Acta Crystallographica Section B

Structural Science

Volume 68, Part 6 (December 2012)

research papers

Acta Cryst. (2012). B68, 667-676    [ doi:10.1107/S0108768112039651 ]

Solvatomorphism of 9,9'-[1,3,4-thiadiazole-2,5-diylbis(2,3-thiophendiyl-4,1-phenylene)]bis[9H-carbazole]: isostructurality, modularity and order-disorder theory

B. Stöger, P. Kautny, D. Lumpi, E. Zobetz and J. Fröhlich

Abstract: During a systematic investigation of the crystallization behaviour of 9,9'-[1,3,4-thiadiazole-2,5-diylbis(2,3-thiophendiyl-4,1-phenylene)]bis[9H-carbazole] (I), six single crystalline solvates were obtained and characterized by X-ray diffraction at 100 K. The structure of the hemi-2-butanone (MEK) solvate contains two crystallographically independent molecules of (I) related by pseudo-inversion symmetry. The structure is polytypic and composed of non-polar (I) layers and polar solvent layers. It can be described according to an extended order-disorder (OD) theory with relaxed vicinity condition. The observed polytype is of a maximum degree of order (MDO). Layer triples of the second MDO polytype are shown by twinning by inversion. The mono-benzene and mono-toluene solvates are isostructural. Whereas the (I) layers are isostructural to those of the idealized description of the hemi-MEK solvate, the solvent layers are non-polar, resulting in a fully ordered structure. The toluene molecule is ordered, the benzene molecule features disorder. The (I) layers in the sesqui-dioxane and sesqui-benzene solvates are isostructural and unrelated to those in the hemi-MEK, mono-benzene and mono-toluene solvates. The solvent layers are isopointal in both sesqui-solvates, but the stacking differs significantly. The hemi-dideuterodichloromethane (DCM-d2) solvate is made up of two kinds of (I) rods, spaced by DCM-d2 molecules. Rods of one kind are similar to analogous rods in the sesqui-dioxane and the sesqui-benzene solvates, whereas rods of the other kind are only remotely related to rods in the hemi-MEK solvate.

Keywords: solvatomorphism; pseudo-inversion symmetry; order-disorder theory; twinning.

hkldisplay filedownload file

Structure factor file (CIF format) (756.8 kbytes)
[ doi:10.1107/S0108768112039651/ry5046hemi_meksup2.hkl ]
Contains datablock hemi_mek

hkldisplay filedownload file

Structure factor file (CIF format) (601.2 kbytes)
[ doi:10.1107/S0108768112039651/ry5046mono_benzenesup3.hkl ]
Contains datablock mono_benzene

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Structure factor file (CIF format) (497.8 kbytes)
[ doi:10.1107/S0108768112039651/ry5046mono_toluenesup4.hkl ]
Contains datablock mono_toluene

hkldisplay filedownload file

Structure factor file (CIF format) (939.0 kbytes)
[ doi:10.1107/S0108768112039651/ry5046sesqui_dioxanesup5.hkl ]
Contains datablock sesqui_dioxane

hkldisplay filedownload file

Structure factor file (CIF format) (426.3 kbytes)
[ doi:10.1107/S0108768112039651/ry5046sesqui_benzenesup6.hkl ]
Contains datablock sesqui_benzene

hkldisplay filedownload file

Structure factor file (CIF format) (738.8 kbytes)
[ doi:10.1107/S0108768112039651/ry5046hemi_dcmsup7.hkl ]
Contains datablock hemi_dcm


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