Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure of (Z)-2-(5-fluoro-2-oxoindolin-3-yl-idene)hydrazinecarbo-thio-amide.

ABSTRACT: 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.

SUBMITTER: Bittencourt VC

PROVIDER: S-EPMC4459295 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure of (Z)-2-(5-fluoro-2-oxoindolin-3-yl-idene)hydrazinecarbo-thio-amide.

Bittencourt Viviane C D VC Almeida Vitor Y G VY Back Davi F DF Gervini Vanessa C VC de Oliveira Adriano Bof AB

Acta crystallographica. Section E, Crystallographic communications 20150509 Pt 6

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) plan ...[more]

PMID: 26090179

Similar Datasets

2-(5-Chloro-2-oxoindolin-3-yl-idene)hydrazinecarbo-thio-amide.

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 ?-? stacking inter-actions [centroid-centroid distance = 3.849?(2)?Å].

| S-EPMC4029216 | biostudies-literature

2-(5-Iodo-2-oxoindolin-3-yl-idene)hydrazinecarbo-thio-amide including an unknown solvate.

Project description:The mol-ecule of the title compound, C9H7IN4OS, is almost planar (r.m.s. deviation = 0.0373 Å). In the mol-ecule, N-H⋯N and N-H⋯O hydrogen bonds generate, respectively, S(5) and S(6) ring motifs. In the crystal, mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains propagating along [010]. These chains are linked via S⋯I contacts [3.4915 (16) Å], forming sheets lying parallel to (100). A region of disordered electron density, probably a disordered tetra-hydro-furan solvent mol-ecule, was treated using the SQUEEZE routine in PLATON [Spek (2009). Acta Cryst. D65, 148-155]. The formula mass and unit-cell characteristics were not taken into account during refinement.

| S-EPMC4051098 | biostudies-literature

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 ?-? [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?? inter-actions, forming ribbons lying parallel to (210).

| S-EPMC4350706 | biostudies-literature

Crystal structure of <i>N</i>-ethyl-2-(1,2,3,4-tetra-hydro-naphthalen-1-yl-idene)hydrazinecarbo-thio-amide.

Project description:There are two crystallographically independent mol-ecules in the asymmetric unit of the title compound, C13H17N3S, one of them being disordered over the methyl group [site-occupancy ratio = 0.705?(5):0.295?(5)]. The maximum r.m.s. deviations from the mean plane of the non-H atoms for the tetra-lone fragments amount to 0.4572?(17) and 0.4558?(15)?Å. The N-N-C-N fragments are not planar and torsion angles are -9.4?(2) and 8.3?(2)°. In the crystal, the mol-ecules are linked by weak N-H?S inter-actions into chains along [100] with graph-set motif C(4) and connected by weak N-H?S and C-H?S inter-actions, forming R21(10) rings. The Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H?H (64.20%), H?S (12.60%) and H?C (12.00%) inter-actions. The crystal packing resembles a herringbone arrangement when viewed along [001].

| S-EPMC5290584 | biostudies-literature

Crystal structure of (E)-2-[(4-chloro-2H-chromen-3-yl)methyl-idene]-N-cyclo-hexyl-hydrazinecarbo-thio-amide.

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

Crystal structure of (Z)-2-(1-benzyl-2-oxoindolin-3-yl-idene)-N-phenyl-hydra-zine-1-carbo-thio-amide.

Project description:The title compound, C22H18N4OS, crystallized with four independent mol-ecules (A, B, C and D) in the asymmetric unit. All four mol-ecules have a Z conformation about the C=N bond with the benzyl ring being inclined to the indoline ring mean planes by 73.4?(2), 77.9?(2), 73.2?(2) and 77.2?(2)° in mol-ecules A, B, C and D, respectively. In mol-ecules A and B, the phenyl ring is inclined to the mean plane of the indoline ring mean plane by 12.0?(2) and 12.2?(2)°, respectively. However, in mol-ecules C and D, the same dihedral angles are larger, viz. 37.3?(2) and 36.4?(2)°, respectively. Consequently, the benzyl and phenyl rings are almost normal to one another in mol-ecules A and B [dihedral angles = 80.3?(3) and 87.1?(3)°, respectively], while in mol-ecules C and D, the same dihedral angles are only 48.8?(2) and 43.8?(3)°, respectively. There is an intra-molecular N-H?O hydrogen bond in each mol-ecule with an S(6) ring motif. There are also short intra-molecular N-H?N and C-H?S contacts in each mol-ecule. In the crystal, mol-ecules are linked via C-H?S hydrogen bonds and C-H?? inter-actions, forming a three-dimensional structure. The crystal was refined as a non-merohedral twin with a final BASF value of 0.110?(1).

| S-EPMC4350691 | biostudies-literature

(E)-2-[(1H-Imidazol-4-yl)methyl-idene]hydrazinecarbo-thio-amide monohydrate.

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

4-(3-Fluoro-phen-yl)-1-(2-oxoindolin-3-yl-idene)thio-semicarbazide.

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 ?-? inter-actions [centroid-centroid distances in the range 3.520?(2)-3.820?(9)?Å].

| S-EPMC2983261 | biostudies-literature

(Z)-2-(5-Fluoro-2-oxoindolin-3-yl-idene)-N-phenyl-hydrazinecarbothio-amide.

Project description:The title compound, C(15)H(11)FN(4)OS, crystallizes with three independent mol-ecules (A, B and C) in the asymmetric unit. The dihedral angles between the nine-membered 5-fluoro-indolin-2-one ring system and the benzene ring are 22.14 (11), 12.56 (11) and 3.70 (11)° in mol-ecules A, B and C, respectively. In all three mol-ecules, intra-molecular cyclic N-H⋯O and C-H⋯S hydrogen-bonding inter-actions [graph set S(6)] are present in the N-N-C-N chain between the ring systems. In the crystal, the A mol-ecules form centrosymmetric cyclic dimers through inter-molecular N-H⋯O hydrogen bonds, which are linked into a supramolecular chain along [100] via C-H⋯F interactions; each type of hydrogen bond has graph set graph set R(2) (2)(8). A similar chain stabilised by similar interactions and also along [100] but, comprising alternating molecules of B and C is found. The latter chains are connected via C-H⋯S interactions, forming a layer with a zigzag topology parallel to (001).

| S-EPMC3274981 | biostudies-literature

Hirshfeld analysis and mol-ecular docking with the RDR enzyme of 2-(5-chloro-2-oxoindolin-3-yl-idene)-N-methyl-hydrazinecarbo-thio-amide.

Project description:The acetic acid-catalyzed reaction between 5-chloro-isatin and 4-methyl-thio-semicarbazide yields the title compound, C10H9ClN4OS (I) (common name: 5-chloro-isatin-4-methyl-thio-semicarbazone). The mol-ecule is nearly planar (r.m.s. deviation = 0.047?Å for all non-H atoms), with a maximum deviation of 0.089?(1)?Å for the O atom. An S(6) ring motif formed by an intra-molecular N-H?O hydrogen bond is observed. In the crystal, mol-ecules are linked by N-H?O hydrogen bonds, forming chains propagating along the a-axis direction. The chains are linked by N-H?S hydrogen bonds, forming a three-dimensional supra-molecular structure. The three-dimensional framework is reinforced by C-H?? inter-actions. The absolute structure of the mol-ecule in the crystal was determined by resonant scattering [Flack parameter = 0.006?(9)]. The crystal structure of the same compound, measured at 100?K, has been reported on previously [Qasem Ali et al. (2012 ?). Acta Cryst. E68, o964-o965]. The Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H?H (23.1%), H?C (18.4%), H?Cl (13.7%), H?S (12.0%) and H?O (11.3%) inter-actions. A mol-ecular docking evaluation of the title compound with the ribonucleoside diphosphate reductase (RDR) enzyme was carried out. The title compound (I) and the active site of the selected enzyme show Cl?H-C(LYS140), Cg(aromatic ring)?H-C(SER71), H?O-C(GLU200) and FeIII?O?FeIII inter-molecular inter-actions, which suggests a solid theoretical structure-activity relationship.

| S-EPMC5418788 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data