2-Bromo-4-(3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-6-meth-oxy-phenol.

In the title compound, C(18)H(20)BrNO(3), 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 mol-ecules are connected via O-H⋯O and C-H⋯O hydrogen bonds and C-H⋯π inter-actions 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 = 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

Δρmax = 0.32 e Å−3

Δρmin = −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 ▶).

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

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

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

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

C18H20BrNO3	F(000) = 776
Mr = 378.26	Dx = 1.430 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8965 reflections
a = 7.8056 (4) Å	θ = 2.0–24.9°
b = 11.9034 (6) Å	µ = 2.35 mm−1
c = 18.9109 (9) Å	T = 100 K
V = 1757.07 (15) Å3	Block, colourless
Z = 4	0.50 × 0.36 × 0.23 mm

Bruker SMART APEXII CCD area-detector diffractometer	3074 independent reflections
Radiation source: fine-focus sealed tube	2935 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: 83.66 pixels mm-1	θmax = 24.9°, θmin = 2.0°
φ and ω scan	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.383, Tmax = 0.618	l = −22→22
10569 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.056	w = 1/[σ2(Fo2) + (0.0197P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
3074 reflections	Δρmax = 0.32 e Å−3
215 parameters	Δρmin = −0.26 e Å−3
1 restraint	Absolute structure: Flack (1983), 1283 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.004 (7)

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.

	x	y	z	Uiso*/Ueq
Br1	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)
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)*

	U11	U22	U33	U12	U13	U23
Br1	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)
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)

Br1—C12	1.903 (2)	C7—H7A	1.0000
O1—C8	1.435 (3)	C8—C10	1.499 (3)
O1—C7	1.458 (3)	C8—H8A	1.0000
O2—C13	1.347 (3)	C9—C16	1.519 (4)
O2—H2	0.8499 (10)	C9—H9A	1.0000
O3—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	0.9500
N1—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	0.9500
C2—C3	1.379 (4)	C16—H16A	0.9800
C2—H2A	0.9500	C16—H16B	0.9800
C3—C4	1.387 (4)	C16—H16C	0.9800
C3—H3A	0.9500	C17—H17A	0.9800
C4—C5	1.389 (3)	C17—H17B	0.9800
C4—H4A	0.9500	C17—H17C	0.9800
C5—C6	1.391 (3)	C18—H18A	0.9800
C5—H5A	0.9500	C18—H18B	0.9800
C6—C7	1.512 (3)	C18—H18C	0.9800
C7—C9	1.526 (3)
C8—O1—C7	107.31 (16)	N1—C9—H9A	109.2
C13—O2—H2	107.2 (18)	C16—C9—H9A	109.2
C14—O3—C18	116.80 (16)	C7—C9—H9A	109.2
C17—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	119.9
C6—C1—H1A	119.8	C10—C11—H11A	119.9
C3—C2—C1	119.8 (2)	C11—C12—C13	122.20 (19)
C3—C2—H2A	120.1	C11—C12—Br1	119.62 (15)
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	120.2
C6—C5—H5A	119.7	C10—C15—H15A	120.2
C5—C6—C1	119.1 (2)	C9—C16—H16A	109.5
C5—C6—C7	120.85 (18)	C9—C16—H16B	109.5
C1—C6—C7	120.07 (18)	H16A—C16—H16B	109.5
O1—C7—C6	111.27 (17)	C9—C16—H16C	109.5
O1—C7—C9	104.75 (16)	H16A—C16—H16C	109.5
C6—C7—C9	115.34 (19)	H16B—C16—H16C	109.5
O1—C7—H7A	108.4	N1—C17—H17A	109.5
C6—C7—H7A	108.4	N1—C17—H17B	109.5
C9—C7—H7A	108.4	H17A—C17—H17B	109.5
O1—C8—N1	103.74 (17)	N1—C17—H17C	109.5
O1—C8—C10	112.86 (18)	H17A—C17—H17C	109.5
N1—C8—C10	112.88 (17)	H17B—C17—H17C	109.5
O1—C8—H8A	109.1	O3—C18—H18A	109.5
N1—C8—H8A	109.1	O3—C18—H18B	109.5
C10—C8—H8A	109.1	H18A—C18—H18B	109.5
N1—C9—C16	113.81 (18)	O3—C18—H18C	109.5
N1—C9—C7	101.0 (2)	H18A—C18—H18C	109.5
C16—C9—C7	113.98 (18)	H18B—C18—H18C	109.5
C6—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)
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)

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

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) ; (ii) .