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Absolute configuration of (1S,2S)-3-methyl-2-phenyl-2,3-dihydro-thia-zolo[2,3-b]quinazolin-5-one.

ABSTRACT: The absolute structure of the molecule in the crystal of the title compound, C(17)H(14)N(2)OS, was determined by the refinement of the Flack parameter to 0.0 (2) based on 1011 Friedel pairs. The quinazoline ring is essentially planar, with a maximum deviation of 0.037 (2) Å. The thia-zole ring is distorted from planarity [maximum deviation = 0.168 (2) Å] and adopts a slightly twisted envelope conformation, with the C atom as the flap atom. The central thia-zole ring makes dihedral angles of 7.01 (8) and 76.80 (10)° with the quinazoline and phenyl rings, respectively. The corresponding angle between the quinazoline and phenyl rings is 3.74 (9)°. In the crystal, there are no classical hydrogen bonds but stabilization is provided by weak C-H⋯π inter-actions, involving the centroids of the phenyl rings.

SUBMITTER: Ghorab MM

PROVIDER: S-EPMC3343911 | biostudies-literature |

REPOSITORIES: biostudies-literature

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7-Chloro-3-phenyl-benzo[4,5]thia-zolo[2,3-c][1,2,4]triazole.

Project description:In the title compound, C(14)H(8)ClN(3)S, the dihedral angle between the approximately planar triple-fused ring system (r.m.s. deviation = 0.065?Å) and the pendant phenyl ring is 62.25?(5)°. In the crystal, mol-ecules are linked into infinite chains along the c-axis direction by C-H?N hydrogen bonds. Aromatic ?-? stacking inter-actions [centroid-centroid distances = 3.7499?(8) and 3.5644?(8)?Å] and weak C-H?? inter-actions are also observed.

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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 (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.

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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.

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Project description:The relative and absolute configurations of the title compound, C(26)H(28)O(3)Se, were assigned from the known configuration of (R)-(-)-2-meth-oxy-2-(1-naphth-yl)propionic acid used as starting material, and by examination of the Bijvoet (Friedel) pairs, using the anomalous dispersion data collected with Mo K? radiation at low temperature. The geometry around the carbonyl group exists in the syn conformation, as reflected in torsion angles involving this group, and the stability of the structure is affected by weak bifurcated intra-molecular C-H?O hydrogen bonds.

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(5R*,11R*)-5-Methyl-1,2-dihydro-5,11-methano-5H,11H-1,3-thia-zolo[2,3-d][1,3,5]benzoxadiazo-cine.

Project description:The title compound, C(13)H(14)N(2)OS, crystallizes as a racemate in a non-chiral space group. It represents a conformationally restricted analogue of so-called Biginelli compounds known to exhibit multiple pharmacological activities and was selected for a single-crystal X-ray analysis in order to probe the chemical and spatial requirements of some kinds of activity. It was found that the state of hybridization of the formally aminic nitro-gen of the heterocycle is between sp(2) and sp(3) with the lone-pair electrons partially delocalized through conjugation with the sulfur atom rather than the double bond of the pyrimidine nucleus. As a result, the thia-zolo ring adopts a flat-envelope conformation and the puckering of the central pyrimidine ring is close to a half-chair. The critical phenyl ring is fixed in a pseudo-axial and perpendicular [dihedral angle 84.6?(1)°] orientation with respect to the pyrimidine ring via an oxygen bridge.

| S-EPMC2971350 | biostudies-literature

2,2,7-Trimethyl-2,3-dihydro-quinazolin-4(1H)-one.

Project description:There are two independent mol-ecules in the the asymmetric unit of the title compound, C(11)H(14)N(2)O. The heterocyclic ring of the bicyclic system has a sofa conformation, with the C atom bearing the two methyl groups displaced by 0.541?(7)?Å from the rest of the atoms of the ring [planar to within 0.064?(9)?Å]. Mol-ecules are linked into centrosymmetric dimers via N-H?O hydrogen bonds.

| S-EPMC2969724 | biostudies-literature

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

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

2-(2-{[4-Oxo-3-(2-phenyl-eth-yl)-3,4-dihydro-quinazolin-2-yl]sulfan-yl}eth-yl)-2,3-dihydro-1H-isoindole-1,3-dione.

Project description:In the title compound, C(26)H(21)N(3)O(3)S, the quinazolinyl group is essentially planar [r.m.s. deviation for the 10 non-H atoms = 0.057?Å]. The isoindoline-1,3-dione group is linked by an SCH(2)CH(2) chain to the pyrimidinyl C atom that lies between the two N atoms. Also, the phenyl group is linked by a CH(2)CH(2) chain at the N atom adjacent to the carbonyl group. This results in a conformation with these substituents lying to either side of the central quinazolinyl unit, with the former being approximately parallel [dihedral angle = 4.93?(7)°], and the phenyl group being inclined [dihedral angle = 71.61?(9)°] to the central quinazolinyl fused-ring system. In the crystal, mol-ecules are consolidated into a three-dimensional architecture by C-H?O inter-actions, involving all three carbonyl-O atoms, and ?-? inter-actions occurring between the pyrimidinyl and isoindole-benzene rings [inter-centroid distance = 3.5330?(13)?Å].

| S-EPMC3393323 | biostudies-literature

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