(2S,3R,4R,5R)-3,4-Dihydr-oxy-5-(hydroxy-meth-yl)pyrrolidine-2-carboxylic acid [(2S,3R,4R,5R)-3,4-dihydr-oxy-5-(hydroxy-meth-yl)proline].

The crystal structure of the title compound, C(6)H(11)NO(5), establishes the relative configuration at the four stereogenic centres; the absolute configuration is determined by the use of d-glucuronolactone as the starting material for the synthesis. Mol-ecules are linked by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds into a three-dimensional network, with each mol-ecule acting as a donor and acceptor for five hydrogen bonds.

Related literature

For related literature on imino­sugars, see: Asano et al. (2000 ▶); Watson et al. (2001 ▶). For related literature on pipecolic acids, see: Fleet et al. (1987 ▶); Booth et al. (2007 ▶); Bashyal, Chow, Fellows & Fleet (1987 ▶); Manning et al. (1985 ▶); di Bello et al. (1984 ▶); Yoshimura et al. (2008 ▶). For related literature on bulgecinine, see: Toumi et al. (2008 ▶); Bashyal et al. (1986 ▶); Bashyal, Chow & Fleet (1987 ▶); Shinagawa et al. (1984 ▶, 1985 ▶). For related literature on alexines, see: Pereira et al. (1991 ▶); Donohoe et al. (2008 ▶); Kato et al. (2003 ▶); Wormald et al. (1998 ▶). For absolute configuration, see: Flack (1983 ▶); Flack & Bernardinelli (2000 ▶); Flack & Shmueli (2007 ▶); Hooft et al. (2008 ▶); Thompson et al. (2008 ▶); Watkin (1994 ▶). For the weighting scheme, see: Prince (1982 ▶); Thompson & Watkin (2009 ▶).

Experimental

Crystal data

C6H11NO5

M = 177.16

Triclinic,

a = 5.4160 (2) Å

b = 5.8236 (3) Å

c = 6.6006 (3) Å

α = 102.836 (2)°

β = 104.776 (2)°

γ = 102.8244 (19)°

V = 187.50 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.14 mm−1

T = 150 K

0.25 × 0.17 × 0.06 mm

Data collection

Area diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.94, T max = 0.99

2314 measured reflections

834 independent reflections

814 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.066

S = 1.00

834 reflections

109 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.17 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035636/lh2896sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035636/lh2896Isup2.hkl

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

C6H11NO5	Z = 1
Mr = 177.16	F(000) = 94
Triclinic, P1	Dx = 1.569 Mg m−3
Hall symbol: P 1	Melting point: not measured K
a = 5.4160 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.8236 (3) Å	Cell parameters from 696 reflections
c = 6.6006 (3) Å	θ = 5–27°
α = 102.836 (2)°	µ = 0.14 mm−1
β = 104.776 (2)°	T = 150 K
γ = 102.8244 (19)°	Plate, clear_pale_colourless
V = 187.50 (2) Å3	0.25 × 0.17 × 0.06 mm

Area diffractometer	814 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 5.6°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −7→7
Tmin = 0.94, Tmax = 0.99	k = −6→7
2314 measured reflections	l = −8→7
834 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027	H-atom parameters constrained
wR(F2) = 0.066	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 22.5 35.8 21.7 10.1 2.91
S = 1.00	(Δ/σ)max = 0.0001
834 reflections	Δρmax = 0.24 e Å−3
109 parameters	Δρmin = −0.17 e Å−3
3 restraints

	x	y	z	Uiso*/Ueq
O1	0.1323 (3)	0.4021 (3)	0.0397 (3)	0.0170
C2	0.3330 (4)	0.5769 (4)	0.1694 (3)	0.0124
O3	0.3285 (3)	0.7782 (3)	0.2816 (3)	0.0161
C4	0.6067 (4)	0.5299 (3)	0.1892 (3)	0.0118
N5	0.8297 (3)	0.7483 (3)	0.3462 (3)	0.0120
C6	0.8425 (4)	0.7309 (4)	0.5744 (3)	0.0130
C7	1.1277 (4)	0.8313 (4)	0.7284 (3)	0.0167
O8	1.2417 (3)	1.0809 (3)	0.7415 (3)	0.0209
C9	0.7092 (4)	0.4584 (4)	0.5443 (3)	0.0150
C10	0.6269 (4)	0.3243 (4)	0.2968 (3)	0.0135
O11	0.8192 (3)	0.2063 (3)	0.2544 (3)	0.0229
O12	0.4844 (4)	0.4511 (3)	0.6175 (3)	0.0252
H41	0.6365	0.4960	0.0477	0.0144*
H61	0.7333	0.8262	0.6278	0.0169*
H72	1.1284	0.8203	0.8747	0.0191*
H71	1.2343	0.7354	0.6770	0.0194*
H91	0.8360	0.3904	0.6257	0.0183*
H101	0.4566	0.2013	0.2549	0.0154*
H81	1.2048	1.1744	0.8368	0.0313*
H51	0.7954	0.8869	0.3332	0.0177*
H52	0.9817	0.7443	0.3204	0.0178*
H111	0.8993	0.2734	0.1839	0.0347*
H121	0.4206	0.3112	0.6224	0.0383*

	U11	U22	U33	U12	U13	U23
O1	0.0115 (7)	0.0187 (7)	0.0178 (7)	0.0024 (5)	0.0034 (5)	0.0030 (6)
C2	0.0128 (9)	0.0137 (9)	0.0134 (9)	0.0052 (7)	0.0051 (7)	0.0074 (7)
O3	0.0153 (7)	0.0148 (7)	0.0210 (7)	0.0075 (6)	0.0074 (5)	0.0057 (6)
C4	0.0113 (9)	0.0115 (8)	0.0130 (9)	0.0032 (7)	0.0050 (7)	0.0032 (7)
N5	0.0123 (8)	0.0098 (7)	0.0150 (8)	0.0039 (6)	0.0052 (6)	0.0042 (6)
C6	0.0142 (9)	0.0115 (8)	0.0136 (9)	0.0030 (7)	0.0053 (7)	0.0041 (7)
C7	0.0154 (9)	0.0161 (9)	0.0152 (9)	0.0013 (8)	0.0023 (7)	0.0042 (8)
O8	0.0246 (8)	0.0151 (8)	0.0190 (7)	−0.0019 (6)	0.0100 (6)	0.0020 (6)
C9	0.0173 (10)	0.0130 (9)	0.0165 (10)	0.0042 (7)	0.0066 (8)	0.0067 (7)
C10	0.0121 (9)	0.0124 (9)	0.0176 (9)	0.0049 (7)	0.0058 (7)	0.0050 (7)
O11	0.0280 (8)	0.0223 (8)	0.0356 (9)	0.0180 (7)	0.0218 (7)	0.0179 (7)
O12	0.0325 (9)	0.0164 (7)	0.0304 (9)	0.0018 (7)	0.0222 (8)	0.0056 (7)

O1—C2	1.264 (3)	C7—O8	1.421 (2)
C2—O3	1.249 (2)	C7—H72	0.981
C2—C4	1.545 (2)	C7—H71	0.959
C4—N5	1.498 (2)	O8—H81	0.832
C4—C10	1.532 (3)	C9—C10	1.545 (3)
C4—H41	0.972	C9—O12	1.415 (2)
N5—C6	1.517 (2)	C9—H91	0.972
N5—H51	0.885	C10—O11	1.420 (2)
N5—H52	0.886	C10—H101	0.963
C6—C7	1.515 (3)	O11—H111	0.816
C6—C9	1.535 (3)	O12—H121	0.823
C6—H61	0.973
O1—C2—O3	126.24 (18)	C6—C7—O8	111.22 (16)
O1—C2—C4	115.43 (17)	C6—C7—H72	108.8
O3—C2—C4	118.32 (17)	O8—C7—H72	109.4
C2—C4—N5	110.92 (15)	C6—C7—H71	109.8
C2—C4—C10	109.46 (14)	O8—C7—H71	108.5
N5—C4—C10	103.55 (15)	H72—C7—H71	109.1
C2—C4—H41	111.2	C7—O8—H81	110.0
N5—C4—H41	108.5	C6—C9—C10	106.41 (15)
C10—C4—H41	113.0	C6—C9—O12	106.33 (16)
C4—N5—C6	106.33 (14)	C10—C9—O12	111.81 (16)
C4—N5—H51	110.5	C6—C9—H91	110.0
C6—N5—H51	109.1	C10—C9—H91	109.3
C4—N5—H52	109.8	O12—C9—H91	112.7
C6—N5—H52	111.2	C9—C10—C4	103.65 (15)
H51—N5—H52	109.8	C9—C10—O11	109.89 (16)
N5—C6—C7	110.92 (15)	C4—C10—O11	113.98 (15)
N5—C6—C9	105.61 (15)	C9—C10—H101	108.3
C7—C6—C9	114.30 (16)	C4—C10—H101	111.8
N5—C6—H61	108.0	O11—C10—H101	109.0
C7—C6—H61	109.9	C10—O11—H111	110.0
C9—C6—H61	107.9	C9—O12—H121	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C7—H71···O12i	0.96	2.39	3.328 (3)	166
C10—H101···O3ii	0.96	2.47	3.199 (3)	133
O8—H81···O1iii	0.83	1.85	2.679 (3)	175
N5—H51···O11iv	0.88	2.03	2.873 (3)	160
N5—H52···O3i	0.89	1.93	2.814 (3)	173
O11—H111···O1i	0.82	1.89	2.696 (3)	170
O12—H121···O8v	0.82	1.91	2.668 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H81⋯O1i	0.83	1.85	2.679 (3)	175
N5—H51⋯O11ii	0.88	2.03	2.873 (3)	160
N5—H52⋯O3iii	0.89	1.93	2.814 (3)	173
O11—H111⋯O1iii	0.82	1.89	2.696 (3)	170
O12—H121⋯O8iv	0.82	1.91	2.668 (3)	154

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