4-(3,4-Dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-2-methoxy-phenol.

In the title compound, C(18)H(21)NO(3), the oxazolidine ring adopts an envelope conformation with the N atom at the flap position. The two benzene rings make dihedral angles of 74.27 (14) and 73.26 (15)° with the mean plane through the oxazolidine ring. In the crystal structure, O-H⋯O and C-H⋯O hydrogen bonds connect adjacent mol-ecules into chains along [010] incorporating R(2) (2)(8) loops and further stabilization is provided by weak inter-molecular C-H⋯π inter-actions.

Related literature

For general background to and applications of the title oxazolidine compound, see: Fitzgerald et al. (2005 ▶); Kamat et al. (2000 ▶); Kumar et al. (2004 ▶); Walton et al. (2003 ▶). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For a related structure, see: Duffy et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H21NO3

M = 299.36

Orthorhombic,

a = 7.8893 (6) Å

b = 11.7697 (9) Å

c = 17.4392 (13) Å

V = 1619.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.31 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.975, T max = 0.987

9140 measured reflections

2131 independent reflections

1622 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.096

S = 1.07

2131 reflections

206 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

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 datablocks global, I. DOI: 10.1107/S1600536810018891/hb5455sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018891/hb5455Isup2.hkl

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

C18H21NO3	F(000) = 640
Mr = 299.36	Dx = 1.228 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2249 reflections
a = 7.8893 (6) Å	θ = 2.3–30.0°
b = 11.7697 (9) Å	µ = 0.08 mm−1
c = 17.4392 (13) Å	T = 120 K
V = 1619.3 (2) Å3	Block, colourless
Z = 4	0.31 × 0.15 × 0.15 mm

Bruker SMART APEXII CCD diffractometer	2131 independent reflections
Radiation source: fine-focus sealed tube	1622 reflections with I > 2σ(I)
graphite	Rint = 0.067
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.975, Tmax = 0.987	k = −15→12
9140 measured reflections	l = −22→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0389P)2 + 0.1539P] where P = (Fo2 + 2Fc2)/3
2131 reflections	(Δ/σ)max < 0.001
206 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1)K.

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.

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 > 2sigma(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	0.6439 (2)	−0.37357 (17)	0.20663 (13)	0.0265 (5)
O2	0.5613 (2)	−0.21380 (16)	0.30639 (11)	0.0268 (5)
O3	0.2181 (2)	0.07593 (15)	0.14249 (11)	0.0212 (4)
N1	0.0098 (3)	−0.05656 (19)	0.15472 (13)	0.0233 (5)
C1	0.3559 (4)	−0.2052 (2)	0.08866 (16)	0.0253 (7)
H1A	0.3145	−0.2043	0.0387	0.030*
C2	0.4683 (3)	−0.2903 (2)	0.11104 (17)	0.0255 (6)
H2A	0.4999	−0.3467	0.0765	0.031*
C3	0.5324 (3)	−0.2906 (2)	0.18443 (17)	0.0215 (6)
C4	0.4854 (3)	−0.2053 (2)	0.23596 (16)	0.0206 (6)
C5	0.3704 (3)	−0.1229 (2)	0.21429 (16)	0.0207 (6)
H5A	0.3363	−0.0678	0.2493	0.025*
C6	0.3054 (3)	−0.1223 (2)	0.13965 (16)	0.0210 (6)
C7	0.1731 (3)	−0.0363 (2)	0.11753 (16)	0.0203 (6)
H7A	0.1583	−0.0366	0.0617	0.024*
C8	−0.0791 (3)	0.0517 (2)	0.14323 (17)	0.0234 (6)
H8A	−0.1136	0.0585	0.0894	0.028*
C9	0.0619 (3)	0.1373 (2)	0.16032 (15)	0.0217 (6)
H9A	0.0606	0.1547	0.2153	0.026*
C10	0.0490 (3)	0.2465 (2)	0.11626 (16)	0.0204 (6)
C11	−0.0056 (4)	0.3445 (2)	0.15220 (18)	0.0284 (7)
H11A	−0.0288	0.3435	0.2045	0.034*
C12	−0.0263 (4)	0.4449 (3)	0.1110 (2)	0.0365 (8)
H12A	−0.0623	0.5105	0.1358	0.044*
C13	0.0064 (4)	0.4468 (3)	0.0336 (2)	0.0355 (8)
H13A	−0.0090	0.5134	0.0058	0.043*
C14	0.0625 (4)	0.3493 (3)	−0.00306 (18)	0.0328 (7)
H14A	0.0852	0.3504	−0.0554	0.039*
C15	0.0844 (4)	0.2504 (3)	0.03850 (17)	0.0264 (7)
H15A	0.1236	0.1854	0.0139	0.032*
C16	0.5385 (4)	−0.1212 (2)	0.35869 (16)	0.0275 (6)
H16A	0.6074	−0.1333	0.4033	0.041*
H16B	0.4215	−0.1169	0.3736	0.041*
H16C	0.5713	−0.0516	0.3342	0.041*
C17	−0.0798 (4)	−0.1538 (3)	0.12300 (19)	0.0343 (8)
H17A	−0.0103	−0.2204	0.1276	0.051*
H17C	−0.1044	−0.1402	0.0699	0.051*
H17D	−0.1838	−0.1651	0.1506	0.051*
C18	−0.2325 (3)	0.0658 (3)	0.19449 (18)	0.0320 (7)
H18A	−0.3176	0.0114	0.1803	0.048*
H18D	−0.2771	0.1412	0.1888	0.048*
H18B	−0.2001	0.0538	0.2469	0.048*
H1O1	0.658 (4)	−0.368 (3)	0.259 (2)	0.048 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0250 (10)	0.0216 (11)	0.0331 (12)	0.0061 (8)	−0.0054 (9)	−0.0006 (10)
O2	0.0282 (10)	0.0223 (10)	0.0299 (11)	0.0039 (8)	−0.0080 (9)	−0.0025 (9)
O3	0.0145 (8)	0.0178 (9)	0.0314 (11)	0.0008 (7)	−0.0010 (8)	−0.0004 (9)
N1	0.0171 (10)	0.0220 (12)	0.0309 (13)	−0.0005 (10)	0.0003 (10)	0.0015 (11)
C1	0.0255 (14)	0.0259 (15)	0.0246 (16)	−0.0010 (13)	0.0001 (13)	0.0009 (14)
C2	0.0257 (15)	0.0193 (14)	0.0316 (16)	0.0008 (12)	0.0024 (13)	−0.0037 (13)
C3	0.0163 (13)	0.0167 (13)	0.0316 (16)	−0.0010 (11)	−0.0015 (12)	0.0033 (13)
C4	0.0170 (13)	0.0195 (13)	0.0252 (15)	−0.0042 (11)	−0.0015 (11)	0.0011 (13)
C5	0.0178 (12)	0.0160 (14)	0.0283 (15)	−0.0010 (11)	0.0025 (11)	−0.0022 (13)
C6	0.0188 (13)	0.0188 (14)	0.0255 (15)	−0.0039 (11)	0.0013 (12)	0.0027 (13)
C7	0.0190 (13)	0.0176 (14)	0.0243 (15)	−0.0006 (11)	−0.0014 (11)	0.0003 (12)
C8	0.0180 (12)	0.0246 (15)	0.0274 (15)	−0.0004 (12)	−0.0017 (12)	0.0051 (13)
C9	0.0179 (12)	0.0240 (14)	0.0233 (15)	0.0037 (12)	0.0014 (12)	0.0006 (13)
C10	0.0110 (12)	0.0238 (15)	0.0263 (15)	0.0001 (11)	−0.0047 (11)	−0.0001 (12)
C11	0.0229 (14)	0.0284 (16)	0.0339 (17)	0.0034 (13)	0.0024 (13)	−0.0019 (14)
C12	0.0288 (17)	0.0238 (17)	0.057 (2)	0.0078 (14)	−0.0003 (16)	−0.0010 (16)
C13	0.0293 (15)	0.0245 (17)	0.053 (2)	0.0011 (15)	−0.0081 (16)	0.0161 (16)
C14	0.0293 (16)	0.0375 (19)	0.0315 (17)	−0.0066 (15)	−0.0048 (14)	0.0086 (15)
C15	0.0249 (14)	0.0245 (15)	0.0298 (16)	−0.0007 (13)	−0.0014 (13)	0.0012 (13)
C16	0.0293 (15)	0.0271 (15)	0.0259 (15)	0.0059 (13)	−0.0032 (13)	−0.0018 (14)
C17	0.0235 (14)	0.0289 (17)	0.050 (2)	−0.0086 (13)	0.0014 (15)	0.0005 (16)
C18	0.0220 (14)	0.0352 (17)	0.0389 (18)	0.0019 (13)	0.0051 (14)	0.0042 (16)

O1—C3	1.370 (3)	C9—C10	1.501 (4)
O1—H1O1	0.92 (3)	C9—H9A	0.9800
O2—C4	1.370 (3)	C10—C11	1.382 (4)
O2—C16	1.432 (3)	C10—C15	1.385 (4)
O3—C7	1.435 (3)	C11—C12	1.393 (4)
O3—C9	1.462 (3)	C11—H11A	0.9300
N1—C17	1.455 (4)	C12—C13	1.374 (5)
N1—C7	1.462 (3)	C12—H12A	0.9300
N1—C8	1.468 (3)	C13—C14	1.386 (4)
C1—C6	1.379 (4)	C13—H13A	0.9300
C1—C2	1.394 (4)	C14—C15	1.382 (4)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.376 (4)	C15—H15A	0.9300
C2—H2A	0.9300	C16—H16A	0.9600
C3—C4	1.397 (4)	C16—H16B	0.9600
C4—C5	1.381 (4)	C16—H16C	0.9600
C5—C6	1.399 (4)	C17—H17A	0.9600
C5—H5A	0.9300	C17—H17C	0.9600
C6—C7	1.505 (4)	C17—H17D	0.9600
C7—H7A	0.9800	C18—H18A	0.9600
C8—C18	1.514 (4)	C18—H18D	0.9600
C8—C9	1.530 (4)	C18—H18B	0.9600
C8—H8A	0.9800
C3—O1—H1O1	108 (2)	O3—C9—H9A	108.7
C4—O2—C16	117.4 (2)	C10—C9—H9A	108.7
C7—O3—C9	108.10 (19)	C8—C9—H9A	108.7
C17—N1—C7	112.8 (2)	C11—C10—C15	118.6 (3)
C17—N1—C8	113.5 (2)	C11—C10—C9	120.3 (3)
C7—N1—C8	102.6 (2)	C15—C10—C9	121.0 (2)
C6—C1—C2	120.8 (3)	C10—C11—C12	120.7 (3)
C6—C1—H1A	119.6	C10—C11—H11A	119.7
C2—C1—H1A	119.6	C12—C11—H11A	119.7
C3—C2—C1	119.7 (3)	C13—C12—C11	119.9 (3)
C3—C2—H2A	120.1	C13—C12—H12A	120.0
C1—C2—H2A	120.1	C11—C12—H12A	120.0
O1—C3—C2	120.0 (3)	C12—C13—C14	120.0 (3)
O1—C3—C4	120.0 (2)	C12—C13—H13A	120.0
C2—C3—C4	119.9 (2)	C14—C13—H13A	120.0
O2—C4—C5	125.7 (2)	C15—C14—C13	119.7 (3)
O2—C4—C3	114.1 (2)	C15—C14—H14A	120.1
C5—C4—C3	120.2 (2)	C13—C14—H14A	120.1
C4—C5—C6	119.9 (3)	C14—C15—C10	121.0 (3)
C4—C5—H5A	120.0	C14—C15—H15A	119.5
C6—C5—H5A	120.0	C10—C15—H15A	119.5
C1—C6—C5	119.4 (2)	O2—C16—H16A	109.5
C1—C6—C7	120.8 (3)	O2—C16—H16B	109.5
C5—C6—C7	119.8 (2)	H16A—C16—H16B	109.5
O3—C7—N1	103.5 (2)	O2—C16—H16C	109.5
O3—C7—C6	111.7 (2)	H16A—C16—H16C	109.5
N1—C7—C6	112.8 (2)	H16B—C16—H16C	109.5
O3—C7—H7A	109.5	N1—C17—H17A	109.5
N1—C7—H7A	109.5	N1—C17—H17C	109.5
C6—C7—H7A	109.5	H17A—C17—H17C	109.5
N1—C8—C18	113.4 (2)	N1—C17—H17D	109.5
N1—C8—C9	101.4 (2)	H17A—C17—H17D	109.5
C18—C8—C9	113.2 (2)	H17C—C17—H17D	109.5
N1—C8—H8A	109.5	C8—C18—H18A	109.5
C18—C8—H8A	109.5	C8—C18—H18D	109.5
C9—C8—H8A	109.5	H18A—C18—H18D	109.5
O3—C9—C10	111.8 (2)	C8—C18—H18B	109.5
O3—C9—C8	104.25 (19)	H18A—C18—H18B	109.5
C10—C9—C8	114.5 (2)	H18D—C18—H18B	109.5
C6—C1—C2—C3	−1.3 (4)	C5—C6—C7—N1	−69.3 (3)
C1—C2—C3—O1	−179.5 (2)	C17—N1—C8—C18	73.7 (3)
C1—C2—C3—C4	−0.4 (4)	C7—N1—C8—C18	−164.2 (2)
C16—O2—C4—C5	−9.2 (4)	C17—N1—C8—C9	−164.6 (2)
C16—O2—C4—C3	171.4 (2)	C7—N1—C8—C9	−42.5 (2)
O1—C3—C4—O2	0.7 (3)	C7—O3—C9—C10	−124.5 (2)
C2—C3—C4—O2	−178.4 (2)	C7—O3—C9—C8	−0.3 (3)
O1—C3—C4—C5	−178.7 (2)	N1—C8—C9—O3	26.4 (2)
C2—C3—C4—C5	2.2 (4)	C18—C8—C9—O3	148.2 (2)
O2—C4—C5—C6	178.4 (2)	N1—C8—C9—C10	148.9 (2)
C3—C4—C5—C6	−2.3 (4)	C18—C8—C9—C10	−89.3 (3)
C2—C1—C6—C5	1.2 (4)	O3—C9—C10—C11	−136.8 (2)
C2—C1—C6—C7	−174.8 (2)	C8—C9—C10—C11	104.9 (3)
C4—C5—C6—C1	0.6 (4)	O3—C9—C10—C15	45.9 (3)
C4—C5—C6—C7	176.7 (2)	C8—C9—C10—C15	−72.4 (3)
C9—O3—C7—N1	−26.2 (2)	C15—C10—C11—C12	0.7 (4)
C9—O3—C7—C6	−147.9 (2)	C9—C10—C11—C12	−176.7 (3)
C17—N1—C7—O3	165.9 (2)	C10—C11—C12—C13	0.5 (4)
C8—N1—C7—O3	43.3 (2)	C11—C12—C13—C14	−1.0 (5)
C17—N1—C7—C6	−73.2 (3)	C12—C13—C14—C15	0.3 (5)
C8—N1—C7—C6	164.3 (2)	C13—C14—C15—C10	0.9 (4)
C1—C6—C7—O3	−137.2 (3)	C11—C10—C15—C14	−1.4 (4)
C5—C6—C7—O3	46.8 (3)	C9—C10—C15—C14	176.0 (3)
C1—C6—C7—N1	106.7 (3)

Cg1 is the centroid of the C10–C15 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O3i	0.92 (4)	2.08 (3)	2.909 (3)	148 (3)
C5—H5A···O1ii	0.93	2.42	3.244 (3)	148
C16—H16A···Cg1iii	0.96	2.91	3.628 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O3i	0.92 (4)	2.08 (3)	2.909 (3)	148 (3)
C5—H5A⋯O1ii	0.93	2.42	3.244 (3)	148
C16—H16A⋯Cg1iii	0.96	2.91	3.628 (3)	133

Symmetry codes: (i) ; (ii) ; (iii) .