N-Methyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide
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ABSTRACT:
SUBMITTER: de Oliveira A
PROVIDER: S-EPMC10842277 | biostudies-literature | 2024 Jan
REPOSITORIES: biostudies-literature
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Project description:A second crystalline modification of the title compound, C12H19N3S [common name: cis-jasmone thio-semicarbazone] was crystallized from tetra-hydro-furane at room temperature. There is one crystallographic independent mol-ecule in the asymmetric unit, showing disorder in the cis-jasmone chain [site-occupancy ratio = 0.590 (14):0.410 (14)]. The thio-semicarbazone entity is approximately planar, with the maximum deviation from the mean plane through the N/N/C/S/N atoms being 0.0463 (14) Å [r.m.s.d. = 0.0324 Å], while for the five-membered ring of the jasmone fragment, the maximum deviation from the mean plane through the carbon atoms amounts to 0.0465 (15) Å [r.m.s.d. = 0.0338 Å]. The mol-ecule is not planar due to the dihedral angle between these two fragments, which is 8.93 (1)°, and due to the sp 3-hybridized carbon atoms in the jasmone fragment chain. In the crystal, the mol-ecules are connected by N-H⋯S and C-H⋯S inter-actions, with graph-set motifs R 2 2(8) and R 2 1(7), building mono-periodic hydrogen-bonded ribbons along [010]. A Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are H⋯H (67.8%), H⋯S/S⋯H (15.0%), H⋯C/C⋯H (8.5%) and H⋯N/N⋯H (5.6%) [only non-disordered atoms and those with the highest s.o.f. were considered]. This work reports the second crystalline modification of the cis-jasmone thio-semicarbazone structure, the first one being published recently [Orsoni et al. (2020 ▸). Int. J. Mol. Sci. 21, 8681-8697] with the crystals obtained in ethanol at 273 K.
| S-EPMC10833130 | biostudies-literature
Project description:The hydro-chloric acid-catalyzed equimolar reaction between cis-jasmone and 4-phenyl-thio-semicarbazide yielded the title compound, C18H23N3S (common name: cis-jasmone 4-phenyl-thio-semicarbazone). Concerning the hydrogen bonding, an N-H⋯N intra-molecular inter-action is observed, forming a ring with graph-set motif S(5). In the crystal, the mol-ecules are connected into centrosymmetric dimers by pairs of N-H⋯S and C-H⋯S inter-actions, forming rings of graph-set motifs R 2 2(8) and R 2 1(7), with the sulfur atoms acting as double acceptors. The thio-semicarbazone entity is approximately planar, with the maximum deviation from the mean plane through the N/N/C/S/N atoms being 0.0376 (9) Å (the r.m.s.d. amounts to 0.0234 Å). The mol-ecule is substantially twisted as indicated by the dihedral angle between the thio-semicarbazone fragment and the phenyl ring, which amounts to 56.1 (5)°, and because of the jasmone fragment, which bears a chain with sp 3-hybridized carbon atoms in the structure. The Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are: H⋯H (65.3%), H⋯C/C⋯H (16.2%), H⋯S/S⋯H (10.9%) and H⋯N/N⋯H (5.5%).
| S-EPMC10833128 | biostudies-literature
Project description:In the title compound, C12H15N3S, the mol-ecule deviates slightly from planarity, with a maximum deviation from the mean plane of the non-H atoms of 0.2756 (6) Å for the S atom and a torsion angle for the N-N-C-N fragment of -7.04 (16)°. In the crystal, mol-ecules are linked by N-H⋯S hydrogen-bond inter-actions, forming centrosymmetric dimers. Additionally, one weak intra-molecular N-H⋯N hydrogen-bond inter-action is observed. The crystal packing shows a herringbone arrangement viewed along the c axis.
| S-EPMC4120594 | biostudies-literature
Project description:In the title compound, C5H7N5S·H2O, the main mol-ecule is approximately planar, with a maximum deviation from the mean plane through the non-H atoms of 0.1478 (12) Å for the amine N atom. In the crystal, the components are connected via N-H⋯O, N-H⋯S and O-H⋯N hydrogen bonds, forming a three-dimensional network.
| S-EPMC3884473 | biostudies-literature
Project description:The title compounds, C13H13N3O2S·0.5H2O, (I), and C17H14ClN3OS, (II), are hydrazinecarbo-thio-amide derivatives. Compound (I) crystallizes with two independent mol-ecules (A and B) and a water mol-ecule of crystallization in the asymmetric unit. The chromene moiety is essentially planar in mol-ecules A and B, with maximum deviations of 0.028 (3) and 0.016 (3) Å, respectively, for the carbonyl C atoms. In (II), the pyran ring of the chromene moiety adopts a screw-boat conformation and the phenyl ring is inclined by 61.18 (9)° to its mean plane. In the crystal of (I), bifurcated N-H⋯O and C-H⋯O hydrogen bonds link the two independent mol-ecules forming A-B dimers with two R 2 (1)(6) ring motifs, and R 2 (2)(10) and R 2 (2)(14) ring motifs. In addition to these, the water mol-ecule forms tetra-furcated hydrogen bonds which alternately generate R 4 (4)(12) and R 6 (6)(22) graph-set ring motifs. There are also π-π [inter-centroid distances = 3.5648 (14) and 3.6825 (15) Å] inter-actions present, leading to the formation of columns along the c-axis direction. In the crystal of (II), mol-ecules are linked by pairs of N-H⋯S hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked by C-H⋯π inter-actions, forming ribbons lying parallel to (210).
| S-EPMC4350706 | biostudies-literature
Project description:In the title compound, C17H20ClN3OS, the mean plane of the central thio-urea core makes dihedral angles of 26.56 (9) and 47.62 (12)° with the mean planes of the chromene moiety and the cyclo-hexyl ring, respectively. The cyclo-hexyl ring adopts a chair conformation. The N-H atoms of the thio-urea unit adopt an anti conformation. The chromene group is positioned trans, whereas the cyclo-hexyl ring lies in the cis position to the thione S atom, with respect to the thio-urea C-N bond. In the crystal, mol-ecules are linked by N-H⋯S hydrogen bonds, forming inversion dimers enclosing R (2) 2(8) ring motifs. The dimers are linked by C-H⋯Cl hydrogen bonds, enclosing R (6) 6(44) ring motifs, forming sheets lying parallel to (010).
| S-EPMC4186115 | biostudies-literature
Project description:There are two independent mol-ecules in the asymmetric unit of the title compound, C12H15N3S, both of which display disorder of several C atoms in the N-bound ring (occupancy ratios of 0.75:0.25 in the first independent mol-ecule and 0.50:0.50 in the second) with the methyl H atoms also being disordered in the first mol-ecule (occupancy ratio of 0.70:0.30). The planes of the benzene ring and the N-N-C-N fragment make dihedral angles of 12.92 (14)° in the first independent mol-ecule and 7.60 (13)° in the second. In the crystal, mol-ecules are linked by weak N-H⋯S hydrogen bonds into chains along the a-axis direction. The crystal packing ressembles a herringbone arrangement.
| S-EPMC3998428 | biostudies-literature
Project description:In the title compound, [CdCl2(C13H12N4S)]·CH3OH, the coord-ination geometry of the Cd(II) ion is slightly distorted square-pyramidal, as indicated by the τ index of 0.36 (8). The S atom, two N atoms from the pyridyl-azomethine moiety and one of the Cl atoms comprise the basal plane, while the other Cl atom occupies the apical position. The hydrazinecarbo-thio-amide moiety adopts an E conformation with respect to the azomethine bond. The solvate mol-ecule in the crystal lattice plays a major role in inter-connecting adjacent mol-ecules by means of O-H⋯Cl and N-H⋯O hydrogen-bonding inter-actions. A supra-molecular three-dimensional architecture is sustained in terms of further N-H⋯Cl and C-H⋯Cl hydrogen-bonding inter-actions.
| S-EPMC4158520 | biostudies-literature
Project description:The title mol-ecule, C9H7ClN4OS, is almost planar, with an r.m.s. deviation of 0.034 (2) Å for the mean plane through all the non-H atoms. Intra-molecular N-H⋯O and N-H⋯N hydrogen bonds form S(6) and S(5) ring motifs, respectively. In the crystal, mol-ecules are assembled into inversion dimers through pairs of co-operative N-H⋯Cl inter-actions. These dimers are connected along the b axis by N-H⋯O and N-H⋯S hydrogen bonds, generating layers parallel to (103). The layers are further connected along the a axis into a three-dimensional network, through weak π-π stacking inter-actions [centroid-centroid distance = 3.849 (2) Å].
| S-EPMC4029216 | biostudies-literature
Project description:The title compound, C12H17N3OS, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the benzene ring and the hydrazinecarbo-thio-amide group are 6.9 (4) and 37.2 (5)° in mol-ecules A and B, respectively. An intra-molecular O-H⋯N hydrogen bond is observed in each mol-ecule. This serves to maintain an approximately planar conformation for mol-ecule A, but leaves a significant twist between these two groups in mol-ecule B. In the crystal, a weak N-H⋯S inter-action is observed, forming inversion dimers among the B mol-ecules and resulting in an R 2 (2)(8) motif. These dimers are further inter-connected by weak N-H⋯O and C-H⋯O inter-molecular inter-actions, forming chains along [011].
| S-EPMC4051077 | biostudies-literature