1,5-Anhydro-2-de­oxy-1,2-C-dichloro­methyl­ene-3,4,6-tri-O-(4-meth­oxy­benz­yl)-d-glycero-d-gulo-hexitol

Kinfe, H.H.; Moshapo, P.T.; Muller, A.

doi:10.1107/S1600536811026870

Volume 67
Part 8
Pages o2012-o2013
August 2011

Received 10 June 2011
Accepted 5 July 2011
Online 13 July 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.023
wR = 0.062
Data-to-parameter ratio = 12.9
Details

1,5-Anhydro-2-deoxy-1,2-C-dichloromethylene-3,4,6-tri-O-(4-methoxybenzyl)-D-glycero-D-gulo-hexitol

Henok H. Kinfe,^a ^* Paseka T. Moshapo ^a and Alfred Muller ^a ^*

^aResearch Center in Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg 2006, South Africa
Correspondence e-mail: hhkinfe@uj.ac.za, mullera@uj.ac.za

The pyranosyl ring in the title compound, C₃₁H₃₄Cl₂O₇, adopts a twist-boat conformation. The 4-methoxybenzyl groups are located in equatorial positions with the methoxy groups nearly coplanar with their respective rings [dihedral angles of 0.2 (3) and 9.4 (2)°]. The aromatic rings adopt orientations enabling them to participate in C-H [pi] interactions with neighboring methoxy groups. The crystal structure is additionally stabilized by weak C-HO interactions.

Related literature

For the synthesis and chemistry of cyclopropanated carbohydrates, see: Cousins & Hoberg (2000); Yu & Pagenkopf (2005). For the modified Simmons-Smith reaction route of preparing cyclopropanated sugars, see: Gammon et al. (2007); Ramana et al. (1997); Murali et al. (1995); Boeckman et al. (1987); Hoberg & Bozell (1995). For the dihalocarbene cyclopropanation route, see: Gammon et al. (2007); Ramana et al. (1997); Murali et al. (1995); Brimacombe et al. (1967); Weber & Hall (1979). For the diazocyclopropanation route, see: Hoberg & Claffey (1996); Henry & Fraser-Reid (1995); Timmers et al. (1996). For ring puckering analysis, see: Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₃₁H₃₄Cl₂O₇
M_r = 589.48
Monoclinic, P 2₁
a = 5.3480 (4) Å
b = 18.1110 (14) Å
c = 14.8230 (11) Å
= 91.162 (2)°
V = 1435.43 (19) Å³
Z = 2
Mo K radiation
= 0.27 mm^-1
T = 100 K
0.53 × 0.44 × 0.39 mm

Data collection

Bruker KappaCCD APEX DUO 4K diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.869, T_max = 0.901
13864 measured reflections
4689 independent reflections
4635 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.023
wR(F²) = 0.062
S = 1.04
4689 reflections
364 parameters
1 restraint
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 1023 Friedel pairs
Flack parameter: 0.03 (3)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C17-C22, C9-C14 and C25-C30 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C4-H4O1ⁱ	1.00	2.38	3.3487 (16)	164
C23-H23BO7ⁱⁱ	0.98	2.50	3.399 (2)	153
C26-H26O3ⁱ	0.95	2.54	3.2301 (16)	130
C31-H31CO1ⁱⁱⁱ	0.98	2.49	3.466 (2)	172
C15-H15ACg1^iv	0.98	2.95	3.927 (3)	174
C15-H15CCg2^v	0.98	2.99	3.873 (2)	151
C24-H24BCg3^v	0.99	2.90	3.7983 (17)	152
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z+1; (iii) $[-x, y+{\script{1\over 2}}, -z]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (v) x+1, y, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus and XPREP (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2012 ).

Acknowledgements

Research funds of the University of Johannesburg and the Center for Synthesis and Catalysis are gratefully acknowledged. Mr C. Ncube is thanked for the data collection.

References

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organic compounds