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2-[N-(4-Meth-oxy-phen-yl)acetamido]-1,3-thia-zol-4-yl acetate.

ABSTRACT: The structural analysis of the title compound, C14H14N2O4S, particularly the presence of an acetyl group at the exocyclic N atom and the C(H)-C(O2CMe)-N acet-oxy group in the thia-zole ring, may indicate that one of the starting materials, i.e. 2-(4-meth-oxy-anilino)-1,3-thia-zol-4(5H)-one, exists in the reaction mixture, at least partially, as a tautomer with an exocyclic amine N atom and an enol group. The acet-oxy and acetyl groups deviate from the thia-zole plane by 69.17?(6) and 7.25?(19)°, respectively. The thia-zole and benzene rings form a dihedral angle of 73.50?(4)°. In the crystal, centrosymmetrically related mol-ecules are connected into dimeric aggregates via C-H?O inter-actions.

SUBMITTER: Horishny V

PROVIDER: S-EPMC3588441 | biostudies-other | 2013 Mar

REPOSITORIES: biostudies-other

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2-[N-(4-Meth-oxy-phen-yl)acetamido]-1,3-thia-zol-4-yl acetate.

Horishny Volodymyr V Lesyk Roman R Gzella Andrzej K AK

Acta crystallographica. Section E, Structure reports online 20130216 Pt 3

The structural analysis of the title compound, C14H14N2O4S, particularly the presence of an acetyl group at the exocyclic N atom and the C(H)-C(O2CMe)-N acet-oxy group in the thia-zole ring, may indicate that one of the starting materials, i.e. 2-(4-meth-oxy-anilino)-1,3-thia-zol-4(5H)-one, exists in the reaction mixture, at least partially, as a tautomer with an exocyclic amine N atom and an enol group. The acet-oxy and acetyl groups deviate from the thia-zole plane by 69.17 (6) and 7.25 (19)°, ...[more]

PMID: 23476576

Similar Datasets

2-[N-(2,4-Dimeth-oxy-phen-yl)acetamido]-1,3-thia-zol-4-yl acetate.

Project description:The title compound, C15H16N2O5S, is a product of the reaction of 2-(2,4-dimeth-oxy-phenyl-amino)-1,3-thia-zol-4(5H)-one with acetic anhydride. The presence of the acetyl and acet-oxy groups in the mol-ecule indicates that the starting thia-zole exists as a tautomer in the reaction mixture with exocyclic amino and enol moieties. The acetyl group is tilted slightly from the heterocyclic ring plane [dihedral angle = 4.46?(11)°], while the acet-oxy group is almost perpendicular to this ring [dihedral angle = 88.14?(12)°]. An intra-molecular acet-yl-meth-oxy C-H?O inter-action is noted. In the crystal, mol-ecules are connected into a three-dimensional architecture by C-H?O inter-actions.

| S-EPMC3588517 | biostudies-other

{2-[(1,3-Benzo-thia-zol-2-yl)meth-oxy]-5-bromo-phen-yl}(phen-yl)methanone.

Project description:In the title compound, C21H14BrNO2S, the dihedral angle between the planes of the benzo-thia-zole and phenyl-methanone groups is 63.4?(2)°. In the crystal, pairs of C-H?N hydrogen bonds link the mol-ecules to form inversion dimers, which are further linked by C-H?O inter-actions into chains along the c axis. C-H?? and ?-? inter-actions [centroid-centroid distance = 3.863?(1)?Å] further stabilize the mol-ecular assembly.

| S-EPMC3685117 | biostudies-literature

{2-[(1,3-Benzo-thia-zol-2-yl)meth-oxy]-5-fluoro-phen-yl}(4-chloro-phen-yl)methanone.

Project description:The asymmetric unit of the title compound, C21H13ClFNO2S, contains two independent mol-ecules with similar conformations. In the mol-ecules, the thia-zole ring is essentially planar [maximum atomic deviations = 0.014?(4) and 0.023?(5)?Å] and is oriented with respect to the fluoro-phenyl ring and chloro-phenyl rings at 9.96?(18) and 70.39?(18)° in one mol-ecule and at 7.50?(18) and 68.43?(18)° in the other; the dihedral angles between the fluoro-phenyl and chloro-phenyl rings are 64.9?(2) and 64.6?(2)°, respectively. Inter-molecular C-H?O and C-H?F hydrogen bonds stabilize the three-dimensional supra-molecular architecture. Weak C-H?? and ?-? inter-actions [centroid-centroid distance = 3.877?(3)?Å] lead to a criss-cross mol-ecular packing along the c axis.

| S-EPMC3772451 | biostudies-literature

{2-[(1,3-Benzo-thia-zol-2-yl)meth-oxy]-5-chloro-phen-yl}(4-chloro-phen-yl)methan-one.

Project description:In the title compound, C21H13Cl2NO2S, the benzo-thia-zole ring makes dihedral angles of 0.94?(1) and 70.65?(5)° with the 4-chloro-phenyl-methanone unit and the 5-chloro-phenyl ring, respectively. The dihedral angle between the 4-chloro-phenyl-methanone unit and the 5-chloro-phenyl ring is 66.20?(5)°. The crystal structure consists of dimeric units generated by C-H?N hydrogen bonds, further linked by C-H?O and C-H?? inter-actions, leading to a three-dimensional network.

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[4-(4-Meth-oxy-phen-yl)-2-(pyridin-3-yl)-1,3-thia-zol-5-yl][4-(tri-fluoro-meth-yl)phen-yl]methanone.

Project description:In the title compound, C23H15F3N2O2S, the thia-zole ring makes dihedral angles of 12.98?(13), 49.30?(11) and 49.83?(12)° with the pyridine ring, the meth-oxy-phenyl ring and the (tri-fluoro-meth-yl)phenyl ring, respectively. In the crystal, mol-ecules are connected via C-H?O hydrogen bonds, forming chains along [010]. There are also C-H?? and C-F?? inter-actions present, forming a three-dimensional structure.

| S-EPMC3884424 | biostudies-literature

3-(4-Meth-oxy-phen-yl)-1,3-selenazolo[2,3-b][1,3]benzo-thia-zol-4-ium hydrogen sulfate.

Project description:The title compound, C16H12NOSSe(+)·HSO4 (-), was obtained from a mixture of 3-(4-meth-oxy-phen-yl)[1,3]selenazolo[2,3-b][1,3]benzo-thia-zol-4-ium chloride and potassium hydrogen sulfate. In the cation, the benzene ring is twisted by 71.62?(7)° from the tricycle mean plane. In the crystal, O-H?O hydrogen bonds link the anions into chains along [100]. The anions in adjacent chains are linked via weak C-H?O hydrogen bonds. The crystal packing exhibits short inter-molecular contacts between the chalcogen unit and the O atoms: Se?O(anion) 2.713?(3), Se?O(cation) 2.987?(3) and S?O(anion) 2.958?(3)?Å.

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N-(3-Meth-oxy-phen-yl)-4-{4-methyl-2-[(meth-yl)(4-methyl-phen-yl)amino]-1,3-thia-zol-5-yl}pyrimidin-2-amine.

Project description:The asymmetric unit of the title compound, C(23)H(23)N(5)OS, contains two independent mol-ecules. In one mol-ecule, the thia-zole and pyrimidine rings are almost co-planar, making a dihedral angle of 2.48?(8)°. In the other mol-ecule, the corresponding dihedral angle is 12.82?(8)°. The crystal structure is stabilized by weak inter-molecular N-H?N and C-H?O inter-actions that extend along the b axis.

| S-EPMC3051738 | biostudies-literature

(2-(Benzo[d]thia-zol-2yl-meth-oxy)-5-chloro-phen-yl)(phen-yl)methanone.

Project description:In the title compound, C(21)H(14)ClNO(2)S, the dihedral angle between the benzothia-zole and diphenyl methanone groups is 68.6?(2)°. The crystal structure consists of dimeric units generated by C-H?N bonds, further linked by C-H?O bonds and C-H?? and ?-? inter-actions [centroid-centroiddistance = 3.856?(2)?Å], which lead to a criss-cross assembly parallel to (001).

| S-EPMC3515230 | biostudies-literature

2-Isopropyl-2-(6-meth-oxy-1,3-benzo-thia-zol-2-yl)-5,5-dimethyl-1,3-thia-zolidin-4-one.

Project description:The title compound, C16H20N2O2S2, crystallizes with two enanti-omers (A and B) in the asymmetric unit. The most noticeable difference between these two mol-ecules is the relative orientation of the benzo-thia-zole rings, with S-C-C-S torsion angles of -19.4?(2) (mol-ecule A) and 100.6?(1)° (mol-ecule B). The amide structure of the thia-zolidinone rings leads to inter-molecular hydrogen-bonded dimers of the R and S enanti-omers.

| S-EPMC3884408 | biostudies-literature

2-[(1,3-Benzo-thia-zol-2-yl)imino-meth-yl]-6-meth-oxy-phenol: a new monoclinic polymorph.

Project description:The title compound, C15H12N2O2S, is a P21/c polymorph of a previously reported P21/n polymorph [Büyükgüngör et al. (2004 ?). Acta Cryst. E60, o1414-o1416]. The dihedral angle between the benzo-thia-zole (r.m.s. deviation = 0.010?Å) and the benzene ring of 7.86?(6)° compares with 10.76?(10)° in the literature structure. The meth-oxy substituent is almost coplanar with the benzene ring to which it is attached [C-O-C-C torsion angle = 178.31?(14)°] and the conformation about the imine bond [1.287?(2)?Å] is E. There is an intra-molecular O-H?N hydrogen bond and the hy-droxy O and thio-ether S atoms are syn. In the crystal, columns are formed along the b axis as centrosymmetric dimeric aggregates, mediated by C-H?O inter-actions and linked by ?-? inter-actions between the thia-zole and benzene rings [centroid-to-centroid distance = 3.8256?(10)?Å].

| S-EPMC3793768 | biostudies-literature

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