Browse
Submit Data
Databases
API
Help

Dataset Information

14 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure of a photobiologically active brominated angular pyran-ocoumarin: bromo-hy-droxy-seselin.

ABSTRACT: The title compound, C₁₄H₁₃BrO₃ [systematic name: rac-(9S,10R)-9-bromo-10-hy-droxy-8,8-dimethyl-9,10-di-hydro-2H,8H-pyrano[2,3-f]chromen-2-one], is a substituted pyran-ocoumarin, obtained by bromination of seselin [8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one], which was isolated from the Indian herb Trachyspermum stictocarpum (Aajmod). The pyrano ring has a distorted half-chair conformation and its mean plane is inclined to the coumarin mean plane by 1.6?(2)°. In the crystal, mol-ecules are linked by pairs of O-H?O hydrogen bonds, forming inversion dimers with an R²₂(16) ring motif. The dimers stack along the a-axis direction and are linked by offset ?-? inter-actions, forming columns [inter-centroid distance = 3.514?(4)?Å].

SUBMITTER: Bauri AK

PROVIDER: S-EPMC5347075 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure of a photobiologically active brominated angular pyran-ocoumarin: bromo-hy-droxy-seselin.

Bauri A K AK Foro Sabine S Rahman A F M Mustafizur AF

Acta crystallographica. Section E, Crystallographic communications 20170228 Pt 3

The title compound, C14H13BrO3 [systematic name: rac-(9S,10R)-9-bromo-10-hy-droxy-8,8-dimethyl-9,10-di-hydro-2H,8H-pyrano[2,3-f]chromen-2-one], is a substituted pyran-ocoumarin, obtained by bromination of seselin [8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one], which was isolated from the Indian herb Trachyspermum stictocarpum (Aajmod). The pyrano ring has a distorted half-chair conformation an ...[more]

PMID: 28316830

Similar Datasets

Crystal structure of 3-bromo-2-hy-droxy-benzoic acid.

Project description:Mutual carbox-yl-carboxyl O-H?O hydrogen bonds link the mol-ecules of the title compound, C7H5BrO3, into centrosymmetric dimers which display a central R 2 (2)(8) ring motif. In addition, there is an intra-molecular hydrox-yl-carboxyl O-H?O inter-action present. A comparison with the crystal structures of 59 other substituted derivatives of salicylic acid shows that both the centrosymmetric carbox-yl-carboxyl O-H?O dimer and the stacking mode of mol-ecules along the short a axis observed in the title structure are frequent packing motifs in this set.

| S-EPMC4420063 | biostudies-literature

Crystal structure of 3-bromo-2-hy-droxy-benzo-nitrile.

Project description:The crystal structure of the title compound, C7H4BrNO, has been determined, revealing a partial mol-ecular packing disorder such that a 180° rotation of the mol-ecule about the phenol C-O bond results in disorder of the bromine and nitrile groups. The disorder has been parameterized as a disorder of only the bromine and nitrile substituents on a unique phenol ring. An intra-molecular O-H⋯Br contact occurs. In the crystal, O-H⋯Br/O-H⋯Nnitrile hydrogen bonding is present between the disordered bromine and nitrile substituents and the phenol group, forming a spiral chain about a twofold screw axis extending parallel to the b-axis direction. Within this spiral chain, the mol-ecules also inter-act, forming offset face-to-face π-stacking inter-actions with plane-to-centroid distance of 3.487 (1) Å.

| S-EPMC4518954 | biostudies-literature

Crystal structure of (E)-4-hy-droxy-3-{1-[(4-hy-droxy-phen-yl)imino]-eth-yl}-6-methyl-2H-pyran-2-one.

Project description:In the title Schiff base, C14H13NO4, which adopts the phenol-imine tautomeric form, the dihedral angle between the planes of the benzene and heterocyclic (r.m.s. deviation = 0.037 Å) rings is 53.31 (11)°. An intra-molecular O-H⋯N hydrogen bond closes an S(6) ring. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds to generate C(11) chains propagating in the [010] direction. A weak C-H⋯O link is also observed, leading to the formation of R (5) 5(32) rings extending parallel to the (101) plane.

| S-EPMC4571398 | biostudies-literature

Crystal structure of di-bromo-meth-oxy-seselin (DBMS), a photobiologically active pyran-ocoumarin.

Project description:The title compound, C15H14Br2O4 [systematic name: rac-(9S,10R)-3,9-dibromo-10-methoxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2(8H)-one], is a pyran-ocoumarin derivative formed by the bromination of seselin, which is a naturally occurring angular pyran-ocoumarin isolated from the Indian herb Trachyspermum stictocarpum. In the mol-ecule, the benzo-pyran ring system is essentially planar, with a maximum deviation of 0.044 (2) Å for the O atom. The di-hydro-pyran ring is in a half-chair conformation and the four essentially planar atoms of this ring form a dihedral angle of 4.6 (2)° with the benzo-pyran ring system. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming chains propagating along [010]. In addition, π-π stacking inter-actions, with centroid-centroid distances of 3.902 (2) and 3.908 (2) Å, link the hydrogen-bonded chains into layers parallel to (001).

| S-EPMC5418804 | biostudies-literature

Crystal structure of (E)-N'-(5-bromo-2-hy-droxy-benzyl-idene)nicotinohydrazide monohydrate.

Project description:In the title compound, C13H10BrN3O2·H2O, the conformation about the azomethine double bond is E. The mol-ecule exists in the amido form with a C=O bond length of 1.229 (2) Å. There is an intra-molecular O-H⋯N hydrogen bond forming an S(6) ring motif. The whole mol-ecule is almost planar, with an r.m.s. deviation of 0.021 Å for all non-H atoms, and the dihedral angle between the planes of the pyridine and benzene rings is 0.74 (12)°. In the crystal, the water mol-ecule of crystallization links the organic mol-ecules via Ow-H⋯O, Ow-H⋯N and N-H⋯Ow hydrogen bonds and short C-H⋯Ow contacts, forming sheets lying parallel to (100). Within the sheets there is a weak π-π inter-action involving the pyridine and benzene rings [centroid-to-centroid distance = 3.8473 (15) Å]. The sheets are linked via C-H⋯Br inter-actions, forming a three-dimensional network.

| S-EPMC4518959 | biostudies-literature

Crystal structure of 3-(2,2-di-bromo-acet-yl)-4-hy-droxy-2H-chromen-2-one.

Project description:The title compound, C11H6Br2O4, is a new coumarin derivative obtained from the reaction of 3-acetyl-4-hy-droxy-2H-chromen-2-one with bromine in acetic acid. The hy-droxyl group in involved in an intra-molecular O-H?O hydrogen bond. In the crystal, ?-? inter-actions between the rings of the bicycle [inter-centroid distances = 3.498?(2) and 3.539?(2)?Å] pack mol-ecules into stacks along the b axis, and weak inter-molecular C-H?O hydrogen bonds further link these stacks into layers parallel to the ab plane.

| S-EPMC4384588 | biostudies-literature

Crystal structure of tetra-hydro-seselin, an angular pyran-ocoumarin.

Project description:In the title compound, tetra-hydro-seselin, C14H16O3, a pyran-ocoumarin [systematic name: 8,8-dimethyl-3,4,9,10-tetra-hydro-2H,8H-pyrano[2,3-f]chromen-2-one] obtained from the hydrogenation of seselin in the presence of Pd/C in MeOH at room temperature, the dihedral angle between the central benzene ring and the best planes of the outer fused ring systems are 6.20?(7) and 10.02?(8)°. In the crystal, mol-ecules show only very weak inter-molecular C-H?O inter-actions.

| S-EPMC5598830 | biostudies-other

Crystal structure of 4,6-dimethyl-2-{[3,4,5-trihy-droxy-6-(hy-droxy-meth-yl)tetra-hydro-2H-pyran-2-yl]sulfan-yl}nicotino-nitrile.

Project description:In the title compound, C14H18N2O5S, the C-S bond lengths are unequal, with S-Cglucose = 1.8016?(15)?Å and S-Cpyrid-yl = 1.7723?(13)?Å. The hydro-philic glucose residues lie in the regions z ? 0.25 and 0.75. Four classical hydrogen bonds link the mol-ecules to form layers parallel to the ab plane, from which the pyridyl rings project; pyridyl ring stacking parallel to the a axis links adjacent layers.

| S-EPMC5683506 | biostudies-literature

Crystal structure of hy-droxy scandium nitrate chloride.

Project description:Each Sc3+ ion in the title salt, di-?-hydroxido-bis-[tri-aqua-(nitrato-?2 O,O')scandium(III)] dichloride, [Sc2(NO3)2(OH)2(H2O)6]Cl2, is coordinated by a nitrate anion, two hydroxide ions and three water mol-ecules to generate a distorted penta-gonal-bipyramidal ScO7 coordination polyhedron. The complete {[(NO3)(?-OH)Sc(H2O)3]2}2+ ion is generated by crystallographic inversion symmetry. The nitrate anion binds in a bidentate fashion whereas the hydroxide ions are bridged between two Sc centers. Two charge-balancing Cl- ions are located in the outer sphere. In the extended structure, O-H?O and O-H?Cl hydrogen bonds connect the components into a three-dimensional network.

| S-EPMC6505614 | biostudies-literature

Crystal structure of N-hy-droxy-picolinamide monohydrate.

Project description:The crystal structure of the title compound, C6H6N2O2·H2O, consists of N-hy-droxy-picolinamide and water mol-ecules connected through O-H⋯O and N-H⋯N hydrogen bonds. The O-H⋯O inter-actions and π-π stacking inter-actions between the pyridine rings [centroid-centroid distance = 3.427 (1) Å] organize the components into columns extending along the b axis and the N-H⋯N hydrogen bonds link these columns into a two-dimensional framework parallel to (100). The N-hy-droxy-picolinamide mol-ecule adopts a strongly flattened conformation and only the O-H group H atom deviates significantly from the mol-ecule best plane. The dihedral angle between the hydroxamic group and the pyridine ring is 5.6 (2)°. The conformation about the hydroxamic group C-N bond is Z and that about the C-C bond between the pyridine and hydroxamic groups is E.

| S-EPMC4770983 | 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