(3R,3aS,6R,6aR)-3-(1-Nitro-eth-yl)perhydro-furo[3,2-b]furan-3,6-diol.

The mol-ecule of the title compound, C(8)H(13)NO(6), a sucrose derivative, consists of two fused tetra-hydro-furan rings having the cis arrangement at the ring junctions, giving a V-shaped mol-ecule. An intra-molecular O-H⋯O inter-action occurs. Inter-molecular O-H⋯O hydrogen bonds help to stabilize the crystal structure.

Related literature

For applications of sucrose and its derivatives, see: Chang et al. (2001 ▶); Liu et al. (2004 ▶); Stutz et al. (1999 ▶).

Experimental

Crystal data

C8H13NO6

M = 219.19

Monoclinic,

a = 6.959 (4) Å

b = 5.525 (3) Å

c = 12.384 (6) Å

β = 97.077 (7)°

V = 472.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 298 K

0.42 × 0.23 × 0.14 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.946, T max = 0.982

2416 measured reflections

935 independent reflections

743 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.129

S = 0.98

932 reflections

137 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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/S1600536810022774/jh2141sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022774/jh2141Isup2.hkl

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

C8H13NO6	F(000) = 232
Mr = 219.19	Dx = 1.541 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 6.959 (4) Å	Cell parameters from 895 reflections
b = 5.525 (3) Å	θ = 3.0–22.5°
c = 12.384 (6) Å	µ = 0.13 mm−1
β = 97.077 (7)°	T = 298 K
V = 472.5 (4) Å3	Colorless, needlelike
Z = 2	0.42 × 0.23 × 0.14 mm

Siemens SMART CCD area-detector diffractometer	935 independent reflections
Radiation source: fine-focus sealed tube	743 reflections with I > 2σ(I)
graphite	Rint = 0.059
phi and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→8
Tmin = 0.946, Tmax = 0.982	k = −6→6
2416 measured reflections	l = −14→14

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0843P)2] where P = (Fo2 + 2Fc2)/3
932 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

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
N1	0.9397 (6)	0.4876 (9)	0.8645 (3)	0.0565 (11)
O1	0.3548 (4)	0.4642 (5)	0.61605 (19)	0.0468 (7)
O2	0.5198 (4)	−0.0131 (5)	0.7607 (2)	0.0485 (7)
O3	0.3353 (5)	−0.0495 (6)	0.55654 (18)	0.0586 (9)
H3	0.3836	−0.1713	0.5865	0.088*
O4	0.7338 (4)	0.5239 (6)	0.6667 (2)	0.0475 (8)
H4	0.6696	0.5192	0.6066	0.071*
O5	1.0171 (6)	0.6770 (9)	0.8438 (3)	0.0869 (13)
O6	1.0297 (6)	0.3057 (9)	0.8937 (3)	0.0867 (12)
C1	0.4230 (5)	0.3930 (7)	0.7261 (3)	0.0402 (10)
H1	0.3753	0.5017	0.7795	0.048*
C2	0.3545 (6)	0.1339 (7)	0.7386 (3)	0.0419 (9)
H2	0.2752	0.1239	0.7986	0.050*
C3	0.2290 (7)	0.0763 (8)	0.6291 (3)	0.0469 (10)
H3A	0.1108	−0.0111	0.6407	0.056*
C4	0.1837 (6)	0.3261 (9)	0.5835 (3)	0.0512 (11)
H4A	0.1558	0.3209	0.5049	0.061*
H4B	0.0732	0.3949	0.6133	0.061*
C5	0.6784 (6)	0.1117 (8)	0.7223 (4)	0.0463 (10)
H5A	0.6822	0.0785	0.6456	0.056*
H5B	0.8001	0.0608	0.7625	0.056*
C6	0.6445 (5)	0.3804 (7)	0.7401 (3)	0.0390 (9)
C7	0.7219 (5)	0.4776 (9)	0.8547 (3)	0.0454 (10)
H7	0.6749	0.6440	0.8596	0.055*
C8	0.6571 (6)	0.3377 (10)	0.9479 (3)	0.0553 (12)
H8A	0.7002	0.1730	0.9450	0.083*
H8B	0.5184	0.3413	0.9429	0.083*
H8C	0.7115	0.4094	1.0154	0.083*

	U11	U22	U33	U12	U13	U23
N1	0.056 (2)	0.072 (3)	0.0384 (18)	0.008 (2)	−0.0049 (16)	−0.008 (2)
O1	0.0563 (16)	0.0408 (16)	0.0409 (14)	0.0072 (14)	−0.0031 (12)	0.0095 (13)
O2	0.0592 (17)	0.0359 (16)	0.0496 (15)	0.0079 (14)	0.0034 (13)	0.0026 (14)
O3	0.099 (2)	0.0404 (17)	0.0355 (14)	0.0131 (17)	0.0040 (15)	0.0019 (14)
O4	0.0544 (16)	0.0548 (19)	0.0330 (13)	−0.0059 (15)	0.0037 (12)	−0.0004 (13)
O5	0.072 (2)	0.102 (3)	0.081 (3)	−0.026 (3)	−0.012 (2)	0.000 (2)
O6	0.069 (2)	0.099 (3)	0.090 (3)	0.029 (2)	0.001 (2)	−0.007 (3)
C1	0.051 (2)	0.039 (2)	0.0301 (18)	0.010 (2)	0.0039 (16)	0.0002 (16)
C2	0.047 (2)	0.043 (2)	0.0353 (19)	0.004 (2)	0.0038 (16)	0.0008 (18)
C3	0.057 (2)	0.042 (2)	0.041 (2)	−0.003 (2)	0.0034 (18)	0.0019 (18)
C4	0.052 (3)	0.054 (3)	0.044 (2)	0.003 (2)	−0.0067 (18)	−0.001 (2)
C5	0.051 (2)	0.042 (2)	0.046 (2)	0.007 (2)	0.0061 (18)	−0.0064 (19)
C6	0.050 (2)	0.038 (2)	0.0289 (19)	−0.0013 (18)	0.0054 (16)	−0.0012 (15)
C7	0.052 (2)	0.048 (2)	0.0360 (18)	0.008 (2)	0.0031 (16)	−0.002 (2)
C8	0.070 (3)	0.064 (3)	0.033 (2)	0.006 (3)	0.0090 (18)	0.0003 (19)

N1—O6	1.215 (6)	C2—H2	0.9800
N1—O5	1.219 (6)	C3—C4	1.509 (6)
N1—C7	1.506 (5)	C3—H3A	0.9800
O1—C4	1.430 (5)	C4—H4A	0.9700
O1—C1	1.442 (4)	C4—H4B	0.9700
O2—C2	1.408 (5)	C5—C6	1.523 (6)
O2—C5	1.431 (5)	C5—H5A	0.9700
O3—C3	1.415 (5)	C5—H5B	0.9700
O3—H3	0.8200	C6—C7	1.550 (5)
O4—C6	1.407 (5)	C7—C8	1.504 (6)
O4—H4	0.8200	C7—H7	0.9800
C1—C2	1.523 (6)	C8—H8A	0.9600
C1—C6	1.531 (5)	C8—H8B	0.9600
C1—H1	0.9800	C8—H8C	0.9600
C2—C3	1.552 (5)
O6—N1—O5	123.2 (4)	O1—C4—H4B	110.8
O6—N1—C7	118.1 (5)	C3—C4—H4B	110.8
O5—N1—C7	118.7 (4)	H4A—C4—H4B	108.9
C4—O1—C1	106.6 (3)	O2—C5—C6	106.4 (3)
C2—O2—C5	107.6 (3)	O2—C5—H5A	110.5
C3—O3—H3	109.5	C6—C5—H5A	110.5
C6—O4—H4	109.5	O2—C5—H5B	110.5
O1—C1—C2	106.4 (3)	C6—C5—H5B	110.5
O1—C1—C6	109.2 (3)	H5A—C5—H5B	108.6
C2—C1—C6	105.6 (3)	O4—C6—C5	111.5 (3)
O1—C1—H1	111.8	O4—C6—C1	114.8 (3)
C2—C1—H1	111.8	C5—C6—C1	101.5 (3)
C6—C1—H1	111.8	O4—C6—C7	105.3 (3)
O2—C2—C1	107.7 (3)	C5—C6—C7	115.3 (3)
O2—C2—C3	114.2 (3)	C1—C6—C7	108.6 (3)
C1—C2—C3	104.7 (3)	C8—C7—N1	110.5 (3)
O2—C2—H2	110.0	C8—C7—C6	114.9 (4)
C1—C2—H2	110.0	N1—C7—C6	108.6 (3)
C3—C2—H2	110.0	C8—C7—H7	107.5
O3—C3—C4	108.2 (3)	N1—C7—H7	107.5
O3—C3—C2	111.9 (3)	C6—C7—H7	107.5
C4—C3—C2	102.0 (3)	C7—C8—H8A	109.5
O3—C3—H3A	111.4	C7—C8—H8B	109.5
C4—C3—H3A	111.4	H8A—C8—H8B	109.5
C2—C3—H3A	111.4	C7—C8—H8C	109.5
O1—C4—C3	104.7 (3)	H8A—C8—H8C	109.5
O1—C4—H4A	110.8	H8B—C8—H8C	109.5
C3—C4—H4A	110.8
C4—O1—C1—C2	27.7 (4)	O2—C5—C6—C7	85.8 (4)
C4—O1—C1—C6	141.2 (3)	O1—C1—C6—O4	24.1 (4)
C5—O2—C2—C1	−22.0 (4)	C2—C1—C6—O4	138.1 (3)
C5—O2—C2—C3	93.8 (4)	O1—C1—C6—C5	−96.3 (3)
O1—C1—C2—O2	117.5 (3)	C2—C1—C6—C5	17.7 (3)
C6—C1—C2—O2	1.5 (4)	O1—C1—C6—C7	141.7 (3)
O1—C1—C2—C3	−4.4 (4)	C2—C1—C6—C7	−104.3 (4)
C6—C1—C2—C3	−120.4 (3)	O6—N1—C7—C8	40.8 (5)
O2—C2—C3—O3	−20.6 (5)	O5—N1—C7—C8	−138.7 (4)
C1—C2—C3—O3	96.9 (4)	O6—N1—C7—C6	−86.2 (4)
O2—C2—C3—C4	−136.1 (4)	O5—N1—C7—C6	94.4 (5)
C1—C2—C3—C4	−18.6 (4)	O4—C6—C7—C8	−175.5 (3)
C1—O1—C4—C3	−40.5 (4)	C5—C6—C7—C8	−52.1 (5)
O3—C3—C4—O1	−82.4 (4)	C1—C6—C7—C8	61.0 (5)
C2—C3—C4—O1	35.8 (4)	O4—C6—C7—N1	−51.2 (4)
C2—O2—C5—C6	34.2 (4)	C5—C6—C7—N1	72.2 (4)
O2—C5—C6—O4	−154.1 (3)	C1—C6—C7—N1	−174.7 (3)
O2—C5—C6—C1	−31.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1i	0.82	2.06	2.785 (5)	147
O4—H4···O3ii	0.82	2.05	2.777 (4)	147
O4—H4···O1	0.82	2.23	2.655 (4)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1i	0.82	2.06	2.785 (5)	147
O4—H4⋯O3ii	0.82	2.05	2.777 (4)	147
O4—H4⋯O1	0.82	2.23	2.655 (4)	113

Symmetry codes: (i) ; (ii) .