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

In the title mononuclear complex, [Ni(C(13)H(19)N(2)O(2))(NCS)], the Ni(II) ion is coordinated by one phenolate O atom, one imine N atom, and one amine N atom of a 2-[2-(isopropyl-amino)-ethyl-imino-meth-yl]-5-meth-oxy-phenolate Schiff base ligand, and by one N atom of a thio-cyanate ligand, forming a slightly distorted square-planar geometry.

Related literature

For background to the study of complexes with Schiff bases, see: Hamaker et al. (2010 ▶); Wang et al. (2010 ▶); Mirkhani et al. (2010 ▶); Liu & Yang (2009 ▶); Keypour et al. (2009 ▶); Adhikary et al. (2009 ▶); Peng et al. (2009 ▶). For related nickel complexes, see: Wang & Wei (2006 ▶); Wang (2007 ▶); Arıcı et al. (1999 ▶).

Experimental

Crystal data

[Ni(C13H19N2O2)(NCS)]

M = 352.09

Monoclinic,

a = 12.5653 (10) Å

b = 11.5197 (9) Å

c = 12.6916 (10) Å

β = 119.393 (4)°

V = 1600.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.35 mm−1

T = 298 K

0.25 × 0.23 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.729, T max = 0.756

9225 measured reflections

3458 independent reflections

2494 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.160

S = 1.07

3458 reflections

196 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.75 e Å−3

Δρmin = −0.60 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/S1600536810027236/lh5081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027236/lh5081Isup2.hkl

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

[Ni(C13H19N2O2)(NCS)]	F(000) = 736
Mr = 352.09	Dx = 1.461 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2662 reflections
a = 12.5653 (10) Å	θ = 2.5–25.3°
b = 11.5197 (9) Å	µ = 1.35 mm−1
c = 12.6916 (10) Å	T = 298 K
β = 119.393 (4)°	Block, red
V = 1600.6 (2) Å3	0.25 × 0.23 × 0.22 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3458 independent reflections
Radiation source: fine-focus sealed tube	2494 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→16
Tmin = 0.729, Tmax = 0.756	k = −14→12
9225 measured reflections	l = −16→15

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0583P)2 + 2.8719P] where P = (Fo2 + 2Fc2)/3
3458 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.75 e Å−3
1 restraint	Δρmin = −0.60 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.94253 (5)	0.61180 (5)	0.55042 (5)	0.0531 (2)
N1	0.8398 (4)	0.6742 (3)	0.4000 (3)	0.0593 (10)
N2	1.0753 (4)	0.6959 (4)	0.5468 (4)	0.0646 (11)
N3	1.0554 (4)	0.5515 (4)	0.7021 (4)	0.0636 (11)
O1	0.8235 (3)	0.5227 (3)	0.5535 (3)	0.0610 (8)
O2	0.4509 (3)	0.3133 (4)	0.4042 (3)	0.0836 (12)
S1	1.24390 (18)	0.4763 (2)	0.92183 (14)	0.1086 (7)
C1	0.6645 (4)	0.5528 (4)	0.3496 (4)	0.0545 (11)
C2	0.7132 (4)	0.5012 (4)	0.4638 (4)	0.0530 (11)
C3	0.6407 (4)	0.4205 (4)	0.4841 (4)	0.0560 (11)
H3	0.6705	0.3869	0.5600	0.067*
C4	0.5259 (5)	0.3910 (5)	0.3922 (5)	0.0639 (13)
C5	0.4792 (5)	0.4400 (6)	0.2774 (5)	0.0773 (16)
H5	0.4026	0.4186	0.2152	0.093*
C6	0.5467 (5)	0.5184 (5)	0.2584 (5)	0.0713 (15)
H6	0.5149	0.5517	0.1821	0.086*
C7	0.7299 (5)	0.6411 (4)	0.3259 (4)	0.0621 (13)
H7	0.6899	0.6777	0.2510	0.075*
C8	0.8943 (6)	0.7672 (5)	0.3645 (5)	0.0822 (17)
H8A	0.8816	0.8416	0.3925	0.099*
H8B	0.8581	0.7700	0.2772	0.099*
C9	1.0311 (6)	0.7397 (6)	0.4236 (5)	0.0834 (18)
H9A	1.0448	0.6818	0.3760	0.100*
H9B	1.0758	0.8093	0.4262	0.100*
C10	1.1434 (5)	0.7834 (5)	0.6505 (5)	0.0723 (15)
H10	1.1569	0.7437	0.7243	0.087*
C11	1.0702 (9)	0.8835 (7)	0.6392 (8)	0.131 (3)
H11A	1.1127	0.9315	0.7096	0.196*
H11B	0.9938	0.8590	0.6317	0.196*
H11C	1.0554	0.9269	0.5686	0.196*
C12	1.2673 (6)	0.8053 (8)	0.6660 (6)	0.107 (2)
H12A	1.2595	0.8362	0.5923	0.161*
H12B	1.3122	0.7338	0.6854	0.161*
H12C	1.3099	0.8601	0.7303	0.161*
C13	0.4892 (6)	0.2617 (6)	0.5198 (6)	0.093 (2)
H13A	0.5602	0.2146	0.5421	0.139*
H13B	0.4246	0.2142	0.5159	0.139*
H13C	0.5086	0.3216	0.5790	0.139*
C14	1.1335 (5)	0.5202 (5)	0.7934 (5)	0.0619 (12)
H2	1.138 (3)	0.645 (4)	0.570 (5)	0.080*

	U11	U22	U33	U12	U13	U23
Ni1	0.0558 (4)	0.0484 (3)	0.0500 (3)	−0.0051 (3)	0.0219 (3)	0.0044 (3)
N1	0.074 (3)	0.046 (2)	0.053 (2)	0.0041 (19)	0.028 (2)	0.0084 (17)
N2	0.077 (3)	0.053 (2)	0.072 (3)	−0.005 (2)	0.043 (2)	−0.005 (2)
N3	0.057 (2)	0.064 (3)	0.056 (2)	−0.006 (2)	0.018 (2)	0.006 (2)
O1	0.0469 (17)	0.074 (2)	0.0515 (17)	−0.0055 (16)	0.0156 (14)	0.0116 (16)
O2	0.065 (2)	0.101 (3)	0.075 (2)	−0.028 (2)	0.0270 (19)	−0.026 (2)
S1	0.1005 (13)	0.1439 (17)	0.0576 (8)	0.0531 (12)	0.0204 (8)	0.0087 (10)
C1	0.049 (2)	0.061 (3)	0.050 (2)	0.011 (2)	0.021 (2)	0.004 (2)
C2	0.048 (2)	0.058 (3)	0.052 (2)	0.008 (2)	0.023 (2)	−0.006 (2)
C3	0.052 (3)	0.063 (3)	0.051 (2)	−0.003 (2)	0.024 (2)	−0.002 (2)
C4	0.053 (3)	0.073 (3)	0.064 (3)	−0.005 (3)	0.028 (2)	−0.020 (3)
C5	0.052 (3)	0.097 (4)	0.061 (3)	0.005 (3)	0.011 (2)	−0.016 (3)
C6	0.063 (3)	0.084 (4)	0.053 (3)	0.009 (3)	0.017 (2)	0.005 (3)
C7	0.071 (3)	0.057 (3)	0.050 (3)	0.022 (2)	0.024 (2)	0.012 (2)
C8	0.112 (5)	0.059 (3)	0.074 (4)	−0.006 (3)	0.044 (3)	0.012 (3)
C9	0.104 (5)	0.076 (4)	0.072 (4)	−0.026 (3)	0.044 (3)	0.004 (3)
C10	0.082 (4)	0.058 (3)	0.078 (3)	−0.021 (3)	0.040 (3)	−0.010 (3)
C11	0.164 (8)	0.104 (6)	0.106 (6)	0.043 (6)	0.052 (5)	−0.027 (5)
C12	0.086 (5)	0.146 (7)	0.093 (5)	−0.027 (5)	0.047 (4)	−0.015 (5)
C13	0.086 (4)	0.110 (5)	0.085 (4)	−0.042 (4)	0.044 (4)	−0.022 (4)
C14	0.064 (3)	0.063 (3)	0.059 (3)	0.002 (2)	0.030 (3)	−0.006 (2)

Ni1—O1	1.830 (3)	C5—C6	1.340 (8)
Ni1—N1	1.846 (4)	C5—H5	0.9300
Ni1—N3	1.876 (4)	C6—H6	0.9300
Ni1—N2	1.949 (4)	C7—H7	0.9300
N1—C7	1.290 (6)	C8—C9	1.534 (8)
N1—C8	1.457 (7)	C8—H8A	0.9700
N2—C9	1.469 (7)	C8—H8B	0.9700
N2—C10	1.541 (6)	C9—H9A	0.9700
N2—H2	0.91 (5)	C9—H9B	0.9700
N3—C14	1.148 (6)	C10—C11	1.436 (9)
O1—C2	1.315 (5)	C10—C12	1.492 (8)
O2—C4	1.361 (6)	C10—H10	0.9800
O2—C13	1.430 (7)	C11—H11A	0.9600
S1—C14	1.618 (5)	C11—H11B	0.9600
C1—C2	1.400 (6)	C11—H11C	0.9600
C1—C6	1.416 (7)	C12—H12A	0.9600
C1—C7	1.429 (7)	C12—H12B	0.9600
C2—C3	1.411 (7)	C12—H12C	0.9600
C3—C4	1.380 (7)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.395 (8)	C13—H13C	0.9600
O1—Ni1—N1	94.39 (16)	C1—C7—H7	117.4
O1—Ni1—N3	89.12 (16)	N1—C8—C9	106.3 (4)
N1—Ni1—N3	176.32 (19)	N1—C8—H8A	110.5
O1—Ni1—N2	175.67 (17)	C9—C8—H8A	110.5
N1—Ni1—N2	87.39 (19)	N1—C8—H8B	110.5
N3—Ni1—N2	89.03 (19)	C9—C8—H8B	110.5
C7—N1—C8	119.3 (4)	H8A—C8—H8B	108.7
C7—N1—Ni1	126.5 (4)	N2—C9—C8	109.8 (5)
C8—N1—Ni1	114.2 (4)	N2—C9—H9A	109.7
C9—N2—C10	116.5 (4)	C8—C9—H9A	109.7
C9—N2—Ni1	108.3 (3)	N2—C9—H9B	109.7
C10—N2—Ni1	115.3 (3)	C8—C9—H9B	109.7
C9—N2—H2	113 (4)	H9A—C9—H9B	108.2
C10—N2—H2	97 (4)	C11—C10—C12	116.9 (7)
Ni1—N2—H2	106 (4)	C11—C10—N2	112.3 (5)
C14—N3—Ni1	173.1 (4)	C12—C10—N2	109.2 (5)
C2—O1—Ni1	127.7 (3)	C11—C10—H10	105.8
C4—O2—C13	119.0 (4)	C12—C10—H10	105.8
C2—C1—C6	118.6 (5)	N2—C10—H10	105.8
C2—C1—C7	121.1 (4)	C10—C11—H11A	109.5
C6—C1—C7	120.3 (4)	C10—C11—H11B	109.5
O1—C2—C1	123.8 (4)	H11A—C11—H11B	109.5
O1—C2—C3	117.8 (4)	C10—C11—H11C	109.5
C1—C2—C3	118.4 (4)	H11A—C11—H11C	109.5
C4—C3—C2	120.6 (5)	H11B—C11—H11C	109.5
C4—C3—H3	119.7	C10—C12—H12A	109.5
C2—C3—H3	119.7	C10—C12—H12B	109.5
O2—C4—C3	124.2 (5)	H12A—C12—H12B	109.5
O2—C4—C5	115.1 (5)	C10—C12—H12C	109.5
C3—C4—C5	120.8 (5)	H12A—C12—H12C	109.5
C6—C5—C4	118.8 (5)	H12B—C12—H12C	109.5
C6—C5—H5	120.6	O2—C13—H13A	109.5
C4—C5—H5	120.6	O2—C13—H13B	109.5
C5—C6—C1	122.8 (5)	H13A—C13—H13B	109.5
C5—C6—H6	118.6	O2—C13—H13C	109.5
C1—C6—H6	118.6	H13A—C13—H13C	109.5
N1—C7—C1	125.2 (4)	H13B—C13—H13C	109.5
N1—C7—H7	117.4	N3—C14—S1	179.7 (6)

Ni1—O1	1.830 (3)
Ni1—N1	1.846 (4)
Ni1—N3	1.876 (4)
Ni1—N2	1.949 (4)

O1—Ni1—N1	94.39 (16)
O1—Ni1—N3	89.12 (16)
N1—Ni1—N3	176.32 (19)
O1—Ni1—N2	175.67 (17)
N1—Ni1—N2	87.39 (19)
N3—Ni1—N2	89.03 (19)