Abstract

In the title compound, C26H20O5, a 1,2-di-hydro-naphthalene derivative, the cyclo-hexa-1,3-diene ring of the 1,2-di-hydro-naphthalene ring system adopts a half-chair conformation. The mean plane of the 1,2-di-hydro-napthalene ring system makes dihedral angles of 86.23 (6) and 64.80 (7)° with two phenyl rings. The carbonyl O atom attached to the di-hydro-naphthalene ring system deviates from the mean plane of the 1,2-di-hydro-naphthalene ring system by 0.618 (1) Å. In the crystal, the mol-ecules are linked into layers parallel to the bc plane via two kinds of C-H⋯O inter-actions, one of which forms a C(10) chain motif running along the c-axis direction and the other forms an R22(6) ring motif. Adjacent layers are further connected by C-H⋯π and offset π-π inter-actions [centroid-centroid distance = 3.6318 (9) Å].

Highlights

  • In the title compound, C26H20O5, a 1,2-dihydronaphthalene derivative, the cyclohexa-1,3-diene ring of the 1,2-dihydronaphthalene ring system adopts a half-chair conformation

  • The molecules are linked into layers parallel to the bc plane via two kinds of C—HÁ Á ÁO interactions, one of which forms a C(10) chain motif running along the c-axis direction and the other forms an R22(6) ring motif

  • The C11–C16 phenyl ring is almost perpendicular to the 1,2-dihydronaphthalene C1–C10 ring system with a dihedral angle of 83.83 (7)

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Summary

Chemical context

Naphthalene derivatives have manifested applications in many fields, for example, as colorants, explosives, disinfectants, insecticides and the plant hormone auxin. Naphthalene derivatives have been identified as a new range of potent anti-microbials that are effective against a wide range of human pathogens and have diverse and interesting antibiotic properties with minimum toxicity (Rokade & Sayyed, 2009; Upadhayaya et al, 2010). Compounds with noncoplanarly accumulated aromatic rings have received attention from organic chemists and materials chemists as unique structural building blocks, because they provide characteristic optical and electronic properties originating from their structural features. Biphenyl and binaphthyl are applied to optically active molecular catalysts and polymer materials on the basis of their axial chiralities (Deria et al, 2013). The structures of similar 1-oxo-1,2-dihydronaphtalene derivatives, namely, dimethyl 4-(4-methoxyphenyl)-2-(4methylphenyl)-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-2phenyl-2,4-bis(thiophen-2-yl)-1,2-dihydronaphthalene-3carboxylate, have been reported by Gopinath et al (2017)

Structural commentary
Supramolecular features
Synthesis and crystallization
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