N′-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene)benzenesulfonohydrazide

The molecule of the title compound, C14H10FN3O3S, consists of an indole unit and a phenylsulfonyl unit that are disposed in an approximately trans orientation relative to the N—N single bond. Two molecules are arranged about a center of inversion, forming a hydrazide–carbonyl N—H⋯O hydrogen-bonded dimer; the dimers are linked by an indole–sulfonyl N—H⋯O hydrogen bond into a ribbon.

The molecule of the title compound, C 14 H 10 FN 3 O 3 S, consists of an indole unit and a phenylsulfonyl unit that are disposed in an approximately trans orientation relative to the N-N single bond. Two molecules are arranged about a center of inversion, forming a hydrazide-carbonyl N-HÁ Á ÁO hydrogen-bonded dimer; the dimers are linked by an indole-sulfonyl N-HÁ Á ÁO hydrogen bond into a ribbon.

Comment
We have reported the crystal structures of 3-indole benzenesulfonohydrazides (Ali et al., 2007a(Ali et al., , 2007b(Ali et al., , 2007c. The studies continue with the benzenesulfonohydrazide that is obtained by condensing benzenesulfonohydrazine with a substituted 1H-indol-2,3-dione, 5-fluroisatin. This compound exists as a hydrogen-bonded dimer (Naumov et al., 2000). The title compound (Scheme I) has the indolyl fused-ring portion and the phenylsulfonyl portion disposed in an approximately transalignment relative to the N-N single-bond ( Fig. 1). Two molecules are arranged about a center-of-inversion to form an N-H hydrazide ···O carbonyl hydrogen-bonded dimer; the dimers are linked by another N-H indole ···O sulfonyl hydrogen bond into a ribbon structure (Fig. 2).

Refinement
The carbon-bound H atoms were placed at calculated positions (C-H 0.95 Å), and were included in the refinement in the riding model approximation with U(H) set to 1.2U eq (C). The amino H atoms were located in a difference Fouier map, and were refined with a distance restraint of N-H 0.88±0.01 Å.  supplementary materials

Special details
Experimental. A medium-focus collimator of 0.8 mm diameter was used on the diffractometer to measure the somewhat large crystal.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.