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

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

doi:10.1107/S1600536811034192

Volume 67
Part 9
Page o2467
September 2011

Received 6 August 2011
Accepted 20 August 2011
Online 27 August 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.029
wR = 0.080
Data-to-parameter ratio = 13.4
Details

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

Abdulrahman O. Al-Youbi,^a Abdullah M. Asiri,^a Hassan M. Faidallah ^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

The nine-membered fused-ring system of the title pyridazine derivative, C₇H₇N₃OS, 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 molecule 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_r = 181.22
Triclinic, $[P \overline 1]$
a = 6.9262 (4) Å
b = 7.0540 (4) Å
c = 8.8079 (6) Å
= 71.002 (6)°
= 75.845 (5)°
= 85.570 (5)°
V = 394.54 (4) Å³
Z = 2
Cu K radiation
= 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 > 2(I)
R_int = 0.012

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.080
S = 1.05
1539 reflections
115 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.41 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	0.88 (2)	1.97 (2)	2.845 (2)	173 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: XU5288 ).

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.
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Faid-Allah, H. S., Khan, K. A. & Makki, M. S. (2011). J. Chin. Chem. Soc. 58, 191-198.
Makki, M. S. & Faid-Allah, H. S. (1996). J. Chin. Chem. Soc. 43, 433-438.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds