2-Propyl 3,3-dibromo-2-hydroxy­pyrrolidine-1-carboxyl­ate

Nichol, G.S.; Gunawan, S.; Xu, Z.; Dietrich, J.; Hulme, C.

doi:10.1107/S1600536810005106

Volume 66
Part 3
Page o597
March 2010

Received 29 January 2010
Accepted 8 February 2010
Online 13 February 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.082
Data-to-parameter ratio = 69.4
Details

2-Propyl 3,3-dibromo-2-hydroxypyrrolidine-1-carboxylate

Gary S. Nichol,^a ^* Steven Gunawan,^b Zhigang Xu,^b Justin Dietrich ^b and Christopher Hulme ^b

^aDepartment of Chemistry and Biochemistry, The University of Arizona, 1306 E. University Boulevard, Tucson, AZ 85721, USA, and ^bSouthwest Center for Drug Discovery and Development, College of Pharmacy, BIO5 Institute, University of Arizona, Tucson, AZ 85721, USA
Correspondence e-mail: gsnichol@email.arizona.edu

The title compound, C₈H₁₃Br₂NO₃, crystallizes as a non-merohedral twin with twin law -0.6 0 0.4/0 - 1 0 /1.6 0 0.6, and the structure has a refined twin domain ratio of 0.546 (5). The structure shows a compact conformation, with the ester unit roughly coplanar with a mean plane fitted through the non-H atoms of the pyrrolidine ring [dihedral angle = 8.23 (9)°]. In the crystal, inversion dimers linked by pairs of O-HO hydrogen bonds generate an R²₂(12) motif.

Related literature

For details of the synthesis, see: Magnus et al. (1994); Salamant & Hulme (2006). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bonding motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₈H₁₃Br₂NO₃
M_r = 331.01
Monoclinic, P 2₁ /n
a = 10.1061 (5) Å
b = 5.9914 (3) Å
c = 18.5496 (9) Å
= 95.880 (2)°
V = 1117.26 (10) Å³
Z = 4
Mo K radiation
= 7.24 mm^-1
T = 100 K
0.44 × 0.16 × 0.11 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: multi-scan (TWINABS; Sheldrick, 1996) T_min = 0.144, T_max = 0.514
34994 measured reflections
9572 independent reflections
7956 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.082
S = 1.03
9572 reflections
138 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 1.41 e Å^-3
_min = -0.77 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1OO2ⁱ	0.83 (3)	1.92 (3)	2.7479 (16)	176 (3)
Symmetry code: (i) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT and CELL_NOW (Sheldrick, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL and local programs.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2278 ).

Acknowledgements

The diffractometer was purchased with funding from NSF grant No. CHE-0741837.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Magnus, P., Hulme, C. & Weber, W. (1994). J. Am. Chem. Soc. 116, 4501-4502.
Salamant, W. & Hulme, C. (2006). Tetrahedron Lett. 47, 605-609.
Sheldrick, G. M. (1996). TWINABS. University of Göttingen, Germany.
Sheldrick, G. M. (2004). CELL_NOW. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds