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Volume 64 
Part 10 
Page o1924  
October 2008  

Received 28 August 2008
Accepted 6 September 2008
Online 13 September 2008

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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.107
Data-to-parameter ratio = 16.1
Details
Open access

5-Methyl-2-phenyl-2H-pyrazol-3-ol

Qiang Wang,a Yi Zhang,a Rong Wang,a Yi-Lin Yanga* and Feng Zhib*

aDepartment of Neurosurgery, Third Affiliated Hospital of Soochow University, Changzhou 213003, People's Republic of China, and bLaboratory of Neuronal Injury and Protection, Third Affiliated Hospital of Soochow University, Changzhou 213003, People's Republic of China
Correspondence e-mail: czfph@yahoo.com.cn, danielzhif@yahoo.com.cn

The title compound, C10H10N2O, known as Edaravone (MCI-186), was crystallized from methanol. The two independent molecules in the asymmetric unit are linked through an O-H...O hydrogen bond. One molecule adopts a ketone form, while the other adopts an enol form. In the crystal structure, molecules are linked through intermolecular N-H...O hydrogen bonds, forming chains running along the b axis.

Related literature

For background to the compound, see: Watanabe et al. (1994[Watanabe, T., Yuki, S., Egawa, M. & Nishi, H. (1994). J. Pharmacol. Exp. Ther. 268, 1597-1604.]); The Edaravone Acute Infarction Study Group (2003[The Edaravone Acute Infarction Study Group (2003). Cerebrovasc. Dis. 15, 222-229.]). For bond-length data, see: Allen et al. (1987[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.]).[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]

[Scheme 1]

Experimental

Crystal data

  • C10H10N2O

  • Mr = 174.20

  • Monoclinic, P 21 /c

  • a = 10.336 (2) Å

  • b = 11.154 (2) Å

  • c = 15.863 (3) Å

  • [beta] = 95.157 (3)°

  • V = 1821.4 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 (2) K

  • 0.23 × 0.23 × 0.20 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.981, Tmax = 0.983

  • 10551 measured reflections

  • 3923 independent reflections

  • 2894 reflections with I > 2[sigma](I)

  • Rint = 0.025
Refinement

  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.106

  • S = 1.04

  • 3923 reflections

  • 243 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...N4i 0.907 (9) 1.904 (10) 2.7999 (17) 169.4 (17)
O2-H2B...O1 0.870 (9) 1.618 (10) 2.4813 (15) 170.9 (19)
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2259 ).

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.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
The Edaravone Acute Infarction Study Group (2003). Cerebrovasc. Dis. 15, 222-229.  [CrossRef] [PubMed]
Watanabe, T., Yuki, S., Egawa, M. & Nishi, H. (1994). J. Pharmacol. Exp. Ther. 268, 1597-1604.  [ChemPort] [PubMed]

Acta Cryst (2008). E64, o1924  [ doi:10.1107/S1600536808028559 ]

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