(2,2′-Biquinoline-κ2 N,N′)dibromido­zinc(II)

Hamideh Saravani; Ali Reza Rezvani; Niloufar Akbarzadeh Torbati

doi:10.1107/S1600536810047434

. 2010 Nov 24;66(Pt 12):m1622–m1623. doi: 10.1107/S1600536810047434

(2,2′-Biquinoline-κ² N,N′)dibromidozinc(II)

Hamideh Saravani ^a,^*, Ali Reza Rezvani ^a, Niloufar Akbarzadeh Torbati ^a

PMCID: PMC3011677 PMID: 21589297

Abstract

In the title compound, [ZnBr₂(C₁₈H₁₂N₂)], the Zn^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from the 2,2′-biquinoline ligand and two terminal Br atoms. The crystal packing is stabilized by weak intermolecular C—H⋯Br hydrogen bonds and extensive intermolecular π–π contacts between the pyridine and benzene rings [centroid–centroid distances = 3.775 (4), 3.748 (4), 3.735 (4), 3.538 (4), 3.678 (4) and 3.513 (4) Å].

Related literature

For Zn—Br and Zn—N bond lengths in related structures, see: Alizadeh et al. (2009 ▶), Muranishi et al. (2005 ▶). For complexes of 2,2′-biquinoline, see: Bowmaker et al. (2005 ▶); Butcher & Sinn (1977 ▶); Kou et al. (2008 ▶); Moreno et al. (2007 ▶); Okabe & Muranishi (2005 ▶); Rahimi et al. (2009 ▶); Yoshikawa et al. (2003 ▶); Zhou & Ng (2006 ▶).

Experimental

Crystal data

[ZnBr₂(C₁₈H₁₂N₂)]
M _r = 481.49
Monoclinic,
a = 7.9188 (16) Å
b = 12.351 (3) Å
c = 17.385 (4) Å
β = 103.01 (3)°
V = 1656.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 6.31 mm⁻¹
T = 298 K
0.20 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T _min = 0.380, T _max = 0.530
13476 measured reflections
4471 independent reflections
2968 reflections with I > 2σ(I)
R _int = 0.098

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.150
S = 1.15
4471 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 1.14 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047434/jj2062sup1.cif

e-66-m1622-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047434/jj2062Isup2.hkl

e-66-m1622-Isup2.hkl^{(219.1KB, hkl)}

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

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

N1—Zn1	2.063 (4)
N2—Zn1	2.056 (5)
Zn1—Br2	2.3348 (11)
Zn1—Br1	2.3498 (12)

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N2—Zn1—N1	80.56 (18)
N2—Zn1—Br2	112.49 (14)
N1—Zn1—Br2	116.75 (13)
N2—Zn1—Br1	113.58 (14)
N1—Zn1—Br1	107.98 (15)
Br2—Zn1—Br1	119.24 (4)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Br2ⁱ	0.93	2.87	3.574 (7)	133

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to the University of Sistan and Baluchestan for financial support.

supplementary crystallographic information

Comment

Numerous complexes have been prepared with the bidentate ligand 2,2'-biquinoline (2,2'-biq) such as that of iron (Rahimi et al., 2009), iridium (Yoshikawa et al., 2003), platinum (Okabe & Muranishi 2005), copper (Moreno et al., 2007; Zhou & Ng 2006), silver (Bowmaker et al., 2005), nickel (Kou et al., 2008; Butcher & Sinn 1977) and palladium (Muranishi et al., 2005). For further investigation of 2,2'-biquinoline, we have synthesized the title compound, [ZnBr₂(C₁₈H₁₂N₂)].

In the title compound, the Zn^II atom is four-coordinate in a distorted tetrahedral configuration with two N atoms from one 2,2'-biquinoline and two terminal Br atoms (Fig. 1). The Zn—N and Zn—Br bond lengths and angles are within the normal ranges for [ZnCl₂(biq)] (Muranishi et al., 2005) and [ZnBr₂(6,6'-dmbpy)], (Alizadeh et al., 2009) [where 6,6'-dmbpy is 6,6'-dimethyl-2, 2'-bipyridine], respectively. Crystal stability is enhanced by weak intermolecular C—H···Br hydrogen bonds (Table 2, Fig.2) and extensive weak π—π intermolecular contacts between the mean planes of the pyridine and phenyl rings (Table 3).

Experimental

For the preparation of the title compound, a solution of 2,2'- biquinoline (0.51 g, 2.0 mmol) in methanol (10 ml) and chloroform (10 ml) was added to a solution of ZnBr₂ (0.46 g, 2.0 mmol) in methanol (5 ml) and chloroform (5 ml) and the resulting solution was stirred for 20 min at room temperature. Suitable crystals for X-ray diffraction experiment were obtained by methanol diffusion into a solution in DMSO after one week (yield; 0.72 g, 74.8%).