1-Phenyl-6,7,8,9-hexa­hydro-1H,5H-cyclo­hepta­[1′,2′:2,3]pyrido[6,5-c]pyrazol-4-amine: a new tacrine analogue

Zhang, L.; Shi, D.; Li, J.; Zhang, L.; Fan, Y.

doi:10.1107/S1600536808013366

Volume 64
Part 6
Page o1056
June 2008

Received 14 April 2008
Accepted 6 May 2008
Online 10 May 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.064
wR = 0.163
Data-to-parameter ratio = 13.6
Details

1-Phenyl-6,7,8,9-hexahydro-1H,5H-cyclohepta[1',2':2,3]pyrido[6,5-c]pyrazol-4-amine: a new tacrine analogue

Lijun Zhang,^a Daxin Shi,^a Jiarong Li,^a ^* Ling Zhang ^a and Yanqiu Fan ^a

^aSchool of Chemical Engineering and the Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
Correspondence e-mail: cdlijun@bit.edu.cn

The title compound, C₁₇H₁₈N₄, contains a pyrazolopyridine system fused with a seven-membered carbocyclic ring. The pyrazole ring is coplanar with the pyridine ring, while the phenyl ring is twisted by a dihedral angle of 14.38 (14)° with respect to the pyridine ring. The seven-membered ring displays a chair conformation. The packing is stabilized by N-HN hydrogen bonds and N-H [pi] (arene) interactions.

Related literature

For related literature, see: Gracon et al. (1998); Haviv et al. (2005); Kelley et al. (1988); Kim et al. (1996); Lin et al. (2007); Stachlewitz et al. (1997); Zocchi et al. (1996); Erast et al. (1987).

Experimental

Crystal data

C₁₇H₁₈N₄
M_r = 278.35
Monoclinic, P 2₁ /a
a = 13.694 (13) Å
b = 6.888 (6) Å
c = 16.929 (16) Å
= 112.417 (12)°
V = 1476 (2) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 (2) K
0.24 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (Jacobson, 1998) T_min = 0.982, T_max = 0.992
10708 measured reflections
2593 independent reflections
2004 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.064
wR(F²) = 0.162
S = 1.13
2593 reflections
190 parameters
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1BN4ⁱ	0.86	2.28	3.139 (4)	175
N1-H1ACg1ⁱⁱ	0.86	2.84	3.608 (4)	150
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z]$ ; (ii) $[x-{\script{3\over 2}}, -y-{\script{1\over 2}}, z]$ . Cg1 is the centroid of the benzene ring.

Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2339 ).

Acknowledgements

We thank Beijing Institute of Technology for financial support and Naikai University for the X-ray diffraction analysis.

References

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
Erast, B., Bend, Z. & Norbert, M. (1987). German Patent DE 3 604 569.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gracon, S. I., Knapp, M. J., Berghoff, W. G., Pierce, M., DeJong, R., Lobbestael, S. J., Symons, J., Dombey, S. L., Luscombe, F. A. & Kraemer, D. (1998). Alzheimer Dis. Assoc. Disord. 12, 93-101.
Haviv, H., Wong, D. M., Greenblatt, H. M., Carlier, P. R., Han, Y. F., Pang, Y. P., Silman, I. & Sussman, J. L. (2005). J. Am. Chem. Soc. 127, 11029-11036.
Jacobson, R. (1998). Private communication to the Rigaku Corporation, Tokyo, Japan.
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Rigaku (2004). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Stachlewitz, R. F., Arteel, G. E., Raleigh, J. A., Connor, H. D., Mason, R. P. & Thurman, R. G. J. (1997). J. Pharmacol. Exp. Ther. 282, 1591-1599.
Zocchi, C., Ongini, E., Conti, A., Monopoli, A., Negretti, A., Baraldi, P. G. & Dionisotti, S. (1996). J. Pharmacol. Exp. Ther. 276, 398-404.

organic compounds