(μ-4,4′-Bipyridine-κ2N:N′)bis­[bis­(N,N-dimethyl­dithio­carbamato-κ2S,S′)zinc(II)]

Zha, M.-Q.; Li, X.; Bing, Y.; Lu, Y.

doi:10.1107/S1600536810042650

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1465

https://doi.org/10.1107/S1600536810042650

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(μ-4,4′-Bipyridine-κ²N:N′)bis[bis(N,N-dimethyldithiocarbamato-κ²S,S′)zinc(II)]

Mei-Qin Zha,^a Xing Li,^a ^* Yue Bing ^a and Yue Lu ^a

^aFaculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: lixing@nbu.edu.cn

(Received 29 September 2010; accepted 20 October 2010; online 23 October 2010)

The title dinuclear Zn^II complex, [Zn₂(C₃H₆NS₂)₄(C₁₀H₈N₂)], 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 dimethyldithiocarbamate anions, giving a trigonal-bipyramidal ZnNS₄ geometry. Weak intermolecular 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_r = 767.76
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.101
S = 1.04
3754 reflections
170 parameters
H-atom parameters constrained
Δρ_max = 1.21 e Å⁻³
Δρ_min = −1.95 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042650/xu5042Isup2.hkl

checkCIF report

Comment top

Dialkyldithiocarbamates, (R₂dtc) (where R is an alkyl group such as methyl, ethyl or propyl), have strong metal-binding properties as well as biological functions (Jian et al., 2002; Arora et al., 2003; Hogarth & Richards, 2006). Crystal engineering studies of zinc(II) dithiocarbamates (^-S₂CNR₂) are less well developed (Lai et al., 2002; Chen et al., 2006; Benson et al., 2007), this is likely due to the stronger chelating ability of the dithiocarbamate ligand which tends to preclude incorporation of multiple bridging ligands within the Zn atom coordination sphere. Here, we report the crystal structure of the title zinc complex with 4,4'-bipy and dimethyldithiocarbamate (Me₂dtc), [Zn₂(C₃H₆NS₂)₄(C₁₀H₈N₂)], (I).

Complex (I) is a binuclear structure, in which Zn1A is symmetrical component related by Zn1 (Symmetry code: -x, y + 1/2, -z + 3/2), and the two Zn²⁺ ions possess the same coordination environment (Fig. 1). The Zn²⁺ ion adopts a distorted square-pyramidal coordination geometry comprising two S,S'- bidentate dimethyldithiocarbamate (Me₂dtc) ligands, one N atom from 4,4'-bipy ligand, the N atom in the apical site, Zn—O distances ranging from 2.349 to 2.624 Å and Cd –N distance being 2.064 Å. In the crystal, the molecules are generate to a one-dimensional chain, which is further extended into two-dimensional supramolecular network via weak C—H···S contacts (Fig. 2), and finally assembled into three-dimensional supramolecular network by C—H···π interactions (Fig. 3).

Related literature top

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 top

Tetramethylthiuram monosulfide (5.0 mg, 0.024 mmol) dissolved in N,N-dimethylformamide (DMF) (2 ml) was mixed with a DMF solution (1 ml) of 4,4'-bipy (2.38 mg, 0.012 mmol) and stirred for 20 min at room temperature. A DMF solution (0.2 ml) of Zn(NO₃)₂.6H₂O (3.57 mg, 0.012 mmol) was then added dropwise and the mixture was allowed to react for 15 min. The solution was left at room temperature to allow slow evaporation. After a few days, pale yellow block crystals of (I) were obtained from the mother liquor.

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. The molcular structure of (I) showing displacement ellipsoids at the 30% probability level.
	Fig. 2. Two-dimensional supramolecular framework for (I) by C—H···S interactions (orange dashed lines).
	Fig. 3. Unit-cell contents for (I) viewed in projection down the b axis.

(µ-4,4'-Bipyridine-κ²N:N')bis[bis(N,N- dimethyldithiocarbamato-κ²S,S')zinc(II)] top

Crystal data top

[Zn₂(C₃H₆NS₂)₄(C₁₀H₈N₂)]	F(000) = 788
M_r = 767.76	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0365P)² + 3.8184P] where P = (F_o² + 2F_c²)/3
3754 reflections	(Δ/σ)_max < 0.001
170 parameters	Δρ_max = 1.21 e Å⁻³
0 restraints	Δρ_min = −1.95 e Å⁻³

Crystal data top

[Zn₂(C₃H₆NS₂)₄(C₁₀H₈N₂)]	V = 1629.1 (3) Å³
M_r = 767.76	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0490 (8) Å	µ = 2.01 mm⁻¹
b = 13.8770 (14) Å	T = 173 K
c = 14.8134 (14) Å	0.34 × 0.26 × 0.13 mm
β = 100.070 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3754 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3205 reflections with I > 2σ(I)
T_min = 0.540, T_max = 0.770	R_int = 0.044
14059 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.04	Δρ_max = 1.21 e Å⁻³
3754 reflections	Δρ_min = −1.95 e Å⁻³
170 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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Zn₂(C₃H₆NS₂)₄(C₁₀H₈N₂)]
M_r	767.76
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	8.0490 (8), 13.8770 (14), 14.8134 (14)
β (°)	100.070 (1)
V (Å³)	1629.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.01
Crystal size (mm)	0.34 × 0.26 × 0.13

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.540, 0.770
No. of measured, independent and observed [I > 2σ(I)] reflections	14059, 3754, 3205
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.101, 1.04
No. of reflections	3754
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.21, −1.95

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2.

Acknowledgements

The work was supported by the National Natural Science Foundation of China (20971075), the `Qianjiang Talent' Projects of Zhejiang Province (2009R10032), the Program for Innovative Research Teams of Ningbo Novel Photoelectric Materials and Devices (2009B21007) and the K. C. Wong Magna Fund in Ningbo University.

References

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