(6S)-2-tert-Butyl-6-[(4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol.

The title compound, C(21)H(27)NO(2), exhibits hydrogen bonding between the phenolic H atom and the heterocyclic N atom. The absolute configuration of the mol-ecule is known from the synthetic procedure.

Related literature

For related structures and background to the use of chiral oxazolidines as templates in asymmetric synthesis, see: Agami & Couty (2004 ▶); Campbell et al. (2010 ▶); Koyanagi et al. (2010 ▶); Parrott & Hitchcock (2007 ▶); Parrott et al. (2008 ▶). The synthesis of the title compound is described by Parrott & Hitchcock (2007 ▶). The absolute configuration assignment is based on both optical activity measurements and on the known stereochemistry of the commercially obtained optically pure ephedrine from which it was prepared (Parrott & Hitchcock, 2007 ▶). For geometry checks using Mogul, see: Bruno et al. (2004 ▶). For ring puckering analysis, see: Boeyens (1978 ▶); Cremer & Pople (1975 ▶); Spek (2009 ▶). For a description of the Jmol toolkit for the preparation of enhanced figures, see: McMahon & Hanson (2008 ▶).

Experimental

Crystal data

C21H27NO2

M = 325.44

Monoclinic,

a = 8.3288 (8) Å

b = 9.8657 (9) Å

c = 11.4325 (11) Å

β = 91.667 (1)°

V = 939.00 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 140 K

0.55 × 0.27 × 0.27 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2008 ▶) T min = 0.687, T max = 0.746

9040 measured reflections

2284 independent reflections

2191 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.074

S = 1.04

2284 reflections

221 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), publCIF (McMahon & Westrip, 2008 ▶) and Mercury (Macrae et al., 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009190/zl2269sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009190/zl2269Isup2.hkl

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

Enhanced figure: interactive version of Fig. 2

C21H27NO2	F(000) = 352
Mr = 325.44	Dx = 1.151 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5731 reflections
a = 8.3288 (8) Å	θ = 2.5–3.4°
b = 9.8657 (9) Å	µ = 0.07 mm−1
c = 11.4325 (11) Å	T = 140 K
β = 91.667 (1)°	Rod, colourless
V = 939.00 (15) Å3	0.55 × 0.27 × 0.27 mm
Z = 2

Bruker SMART APEX CCD diffractometer	2191 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (APEX2; Bruker, 2008)	h = −10→10
Tmin = 0.687, Tmax = 0.746	k = −12→12
9040 measured reflections	l = −14→14
2284 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0485P)2 + 0.090P] where P = (Fo2 + 2Fc2)/3
2284 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.14 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.99692 (12)	0.27815 (11)	0.41600 (9)	0.0248 (2)
O20	0.65433 (12)	0.17836 (11)	0.28853 (9)	0.0213 (2)
N3	0.79655 (14)	0.40974 (12)	0.33736 (10)	0.0202 (2)
C16	0.75996 (15)	0.03243 (13)	0.14241 (11)	0.0174 (3)
C14	0.91785 (16)	0.22492 (14)	0.21866 (11)	0.0185 (3)
C19	1.04036 (16)	0.19395 (15)	0.14295 (12)	0.0204 (3)
H19	1.1354	0.2472	0.1438	0.025*
C2	0.94417 (16)	0.33629 (15)	0.30751 (12)	0.0210 (3)
H2	1.0265	0.4016	0.2795	0.025*
C6	0.87041 (16)	0.27789 (16)	0.60254 (12)	0.0233 (3)
C15	0.77689 (15)	0.14637 (14)	0.21694 (11)	0.0177 (3)
C4	0.84147 (17)	0.47509 (15)	0.45020 (13)	0.0241 (3)
H4	0.9104	0.5556	0.4342	0.029*
C21	0.61341 (16)	−0.06087 (14)	0.14940 (12)	0.0189 (3)
C23	0.60832 (17)	−0.12120 (14)	0.27378 (12)	0.0221 (3)
H23A	0.515	−0.1811	0.2791	0.033*
H23B	0.6	−0.0477	0.3309	0.033*
H23C	0.7067	−0.1731	0.2903	0.033*
C8	0.71138 (18)	0.08617 (17)	0.66066 (14)	0.0280 (3)
H8	0.6469	0.0099	0.6402	0.034*
C22	0.62164 (19)	−0.17981 (16)	0.06338 (13)	0.0273 (3)
H22A	0.526	−0.2368	0.0706	0.041*
H22B	0.718	−0.2338	0.0813	0.041*
H22C	0.6261	−0.1448	−0.0167	0.041*
C17	0.88590 (16)	0.00653 (14)	0.06749 (11)	0.0199 (3)
H17	0.8768	−0.0681	0.0152	0.024*
C13	0.7473 (2)	0.50590 (16)	0.24528 (14)	0.0285 (3)
H13A	0.6492	0.5527	0.2679	0.043*
H13B	0.7267	0.4568	0.1718	0.043*
H13C	0.833	0.5724	0.2345	0.043*
C9	0.74020 (19)	0.11793 (18)	0.77790 (14)	0.0316 (4)
H9	0.6968	0.0629	0.8374	0.038*
C5	0.94712 (16)	0.36461 (16)	0.51019 (12)	0.0242 (3)
H5	1.0446	0.4091	0.546	0.029*
C18	1.02423 (16)	0.08575 (15)	0.06636 (12)	0.0215 (3)
H18	1.1069	0.0657	0.0135	0.026*
C11	0.89769 (18)	0.30989 (18)	0.72035 (13)	0.0284 (3)
H11	0.9612	0.3866	0.7412	0.034*
C24	0.45695 (17)	0.01669 (16)	0.11992 (14)	0.0257 (3)
H24A	0.3653	−0.0452	0.1249	0.039*
H24B	0.4612	0.0534	0.0404	0.039*
H24C	0.4447	0.0912	0.1757	0.039*
C10	0.8326 (2)	0.23041 (19)	0.80740 (14)	0.0323 (4)
H10	0.8516	0.2532	0.8874	0.039*
C12	0.69710 (19)	0.52203 (17)	0.51714 (14)	0.0301 (3)
H12A	0.6389	0.5915	0.4717	0.045*
H12B	0.7333	0.5601	0.5926	0.045*
H12C	0.6259	0.4448	0.5304	0.045*
C7	0.77616 (17)	0.16510 (16)	0.57324 (13)	0.0244 (3)
H7	0.7564	0.1424	0.4934	0.029*
H20	0.680 (2)	0.258 (3)	0.3212 (18)	0.040 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0234 (5)	0.0272 (5)	0.0237 (5)	0.0053 (4)	−0.0006 (4)	−0.0053 (4)
O20	0.0187 (4)	0.0178 (5)	0.0278 (5)	−0.0037 (4)	0.0079 (4)	−0.0053 (4)
N3	0.0219 (5)	0.0147 (5)	0.0239 (6)	−0.0007 (4)	0.0028 (4)	−0.0002 (4)
C16	0.0189 (6)	0.0150 (6)	0.0183 (6)	0.0009 (5)	−0.0004 (5)	0.0027 (5)
C14	0.0196 (6)	0.0160 (6)	0.0201 (6)	−0.0004 (5)	0.0022 (5)	0.0015 (5)
C19	0.0175 (6)	0.0212 (7)	0.0227 (6)	−0.0013 (5)	0.0028 (5)	0.0050 (5)
C2	0.0182 (6)	0.0191 (6)	0.0259 (7)	−0.0040 (5)	0.0032 (5)	−0.0010 (5)
C6	0.0200 (6)	0.0257 (7)	0.0242 (7)	0.0065 (6)	−0.0015 (5)	−0.0031 (6)
C15	0.0181 (6)	0.0156 (6)	0.0195 (6)	0.0014 (5)	0.0031 (5)	0.0016 (5)
C4	0.0251 (7)	0.0172 (6)	0.0303 (7)	−0.0042 (5)	0.0023 (5)	−0.0051 (5)
C21	0.0204 (6)	0.0154 (6)	0.0210 (6)	−0.0019 (5)	0.0015 (5)	0.0003 (5)
C23	0.0251 (7)	0.0179 (7)	0.0236 (7)	−0.0022 (5)	0.0037 (5)	0.0032 (5)
C8	0.0248 (7)	0.0253 (7)	0.0338 (8)	0.0065 (6)	−0.0008 (6)	0.0030 (6)
C22	0.0336 (8)	0.0199 (7)	0.0286 (7)	−0.0052 (6)	0.0033 (6)	−0.0057 (6)
C17	0.0253 (6)	0.0176 (6)	0.0168 (6)	0.0032 (5)	0.0003 (5)	0.0014 (5)
C13	0.0336 (8)	0.0194 (7)	0.0328 (8)	0.0022 (6)	0.0040 (6)	0.0046 (6)
C9	0.0305 (8)	0.0345 (9)	0.0298 (7)	0.0155 (7)	0.0038 (6)	0.0080 (7)
C5	0.0196 (6)	0.0255 (7)	0.0275 (7)	−0.0007 (6)	−0.0011 (5)	−0.0086 (6)
C18	0.0205 (6)	0.0256 (7)	0.0186 (6)	0.0047 (6)	0.0058 (5)	0.0033 (5)
C11	0.0265 (7)	0.0315 (8)	0.0267 (7)	0.0098 (6)	−0.0050 (5)	−0.0075 (6)
C24	0.0216 (7)	0.0204 (7)	0.0349 (8)	−0.0012 (6)	−0.0027 (5)	0.0016 (6)
C10	0.0349 (8)	0.0378 (9)	0.0238 (7)	0.0176 (7)	−0.0036 (6)	−0.0032 (7)
C12	0.0319 (8)	0.0247 (7)	0.0339 (8)	0.0047 (6)	0.0043 (6)	−0.0062 (7)
C7	0.0230 (7)	0.0253 (7)	0.0248 (7)	0.0042 (6)	−0.0016 (5)	−0.0021 (6)

O1—C2	1.4243 (17)	C23—H23C	0.98
O1—C5	1.4441 (17)	C8—C7	1.388 (2)
O20—C15	1.3638 (15)	C8—C9	1.391 (2)
O20—H20	0.90 (2)	C8—H8	0.95
N3—C13	1.4667 (19)	C22—H22A	0.98
N3—C2	1.4756 (18)	C22—H22B	0.98
N3—C4	1.4805 (18)	C22—H22C	0.98
C16—C17	1.3970 (18)	C17—C18	1.393 (2)
C16—C15	1.4151 (18)	C17—H17	0.95
C16—C21	1.5327 (18)	C13—H13A	0.98
C14—C19	1.3911 (18)	C13—H13B	0.98
C14—C15	1.4064 (18)	C13—H13C	0.98
C14—C2	1.5081 (19)	C9—C10	1.387 (3)
C19—C18	1.385 (2)	C9—H9	0.95
C19—H19	0.95	C5—H5	1
C2—H2	1	C18—H18	0.95
C6—C11	1.396 (2)	C11—C10	1.389 (2)
C6—C7	1.397 (2)	C11—H11	0.95
C6—C5	1.515 (2)	C24—H24A	0.98
C4—C12	1.516 (2)	C24—H24B	0.98
C4—C5	1.548 (2)	C24—H24C	0.98
C4—H4	1	C10—H10	0.95
C21—C22	1.5338 (19)	C12—H12A	0.98
C21—C24	1.540 (2)	C12—H12B	0.98
C21—C23	1.5433 (18)	C12—H12C	0.98
C23—H23A	0.98	C7—H7	0.95
C23—H23B	0.98
C2—O1—C5	108.87 (11)	C21—C22—H22B	109.5
C15—O20—H20	106.2 (13)	H22A—C22—H22B	109.5
C13—N3—C2	111.67 (11)	C21—C22—H22C	109.5
C13—N3—C4	113.71 (12)	H22A—C22—H22C	109.5
C2—N3—C4	102.96 (11)	H22B—C22—H22C	109.5
C17—C16—C15	116.81 (12)	C18—C17—C16	122.63 (13)
C17—C16—C21	122.37 (12)	C18—C17—H17	118.7
C15—C16—C21	120.75 (11)	C16—C17—H17	118.7
C19—C14—C15	119.83 (12)	N3—C13—H13A	109.5
C19—C14—C2	118.96 (12)	N3—C13—H13B	109.5
C15—C14—C2	121.05 (11)	H13A—C13—H13B	109.5
C18—C19—C14	120.22 (13)	N3—C13—H13C	109.5
C18—C19—H19	119.9	H13A—C13—H13C	109.5
C14—C19—H19	119.9	H13B—C13—H13C	109.5
O1—C2—N3	103.56 (10)	C10—C9—C8	119.59 (15)
O1—C2—C14	109.16 (12)	C10—C9—H9	120.2
N3—C2—C14	114.06 (11)	C8—C9—H9	120.2
O1—C2—H2	110	O1—C5—C6	108.80 (12)
N3—C2—H2	110	O1—C5—C4	104.91 (11)
C14—C2—H2	110	C6—C5—C4	117.42 (11)
C11—C6—C7	119.09 (14)	O1—C5—H5	108.5
C11—C6—C5	119.00 (14)	C6—C5—H5	108.5
C7—C6—C5	121.90 (13)	C4—C5—H5	108.5
O20—C15—C14	120.21 (12)	C19—C18—C17	119.46 (12)
O20—C15—C16	118.81 (12)	C19—C18—H18	120.3
C14—C15—C16	120.97 (11)	C17—C18—H18	120.3
N3—C4—C12	112.88 (12)	C10—C11—C6	120.52 (15)
N3—C4—C5	101.85 (11)	C10—C11—H11	119.7
C12—C4—C5	116.12 (13)	C6—C11—H11	119.7
N3—C4—H4	108.5	C21—C24—H24A	109.5
C12—C4—H4	108.5	C21—C24—H24B	109.5
C5—C4—H4	108.5	H24A—C24—H24B	109.5
C16—C21—C22	112.05 (11)	C21—C24—H24C	109.5
C16—C21—C24	111.12 (11)	H24A—C24—H24C	109.5
C22—C21—C24	107.05 (12)	H24B—C24—H24C	109.5
C16—C21—C23	108.84 (11)	C9—C10—C11	120.18 (15)
C22—C21—C23	107.38 (12)	C9—C10—H10	119.9
C24—C21—C23	110.34 (11)	C11—C10—H10	119.9
C21—C23—H23A	109.5	C4—C12—H12A	109.5
C21—C23—H23B	109.5	C4—C12—H12B	109.5
H23A—C23—H23B	109.5	H12A—C12—H12B	109.5
C21—C23—H23C	109.5	C4—C12—H12C	109.5
H23A—C23—H23C	109.5	H12A—C12—H12C	109.5
H23B—C23—H23C	109.5	H12B—C12—H12C	109.5
C7—C8—C9	120.51 (16)	C8—C7—C6	120.11 (14)
C7—C8—H8	119.7	C8—C7—H7	119.9
C9—C8—H8	119.7	C6—C7—H7	119.9
C21—C22—H22A	109.5
C15—C14—C19—C18	−0.3 (2)	C17—C16—C21—C24	−121.31 (14)
C2—C14—C19—C18	175.24 (12)	C15—C16—C21—C24	61.85 (16)
C5—O1—C2—N3	−29.88 (13)	C17—C16—C21—C23	116.99 (14)
C5—O1—C2—C14	−151.74 (11)	C15—C16—C21—C23	−59.85 (16)
C13—N3—C2—O1	164.76 (12)	C15—C16—C17—C18	1.39 (19)
C4—N3—C2—O1	42.40 (13)	C21—C16—C17—C18	−175.57 (12)
C13—N3—C2—C14	−76.72 (15)	C7—C8—C9—C10	0.9 (2)
C4—N3—C2—C14	160.91 (11)	C2—O1—C5—C6	132.44 (12)
C19—C14—C2—O1	−95.64 (14)	C2—O1—C5—C4	6.00 (14)
C15—C14—C2—O1	79.84 (15)	C11—C6—C5—O1	142.27 (13)
C19—C14—C2—N3	149.09 (13)	C7—C6—C5—O1	−36.26 (17)
C15—C14—C2—N3	−35.44 (17)	C11—C6—C5—C4	−98.86 (15)
C19—C14—C15—O20	−178.14 (12)	C7—C6—C5—C4	82.61 (17)
C2—C14—C15—O20	6.42 (19)	N3—C4—C5—O1	19.92 (13)
C19—C14—C15—C16	2.55 (19)	C12—C4—C5—O1	142.96 (13)
C2—C14—C15—C16	−172.88 (13)	N3—C4—C5—C6	−101.00 (13)
C17—C16—C15—O20	177.65 (12)	C12—C4—C5—C6	22.04 (18)
C21—C16—C15—O20	−5.34 (18)	C14—C19—C18—C17	−1.3 (2)
C17—C16—C15—C14	−3.03 (18)	C16—C17—C18—C19	0.8 (2)
C21—C16—C15—C14	173.98 (12)	C7—C6—C11—C10	0.3 (2)
C13—N3—C4—C12	76.22 (16)	C5—C6—C11—C10	−178.31 (13)
C2—N3—C4—C12	−162.80 (12)	C8—C9—C10—C11	−0.8 (2)
C13—N3—C4—C5	−158.56 (12)	C6—C11—C10—C9	0.2 (2)
C2—N3—C4—C5	−37.58 (13)	C9—C8—C7—C6	−0.4 (2)
C17—C16—C21—C22	−1.61 (18)	C11—C6—C7—C8	−0.2 (2)
C15—C16—C21—C22	−178.45 (12)	C5—C6—C7—C8	178.33 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O20—H20···N3	0.90 (2)	1.79 (2)	2.6244 (16)	154.4 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O20—H20⋯N3	0.90 (2)	1.79 (2)	2.6244 (16)	154.4 (19)