Abstract
The synthesis, crystal structures and hydrogen bonding networks of four members of the bis(pyridinecarboxamido)alkane and bis(pyridyl)alkanediamides series (1 ≤ n ≤ 8), where the amide moieties are separated by alkyl chain (-(CH2)n-) having even or odd number of -(CH2)-groups are explored and correlated with the previously reported structures. The odd members (n = odd) of both the series are found to adopt three-dimensional networks in contrast to the 1D or 2D structures of the even members (n = even). This odd-even effect on the dimensionality of the networks however disappears with increase in chain length.
The synthesis, crystal structures and hydrogen bonding networks of four members of the bis(pyridinecarboxamido)alkane and bis(pyridyl)alkanediamides series (1≤ n≤ 8), where the amide moieties are separated by alkyl chain (-(CH2)n-) having even or odd number of -(CH2)-groups are explored and the effect of chain length on the odd-even alteration of network pattern is investigated.
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References
(a) Desiraju G R and Steiner T 1999 In The weak hydrogen bond in structural chemistry and biology (Oxford: Oxford University Press); (b) Zaworotko M J 2001 Chem. Commun. p1
(a) Desiraju G R 1989 In Crystal Engineering: The design of organic solids (Amsterdam: Elsevier); (b) Desiraju G R 1995 Angew. Chem. Int. Ed. 34 2311; (c) Etter M C 1990 Acc. Chem. Res. 23 120
(a) Nguyen T L, Fowler F W and Lauher J W 2001 J. Am. Chem. Soc. 123 11057; (b) Das D and Desiraju G R 2006 Chem. Asian J. 1 231; (c) Bis J A, Vishweshwar P, Middleton R A and Zaworotko M J 2006 Cryst. Growth Des. 6 1048
(a) Sarkar M and Biradha K 2006 Cryst. Growth Des. 6 202; (b) Rajput L, Singha S and Biradha K 2007 Cryst. Growth Des. 7 2788; (c) Mukherjee G and Biradha K 2011 Cryst. Growth Des. 11 924; (d) Sarkar M and Biradha K 2005 Chem. Commun. 2229; (e) Biradha K and Rajput L 2010 In Organic crystal engineering: Frontiers in crystal engineering E R T Tiekink, J J Vittal and M J Zaworotko (Eds.) (Chichester: John Wiley Publishers)
(a) Boese R, Weiss H-C and Bläser D 1999 Angew. Chem. Int. Ed. 38 988; (b) Thalladi V R, Boese R and Weiss H-C 2000 J. Am. Chem. Soc. 122 1186; (c) Thalladi V R, Boese R and Weiss H -C 2000 Angew. Chem. Int. Ed. 39 918; (d) Thalladi V R, Nüsse M and Boese R 2000 J. Am. Chem. Soc. 122 9227
(a) Lauher J W, Chang Y L and Fowler F W 1992 Mol. Cryst. Liq. Cryst. 211 99; (b) Zhao Y L and Wu Y D 2002 J. Am. Chem. Soc. 124 2002
Batten S R and Robson R 1998 Angew. Chem. Int. Ed. 37 1460
(a) Craig D C, Dance I G and Garbutt R 1986 Angew. Chem. Int. Ed. Engl. 25 165; (b) Ermer O 1988 J. Am. Chem. Soc. 110 3747; (c) Ermer O and Eling A 1988 Angew. Chem. Int. Ed. Engl. 27 829; (d) Hoskins B F and Robson R 1990 J. Am. Chem. Soc. 112 1546; (e) Simard M, Su D and Wuest J D 1991 J. Am. Chem. Soc. 113 4696; (f) Copp S B, Subramanian S and Zaworotko M J 1992 J. Am. Chem. Soc. 114 8719; (g) Brunet P, Simard M and Wuest J D 1997 J. Am. Chem. Soc. 119 2737; (h) Reddy D S, Dewa T, Endo K and Aoyama Y 2000 Angew. Chem. Int. Ed. 39 4266; (i) Men Y B, Sun J, Huang Z- T and Zheng Q Y 2009 CrystEngComm 11 978
Sheldrick G M 1997 In Program for the Solution and Refinement of Crystal Structures, SHELX-97 (Germany: University of Gottingen)
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We gratefully acknowledge the DST for financial support and DST-FIST for single crystal diffractometer. GM thanks CSIR for a research fellowship.
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MUKHERJEE, G., BIRADHA, K. 3D, 2D and 1D networks via N-H⋯ O and N-H⋯ N hydrogen bonding by the bis-amide analogues: Effect of chain lengths and odd-even spacers. J Chem Sci 126, 1285–1290 (2014). https://doi.org/10.1007/s12039-014-0696-7
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DOI: https://doi.org/10.1007/s12039-014-0696-7