• 1
    Bond AD. 2007. What is a co-crystal? CrystEngComm 9: 833834.
  • 2
    Byrn S, Pfeiffer R, Stephenson G, Grant DJW, Gleason WB. 1994. Solid-state pharmaceutical chemistry. Chem Mater 6: 11481158.
  • 3
    Vishweshwar P, McMohan JA, Bis JA, Zaworotko MJ. 2006. Pharmaceutical co-crystals. J Pharm Sci 95: 499516 and references cited within.
  • 4
    Schultheiss N, Newman A. 2009. Pharmaceutical cocrystals and their physicochemical properties. Cryst Growth Des 9: 29502967.
  • 5
    Bhatt PM, Azim Y, Thakur TS, Desiraju GR. 2009. Co-crystals of the anti-HIV drugs lamivudine and zidovudine. Cryst Growth Des 9: 951957.
  • 6
    Herrmann M, Förter-Barth U, Kröbe H, Kempa PB, Juez-Lorenzo MM, Doyle MJ. 2009. Co-crystallization and characterization of pharmaceutical ingredients. Part Part Syst Charact 26: 151156.
  • 7
    Stanton MK, Bak A. 2008. Physicochemical properties of pharmaceutical co-crystals: A case study of ten AMG 517 co-crystals. Cryst Growth Des 8: 38563862.
  • 8
    Jones W, Motherwell WDS, Trask AV. 2006. Pharmaceutical cocrystals: An emerging approach to physical property enhancement. MRS Bull 31: 875879.
  • 9
    Trask AV, Motherwell WDS, Jones W. 2005. Pharmaceutical cocrystallization: Engineering a remedy for caffeine hydration. Cryst Growth Des 5: 10131021.
  • 10
    Good DJ, Rodríguez-Hornedo N. 2009. Solubility advantage of pharmaceutical cocrystals. Cryst Growth Des 9: 22522264.
  • 11
    NcNamara DP, Childs SL, Giordano J, Iarriccio A, Cassidy J, Shet MS, Mannion R, O'Donnell E, Park A. 2006. Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API. Pharm Res 23: 18881897.
  • 12
    Karki S, Friščíc T, Fábián L, Laity PR, Day GM, Jones W. 2009. Improving mechanical properties of crystalline solids by cocrystal formation: New compressible forms of paracetamol. Adv Mater 21: 39053909.
  • 13
    Desiraju GR. 1995. Supramolecular synthons in crystal engineering: A new organic synthesis. Angew Chem Int Ed 34: 23112327.
  • 14
    Thalladi VR, Goud BS, Hoy VJ, Allen FH, Howard JAK, Desiraju GR. 1996. Supramolecular synthons in crystal engineering. Structure simplification, synthon robustness and supramolecular retrosynthesis. Chem Commun 401402.
  • 15
    Nangia A, Desiraju GR. 1998. Supramolecular synthons and pattern recognition. Top Curr Chem 198: 5895.
  • 16
    Walsh RDB, Bradner MW, Fleishman S, Morales LA, Moulton B, Rodríguez-Hornedo N, Zaworotko MJ. 2003. Crystal engineering of the composition of pharmaceutical phases. Chem Commun 186187.
  • 17
    Sarma B, Nath NK, Bhogala BR, Nangia A. 2009. Synthon competition and cooperation in molecular salts of hydroxybenzoic acids and aminopyridines. Cryst Growth Des 9: 15461557.
  • 18
    Pedireddi VR, Arora KK. 2003. A rational study of crystal engineering of supramolecular sassemblies of 1,2,4,5-benzenetetracarboxylic acid. J Org Chem 68: 91779185.
  • 19
    Bucar D-K, Henry RF, Lou X, Duerst RW, MacGillivray LR, Zhang GGZ. 2009. Cocrystals of caffeine and hydroxybenzoic acids composed of multiple supramolecular heterosynthons: Screening via solution-mediated phase transformation and structural characterization. Cryst Growth Des 9: 19321943.
  • 20
    Vishweshwar P, Nangia A, Lynch VM. 2003. Molecular complexes of homologous alkanedicarboxylic acids with isonicotinamide: X-ray crystal structures, hydrogen bond synthons, and melting point alternation. Cryst Growth Des 3: 783790.
  • 21
    Allen FH, Kennard O. 1993. 3D search and research using the Cambridge Structural Database. Chem Des Auto News 8: 3137.
  • 22
    Remenar JF, Morissette SL, Peterson ML, Moulton B, MacPhee JM, Guzmán HR, Almarsson Ö. 2003. Crystal engineering of novel cocrystals of a triazole drug with 1,4-dicarboxylic acids. J Am Chem Soc 125: 84568457.
  • 23
    Dawson GW, Jue SG, Brogden RN. 1984. Alprazolam. A review of its pharmacodynamic properties and efficacy in the treatment of anxiety and depression. Drugs 27: 132147.
  • 24
    VonVoigtlander PF, Straw RN. 1985. Alprazolam: Review of pharmacological, pharmacokinetic, and clinical data. Drug Dev Res 6: 112.
  • 25
    Sheldrick GM. 1994. SADABS: Siemens Area Detector Absorption Correction Program. University of Gottingen. Germany.
  • 26
    Sheldrick GM. 1998. SHELX97 programs for crystal structure analysis. Version 97-2.
  • 27
    Spek AL. 1990. PLATON Molecular Geometry Program. Acta Crystallogr A46: C34.
  • 28
    Aullón G, Bellamy D, Orpen AG, Brammer L, Bruton EA. 1998. Metal-bound chlorine often accepts hydrogen bonds. Chem Commun 653654.
  • 29
    Banerjee R, Desiraju GR, Mondal R, Howard JAK. 2004. Organic chlorine as a hydrogen-bridge acceptor: Evidence for the existence of intramolecular O[BOND]Hequation imageCl[BOND]C Interactions in some gem-alkynols. Chem Eur J 10: 33733383.
  • 30
    Papadopoulos N, Avranas A. 1991. Dissociation of salicylic acid, 2,4-, 2,5-, and 2,6-dihydroxybenzoic acids in 1-propanol -water mixtures at 25°C. J Solut Chem 20: 293300.
  • 31
    Thalladi VR, Weiss H-C, Bläser D, Boese R, Nangia A, Desiraju GR. 1998. C[BOND]Hequation imageF interactions in the crystal structures of some fluorobenzenes. J Am Chem Soc 120: 87028710.
  • 32
    Refcode CIZQAD01. The details of the interactions present in the assembly are provided in the supplementary information.
  • 33
    Shuvalov RR, Burns PC. 2003. A new polytype of orthoboric acid, H3BO3-3T. Acta Crystallogr C59: i47i49.
  • 34
    Pedireddi VR, SeethaLekshmi N. 2004. Boronic acids in the design and synthesis of supramolecular assemblies. Tetrahedron Lett 45: 19031906.
  • 35
    Aakeröy CB, Desper J, Levin B. 2005. Crystal engineering gone awry and the emergence of the boronic acid–carboxylate synthon. CrystEngComm 7: 102107.
  • 36
    Pedireddi VR, Reddy DS, Goud BS, Craig DC, Rae AD, Desiraju GR. 1994. The nature of halogenequation imagehalogen interactions and the crystal structure of 1,3,5,7-tetraiodoadamantane. J Chem Soc Perkin Trans 2: 23532360.
  • 37
    Nangia A, Desiraju GR. 1999. Pseudopolymorphism: Occurences of hydrogen bonding organic solvents in molecular crystals. Chem Commun 605606.
  • 38
    SPARC online calculator.