%0 Journal Article %1 ISI:000327898500024 %A Moghimi, A. %A Khavasi, H. R. %A Dashtestani, F. %A Kordestani, D. %A Behboodi, E. %A Maddah, B. %C 233 SPRING ST, NEW YORK, NY 10013-1578 USA %D 2013 %I MAIK NAUKA/INTERPERIODICA/SPRINGER %J JOURNAL OF STRUCTURAL CHEMISTRY %K X-ray acid.} bonding; caffeine; chemistry; crystal diffraction; dipicolinic hydrogen proton single transfer; {crystal %N 5 %P 990-995 %R 10.1134/S0022476613050247 %T A COCRYSTAL OF CAFFEINE AND DIPICOLINIC ACID: SYNTHESIS, CHARACTERIZATION, X-RAY CRYSTALLOGRAPHY, AND SOLUTION STUDIES %V 54 %X A reaction between caffeine (caff) and dipicolinic acid = 2,6-pyridine dicarboxylic acid (pydc.H-2) in water results in the formation of a cocrystal compound (pydc.H-2.H2O)(caff) 1. The characterization of the resulting crystallohydrate is performed using H-1, C-13 NMR and IR spectroscopy and X-ray crystallography. X-ray crystal structure analysis reveals the presence of both starting materials and water in the lattice. It also indicates intensive intermolecular H bonding interactions between carboxylic acid, caffeine, and water as well as pi-pi stacking between the pydc.H-2 and caff rings as constituents of the cocrystal. The hydrogen bonding and non-covalent interactions play roles in the formation of the cocrystal. The crystal system is triclinic with the space group P-1 and two formula units per unit cell. The unit cell parameters are a = 6.906(2) , b = 8.451(3) , c = 14.68 (4) with alpha = 81.51(3)A degrees, beta = 78.47(3)A degrees, and gamma = 78.14(3)A degrees. The final R value is 0.0660 for 7943 measured reflections.

@article{ISI:000327898500024, abstract = {{A reaction between caffeine (caff) and dipicolinic acid = 2,6-pyridine dicarboxylic acid (pydc.H-2) in water results in the formation of a cocrystal compound (pydc.H-2.H2O)(caff) 1. The characterization of the resulting crystallohydrate is performed using H-1, C-13 NMR and IR spectroscopy and X-ray crystallography. X-ray crystal structure analysis reveals the presence of both starting materials and water in the lattice. It also indicates intensive intermolecular H bonding interactions between carboxylic acid, caffeine, and water as well as pi-pi stacking between the pydc.H-2 and caff rings as constituents of the cocrystal. The hydrogen bonding and non-covalent interactions play roles in the formation of the cocrystal. The crystal system is triclinic with the space group P-1 and two formula units per unit cell. The unit cell parameters are a = 6.906(2) , b = 8.451(3) , c = 14.68 (4) with alpha = 81.51(3)A degrees, beta = 78.47(3)A degrees, and gamma = 78.14(3)A degrees. The final R value is 0.0660 for 7943 measured reflections.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{233 SPRING ST, NEW YORK, NY 10013-1578 USA}}, affiliation = {{Moghimi, A (Reprint Author), Islamic Azad Univ, Tehran North Branch, Dept Chem, Tehran, Iran. Moghimi, A.; Dashtestani, F.; Behboodi, E., Islamic Azad Univ, Tehran North Branch, Dept Chem, Tehran, Iran. Khavasi, H. R., Shahid Beheshti Univ, Dept Chem, GC, Tehran, Iran. Kordestani, D., Razi Univ, Dept Chem, Kermanshah, Iran. Maddah, B., Imam Hossein Univ, Dept Chem, Tehran, Iran.}}, author = {Moghimi, A. and Khavasi, H. R. and Dashtestani, F. and Kordestani, D. and Behboodi, E. and Maddah, B.}, author-email = {{f.dashtestani@gmail.com}}, biburl = {https://www.bibsonomy.org/bibtex/2c46b76c26ea29a08cd3c55a76435ec0d/hkhavasi}, cited-references = {{Aakeroy CB, 2005, CRYSTENGCOMM, V7, P439, DOI 10.1039/b505883j. Benoit R. L., 1985, CAN J CHEM, V63, P2821. Bucar DK, 2007, MOL PHARM, V4, P339, DOI 10.1021/mp070004b. Bucar DK, 2007, CHEM COMMUN, P525, DOI 10.1039/b611749j. Bucar DK, 2010, J CHEM CRYSTALLOGR, V40, P933, DOI {[}10.1007/s10870-010-9766-y, 10.1007/s10870.010.9766.y]. Lynch DE, 1998, AUST J CHEM, V51, P403, DOI 10.1071/C97201. LYNCH DE, 1994, AUST J CHEM, V47, P1097. Lynch DE, 1998, AUST J CHEM, V51, P813, DOI 10.1071/C98099. Moghimi A, 2005, Z ANORG ALLG CHEM, V631, P902, DOI 10.1002/zaac.200400433. Moghimi A, 2005, Z ANORG ALLG CHEM, V631, P160, DOI 10.1002/zaac.200400280. Moghimi A., 2002, CAN J CHEM, V80, P1635. Poltev VI, 2004, J MOL STRUC-THEOCHEM, V709, P123, DOI 10.1016/j.theochem.2003.10.074. Ranjbar R. Z., 2007, J MOL STRUCT, V826, P29. Schultheiss N, 2009, CRYST GROWTH DES, V9, P2950, DOI 10.1021/cg900129f. Sheldrick G. M., 1997, SHELX 97 PROGRAM CRY. STADLER RH, 1995, J AGR FOOD CHEM, V43, P1332, DOI 10.1021/jf00053a038. {[}Anonymous], 2005, STOE CIE X RED 1 28B. {[}Anonymous], 2004, STOE CIE X SHAPE 2 0. Vishweshwar P, 2006, J PHARM SCI-US, V95, P499, DOI 10.1002/jps.20578. Watson JM, 2000, DIABETES CARE, V23, P455, DOI 10.2337/diacare.23.4.455. Silva V., 2002, US Patent, Patent No. {[}0150597A1, 0150597].}}, doc-delivery-number = {{264RP}}, doi = {{10.1134/S0022476613050247}}, eissn = {{1573-8779}}, funding-acknowledgement = {{Imam Hossein University}}, funding-text = {{We gratefully acknowledge the support of this work by the Imam Hossein University.}}, interhash = {b8f34f3a72d1b2c83c92376b21f48ea2}, intrahash = {c46b76c26ea29a08cd3c55a76435ec0d}, issn = {{0022-4766}}, journal = {{JOURNAL OF STRUCTURAL CHEMISTRY}}, journal-iso = {{J. Struct. Chem.}}, keywords = {X-ray acid.} bonding; caffeine; chemistry; crystal diffraction; dipicolinic hydrogen proton single transfer; {crystal}, keywords-plus = {{PROTON-TRANSFER COMPOUND; MOLECULAR COCRYSTALS; CARBOXYLIC-ACIDS; 2,6-PYRIDINEDICARBOXYLIC ACID; CRYSTAL-STRUCTURES; CO-CRYSTALS; 2-AMINOPYRIMIDINE; ADDUCTS}}, language = {{English}}, month = {{SEP}}, number = {{5}}, number-of-cited-references = {{21}}, pages = {{990-995}}, publisher = {{MAIK NAUKA/INTERPERIODICA/SPRINGER}}, research-areas = {{Chemistry}}, times-cited = {{2}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{A COCRYSTAL OF CAFFEINE AND DIPICOLINIC ACID: SYNTHESIS, CHARACTERIZATION, X-RAY CRYSTALLOGRAPHY, AND SOLUTION STUDIES}}, type = {{Article}}, unique-id = {{ISI:000327898500024}}, usage-count-last-180-days = {{0}}, usage-count-since-2013 = {{12}}, volume = {{54}}, web-of-science-categories = {{Chemistry, Inorganic \& Nuclear; Chemistry, Physical}}, year = {{2013}} }