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(4Z)-4-Benzyl-idene-2-phenyl-1,3-oxazol-5(4H)-one.

ABSTRACT: In the title compound, C(17)H(13)NO(2), the benzene ring is twisted slightly out of the plane of the oxazole ring to which it is attached [dihedral angle = 7.98 (8)°]. Similarly, there is a twist [dihedral angle = 5.50 (8)°] between the oxazole and phenyl rings that are linked via the C=C bond [1.348 (2) Å]; the conformation about the latter is Z. In the crystal, the presence of C-H⋯O, C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.5259 (9) Å] link the mol-ecules into a three-dimensional architecture.

SUBMITTER: Asiri AM

PROVIDER: S-EPMC3344097 | biostudies-literature |

REPOSITORIES: biostudies-literature

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2-Phenyl-4-(3,4,5-trimethoxy-benzyl-idene)-1,3-oxazol-5(4H)-one.

Project description:The title compound, C(19)H(17)NO(5), was synthesized as part of a continuing project involving the structures of oxazolone derivatives. The mol-ecule adopts a Z configuration about the central olefinic bond. The 2-phenyl ring is slightly twisted out of the plane of the oxazolone ring system by 11.2 (2)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

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4-(2-Methoxy-benzyl-idene)-2-phenyl-1,3-oxazol-5(4H)-one.

Project description:The title mol-ecule, C(17)H(13)NO(3), adopts a Z configuration about the central olefinic bond. The 2-phenyl ring is almost coplanar with the plane of the oxazolone ring system, making a dihedral angle of 2.03 (11)°. The crystal structure is stabilized by π-π inter-actions between the oxazolone ring and phenyl ring of a neighbouring mol-ecule [centroid-centroid distance = 3.550 (3)Å], and by two weak inter-molecular C-H⋯π inter-actions. In addition, the crystal structure exhibits one weak intra-molecular C-H⋯N hydrogen bond.

| S-EPMC2968875 | biostudies-literature

(E)-4-(2,5-Dimethoxy-benzyl-idene)-2-phenyl-1,3-oxazol-5(4H)-one.

Project description:The central aza-lactone ring in the title compound, C(18)H(15)NO(4), is planar (r.m.s. deviation 0.05, 0.12?Å) in both independent mol-ecules comprising the asymmetric unit. The benzyl-idene substituent is coplanar with this ring [dihedral angle between the planes = 1.8?(1)° in the first mol-ecule and 2.8?(1)° in the second], as is the phenyl substitutent [dihedral angle between rings = 4.6?(1) and 9.7?(1)°, respectively].

| S-EPMC2977274 | biostudies-literature

4-[(3-Meth-oxy-anilino)methyl-idene]-2-phenyl-1,3-oxazol-5(4H)-one.

Project description:In the title compound, C(17)H(14)N(2)O(3), the oxazolone ring is essentially planar [maximum deviation = 0.004 (1) Å] and is oriented with respect to the phenyl and benzene rings at 10.06 (9) and 5.63 (8)°, respectively; the dihedral angle between the phenyl ring and the benzene ring is 15.69 (8)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains running along the a axis. Neighbouring chains are inter-connected by π-π stacking, the centroid-centroid distance being 3.6201 (9) Å.

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Ortho-rhom-bic modification of (E)-4-benzyl-idene-2-phenyl-1,3-oxazol-5(4H)-one: whole mol-ecule disorder.

Project description:The title mol-ecule, C(16)H(11)NO(2), is disordered about a pseudo-twofold rotation axis that approximately bis-ects the mol-ecule along the C=O double bond. The two overlapping components are planar [r.m.s. deviation = 0.10?Å in the major 0.537?(4) component and 0.07?Å in the minor component]. The two components are aligned at 1.8?(3)°.

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4-{[(4Z)-5-Oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl-idene]meth-yl}phenyl acetate.

Project description:The title mol-ecule, C(18)H(13)NO(4), shows a dihedral angle between the terminal acetyl group (r.m.s. deviation = 0.0081?Å) and remaining non-H atoms (r.m.s. = 0.0734?Å) of 53.45?(7)°. The configuration about the central olefinic bond is Z and overall the mol-ecule has a U-shaped conformation. Supra-molecular chains along the b-axis direction are found in the crystal structure. These are stabilized by (C=O)??(ring centroid of the 1,3-oxazole ring) inter-actions [3.370?(2)?Å].

| S-EPMC2979071 | biostudies-literature

2-(Naphthalen-1-yl)-4-(naphthalen-1-yl-methyl-idene)-1,3-oxazol-5(4H)-one.

Project description:In the title compound, C(24)H(15)NO(2), the oxazole ring is oriented at dihedral angles of 10.09?(4) and 6.04?(4)° with respect to the mean planes of the naphthalene ring systems, while the two naphthalene ring systems make a dihedral angle of 4.32?(3)°. Intra-molecular C-H?N hydrogen bonds link the oxazole N atom to the naphthalene ring systems. In the crystal, inter-molecular weak C-H?O hydrogen bonds link the mol-ecules into centrosymmetric dimers. ?-? contacts between the oxazole and naphthalene rings and between the naphthalene ring systems [centroid-centroid distances = 3.5947?(9) and 3.7981?(9)?Å] may further stabilize the crystal structure. Three weak C-H?? inter-actions also occur.

| S-EPMC3089157 | biostudies-literature

4-[(Dimethyl-amino)methyl-idene]-2-(4-nitro-phen-yl)-1,3-oxazol-5(4H)-one.

Project description:The title mol-ecule, C(12)H(11)N(3)O(4), is essentially planar, the r.m.s. deviation for all non-H atoms being 0.068?Å. An intra-molecular C-H?N hydrogen bond occurs. The crystal packing is dominated by ?-? inter-actions [shortest centroid-centroid distance = 3.6312?(16)?Å], which lead to supra-molecular chains that are linked into a three-dimensional network via C-H?O contacts. The crystal was found to be a non-merohedral twin (twin law -1 0 0/0 -1 0/ 0.784 0 1), the fractional contribution of the minor component being approx-imately 22%.

| S-EPMC2979566 | biostudies-literature

(4Z,6Z)-4,6-Bis(4-meth-oxy-benzyl-idene)-2,2-dimethyl-1,3-dioxan-5-one.

Project description:The title compound, C(22)H(22)O(5), crystallizes with two independent mol-ecules in the asymmetric unit, both of which possess pseudo-C(s) symmetry. The central 1,3-dioxanone rings have envelope conformations, with the C atom bearing the two methyl groups at the flap. The benzene rings of the meth-oxy-benzyl-idene units, attached in the 4- and 6-positions on the central 1,3-dioxanone rings, are tilted in the same direction with dihedral angles varying between 8.2?(1) and 18.1?(1)°. The crystal packing is influenced by ?-stacking inter-actions of the parallel displaced type [centroid-centroid distance of 3.723?(1)?Å for mol-ecule 1 and 3.884?(1)?Å for mol-ecule 2, with ring slippages of 1.432 and 1.613?Å, respectively] and the T-shaped type, with the long mol-ecular axes all aligned along [010].

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5-Benzyl-idene-3-phenyl-2-phenyl-imino-1,3-thia-zolidin-4-one.

Project description:The title compound, C(22)H(16)N(2)OS, is a chalcone analog with a thia-zolidinone core that was synthesized as a potential cytotoxic and anti-cancer agent. The structure is commensurately modulated by unit-cell doubling along the direction of the a axis of the cell. The two crystallographically independent mol-ecules are differerentiated by the dihedral angle between the mean planes of the benzyl-idene phenyl group against the thia-zolidin-4-one moiety, which is 5.01 (7)° in one mol-ecule, and 17.41 (6)° in the other. The two mol-ecules are otherwise close to being indistinguishable and are related by crystallographic pseudo-translation. The two mol-ecules are not planar but are slightly bent with the benzyl-idene and phenyl-imino substituents being bent upwards with respect to the center planes of the two mol-ecules. The degree of bending of the two halves of the thia-zolidin-4-one moieties (defined as the planes that inter-sect at the S atom) are 11.08 (7) and 15.88 (7)°. Packing of the mol-ecules is facilitated by C-H⋯π inter-actions and slipped π-π stacking between one of the phenyl rings and a neighboring ethylene π system [distance between the centroid of the ethylene group and the closest phenyl C atom = 3.267 (2) Å, Cg(phenyl)⋯Cg(ethylene) = 3.926 Å].

| S-EPMC3152016 | biostudies-literature

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