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

Asiri, A.M.; Faidallah, H.M.; Al-Youbi, A.O.; Obaid, A.Y.; Ng, S.W.

doi:10.1107/S1600536811034325

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2466

doi:10.1107/S1600536811034325

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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 Abdullah.Y. Obaid ^a and Seik Weng Ng ^b,^a ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 6 August 2011; accepted 21 August 2011; online 27 August 2011)

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, F d d 2
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[F² > 2σ(F²)] = 0.033
wR(F²) = 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)

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)
Symmetry codes: (i) x, y, z+1; (ii) $[-x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034325/xu5287sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811034325/xu5287Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₃H₁₂N₄O₄S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₁₃H₁₂N₄O₄S	F(000) = 2656
M_r = 320.33	D_x = 1.604 Mg m⁻³
Orthorhombic, Fdd2	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: F 2 -2d	Cell parameters from 5872 reflections
a = 18.0113 (4) Å	θ = 4.9–74.4°
b = 35.5302 (11) Å	µ = 2.43 mm⁻¹
c = 8.2900 (2) Å	T = 100 K
V = 5305.1 (2) Å³	Plate, colorless
Z = 16	0.30 × 0.20 × 0.05 mm

Data collection top

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	1886 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1870 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.032
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.5°, θ_min = 5.0°
ω scan	h = −42→44
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −22→22
T_min = 0.529, T_max = 0.888	l = −10→7
7699 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0772P)² + 4.3892P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
1886 reflections	Δρ_max = 0.41 e Å⁻³
207 parameters	Δρ_min = −0.35 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 441 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.026 (18)

Crystal data top

C₁₃H₁₂N₄O₄S	V = 5305.1 (2) Å³
M_r = 320.33	Z = 16
Orthorhombic, Fdd2	Cu Kα radiation
a = 18.0113 (4) Å	µ = 2.43 mm⁻¹
b = 35.5302 (11) Å	T = 100 K
c = 8.2900 (2) Å	0.30 × 0.20 × 0.05 mm

Data collection top

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	1886 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1870 reflections with I > 2σ(I)
T_min = 0.529, T_max = 0.888	R_int = 0.032
7699 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	Δρ_max = 0.41 e Å⁻³
S = 1.08	Δρ_min = −0.35 e Å⁻³
1886 reflections	Absolute structure: Flack (1983), 441 Friedel pairs
207 parameters	Absolute structure parameter: 0.026 (18)
1 restraint

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.12413 (3)	0.212823 (15)	0.43880 (7)	0.01769 (17)
O1	0.21513 (9)	0.37146 (4)	−0.5296 (2)	0.0193 (4)
O2	0.05983 (9)	0.28881 (4)	−0.2671 (2)	0.0188 (4)
O3	0.17529 (10)	0.22599 (5)	0.5595 (2)	0.0235 (4)
N4	0.04217 (11)	0.22369 (5)	0.5034 (3)	0.0213 (4)
N1	0.14841 (11)	0.36838 (5)	−0.6234 (3)	0.0200 (4)
N2	0.17467 (10)	0.30278 (5)	−0.1592 (3)	0.0154 (4)
N3	0.24011 (10)	0.32316 (5)	−0.1526 (3)	0.0163 (4)
O4	0.12339 (11)	0.17367 (5)	0.3966 (3)	0.0277 (5)
C1	0.32798 (13)	0.36781 (6)	−0.2608 (3)	0.0204 (5)
H1A	0.3547	0.3612	−0.1618	0.031*
H1B	0.3168	0.3948	−0.2603	0.031*
H1C	0.3589	0.3618	−0.3546	0.031*
C2	0.25679 (12)	0.34585 (6)	−0.2694 (3)	0.0170 (5)
C3	0.20621 (12)	0.34980 (6)	−0.3997 (3)	0.0169 (5)
C4	0.13880 (13)	0.33186 (6)	−0.4030 (3)	0.0156 (5)
C5	0.10469 (13)	0.34528 (6)	−0.5465 (3)	0.0177 (5)
C6	0.02971 (13)	0.33542 (7)	−0.6145 (3)	0.0213 (5)
H6A	0.0218	0.3492	−0.7153	0.032*
H6B	−0.0090	0.3423	−0.5367	0.032*
H6C	0.0275	0.3083	−0.6357	0.032*
C7	0.11926 (12)	0.30620 (6)	−0.2766 (3)	0.0155 (5)
C8	0.16360 (12)	0.28011 (6)	−0.0177 (3)	0.0159 (5)
C9	0.18337 (13)	0.29491 (6)	0.1314 (3)	0.0175 (5)
H9	0.2040	0.3195	0.1383	0.021*
C10	0.17290 (12)	0.27382 (6)	0.2696 (3)	0.0175 (5)
H10	0.1876	0.2835	0.3715	0.021*
C11	0.14063 (12)	0.23826 (6)	0.2583 (3)	0.0171 (5)
C12	0.12297 (12)	0.22293 (7)	0.1099 (4)	0.0189 (5)
H12	0.1026	0.1983	0.1037	0.023*
C13	0.13496 (12)	0.24347 (6)	−0.0300 (3)	0.0174 (5)
H13	0.1240	0.2329	−0.1325	0.021*
H1	0.0433 (17)	0.2472 (9)	0.559 (4)	0.025 (8)*
H2	0.008 (2)	0.2165 (10)	0.439 (6)	0.043 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0235 (3)	0.0179 (3)	0.0117 (3)	−0.00015 (18)	−0.0010 (2)	0.0027 (2)
O1	0.0226 (8)	0.0227 (7)	0.0124 (9)	−0.0015 (6)	0.0005 (7)	0.0035 (7)
O2	0.0198 (8)	0.0231 (7)	0.0135 (9)	−0.0028 (5)	−0.0009 (7)	0.0002 (7)
O3	0.0273 (9)	0.0289 (8)	0.0143 (10)	−0.0008 (7)	−0.0034 (8)	0.0049 (7)
N4	0.0219 (10)	0.0270 (10)	0.0150 (11)	−0.0041 (8)	−0.0011 (9)	0.0002 (9)
N1	0.0230 (9)	0.0225 (9)	0.0145 (11)	0.0025 (7)	−0.0033 (9)	0.0000 (8)
N2	0.0190 (8)	0.0174 (8)	0.0098 (10)	−0.0005 (7)	0.0018 (8)	0.0000 (8)
N3	0.0183 (9)	0.0169 (7)	0.0136 (10)	0.0005 (7)	0.0002 (8)	−0.0033 (8)
O4	0.0464 (11)	0.0194 (8)	0.0172 (11)	0.0006 (7)	−0.0003 (8)	0.0042 (8)
C1	0.0236 (10)	0.0242 (10)	0.0134 (13)	−0.0058 (8)	0.0020 (11)	−0.0016 (9)
C2	0.0208 (10)	0.0163 (8)	0.0139 (12)	0.0009 (8)	0.0016 (10)	−0.0015 (8)
C3	0.0219 (10)	0.0166 (9)	0.0123 (12)	0.0003 (8)	0.0025 (10)	−0.0015 (9)
C4	0.0201 (10)	0.0171 (9)	0.0096 (12)	0.0017 (8)	0.0007 (9)	−0.0015 (9)
C5	0.0220 (10)	0.0202 (9)	0.0107 (12)	0.0031 (8)	0.0020 (10)	0.0003 (9)
C6	0.0220 (11)	0.0291 (11)	0.0128 (12)	0.0017 (8)	−0.0028 (10)	0.0024 (10)
C7	0.0195 (10)	0.0164 (9)	0.0107 (13)	0.0032 (7)	0.0005 (9)	−0.0007 (9)
C8	0.0170 (9)	0.0176 (9)	0.0130 (13)	0.0022 (7)	0.0013 (10)	0.0015 (9)
C9	0.0220 (10)	0.0176 (10)	0.0127 (12)	−0.0001 (8)	0.0001 (10)	−0.0016 (9)
C10	0.0223 (10)	0.0195 (10)	0.0107 (11)	0.0017 (8)	0.0003 (10)	−0.0007 (9)
C11	0.0179 (9)	0.0186 (10)	0.0147 (13)	0.0027 (8)	0.0016 (10)	0.0030 (10)
C12	0.0210 (11)	0.0171 (9)	0.0186 (14)	0.0000 (8)	−0.0009 (10)	−0.0022 (10)
C13	0.0212 (10)	0.0189 (10)	0.0122 (13)	0.0004 (8)	−0.0022 (9)	−0.0023 (9)

Geometric parameters (Å, º) top

S1—O4	1.4345 (19)	C2—C3	1.420 (3)
S1—O3	1.4385 (19)	C3—C4	1.372 (3)
S1—N4	1.617 (2)	C4—C5	1.422 (4)
S1—C11	1.773 (3)	C4—C7	1.433 (3)
O1—C3	1.333 (3)	C5—C6	1.505 (3)
O1—N1	1.435 (3)	C6—H6A	0.9800
O2—C7	1.238 (3)	C6—H6B	0.9800
N4—H1	0.95 (3)	C6—H6C	0.9800
N4—H2	0.85 (5)	C8—C9	1.389 (4)
N1—C5	1.304 (3)	C8—C13	1.404 (3)
N2—N3	1.384 (3)	C9—C10	1.382 (3)
N2—C7	1.399 (3)	C9—H9	0.9500
N2—C8	1.437 (3)	C10—C11	1.394 (3)
N3—C2	1.296 (3)	C10—H10	0.9500
C1—C2	1.502 (3)	C11—C12	1.383 (4)
C1—H1A	0.9800	C12—C13	1.387 (4)
C1—H1B	0.9800	C12—H12	0.9500
C1—H1C	0.9800	C13—H13	0.9500

O4—S1—O3	119.41 (11)	N1—C5—C4	111.0 (2)
O4—S1—N4	107.69 (11)	N1—C5—C6	120.4 (2)
O3—S1—N4	106.07 (12)	C4—C5—C6	128.5 (2)
O4—S1—C11	106.85 (12)	C5—C6—H6A	109.5
O3—S1—C11	108.30 (11)	C5—C6—H6B	109.5
N4—S1—C11	108.10 (11)	H6A—C6—H6B	109.5
C3—O1—N1	107.01 (16)	C5—C6—H6C	109.5
S1—N4—H1	110.4 (18)	H6A—C6—H6C	109.5
S1—N4—H2	112 (3)	H6B—C6—H6C	109.5
H1—N4—H2	125 (3)	O2—C7—N2	121.9 (2)
C5—N1—O1	106.8 (2)	O2—C7—C4	125.2 (2)
N3—N2—C7	126.1 (2)	N2—C7—C4	112.9 (2)
N3—N2—C8	112.27 (18)	C9—C8—C13	120.6 (2)
C7—N2—C8	121.16 (18)	C9—C8—N2	118.59 (18)
C2—N3—N2	119.6 (2)	C13—C8—N2	120.8 (2)
C2—C1—H1A	109.5	C10—C9—C8	119.8 (2)
C2—C1—H1B	109.5	C10—C9—H9	120.1
H1A—C1—H1B	109.5	C8—C9—H9	120.1
C2—C1—H1C	109.5	C9—C10—C11	119.5 (2)
H1A—C1—H1C	109.5	C9—C10—H10	120.2
H1B—C1—H1C	109.5	C11—C10—H10	120.2
N3—C2—C3	118.8 (2)	C12—C11—C10	120.8 (2)
N3—C2—C1	119.0 (2)	C12—C11—S1	120.77 (17)
C3—C2—C1	122.2 (2)	C10—C11—S1	118.4 (2)
O1—C3—C4	111.0 (2)	C11—C12—C13	120.0 (2)
O1—C3—C2	126.5 (2)	C11—C12—H12	120.0
C4—C3—C2	122.5 (2)	C13—C12—H12	120.0
C3—C4—C5	104.1 (2)	C12—C13—C8	119.0 (2)
C3—C4—C7	119.9 (2)	C12—C13—H13	120.5
C5—C4—C7	136.0 (2)	C8—C13—H13	120.5

C3—O1—N1—C5	−0.6 (2)	C3—C4—C7—O2	179.4 (2)
C7—N2—N3—C2	−5.6 (3)	C5—C4—C7—O2	−1.1 (4)
C8—N2—N3—C2	−177.91 (19)	C3—C4—C7—N2	0.3 (3)
N2—N3—C2—C3	1.5 (3)	C5—C4—C7—N2	179.9 (2)
N2—N3—C2—C1	179.99 (19)	N3—N2—C8—C9	38.9 (3)
N1—O1—C3—C4	1.5 (2)	C7—N2—C8—C9	−133.9 (2)
N1—O1—C3—C2	−176.5 (2)	N3—N2—C8—C13	−139.7 (2)
N3—C2—C3—O1	−179.1 (2)	C7—N2—C8—C13	47.5 (3)
C1—C2—C3—O1	2.4 (4)	C13—C8—C9—C10	−1.8 (3)
N3—C2—C3—C4	3.2 (3)	N2—C8—C9—C10	179.60 (19)
C1—C2—C3—C4	−175.3 (2)	C8—C9—C10—C11	−1.8 (3)
O1—C3—C4—C5	−1.7 (2)	C9—C10—C11—C12	3.8 (3)
C2—C3—C4—C5	176.3 (2)	C9—C10—C11—S1	−177.18 (17)
O1—C3—C4—C7	177.95 (19)	O4—S1—C11—C12	24.3 (2)
C2—C3—C4—C7	−4.0 (3)	O3—S1—C11—C12	154.11 (18)
O1—N1—C5—C4	−0.5 (3)	N4—S1—C11—C12	−91.4 (2)
O1—N1—C5—C6	−179.15 (19)	O4—S1—C11—C10	−154.73 (18)
C3—C4—C5—N1	1.3 (3)	O3—S1—C11—C10	−24.9 (2)
C7—C4—C5—N1	−178.2 (2)	N4—S1—C11—C10	89.6 (2)
C3—C4—C5—C6	179.9 (2)	C10—C11—C12—C13	−2.2 (3)
C7—C4—C5—C6	0.3 (4)	S1—C11—C12—C13	178.81 (17)
N3—N2—C7—O2	−174.6 (2)	C11—C12—C13—C8	−1.4 (3)
C8—N2—C7—O2	−2.9 (3)	C9—C8—C13—C12	3.4 (3)
N3—N2—C7—C4	4.5 (3)	N2—C8—C13—C12	−178.04 (19)
C8—N2—C7—C4	176.19 (19)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x, y, z+1; (ii) −x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₄O₄S
M_r	320.33
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	100
a, b, c (Å)	18.0113 (4), 35.5302 (11), 8.2900 (2)
V (Å³)	5305.1 (2)
Z	16
Radiation type	Cu Kα
µ (mm⁻¹)	2.43
Crystal size (mm)	0.30 × 0.20 × 0.05

Data collection
Diffractometer	Agilent Technologies SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.529, 0.888
No. of measured, independent and observed [I > 2σ(I)] reflections	7699, 1886, 1870
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.096, 1.08
No. of reflections	1886
No. of parameters	207
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.35
Absolute structure	Flack (1983), 441 Friedel pairs
Absolute structure parameter	0.026 (18)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) x, y, z+1; (ii) −x, −y+1/2, z+1/2.

Acknowledgements

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

References

Abdel-Aziz, H. A., Bari, A. & Ng, S. W. (2010). Acta Cryst. E66, o3344. CrossRef IUCr Journals Google Scholar
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Faid-Allah, H. S., Khan, K. A. & Makki, M. S. (2011). J. Chin. Chem. Soc. 58, 191–198. CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Makki, M. S. & Faid-Allah, H. S. (1996). J. Chin. Chem. Soc. 43, 433–438. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Page o2466

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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