Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 8 (August 2013)


organic compounds



Acta Cryst. (2013). C69, 915-919    [ doi:10.1107/S0108270113017563 ]

Two methyl 3-(1H-pyrazol-4-yl)octa­hydro­pyrrolo­[3,4-c]pyrrole-1-carboxyl­ates form different hydrogen-bonded sheets

J. Quiroga, J. Gálvez, J. Cobo and C. Glidewell

Abstract: In the mol­ecules of both methyl (1RS,3SR,3aRS,6aSR)-1-methyl-3-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-4,6-dioxo-5-phenyl­octa­hydro­pyrrolo­[3,4-c]pyrrole-1-carboxyl­ate, C25H24N4O4, (I), and methyl (1RS,3SR,3aRS,6aSR)-5-(4-chlorophen­yl)-1-methyl-3-(3-methyl-1-phenyl-1H-pyrazol-4-yl)-4,6-dioxo­octa­hydro­pyrrolo­[3,4-c]pyrrole-1-carboxyl­ate, C25H23ClN4O4, (II), the two rings of the pyrrolo­pyrrole fragment are both nonplanar, with conformations close to half-chair forms. The overall conformations of the mol­ecules of (I) and (II) are very similar, apart from the orientation of the ester function. The mol­ecules of (I) are linked into sheets by a combination of an N-H...[pi](pyrrole) hydrogen bond and three independent C-H...O hydrogen bonds. The mol­ecules of (II) are also linked into sheets, which are generated by a combination of an N-H...N hydrogen bond and two inde­pendent C-H...O hydrogen bonds, weakly augmented by a C-H...[pi](arene) hydrogen bond.

Formula: C25H24N4O4 and C25H23ClN4O4

Keywords: crystal structure; hydrogen bonding; supramolecular assemblies; pyrazole derivatives; pyrrolopyrrole derivatives.


hkldisplay filedownload file

Structure factor file (CIF format) (250.3 kbytes)
[ doi:10.1107/S0108270113017563/sf3204Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (254.7 kbytes)
[ doi:10.1107/S0108270113017563/sf3204IIsup3.hkl ]
Contains datablock II


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