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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.

ABSTRACT: 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.

SUBMITTER: Jotani MM

PROVIDER: S-EPMC2983585 | BioStudies | 2010-01-01T00:00:00Z

REPOSITORIES: biostudies

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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.

2011-01-01 | S-EPMC3239076 | BioStudies

Crystal structure of 2-acetyl-5-(3-methoxyphenyl)-3,7-dimethyl-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate.

Project description:In the title mol-ecule, C20H22N2O4S, the pyrimidine ring is in a flattened half-chair conformation and the 3-meth-oxyphenyl substituent is in an axial arrangement. The thia-zole ring forms a dihedral angle of 81.3?(1)° with the benzene ring. In the crystal, weak C-H?S inter-actions link mol-ecules into chains along [001]. In addition, there are ?-? inter-actions between inversion-related thia-zole rings with a centroid-centroid distance of 3.529?(2)?Å. The ethyl group was refined as disordered over two sets of sites with an occupancy ratio of 0.52?(3):0.48?(2).

1000-01-01 | S-EPMC4257338 | BioStudies

Crystal structure of ethyl 4-(2-chloro-phen-yl)-2-methyl-4H-pyrimido[2,1-b][1,3]benzo-thia-zole-3-carboxyl-ate.

Project description:In the title compound, C20H17ClN2O2S, the dihedral angle between the planes of the benzo-thia-zole fused ring system (r.m.s. deviation = 0.024?Å) and the chloro-benzene ring is 89.62?(12)°. The ester C-O-C-C side chain has an anti orientation [torsion angle = -155.2?(3)°]. In the crystal, weak aromatic ?-? stacking inter-actions are observed between the phenyl and pyrimidine rings [centroid-centroid seperation = 3.666?(2)?Å].

2015-01-01 | S-EPMC4555405 | BioStudies

(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].

2009-01-01 | S-EPMC2968379 | BioStudies

Crystal structure of ethyl 2-cyano-3-[(1-eth-oxy-ethyl-idene)amino]-5-(3-meth-oxy-phen-yl)-7-methyl-5H-1,3-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

Project description:In the title compound, C22H24N4O4S, the central pyrimidine ring adopts a sofa conformation with the ring-junction N atom displaced by 0.2358?(6)?Å from the mean plane of the remaining ring atoms. The 3-meth-oxy-phenyl ring, at the chiral C atom opposite the other N atom, is positioned axially and is inclined to the thia-zolo-pyrimidine ring with a dihedral angle of 83.88?(7)°. The thia-zole ring is essentially planar (r.m.s. deviation = 0.0034?Å). In the crystal, pairs of weak C-H?O hydrogen bonds link mol-ecules related by twofold rotation axes to form R 2 (2)(8) rings, which in turn are linked by weak C-H?N inter-actions, forming ribbons along [-110]. In addition, ?-? stacking inter-actions [centroid-centroid distance = 3.5744?(15)?Å] connect the ribbons, forming slabs lying parallel to (001).

1000-01-01 | S-EPMC4438835 | BioStudies

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.

2013-01-01 | S-EPMC3793759 | BioStudies

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.

2012-01-01 | S-EPMC3470232 | BioStudies

3-{2-[2-(2-Fluoro-benzyl-idene)hydrazin-yl]-1,3-thia-zol-4-yl}-2H-chromen-2-one.

Project description:In the title compound, C(19)H(12)FN(3)O(2)S, the chromene ring system and the thia-zole ring are approximately planar [maximum deviations of 0.023?(3)?Å and 0.004?(2)?Å, respectively]. The chromene ring system is inclined at angles of 4.78?(10) and 26.51?(10)° with respect to the thia-zole and benzene rings, respectively, while the thia-zole ring makes a dihedral angle of 23.07?(12)° with the benzene ring. The mol-ecular structure is stabilized by an intra-molecular C-H?O hydrogen bond, which generates an S(6) ring motif. The crystal packing is consolidated by inter-molecular N-H?O hydrogen bonds, which link the mol-ecules into chains parallel to [100], and by C-H?? and ?-? [centroid-centroid distance = 3.4954?(15)?Å] stacking inter-actions.

2010-01-01 | S-EPMC2979535 | BioStudies

(Z)-3-(2-{2-[1-(4-Hy-droxy-phen-yl)ethyl-idene]hydrazin-1-yl}-1,3-thia-zol-4-yl)-2H-chromen-2-one.

Project description:In the title compound, C(20)H(15)N(3)O(3)S, an intra-molecular C-H?O hydrogen bond generates an S(6) ring motif. The chromene ring system is inclined at dihedral angles of 14.21?(9) and 9.91?(10)°, respectively, with respect to the thia-zole and benzene rings. The thia-zole ring makes a dihedral angle of 24.06?(11)° with the benzene ring. In the crystal structure, O-H?O hydrogen bonds link the mol-ecules into a zigzag chain along [20]. Weak N-H?O and C-H?O inter-actions connect the chains into a three-dimensional network. ?-? stacking inter-actions with a centroid-centroid distance of 3.4209?(14)?Å are also observed between the chains.

1000-01-01 | S-EPMC3006946 | BioStudies

Crystal structure of bis-[2-(benzo-thia-zol-2-yl)phenolato-?(2) N,O]copper(II).

Project description:In the title complex, [Cu(C13H8NOS)2], the Cu(II) atom is coordinated by two N atoms and two O atoms from two bidentate benzo-thia-zolphenolate ligands, forming a distorted tetra-hedral geometry [dihedral angle between two N-Cu-O planes: 45.1?(2)°]. The dihedral angles between the benzo-thia-zole ring systems and the phenol rings are 4.1?(4) and 5.8?(4)°, indicating an almost planar geometry. Weak intra- and inter-molecular C-H?O hydrogen bonds are observed. In the crystal, weak ?-? inter-actions between aromatic and thia-zole rings [centroid-centroid distances = 3.626?(3) and 3.873?(3)?Å] link the mol-ecules into a two-dimensional supra-molecular network along the bc plane.

1000-01-01 | S-EPMC4555420 | BioStudies

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