Dichlorido{2-(morpholin-4-yl)-N-[1-(pyridin-2-yl)ethyl­idene]ethanamine-κ3 N,N′,N′′}copper(II) monohydrate

Nura Suleiman Gwaram; Hamid Khaledi; Hapipah Mohd Ali

doi:10.1107/S1600536811004892

. 2011 Feb 12;67(Pt 3):m334. doi: 10.1107/S1600536811004892

Dichlorido{2-(morpholin-4-yl)-N-[1-(pyridin-2-yl)ethylidene]ethanamine-κ³ N,N′,N′′}copper(II) monohydrate

Nura Suleiman Gwaram ^a, Hamid Khaledi ^a,^*, Hapipah Mohd Ali ^a

PMCID: PMC3052153 PMID: 21522265

Abstract

In the title compound, [CuCl₂(C₁₃H₁₉N₃O)]·H₂O, the tridentate Schiff base ligand and the two Cl atoms complete a distorted square-pyramidal coordination geometry around the Cu^II ion in which the three N atoms and one Cl atom are located in the basal plane and the other Cl atom is at the apical position. In the crystal, O—H⋯Cl hydrogen bonds link the complex molecules and the uncoordinated water molecules into infinite chains along the a axis. The chains are further connected into a three-dimensional network via C—H⋯O and C—H⋯Cl interactions.

Related literature

For the structures of CuCl₂ complexes with similar ligands, see: Saleh Salga et al. (2010 ▶); Wang et al. (2009 ▶). For the structure of a CdCl₂ complex with the same Schiff base ligand, see: Ikmal Hisham et al. (2010 ▶). For a description of the geometry of complexes with a five-coordinate metal atom, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[CuCl₂(C₁₃H₁₉N₃O)]·H₂O
M _r = 385.77
Monoclinic,
a = 7.9194 (8) Å
b = 8.5793 (8) Å
c = 22.925 (2) Å
β = 91.981 (1)°
V = 1556.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.75 mm⁻¹
T = 100 K
0.18 × 0.16 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.743, T _max = 0.858
9634 measured reflections
3348 independent reflections
2948 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.025
wR(F ²) = 0.060
S = 1.05
3348 reflections
197 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.34 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/S1600536811004892/is2674sup1.cif

e-67-0m334-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004892/is2674Isup2.hkl

e-67-0m334-Isup2.hkl^{(164.2KB, 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
O2—H2A⋯Cl2ⁱ	0.84 (2)	2.35 (2)	3.1829 (16)	173 (2)
O2—H2B⋯Cl1	0.83 (2)	2.48 (2)	3.2841 (18)	164 (2)
C2—H2⋯O2ⁱⁱ	0.95	2.41	3.307 (2)	156
C3—H3⋯Cl2ⁱⁱⁱ	0.95	2.82	3.619 (2)	142
C4—H4⋯O2^iv	0.95	2.50	3.445 (2)	172
C7—H7A⋯Cl1^v	0.98	2.68	3.6179 (19)	161
C8—H8A⋯O1^vi	0.99	2.47	3.336 (2)	146
C10—H10B⋯Cl1	0.99	2.79	3.4496 (19)	124
C10—H10A⋯Cl2	0.99	2.71	3.3566 (19)	123

Open in a new tab

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

Acknowledgments

The authors thank University of Malaya for funding this study (FRGS grant No. FP004/2010B).

supplementary crystallographic information

Comment

The asymmetric unit of the title compound consists of a copper(II) complex and one molecule of water. Like the CdCl₂ complex of the Schiff base, 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine, (Ikmal Hisham et al., 2010) the metal ion in the present structure is five-coordinated by the N,N',N"-tridentate Schiff base ligand and two Cl atoms in a distorted square-pyramidal geometry, the τ value (Addison et al.,1984) being 0.15. The Cu—Cl and Cu—N interatomic distances are comparable to the values reported in the literature (Saleh Salga et al., 2010; Wang et al., 2009). In the crystal, the adjacent metal complexes and water molecules are linked into a three-dimensional network via O—H···Cl, C—H···Cl and C—H···O interactions. In addition, intramolecular C—H···Cl hydrogen bonding is 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 ethanol (20 ml) was refluxed. After 2 hr a solution of copper(II) chloride dihydrate (0.28 g, 1.65 mmol) in a minimum amount of ethanol 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.