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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.

ABSTRACT: 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].

SUBMITTER: Fun HK

PROVIDER: S-EPMC3089094 | biostudies-literature | 2011 May

REPOSITORIES: biostudies-literature

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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.

Fun Hoong-Kun HK Loh Wan-Sin WS Nithinchandra Kalluraya Balakrishna B

Acta crystallographica. Section E, Structure reports online 20110422 Pt 5

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 l ...[more]

PMID: 21754481

Similar Datasets

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

Project description:The title compound, C(19)H(15)ClN(6)O(3)S, exists in trans and cis configurations with respect to the acyclic C=N bonds. The 3,6-dihydro-2H-1,3,4-thia-diazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.013 (1) Å] and forms dihedral angles of 34.76 (4) and 48.67 (4)° with the benzene rings. An intra-molecular C-H⋯O hydrogen bond stabilizes the mol-ecular structure and forms an S(6) ring motif. In the crystal packing, inter-molecular N-H⋯N hydrogen bonds link centrosymmetrically related mol-ecules into dimers, generating R(2) (2)(8) ring motifs. The dimers are then linked into a three-dimensional network by inter-molecular C-H⋯O and C-H⋯Cl hydrogen bonds, and by C-H⋯π inter-actions. Further stabilization is provided by π-π inter-actions involving the sydnone rings, with centroid-centroid separations of 3.4198 (5) Å.

| S-EPMC3089192 | biostudies-literature

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.

| S-EPMC3099954 | biostudies-literature

4-{(Z)-2-[(E)-Benzyl-idenehydrazinyl-idene]-3,6-dihydro-2H-1,3,4-thia-diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate.

Project description:The title compound, C(18)H(14)N(6)O(2)S, exists in trans and cis configurations with respect to the two acyclic C=N bonds [bond lengths = 1.2835 (9) and 1.3049 (9) Å]. 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 53.70 (4) and 60.26 (4)° with the two phenyl rings. In the crystal, mol-ecules are linked via pairs of inter-molecular N-H⋯N hydrogen bonds, generating R(2) (2)(8) ring motifs, and are further linked via inter-molecular C-H⋯O and C-H⋯S hydrogen bonds into a three-dimensional network. The short inter-molecular distance between the oxadiazol-3-ium rings [3.4154 (4) Å] indicates the existence of a π-π inter-action.

| S-EPMC3100016 | biostudies-literature

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.

Project description: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⋯π inter-actions.

| S-EPMC2979609 | biostudies-literature

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.

| S-EPMC3007576 | biostudies-literature

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.

Project description:In the title triazolothia-diazine derivative, C(20)H(16)N(6)O(3)S {systematic name: 3-(4-methyl-phen-yl)-4-[3-(phen-oxy-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}, an S(6) ring motif is generated by an intra-molecular C-H⋯O hydrogen bond. The 3,6-dihydro-1,3,4-thia-diazine ring adopts a twist-boat conformation. The dihedral angle between the 1,2,3-oxadiazole and 1,2,4-triazole rings is 46.45 (14)°. The 1,2,3-oxadiazole ring is inclined at dihedral angle of 59.49 (13)° with respect to the benzene ring attached to it. In the crystal structure, inter-molecular C-H⋯O and C-H⋯N hydrogen bonds link neighbouring mol-ecules into two-mol-ecule-thick arrays parallel to the bc plane. A short S⋯O inter-action [2.9565 (19) Å] also occurs.

| S-EPMC3007409 | biostudies-literature

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⋯π inter-actions. An intra-molecular C-H⋯O hydrogen bond is also observed, which generates an S(6) ring motif.

| S-EPMC3099773 | biostudies-literature

4-[(2E)-2-(4-Chloro-benzyl-idene)hydrazinyl-idene]-1-methyl-1,4-dihydro-pyridine monohydrate.

Project description:In the title compound, C(13)H(12)ClN(3)·H(2)O, the organic mol-ecule is almost planar, with a dihedral angle of 3.22 (10)° between the benzene and pyridine rings. The crystal structure is stabilized by O-H⋯N and C-H⋯O hydrogen bonding and π-π stacking inter-actions [centroid-centroid distances = 3.630 (1) and 3.701 (1) Å].

| S-EPMC2979526 | biostudies-literature

5-({[(E)-Benzyl-idene-amino]-oxy}meth-yl)-1,3,4-thia-diazol-2-amine.

Project description:In the mol-ecule of the title compound, C(10)H(10)N(4)OS, the configuration about the C=N double bond is E. The dihedral angle between the thia-diazole and benzene rings is 81.1 (1)°. In the crystal, mol-ecules are linked by N-H⋯N and C-H⋯O hydrogen bonds to form a two-dimensional network parallel with the bc plane.

| S-EPMC3295532 | biostudies-literature

(2E)-2-Benzyl-idene-4-ethyl-3,4-dihydro-naphthalen-1(2H)-one.

Project description:In the title compound, C(19)H(18)O, the exocyclic C=C double bond has an E configuration. The ethyl substituent on the cyclo-hexa-none ring is in an axial position. The cyclo-hexa-none ring adopts a half-chair conformation, presumably due to conjugation in the benzene ring.

| S-EPMC3151853 | biostudies-literature

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