(5S,11aS)-5-Hydro­per­oxy-1,5,11,11a-tetra­hydro­[1]benzothieno[3,2-f]indol­izin-3(2H)-one

Vrábel, V.; Švorc, Ľ.; Marchalín, Š.; Šafář, P.

doi:10.1107/S1600536812045394

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3327-o3328

doi:10.1107/S1600536812045394

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(5S,11aS)-5-Hydroperoxy-1,5,11,11a-tetrahydro[1]benzothieno[3,2-f]indolizin-3(2H)-one

Viktor Vrábel,^a ^* Ľubomír Švorc,^a Štefan Marchalín ^b and Peter Šafář ^b

^aInstitute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^bInstitute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
^*Correspondence e-mail: viktor.vrabel@stuba.sk

(Received 11 September 2012; accepted 2 November 2012; online 10 November 2012)

The absolute configuration of the title compound, C₁₄H₁₃NO₃S, was assigned from the synthesis and confirmed by the structure determination. The central six-membered ring of the indolizine moiety adopts an envelope conformation, with the greatest deviation from the mean plane of the ring being 0.661 (2) Å for the bridgehead C atom. The benzothiene ring attached to the indolizine ring system is planar to within 0.008 (2) Å. In the crystal, molecules form chains parallel to the b axis via O—H⋯O hydrogen bonds.

Related literature

For background to indolizines and their biological activity, see: Malonne et al. (1998 ); Medda et al. (2003 ); Sonnet et al. (2000 ); Campagna et al. (1990 ); Pearson & Guo (2001 ). For their synthesis, see: Šafář et al. (2009a ,b ). For compounds with similar properties, see: Švorc et al. (2008 , 2009 ). For IR spectroscopy on similar compounds, see: Šafář et al. (2009a). For conformational analysis, see: Nardelli (1983 ).

Experimental

Crystal data

C₁₄H₁₃NO₃S
M_r = 275.31
Monoclinic, P 2₁
a = 7.8040 (5) Å
b = 7.9800 (4) Å
c = 10.2903 (5) Å
β = 99.458 (5)°
V = 632.13 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 295 K
0.25 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur (Ruby, Gemi) diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.947, T_max = 0.974
21595 measured reflections
2555 independent reflections
2162 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.068
S = 1.00
2555 reflections
176 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ), 1185 Friedel pairs
Flack parameter: −0.05 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1ⁱ	0.84 (1)	1.86 (1)	2.6962 (19)	173 (2)
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND, (Brandenburg, 2001 ), PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812045394/bg2481sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045394/bg2481Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812045394/bg2481Isup3.cml

checkCIF report

Comment top

Heterocycles are involved in a wide range of biologically important chemical reactions in living organisms, and therefore they form one of the most important and well investigated classes of organic compounds. One group of heterocycles, indolizines, has received much scientific attention during the recent years. Indolizine derivatives have been found to possess a variety of biological activities such as antiinflammatory (Malonne et al., 1998), antiviral (Medda et al., 2003), aromatase inhibitory (Sonnet et al., 2000), analgestic (Campagna et al., 1990) and antitumor (Pearson & Guo, 2001) activities. As part of our recent efforts to synthesize novel polycyclic indolizine derivative, we report here the synthesis and molecular and crystal structure of the title compound, (I) (Fig. 1). The absolute configuration has been established without ambiguity from the anomalous dispersion of the S atom (Flack, 1983) and assigned consistent with the starting material. The expected stereochemistry of both atoms C5 and C15 was confirmed as S, see Fig. 1. The central N-heterocyclic ring is not planar and adopts a envelope conformation (Nardelli, 1983). A calculation of least-squares planes shows that this ring is puckered in such a manner that the five atoms C6, C7, C14, C15 and N1 are planar to within 0.075 (3) Å, while atom C5 is displaced from this plane with out-of-plane displacement of 0.661 (2) Å. The pyrrolidine ring is distorted towards a flat-envelope conformation, with atom C4 on the flap. Atom C4 is 0.402 (2) Å from the mean plane defined by atoms C5, N1, C2 and C3. The dihedral angle between the plane of the central N-heterocyclic ring and the plane of the pyrrolidine ring is 44.6 (1)°. Atom N1 is sp²-hybridized, as evidenced by the sum of the valence angles around it (358.1°). These data are consistent with conjugation of the lone-pair electrons on N1 with the adjacent carbonyl, similar to what is observed for amides. Intermolecular O—H···O hydrogen bonds link the molecules into infinite chains, which run parallel to the b axis (Fig. 2) and help to stabilize the crystal structure of the compound. The bond lengths of the carbonyl group C2=O1 is 1.233 (2) Å somewhat longer than typical carbonyl bonds. This may be due to the fact that atom O1 participates in intermolecular hydrogen bond.

Related literature top

For background to indolizines and their biological activity, see: Malonne et al. (1998); Medda et al. (2003); Sonnet et al. (2000); Campagna et al. (1990); Pearson & Guo (2001). For their synthesis, see: Šafář et al. (2009a,b). For compounds with similar properties, see: Švorc et al. (2008, 2009). For IR spectroscopy on similar compounds, see: Šafář et al. (2009a). For conformational analysis, see: Nardelli (1983).

Experimental top

To a solution of (11aS)-1,5,11,11a-tetrahydro[1]benzothieno[3,2-f] indolizin-3(2H)-one (0.041 mmol) in THF (2 ml) was added 3 drops of H₂O₂ at 0°C and the mixture was allowed to react at room temperature for 72 h. The colorless crystals were filtered off, and washing with dry n-hexane (1 ml) gave pure indolizinhydroperoxid.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND, (Brandenburg, 2001), PLATON (Spek, 2009) and WinGX (Farrugia, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level (Brandenburg, 2001).
	Fig. 2. Packing view of the title compound. Molecular links are generated by O–H···O hydrogen bonds along the b axis which are shown by green dashed lines (Brandenburg, 2001).

(5S,11aS)-5-Hydroperoxy-1,5,11,11a- tetrahydro[1]benzothieno[3,2-f]indolizin-3(2H)-one top

Crystal data top

C₁₄H₁₃NO₃S	F(000) = 288
M_r = 275.31	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 10799 reflections
a = 7.8040 (5) Å	θ = 3.2–29.6°
b = 7.9800 (4) Å	µ = 0.26 mm⁻¹
c = 10.2903 (5) Å	T = 295 K
β = 99.458 (5)°	Block, colourless
V = 632.13 (6) Å³	0.25 × 0.20 × 0.15 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur (Ruby, Gemi) diffractometer	2555 independent reflections
Radiation source: fine-focus sealed tube	2162 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 10.4340 pixels mm^-1	θ_max = 26.4°, θ_min = 4.4°
ω scans	h = −9→9
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −9→9
T_min = 0.947, T_max = 0.974	l = −12→12
21595 measured reflections

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 atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.0441P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2555 reflections	Δρ_max = 0.13 e Å⁻³
176 parameters	Δρ_min = −0.14 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1185 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (6)

Crystal data top

C₁₄H₁₃NO₃S	V = 632.13 (6) Å³
M_r = 275.31	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.8040 (5) Å	µ = 0.26 mm⁻¹
b = 7.9800 (4) Å	T = 295 K
c = 10.2903 (5) Å	0.25 × 0.20 × 0.15 mm
β = 99.458 (5)°

Data collection top

Oxford Diffraction Xcalibur (Ruby, Gemi) diffractometer	2555 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	2162 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.974	R_int = 0.028
21595 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.068	Δρ_max = 0.13 e Å⁻³
S = 1.00	Δρ_min = −0.14 e Å⁻³
2555 reflections	Absolute structure: Flack (1983), 1185 Friedel pairs
176 parameters	Absolute structure parameter: −0.05 (6)
2 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
C2	−0.1152 (2)	0.0934 (2)	0.10939 (14)	0.0487 (4)
C3	−0.2994 (2)	0.1556 (3)	0.07868 (18)	0.0625 (5)
H3B	−0.3714	0.1014	0.1347	0.075*
H3A	−0.3483	0.1340	−0.0127	0.075*
C4	−0.2872 (2)	0.3432 (3)	0.1057 (2)	0.0662 (5)
H4B	−0.3852	0.3817	0.1447	0.079*
H4A	−0.2838	0.4054	0.0252	0.079*
C5	−0.1161 (2)	0.3639 (3)	0.20284 (16)	0.0527 (4)
H5	−0.0563	0.4666	0.1834	0.063*
C6	−0.1345 (2)	0.3584 (3)	0.34751 (18)	0.0584 (4)
H6B	−0.1750	0.4661	0.3741	0.070*
H6A	−0.2190	0.2739	0.3613	0.070*
C7	0.0371 (2)	0.31816 (19)	0.42819 (16)	0.0490 (4)
C8	0.2927 (2)	0.2798 (2)	0.60665 (15)	0.0497 (4)
C9	0.4223 (3)	0.2701 (3)	0.71705 (16)	0.0633 (5)
H9	0.4012	0.3056	0.7990	0.076*
C10	0.5810 (3)	0.2073 (3)	0.70255 (19)	0.0707 (6)
H10	0.6691	0.2028	0.7752	0.085*
C11	0.6131 (3)	0.1499 (3)	0.58133 (19)	0.0634 (5)
H11	0.7218	0.1064	0.5743	0.076*
C12	0.4862 (2)	0.1569 (2)	0.47181 (16)	0.0511 (4)
H12	0.5084	0.1174	0.3912	0.061*
C13	0.3233 (2)	0.22356 (19)	0.48218 (15)	0.0428 (4)
C14	0.17251 (19)	0.24634 (19)	0.38248 (14)	0.0412 (4)
C15	0.15873 (19)	0.1929 (2)	0.24080 (14)	0.0413 (4)
H15	0.1927	0.0751	0.2363	0.050*
N1	−0.01704 (17)	0.21547 (16)	0.17396 (12)	0.0447 (3)
O1	−0.06189 (17)	−0.04709 (17)	0.08604 (12)	0.0627 (3)
O2	0.27750 (15)	0.29669 (15)	0.18624 (11)	0.0513 (3)
O3	0.28192 (17)	0.23328 (18)	0.05339 (11)	0.0597 (3)
H3	0.207 (2)	0.299 (3)	0.013 (2)	0.098 (9)*
S1	0.08315 (6)	0.35880 (6)	0.59656 (4)	0.06228 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0512 (10)	0.0610 (11)	0.0332 (7)	−0.0060 (9)	0.0043 (7)	0.0038 (8)
C3	0.0518 (11)	0.0782 (14)	0.0546 (10)	−0.0038 (10)	0.0001 (8)	0.0057 (9)
C4	0.0501 (10)	0.0692 (13)	0.0765 (12)	0.0052 (11)	0.0018 (9)	0.0209 (11)
C5	0.0440 (9)	0.0452 (9)	0.0699 (10)	0.0038 (9)	0.0121 (8)	0.0093 (9)
C6	0.0508 (9)	0.0560 (9)	0.0702 (10)	0.0095 (10)	0.0151 (8)	−0.0066 (10)
C7	0.0520 (10)	0.0446 (10)	0.0529 (9)	−0.0003 (8)	0.0156 (8)	−0.0048 (7)
C8	0.0679 (11)	0.0400 (8)	0.0435 (9)	0.0012 (8)	0.0161 (8)	0.0007 (7)
C9	0.0933 (15)	0.0563 (11)	0.0402 (9)	0.0050 (11)	0.0102 (9)	0.0006 (8)
C10	0.0872 (16)	0.0703 (14)	0.0492 (10)	0.0112 (12)	−0.0050 (10)	0.0097 (9)
C11	0.0673 (12)	0.0648 (12)	0.0560 (10)	0.0171 (10)	0.0042 (9)	0.0099 (9)
C12	0.0589 (11)	0.0514 (10)	0.0439 (9)	0.0086 (9)	0.0111 (8)	0.0041 (7)
C13	0.0549 (9)	0.0338 (8)	0.0411 (7)	−0.0015 (7)	0.0120 (7)	0.0016 (6)
C14	0.0467 (9)	0.0354 (8)	0.0433 (8)	−0.0009 (7)	0.0125 (7)	−0.0009 (6)
C15	0.0405 (8)	0.0433 (9)	0.0408 (8)	−0.0002 (7)	0.0084 (6)	0.0009 (6)
N1	0.0429 (7)	0.0457 (7)	0.0458 (7)	0.0001 (6)	0.0082 (6)	0.0021 (6)
O1	0.0674 (9)	0.0619 (8)	0.0554 (7)	−0.0007 (7)	0.0000 (6)	−0.0159 (6)
O2	0.0498 (6)	0.0609 (7)	0.0445 (6)	−0.0061 (5)	0.0121 (5)	0.0000 (5)
O3	0.0607 (8)	0.0756 (9)	0.0452 (7)	0.0118 (7)	0.0163 (6)	0.0007 (6)
S1	0.0745 (3)	0.0630 (3)	0.0537 (2)	0.0086 (3)	0.0234 (2)	−0.0118 (2)

Geometric parameters (Å, º) top

C2—O1	1.233 (2)	C8—C13	1.414 (2)
C2—N1	1.345 (2)	C8—S1	1.7400 (19)
C2—C3	1.505 (3)	C9—C10	1.366 (3)
C3—C4	1.523 (3)	C9—H9	0.9300
C3—H3B	0.9700	C10—C11	1.390 (3)
C3—H3A	0.9700	C10—H10	0.9300
C4—C5	1.539 (3)	C11—C12	1.374 (3)
C4—H4B	0.9700	C11—H11	0.9300
C4—H4A	0.9700	C12—C13	1.398 (2)
C5—N1	1.471 (2)	C12—H12	0.9300
C5—C6	1.519 (2)	C13—C14	1.440 (2)
C5—H5	0.9800	C14—C15	1.506 (2)
C6—C7	1.490 (2)	C15—O2	1.4252 (19)
C6—H6B	0.9700	C15—N1	1.441 (2)
C6—H6A	0.9700	C15—H15	0.9800
C7—C14	1.353 (2)	O2—O3	1.4634 (16)
C7—S1	1.7411 (17)	O3—H3	0.841 (2)
C8—C9	1.393 (3)

O1—C2—N1	124.86 (17)	C13—C8—S1	110.95 (13)
O1—C2—C3	126.89 (16)	C10—C9—C8	118.72 (16)
N1—C2—C3	108.17 (16)	C10—C9—H9	120.6
C2—C3—C4	104.88 (16)	C8—C9—H9	120.6
C2—C3—H3B	110.8	C9—C10—C11	121.29 (18)
C4—C3—H3B	110.8	C9—C10—H10	119.4
C2—C3—H3A	110.8	C11—C10—H10	119.4
C4—C3—H3A	110.8	C12—C11—C10	120.70 (18)
H3B—C3—H3A	108.8	C12—C11—H11	119.7
C3—C4—C5	104.22 (16)	C10—C11—H11	119.7
C3—C4—H4B	110.9	C11—C12—C13	119.67 (15)
C5—C4—H4B	110.9	C11—C12—H12	120.2
C3—C4—H4A	110.9	C13—C12—H12	120.2
C5—C4—H4A	110.9	C12—C13—C8	118.72 (15)
H4B—C4—H4A	108.9	C12—C13—C14	129.82 (14)
N1—C5—C6	108.21 (14)	C8—C13—C14	111.46 (14)
N1—C5—C4	102.19 (16)	C7—C14—C13	113.53 (14)
C6—C5—C4	114.92 (14)	C7—C14—C15	121.41 (14)
N1—C5—H5	110.4	C13—C14—C15	125.04 (13)
C6—C5—H5	110.4	O2—C15—N1	111.66 (12)
C4—C5—H5	110.4	O2—C15—C14	105.62 (12)
C7—C6—C5	109.33 (13)	N1—C15—C14	109.74 (12)
C7—C6—H6B	109.8	O2—C15—H15	109.9
C5—C6—H6B	109.8	N1—C15—H15	109.9
C7—C6—H6A	109.8	C14—C15—H15	109.9
C5—C6—H6A	109.8	C2—N1—C15	124.42 (15)
H6B—C6—H6A	108.3	C2—N1—C5	114.03 (14)
C14—C7—C6	125.42 (15)	C15—N1—C5	119.65 (13)
C14—C7—S1	112.32 (13)	C15—O2—O3	106.49 (11)
C6—C7—S1	122.26 (12)	O2—O3—H3	97.2 (18)
C9—C8—C13	120.88 (17)	C8—S1—C7	91.72 (7)
C9—C8—S1	128.16 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.84 (1)	1.86 (1)	2.6962 (19)	173 (2)

Symmetry code: (i) −x, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₃S
M_r	275.31
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	295
a, b, c (Å)	7.8040 (5), 7.9800 (4), 10.2903 (5)
β (°)	99.458 (5)
V (Å³)	632.13 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Ruby, Gemi) diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.947, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	21595, 2555, 2162
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.068, 1.00
No. of reflections	2555
No. of parameters	176
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14
Absolute structure	Flack (1983), 1185 Friedel pairs
Absolute structure parameter	−0.05 (6)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND, (Brandenburg, 2001), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.841 (2)	1.859 (4)	2.6962 (19)	173 (2)

Symmetry code: (i) −x, y+1/2, −z.

Acknowledgements

The authors thank the Grant Agency of Slovak Republic, Grant Nos. 1/0429/11, 1/0679/11 and the Slovak Research and Development Agency under contract Nos. APVV-0797–11 and APVV-0204–10 for financial support for this research program.

References

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3327-o3328

doi:10.1107/S1600536812045394

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

(5S,11aS)-5-Hydro­per­­oxy-1,5,11,11a-tetra­hydro­[1]benzothieno[3,2-f]indol­izin-3(2H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(5S,11aS)-5-Hydroperoxy-1,5,11,11a-tetrahydro[1]benzothieno[3,2-f]indolizin-3(2H)-one