(3aR*,7aS*)-1-(p-Tolyl-sulfon-yl)perhydro-indol-2-one.

In the racemic title compound, C(15)H(19)NO(3)S, the dihedral angle between the planes of the benzene ring and the O=S=O group is 56.92 (7)° and the cyclo-hexane ring adopts a chair conformation.

Related literature

For related structures, see: Brion et al. (1992 ▶). For the medicinal background, see: De Ponti et al. (1991 ▶).

Experimental

Crystal data

C15H19NO3S

M = 293.37

Orthorhombic,

a = 15.6509 (12) Å

b = 5.9692 (5) Å

c = 15.7967 (13) Å

V = 1475.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 120 K

0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.946, T max = 0.961

7103 measured reflections

2702 independent reflections

2397 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.102

S = 1.01

2702 reflections

182 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1189 Friedel pairs

Flack parameter: 0.01 (10)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013139/hb5400sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013139/hb5400Isup2.hkl

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

C15H19NO3S	F(000) = 624
Mr = 293.37	Dx = 1.320 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2285 reflections
a = 15.6509 (12) Å	θ = 2.6–25.2°
b = 5.9692 (5) Å	µ = 0.23 mm−1
c = 15.7967 (13) Å	T = 120 K
V = 1475.8 (2) Å3	Block, colorless
Z = 4	0.25 × 0.20 × 0.18 mm

Bruker SMART CCD diffractometer	2702 independent reflections
Radiation source: fine-focus sealed tube	2397 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scan	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −19→19
Tmin = 0.946, Tmax = 0.961	k = −7→7
7103 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0603P)2 + 0.1589P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2702 reflections	Δρmax = 0.24 e Å−3
182 parameters	Δρmin = −0.17 e Å−3
1 restraint	Absolute structure: Flack (1983), 1189 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (10)

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 > 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
S1	−0.00414 (4)	0.18513 (9)	0.40616 (5)	0.03841 (17)
C1	−0.0558 (2)	0.0780 (5)	0.56190 (17)	0.0516 (7)
C2	−0.0387 (2)	−0.1072 (6)	0.62443 (18)	0.0629 (9)
H2A	−0.0509	−0.0577	0.6830	0.075*
H2B	−0.0737	−0.2410	0.6116	0.075*
C3	0.0549 (2)	−0.1554 (5)	0.61272 (16)	0.0489 (7)
H3A	0.0873	−0.0347	0.6426	0.059*
C4	0.0933 (2)	−0.3773 (5)	0.63948 (19)	0.0663 (9)
H4A	0.0644	−0.5014	0.6093	0.080*
H4B	0.0850	−0.3995	0.7010	0.080*
C5	0.1881 (2)	−0.3783 (6)	0.61869 (18)	0.0703 (10)
H5A	0.2118	−0.5287	0.6307	0.084*
H5B	0.2178	−0.2694	0.6557	0.084*
C6	0.2056 (2)	−0.3187 (6)	0.5266 (2)	0.0691 (10)
H6A	0.1856	−0.4431	0.4903	0.083*
H6B	0.2681	−0.3043	0.5185	0.083*
C7	0.16246 (19)	−0.1007 (5)	0.49752 (18)	0.0569 (8)
H7A	0.1872	0.0292	0.5277	0.068*
H7B	0.1708	−0.0789	0.4360	0.068*
C8	0.06903 (17)	−0.1222 (4)	0.51752 (16)	0.0395 (6)
H8A	0.0461	−0.2562	0.4871	0.047*
C9	−0.10350 (16)	0.0904 (4)	0.36999 (14)	0.0342 (5)
C10	−0.10958 (16)	−0.1217 (4)	0.33444 (15)	0.0376 (5)
H10A	−0.0614	−0.2183	0.3332	0.045*
C11	−0.18653 (18)	−0.1900 (4)	0.30096 (15)	0.0405 (6)
H11A	−0.1912	−0.3357	0.2773	0.049*
C12	−0.25761 (16)	−0.0497 (4)	0.30111 (15)	0.0391 (6)
C13	−0.25008 (16)	0.1610 (4)	0.33775 (17)	0.0403 (6)
H13A	−0.2981	0.2585	0.3385	0.048*
C14	−0.17402 (17)	0.2307 (4)	0.37301 (15)	0.0374 (6)
H14A	−0.1700	0.3737	0.3991	0.045*
C15	−0.3410 (2)	−0.1241 (5)	0.26208 (19)	0.0546 (7)
H15A	−0.3581	−0.2681	0.2866	0.066*
H15B	−0.3337	−0.1408	0.2008	0.066*
H15C	−0.3852	−0.0119	0.2735	0.066*
N1	0.01047 (13)	0.0708 (3)	0.50183 (13)	0.0401 (5)
O1	−0.11421 (15)	0.2106 (4)	0.55905 (13)	0.0689 (6)
O2	−0.00807 (12)	0.4227 (3)	0.41542 (15)	0.0541 (6)
O3	0.06024 (11)	0.0901 (3)	0.35308 (11)	0.0479 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0388 (4)	0.0307 (3)	0.0457 (3)	−0.0040 (2)	−0.0067 (3)	0.0048 (3)
C1	0.0526 (19)	0.0666 (18)	0.0355 (12)	0.0096 (15)	−0.0052 (12)	−0.0115 (13)
C2	0.064 (2)	0.089 (2)	0.0359 (13)	0.0132 (19)	0.0076 (14)	0.0059 (14)
C3	0.060 (2)	0.0554 (16)	0.0316 (11)	0.0074 (14)	−0.0060 (12)	−0.0037 (11)
C4	0.096 (3)	0.0637 (19)	0.0396 (15)	0.0170 (18)	−0.0036 (16)	0.0128 (13)
C5	0.089 (3)	0.079 (2)	0.0424 (15)	0.038 (2)	−0.0088 (16)	0.0009 (14)
C6	0.073 (2)	0.088 (2)	0.0465 (16)	0.0378 (19)	−0.0027 (16)	0.0060 (15)
C7	0.046 (2)	0.0692 (19)	0.0554 (17)	0.0109 (14)	−0.0035 (14)	0.0126 (15)
C8	0.0482 (16)	0.0333 (12)	0.0370 (12)	0.0049 (11)	−0.0065 (11)	−0.0023 (10)
C9	0.0394 (15)	0.0287 (11)	0.0346 (11)	−0.0015 (9)	−0.0004 (11)	0.0042 (9)
C10	0.0437 (16)	0.0320 (12)	0.0370 (11)	0.0077 (10)	0.0004 (12)	0.0007 (10)
C11	0.0502 (17)	0.0343 (13)	0.0370 (12)	−0.0016 (11)	−0.0008 (11)	−0.0045 (9)
C12	0.0418 (16)	0.0415 (13)	0.0340 (11)	−0.0054 (11)	−0.0030 (10)	0.0033 (10)
C13	0.0375 (16)	0.0408 (13)	0.0425 (12)	0.0045 (10)	−0.0036 (11)	0.0005 (10)
C14	0.0412 (16)	0.0298 (11)	0.0414 (11)	0.0022 (10)	−0.0015 (11)	−0.0017 (10)
C15	0.047 (2)	0.0621 (18)	0.0543 (16)	−0.0116 (14)	−0.0083 (13)	−0.0042 (14)
N1	0.0433 (14)	0.0376 (12)	0.0394 (11)	0.0038 (9)	−0.0038 (9)	−0.0045 (9)
O1	0.0639 (15)	0.0967 (17)	0.0462 (11)	0.0313 (13)	−0.0031 (10)	−0.0131 (11)
O2	0.0524 (13)	0.0302 (9)	0.0797 (15)	−0.0061 (8)	−0.0220 (11)	0.0006 (11)
O3	0.0392 (11)	0.0581 (11)	0.0463 (10)	−0.0009 (8)	0.0028 (8)	0.0126 (8)

S1—O2	1.4267 (17)	C6—H6B	0.9900
S1—O3	1.4281 (19)	C7—C8	1.502 (4)
S1—N1	1.674 (2)	C7—H7A	0.9900
S1—C9	1.750 (2)	C7—H7B	0.9900
C1—O1	1.210 (3)	C8—N1	1.493 (3)
C1—N1	1.406 (4)	C8—H8A	1.0000
C1—C2	1.507 (4)	C9—C14	1.386 (3)
C2—C3	1.505 (5)	C9—C10	1.388 (3)
C2—H2A	0.9900	C10—C11	1.377 (4)
C2—H2B	0.9900	C10—H10A	0.9500
C3—C4	1.514 (4)	C11—C12	1.392 (4)
C3—C8	1.533 (3)	C11—H11A	0.9500
C3—H3A	1.0000	C12—C13	1.389 (3)
C4—C5	1.520 (5)	C12—C15	1.510 (4)
C4—H4A	0.9900	C13—C14	1.379 (3)
C4—H4B	0.9900	C13—H13A	0.9500
C5—C6	1.522 (4)	C14—H14A	0.9500
C5—H5A	0.9900	C15—H15A	0.9800
C5—H5B	0.9900	C15—H15B	0.9800
C6—C7	1.537 (4)	C15—H15C	0.9800
C6—H6A	0.9900
O2—S1—O3	119.03 (12)	C8—C7—C6	107.0 (3)
O2—S1—N1	108.56 (11)	C8—C7—H7A	110.3
O3—S1—N1	105.77 (10)	C6—C7—H7A	110.3
O2—S1—C9	108.42 (10)	C8—C7—H7B	110.3
O3—S1—C9	107.88 (12)	C6—C7—H7B	110.3
N1—S1—C9	106.52 (11)	H7A—C7—H7B	108.6
O1—C1—N1	123.5 (3)	N1—C8—C7	119.8 (2)
O1—C1—C2	129.7 (3)	N1—C8—C3	100.0 (2)
N1—C1—C2	106.8 (2)	C7—C8—C3	111.0 (2)
C3—C2—C1	103.5 (2)	N1—C8—H8A	108.5
C3—C2—H2A	111.1	C7—C8—H8A	108.5
C1—C2—H2A	111.1	C3—C8—H8A	108.5
C3—C2—H2B	111.1	C14—C9—C10	120.7 (2)
C1—C2—H2B	111.1	C14—C9—S1	120.07 (17)
H2A—C2—H2B	109.0	C10—C9—S1	119.17 (18)
C2—C3—C4	121.3 (3)	C11—C10—C9	119.0 (2)
C2—C3—C8	103.7 (2)	C11—C10—H10A	120.5
C4—C3—C8	109.3 (2)	C9—C10—H10A	120.5
C2—C3—H3A	107.3	C10—C11—C12	121.3 (2)
C4—C3—H3A	107.3	C10—C11—H11A	119.3
C8—C3—H3A	107.3	C12—C11—H11A	119.3
C3—C4—C5	109.3 (3)	C13—C12—C11	118.5 (2)
C3—C4—H4A	109.8	C13—C12—C15	120.7 (2)
C5—C4—H4A	109.8	C11—C12—C15	120.8 (2)
C3—C4—H4B	109.8	C14—C13—C12	121.0 (2)
C5—C4—H4B	109.8	C14—C13—H13A	119.5
H4A—C4—H4B	108.3	C12—C13—H13A	119.5
C4—C5—C6	112.4 (3)	C13—C14—C9	119.4 (2)
C4—C5—H5A	109.1	C13—C14—H14A	120.3
C6—C5—H5A	109.1	C9—C14—H14A	120.3
C4—C5—H5B	109.1	C12—C15—H15A	109.5
C6—C5—H5B	109.1	C12—C15—H15B	109.5
H5A—C5—H5B	107.9	H15A—C15—H15B	109.5
C5—C6—C7	113.8 (2)	C12—C15—H15C	109.5
C5—C6—H6A	108.8	H15A—C15—H15C	109.5
C7—C6—H6A	108.8	H15B—C15—H15C	109.5
C5—C6—H6B	108.8	C1—N1—C8	111.4 (2)
C7—C6—H6B	108.8	C1—N1—S1	119.73 (18)
H6A—C6—H6B	107.7	C8—N1—S1	123.25 (16)