Bis{2-[2-(isopropyl-ammonio)ethyl-imino-meth-yl]-6-methoxy-phenolato}nickel(II) dithio-cyanate.

The title complex, [Ni(C(13)H(20)N(2)O(2))(2)](NCS)(2), consists of a centrosymmetric mononuclear four-coordinate nickel(II) complex cation and two thio-cyanate 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 meth-oxy O atoms of the ligand, and in N-H⋯N hydrogen bonds with the N atoms of the thio-cyanate 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 = 647.49

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.175

S = 1.01

3863 reflections

190 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.38 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008052/su2049sup1.cif

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

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

[Ni(C13H20N2O2)2](NCS)2	Dx = 1.345 Mg m−3
Mr = 647.49	Mo Kα radiation λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1440 reflections
a = 13.520 (2) Å	θ = 2.3–24.6º
b = 9.810 (3) Å	µ = 0.78 mm−1
c = 24.102 (3) Å	T = 298 (2) K
V = 3196.7 (12) Å3	Block, red
Z = 4	0.23 × 0.22 × 0.20 mm
F000 = 1368

Bruker SMART CCD area-detector diffractometer	3863 independent reflections
Radiation source: fine-focus sealed tube	1895 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.110
T = 298(2) K	θmax = 28.3º
ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −17→17
Tmin = 0.841, Tmax = 0.860	k = −12→12
24542 measured reflections	l = −31→31

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.070	H-atom parameters constrained
wR(F2) = 0.175	w = 1/[σ2(Fo2) + (0.0594P)2 + 2.0547P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3863 reflections	Δρmax = 0.29 e Å−3
190 parameters	Δρmin = −0.38 e Å−3
6 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
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)

	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)

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

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

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) .