(2R)-8-Benzyl-2-[(S)-hy­droxy(phen­yl)meth­yl]-8-aza­bicyclo­[3.2.1]octan-3-one

Brzezinski, K.; Lazny, R.; Sienkiewicz, M.; Wojtulewski, S.; Dauter, Z.

doi:10.1107/S1600536811053190

Volume 68
Part 1
Pages o149-o150
January 2012

Received 4 November 2011
Accepted 9 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.027
wR = 0.070
Data-to-parameter ratio = 15.2
Details

(2R)-8-Benzyl-2-[(S)-hydroxy(phenyl)methyl]-8-azabicyclo[3.2.1]octan-3-one

Krzysztof Brzezinski,^a ^* Ryszard Lazny,^b Michal Sienkiewicz,^b Slawomir Wojtulewski ^b and Zbigniew Dauter ^a

^aSynchrotron Radiation Research Section, MCL, National Cancer Institute, Argonne National Laboratory, Biosciences Division, Bldg. 202, Argonne, IL 60439, USA, and ^bInstitute of Chemistry, University of Bialystok, Hurtowa 1, 15-399 Bialystok, Poland
Correspondence e-mail: kbrzezinski@anl.gov

The crystal of the title compound, C₂₁H₂₃NO₂, was chosen from a conglomerate formed by a racemic mixture. An intramolecular hydrogen bond is formed between hydroxy group and heterocyclic N atom of the azabicyclo[3.2.1]octan-3-one system. The crystal structure is stabilized by C-HO interactions between aliphatic C-H groups and the carbonyl O atom. For the title chiral crystal, the highly redundant and accurate diffraction data set collected with low energy copper radiation gave a Flack parameter of 0.12 (18) for anomalous scattering effects originating from O atoms.

Related literature

For recent background literature on the chemistry of related tropane-derived aldols and their applications, including stereoselective syntheses of bioactive alkaloids, see: Lazny et al. (2011); Sienkiewicz et al. (2009) and references cited therein. For stereoselective syntheses of related nortropinone aldols, see: Lazny et al. (2001); Lazny & Nodzewska (2003). For a representative review of the biological activity of tropane derivatives, see: Singh (2000).

Experimental

Crystal data

C₂₁H₂₃NO₂
M_r = 321.40
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.9354 (1) Å
b = 13.3091 (2) Å
c = 22.1511 (3) Å
V = 1749.82 (5) Å³
Z = 4
Cu K radiation
= 0.61 mm^-1
T = 100 K
0.65 × 0.25 × 0.19 mm

Data collection

Oxford Diffraction SuperNova Dual diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011) T_min = 0.75, T_max = 0.89
32829 measured reflections
3323 independent reflections
3276 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.070
S = 1.18
3323 reflections
218 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 1257 Friedel pairs
Flack parameter: 0.12 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O9-H9N8	0.84	1.99	2.7280 (13)	146
C6-H6BO3ⁱ	0.99	2.61	3.3414 (15)	131
C7-H7AO3ⁱ	0.99	2.52	3.2954 (15)	135
C16-H16AO3ⁱ	0.99	2.60	3.5846 (16)	173
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXD (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and pyMOL (DeLano, 2002); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2429 ).

Acknowledgements

This work was supported in part by the University of Bialystok (BST-125), the Polish Ministry of Science and Higher Education (grant No. N N204 546939), the Intramural Research Program of the NIH, National Cancer Institute, Center for Cancer Research, and with Federal funds from the National Cancer Institute, National Institutes of Health, under contract HHSN2612008000001E.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
DeLano, W. L. (2002). The pyMOL Molecular Graphics System. DeLano Scientific, San Carlos, CA, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Lazny, R. & Nodzewska, A. (2003). Tetrahedron Lett. 44, 2441-2444.
Lazny, R., Nodzewska, A. & Tomczuk, I. (2011). Tetrahedron Lett. 52, 5680-5683.
Lazny, R., Sienkiewicz, M. & Bräse, S. (2001). Tetrahedron, 57, 5825-5832.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sienkiewicz, M., Wilkaniec, U. & Lazny, R. (2009). Tetrahedron Lett. 50, 7196-7198.
Singh, S. (2000). Chem. Rev. 100, 925-1024.

organic compounds