Stereoelectronic effects of substituent groups in the solid state. Crystal chemistry of some cubanecarboxylic and phenylpropiolic acids

Crystal Growth and Design

Volumn 3, Issue 5, 2003, Pages 675-681

  Das, Dinabandhu ^a   Jetti, Ram K R ^b   Boese, Roland ^b   Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CUBANE DERIVATIVE; DIMER;

ARTICLE; CHEMICAL ANALYSIS; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; ELECTRONICS; HYDROGEN BOND; SOLID STATE; STEREOCHEMISTRY;

EID: 0141739797     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg0341252     Document Type: Article

References (74)

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17. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
18. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
19. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
20. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
21. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
22. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
23. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
24. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
25. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
26. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
27. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
28. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
29. The balance between geometrical and chemical factors is discussed in Desiraju, G. R.; Nangia, A. Acta Crystallogr., Sect. A 1998, 54, 934-944. A number of papers have alluded to shape and size factors in crystal engineering, the so-called geometrical effect. Some selected and recent papers include: Robinson, J. M. A.; Kariuki, B. M.; Harris, K. D. M.; Philp, D. J. Chem. Soc., Perkin Trans. 2 1998, 2459-2469. Weiss, H.-C.; Boese, R.; Smith, H. L.; Haley, M. M. Chem. Commun. 1997, 2403-2404. Ibragimov, B. T.; Beketov, K. M.; Weber, E.; Seidel, J.; Sumarna, O.; Makhkamov, K. K.; Köhnke, K. J. Phys. Org. Chem. 2001, 14, 697-703. Decisively chemical effects follow typically from hydrogen bonding. The number of papers that use this interaction in crystal design is too vast to list here, but the following is an abbreviated recent list: Schwiebert, K. E.; Chin, D. N.; MacDonald, J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018-4029. Melendez, R. E.; Hamilton, A. D. In Design of Organic Solids; Weber, E., Ed.; Springer: Berlin, 1998, pp 97-129. Holman, K. T.; Pivovar, A. M.; Swift, J. A.; Ward, M. D. Acc. Chem. Res. 2001, 34, 107-118. Zaworotko, M. J. Chem. Commun. 2001, 1-9; Kolotuchin, S. V.; Fenlon, E. E.; Wilson, S. R.; Loweth, C. J.; Zimmerman, S. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2654-2657. Braga, D.; Desiraju, G. R.; Miller, J. S.; Orpen, A. G.; Price, S. L. CrystEngComm 2002, 4, 500-509. Martz, J.; Graf, E.; Cian, A. D.; Hosseini, M. W. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 177-209. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 1018-1033. Brammer, L. In Crystal Design. Structure and Function, Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Wiley: Chichester, 2003, Vol. 7, pp 1-75.
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