Dichlorido(dimethyl­glyoximato-κ2N,N′)(dimethyl­glyoxime-κ2N,N′)cobalt(III)

Ramesh, P.; SubbiahPandi, A.; Jothi, P.; Revathi, C.; Dayalan, A.

doi:10.1107/S1600536807068407

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages m300-m301

doi:10.1107/S1600536807068407

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Dichlorido(dimethylglyoximato-κ²N,N′)(dimethylglyoxime-κ²N,N′)cobalt(III)

P. Ramesh,^a A. SubbiahPandi,^a ^* P. Jothi,^b C. Revathi ^b and A. Dayalan ^b

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Chemistry, Loyola College (Autonomous), Chennai 600 034, India
^*Correspondence e-mail: a_spandian@yahoo.com

(Received 10 November 2007; accepted 25 December 2007; online 4 January 2008)

In the title compound, [Co(C₄H₇N₂O₂)Cl₂(C₄H₈N₂O₂)], the Co^III ion has a distorted octahedral coordination environment. The equatorial plane consists of four N atoms, two each from the dimethylglyoxime and dimethylglyoximate ligands, while the two axial positions are occupied by two chloride ions. Strong intramolecular O—H⋯O hydrogen bonds are observed between the dimethylglyoxime and dimethylglyoximate ligands. Molecules 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 intermolecular 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_r = 361.07
Monoclinic, P n
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[F² > 2σ(F²)] = 0.025
wR(F²) = 0.057
S = 0.99
5284 reflections
179 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 2067 Friedel pairs
Flack parameter: 0.008 (7)

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) $[x-{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

Dimethylglyoximatocobalt(III) complexes, generally known as cobaloximes, have been studied extensively as model compounds for vitamine-B₁₂ (Trommel et al., 2001; Ohkubo & Fukuzumi, 2005). Most of the work on cobaloximes include electron-transfer reactions (Dayalan & Vijayaraghavan, 2001) and catalytic activity (Razavelt et al., 2005) in solution. There are few literature evidences relating the structural aspects of cobaloximes (Gupta et al., 2000; Gupta et al., 2001; Gupta et al., 2004). We report here the synthesis and X-ray crystal structure of the title compoud.

The coordination geometry around the Co^III ion can be described as a slightly distorted octahedron. The axial positions are occupied by the chloride ions. The glyoxime moieties are individually planar. The Co^III ion and the four N atoms of dimethylglyoxime ligands are approximately coplanar. The Co—N and Co—Cl bond lengths are normal (Table 1), and are comparable with the corresponding values observed in a related complex (Lee et al., 2007).

Strong intramolecular O—H···O hydrogen bonds are observed between the dimethylglyoxime and dimethylglyoximate ligands (Table 2). The crystal packing is stabilized by O—H···O and C—H···Cl hydrogen bonds. Atoms O2 and C4 of the molecule at (x, y, z) act as donors to atoms O1 and Cl1, respectively, of the molecule at (-1/2 + x, -y, -1/2 + z). These two hydrogen bonds form a chain running along the [1 0 1] direction. The chains are cross-linked through C—H···Cl intermolecular hydrogen bonds.

Related literature top

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 top

Cobalt(II) chloride hexahydrate was thoroughly grinded and exposed to microwave for 30 s. Dehydrated cobalt(II) chloride (1.3 g) was mixed with dimethyl glyoxime (2.32 g). The mixture was intimately grinded and made into a paste using acetone and exposed to microwave radiation for 60 s. The microwave treated reaction mixture was exposed to atmosphere, till it became green. The green coloured product was recrystallized from acetone. Single crystals were obtained by slow evaporation of the acetone solution.

Computing details top

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: APEX2 (Bruker–Nonius, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. The structure of the title complex. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitary radii.

Dichlorido(dimethylglyoximato-κ²N,N')(dimethylglyoxime- κ²N,N')cobalt(III) top

Crystal data top

[Co(C₄H₇N₂O₂)Cl₂(C₄H₈N₂O₂)]	F(000) = 368
M_r = 361.07	D_x = 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 = 2.8–37.2°
b = 8.1261 (2) Å	µ = 1.67 mm⁻¹
c = 10.4463 (3) Å	T = 293 K
β = 102.007 (1)°	Plate, green
V = 680.03 (3) Å³	0.20 × 0.12 × 0.12 mm
Z = 2

Data collection top

Bruker–Nonius Kappa APEXII CCD diffractometer	5284 independent reflections
Radiation source: fine-focus sealed tube	4711 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω and ϕ scans	θ_max = 37.2°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −12→13
T_min = 0.786, T_max = 0.819	k = −13→13
10990 measured reflections	l = −17→17

Refinement top

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)] = 0.025	H-atom parameters constrained
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0235P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.023
5284 reflections	Δρ_max = 0.56 e Å⁻³
179 parameters	Δρ_min = −0.29 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2067 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.008 (7)

Crystal data top

[Co(C₄H₇N₂O₂)Cl₂(C₄H₈N₂O₂)]	V = 680.03 (3) Å³
M_r = 361.07	Z = 2
Monoclinic, Pn	Mo Kα radiation
a = 8.1901 (2) Å	µ = 1.67 mm⁻¹
b = 8.1261 (2) Å	T = 293 K
c = 10.4463 (3) Å	0.20 × 0.12 × 0.12 mm
β = 102.007 (1)°

Data collection top

Bruker–Nonius Kappa APEXII CCD diffractometer	5284 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	4711 reflections with I > 2σ(I)
T_min = 0.786, T_max = 0.819	R_int = 0.021
10990 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.057	Δρ_max = 0.56 e Å⁻³
S = 0.99	Δρ_min = −0.29 e Å⁻³
5284 reflections	Absolute structure: Flack (1983), 2067 Friedel pairs
179 parameters	Absolute structure parameter: 0.008 (7)
2 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y, z−1/2; (ii) x+1/2, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₄H₇N₂O₂)Cl₂(C₄H₈N₂O₂)]
M_r	361.07
Crystal system, space group	Monoclinic, Pn
Temperature (K)	293
a, b, c (Å)	8.1901 (2), 8.1261 (2), 10.4463 (3)
β (°)	102.007 (1)
V (Å³)	680.03 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.67
Crystal size (mm)	0.20 × 0.12 × 0.12

Data collection
Diffractometer	Bruker–Nonius Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.786, 0.819
No. of measured, independent and observed [I > 2σ(I)] reflections	10990, 5284, 4711
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.851

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.057, 0.99
No. of reflections	5284
No. of parameters	179
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.29
Absolute structure	Flack (1983), 2067 Friedel pairs
Absolute structure parameter	0.008 (7)

Computer programs: APEX2 (Bruker–Nonius, 2004), SAINT (Bruker–Nonius, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y, z−1/2; (ii) x+1/2, −y+1, z−1/2.

Acknowledgements

The authors are grateful to Dr S. Ramanathan, Principal, Presidency College (Autonomous), Chennai, India, and Rev. Fr A. Albert Muthumalai, S. J., Principal, Loyola College (Autonomous), Chennai, India, for providing the necessary facilities. The Head, SAIF, CDRI, Lucknow, India, is thanked for supplying the elemental analysis data and the Head, SAIF, IIT Madras, Chennai, India, for recording the NMR spectra and for the X-ray data collection.

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