2,3,4,6-Tetra-O-acetyl-β-d-galacto-pyrano-syl butyrate.

The title compound, C(18)H(26)O(11), was synthesized by a condensation reaction of 2,3,4,6-tetra-O-acetyl-α-d-galactopyranosyl bromide and butyric acid. The acet-oxy-methyl and butyrate groups are located on the same side of the pyran ring, showing the β configuration for the d-glycosyl ester; the butyl group adopts an extend conformation, the C-C-C-C torsion angle being 179.1 (7)°. In the crystal, the mol-ecules are linked by weak C-H⋯O hydrogen bonds.

Related literature

For the total synthesis of glycosyl esters, see: Li et al. (1992 ▶); Smith et al. (1986 ▶). For the anti-tumor activities of glycosyl esters, see: Feldman et al. (2000 ▶). For related structures, see: Sambaiah et al. (2001 ▶); Parkanyi et al. (1987 ▶); Roslund et al. (2004 ▶); Liu et al. (2009 ▶); Kumar et al. (2005) ▶. For the synthesis, see: Loganathan & Trivedi (1987 ▶).

Experimental

Crystal data

C18H26O11

M = 418.39

Monoclinic,

a = 9.2079 (9) Å

b = 8.5034 (5) Å

c = 14.3199 (12) Å

β = 100.804 (9)°

V = 1101.35 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 294 K

0.38 × 0.32 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini Ultra diffractometer

6393 measured reflections

2160 independent reflections

1582 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.147

S = 1.03

2160 reflections

268 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055814/xu5405sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055814/xu5405Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055814/xu5405Isup3.cml

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

C18H26O11	F(000) = 444
Mr = 418.39	Dx = 1.262 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3799 reflections
a = 9.2079 (9) Å	θ = 3.2–26.4°
b = 8.5034 (5) Å	µ = 0.11 mm−1
c = 14.3199 (12) Å	T = 294 K
β = 100.804 (9)°	Block, colorless
V = 1101.35 (16) Å3	0.38 × 0.32 × 0.25 mm
Z = 2

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	1582 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 25.4°, θmin = 2.9°
Detector resolution: 10.3592 pixels mm-1	h = −11→8
ω scans	k = −10→9
6393 measured reflections	l = −16→17
2160 independent 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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0855P)2 + 0.0985P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.002
2160 reflections	Δρmax = 0.35 e Å−3
268 parameters	Δρmin = −0.21 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (6)

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	0.1960 (3)	0.9067 (3)	0.2033 (2)	0.0627 (8)
O2	0.2171 (3)	0.8828 (4)	0.3617 (2)	0.0669 (8)
O3	−0.0223 (5)	0.8472 (6)	0.3587 (3)	0.1095 (14)
O4	0.2776 (3)	1.2097 (3)	0.3854 (2)	0.0599 (7)
O5	0.4753 (4)	1.1092 (5)	0.4784 (2)	0.0989 (13)
O6	0.4015 (3)	1.3413 (3)	0.23619 (19)	0.0606 (7)
O7	0.2592 (4)	1.5007 (4)	0.1320 (3)	0.0843 (10)
O8	0.4303 (3)	1.0527 (3)	0.13984 (19)	0.0607 (7)
O9	0.5101 (5)	1.2274 (5)	0.0433 (3)	0.1129 (15)
O10	0.1343 (4)	1.0060 (4)	−0.0433 (2)	0.0778 (9)
O11	0.0730 (4)	0.8056 (4)	−0.1411 (2)	0.0833 (10)
C1	0.1872 (5)	0.9923 (5)	0.2865 (3)	0.0579 (10)
H1	0.0883	1.0375	0.2824	0.069*
C2	0.3038 (4)	1.1195 (5)	0.3053 (3)	0.0516 (9)
H2	0.4030	1.0731	0.3185	0.062*
C3	0.2868 (4)	1.2263 (4)	0.2199 (3)	0.0524 (10)
H3	0.1912	1.2800	0.2127	0.063*
C4	0.2904 (4)	1.1312 (5)	0.1311 (3)	0.0553 (10)
H4	0.2741	1.1999	0.0751	0.066*
C5	0.1711 (5)	1.0062 (5)	0.1214 (3)	0.0592 (10)
H5	0.0749	1.0579	0.1171	0.071*
C6	0.1034 (6)	0.8206 (6)	0.3940 (3)	0.0691 (12)
C7	0.1506 (7)	0.7109 (7)	0.4739 (3)	0.0898 (16)
H7A	0.2396	0.6558	0.4658	0.108*
H7B	0.0737	0.6338	0.4764	0.108*
C8	0.1820 (10)	0.8143 (11)	0.5717 (4)	0.139 (3)
H8A	0.2591	0.8907	0.5683	0.166*
H8B	0.0931	0.8714	0.5779	0.166*
C9	0.2258 (9)	0.7182 (11)	0.6526 (4)	0.135 (3)
H9A	0.3178	0.6677	0.6490	0.202*
H9B	0.1515	0.6398	0.6548	0.202*
H9C	0.2378	0.7817	0.7090	0.202*
C10	0.3699 (5)	1.1938 (6)	0.4686 (3)	0.0640 (11)
C11	0.3271 (7)	1.2933 (7)	0.5437 (3)	0.0857 (15)
H11A	0.2395	1.3516	0.5177	0.129*
H11B	0.4059	1.3650	0.5674	0.129*
H11C	0.3080	1.2280	0.5947	0.129*
C12	0.3736 (6)	1.4773 (5)	0.1855 (4)	0.0698 (12)
C13	0.4984 (7)	1.5887 (8)	0.2062 (5)	0.114 (2)
H13A	0.5798	1.5396	0.2476	0.171*
H13B	0.4683	1.6807	0.2364	0.171*
H13C	0.5283	1.6182	0.1479	0.171*
C14	0.1652 (6)	0.9010 (6)	0.0361 (3)	0.0709 (12)
H14A	0.2590	0.8479	0.0381	0.085*
H14B	0.0878	0.8229	0.0331	0.085*
C15	0.5298 (5)	1.1116 (6)	0.0906 (3)	0.0697 (12)
C16	0.6667 (5)	1.0135 (6)	0.1061 (4)	0.0839 (15)
H16A	0.7105	1.0135	0.1724	0.126*
H16B	0.7356	1.0562	0.0701	0.126*
H16C	0.6420	0.9077	0.0856	0.126*
C17	0.0882 (5)	0.9440 (6)	−0.1293 (3)	0.0653 (12)
C18	0.0590 (7)	1.0649 (8)	−0.2023 (3)	0.0884 (15)
H18A	0.1422	1.1347	−0.1960	0.133*
H18B	−0.0274	1.1233	−0.1950	0.133*
H18C	0.0429	1.0165	−0.2639	0.133*

	U11	U22	U33	U12	U13	U23
O1	0.0752 (19)	0.0537 (15)	0.0613 (17)	−0.0060 (14)	0.0180 (14)	0.0060 (14)
O2	0.0644 (18)	0.0700 (19)	0.0679 (18)	−0.0023 (15)	0.0161 (14)	0.0242 (16)
O3	0.083 (3)	0.128 (4)	0.126 (3)	−0.001 (2)	0.042 (2)	0.034 (3)
O4	0.0617 (17)	0.0651 (17)	0.0542 (15)	0.0114 (14)	0.0146 (12)	0.0022 (14)
O5	0.084 (2)	0.123 (3)	0.082 (2)	0.028 (3)	−0.0029 (19)	−0.015 (2)
O6	0.0665 (18)	0.0549 (16)	0.0591 (15)	−0.0089 (13)	0.0083 (13)	0.0000 (14)
O7	0.088 (2)	0.068 (2)	0.093 (2)	−0.0005 (18)	0.008 (2)	0.0190 (19)
O8	0.0660 (18)	0.0577 (15)	0.0618 (16)	0.0012 (13)	0.0209 (13)	0.0072 (14)
O9	0.110 (3)	0.112 (3)	0.131 (3)	0.010 (3)	0.061 (3)	0.055 (3)
O10	0.106 (2)	0.0663 (19)	0.0575 (17)	−0.0130 (18)	0.0052 (16)	0.0012 (16)
O11	0.086 (2)	0.080 (2)	0.079 (2)	0.0041 (19)	0.0024 (17)	−0.0216 (19)
C1	0.056 (2)	0.061 (2)	0.056 (2)	0.002 (2)	0.0102 (18)	0.009 (2)
C2	0.053 (2)	0.053 (2)	0.049 (2)	0.0056 (18)	0.0099 (16)	0.0022 (18)
C3	0.050 (2)	0.052 (2)	0.054 (2)	0.0009 (18)	0.0065 (17)	0.0065 (18)
C4	0.060 (2)	0.053 (2)	0.052 (2)	0.0007 (19)	0.0090 (17)	0.0099 (19)
C5	0.070 (3)	0.053 (2)	0.054 (2)	−0.006 (2)	0.0084 (19)	0.0048 (19)
C6	0.075 (3)	0.073 (3)	0.063 (3)	−0.003 (3)	0.023 (2)	0.005 (2)
C7	0.103 (4)	0.091 (3)	0.076 (3)	−0.020 (3)	0.018 (3)	0.024 (3)
C8	0.197 (9)	0.135 (6)	0.081 (4)	0.022 (6)	0.016 (5)	0.021 (4)
C9	0.153 (7)	0.160 (8)	0.095 (4)	−0.013 (6)	0.033 (4)	−0.010 (5)
C10	0.063 (3)	0.070 (3)	0.062 (3)	−0.003 (2)	0.018 (2)	0.004 (2)
C11	0.114 (4)	0.087 (3)	0.061 (3)	−0.007 (3)	0.028 (3)	−0.007 (3)
C12	0.082 (3)	0.056 (3)	0.075 (3)	−0.010 (2)	0.023 (3)	0.002 (2)
C13	0.125 (5)	0.087 (4)	0.122 (5)	−0.041 (4)	0.005 (4)	0.014 (4)
C14	0.089 (3)	0.057 (2)	0.064 (3)	−0.008 (2)	0.007 (2)	0.004 (2)
C15	0.078 (3)	0.065 (3)	0.073 (3)	−0.014 (2)	0.030 (2)	−0.003 (3)
C16	0.075 (3)	0.080 (3)	0.106 (4)	0.000 (3)	0.040 (3)	−0.010 (3)
C17	0.059 (3)	0.076 (3)	0.061 (3)	−0.004 (2)	0.012 (2)	−0.006 (2)
C18	0.097 (4)	0.101 (4)	0.066 (3)	0.002 (3)	0.012 (3)	0.005 (3)

O1—C1	1.412 (5)	C7—C8	1.634 (9)
O1—C5	1.429 (5)	C7—H7A	0.9700
O2—C6	1.331 (5)	C7—H7B	0.9700
O2—C1	1.412 (5)	C8—C9	1.413 (9)
O3—C6	1.195 (6)	C8—H8A	0.9700
O4—C10	1.334 (5)	C8—H8B	0.9700
O4—C2	1.437 (5)	C9—H9A	0.9600
O5—C10	1.195 (6)	C9—H9B	0.9600
O6—C12	1.363 (5)	C9—H9C	0.9600
O6—C3	1.426 (5)	C10—C11	1.478 (7)
O7—C12	1.197 (6)	C11—H11A	0.9600
O8—C15	1.353 (5)	C11—H11B	0.9600
O8—C4	1.435 (5)	C11—H11C	0.9600
O9—C15	1.190 (6)	C12—C13	1.476 (7)
O10—C17	1.334 (5)	C13—H13A	0.9600
O10—C14	1.432 (5)	C13—H13B	0.9600
O11—C17	1.193 (6)	C13—H13C	0.9600
C1—C2	1.513 (6)	C14—H14A	0.9700
C1—H1	0.9800	C14—H14B	0.9700
C2—C3	1.507 (5)	C15—C16	1.492 (7)
C2—H2	0.9800	C16—H16A	0.9600
C3—C4	1.513 (6)	C16—H16B	0.9600
C3—H3	0.9800	C16—H16C	0.9600
C4—C5	1.516 (6)	C17—C18	1.454 (7)
C4—H4	0.9800	C18—H18A	0.9600
C5—C14	1.506 (6)	C18—H18B	0.9600
C5—H5	0.9800	C18—H18C	0.9600
C6—C7	1.477 (7)
C1—O1—C5	111.2 (3)	H8A—C8—H8B	108.0
C6—O2—C1	118.3 (3)	C8—C9—H9A	109.5
C10—O4—C2	119.0 (3)	C8—C9—H9B	109.5
C12—O6—C3	115.7 (3)	H9A—C9—H9B	109.5
C15—O8—C4	117.8 (3)	C8—C9—H9C	109.5
C17—O10—C14	118.0 (4)	H9A—C9—H9C	109.5
O2—C1—O1	105.7 (3)	H9B—C9—H9C	109.5
O2—C1—C2	107.8 (3)	O5—C10—O4	122.2 (4)
O1—C1—C2	111.6 (3)	O5—C10—C11	125.5 (4)
O2—C1—H1	110.6	O4—C10—C11	112.3 (4)
O1—C1—H1	110.6	C10—C11—H11A	109.5
C2—C1—H1	110.6	C10—C11—H11B	109.5
O4—C2—C3	108.6 (3)	H11A—C11—H11B	109.5
O4—C2—C1	107.7 (3)	C10—C11—H11C	109.5
C3—C2—C1	108.9 (3)	H11A—C11—H11C	109.5
O4—C2—H2	110.5	H11B—C11—H11C	109.5
C3—C2—H2	110.5	O7—C12—O6	122.5 (4)
C1—C2—H2	110.5	O7—C12—C13	125.5 (5)
O6—C3—C2	108.6 (3)	O6—C12—C13	112.0 (4)
O6—C3—C4	111.8 (3)	C12—C13—H13A	109.5
C2—C3—C4	110.2 (3)	C12—C13—H13B	109.5
O6—C3—H3	108.7	H13A—C13—H13B	109.5
C2—C3—H3	108.7	C12—C13—H13C	109.5
C4—C3—H3	108.7	H13A—C13—H13C	109.5
O8—C4—C3	109.6 (3)	H13B—C13—H13C	109.5
O8—C4—C5	107.7 (3)	O10—C14—C5	104.2 (3)
C3—C4—C5	108.8 (3)	O10—C14—H14A	110.9
O8—C4—H4	110.2	C5—C14—H14A	110.9
C3—C4—H4	110.2	O10—C14—H14B	110.9
C5—C4—H4	110.2	C5—C14—H14B	110.9
O1—C5—C14	106.8 (3)	H14A—C14—H14B	108.9
O1—C5—C4	109.7 (3)	O9—C15—O8	123.8 (5)
C14—C5—C4	113.9 (4)	O9—C15—C16	125.6 (5)
O1—C5—H5	108.8	O8—C15—C16	110.6 (4)
C14—C5—H5	108.8	C15—C16—H16A	109.5
C4—C5—H5	108.8	C15—C16—H16B	109.5
O3—C6—O2	122.7 (4)	H16A—C16—H16B	109.5
O3—C6—C7	124.6 (5)	C15—C16—H16C	109.5
O2—C6—C7	112.6 (5)	H16A—C16—H16C	109.5
C6—C7—C8	107.7 (5)	H16B—C16—H16C	109.5
C6—C7—H7A	110.2	O11—C17—O10	121.9 (5)
C8—C7—H7A	110.2	O11—C17—C18	126.5 (5)
C6—C7—H7B	110.2	O10—C17—C18	111.6 (4)
C8—C7—H7B	110.2	C17—C18—H18A	109.5
H7A—C7—H7B	108.5	C17—C18—H18B	109.5
C9—C8—C7	111.6 (7)	H18A—C18—H18B	109.5
C9—C8—H8A	109.3	C17—C18—H18C	109.5
C7—C8—H8A	109.3	H18A—C18—H18C	109.5
C9—C8—H8B	109.3	H18B—C18—H18C	109.5
C7—C8—H8B	109.3
C6—O2—C1—O1	−99.1 (4)	C1—O1—C5—C14	−173.6 (3)
C6—O2—C1—C2	141.5 (4)	C1—O1—C5—C4	62.5 (4)
C5—O1—C1—O2	−178.6 (3)	O8—C4—C5—O1	59.6 (4)
C5—O1—C1—C2	−61.7 (4)	C3—C4—C5—O1	−59.2 (4)
C10—O4—C2—C3	−134.7 (4)	O8—C4—C5—C14	−60.1 (4)
C10—O4—C2—C1	107.5 (4)	C3—C4—C5—C14	−178.9 (3)
O2—C1—C2—O4	−69.9 (4)	C1—O2—C6—O3	4.1 (7)
O1—C1—C2—O4	174.5 (3)	C1—O2—C6—C7	−178.8 (4)
O2—C1—C2—C3	172.6 (3)	O3—C6—C7—C8	−96.6 (7)
O1—C1—C2—C3	57.0 (4)	O2—C6—C7—C8	86.3 (6)
C12—O6—C3—C2	−156.7 (3)	C6—C7—C8—C9	179.1 (7)
C12—O6—C3—C4	81.5 (4)	C2—O4—C10—O5	1.4 (7)
O4—C2—C3—O6	65.8 (4)	C2—O4—C10—C11	−179.6 (4)
C1—C2—C3—O6	−177.2 (3)	C3—O6—C12—O7	1.4 (6)
O4—C2—C3—C4	−171.4 (3)	C3—O6—C12—C13	−179.5 (5)
C1—C2—C3—C4	−54.4 (4)	C17—O10—C14—C5	−164.4 (4)
C15—O8—C4—C3	−104.4 (4)	O1—C5—C14—O10	177.8 (3)
C15—O8—C4—C5	137.4 (4)	C4—C5—C14—O10	−60.9 (5)
O6—C3—C4—O8	59.4 (4)	C4—O8—C15—O9	2.7 (7)
C2—C3—C4—O8	−61.5 (4)	C4—O8—C15—C16	−178.6 (4)
O6—C3—C4—C5	177.0 (3)	C14—O10—C17—O11	−0.2 (7)
C2—C3—C4—C5	56.1 (4)	C14—O10—C17—C18	179.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O11i	0.98	2.47	3.362 (5)	152
C5—H5···O11i	0.98	2.57	3.443 (6)	149
C11—H11B···O5ii	0.96	2.49	3.293 (7)	141
C16—H16C···O9iii	0.96	2.60	3.441 (7)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O11i	0.98	2.47	3.362 (5)	152
C5—H5⋯O11i	0.98	2.57	3.443 (6)	149
C11—H11B⋯O5ii	0.96	2.49	3.293 (7)	141
C16—H16C⋯O9iii	0.96	2.60	3.441 (7)	147

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