Hariono, Maywan

Acta Crystallographica Section E

Repository Universitas Sanata Dharma

2-Bromo-4-(3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-6-methoxyphenolMaywan Hariono,a Nurziana Ngah,b Habibah A. Wahabaand Aisyah Saad Abdul Rahima*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, MalaysiaCorrespondence e-mail: aisyah@usm.myReceived 24 November 2011; accepted 29 November 2011Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.003 A˚;R factor = 0.023; wR factor = 0.056; data-to-parameter ratio = 14.3.In the title compound, C18H20BrNO3, the oxazolidine ringadopts an envelope conformation with the N atom at the flapposition. The mean plane of oxazolidine ring makes dihedralangles of 82.96 (13) and 70.97 (12), respectively, with thephenyl and benzene rings. In the crystal, adjacent moleculesare connected via O—H  O and C—H  O hydrogen bondsand C—H   interactions into a zigzag chain along the b axis.Related literatureFor the synthesis and closely related structures, see: Asaruddinet al. (2010); Diwischeck et al. (2003); Khruscheva et al. (1997);Duffy et al. (2004). For therapeutic properties of oxazolidinederivatives, see: Moloney et al. (1998); Wang et al. (2010);Nakano et al. (2010); Fu¨lo¨p et al. (2004); Panneerselvam(2011). For standard bond lengths, see: Allen et al. (1987). Forthe low-temperature device used in the data collection, see:Cosier & Glazer (1986).ExperimentalCrystal dataC18H20BrNO3Mr = 378.26Orthorhombic, P212121a = 7.8056 (4) A˚b = 11.9034 (6) A˚c = 18.9109 (9) A˚V = 1757.07 (15) A˚3Z = 4Mo K radiation = 2.35 mm1T = 100 K0.50  0.36  0.23 mmData collectionBruker SMART APEXII CCDarea-detector diffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2009)Tmin = 0.383, Tmax = 0.61810569 measured reflections3074 independent reflections2935 reflections with I > 2(I)Rint = 0.037RefinementR[F 2 > 2(F 2)] = 0.023wR(F 2) = 0.056S = 1.083074 reflections215 parameters1 restraintH atoms treated by a mixture ofindependent and constrainedrefinementmax = 0.32 e A˚3min = 0.26 e A˚3Absolute structure: Flack (1983),1283 Friedel pairsFlack parameter: 0.004 (7)Table 1Hydrogen-bond geometry (A˚, ).Cg2 is the centroid of the C1–C6 phenyl ring.D—H  A D—H H  A D  A D—H  AO2—H2  O1i 0.85 (1) 2.03 (1) 2.7853 (19) 148 (2)C15—H15A  O2ii 0.95 2.46 3.232 (3) 138C18—H18A  Cg2i 0.98 2.96 3.679 (3) 131Symmetry codes: (i) xþ 1; yþ 12;zþ 32; (ii) xþ 1; y  12;zþ 32.Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT(Bruker, 2009); data reduction: SAINT; program(s) used to solvestructure: SHELXTL (Sheldrick, 2008); program(s) used to refinestructure: SHELXTL; molecular graphics: SHELXTL; software usedto prepare material for publication: SHELXTL and PLATON (Spek,2009).MH, HAW and ASAR acknowledge the Malaysia Ministryof Science, Technology and Innovations (MOSTI) for fundingthe synthetic chemistry work under the R&D initiative grantNos. 09-05-lfn-meb-004 and 304/PFARMASI/650544/I121.MH thanks Universiti Sains Malaysia for the award of apostgraduate fellowship.Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: IS5016).ReferencesAllen, 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.Fu¨lo¨p, F., La´za´r, L., Szakonyi, Z., Pihlavisto, M., Alaranta, S., Vainio, P. J.,Juhakoski, A., Marjama¨ki, 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.organic compoundsActa Cryst. (2012). E68, o35–o36 doi:10.1107/S1600536811051269 Hariono et al. o35Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368Nakano, 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.Wang, Y., Chan, C., Su, Z. & Chen, C. (2010). Biophys. Chem. 147, 74–80.organic compoundso36 Hariono et al.  C18H20BrNO3 Acta Cryst. (2012). E68, o35–o36supporting informationsup-1Acta Cryst. (2012). E68, o35–o36    supporting informationActa Cryst. (2012). E68, o35–o36    [doi:10.1107/S1600536811051269]2-Bromo-4-(3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-6-methoxyphenolMaywan Hariono, Nurziana Ngah, Habibah A. Wahab and Aisyah Saad Abdul RahimS1. 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.S2. 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.S3. Refinement X-ray data were collected at 100 K (Cosier & Glazer, 1986). The hydroxyl H atom was located in a difference map and refined freely [O2—H2 = 0.8499 (10) Å]. Other H atoms were positioned geometrically and refined using riding model with C—H = 0.95–1.00 Å and Uiso(H)=1.2 or 1.5Ueq(C). A rotating group model was applied for methyl group.supporting informationsup-2Acta Cryst. (2012). E68, o35–o36    Figure 1The molecular structure of the title compound, with displacement ellipsoids are drawn at the 50% probability level. supporting informationsup-3Acta Cryst. (2012). E68, o35–o36    Figure 2The molecular packing of the title compound viewed down the a axis. 2-Bromo-4-(3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-6-methoxyphenol Crystal data C18H20BrNO3Mr = 378.26Orthorhombic, P212121Hall symbol: P 2ac 2aba = 7.8056 (4) Åb = 11.9034 (6) Åc = 18.9109 (9) ÅV = 1757.07 (15) Å3Z = 4F(000) = 776Dx = 1.430 Mg m−3Mo Kα radiation, λ = 0.71073 ÅCell parameters from 8965 reflectionsθ = 2.0–24.9°µ = 2.35 mm−1T = 100 KBlock, colourless0.50 × 0.36 × 0.23 mmsupporting informationsup-4Acta Cryst. (2012). E68, o35–o36    Data collection Bruker SMART APEXII CCD area-detector diffractometerRadiation source: fine-focus sealed tubeGraphite monochromatorDetector resolution: 83.66 pixels mm-1φ and ω scanAbsorption correction: multi-scan (SADABS; Bruker, 2009)Tmin = 0.383, Tmax = 0.61810569 measured reflections3074 independent reflections2935 reflections with I > 2σ(I)Rint = 0.037θmax = 24.9°, θmin = 2.0°h = −9→9k = −14→14l = −22→22Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.023wR(F2) = 0.056S = 1.083074 reflections215 parameters1 restraintPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapHydrogen site location: inferred from neighbouring sitesH atoms treated by a mixture of independent and constrained refinementw = 1/[σ2(Fo2) + (0.0197P)2] where P = (Fo2 + 2Fc2)/3(Δ/σ)max = 0.001Δρmax = 0.32 e Å−3Δρmin = −0.26 e Å−3Absolute structure: Flack (1983), 1283 Friedel pairsAbsolute structure parameter: 0.004 (7)Special details Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open=flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/UeqBr1 0.58037 (3) 0.865565 (17) 0.942297 (10) 0.02402 (8)O1 0.2217 (2) 0.40943 (12) 0.84900 (7) 0.0161 (3)O2 0.6507 (2) 0.85865 (13) 0.78478 (7) 0.0187 (3)O3 0.5513 (2) 0.71024 (11) 0.68917 (7) 0.0195 (3)N1 0.0154 (3) 0.54199 (15) 0.83295 (9) 0.0179 (4)C1 0.0051 (3) 0.1430 (2) 0.85221 (12) 0.0259 (5)H1A −0.0140 0.1381 0.8027 0.031*C2 −0.0108 (4) 0.0473 (2) 0.89404 (16) 0.0362 (7)H2A −0.0416 −0.0224 0.8732 0.043*C3 0.0182 (4) 0.0542 (2) 0.96587 (14) 0.0365 (7)H3A 0.0072 −0.0110 0.9944 0.044*C4 0.0633 (4) 0.1557 (2) 0.99672 (12) 0.0341 (6)supporting informationsup-5Acta Cryst. (2012). E68, o35–o36    H4A 0.0831 0.1600 1.0462 0.041*C5 0.0792 (4) 0.25110 (19) 0.95494 (11) 0.0257 (5)H5A 0.1110 0.3205 0.9760 0.031*C6 0.0490 (3) 0.24580 (18) 0.88251 (10) 0.0191 (5)C7 0.0610 (3) 0.34994 (17) 0.83700 (10) 0.0170 (5)H7A 0.0563 0.3265 0.7862 0.020*C8 0.1793 (3) 0.52295 (17) 0.86771 (10) 0.0165 (5)H8A 0.1630 0.5277 0.9201 0.020*C9 −0.0781 (3) 0.43775 (18) 0.84969 (10) 0.0191 (5)H9A −0.1098 0.4379 0.9009 0.023*C10 0.3140 (3) 0.60567 (17) 0.84574 (10) 0.0152 (5)C11 0.3775 (3) 0.68157 (17) 0.89478 (11) 0.0167 (5)H11A 0.3434 0.6764 0.9429 0.020*C12 0.4899 (3) 0.76443 (18) 0.87389 (10) 0.0162 (5)C13 0.5436 (3) 0.77558 (17) 0.80434 (10) 0.0153 (4)C14 0.4837 (3) 0.69524 (17) 0.75520 (10) 0.0149 (4)C15 0.3686 (3) 0.61278 (17) 0.77486 (10) 0.0153 (4)H15A 0.3264 0.5611 0.7407 0.018*C16 −0.2384 (3) 0.4204 (2) 0.80546 (13) 0.0302 (6)H16A −0.3266 0.4741 0.8202 0.045*H16B −0.2808 0.3437 0.8122 0.045*H16C −0.2112 0.4324 0.7554 0.045*C17 −0.0712 (3) 0.64373 (18) 0.85614 (11) 0.0258 (5)H17A 0.0013 0.7090 0.8461 0.039*H17B −0.0931 0.6394 0.9071 0.039*H17C −0.1802 0.6513 0.8309 0.039*C18 0.5220 (3) 0.62188 (19) 0.63849 (10) 0.0224 (5)H18A 0.5904 0.6361 0.5960 0.034*H18B 0.4003 0.6199 0.6259 0.034*H18C 0.5554 0.5496 0.6591 0.034*H2 0.659 (3) 0.856 (2) 0.74000 (15) 0.022 (6)*Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23Br1 0.03139 (14) 0.02299 (12) 0.01767 (10) −0.00772 (11) −0.00524 (10) −0.00103 (8)O1 0.0127 (8) 0.0156 (7) 0.0200 (7) −0.0001 (7) 0.0011 (6) 0.0004 (5)O2 0.0203 (8) 0.0183 (8) 0.0176 (7) −0.0032 (7) 0.0025 (6) 0.0005 (6)O3 0.0228 (10) 0.0188 (8) 0.0171 (6) −0.0038 (7) 0.0049 (7) −0.0016 (5)N1 0.0126 (10) 0.0177 (10) 0.0234 (8) −0.0018 (8) −0.0014 (8) 0.0019 (7)C1 0.0216 (13) 0.0234 (12) 0.0328 (11) −0.0021 (11) −0.0001 (10) −0.0009 (10)C2 0.0318 (16) 0.0194 (13) 0.0574 (16) −0.0070 (12) 0.0011 (14) 0.0022 (11)C3 0.0310 (16) 0.0269 (14) 0.0517 (15) −0.0027 (12) 0.0041 (13) 0.0184 (11)C4 0.0358 (16) 0.0388 (15) 0.0278 (11) 0.0018 (14) 0.0042 (12) 0.0111 (10)C5 0.0295 (14) 0.0222 (11) 0.0252 (10) 0.0001 (11) 0.0019 (12) 0.0020 (8)C6 0.0132 (13) 0.0196 (11) 0.0245 (10) 0.0004 (10) 0.0034 (10) 0.0023 (8)C7 0.0159 (12) 0.0190 (11) 0.0160 (8) −0.0046 (10) −0.0001 (9) −0.0016 (8)C8 0.0167 (13) 0.0180 (11) 0.0150 (9) 0.0035 (10) −0.0007 (9) −0.0005 (8)supporting informationsup-6Acta Cryst. (2012). E68, o35–o36    C9 0.0143 (11) 0.0219 (11) 0.0211 (9) −0.0030 (11) 0.0023 (10) 0.0026 (8)C10 0.0110 (11) 0.0163 (11) 0.0184 (9) 0.0043 (9) −0.0003 (8) 0.0024 (8)C11 0.0165 (12) 0.0177 (10) 0.0159 (9) 0.0022 (9) −0.0006 (9) 0.0031 (8)C12 0.0146 (12) 0.0173 (11) 0.0167 (9) 0.0016 (9) −0.0039 (9) −0.0036 (8)C13 0.0105 (12) 0.0149 (10) 0.0204 (9) 0.0012 (9) −0.0012 (9) 0.0026 (7)C14 0.0118 (11) 0.0167 (11) 0.0163 (9) 0.0040 (9) 0.0005 (9) 0.0015 (8)C15 0.0149 (11) 0.0136 (11) 0.0174 (9) 0.0034 (9) −0.0026 (9) −0.0004 (7)C16 0.0171 (13) 0.0353 (14) 0.0383 (12) −0.0027 (12) −0.0068 (12) 0.0025 (10)C17 0.0178 (12) 0.0250 (12) 0.0345 (11) 0.0039 (14) 0.0010 (11) 0.0037 (9)C18 0.0256 (12) 0.0229 (12) 0.0186 (9) −0.0033 (11) 0.0040 (9) −0.0058 (9)Geometric parameters (Å, º) Br1—C12 1.903 (2) C7—H7A 1.0000O1—C8 1.435 (3) C8—C10 1.499 (3)O1—C7 1.458 (3) C8—H8A 1.0000O2—C13 1.347 (3) C9—C16 1.519 (4)O2—H2 0.8499 (10) C9—H9A 1.0000O3—C14 1.367 (2) C10—C11 1.386 (3)O3—C18 1.441 (2) C10—C15 1.409 (3)N1—C17 1.455 (3) C11—C12 1.378 (3)N1—C8 1.456 (3) C11—H11A 0.9500N1—C9 1.474 (3) C12—C13 1.387 (3)C1—C2 1.392 (3) C13—C14 1.413 (3)C1—C6 1.394 (3) C14—C15 1.382 (3)C1—H1A 0.9500 C15—H15A 0.9500C2—C3 1.379 (4) C16—H16A 0.9800C2—H2A 0.9500 C16—H16B 0.9800C3—C4 1.387 (4) C16—H16C 0.9800C3—H3A 0.9500 C17—H17A 0.9800C4—C5 1.389 (3) C17—H17B 0.9800C4—H4A 0.9500 C17—H17C 0.9800C5—C6 1.391 (3) C18—H18A 0.9800C5—H5A 0.9500 C18—H18B 0.9800C6—C7 1.512 (3) C18—H18C 0.9800C7—C9 1.526 (3)C8—O1—C7 107.31 (16) N1—C9—H9A 109.2C13—O2—H2 107.2 (18) C16—C9—H9A 109.2C14—O3—C18 116.80 (16) C7—C9—H9A 109.2C17—N1—C8 113.71 (18) C11—C10—C15 119.30 (19)C17—N1—C9 113.94 (18) C11—C10—C8 119.56 (18)C8—N1—C9 101.95 (17) C15—C10—C8 120.99 (18)C2—C1—C6 120.4 (2) C12—C11—C10 120.15 (19)C2—C1—H1A 119.8 C12—C11—H11A 119.9C6—C1—H1A 119.8 C10—C11—H11A 119.9C3—C2—C1 119.8 (2) C11—C12—C13 122.20 (19)C3—C2—H2A 120.1 C11—C12—Br1 119.62 (15)supporting informationsup-7Acta Cryst. (2012). E68, o35–o36    C1—C2—H2A 120.1 C13—C12—Br1 118.16 (16)C2—C3—C4 120.5 (2) O2—C13—C12 121.22 (18)C2—C3—H3A 119.7 O2—C13—C14 121.44 (18)C4—C3—H3A 119.7 C12—C13—C14 117.32 (19)C3—C4—C5 119.7 (2) O3—C14—C15 126.11 (18)C3—C4—H4A 120.2 O3—C14—C13 112.63 (18)C5—C4—H4A 120.2 C15—C14—C13 121.26 (18)C4—C5—C6 120.5 (2) C14—C15—C10 119.68 (19)C4—C5—H5A 119.7 C14—C15—H15A 120.2C6—C5—H5A 119.7 C10—C15—H15A 120.2C5—C6—C1 119.1 (2) C9—C16—H16A 109.5C5—C6—C7 120.85 (18) C9—C16—H16B 109.5C1—C6—C7 120.07 (18) H16A—C16—H16B 109.5O1—C7—C6 111.27 (17) C9—C16—H16C 109.5O1—C7—C9 104.75 (16) H16A—C16—H16C 109.5C6—C7—C9 115.34 (19) H16B—C16—H16C 109.5O1—C7—H7A 108.4 N1—C17—H17A 109.5C6—C7—H7A 108.4 N1—C17—H17B 109.5C9—C7—H7A 108.4 H17A—C17—H17B 109.5O1—C8—N1 103.74 (17) N1—C17—H17C 109.5O1—C8—C10 112.86 (18) H17A—C17—H17C 109.5N1—C8—C10 112.88 (17) H17B—C17—H17C 109.5O1—C8—H8A 109.1 O3—C18—H18A 109.5N1—C8—H8A 109.1 O3—C18—H18B 109.5C10—C8—H8A 109.1 H18A—C18—H18B 109.5N1—C9—C16 113.81 (18) O3—C18—H18C 109.5N1—C9—C7 101.0 (2) H18A—C18—H18C 109.5C16—C9—C7 113.98 (18) H18B—C18—H18C 109.5C6—C1—C2—C3 −0.5 (5) C6—C7—C9—N1 149.13 (17)C1—C2—C3—C4 0.0 (5) O1—C7—C9—C16 148.90 (18)C2—C3—C4—C5 0.0 (5) C6—C7—C9—C16 −88.4 (2)C3—C4—C5—C6 0.5 (5) O1—C8—C10—C11 −129.0 (2)C4—C5—C6—C1 −1.0 (4) N1—C8—C10—C11 113.7 (2)C4—C5—C6—C7 178.2 (3) O1—C8—C10—C15 55.5 (3)C2—C1—C6—C5 1.0 (4) N1—C8—C10—C15 −61.8 (3)C2—C1—C6—C7 −178.2 (2) C15—C10—C11—C12 1.4 (3)C8—O1—C7—C6 −124.92 (17) C8—C10—C11—C12 −174.2 (2)C8—O1—C7—C9 0.36 (18) C10—C11—C12—C13 0.0 (3)C5—C6—C7—O1 50.7 (3) C10—C11—C12—Br1 −178.39 (17)C1—C6—C7—O1 −130.1 (2) C11—C12—C13—O2 178.6 (2)C5—C6—C7—C9 −68.4 (3) Br1—C12—C13—O2 −3.0 (3)C1—C6—C7—C9 110.7 (2) C11—C12—C13—C14 −2.5 (3)C7—O1—C8—N1 −27.71 (18) Br1—C12—C13—C14 175.97 (16)C7—O1—C8—C10 −150.23 (16) C18—O3—C14—C15 −10.8 (3)C17—N1—C8—O1 167.85 (16) C18—O3—C14—C13 169.59 (19)C9—N1—C8—O1 44.77 (18) O2—C13—C14—O3 2.2 (3)C17—N1—C8—C10 −69.6 (2) C12—C13—C14—O3 −176.71 (19)supporting informationsup-8Acta Cryst. (2012). E68, o35–o36    C9—N1—C8—C10 167.27 (17) O2—C13—C14—C15 −177.4 (2)C17—N1—C9—C16 71.3 (2) C12—C13—C14—C15 3.6 (3)C8—N1—C9—C16 −165.77 (19) O3—C14—C15—C10 178.0 (2)C17—N1—C9—C7 −166.13 (17) C13—C14—C15—C10 −2.3 (3)C8—N1—C9—C7 −43.20 (18) C11—C10—C15—C14 −0.2 (3)O1—C7—C9—N1 26.45 (18) C8—C10—C15—C14 175.3 (2)Hydrogen-bond geometry (Å, º) Cg2 is the centroid of the C1–C6 phenyl ring.D—H···A D—H H···A D···A D—H···AO2—H2···O1i 0.85 (1) 2.03 (1) 2.7853 (19) 148 (2)C15—H15A···O2ii 0.95 2.46 3.232 (3) 138C18—H18A···Cg2i 0.98 2.96 3.679 (3) 131Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2.

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

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

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