(R)-(+)-Dimeth­yl[4-oxido-2-oxo-1-(1-phenyl­eth­yl)-1,2,5,6-tetra­hydro­pyridin-3-yl]sulfonium

Gordillo, P.G.; Terán, J.L.; Juárez, J.R.; Mendoza, A.

doi:10.1107/S1600536810052955

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o239

doi:10.1107/S1600536810052955

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(R)-(+)-Dimethyl[4-oxido-2-oxo-1-(1-phenylethyl)-1,2,5,6-tetrahydropyridin-3-yl]sulfonium

Paola G. Gordillo,^a Joel L. Terán,^a Jorge R. Juárez ^a and Angel Mendoza ^a ^*

^aCentro de Química, ICUAP, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Pue., Mexico
^*Correspondence e-mail: angel.mendoza.m@gmail.com

(Received 14 December 2010; accepted 16 December 2010; online 8 January 2011)

In the title zwitterionic compound, C₁₅H₁₉NO₂S, the six-membered heterocycle adopts a sofa conformation. The negative charge is delocalized along the carbonyl and enolate system on the ring and the positive charge is localized on the S atom. Two intermolecular C—H⋯O interactions help to establish the packing.

Related literature

For background to the synthesis of chiral non-racemic zwitterionic 4-alkoxy-3-sulfonium ylide pyridine-2-ones, 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 ); Koruzňjak et al., 2003 ). For ring conformation analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₅H₁₉NO₂S
M_r = 277.37
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.9860 (17) Å
b = 7.4050 (14) Å
c = 31.589 (5) Å
V = 1400.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.5 × 0.4 × 0.2 mm

Data collection

Siemens P4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.728, T_max = 0.846
3016 measured reflections
2683 independent reflections
1928 reflections with I > 2σ(I)
R_int = 0.045
3 standard reflections every 97 reflections intensity decay: 3%

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.153
S = 1.03
2683 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ), 532 Friedel pairs
Flack parameter: −0.01 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7C⋯O2ⁱ	0.96	2.36	3.315 (6)	172
C15—H15A⋯O1ⁱⁱ	0.96	2.38	3.167 (5)	138
Symmetry codes: (i) x-1, y-1, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: XSCANS (Siemens, 1994 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); 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/S1600536810052955/bt5438sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810052955/bt5438Isup2.hkl

checkCIF report

Comment top

The synthesis of chiral non racemic zwitterionic 4-alkoxy-3-sulfonium ylide pyridine-2-ones is an original area of interest in organic chemistry (Zang et al., 2008; Kappe et al., 1983) because they are useful for the synthesis of piperidine-2,4-dione and pyridine-2-one (Palillero et al., 2009) compounds and because of their interesting biological properties (Basco et al., 1994; Koruzňjak et al., 2003).

The title compound I, features a zwitterionic molecule. The chiral centre shows an R configuration with [α]_D= +70.5. The six member ring N1/C1/C2/C3/C4/C5 shows an sofa conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.465 (4) Å, θ₂ = 119.7 (5)°, ϕ₂ = 103.2 (6)°, q₂ = 0.404 (4) Å and q₃ = -0.231 (4) Å. The bond distances of N1—C1, N1—C5, C5—C4 and C4—C3 show typical values, so that C2—C3 distance shows a single double bond (1.415 (5) Å), while C1—C2 (1.455 (5) Å) distance is shorter than common sp³—sp³ bonds, furthermore C3—O2 (1.244 (5) Å) and C1—O1 (1.250 (4) Å) distances are longer than related enolates and amide groups respectively these values suggest that negative charge is delocalized over O1/C1/C2/C3/O2 system and in the sulfonium group is located the positive charge in the zwitterion. Crystal packing is stabilized by two weak intermolecular C —H···O interactions.

Related literature top

For background to the synthesis of chiral non-racemic zwitterionic 4-alkoxy-3-sulfonium ylide pyridine-2-ones, 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); Koruzňjak et al., 2003). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental top

The title compound, was obtained by an intramolecular cyclization reaction of (1'R)-(+)-{[(2-methoxycarbonyl-ethyl)-(1'-phenyl-ethyl)-carbamoyl]-methyl}-dimethyl-sulfonium; bromide (1 mmol), which was dissolved in CH₃CN (10 mL), treated with KOH (1.2 mmol) and stirred for two hours at room temperature. The resulting mixture was concentrated in vacuum and dissolved in ethyl acetate, filtered and concentrated giving the desired compound in 95%. Crystals were obtained from an ethyl acetate/diethylether solution; m.p. 139–140°C, [α]_D= +70.5 (c 1.1, MeOH). IR (KBr) 1656 cm^{-1. 1}H NMR (400 MHz, CDCl₃) δ (p.p.m., J Hz): 1.51 (d, J = 7.2, 3H, Me), 2.32 (m, 2H), 2.90 (m, 1H), 2.98 (s, 3H, SMe), 3.00 (s, 3H, SMe), 3.16 (m, 1H), 5.94 (q, J =7.2, 1H), 7.27–7.40 (m, 5H). ¹³C NMR (100 MHz, CDCl₃) δ p.p.m. 15.4, 26.0, 26.3, 36.3, 37.6, 48.9, 74.3, 126.5–141.0, 166.2, 187.5. HRMS (FAB): Calcd for C₁₅H₁₉NO₂S: 277.1124. Found: 277.1103.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: XSCANS (Siemens, 1994); program(s) used to solve structure: SIR2004 (Burla et al., 2005); 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 the title compound with 50% probability displacement ellipsoids for non-H atoms.

(R)-(+)-Dimethyl[4-oxido-2-oxo-1-(1-phenylethyl)-1,2,5,6- tetrahydropyridin-3-yl]sulfonium top

Crystal data top

C₁₅H₁₉NO₂S	F(000) = 592
M_r = 277.37	D_x = 1.316 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 46 reflections
a = 5.9860 (17) Å	θ = 21.3–35.1°
b = 7.4050 (14) Å	µ = 0.23 mm⁻¹
c = 31.589 (5) Å	T = 293 K
V = 1400.2 (5) Å³	Prism, colorless
Z = 4	0.5 × 0.4 × 0.2 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.045
Graphite monochromator	θ_max = 29.0°, θ_min = 2.6°
2θ/ω scans	h = −1→8
Absorption correction: ψ scan (North et al., 1968)	k = −1→10
T_min = 0.728, T_max = 0.846	l = −43→1
3016 measured reflections	3 standard reflections every 97 reflections
2683 independent reflections	intensity decay: 3%
1928 reflections with I > 2σ(I)

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)] = 0.061	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0631P)² + 1.1965P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2683 reflections	Δρ_max = 0.63 e Å⁻³
172 parameters	Δρ_min = −0.39 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 532 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (16)

Crystal data top

C₁₅H₁₉NO₂S	V = 1400.2 (5) Å³
M_r = 277.37	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.9860 (17) Å	µ = 0.23 mm⁻¹
b = 7.4050 (14) Å	T = 293 K
c = 31.589 (5) Å	0.5 × 0.4 × 0.2 mm

Data collection top

Siemens P4 diffractometer	1928 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.045
T_min = 0.728, T_max = 0.846	3 standard reflections every 97 reflections
3016 measured reflections	intensity decay: 3%
2683 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.153	Δρ_max = 0.63 e Å⁻³
S = 1.03	Δρ_min = −0.39 e Å⁻³
2683 reflections	Absolute structure: Flack (1983), 532 Friedel pairs
172 parameters	Absolute structure parameter: −0.01 (16)
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	1.10027 (19)	0.87732 (14)	0.03372 (3)	0.0323 (2)
O1	0.8859 (6)	0.5383 (4)	0.05505 (8)	0.0393 (7)
N1	0.7630 (6)	0.6122 (4)	0.12114 (10)	0.0300 (7)
O2	1.0851 (7)	1.1013 (4)	0.11356 (10)	0.0511 (9)
C9	0.8558 (7)	0.3759 (6)	0.19114 (12)	0.0351 (9)
H9	0.9723	0.4434	0.1798	0.042*
C1	0.8724 (7)	0.6511 (5)	0.08437 (10)	0.0278 (8)
C6	0.6341 (8)	0.4423 (5)	0.12418 (12)	0.0345 (10)
H6	0.7011	0.3572	0.1041	0.041*
C4	0.8971 (9)	0.8843 (6)	0.15731 (11)	0.0373 (9)
H4A	1.0124	0.8199	0.1727	0.045*
H4B	0.8501	0.9863	0.1744	0.045*
C3	0.9911 (8)	0.9518 (6)	0.11576 (12)	0.0340 (9)
C8	0.6557 (7)	0.3579 (5)	0.16847 (12)	0.0305 (9)
C10	0.8816 (9)	0.2937 (6)	0.23044 (13)	0.0404 (10)
H10	1.0143	0.3077	0.2454	0.049*
C15	1.3821 (8)	0.9447 (7)	0.04512 (13)	0.0427 (11)
H15A	1.4586	0.9711	0.0191	0.064*
H15B	1.4578	0.8487	0.0596	0.064*
H15C	1.3805	1.0505	0.0627	0.064*
C2	0.9708 (7)	0.8304 (5)	0.08140 (11)	0.0285 (9)
C5	0.7006 (8)	0.7604 (6)	0.14990 (12)	0.0345 (10)
H5A	0.6507	0.7108	0.1767	0.041*
H5B	0.578	0.8286	0.1377	0.041*
C13	0.4867 (8)	0.2558 (6)	0.18589 (14)	0.0396 (10)
H13	0.3523	0.2426	0.1714	0.048*
C12	0.5156 (9)	0.1720 (6)	0.22507 (14)	0.0445 (11)
H12	0.401	0.1021	0.2363	0.053*
C11	0.7107 (9)	0.1916 (6)	0.24725 (14)	0.0443 (12)
H11	0.7278	0.1363	0.2735	0.053*
C14	0.9890 (9)	1.0887 (7)	0.01517 (15)	0.0544 (13)
H14A	1.0569	1.1193	−0.0114	0.082*
H14B	1.0205	1.1817	0.0355	0.082*
H14C	0.8304	1.078	0.0115	0.082*
C7	0.3927 (9)	0.4733 (7)	0.10987 (16)	0.0524 (13)
H7A	0.3922	0.5252	0.082	0.079*
H7B	0.3199	0.5539	0.1293	0.079*
H7C	0.3147	0.36	0.1094	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0354 (5)	0.0314 (4)	0.0300 (4)	−0.0059 (5)	0.0034 (5)	0.0035 (4)
O1	0.056 (2)	0.0317 (14)	0.0304 (13)	−0.0091 (19)	0.0042 (15)	−0.0028 (11)
N1	0.0319 (17)	0.0246 (15)	0.0334 (15)	−0.0086 (18)	0.0047 (14)	0.0014 (14)
O2	0.066 (2)	0.0325 (15)	0.0543 (17)	−0.023 (2)	0.0150 (19)	−0.0100 (13)
C9	0.034 (2)	0.0334 (19)	0.0379 (19)	−0.002 (2)	0.0054 (17)	0.0015 (18)
C1	0.030 (2)	0.0288 (18)	0.0245 (15)	−0.003 (2)	−0.0033 (16)	0.0029 (14)
C6	0.040 (3)	0.0282 (18)	0.0352 (19)	−0.010 (2)	0.0001 (19)	0.0041 (16)
C4	0.052 (2)	0.0315 (18)	0.0287 (17)	−0.007 (3)	0.009 (2)	−0.0067 (16)
C3	0.037 (2)	0.0305 (19)	0.0348 (19)	−0.003 (2)	0.0052 (19)	−0.0037 (17)
C8	0.036 (2)	0.0214 (17)	0.0341 (18)	0.0030 (19)	0.0052 (17)	−0.0042 (15)
C10	0.042 (2)	0.041 (2)	0.039 (2)	0.006 (3)	−0.001 (2)	−0.0008 (18)
C15	0.031 (2)	0.055 (3)	0.042 (2)	−0.006 (3)	0.008 (2)	0.001 (2)
C2	0.033 (2)	0.0234 (17)	0.0292 (17)	−0.0035 (18)	0.0036 (16)	0.0020 (14)
C5	0.042 (2)	0.030 (2)	0.0321 (19)	−0.002 (2)	0.0077 (19)	−0.0005 (16)
C13	0.034 (2)	0.037 (2)	0.048 (2)	−0.003 (2)	0.001 (2)	0.0091 (19)
C12	0.046 (3)	0.040 (2)	0.048 (3)	−0.006 (3)	0.012 (2)	0.013 (2)
C11	0.057 (3)	0.041 (2)	0.035 (2)	0.013 (3)	0.009 (2)	0.0050 (19)
C14	0.051 (3)	0.057 (3)	0.055 (3)	0.004 (3)	0.004 (2)	0.026 (2)
C7	0.042 (3)	0.057 (3)	0.058 (3)	−0.016 (3)	−0.015 (3)	0.019 (2)

Geometric parameters (Å, º) top

S1—C2	1.729 (4)	C8—C13	1.378 (6)
S1—C15	1.796 (5)	C10—C11	1.379 (7)
S1—C14	1.799 (5)	C10—H10	0.93
O1—C1	1.250 (4)	C15—H15A	0.96
N1—C1	1.364 (5)	C15—H15B	0.96
N1—C5	1.473 (5)	C15—H15C	0.96
N1—C6	1.479 (5)	C5—H5A	0.97
O2—C3	1.244 (5)	C5—H5B	0.97
C9—C10	1.391 (6)	C13—C12	1.395 (6)
C9—C8	1.402 (6)	C13—H13	0.93
C9—H9	0.93	C12—C11	1.369 (7)
C1—C2	1.455 (5)	C12—H12	0.93
C6—C7	1.531 (7)	C11—H11	0.93
C6—C8	1.538 (5)	C14—H14A	0.96
C6—H6	0.98	C14—H14B	0.96
C4—C5	1.510 (6)	C14—H14C	0.96
C4—C3	1.513 (5)	C7—H7A	0.96
C4—H4A	0.97	C7—H7B	0.96
C4—H4B	0.97	C7—H7C	0.96
C3—C2	1.415 (5)

C2—S1—C15	107.6 (2)	H15A—C15—H15B	109.5
C2—S1—C14	107.0 (2)	S1—C15—H15C	109.5
C15—S1—C14	99.9 (2)	H15A—C15—H15C	109.5
C1—N1—C5	119.4 (3)	H15B—C15—H15C	109.5
C1—N1—C6	119.0 (3)	C3—C2—C1	124.4 (3)
C5—N1—C6	117.5 (3)	C3—C2—S1	120.1 (3)
C10—C9—C8	120.6 (4)	C1—C2—S1	114.9 (3)
C10—C9—H9	119.7	N1—C5—C4	110.5 (3)
C8—C9—H9	119.7	N1—C5—H5A	109.5
O1—C1—N1	121.4 (3)	C4—C5—H5A	109.5
O1—C1—C2	122.4 (3)	N1—C5—H5B	109.5
N1—C1—C2	116.2 (3)	C4—C5—H5B	109.5
N1—C6—C7	110.2 (4)	H5A—C5—H5B	108.1
N1—C6—C8	111.2 (3)	C8—C13—C12	120.5 (4)
C7—C6—C8	114.1 (4)	C8—C13—H13	119.8
N1—C6—H6	107	C12—C13—H13	119.8
C7—C6—H6	107	C11—C12—C13	120.9 (4)
C8—C6—H6	107	C11—C12—H12	119.6
C5—C4—C3	110.8 (3)	C13—C12—H12	119.6
C5—C4—H4A	109.5	C12—C11—C10	119.6 (4)
C3—C4—H4A	109.5	C12—C11—H11	120.2
C5—C4—H4B	109.5	C10—C11—H11	120.2
C3—C4—H4B	109.5	S1—C14—H14A	109.5
H4A—C4—H4B	108.1	S1—C14—H14B	109.5
O2—C3—C2	124.2 (4)	H14A—C14—H14B	109.5
O2—C3—C4	120.7 (4)	S1—C14—H14C	109.5
C2—C3—C4	115.1 (3)	H14A—C14—H14C	109.5
C13—C8—C9	118.4 (4)	H14B—C14—H14C	109.5
C13—C8—C6	121.6 (4)	C6—C7—H7A	109.5
C9—C8—C6	119.9 (4)	C6—C7—H7B	109.5
C11—C10—C9	120.1 (5)	H7A—C7—H7B	109.5
C11—C10—H10	120	C6—C7—H7C	109.5
C9—C10—H10	120	H7A—C7—H7C	109.5
S1—C15—H15A	109.5	H7B—C7—H7C	109.5
S1—C15—H15B	109.5

C5—N1—C1—O1	−164.3 (4)	O2—C3—C2—S1	5.4 (7)
C6—N1—C1—O1	−7.7 (6)	C4—C3—C2—S1	−172.1 (3)
C5—N1—C1—C2	15.5 (5)	O1—C1—C2—C3	−169.5 (4)
C6—N1—C1—C2	172.0 (3)	N1—C1—C2—C3	10.7 (6)
C1—N1—C6—C7	−90.2 (5)	O1—C1—C2—S1	1.8 (5)
C5—N1—C6—C7	66.8 (5)	N1—C1—C2—S1	−178.0 (3)
C1—N1—C6—C8	142.2 (4)	C15—S1—C2—C3	46.9 (4)
C5—N1—C6—C8	−60.8 (5)	C14—S1—C2—C3	−59.6 (4)
C5—C4—C3—O2	151.0 (4)	C15—S1—C2—C1	−124.8 (3)
C5—C4—C3—C2	−31.4 (6)	C14—S1—C2—C1	128.7 (3)
C10—C9—C8—C13	−0.6 (6)	C1—N1—C5—C4	−48.4 (5)
C10—C9—C8—C6	−177.2 (4)	C6—N1—C5—C4	154.7 (3)
N1—C6—C8—C13	149.8 (4)	C3—C4—C5—N1	54.5 (5)
C7—C6—C8—C13	24.4 (6)	C9—C8—C13—C12	−0.3 (6)
N1—C6—C8—C9	−33.6 (5)	C6—C8—C13—C12	176.3 (4)
C7—C6—C8—C9	−159.1 (4)	C8—C13—C12—C11	0.9 (7)
C8—C9—C10—C11	0.8 (6)	C13—C12—C11—C10	−0.7 (7)
O2—C3—C2—C1	176.3 (4)	C9—C10—C11—C12	−0.2 (7)
C4—C3—C2—C1	−1.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7C···O2ⁱ	0.96	2.36	3.315 (6)	172
C15—H15A···O1ⁱⁱ	0.96	2.38	3.167 (5)	138

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₉NO₂S
M_r	277.37
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	5.9860 (17), 7.4050 (14), 31.589 (5)
V (Å³)	1400.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.5 × 0.4 × 0.2

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.728, 0.846
No. of measured, independent and observed [I > 2σ(I)] reflections	3016, 2683, 1928
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.153, 1.03
No. of reflections	2683
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.39
Absolute structure	Flack (1983), 532 Friedel pairs
Absolute structure parameter	−0.01 (16)

Computer programs: XSCANS (Siemens, 1994), SIR2004 (Burla et al., 2005), 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
C7—H7C···O2ⁱ	0.96	2.36	3.315 (6)	172
C15—H15A···O1ⁱⁱ	0.96	2.38	3.167 (5)	138

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

Acknowledgements

We are grateful to CONACyT (Project 83185) for financial support. PGG also thanks CONACyT for a scholarship (169011). Special thanks go to Dr Marcos Flores (USAI-FQ-UNAM) for useful comments.

References

Basco, L. K., Mitaku, S., Skaltsounis, A. L., Ravelomanantsoa, N., Tillequin, F., Koch, M. & Le Bras, J. (1994). J. Antimicrob. Agents Chemother. 38, 1169–1171. CrossRef CAS Google Scholar
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Volume 67| Part 2| February 2011| Page o239

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

(R)-(+)-Dimeth­yl[4-oxido-2-oxo-1-(1-phenyl­eth­yl)-1,2,5,6-tetra­hydro­pyridin-3-yl]sulfonium

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(R)-(+)-Dimethyl[4-oxido-2-oxo-1-(1-phenylethyl)-1,2,5,6-tetrahydropyridin-3-yl]sulfonium