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Volume 69 
Part 2 
Page o243  
February 2013  

Received 30 November 2012
Accepted 10 January 2013
Online 16 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.151
Data-to-parameter ratio = 18.2
Details
Open access

rac-1-[6-Hydroxy-4-(4-methoxyphenyl)-3,6-dimethyl-4,5,6,7-tetrahydro-2H-indazol-5-yl]ethanone

aVladimir State University, Qor'ky St 87, 600000 Vladimir, Russian Federation, and bBaku State University, Z. Khalilov St 23, AZ-1148 Baku, Azerbaijan
Correspondence e-mail: Naralab7@gmail.com

The title compound, C18H22N2O3, represents a (4S,5R,6S)-stereoisomer, crystallizing as a racemate in a centrosymmetric space group. The six-membered aliphatic ring adopts a half-chair conformation, with the hydroxy- and acetyl-substituted C atoms deviating by 0.458 (2) and -0.366 (2) Å, respectively, from the plane defined by other four ring atoms. The pyrazole ring is essentially planar [r.m.s deviation = 0.004 (2) Å]. In the crystal, the molecules are linked into chains along the b axis by N-H...N hydrogen bonds. The chains are linked by O-H...N hydrogen bonds into layers parallel to the bc plane.

Related literature

For background to the use of [beta]-cycloketols as synthons in the synthesis of pyrazoles, see: Pramula et al. (1985[Pramula, B., Rajanarender, E., Shoolery, J. N. & Krishna, M. (1985). Indian J. Chem. Sect. B, 24, 1255-1258.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C18H22N2O3

  • Mr = 314.38

  • Monoclinic, P 21 /c

  • a = 18.3693 (14) Å

  • b = 5.6971 (4) Å

  • c = 16.3049 (12) Å

  • [beta] = 109.526 (1)°

  • V = 1608.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.974, Tmax = 0.982

  • 17994 measured reflections

  • 4015 independent reflections

  • 2740 reflections with I > 2[sigma](I)

  • Rint = 0.053

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

  • wR(F2) = 0.151

  • S = 1.00

  • 4015 reflections

  • 220 parameters

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O...N2i 0.81 (3) 2.15 (3) 2.948 (2) 168 (2)
N1-H1N...N2ii 0.87 (2) 2.27 (2) 3.093 (2) 157 (2)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2089 ).


Acknowledgements

We thank Baku State University and Vladimir State University for supporting this study.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Pramula, B., Rajanarender, E., Shoolery, J. N. & Krishna, M. (1985). Indian J. Chem. Sect. B, 24, 1255-1258.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o243  [ doi:10.1107/S1600536813000937 ]

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