Research Article: 3-(4-Chloro­phen­yl)-5-(thio­phen-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide

Date Published: February 01, 2012

Publisher: International Union of Crystallography

Author(s): Hoong-Kun Fun, Thitipone Suwunwong, Suchada Chantrapromma.


In the title pyrazoline derivative, C14H12ClN3S2, the thiophene ring is disordered over two orientations with a refined site-occupancy ratio of 0.832 (4):0.168 (4). The pyrazoline ring adopts an envelope conformation with the C atom linking the thiophene ring at the flap. The dihedral angles between the benzene ring and the major and minor components of the thiophene ring are 88.6 (3) and 85.6 (15)°, respectively while the dihedral angle between the disorder components of the ring is 3.1 (16)°. The mean plane of the pyrazoline ring makes dihedral angles of 11.86 (13), 80.1 (3) and 83.0 (15)°, respectively, with the benzene ring, and the major and minor components of the thiophene ring. An intra­molecular N(amide)—H⋯N(pyrazoline) hydrogen bond generates an S(5) ring motif. In the crystal, mol­ecules are linked by weak C—H⋯S and N(amide)—H⋯S inter­actions into a tape along [10]. C—H⋯π inter­actions are also observed.

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For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For related structures, see: Fun et al. (2011 ▶); Nonthason et al. (2011 ▶). For background to and applications of pyrazoline derivatives, see: Bai et al. (2007 ▶); Gong et al. (2011 ▶); Husain et al. (2008 ▶); Khode et al. (2009 ▶); Shoman et al. (2009 ▶); Taj et al. (2011 ▶). For the stability of the temperature controller, see: Cosier & Glazer (1986 ▶).