2-Tosyl-2,3,3a,4,9,9a-hexa-hydro-1H-benzo[f]isoindol-1-one.

The title compound, C19H19NO3S, was produced by the self-reaction of N-cinnamyl-N-tosyl-acryl-amide in the presence of palladium(II) acetate via an intra-molecular C-C coupling reaction and C-H activation. There are two chiral C atoms in the mol-ecule, but the crystal is a racemic system due to a lack of chiral separation. The five-membered ring is twisted about the methyl-ene-methane bond, and the cyclo-hexa-1,4-diene ring has a boat conformation. The dihedral angle between the benzene rings is 88.27 (14)°, indicating an almost orthogonal relationship and an approximate L-shape for the mol-ecule. In the crystal, the presence of C-H⋯π inter-actions leads to inversion dimers.

Related literature

For palladium-catalysed inter­molecular and intra­molecular reactions, see: Zhao et al. (2012 ▶) and for palladium-catalysed coupling reactions, see: Meng et al. (2011 ▶); Hu et al. (2011 ▶). They have made a wide variety active pharmaceutical ingredients and complex organic mol­ecules economically accessible, see: Hu et al. (2009 ▶, 2010 ▶). For the physiological activity of benzo[f]isoindol-1-one derivatives, see: Pitchumani & Vijaikumar (2010 ▶).

Experimental

Crystal data

C19H19NO3S

M = 341.41

Triclinic,

a = 6.4389 (8) Å

b = 8.4336 (11) Å

c = 15.4958 (12) Å

α = 89.312 (2)°

β = 87.395 (3)°

γ = 81.224 (2)°

V = 830.75 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 291 K

0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.943, T max = 0.955

7242 measured reflections

3724 independent reflections

1902 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.140

S = 1.00

3724 reflections

218 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.27 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011045/bv2220sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011045/bv2220Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011045/bv2220Isup3.cml

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

C19H19NO3S	Z = 2
Mr = 341.41	F(000) = 360
Triclinic, P1	Dx = 1.365 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4389 (8) Å	Cell parameters from 3121 reflections
b = 8.4336 (11) Å	θ = 2.1–23.6°
c = 15.4958 (12) Å	µ = 0.21 mm−1
α = 89.312 (2)°	T = 291 K
β = 87.395 (3)°	Block, colorless
γ = 81.224 (2)°	0.28 × 0.24 × 0.22 mm
V = 830.75 (16) Å3

Bruker SMART APEX CCD diffractometer	3724 independent reflections
Radiation source: sealed tube	1902 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
phi and ω scans	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.943, Tmax = 0.955	k = −10→10
7242 measured reflections	l = −20→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0538P)2 + 0.0132P] where P = (Fo2 + 2Fc2)/3
3724 reflections	(Δ/σ)max = 0.002
218 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.27 e Å−3

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
C1	0.3560 (5)	0.2477 (3)	1.14379 (19)	0.0529 (8)
H1	0.2229	0.2911	1.1658	0.063*
C2	0.5104 (6)	0.1853 (4)	1.1995 (2)	0.0632 (9)
H2	0.4793	0.1846	1.2587	0.076*
C3	0.7085 (6)	0.1248 (4)	1.1681 (2)	0.0632 (9)
H3	0.8121	0.0837	1.2058	0.076*
C4	0.7530 (5)	0.1253 (3)	1.0804 (2)	0.0516 (8)
H4	0.8885	0.0863	1.0593	0.062*
C5	0.6001 (4)	0.1827 (3)	1.02266 (18)	0.0402 (7)
C6	0.3994 (4)	0.2456 (3)	1.05538 (18)	0.0420 (7)
C7	0.2351 (4)	0.3035 (4)	0.99167 (19)	0.0509 (8)
H7A	0.1217	0.3744	1.0211	0.061*
H7B	0.1771	0.2121	0.9711	0.061*
C8	0.3179 (4)	0.3927 (3)	0.91382 (17)	0.0402 (7)
H8	0.2959	0.5078	0.9264	0.048*
C9	0.5518 (4)	0.3398 (3)	0.88727 (16)	0.0383 (7)
H9	0.6331	0.4209	0.9067	0.046*
C10	0.6378 (4)	0.1798 (3)	0.92661 (17)	0.0421 (7)
H10A	0.5702	0.0963	0.9024	0.050*
H10B	0.7876	0.1552	0.9127	0.050*
C11	0.5606 (4)	0.3383 (4)	0.78857 (18)	0.0474 (8)
H11A	0.6051	0.4355	0.7652	0.057*
H11B	0.6567	0.2464	0.7666	0.057*
C12	0.1997 (5)	0.3657 (4)	0.83510 (19)	0.0478 (7)
C13	0.1097 (4)	0.4760 (3)	0.64007 (17)	0.0424 (7)
C14	−0.0883 (4)	0.4722 (4)	0.61141 (18)	0.0510 (8)
H14	−0.1412	0.3758	0.6087	0.061*
C15	−0.2072 (5)	0.6144 (5)	0.58664 (19)	0.0614 (9)
H15	−0.3399	0.6120	0.5658	0.074*
C16	−0.1359 (6)	0.7594 (4)	0.59177 (19)	0.0621 (9)
C17	0.0634 (6)	0.7592 (4)	0.6211 (2)	0.0703 (10)
H17	0.1151	0.8558	0.6252	0.084*
C18	0.1867 (5)	0.6194 (4)	0.6445 (2)	0.0631 (9)
H18	0.3215	0.6214	0.6632	0.076*
C19	−0.2678 (6)	0.9147 (5)	0.5653 (2)	0.0981 (14)
H19A	−0.2730	0.9919	0.6106	0.147*
H19B	−0.4078	0.8957	0.5549	0.147*
H19C	−0.2064	0.9551	0.5135	0.147*
N1	0.3425 (3)	0.3281 (3)	0.76626 (14)	0.0429 (6)
O1	0.0116 (3)	0.3754 (3)	0.83041 (14)	0.0784 (8)
O2	0.4664 (3)	0.2878 (3)	0.61566 (13)	0.0654 (6)
O3	0.1562 (4)	0.1696 (2)	0.66729 (15)	0.0769 (7)
S1	0.27381 (13)	0.29881 (9)	0.66632 (5)	0.0514 (3)

	U11	U22	U33	U12	U13	U23
C1	0.062 (2)	0.0443 (18)	0.051 (2)	−0.0084 (16)	0.0091 (17)	−0.0015 (15)
C2	0.088 (3)	0.062 (2)	0.0405 (19)	−0.015 (2)	−0.0038 (19)	−0.0014 (16)
C3	0.073 (3)	0.062 (2)	0.056 (2)	−0.012 (2)	−0.0174 (19)	0.0071 (17)
C4	0.0528 (19)	0.0468 (18)	0.056 (2)	−0.0073 (15)	−0.0084 (16)	0.0053 (15)
C5	0.0443 (17)	0.0313 (15)	0.0456 (18)	−0.0079 (13)	−0.0024 (14)	0.0049 (12)
C6	0.0468 (18)	0.0358 (16)	0.0434 (18)	−0.0082 (14)	0.0033 (14)	0.0000 (13)
C7	0.0381 (17)	0.0528 (19)	0.060 (2)	−0.0048 (14)	0.0082 (15)	0.0021 (15)
C8	0.0320 (16)	0.0358 (16)	0.0514 (18)	−0.0013 (12)	0.0003 (13)	0.0006 (13)
C9	0.0311 (15)	0.0395 (16)	0.0451 (17)	−0.0082 (12)	−0.0022 (12)	0.0026 (12)
C10	0.0351 (16)	0.0374 (16)	0.0523 (19)	−0.0018 (13)	0.0004 (13)	−0.0018 (13)
C11	0.0303 (16)	0.058 (2)	0.0524 (19)	−0.0017 (14)	−0.0056 (13)	0.0079 (14)
C12	0.0337 (17)	0.055 (2)	0.054 (2)	−0.0039 (14)	−0.0043 (15)	0.0103 (15)
C13	0.0415 (17)	0.0445 (17)	0.0409 (17)	−0.0038 (14)	−0.0073 (13)	0.0063 (13)
C14	0.0422 (18)	0.065 (2)	0.0459 (19)	−0.0080 (16)	−0.0033 (15)	0.0028 (15)
C15	0.0412 (19)	0.089 (3)	0.049 (2)	0.0066 (19)	−0.0047 (15)	0.0037 (19)
C16	0.068 (2)	0.069 (2)	0.0385 (19)	0.0218 (19)	0.0013 (17)	0.0017 (16)
C17	0.089 (3)	0.050 (2)	0.070 (2)	−0.001 (2)	−0.020 (2)	0.0058 (18)
C18	0.057 (2)	0.055 (2)	0.078 (3)	−0.0072 (18)	−0.0216 (18)	0.0065 (18)
C19	0.115 (3)	0.087 (3)	0.073 (3)	0.046 (3)	−0.009 (2)	0.013 (2)
N1	0.0325 (13)	0.0520 (15)	0.0437 (15)	−0.0036 (11)	−0.0070 (11)	0.0052 (11)
O1	0.0266 (12)	0.135 (2)	0.0729 (17)	−0.0107 (13)	−0.0060 (11)	0.0115 (15)
O2	0.0576 (12)	0.0761 (16)	0.0547 (14)	0.0166 (12)	−0.0041 (9)	−0.0101 (11)
O3	0.0937 (18)	0.0507 (14)	0.0942 (18)	−0.0258 (13)	−0.0428 (14)	0.0088 (12)
S1	0.0530 (5)	0.0458 (5)	0.0553 (5)	−0.0035 (4)	−0.0151 (4)	−0.0002 (4)

C1—C2	1.385 (4)	C11—N1	1.477 (3)
C1—C6	1.385 (4)	C11—H11A	0.9700
C1—H1	0.9300	C11—H11B	0.9700
C2—C3	1.369 (4)	C12—O1	1.207 (3)
C2—H2	0.9300	C12—N1	1.383 (3)
C3—C4	1.378 (4)	C13—C14	1.374 (4)
C3—H3	0.9300	C13—C18	1.379 (4)
C4—C5	1.388 (4)	C13—S1	1.749 (3)
C4—H4	0.9300	C14—C15	1.381 (4)
C5—C6	1.396 (4)	C14—H14	0.9300
C5—C10	1.497 (4)	C15—C16	1.375 (5)
C6—C7	1.503 (4)	C15—H15	0.9300
C7—C8	1.532 (4)	C16—C17	1.381 (5)
C7—H7A	0.9700	C16—C19	1.511 (4)
C7—H7B	0.9700	C17—C18	1.372 (4)
C8—C12	1.504 (4)	C17—H17	0.9300
C8—C9	1.542 (3)	C18—H18	0.9300
C8—H8	0.9800	C19—H19A	0.9600
C9—C10	1.511 (3)	C19—H19B	0.9600
C9—C11	1.528 (4)	C19—H19C	0.9600
C9—H9	0.9800	N1—S1	1.661 (2)
C10—H10A	0.9700	O2—S1	1.428 (2)
C10—H10B	0.9700	O3—S1	1.419 (2)
C2—C1—C6	120.1 (3)	N1—C11—C9	104.1 (2)
C2—C1—H1	119.9	N1—C11—H11A	110.9
C6—C1—H1	119.9	C9—C11—H11A	110.9
C3—C2—C1	120.5 (3)	N1—C11—H11B	110.9
C3—C2—H2	119.7	C9—C11—H11B	110.9
C1—C2—H2	119.7	H11A—C11—H11B	108.9
C2—C3—C4	119.4 (3)	O1—C12—N1	124.1 (3)
C2—C3—H3	120.3	O1—C12—C8	127.0 (3)
C4—C3—H3	120.3	N1—C12—C8	108.8 (2)
C3—C4—C5	121.4 (3)	C14—C13—C18	120.4 (3)
C3—C4—H4	119.3	C14—C13—S1	120.8 (2)
C5—C4—H4	119.3	C18—C13—S1	118.7 (2)
C4—C5—C6	118.6 (3)	C13—C14—C15	118.6 (3)
C4—C5—C10	123.6 (3)	C13—C14—H14	120.7
C6—C5—C10	117.8 (2)	C15—C14—H14	120.7
C1—C6—C5	119.8 (3)	C16—C15—C14	122.2 (3)
C1—C6—C7	122.5 (3)	C16—C15—H15	118.9
C5—C6—C7	117.7 (2)	C14—C15—H15	118.9
C6—C7—C8	113.8 (2)	C15—C16—C17	117.7 (3)
C6—C7—H7A	108.8	C15—C16—C19	121.9 (4)
C8—C7—H7A	108.8	C17—C16—C19	120.4 (4)
C6—C7—H7B	108.8	C18—C17—C16	121.4 (3)
C8—C7—H7B	108.8	C18—C17—H17	119.3
H7A—C7—H7B	107.7	C16—C17—H17	119.3
C12—C8—C7	110.1 (2)	C17—C18—C13	119.6 (3)
C12—C8—C9	105.1 (2)	C17—C18—H18	120.2
C7—C8—C9	115.3 (2)	C13—C18—H18	120.2
C12—C8—H8	108.7	C16—C19—H19A	109.5
C7—C8—H8	108.7	C16—C19—H19B	109.5
C9—C8—H8	108.7	H19A—C19—H19B	109.5
C10—C9—C11	113.2 (2)	C16—C19—H19C	109.5
C10—C9—C8	112.0 (2)	H19A—C19—H19C	109.5
C11—C9—C8	105.2 (2)	H19B—C19—H19C	109.5
C10—C9—H9	108.8	C12—N1—C11	112.5 (2)
C11—C9—H9	108.8	C12—N1—S1	123.75 (19)
C8—C9—H9	108.8	C11—N1—S1	123.24 (19)
C5—C10—C9	110.7 (2)	O3—S1—O2	119.80 (15)
C5—C10—H10A	109.5	O3—S1—N1	108.71 (13)
C9—C10—H10A	109.5	O2—S1—N1	104.22 (12)
C5—C10—H10B	109.5	O3—S1—C13	109.13 (14)
C9—C10—H10B	109.5	O2—S1—C13	109.42 (13)
H10A—C10—H10B	108.1	N1—S1—C13	104.41 (12)
C6—C1—C2—C3	1.6 (5)	C18—C13—C14—C15	0.5 (4)
C1—C2—C3—C4	−0.4 (5)	S1—C13—C14—C15	−176.2 (2)
C2—C3—C4—C5	−1.4 (5)	C13—C14—C15—C16	−1.6 (5)
C3—C4—C5—C6	2.1 (4)	C14—C15—C16—C17	1.4 (5)
C3—C4—C5—C10	−177.4 (3)	C14—C15—C16—C19	−179.4 (3)
C2—C1—C6—C5	−1.0 (4)	C15—C16—C17—C18	0.0 (5)
C2—C1—C6—C7	176.7 (3)	C19—C16—C17—C18	−179.2 (3)
C4—C5—C6—C1	−0.8 (4)	C16—C17—C18—C13	−1.1 (5)
C10—C5—C6—C1	178.6 (2)	C14—C13—C18—C17	0.8 (5)
C4—C5—C6—C7	−178.6 (2)	S1—C13—C18—C17	177.6 (2)
C10—C5—C6—C7	0.9 (4)	O1—C12—N1—C11	175.1 (3)
C1—C6—C7—C8	142.4 (3)	C8—C12—N1—C11	−4.5 (3)
C5—C6—C7—C8	−39.9 (3)	O1—C12—N1—S1	2.8 (4)
C6—C7—C8—C12	148.4 (2)	C8—C12—N1—S1	−176.76 (18)
C6—C7—C8—C9	29.6 (3)	C9—C11—N1—C12	16.0 (3)
C12—C8—C9—C10	−105.2 (3)	C9—C11—N1—S1	−171.72 (18)
C7—C8—C9—C10	16.3 (3)	C12—N1—S1—O3	−59.7 (3)
C12—C8—C9—C11	18.1 (3)	C11—N1—S1—O3	128.9 (2)
C7—C8—C9—C11	139.6 (2)	C12—N1—S1—O2	171.5 (2)
C4—C5—C10—C9	−133.4 (3)	C11—N1—S1—O2	0.1 (3)
C6—C5—C10—C9	47.2 (3)	C12—N1—S1—C13	56.7 (2)
C11—C9—C10—C5	−172.8 (2)	C11—N1—S1—C13	−114.7 (2)
C8—C9—C10—C5	−54.2 (3)	C14—C13—S1—O3	−10.0 (3)
C10—C9—C11—N1	102.2 (2)	C18—C13—S1—O3	173.2 (2)
C8—C9—C11—N1	−20.3 (3)	C14—C13—S1—O2	122.8 (2)
C7—C8—C12—O1	46.7 (4)	C18—C13—S1—O2	−53.9 (3)
C9—C8—C12—O1	171.6 (3)	C14—C13—S1—N1	−126.1 (2)
C7—C8—C12—N1	−133.7 (2)	C18—C13—S1—N1	57.1 (3)
C9—C8—C12—N1	−8.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···Cg1i	0.97	2.63	3.555 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cg1i	0.97	2.63	3.555 (3)	159

Symmetry code: (i) .