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

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.

[1]  M. Morsy,et al.  Synthesis and investigation of anti-inflammatory activity and gastric ulcerogenicity of novel nitric oxide-donating pyrazoline derivatives. , 2009, European journal of medicinal chemistry.

[2]  Raymond E. Davis,et al.  Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals , 1995 .

[3]  A. M. Glazer,et al.  A nitrogen‐gas‐stream cryostat for general X‐ray diffraction studies , 1986 .

[4]  H. Fun,et al.  3-(4-Bromophenyl)-5-[4-(dimethylamino)phenyl]-4,5-dihydro-1H-pyrazole-1-carbothioamide , 2011, Acta crystallographica. Section E, Structure reports online.

[5]  M. Palkar,et al.  Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents. , 2009, European journal of medicinal chemistry.

[6]  Olga Kennard,et al.  Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds , 1987 .

[7]  Junfen Li,et al.  Synthesis and spectrum characteristic of four new organic fluorescent dyes of pyrazoline compounds , 2007 .

[8]  Anthony L. Spek,et al.  Structure validation in chemical crystallography , 2009, Acta crystallographica. Section D, Biological crystallography.

[9]  R. Kamble,et al.  One-pot synthesis of pyrazoline derivatised carbazoles as antitubercular, anticancer agents, their DNA cleavage and antioxidant activities. , 2011, European journal of medicinal chemistry.

[10]  M. Abid,et al.  Novel Pd(II) complexes of 1-N-substituted 3-phenyl-2-pyrazoline derivatives and evaluation of antiamoebic activity. , 2008, European journal of medicinal chemistry.

[11]  Hoong-Kun Fun,et al.  5-(4-Methoxyphenyl)-3-(pyridin-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide , 2011, Acta crystallographica. Section E, Structure reports online.

[12]  Yong-Sheng Xie,et al.  The Synthesis, X-ray Crystal Structure and Optical Properties of Novel 5-aryl-3-ferrocenyl-1-pyridazinyl-pyrazoline Derivatives , 2010, Journal of Fluorescence.

[13]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[14]  D. Cremer,et al.  General definition of ring puckering coordinates , 1975 .

[15]  G. G. Stokes "J." , 1890, The New Yale Book of Quotations.