4-(4-Bromo­phen­yl)-4,5,6,7-tetra­hydro-3-methyl-6-oxo-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile ethanol solvate

Fan, X.-S.; Li, X.-Y.; Wang, X.; Li, D.-F.; Zhang, X.-Y.

doi:10.1107/S1600536808028638

Volume 64
Part 10
Page o1925
October 2008

Received 1 September 2008
Accepted 7 September 2008
Online 13 September 2008

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R = 0.047
wR = 0.122
Data-to-parameter ratio = 14.9
Details

4-(4-Bromophenyl)-4,5,6,7-tetrahydro-3-methyl-6-oxo-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile ethanol solvate

Xue-Sen Fan,^a ^* Xiao-Yan Li,^a Xia Wang,^a Dong-Fang Li ^a and Xin-Ying Zhang ^a

^aSchool of Chemistry and Environmental Sciences, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, Xinxiang, Henan 453007, People's Republic of China
Correspondence e-mail: xuesen.fan@yahoo.com

In the structure of the title compound, C₂₀H₁₅BrN₄O·C₂H₆O, the hydrogenated pyridinone ring adopts an envelope conformation. The dihedral angle between the bromo-substituted phenyl ring and the pyrazole ring is 79.6 (1)°, and that between the non-substituted phenyl ring and the pyrazole ring is 51.2 (1)°. In the crystal structure, molecules are linked via intermolecular N-HO and O-HN hydrogen bonds. A short intermolecular NBr contact [3.213 (4) Å] is present in the crystal structure.

Related literature

For general background, see: Falcó et al. (2005); Kung & Wager (2007).

Experimental

Crystal data

C₂₀H₁₅BrN₄O·C₂H₆O
M_r = 453.34
Monoclinic, P 2₁ /c
a = 21.871 (9) Å
b = 9.209 (4) Å
c = 10.552 (5) Å
= 90.370 (5)°
V = 2125.4 (15) Å³
Z = 4
Mo K radiation
= 1.96 mm^-1
T = 295 (2) K
0.31 × 0.24 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997) T_min = 0.586, T_max = 0.770
10428 measured reflections
3947 independent reflections
2414 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.121
S = 1.01
3947 reflections
265 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.51 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2N1ⁱ	0.82	2.06	2.874 (4)	171
N3-H3DO2	0.97	1.84	2.786 (3)	166
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2452 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20772025) and the Program for Science and Technology Innovation Talents in Universities of Henan Province (No. 2008HASTIT006).

References

Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Falcó, J. L., Lloveras, M., Buira, I., Teixidó, J., Borrell, J. I., Méndez, E., Terencio, J., Palomer, A. & Guglietta, A. (2005). Eur. J. Med. Chem. 40, 1179-1187.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Kung, D. W. & Wager, T. T. (2007). US Patent 7 300 944.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds