(μ-4,4'-Bipyridine-κN:N')bis-[bis-(N,N-dimethyl-dithio-carbamato-κS,S')zinc(II)].

The title dinuclear Zn(II) complex, [Zn(2)(C(3)H(6)NS(2))(4)(C(10)H(8)N(2))], is centrosymmetric; the mid-point of the C-C bond linking the two pyridine rings is located on an inversion center. The pyridine N atom coordinates to the Zn(II) cation, which is also chelated by two dimethyl-dithio-carbamate anions, giving a trigonal-bipyramidal ZnNS(4) geometry. Weak inter-molecular C-H⋯S hydrogen bonding is present in the crystal structure.

Related literature

Dialkyl­dithio­carbamates have strong metal-binding properties as well as biological functions, see: Jian et al. (2002 ▶); Arora et al. (2003 ▶); Hogarth & Richards (2006 ▶). For related zinc(II) dithio­carbamate compounds, see: Lai et al. (2002 ▶); Chen et al. (2006 ▶); Benson et al. (2007 ▶).

Experimental

Crystal data

[Zn2(C3H6NS2)4(C10H8N2)]

M = 767.76

Monoclinic,

a = 8.0490 (8) Å

b = 13.8770 (14) Å

c = 14.8134 (14) Å

β = 100.070 (1)°

V = 1629.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.01 mm−1

T = 173 K

0.34 × 0.26 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.540, T max = 0.770

14059 measured reflections

3754 independent reflections

3205 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.101

S = 1.04

3754 reflections

170 parameters

H-atom parameters constrained

Δρmax = 1.21 e Å−3

Δρmin = −1.95 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042650/xu5042sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042650/xu5042Isup2.hkl

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

[Zn2(C3H6NS2)4(C10H8N2)]	F(000) = 788
Mr = 767.76	Dx = 1.565 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14059 reflections
a = 8.0490 (8) Å	θ = 2.0–27.5°
b = 13.8770 (14) Å	µ = 2.01 mm−1
c = 14.8134 (14) Å	T = 173 K
β = 100.070 (1)°	Block, yellow
V = 1629.1 (3) Å3	0.34 × 0.26 × 0.13 mm
Z = 2

Bruker SMART 1000 CCD area-detector diffractometer	3754 independent reflections
Radiation source: fine-focus sealed tube	3205 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.540, Tmax = 0.770	k = −18→15
14059 measured reflections	l = −18→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0365P)2 + 3.8184P] where P = (Fo2 + 2Fc2)/3
3754 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 1.21 e Å−3
0 restraints	Δρmin = −1.95 e Å−3

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.

	x	y	z	Uiso*/Ueq
Zn1	0.13314 (4)	0.27435 (3)	0.24330 (2)	0.02256 (11)
S1	0.08181 (9)	0.16003 (5)	0.10290 (5)	0.02256 (11)
S2	−0.12799 (10)	0.31820 (6)	0.15575 (6)	0.02636 (18)
S3	0.39861 (9)	0.33093 (6)	0.22187 (5)	0.02260 (17)
S4	0.21808 (10)	0.41611 (6)	0.35942 (6)	0.02694 (18)
C1	−0.0291 (4)	0.1060 (2)	0.3154 (2)	0.0286 (7)
H1A	−0.0887	0.1049	0.2541	0.034*
C2	−0.0689 (4)	0.0385 (2)	0.3764 (2)	0.0292 (7)
H2A	−0.1562	−0.0069	0.3570	0.035*
C3	0.0183 (4)	0.0363 (2)	0.46632 (19)	0.0183 (6)
C4	0.1429 (4)	0.1065 (2)	0.4901 (2)	0.0236 (6)
H4A	0.2065	0.1084	0.5504	0.028*
C5	0.1731 (4)	0.1731 (2)	0.4255 (2)	0.0235 (6)
H5A	0.2568	0.2209	0.4434	0.028*
C6	−0.1905 (5)	0.1389 (3)	−0.0636 (3)	0.0444 (10)
H6A	−0.0751	0.1136	−0.0503	0.067*
H6B	−0.2123	0.1658	−0.1257	0.067*
H6C	−0.2706	0.0867	−0.0591	0.067*
C7	−0.3640 (5)	0.2736 (4)	−0.0185 (3)	0.0495 (11)
H7A	−0.4042	0.2895	0.0385	0.074*
H7B	−0.4514	0.2375	−0.0591	0.074*
H7C	−0.3387	0.3332	−0.0489	0.074*
C8	−0.0971 (4)	0.2285 (2)	0.0785 (2)	0.0230 (6)
C9	0.6095 (5)	0.5119 (3)	0.2449 (3)	0.0372 (8)
H9A	0.5971	0.4609	0.1985	0.056*
H9B	0.7211	0.5072	0.2836	0.056*
H9C	0.5976	0.5750	0.2147	0.056*
C10	0.4667 (5)	0.5812 (3)	0.3652 (3)	0.0362 (8)
H10A	0.3668	0.5723	0.3939	0.054*
H10B	0.4570	0.6421	0.3312	0.054*
H10C	0.5680	0.5825	0.4127	0.054*
C11	0.3763 (4)	0.4248 (2)	0.2965 (2)	0.0206 (6)
N1	0.0906 (3)	0.17348 (17)	0.33906 (17)	0.0203 (5)
N2	−0.2105 (3)	0.2147 (2)	0.0027 (2)	0.0331 (7)
N3	0.4789 (3)	0.50091 (19)	0.30182 (18)	0.0255 (6)

	U11	U22	U33	U12	U13	U23
Zn1	0.02293 (17)	0.02255 (18)	0.02164 (18)	−0.00291 (12)	0.00229 (12)	0.00392 (12)
S1	0.02293 (17)	0.02255 (18)	0.02164 (18)	−0.00291 (12)	0.00229 (12)	0.00392 (12)
S2	0.0227 (4)	0.0276 (4)	0.0287 (4)	0.0040 (3)	0.0042 (3)	0.0005 (3)
S3	0.0212 (3)	0.0237 (4)	0.0230 (4)	−0.0016 (3)	0.0042 (3)	−0.0034 (3)
S4	0.0300 (4)	0.0249 (4)	0.0284 (4)	−0.0040 (3)	0.0119 (3)	−0.0024 (3)
C1	0.0389 (18)	0.0250 (16)	0.0183 (15)	−0.0113 (13)	−0.0045 (13)	0.0017 (12)
C2	0.0391 (18)	0.0238 (16)	0.0216 (15)	−0.0152 (14)	−0.0032 (13)	0.0036 (12)
C3	0.0251 (14)	0.0133 (13)	0.0171 (13)	−0.0003 (11)	0.0055 (11)	−0.0020 (11)
C4	0.0269 (15)	0.0259 (16)	0.0167 (14)	−0.0071 (12)	0.0002 (11)	0.0008 (12)
C5	0.0240 (14)	0.0245 (16)	0.0217 (15)	−0.0074 (12)	0.0032 (12)	−0.0016 (12)
C6	0.039 (2)	0.065 (3)	0.0268 (18)	−0.0130 (19)	0.0011 (15)	−0.0150 (18)
C7	0.0289 (19)	0.072 (3)	0.043 (2)	0.0039 (19)	−0.0056 (17)	0.006 (2)
C8	0.0222 (14)	0.0263 (16)	0.0213 (15)	−0.0054 (12)	0.0057 (11)	0.0024 (12)
C9	0.0364 (18)	0.036 (2)	0.043 (2)	−0.0150 (15)	0.0175 (16)	−0.0078 (16)
C10	0.042 (2)	0.0242 (17)	0.045 (2)	−0.0088 (15)	0.0146 (16)	−0.0106 (15)
C11	0.0202 (13)	0.0212 (14)	0.0190 (14)	0.0016 (11)	−0.0004 (11)	0.0035 (11)
N1	0.0254 (12)	0.0168 (12)	0.0186 (12)	−0.0027 (10)	0.0034 (10)	0.0014 (9)
N2	0.0236 (13)	0.0464 (18)	0.0279 (15)	−0.0042 (12)	0.0005 (11)	0.0005 (13)
N3	0.0268 (13)	0.0219 (13)	0.0290 (14)	−0.0045 (10)	0.0082 (11)	−0.0022 (11)

Zn1—N1	2.064 (2)	C5—H5A	0.9500
Zn1—S1	2.5909 (9)	C6—N2	1.467 (5)
Zn1—S2	2.3488 (9)	C6—H6A	0.9800
Zn1—S3	2.3495 (8)	C6—H6B	0.9800
Zn1—S4	2.6239 (9)	C6—H6C	0.9800
S1—C8	1.710 (3)	C7—N2	1.468 (5)
S2—C8	1.738 (3)	C7—H7A	0.9800
S3—C11	1.738 (3)	C7—H7B	0.9800
S4—C11	1.708 (3)	C7—H7C	0.9800
C1—N1	1.345 (4)	C8—N2	1.331 (4)
C1—C2	1.378 (4)	C9—N3	1.466 (4)
C1—H1A	0.9500	C9—H9A	0.9800
C2—C3	1.393 (4)	C9—H9B	0.9800
C2—H2A	0.9500	C9—H9C	0.9800
C3—C4	1.398 (4)	C10—N3	1.471 (4)
C3—C3i	1.483 (6)	C10—H10A	0.9800
C4—C5	1.383 (4)	C10—H10B	0.9800
C4—H4A	0.9500	C10—H10C	0.9800
C5—N1	1.335 (4)	C11—N3	1.334 (4)
N1—Zn1—S2	108.37 (7)	H6B—C6—H6C	109.5
N1—Zn1—S3	125.72 (7)	N2—C7—H7A	109.5
S2—Zn1—S3	125.87 (3)	N2—C7—H7B	109.5
N1—Zn1—S1	96.55 (7)	H7A—C7—H7B	109.5
S2—Zn1—S1	73.36 (3)	N2—C7—H7C	109.5
S3—Zn1—S1	96.74 (3)	H7A—C7—H7C	109.5
N1—Zn1—S4	96.52 (7)	H7B—C7—H7C	109.5
S2—Zn1—S4	105.85 (3)	N2—C8—S1	121.7 (3)
S3—Zn1—S4	72.49 (3)	N2—C8—S2	120.2 (3)
S1—Zn1—S4	166.41 (3)	S1—C8—S2	118.10 (18)
C8—S1—Zn1	80.77 (11)	N3—C9—H9A	109.5
C8—S2—Zn1	87.75 (11)	N3—C9—H9B	109.5
C11—S3—Zn1	88.10 (10)	H9A—C9—H9B	109.5
C11—S4—Zn1	80.15 (10)	N3—C9—H9C	109.5
N1—C1—C2	122.7 (3)	H9A—C9—H9C	109.5
N1—C1—H1A	118.6	H9B—C9—H9C	109.5
C2—C1—H1A	118.6	N3—C10—H10A	109.5
C1—C2—C3	120.4 (3)	N3—C10—H10B	109.5
C1—C2—H2A	119.8	H10A—C10—H10B	109.5
C3—C2—H2A	119.8	N3—C10—H10C	109.5
C2—C3—C4	116.4 (3)	H10A—C10—H10C	109.5
C2—C3—C3i	122.1 (3)	H10B—C10—H10C	109.5
C4—C3—C3i	121.5 (3)	N3—C11—S4	122.4 (2)
C5—C4—C3	119.8 (3)	N3—C11—S3	119.9 (2)
C5—C4—H4A	120.1	S4—C11—S3	117.64 (17)
C3—C4—H4A	120.1	C5—N1—C1	117.4 (3)
N1—C5—C4	123.2 (3)	C5—N1—Zn1	123.2 (2)
N1—C5—H5A	118.4	C1—N1—Zn1	119.4 (2)
C4—C5—H5A	118.4	C8—N2—C6	121.9 (3)
N2—C6—H6A	109.5	C8—N2—C7	121.8 (3)
N2—C6—H6B	109.5	C6—N2—C7	116.3 (3)
H6A—C6—H6B	109.5	C11—N3—C9	123.2 (3)
N2—C6—H6C	109.5	C11—N3—C10	121.8 (3)
H6A—C6—H6C	109.5	C9—N3—C10	115.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···S3ii	0.95	2.86	3.782 (3)	164

Table 1

Selected bond lengths (Å)

Zn1—N1	2.064 (2)
Zn1—S1	2.5909 (9)
Zn1—S2	2.3488 (9)
Zn1—S3	2.3495 (8)
Zn1—S4	2.6239 (9)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯S3i	0.95	2.86	3.782 (3)	164

Symmetry code: (i) .