Ethyl 3-methyl-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-d]pyridazine-2-carboxyl­ate

Chen, S.-Q.; Jiang, K.; Wang, S.-F.

doi:10.1107/S1600536809055081

Volume 66
Part 2
Page o259
February 2010

Received 18 December 2009
Accepted 22 December 2009
Online 9 January 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.044
wR = 0.120
Data-to-parameter ratio = 13.1
Details

Ethyl 3-methyl-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-d]pyridazine-2-carboxylate

Shi-Quan Chen,^a Kai Jiang ^b and Shi-Fan Wang ^c,^a ^*

^aKey Laboratory of Tropical Biological Resources of the Ministry of Education, Hainan University, Haikou 570228, People's Republic of China,^bExperimental Teaching Center of Marine Biology, Hainan University, Haikou 570228, People's Republic of China, and ^cSchool of Ocean, Hainan University, Haikou 570228, People's Republic of China
Correspondence e-mail: wangsf777@gmail.com

The title compound, C₁₀H₁₁N₃O₃, was synthesized by the reaction of 3,5-bis(ethoxycarbonyl)-2-formyl-4-methyl-1H-pyrrole and hydrazine hydrate. The angle between the pyrrole ring and the pyridazinone ring is 0.93 (9)°. In the crystal, intermolecular N-HO and N-HN hydrogen-bond interactions link the molecules into a two-dimensional network.

Related literature

For the biological activity of pyrrolopyridazine compounds, see: Chen et al. (2006); Hu et al. (2004); Swamy et al. (2005). For bond-length data, see Allen et al. (1987).

Experimental

Crystal data

C₁₀H₁₁N₃O₃
M_r = 221.22
Monoclinic, P 2₁ /c
a = 8.0030 (16) Å
b = 9.774 (2) Å
c = 13.370 (3) Å
= 90.17 (3)°
V = 1045.8 (4) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 295 K
0.40 × 0.26 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.959, T_max = 0.994
6834 measured reflections
2045 independent reflections
1676 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.120
S = 1.06
2045 reflections
156 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.27 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3O1ⁱ	0.90 (3)	1.90 (3)	2.804 (2)	175 (2)
N1-H1N2ⁱⁱ	0.86 (2)	2.08 (2)	2.925 (2)	166.2 (17)
Symmetry codes: (i) -x, -y, -z+2; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker 2002); cell refinement: SAINT (Bruker 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2715 ).

Acknowledgements

This research was supported financially by the National Natural Science Foundation of China (30660215).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Swamy, K. M. K., Park, M. S., Han, S. J., Kim, S. K., Kim, J. H., Lee, C., Bang, H., Kim, Y., Kim, S.-J. & Yoon, J. (2005). Tetrahedron, 61, 10227-10234.

organic compounds