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

Eichstaedt, K.; Olszewska, T.; Gdaniec, M.

doi:10.1107/S1600536812051161

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 (C-C) = 0.005 Å
R = 0.043
wR = 0.090
Data-to-parameter ratio = 7.2
Details

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

Katarzyna Eichstaedt,^a ^* Teresa Olszewska ^a and Maria Gdaniec ^b

^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-HO hydrogen bond occurs. In the crystal, there is a short [OC = 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-HO 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); Baggio et al. (1997).

Experimental

Crystal data

C₁₆H₁₉N₅O₇
M_r = 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 radiation
= 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) T_min = 0.990, T_max = 1.000
7678 measured reflections
1818 independent reflections
1477 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.090
S = 1.06
1818 reflections
254 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O1	0.98	2.18	2.891 (4)	129
C18-H18CO2ⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); 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.
Butcher, R. J., Gilardi, R., Flippen-Anderson, J. L. & George, C. (1992). New J. Chem. 16, 679-692.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds