{2-Morpholino-N-[1-(2-pyrid­yl)ethyl­idene]ethanamine-κ3 N,N′,N′′}bis­(thio­cyanato-κN)copper(II)

Nura Suleiman Gwaram; Nurul Azimah Ikmal Hisham; Hamid Khaledi; Hapipah Mohd Ali

doi:10.1107/S1600536810050889

. 2010 Dec 11;67(Pt 1):m58. doi: 10.1107/S1600536810050889

{2-Morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³ N,N′,N′′}bis(thiocyanato-κN)copper(II)

Nura Suleiman Gwaram ^a, Nurul Azimah Ikmal Hisham ^a, Hamid Khaledi ^a,^*, Hapipah Mohd Ali ^a

PMCID: PMC3050323 PMID: 21522576

Abstract

In the title compound, [Cu(NCS)₂(C₁₃H₁₉N₃O)], the Cu^II ion is five-coordinated by the N,N′,N′′-tridentate Schiff base and the N atoms of two isothiocyanate ligands in a square-pyramidal geometry. In the crystal, C—H⋯N, C—H⋯O and C—H⋯S interactions link adjacent molecules into layers parallel to the ac plane. A weak intermolecular π–π interaction occurs between the aromatic rings with a centroid–centroid distance of 3.9412 (9) Å.

Related literature

For related structures of Cu(II) complexes, see: Drew et al. (2009 ▶); You et al. (2006 ▶); Yue et al. (2005 ▶).

Experimental

Crystal data

[Cu(NCS)₂(C₁₃H₁₉N₃O)]
M _r = 413.01
Monoclinic,
a = 10.6912 (1) Å
b = 14.0350 (2) Å
c = 12.2530 (2) Å
β = 92.203 (1)°
V = 1837.22 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.43 mm⁻¹
T = 100 K
0.41 × 0.39 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.592, T _max = 0.894
16491 measured reflections
4007 independent reflections
3593 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.023
wR(F ²) = 0.061
S = 1.08
4007 reflections
218 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050889/is2639sup1.cif

e-67-00m58-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050889/is2639Isup2.hkl

e-67-00m58-Isup2.hkl^{(196.4KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	0.95	2.40	3.211 (2)	144
C7—H7B⋯O1ⁱ	0.98	2.33	3.248 (2)	155
C7—H7C⋯S2ⁱⁱ	0.98	2.83	3.7021 (18)	149
C8—H8B⋯N5ⁱⁱ	0.99	2.55	3.367 (2)	140
C13—H13A⋯N4	0.99	2.58	3.181 (2)	119

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the University of Malaya for funding this study (UMRG grant RG024/09BIO).

supplementary crystallographic information

Comment

The title compound is a mixed-ligand copper(II) complex with isothiocyanate and the Schiff base 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine. The geometry of the complex is slightly distorted square-pyramidal (τ = 0.05) with the N,N',N"-tridentate Schiff base and one SCN ligand at the basal positions, while the apical position is occupied by a second SCN ligand. This arrangement has been observed in some other mixed-ligand copper(II) complexes (Drew et al., 2009; You et al., 2006; Yue et al., 2005). In the crystal structure, the C—H···N, C—H···O and C—H···S interactions within the range for normal hydrogen bonds link the adjacent molecules into layers parallel to the ac plane (Fig. 2). An intramolecular C—H···N hydrogen bonding is also observed. Moreover, the aromatic rings of each two molecules related by the symmetry -x + 2, -y, -z + 1, are arranged in an antiparallel manner with centroid-centroid separation of 3.9412 (9) Å, indicative of a weak π–π interaction.

Experimental

A mixture of 2-acetylpyridine (0.20 g, 1.65 mmol) and 4-(2-aminoethyl)morpholine (0.21 g, 1.65 mmol) in ethanol (20 ml) was refluxed for 2 hr followed by addition of a solution of copper(II) acetate monohydrate (0.33 g, 1.65 mmol) and sodium thiocyanete (0.134 g, 1.65 mmol) in a minimum amount of ethanol. The resulting solution was refluxed for 30 min, then left at room temperature. The crystals of the title complex were obtained in a week.