The crystal structure of 3-chloro-2-(4-methyl-phenyl)-2H-pyrazolo-[3,4-b]quinoline

Haliwana B V Sowmya; Tholappanavara H Suresha Kumara; Jerry P Jasinski; Sean P Millikan; Hemmige S Yathirajan; Christopher Glidewell

doi:10.1107/S205698901500818X

The crystal structure of 3-chloro-2-(4-methyl-phenyl)-2H-pyrazolo-[3,4-b]quinoline

Acta Crystallogr E Crystallogr Commun. 2015 Apr 30;71(Pt 5):567-70. doi: 10.1107/S205698901500818X. eCollection 2015 May 1.

Authors

Haliwana B V Sowmya¹, Tholappanavara H Suresha Kumara², Jerry P Jasinski³, Sean P Millikan³, Hemmige S Yathirajan⁴, Christopher Glidewell⁵

Affiliations

¹ PG Department of Chemistry, Jain University, 52 Bellary Road, Hebbal, Bangalore 560 024, India.
² University B.D.T. College of Engineering, (a Constituent College of VTU, Belgaum), Davanagere 577 004, India.
³ Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA.
⁴ Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India.
⁵ School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland.

Abstract

In the mol-ecule of 3-chloro-2-(4-methyl-phen-yl)-2H-pyrazolo-[3,4-b]quinoline, C17H12ClN3, (I), the dihedral angle between the planes of the pyrazole ring and the methyl-ated phenyl ring is 54.25 (9)°. The bond distances in the fused tricyclic system provide evidence for 10-π delocalization in the pyrazolo-pyridine portion of the mol-ecule, with diene character in the fused carbocyclic ring. In the crystal, mol-ecules of (I) are linked by two independent C-H⋯N hydrogen bonds, forming sheets containing centrosymmetric R 2 (2)(16) and R 6 (4)(28) rings, and these sheets are all linked together by π-π stacking inter-actions with a ring-centroid separation of 3.5891 (9) Å.

Keywords: crystal structure; hydrogen bonding; pyrazoloquinoline; π–π stacking interactions.