N-Benzyl-6-de-oxy-3,6-imino-methyl-ene-1,2,3,5-O-tetra-acetyl-α-d-1(S)-epiallo-furan-ose.

The mol-ecule of the title compound, C(22)H(27)NO(9), 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 inter-planar angle between the five- and six-membered rings is 65.69 (11)°. The crystal structure is stablized by weak inter-molecular 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 = 449.45

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.107

S = 1.09

2503 reflections

290 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.13 e Å−3

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.

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

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

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

C22H27NO9	F(000) = 476
Mr = 449.45	Dx = 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

Rigaku R-AXIS-IV diffractometer	2503 independent reflections
Radiation source: fine-focus sealed tube	2173 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 0 pixels mm-1	θmax = 26.5°, θmin = 1.3°
Oscillation frames scans	h = 0→10
Absorption correction: multi-scan (SADABS: Sheldrick, 1996)	k = −11→11
Tmin = 0.980, Tmax = 0.984	l = −19→19
4341 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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0659P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2503 reflections	Δρmax = 0.15 e Å−3
290 parameters	Δρmin = −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)

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	0.1159 (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*

	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)

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)

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

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) .