2-Bromo-4-(3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-6-meth­oxy­phenol

Hariono, M.; Ngah, N.; Wahab, H.A.; Abdul Rahim, A.S.

doi:10.1107/S1600536811051269

Volume 68
Part 1
Pages o35-o36
January 2012

Received 24 November 2011
Accepted 29 November 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.023
wR = 0.056
Data-to-parameter ratio = 14.3
Details

2-Bromo-4-(3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-6-methoxyphenol

Maywan Hariono,^a Nurziana Ngah,^b Habibah A. Wahab ^a and Aisyah Saad Abdul Rahim ^a ^*

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM Penang, Malaysia, and ^bKulliyyah of Science, International Islamic University Malaysia, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia
Correspondence e-mail: aisyah@usm.my

In the title compound, C₁₈H₂₀BrNO₃, the oxazolidine ring adopts an envelope conformation with the N atom at the flap position. The mean plane of oxazolidine ring makes dihedral angles of 82.96 (13) and 70.97 (12)°, respectively, with the phenyl and benzene rings. In the crystal, adjacent molecules are connected via O-HO and C-HO hydrogen bonds and C-H [pi] interactions into a zigzag chain along the b axis.

Related literature

For the synthesis and closely related structures, see: Asaruddin et al. (2010); Diwischeck et al. (2003); Khruscheva et al. (1997); Duffy et al. (2004). For therapeutic properties of oxazolidine derivatives, see: Moloney et al. (1998); Wang et al. (2010); Nakano et al. (2010); Fülöp et al. (2004); Panneerselvam (2011). For standard bond lengths, see: Allen et al. (1987). For the low-temperature device used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₈H₂₀BrNO₃
M_r = 378.26
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.8056 (4) Å
b = 11.9034 (6) Å
c = 18.9109 (9) Å
V = 1757.07 (15) Å³
Z = 4
Mo K radiation
= 2.35 mm^-1
T = 100 K
0.50 × 0.36 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.383, T_max = 0.618
10569 measured reflections
3074 independent reflections
2935 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.023
wR(F²) = 0.056
S = 1.08
3074 reflections
215 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.32 e Å^-3
_min = -0.26 e Å^-3
Absolute structure: Flack (1983), 1283 Friedel pairs
Flack parameter: 0.004 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1-C6 phenyl ring.

D-HA	D-H	HA	DA	D-HA
O2-H2O1ⁱ	0.85 (1)	2.03 (1)	2.7853 (19)	148 (2)
C15-H15AO2ⁱⁱ	0.95	2.46	3.232 (3)	138
C18-H18ACg2ⁱ	0.98	2.96	3.679 (3)	131
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5016 ).

Acknowledgements

MH, HAW and ASAR acknowledge the Malaysia Ministry of Science, Technology and Innovations (MOSTI) for funding the synthetic chemistry work under the R&D initiative grant Nos. 09-05-lfn-meb-004 and 304/PFARMASI/650544/I121. MH thanks Universiti Sains Malaysia for the award of a postgraduate fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Asaruddin, M. R., Wahab, H. A., Mohamed, N., Goh, J. H. & Fun, H.-K. (2010). Acta Cryst. E66, o1452-o1453.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Diwischeck, F., Heller, E. & Holzgrabe, U. (2003). Monatsh. Chem. 134, 1105-1111.
Duffy, M., Gallagher, J. F. & Lough, A. J. (2004). Acta Cryst. E60, o234-o236.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Fülöp, F., Lázár, L., Szakonyi, Z., Pihlavisto, M., Alaranta, S., Vainio, P. J., Juhakoski, A., Marjamäki, M. & Smith, D. J. (2004). Pure Appl. Chem. 76, 965-972.
Khruscheva, N. S., Loim, N. M., Sokolov, V. I. & Makhaev, V. D. (1997). J. Chem. Soc. Perkin Trans. 1, pp. 2425-2427.
Moloney, G. P., Craik, D. J., Iskander, M. N. & Nero, T. L. (1998). J. Chem. Soc. Perkin Trans. 2, pp. 199-206.
Nakano, H., Osone, K., Takeshita, M., Kwon, E., Seki, C., Matsuyama, H., Takano, N. & Kohari, Y. (2010). Chem. Commun. 46, 4827-4829.
Panneerselvam, T. (2011). J. Adv. Pharm. Tech. Res. 2, 43-46.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
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organic compounds