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

Mansor, N.S.; Mohammat, M.F.; Shaameri, Z.; Khaledi, H.

doi:10.1107/S1600536813001943

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 (C-C) = 0.002 Å
R = 0.039
wR = 0.104
Data-to-parameter ratio = 14.4
Details

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

Nurul Shulehaf Mansor,^a Mohd Fazli Mohammat,^a Zurina Shaameri ^a and Hamid Khaledi ^b ^*

^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-HO hydrogen bonds, forming a layer parallel to the ab plane. The two-dimensional network is further stabilized by intermolecular C-HO hydrogen bonds.

Related literature

For the structures of similar compounds, see: Ma & Jiang (1998); Chu et al. (2011); Gainsford & Mason (2010). For the synthesis of the precursor substituted 2,5-dihydropyrrole-2-one, see: Mohammat et al. (2009).

Experimental

Crystal data

C₁₄H₁₇NO₄·1.25H₂O
M_r = 285.81
Triclinic, $[P \overline 1]$
a = 10.3669 (2) Å
b = 15.7466 (3) Å
c = 18.4539 (3) Å
= 77.373 (1)°
= 80.425 (1)°
= 87.058 (1)°
V = 2898.31 (9) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.979, T_max = 0.991
22505 measured reflections
11260 independent reflections
9637 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(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
_max = 0.75 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2A-H2AO5	0.81 (2)	1.86 (2)	2.6569 (16)	166 (2)
O2B-H2BO1Bⁱ	0.84 (1)	1.89 (2)	2.7111 (14)	165 (2)
O2C-H2CO1Cⁱⁱ	0.85 (1)	1.89 (2)	2.7089 (14)	162 (2)
O2D-H2DO8ⁱⁱⁱ	0.82 (2)	1.92 (2)	2.7134 (17)	164 (2)
O5-H5EO1Cⁱⁱ	0.86 (1)	1.94 (2)	2.7857 (15)	168 (2)
O5-H5FO2Dⁱⁱⁱ	0.86 (1)	1.79 (1)	2.6490 (17)	178 (2)
O6-H6FO2C^iv	0.90 (1)	1.99 (1)	2.8837 (16)	177 (2)
O6-H6EO1Dⁱⁱⁱ	0.88 (1)	1.96 (2)	2.8218 (15)	167 (2)
O7-H7FO1A	0.87 (1)	1.97 (2)	2.8399 (16)	176 (2)
O7-H7EO2B^v	0.89 (1)	2.01 (1)	2.8987 (16)	175 (2)
O8-H8EO7	0.95 (2)	1.87 (2)	2.7637 (18)	156 (2)
O8-H8FO9	0.91 (1)	1.93 (2)	2.8193 (18)	168 (2)
O9-H9FO2A	0.84 (2)	1.98 (2)	2.8199 (17)	176 (2)
O9-H9EO6	0.90 (1)	1.93 (2)	2.7724 (18)	155 (2)
C3B-H3BO1A^vi	1.00	2.45	3.2581 (17)	138
C3C-H3CO1D	1.00	2.31	3.1537 (17)	142
C3D-H3DO1Dⁱⁱⁱ	1.00	2.56	3.4252 (18)	145
C5A-H5AO7^v	1.00	2.34	3.2374 (18)	148
C5B-H5BO9^vi	1.00	2.40	3.2568 (19)	143
C5C-H5CO8ⁱⁱⁱ	1.00	2.49	3.2395 (19)	131
C5D-H5DO6	1.00	2.41	3.2010 (18)	135
C7A-H7AO3B	0.95	2.38	3.2943 (17)	162
C7B-H7BO3A^vi	0.95	2.46	3.3253 (18)	151
C7C-H7CO3D	0.95	2.39	3.2704 (18)	155
C11A-H11AO4B^iv	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).

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.
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.
Gainsford, G. J. & Mason, J. M. (2010). Acta Cryst. E66, o957.
Ma, D. & Jiang, J. (1998). Tetrahedron Asymmetry, 9, 575-579.
Mohammat, M. F., Shaameri, Z. & Hamzah, A. S. (2009). Molecules, 14, 250-256.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds