{5-Meth­oxy-2-[(2-morpholinoethyl)­iminometh­yl]phenolato}(thio­cyanato-κN)­nickel(II)

Liu, L.

doi:10.1107/S160053681000468X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m289

doi:10.1107/S160053681000468X

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{5-Methoxy-2-[(2-morpholinoethyl)iminomethyl]phenolato}(thiocyanato-κN)nickel(II)

Lin Liu ^a ^*

^aCollege of Chemistry and Biology Engineering, Yichun University, Yichun 336000, People's Republic of China
^*Correspondence e-mail: liulin_ycu@126.com

(Received 28 January 2010; accepted 5 February 2010; online 13 February 2010)

In the mononuclear title complex, [Ni(C₁₄H₁₉N₂O₃)(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 thiocyanate ligand. The crystal structure is stabilized by intermolecular C—H⋯S and C—H⋯O hydrogen bonds, forming a three-dimensional network.

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 related structures, see: Liu (2010 ); Montazerozohori et al. (2009 ); Zhu et al. (2004 , 2006 ).

Experimental

Crystal data

[Ni(C₁₄H₁₉N₂O₃)(NCS)]
M_r = 380.10
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.090
S = 1.03
3554 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.38 e Å⁻³

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⋯O1^iv	0.97	2.49	3.432 (3)	165
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000468X/rz2416sup1.cif

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

checkCIF report

Comment top

Nickel(II) complexes with Schiff bases have been extensively studied (Campbell & Urbach, 1973; Wallis & Cummings, 1974; Polt et al., 2003; Mukhopadhyay et al., 2003). Recently, the author reported a nickel(II) complex with the Schiff base 2-[2-(ethylamino)ethyliminomethyl]-5-methoxyphenol (Liu, 2010). In this paper, the crystal structure of the title new nickel(II) complex, with the Schiff base 5-methoxy-2-[(2-morpholin-4-ylethylimino)methyl]phenol, is reported.

The Ni atom in the title complex is four-coordinate by the phenolate O atom, imine N atom, and amine N atom of the Schiff base ligand, and by the N atom of a thiocyanate ligand, forming a square-planar geometry (Fig. 1). The bond lengths and angles involving the metal atom are comparable with those observed in similar complexes (Montazerozohori et al., 2009; Zhu et al., 2004; Zhu et al., 2006). In the crystal structure, the complex molecules are linked into a three-dimensional network by intermolecular C—H···S and C—H···O hydrogen bonds (Table 1).

Related literature top

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 related structures, see: Liu (2010); Montazerozohori et al. (2009); Zhu et al. (2004, 2006).

Experimental top

Equimolar quantities (0.1 mmol) of 4-methoxysalicylaldehyde, N-(2-aminoethyl)morpholine, ammonium thiocyanate, and Ni(CH₃COO)₂.4H₂O were mixed and stirred in a methanol solution for 30 min at reflux. After keeping the filtrate in air for a few days, red block crystals suitable for X-ray analysis were formed.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title complex, with displacement ellipsoids drawn at the 30% probability level.

{5-Methoxy-2-[(2-morpholinoethyl)iminomethyl]phenolato}(thiocyanato-κN)nickel(II) top

Crystal data top

[Ni(C₁₄H₁₉N₂O₃)(NCS)]	F(000) = 792
M_r = 380.10	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	3554 independent reflections
Radiation source: fine-focus sealed tube	2729 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scan	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.777, T_max = 0.796	k = −7→15
9279 measured reflections	l = −15→15

Refinement top

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(F_o²) + (0.0433P)² + 0.1781P] where P = (F_o² + 2F_c²)/3
3554 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Ni(C₁₄H₁₉N₂O₃)(NCS)]	V = 1635.8 (4) Å³
M_r = 380.10	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3983 (18) Å	µ = 1.33 mm⁻¹
b = 11.8202 (17) Å	T = 298 K
c = 12.2913 (18) Å	0.20 × 0.20 × 0.18 mm
β = 114.756 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3554 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2729 reflections with I > 2σ(I)
T_min = 0.777, T_max = 0.796	R_int = 0.033
9279 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.03	Δρ_max = 0.35 e Å⁻³
3554 reflections	Δρ_min = −0.38 e Å⁻³
209 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.97	2.49	3.432 (3)	165

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₁₉N₂O₃)(NCS)]
M_r	380.10
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.3983 (18), 11.8202 (17), 12.2913 (18)
β (°)	114.756 (2)
V (Å³)	1635.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.33
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.777, 0.796
No. of measured, independent and observed [I > 2σ(I)] reflections	9279, 3554, 2729
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.090, 1.03
No. of reflections	3554
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.38

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.97	2.49	3.432 (3)	165

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, −y+1, −z.

Acknowledgements

This work was supported by Yichun University.

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Volume 66| Part 3| March 2010| Page m289

doi:10.1107/S160053681000468X

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{5-Meth­­oxy-2-[(2-morpholino­ethyl)­iminometh­yl]phenolato}(thio­cyanato-κN)­nickel(II)

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Experimental

Crystal data

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Refinement

Supporting information

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References

metal-organic compounds

{5-Methoxy-2-[(2-morpholinoethyl)iminomethyl]phenolato}(thiocyanato-κN)nickel(II)