Hierarchy of Supramolecular Synthons: Persistent Carboxylic Acid···Pyridine Hydrogen Bonds in Cocrystals That also Contain a Hydroxyl Moiety

Crystal Growth and Design - Tập 8 Số 12 - Trang 4533-4545 - 2008
T.R. Shattock1, Kapildev K. Arora1, P. Vishweshwar1, Michael J. Zaworotko1
1Department of Chemistry, University of South Florida, CHE205, 4202 East Fowler Avenue, Tampa, Florida 33620

Tóm tắt

Từ khóa


Tài liệu tham khảo

Desiraju G. R., 1989, Crystal Engineering: The Design of Organic Solids

Desiraju G. R., 1995, Angew. Chem., Int. Ed., 34, 2311, 10.1002/anie.199523111

Mathias J. P., 1992, Chem. Soc. Rev., 21, 215, 10.1039/cs9922100215

Desiraju G. R., 2003, Crystal Design: Structure and Function, 10.1002/0470868015

Braga D., 2003, Chem. Commun., 2751, 10.1039/b306269b

Moulton B., 2001, Chem. Rev., 101, 1629, 10.1021/cr9900432

Etter M. C., 1982, J. Am. Chem. Soc., 104, 1095, 10.1021/ja00368a031

Dunitz J. D., 1991, Pure Appl. Chem., 63, 177, 10.1351/pac199163020177

Dunitz J. D., 1997, Chem. Eur. J., 3, 89, 10.1002/chem.19970030115

Tiekink E. R. T., 2006, Frontiers in Crystal Engineering

Pepinsky R., 1955, Phys. Rev., 100, 971

Schmidt G. M., 1971, J. Pure Appl. Chem., 27, 647, 10.1351/pac197127040647

Lehn J.-M., 1995, Supramolecular Chemistry: Concepts and Perspectives, 10.1002/3527607439

Atwood J. L., 1996, Comprehensive Supramolecular Chemistry, 6

MacNicol D. D., 1996, Comprehensive Supramolecular Chemistry, Solid-State Supramolecular Chemistry: Crystal Engineering, 6

Vögtle F., 1991, Supramolecular Chemistry

Schneider H.-J., 1991, Frontiers in Supramolecular Organic Chemistry and Photochemistry

MacDonald J. C., 1994, Chem. Rev., 94, 2383, 10.1021/cr00032a007

Atwood J. L., 1984, Inclusion compounds

Weber E., 1987, Molecular Inclusion and Molecular Recognition-Clathrates I and II: Topics in Current Chemistry, 140, 10.1007/BFb0003833

Atwood J. L., 2004, Angew. Chem., Int. Ed., 43, 2948, 10.1002/anie.200353559

Thallapally P. K., 2005, Chem. Commun., 5272, 10.1039/b511341e

Atwood J. L., 2002, Science, 296, 2367, 10.1126/science.1072252

MacGillivray L. R., 1997, J. Am. Chem. Soc., 119, 6931, 10.1021/ja970758r

Benito J. M., 2004, J. Am. Chem. Soc., 126, 10355, 10.1021/ja047864v

Iyengar S., 2005, Cryst. Growth Des., 5, 2043, 10.1021/cg050313b

Dalgarno S. J., 2006, Cryst. Growth Des., 6, 174, 10.1021/cg050261q

Zelichenok A., 1999, J. Phys. Chem. B., 103, 8702, 10.1021/jp991616h

Ishow E., 2003, J. Am. Chem. Soc., 125, 15744, 10.1021/ja038207q

Wang Y.-T., 2005, Inorg. Chem., 44, 4148, 10.1021/ic0504137

Lemaitre N., 2001, Chem. Mater., 13, 1420, 10.1021/cm001409q

Nemoto N., 1997, Chem. Mater., 9, 304, 10.1021/cm960375c

Pal T., 2003, Cryst. Growth Des., 3, 13, 10.1021/cg025583y

Gao F., 2004, J. Phys. Chem. B., 108, 3426, 10.1021/jp036330y

Huang K. S., 1997, J. Mater.Chem., 7, 713, 10.1039/a604311j

Ohi H., 2004, Inorg. Chem., 43, 4561, 10.1021/ic049468j

Anthony S. P., 2004, Cryst. Growth Des., 4, 1223, 10.1021/cg049781w

Vondrova M., 2005, Chem. Mater., 17, 4755, 10.1021/cm050830h

Park B. I., 2006, Inorg. Chem., 45, 4310, 10.1021/ic052053t

Matsumoto K., 2006, Cryst. Growth Des., 6, 1083, 10.1021/cg060073f

Uemura T., 2006, Chem. Mater., 18, 992, 10.1021/cm052427g

Fujita W., 2006, J. Am. Chem. Soc., 128, 6016, 10.1021/ja060979+

Marchal C., 2007, Inorg. Chem., 46, 6242, 10.1021/ic7009918

Neofotistou E., 2007, Inorg. Chem., 46, 8487, 10.1021/ic701414v

Moulton B., 2002, Curr. Opi. Solid State and Mater. Sci., 6, 117, 10.1016/S1359-0286(02)00047-5

McManus G. J., 2007, J. Am. Chem. Soc., 129, 9094, 10.1021/ja071271d

Biradha K., 2006, Chem. Commun., 4169, 10.1039/B606184B

Blake A. J., 1999, Coord. Chem. Rev., 183, 117, 10.1016/S0010-8545(98)00173-8

Halder G. J., 2002, Science, 298, 1762, 10.1126/science.1075948

Chui S. S. Y., 1999, Science, 283, 1148, 10.1126/science.283.5405.1148

Batten S. R., 1998, Angew. Chem., Int. Ed., 37, 1460, 10.1002/(SICI)1521-3773(19980619)37:11<1460::AID-ANIE1460>3.0.CO;2-Z

Huang J., 2003, J. Am. Chem. Soc., 125, 13334, 10.1021/ja038038+

Bandyopadhyay P., 2000, J. Am. Chem. Soc., 122, 12888, 10.1021/ja0056466

Goutenoire F., 2000, Chem. Mater., 12, 2575, 10.1021/cm991199l

Batail P., 2004, Chem. Rev., 104, 4887, 10.1021/cr040697x

Laukhina E., 2004, Chem. Mater., 16, 2471, 10.1021/cm034866q

Anthony J. E., 2001, J. Am. Chem. Soc., 123, 9482, 10.1021/ja0162459

Almarsson Ö., 2004, Chem. Commun., 1889, 10.1039/b402150a

Vishweshwar P., 2006, J. Pharm. Sci., 95, 499, 10.1002/jps.20578

Peterson M. L., 2006, J. Pharm. Pharma. Sci., 9, 317

Zaworotko M., 2004, Am. Pharm. Outsourc., 5, 16

Vishweshwar P., 2005, Chem. Commun., 4601, 10.1039/b501304f

Fleischman S. G., 2003, Cryst. Growth Des., 3, 909, 10.1021/cg034035x

Almarsson Ö., 2004, PCT Int. Appl., 489, WO2004078161

Shan N., 2008, Drug Discovery Today, 13, 440, 10.1016/j.drudis.2008.03.004

Reddy L. S., 2006, Chem. Commun., 1369, 10.1039/b515510j

Babu N. J., 2007, Mol. Pharm., 4, 417, 10.1021/mp070014c

Childs S. L., 2007, Cryst. Growth Des., 7, 1291, 10.1021/cg060742p

Childs S. L., 2007, CrystEngComm, 9, 363, 10.1039/b703292g

Childs S. L., 2004, J. Am. Chem. Soc., 126, 13335, 10.1021/ja048114o

Remenar J. F., 2003, J. Am. Chem. Soc., 125, 8456, 10.1021/ja035776p

Morissette S. L., 2004, Adv. Drug Del. Rev, 56, 275, 10.1016/j.addr.2003.10.020

Blagden N., 2007, Adv. Drug Del. Rev., 59, 617, 10.1016/j.addr.2007.05.011

Caira M. R., 2007, Mol. Pharm., 4, 310, 10.1021/mp070003j

Jones W., 2006, MRS Bulletin, 31, 875, 10.1557/mrs2006.206

Trask A. V., 2006, Int. J. Pharm., 320, 114, 10.1016/j.ijpharm.2006.04.018

Trask A. V., 2005, Cryst. Growth Des., 5, 1013, 10.1021/cg0496540

Trask A. V., 2007, Mol. Pharm., 4, 301, 10.1021/mp070001z

Seefeldt K., 2007, J. Pharma. Sci., 96, 1147, 10.1002/jps.20945

Rodriguez-Hornedo N., 2006, Mol. Pharm., 3, 362, 10.1021/mp050099m

Dabros M., 2007, Angew. Chem., Int. Ed., 46, 4132, 10.1002/anie.200604830

Stahly G. P., 2007, Cryst. Growth Des., 7, 1007, 10.1021/cg060838j

Rizzo P., 2007, Chem. Mater., 19, 3864, 10.1021/cm071099c

Reddy L. S., 2007, Chem. Asian J., 2, 505, 10.1002/asia.200600359

Jayasankar A., 2007, Mol. Pharm., 4, 360, 10.1021/mp0700099

Linden A., 2006, Acta Crystallogr. Sect. C:, 62, o227−o230

Seefeldt K., 2007, J. Pharm. Sci., 96, 1147, 10.1002/jps.20945

Aakeroy C. B., 2006, Cryst. Growth Des., 6, 1033, 10.1021/cg0600492

Cowan J. A., 2006, Acta Crystallogr. Sect. C:, 62, 157, 10.1107/S0108270106004008

Bucar D.-K., 2007, J. Am. Chem. Soc., 129, 32, 10.1021/ja0671161

Zhu S., 2005, Cryst. Growth Des., 5, 1675, 10.1021/cg0501579

Bhogala B. R., 2005, Cryst. Growth Des., 5, 1683, 10.1021/cg058012p

Bhogala B. R., 2005, CrystEngComm, 7, 551, 10.1039/b509162d

Aakeroy C. B., 2005, Cryst. Growth Des., 5, 865, 10.1021/cg049682i

Zhang X. L., 2005, Cryst. Growth Des., 5, 617, 10.1021/cg0498251

Hammond R. B., 2003, J. Phys. Chem. B, 107, 11820, 10.1021/jp035010b

Lynch D. E., 2000, Crystal Engineering, 3, 71, 10.1016/S1463-0184(00)00029-0

Tukada H., 1997, Chem. Lett., 441, 10.1246/cl.1997.441

Bis J. A., 2006, Cryst. Growth Des., 6, 2648, 10.1021/cg060516f

Bis J. A., 2005, Cryst. Growth Des., 5, 1169, 10.1021/cg049622c

Bailey W. R. D., 2003, Chem. Commun., 9, 186

Sharma C. V. K., 1996, Chem. Commun., 2655, 10.1039/CC9960002655

Schmidt J., 1967, Int. J. Radiat. Biol., 13, 101

Etter M. C., 1991, J. Phys. Chem., 95, 4601, 10.1021/j100165a007

Etter M. C., 1991, J. Am. Chem. Soc., 113, 2586, 10.1021/ja00007a037

Etter M. C., 1990, J. Am. Chem. Soc., 112, 8415, 10.1021/ja00179a028

Etter M. C., 1990, Acc. Chem. Res., 23, 120, 10.1021/ar00172a005

Desiraju G. R., 2003, CrystEngComm, 5, 466, 10.1039/b313552g

Dunitz J. D., 2003, CrystEngComm, 5, 506, 10.1039/b315687g

Bond A. S., 2007, CrystEngComm, 9, 33

Wöhler F., 1844, Justus Liebigs Ann. Chem., 51, 153

Ling A. R., 1893, J. Chem. Soc. Trans., 63, 1314, 10.1039/CT8936301314

Anderson J. S., 1937, Nature, 140, 583, 10.1038/140583b0

Hoogsteen K., 1963, Acta Crystallogr., 16, 907, 10.1107/S0365110X63002437

Wenner W., 1949, J. Org. Chem., 14, 22, 10.1021/jo01153a004

Buck J. S., 1931, J. Am. Chem. Soc., 53, 2784, 10.1021/ja01358a052

Vanniekerk J. N., 1948, Acta Crystallogr., 1, 44, 10.1107/S0365110X48000107

Hall B., 1967, J. Phys. Chem., 71, 465, 10.1021/j100861a051

Pekker S., 2005, Nat. Mater., 4, 764, 10.1038/nmat1468

Vishweshwar P., 2006, J. Cryst. Growth Des., 6, 2429, 10.1021/cg060349j

Mondal R., 2006, Cryst. Growth Des., 6, 2507, 10.1021/cg060258m

Banerjee R., 2006, Cryst. Growth Des., 6, 1468, 10.1021/cg0601150

Barnett S. A., 2006, CrystEngComm, 8, 313, 10.1039/b600288a

Hosokawa T., 2004, Cryst. Growth Des., 4, 1195, 10.1021/cg049923m

Banerjee R., 2005, Cryst. Growth Des., 5, 2299, 10.1021/cg050125l

Petrosyan H. A., 2005, J. Cryst. Growth, 275, e1919−e1925

Trivedi D. R., 2003, CrystEngComm, 5, 358, 10.1039/b309216j

Sethuraman V., 2003, Cryst. Growth Des., 3, 823, 10.1021/cg030015j

Harris K. D. M., 2007, Supramol. Chem., 19, 47, 10.1080/10610270600977706

Ramon G., 2006, Supramol. Chem., 18, 59, 10.1080/10610270500373154

Enright G. D., 2004, Chem. Commun., 10, 1360, 10.1039/b401269k

Lee S. O., 2001, J. Am. Chem. Soc., 123, 12684, 10.1021/ja011467s

Special issue on Pharmaceutical cocrystalsMol. Pharm.2007,4, 299−486.

Bernstein J., 2002, Polymorphism in Molecular Crystals

Davey R. J., 2003, Chem. Commun., 1463, 10.1039/b303125j

cBradshaw, J.Ranitidine: In Annals of drug discovery,Lednicer, D. Ed.American Chemical Society: Washington DC, 1993, Vol.3, 45−81.

Hilfiker R., 2006, Polymorphism: in the Pharmaceutical Industry, 10.1002/3527607889

eSpecial Issue on Polymorphism in CrystalsCryst. Growth Des.2004,4, 1085−1444;

fSpecial Issue on Pharmaceutical solid polymorphism in drug development and regulationAdv. Drug Delivery Rev.2004,56, 235−418.

Allen F. H., 1993, Chem. Des. Automat. News, 8, 31

Allen F. H., 2002, Acta Crystallogr., 58, 380, 10.1107/S0108768102003890

Duchamp D. J., 1969, Acta Crystallogr., 25, 5, 10.1107/S0567740869001713

Cate A. T. T., 2004, J. Am. Chem. Soc., 126, 3801, 10.1021/ja039408x

Bruno G., 1980, Acta Crystallogr., 36, 1711, 10.1107/S0567740880007030

Bailey M., 1967, Acta Crystallogr., 22, 387, 10.1107/S0365110X67000751

Ermer O., 1988, J. Am. Chem. Soc., 110, 3747, 10.1021/ja00220a005

Leiserowitz L., 1983, Proc. Royal Soc. London Series A, 388, 133

Weinstein S., 1980, J. Am. Chem. Soc., 102, 2768, 10.1021/ja00528a042

Huang C. -M., 1973, J. Chem. Soc. Perkin Trans. 2, 503, 10.1039/p29730000503

Leiserowitz L., 1978, Acta Crystallogr., 34, 1230, 10.1107/S0567740878005270

McMahon J. A., 2005, Zeit. Kristallogr., 220, 340, 10.1524/zkri.220.4.340.61624

Infantes L., 2004, Struc.Chem., 15, 173, 10.1023/B:STUC.0000021525.74750.fa

Arora K. K., 2003, J. Org. Chem., 68, 9177, 10.1021/jo034434z

Shattock T. R., 2005, Cryst. Growth Des., 5, 2046, 10.1021/cg0501985

Steiner T., 2001, Acta Crystallogr., Sect. B: Struct. Sci., 57, 103, 10.1107/S0108768100014348

Vishweshwar P., 2003, Cryst. Growth Des., 3, 783, 10.1021/cg034037h

Vishweshwar P., 2002, J. Org. Chem., 67, 556, 10.1021/jo0162484

Etter M. C., 1990, J. Chem. Soc., Chem. Commun., 589, 10.1039/c39900000589

Aakeroy C. B., 2002, J. Am. Chem. Soc., 124, 14425, 10.1021/ja027845q

Bhogala B. R., 2002, Cryst. Growth Des., 2, 325, 10.1021/cg025537y

Aakeroy C. B., 2003, Cryst. Growth Des., 3, 159, 10.1021/cg025593z

Aakeroy C. B., 2001, Angew. Chem. Int. Ed., 40, 3240, 10.1002/1521-3773(20010903)40:17<3240::AID-ANIE3240>3.0.CO;2-X

Vishweshwar P., 2003, Cryst. Growth Des., 3, 783, 10.1021/cg034037h

Reddy L. S., 2004, Cryst. Growth Des., 4, 89, 10.1021/cg034106s

Videnovaadrabinska V., 1995, J. Chem. Crystallogr., 25, 823, 10.1007/BF01671077

Leiserowitz L., 1977, Acta Crystallogr., Sect. B: Struct. Sci., 33, 2719, 10.1107/S0567740877009376

Bis J. A., 2007, Mol. Pharm., 4, 401, 10.1021/mp070012s

Varughese S., 2006, Chem. Eur. J., 12, 1597, 10.1002/chem.200500570

Vishweshwar P., 2003, CrystEngComm, 5, 164, 10.1039/B304078J

Papaefstathiou G. S., 2001, Org. Lett., 3, 3835, 10.1021/ol0165948

Leiserowitz L., 1976, Acta Crystallogr. B, 32, 775, 10.1107/S0567740876003968

Allen F. H., 1998, Chem. Commun., 1043, 10.1039/a801424h

Allen F. H., 1999, New. J. Chem., 2, 5

Infantes L., 2004, Chem. Commun., 1166, 10.1039/b402939a

Infantes L., 2005, Kristallogr., 220, 333

ahttp://www.pharmacytimes.com/issues/articles/2007−05_4629.asp

bhttp://www.rxlist.com/top200.htm.

Basavoju S., 2006, Cryst. Growth Des., 6, 2699, 10.1021/cg060327x

Childs S. L., 2008, CrystEngComm, 10, 856, 10.1039/b715396a

Childs S. L., 2007, Cryst. Growth Des., 7, 1291, 10.1021/cg060742p

Borthwick P. W., 1980, Acta Crystallogr. B, 36, 628, 10.1107/S0567740880003950

Boenigk D., 1988, J. Am. Chem. Soc., 110, 2135, 10.1021/ja00215a021

Cowan J. A., 2003, Acta Crystallogr., 59, 794, 10.1107/S0108768103024984

Trask A. V., 2005, Top. Curr. Chem., 254, 41, 10.1007/b100995

SAINT, Version 6.02; Bruker AXS, Inc., Analytical X-ray Systems, 5465 East Cheryl Parkway, Madison, WI 53711−5373, 2000.

SADABS [Area-Detector Absorption Correction]; Siemens Industrial Automation, Inc.: Madison, WI, 1996.

Sheldrick G. M., 1997, SHELXTL; University of Göttingen: Göttingen, Germany

CSD, August 2007 release including January 2008 update. Search parameters: organics only, no ions, 3D coordinates determined, R <7.5%.

Frankenbach G. M., 1992, Chem. Mater., 4, 272, 10.1021/cm00020a011

Sosnovsky G., 1994, Pharma. Sci., 83, 999, 10.1002/jps.2600830715

Nather C., 2006, Angew. Chem. Int. Ed., 45, 6381, 10.1002/anie.200601468

Hong-Jie Z., 2006, J. Med. Chem., 49, 693, 10.1021/jm0509492

15 entries in CSD (Refcodes: BEQWAV, GEHROB, GUTSAP, HAKVEV, IDUBUF, MOBZUY, SOFHIE, VEFVEI, VEFVIM, XAPMAC, WEPDIF, DEXTOQ, XIFQEJ ODOBIT ODOBIT01).

Takusagawa F., 1976, Acta Crystallogr. Sect. B, 32, 1925, 10.1107/S0567740876006754

Kutoglu A., 1983, Acta Crystallogr. Sect. C, 39, 232, 10.1107/S0108270183004230

Organic salts with isonicotinate ion. Refcodes: AJECAT, FETXIM, REFFIS, XECDUF and YERXUP.

Jebas S. R., 2006, Acta Crystallogr. Sect. E, 62, o5621, 10.1107/S1600536806046812

Zhu J, 2004, Chinese J. Struct. Chem., 23, 417

Stahl P. H., 2002, Handbook of pharmaceutical salts: properties, selection, and use

Johnson S. L., 1965, J. Phys. Chem., 69, 74, 10.1021/j100885a013

Childs S. L., 2007, Mol. Pharm., 4, 323, 10.1021/mp0601345

Gridunova G. V., 1982, Kristallografiya, 27, 267

Kariuki B. M., 2000, J. Angew. Chem. Int. Ed., 39, 4485, 10.1002/1521-3773(20001215)39:24<4485::AID-ANIE4485>3.0.CO;2-T