trans-Bis(2-acet­amido-5-methyl­benzoato-κO 1)tetra­aqua­zinc

Jin-Feng Huang; Jian-You Zheng; Yu-Mei Dai

doi:10.1107/S1600536811012013

. 2011 Apr 7;67(Pt 5):m542. doi: 10.1107/S1600536811012013

trans-Bis(2-acetamido-5-methylbenzoato-κO ¹)tetraaquazinc

Jin-Feng Huang ^a, Jian-You Zheng ^a, Yu-Mei Dai ^a,^*

PMCID: PMC3089096 PMID: 21754280

Abstract

In the title compound, [Zn(C₁₀H₁₀NO₃)₂(H₂O)₄], the Zn^II atom lies on a crystallographic inversion center and is six-coordinated by two monodentate trans-related 2-(N-acetylamino)-5-methylbenzoato ligands and four water molecules, giving a slightly distorted octahedral geometry. There are two intramolecular hydrogen bonds [amine N—H⋯O_carboxyl and water O—H⋯O_carboxyl], while extensive intermolecular water O—H⋯O hydrogen-bonding interactions extend the complex units into a two-dimensional network structure along (100).

Related literature

The study of metal coordination polymers has enhanced our understanding of the relationship between molecular structure and material function, see: Dai et al. (2005 ▶); Moulton & Zaworotko (2001 ▶).

Experimental

Crystal data

[Zn(C₁₀H₁₀NO₃)₂(H₂O)₄]
M _r = 521.83
Monoclinic,
a = 19.300 (4) Å
b = 9.3000 (19) Å
c = 13.300 (3) Å
β = 107.60 (3)°
V = 2275.5 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 296 K
0.42 × 0.40 × 0.25 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.626, T _max = 0.752
10817 measured reflections
2130 independent reflections
1941 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.179
S = 1.11
2130 reflections
164 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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/S1600536811012013/zs2102sup1.cif

e-67-0m542-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012013/zs2102Isup2.hkl

e-67-0m542-Isup2.hkl^{(103.3KB, 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
N1—H1A⋯O1	0.86	1.95	2.616 (4)	133
O1W—H1WA⋯O2ⁱ	0.81 (2)	1.90 (2)	2.704 (4)	170 (5)
O1W—H1WB⋯O3ⁱⁱ	0.83 (2)	1.88 (2)	2.707 (4)	177 (4)
O2W—H2WA⋯O2ⁱ	0.80 (4)	2.12 (4)	2.916 (5)	172 (5)
O2W—H2WB⋯O3ⁱⁱⁱ	0.83 (4)	1.84 (3)	2.627 (4)	159 (5)

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

Acknowledgments

This work was supported financially by the Foundation of the Ministry of Education of Fujian Province (JB08037).

supplementary crystallographic information

Comment

In recent decades, the study of metal coordination polymers has witnessed tremendous growth as an attractive interface between synthetic chemistry and materials science, which significantly boosts the understanding of the relationship between molecular structure and material function (Moulton & Zaworotko, 2001; Dai et al., 2005). The crystal engineering of coordination polymers is highly influenced by the judicious choice of ligands, metal coordination geometry, template design and other subtle factors, such as counterions, solvent choice and reaction temperature. The deprotonated 2-(N-acetylamino)-5-methylbenzoic acid (HNB) ligands are good candidates in this respect for the construction of supramolecular architectures because in such bitopical ligands the N-acetyl group can act as a hydrogen-bond donor and/or acceptor, while the carboxyl function has strong coordination abilities with many metal ions. Taking these advantages into account, recently we have begun to assemble HNB and zinc ions into polymeric complexes under hydrothermal conditions. Herein, we report the synthesis and crystal structure of the title compound, [Zn(C₁₀H₁₀NO₃)₂(H₂O)₄] (I).

In the structure of (I) the Zn^II metal center lies on a crystallographic inversion center. The local coordination environment around Zn^II atom is slightly distorted octahedral, comprising two monodentate trans-related 2-(N-acetylamino)-5-methylbenzoato ligands and four water molecules (Fig. 1). Two intramolecular hydrogen bonds [amine N—H···O_carboxyl and water O—H···O_carboxyl] stabilize the complex units while extensive intermolecular water O—H···O_acetyl hydrogen-bonding interactions are observed in the structure (Table 1), giving rise to double-stranded chains. Further interactions involving the coordinated water ligands and the uncoordinated O atoms of the carboxyl group are gives a two-dimensional network structure (Fig. 2).

Experimental

ZnSO₄^.7H₂O (1.00 mmol, 0.28 g), 2-(N-acetylamino)-5-methylbenzoic acid (HNB) (1.00 mmol, 0.19 g) and NaOH (1.00 mmol, 0.04 g) were mixed in water (15 ml) and heated at 403 K for 3 days in a sealed 25 ml Teflon-lined stainless steel vessel under autogenous pressure. After cooling to room temperature at a rate of 5° C h^-1, yellow block crystals were isolated, washed with ethanol and then dried in air (33% yield).