4-(2,7-Dimethyl-4-oxo-1,3-thia­zolo[4,5-d]pyridazin-5-yl)benzene­sulfonamide

Asiri, A.M.; Faidallah, H.M.; Ng, S.W.

doi:10.1107/S1600536811021271

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1665

doi:10.1107/S1600536811021271

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4-(2,7-Dimethyl-4-oxo-1,3-thiazolo[4,5-d]pyridazin-5-yl)benzenesulfonamide

Abdullah M. Asiri,^a Hassan M. Faidallah ^a and Seik Weng Ng ^b ^*

^aChemistry Department, Faculty of Science, King Abdul Aziz University, Jeddah 21589, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 26 May 2011; accepted 2 June 2011; online 18 June 2011)

The thiazole–pyridazine fused-ring system of the title compound, C₁₃H₁₂N₄O₃S₂, is approximately planar (r.m.s. deviation = 0.037 Å); the benzene ring connected to the fused-ring system through the N atom is twisted by 39.3 (1)°. The amine group uses an H atom to form a hydrogen bond to the ketonic O atom of an inversion-related molecule to generate a dimer; adjacent dimers are linked by an N—H⋯O hydrogen bond to form a linear chain.

Related literature

For background to related compounds, see: Makki & Faidallah (1996 ).

Experimental

Crystal data

C₁₃H₁₂N₄O₃S₂
M_r = 336.39
Monoclinic, P 2₁ /c
a = 12.6048 (10) Å
b = 13.2273 (10) Å
c = 8.9703 (7) Å
β = 102.242 (1)°
V = 1461.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 100 K
0.20 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.928, T_max = 0.945
9962 measured reflections
3333 independent reflections
2888 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.097
S = 1.06
3333 reflections
209 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1⋯O1ⁱ	0.87 (1)	2.06 (1)	2.922 (2)	169 (2)
N4—H2⋯O2ⁱⁱ	0.88 (1)	2.38 (2)	3.090 (2)	139 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: 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/S1600536811021271/xu5226sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021271/xu5226Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811021271/xu5226Isup3.cml

checkCIF report

Comment top

This compound belongs to a class of tricyclic compounds posessing high antibacterial activity that are synthesized by reacting an aryl hydrazine with a thiazole that bears acetyl and carboxyl substituents on adjacent carbon atoms (Makki & Faidallah, 1996). A sulfonamido unit in the benzene ring of phenyl hydrazine should improved the activity. The thiazole–pyridazine fused-ring of C₁₃H₁₂N₄O₃S₂ (Scheme I, Fig. 1) is planar; the benzene ring that bears the sulfonamido unit is twisted by 39.3 (1)°. The amino group uses an H atom to form a hydrogen bond to the ketonic O atom of an inversion-related molecule to generate a dimer (Fig. 2); adjacent dimers are linked by a weaker N–H···O hydrogen bond to form a linear chain (Table 1).

Related literature top

For background on related compounds, see: Makki & Faidallah (1996).

Experimental top

Ethyl 5-acetyl-2-methylthiazole-4-carboxylate (0.40 g, 0.002 mol) in ethanol (25 ml) was heated with p-sulfonamidophenyl hydrazine hydrochloride (0.49 g, 0.002 mol) for 2 h. The pyridazine that separated was collected and recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 C₁₃H₁₂N₄O₃S₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded dimeric structure.

4-(2,7-dimethyl-4-oxo-1,3-thiazolo[4,5-d]pyridazin- 5-yl)benzenesulfonamide top

Crystal data top

C₁₃H₁₂N₄O₃S₂	F(000) = 696
M_r = 336.39	D_x = 1.529 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3931 reflections
a = 12.6048 (10) Å	θ = 2.3–28.2°
b = 13.2273 (10) Å	µ = 0.38 mm⁻¹
c = 8.9703 (7) Å	T = 100 K
β = 102.242 (1)°	Block, light brown
V = 1461.6 (2) Å³	0.20 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3333 independent reflections
Radiation source: fine-focus sealed tube	2888 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→16
T_min = 0.928, T_max = 0.945	k = −17→17
9962 measured reflections	l = −11→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0449P)² + 0.9855P] where P = (F_o² + 2F_c²)/3
3333 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 0.39 e Å⁻³
2 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₃H₁₂N₄O₃S₂	V = 1461.6 (2) Å³
M_r = 336.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6048 (10) Å	µ = 0.38 mm⁻¹
b = 13.2273 (10) Å	T = 100 K
c = 8.9703 (7) Å	0.20 × 0.15 × 0.15 mm
β = 102.242 (1)°

Data collection top

Bruker SMART APEX diffractometer	3333 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2888 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.945	R_int = 0.028
9962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	2 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.39 e Å⁻³
3333 reflections	Δρ_min = −0.53 e Å⁻³
209 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq
S1	1.13140 (3)	0.42793 (3)	0.70269 (5)	0.01393 (12)
S2	0.34576 (3)	0.29976 (4)	0.11537 (5)	0.01750 (12)
O1	0.73961 (10)	0.47213 (10)	0.67068 (14)	0.0220 (3)
O2	0.33900 (11)	0.19520 (11)	0.07281 (17)	0.0305 (3)
O3	0.32382 (11)	0.37373 (12)	−0.00328 (15)	0.0302 (3)
C1	1.14993 (15)	0.57418 (14)	0.9320 (2)	0.0203 (4)
H1A	1.1070	0.6150	0.9888	0.030*
H1B	1.1924	0.6189	0.8799	0.030*
H1C	1.1991	0.5302	1.0029	0.030*
C2	1.07602 (14)	0.51116 (13)	0.81743 (19)	0.0155 (3)
N1	0.97011 (12)	0.51401 (11)	0.79149 (16)	0.0160 (3)
N2	0.86442 (11)	0.31764 (11)	0.42826 (16)	0.0142 (3)
N3	0.78999 (11)	0.37071 (11)	0.48923 (16)	0.0134 (3)
N4	0.26042 (13)	0.31912 (13)	0.22293 (18)	0.0214 (3)
H1	0.257 (2)	0.3836 (8)	0.242 (3)	0.038 (7)*
H2	0.277 (2)	0.2825 (17)	0.3059 (19)	0.041 (7)*
C3	0.92801 (14)	0.44919 (13)	0.67384 (18)	0.0142 (3)
C4	1.00186 (13)	0.39722 (13)	0.61098 (18)	0.0127 (3)
C5	0.96720 (13)	0.32902 (12)	0.48733 (18)	0.0137 (3)
C6	1.04567 (15)	0.26894 (15)	0.4208 (2)	0.0208 (4)
H6A	1.0069	0.2343	0.3286	0.031*
H6B	1.0811	0.2188	0.4953	0.031*
H6C	1.1006	0.3141	0.3946	0.031*
C7	0.81235 (14)	0.43424 (13)	0.61656 (19)	0.0149 (3)
C8	0.68056 (13)	0.35427 (13)	0.40510 (19)	0.0145 (3)
C9	0.65207 (15)	0.25831 (14)	0.3480 (2)	0.0221 (4)
H9	0.7026	0.2042	0.3701	0.027*
C10	0.54950 (15)	0.24169 (14)	0.2583 (2)	0.0219 (4)
H10	0.5293	0.1762	0.2187	0.026*
C11	0.47709 (13)	0.32119 (14)	0.22727 (19)	0.0161 (3)
C12	0.50573 (15)	0.41714 (14)	0.2838 (2)	0.0226 (4)
H12	0.4552	0.4711	0.2611	0.027*
C13	0.60796 (15)	0.43436 (14)	0.3732 (2)	0.0202 (4)
H13	0.6282	0.5000	0.4122	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0092 (2)	0.0149 (2)	0.0165 (2)	−0.00054 (15)	0.00014 (15)	−0.00010 (15)
S2	0.0100 (2)	0.0256 (3)	0.0150 (2)	0.00070 (16)	−0.00154 (15)	−0.00466 (16)
O1	0.0139 (6)	0.0306 (8)	0.0217 (6)	0.0011 (5)	0.0038 (5)	−0.0071 (5)
O2	0.0162 (7)	0.0324 (8)	0.0384 (8)	0.0005 (6)	−0.0042 (6)	−0.0187 (7)
O3	0.0172 (7)	0.0496 (10)	0.0211 (7)	0.0025 (6)	−0.0020 (5)	0.0096 (6)
C1	0.0185 (9)	0.0209 (9)	0.0190 (8)	−0.0030 (7)	−0.0015 (7)	−0.0042 (7)
C2	0.0165 (8)	0.0140 (8)	0.0150 (8)	−0.0001 (7)	0.0015 (6)	0.0000 (6)
N1	0.0130 (7)	0.0175 (7)	0.0164 (7)	−0.0013 (6)	0.0006 (5)	−0.0028 (6)
N2	0.0118 (7)	0.0138 (7)	0.0163 (7)	0.0014 (5)	0.0018 (5)	−0.0004 (5)
N3	0.0086 (7)	0.0146 (7)	0.0162 (7)	0.0002 (5)	0.0006 (5)	−0.0013 (5)
N4	0.0143 (7)	0.0297 (9)	0.0197 (8)	−0.0001 (7)	0.0027 (6)	−0.0038 (7)
C3	0.0146 (8)	0.0136 (8)	0.0136 (7)	0.0000 (6)	0.0012 (6)	0.0012 (6)
C4	0.0102 (8)	0.0137 (8)	0.0132 (7)	−0.0007 (6)	0.0002 (6)	0.0028 (6)
C5	0.0117 (8)	0.0132 (8)	0.0158 (7)	0.0007 (6)	0.0017 (6)	0.0016 (6)
C6	0.0137 (8)	0.0237 (9)	0.0234 (9)	0.0030 (7)	0.0007 (7)	−0.0072 (7)
C7	0.0122 (8)	0.0164 (8)	0.0155 (8)	0.0005 (6)	0.0015 (6)	0.0001 (6)
C8	0.0090 (8)	0.0173 (8)	0.0158 (8)	−0.0006 (6)	−0.0008 (6)	0.0009 (6)
C9	0.0165 (9)	0.0159 (9)	0.0299 (10)	0.0021 (7)	−0.0042 (7)	0.0008 (7)
C10	0.0167 (9)	0.0161 (9)	0.0293 (10)	−0.0017 (7)	−0.0032 (7)	−0.0036 (7)
C11	0.0096 (8)	0.0217 (9)	0.0154 (7)	−0.0001 (7)	−0.0011 (6)	−0.0003 (7)
C12	0.0161 (9)	0.0197 (9)	0.0289 (10)	0.0060 (7)	−0.0020 (8)	−0.0030 (7)
C13	0.0151 (9)	0.0152 (9)	0.0275 (9)	0.0011 (7)	−0.0021 (7)	−0.0047 (7)

Geometric parameters (Å, º) top

S1—C4	1.7142 (17)	N4—H2	0.875 (10)
S1—C2	1.7502 (17)	C3—C4	1.371 (2)
S2—O3	1.4288 (15)	C3—C7	1.453 (2)
S2—O2	1.4326 (15)	C4—C5	1.425 (2)
S2—N4	1.6105 (16)	C5—C6	1.489 (2)
S2—C11	1.7674 (17)	C6—H6A	0.9800
O1—C7	1.231 (2)	C6—H6B	0.9800
C1—C2	1.488 (2)	C6—H6C	0.9800
C1—H1A	0.9800	C8—C9	1.387 (3)
C1—H1B	0.9800	C8—C13	1.390 (2)
C1—H1C	0.9800	C9—C10	1.388 (3)
C2—N1	1.306 (2)	C9—H9	0.9500
N1—C3	1.376 (2)	C10—C11	1.382 (3)
N2—C5	1.300 (2)	C10—H10	0.9500
N2—N3	1.3746 (19)	C11—C12	1.386 (3)
N3—C7	1.398 (2)	C12—C13	1.385 (3)
N3—C8	1.441 (2)	C12—H12	0.9500
N4—H1	0.872 (10)	C13—H13	0.9500

C4—S1—C2	88.46 (8)	N2—C5—C4	120.34 (15)
O3—S2—O2	118.12 (9)	N2—C5—C6	117.64 (15)
O3—S2—N4	106.80 (9)	C4—C5—C6	122.01 (15)
O2—S2—N4	107.68 (9)	C5—C6—H6A	109.5
O3—S2—C11	108.86 (8)	C5—C6—H6B	109.5
O2—S2—C11	107.57 (8)	H6A—C6—H6B	109.5
N4—S2—C11	107.36 (8)	C5—C6—H6C	109.5
C2—C1—H1A	109.5	H6A—C6—H6C	109.5
C2—C1—H1B	109.5	H6B—C6—H6C	109.5
H1A—C1—H1B	109.5	O1—C7—N3	121.93 (15)
C2—C1—H1C	109.5	O1—C7—C3	125.48 (16)
H1A—C1—H1C	109.5	N3—C7—C3	112.59 (14)
H1B—C1—H1C	109.5	C9—C8—C13	120.93 (16)
N1—C2—C1	125.00 (16)	C9—C8—N3	118.39 (15)
N1—C2—S1	115.69 (13)	C13—C8—N3	120.53 (15)
C1—C2—S1	119.30 (13)	C8—C9—C10	119.70 (17)
C2—N1—C3	109.40 (14)	C8—C9—H9	120.2
C5—N2—N3	118.94 (14)	C10—C9—H9	120.2
N2—N3—C7	126.57 (14)	C11—C10—C9	119.39 (17)
N2—N3—C8	111.88 (13)	C11—C10—H10	120.3
C7—N3—C8	121.55 (14)	C9—C10—H10	120.3
S2—N4—H1	109.6 (17)	C10—C11—C12	120.90 (16)
S2—N4—H2	110.8 (18)	C10—C11—S2	119.45 (14)
H1—N4—H2	113 (2)	C12—C11—S2	119.64 (14)
C4—C3—N1	116.28 (15)	C13—C12—C11	120.05 (17)
C4—C3—C7	120.28 (15)	C13—C12—H12	120.0
N1—C3—C7	123.44 (15)	C11—C12—H12	120.0
C3—C4—C5	120.99 (15)	C12—C13—C8	119.02 (17)
C3—C4—S1	110.16 (12)	C12—C13—H13	120.5
C5—C4—S1	128.86 (13)	C8—C13—H13	120.5

C4—S1—C2—N1	1.29 (14)	C4—C3—C7—O1	175.26 (17)
C4—S1—C2—C1	−177.20 (15)	N1—C3—C7—O1	−4.5 (3)
C1—C2—N1—C3	177.37 (16)	C4—C3—C7—N3	−4.9 (2)
S1—C2—N1—C3	−1.03 (19)	N1—C3—C7—N3	175.35 (15)
C5—N2—N3—C7	−3.4 (2)	N2—N3—C8—C9	37.7 (2)
C5—N2—N3—C8	176.49 (15)	C7—N3—C8—C9	−142.50 (17)
C2—N1—C3—C4	0.1 (2)	N2—N3—C8—C13	−137.94 (16)
C2—N1—C3—C7	179.88 (16)	C7—N3—C8—C13	41.9 (2)
N1—C3—C4—C5	−179.24 (15)	C13—C8—C9—C10	−0.3 (3)
C7—C3—C4—C5	1.0 (2)	N3—C8—C9—C10	−175.91 (17)
N1—C3—C4—S1	0.84 (19)	C8—C9—C10—C11	0.0 (3)
C7—C3—C4—S1	−178.93 (13)	C9—C10—C11—C12	0.3 (3)
C2—S1—C4—C3	−1.12 (13)	C9—C10—C11—S2	−179.11 (15)
C2—S1—C4—C5	178.97 (16)	O3—S2—C11—C10	−129.82 (16)
N3—N2—C5—C4	−1.4 (2)	O2—S2—C11—C10	−0.72 (18)
N3—N2—C5—C6	178.80 (15)	N4—S2—C11—C10	114.92 (16)
C3—C4—C5—N2	2.5 (2)	O3—S2—C11—C12	50.76 (17)
S1—C4—C5—N2	−177.63 (13)	O2—S2—C11—C12	179.85 (15)
C3—C4—C5—C6	−177.76 (16)	N4—S2—C11—C12	−64.51 (17)
S1—C4—C5—C6	2.1 (3)	C10—C11—C12—C13	−0.3 (3)
N2—N3—C7—O1	−173.80 (15)	S2—C11—C12—C13	179.15 (15)
C8—N3—C7—O1	6.4 (3)	C11—C12—C13—C8	−0.1 (3)
N2—N3—C7—C3	6.3 (2)	C9—C8—C13—C12	0.4 (3)
C8—N3—C7—C3	−173.48 (14)	N3—C8—C13—C12	175.85 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1···O1ⁱ	0.87 (1)	2.06 (1)	2.922 (2)	169 (2)
N4—H2···O2ⁱⁱ	0.88 (1)	2.38 (2)	3.090 (2)	139 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₄O₃S₂
M_r	336.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.6048 (10), 13.2273 (10), 8.9703 (7)
β (°)	102.242 (1)
V (Å³)	1461.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.20 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.928, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	9962, 3333, 2888
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.097, 1.06
No. of reflections	3333
No. of parameters	209
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.53

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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···O1ⁱ	0.87 (1)	2.06 (1)	2.922 (2)	169 (2)
N4—H2···O2ⁱⁱ	0.88 (1)	2.38 (2)	3.090 (2)	139 (2)

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

Acknowledgements

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

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