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

Maywan Hariono; Nurziana Ngah; Habibah A Wahab; Aisyah Saad Abdul Rahim

doi:10.1107/S1600536811051269

. 2011 Dec 7;68(Pt 1):o35–o36. doi: 10.1107/S1600536811051269

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, Aisyah Saad Abdul Rahim ^a,^*

PMCID: PMC3254397 PMID: 22259539

Abstract

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⋯π 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,
a = 7.8056 (4) Å
b = 11.9034 (6) Å
c = 18.9109 (9) Å
V = 1757.07 (15) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.037

Refinement

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

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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051269/is5016sup1.cif

e-68-00o35-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051269/is5016Isup2.hkl

e-68-00o35-Isup2.hkl^{(150.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811051269/is5016Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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.

supplementary crystallographic information

Comment

Oxazolidine compounds are important in understanding drug behaviour in medicinal chemistry (Duffy et al., 2004). Derivatives of oxazolidine have shown inhibitory effects for several diseases or condition such as β-adrenoreseptor antagonist (Moloney et al., 1998), influenza antiviral (Wang et al., 2010; Nakano et al., 2010), antinflammatory agents (Fulop et al., 2004) and antihyperglycemic (Panneerselvam, 2011). In this paper, we report the X-ray crystal structure of the title oxazolidine compound, (I).

The title compound, C₁₈H₂₀BrNO₃, consists of two aromatic rings which are connected through oxazolidine ring (Fig. 1). The molecule is similar with those reported by Asaruddin et al. (2010), in that only the present of Br atom at β position of 3-hydroxy-4-methoxyphenyl ring is different. The oxazolidine ring (O1/C7–C9/N1) adopts an envelope conformation with puckering parameters of Q = 0.433 (2) Å and φ = 107.3 (3)°. The N1 atom is at the flap position and it deviates from the mean plane through the remaining four atoms by 0.651 (2) Å. The C1–C6 phenyl and C10–C15 benzene rings make dihedral angles of 82.96 (13) and 70.97 (12)°, respectively, with the mean plane of oxazolidine ring. The bond lengths and angles are in normal ranges (Allen et al., 1987) and in agreement with those reported by Asaruddin et al. (2010).

In the crystal structure, adjacent molecules are connected via intermolecular O2—H2···O1 and C15—H15A···O2 hydrogen bonds and C18—H18A···Cg2 interactions (Table 1) to form a chain along the [010] direction; Cg2 is the centroid of the C1–C6 ring.

Experimental

Following a modified method (Asaruddin et al., 2010; Diwischeck et al., 2003; Khruscheva et al., 1997), (1S,2S)-2-methylamino-1-phenylpropan-1-ol (0.17 g, 1 mmol) was mixed with 3-bromo-4-hydroxy-5-methoxybenzaldehyde (0.23 g, 1 mmol) in a two-round neck bottom flask. The mixture was dissolved in methanol (4 ml) and molecular sieve 4Å (0.1 g) was added to the reaction mixture then the solution was refluxed at 333 K for 6 h. The solution was filtered and the solvent was evaporated in vacuo to give a crude product which was then recrystallized three times from methanol to give colourless blocks with a yield 11%. These were washed with n-hexane and dried overnight to afford single crystals suitable for X-ray analysis.