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Volume 69 
Part 2 
Pages o293-o294  
February 2013  

Received 14 January 2013
Accepted 19 January 2013
Online 26 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.104
Data-to-parameter ratio = 14.4
Details
Open access

Ethyl 4-hydroxy-1-methyl-5-oxo-2-phenylpyrrolidine-3-carboxylate 1.25-hydrate

aOrganic Synthesis Labratory, Institute of Science, Universiti Tecknologi MARA, 40450 Shah Alam, Selangor, Malaysia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: hamid.khaledi@gmail.com

The asymmetric unit of the title compound, C14H17NO4·1.25H2O, consists of four substituted pyrrolidone molecules (two pairs of enantiomers) and five water molecules. The five-membered rings each have an envelope conformation, with the C atom bonded to the ester group as the flap. The mean planes of the five-membered rings of the four pyrrolidone molecules make dihedral angles of 60.87 (5), 64.45 (5), 62.03 (5) and 65.79 (5)° with respect to the phenyl rings. In the crystal, the pyrrolidone and water molecules are connected through O-H...O hydrogen bonds, forming a layer parallel to the ab plane. The two-dimensional network is further stabilized by intermolecular C-H...O hydrogen bonds.

Related literature

For the structures of similar compounds, see: Ma & Jiang (1998[Ma, D. & Jiang, J. (1998). Tetrahedron Asymmetry, 9, 575-579.]); Chu et al. (2011[Chu, A. M., Fettinger, J. C. & David, S. S. (2011). Bioorg. Med. Chem. Lett. 21, 4969-4972.]); Gainsford & Mason (2010[Gainsford, G. J. & Mason, J. M. (2010). Acta Cryst. E66, o957.]). For the synthesis of the precursor substituted 2,5-dihydropyrrole-2-one, see: Mohammat et al. (2009[Mohammat, M. F., Shaameri, Z. & Hamzah, A. S. (2009). Molecules, 14, 250-256.]).

[Scheme 1]

Experimental

Crystal data
  • C14H17NO4·1.25H2O

  • Mr = 285.81

  • Triclinic, [P \overline 1]

  • a = 10.3669 (2) Å

  • b = 15.7466 (3) Å

  • c = 18.4539 (3) Å

  • [alpha] = 77.373 (1)°

  • [beta] = 80.425 (1)°

  • [gamma] = 87.058 (1)°

  • V = 2898.31 (9) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.21 × 0.15 × 0.09 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.979, Tmax = 0.991

  • 22505 measured reflections

  • 11260 independent reflections

  • 9637 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.104

  • S = 1.02

  • 11260 reflections

  • 780 parameters

  • 20 restraints

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

  • [Delta][rho]max = 0.75 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2A-H2A...O5 0.81 (2) 1.86 (2) 2.6569 (16) 166 (2)
O2B-H2B...O1Bi 0.84 (1) 1.89 (2) 2.7111 (14) 165 (2)
O2C-H2C...O1Cii 0.85 (1) 1.89 (2) 2.7089 (14) 162 (2)
O2D-H2D...O8iii 0.82 (2) 1.92 (2) 2.7134 (17) 164 (2)
O5-H5E...O1Cii 0.86 (1) 1.94 (2) 2.7857 (15) 168 (2)
O5-H5F...O2Diii 0.86 (1) 1.79 (1) 2.6490 (17) 178 (2)
O6-H6F...O2Civ 0.90 (1) 1.99 (1) 2.8837 (16) 177 (2)
O6-H6E...O1Diii 0.88 (1) 1.96 (2) 2.8218 (15) 167 (2)
O7-H7F...O1A 0.87 (1) 1.97 (2) 2.8399 (16) 176 (2)
O7-H7E...O2Bv 0.89 (1) 2.01 (1) 2.8987 (16) 175 (2)
O8-H8E...O7 0.95 (2) 1.87 (2) 2.7637 (18) 156 (2)
O8-H8F...O9 0.91 (1) 1.93 (2) 2.8193 (18) 168 (2)
O9-H9F...O2A 0.84 (2) 1.98 (2) 2.8199 (17) 176 (2)
O9-H9E...O6 0.90 (1) 1.93 (2) 2.7724 (18) 155 (2)
C3B-H3B...O1Avi 1.00 2.45 3.2581 (17) 138
C3C-H3C...O1D 1.00 2.31 3.1537 (17) 142
C3D-H3D...O1Diii 1.00 2.56 3.4252 (18) 145
C5A-H5A...O7v 1.00 2.34 3.2374 (18) 148
C5B-H5B...O9vi 1.00 2.40 3.2568 (19) 143
C5C-H5C...O8iii 1.00 2.49 3.2395 (19) 131
C5D-H5D...O6 1.00 2.41 3.2010 (18) 135
C7A-H7A...O3B 0.95 2.38 3.2943 (17) 162
C7B-H7B...O3Avi 0.95 2.46 3.3253 (18) 151
C7C-H7C...O3D 0.95 2.39 3.2704 (18) 155
C11A-H11A...O4Biv 0.95 2.54 3.3027 (17) 138
Symmetry codes: (i) -x, -y, -z+1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) x+1, y, z; (v) -x+1, -y, -z+1; (vi) x-1, y, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: SHELXL97 and 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: IS5239 ).


Acknowledgements

The authors acknowledge the generous support of Universiti Teknologi MARA Malaysia (FRGS grant No. 600-RMI/ST/FRGS 5/3/Fst (11/2008) and the University of Malaya.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chu, A. M., Fettinger, J. C. & David, S. S. (2011). Bioorg. Med. Chem. Lett. 21, 4969-4972.  [CSD] [CrossRef] [ChemPort] [PubMed]
Gainsford, G. J. & Mason, J. M. (2010). Acta Cryst. E66, o957.  [CrossRef] [details]
Ma, D. & Jiang, J. (1998). Tetrahedron Asymmetry, 9, 575-579.  [ISI] [CrossRef] [ChemPort]
Mohammat, M. F., Shaameri, Z. & Hamzah, A. S. (2009). Molecules, 14, 250-256.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o293-o294   [ doi:10.1107/S1600536813001943 ]

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