Crystal Growth & Design
C2H4Br2@PzC were obtained for this study. X-ray analysis of
Page 8 of 10
8. Centers for Disease Control and Prevention. Fourth report on
1
2
3
4
5
6
7
8
the obtained crystals was challenging as the crystals were
unstable at room temperature and deteriorates within seconds
when taken out from the mother liquor due to porous nature.
Also, it is a well-documented fact that it is difficult to obtain
high quality crystallographic data of supramolecular
assemblies when the molecular weight reaches 2,000 g/mol.34-
36 The crystals mentioned above are in the range 1800 to 3000
g/mol due to which a good quality data set was hard to obtain.
human exposure to environmental chemical (U.S. Department of
Health and Human Services, Centers for Disease Control and
Prevention, Atlanta, GA, 2009).
9. Pang, X.; Jin, W. J. Exploring the Halogen Bond Specific
Solvent Effects in Halogenated Solvent Systems by ESR Probe.
New J. Chem. 2015, 39, 5477-5483.
10. El-Sheshtawy, H. S.; Bassil, B. S.; Assaf, K. I.; Kortz, U.; Nau,
W. M. Halogen Bonding inside a Molecular Container. J. Am.
Chem. Soc. 2012, 134, 19935-19941.
9
11. Sarwar, M. G.; Ajami, D.; Theodorakopoulos, G.; Petsalakis, I.
D.; Rebek, J., Jr. Amplified Halogen Bonding in a Small Space.
J. Am. Chem. Soc. 2013, 135, 13672-13675.
ASSOCIATED CONTENT
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Supporting Information.
The Supporting Information is available free of charge on the
at DOI:
X-ray crystallographic data (CCDC 1822749-1822755) (CIFs)
Materials and methods, X-ray structural studies, ESI-MS spectra,
IR spectra, TGA, NMR spectra, and additional Figures, (PDF).
12. Yang, D.; Zhao, J.; Zhao, Y.; Lei, Y.; Cao, L.; Yang, X. J.; Davi,
M.; de Sousa Amadeu, N.; Janiak, C.; Zhang, Z.; Wang, Y. Y.;
Wu, B. Encapsulation of Halocarbons in a Tetrahedral Anion
Cage. Angew. Chem., Int. Ed. 2015, 54, 8658-8661.
13. Chen, T.-H.; Popov, I.; Kaveevivitchai, W.; Chuang, Y.-C.;
Chen, Y.-S.; Jacobson, A. J.; Miljanić, O. Š. Mesoporous
Fluorinated Metal–Organic Frameworks with Exceptional
Adsorption of Fluorocarbons and CFCs. Angew. Chem., Int. Ed.
2015, 54, 13902-13906.
AUTHOR INFORMATION
Corresponding Author
14. Chen, T.-H.; Popov, I.; Kaveevivitchai, W.; Chuang, Y.-C.;
Chen, Y.-S.; Daugulis, O.; Jacobson, A. J.; Miljanić, O. Š.
Thermally robust and porous noncovalent organic framework
with high affinity for fluorocarbons and CFCs. Nat. Commun.
2014, 5, 5131.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENT
15. Sarkar, B.; Mukhopadhyay, P.; Bharadwaj, P. K. Laterally non-
symmetric aza-cryptands: synthesis, catalysis and derivatization
to new receptors. Coord. Chem. Rev. 2003, 236, 1-238.
We gratefully acknowledge financial support from the DST and
MNRE, New Delhi, India (to P.K.B.), and the SRF from IIT
Kanpur, India (to A.V.), and financial support in the form of a
postdoc fellowship from SERB (DST) (YSS/2015/001088) to
K.T.
16. Lakshminarayanan, P. S.; Kumar, D. K.; Ghosh, P. J. Am. Chem.
Soc. 2006, 128, 9600-9601.
17. Francesconi, O.; Ienco, A.; Moneti, G.; Nativi, C.; Roelens, S. A
self-assembled pyrrolic cage receptor specifically recognizes
beta-glucopyranosides. Angew. Chem., Int. Ed. 2006, 45, 6693-
6696.
REFERENCES
1. Aakeroey, C. B.; Wijethunga, T. K.; Desper, J.; Dakovic, M.
Crystal Engineering with Iodoethynylnitrobenzenes: A Group of
Highly Effective Halogen-Bond Donors. Cryst. Growth Des.
2015, 15, 3853–3861.
18. Jin, Y.; Voss, B. A.; Jin, A.; Long, H.; Noble, R. D.; Zhang, W.
Highly CO2-Selective Organic Molecular Cages: What
Determines the CO2 Selectivity. J. Am. Chem. Soc. 2011, 133,
6650-6658.
2. Priimagi, A.; Cavallo, G.; Metrangolo, P.; Resnati, G. The
Halogen Bond in the Design of Functional Supramolecular
Materials: Recent Advances. Acc. Chem. Res. 2013, 46, 2686-
2695.
19. Xu, D.; Warmuth, R. Edge-Directed Dynamic Covalent
Synthesis of a Chiral Nanocube. J. Am. Chem. Soc. 2008, 130,
7520-7521.
20. Alajarin, M.; Leonardo, C. L.; Vidal, A.; Berna, J.; Steed, J. W.
Helical Sense Bias Induced by Point Chirality in Cage
Compounds. Angew. Chem., Int. Ed. 2002, 41, 1205– 1208.
3. Hardegger, L. A.; Kuhn, B.; Spinnler, B.; Anselm, L.; Ecabert,
R.; Stihle, M.; Gsell, B.; Thoma, R.; Diez, J.; Benz, J.; Plancher,
J.-M.; Hartmann, G.; Banner, D. W.; Haap, W.; Diederich, F.
Systematic Investigation of Halogen Bonding in Protein–Ligand
Interactions. Angew. Chem., Int. Ed. 2011, 50, 314-318.
21. Imai, Y. N.; Inoue, Y.; Nakanishi, I.; Kitaura, K. Cl–π
interactions in protein–ligand complexes. Protein Sci. 2008, 17,
1129-1137.
4. Aakeröy, C. B.; Fasulo, M.; Schultheiss, N.; Desper, J.; Moore,
C. Structural Competition between Hydrogen Bonds and
Halogen Bonds. J. Am. Chem. Soc. 2007, 129, 13772-13773.
22. Chebbi, M.; Arfaoui, Y. Reactivity of pyrazole derivatives with
halomethanes: A DFT theoretical study. J. Mol. Model, 2018,
24, 198-208.
5. Desiraju, G. R.; Ho, P. S.; Kloo, L.; Legon, A. C.; Marquardt,
R.; Metrangolo, P.; Politzer, P.; Resnati, G.; Rissanen, K.
Definition of the halogen bond. Pure Appl. Chem. 2013, 85,
1711-1713.
23. Ivanov, D. M.; Kinzhalov, M. A.; Novikov, A. S.; Ananyev, I.
V.; Romanova, A. A.; Boyarskiy, V. P.; Haukka, M.;
Kukushkin, V. Y. H2C(X)−X···X− (X = Cl, Br) Halogen
Bonding of Dihalomethanes, Cryst. Growth Des. 2017, 17,
1353−1362.
6. Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. An
overview of halogen bonding. J. Mol. Model. 2007, 13, 305-311.
24. Corradi, E.; Meille, S. V.; Messina, M. T.; Metrangolo, P.;
Resnati, G. Halogen Bonding versus Hydrogen Bonding in
Driving Self-Assembly Processes Perfluorocarbon-hydrocarbon
self-assembly, part IX. Angew. Chem., Int. Ed. 2000, 39, 1782-
1786.
7. Barrie, L. A.; Bottenheim, J. W.; Schnell, R. C.; Crutzen, P. J.;
Rasmussen, R. A. Ozone destruction and photochemical
reactions at polar sunrise in the lower Arctic atmosphere. Nature
1988, 334, 138-141.
7
ACS Paragon Plus Environment