Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

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

ABSTRACT: 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.

SUBMITTER: Nagarajaiah H

PROVIDER: S-EPMC3470232 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

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

Nagarajaiah H H Begum Noor Shahina NS

Acta crystallographica. Section E, Structure reports online 20120908 Pt 10

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 ...[more]

PMID: 23125676

Similar Datasets

Ethyl 2-(2-acetoxy-benzyl-idene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:In the title mol-ecule, C(25)H(22)N(2)O(5)S, the atoms of the thia-zolopyrimidine ring system, with the exception of the phenyl-bearing C atom [deviation = 0.177?(2)?Å], are essentially planar [r.m.s deviation = 0.100?(2) °] and the mean plane of these atoms forms dihedral angles of 89.86?(10) and 7.97?(8)° with the phenyl and benzene rings, respectively. In the crystal, co-operative C-H?O and C-H?? inter-actions lead to a supra-molecular chain along the a axis. These chains are connected via ?-? inter-actions [centroid-centroid = 3.7523?(13)?Å].

| S-EPMC2983806 | biostudies-literature

Ethyl (2Z)-2-(3-methoxy-benzyl-idene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:In the title compound, C(24)H(22)N(2)O(4)S, the central pyrimidine ring is significantly puckered, assuming a conformation inter-mediate between a boat and a screw boat. The nearly planar thia-zole ring (r.m.s. deviation = 0.0258?Å) is fused with the pyriamidine ring, making a dihedral angle of 9.83?(7)°. The carboxyl group is in an extended conformation with an anti-periplanar orientation with respect to the dihydropyrimidine ring. The benzene ring linked at the chiral C atom is perpendicular to the pyrimidine ring [dihedral angle = 85.21?(8)°] whereas the phenyl ring is nearly coplanar, making a dihedral angle of 13.20?(8)°. An intra-molecular C-H?S hydrogen bond is observed. The crystal packing is influenced by weak inter-molecular C-H?? inter-actions and ?-? stacking between the thia-zole and phenyl rings [centroid-centroid distance = 3.9656?(10)?Å], which stack the mol-ecules along the c axis.

| S-EPMC2983585 | biostudies-literature

Ethyl 2-[(Z)-3-chloro-benzyl-idene]-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-1,3-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:In the title compound, C(23)H(19)ClN(2)O(3)S, the central pyrimidine ring is significantly puckered, assuming almost a screw boat conformation. In addition to the usual inter-molecular C-H?O hydrogen bonding, short intra-molecular C-H?S contacts and ?-? stacking inter-actions [centroid-centroid distance = 3.762?(2)?Å] contribute to the crystal packing.

| S-EPMC2961005 | 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 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.

Project description: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.

| S-EPMC4257247 | 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 7-methyl-3-oxo-5-phenyl-2-(2,4,6-trimeth-oxy-benzyl-idene)-2,3-dihydro-5H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:In the title compound, C(26)H(26)N(2)O(6)S, the benzene ring is positioned axially to the thia-zolopyrimidine ring and bis-ects it with a dihedral angle of 80.94?(7)°. The pyrimidine ring adopts a flattened boat conformation. In the crystal, pairs of bifurcated C-H?O hydrogen bonds link the mol-ecules into chains along the c axis.

| S-EPMC3344148 | biostudies-other

Ethyl 2-(4-carb-oxy-benzyl-idene)-7-methyl-3-oxo-5-phenyl-2,3-dihydro-5H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate-N,N-dimethyl-formamide (1/1).

Project description:In the title compound, C(24)H(20)N(2)O(5)S·C(3)H(7)NO, a benzene ring is positioned axially to the pyrimidine ring, which adopts a twist-boat conformation, and is inclined to its mean plane by 85.36?(7)°. In the crystal, inter-molecular C-H?O inter-actions result in centrosymmetric head-to-head dimers with an R(2) (2)(14) graph-set motif along the b axis. Pairs of C-H?O and O-H?O hydrogen bonds form centrosymmetric head-to-head dimers about inversion centres, corresponding to an R(2) (2)(7) graph-set motif along the a axis.

| S-EPMC3275196 | 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