Dibromido[(S)-2-(pyrrolidin-2-yl)-1H-benzimidazole]zinc(II)

Wei Dai; Da-Wei Fu

doi:10.1107/S1600536808019168

. 2008 Jul 9;64(Pt 8):m1016. doi: 10.1107/S1600536808019168

Dibromido[(S)-2-(pyrrolidin-2-yl)-1H-benzimidazole]zinc(II)

Wei Dai ^a, Da-Wei Fu ^a,^*

PMCID: PMC2961939 PMID: 21203009

Abstract

The title compound, [ZnBr₂(C₁₁H₁₃N₃)], was synthesized by hydrothermal reaction of ZnBr₂ and (S)-2-(pyrrolidin-2-yl)-1H-benzimidazole. The Zn^II atom has a distorted tetrahedral geometry and is coordinated by two N atoms from the chelating organic ligand and two terminal Br⁻ anions. In the crystal structure, molecules are linked into a chain along the [101] direction by N—H⋯Br and C—H⋯Br hydrogen bonds.

Related literature

For physical properties such as fluorescence and dielectric behaviors of metal-organic coordination compounds, see: Aminabhavi et al. (1986 ▶); Ye et al. (2008 ▶); Fu et al. (2007 ▶).

Experimental

Crystal data

[ZnBr₂(C₁₁H₁₃N₃)]
M _r = 412.43
Monoclinic,
a = 8.953 (3) Å
b = 11.668 (2) Å
c = 13.318 (2) Å
β = 91.443 (3)°
V = 1390.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 7.49 mm⁻¹
T = 298 (2) K
0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.459, T _max = 0.982 (expected range = 0.152–0.325)
13896 measured reflections
3179 independent reflections
2426 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.114
S = 0.99
3179 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −1.00 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019168/ci2621sup1.cif

e-64-m1016-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019168/ci2621Isup2.hkl

e-64-m1016-Isup2.hkl^{(156KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Br1—Zn1	2.3642 (8)
Zn1—N2	2.011 (3)
Zn1—N1	2.075 (4)
Zn1—Br2	2.3319 (7)

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N2—Zn1—N1	82.35 (14)
N2—Zn1—Br2	112.70 (10)
N1—Zn1—Br2	117.89 (10)
N2—Zn1—Br1	118.99 (11)
N1—Zn1—Br1	110.08 (11)
Br2—Zn1—Br1	112.03 (3)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3C⋯Br1ⁱ	0.86	2.74	3.516 (4)	150
C4—H4A⋯Br1ⁱⁱ	0.98	2.86	3.637 (5)	137
C1—H1A⋯Cg1ⁱⁱⁱ	0.97	2.78	3.673 (6)	153

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the centroid of the C6–C11 ring.

Acknowledgments

This work was supported by a Start-up Grant from Southeast University to Professor Ren-Gen Xiong, and a Excellent Doctoral Degree Foundation Grant from Southeast University to DWF.

supplementary crystallographic information

Comment

Metal-organic coordination compounds provide a class of complexes displaying interesting chemical and physical properties such as fluorescence and dielectric behaviors (Aminabhavi et al., 1986; Ye et al., 2008; Fu et al., 2007). There has been very strong interest in employing crystal-engineering strategies to generate desirable materials by the hydrothermal reaction. Here we report the synthesis and crystal structure of the title compound.

The Zn^II atom has a distorted tetrahedral geometry (Table 1) and is coordinated by two N atoms from the chelating S-2-(pyrrolidin-2-yl)-1H-benzimidazole ligand and two terminal Br^- anions (Fig. 1).

In the crystal structure, N—H···Br and C—H···Br hydrogen bonds (Table 2) link the molecules into a chain along [1 0 1] (Fig.2).

Experimental

The homochiral ligand S-2-(pyrrolidin-2-yl)-1H-benzimidazole was synthesized by reaction of S-pyrrolidine-2-carboxylic acid and benzene-1,2-diamine according to the procedure described in the literature (Aminabhavi et al., 1986). A mixture of S-2-(pyrrolidin-2-yl)-1H-benzimidazole (18.7 mg, 0.1 mmol), ZnBr₂ (33.9 mg, 0.1 mmol) and water (1 ml) sealed in a glass tube was maintained at 343 K. Crystals suitable for X-ray ananlysis were obtained after 3 d.