N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-fluorobenzenesulfonamide

Abstract

In the title compound, C14H12FNO4S, the dihedral angle between the aromatic rings is 50.26 (9)° and the C—S—N—C bond adopts a gauche conformation [torsion angle = −68.12 (15)°]. The dihydro­dioxine ring is disordered over two orientations, which both approximate to half-chairs, in a 0.880 (7):0.120 (7) ratio. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into C(4) chains propagating in [100]. Weak C—H⋯O and C—H⋯F inter­actions consolidate the packing.

2,5-Dichloro-N-(2,3-dimethylphenyl)benzenesulfonamide

“…The dihedral angle between the C1-C6 and C9-C14 benzene rings in (I) is 62.21 (7)°. The C1-N1-S1-C9 linkage adopts a near-ideal gauche conformation [torsion angle = 60.22 (17)°] and the bond-angle sum about N1 (H atom freely refined) is 349°, possibly suggesting a hybridization state intermediate between sp 2 and sp 3 , which was also observed in a related compound (Mughal et al, 2012a). The largest bond angle at the distorted tetrahedral S atom is O1-S1-O2…”

“…to generate C(4) chains propagating in[010]: adjacent molecules are in the chain are generated by glide-symmetry. A similar chain occurs in N-(2,3-dihydro-1,4benzodioxin-6-yl)-4-fluorobenzenesulfonamide(Mughal et al, 2012a), although in this case, adjacent molecules are generated by translational symmetry. Conversely, in 2,5-dichloro-N-(3-methylphenyl)benzenesulfonamide(Mughal et al, 2012b), pairs of N-H•••O interactions lead to inversion dimers in the crystal.…”

2,5-Dichloro-N-(3-methylphenyl)benzenesulfonamide

“…Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97. of sulfonamides (Khan et al, 2011;Mughal et al, 2012).…”

“…The C1-S1-N1-C7 linkage between the rings adopts a gauche conformation [torsion angle = -51.4 (2)°] and the minimum and maximum bond angles at the S atom are 105.52 (12) and 118.51 (12)°, respectively. The largest of these corresponds to the O=S=O bond angle, which is usually the largest in sulfonamindes (Mughal et al, 2012). An intramolecular C-H•••O interaction leads to an S(6) ring.…”

N-(2,3-Dimethylphenyl)-4-fluoro-N-[(4-fluorophenyl)sulfonyl]benzenesulfonamide

“…For related crystal structures, see: Hanson & Hitchcock (2004); Low et al (2006); Mughal et al (2012).…”