Bis(4-amino­benzoato)-κ2 O,O′;κO-(2,2′-bipyridine-κ2 N,N′)zinc

Miao-Ling Huang; Ling-Ling Wang

doi:10.1107/S1600536811039389

. 2011 Sep 30;67(Pt 10):m1470. doi: 10.1107/S1600536811039389

Bis(4-aminobenzoato)-κ² O,O′;κO-(2,2′-bipyridine-κ² N,N′)zinc

Miao-Ling Huang ^a,^*, Ling-Ling Wang ^a

PMCID: PMC3201216 PMID: 22058723

Abstract

In the title complex, [Zn(C₇H₆NO₂)₂(C₁₀H₈N₂)], the Zn^II cation is coordinated by two aminobenzoate anions and one 2,2′-bipyridine ligand in a distorted trigonal–bipyramidal geometry. The carboxylate group of one aminobenzoate anion coordinates to the Zn^II cation in a monodentate manner, whereas the carboxylate group of the other aminobenzoate anion chelates the Zn cation with different Zn—O bond lengths. Intermolecular N—H⋯N and N—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of Zn complexes, see: Chohan & Naseer (2007 ▶); Huang et al. (2006 ▶); Ispir et al. (2006 ▶); Lo et al. (2007 ▶); Maria et al. (1996 ▶). For a related structure, see: Wang et al. (2005 ▶).

Experimental

Crystal data

[Zn(C₇H₆NO₂)₂(C₁₀H₈N₂)]
M _r = 493.81
Triclinic,
a = 7.9499 (14) Å
b = 10.7281 (19) Å
c = 13.905 (2) Å
α = 80.499 (2)°
β = 80.921 (2)°
γ = 70.538 (2)°
V = 1096.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 295 K
0.42 × 0.23 × 0.08 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.643, T _max = 0.914
8223 measured reflections
4058 independent reflections
3419 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.090
S = 1.07
4058 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039389/xu5334sup1.cif

e-67-m1470-sup1.cif^{(24.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039389/xu5334Isup2.hkl

e-67-m1470-Isup2.hkl^{(198.9KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Zn1—O1	1.9269 (18)
Zn1—O3	1.9704 (18)
Zn1—O4	2.395 (2)
Zn1—N3	2.124 (2)
Zn1—N4	2.088 (2)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯N2ⁱ	0.88	2.33	3.202 (4)	169
N1—H1E⋯O2ⁱⁱ	0.88	2.36	3.181 (4)	155
N2—H2E⋯O2ⁱⁱⁱ	0.88	2.28	3.116 (4)	159

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

Acknowledgments

This work was supported by the Education Department Foundation of Fujian Province of China (grant No. JK2011042).

supplementary crystallographic information

Comment

In recent decades, zinc complexes have received much attention because of their interesting with biological ligands to generate stable mixed coordinated complexes, which play a key role in life process such as anti-cancer, antiseptic and anti-inflammatory (Ispir et al., 2006; Chohan & Naseer, 2007; Huang et al., 2006; Lo et al., 2007). 4-Aminobenzoic acid as an important part in the folic acid, which is a constituent of the vitamin B complex and is found in animal and plant tissues, has been shown to be a growth factor in certain microorganisms (Maria et al., 1996). In order to extend further the study of 4-aminobenzoic acid ligand coordinate to zinc ion, we synthesized the title complex and determined the crystal structure.

The asymmetric unit of 1 contains one zinc cation, two 4-aminobenzoic ion, and one 2,2'-bipyridine molecule. The Zn(II) atom is five-coordinated, forming a distorted trigonal-bipyramidal (Table 1). In the coordination polyhedron, the equatorial plane is occupied by two O(O1,O3) atoms from different 4-aba and one N(N4) atom from 2,2'-bipyridine, at the apex is situated one O(O4) atom from 4-aba and one N(N3) atom from 2,2'-bipyridine (Fig 1). The Zn(II) center is coordinated by two types of 4-aba: one behaves in an unsymmetrical chelating mode [Zn—O(3) 1.9704 (18) and Zn—O(4) 2.395 (2) Å]; the other acts as a monodentate ligand through one carboxylate oxygen atom [Zn—O(1) 1.9269 (18) and Zn—O(2) 2.841 Å], which is similar to previously reported complex {[Zn₂(4,4'-bipy)₂(4-aba)₄](H₂O)₅} (Wang et al., 2005). The dihedral angle between phenyl rings of the two 4-aba is 81.83 (7)°.

Hydrogen bonds are observed between the molecules in the crystal structure (Table 2).

Experimental

An aqueous solution (5 ml) of ZnC₄H₆O₄.2H₂O (1 mmol) was added slowly to a mixed solution of 4-aminobenzoic acid (1.5 mmol) in H₂O (5 ml) and 2,2'-bipyridine (1 mmol) in ethanol (95%, 5 ml). After refluxing for 3 h, the mixture was filtered off while hot. The colourless single crystals suitable for X-ray analysis were obtained by slow evaporation of the above filtrate at room temperature after a month.