4-(3,7-Dimethyl-4-oxo-4,5-dihydro-isoxazolo[4,5-d]pyridazin-5-yl)benzene-sulfonamide.

The nine-membered fused-ring system of the title pyridazine derivative, C(13)H(12)N(4)O(4)S, is approximately planar (r.m.s. deviation 0.027 Å), and the benzene ring of the phenyl-sulfamide 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 mol-ecules 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 = 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

Δρmax = 0.41 e Å−3

Δρmin = −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 ▶).

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

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

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

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

C13H12N4O4S	F(000) = 2656
Mr = 320.33	Dx = 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

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	Rint = 0.032
Detector resolution: 10.4041 pixels mm-1	θmax = 74.5°, θmin = 5.0°
ω scan	h = −42→44
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −22→22
Tmin = 0.529, Tmax = 0.888	l = −10→7
7699 measured reflections

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(Fo2) + (0.0772P)2 + 4.3892P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1886 reflections	Δρmax = 0.41 e Å−3
207 parameters	Δρmin = −0.35 e Å−3
1 restraint	Absolute structure: Flack (1983), 441 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.026 (18)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) .