4-[5-(Furan-2-yl)-3-trifluoromethyl-1H-pyrazol-1-yl]benzenesulfonamide

In the title compound, C14H10F3N3O3S, there are significant twists in the molecule, as seen in the values of the dihedral angles between the pyrazole ring and each of the furan [31.1 (2)°] and benzene rings [55.58 (10)°]. The amino N atom occupies a position almost normal to the benzene ring [N—S—Car—Car (ar = aromatic) torsion angle = 83.70 (19)°]. One amino H atom forms a hydrogen bond to the tricoordinate pyrazole N atom and the other interacts with a sulfonamide O atom, forming a supramolecular chain along [010]. The chains are consolidated into a supramolecular layers via C—H⋯O interactions involving the second sulfonamide O atom; layers stack along [10-1]. The furan ring was found to be disordered over two diagonally opposite orientations of equal occupancy.

In the title compound, C 14 H 10 F 3 N 3 O 3 S, there are significant twists in the molecule, as seen in the values of the dihedral angles between the pyrazole ring and each of the furan [31.1 (2) ] and benzene rings [55.58 (10) ]. The amino N atom occupies a position almost normal to the benzene ring [N-S-C ar -C ar (ar = aromatic) torsion angle = 83. 70 (19) ]. One amino H atom forms a hydrogen bond to the tricoordinate pyrazole N atom and the other interacts with a sulfonamide O atom, forming a supramolecular chain along [010]. The chains are consolidated into a supramolecular layers via C-HÁ Á ÁO interactions involving the second sulfonamide O atom; layers stack along [101]. The furan ring was found to be disordered over two diagonally opposite orientations of equal occupancy.

Tiekink Comment
The title CF 3 -derivatized sulfonamide (I), was investigated. in connection with on-going studies of sulfonamides, both biological (Croitoru et al., 2004;Dogruer et al., 2010) and crystallographic (Asiri et al., 2011;Asiri et al., 2012). In particular, fluoride in the form of a trifluoromethyl group, which has long been recognized in medicinal chemistry for its ability to alter the physico-chemical and biological characteristics of molecules (Fokin & Kolomiyets, 1988;Bonacorso et al., 2006), is featured in the new molecule to promote enhanced biological properties.
In (I), Fig. 1, the dihedral angle of 31.1 (2)° between the furanyl and pyrazole rings indicates a significant twist between these rings. Similarly, the dihedral angle of 55.58 (10)° between the pyrazole ring and the benzene ring to which it is connected indicates a significant twist. The amino-N3 atom occupies a position almost normal to the benzene ring, forming a N3-S1-C12-C13 torsion angle of 83.70 (19)°. This allows the participation of both N-H atoms in hydrogen bonding interactions.
One amino-H atom forms a hydrogen bond to the pyrazole-N2 atom of a centrosymmetrically related molecule to form an 18-membered {···HNSC 4 NN} 2 synthon, Table 1. These are connected into a supramolecular chain via a N-H···O(sulfonamide) hydrogen bonding, Fig. 2

Refinement
Carbon-bound H-atoms were placed in calculated positions [C-H = 0.95 Å; U iso (H) = 1.2U eq (C)] and were included in the refinement in the riding model approximation. The N-H atoms were located in a difference Fourier map, and were refined with a distance restraint of N-H = 0.88±0.01 Å; their U iso values were refined.
The furyl ring is disordered over two positions; the disorder could not be refined, and was assumed as a 1:1 type of disorder. The ring was refined as a rigid pentagon of 1.35 Å sides. The U ij values of C6′ was equated to those of O6 (as well as the O1′/C6, C5′/C5, C6′/O1, C7′/C8 and C8′/C7 pairs). The benzene ring was refined as a rigid hexagon of 1.39 Å sides.
Owing to poor agreement, the (8 0 10) reflection was omitted from the final cycles of refinement.

Figure 1
The molecular structure of (I) showing displacement ellipsoids at the 70% probability level. Only one orientation of the disordered furanyl ring is shown.     (1) 3.032 (4) 170 (4)