(2R*,6S*)-tert-Butyl 2,6-bis-(hydroxy-meth-yl)morpholine-4-carboxyl-ate.

In the title compound, C(11)H(21)NO(5), the H atoms of the hydr-oxy groups are disordered over two positions, each in a 1:1 ratio. In the crystal, inter-molecular O-H⋯O hydrogen bonds link pairs of mol-ecules into centrosymmetric dimers. Weak inter-molecular O-H⋯O inter-actions further link these dimers into chains extended in the [100] direction.

Related literature

For details of the synthesis of 2,6-disubstituted morpholines, see: Dave & Sasaki (2004 ▶); Lupi et al. (2004 ▶).

Experimental

Crystal data

C11H21NO5

M = 247.29

Monoclinic,

a = 21.909 (3) Å

b = 5.6643 (8) Å

c = 22.510 (3) Å

β = 107.612 (3)°

V = 2662.5 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.45 × 0.34 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

6675 measured reflections

2476 independent reflections

1699 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.199

S = 1.06

2476 reflections

173 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017599/cv2712sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017599/cv2712Isup2.hkl

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

C11H21NO5	F(000) = 1072
Mr = 247.29	Dx = 1.234 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.909 (3) Å	Cell parameters from 1734 reflections
b = 5.6643 (8) Å	θ = 4.6–44.5°
c = 22.510 (3) Å	µ = 0.10 mm−1
β = 107.612 (3)°	T = 293 K
V = 2662.5 (7) Å3	Prismatic, colourless
Z = 8	0.45 × 0.34 × 0.21 mm

Bruker SMART CCD area-detector diffractometer	1699 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.086
graphite	θmax = 25.5°, θmin = 1.9°
φ and ω scans	h = −26→25
6675 measured reflections	k = −6→6
2476 independent reflections	l = −27→19

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0978P)2 + 0.9544P] where P = (Fo2 + 2Fc2)/3
2476 reflections	(Δ/σ)max = 0.028
173 parameters	Δρmax = 0.53 e Å−3
4 restraints	Δρmin = −0.38 e Å−3

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. 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 > 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	Occ. (<1)
O1	0.41734 (8)	1.2127 (3)	0.00900 (7)	0.0487 (5)
O2	0.33480 (10)	1.4453 (4)	−0.09361 (9)	0.0668 (6)
O3	0.53146 (9)	1.4619 (4)	0.06357 (9)	0.0638 (6)
O4	0.28864 (15)	0.7185 (5)	0.10144 (10)	0.1312 (14)
O5	0.38194 (9)	0.7747 (3)	0.17686 (8)	0.0598 (6)
N1	0.36921 (10)	0.9179 (4)	0.08274 (10)	0.0584 (6)
C1	0.34976 (12)	1.1868 (5)	−0.00456 (11)	0.0503 (7)
H1	0.3335	1.3098	0.0172	0.060*
C2	0.33469 (15)	0.9479 (5)	0.01673 (12)	0.0650 (8)
H2A	0.2890	0.9344	0.0102	0.078*
H2B	0.3472	0.8254	−0.0074	0.078*
C3	0.43769 (13)	0.9642 (5)	0.09948 (13)	0.0622 (8)
H3A	0.4584	0.8401	0.0829	0.075*
H3B	0.4558	0.9643	0.1445	0.075*
C4	0.44998 (11)	1.1985 (4)	0.07397 (10)	0.0477 (6)
H4	0.4348	1.3251	0.0956	0.057*
C5	0.32122 (14)	1.2194 (5)	−0.07387 (12)	0.0623 (8)
H5A	0.3381	1.0993	−0.0953	0.075*
H5B	0.2752	1.1985	−0.0851	0.075*
C6	0.51984 (12)	1.2342 (5)	0.08203 (12)	0.0566 (7)
H6A	0.5442	1.2103	0.1254	0.068*
H6B	0.5341	1.1185	0.0573	0.068*
C7	0.34176 (15)	0.7944 (5)	0.11901 (12)	0.0621 (8)
C8	0.36300 (13)	0.6503 (5)	0.22584 (11)	0.0527 (7)
C9	0.30285 (16)	0.7518 (6)	0.23374 (18)	0.0880 (11)
H9A	0.3061	0.9208	0.2358	0.132*
H9B	0.2968	0.6926	0.2715	0.132*
H9C	0.2670	0.7071	0.1989	0.132*
C10	0.3569 (2)	0.3929 (6)	0.21181 (18)	0.1117 (15)
H10A	0.3211	0.3662	0.1753	0.168*
H10B	0.3503	0.3098	0.2465	0.168*
H10C	0.3953	0.3367	0.2045	0.168*
C11	0.41842 (16)	0.7042 (7)	0.28251 (14)	0.0860 (11)
H11A	0.4570	0.6392	0.2773	0.129*
H11B	0.4108	0.6357	0.3186	0.129*
H11C	0.4230	0.8721	0.2878	0.129*
H2E	0.3751 (10)	1.474 (9)	−0.083 (2)	0.050 (15)*	0.50
H3E	0.5706 (11)	1.495 (9)	0.074 (3)	0.056 (16)*	0.50
H2D	0.303 (2)	1.529 (11)	−0.104 (3)	0.09 (3)*	0.50
H3D	0.507 (2)	1.477 (10)	0.0285 (13)	0.055 (16)*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0563 (11)	0.0596 (11)	0.0309 (9)	−0.0055 (8)	0.0143 (8)	0.0060 (7)
O2	0.0609 (14)	0.0802 (15)	0.0548 (12)	−0.0088 (12)	0.0109 (11)	0.0241 (11)
O3	0.0524 (12)	0.0870 (15)	0.0460 (12)	−0.0197 (10)	0.0059 (10)	0.0093 (10)
O4	0.147 (2)	0.169 (3)	0.0511 (13)	−0.123 (2)	−0.0095 (14)	0.0263 (15)
O5	0.0710 (12)	0.0721 (12)	0.0389 (10)	−0.0173 (9)	0.0205 (9)	0.0112 (8)
N1	0.0625 (14)	0.0725 (15)	0.0412 (12)	−0.0083 (11)	0.0172 (10)	0.0176 (11)
C1	0.0550 (15)	0.0575 (16)	0.0366 (13)	−0.0072 (12)	0.0113 (12)	0.0049 (11)
C2	0.083 (2)	0.0706 (19)	0.0403 (15)	−0.0186 (15)	0.0171 (14)	0.0078 (13)
C3	0.0615 (17)	0.0780 (19)	0.0519 (16)	0.0106 (14)	0.0243 (14)	0.0236 (14)
C4	0.0539 (15)	0.0601 (15)	0.0305 (12)	0.0048 (11)	0.0149 (11)	0.0068 (11)
C5	0.0687 (17)	0.0713 (18)	0.0415 (15)	−0.0159 (14)	0.0084 (13)	0.0121 (13)
C6	0.0551 (16)	0.0737 (19)	0.0406 (14)	0.0023 (13)	0.0143 (12)	0.0147 (13)
C7	0.086 (2)	0.0583 (16)	0.0398 (15)	−0.0304 (15)	0.0167 (14)	0.0014 (12)
C8	0.0714 (17)	0.0535 (15)	0.0382 (14)	−0.0117 (12)	0.0242 (13)	0.0085 (11)
C9	0.084 (2)	0.101 (3)	0.096 (3)	−0.0023 (18)	0.053 (2)	0.019 (2)
C10	0.212 (5)	0.0526 (19)	0.087 (3)	−0.011 (2)	0.070 (3)	0.0050 (19)
C11	0.087 (2)	0.119 (3)	0.0514 (18)	−0.0166 (19)	0.0197 (17)	0.0188 (18)

O1—C4	1.422 (3)	C3—H3A	0.9700
O1—C1	1.426 (3)	C3—H3B	0.9700
O2—C5	1.415 (3)	C4—C6	1.499 (3)
O2—H2E	0.858 (19)	C4—H4	0.9800
O2—H2D	0.82 (2)	C5—H5A	0.9700
O3—C6	1.402 (3)	C5—H5B	0.9700
O3—H3E	0.84 (2)	C6—H6A	0.9700
O3—H3D	0.817 (19)	C6—H6B	0.9700
O4—C7	1.191 (4)	C8—C10	1.489 (4)
O5—C7	1.338 (3)	C8—C9	1.497 (4)
O5—C8	1.470 (3)	C8—C11	1.503 (4)
N1—C7	1.347 (3)	C9—H9A	0.9600
N1—C3	1.456 (3)	C9—H9B	0.9600
N1—C2	1.459 (3)	C9—H9C	0.9600
C1—C2	1.505 (4)	C10—H10A	0.9600
C1—C5	1.506 (3)	C10—H10B	0.9600
C1—H1	0.9800	C10—H10C	0.9600
C2—H2A	0.9700	C11—H11A	0.9600
C2—H2B	0.9700	C11—H11B	0.9600
C3—C4	1.502 (4)	C11—H11C	0.9600
C4—O1—C1	112.38 (18)	C1—C5—H5A	109.2
C5—O2—H2E	112 (3)	O2—C5—H5B	109.2
C5—O2—H2D	112 (5)	C1—C5—H5B	109.2
H2E—O2—H2D	134 (6)	H5A—C5—H5B	107.9
C6—O3—H3E	113 (4)	O3—C6—C4	111.0 (2)
C6—O3—H3D	105 (4)	O3—C6—H6A	109.4
H3E—O3—H3D	125 (6)	C4—C6—H6A	109.4
C7—O5—C8	121.21 (19)	O3—C6—H6B	109.4
C7—N1—C3	123.4 (2)	C4—C6—H6B	109.4
C7—N1—C2	119.3 (2)	H6A—C6—H6B	108.0
C3—N1—C2	114.8 (2)	O4—C7—O5	125.6 (2)
O1—C1—C2	109.8 (2)	O4—C7—N1	123.9 (3)
O1—C1—C5	106.7 (2)	O5—C7—N1	110.5 (2)
C2—C1—C5	112.2 (2)	O5—C8—C10	109.7 (2)
O1—C1—H1	109.4	O5—C8—C9	111.3 (2)
C2—C1—H1	109.4	C10—C8—C9	112.0 (3)
C5—C1—H1	109.4	O5—C8—C11	101.6 (2)
N1—C2—C1	109.5 (2)	C10—C8—C11	112.1 (3)
N1—C2—H2A	109.8	C9—C8—C11	109.6 (3)
C1—C2—H2A	109.8	C8—C9—H9A	109.5
N1—C2—H2B	109.8	C8—C9—H9B	109.5
C1—C2—H2B	109.8	H9A—C9—H9B	109.5
H2A—C2—H2B	108.2	C8—C9—H9C	109.5
N1—C3—C4	110.5 (2)	H9A—C9—H9C	109.5
N1—C3—H3A	109.5	H9B—C9—H9C	109.5
C4—C3—H3A	109.6	C8—C10—H10A	109.5
N1—C3—H3B	109.6	C8—C10—H10B	109.5
C4—C3—H3B	109.5	H10A—C10—H10B	109.5
H3A—C3—H3B	108.1	C8—C10—H10C	109.5
O1—C4—C6	107.10 (19)	H10A—C10—H10C	109.5
O1—C4—C3	110.5 (2)	H10B—C10—H10C	109.5
C6—C4—C3	111.5 (2)	C8—C11—H11A	109.5
O1—C4—H4	109.2	C8—C11—H11B	109.5
C6—C4—H4	109.2	H11A—C11—H11B	109.5
C3—C4—H4	109.2	C8—C11—H11C	109.5
O2—C5—C1	112.0 (2)	H11A—C11—H11C	109.5
O2—C5—H5A	109.2	H11B—C11—H11C	109.5
C4—O1—C1—C2	−61.4 (3)	C2—C1—C5—O2	179.3 (2)
C4—O1—C1—C5	176.8 (2)	O1—C4—C6—O3	64.6 (3)
C7—N1—C2—C1	145.5 (3)	C3—C4—C6—O3	−174.3 (2)
C3—N1—C2—C1	−52.0 (3)	C8—O5—C7—O4	0.4 (5)
O1—C1—C2—N1	55.4 (3)	C8—O5—C7—N1	179.1 (2)
C5—C1—C2—N1	173.9 (2)	C3—N1—C7—O4	−165.7 (3)
C7—N1—C3—C4	−147.9 (3)	C2—N1—C7—O4	−4.8 (5)
C2—N1—C3—C4	50.5 (3)	C3—N1—C7—O5	15.6 (4)
C1—O1—C4—C6	−178.62 (19)	C2—N1—C7—O5	176.5 (2)
C1—O1—C4—C3	59.7 (3)	C7—O5—C8—C10	68.9 (4)
N1—C3—C4—O1	−52.3 (3)	C7—O5—C8—C9	−55.7 (3)
N1—C3—C4—C6	−171.3 (2)	C7—O5—C8—C11	−172.3 (3)
O1—C1—C5—O2	−60.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3D···O3i	0.82 (3)	2.02 (3)	2.809 (4)	164 (6)
O2—H2E···O3i	0.86 (3)	1.99 (3)	2.849 (3)	176 (5)
O2—H2D···O4ii	0.82 (4)	2.48 (5)	3.269 (4)	163 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3D⋯O3i	0.82 (3)	2.02 (3)	2.809 (4)	164 (6)
O2—H2E⋯O3i	0.86 (3)	1.99 (3)	2.849 (3)	176 (5)
O2—H2D⋯O4ii	0.82 (4)	2.48 (5)	3.269 (4)	163 (6)

Symmetry codes: (i) ; (ii) .