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

ABSTRACT: 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.

SUBMITTER: Asiri AM

PROVIDER: S-EPMC2968875 | biostudies-literature | 2009 Mar

REPOSITORIES: biostudies-literature

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

Asiri Abdullah Mohamed AM Akkurt Mehmet M Khan Islam Ullah IU Arshad Muhammad N MN

Acta crystallographica. Section E, Structure reports online 20090325 Pt 4

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- ...[more]

PMID: 21582561

Similar Datasets

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

Project description: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.

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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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(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].

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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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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. π-π 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⋯π inter-actions also occur.

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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 π-π 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%.

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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].

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

Project description:The asymmetric unit of the title compound, C(18)H(11)NO(2)S, contains two crystallographically independent mol-ecules. In one mol-ecule, the oxazole and thio-phene rings are oriented at dihedral angles of 17.40 (9) and 18.18 (7)° with respect to the naphthalene ring system, while the oxazole and thio-phene rings are oriented to each other at a dihedral angle of 0.86 (9)°. In the other mol-ecule, the corresponding angles are 3.05 (8), 9.62 (6) and 7.02 (8)°, respectively. In each mol-ecule, a weak intra-molecular C-H⋯N hydrogen bond links the oxazole N atom to the naphthalene group. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure. π-π stacking between the oxazole and thio-phene rings, between the thio-phene and naphthalene rings, and between the oxaozole and naphthalene rings, [centroid-centroid distances = 3.811 (2), 3.889 (2), 3.697 (2) and 3.525 (2) Å] may further stabilize the crystal structure.

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Crystal structure of 2-methyl-4-[(thio-phen-2-yl)methyl-idene]-1,3-oxazol-5(4H)-one.

Project description:The asymmetric unit of the title compound, C9H7NO2S, contains two crystallographically independent mol-ecules (A and B). Both mol-ecules are almost planar [maximum deviations = 0.047 (1) and 0.090 (1) Å, respectively, for the S atoms] with the oxazole and thio-phene rings being inclined to one another by 2.65 (16)° in mol-ecule A and by 4.55 (15)° in mol-ecule B. In the crystal, the individual mol-ecules are linked via C-H⋯O hydrogen bonds, forming -A-B-A-B- chains along the [10-1] direction. The chains are linked via C-H⋯π and π-π inter-actions [inter-centroid distances = 3.767 (2) and 3.867 (2) Å] involving inversion-related oxazole and thio-phene rings in both mol-ecules, forming a three-dimensional structure.

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