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

ABSTRACT: The title compound, C(23)H(19)FN(2)O(3)S, a fused-pyrimidine derivative, displays dihedral angles between the thia-zole ring and the benzene ring and substituted benzene ring of 7.10?(14) and 3.48?(12)°, respectively. The dihydro-pyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z configuration.

SUBMITTER: Zhao CG

PROVIDER: S-EPMC3247408 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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

Zhao Cheng-Guang CG Hu Jie J Zhang Ya-Li YL Zhang Jing J Yang Shu-Lin SL

Acta crystallographica. Section E, Structure reports online 20111022 Pt 11

The title compound, C(23)H(19)FN(2)O(3)S, a fused-pyrimidine derivative, displays dihedral angles between the thia-zole ring and the benzene ring and substituted benzene ring of 7.10 (14) and 3.48 (12)°, respectively. The dihydro-pyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z configuration. ...[more]

PMID: 22220026

Similar Datasets

(2Z)-Ethyl 5-(4-methoxy-phen-yl)-7-methyl-3-oxo-2-(3,4,5-trimethoxy-benzyl-idene)-3,5-dihydro-2H-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:In the title compound, C(27)H(28)N(2)O(7)S, the dihedral angles between the thia-zole ring and the mono- and tris-ubstituted benzene rings are 87.8?(2) and 17.9?(3)°, respectively. The dihydro-pyrimidine ring adopts a flattened boat conformation. In the crystal structure, ?-? stacking occurs [centroid-centroid separation = 3.6611?(11)?Å].

| S-EPMC2968379 | biostudies-literature

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

Project description:In the structure of the title compound, C(22)H(21)N(3)O(3)S, the thia-zole ring forms dihedral angles of 88.83?(7) and 9.39?(9)°, respectively, with the benzene and pyrrole rings. The dihydro-pyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z conformation.

| S-EPMC3515200 | biostudies-literature

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

Project description:In the title compound, C(25)H(24)N(2)O(3)S, the dihedral angles between the thia-zole ring and the phenyl and substituted benzene rings are 84.91?(11) and 11.58?(10)°, respectively. The dihydro-pyrimidine ring adopts a flattened boat conformation. The olefinic double bond is in a Z configuration.

| S-EPMC3254473 | biostudies-other

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.

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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 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 π-π stacking inter-actions [centroid-centroid distance = 3.762 (2) Å] contribute to the crystal packing.

| S-EPMC2961005 | 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⋯π inter-actions and π-π 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

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 2-diethyl-amino-4-oxo-3,5-diphenyl-4,5-dihydro-3H-pyrrolo-[3,2-d]pyrimidine-7-carboxyl-ate.

Project description:In the title compound, C(25)H(26)N(4)O(3), the two fused pyrrolo-[3,2-d]pyrimidine rings form a dihedral angle of 3.7?(2)°. The two substituent phenyl rings are twisted with respect to the pyrrole and pyrimidine rings, making dihedral angles of 57.2?(2) and 69.0?(2)°, respectively. The ethyl and eth-oxy groups are disordered over two positions; the site occupancies are 0.53?(1) and 0.47?(1) for ethyl, and 0.63?(1) and 0.37?(1) for eth-oxy. The crystal packing features C-H?O hydrogen bonds.

| S-EPMC3254465 | biostudies-literature

Ethyl 5-(4-chloro-phen-yl)-2-[(Z)-(methoxy-carbon-yl)methyl-ene]-7-methyl-3-oxo-3,5-dihydro-2H-thia-zolo[3,2-a]pyrimi-dine-6-carboxyl-ate.

Project description:The title compound, C(19)H(17)ClN(2)O(5)S, was synthesized by the reaction of ethyl 6-(4-chloro-phen-yl)-2-mercapto-4-methyl-1,6-dihydro-pyrimidine-5-carboxyl-ate and dimethyl acetyl-ene-dicarboxyl-ate in methanol. In the mol-ecule, the nearly planar thia-zole ring, with a mean deviation from the plane of 0.0108?(3)?Å, is fused with a dihydro-pyrimidine ring in a flattened half-chair conformation.

| S-EPMC2968292 | biostudies-other

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