Browse
Submit Data
Databases
API
Help

Dataset Information

13 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

4-Bromo-acetyl-3-phenyl-sydnone.

ABSTRACT:

In the title compound (systematic name

4-bromoacetyl-1,2,3-oxadiazol-3-ylium-5-olate), C(10)H(7)BrN(2)O(3), the 1,2,3-oxadiazole ring and bromo-acetyl group are essentially planar [maximum deviation = 0.010 (4) and 0.013 (3) Å respectively] and form dihedral angles of 59.31 (19) and 67.96 (11)°, respectively, with the phenyl ring. The 1,2,3-oxadiazole ring is twisted slightly from the mean plane of the bromo-acetyl group, forming a dihedral angle of 9.16 (24)°. In the crystal, mol-ecules are linked by pairs of weak C-H⋯O hydrogen bonds into inversion dimers with R(2) (2)(12) ring motifs. The dimers are further connected by weak C-H⋯O hydrogen bonds into an infinite tape parallel to the b axis. In addition, π-π stacking inter-actions [centroid-centroid distance = 3.6569 (19) Å] and short inter-molecular contacts [O⋯O = 2.827 (3) and C⋯C = 3.088 (5) Å] are observed.

SUBMITTER: Fun HK

PROVIDER: S-EPMC3393916 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Crystal structure of 4-(2-bromo-prop-ion-yl)-3-phenyl-sydnone.

Project description:Sydnones are a class of mesoionic compounds containing a five-membered heterocyclic ring. In general, sydnone com-pounds are synthesized with an aromatic substutuent at the N(3) position. This feature, adds to the stability of the heterocyclic ring. In the title compound {systematic name: 4-(2-bromo-propano-yl)-3-phenyl-1,2,3?(5)-oxa-diazol-3-ylium-5-olate}, C11H9BrN2O3, the aromatic substitutent is an unsubstituted phenyl ring. The sydnone ring is almost planar, with a maximum deviation from the mean plane of 0.023?(1)?Å, but is not coplanar with the phenyl ring, having a dihedral angle of 40.93?(8)°. The carbonyl side chain is twisted relative to the syndone ring by 15.8?(2)°. The mol-ecules are packed in the unit cell as pairs related by an inversion center at (1, 0, 1/2). The pairs inter-act via ?-stacking, with the distance separating the centroids being 3.824?(1)?Å. The Br atom has two contacts, one to an N atom in a neighboring asymmetric unit with a distance of 3.346?(2)?Å (the sum of the van der Waals radii is 3.40?Å) and a second to an H atom with a distance of 3.03?Å. The contact with the H atom is perpendicular (C-Br?H = 98.60°) to the C-Br bond, and that to the N atom is linear [C-Br?N = 169.10?(5)°] to the C-Br bond. The O atom of the sydnone ring is involved in two hydrogen bonds, one intra-molecular with a donor-acceptor distance of 3.1486?(19)?Å and a second that is inter-molecular, with a phenyl H atom as the donor and has a donor-acceptor distance of 3.346?(2)?Å.

| S-EPMC4257336 | biostudies-literature

4-Acetyl-3-(p-anis-yl)sydnone.

Project description:THE ASYMMETRIC UNIT OF THE TITLE COMPOUND [SYSTEMATIC NAME: 4-acetyl-3-(4-meth-oxy-phen-yl)-1,2,3-oxadiazol-3-ium-5-olate], C(11)H(10)N(2)O(4), contains four crystallographically independent mol-ecules. The 1,2,3-oxadiazole rings are almost planar [maximum deviations = 0.006?(3), 0.006?(3), 0.002?(3) and 0.009?(3)?Å] and form dihedral angles of 55.03?(14), 61.02?(13), 58.36?(14) and 53.79?(15)° with their attached benzene rings. In the crystal, inter-molecular C-H?O and C-H?N hydrogen bonds link the mol-ecules, forming sheets parallel to (011).

| S-EPMC3120361 | biostudies-literature

4-({[6-(4-Chloro-benz-yl)-4-methyl-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfan-yl}acetyl)-3-phenyl-sydnone.

Project description:In the title syndone (1,2,3-oxadiazol-3-ylium-5-olate) compound, C(21)H(16)ClN(5)O(4)S, the dihedral angle between the benzene and oxadiazole rings is 55.62?(11)° and that between the triazine and the chloro-substituted phenyl rings is 82.45?(9)°. There is an intra-molecular C-H?S hydrogen bond, which generates an S(5) ring motif. In the crystal, inversion dimers linked by pairs of C-H?O hydrogen bonds generate R(2) (2)(20) loops. The dimers are connected by C-H?N and C-H?O hydrogen bonds.

| S-EPMC3099780 | biostudies-literature

4-Acetyl-3-[2-(eth-oxy-carbon-yl)phen-yl]sydnone.

Project description:Sydnones, which contain a mesoionic five-membered heterocyclic ring, are more stable if synthesized with an aromatic substutuent at the N3 position. In the title compound {sys-tematic name: 4-acetyl-3-[2-(eth-oxy-carbon-yl)phen-yl]-1,2,3-oxa-diazol-3-ylium-5-olate}, C13H12N2O5, the aromatic substitutent is 2-(eth-oxy-carbon-yl)phenyl. Intra- and inter-molecular hydrogen bonds are observed. The inter-planar angle between the sydnone and benzene rings is 71.94?(8)°. ?-ring?carbon-yl inter-actions of 3.2038?(16)?Å arise between the sydnone ring and a symmetry-related C=O group.

| S-EPMC3884322 | biostudies-literature

4-Bromo-phenyl benzoate.

Project description:The structure of the title compound (4BPBA), C(13)H(9)BrO(2), is similar to that of phenyl benzoate (PBA), 4-methyl-phenyl benzoate (4MePBA) and 4-methoxy-phenyl benzoate, with somewhat different bond parameters. The dihedral angle between the phenyl and benzoyl rings in 4BPBA is 58.43 (17)°, compared with values of 55.7° in PBA and 60.17 (7)° in 4MPBA. The mol-ecules in the title compound are packed into infinite chains in the a-axis direction.

| S-EPMC2960956 | biostudies-literature

4-Bromo-N-phenyl-benzamide.

Project description:The mol-ecule of the title benzamide derivative, C(13)H(10)BrNO, is twisted with the dihedral angle between the phenyl and 4-bromo-phenyl rings being 58.63?(9)°. The central N-C=O plane makes dihedral angles of 30.2?(2) and 29.2?(2)° with the phenyl and 4-bromo-phenyl rings, respectively. In the crystal, mol-ecules are linked by N-H?O hydrogen bonds into chains along [100]. C-H?? contacts combine with the N-H?O hydrogen bonds, to form a three-dimensional network.

| S-EPMC3344194 | biostudies-literature

4-Bromo-N-phenyl-benzamidoxime.

Project description:The title compound, C(13)H(11)BrN(2)O, a hydroxy-amidine derivative (an amidoxime), was obtained by addition of the corresponding imidoyl chloride to hydroxy-lamine. The benzene and phenyl rings are twisted from the mean plane of the hydroxy-amidine group by 34.4?(1) and 59.2?(1)°, respectively. In the crystal structure, inter-molecular O-H?N hydrogen bonds link pairs of mol-ecules, forming centrosymmetric dimers.

| S-EPMC2971251 | biostudies-literature

4-Bromo-N-phenyl-aniline.

Project description:In the title compound, C(12)H(10)BrN, the dihedral angle between the benzene rings is 52.5 (1)°, whereas the pitch angles, or the angles between the mean plane of each aryl group 'propeller blade' and the plane defined by the aryl bridging C-N-C angle, are 19.6 (2) and 36.2 (3)°. While the N-H group is not involved in hydrogen-bonding inter-actions, the structure exhibits a network of inter-molecular C-H⋯π and N-H⋯π inter-actions.

| S-EPMC3099920 | biostudies-literature

2-Bromo-1-phenyl-ethanone.

Project description:The title compound, C(8)H(7)BrO, is a halogenated derivative of acetophenone. The mol-ecule shows noncrystallographic C(s) symmetry. The intra-cyclic C-C-C angles cover the range 118.8 (2)-120.4 (3)°. In the crystal structure, C-H⋯O contacts connect the mol-ecules into undulating sheets perpendicular to the crystallographic c axis.

| S-EPMC3089288 | biostudies-literature

5-Bromo-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

Project description:In the title compound, C(20)H(13)BrO(2)S, the O atom and the phenyl group of the phenyl-sulfinyl substituent are located on opposite sides of the plane of the benzofuran system. The S-bound phenyl ring is almost perpendicular to this plane [80.35?(8)°]. The phenyl ring in the 2-position is twisted with respect to the benzofuran plane, making a dihedral angle of 16.0?(1)°.

| S-EPMC2971280 | 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