(Z)-2-Benzylidene-3-n-butoxy-2H-1,4-benzothiazine

Abstract

In the title compound, C19H19NOS, the thiazin-3-one ring of the 1,4-thiazin-3-one moiety adopts a screw-boat conformation. The dihedral angle between the benzene rings is 31.0 (5)°. An intramolecular C—H...S hydrogen bond forms anS(6) ring motif. In the crystal, C—H...π(ring) contacts form inversion dimers and weak π–π stacking interactions, with a centroid-to-centroid distance of 3.8766 (2) Å, also occur.

Crystal structure, Hirshfeld surface analysis and DFT study of (2Z)-2-(2,4-dichlorobenzylidene)-4-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-3,4-dihydro-2H-1,4-benzothiazin-3-one

“…11) gave 14 hits with R 1 = Ph and R 2 = CH 2 COOH (Sebbar et al, 2016c), n-octadecyl (Sebbar et al, 2017a), CH 2 C CH (Sebbar et al, 2014a), IIa (Sebbar et al, 2016a), CH 2 COOEt (Zerzouf et al, 2001), IIb (Ellouz et al, 2015a), n-Bu (Sebbar et al, 2014b), IIc (Sebbar et al, 2016d), Me (Ellouz et al, 2015b) and IId (Sebbar et al, 2015). In addition, there are structures with R 1 = 4-ClC 6 H 4 and R 2 = CH 2 Ph2 (Ellouz et al, 2016c), n-Bu (Ellouz et al, 2017a), IIa (Ellouz et al, 2017c) and R 1 = 2-ClC 6 H 4 , R 2 = CH 2 C CH (Sebbar et al, 2017b). In the majority of these, the heterocyclic ring is quite non-planar with the dihedral angle between the plane defined by the benzene ring plus the nitrogen and sulfur atoms and that defined by nitrogen and sulfur and the other two carbon atoms separating them ranging from ca 29 in CH 2 C CH (Sebbar et al, 2014a), to 36 in IId (Sebbar et al, 2015), which includes the value of ca 30 for 2H-1,4-benzothiazin-3(4H)-one (WAKLUQ 01; Merola, 2013).…”

Crystal structure, Hirshfeld surface analysis, interaction energy and DFT studies of (2Z)-2-(2,4-dichlorobenzylidene)-4-nonyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

“…1.7589 18 The largest set contains IIa (COGRUN; Sebbar et al, 2014a), IIb (APAJUY; Sebbar et al, 2016c), IIc (EVIYIT; Sebbar et al, 2016b) and IId (WUFGIP; Sebbar et al, 2015b). Additional examples are III: R 1 = 4-FC 6 H 4 and R 2 = CH 2 C CH (WOCFUS; Hni et al, 2019a), R 1 = 4-ClC 6 H 4 and R 2 = CH 2 Ph (OMEGEU; Ellouz et al, 2016c) and R 1 = 2-ClC 6 H 4 , R 2 = CH 2 C CH (SAVTUH; Sebbar et al, 2017). In all these compounds, the configuration about the benzylidene group: C CHC 6 H 5 bond is Z, and in the majority of these, the heterocyclic ring is quite non-planar with the dihedral angle between the plane defined by the benzene ring plus the nitrogen and sulfur atoms and that defined by nitrogen and sulfur and the other two carbon atoms separating them having approximate values of 36 (WUFGIP), 29 (APAJUY), 28 (SAVTUH), 26 (WOCFUS) and 25 (COGRUN).…”

Crystal structure, Hirshfeld surface analysis and interaction energy, DFT and antibacterial activity studies of (Z)-4-hexyl-2-(4-methylbenzylidene)-2H-benzo[b][1,4]thiazin-3(4H)-one

“…A search in the Cambridge Structural Database (Groom et al, 2016), for compounds containing the fragment II (R 1 = Ph, R 2 = C), gave 15 hits, including with R 1 = 4-ClC 6 H 4 and R 2 = CH 2 CH 2 CH 2 CH 3 (IIa) (Ellouz et al, 2017b), R 1 = 2,4-Cl 2 C 6 H 3 and R 2 = CH 2 Ph2 (IIb) (Sebbar et al, 2019b), and R 1 = 2-ClC 6 H 4 , R 2 = CH 2 C CH (IIc) (Sebbar et al, 2017b), R 1 = 4-FC 6 H 4 and R 2 = CH 2 C CH (IIc) (Hni et al,2019a), CH 2 COOH (Sebbar et al, 2016a), R 1 = 2,4-Cl 2 C 6 H 3 and R 2 = (CH 2 ) 8 CH 3 (Hni et al, 2020), R 1 = 4-ClC 6 H 4 and R 2 = CH 2 Ph2 (IIb) (Ellouz et al, 2016), R 1 = 4-ClC 6 H 4 and R 2 = (IId) (Ellouz et al, 2017a) or CH 2 C CH (IIc) (Sebbar et al, 2014), R 1 = 2,4-Cl 2 C 6 H 3 and R 2 = IId (Hni et al, 2019b), R 1 = 2,4-Cl 2 C 6 H 3 and R 2 =CH 2 CH 2 CN (IIe) (Sebbar et al, 2019a), IIf (Sebbar et al, 2016b) and IIg (Ellouz et al, 2015).…”