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

Wu, M.; Hu, Y.-M.

doi:10.1107/S1600536813011045

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o926

doi:10.1107/S1600536813011045

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

Min Wu ^a and Yi-Min Hu ^a ^*

^aSchool of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, People's Republic of China
^*Correspondence e-mail: yiminhu@yahoo.cn

(Received 9 March 2013; accepted 23 April 2013; online 18 May 2013)

The title compound, C₁₉H₁₉NO₃S, was produced by the self-reaction of N-cinnamyl-N-tosylacrylamide in the presence of palladium(II) acetate via an intramolecular C—C coupling reaction and C—H activation. There are two chiral C atoms in the molecule, but the crystal is a racemic system due to a lack of chiral separation. The five-membered ring is twisted about the methylene–methane bond, and the cyclohexa-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 molecule. In the crystal, the presence of C—H⋯π interactions 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_r = 341.41
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.140
S = 1.00
3724 reflections
218 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) -x+1, -y, -z+2.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813011045/bv2220sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813011045/bv2220Isup3.cml

checkCIF report

Comment top

Palladium-catalyzed intermolecular and intramolecular reactions have become an important tool of modern organic synthesis chemistry(Zhao et al., 2012). They have made a wide variety of active pharmaceutical ingredients and complex organic molecules economically accessible(Hu et al., 2009; Hu et al., 2010). The benzo[f]isoindol-1-one derivatives, which have physiological activity, are effective intermediates in the preparation of many complex natural products(Pitchumani et al., 2010). We have reported some novel palladium-catalyzed coupling reactions of aryl halides with the olefins and dienes(Meng et al., 2011; Hu et al., 2011). The self-reaction of N-cinnamyl-N-tosylacrylamide, in the presence of palladium(II) acetate and triphenylphosphine, in DMF at 393 K for 16 h, gave the unexpected title product.

The crystal structure data of molecule (I), C₁₉H₁₉NO₃S, reveals that all the bond lengths and angles have normal values. An asymmetric unit is composed of one title compound molecule. The title compound molecule contains two phenyl ring, one five-member carbon ring, and one six-member carbon ring. All the rings are not coplanar (figure 1). In the molecule (I) there are two chiral carbon atoms, C8 and C9, but the crystal is a racemic system due to lacking of the chiral separation. The five-membered ring is twisted about the methylene–methane bond, and the cyclohexa-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 molecule. In the crystal, the presence of C—H···π interactions leads to inversion dimers. The molecules with R, S(C8, C9) conformation form a 1-D chain through weak H9···O₁ⁱ(i: 1 + x, y,z) interactions, so do molecules with S, R(C8ⁱⁱⁱ, C9ⁱⁱⁱ) conformation (H9ⁱⁱⁱ···O₁^iv (iii: -x, 1 - y,1 - z; iv: 1 - x,1 - y,1 - z). Two chains are parallel with each other along the a axis(Fig. 2).

Related literature top

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 top

An oven-dried Schlenk flask was evacuated, filled with nitrogen, and then charged with N-cinnamyl-N-tosylacrylamide (3.41 g, 10 mmol), tributylamine (3 ml), PPh₃ (52.5 mg, 0.2 mmol), Pd(OAc)₂ (24 mg, 0.1 mol), and DMF (10 ml) to give a yellow solution. The reaction mixture was heated at 393 K with stirring. The reaction mixture was cooled to room temperature after 16 h and the resultant yellow-orange mixture was diluted with Et₂O (10 ml). The mixture was washed with H₂O (15 ml) and the aqueous layer was extracted with Et₂O (20 ml). The combined organic layers were dried (MgSO₄), filtered, and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (petroleum ester:EtOAc = 7:1) and recrystalized from EtOAc, yield 3.11 g (91%). Colorless crystals suitable for X-ray diffraction were obtained by recrystallization from a solution of the title compound from ethyl acetate over a period of one week.

Computing details top

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

Figures top

	Fig. 1. A view of the title compound showing the atom-numbering scheme and displacement ellipsoids drawn at 30% probability level.
	Fig. 2. A view of the forming a 1-D chain along the a axis. (i: 1 + x, y, z; ii: -1 + x,y,z; iii:-x,1 - y,1 - z; iv: 1 - x,1 - y,1 - z; v: 2 - x,1 - y,1 - z)
	Fig. 3. A view of the cell packing.
	Fig. 4. The formation of the title compound.

2-Tosyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindol-1-one top

Crystal data top

C₁₉H₁₉NO₃S	Z = 2
M_r = 341.41	F(000) = 360
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0538P)² + 0.0132P] where P = (F_o² + 2F_c²)/3
3724 reflections	(Δ/σ)_max = 0.002
218 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₉H₁₉NO₃S	γ = 81.224 (2)°
M_r = 341.41	V = 830.75 (16) Å³
Triclinic, P1	Z = 2
a = 6.4389 (8) Å	Mo Kα radiation
b = 8.4336 (11) Å	µ = 0.21 mm⁻¹
c = 15.4958 (12) Å	T = 291 K
α = 89.312 (2)°	0.28 × 0.24 × 0.22 mm
β = 87.395 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	3724 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1902 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.955	R_int = 0.041
7242 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	1 restraint
wR(F²) = 0.140	H-atom parameters constrained
S = 1.00	Δρ_max = 0.19 e Å⁻³
3724 reflections	Δρ_min = −0.27 e Å⁻³
218 parameters

Special details top

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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉NO₃S
M_r	341.41
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	6.4389 (8), 8.4336 (11), 15.4958 (12)
α, β, γ (°)	89.312 (2), 87.395 (3), 81.224 (2)
V (Å³)	830.75 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.28 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.943, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	7242, 3724, 1902
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.140, 1.00
No. of reflections	3724
No. of parameters	218
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.27

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+2.

Acknowledgements

We thank the National Science Foundation of China (project Nos. 21272005 and 21072003) for financial support for this work.

References

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