(3aR,4S,7R,7aS)-2-Phenyl-4-propyl-3a,4,7,7a-tetra-hydro-1H-4,7-epithio-iso-indole-1,3-dione 8-oxide.

In the tetra-hydro-isoindole moiety of the title compound, C(17)H(17)NO(3)S, 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, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. A weak C-H⋯π inter-action 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 = 315.39

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.108

S = 1.08

3279 reflections

210 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1379 Friedel pairs

Flack parameter: 0.37 (9)

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 ▶).

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

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

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

C17H17NO3S	F(000) = 664
Mr = 315.39	Dx = 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

Rigaku R-AXIS RAPID-S diffractometer	3279 independent reflections
Radiation source: fine-focus sealed tube	2686 reflections with I > 2σ(I)
graphite	Rint = 0.088
ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (Blessing, 1995)	h = −9→9
Tmin = 0.807, Tmax = 0.865	k = −13→13
34450 measured reflections	l = −23→23

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(Fo2) + (0.0453P)2 + 0.1086P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.108	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.20 e Å−3
3279 reflections	Δρmin = −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	Flack parameter: 0.37 (9)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .