(7aS)-(–)-Dimeth­yl(1-oxido-3-oxo-5,6,7,7a-tetra­hydro-3H-pyrrolizin-2-yl)sulfonium

Gutiérrez-Lazcano, L.; Terán, J.L.; Juárez, J.R.; Flores-Alamo, M.; Mendoza, A.

doi:10.1107/S1600536812003601

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o752

doi:10.1107/S1600536812003601

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(7aS)-(–)-Dimethyl(1-oxido-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)sulfonium

Leonardo Gutiérrez-Lazcano,^a Joel L. Terán,^a Jorge R. Juárez,^a Marcos Flores-Alamo ^b and Angel Mendoza ^a ^*

^aCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Puebla, Pue., Mexico, and ^bFacultad de Química, Universidad Nacional Autónoma de México, 04510 México, DF, Mexico
^*Correspondence e-mail: angel.mendoza.m@gmail.com

(Received 18 January 2012; accepted 27 January 2012; online 17 February 2012)

In the zwitterionic title compound, C₉H₁₃NO₂S, the pyrrolidine heterocycle adopts an envelope conformation (with the C atom in the 7-position as the flap). The negative charge is delocalized over the two carbonyl groups and the C atom connecting them. The positive charge is located on the S atom. Two intermolecular C—H⋯O interactions are observed. The molecular geometry at the S atom is trigonal pyramidal.

Related literature

For background to the synthesis of chiral non-racemic zwitterionic compounds, see: Zang et al. (2008 ); Kappe et al. (1983 ); Palillero et al. (2009 ). For the biological activity of related structures, see: Basco et al. (1994 ); Koruznjak et al. (2003 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₉H₁₃NO₂S
M_r = 199.26
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.8761 (3) Å
b = 9.0858 (5) Å
c = 17.7107 (9) Å
V = 945.56 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 130 K
0.46 × 0.33 × 0.07 mm

Data collection

Oxford Xcalibur Atlas Gemini diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.895, T_max = 0.976
6356 measured reflections
1873 independent reflections
1736 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.065
S = 1.04
1873 reflections
120 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), with 758 Friedel pairs
Flack parameter: −0.07 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	1.00	2.55	3.4145 (19)	145
C7—H7B⋯O1ⁱⁱ	0.99	2.59	3.570 (2)	173
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2002 $[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812003601/bt5793sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003601/bt5793Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812003601/bt5793Isup3.cml

checkCIF report

Comment top

The synthesis of chiral non racemic zwitterionic compounds is an original area of interest in organic chemistry (Zang et al., 2008; Kappe et al., 1983) because they are useful intermediates for the synthesis of diverse interesting nitrogen heterocyclic compounds (Palillero et al., 2009) with interesting biological properties (Basco et al., 1994; Koruznjak et al., 2003).

In the title zwitterionic compound, C₁₉H₁₃NO₂S, the chiral centre shows an S configuration, and the five membered pyrrolidine heterocycle shows an envelope conformations on C5 with puckering parameters (Cremer & Pople, 1975) ϕ₂ = 258.4 (3)° and q₂ = 0.4038 (19) Å. The five membered ring N1/C1/C2/C3/C4 shows a twist conformation on N1—C1 with puckering parameters ϕ₂ = 0.0903 (18)° and q₂ = 22.4 (12) Å. The bond distances of C1—O2 [1.235 (2) Å] and C3—O1 [1.238 (2) Å] are similar as in related systems which were previously reported. The C2—C3 bond distance [1.406 (2) Å] has the same length as an aromatic bond and C2—C1 [1.435 (2) Å] is shorter than a typical sp³—sp³ bond distance. This suggests, that the negative charge is delocalized on the O1/C3/C2/C2/O2 system. Two intermolecular weak interactions C4—H4···O2 (3.412 (2) Å) and C7—H7B···O1 (3.570 (2) Å) are observed.

Related literature top

For background to the synthesis of chiral non-racemic zwitterionic compounds, see: Zang et al. (2008); Kappe et al. (1983); Palillero et al. (2009). For the biological activity of related structures, see: Basco et al. (1994); Koruznjak et al. (2003). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound, was obtained by an intramolecular cyclization reaction of (S)-(-)-[2-(2-Methoxycarbonyl-pyrrolidin-1-yl)-2-oxo-ethyl]-dimethyl-sulfonium; bromide (1 mmol), which was dissolved in CH₃CN (10 ml), treated with KOH (1.2 mmol) and stirred for 2 h at room temperature. The resulting mixture was concentrated in vacuum and dissolved in ethyl acetate, filtered and concentrated giving the desired compound in 98%. Crystals were obtained from an ethyl acetate/diethyl ether solution; m.p. 110–112 °C, [α]_D= -13.4 (c 1.0, CH₂Cl₂). IR (KBr) 3447, 1655, 1591, 1372 cm^{-1. 1}H NMR (400 MHz, CDCl₃) d(p.p.m., JHz): 1.51 (m, 1H), 2.05 (m, 3H), 2.99 (s, 3H), 3.01 (s, 3H), 3.12 (m, 1H), 3.57 (td, J = 7.8, 11.0 Hz, 1H), 3.85 (dd, J = 7.24, 9.28 Hz, 1H). HRMS (FAB+): Calcd for C₉H₁₃NO₂S: 199.0667. Found: 199.0665.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2002); cell refinement: CrysAlis PRO (Oxford Diffraction, 2002); data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.

(7aS)-(–)-Dimethyl(1-oxido-3-oxo-5,6,7,7a-tetrahydro-3H- pyrrolizin-2-yl)sulfonium top

Crystal data top

C₉H₁₃NO₂S	D_x = 1.406 Mg m⁻³
M_r = 199.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 4129 reflections
a = 5.8761 (3) Å	θ = 3.5–26.0°
b = 9.0858 (5) Å	µ = 0.31 mm⁻¹
c = 17.7107 (9) Å	T = 130 K
V = 945.56 (9) Å³	Plate, colourless
Z = 4	0.46 × 0.33 × 0.07 mm
F(000) = 424

Data collection top

Oxford Xcalibur Atlas Gemini diffractometer	1873 independent reflections
Graphite monochromator	1736 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm^-1	R_int = 0.037
ω scans	θ_max = 26.1°, θ_min = 3.7°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2002)	h = −7→7
T_min = 0.895, T_max = 0.976	k = −10→11
6356 measured reflections	l = −18→21

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)] = 0.027	H-atom parameters constrained
wR(F²) = 0.065	w = 1/[σ²(F_o²) + (0.0385P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
1873 reflections	Δρ_max = 0.20 e Å⁻³
120 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Absolute structure: Flack (1983), with 758 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.07 (7)

Crystal data top

C₉H₁₃NO₂S	V = 945.56 (9) Å³
M_r = 199.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.8761 (3) Å	µ = 0.31 mm⁻¹
b = 9.0858 (5) Å	T = 130 K
c = 17.7107 (9) Å	0.46 × 0.33 × 0.07 mm

Data collection top

Oxford Xcalibur Atlas Gemini diffractometer	1873 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2002)	1736 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.976	R_int = 0.037
6356 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.065	Δρ_max = 0.20 e Å⁻³
S = 1.04	Δρ_min = −0.26 e Å⁻³
1873 reflections	Absolute structure: Flack (1983), with 758 Friedel pairs
120 parameters	Absolute structure parameter: −0.07 (7)
0 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.72287 (7)	0.59085 (4)	0.01093 (2)	0.01852 (12)
O1	0.6977 (3)	0.26576 (13)	0.09183 (7)	0.0293 (3)
O2	0.4048 (2)	0.74463 (12)	0.13031 (6)	0.0229 (3)
N1	0.4198 (2)	0.53624 (15)	0.20467 (8)	0.0172 (3)
C1	0.4721 (3)	0.61719 (18)	0.14100 (9)	0.0172 (4)
C2	0.6056 (3)	0.52340 (19)	0.09255 (9)	0.0188 (4)
C3	0.6092 (3)	0.37738 (18)	0.11921 (10)	0.0193 (4)
C4	0.4806 (3)	0.38002 (17)	0.19391 (9)	0.0173 (4)
H4	0.5823	0.3464	0.2358	0.021*
C5	0.2519 (3)	0.30179 (17)	0.19885 (10)	0.0216 (4)
H5A	0.2702	0.1975	0.2138	0.026*
H5B	0.1682	0.3069	0.1504	0.026*
C6	0.1329 (3)	0.3908 (2)	0.26032 (10)	0.0228 (4)
H6A	0.1871	0.3614	0.3111	0.027*
H6B	−0.0341	0.3772	0.2579	0.027*
C7	0.1984 (3)	0.55113 (19)	0.24287 (10)	0.0222 (4)
H7A	0.0847	0.5982	0.2094	0.027*
H7B	0.2125	0.6096	0.2898	0.027*
C8	1.0123 (3)	0.5311 (2)	0.01195 (12)	0.0296 (4)
H8A	1.0832	0.5535	−0.0368	0.044*
H8B	1.0179	0.4248	0.0209	0.044*
H8C	1.0946	0.5823	0.0523	0.044*
C9	0.6187 (4)	0.4744 (3)	−0.06291 (11)	0.0370 (5)
H9A	0.6929	0.5007	−0.1106	0.056*
H9B	0.4538	0.4873	−0.0679	0.056*
H9C	0.6523	0.3715	−0.0507	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0209 (2)	0.0186 (2)	0.0160 (2)	0.00209 (17)	0.00126 (16)	0.00138 (16)
O1	0.0388 (8)	0.0202 (6)	0.0290 (7)	0.0101 (6)	0.0091 (6)	0.0018 (5)
O2	0.0311 (7)	0.0156 (6)	0.0220 (6)	0.0036 (5)	0.0008 (6)	−0.0003 (5)
N1	0.0200 (8)	0.0147 (7)	0.0170 (7)	−0.0002 (6)	0.0002 (6)	−0.0023 (6)
C1	0.0173 (9)	0.0194 (9)	0.0150 (8)	−0.0035 (7)	−0.0038 (7)	−0.0014 (7)
C2	0.0205 (9)	0.0190 (8)	0.0169 (9)	0.0022 (8)	0.0023 (8)	0.0016 (7)
C3	0.0178 (9)	0.0193 (9)	0.0209 (9)	−0.0004 (7)	−0.0012 (7)	0.0003 (7)
C4	0.0176 (8)	0.0165 (8)	0.0179 (9)	0.0031 (7)	−0.0021 (7)	0.0013 (7)
C5	0.0213 (10)	0.0186 (8)	0.0250 (9)	−0.0018 (8)	−0.0005 (8)	−0.0005 (7)
C6	0.0166 (9)	0.0247 (10)	0.0272 (9)	−0.0060 (8)	0.0030 (7)	−0.0001 (8)
C7	0.0236 (10)	0.0210 (8)	0.0221 (9)	−0.0006 (8)	0.0067 (8)	−0.0029 (7)
C8	0.0191 (9)	0.0384 (10)	0.0314 (10)	0.0013 (8)	0.0018 (8)	0.0086 (9)
C9	0.0366 (13)	0.0563 (13)	0.0181 (10)	−0.0149 (11)	−0.0006 (9)	−0.0074 (10)

Geometric parameters (Å, º) top

S1—C2	1.7146 (17)	C5—H5A	0.99
S1—C8	1.7851 (18)	C5—H5B	0.99
S1—C9	1.7900 (19)	C6—C7	1.538 (3)
O1—C3	1.238 (2)	C6—H6A	0.99
O2—C1	1.238 (2)	C6—H6B	0.99
N1—C1	1.381 (2)	C7—H7A	0.99
N1—C7	1.473 (2)	C7—H7B	0.99
N1—C4	1.476 (2)	C8—H8A	0.98
C1—C2	1.442 (2)	C8—H8B	0.98
C2—C3	1.408 (2)	C8—H8C	0.98
C3—C4	1.524 (2)	C9—H9A	0.98
C4—C5	1.523 (2)	C9—H9B	0.98
C4—H4	1	C9—H9C	0.98
C5—C6	1.526 (2)

C2—S1—C8	105.40 (9)	H5A—C5—H5B	109.3
C2—S1—C9	105.50 (9)	C5—C6—C7	104.11 (14)
C8—S1—C9	98.84 (11)	C5—C6—H6A	110.9
C1—N1—C7	121.50 (14)	C7—C6—H6A	110.9
C1—N1—C4	110.68 (13)	C5—C6—H6B	110.9
C7—N1—C4	111.17 (13)	C7—C6—H6B	110.9
O2—C1—N1	123.51 (15)	H6A—C6—H6B	109
O2—C1—C2	129.47 (15)	N1—C7—C6	103.08 (13)
N1—C1—C2	106.99 (14)	N1—C7—H7A	111.1
C3—C2—C1	111.43 (15)	C6—C7—H7A	111.1
C3—C2—S1	127.84 (13)	N1—C7—H7B	111.1
C1—C2—S1	120.61 (13)	C6—C7—H7B	111.1
O1—C3—C2	130.27 (16)	H7A—C7—H7B	109.1
O1—C3—C4	124.12 (15)	S1—C8—H8A	109.5
C2—C3—C4	105.60 (14)	S1—C8—H8B	109.5
N1—C4—C5	103.19 (13)	H8A—C8—H8B	109.5
N1—C4—C3	104.31 (13)	S1—C8—H8C	109.5
C5—C4—C3	118.71 (14)	H8A—C8—H8C	109.5
N1—C4—H4	110	H8B—C8—H8C	109.5
C5—C4—H4	110	S1—C9—H9A	109.5
C3—C4—H4	110	S1—C9—H9B	109.5
C4—C5—C6	101.43 (13)	H9A—C9—H9B	109.5
C4—C5—H5A	111.5	S1—C9—H9C	109.5
C6—C5—H5A	111.5	H9A—C9—H9C	109.5
C4—C5—H5B	111.5	H9B—C9—H9C	109.5
C6—C5—H5B	111.5

C7—N1—C1—O2	34.5 (2)	S1—C2—C3—C4	179.92 (13)
C4—N1—C1—O2	167.62 (15)	C1—N1—C4—C5	−116.83 (15)
C7—N1—C1—C2	−143.55 (15)	C7—N1—C4—C5	21.34 (17)
C4—N1—C1—C2	−10.39 (18)	C1—N1—C4—C3	7.84 (18)
O2—C1—C2—C3	−168.74 (17)	C7—N1—C4—C3	146.01 (13)
N1—C1—C2—C3	9.1 (2)	O1—C3—C4—N1	176.79 (16)
O2—C1—C2—S1	7.6 (3)	C2—C3—C4—N1	−2.07 (18)
N1—C1—C2—S1	−174.58 (12)	O1—C3—C4—C5	−69.1 (2)
C8—S1—C2—C3	−52.18 (19)	C2—C3—C4—C5	112.01 (16)
C9—S1—C2—C3	51.81 (19)	N1—C4—C5—C6	−37.44 (16)
C8—S1—C2—C1	132.16 (15)	C3—C4—C5—C6	−152.13 (15)
C9—S1—C2—C1	−123.85 (16)	C4—C5—C6—C7	40.51 (17)
C1—C2—C3—O1	177.13 (18)	C1—N1—C7—C6	136.85 (15)
S1—C2—C3—O1	1.1 (3)	C4—N1—C7—C6	3.89 (18)
C1—C2—C3—C4	−4.1 (2)	C5—C6—C7—N1	−27.69 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	1.00	2.55	3.4145 (19)	145
C7—H7B···O1ⁱⁱ	0.99	2.59	3.570 (2)	173

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

Experimental details

Crystal data
Chemical formula	C₉H₁₃NO₂S
M_r	199.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	130
a, b, c (Å)	5.8761 (3), 9.0858 (5), 17.7107 (9)
V (Å³)	945.56 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.46 × 0.33 × 0.07

Data collection
Diffractometer	Oxford Xcalibur Atlas Gemini diffractometer
Absorption correction	Analytical (CrysAlis PRO; Oxford Diffraction, 2002)
T_min, T_max	0.895, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	6356, 1873, 1736
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.065, 1.04
No. of reflections	1873
No. of parameters	120
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.26
Absolute structure	Flack (1983), with 758 Friedel pairs
Absolute structure parameter	−0.07 (7)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2002), CrysAlis RED (Oxford Diffraction, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	1.00	2.55	3.4145 (19)	145
C7—H7B···O1ⁱⁱ	0.99	2.59	3.570 (2)	173

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

Acknowledgements

The authors are grateful to BUAP (Project VIEP 2011) for financial support. LGL thanks VIEP for a scholarship.

References

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o752

doi:10.1107/S1600536812003601

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

(7aS)-(–)-Dimeth­yl(1-oxido-3-oxo-5,6,7,7a-tetra­hydro-3H-pyrrolizin-2-yl)sulfonium

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(7aS)-(–)-Dimethyl(1-oxido-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)sulfonium