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N-(3,4-Dimethyl-phen-yl)-4-hydr-oxy-2-methyl-2H-1,2-benzothia-zine-3-carboxamide 1,1-dioxide.

ABSTRACT: 1,2-Benzothia-zines similar to the title compound, C(18)H(18)N(2)O(4)S, are well known in the literature for their biological activities and are used as medicines in the treatment of inflammation and rheumatoid arthritis. The thia-zine ring adopts a distorted half-chair conformation. The enolic H atom is involved in an intra-molecular O-H⋯O hydrogen bond, forming a six-membered ring. In the crystal, mol-ecules arrange themselves into centrosymmetric dimers by means of pairs of weak inter-molecular N-H⋯O hydrogen bonds.

SUBMITTER: Siddiqui WA

PROVIDER: S-EPMC2968962 | biostudies-literature | 2009 Mar

REPOSITORIES: biostudies-literature

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N-(3,4-Dimethyl-phen-yl)-4-hydr-oxy-2-methyl-2H-1,2-benzothia-zine-3-carboxamide 1,1-dioxide.

Siddiqui Waseeq Ahmad WA Ali Muhammad M Zia-Ur-Rehman Muhammad M Sharif Saima S Tizzard Graham John GJ

Acta crystallographica. Section E, Structure reports online 20090328 Pt 4

1,2-Benzothia-zines similar to the title compound, C(18)H(18)N(2)O(4)S, are well known in the literature for their biological activities and are used as medicines in the treatment of inflammation and rheumatoid arthritis. The thia-zine ring adopts a distorted half-chair conformation. The enolic H atom is involved in an intra-molecular O-H⋯O hydrogen bond, forming a six-membered ring. In the crystal, mol-ecules arrange themselves into centrosymmetric dimers by means of pairs of weak inter-molecul ...[more]

PMID: 21582605

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N-(2,3-Dimethyl-phen-yl)-4-hydr-oxy-2-methyl-2H-1,2-benzothia-zine-3-carboxamide 1,1-dioxide.

Project description:In the crystal structure of the title compound, C(18)H(18)N(2)O(4)S, the thia-zine ring adopts a distorted half-chair conformation. 1,2-Benzothia-zines of this kind have a wide range of biological activities and are mainly used as medicines in the treatment of inflammation and rheumatoid arthritis. The enolic H atom is involved in an intra-molecular O-H⋯O hydrogen bond, forming a six-membered ring. The mol-ecules arrange themselves into centrosymmetric dimers by means of inter-molecular N-H⋯O hydrogen bonds. A weak inter-molcular C-H⋯O inter-action is also present.

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Project description:In the title compound, C(15)H(11)ClN(2)O(4)S, there are two independent mol-ecules in the asymmetric unit, in which the heterocyclic thia-zine rings in both mol-ecules adopt half-chair conformations. The conformations about the C-C and C-N bonds in the central C-C-N-C chain in both mol-ecules are all EZ. There are strong intra-molecular O-H⋯O and N-H⋯N hydrogen bonds resulting in graph-set patterns S(6) and S(5) for the oxo and amino rings, in addition to intra-molecular N-H⋯Cl inter-actions. In the crystal structure, mol-ecules are linked by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds into chains along [100].

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Project description:There are two mol-ecules in the asymmetric unit of the title compound, C(15)H(11)NO(4)S. The heterocyclic thia-zine rings in both mol-ecules adopt half-chair conformations with the S and N atoms displaced by 0.455 (4) and 0.254 (4) Å, respectively, in one mol-ecule, and 0.480 (4) and 0.224 (5) Å in the other, on opposite sides of the mean planes formed by the remaining ring atoms. The crystal structure is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds. In addition, intra-molecular O-H⋯O inter-actions are also present.

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Project description:The asymmetric unit of the title compound, C(10)H(9)NO(5)S, contains two independent mol-ecules. The heterocyclic thia-zine rings in both mol-ecules adopt half-chair conformations, with the S atoms in each mol-ecule displaced by 0.455 (3) and 0.539 (3) Å and the N atoms displaced in the opposite direction by 0.214 (3) and 0.203 (3) Å, from the planes defined by the remaining ring atoms. The crystal structure is stabilized by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds involving both inter- and intra-molecular inter-actions.

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Project description:In the mol-ecule of the title compound, C(10)H(9)NO(6)S·H(2)O, the benzothia-zine ring adopts an envelope conformation. An intra-molecular N-H⋯O hydrogen bond results in the formation of a nonplanar five-membered ring which has a twisted conformation. In the crystal structure, inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules to form a three-dimensional network. There is a π-π contact between the benzene rings [centroid-centroid distance = 3.972 (2) Å].

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