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Volumn 370, Issue 1969, 2012, Pages 2900-2915

Unusual co-crystal of isonicotinamide: The structural landscape in crystal engineering

Author keywords

Crystal engineering; Crystallization; Hydrogen bond

Indexed keywords

AMIDES; CRYSTAL ENGINEERING; CRYSTALLIZATION; HYDROGEN BONDS;

EID: 84861954527     PISSN: 1364503X     EISSN: None     Source Type: Journal    
DOI: 10.1098/rsta.2011.0309     Document Type: Review
Times cited : (46)

References (38)
  • 1
    • 36148966165 scopus 로고    scopus 로고
    • Crystal engineering: A holistic view
    • DOI 10.1002/anie.200700534
    • Desiraju, G. R. 2007 Crystal engineering: a holistic view. Angew. Chem. Int. Ed. 46, 8342-8356. (doi:10.1002/anie.200700534) (Pubitemid 350114938)
    • (2007) Angewandte Chemie - International Edition , vol.46 , Issue.44 , pp. 8342-8356
    • Desiraju, G.R.1
  • 2
    • 0036169222 scopus 로고    scopus 로고
    • The chemistry of intermolecular bonding: Organic crystals, their structures and transformations
    • Gavezzotti, A. 2002 The chemistry of intermolecular bonding: organic crystals, their structures and transformations. Synlett 2, 201-214. (doi:10.1055/s-2002-19742) (Pubitemid 34132706)
    • (2002) Synlett , Issue.2 , pp. 201-214
    • Gavezzotti, A.1
  • 3
    • 84949998029 scopus 로고    scopus 로고
    • The supramolecular synthon in crystal engineering
    • (eds F. Vögtle, J. F. Stoddart & M. Shibasaki), Weinheim, Germany: Wiley-VCH.
    • Desiraju, G. R. 2000 The supramolecular synthon in crystal engineering. In Stimulating concepts in chemistry (eds F. Vögtle, J. F. Stoddart & M. Shibasaki), pp. 293-306. Weinheim, Germany: Wiley-VCH.
    • (2000) Stimulating Concepts in Chemistry , pp. 293-306
    • Desiraju, G.R.1
  • 4
    • 0344152356 scopus 로고    scopus 로고
    • Polymorph Selection: Challenges for the Future?
    • DOI 10.1021/cg030025k
    • Blagden, N. & Davey, R. J. 2003 Polymorph selection: challenges for the future? Cryst. Growth Des. 3, 873-885. (doi:10.1021/cg030025k) (Pubitemid 37467738)
    • (2003) Crystal Growth and Design , vol.3 , Issue.6 , pp. 873-885
    • Blagden, N.1    Davey, R.J.2
  • 6
    • 33748352372 scopus 로고    scopus 로고
    • Concerning the relationship between structural and growth synthons in crystal nucleation: Solution and crystal chemistry of carboxylic acids as revealed through IR spectroscopy
    • DOI 10.1021/cg060058a
    • Davey, R. J., Dent, G., Mughal, R. K. & Parveen, S. 2006 Concerning the relationship between structural and growth synthons in crystal nucleation: solution and crystal chemistry of carboxylic acids as revealed through IR spectroscopy. Cryst. Growth Des. 6, 1788-1796. (doi:10.1021/cg060058a) (Pubitemid 44334950)
    • (2006) Crystal Growth and Design , vol.6 , Issue.8 , pp. 1788-1796
    • Davey, R.J.1    Dent, G.2    Mughal, R.K.3    Parveen, S.4
  • 7
    • 79955161581 scopus 로고    scopus 로고
    • Can a computer crystallize a liquid? Molecular simulation of continuous trajectories from liquid to crystalline n-hexane
    • (doi:10.1039/C1CE05106G)
    • Gavezzotti, A. 2011 Can a computer crystallize a liquid? Molecular simulation of continuous trajectories from liquid to crystalline n-hexane. CystEngComm 13, 3573-3579. (doi:10.1039/C1CE05106G)
    • (2011) CystEngComm , vol.13 , pp. 3573-3579
    • Gavezzotti, A.1
  • 10
    • 79957979325 scopus 로고    scopus 로고
    • Polymorphs, pseudopolymorphs, and co-crystals of orcinol: Exploring the structural landscape with high throughput crystallography
    • (doi:10.1021/cg200361x)
    • Mukherjee, A., Grobelny, P., Thakur, T. S. & Desiraju, G. R. 2011 Polymorphs, pseudopolymorphs, and co-crystals of orcinol: exploring the structural landscape with high throughput crystallography. Cryst. Growth Des. 11, 2637-2653. (doi:10.1021/cg200361x)
    • (2011) Cryst. Growth Des. , vol.11 , pp. 2637-2653
    • Mukherjee, A.1    Grobelny, P.2    Thakur, T.S.3    Desiraju, G.R.4
  • 11
    • 0037266029 scopus 로고    scopus 로고
    • Do polymorphic compounds make good cocrystallizing agents? A structural case study that demonstrates the importance of synthon flexibility
    • DOI 10.1021/cg025593z
    • Aakeröy, C. B., Beatty, A. M., Helfrich, B. A. & Nieuwenhuyzen, M. 2003 Do polymorphic compounds make good cocrystallizing agents? A structural case study that demonstrates the importance of synthon flexibility. Cryst. Growth Des. 3, 159-165. (doi:10.1021/cg025593z) (Pubitemid 37130600)
    • (2003) Crystal Growth and Design , vol.3 , Issue.2 , pp. 159-165
    • Aakeroy, C.B.1    Beatty, A.M.2    Helfrich, B.A.3    Nieuwenhuyzen, M.4
  • 12
    • 16244411299 scopus 로고    scopus 로고
    • Heteromeric intermolecular interactions as synthetic tools for the formation of binary co-crystals
    • DOI 10.1039/b315181f, 5
    • Aakeröy, C. B., Desper, J. & Helfrich, B. A. 2004 Heteromeric intermolecular interactions as synthetic tools for the formation of binary co-crystals. CystEngComm 6, 19-24. (doi:10.1039/B315181F) (Pubitemid 40464517)
    • (2004) CrystEngComm , vol.6 , pp. 19-24
    • Aakeroy, C.B.1    Desper, J.2    Helfrich, B.A.3
  • 13
    • 35349020620 scopus 로고    scopus 로고
    • Combining halogen bonds and hydrogen bonds in the modular assembly of heteromeric infinite 1-D chains
    • DOI 10.1039/b707458a
    • Aakeröy, C. B., Desper, J., Helfrich, B. A., Metrangolo, P., Pilati, T., Resnati, G. & Stevenazzi, A. 2007 Combining halogen bonds and hydrogen bonds in the modular assembly of heteromeric infinite 1-D chains. Chem. Commun. 4236-4238. (doi:10.1039/b707458a) (Pubitemid 47598748)
    • (2007) Chemical Communications , Issue.41 , pp. 4236-4238
    • Aakeroy, C.B.1    Desper, J.2    Helfrich, B.A.3    Metrangolo, P.4    Pilati, T.5    Resnati, G.6    Stevenazzi, A.7
  • 14
    • 78751520942 scopus 로고    scopus 로고
    • New polymorphs of isonicotinamide and nicotinamide
    • (doi:10.1039/c0cc04117c)
    • Li, S., Bourne, A. & Caira, M. R. 2011 New polymorphs of isonicotinamide and nicotinamide. Chem. Commun. 47, 1530-1532. (doi:10.1039/c0cc04117c)
    • (2011) Chem. Commun. , vol.47 , pp. 1530-1532
    • Li, S.1    Bourne, A.2    Caira, M.R.3
  • 15
    • 61649100126 scopus 로고    scopus 로고
    • Controlling the formation of benzoic acid: Isonicotinamide molecular complexes
    • (doi:10.1021/ cg701024c)
    • Seaton, C. C., Parkin, A., Wilson, C. C. & Blagden, N. 2009 Controlling the formation of benzoic acid: isonicotinamide molecular complexes. Cryst. Growth Des. 9, 47-56. (doi:10.1021/ cg701024c)
    • (2009) Cryst. Growth Des. , vol.9 , pp. 47-56
    • Seaton, C.C.1    Parkin, A.2    Wilson, C.C.3    Blagden, N.4
  • 16
    • 1642459194 scopus 로고    scopus 로고
    • Supramolecular synthons in phenol-isonicotinamide adducts
    • DOI 10.1039/b304078j, 31
    • Vishweshwar, P., Nangia, A. & Lynch, V. M. 2003 Supramolecular synthons in phenol- isonicotinamide adducts. CystEngComm 5, 164-168. (doi:10.1039/B304078J) (Pubitemid 40447045)
    • (2003) CrystEngComm , vol.5 , pp. 164-168
    • Vishweshwar, P.1    Nangia, A.2    Lynch, V.M.3
  • 17
    • 1642567963 scopus 로고    scopus 로고
    • 4 network and the first example of (pyridine)N-Ag-O(amide) bonds
    • DOI 10.1021/cg034157p
    • Bhogala, B. R., Thallapally, P. K. & Nangia, A. 2004 1:2 and 1:1 Ag(I)-isonicotinamide coordination compounds: five-fold interpenetrated CdSO4 network and the first example of (pyridine)N-Ag-O(amide) bonds. Cryst. Growth Des. 4, 215-218. (doi:10.1021/cg034157p) (Pubitemid 38406229)
    • (2004) Crystal Growth and Design , vol.4 , Issue.2 , pp. 215-218
    • Bhogala, B.R.1    Thallapally, P.K.2    Nangia, A.3
  • 18
    • 25844524863 scopus 로고    scopus 로고
    • Tape and layer structures in cocrystals of some di- and tricarboxylic acids with 4,4-bipyridines and isonicotinamide. From binary to ternary cocrystals
    • DOI 10.1039/b509162d
    • Bhogala, B. R., Basavoju, S. & Nangia, A. 2005 Tape and layer structures in cocrystals of some di- and tricarboxylic acids with 4,4-bipyridines and isonicotinamide. From binary to ternary cocrystals. CystEngComm 7, 551-562. (doi:10.1039/B509162D) (Pubitemid 41396850)
    • (2005) CrystEngComm , vol.7 , pp. 551-562
    • Bhogala, B.R.1    Basavoju, S.2    Nangia, A.3
  • 19
    • 33745394944 scopus 로고
    • Supramolecular synthons in crystal engineering: A new organic synthesis
    • (doi:10.1002/anie.199523111)
    • Desiraju, G. R. 1995 Supramolecular synthons in crystal engineering: a new organic synthesis. Angew. Chem. Int. Ed. Engl. 34, 2311-2327. (doi:10.1002/anie.199523111)
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2311-2327
    • Desiraju, G.R.1
  • 20
    • 0006589268 scopus 로고
    • Encoding and decoding hydrogen-bond patterns of organic compounds
    • (doi:10.1021/ar00172a005)
    • Etter, M. C. 1990 Encoding and decoding hydrogen-bond patterns of organic compounds. Acc. Chem. Res. 23, 120-126. (doi:10.1021/ar00172a005)
    • (1990) Acc. Chem. Res. , vol.23 , pp. 120-126
    • Etter, M.C.1
  • 22
    • 0141627908 scopus 로고    scopus 로고
    • Molecular complexes of homologous alkanedicarboxylic acids with isonicotinamide: X-ray crystal structures, hydrogen bond synthons, and melting point alternation
    • DOI 10.1021/cg034037h
    • Vishweshwar, P., Nangia, A. & Lynch, V. M. 2003 Molecular complexes of homologous alkanedicarboxylic acids with isonicotinamide: X-ray crystal structures, hydrogen bond synthons, and melting point alternation. Cryst. Growth Des. 3, 783-790. (doi:10.1021/ cg034037h) (Pubitemid 37162291)
    • (2003) Crystal Growth and Design , vol.3 , Issue.5 , pp. 783-790
    • Vishweshwar, P.1    Nangia, A.2    Lynch, V.M.3
  • 23
    • 79958002338 scopus 로고    scopus 로고
    • The crystal structures and melting point properties of isonicotinamide cocrystals with alkanediacids HO2C(CH2)n-2CO2H n =7-9
    • (doi:10.1039/C1CE05160A)
    • Thompson, L. J., Voguri, R. S., Male, L. & Tremayne, M. 2011 The crystal structures and melting point properties of isonicotinamide cocrystals with alkanediacids HO2C(CH2)n-2CO2H n =7-9. CystEngComm 13, 4188-4195. (doi:10.1039/C1CE05160A)
    • (2011) CystEngComm , vol.13 , pp. 4188-4195
    • Thompson, L.J.1    Voguri, R.S.2    Male, L.3    Tremayne, M.4
  • 24
    • 0035801532 scopus 로고    scopus 로고
    • "Total synthesis" supramolecular style: Design and hydrogen-bond-directed assembly of ternary supermolecules
    • DOI 10.1002/1521-3773(20010903)40:17<3240::AID-ANIE3240>3.0.CO;2-X
    • Aakeröy, C. B., Beatty, A. M. & Helfrich, B. A. 2001 'Total synthesis' supramolecular style: design and hydrogen-bond-directed assembly of ternary supermolecules. Angew. Chem. Int. Ed. 40, 3240-3242. (doi:10.1002/1521-3773(20010903)40:17<3240::AID-ANIE3240> 3.0.CO;2-X) (Pubitemid 32845406)
    • (2001) Angewandte Chemie - International Edition , vol.40 , Issue.17 , pp. 3240-3242
    • Aakery, C.B.1    Beatty, A.M.2    Helfrich, B.A.3
  • 25
    • 32644445573 scopus 로고    scopus 로고
    • The importance of weak C-H·O bonds and · stacking interactions in the formation of organic 1,8-bis(dimethylamino)naphthalene complexes with Z′ > 1
    • DOI 10.1021/cg0503806
    • Nichol, G. S. & Clegg, W. 2006 The importance of weak C-H· · ·O bonds and π · · · π stacking interactions in the formation of organic 1,8-bis(dimethylamino)naphthalene complexes with Z′ >1. Cryst. Growth Des. 6, 451-460. (doi:10.1021/cg0503806) (Pubitemid 43242106)
    • (2006) Crystal Growth and Design , vol.6 , Issue.2 , pp. 451-460
    • Nichol, G.S.1    Clegg, W.2
  • 26
    • 0000698294 scopus 로고    scopus 로고
    • Structure predictions allowing more than one molecule in the asymmetric unit
    • (doi:10.1107/S0108768100000276)
    • van Eijck, B. P. & Kroon, J. 2000 Structure predictions allowing more than one molecule in the asymmetric unit. Acta Crystallogr. B56, 535-542. (doi:10.1107/S0108768100000276)
    • (2000) Acta Crystallogr. , vol.B56 , pp. 535-542
    • Van Eijck, B.P.1    Kroon, J.2
  • 27
    • 0033531678 scopus 로고    scopus 로고
    • Pseudopolymorphism: Occurrences of hydrogen bonding organic solvents in molecular crystals
    • Nangia, A. & Desiraju, G. R. 1999 Pseudopolymorphism: occurrences of hydrogen bonding organic solvents in molecular crystals. Chem. Commun. 605-606. (doi:10.1039/A809755K) (Pubitemid 29158703)
    • (1999) Chemical Communications , Issue.7 , pp. 605-606
    • Nangia, A.1    Desiraju, G.R.2
  • 28
    • 33751291245 scopus 로고    scopus 로고
    • Crystallographic studies of supramolecular synthons in amine solvates of trans-1,5-dichloro-9,10-diethynyl-9,10-dihydroanthracene-9,10-diol
    • DOI 10.1021/cg060258m
    • Mondal, R., Howard, J. A. K., Banerjee, R. & Desiraju, G. R. 2006 Crystallographic studies of supramolecular synthons in amine solvates of trans-1,5-dichloro-9,10- diethynyl-9,10- dihydroanthracene-9,10-diol. Cryst. Growth Des. 6, 2507-2516. (doi:10.1021/cg060258m) (Pubitemid 44799880)
    • (2006) Crystal Growth and Design , vol.6 , Issue.11 , pp. 2507-2516
    • Mondal, R.1    Howard, J.A.K.2    Banerjee, R.3    Desiraju, G.R.4
  • 29
    • 0742325413 scopus 로고    scopus 로고
    • C-H·· interactions in ethynylbenzenes: The crystal structures of ethynylbenzene and 1,3,5-triethynylbenzene, and a redetermination of the structure of 1,4-diethynylbenzene
    • Weiss, H.-C., Blaser, D., Boese, R., Doughan, B. M. & Haley, M. M. 1997 C-H· · · p interactions in ethynylbenzenes: the crystal structures of ethynylbenzene and 1,3,5-triethynylbenzene, and a redetermination of the structure of 1,4-diethynylbenzene. Chem. Commun. 1703-1704. (doi:10.1039/a704070i) (Pubitemid 127495497)
    • (1997) Chemical Communications , Issue.18 , pp. 1703-1704
    • Weiss, H.-C.1    Blaser, D.2    Boese, R.3    Doughan, B.M.4    Haley, M.M.5
  • 30
    • 35548980480 scopus 로고    scopus 로고
    • Nearly isostructural polymorphs of ethynylbenzene: Resolution of ≡CH··(arene) and cooperative (C·C) interactions by pressure freezing
    • DOI 10.1021/ja074885r
    • Dziubek, K., Podsiadio, M. & Katrusiak, A. 2007 Nearly isostructural polymorphs of ethynylbenzene: resolution of ≡CH· · · p (arene) and cooperative ≡CH· · · p(C≡C) interactions by pressure freezing. J. Am. Chem. Soc. 129, 12 620-12 621. (doi:10.1021/ja074885r) (Pubitemid 350004445)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.42 , pp. 12620-12621
    • Dziubek, K.1    Podsiadlo, M.2    Katrusiak, A.3
  • 31
    • 0141487885 scopus 로고    scopus 로고
    • Should solid-state molecular packing have to obey the rules of crystallographic symmetry?
    • DOI 10.1039/b304631a, 32
    • Steed, J. W. 2003 Should solid-state molecular packing have to obey the rules of crystallographic symmetry? CystEngComm 5, 169-179. (doi:10.1039/ B304631A) (Pubitemid 40447044)
    • (2003) CrystEngComm , vol.5 , pp. 169-179
    • Steed, J.W.1
  • 32
    • 35648986121 scopus 로고    scopus 로고
    • High Z polymorphs have shorter C-H· · ·o interactions and O-H· · ·o hydrogen bonds
    • (doi:10.1039/B711739F)
    • Babu, N. J. & Nangia, A. 2007 High Z polymorphs have shorter C-H· · ·O interactions and O-H· · ·O hydrogen bonds. CystEngComm 9, 980-983. (doi:10.1039/B711739F)
    • (2007) CystEngComm , vol.9 , pp. 980-983
    • Babu, N.J.1    Nangia, A.2
  • 33
    • 33644835088 scopus 로고    scopus 로고
    • Synthon evolution and unit cell evolution during crystallisation. A study of symmetryindependent molecules (Z >1) in crystals of some hydroxy compounds
    • (doi:10.1039/b514076e)
    • Das, D., Banerjee, R., Mondal, R., Howard, J. A. K., Boese, R. & Desiraju, G. R. 2006 Synthon evolution and unit cell evolution during crystallisation. A study of symmetryindependent molecules (Z >1) in crystals of some hydroxy compounds. Chem. Commun. 555-557. (doi:10.1039/b514076e)
    • (2006) Chem. Commun. , pp. 555-557
    • Das, D.1    Banerjee, R.2    Mondal, R.3    Howard, J.A.K.4    Boese, R.5    Desiraju, G.R.6
  • 34
    • 0037878049 scopus 로고    scopus 로고
    • Searching for a polymorph: Second crystal form of 6-amino-2- phenylsulfonylimino-1,2-dihydropyridine
    • DOI 10.1002/anie.200250660
    • Jetti, R. K. R., Boese, R., Sarma, J. A. R. P., Reddy, L. S., Vishweshwar, P. & Desiraju, G. R. 2003 Searching for a polymorph: second crystal form of 6-amino-2-phenylsulfonylimino-1,2- dihydropyridine. Angew. Chem. Int. Ed. 42, 1963-1967. (doi:10.1002/anie.200250660) (Pubitemid 36565811)
    • (2003) Angewandte Chemie - International Edition , vol.42 , Issue.17 , pp. 1963-1967
    • Jetti, R.K.R.1    Boese, R.2    Sarma, J.A.R.P.3    Reddy, L.S.4    Vishweshwar, P.5    Desiraju, G.R.6
  • 35
    • 70350284586 scopus 로고    scopus 로고
    • Unmasking a third polymorph of a benchmark crystal-structureprediction compound
    • (doi:10.1002/anie.200903285)
    • Roy, S. & Matzger, A. J. 2009 Unmasking a third polymorph of a benchmark crystal-structureprediction compound. Angew. Chem. Int. Ed. 48, 8505-8508. (doi:10.1002/anie.200903285)
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 8505-8508
    • Roy, S.1    Matzger, A.J.2
  • 36
    • 4143077141 scopus 로고    scopus 로고
    • Structural variations and polymorphism of some derivatives of 6-amino-2-phenylsulfonylimino-1,2-dihydropyridine
    • DOI 10.1021/cg049912t
    • Kirchner, M. T., Reddy, L. S., Desiraju, G. R., Jetti, R. K. R. & Boese, R. 2004 Structural variations and polymorphism of some derivatives of 6-amino-2-phenylsulfonylimino- 1,2-dihydropyridine. Cryst. Growth Des. 4, 701-709. (doi:10.1021/cg049912t) (Pubitemid 39091294)
    • (2004) Crystal Growth and Design , vol.4 , Issue.4 , pp. 701-709
    • Kirchner, M.T.1    Reddy, L.S.2    Desiraju, G.R.3    Jetti, R.K.R.4    Boese, R.5
  • 37
    • 37549039510 scopus 로고    scopus 로고
    • A short history of SHELX
    • (doi:10.1107/S0108767307043930)
    • Sheldrick, G. M. 2008 A short history of SHELX. Acta Crystallogr. A64, 112-122. (doi:10.1107/S0108767307043930)
    • (2008) Acta Crystallogr. , vol.A64 , pp. 112-122
    • Sheldrick, G.M.1
  • 38
    • 0141452964 scopus 로고    scopus 로고
    • WinGX suite for small-molecule single-crystal crystallography
    • Farrugia, L. J. 1999 WinGX suite for small-molecule single-crystal crystallography. J. Appl. Crystallogr. 32, 837-838. (doi:10.1107/ S0021889899006020) (Pubitemid 129794704)
    • (1999) Journal of Applied Crystallography , vol.32 , Issue.4 , pp. 837-838
    • Farrugia, L.J.1


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