{2-[2-(Ethyl-amino)ethyl-imino-meth-yl]-5-methoxy-phenolato}thio-cyanato-nickel(II).

In the title mononuclear nickel(II) complex, [Ni(C(12)H(17)N(2)O(2))(NCS)], the metal atom is four-coordinated in a tetra-hedrally distorted square-planar geometry by the phenolate O atom, the imine N atom and the amine N atom of the Schiff base ligand and by the N atom of a thio-cyanate ligand. In the crystal structure, centrosymmetrically related mol-ecules are linked into dimers through inter-molecular N-H⋯O hydrogen bonds. These dimers are further connected by inter-molecular C-H⋯S hydrogen bonds, forming chains running parallel to [101].

Related literature

For general background to nickel(II) complexes with Schiff bases, see: Campbell & Urbach (1973 ▶); Wallis & Cummings (1974 ▶); Polt et al. (2003 ▶); Mukhopadhyay et al. (2003 ▶). For the structures of related complexes, see: Montazerozohori et al. (2009 ▶); Zhu et al. (2004 ▶, 2006 ▶).

Experimental

Crystal data

[Ni(C12H17N2O2)(NCS)]

M = 338.07

Monoclinic,

a = 9.298 (7) Å

b = 19.679 (14) Å

c = 8.461 (7) Å

β = 111.716 (11)°

V = 1438.3 (19) Å3

Z = 4

Mo Kα radiation

μ = 1.50 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.725, T max = 0.754

6520 measured reflections

2500 independent reflections

1564 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.127

S = 1.08

2500 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.52 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536810002357/rz2410sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002357/rz2410Isup2.hkl

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

[Ni(C12H17N2O2)(NCS)]	F(000) = 704
Mr = 338.07	Dx = 1.561 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1958 reflections
a = 9.298 (7) Å	θ = 2.4–24.5°
b = 19.679 (14) Å	µ = 1.50 mm−1
c = 8.461 (7) Å	T = 298 K
β = 111.716 (11)°	Block, red
V = 1438.3 (19) Å3	0.23 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2500 independent reflections
Radiation source: fine-focus sealed tube	1564 reflections with I > 2σ(I)
graphite	Rint = 0.071
ω scan	θmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −10→11
Tmin = 0.725, Tmax = 0.754	k = −23→16
6520 measured reflections	l = −9→9

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.2075P] where P = (Fo2 + 2Fc2)/3
2500 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 0.40 e Å−3
1 restraint	Δρmin = −0.52 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
Ni1	0.66858 (7)	0.96690 (3)	0.04177 (8)	0.0404 (2)
N1	0.8603 (5)	0.9561 (2)	0.2264 (5)	0.0469 (11)
N2	0.5948 (5)	0.8919 (2)	0.1568 (6)	0.0493 (11)
N3	0.4937 (5)	0.9566 (2)	−0.1713 (6)	0.0522 (12)
O1	0.7312 (4)	1.04775 (15)	−0.0367 (4)	0.0453 (9)
O2	1.0527 (5)	1.2299 (2)	−0.0529 (5)	0.0685 (12)
S1	0.3559 (2)	0.90996 (10)	−0.4968 (2)	0.1057 (8)
C1	0.9916 (6)	1.0501 (2)	0.1607 (6)	0.0430 (13)
C2	0.8670 (6)	1.0760 (3)	0.0252 (6)	0.0401 (12)
C3	0.8866 (6)	1.1367 (2)	−0.0506 (6)	0.0459 (13)
H3	0.8042	1.1550	−0.1406	0.055*
C4	1.0268 (7)	1.1694 (3)	0.0070 (7)	0.0501 (14)
C5	1.1530 (7)	1.1415 (3)	0.1362 (7)	0.0557 (15)
H5	1.2489	1.1629	0.1717	0.067*
C6	1.1350 (6)	1.0835 (3)	0.2092 (7)	0.0516 (14)
H6	1.2202	1.0646	0.2947	0.062*
C7	0.9819 (7)	0.9921 (3)	0.2524 (6)	0.0475 (13)
H7	1.0719	0.9784	0.3402	0.057*
C8	0.8622 (6)	0.8990 (2)	0.3367 (6)	0.0534 (15)
H8A	0.9347	0.9074	0.4515	0.064*
H8B	0.8929	0.8577	0.2949	0.064*
C9	0.7018 (6)	0.8923 (3)	0.3346 (7)	0.0562 (15)
H9A	0.6919	0.8504	0.3903	0.067*
H9B	0.6784	0.9300	0.3947	0.067*
C10	0.5750 (7)	0.8253 (3)	0.0735 (8)	0.0659 (17)
H10A	0.6760	0.8084	0.0835	0.079*
H10B	0.5144	0.8312	−0.0467	0.079*
C11	0.4994 (8)	0.7737 (3)	0.1418 (11)	0.112 (3)
H11A	0.5622	0.7648	0.2586	0.168*
H11B	0.4869	0.7326	0.0770	0.168*
H11C	0.3998	0.7900	0.1342	0.168*
C12	0.9247 (8)	1.2632 (3)	−0.1721 (8)	0.080 (2)
H12A	0.8835	1.2361	−0.2733	0.120*
H12B	0.9566	1.3065	−0.1999	0.120*
H12C	0.8466	1.2698	−0.1247	0.120*
C13	0.4377 (6)	0.9358 (3)	−0.3067 (8)	0.0506 (14)
H2	0.507 (4)	0.908 (3)	0.164 (7)	0.080*

	U11	U22	U33	U12	U13	U23
Ni1	0.0370 (4)	0.0427 (4)	0.0389 (4)	−0.0023 (3)	0.0108 (3)	0.0030 (3)
N1	0.046 (3)	0.051 (3)	0.046 (3)	0.007 (2)	0.021 (2)	0.009 (2)
N2	0.045 (3)	0.049 (3)	0.052 (3)	0.002 (2)	0.016 (2)	0.001 (2)
N3	0.046 (3)	0.061 (3)	0.048 (3)	−0.009 (2)	0.017 (2)	0.004 (2)
O1	0.038 (2)	0.049 (2)	0.045 (2)	0.0006 (17)	0.0100 (17)	0.0081 (15)
O2	0.066 (3)	0.070 (3)	0.077 (3)	−0.021 (2)	0.036 (3)	0.003 (2)
S1	0.1060 (17)	0.1090 (16)	0.0647 (12)	0.0371 (12)	−0.0118 (11)	−0.0307 (10)
C1	0.047 (4)	0.047 (3)	0.037 (3)	0.005 (3)	0.018 (3)	−0.004 (2)
C2	0.033 (3)	0.052 (3)	0.039 (3)	−0.002 (3)	0.018 (3)	−0.007 (2)
C3	0.045 (3)	0.050 (3)	0.049 (3)	0.002 (3)	0.024 (3)	0.004 (2)
C4	0.058 (4)	0.054 (3)	0.051 (4)	−0.005 (3)	0.036 (3)	−0.001 (3)
C5	0.043 (4)	0.077 (4)	0.056 (4)	−0.015 (3)	0.028 (3)	−0.008 (3)
C6	0.037 (3)	0.071 (4)	0.050 (3)	0.001 (3)	0.019 (3)	−0.006 (3)
C7	0.040 (3)	0.057 (3)	0.045 (3)	0.007 (3)	0.014 (3)	−0.005 (3)
C8	0.059 (4)	0.048 (3)	0.046 (3)	0.004 (3)	0.011 (3)	0.007 (2)
C9	0.057 (4)	0.064 (4)	0.049 (4)	0.001 (3)	0.020 (3)	0.011 (3)
C10	0.067 (4)	0.053 (4)	0.076 (4)	−0.010 (3)	0.024 (4)	−0.001 (3)
C11	0.099 (6)	0.053 (4)	0.213 (9)	−0.003 (4)	0.092 (6)	0.008 (5)
C12	0.095 (5)	0.067 (4)	0.087 (5)	−0.015 (4)	0.044 (5)	0.019 (4)
C13	0.043 (4)	0.050 (3)	0.053 (4)	0.011 (3)	0.011 (3)	0.002 (3)

Ni1—O1	1.897 (3)	C4—C5	1.387 (7)
Ni1—N1	1.898 (4)	C5—C6	1.338 (7)
Ni1—N3	1.940 (5)	C5—H5	0.9300
Ni1—N2	2.023 (5)	C6—H6	0.9300
N1—C7	1.281 (6)	C7—H7	0.9300
N1—C8	1.457 (6)	C8—C9	1.491 (7)
N2—C9	1.465 (6)	C8—H8A	0.9700
N2—C10	1.467 (7)	C8—H8B	0.9700
N2—H2	0.90 (5)	C9—H9A	0.9700
N3—C13	1.144 (6)	C9—H9B	0.9700
O1—C2	1.299 (5)	C10—C11	1.469 (8)
O2—C4	1.351 (6)	C10—H10A	0.9700
O2—C12	1.405 (7)	C10—H10B	0.9700
S1—C13	1.588 (6)	C11—H11A	0.9600
C1—C2	1.391 (7)	C11—H11B	0.9600
C1—C7	1.403 (7)	C11—H11C	0.9600
C1—C6	1.404 (7)	C12—H12A	0.9600
C2—C3	1.399 (7)	C12—H12B	0.9600
C3—C4	1.371 (7)	C12—H12C	0.9600
C3—H3	0.9300
O1—Ni1—N1	93.75 (17)	C1—C6—H6	119.0
O1—Ni1—N3	91.31 (16)	N1—C7—C1	126.0 (5)
N1—Ni1—N3	164.13 (18)	N1—C7—H7	117.0
O1—Ni1—N2	169.56 (16)	C1—C7—H7	117.0
N1—Ni1—N2	84.54 (18)	N1—C8—C9	106.6 (4)
N3—Ni1—N2	93.08 (18)	N1—C8—H8A	110.4
C7—N1—C8	121.0 (5)	C9—C8—H8A	110.4
C7—N1—Ni1	125.4 (4)	N1—C8—H8B	110.4
C8—N1—Ni1	113.5 (3)	C9—C8—H8B	110.4
C9—N2—C10	114.5 (4)	H8A—C8—H8B	108.6
C9—N2—Ni1	105.5 (3)	N2—C9—C8	108.0 (4)
C10—N2—Ni1	115.2 (4)	N2—C9—H9A	110.1
C9—N2—H2	103 (4)	C8—C9—H9A	110.1
C10—N2—H2	113 (4)	N2—C9—H9B	110.1
Ni1—N2—H2	105 (4)	C8—C9—H9B	110.1
C13—N3—Ni1	151.9 (5)	H9A—C9—H9B	108.4
C2—O1—Ni1	126.6 (3)	N2—C10—C11	114.9 (6)
C4—O2—C12	117.3 (5)	N2—C10—H10A	108.5
C2—C1—C7	123.4 (5)	C11—C10—H10A	108.5
C2—C1—C6	118.8 (5)	N2—C10—H10B	108.5
C7—C1—C6	117.9 (5)	C11—C10—H10B	108.5
O1—C2—C1	124.4 (5)	H10A—C10—H10B	107.5
O1—C2—C3	116.9 (5)	C10—C11—H11A	109.5
C1—C2—C3	118.7 (5)	C10—C11—H11B	109.5
C4—C3—C2	120.4 (5)	H11A—C11—H11B	109.5
C4—C3—H3	119.8	C10—C11—H11C	109.5
C2—C3—H3	119.8	H11A—C11—H11C	109.5
O2—C4—C3	123.9 (5)	H11B—C11—H11C	109.5
O2—C4—C5	115.4 (5)	O2—C12—H12A	109.5
C3—C4—C5	120.7 (5)	O2—C12—H12B	109.5
C6—C5—C4	119.2 (5)	H12A—C12—H12B	109.5
C6—C5—H5	120.4	O2—C12—H12C	109.5
C4—C5—H5	120.4	H12A—C12—H12C	109.5
C5—C6—C1	122.1 (5)	H12B—C12—H12C	109.5
C5—C6—H6	119.0	N3—C13—S1	177.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (5)	2.25 (3)	3.059 (6)	150 (5)
C7—H7···S1ii	0.93	2.83	3.708 (6)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.90 (5)	2.25 (3)	3.059 (6)	150 (5)
C7—H7⋯S1ii	0.93	2.83	3.708 (6)	158

Symmetry codes: (i) ; (ii) .