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Anchor Effect on Pedal Motion Observed in Crystal Phase of an Azobenzene Derivative

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Abstract

Some molecules having a molecular skeleton similar to that of stilbenes and azobenzenes show orientational disorder in the crystals due to pedal motion. Heretofore, the orientational disorder through pedal motion has been observed for the compounds containing only two aromatic rings in the absence of bulky substituent groups. Here we report that the pedal motion can be detected even in the presence of a bulky substituent group to which orientational disorder becomes invisible as a result of anchor effect arising from phenoxyphtalonitrile group. X-ray crystallographic analysis of the compound, C23H18N4O, reveals the existence of partially overlapped two pedal conformers. The compound crystallizes in the monoclinic space group P21/c with a = 12.9429(11) Å, b = 8.5075(5) Å, c = 21.063(2) Å and β = 123.155(6)°. Major pedal conformer is stabilized by weak C–H···O type hydrogen bond and C–H···π type edge-to-face interactions in solid state. Quantum chemical calculations at B3LYP/6-311G+(d,p) level suggest that the stabilization of the compound decreases with increasing deviation from the planar geometry of trans-azobenzene fragment.

Index Abstract

Molecular and crystal structure of 4-[2-Methyl-4-(4-ethylphenyldiazenyl)]phenoxyphtalonitrile, C23H18N4O, indicate the existence of partially overlapped two pedal conformers in which orientational disorder becomes invisible as a result of anchor effect arising from phenoxyphtalonitrile group.

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Acknowledgments

The authors wish to acknowledge Ondokuz Mayıs University for the use of the STOE IPDS II diffractometer purchased under Grants F.279 and F.377.

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Authors and Affiliations

  1. Department of Physics, Dokuz Eylül Universitesi, Fen Fakültesi, Fizik Bölümü, Tinaztepe Kampusu, 35160, Buca, Izmir, Turkey

    Hasan Karabıyık

  2. Department of Physics, Ondokuz Mayıs University, 55139, Samsun, Turkey

    Hande Petek

  3. Department of Science Education, Ondokuz Mayıs University, 55139, Samsun, Turkey

    Nazan Ocak İskeleli

  4. Department of Science Education, Sinop University, 57010, Sinop, Turkey

    Çiğdem Albayrak

  5. Department of Chemistry, Ondokuz Mayıs University, 55139, Samsun, Turkey

    Erbil Ağar

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  1. Hasan Karabıyık
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  2. Hande Petek
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  3. Nazan Ocak İskeleli
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  4. Çiğdem Albayrak
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Correspondence to Hasan Karabıyık.

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Karabıyık, H., Petek, H., İskeleli, N.O. et al. Anchor Effect on Pedal Motion Observed in Crystal Phase of an Azobenzene Derivative. J Chem Crystallogr 41, 1642–1648 (2011). https://doi.org/10.1007/s10870-011-0152-1

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  • DOI: https://doi.org/10.1007/s10870-011-0152-1

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