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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 [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.129
Data-to-parameter ratio = 16.5
Details
Open access

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

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-H...O and C-H...N 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[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 et al. (2011[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.]); Park et al. (2007[Park, J. S., Yu, K. A., Kang, T. H., Kim, S. & Suh, Y. G. (2007). Bioorg. Med. Chem. Lett. 17, 3486-3490.]); Plescia et al. (2010[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 et al. (2009[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.]). For related structures, see: Gerpe et al. (2007[Gerpe, A., Piro, O. E., Cerecetto, H. & Gonzales, M. (2007). J. Mol. Struct. 871, 98-107.]); Özel Güven et al. (2008a[Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008a). Acta Cryst. E64, o1358.],b[Özel Güven, Ö., Tahtaci, H., Coles, S. J. & Hökelek, T. (2008b). Acta Cryst. E64, o1604.]); Raffa et al. (2009[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.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N2O

  • Mr = 236.27

  • Monoclinic, P 21 /n

  • a = 9.4408 (3) Å

  • b = 17.9636 (5) Å

  • c = 13.9415 (4) Å

  • [beta] = 99.247 (4)°

  • V = 2333.62 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.084

  • 3 standard reflections every 2 min intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.129

  • S = 1.02

  • 5349 reflections

  • 325 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
C6A-H6A...O1Bi 0.93 2.53 3.418 (2) 159
C8A-H81...N2Aii 0.97 2.57 3.519 (3) 164
C8A-H82...O1Biii 0.97 2.41 3.176 (2) 135
C9B-H9B...Cg1iv 0.93 2.86 3.460 (2) 123
C3B-H3B...Cg2v 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[Rigaku (2011). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [ISI] [CrossRef] [ChemPort] [details]
Gerpe, A., Piro, O. E., Cerecetto, H. & Gonzales, M. (2007). J. Mol. Struct. 871, 98-107.  [ISI] [CSD] [CrossRef] [ChemPort]
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.  [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [PubMed]
Özel Güven, Ö., Erdogan, T., Coles, S. J. & Hökelek, T. (2008a). Acta Cryst. E64, o1358.  [CSD] [CrossRef] [details]
Özel Güven, Ö., Tahtaci, H., Coles, S. J. & Hökelek, T. (2008b). Acta Cryst. E64, o1604.  [CSD] [CrossRef] [details]
Park, J. S., Yu, K. A., Kang, T. H., Kim, S. & Suh, Y. G. (2007). Bioorg. Med. Chem. Lett. 17, 3486-3490.  [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Rigaku (2011). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o184  [ doi:10.1107/S1600536812051811 ]

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