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Volumn 4, Issue 3, 2007, Pages 317-322

Cocrystal or salt: Does it really matter?

Author keywords

Cocrystal; Crystal lattice; Crystal prediction; Hydrogen bonding; Salt

Indexed keywords

ANION; BENZIMIDAZOLE; BENZYL THIOCYANATE; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; PYRIDINIUM DERIVATIVE; SODIUM CHLORIDE;

EID: 34250863849     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp060126o     Document Type: Article
Times cited : (425)

References (38)
  • 3
    • 21344459003 scopus 로고    scopus 로고
    • Supramolecular reagents: Versatile tools for non-covalent synthesis
    • Aakeröy, C. B.; Desper, J.; Urbina, J. F. Supramolecular reagents: versatile tools for non-covalent synthesis. ChemComm, 2005, 2820.
    • (2005) ChemComm , pp. 2820
    • Aakeröy, C.B.1    Desper, J.2    Urbina, J.F.3
  • 4
    • 33646581697 scopus 로고    scopus 로고
    • Molecular tectonics: Generation of 1-and 2-D copper coordination networks by positional isomeric tectons based on a phenylenediamine backbone bearing two isonicotinoyl moieties
    • Pansanel, J.; Jouaiti, A.; Ferlay, S.; Hosseini, M. W.; Planeix, J.; Kyritsakas, N. Molecular tectonics: generation of 1-and 2-D copper coordination networks by positional isomeric tectons based on a phenylenediamine backbone bearing two isonicotinoyl moieties. New J. Chem. 2006, 30, 683.
    • (2006) New J. Chem , vol.30 , pp. 683
    • Pansanel, J.1    Jouaiti, A.2    Ferlay, S.3    Hosseini, M.W.4    Planeix, J.5    Kyritsakas, N.6
  • 5
    • 29744469024 scopus 로고    scopus 로고
    • Engineering crystals by the strategy of molecular tectonics
    • Wuest, J. D. Engineering crystals by the strategy of molecular tectonics. Chem. Commun. 2005, 5830.
    • (2005) Chem. Commun , pp. 5830
    • Wuest, J.D.1
  • 6
    • 5044235632 scopus 로고    scopus 로고
    • Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines?
    • Almarsson, Ö.; Zaworotko, M. J. Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines? Chem. Commun. 2004, 1889.
    • (2004) Chem. Commun , pp. 1889
    • Almarsson, O.1    Zaworotko, M.J.2
  • 9
    • 33846133535 scopus 로고    scopus 로고
    • Pharmaceutical cocrystal and salts of norfloxacin
    • Basavoju, S.; Bostroem, D.; Velaga, S. P. Pharmaceutical cocrystal and salts of norfloxacin. Cryst. Growth Des. 2006, 6, 2699.
    • (2006) Cryst. Growth Des , vol.6 , pp. 2699
    • Basavoju, S.1    Bostroem, D.2    Velaga, S.P.3
  • 10
    • 33746425242 scopus 로고    scopus 로고
    • Physical stability enhancement of theophylline via cocrystallization
    • Trask, A. V.; Motherwell, S. W. D.; Jones, W. Physical stability enhancement of theophylline via cocrystallization. Int. J. Pharm. 2006, 320, 114.
    • (2006) Int. J. Pharm , vol.320 , pp. 114
    • Trask, A.V.1    Motherwell, S.W.D.2    Jones, W.3
  • 11
    • 33645036399 scopus 로고    scopus 로고
    • Carboxamide-pyridine N-oxide heterosynthon for crystal engineering and pharmaceutical cocrystals
    • Reddy, S. L; Babu, J. N.; Nangia, A. Carboxamide-pyridine N-oxide heterosynthon for crystal engineering and pharmaceutical cocrystals. Chem. Commun. 2006, 1369.
    • (2006) Chem. Commun , pp. 1369
    • Reddy, S.L.1    Babu, J.N.2    Nangia, A.3
  • 13
    • 25844449757 scopus 로고    scopus 로고
    • Building co-crystals with molecular sense and supramolecular sensibility
    • Aakeröy, C. B.; Salmon, D. J. Building co-crystals with molecular sense and supramolecular sensibility. CrystEngComm 2005, 7, 439.
    • (2005) CrystEngComm , vol.7 , pp. 439
    • Aakeröy, C.B.1    Salmon, D.J.2
  • 14
    • 25444484704 scopus 로고    scopus 로고
    • Three-Component Carboxylic Acid-Bipyridine Lattice Inclusion Host. Supramolecular Synthesis of Ternary Cocrystals
    • Bhogala, B. R.; Basavoju, S.; Nangia, A. Three-Component Carboxylic Acid-Bipyridine Lattice Inclusion Host. Supramolecular Synthesis of Ternary Cocrystals. Cryst. Growth Des. 2005, 5, 1683.
    • (2005) Cryst. Growth Des , vol.5 , pp. 1683
    • Bhogala, B.R.1    Basavoju, S.2    Nangia, A.3
  • 15
    • 27744518934 scopus 로고    scopus 로고
    • Achieving Polymorphic and Stoichiometric Diversity in Cocrystal Formation: Importance of Solid-State Grinding, Powder X-ray Structure Determination, and Seeding
    • Trask, A. V.; van de Streek, J.; Motherwell, S. W. D.; Jones, W. Achieving Polymorphic and Stoichiometric Diversity in Cocrystal Formation: Importance of Solid-State Grinding, Powder X-ray Structure Determination, and Seeding. Cryst. Growth. Des. 2005, 6, 2233.
    • (2005) Cryst. Growth. Des , vol.6 , pp. 2233
    • Trask, A.V.1    van de Streek, J.2    Motherwell, S.W.D.3    Jones, W.4
  • 16
    • 25844464824 scopus 로고    scopus 로고
    • Crystal engineering with hydrogen bonds and halogen bonds
    • Saha, B. K.; Nangia, A.; Jaskolski, M. Crystal engineering with hydrogen bonds and halogen bonds. CrystEngComm. 2005, 7, 355.
    • (2005) CrystEngComm , vol.7 , pp. 355
    • Saha, B.K.1    Nangia, A.2    Jaskolski, M.3
  • 18
    • 14644423439 scopus 로고    scopus 로고
    • Reflection on molecular tectonics
    • Hosseini, M. W. Reflection on molecular tectonics. CrystEngComm 2004, 6, 318.
    • (2004) CrystEngComm , vol.6 , pp. 318
    • Hosseini, M.W.1
  • 19
    • 0035984036 scopus 로고    scopus 로고
    • Desiraju, G. R. Hydrogen Bridges in Crystal Engineering: Interactions without Borders. Acc. Chem. Res. 2002, 35, 565.
    • Desiraju, G. R. Hydrogen Bridges in Crystal Engineering: Interactions without Borders. Acc. Chem. Res. 2002, 35, 565.
  • 20
    • 27744432914 scopus 로고    scopus 로고
    • 8-Fold Interpenetration and Concomitant Polymorphism in the 2:3 CoCrystal of Trimesic Acid and 1,2-Bis(4-pyridyl)ethane
    • Shattock, T. R.; Vishweshwar, P.; Wang, Z.; Zaworotko, M. J. 8-Fold Interpenetration and Concomitant Polymorphism in the 2:3 CoCrystal of Trimesic Acid and 1,2-Bis(4-pyridyl)ethane. Cryst. Growth. Des. 2005, 6, 2046.
    • (2005) Cryst. Growth. Des , vol.6 , pp. 2046
    • Shattock, T.R.1    Vishweshwar, P.2    Wang, Z.3    Zaworotko, M.J.4
  • 21
    • 33646384404 scopus 로고    scopus 로고
    • Aakeröy, C. B.; Desper, J.; Salmon, D. J.; Smith, M. M. Cyanophenyloximes: Reliable and Versatile Tools for Hydrogen-Bond Directed Supramolecular Synthesis of Cocrystals. Cryst. Growth Des. 2006, 4, 1033.
    • Aakeröy, C. B.; Desper, J.; Salmon, D. J.; Smith, M. M. Cyanophenyloximes: Reliable and Versatile Tools for Hydrogen-Bond Directed Supramolecular Synthesis of Cocrystals. Cryst. Growth Des. 2006, 4, 1033.
  • 22
    • 33746914762 scopus 로고    scopus 로고
    • Improving success rate of hydrogen-bond driven synthesis of co-crystals
    • Aakeröy, C. B.; Fasulo, M. E.; Desper, J. Improving success rate of hydrogen-bond driven synthesis of co-crystals, CrystEngComm. 2006, 8, 586.
    • (2006) CrystEngComm , vol.8 , pp. 586
    • Aakeröy, C.B.1    Fasulo, M.E.2    Desper, J.3
  • 23
    • 16244423669 scopus 로고    scopus 로고
    • This requirement may be deemed overly restrictive, but it does offer an important distinction between solvates and cocrystals. However, in some cases, notably in the elegant work by Boese and co-workers, using low-temperature crystallizations, they intentionally prepare cocrystals with a very clear focus and deliberate strategy see, e.g, Kirchner, M. T, Boese, R, Gehrke, A, Blaeser, D. Co-crystallization with acetylene. Part III. Molecular complexes with aromatic azacycles. CrystEngComm 2004, 6, 360
    • This requirement may be deemed overly restrictive, but it does offer an important distinction between solvates and cocrystals. However, in some cases, notably in the elegant work by Boese and co-workers, using low-temperature crystallizations, they intentionally prepare cocrystals with a very clear focus and deliberate strategy (see, e.g.: Kirchner, M. T.; Boese, R.; Gehrke, A.; Blaeser, D. Co-crystallization with acetylene. Part III. Molecular complexes with aromatic azacycles. CrystEngComm 2004, 6, 360).
  • 24
    • 33645039124 scopus 로고    scopus 로고
    • Balancing supramolecular reagents for reliable formation of co-crystals
    • Aakeröy, C. B.; Desper, J.; Scott, B. M. T. Balancing supramolecular reagents for reliable formation of co-crystals. Chem. Comm. 2006, 1445.
    • (2006) Chem. Comm , pp. 1445
    • Aakeröy, C.B.1    Desper, J.2    Scott, B.M.T.3
  • 25
    • 16244411299 scopus 로고    scopus 로고
    • Heteromeric intermolecular interactions as synthetic tools for the formation of binary co-crystals
    • Aakeroy, C. B.; Desper, J.; Helfrich, B. A. Heteromeric intermolecular interactions as synthetic tools for the formation of binary co-crystals. CrystEngComm 2004, 6, 19.
    • (2004) CrystEngComm , vol.6 , pp. 19
    • Aakeroy, C.B.1    Desper, J.2    Helfrich, B.A.3
  • 26
    • 17144420754 scopus 로고    scopus 로고
    • Toward High-Yielding Supramolecular Synthesis: Directed Assembly of Ditopic Imidazoles/Benzimidazoles and Dicarboxylic Acids into Cocrystals via Selective O-H...N Hydrogen Bonds
    • Aakeröy, C. B.; Desper, J.; Leonard, B.; Urbina, J. F. Toward High-Yielding Supramolecular Synthesis: Directed Assembly of Ditopic Imidazoles/Benzimidazoles and Dicarboxylic Acids into Cocrystals via Selective O-H...N Hydrogen Bonds. CrystEngComm 2005, 5, 865.
    • (2005) CrystEngComm , vol.5 , pp. 865
    • Aakeröy, C.B.1    Desper, J.2    Leonard, B.3    Urbina, J.F.4
  • 27
    • 27744484364 scopus 로고    scopus 로고
    • Saccharin Salts of Active Pharmaceutical Ingredients, Their Crystal Structures, and Increased Water Solubilities
    • Banerjee, R.; Bhatt, P. M.; Ravindra, N. V.; Desiraju, G. M. Saccharin Salts of Active Pharmaceutical Ingredients, Their Crystal Structures, and Increased Water Solubilities. Cryst. Growth Des. 2005, 6, 2299.
    • (2005) Cryst. Growth Des , vol.6 , pp. 2299
    • Banerjee, R.1    Bhatt, P.M.2    Ravindra, N.V.3    Desiraju, G.M.4
  • 28
    • 34250868412 scopus 로고    scopus 로고
    • Only crystal structures of organic compounds that were successfully solved and refined were included, and all such structures obtained for a specific time period were included in the analysis in an attempt to ensure that no bias was introduced in the selection process
    • Only crystal structures of organic compounds that were successfully solved and refined were included, and all such structures obtained for a specific time period were included in the analysis in an attempt to ensure that no bias was introduced in the selection process.
  • 29
    • 0031962394 scopus 로고    scopus 로고
    • The quasi-symmetric OHN and ODN bridges in the adducts of 3,5-dimethylpyridine with 3,5-dinitrobenzoic acid
    • Jerzykiewicz, L. B.; Malarski, Z.; Sobczyk, L.; Lis, T.; Grech, E. The quasi-symmetric OHN and ODN bridges in the adducts of 3,5-dimethylpyridine with 3,5-dinitrobenzoic acid. J. Mol. Struct. 1998, 440, 175.
    • (1998) J. Mol. Struct , vol.440 , pp. 175
    • Jerzykiewicz, L.B.1    Malarski, Z.2    Sobczyk, L.3    Lis, T.4    Grech, E.5
  • 30
    • 0031559456 scopus 로고    scopus 로고
    • Proton transfer and correlations between the C-O, O-H, N-H and O..N bond lengths in amine phenolates
    • Majerz, I.; Malarski, Z.; Sobczyk, L. Proton transfer and correlations between the C-O, O-H, N-H and O..N bond lengths in amine phenolates. Chem. Phys. Lett. 1997, 274, 361.
    • (1997) Chem. Phys. Lett , vol.274 , pp. 361
    • Majerz, I.1    Malarski, Z.2    Sobczyk, L.3
  • 31
    • 2542482793 scopus 로고    scopus 로고
    • Variable-temperature neutron diffraction studies of the short, strong N...O hydrogen bonds in the 1:2 co-crystal of benzene-1,2,4,5-tetracarboxylic acid and 4,4′-bipyridyl
    • Cowan, J. A.; Howard, K.; McIntyre, G. J.; Lo, S. M. F.; Williams, I. D. Variable-temperature neutron diffraction studies of the short, strong N...O hydrogen bonds in the 1:2 co-crystal of benzene-1,2,4,5-tetracarboxylic acid and 4,4′-bipyridyl. Acta Crystallogr. 2003, B59, 794.
    • (2003) Acta Crystallogr , vol.B59 , pp. 794
    • Cowan, J.A.1    Howard, K.2    McIntyre, G.J.3    Lo, S.M.F.4    Williams, I.D.5
  • 32
    • 34250879655 scopus 로고    scopus 로고
    • Crystallographic data for 1, 1, pyrazol-1-yl)methyl],4, benzimidazol-1-yl)methyl]benzene, succinic acid (2:1, C40H 38N8O4, M, 694.78 amu, monoclinic, space group P2(1)/n, a, 5.6367(4) Å, b, 32.910(3) Å, c, 9.4476(7) Å, α, 90°, β, 102.342(6)°, γ, 90°, V, 1712.0(2) Å3, Z, 2, Dc, 1.348 g/cm3, μ(Mo Kα, 0.090 mm-1, crystal size 0.45 x 0.40 x 0.04 mm3. Data were collected at 173 K on a Bruker SMART 1000 diffractometer using Mo Kα radiation. A total of 12611 reflections (1.24° < θ < 28.32°) were processed of which 4018 were unique and significant with I > 2σI, Structure solution and refinement were carried out with the SHELXL-9714 software package release 97-2. Final residuals for I > 2
    • 2 = 0.1276 (GOF = 0.920).
  • 33
    • 34250810804 scopus 로고    scopus 로고
    • Crystallographic data for 2, 3-(4-pyridyl)pyrazole, 2,6-difluorobenzoic acid (1:1, C15H11F2N 3O2, M, 303.27 amu, monoclinic, space group P2(1)/n, a, 7.1555(8) Å, b, 17.958(2) Å, c, 10.9686(12) Å, α, 90°, β, 101.301(2)°, γ, 90°, V, 1382.1(3) Å3, Z, 4, Dc, 1.457 g/cm3, μ(Mo Kα, 0.118 mm -1, crystal size 0.46 x 0.16 x 0.07 mm3. Data were collected at 203 K on a Bruker SMART 1000 diffractometer using Mo Kα radiation. A total of 5396 reflections (2.21° < θ < 28.24°) were processed of which 3167 were unique and significant with I > 2σ(I, Structure solution and refinement were carried out with the SHELXL-9714 software package release 97-2. Final residuals for I > 2σ(I) were R
    • 2 = 0.1056 (GOF = 1.050).
  • 34
    • 34250895005 scopus 로고    scopus 로고
    • Crystallographic data for 3, 3-(4-pyridinium)pyrazole pentamethylbenzoate pentamethylbenzoic acid (1:1:1, C32H 39N3O4, M, 529.66 amu, triclinic, space group P1, a, 8.8864(5) Å, b, 11.9875(7) Å, c, 13.7015(8) Å, α, 99.3800(10)°, β, 93.1910(10)°, γ, 107.5560(10)°, V, 1364.42(14) Å3, Z, 2, Dc, 1.289 g/cm 3, μ(Mo Kα, 0.085 mm-1, crystal size 0.09 x 0.24 x 0.36 mm3. Data were collected at 100 K on a Bruker SMART 1000 diffractometer using Mo Kα radiation. A total of 16736 reflections (2.53° < θ < 30.53°) were processed of which 8185 were unique and significant with I > 2σI, Structure solution and refinement were carried out with the SHELXL-9714 software package release 97-2. Final residuals for
    • 2 = 0.1240 (GOF = 0.947).
  • 35
    • 34250882168 scopus 로고    scopus 로고
    • Crystallographic data for 4, 1, pyrazol-1-yl)methyl, 3, benzimidazol-1-yl)methyl]benzene, 3,5-dinitrobenzoate, 3,5-dinitrobenzoic acid (1:1:1, C32H24N8O12, M, 712.59 amu, triclinic, space group P1, a, 9.7657(6) Å, b, 11.7691(7) Å, c, 14.0803(9) Å, α, 86.2270(10)°, β, 74.1630(10)°, γ, 86.2020(10)°, V, 1551.53(17) Å3, Z, 2, Dc, 1.525 g/cm3, μ(Mo Kα, 0.120 mm-1, crystal size 0.46 x 0.36 x 0.28 mm3. Data were collected at 100 K on a Broker SMART 1000 diffractometer using Mo Kα radiation. A total of 12611 reflections (2.24° < θ < 30.08°) were processed of which 4018 were unique and significant with I > 2σI, Structure solution and refinement were carried out with the SHELXL-97 14 software packag
    • 2 = 0.1240 (GOF = 1.024).
  • 36
    • 0033549581 scopus 로고    scopus 로고
    • Molecular beside ionic: Crystal structures of a 1/1 and a 1/4 adduct of pyridine and formic acid
    • Wiechert, D.; Mootz, D. Molecular beside ionic: crystal structures of a 1/1 and a 1/4 adduct of pyridine and formic acid. Angew. Chem., Int. Ed. 1999, 38, 1974.
    • (1999) Angew. Chem., Int. Ed , vol.38 , pp. 1974
    • Wiechert, D.1    Mootz, D.2
  • 37
    • 15744376252 scopus 로고    scopus 로고
    • Electron and Nuclear Positions in the Short Hydrogen Bond in Urotropine-N-oxide Formic Acid
    • Nygren, C. L.; Wilson, C. C.; Turner, J. F. C. Electron and Nuclear Positions in the Short Hydrogen Bond in Urotropine-N-oxide Formic Acid. J. Phys. Chem. A 2005, 109, 1911.
    • (2005) J. Phys. Chem. A , vol.109 , pp. 1911
    • Nygren, C.L.1    Wilson, C.C.2    Turner, J.F.C.3
  • 38
    • 0001752768 scopus 로고    scopus 로고
    • The Cambridge Structural Database: A quarter of a million crystal structures and rising
    • Allen, F. A.; The Cambridge Structural Database: a quarter of a million crystal structures and rising, Acta Crystallogr. B 2002, 58, 380.
    • (2002) Acta Crystallogr. B , vol.58 , pp. 380
    • Allen, F.A.1


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