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Crystal structure of (2E)-N-methyl-2-[(4-oxo-4H-chromen-3-yl)methyl-idene]hydrazine-carbo-thio-amide.

ABSTRACT: In the title compound, C12H11N3O2S, the dihedral angle between the 4H-chromen-4-one ring system and the -CH=N-NH-CS-NH- unit is 6.22?(1)°. In the crystal, inversion dimers linked by pairs of N-H?O hydrogen bonds generate R 2 (2)(14) loops. The dimers are reinforced by a pair of C-H?O inter-actions, which generate R 2 (2)(10) loops.

SUBMITTER: Vimala G

PROVIDER: S-EPMC4257262 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature

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Crystal structure of (2E)-N-methyl-2-[(4-oxo-4H-chromen-3-yl)methyl-idene]hydrazine-carbo-thio-amide.

Vimala G G Govindaraj J J Haribabu J J Karvembu R R SubbiahPandi A A

Acta crystallographica. Section E, Structure reports online 20141008 Pt 11

In the title compound, C12H11N3O2S, the dihedral angle between the 4H-chromen-4-one ring system and the -CH=N-NH-CS-NH- unit is 6.22 (1)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(14) loops. The dimers are reinforced by a pair of C-H⋯O inter-actions, which generate R 2 (2)(10) loops. ...[more]

PMID: 25484795

Similar Datasets

Crystal structures of two hydrazinecarbo-thio-amide derivatives: (E)-N-ethyl-2-[(4-oxo-4H-chromen-3-yl)methyl-idene]hydrazinecarbo-thio-amide hemi-hydrate and (E)-2-[(4-chloro-2H-chromen-3-yl)methyl-idene]-N-phenyl-hydrazinecarbo-thio-amide.

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

2-Cyclo-heptyl-idene-N-phenyl-hydrazine-carbo-thio-amide.

Project description:In the title compound, C14H19N3S, the seven-membered cyclo-heptane ring adopts a chair conformation. An intra-molecular N-H⋯N hydrogen bond [graph-set motif S(5)] is present in the N-N-C-N chain between the ring systems. An intra-molecular C-H⋯S contact also occurs. In the crystal, pairs of mol-ecules form centrosymmetric dimers through N-H⋯S hydrogen bonds [graph-set R 2 (2)(8)]. These dimers are connected by C-H⋯S inter-actions with an R 2 (2)(14) motif.

| S-EPMC3998488 | biostudies-literature

Crystal structure of (E)-2-[(2S,5R)-2-isopropyl-5-methyl-cyclo-hexyl-idene]hydrazine-1-carbo-thio-amide.

Project description:The title compound, C11H21N3S, consists of a menthone moiety attached to an extended thio-semicarbazone group with the N-N-C-N torsion angle being 11.92 (16)°. The cyclo-hexane ring has a chair conformation and the conformation about the C=N bond is E. In the crystal, mol-ecules are linked via pairs of N-H⋯S hydrogen bonds, forming chains along the a axis. The absolute structure could be assigned with reference to the starting material, i.e. enanti-opure (-)-menthone [Flack parameter = 0.05 (5)].

| S-EPMC4186105 | biostudies-literature

(2E)-2-(5-Bromo-2-hy-droxy-3-meth-oxy-benzyl-idene)-N-phenyl-hydrazine-carbo-thio-amide.

Project description:The title compound, C(15)H(14)BrN(3)O(2)S, adopts an E,E conformation with respect to the azomethine and hydrazinic bonds and exists in the thio-amide form. The two rings in the mol-ecule are twisted away from each other, making a dihedral angle of 69.13?(13)°. In the crystal, mol-ecules are linked through pairs of N-H?O and O-H?S hydrogen bonds, leading to the formation of inversion dimers which are stacked along the a axis. Intra-molecular N-H?N, O-H?O and C-H?? inter-actions are also present.

| S-EPMC3379435 | biostudies-other

3-[(4-Oxo-4H-thio-chromen-3-yl)meth-yl]-4H-thio-chromen-4-one.

Project description:The title mol-ecule, C19H12S2O2, lies on a twofold rotation axis. The thio-chromonone unit is essentially planar, with a maximum deviation of 0.0491?(14)?Å. The dihedral angle between the thio-chromenone ring systems is 64.48?(4)°. In the crystal, there are weak ?-? stacking inter-actions, with a centroid-centroid distance of 3.7147?(9)?Å.

| S-EPMC3588462 | biostudies-literature

(E)-4-Methyl-N'-[(4-oxo-4H-chromen-3-yl)methyl-idene]benzohydrazide.

Project description:In the title chromone-tethered benzohydrazide derivative, C18H14N2O3, the 4H-chromen-4-one and the -CH=N-NH-CO- units are each essentially planar, with the largest deviations from thei planes being 0.052?(2) and 0.003?(2)?Å, respectively. The dihedral angles between the 4H-chromen-4-one and the -CH=N-NH-CO- units, the 4H-chromen-4-one unit and the benzene ring of the 4-tolyl group, and the benzene ring of the 4-tolyl group and the -CH=N-NH-CO- unit are 8.09?(7), 9.94?(5) and 17.97?(8)°, respectively. In the crystal, the mol-ecules form two types of centrosymmetric dimers: one by N-H?O hydrogen bonds and the other by ?-? stacking inter-actions between the 4H-chromen-4-one unit and the 4-tolyl group [centroid-centroid distance = 3.641?(5)?Å]. These dimers form one-dimensional assemblies extending along the a-axis direction. Additional ?-? stacking inter-actions between two 4H-chromen-4-one units [centroid-centroid distance = 3.591?(5)?Å] and two 4-tolyl groups [centroid-centroid distance = 3.792?(5)?Å] organize the mol-ecules into a three-dimensional network.

| S-EPMC4011241 | biostudies-literature

Crystal structure of (E)-2-[1-(benzo[d][1,3]dioxol-5-yl)ethyl-idene]-N-methyl-hydrazine-1-carbo-thio-amide.

Project description:In the title compound, C11H13N3O2S, there is a short intra-molecular N-H⋯N contact. The benzo[d][1,3]dioxole ring system is approximately planar (r.m.s. deviation = 0.025 Å) and makes a dihedral angle of 56.83 (6)° with the mean plane of the methyl-thio-semicarbazone fragment [-N-N-C(=S)-N-C; maximum deviation = 0.1111 (14) Å for the imino N atom]. In the crystal, mol-ecules are linked via pairs of N-H⋯S hydrogen bonds, forming inversion dimers. The dimers are connected by N-H⋯S hydrogen bonds into layers parallel to (100). The H atoms of both methyl groups are disordered over two sets of sites and were refined with occupancy ratios of 0.5:0.5 and 0.75:0.25.

| S-EPMC4331916 | biostudies-literature

Crystal structure of (7-methyl-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbo-di-thio-ate.

Project description:In the title compound, C17H19NO2S2, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.0383 (28) Å, and the piperidine ring adopts a chair conformation. The 2H-chromene ring makes dihedral angles of 32.89 (16) and 67.33 (8)°, respectively, with the mean planes of the piperidine ring and the carbodi-thio-ate group. In the crystal, C-H⋯O and weak C-H⋯S hydrogen bonds link the mol-ecules into chains along [001]. The crystal structure also features C-H⋯π and π-π inter-actions, with a centroid-centroid distance of 3.7097 (17) Å.

| S-EPMC4571421 | biostudies-literature

Crystal structure of (<i>E</i>)-<i>N</i>-cyclo-hexyl-2-(2-hy-droxy-3-methyl-benzyl-idene)hydrazine-1-carbo-thio-amide.

Project description:The asymmetric unit of the title compound, C15H21N3OS, comprises of two crystallographically independent mol-ecules (A and B). Each mol-ecule consists of a cyclo-hexane ring and a 2-hy-droxy-3-methyl-benzyl-idene ring bridged by a hydrazinecarbo-thio-amine unit. Both mol-ecules exhibit an E configuration with respect to the azomethine C=N bond. There is an intra-molecular O-H?N hydrogen bond in each mol-ecule forming an S(6) ring motif. The cyclo-hexane ring in each mol-ecule has a chair conformation. The benzene ring is inclined to the mean plane of the cyclo-hexane ring by 47.75?(9)° in mol-ecule A and 66.99?(9)° in mol-ecule B. The mean plane of the cyclo-hexane ring is inclined to the mean plane of the thio-urea moiety [N-C(=S)-N] by 55.69?(9) and 58.50?(8)° in mol-ecules A and B, respectively. In the crystal, the A and B mol-ecules are linked by N-H?S hydrogen bonds, forming 'dimers'. The A mol-ecules are further linked by a C-H?? inter-action, hence linking the A-B units to form ribbons propagating along the b-axis direction. The conformation of a number of related cyclo-hexa-nehydrazinecarbo-thio-amides are compared to that of the title compound.

| S-EPMC6659332 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-2-(5-bromo-2-hy-droxy-benzyl-idene)hydrazine-carbo-thio-amide di-methyl sulfoxide monosolvate.

Project description:The mol-ecule of the title Schiff base, C8H8BrN3OS·C2H6OS, which crystallizes as a di-methyl sulfoxide (DMSO) monosolvate, displays an E configuration with respect to the C=N bond, with a dihedral angle of 14.54 (11)° between the benzene ring and the mean plane of the N-N-C(N)=S unit. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains propagating along the b-axis direction. Within the chains there are R23(11) ring motifs, which are reinforced by C-H⋯ODMSO hydrogen bonds enclosing secondary R12(6) and R23(9) loops. The chains are linked by O-Hhydrox-yl⋯S hydrogen bonds, forming layers parallel to (011). Inversion-related layers are linked by short Br⋯Br inter-actions [3.5585 (5) Å], forming slabs parallel to (011). The inter-molecular inter-actions have been investigated using Hirshfeld surface studies and two-dimensional fingerprint plots. The crystal structure of the unsolvated form of the title compound has been reported previously [Kargar et al. (2010). Acta Cryst. E66, o2999], and its solid-state structure is compared with that of the title solvated form.

| S-EPMC5956319 | biostudies-literature

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