Bis{2-[2-(isopropyl­ammonio)ethyl­imino­meth­yl]-6-methoxy­phenolato}nickel(II) dithio­cyanate

Ma, H.-B.; Jiang, Y.-X.; Lei, J.-T.

doi:10.1107/S1600536808008052

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages m597-m598

doi:10.1107/S1600536808008052

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Bis{2-[2-(isopropylammonio)ethyliminomethyl]-6-methoxyphenolato}nickel(II) dithiocyanate

Hong-Bo Ma,^a Yan-Xia Jiang ^b and Jun-Tao Lei ^c ^*

^aDepartment of Nutrition, Jilin Medical College, Jilin 132013, People's Republic of China, ^bDepartment of Biochemistry, Jilin Medical College, Jilin 132013, People's Republic of China, and ^cDepartment of Pharmacopedics, Jilin Medical College, Jilin 132013, People's Republic of China
^*Correspondence e-mail: jlcpcxb@yahoo.com.cn

(Received 20 March 2008; accepted 25 March 2008; online 29 March 2008)

The title complex, [Ni(C₁₃H₂₀N₂O₂)₂](NCS)₂, consists of a centrosymmetric mononuclear four-coordinate nickel(II) complex cation and two thiocyanate anions. The Ni atom is located on an inversion center and is coordinated by two phenol O atoms and two imine N atoms from two equivalent Schiff base ligands, in a square-planar geometry. In the crystal structure, the amino H atoms are involved in N—H⋯O hydrogen bonds with the phenol and methoxy O atoms of the ligand, and in N—H⋯N hydrogen bonds with the N atoms of the thiocyanate anions, which sit above and below the Ni atom.

Related literature

For background on the chemistry of Schiff base nickel(II) complexes, see: Marganian et al. (1995 ). For their biological activity, see: Harrop et al. (2003 ); Brückner et al. (2000 ); Ren et al. (2002 ). For thiocyanate-coordinated complexes, see: Bogdanović et al. (2005 ); Schottenfeld et al. (2007 ); Abul-Haj et al. (2000 ). For related structures, see: Arıcı et al. (2005 ); Diao (2007 ); Diao et al. (2007 ); Zhu et al. (2004 ); Van Hecke et al. (2007 ); de Castro et al. (2001 ).

Experimental

Crystal data

[Ni(C₁₃H₂₀N₂O₂)₂](NCS)₂
M_r = 647.49
Orthorhombic, P b c a
a = 13.520 (2) Å
b = 9.810 (3) Å
c = 24.102 (3) Å
V = 3196.7 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.78 mm⁻¹
T = 298 (2) K
0.23 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.841, T_max = 0.860
24542 measured reflections
3863 independent reflections
1895 reflections with I > 2σ(I)
R_int = 0.110

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.175
S = 1.01
3863 reflections
190 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2ⁱ	0.90	2.34	3.068 (5)	138
N2—H2B⋯O1ⁱ	0.90	1.88	2.664 (4)	145
N2—H2A⋯N3	0.90	2.13	2.983 (6)	158
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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 global, I. DOI: 10.1107/S1600536808008052/su2049sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008052/su2049Isup2.hkl

checkCIF report

Comment top

Nickel(II) complexes derived from Schiff bases have been widely studied (Marganian et al., 1995). Some of them have been found to have pharmacological and antitumor properties (Harrop et al., 2003; Brückner et al., 2000; Ren et al., 2002). The thiocyanate ligand displays a number of coordination modes and has become one of the most extensively studied building blocks in the synthesis of complexes (Bogdanović et al., 2005; Schottenfeld et al., 2007; Abul-Haj et al., 2000), however, the thiocyanate group acting as a counterion in complexes has seldom been reported. We report herein the crystal structure of the title nickel(II) complex (I).

Complex (I) consists of a centrosymmetric mononuclear four-coordinated nickel(II) complex molecule and two thiocyanate anions (Fig. 1). The Ni atom is located on an inversion center and coordinated, by two phenolic O atoms and two imine N atoms from two equivalent Schiff base ligands, in a square planar geometry. The thiocyanate anions act as counterions and are not coordinate to the nickel(II) atom (Fig. 1). All the coordinate bond values are similar to those observed in other Schiff base nickel(II) complexes (Arıcı et al., 2005; Diao, 2007; Diao et al., 2007; Zhu et al., 2004; Van Hecke et al., 2007; de Castro et al., 2001).

In the crystal structure of (I) the amino H-atoms are involved in N-H···O hydrogen bonds with the phenolic and methoxy O atoms of the ligand, and in N-H···N hydrogen bonds with the N-atom of the thiocyanate anions, which sit above and below the nickel atom (Table 1).

Related literature top

For background on the chemistry of Schiff base nickel(II) complexes, see: Marganian et al. (1995). For their biological activity, see: Harrop et al. (2003); Brückner et al. (2000); Ren et al. (2002). For thiocyanate coordinated complexes, see: Bogdanović et al. (2005); Schottenfeld et al. (2007); Abul-Haj et al. (2000). For related structures, see: Arıcı et al. (2005); Diao (2007); Diao et al. (2007); Zhu et al. (2004); Van Hecke et al. (2007); de Castro et al. (2001).

Experimental top

3-Methoxysalicylaldehyde (1.0 mmol, 152.0 mg), N-isopropylethane-1,2-diamine (1.0 mmol, 122.2 mg), ammonium thiocyanate (1.0 mmol, 76.0 mg), and Ni(NO₃)₂.6H₂O (0.5 mmol, 145.0 mg) were dissolved in methanol (50 ml). The mixture was stirred at reflux for 2h to give a reddish solution. After keeping the solution in air for a few days, red block-like crystals were formed.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 molecular structure of complex (I), with displacement ellipsoids drawn at the 30% probability level.

Bis{2-[2-(isopropylammonio)ethyliminomethyl]-6-methoxyphenolato}nickel(II) dithiocyanate top

Crystal data top

[Ni(C₁₃H₂₀N₂O₂)₂](NCS)₂	D_x = 1.345 Mg m⁻³
M_r = 647.49	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1440 reflections
a = 13.520 (2) Å	θ = 2.3–24.6°
b = 9.810 (3) Å	µ = 0.78 mm⁻¹
c = 24.102 (3) Å	T = 298 K
V = 3196.7 (12) Å³	Block, red
Z = 4	0.23 × 0.22 × 0.20 mm
F(000) = 1368

Data collection top

Bruker SMART CCD area-detector diffractometer	3863 independent reflections
Radiation source: fine-focus sealed tube	1895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.110
ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→17
T_min = 0.841, T_max = 0.860	k = −12→12
24542 measured reflections	l = −31→31

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0594P)² + 2.0547P] where P = (F_o² + 2F_c²)/3
3863 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.29 e Å⁻³
6 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Ni(C₁₃H₂₀N₂O₂)₂](NCS)₂	V = 3196.7 (12) Å³
M_r = 647.49	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 13.520 (2) Å	µ = 0.78 mm⁻¹
b = 9.810 (3) Å	T = 298 K
c = 24.102 (3) Å	0.23 × 0.22 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3863 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1895 reflections with I > 2σ(I)
T_min = 0.841, T_max = 0.860	R_int = 0.110
24542 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	6 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.01	Δρ_max = 0.29 e Å⁻³
3863 reflections	Δρ_min = −0.38 e Å⁻³
190 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
Ni1	0.0000	0.5000	0.5000	0.0503 (3)
O1	0.0862 (2)	0.5589 (3)	0.55717 (11)	0.0595 (8)
O2	0.1713 (2)	0.7110 (3)	0.62919 (13)	0.0679 (9)
S1	0.12952 (16)	0.8799 (3)	0.34887 (10)	0.1446 (9)
N1	0.1017 (2)	0.3634 (3)	0.47434 (13)	0.0462 (8)
N2	0.0395 (3)	0.4013 (3)	0.35925 (13)	0.0511 (9)
H2A	0.0740	0.4743	0.3710	0.061*
H2B	−0.0197	0.4034	0.3763	0.061*
N3	0.1018 (5)	0.6596 (5)	0.4145 (3)	0.123 (2)
C1	0.1838 (3)	0.5537 (4)	0.55731 (16)	0.0479 (10)
C2	0.2397 (3)	0.4670 (4)	0.52411 (17)	0.0474 (10)
C3	0.3429 (3)	0.4673 (5)	0.5277 (2)	0.0566 (12)
H3	0.3799	0.4086	0.5056	0.068*
C4	0.3893 (3)	0.5529 (5)	0.5634 (2)	0.0659 (13)
H4	0.4581	0.5543	0.5648	0.079*
C5	0.3353 (3)	0.6389 (5)	0.59804 (19)	0.0610 (13)
H5	0.3678	0.6967	0.6226	0.073*
C6	0.2337 (3)	0.6377 (4)	0.59571 (17)	0.0523 (11)
C7	0.2135 (4)	0.8054 (5)	0.6670 (2)	0.0850 (16)
H7A	0.2530	0.7573	0.6937	0.127*
H7B	0.1617	0.8540	0.6857	0.127*
H7C	0.2544	0.8687	0.6471	0.127*
C8	0.1937 (3)	0.3693 (4)	0.48742 (15)	0.0493 (11)
H8	0.2349	0.3040	0.4717	0.059*
C9	0.0744 (3)	0.2481 (4)	0.43785 (17)	0.0553 (11)
H9A	0.0050	0.2267	0.4433	0.066*
H9B	0.1126	0.1686	0.4484	0.066*
C10	0.0920 (3)	0.2777 (4)	0.37715 (17)	0.0560 (11)
H10A	0.1623	0.2892	0.3707	0.067*
H10B	0.0697	0.2009	0.3551	0.067*
C11	0.0231 (4)	0.4150 (5)	0.29841 (17)	0.0681 (14)
H11	−0.0102	0.3323	0.2853	0.082*
C12	0.1198 (4)	0.4270 (7)	0.2686 (2)	0.119 (2)
H12A	0.1559	0.5037	0.2829	0.178*
H12B	0.1080	0.4397	0.2297	0.178*
H12C	0.1577	0.3453	0.2741	0.178*
C13	−0.0449 (5)	0.5349 (6)	0.2881 (2)	0.0964 (19)
H13A	−0.1083	0.5172	0.3045	0.145*
H13B	−0.0526	0.5481	0.2489	0.145*
H13C	−0.0169	0.6155	0.3043	0.145*
C14	0.1096 (5)	0.7465 (7)	0.3872 (3)	0.095 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0405 (4)	0.0602 (5)	0.0501 (4)	0.0056 (4)	−0.0042 (4)	−0.0156 (4)
O1	0.0406 (17)	0.084 (2)	0.0535 (18)	0.0023 (15)	0.0001 (14)	−0.0189 (16)
O2	0.066 (2)	0.069 (2)	0.068 (2)	−0.0026 (17)	−0.0098 (17)	−0.0192 (18)
S1	0.1218 (16)	0.166 (2)	0.1462 (18)	0.0331 (15)	0.0288 (14)	0.0599 (16)
N1	0.049 (2)	0.049 (2)	0.0408 (19)	−0.0021 (17)	0.0034 (16)	0.0038 (16)
N2	0.057 (2)	0.052 (2)	0.045 (2)	0.0072 (18)	0.0093 (17)	−0.0007 (17)
N3	0.162 (5)	0.062 (3)	0.147 (5)	0.011 (3)	−0.065 (4)	0.008 (3)
C1	0.046 (3)	0.053 (2)	0.045 (2)	−0.002 (2)	−0.004 (2)	0.008 (2)
C2	0.049 (3)	0.050 (3)	0.043 (2)	0.004 (2)	0.001 (2)	0.0088 (19)
C3	0.042 (3)	0.067 (3)	0.060 (3)	0.004 (2)	0.002 (2)	0.007 (2)
C4	0.045 (3)	0.082 (3)	0.071 (3)	−0.003 (3)	−0.006 (2)	0.014 (3)
C5	0.061 (3)	0.063 (3)	0.059 (3)	−0.015 (2)	−0.016 (2)	0.017 (2)
C6	0.052 (3)	0.052 (3)	0.053 (3)	−0.003 (2)	−0.005 (2)	0.008 (2)
C7	0.107 (4)	0.069 (3)	0.079 (4)	−0.008 (3)	−0.023 (3)	−0.013 (3)
C8	0.054 (3)	0.056 (3)	0.038 (2)	0.011 (2)	0.0101 (19)	0.0086 (19)
C9	0.071 (3)	0.045 (2)	0.051 (3)	0.004 (2)	0.003 (2)	−0.001 (2)
C10	0.070 (3)	0.048 (3)	0.050 (3)	0.012 (2)	0.000 (2)	−0.004 (2)
C11	0.095 (4)	0.065 (3)	0.044 (3)	0.010 (3)	−0.001 (3)	−0.001 (2)
C12	0.141 (6)	0.157 (6)	0.058 (4)	0.035 (5)	0.041 (4)	0.028 (4)
C13	0.137 (5)	0.080 (4)	0.072 (4)	0.032 (4)	−0.025 (4)	0.007 (3)
C14	0.095 (4)	0.075 (4)	0.116 (5)	0.015 (4)	−0.039 (4)	−0.022 (4)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.895 (3)	C4—H4	0.9300
Ni1—O1	1.895 (3)	C5—C6	1.374 (6)
Ni1—N1ⁱ	2.017 (3)	C5—H5	0.9300
Ni1—N1	2.017 (3)	C7—H7A	0.9600
O1—C1	1.320 (5)	C7—H7B	0.9600
O2—C6	1.371 (5)	C7—H7C	0.9600
O2—C7	1.418 (5)	C8—H8	0.9300
S1—C14	1.624 (8)	C9—C10	1.511 (5)
N1—C8	1.285 (5)	C9—H9A	0.9700
N1—C9	1.479 (5)	C9—H9B	0.9700
N2—C10	1.470 (5)	C10—H10A	0.9700
N2—C11	1.489 (5)	C10—H10B	0.9700
N2—H2A	0.9000	C11—C12	1.497 (7)
N2—H2B	0.9000	C11—C13	1.513 (7)
N3—C14	1.082 (7)	C11—H11	0.9800
C1—C2	1.391 (6)	C12—H12A	0.9600
C1—C6	1.412 (5)	C12—H12B	0.9600
C2—C3	1.399 (6)	C12—H12C	0.9600
C2—C8	1.445 (6)	C13—H13A	0.9600
C3—C4	1.356 (6)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.393 (6)

O1ⁱ—Ni1—O1	180.000 (1)	O2—C7—H7C	109.5
O1ⁱ—Ni1—N1ⁱ	90.38 (13)	H7A—C7—H7C	109.5
O1—Ni1—N1ⁱ	89.62 (13)	H7B—C7—H7C	109.5
O1ⁱ—Ni1—N1	89.62 (13)	N1—C8—C2	126.7 (4)
O1—Ni1—N1	90.38 (13)	N1—C8—H8	116.7
N1ⁱ—Ni1—N1	180.00 (17)	C2—C8—H8	116.7
C1—O1—Ni1	127.2 (3)	N1—C9—C10	112.9 (3)
C6—O2—C7	118.2 (4)	N1—C9—H9A	109.0
C8—N1—C9	115.0 (4)	C10—C9—H9A	109.0
C8—N1—Ni1	123.7 (3)	N1—C9—H9B	109.0
C9—N1—Ni1	121.4 (3)	C10—C9—H9B	109.0
C10—N2—C11	115.8 (3)	H9A—C9—H9B	107.8
C10—N2—H2A	108.3	N2—C10—C9	111.5 (3)
C11—N2—H2A	108.3	N2—C10—H10A	109.3
C10—N2—H2B	108.3	C9—C10—H10A	109.3
C11—N2—H2B	108.3	N2—C10—H10B	109.3
H2A—N2—H2B	107.4	C9—C10—H10B	109.3
O1—C1—C2	124.4 (4)	H10A—C10—H10B	108.0
O1—C1—C6	117.2 (4)	N2—C11—C12	110.4 (4)
C2—C1—C6	118.3 (4)	N2—C11—C13	108.8 (4)
C1—C2—C3	120.3 (4)	C12—C11—C13	113.0 (5)
C1—C2—C8	121.6 (4)	N2—C11—H11	108.2
C3—C2—C8	118.0 (4)	C12—C11—H11	108.2
C4—C3—C2	120.2 (4)	C13—C11—H11	108.2
C4—C3—H3	119.9	C11—C12—H12A	109.5
C2—C3—H3	119.9	C11—C12—H12B	109.5
C3—C4—C5	120.8 (4)	H12A—C12—H12B	109.5
C3—C4—H4	119.6	C11—C12—H12C	109.5
C5—C4—H4	119.6	H12A—C12—H12C	109.5
C6—C5—C4	119.6 (4)	H12B—C12—H12C	109.5
C6—C5—H5	120.2	C11—C13—H13A	109.5
C4—C5—H5	120.2	C11—C13—H13B	109.5
O2—C6—C5	125.9 (4)	H13A—C13—H13B	109.5
O2—C6—C1	113.4 (4)	C11—C13—H13C	109.5
C5—C6—C1	120.7 (4)	H13A—C13—H13C	109.5
O2—C7—H7A	109.5	H13B—C13—H13C	109.5
O2—C7—H7B	109.5	N3—C14—S1	175.4 (7)
H7A—C7—H7B	109.5

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2ⁱ	0.90	2.34	3.068 (5)	138
N2—H2B···O1ⁱ	0.90	1.88	2.664 (4)	145
N2—H2A···N3	0.90	2.13	2.983 (6)	158

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₃H₂₀N₂O₂)₂](NCS)₂
M_r	647.49
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.520 (2), 9.810 (3), 24.102 (3)
V (Å³)	3196.7 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.78
Crystal size (mm)	0.23 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.841, 0.860
No. of measured, independent and observed [I > 2σ(I)] reflections	24542, 3863, 1895
R_int	0.110
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.175, 1.01
No. of reflections	3863
No. of parameters	190
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.38

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2ⁱ	0.90	2.34	3.068 (5)	137.9
N2—H2B···O1ⁱ	0.90	1.88	2.664 (4)	145.2
N2—H2A···N3	0.90	2.13	2.983 (6)	157.6

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

The project was supported financially by Jilin Medical College.

References

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Volume 64| Part 4| April 2008| Pages m597-m598

doi:10.1107/S1600536808008052

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

Bis{2-[2-(iso­propyl­ammonio)ethyl­imino­meth­yl]-6-meth­oxy­phenolato}nickel(II) di­thio­cyanate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{2-[2-(isopropylammonio)ethyliminomethyl]-6-methoxyphenolato}nickel(II) dithiocyanate