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Crystal structures of three 1-oxo-1,2-dihydronaphthalene derivatives: dimethyl 4-(4-methoxyphenyl)-2-(4-methylphenyl)-1-oxo-1,2-dihydronaphthalene-2,3-dicarboxylate, dimethyl 1-oxo-2-(pyren-4-yl)-4-(thiophen-2-yl)-1,2-dihydronaphthalene-2,3-dicarboxylate and ethyl 1-oxo-2-phenyl-2,4-bis(thiophen-2-yl)-1,2-dihydronaphthalene-3-carboxylate
In the title 1-oxo-1,2-dihydronaphthalene derivatives, C(28)H(24)O(6), (I), C(34)H(22)O(5)S, (II), and C(27)H(20)O(3)S(2), (III), the cyclohexa-1,3-diene rings of the 1,2-dihydronaphthalene ring systems adopt half-chair, boat and half-chair conformations, respectively. The carbonyl O atoms atta...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5290560/ https://www.ncbi.nlm.nih.gov/pubmed/28217337 http://dx.doi.org/10.1107/S2056989017000469 |
Sumario: | In the title 1-oxo-1,2-dihydronaphthalene derivatives, C(28)H(24)O(6), (I), C(34)H(22)O(5)S, (II), and C(27)H(20)O(3)S(2), (III), the cyclohexa-1,3-diene rings of the 1,2-dihydronaphthalene ring systems adopt half-chair, boat and half-chair conformations, respectively. The carbonyl O atoms attached to the dihydronaphthalene ring systems are each significantly deviated from the mean plane of the 1,2-dihydronaphthalene ring system, by 0.6162 (12) Å in (I), 0.6016 (16) Å in (II) and 0.515 (3) Å in (III). The mean planes of the 1,2-dihydronaphthalene ring systems make dihedral angles of 85.83 (3), 88.19 (3) and 81.67 (8)°, respectively, with the methylphenyl ring in (I), the pyrene ring in (II) and the phenyl ring in (III). In (I), the molecular structure is stabilized by an intramolecular C—H⋯O hydrogen bond, generating an S(6) ring motif. In the crystal of (I), molecules are linked by an intermolecular C—H⋯O hydrogen bond, which generates a C(8) zigzag chain running along [100]. Adjacent chains are further connected by C—H⋯π and offset π–π interactions [centroid–centroid distance = 3.6572 (9) Å], forming a double-chain structure. In the crystals of (II) and (III), molecules are linked into chain structures by offset π–π interactions with centroid–centroid distances of 3.5349 (12) and 3.8845 (13) Å for (II) and 3.588 (2) Å for (III). In (II) and (III), the thiophene rings are orientationally disordered over two sites, with occupancy ratios of 0.69:0.31 for (II), and 0.528 (4):0.472 (4) and 0.632 (5):0.368 (5) for (III). |
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