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

The galactose 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 features C-H⋯O inter-actions that lead to the formation of supra-molecular layers in the ab plane.

Related literature

For the synthesis, see: Benassi et al. (2007 ▶); Patil et al. (2008 ▶). For the biological activity of related structures, see: Zheng et al. (2010 ▶). For the structure of the isomeric allopyran­oside and glucopyran­oside derivatives, see: Ye et al. (2009 ▶); Heidelberg et al. (2011 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C21H24O11

M = 452.40

Monoclinic,

a = 11.8358 (4) Å

b = 5.6664 (2) Å

c = 17.5079 (6) Å

β = 109.616 (4)°

V = 1106.05 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.25 × 0.20 × 0.05 mm

Data collection

Agilent Supernova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.596, T max = 1.000

10396 measured reflections

2768 independent reflections

2535 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.086

S = 1.05

2768 reflections

293 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 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/S1600536811008257/ez2236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008257/ez2236Isup2.hkl

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

C21H24O11	F(000) = 476
Mr = 452.40	Dx = 1.358 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5487 reflections
a = 11.8358 (4) Å	θ = 2.5–29.3°
b = 5.6664 (2) Å	µ = 0.11 mm−1
c = 17.5079 (6) Å	T = 100 K
β = 109.616 (4)°	Prism, colourless
V = 1106.05 (7) Å3	0.25 × 0.20 × 0.05 mm
Z = 2

Agilent Supernova Dual diffractometer with an Atlas detector	2768 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2535 reflections with I > 2σ(I)
Mirror	Rint = 0.051
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −7→6
Tmin = 0.596, Tmax = 1.000	l = −22→16
10396 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0424P)2 + 0.1621P] where P = (Fo2 + 2Fc2)/3
2768 reflections	(Δ/σ)max < 0.001
293 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

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	0.52081 (12)	0.4982 (3)	0.29215 (8)	0.0188 (3)
O2	0.48738 (13)	0.0896 (3)	0.37091 (9)	0.0240 (4)
O3	0.55891 (13)	−0.1643 (3)	0.47497 (9)	0.0243 (4)
O4	0.75837 (12)	0.6298 (3)	0.39447 (8)	0.0184 (3)
O5	0.86847 (14)	0.3841 (3)	0.49186 (9)	0.0283 (4)
O6	0.83224 (12)	0.7065 (3)	0.26663 (8)	0.0202 (3)
O7	0.95682 (14)	0.3988 (3)	0.27801 (9)	0.0271 (4)
O8	0.61785 (14)	0.7131 (3)	0.12877 (9)	0.0202 (3)
O9	0.61716 (16)	1.1080 (3)	0.13951 (10)	0.0304 (4)
O10	0.41232 (13)	0.7100 (3)	0.18039 (8)	0.0213 (3)
O11	−0.15194 (15)	0.5245 (5)	0.06218 (12)	0.0490 (6)
C1	0.61385 (17)	0.3269 (4)	0.32349 (12)	0.0180 (4)
H1	0.6016	0.1990	0.2821	0.022*
C2	0.73547 (18)	0.4392 (4)	0.33610 (12)	0.0178 (4)
H2	0.8001	0.3174	0.3549	0.021*
C3	0.73421 (17)	0.5437 (4)	0.25518 (12)	0.0177 (4)
H3	0.7421	0.4124	0.2191	0.021*
C4	0.62145 (17)	0.6840 (4)	0.21135 (11)	0.0177 (4)
H4	0.6253	0.8420	0.2376	0.021*
C5	0.50894 (18)	0.5541 (4)	0.21107 (12)	0.0182 (4)
H5	0.4966	0.4081	0.1772	0.022*
C6	0.59907 (18)	0.2203 (4)	0.39814 (12)	0.0216 (5)
H6A	0.6670	0.1138	0.4253	0.026*
H6B	0.5958	0.3454	0.4368	0.026*
C7	0.47923 (18)	−0.0968 (4)	0.41586 (12)	0.0205 (4)
C8	0.35738 (19)	−0.2058 (5)	0.38251 (13)	0.0272 (5)
H8A	0.3622	−0.3731	0.3974	0.041*
H8B	0.3277	−0.1909	0.3233	0.041*
H8C	0.3024	−0.1247	0.4049	0.041*
C9	0.83088 (18)	0.5785 (4)	0.47134 (12)	0.0195 (4)
C10	0.8534 (2)	0.7915 (4)	0.52407 (13)	0.0246 (5)
H10A	0.9152	0.7559	0.5762	0.037*
H10B	0.7791	0.8375	0.5332	0.037*
H10C	0.8807	0.9212	0.4976	0.037*
C11	0.94103 (19)	0.6087 (5)	0.27887 (12)	0.0221 (5)
C12	1.0356 (2)	0.7935 (5)	0.29539 (14)	0.0301 (6)
H12A	1.0988	0.7413	0.2746	0.045*
H12B	1.0701	0.8202	0.3540	0.045*
H12C	1.0003	0.9407	0.2684	0.045*
C13	0.61949 (19)	0.9346 (4)	0.10083 (13)	0.0208 (5)
C14	0.6223 (2)	0.9316 (5)	0.01601 (13)	0.0284 (5)
H14A	0.6497	1.0852	0.0034	0.043*
H14B	0.5416	0.8993	−0.0219	0.043*
H14C	0.6774	0.8081	0.0111	0.043*
C15	0.29775 (18)	0.6182 (5)	0.16131 (12)	0.0214 (5)
C16	0.2083 (2)	0.7649 (5)	0.11247 (13)	0.0269 (5)
H16	0.2281	0.9110	0.0935	0.032*
C17	0.0891 (2)	0.6936 (5)	0.09193 (14)	0.0310 (6)
H17	0.0271	0.7924	0.0588	0.037*
C18	0.0601 (2)	0.4804 (5)	0.11914 (13)	0.0282 (5)
C19	0.1514 (2)	0.3361 (5)	0.16730 (13)	0.0275 (5)
H19	0.1317	0.1889	0.1856	0.033*
C20	0.27087 (19)	0.4037 (4)	0.18905 (13)	0.0246 (5)
H20	0.3328	0.3050	0.2222	0.030*
C21	−0.0667 (2)	0.4052 (6)	0.09904 (14)	0.0369 (6)
H21	−0.0816	0.2530	0.1163	0.044*

	U11	U22	U33	U12	U13	U23
O1	0.0204 (7)	0.0207 (8)	0.0147 (7)	0.0044 (6)	0.0053 (6)	0.0017 (6)
O2	0.0208 (7)	0.0267 (9)	0.0219 (7)	−0.0005 (7)	0.0037 (6)	0.0064 (7)
O3	0.0241 (7)	0.0252 (9)	0.0233 (7)	−0.0009 (7)	0.0075 (6)	0.0057 (7)
O4	0.0216 (7)	0.0151 (7)	0.0159 (6)	0.0016 (6)	0.0025 (6)	−0.0009 (6)
O5	0.0353 (9)	0.0198 (9)	0.0226 (7)	0.0033 (7)	0.0000 (7)	0.0025 (7)
O6	0.0205 (7)	0.0175 (8)	0.0231 (7)	−0.0019 (6)	0.0081 (6)	−0.0008 (6)
O7	0.0248 (8)	0.0258 (10)	0.0309 (8)	0.0023 (7)	0.0095 (7)	0.0016 (8)
O8	0.0305 (8)	0.0153 (8)	0.0149 (7)	0.0001 (7)	0.0078 (6)	−0.0004 (6)
O9	0.0498 (10)	0.0161 (8)	0.0268 (8)	−0.0001 (8)	0.0148 (8)	0.0009 (8)
O10	0.0211 (7)	0.0181 (8)	0.0220 (7)	0.0049 (6)	0.0035 (6)	0.0020 (7)
O11	0.0240 (9)	0.0789 (17)	0.0400 (11)	0.0101 (10)	0.0052 (8)	−0.0055 (11)
C1	0.0201 (9)	0.0133 (10)	0.0193 (9)	0.0013 (9)	0.0048 (8)	0.0014 (8)
C2	0.0214 (10)	0.0131 (11)	0.0181 (9)	0.0008 (8)	0.0054 (8)	−0.0015 (8)
C3	0.0189 (10)	0.0142 (11)	0.0200 (10)	−0.0020 (8)	0.0064 (8)	−0.0014 (8)
C4	0.0238 (10)	0.0151 (11)	0.0144 (9)	0.0020 (9)	0.0065 (8)	0.0005 (8)
C5	0.0218 (10)	0.0146 (11)	0.0168 (9)	0.0034 (8)	0.0048 (8)	0.0008 (8)
C6	0.0197 (10)	0.0224 (12)	0.0204 (10)	−0.0029 (9)	0.0039 (8)	0.0039 (9)
C7	0.0219 (10)	0.0206 (11)	0.0217 (10)	−0.0018 (9)	0.0107 (9)	−0.0013 (9)
C8	0.0241 (11)	0.0309 (14)	0.0266 (11)	−0.0053 (10)	0.0087 (9)	0.0010 (11)
C9	0.0172 (9)	0.0210 (12)	0.0180 (9)	−0.0019 (9)	0.0027 (8)	0.0022 (9)
C10	0.0272 (11)	0.0224 (12)	0.0200 (10)	0.0011 (10)	0.0024 (9)	−0.0004 (10)
C11	0.0230 (10)	0.0270 (13)	0.0167 (9)	−0.0005 (10)	0.0072 (8)	−0.0005 (10)
C12	0.0255 (11)	0.0358 (15)	0.0290 (11)	−0.0071 (11)	0.0092 (10)	−0.0055 (11)
C13	0.0214 (10)	0.0174 (12)	0.0222 (10)	0.0005 (9)	0.0056 (9)	0.0034 (9)
C14	0.0380 (12)	0.0267 (14)	0.0215 (10)	0.0039 (11)	0.0113 (10)	0.0041 (10)
C15	0.0213 (10)	0.0248 (12)	0.0170 (9)	0.0027 (9)	0.0050 (8)	−0.0051 (9)
C16	0.0297 (12)	0.0280 (13)	0.0216 (10)	0.0069 (10)	0.0067 (10)	0.0003 (10)
C17	0.0243 (11)	0.0433 (16)	0.0222 (10)	0.0113 (11)	0.0036 (9)	−0.0008 (11)
C18	0.0252 (11)	0.0389 (15)	0.0201 (10)	0.0029 (11)	0.0070 (9)	−0.0085 (11)
C19	0.0269 (11)	0.0276 (13)	0.0279 (11)	−0.0027 (10)	0.0091 (10)	−0.0070 (10)
C20	0.0227 (10)	0.0235 (12)	0.0250 (10)	0.0036 (10)	0.0046 (9)	−0.0003 (10)
C21	0.0257 (12)	0.0567 (19)	0.0284 (12)	0.0004 (13)	0.0092 (10)	−0.0121 (13)

O1—C5	1.415 (2)	C7—C8	1.496 (3)
O1—C1	1.432 (2)	C8—H8A	0.9800
O2—C7	1.340 (3)	C8—H8B	0.9800
O2—C6	1.449 (3)	C8—H8C	0.9800
O3—C7	1.205 (3)	C9—C10	1.488 (3)
O4—C9	1.362 (2)	C10—H10A	0.9800
O4—C2	1.448 (2)	C10—H10B	0.9800
O5—C9	1.197 (3)	C10—H10C	0.9800
O6—C11	1.351 (3)	C11—C12	1.489 (3)
O6—C3	1.443 (2)	C12—H12A	0.9800
O7—C11	1.205 (3)	C12—H12B	0.9800
O8—C13	1.350 (3)	C12—H12C	0.9800
O8—C4	1.441 (2)	C13—C14	1.497 (3)
O9—C13	1.199 (3)	C14—H14A	0.9800
O10—C15	1.384 (3)	C14—H14B	0.9800
O10—C5	1.401 (2)	C14—H14C	0.9800
O11—C21	1.206 (3)	C15—C20	1.385 (3)
C1—C6	1.502 (3)	C15—C16	1.391 (3)
C1—C2	1.521 (3)	C16—C17	1.393 (3)
C1—H1	1.0000	C16—H16	0.9500
C2—C3	1.531 (3)	C17—C18	1.384 (4)
C2—H2	1.0000	C17—H17	0.9500
C3—C4	1.521 (3)	C18—C19	1.391 (3)
C3—H3	1.0000	C18—C21	1.484 (3)
C4—C5	1.520 (3)	C19—C20	1.389 (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	109.93 (14)	H8B—C8—H8C	109.5
C7—O2—C6	116.57 (16)	O5—C9—O4	122.7 (2)
C9—O4—C2	116.39 (17)	O5—C9—C10	126.07 (19)
C11—O6—C3	116.03 (17)	O4—C9—C10	111.22 (19)
C13—O8—C4	118.07 (17)	C9—C10—H10A	109.5
C15—O10—C5	117.57 (17)	C9—C10—H10B	109.5
O1—C1—C6	107.86 (16)	H10A—C10—H10B	109.5
O1—C1—C2	109.91 (17)	C9—C10—H10C	109.5
C6—C1—C2	115.02 (17)	H10A—C10—H10C	109.5
O1—C1—H1	107.9	H10B—C10—H10C	109.5
C6—C1—H1	107.9	O7—C11—O6	123.1 (2)
C2—C1—H1	107.9	O7—C11—C12	125.9 (2)
O4—C2—C1	111.00 (16)	O6—C11—C12	110.9 (2)
O4—C2—C3	107.82 (17)	C11—C12—H12A	109.5
C1—C2—C3	108.23 (16)	C11—C12—H12B	109.5
O4—C2—H2	109.9	H12A—C12—H12B	109.5
C1—C2—H2	109.9	C11—C12—H12C	109.5
C3—C2—H2	109.9	H12A—C12—H12C	109.5
O6—C3—C4	105.32 (16)	H12B—C12—H12C	109.5
O6—C3—C2	111.18 (16)	O9—C13—O8	123.49 (19)
C4—C3—C2	113.79 (16)	O9—C13—C14	125.6 (2)
O6—C3—H3	108.8	O8—C13—C14	110.91 (19)
C4—C3—H3	108.8	C13—C14—H14A	109.5
C2—C3—H3	108.8	C13—C14—H14B	109.5
O8—C4—C5	108.73 (16)	H14A—C14—H14B	109.5
O8—C4—C3	106.93 (15)	C13—C14—H14C	109.5
C5—C4—C3	111.57 (17)	H14A—C14—H14C	109.5
O8—C4—H4	109.9	H14B—C14—H14C	109.5
C5—C4—H4	109.9	O10—C15—C20	124.53 (19)
C3—C4—H4	109.9	O10—C15—C16	113.9 (2)
O10—C5—O1	108.61 (15)	C20—C15—C16	121.5 (2)
O10—C5—C4	107.29 (17)	C15—C16—C17	118.7 (2)
O1—C5—C4	108.26 (16)	C15—C16—H16	120.6
O10—C5—H5	110.9	C17—C16—H16	120.6
O1—C5—H5	110.9	C18—C17—C16	120.8 (2)
C4—C5—H5	110.9	C18—C17—H17	119.6
O2—C6—C1	106.20 (16)	C16—C17—H17	119.6
O2—C6—H6A	110.5	C17—C18—C19	119.3 (2)
C1—C6—H6A	110.5	C17—C18—C21	121.1 (2)
O2—C6—H6B	110.5	C19—C18—C21	119.5 (3)
C1—C6—H6B	110.5	C20—C19—C18	121.1 (2)
H6A—C6—H6B	108.7	C20—C19—H19	119.5
O3—C7—O2	124.39 (19)	C18—C19—H19	119.5
O3—C7—C8	125.4 (2)	C15—C20—C19	118.6 (2)
O2—C7—C8	110.25 (18)	C15—C20—H20	120.7
C7—C8—H8A	109.5	C19—C20—H20	120.7
C7—C8—H8B	109.5	O11—C21—C18	124.3 (3)
H8A—C8—H8B	109.5	O11—C21—H21	117.8
C7—C8—H8C	109.5	C18—C21—H21	117.8
H8A—C8—H8C	109.5
C5—O1—C1—C6	−163.31 (17)	C3—C4—C5—O1	54.5 (2)
C5—O1—C1—C2	70.6 (2)	C7—O2—C6—C1	151.59 (18)
C9—O4—C2—C1	100.1 (2)	O1—C1—C6—O2	66.5 (2)
C9—O4—C2—C3	−141.53 (17)	C2—C1—C6—O2	−170.44 (17)
O1—C1—C2—O4	61.5 (2)	C6—O2—C7—O3	−2.2 (3)
C6—C1—C2—O4	−60.5 (2)	C6—O2—C7—C8	177.27 (18)
O1—C1—C2—C3	−56.7 (2)	C2—O4—C9—O5	−4.5 (3)
C6—C1—C2—C3	−178.60 (18)	C2—O4—C9—C10	176.56 (17)
C11—O6—C3—C4	−158.49 (16)	C3—O6—C11—O7	2.3 (3)
C11—O6—C3—C2	77.8 (2)	C3—O6—C11—C12	−176.14 (16)
O4—C2—C3—O6	44.2 (2)	C4—O8—C13—O9	−4.2 (3)
C1—C2—C3—O6	164.33 (16)	C4—O8—C13—C14	176.78 (17)
O4—C2—C3—C4	−74.5 (2)	C5—O10—C15—C20	17.7 (3)
C1—C2—C3—C4	45.6 (2)	C5—O10—C15—C16	−164.09 (18)
C13—O8—C4—C5	120.0 (2)	O10—C15—C16—C17	−177.76 (19)
C13—O8—C4—C3	−119.44 (19)	C20—C15—C16—C17	0.5 (3)
O6—C3—C4—O8	73.70 (19)	C15—C16—C17—C18	−0.3 (3)
C2—C3—C4—O8	−164.29 (17)	C16—C17—C18—C19	−0.2 (3)
O6—C3—C4—C5	−167.54 (16)	C16—C17—C18—C21	178.7 (2)
C2—C3—C4—C5	−45.5 (2)	C17—C18—C19—C20	0.6 (3)
C15—O10—C5—O1	−74.1 (2)	C21—C18—C19—C20	−178.3 (2)
C15—O10—C5—C4	169.11 (16)	O10—C15—C20—C19	177.9 (2)
C1—O1—C5—O10	176.18 (16)	C16—C15—C20—C19	−0.2 (3)
C1—O1—C5—C4	−67.6 (2)	C18—C19—C20—C15	−0.4 (3)
O8—C4—C5—O10	−70.80 (19)	C17—C18—C21—O11	−3.8 (4)
C3—C4—C5—O10	171.51 (15)	C19—C18—C21—O11	175.1 (2)
O8—C4—C5—O1	172.16 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O9i	1.00	2.39	3.199 (3)	137
C5—H5···O9i	1.00	2.45	3.268 (3)	139
C10—H10b···O3ii	0.98	2.46	3.307 (3)	145
C12—H12b···O5iii	0.98	2.57	3.548 (3)	172
C14—H14c···O11iv	0.98	2.50	3.415 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O9i	1.00	2.39	3.199 (3)	137
C5—H5⋯O9i	1.00	2.45	3.268 (3)	139
C10—H10b⋯O3ii	0.98	2.46	3.307 (3)	145
C12—H12b⋯O5iii	0.98	2.57	3.548 (3)	172
C14—H14c⋯O11iv	0.98	2.50	3.415 (4)	155

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