2,3,5-Triphenyl-2H-tetra­zol-3-ium iodide

Hoong-Kun Fun; Tze Shyang Chia; Gamal A E Mostafa; Mohamed M Abunassif; Hatem A Abdel-Aziz

doi:10.1107/S1600536812033661

. 2012 Aug 1;68(Pt 9):o2621. doi: 10.1107/S1600536812033661

2,3,5-Triphenyl-2H-tetrazol-3-ium iodide

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, Gamal A E Mostafa ^b, Mohamed M Abunassif ^b, Hatem A Abdel-Aziz ^b

PMCID: PMC3435649 PMID: 22969522

Abstract

The asymmetric unit of the title molecular salt, C₁₉H₁₅N₄ ⁺·I⁻, contains four 2,3,5-triphenyl-2H-tetrazol-3-ium cations and five iodide anions, with two of the latter lying on crystallographic inversion centres. In each cation, the tetrazole ring is essentially planar (r.m.s. deviations = 0.004–0.007 Å). The dihedral angles between the tetrazole ring and its three attached benzene rings in the four independent cations are: 12.9 (4), 67.0 (4), 48.1 (4); 20.8 (4), 51.1 (4), 62.3 (4); 11.4 (4), 52.3 (4), 47.3 (4) and 6.0 (4), 85.7 (4), 43.5 (4)°. A C—H⋯I hydrogen bond and C—H⋯π interactions are observed in the crystal.

Related literature

For the biological activity of the triphenyltetrazolium ion, see: Mostafa (2007 ▶); Hassanien et al. (2003 ▶); Abbas et al. (2001 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₉H₁₅N₄ ⁺·I⁻
M _r = 426.25
Monoclinic,
a = 9.6541 (4) Å
b = 30.9983 (14) Å
c = 24.3469 (10) Å
β = 97.930 (1)°
V = 7216.4 (5) Å³
Z = 16
Mo Kα radiation
μ = 1.78 mm⁻¹
T = 100 K
0.37 × 0.21 × 0.06 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T _min = 0.556, T _max = 0.907
71406 measured reflections
16492 independent reflections
13800 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.075
wR(F ²) = 0.172
S = 1.26
16492 reflections
868 parameters
H-atom parameters constrained
Δρ_max = 5.04 e Å⁻³
Δρ_min = −2.28 e Å⁻³

Data collection: APEX2 (Bruker, 2009) ▶; cell refinement: SAINT (Bruker, 2009) ▶; data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033661/hb6907sup1.cif

e-68-o2621-sup1.cif^{(65.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033661/hb6907Isup2.hkl

e-68-o2621-Isup2.hkl^{(806KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812033661/hb6907Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1C–C6C, C8C–C13C, C1A–C6A and C1D–C6D rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19B—H19B⋯I3	0.95	3.03	3.844 (8)	145
C3A—H3AA⋯Cg1ⁱ	0.95	2.87	3.636 (8)	138
C5A—H5AA⋯Cg2	0.95	2.89	3.547 (9)	127
C16A—H16A⋯Cg3ⁱⁱ	0.95	2.85	3.657 (9)	144
C16D—H16D⋯Cg4ⁱⁱⁱ	0.95	2.96	3.769 (10)	144

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

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University, for funding.

supplementary crystallographic information

Comment

2,3,5-Triphenyltetrazolium ion is used as indicator of bacterial dehydrogenase activity and as a reagent in colorimetric determination method for glucose dehydrogenase. It is also used as ion-pair reagent for determination of antimony in waste water (Mostafa, 2007; Hassanien et al., 2003; Abbas et al., 2001).

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit of the title compound, C₁₉H₁₅N₄⁺, I^-, contains four crystallographically independent 2,3,5-triphenyl-2H-tetrazol-3-ium cations, three fully occupied iodine anions (I1, I2 & I3) and two half-occupied iodine anions (I4 & I5). In the cation A, B, C and D, the tetrazole ring [N1–N4/C7] is essentially planar with r.m.s. deviations of 0.007, 0.007, 0.006 and 0.004 Å, respectively. The dihedral angles between the tetrazole ring and benzene rings [C1–C6, C8–C13 & C14–C19] are 12.9 (4), 67.0 (4) and 48.1 (4)° in cation A, 20.8 (4), 51.1 (4) and 62.3 (4)° in cation B, 11.4 (4), 52.3 (4) and 47.3 (4)° in cation C and 6.0 (4), 85.7 (4) and 43.5 (4)° in cation D.

In the crystal (Fig. 2), intermolecular C19B—H19B···I3 hydrogen bond and C—H···π interactions are observed, involving Cg1, Cg2, Cg3 and Cg4 which are the centroids of C1C–C6C, C8C–C13C, C1A–C6A and C1D–C6D rings, respectively.

Experimental

Upon the addition of triphenyltetrazolium chloride solution (50 ml, 1X10^-2M) to a solution of potassium iodide (50 ml), a yellowish precipitate was formed. The precipitate was filtered off, washed with cold deionized water until no chloride ions were detected in the washing solution. The precipitate was dried under vacuum to give the title ion-pair complex. Orange plates were obtained by slow evaporation of an ethanol solution.