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

Kudryavtsev, K.V.; Ivantcova, P.M.; Churakov, A.V.

doi:10.1107/S1600536812051471

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 (C-C) = 0.002 Å
R = 0.041
wR = 0.115
Data-to-parameter ratio = 16.0
Details

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

Konstantin V. Kudryavtsev,^a,^b ^* Polina M. Ivantcova ^a and Andrei V. Churakov ^c

^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-HO 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 (2008); Kudryavtsev & Zagulyaeva (2008); Kudryavtsev et al. (2011).

Experimental

Crystal data

C₁₆H₁₅F₃N₂O₄
M_r = 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 radiation
= 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) T_min = 0.955, T_max = 0.968
28987 measured reflections
4585 independent reflections
3698 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.115
S = 1.05
4585 reflections
286 parameters
All H-atom parameters refined
_max = 0.41 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O3ⁱ	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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.
Kudryavtsev, K. V., Churakov, A. V. & Dogan, O. (2011). Acta Cryst. E67, o3186.
Kudryavtsev, K. V. & Irkha, V. V. (2005). Molecules, 10, 755-761.
Kudryavtsev, K. V. & Zagulyaeva, A. A. (2008). Russ. J. Org. Chem. 44, 378-387.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds