4-(3,7-Dimethyl-4-oxo-4,5-dihydro­isoxazolo[4,5-d]pyridazin-5-yl)benzene­sulfonamide

Abdullah M Asiri; Hassan M Faidallah; Abdulrahman O Al-Youbi; AbdullahY Obaid; Seik Weng Ng

doi:10.1107/S1600536811034325

. 2011 Aug 27;67(Pt 9):o2466. doi: 10.1107/S1600536811034325

4-(3,7-Dimethyl-4-oxo-4,5-dihydroisoxazolo[4,5-d]pyridazin-5-yl)benzenesulfonamide

Abdullah M Asiri ^a, Hassan M Faidallah ^a, Abdulrahman O Al-Youbi ^a, AbdullahY Obaid ^a, Seik Weng Ng ^b,^a,^*

PMCID: PMC3200922 PMID: 22059027

Abstract

The nine-membered fused-ring system of the title pyridazine derivative, C₁₃H₁₂N₄O₄S, is approximately planar (r.m.s. deviation 0.027 Å), and the benzene ring of the phenylsulfamide substituent is aligned at 43.5 (1)° to the fused-ring system. The amine group of the sulfonamide substituent forms an N—H⋯O hydrogen bond to the ketonic O atom of two neigboring molecules to generate a chain running along the c axis.

Related literature

For a related structure, see: Abdel-Aziz et al. (2010 ▶). For the biological activity of the class of pyridazines, see: Faid-Allah et al. (2011 ▶); Makki & Faid-Allah (1996 ▶).

Experimental

Crystal data

C₁₃H₁₂N₄O₄S
M _r = 320.33
Orthorhombic,
a = 18.0113 (4) Å
b = 35.5302 (11) Å
c = 8.2900 (2) Å
V = 5305.1 (2) Å³
Z = 16
Cu Kα radiation
μ = 2.43 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.05 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.529, T _max = 0.888
7699 measured reflections
1886 independent reflections
1870 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.096
S = 1.08
1886 reflections
207 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ▶), 441 Friedel pairs
Flack parameter: 0.026 (18)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034325/xu5287sup1.cif

e-67-o2466-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034325/xu5287Isup2.hkl

e-67-o2466-Isup2.hkl^{(93.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034325/xu5287Isup3.cml

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
N4—H1⋯O2ⁱ	0.95 (3)	2.09 (4)	3.012 (3)	163 (3)
N4—H2⋯O2ⁱⁱ	0.85 (5)	2.11 (5)	2.933 (3)	162 (4)

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

Acknowledgments

We thank King Abdulaziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We have reported the synthesis of some pyridazines, which exhibit biological activity (Faid-Allah et al., 2011; Makki & Faid-Allah, 1996). There are few crystal structure reports of such systems; recently, we reported the crystal structure of 3-methyl-2-(4-methyl)-2H-pyrazolo[3,4-d]pyridazin-5-ium thiocyanate, a salt (Abdel-Aziz et al., 2010).

The nine-membered fused-ring system of C₁₃H₁₂N₄O₄S (Scheme I), is planar and the benzene ring of the phenylsufamido substitutent is aligned at 43.5 (1) ° (Fig. 1). The amino group the substitutent forms a hydrogen bond to the ketonic O atom of two neigboring molecules to generate a chain running along the c-axis of the orthorhombic unit cell (Table 1).

Experimental

A solution of ethyl 5-acetyl-3-methylisoxazole-4-carboxylate (0.39 g, 0.002 mol) in ethanol (25 ml) was refluxed with p-sulfonamidophenyl hydrazine hydrochloride (0.49 g, 0.002 mol) for 2 h. The pyridazine which separated after concentration of the reaction mixture was filtered off, washed with ethanol and recrystallized from the same solvent to give long thin prisms in 90% yield, m.p. 488 K.