Dichlorido{2-morpholino-N-[1-(2-pyrid­yl)ethyl­idene]ethanamine-κ3 N,N′,N′′}zinc(II)

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

doi:10.1107/S1600536810050671

. 2010 Dec 11;67(Pt 1):m55. doi: 10.1107/S1600536810050671

Dichlorido{2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³ N,N′,N′′}zinc(II)

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

PMCID: PMC3050202 PMID: 21522573

Abstract

In the title compound, [ZnCl₂(C₁₃H₁₉N₃O)], the Schiff base ligand acts as an N,N′,N′′-tridentate chelating agent, making two five-membered rings with the Zn^II ion. The metal atom is five-coordinated by the Schiff base ligand and two Cl atoms in a distorted square-pyramidal geometry. An intramolecular C—H⋯Cl interaction occurs. In the crystal, adjacent molecules are linked together via C—H⋯Cl hydrogen-bonding and long range C—H⋯O and C—H⋯Cl interactions into a three-dimensional network.

Related literature

For the crystal structure of an analogous Cd^II complex, see: Ikmal Hisham et al. (2010 ▶). For crystal structures of similar Zn^II complexes, see: Chattopadhyay et al. (2009 ▶); Sun (2005 ▶).

Experimental

Crystal data

[ZnCl₂(C₁₃H₁₉N₃O)]
M _r = 369.58
Monoclinic,
a = 9.5737 (12) Å
b = 13.7064 (17) Å
c = 12.0766 (15) Å
β = 106.643 (2)°
V = 1518.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.97 mm⁻¹
T = 100 K
0.35 × 0.21 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.546, T _max = 0.908
13693 measured reflections
2979 independent reflections
2552 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.091
S = 1.08
2979 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −0.39 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050671/pv2366sup1.cif

e-67-00m55-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050671/pv2366Isup2.hkl

e-67-00m55-Isup2.hkl^{(146.2KB, 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⋯Cl1ⁱ	0.95	2.71	3.625 (3)	161
C7—H7C⋯Cl2ⁱⁱ	0.98	2.77	3.619 (3)	146
C12—H12B⋯Cl1	0.99	2.73	3.526 (3)	138
C10—H10A⋯O1ⁱⁱⁱ	0.99	2.61	3.408 (3)	137
C9—H9B⋯Cl1^iv	0.99	2.88	3.665 (3)	137
C7—H7B⋯Cl1ⁱ	0.98	2.85	3.807 (3)	166
C8—H8A⋯Cl2^iv	0.99	2.87	3.750 (3)	149

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

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound is isostructural with the analogous Cd^II complex (Ikmal Hisham et al., 2010). The Schiff base, 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine and two Cl atoms coordinate the Zn^II ion in a distorted square-pyramidal geometry (τ = 0.22). The Zn—Cl and Zn—N bond lengths in the structure are in agreement with the values reported in the literature (Chattopadhyay et al., 2009; Sun, 2005). In the crystal structure, intermolecular C—H···Cl hydrogen bonding and long range C—H···O and C—H···Cl interactions link the adjacent molecules into a three-dimensional network. An intramolecular C—H···Cl hydrogen bonding has also been observed.

Experimental

A mixture of 2-acetylpyridine (0.20 g, 1.65 mmol) and 4-(2-aminoethyl)morpholine (0.21 g, 1.65 mmol) in the presence of a few drops of HCl (37%) in ethanol (20 ml) was refluxed. After 2 hr a solution of zinc(II) acetate dihydrate (0.36 g, 1.65 mmol) in a minimum amount of water was added and the resulting solution was refluxed for 30 min, then set aside at room temperature. The crystals of the title complex were obtained after a few days.