Abstract
Structures of different classes of organic crystal hydrates are considered and their structural classification is presented based on the dimensionality and planarity of the included (Н2О) n motif (water associate). The structural data are generalized with respect to the proton excess of the water associate.
Similar content being viewed by others
References
R. Ludwig, Angew. Chem., Int. Ed., 40, 1808 (2001).
F. H. Allen, Acta Crystallogr., Sect. B, 58, 380 (2002).
G. P. Stahly, Cryst. Growth Des., 7, 1007 (2007).
Z. Dega-Szafran, G. Dutkiewicz, Z. Kosturkiewicz, and M. Szafran, J. Mol. Struct., 985, 219 (2011).
A. Symington, R. A. Cox, and M. A. Fernandez, Z. Phys. Chem., 224, 1219 (2010).
M. N. Romanis, A. G. Zogka, V. C. Papadimitriou, and P. Papagiannakopoulos, J. Phys. Chem. A, 116, 2198 (2012).
A. Symington, L. M. Leow, P. T. Griffiths, and R. A. Cox, J. Phys. Chem. A, 116, 5990 (2012).
A. S. Monin and Yu. A. Shishkov, Usp. Fiz. Nauk, 170, 419 (2000).
E. A. Zheligovskaya and G. G. Malenkov, Usp. Khim., 75, 64 (2006).
L. Infantes and S. Motherwell, CrystEngComm, 4, 454 (2002).
K. Fucke and J. W. Steed, Water, 2, 333 (2010).
F. H. Allen, Chem. Soc. Rev., 33, 463 (2004).
F. H. Allen, Cryst. Rev., 10, 3 (2004).
W. D. S. Motherwell, Cryst. Rev., 14, 97 (2008).
J. van der Streek and W. D. S. Motherwell, Acta Crystallogr., Sect. B, 61, 504 (2005).
L. N. Kuleshova and M. Yu. Antipin, Usp. Khim., 68, 3 (1999).
W. D. M. Hoffman, L. N. Kuleshova, and M. Yu. Antipin, Cryst. Growth Des., 4, 1395 (2004).
A. V. Vologzhanina, A. A. Korlyukov, and M. Yu. Antipin, Acta Crystallogr., Sect. B, 64, 448 (2008).
L. N. Kuleshova, M. Yu. Antipin, and I. V. Komkov, J. Mol. Struct., 647, 41 (2003).
J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press, Oxford (2002).
A. Gavezzotti, CrystEngComm, 10, 389 (2008).
A. Nangia, CrystEngComm, 4, 93 (2002).
I. A. Baburin, V. A. Blatov, L. Carlucci, et al., Cryst. Growth Des., 8, 519 (2008).
P. M. Zorkii and P. N. Oleinikov, Zh. Fiz. Khim., 74, 1944 (2000).
P. M. Zorkii and P. N. Oleinikov, J. Struct. Chem., 42, 24 (2001).
A. T. Hulme and S. L. Price, J. Chem. Theory Comput., 3, 1597 (2007).
A. V. Dzyabchenko, Zh. Fiz. Khim., 82, 1861 (2008).
A. A. Korlyukov and M. Yu. Antipin, Usp. Khim., 81, 105 (2012).
A. Parkin, A. Collins, C. J. Gilmore, and C. C. Wilson, Acta Crystallogr., Sect. B, 64, 66 (2008).
A. Simperler, S. W. Watt, P. A. Bonnet, et al., CrystEngComm, 8, 589 (2006).
Yu. L. Slovokhotov, I. S. Neretin, and J. A. K. Howard, New J. Chem., 28, 967 (2004).
A. M. Banaru, P. M. Zorkii, and A. E. Obodovskaya, Kristallografiya, 52, 661 (2007).
L. Infantes, J. Chisholm, and S. Motherwell, CrystEngComm, 5, 480 (2003).
L. Infantes, L. Fabian, and W. D. S. Motherwell, CrystEngComm, 9, 65 (2007).
L.G. Kuz'mina, Koord. Khim., 25, 643 (1999).
T. Steiner, Angew. Chem., Int. Ed., 41, 48 (2002).
Yu. A. Dyadin, I. S. Terekhova, and T. V. Rodionova, J. Struct. Chem., 40, 645–653 (1999).
K. Shin, I. L. Moudrakovski, M. D. Davari, et al., CrystEngComm, 16, 7209 (2014).
D. Londono, W. F. Kuhs, and J. L. Finney, Nature, 332, 141 (1988).
E. A. Zheligovskaya, J. Struct. Chem., 45, 988 (2004).
E. A. Kurnosov, V. Yu. Komarov, V. I. Voronin, et al., Angew. Chem., Int. Ed., 43, 2922 (2004).
W. B. Pearson, The Crystal Chemistry and Physics of Metals and Alloys, Wiley-Interscience, New York (1972).
V. R. Belosludov, Yu. A. Dyadin, and M. Yu. Lavrentiev, Theoretical Models of Clathrate Formation [in Russian], Nauka SO RAN, Novosibirsk (1991).
J.-H. Cha, K. Shin, and S. Choi, J. Phys. Chem., 112, 13332 (2008).
W. Hesse and M. Jansen, Z. Anorg. Allg. Chem., 595, 115 (1991).
T. Ogata, T. Tsuda, S. Amano, et al., Chem. Eng. Sci., 65, 1616 (2010).
T. Kawamura, S. Takeya, M. Ohtake, and Y. Yamamoto, Chem. Eng. Sci., 66, 2417 (2011).
A. Delahaye, L. Fournaison, and J. Guilpart, Int. J. Refrig., 33, 1639 (2010).
S. Liang and P. G. Kusalik, Chem. Phys. Lett., 494, 123 (2010).
T. Koga, J. Wong, M. K. Endoh, et al., Langmuir, 26, 4627 (2010).
L. S. Aladko, Yu. A. Dyadin, T. V. Rodionova, and I. S. Terekhova, J. Struct. Chem., 43, 990–994 (2002).
Y. Kamata, H. Oyama, W. Shimada, et al., Jpn. J. Appl. Phys., 43, 362 (2004).
Y. Kamata, Y. Yamakoshi, T. Ebinuma, et al., Energy Fuels, 19, 1717 (2005).
M. Oshima, W. Shimada, S. Hashimoto, et al., Chem. Eng. Sci., 65, 5442 (2010).
I. L. Samoilovich and A. L. Talis, Dokl. Akad. Nauk, 420, 472 (2008).
O. Delgado-Friedrichs and M. O'Keeffe, Acta Crystallogr., Sect. A, 66, 637 (2010).
V. Yu. Komarov, S. F. Solodovnikov, E. V. Grachev, et al., Cryst. Rev., 13, 257 (2007).
E. Dendy Sloan Jr., Ind. Eng. Chem. Res., 39, 3123 (2000).
H. Tanaka, Theor. Comput. Chem., 7, 533 (1999).
V. I. Kosyakov and T. M. Polyanskaya, J. Struct. Chem., 40, 239 (1999).
A. Wlodarczyk, P. F. McMillan, and S. A. Greenfield, Chem. Soc. Rev., 35, 890 (2006).
P. Agre, Angew. Chem., Int. Ed., 43, 4278 (2004).
G. Hummer, J. C. Rasaiah, and J. P. Noworyta, Nature, 414, 188 (2001).
K. Koga, G. T. Gao, H. Tanaka, and X. C. Zeng, Nature, 412, 802 (2001).
K. A. Udachin and Y. Lipkowski, J. Struct. Chem., 43, 705–709 (2002).
H. Birkedal, D. Schwarzenbach, and P. Pattison, Angew. Chem., Int. Ed., 41, 754 (2002).
M. A. Kellard, Energy Fuels, 20, 825 (2006).
H. Ajiro, Y. Takemoto, M. Akashi, et al., Energy Fuels, 24, 6400 (2010).
R. Masoudi and B. Tohidi, J. Pet. Sci. Eng., 74, 132 (2010).
W. Clegg and G. S. Nichol, Acta Crystallogr., Sect. E, 60, o1433 (2004).
F. Liebau, Structural Chemistry of Silicates, Springer-Verlag, Berlin, Heidelberg, New York, Tokyo (1985).
K. A. Kovnir and A. V. Shevelkov, Usp. Khim., 73, 999 (2004).
A. Muller, E. Beckmann, H. Boegge, et al., Angew. Chem., Int. Ed., 41, 1162 (2002).
M. Mascal, L. Infantes, and J. Chisholm, Angew. Chem., Int. Ed., 45, 32 (2006).
O. V. Grineva, J. Struct. Chem., 48, 753 (2007).
P. Gilli, L. Pretto, V. Bertolasi, and G. Gilli, Acc. Chem. Res., 42, 33 (2009).
T. Asaji, M. Hoshino, H. Ishida, et al., Hyperfine Interact., 198, 85 (2010).
R. Viswanathan, A. Asenio, and J. J. Dannenberg, J. Phys. Chem. A, 108, 9205 (2004).
A. Mojaheri, J. Mol. Struct., 678, 201 (2001).
K. A. Lysenko and M. Yu. Antipin, Izv. Akad. Nauk, Ser. Khim., 1, 1 (2006).
S. J. Grabowski, W. A. Sokalski, E. Dyguda, and J. Leszcynski, J. Phys. Chem. B, 110, 6444 (2006).
P. Gilli, V. Bertolasi, L. Pretto, and G. Gilli, J. Mol. Struct., 790, 40 (2006).
P. Gilli, V. Bertolasi, V. Ferretti, and G. Gilli, J. Am. Chem. Soc., 122, 10405 (2000).
A. L. Gillon, N. Feeder, R. J. Davey, and R. Storey, Cryst. Growth Des., 3, 663 (2003).
T. Uyar, M. A. Hunt, H. S. Gracz, and A. E. Tonelli, Cryst. Growth Des., 6, 1113 (2006).
L. X. Song, L. Bai, X. M. Xu, et al., Coord. Chem. Rev., 253, 1276 (2009).
Yu. Kuji, A. Yamasaki, and Yu. Yanagisawa, Energy Fuels, 20, 2198 (2006).
M.-X. Wang and H.-B. Yang, J. Am. Chem. Soc., 126, 15412 (2004).
Y. Miyahara, K. Abe, and T. Inazu, Angew. Chem., Int. Ed., 41, 3020 (2002).
L. Fabian, J. A. Chisholm, P. T. A. Galek, et al., Acta Crystallogr., Sect. B, 64, 504 (2008).
S. Hovmoller, T. Zhou, and T. Ohlson, Acta Crystallogr., Sect. D, 58, 768 (2002).
D. E. Braun, P. G. Karamertzanis, and S. L. Price, Chem. Commun., 47, 5443 (2011).
F. Tian, H. Qu, M. Louhi-Kultanen, and J. Rantanen, J. Pharm. Sci., 99, 753 (2010).
N. Boubals, M. G. B. Drew, C. Hill, et al., J. Chem. Soc., Dalton Trans., 1, 55 (2002).
M. C. Kozlowski, Z. Xu, and A. G. Santos, Terahedron, 57, 4537 (2001).
V. A. Palyulin, O. M. Grek, C. B. Emets, et al., Dokl. Akad. Nauk, 370, 53 (2000).
R. G. Kostyanovsky, K. A. Lyssenko, D. A. Lenev, and I. A. Bronzova, Tetrahedron: Asymmetry, 13, 2697 (2002).
G. Impellizzeri, G. Pappalardo, F. D'Alessandro, et al., Eur. J. Org. Chem., 6, 1065 (2000).
S. K. Ghosh and P. K. Bharadwaj, Eur. J. Inorg. Chem., 7, 1341 (2006).
O. Ermer and J. Neudorfl, Chem.–Eur. J., 7, 4961 (2001).
H. Steinmetz, N. Glaser, E. Herdtweck, et al., Angew. Chem., Int. Ed., 43, 4888 (2004).
A. K. Bauri, F. Sabine, H. J. Lindner, and S. K. Nayak, Acta Crystallogr., Sect. E, 62, o2321 (2006).
B. Sridhar and K. Ravikumar, Crystallogr. Rep., 55, 240 (2010).
J. Marti-Rujas, A. Morte-Rodenas, F. Guo, et al., Cryst. Growth Des., 10, 3176 (2010).
M. J. Hardie, R. M. Mills, and S. J. Sumby, Org. Biomol. Chem., 2, 2958 (2004).
S. Janeda and D. Mootz, Z. Naturforsch., Teil B, 54, 103 (1999).
T. Murata, Y. Morita, and K. Nakasuji, Tetrahedron, 61, 6056 (2005).
Y. Cai, Z. Zhou, L. Qiu, et al., Acta Crystallogr., Sect. E, 58, o167 (2002).
D. Font, A. Linden, M. Heras, and J.-M. Villalgordo, Tetrahedron, 62, 1433 (2006).
M. M. Konopleva, I. Matlawska, M. Wojcinska, et al., J. Nat. Prod., 69, 394 (2006).
B. Venkataramanan, W. L. G. James, J. J. Vittal, and V. Suresh, Cryst. Growth Des., 4, 553 (2004).
G. Smith, U. D. Wermuth, P. C. Healy, and J. M. White, Acta Crystallogr., Sect. C, 62, o203 (2006).
Y.-P. Cai, G.-B. Li, G.-P. He, et al., Acta Crystallogr., Sect. E, 60, o2062 (2004).
X.-C. Huang, M.-H. Zhen, and S. W. Ng, Acta Crystallogr., Sect. E, 60, o939 (2004).
N. Fridman, M. Kapon, and M. Kaftory, Acta Crystallogr., Sect. C, 60, o44 (2004).
M. Wiebcke and J. Felsche, Acta Crystallogr., Sect. C, 57, 306 (2001).
M. Wiebcke and J. Felsche, Acta Crystallogr., Sect. C, 56, 901 (2000).
J. R. Long and O. M. Yaghi, Chem. Soc. Rev., 38, 1213 (2009).
N. Guillon, F. Millage, and R. I. Walton, Chem. Commun., 47, 713 (2011).
X. Hao, S. Parkin, and C. P. Brock, Acta Crystallogr., Sect. B, 61, 689 (2005).
A. Yu. Manakov, V. I. Voronin, A. V. Kurnosov, et al., J. Incl. Phenom. Macrocycl. Chem., 48, 11 (2004).
K. Kobayashi, S. Kimura, E. Togawa, and M. Wada, Carbohydr. Polym., 86, 975 (2011).
M. Oresic, A. Danilovski, M. Dumic, and N. Kosutic-Hulita, J. Heterocycl. Chem., 38, 785 (2001).
V. Yu. Komarov, S. F. Solodovnikov, and A. V. Kurnosov, J. Struct. Chem., 46, S181 (2005)
A. M. Banaru and Yu. L. Slovokhotov, J. Struct. Chem., 50, 735 (2009).
A. M. Banaru and Yu. L. Slovokhotov, Vestn. Mosk. Univ., Ser. 2: Khim., 51, 435 (2010).
A. Banaru and Yu. L. Slovokhotov, CrystEngComm, 12, 1054 (2010).
A. Banaru, CrystEngComm, 13, 212 (2011).
R. V. Galiulin, Crystal-graphic Geometry [in Russian], KomKniga, Moscow (2005).
A. M. Banaru and G. A. Banaru, Vestn. Mosk. Univ., Ser. 2: Khim., 52, 192 (2011).
A. M. Banaru and G. A. Banaru, Vestn. Mosk. Univ., Ser. 2: Khim., 53, 8 (2012).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © 2015 A. M. Banaru, Yu. L. Slovokhotov.
__________
Translated from Zhurnal Strukturnoi Khimii, Vol. 56, No. 5, pp. 1024–1040, September–October, 2015.
To the memory of M. Yu. Antipin, Corresponding Member of the Russian Academy of Sciences
Rights and permissions
About this article
Cite this article
Banaru, A.M., Slovokhotov, Y.L. Crystal hydrates of organic compounds. J Struct Chem 56, 967–982 (2015). https://doi.org/10.1134/S0022476615050212
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476615050212