(3R,4S)-3,4-Isopropylidenedioxy-5-phenylsulfonylmethyl-3,4-dihydro-2H-pyrrole 1-oxide

Flores, M.F.; Garcia, P.; Garrido, N.M.; Sanz, F.; Diez, D.

doi:10.1107/S1600536811010737

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1115

doi:10.1107/S1600536811010737

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(3R,4S)-3,4-Isopropylidenedioxy-5-phenylsulfonylmethyl-3,4-dihydro-2H-pyrrole 1-oxide

Mari Fe Flores,^a P. Garcia,^a Narciso M. Garrido,^a Francisca Sanz ^b and David Diez ^a ^*

^aDepartamento de Quimica Organica, Universidad de Salamanca, Plaza de los Caidos, 37008-Salamanca. Spain, and ^bServicio General de Rayos X, Universidad de Salamanca, Plaza de los Caidos, 37008-Salamanca. Spain
^*Correspondence e-mail: ddm@usal.es

(Received 17 March 2011; accepted 22 March 2011; online 13 April 2011)

The title compound, C₁₄H₁₇NO₅S, was prepared by oxidation of (2R,3S,4R)-2-phenylsulfonylmethyl-1-hydroxy-3,4-isopropylidenedioxypyrrolidine. Its crystal structure confirms unequivocally its configuration. Two intermolecular C—H⋯O interactions help to establish the packing.

Related literature

For the preparation, see: Flores et al. (2010 ). For the standard oxidation of hydroxylamines to nitrones with manganese dioxide, see: Cicchi et al. (2001 ). For background to organocatalysts, see: Berkessel & Groger (2005 ); Macmillan (2008 ). For analogues of the organocatalyst L-proline, see: Andrey et al. (2004 ); Cobb et al. (2004 ); Tanaka et al. (2004 ); Wang et al. (2005 ).

Experimental

Crystal data

C₁₄H₁₇NO₅S
M_r = 311.35
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.6424 (2) Å
b = 15.5592 (7) Å
c = 16.9097 (8) Å
V = 1484.52 (11) Å³
Z = 4
Cu Kα radiation
μ = 2.14 mm⁻¹
T = 298 K
0.10 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.815, T_max = 0.880
8018 measured reflections
2487 independent reflections
2159 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.084
S = 1.06
2487 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack (1983 ),
Flack parameter: 0.06 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O4ⁱ	0.98	2.50	3.389 (2)	151
C12—H12⋯O3ⁱⁱ	0.93	2.51	3.270 (4)	139
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker 2006); cell refinement: SAINT (Bruker 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010737/bt5495sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010737/bt5495Isup2.hkl

checkCIF report

Comment top

Recently there has been an enormous interest in organocatalysis (Berkessel & Groger et al. 2005 and Macmillan, 2008). Among the many known organocatalysts L-proline is perhaps the one which has been most studied. This fact has led to the appearance of many analogues (Andrey et al., 2004; Wang et al., 2005; Cobb et al., 2004; Tanaka et al., 2004). In our research group we have developed new organocatalyst using nitrones as starting material (Flores et al., 2010). This catalyst was obtained from chiral hydroxylamine (I) (Fig. 1). Here we communicate the oxidation of this compound into nitrone II and the crystal structure determination.

The crystal contains an unique molecule in the asymmetric unit (Fig. 2). The title molecule consists of a pyrroline-N-oxide ring with a phenylsulfonylmethylgroup and an isopropylidenedioxy group as susbtituents. All the bond lengths and angles are within the normal ranges. Statistically no diference is observed between the S1—O4 = 1.4310 (19) Å and S1—O5 = 1.4334 (18) Å distances suggesting that the two oxygen are very similar. The S1—C8 and S1—C9 bond lengths are 1.784 (2) Å and 1.755 (3) Å, respectively. The C—S—C and O—S—O angles are 104.02 (12)° and 119.46 (14)°, respectively. The large O—S—O angle and this deviation from the optimal 109.5° angle can be explained by the repulsion of the lone pairs of the oxygen placing the oxygen atoms as far away from each other as possible and thus minimizing the C—S—C angle. The molecule is twisted at the C—S bond being the C2—C8—S1—C9 torsion angle of -59.4 (7)°. The carbonyl group at atom N1 is desviated from the planar conformation with the pyrroline ring being the O3—N1—C3—C4 torsion angle of 165.9 (5)°.

Crystal packing (Fig. 3) is stabilized by two intermolecular C-H···O interactions. One occurs between the carbon atom (C4) of the isopropylidenedioxypyrroline group and the oxygen atom (O4) of the phenylsufonylmethyl group of the neighboring molecule oriented in the opposite direction along c axis with d(C4-H4···O4) = 3.389 (2) Å and <C4-H4···O4> = 151°. This leads to infinite molecular chains running along the [001] direction, which are joined each other along the b axis by another intermolecular interaction between the oxygen atom (O3) of the pyrroline group and the carbon atom (C12) of the phenyl group of the next molecule with d(C12-H3···O3) = 3.270 (1) Å and <C12-H3···O3> = 139°.

Related literature top

For the preparation, see: Flores et al. (2010). For the standard oxidation of hydroxylamines to nitrones with manganese dioxide, see: Cicchi et al. (2001). For background to organocatalysts, see: Berkessel & Groger (2005); Macmillan (2008). For analogues of the organocatalyst L-proline, see: Andrey et al. (2004); Cobb et al. (2004); Tanaka et al. (2004); Wang et al. (2005).

Experimental top

The title N-oxide, (II), was obtained by spontaneous oxidation of (2R,3S,4R)-2-Phenylsulfonylmethyl-1-hydroxy-3,4-isopropylidenedioxypyrrolidine (I) (Flores et al. 2010) in a 30% of yield. Our attention was then turned to the synthesis of this nitrone because of the important role nitrones play in organic syntheses, particularly in the field of alkaloids, nitrogen containing natural products or bioactive analogues. Taking this into account we tried the standard oxidation of hydroxylamines to nitrones with manganese dioxide according to the methodology described by Cicchi et al. (2001). MnO₂ (107.2 mg, 1.11 mmol) was added to a solution of hydroxylamine I (234 mg, 0.74 mmol) in DCM (1.5 ml) at 0° C. The resulting mixture was stirred for 2 h, then it was filtered through celite; and concentrated. The resulting crude residue was purified by flash chromatography (silica gel, hexane/ EtAcO 1:1) to obtain the nitrone II (229 mg, 98%) (Flores et al., 2010). Well shaped colourless single crystals were obtained by crystallization from EtOAc/Et₂O. [α]_D²⁰ = +110.7 (c = 1.17, CHCl₃). IR (film): 3376 (broad), 3058, 2995, 2967, 1580 cm^{-1. 1}H NMR (200 MHz, CDCl₃, δ p.p.m.): 7.94 (2H, m, Horto), 7.69–7.58 (3H, m, Hmeta Hpara), 5.58 (1H, d, J = 6.2 Hz, H-4), 4.87 (1H, t, J = 6.2 and 12 Hz H-3), 4.04 (2H, d, J = 4.4 Hz, H-2), 3.96 (2H, s, 2H-1) 1.38 (3H, s, Me-acetonide), 1.37 (3H, s, Me-acetonide). ¹³C NMR (50 MHz, CDCl₃, δ p.p.m.): 139.7 (C—Ar), 134.62 (CH-para), 134.0 (C-5), 129.6 (2CH-meta), 128.1 (2CH-orto), 112.6 (C-acetonide), 80.8 (CH-4), 71.7 (CH-3), 68.1 (CH2–2), 52.1 (CH2–1), 27.2 (Me-acetonide), 25.8 (Me-acetonide). HRMS (EI): C₁₄H₁₇NO₅S requires (M+Na)⁺, 334.0725, found 334.0703.

Computing details top

Data collection: APEX2 (Bruker 2006); cell refinement: SAINT (Bruker 2006); data reduction: SAINT (Bruker 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Reaction scheme.
	Fig. 2. Molecular structure of C₁₄H₁₇NO₅S. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 3. Crystal packing of C₁₄H₁₇NO₅S view along a axis, showing intermolecular hydrogen bonding.

(3R,4S)-3,4-Isopropylidenedioxy-5-phenylsulfonylmethyl- 3,4-dihydro-2H-pyrrole 1-oxide top

Crystal data top

C₁₄H₁₇NO₅S	F(000) = 656
M_r = 311.35	D_x = 1.393 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1922 reflections
a = 5.6424 (2) Å	θ = 3.9–55.3°
b = 15.5592 (7) Å	µ = 2.14 mm⁻¹
c = 16.9097 (8) Å	T = 298 K
V = 1484.52 (11) Å³	Prismatic, colourless
Z = 4	0.10 × 0.08 × 0.06 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2487 independent reflections
Radiation source: fine-focus sealed tube	2159 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
phi and ω scans	θ_max = 67.5°, θ_min = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −6→5
T_min = 0.815, T_max = 0.880	k = −18→15
8018 measured reflections	l = −18→19

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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0335P)² + 0.1514P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2487 reflections	Δρ_max = 0.14 e Å⁻³
192 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 907 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (2)

Crystal data top

C₁₄H₁₇NO₅S	V = 1484.52 (11) Å³
M_r = 311.35	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 5.6424 (2) Å	µ = 2.14 mm⁻¹
b = 15.5592 (7) Å	T = 298 K
c = 16.9097 (8) Å	0.10 × 0.08 × 0.06 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2487 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	2159 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.880	R_int = 0.030
8018 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.084	Δρ_max = 0.14 e Å⁻³
S = 1.06	Δρ_min = −0.15 e Å⁻³
2487 reflections	Absolute structure: Flack (1983), 907 Friedel pairs
192 parameters	Absolute structure parameter: 0.06 (2)
0 restraints

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
S1	0.89076 (11)	0.02630 (4)	0.36234 (4)	0.05643 (18)
O1	0.8060 (3)	0.16596 (13)	0.57625 (11)	0.0614 (5)
O2	0.9722 (5)	0.10911 (14)	0.68680 (13)	0.0894 (7)
O3	1.3072 (4)	−0.05736 (13)	0.53437 (13)	0.0813 (6)
O4	0.9927 (4)	0.05353 (13)	0.28901 (11)	0.0739 (6)
O5	0.6496 (3)	0.04808 (13)	0.37996 (14)	0.0738 (6)
N1	1.1197 (4)	−0.01709 (14)	0.55737 (13)	0.0619 (6)
C1	0.8010 (4)	0.07555 (18)	0.56728 (16)	0.0587 (7)
H1	0.6470	0.0557	0.5477	0.070*
C2	0.9998 (4)	0.04067 (16)	0.51895 (15)	0.0521 (6)
C3	1.0217 (6)	−0.03387 (19)	0.63738 (19)	0.0805 (8)
H3A	1.1460	−0.0341	0.6770	0.097*
H3B	0.9384	−0.0884	0.6390	0.097*
C4	0.8538 (5)	0.0402 (2)	0.64986 (17)	0.0729 (8)
H4	0.7099	0.0231	0.6782	0.088*
C5	0.9533 (4)	0.18574 (16)	0.64286 (17)	0.0549 (6)
C6	1.1963 (5)	0.2119 (3)	0.6143 (2)	0.0922 (11)
H6A	1.2918	0.2289	0.6586	0.138*
H6B	1.1819	0.2592	0.5782	0.138*
H6C	1.2698	0.1642	0.5878	0.138*
C7	0.8367 (6)	0.2541 (2)	0.6910 (2)	0.0864 (10)
H7A	0.6857	0.2338	0.7094	0.130*
H7B	0.8143	0.3045	0.6591	0.130*
H7C	0.9351	0.2680	0.7355	0.130*
C8	1.0714 (4)	0.06909 (17)	0.43949 (14)	0.0520 (6)
H8A	1.2345	0.0520	0.4304	0.062*
H8B	1.0648	0.1313	0.4374	0.062*
C9	0.9226 (4)	−0.08537 (16)	0.37208 (15)	0.0523 (6)
C10	1.1198 (5)	−0.12509 (19)	0.33956 (16)	0.0653 (7)
H10	1.2338	−0.0933	0.3127	0.078*
C11	1.1429 (5)	−0.2125 (2)	0.3480 (2)	0.0754 (9)
H11	1.2732	−0.2400	0.3257	0.090*
C12	0.9786 (6)	−0.26022 (19)	0.38851 (18)	0.0705 (8)
H12	0.9981	−0.3193	0.3941	0.085*
C13	0.7836 (5)	−0.21963 (19)	0.42093 (19)	0.0703 (8)
H13	0.6707	−0.2516	0.4481	0.084*
C14	0.7551 (4)	−0.13237 (18)	0.41327 (17)	0.0609 (7)
H14	0.6245	−0.1051	0.4356	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0530 (3)	0.0692 (4)	0.0471 (3)	−0.0058 (3)	−0.0062 (3)	0.0034 (3)
O1	0.0476 (9)	0.0863 (13)	0.0503 (11)	0.0057 (8)	−0.0094 (9)	0.0002 (9)
O2	0.1365 (19)	0.0753 (12)	0.0565 (12)	−0.0047 (13)	−0.0356 (13)	0.0064 (10)
O3	0.0906 (14)	0.0759 (13)	0.0774 (15)	0.0194 (11)	0.0000 (12)	0.0008 (11)
O4	0.0948 (13)	0.0849 (13)	0.0421 (11)	−0.0213 (11)	−0.0065 (11)	0.0110 (9)
O5	0.0455 (9)	0.0819 (13)	0.0939 (16)	0.0066 (8)	−0.0109 (10)	−0.0017 (11)
N1	0.0731 (13)	0.0599 (12)	0.0528 (13)	−0.0067 (12)	0.0011 (13)	0.0040 (11)
C1	0.0440 (13)	0.0819 (18)	0.0503 (16)	−0.0131 (12)	0.0022 (12)	−0.0013 (14)
C2	0.0494 (12)	0.0638 (15)	0.0431 (13)	−0.0127 (12)	−0.0020 (12)	0.0028 (12)
C3	0.116 (2)	0.0678 (17)	0.0573 (17)	−0.0182 (17)	0.0092 (19)	0.0161 (16)
C4	0.0835 (18)	0.087 (2)	0.0485 (15)	−0.0228 (16)	0.0111 (16)	0.0062 (15)
C5	0.0470 (12)	0.0704 (15)	0.0471 (14)	0.0057 (11)	−0.0093 (13)	0.0006 (13)
C6	0.0543 (16)	0.135 (3)	0.087 (3)	−0.0178 (17)	−0.0027 (17)	−0.017 (2)
C7	0.077 (2)	0.117 (3)	0.065 (2)	0.0361 (18)	−0.0159 (17)	−0.0214 (19)
C8	0.0454 (13)	0.0655 (14)	0.0451 (14)	−0.0080 (11)	0.0019 (12)	0.0038 (11)
C9	0.0469 (13)	0.0682 (14)	0.0418 (14)	−0.0061 (11)	0.0018 (12)	−0.0013 (11)
C10	0.0524 (14)	0.0823 (18)	0.0612 (17)	−0.0056 (14)	0.0119 (15)	0.0050 (14)
C11	0.0662 (17)	0.0833 (19)	0.077 (2)	0.0129 (15)	0.0121 (18)	−0.0042 (16)
C12	0.0748 (18)	0.0687 (16)	0.068 (2)	−0.0018 (14)	−0.0025 (17)	0.0036 (15)
C13	0.0686 (17)	0.080 (2)	0.062 (2)	−0.0203 (15)	0.0052 (17)	0.0047 (15)
C14	0.0471 (13)	0.0774 (18)	0.0581 (18)	−0.0093 (13)	0.0092 (14)	−0.0027 (14)

Geometric parameters (Å, º) top

S1—O4	1.4310 (19)	C5—C6	1.510 (4)
S1—O5	1.4334 (18)	C6—H6A	0.9600
S1—C9	1.755 (3)	C6—H6B	0.9600
S1—C8	1.784 (2)	C6—H6C	0.9600
O1—C1	1.415 (3)	C7—H7A	0.9600
O1—C5	1.433 (3)	C7—H7B	0.9600
O2—C5	1.409 (3)	C7—H7C	0.9600
O2—C4	1.409 (4)	C8—H8A	0.9700
O3—N1	1.290 (3)	C8—H8B	0.9700
N1—C2	1.299 (3)	C9—C14	1.383 (3)
N1—C3	1.485 (4)	C9—C10	1.387 (3)
C1—C2	1.490 (4)	C10—C11	1.374 (4)
C1—C4	1.530 (4)	C10—H10	0.9300
C1—H1	0.9800	C11—C12	1.371 (4)
C2—C8	1.471 (3)	C11—H11	0.9300
C3—C4	1.506 (5)	C12—C13	1.382 (4)
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700	C13—C14	1.373 (4)
C4—H4	0.9800	C13—H13	0.9300
C5—C7	1.492 (4)	C14—H14	0.9300

O4—S1—O5	119.46 (14)	C7—C5—C6	112.5 (3)
O4—S1—C9	109.47 (13)	C5—C6—H6A	109.5
O5—S1—C9	108.16 (12)	C5—C6—H6B	109.5
O4—S1—C8	107.06 (11)	H6A—C6—H6B	109.5
O5—S1—C8	107.58 (13)	C5—C6—H6C	109.5
C9—S1—C8	104.02 (12)	H6A—C6—H6C	109.5
C1—O1—C5	108.01 (19)	H6B—C6—H6C	109.5
C5—O2—C4	112.0 (2)	C5—C7—H7A	109.5
O3—N1—C2	127.8 (2)	C5—C7—H7B	109.5
O3—N1—C3	119.7 (2)	H7A—C7—H7B	109.5
C2—N1—C3	112.5 (2)	C5—C7—H7C	109.5
O1—C1—C2	113.9 (2)	H7A—C7—H7C	109.5
O1—C1—C4	104.8 (2)	H7B—C7—H7C	109.5
C2—C1—C4	102.9 (2)	C2—C8—S1	113.50 (17)
O1—C1—H1	111.6	C2—C8—H8A	108.9
C2—C1—H1	111.6	S1—C8—H8A	108.9
C4—C1—H1	111.6	C2—C8—H8B	108.9
N1—C2—C8	121.4 (2)	S1—C8—H8B	108.9
N1—C2—C1	111.7 (2)	H8A—C8—H8B	107.7
C8—C2—C1	126.8 (2)	C14—C9—C10	120.8 (3)
N1—C3—C4	103.1 (2)	C14—C9—S1	120.1 (2)
N1—C3—H3A	111.1	C10—C9—S1	119.10 (19)
C4—C3—H3A	111.1	C11—C10—C9	118.4 (3)
N1—C3—H3B	111.1	C11—C10—H10	120.8
C4—C3—H3B	111.1	C9—C10—H10	120.8
H3A—C3—H3B	109.1	C12—C11—C10	121.6 (3)
O2—C4—C3	110.3 (3)	C12—C11—H11	119.2
O2—C4—C1	102.9 (2)	C10—C11—H11	119.2
C3—C4—C1	105.6 (2)	C11—C12—C13	119.3 (3)
O2—C4—H4	112.5	C11—C12—H12	120.4
C3—C4—H4	112.5	C13—C12—H12	120.4
C1—C4—H4	112.5	C14—C13—C12	120.5 (3)
O2—C5—O1	106.07 (19)	C14—C13—H13	119.8
O2—C5—C7	110.4 (3)	C12—C13—H13	119.8
O1—C5—C7	109.1 (2)	C13—C14—C9	119.4 (3)
O2—C5—C6	109.1 (2)	C13—C14—H14	120.3
O1—C5—C6	109.4 (2)	C9—C14—H14	120.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.98	2.50	3.389 (2)	151
C12—H12···O3ⁱⁱ	0.93	2.51	3.270 (4)	139

Symmetry codes: (i) −x+3/2, −y, z+1/2; (ii) x−1/2, −y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇NO₅S
M_r	311.35
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	5.6424 (2), 15.5592 (7), 16.9097 (8)
V (Å³)	1484.52 (11)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.14
Crystal size (mm)	0.10 × 0.08 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.815, 0.880
No. of measured, independent and observed [I > 2σ(I)] reflections	8018, 2487, 2159
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.084, 1.06
No. of reflections	2487
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15
Absolute structure	Flack (1983), 907 Friedel pairs
Absolute structure parameter	0.06 (2)

Computer programs: APEX2 (Bruker 2006), SAINT (Bruker 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.98	2.50	3.389 (2)	151
C12—H12···O3ⁱⁱ	0.93	2.51	3.270 (4)	139

Symmetry codes: (i) −x+3/2, −y, z+1/2; (ii) x−1/2, −y−1/2, −z+1.

Acknowledgements

The authors are grateful to the MICINN (CTQ2009–1172), Junta de Castilla y Leon for financial support (GR178 and SA001A09) and for the doctoral fellowships awarded to MFF.

References

Andrey, O., Alexakis, A., Tomassini, A. & Bernardinelli, G. (2004). Adv. Synth. Catal. 346, 1147–1168. Web of Science CrossRef CAS Google Scholar
Berkessel, A. & Groger, H. (2005). Asymmetric Organocatalysis. From Biomimetic Concepts to Applications in Asymmetric Synthesis. Weinheim: Wiley-VCH. Google Scholar
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 67| Part 5| May 2011| Page o1115

doi:10.1107/S1600536811010737

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

(3R,4S)-3,4-Iso­propyl­idene­dioxy-5-phenylsulfonylmethyl-3,4-di­hydro-2H-pyrrole 1-oxide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3R,4S)-3,4-Isopropylidenedioxy-5-phenylsulfonylmethyl-3,4-dihydro-2H-pyrrole 1-oxide