{N,N'-Bis[1-(2-pyrid-yl)ethyl-idene]propane-1,2-diamine}-bis(thio-cyanato-κN)-nickel(II).

In the title complex, [Ni(NCS)(2)(C(17)H(20)N(4))], the Ni(2+) ion (site symmetry 2) is coordinated by the N,N,N,N-tetra-dentate Schiff base ligand and two thio-cyanate ligands, forming a distorted NiN(6) octa-hedral geometry, with the thio-cyanate N atoms in a trans orientation. The pendant methyl group of the central propane-1,2-diamine fragment of the ligand is statistically disordered over two sets of positions. In the crystal, weak aromatic π-π stacking between pyridine rings [centroid-centroid separation = 3.7081 (17) Å] may help to establish the packing.

Related literature

For background to bis-Schiff bases in coordination chemistry, see: Yin et al. (1999 ▶); Costes et al. (2002 ▶); Haikarainen et al. (2001 ▶); Miyasaka et al. (2002 ▶); Ryaza­nov et al. (2002 ▶). For nickel complexes with Schiff bases, see: Liu et al. (2006 ▶); Li & Wang (2007 ▶); Liu et al. (2007 ▶); Ali et al. (2006 ▶); Knight et al. (2007 ▶).

Experimental

Crystal data

[Ni(NCS)2(C17H20N4)]

M = 455.24

Monoclinic,

a = 12.431 (2) Å

b = 12.805 (2) Å

c = 13.613 (3) Å

β = 102.741 (2)°

V = 2113.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.13 mm−1

T = 298 K

0.27 × 0.25 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.750, T max = 0.781

8183 measured reflections

2311 independent reflections

1982 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.088

S = 1.09

2311 reflections

140 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029454/hb5571sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029454/hb5571Isup2.hkl

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

[Ni(NCS)2(C17H20N4)]	F(000) = 944
Mr = 455.24	Dx = 1.431 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.431 (2) Å	Cell parameters from 2917 reflections
b = 12.805 (2) Å	θ = 2.3–25.0°
c = 13.613 (3) Å	µ = 1.13 mm−1
β = 102.741 (2)°	T = 298 K
V = 2113.5 (7) Å3	Block, green
Z = 4	0.27 × 0.25 × 0.23 mm

Bruker APEXII CCD diffractometer	2311 independent reflections
Radiation source: fine-focus sealed tube	1982 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −15→15
Tmin = 0.750, Tmax = 0.781	k = −16→16
8183 measured reflections	l = −17→17

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0271P)2 + 3.1898P] where P = (Fo2 + 2Fc2)/3
2311 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.46 e Å−3
3 restraints	Δρmin = −0.42 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	Occ. (<1)
Ni1	0.0000	0.18939 (3)	0.2500	0.03735 (14)
S1	0.36209 (7)	0.21125 (8)	0.18060 (8)	0.0830 (3)
N1	0.06978 (16)	0.10959 (15)	0.38468 (15)	0.0409 (5)
N2	0.03606 (17)	0.30853 (15)	0.34856 (15)	0.0428 (5)
N3	0.15474 (19)	0.18115 (19)	0.21915 (17)	0.0552 (6)
C1	0.0951 (2)	0.0091 (2)	0.3988 (2)	0.0497 (6)
H1	0.0766	−0.0361	0.3442	0.060*
C2	0.1477 (2)	−0.0311 (2)	0.4910 (2)	0.0593 (7)
H2	0.1657	−0.1016	0.4980	0.071*
C3	0.1726 (3)	0.0348 (2)	0.5717 (2)	0.0652 (8)
H3	0.2066	0.0094	0.6349	0.078*
C4	0.1469 (2)	0.1393 (2)	0.5586 (2)	0.0568 (7)
H4	0.1631	0.1851	0.6129	0.068*
C5	0.0970 (2)	0.17503 (19)	0.46397 (18)	0.0419 (5)
C6	0.0706 (2)	0.28796 (19)	0.44138 (18)	0.0432 (6)
C7	0.0860 (3)	0.3646 (2)	0.5261 (2)	0.0633 (8)
H7A	0.0774	0.4343	0.4995	0.095*
H7B	0.1585	0.3568	0.5681	0.095*
H7C	0.0318	0.3521	0.5653	0.095*
C8	−0.0029 (3)	0.41034 (19)	0.3058 (2)	0.0511 (6)
C9	−0.1228 (5)	0.4304 (5)	0.3185 (5)	0.0575 (15)	0.50
H9A	−0.1718	0.3803	0.2794	0.086*	0.50
H9B	−0.1453	0.4995	0.2957	0.086*	0.50
H9C	−0.1252	0.4236	0.3882	0.086*	0.50
C10	0.2400 (2)	0.1951 (2)	0.20181 (18)	0.0475 (6)
H8A	0.0431 (18)	0.4673 (15)	0.3394 (18)	0.057*
H8B	−0.0770 (17)	0.425 (4)	0.313 (6)	0.057*	0.50

	U11	U22	U33	U12	U13	U23
Ni1	0.0420 (3)	0.0318 (2)	0.0380 (2)	0.000	0.00829 (18)	0.000
S1	0.0502 (5)	0.1068 (8)	0.0979 (7)	−0.0146 (4)	0.0290 (5)	−0.0109 (5)
N1	0.0403 (11)	0.0382 (11)	0.0443 (11)	0.0025 (8)	0.0097 (9)	0.0035 (9)
N2	0.0512 (12)	0.0345 (10)	0.0419 (11)	0.0027 (9)	0.0086 (9)	−0.0015 (9)
N3	0.0495 (13)	0.0646 (15)	0.0532 (13)	−0.0075 (11)	0.0152 (11)	−0.0068 (11)
C1	0.0534 (15)	0.0383 (13)	0.0572 (16)	0.0031 (11)	0.0120 (12)	0.0031 (11)
C2	0.0607 (18)	0.0464 (15)	0.0686 (19)	0.0037 (13)	0.0094 (15)	0.0175 (14)
C3	0.070 (2)	0.0642 (19)	0.0554 (17)	−0.0016 (15)	0.0001 (15)	0.0204 (15)
C4	0.0646 (18)	0.0579 (17)	0.0450 (15)	−0.0044 (14)	0.0060 (13)	0.0068 (13)
C5	0.0413 (13)	0.0437 (13)	0.0412 (13)	−0.0012 (10)	0.0104 (10)	0.0029 (10)
C6	0.0464 (14)	0.0425 (13)	0.0418 (13)	−0.0003 (10)	0.0121 (11)	−0.0029 (10)
C7	0.091 (2)	0.0538 (17)	0.0455 (15)	0.0042 (16)	0.0152 (15)	−0.0087 (13)
C8	0.0694 (18)	0.0326 (12)	0.0490 (15)	0.0042 (12)	0.0083 (14)	−0.0008 (11)
C9	0.069 (4)	0.038 (3)	0.059 (3)	0.007 (3)	0.001 (3)	−0.008 (2)
C10	0.0474 (15)	0.0542 (15)	0.0393 (13)	−0.0041 (12)	0.0063 (11)	−0.0061 (11)

Ni1—N2	2.0157 (19)	C3—H3	0.9300
Ni1—N2i	2.0157 (19)	C4—C5	1.379 (3)
Ni1—N3i	2.060 (2)	C4—H4	0.9300
Ni1—N3	2.060 (2)	C5—C6	1.499 (3)
Ni1—N1i	2.111 (2)	C6—C7	1.495 (3)
Ni1—N1	2.111 (2)	C7—H7A	0.9600
S1—C10	1.620 (3)	C7—H7B	0.9600
N1—C1	1.329 (3)	C7—H7C	0.9600
N1—C5	1.349 (3)	C8—C8i	1.536 (5)
N2—C6	1.269 (3)	C8—C9	1.560 (6)
N2—C8	1.466 (3)	C8—H8A	0.976 (10)
N3—C10	1.149 (3)	C8—H8B	0.967 (10)
C1—C2	1.380 (4)	C9—H9A	0.9600
C1—H1	0.9300	C9—H9B	0.9600
C2—C3	1.365 (4)	C9—H9C	0.9600
C2—H2	0.9300	C9—H8B	0.594 (13)
C3—C4	1.378 (4)
N2—Ni1—N2i	81.62 (11)	N1—C5—C4	121.5 (2)
N2—Ni1—N3i	89.07 (9)	N1—C5—C6	115.5 (2)
N2i—Ni1—N3i	95.39 (9)	C4—C5—C6	123.0 (2)
N2—Ni1—N3	95.39 (9)	N2—C6—C7	126.1 (2)
N2i—Ni1—N3	89.07 (9)	N2—C6—C5	114.5 (2)
N3i—Ni1—N3	174.13 (14)	C7—C6—C5	119.4 (2)
N2—Ni1—N1i	158.89 (8)	C6—C7—H7A	109.5
N2i—Ni1—N1i	78.45 (8)	C6—C7—H7B	109.5
N3i—Ni1—N1i	85.93 (9)	H7A—C7—H7B	109.5
N3—Ni1—N1i	91.23 (8)	C6—C7—H7C	109.5
N2—Ni1—N1	78.45 (8)	H7A—C7—H7C	109.5
N2i—Ni1—N1	158.89 (8)	H7B—C7—H7C	109.5
N3i—Ni1—N1	91.23 (8)	N2—C8—C8i	108.03 (17)
N3—Ni1—N1	85.93 (8)	N2—C8—C9	110.0 (3)
N1i—Ni1—N1	122.10 (11)	C8i—C8—C9	111.3 (4)
C1—N1—C5	118.5 (2)	N2—C8—H8A	111.8 (16)
C1—N1—Ni1	129.29 (18)	C8i—C8—H8A	108.2 (16)
C5—N1—Ni1	112.12 (15)	C9—C8—H8A	107.5 (16)
C6—N2—C8	126.1 (2)	N2—C8—H8B	112 (4)
C6—N2—Ni1	118.83 (17)	C8i—C8—H8B	111 (5)
C8—N2—Ni1	113.78 (15)	C9—C8—H8B	2(4)
C10—N3—Ni1	168.1 (2)	H8A—C8—H8B	106 (2)
N1—C1—C2	122.8 (3)	C8—C9—H9A	109.5
N1—C1—H1	118.6	C8—C9—H9B	109.5
C2—C1—H1	118.6	H9A—C9—H9B	109.5
C3—C2—C1	118.6 (3)	C8—C9—H9C	109.5
C3—C2—H2	120.7	H9A—C9—H9C	109.5
C1—C2—H2	120.7	H9B—C9—H9C	109.5
C2—C3—C4	119.4 (3)	C8—C9—H8B	3(7)
C2—C3—H3	120.3	H9A—C9—H8B	111.4
C4—C3—H3	120.3	H9B—C9—H8B	106.2
C3—C4—C5	119.2 (3)	H9C—C9—H8B	110.7
C3—C4—H4	120.4	N3—C10—S1	177.8 (3)
C5—C4—H4	120.4

Ni1—N2	2.0157 (19)
Ni1—N3	2.060 (2)
Ni1—N1	2.111 (2)

N2—Ni1—N2i	81.62 (11)
N2—Ni1—N3i	89.07 (9)
N2—Ni1—N3	95.39 (9)
N2—Ni1—N1i	158.89 (8)
N3—Ni1—N1i	91.23 (8)
N2—Ni1—N1	78.45 (8)
N3—Ni1—N1	85.93 (8)

Symmetry code: (i) .