Bis{2-[3-(dimethyl­amino)propyl­imino­meth­yl]-4,6-disulfanylphenolato}cobalt(II)

Li, H.-Y.; Wang, L.-J.; Wang, Q.; Zeng, Q.-F.

doi:10.1107/S1600536809031389

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1073

doi:10.1107/S1600536809031389

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Bis{2-[3-(dimethylamino)propyliminomethyl]-4,6-disulfanylphenolato}cobalt(II)

Hai-Yan Li,^a Li-Jun Wang,^a Qiang Wang ^a and Qing-Fu Zeng ^a ^*

^aEngineering Research Center for Clean Production of Textile Dyeing and Printing, Ministry of Education, Wuhan 430073, People's Republic of China
^*Correspondence e-mail: qfzeng@wuse.edu.cn

(Received 31 July 2009; accepted 9 August 2009; online 15 August 2009)

In the title mononuclear complex, [Co(C₁₂H₁₇N₂OS₂)₂], the Co^II atom is four-coordinated by two N,O-bidentate Schiff base ligands, resulting in a slightly distorted trans-CoN₂O₂ square-planar coordination.

Related literature

For background to Schiff bases, see: Shi et al. (2008 ); Xu et al. (2009 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Co(C₁₂H₁₇N₂OS₂)₂]
M_r = 597.72
Triclinic, $[P \overline 1]$
a = 9.4100 (18) Å
b = 12.5482 (18) Å
c = 12.6032 (18) Å
α = 103.272 (8)°
β = 110.910 (8)°
γ = 90.612 (8)°
V = 1346.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 296 K
0.40 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.696, T_max = 0.758
7433 measured reflections
5221 independent reflections
3718 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.129
S = 1.02
5221 reflections
324 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O2	1.922 (2)
Co1—O1	1.925 (2)
Co1—N1	2.003 (3)
Co1—N3	2.011 (2)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031389/hb5029sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031389/hb5029Isup2.hkl

checkCIF report

Comment top

There has been much research interest in Schiff base metal complexes due to their molecular architectures and biological activities (Shi et al., 2008; Xu et al., 2009). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The Co(II) is four-coordinated in a slight distort square-planar configuration by two N atoms and two O atoms of the Schiff base ligand.

Related literature top

For background to Schiff bases, see: Shi et al. (2008); Xu et al. (2009). For reference structural data, see: Allen et al. (1987).

Experimental top

A mixture of 2-hydroxy-3,5-disulfanylbenzaldehyde (372 mg, 2 mmol), N,N-dimethylpropane-1,3-diamine (204 mg, 2 mmol) and CoCl₂.6H₂O (1 mmol, 238 mg) was stirred in methanol (10 ml) for 1 h. After keeping the filtrate in air for 7 d, red block-shaped crystals of (I) were formed.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of showing 30% probability displacement ellipsoids.

Bis{2-[3-(dimethylamino)propyliminomethyl]-4,6-disulfanylphenolato}cobalt(II) top

Crystal data top

[Co(C₁₂H₁₇N₂OS₂)₂]	Z = 2
M_r = 597.72	F(000) = 626
Triclinic, P1	D_x = 1.475 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4100 (18) Å	Cell parameters from 25 reflections
b = 12.5482 (18) Å	θ = 9–12°
c = 12.6032 (18) Å	µ = 0.98 mm⁻¹
α = 103.272 (8)°	T = 296 K
β = 110.910 (8)°	Block, red
γ = 90.612 (8)°	0.40 × 0.30 × 0.30 mm
V = 1346.0 (4) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	5221 independent reflections
Radiation source: fine-focus sealed tube	3718 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω/2θ scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: ψ scan (North et al., 1968)	h = −11→9
T_min = 0.696, T_max = 0.758	k = −15→15
7433 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0746P)² + 0.0983P] where P = (F_o² + 2F_c²)/3
5221 reflections	(Δ/σ)_max = 0.044
324 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Co(C₁₂H₁₇N₂OS₂)₂]	γ = 90.612 (8)°
M_r = 597.72	V = 1346.0 (4) Å³
Triclinic, P1	Z = 2
a = 9.4100 (18) Å	Mo Kα radiation
b = 12.5482 (18) Å	µ = 0.98 mm⁻¹
c = 12.6032 (18) Å	T = 296 K
α = 103.272 (8)°	0.40 × 0.30 × 0.30 mm
β = 110.910 (8)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	5221 independent reflections
Absorption correction: ψ scan (North et al., 1968)	3718 reflections with I > 2σ(I)
T_min = 0.696, T_max = 0.758	R_int = 0.022
7433 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.02	Δρ_max = 0.43 e Å⁻³
5221 reflections	Δρ_min = −0.58 e Å⁻³
324 parameters

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	1.0983 (4)	0.3759 (3)	0.4418 (3)	0.0477 (8)
C2	0.9888 (4)	0.2914 (3)	0.4161 (3)	0.0476 (8)
H2	1.0080	0.2395	0.4604	0.057*
C3	0.8478 (4)	0.2825 (3)	0.3235 (3)	0.0425 (7)
C4	0.8150 (3)	0.3595 (2)	0.2533 (3)	0.0381 (7)
C5	0.9338 (3)	0.4458 (3)	0.2854 (3)	0.0425 (7)
C6	1.0703 (4)	0.4550 (3)	0.3766 (3)	0.0476 (8)
H6	1.1439	0.5133	0.3952	0.057*
C7	0.7338 (4)	0.1967 (3)	0.3078 (3)	0.0481 (8)
H7	0.7579	0.1559	0.3637	0.058*
C8	0.4970 (4)	0.0922 (3)	0.2368 (3)	0.0589 (10)
H8A	0.5537	0.0514	0.2923	0.071*
H8B	0.4444	0.0402	0.1617	0.071*
C9	0.3798 (5)	0.1534 (4)	0.2797 (4)	0.0736 (12)
H9A	0.3209	0.1008	0.2975	0.088*
H9B	0.4353	0.2075	0.3526	0.088*
C10	0.2674 (4)	0.2124 (3)	0.1965 (4)	0.0615 (10)
H10A	0.2108	0.1588	0.1235	0.074*
H10B	0.1945	0.2418	0.2310	0.074*
C11	0.4185 (5)	0.3916 (3)	0.2747 (4)	0.0718 (12)
H11A	0.4459	0.4545	0.2522	0.108*
H11B	0.5092	0.3668	0.3234	0.108*
H11C	0.3523	0.4114	0.3175	0.108*
C12	0.2176 (4)	0.3474 (3)	0.0846 (4)	0.0714 (12)
H12A	0.1471	0.3782	0.1197	0.107*
H12B	0.1642	0.2892	0.0163	0.107*
H12C	0.2623	0.4036	0.0624	0.107*
C13	0.2718 (3)	0.0922 (2)	−0.0969 (3)	0.0392 (7)
C14	0.1551 (4)	0.0039 (3)	−0.1298 (3)	0.0444 (8)
C15	0.0298 (4)	−0.0161 (3)	−0.2317 (3)	0.0491 (8)
H15	−0.0441	−0.0741	−0.2496	0.059*
C16	0.0137 (4)	0.0506 (3)	−0.3085 (3)	0.0473 (8)
C17	0.1211 (4)	0.1372 (3)	−0.2818 (3)	0.0468 (8)
H17	0.1089	0.1814	−0.3338	0.056*
C18	0.2487 (3)	0.1596 (3)	−0.1770 (3)	0.0402 (7)
C19	0.3602 (4)	0.2499 (3)	−0.1558 (3)	0.0410 (7)
H19	0.3446	0.2842	−0.2165	0.049*
C20	0.5820 (4)	0.3734 (2)	−0.0702 (3)	0.0426 (8)
H20A	0.6134	0.4327	0.0007	0.051*
H20B	0.5278	0.4038	−0.1360	0.051*
C21	0.7228 (4)	0.3244 (3)	−0.0862 (3)	0.0492 (8)
H21A	0.7857	0.3812	−0.0948	0.059*
H21B	0.7822	0.3021	−0.0158	0.059*
C22	0.6870 (4)	0.2261 (3)	−0.1911 (3)	0.0518 (9)
H22A	0.7819	0.2021	−0.1975	0.062*
H22B	0.6342	0.1659	−0.1788	0.062*
C23	0.5051 (5)	0.1534 (3)	−0.3889 (4)	0.0679 (11)
H23A	0.4458	0.1732	−0.4598	0.102*
H23B	0.4381	0.1203	−0.3605	0.102*
H23C	0.5744	0.1020	−0.4044	0.102*
C24	0.6821 (5)	0.3107 (3)	−0.3452 (4)	0.0685 (11)
H24A	0.7578	0.2658	−0.3609	0.103*
H24B	0.7318	0.3779	−0.2880	0.103*
H24C	0.6164	0.3272	−0.4163	0.103*
Co1	0.52925 (4)	0.23544 (3)	0.08521 (3)	0.03191 (14)
N1	0.6028 (3)	0.1710 (2)	0.2245 (2)	0.0474 (7)
N2	0.3391 (3)	0.3031 (2)	0.1696 (3)	0.0528 (7)
N3	0.4787 (3)	0.2878 (2)	−0.0621 (2)	0.0394 (6)
N4	0.5922 (3)	0.2520 (2)	−0.3004 (2)	0.0474 (7)
O1	0.6877 (2)	0.35591 (18)	0.16610 (19)	0.0471 (5)
O2	0.3892 (2)	0.10552 (17)	−0.00081 (19)	0.0468 (5)
S1	0.90029 (11)	0.54412 (8)	0.20420 (9)	0.0586 (3)
H1	0.8663	0.4994	0.1023	0.088*
S2	1.27446 (11)	0.38591 (10)	0.55553 (9)	0.0675 (3)
H2A	1.2950	0.2982	0.5781	0.101*
S3	0.17582 (12)	−0.08143 (8)	−0.03595 (9)	0.0622 (3)
H3	0.2279	−0.0276	0.0638	0.093*
S4	−0.14439 (11)	0.02070 (9)	−0.43967 (9)	0.0659 (3)
H4	−0.1689	0.1019	−0.4757	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0326 (17)	0.059 (2)	0.0439 (19)	0.0020 (16)	0.0116 (15)	0.0034 (16)
C2	0.0425 (19)	0.056 (2)	0.0388 (18)	0.0019 (16)	0.0090 (15)	0.0121 (16)
C3	0.0371 (17)	0.0453 (18)	0.0431 (18)	−0.0015 (14)	0.0141 (15)	0.0084 (15)
C4	0.0344 (17)	0.0406 (17)	0.0392 (17)	0.0012 (13)	0.0147 (14)	0.0079 (14)
C5	0.0349 (17)	0.0433 (18)	0.049 (2)	−0.0014 (14)	0.0176 (15)	0.0065 (15)
C6	0.0309 (17)	0.049 (2)	0.056 (2)	−0.0069 (15)	0.0172 (16)	−0.0008 (17)
C7	0.048 (2)	0.049 (2)	0.046 (2)	−0.0007 (16)	0.0118 (17)	0.0204 (16)
C8	0.057 (2)	0.057 (2)	0.060 (2)	−0.0175 (18)	0.0081 (19)	0.0317 (19)
C9	0.074 (3)	0.090 (3)	0.066 (3)	−0.021 (2)	0.032 (2)	0.030 (2)
C10	0.053 (2)	0.065 (2)	0.074 (3)	−0.0110 (19)	0.037 (2)	0.012 (2)
C11	0.077 (3)	0.064 (3)	0.075 (3)	−0.013 (2)	0.045 (2)	−0.007 (2)
C12	0.059 (3)	0.073 (3)	0.092 (3)	0.017 (2)	0.037 (2)	0.024 (3)
C13	0.0336 (17)	0.0399 (17)	0.0416 (18)	−0.0004 (13)	0.0131 (14)	0.0070 (14)
C14	0.0403 (18)	0.0389 (18)	0.052 (2)	−0.0026 (14)	0.0164 (16)	0.0085 (15)
C15	0.0365 (18)	0.047 (2)	0.059 (2)	−0.0058 (15)	0.0186 (16)	0.0028 (17)
C16	0.0332 (17)	0.056 (2)	0.047 (2)	0.0004 (15)	0.0132 (15)	0.0055 (16)
C17	0.0379 (18)	0.058 (2)	0.0435 (19)	0.0015 (16)	0.0138 (15)	0.0138 (16)
C18	0.0342 (17)	0.0443 (18)	0.0424 (18)	0.0008 (14)	0.0150 (14)	0.0104 (14)
C19	0.0378 (18)	0.0455 (18)	0.0426 (19)	0.0020 (14)	0.0159 (15)	0.0148 (15)
C20	0.0462 (19)	0.0381 (17)	0.0417 (18)	−0.0084 (14)	0.0138 (15)	0.0113 (14)
C21	0.0410 (19)	0.053 (2)	0.054 (2)	−0.0061 (16)	0.0169 (16)	0.0169 (17)
C22	0.048 (2)	0.054 (2)	0.060 (2)	0.0040 (17)	0.0252 (18)	0.0183 (18)
C23	0.074 (3)	0.063 (3)	0.063 (3)	−0.011 (2)	0.028 (2)	0.005 (2)
C24	0.079 (3)	0.066 (3)	0.071 (3)	−0.008 (2)	0.038 (2)	0.022 (2)
Co1	0.0278 (2)	0.0329 (2)	0.0329 (2)	−0.00619 (16)	0.00689 (17)	0.01176 (17)
N1	0.0420 (16)	0.0451 (16)	0.0528 (17)	−0.0079 (13)	0.0119 (14)	0.0179 (13)
N2	0.0532 (18)	0.0510 (17)	0.0589 (19)	−0.0032 (14)	0.0285 (15)	0.0107 (15)
N3	0.0354 (14)	0.0402 (15)	0.0440 (16)	−0.0024 (12)	0.0149 (13)	0.0128 (12)
N4	0.0480 (17)	0.0489 (17)	0.0499 (17)	−0.0031 (13)	0.0230 (14)	0.0134 (13)
O1	0.0384 (13)	0.0505 (13)	0.0474 (13)	−0.0090 (10)	0.0072 (10)	0.0174 (11)
O2	0.0438 (13)	0.0453 (13)	0.0446 (13)	−0.0062 (10)	0.0060 (10)	0.0152 (10)
S1	0.0502 (5)	0.0510 (5)	0.0719 (7)	−0.0105 (4)	0.0145 (5)	0.0242 (5)
S2	0.0368 (5)	0.0930 (8)	0.0551 (6)	−0.0024 (5)	0.0001 (4)	0.0128 (5)
S3	0.0628 (6)	0.0505 (6)	0.0667 (6)	−0.0164 (5)	0.0108 (5)	0.0243 (5)
S4	0.0386 (5)	0.0860 (7)	0.0545 (6)	−0.0090 (5)	0.0002 (4)	0.0098 (5)

Geometric parameters (Å, º) top

C1—C2	1.368 (4)	C14—S3	1.733 (3)
C1—C6	1.397 (5)	C15—C16	1.389 (5)
C1—S2	1.743 (3)	C15—H15	0.9300
C2—C3	1.402 (4)	C16—C17	1.371 (4)
C2—H2	0.9300	C16—S4	1.742 (3)
C3—C4	1.420 (4)	C17—C18	1.398 (4)
C3—C7	1.440 (4)	C17—H17	0.9300
C4—O1	1.297 (4)	C18—C19	1.447 (4)
C4—C5	1.426 (4)	C19—N3	1.287 (4)
C5—C6	1.367 (4)	C19—H19	0.9300
C5—S1	1.740 (3)	C20—N3	1.486 (3)
C6—H6	0.9300	C20—C21	1.525 (4)
C7—N1	1.280 (4)	C20—H20A	0.9700
C7—H7	0.9300	C20—H20B	0.9700
C8—N1	1.467 (4)	C21—C22	1.519 (5)
C8—C9	1.533 (6)	C21—H21A	0.9700
C8—H8A	0.9700	C21—H21B	0.9700
C8—H8B	0.9700	C22—N4	1.460 (4)
C9—C10	1.533 (5)	C22—H22A	0.9700
C9—H9A	0.9700	C22—H22B	0.9700
C9—H9B	0.9700	C23—N4	1.462 (4)
C10—N2	1.479 (4)	C23—H23A	0.9600
C10—H10A	0.9700	C23—H23B	0.9600
C10—H10B	0.9700	C23—H23C	0.9600
C11—N2	1.465 (5)	C24—N4	1.448 (4)
C11—H11A	0.9600	C24—H24A	0.9600
C11—H11B	0.9600	C24—H24B	0.9600
C11—H11C	0.9600	C24—H24C	0.9600
C12—N2	1.475 (5)	Co1—O2	1.922 (2)
C12—H12A	0.9600	Co1—O1	1.925 (2)
C12—H12B	0.9600	Co1—N1	2.003 (3)
C12—H12C	0.9600	Co1—N3	2.011 (2)
C13—O2	1.290 (4)	S1—H1	1.2000
C13—C18	1.422 (4)	S2—H2A	1.2000
C13—C14	1.429 (4)	S3—H3	1.2000
C14—C15	1.367 (5)	S4—H4	1.2000

C2—C1—C6	120.4 (3)	C16—C17—C18	120.6 (3)
C2—C1—S2	120.4 (3)	C16—C17—H17	119.7
C6—C1—S2	119.2 (3)	C18—C17—H17	119.7
C1—C2—C3	120.4 (3)	C17—C18—C13	121.0 (3)
C1—C2—H2	119.8	C17—C18—C19	117.8 (3)
C3—C2—H2	119.8	C13—C18—C19	121.2 (3)
C2—C3—C4	121.4 (3)	N3—C19—C18	127.0 (3)
C2—C3—C7	117.2 (3)	N3—C19—H19	116.5
C4—C3—C7	121.3 (3)	C18—C19—H19	116.5
O1—C4—C3	124.6 (3)	N3—C20—C21	110.5 (2)
O1—C4—C5	120.2 (3)	N3—C20—H20A	109.6
C3—C4—C5	115.2 (3)	C21—C20—H20A	109.6
C6—C5—C4	123.3 (3)	N3—C20—H20B	109.6
C6—C5—S1	119.1 (2)	C21—C20—H20B	109.6
C4—C5—S1	117.7 (2)	H20A—C20—H20B	108.1
C5—C6—C1	119.4 (3)	C22—C21—C20	114.2 (3)
C5—C6—H6	120.3	C22—C21—H21A	108.7
C1—C6—H6	120.3	C20—C21—H21A	108.7
N1—C7—C3	126.6 (3)	C22—C21—H21B	108.7
N1—C7—H7	116.7	C20—C21—H21B	108.7
C3—C7—H7	116.7	H21A—C21—H21B	107.6
N1—C8—C9	110.0 (3)	N4—C22—C21	112.0 (3)
N1—C8—H8A	109.7	N4—C22—H22A	109.2
C9—C8—H8A	109.7	C21—C22—H22A	109.2
N1—C8—H8B	109.7	N4—C22—H22B	109.2
C9—C8—H8B	109.7	C21—C22—H22B	109.2
H8A—C8—H8B	108.2	H22A—C22—H22B	107.9
C10—C9—C8	117.0 (3)	N4—C23—H23A	109.5
C10—C9—H9A	108.0	N4—C23—H23B	109.5
C8—C9—H9A	108.0	H23A—C23—H23B	109.5
C10—C9—H9B	108.0	N4—C23—H23C	109.5
C8—C9—H9B	108.0	H23A—C23—H23C	109.5
H9A—C9—H9B	107.3	H23B—C23—H23C	109.5
N2—C10—C9	114.7 (3)	N4—C24—H24A	109.5
N2—C10—H10A	108.6	N4—C24—H24B	109.5
C9—C10—H10A	108.6	H24A—C24—H24B	109.5
N2—C10—H10B	108.6	N4—C24—H24C	109.5
C9—C10—H10B	108.6	H24A—C24—H24C	109.5
H10A—C10—H10B	107.6	H24B—C24—H24C	109.5
N2—C11—H11A	109.5	O2—Co1—O1	173.14 (10)
N2—C11—H11B	109.5	O2—Co1—N1	89.21 (10)
H11A—C11—H11B	109.5	O1—Co1—N1	90.08 (10)
N2—C11—H11C	109.5	O2—Co1—N3	90.29 (9)
H11A—C11—H11C	109.5	O1—Co1—N3	89.40 (9)
H11B—C11—H11C	109.5	N1—Co1—N3	171.48 (11)
N2—C12—H12A	109.5	C7—N1—C8	116.5 (3)
N2—C12—H12B	109.5	C7—N1—Co1	125.1 (2)
H12A—C12—H12B	109.5	C8—N1—Co1	118.3 (2)
N2—C12—H12C	109.5	C11—N2—C12	109.4 (3)
H12A—C12—H12C	109.5	C11—N2—C10	112.0 (3)
H12B—C12—H12C	109.5	C12—N2—C10	108.0 (3)
O2—C13—C18	124.4 (3)	C19—N3—C20	115.0 (3)
O2—C13—C14	120.1 (3)	C19—N3—Co1	124.1 (2)
C18—C13—C14	115.6 (3)	C20—N3—Co1	120.83 (19)
C15—C14—C13	122.9 (3)	C24—N4—C22	111.6 (3)
C15—C14—S3	119.1 (2)	C24—N4—C23	110.9 (3)
C13—C14—S3	118.0 (2)	C22—N4—C23	111.7 (3)
C14—C15—C16	119.5 (3)	C4—O1—Co1	128.2 (2)
C14—C15—H15	120.2	C13—O2—Co1	128.09 (19)
C16—C15—H15	120.2	C5—S1—H1	109.5
C17—C16—C15	120.5 (3)	C1—S2—H2A	109.5
C17—C16—S4	121.0 (3)	C14—S3—H3	109.5
C15—C16—S4	118.5 (3)	C16—S4—H4	109.5

Experimental details

Crystal data
Chemical formula	[Co(C₁₂H₁₇N₂OS₂)₂]
M_r	597.72
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.4100 (18), 12.5482 (18), 12.6032 (18)
α, β, γ (°)	103.272 (8), 110.910 (8), 90.612 (8)
V (Å³)	1346.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.40 × 0.30 × 0.30

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.696, 0.758
No. of measured, independent and observed [I > 2σ(I)] reflections	7433, 5221, 3718
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.129, 1.02
No. of reflections	5221
No. of parameters	324
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.58

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—O2	1.922 (2)	Co1—N1	2.003 (3)
Co1—O1	1.925 (2)	Co1—N3	2.011 (2)

Acknowledgements

The project was supported by the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, Educational Commission of Hubei Province (D20091703) and the Natural Science Foundation of Hubei Province (2008CDB038).

References

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