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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 [sigma](C-C) = 0.003 Å
R = 0.023
wR = 0.056
Data-to-parameter ratio = 14.3
Details
Open access

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

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-H...O and C-H...O 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[Asaruddin, M. R., Wahab, H. A., Mohamed, N., Goh, J. H. & Fun, H.-K. (2010). Acta Cryst. E66, o1452-o1453.]); Diwischeck et al. (2003[Diwischeck, F., Heller, E. & Holzgrabe, U. (2003). Monatsh. Chem. 134, 1105-1111.]); Khruscheva et al. (1997[Khruscheva, N. S., Loim, N. M., Sokolov, V. I. & Makhaev, V. D. (1997). J. Chem. Soc. Perkin Trans. 1, pp. 2425-2427.]); Duffy et al. (2004[Duffy, M., Gallagher, J. F. & Lough, A. J. (2004). Acta Cryst. E60, o234-o236.]). For therapeutic properties of oxazolidine derivatives, see: Moloney et al. (1998[Moloney, G. P., Craik, D. J., Iskander, M. N. & Nero, T. L. (1998). J. Chem. Soc. Perkin Trans. 2, pp. 199-206.]); Wang et al. (2010[Wang, Y., Chan, C., Su, Z. & Chen, C. (2010). Biophys. Chem. 147, 74-80.]); Nakano et al. (2010[Nakano, H., Osone, K., Takeshita, M., Kwon, E., Seki, C., Matsuyama, H., Takano, N. & Kohari, Y. (2010). Chem. Commun. 46, 4827-4829.]); Fülöp et al. (2004[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.]); Panneerselvam (2011[Panneerselvam, T. (2011). J. Adv. Pharm. Tech. Res. 2, 43-46.]). For standard bond lengths, see: Allen et al. (1987[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.]). For the low-temperature device used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C18H20BrNO3

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.383, Tmax = 0.618

  • 10569 measured reflections

  • 3074 independent reflections

  • 2935 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 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-H...A D-H H...A D...A D-H...A
O2-H2...O1i 0.85 (1) 2.03 (1) 2.7853 (19) 148 (2)
C15-H15A...O2ii 0.95 2.46 3.232 (3) 138
C18-H18A...Cg2i 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CSD] [CrossRef] [details]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
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.  [CSD] [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
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.  [CrossRef]
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.  [CrossRef] [ChemPort]
Panneerselvam, T. (2011). J. Adv. Pharm. Tech. Res. 2, 43-46.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wang, Y., Chan, C., Su, Z. & Chen, C. (2010). Biophys. Chem. 147, 74-80.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o35-o36   [ doi:10.1107/S1600536811051269 ]

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