[(2-Morpholinoeth-yl)(2-pyridylmethyl-ene)amine]dithio-cyanato-zinc(II).

The title compound, [Zn(NCS)(2)(C(12)H(17)N(3)O)], was prepared by the reaction of zinc acetate with pyridine-2-carbaldehyde, 2-morpholinoethyl-amine and ammonium thio-cyanate in an ethanol solution. The Zn(II) atom is five coordinate with a distorted trigonal-bipyramidal geometry, coordinating with three N atoms of the Schiff base (2-morpholinoeth-yl)(2-pyridylmethyl-idene)amine and two N atoms from two thio-cyanate ligands. The morpholine ring adopts a chair configuration.

Related literature

For background literature on Schiff base complexes, see: Costes et al. (2002 ▶); Erxleben (2001 ▶); Lacroix et al. (1996 ▶); Odoko et al. (2006 ▶); Ali et al. (2006 ▶). For literature on related zinc(II) complexes, see: Li et al. (2008 ▶); Eltayeb et al. (2007 ▶); Ali et al. (2008 ▶); Zhang & Wang (2007 ▶).

Experimental

Crystal data

[Zn(NCS)2(C12H17N3O)]

M = 400.82

Triclinic,

a = 8.185 (2) Å

b = 8.654 (2) Å

c = 13.368 (4) Å

α = 98.439 (3)°

β = 102.587 (3)°

γ = 102.501 (3)°

V = 883.3 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.64 mm−1

T = 298 (2) K

0.23 × 0.23 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.705, T max = 0.736

7386 measured reflections

3770 independent reflections

2989 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.04

3770 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536808044061/su2087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808044061/su2087Isup2.hkl

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

[Zn(NCS)2(C12H17N3O)]	Z = 2
Mr = 400.82	F(000) = 412
Triclinic, P1	Dx = 1.507 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.185 (2) Å	Cell parameters from 2675 reflections
b = 8.654 (2) Å	θ = 2.4–25.0°
c = 13.368 (4) Å	µ = 1.64 mm−1
α = 98.439 (3)°	T = 298 K
β = 102.587 (3)°	Block, colorless
γ = 102.501 (3)°	0.23 × 0.23 × 0.20 mm
V = 883.3 (4) Å3

Bruker SMART 1000 CCD area-detector diffractometer	3770 independent reflections
Radiation source: fine-focus sealed tube	2989 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.705, Tmax = 0.736	k = −11→10
7386 measured reflections	l = −17→16

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.064P)2 + 0.1459P] where P = (Fo2 + 2Fc2)/3
3770 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.47 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
Zn1	0.87080 (4)	0.35121 (4)	0.23426 (3)	0.04844 (15)
S1	0.75132 (16)	0.05952 (14)	−0.10471 (7)	0.0759 (3)
S2	1.40376 (14)	0.73452 (15)	0.38080 (9)	0.0854 (4)
O1	1.1836 (4)	0.1269 (4)	0.4455 (2)	0.0791 (8)
N1	0.7747 (4)	0.5343 (3)	0.1472 (2)	0.0551 (7)
N2	0.6437 (3)	0.3649 (3)	0.2720 (2)	0.0552 (7)
N3	0.8546 (3)	0.1714 (3)	0.3427 (2)	0.0493 (6)
N4	0.8437 (4)	0.1978 (4)	0.1048 (2)	0.0662 (8)
N5	1.0969 (4)	0.5041 (4)	0.2956 (3)	0.0793 (10)
C1	0.6221 (4)	0.5515 (4)	0.1613 (3)	0.0531 (8)
C2	0.5377 (5)	0.6554 (4)	0.1166 (3)	0.0622 (9)
H2	0.4323	0.6652	0.1285	0.075*
C3	0.6133 (5)	0.7444 (4)	0.0539 (3)	0.0662 (10)
H3	0.5592	0.8155	0.0223	0.079*
C4	0.7674 (5)	0.7276 (4)	0.0385 (3)	0.0690 (10)
H4	0.8204	0.7867	−0.0038	0.083*
C5	0.8445 (5)	0.6212 (4)	0.0866 (3)	0.0648 (9)
H5	0.9503	0.6103	0.0759	0.078*
C6	0.5531 (4)	0.4478 (4)	0.2283 (3)	0.0603 (9)
H6	0.4434	0.4439	0.2382	0.072*
C7	0.5856 (5)	0.2577 (6)	0.3393 (3)	0.0776 (12)
H7A	0.4603	0.2194	0.3188	0.093*
H7B	0.6214	0.3151	0.4117	0.093*
C8	0.6656 (5)	0.1177 (5)	0.3275 (3)	0.0730 (11)
H8A	0.6415	0.0524	0.3782	0.088*
H8B	0.6134	0.0506	0.2581	0.088*
C9	0.9411 (5)	0.2391 (4)	0.4547 (3)	0.0612 (9)
H9A	0.8978	0.1647	0.4962	0.073*
H9B	0.9127	0.3402	0.4752	0.073*
C10	1.1332 (5)	0.2682 (5)	0.4768 (3)	0.0723 (11)
H10A	1.1776	0.3503	0.4404	0.087*
H10B	1.1840	0.3088	0.5513	0.087*
C11	1.1103 (5)	0.0677 (5)	0.3379 (3)	0.0757 (11)
H11A	1.1471	−0.0283	0.3162	0.091*
H11B	1.1522	0.1484	0.2998	0.091*
C12	0.9161 (5)	0.0269 (4)	0.3108 (3)	0.0639 (9)
H12A	0.8704	−0.0134	0.2360	0.077*
H12B	0.8735	−0.0576	0.3460	0.077*
C13	0.8047 (4)	0.1408 (4)	0.0181 (3)	0.0504 (7)
C14	1.2216 (5)	0.6003 (4)	0.3288 (3)	0.0560 (8)

	U11	U22	U33	U12	U13	U23
Zn1	0.0390 (2)	0.0533 (2)	0.0485 (2)	0.00680 (15)	0.01199 (15)	0.00305 (16)
S1	0.0891 (7)	0.0910 (7)	0.0462 (5)	0.0300 (6)	0.0125 (5)	0.0066 (5)
S2	0.0656 (6)	0.0863 (7)	0.0827 (7)	−0.0173 (5)	0.0278 (6)	−0.0084 (6)
O1	0.0664 (17)	0.090 (2)	0.0778 (19)	0.0235 (15)	0.0049 (14)	0.0222 (16)
N1	0.0487 (15)	0.0542 (16)	0.0604 (17)	0.0143 (12)	0.0129 (13)	0.0061 (13)
N2	0.0465 (15)	0.0640 (16)	0.0577 (17)	0.0151 (13)	0.0190 (13)	0.0100 (14)
N3	0.0469 (14)	0.0472 (14)	0.0473 (14)	0.0036 (11)	0.0098 (11)	0.0060 (11)
N4	0.083 (2)	0.0677 (19)	0.0506 (17)	0.0277 (16)	0.0191 (15)	0.0057 (15)
N5	0.0497 (17)	0.077 (2)	0.090 (3)	−0.0094 (16)	−0.0065 (17)	0.0269 (19)
C1	0.0496 (18)	0.0513 (18)	0.0517 (19)	0.0153 (14)	0.0064 (14)	−0.0036 (14)
C2	0.056 (2)	0.059 (2)	0.067 (2)	0.0235 (16)	0.0071 (17)	−0.0023 (17)
C3	0.072 (2)	0.0517 (19)	0.068 (2)	0.0210 (17)	0.0016 (19)	0.0079 (17)
C4	0.070 (2)	0.058 (2)	0.077 (3)	0.0139 (18)	0.017 (2)	0.0159 (19)
C5	0.055 (2)	0.063 (2)	0.080 (3)	0.0176 (17)	0.0196 (18)	0.0153 (19)
C6	0.0466 (18)	0.070 (2)	0.063 (2)	0.0184 (16)	0.0179 (16)	0.0011 (18)
C7	0.053 (2)	0.107 (3)	0.086 (3)	0.018 (2)	0.034 (2)	0.038 (2)
C8	0.051 (2)	0.078 (3)	0.084 (3)	−0.0047 (18)	0.0138 (19)	0.031 (2)
C9	0.074 (2)	0.0553 (19)	0.0471 (19)	0.0103 (17)	0.0135 (17)	0.0017 (15)
C10	0.071 (2)	0.070 (2)	0.057 (2)	0.0043 (19)	−0.0076 (18)	0.0106 (18)
C11	0.075 (3)	0.085 (3)	0.081 (3)	0.035 (2)	0.031 (2)	0.022 (2)
C12	0.082 (3)	0.0477 (18)	0.055 (2)	0.0115 (17)	0.0100 (18)	0.0070 (16)
C13	0.0516 (18)	0.0499 (17)	0.057 (2)	0.0198 (14)	0.0182 (15)	0.0183 (16)
C14	0.061 (2)	0.064 (2)	0.0527 (19)	0.0207 (17)	0.0245 (17)	0.0200 (16)

Zn1—N5	1.951 (3)	C3—C4	1.356 (6)
Zn1—N4	1.959 (3)	C3—H3	0.9300
Zn1—N2	2.051 (3)	C4—C5	1.381 (5)
Zn1—N1	2.273 (3)	C4—H4	0.9300
Zn1—N3	2.279 (3)	C5—H5	0.9300
S1—C13	1.611 (4)	C6—H6	0.9300
S2—C14	1.618 (4)	C7—C8	1.501 (6)
O1—C11	1.401 (5)	C7—H7A	0.9700
O1—C10	1.409 (5)	C7—H7B	0.9700
N1—C5	1.319 (5)	C8—H8A	0.9700
N1—C1	1.339 (4)	C8—H8B	0.9700
N2—C6	1.253 (4)	C9—C10	1.492 (5)
N2—C7	1.462 (5)	C9—H9A	0.9700
N3—C8	1.475 (4)	C9—H9B	0.9700
N3—C9	1.479 (4)	C10—H10A	0.9700
N3—C12	1.486 (4)	C10—H10B	0.9700
N4—C13	1.137 (4)	C11—C12	1.500 (6)
N5—C14	1.122 (4)	C11—H11A	0.9700
C1—C2	1.375 (5)	C11—H11B	0.9700
C1—C6	1.471 (5)	C12—H12A	0.9700
C2—C3	1.374 (6)	C12—H12B	0.9700
C2—H2	0.9300
N5—Zn1—N4	117.35 (16)	N2—C6—H6	120.4
N5—Zn1—N2	126.27 (15)	C1—C6—H6	120.4
N4—Zn1—N2	114.94 (12)	N2—C7—C8	107.8 (3)
N5—Zn1—N1	91.02 (12)	N2—C7—H7A	110.1
N4—Zn1—N1	93.10 (12)	C8—C7—H7A	110.1
N2—Zn1—N1	74.60 (11)	N2—C7—H7B	110.1
N5—Zn1—N3	104.43 (12)	C8—C7—H7B	110.1
N4—Zn1—N3	97.98 (11)	H7A—C7—H7B	108.5
N2—Zn1—N3	79.39 (11)	N3—C8—C7	112.0 (3)
N1—Zn1—N3	153.98 (10)	N3—C8—H8A	109.2
C11—O1—C10	109.3 (3)	C7—C8—H8A	109.2
C5—N1—C1	117.5 (3)	N3—C8—H8B	109.2
C5—N1—Zn1	130.3 (2)	C7—C8—H8B	109.2
C1—N1—Zn1	112.2 (2)	H8A—C8—H8B	107.9
C6—N2—C7	123.2 (3)	N3—C9—C10	112.0 (3)
C6—N2—Zn1	119.9 (2)	N3—C9—H9A	109.2
C7—N2—Zn1	116.5 (2)	C10—C9—H9A	109.2
C8—N3—C9	110.1 (3)	N3—C9—H9B	109.2
C8—N3—C12	107.7 (3)	C10—C9—H9B	109.2
C9—N3—C12	107.8 (3)	H9A—C9—H9B	107.9
C8—N3—Zn1	100.9 (2)	O1—C10—C9	112.2 (3)
C9—N3—Zn1	115.6 (2)	O1—C10—H10A	109.2
C12—N3—Zn1	114.3 (2)	C9—C10—H10A	109.2
C13—N4—Zn1	159.8 (3)	O1—C10—H10B	109.2
C14—N5—Zn1	175.1 (3)	C9—C10—H10B	109.2
N1—C1—C2	123.0 (3)	H10A—C10—H10B	107.9
N1—C1—C6	113.7 (3)	O1—C11—C12	111.9 (3)
C2—C1—C6	123.3 (3)	O1—C11—H11A	109.2
C3—C2—C1	118.2 (3)	C12—C11—H11A	109.2
C3—C2—H2	120.9	O1—C11—H11B	109.2
C1—C2—H2	120.9	C12—C11—H11B	109.2
C4—C3—C2	119.4 (3)	H11A—C11—H11B	107.9
C4—C3—H3	120.3	N3—C12—C11	110.8 (3)
C2—C3—H3	120.3	N3—C12—H12A	109.5
C3—C4—C5	118.9 (4)	C11—C12—H12A	109.5
C3—C4—H4	120.6	N3—C12—H12B	109.5
C5—C4—H4	120.6	C11—C12—H12B	109.5
N1—C5—C4	123.0 (4)	H12A—C12—H12B	108.1
N1—C5—H5	118.5	N4—C13—S1	179.4 (3)
C4—C5—H5	118.5	N5—C14—S2	177.4 (3)
N2—C6—C1	119.3 (3)