Ethyl 2-(3,4-dimethyl-5,5-dioxo-1H,4H-benzo[e]pyrazolo-[4,3-c][1,2]thia-zin-1-yl)acetate.

In the title mol-ecule, C(15)H(17)N(3)O(4)S, the heterocyclic thia-zine ring adopts a twist-boat conformation, which differs from that in related compounds, with adjacent S and C atoms displaced by 0.981 (4) and 0.413 (5) Å, respectively, on the same side of the mean plane formed by the remaining ring atoms. The mean plane of the benzene ring makes a dihedral angle of 23.43 (14)° with the mean plane of the pyrazole ring. In the crystal, mol-ecules are connected by weak C-H⋯O hydrogen bonds to form a three-dimensional network. The H atoms of the methyl group attached to the pyrazole ring were refined over six sites with equal occupancies.

4-Methyl-3-phenyl-2,4-dihydro-pyrazolo-[4,3-c][1,2]benzothia-zine 5,5-dioxide.

In the title mol-ecule, C(16)H(13)N(3)O(2)S, the heterocyclic thia-zine ring adopts a twist chair conformation with the S atom and an adjacent C atom displaced by 0.946 (5) and 0.405 (6) Å, respectively, on the same side of the mean plane formed by the remaining ring atoms. The mean planes of the benzene rings make dihedral angles of 16.61 (10) and 15.32 (10)° with the mean plane of the pyrazole ring. The mol-ecular structure is consolidated by intra-molecular C-H⋯N inter-actions and the crystal packing is stabilized by N-H⋯O and C-H⋯N hydrogen bonds. The crystal studied was an inversion twin with the refined ratio of the twin components being 0.53 (11):0.47 (11).

Propan-2-yl 2-(1,1,3-trioxo-2,3-dihydro-1λ(6),2-benzothia-zol-2-yl)acetate.

In the title mol-ecule, C(12)H(13)NO(5)S, the benzisothia-zole ring system is essentially planar (r.m.s. deviation = 0.0169 Å) as is the -C-C(=O)-O-C- sequence of atoms in the vicinity of the acetate group (r.m.s. deviation = 0.0044 Å). The mean plane of these atoms forms a dihedral angle of 88.41 (7)° with the benzisothia-zole ring system. In the crystal, weak C-H⋯O hydrogen bonds involving methyl-ene and methyne H atoms form R(4) (3)(20) graph-set motifs.

2-[2-(2-Chloro-phen-yl)-2-oxoeth-yl]-2,3-dihydro-1λ(6),2-benzothia-zole-1,1,3-trione.

The asymmetric unit of the title compound, C(15)H(10)ClNO(4)S, contains two independent conformers wherein the 2-chloro-phenyl group in one is rotated by approximately 180° compared to the other mol-ecule. This affects the S-N-C-C(=O) and N-C-C(=O)-C torsion angles giving vlaues of -87.0 (2) and 158.7 (2)° in one mol-ecule and -104.3 (2) and -173.4 (2)° in the other. The benzisothia-zole ring systems in the two mol-ecules are essentially planar (r.m.s. deviations = 0.017 and 0.010 Å) and form dihedral angles of 73.53 (7) and 73.26 (6)° with the benzene rings. In the crystal, there are weak π-π inter-actions between the benzene rings of the benzisothia-zole groups and symmetry-related chloro-benzene rings with centroid-centroid distances of 3.6178 (13) and 3.6267 (15) Å. In addition, pairs of weak inter-molecular C-H⋯O hydrogen bonds form inversion dimers which are connected by further C-H⋯O hydrogen bonds into a three-dimensional network.

2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo-[4,3-c][1,2]benzothia-zin-2-yl)-N-(2-fluoro-benz-yl)acetamide.

In the title mol-ecule, C(20)H(19)FN(4)O(3)S, the heterocyclic thia-zine ring adopts a half-chair conformation with the S atom displaced by 0.668 (4) Šfrom the mean plane formed by the remaining ring atoms. The mean planes of the benzene and pyrazole rings are inclined with respect to each other at a dihedral angle of 17.4 (3)°. The acetamide chain (O/N/C/C/C) linking the pyrazole and 2-fluoro-benzyl rings is essentially planar (r.m.s. deviation = 0.030 Å) and forms dihedral angles with the mean planes of these rings of 78.8 (2) and 78.89 (14)°, respectively. The crystal structure is stabilized by N-H⋯O and C-H⋯O hydrogen-bonding inter-actions, resulting in a six-membered ring with an R(2) (1)(6) motif, while C-H⋯O and C-H⋯F hydrogen-bonding inter-actions result in chains of mol-ecules lying along the c axis in a zigzag fashion.

4-Hy-droxy-2-methyl-1,1-dioxo-N-phenyl-2H-1λ(6),2-benzothia-zine-3-carboxamide.

In the title mol-ecule, C(16)H(14)N(2)O(4)S, the thia-zine ring adopts a twist chair conformation with the N and adjacent C atom displaced by 0.966 (3) and 0.386 (4) Å, respectively, on the same side of the mean plane formed by the remaining ring atoms. The dihedral angle between the mean planes of the benzene rings is 37.65 (10)°. The mol-ecular structure features an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds.

2-[2-(2-Bromo-phen-yl)-2-oxoeth-yl]-1λ(6),2-benzothia-zole-1,1,3-trione.

The asymmetric unit of the title compound, C(15)H(10)BrNO(4)S, contains two different conformers in which the benzisothia-zole rings are essentially planar, with r.m.s. deviations of 0.012 and 0.017 Å. The mean planes of the benzene rings form dihedral angles 70.49 (13) and 72.79 (11)° with the benzisothia-zole rings. The orientation of the Br atoms in the two conformers exhibit the most pronounced difference, with opposing orientations in the two mol-ecules. The crystal structure is stabilized by π-π inter-actions between the benzene rings of the benzisothia-zole moieties of one mol-ecule and bromo-benzene rings of the other mol-ecule, with distances between the ring centroids of 3.599 (3) and 3.620 (3) Å, respectively. The crystal packing is further consolidated by pairs of weak inter-molecular C-H⋯O hydrogen bonds, which form inversion dimers.

N-Benzyl-4-hy-droxy-2-methyl-1,1-dioxo-2H-1λ(6),2-benzothia-zine-3-carboxamide.

In the title mol-ecule, C(17)H(16)N(2)O(4)S, the heterocyclic thia-zine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.546 (4) and 0.281 (4) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O hydrogen bond. The two aromatic rings are inclined to one another by 42.32 (11)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers. The dimers are linked via a series of C-H⋯O inter-actions, leading to the formation of a three-dimensional network.

2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo-[4,3-c][1,2]benzothia-zin-2-yl)acetic acid.

In the title mol-ecule, C(13)H(13)N(3)O(4)S, the heterocyclic thia-zine ring adopts a half-chair conformation in which the S and an adjacent C atom are displaced by 0.919 (3) and 0.300 (4) Å, respectively, on the same side of the mean plane formed by the remaining ring atoms. The mean planes of the benzene and pyrazole rings are inclined at a dihedral angle of 18.32 (12)° with respect to each other. The acetate group is oriented at 80.75 (8)° with respect to the pyrazole ring. The crystal structure is stabilized by O-H⋯N and C-H⋯O hydrogen bonds, resulting in fused eight- and seven-membered rings with R(2) (2)(8) and R(2) (2)(7) graph-set motifs, respectively.

1-(4-Chloro-phen-yl)-2-[4-hy-droxy-3-(3-meth-oxy-benzo-yl)-1,1-dioxo-2H-1λ(6),2-benzothia-zin-2-yl]ethanone.

In the title mol-ecule, C(24)H(18)ClNO(6)S, the heterocyclic thia-zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.406 (5) and 0.444 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The meth-oxy-benzoyl and the chloro-phenyl rings lie roughly parallel to each other, with a dihedral angle between the mean planes of these rings of 8.86 (10)°. The mol-ecular structure is consolidated by intra-molecular O-H⋯O and C-H⋯O inter-actions and the crystal packing is stabilized by inter-molecular O-H⋯O and C-H⋯Cl hydrogen bonds.

3-[Hy-droxy(3-meth-oxy-phen-yl)methyl-idene]-2-(2-oxo-2-phenyl-eth-yl)-3,4-dihydro-2H-1λ(6),2-benzothia-zine-1,1,4-trione.

In the title mol-ecule, C(24)H(19)NO(6)S, the heterocyclic thia-zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.180 (5) and 0.497 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The benzene rings of the benzothia-zine unit and the meth-oxy-phenyl group are almost coplanar, with the dihedral angle between the mean planes of these rings being 5.9 (2)°, while the benzene ring of the 2-oxo-2-phenyl-ethyl group is inclined at 79.68 (11) and 81.01 (10)°, respectively, to these rings. The mol-ecular structure is consolidated by intra-molecular O-H⋯O and C-H⋯N inter-actions, and the crystal packing is stabilized by weak C-H⋯O hydrogen bonds.

2-[2-(3-Chloro-phen-yl)-2-oxoeth-yl]-4-hy-droxy-3-(3-meth-oxy-benzo-yl)-2H-1λ(6),2-benzothia-zine-1,1-dione.

In the title mol-ecule, C(24)H(18)ClNO(6)S, the heterocyclic thia-zine ring adopts a half chair conformation with the S and N atoms displaced by 0.318 (3) and 0.387 (3) Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The benzene rings of the benzothia-zin unit and meth-oxy-benzoyl group are more or less coplanar, the dihedral angle between the mean planes of these rings being 12.37 (10)° while the chloro-phenyl ring is inclined at 81.87 (4) and 73.30 (5)°, respectively, to these rings. The mol-ecular structure is consolidated by intra-molecular O-H⋯O and C-H⋯N inter-actions and the crystal packing is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

(2-Chloro-phen-yl)(4-hy-droxy-1,1-dioxo-2H-1,2-benzothia-zin-3-yl)methanone.

In the title mol-ecule, C(15)H(10)ClNO(4)S, the heterocyclic thia-zine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.527 (7) and 0.216 (7) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The mol-ecular structure is consolidated by an intra-molecular O-H⋯O inter-action and the crystal packing is stabilized by N-H⋯O and C-H⋯O hydrogen bonds.

[2-(2,5-Dichloro-benz-yl)-4-hy-droxy-1,1-dioxo-2H-1,2-benzothia-zin-3-yl](phen-yl)methanone.

In the title mol-ecule, C(22)H(15)Cl(2)NO(4)S, the heterocyclic thia-zine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.343 (5) and 0.402 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The mol-ecular structure is consolidated by an intra-molecular O-H⋯O hydrogen bond, which generates an S(?) ring. In the crystal, the molecules are linked by C-H⋯O interactions into [010] chains.

(2-Bromo-phen-yl)(4-hy-droxy-1,1-dioxo-2H-1,2-benzothia-zin-3-yl)methanone.

In the title mol-ecule, C(15)H(10)BrNO(4)S, the heterocyclic thia-zine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.554 (7) and 0.198 (8) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The mol-ecular structure is consolidated by intra-molecular O-H⋯O inter-actions and the crystal packing features N-H⋯O and C-H⋯O hydrogen bonds.

2-(N-Cyclo-hexyl-carbamo-yl)benzene-sulfonamide.

The asymmetric unit of the title compound, C(13)H(18)N(2)O(3)S, contains two mol-ecules with similar conformations. In both mol-ecules, the cyclo-hexyl rings adopt chair conformations, with the attached N atom in an equatorial orientation and an intra-molecular N-H⋯O hydrogen bond generates an S(7) ring. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules and a C-H⋯O hydrogen bond is also observed. The crystal studied was a racemic twin.

2-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo-[4,3-c][1,2]benzothia-zin-2-yl)-1-(4-meth-oxy-phen-yl)ethanone.

In the title mol-ecule, C(20)H(19)N(3)O(4)S, the heterocyclic thia-zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.492 (6) and 0.199 (6) Å, respectively, on opposite sides from the mean plane formed by the remaining ring atoms. The ethanone group lies at an angle of 9.4 (2)° with respect to the benzene ring, which lies almost perpendicular to the pyrazole ring, with a dihedral between the two planes of 78.07 (9)°. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds.

3-[4-(3,4-Dimethyl-5,5-dioxo-2H,4H-pyrazolo-[4,3-c][1,2]benzothia-zin-2-yl)phen-yl]-2-hy-droxy-1-mesitylprop-2-en-1-one hexane hemisolvate.

In the title compound, C(29)H(27)N(3)O(4)S·0.5C(6)H(14), the heterocyclic thia-zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.500 (5) and 0.229 (5) Å, respectively, on opposite sides from the mean plane formed by the remaining ring atoms. The mean planes of the pyrazole ring and the benzene ring bonded to it form a dihedral angle of 35.76 (11)° and an intra-molecular O-H⋯O hydrogen bond ocurs. The crystal structure features O-H⋯O and C-H⋯O hydrogen bonds. There is a half-mol-ecule of hexane in the asymmetric unit lying about an inversion center. It is disordered over two sets of sites with occupancy factors 0.590 (9) and 0.410 (9).

3,4-Dimethyl-2-(2-oxo-2-phenyl-eth-yl)-2H,4H-pyrazolo-[4,3-c][1,2]benzothia-zine-5,5-dione.

In the title mol-ecule, C(19)H(17)N(3)O(3)S, the heterocyclic thia-zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.530 (5) and 0.229 (6) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The ethanone group lies at an angle of 3.8 (3)° with respect to the benzene ring, which lies almost perendicular to the pyrazole ring, with a dihedral between the two planes of 89.22 (11)°. Weak inter-molecular C-H⋯O hydrogen-bonding inter-actions are present.

3-[(3-Benzoyl-4-hy-droxy-1,1-dioxo-2H-1λ,2-benzothia-zin-2-yl)meth-yl]benzo-nitrile.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(23)H(17)N(2)O(4)S, with significant differences in their conformations, e.g. the benzene rings of the benzothia-zine and benzonitrile units are inclined at 28.19 (10) and 17.89 (7)° in the two mol-ecules, with the centroids of the rings separated by 3.975 (2) and 3.637 (2) Å, respectively. Moreover, the N-C-C-C torsion angles involving the benzoyl group are 14.3 (5) and 8.2 (5)° in the two mol-ecules, showing different degrees of rotation of this group. In both mol-ecules, the heterocyclic thia-zine rings adopt half-chair conformations, with the S and N atoms displaced by 0.427 (6) and 0.365 (6) Å, respectively, in one mol-ecule and by 0.356 (6) and 0.432 (6) Å, respectively, in the other, on opposite sides of the mean planes formed by the remaining ring atoms. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds and further consolidated by intra-molecular O-H⋯O hydrogen bonds.