(3R,3aS,6R,6aR)-3-(1-Nitro­eth­yl)perhydro­furo[3,2-b]furan-3,6-diol

Zhang, J.-Y.; Yang, J.

doi:10.1107/S1600536810022774

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1704

doi:10.1107/S1600536810022774

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(3R,3aS,6R,6aR)-3-(1-Nitroethyl)perhydrofuro[3,2-b]furan-3,6-diol

Jing-Yu Zhang ^a ^* and Jing Yang ^a

^aSchool of Pharmacy Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China
^*Correspondence e-mail: jyzhang2004@126.com

(Received 22 March 2010; accepted 14 June 2010; online 18 June 2010)

The molecule of the title compound, C₈H₁₃NO₆, a sucrose derivative, consists of two fused tetrahydrofuran rings having the cis arrangement at the ring junctions, giving a V-shaped molecule. An intramolecular O—H⋯O interaction occurs. Intermolecular 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_r = 219.19
Monoclinic, P 21
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.129
S = 0.98
932 reflections
137 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022774/jh2141sup1.cif

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

checkCIF report

Comment top

Sugar derivatives are an important class of compounds having a broad spectrum of applications in the chemical, biochemical, medicinal (Chang et al., 2001), and pharmaceutical fields,(Liu et al., 2004; Stutz et al., 1999) Here we report a structure of a novel Sugar derivatives. To develop new applications for sucrose and its derivatives, structural modifications of sucrose have been extensively investigated. As a contribution to the sucrose chemistry, we report here the crystal structure of the title compound.

Molecular structure of title compound is shown in Fig.1. Torsion angle C(6)—C(1)—C(2)—C(3) is -120.4. Intermolecular hydrogen bonds links molecules in crystal structure into three-dimensional structure.

Related literature top

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

Experimental top

Nitroethane and a catalytic amount of Et3N were added to a stirring solution of 1,4:3,6-dianhydrofructose in EtOH. The mixture was stirred at room temperature for 4 h, and evaporated under reduced pressure to dryness. The residue was recrystallized with EtOH to give title compound as a white crystal.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the compound, with atom labels and 50% probability displacement ellipsoids.
	Fig. 2. Crystal packing of the title compound, showing a three-dimensional structure, linked by hydrogen bonds(dashed lines).

(3R,3aS,6R,6aR)- 3-(1-Nitroethyl)perhydrofuro[3,2-b]furan-3,6-diol top

Crystal data top

C₈H₁₃NO₆	F(000) = 232
M_r = 219.19	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0843P)²] where P = (F_o² + 2F_c²)/3
932 reflections	(Δ/σ)_max < 0.001
137 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₈H₁₃NO₆	V = 472.5 (4) Å³
M_r = 219.19	Z = 2
Monoclinic, P21	Mo Kα radiation
a = 6.959 (4) Å	µ = 0.13 mm⁻¹
b = 5.525 (3) Å	T = 298 K
c = 12.384 (6) Å	0.42 × 0.23 × 0.14 mm
β = 97.077 (7)°

Data collection top

Siemens SMART CCD area-detector diffractometer	935 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	743 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.982	R_int = 0.059
2416 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.129	H-atom parameters constrained
S = 0.98	Δρ_max = 0.21 e Å⁻³
932 reflections	Δρ_min = −0.19 e Å⁻³
137 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z; (ii) −x+1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₈H₁₃NO₆
M_r	219.19
Crystal system, space group	Monoclinic, P21
Temperature (K)	298
a, b, c (Å)	6.959 (4), 5.525 (3), 12.384 (6)
β (°)	97.077 (7)
V (Å³)	472.5 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.42 × 0.23 × 0.14

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.946, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	2416, 935, 743
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.129, 0.98
No. of reflections	932
No. of parameters	137
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19
Absolute structure parameter	1 (3)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.82	2.06	2.785 (5)	147.0
O4—H4···O3ⁱⁱ	0.82	2.05	2.777 (4)	147.2
O4—H4···O1	0.82	2.23	2.655 (4)	112.7

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z+1.

Acknowledgements

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 20572103).

References

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