European Journal of Chemistry

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



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Takeshi Yokoyama
Takahiro Mido
Genta Takahara
Kazuki Ogata
Elżbieta Chwojnowska
Noriyuki Yonezawa
Akiko Okamoto

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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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, 188-194.

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References

[1]. Pauling, L. The Nature of the Chemical Bond and the Structure of Molecules and Crystals. An Introduction to Modern Structural Chemistry, 2nd edn, Oxford University Press, London, 1940.

[2]. Atkins, P. General Chemistry, Scientific American Books, New York, 1989.

[3]. Desiraju, G. R. J. Mol. Struct. 2003, 656, 5-15.
https://doi.org/10.1016/S0022-2860(03)00354-5

[4]. Desiraju, G. R. Cryst. Growth Des. 2011, 11, 896-898.
https://doi.org/10.1021/cg200100m

[5]. Aakeroy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407.
https://doi.org/10.1039/CS9932200397

[6]. Desiraju, G. R. Crystal Engineering. The Design of Organic Solids, Elsevier, Amsterdam, 1989.

[7]. Desiraju, G. R. Angew. Chem. Int. Ed. 1995, 34(21), 2311-2327.
https://doi.org/10.1002/anie.199523111

[8]. Hisaki, I.; Nakagawa, S.; Ikenaka, N.; Imamura, Y.; Katouda, M.; Tashiro, M.; Tsuchida, H.; Ogishi, T.; Sato, H.; Tohnai, N.; Miyata, M. J. Am. Chem. Soc. 2016, 138 (20), 6617-6628.
https://doi.org/10.1021/jacs.6b02968

[9]. Sasaki, T.; Ida, Y.; Hisaki, I.; Tsuzuki, S.; Tohnai, N.; Coquerel, G.; Sato, H.; Miyata, M. Crystal Growth Design 2016, 16(3), 1626-1635.
https://doi.org/10.1021/acs.cgd.5b01724

[10]. Etter, M. C. Acc. Chem. Res. 1990, 23, 120‐126.
https://doi.org/10.1021/ar00172a005

[11]. Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511-544.
https://doi.org/10.1146/annurev.physchem.48.1.511

[12]. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112(14), 5525-5534.
https://doi.org/10.1021/ja00170a016

[13]. Jones, P. G.; Vancea, F. Cryst. Eng. Comm. 2003, 5, 303-304.
https://doi.org/10.1039/B309038H

[14]. Khavasi, H. R.; Salimi, A. R.; Eshtiagh-Hosseini, H.; Amini, M. M. Cryst. Eng. Comm. 2011, 13, 3710-3717.
https://doi.org/10.1039/c0ce00981d

[15]. Dhinakaran, M. K.; Soundarajan, K.; Das, T. M. New J. Chem. 2014, 38, 4371–4379.
https://doi.org/10.1039/C4NJ00415A

[16]. Kong, Y. B.; Zhu, J. Y.; Chen, Z. W.; Liu, L. X. Canadian J. Chem. 2014, 92(4), 269-273.
https://doi.org/10.1139/cjc-2013-0435

[17]. Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296.
https://doi.org/10.1021/ar00010a002

[18]. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond, In Structural Chemistry and Biology, Oxford University Press Inc., New York, 2001.
https://doi.org/10.1093/acprof:oso/9780198509707.001.0001

[19]. Surov, A. O.; Manin, A. N.; Voronin, A. P.; Churakov, A. V.; Perlovich, G. L.; Vener, M. V. Crystal Growth Design 2017, 17(3), 1425-1437.
https://doi.org/10.1021/acs.cgd.7b00019

[20]. Okamoto, A.; Yonezawa, N. J. Synth. Org. Chem. Jpn. 2015, 73(4), 339-360.
https://doi.org/10.5059/yukigoseikyokaishi.73.339

[21]. Okamoto, A.; Muto, T.; Siqingaowa; Takahara, G.; Yonezawa, N. Eur. J. Chem. 2017, 8(1), 33‐41.
https://doi.org/10.5155/eurjchem.8.1.33-41.1529

[22]. Ogata, K.; Nagasawa, A.; Yonezawa, N.; Okamoto, A. Eur. J. Chem. 2017, 8(1), 20-24.
https://doi.org/10.5155/eurjchem.8.1.20-24.1530

[23]. Takahara, G.; Sakamoto, R.; Ogata, K.; Ohisa, S.; Mido,T.; Yokoyama,T.; Yonezawa, N.; Okamoto, A. Eur. Chem. Bull. 2017, 6(1), 31–37.

[24]. Siqingaowa; Tsumuki, T.; Ogata, K.; Yonezawa, N.; Okamoto, A. Acta Cryst. E 2016, 72, 1819-1823.
https://doi.org/10.1107/S2056989016018077

[25]. Okamoto, A.; Watanabe, S.; Nakaema, K.; Yonezawa, N. Cryst. Str. Theo. Appl. 2012, 1,121-127.

[26]. Muto, T.; Sasagawa, K.; Okamoto, A.; Oike, H.; Yonezawa. N. Acta Cryst. E 2012, 68, o1200-o1200.
https://doi.org/10.1107/S1600536812012202

[27]. Armarego, W.L. F.; Perrin, D. D. Purification of Laboratory Chemicals, Fourth edition, Reed Educational and Professional Publishing Ltd, Oxford, 1996, pp. 9-206.

[28]. Kato, Y.; Nagasawa, A.; Hijikata, D.; Okamoto, A.; Yonezawa, N. Acta Cryst. E 2010, 66, o2659-o2659.
https://doi.org/10.1107/S1600536810038195

[29]. Rigaku (1998). PROCESS‐AUTO. Rigaku Corporation, Tokyo, Japan.

[30]. Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.

[31]. Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Siliqi, D.; Spagna, R. J. Appl. Cryst. 2007, 40, 609‐613.
https://doi.org/10.1107/S0021889807010941

[32]. Sheldrick, G. M. Acta Cryst. A 2008, 64, 112‐122.
https://doi.org/10.1107/S0108767307043930

[33]. Burnett, M. N.; Johnson, C. K. (1996). ORTEPIII. Report ORNL‐ 6895. Oak Ridge National Laboratory, Tennessee, USA.

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