(6R)-2-tert-Butyl-6-[(4R,5S)-3-isopropyl-4-methyl-5-phenyl-oxazolidin-2-yl]phenol.

In the title compound, C(23)H(31)NO(2), the lone pair on the nitro-gen atom is oriented to facilitate intra-molecular hydrogen bonding with the hydr-oxy group residing on the phenyl substituent. The five-membered ring adopts an envelope confornmation with the O atom at the flap. The absolute stereochemistry was verified by measurement of optical activity using a digital polarimeter.

Related literature

For related structures and background to the use of chiral oxazolidines in asymmetric synthesis, see: Agami & Couty (2004 ▶); Anderson et al. (2010 ▶); Campbell et al. (2010 ▶); Ge et al. (2003 ▶); Hitchcock et al. (2004 ▶); Nakano et al. (2001 ▶); Parrott et al. (2008 ▶); 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

C23H31NO2

M = 353.49

Monoclinic,

a = 9.5077 (6) Å

b = 7.3257 (5) Å

c = 14.983 (1) Å

β = 101.615 (1)°

V = 1022.20 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 140 K

0.53 × 0.41 × 0.39 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.823, T max = 0.972

9840 measured reflections

2537 independent reflections

2445 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.03

wR(F 2) = 0.082

S = 1.03

2537 reflections

239 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2 and 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (McMahon & Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009591/zl2268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009591/zl2268Isup2.hkl

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

Enhanced figure: interactive version of Fig. 2

C23H31NO2	F(000) = 384
Mr = 353.49	Dx = 1.148 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8065 reflections
a = 9.5077 (6) Å	θ = 2.3–31.2°
b = 7.3257 (5) Å	µ = 0.07 mm−1
c = 14.983 (1) Å	T = 140 K
β = 101.615 (1)°	Block, colourless
V = 1022.20 (12) Å3	0.53 × 0.41 × 0.39 mm
Z = 2

Bruker SMART APEX CCD diffractometer	2445 reflections with I > 2σ(I)
ω scans	Rint = 0.019
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 27.5°, θmin = 1.4°
Tmin = 0.823, Tmax = 0.972	h = −12→12
9840 measured reflections	k = −9→9
2537 independent reflections	l = −19→19

Refinement on F2	1 restraint
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.03	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.1569P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.082	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.22 e Å−3
2537 reflections	Δρmin = −0.15 e Å−3
239 parameters

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.09280 (10)	0.05027 (15)	0.41402 (6)	0.0211 (2)
O22	0.31418 (10)	0.10290 (16)	0.25925 (7)	0.0232 (2)
N3	0.18897 (12)	0.30937 (18)	0.36374 (8)	0.0188 (2)
C16	0.06048 (15)	0.07792 (19)	0.25140 (9)	0.0202 (3)
C17	0.18240 (15)	0.0483 (2)	0.21331 (9)	0.0199 (3)
C2	0.06770 (14)	0.1778 (2)	0.34047 (9)	0.0192 (3)
H2	−0.0251	0.2429	0.3394	0.023*
C18	0.16944 (16)	−0.0342 (2)	0.12667 (9)	0.0232 (3)
C7	0.25468 (16)	−0.1201 (2)	0.56806 (11)	0.0261 (3)
H7	0.2477	−0.1741	0.5097	0.031*
C5	0.13056 (14)	0.1627 (2)	0.49354 (9)	0.0205 (3)
H5	0.0424	0.2249	0.5052	0.025*
C12	0.39146 (14)	0.2626 (2)	0.49450 (10)	0.0241 (3)
H12A	0.4486	0.3598	0.4743	0.036*
H12B	0.4116	0.1466	0.467	0.036*
H12C	0.4165	0.2524	0.561	0.036*
C11	0.20485 (16)	0.1286 (3)	0.66191 (10)	0.0287 (3)
H11	0.1633	0.2448	0.6677	0.034*
C19	0.03264 (18)	−0.0911 (2)	0.08297 (10)	0.0277 (3)
H19	0.0214	−0.1482	0.025	0.033*
C8	0.32400 (16)	−0.2135 (3)	0.64589 (11)	0.0336 (4)
H8	0.3641	−0.3308	0.6404	0.04*
C21	−0.07376 (15)	0.0199 (2)	0.20467 (10)	0.0240 (3)
H21	−0.1562	0.0401	0.2301	0.029*
C6	0.19613 (14)	0.0511 (2)	0.57569 (9)	0.0220 (3)
C13	0.15692 (15)	0.4965 (2)	0.32618 (10)	0.0227 (3)
H13	0.0848	0.5542	0.3575	0.027*
C14	0.29374 (16)	0.6112 (2)	0.34524 (11)	0.0264 (3)
H14A	0.3331	0.6128	0.4109	0.04*
H14B	0.2714	0.7363	0.3237	0.04*
H14C	0.3645	0.5583	0.3133	0.04*
C9	0.33429 (17)	−0.1348 (3)	0.73133 (11)	0.0382 (5)
H9	0.3823	−0.1975	0.7842	0.046*
C4	0.23252 (14)	0.3075 (2)	0.46524 (9)	0.0199 (3)
H4	0.2128	0.4296	0.49	0.024*
C23	0.30071 (18)	−0.0529 (3)	0.08149 (10)	0.0293 (4)
C15	0.09567 (18)	0.4936 (2)	0.22390 (10)	0.0293 (3)
H15A	0.0077	0.4202	0.2117	0.044*
H15B	0.1663	0.4401	0.1921	0.044*
H15C	0.0737	0.6185	0.2022	0.044*
C20	−0.08768 (17)	−0.0671 (2)	0.12135 (11)	0.0280 (3)
H20	−0.1789	−0.1101	0.0905	0.034*
C25	0.41693 (19)	−0.1736 (3)	0.13943 (11)	0.0374 (4)
H25A	0.4993	−0.1833	0.1096	0.056*
H25B	0.3776	−0.2955	0.1458	0.056*
H25C	0.4478	−0.1187	0.1999	0.056*
C10	0.27441 (18)	0.0356 (3)	0.73926 (11)	0.0364 (4)
H10	0.2809	0.089	0.7977	0.044*
C24	0.3624 (2)	0.1375 (3)	0.06962 (12)	0.0380 (4)
H24A	0.4461	0.1258	0.0411	0.057*
H24B	0.3913	0.1958	0.1294	0.057*
H24C	0.2891	0.2122	0.0308	0.057*
C26	0.2602 (2)	−0.1396 (4)	−0.01343 (12)	0.0464 (5)
H26A	0.3459	−0.1496	−0.04	0.07*
H26B	0.1886	−0.0632	−0.0526	0.07*
H26C	0.2201	−0.2615	−0.0083	0.07*
H22	0.301 (2)	0.178 (4)	0.3002 (15)	0.039 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0221 (5)	0.0231 (5)	0.0171 (4)	−0.0026 (4)	0.0016 (3)	0.0013 (4)
O22	0.0192 (5)	0.0296 (6)	0.0200 (5)	0.0013 (4)	0.0017 (4)	−0.0037 (5)
N3	0.0171 (5)	0.0183 (6)	0.0196 (5)	0.0004 (5)	0.0007 (4)	0.0005 (5)
C16	0.0218 (6)	0.0182 (7)	0.0189 (6)	0.0006 (5)	0.0005 (5)	0.0016 (5)
C17	0.0210 (6)	0.0186 (6)	0.0186 (6)	0.0013 (5)	0.0002 (5)	0.0027 (5)
C2	0.0163 (6)	0.0207 (7)	0.0199 (6)	0.0001 (5)	0.0016 (5)	0.0018 (5)
C18	0.0280 (7)	0.0218 (7)	0.0186 (6)	0.0020 (6)	0.0023 (5)	0.0028 (6)
C7	0.0202 (6)	0.0354 (9)	0.0238 (7)	0.0010 (6)	0.0074 (5)	0.0044 (6)
C5	0.0168 (6)	0.0259 (7)	0.0186 (6)	0.0004 (6)	0.0032 (5)	−0.0018 (6)
C12	0.0159 (6)	0.0311 (8)	0.0240 (7)	−0.0015 (6)	0.0010 (5)	0.0041 (6)
C11	0.0261 (7)	0.0388 (9)	0.0218 (7)	−0.0080 (7)	0.0062 (5)	−0.0035 (7)
C19	0.0343 (8)	0.0257 (8)	0.0199 (7)	−0.0005 (7)	−0.0020 (6)	−0.0007 (6)
C8	0.0219 (7)	0.0432 (10)	0.0364 (8)	0.0026 (7)	0.0077 (6)	0.0139 (8)
C21	0.0214 (6)	0.0229 (8)	0.0257 (7)	−0.0005 (6)	−0.0001 (5)	0.0025 (6)
C6	0.0158 (5)	0.0306 (8)	0.0200 (6)	−0.0047 (6)	0.0047 (5)	0.0015 (6)
C13	0.0218 (6)	0.0188 (7)	0.0263 (7)	0.0031 (6)	0.0021 (5)	0.0015 (6)
C14	0.0268 (7)	0.0207 (7)	0.0309 (7)	−0.0014 (6)	0.0035 (6)	0.0017 (6)
C9	0.0233 (7)	0.0620 (13)	0.0265 (8)	−0.0078 (8)	−0.0011 (6)	0.0178 (8)
C4	0.0169 (6)	0.0231 (7)	0.0193 (6)	0.0008 (5)	0.0023 (5)	−0.0014 (5)
C23	0.0330 (8)	0.0385 (9)	0.0166 (6)	0.0029 (7)	0.0054 (6)	0.0001 (7)
C15	0.0308 (8)	0.0258 (8)	0.0278 (7)	0.0002 (7)	−0.0028 (6)	0.0071 (6)
C20	0.0257 (7)	0.0264 (8)	0.0270 (7)	−0.0034 (6)	−0.0065 (6)	−0.0002 (6)
C25	0.0400 (9)	0.0463 (11)	0.0280 (8)	0.0159 (9)	0.0122 (7)	0.0030 (8)
C10	0.0323 (8)	0.0563 (12)	0.0194 (7)	−0.0160 (8)	0.0025 (6)	0.0005 (8)
C24	0.0395 (9)	0.0462 (12)	0.0296 (8)	−0.0040 (9)	0.0101 (7)	0.0074 (8)
C26	0.0501 (10)	0.0676 (15)	0.0227 (8)	0.0003 (11)	0.0100 (7)	−0.0118 (9)

O1—C2	1.4277 (17)	C8—H8	0.95
O1—C5	1.4336 (16)	C21—C20	1.384 (2)
O22—C17	1.3626 (16)	C21—H21	0.95
O22—H22	0.85 (3)	C13—C15	1.526 (2)
N3—C2	1.4893 (18)	C13—C14	1.527 (2)
N3—C13	1.4897 (19)	C13—H13	1
N3—C4	1.4936 (16)	C14—H14A	0.98
C16—C21	1.3929 (19)	C14—H14B	0.98
C16—C17	1.4081 (19)	C14—H14C	0.98
C16—C2	1.5115 (19)	C9—C10	1.386 (3)
C17—C18	1.4144 (19)	C9—H9	0.95
C2—H2	1	C4—H4	1
C18—C19	1.397 (2)	C23—C26	1.534 (2)
C18—C23	1.541 (2)	C23—C24	1.537 (3)
C7—C6	1.386 (2)	C23—C25	1.539 (2)
C7—C8	1.398 (2)	C15—H15A	0.98
C7—H7	0.95	C15—H15B	0.98
C5—C6	1.504 (2)	C15—H15C	0.98
C5—C4	1.552 (2)	C20—H20	0.95
C5—H5	1	C25—H25A	0.98
C12—C4	1.5222 (18)	C25—H25B	0.98
C12—H12A	0.98	C25—H25C	0.98
C12—H12B	0.98	C10—H10	0.95
C12—H12C	0.98	C24—H24A	0.98
C11—C10	1.392 (2)	C24—H24B	0.98
C11—C6	1.398 (2)	C24—H24C	0.98
C11—H11	0.95	C26—H26A	0.98
C19—C20	1.391 (2)	C26—H26B	0.98
C19—H19	0.95	C26—H26C	0.98
C8—C9	1.389 (3)
C2—O1—C5	103.91 (11)	C15—C13—H13	108.6
C17—O22—H22	107.4 (14)	C14—C13—H13	108.6
C2—N3—C13	114.66 (10)	C13—C14—H14A	109.5
C2—N3—C4	105.98 (10)	C13—C14—H14B	109.5
C13—N3—C4	112.75 (11)	H14A—C14—H14B	109.5
C21—C16—C17	119.67 (13)	C13—C14—H14C	109.5
C21—C16—C2	117.76 (12)	H14A—C14—H14C	109.5
C17—C16—C2	122.54 (12)	H14B—C14—H14C	109.5
O22—C17—C16	119.88 (12)	C10—C9—C8	119.90 (16)
O22—C17—C18	119.37 (12)	C10—C9—H9	120
C16—C17—C18	120.74 (12)	C8—C9—H9	120
O1—C2—N3	103.98 (10)	N3—C4—C12	110.54 (11)
O1—C2—C16	109.60 (12)	N3—C4—C5	102.94 (11)
N3—C2—C16	114.54 (11)	C12—C4—C5	114.32 (13)
O1—C2—H2	109.5	N3—C4—H4	109.6
N3—C2—H2	109.5	C12—C4—H4	109.6
C16—C2—H2	109.5	C5—C4—H4	109.6
C19—C18—C17	117.29 (13)	C26—C23—C24	107.39 (15)
C19—C18—C23	121.83 (13)	C26—C23—C25	107.64 (16)
C17—C18—C23	120.84 (13)	C24—C23—C25	109.81 (15)
C6—C7—C8	120.26 (16)	C26—C23—C18	111.68 (14)
C6—C7—H7	119.9	C24—C23—C18	109.35 (14)
C8—C7—H7	119.9	C25—C23—C18	110.88 (13)
O1—C5—C6	111.15 (12)	C13—C15—H15A	109.5
O1—C5—C4	103.38 (10)	C13—C15—H15B	109.5
C6—C5—C4	114.59 (11)	H15A—C15—H15B	109.5
O1—C5—H5	109.2	C13—C15—H15C	109.5
C6—C5—H5	109.2	H15A—C15—H15C	109.5
C4—C5—H5	109.2	H15B—C15—H15C	109.5
C4—C12—H12A	109.5	C21—C20—C19	119.59 (14)
C4—C12—H12B	109.5	C21—C20—H20	120.2
H12A—C12—H12B	109.5	C19—C20—H20	120.2
C4—C12—H12C	109.5	C23—C25—H25A	109.5
H12A—C12—H12C	109.5	C23—C25—H25B	109.5
H12B—C12—H12C	109.5	H25A—C25—H25B	109.5
C10—C11—C6	120.03 (18)	C23—C25—H25C	109.5
C10—C11—H11	120	H25A—C25—H25C	109.5
C6—C11—H11	120	H25B—C25—H25C	109.5
C20—C19—C18	122.28 (14)	C9—C10—C11	120.27 (16)
C20—C19—H19	118.9	C9—C10—H10	119.9
C18—C19—H19	118.9	C11—C10—H10	119.9
C9—C8—C7	119.96 (18)	C23—C24—H24A	109.5
C9—C8—H8	120	C23—C24—H24B	109.5
C7—C8—H8	120	H24A—C24—H24B	109.5
C20—C21—C16	120.36 (14)	C23—C24—H24C	109.5
C20—C21—H21	119.8	H24A—C24—H24C	109.5
C16—C21—H21	119.8	H24B—C24—H24C	109.5
C7—C6—C11	119.57 (15)	C23—C26—H26A	109.5
C7—C6—C5	122.10 (13)	C23—C26—H26B	109.5
C11—C6—C5	118.23 (15)	H26A—C26—H26B	109.5
N3—C13—C15	111.98 (12)	C23—C26—H26C	109.5
N3—C13—C14	109.53 (12)	H26A—C26—H26C	109.5
C15—C13—C14	109.52 (12)	H26B—C26—H26C	109.5
N3—C13—H13	108.6
C21—C16—C17—O22	−179.25 (14)	C10—C11—C6—C5	−175.15 (14)
C2—C16—C17—O22	3.2 (2)	O1—C5—C6—C7	19.92 (18)
C21—C16—C17—C18	2.2 (2)	C4—C5—C6—C7	−96.81 (16)
C2—C16—C17—C18	−175.41 (13)	O1—C5—C6—C11	−163.77 (12)
C5—O1—C2—N3	44.04 (12)	C4—C5—C6—C11	79.50 (16)
C5—O1—C2—C16	166.94 (10)	C2—N3—C13—C15	−51.80 (16)
C13—N3—C2—O1	−152.55 (11)	C4—N3—C13—C15	−173.20 (11)
C4—N3—C2—O1	−27.52 (13)	C2—N3—C13—C14	−173.49 (11)
C13—N3—C2—C16	87.86 (14)	C4—N3—C13—C14	65.11 (14)
C4—N3—C2—C16	−147.11 (12)	C7—C8—C9—C10	0.7 (2)
C21—C16—C2—O1	91.78 (15)	C2—N3—C4—C12	124.33 (13)
C17—C16—C2—O1	−90.58 (15)	C13—N3—C4—C12	−109.47 (14)
C21—C16—C2—N3	−151.83 (13)	C2—N3—C4—C5	1.83 (13)
C17—C16—C2—N3	25.82 (18)	C13—N3—C4—C5	128.03 (12)
O22—C17—C18—C19	178.79 (14)	O1—C5—C4—N3	24.25 (13)
C16—C17—C18—C19	−2.6 (2)	C6—C5—C4—N3	145.35 (12)
O22—C17—C18—C23	−3.5 (2)	O1—C5—C4—C12	−95.68 (13)
C16—C17—C18—C23	175.10 (14)	C6—C5—C4—C12	25.43 (17)
C2—O1—C5—C6	−165.84 (10)	C19—C18—C23—C26	−0.2 (2)
C2—O1—C5—C4	−42.44 (12)	C17—C18—C23—C26	−177.83 (16)
C17—C18—C19—C20	0.8 (2)	C19—C18—C23—C24	118.53 (17)
C23—C18—C19—C20	−176.94 (16)	C17—C18—C23—C24	−59.10 (18)
C6—C7—C8—C9	0.1 (2)	C19—C18—C23—C25	−120.25 (17)
C17—C16—C21—C20	0.2 (2)	C17—C18—C23—C25	62.1 (2)
C2—C16—C21—C20	177.93 (14)	C16—C21—C20—C19	−2.1 (2)
C8—C7—C6—C11	−1.0 (2)	C18—C19—C20—C21	1.6 (3)
C8—C7—C6—C5	175.25 (13)	C8—C9—C10—C11	−0.4 (2)
C10—C11—C6—C7	1.3 (2)	C6—C11—C10—C9	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O22—H22···N3	0.85 (3)	1.84 (2)	2.6280 (16)	154 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O22—H22⋯N3	0.85 (3)	1.84 (2)	2.6280 (16)	154 (2)