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4-[3-(1-Naphthyl-oxymeth-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl]-3-p-tolyl-sydnone.

ABSTRACT: In the title sydnone compound, C(24)H(18)N(6)O(3)S {systematic name: 4-[3-(1-naphthyl-oxymeth-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl]-3-p-tolyl-4,5-dihydro-1,2,3-oxadiazol-3-ium-5-olate} an intra-molecular C-H?O hydrogen bond generates an S(6) ring motif. The 3,6-dihydro-1,3,4-thia-diazine ring adopts a twist-boat conformation. The essentially planar 1,2,3-oxadiazole and 1,2,4-triazole rings [maximum deviations of 0.006?(1) and 0.008?(1)?Å, respectively] are inclined to one another at inter-planar angle of 44.11?(4)°. The naphthalene unit forms an inter-planar angle of 66.40?(4)° with the 1,2,4-triazole ring. In the crystal packing, pairs of inter-molecular C-H?O hydrogen bonds link adjacent mol-ecules into dimers incorporating R(2) (2)(12) ring motifs. Further stabilization is provided by weak C-H?? inter-actions.

SUBMITTER: Goh JH

PROVIDER: S-EPMC2979609 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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4-[3-(1-Naphthyl-oxymeth-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl]-3-p-tolyl-sydnone.

Goh Jia Hao JH Fun Hoong-Kun HK Nithinchandra Kalluraya B B

Acta crystallographica. Section E, Structure reports online 20100522 Pt 6

In the title sydnone compound, C(24)H(18)N(6)O(3)S {systematic name: 4-[3-(1-naphthyl-oxymeth-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl]-3-p-tolyl-4,5-dihydro-1,2,3-oxadiazol-3-ium-5-olate} an intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The 3,6-dihydro-1,3,4-thia-diazine ring adopts a twist-boat conformation. The essentially planar 1,2,3-oxadiazole and 1,2,4-triazole rings [maximum deviations of 0.006 (1) and 0.008 (1) Å, respectively] are inclined to one another ...[more]

PMID: 21579474

Similar Datasets

3-Phenyl-4-{3-[(p-tol-yloxy)meth-yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl}sydnone.

Project description:In the title compound (systematic name3-phenyl-4-{3-[(p-tol-yloxy)meth-yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl}-1,2,3-oxadiazol-3-ium-5-olate), C(20)H(16)N(6)O(3)S, an intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The 3,6-dihydro-1,3,4-thia-diazine ring adopts a twist-boat conformation. The 1,2,3-oxadiazole and 1,2,4-triazole rings are inclined to each other at an inter-planar angle of 44.13 (13)°. The phenyl ring makes an inter-planar angle of 67.40 (13)° with the attached 1,2,3-oxadiazole ring. In the crystal structure, adjacent mol-ecules are inter-connected into two-mol-ecule-thick arrays parallel to (100) via C-H⋯O and C-H⋯N hydrogen bonds. A short S⋯O contact [2.9512 (18) Å] is observed.

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4-[3-(Phen-oxy-meth-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl]-3-(p-tol-yl)sydnone.

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3-(p-Tol-yl)-4-{3-[(phenyl-amino)-meth-yl]-7H-[1,2,4]triazolo[3,4-b][1,3,4]thia-diazin-6-yl}sydnone.

Project description:In the title compound, C(20)H(17)N(7)O(2)S (systematic name: 3-(4-methyl-phen-yl)-4-{3-[(phenyl-amino)-meth-yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl}-1,2,3-oxadiazol-3-ium-5-olate), the 3,6-dihydro-2H-1,3,4-thia-diazine ring adopts a half-boat conformation. The oxadiazol-3-ium ring makes dihedral angles of 57.99?(6) and 54.48?(6)° with the phenyl and benzene rings, respectively, while the 1,2,4-triazole ring forms corresponding angles of 37.35?(6) and 73.89?(6)°. The dihedral angle between the oxadiazol-3-ium and 1,2,4-triazole rings is 21.12?(6)°. In the crystal, the mol-ecules are linked via inter-molecular N-H?O and C-H?N hydrogen bonds into a layer parallel to the (100) plane. The crystal structure is further consolidated by C-H?? inter-actions. An intra-molecular C-H?O hydrogen bond is also observed, which generates an S(6) ring motif.

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4-{3-[(2-Isopropyl-5-methyl-phen-oxy)meth-yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl}-3-(p-tol-yl)sydnone.

Project description:In the title triazolothia-diazin compound, C(24)H(24)N(6)O(3)S (systematic name: 4-{3-[(2-isopropyl-5-methyl-phen-oxy)meth-yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl}-3-(4-methyl-phen-yl)-1,2,3-oxadiazol-3-ium-5-olate), an intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The two terminal methyl groups of the isopropyl unit are disordered over two sets of positions in a 0.715 (4):0.285 (4) ratio. The mean planes formed through the major and minor disordered isopropyl units are inclined at inter-planar angles of 73.1 (4) and 86.6 (8)°, respectively, with the attached phenyl ring. The 3,6-dihydro-1,3,4-thia-diazine ring adopts a twist-boat conformation. The inter-planar angle formed between 1,2,3-oxadiazole and 1,2,4-triazole rings is 18.80 (11)°. In the crystal, neighbouring mol-ecules are linked into sheets lying parallel to the bc plane by C-H⋯N hydrogen bonds. Weak inter-molecular π-π inter-actions [centroid-centroid distances = 3.2935 (11) and 3.5590 (12) Å] further stabilize the crystal structure.

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2-(6-Phenyl-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-3-yl)-1,3-benzothia-zole.

Project description:In the title compound, C(17)H(11)N(5)S(2), the dihedral angles formed between the triazole ring and the benzene ring and the 1,3-benzothia-zole ring system are 8.67?(8) and 13.90?(9)°, respectively. The conformation of the triazolo-thia-diazin-3-yl fused ring system is a twisted half-chair. Overall, the mol-ecule adopts a flattened shape. Supra-molecular helical chains along the a axis sustained by C-H?N inter-actions are found in the crystal structure. These are linked via C-H?? contacts as well as ?-? [centroid-centroid distance = 3.5911?(12)?Å] inter-actions between the triazole and thia-zole rings.

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4-[2-(2-Benzyl-idene-hydrazin-ylidene)-3,6-dihydro-2H-1,3,4-thia-diazin-5-yl]-3-(4-meth-oxy-phen-yl)-sydnone.

Project description:In the title compound, C(19)H(16)N(6)O(3)S, the 3,6-dihydro-1,3,4-thia-diazine ring adopts a twist-boat conformation. The dihedral angle between the meth-oxy-substituted benzene ring and the oxadiazole ring is 71.91 (7)°. In the crystal structure, centrosymmetrically related mol-ecules are linked into dimers via pairs of inter-molecular N-H⋯N hydrogen bonds, generating R(2) (2)(8) ring motifs. There is an intra-molecular C-H⋯O hydrogen bond which generates an S(6) ring motif.

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4-{2-[2-(4-Chloro-benzyl-idene)hydrazinyl-idene]-3,6-dihydro-2H-1,3,4-thia-diazin-5-yl}-3-phenyl-sydnone.

Project description:The title compound, C(18)H(13)ClN(6)O(2)S, exists in trans and cis configurations with respect to the acyclic C=N bonds [C=N = 1.2837 (15) and 1.3000 (14) Å, respectively]. The 3,6-dihydro-2H-1,3,4-thia-diazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.002 (1) Å] and forms dihedral angles of 50.45 (7) and 61.21 (6)° with the aromatic rings. In the crystal, inter-molecular N-H⋯N, C-H⋯Cl and C-H⋯S hydrogen bonds link the mol-ecules into layers parallel to ab plane. The crystal packing is stabilized by C-H⋯π inter-actions and further consolidated by π-π inter-actions involving the phenyl rings [centroid-centroid distance = 3.6306 (7) Å].

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3-Ethyl-6-(4-fluoro-phen-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazine.

Project description:In the title compound, C(12)H(11)FN(4)S, the thia-diazine ring adopts a twist-boat conformation. The dihedral angle between the triazolothia-diazine system and the benzene ring is 10.54?(9)°. The crystal structure is characterized by C-H?N hydrogen bonds. The crystal packing also exhibits ?-? inter-actions, with a centroid-centroid distance of 3.6348?(15)?Å.

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6-(4-Bromo-phen-yl)-3-methyl-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazine.

Project description:In the title compound, C(11)H(9)BrN(4)S, the 1,2,4-triazole ring is essentially planar (r.m.s. deviation = 0.020?Å) and makes a dihedral angle of 29.1?(5)° with the bromo-benzene ring. The 3,6-dihydro-1,3,4-thia-diazine ring adopts a twist-boat conformation. In the crystal, mol-ecules are linked by C-H?N inter-actions into sheets lying parallel to the (010) plane. The same N atom accepts two such hydrogen bonds.

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(Z)-7-[2-(4-Bromo-phen-yl)hydrazin-1-yl-idene]-6-methyl-3-(pyridin-4-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazine.

Project description:In the asymmetric unit of the title compound, C(16)H(12)BrN(7)S, there are two crystallographically independent mol-ecules with similar conformations. Both mol-ecules are slightly twisted; the central 1,2,4-triazolo[3,4-b]-1,3,4-thia-diazine ring system makes dihedral angles of 9.65 (15) and 13.29 (15)° with the pyridine and benzene rings, respectively, in one mol-ecule, whereas the corresponding values in the other mol-ecule are 9.30 (15) and 4.84 (15)°. A weak intra-molecular C-H⋯N inter-action with an S(6) ring motif is observed in each mol-ecule. In the crystal, the independent mol-ecules are each linked through N-H⋯N hydrogen bonds and weak C-H⋯N interactions into ribbons along the c axis. The ribbons are further linked together by weak C-H⋯N, C-H⋯π and π-π [centroid-centroid distances = 3.572 (2)-3.884 (2) Å] inter-actions.

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