Browse
Submit Data
Databases
API
Help

Dataset Information

9 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

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

ABSTRACT: 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.

SUBMITTER: Zhang XY

PROVIDER: S-EPMC4257222 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

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

Zhang Xu-Yang XY Liu Bing-Ni BN Wang Ping-Bao PB Liu Deng-Ke DK

Acta crystallographica. Section E, Structure reports online 20140924 Pt 10

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 crystall ...[more]

PMID: 25484705

Similar Datasets

4-Bromo-1H-pyrrole-2-carb-oxy-lic acid.

Project description:In the title compound, C(5)H(4)BrNO(2), the non-H atoms of the pyrrole ring and the Br atom are approximately coplanar, with an r.m.s. deviation from the best fit plane of 0.025?(6)?Å;. The dihedral angle between the plane of the carb-oxy group and this plane is 14.1?(2)°. In the crystal, O-H?O hydrogen bonds link the mol-ecules together, forming corrugated sheets parallel to the bc plane.

| S-EPMC3435710 | biostudies-literature

6-Bromo-1H-indole-3-carb-oxy-lic acid.

Project description:In the title mol-ecule, C(9)H(6)BrNO(2), the dihedral angle between the -COOH group and the ring system is 6 (4)°. In the crystal, pairs of O-H⋯O hydrogen bonds link the mol-ecules into inversion dimers and these dimers are connected via N-H⋯O hydrogen bonds to form layers parallel to the (-101) plane.

| S-EPMC3343983 | biostudies-literature

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

Project description: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].

| S-EPMC4571407 | biostudies-literature

Crystal structure of 4-{[(2,4-di-hydroxy-benzyl-idene)amino]-meth-yl}cyclo-hexane-carb-oxy-lic acid.

Project description:In the title compound, C15H19NO4, the cyclo-hexyl ring adopts a chair conformation with both exocyclic C-C bonds in equatorial orientations. The dihedral angle between the basal plane of cyclo-hexyl ring and the 2,4-di-hydroxy-benzaldehyde moiety is 84.13 (13)°. An intra-molecular O-H⋯N hydrogen bonds closes an S(6) ring. In the crystal, Oc-H⋯Op (c = carb-oxy-lic acid, p = phenol) hydrogen bonds link the mol-ecules into [100] C(13) chains whereas an Op-H⋯Oc hydrogen bond generates [101] C(15) chains. Together, these bonds generate (010) sheets incorporating R 2 (2)(20) loops. Weak C-H⋯O and C-H⋯π inter-actions also occur.

| S-EPMC4719941 | biostudies-literature

1-(tert-But-oxy-carbon-yl)piperidine-4-carb-oxy-lic acid.

Project description:In the title compound, C(11)H(19)NO(4), the piperidine ring adopts a chair conformation. In the crystal, mol-ecules are linked by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds, forming a layer parallel to the bc plane.

| S-EPMC3200981 | 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

Crystal structure of 5-[(4-carb-oxy-benz-yl)-oxy]isophthalic acid.

Project description:The mol-ecular shape of the title compound, C16H12O7, is bent around the central CH2-O bond. The two benzene rings are almost perpendicular to one another, making a dihedral angle of 87.78?(7)°. In the crystal, each mol-ecule is linked to three others by three pairs of O-H?O hydrogen bonds, forming undulating sheets parallel to the bc plane and enclosing R 2 (2)(8) ring motifs. The sheets are linked by C-H?O hydrogen bonds and C-H?? inter-actions, forming a three-dimensional network.

| S-EPMC4971877 | biostudies-literature

Crystal structure of 3-(3,4,5-tri-meth-oxy-phen-yl)-1,2,3,4-tetra-hydro-cyclo-penta[b]indole-2-carb-oxy-lic acid.

Project description:In the title compound, C21H21NO5, obtained from a Morita-Baylis-Hillman adduct, the hydrogenated five-membered ring adopts a shallow envelope conformation, with the C atom bearing the carb-oxy-lic acid substituent deviating by 0.237?(1)?Å from the mean plane of the other four atoms (r.m.s. deviation = 0.007?Å). The dihedral angle between the fused ring system (all atoms; r.m.s. deviation = 0.057?Å) and the pendant trimeth-oxy benzene ring is 66.65?(3)°. The C atoms of the meta-meth-oxy groups lie close to the plane of the benzene ring [deviations = 0.052?(1) and -0.083?(1)?Å], whereas the C atom of the para-meth-oxy group is significantly displaced [deviation = -1.289?(1)?Å]. In the crystal, carb-oxy-lic acid inversion dimers generate R 2 (2)(8) loops. The dimers are connected by N-H?O hydrogen bonds, forming [011] chains. A C-H?O inter-action is also observed.

| S-EPMC4459319 | biostudies-literature

4,4'-Bipyridine-2-(carb-oxy-methyl-sulfan-yl)pyridine-3-carb-oxy-lic acid (1/1).

Project description:In the title co-crystal, C(10)H(8)N(2)·C(8)H(7)NO(4)S, the formate group is coplanar with the pyridyl ring of the acid [dihedral angle = 6.2?(7)°], while the carb-oxy-methyl-sulfanyl group makes a C-S-C-C torsion angle of 70.2?(1)° with the pyridine ring. The dihedral angle between the pyridyl rings of the 4,4'-bipyridine mol-ecule is 27.4?(1)°. The acid and the 4,4'-bipyridine mol-ecules are involved in hydrogen bonding via carb-oxy-lic O and pyridyl N atoms. The structure is further consolidated by inter-molecular C-H?O hydrogen bonds, generating a three-dimensional network.

| S-EPMC3011421 | biostudies-literature

3-(4-Meth-oxy-phen-yl)-5-methylisoxazole-4-carb-oxy-lic acid.

Project description:In the title compound, C12H11NO4, the dihedral angle between the benzene and isoxazole rings is 42.52?(8)°. The carb-oxy-lic acid group is close to being coplanar with the isoxazole ring [dihedral angle = 5.3?(2)°]. In the crystal, inversion dimers linked by pairs of O-H?O hydrogen bonds generate R2(2)(8) loops.

| S-EPMC3588455 | biostudies-literature

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