3-Ethyl-8-meth­oxy-4-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranos­yloxy)quinolin-2(1H)-one

Kimmel, R.; Nečas, M.; Kafka, S.; Košmrlj, J.; Vícha, R.

doi:10.1107/S1600536810016636

Volume 66
Part 6
Pages o1328-o1329
June 2010

Received 14 April 2010
Accepted 6 May 2010
Online 12 May 2010

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.032
wR = 0.080
Data-to-parameter ratio = 8.9
Details

3-Ethyl-8-methoxy-4-(2,3,4,6-tetra-O-acetyl--D-glucopyranosyloxy)quinolin-2(1H)-one

Roman Kimmel,^a Marek Necas,^b Stanislav Kafka,^a Janez Kosmrlj ^c and Robert Vícha ^a ^*

^aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín,762 72, Czech Republic,^bDepartment of Chemistry, Faculty of Science, Masaryk University in Brno, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic, and ^cDepartment of Chemistry, Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, 1000 Ljubljana, Slovenia
Correspondence e-mail: rvicha@ft.utb.cz

The structure of the title compound, C₂₆H₃₁NO₁₂, contains an essentially planar quinoline skeleton, with the maximum deviation from the best plane being 0.055 (2) Å, and an oxane ring in a classical chair conformation with the following Cremer and Pople puckering parameters: Q = 0.586 (2) Å, [theta] = 11.5 (2)° and [varphi] = 309.4 (10)°. One acetyl group displays rotational disorder with occupancies of 0.634 (8):0.366 (8). The crystal packing is stabilized by N-HO hydrogen bonds, which link molecules into chains along the a axis. The packing is further stabilized by weak C-HO interactions. The absolute configurations on the carbons in the oxane ring correspond to those of the commercial starting material and are unchanged in the well known mechanism of the Koenigs-Knorr synthesis.

Related literature

For the synthesis of related compounds and their biological activity, see Kimmel et al. (2010); Suzuki et al. (2007). For puckering parameters, see Cremer & Pople (1975).

Experimental

Crystal data

C₂₆H₃₁NO₁₂
M_r = 549.52
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.36993 (11) Å
b = 19.2205 (6) Å
c = 27.2479 (6) Å
V = 2812.33 (11) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 150 K
0.40 × 0.40 × 0.30 mm

Data collection

Kuma KM-4 CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.918, T_max = 0.967
32021 measured reflections
3429 independent reflections
2990 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.080
S = 1.09
3429 reflections
387 parameters
81 restraints
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.88	1.98	2.831 (2)	163
C13-H13O9ⁱⁱ	1.00	2.39	3.292 (3)	149
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; 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 Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2031 ).

Acknowledgements

This study was supported by the Ministry of Education, Youth and Sports of the Czech Republic (project No. MSM7088352101 and joint project No. 9-06-3 of the KONTAKT Programme) and the Slovenian Research Agency (project No. P1-0230-0103 and joint project No. BI-CZ/07-08-018).

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Kimmel, R., Kafka, S. & Kosmrlj, J. (2010). Carbohydr. Res. 345, 768-779.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Suzuki, H., Aly, N. S. M., Wataya, Y., Kim, H.-S., Tamai, I., Kita, M. & Uemura, D. (2007). Chem. Pharm. Bull. 55, 821-824.

organic compounds