Literature DB >> 24109261

Bis(1-ethyl-4,4'-bipyridin-1-ium) bis-(1,2-di-cyano-ethene-1,2-di-thiol-ato-κ(2) S,S')nickelate(II).

Yao Chen1, Wei-Hua Ning, Jian-Lan Liu.   

Abstract

In the anion of the title compound, (C12H13N2)[Ni(C4N2S2)2], the Ni(II) atom is coordinated by four S atoms from two 1,2-di-cyano-ethene-1,2-di-thiol-ate (mnt) ligands in a suqare-planar geometry. Weak C-H⋯N and C-H⋯S hydrogen bonds between the 1-ethyl-4,4'-bipyridin-1-ium cations and mnt anions and weak π-π inter-actions between the pyridine rings of the cations [centroid-centroid distances = 3.808 (3) and 3.972 (3) Å] lead to a two-dimensional network parallel to (010).

Entities:  

Year:  2013        PMID: 24109261      PMCID: PMC3793674          DOI: 10.1107/S1600536813015493

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For general background to bis­(1,2-di­thiol­ene) complexes acting as magnetic materials or showing non-linear optical properties, see: Duan et al. (2010 ▶); Kato (2004 ▶). For the synthesis of the compound, see: Pei et al. (2010 ▶). For related structures, see: Duan et al. (2011 ▶); Liu et al. (2011 ▶).

Experimental

Crystal data

(C12H13N2)[Ni(C4N2S2)2] M = 709.58 Triclinic, a = 7.4505 (13) Å b = 12.793 (2) Å c = 17.745 (3) Å α = 78.664 (2)° β = 86.558 (2)° γ = 80.344 (2)° V = 1634.2 (5) Å3 Z = 2 Mo Kα radiation μ = 0.89 mm−1 T = 296 K 0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.808, T max = 0.876 14954 measured reflections 7631 independent reflections 3616 reflections with I > 2σ(I) R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.128 S = 0.97 7631 reflections 408 parameters H-atom parameters constrained Δρmax = 0.49 e Å−3 Δρmin = −0.37 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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. Crystal structure: contains datablock(s) D, I. DOI: 10.1107/S1600536813015493/hy2630sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015493/hy2630Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
(C12H13N2)[Ni(C4N2S2)2]Z = 2
Mr = 709.58F(000) = 732.0
Triclinic, P1Dx = 1.442 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4505 (13) ÅCell parameters from 1518 reflections
b = 12.793 (2) Åθ = 2.3–19.7°
c = 17.745 (3) ŵ = 0.89 mm1
α = 78.664 (2)°T = 296 K
β = 86.558 (2)°Block, red
γ = 80.344 (2)°0.25 × 0.20 × 0.15 mm
V = 1634.2 (5) Å3
Bruker APEX CCD diffractometer7631 independent reflections
Radiation source: fine-focus sealed tube3616 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.808, Tmax = 0.876k = −16→16
14954 measured reflectionsl = −23→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.0418P)2] where P = (Fo2 + 2Fc2)/3
7631 reflections(Δ/σ)max < 0.001
408 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = −0.37 e Å3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
xyzUiso*/Ueq
Ni10.82715 (7)0.22869 (4)0.39454 (3)0.04134 (16)
S10.73997 (14)0.35458 (7)0.46177 (6)0.0484 (3)
S20.76184 (16)0.10350 (7)0.48848 (6)0.0547 (3)
S30.87246 (15)0.35324 (8)0.29580 (6)0.0528 (3)
S40.93428 (17)0.10088 (8)0.33202 (6)0.0613 (3)
C20.6768 (5)0.2822 (3)0.5502 (2)0.0441 (9)
C10.6135 (6)0.3411 (3)0.6099 (2)0.0499 (10)
C30.6833 (5)0.1733 (3)0.5608 (2)0.0440 (10)
C40.6232 (6)0.1130 (3)0.6311 (2)0.0551 (11)
C60.9759 (5)0.2797 (3)0.2284 (2)0.0465 (10)
C51.0367 (6)0.3382 (3)0.1563 (2)0.0565 (12)
C71.0008 (5)0.1697 (3)0.2436 (2)0.0479 (10)
C81.0813 (6)0.1076 (3)0.1876 (2)0.0558 (11)
C90.2604 (6)0.3605 (3)0.4593 (3)0.0606 (12)
H90.28700.42310.42730.073*
C100.1955 (5)0.3644 (3)0.5330 (3)0.0576 (12)
H100.17720.43010.54970.069*
C110.1563 (5)0.2723 (3)0.5835 (2)0.0461 (10)
C120.1837 (6)0.1787 (3)0.5540 (2)0.0577 (12)
H120.15940.11480.58500.069*
C130.2461 (6)0.1784 (3)0.4801 (3)0.0609 (12)
H130.26150.11400.46180.073*
C140.0815 (5)0.2768 (3)0.6632 (2)0.0481 (10)
C150.0630 (6)0.3698 (3)0.6932 (3)0.0672 (13)
H150.10120.43160.66450.081*
C16−0.0124 (6)0.3709 (4)0.7661 (3)0.0713 (14)
H16−0.02150.43450.78490.086*
C17−0.0516 (7)0.1977 (4)0.7814 (3)0.0785 (15)
H17−0.08910.13680.81170.094*
C180.0220 (6)0.1890 (3)0.7087 (3)0.0645 (13)
H180.03090.12440.69110.077*
C190.3576 (6)0.2552 (4)0.3530 (2)0.0682 (13)
H19A0.47850.21260.35660.082*
H19B0.27950.21590.33120.082*
C200.3667 (7)0.3600 (4)0.3003 (3)0.0956 (17)
H20A0.25070.40570.30060.143*
H20B0.39720.34760.24910.143*
H20C0.45820.39430.31700.143*
C210.2644 (6)0.2746 (4)0.9515 (3)0.0754 (14)
H210.21030.31360.98830.090*
C220.2539 (6)0.1671 (4)0.9611 (2)0.0686 (13)
H220.19190.13451.00400.082*
C230.3346 (5)0.1053 (4)0.9076 (2)0.0567 (11)
C240.4248 (6)0.1605 (4)0.8456 (2)0.0688 (13)
H240.48230.12310.80850.083*
C250.4311 (7)0.2679 (4)0.8376 (3)0.0796 (15)
H250.49170.30270.79510.095*
C260.3254 (6)−0.0126 (4)0.9179 (2)0.0572 (11)
C270.2592 (6)−0.0700 (4)0.9857 (3)0.0676 (13)
H270.2166−0.03591.02640.081*
C280.2581 (6)−0.1785 (4)0.9909 (3)0.0759 (14)
H280.2132−0.21551.03670.091*
C290.3719 (8)−0.1787 (5)0.8721 (3)0.0989 (19)
H290.4079−0.21510.83180.119*
C300.3822 (7)−0.0688 (4)0.8589 (3)0.0785 (15)
H300.4259−0.03410.81210.094*
C310.3614 (8)0.4438 (4)0.8812 (3)0.0931 (17)
H31A0.33670.47880.82840.112*
H31B0.26890.47650.91400.112*
C320.5411 (9)0.4616 (4)0.9009 (4)0.120 (2)
H32A0.57150.42090.95120.181*
H32B0.53830.53700.90050.181*
H32C0.63080.43860.86400.181*
N10.5638 (5)0.3873 (3)0.6585 (2)0.0711 (11)
N20.5710 (6)0.0624 (3)0.6863 (2)0.0819 (13)
N31.0878 (6)0.3863 (3)0.1002 (2)0.0855 (13)
N41.1447 (6)0.0573 (3)0.1433 (2)0.0788 (13)
N50.2860 (4)0.2673 (3)0.4330 (2)0.0513 (9)
N6−0.0723 (5)0.2883 (3)0.8109 (2)0.0716 (11)
N70.3506 (5)0.3244 (3)0.8906 (2)0.0708 (11)
N80.3154 (6)−0.2354 (4)0.9367 (3)0.0889 (13)
U11U22U33U12U13U23
Ni10.0509 (3)0.0353 (3)0.0370 (3)−0.0089 (2)0.0064 (2)−0.0055 (2)
S10.0639 (7)0.0369 (5)0.0446 (6)−0.0108 (5)0.0060 (5)−0.0085 (4)
S20.0809 (8)0.0356 (6)0.0452 (7)−0.0104 (5)0.0182 (6)−0.0072 (5)
S30.0705 (8)0.0391 (6)0.0450 (7)−0.0087 (5)0.0151 (6)−0.0043 (5)
S40.0992 (10)0.0382 (6)0.0447 (7)−0.0145 (6)0.0226 (6)−0.0081 (5)
C20.045 (2)0.046 (2)0.041 (2)−0.0056 (18)0.0023 (19)−0.0091 (18)
C10.055 (3)0.049 (2)0.045 (3)−0.006 (2)0.001 (2)−0.009 (2)
C30.051 (3)0.041 (2)0.037 (2)−0.0031 (19)0.0066 (19)−0.0056 (18)
C40.069 (3)0.048 (2)0.045 (3)−0.005 (2)0.014 (2)−0.009 (2)
C60.054 (3)0.049 (2)0.034 (2)−0.009 (2)0.003 (2)−0.0032 (18)
C50.077 (3)0.048 (3)0.043 (3)−0.008 (2)0.010 (2)−0.010 (2)
C70.065 (3)0.044 (2)0.036 (2)−0.010 (2)0.009 (2)−0.0108 (18)
C80.079 (3)0.050 (3)0.035 (3)−0.012 (2)0.002 (2)0.000 (2)
C90.064 (3)0.047 (3)0.070 (3)−0.015 (2)−0.001 (3)−0.004 (2)
C100.066 (3)0.035 (2)0.074 (3)−0.014 (2)0.003 (3)−0.011 (2)
C110.047 (2)0.035 (2)0.057 (3)−0.0102 (18)−0.007 (2)−0.0064 (19)
C120.075 (3)0.040 (2)0.059 (3)−0.015 (2)0.002 (3)−0.007 (2)
C130.077 (3)0.046 (3)0.061 (3)−0.012 (2)0.002 (3)−0.011 (2)
C140.045 (2)0.041 (2)0.058 (3)−0.0047 (19)0.000 (2)−0.011 (2)
C150.086 (4)0.048 (3)0.070 (3)−0.014 (2)0.012 (3)−0.018 (2)
C160.089 (4)0.054 (3)0.075 (4)−0.016 (3)0.004 (3)−0.021 (3)
C170.101 (4)0.057 (3)0.076 (4)−0.019 (3)0.014 (3)−0.008 (3)
C180.083 (3)0.046 (3)0.064 (3)−0.013 (2)0.003 (3)−0.009 (2)
C190.056 (3)0.092 (4)0.053 (3)−0.020 (3)−0.005 (2)0.005 (3)
C200.098 (4)0.098 (4)0.093 (4)−0.020 (3)0.003 (3)−0.021 (4)
C210.083 (4)0.089 (4)0.047 (3)−0.003 (3)0.016 (3)−0.010 (3)
C220.078 (3)0.080 (3)0.041 (3)−0.007 (3)0.017 (2)−0.007 (2)
C230.049 (3)0.075 (3)0.042 (3)−0.002 (2)0.002 (2)−0.009 (2)
C240.086 (4)0.077 (3)0.043 (3)−0.016 (3)0.017 (3)−0.012 (2)
C250.090 (4)0.088 (4)0.054 (3)−0.013 (3)0.020 (3)−0.007 (3)
C260.049 (3)0.081 (3)0.041 (3)−0.010 (2)0.003 (2)−0.013 (2)
C270.066 (3)0.085 (4)0.049 (3)−0.014 (3)0.012 (2)−0.008 (3)
C280.071 (4)0.090 (4)0.064 (4)−0.018 (3)0.001 (3)−0.007 (3)
C290.121 (5)0.095 (4)0.086 (4)−0.027 (4)0.033 (4)−0.031 (4)
C300.100 (4)0.082 (4)0.053 (3)−0.017 (3)0.022 (3)−0.017 (3)
C310.109 (5)0.070 (4)0.084 (4)0.010 (3)−0.003 (4)0.005 (3)
C320.144 (6)0.083 (4)0.137 (6)−0.017 (4)−0.003 (5)−0.026 (4)
N10.094 (3)0.067 (3)0.054 (3)−0.006 (2)0.009 (2)−0.026 (2)
N20.112 (3)0.075 (3)0.051 (3)−0.016 (2)0.025 (2)−0.001 (2)
N30.124 (4)0.074 (3)0.053 (3)−0.024 (3)0.029 (3)−0.001 (2)
N40.123 (4)0.062 (3)0.052 (3)−0.014 (2)0.023 (2)−0.021 (2)
N50.046 (2)0.047 (2)0.060 (2)−0.0098 (17)−0.0047 (18)−0.0043 (18)
N60.088 (3)0.062 (3)0.068 (3)−0.011 (2)0.006 (2)−0.020 (2)
N70.078 (3)0.073 (3)0.052 (3)0.001 (2)0.005 (2)−0.003 (2)
N80.101 (4)0.087 (3)0.080 (3)−0.022 (3)0.013 (3)−0.018 (3)
Ni1—S12.1796 (11)C17—H170.9300
Ni1—S22.1668 (11)C18—H180.9300
Ni1—S42.1703 (11)C19—C201.485 (6)
Ni1—S32.1760 (11)C19—N51.515 (5)
S1—C21.740 (4)C19—H19A0.9700
S2—C31.723 (4)C19—H19B0.9700
S3—C61.731 (4)C20—H20A0.9600
S4—C71.730 (4)C20—H20B0.9600
C2—C31.362 (5)C20—H20C0.9600
C2—C11.431 (5)C21—N71.331 (5)
C1—N11.149 (4)C21—C221.367 (6)
C3—C41.422 (5)C21—H210.9300
C4—N21.148 (5)C22—C231.398 (5)
C6—C71.362 (5)C22—H220.9300
C6—C51.440 (5)C23—C241.388 (5)
C5—N31.143 (5)C23—C261.496 (6)
C7—C81.434 (5)C24—C251.362 (6)
C8—N41.145 (5)C24—H240.9300
C9—N51.346 (5)C25—N71.350 (5)
C9—C101.374 (5)C25—H250.9300
C9—H90.9300C26—C271.390 (5)
C10—C111.395 (5)C26—C301.390 (5)
C10—H100.9300C27—C281.374 (6)
C11—C121.378 (5)C27—H270.9300
C11—C141.498 (5)C28—N81.326 (5)
C12—C131.366 (5)C28—H280.9300
C12—H120.9300C29—N81.317 (6)
C13—N51.338 (5)C29—C301.394 (6)
C13—H130.9300C29—H290.9300
C14—C181.370 (5)C30—H300.9300
C14—C151.379 (5)C31—C321.468 (7)
C15—C161.380 (6)C31—N71.519 (6)
C15—H150.9300C31—H31A0.9700
C16—N61.316 (5)C31—H31B0.9700
C16—H160.9300C32—H32A0.9600
C17—N61.346 (5)C32—H32B0.9600
C17—C181.388 (6)C32—H32C0.9600
S2—Ni1—S487.25 (4)C20—C19—H19B108.9
S2—Ni1—S3175.30 (5)N5—C19—H19B108.9
S4—Ni1—S391.97 (4)H19A—C19—H19B107.7
S2—Ni1—S192.18 (4)C19—C20—H20A109.5
S4—Ni1—S1175.51 (5)C19—C20—H20B109.5
S3—Ni1—S188.96 (4)H20A—C20—H20B109.5
C2—S1—Ni1102.87 (13)C19—C20—H20C109.5
C3—S2—Ni1103.49 (13)H20A—C20—H20C109.5
C6—S3—Ni1103.08 (13)H20B—C20—H20C109.5
C7—S4—Ni1103.58 (13)N7—C21—C22121.2 (4)
C3—C2—C1121.6 (3)N7—C21—H21119.4
C3—C2—S1120.4 (3)C22—C21—H21119.4
C1—C2—S1117.9 (3)C21—C22—C23121.3 (4)
N1—C1—C2179.2 (5)C21—C22—H22119.4
C2—C3—C4121.5 (3)C23—C22—H22119.4
C2—C3—S2121.0 (3)C24—C23—C22115.5 (4)
C4—C3—S2117.5 (3)C24—C23—C26122.8 (4)
N2—C4—C3177.3 (5)C22—C23—C26121.7 (4)
C7—C6—C5121.0 (3)C25—C24—C23121.6 (4)
C7—C6—S3121.0 (3)C25—C24—H24119.2
C5—C6—S3118.0 (3)C23—C24—H24119.2
N3—C5—C6177.9 (5)N7—C25—C24120.8 (5)
C6—C7—C8121.7 (3)N7—C25—H25119.6
C6—C7—S4120.3 (3)C24—C25—H25119.6
C8—C7—S4118.0 (3)C27—C26—C30117.4 (4)
N4—C8—C7179.4 (5)C27—C26—C23122.0 (4)
N5—C9—C10120.8 (4)C30—C26—C23120.6 (4)
N5—C9—H9119.6C28—C27—C26118.4 (5)
C10—C9—H9119.6C28—C27—H27120.8
C9—C10—C11121.6 (4)C26—C27—H27120.8
C9—C10—H10119.2N8—C28—C27125.9 (5)
C11—C10—H10119.2N8—C28—H28117.0
C12—C11—C10115.7 (4)C27—C28—H28117.0
C12—C11—C14122.7 (3)N8—C29—C30125.5 (5)
C10—C11—C14121.6 (3)N8—C29—H29117.3
C13—C12—C11121.0 (4)C30—C29—H29117.3
C13—C12—H12119.5C26—C30—C29118.0 (5)
C11—C12—H12119.5C26—C30—H30121.0
N5—C13—C12122.4 (4)C29—C30—H30121.0
N5—C13—H13118.8C32—C31—N7111.8 (4)
C12—C13—H13118.8C32—C31—H31A109.3
C18—C14—C15117.0 (4)N7—C31—H31A109.3
C18—C14—C11120.9 (4)C32—C31—H31B109.3
C15—C14—C11122.0 (4)N7—C31—H31B109.3
C14—C15—C16119.7 (4)H31A—C31—H31B107.9
C14—C15—H15120.1C31—C32—H32A109.5
C16—C15—H15120.1C31—C32—H32B109.5
N6—C16—C15124.8 (4)H32A—C32—H32B109.5
N6—C16—H16117.6C31—C32—H32C109.5
C15—C16—H16117.6H32A—C32—H32C109.5
N6—C17—C18124.4 (4)H32B—C32—H32C109.5
N6—C17—H17117.8C13—N5—C9118.5 (4)
C18—C17—H17117.8C13—N5—C19117.0 (3)
C14—C18—C17119.1 (4)C9—N5—C19124.5 (4)
C14—C18—H18120.5C16—N6—C17114.9 (4)
C17—C18—H18120.5C21—N7—C25119.6 (4)
C20—C19—N5113.4 (4)C21—N7—C31120.4 (4)
C20—C19—H19A108.9C25—N7—C31120.0 (4)
N5—C19—H19A108.9C29—N8—C28114.7 (5)
D—H···AD—HH···AD···AD—H···A
C13—H13···S2i0.932.783.549 (4)141
C17—H17···N4i0.932.553.441 (6)161
C21—H21···N3ii0.932.423.342 (6)170
C22—H22···N4ii0.932.503.372 (5)156
C24—H24···N20.932.463.364 (5)163
C25—H25···N10.932.523.411 (6)161
C27—H27···N4ii0.932.583.498 (6)172
C30—H30···N20.932.603.526 (6)176
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A DA D—H⋯A
C13—H13⋯S2i 0.932.783.549 (4)141
C17—H17⋯N4i 0.932.553.441 (6)161
C21—H21⋯N3ii 0.932.423.342 (6)170
C22—H22⋯N4ii 0.932.503.372 (5)156
C24—H24⋯N20.932.463.364 (5)163
C25—H25⋯N10.932.523.411 (6)161
C27—H27⋯N4ii 0.932.583.498 (6)172
C30—H30⋯N20.932.603.526 (6)176

Symmetry codes: (i) ; (ii) .

  4 in total

1.  Conducting metal dithiolene complexes: structural and electronic properties.

Authors:  Reizo Kato
Journal:  Chem Rev       Date:  2004-11       Impact factor: 60.622

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  A low-dimensional molecular spin system with two steps of magnetic transitions and liquid crystal property.

Authors:  Hai-Bao Duan; Xiao-Ming Ren; Lin-Jiang Shen; Wan-Qin Jin; Qing-Jin Meng; Zheng-Fang Tian; Shi-Ming Zhou
Journal:  Dalton Trans       Date:  2011-03-04       Impact factor: 4.390

4.  Ion-pair complexes with strong near infrared absorbance: syntheses, crystal structures and spectroscopic properties.

Authors:  Wen-Bo Pei; Jian-Sheng Wu; Jian-Lan Liu; Xiao-Ming Ren; Lin-Jiang Shen
Journal:  Spectrochim Acta A Mol Biomol Spectrosc       Date:  2009-10-20       Impact factor: 4.098

  4 in total

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