Synthon modularity in cocrystals of 4-bromobenzamide with n-alkanedicarboxylic acids: Type i and type II halogen⋯halogen interactions

Crystal Growth and Design

Volumn 13, Issue 7, 2013, Pages 3242-3254

  Tothadi, Srinu ^a   Joseph, Sumy ^a   Desiraju, Gautam R ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

4-BROMOBENZAMIDE; CAMBRIDGE STRUCTURAL DATABASE ANALYSIS; CLASSIFICATION CRITERION; CO-CRYSTALS; DESIGN STRATEGIES; DICARBOXYLIC ACID; ISOSTRUCTURALITY; ORGANIC CRYSTAL;

AMIDES; CRYSTAL STRUCTURE;

IODINE;

EID: 84879878857     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg400735f     Document Type: Article

References (67)

1. Desiraju, G. R. Angew. Chem., Int. Ed. 1995, 34, 2311-2327
2. Tothadi, S.; Desiraju, G. R. Cryst. Growth Des. 2012, 12, 6188-6198
3. Almarsson, Ö.; Zaworotko, M. J. Chem. Commun. (Cambridge, U.K.) 2004, 1889-1896
4. Vishweshwar, P.; McMahon, J. A.; Peterson, M. L.; Hickey, M. B.; Shattock, T. R.; Zaworotko, M. J. Chem. Commun. (Cambridge, U.K.) 2005, 4601-4603
5. Seaton, C. C.; Parkin, A. Cryst. Growth Des. 2011, 11, 1502-1511
6. Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. Angew. Chem., Int. Ed. 2001, 40, 3240-3242
7. Tothadi, S.; Mukherjee, A.; Desiraju, G. R. Chem. Commun. (Cambridge, U.K.) 2011, 47, 12080-12082
8. In Making Crystals by Design: From Molecules to Molecular Materials, Methods, Techniques, Applications; Grepioni, F.; Braga, D., Eds.; Wiley-VCH: Weinheim, Germany, 2007; pp 209-240.
9. Dey, A.; Jetti, R. K. R.; Boese, R.; Desiraju, G. R. CrystEngComm 2003, 5, 248-252
10. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989, pp 175-198.
11. Desiraju, G. R.; Vittal, J. J.; Ramanan, A. Crystal Engineering: A Textbook; World Scientific: Singapore, 2011.
12. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386-395
13. Saha, B. K.; Nangia, A.; Jaskólski, M. CrystEngComm 2005, 7, 355-358
14. Espallargas, G. M.; Brammer, L.; Sherwood, P. Angew. Chem., Int. Ed. 2006, 45, 435-440
15. Reddy, C. M; Kirchner, M. T; Gundakaram, R. C; Padmanabhan, K. A; Desiraju, G. R. Chem.-Eur. J. 2006, 12, 2222-2234
16. Aakeröy, C. B.; Fasulo, M.; Schultheiss, N.; Desper, J.; Moore, C. J. Am. Chem. Soc. 2007, 129, 13772-13773
17. Aakeröy, C. B.; Desper, J.; Helfrich, B. A.; Metrangolo, P.; Pilati, T.; Resnati, G.; Stevenazzib, A. Chem. Commun. (Cambridge, U.K.) 2007, 4236-4238
18. Raatikainen, K.; Rissanen, K. Chem. Sci. 2012, 3, 1235-1239
19. Desiraju, G. R. Angew. Chem., Int. Ed. 2007, 46, 8342-8356
20. Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem., Int. Ed. 2008, 47, 6114-6127
21. Legon, A. C. Phys. Chem. Chem. Phys. 2010, 12, 7736-7747
22. Politzer, P.; Murray, J. S; Clark, T. Phys. Chem. Chem. Phys. 2010, 12, 7748-7757
23. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76
24. Desiraju, G. R. Angew. Chem., Int. Ed. 2010, 49, 2-10
25. Politzer, P.; Murray, J. S; Concha, M. C. J. Mol. Model. 2007, 13, 643-650
26. Chudzinski, M. G.; Taylor, M. S. J. Org. Chem. 2012, 77, 3483-3491
27. Tsuzuki, S.; Uchimaru, T.; Wakisaka, A.; Ono, A.; Sonoda, T. Phys. Chem. Chem. Phys. 2013, 15, 6088-6096
28. The Cambridge Structural Database version 5.34. ConQuest 1.15; Cambridge Crystallographic Data Centre: Cambridge, U.K., Nov 2012, Feb 2013 update.
29. RigakuMercury375R/M CCD. CrystalClear-SM Expert 2.0 rc14; Rigaku Corporation: Tokyo, Japan, 2009.
30. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
31. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838
32. Spek, A. L. Acta Crystallogr. 2009, D65, 148-155
33. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Chem. Commun. (Cambridge, U.K.) 2004, 890-891
34. Trask, A. V.; Jones, W. Top. Curr. Chem. 2005, 254, 41-70
35. Sakurai, T.; Sundaralingam, M.; Jeffrey, G. A. Acta Crystallogr. 1963, 16, 354-363
36. Ramasubbu, N.; Parthasarathy, R.; Murray-Rust, P. J. Am. Chem. Soc. 1986, 108, 4308-4314
37. Desiraju, G. R.; Parthasarathy, R. J. Am. Chem. Soc. 1989, 111, 8725-8726
38. Pedireddi, V. R.; Reddy, D. S.; Goud, B. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1994, 2353-2360
39. Bond, A. D. CrystEngComm 2007, 9, 833-834
40. Aitipamula, S.; Banerjee, R.; Bansal, A. K.; Biradha, K.; Cheney, M. L.; Choudhury, A. R.; Desiraju, G. R.; Dikundwar, A. G.; Dubey, R.; Duggirala, N.; Ghogale, P. P.; Ghosh, S.; Goswami, P. K.; Goud, N. J.; Jetti, R. K. R.; Karpinski, P.; Kaushik, P.; Kumar, D.; Kumar, V.; Moulton, B.; Mukherjee, A.; Mukherjee, G.; Myerson, A. S.; Puri, V.; Ramanan, A.; Rajamannar, T.; Reddy, C. M.; Rodriguez-Hornedo, N.; Rogers, R. D.; Guru Row, T. N.; Sanphui, P.; Shan, N.; Shete, G.; Singh, A.; Sun, C. C.; Swift, J. A.; Thaimattam, R.; Thakur, T. S.; Thaper, R. K.; Thomas, S. P.; Tothadi, S.; Vangala, V. R.; Variankaval, N.; Vishweshwar, P.; Weyna, D. R.; Zaworotko, M. J. Cryst. Growth Des. 2012, 12, 2147-2152
41. Harada, Y.; Taniguchi, T.; Takaki, Y.; Sakurai, K. Mem.Osaka Kyoiku Univ. Ser.3 1967, 16, 37
42. Nakata, K.; Ono, S.; Sakurai, K. Mem. Osaka Kyoiku Univ., Ser. 3 1979, 27, 117
43. Videnova-Adrabinska, V. Acta Crystallogr. 1996, B52, 1048-1056
44. Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. J. Am. Chem. Soc. 2002, 124, 14425-14232
45. Dey, A.; Desiraju, G. R. CrystEngComm 2004, 6, 642-646
46. Babu, N. J.; Nangia, A. Cryst. Growth Des. 2006, 6, 1753-1756
47. Haynes, D. A.; Jones, W.; Motherwell, W. D. S. CrystEngComm 2006, 8, 830-840
48. Cinčić, D.; Friščić, T.; Jones, W. Chem.-Eur. J. 2008, 14, 747-753
49. Ebenezer, S.; Muthiah, P. T.; Butcher, R. J. Cryst. Growth Des. 2011, 11, 3579-3592
50. Clarke, H. D.; Hickey, M. B.; Moulton, B.; Perman, J. A.; Peterson, M. L.; Wojtas, Ł.; Almarsson, Ö.; Zaworotko, M. J. Cryst. Growth Des. 2012, 12, 4194-4201
51. Cherukuvada, S.; Nangia, A. CrystEngComm 2012, 14, 2579-2588
52. Jones, P. G.; Hopf, H.; Silaghi, A.; Nather, C. Acta Crystallogr. 2011, C67, o405-o408
53. Vancik, H.; Simunic-Meznaric, V.; Mestrovic, E.; Halasz, I. J. Org. Chem. 2004, 69, 4829-4834
54. Halasz, I.; Mestrovic, E.; Cicak, H.; Mihalic, Z.; Vancik, H. J. Org. Chem. 2005, 70, 8461-8467
55. Gonnade, R. G.; Bhadbhade, M. M.; Shashidhar, M. S.; Sanki, A. K. Chem. Commun. (Cambridge, U.K.) 2005, 5870-5872
56. Will, S.; Rahbar, A.; Schmickler, H.; Lex, J.; Vogel, E. Angew. Chem., Int. Ed. 1990, 29, 1390-1393
57. Aritome, I.; Shimakoshi, H.; Hisaeda, Y. Acta Crystallogr. 2002, C58, o563-o408
58. Shimakoshi, H.; Baba, T.; Iseki, Y.; Aritome, I.; Endo, A.; Adachi, C.; Hisaeda, Y. Chem. Commun. (Cambridge, U.K.) 2008, 2882-2884
59. Newkome, G. R.; Arai, S.; Fronczek, F. R.; Moorefield, C. N.; Lin, X.; Weis, C. D. J. Org. Chem. 1993, 58, 898-903
60. Zvonkova, Z. V.; Gluskova, V. P. Kristallografiya 1958, 3, 559
61. Shimpi, M. R.; SeethaLekshmi, N.; Pedireddi, V. R. Cryst. Growth Des. 2007, 7, 1958-1963
62. Brehmer, T. H.; Weber, E.; Cano, F. H. J. Phys. Org. Chem. 2000, 13, 63-74
63. Brittain, H. G. Cryst. Growth Des. 2009, 9, 3497-3503
64. Brittain, H. G. Cryst. Growth Des. 2010, 10, 1990-2003
65. Adalder, T. K.; Sankolli, R.; Dastidar, P. Cryst. Growth Des. 2012, 12, 2533-2542
66. Mukherjee, A.; Tothadi, S.; Chakraborty, S.; Ganguly, S.; Desiraju, G. R. CrystEngComm 2013, 15, 4640-4654
67. Brittain, H. G. Cryst. Growth Des. 2009, 9, 2492-2499