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Volume 69 
Part 8 
Page o1297  
August 2013  

Received 1 July 2013
Accepted 17 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.050
wR = 0.114
Data-to-parameter ratio = 15.2
Details
Open access

N-tert-Butoxycarbonyl-[alpha]-(2-fluorobenzyl)-L-proline

aDepartment of Physics, Thiagarajar College, Madurai 625 009, India, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800-USM, Penang, Malaysia
Correspondence e-mail: vasan692000@yahoo.co.in

In the title compound, C17H22FNO4, the pyrrolidine ring adopts an envelope conformation with the disordered components of the methylene C atom, with site occupancies of 0.896 (7) and 0.104 (7), being the flap on either side of the mean plane involving the other atoms of the ring. The carboxylic acid group forms dihedral angles of 72.06 (11) and 45.44 (5)° with the N-tert-butoxycarbonyl group and the 2-fluorobenzyl group, respectively. In the crystal, two-dimensional layers of molecules parallel to (001) are built through an R44(23) motif generated via O-H...O, C-H...O and C-H...F interactions, and an R22(11) motif generated by C-H...O and C-H...F interactions.

Related literature

For general background, see: Taylor et al. (1998[Taylor, P. P., Pantaleone, D. P., Senkpeil, R. F. & Fotheringham, I. G. (1998). Trends Biotechnol. 16, 412-418.]); Jeng et al. (2002[Jeng, A. Y., Savage, P., Beil, M. E., Bruseo, C. W., Hoyer, D., Fink, C. A. & Trapani, A. J. (2002). Clin. Sci. 103, 98-101.]); Anderson et al. (2004[Anderson, J. C., Wu, N., Santoro, S. W., Lakshman, V., King, D. S. & Schultz, P. G. (2004). Proc. Natl Acad. Sci. USA, 101, 7566-7571.]); Ryder et al. (2000[Ryder, T. R., Hu, L. Y., Rafferty, M. F., Lotarski, S. M., Rock, D. M., Stoehr, S. J. & Szoke, B. G. (2000). Drug Des. Discov. 16, 317-322.]). For biological activity of the title compound, see: Tamazyan et al. (2004[Tamazyan, R., Karapetyan, H., Martirisyan, A., Martirosyan, V., Harutyunyan, G. & Gasparyan, S. (2004). Acta Cryst. C60, o390-o392.]). For graph-set notation of hydrogen bonding, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H22FNO4

  • Mr = 323.36

  • Orthorhombic, P 21 21 21

  • a = 10.4777 (1) Å

  • b = 12.4283 (2) Å

  • c = 13.1550 (2) Å

  • V = 1713.04 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.54 × 0.34 × 0.24 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.962, Tmax = 0.977

  • 14001 measured reflections

  • 3426 independent reflections

  • 2712 reflections with I > 2[sigma](I)

  • Rint = 0.031

  • Standard reflections: 0

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.114

  • S = 1.06

  • 3426 reflections

  • 225 parameters

  • 8 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15A...F1i 0.95 2.59 3.378 (3) 141
C16-H16A...O1i 0.95 2.60 3.541 (3) 173
O1-H1...O3ii 0.89 (3) 1.73 (3) 2.611 (2) 173 (3)
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLUTON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2586 ).


Acknowledgements

The authors thank Dr Mutharasu Devarajan, Associate Professor, and the staff of the X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, for their help in the data collection.

References

Anderson, J. C., Wu, N., Santoro, S. W., Lakshman, V., King, D. S. & Schultz, P. G. (2004). Proc. Natl Acad. Sci. USA, 101, 7566-7571.  [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Jeng, A. Y., Savage, P., Beil, M. E., Bruseo, C. W., Hoyer, D., Fink, C. A. & Trapani, A. J. (2002). Clin. Sci. 103, 98-101.
Ryder, T. R., Hu, L. Y., Rafferty, M. F., Lotarski, S. M., Rock, D. M., Stoehr, S. J. & Szoke, B. G. (2000). Drug Des. Discov. 16, 317-322.  [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Tamazyan, R., Karapetyan, H., Martirisyan, A., Martirosyan, V., Harutyunyan, G. & Gasparyan, S. (2004). Acta Cryst. C60, o390-o392.  [CrossRef] [IUCr Journals]
Taylor, P. P., Pantaleone, D. P., Senkpeil, R. F. & Fotheringham, I. G. (1998). Trends Biotechnol. 16, 412-418.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1297  [ doi:10.1107/S1600536813019788 ]

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