Bis[2-(1H-1,2,3-benzotriazol-1-yl)acetic acid-κN 3]dichloridozinc(II)

Tian Hang; Qiong Ye

doi:10.1107/S1600536808006399

. 2008 May 3;64(Pt 6):m758. doi: 10.1107/S1600536808006399

Bis[2-(1H-1,2,3-benzotriazol-1-yl)acetic acid-κN ³]dichloridozinc(II)

Tian Hang ^a, Qiong Ye ^a,^*

PMCID: PMC2961613 PMID: 21202451

Abstract

In the title complex, [ZnCl₂(C₈H₇N₃O₂)₂], the Zn^II atom is coordinated by two chloride ions and two N atoms in a distorted tetrahedral coordination environment. In the crystal structure, molecules are linked by intermolecular C—H⋯O and O—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For synthesis of the organic ligand, see: Danan et al. (1997 ▶); Xu & Ye (2007 ▶).

Experimental

Crystal data

[ZnCl₂(C₈H₇N₃O₂)₂]
M _r = 490.60
Triclinic,
a = 8.0896 (16) Å
b = 9.6898 (19) Å
c = 12.703 (3) Å
α = 87.48 (3)°
β = 84.25 (3)°
γ = 83.95 (3)°
V = 984.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.55 mm⁻¹
T = 293 (2) K
0.3 × 0.2 × 0.1 mm

Data collection

Rigaku Mercury2 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.720, T _max = 0.860
10222 measured reflections
4512 independent reflections
4022 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.099
S = 1.09
4512 reflections
275 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.54 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006399/pk2083sup1.cif

e-64-0m758-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006399/pk2083Isup2.hkl

e-64-0m758-Isup2.hkl^{(221KB, 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
O1—H1C⋯O4ⁱ	0.82	2.20	3.015 (4)	171
O2—H2B⋯Cl1ⁱⁱ	0.93	2.59	3.348 (3)	139
C6—H6A⋯O4ⁱⁱⁱ	0.97	2.69	3.586 (4)	153

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

Acknowledgments

This work was supported by a Start-up Grant from Southeast University (to QY).

supplementary crystallographic information

Comment

Recently, we reported the structure of 2-(1H-benzo[d][1,2,3] triazol-1-yl)acetonitrile (Xu et al. (2007)). The reaction of it with ZnCl₂ in ethanol-water solution gives the title complex. The zinc(II) center is coordinated by two nitrogen atoms from the benzotriazole rings and two terminal chloride anions in a distorted tetrahedral arrangement as shown in Fig. 1. The angle between the two benzotriazole rings is 62.98 (7)°.

From Fig. 2, it is easy to see that the structure is consolidated by extensive C—H···O and O—H···O hydrogen bonds. This hydrogen bonding with the π-π stacking between neighboring results to the formation of three-dimensional structure.

Experimental

The ligand, 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetonitrile, was synthesized by the reaction of benzotriazole and bromoacetonitrile according to the procedure described in the literature (Danan et al. (1997)).

A mixture of 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetonitrile (32 mg, 0.2 mmol), ZnCl₂(40 mg, 0.3 mmol), ethanol(1 ml) and a few drops of water sealed in a glass tube maintained at 120 °C. Colorless crystals suitable for X-ray analysis were obtained after several days.