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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 m83
https://doi.org/10.1107/S1600536807063556

Di­bromido(di-2-pyridyl di­sulfide-κ2N,N′)zinc(II)

Mario Wriedt,a* Inke Jessa and Christian Näthera

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

(Received 22 November 2007; accepted 26 November 2007; online 6 December 2007)

The molecular structure of the title compound, [ZnBr2(C10H8N2S2)], contains a seven-membered chelate ring in which the zinc atom is coordinated by two bromide ions and by the two pyridyl N atoms of a single 2,2′-dipyridyldisulfide (dpds) ligand within a slightly distorted tetra­hedron. As is usual for this type of complex, the disulfide group does not participate in zinc coordination. The chelate complexes are connected via weak inter­molecular C—H⋯Br hydrogen bonding into chains, which extend in the [010] direction.

Related literature

For related literature, see: Bhosekar et al. (2007[Bhosekar, G., Jess, I. & Näther, C. (2007). Inorg. Chem. 43, 6508-6515.]); Kinoshita et al. (2003[Kinoshita, I., Wright, L. J., Kubo, S., Kimura, K., Sakata, A., Yano, T., Miyamoto, R., Nishioka, T. & Isobe, K. (2003). Dalton Trans. pp. 1993-2003.]); Kadooka et al. (1976[Kadooka, M. M., Warner, L. G. & Seff, K. (1976). Inorg. Chem. 15, 4, 812-816.]); Kubo et al. (1998[Kubo, S., Nishioka, T., Ishikawa, K., Kinoshita, I. & Isobe, K. (1998). Chem. Lett. 27, 1067-1068.]); Näther & Jess (2006[Näther, C. & Jess, I. (2006). Inorg. Chem. 45, 7446-7454.]); Näther et al. (2003[Näther, C., Wriedt, M. & Jess, I. (2003). Inorg. Chem. 42, 2391-2397.]); Pickardt et al. (2005[Pickardt, J., von Chrzanowski, J., Steudel, R., Borowski, M. & Beck, S. (2005). Z. Naturforsch. Teil B, 60, 373-376.]); Raghavan & Seff (1977[Raghavan, N. V. & Seff, K. (1977). Acta Cryst. B33, 386-391.]).

[Scheme 1]

Experimental

Crystal data

  • [ZnBr2(C10H8N2S2)]

  • Mr = 445.49

  • Triclinic, [P \overline 1]

  • a = 7.7610 (8) Å

  • b = 8.2962 (8) Å

  • c = 12.3576 (13) Å

  • α = 95.488 (12)°

  • β = 107.161 (12)°

  • γ = 112.950 (11)°

  • V = 679.70 (12) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 7.97 mm−1

  • T = 170 (2) K

  • 0.09 × 0.09 × 0.08 mm
Data collection

  • Stoe IPDS-1 diffractometer

  • Absorption correction: none

  • 6076 measured reflections

  • 2609 independent reflections

  • 2167 reflections with I > 2σ(I)

  • Rint = 0.054
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.120

  • S = 1.06

  • 2609 reflections

  • 155 parameters

  • H-atom parameters constrained

  • Δρmax = 1.31 e Å−3

  • Δρmin = −1.43 e Å−3

Table 1
Selected geometric parameters (Å, °)

Br1—Zn1 2.3897 (10)
Br2—Zn1 2.3664 (10)
Zn1—N11 2.042 (5)
Zn1—N1 2.091 (5)
N11—Zn1—N1 117.2 (2)
N11—Zn1—Br2 112.77 (15)
N1—Zn1—Br2 103.61 (14)
N11—Zn1—Br1 103.35 (15)
N1—Zn1—Br1 100.99 (15)
Br2—Zn1—Br1 119.06 (4)

Data collection: IPDS Program Package (Stoe, 1998[Stoe (1998). 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, 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/S1600536807063556/si2061sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063556/si2061Isup2.hkl

checkCIF report


Comment top

In our ongoing investigation on the synthesis, structures and properties of new coordination polymers based on zinc(II) halides and N-donor ligands (Bhosekar et al. 2007), we have startet systematic investigation of their thermal behavior because we have demonstrated that new ligand-deficient coordination polymers can be conveniently prepared by thermal decompisition of suitable ligand-rich precursur compounds (Näther et al. 2003; Näther & Jess, 2006). In further investigations we have reacted zinc(II) bromine with 2,2'-bipyridyldisulfide (dpds). In this reaction the title chelate-complex has been formed by accident.

The versatile coordination properties of dpds enables a series of different chelate-complexes and coordination polymers. It can act in N,N'-bidentate (Kinoshita et al., 2003; Kadooka et al. 1976 & Pickardt et al. 2005) or bridging (Kubo et al. 1998 & Kinoshita et al. 2003) coordination modes toward many metals. When dpds is connected to the metal atom as a chelate ligand, a seven-membered ring is formed.

The title compound is isotypic to that of the corresponding chloride compound reported by Pickardt et al. in 2005. In the crystal structure the coordination geometry about the Zn(II) ion is almost tetrahedral with bonds being formed to two bromine ions and the two pyridyl nitrogen atoms of a single dpds ligand (Fig. 1). These latter interactions result in the formation of a seven-membered chelate ring. As usual for this type of complexes, the disulfide group does not participate in zinc-coordination. Moreover the chelate-complexes form infinite weak C—H···Br intermolecular hydrogen bonded chains along the [0 1 0] direction (C12—H12: 0.95 Å, H12···Br2i: 2.84 (2) Å, C12···Br2i: 3.74 (3), C12—H12···Bri: 160 °, see Fig. 2). The Zn—Br and Zn—N distances are in the range of 2.3664 (10)–2.3897 (10) and 2.042 (5)–2.091 (5) Å. The angles at Zn(II) range from 100.99 (15) to 119.06 (4)°, the largest being Br—Zn—Br (Tab. 1). The structural parameters in the dpds molecule are quite regular. In particular the C—S bond, 1.784 (7)–1.783 (6) Å, is in good agreement with those expected for C(sp2)—S bonds (1.77 Å). The S—S bond length, 2.050 (3) Å, is somewhat longer than that found in the structure of the free ligand, 2.016 (2) Å (Raghavan & Seff, 1977).

Related literature top

For related literature, see: Bhosekar et al. (2007); Kinoshita et al. (2003); Kadooka et al. (1976); Kubo et al. (1998); Näther & Jess (2006); Näther et al. (2003); Pickardt et al. (2005); Raghavan & Seff (1977).

Experimental top

ZnBr2 and dpds was obtained from Alfa Aesar and methanol was obtained from Fluka. 0.125 mmol (28.15 mg) zinc(II) bromine, 0.125 mmol (27.5 mg) dpds and 3 ml of methanol were transfered in a test-tube, which were closed and heated to 110 °C for four days. On cooling colourless block-shaped single crystals of (I) were obtained.

Refinement top

All H atoms were located in difference map but were positioned with idealized geometry and were refined isotropic with Ueq(H) = 1.2 Ueq(C) of the parent atom using a riding model with C—H = 0.95 Å.

Structure description top

In our ongoing investigation on the synthesis, structures and properties of new coordination polymers based on zinc(II) halides and N-donor ligands (Bhosekar et al. 2007), we have startet systematic investigation of their thermal behavior because we have demonstrated that new ligand-deficient coordination polymers can be conveniently prepared by thermal decompisition of suitable ligand-rich precursur compounds (Näther et al. 2003; Näther & Jess, 2006). In further investigations we have reacted zinc(II) bromine with 2,2'-bipyridyldisulfide (dpds). In this reaction the title chelate-complex has been formed by accident.

The versatile coordination properties of dpds enables a series of different chelate-complexes and coordination polymers. It can act in N,N'-bidentate (Kinoshita et al., 2003; Kadooka et al. 1976 & Pickardt et al. 2005) or bridging (Kubo et al. 1998 & Kinoshita et al. 2003) coordination modes toward many metals. When dpds is connected to the metal atom as a chelate ligand, a seven-membered ring is formed.

The title compound is isotypic to that of the corresponding chloride compound reported by Pickardt et al. in 2005. In the crystal structure the coordination geometry about the Zn(II) ion is almost tetrahedral with bonds being formed to two bromine ions and the two pyridyl nitrogen atoms of a single dpds ligand (Fig. 1). These latter interactions result in the formation of a seven-membered chelate ring. As usual for this type of complexes, the disulfide group does not participate in zinc-coordination. Moreover the chelate-complexes form infinite weak C—H···Br intermolecular hydrogen bonded chains along the [0 1 0] direction (C12—H12: 0.95 Å, H12···Br2i: 2.84 (2) Å, C12···Br2i: 3.74 (3), C12—H12···Bri: 160 °, see Fig. 2). The Zn—Br and Zn—N distances are in the range of 2.3664 (10)–2.3897 (10) and 2.042 (5)–2.091 (5) Å. The angles at Zn(II) range from 100.99 (15) to 119.06 (4)°, the largest being Br—Zn—Br (Tab. 1). The structural parameters in the dpds molecule are quite regular. In particular the C—S bond, 1.784 (7)–1.783 (6) Å, is in good agreement with those expected for C(sp2)—S bonds (1.77 Å). The S—S bond length, 2.050 (3) Å, is somewhat longer than that found in the structure of the free ligand, 2.016 (2) Å (Raghavan & Seff, 1977).

For related literature, see: Bhosekar et al. (2007); Kinoshita et al. (2003); Kadooka et al. (1976); Kubo et al. (1998); Näther & Jess (2006); Näther et al. (2003); Pickardt et al. (2005); Raghavan & Seff (1977).

Computing details top

Data collection: IPDS Program Package (Stoe, 1998); cell refinement: IPDS Program Package (Stoe, 1998); data reduction: IPDS Program Package (Stoe, 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 SHELXTL (Bruker, 1998).

Figures top
[Figure 1] Fig. 1. : Molecular structure of the title compund with labelling and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. : Crystal structure of the title compound with view along the [0 1 0] direction. Intermolecular C—H···Br hydrogen bonding is shown as dashed lines. Symmetry code: i = x, -1 + y, z.
Dibromido(di-2-pyridyl disulfide-κ2N,N')zinc(II) top
Crystal data top
[ZnBr2(C10H8N2S2)]Z = 2
Mr = 445.49F(000) = 428
Triclinic, P1Dx = 2.177 Mg m−3
a = 7.7610 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.2962 (8) ÅCell parameters from 8000 reflections
c = 12.3576 (13) Åθ = 2.9–28.1°
α = 95.488 (12)°µ = 7.97 mm−1
β = 107.161 (12)°T = 170 K
γ = 112.950 (11)°Block, colourless
V = 679.70 (12) Å30.09 × 0.09 × 0.08 mm
Data collection top
STOE IPDS-1
diffractometer		2167 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Graphite monochromatorθmax = 26.0°, θmin = 2.9°
Phi scansh = −9→9
6076 measured reflectionsk = −10→10
2609 independent reflectionsl = −15→15
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0684P)2 + 2.046P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2609 reflectionsΔρmax = 1.31 e Å−3
155 parametersΔρmin = −1.43 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: 0.0071 (16)
Crystal data top
[ZnBr2(C10H8N2S2)]γ = 112.950 (11)°
Mr = 445.49V = 679.70 (12) Å3
Triclinic, P1Z = 2
a = 7.7610 (8) ÅMo Kα radiation
b = 8.2962 (8) ŵ = 7.97 mm−1
c = 12.3576 (13) ÅT = 170 K
α = 95.488 (12)°0.09 × 0.09 × 0.08 mm
β = 107.161 (12)°
Data collection top
STOE IPDS-1
diffractometer		2167 reflections with I > 2σ(I)
6076 measured reflectionsRint = 0.054
2609 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.06Δρmax = 1.31 e Å−3
2609 reflectionsΔρmin = −1.43 e Å−3
155 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
Br10.99364 (9)0.75728 (8)0.23015 (6)0.0193 (2)
Br20.38203 (9)0.48414 (9)0.12968 (6)0.0197 (2)
Zn10.70460 (10)0.50584 (9)0.22904 (6)0.0143 (2)
S10.7276 (3)0.2365 (2)0.44635 (15)0.0223 (4)
N10.7378 (8)0.5577 (7)0.4048 (5)0.0167 (11)
C20.7679 (9)0.5176 (10)0.5987 (6)0.0222 (14)
H20.76850.44180.65170.027*
C50.7566 (10)0.7263 (9)0.4404 (5)0.0190 (13)
H50.74730.79740.38500.023*
C10.7414 (9)0.4556 (9)0.4828 (5)0.0166 (13)
C30.7933 (10)0.6913 (10)0.6347 (6)0.0248 (15)
H30.81340.73730.71310.030*
C40.7888 (10)0.7975 (10)0.5545 (7)0.0263 (15)
H40.80770.91750.57770.032*
S20.5117 (2)0.1119 (2)0.28313 (15)0.0213 (4)
N110.7411 (7)0.2888 (7)0.1671 (5)0.0151 (10)
C150.8390 (9)0.2991 (9)0.0928 (5)0.0183 (13)
H150.90640.41330.07850.022*
C110.6512 (9)0.1280 (8)0.1897 (5)0.0156 (12)
C140.8465 (10)0.1511 (10)0.0359 (6)0.0237 (15)
H140.91460.1632−0.01750.028*
C130.7523 (10)−0.0148 (9)0.0587 (6)0.0225 (14)
H130.7544−0.11890.02090.027*
C120.6535 (10)−0.0270 (9)0.1385 (6)0.0227 (14)
H120.5899−0.13860.15700.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0160 (3)0.0134 (4)0.0251 (4)0.0025 (3)0.0079 (3)0.0054 (2)
Br20.0136 (3)0.0182 (4)0.0257 (4)0.0065 (3)0.0050 (3)0.0070 (3)
Zn10.0137 (4)0.0105 (4)0.0198 (4)0.0056 (3)0.0067 (3)0.0045 (3)
S10.0257 (9)0.0218 (9)0.0254 (9)0.0145 (7)0.0097 (7)0.0113 (7)
N10.015 (3)0.018 (3)0.019 (3)0.008 (2)0.006 (2)0.006 (2)
C20.016 (3)0.035 (4)0.017 (3)0.013 (3)0.006 (3)0.007 (3)
C50.025 (3)0.018 (3)0.017 (3)0.012 (3)0.008 (3)0.005 (3)
C10.011 (3)0.021 (3)0.021 (3)0.009 (3)0.005 (2)0.007 (3)
C30.022 (3)0.038 (4)0.013 (3)0.013 (3)0.006 (3)0.001 (3)
C40.020 (3)0.021 (4)0.040 (4)0.010 (3)0.013 (3)0.006 (3)
S20.0147 (8)0.0164 (8)0.0303 (9)0.0024 (6)0.0108 (7)0.0054 (7)
N110.012 (2)0.011 (3)0.021 (3)0.005 (2)0.004 (2)0.003 (2)
C150.016 (3)0.020 (3)0.020 (3)0.009 (3)0.008 (3)0.005 (3)
C110.009 (3)0.014 (3)0.021 (3)0.005 (2)0.001 (2)0.006 (2)
C140.020 (3)0.026 (4)0.028 (4)0.014 (3)0.009 (3)0.003 (3)
C130.023 (3)0.023 (4)0.018 (3)0.013 (3)0.003 (3)−0.006 (3)
C120.025 (4)0.015 (3)0.025 (3)0.010 (3)0.004 (3)0.004 (3)
Geometric parameters (Å, º) top
Br1—Zn12.3897 (10)C3—H30.9500
Br2—Zn12.3664 (10)C4—H40.9500
Zn1—N112.042 (5)S2—C111.783 (6)
Zn1—N12.091 (5)N11—C111.343 (8)
S1—C11.784 (7)N11—C151.344 (8)
S1—S22.050 (3)C15—C141.385 (9)
N1—C11.344 (8)C15—H150.9500
N1—C51.362 (8)C11—C121.387 (9)
C2—C31.385 (10)C14—C131.386 (11)
C2—C11.401 (9)C14—H140.9500
C2—H20.9500C13—C121.406 (10)
C5—C41.385 (10)C13—H130.9500
C5—H50.9500C12—H120.9500
C3—C41.389 (11)
N11—Zn1—N1117.2 (2)C5—C4—C3119.2 (6)
N11—Zn1—Br2112.77 (15)C5—C4—H4120.4
N1—Zn1—Br2103.61 (14)C3—C4—H4120.4
N11—Zn1—Br1103.35 (15)C11—S2—S1104.0 (2)
N1—Zn1—Br1100.99 (15)C11—N11—C15118.2 (5)
Br2—Zn1—Br1119.06 (4)C11—N11—Zn1121.2 (4)
C1—S1—S2106.7 (2)C15—N11—Zn1120.3 (4)
C1—N1—C5118.1 (5)N11—C15—C14123.2 (6)
C1—N1—Zn1131.4 (4)N11—C15—H15118.4
C5—N1—Zn1110.4 (4)C14—C15—H15118.4
C3—C2—C1118.8 (6)N11—C11—C12122.8 (6)
C3—C2—H2120.6N11—C11—S2118.3 (4)
C1—C2—H2120.6C12—C11—S2118.8 (5)
N1—C5—C4122.2 (6)C15—C14—C13118.5 (6)
N1—C5—H5118.9C15—C14—H14120.8
C4—C5—H5118.9C13—C14—H14120.8
N1—C1—C2122.5 (6)C14—C13—C12119.1 (6)
N1—C1—S1121.5 (5)C14—C13—H13120.5
C2—C1—S1115.9 (5)C12—C13—H13120.5
C2—C3—C4119.1 (6)C11—C12—C13118.3 (6)
C2—C3—H3120.5C11—C12—H12120.9
C4—C3—H3120.5C13—C12—H12120.9

Experimental details

Crystal data
Chemical formula[ZnBr2(C10H8N2S2)]
Mr445.49
Crystal system, space groupTriclinic, P1
Temperature (K)170
a, b, c (Å)7.7610 (8), 8.2962 (8), 12.3576 (13)
α, β, γ (°)95.488 (12), 107.161 (12), 112.950 (11)
V (Å3)679.70 (12)
Z2
Radiation typeMo Kα
µ (mm−1)7.97
Crystal size (mm)0.09 × 0.09 × 0.08
Data collection
DiffractometerSTOE IPDS1
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		6076, 2609, 2167
Rint0.054
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.120, 1.06
No. of reflections2609
No. of parameters155
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.31, −1.43

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

Selected geometric parameters (Å, º) top
Br1—Zn12.3897 (10)S1—C11.784 (7)
Br2—Zn12.3664 (10)S1—S22.050 (3)
Zn1—N112.042 (5)S2—C111.783 (6)
Zn1—N12.091 (5)
N11—Zn1—N1117.2 (2)N11—Zn1—Br1103.35 (15)
N11—Zn1—Br2112.77 (15)N1—Zn1—Br1100.99 (15)
N1—Zn1—Br2103.61 (14)Br2—Zn1—Br1119.06 (4)
 

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

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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page m83
https://doi.org/10.1107/S1600536807063556
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