[Journal logo]

Volume 69 
Part 2 
Pages o161-o162  
February 2013  

Received 16 December 2012
Accepted 20 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.115
Data-to-parameter ratio = 16.0
Details
Open access

(1SR,3RS,3aSR,6aRS)-Methyl 5-methyl-4,6-dioxo-3-[2-(trifluoromethyl)phenyl]octahydropyrrolo[3,4-c]pyrrole-1-carboxylate

aDepartment of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russian Federation,bInstitute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka 142432, Moscow Region, Russian Federation, and cInstitute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii prosp. 31, Moscow 119991, Russian Federation
Correspondence e-mail: kudr@org.chem.msu.ru

In the title compound, C16H15F3N2O4, the relative stereochemistry of the four stereogenic C atoms has been determined. The carboxymethyl and 2-(trifluoromethyl)phenyl substituents of the pyrrolidine cycle have a cis mutual arrangement. The five-membered saturated azacycle adopts an envelope conformation with the N atom occupying the flap position. In the crystal, adjacent molecules are combined in centrosymmetric dimers by two weak N-H...O hydrogen bonds.

Related literature

For general background to the chemistry affording bicyclic pyrrolo[3,4-c]pyrrole-based scaffolds and structural determination, see: Kudryavtsev & Irkha (2005[Kudryavtsev, K. V. & Irkha, V. V. (2005). Molecules, 10, 755-761.]); Kudryavtsev (2008[Kudryavtsev, K. V. (2008). Russ. Chem. Bull. 57, 2364-2372.]); Kudryavtsev & Zagulyaeva (2008[Kudryavtsev, K. V. & Zagulyaeva, A. A. (2008). Russ. J. Org. Chem. 44, 378-387.]); Kudryavtsev et al. (2011[Kudryavtsev, K. V., Churakov, A. V. & Dogan, O. (2011). Acta Cryst. E67, o3186.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15F3N2O4

  • Mr = 356.30

  • Orthorhombic, P b c a

  • a = 11.6168 (4) Å

  • b = 12.7385 (5) Å

  • c = 21.2429 (8) Å

  • V = 3143.5 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 150 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.955, Tmax = 0.968

  • 28987 measured reflections

  • 4585 independent reflections

  • 3698 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.115

  • S = 1.05

  • 4585 reflections

  • 286 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3i 0.884 (15) 2.363 (15) 3.1738 (13) 152.5 (13)
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2094 ).


Acknowledgements

This study was partially supported by the Russian Foundation for Basic Research (project Nos 11-03-00630_a, 11-03-91375-ST_a and 12-03-92005-NNS_a).

References

Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kudryavtsev, K. V. (2008). Russ. Chem. Bull. 57, 2364-2372.  [ISI] [CrossRef] [ChemPort]
Kudryavtsev, K. V., Churakov, A. V. & Dogan, O. (2011). Acta Cryst. E67, o3186.  [CSD] [CrossRef] [details]
Kudryavtsev, K. V. & Irkha, V. V. (2005). Molecules, 10, 755-761.  [CrossRef] [PubMed] [ChemPort]
Kudryavtsev, K. V. & Zagulyaeva, A. A. (2008). Russ. J. Org. Chem. 44, 378-387.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o161-o162   [ doi:10.1107/S1600536812051471 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.