Bis(N-butyl-N-ethyl­dithio­carbamato-κ2S,S′)nickel(II)

Wan Juhari, W.N.S.; Baba, I.; Farina, Y.; Ng, S.W.

doi:10.1107/S1600536810006677

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m339

doi:10.1107/S1600536810006677

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Bis(N-butyl-N-ethyldithiocarbamato-κ²S,S′)nickel(II)

Wan Nur Shazwani Wan Juhari,^a Ibrahim Baba,^a Yang Farina ^a and Seik Weng Ng ^b ^*

^aSchool of Chemical Sciences, Universiti Kebangbaan Malaysia, 43600 Bangi, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 21 February 2010; accepted 22 February 2010; online 27 February 2010)

The dithiocarbamate anions in the title compound, [Ni(C₇H₁₄NS₂)₂], chelate to the Ni^II atom, which is four-coordinate in a square-planar geometry. The Ni^II atom lies on a center of inversion.

Related literature

For nickel bis(diethyldithiocarbamate) and nickel bis(dibutyldithiocarbamate), see: Bonamico et al. (1965 ); Khan et al. (1987 ); Lokaj et al. (1984 ).

Experimental

Crystal data

[Ni(C₇H₁₄NS₂)₂]
M_r = 411.33
Monoclinic, P 2₁ /n
a = 8.5641 (9) Å
b = 8.6316 (9) Å
c = 13.6047 (14) Å
β = 94.753 (2)°
V = 1002.23 (18) Å³
Z = 2
Mo Kα radiation
μ = 1.38 mm⁻¹
T = 293 K
0.25 × 0.25 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.724, T_max = 0.934
9338 measured reflections
2295 independent reflections
1628 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.098
S = 1.03
2295 reflections
99 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006677/sj2734sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006677/sj2734Isup2.hkl

checkCIF report

Related literature top

For nickel bis(diethyldithiocarbamate) and nickel bis(dibutyldithiocarbamate), see: Bonamico et al. (1965); Khan et al. (1987); Lokaj et al. (1984).

Experimental top

Nickel(II) chloride (10 mmol), butylethylamine (10 mmol) and carbon disulfide (10 mmol) were reacted in ethanol (50 ml) at 277 K to produce a brown solid. The mixture was stirred for an hour. The solid was collected and recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Ni(C₇H₁₄NS₂)₂ at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Bis(N-butyl-N-ethyldithiocarbamato- κ²S,S')nickel(II) top

Crystal data top

[Ni(C₇H₁₄NS₂)₂]	F(000) = 436
M_r = 411.33	D_x = 1.363 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2307 reflections
a = 8.5641 (9) Å	θ = 2.4–24.6°
b = 8.6316 (9) Å	µ = 1.38 mm⁻¹
c = 13.6047 (14) Å	T = 293 K
β = 94.753 (2)°	Plate, brown
V = 1002.23 (18) Å³	0.25 × 0.25 × 0.05 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	2295 independent reflections
Radiation source: fine-focus sealed tube	1628 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 27.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
T_min = 0.724, T_max = 0.934	k = −11→11
9338 measured reflections	l = −17→15

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0469P)² + 0.1755P] where P = (F_o² + 2F_c²)/3
2295 reflections	(Δ/σ)_max = 0.001
99 parameters	Δρ_max = 0.38 e Å⁻³
6 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

[Ni(C₇H₁₄NS₂)₂]	V = 1002.23 (18) Å³
M_r = 411.33	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.5641 (9) Å	µ = 1.38 mm⁻¹
b = 8.6316 (9) Å	T = 293 K
c = 13.6047 (14) Å	0.25 × 0.25 × 0.05 mm
β = 94.753 (2)°

Data collection top

Bruker SMART APEX diffractometer	2295 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1628 reflections with I > 2σ(I)
T_min = 0.724, T_max = 0.934	R_int = 0.029
9338 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	6 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	Δρ_max = 0.38 e Å⁻³
2295 reflections	Δρ_min = −0.21 e Å⁻³
99 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.5000	0.5000	0.05331 (16)
S1	0.75597 (8)	0.48176 (8)	0.53089 (5)	0.0629 (2)
S2	0.52687 (8)	0.56847 (9)	0.65651 (5)	0.0631 (2)
N1	0.8339 (3)	0.5601 (3)	0.72015 (17)	0.0647 (6)
C1	0.7236 (3)	0.5403 (3)	0.64766 (19)	0.0564 (6)
C2	0.7964 (3)	0.6124 (3)	0.81795 (18)	0.0658 (7)
H2A	0.7008	0.6732	0.8111	0.079*
H2B	0.8799	0.6791	0.8456	0.079*
C3	0.7752 (4)	0.4796 (3)	0.8887 (2)	0.0746 (8)
H3A	0.6875	0.4163	0.8630	0.090*
H3B	0.8684	0.4154	0.8928	0.090*
C4	0.7460 (4)	0.5353 (4)	0.9904 (2)	0.0836 (9)
H4A	0.6554	0.6032	0.9856	0.100*
H4B	0.8355	0.5955	1.0167	0.100*
C5	0.7180 (4)	0.4044 (4)	1.0615 (2)	0.1014 (11)
H5A	0.6962	0.4470	1.1241	0.152*
H5B	0.8098	0.3403	1.0699	0.152*
H5C	0.6305	0.3433	1.0356	0.152*
C6	1.0008 (4)	0.5276 (4)	0.7074 (2)	0.0805 (9)
H6A	1.0079	0.4559	0.6530	0.097*
H6B	1.0490	0.4791	0.7667	0.097*
C7	1.0871 (4)	0.6734 (4)	0.6871 (2)	0.0951 (10)
H7A	1.1957	0.6500	0.6818	0.143*
H7B	1.0780	0.7453	0.7401	0.143*
H7C	1.0432	0.7183	0.6265	0.143*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0586 (3)	0.0553 (3)	0.0464 (3)	−0.0031 (2)	0.0063 (2)	−0.00089 (19)
S1	0.0628 (4)	0.0763 (4)	0.0504 (4)	0.0013 (3)	0.0095 (3)	−0.0089 (3)
S2	0.0589 (4)	0.0785 (5)	0.0526 (4)	0.0006 (3)	0.0090 (3)	−0.0081 (3)
N1	0.0596 (13)	0.0780 (14)	0.0572 (13)	0.0057 (11)	0.0077 (11)	−0.0171 (12)
C1	0.0629 (16)	0.0556 (14)	0.0513 (15)	−0.0005 (11)	0.0083 (12)	−0.0052 (11)
C2	0.0670 (17)	0.0758 (17)	0.0542 (16)	0.0016 (13)	0.0023 (13)	−0.0198 (13)
C3	0.080 (2)	0.080 (2)	0.0629 (18)	0.0053 (14)	0.0010 (15)	−0.0130 (15)
C4	0.093 (2)	0.096 (2)	0.0621 (19)	0.0055 (17)	0.0047 (17)	−0.0136 (17)
C5	0.118 (3)	0.111 (3)	0.074 (2)	0.001 (2)	0.002 (2)	0.000 (2)
C6	0.0653 (18)	0.109 (3)	0.0660 (19)	0.0082 (17)	−0.0034 (15)	−0.0236 (17)
C7	0.076 (2)	0.125 (3)	0.086 (2)	0.008 (2)	0.0171 (17)	−0.006 (2)

Geometric parameters (Å, º) top

Ni1—S1ⁱ	2.2032 (8)	C3—H3B	0.9700
Ni1—S1	2.2032 (8)	C4—C5	1.519 (4)
Ni1—S2	2.2034 (7)	C4—H4A	0.9700
Ni1—S2ⁱ	2.2034 (7)	C4—H4B	0.9700
S1—C1	1.712 (3)	C5—H5A	0.9600
S2—C1	1.716 (3)	C5—H5B	0.9600
N1—C1	1.319 (3)	C5—H5C	0.9600
N1—C2	1.466 (3)	C6—C7	1.497 (4)
N1—C6	1.481 (4)	C6—H6A	0.9700
C2—C3	1.517 (4)	C6—H6B	0.9700
C2—H2A	0.9700	C7—H7A	0.9600
C2—H2B	0.9700	C7—H7B	0.9600
C3—C4	1.505 (4)	C7—H7C	0.9600
C3—H3A	0.9700

S1ⁱ—Ni1—S1	180.0	H3A—C3—H3B	107.9
S1ⁱ—Ni1—S2	100.82 (2)	C3—C4—C5	113.3 (3)
S1—Ni1—S2	79.18 (2)	C3—C4—H4A	108.9
S1ⁱ—Ni1—S2ⁱ	79.18 (2)	C5—C4—H4A	108.9
S1—Ni1—S2ⁱ	100.82 (2)	C3—C4—H4B	108.9
S2—Ni1—S2ⁱ	180.0	C5—C4—H4B	108.9
C1—S1—Ni1	85.45 (10)	H4A—C4—H4B	107.7
C1—S2—Ni1	85.34 (9)	C4—C5—H5A	109.5
C1—N1—C2	121.4 (2)	C4—C5—H5B	109.5
C1—N1—C6	121.7 (2)	H5A—C5—H5B	109.5
C2—N1—C6	116.8 (2)	C4—C5—H5C	109.5
N1—C1—S1	124.8 (2)	H5A—C5—H5C	109.5
N1—C1—S2	125.1 (2)	H5B—C5—H5C	109.5
S1—C1—S2	110.04 (16)	N1—C6—C7	111.0 (3)
N1—C2—C3	113.0 (2)	N1—C6—H6A	109.4
N1—C2—H2A	109.0	C7—C6—H6A	109.4
C3—C2—H2A	109.0	N1—C6—H6B	109.4
N1—C2—H2B	109.0	C7—C6—H6B	109.4
C3—C2—H2B	109.0	H6A—C6—H6B	108.0
H2A—C2—H2B	107.8	C6—C7—H7A	109.5
C4—C3—C2	112.3 (2)	C6—C7—H7B	109.5
C4—C3—H3A	109.1	H7A—C7—H7B	109.5
C2—C3—H3A	109.1	C6—C7—H7C	109.5
C4—C3—H3B	109.1	H7A—C7—H7C	109.5
C2—C3—H3B	109.1	H7B—C7—H7C	109.5

S2—Ni1—S1—C1	−0.24 (9)	Ni1—S1—C1—S2	0.32 (12)
S2ⁱ—Ni1—S1—C1	179.76 (9)	Ni1—S2—C1—N1	180.0 (2)
S1ⁱ—Ni1—S2—C1	−179.76 (9)	Ni1—S2—C1—S1	−0.32 (12)
S1—Ni1—S2—C1	0.24 (9)	C1—N1—C2—C3	94.2 (3)
C2—N1—C1—S1	179.3 (2)	C6—N1—C2—C3	−84.6 (3)
C6—N1—C1—S1	−2.0 (4)	N1—C2—C3—C4	176.7 (3)
C2—N1—C1—S2	−1.0 (4)	C2—C3—C4—C5	177.8 (3)
C6—N1—C1—S2	177.6 (2)	C1—N1—C6—C7	98.5 (3)
Ni1—S1—C1—N1	−180.0 (2)	C2—N1—C6—C7	−82.8 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₇H₁₄NS₂)₂]
M_r	411.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.5641 (9), 8.6316 (9), 13.6047 (14)
β (°)	94.753 (2)
V (Å³)	1002.23 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.38
Crystal size (mm)	0.25 × 0.25 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.724, 0.934
No. of measured, independent and observed [I > 2σ(I)] reflections	9338, 2295, 1628
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.098, 1.03
No. of reflections	2295
No. of parameters	99
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.21

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank Universiti Kebangsaan Malaysia (UKM-GUP-NBT-08-27-111 and 06-01-02-SF0539) and the University of Malaya for supporting this study.

References

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