(IUCr) 4-Hydroxy-5-(4-methoxyphenyl)pyrrolidin-2-one

Volume 64
Part 3
Pages o578-o579
March 2008

Received 4 February 2008
Accepted 6 February 2008
Online 13 February 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.110
Data-to-parameter ratio = 10.8
Details

4-Hydroxy-5-(4-methoxyphenyl)pyrrolidin-2-one

M. Fazli Mohammat,^a Zurina Shaameri,^a A. Sazali Hamzah,^a Hoong-Kun Fun ^b ^* and Suchada Chantrapromma ^c ⁺

^aInstitute of Science, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia,^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: hkfun@usm.my

In the title compound, C₁₁H₁₃NO₃, the pyrrolidin-2-one ring is in an envelope conformation with the hydroxyl and 4-methoxyphenyl substituents mutually cis. The methoxy group is slighty twisted away from the mean plane of the attached benzene ring. The molecules are arranged into screw chains along the c axis. These chains are interconnected via intermolecular O-HO and N-HO hydrogen bonds into sheets parallel to the ac plane. The crystal structure is further stabilized by weak intermolecular C-HO and C-H [pi] interactions.

Related literature

For details of ring conformations, see: Cremer & Pople (1975). For the biological properties of pyrrolidine alkaloids, see for example: Iida et al. (1986); Royles (1996). For the syntheses of compounds containing the tetramic acid ring, see for example: Chandrasekhar et al. (2006); Gurjar et al. (2006); Yoda et al. (1996). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₁H₁₃NO₃
M_r = 207.22
Orthorhombic, P c a 2₁
a = 11.9862 (6) Å
b = 11.6251 (6) Å
c = 7.1539 (4) Å
V = 996.83 (9) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 100.0 (1) K
0.43 × 0.20 × 0.17 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.958, T_max = 0.983
8681 measured reflections
1562 independent reflections
1218 reflections with I > 2(I)
R_int = 0.066

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.109
S = 1.09
1562 reflections
145 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5-C10 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1N1O2ⁱ	0.88 (4)	2.05 (4)	2.917 (3)	167 (4)
O2-H1O2O3ⁱⁱ	0.90 (4)	1.98 (4)	2.800 (2)	152 (3)
C3-H3AO1ⁱⁱⁱ	0.98	2.33	3.193 (3)	146
C11-H11AO1^iv	0.96	2.49	3.395 (3)	158
C6-H6ACg1^v	0.93	2.81	3.514 (3)	133
C9-H9ACg1^vi	0.93	2.68	3.554 (3)	157
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) $[-x+2, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+2, z]$ ; (iv) $[-x+{\script{3\over 2}}, y-1, z-{\script{1\over 2}}]$ ; (v) $[x+{\script{3\over 2}}, -y, z]$ ; (vi) $[-x+2, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2463 ).

Acknowledgements

The authors acknowledge the generous support of both the Universiti Teknologi MARA and Universiti Sains Malaysia as well as the financial support of the Ministry of Science, Technology and Innovation (E-Science grant No. SF0050-02-01-01). HKF and SC thank the Malaysian Government and Universiti Sains Malaysia for the Scientific Advancement Grant Allocation (SAGA) grant No. 304/PFIZIK/653003/A118.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chandrasekhar, S., Saritha, B., Jagadeshwar, V. & Prakash, S. J. (2006). Tetrahedron Asymmetry, 17, 1380-1386.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Gurjar, M. K., Borhade, R. G., Puranik, V. G. & Ramana, C. V. (2006). Tetrahedron Lett., 47, 6979-6981.
Iida, H., Yamazaki, N. & Kibayashi, C. (1986). Tetrahedron Lett. 27, 5393-5396.
Royles, B. J. L. (1996). Chem. Rev. 95, 1961-2001.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Yoda, H., Nakajima, T. & Takabe, K. (1996). Tetrahedron Lett. 31, 5531-5534.

organic compounds