Crystal structure, Hirshfeld surface analysis and inter-action energy, DFT and anti-bacterial activity studies of (Z)-4-hexyl-2-(4-methyl-benzyl-idene)-2H-benzo[b][1,4]thia-zin-3(4H)-one.

The title compound, C22H25NOS, consists of methyl-benzyl-idene and benzo-thia-zine units linked to a hexyl moiety, where the thia-zine ring adopts a screw-boat conformation. In the crystal, inversion dimers are formed by weak C-HMthn⋯OBnzthz hydrogen bonds and are linked into chains extending along the a-axis direction by weak C-HBnz⋯OBnzthz (Bnz = benzene, Bnzthz = benzo-thia-zine and Mthn = methine) hydrogen bonds. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (59.2%) and H⋯C/C⋯H (27.9%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HBnz⋯OBnzthz and C-HMthn⋯OBnzthz hydrogen-bond energies are 75.3 and 56.5 kJ mol-1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap. Moreover, the anti-bacterial activity of the title compound was evaluated against gram-positive and gram-negative bacteria.

Crystal structure, Hirshfeld surface analysis, inter-action energy and DFT studies of (2Z)-2-(2,4-di-chloro-benzyl-idene)-4-nonyl-3,4-di-hydro-2H-1,4-benzo-thia-zin-3-one.

The title compound, C24H27Cl2NOS, contains 1,4-benzo-thia-zine and 2,4-di-chloro-phenyl-methyl-idene units in which the di-hydro-thia-zine ring adopts a screw-boat conformation. In the crystal, inter-molecular C-HBnz⋯OThz (Bnz = benzene and Thz = thia-zine) hydrogen bonds form chains of mol-ecules extending along the a-axis direction, which are connected to their inversion-related counterparts by C-HBnz⋯ClDchlphy (Dchlphy = 2,4-di-chloro-phen-yl) hydrogen bonds and C-HDchlphy⋯π (ring) inter-actions. These double chains are further linked by C-HDchlphy⋯OThz hydrogen bonds, forming stepped layers approximately parallel to (012). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (44.7%), C⋯H/H⋯C (23.7%), Cl⋯H/H⋯Cl (18.9%), O⋯H/H⋯O (5.0%) and S⋯H/H⋯S (4.8%) inter-actions. Hydrogen-bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, C-HDchlphy⋯OThz, C-HBnz⋯OThz and C-HBnz⋯ClDchlphy hydrogen-bond energies are 134.3, 71.2 and 34.4 kJ mol-1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap. The two carbon atoms at the end of the nonyl chain are disordered in a 0.562 (4)/0.438 (4) ratio.

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of (2Z)-4-benzyl-2-(2,4-di-chloro-benzyl-idene)-2H-1,4-benzo-thia-zin-3(4H)-one.

The title compound, C22H15Cl2NOS, contains 1,4-benzo-thia-zine and 2,4-di--chloro-benzyl-idene units, where the di-hydro-thia-zine ring adopts a screw-boat conformation. In the crystal, inter-molecular C-HBnz⋯OThz (Bnz = benzene and Thz = thia-zine) hydrogen bonds form corrugated chains extending along the b-axis direction which are connected into layers parallel to the bc plane by inter-molecular C-HMethy⋯SThz (Methy = methyl-ene) hydrogen bonds, en-closing R 4 4(22) ring motifs. Offset π-stacking inter-actions between 2,4-di--chloro-phenyl rings [centroid-centroid = 3.7701 (8) Å] and π-inter-actions which are associated by C-HBnz⋯π(ring) and C-HDchlphy⋯π(ring) (Dchlphy = 2,4-di-chloro-phen-yl) inter-actions may be effective in the stabilization of the crystal structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (29.1%), H⋯C/C⋯H (27.5%), H⋯Cl/Cl⋯H (20.6%) and O⋯H/H⋯O (7.0%) inter-actions. Hydrogen-bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HBnz⋯OThz and C-HMethy⋯SThz hydrogen-bond energies are 55.0 and 27.1 kJ mol-1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 3-{(2Z)-2-[(2,4-di-chloro-phen-yl)methyl-idene]-3-oxo-3,4-di-hydro-2H-1,4-benzo-thia-zin-4-yl}propane-nitrile.

The title compound, C18H12Cl2N2OS, consists of a di-hydro-benzo-thia-zine unit linked by a -CH group to a 2,4-di-chloro-phenyl substituent, and to a propane-nitrile unit is folded along the S⋯N axis and adopts a flattened-boat conformation. The propane-nitrile moiety is nearly perpendicular to the mean plane of the di-hydro-benzo-thia-zine unit. In the crystal, C-HBnz⋯NPrpnit and C-HPrpnit⋯OThz (Bnz = benzene, Prpnit = propane-nitrile and Thz = thia-zine) hydrogen bonds link the mol-ecules into inversion dimers, enclosing R 2 2(16) and R 2 2(12) ring motifs, which are linked into stepped ribbons extending along [110]. The ribbons are linked in pairs by complementary C=O⋯Cl inter-actions. π-π contacts between the benzene and phenyl rings, [centroid-centroid distance = 3.974 (1) Å] may further stabilize the structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (23.4%), H⋯Cl/Cl⋯H (19.5%), H⋯C/C⋯H (13.5%), H⋯N/N⋯H (13.3%), C⋯C (10.4%) and H⋯O/O⋯H (5.1%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry calculations indicate that the two independent C-HBnz⋯NPrpnit and C-HPrpnit⋯OThz hydrogen bonds in the crystal impart about the same energy (ca 43 kJ mol-1). Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

Crystal structure, Hirshfeld surface analysis and DFT study of (2Z)-2-(2,4-di-chloro-benzyl-idene)-4-[2-(2-oxo-1,3-oxazolidin-3-yl)eth-yl]-3,4-di-hydro-2H-1,4-benzo-thia-zin-3-one.

The title compound, C20H16Cl2N2O3S, is built up from a di-hydro-benzo-thia-zine moiety linked by -CH- and -C2H4- units to 2,4-di-chloro-phenyl and 2-oxo-1,3-oxazolidine substituents, where the oxazole ring and the heterocyclic portion of the di-hydro-benzo-thia-zine unit adopt envelope and flattened-boat conformations, respectively. The 2-carbon link to the oxazole ring is nearly perpendicular to the mean plane of the di-hydro-benzo-thia-zine unit. In the crystal, the mol-ecules form stacks extending along the normal to (104) with the aromatic rings from neighbouring stacks inter-calating to form an overall layer structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (28.4%), H⋯Cl/Cl⋯H (19.3%), H⋯O/O⋯H (17.0%), H⋯C/C⋯H (14.5%) and C⋯C (8.2%) inter-actions. Weak hydrogen-bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/ 6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

Crystal structure, Hirshfeld surface analysis and DFT study of (2Z)-2-(4-fluoro-benzyl-idene)-4-(prop-2-yn-1-yl)-3,4-di-hydro-2H-1,4-benzo-thia-zin-3-one.

The title compound, C18H12FNOS, is built up from a 4-fluoro-benzyl-idene moiety and a di-hydro-benzo-thia-zine unit with a propynyl substituent, with the heterocyclic portion of the di-hydro-benzo-thia-zine unit adopting a shallow boat conformation with the propynyl substituent nearly perpendicular to it. The two benzene rings are oriented at a dihedral angle of 43.02 (6)°. In the crystal, C-HFlurphen⋯FFlurphen (Flurphen = fluoro-phen-yl) hydrogen bonds link the mol-ecules into inversion dimers, enclosing R 2 2(8) ring motifs, with the dimers forming oblique stacks along the a-axis direction. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (33.9%), H⋯C/C⋯H (26.7%), H⋯F/F⋯H (10.9%) and C⋯C (10.6%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

Crystal structure and Hirshfeld surface analysis of 1-{[2-oxo-3-(prop-1-en-2-yl)-2,3-di-hydro-1H-1,3-benzo-diazol-1-yl]meth-yl}-3-(prop-1-en-2-yl)-2,3-di-hydro-1H-1,3-benzo-diazol-2-one.

In the title compound, C21H20N4O2, the intra-molecular C-H⋯O hydrogen-bonded benzo-diazo-lone moieties are planar to within 0.017 (1) and 0.026 (1) Å, and are oriented at a dihedral angle of 57.35 (3)°. In the crystal, two sets of inter-molecular C-H⋯O hydrogen bonds generate layers parallel to the bc plane. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (51.8%), H⋯C/C⋯H (30.7%) and H⋯O/O⋯H (11.2%) inter-actions.