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Crystallographic and theoretical studies of 4,4′-dimethyl-7,7′-bi([1,2,5]thiadiazolo[3,4-b]pyridylidene)–chloranilic acid (1/1) with intermolecular O–H···N hydrogen bonds and S···O heteroatom interactions

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Abstract

The molecular and crystal structure of a 1:1 co-crystal of 4,4′-dimethyl-7,7′-bi([1,2,5]thiadiazolo[3,4-b]pyridylidene)–chloranilic acid, (1), has been determined by X-ray diffraction at the monoclinic space group P21/c with cell parameters of a = 8.422(6), b = 7.343(4), c = 16.112(7) Å, β = 104.988(8)°, V = 962.5(10) Å3 and Z = 2. In the crystal structure, two components connect via the intermolecular O–H···N hydrogen bonds [2.804(4) Å] and S···O heteroatom interaction [2.945(3) Å] with R 2 2(7) couplings to form a unique and infinite one-dimensional supramolecular tape structure. The calculations of (1) at the HF/6-31G(d), MP2/6-31G(d), and B3LYP/6-31G(d) levels can almost reproduce X-ray geometry. In addition, the distances of the intermolecular O–H···N and S···O interactions by MP2/6-31G(d) and B3LYP/6-31G(d) levels agree well with those in the crystal. The calculated binding energies corrected BSSE and ZPE are −4.487 (HF), −7.473 (MP2), and −5.640 (B3LYP) kcal/mol. The results suggest that the complex (1) is very stable and the dispersion interaction is significantly important for the attractive intermolecular interaction in (1). The NBO analysis has revealed that the n(N) → σ*(O–H) interaction gives the strongest stabilization to the system and the major interaction for the intermolecular S···O contact is n(O) → σ*(S–N).

Index Abstract

In the crystal structure of the title compound, the molecules are linked by intermolecular O–H···N hydrogen bonds and short S···O heteroatom interactions with R 2 2(7) couplings to construct a unique and infinite one-dimensional supramolecular tape structure.

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Acknowledgments

The authors thank the Instrument Center, Institute for Molecular Science, Okazaki, Japan, for the X-ray crystallographic analysis and Research Center for Computational Science, Okazaki Research Facilities, National Institutes of Natural Sciences, Okazaki, Japan, for the computations.

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Authors and Affiliations

  1. Institute for Molecular Science, Myodaiji, Okazaki, 444-8585, Japan

    Masaaki Tomura

  2. Department of Materials Science and Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan

    Katsuhiko Ono

  3. Department of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, Nagatsuta, Midori-ku, Yokohama, 226-8502, Japan

    Yoshiro Yamashita

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  1. Masaaki Tomura
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  2. Katsuhiko Ono
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  3. Yoshiro Yamashita
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Correspondence to Masaaki Tomura.

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Tomura, M., Ono, K. & Yamashita, Y. Crystallographic and theoretical studies of 4,4′-dimethyl-7,7′-bi([1,2,5]thiadiazolo[3,4-b]pyridylidene)–chloranilic acid (1/1) with intermolecular O–H···N hydrogen bonds and S···O heteroatom interactions. Struct Chem 19, 967–974 (2008). https://doi.org/10.1007/s11224-008-9382-z

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