3-(6-Benz­yloxy-2,2-dimethyl­perhydro­furo[2,3-d][1,3]dioxol-5-yl)-5-(4-bromo­phen­yl)-2-phenyl­perhydro­pyrrolo[3,4-d]isoxazole-4,6-dione

NizamMohideen, M.; Damodiran, M.; SubbiahPandi, A.; Perumal, P.T.

doi:10.1107/S1600536809015104

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1156

doi:10.1107/S1600536809015104

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3-(6-Benzyloxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl)-5-(4-bromophenyl)-2-phenylperhydropyrrolo[3,4-d]isoxazole-4,6-dione

M. NizamMohideen,^a M. Damodiran,^b A. SubbiahPandi ^c ^* and P. T. Perumal ^b

^aDepartment of Physics, The New College (Autonomous), Chennai 600 014, India, ^bOrganic Chemistry Division, Central Leather Research Institute, Chennai 600 020, India, and ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
^*Correspondence e-mail: a_spandian@yahoo.com

(Received 16 April 2009; accepted 23 April 2009; online 30 April 2009)

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⋯π 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
M_r = 621.47
Monoclinic, P 2₁
a = 15.0680 (12) Å
b = 6.6801 (5) Å
c = 15.8550 (12) Å
β = 117.578 (2)°
V = 1414.57 (19) Å³
Z = 2
Mo Kα radiation
μ = 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 ) T_min = 0.734, T_max = 0.740
20450 measured reflections
9003 independent reflections
5502 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.138
S = 1.00
9003 reflections
372 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.38 e Å⁻³
Absolute structure: Flack (1983 ), 3886 Friedel pairs
Flack parameter: −0.001 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ⁱ	0.93	2.46	3.273 (3)	145
C5—H5⋯O5ⁱⁱ	0.93	2.52	3.198 (3)	130
C9—H9⋯O1ⁱⁱ	0.98	2.58	3.418 (3)	144
C19—H19B⋯O3ⁱ	0.97	2.58	3.360 (3)	137
C17—H17b⋯Cg1ⁱⁱⁱ	0.96	2.86	3.720 (4)	150
C21—H21⋯Cg2^iv	0.93	2.67	3.559 (7)	160
Symmetry codes: (i) x, y+1, z; (ii) $[-x+2, y-{\script{1\over 2}}, -z+1]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (iv) $[-x, y-{\script{1\over 2}}, -z]$ . Cg1 and Cg2 are the centroids of the C1–C6 and C20–C25 rings, respectively.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015104/bt2932sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015104/bt2932Isup2.hkl

checkCIF report

Comment top

Isoxazolidines are potential precursors for biologically important compounds such as amino sugars (Ali et al., 1988), alkaloids (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-twofold axis passing through C11-C9 bond. The other five membered tetrahydrofuran, dioxolone and pyrrole rings adopt envelope 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)°, Δ_S(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)°, Δ_S(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)°, Δ_S(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)°, Δ_S(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).

Related literature top

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). Cg1 and Cg2 are the centroids of the C1–C6 and C20–C25 rings, respectively.

Experimental top

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.

Computing details top

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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A perspective view of the title compound with the atom-numbering scheme. Displacement 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-phenylperhydropyrrolo[3,4-d]isoxazole-4,6-dione top

Crystal data top

C₃₁H₂₉BrN₂O₇	F(000) = 640
M_r = 621.47	D_x = 1.459 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5502 reflections
a = 15.0680 (12) Å	θ = 2.5–25°
b = 6.6801 (5) Å	µ = 1.51 mm⁻¹
c = 15.8550 (12) Å	T = 293 K
β = 117.578 (2)°	Needle, colourless
V = 1414.57 (19) Å³	0.3 × 0.2 × 0.2 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	9003 independent reflections
Radiation source: fine-focus sealed tube	5502 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 31.7°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −22→22
T_min = 0.734, T_max = 0.740	k = −9→8
20450 measured reflections	l = −23→23

Refinement top

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.066P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
9003 reflections	Δρ_max = 0.66 e Å⁻³
372 parameters	Δρ_min = −0.38 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3886 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.001 (8)

Crystal data top

C₃₁H₂₉BrN₂O₇	V = 1414.57 (19) Å³
M_r = 621.47	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 15.0680 (12) Å	µ = 1.51 mm⁻¹
b = 6.6801 (5) Å	T = 293 K
c = 15.8550 (12) Å	0.3 × 0.2 × 0.2 mm
β = 117.578 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	9003 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2004)	5502 reflections with I > 2σ(I)
T_min = 0.734, T_max = 0.740	R_int = 0.027
20450 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.138	Δρ_max = 0.66 e Å⁻³
S = 1.00	Δρ_min = −0.38 e Å⁻³
9003 reflections	Absolute structure: Flack (1983), 3886 Friedel pairs
372 parameters	Absolute structure parameter: −0.001 (8)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.64016 (18)	0.3845 (4)	0.35916 (18)	0.0430 (6)
H1	0.6865	0.4725	0.4028	0.052*
C2	0.5464 (2)	0.4517 (5)	0.2949 (2)	0.0524 (7)
H2	0.5293	0.5853	0.2952	0.063*
C3	0.4785 (2)	0.3213 (5)	0.2304 (2)	0.0557 (7)
C4	0.5020 (2)	0.1225 (5)	0.2294 (2)	0.0576 (8)
H4	0.4553	0.0349	0.1858	0.069*
C5	0.5958 (2)	0.0545 (4)	0.2940 (2)	0.0462 (6)
H5	0.6125	−0.0796	0.2942	0.055*
C6	0.66469 (18)	0.1858 (4)	0.35820 (16)	0.0359 (5)
C7	0.7771 (2)	−0.0588 (4)	0.47898 (17)	0.0415 (5)
C8	0.85005 (18)	0.2249 (4)	0.45433 (17)	0.0381 (5)
C9	0.93114 (18)	0.1327 (4)	0.54302 (17)	0.0370 (5)
H9	0.9931	0.1105	0.5385	0.044*
C10	0.88614 (19)	−0.0602 (4)	0.55592 (17)	0.0427 (5)
H10	0.9220	−0.1772	0.5498	0.051*
C11	0.94837 (17)	0.2561 (3)	0.63122 (16)	0.0340 (5)
H11	0.9266	0.3948	0.6132	0.041*
C12	1.05597 (18)	0.2501 (4)	0.70747 (16)	0.0352 (5)
H12	1.0775	0.1109	0.7240	0.042*
C13	1.07749 (18)	0.3678 (3)	0.79726 (16)	0.0347 (5)
H13	1.0594	0.2926	0.8402	0.042*
C14	1.18993 (18)	0.3982 (4)	0.83916 (16)	0.0379 (5)
H14	1.2135	0.5202	0.8776	0.045*
C15	1.20853 (17)	0.3989 (4)	0.75221 (16)	0.0402 (5)
H15	1.2319	0.5306	0.7437	0.048*
C16	1.3149 (2)	0.1722 (4)	0.86285 (19)	0.0447 (6)
C17	1.3205 (3)	−0.0535 (6)	0.8586 (3)	0.0690 (9)
H17A	1.3361	−0.1092	0.9197	0.104*
H17B	1.3718	−0.0898	0.8415	0.104*
H17C	1.2572	−0.1047	0.8118	0.104*
C18	1.4135 (2)	0.2643 (7)	0.9303 (3)	0.0759 (11)
H18A	1.4063	0.4071	0.9304	0.114*
H18B	1.4629	0.2314	0.9104	0.114*
H18C	1.4342	0.2134	0.9933	0.114*
C19	0.9839 (2)	0.6190 (4)	0.82909 (19)	0.0432 (6)
H19A	0.9439	0.5111	0.8349	0.052*
H19B	0.9392	0.7302	0.7980	0.052*
C20	1.05951 (18)	0.6836 (3)	0.92725 (17)	0.0359 (5)
C21	1.0676 (2)	0.5854 (4)	1.00695 (19)	0.0453 (6)
H21	1.0286	0.4729	1.0005	0.054*
C22	1.1336 (2)	0.6541 (5)	1.0960 (2)	0.0557 (7)
H22	1.1379	0.5884	1.1495	0.067*
C23	1.1925 (2)	0.8162 (5)	1.1073 (2)	0.0600 (8)
H23	1.2366	0.8609	1.1680	0.072*
C24	1.1866 (2)	0.9139 (5)	1.0285 (2)	0.0587 (7)
H24	1.2271	1.0242	1.0356	0.070*
C25	1.1202 (2)	0.8473 (4)	0.9390 (2)	0.0471 (6)
H25	1.1162	0.9134	0.8857	0.057*
C26	0.78715 (19)	0.2237 (4)	0.63967 (16)	0.0380 (5)
C27	0.7611 (2)	0.4255 (5)	0.6230 (2)	0.0486 (6)
H27	0.8081	0.5200	0.6270	0.058*
C28	0.6640 (3)	0.4843 (6)	0.6006 (3)	0.0656 (9)
H28	0.6465	0.6187	0.5886	0.079*
C29	0.5940 (2)	0.3490 (6)	0.5957 (3)	0.0699 (10)
H29	0.5294	0.3901	0.5807	0.084*
C30	0.6209 (2)	0.1490 (6)	0.6135 (2)	0.0645 (9)
H30	0.5737	0.0551	0.6100	0.077*
C31	0.7164 (2)	0.0883 (5)	0.6361 (2)	0.0511 (7)
H31	0.7336	−0.0460	0.6492	0.061*
N1	0.76087 (15)	0.1169 (3)	0.42650 (14)	0.0342 (4)
N2	0.88766 (16)	0.1595 (3)	0.66968 (14)	0.0367 (4)
O1	0.85721 (15)	0.3700 (3)	0.41335 (14)	0.0592 (6)
O2	0.71522 (18)	−0.1839 (3)	0.46666 (16)	0.0608 (6)
O3	0.89191 (14)	−0.0499 (3)	0.64921 (12)	0.0442 (4)
O4	1.11759 (13)	0.3476 (3)	0.67218 (12)	0.0419 (4)
O5	1.28173 (14)	0.2528 (3)	0.77001 (14)	0.0501 (5)
O6	1.23964 (13)	0.2227 (3)	0.88938 (12)	0.0419 (4)
O7	1.02692 (15)	0.5529 (3)	0.77010 (13)	0.0429 (4)
Br1	0.35138 (3)	0.41736 (8)	0.14395 (3)	0.1005 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0417 (13)	0.0400 (13)	0.0428 (13)	−0.0072 (11)	0.0157 (11)	−0.0124 (11)
C2	0.0489 (15)	0.0478 (14)	0.0581 (17)	0.0043 (12)	0.0228 (13)	−0.0084 (13)
C3	0.0343 (14)	0.0731 (19)	0.0541 (18)	0.0086 (13)	0.0158 (13)	−0.0138 (14)
C4	0.0374 (14)	0.0683 (19)	0.0611 (18)	−0.0091 (13)	0.0177 (13)	−0.0319 (15)
C5	0.0384 (13)	0.0423 (12)	0.0578 (17)	−0.0065 (11)	0.0222 (12)	−0.0192 (12)
C6	0.0352 (12)	0.0398 (12)	0.0353 (12)	−0.0065 (9)	0.0185 (10)	−0.0070 (9)
C7	0.0558 (15)	0.0311 (11)	0.0400 (13)	−0.0054 (11)	0.0244 (11)	−0.0081 (10)
C8	0.0340 (12)	0.0461 (13)	0.0338 (12)	−0.0050 (10)	0.0153 (10)	−0.0001 (10)
C9	0.0329 (12)	0.0425 (12)	0.0357 (12)	0.0009 (9)	0.0161 (10)	0.0006 (10)
C10	0.0530 (14)	0.0315 (11)	0.0431 (14)	0.0070 (11)	0.0218 (11)	0.0019 (10)
C11	0.0334 (11)	0.0352 (11)	0.0328 (11)	0.0030 (9)	0.0149 (9)	0.0044 (9)
C12	0.0341 (12)	0.0363 (11)	0.0350 (12)	−0.0004 (9)	0.0158 (10)	0.0014 (9)
C13	0.0381 (12)	0.0349 (11)	0.0329 (11)	0.0004 (9)	0.0181 (10)	0.0045 (9)
C14	0.0393 (11)	0.0383 (11)	0.0316 (11)	−0.0032 (10)	0.0127 (9)	−0.0022 (10)
C15	0.0358 (11)	0.0427 (12)	0.0385 (12)	−0.0072 (10)	0.0142 (10)	0.0027 (11)
C16	0.0345 (13)	0.0587 (15)	0.0402 (13)	0.0000 (11)	0.0166 (11)	0.0047 (12)
C17	0.076 (2)	0.0624 (19)	0.080 (2)	0.0156 (18)	0.0458 (19)	0.0102 (17)
C18	0.0406 (18)	0.111 (3)	0.064 (2)	−0.0090 (18)	0.0140 (16)	−0.008 (2)
C19	0.0424 (14)	0.0470 (14)	0.0435 (14)	0.0091 (11)	0.0227 (12)	0.0013 (11)
C20	0.0380 (12)	0.0380 (12)	0.0371 (12)	0.0077 (10)	0.0219 (10)	0.0018 (10)
C21	0.0496 (15)	0.0464 (14)	0.0456 (15)	0.0005 (12)	0.0268 (13)	0.0069 (11)
C22	0.0602 (18)	0.0670 (18)	0.0401 (15)	0.0136 (15)	0.0234 (14)	0.0121 (13)
C23	0.0455 (16)	0.077 (2)	0.0481 (17)	0.0061 (15)	0.0141 (13)	−0.0170 (15)
C24	0.0553 (16)	0.0568 (16)	0.0696 (19)	−0.0134 (15)	0.0337 (14)	−0.0139 (16)
C25	0.0585 (17)	0.0401 (13)	0.0524 (16)	−0.0017 (11)	0.0338 (14)	0.0016 (11)
C26	0.0387 (13)	0.0487 (13)	0.0282 (11)	−0.0048 (10)	0.0167 (10)	−0.0032 (10)
C27	0.0428 (13)	0.0461 (14)	0.0596 (16)	0.0018 (12)	0.0259 (12)	0.0012 (13)
C28	0.0530 (19)	0.071 (2)	0.078 (2)	0.0156 (15)	0.0347 (17)	0.0065 (17)
C29	0.0366 (15)	0.108 (3)	0.067 (2)	0.0044 (16)	0.0253 (15)	−0.008 (2)
C30	0.0486 (18)	0.088 (3)	0.065 (2)	−0.0179 (17)	0.0339 (16)	−0.0119 (18)
C31	0.0508 (16)	0.0582 (16)	0.0496 (16)	−0.0155 (13)	0.0278 (13)	−0.0062 (13)
N1	0.0341 (10)	0.0343 (9)	0.0339 (10)	−0.0038 (7)	0.0155 (8)	−0.0032 (8)
N2	0.0378 (10)	0.0365 (10)	0.0355 (10)	−0.0027 (8)	0.0166 (8)	−0.0001 (8)
O1	0.0442 (10)	0.0710 (13)	0.0481 (11)	−0.0187 (9)	0.0092 (8)	0.0213 (10)
O2	0.0768 (15)	0.0417 (10)	0.0591 (13)	−0.0238 (10)	0.0274 (12)	−0.0086 (9)
O3	0.0540 (10)	0.0345 (8)	0.0416 (9)	0.0038 (8)	0.0198 (8)	0.0092 (7)
O4	0.0365 (9)	0.0575 (11)	0.0325 (8)	−0.0067 (8)	0.0167 (7)	−0.0015 (7)
O5	0.0431 (11)	0.0668 (12)	0.0457 (10)	0.0046 (9)	0.0250 (9)	0.0085 (9)
O6	0.0403 (10)	0.0494 (10)	0.0364 (9)	0.0036 (8)	0.0180 (8)	0.0072 (7)
O7	0.0575 (11)	0.0388 (9)	0.0350 (9)	0.0079 (8)	0.0235 (8)	0.0037 (7)
Br1	0.0491 (2)	0.1229 (4)	0.0909 (3)	0.0303 (2)	−0.00047 (17)	−0.0247 (3)

Geometric parameters (Å, º) top

C1—C2	1.379 (4)	C16—O6	1.421 (3)
C1—C6	1.380 (4)	C16—O5	1.423 (3)
C1—H1	0.9300	C16—C18	1.502 (4)
C2—C3	1.372 (4)	C16—C17	1.513 (5)
C2—H2	0.9300	C17—H17A	0.9600
C3—C4	1.377 (5)	C17—H17B	0.9600
C3—Br1	1.878 (3)	C17—H17C	0.9600
C4—C5	1.384 (4)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.380 (3)	C18—H18C	0.9600
C5—H5	0.9300	C19—O7	1.433 (3)
C6—N1	1.425 (3)	C19—C20	1.505 (4)
C7—O2	1.198 (3)	C19—H19A	0.9700
C7—N1	1.393 (3)	C19—H19B	0.9700
C7—C10	1.527 (4)	C20—C21	1.378 (3)
C8—O1	1.199 (3)	C20—C25	1.382 (4)
C8—N1	1.405 (3)	C21—C22	1.376 (4)
C8—C9	1.503 (3)	C21—H21	0.9300
C9—C10	1.513 (4)	C22—C23	1.359 (5)
C9—C11	1.538 (3)	C22—H22	0.9300
C9—H9	0.9800	C23—C24	1.375 (5)
C10—O3	1.443 (3)	C23—H23	0.9300
C10—H10	0.9800	C24—C25	1.377 (4)
C11—N2	1.464 (3)	C24—H24	0.9300
C11—C12	1.509 (3)	C25—H25	0.9300
C11—H11	0.9800	C26—C31	1.379 (4)
C12—O4	1.442 (3)	C26—C27	1.395 (4)
C12—C13	1.524 (3)	C26—N2	1.427 (3)
C12—H12	0.9800	C27—C28	1.392 (4)
C13—O7	1.411 (3)	C27—H27	0.9300
C13—C14	1.520 (3)	C28—C29	1.364 (5)
C13—H13	0.9800	C28—H28	0.9300
C14—O6	1.420 (3)	C29—C30	1.386 (6)
C14—C15	1.529 (3)	C29—H29	0.9300
C14—H14	0.9800	C30—C31	1.374 (4)
C15—O5	1.400 (3)	C30—H30	0.9300
C15—O4	1.413 (3)	C31—H31	0.9300
C15—H15	0.9800	N2—O3	1.444 (3)

C2—C1—C6	119.5 (2)	O6—C16—C17	108.6 (2)
C2—C1—H1	120.2	O5—C16—C17	109.3 (3)
C6—C1—H1	120.2	C18—C16—C17	112.5 (3)
C3—C2—C1	120.0 (3)	C16—C17—H17A	109.5
C3—C2—H2	120.0	C16—C17—H17B	109.5
C1—C2—H2	120.0	H17A—C17—H17B	109.5
C2—C3—C4	120.9 (3)	C16—C17—H17C	109.5
C2—C3—Br1	119.0 (2)	H17A—C17—H17C	109.5
C4—C3—Br1	120.2 (2)	H17B—C17—H17C	109.5
C3—C4—C5	119.3 (3)	C16—C18—H18A	109.5
C3—C4—H4	120.4	C16—C18—H18B	109.5
C5—C4—H4	120.4	H18A—C18—H18B	109.5
C6—C5—C4	119.9 (3)	C16—C18—H18C	109.5
C6—C5—H5	120.1	H18A—C18—H18C	109.5
C4—C5—H5	120.1	H18B—C18—H18C	109.5
C1—C6—C5	120.4 (2)	O7—C19—C20	114.1 (2)
C1—C6—N1	119.1 (2)	O7—C19—H19A	108.7
C5—C6—N1	120.5 (2)	C20—C19—H19A	108.7
O2—C7—N1	125.6 (3)	O7—C19—H19B	108.7
O2—C7—C10	126.5 (2)	C20—C19—H19B	108.7
N1—C7—C10	107.9 (2)	H19A—C19—H19B	107.6
O1—C8—N1	123.9 (2)	C21—C20—C25	118.8 (2)
O1—C8—C9	126.9 (2)	C21—C20—C19	121.0 (2)
N1—C8—C9	109.2 (2)	C25—C20—C19	120.2 (2)
C8—C9—C10	104.74 (19)	C22—C21—C20	119.8 (3)
C8—C9—C11	110.7 (2)	C22—C21—H21	120.1
C10—C9—C11	103.35 (19)	C20—C21—H21	120.1
C8—C9—H9	112.5	C23—C22—C21	121.2 (3)
C10—C9—H9	112.5	C23—C22—H22	119.4
C11—C9—H9	112.5	C21—C22—H22	119.4
O3—C10—C9	106.3 (2)	C22—C23—C24	119.7 (3)
O3—C10—C7	110.5 (2)	C22—C23—H23	120.2
C9—C10—C7	105.72 (19)	C24—C23—H23	120.2
O3—C10—H10	111.4	C25—C24—C23	119.5 (3)
C9—C10—H10	111.4	C25—C24—H24	120.2
C7—C10—H10	111.4	C23—C24—H24	120.2
N2—C11—C12	107.55 (18)	C24—C25—C20	120.9 (3)
N2—C11—C9	105.52 (19)	C24—C25—H25	119.5
C12—C11—C9	112.38 (19)	C20—C25—H25	119.5
N2—C11—H11	110.4	C31—C26—C27	118.8 (3)
C12—C11—H11	110.4	C31—C26—N2	119.8 (2)
C9—C11—H11	110.4	C27—C26—N2	121.1 (2)
O4—C12—C11	108.86 (18)	C28—C27—C26	119.5 (3)
O4—C12—C13	103.47 (18)	C28—C27—H27	120.3
C11—C12—C13	114.83 (19)	C26—C27—H27	120.3
O4—C12—H12	109.8	C29—C28—C27	121.3 (3)
C11—C12—H12	109.8	C29—C28—H28	119.3
C13—C12—H12	109.8	C27—C28—H28	119.3
O7—C13—C14	110.6 (2)	C28—C29—C30	118.8 (3)
O7—C13—C12	108.39 (18)	C28—C29—H29	120.6
C14—C13—C12	100.91 (18)	C30—C29—H29	120.6
O7—C13—H13	112.1	C31—C30—C29	120.6 (3)
C14—C13—H13	112.1	C31—C30—H30	119.7
C12—C13—H13	112.1	C29—C30—H30	119.7
O6—C14—C13	109.06 (19)	C30—C31—C26	120.9 (3)
O6—C14—C15	103.8 (2)	C30—C31—H31	119.5
C13—C14—C15	103.82 (17)	C26—C31—H31	119.5
O6—C14—H14	113.1	C7—N1—C8	111.6 (2)
C13—C14—H14	113.1	C7—N1—C6	124.2 (2)
C15—C14—H14	113.1	C8—N1—C6	124.1 (2)
O5—C15—O4	111.0 (2)	C26—N2—O3	111.51 (19)
O5—C15—C14	105.81 (19)	C26—N2—C11	120.00 (19)
O4—C15—C14	107.62 (18)	O3—N2—C11	103.42 (17)
O5—C15—H15	110.8	N2—O3—C10	106.78 (17)
O4—C15—H15	110.8	C15—O4—C12	106.98 (17)
C14—C15—H15	110.8	C15—O5—C16	109.83 (19)
O6—C16—O5	105.7 (2)	C14—O6—C16	108.42 (18)
O6—C16—C18	110.7 (2)	C13—O7—C19	114.50 (18)
O5—C16—C18	109.9 (3)

C6—C1—C2—C3	−0.2 (4)	C19—C20—C25—C24	177.0 (3)
C1—C2—C3—C4	0.7 (5)	C31—C26—C27—C28	−1.9 (4)
C1—C2—C3—Br1	179.9 (2)	N2—C26—C27—C28	−175.4 (3)
C2—C3—C4—C5	−0.5 (5)	C26—C27—C28—C29	0.9 (5)
Br1—C3—C4—C5	−179.7 (2)	C27—C28—C29—C30	−0.1 (6)
C3—C4—C5—C6	−0.3 (5)	C28—C29—C30—C31	0.3 (6)
C2—C1—C6—C5	−0.5 (4)	C29—C30—C31—C26	−1.4 (5)
C2—C1—C6—N1	−178.4 (2)	C27—C26—C31—C30	2.2 (4)
C4—C5—C6—C1	0.8 (4)	N2—C26—C31—C30	175.7 (3)
C4—C5—C6—N1	178.6 (2)	O2—C7—N1—C8	−175.9 (2)
O1—C8—C9—C10	−172.5 (3)	C10—C7—N1—C8	5.6 (3)
N1—C8—C9—C10	9.1 (3)	O2—C7—N1—C6	8.6 (4)
O1—C8—C9—C11	76.7 (3)	C10—C7—N1—C6	−169.94 (19)
N1—C8—C9—C11	−101.7 (2)	O1—C8—N1—C7	172.1 (2)
C8—C9—C10—O3	−123.0 (2)	C9—C8—N1—C7	−9.4 (3)
C11—C9—C10—O3	−7.1 (2)	O1—C8—N1—C6	−12.3 (4)
C8—C9—C10—C7	−5.5 (2)	C9—C8—N1—C6	166.1 (2)
C11—C9—C10—C7	110.4 (2)	C1—C6—N1—C7	134.2 (2)
O2—C7—C10—O3	−63.6 (3)	C5—C6—N1—C7	−43.7 (3)
N1—C7—C10—O3	114.9 (2)	C1—C6—N1—C8	−40.8 (3)
O2—C7—C10—C9	−178.2 (3)	C5—C6—N1—C8	141.3 (2)
N1—C7—C10—C9	0.3 (2)	C31—C26—N2—O3	27.9 (3)
C8—C9—C11—N2	95.2 (2)	C27—C26—N2—O3	−158.7 (2)
C10—C9—C11—N2	−16.4 (2)	C31—C26—N2—C11	149.0 (2)
C8—C9—C11—C12	−147.9 (2)	C27—C26—N2—C11	−37.7 (3)
C10—C9—C11—C12	100.5 (2)	C12—C11—N2—C26	148.6 (2)
N2—C11—C12—O4	−179.02 (17)	C9—C11—N2—C26	−91.2 (2)
C9—C11—C12—O4	65.3 (2)	C12—C11—N2—O3	−86.4 (2)
N2—C11—C12—C13	−63.6 (2)	C9—C11—N2—O3	33.8 (2)
C9—C11—C12—C13	−179.3 (2)	C26—N2—O3—C10	91.0 (2)
O4—C12—C13—O7	75.3 (2)	C11—N2—O3—C10	−39.3 (2)
C11—C12—C13—O7	−43.2 (3)	C9—C10—O3—N2	28.7 (2)
O4—C12—C13—C14	−40.9 (2)	C7—C10—O3—N2	−85.5 (2)
C11—C12—C13—C14	−159.34 (19)	O5—C15—O4—C12	95.9 (2)
O7—C13—C14—O6	163.81 (18)	C14—C15—O4—C12	−19.5 (3)
C12—C13—C14—O6	−81.6 (2)	C11—C12—O4—C15	160.8 (2)
O7—C13—C14—C15	−86.0 (2)	C13—C12—O4—C15	38.2 (2)
C12—C13—C14—C15	28.5 (2)	O4—C15—O5—C16	−120.5 (2)
O6—C14—C15—O5	−11.6 (2)	C14—C15—O5—C16	−4.1 (3)
C13—C14—C15—O5	−125.6 (2)	O6—C16—O5—C15	18.4 (3)
O6—C14—C15—O4	107.1 (2)	C18—C16—O5—C15	−101.0 (3)
C13—C14—C15—O4	−6.9 (3)	C17—C16—O5—C15	135.0 (3)
O7—C19—C20—C21	−118.0 (3)	C13—C14—O6—C16	133.4 (2)
O7—C19—C20—C25	64.0 (3)	C15—C14—O6—C16	23.3 (2)
C25—C20—C21—C22	1.6 (4)	O5—C16—O6—C14	−26.3 (3)
C19—C20—C21—C22	−176.4 (2)	C18—C16—O6—C14	92.6 (3)
C20—C21—C22—C23	−1.0 (4)	C17—C16—O6—C14	−143.4 (2)
C21—C22—C23—C24	−0.1 (5)	C14—C13—O7—C19	−109.0 (2)
C22—C23—C24—C25	0.6 (5)	C12—C13—O7—C19	141.2 (2)
C23—C24—C25—C20	0.0 (4)	C20—C19—O7—C13	70.5 (3)
C21—C20—C25—C24	−1.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	0.93	2.46	3.273 (3)	145
C5—H5···O5ⁱⁱ	0.93	2.52	3.198 (3)	130
C9—H9···O1ⁱⁱ	0.98	2.58	3.418 (3)	144
C19—H19B···O3ⁱ	0.97	2.58	3.360 (3)	137
C17—H17b···Cg1ⁱⁱⁱ	0.96	2.86	3.720 (4)	150
C21—H21···Cg2^iv	0.93	2.67	3.559 (7)	160

Symmetry codes: (i) x, y+1, z; (ii) −x+2, y−1/2, −z+1; (iii) −x, y−1/2, −z+1; (iv) −x, y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₃₁H₂₉BrN₂O₇
M_r	621.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	15.0680 (12), 6.6801 (5), 15.8550 (12)
β (°)	117.578 (2)
V (Å³)	1414.57 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2004)
T_min, T_max	0.734, 0.740
No. of measured, independent and observed [I > 2σ(I)] reflections	20450, 9003, 5502
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.738

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.138, 1.00
No. of reflections	9003
No. of parameters	372
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.38
Absolute structure	Flack (1983), 3886 Friedel pairs
Absolute structure parameter	−0.001 (8)

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	0.93	2.46	3.273 (3)	145.4
C5—H5···O5ⁱⁱ	0.93	2.52	3.198 (3)	130.4
C9—H9···O1ⁱⁱ	0.98	2.58	3.418 (3)	143.5
C19—H19B···O3ⁱ	0.97	2.58	3.360 (3)	137.2
C17—H17b···Cg1ⁱⁱⁱ	0.96	2.86	3.720 (4)	150
C21—H21···Cg2^iv	0.93	2.67	3.559 (7)	160

Symmetry codes: (i) x, y+1, z; (ii) −x+2, y−1/2, −z+1; (iii) −x, y−1/2, −z+1; (iv) −x, y−1/2, −z.

Acknowledgements

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.

References

Ali, A. S., Khan, J. H. & Wazeer, M. I. M. (1988). Tetrahedron, 44, 5911–5920. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Goti, A., Fedi, V., Naneli, L., De Sarlo, F. & Brandi, A. (1997). Synlett, pp. 577-579. CrossRef Google Scholar
Huisgen, R. (1984). 1,3-Dipolar Cycloaddition Chemistry, Vol. I, edited by A. Padawa, pp. 3–27. New York: Wiley Interscience. Google Scholar
Kumar, K. R. R., Mallesha, H. & Rangappa, K. S. (2003). Synth. Commun. 33, 1545–1555. Web of Science CrossRef CAS Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-(6-Benz­yl­oxy-2,2-di­methyl­perhydro­furo[2,3-d][1,3]dioxol-5-yl)-5-(4-bromo­phen­yl)-2-phenyl­perhydro­pyrrolo[3,4-d]isoxazole-4,6-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(6-Benzyloxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl)-5-(4-bromophenyl)-2-phenylperhydropyrrolo[3,4-d]isoxazole-4,6-dione