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  • 11
    Electronic Resource
    Electronic Resource
    Comparison of the structures of 1,5-dichloro- and 1,5-dibromonaphthalene-2,6-diol and their co-crystalline compounds with dioxane (1995)
    Springer
    Journal of inclusion phenomena and macrocyclic chemistry 23 (1995), S. 313-327 
    Details
    ISSN: 1573-1111
    Keywords: Phenols ; dioxane ; hydrogen bonding ; screw axes ; aromatic ring interactions ; weak attractive forces
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The 1,5-dichloro-(1) and 1,5-dibromo-(2) naphthalene-2,6-diols form isostructural lattices incorporating ...O−H...O−H...O−H... hydrogen bonding surrounding 21 screw axes. Each phenolic hydroxy group participates in one donor and one acceptor hydrogen bond. When crystallised from dioxane, both compounds form new 1:1 co-crystalline materials whose lattices are closely related but not isostructural. All inter-phenolic hydrogen bonding is now absent with each hydroxy group acting instead as a donor to a dioxane oxygen atom. In consequence, the hydrogen bonded layer structures of pure1 or2 are now replaced by hydrogen bonded chain arrangements. All four crystal structures are analysed and compared in crystal engineering terms through discussion of the various types of other weak intermolecular attractions involved in their lattice constructions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00707935
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  • 12
    Electronic Resource
    Electronic Resource
    Ritter reactions. VIII. Inclusion compounds formed betweenN-(5H-Dibenzo[a, d]cycloheptyl)acetamides and dioxane (1994)
    Springer
    Journal of inclusion phenomena and macrocyclic chemistry 18 (1994), S. 149-160 
    Details
    ISSN: 1573-1111
    Keywords: Amide hosts ; dioxane ; hydrogen bonding ; Ritter reaction ; −C−H⋯O-hydrogen bonds
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract 5H-Dibenzo[a, d]cyclohepten-5-ol2 and its saturated analogue4 undergo Ritter reactions with acetonitrile and sulfuric acid to afford the acetamide derivatives3 or5 respectively. Both products form unstable inclusion compounds when crystallised from dioxane. The crystal structure of the dioxane compound of3 is reported. This material [(C17H15NO)·(C4H8O2)2,Pnma,a=9.616(1),b=23.280(2),c=10.298(1) Å,Z=4,R=0.054] has the amide molecules arranged in parallel chains by means of intermolecular −N−H⋯O=C hydrogen bonds. The inclusion compound is stabilised by means of −C−H⋯O-hydrogen bonds. Each dioxane molecule is involved in five such interactions to neighbouring molecules of3 and dioxane.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00705818
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  • 13
    Electronic Resource
    Electronic Resource
    The design and synthesis of a family of multimolecular host-guest inclusion complexes (1984)
    Springer
    Journal of inclusion phenomena and macrocyclic chemistry 2 (1984), S. 75-83 
    Details
    ISSN: 1573-1111
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The discovery thatexo-2,exo-6-dihydroxy-2,6-dimethylbicyclo [3.3.1]nonane (2) forms novel multimolecular canal-type inclusion complexes has led to a systematic study of related molecular structures. This synthetic programme has shown that diol (2) is the prototype of a family of host diols all with the same crystallographic space groupP3121, but with distinctly different canal shapes and dimensions. The structures of the first four members of this new family of hosts are described and contrasted.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00663241
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  • 14
    Electronic Resource
    Electronic Resource
    Structure of the co-crystalline solid formed between 1,4-dichloronaphthalene-2,3-diol and dioxane (1994)
    Springer
    Journal of inclusion phenomena and macrocyclic chemistry 20 (1994), S. 267-276 
    Details
    ISSN: 1573-1111
    Keywords: Phenols ; dioxane ; hydrogen bonding ; co-crystals ; aromatic ring interactions ; coronene packing
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The 1,4-dichloro-(1) and 1,4-dibromo-(2) derivatives of naphthalene-2,3-diol crystallise in structures containing acetic acid or dioxane solvent molecules. X-ray crystallographic examination of the compound formed between1 and dioxane is reported here [(C10H6Cl2O2)2·(C4H8O2),P21/c,a=12.358(3),b=4.9930(7),c=19.167(4) Å,β=96.09(1)0,Z=2,R=0.035] and this structure is analysed in crystal engineering terms. The compound is a co-crystalline material involving two types of hydrogen bonding: one phenolic group participates in a $$\begin{gathered} ...{\text{OH }}...{\text{OH }}...{\text{OH}} \hfill \\ {\text{ | | |}} \hfill \\ {\text{ Ar Ar Ar}} \hfill \\ \end{gathered} $$ chain, while the second phenolic group hydrogen bonds to a dioxane. Extension of the hydrogen bonding network through the second dioxane oxygen results in heavily corrugated layers. Neighbouring layers interact by a combination of aromatic face-face and edge-face interactions similar to a partial coronene-type γ packing to complete the structure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00708772
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  • 15
    Electronic Resource
    Electronic Resource
    Helical tubulate inclusion compounds of ferrocene and squalene (1993)
    Springer
    Journal of inclusion phenomena and macrocyclic chemistry 15 (1993), S. 385-398 
    Details
    ISSN: 1573-1111
    Keywords: Hydrogen bonding ; alicyclic diol ; helical tubulate ; crystal structure ; ferrocene ; squalene
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The inclusion compounds of 2,8-dimethyltricyclo[5.3.1.13,9]dodecane-syn-2,syn-8-diol,3, with ferrocene and with squalene have been prepared. The crystal structures of these helical tubulate compounds: (3)3·(ferrocene)0.75 [P3121,a=b=13.7480(6),c=7.0312(5) Å,Z=1,R=0.038] and (3)3·(squalene)0.23 [P3121,a=b=13.677(1),c=7.0533(9) Å,Z=1,R=0.042] are described.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00708755
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  • 16
    Electronic Resource
    Electronic Resource
    Enantiomeric Self-Resolution through Dimethylsulfoxide Complexation (1998)
    Springer
    Journal of inclusion phenomena and macrocyclic chemistry 31 (1998), S. 145-160 
    Details
    ISSN: 1573-1111
    Keywords: hydrogen bonding ; conglomerates ; self-resolution ; co-crystals ; fluorine interactions ; helical tubulands
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The alicyclic diol 2 is known to adopt five different types of crystallattice: the pure solid, cocrystalline compounds with water or certainphenols, and two different types of lattice inclusion system (helicaltubulates and ellipsoidal clathrates). Self-resolution only occurs onforming the helical tubulate inclusion compounds. Its close analogue2,7-bis(trifluoromethyl)tricyclo[4.3.1.13,8]un-decane-syn-2,syn-7-diol 4 was synthesised to examine the influence ofreplacing CH3- by CF3-groups. It no longer formslattice inclusion compounds but does form a cocrystalline solid withdimethyl sulfoxide (DMSO). Crystal structures of 4[C13H16O2F6,P21/c, a 7.8636(6), b 13.1020(7), c 25.319(2) Å, β101.526(4)°, Z 8, R 0.044] and (4)V_2.VD/MSO[(C13H16O2F6)2⋅C2H6SO,P212121, a 7.249(1), b 16.064(3),c 25.347(4) Å, Z 4, R 0.033] were determined. In solid diol 4 themolecules are linked through (–-O–-H)4 rings toproduce layers of chirally pure enantiomers but the net crystal structure,which comprises layers of alternating handedness, is achiral. In contrast,complexation of 4 with DMSO by means of two -–O-–H.O=Shydrogen bonds induces complete enantiomeric self-resolution.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1007958031910
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  • 17
    Electronic Resource
    Electronic Resource
    Molecular determinants of a new family of helical tubuland host diols (1987)
    Springer
    Journal of inclusion phenomena and macrocyclic chemistry 5 (1987), S. 229-232 
    Details
    ISSN: 1573-1111
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The alicyclic diols (1–5) constitute the first members of a family of novel helical tubuland hosts crystallising in space group P3121 but possessing quite different canal shapes and dimensions. Consideration of their structural data has revealed two distinct sub-classes of these materials. The molecular features necessary for a diol to crystallise with the helical tubuland structure are defined and discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00655654
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  • 18
    Electronic Resource
    Electronic Resource
    Guest control of diol inclusion host lattices (1992)
    Springer
    Structural chemistry 3 (1992), S. 59-61 
    Details
    ISSN: 1572-9001
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract A survey of the multimolecular inclusion compounds formed bysyn-2,syn-7-dihydroxy-2,7-dimethyltricyclo[4.3.1.13,8]undecane1 and 34 guest molecules shows that two inclusion crystal structures are commonly obtained, namely the helical tubulate inclusion lattice and the ellipsoidal clathrate structure type. Interactions between host and guest are necessarily weak since the host surface is hydrocarbon. Small differences in the guest molecules can tip the balance between alternative inclusion lattices, one of which is chiral. For the first time precise guest locations in the helical tubulate structure have been obtained by X-ray diffraction analysis. Crystal data:1·CCl4: space groupP3 121,a=13.2812(2),c=6.904(1) Å, unit cell contents 3(C13H22O2) + 1.2CCl4,R=0.044;1·BrCH2CH2CH2Br: space groupP3 121,a=13.206(2),c=6.915(2) Å, unit cell contents 3(C13H22O2)+ BrCH2CH2CH2Br,R=0.042;1.0- xylene: space groupP3 121,a=13.380(2),c=6.905(1) Å, unit cell contents 3(C13H22O2) + 1.2 C8H10,R=0.042.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00671980
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  • 19
    Electronic Resource
    Electronic Resource
    Complexation of Ethanol by a Helical Tubuland Diol Host (1999)
    Springer
    Structural chemistry 10 (1999), S. 169-176 
    Details
    ISSN: 1572-9001
    Keywords: Crystal engineering ; hydrogen bonding ; inclusion ; (O — H)6 cycle ; ethanol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The cage compound 4,7-dimethylpentacyclo[6.3.0.02,6.03,10.05,9]undecane-anti-4,anti-7-diol 3 and its 4,7-bis(d 3-methyl) derivative 4 form 1:1 cocrystalline complexes with ethanol instead of the expected helical tubulate inclusion compounds. The X-ray crystal structure of (4)·(ethanol) [(C13H12D6O2)·(C2H6O), Cmca, a 19.049(2), b 14.932(2), c 10.117(1) Å, Z 8, R 0.061] shows that the key supramolecular synthon is a hydrogen-bonded (O — H)6 cycle of hydroxy groups constructed from two ethanols (in ring positions 1 and 4) and four diols. This uncommon centrosymmetric motif permits efficient lattice packing of ethanol and both diol enantiomers into layers without requiring the self-resolution that would be mandatory in forming the helical tubulate structure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1021880328629
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  • 20
    Electronic Resource
    Electronic Resource
    Preparation and crystal structure ofexo-2,exo-6-dihydroxy-2,6-dimethyl-9-oxabicyclo[3.3.1]nonane (1993)
    Springer
    Structural chemistry 4 (1993), S. 41-51 
    Details
    ISSN: 1572-9001
    Keywords: Crystal structure ; helical tubuland inclusion ; pseudo ¯4 site
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract In a further exploration of the structural factors causing alicyclic diols such asexo-2,exo-6-dihydroxy-2,6-dimethylbicyclo[3.3.1]nonane (1) to adopt the helical tubuland inclusion host structure, the title compound (8) has been synthesized and its crystal structure determined. This 9-oxa analogue of (1) has a totally different structure [C10H18O3; orthorhombic;P21212;a 18.989(4),b 19.064(3),c 14.256(3) Å;Z 20; with finalR 0.065] due to involvement of the ether oxygen atom in the hydrogen bonding network. The structure of the diol (8) approximatesP¯421 c symmetry, and 16 of the 20 molecules per cell create a hostlike structure of this symmetry, which consists of tightly bound hydrogen bonded pillars parallel toc. The remaining guestlike molecules occupy inequivalent pseudo ¯4 sites separated byc/2 to form weakly bound columns parallel toc. Hydrogen bonds also occur between the pillars and columns. An ordered structure with sensible intermolecular contacts can be formed inP212121 with thec axis doubled. A difference betweena andb axial lengths correlates with a difference in occupancies of pseudo-¯4-related sites for the guest-like component of the structure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00672098
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