[(3R*,4R*,5R*)-2,3-Diphenyl-isoxazolidine-4,5-di-yl]dimethanol.

In the title compound, C(17)H(19)NO(3), the isoxazolidine ring adopts an envelope conformation with the O atom as the flap. In the crystal, O-H⋯O hydrogen bonds form C(2) (3)(14) R(2) (2)(14) motifs.

Related literature

For general background to the preparation and use of compounds containing isoxazolidine rings, see: Agirbas et al. (2007 ▶); Kelly et al. (2009 ▶); Kumar et al. (2003 ▶); Kwon et al. (1995 ▶); Simonsen et al. (1999 ▶). For graph-set analysis of hydrogen-bonded networks, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For an alternative synthesis of the title compound, see: Tyukhteneva & Badovskaya (1992 ▶).

Experimental

Crystal data

C17H19NO3

M = 285.33

Orthorhombic,

a = 8.1254 (2) Å

b = 11.0602 (2) Å

c = 32.4813 (10) Å

V = 2919.05 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.68 × 0.28 × 0.03 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.985, T max = 0.997

35240 measured reflections

2687 independent reflections

1915 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.108

S = 1.12

2687 reflections

198 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812025032/ez2294sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812025032/ez2294Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025032/ez2294Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812025032/ez2294Isup4.cml

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

C17H19NO3	F(000) = 1216
Mr = 285.33	Dx = 1.299 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25949 reflections
a = 8.1254 (2) Å	θ = 1.3–26.2°
b = 11.0602 (2) Å	µ = 0.09 mm−1
c = 32.4813 (10) Å	T = 296 K
V = 2919.05 (13) Å3	Plate, colourless
Z = 8	0.68 × 0.28 × 0.03 mm

Stoe IPDS 2 diffractometer	2687 independent reflections
Radiation source: fine-focus sealed tube	1915 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
rotation method scans	θmax = 25.6°, θmin = 1.3°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −9→9
Tmin = 0.985, Tmax = 0.997	k = −12→12
35240 measured reflections	l = −39→39

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0399P)2 + 0.523P] where P = (Fo2 + 2Fc2)/3
2687 reflections	(Δ/σ)max < 0.001
198 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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
C1	0.4711 (2)	0.6940 (2)	0.11533 (6)	0.0398 (5)
C2	0.3582 (3)	0.7318 (2)	0.08617 (7)	0.0503 (6)
H2	0.3525	0.6929	0.0608	0.060*
C3	0.2538 (3)	0.8275 (2)	0.09473 (8)	0.0592 (7)
H3	0.1788	0.8526	0.0749	0.071*
C4	0.2587 (3)	0.8860 (2)	0.13183 (8)	0.0616 (7)
H4	0.1872	0.9496	0.1374	0.074*
C5	0.3716 (3)	0.8488 (3)	0.16085 (8)	0.0610 (7)
H5	0.3774	0.8885	0.1860	0.073*
C6	0.4761 (3)	0.7535 (2)	0.15292 (7)	0.0540 (6)
H6	0.5507	0.7288	0.1730	0.065*
C7	0.7547 (2)	0.6067 (2)	0.11543 (6)	0.0409 (5)
H7	0.7889	0.6870	0.1060	0.049*
C8	0.8016 (3)	0.5906 (2)	0.16002 (7)	0.0511 (6)
C9	0.7355 (3)	0.4976 (3)	0.18331 (7)	0.0678 (8)
H9	0.6590	0.4456	0.1715	0.081*
C10	0.7812 (4)	0.4808 (4)	0.22366 (9)	0.1015 (13)
H10	0.7354	0.4182	0.2390	0.122*
C11	0.8926 (6)	0.5553 (6)	0.24095 (12)	0.129 (2)
H11	0.9216	0.5439	0.2684	0.154*
C12	0.9637 (5)	0.6469 (5)	0.21928 (15)	0.1221 (17)
H12	1.0413	0.6969	0.2316	0.147*
C13	0.9181 (4)	0.6648 (3)	0.17780 (10)	0.0838 (10)
H13	0.9664	0.7264	0.1625	0.101*
C14	0.8311 (2)	0.50842 (19)	0.08718 (6)	0.0397 (5)
H14	0.8735	0.4437	0.1049	0.048*
C15	0.6801 (2)	0.4591 (2)	0.06423 (6)	0.0401 (5)
H15	0.6370	0.3897	0.0796	0.048*
C16	0.9726 (2)	0.5551 (2)	0.06155 (7)	0.0461 (6)
H16A	1.0594	0.5836	0.0796	0.055*
H16B	1.0168	0.4896	0.0450	0.055*
C17	0.6998 (3)	0.4225 (2)	0.01966 (6)	0.0458 (5)
H17A	0.5934	0.4004	0.0084	0.055*
H17B	0.7420	0.4903	0.0039	0.055*
N1	0.5745 (2)	0.59162 (16)	0.10899 (5)	0.0400 (4)
O1	0.56191 (16)	0.55449 (14)	0.06604 (4)	0.0442 (4)
O2	0.9219 (2)	0.65171 (15)	0.03502 (5)	0.0548 (5)
O3	0.80978 (19)	0.32278 (16)	0.01616 (5)	0.0491 (4)
H2A	1.003 (4)	0.667 (3)	0.0184 (9)	0.097 (11)*
H3A	0.757 (4)	0.260 (3)	0.0243 (9)	0.085 (10)*

	U11	U22	U33	U12	U13	U23
C1	0.0352 (10)	0.0386 (14)	0.0455 (11)	−0.0017 (9)	0.0046 (9)	0.0017 (10)
C2	0.0427 (11)	0.0530 (17)	0.0551 (13)	0.0039 (11)	−0.0043 (10)	−0.0042 (11)
C3	0.0432 (12)	0.0589 (18)	0.0756 (16)	0.0089 (12)	−0.0054 (12)	0.0019 (14)
C4	0.0475 (13)	0.0519 (17)	0.0855 (18)	0.0102 (12)	0.0134 (14)	−0.0037 (14)
C5	0.0607 (15)	0.0613 (19)	0.0610 (15)	0.0087 (13)	0.0095 (12)	−0.0122 (13)
C6	0.0541 (13)	0.0589 (18)	0.0489 (13)	0.0113 (12)	0.0017 (10)	−0.0040 (11)
C7	0.0357 (10)	0.0413 (13)	0.0457 (11)	−0.0019 (10)	0.0012 (9)	0.0007 (9)
C8	0.0432 (12)	0.0625 (18)	0.0477 (13)	0.0136 (12)	−0.0061 (10)	−0.0121 (11)
C9	0.0616 (15)	0.095 (2)	0.0466 (13)	0.0191 (15)	0.0036 (12)	0.0123 (14)
C10	0.082 (2)	0.170 (4)	0.0530 (17)	0.049 (2)	0.0043 (16)	0.020 (2)
C11	0.107 (3)	0.215 (6)	0.064 (2)	0.074 (4)	−0.028 (2)	−0.031 (3)
C12	0.098 (3)	0.153 (5)	0.114 (3)	0.033 (3)	−0.057 (3)	−0.064 (3)
C13	0.0696 (18)	0.091 (3)	0.091 (2)	0.0083 (17)	−0.0275 (16)	−0.0294 (18)
C14	0.0380 (10)	0.0374 (14)	0.0437 (11)	0.0024 (9)	0.0006 (9)	0.0026 (9)
C15	0.0410 (11)	0.0359 (13)	0.0433 (11)	0.0013 (10)	0.0031 (9)	0.0018 (9)
C16	0.0386 (11)	0.0431 (15)	0.0565 (13)	0.0047 (10)	0.0041 (10)	0.0040 (11)
C17	0.0473 (12)	0.0415 (15)	0.0485 (12)	0.0009 (10)	−0.0002 (9)	−0.0008 (10)
N1	0.0380 (9)	0.0433 (12)	0.0387 (9)	0.0015 (8)	−0.0003 (7)	−0.0041 (8)
O1	0.0426 (8)	0.0473 (10)	0.0427 (8)	0.0069 (7)	−0.0046 (6)	−0.0064 (7)
O2	0.0480 (9)	0.0482 (11)	0.0681 (10)	0.0066 (8)	0.0145 (8)	0.0167 (8)
O3	0.0481 (9)	0.0402 (11)	0.0590 (10)	0.0006 (8)	0.0111 (7)	−0.0021 (8)

C1—C2	1.383 (3)	C10—H10	0.9300
C1—C6	1.388 (3)	C11—C12	1.362 (6)
C1—N1	1.425 (3)	C11—H11	0.9300
C2—C3	1.385 (3)	C12—C13	1.411 (5)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.368 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C16	1.511 (3)
C4—C5	1.378 (3)	C14—C15	1.536 (3)
C4—H4	0.9300	C14—H14	0.9800
C5—C6	1.378 (3)	C15—O1	1.428 (2)
C5—H5	0.9300	C15—C17	1.512 (3)
C6—H6	0.9300	C15—H15	0.9800
C7—N1	1.488 (3)	C16—O2	1.433 (3)
C7—C8	1.508 (3)	C16—H16A	0.9700
C7—C14	1.552 (3)	C16—H16B	0.9700
C7—H7	0.9800	C17—O3	1.424 (3)
C8—C13	1.380 (4)	C17—H17A	0.9700
C8—C9	1.385 (4)	C17—H17B	0.9700
C9—C10	1.375 (4)	N1—O1	1.458 (2)
C9—H9	0.9300	O2—H2A	0.86 (3)
C10—C11	1.347 (6)	O3—H3A	0.86 (3)
C2—C1—C6	118.6 (2)	C11—C12—C13	119.1 (4)
C2—C1—N1	122.14 (19)	C11—C12—H12	120.5
C6—C1—N1	119.14 (19)	C13—C12—H12	120.5
C1—C2—C3	120.0 (2)	C8—C13—C12	119.8 (4)
C1—C2—H2	120.0	C8—C13—H13	120.1
C3—C2—H2	120.0	C12—C13—H13	120.1
C4—C3—C2	121.4 (2)	C16—C14—C15	117.50 (17)
C4—C3—H3	119.3	C16—C14—C7	113.01 (18)
C2—C3—H3	119.3	C15—C14—C7	102.49 (15)
C3—C4—C5	118.7 (2)	C16—C14—H14	107.8
C3—C4—H4	120.6	C15—C14—H14	107.8
C5—C4—H4	120.6	C7—C14—H14	107.8
C6—C5—C4	120.7 (2)	O1—C15—C17	107.96 (16)
C6—C5—H5	119.6	O1—C15—C14	104.74 (16)
C4—C5—H5	119.6	C17—C15—C14	118.40 (17)
C5—C6—C1	120.6 (2)	O1—C15—H15	108.5
C5—C6—H6	119.7	C17—C15—H15	108.5
C1—C6—H6	119.7	C14—C15—H15	108.5
N1—C7—C8	111.72 (17)	O2—C16—C14	111.57 (17)
N1—C7—C14	103.43 (16)	O2—C16—H16A	109.3
C8—C7—C14	112.57 (18)	C14—C16—H16A	109.3
N1—C7—H7	109.7	O2—C16—H16B	109.3
C8—C7—H7	109.7	C14—C16—H16B	109.3
C14—C7—H7	109.7	H16A—C16—H16B	108.0
C13—C8—C9	118.6 (2)	O3—C17—C15	110.49 (17)
C13—C8—C7	120.3 (3)	O3—C17—H17A	109.6
C9—C8—C7	120.9 (2)	C15—C17—H17A	109.6
C10—C9—C8	121.1 (3)	O3—C17—H17B	109.6
C10—C9—H9	119.5	C15—C17—H17B	109.6
C8—C9—H9	119.5	H17A—C17—H17B	108.1
C11—C10—C9	119.8 (4)	C1—N1—O1	108.72 (15)
C11—C10—H10	120.1	C1—N1—C7	118.06 (17)
C9—C10—H10	120.1	O1—N1—C7	103.59 (13)
C10—C11—C12	121.7 (4)	C15—O1—N1	101.56 (13)
C10—C11—H11	119.2	C16—O2—H2A	107 (2)
C12—C11—H11	119.2	C17—O3—H3A	107 (2)
C6—C1—C2—C3	0.3 (3)	N1—C7—C14—C15	6.3 (2)
N1—C1—C2—C3	176.2 (2)	C8—C7—C14—C15	127.02 (19)
C1—C2—C3—C4	−0.4 (4)	C16—C14—C15—O1	−101.0 (2)
C2—C3—C4—C5	0.7 (4)	C7—C14—C15—O1	23.48 (19)
C3—C4—C5—C6	−0.9 (4)	C16—C14—C15—C17	19.3 (3)
C4—C5—C6—C1	0.9 (4)	C7—C14—C15—C17	143.79 (19)
C2—C1—C6—C5	−0.5 (4)	C15—C14—C16—O2	58.9 (3)
N1—C1—C6—C5	−176.6 (2)	C7—C14—C16—O2	−60.2 (2)
N1—C7—C8—C13	−139.9 (2)	O1—C15—C17—O3	−176.79 (16)
C14—C7—C8—C13	104.2 (3)	C14—C15—C17—O3	64.6 (3)
N1—C7—C8—C9	43.5 (3)	C2—C1—N1—O1	10.9 (3)
C14—C7—C8—C9	−72.4 (3)	C6—C1—N1—O1	−173.18 (19)
C13—C8—C9—C10	1.7 (4)	C2—C1—N1—C7	128.4 (2)
C7—C8—C9—C10	178.3 (2)	C6—C1—N1—C7	−55.7 (3)
C8—C9—C10—C11	−0.3 (5)	C8—C7—N1—C1	85.1 (2)
C9—C10—C11—C12	−0.9 (6)	C14—C7—N1—C1	−153.59 (17)
C10—C11—C12—C13	0.7 (7)	C8—C7—N1—O1	−154.71 (17)
C9—C8—C13—C12	−1.8 (4)	C14—C7—N1—O1	−33.39 (19)
C7—C8—C13—C12	−178.5 (3)	C17—C15—O1—N1	−171.89 (16)
C11—C12—C13—C8	0.7 (6)	C14—C15—O1—N1	−44.85 (17)
N1—C7—C14—C16	133.72 (17)	C1—N1—O1—C15	175.74 (15)
C8—C7—C14—C16	−105.5 (2)	C7—N1—O1—C15	49.38 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3i	0.86 (3)	1.90 (3)	2.756 (2)	172 (3)
O3—H3A···O2ii	0.86 (3)	1.91 (3)	2.738 (2)	160 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3i	0.86 (3)	1.90 (3)	2.756 (2)	172 (3)
O3—H3A⋯O2ii	0.86 (3)	1.91 (3)	2.738 (2)	160 (3)

Symmetry codes: (i) ; (ii) .