Paper
NJC
sp2 and sp3 carbon is not of significance in molecular crystals.
Following the analysis of C(sp2)/(sp3)–FꢀꢀꢀF–C(sp2)/(sp3) interactions
from the QTAIM approach, it was observed that these fulfill the
criteria of these being of the closed shell type for the entire FꢀꢀꢀF
bond path length and provide local stabilization (indicates the
formation of bonds) similar to the case of weak hydrogen bonds
in crystals. For future study, it would be of interest to extend this
study to donor atoms in different hybridization environments
with the F–C(sp2)/(sp3) group in different chemical environments.
Furthermore, it is also of interest to investigate the effect of
increasing fluorination on the molecule and the impact on the
stabilization energies for the different supramolecular motifs
involving organic fluorine present in the crystal.
18 T. S. Thakur, M. T. Kirchner, D. Blaser, R. Boese and
G. R. Desiraju, CrystEngComm, 2010, 12, 2079–2085.
19 K. Muller, C. Faeh and F. Diederich, Science, 2007, 317,
1881–1886.
20 D. Chopra and T. N. G. Row, CrystEngComm, 2011, 13,
2175–2186 and references therein.
21 D. Chopra, Cryst. Growth Des., 2012, 12, 541–546 and
references therein.
22 P. A. Champagne, J. Desroches and J.-F. Paquin, Synthesis,
2015, 306–322 and references therein.
23 P. Panini and D. Chopra, in Hydrogen Bonded Supramolecular
Structures, ed. Z. Li and L. Wu, Lecture Notes in Chemistry,
Springer-Verlag, Berlin, Heidelberg, 2015, vol. 87, pp. 37–67,
ISBN: 978-3-662-45755-9.
24 A. R. Choudhury and T. N. G. Row, Cryst. Growth Des., 2004,
4, 47–52.
25 A. R. Choudhury and T. N. G. Row, CrystEngComm, 2006, 8,
265–274.
26 D. Chopra, V. Thiruvenkatam, S. G. Manjunath and T. N. G.
Row, Cryst. Growth Des., 2007, 7, 868–874.
Acknowledgements
PP thanks UGC-India for research scholarship. D. C. thanks
IISER Bhopal for research facilities and infrastructure and
DST-SERB for research funding.
27 A. Schwarzer and E. Weber, Cryst. Growth Des., 2008, 8,
2862–2874.
28 V. Vasylyeva and K. Merz, Cryst. Growth Des., 2010, 10,
4250–4255.
29 V. Vasylyeva, O. V. Shishkin, A. V. Maleev and K. Merz,
Cryst. Growth Des., 2012, 12, 1032–1039.
30 M. Karanam and A. R. Choudhury, Cryst. Growth Des., 2012,
13, 4803–4814.
31 G. Kaur, P. Panini, D. Chopra and A. R. Choudhury, Cryst.
Growth Des., 2012, 12, 5096–5110.
32 G. Kaur and A. R. Choudhury, Cryst. Growth Des., 2014, 14,
1600–1616.
References
1 H.-J. Schneider, Chem. Sci., 2012, 3, 1381–1394.
2 G. K. S. Prakash, F. Wang, M. Rahm, J. Shen, C. Ni,
R. Haiges and G. A. Olah, Angew. Chem., Int. Ed., 2011, 50,
11761–11764.
3 F. F. Awwadi, R. D. Willett, K. A. Peterson and B. Twamley,
Chem. – Eur. J., 2006, 12, 8952.
4 M. Perez-Torralba, M. A. Garcia, C. Lopez, M. C. Torralba,
M. R. Torres, R. M. Claramunt and J. Elguer, Cryst. Growth
Des., 2014, 14, 3499–3509.
33 K. Merz, M. V. Evers, F. Uhl, R. I. Zubatyuk and O. V.
Shishkin, Cryst. Growth Des., 2014, 14, 3124–3130.
34 P. Panini and D. Chopra, New J. Chem., 2015, 39, 8720–8738.
35 A. Abad, C. Agullo, A. C. Cunat, C. Vilanova and M. C. R.
de Arellano, Cryst. Growth Des., 2006, 6, 46–57.
36 P. Mocilac, K. Donnelly and J. F. Gallagher, Acta Crystallogr.,
Sect. B: Struct. Sci., 2012, 68, 189–203.
37 R. Dubey, M. S. Pavan and G. R. Desiraju, Chem. Commun.,
2012, 48, 9020–9022.
38 M. Perez-Torralba, M. A. Garcia, C. Lopez, M. C. Torralba,
M. R. Torres, R. M. Claramunt and J. Elguer, Cryst. Growth
Des., 2014, 14, 3499–3509.
5 I. Saraogi, V. G. Vijay, S. Das, K. Sekar and T. N. G. Row,
Cryst. Eng., 2003, 6, 69–77.
6 M. T. Scerba, S. Bloom, N. Haselton, M. Siegler, J. Jaffe and
T. Lectka, J. Org. Chem., 2012, 77, 1605–1609.
7 X. Xu, B. Pooi, H. Hirao and S. H. Hong, Angew. Chem.,
Int. Ed., 2014, 53, 1283–1287.
8 R. Berger, G. Resnati, P. Metrangolo, E. Weber and J. Hulliger,
Chem. Soc. Rev., 2011, 40, 3496–3508 and references therein.
9 L. Shimoni and J. P. Glusker, Struct. Chem., 1994, 5,
383–397.
10 J. A. K. Howard, V. J. Hoy, D. O’Hagan and G. T. Smith,
Tetrahedron, 1996, 52, 12613–12622.
11 J. D. Dunitz and R. Taylor, Chem. – Eur. J., 1997, 3, 89–98.
39 P. Panini and D. Chopra, CrystEngComm, 2013, 15, 3711–3733.
12 V. R. Thalladi, H.-C. Weiss, D. Blaser, R. Boese, A. Nangia 40 P. Panini and D. Chopra, CrystEngComm, 2012, 14, 1972–1989.
and G. R. Desiraju, J. Am. Chem. Soc., 1998, 120, 8702–8710. 41 P. Panini and D. Chopra, Cryst. Growth Des., 2014, 14,
13 J. Parsch and J. W. Engels, J. Am. Chem. Soc., 2002, 124,
5564–5572.
14 J. D. Dunitz, ChemBioChem, 2004, 5, 614–621.
3155–3168.
42 R. F. W. Bader, Atoms in Molecules: A Quantum Theory,
Oxford University Press, Oxford, UK, 1990.
15 J. D. Dunitz and W. B. Schweizer, Chem. – Eur. J., 2006, 12, 43 (a) E. Arunan, G. R. Desiraju, R. A. Klein, J. Sadlej, S. Scheiner,
6804–6815.
I. Alkorta, D. C. Clary, R. H. Crabtree, J. J. Dannenberg,
P. Hobza, H. G. Kjaeergaard, A. C. Legon, B. Mennucci and
D. J. Nesbitt, Pure Appl. Chem., 2011, 83, 1619–1636;
(b) E. Arunan, G. R. Desiraju, R. A. Klein, J. Sadlej, S. Scheiner,
I. Alkorta, D. C. Clary, R. H. Crabtree, J. J. Dannenberg,
16 F. Cozzi, S. Bacchi, G. Filippini, T. Pilati and A. Gavezzotti,
Chem. – Eur. J., 2007, 13, 7177–7184.
17 D. Chopra and T. N. G. Row, CrystEngComm, 2008, 10,
54–67.
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