Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structures of (1E,4E)-1,5-bis-(5-bromo-thio-phen-2-yl)-2,4-di-methyl-penta-1,4-dien-3-one and (E)-4-(5-bromo-thio-phen-2-yl)-1,3-di-phenyl-but-3-en-2-one.

ABSTRACT: The title compounds, C15H12Br2OS2, (I), and C20H15BrOS, (II), were synthesized by employing Claisen-Schmidt condensation of pentan-3-one and di-benzyl-acetone with 5-bromo-thio-phene-2-carbaldehyde in the presence of methano-lic KOH. Even though 1:2 products were expected in both of the reactions, 1:2 and 1:1 products were obtained as (I) and (II), respectively. In (I), the two methyl groups are trans to each other, 29.5 (7) and 28.7 (7)° away from the central carbonyl bond between them, whereas the two phenyl rings of di-benzyl-acetone subtend a dihedral angle of 53.09 (18)°. In the crystal of (I), C-H⋯O hydrogen bonds define mol-ecular chains along c. A second type of mol-ecular chain is formed along b by means of C-Br⋯π inter-actions. These two families of mol-ecular chains are stacked by π-π inter-actions, forming a three-dimensional supra-molecular architecture. In (II), similar C-H⋯O hydrogen bonds as in (I) define inversion dimers, whilst C-H⋯.π inter-actions build a staircase structure along the a axis.

SUBMITTER: Nithya C

PROVIDER: S-EPMC4770966 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

(1E,4E)-1,5-Bis(thio-phen-3-yl)penta-1,4-dien-3-one.

Project description:The title compound, C(13)H(10)OS(2), exhibits twists between the central C(3)O and ethene residues [O-C-C-C torsion angles = -8.4?(3) and 11.8?(3)°], and between the ethene and adjacent thio-phenyl residues [C-C-C-C torsion angles = -4.2?(3) and 10.5?(3)°]. As a result, the mol-ecule is non-planar, the dihedral angle formed between the terminal thio-phenyl groups being 15.45?(10)°. The presence of C-H?O inter-actions involving the bifurcated carbonyl O atom leads to supra-molecular arrays in the ac plane. These are linked into a three-dimensional architecture by C-H?? inter-actions involving both thio-phenyl residues.

| S-EPMC3200598 | biostudies-literature

(1E,4E)-1,5-Bis[4-(di-ethyl-amino)-phen-yl]penta-1,4-dien-3-one.

Project description:There are two crystallograpically independent mol-ecules in the asymmetric unit of the title bis-chalcone derivative, C25H32N2O. Both mol-ecules are twisted with a dihedral angle between the two substituted benzene rings of 11.19?(16)° in one mol-ecule and 14.40?(15)° in the other. The central penta-1,4-dien-3-one fragments make dihedral angles of 8.49?(17) and 4.26?(17)° with the two adjacent benzene rings in one mol-ecule, whereas the corresponding values are 8.42?(16) and 6.18?(16)° in the other. In the crystal, mol-ecules are arranged into chains along the c-axis direction. Adjacent chains are inter-linked by weak inter-molecular C-H?O inter-actions. The crystal is further stabilized by C-H?? inter-actions.

| S-EPMC4011286 | biostudies-literature

(1E,4E)-1,5-Bis(4-methyl-phen-yl)penta-1,4-dien-3-one.

Project description:The title compound, C(19)H(18)O, crystallizes in a non-centrosymmetric space group although the mol-ecule has no chiral centre. The dihedral angle between the aromatic rings is 20.43?(13)°. The structure is stabilized by two intra-molecular hydrogen bonds, and by four ?-? and three C-H?? inter-actions between the aromatic rings. The perpendicular distances between the centroids of the rings involved in the ?-? inter-actions have values of 1.996, 2.061, 2.181 and 2.189?Å.

| S-EPMC2962047 | biostudies-literature

(1E,4E)-1,5-Bis(2,4,5-trimethoxy-phen-yl)penta-1,4-dien-3-one.

Project description:There are three mol-ecules in the asymmetric unit of the title compound, C(23)H(26)O(7), in which the dihedral angles between two benzene rings are 4.34?(9), 18.11?(8) and 8.54?(8)°. The central penta-1,4-dien-3-one fragment makes dihedral angles of 3.95?(9) and 3.32?(16)° with the two adjacent benzene rings in one mol-ecule, whereas the corresponding pairs of angles in the other two mol-ecules are 10.34?(9)/17.46?(8)° and 7.87?(8)/13.33?(8)°. In the crystal, mol-ecules are linked by inter-molecular C-H?O and C-H?? weak inter-actions into a three-dimensional network. Finally, ?-? inter-actions [centroid?centroid distances = 3.5984?(10) and 3.5545?(10)?Å] are observed.

| S-EPMC2979664 | biostudies-literature

(1E,4E)-1,5-Bis[2-(trifluoro-meth-yl)phen-yl]penta-1,4-dien-3-one.

Project description:In the title compound, C(19)H(12)F(6)O, a monoketone derivative of curcumin, both double bonds have a trans conformation. The mol-ecule is mostly planar with all C and O atoms essentially coplanar, with the exception of one benzene ring, which is tilted by 17.18?(1)° with respect to the plane of the remainder of the mol-ecule. The r.m.s. deviation from planarity of the coplanar section is 0.0097?Å. The crystal packing features weak C-H?O and C-H?F inter-actions.

| S-EPMC3569239 | biostudies-literature

(1E,4E)-1,5-Bis(2,4,6-trimeth-oxy-phen-yl)penta-1,4-dien-3-one.

Project description:There are two crystallographically independent mol-ecules in the asymmetric unit of the title bis-chalcone derivative, C(23)H(26)O(7). The mol-ecules are unsymmetrical and almost planar: the dihedral angle between two benzene rings is 1.04?(7)° in one mol-ecule and 2.31?(7)° in the other. The central penta-1,4-dien-3-one fragment makes dihedral angles of 7.61?(7) and 6.82?(7)° with the two adjacent benzene rings in one mol-ecule, while the corresponding values are 7.85?(7) and 9.42?(6)° in the other. In both mol-ecules, the three meth-oxy groups of the two 2,4,6-trimeth-oxy-phenyl units are coplanar with the attached benzene rings [C-O-C-C- torsion angles of -1.5?(2), -7.2?(2) and 4.1?(2)° in one mol-ecule and -0.7?(2), -5.5?(2) and -0.6?(2)° in the other]. The mol-ecular conformations are stabilized by weak intra-molecular C-H?O inter-actions generating two S(6) ring motifs. In the crystal, mol-ecules are linked by weak inter-molecular C-H?O inter-actions into zigzag chains parallel to the c axis. The crystal structure is further stabilized by C-H?? inter-actions and ?-? inter-actions with centroid-centroid distances of 3.6433?(8)?Å.

| S-EPMC3050352 | biostudies-literature

(1E,4E)-1-(3-Nitro-phen-yl)-5-phenyl-penta-1,4-dien-3-one.

Project description:In the title compound, C(17)H(13)NO(3), the dihedral angle between the benzene rings is 31.21?(5)°. In the crystal, inversion dimers linked by pairs of C-H?O hydrogen bonds occur. A C-H?? inter-action is also indicated.

| S-EPMC3254429 | biostudies-literature

(1E,4E)-1-(Thio-phen-2-yl)-5-(2,6,6-trimethyl-cyclo-hex-1-en-1-yl)penta-1,4-dien-3-one.

Project description:In the title curcumin-ionone derivative, C(18)H(22)OS, the dihedral angle between the thia-zole ring and the mean plane through the cyclo-hexene ring is 5.16?(10)°. The mol-ecule has an E conformation for each of the olefinic bonds.

| S-EPMC3379426 | biostudies-literature

(1E,4E)-1,5-Bis(2,4-dimethyl-phen-yl)penta-1,4-dien-3-one.

Project description:In the title compound, C(21)H(22)O, a derivative of the biologically active compound curcumin, the dihedral angle between the aromatic ring planes is 20.57?(11)°.

| S-EPMC2969860 | biostudies-other

(1E,4E)-1,5-Bis(2,6-difluoro-phen-yl)penta-1,4-dien-3-one.

Project description:The mol-ecule of the title compound, C(17)H(10)F(4)O, is roughly planar, with a dihedral angle of 5.59?(14)° between the two phenyl rings. The mol-ecule has an E conformation with respect to the olefinic bonds. In the crystal, mol-ecules are connected through C-H?O hydrogen bonds and there is slipped ?-? stacking [centroid-centroid distance = 3.7983?(18), slippage =1.309?;Å] between symmetry-related benzene rings.

| S-EPMC3099841 | biostudies-other

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