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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1113.
Published online 2009 August 22. doi:  10.1107/S1600536809032425
PMCID: PMC2970037

Bis(2-cyclo­hexyl­imino­methyl-4,6-disulfanylphenolato)nickel(II) acetonitrile solvate

Abstract

In the title compound, [Ni(C13H16NOS2)2]·CH3CN, the NiII atom is four-coordinated by two N,O-bidentate Schiff base ligands, resulting in a distorted tetra­hedral coordination for the metal ion.

Related literature

For background, 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-m1113-scheme1.jpg

Experimental

Crystal data

  • [Ni(C13H16NOS2)2]·C2H3N
  • M r = 632.54
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1113-efi1.jpg
  • a = 9.483 (2) Å
  • b = 15.879 (4) Å
  • c = 20.335 (4) Å
  • β = 94.10 (1)°
  • V = 3054.2 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.94 mm−1
  • T = 296 K
  • 0.35 × 0.27 × 0.22 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.735, T max = 0.820
  • 15868 measured reflections
  • 5366 independent reflections
  • 3750 reflections with I > 2σ(I)
  • R int = 0.027
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.166
  • S = 1.02
  • 5366 reflections
  • 348 parameters
  • H-atom parameters constrained
  • Δρmax = 0.47 e Å−3
  • Δρmin = −0.60 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 geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032425/hb5049sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032425/hb5049Isup2.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 NiII is four-coordinated in a distort tetrahedral configuration by two N atoms and two O atoms of the Schiff base ligands.

Experimental

A mixture of 2-hydroxy-3,5-dimercaptobenzaldehyde (372 mg, 2 mmol), cyclohexanamine (198 mg, 2 mmol) and NiCl2.6H2O (1 mmol, 236 mg) in acetonitrile (10 ml) was stirred for 1 h. After keeping the filtrate in air for 9 d, green blocks of (I) were formed.

Refinement

The H atoms were positioned geometrically (C—H = 0.93–0.97Å, 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 (I) showing 30% probability displacement ellipsoids.

Crystal data

[Ni(C13H16NOS2)2]·C2H3NF(000) = 1328
Mr = 632.54Dx = 1.376 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 9.483 (2) Åθ = 9–12°
b = 15.879 (4) ŵ = 0.94 mm1
c = 20.335 (4) ÅT = 296 K
β = 94.10 (1)°Block, green
V = 3054.2 (12) Å30.35 × 0.27 × 0.22 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer5366 independent reflections
Radiation source: fine-focus sealed tube3750 reflections with I > 2σ(I)
graphiteRint = 0.027
ω/2θ scansθmax = 25.0°, θmin = 1.6°
Absorption correction: ψ scan (North et al., 1968)h = −11→11
Tmin = 0.735, Tmax = 0.820k = −13→18
15868 measured reflectionsl = −24→22

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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.099P)2 + 1.0949P] where P = (Fo2 + 2Fc2)/3
5366 reflections(Δ/σ)max = 0.001
348 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = −0.60 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
Ni10.71327 (5)0.75018 (3)0.18476 (2)0.05582 (19)
S20.26353 (13)0.63623 (8)0.12076 (7)0.0863 (4)
H20.33440.62060.17050.129*
S31.23712 (14)0.60737 (8)0.43291 (7)0.0908 (4)
H31.32750.58510.39840.136*
S40.79783 (18)0.81852 (8)0.40833 (6)0.0977 (5)
H40.67620.79700.40380.147*
S10.13179 (17)0.90908 (12)−0.02558 (9)0.1251 (6)
H10.16600.9015−0.08100.188*
O10.5238 (3)0.72316 (17)0.15565 (13)0.0613 (6)
N10.8485 (3)0.65868 (19)0.16717 (14)0.0536 (7)
N20.7138 (3)0.86444 (18)0.14541 (15)0.0557 (7)
O20.7561 (3)0.75360 (16)0.27700 (13)0.0637 (7)
C60.4421 (4)0.7675 (2)0.11519 (18)0.0536 (9)
C70.8643 (4)0.7192 (2)0.30842 (18)0.0545 (9)
C80.6061 (4)0.8918 (2)0.10958 (19)0.0629 (10)
H80.61320.94630.09350.076*
C90.9529 (4)0.6585 (2)0.28132 (17)0.0525 (8)
C100.4764 (4)0.8483 (2)0.09145 (18)0.0563 (9)
C110.9349 (4)0.6301 (2)0.21331 (18)0.0533 (8)
H110.99280.58600.20190.064*
C121.0666 (4)0.6232 (2)0.32019 (19)0.0605 (9)
H121.12330.58270.30220.073*
C130.8493 (4)0.6203 (2)0.10085 (18)0.0606 (9)
H130.94170.59410.09630.073*
C140.3781 (4)0.8914 (3)0.0477 (2)0.0724 (11)
H140.40040.94440.03200.087*
C150.2163 (4)0.7773 (3)0.0500 (2)0.0734 (12)
H150.12990.75340.03590.088*
C160.2523 (5)0.8559 (3)0.0285 (2)0.0796 (13)
C170.8334 (4)0.9231 (3)0.1596 (2)0.0653 (10)
H170.83400.96420.12370.078*
C180.3084 (4)0.7349 (3)0.0923 (2)0.0626 (10)
C191.0113 (5)0.7079 (3)0.4122 (2)0.0705 (11)
H191.03050.72470.45580.085*
C201.0944 (4)0.6480 (2)0.3841 (2)0.0651 (10)
C210.8255 (5)0.6871 (3)0.04867 (19)0.0704 (11)
H21A0.89940.72920.05440.084*
H21B0.73570.71470.05380.084*
C220.9003 (5)0.7419 (2)0.3745 (2)0.0652 (11)
C230.7365 (6)0.5537 (3)0.0916 (2)0.0792 (13)
H23A0.64510.57840.09830.095*
H23B0.75440.50960.12410.095*
C240.7174 (7)0.5820 (3)−0.0312 (2)0.0996 (17)
H24A0.72720.5560−0.07380.119*
H24B0.62360.6063−0.03160.119*
C250.8253 (6)0.6502 (3)−0.0205 (2)0.0934 (16)
H25A0.80560.6945−0.05260.112*
H25B0.91820.6276−0.02720.112*
C270.8141 (5)0.9695 (3)0.2230 (3)0.0917 (16)
H27A0.80950.92940.25880.110*
H27B0.72581.00050.21910.110*
C280.9709 (4)0.8773 (3)0.1640 (3)0.0867 (15)
H28A0.98350.84940.12240.104*
H28B0.96990.83440.19800.104*
C260.7338 (7)0.5155 (3)0.0220 (2)0.1025 (17)
H26A0.82090.48470.01750.123*
H26B0.65600.47590.01630.123*
C291.0753 (5)0.9852 (4)0.2428 (3)0.1024 (17)
H29A1.07890.94630.27960.123*
H29B1.15161.02540.25050.123*
C300.9370 (6)1.0306 (4)0.2386 (3)0.118 (2)
H30A0.93701.07320.20440.141*
H30B0.92461.05870.28010.141*
C311.0947 (5)0.9375 (4)0.1802 (3)0.113 (2)
H31A1.18210.90570.18490.135*
H31B1.10150.97700.14410.135*
C320.4297 (7)0.8572 (5)0.2992 (4)0.118 (2)
C330.4114 (8)0.7686 (4)0.3059 (4)0.136 (3)
H33A0.41860.75380.35180.204*
H33B0.48320.73960.28380.204*
H33C0.31990.75270.28660.204*
N30.4466 (8)0.9245 (5)0.2955 (5)0.202 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0539 (3)0.0583 (3)0.0548 (3)0.0049 (2)0.0010 (2)0.0045 (2)
S20.0703 (7)0.0812 (8)0.1054 (10)−0.0226 (6)−0.0069 (6)0.0092 (7)
S30.0947 (9)0.0854 (8)0.0856 (8)0.0120 (7)−0.0396 (7)0.0045 (6)
S40.1485 (13)0.0862 (8)0.0582 (7)0.0428 (8)0.0060 (7)−0.0134 (6)
S10.0975 (10)0.1409 (14)0.1285 (13)0.0185 (9)−0.0514 (9)0.0419 (11)
O10.0512 (14)0.0626 (15)0.0692 (17)0.0009 (12)−0.0019 (12)0.0147 (13)
N10.0524 (17)0.0566 (17)0.0514 (17)0.0010 (13)0.0013 (14)−0.0010 (13)
N20.0549 (18)0.0538 (17)0.0583 (18)−0.0018 (14)0.0027 (14)0.0042 (14)
O20.0707 (17)0.0704 (17)0.0496 (15)0.0234 (13)0.0009 (13)0.0020 (11)
C60.0460 (19)0.064 (2)0.051 (2)0.0031 (16)0.0047 (16)0.0011 (16)
C70.065 (2)0.0505 (19)0.048 (2)−0.0004 (18)0.0033 (17)0.0033 (16)
C80.071 (3)0.056 (2)0.061 (2)0.0054 (19)0.0038 (19)0.0138 (18)
C90.057 (2)0.0480 (19)0.052 (2)−0.0005 (16)0.0026 (16)0.0027 (15)
C100.053 (2)0.059 (2)0.057 (2)0.0036 (17)−0.0011 (16)0.0051 (17)
C110.050 (2)0.051 (2)0.058 (2)0.0045 (16)0.0020 (16)−0.0027 (16)
C120.059 (2)0.057 (2)0.063 (2)0.0004 (18)−0.0066 (18)0.0019 (18)
C130.066 (2)0.063 (2)0.052 (2)0.0069 (19)0.0013 (17)−0.0074 (17)
C140.069 (3)0.075 (3)0.071 (3)0.009 (2)−0.009 (2)0.016 (2)
C150.050 (2)0.100 (3)0.069 (3)0.005 (2)−0.0070 (19)−0.001 (2)
C160.069 (3)0.094 (3)0.073 (3)0.022 (2)−0.014 (2)0.009 (2)
C170.065 (2)0.061 (2)0.070 (3)−0.0159 (19)0.0038 (19)0.0089 (19)
C180.054 (2)0.074 (3)0.059 (2)0.0018 (18)0.0033 (18)−0.0036 (18)
C190.098 (3)0.057 (2)0.053 (2)−0.004 (2)−0.015 (2)0.0020 (19)
C200.069 (2)0.057 (2)0.067 (3)−0.0027 (19)−0.0175 (19)0.0079 (19)
C210.088 (3)0.067 (3)0.057 (2)−0.013 (2)0.011 (2)−0.0008 (19)
C220.092 (3)0.053 (2)0.050 (2)0.006 (2)0.002 (2)−0.0014 (16)
C230.116 (4)0.060 (2)0.059 (2)−0.018 (2)−0.005 (2)0.0038 (19)
C240.155 (5)0.075 (3)0.064 (3)−0.009 (3)−0.027 (3)−0.005 (2)
C250.142 (5)0.083 (3)0.057 (3)−0.002 (3)0.019 (3)0.004 (2)
C270.068 (3)0.077 (3)0.131 (4)−0.008 (2)0.017 (3)−0.041 (3)
C280.060 (3)0.097 (3)0.105 (4)−0.015 (2)0.021 (2)−0.041 (3)
C260.168 (5)0.062 (3)0.074 (3)−0.014 (3)−0.015 (3)−0.010 (2)
C290.078 (3)0.119 (4)0.110 (4)−0.035 (3)0.008 (3)−0.037 (3)
C300.101 (4)0.096 (4)0.158 (6)−0.029 (3)0.028 (4)−0.062 (4)
C310.065 (3)0.130 (5)0.148 (5)−0.036 (3)0.031 (3)−0.061 (4)
C320.093 (4)0.105 (5)0.159 (6)−0.015 (4)0.020 (4)0.009 (4)
C330.178 (7)0.111 (5)0.130 (6)−0.026 (4)0.081 (5)−0.016 (4)
N30.146 (6)0.105 (5)0.350 (13)−0.024 (4)−0.011 (6)0.050 (6)

Geometric parameters (Å, °)

Ni1—O21.891 (3)C17—C271.507 (6)
Ni1—O11.900 (3)C17—H170.9800
Ni1—N21.983 (3)C19—C221.368 (6)
Ni1—N11.987 (3)C19—C201.386 (6)
S2—C181.734 (4)C19—H190.9300
S2—H21.2000C21—C251.523 (6)
S3—C201.744 (4)C21—H21A0.9700
S3—H31.2000C21—H21B0.9700
S4—C221.731 (4)C23—C261.537 (6)
S4—H41.2000C23—H23A0.9700
S1—C161.746 (4)C23—H23B0.9700
S1—H11.2000C24—C251.495 (7)
O1—C61.297 (4)C24—C261.513 (7)
N1—C111.283 (4)C24—H24A0.9700
N1—C131.481 (5)C24—H24B0.9700
N2—C81.287 (5)C25—H25A0.9700
N2—C171.480 (5)C25—H25B0.9700
O2—C71.291 (4)C27—C301.532 (6)
C6—C101.417 (5)C27—H27A0.9700
C6—C181.417 (5)C27—H27B0.9700
C7—C221.409 (5)C28—C311.531 (6)
C7—C91.415 (5)C28—H28A0.9700
C8—C101.436 (5)C28—H28B0.9700
C8—H80.9300C26—H26A0.9700
C9—C121.407 (5)C26—H26B0.9700
C9—C111.453 (5)C29—C301.493 (8)
C10—C141.418 (5)C29—C311.504 (7)
C11—H110.9300C29—H29A0.9700
C12—C201.365 (5)C29—H29B0.9700
C12—H120.9300C30—H30A0.9700
C13—C231.505 (6)C30—H30B0.9700
C13—C211.506 (6)C31—H31A0.9700
C13—H130.9800C31—H31B0.9700
C14—C161.351 (6)C32—N31.085 (8)
C14—H140.9300C32—C331.424 (9)
C15—C181.358 (6)C33—H33A0.9600
C15—C161.374 (7)C33—H33B0.9600
C15—H150.9300C33—H33C0.9600
C17—C281.490 (6)
O2—Ni1—O1116.53 (12)C13—C21—H21A109.3
O2—Ni1—N2111.55 (12)C25—C21—H21A109.3
O1—Ni1—N296.35 (12)C13—C21—H21B109.3
O2—Ni1—N195.97 (11)C25—C21—H21B109.3
O1—Ni1—N1112.76 (12)H21A—C21—H21B107.9
N2—Ni1—N1125.16 (12)C19—C22—C7124.0 (4)
C18—S2—H2109.5C19—C22—S4119.0 (3)
C20—S3—H3109.5C7—C22—S4117.0 (3)
C22—S4—H4109.5C13—C23—C26110.9 (4)
C16—S1—H1109.5C13—C23—H23A109.4
C6—O1—Ni1125.7 (2)C26—C23—H23A109.4
C11—N1—C13118.4 (3)C13—C23—H23B109.4
C11—N1—Ni1120.9 (2)C26—C23—H23B109.4
C13—N1—Ni1120.7 (2)H23A—C23—H23B108.0
C8—N2—C17117.7 (3)C25—C24—C26111.5 (4)
C8—N2—Ni1120.8 (3)C25—C24—H24A109.3
C17—N2—Ni1121.4 (2)C26—C24—H24A109.3
C7—O2—Ni1125.8 (2)C25—C24—H24B109.3
O1—C6—C10124.5 (3)C26—C24—H24B109.3
O1—C6—C18119.4 (3)H24A—C24—H24B108.0
C10—C6—C18116.1 (3)C24—C25—C21111.6 (4)
O2—C7—C22119.6 (3)C24—C25—H25A109.3
O2—C7—C9124.7 (3)C21—C25—H25A109.3
C22—C7—C9115.8 (3)C24—C25—H25B109.3
N2—C8—C10127.9 (3)C21—C25—H25B109.3
N2—C8—H8116.1H25A—C25—H25B108.0
C10—C8—H8116.1C17—C27—C30110.4 (4)
C12—C9—C7120.3 (3)C17—C27—H27A109.6
C12—C9—C11116.4 (3)C30—C27—H27A109.6
C7—C9—C11123.3 (3)C17—C27—H27B109.6
C6—C10—C14119.6 (3)C30—C27—H27B109.6
C6—C10—C8124.2 (3)H27A—C27—H27B108.1
C14—C10—C8116.2 (4)C17—C28—C31111.2 (4)
N1—C11—C9127.7 (3)C17—C28—H28A109.4
N1—C11—H11116.1C31—C28—H28A109.4
C9—C11—H11116.1C17—C28—H28B109.4
C20—C12—C9120.6 (4)C31—C28—H28B109.4
C20—C12—H12119.7H28A—C28—H28B108.0
C9—C12—H12119.7C24—C26—C23112.1 (4)
N1—C13—C23110.7 (3)C24—C26—H26A109.2
N1—C13—C21109.9 (3)C23—C26—H26A109.2
C23—C13—C21109.7 (3)C24—C26—H26B109.2
N1—C13—H13108.8C23—C26—H26B109.2
C23—C13—H13108.8H26A—C26—H26B107.9
C21—C13—H13108.8C30—C29—C31110.8 (5)
C16—C14—C10120.5 (4)C30—C29—H29A109.5
C16—C14—H14119.8C31—C29—H29A109.5
C10—C14—H14119.8C30—C29—H29B109.5
C18—C15—C16119.2 (4)C31—C29—H29B109.5
C18—C15—H15120.4H29A—C29—H29B108.1
C16—C15—H15120.4C29—C30—C27111.0 (4)
C14—C16—C15121.4 (4)C29—C30—H30A109.4
C14—C16—S1120.3 (4)C27—C30—H30A109.4
C15—C16—S1118.3 (4)C29—C30—H30B109.4
N2—C17—C28111.1 (3)C27—C30—H30B109.4
N2—C17—C27109.7 (3)H30A—C30—H30B108.0
C28—C17—C27110.3 (4)C29—C31—C28111.0 (4)
N2—C17—H17108.6C29—C31—H31A109.4
C28—C17—H17108.6C28—C31—H31A109.4
C27—C17—H17108.6C29—C31—H31B109.4
C15—C18—C6123.2 (4)C28—C31—H31B109.4
C15—C18—S2119.8 (3)H31A—C31—H31B108.0
C6—C18—S2117.1 (3)N3—C32—C33178.0 (10)
C22—C19—C20118.4 (4)C32—C33—H33A109.5
C22—C19—H19120.8C32—C33—H33B109.5
C20—C19—H19120.8H33A—C33—H33B109.5
C12—C20—C19120.9 (4)C32—C33—H33C109.5
C12—C20—S3121.7 (3)H33A—C33—H33C109.5
C19—C20—S3117.4 (3)H33B—C33—H33C109.5
C13—C21—C25111.7 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5049).

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