Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure of 4-oxo-4H-chromene-3-carb-oxy-lic acid.

ABSTRACT: In the title compound, C10H6O4, also known as 3-carb-oxy-chromone, the non-H atoms of the chromone ring are essentially coplanar (r.m.s. deviation = 0.0057 Å), with the maximum deviation from their least-squares plane [0.011 (2) Å] being for a pyran C atom. The dihedral angle between the fused ring and plane of the carb-oxy group is 3.06 (2)°. An intra-molecular hydrogen bond is formed between the ring carbonyl O atom and the carb-oxy O-H atom, closing an S(6) loop. In the crystal, mol-ecules are assembled by stacking inter-actions [centroid-centroid distance between the benzene and pyran rings = 3.844 (3) Å] and C-H⋯O hydrogen bonds, generating a three-dimensional network. Short contacts are also observed between the carb-oxy O and C atoms [C=O⋯C=O = 3.002 (3) Å].

SUBMITTER: Ishikawa Y

PROVIDER: S-EPMC4571407 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure of 4-oxo-4H-chromene-3-carb-oxy-lic acid.

Ishikawa Yoshinobu Y

Acta crystallographica. Section E, Crystallographic communications 20150717 Pt 8

In the title compound, C10H6O4, also known as 3-carb-oxy-chromone, the non-H atoms of the chromone ring are essentially coplanar (r.m.s. deviation = 0.0057 Å), with the maximum deviation from their least-squares plane [0.011 (2) Å] being for a pyran C atom. The dihedral angle between the fused ring and plane of the carb-oxy group is 3.06 (2)°. An intra-molecular hydrogen bond is formed between the ring carbonyl O atom and the carb-oxy O-H atom, closing an S(6) loop. In the crystal, mol-ecules ar ...[more]

PMID: 26396807

Similar Datasets

6-Chloro-4-oxo-4H-chromene-3-carb-aldehyde.

Project description:In the title compound, C10H5ClO3, a chlorinated 3-formyl-chromone derivative, the non-H atoms are essentially coplanar (r.m.s. deviation = 0.0456?Å) with the largest deviation from the least-squares plane [0.1136?(16)?Å] being found for the ring-bound carbonyl O atom. In the crystal, mol-ecules are linked through stacking inter-actions along the b axis [shortest centroid-centroid distance between the pyran and benzene rings = 3.4959?(15)?Å].

| S-EPMC4011265 | biostudies-literature

Crystal structure of benzene-1,3,5-tri-carb-oxy-lic acid-4-pyridone (1/3).

Project description:Slow co-crystallization of a solution of benzene-1,3,5-tri-carb-oxy-lic acid with a large excess of 4-hy-droxy-pyridine produces an inter-penetrating, three-dimensional, hydrogen-bonded framework consisting of three 4-pyridone and one benzene-1,3,5-tri-carb-oxy-lic acid mol-ecules, C9H6O6·3C5H5NO. This structure represents an ortho-rhom-bic polymorph of the previously reported C-centered, monoclinic structure [Campos-Gaxiola et al. (2014 ▸). Acta Cryst. E70, o453-o454].

| S-EPMC4644998 | biostudies-literature

6-Bromo-4-oxo-4H-chromene-3-carb-alde-hyde.

Project description:In the title compound, C10H5BrO3, a brominated 3-formyl-chromone derivative, the non-H atoms are essentially coplanar (r.m.s. deviation = 0.0420?Å), with the largest deviation from its mean plane [0.109?(2)?Å] being found for the ring-bound carbonyl O atom. In the crystal, mol-ecules are linked through halogen bonds [Br?O = 3.191?(2)?Å, C-Br?O = 167.32?(10)° and C=O?Br = 168.4?(2)°] along [101]. Mol-ecules are assembled into layers parallel to (101) via ?-? stacking inter-actions along the b axis [shortest centroid-centroid distance between the pyran and benzene rings = 3.495?(2)?Å].

| S-EPMC4011302 | biostudies-literature

Crystal structure of 8-bromo-4-oxo-4H-chromene-3-carbaldehyde.

Project description:In the title compound, C10H5BrO3, a brominated 3-formyl-chromone, all atoms are essentially coplanar (r.m.s. = 0.0104 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.028 (5) Å] being for one of the benzene C atoms. In the crystal, mol-ecules are linked through C-H⋯O hydrogen bonds, which are further assembled by face-to-face π-π stacking inter-actions [centroid-centroid distance between the pyran rings = 3.854 (4) Å]. Shorter contacts than the sum of van der Waals radii are observed between the Br and formyl O atoms [Br⋯O = 3.046 (4) Å, C-Br⋯O = 175.23 (18)° and Br⋯O-C = 132.6 (3)°], features that do indicate halogen bonding.

| S-EPMC4571403 | biostudies-literature

Crystal structure of 7-bromo-4-oxo-4H-chromene-3-carbaldehyde.

Project description:In the title compound, C10H5BrO3, a brominated 3-formyl-chromone derivative, all atoms are essentially coplanar (r.m.s. = 0.0631 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.215 (3) Å] being for the formyl O atom. In the crystal, mol-ecules are linked into tapes through C-H⋯O hydrogen bonds and these tapes are assembled by stacking inter-actions [centroid-centroid distance between the pyran rings = 3.858 (3) Å] to form supra-molecular layers that stack along the c axis.

| S-EPMC4186120 | biostudies-literature

Crystal structure of a 2:1 co-crystal of meloxicam with acetyl-endi-carb-oxy-lic acid.

Project description:The pharmaceutical 2:1 co-crystal of meloxicam [MXM; systematic name: 4-hy-droxy-2-methyl-N-(5-methyl-thia-zol-2-yl)-2H-1,2-benzo-thia-zine-3-carboxamide 1,1-dioxide] with acetyl-enedi-carb-oxy-lic acid (ACA; systematic name: but-2-ynedioic acid), crystallizes with one MXM mol-ecule and half an ACA mol-ecule in the asymmetric unit, C14H13N3O4S2·0.5C4H2O4. The mid-point of the triple bond of ACA is located on an inversion centre. In the crystal, the two stereoisomers of MXM with respect to the N atom of the sulfonamide group are related by the inversion centre. The carbonyl and hy-droxy groups belonging to the MXM mol-ecule are involved in an intra-molecular O-H?O hydrogen bond. The structure-forming motif includes two MXM mol-ecules linked via an ACA conformer through N-H?O and O-H?N hydrogen bonds, similar to MXM co-crystals with other di-carb-oxy-lic acids.

| S-EPMC5137627 | biostudies-literature

Crystal structure of 9-(4-bromo-but-yl)-9H-fluorene-9-carb-oxy-lic acid.

Project description:The title compound, C18H17BrO2, is a key inter-mediate in the synthesis of lomitapide mesylate, a microsomal triglyceride transfer protein inhibitor. Its asymmetric unit contains two independent mol-ecules with slightly different conformations; the mean planes of the 4-bromo-butyl and carboxyl-ate groups in the two mol-ecules form dihedral angles of 24.54?(12) and 17.10?(18)°. In the crystal, carboxyl-ate groups are involved in O-H?O hydrogen bonding, which leads to the formation of two crystallographically independent centrosymmetric dimers. Weak inter-molecular C-H?O inter-actions further link these dimers into layers parallel to the bc plane.

| S-EPMC4257222 | biostudies-literature

Crystal structure of [1,1':3',1''-ter-phenyl]-2',3,3''-tri-carb-oxy-lic acid.

Project description:The asymmetric unit of the title compound, C21H14O6, com-prises two symmetrically independent mol-ecules that form a locally centrosymmetric hydrogen-bonded dimer, with the planes of the corresponding carb-oxy-lic acid groups rotated by 15.8 (1) and 17.5 (1)° relative to those of the adjacent benzene rings. The crystal as a whole, however, exhibits a noncentrosymmetric packing, described by the polar space group Pca21. The dimers form layers along the ab plane, being inter-connected by hydrogen bonds involving the remaining carb-oxy-lic acid groups. The plane of the central carb-oxy-lic acid group forms dihedral angles of 62.5 (1) and 63.0 (1)° with those of the adjacent benzene rings and functions as a hydrogen-bond donor and acceptor. As a donor, it inter-connects adjacent layers, while as an acceptor it stabilizes the packing within the layers. The 'distal' carb-oxy-lic acid groups are nearly coplanar with the planes of the adjacent benzene rings, forming dihedral angles of 1.8 (1) and 7.1 (1)°. These groups also form intra- and inter-layer hydrogen bonds, but with 'reversed' functionality, as compared with the central carb-oxy-lic acid groups.

| S-EPMC4555404 | biostudies-literature

Pyrimidine-4-carb-oxy-lic acid.

Project description:The crystal structure of the title compound, C5H4N2O2, is built of acid mol-ecules located on a mirror plane. They form sheets stacked along the b-axis direction. The mol-ecules inter-act via O-H⋯N hydrogen bonds, forming [001] chains, and weak van der Waals inter-actions.

| S-EPMC3685042 | biostudies-literature

3-Carb-oxy-methyl-1H-indole-4-carb-oxy-lic acid.

Project description:In the title compound, C(11)H(9)NO(4), the carboxyl group bonded to the six-membered ring lies close to the plane of the 1H-indole ring system [dihedral angle = 13.13?(9)°], whereas the carb-oxy-lic acid group linked to the five-membered ring by a methyl-ene bridge is close to perpendicular [78.85?(9)°]. In the crystal, O-H?O and N-H?O hydrogen bonds link the mol-ecules, generating (110) sheets.

| S-EPMC3254489 | 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