Dibromido{2-(morpholin-4-yl)-N-[1-(2-pyrid­yl)ethyl­idene]ethanamine-κ3 N,N′,N′′}cadmium

Nura Suleiman Gwaram; Hamid Khaledi; Hapipah Mohd Ali

doi:10.1107/S160053681100554X

. 2011 Feb 19;67(Pt 3):m347. doi: 10.1107/S160053681100554X

Dibromido{2-(morpholin-4-yl)-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³ N,N′,N′′}cadmium

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

PMCID: PMC3052017 PMID: 21522276

Abstract

The Cd^II ion in the title compound, [CdBr₂(C₁₃H₁₉N₃O)], is five-coordinated by the N,N′,N′′-tridentate Schiff base ligand and two Br atoms in a distorted square-pyramidal geometry. In the crystal, intermolecular C—H⋯O and C—H⋯Br hydrogen bonds link adjacent molecules into layers parallel to the ab plane. An intramolecular C—H⋯Br interaction is also observed.

Related literature

For the crystal structure of the analogous CdCl₂ complex, see: Ikmal Hisham et al. (2010 ▶). For the crystal structures of similar CdBr₂ complexes, see: Bermejo et al. (1999 ▶, 2003 ▶). For a description of the geometry of complexes with five-coordinate metal atoms, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[CdBr₂(C₁₃H₁₉N₃O)]
M _r = 505.53
Orthorhombic,
a = 9.1906 (8) Å
b = 12.2604 (10) Å
c = 14.7499 (12) Å
V = 1662.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 6.12 mm⁻¹
T = 100 K
0.33 × 0.27 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.237, T _max = 0.389
20236 measured reflections
3642 independent reflections
3445 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.021
wR(F ²) = 0.041
S = 1.09
3642 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.54 e Å⁻³
Absolute structure: Flack (1983 ▶), 1556 Friedel pairs
Flack parameter: 0.023 (9)

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/S160053681100554X/bg2390sup1.cif

e-67-0m347-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100554X/bg2390Isup2.hkl

e-67-0m347-Isup2.hkl^{(178.6KB, 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
C3—H3⋯O1ⁱ	0.95	2.42	3.132 (4)	131
C7—H7B⋯Br1ⁱⁱ	0.98	2.92	3.840 (4)	157
C10—H10A⋯O1ⁱⁱⁱ	0.99	2.45	3.383 (4)	156
C11—H11B⋯Br2	0.99	2.91	3.727 (4)	141

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

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound was obtained upon the reaction of 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine with Cd^II ion in the presence of potassium bromide. Similar to the structure of the analogous CdCl₂ complex (Ikmal Hisham et al., 2010), the metal center is five-coordinated by the N,N',N"-tridentate Schiff base ligand and two halogen atoms. The geometry of the complexes can be determined by using the index τ = (β-α)/60, where β is the largest angle and α is the second one around the metal center. For an ideal square-pyramid τ is 0, while it is 1 in a perfect trigonal-bipyramid (Addison et al.,1984). The τ value in the present structure is calculated to be 0.18, indicative of a distorted square-pyramidal geometry. The Cd—Br bond lengths in the complex are in agreement with the values reported in the literature (Bermejo et al., 1999; Bermejo et al., 2003). In the crystal, the adjacent molecules are connected together via C—H···O and C—H···Br hydrogen bonds, forming infinite layers parallel to the ab plane. Moreover an intramolecluar C—H···Br occurs.

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 cadmium(II) acetate dihydrate (0.44 g, 1.65 mmol) and potassium bromide (0.196 g, 1.65 mmol) in a minimum amount of water was added. The resulting solution was refluxed for 30 min, and then left at room temperature. The crystals of the title complex were obtained in a few days.