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Low-melting molecular complexes: Part VII. 2,3-, 2,5- and 3,4-hexanediones and their molecular complexes with chloroform

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Abstract

Crystals of three isomeric 2,3-, 2,5- and 3,4-hexanediones 1–3 and of molecular complexes (1:2) of 2 and 3 with chloroform (4 and 5) were grown by in situ cryocrystallisation and characterised by single-crystal X-ray crystallography. The intermolecular interactions and packing motifs were examined using the analysis of pairwise energies of intermolecular interactions. The method has revealed the importance of carbonyl…carbonyl interactions in the structures 1, 3 and 4 and the relatively weaker halogen bonds in the structures 4 and 5.

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References

  1. Steiner T (2002) Angew Chem Int Ed 41:48–76

    Article  CAS  Google Scholar 

  2. Desiraju GR (2010) Angew Chem Int Ed 50:52–59

    Article  Google Scholar 

  3. Dunitz JD (2015) IUCrJ 2:157–158

    Article  CAS  Google Scholar 

  4. Thakur TS, Dubey R, Desiraju GR (2015) IUCrJ 2:159–160

    Article  CAS  Google Scholar 

  5. Lecomte C, Espinosa E, Matta CF (2015) IUCrJ 2:161–163

    Article  CAS  Google Scholar 

  6. McKinnon JJ, Spackman MA, Mitchell AS (2004) Acta Cryst B60:627–668

    Article  CAS  Google Scholar 

  7. Bui TTT, Dahaoui S, Lecomte C, Desiraju GR, Espinosa E (2009) Angew Chem Int Ed 48:3838–3841

    Article  CAS  Google Scholar 

  8. Zorky PM, Obodovskaya AE, Panina NG (2003) Crystallogr Rep 48(4):536–541

    Article  CAS  Google Scholar 

  9. Dunitz JD, Gavezzotti A (2012) Cryst Growth Des 12:5873–5877

    Article  CAS  Google Scholar 

  10. Shishkin OV (2008) Chem Phys Lett 458:96–100

    Article  CAS  Google Scholar 

  11. Schollmeyer D, Shishkin OV, Rühl T, Vysotsky MO (2008) CrystEngComm 10:715–723

    Article  CAS  Google Scholar 

  12. Merz K, Evers MV, Uhl F, Zubatyuk RI, Shishkin OV (2014) Cryst Growth Des 14:3124–3130

    Article  CAS  Google Scholar 

  13. Zubatyuk RI, Sinelshchikova AA, Enakieva YY, Gorbunova YG, Tsivadze AY, Nefedov SE, Bessmertnykh-Lemeune A, Guilard R, Shishkin OV (2014) CrystEngComm 16:10428–10438

    Article  CAS  Google Scholar 

  14. Shishkin OV, Zubatyuk RI, Shishkina SV, Dyakonenko VV, Medviediev VV (2014) Phys Chem Chem Phys 16:6773–6786

    Article  CAS  Google Scholar 

  15. Yufit DS, Shishkin OV, Zubatyuk RI, Howard JAK (2014) Cryst Growth Des 14:4303–4309

    Article  CAS  Google Scholar 

  16. Yufit DS, Shishkin OV, Zubatyuk RI, Howard JAK (2014) Z Kristallogr 229(9):647–649

    Google Scholar 

  17. Yufit DS, Howard JAK (2005) J Appl Cryst 38:583–586

    Article  CAS  Google Scholar 

  18. Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H (2009) J Appl Cryst 42:339–341

    Article  CAS  Google Scholar 

  19. Sheldrick GM (2008) Acta Cryst A64:112–122

    Article  Google Scholar 

  20. Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA (2008) J Appl Cryst 41:466–470

    Article  CAS  Google Scholar 

  21. Allen FH, Bruno IJ (2010) Acta Cryst B66:380–386

    Article  Google Scholar 

  22. Møller C, Plesset MS (1934) Phys Rev 46:618–622

    Article  Google Scholar 

  23. McLean AD, Chandler GS (1980) J Chem Phys 72:5639–5648

    Article  CAS  Google Scholar 

  24. Raghavachari K, Binkley JS, Seeger R, Pople JA (1980) J Chem Phys 72:650–654

    Article  Google Scholar 

  25. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone, V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ: Gaussian 09, Revision A.2. Wallingford CT: Gaussian, Inc; 2009

  26. Zai D-X (2012) Acta Cryst E68:o3245

    Google Scholar 

  27. Ducourant B, Maury C, Lere-Porte J-P, Petrissans J, Ribet J-L (1986) Acta Cryst C42:341–343

    CAS  Google Scholar 

  28. Allen FH, Baalham CA, Lommerse JPM, Raithby PR (1998) Acta Cryst B54:320–329

    Article  CAS  Google Scholar 

  29. Yufit DS, Howard JAK (2012) CrystEngComm 14:2003–2008

    Article  CAS  Google Scholar 

  30. Yufit DS, Howard JAK (2010) CrystEngComm 12:737–741

    Article  CAS  Google Scholar 

  31. Shishkin OV, Zubatyuk RI, Shishkina SV, Dyakonenko VV, Medviediev VV (2014) Phys Chem Chem Phys 16:6773–6786

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Durham University, South Rd., Durham, DH1 3LE, UK

    D. S. Yufit & M. A. Fox

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  1. D. S. Yufit
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  2. M. A. Fox
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Correspondence to D. S. Yufit.

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Dedicated to the memory of Prof. O. V. Shishkin, a colleague and a friend.

Part VI see Ref. [15].

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Yufit, D.S., Fox, M.A. Low-melting molecular complexes: Part VII. 2,3-, 2,5- and 3,4-hexanediones and their molecular complexes with chloroform. Struct Chem 27, 9–15 (2016). https://doi.org/10.1007/s11224-015-0620-x

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  • DOI: https://doi.org/10.1007/s11224-015-0620-x

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