2,7-Dimethyl-1,3-thia-zolo[4,5-d]pyridazin-4(5H)-one.

The nine-membered fused-ring system of the title pyridazine derivative, C(7)H(7)N(3)OS, is almost planar (r.m.s. deviation 0.012 Å). In the crystal, the amino H atom forms a hydrogen bond to the ketonic O atom of a neighboring mol-ecule to generate a centrosymmetric dimer.

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

C7H7N3OS

M = 181.22

Triclinic,

a = 6.9262 (4) Å

b = 7.0540 (4) Å

c = 8.8079 (6) Å

α = 71.002 (6)°

β = 75.845 (5)°

γ = 85.570 (5)°

V = 394.54 (4) Å3

Z = 2

Cu Kα radiation

μ = 3.26 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.442, T max = 0.562

2363 measured reflections

1539 independent reflections

1523 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.05

1539 reflections

115 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.30 e Å−3

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/S1600536811034192/xu5288sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034192/xu5288Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034192/xu5288Isup3.cml

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

C7H7N3OS	Z = 2
Mr = 181.22	F(000) = 188
Triclinic, P1	Dx = 1.525 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.9262 (4) Å	Cell parameters from 1965 reflections
b = 7.0540 (4) Å	θ = 6.6–74.2°
c = 8.8079 (6) Å	µ = 3.26 mm−1
α = 71.002 (6)°	T = 100 K
β = 75.845 (5)°	Prism, colorless
γ = 85.570 (5)°	0.30 × 0.25 × 0.20 mm
V = 394.54 (4) Å3

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	1539 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1523 reflections with I > 2σ(I)
Mirror	Rint = 0.012
Detector resolution: 10.4041 pixels mm-1	θmax = 74.4°, θmin = 6.6°
ω scan	h = −8→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −8→4
Tmin = 0.442, Tmax = 0.562	l = −10→10
2363 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.260P] where P = (Fo2 + 2Fc2)/3
1539 reflections	(Δ/σ)max = 0.001
115 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

	x	y	z	Uiso*/Ueq
S1	1.29210 (5)	0.13257 (5)	0.50269 (4)	0.01037 (14)
O1	0.59921 (15)	0.34439 (15)	0.67118 (13)	0.0136 (2)
N1	0.97795 (18)	0.13725 (17)	0.73210 (15)	0.0114 (3)
N2	0.74300 (18)	0.42456 (18)	0.39677 (15)	0.0112 (3)
H2	0.636 (3)	0.490 (3)	0.371 (3)	0.027 (5)*
N3	0.88967 (18)	0.43408 (18)	0.25907 (15)	0.0121 (3)
C1	1.2623 (2)	−0.0391 (2)	0.84407 (19)	0.0157 (3)
H1A	1.1669	−0.0660	0.9512	0.024*
H1B	1.3732	0.0410	0.8415	0.024*
H1C	1.3131	−0.1663	0.8277	0.024*
C2	1.1611 (2)	0.0736 (2)	0.70979 (18)	0.0118 (3)
C3	0.9338 (2)	0.2388 (2)	0.58191 (17)	0.0103 (3)
C4	0.7459 (2)	0.3356 (2)	0.56003 (18)	0.0107 (3)
C5	1.0839 (2)	0.2502 (2)	0.44375 (18)	0.0101 (3)
C6	1.0596 (2)	0.3495 (2)	0.27985 (18)	0.0111 (3)
C7	1.2245 (2)	0.3608 (2)	0.13145 (18)	0.0167 (3)
H7A	1.1756	0.4244	0.0312	0.025*
H7B	1.2713	0.2252	0.1345	0.025*
H7C	1.3346	0.4401	0.1314	0.025*

	U11	U22	U33	U12	U13	U23
S1	0.0081 (2)	0.0092 (2)	0.0123 (2)	0.00189 (13)	−0.00196 (13)	−0.00205 (14)
O1	0.0089 (5)	0.0137 (5)	0.0156 (5)	0.0007 (4)	0.0001 (4)	−0.0034 (4)
N1	0.0113 (6)	0.0082 (6)	0.0136 (6)	−0.0004 (4)	−0.0028 (5)	−0.0019 (5)
N2	0.0081 (6)	0.0104 (6)	0.0140 (6)	0.0020 (5)	−0.0022 (5)	−0.0032 (5)
N3	0.0120 (6)	0.0103 (6)	0.0130 (6)	0.0000 (5)	−0.0018 (5)	−0.0029 (5)
C1	0.0147 (7)	0.0150 (7)	0.0155 (7)	0.0025 (6)	−0.0051 (6)	−0.0015 (6)
C2	0.0124 (7)	0.0076 (6)	0.0142 (7)	−0.0016 (5)	−0.0020 (5)	−0.0021 (5)
C3	0.0103 (7)	0.0057 (6)	0.0137 (7)	−0.0016 (5)	−0.0019 (5)	−0.0016 (5)
C4	0.0103 (7)	0.0057 (6)	0.0157 (7)	−0.0021 (5)	−0.0030 (5)	−0.0025 (5)
C5	0.0095 (6)	0.0060 (6)	0.0151 (7)	0.0002 (5)	−0.0034 (5)	−0.0034 (5)
C6	0.0122 (7)	0.0078 (6)	0.0127 (7)	−0.0011 (5)	−0.0026 (5)	−0.0022 (5)
C7	0.0151 (7)	0.0191 (8)	0.0127 (7)	0.0022 (6)	−0.0017 (6)	−0.0022 (6)

S1—C5	1.7141 (14)	C1—H1A	0.9800
S1—C2	1.7546 (15)	C1—H1B	0.9800
O1—C4	1.2404 (18)	C1—H1C	0.9800
N1—C2	1.3025 (19)	C3—C5	1.378 (2)
N1—C3	1.3797 (18)	C3—C4	1.4480 (19)
N2—N3	1.3647 (17)	C5—C6	1.430 (2)
N2—C4	1.3736 (19)	C6—C7	1.4953 (19)
N2—H2	0.88 (2)	C7—H7A	0.9800
N3—C6	1.3037 (19)	C7—H7B	0.9800
C1—C2	1.493 (2)	C7—H7C	0.9800
C5—S1—C2	89.25 (7)	N1—C3—C4	125.15 (13)
C2—N1—C3	110.07 (12)	O1—C4—N2	120.86 (13)
N3—N2—C4	129.17 (12)	O1—C4—C3	126.43 (13)
N3—N2—H2	111.4 (14)	N2—C4—C3	112.70 (12)
C4—N2—H2	119.3 (14)	C3—C5—C6	122.57 (13)
C6—N3—N2	117.76 (12)	C3—C5—S1	109.49 (11)
C2—C1—H1A	109.5	C6—C5—S1	127.94 (11)
C2—C1—H1B	109.5	N3—C6—C5	119.21 (13)
H1A—C1—H1B	109.5	N3—C6—C7	119.01 (13)
C2—C1—H1C	109.5	C5—C6—C7	121.77 (13)
H1A—C1—H1C	109.5	C6—C7—H7A	109.5
H1B—C1—H1C	109.5	C6—C7—H7B	109.5
N1—C2—C1	125.25 (13)	H7A—C7—H7B	109.5
N1—C2—S1	114.91 (11)	C6—C7—H7C	109.5
C1—C2—S1	119.83 (11)	H7A—C7—H7C	109.5
C5—C3—N1	116.28 (12)	H7B—C7—H7C	109.5
C5—C3—C4	118.56 (13)
C4—N2—N3—C6	−0.4 (2)	N1—C3—C5—C6	179.58 (12)
C3—N1—C2—C1	178.83 (13)	C4—C3—C5—C6	−1.6 (2)
C3—N1—C2—S1	−0.33 (15)	N1—C3—C5—S1	−0.99 (16)
C5—S1—C2—N1	−0.18 (11)	C4—C3—C5—S1	177.81 (10)
C5—S1—C2—C1	−179.39 (12)	C2—S1—C5—C3	0.63 (10)
C2—N1—C3—C5	0.86 (17)	C2—S1—C5—C6	−179.99 (13)
C2—N1—C3—C4	−177.85 (12)	N2—N3—C6—C5	0.55 (19)
N3—N2—C4—O1	178.56 (12)	N2—N3—C6—C7	−178.84 (12)
N3—N2—C4—C3	−0.7 (2)	C3—C5—C6—N3	0.5 (2)
C5—C3—C4—O1	−177.59 (13)	S1—C5—C6—N3	−178.85 (10)
N1—C3—C4—O1	1.1 (2)	C3—C5—C6—C7	179.84 (13)
C5—C3—C4—N2	1.63 (18)	S1—C5—C6—C7	0.5 (2)
N1—C3—C4—N2	−179.69 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.88 (2)	1.97 (2)	2.845 (2)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.88 (2)	1.97 (2)	2.845 (2)	173 (2)

Symmetry code: (i) .