Browse
Submit Data
Databases
API
Help

Dataset Information

18 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Crystal structure of ethyl 5-(3-fluoro-phen-yl)-2-[(4-fluoro-phen-yl)methyl-idene]-7-methyl-3-oxo-2H,3H,5H-[1,3]thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

ABSTRACT: In the title mol-ecule, C23H18F2N2O3S, the pyrimidine ring is in a half-chair conformation and the 3-fluoro-phenyl group is in the axial position. The thia-zole ring (r.m.s. deviation = 0.0252?Å) forms dihedral angles of 84.8?(7) and 9.6?(7)° with the 3-fluoro-substituted and 4-fluoro-substituted benzene rings, respectively. In the crystal, weak C-H?F and C-H?O hydrogen bonds connect mol-ecules, forming zigzag chains along the b axis. In addition ?-? stacking inter-actions with a centroid-centroid distance of 3.7633?(9)?Å connect these chains into ladders via inversion-related 4-fluoro-phenyl groups.

SUBMITTER: Krishnamurthy MS

PROVIDER: S-EPMC4257247 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Crystal structure of ethyl 5-(3-fluoro-phen-yl)-2-[(4-fluoro-phen-yl)methyl-idene]-7-methyl-3-oxo-2H,3H,5H-[1,3]thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Krishnamurthy M S MS Nagarajaiah H H Begum Noor Shahina NS

Acta crystallographica. Section E, Structure reports online 20141024 Pt 11

In the title mol-ecule, C23H18F2N2O3S, the pyrimidine ring is in a half-chair conformation and the 3-fluoro-phenyl group is in the axial position. The thia-zole ring (r.m.s. deviation = 0.0252 Å) forms dihedral angles of 84.8 (7) and 9.6 (7)° with the 3-fluoro-substituted and 4-fluoro-substituted benzene rings, respectively. In the crystal, weak C-H⋯F and C-H⋯O hydrogen bonds connect mol-ecules, forming zigzag chains along the b axis. In addition π-π stacking inter-actions with a centroid-centro ...[more]

PMID: 25484821

Similar Datasets

Crystal structure of ethyl 2-(2-fluoro-benzyl-idene)-5-(4-fluoro-phen-yl)-7-methyl-3-oxo-2,3-di-hydro-5H-1,3-thia-zolo[3,2-a]pyrimidine-6-carb-oxy-late.

Project description:In the title mol-ecule, C23H18F2N2O3S, the 4-fluoro-substituted and 2-fluoro-substituted benzene rings form dihedral angles of 88.16?(8) and 23.1?(1)°, respectively, with the thia-zole ring. The pyrimidine ring adopts a flattened sofa conformation with the sp (3)-hydridized C atom forming the flap. In the crystal, pairs of weak C-H?O hydrogen bonds link mol-ecules related by twofold rotation axes, forming R (2) 2(10) rings, which are in turn linked by weak C-H?N inter-actions to form chains of rings along [010]. In addition, weak C-H??(arene) inter-actions link the chains into layers parallel to (001) and ?-? inter-actions with a centroid-centroid distance of 3.836?(10)?Å connect these layers into a three-dimensional network.

| S-EPMC4257371 | biostudies-literature

Methyl (2Z)-2-(2-fluoro-4-meth-oxy-benzyl-idene)-5-(4-meth-oxy-phen-yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:The asymmetric unit of the title compound, C(24)H(21)FN(2)O(5)S, consists of two crystallographically independent mol-ecules. In each mol-ecule, the central dihydro-pyrimidine ring is significantly puckered and adopts a conformation which is best described as an inter-mediate between a boat and a screw boat. The least-squares planes of the dihydro-pyrimidine rings are almost coplanar with the fluoro-substituted benzene rings, making dihedral angles of 9.04?(7) and 6.68?(7)°, and almost perpendicular to the meth-oxy-substituted benzene rings with dihedral angles of 89.23?(7) and 88.30?(7)°. In the mol-ecular structure, S(6) ring motifs are formed by C-H?O and C-H?S hydrogen bonds. In the crystal, mol-ecules are linked into a three-dimensional network by inter-molecular C-H?O and C-H?F hydrogen bonds. The crystal structure is further stabilized by a C-H?? inter-action.

| S-EPMC3212305 | biostudies-literature

Ethyl 3-eth-oxy-carbonyl-methyl-7-methyl-5-phenyl-5H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:In the title compound, C(20)H(22)N(2)O(4)S, the central pyrimidine ring incorporating a chiral C atom is significantly puckered and adopts a slight boat conformation with C atom bearing the phenyl ring and the N atom opposite displaced by 0.367?(2) and 0.107?(2)?Å, respectively, from the plane formed by the remaining ring atoms. The benzene ring is positioned axially to the pyrimidine ring, making a dihedral angle of 88.99?(5)°. The thia-zole ring is essentially planar (r.m.s. deviation = 0.0033?Å). In the crystal, pairs of C-H?O inter-actions result in centrosymmetric dimers with graph-set motifs R(1) (2)(7) and R(2) (2)(8). A weak C-H?? contact is also observed.

| S-EPMC3470232 | biostudies-literature

Crystal structure of ethyl 2-acetyl-3,7-dimethyl-5-(thio-phen-2-yl)-5H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:In the title compound, C17H18N2O3S2, the pyrimidine ring adopts a shallow sofa conformation, with the C atom bearing the axially-oriented thio-phene ring as the flap [deviation = 0.439 (3) Å]. The plane of the thio-phene ring lies almost normal to the pyrimidine ring, making a dihedral angle of 79.36 (19)°. In the crystal, pairs of very weak C-H⋯O hydrogen bonds link the mol-ecules related by twofold rotation axes, forming R 2 (2)(18) rings, which are in turn linked by another C-H⋯O inter-action, forming chains of rings along [010]. In addition, weak C-H⋯π(thio-phene) inter-actions link the chains into layers parallel to [001] and π-π inter-actions with a centroid-centroid distance of 3.772 (10) Å connect these layers into a three-dimensional network.

| S-EPMC4518970 | biostudies-literature

Methyl 5-(4-acet-oxy-phen-yl)-2-(2-bromo-benzyl-idine)-7-methyl-3-oxo-2,3-di-hydro-5H-1,3-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:In the title mol-ecule, C24H19BrN2O5S, the pyrimidine ring is in a flattened half-chair conformation and the 4-acet-oxy-phenyl group is substituted axially to this ring. The thia-zole ring is essentially planar [with a maximum deviation of 0.012?(2)?Å for the N atom] and forms dihedral angles of 17.65?(13) and 88.95?(11)° with the bromo- and acet-oxy-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 81.84?(13)?Å. In the crystal, pairs of weak C-H?O hydrogen bonds lead to the formation of inversion dimers. A weak C-H?? inter-action and ?-? stacking inter-actions with centroid-centroid distances of 3.5903?(14)?Å are observed.

| S-EPMC3793759 | biostudies-literature

Methyl 5-(4-hy-droxy-3-meth-oxy-phen-yl)-2-(4-meth-oxy-benzyl-idene)-7-methyl-3-oxo-2,3-dihydro-5H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:In the title compound, C(24)H(22)N(2)O(6)S, a pyrimidine ring substituted with 4-hy-droxy-3-meth-oxy-phenyl is fused with a thia-zole ring. The 4-hy-droxy-3-meth-oxy-phenyl group is positioned axially to the pyrimidine ring, making a dihedral angle 85.36?(7)°. The pyrimidine ring adopts a twist boat conformation. In the crystal, O-H?N inter-actions result in a chain running along the b axis. The carbonyl O atom bonded to the thia-zole ring is involved in two C-H?O hydrogen-bond inter-actions forming centrosymmetric dimers; the ten- and six-membered rings resulting from these inter-actions have R(2) (2)(10) and R(1) (2)(6) motifs, respectively.

| S-EPMC3239076 | biostudies-literature

Crystal structure of ethyl 4-(2,4-di-chloro-phen-yl)-2-methyl-4H-benzo[4,5]thia-zolo[3,2-a]pyrimidine-3-carboxyl-ate.

Project description:In the title compound, C20H16Cl2N2O2S, the pyrimidine ring has a screw-boat conformation. The attached di-chloro-phenyl ring is twisted at an angle of 89.29?(13)° with respect to the pyrimidine ring mean plane. The benzo-thia-zole group is approximately planar (r.m.s. deviation = 0.008?Å) and inclined to the pyrimidine ring mean plane by 3.04?(10)°. The carboxyl-ate group assumes an extended conformation with respect to the pyrimidine ring, which can be seen from the O=C-O-C torsion angle of 3.2?(4) °. In the crystal, mol-ecules are linked via C-H?O and C-H?N hydrogen bonds, forming slabs lying parallel to (100).

| S-EPMC4420040 | biostudies-literature

3-Bromo-2-[4-(methyl-sulfan-yl)phen-yl]-5,6,7,8-tetra-hydro-1,3-benzo-thia-zolo[3,2-a]imidazole.

Project description:In the title mol-ecule, C16H15BrN2S2, the central imidazo[2,1-b]thia-zole fragment is almost planar (r.m.s. deviation = 0.012?Å), and the fused 5,6,7,8-tetra-hydro-benzene ring adopts an unsymmetrical half-chair conformation. The dihedral angle between the imidazo[2,1-b]thia-zole and benzene planes is 18.25?(4)°. The terminal methyl-sulfanyl substituent lies practically within the benzene plane [the dihedral angle between the corresponding planes is 7.20?(10)°] and is turned toward the C-Br bond. In the crystal, mol-ecules form infinite chains along [100] via secondary Br?N inter-actions [3.1861?(16)?Å]. The chains are arranged at van der Waals distances.

| S-EPMC4011264 | biostudies-literature

Methyl 2-(2-bromo-benzyl-idene)-5-(4-hy-droxy-phen-yl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:In the title compound, C(22)H(17)BrN(2)O(4)S, the central dihydropyrimidine ring, with a chiral C atom, is significantly puckered and adopts a half-chair conformation with the chiral C atom displaced from the mean plane of the remaining ring atoms by 0.305?(6)?Å. The hydroxy-phenyl ring is positioned axially to the pyrimidine ring and almost bisects it, the dihedral angle between the mean-planes of the two rings being 89.78?(12)°. The meth-oxy-carbonyl group is disordered over two sites with an occupancy ratio of 0.568?(5):0.432?(5), resulting in a major and a minor conformer. In the crystal, O-H?N and C-H?S inter-actions result in sheets along the c axis. The supra-molecular assembly is stabilized by ?-? stacking inter-actions between the 2-bromo-benzyl-idene and thia-zolopyrimidine rings [centroid-centroid distance = 3.632?(1)?Å]. In addition, C-H?? inter-actions are also observed in the crystal structure.

| S-EPMC3344184 | biostudies-other

Crystal structure of (2-methyl-4-phenyl-4H-benzo[4,5]thia-zolo[3,2-a]pyrimidin-3-yl)(phen-yl)methanone.

Project description:In the title compound, C24H18N2OS, the pyrimidine ring has a flat envelope conformation with the methine C atom as the flap. The attached phenyl and benzoyl rings are inclined to the mean plane of the pyrimidine ring by 84.87?(8) and 75.33?(9)°, respectively. The benzo-thia-zolo group is planar (r.m.s. deviation = 0.009?Å) and inclined to the mean plane of the pyrimidine ring by 3.27?(6)°. In the crystal, mol-ecules are linked by pairs of C-H?N hydrogen bonds, forming inversion dimers.

| S-EPMC4420141 | 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