3-(6-Benz-yloxy-2,2-dimethyl-perhydro-furo[2,3-d][1,3]dioxol-5-yl)-5-(4-bromo-phen-yl)-2-phenyl-perhydro-pyrrolo[3,4-d]isoxazole-4,6-dione.

Abstract

In the title compound, C(31)H(29)BrN(2)O(7), the isoxazolidine ring adopts a twist conformation, while the tetrahydrofuran, dioxolone and pyrrole rings adopt envelope conformations. The structure is stabilized by inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Full text

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3-(6-Benzyloxy-2,2-dimethylperhydro-
furo[2,3-d][1,3]dioxol-5-yl)-5-(4-bromo-
phenyl)-2-phenylperhydropyrrolo[3,4-d]-
isoxazole-4,6-dione
M. NizamMohideen,aM. Damodiran,bA. SubbiahPandic*
and P. T. Perumalb
aDepartment of Physics, The New College (Autonomous), Chennai 600 014, India,
bOrganic Chemistry Division, Central Leather Research Institute, Chennai 600 020,
India, andcDepartment of Physics, Presidency College (Autonomous), Chennai 600
005, India
Correspondence e-mail: a_spandian@yahoo.com
Received 16 April 2009; accepted 23 April 2009
Key indicators: single-crystal X-ray study; T = 293 K; mean ?(C–C) = 0.004 A ˚;
R factor = 0.042; wR factor = 0.138; data-to-parameter ratio = 24.2.
In the title compound, C31H29BrN2O7, the isoxazolidine ring
adopts a twist conformation, while the tetrahydrofuran,
dioxolone and pyrrole rings adopt envelope conformations.
The structure is stabilized by intermolecular C—H???O
hydrogen bonds and C—H???? interactions.
Related literature
For general background to isoxazolidines, see: Ali et al. (1988);
Goti et al. (1997); Kumar et al. (2003); Huisgen (1984). For ring
puckering parameters see: Cremer & Pople (1975); Nardelli
(1983).
Experimental
Crystal data
C31H29BrN2O7
Mr= 621.47
Monoclinic, P21
a = 15.0680 (12) A˚
b = 6.6801 (5) A˚
c = 15.8550 (12) A˚
? = 117.578 (2)?
V = 1414.57 (19) A˚3
Z = 2
Mo K? radiation
? = 1.51 mm?1
T = 293 K
0.3 ? 0.2 ? 0.2 mm
Data collection
Bruker Kappa APEXII CCD
diffractometer
Absorption correction: multi-scan
(SADABS; Bruker 2004)
Tmin= 0.734, Tmax= 0.740
20450 measured reflections
9003 independent reflections
5502 reflections with I > 2?(I)
Rint= 0.027
Refinement
R[F2> 2?(F2)] = 0.042
wR(F2) = 0.138
S = 1.00
9003 reflections
372 parameters
1 restraint
H-atom parameters constrained
??max= 0.66 e A˚?3
??min= ?0.38 e A˚?3
Absolute structure: Flack (1983),
3886 Friedel pairs
Flack parameter: ?0.001 (8)
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
C1—H1???O2i
C5—H5???O5ii
C9—H9???O1ii
C19—H19B???O3i
C17—H17b???Cg1iii
C21—H21???Cg2iv
Symmetry codes: (i) x;y þ 1;z; (ii) ?x þ 2;y ?1
?x;y ?1
respectively.
D—HH???AD???AD—H???A
0.93
0.93
0.98
0.97
0.96
0.93
2.46
2.52
2.58
2.58
2.86
2.67
3.273 (3)
3.198 (3)
3.418 (3)
3.360 (3)
3.720 (4)
3.559 (7)
145
130
144
137
150
160
2;?z þ 1; (iii) ?x;y ?1
2;?z þ 1; (iv)
2;?z. Cg1 and Cg2 are the centroids of the C1–C6 and C20–C25 rings,
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2
and SAINT (Bruker, 2004); data reduction: SAINT and XPREP
(Bruker, 2004); program(s) used to solve structure: SHELXS97
(Sheldrick, 2008); program(s) used to refine structure: SHELXL97
(Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997);
software used to prepare material for publication: SHELXL97 and
PLATON (Spek, 2009).
MNM and ASP thank Dr J. Jothi Kumar, The Principal,
Presidency College (Autonomous), Chennai, India, for
providing the computer and internet facilities. The authors
thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his
help in collecting the X-ray intensity data.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: BT2932).
References
Ali, A. S., Khan, J. H. & Wazeer, M. I. M. (1988). Tetrahedron, 44, 5911–5920.
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc.,
Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Goti, A., Fedi, V., Naneli, L., De Sarlo, F. & Brandi, A. (1997). Synlett, pp. 577-
579.
Huisgen, R. (1984). 1,3-Dipolar Cycloaddition Chemistry, Vol. I, edited by A.
Padawa, pp. 3–27. New York: Wiley Interscience.
Kumar, K. R. R., Mallesha, H. & Rangappa, K. S. (2003). Synth. Commun. 33,
1545–1555.
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
organic compounds
o1156
NizamMohideen et al.
doi:10.1107/S1600536809015104
Acta Cryst. (2009). E65, o1156
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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supplementary materials

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supplementary materials
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Acta Cryst. (2009). E65, o1156 [ doi:10.1107/S1600536809015104 ]
3-(6-Benzyloxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl)-5-(4-bromophenyl)-2-phenylpe-
rhydropyrrolo[3,4-d]isoxazole-4,6-dione
M. NizamMohideen, M. Damodiran, A. SubbiahPandi and P. T. Perumal
Comment
Isoxazolidines are potential precursors for biologically important compounds such as amino sugars (Ali et al., 1988), alkal-
oids (Goti et al., 1997), and exhibit antibacterial and antifungal activities (Kumar et al., 2003). The stereochemistry, such as
regioselectivity and enantioselectivity, of heterocyclic isoxazole compounds (Huisgen, 1984) can be studied by 1,3-dipolar
cycloaddition reactions. In view of these important properties, the crystal structure of the title compound, (I), has been
determined.
A perspective view of compound (I) with the atom-numbering scheme is shown in Fig. 1. The dihedral angle between
the phenyl rings C1—C6 and C20—C25, and, C20—C25 and C26—C31, C1—C6 and C26—C31 are 62.4 (1), 75.9 (1)
and 42.1 (1)°, respectively.
The five membered isoxazolidine ring (C9-C1,O3,N2) adopts a twisted conformation On O3 and N2 with a pseudo-two-
fold axis passing through C11-C9 bond. The other five membered tetrahydrofuran, dioxolone and pyrrole rings adopt en-
velope conformation on C12, O6 and C8 respectively. The puckering parameters (Cremer & Pople, 1975) and the lowest
displacement asymmetry parameters (Nardelli, 1983) as follows: for the isoxazolidine ring q2 = 0.353 (1) Å, φ = 26.0 (1)°,
ΔS(N2) is 9.6 (1)° and Δ2(C9) is 7.4 (1)°, for the tetrahydrofuran ring q2 = 0.395 (1) Å, φ = 313.0 (1)°, ΔS(C12) is 6.6 (1)°
and Δ2(C15) is 11.2 (1)°, for the dioxolone ring q2 = 0.232 (1) Å, φ = 295.8 (1)°, ΔS(O6) is 5.3 (1)° and Δ2(C15) is 6.2 (1)°
and for the pyrrole ring q2 = 0.085 (1) Å, φ = 140.0 (1)°, ΔS(C8) is 0.2 (1)° and Δ2(C7) is 4.5 (1)°.
The crystal structure is stabilized by intermolecular C—H···O hydrogen bonds (Table 1; Fig. 2). The crystal structure is
further stabilized by C—H···π interactions involing rings C17—H17B···Cg1 and C21—H21···Cg2 (Cg1 and Cg2 denote the
centroid of the C1—C6 and C20—C25 phenyl rings).
Experimental
A mixture of D-glucose derived nitrone (0.5 mmol) and maleimide (0.5 mmol) was refluxed in dry toluene (10 ml) until
completion of the reaction as evidenced by TLC analysis. The solvent was evaporated under reduced pressure. The crude
product was purified by column chromatography on silica gel (Merck, 100–200 mesh, ethylacetate-petroleum ether (1:9).
Single crystals of the title compound suitable for X-ray diffraction were obtained by recrystallization from ethanol.
Refinement
All H atoms were positioned geometrically, with C—H = 0.93–0.98 Å and constrained to ride on their parent atoms, with
Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

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Figures
Fig. 1. A perspective view of the title compound with the atom-numbering scheme. Displace-
ment ellipsoids are drawn at the 30% probability level.
Fig. 2. Partial packing view, showing the C—H···O hydrogen-bonding interactions (dashed
lines), resulting in the formation of an infinite chain. H atoms not involved in the hydrogen
bonding have been omitted for clarity. [Symmetry codes: (i) x, y + 1, z; (ii) -x + 2, y - 1/2, -z +
1.]
3-(6-Benzyloxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl)- 5-(4-bromophenyl)-2-phenylperhy-
dropyrrolo[3,4-d]isoxazole-4,6-dione
Crystal data
C31H29BrN2O7
F000 = 640
Dx = 1.459 Mg m−3
Mo Kα radiation
λ = 0.71073 Å
Cell parameters from 5502 reflections
θ = 2.5–25º
µ = 1.51 mm−1
T = 293 K
Needle, colourless
Mr = 621.47
Monoclinic, P21
Hall symbol: P 2yb
a = 15.0680 (12) Å
b = 6.6801 (5) Å
c = 15.8550 (12) Å
β = 117.578 (2)º
V = 1414.57 (19) Å3
Z = 2
0.3 × 0.2 × 0.2 mm
Data collection
Bruker Kappa APEXII CCD
diffractometer
Radiation source: fine-focus sealed tube
Monochromator: graphite
T = 293 K
ω and φ scans
Absorption correction: Multi-scan
(SADABS; Bruker 2004)
Tmin = 0.734, Tmax = 0.740
20450 measured reflections
9003 independent reflections
5502 reflections with I > 2σ(I)
Rint = 0.027
θmax = 31.7º
θmin = 1.5º
h = −22→22
k = −9→8
l = −23→23

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supplementary materials
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Refinement
Refinement on F2
Hydrogen site location: inferred from neighbouring
sites
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.066P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.66 e Å−3
Δρmin = −0.38 e Å−3
Extinction correction: none
Absolute structure: Flack (1983), 3886 Friedel pairs
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.042
wR(F2) = 0.138
S = 1.00
9003 reflections
372 parameters
1 restraint
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Flack parameter: −0.001 (8)
Special details
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 mat-
rix. 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, convention-
al 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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
0.64016 (18)
0.6865
0.5464 (2)
0.5293
0.4785 (2)
0.5020 (2)
0.4553
0.5958 (2)
0.6125
0.66469 (18)
0.7771 (2)
0.85005 (18)
0.93114 (18)
0.9931
0.88614 (19)
0.9220
y
0.3845 (4)
0.4725
0.4517 (5)
0.5853
0.3213 (5)
0.1225 (5)
0.0349
0.0545 (4)
−0.0796
0.1858 (4)
−0.0588 (4)
0.2249 (4)
0.1327 (4)
0.1105
−0.0602 (4)
−0.1772
z
0.35916 (18)
0.4028
0.2949 (2)
0.2952
0.2304 (2)
0.2294 (2)
0.1858
0.2940 (2)
0.2942
0.35820 (16)
0.47898 (17)
0.45433 (17)
0.54302 (17)
0.5385
0.55592 (17)
0.5498
Uiso*/Ueq
0.0430 (6)
0.052*
0.0524 (7)
0.063*
0.0557 (7)
0.0576 (8)
0.069*
0.0462 (6)
0.055*
0.0359 (5)
0.0415 (5)
0.0381 (5)
0.0370 (5)
0.044*
0.0427 (5)
0.051*
C1
H1
C2
H2
C3
C4
H4
C5
H5
C6
C7
C8
C9
H9
C10
H10