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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page m10
https://doi.org/10.1107/S1600536807062101

Di­chlorido(di-2-pyridyl sulfide-κ2N,N′)zinc(II)

Mario Wriedt,a* Inke Jessa and Christian Näthera

aInstitut für Anorganische Chemie, Christian-Albrechts-Universität Kiel, Olshausenstrasse 40, D-24098 Kiel, Germany
*Correspondence e-mail: mwriedt@ac.uni-kiel.de

(Received 21 November 2007; accepted 22 November 2007; online 6 December 2007)

The crystal structure of the title compound, [ZnCl2(C10H8N2S)], consists of a six-membered chelate ring in which the Zn atom is approximately tetra­hedrally coordinated by two chloride ions and by the two pyridyl N atoms of a single di-2-pyridyl sulfide ligand. As usual for this type of complex, the sulfide group does not participate in zinc coordination. The dihedral angle between the two pyridine rings is 50.4 (1)°.

Related literature

For related literature, see: Anderson & Steel (1998[Anderson, R. J. & Steel, P. J. (1998). Acta Cryst. C54, 223-225.]); Bhosekar et al. (2007[Bhosekar, G., Jess, I. & Näther, C. (2007). Inorg. Chem. 43, 6508-6515.]); Kondo et al. (1995[Kondo, M., Kawata, S., Kitagawa, S., Kiso, H. & Munakata, M. (1995). Acta Cryst. C51, 567-569.]); Nicolò et al. (1996[Nicolò, F., Bruno, G. & Tresoldi, G. (1996). Acta Cryst. C52, 2188-2191.]); Teles et al. (1999[Teles, W. M., Fernandes, N. G., Abras, A. & Filgueiras, C. A. L. (1999). Transition Met. Chem. 24, 321-325.]); Tresoldi et al. (1991[Tresoldi, G., Piraino, P., Rotondo, E. & Faraone, F. (1991). J. Chem. Soc. Dalton Trans., pp. 425-430.], 1992[Tresoldi, G., Rotondo, E., Piraino, P., Lanfranchi, M. & Tiripichio, A. (1992). Inorg. Chim. Acta, 194, 233-241.]).

[Scheme 1]

Experimental

Crystal data

  • [ZnCl2(C10H8N2S)]

  • Mr = 324.51

  • Monoclinic, P 21 /c

  • a = 12.1944 (12) Å

  • b = 7.6404 (4) Å

  • c = 14.2572 (15) Å

  • β = 110.426 (12)°

  • V = 1244.82 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.54 mm−1

  • T = 170 (2) K

  • 0.14 × 0.10 × 0.07 mm
Data collection

  • Stoe IPDSI diffractometer

  • Absorption correction: numerical (X-SHAPE; Stoe & Cie, 1998[Stoe & Cie (1998). X-SHAPE (Version 1.03) and IPDS Program Package (Version 2.89). Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.751, Tmax = 0.852

  • 7272 measured reflections

  • 2939 independent reflections

  • 2297 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.096

  • S = 1.00

  • 2939 reflections

  • 146 parameters

  • H-atom parameters constrained

  • Δρmax = 0.47 e Å−3

  • Δρmin = −0.60 e Å−3

Table 1
Selected geometric parameters (Å, °)

Zn1—N1 2.057 (2)
Zn1—N11 2.061 (2)
Zn1—Cl1 2.2192 (8)
Zn1—Cl2 2.2261 (8)
N1—Zn1—Cl1 109.32 (7)
N11—Zn1—Cl1 115.66 (7)
N1—Zn1—Cl2 108.68 (7)
N11—Zn1—Cl2 107.42 (7)

Data collection: IPDS Program Package (Stoe & Cie, 1998[Stoe & Cie (1998). X-SHAPE (Version 1.03) and IPDS Program Package (Version 2.89). Stoe & Cie, Darmstadt, Germany.]); cell refinement: IPDS Program Package; data reduction: IPDS Program Package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: XP in SHELXTL (Bruker, 1998[Bruker (1998). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: CIFTAB in SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807062101/bt2646sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062101/bt2646Isup2.hkl

checkCIF report


Comment top

Recently, we are interested in the synthesis, structures and thermal properties of coordination polymers based on zinc(II) halides and N-donor ligands (Bhosekar et al., 2007). We have found for example that most of the ligand rich compounds can be transformed into ligand deficient compounds on heating. Starting from these findings we have initiated systematic investigations on this topic. In these investigations we have reacted zinc(II) chloride with 2,2'-bipyridyldisulfide. In this reaction, simultaneously a cleavage of the S—S bond takes place leading to the formation of di-2-pyridyl sulfide (dps). In further reaction with zinc(II) chloride the title compound (I) is formed. To identify this product in further reaction by X-ray powder diffraction, a structure determination was performed.

In general dps is a versatile ambidentate ligand that, due to its conformational flexibility, can act in N,N'-bidentate (Tresoldi et al., 1992; Kondo et al., 1995 and Nicolò et al., 1996) or bridging (Tresoldi et al., 1991 and Teles et al., 1999) coordination modes toward many metals, resulting in complexes with different stereochemistry. When dps is bonded to the metal as a chelate ligand, a six-membered ring in boat conformation is formed, differently from its rigid analogues 2,2'-bipyridine that generates a pentacyclic chelate in a planar arragement. In addition, in some cases dps can act as tridentate ligand in a N,N,S-coordination mode involving metal-sulfur interactions (Anderson & Steel, 1998).

In the crystal structure the coordination geometry about the Zn(II) ion is approximately tetrahedral with bonds being formed to two chloride ions and the two pyridyl nitrogen atoms of a single dps ligand (Fig. 1). These latter interactions result in the formation of a six-membered chelate ring, which is in a boat conformation. The angles at Zn(II) range from 93.85 to 115.66°, the largest being N—Zn—Cl. The Zn—Cl and Zn—N distances are in the range of 2.057 (2)–2.061 (2) and 2.2192 (8)–2.2261 (8) Å. The structural parameters in the dps molecule are quite regular. In particular the C—S bonds, 1.782 (3) and 1.780 (3) Å, are in good agreement with those expected for C(sp2)-S bonds (1.77 Å).

Related literature top

For related literature, see: Anderson & Steel (1998); Bhosekar et al. (2007); Kondo et al. (1995); Nicolò et al. (1996); Teles et al. (1999); Tresoldi et al. (1991, 1992).

Experimental top

ZnCl2 and 2,2'-bipyridyldisulfide was obtained from Alfa Aesar and methanol was obtained from Fluka. 0.0313 mmol (4.3 mg) zinc(II) chloride, 0.125 mmol (27.5 mg) 2,2'-bipyridyldisulfide and 3 ml of methanol were transfered in test-tube, which were closed and heated to 110 °C for three days. On cooling colourless block-shaped single crystals of (I) are obtained.

Refinement top

All H atoms were located in difference map but were positioned with idealized geometry and were refined isotropic with Ueq(H) = 1.2Ueq(C) of the parent atom using a riding model with C—H = 0.97 Å.

Structure description top

Recently, we are interested in the synthesis, structures and thermal properties of coordination polymers based on zinc(II) halides and N-donor ligands (Bhosekar et al., 2007). We have found for example that most of the ligand rich compounds can be transformed into ligand deficient compounds on heating. Starting from these findings we have initiated systematic investigations on this topic. In these investigations we have reacted zinc(II) chloride with 2,2'-bipyridyldisulfide. In this reaction, simultaneously a cleavage of the S—S bond takes place leading to the formation of di-2-pyridyl sulfide (dps). In further reaction with zinc(II) chloride the title compound (I) is formed. To identify this product in further reaction by X-ray powder diffraction, a structure determination was performed.

In general dps is a versatile ambidentate ligand that, due to its conformational flexibility, can act in N,N'-bidentate (Tresoldi et al., 1992; Kondo et al., 1995 and Nicolò et al., 1996) or bridging (Tresoldi et al., 1991 and Teles et al., 1999) coordination modes toward many metals, resulting in complexes with different stereochemistry. When dps is bonded to the metal as a chelate ligand, a six-membered ring in boat conformation is formed, differently from its rigid analogues 2,2'-bipyridine that generates a pentacyclic chelate in a planar arragement. In addition, in some cases dps can act as tridentate ligand in a N,N,S-coordination mode involving metal-sulfur interactions (Anderson & Steel, 1998).

In the crystal structure the coordination geometry about the Zn(II) ion is approximately tetrahedral with bonds being formed to two chloride ions and the two pyridyl nitrogen atoms of a single dps ligand (Fig. 1). These latter interactions result in the formation of a six-membered chelate ring, which is in a boat conformation. The angles at Zn(II) range from 93.85 to 115.66°, the largest being N—Zn—Cl. The Zn—Cl and Zn—N distances are in the range of 2.057 (2)–2.061 (2) and 2.2192 (8)–2.2261 (8) Å. The structural parameters in the dps molecule are quite regular. In particular the C—S bonds, 1.782 (3) and 1.780 (3) Å, are in good agreement with those expected for C(sp2)-S bonds (1.77 Å).

For related literature, see: Anderson & Steel (1998); Bhosekar et al. (2007); Kondo et al. (1995); Nicolò et al. (1996); Teles et al. (1999); Tresoldi et al. (1991, 1992).

Computing details top

Data collection: IPDS Program Package (Stoe & Cie, 1998); cell refinement: IPDS Program Package (Stoe & Cie, 1998); data reduction: IPDS Program Package (Stoe & Cie, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: CIFTAB in SHELXTL (Bruker, 1998).

Figures top
[Figure 1] Fig. 1. : Crystal structure of compound I with labelling and displacement ellipsoids drawn at the 50% probability level.
Dichlorido(di-2-pyridyl sulfide-κ2N,N')zinc(II) top
Crystal data top
[ZnCl2(C10H8N2S)]F(000) = 648
Mr = 324.51Dx = 1.732 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.1944 (12) ÅCell parameters from 7174 reflections
b = 7.6404 (4) Åθ = 3–28.1°
c = 14.2572 (15) ŵ = 2.54 mm−1
β = 110.426 (12)°T = 170 K
V = 1244.82 (19) Å3Block, colourless
Z = 40.14 × 0.10 × 0.07 mm
Data collection top
Stoe IPDSI
diffractometer		2939 independent reflections
Radiation source: fine-focus sealed tube2297 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Phi scansθmax = 28.1°, θmin = 3.0°
Absorption correction: numerical
(X-SHAPE; Stoe & Cie, 1998)		h = −16→15
Tmin = 0.751, Tmax = 0.852k = −8→10
7272 measured reflectionsl = −15→18
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0636P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2939 reflectionsΔρmax = 0.47 e Å−3
146 parametersΔρmin = −0.60 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0121 (14)
Crystal data top
[ZnCl2(C10H8N2S)]V = 1244.82 (19) Å3
Mr = 324.51Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.1944 (12) ŵ = 2.54 mm−1
b = 7.6404 (4) ÅT = 170 K
c = 14.2572 (15) Å0.14 × 0.10 × 0.07 mm
β = 110.426 (12)°
Data collection top
Stoe IPDSI
diffractometer		2939 independent reflections
Absorption correction: numerical
(X-SHAPE; Stoe & Cie, 1998)		2297 reflections with I > 2σ(I)
Tmin = 0.751, Tmax = 0.852Rint = 0.036
7272 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.096H-atom parameters constrained
S = 1.00Δρmax = 0.47 e Å−3
2939 reflectionsΔρmin = −0.60 e Å−3
146 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
xyzUiso*/Ueq
Zn10.75122 (3)0.38978 (4)0.21941 (2)0.02084 (13)
Cl10.85027 (6)0.14097 (10)0.23692 (6)0.02808 (18)
Cl20.71512 (7)0.54386 (11)0.07932 (6)0.03121 (19)
N110.59754 (19)0.3765 (3)0.24881 (19)0.0218 (5)
C110.5996 (2)0.3642 (4)0.3433 (2)0.0225 (6)
C120.4973 (3)0.3575 (4)0.3656 (3)0.0304 (7)
H120.50070.34580.43290.036*
C130.3906 (3)0.3682 (4)0.2884 (3)0.0346 (8)
H130.31980.36260.30210.042*
C140.3878 (3)0.3870 (4)0.1910 (3)0.0329 (7)
H140.31540.39700.13710.039*
C150.4925 (2)0.3910 (4)0.1739 (2)0.0272 (6)
H150.49090.40440.10720.033*
N10.83245 (18)0.5499 (3)0.33969 (18)0.0202 (5)
C10.8192 (2)0.5231 (4)0.4286 (2)0.0214 (5)
C20.8775 (2)0.6216 (4)0.5128 (2)0.0250 (6)
H20.86540.60150.57420.030*
C30.9546 (2)0.7517 (4)0.5049 (2)0.0289 (7)
H30.99740.81940.56180.035*
C40.9679 (2)0.7808 (4)0.4139 (3)0.0292 (6)
H41.01990.86840.40710.035*
C50.9039 (2)0.6795 (4)0.3328 (2)0.0229 (6)
H50.91070.70250.26960.027*
S10.73529 (6)0.34212 (11)0.44428 (6)0.02965 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02206 (18)0.0255 (2)0.01652 (18)−0.00095 (12)0.00868 (12)−0.00111 (13)
Cl10.0294 (3)0.0284 (4)0.0268 (4)0.0042 (3)0.0101 (3)−0.0009 (3)
Cl20.0438 (4)0.0333 (4)0.0195 (4)0.0018 (3)0.0148 (3)0.0042 (3)
N110.0207 (10)0.0244 (12)0.0216 (12)−0.0007 (9)0.0090 (9)0.0001 (10)
C110.0245 (12)0.0212 (14)0.0248 (14)−0.0028 (10)0.0123 (11)0.0008 (11)
C120.0327 (15)0.0324 (17)0.0335 (17)−0.0010 (12)0.0210 (13)0.0041 (14)
C130.0250 (14)0.0336 (18)0.050 (2)−0.0013 (12)0.0196 (14)0.0035 (15)
C140.0227 (13)0.0330 (17)0.0390 (19)−0.0019 (12)0.0056 (13)0.0073 (15)
C150.0246 (13)0.0304 (16)0.0240 (15)−0.0021 (11)0.0053 (11)0.0035 (13)
N10.0213 (10)0.0208 (12)0.0186 (11)0.0014 (9)0.0072 (9)0.0003 (9)
C10.0229 (12)0.0239 (14)0.0176 (13)0.0042 (10)0.0075 (10)0.0009 (11)
C20.0286 (13)0.0290 (16)0.0161 (13)0.0099 (11)0.0060 (11)−0.0001 (12)
C30.0328 (15)0.0212 (15)0.0255 (15)0.0056 (11)0.0011 (12)−0.0086 (12)
C40.0284 (14)0.0204 (14)0.0350 (17)−0.0009 (11)0.0064 (12)−0.0025 (13)
C50.0237 (13)0.0219 (14)0.0230 (14)0.0012 (10)0.0081 (11)0.0033 (12)
S10.0296 (4)0.0375 (4)0.0206 (4)−0.0047 (3)0.0073 (3)0.0094 (3)
Geometric parameters (Å, º) top
Zn1—N12.057 (2)C14—H140.9500
Zn1—N112.061 (2)C15—H150.9500
Zn1—Cl12.2192 (8)N1—C51.345 (4)
Zn1—Cl22.2261 (8)N1—C11.349 (4)
N11—C111.342 (4)C1—C21.384 (4)
N11—C151.355 (4)C1—S11.780 (3)
C11—C121.392 (4)C2—C31.399 (4)
C11—S11.782 (3)C2—H20.9500
C12—C131.382 (5)C3—C41.381 (5)
C12—H120.9500C3—H30.9500
C13—C141.384 (5)C4—C51.384 (4)
C13—H130.9500C4—H40.9500
C14—C151.382 (4)C5—H50.9500
N1—Zn1—N1193.85 (9)N11—C15—H15118.8
N1—Zn1—Cl1109.32 (7)C14—C15—H15118.8
N11—Zn1—Cl1115.66 (7)C5—N1—C1118.3 (3)
N1—Zn1—Cl2108.68 (7)C5—N1—Zn1120.83 (19)
N11—Zn1—Cl2107.42 (7)C1—N1—Zn1120.83 (19)
Cl1—Zn1—Cl2118.90 (3)N1—C1—C2122.6 (3)
C11—N11—C15118.5 (2)N1—C1—S1119.9 (2)
C11—N11—Zn1120.53 (18)C2—C1—S1117.2 (2)
C15—N11—Zn1120.8 (2)C1—C2—C3118.2 (3)
N11—C11—C12121.8 (3)C1—C2—H2120.9
N11—C11—S1120.3 (2)C3—C2—H2120.9
C12—C11—S1117.7 (2)C4—C3—C2119.5 (3)
C13—C12—C11119.1 (3)C4—C3—H3120.2
C13—C12—H12120.5C2—C3—H3120.2
C11—C12—H12120.5C3—C4—C5118.5 (3)
C12—C13—C14119.5 (3)C3—C4—H4120.7
C12—C13—H13120.3C5—C4—H4120.7
C14—C13—H13120.3N1—C5—C4122.8 (3)
C15—C14—C13118.5 (3)N1—C5—H5118.6
C15—C14—H14120.7C4—C5—H5118.6
C13—C14—H14120.7C1—S1—C11103.75 (13)
N11—C15—C14122.5 (3)

Experimental details

Crystal data
Chemical formula[ZnCl2(C10H8N2S)]
Mr324.51
Crystal system, space groupMonoclinic, P21/c
Temperature (K)170
a, b, c (Å)12.1944 (12), 7.6404 (4), 14.2572 (15)
β (°) 110.426 (12)
V (Å3)1244.82 (19)
Z4
Radiation typeMo Kα
µ (mm−1)2.54
Crystal size (mm)0.14 × 0.10 × 0.07
Data collection
DiffractometerStoe IPDSI
Absorption correctionNumerical
(X-SHAPE; Stoe & Cie, 1998)
Tmin, Tmax0.751, 0.852
No. of measured, independent and
observed [I > 2σ(I)] reflections		7272, 2939, 2297
Rint0.036
(sin θ/λ)max (Å−1)0.664
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.096, 1.00
No. of reflections2939
No. of parameters146
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.47, −0.60

Computer programs: IPDS Program Package (Stoe & Cie, 1998), SHELXS97 (Sheldrick, 1997, SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1998), CIFTAB in SHELXTL (Bruker, 1998).

Selected geometric parameters (Å, º) top
Zn1—N12.057 (2)Zn1—Cl22.2261 (8)
Zn1—N112.061 (2)C11—S11.782 (3)
Zn1—Cl12.2192 (8)C1—S11.780 (3)
N1—Zn1—Cl1109.32 (7)N1—Zn1—Cl2108.68 (7)
N11—Zn1—Cl1115.66 (7)N11—Zn1—Cl2107.42 (7)
 

Acknowledgements

This work is supported by the state of Schleswig-Holstein and the Deutsche Forschungsgemeinschaft (Projekt No. NA 720/1–1). We are very grateful to Professor Dr. Wolfgang Bensch for the facility to use his experimental equipment.

References

First citationAnderson, R. J. & Steel, P. J. (1998). Acta Cryst. C54, 223–225.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationBhosekar, G., Jess, I. & Näther, C. (2007). Inorg. Chem. 43, 6508–6515.  Google Scholar
 First citationBruker (1998). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationKondo, M., Kawata, S., Kitagawa, S., Kiso, H. & Munakata, M. (1995). Acta Cryst. C51, 567–569.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationNicolò, F., Bruno, G. & Tresoldi, G. (1996). Acta Cryst. C52, 2188–2191.  CSD CrossRef Web of Science IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationStoe & Cie (1998). X-SHAPE (Version 1.03) and IPDS Program Package (Version 2.89). Stoe & Cie, Darmstadt, Germany.  Google Scholar
 First citationTeles, W. M., Fernandes, N. G., Abras, A. & Filgueiras, C. A. L. (1999). Transition Met. Chem. 24, 321–325.  Web of Science CSD CrossRef CAS Google Scholar
 First citationTresoldi, G., Piraino, P., Rotondo, E. & Faraone, F. (1991). J. Chem. Soc. Dalton Trans., pp. 425-430.  Google Scholar
 First citationTresoldi, G., Rotondo, E., Piraino, P., Lanfranchi, M. & Tiripichio, A. (1992). Inorg. Chim. Acta, 194, 233–241.  CSD CrossRef CAS Web of Science Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page m10
https://doi.org/10.1107/S1600536807062101
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