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Molecular Structure Laboratory

Univerisity of Wisconsin-Madison | Department of Chemistry


Updated: December 16, 2011

The Crystallography Laboratory provides single crystal X-ray crystallographic facilites and services to the members of the Department of Chemistry and other collaborators. The laboratory is a part of the Paul Bender Chemical Instrumentation Laboratories that also provide access to major shared resources in NMR, MS, ESR, and IR facilities.

 

News and Quick Links

Upcoming meeting - the 19th Bruker Users Meeting in Madison, WI. September 25-27, 2011.

March 2010. The Cambridge Structural Database is available online to the UW-Madison campus users (for 2010). It is called WebCSD.

 

December 2009. A new Bruker Smart Quazar diffractometer has been installed in the laboratory vastly expanding our capabilities of characterizing small crystals and acquiring charge-density quality data.

 



3. If you need to access your structure - log in to the ReciprocalNet - the in-house database

4. Sample submission form page

5. Notes on OLEX2

Molecule of the year 2011

5-(Pyridin-2-ylmethylene)-3-phenyl-2-methylthio-3,5-dihydro-4H-imidazole-4-one


Top drawing - the title compound (1). The bottom diagram shows three different molecular conformations of 1 in its three polymorphs.

The title compound (1) exists in three polymorphic forms.  Crystalline 1 undergoes an enantiotropic, first order, k2 phase transition at 262.9(5) K with ΔH=0.3(1) kJ/mol.  Upon cooling below the transition temperature, the high temperature orthorhombic polymorph (Form I, space group Pbcm) transforms into a low temperature orthorhombic polymorph (Form II, space group Pbca) with a unit cell twice the size of that of the Form I.  A molten 1 can be cooled in a controlled fashion to generate a monoclinic Form III of 1 with the unit cell size similar to that of Form I.  Metastable Form III, once isolated, is indefinitely stable between 100 K and its melting point of 466 K.  If crystals of Form III are in contact with seed crystals of Form I, a monotropic first-order  Form III→Form I phase transition occurs upon heating with the onset between 420-448 K and ΔH=-1.7(4) kJ/mol.   The most substantial differences among the molecular geometries of 1 in Forms I-III are observed in the position and tilt of the phenyl ring relative to the rest of the molecule.  The packing in Form III is very different from those in the other polymorphs.  DFT molecular geometry optimizations produce the following order of stable molecule configurations: Form II (most stable), Form I (0.50 kJ/mol), Form III (2.81 kJ/mol).

The details of the study are described in the paper "Polymorphism of 5-(pyridin-2-ylmethylene)-3-phenyl-2-methylthio-3,5-
dihydro-4H-imidazole-4-one" by Ilia A. Guzei, Erica M. Gunn, Lara C. Spencer, Jennifer M. Schomaker and Jared W. Rigoli. Reference: CrystEngComm, 2011, 13, 3444-3450.



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