Dichlorido(2-{[3-(morpholin-4-ium-4-yl)prop­yl]imino­meth­yl}phenolate)zinc

Nurul Azimah Ikmal Hisham; Hamid Khaledi; Hapipah Mohd Ali

doi:10.1107/S1600536811022021

. 2011 Jun 18;67(Pt 7):m932. doi: 10.1107/S1600536811022021

Dichlorido(2-{[3-(morpholin-4-ium-4-yl)propyl]iminomethyl}phenolate)zinc

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

PMCID: PMC3151802 PMID: 21836916

Abstract

In the zwitterionic zinc title complex, [ZnCl₂(C₁₄H₂₀N₂O₂)], the Zn^II ion is four-coordinated in a distorted tetrahedral geometry. The Schiff base ligand employs its phenolate O and imine N atoms to coordinate the metal atom in a bidentate mode. Two Cl atoms complete the tetrahedral coordination environment. In the crystal, a pair of N—H⋯O hydrogen bonds connect the molecules into a centrosymmetric dimer. C—H⋯O, C—H⋯Cl and C—H⋯π interactions are also observed.

Related literature

For related structures of similar zwitterionic ZnCl₂ complexes, see: Qiu (2006 ▶); Ye & You (2008 ▶); Zhu (2008 ▶).

Experimental

Crystal data

[ZnCl₂(C₁₄H₂₀N₂O₂)]
M _r = 384.59
Monoclinic,
a = 8.11276 (10) Å
b = 11.21021 (13) Å
c = 18.4097 (2) Å
β = 92.0168 (6)°
V = 1673.24 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.79 mm⁻¹
T = 100 K
0.37 × 0.32 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.557, T _max = 0.663
14420 measured reflections
3824 independent reflections
3557 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.020
wR(F ²) = 0.051
S = 1.07
3824 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.33 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 datablock(s) I, global. DOI: 10.1107/S1600536811022021/is2701sup1.cif

e-67-0m932-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022021/is2701Isup2.hkl

e-67-0m932-Isup2.hkl^{(187.5KB, hkl)}

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1ⁱ	0.90 (1)	1.81 (1)	2.6954 (14)	170 (2)
C5—H5⋯O2ⁱⁱ	0.95	2.39	3.2161 (16)	146
C9—H9A⋯Cl1ⁱⁱⁱ	0.99	2.83	3.6732 (13)	144
C10—H10A⋯Cl1ⁱ	0.99	2.82	3.6905 (13)	147
C14—H14A⋯Cl2ⁱⁱⁱ	0.99	2.69	3.5486 (13)	146
C14—H14B⋯Cl2^iv	0.99	2.78	3.6890 (14)	153
C12—H12B⋯Cg1^v	0.99	2.57	3.4366 (2)	146

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

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound was obtained via the complexation of ZnCl₂ with the in situ prepared Schiff base. The Schiff base ligand coordinates the metal ion via its phenolate oxygen and imine nitrogen atoms. The morpholine ring N atom stays away from the coordination and is protonated, implying the zwitterionic nature of the molecule. The tetrahedral geometry around the zinc(II) ion is completed by two Cl atoms. The coordination bond lengths in the complex are comparable to the corresponding values in similar structures (Qiu, 2006; Ye & You, 2008; Zhu, 2008). In the crystal, N—H···O hydrogen bonding connects pairs of the molecules into centrosymmetric dimers. The dimers are linked through C—H···O, C—H···Cl and C—H···π interactions into a three-dimensional network.

Experimental

A mixture of salicylaldehyde (0.20 g, 1.64 mmol) and N-(3-aminopropyl)morpholine (0.24 g, 1.64 mmol) in ethanol (20 ml) was refluxed for 2 hr followed by addition of a solution of zinc(II) chloride (0.22 g, 1.64 mmol) in a minimum amount of water. The resulting solution was refluxed for 30 min, then the solvent was removed under reduced pressure. The impure product was recrystallized from methanol to give the yellow crystals of the title compound.