Browse
Submit Data
Databases
API
Help

Dataset Information

18 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure and Hirshfeld surface analysis of (E)-3-[(2,3-di-chloro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide.

ABSTRACT: In the cation of the title salt, C16H14Cl2N3S+·Br-, the central thia-zolidine ring adopts an envelope conformation. The phenyl ring is disordered over two sites with a refined occupancy ratio of 0.541 (9):0.459 (9). In the crystal, C-H⋯Br and N-H⋯Br hydrogen bonds link the components into a three-dimensional network with the cations and anions stacked along the b-axis direction. Weak C-H⋯π inter-actions, which only involve the minor disorder component of the ring, also contribute to the mol-ecular packing. In addition, there are also inversion-related Cl⋯Cl halogen bonds and C-Cl⋯π (ring) contacts. A Hirshfeld surface analysis was conducted to verify the contributions of the different inter-molecular inter-actions.

SUBMITTER: Akkurt M

PROVIDER: S-EPMC6072981 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Crystal structure and Hirshfeld surface analysis of (E)-3-[(4-chloro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide.

Project description:The title salt, C16H15ClN3S+·Br-, is isotypic with (E)-3-[(4-fluoro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide [Khalilov et al. (2019 ▸). Acta Cryst. E75, 662-666]. In the cation of the title salt, the atoms of the phenyl ring attached to the central thia-zolidine ring and the atom joining the thia-zolidine ring to the benzene ring are disordered over two sets of sites with occupancies of 0.570 (3) and 0.430 (3). The major and minor components of the disordered thia-zolidine ring adopt slightly distorted envelope conformations, with the C atom bearing the phenyl ring as the flap atom. In the crystal, centrosymmetrically related cations and anions are linked into dimeric units via N-H⋯Br hydrogen bonds, which are further connected by weak C-H⋯Br contacts into chains parallel to the a axis. Furthermore, not existing in the earlier report of (E)-3-[(4-fluoro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide, C-H⋯π inter-actions and π-π stacking inter-actions [centroid-to-centroid distance = 3.897 (2) Å] between the major components of the disordered phenyl ring contribute to the stabilization of the mol-ecular packing. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions for the crystal packing are from H⋯H (30.5%), Br⋯H/H⋯Br (21.2%), C⋯H/H⋯C (19.2%), Cl⋯H/H⋯Cl (13.0%) and S⋯H/H⋯S (5.0%) inter-actions.

| S-EPMC6690452 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-3-(benzyl-idene-amino)-5-phenyl-thia-zolidin-2-iminium bromide.

Project description:The central thia-zolidine ring of the title salt, C16H16N3S+·Br-, adopts an envelope conformation, with the C atom bearing the phenyl ring as the flap atom. In the crystal, the cations and anions are linked by N-H?Br hydrogen bonds, forming chains parallel to the b-axis direction. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H?H (46.4%), C?H/H?C (18.6%) and H?Br/Br?H (17.5%) inter-actions.

| S-EPMC7057372 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-3-[(4-fluoro-benzyl-idene)amino]-5-phenyl-thia-zolidin-2-iminium bromide.

Project description:In the cation of the title salt, C16H15FN3S+·Br-, the phenyl ring is disordered over two sets of sites with a refined occupancy ratio of 0.503 (4):0.497 (4). The mean plane of the thia-zolidine ring makes dihedral angles of 13.51 (14), 48.6 (3) and 76.5 (3)° with the fluoro-phenyl ring and the major- and minor-disorder components of the phenyl ring, respectively. The central thia-zolidine ring adopts an envelope conformation. In the crystal, centrosymmetrically related cations and anions are linked into dimeric units via N-H⋯Br hydrogen bonds, which are further connected by weak C-H⋯Br hydrogen bonds into chains parallel to [110]. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (44.3%), Br⋯H/H⋯Br (16.8%), C⋯H/H⋯C (13.9%), F⋯H/H⋯F (10.3%) and S⋯H/H⋯S (3.8%) inter-actions.

| S-EPMC6505598 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 3-amino-5-phenyl-thia-zolidin-2-iminium bromide.

Project description:In the cation of the title salt, C9H12N3S+·Br-, the thia-zolidine ring adopts an envelope conformation with the C atom adjacent to the phenyl ring as the flap. In the crystal, N-H?Br hydrogen bonds link the components into a three-dimensional network. Weak ?-? stacking inter-actions between the phenyl rings of adjacent cations also contribute to the mol-ecular packing. A Hirshfeld surface analysis was conducted to qu-antify the contributions of the different inter-molecular inter-actions and contacts.

| S-EPMC6775745 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-5-phenyl-3-[(pyridin-4-yl-methyl-idene)amino]-thia-zolidin-2-iminium bromide monohydrate.

Project description:In the cation of the title salt, C15H15N4S+·Br-·H2O, the central thia-zolidine ring adopts an envelope conformation with puckering parameters Q(2) = 0.279 (4) Å and φ(2) = 222.5 (9)°. The mean plane of the thia-zolidine ring makes dihedral angles of 12.4 (2) and 66.8 (3)° with the pyridine and phenyl rings, respectively. The pyridine ring in the title mol-ecule is essentially planar (r.m.s deviation = 0.005 Å). In the crystal, the cations, anions and water mol-ecules are linked into a three-dimensional network, which forms cross layers parallel to the (120) and (20) planes via O-H⋯Br, N-H⋯Br and N-H⋯N hydrogen bonds. C-H⋯π inter-actions also help in the stabilization of the mol-ecular packing. Hirshfeld surface analysis and 2D (two-dimensional) fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (35.5%), C⋯H/H⋯C (23.9%), Br⋯H/H⋯Br (16.4%), N⋯H/H⋯N (10.6%) and S⋯H/H⋯S (7.9%) inter-actions.

| S-EPMC6127695 | biostudies-literature

5-Benzyl-idene-3-phenyl-2-phenyl-imino-1,3-thia-zolidin-4-one.

Project description:The title compound, C(22)H(16)N(2)OS, is a chalcone analog with a thia-zolidinone core that was synthesized as a potential cytotoxic and anti-cancer agent. The structure is commensurately modulated by unit-cell doubling along the direction of the a axis of the cell. The two crystallographically independent mol-ecules are differerentiated by the dihedral angle between the mean planes of the benzyl-idene phenyl group against the thia-zolidin-4-one moiety, which is 5.01 (7)° in one mol-ecule, and 17.41 (6)° in the other. The two mol-ecules are otherwise close to being indistinguishable and are related by crystallographic pseudo-translation. The two mol-ecules are not planar but are slightly bent with the benzyl-idene and phenyl-imino substituents being bent upwards with respect to the center planes of the two mol-ecules. The degree of bending of the two halves of the thia-zolidin-4-one moieties (defined as the planes that inter-sect at the S atom) are 11.08 (7) and 15.88 (7)°. Packing of the mol-ecules is facilitated by C-H⋯π inter-actions and slipped π-π stacking between one of the phenyl rings and a neighboring ethylene π system [distance between the centroid of the ethylene group and the closest phenyl C atom = 3.267 (2) Å, Cg(phenyl)⋯Cg(ethylene) = 3.926 Å].

| S-EPMC3152016 | biostudies-literature

3-[(5-Chloro-2-hy-droxy-benzyl-idene)amino]-2-sulfanyl-idene-1,3-thia-zolidin-4-one.

Project description:In the title compound, C10H7ClN2O2S2, the mean plane of the thioxo-thia-zolidine ring [maximum deviation = 0.032 (2) Å] is inclined to the benzene ring by 12.25 (4)°. There is a strong intra-molecular O-H⋯N hydrogen bond present. In the crystal, mol-ecules are linked via pairs of C-H⋯Cl hydrogen bonds, forming inversion dimers.

| S-EPMC3770396 | biostudies-literature

(5Z)-5-(2-Methyl-benzyl-idene)-3-phenyl-2-thioxo-1,3-thia-zolidin-4-one.

Project description:In the title compound, C(17)H(13)NOS(2), the heterocyclic ring is oriented at a dihedral angle of 74.43?(5)° with respect to the anilinic benzene ring and at a dihedral angle of 17.31?(9)° with respect to phenyl ring. An intra-molecular C-H?S inter-action occurs, resulting in an S(6) ring. In the crystal, the packing is consolidated by C-H?? inter-actions and possible very weak aromatic ?-? stacking [centroid-centroid separation = 4.025?(1)?Å].

| S-EPMC2971373 | biostudies-literature

(5Z)-5-(2-Hydroxy-benzyl-idene)-3-phenyl-2-thioxo-1,3-thia-zolidin-4-one.

Project description:In the title compound, C(16)H(11)NO(2)S(2), the dihedral angles between the heterocyclic ring and the phenyl and anilinic benzene rings are 9.68 (13) and 79.26 (6)°, respectively, and an intra-molecular C-H⋯S inter-action occurs. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds occur, leading to R(2) (2)(10) loops, and C-H⋯O and weak C-H⋯π inter-actions further consolidate the packing.

| S-EPMC2971093 | biostudies-literature

3-Benzyl-2-phenyl-1,3-thia-zolidin-4-one.

Project description:In the title compound, C(16)H(15)NOS, the thia-zolidine ring, which is essentially planar [maximum deviation = 0.071?(2)?Å], makes dihedral angles of 88.01?(8) and 87.21?(8)° with the terminal phenyl rings. The dihedral angle between the phenyl rings is 49.45?(5)°. In the crystal, mol-ecules are linked by a weak inter-molecular C-H?O hydrogen bond, forming a supra-molecular chain along the b axis. Furthermore, the crystal packing is stabilized by a weak C-H?? inter-action.

| S-EPMC3201390 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

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