Dibromido[(1R,2R,N 1 S)-N-(pyridin-2-ylmeth­yl)cyclo­hexane-1,2-diamine-κ3 N,N′,N′′]cadmium

Run-Ting Yin; Zhe Cao; Lin Cheng

doi:10.1107/S1600536811007033

. 2011 Mar 2;67(Pt 4):m392. doi: 10.1107/S1600536811007033

Dibromido[(1R,2R,N ¹ S)-N-(pyridin-2-ylmethyl)cyclohexane-1,2-diamine-κ³ N,N′,N′′]cadmium

Run-Ting Yin ^a, Zhe Cao ^a, Lin Cheng ^a,^*

PMCID: PMC3099840 PMID: 21753928

Abstract

In the title compound, [CdBr₂(C₁₂H₁₉N₃)], the Cd^II atom is coordinated by the three N atoms of the (1R,2R)-N-(pyridin-2-ylmethyl)cyclohexane-1,2-diamine ligand and a bromide ion in the basal plane, and by a second bromide in the apical position. The coordination environment can be described as distorted square pyramidal. The coordination of the enantiopure ligand to the metal atom renders the central N atom chiral with an S configuration, so the complex is enantiomerically pure and corresponds to the S,R,R diastereoisomer. In the crystal, the molecules are linked via weak N—H⋯Br hydrogen bonds into a chain parallel to the b axis.

Related literature

For related structures, see: Gou et al. (2010 ▶). For non-linear optical properties of chiral coordination polymers, see: He et al. (2010 ▶).

Experimental

Crystal data

[CdBr₂(C₁₂H₁₉N₃)]
M _r = 477.52
Orthorhombic,
a = 8.7153 (16) Å
b = 9.1978 (17) Å
c = 19.759 (4) Å
V = 1583.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 6.41 mm⁻¹
T = 173 K
0.12 × 0.09 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T _min = 0.513, T _max = 0.628
9389 measured reflections
3048 independent reflections
2348 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.052
S = 0.96
3048 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.48 e Å⁻³
Absolute structure: Flack (1983 ▶), 1244 Friedel pairs
Flack parameter: 0.049 (11)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811007033/dn2658sup1.cif

e-67-0m392-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007033/dn2658Isup2.hkl

e-67-0m392-Isup2.hkl^{(149.6KB, 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
N3—H3B⋯Br2ⁱ	0.92	2.89	3.750 (5)	156
N3—H3C⋯Br1ⁱⁱ	0.92	2.59	3.498 (5)	168

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

Acknowledgments

The authors thank the Program for Young Excellent Talents in Southeast University for financial support.

supplementary crystallographic information

Comment

Recently, rational design and synthesis of chiral coordination polymers have been of great interests due to their potential utility in enantiomerically selective catalysis and separations, second-order nonlinearoptical (NLO) applications and luminescence (He et al., 2010). A simple and effective design route for such polymers is to appropriately organize the metal ions into ordered architectures by use of chiral ligands. Herein, we report a new chiral complex, Zn(pcd)Br₂ (pcd = (1R,2R)-N¹-(pyridin-2-ylmethyl)cyclohexane -1,2-diamine), with a enantiomerically pure pcd ligand.

The title compound is a mononuclear complex, in which the coordination environment of Cd^II ion can be described as distorted square-pyramidal, being surrounded by one tridentate ligand and two bromine anions (Fig. 1).

The molecules are linked to each other, via weak N—H···Br hydrogen bonds, into a one-dimensional hydrogen bonding network developping parallel to the b axis (Table 1, Fig. 2).

Experimental

(1R,2R)-N¹-(pyridin-2-ylmethyl)cyclohexane -1,2-diamine (0.041 g, 0.2 mmol) dissolved in water (8 ml) was added to a methanol solution (10 ml) of CdBr₂ (0.054 g, 0.2 mmol). The mixture solution was stirred for 1 h at room temperature and then filtered. The filtrate was allowed to evaporate slowly at room temperature. After 2 weeks, yellow block crystals were obtained in 32.5% yield (0.031 g).