{5-Meth-oxy-2-[(2-morpholinoethyl)-iminometh-yl]phenolato}(thio-cyanato-κN)-nickel(II).

In the mononuclear title complex, [Ni(C(14)H(19)N(2)O(3))(NCS)], the nickel(II) atom is four-coordinated in a square-planar geometry by the O and N atoms of the tridentate Schiff base ligand and by the N atom of a thio-cyanate ligand. The crystal structure is stabilized by inter-molecular C-H⋯S and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For general background to nickel(II) complexes with n class="Chemical">Schiff bases, see: Campbell & Urbach (1973 ▶); Wallis & Cummings (1974 ▶); Polt et al. (2003 ▶); Mukhopadhyay et al. (2003 ▶). For related structures, see: Liu (2010 ▶); Montazerozohori et al. (2009 ▶); Zhu et al. (2004 ▶, 2006 ▶).

Experimental

Crystal data

[Ni(C14H19N2O3)(n class="Chemical">NCS)]

M = 380.10

Monoclinic,

a = 12.3983 (18) Å

b = 11.8202 (17) Å

c = 12.2913 (18) Å

β = 114.756 (2)°

V = 1635.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.33 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.777, T max = 0.796

9279 measured reflections

3554 independent reflections

2729 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.03

3554 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.38 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/S160053681000468X/rz2416sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000468X/rz2416Isup2.hkl

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

[Ni(C14H19N2O3)(NCS)]	F(000) = 792
Mr = 380.10	Dx = 1.543 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2524 reflections
a = 12.3983 (18) Å	θ = 2.5–25.6°
b = 11.8202 (17) Å	µ = 1.33 mm−1
c = 12.2913 (18) Å	T = 298 K
β = 114.756 (2)°	Block, red
V = 1635.8 (4) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3554 independent reflections
Radiation source: fine-focus sealed tube	2729 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scan	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.777, Tmax = 0.796	k = −7→15
9279 measured reflections	l = −15→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0433P)2 + 0.1781P] where P = (Fo2 + 2Fc2)/3
3554 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.38 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 > 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	0.08568 (2)	0.38142 (2)	0.14197 (3)	0.03183 (11)
O1	0.19256 (14)	0.46933 (15)	0.26251 (14)	0.0392 (4)
O2	0.53990 (16)	0.69070 (18)	0.46786 (17)	0.0579 (5)
O3	−0.24289 (16)	0.14271 (16)	−0.05535 (17)	0.0499 (5)
S1	−0.23786 (6)	0.53989 (8)	0.18241 (7)	0.0594 (2)
N1	0.19869 (17)	0.32497 (18)	0.09614 (18)	0.0377 (5)
N2	−0.02732 (16)	0.27875 (16)	0.02024 (16)	0.0334 (4)
N3	−0.03493 (18)	0.44345 (18)	0.17904 (19)	0.0426 (5)
C1	0.3595 (2)	0.4495 (2)	0.2126 (2)	0.0393 (6)
C2	0.3021 (2)	0.4969 (2)	0.2800 (2)	0.0345 (5)
C3	0.3625 (2)	0.5777 (2)	0.3677 (2)	0.0385 (6)
H3	0.3264	0.6089	0.4135	0.046*
C4	0.4760 (2)	0.6113 (2)	0.3864 (2)	0.0435 (6)
C5	0.5327 (2)	0.5647 (3)	0.3200 (3)	0.0542 (8)
H5	0.6090	0.5878	0.3335	0.065*
C6	0.4760 (2)	0.4856 (3)	0.2358 (3)	0.0529 (7)
H6	0.5143	0.4543	0.1921	0.064*
C7	0.3061 (2)	0.3638 (2)	0.1276 (2)	0.0428 (6)
H7	0.3510	0.3321	0.0909	0.051*
C8	0.1593 (2)	0.2292 (2)	0.0126 (3)	0.0496 (7)
H8A	0.1724	0.1583	0.0560	0.060*
H8B	0.2023	0.2274	−0.0376	0.060*
C9	0.0292 (2)	0.2477 (2)	−0.0620 (2)	0.0472 (7)
H9A	0.0177	0.3079	−0.1194	0.057*
H9B	−0.0067	0.1792	−0.1057	0.057*
C10	−0.0414 (2)	0.1787 (2)	0.0893 (2)	0.0375 (6)
H10A	−0.0668	0.2055	0.1495	0.045*
H10B	0.0351	0.1422	0.1306	0.045*
C11	−0.1300 (2)	0.0925 (2)	0.0110 (2)	0.0457 (6)
H11A	−0.1010	0.0594	−0.0439	0.055*
H11B	−0.1381	0.0323	0.0608	0.055*
C12	−0.2340 (2)	0.2320 (2)	−0.1291 (2)	0.0500 (7)
H12A	−0.3120	0.2644	−0.1744	0.060*
H12B	−0.2052	0.2021	−0.1855	0.060*
C13	−0.1501 (2)	0.3231 (2)	−0.0532 (2)	0.0450 (7)
H13A	−0.1456	0.3830	−0.1051	0.054*
H13B	−0.1817	0.3555	−0.0001	0.054*
C14	−0.1188 (2)	0.4842 (2)	0.1815 (2)	0.0378 (6)
C15	0.4866 (3)	0.7462 (3)	0.5363 (3)	0.0716 (10)
H15A	0.4169	0.7862	0.4833	0.107*
H15B	0.5421	0.7988	0.5907	0.107*
H15C	0.4648	0.6911	0.5808	0.107*

	U11	U22	U33	U12	U13	U23
Ni1	0.02692 (17)	0.03345 (18)	0.03502 (18)	−0.00070 (13)	0.01288 (13)	−0.00172 (14)
O1	0.0278 (8)	0.0510 (11)	0.0406 (9)	−0.0070 (8)	0.0160 (7)	−0.0087 (8)
O2	0.0449 (11)	0.0704 (14)	0.0562 (12)	−0.0265 (10)	0.0191 (10)	−0.0103 (11)
O3	0.0369 (10)	0.0518 (11)	0.0553 (11)	−0.0091 (9)	0.0137 (9)	0.0012 (9)
S1	0.0378 (4)	0.0820 (6)	0.0614 (5)	0.0141 (4)	0.0236 (4)	−0.0038 (4)
N1	0.0352 (11)	0.0367 (11)	0.0437 (12)	0.0009 (10)	0.0191 (10)	−0.0043 (10)
N2	0.0334 (10)	0.0337 (11)	0.0327 (10)	−0.0013 (9)	0.0134 (9)	0.0018 (9)
N3	0.0310 (11)	0.0456 (13)	0.0508 (13)	−0.0024 (10)	0.0167 (10)	−0.0102 (11)
C1	0.0289 (12)	0.0427 (15)	0.0472 (15)	0.0005 (11)	0.0167 (11)	−0.0002 (12)
C2	0.0273 (12)	0.0379 (13)	0.0379 (13)	0.0005 (11)	0.0134 (10)	0.0079 (11)
C3	0.0337 (13)	0.0445 (14)	0.0371 (13)	−0.0046 (12)	0.0146 (11)	0.0019 (12)
C4	0.0334 (13)	0.0514 (16)	0.0389 (14)	−0.0097 (13)	0.0083 (11)	0.0047 (13)
C5	0.0308 (13)	0.066 (2)	0.0664 (19)	−0.0087 (14)	0.0213 (14)	−0.0015 (16)
C6	0.0359 (14)	0.0619 (18)	0.0669 (18)	−0.0026 (14)	0.0274 (14)	−0.0084 (16)
C7	0.0354 (13)	0.0467 (16)	0.0521 (16)	0.0054 (12)	0.0240 (13)	−0.0019 (13)
C8	0.0513 (16)	0.0465 (16)	0.0613 (17)	−0.0045 (14)	0.0337 (14)	−0.0153 (14)
C9	0.0575 (17)	0.0485 (16)	0.0409 (14)	−0.0134 (14)	0.0260 (13)	−0.0090 (13)
C10	0.0371 (13)	0.0365 (13)	0.0369 (13)	0.0031 (11)	0.0134 (11)	0.0073 (11)
C11	0.0504 (16)	0.0358 (14)	0.0523 (16)	−0.0048 (13)	0.0229 (14)	0.0030 (12)
C12	0.0429 (15)	0.0519 (17)	0.0408 (15)	−0.0032 (14)	0.0034 (12)	0.0020 (13)
C13	0.0412 (14)	0.0381 (14)	0.0402 (14)	0.0031 (12)	0.0018 (12)	0.0064 (12)
C14	0.0351 (13)	0.0406 (14)	0.0373 (13)	−0.0026 (12)	0.0148 (11)	−0.0042 (11)
C15	0.066 (2)	0.086 (2)	0.065 (2)	−0.037 (2)	0.0303 (18)	−0.0246 (19)

Ni1—N1	1.840 (2)	C5—C6	1.353 (4)
Ni1—O1	1.8402 (16)	C5—H5	0.9300
Ni1—N3	1.885 (2)	C6—H6	0.9300
Ni1—N2	1.9796 (19)	C7—H7	0.9300
O1—C2	1.323 (3)	C8—C9	1.500 (4)
O2—C4	1.359 (3)	C8—H8A	0.9700
O2—C15	1.429 (4)	C8—H8B	0.9700
O3—C11	1.421 (3)	C9—H9A	0.9700
O3—C12	1.425 (3)	C9—H9B	0.9700
S1—C14	1.621 (3)	C10—C11	1.512 (3)
N1—C7	1.304 (3)	C10—H10A	0.9700
N1—C8	1.468 (3)	C10—H10B	0.9700
N2—C9	1.497 (3)	C11—H11A	0.9700
N2—C13	1.502 (3)	C11—H11B	0.9700
N2—C10	1.508 (3)	C12—C13	1.517 (3)
N3—C14	1.158 (3)	C12—H12A	0.9700
C1—C7	1.406 (3)	C12—H12B	0.9700
C1—C2	1.414 (3)	C13—H13A	0.9700
C1—C6	1.415 (3)	C13—H13B	0.9700
C2—C3	1.400 (3)	C15—H15A	0.9600
C3—C4	1.385 (3)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.394 (4)
N1—Ni1—O1	93.86 (8)	C9—C8—H8A	110.6
N1—Ni1—N3	176.31 (9)	N1—C8—H8B	110.6
O1—Ni1—N3	87.85 (8)	C9—C8—H8B	110.6
N1—Ni1—N2	86.27 (8)	H8A—C8—H8B	108.7
O1—Ni1—N2	176.19 (8)	N2—C9—C8	108.1 (2)
N3—Ni1—N2	92.24 (8)	N2—C9—H9A	110.1
C2—O1—Ni1	127.84 (15)	C8—C9—H9A	110.1
C4—O2—C15	118.7 (2)	N2—C9—H9B	110.1
C11—O3—C12	110.8 (2)	C8—C9—H9B	110.1
C7—N1—C8	118.6 (2)	H9A—C9—H9B	108.4
C7—N1—Ni1	126.50 (18)	N2—C10—C11	113.25 (19)
C8—N1—Ni1	114.88 (15)	N2—C10—H10A	108.9
C9—N2—C13	108.85 (19)	C11—C10—H10A	108.9
C9—N2—C10	112.65 (19)	N2—C10—H10B	108.9
C13—N2—C10	106.55 (18)	C11—C10—H10B	108.9
C9—N2—Ni1	106.12 (14)	H10A—C10—H10B	107.7
C13—N2—Ni1	117.30 (15)	O3—C11—C10	111.2 (2)
C10—N2—Ni1	105.51 (13)	O3—C11—H11A	109.4
C14—N3—Ni1	168.7 (2)	C10—C11—H11A	109.4
C7—C1—C2	121.6 (2)	O3—C11—H11B	109.4
C7—C1—C6	119.4 (2)	C10—C11—H11B	109.4
C2—C1—C6	119.0 (2)	H11A—C11—H11B	108.0
O1—C2—C3	118.4 (2)	O3—C12—C13	110.5 (2)
O1—C2—C1	122.8 (2)	O3—C12—H12A	109.5
C3—C2—C1	118.8 (2)	C13—C12—H12A	109.5
C4—C3—C2	120.2 (2)	O3—C12—H12B	109.5
C4—C3—H3	119.9	C13—C12—H12B	109.5
C2—C3—H3	119.9	H12A—C12—H12B	108.1
O2—C4—C3	123.9 (3)	N2—C13—C12	112.5 (2)
O2—C4—C5	115.0 (2)	N2—C13—H13A	109.1
C3—C4—C5	121.0 (3)	C12—C13—H13A	109.1
C6—C5—C4	119.5 (2)	N2—C13—H13B	109.1
C6—C5—H5	120.2	C12—C13—H13B	109.1
C4—C5—H5	120.2	H13A—C13—H13B	107.8
C5—C6—C1	121.4 (3)	N3—C14—S1	178.8 (2)
C5—C6—H6	119.3	O2—C15—H15A	109.5
C1—C6—H6	119.3	O2—C15—H15B	109.5
N1—C7—C1	125.4 (2)	H15A—C15—H15B	109.5
N1—C7—H7	117.3	O2—C15—H15C	109.5
C1—C7—H7	117.3	H15A—C15—H15C	109.5
N1—C8—C9	105.9 (2)	H15B—C15—H15C	109.5
N1—C8—H8A	110.6

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.93	2.40	3.313 (4)	165
C7—H7···O2ii	0.93	2.44	3.329 (4)	160
C10—H10B···S1iii	0.97	2.87	3.797 (2)	161
C13—H13A···O1iv	0.97	2.49	3.432 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.93	2.40	3.313 (4)	165
C7—H7⋯O2ii	0.93	2.44	3.329 (4)	160
C10—H10B⋯S1iii	0.97	2.87	3.797 (2)	161
C13—H13A⋯O1iv	0.97	2.49	3.432 (3)	165

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .