(8aS)-7,8,8a,9-Tetra-hydro-thieno[3,2-f]indolizin-6(4H)-one.

In the mol-ecular structure of the title compound, C(10)H(11)NOS, the central six-membered ring of the indolizine unit adopts an envelope conformation, the maximum deviations from the mean plane of the ring being 0.533 (2) Å. The fused thieno ring is nearly coplanar [mean deviation = 0.007 (2) Å]. The conformation of the fused oxopyrrolidine ring is close to that of a flat-envelope, with a maximum deviation of 0.339 (3) Å. The crystal structure is stabilized by C-H⋯O hydrogen bonds.

Related literature

For general applications of indolizine derivatives, see: Brandi et al. (1995 ▶); Campagna et al. (1990 ▶); Couture et al. (2000 ▶); Gubin et al. (1992 ▶); Gundersen et al. (2003 ▶); Gupta et al. (2003 ▶); Hema et al. (2003 ▶); Hempel et al. (1993 ▶); Jorgensen et al. (2000 ▶); Malonne et al. (1998 ▶); Marchalín et al. (2008 ▶); Medda et al. (2003 ▶); Nardelli (1983 ▶); Pearson & Guo (2001 ▶); Poty et al. (1994 ▶); Rosseels et al. (1982 ▶); Sonnet et al. (2000 ▶); Vlahovici et al. (2002 ▶); Vrábel et al. (2004 ▶); Švorc et al. (2007 ▶). For bond-length data, see: Brown & Corbridge (1954 ▶); Pedersen (1967 ▶).

Experimental

Crystal data

C10H11NOS

M = 193.26

Triclinic,

a = 6.37912 (16) Å

b = 8.3654 (3) Å

c = 9.0715 (3) Å

α = 84.180 (3)°

β = 78.611 (2)°

γ = 76.174 (3)°

V = 460.06 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 298 K

0.42 × 0.32 × 0.14 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (Clark & Reid, 1995 ▶) T min = 0.824, T max = 0.928

20197 measured reflections

2348 independent reflections

1918 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 1.06

2348 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536809007405/bg2239sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007405/bg2239Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H11NOS	Z = 2
Mr = 193.26	F(000) = 204
Triclinic, P1	Dx = 1.395 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.37912 (16) Å	Cell parameters from 12211 reflections
b = 8.3654 (3) Å	θ = 3.3–29.4°
c = 9.0715 (3) Å	µ = 0.31 mm−1
α = 84.180 (3)°	T = 298 K
β = 78.611 (2)°	Block, colourless
γ = 76.174 (3)°	0.42 × 0.32 × 0.14 mm
V = 460.06 (3) Å3

Oxford Diffraction Gemini R CCD diffractometer	2348 independent reflections
Radiation source: fine-focus sealed tube	1918 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 10.4340 pixels mm-1	θmax = 29.5°, θmin = 3.3°
Rotation method data acquisition using ω and φ scans	h = −8→8
Absorption correction: analytical (Clark & Reid, 1995)	k = −11→11
Tmin = 0.824, Tmax = 0.928	l = −12→12
20197 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.1103P] where P = (Fo2 + 2Fc2)/3
2348 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006)The absolute configuration could not be reliably determined for this compound using Mo-radiation, and has been assigned according to the synthesis.

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.

	x	y	z	Uiso*/Ueq
C2	0.1565 (3)	0.7697 (2)	1.25520 (17)	0.0449 (4)
C3	0.2584 (3)	0.6972 (2)	1.39075 (18)	0.0519 (4)
H3B	0.1863	0.6133	1.4449	0.062*
H3A	0.2485	0.7821	1.4588	0.062*
C4	0.4980 (3)	0.6222 (2)	1.32515 (17)	0.0482 (4)
H4B	0.5952	0.6373	1.3899	0.058*
H4A	0.5196	0.5054	1.3120	0.058*
C5	0.5387 (2)	0.7177 (2)	1.17316 (16)	0.0411 (3)
H5A	0.5841	0.8180	1.1880	0.049*
C6	0.7046 (2)	0.6242 (2)	1.05152 (16)	0.0437 (3)
H6B	0.8519	0.6205	1.0671	0.052*
H6A	0.6866	0.5118	1.0551	0.052*
C7	0.6721 (2)	0.70843 (18)	0.90130 (16)	0.0397 (3)
C8	0.6992 (3)	0.8129 (2)	0.63501 (19)	0.0548 (4)
H8A	0.7385	0.8395	0.5328	0.066*
C9	0.4964 (3)	0.8674 (2)	0.71745 (17)	0.0481 (4)
H9A	0.3807	0.9362	0.6779	0.058*
C10	0.4802 (2)	0.80769 (17)	0.87139 (16)	0.0370 (3)
C11	0.2797 (2)	0.84994 (19)	0.99057 (16)	0.0413 (3)
H11B	0.2413	0.9680	1.0020	0.050*
H11A	0.1577	0.8193	0.9603	0.050*
N1	0.31810 (18)	0.76400 (15)	1.13355 (13)	0.0369 (3)
O1	−0.03879 (19)	0.82620 (19)	1.25376 (15)	0.0653 (4)
S1	0.87330 (7)	0.68901 (6)	0.74263 (5)	0.05585 (18)

	U11	U22	U33	U12	U13	U23
C2	0.0358 (8)	0.0559 (9)	0.0399 (8)	−0.0084 (6)	−0.0014 (6)	−0.0036 (6)
C3	0.0459 (9)	0.0707 (11)	0.0334 (7)	−0.0092 (8)	0.0004 (6)	−0.0006 (7)
C4	0.0413 (8)	0.0636 (10)	0.0350 (7)	−0.0049 (7)	−0.0079 (6)	0.0042 (7)
C5	0.0320 (7)	0.0511 (8)	0.0376 (7)	−0.0046 (6)	−0.0068 (6)	−0.0004 (6)
C6	0.0346 (7)	0.0518 (8)	0.0373 (7)	0.0008 (6)	−0.0045 (6)	0.0026 (6)
C7	0.0367 (7)	0.0445 (8)	0.0326 (7)	−0.0041 (6)	−0.0008 (5)	−0.0010 (5)
C8	0.0668 (11)	0.0585 (10)	0.0321 (7)	−0.0093 (8)	−0.0013 (7)	0.0036 (7)
C9	0.0583 (10)	0.0458 (8)	0.0356 (7)	−0.0038 (7)	−0.0100 (7)	0.0035 (6)
C10	0.0392 (7)	0.0362 (7)	0.0335 (7)	−0.0055 (5)	−0.0056 (5)	−0.0007 (5)
C11	0.0356 (7)	0.0445 (8)	0.0385 (7)	−0.0007 (6)	−0.0070 (6)	0.0028 (6)
N1	0.0290 (6)	0.0456 (6)	0.0328 (6)	−0.0039 (5)	−0.0047 (4)	0.0009 (5)
O1	0.0320 (6)	0.0977 (10)	0.0558 (7)	−0.0034 (6)	0.0003 (5)	0.0010 (7)
S1	0.0463 (3)	0.0700 (3)	0.0387 (2)	−0.00116 (19)	0.00624 (17)	−0.00050 (18)

C2—O1	1.2244 (19)	C6—H6B	0.9700
C2—N1	1.3494 (19)	C6—H6A	0.9700
C2—C3	1.509 (2)	C7—C10	1.364 (2)
C3—C4	1.531 (2)	C7—S1	1.7216 (15)
C3—H3B	0.9700	C8—C9	1.359 (3)
C3—H3A	0.9700	C8—S1	1.7127 (19)
C4—C5	1.530 (2)	C8—H8A	0.9300
C4—H4B	0.9700	C9—C10	1.4271 (19)
C4—H4A	0.9700	C9—H9A	0.9300
C5—N1	1.4730 (18)	C10—C11	1.4983 (19)
C5—C6	1.506 (2)	C11—N1	1.4530 (18)
C5—H5A	0.9800	C11—H11B	0.9700
C6—C7	1.498 (2)	C11—H11A	0.9700
O1—C2—N1	124.92 (15)	C5—C6—H6A	109.9
O1—C2—C3	126.64 (15)	H6B—C6—H6A	108.3
N1—C2—C3	108.44 (13)	C10—C7—C6	124.86 (13)
C2—C3—C4	104.44 (13)	C10—C7—S1	111.24 (11)
C2—C3—H3B	110.9	C6—C7—S1	123.89 (11)
C4—C3—H3B	110.9	C9—C8—S1	111.60 (12)
C2—C3—H3A	110.9	C9—C8—H8A	124.2
C4—C3—H3A	110.9	S1—C8—H8A	124.2
H3B—C3—H3A	108.9	C8—C9—C10	112.69 (15)
C5—C4—C3	103.88 (13)	C8—C9—H9A	123.7
C5—C4—H4B	111.0	C10—C9—H9A	123.7
C3—C4—H4B	111.0	C7—C10—C9	112.41 (14)
C5—C4—H4A	111.0	C7—C10—C11	122.46 (13)
C3—C4—H4A	111.0	C9—C10—C11	125.11 (13)
H4B—C4—H4A	109.0	N1—C11—C10	110.65 (12)
N1—C5—C6	111.65 (12)	N1—C11—H11B	109.5
N1—C5—C4	102.22 (12)	C10—C11—H11B	109.5
C6—C5—C4	115.73 (14)	N1—C11—H11A	109.5
N1—C5—H5A	109.0	C10—C11—H11A	109.5
C6—C5—H5A	109.0	H11B—C11—H11A	108.1
C4—C5—H5A	109.0	C2—N1—C11	122.02 (12)
C7—C6—C5	109.13 (12)	C2—N1—C5	112.77 (12)
C7—C6—H6B	109.9	C11—N1—C5	121.72 (12)
C5—C6—H6B	109.9	C8—S1—C7	92.04 (8)
C7—C6—H6A	109.9
O1—C2—C3—C4	171.40 (18)	C7—C10—C11—N1	−3.3 (2)
N1—C2—C3—C4	−9.31 (19)	C9—C10—C11—N1	178.30 (14)
C2—C3—C4—C5	23.40 (19)	O1—C2—N1—C11	10.3 (3)
C3—C4—C5—N1	−28.18 (17)	C3—C2—N1—C11	−168.98 (14)
C3—C4—C5—C6	−149.74 (14)	O1—C2—N1—C5	169.56 (17)
N1—C5—C6—C7	44.61 (18)	C3—C2—N1—C5	−9.74 (18)
C4—C5—C6—C7	160.97 (13)	C10—C11—N1—C2	−173.84 (13)
C5—C6—C7—C10	−24.2 (2)	C10—C11—N1—C5	28.76 (19)
C5—C6—C7—S1	156.95 (12)	C6—C5—N1—C2	148.74 (14)
S1—C8—C9—C10	−0.2 (2)	C4—C5—N1—C2	24.42 (17)
C6—C7—C10—C9	−178.47 (14)	C6—C5—N1—C11	−51.94 (19)
S1—C7—C10—C9	0.54 (17)	C4—C5—N1—C11	−176.27 (13)
C6—C7—C10—C11	2.9 (2)	C9—C8—S1—C7	0.39 (15)
S1—C7—C10—C11	−178.07 (11)	C10—C7—S1—C8	−0.53 (13)
C8—C9—C10—C7	−0.3 (2)	C6—C7—S1—C8	178.49 (15)
C8—C9—C10—C11	178.31 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.93	2.60	3.379 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.93	2.60	3.379 (2)	142

Symmetry code: (i) .