Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Thieno[3,4-d][1,3]dithiole-2-thione.

ABSTRACT: In the title compound, C(5)H(2)S(4), the terminal monocyclic S atom deviates by 0.117?(1)?Å from the mean plane of the other non-H atoms (r.m.s. deviation = 0.001?Å). All six C-S bonds and the central C-C bond in the rings are characterized by ?-conjugated lengths, endowing the mol-ecule with high ?-conjugation. In the crystal, the mol-ecules are parallel packed, forming columnar stacks along the a axis. Short inter-molecular S?S contacts [3.397?(1) and 3.486?(1)?Å], are observed.

SUBMITTER: Wen HW

PROVIDER: S-EPMC3247483 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Thieno[3,4-d][1,3]dithiole-2-thione.

Wen Hua-Wen HW Fang Qi Q

Acta crystallographica. Section E, Structure reports online 20111029 Pt 11

In the title compound, C(5)H(2)S(4), the terminal monocyclic S atom deviates by 0.117 (1) Å from the mean plane of the other non-H atoms (r.m.s. deviation = 0.001 Å). All six C-S bonds and the central C-C bond in the rings are characterized by π-conjugated lengths, endowing the mol-ecule with high π-conjugation. In the crystal, the mol-ecules are parallel packed, forming columnar stacks along the a axis. Short inter-molecular S⋯S contacts [3.397 (1) and 3.486 (1) Å], are observed. ...[more]

PMID: 22220101

Similar Datasets

5-Isopropyl-idene-1,3-dithiolo[4,5-d][1,3]dithiole-2-thione.

Project description:The title compound, C(7)H(6)S(5), contains a 5-yl-idene-1,3-dithiolo[4,5-d][1,3]dithiole-2-thione framework, which is an important synthetic precursor of multi-dimensional organic superconductors and conductors. The mol-ecular framework is planar with an r.m.s. deviation of 0.012 Å for the non-H atoms. In the crystal structure, mol-ecules are linked by short inter-molecular S⋯S inter-actions [3.501 (5) and 3.581 (4) Å], constructing a zigzag mol-ecular tape network along the c axis.

| S-EPMC2977732 | biostudies-literature

4-Bromo-5-[(2-bromo-ethyl)-sulfanyl]-1,3-dithiole-2-thione.

Project description:The title compound, C(5)H(4)Br(2)S(4), consists of a statistically planar, 4-bromo-1,3-dithiole-2-thione unit [maximum deviation from the ring plane 0.001?(2)?Å], with a bromo-ethyl-sulfanyl substituent in the 5-position. In the crystal structure, weak inter-molecular S?S [3.438?(15) and 3.522?(15)?Å] and S?Br [3.422?(14) and 3.498?(14)?Å] inter-actions generate a three-dimensional supra-molecular architecture.

| S-EPMC2970213 | biostudies-literature

6,7,8,9,10,11,12,13-Octa-hydro-5H-1,3-dithiole[4,5-b][1,4]dithia-cyclo-tridecine-2-thione.

Project description:In the crystal structure of the title compound, C(12)H(18)S(5), no significant inter-molecular π-π inter-actions are found. Weak inter-molecular C-S⋯π [S⋯centroid = 3.787 (1) Å] inter-actions and van der Waals forces may be effective in the stabilization of the structure.

| S-EPMC2960369 | biostudies-literature

5-(4,5-Diiodo-1,3-dithiol-2-yl-idene)-4',5'-bis-(methyl-sulfan-yl)-2,2'-bi-1,3-dithiole-4(5H)-thione.

Project description:The mol-ecular skeleton of the title mol-ecule, C(11)H(6)I(2)S(9), is nearly planar [maximum deviation 0.052 (3) Å] except for the two methyl groups. In the crystal, mol-ecules related by translation along b axis are associated into columns through π-π inter-actions between the five-membered rings, with a centroid-centroid distance of 3.593 (5) Å. Inter-action between adjacent columns is accomplished by short S⋯I contacts of 3.2099 (4) Å.

| S-EPMC2970979 | biostudies-literature

3-[1-(3,4-Dichloro-phen-yl)eth-yl]-1,3-thia-zinane-2-thione.

Project description:In the title compound, C(12)H(13)Cl(2)NS(2), the thia-zinane ring adopts a half-boat conformation. An intra-molecular C-H?S hydrogen bond is observed. In the crystal structure, centrosymmetrically related mol-ecules inter-act through an aromatic ?-? stacking inter-actions, with a centroid-centroid separation of 3.790?(2)?Å.

| S-EPMC2971749 | biostudies-literature

4'-Phenyl-3,4-di-hydro-2H-spiro-[naph-tha-lene-1,3'-[1,2,4]triazole]-5'-thione.

Project description:In the title mol-ecule, C17H15N3S, the phenyl group makes a dihedral angle of 57.29?(11)° with the mean plane of the triazole ring, which in turn makes an angle of 86.83?(12)° with the plane of the aromatic portion of the tetra-hydro-naphthalene moiety. In the crystal, mol-ecules are linked by weak C-H?S hydrogen bonds into supra-molecular chains propagating along the a-axis direction. Weak C-H?? inter-actions are also observed.

| S-EPMC4051013 | biostudies-literature

1-(3,4-Dichloro-benz-yl)pyridinium bis-(2-sulfanyl-idene-1,3-dithiole-4,5-dithiol-ato-κS,S')nickelate(III).

Project description:The title compound, (C(12)H(10)Cl(2)N)[Ni(C(3)S(5))(2)], is an ion-pair complex consisting of 1-(3,4-dichloro-benz-yl)pyridinium cations and [Ni(dmit)(2)] anions (dmit = 2-sulfanyl-idene-1,3-dithiole-4,5-dithiol-ate). In the anion, the Ni(III) ion exhibits a square-planar coordination involving four S atoms from two dmit ligands. In the crystal, weak S⋯S [3.368 (2) and 3.482 (3) Å], Ni⋯S [3.680 (2) Å] and Cl⋯S [3.491 (2) Å] inter-actions and C-H⋯S hydrogen bonds lead to a three-dimensional supra-molecular network.

| S-EPMC3246987 | biostudies-literature

1,3-Dibenzyl-imidazolidine-2-thione.

Project description:In the title compound, C(17)H(18)N(2)S, the imidazolidine ring adopts a twisted conformation. In the crystal, mol-ecules are linked by slipped π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-to-centroid distance = 3.903 (2) Å].

| S-EPMC3414971 | biostudies-literature

Thieno[3,4-<i>d</i>]pyrimidin-4(3<i>H</i>)-thione: an effective, oxygenation independent, heavy-atom-free photosensitizer for cancer cells.

Project description:All-organic, heavy-atom-free photosensitizers based on thionation of nucleobases are receiving increased attention because they are easy to make, noncytotoxic, work both in the presence and absence of molecular oxygen, and can be readily incorporated into DNA and RNA. In this contribution, the DNA and RNA fluorescent probe, thieno[3,4-d]pyrimidin-4(1H)-one, has been thionated to develop thieno[3,4-d]pyrimidin-4(3H)-thione, which is nonfluorescent and absorbs near-visible radiation with about 60% higher efficiency. Steady-state absorption and emission spectra are combined with transient absorption spectroscopy and CASPT2 calculations to delineate the electronic relaxation mechanisms of both pyrimidine derivatives in aqueous and acetonitrile solutions. It is demonstrated that thieno[3,4-d]pyrimidin-4(3H)-thione efficiently populates the long-lived and reactive triplet state generating singlet oxygen with a quantum yield of about 80% independent of solvent. It is further shown that thieno[3,4-d]pyrimidin-4(3H)-thione exhibits high photodynamic efficacy against monolayer melanoma cells and cervical cancer cells both under normoxic and hypoxic conditions. Our combined spectroscopic, computational, and in vitro data demonstrate the excellent potential of thieno[3,4-d]pyrimidin-4(1H)-thione as a heavy-atom-free PDT agent and paves the way for further development of photosensitizers based on the thionation of thieno[3,4-d]pyrimidine derivatives. Collectively, the experimental and computational results demonstrate that thieno[3,4-d]pyrimidine-4(3H)-thione stands out as the most promising thiobase photosensitizer developed to this date.

| S-EPMC10445467 | biostudies-literature

5,6-Diamino-1,3-benzodithiole-2-thione.

Project description:The mol-ecule of the title compound, C(7)H(6)N(2)S(3), is almost planar, the dihedral angle between the benzene plane and the 1,3-dithiole-2-thione plane being 2.21?(6)°. In the crystal, mol-ecules are linked by inter-molecular N-H?S and N-H?N hydrogen bonds into a three-dimensional network. The crystal packing also exhibits weak inter-molecular S?S inter-actions [3.5681?(9)?Å].

| S-EPMC3011669 | 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