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

Potekhin, K.A.; Askerov, R.K.; Hajiyeva, K.E.; Gadirova, N.A.; Nazarov, S.I.

doi:10.1107/S1600536813000937

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 (C-C) = 0.003 Å
R = 0.057
wR = 0.151
Data-to-parameter ratio = 18.2
Details

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

Konstantin A. Potekhin,^a Rizvan K. Askerov,^b Kushvar E. Hajiyeva,^b Narmina A. Gadirova ^b ^* and Shahkaram I. Nazarov ^b

^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-HN hydrogen bonds. The chains are linked by O-HN 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). For hydrogen-bond motifs, see: Bernstein et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₈H₂₂N₂O₃
M_r = 314.38
Monoclinic, P 2₁ /c
a = 18.3693 (14) Å
b = 5.6971 (4) Å
c = 16.3049 (12) Å
= 109.526 (1)°
V = 1608.2 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.974, T_max = 0.982
17994 measured reflections
4015 independent reflections
2740 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(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
_max = 0.28 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1ON2ⁱ	0.81 (3)	2.15 (3)	2.948 (2)	168 (2)
N1-H1NN2ⁱⁱ	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); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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.
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.
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.

organic compounds