European Journal of Chemistry 2017, 8(2), 188-194 | doi: https://doi.org/10.5155/eurjchem.8.2.188-194.1572 | Get rights and content

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Crystal structure of 1-benzoyl-2,7-dimethoxy-8-(3,5-dimethylbenzoyl) naphthalene: Head-to-head fashioned molecular motif for accumulating weak non-classical hydrogen bonds


Takeshi Yokoyama (1) , Takahiro Mido (2) , Genta Takahara (3) , Kazuki Ogata (4) , Elżbieta Chwojnowska (5) , Noriyuki Yonezawa (6) , Akiko Okamoto (7,*)

(1) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 184-8588, Koganei, Tokyo, Japan
(2) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 184-8588, Koganei, Tokyo, Japan
(3) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 184-8588, Koganei, Tokyo, Japan
(4) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 184-8588, Koganei, Tokyo, Japan
(5) Faculty of Chemistry, Warsaw University of Technology, 00664, Warsaw, Poland
(6) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 184-8588, Koganei, Tokyo, Japan
(7) Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 184-8588, Koganei, Tokyo, Japan
(*) Corresponding Author

Received: 10 Apr 2017 | Revised: 08 May 2017 | Accepted: 10 May 2017 | Published: 30 Jun 2017 | Issue Date: June 2017

Abstract


Title compound, 1-benzoyl-2,7-dimethoxy-8-(3,5-dimethylbenzoyl)naphthalene, an unsymmetrically substituted aromatic diketone compound having non-coplanarly accumulated aromatic rings structure, has been synthesized and its crystal structure has been determined by X-ray crystallography. The asymmetric unit of title compound contains two independent conformers. For each conformer, the two aroyl groups are non-coplanarly situated against the naphthalene ring plane and oriented in an opposite direction. The 3,5-dimethylbenzoyl group leans more than the non-substituted benzoyl group on the other peri-position of the naphthalene ring. The characteristics in the single molecular crystal structure of this unsymmetrical compound show unique relationship with two symmetrically substituted homologues, namely 1,8-dibenzoyl-2,7-dimethoxynaphthalene and 2,7-dimethoxy-1,8-bis(3,5-dimethylbenzoyl) naphthalene. Dihedral angles between 3,5-dimethylbenzene ring and naphthalene ring of 2,7-dimethoxy-1,8-bis(3,5-dimethylbenzoyl)naphthalene are larger than those between benzene ring and naphthalene ring of 1,8-dibenzoyl-2,7-dimethoxynaphthalene. Dihedral angle between 3,5-dimethylbenzoyl group and naphthalene ring in title compound is close to those of symmetrical homologue having two 3,5-dimethylbenzoyl groups. In the similar manner, dihedral angle between non-substituted benzoyl group and naphthalene ring in title compound is also close to those of symmetrical homologue bearing two non-substituted benzoyl groups. On the other hand, the crystal packing of title compound has rather similar feature with 2,7-dimethoxy-1,8-bis(3,5-dimethylbenzoyl)naphthalene. Two compounds have common crystalline molecular structural motif of head-to-head fashioned intermolecular interaction of 3,5-dimethylbenzoyl moieties. It is interpreted that the interactions between (sp3)C–H and π orbital preferentially govern the molecular packing motif. Molecular structure feature of title compound and the symmetrically 3,5-dimethylbenzoylated homologue strongly manifests that accumulation of weak non-classical hydrogen bonds play a crucial role in determination of the crystal packing rather than sole function of stronger non-classical hydrogen bond and π…π stacking.


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Keywords


Cooperative effect; Crystal engineering; Weak hydrogen bonds; Noncovalent interactions; Head-to-head orientation; X-ray single crystal structure

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DOI: 10.5155/eurjchem.8.2.188-194.1572

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Funding information


Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 184-8588, Koganei, Tokyo, Japan

Citations

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[1]. Teresa L. Mako, Joan M. Racicot, Mindy Levine
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How to cite


Yokoyama, T.; Mido, T.; Takahara, G.; Ogata, K.; Chwojnowska, E.; Yonezawa, N.; Okamoto, A. Eur. J. Chem. 2017, 8(2), 188-194. doi:10.5155/eurjchem.8.2.188-194.1572
Yokoyama, T.; Mido, T.; Takahara, G.; Ogata, K.; Chwojnowska, E.; Yonezawa, N.; Okamoto, A. Crystal structure of 1-benzoyl-2,7-dimethoxy-8-(3,5-dimethylbenzoyl) naphthalene: Head-to-head fashioned molecular motif for accumulating weak non-classical hydrogen bonds. Eur. J. Chem. 2017, 8(2), 188-194. doi:10.5155/eurjchem.8.2.188-194.1572
Yokoyama, T., Mido, T., Takahara, G., Ogata, K., Chwojnowska, E., Yonezawa, N., & Okamoto, A. (2017). Crystal structure of 1-benzoyl-2,7-dimethoxy-8-(3,5-dimethylbenzoyl) naphthalene: Head-to-head fashioned molecular motif for accumulating weak non-classical hydrogen bonds. European Journal of Chemistry, 8(2), 188-194. doi:10.5155/eurjchem.8.2.188-194.1572
Yokoyama, Takeshi, Takahiro Mido, Genta Takahara, Kazuki Ogata, Elżbieta Chwojnowska, Noriyuki Yonezawa, & Akiko Okamoto. "Crystal structure of 1-benzoyl-2,7-dimethoxy-8-(3,5-dimethylbenzoyl) naphthalene: Head-to-head fashioned molecular motif for accumulating weak non-classical hydrogen bonds." European Journal of Chemistry [Online], 8.2 (2017): 188-194. Web. 3 Jun. 2023
Yokoyama, Takeshi, Mido, Takahiro, Takahara, Genta, Ogata, Kazuki, Chwojnowska, Elżbieta, Yonezawa, Noriyuki, AND Okamoto, Akiko. "Crystal structure of 1-benzoyl-2,7-dimethoxy-8-(3,5-dimethylbenzoyl) naphthalene: Head-to-head fashioned molecular motif for accumulating weak non-classical hydrogen bonds" European Journal of Chemistry [Online], Volume 8 Number 2 (30 June 2017)

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