2,6-Dide-oxy-2,6-imino-l-glycero-d-ido-heptitol.

The title mol-ecule, C(7)H(15)NO(5), the major product from selective enzymatic oxidation followed by hydrogeno-lysis of the corresponding azido-heptitol, was found by X-ray crystallography to exisit in a chair conformation with three axial hydroxyl groups. One of the hydroxymethyl groups is disordered over two sets of sites in a 0.590 (3):0.410 (3) ratio. In the crystal, O-H⋯O, O-H⋯(O,O), O-H⋯N and N-H⋯O hydrogen bonding occurs.

Related literature

For the synthesis of homonojirimycin derivatives, see: Compain et al. (2009 ▶); Asano et al. (2000 ▶); Watson et al. (2001 ▶); Ikeda et al. (2000 ▶); Asano et al. (1998 ▶); Kite et al. (1988 ▶); Dondoni & Nuzzi (2006 ▶). For the biological applications of homonojirimycin derivatives, see: Compain et al. (2006 ▶). For related literature on Izumoring technology, see: Izumori et al. (2002 ▶, 2006 ▶); Yoshihara et al. (2008 ▶); Rao et al. (2008 ▶); Jones et al. (2008 ▶). For related crystallography literature, see: Görbitz (1999 ▶).

Experimental

Crystal data

C7H15NO5

M = 193.20

Monoclinic,

a = 10.2907 (3) Å

b = 7.6035 (3) Å

c = 11.0057 (3) Å

β = 91.8668 (16)°

V = 860.69 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 150 K

0.50 × 0.50 × 0.20 mm

Data collection

Area diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.81, T max = 0.98

7892 measured reflections

1944 independent reflections

1609 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 0.99

1944 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.32 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/S1600536809025045/lh2854sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025045/lh2854Isup2.hkl

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

C7H15NO5	F(000) = 416
Mr = 193.20	Dx = 1.491 Mg m−3
Monoclinic, P21/c	Melting point = 442–445 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.2907 (3) Å	Cell parameters from 1957 reflections
b = 7.6035 (3) Å	θ = 5–27°
c = 11.0057 (3) Å	µ = 0.13 mm−1
β = 91.8668 (16)°	T = 150 K
V = 860.69 (5) Å3	Block, colourless
Z = 4	0.50 × 0.50 × 0.20 mm

Area diffractometer	1609 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.5°, θmin = 5.2°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −13→13
Tmin = 0.81, Tmax = 0.98	k = −9→9
7892 measured reflections	l = −14→14
1944 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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(F2) + (0.04P)2 + 0.51P], where P = [max(Fo2,0) + 2Fc2]/3
S = 1.00	(Δ/σ)max = 0.0003
1944 reflections	Δρmax = 0.33 e Å−3
137 parameters	Δρmin = −0.32 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.80811 (11)	0.66935 (14)	0.76944 (10)	0.0174
C2	0.82099 (13)	0.48495 (17)	0.72876 (11)	0.0140
C3	0.81825 (12)	0.36103 (16)	0.83746 (11)	0.0123
C4	0.69637 (12)	0.38977 (18)	0.91183 (12)	0.0165
C5	0.68068 (13)	0.5840 (2)	0.94446 (13)	0.0224
C6	0.68515 (14)	0.69847 (18)	0.83143 (14)	0.0233	0.590 (3)
C7	0.6593 (4)	0.8833 (5)	0.8777 (4)	0.0176	0.590 (3)
O8	0.63068 (17)	0.9958 (2)	0.77658 (16)	0.0216	0.590 (3)
C9	0.68515 (14)	0.69847 (18)	0.83143 (14)	0.0233	0.410 (3)
C10	0.6878 (5)	0.9060 (7)	0.8365 (5)	0.0181	0.410 (3)
O11	0.5595 (2)	0.9664 (3)	0.8625 (2)	0.0216	0.410 (3)
O12	0.77676 (10)	0.63650 (15)	1.03344 (9)	0.0255
O13	0.58223 (9)	0.33556 (13)	0.84432 (9)	0.0203
O14	0.93148 (8)	0.39490 (12)	0.91177 (8)	0.0165
C15	0.94645 (14)	0.46860 (18)	0.66037 (12)	0.0197
O16	0.96317 (10)	0.29326 (13)	0.61694 (8)	0.0198
H21	0.7458	0.4528	0.6738	0.0157*
H31	0.8191	0.2378	0.8090	0.0130*
H41	0.7061	0.3208	0.9884	0.0187*
H61	0.6119	0.6629	0.7752	0.0259*	0.590 (3)
H72	0.7376	0.9276	0.9206	0.0197*	0.590 (3)
H71	0.5868	0.8832	0.9358	0.0206*	0.590 (3)
H91	0.6128	0.6622	0.7753	0.0259*	0.410 (3)
H101	0.7493	0.9437	0.9007	0.0210*	0.410 (3)
H102	0.7164	0.9563	0.7589	0.0216*	0.410 (3)
H152	1.0213	0.4990	0.7155	0.0218*
H151	0.9433	0.5524	0.5897	0.0228*
H141	0.9354	0.3293	0.9687	0.0234*
H161	1.0333	0.2501	0.6444	0.0297*
H51	0.5938	0.5992	0.9815	0.0254*
H11	0.8100	0.7367	0.7086	0.0211*
H131	0.5842	0.2333	0.8312	0.0306*
H121	0.8487	0.5930	1.0131	0.0367*
H81	0.5752	0.9542	0.7287	0.0322*	0.590 (3)
H111	0.5126	0.9323	0.8051	0.0290*	0.410 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0274 (6)	0.0091 (5)	0.0154 (5)	0.0007 (4)	−0.0047 (5)	0.0028 (4)
C2	0.0195 (6)	0.0112 (6)	0.0112 (6)	−0.0011 (5)	−0.0025 (5)	−0.0008 (5)
C3	0.0128 (6)	0.0108 (6)	0.0131 (6)	0.0006 (5)	−0.0020 (5)	0.0003 (5)
C4	0.0124 (6)	0.0209 (7)	0.0162 (6)	−0.0015 (5)	−0.0006 (5)	−0.0015 (5)
C5	0.0140 (6)	0.0270 (8)	0.0261 (7)	−0.0001 (5)	0.0015 (5)	−0.0142 (6)
C6	0.0182 (7)	0.0147 (7)	0.0360 (8)	0.0060 (5)	−0.0121 (6)	−0.0108 (6)
C7	0.0178 (18)	0.0121 (15)	0.0228 (19)	0.0025 (12)	−0.0007 (13)	−0.0022 (14)
O8	0.0237 (10)	0.0108 (8)	0.0296 (10)	0.0017 (7)	−0.0075 (8)	0.0001 (7)
C9	0.0182 (7)	0.0147 (7)	0.0360 (8)	0.0060 (5)	−0.0121 (6)	−0.0108 (6)
C10	0.016 (2)	0.011 (2)	0.027 (3)	0.0000 (17)	0.0016 (19)	−0.003 (2)
O11	0.0181 (13)	0.0185 (13)	0.0281 (14)	0.0063 (9)	−0.0002 (10)	−0.0055 (10)
O12	0.0200 (5)	0.0358 (6)	0.0207 (5)	−0.0033 (4)	0.0012 (4)	−0.0153 (4)
O13	0.0139 (5)	0.0153 (5)	0.0313 (5)	−0.0006 (4)	−0.0040 (4)	−0.0058 (4)
O14	0.0143 (5)	0.0191 (5)	0.0158 (4)	−0.0021 (4)	−0.0047 (3)	0.0067 (4)
C15	0.0268 (7)	0.0179 (7)	0.0147 (6)	−0.0055 (5)	0.0042 (5)	−0.0021 (5)
O16	0.0218 (5)	0.0215 (5)	0.0159 (4)	0.0025 (4)	−0.0009 (4)	−0.0073 (4)

N1—C2	1.4791 (16)	C7—O8	1.427 (4)
N1—C6	1.4738 (19)	C7—H72	0.981
N1—H11	0.844	C7—H71	0.998
C2—C3	1.5238 (17)	O8—H81	0.827
C2—C15	1.5206 (19)	C9—C10	1.579 (6)
C2—H21	0.997	C9—H91	0.991
C3—C4	1.5355 (17)	C10—O11	1.435 (6)
C3—O14	1.4251 (14)	C10—H101	0.976
C3—H31	0.988	C10—H102	0.989
C4—C5	1.5295 (19)	O11—H111	0.824
C4—O13	1.4300 (15)	O12—H121	0.847
C4—H41	0.995	O13—H131	0.791
C5—C6	1.520 (2)	O14—H141	0.801
C5—O12	1.4258 (16)	C15—O16	1.4286 (16)
C5—H51	1.002	C15—H152	0.992
C6—C7	1.521 (4)	C15—H151	1.005
C6—H61	0.997	O16—H161	0.840
C2—N1—C6	111.67 (10)	C7—C6—H61	108.8
C2—N1—H11	109.3	C6—C7—O8	109.1 (3)
C6—N1—H11	108.6	C6—C7—H72	109.2
N1—C2—C3	110.14 (10)	O8—C7—H72	108.4
N1—C2—C15	108.25 (10)	C6—C7—H71	110.9
C3—C2—C15	112.07 (11)	O8—C7—H71	111.1
N1—C2—H21	109.9	H72—C7—H71	108.1
C3—C2—H21	106.9	C7—O8—H81	112.8
C15—C2—H21	109.6	C5—C9—N1	110.01 (11)
C2—C3—C4	111.52 (10)	C5—C9—C10	123.0 (2)
C2—C3—O14	107.64 (10)	N1—C9—C10	98.8 (2)
C4—C3—O14	109.59 (10)	C5—C9—H91	108.0
C2—C3—H31	109.7	N1—C9—H91	108.0
C4—C3—H31	108.6	C10—C9—H91	108.2
O14—C3—H31	109.8	C9—C10—O11	108.2 (4)
C3—C4—C5	110.91 (11)	C9—C10—H101	109.2
C3—C4—O13	110.69 (10)	O11—C10—H101	110.0
C5—C4—O13	108.00 (11)	C9—C10—H102	111.2
C3—C4—H41	108.4	O11—C10—H102	110.4
C5—C4—H41	108.6	H101—C10—H102	107.9
O13—C4—H41	110.3	C10—O11—H111	105.5
C4—C5—C6	110.76 (11)	C5—O12—H121	107.5
C4—C5—O12	110.82 (12)	C4—O13—H131	110.7
C6—C5—O12	111.27 (12)	C3—O14—H141	110.9
C4—C5—H51	108.0	C2—C15—O16	110.82 (11)
C6—C5—H51	108.6	C2—C15—H152	109.5
O12—C5—H51	107.2	O16—C15—H152	108.8
C5—C6—N1	110.01 (11)	C2—C15—H151	108.9
C5—C6—C7	104.18 (18)	O16—C15—H151	109.5
N1—C6—C7	117.11 (18)	H152—C15—H151	109.3
C5—C6—H61	108.1	C15—O16—H161	110.8
N1—C6—H61	108.3

D—H···A	D—H	H···A	D···A	D—H···A
O11—H71···C5	1.06	2.47	3.279 (3)	132
O8—H102···N1	0.96	2.38	3.084 (3)	130
O14—H141···O16i	0.80	1.89	2.684 (3)	170
O16—H161···N1ii	0.84	1.96	2.793 (3)	171
N1—H11···O12iii	0.84	2.17	2.996 (3)	165
O13—H131···O8iv	0.79	1.97	2.739 (3)	165
O13—H131···O11iv	0.79	2.08	2.824 (3)	158
O12—H121···O14	0.85	2.07	2.800 (3)	143
O12—H121···O14v	0.85	2.39	3.052 (3)	136
O8—H81···O13vi	0.83	2.00	2.805 (3)	164
O11—H111···O13vi	0.82	2.02	2.843 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O14—H141⋯O16i	0.80	1.89	2.684 (3)	170
O16—H161⋯N1ii	0.84	1.96	2.793 (3)	171
N1—H11⋯O12iii	0.84	2.17	2.996 (3)	165
O13—H131⋯O8iv	0.79	1.97	2.739 (3)	165
O13—H131⋯O11iv	0.79	2.08	2.824 (3)	158
O12—H121⋯O14v	0.85	2.39	3.052 (3)	136
O8—H81⋯O13vi	0.83	2.00	2.805 (3)	164
O11—H111⋯O13vi	0.82	2.02	2.843 (3)	173

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