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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1073.
Published online 2009 August 15. doi:  10.1107/S1600536809031389
PMCID: PMC2970151

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

Abstract

In the title mononuclear complex, [Co(C12H17N2OS2)2], the CoII 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 [triangle]); Xu et al. (2009 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-m1073-scheme1.jpg

Experimental

Crystal data

  • [Co(C12H17N2OS2)2]
  • M r = 597.72
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1073-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.129
  • S = 1.02
  • 5221 reflections
  • 324 parameters
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.58 e Å−3

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

Table 1
Selected bond lengths (Å)

Supplementary Material

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

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

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

Acknowledgments

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).

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All H atoms were positioned geometrically (C—H = 0.93–0.96Å, S—H = 1.20Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).

Figures

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

Crystal data

[Co(C12H17N2OS2)2]Z = 2
Mr = 597.72F(000) = 626
Triclinic, P1Dx = 1.475 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4100 (18) ÅCell parameters from 25 reflections
b = 12.5482 (18) Åθ = 9–12°
c = 12.6032 (18) ŵ = 0.98 mm1
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

Enraf–Nonius CAD-4 diffractometer5221 independent reflections
Radiation source: fine-focus sealed tube3718 reflections with I > 2σ(I)
graphiteRint = 0.022
ω/2θ scansθmax = 26.0°, θmin = 1.7°
Absorption correction: ψ scan (North et al., 1968)h = −11→9
Tmin = 0.696, Tmax = 0.758k = −15→15
7433 measured reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0746P)2 + 0.0983P] where P = (Fo2 + 2Fc2)/3
5221 reflections(Δ/σ)max = 0.044
324 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = −0.58 e Å3

Special details

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)

xyzUiso*/Ueq
C11.0983 (4)0.3759 (3)0.4418 (3)0.0477 (8)
C20.9888 (4)0.2914 (3)0.4161 (3)0.0476 (8)
H21.00800.23950.46040.057*
C30.8478 (4)0.2825 (3)0.3235 (3)0.0425 (7)
C40.8150 (3)0.3595 (2)0.2533 (3)0.0381 (7)
C50.9338 (3)0.4458 (3)0.2854 (3)0.0425 (7)
C61.0703 (4)0.4550 (3)0.3766 (3)0.0476 (8)
H61.14390.51330.39520.057*
C70.7338 (4)0.1967 (3)0.3078 (3)0.0481 (8)
H70.75790.15590.36370.058*
C80.4970 (4)0.0922 (3)0.2368 (3)0.0589 (10)
H8A0.55370.05140.29230.071*
H8B0.44440.04020.16170.071*
C90.3798 (5)0.1534 (4)0.2797 (4)0.0736 (12)
H9A0.32090.10080.29750.088*
H9B0.43530.20750.35260.088*
C100.2674 (4)0.2124 (3)0.1965 (4)0.0615 (10)
H10A0.21080.15880.12350.074*
H10B0.19450.24180.23100.074*
C110.4185 (5)0.3916 (3)0.2747 (4)0.0718 (12)
H11A0.44590.45450.25220.108*
H11B0.50920.36680.32340.108*
H11C0.35230.41140.31750.108*
C120.2176 (4)0.3474 (3)0.0846 (4)0.0714 (12)
H12A0.14710.37820.11970.107*
H12B0.16420.28920.01630.107*
H12C0.26230.40360.06240.107*
C130.2718 (3)0.0922 (2)−0.0969 (3)0.0392 (7)
C140.1551 (4)0.0039 (3)−0.1298 (3)0.0444 (8)
C150.0298 (4)−0.0161 (3)−0.2317 (3)0.0491 (8)
H15−0.0441−0.0741−0.24960.059*
C160.0137 (4)0.0506 (3)−0.3085 (3)0.0473 (8)
C170.1211 (4)0.1372 (3)−0.2818 (3)0.0468 (8)
H170.10890.1814−0.33380.056*
C180.2487 (3)0.1596 (3)−0.1770 (3)0.0402 (7)
C190.3602 (4)0.2499 (3)−0.1558 (3)0.0410 (7)
H190.34460.2842−0.21650.049*
C200.5820 (4)0.3734 (2)−0.0702 (3)0.0426 (8)
H20A0.61340.43270.00070.051*
H20B0.52780.4038−0.13600.051*
C210.7228 (4)0.3244 (3)−0.0862 (3)0.0492 (8)
H21A0.78570.3812−0.09480.059*
H21B0.78220.3021−0.01580.059*
C220.6870 (4)0.2261 (3)−0.1911 (3)0.0518 (9)
H22A0.78190.2021−0.19750.062*
H22B0.63420.1659−0.17880.062*
C230.5051 (5)0.1534 (3)−0.3889 (4)0.0679 (11)
H23A0.44580.1732−0.45980.102*
H23B0.43810.1203−0.36050.102*
H23C0.57440.1020−0.40440.102*
C240.6821 (5)0.3107 (3)−0.3452 (4)0.0685 (11)
H24A0.75780.2658−0.36090.103*
H24B0.73180.3779−0.28800.103*
H24C0.61640.3272−0.41630.103*
Co10.52925 (4)0.23544 (3)0.08521 (3)0.03191 (14)
N10.6028 (3)0.1710 (2)0.2245 (2)0.0474 (7)
N20.3391 (3)0.3031 (2)0.1696 (3)0.0528 (7)
N30.4787 (3)0.2878 (2)−0.0621 (2)0.0394 (6)
N40.5922 (3)0.2520 (2)−0.3004 (2)0.0474 (7)
O10.6877 (2)0.35591 (18)0.16610 (19)0.0471 (5)
O20.3892 (2)0.10552 (17)−0.00081 (19)0.0468 (5)
S10.90029 (11)0.54412 (8)0.20420 (9)0.0586 (3)
H10.86630.49940.10230.088*
S21.27446 (11)0.38591 (10)0.55553 (9)0.0675 (3)
H2A1.29500.29820.57810.101*
S30.17582 (12)−0.08143 (8)−0.03595 (9)0.0622 (3)
H30.2279−0.02760.06380.093*
S4−0.14439 (11)0.02070 (9)−0.43967 (9)0.0659 (3)
H4−0.16890.1019−0.47570.099*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0326 (17)0.059 (2)0.0439 (19)0.0020 (16)0.0116 (15)0.0034 (16)
C20.0425 (19)0.056 (2)0.0388 (18)0.0019 (16)0.0090 (15)0.0121 (16)
C30.0371 (17)0.0453 (18)0.0431 (18)−0.0015 (14)0.0141 (15)0.0084 (15)
C40.0344 (17)0.0406 (17)0.0392 (17)0.0012 (13)0.0147 (14)0.0079 (14)
C50.0349 (17)0.0433 (18)0.049 (2)−0.0014 (14)0.0176 (15)0.0065 (15)
C60.0309 (17)0.049 (2)0.056 (2)−0.0069 (15)0.0172 (16)−0.0008 (17)
C70.048 (2)0.049 (2)0.046 (2)−0.0007 (16)0.0118 (17)0.0204 (16)
C80.057 (2)0.057 (2)0.060 (2)−0.0175 (18)0.0081 (19)0.0317 (19)
C90.074 (3)0.090 (3)0.066 (3)−0.021 (2)0.032 (2)0.030 (2)
C100.053 (2)0.065 (2)0.074 (3)−0.0110 (19)0.037 (2)0.012 (2)
C110.077 (3)0.064 (3)0.075 (3)−0.013 (2)0.045 (2)−0.007 (2)
C120.059 (3)0.073 (3)0.092 (3)0.017 (2)0.037 (2)0.024 (3)
C130.0336 (17)0.0399 (17)0.0416 (18)−0.0004 (13)0.0131 (14)0.0070 (14)
C140.0403 (18)0.0389 (18)0.052 (2)−0.0026 (14)0.0164 (16)0.0085 (15)
C150.0365 (18)0.047 (2)0.059 (2)−0.0058 (15)0.0186 (16)0.0028 (17)
C160.0332 (17)0.056 (2)0.047 (2)0.0004 (15)0.0132 (15)0.0055 (16)
C170.0379 (18)0.058 (2)0.0435 (19)0.0015 (16)0.0138 (15)0.0138 (16)
C180.0342 (17)0.0443 (18)0.0424 (18)0.0008 (14)0.0150 (14)0.0104 (14)
C190.0378 (18)0.0455 (18)0.0426 (19)0.0020 (14)0.0159 (15)0.0148 (15)
C200.0462 (19)0.0381 (17)0.0417 (18)−0.0084 (14)0.0138 (15)0.0113 (14)
C210.0410 (19)0.053 (2)0.054 (2)−0.0061 (16)0.0169 (16)0.0169 (17)
C220.048 (2)0.054 (2)0.060 (2)0.0040 (17)0.0252 (18)0.0183 (18)
C230.074 (3)0.063 (3)0.063 (3)−0.011 (2)0.028 (2)0.005 (2)
C240.079 (3)0.066 (3)0.071 (3)−0.008 (2)0.038 (2)0.022 (2)
Co10.0278 (2)0.0329 (2)0.0329 (2)−0.00619 (16)0.00689 (17)0.01176 (17)
N10.0420 (16)0.0451 (16)0.0528 (17)−0.0079 (13)0.0119 (14)0.0179 (13)
N20.0532 (18)0.0510 (17)0.0589 (19)−0.0032 (14)0.0285 (15)0.0107 (15)
N30.0354 (14)0.0402 (15)0.0440 (16)−0.0024 (12)0.0149 (13)0.0128 (12)
N40.0480 (17)0.0489 (17)0.0499 (17)−0.0031 (13)0.0230 (14)0.0134 (13)
O10.0384 (13)0.0505 (13)0.0474 (13)−0.0090 (10)0.0072 (10)0.0174 (11)
O20.0438 (13)0.0453 (13)0.0446 (13)−0.0062 (10)0.0060 (10)0.0152 (10)
S10.0502 (5)0.0510 (5)0.0719 (7)−0.0105 (4)0.0145 (5)0.0242 (5)
S20.0368 (5)0.0930 (8)0.0551 (6)−0.0024 (5)0.0001 (4)0.0128 (5)
S30.0628 (6)0.0505 (6)0.0667 (6)−0.0164 (5)0.0108 (5)0.0243 (5)
S40.0386 (5)0.0860 (7)0.0545 (6)−0.0090 (5)0.0002 (4)0.0098 (5)

Geometric parameters (Å, °)

C1—C21.368 (4)C14—S31.733 (3)
C1—C61.397 (5)C15—C161.389 (5)
C1—S21.743 (3)C15—H150.9300
C2—C31.402 (4)C16—C171.371 (4)
C2—H20.9300C16—S41.742 (3)
C3—C41.420 (4)C17—C181.398 (4)
C3—C71.440 (4)C17—H170.9300
C4—O11.297 (4)C18—C191.447 (4)
C4—C51.426 (4)C19—N31.287 (4)
C5—C61.367 (4)C19—H190.9300
C5—S11.740 (3)C20—N31.486 (3)
C6—H60.9300C20—C211.525 (4)
C7—N11.280 (4)C20—H20A0.9700
C7—H70.9300C20—H20B0.9700
C8—N11.467 (4)C21—C221.519 (5)
C8—C91.533 (6)C21—H21A0.9700
C8—H8A0.9700C21—H21B0.9700
C8—H8B0.9700C22—N41.460 (4)
C9—C101.533 (5)C22—H22A0.9700
C9—H9A0.9700C22—H22B0.9700
C9—H9B0.9700C23—N41.462 (4)
C10—N21.479 (4)C23—H23A0.9600
C10—H10A0.9700C23—H23B0.9600
C10—H10B0.9700C23—H23C0.9600
C11—N21.465 (5)C24—N41.448 (4)
C11—H11A0.9600C24—H24A0.9600
C11—H11B0.9600C24—H24B0.9600
C11—H11C0.9600C24—H24C0.9600
C12—N21.475 (5)Co1—O21.922 (2)
C12—H12A0.9600Co1—O11.925 (2)
C12—H12B0.9600Co1—N12.003 (3)
C12—H12C0.9600Co1—N32.011 (2)
C13—O21.290 (4)S1—H11.2000
C13—C181.422 (4)S2—H2A1.2000
C13—C141.429 (4)S3—H31.2000
C14—C151.367 (5)S4—H41.2000
C2—C1—C6120.4 (3)C16—C17—C18120.6 (3)
C2—C1—S2120.4 (3)C16—C17—H17119.7
C6—C1—S2119.2 (3)C18—C17—H17119.7
C1—C2—C3120.4 (3)C17—C18—C13121.0 (3)
C1—C2—H2119.8C17—C18—C19117.8 (3)
C3—C2—H2119.8C13—C18—C19121.2 (3)
C2—C3—C4121.4 (3)N3—C19—C18127.0 (3)
C2—C3—C7117.2 (3)N3—C19—H19116.5
C4—C3—C7121.3 (3)C18—C19—H19116.5
O1—C4—C3124.6 (3)N3—C20—C21110.5 (2)
O1—C4—C5120.2 (3)N3—C20—H20A109.6
C3—C4—C5115.2 (3)C21—C20—H20A109.6
C6—C5—C4123.3 (3)N3—C20—H20B109.6
C6—C5—S1119.1 (2)C21—C20—H20B109.6
C4—C5—S1117.7 (2)H20A—C20—H20B108.1
C5—C6—C1119.4 (3)C22—C21—C20114.2 (3)
C5—C6—H6120.3C22—C21—H21A108.7
C1—C6—H6120.3C20—C21—H21A108.7
N1—C7—C3126.6 (3)C22—C21—H21B108.7
N1—C7—H7116.7C20—C21—H21B108.7
C3—C7—H7116.7H21A—C21—H21B107.6
N1—C8—C9110.0 (3)N4—C22—C21112.0 (3)
N1—C8—H8A109.7N4—C22—H22A109.2
C9—C8—H8A109.7C21—C22—H22A109.2
N1—C8—H8B109.7N4—C22—H22B109.2
C9—C8—H8B109.7C21—C22—H22B109.2
H8A—C8—H8B108.2H22A—C22—H22B107.9
C10—C9—C8117.0 (3)N4—C23—H23A109.5
C10—C9—H9A108.0N4—C23—H23B109.5
C8—C9—H9A108.0H23A—C23—H23B109.5
C10—C9—H9B108.0N4—C23—H23C109.5
C8—C9—H9B108.0H23A—C23—H23C109.5
H9A—C9—H9B107.3H23B—C23—H23C109.5
N2—C10—C9114.7 (3)N4—C24—H24A109.5
N2—C10—H10A108.6N4—C24—H24B109.5
C9—C10—H10A108.6H24A—C24—H24B109.5
N2—C10—H10B108.6N4—C24—H24C109.5
C9—C10—H10B108.6H24A—C24—H24C109.5
H10A—C10—H10B107.6H24B—C24—H24C109.5
N2—C11—H11A109.5O2—Co1—O1173.14 (10)
N2—C11—H11B109.5O2—Co1—N189.21 (10)
H11A—C11—H11B109.5O1—Co1—N190.08 (10)
N2—C11—H11C109.5O2—Co1—N390.29 (9)
H11A—C11—H11C109.5O1—Co1—N389.40 (9)
H11B—C11—H11C109.5N1—Co1—N3171.48 (11)
N2—C12—H12A109.5C7—N1—C8116.5 (3)
N2—C12—H12B109.5C7—N1—Co1125.1 (2)
H12A—C12—H12B109.5C8—N1—Co1118.3 (2)
N2—C12—H12C109.5C11—N2—C12109.4 (3)
H12A—C12—H12C109.5C11—N2—C10112.0 (3)
H12B—C12—H12C109.5C12—N2—C10108.0 (3)
O2—C13—C18124.4 (3)C19—N3—C20115.0 (3)
O2—C13—C14120.1 (3)C19—N3—Co1124.1 (2)
C18—C13—C14115.6 (3)C20—N3—Co1120.83 (19)
C15—C14—C13122.9 (3)C24—N4—C22111.6 (3)
C15—C14—S3119.1 (2)C24—N4—C23110.9 (3)
C13—C14—S3118.0 (2)C22—N4—C23111.7 (3)
C14—C15—C16119.5 (3)C4—O1—Co1128.2 (2)
C14—C15—H15120.2C13—O2—Co1128.09 (19)
C16—C15—H15120.2C5—S1—H1109.5
C17—C16—C15120.5 (3)C1—S2—H2A109.5
C17—C16—S4121.0 (3)C14—S3—H3109.5
C15—C16—S4118.5 (3)C16—S4—H4109.5

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5029).

References

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