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Volumn 55, Issue 7, 2012, Pages 1228-1235

Hydrogen-bonding directed cocrystallization of flexible piperazine with hydroxybenzoic acid derivatives: Structural diversity and synthon prediction

Author keywords

Crystal engineering; Hydroxybenzoic acid; Piperazine; Supramolecular synthons

Indexed keywords

BUILDING BLOCKES; CHAIR CONFORMATIONS; COCRYSTALLIZATION; DICATIONS; DIRECTED ASSEMBLY; HYDROXYBENZOIC ACIDS; PIPERAZINE; PROTONATED; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS; STRUCTURAL DIVERSITY; SUPRAMOLECULAR SYNTHONS; SYNTHONS;

EID: 84866136818     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-011-4487-4     Document Type: Article
Times cited : (13)

References (32)
  • 1
    • 0344096487 scopus 로고
    • Crystal engineering: New concepts in crystallography
    • Pepinsky R. Crystal engineering: New concepts in crystallography. Phys Rev, 1955, 100: 971-971
    • (1955) Phys Rev , vol.100 , pp. 971-971
    • Pepinsky, R.1
  • 2
    • 84943076505 scopus 로고
    • Photodimerization in the solid state
    • Schmidt GM. Photodimerization in the solid state. J Pure Appl Chem, 1971, 27: 647-678
    • (1971) J Pure Appl Chem , vol.27 , pp. 647-678
    • Schmidt, G.M.1
  • 3
    • 0344099416 scopus 로고    scopus 로고
    • Crystal engineering where from? Where to?
    • (a) Braga D. Crystal engineering, Where from? Where to? Chem Commun, 2003, 2751-2754;
    • (2003) Chem Commun , pp. 2751-2754
    • Braga, D.1
  • 5
    • 33748530600 scopus 로고    scopus 로고
    • Synthon robustness in saccharinate salts of some substituted pyridines
    • (c) Banerjee R, Saha BK, Desiraju GR. Synthon robustness in saccharinate salts of some substituted pyridines. CrystEngComm, 2006, 8: 680-685
    • (2006) CrystEngComm , vol.8 , pp. 680-685
    • Banerjee, R.1    Saha, B.K.2    Desiraju, G.R.3
  • 6
    • 33645459483 scopus 로고    scopus 로고
    • Molecular Building Blocks Approach to the Assembly of Zeolite-like Metal-organic Frameworks (ZMOFs) with Extra-large Cavities
    • (a) Liu YL, Kravtsov VC, Larsen R, Eddaoudi M. Molecular building blocks approach to the assembly of zeolite-like metal-organic frameworks (ZMOFs) with extra-large cavities. Chem Commun, 2006, 1488-1490;
    • (2006) Chem Commun , pp. 1488-1490
    • Liu, Y.L.1    Kravtsov, V.C.2    Larsen, R.3    Eddaoudi, M.4
  • 7
    • 25444507730 scopus 로고    scopus 로고
    • A chromium terephthalate-based solid with unusually large pore volumes and surface area
    • (b) Ferey G, Mellot DC, Serre C, Millange F, Dutour J, Surble S, Margiolaki I. A chromium terephthalate-based solid with unusually large pore volumes and surface area. Science, 2005, 309: 2040-2042
    • (2005) Science , vol.309 , pp. 2040-2042
    • Ferey, G.1    Mellot, D.C.2    Serre, C.3    Millange, F.4    Dutour, J.5    Surble, S.6    Margiolaki, I.7
  • 8
    • 78651105022 scopus 로고    scopus 로고
    • Pharmaceutical co-crystals with isonicotinamide-vitamin B3, clofibric acid, and diclofenac- and two isonicotinamide hydrates
    • (a) Báthori NB, Lemmerer A, Venter GA, Bourne SA, Caira MR. Pharmaceutical co-crystals with isonicotinamide-vitamin B3, clofibric acid, and diclofenac- and two isonicotinamide hydrates. Cryst Growth Des, 2011, 11: 75-87;
    • (2011) Cryst Growth des , vol.11 , pp. 75-87
    • Báthori, N.B.1    Lemmerer, A.2    Venter, G.A.3    Bourne, S.A.4    Caira, M.R.5
  • 9
    • 4544273857 scopus 로고    scopus 로고
    • Is melt crystallization a green technology?
    • (b) Ulrich J. Is melt crystallization a green technology? Cryst Growth Des, 2004, 4: 879-880
    • (2004) Cryst Growth des , vol.4 , pp. 879-880
    • Ulrich, J.1
  • 10
    • 16244404244 scopus 로고    scopus 로고
    • The influence of the trimethylsilyl group: Helical self-assembly of syn-7-trimethylsilyl-5-norbornene- endo-2,3-dicarboxylic acid
    • Begum NS, Girjia CR, Nagendrappa G. The influence of the trimethylsilyl group: Helical self-assembly of syn-7-trimethylsilyl-5-norbornene- endo-2,3-dicarboxylic acid. CrystEngComm, 2004, 6: 116-119
    • (2004) CrystEngComm , vol.6 , pp. 116-119
    • Begum, N.S.1    Girjia, C.R.2    Nagendrappa, G.3
  • 11
    • 16244404253 scopus 로고    scopus 로고
    • The co-crystallisation of pyridine with benzenepolycarboxylic acids: The interplay of strong and weak hydrogen bonding motifs
    • Dale SH, Elsegood MRJ, Hemmings M, Wilkinson AL. The co-crystallisation of pyridine with benzenepolycarboxylic acids: The interplay of strong and weak hydrogen bonding motifs. CrystEngComm, 2004, 6: 207-214
    • (2004) CrystEngComm , vol.6 , pp. 207-214
    • Dale, S.H.1    Elsegood, M.R.J.2    Hemmings, M.3    Wilkinson, A.L.4
  • 12
    • 79953860696 scopus 로고    scopus 로고
    • Recent developments in crystal engineering
    • Biradha K, Su CY, Vittal JJ. Recent developments in crystal engineering. Cryst Growth Des, 2011, 11: 875-886;
    • (2011) Cryst Growth des , vol.11 , pp. 875-886
    • Biradha, K.1    Su, C.Y.2    Vittal, J.J.3
  • 13
    • 54949083828 scopus 로고    scopus 로고
    • Robust supramolecular heterosynthons in chiral ammonium carboxylate salts
    • (b) Lemmerer A, Bourne SA, Fernandes MA. Robust supramolecular heterosynthons in chiral ammonium carboxylate salts. Cryst Growth Des, 2008, 8: 1106-1109
    • (2008) Cryst Growth des , vol.8 , pp. 1106-1109
    • Lemmerer, A.1    Bourne, S.A.2    Fernandes, M.A.3
  • 14
    • 77957704751 scopus 로고    scopus 로고
    • Carboxylic acid and phenolic hydroxyl interactions in the crystal structures of co-crystals/clathrates of trimesic acid and pyromellitic acid with phenolic derivatives
    • Rajput L, Jana N, Biradha K. Carboxylic acid and phenolic hydroxyl interactions in the crystal structures of co-crystals/clathrates of trimesic acid and pyromellitic acid with phenolic derivatives. Cryst Growth Des, 2010, 10: 4565-4570;
    • (2010) Cryst Growth des , vol.10 , pp. 4565-4570
    • Rajput, L.1    Jana, N.2    Biradha, K.3
  • 15
    • 31144447353 scopus 로고    scopus 로고
    • Hydrogen bonding in crystal structures of N,N'-bis(3-pyridyl)urea. Why is the N-H...O tape synthon absent in diaryl ureas with electron-withdrawing groups?
    • (b) Reddy LS, Basnati G, Vangala VR, Nangia A. Hydrogen bonding in crystal structures of N,N'-bis(3-pyridyl)urea. Why is the N-H...O tape synthon absent in diaryl ureas with electron-withdrawing groups? Cryst Growth Des, 2006, 6: 161-173
    • (2006) Cryst Growth des , vol.6 , pp. 161-173
    • Reddy, L.S.1    Basnati, G.2    Vangala, V.R.3    Nangia, A.4
  • 16
    • 33646378664 scopus 로고    scopus 로고
    • Synthon robustness and solid- state architecture in substituted gem-alkynols
    • Banerjee R, Saha BK, Desiraju GR. Synthon robustness and solid- state architecture in substituted gem-alkynols. Cryst Growth Des, 2006, 6: 999-1009
    • (2006) Cryst Growth des , vol.6 , pp. 999-1009
    • Banerjee, R.1    Saha, B.K.2    Desiraju, G.R.3
  • 17
    • 0001475723 scopus 로고
    • Molecular packing modes: Carboxylic acids
    • Leiserowitz L. Molecular packing modes: Carboxylic acids. Acta Cyrstallogr Sect B, 1976, 32: 775-802
    • (1976) Acta Cyrstallogr Sect B , vol.32 , pp. 775-802
    • Leiserowitz, L.1
  • 18
    • 18044392054 scopus 로고    scopus 로고
    • Elguero, Supramolecular structure of 1H-pyrazoles in the solid state: A crystallographic and ab initio study
    • Foces FC, Alkorta I, Elguero, Supramolecular structure of 1H-pyrazoles in the solid state: A crystallographic and ab initio study. Acta Crystallogr, Sect B, 2000, 56: 1018-1028
    • (2000) Acta Crystallogr, Sect B , vol.56 , pp. 1018-1028
    • Foces, F.C.1    Alkorta, I.2
  • 19
    • 31144434845 scopus 로고    scopus 로고
    • Synthons competition/ prediction in cocrystallization of flexible dicarboxylic acids with bent dipyridines
    • (a) Du M, Zhang ZH, Zhao XJ, Cai H. Synthons competition/ prediction in cocrystallization of flexible dicarboxylic acids with bent dipyridines. Cryst Growth Des, 2006, 6: 114-121;
    • (2006) Cryst Growth des , vol.6 , pp. 114-121
    • Du, M.1    Zhang, Z.H.2    Zhao, X.J.3    Cai, H.4
  • 20
    • 34347242852 scopus 로고    scopus 로고
    • Cocrystals of 3,5-dimethyl-1H-pyrazole and salicylic acid: Controlled formation of trimers via O-H...N hydrogen bonds
    • (b) López C, Claramunt RM, Garcia MA, Pinilla E, Terres MR, Alkorta I, Elguero J. Cocrystals of 3,5-dimethyl-1H-pyrazole and salicylic acid: Controlled formation of trimers via O-H...N hydrogen bonds. Cryst Growth Des, 2007, 7: 1176-1184
    • (2007) Cryst Growth des , vol.7 , pp. 1176-1184
    • López, C.1    Claramunt, R.M.2    Garcia, M.A.3    Pinilla, E.4    Terres, M.R.5    Alkorta, I.6    Elguero, J.7
  • 21
    • 8844275016 scopus 로고    scopus 로고
    • Crystal and co-crystal
    • Desiraju GR, Crystal and co-crystal. CrystEngComm, 2003, 5: 466-467
    • (2003) CrystEngComm , vol.5 , pp. 466-467
    • Desiraju, G.R.1
  • 22
    • 25844449757 scopus 로고    scopus 로고
    • Building co-crystals with molecular sense and supramolecular sensibility
    • Aakeröy CB, Salmon DJ. Building co-crystals with molecular sense and supramolecular sensibility. CrystEngComm, 2005, 7: 439-448
    • (2005) CrystEngComm , vol.7 , pp. 439-448
    • Aakeröy, C.B.1    Salmon, D.J.2
  • 23
    • 65249147115 scopus 로고    scopus 로고
    • Multi-component hydrogenbonding assembly of a pharmaceutical agent pamoic acid with piperazine or 4,4'-bipyridyl: A channel hydrated salt with multiple-helical motifs vs a bimolecular cocrystal
    • Du M, Zhang ZH, Guo W, Fu XJ. Multi-component hydrogenbonding assembly of a pharmaceutical agent pamoic acid with piperazine or 4,4'-bipyridyl: A channel hydrated salt with multiple-helical motifs vs a bimolecular cocrystal. Cryst Growth Des, 2009, 9: 1655-1657
    • (2009) Cryst Growth des , vol.9 , pp. 1655-1657
    • Du, M.1    Zhang, Z.H.2    Guo, W.3    Fu, X.J.4
  • 24
    • 33748259777 scopus 로고    scopus 로고
    • Flexible building blocks of N,N'-bis(picolinoyl)hydrazine for hydrogen-bonding directed cocrystallization: Structural diversity, concomitant polymorphs, and synthon prediction
    • Du M, Zhang ZH, Wang XG, Wu HF, Wang Q. Flexible building blocks of N,N'-bis(picolinoyl)hydrazine for hydrogen-bonding directed cocrystallization: Structural diversity, concomitant polymorphs, and synthon prediction. Cryst Growth Des, 2006, 6: 1867-1875
    • (2006) Cryst Growth des , vol.6 , pp. 1867-1875
    • Du, M.1    Zhang, Z.H.2    Wang, X.G.3    Wu, H.F.4    Wang, Q.5
  • 25
    • 32644436467 scopus 로고    scopus 로고
    • A search for predictable hydrogenbonding synthons in cocrystallization of unusual organic acids with a bent dipyridine
    • Du M, Zhang ZH, Zhao XJ. A search for predictable hydrogenbonding synthons in cocrystallization of unusual organic acids with a bent dipyridine. Cryst Growth Des, 2006, 6: 390-396
    • (2006) Cryst Growth des , vol.6 , pp. 390-396
    • Du, M.1    Zhang, Z.H.2    Zhao, X.J.3
  • 26
    • 75249101061 scopus 로고    scopus 로고
    • Crystal forms of the antibiotic 4-aminosalicylic acid: Solvates and molecular salts with dioxane, morpholine, and piperazine
    • (a) Andre V, Braga D, Grepioni F, Duarte MT. Crystal forms of the antibiotic 4-aminosalicylic acid: Solvates and molecular salts with dioxane, morpholine, and piperazine. Cryst Growth Des, 2009, 9: 5108-5116;
    • (2009) Cryst Growth des , vol.9 , pp. 5108-5116
    • Andre, V.1    Braga, D.2    Grepioni, F.3    Duarte, M.T.4
  • 27
    • 60849133638 scopus 로고    scopus 로고
    • Mechanochemistry and cocrystals
    • (b) Skovsgaard S, Bond AD. Mechanochemistry and cocrystals. CrystEngComm, 2009, 11: 444-453
    • (2009) CrystEngComm , vol.11 , pp. 444-453
    • Skovsgaard, S.1    Bond, A.D.2
  • 30
    • 77951848630 scopus 로고    scopus 로고
    • Crystal engineered acid-base complexes with 2D and 3D hydrogen bonding systems using p-hydroxybenzoic acid as the building block
    • Zhao PS, Wang X, Jian FF, Zhang JL, Xiao HL. Crystal engineered acid-base complexes with 2D and 3D hydrogen bonding systems using p-hydroxybenzoic acid as the building block. J Serb Chem Soc, 2010, 75: 459-473
    • (2010) J Serb Chem Soc , vol.75 , pp. 459-473
    • Zhao, P.S.1    Wang, X.2    Jian, F.F.3    Zhang, J.L.4    Xiao, H.L.5
  • 31
    • 0000116254 scopus 로고    scopus 로고
    • Hydrated salts of 3,5-dihydroxybenzoic acid with organic diamines: Hydrogen- bonded supramolecular structures in two and three dimensions. Acta Cyrstallogr
    • Burchell CJ, Ferguson G, Lough AJ, Gregson RM, Glidewell C. Hydrated salts of 3,5-dihydroxybenzoic acid with organic diamines: hydrogen- bonded supramolecular structures in two and three dimensions. Acta Cyrstallogr, Sect B, 2001, 57: 329-338
    • (2001) Sect B , vol.57 , pp. 329-338
    • Burchell, C.J.1    Ferguson, G.2    Lough, A.J.3    Gregson, R.M.4    Glidewell, C.5
  • 32
    • 60849133638 scopus 로고    scopus 로고
    • Co-crystallisation of benzoic acid derivatives with N-containing bases in solution and by mechanical grinding: Stoichiometric variants, polymorphism and twinning
    • Skovsgaard S, Bond AD. Co-crystallisation of benzoic acid derivatives with N-containing bases in solution and by mechanical grinding: Stoichiometric variants, polymorphism and twinning. CrystEngComm, 2009, 11: 444-453
    • (2009) CrystEngComm , vol.11 , pp. 444-453
    • Skovsgaard, S.1    Bond, A.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.