Received 2 December 2012
aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,bLake Braddock Secondary School, 9200 Burke Lake Road, Burke, VA 22015, USA,cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: email@example.com
In the title compound, C19H17Cl2N3O2, the amide group is planar and, through N-HO hydrogen bonding to an adjoining molecule, forms dimers of the R22(10) type. As a result of steric repulsion, the amide group is rotated with respect to both the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 71.63 (11) and 57.93 (10)°, respectively. The dihedral angle between the dichlorophenyl and 2,3-dihydro-1H-pyrazol-4-yl rings is 76.60 (10)° while that between the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings is 49.29 (7)°. The crystal structure also features weak C-HO interactions.
N-Substituted 2-arylacetamides are of interest because of their structural similarity to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006); Mijin et al. (2008). For amides as ligands, see: Wu et al. (2008, 2010). For the structures of acetamide derivatives, see: Fun et al. (2011a,b, 2012a,b). For a description of the Cambridge Structural Database, see: Allen (2002). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5277 ).
BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and the DST-PURSE financial assistance. RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.
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