4-Formyl-phenyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyran-oside.

The pyran-oside ring in the title compound, C(21)H(24)O(11), has a chair conformation with the substituted benzene ring occupying an equatorial position. The crystal packing is dominated by C-H⋯O inter-actions that lead to the formation of supra-molecular layers in the ab plane.

Related literature

For synthesis, see: Bao et al. (2004 ▶); Hongu et al. (1999 ▶); Patil & Ravindranathan Kartha (2008 ▶). For the natural anti-oxidant glucosyl­ated resveratrol, see: La Torre et al. (2004 ▶). For the biological activity of related structures, see: Wen et al. (2008 ▶); Yan et al. (2009 ▶). For the structure of the isomeric allopyran­oside and galactose derivatives, see: Ye et al. (2009 ▶); Hussen et al. (2011 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C21H24O11

M = 452.40

Triclinic,

a = 5.7868 (2) Å

b = 8.9166 (3) Å

c = 11.4716 (3) Å

α = 102.473 (3)°

β = 93.481 (2)°

γ = 102.780 (3)°

V = 559.96 (3) Å3

Z = 1

Cu Kα radiation

μ = 0.94 mm−1

T = 100 K

0.30 × 0.30 × 0.20 mm

Data collection

Agilent Supernova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010 ▶) T min = 0.919, T max = 1.000

7392 measured reflections

4097 independent reflections

4087 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.07

4097 reflections

293 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1855 Friedel pairs

Flack parameter: -0.02(12)

Data collection: CrysAlis PRO (Agilent Technologies, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008099/ez2235sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008099/ez2235Isup2.hkl

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

C21H24O11	Z = 1
Mr = 452.40	F(000) = 238
Triclinic, P1	Dx = 1.342 Mg m−3
Hall symbol: P 1	Cu Kα radiation, λ = 1.54184 Å
a = 5.7868 (2) Å	Cell parameters from 7285 reflections
b = 8.9166 (3) Å	θ = 4.0–74.1°
c = 11.4716 (3) Å	µ = 0.94 mm−1
α = 102.473 (3)°	T = 100 K
β = 93.481 (2)°	Block, colourless
γ = 102.780 (3)°	0.30 × 0.30 × 0.20 mm
V = 559.96 (3) Å3

Agilent Supernova Dual diffractometer with an Atlas detector	4097 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4087 reflections with I > 2σ(I)
Mirror	Rint = 0.021
Detector resolution: 10.4041 pixels mm-1	θmax = 74.3°, θmin = 4.0°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	k = −9→10
Tmin = 0.919, Tmax = 1.000	l = −13→14
7392 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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0908P)2 + 0.072P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
4097 reflections	Δρmax = 0.27 e Å−3
293 parameters	Δρmin = −0.17 e Å−3
3 restraints	Absolute structure: Flack (1983), 1855 Friedel pairs
Primary atom site location: structure-invariant direct methods

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	0.9987 (2)	0.49931 (15)	0.49910 (11)	0.0174 (3)
O2	1.0120 (2)	0.81529 (16)	0.57609 (11)	0.0218 (3)
O3	0.7432 (3)	0.95346 (19)	0.63881 (14)	0.0305 (3)
O4	0.7892 (2)	0.55996 (15)	0.20730 (10)	0.0167 (3)
O5	0.4356 (2)	0.59974 (16)	0.26001 (12)	0.0208 (3)
O6	0.7723 (2)	0.23423 (15)	0.15960 (11)	0.0192 (3)
O7	1.0136 (3)	0.2794 (2)	0.01679 (14)	0.0385 (4)
O8	1.1640 (2)	0.17486 (15)	0.30105 (11)	0.0196 (3)
O9	0.8768 (3)	−0.04604 (17)	0.28892 (15)	0.0297 (3)
O10	1.1933 (2)	0.31718 (15)	0.54454 (11)	0.0204 (3)
O11	2.0808 (3)	0.73176 (19)	0.92751 (14)	0.0330 (4)
C1	0.9617 (3)	0.5930 (2)	0.41525 (15)	0.0166 (3)
H1	1.1190	0.6460	0.3937	0.020*
C2	0.8116 (3)	0.4800 (2)	0.30264 (15)	0.0155 (3)
H2	0.6503	0.4316	0.3225	0.019*
C3	0.9368 (3)	0.3515 (2)	0.25138 (15)	0.0163 (3)
H3	1.0817	0.3980	0.2159	0.020*
C4	1.0071 (3)	0.2710 (2)	0.34749 (16)	0.0171 (3)
H4	0.8624	0.2051	0.3712	0.021*
C5	1.1452 (3)	0.3968 (2)	0.45629 (15)	0.0168 (3)
H5	1.2968	0.4572	0.4343	0.020*
C6	0.8401 (3)	0.7168 (2)	0.47781 (16)	0.0187 (3)
H6A	0.7979	0.7799	0.4222	0.022*
H6B	0.6930	0.6665	0.5080	0.022*
C7	0.9388 (3)	0.9279 (2)	0.65168 (16)	0.0220 (4)
C8	1.1278 (4)	1.0105 (3)	0.75474 (18)	0.0291 (4)
H8A	1.1138	1.1193	0.7845	0.044*
H8B	1.2855	1.0119	0.7277	0.044*
H8C	1.1077	0.9543	0.8194	0.044*
C9	0.5824 (3)	0.6053 (2)	0.19069 (15)	0.0163 (3)
C10	0.5674 (3)	0.6549 (3)	0.07482 (17)	0.0234 (4)
H10A	0.4287	0.7001	0.0685	0.035*
H10B	0.5507	0.5627	0.0077	0.035*
H10C	0.7128	0.7344	0.0721	0.035*
C11	0.8311 (4)	0.2113 (2)	0.04513 (17)	0.0250 (4)
C12	0.6319 (5)	0.0922 (3)	−0.0371 (2)	0.0428 (6)
H12A	0.6747	0.0749	−0.1195	0.064*
H12B	0.4866	0.1315	−0.0340	0.064*
H12C	0.6041	−0.0078	−0.0117	0.064*
C13	1.0775 (3)	0.0158 (2)	0.27726 (16)	0.0214 (4)
C14	1.2625 (4)	−0.0679 (3)	0.2328 (3)	0.0385 (5)
H14A	1.1877	−0.1802	0.1990	0.058*
H14B	1.3833	−0.0573	0.2997	0.058*
H14C	1.3381	−0.0212	0.1706	0.058*
C15	1.3937 (3)	0.3914 (2)	0.62530 (15)	0.0185 (4)
C16	1.5446 (4)	0.2974 (3)	0.64956 (18)	0.0230 (4)
H16	1.5095	0.1883	0.6104	0.028*
C17	1.7455 (4)	0.3644 (3)	0.73110 (18)	0.0249 (4)
H17	1.8490	0.3008	0.7482	0.030*
C18	1.7984 (3)	0.5252 (2)	0.78886 (16)	0.0229 (4)
C19	1.6452 (3)	0.6178 (2)	0.76354 (15)	0.0216 (4)
H19	1.6803	0.7268	0.8028	0.026*
C20	1.4427 (3)	0.5528 (2)	0.68196 (16)	0.0209 (4)
H20	1.3390	0.6162	0.6647	0.025*
C21	2.0148 (4)	0.5937 (3)	0.87497 (18)	0.0279 (4)
H21	2.1099	0.5244	0.8905	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0207 (6)	0.0178 (6)	0.0153 (5)	0.0077 (5)	0.0026 (4)	0.0040 (5)
O2	0.0222 (6)	0.0195 (7)	0.0197 (6)	0.0055 (5)	−0.0015 (5)	−0.0030 (5)
O3	0.0332 (8)	0.0268 (8)	0.0305 (7)	0.0149 (6)	0.0023 (6)	−0.0032 (6)
O4	0.0163 (6)	0.0200 (6)	0.0160 (5)	0.0071 (4)	0.0020 (4)	0.0061 (4)
O5	0.0175 (6)	0.0221 (7)	0.0231 (6)	0.0063 (5)	0.0035 (5)	0.0043 (5)
O6	0.0202 (6)	0.0176 (6)	0.0160 (6)	0.0022 (5)	−0.0017 (5)	−0.0006 (5)
O7	0.0419 (9)	0.0422 (9)	0.0211 (7)	−0.0038 (7)	0.0091 (6)	−0.0018 (6)
O8	0.0178 (6)	0.0166 (6)	0.0245 (6)	0.0057 (5)	0.0023 (5)	0.0034 (5)
O9	0.0278 (7)	0.0171 (7)	0.0435 (8)	0.0040 (5)	0.0079 (6)	0.0062 (6)
O10	0.0231 (6)	0.0186 (7)	0.0203 (6)	0.0041 (5)	−0.0020 (5)	0.0083 (5)
O11	0.0293 (7)	0.0380 (9)	0.0279 (7)	0.0037 (6)	−0.0054 (6)	0.0066 (6)
C1	0.0191 (8)	0.0156 (9)	0.0157 (8)	0.0049 (6)	0.0017 (6)	0.0041 (6)
C2	0.0167 (7)	0.0166 (9)	0.0148 (7)	0.0051 (6)	0.0034 (6)	0.0054 (6)
C3	0.0162 (8)	0.0156 (8)	0.0150 (7)	0.0027 (6)	−0.0006 (6)	0.0013 (6)
C4	0.0170 (8)	0.0148 (8)	0.0189 (8)	0.0043 (6)	0.0022 (6)	0.0022 (6)
C5	0.0183 (8)	0.0166 (9)	0.0164 (7)	0.0052 (6)	0.0010 (6)	0.0048 (6)
C6	0.0189 (8)	0.0167 (8)	0.0182 (8)	0.0039 (6)	0.0004 (6)	0.0000 (6)
C7	0.0286 (10)	0.0169 (9)	0.0206 (9)	0.0073 (7)	0.0045 (7)	0.0024 (7)
C8	0.0365 (11)	0.0227 (10)	0.0228 (9)	0.0043 (8)	−0.0018 (8)	−0.0014 (7)
C9	0.0154 (8)	0.0147 (8)	0.0176 (8)	0.0043 (6)	−0.0011 (6)	0.0012 (6)
C10	0.0244 (9)	0.0298 (10)	0.0189 (8)	0.0116 (7)	0.0008 (6)	0.0075 (7)
C11	0.0334 (10)	0.0234 (10)	0.0172 (8)	0.0073 (8)	0.0028 (7)	0.0017 (7)
C12	0.0504 (14)	0.0434 (14)	0.0206 (10)	−0.0062 (11)	−0.0034 (9)	−0.0024 (9)
C13	0.0243 (9)	0.0171 (9)	0.0224 (8)	0.0046 (7)	−0.0001 (7)	0.0048 (7)
C14	0.0350 (11)	0.0218 (11)	0.0614 (16)	0.0118 (9)	0.0152 (10)	0.0073 (10)
C15	0.0191 (8)	0.0225 (10)	0.0161 (8)	0.0054 (7)	0.0032 (6)	0.0084 (6)
C16	0.0263 (9)	0.0229 (9)	0.0238 (8)	0.0090 (7)	0.0049 (7)	0.0102 (7)
C17	0.0243 (9)	0.0309 (11)	0.0258 (9)	0.0124 (8)	0.0043 (7)	0.0139 (8)
C18	0.0228 (9)	0.0310 (11)	0.0175 (8)	0.0068 (7)	0.0035 (7)	0.0101 (7)
C19	0.0254 (9)	0.0233 (10)	0.0160 (8)	0.0065 (7)	0.0019 (7)	0.0041 (7)
C20	0.0240 (9)	0.0229 (10)	0.0180 (8)	0.0085 (7)	0.0014 (7)	0.0070 (7)
C21	0.0223 (9)	0.0400 (13)	0.0235 (9)	0.0075 (8)	0.0010 (7)	0.0120 (9)

O1—C5	1.413 (2)	C7—C8	1.499 (3)
O1—C1	1.439 (2)	C8—H8A	0.9800
O2—C7	1.340 (2)	C8—H8B	0.9800
O2—C6	1.443 (2)	C8—H8C	0.9800
O3—C7	1.210 (3)	C9—C10	1.492 (2)
O4—C9	1.361 (2)	C10—H10A	0.9800
O4—C2	1.443 (2)	C10—H10B	0.9800
O5—C9	1.199 (2)	C10—H10C	0.9800
O6—C11	1.360 (2)	C11—C12	1.497 (3)
O6—C3	1.4389 (19)	C12—H12A	0.9800
O7—C11	1.197 (3)	C12—H12B	0.9800
O8—C13	1.356 (2)	C12—H12C	0.9800
O8—C4	1.431 (2)	C13—C14	1.489 (3)
O9—C13	1.199 (3)	C14—H14A	0.9800
O10—C15	1.381 (2)	C14—H14B	0.9800
O10—C5	1.404 (2)	C14—H14C	0.9800
O11—C21	1.212 (3)	C15—C16	1.391 (3)
C1—C6	1.513 (2)	C15—C20	1.403 (3)
C1—C2	1.534 (2)	C16—C17	1.380 (3)
C1—H1	1.0000	C16—H16	0.9500
C2—C3	1.521 (2)	C17—C18	1.400 (3)
C2—H2	1.0000	C17—H17	0.9500
C3—C4	1.520 (2)	C18—C19	1.396 (3)
C3—H3	1.0000	C18—C21	1.472 (3)
C4—C5	1.527 (2)	C19—C20	1.384 (3)
C4—H4	1.0000	C19—H19	0.9500
C5—H5	1.0000	C20—H20	0.9500
C6—H6A	0.9900	C21—H21	0.9500
C6—H6B	0.9900
C5—O1—C1	111.07 (12)	H8B—C8—H8C	109.5
C7—O2—C6	116.65 (14)	O5—C9—O4	122.82 (15)
C9—O4—C2	117.18 (13)	O5—C9—C10	127.05 (16)
C11—O6—C3	117.74 (14)	O4—C9—C10	110.10 (14)
C13—O8—C4	117.05 (14)	C9—C10—H10A	109.5
C15—O10—C5	115.77 (13)	C9—C10—H10B	109.5
O1—C1—C6	106.88 (13)	H10A—C10—H10B	109.5
O1—C1—C2	107.27 (13)	C9—C10—H10C	109.5
C6—C1—C2	113.52 (14)	H10A—C10—H10C	109.5
O1—C1—H1	109.7	H10B—C10—H10C	109.5
C6—C1—H1	109.7	O7—C11—O6	124.08 (17)
C2—C1—H1	109.7	O7—C11—C12	126.49 (19)
O4—C2—C3	104.57 (13)	O6—C11—C12	109.41 (17)
O4—C2—C1	111.42 (13)	C11—C12—H12A	109.5
C3—C2—C1	110.19 (13)	C11—C12—H12B	109.5
O4—C2—H2	110.2	H12A—C12—H12B	109.5
C3—C2—H2	110.2	C11—C12—H12C	109.5
C1—C2—H2	110.2	H12A—C12—H12C	109.5
O6—C3—C2	107.91 (13)	H12B—C12—H12C	109.5
O6—C3—C4	108.09 (14)	O9—C13—O8	123.37 (18)
C2—C3—C4	111.16 (13)	O9—C13—C14	125.80 (19)
O6—C3—H3	109.9	O8—C13—C14	110.81 (17)
C2—C3—H3	109.9	C13—C14—H14A	109.5
C4—C3—H3	109.9	C13—C14—H14B	109.5
O8—C4—C3	108.55 (14)	H14A—C14—H14B	109.5
O8—C4—C5	107.52 (13)	C13—C14—H14C	109.5
C3—C4—C5	109.22 (14)	H14A—C14—H14C	109.5
O8—C4—H4	110.5	H14B—C14—H14C	109.5
C3—C4—H4	110.5	O10—C15—C16	116.66 (17)
C5—C4—H4	110.5	O10—C15—C20	122.13 (16)
O10—C5—O1	109.38 (13)	C16—C15—C20	121.21 (17)
O10—C5—C4	106.87 (14)	C17—C16—C15	119.31 (19)
O1—C5—C4	108.50 (13)	C17—C16—H16	120.3
O10—C5—H5	110.7	C15—C16—H16	120.3
O1—C5—H5	110.7	C16—C17—C18	120.59 (17)
C4—C5—H5	110.7	C16—C17—H17	119.7
O2—C6—C1	105.19 (14)	C18—C17—H17	119.7
O2—C6—H6A	110.7	C19—C18—C17	119.37 (17)
C1—C6—H6A	110.7	C19—C18—C21	121.21 (18)
O2—C6—H6B	110.7	C17—C18—C21	119.42 (18)
C1—C6—H6B	110.7	C20—C19—C18	120.91 (18)
H6A—C6—H6B	108.8	C20—C19—H19	119.5
O3—C7—O2	123.64 (17)	C18—C19—H19	119.5
O3—C7—C8	125.73 (18)	C19—C20—C15	118.61 (17)
O2—C7—C8	110.58 (16)	C19—C20—H20	120.7
C7—C8—H8A	109.5	C15—C20—H20	120.7
C7—C8—H8B	109.5	O11—C21—C18	124.9 (2)
H8A—C8—H8B	109.5	O11—C21—H21	117.5
C7—C8—H8C	109.5	C18—C21—H21	117.5
H8A—C8—H8C	109.5
C5—O1—C1—C6	−170.55 (13)	C3—C4—C5—O1	58.77 (17)
C5—O1—C1—C2	67.38 (15)	C7—O2—C6—C1	−174.96 (14)
C9—O4—C2—C3	140.73 (14)	O1—C1—C6—O2	64.96 (16)
C9—O4—C2—C1	−100.26 (16)	C2—C1—C6—O2	−176.99 (13)
O1—C1—C2—O4	−173.01 (13)	C6—O2—C7—O3	−2.8 (3)
C6—C1—C2—O4	69.16 (17)	C6—O2—C7—C8	174.88 (15)
O1—C1—C2—C3	−57.40 (16)	C2—O4—C9—O5	9.6 (2)
C6—C1—C2—C3	−175.23 (13)	C2—O4—C9—C10	−168.33 (15)
C11—O6—C3—C2	117.13 (16)	C3—O6—C11—O7	2.1 (3)
C11—O6—C3—C4	−122.56 (16)	C3—O6—C11—C12	−176.77 (19)
O4—C2—C3—O6	−69.99 (15)	C4—O8—C13—O9	2.9 (3)
C1—C2—C3—O6	170.17 (13)	C4—O8—C13—C14	−178.48 (17)
O4—C2—C3—C4	171.65 (13)	C5—O10—C15—C16	−134.15 (17)
C1—C2—C3—C4	51.81 (18)	C5—O10—C15—C20	46.8 (2)
C13—O8—C4—C3	−110.11 (16)	O10—C15—C16—C17	−178.90 (15)
C13—O8—C4—C5	131.85 (15)	C20—C15—C16—C17	0.2 (3)
O6—C3—C4—O8	73.14 (16)	C15—C16—C17—C18	−0.2 (3)
C2—C3—C4—O8	−168.61 (13)	C16—C17—C18—C19	0.2 (3)
O6—C3—C4—C5	−169.91 (13)	C16—C17—C18—C21	−179.67 (17)
C2—C3—C4—C5	−51.66 (18)	C17—C18—C19—C20	−0.2 (3)
C15—O10—C5—O1	−89.74 (17)	C21—C18—C19—C20	179.63 (17)
C15—O10—C5—C4	152.99 (14)	C18—C19—C20—C15	0.2 (3)
C1—O1—C5—O10	175.14 (12)	O10—C15—C20—C19	178.82 (15)
C1—O1—C5—C4	−68.62 (16)	C16—C15—C20—C19	−0.2 (3)
O8—C4—C5—O10	−65.78 (16)	C19—C18—C21—O11	−1.9 (3)
C3—C4—C5—O10	176.62 (13)	C17—C18—C21—O11	177.97 (19)
O8—C4—C5—O1	176.37 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O5i	1.00	2.51	3.356 (2)	143
C3—H3···O5i	1.00	2.35	3.207 (2)	143
C6—H6A···O9ii	0.99	2.40	3.324 (2)	155
C8—H8C···O11iii	0.98	2.54	3.475 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O5i	1.00	2.51	3.356 (2)	143
C3—H3⋯O5i	1.00	2.35	3.207 (2)	143
C6—H6A⋯O9ii	0.99	2.40	3.324 (2)	155
C8—H8C⋯O11iii	0.98	2.54	3.475 (3)	160

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