(3aR,4S,7R,7aS)-2-Phenyl-4-propyl-3a,4,7,7a-tetra­hydro-1H-4,7-epithio­iso­indole-1,3-dione 8-oxide

Demircan, A.; Şahin, E.; Beyazova, G.; Karaaslan, M.; Hökelek, T.

doi:10.1107/S1600536811012876

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1085-o1086

doi:10.1107/S1600536811012876

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(3aR,4S,7R,7aS)-2-Phenyl-4-propyl-3a,4,7,7a-tetrahydro-1H-4,7-epithioisoindole-1,3-dione 8-oxide

Aydın Demircan,^a Ertan Şahin,^b Gözde Beyazova,^a Muhsin Karaaslan ^c and Tuncer Hökelek ^d ^*

^aDepartment of Chemistry, Niğde University, 51100 Niğde, Turkey, ^bDepartment of Chemistry, Atatürk University, 25240 Erzurum, Turkey, ^cDepartment of Chemistry, Aksaray University, 68100 Aksaray, Turkey, and ^dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 23 March 2011; accepted 6 April 2011; online 13 April 2011)

In the tetrahydroisoindole moiety of the title compound, C₁₇H₁₇NO₃S, the six-membered ring assumes a boat configuration and the –S=O group bridges the prow and stern of the boat. The phenyl ring is oriented at a dihedral angle of 83.2 (1)° with respect to the pyrrole ring. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into a three-dimensional network. A weak C—H⋯π interaction involving the phenyl ring is also found. The crystal studied was an inversion twin.

Related literature

For background to the thiophenen system, see: Lert & Trindle (1971 ). For the conditions of cycloaddition reactions of thiophene, see: Al-Omran et al. (1996 ); Kuhn & Gollnick (1972 ); Kotsuki et al. (1978 ); Thiemann et al. (1995 ). For the biological activity of some thiophene 1,1-dioxide derivatives, see: Thiemann et al. (2009 ). For thiophene s-oxides with alkyl groups at positions 2,3,4 and 5, see: Rajappa (1984 ). For related structures, see: Arslan & Demircan (2007 ); Koşar et al. (2006 ).

Experimental

Crystal data

C₁₇H₁₇NO₃S
M_r = 315.39
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.7712 (3) Å
b = 10.8413 (3) Å
c = 18.9762 (4) Å
V = 1598.74 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 294 K
0.30 × 0.25 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.807, T_max = 0.865
34450 measured reflections
3279 independent reflections
2686 reflections with I > 2σ(I)
R_int = 0.088

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.108
S = 1.08
3279 reflections
210 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1379 Friedel pairs
Flack parameter: 0.37 (9)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.95 (2)	2.51 (3)	3.326 (4)	144 (2)
C17—H17⋯O3ⁱⁱ	0.93	2.57	3.315 (3)	137
C7—H7⋯Cg1ⁱⁱⁱ	0.98	2.77	3.693 (3)	157
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) x-1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); 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 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012876/xu5179sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012876/xu5179Isup2.hkl

checkCIF report

Comment top

Thiophene behaves as the least reactive diene among all aromatic five-membered heterocycles; the presence of 3d orbitals on sulfur contributes to the resonance stability of the thiophene system (Lert & Trindle, 1971). Cycloaddition reactions of thiophene also have limitations therefore its 4 + 2 cycloaddition can occur under following conditions; use of highly reactive dienophiles (Thiemann et al., 1995), enhance electron density on the thiophene by having substituent at position 2 or 5 (Al-Omran et al., 1996), high reaction temperature (Kuhn & Gollnick, 1972) or use of high pressure (Kotsuki et al., 1978). However, the number of publications dealing with the chemistry of thiophene dioxide based new materials, namely, semiconductor organic transistors and light diodes first designed about 13 years ago. New data on the biological activities of some thiophene 1,1-dioxide derivatives were observed in recent years (Thiemann et al., 2009).

Thiophene s-oxides are derivatives of thiophene, which belong to an important group of five-membered heterocyclic compounds having non-aromatic character. Thiophene s-oxides with alkyl groups at positions 2,3,4 and 5 have been the subject of extensive studies in recent past (Rajappa, 1984). Owing to the unique structure combined with high reactivity, they can be used to prepare various heterocyclic systems; therefore, these compounds are useful building blocks in synthetic organic chemistry. In continuation of our research program and following our previous interest in the sytheses of fused heterocyclic compounds using furan (Arslan & Demircan, 2007; Koşar et al., 2006), it has been found that mono alkylated thiophene at position 2 will lead to an excellent building block for the synthesis of the title compound.

The title compound contains two non-planar five- and six-membered rings, which has a pyrrole (C1/N2/C3/C3a/C7a) ring (B) on one side and a propyl moiety at position 4. It also contains a phenyl (C12-C17) ring (A) bonded to the pyrrole ring (B) at position 2. The angles C4-C5-C6 [111.4 (3)°] and C5-C6-C7 [111.1 (3)°] about the double bond have an average value of 111.3 (3)°. The dihedral angles between planes A, B, C (C3a/C4/C7a C7), D (C4-C7) and E (C4/S8/C7) are as follows: A/B = 83.2 (1)°, B/C = 61.9 (1)°, C/D = 60.6 (1)°, C/E = 58.8 (1)° and D/E = 60.7 (1)°.

In the crystal, intermolecular C—H···O hydrogen bonds link the molecules to form a three-dimensional network (Table 1 and Fig. 2). There also exist a weak C—H···π interaction involving the phenyl ring A (C12-C17) (Table 1).

Related literature top

For background to the thiophenen system, see: Lert & Trindle (1971). For the conditions of cycloaddition reactions of thiophene, see: Al-Omran et al. (1996); Kuhn & Gollnick (1972); Kotsuki et al. (1978); Thiemann et al. (1995). For the biological activity of some thiophene 1,1-dioxide derivatives, see: Thiemann et al. (2009). For thiophene s-oxides with alkyl groups at positions 2,3,4 and 5, see: Rajappa (1984). For related structures, see: Arslan & Demircan (2007); Koşar et al. (2006).

Experimental top

For the preparation of the title compound, BF₃.Et₂O (6.1 ml, 47.75 mmol) was added slowly to a solution of 2-propylthiophene (1.00 g, 7.90 mmol) and N-phenylmaleimide (2.06 g, 11.90 mmol) in dry dichloromethane (DCM) (40 ml) under an inert atmosphere at 253 K. The reaction mixture was stirred for 10 min at 253 K, and then a solution of meta chloroperbenzoic acid (m-CPBA) (2.05 g, 11.90 mmol) in dry DCM (40 ml) was added slowly. The reaction mixture was stirred for 2 h at 253 K, and then the suspension was poured into a mixture of aqueous NaHCO₃ solution (80 ml) and DCM (50 ml) and stirred at room temperature for 20 min. The organic phase was separated, and the aqueous phase was extracted with DCM (3 x 25 ml). The combined organic phase was washed with water and brine, and then dried over anhydrous MgSO₄. After removal of the solvent in vacuo, the residue was chromatographed on silica gel to give the title compound as colorless crystals.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A view of the crystal packing of the title compound. The C-H···O hydrogen bonds are shown as dashed lines [H-atoms not involved in hydrogen bonding have been omitted for clarity].

(3aR,4S,7R,7aS)-2-Phenyl-4-propyl-3a,4,7,7a-tetrahydro-1H-4,7-epithioisoindole-1,3-dione 8-oxide top

Crystal data top

C₁₇H₁₇NO₃S	F(000) = 664
M_r = 315.39	D_x = 1.310 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6907 reflections
a = 7.7712 (3) Å	θ = 2.2–26.4°
b = 10.8413 (3) Å	µ = 0.21 mm⁻¹
c = 18.9762 (4) Å	T = 294 K
V = 1598.74 (8) Å³	Block, colorless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3279 independent reflections
Radiation source: fine-focus sealed tube	2686 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.088
ω scans	θ_max = 26.4°, θ_min = 2.2°
Absorption correction: multi-scan (Blessing, 1995)	h = −9→9
T_min = 0.807, T_max = 0.865	k = −13→13
34450 measured reflections	l = −23→23

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.047	w = 1/[σ²(F_o²) + (0.0453P)² + 0.1086P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.108	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.20 e Å⁻³
3279 reflections	Δρ_min = −0.22 e Å⁻³
210 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.018 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1379 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.37 (9)

Crystal data top

C₁₇H₁₇NO₃S	V = 1598.74 (8) Å³
M_r = 315.39	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.7712 (3) Å	µ = 0.21 mm⁻¹
b = 10.8413 (3) Å	T = 294 K
c = 18.9762 (4) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3279 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	2686 reflections with I > 2σ(I)
T_min = 0.807, T_max = 0.865	R_int = 0.088
34450 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.108	Δρ_max = 0.20 e Å⁻³
S = 1.08	Δρ_min = −0.22 e Å⁻³
3279 reflections	Absolute structure: Flack (1983), 1379 Friedel pairs
210 parameters	Absolute structure parameter: 0.37 (9)
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	−0.0424 (3)	0.0571 (2)	0.16742 (11)	0.0742 (6)
O2	0.3289 (2)	0.35385 (18)	0.09320 (10)	0.0708 (6)
O3	−0.3050 (2)	0.40176 (16)	0.00144 (9)	0.0633 (5)
C1	0.0032 (3)	0.1488 (3)	0.13751 (14)	0.0553 (6)
N2	0.1690 (3)	0.1987 (2)	0.14224 (10)	0.0528 (5)
C3	0.1923 (3)	0.3011 (2)	0.10005 (12)	0.0526 (6)
C3A	0.0230 (3)	0.3335 (2)	0.06695 (13)	0.0488 (6)
H3A	0.0324	0.3349	0.0155	0.059*
C4	−0.0495 (3)	0.4576 (2)	0.09505 (13)	0.0541 (6)
C5	−0.0650 (4)	0.4517 (3)	0.17396 (15)	0.0654 (8)
H5	−0.003 (3)	0.503 (2)	0.2053 (14)	0.060 (8)*
C6	−0.1750 (4)	0.3652 (3)	0.19369 (15)	0.0659 (8)
H6	−0.216 (4)	0.346 (3)	0.2393 (16)	0.083 (9)*
C7	−0.2475 (3)	0.2998 (2)	0.13186 (13)	0.0578 (7)
H7	−0.3499	0.2498	0.1414	0.069*
C7A	−0.1015 (3)	0.2327 (2)	0.09100 (12)	0.0509 (6)
H7A	−0.1479	0.1875	0.0505	0.061*
S8	−0.28413 (8)	0.43745 (6)	0.07643 (3)	0.0564 (2)
C9	0.0304 (4)	0.5709 (3)	0.06204 (17)	0.0716 (8)
H9A	0.1537	0.5675	0.0698	0.086*
H9B	0.0113	0.5671	0.0116	0.086*
C10	−0.0343 (5)	0.6940 (3)	0.0883 (2)	0.1081 (13)
H10A	−0.1584	0.6967	0.0831	0.130*
H10B	−0.0081	0.7014	0.1381	0.130*
C11	0.0429 (8)	0.8016 (4)	0.0500 (3)	0.176 (3)
H11A	−0.0063	0.8768	0.0675	0.264*
H11B	0.0192	0.7943	0.0005	0.264*
H11C	0.1650	0.8026	0.0574	0.264*
C12	0.3072 (3)	0.1422 (2)	0.18063 (14)	0.0580 (7)
C13	0.3496 (4)	0.1844 (3)	0.24562 (15)	0.0729 (9)
H13	0.2888	0.2488	0.2663	0.087*
C14	0.4881 (5)	0.1281 (4)	0.2808 (2)	0.0951 (12)
H14	0.5197	0.1554	0.3255	0.114*
C15	0.5753 (5)	0.0350 (4)	0.2504 (3)	0.1005 (14)
H15	0.6669	−0.0010	0.2743	0.121*
C16	0.5321 (5)	−0.0070 (4)	0.1856 (2)	0.0974 (12)
H16	0.5939	−0.0710	0.1651	0.117*
C17	0.3949 (4)	0.0460 (3)	0.15000 (16)	0.0732 (8)
H17	0.3626	0.0168	0.1059	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0578 (11)	0.0808 (14)	0.0841 (14)	−0.0097 (11)	−0.0041 (10)	0.0270 (12)
O2	0.0467 (10)	0.0775 (13)	0.0883 (14)	−0.0098 (9)	0.0005 (9)	0.0129 (11)
O3	0.0654 (12)	0.0712 (12)	0.0533 (10)	0.0027 (10)	−0.0088 (9)	−0.0030 (9)
C1	0.0522 (15)	0.0627 (17)	0.0509 (14)	−0.0031 (12)	0.0019 (12)	0.0021 (13)
N2	0.0457 (11)	0.0591 (12)	0.0537 (12)	−0.0010 (9)	−0.0012 (9)	0.0057 (10)
C3	0.0486 (15)	0.0587 (14)	0.0506 (13)	0.0003 (13)	0.0024 (11)	−0.0015 (11)
C3A	0.0463 (13)	0.0526 (14)	0.0476 (13)	0.0001 (10)	0.0013 (11)	0.0006 (11)
C4	0.0499 (14)	0.0552 (15)	0.0573 (15)	−0.0011 (12)	0.0010 (12)	−0.0058 (12)
C5	0.0577 (16)	0.081 (2)	0.0572 (16)	0.0093 (16)	−0.0064 (14)	−0.0204 (15)
C6	0.0559 (17)	0.090 (2)	0.0521 (16)	0.0140 (16)	0.0059 (13)	−0.0032 (15)
C7	0.0482 (15)	0.0675 (16)	0.0578 (15)	−0.0004 (12)	0.0037 (12)	0.0069 (13)
C7A	0.0458 (13)	0.0571 (14)	0.0499 (14)	−0.0020 (11)	−0.0026 (11)	0.0012 (11)
S8	0.0511 (4)	0.0604 (4)	0.0576 (4)	0.0037 (3)	−0.0014 (3)	−0.0029 (3)
C9	0.0703 (18)	0.0600 (17)	0.084 (2)	−0.0091 (15)	0.0010 (15)	−0.0013 (16)
C10	0.111 (3)	0.0577 (19)	0.156 (4)	−0.0059 (19)	0.021 (3)	−0.007 (2)
C11	0.196 (6)	0.061 (3)	0.272 (7)	−0.023 (3)	0.070 (5)	0.004 (3)
C12	0.0467 (14)	0.0694 (17)	0.0579 (15)	−0.0037 (13)	−0.0035 (12)	0.0137 (13)
C13	0.0675 (18)	0.090 (2)	0.0611 (17)	−0.0115 (17)	−0.0119 (14)	0.0085 (15)
C14	0.081 (3)	0.129 (3)	0.075 (2)	−0.035 (2)	−0.026 (2)	0.033 (2)
C15	0.062 (2)	0.127 (4)	0.112 (3)	0.000 (2)	−0.017 (2)	0.057 (3)
C16	0.076 (2)	0.113 (3)	0.103 (3)	0.025 (2)	−0.004 (2)	0.027 (2)
C17	0.0665 (18)	0.079 (2)	0.0737 (19)	0.0133 (17)	−0.0027 (15)	0.0094 (17)

Geometric parameters (Å, º) top

O1—C1	1.198 (3)	S8—C7	1.848 (3)
O2—C3	1.213 (3)	C9—C10	1.511 (4)
C1—C7A	1.506 (3)	C9—H9A	0.9700
N2—C1	1.401 (3)	C9—H9B	0.9700
N2—C3	1.380 (3)	C10—C11	1.500 (6)
N2—C12	1.435 (3)	C10—H10A	0.9700
C3A—C3	1.500 (3)	C10—H10B	0.9700
C3A—C4	1.553 (3)	C11—H11A	0.9600
C3A—C7A	1.529 (3)	C11—H11B	0.9600
C3A—H3A	0.9800	C11—H11C	0.9600
C4—C5	1.504 (4)	C12—C13	1.356 (4)
C4—C9	1.511 (4)	C12—C17	1.375 (4)
C5—H5	0.95 (3)	C13—C14	1.406 (5)
C6—C5	1.323 (5)	C13—H13	0.9300
C6—H6	0.95 (3)	C14—H14	0.9300
C7—C6	1.482 (4)	C15—C14	1.346 (5)
C7—C7A	1.555 (3)	C15—C16	1.353 (6)
C7—H7	0.9800	C15—H15	0.9300
C7A—H7A	0.9800	C16—H16	0.9300
S8—O3	1.4836 (18)	C17—C16	1.387 (4)
S8—C4	1.871 (3)	C17—H17	0.9300

O1—C1—N2	124.2 (2)	O3—S8—C4	108.56 (11)
O1—C1—C7A	128.2 (2)	O3—S8—C7	110.62 (11)
N2—C1—C7A	107.5 (2)	C7—S8—C4	80.60 (11)
C1—N2—C12	123.8 (2)	C4—C9—H9A	108.2
C3—N2—C1	113.2 (2)	C4—C9—H9B	108.2
C3—N2—C12	122.7 (2)	C10—C9—C4	116.4 (3)
O2—C3—N2	123.8 (2)	C10—C9—H9A	108.2
O2—C3—C3A	127.8 (2)	C10—C9—H9B	108.2
N2—C3—C3A	108.4 (2)	H9A—C9—H9B	107.3
C3—C3A—C4	112.2 (2)	C9—C10—H10A	108.9
C3—C3A—C7A	105.22 (19)	C9—C10—H10B	108.9
C3—C3A—H3A	110.8	C11—C10—C9	113.2 (3)
C4—C3A—H3A	110.8	C11—C10—H10A	108.9
C7A—C3A—C4	106.71 (19)	C11—C10—H10B	108.9
C7A—C3A—H3A	110.8	H10A—C10—H10B	107.7
C3A—C4—S8	100.79 (16)	C10—C11—H11A	109.5
C5—C4—S8	96.01 (18)	C10—C11—H11B	109.5
C5—C4—C3A	109.5 (2)	C10—C11—H11C	109.5
C5—C4—C9	118.7 (2)	H11A—C11—H11B	109.5
C9—C4—S8	114.65 (19)	H11A—C11—H11C	109.5
C9—C4—C3A	114.4 (2)	H11B—C11—H11C	109.5
C4—C5—H5	124.0 (16)	C13—C12—N2	120.0 (3)
C6—C5—C4	111.4 (3)	C13—C12—C17	121.3 (3)
C6—C5—H5	124.7 (15)	C17—C12—N2	118.7 (2)
C5—C6—C7	111.1 (3)	C12—C13—C14	118.2 (3)
C5—C6—H6	129.2 (19)	C12—C13—H13	120.9
C7—C6—H6	119.5 (19)	C14—C13—H13	120.9
S8—C7—H7	115.3	C13—C14—H14	119.8
C6—C7—S8	97.05 (19)	C15—C14—C13	120.4 (4)
C6—C7—C7A	110.0 (2)	C15—C14—H14	119.8
C6—C7—H7	115.3	C14—C15—C16	121.2 (4)
C7A—C7—S8	101.92 (16)	C14—C15—H15	119.4
C7A—C7—H7	115.3	C16—C15—H15	119.4
C1—C7A—C3A	105.4 (2)	C15—C16—C17	119.6 (4)
C1—C7A—C7	112.6 (2)	C15—C16—H16	120.2
C1—C7A—H7A	110.9	C17—C16—H16	120.2
C3A—C7A—C7	106.0 (2)	C12—C17—C16	119.3 (3)
C3A—C7A—H7A	110.9	C12—C17—H17	120.3
C7—C7A—H7A	110.9	C16—C17—H17	120.3

O1—C1—C7A—C3A	−179.5 (3)	C3A—C4—C5—C6	−62.6 (3)
O1—C1—C7A—C7	65.4 (4)	C9—C4—C5—C6	163.5 (3)
N2—C1—C7A—C3A	2.2 (3)	S8—C4—C9—C10	65.0 (3)
N2—C1—C7A—C7	−112.9 (2)	C3A—C4—C9—C10	−179.3 (3)
C3—N2—C1—O1	176.9 (3)	C5—C4—C9—C10	−47.5 (4)
C3—N2—C1—C7A	−4.8 (3)	C7—C6—C5—C4	0.7 (3)
C12—N2—C1—O1	3.5 (4)	S8—C7—C6—C5	−42.9 (3)
C12—N2—C1—C7A	−178.1 (2)	C7A—C7—C6—C5	62.5 (3)
C1—N2—C3—O2	−175.5 (2)	S8—C7—C7A—C1	156.02 (18)
C1—N2—C3—C3A	5.3 (3)	S8—C7—C7A—C3A	41.3 (2)
C12—N2—C3—O2	−2.1 (4)	C6—C7—C7A—C1	53.9 (3)
C12—N2—C3—C3A	178.8 (2)	C6—C7—C7A—C3A	−60.8 (3)
C1—N2—C12—C13	−100.8 (3)	O3—S8—C4—C3A	−51.85 (18)
C1—N2—C12—C17	79.6 (3)	O3—S8—C4—C5	−163.06 (17)
C3—N2—C12—C13	86.5 (3)	O3—S8—C4—C9	71.5 (2)
C3—N2—C12—C17	−93.1 (3)	C7—S8—C4—C3A	56.87 (16)
C4—C3A—C3—O2	−67.0 (3)	C7—S8—C4—C5	−54.33 (18)
C4—C3A—C3—N2	112.1 (2)	C7—S8—C4—C9	−179.8 (2)
C7A—C3A—C3—O2	177.3 (2)	O3—S8—C7—C6	161.81 (16)
C7A—C3A—C3—N2	−3.5 (3)	C4—S8—C7—C6	55.41 (17)
C3—C3A—C4—S8	−156.84 (17)	O3—S8—C7—C7A	49.62 (19)
C3—C3A—C4—C5	−56.4 (3)	C4—S8—C7—C7A	−56.78 (16)
C3—C3A—C4—C9	79.6 (3)	C4—C9—C10—C11	−176.4 (4)
C7A—C3A—C4—S8	−42.1 (2)	N2—C12—C13—C14	−178.7 (3)
C7A—C3A—C4—C5	58.3 (3)	C17—C12—C13—C14	0.9 (4)
C7A—C3A—C4—C9	−165.7 (2)	N2—C12—C17—C16	178.1 (3)
C3—C3A—C7A—C1	0.7 (3)	C13—C12—C17—C16	−1.5 (4)
C3—C3A—C7A—C7	120.3 (2)	C12—C13—C14—C15	0.0 (5)
C4—C3A—C7A—C1	−118.6 (2)	C16—C15—C14—C13	−0.2 (6)
C4—C3A—C7A—C7	1.0 (3)	C14—C15—C16—C17	−0.4 (6)
S8—C4—C5—C6	41.1 (3)	C12—C17—C16—C15	1.3 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C12–C17 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95 (2)	2.51 (3)	3.326 (4)	144 (2)
C17—H17···O3ⁱⁱ	0.93	2.57	3.315 (3)	137
C7—H7···Cg1ⁱⁱⁱ	0.98	2.77	3.693 (3)	157

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO₃S
M_r	315.39
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	7.7712 (3), 10.8413 (3), 18.9762 (4)
V (Å³)	1598.74 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.807, 0.865
No. of measured, independent and observed [I > 2σ(I)] reflections	34450, 3279, 2686
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.108, 1.08
No. of reflections	3279
No. of parameters	210
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22
Absolute structure	Flack (1983), 1379 Friedel pairs
Absolute structure parameter	0.37 (9)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C12–C17 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95 (2)	2.51 (3)	3.326 (4)	144 (2)
C17—H17···O3ⁱⁱ	0.93	2.57	3.315 (3)	137
C7—H7···Cg1ⁱⁱⁱ	0.98	2.77	3.693 (3)	157

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

Acknowledgements

The authors are indebted to the Department of Chemistry, Atatürk University, Erzurum, Turkey, for use of the X-ray diffractometer purchased under grant No. 2003/219 of the University Research Fund. We thank The Scientific & Technological Research Council of Turkey (TUBITAK) for financial support of this work (PN: 107T831).

References

Al-Omran, F., Khalik, M. M. A., Al-Awadhi, H. & Elnagdi, M. H. (1996). Tetrahedron, 52, 11915–11928. CAS Google Scholar
Arslan, H. & Demircan, A. (2007). Acta Chim. Slov. 54, 341–353. CAS Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Koşar, B., Göktürk, E., Demircan, A. & Büyükgüngör, O. (2006). Acta Cryst. E62, o4192–o4193. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kotsuki, H., Kitagawa, S., Nishizawa, H. & Tokoroyama, T. (1978). J. Org. Chem., 43, 1471–1472. CrossRef CAS Google Scholar
Kuhn, H. J. & Gollnick, K. (1972). Tetrahedron Lett., pp. 1909–1912. Google Scholar
Lert, P. W. & Trindle, C. (1971). J. Am. Chem. Soc. 93, 6392–6395. CrossRef CAS Google Scholar
Rajappa, S. (1984). Compherensive Heterocyclic Chemistry, Vol. 4, edited by A. R. Katritzky & C. W. Rees, p. 841. New York: Pergamon Press. Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thiemann, T., Li, Y. Q., Mataka, S. & Tashiro, M. (1995). J. Chem. Res. (M), pp. 6364–6379. Google Scholar
Thiemann, T., Tanaka, Y. & Iniesta, J. (2009). Molecules, 14, 1013–1031. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 67| Part 5| May 2011| Pages o1085-o1086

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

(3aR,4S,7R,7aS)-2-Phenyl-4-propyl-3a,4,7,7a-tetra­hydro-1H-4,7-epi­thio­iso­indole-1,3-dione 8-oxide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3aR,4S,7R,7aS)-2-Phenyl-4-propyl-3a,4,7,7a-tetrahydro-1H-4,7-epithioisoindole-1,3-dione 8-oxide