2,2′-(4-Methyl-4H-1,2,4-triazole-3,5-di­yl)dibenzene­sulfonamide

Tasleem Akhtar; Waseeq Ahmad Siddiqui; Adnan Ashraf; M Nawaz Tahir

doi:10.1107/S1600536812006113

. 2012 Feb 17;68(Pt 3):o754. doi: 10.1107/S1600536812006113

2,2′-(4-Methyl-4H-1,2,4-triazole-3,5-diyl)dibenzenesulfonamide

Tasleem Akhtar ^a, Waseeq Ahmad Siddiqui ^a, Adnan Ashraf ^a, M Nawaz Tahir ^b,^*

PMCID: PMC3295521 PMID: 22412632

Abstract

In the title compound, C₁₅H₁₅N₅O₄S₂, the dihedral angles between the central 1,2,4-triazole ring and the pendant benzene rings are 55.61 (10) and 68.59 (10)°; the dihedral angle between the benzene rings is 63.66 (9)°. Intramolecular N—H⋯N and N—H⋯O hydrogen bonds generate S(7) and S(12) rings, respectively. In the crystal, sheets extending in the (101) plane arise, with the molecules linked by C—H⋯O, N—H⋯N and N—H⋯O interactions. A C—H⋯π interaction further consolidates the structure.

Related literature

For background to benzisothiazole derivatives, see: Siddiqui et al. (2007 ▶); Siddiqui, Ahmad, Khan et al. (2008 ▶); Siddiqui, Ahmad, Siddiqui & Parvez (2008 ▶). For related crystal structures, see: Carlsen et al. (1995 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₅N₅O₄S₂
M _r = 393.44
Monoclinic,
a = 13.4190 (6) Å
b = 6.9043 (2) Å
c = 19.0498 (9) Å
β = 102.243 (2)°
V = 1724.80 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 296 K
0.35 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.915, T _max = 0.938
15158 measured reflections
4055 independent reflections
2526 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.158
S = 1.03
4055 reflections
239 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006113/hb6629sup1.cif

e-68-0o754-sup1.cif^{(26KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006113/hb6629Isup2.hkl

e-68-0o754-Isup2.hkl^{(194.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812006113/hb6629Isup3.cml

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

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

Cg1 and Cg3 are the centroids of the C7/N2/C8/N3/N4 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.82 (4)	2.33 (4)	3.082 (4)	153 (3)
N1—H1B⋯N4ⁱ	0.95 (4)	1.96 (4)	2.899 (4)	171 (3)
N5—H5A⋯O4ⁱⁱ	0.94 (4)	2.10 (4)	3.011 (4)	164 (3)
N5—H5B⋯N3	0.83 (4)	2.14 (4)	2.876 (4)	148 (4)
C9—H9B⋯O2ⁱⁱⁱ	0.96	2.17	2.990 (3)	142
C14—H14⋯Cg3^iv	0.93	2.68	3.583 (4)	163

Open in a new tab

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

In continuation to our research work on the synthesis of benzisothiazole derivatives (Siddiqui, Ahmad, Khan et al., 2008; Siddiqui, Ahmad, Siddiqui & Parvez, 2008), the title compound (I), (Fig. 1) is prepared from hydrazine and commercial source of saccharin.

The crystal structures of 4-methyl-3,5-diphenyl-4H-1,2,4-triazolethe has been published which is also related to (I).

In (I), the phenyl rings A (C1–C6), B (C10—C15) and the 4-methyl-4H- 1,2,4-triazole moiety C (C7–C9/N2–N4) are planar with r. m. s. deviation of 0.0079 Å, 0.0051 Å and 0.0310 Å, respectively. The dihedral angle between A/B, A/C and B/C is 63.66 (9)°, 68.59 (1)° and 55.61 (10)°, respectively. There exist intramolecular H-bonding of N—H···N and N—H···O types (Table 1, Fig. 1) forming S (7) and S (12) ring motifs (Bernstein et al., 1995), respectively. There exist intermolecular H-bondings of C—H···.O, N—H···N and N—H···O types (Table 1, Fig. 2) which consolidates the molecules in the form two-dimensional polymeric network extending along the (101) plane. There exist C—H···π (Table 1) interactions which also play role in establishing the structure.

Experimental

For the synthesis of title compound, hydrazine monohydrate and saccharin were used as the starting materials following a reported procedure (Siddiqui et al., 2007). Colourless needles of (I) suitable for X-ray crystallographic study were grown from methanol at room temperature. m. p. = 483–484 K. FT—IR: (KBr, cm^-1): 3296, 3263 (NH and NH₂), 2987 (Ar. CH), 1651 (C═ N), 1541 (NH def.), 1454 (CH def.), 1315, 1151 (SO₂).