Methyl 5-hy-droxy-3-phenyl-1,2-oxazolidine-5-carboxyl-ate.

In the title compound, C(11)H(13)NO(4), the isoxazolidine ring has an envelope conformation with the O atom as the flap. In the crystal, mol-ecules are liked via N-H⋯O and bifurcated O-H⋯(O,N) hydrogen bonds forming chains propagating along [010]. There are also C-H⋯O inter-actions present.

Related literature

For the use of isoxazolidine-containing compounds as building blocks in synthesis, see: Carrillo et al. (2006 ▶); Lv et al. (2010 ▶); Ibrahem et al. (2007 ▶); Sharma et al. (1999 ▶). For information on conjugation additions to α,β-unsaturated ketones, see: Wu et al. (2006 ▶). For standard bond-lengths see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H13NO4

M = 223.22

Monoclinic,

a = 11.8322 (3) Å

b = 6.0853 (1) Å

c = 15.8570 (3) Å

β = 101.864 (2)°

V = 1117.35 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.85 mm−1

T = 291 K

0.40 × 0.36 × 0.30 mm

Data collection

Oxford Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.726, T max = 0.784

10901 measured reflections

2165 independent reflections

1921 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.097

S = 1.05

2165 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.12 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017576/su2406sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017576/su2406Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017576/su2406Isup3.cml

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

C11H13NO4	F(000) = 472
Mr = 223.22	Dx = 1.327 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 7888 reflections
a = 11.8322 (3) Å	θ = 3.8–71.9°
b = 6.0853 (1) Å	µ = 0.85 mm−1
c = 15.8570 (3) Å	T = 291 K
β = 101.864 (2)°	Block, colourless
V = 1117.35 (4) Å3	0.40 × 0.36 × 0.30 mm
Z = 4

Oxford Gemini S Ultra diffractometer	2165 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1921 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 15.9149 pixels mm-1	θmax = 72.1°, θmin = 5.7°
ω scans	h = −14→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −6→7
Tmin = 0.726, Tmax = 0.784	l = −19→18
10901 measured 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0323P)2 + 0.2933P] where P = (Fo2 + 2Fc2)/3
2165 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.12 e Å−3

Experimental. Absorption correction: (CrysAlisPro; Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.79693 (8)	0.06822 (15)	0.78232 (6)	0.0518 (3)
O2	0.82481 (9)	−0.20986 (16)	0.88556 (6)	0.0604 (4)
O3	1.04065 (10)	−0.0305 (2)	0.89858 (10)	0.0901 (5)
O4	0.96722 (8)	0.30583 (16)	0.89779 (7)	0.0641 (4)
N1	0.67179 (10)	0.0582 (2)	0.76513 (8)	0.0535 (4)
C1	0.3265 (2)	−0.1664 (6)	0.87113 (15)	0.1076 (12)
C2	0.4303 (2)	−0.2651 (4)	0.90278 (16)	0.1061 (10)
C3	0.53265 (17)	−0.1617 (3)	0.89530 (14)	0.0857 (7)
C4	0.53083 (13)	0.0405 (3)	0.85666 (10)	0.0629 (5)
C5	0.42474 (15)	0.1361 (4)	0.82446 (13)	0.0843 (7)
C6	0.32309 (17)	0.0312 (5)	0.83205 (16)	0.1066 (10)
C7	0.63963 (12)	0.1531 (2)	0.84333 (10)	0.0577 (5)
C8	0.74876 (13)	0.1335 (3)	0.91548 (10)	0.0613 (5)
C9	0.83371 (12)	0.0138 (2)	0.87205 (9)	0.0522 (4)
C10	0.96003 (12)	0.0898 (2)	0.89183 (9)	0.0553 (5)
C11	1.08082 (14)	0.4029 (3)	0.90958 (12)	0.0719 (6)
H1	0.25820	−0.23540	0.87650	0.1290*
H2	0.43250	−0.40170	0.92940	0.1270*
H3	0.60300	−0.23020	0.91670	0.1030*
H4	0.6564 (13)	−0.088 (3)	0.7630 (10)	0.062 (4)*
H5	0.42140	0.27220	0.79740	0.1010*
H6	0.25230	0.09750	0.81010	0.1280*
H7	0.62260	0.30950	0.83270	0.0690*
H8A	0.77780	0.27740	0.93560	0.0740*
H8B	0.73310	0.04990	0.96390	0.0740*
H9	0.84150	−0.27740	0.84510	0.0900*
H11A	1.07520	0.55870	0.91730	0.1080*
H11B	1.11280	0.37440	0.85970	0.1080*
H11C	1.12990	0.34020	0.95950	0.1080*

	U11	U22	U33	U12	U13	U23
O1	0.0502 (5)	0.0495 (6)	0.0538 (5)	−0.0012 (4)	0.0064 (4)	0.0012 (4)
O2	0.0731 (7)	0.0478 (6)	0.0577 (6)	−0.0060 (5)	0.0076 (5)	0.0027 (4)
O3	0.0607 (7)	0.0555 (7)	0.1493 (12)	0.0081 (6)	0.0105 (7)	−0.0051 (7)
O4	0.0539 (6)	0.0465 (6)	0.0867 (8)	−0.0031 (4)	0.0023 (5)	0.0018 (5)
N1	0.0496 (6)	0.0472 (7)	0.0608 (7)	−0.0018 (5)	0.0049 (5)	−0.0032 (5)
C1	0.0765 (14)	0.163 (3)	0.0888 (15)	−0.0423 (16)	0.0295 (11)	−0.0271 (16)
C2	0.1073 (18)	0.1077 (18)	0.1067 (16)	−0.0414 (14)	0.0303 (13)	0.0013 (13)
C3	0.0734 (11)	0.0809 (13)	0.1028 (14)	−0.0142 (10)	0.0179 (10)	0.0070 (11)
C4	0.0565 (8)	0.0657 (10)	0.0669 (9)	−0.0030 (7)	0.0136 (7)	−0.0112 (8)
C5	0.0627 (10)	0.0975 (14)	0.0922 (13)	0.0080 (10)	0.0149 (9)	−0.0081 (11)
C6	0.0572 (11)	0.153 (2)	0.1111 (18)	−0.0031 (13)	0.0211 (11)	−0.0198 (17)
C7	0.0593 (8)	0.0481 (8)	0.0653 (9)	0.0006 (6)	0.0120 (7)	−0.0059 (6)
C8	0.0593 (8)	0.0635 (9)	0.0605 (8)	−0.0063 (7)	0.0110 (7)	−0.0115 (7)
C9	0.0564 (8)	0.0463 (7)	0.0511 (7)	−0.0023 (6)	0.0046 (6)	−0.0007 (6)
C10	0.0566 (8)	0.0474 (8)	0.0588 (8)	0.0015 (6)	0.0044 (6)	0.0008 (6)
C11	0.0593 (9)	0.0615 (10)	0.0893 (12)	−0.0118 (8)	0.0026 (8)	0.0030 (8)

O1—N1	1.4507 (16)	C5—C6	1.389 (3)
O1—C9	1.4384 (17)	C7—C8	1.544 (2)
O2—C9	1.3852 (16)	C8—C9	1.517 (2)
O3—C10	1.1897 (18)	C9—C10	1.534 (2)
O4—C10	1.3195 (16)	C1—H1	0.9300
O4—C11	1.445 (2)	C2—H2	0.9300
O2—H9	0.8200	C3—H3	0.9300
N1—C7	1.4866 (19)	C5—H5	0.9300
N1—H4	0.907 (18)	C6—H6	0.9300
C1—C2	1.367 (4)	C7—H7	0.9800
C1—C6	1.350 (5)	C8—H8A	0.9700
C2—C3	1.391 (3)	C8—H8B	0.9700
C3—C4	1.373 (3)	C11—H11A	0.9600
C4—C7	1.511 (2)	C11—H11B	0.9600
C4—C5	1.383 (3)	C11—H11C	0.9600
N1—O1—C9	105.41 (10)	O4—C10—C9	111.15 (11)
C10—O4—C11	117.46 (12)	C2—C1—H1	120.00
C9—O2—H9	109.00	C6—C1—H1	120.00
O1—N1—C7	104.68 (10)	C1—C2—H2	120.00
C7—N1—H4	109.2 (10)	C3—C2—H2	120.00
O1—N1—H4	103.7 (10)	C2—C3—H3	120.00
C2—C1—C6	120.0 (2)	C4—C3—H3	120.00
C1—C2—C3	120.2 (2)	C4—C5—H5	120.00
C2—C3—C4	120.62 (19)	C6—C5—H5	120.00
C3—C4—C5	118.15 (17)	C1—C6—H6	120.00
C3—C4—C7	122.23 (15)	C5—C6—H6	120.00
C5—C4—C7	119.50 (16)	N1—C7—H7	108.00
C4—C5—C6	120.8 (2)	C4—C7—H7	108.00
C1—C6—C5	120.3 (2)	C8—C7—H7	108.00
C4—C7—C8	117.92 (13)	C7—C8—H8A	111.00
N1—C7—C8	105.64 (11)	C7—C8—H8B	111.00
N1—C7—C4	108.18 (12)	C9—C8—H8A	111.00
C7—C8—C9	103.42 (12)	C9—C8—H8B	111.00
O1—C9—O2	111.23 (10)	H8A—C8—H8B	109.00
O1—C9—C8	104.16 (11)	O4—C11—H11A	109.00
C8—C9—C10	118.11 (12)	O4—C11—H11B	109.00
O1—C9—C10	102.52 (11)	O4—C11—H11C	109.00
O2—C9—C8	108.85 (12)	H11A—C11—H11B	109.00
O2—C9—C10	111.50 (11)	H11A—C11—H11C	109.00
O3—C10—O4	124.61 (14)	H11B—C11—H11C	109.00
O3—C10—C9	124.22 (12)
C9—O1—N1—C7	38.90 (12)	C3—C4—C7—C8	−38.7 (2)
N1—O1—C9—O2	76.12 (13)	C5—C4—C7—N1	−94.88 (18)
N1—O1—C9—C8	−40.98 (12)	C5—C4—C7—C8	145.43 (16)
N1—O1—C9—C10	−164.61 (9)	C4—C5—C6—C1	0.0 (4)
C11—O4—C10—O3	2.8 (2)	N1—C7—C8—C9	−3.24 (15)
C11—O4—C10—C9	−175.29 (12)	C4—C7—C8—C9	117.76 (14)
O1—N1—C7—C4	−148.04 (11)	C7—C8—C9—O1	26.43 (14)
O1—N1—C7—C8	−20.90 (13)	C7—C8—C9—O2	−92.30 (13)
C6—C1—C2—C3	0.4 (4)	C7—C8—C9—C10	139.28 (12)
C2—C1—C6—C5	−0.6 (4)	O1—C9—C10—O3	−103.08 (16)
C1—C2—C3—C4	0.4 (3)	O1—C9—C10—O4	75.06 (13)
C2—C3—C4—C5	−1.0 (3)	O2—C9—C10—O3	16.0 (2)
C2—C3—C4—C7	−176.90 (18)	O2—C9—C10—O4	−165.86 (11)
C3—C4—C5—C6	0.8 (3)	C8—C9—C10—O3	143.17 (16)
C7—C4—C5—C6	176.83 (19)	C8—C9—C10—O4	−38.69 (17)
C3—C4—C7—N1	81.02 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H4···O1i	0.907 (18)	2.315 (18)	3.1158 (15)	147.0 (13)
O2—H9···O1i	0.82	2.51	3.0673 (13)	127
O2—H9···N1i	0.82	1.99	2.7826 (16)	162
C11—H11A···O3ii	0.96	2.54	3.480 (2)	166
C11—H11C···O2iii	0.96	2.53	3.419 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H4⋯O1i	0.907 (18)	2.315 (18)	3.1158 (15)	147.0 (13)
O2—H9⋯O1i	0.82	2.51	3.0673 (13)	127
O2—H9⋯N1i	0.82	1.99	2.7826 (16)	162
C11—H11A⋯O3ii	0.96	2.54	3.480 (2)	166
C11—H11C⋯O2iii	0.96	2.53	3.419 (2)	154

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