Research Article: 5-Chloro-3,6-dimethyl-1-phenyl-1H,4H-pyrano[2,3-c]pyrazol-4-one

Date Published: July 01, 2012

Publisher: International Union of Crystallography

Author(s): Abdullah M. Asiri, Hassan M. Faidallah, Khalid A. Alamry, Seik Weng Ng, Edward R. T. Tiekink.


In the title compound, C14H11ClN2O2, two independent mol­ecules (A and B) comprise the asymmetric unit with the main difference between them being the relative orientation of the pendent phenyl ring with respect to the fused-ring system [dihedral angles = 8.32 (8)° (A) and 28.32 (8)° (B)]. In the crystal, the A mol­ecules are connected into a linear supra­molecular chain along the a axis via C—H⋯O inter­actions and linked to this via C—H⋯Cl inter­actions are the B mol­ecules. The chains are connected into layers in the ab plane by π–π inter­actions between pyrazole (A) and pyran (B) rings, and between pyrazole (B) and pyran (A) rings [centroid–centroid distances = 3.5442 (11) and 3.4022 (10) Å, respectively].

Partial Text

For the analgesic and anti-inflammatory activity of pyrano[2,3-c]pyrazole derivatives, see: Kuo et al. (1984 ▶). For the synthesis, see: Gelin et al. (1983 ▶). For the structure of the derivative without a chloro substituent, see: Asiri et al. (2012 ▶).




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