Gopinath S, Narayanan P, Sethusankar K, Karunakaran Jeyachandran, Nandakumar Meganathan, Mohanakrishnan Arasambattu K
Department of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India.
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
Acta Crystallogr E Crystallogr Commun. 2017 Jan 13;73(Pt 2):177-182. doi: 10.1107/S2056989017000469. eCollection 2017 Feb 1.
In the title 1-oxo-1,2-di-hydro-naphthalene derivatives, CHO, (I), CHOS, (II), and CHOS, (III), the cyclo-hexa-1,3-diene rings of the 1,2-di-hydro-naphthalene ring systems adopt half-chair, boat and half-chair conformations, respectively. The carbonyl O atoms attached to the di-hydro-naphthalene ring systems are each significantly deviated from the mean plane of the 1,2-di-hydro-naphthalene 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-di-hydro-naphthalene ring systems make dihedral angles of 85.83 (3), 88.19 (3) and 81.67 (8)°, respectively, with the methyl-phenyl ring in (I), the pyrene ring in (II) and the phenyl ring in (III). In (I), the mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond, generating an (6) ring motif. In the crystal of (I), mol-ecules are linked by an inter-molecular C-H⋯O hydrogen bond, which generates a (8) zigzag chain running along [100]. Adjacent chains are further connected by C-H⋯π and offset π-π inter-actions [centroid-centroid distance = 3.6572 (9) Å], forming a double-chain structure. In the crystals of (II) and (III), mol-ecules are linked into chain structures by offset π-π inter-actions 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 thio-phene 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).
在标题化合物1-氧代-1,2-二氢萘衍生物CHO(I)、CHOS(II)和CHOS(III)中,1,2-二氢萘环系的环己-1,3-二烯环分别采用半椅式、船式和半椅式构象。连接到二氢萘环系上的羰基O原子均明显偏离1,2-二氢萘环系的平均平面,在(I)中为0.6162(12)Å,在(II)中为0.6016(16)Å,在(III)中为0.515(3)Å。1,2-二氢萘环系的平均平面与(I)中的甲基苯环、(II)中的芘环和(III)中的苯环分别形成85.83(3)°、88.19(3)°和81.67(8)°的二面角。在(I)中,分子结构通过分子内C-H⋯O氢键得以稳定,形成一个(6)环基序。在(I)的晶体中,分子通过分子间C-H⋯O氢键相连,形成一条沿[100]方向延伸的(8)锯齿链。相邻链通过C-H⋯π和偏移π-π相互作用[质心-质心距离 = 3.6572(9)Å]进一步连接,形成双链结构。在(II)和(III)的晶体中,分子通过偏移π-π相互作用连接成链状结构,(II)的质心-质心距离为3.5349(12)Å,(III)的质心-质心距离为3.8845(13)Å和3.588(2)Å。在(II)和(III)中,噻吩环在两个位置上取向无序,(II)的占有率为0.69:0.31,(III)的占有率为0.528(4):0.472(4)和0.632(5):0.368(5)。