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Volumn 41, Issue 20, 2002, Pages 3848-3851

4,4-Diphenyl-2,5-cyclohexadienone: Four polymorphs and nineteen crystallographically independent molecular conformations

Author keywords

Conformation analysis; Hydrogen bonds; Polymorphism; Structure elucidation; Supramolecular chemistry

Indexed keywords

CRYSTAL STRUCTURE; X RAY CRYSTALLOGRAPHY;

EID: 0037131587     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021018)41:20<3848::AID-ANIE3848>3.0.CO;2-L     Document Type: Article
Times cited : (81)

References (35)
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    • G. R. Desiraju, Crystal Engineering. The Design of Organic Solids, Elsevier, Amsterdam, 1989. pp. 285-301. Polymorphism was referred to as the "nemesis of crystal design" over a decade ago. Our understanding of this phenomenon has since improved but it is still difficult to anticipate when and how it will strike (see ref. [4]).
    • (1989) Crystal Engineering. The Design of Organic Solids , pp. 285-301
    • Desiraju, G.R.1
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    • (Ed.: G. R. Desiraju), Elsevier, Armsterdam
    • a) J. Bernstein in Organic Solid State Chemistry (Ed.: G. R. Desiraju), Elsevier, Armsterdam, 1987, pp. 471-518;
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    • J. Bernstein, R. J. Davey, J.-O. Henck, Angew. Chem. 1999, 111, 3646-3669; Angew. Chem. Int. Ed. 1999, 38, 3440-3461. Concomitant polymorphs crystallize simultaneously from the same solvent and in the same crystallizing flask under identical crystal growth conditions.
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    • Bernstein, J.1    Davey, R.J.2    Henck, J.-O.3
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    • J. Bernstein, R. J. Davey, J.-O. Henck, Angew. Chem. 1999, 111, 3646-3669; Angew. Chem. Int. Ed. 1999, 38, 3440-3461. Concomitant polymorphs crystallize simultaneously from the same solvent and in the same crystallizing flask under identical crystal growth conditions.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3440-3461
  • 16
    • 0004210534 scopus 로고
    • Pergamon, Oxford
    • Polymorphism of 1 in terms of type and number of forms is based on the crystallographic analysis of stable structures. Extensive examples of polymorphism may be found in the thermomicroscopy literature (M. Kuhnert-Brand stätter, Thermomicroscopy in the Analysis of Pharmaceuticals, Pergamon, Oxford, 1971) and in Groth's collection (P. H. R. Groth, Chemische Kristallographie, Vol. 1-5, Engelmann, Leipzig, 1906-1919). However, some of these are transient phases observed during heating or cooling without crystallographic confirmation.
    • (1971) Thermomicroscopy in the Analysis of Pharmaceuticals
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  • 17
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    • Engelmann, Leipzig
    • Polymorphism of 1 in terms of type and number of forms is based on the crystallographic analysis of stable structures. Extensive examples of polymorphism may be found in the thermomicroscopy literature (M. Kuhnert-Brand stätter, Thermomicroscopy in the Analysis of Pharmaceuticals, Pergamon, Oxford, 1971) and in Groth's collection (P. H. R. Groth, Chemische Kristallographie, Vol. 1-5, Engelmann, Leipzig, 1906-1919). However, some of these are transient phases observed during heating or cooling without crystallographic confirmation.
    • (1906) Chemische Kristallographie , vol.1-5
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  • 19
    • 2142755525 scopus 로고    scopus 로고
    • note
    • -3, T= 100(2) K, R1 = 0.0589, wR2 = 0.1360 for all data, 6538 independent reflections. CCDC-182230 and -182231 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
  • 20
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    • note
    • There are no examples of conformational crystallization of four polymorphs in reference [6].
  • 25
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    • G. R. Desiraju, Angew Chem. 1995, 107 2541-2558; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327.
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    • G. R. Desiraju, Angew Chem. 1995, 107 2541-2558; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2311-2327
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    • 2, Accelrys, Cambridge, UK, www.accelrys.com.
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    • 2142822516 scopus 로고    scopus 로고
    • note
    • In reference [12], which deals with a database study on polymorphism, there are five clusters with ΔZ′= 3. Data for ΔZ′ > 3 are not reported.
  • 34
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    • note
    • 2 during the course of writing this manuscript. Approximate cell dimensions: a = 8.39, b = 14.56, c = 26.80 Å, α = 90.36°, β = 90.02°, γ = 90.30°. It changes to form B with time.


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