N-Benzyl-6-de­oxy-3,6-imino­methyl­ene-1,2,3,5-O-tetra­acetyl-α-d-1(S)-epiallo­furan­ose

Zhang, Q.; Wu, C.; Li, P.; Cheng, W.; Liu, H.

doi:10.1107/S1600536811019702

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1545

doi:10.1107/S1600536811019702

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N-Benzyl-6-deoxy-3,6-iminomethylene-1,2,3,5-O-tetraacetyl-α-D-1(S)-epiallofuranose

Qiurong Zhang,^a Chunli Wu,^a Pengyun Li,^a Weiyan Cheng ^a and Hongmin Liu ^a ^*

^aNew Drug Reseach & Development Center, Zhengzhou Univresity, Zhengzhou 450001, People's Republic of China
^*Correspondence e-mail: zqr409@163.com

(Received 6 May 2011; accepted 24 May 2011; online 28 May 2011)

The molecule of the title compound, C₂₂H₂₇NO₉, an azasugar derivative, consists of one benzene ring and two fused rings, which have the cis arrangement at the ring junctions, and gives a V-shaped geometry. The interplanar angle between the five- and six-membered rings is 65.69 (11)°. The crystal structure is stablized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the one-pot reaction used to obtain the title compound, see: Saito et al. (2002 ); Deshpandea et al. (2004 ). For the activity of azasugars, see: Compain et al. (2001 , 2003 ). For their powerful inhibitory aptitude towards carbohydrate-processing enzymes, see: Guaragna et al. (2009 ).

Experimental

Crystal data

C₂₂H₂₇NO₉
M_r = 449.45
Monoclinic, P 2₁
a = 8.1768 (16) Å
b = 9.0613 (18) Å
c = 15.591 (3) Å
β = 94.56 (3)°
V = 1151.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 291 K
0.20 × 0.18 × 0.16 mm

Data collection

Rigaku R-AXIS-IV diffractometer
Absorption correction: multi-scan (SADABS: Sheldrick, 1996 ) T_min = 0.980, T_max = 0.984
4341 measured reflections
2503 independent reflections
2173 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.107
S = 1.09
2503 reflections
290 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯O6ⁱ	0.96	2.33	3.161 (5)	144
Symmetry code: (i) x-1, y, z.

Data collection: R-AXIS II Software (Rigaku, 1997 ); cell refinement: R-AXIS II Software; data reduction: R-AXIS II Software; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019702/zk2010sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019702/zk2010Isup2.hkl

checkCIF report

Comment top

Owing to their powerful inhibitory aptitude towards carbohydrate processing enzymes, azasugars undoubtedly represent one of the most attractive classes of carbohydrate mimetics (Guaragna et al., 2009). As a contribution to the azasugars chemistry, we report here the crystal structure of the title compound, which was obtained under one-pot reaction (Sachin et al., 2004 and Saito et al., 2002) of N-benzyl-6-deoxy- 3,6-imino-methylene-1,2-O-isopropylidene-α-D-allofuranose.

In the crystal structure of the title compound (I) (Fig. 1), there are two fused rings (tetrahydrofuran ring and piperidine ring) having the cis arrangement at the ring junctions, giving a V-shaped molecule. The interplanar angle between the five and six membered rings is 65.69 (11)°. The torsion angles O1—C1—C2—C3, O1—C1—C2—O2 and C4—O4—C1—O1 around the carbon of hemiacetal group(C1) are 109.0 (2), -136.5 (2) and -137.1 (2)° respectively, which can confirm the hemiacetal group is β configuration. The molecules are linked into a framework by means of weak C—H···O hydrogen bonds (Table 1), one of whcih occurs between CH₃ of C5-acetoxy moiety and O atoms of carbonyl of C1-acetoxy moiety, and three of which occur among CH and CH₂groups of five and six membered rings and O atoms of carbonyl of three acetoxy moieties (Fig. 2).

Related literature top

For the one-pot reaction used to obtain the title compound, see: Saito et al. (2002); Deshpandea et al. (2004). For the activity of azasugars, see: Compain et al. (2001, 2003). For their powerful inhibitory aptitude towards carbohydrate-processing enzymes, see: Guaragna et al. (2009).

Experimental top

N-benzyl-6-deoxy-3,6-imino-methylene- 1,2-O-isopropylidene-α-D-allofuranose (2.0 g, 6.2 mmol) was dissolved in 85% acetic acid (10 ml). A solution of 15% hydrochoric acid was added to this mixture. The resulting mixture was stirred for about 6 h at ambient temperature. After the material was consumed, the reaction mixture was evaporated under reduced pressure to dryness to yield yellow solid, which was directly used without purification. Acetic anhydride (5 ml) was added to the yellow solid in dry pyridine (5 ml). The mixture was stirred for about 5 h at ambient temperature. The reaction mixture was adjusted to neutral with saturated NaHCO₃ under ice bath and filtered. The filtrate was extracted with EtOAc, dried (Na₂SO₄), and evaporated to obtained colorless oily. The oily was recrystallized from methanol to give the title compound as a white crystal. Crystals suitable for X-ray analysis were in two weeks by slow evaporation of methanol solution of the title compound at room temperature. ¹H NMR (400 MHz, CDCl₃) σ: 7.25–7.33 (5 H, m), 6.03 (1 H, s), 5.32 (1 H, s), 5.21 (1 H, m), 4.40 (1 H, d, J = 3.2 Hz), 3.62 (2 H, dd), 3.34 (1 H, d, J= 13.6 Hz), 2.81 (1 H, m), 2.54 (1 H, d, J = 13.6 Hz), 2.42 (1 H, m), 2.09 (3 H, s), 2.09(3 H, s), 2.08 (3 H, s), 2.07 (3 H, s), 2.04 (3 H, s); ¹³C NMR (100 MHz, CDCl₃) σ: 170.2, 169.3, 168.9, 168.6, 137.0, 128.7, 128.3, 127.4, 99.3, 80.2, 77.4, 76.5, 68.1, 61.4, 51.4, 49.9, 21.1, 21.1, 21.0, 20.5.

Computing details top

Data collection: R-AXIS II Software (Rigaku, 1997); cell refinement: R-AXIS II Software (Rigaku, 1997); data reduction: R-AXIS II Software (Rigaku, 1997); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Packing of the molecules crystal structure of title compound, the molecules are connected by the C—H···O hydrogen bonds.

N-Benzyl-6-deoxy-3,6-iminomethylene-1,2,3,5-O-tetraacetyl- α-D-1(S)-epiallofuranose top

Crystal data top

C₂₂H₂₇NO₉	F(000) = 476
M_r = 449.45	D_x = 1.296 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 399 reflections
a = 8.1768 (16) Å	θ = 2–25.1°
b = 9.0613 (18) Å	µ = 0.10 mm⁻¹
c = 15.591 (3) Å	T = 291 K
β = 94.56 (3)°	PRISMATIC, colorless
V = 1151.5 (4) Å³	0.20 × 0.18 × 0.16 mm
Z = 2

Data collection top

Rigaku R-AXIS-IV diffractometer	2503 independent reflections
Radiation source: fine-focus sealed tube	2173 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 0 pixels mm^-1	θ_max = 26.5°, θ_min = 1.3°
Oscillation frames scans	h = 0→10
Absorption correction: multi-scan (SADABS: Sheldrick, 1996)	k = −11→11
T_min = 0.980, T_max = 0.984	l = −19→19
4341 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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0659P)²] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2503 reflections	Δρ_max = 0.15 e Å⁻³
290 parameters	Δρ_min = −0.13 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (5)

Crystal data top

C₂₂H₂₇NO₉	V = 1151.5 (4) Å³
M_r = 449.45	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.1768 (16) Å	µ = 0.10 mm⁻¹
b = 9.0613 (18) Å	T = 291 K
c = 15.591 (3) Å	0.20 × 0.18 × 0.16 mm
β = 94.56 (3)°

Data collection top

Rigaku R-AXIS-IV diffractometer	2503 independent reflections
Absorption correction: multi-scan (SADABS: Sheldrick, 1996)	2173 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.984	R_int = 0.033
4341 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.107	H-atom parameters constrained
S = 1.09	Δρ_max = 0.15 e Å⁻³
2503 reflections	Δρ_min = −0.13 e Å⁻³
290 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	0.1159 (3)	0.9181 (3)	0.34251 (14)	0.0450 (6)
O1	0.5766 (2)	1.1411 (2)	0.25616 (13)	0.0515 (5)
O2	0.5092 (2)	0.8192 (2)	0.13055 (12)	0.0471 (5)
O3	0.2300 (2)	0.7356 (2)	0.19908 (12)	0.0439 (5)
O4	0.3209 (2)	1.1154 (2)	0.18522 (13)	0.0461 (5)
O5	−0.0199 (2)	1.1524 (2)	0.15811 (13)	0.0489 (5)
O6	0.5922 (3)	1.3316 (3)	0.16484 (19)	0.0771 (7)
O7	0.7528 (3)	0.7358 (3)	0.18663 (16)	0.0700 (7)
O8	0.4156 (3)	0.5948 (3)	0.27378 (14)	0.0589 (6)
O9	−0.1360 (4)	1.0104 (3)	0.05304 (17)	0.0886 (9)
C1	0.4843 (3)	1.0630 (3)	0.18939 (19)	0.0438 (6)
H1A	0.5311	1.0805	0.1343	0.053*
C2	0.4826 (3)	0.8971 (3)	0.20843 (16)	0.0393 (6)
H2A	0.5621	0.8696	0.2561	0.047*
C3	0.3042 (3)	0.8717 (3)	0.22978 (17)	0.0376 (6)
C4	0.2149 (3)	0.9901 (3)	0.17496 (18)	0.0391 (6)
H4A	0.2062	0.9591	0.1146	0.047*
C5	0.0450 (3)	1.0225 (3)	0.20286 (18)	0.0428 (6)
H5A	−0.0268	0.9385	0.1872	0.051*
C6	0.0463 (3)	1.0483 (4)	0.29899 (19)	0.0486 (7)
H6A	0.1118	1.1345	0.3153	0.058*
H6B	−0.0645	1.0647	0.3149	0.058*
C7	0.2889 (3)	0.8982 (3)	0.32508 (16)	0.0429 (6)
H7A	0.3346	0.8149	0.3579	0.052*
H7B	0.3509	0.9855	0.3433	0.052*
C8	0.6243 (3)	1.2802 (4)	0.2351 (3)	0.0569 (8)
C9	0.7193 (4)	1.3524 (5)	0.3088 (3)	0.0813 (12)
H9A	0.7512	1.4497	0.2923	0.122*
H9B	0.8155	1.2951	0.3251	0.122*
H9C	0.6525	1.3590	0.3566	0.122*
C10	0.6505 (3)	0.7422 (3)	0.1276 (2)	0.0496 (7)
C11	0.6557 (5)	0.6680 (5)	0.0432 (2)	0.0733 (10)
H11A	0.7565	0.6139	0.0420	0.110*
H11B	0.6494	0.7407	−0.0018	0.110*
H11C	0.5646	0.6013	0.0345	0.110*
C12	0.2937 (3)	0.6055 (3)	0.2257 (2)	0.0473 (7)
C13	0.1927 (5)	0.4817 (4)	0.1878 (3)	0.0770 (11)
H13A	0.2399	0.3895	0.2075	0.115*
H13B	0.1899	0.4862	0.1262	0.115*
H13C	0.0831	0.4895	0.2054	0.115*
C14	−0.1022 (4)	1.1307 (4)	0.08049 (19)	0.0501 (7)
C15	−0.1374 (4)	1.2725 (4)	0.0348 (2)	0.0664 (10)
H15A	−0.1958	1.2534	−0.0199	0.100*
H15B	−0.0361	1.3219	0.0262	0.100*
H15C	−0.2031	1.3339	0.0687	0.100*
C16	0.0969 (4)	0.9206 (5)	0.43531 (19)	0.0587 (8)
H16A	0.1255	1.0180	0.4576	0.070*
H16B	0.1727	0.8504	0.4637	0.070*
C17	−0.0747 (3)	0.8835 (4)	0.45673 (18)	0.0511 (8)
C18	−0.1365 (5)	0.9410 (6)	0.5301 (2)	0.0842 (14)
H18A	−0.0748	1.0086	0.5639	0.101*
C19	−0.2898 (5)	0.8983 (8)	0.5533 (3)	0.107 (2)
H19A	−0.3307	0.9381	0.6023	0.128*
C20	−0.3806 (4)	0.7987 (7)	0.5048 (3)	0.0886 (15)
H20A	−0.4820	0.7684	0.5215	0.106*
C21	−0.3232 (4)	0.7438 (5)	0.4322 (2)	0.0690 (10)
H21A	−0.3867	0.6778	0.3981	0.083*
C22	−0.1714 (4)	0.7852 (4)	0.4087 (2)	0.0551 (8)
H22A	−0.1332	0.7456	0.3590	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0465 (12)	0.0503 (14)	0.0377 (12)	0.0078 (11)	0.0004 (9)	0.0007 (11)
O1	0.0520 (11)	0.0460 (12)	0.0553 (12)	−0.0058 (10)	−0.0042 (8)	−0.0094 (10)
O2	0.0529 (10)	0.0469 (12)	0.0407 (10)	0.0098 (10)	−0.0010 (8)	−0.0082 (9)
O3	0.0525 (10)	0.0281 (9)	0.0493 (11)	0.0011 (8)	−0.0072 (8)	−0.0006 (9)
O4	0.0463 (10)	0.0301 (10)	0.0609 (12)	−0.0010 (8)	−0.0033 (8)	0.0031 (9)
O5	0.0541 (11)	0.0351 (10)	0.0551 (12)	0.0073 (9)	−0.0101 (9)	0.0059 (9)
O6	0.0976 (18)	0.0516 (15)	0.0848 (19)	−0.0140 (14)	0.0235 (14)	−0.0001 (15)
O7	0.0537 (11)	0.0827 (18)	0.0724 (15)	0.0187 (13)	−0.0030 (11)	−0.0070 (14)
O8	0.0694 (13)	0.0403 (12)	0.0643 (14)	0.0104 (10)	−0.0114 (11)	0.0051 (10)
O9	0.132 (2)	0.0629 (19)	0.0632 (16)	−0.0026 (16)	−0.0376 (15)	0.0019 (14)
C1	0.0451 (14)	0.0417 (16)	0.0437 (15)	−0.0028 (12)	−0.0019 (11)	−0.0016 (12)
C2	0.0458 (13)	0.0380 (15)	0.0333 (13)	0.0064 (11)	−0.0017 (10)	−0.0032 (11)
C3	0.0440 (13)	0.0284 (13)	0.0389 (14)	0.0011 (11)	−0.0059 (10)	−0.0008 (11)
C4	0.0478 (14)	0.0299 (14)	0.0382 (14)	−0.0005 (11)	−0.0048 (11)	−0.0011 (11)
C5	0.0453 (14)	0.0304 (14)	0.0505 (16)	0.0041 (12)	−0.0097 (12)	0.0031 (12)
C6	0.0478 (14)	0.0480 (18)	0.0493 (17)	0.0100 (13)	−0.0006 (12)	−0.0023 (14)
C7	0.0462 (13)	0.0450 (16)	0.0362 (13)	0.0053 (12)	−0.0052 (10)	0.0024 (13)
C8	0.0457 (15)	0.0437 (18)	0.082 (2)	−0.0031 (13)	0.0118 (15)	−0.0152 (17)
C9	0.0606 (19)	0.062 (2)	0.119 (3)	−0.0016 (18)	−0.0048 (19)	−0.040 (2)
C10	0.0489 (14)	0.0401 (15)	0.0604 (19)	0.0019 (13)	0.0086 (13)	0.0001 (15)
C11	0.084 (2)	0.070 (2)	0.068 (2)	0.012 (2)	0.0200 (17)	−0.020 (2)
C12	0.0549 (16)	0.0341 (15)	0.0523 (17)	0.0037 (13)	0.0014 (13)	0.0062 (13)
C13	0.086 (2)	0.042 (2)	0.099 (3)	−0.0069 (18)	−0.015 (2)	0.003 (2)
C14	0.0511 (15)	0.054 (2)	0.0439 (16)	0.0042 (14)	−0.0049 (12)	0.0069 (15)
C15	0.0665 (18)	0.068 (2)	0.064 (2)	0.0137 (17)	−0.0023 (15)	0.0268 (18)
C16	0.0624 (18)	0.074 (2)	0.0394 (16)	0.0000 (17)	0.0001 (13)	−0.0014 (16)
C17	0.0490 (15)	0.064 (2)	0.0404 (15)	0.0121 (15)	0.0019 (12)	0.0024 (15)
C18	0.074 (2)	0.117 (4)	0.061 (2)	0.002 (2)	0.0043 (18)	−0.034 (2)
C19	0.072 (2)	0.188 (6)	0.064 (2)	0.006 (3)	0.0209 (19)	−0.044 (3)
C20	0.0533 (17)	0.147 (5)	0.066 (2)	0.004 (3)	0.0058 (16)	−0.003 (3)
C21	0.0557 (17)	0.090 (3)	0.060 (2)	0.0025 (19)	−0.0044 (14)	0.001 (2)
C22	0.0602 (16)	0.060 (2)	0.0438 (16)	0.0102 (16)	−0.0012 (13)	−0.0006 (14)

Geometric parameters (Å, º) top

N1—C6	1.454 (4)	C8—C9	1.487 (5)
N1—C16	1.468 (4)	C9—H9A	0.9600
N1—C7	1.472 (3)	C9—H9B	0.9600
O1—C8	1.368 (4)	C9—H9C	0.9600
O1—C1	1.424 (3)	C10—C11	1.483 (5)
O2—C10	1.353 (3)	C11—H11A	0.9600
O2—C2	1.436 (3)	C11—H11B	0.9600
O3—C12	1.341 (3)	C11—H11C	0.9600
O3—C3	1.440 (3)	C12—C13	1.487 (5)
O4—C1	1.415 (3)	C13—H13A	0.9600
O4—C4	1.429 (3)	C13—H13B	0.9600
O5—C14	1.352 (4)	C13—H13C	0.9600
O5—C5	1.447 (3)	C14—C15	1.486 (5)
O6—C8	1.200 (4)	C15—H15A	0.9600
O7—C10	1.194 (4)	C15—H15B	0.9600
O8—C12	1.203 (3)	C15—H15C	0.9600
O9—C14	1.195 (4)	C16—C17	1.506 (4)
C1—C2	1.532 (4)	C16—H16A	0.9700
C1—H1A	0.9800	C16—H16B	0.9700
C2—C3	1.539 (4)	C17—C22	1.374 (4)
C2—H2A	0.9800	C17—C18	1.389 (5)
C3—C7	1.520 (4)	C18—C19	1.387 (6)
C3—C4	1.522 (4)	C18—H18A	0.9300
C4—C5	1.517 (4)	C19—C20	1.360 (7)
C4—H4A	0.9800	C19—H19A	0.9300
C5—C6	1.516 (4)	C20—C21	1.355 (6)
C5—H5A	0.9800	C20—H20A	0.9300
C6—H6A	0.9700	C21—C22	1.374 (5)
C6—H6B	0.9700	C21—H21A	0.9300
C7—H7A	0.9700	C22—H22A	0.9300
C7—H7B	0.9700

C6—N1—C16	112.3 (2)	H9A—C9—H9B	109.5
C6—N1—C7	111.0 (2)	C8—C9—H9C	109.5
C16—N1—C7	111.2 (2)	H9A—C9—H9C	109.5
C8—O1—C1	115.3 (3)	H9B—C9—H9C	109.5
C10—O2—C2	118.0 (2)	O7—C10—O2	123.1 (3)
C12—O3—C3	120.49 (18)	O7—C10—C11	126.4 (3)
C1—O4—C4	107.5 (2)	O2—C10—C11	110.4 (3)
C14—O5—C5	116.8 (2)	C10—C11—H11A	109.5
O4—C1—O1	108.1 (2)	C10—C11—H11B	109.5
O4—C1—C2	108.4 (2)	H11A—C11—H11B	109.5
O1—C1—C2	111.0 (2)	C10—C11—H11C	109.5
O4—C1—H1A	109.8	H11A—C11—H11C	109.5
O1—C1—H1A	109.8	H11B—C11—H11C	109.5
C2—C1—H1A	109.8	O8—C12—O3	123.1 (3)
O2—C2—C1	108.3 (2)	O8—C12—C13	126.4 (3)
O2—C2—C3	108.6 (2)	O3—C12—C13	110.5 (3)
C1—C2—C3	102.2 (2)	C12—C13—H13A	109.5
O2—C2—H2A	112.4	C12—C13—H13B	109.5
C1—C2—H2A	112.4	H13A—C13—H13B	109.5
C3—C2—H2A	112.4	C12—C13—H13C	109.5
O3—C3—C7	113.3 (2)	H13A—C13—H13C	109.5
O3—C3—C4	104.26 (19)	H13B—C13—H13C	109.5
C7—C3—C4	111.4 (2)	O9—C14—O5	122.5 (3)
O3—C3—C2	116.0 (2)	O9—C14—C15	125.9 (3)
C7—C3—C2	110.0 (2)	O5—C14—C15	111.5 (3)
C4—C3—C2	101.2 (2)	C14—C15—H15A	109.5
O4—C4—C5	112.0 (2)	C14—C15—H15B	109.5
O4—C4—C3	103.7 (2)	H15A—C15—H15B	109.5
C5—C4—C3	112.6 (2)	C14—C15—H15C	109.5
O4—C4—H4A	109.4	H15A—C15—H15C	109.5
C5—C4—H4A	109.4	H15B—C15—H15C	109.5
C3—C4—H4A	109.4	N1—C16—C17	112.9 (2)
O5—C5—C6	108.9 (2)	N1—C16—H16A	109.0
O5—C5—C4	109.2 (2)	C17—C16—H16A	109.0
C6—C5—C4	112.3 (2)	N1—C16—H16B	109.0
O5—C5—H5A	108.8	C17—C16—H16B	109.0
C6—C5—H5A	108.8	H16A—C16—H16B	107.8
C4—C5—H5A	108.8	C22—C17—C18	117.5 (3)
N1—C6—C5	107.9 (2)	C22—C17—C16	122.0 (3)
N1—C6—H6A	110.1	C18—C17—C16	120.4 (3)
C5—C6—H6A	110.1	C19—C18—C17	120.4 (4)
N1—C6—H6B	110.1	C19—C18—H18A	119.8
C5—C6—H6B	110.1	C17—C18—H18A	119.8
H6A—C6—H6B	108.4	C20—C19—C18	120.3 (3)
N1—C7—C3	110.8 (2)	C20—C19—H19A	119.8
N1—C7—H7A	109.5	C18—C19—H19A	119.8
C3—C7—H7A	109.5	C21—C20—C19	119.9 (4)
N1—C7—H7B	109.5	C21—C20—H20A	120.0
C3—C7—H7B	109.5	C19—C20—H20A	120.0
H7A—C7—H7B	108.1	C20—C21—C22	120.2 (4)
O6—C8—O1	122.1 (3)	C20—C21—H21A	119.9
O6—C8—C9	126.7 (4)	C22—C21—H21A	119.9
O1—C8—C9	111.2 (4)	C17—C22—C21	121.7 (3)
C8—C9—H9A	109.5	C17—C22—H22A	119.2
C8—C9—H9B	109.5	C21—C22—H22A	119.2

C4—O4—C1—O1	−137.1 (2)	O4—C4—C5—C6	−67.2 (3)
C4—O4—C1—C2	−16.8 (3)	C3—C4—C5—C6	49.2 (3)
C8—O1—C1—O4	−78.8 (3)	C16—N1—C6—C5	−170.1 (2)
C8—O1—C1—C2	162.5 (2)	C7—N1—C6—C5	64.6 (3)
C10—O2—C2—C1	113.2 (3)	O5—C5—C6—N1	−178.5 (2)
C10—O2—C2—C3	−136.5 (2)	C4—C5—C6—N1	−57.5 (3)
O4—C1—C2—O2	105.0 (2)	C6—N1—C7—C3	−63.0 (3)
O1—C1—C2—O2	−136.5 (2)	C16—N1—C7—C3	171.1 (3)
O4—C1—C2—C3	−9.6 (3)	O3—C3—C7—N1	−65.2 (3)
O1—C1—C2—C3	109.0 (2)	C4—C3—C7—N1	51.9 (3)
C12—O3—C3—C7	−67.5 (3)	C2—C3—C7—N1	163.2 (2)
C12—O3—C3—C4	171.3 (2)	C1—O1—C8—O6	−1.0 (4)
C12—O3—C3—C2	61.0 (3)	C1—O1—C8—C9	179.9 (2)
O2—C2—C3—O3	27.8 (3)	C2—O2—C10—O7	0.3 (4)
C1—C2—C3—O3	142.1 (2)	C2—O2—C10—C11	179.3 (3)
O2—C2—C3—C7	157.9 (2)	C3—O3—C12—O8	−1.8 (4)
C1—C2—C3—C7	−87.8 (3)	C3—O3—C12—C13	177.9 (3)
O2—C2—C3—C4	−84.3 (2)	C5—O5—C14—O9	7.6 (5)
C1—C2—C3—C4	30.0 (2)	C5—O5—C14—C15	−170.2 (2)
C1—O4—C4—C5	158.4 (2)	C6—N1—C16—C17	76.4 (4)
C1—O4—C4—C3	36.7 (3)	C7—N1—C16—C17	−158.4 (3)
O3—C3—C4—O4	−161.9 (2)	N1—C16—C17—C22	33.4 (5)
C7—C3—C4—O4	75.6 (3)	N1—C16—C17—C18	−151.1 (4)
C2—C3—C4—O4	−41.2 (2)	C22—C17—C18—C19	0.5 (6)
O3—C3—C4—C5	76.7 (3)	C16—C17—C18—C19	−175.2 (4)
C7—C3—C4—C5	−45.7 (3)	C17—C18—C19—C20	0.6 (8)
C2—C3—C4—C5	−162.5 (2)	C18—C19—C20—C21	−1.8 (8)
C14—O5—C5—C6	−149.2 (2)	C19—C20—C21—C22	1.9 (7)
C14—O5—C5—C4	87.9 (3)	C18—C17—C22—C21	−0.5 (5)
O4—C4—C5—O5	53.6 (3)	C16—C17—C22—C21	175.2 (3)
C3—C4—C5—O5	170.1 (2)	C20—C21—C22—C17	−0.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O7	0.98	2.31	2.693 (3)	102
C5—H5A···O9	0.98	2.30	2.666 (4)	101
C7—H7A···O8	0.97	2.50	3.067 (4)	117
C15—H15C···O6ⁱ	0.96	2.33	3.161 (5)	144

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₇NO₉
M_r	449.45
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	291
a, b, c (Å)	8.1768 (16), 9.0613 (18), 15.591 (3)
β (°)	94.56 (3)
V (Å³)	1151.5 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Rigaku R-AXIS-IV diffractometer
Absorption correction	Multi-scan (SADABS: Sheldrick, 1996)
T_min, T_max	0.980, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	4341, 2503, 2173
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.107, 1.09
No. of reflections	2503
No. of parameters	290
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.13

Computer programs: R-AXIS II Software (Rigaku, 1997), 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
C2—H2A···O7	0.98	2.31	2.693 (3)	102
C5—H5A···O9	0.98	2.30	2.666 (4)	101
C7—H7A···O8	0.97	2.50	3.067 (4)	117
C15—H15C···O6ⁱ	0.96	2.33	3.161 (5)	144

Symmetry code: (i) x−1, y, z.

Acknowledgements

We gratefully acknowledge the financial support of the National Natural Science Foundation of China (20572103).

References

Compain, P. & Martin, O. R. (2001). Bioorg. Med. Chem. 9, 3077–3092. Web of Science CrossRef PubMed CAS Google Scholar
Compain, P. & Martin, O. R. (2003). Curr. Top. Med. Chem. 3, 541–560. Web of Science CrossRef PubMed CAS Google Scholar
Deshpandea, S. G. & Pathak, T. (2004). Tetrahedron Lett. 45, 2255–2258. Google Scholar
Guaragna, A., D'Alonzo, D., Paolella, C. & Palumbo, G. (2009). Tetrahedron Lett. 50, 2045–2047. CrossRef CAS Google Scholar
Rigaku (1997). R-AXIS II Software. Rigaku Corporation, Tokyo, Japan. Google Scholar
Saito, Y., Zevacob, T. A. & Agrofoglioa, L. A. (2002). Tetrahedron, 58, 9593–9603. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 6| June 2011| Page o1545

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-Benzyl-6-de­­oxy-3,6-imino­methyl­ene-1,2,3,5-O-tetra­acetyl-α-D-1(S)-epiallo­furan­ose

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

N-Benzyl-6-deoxy-3,6-iminomethylene-1,2,3,5-O-tetraacetyl-α-D-1(S)-epiallofuranose