1,2;5,6-Di-O-isopropyl­idene-3-C-nitro­methyl-α-d-allofuran­ose

Zhang, Q.; Ke, Y.; Cheng, W.; Li, P.; Liu, H.

doi:10.1107/S1600536811017314

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1402

doi:10.1107/S1600536811017314

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1,2;5,6-Di-O-isopropylidene-3-C-nitromethyl-α-D-allofuranose

Qiurong Zhang,^a Yu Ke,^a Weiyan Cheng,^a Pengyun Li ^a and Hongmin Liu ^a ^*

^aNew Drug Reseach & Development Center, Zhengzhou University, Zhengzhou 450001, People's Republic of China
^*Correspondence e-mail: zqr409@126.com

(Received 4 May 2011; accepted 7 May 2011; online 14 May 2011)

The molecule of the title compound, C₁₃H₂₁NO₈, consists of two methylenedioxy rings and one tetrahydrofuran ring. In the crystal, intermolecular O—H⋯O hydrogen bonds link the molecules into helical chains running along the 6₁ screw axis. Weak intermolecular C—H⋯O hydrogen bonds help to stabilize the crystal packing. Voids of 245 Å³ 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_r = 319.31
Hexagonal, P 6₁
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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.164
S = 1.08
1612 reflections
205 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) $[x-y, x, z+{\script{1\over 6}}]$ ; (ii) $[x-y+1, x+1, z+{\script{1\over 6}}]$ ; (iii) $[-x+y, -x+1, z-{\script{1\over 3}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Azasugars were recently used as novel glycosyls to synthesize novel N-nucleosides (Loiseleur et al., 2007; Rahman et al., 2008). Herewith we report the synthesis and crystal structure of the title compound (I) prepared in enantiomerically pure form from 1,2;5,6-di-O-isopropylidene-3-carbonyl-α-D-glucofuranose (Saito et al., 2002) at room tempeature, whose raw material was D-glucose.

The molecule of (I) consists of two methylenedioxy rings and one tetrahydrofuran ring (Fig. 1). In (I), the tetrahydrofuran ring fuses with one methylenedioxy ring, having the cis arrangement at the ring junctions and giving a V-shaped molecule. The angles O1—C8—O2, O5—C11—O6, C9—C8—C10 and C12—C11—C13 around the two isopropylidenes are 104.1 (4), 105.5 (4), 113.9 (5) and 114.2 (6)°, respectively.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into helical chains running along screw axis 6₁, and weak intermolecular C—H···O hydrogen bonds (Table 1) help to stabilize the crystal packing.

Related literature top

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 top

All reagents and solvents were used as obtained without further purification. 1,2;5,6-di-O-isopropylidene-3-C-(nitromethyl)- α-D-allofuranose was synthesized from 1,2;5,6-di-O-isopropylidene-3-carbonyl-α-D-glucofuranose as described previously by Saito et al. (2002), whose starting material was D-glucose. To a solution of 1,2;5,6-di-O-isopropylidene-3-carbonyl -α-D-Glucofuranose (7.0 g, 27 mmol) in tetrahydrofuran (50 ml) was added CH₃NO₂ (10.5 ml) and potassium fluoride (3.0 g).The mixture was stirred at room temperature for 6 h. The reaction mixture was then concentrated in vacuo and extracted with water and EtOAc, dried (Na₂SO₄), and evaporated. The residue was recrystalied in CH₃OH to yield the title compound. Crystals suitable for X-ray analysis were grown by slow evaporation from methanol at room temperature for two weeks. R_f = 0.7 (CHCl₃/EtOAc, 7:3); mp: 110–111°C, [α]²⁰_D = +96° (c, 1.0, CH₃OH); ¹H NMR (400 MHz, CDCl₃) σ: 5.85(1H, d, J = 3.6 Hz), 4.97 (1H, d, J = 12 Hz), 4.89 (1H, d, J = 3.6 Hz), 4.49 (1H, d, J = 12 Hz), 4.13 (1H, m), 4.01(1H,m), 3.95 (1H, m), 3.89 (1H, d, J = 8.8), 3.27 (1H, s), 1.61 (3H, s), 1.47 (3H, s), 1.39 (3H, s), 1.36 (3H, s); ¹³C NMR (100 MHz, CDCl₃) σ: 113.3, 110.4, 103.7, 81.7, 79.8, 78.5, 77.6, 72.9, 67.9, 26.6, 26.5, 26.5, 25.0.

Computing details top

Data collection: R-AXIS-IV Software (Rigaku, 1997); cell refinement: R-AXIS-IV Software (Rigaku, 1997); data reduction: R-AXIS-IV Software (Rigaku, 1997); 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 (Molecular Structure Corporation, 1992).

Figures top

	Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids. H atoms omitted for clarity.
	Fig. 2. Packing diagram.

1,2;5,6-Di-O-isopropylidene-3-C-nitromethyl-α-D-allofuranose top

Crystal data top

C₁₃H₂₁NO₈	D_x = 1.270 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0962P)² + 1.0744P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
1612 reflections	Δρ_max = 0.43 e Å⁻³
205 parameters	Δρ_min = −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)

Crystal data top

C₁₃H₂₁NO₈	Z = 6
M_r = 319.31	Mo Kα radiation
Hexagonal, P6₁	µ = 0.11 mm⁻¹
a = 13.2581 (19) Å	T = 291 K
c = 16.462 (3) Å	0.24 × 0.20 × 0.20 mm
V = 2506.0 (7) Å³

Data collection top

Rigaku R-AXIS-IV diffractometer	1612 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1534 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.979	R_int = 0.047
8380 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	1 restraint
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.43 e Å⁻³
1612 reflections	Δρ_min = −0.26 e Å⁻³
205 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−y, x, z+1/6; (ii) x−y+1, x+1, z+1/6; (iii) −x+y, −x+1, z−1/3.

Experimental details

Crystal data
Chemical formula	C₁₃H₂₁NO₈
M_r	319.31
Crystal system, space group	Hexagonal, P6₁
Temperature (K)	291
a, c (Å)	13.2581 (19), 16.462 (3)
V (Å³)	2506.0 (7)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.24 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS-IV diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.975, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	8380, 1612, 1534
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.164, 1.08
No. of reflections	1612
No. of parameters	205
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.26

Computer programs: R-AXIS-IV Software (Rigaku, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), TEXSAN (Molecular Structure Corporation, 1992).

Hydrogen-bond geometry (Å, º) top

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)	150.9
C5—H5A···O1ⁱⁱⁱ	0.98	2.50	3.320 (4)	140.9

Symmetry codes: (i) x−y, x, z+1/6; (ii) x−y+1, x+1, z+1/6; (iii) −x+y, −x+1, z−1/3.

Acknowledgements

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

References

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