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

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

doi:10.1107/S1600536808015456

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o1164-o1165

doi:10.1107/S1600536808015456

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

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

^aInstitute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, ^bInstitute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute 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 17 April 2008; accepted 22 May 2008; online 30 May 2008)

The absolute configuration of the title compound, C₁₄H₁₃NO₂S, 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, molecules form chains parallel to the b axis via intermolecular 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_r = 259.31
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.076
S = 1.04
3149 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 1259 Friedel pairs
Flack parameter: 0.01 (6)

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) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536808015456/bq2077sup1.cif

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

checkCIF report

Comment top

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. They have also shown to be calcium entry blockers (Gupta et al., 2003) and potent antioxidants inhibiting lipid peroxidation in vitro (Teklu et al., 2005). As such, indolizines are important synthetic targets in view of developing new pharmaceuticals for the treatment of cancer (Ostrander et al., 1988), cardiovascular diseases (Gubin et al., 1992) and HIV infections (Ruprecht et al., 1989). Polycyclic indolizine derivatives have been found to have high-efficiency long-wavelength fluorescence quantum yield (Vlahovici et al., 2002). The synthesis of polycyclic indolizine derivatives has recently attracted much research interest in the search for new opto-electric materials (Mitsumori et al., 2004). 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 [absolute structure parameter 0.01 (6) (Flack, 1983)] and assigned consistent with the starting material. The expected stereochemistry of atoms C5 and C6 was confirmed as S and R, respectively (Fig. 1). The central N-heterocyclic ring is not planar and adopts an envelope conformation (Nardelli, 1983). A calculation of least-squares planes shows that this ring is puckered in such a manner that the five atoms C5, C6, C7, C14 and C15 are planar to within 0.061 (3) Å, while atom N1 is displaced from this plane with out-of-plane displacement of 0.459 (2) Å. The pyrrolidin-2-one ring is distorted towards a flat-envelope conformation, with atom C5 on the flap. Atom C5 is 0.291 (2)Å from the mean plane defined by atoms N1, C2, C3 and C4. The molecule as a whole is nonplanar but consist of two approximately planar segments, C5, C6, C7, C8, C9, C10, C11, C12, C13, S1, C14, C15 [r.m.s. deviation 0.086 (2) Å] and N1, C2, O1, C3, C4 [r.m.s. deviation 0.046 (3) Å] with dihedral angle 27.0 (1)°. Atom N1 is sp²-hybridized, as evidenced by the sum of the valence angles around it (358.8°). 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 of (I) into infinite chains, which run parallel to the b axis (Fig. 2 and Table 2) and help to stabilize the crystal structure of the compound. The bond lengths of the carbonyl group C2=O1 is 1.221 (2)Å somewhat longer than typical carbonyl bonds. This may be due to the fact that atom O1 participates in intermolecular hydrogen bond. The bond lengths and angles in the indolizine ring system are comparable with those in related structures (Camus, et al., 2000; Vrábel, et al., 2004).

Related literature top

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 top

The title compound (11R,11aS)-11-hydroxy-1,5,11,11a-tetrahydro[1] benzothieno[2,3-f]indolizin-3(2H)-one was prepared according literature procedures of Šafář, et al. (2008).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); 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).

Figures top

	Fig. 1. Molecular structure of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of the compound (I). Dashed lines indicate hydrogen bonds.

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

Crystal data top

C₁₄H₁₃NO₂S	F(000) = 544
M_r = 259.31	D_x = 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 = 3.1–26.4°
b = 11.7733 (2) Å	µ = 0.27 mm⁻¹
c = 13.0736 (2) Å	T = 298 K
V = 1179.24 (3) Å³	Block, white
Z = 4	0.50 × 0.30 × 0.28 mm

Data collection top

Oxford Diffraction Gemini R CCD diffractometer	3149 independent reflections
Radiation source: fine-focus sealed tube	2599 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 10.4340 pixels mm^-1	θ_max = 26.6°, θ_min = 3.1°
Rotation method data acquisition using ω and ϕ scans	h = −10→10
Absorption correction: analytical (Clark & Reid, 1995)	k = −16→15
T_min = 0.867, T_max = 0.941	l = −17→17
32596 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0357P)² + 0.2112P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.076	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.21 e Å⁻³
3149 reflections	Δρ_min = −0.17 e Å⁻³
165 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	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	Absolute structure parameter: 0.01 (6)

Crystal data top

C₁₄H₁₃NO₂S	V = 1179.24 (3) Å³
M_r = 259.31	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.6614 (1) Å	µ = 0.27 mm⁻¹
b = 11.7733 (2) Å	T = 298 K
c = 13.0736 (2) Å	0.50 × 0.30 × 0.28 mm

Data collection top

Oxford Diffraction Gemini R CCD diffractometer	3149 independent reflections
Absorption correction: analytical (Clark & Reid, 1995)	2599 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.941	R_int = 0.019
32596 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.076	Δρ_max = 0.21 e Å⁻³
S = 1.04	Δρ_min = −0.17 e Å⁻³
3149 reflections	Absolute structure: Flack (1983), 1259 Friedel pairs
165 parameters	Absolute structure parameter: 0.01 (6)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂S
M_r	259.31
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.6614 (1), 11.7733 (2), 13.0736 (2)
V (Å³)	1179.24 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.50 × 0.30 × 0.28

Data collection
Diffractometer	Oxford Diffraction Gemini R CCD diffractometer
Absorption correction	Analytical (Clark & Reid, 1995)
T_min, T_max	0.867, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	32596, 3149, 2599
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.076, 1.04
No. of reflections	3149
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17
Absolute structure	Flack (1983), 1259 Friedel pairs
Absolute structure parameter	0.01 (6)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2001), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	2.00	2.822 (2)	174.1

Symmetry code: (i) −x, y−1/2, −z+1/2.

Acknowledgements

The authors thank the Grant Agency of the Slovak Republic (grant Nos. 1/0817/08 and 1/0161/08) as well as the Structural Funds, Interreg IIIA, for financial support in the purchase of the diffractometer.

References

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Volume 64| Part 6| June 2008| Pages o1164-o1165

doi:10.1107/S1600536808015456

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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