)
H4A—C4—H4C	109.5	Cl2—Co—Cl1	178.550 (17)
H4B—C4—H4C	109.5	C2—N1—O1	121.76 (12)
C6—C5—H5A	109.5	C2—N1—O1	121.76 (12)
C6—C5—H5B	109.5	C2—N1—Co	116.61 (11)
H5A—C5—H5B	109.5	O1—N1—Co	121.62 (9)
C6—C5—H5C	109.5	O1—N1—Co	121.62 (9)
H5A—C5—H5C	109.5	C3—N2—O2	119.14 (12)
H5B—C5—H5C	109.5	C3—N2—Co	118.04 (11)
N4—C6—C7	112.65 (13)	O2—N2—Co	122.70 (9)
N4—C6—C5	124.55 (16)	C7—N3—O3	117.54 (13)
C7—C6—C5	122.77 (14)	C7—N3—Co	117.53 (11)
N3—C7—C6	112.57 (13)	O3—N3—Co	124.89 (9)
N3—C7—C8	124.50 (15)	C6—N4—O4	117.09 (12)
C6—C7—C8	122.93 (14)	C6—N4—Co	117.25 (11)
C7—C8—H8A	109.5	O4—N4—Co	125.52 (9)
C7—C8—H8B	109.5	N2—O2—H2	109.5
H8A—C8—H8B	109.5	N3—O3—H3	109.5
C7—C8—H8C	109.5	N4—O4—H4	109.5
N1—C2—C3—N2	0.71 (19)	N4—Co—N2—C3	−176.40 (11)
C1—C2—C3—N2	−175.17 (14)	Cl2—Co—N2—C3	93.56 (11)
N1—C2—C3—C4	179.90 (14)	Cl1—Co—N2—C3	−87.86 (11)
C1—C2—C3—C4	4.0 (2)	N1—Co—N2—O2	−173.82 (12)
N4—C6—C7—N3	−3.70 (19)	N4—Co—N2—O2	7.61 (12)
C5—C6—C7—N3	174.29 (15)	Cl2—Co—N2—O2	−82.44 (11)
N4—C6—C7—C8	176.17 (15)	Cl1—Co—N2—O2	96.15 (11)
C5—C6—C7—C8	−5.8 (2)	C6—C7—N3—O3	−179.68 (13)
C3—C2—N1—O1	−178.56 (13)	C8—C7—N3—O3	0.5 (2)
C1—C2—N1—O1	−2.8 (2)	C6—C7—N3—Co	2.60 (17)
C3—C2—N1—O1	−178.56 (13)	C8—C7—N3—Co	−177.27 (13)
C1—C2—N1—O1	−2.8 (2)	N1—Co—N3—C7	−179.35 (11)
C3—C2—N1—Co	1.02 (16)	N4—Co—N3—C7	−0.79 (11)
C1—C2—N1—Co	176.83 (13)	Cl2—Co—N3—C7	89.50 (11)
N2—Co—N1—C2	−1.70 (11)	Cl1—Co—N3—C7	−89.08 (11)
N3—Co—N1—C2	179.68 (11)	N1—Co—N3—O3	3.11 (13)
Cl2—Co—N1—C2	−90.45 (11)	N4—Co—N3—O3	−178.33 (13)
Cl1—Co—N1—C2	89.61 (10)	Cl2—Co—N3—O3	−88.04 (12)
N2—Co—N1—O1	177.89 (12)	Cl1—Co—N3—O3	93.37 (12)
N3—Co—N1—O1	−0.74 (12)	C7—C6—N4—O4	179.09 (13)
Cl2—Co—N1—O1	89.14 (11)	C5—C6—N4—O4	1.1 (2)
Cl1—Co—N1—O1	−90.80 (11)	C7—C6—N4—Co	3.19 (17)
N2—Co—N1—O1	177.89 (12)	C5—C6—N4—Co	−174.76 (13)
N3—Co—N1—O1	−0.74 (12)	N2—Co—N4—C6	179.87 (11)
Cl2—Co—N1—O1	89.14 (11)	N3—Co—N4—C6	−1.51 (11)
Cl1—Co—N1—O1	−90.80 (11)	Cl2—Co—N4—C6	−91.14 (11)
C2—C3—N2—O2	173.96 (13)	Cl1—Co—N4—C6	88.81 (11)
C4—C3—N2—O2	−5.2 (2)	N2—Co—N4—O4	4.35 (13)
C2—C3—N2—Co	−2.17 (17)	N3—Co—N4—O4	−177.02 (13)
C4—C3—N2—Co	178.66 (12)	Cl2—Co—N4—O4	93.35 (12)
N1—Co—N2—C3	2.17 (11)	Cl1—Co—N4—O4	−86.70 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.82	1.81	2.5875 (16)	158
O4—H4···O2	0.82	1.89	2.6604 (18)	156
O2—H2···O1i	0.82	1.73	2.5297 (17)	163
C4—H4C···Cl1i	0.96	2.73	3.6473 (19)	160
C5—H5A···Cl1ii	0.96	2.67	3.6317 (18)	175

Table 1

Selected bond lengths (Å)

Cl1—Co	2.2292 (4)
Cl2—Co	2.2261 (4)
Co—N2	1.8870 (12)
Co—N3	1.9048 (13)
Co—N1	1.9051 (12)
Co—N4	1.9181 (12)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1	0.82	1.81	2.5875 (16)	158
O4—H4⋯O2	0.82	1.89	2.6604 (18)	156
O2—H2⋯O1i	0.82	1.73	2.5297 (17)	163
C4—H4C⋯Cl1i	0.96	2.73	3.6473 (19)	160
C5—H5A⋯Cl1ii	0.96	2.67	3.6317 (18)	175

Symmetry codes: (i) ; (ii) .