Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure of diethyl (E)-2-[(benzo-furan-2-yl)methyl-idene]succinate.

ABSTRACT: The title compound, C17H18O5, was synthesized by a base-free catalytic Wittig reaction. The mol-ecule consists of a diethyl itaconate unit, which is connected via the C=C double bond to a benzo-furan moiety. The benzo-furan ring system (r.m.s. deviation = 0.007 Å) forms dihedral angles of 79.58 (4) and 12.12 (10)° with the mean planes through the cis and trans eth-oxy-carbonyl groups, respectively. An intra-molecular C-H⋯O hydrogen bond involving the O atom of the benzo-furan moiety is observed. In the crystal, mol-ecules are linked into ribbons running parallel to the b axis by C-H⋯O hydrogen bonds.

SUBMITTER: Schirmer ML

PROVIDER: S-EPMC4645082 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure of diethyl (E)-2-[(benzo-furan-2-yl)methyl-idene]succinate.

Schirmer Marie-Luis ML Spannenberg Anke A Werner Thomas T

Acta crystallographica. Section E, Crystallographic communications 20151024 Pt 11

The title compound, C17H18O5, was synthesized by a base-free catalytic Wittig reaction. The mol-ecule consists of a diethyl itaconate unit, which is connected via the C=C double bond to a benzo-furan moiety. The benzo-furan ring system (r.m.s. deviation = 0.007 Å) forms dihedral angles of 79.58 (4) and 12.12 (10)° with the mean planes through the cis and trans eth-oxy-carbonyl groups, respectively. An intra-molecular C-H⋯O hydrogen bond involving the O atom of the benzo-furan moiety is observed. ...[more]

PMID: 26594572

Similar Datasets

Crystal structure of (E)-diethyl 2-[(1-phenyl-sulfonyl-1H-indol-3-yl)methyl-idene]succinate.

Project description:In the title compound, C23H23NO6S, the phenyl ring is perpendicular [dihedral angle = 89.34 (9)°] to the indole ring system. In the mol-ecule, the eth-oxy groups are each disordered over two sets of sites with occupancy ratios of 0.671 (6):0.329 (6) and 0.75 (3):0.25 (3). The mol-ecular conformation is consolidated by a weak C-H⋯O interaction, which generates an S(6) graph-set motif. The packing of the mol-ecules in the crystal structure features weak C-H⋯π inter-actions.

| S-EPMC4719962 | biostudies-literature

Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-di-hydro-benzo-furan-1-yl-idene)malonate.

Project description:The reaction of diethyl malonate with phthaloyl chloride in aceto-nitrile in the presence of tri-ethyl-amine and magnesium chloride results in the formation of the title compound, diethyl 2-(3-oxo-1,3-di-hydro-2-benzo-furan-1-yl-idene)propane-dioate, C15H14O6. One of the ester groups of the diethyl malonate fragment is almost coplanar with the isobenzo-furan unit, while the plane of the other group is perpendicular to it [dihedral angles = 5.45 (3) and 83.30 (3)°, respectively]. The C-C and C-O distances both in the heterocyclic furan ring and the diethyl malonate fragment are indicative of the dipolar delocalization occurring within the isobenzo-furan unit. This delocalization is likely to be responsible for the unusual inter-molecular O⋯O contact [2.756 (2) Å], established between the O atom of the furan ring and the carbonyl O atom of the diethyl malonate fragment. In the crystal, weak C-H⋯O inter-actions are observed, which link the mol-ecules into [100] chains.

| S-EPMC5730322 | biostudies-literature

Crystal structure of diethyl 2-[(2-sulfan-yl-quinolin-3-yl)methyl-idene]malonate.

Project description:In the title compound, C17H17N O4S, the quinoline ring system is nearly planar, with a maximum deviation of 0.0496 (16) Å. A weak intra-molecular C-H⋯O inter-action is observed. In the crystal, C-H⋯O, S-H⋯N and π-π stacking inter-actions between the fused benzene ring of quinoline and the pyridine moieties [shortest centroid-centroid distance = 3.6754 (11) Å] are observed. Inversion-related weak C-H⋯O inter-molecular inter-actions diagonally along [010], with R 2 (2)(10) ring motifs, and S-H⋯N inter-molecular inter-actions diagonally along [100], with R 2 (2)(8) ring motifs, are present, forming a three-dimensional network structure. No classical hydrogen bonds are observed.

| S-EPMC4571415 | biostudies-literature

Crystal structure of 5-iodo-2-methyl-3-[(4-methyl-phenyl)-sulfon-yl]-1-benzo-furan.

Project description:In the title compound, C16H13IO3S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.015 (2) Å] and the 4-methyl-phenyl ring is 70.35 (5)°. In the crystal, mol-ecules are linked by pairs of π-π inter-actions between the furan and benzene rings, with centroid-centroid distances of 3.667 (3) and 3.701 (3) Å. The mol-ecules stack along the a-axis direction. In addition, pairs of C-H⋯O hydrogen bonds between inversion-related dimers [which generate R 2 (2)(10) loops] and a short I⋯I [3.7534 (3) Å] contact are observed.

| S-EPMC4186123 | biostudies-literature

Crystal structure of 2,5-dimethyl-3-(2-methyl-phenyl-sulfon-yl)-1-benzo-furan.

Project description:The title compound, C17H16O3S, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The dihedral angle between the benzo-furan ring system [r.m.s. deviation of 0.013 (1) for A and 0.009 (1) Å for B] and the 2-methyl-phenyl ring is 83.88 (5) for A and 86.94 (5)° for B. In the crystal, the B mol-ecules are linked into a chain along the b-axis direction by C-H⋯O hydrogen bonds. The A mol-ecules are connected on either side of this chain by further C-H⋯O hydrogen bonds. These chains are linked via C-H⋯π inter-actions, forming sheets parallel to (100). There are also very weak π-π inter-actions present [centroid-centroid distance = 3.925 (11) Å] involvingthe 2-methyl-phenyl rings of neighbouring A and B mol-ecules.

| S-EPMC4257330 | biostudies-literature

Crystal structure of 2,5-dimethyl-3-(3-methyl-phenyl-sulfon-yl)-1-benzo-furan.

Project description:In the title compound, C17H16O3S, the dihedral angle between the plane of the benzo-furan ring system [r.m.s. deviation = 0.010 (1) Å] and that of the 3-methyl-phenyl ring is 79.09 (5)°. Intra-molecular C-H⋯O hydrogen bonds are observed. In the crystal, mol-ecules are connected into a chain along the c-axis direction by two different pairs of inversion-generated inter-actions: C-H⋯π hydrogen bonds between the methyl groups and the benzene rings of the 3-methyl-phenyl fragments and π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.673 (2) Å].

| S-EPMC4186096 | biostudies-literature

Crystal structure of 2,5-dimethyl-3-(2-methyl-phenyl-sulfin-yl)-1-benzo-furan.

Project description:In the title compound, C17H16O2S, the dihedral angle between the benzo-furan ring system [r.m.s. deviation = 0.009 (1) Å] and the 2-methyl-phenyl ring is 86.72 (4)°. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into columns along the b-axis direction.

| S-EPMC4571393 | biostudies-literature

Crystal structure of 5-bromo-2,4,6-trimethyl-3-[(2-methyl-phen-yl)sulfin-yl]-1-benzo-furan.

Project description:In the title compound, C18H17BrO2S, the dihedral angle between the mean planes of the benzo-furan [r.m.s. deviation = 0.025 (2) Å] and the 2-methyl-benzene rings is 87.87 (5)°. In the crystal, mol-ecules are linked into supra-molecular layers parallel to (0-11) by C-H⋯O hydrogen bonds and Br⋯Br [3.4521 (5) Å] contacts. These are connected into a three-dimensional architecture via C-H⋯π inter-actions, which link inversion-related mol-ecules into dimers, and π-π inter-actions between the benzene and furan rings [centroid-centroid distance = 3.573 (2) Å].

| S-EPMC4571419 | biostudies-literature

Crystal structure of 2-(3-fluoro-phen-yl)-5-iodo-3-methyl-sulfinyl-1-benzo-furan.

Project description:In the title compound, C15H10FIO2S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.015 (2) Å] and the 3-fluoro-phenyl ring is 29.63 (7)°. In the crystal, mol-ecules are linked into inversion dimers along the b-axis direction by two different pairs of C-H⋯O hydrogen bonds and I⋯O [3.228 (1) Å] contacts.

| S-EPMC4257291 | biostudies-literature

Crystal structure of 5-fluoro-2-(3-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzo-furan.

Project description:In the title compound, C15H10F2O2S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.015 (1) Å] and the 3-fluoro-phenyl ring is 26.60 (5)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯F hydrogen bonds, and by π-π inter-actions between the benzo-furan rings of inversion-related mol-ecules [centroid(benzene)-centroid(furan) distance = 3.819 (2) Å], forming a three-dimensional network.

| S-EPMC4257342 | 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