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Volume 69 
Part 6 
Page o927  
June 2013  

Received 6 May 2013
Accepted 15 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.086
Data-to-parameter ratio = 15.7
Details
Open access

[(2R,3R)-3-(4-Nitrophenyl)aziridin-2-yl]methanol monohydrate

aUMR 990, INSERM, Université d'Auvergne, Laboratoire de Chimie Physique, Faculté de Pharmacie, 63001 Clermont-Ferrand, France,bLaboratoire de Chimie Thérapeutique, Faculté de Pharmacie, Université d'Auvergne, 63001 Clermont-Ferrand, France, and cSamara State University, 433011 Samara, Russian Federation
Correspondence e-mail: vincent.gaumet@udamail.fr

The title monohydrate, C9H10N2O3·H2O, contains an aziridine ring including two contiguous stereocenters, both of which exhibit an R configuration. The methylhydroxy and nitrophenyl groups are cis-disposed about the aziridine ring. The mean plane of the benzene ring is tilted to the aziridine ring by 66.65 (8)°. The nitro group is nearly coplanar with the benzene ring [dihedral angle = 2.5 (2)°]. In the crystal, the components are linked by N-H...O, O-H...N and O-H...O hydrogen bonds, generating supramolecular layers parallel to (001).

Related literature

For the biological activity of aziridine derivatives, see: Li et al. (1995[Li, V., Choi, D., Tang, M. & Kohn, H. (1995). J. Biochem. 34, 7120-7126.]); Sheldon et al. (1999[Sheldon, P. J., Mao, Y., He, M. & Sherman, D. H. (1999). J. Bacteriol. 181, 2507-2512.]); Danshiitsoodol et al. (2006[Danshiitsoodol, N., de Pinho, C. A., Matoba, Y., Kumagai, T. & Sugiyama, M. (2006). J. Mol. Biol. 360, 398-408.]); Vicik et al. (2006[Vicik, R., Hoerr, V., Glaser, M., Schultheis, M., Hansell, E., Mckerrow, J. H., Holzgrabe, U., Caffrey, C. R., Ponte-Sucre, A., Moll, H., Stich, A. & Schirmeister, T. (2006). Bioorg. Med. Chem. Lett. 16, 2753-2757.]); Keniche et al. (2011[Keniche, A., Mezrai, A. & Mulengi, J. K. (2011). Open Conf. Proc. J. 2, 28-35.]); Lee et al. (1992[Lee, C. S., Hartley, J. A., Berardini, M. D., Butler, J., Siegel, D., Ross, D. & Gibson, N. W. (1992). Biochemistry, 31, 3019-3025.]); Ngo et al. (1998[Ngo, E. O., Nutter, L. M., Sura, T. & Gutierrez, P. L. (1998). Chem. Res. Toxicol. 11, 360-368.]). For the use of chiral aziridines as precursors for pharmaceutical products, see: Kim et al. (2001[Kim, B. M., Bae, S. J., So, S. M., Yoo, H. T., Chang, S. K., Lee, J. H. & Kang, J. (2001). Org. Lett. 3, 2349-2351.]). For related structures, see: Zhu et al. (2006[Zhu, J., Zhang, M.-J., Liu, Q.-W. & Pan, Z.-H. (2006). Acta Cryst. E62, o1507-o1508.]). For details of the synthesis, see: Madesclaire et al. (2013[Madesclaire, M., Coudert, P., Leal, F., Tarrit, S., Zaitseva, J. V. & Zaitsev, V. P. (2013). Chem. Heterocycl. Compd. In preparation.]). For determination of the absolute configuration, see: Hooft et al. (2008[Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.]).

[Scheme 1]

Experimental

Crystal data
  • C9H10N2O3·H2O

  • Mr = 212.21

  • Monoclinic, P 21

  • a = 6.3064 (2) Å

  • b = 5.4695 (2) Å

  • c = 14.6481 (5) Å

  • [beta] = 94.303 (2)°

  • V = 503.83 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.68 × 0.44 × 0.06 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.944, Tmax = 1.000

  • 5357 measured reflections

  • 2383 independent reflections

  • 2031 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.086

  • S = 1.04

  • 2383 reflections

  • 152 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O5i 0.91 (2) 2.24 (2) 3.064 (2) 150.0 (19)
O5-H5...O1Wii 0.798 (19) 2.03 (2) 2.8303 (19) 175.0 (17)
O1W-H1W...N1 0.90 (2) 1.89 (2) 2.772 (2) 167 (2)
O1W-H2W...O1Wiii 0.90 (2) 2.00 (2) 2.8971 (9) 172 (3)
Symmetry codes: (i) x, y-1, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iii) [-x+2, y-{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2453 ).


References

Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Danshiitsoodol, N., de Pinho, C. A., Matoba, Y., Kumagai, T. & Sugiyama, M. (2006). J. Mol. Biol. 360, 398-408.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.  [ISI] [CrossRef] [ChemPort] [details]
Keniche, A., Mezrai, A. & Mulengi, J. K. (2011). Open Conf. Proc. J. 2, 28-35.  [CrossRef] [ChemPort]
Kim, B. M., Bae, S. J., So, S. M., Yoo, H. T., Chang, S. K., Lee, J. H. & Kang, J. (2001). Org. Lett. 3, 2349-2351.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lee, C. S., Hartley, J. A., Berardini, M. D., Butler, J., Siegel, D., Ross, D. & Gibson, N. W. (1992). Biochemistry, 31, 3019-3025.  [CrossRef] [PubMed] [ChemPort] [ISI]
Li, V., Choi, D., Tang, M. & Kohn, H. (1995). J. Biochem. 34, 7120-7126.  [ChemPort]
Madesclaire, M., Coudert, P., Leal, F., Tarrit, S., Zaitseva, J. V. & Zaitsev, V. P. (2013). Chem. Heterocycl. Compd. In preparation.
Ngo, E. O., Nutter, L. M., Sura, T. & Gutierrez, P. L. (1998). Chem. Res. Toxicol. 11, 360-368.  [CrossRef] [ChemPort] [PubMed]
Sheldon, P. J., Mao, Y., He, M. & Sherman, D. H. (1999). J. Bacteriol. 181, 2507-2512.  [ISI] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Vicik, R., Hoerr, V., Glaser, M., Schultheis, M., Hansell, E., Mckerrow, J. H., Holzgrabe, U., Caffrey, C. R., Ponte-Sucre, A., Moll, H., Stich, A. & Schirmeister, T. (2006). Bioorg. Med. Chem. Lett. 16, 2753-2757.  [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhu, J., Zhang, M.-J., Liu, Q.-W. & Pan, Z.-H. (2006). Acta Cryst. E62, o1507-o1508.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o927  [ doi:10.1107/S1600536813013391 ]

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