4-({[4-Amino-5-(4-chloro­anilinometh­yl)-4H-1,2,4-triazol-3-yl]sulfan­yl}acet­yl)-3-(4-meth­oxy­phen­yl)-1,2,3-oxadiazol-3-ium-5-olate

Hoong-Kun Fun; Madhukar Hemamalini; Nithinchandra; Balakrishna Kalluraya

doi:10.1107/S1600536810046155

. 2010 Nov 13;66(Pt 12):o3178. doi: 10.1107/S1600536810046155

4-({[4-Amino-5-(4-chloroanilinomethyl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetyl)-3-(4-methoxyphenyl)-1,2,3-oxadiazol-3-ium-5-olate

Hoong-Kun Fun ^a,^*,^‡, Madhukar Hemamalini ^a, Nithinchandra ^b, Balakrishna Kalluraya ^b

PMCID: PMC3011622 PMID: 21589473

Abstract

In the title sydnone compound, C₂₀H₁₈ClN₇O₄S, the oxadiazole, triazole, chloro-substituted and methoxy-substituted phenyl rings are essentially planar, with maximum deviations of 0.007 (3), 0.009 (2), 0.017 (2) and 0.002 (3) Å, respectively. The dihedral angles between the chloro-substituted phenyl ring and the triazole ring, the triazole ring and the oxadiazole ring, and the oxadiazole ring and the methoxy-substituted phenyl ring are 80.02 (13), 85.68 (14) and 51.62 (14)°, respectively. In the crystal, molecules are connected via intermolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds, forming sheets lying parallel to the ac plane.

Related literature

For details and biological applications of sydnones, see: Rai et al. (2008 ▶); Jyothi et al. (2008 ▶); Kalluraya et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₀H₁₈ClN₇O₄S
M _r = 487.92
Monoclinic,
a = 20.109 (3) Å
b = 5.8952 (8) Å
c = 36.369 (5) Å
β = 96.076 (3)°
V = 4287.2 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 K
0.40 × 0.13 × 0.04 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T _min = 0.883, T _max = 0.989
8905 measured reflections
4429 independent reflections
3255 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.132
S = 1.08
4429 reflections
311 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.35 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 datablocks global, I. DOI: 10.1107/S1600536810046155/rz2514sup1.cif

e-66-o3178-sup1.cif^{(23.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046155/rz2514Isup2.hkl

e-66-o3178-Isup2.hkl^{(212.7KB, 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
N6—H1N6⋯N4ⁱ	0.93 (3)	2.08 (3)	2.947 (3)	155 (2)
N7—H1N7⋯O3ⁱⁱ	0.86 (3)	2.22 (3)	2.990 (3)	150 (3)
N6—H2N6⋯O2ⁱⁱⁱ	0.90 (3)	2.15 (3)	2.983 (3)	153 (2)
C4—H4A⋯O4^iv	0.93	2.53	3.337 (3)	145

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

Acknowledgments

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

Sydnones are mesoionic heterocyclic aromatic compounds. The study of sydnones still remains a field of interest because of their electronic structures and also because of the varied types of biological activities (Rai et al., 2008). Recently sydnone derivatives were found to exhibit promising antimicrobial properties (Kalluraya et al., 2002). Since their discovery, sydnones have shown diverse biological activities and it is thought that the meso-ionic nature of the sydnone ring promotes significant interactions with biological systems. Because of the wide variety of properties displayed by sydnones, we were prompted to synthesize a new S-substituted triazoles containing a sydnone ring. Photochemical bromination of 3-aryl-4-acetylsydnone afforded 3-aryl-4 bromoacetylsydnones. Condensation of 3-substituted-4-amino-5-mecapto-1,2,4-triazoles with 3-aryl-4-bromoacetylsydnones yielded S-substituted triazoles derivatives (Jyothi et al., 2008).

In the title compound, (Fig. 1), the rings A (C14–C19), B (N3/N4/N5/C11–C12), C (N1/N2/O1/C7–C8) and D (C1–C6) are essentially planar. The dihedral angle between the best planes of the rings are A/B = 80.02 (13)°, A/C = 53.76 (14)°, A/D = 5.24 (12)°, B/C = 85.68 (14)°, B/D = 85.12 (13)° and C/D = 51.62 (14)°. The bond lengths (Allen et al., 1987) and angles are normal.

In the crystal structure (Fig. 2), the molecules are connected via intermolecular N6—H1N6···N4, N7—H1N7···O3, N6—H2N6···O2 and C4—H4A···O4 hydrogen bonds to form two-dimensional networks parallel to the ac plane.

Experimental

A catalytic amount of anhydrous sodium acetate was added to solution of 4-bromoacetyl-3-(p-anisyl)sydnone (0.01 mol) and 4-amino-5-(p-chlorophenyl) aminomethyl-4H-1,2,4-triazole-3-thiol (0.01 mol) in ethanol. The solution was stirred at room temperature for 2-3 hours. The solid product which separated was filtered and dried. It was then recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained from a mixture of DMF and ethanol (1:2 v/v) by slow evaporation.