(1S,2R,6R,7aS)-1,2,6-Trihy-droxy-hexa-hydro-1H-pyrrolizin-3-one.

In the title compound, C(7)H(11)NO(4), prepared via a Morita-Baylis-Hillman adduct, the five-membered ring bearing three O atoms approximates to a twisted conformation, whereas the other ring is close to an envelope, with a C atom in the flap position. The dihedral angle between their mean planes (all atoms) is 23.11 (9)°. The new stereocenters are created in a trans-diaxial configuration. In the crystal, O-H⋯O and O-H⋯(O,O) hydrogen bonds link the mol-ecules, generating a three-dimensional network. A weak C-H⋯O inter-action also occurs.

Related literature

For the utilization of this type of pyrrolizidinone as an inihibitor of glicosidase, see: D’Alanzo et al. (2009) ▶; Ayad et al. (2004 ▶) and for their huge therapeutical potential for the treatment of a number of diseases such as cancer, diabetes, and lysosomal storage disorders, see: Baumann (2007 ▶). For related literature concerning preparation of the title compound, see: Freire et al. (2007 ▶). Analysis of the absolute structure was also performed using likelihood methods, see: Hooft et al. (2008 ▶).

Experimental

Crystal data

C7H11NO4

M = 173.17

Monoclinic,

a = 4.6983 (3) Å

b = 14.5424 (10) Å

c = 5.5271 (4) Å

β = 99.663 (3)°

V = 372.28 (4) Å3

Z = 2

Cu Kα radiation

μ = 1.09 mm−1

T = 100 K

0.31 × 0.27 × 0.25 mm

Data collection

Bruker Kappa APEXII DUO diffractometer

3697 measured reflections

1229 independent reflections

1228 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.073

S = 1.14

1229 reflections

112 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.41 e Å−3

Absolute structure: Flack (1983 ▶), 537 Friedel pairs

Flack parameter: 0.20 (17)

Data collection: APEX2 (Bruker, 2010) ▶; cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: WinGX (Farrugia,1999 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002292/hb6566sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002292/hb6566Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002292/hb6566Isup3.cml

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

C7H11NO4	F(000) = 184
Mr = 173.17	Dx = 1.545 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 4.6983 (3) Å	Cell parameters from 1229 reflections
b = 14.5424 (10) Å	θ = 6.1–66.8°
c = 5.5271 (4) Å	µ = 1.09 mm−1
β = 99.663 (3)°	T = 100 K
V = 372.28 (4) Å3	Rectangular block, colorless
Z = 2	0.31 × 0.27 × 0.25 mm

Bruker Kappa APEXII DUO diffractometer	1228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 66.8°, θmin = 6.1°
Bruker APEX CCD area–detector scans	h = −5→5
3697 measured reflections	k = −16→16
1229 independent reflections	l = −6→6

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.0546P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.012
1229 reflections	Δρmax = 0.27 e Å−3
112 parameters	Δρmin = −0.41 e Å−3
1 restraint	Absolute structure: Flack (1983), 537 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.20 (17)

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
O1	0.6971 (2)	−0.03528 (7)	0.86162 (19)	0.0163 (3)
H1	0.7222	−0.0594	1.0016	0.024*
O2	0.2633 (2)	0.38620 (8)	0.6676 (2)	0.0167 (3)
H2	0.1802	0.4123	0.5394	0.025*
O3	0.9071 (2)	0.13035 (8)	1.12983 (19)	0.0194 (3)
O4	0.1530 (2)	0.02523 (7)	0.5015 (2)	0.0167 (3)
H4	0.0715	0.0504	0.3714	0.025*
N1	0.5577 (3)	0.20182 (9)	0.8573 (2)	0.0128 (3)
C1	0.5216 (3)	0.04341 (11)	0.8610 (3)	0.0134 (3)
H1A	0.3599	0.0303	0.9528	0.016*
C2	0.6890 (3)	0.12859 (11)	0.9697 (3)	0.0141 (3)
C3	0.6663 (3)	0.29584 (11)	0.8577 (3)	0.0143 (3)
H3A	0.8780	0.2966	0.8633	0.017*
H3B	0.6191	0.3310	0.9992	0.017*
C4	0.5078 (3)	0.33520 (10)	0.6142 (3)	0.0136 (3)
H4A	0.6384	0.3753	0.5346	0.016*
C5	0.4128 (3)	0.25050 (10)	0.4564 (3)	0.0142 (3)
H5A	0.2409	0.2644	0.3318	0.017*
H5B	0.5701	0.2286	0.3721	0.017*
C6	0.3420 (3)	0.17927 (10)	0.6401 (2)	0.0124 (3)
H6	0.1420	0.1887	0.6752	0.015*
C7	0.3995 (3)	0.07635 (12)	0.6019 (3)	0.0132 (3)
H7	0.5501	0.0697	0.4949	0.016*

	U11	U22	U33	U12	U13	U23
O1	0.0237 (5)	0.0097 (6)	0.0144 (5)	0.0043 (5)	0.0003 (4)	0.0025 (5)
O2	0.0219 (5)	0.0113 (6)	0.0152 (5)	0.0040 (4)	−0.0017 (4)	0.0004 (4)
O3	0.0229 (6)	0.0171 (6)	0.0149 (5)	0.0001 (5)	−0.0062 (4)	0.0016 (4)
O4	0.0209 (5)	0.0118 (6)	0.0141 (5)	−0.0016 (4)	−0.0065 (4)	0.0014 (4)
N1	0.0192 (6)	0.0101 (6)	0.0077 (6)	0.0004 (5)	−0.0019 (5)	−0.0002 (5)
C1	0.0175 (7)	0.0110 (7)	0.0111 (8)	0.0019 (6)	0.0007 (6)	0.0014 (5)
C2	0.0196 (7)	0.0140 (8)	0.0086 (7)	−0.0004 (6)	0.0021 (6)	−0.0007 (6)
C3	0.0172 (7)	0.0116 (8)	0.0130 (7)	−0.0010 (6)	−0.0009 (6)	−0.0009 (6)
C4	0.0185 (8)	0.0093 (7)	0.0124 (7)	0.0001 (6)	0.0007 (6)	0.0006 (5)
C5	0.0213 (7)	0.0106 (8)	0.0097 (7)	0.0001 (6)	−0.0005 (6)	0.0014 (6)
C6	0.0152 (7)	0.0113 (8)	0.0098 (7)	0.0010 (6)	−0.0005 (6)	0.0003 (6)
C7	0.0151 (7)	0.0120 (7)	0.0114 (7)	0.0002 (6)	−0.0007 (6)	0.0020 (6)

O1—C1	1.410 (2)	C1—H1A	1.0000
O1—H1	0.8400	C3—C4	1.535 (2)
O2—C4	1.439 (2)	C3—H3A	0.9900
O2—H2	0.8400	C3—H3B	0.9900
O3—C2	1.2368 (19)	C4—C5	1.532 (2)
O4—C7	1.409 (2)	C4—H4A	1.0000
O4—H4	0.8400	C5—C6	1.526 (2)
N1—C2	1.331 (2)	C5—H5A	0.9900
N1—C3	1.459 (2)	C5—H5B	0.9900
N1—C6	1.4721 (18)	C6—C7	1.542 (2)
C1—C7	1.528 (2)	C6—H6	1.0000
C1—C2	1.535 (2)	C7—H7	1.0000
C1—O1—H1	109.5	C5—C4—C3	104.56 (12)
C4—O2—H2	109.5	O2—C4—H4A	111.1
C7—O4—H4	109.5	C5—C4—H4A	111.1
C2—N1—C3	127.91 (12)	C3—C4—H4A	111.1
C2—N1—C6	113.83 (12)	C6—C5—C4	104.01 (12)
C3—N1—C6	113.74 (12)	C6—C5—H5A	111.0
O1—C1—C7	112.59 (13)	C4—C5—H5A	111.0
O1—C1—C2	113.15 (12)	C6—C5—H5B	111.0
C7—C1—C2	101.60 (12)	C4—C5—H5B	111.0
O1—C1—H1A	109.7	H5A—C5—H5B	109.0
C7—C1—H1A	109.7	N1—C6—C5	101.20 (12)
C2—C1—H1A	109.7	N1—C6—C7	102.44 (12)
O3—C2—N1	125.51 (15)	C5—C6—C7	120.32 (12)
O3—C2—C1	127.26 (14)	N1—C6—H6	110.6
N1—C2—C1	107.22 (11)	C5—C6—H6	110.6
N1—C3—C4	103.30 (12)	C7—C6—H6	110.6
N1—C3—H3A	111.1	O4—C7—C1	110.98 (13)
C4—C3—H3A	111.1	O4—C7—C6	114.49 (13)
N1—C3—H3B	111.1	C1—C7—C6	102.87 (12)
C4—C3—H3B	111.1	O4—C7—H7	109.4
H3A—C3—H3B	109.1	C1—C7—H7	109.4
O2—C4—C5	111.40 (12)	C6—C7—H7	109.4
O2—C4—C3	107.38 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.98	2.8190 (15)	174
O2—H2···O1ii	0.84	2.50	3.1745 (15)	138
O2—H2···O4iii	0.84	2.25	2.8589 (15)	129
O4—H4···O3iv	0.84	1.84	2.6636 (15)	167
C4—H4A···O4ii	1.00	2.41	3.3057 (18)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	1.98	2.8190 (15)	174
O2—H2⋯O1ii	0.84	2.50	3.1745 (15)	138
O2—H2⋯O4iii	0.84	2.25	2.8589 (15)	129
O4—H4⋯O3iv	0.84	1.84	2.6636 (15)	167
C4—H4A⋯O4ii	1.00	2.41	3.3057 (18)	148

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