3,4-Dicyano-phenyl 2,3,4,6-tetra-O-acetyl-α-d-glucopyran-oside.

The title compound, C(22)H(22)N(2)O(10), was prepared by the glycosidation method through nitrite displacement on substituted nitro-phthalonitrile. The mol-ecule contains a benzene ring, two nitrile groups and an acetyl-protected d-glucose fragment which adopts a chair conformation. The absolute configuration was determined by the use of d-glucose as starting material. All substituents of the protected sugar are in equatorial positions, with the exclusive presence of the α-anomer. The crystal packing is stabilized by C-H⋯O and C-H⋯N hydrogen-bonding inter-actions.

Related literature

For related literature, see: Alvarez-Mico et al. (2006 ▶, 2007 ▶); Burkhardt et al. (2007 ▶); Ribeiro et al. (2006 ▶); Huang et al. (2005 ▶); Dinçer et al. (2004 ▶); Berven et al. (1990 ▶); Ocak et al. (2004 ▶).

Experimental

Crystal data

C22H22N2O10

M = 474.42

Orthorhombic,

a = 8.175 (2) Å

b = 10.2076 (10) Å

c = 29.562 (6) Å

V = 2466.9 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 (2) K

0.6 × 0.5 × 0.1 mm

Data collection

Bruker P4 diffractometer

Absorption correction: none

5277 measured reflections

2639 independent reflections

1348 reflections with I > 2σ(I)

R int = 0.056

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.112

S = 1.06

2639 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: XSCANS (Bruker, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807049860/rz2165sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807049860/rz2165Isup2.hkl

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

C22H22N2O10	Dx = 1.277 Mg m−3
Mr = 474.42	Melting point = 159–160 K
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 46 reflections
a = 8.175 (2) Å	θ = 2.8–12.4º
b = 10.2076 (10) Å	µ = 0.10 mm−1
c = 29.562 (6) Å	T = 295 (2) K
V = 2466.9 (8) Å3	Plate, colorless
Z = 4	0.6 × 0.5 × 0.1 mm
F000 = 992

Bruker P4 diffractometer	Rint = 0.056
Radiation source: fine-focus sealed tube	θmax = 25.5º
Monochromator: graphite	θmin = 2.1º
T = 295(2) K	h = −9→9
ω scans	k = −12→12
Absorption correction: none	l = −35→35
5277 measured reflections	3 standard reflections
2639 independent reflections	every 97 reflections
1348 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.059	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.001P)2 + 0.8P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2639 reflections	Δρmax = 0.16 e Å−3
307 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.4684 (4)	0.4661 (4)	0.41414 (12)	0.0701 (11)
O2	0.3965 (4)	0.5287 (4)	0.34103 (13)	0.0670 (10)
O3	0.5901 (5)	0.7056 (4)	0.43421 (13)	0.0681 (10)
O4	0.4002 (7)	0.8623 (5)	0.43616 (17)	0.1139 (18)
O5	0.8048 (4)	0.7509 (4)	0.35957 (13)	0.0712 (11)
O6	1.0210 (5)	0.6471 (5)	0.38745 (18)	0.1015 (16)
O7	0.8182 (5)	0.5260 (4)	0.30029 (14)	0.0796 (12)
O8	0.8314 (7)	0.6754 (6)	0.2448 (2)	0.144 (2)
O9	0.4682 (5)	0.5005 (4)	0.24344 (15)	0.0786 (12)
O10	0.5851 (7)	0.3686 (5)	0.19353 (16)	0.1202 (19)
N1	−0.0545 (8)	−0.0194 (6)	0.4681 (2)	0.126 (2)
N2	−0.2037 (8)	0.2687 (7)	0.3913 (3)	0.152 (3)
C1	0.0363 (10)	0.0603 (7)	0.4593 (2)	0.093 (2)
C2	−0.0744 (9)	0.2681 (7)	0.4048 (3)	0.102 (3)
C3	0.1489 (8)	0.1642 (6)	0.4468 (2)	0.0793 (19)
C4	0.0938 (7)	0.2671 (6)	0.4191 (2)	0.0792 (18)
C5	0.1966 (7)	0.3700 (6)	0.4070 (2)	0.0753 (17)
H5A	0.1593	0.4382	0.3889	0.090*
C6	0.3586 (7)	0.3678 (6)	0.4229 (2)	0.0657 (16)
C7	0.4143 (8)	0.2645 (6)	0.4483 (2)	0.0771 (18)
H7A	0.5227	0.2631	0.4578	0.093*
C8	0.3113 (8)	0.1623 (6)	0.4598 (2)	0.086 (2)
H8A	0.3515	0.0919	0.4763	0.103*
C9	0.4184 (7)	0.5689 (5)	0.38547 (19)	0.0619 (15)
H9A	0.3145	0.6038	0.3968	0.074*
C10	0.5487 (6)	0.6784 (5)	0.38800 (19)	0.0591 (15)
H10A	0.5069	0.7580	0.3735	0.071*
C11	0.7051 (6)	0.6337 (5)	0.36433 (18)	0.0585 (14)
H11A	0.7621	0.5676	0.3825	0.070*
C12	0.6682 (7)	0.5818 (5)	0.31787 (19)	0.0654 (16)
H12A	0.6283	0.6519	0.2981	0.078*
C13	0.5412 (7)	0.4711 (5)	0.32161 (18)	0.0634 (15)
H13A	0.5831	0.4044	0.3425	0.076*
C14	0.5095 (9)	0.8067 (6)	0.4539 (2)	0.0795 (19)
C15	0.5743 (8)	0.8297 (6)	0.50044 (19)	0.096 (2)
H15A	0.5151	0.9003	0.5143	0.145*
H15B	0.6882	0.8519	0.4988	0.145*
H15C	0.5611	0.7516	0.5182	0.145*
C16	0.9631 (8)	0.7418 (7)	0.3712 (2)	0.0781 (18)
C17	1.0494 (8)	0.8681 (6)	0.3598 (2)	0.112 (3)
H17A	1.1629	0.8612	0.3678	0.168*
H17B	1.0004	0.9389	0.3763	0.168*
H17C	1.0398	0.8848	0.3279	0.168*
C18	0.8902 (9)	0.5880 (9)	0.2644 (3)	0.102 (3)
C19	1.0554 (7)	0.5319 (8)	0.2574 (3)	0.130 (3)
H19A	1.1076	0.5755	0.2325	0.194*
H19B	1.0462	0.4401	0.2509	0.194*
H19C	1.1196	0.5438	0.2843	0.194*
C20	0.5023 (8)	0.4075 (6)	0.27799 (19)	0.0785 (18)
H20A	0.5939	0.3534	0.2688	0.094*
H20B	0.4081	0.3508	0.2819	0.094*
C21	0.5168 (8)	0.4719 (7)	0.2017 (2)	0.0803 (18)
C22	0.4807 (12)	0.5694 (7)	0.1681 (2)	0.126 (3)
H22A	0.5217	0.5411	0.1393	0.189*
H22B	0.5318	0.6507	0.1763	0.189*
H22C	0.3645	0.5817	0.1662	0.189*

	U11	U22	U33	U12	U13	U23
O1	0.061 (2)	0.062 (2)	0.088 (3)	−0.007 (2)	−0.002 (2)	0.012 (2)
O2	0.058 (2)	0.065 (2)	0.078 (3)	−0.006 (2)	−0.002 (2)	−0.002 (2)
O3	0.072 (3)	0.069 (2)	0.064 (2)	0.007 (2)	−0.003 (2)	−0.005 (2)
O4	0.117 (4)	0.113 (4)	0.111 (4)	0.050 (4)	−0.010 (3)	−0.029 (3)
O5	0.057 (2)	0.065 (3)	0.091 (3)	−0.009 (2)	−0.005 (2)	0.008 (2)
O6	0.062 (3)	0.089 (3)	0.153 (4)	0.006 (3)	−0.017 (3)	0.007 (3)
O7	0.069 (3)	0.080 (3)	0.089 (3)	0.021 (3)	0.002 (2)	−0.007 (3)
O8	0.106 (4)	0.159 (5)	0.167 (6)	0.018 (4)	0.039 (4)	0.058 (5)
O9	0.092 (3)	0.071 (3)	0.072 (3)	0.011 (3)	0.000 (3)	−0.008 (2)
O10	0.153 (5)	0.099 (4)	0.108 (4)	0.027 (4)	0.019 (4)	−0.021 (3)
N1	0.121 (6)	0.075 (4)	0.181 (7)	−0.021 (4)	0.017 (5)	0.017 (4)
N2	0.077 (4)	0.114 (5)	0.266 (9)	−0.018 (5)	−0.039 (6)	0.042 (6)
C1	0.104 (6)	0.066 (4)	0.109 (5)	−0.010 (5)	0.005 (5)	0.004 (4)
C2	0.071 (5)	0.074 (5)	0.162 (7)	−0.012 (4)	−0.010 (5)	0.016 (5)
C3	0.082 (5)	0.056 (4)	0.101 (5)	−0.009 (4)	0.015 (4)	0.005 (4)
C4	0.071 (4)	0.058 (4)	0.109 (5)	−0.004 (4)	0.004 (4)	0.006 (4)
C5	0.076 (4)	0.063 (4)	0.086 (4)	−0.002 (4)	0.003 (4)	0.010 (4)
C6	0.067 (4)	0.060 (4)	0.070 (4)	−0.005 (3)	0.006 (3)	0.003 (3)
C7	0.079 (4)	0.066 (4)	0.086 (4)	0.003 (4)	−0.005 (4)	0.003 (4)
C8	0.087 (5)	0.063 (4)	0.107 (5)	0.004 (4)	−0.006 (4)	0.013 (4)
C9	0.057 (4)	0.061 (3)	0.068 (4)	−0.005 (3)	−0.001 (3)	0.004 (3)
C10	0.058 (4)	0.052 (3)	0.067 (4)	0.003 (3)	0.006 (3)	0.005 (3)
C11	0.051 (3)	0.054 (4)	0.070 (4)	0.000 (3)	−0.005 (3)	0.005 (3)
C12	0.060 (4)	0.060 (4)	0.076 (4)	0.010 (3)	−0.001 (3)	0.004 (3)
C13	0.065 (4)	0.056 (3)	0.069 (4)	0.007 (3)	−0.005 (3)	0.001 (3)
C14	0.076 (5)	0.071 (4)	0.092 (5)	−0.004 (4)	0.007 (4)	−0.001 (4)
C15	0.114 (6)	0.100 (5)	0.075 (4)	−0.009 (5)	−0.009 (4)	−0.007 (4)
C16	0.062 (4)	0.089 (5)	0.084 (5)	−0.006 (4)	0.005 (4)	−0.003 (4)
C17	0.097 (5)	0.109 (6)	0.130 (6)	−0.048 (5)	−0.012 (5)	0.001 (5)
C18	0.066 (5)	0.126 (8)	0.114 (7)	0.000 (5)	0.022 (5)	−0.002 (6)
C19	0.065 (5)	0.180 (8)	0.144 (7)	0.011 (6)	0.018 (5)	−0.035 (7)
C20	0.090 (5)	0.063 (4)	0.083 (4)	0.002 (4)	−0.013 (4)	−0.002 (4)
C21	0.092 (5)	0.072 (4)	0.077 (5)	−0.016 (4)	0.005 (4)	−0.007 (4)
C22	0.204 (9)	0.103 (5)	0.072 (4)	0.014 (7)	−0.009 (5)	0.010 (5)

O1—C6	1.371 (6)	C9—C10	1.546 (6)
O1—C9	1.409 (6)	C9—H9A	0.9800
O2—C9	1.388 (6)	C10—C11	1.528 (7)
O2—C13	1.441 (6)	C10—H10A	0.9800
O3—C14	1.355 (7)	C11—C12	1.503 (7)
O3—C10	1.434 (6)	C11—H11A	0.9800
O4—C14	1.182 (7)	C12—C13	1.539 (7)
O5—C16	1.343 (7)	C12—H12A	0.9800
O5—C11	1.454 (6)	C13—C20	1.478 (7)
O6—C16	1.178 (7)	C13—H13A	0.9800
O7—C18	1.369 (8)	C14—C15	1.493 (8)
O7—C12	1.449 (6)	C15—H15A	0.9600
O8—C18	1.168 (9)	C15—H15B	0.9600
O9—C21	1.327 (7)	C15—H15C	0.9600
O9—C20	1.422 (6)	C16—C17	1.509 (8)
O10—C21	1.218 (7)	C17—H17A	0.9600
N1—C1	1.132 (8)	C17—H17B	0.9600
N2—C2	1.130 (8)	C17—H17C	0.9600
C1—C3	1.452 (9)	C18—C19	1.481 (9)
C2—C4	1.439 (9)	C19—H19A	0.9600
C3—C8	1.382 (8)	C19—H19B	0.9600
C3—C4	1.407 (8)	C19—H19C	0.9600
C4—C5	1.392 (7)	C20—H20A	0.9700
C5—C6	1.406 (8)	C20—H20B	0.9700
C5—H5A	0.9300	C21—C22	1.438 (8)
C6—C7	1.371 (7)	C22—H22A	0.9600
C7—C8	1.383 (8)	C22—H22B	0.9600
C7—H7A	0.9300	C22—H22C	0.9600
C8—H8A	0.9300
C6—O1—C9	118.0 (4)	C13—C12—H12A	110.8
C9—O2—C13	113.1 (4)	O2—C13—C20	110.5 (5)
C14—O3—C10	116.2 (5)	O2—C13—C12	106.4 (4)
C16—O5—C11	117.3 (5)	C20—C13—C12	113.9 (5)
C18—O7—C12	117.4 (5)	O2—C13—H13A	108.6
C21—O9—C20	117.5 (5)	C20—C13—H13A	108.6
N1—C1—C3	178.0 (9)	C12—C13—H13A	108.6
N2—C2—C4	176.4 (10)	O4—C14—O3	122.9 (7)
C8—C3—C4	118.7 (6)	O4—C14—C15	127.0 (7)
C8—C3—C1	121.9 (7)	O3—C14—C15	110.1 (6)
C4—C3—C1	119.4 (6)	C14—C15—H15A	109.5
C5—C4—C3	121.3 (6)	C14—C15—H15B	109.5
C5—C4—C2	119.7 (6)	H15A—C15—H15B	109.5
C3—C4—C2	118.9 (6)	C14—C15—H15C	109.5
C4—C5—C6	118.1 (6)	H15A—C15—H15C	109.5
C4—C5—H5A	121.0	H15B—C15—H15C	109.5
C6—C5—H5A	121.0	O6—C16—O5	123.3 (7)
O1—C6—C7	116.7 (6)	O6—C16—C17	127.2 (6)
O1—C6—C5	122.8 (6)	O5—C16—C17	109.5 (6)
C7—C6—C5	120.6 (6)	C16—C17—H17A	109.5
C6—C7—C8	120.8 (6)	C16—C17—H17B	109.5
C6—C7—H7A	119.6	H17A—C17—H17B	109.5
C8—C7—H7A	119.6	C16—C17—H17C	109.5
C3—C8—C7	120.4 (6)	H17A—C17—H17C	109.5
C3—C8—H8A	119.8	H17B—C17—H17C	109.5
C7—C8—H8A	119.8	O8—C18—O7	124.1 (7)
O2—C9—O1	112.7 (4)	O8—C18—C19	127.0 (9)
O2—C9—C10	110.4 (4)	O7—C18—C19	108.8 (8)
O1—C9—C10	108.1 (4)	C18—C19—H19A	109.5
O2—C9—H9A	108.5	C18—C19—H19B	109.5
O1—C9—H9A	108.5	H19A—C19—H19B	109.5
C10—C9—H9A	108.5	C18—C19—H19C	109.5
O3—C10—C11	107.2 (4)	H19A—C19—H19C	109.5
O3—C10—C9	110.4 (4)	H19B—C19—H19C	109.5
C11—C10—C9	109.8 (4)	O9—C20—C13	112.1 (5)
O3—C10—H10A	109.8	O9—C20—H20A	109.2
C11—C10—H10A	109.8	C13—C20—H20A	109.2
C9—C10—H10A	109.8	O9—C20—H20B	109.2
O5—C11—C12	108.3 (4)	C13—C20—H20B	109.2
O5—C11—C10	105.5 (4)	H20A—C20—H20B	107.9
C12—C11—C10	110.8 (4)	O10—C21—O9	120.9 (7)
O5—C11—H11A	110.7	O10—C21—C22	123.8 (7)
C12—C11—H11A	110.7	O9—C21—C22	115.4 (7)
C10—C11—H11A	110.7	C21—C22—H22A	109.5
O7—C12—C11	107.3 (4)	C21—C22—H22B	109.5
O7—C12—C13	107.9 (4)	H22A—C22—H22B	109.5
C11—C12—C13	109.2 (4)	C21—C22—H22C	109.5
O7—C12—H12A	110.8	H22A—C22—H22C	109.5
C11—C12—H12A	110.8	H22B—C22—H22C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O2	0.93	2.57	3.016 (7)	110
C11—H11A···O6	0.98	2.27	2.675 (6)	103
C12—H12A···O8	0.98	2.30	2.713 (8)	104
C13—H13A···O1	0.98	2.40	2.800 (6)	104
C20—H20A···O10	0.97	2.23	2.617 (7)	102
C5—H5A···O6i	0.93	2.41	3.224 (8)	146
C9—H9A···O6i	0.98	2.46	3.346 (7)	151
C10—H10A···O10ii	0.98	2.40	3.283 (7)	149
C15—H15C···N1iii	0.96	2.58	3.465 (9)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O2	0.93	2.57	3.016 (7)	110
C11—H11A⋯O6	0.98	2.27	2.675 (6)	103
C12—H12A⋯O8	0.98	2.30	2.713 (8)	104
C13—H13A⋯O1	0.98	2.40	2.800 (6)	104
C20—H20A⋯O10	0.97	2.23	2.617 (7)	102
C5—H5A⋯O6i	0.93	2.41	3.224 (8)	146
C9—H9A⋯O6i	0.98	2.46	3.346 (7)	151
C10—H10A⋯O10ii	0.98	2.40	3.283 (7)	149
C15—H15C⋯N1iii	0.96	2.58	3.465 (9)	153

Symmetry codes: (i) ; (ii) ; (iii) .