Crystal structures of three 1-oxo-1,2-di-hydro-naphthalene derivatives: dimethyl 4-(4-meth-oxy-phen-yl)-2-(4-methyl-phen-yl)-1-oxo-1,2-di-hydro-naphthalene-2,3-di-carboxyl-ate, dimethyl 1-oxo-2-(pyren-4-yl)-4-(thio-phen-2-yl)-1,2-di-hydro-naphthalene-2,3-di-carboxyl-ate and ethyl 1-oxo-2-phenyl-2,4-bis-(thio-phen-2-yl)-1,2-di-hydro-naphthalene-3-carboxyl-ate

Autor: S, Gopinath, P, Narayanan, K, Sethusankar, Jeyachandran, Karunakaran, Meganathan, Nandakumar, Arasambattu K, Mohanakrishnan
Rok vydání: 2016
Předmět:
Zdroj: Acta Crystallographica Section E: Crystallographic Communications
ISSN: 2056-9890
Popis: In the title 1-oxo-1,2-di­hydro­naphthalene derivatives, the cyclo­hexa-1,3-diene rings of the 1,2-di­hydro­naphthalene ring systems adopt half-chair, boat and half-chair conformations, respectively. In the crystal of the methyl­phenyl compound, the mol­ecules are linked via C—H⋯O, C—H⋯π and π–π inter­actions, forming a double-chain structure, while in the crystals of the other two compounds, mol­ecules are linked by π–π inter­actions, forming a chain structure.
In the title 1-oxo-1,2-di­hydro­naphthalene derivatives, C28H24O6, (I), C34H22O5S, (II), and C27H20O3S2, (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).
Databáze: OpenAIRE