(11R,11aS)-11-Hydr-oxy-1,5,11,11a-tetra-hydro-1-benzothieno[2,3-f]indolizin-3(2H)-one.

The absolute configuration of the title compound, C(14)H(13)NO(2)S, was assigned from the synthesis and confirmed by the structure determination. The central six-membered ring of the indolizine system adopts an envelope conformation, the greatest deviation from the mean plane of the ring being 0.459 (2) Å for the N atom. The benzothieno system is planar [mean deviation = 0.009 (2) Å]. In the crystal structure, mol-ecules form chains parallel to the b axis via inter-molecular O-H⋯O hydrogen bonds.

Related literature

For related literature, see: Campagna et al. (1990 ▶); Camus et al. (2000 ▶); Gubin et al. (1992 ▶); Gupta et al. (2003 ▶); Malonne et al. (1998 ▶); Medda et al. (2003 ▶); Mitsumori et al. (2004 ▶); Nardelli (1983 ▶); Ostrander et al. (1988 ▶); Pearson & Guo (2001 ▶); Ruprecht et al. (1989 ▶); Sonnet et al. (2000 ▶); Teklu et al. (2005 ▶); Vlahovici et al. (2002 ▶); Vrábel et al. (2004 ▶); Šafář et al. (2008 ▶).

Experimental

Crystal data

C14H13NO2S

M = 259.31

Orthorhombic,

a = 7.6614 (1) Å

b = 11.7733 (2) Å

c = 13.0736 (2) Å

V = 1179.24 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 (2) K

0.50 × 0.30 × 0.28 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (Clark & Reid, 1995 ▶) T min = 0.867, T max = 0.941

32596 measured reflections

3149 independent reflections

2599 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.04

3149 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1259 Friedel pairs

Flack parameter: 0.01 (6)

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/S1600536808015456/bq2077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015456/bq2077Isup2.hkl

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

C14H13NO2S	F000 = 544
Mr = 259.31	Dx = 1.461 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 22009 reflections
a = 7.6614 (1) Å	θ = 3.1–26.4º
b = 11.7733 (2) Å	µ = 0.27 mm−1
c = 13.0736 (2) Å	T = 298 (2) K
V = 1179.24 (3) Å3	Block, white
Z = 4	0.50 × 0.30 × 0.28 mm

Oxford Diffraction Gemini R CCD diffractometer	3149 independent reflections
Radiation source: fine-focus sealed tube	2599 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
Detector resolution: 10.4340 pixels mm-1	θmax = 26.6º
T = 298(2) K	θmin = 3.1º
Rotation method data acquisition using ω and φ scans	h = −10→10
Absorption correction: analytical(Clark & Reid, 1995)	k = −16→15
Tmin = 0.867, Tmax = 0.941	l = −17→17
32596 measured reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0357P)2 + 0.2112P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.029	(Δ/σ)max < 0.001
wR(F2) = 0.076	Δρmax = 0.21 e Å−3
S = 1.04	Δρmin = −0.17 e Å−3
3149 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
165 parameters	Extinction coefficient: 0.0198 (16)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1259 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.01 (6)
Hydrogen site location: inferred from neighbouring sites

Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006)

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	0.1944 (2)	1.03675 (13)	0.20976 (13)	0.0455 (3)
C3	0.1497 (3)	1.05817 (14)	0.09913 (15)	0.0557 (4)
H3A	0.0504	1.1089	0.0935	0.067*
H3B	0.2480	1.0916	0.0634	0.067*
C4	0.1063 (3)	0.94225 (15)	0.05531 (14)	0.0582 (5)
H4A	0.2014	0.9147	0.0131	0.070*
H4B	0.0012	0.9459	0.0140	0.070*
C5	0.0789 (2)	0.86434 (13)	0.14788 (12)	0.0404 (3)
H5	−0.0462	0.8611	0.1634	0.048*
C6	0.14675 (19)	0.74306 (12)	0.13407 (10)	0.0378 (3)
H6	0.2456	0.7462	0.0866	0.045*
C7	0.21221 (18)	0.69361 (12)	0.23315 (10)	0.0354 (3)
C8	0.27062 (19)	0.57799 (12)	0.24570 (11)	0.0372 (3)
C9	0.2764 (2)	0.48925 (13)	0.17477 (12)	0.0440 (4)
H9	0.2386	0.5010	0.1080	0.053*
C10	0.3382 (2)	0.38453 (14)	0.20415 (15)	0.0509 (4)
H10	0.3420	0.3257	0.1567	0.061*
C11	0.3952 (2)	0.36526 (14)	0.30371 (15)	0.0517 (4)
H11	0.4352	0.2935	0.3221	0.062*
C12	0.3932 (2)	0.45092 (14)	0.37530 (14)	0.0475 (4)
H12	0.4322	0.4383	0.4417	0.057*
C13	0.33100 (19)	0.55722 (12)	0.34551 (11)	0.0397 (3)
C14	0.23124 (19)	0.75541 (12)	0.31979 (10)	0.0382 (3)
C15	0.1883 (3)	0.87867 (12)	0.33040 (11)	0.0455 (3)
H15A	0.0815	0.8878	0.3694	0.055*
H15B	0.2816	0.9177	0.3662	0.055*
N1	0.16682 (18)	0.92626 (10)	0.22933 (10)	0.0413 (3)
O1	0.24479 (19)	1.10666 (10)	0.27209 (11)	0.0614 (3)
O2	0.01482 (15)	0.67549 (10)	0.08796 (8)	0.0503 (3)
H2	−0.0601	0.6601	0.1306	0.076*
S1	0.31793 (6)	0.67853 (3)	0.42095 (3)	0.04613 (11)

	U11	U22	U33	U12	U13	U23
C2	0.0448 (8)	0.0367 (7)	0.0551 (9)	0.0070 (7)	0.0090 (8)	0.0030 (7)
C3	0.0607 (10)	0.0477 (8)	0.0586 (10)	0.0112 (8)	0.0067 (8)	0.0151 (8)
C4	0.0766 (12)	0.0550 (10)	0.0431 (9)	0.0100 (9)	−0.0054 (8)	0.0113 (7)
C5	0.0390 (7)	0.0453 (8)	0.0369 (7)	0.0062 (6)	0.0006 (6)	0.0016 (6)
C6	0.0422 (7)	0.0422 (7)	0.0290 (6)	0.0025 (6)	0.0025 (5)	0.0004 (5)
C7	0.0382 (7)	0.0377 (7)	0.0302 (6)	−0.0005 (6)	0.0023 (5)	0.0020 (5)
C8	0.0360 (7)	0.0384 (7)	0.0371 (7)	−0.0011 (5)	0.0027 (6)	0.0025 (5)
C9	0.0455 (9)	0.0424 (8)	0.0440 (8)	0.0016 (6)	0.0044 (7)	−0.0026 (6)
C10	0.0487 (9)	0.0423 (8)	0.0618 (10)	0.0047 (7)	0.0083 (8)	−0.0046 (7)
C11	0.0423 (8)	0.0401 (8)	0.0727 (11)	0.0050 (7)	0.0049 (8)	0.0099 (8)
C12	0.0417 (8)	0.0485 (9)	0.0523 (9)	0.0003 (7)	−0.0017 (7)	0.0131 (8)
C13	0.0393 (7)	0.0411 (7)	0.0389 (7)	−0.0018 (6)	0.0016 (6)	0.0050 (6)
C14	0.0466 (8)	0.0370 (7)	0.0309 (6)	−0.0023 (6)	0.0010 (6)	0.0016 (5)
C15	0.0620 (10)	0.0398 (7)	0.0348 (7)	0.0024 (7)	0.0027 (7)	−0.0025 (6)
N1	0.0494 (7)	0.0368 (6)	0.0377 (6)	0.0035 (5)	0.0022 (6)	0.0005 (5)
O1	0.0725 (8)	0.0396 (6)	0.0720 (8)	0.0007 (6)	0.0049 (7)	−0.0072 (6)
O2	0.0591 (7)	0.0554 (6)	0.0365 (5)	−0.0017 (6)	−0.0071 (5)	−0.0085 (6)
S1	0.0593 (2)	0.04554 (19)	0.03357 (17)	−0.00295 (18)	−0.00694 (17)	0.00349 (16)

C2—O1	1.221 (2)	C8—C9	1.398 (2)
C2—N1	1.3426 (19)	C8—C13	1.406 (2)
C2—C3	1.508 (2)	C9—C10	1.375 (2)
C3—C4	1.517 (3)	C9—H9	0.9300
C3—H3A	0.9700	C10—C11	1.392 (3)
C3—H3B	0.9700	C10—H10	0.9300
C4—C5	1.533 (2)	C11—C12	1.376 (3)
C4—H4A	0.9700	C11—H11	0.9300
C4—H4B	0.9700	C12—C13	1.395 (2)
C5—N1	1.456 (2)	C12—H12	0.9300
C5—C6	1.530 (2)	C13—S1	1.7385 (15)
C5—H5	0.9800	C14—C15	1.494 (2)
C6—O2	1.4206 (18)	C14—S1	1.7348 (14)
C6—C7	1.5061 (18)	C15—N1	1.4445 (18)
C6—H6	0.9800	C15—H15A	0.9700
C7—C14	1.3541 (19)	C15—H15B	0.9700
C7—C8	1.442 (2)	O2—H2	0.8200
O1—C2—N1	125.15 (16)	C9—C8—C7	129.79 (13)
O1—C2—C3	126.83 (15)	C13—C8—C7	111.83 (12)
N1—C2—C3	108.01 (14)	C10—C9—C8	119.72 (15)
C4—C3—C2	105.17 (13)	C10—C9—H9	120.1
C4—C3—H3A	110.7	C8—C9—H9	120.1
C2—C3—H3A	110.7	C9—C10—C11	121.02 (16)
C4—C3—H3B	110.7	C9—C10—H10	119.5
C2—C3—H3B	110.7	C11—C10—H10	119.5
H3A—C3—H3B	108.8	C12—C11—C10	120.88 (15)
C3—C4—C5	105.67 (14)	C12—C11—H11	119.6
C3—C4—H4A	110.6	C10—C11—H11	119.6
C5—C4—H4A	110.6	C11—C12—C13	118.14 (16)
C3—C4—H4B	110.6	C11—C12—H12	120.9
C5—C4—H4B	110.6	C13—C12—H12	120.9
H4A—C4—H4B	108.7	C12—C13—C8	121.85 (14)
N1—C5—C6	113.35 (12)	C12—C13—S1	126.76 (12)
N1—C5—C4	102.39 (13)	C8—C13—S1	111.39 (11)
C6—C5—C4	114.74 (13)	C7—C14—C15	125.15 (13)
N1—C5—H5	108.7	C7—C14—S1	113.49 (11)
C6—C5—H5	108.7	C15—C14—S1	121.35 (11)
C4—C5—H5	108.7	N1—C15—C14	108.47 (12)
O2—C6—C7	112.67 (12)	N1—C15—H15A	110.0
O2—C6—C5	109.32 (12)	C14—C15—H15A	110.0
C7—C6—C5	111.86 (12)	N1—C15—H15B	110.0
O2—C6—H6	107.6	C14—C15—H15B	110.0
C7—C6—H6	107.6	H15A—C15—H15B	108.4
C5—C6—H6	107.6	C2—N1—C15	122.16 (13)
C14—C7—C8	112.24 (12)	C2—N1—C5	114.75 (13)
C14—C7—C6	123.20 (12)	C15—N1—C5	121.84 (12)
C8—C7—C6	124.47 (12)	C6—O2—H2	109.5
C9—C8—C13	118.38 (13)	C14—S1—C13	91.04 (7)
O1—C2—C3—C4	176.43 (17)	C9—C8—C13—C12	−1.0 (2)
N1—C2—C3—C4	−4.46 (19)	C7—C8—C13—C12	179.72 (14)
C2—C3—C4—C5	15.15 (19)	C9—C8—C13—S1	178.57 (12)
C3—C4—C5—N1	−19.57 (18)	C7—C8—C13—S1	−0.73 (16)
C3—C4—C5—C6	−142.81 (14)	C8—C7—C14—C15	177.89 (15)
N1—C5—C6—O2	155.60 (12)	C6—C7—C14—C15	1.1 (2)
C4—C5—C6—O2	−87.26 (15)	C8—C7—C14—S1	−0.54 (16)
N1—C5—C6—C7	30.10 (17)	C6—C7—C14—S1	−177.34 (11)
C4—C5—C6—C7	147.24 (14)	C7—C14—C15—N1	−14.4 (2)
O2—C6—C7—C14	−132.48 (14)	S1—C14—C15—N1	163.94 (11)
C5—C6—C7—C14	−8.85 (19)	O1—C2—N1—C15	2.6 (3)
O2—C6—C7—C8	51.11 (18)	C3—C2—N1—C15	−176.58 (15)
C5—C6—C7—C8	174.74 (13)	O1—C2—N1—C5	169.96 (16)
C14—C7—C8—C9	−178.38 (16)	C3—C2—N1—C5	−9.17 (18)
C6—C7—C8—C9	−1.6 (2)	C14—C15—N1—C2	−153.70 (14)
C14—C7—C8—C13	0.81 (18)	C14—C15—N1—C5	39.8 (2)
C6—C7—C8—C13	177.57 (13)	C6—C5—N1—C2	142.58 (13)
C13—C8—C9—C10	0.8 (2)	C4—C5—N1—C2	18.41 (17)
C7—C8—C9—C10	179.94 (16)	C6—C5—N1—C15	−49.97 (19)
C8—C9—C10—C11	0.1 (3)	C4—C5—N1—C15	−174.13 (15)
C9—C10—C11—C12	−0.8 (3)	C7—C14—S1—C13	0.10 (12)
C10—C11—C12—C13	0.6 (2)	C15—C14—S1—C13	−178.39 (13)
C11—C12—C13—C8	0.3 (2)	C12—C13—S1—C14	179.90 (14)
C11—C12—C13—S1	−179.18 (12)	C8—C13—S1—C14	0.37 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	2.00	2.822 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	2.00	2.822 (2)	174

Symmetry code: (i) .