[Journal logo]

Volume 69 
Part 1 
Pages o144-o145  
January 2013  

Received 3 December 2012
Accepted 18 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.043
wR = 0.090
Data-to-parameter ratio = 7.2
Details
Open access

(R,R)-1-Acetyl-1'-(2,4,6-trinitrophenyl)-2,2'-bipyrrolidine

aDepartment of Organic Chemistry, Gdansk University of Technology, 80-233 Gdansk, Poland, and bFaculty of Chemistry, Adam Mickiewicz University, 60-780 Poznan, Poland
Correspondence e-mail: kateichs@student.pg.gda.pl

The structure of the title molecule, C16H19N5O7, is mainly determined by the steric effect of a bulky 2,4,6-trinitrophenyl group attached to the N atom of a pyrrolidine ring. Both pyrrolidine rings adopt an envelope conformation, with one of the methylene C atoms as the flap in each case, and the N-C-C-N torsion angle along the bond connecting the two pyrrolidine rings is -174.9 (2)°. The benzene ring of the 2,3,5-trinitrophenyl substituent is deformed and the r.m.s. deviation of its six atoms from the best plane is 0.026 Å. The N atoms of the two nitro groups in the ortho positions deviate from the best plane of the benzene ring by -0.033 (5) and 0.385 (5) Å. These groups, as well as the pyrrolidine ring, are twisted relative to the aromatic ring in the same direction, their best planes forming dihedral angles of 30.2 (2), 64.8 (1) and 46.6 (2)°, respectively, with the ring. An intramolecular C-H...O hydrogen bond occurs. In the crystal, there is a short [O...C = 3.019 (4) Å] contact between a nitro O atom and a C atom of the benzene ring bearing the nitro group and a C-H...O interaction between a methyl H atom and another nitro O atom.

Related literature

For crystal structures of related 1-amino-2,4,6-trinitrobenzenes, see: Butcher et al. (1992[Butcher, R. J., Gilardi, R., Flippen-Anderson, J. L. & George, C. (1992). New J. Chem. 16, 679-692.]); Baggio et al. (1997[Baggio, R., Remedi, M. V., Garland, M. T. & Bujan, E. I. (1997). J. Chem. Crystallogr. 27, 499-505.]).

[Scheme 1]

Experimental

Crystal data
  • C16H19N5O7

  • Mr = 393.36

  • Orthorhombic, P 21 21 21

  • a = 8.1989 (5) Å

  • b = 10.4442 (6) Å

  • c = 20.8877 (13) Å

  • V = 1788.63 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 293 K

  • 0.20 × 0.20 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.990, Tmax = 1.000

  • 7678 measured reflections

  • 1818 independent reflections

  • 1477 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.090

  • S = 1.06

  • 1818 reflections

  • 254 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O1 0.98 2.18 2.891 (4) 129
C18-H18C...O2i 0.96 2.51 3.454 (5) 168
Symmetry code: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5033 ).


References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Baggio, R., Remedi, M. V., Garland, M. T. & Bujan, E. I. (1997). J. Chem. Crystallogr. 27, 499-505.  [CrossRef] [ChemPort]
Butcher, R. J., Gilardi, R., Flippen-Anderson, J. L. & George, C. (1992). New J. Chem. 16, 679-692.  [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o144-o145   [ doi:10.1107/S1600536812051161 ]

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.