Crystal structure of (E)-2-benzylidene-4-[(3-phenyl-4,5-dihydroisoxazol-5-yl)methyl]-2H-benzo[b][1,4]thiazin-3(4H)-one

Abstract

In the title compound, C25H20N2O2S, the di­hydro­isoxazole ring exhibits an envelope conformation with the methine atom being the flap, while the 1,4-thia­zine ring displays a screw-boat conformation. The six-membered ring fused to the 1,4-thia­zine ring makes dihedral angles of 63.04 (2) and 54.7 (2)° with the mean planes through the five-membered heterocycle and the attached phenyl ring, respectively. The phenyl group connected to the 1,4-thia­zine ring is disordered over two sites [major component = 0.57 (2)]. The most prominent inter­actions in the crystal structure are C—H⋯O hydrogen bonds that link mol­ecules, forming inversion dimers, and C—H⋯N hydrogen bonds that link the dimers into columns parallel to the b axis.

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 3-{(2Z)-2-[(2,4-dichlorophenyl)methylidene]-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl}propanenitrile

“…A search in the Cambridge Structural Database (Groom et al, 2016;updated to March 2019), for compounds containing the fragment II (R 1 = Ph, R 2 = C), gave 14 hits. With R 1 = Ph and R 2 = CH 2 C CH IIa (Sebbar et al, 2014a), CH 2 COOH IIb (Sebbar et al, 2016c), IIc (Sebbar et al, 2016b) and IIf (Sebbar et al, 2015b), there are other examples with R 1 = 4-FC 6 H 4 and R 2 = CH 2 C CH IIa (Hni et al, 2019a), R 1 = 4-ClC 6 H 4 and R 2 = CH 2 Ph2 IId (Ellouz et al, 2016c) and R 1 = 2-ClC 6 H 4 , R 2 = CH 2 C CH IIa (Sebbar et al, 2017). In all these compounds, the configuration about the benzylidene 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 ranging from ca 29 (IIa) to 36 (IIf).…”

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

“…A search of the Cambridge Crystallographic Database (Groom et al, 2016;updated to Nov. 2018) using the fragment II (R 1 = Ph, R 2 = C; Fig. 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 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). The other three (IIa, IIc and R 1 = 4-ClC 6 H 4 and R 2 = CH 2 Ph2; have the benzothiazine unit nearly planar with a corresponding dihedral angle of ca 3-4 .…”

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).…”