Crystal structure of poly[di-μ-aqua-{5-[(1Z)-2-(4-chloro­phen­yl)-1-cyano­ethenyl]-1,2,3,4-tetra­zol-1-ido-κN 1}sodium]

Joel T Mague; Shaaban K Mohamed; Mehmet Akkurt; Ahmed M M El-Saghier; Mustafa R Albayati

doi:10.1107/S2056989015006325

. 2015 Apr 9;71(Pt 5):m102–m103. doi: 10.1107/S2056989015006325

Crystal structure of poly[di-μ-aqua-{5-[(1Z)-2-(4-chlorophenyl)-1-cyanoethenyl]-1,2,3,4-tetrazol-1-ido-κN ¹}sodium]

Joel T Mague ^a, Shaaban K Mohamed ^b,^c, Mehmet Akkurt ^d, Ahmed M M El-Saghier ^e, Mustafa R Albayati ^f,^*

PMCID: PMC4420058 PMID: 25995885

Abstract

In the title compound, [Na(C₁₀H₅ClN₅)(H₂O)₂]_n, infinite chains of [Na(H₂O)₂]⁺ cations having a diamond-shaped cross-section and running parallel to the b axis are formed. O—H⋯N hydrogen bonds to the anions generate layers parallel to (100) which have the chlorobenzenecyanoethenyl substituents protruding from both surfaces. The sodium ion makes a short contact of 2.4801 (13) Å with the N atom of the tetrazolide ring which is syn to the cyano N atom.

Keywords: crystal structure, sodium salt, tetrazoles, hydrogen bonding

Related literature

For chemical behaviour of tetrazoles, see: Smith et al. (1991 ▸); Duncia et al. (1990 ▸). For various industrial applications of different tetrazole derivatives, see: Modarresi et al. (2009 ▸); Singh et al. (1980 ▸). For medicinal activities of compounds with a tetrazole scaffold, see: Myznikov et al. (2007 ▸); Schocken et al. (1989 ▸); Mekni & Bakloiti (2008 ▸); Lim et al. (2007 ▸).

Experimental

Crystal data

[Na(C₁₀H₅ClN₅)(H₂O)₂]
M _r = 289.66
Monoclinic,
a = 22.0438 (4) Å
b = 3.8343 (1) Å
c = 15.0141 (3) Å
β = 92.427 (1)°
V = 1267.89 (5) Å³
Z = 4
Cu Kα radiation
μ = 3.08 mm⁻¹
T = 150 K
0.29 × 0.11 × 0.04 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T _min = 0.73, T _max = 0.89
9115 measured reflections
2560 independent reflections
2249 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.086
S = 1.03
2560 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015006325/tk5364sup1.cif

e-71-0m102-sup1.cif^{(305.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006325/tk5364Isup2.hkl

e-71-0m102-Isup2.hkl^{(140.7KB, hkl)}

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015006325/tk5364fig1.tif

Title compound with numbering scheme and 50% probability ellipsoids.

Click here for additional data file.^{(1.1MB, tif)}

2 2 + n x y z x y z x y z x y z x y z x y z . DOI: 10.1107/S2056989015006325/tk5364fig2.tif

A portion of the {[Na(H₂O)₂]⁺}_n chain (symmetry operations: (i) x, 1 + y, z, (ii) 2 − x, Inline graphic + y, − z, (iii) x, −1 + y, z, (iv) 2 − x, − + y, − z, (v) 2 − x, − + y, − z, (vi) x, −2 + y, z).

Click here for additional data file.^{(1.8MB, tif)}

b . DOI: 10.1107/S2056989015006325/tk5364fig3.tif

Packing viewed along the b axis.

Click here for additional data file.^{(1.5MB, tif)}

. DOI: 10.1107/S2056989015006325/tk5364fig4.tif

Elevation view of the chain structure.

CCDC reference: 1056677

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O1H1AN3ⁱ	0.84	2.04	2.8443(17)	160
O1H1BN2ⁱⁱ	0.84	2.02	2.8593(17)	175
O2H2BN5	0.84	2.44	3.1009(19)	136

Open in a new tab

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

Acknowledgments

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

supplementary crystallographic information

S1. Comment

Tetrazole compounds have been largely associated with a wide range of applications in medicine, biochemistry and agriculture (Modarresi et al., 2009; Singh et al., 1980). The medicinal activity of the tetrazole functionality is due to its ability to serve as a bioequivalent (bioisostere) of the carboxylic acid group (Smith et al., 1991; Duncia et al., 1990). They are also used as anti-hypertensive, anti-allergic, anti-biotic and anti-convulsant agents (Myznikov et al., 2007; Schocken et al., 1989; Mekni & Bakloiti, 2008; Lim et al., 2007). As part of our on-going study of bio-active molecules we herein report the synthesis and X-ray structure of the title compound as a building block precursor in the synthesis of new tetrazole scaffold compounds.

The title compound, Fig. 1, comprises infinite chains of [Na(H₂O)₂]⁺ cations having a diamond-shaped cross-section (Fig. 2) and running parallel to the b axis. These are associated on all four sides by tetrazoluide anions via O—H···N hydrogen bonds (Table 1) to generate layers parallel to (100) which have the chlorobenzenecyanoethenyl substituents protruding from both surfaces (Figs 3 and 4). Additionally, the sodium ion makes a contact of 2.4801 (13) Å with N4 of the tetrazolide ring which is significantly shorter than the sum of the ionic radius of Na⁺ and the van der Waals radius of N (2.71 Å). The C—N and N—N bond lengths in the ring (1.314 (2)–1.345 (2) Å) suggest significant delocalization of the negative charge. The hydrogen bonding interactions may restrict the cation to approach this site as opposed to the face of the ring. The tetrazolide and benzene rings, respectively, make dihedral angle of 4.8 (2) and 25.8 (2)° with the plane defined by C2–C4.

S2. Experimental

The title compound has been obtained as an unexpected product from a multi-component reaction of 1 mmol (94 mg) of amino-pyridine, 4-chloro-benzaldehyde (1 mmol, 141.5 mg), malononitrile (1 mmol, 66 mg), sodium acetate (0.15 mmol, 12.3 mg) and sodium azide (1 mmol, 65 mg). The reaction mixture was refluxed in ethanol/water (1:1) and monitored by TLC until completion after 3 hours. On cooling, the solid precipitate was collected, dried under vacuum and recrystallized from ethanol to afford suitable crystals for X-ray diffraction.