Toyokazu Muto

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccwt81z

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Distinguishment of Weak Interactions of Hydrogen Atoms Bound to Carbon Atoms: X-Ray Crystal Structural and Hirshfeld Surface Analyses of 2- Hydroxy-7-methoxy-3-(2,4,6-trimethylbenzoyl)naphthalene with the 2- Methoxylated Homologue

Letters in Organic Chemistry (2021)

Kikuko Iida Toyokazu Muto Miyuki Kobayashi Hiroaki Iitsuka Kun Li

Abstract: X-ray crystal and Hirshfeld surface analyses of 2-hydroxy-7-methoxy-3-(2,4,6- trimethylbenzoyl)naphthalene and its 2-methoxylated homologue show quantitatively and visually distinct molecular contacts in crystals and minute differences in the weak intermolecular interactions. The title compound has a helical tubular packing, where molecules are piled in a two-folded head-to-tail fashion. The homologue has a tight zigzag molecular string lined up behind each other via nonclassical intermolecular hydrogen bonds between the carbonyl oxygen atom and the hydrogen atom of the naphthalene ring. The dnorm index obtained from the Hirshfeld surface analysis quantitatively demonstrates stronger molecular contacts in the homologue, an ethereal compound, than in the title compound, an alcohol, which is consistent with the higher melting temperature of the former than the latter. Stabilization through the significantly weak intermolecular nonclassical hydrogen bonding interactions in the homologue surpasses the stability imparted by the intramolecular C=O…H–O classical hydrogen bonds in the title compound. The classical hydrogen bond places the six-membered ring in the concave of the title molecule. The hydroxy group opposingly disturbs the molecular aggregation of the title compound, as demonstrated by the distorted H…H interactions covering the molecular surface, owing to the rigid molecular conformation. The position of effective interactions predominate over the strength of the classical/nonclassical hydrogen bonds in the two compounds.

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Hydrogen atom

Atoms in molecules

10.2174/1570178619666211231105233

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CCDC 799551: Experimental Crystal Structure Determination

The Cambridge Structural Database (2010)

Toyokazu Muto Yu Kato A. Nagasawa Akiko Okamoto Noriyuki Yonezawa

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccvtzzl

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CCDC 872633: Experimental Crystal Structure Determination

The Cambridge Structural Database (2012)

Toyokazu Muto Kosuke Sasagawa Akiko Okamoto H. Oike Noriyuki Yonezawa

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccy91gq

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CCDC 605352: Experimental Crystal Structure Determination

The Cambridge Structural Database (2006)

Katel Hervé-Aubert Olivier Cador S. Golhen Karine Costuas Jean‐François Halet

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccn9xhb

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CCDC 605351: Experimental Crystal Structure Determination

The Cambridge Structural Database (2006)

Katel Hervé-Aubert Olivier Cador S. Golhen Karine Costuas Jean‐François Halet

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccn9xg9

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CCDC 850680: Experimental Crystal Structure Determination

The Cambridge Structural Database (2011)

Toyokazu Muto Kosuke Sasagawa Akiko Okamoto H. Oike Noriyuki Yonezawa

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccxk69y

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7-Methoxy-1-(4-nitrobenzoyl)naphthalen-2-yl 4-nitrobenzoate

Acta Crystallographica Section E Structure Reports Online (2011)

Toyokazu Muto Daichi Hijikata Akiko Okamoto Hideaki Oike Noriyuki Yonezawa

In the title compound, C(25)H(16)N(2)O(8), the dihedral angle between the naphthalene ring system and the benzene ring of the nitro-phenyl ketone unit is 82.64 (7)°. The bridging ester O-C(=O)-C plane makes dihedral angles of 42.12 (8) and 11.47 (9)°, respectively, with the naphthalene ring system and the benzene ring of the nitro-phenyl ester unit. In the crystal, two types of weak inter-molecular C-H⋯O inter-actions are observed.

Dihedral angle

10.1107/s1600536811027619

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(3,6-Dimethoxynaphthalen-2-yl)(phenyl)methanone

Acta Crystallographica Section E Structure Reports Online (2011)

Yuichi Kato Ryo Takeuchi Toyokazu Muto Akiko Okamoto Noriyuki Yonezawa

In the title compound, C(19)H(16)O(3), the dihedral angle between the naphthalene ring system and the phenyl ring is 68.32 (5)°. The bridging carbonyl C-C(=O)-C plane makes a dihedral angle of 54.32 (5)° with the naphthalene ring system and 21.45 (6)° with the phenyl ring. An inter-molecular C-H⋯O hydrogen bond exists between the H atom of one meth-oxy group and the O atom of the second meth-oxy group in an adjacent mol-ecule. The crystal packing is additionally stabilized by a weak C-H⋯O inter-molecular inter-action between an H atom of the naphthalene ring and the O atom of the carbonyl group.

Dihedral angle

10.1107/s1600536811005630

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[8-(4-Chlorobenzoyl)-2,7-dimethoxynaphthalen-1-yl](2,4,6-trimethylphenyl)methanone

Acta Crystallographica Section E Structure Reports Online (2012)

Toyokazu Muto Kosuke Sasagawa Akiko Okamoto Hideaki Oike Noriyuki Yonezawa

In the title compound, C(29)H(25)ClO(4), the dihedral angle between the benzene rings of the 2,4,6-trimethyl-benzoyl group and the 4-chloro-benzoyl group is 65.19 (9)°. The dihedral angles between the naphthalene ring system and the benzene rings of the 2,4,6-trimethyl-benzoyl group and the 4-chloro-benzoyl group are 85.66 (8) and 69.48 (8)°, respectively. In the crystal, two types of inter-molecular C-H⋯O inter-actions and an intra-molecular C-H⋯O inter-action are observed. Moreover, there is a short intra-molecular C=O⋯C=O contact of 2.614 (2) Å between the benzoyl substituents.

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10.1107/s1600536812008112

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