2-(4-Methyl­phen­yl)-2H-indazole

Zhou, X.; Qin, X.; Zhang, J.

doi:10.1107/S1600536810038948

Volume 66
Part 11
Page o2732
November 2010

Received 23 September 2010
Accepted 29 September 2010
Online 9 October 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.140
Data-to-parameter ratio = 13.2
Details

2-(4-Methylphenyl)-2H-indazole

Xingqin Zhou,^a ^* Xiaofen Qin ^a and Jiankang Zhang ^a

^aKey Laboratory of Nuclear Medicine, Ministry of Health, Jiangsu Key Laboratory of Molecular Nuclear Medicine, Jiangsu Institute of Nuclear Medicine, Wuxi, Jiangsu 214063, People's Republic of China
Correspondence e-mail: xingqin118@126.com

The title compound, C₁₄H₁₂N₂, was synthesized by the reaction of 4-methyl-N-(2-nitrobenzyl)aniline with tin(II) chloride dihydrate in ethanol at 313 K. The indazole ring system is almost planar with a dihedral angle of 1.58 (10)° between the rings, whereas the plane of the attached p-tolyl substituent shows a dihedral angle of 46.26 (5)° with respect to the indazole core.

Related literature

For the pharmaceutical properties of indazole derivatives, see: Bistochi et al. (1981); Cerecetto et al. (2005); Corsi et al. (1976); Keppler & Hartmann (1994); Picciola et al. (1981); Rodgers et al. (1996); Sun et al. (1997); Ykeda et al. (1979). For synthetic procedures for indazoles, see: Stadlbauer (2002).

Experimental

Crystal data

C₁₄H₁₂N₂
M_r = 208.26
Monoclinic, P 2₁ /n
a = 12.539 (4) Å
b = 6.029 (2) Å
c = 14.401 (5) Å
= 93.636 (5)°
V = 1086.4 (6) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 298 K
0.48 × 0.34 × 0.31 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.969, T_max = 0.980
5372 measured reflections
1915 independent reflections
1236 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.140
S = 1.03
1911 reflections
145 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.26 e Å^-3

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2233 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (30770602) and the Natural Science Foundation of Jiangsu Province, China (BK2010157).

References

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Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
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