2-(2H-Indazol-2-yl)-1-phenyl­ethanone

Özel Güven, Ö.; Türk, G.; Adler, P.D.F.; Coles, S.J.; Hökelek, T.

doi:10.1107/S1600536812051811

Volume 69
Part 2
Page o184
February 2013

Received 3 December 2012
Accepted 24 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.057
wR = 0.129
Data-to-parameter ratio = 16.5
Details

2-(2H-Indazol-2-yl)-1-phenylethanone

Özden Özel Güven,^a Gökhan Türk,^a Philip D. F. Adler,^b Simon J. Coles ^b and Tuncer Hökelek ^c ^*

^aDepartment of Chemistry, Bülent Ecevit University, 67100 Zonguldak, Turkey,^bDepartment of Chemistry, Southampton University, SO17 1BJ Southampton, England, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

The asymmetric unit of the title compound, C₁₅H₁₂N₂O, contains two independent molecules with different conformations, the phenyl ring and indazole mean plane in the two molecules forming dihedral angles of 50.82 (5) and 89.29 (6)°. In the crystal, weak C-HO and C-HN hydrogen bonds and C-H [pi] interactions consolidate the packing.

Related literature

For general background to the biological activity of indazole derivatives, see: Lebouvier et al. (2007); Maggio et al. (2011); Park et al. (2007); Plescia et al. (2010); Raffa et al. (2009). For related structures, see: Gerpe et al. (2007); Özel Güven et al. (2008a,b); Raffa et al. (2009).

Experimental

Crystal data

C₁₅H₁₂N₂O
M_r = 236.27
Monoclinic, P 2₁ /n
a = 9.4408 (3) Å
b = 17.9636 (5) Å
c = 13.9415 (4) Å
= 99.247 (4)°
V = 2333.62 (12) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn724+ diffractometer
23377 measured reflections
5349 independent reflections
3346 reflections with I > 2(I)
R_int = 0.084
3 standard reflections every 2 min intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.129
S = 1.02
5349 reflections
325 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1A/N2A/C9A/C10A/C15A and C10B-C15B rings, respectively.

D-HA	D-H	HA	DA	D-HA
C6A-H6AO1Bⁱ	0.93	2.53	3.418 (2)	159
C8A-H81N2Aⁱⁱ	0.97	2.57	3.519 (3)	164
C8A-H82O1Bⁱⁱⁱ	0.97	2.41	3.176 (2)	135
C9B-H9BCg1^iv	0.93	2.86	3.460 (2)	123
C3B-H3BCg2^v	0.93	2.60	3.433 (2)	149
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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, 2012); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5372 ).

Acknowledgements

The authors acknowledge the Zonguldak Karaelmas University Research Fund (project No. 2012-10-03-12).

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gerpe, A., Piro, O. E., Cerecetto, H. & Gonzales, M. (2007). J. Mol. Struct. 871, 98-107.
Lebouvier, N., Pagniez, F., Duflos, M., Le Pape, P., Na, Y. M., Le Baut, G. & Le Borgne, M. (2007). Bioorg. Med. Chem. Lett. 17, 3686-3689.
Maggio, B., Raimondi, M. V., Raffa, D., Plescia, F., Cascioferro, S., Plescia, S., Tolomeo, M., Di Cristina, A., Pipitone, R. M., Grimaudo, S. & Daidone, G. (2011). Eur. J. Med. Chem. 46, 168-174.
Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008a). Acta Cryst. E64, o1358.
Özel Güven, Ö., Tahtaci, H., Coles, S. J. & Hökelek, T. (2008b). Acta Cryst. E64, o1604.
Park, J. S., Yu, K. A., Kang, T. H., Kim, S. & Suh, Y. G. (2007). Bioorg. Med. Chem. Lett. 17, 3486-3490.
Plescia, S., Raffa, D., Plescia, F., Casula, G., Maggio, B., Daidone, G., Raimondi, M. V., Cusimano, M. G., Bombieri, G. & Meneghetti, F. (2010). Arkivoc, pp. 163-177.
Raffa, D., Maggio, B., Cascioferro, S., Raimondi, M. V., Schillaci, D., Gallo, G., Daidone, G., Plescia, S., Meneghetti, F., Bombieri, G., Di Cristina, A., Pipitone, R. M., Grimaudo, S. & Tolomeo, M. (2009). Eur. J. Med. Chem. 44, 165-178.
Rigaku (2011). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds