4-Fluorobenzyl (Z)-2-(2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate
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ABSTRACT:
SUBMITTER: Abdul Manan M
PROVIDER: S-EPMC10993559 | biostudies-literature | 2024 Mar
REPOSITORIES: biostudies-literature
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Project description:The title compound, C17H18N2O2S2, synthesized via a condensation reaction between S-benzyl di-thio-carbazate and 3,4-di-meth-oxy-benzaldehyde, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. Both mol-ecules have an L-shape but differ in the orientation of the benzyl ring with respect to the 3,4-di-meth-oxy-benzyl-idine ring, this dihedral angle is 65.59 (8)° in mol-ecule A and 73.10 (8)° in mol-ecule B. In the crystal, the A and B mol-ecules are linked via pairs of N-H⋯S hydrogen bonds, forming dimers with an R 2 (2)(8) ring motif. The dimers are linked via pairs of C-H⋯O hydrogen bonds, giving inversion dimers of dimers. These units are linked by C-H⋯π inter-actions, forming ribbons propagating in the [100] direction.
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Project description:In the title hydrazinecarbodi-thio-ate derivative, C27H26N2O2S2, the asymmetric unit is comprised of four mol-ecules (Z = 8 and Z' = 4). The 4-meth-oxy-phenyl rings are slightly twisted away from their attached olefinic double bonds [torsion angles = 5.9 (4)-19.6 (4)°]. The azomethine double bond has an s-trans configuration relative to one of the C=C bonds and an s-cis configuration relative to the other [C=C-C= N = 147.4 (6)-175.7 (2) and 15.3 (3)-37.4 (7)°, respectively]. The torsion angles between the azomethine C=N double bond and hydrazine-1-carbodi-thio-ate moiety indicate only small deviations from planarity, with torsion angles ranging from 0.9 (3) to 6.9 (3)° and from 174.9 (3) to 179.7 (2)°, respectively. The benzyl ring and the methyl-enesulfanyl moiety are almost perpendicular to each other, as indicated by their torsion angles [range 93.7 (3)-114.6 (2)°]. In the crystal, mol-ecules are linked by C-H⋯O, N-H⋯S and C-H⋯π(ring) hydrogen-bonding inter-actions into a three-dimensional network. Structural details of related benzyl hydrazine-1-carbodi-thio-ate are surveyed and compared with those of the title compound.
| S-EPMC6829705 | biostudies-literature
Project description:The title compound, C17H15N3OS2 was obtained from the condensation reaction of S-benzyl-dithio-carbazate and 5-methyl-isatin. In the solid-state, the mol-ecule adopts a Z configuration with the 5-methyl-isatin and di-thio-carbazate groups located on the same side of the C=N bond, involving an intra-molecular N-H⋯O hydrogen bond.
| S-EPMC10561232 | biostudies-literature
Project description:In the title compound, C(15)H(11)FN(4)OS, there are three independent mol-ecules, each with a disordered 3-fluoro-phenyl group [occupancy ratios = 0.547 (17):0.453 (17), 0.645 (5):0.355 (5) and 0.626 (15):0.374 (15)] and displaying dihedral angles of 4.2 (3), 25.2 (6) and 32.4 (5)° between the 2-oxoindoline and fluoro-substituted phenyl rings. Strong intra-molecular N-H⋯N and N-H⋯O and weak intra-molecular C-H⋯S hydrogen bonds complete S(5) and S(6) ring motifs, while strong inter-molecular N-H⋯O hydrogen bonds inter-connect the three independent mol-ecules through R(3) (3)(12) ring motifs. The three-mol-ecule units are in turn linked into polymeric sheets via C-H⋯F and C-H⋯S hydrogen bonds and π-π inter-actions [centroid-centroid distances in the range 3.520 (2)-3.820 (9) Å].
| S-EPMC2983261 | biostudies-literature
Project description:The title compound, C(15)H(11)FN(4)OS, is almost planar, the dihedral angle between the aromatic ring systems being 5.00 (13)°. The conformation is stabilized by intra-molecular N-H⋯N and N-H⋯O hydrogen bonds, which generate S(5) and S(6) rings, respectively. N-H⋯F and C-H⋯S inter-actions also occur. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur, generating R(2) (2)(8) loops.
| S-EPMC2979150 | biostudies-literature
Project description:In the title compound, C(16)H(11)F(3)N(4)OS, the dihedral angle between the aromatic ring systems is 69.15 (10)°. Intra-molecular N-H⋯N and N-H⋯O hydrogen bonds generate S(5) and S(6) rings, respectively. A short N-H⋯F contact also occurs. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops. The dimers are linked by N-H⋯F hydrogen bonds, forming polymeric chains propagating in [100]. π-π inter-actions also exist between the centroids of the benzene rings of the 2-oxoindoline group at a distance of 3.543 (3) Å and a short C=O⋯π contact occurs. Two F atoms of the trifluoro-methyl group are disordered over two sets of sites in a 0.517 (8):0.483 (8) ratio.
| S-EPMC3007868 | biostudies-literature
Project description:In the title compound, C(13)H(9)FN(4)O(4), the dihedral angle between the mean planes of the two benzene rings of the nearly planar mol-ecule is 6.6 (9)°. The dihedral angles between the mean planes of the benzene ring and its two attached nitro groups are 6.7 (7) and 7.2 (9)°. Crystal packing is stabilized by N-H⋯O hydrogen bonds, weak C-H⋯O and C-H⋯F inter-molecular inter-actions and centroid-centroid π-ring stacking inter-actions.
| S-EPMC3089184 | biostudies-literature
Project description:In the title compound, C(22)H(17)NO(5)S(2), the dithiole and oxindole rings are almost coplanar [dihedral angle = 2.71 (8)°] and the phenyl ring makes a dihedral angle of 73.65 (5)° with the oxindole ring. Inter-molecular π-π contacts between adjacent oxindole and dithiole rings [centroid-centroid distance = 3.7273 (11) Å] stabilize the crystal packing.
| S-EPMC3051557 | biostudies-literature
Project description:The title compound, C10H8BrN3OS2, a brominated di-thio-carbazate imine deriv-ative, was obtained from the condensation reaction of S-methyl-dithio-carbazate (SMDTC) and 5-bromo-isatin. The essentially planar mol-ecule exhibits a Z configuration, with the di-thio-carbazate and 5-bromo-isatin fragments located on the same sides of the C=N azomethine bond, which allows for the formation of an intra-molecular N-H⋯Ob (b = bromo-isatin) hydrogen bond generating an S(6) ring motif. In the crystal, adjacent mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming dimers characterized by an R 2 2(8) loop motif. In the extended structure, mol-ecules are linked into a three-dimensional network by C-H⋯S and C-H⋯Br hydrogen bonds, C-Br⋯S halogen bonds and aromatic π-π stacking.
| S-EPMC11375598 | biostudies-literature
Project description:In the title compound, C9H7FN4OS, the mol-ecules are almost planar, with an r.m.s. deviation of 0.047 (3) Å from the mean plane defined by the non-H atoms and a maximum deviation of 0.123 (2) Å for the amine N atom. The torsion angle for the N-N-C-S unit is 176.57 (19)°. In the crystal, mol-ecules are linked into inversion dimers via pairs of N-H⋯F hydrogen bonds and, additionally, through N-H⋯O and N-H⋯S hydrogen bonds, building a two-dimensional hydrogen-bond network parallel to the (103) plane. An intra-molecular N-H⋯O inter-action is also observed.
| S-EPMC4459295 | biostudies-literature