1,2;5,6-Di-O-isopropyl-idene-3-C-nitro-methyl-α-d-allofuran-ose.

The mol-ecule of the title compound, C(13)H(21)NO(8), consists of two methyl-enedi-oxy rings and one tetra-hydro-furan ring. In the crystal, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into helical chains running along the 6(1) screw axis. Weak inter-molecular C-H⋯O hydrogen bonds help to stabilize the crystal packing. Voids of 245 Å(3) per unit cell occur.

Related literature

For details of the synthesis, see: Saito et al. (2002 ▶). For recent studies of the biological activity of aza­sugars, see: Loiseleur et al. (2007 ▶); Rahman et al. (2008 ▶).

Experimental

Crystal data

C13H21NO8

M = 319.31

Hexagonal,

a = 13.2581 (19) Å

c = 16.462 (3) Å

V = 2506.0 (7) Å3

Z = 6

Mo Kα radiation

μ = 0.11 mm−1

T = 291 K

0.24 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS-IV diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.975, T max = 0.979

8380 measured reflections

1612 independent reflections

1534 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.164

S = 1.08

1612 reflections

205 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.26 e Å−3

Data collection: R-AXIS-IV Software (Rigaku, 1997 ▶); cell refinement: R-AXIS-IV Software; data reduction: R-AXIS-IV Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: TEXSAN (Molecular Structure Corporation, 1992 ▶); software used to prepare material for publication: TEXSAN.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017314/cv5090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017314/cv5090Isup2.hkl

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

C13H21NO8	Dx = 1.270 Mg m−3
Mr = 319.31	Melting point = 383–384 K
Hexagonal, P61	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 61	Cell parameters from 398 reflections
a = 13.2581 (19) Å	θ = 2–25.1°
c = 16.462 (3) Å	µ = 0.11 mm−1
V = 2506.0 (7) Å3	T = 291 K
Z = 6	Prismatic, colourless
F(000) = 1020	0.24 × 0.20 × 0.20 mm

Rigaku R-AXIS-IV diffractometer	1612 independent reflections
Radiation source: fine-focus sealed tube	1534 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 0 pixels mm-1	θmax = 25.5°, θmin = 1.8°
Oscillation frames scans	h = −13→16
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −16→0
Tmin = 0.975, Tmax = 0.979	l = −19→19
8380 measured reflections

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)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.164	w = 1/[σ2(Fo2) + (0.0962P)2 + 1.0744P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1612 reflections	Δρmax = 0.43 e Å−3
205 parameters	Δρmin = −0.26 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

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	0.2338 (3)	0.7097 (4)	0.2334 (2)	0.0565 (10)
O2	0.0552 (3)	0.6458 (3)	0.1793 (2)	0.0427 (8)
O3	0.0092 (2)	0.5408 (3)	0.0319 (2)	0.0405 (7)
O4	0.3029 (3)	0.6935 (3)	0.1082 (2)	0.0490 (9)
O5	0.1802 (3)	0.4394 (3)	−0.0205 (3)	0.0597 (11)
O6	0.3601 (3)	0.4537 (4)	−0.0197 (3)	0.0557 (9)
O7	0.0437 (7)	0.7865 (7)	−0.0252 (4)	0.127 (3)
O8	0.0234 (7)	0.6912 (7)	−0.1261 (4)	0.131 (3)
N1	0.0764 (5)	0.7349 (5)	−0.0646 (3)	0.0639 (13)
C1	0.2559 (4)	0.7508 (4)	0.1523 (3)	0.0472 (12)
H1A	0.3068	0.8355	0.1502	0.057*
C2	0.1347 (4)	0.7135 (4)	0.1170 (3)	0.0417 (10)
H2A	0.1263	0.7800	0.1005	0.050*
C3	0.1227 (4)	0.6337 (4)	0.0451 (3)	0.0358 (9)
C4	0.2095 (3)	0.5932 (4)	0.0705 (3)	0.0362 (10)
H4A	0.1721	0.5317	0.1114	0.043*
C5	0.2641 (4)	0.5535 (5)	0.0066 (3)	0.0445 (11)
H5A	0.2918	0.6081	−0.0392	0.053*
C6	0.3605 (5)	0.5349 (5)	0.0379 (3)	0.0514 (12)
H6A	0.4347	0.6070	0.0381	0.062*
H6B	0.3438	0.5025	0.0923	0.062*
C7	0.1610 (4)	0.7012 (5)	−0.0346 (3)	0.0496 (12)
H7A	0.2360	0.7709	−0.0268	0.059*
H7B	0.1703	0.6537	−0.0754	0.059*
C8	0.1192 (4)	0.6842 (5)	0.2544 (3)	0.0463 (12)
C9	0.0671 (6)	0.5833 (6)	0.3133 (4)	0.0650 (15)
H9A	0.0672	0.5174	0.2892	0.097*
H9B	−0.0114	0.5635	0.3258	0.097*
H9C	0.1125	0.6050	0.3623	0.097*
C10	0.1218 (6)	0.7930 (6)	0.2860 (4)	0.0693 (17)
H10A	0.1542	0.8528	0.2453	0.104*
H10B	0.1689	0.8196	0.3341	0.104*
H10C	0.0440	0.7755	0.2986	0.104*
C11	0.2428 (4)	0.3839 (5)	−0.0501 (4)	0.0552 (13)
C12	0.1872 (7)	0.2647 (6)	−0.0156 (6)	0.093 (2)
H12A	0.1886	0.2690	0.0426	0.139*
H12B	0.2291	0.2269	−0.0332	0.139*
H12C	0.1080	0.2210	−0.0340	0.139*
C13	0.2482 (6)	0.3881 (7)	−0.1415 (4)	0.0729 (19)
H13A	0.2860	0.4677	−0.1592	0.109*
H13B	0.1707	0.3469	−0.1632	0.109*
H13C	0.2915	0.3523	−0.1602	0.109*
H3E	−0.017 (6)	0.497 (6)	0.077 (5)	0.067 (19)*

	U11	U22	U33	U12	U13	U23
O1	0.0408 (19)	0.077 (3)	0.0453 (19)	0.0249 (17)	−0.0092 (15)	−0.0111 (18)
O2	0.0312 (16)	0.0491 (19)	0.0426 (17)	0.0161 (15)	−0.0026 (13)	−0.0029 (14)
O3	0.0244 (15)	0.0419 (17)	0.0460 (17)	0.0098 (14)	−0.0045 (13)	0.0004 (15)
O4	0.0269 (16)	0.057 (2)	0.054 (2)	0.0135 (14)	−0.0040 (14)	−0.0109 (16)
O5	0.0323 (17)	0.066 (2)	0.075 (2)	0.0197 (16)	−0.0017 (17)	−0.028 (2)
O6	0.045 (2)	0.071 (2)	0.059 (2)	0.0357 (19)	0.0046 (17)	−0.0059 (19)
O7	0.193 (8)	0.185 (7)	0.089 (4)	0.159 (7)	−0.029 (4)	−0.013 (5)
O8	0.173 (6)	0.184 (7)	0.094 (4)	0.132 (6)	−0.057 (5)	−0.031 (5)
N1	0.095 (4)	0.069 (3)	0.044 (3)	0.053 (3)	−0.006 (3)	0.003 (2)
C1	0.033 (2)	0.041 (3)	0.056 (3)	0.010 (2)	−0.005 (2)	−0.010 (2)
C2	0.037 (2)	0.037 (2)	0.047 (3)	0.016 (2)	−0.003 (2)	0.002 (2)
C3	0.029 (2)	0.034 (2)	0.040 (2)	0.0126 (18)	−0.0018 (17)	0.0001 (18)
C4	0.026 (2)	0.040 (2)	0.035 (2)	0.0113 (18)	−0.0010 (17)	0.0023 (18)
C5	0.034 (2)	0.054 (3)	0.043 (2)	0.020 (2)	0.0006 (19)	−0.002 (2)
C6	0.044 (3)	0.067 (3)	0.047 (3)	0.031 (3)	0.000 (2)	−0.008 (3)
C7	0.041 (3)	0.058 (3)	0.046 (3)	0.022 (2)	0.003 (2)	0.011 (2)
C8	0.035 (2)	0.055 (3)	0.043 (3)	0.018 (2)	−0.0061 (19)	−0.011 (2)
C9	0.063 (4)	0.077 (4)	0.050 (3)	0.031 (3)	−0.006 (3)	0.003 (3)
C10	0.067 (4)	0.070 (4)	0.067 (4)	0.031 (3)	0.004 (3)	−0.019 (3)
C11	0.044 (3)	0.064 (3)	0.059 (3)	0.027 (3)	0.012 (2)	−0.010 (3)
C12	0.093 (5)	0.065 (4)	0.106 (6)	0.028 (4)	0.033 (5)	0.000 (4)
C13	0.060 (3)	0.105 (5)	0.061 (3)	0.047 (4)	−0.005 (3)	−0.023 (4)

O1—C1	1.415 (7)	C5—C6	1.509 (7)
O1—C8	1.424 (6)	C5—H5A	0.9800
O2—C2	1.421 (6)	C6—H6A	0.9700
O2—C8	1.441 (6)	C6—H6B	0.9700
O3—C3	1.405 (5)	C7—H7A	0.9700
O3—H3E	0.90 (8)	C7—H7B	0.9700
O4—C1	1.402 (6)	C8—C9	1.510 (8)
O4—C4	1.428 (5)	C8—C10	1.517 (8)
O5—C5	1.429 (6)	C9—H9A	0.9600
O5—C11	1.441 (6)	C9—H9B	0.9600
O6—C6	1.432 (6)	C9—H9C	0.9600
O6—C11	1.445 (7)	C10—H10A	0.9600
O7—N1	1.171 (8)	C10—H10B	0.9600
O8—N1	1.204 (8)	C10—H10C	0.9600
N1—C7	1.484 (7)	C11—C12	1.483 (10)
C1—C2	1.540 (7)	C11—C13	1.506 (9)
C1—H1A	0.9800	C12—H12A	0.9600
C2—C3	1.542 (7)	C12—H12B	0.9600
C2—H2A	0.9800	C12—H12C	0.9600
C3—C7	1.525 (7)	C13—H13A	0.9600
C3—C4	1.551 (6)	C13—H13B	0.9600
C4—C5	1.513 (6)	C13—H13C	0.9600
C4—H4A	0.9800
C1—O1—C8	108.2 (4)	H6A—C6—H6B	109.2
C2—O2—C8	106.1 (3)	N1—C7—C3	112.5 (4)
C3—O3—H3E	110 (4)	N1—C7—H7A	109.1
C1—O4—C4	108.4 (3)	C3—C7—H7A	109.1
C5—O5—C11	107.7 (4)	N1—C7—H7B	109.1
C6—O6—C11	108.0 (4)	C3—C7—H7B	109.1
O7—N1—O8	116.7 (7)	H7A—C7—H7B	107.8
O7—N1—C7	123.3 (5)	O1—C8—O2	104.1 (4)
O8—N1—C7	118.8 (6)	O1—C8—C9	109.1 (4)
O4—C1—O1	110.1 (4)	O2—C8—C9	108.1 (4)
O4—C1—C2	107.8 (4)	O1—C8—C10	110.0 (4)
O1—C1—C2	104.5 (4)	O2—C8—C10	111.1 (5)
O4—C1—H1A	111.4	C9—C8—C10	113.9 (5)
O1—C1—H1A	111.4	C8—C9—H9A	109.5
C2—C1—H1A	111.4	C8—C9—H9B	109.5
O2—C2—C1	104.8 (4)	H9A—C9—H9B	109.5
O2—C2—C3	109.3 (4)	C8—C9—H9C	109.5
C1—C2—C3	104.0 (4)	H9A—C9—H9C	109.5
O2—C2—H2A	112.7	H9B—C9—H9C	109.5
C1—C2—H2A	112.7	C8—C10—H10A	109.5
C3—C2—H2A	112.7	C8—C10—H10B	109.5
O3—C3—C7	106.1 (4)	H10A—C10—H10B	109.5
O3—C3—C2	114.6 (4)	C8—C10—H10C	109.5
C7—C3—C2	111.6 (4)	H10A—C10—H10C	109.5
O3—C3—C4	113.2 (3)	H10B—C10—H10C	109.5
C7—C3—C4	110.4 (4)	O5—C11—O6	105.5 (4)
C2—C3—C4	101.0 (3)	O5—C11—C12	108.0 (5)
O4—C4—C5	106.5 (3)	O6—C11—C12	110.6 (6)
O4—C4—C3	104.1 (3)	O5—C11—C13	110.4 (6)
C5—C4—C3	119.9 (4)	O6—C11—C13	107.8 (5)
O4—C4—H4A	108.6	C12—C11—C13	114.2 (6)
C5—C4—H4A	108.6	C11—C12—H12A	109.5
C3—C4—H4A	108.6	C11—C12—H12B	109.5
O5—C5—C6	102.0 (4)	H12A—C12—H12B	109.5
O5—C5—C4	109.4 (4)	C11—C12—H12C	109.5
C6—C5—C4	114.2 (4)	H12A—C12—H12C	109.5
O5—C5—H5A	110.3	H12B—C12—H12C	109.5
C6—C5—H5A	110.3	C11—C13—H13A	109.5
C4—C5—H5A	110.3	C11—C13—H13B	109.5
O6—C6—C5	102.2 (4)	H13A—C13—H13B	109.5
O6—C6—H6A	111.3	C11—C13—H13C	109.5
C5—C6—H6A	111.3	H13A—C13—H13C	109.5
O6—C6—H6B	111.3	H13B—C13—H13C	109.5
C5—C6—H6B	111.3
C4—O4—C1—O1	91.7 (4)	C11—O5—C5—C4	−154.2 (4)
C4—O4—C1—C2	−21.7 (5)	O4—C4—C5—O5	166.8 (4)
C8—O1—C1—O4	−132.3 (4)	C3—C4—C5—O5	−75.7 (5)
C8—O1—C1—C2	−16.8 (5)	O4—C4—C5—C6	53.2 (5)
C8—O2—C2—C1	24.8 (5)	C3—C4—C5—C6	170.8 (4)
C8—O2—C2—C3	135.8 (4)	C11—O6—C6—C5	−29.7 (6)
O4—C1—C2—O2	111.9 (4)	O5—C5—C6—O6	37.9 (5)
O1—C1—C2—O2	−5.2 (5)	C4—C5—C6—O6	155.7 (4)
O4—C1—C2—C3	−2.9 (5)	O7—N1—C7—C3	53.9 (9)
O1—C1—C2—C3	−119.9 (4)	O8—N1—C7—C3	−112.8 (7)
O2—C2—C3—O3	34.0 (5)	O3—C3—C7—N1	53.1 (6)
C1—C2—C3—O3	145.5 (4)	C2—C3—C7—N1	−72.5 (5)
O2—C2—C3—C7	154.7 (4)	C4—C3—C7—N1	176.1 (4)
C1—C2—C3—C7	−93.8 (5)	C1—O1—C8—O2	32.4 (5)
O2—C2—C3—C4	−88.0 (4)	C1—O1—C8—C9	147.7 (4)
C1—C2—C3—C4	23.5 (4)	C1—O1—C8—C10	−86.7 (5)
C1—O4—C4—C5	164.9 (4)	C2—O2—C8—O1	−35.5 (5)
C1—O4—C4—C3	37.3 (5)	C2—O2—C8—C9	−151.4 (4)
O3—C3—C4—O4	−159.9 (4)	C2—O2—C8—C10	82.9 (5)
C7—C3—C4—O4	81.3 (4)	C5—O5—C11—O6	15.2 (6)
C2—C3—C4—O4	−36.8 (4)	C5—O5—C11—C12	133.6 (6)
O3—C3—C4—C5	81.4 (5)	C5—O5—C11—C13	−100.9 (5)
C7—C3—C4—C5	−37.4 (5)	C6—O6—C11—O5	10.1 (6)
C2—C3—C4—C5	−155.6 (4)	C6—O6—C11—C12	−106.5 (6)
C11—O5—C5—C6	−32.9 (5)	C6—O6—C11—C13	128.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3E···O6i	0.90 (8)	1.95 (8)	2.814 (5)	161 (7)
C1—H1A···O3ii	0.98	2.37	3.258 (4)	151.
C5—H5A···O1iii	0.98	2.50	3.320 (4)	141.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3E⋯O6i	0.90 (8)	1.95 (8)	2.814 (5)	161 (7)
C1—H1A⋯O3ii	0.98	2.37	3.258 (4)	151
C5—H5A⋯O1iii	0.98	2.50	3.320 (4)	141

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