3-(4-Pyrid­yl)-4,5-dihydro-1H-benzo[g]indazole

Xiao, X.; Zhang, Y.-Q.; Xue, S.-F.; Zhu, Q.-J.; Tao, Z.

doi:10.1107/S1600536808038944

Volume 64
Part 12
Page o2449
December 2008

Received 2 November 2008
Accepted 20 November 2008
Online 26 November 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.130
Data-to-parameter ratio = 12.9
Details

3-(4-Pyridyl)-4,5-dihydro-1H-benzo[g]indazole

Xin Xiao,^a Yun-Qiang Zhang,^a Sai-Feng Xue,^a Qian-Jiang Zhu ^a ^* and Zhu Tao ^b

^aKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China, and ^bInstitute of Applied Chemistry, Guizhou University, Guiyang 550025, People's Republic of China
Correspondence e-mail: gyhxxiaoxin@163.com

In the molecular structure of the title compound, C₁₆H₁₃N₃, the cyclohexa-1,3-diene ring displays a screw-boat conformation and the pyridine ring is twisted by a dihedral angle of 29.13 (9)° with respect to the pyrazole ring. Molecules are linked into a supramolecular structure by N-HN hydrogen bonding.

Related literature

For general background to indazole derivatives and their pharmacological properties, see: Bistochi et al. (1981); Keppler & Hartmann (1994); Sun et al. (1997); Gomtsyan et al. (2008).

Experimental

Crystal data

C₁₆H₁₃N₃
M_r = 247.29
Orthorhombic, P b c a
a = 15.306 (2) Å
b = 8.8368 (13) Å
c = 18.543 (3) Å
V = 2508.1 (6) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 293 (2) K
0.22 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
24926 measured reflections
2217 independent reflections
1978 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.130
S = 1.08
2217 reflections
172 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2N3ⁱ	0.86	2.17	2.895 (2)	141
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2463 ).

Acknowledgements

The authors gratefully acknowledge the Natural Science Foundation of China (No. 20767001), the International Collaborative Project of Guizhou Province, the Governor Foundation of Guizhou Province and the Natural Science Youth Foundation of Guizhou University (No. 2007-005) for financial support.

References

Bistochi, G. A., De Meo, G., Pedini, M., Ricci, A., Brouilhet, H., Bucherie, S., Rabaud, M. & Jacquignon, P. (1981). Farmaco Ed. Sci. 36, 315-333.
Bruker (2002). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gomtsyan, A., Bayburt, E. K., Schmidt, R. G., Surowy, C. S., Honore, P., Marsh, K. C., Hannick, S. M., McDonald, H. A., Wetter, J. M., Sullivan, J. P., Jarvis, M. F., Faltynek, C. R. & Lee, C. H. (2008). J. Med. Chem. 51, 392-395.
Keppler, B. K. & Hartmann, M. (1994). Met. Based Drugs. 1, 145-149.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sun, J. H., Teleha, C. A., Yan, J. S., Rodgers, J. D. & Nugiel, D. A. (1997). J. Org. Chem. 62, 5627-5629.

organic compounds