(Z)-3-(1-Chloro­prop-1-en­yl)-2-methyl-1-phenyl­sulfonyl-1H-indole

Umadevi, M.; Saravanan, V.; Yamuna, R.; Mohanakrishnan, A.K.; Chakkaravarthi, G.

doi:10.1107/S1600536813030730

organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1781

doi:10.1107/S1600536813030730

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(Z)-3-(1-Chloroprop-1-enyl)-2-methyl-1-phenylsulfonyl-1H-indole

M. Umadevi,^a V. Saravanan,^b R. Yamuna,^c ^* A. K. Mohanakrishnan ^b and G. Chakkaravarthi ^d ^*

^aResearch Scholar (Chemistry), Bharathiyar University, Coimbatore 641 046, Tamilnadu, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Sciences, Chemistry and Materials Research Lab, Amrita Vishwa Vidyapeetham University, Ettimadai, Coimbatore 641 112, India, and ^dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: ryamuna1@gmail.com, chakkaravarthi_2005@yahoo.com

(Received 6 November 2013; accepted 8 November 2013; online 16 November 2013)

In the title compound, C₁₈H₁₆ClNO₂S, the indole ring system forms a dihedral angle of 75.07 (8)° with the phenyl ring. The molecular structure is stabilized by a weak intramolecular C—H⋯O hydrogen bond. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming a chain along [10-1]. C—H⋯π interactions are also observed, leading to a three-dimensional network.

CCDC reference: 971044

Related literature

For the biological activity of indole derivatives, see: Okabe & Adachi (1998 ); Schollmeyer et al. (1995 ). For related structures, see: Chakkaravarthi et al. (2007 , 2008 ).

Experimental

Crystal data

C₁₈H₁₆ClNO₂S
M_r = 345.83
Monoclinic, P 2₁ /n
a = 12.5204 (10) Å
b = 10.4962 (7) Å
c = 12.983 (1) Å
β = 98.892 (2)°
V = 1685.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.906, T_max = 0.938
20036 measured reflections
4705 independent reflections
3357 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.118
S = 1.03
4705 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C7/C12–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.93	2.39	2.973 (2)	120
C10—H10⋯O2ⁱ	0.93	2.49	3.364 (2)	157
C5—H5⋯Cg1ⁱⁱ	0.93	2.82	3.477 (2)	128
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{3\over 2}}, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 971044

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813030730/is5320sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813030730/is5320Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813030730/is5320Isup3.cml

checkCIF report

Comment top

The indole derivatives are known to exhibit anti-bacterial and anti-tumour activities (Okabe & Adachi, 1998; Schollmeyer et al., 1995). We herein report the crystal structure of the title compound (I), (Fig. 1). The geometric parameters of (I) are comparable with the reported similar structures (Chakkaravarthi et al., 2007, 2008). The phenyl ring forms a dihedral angle of 75.07 (8)° with the indole ring system. The five-membered (N1/C7/C12–C14) and six-membered (C7–C12) rings in the indole ring system are planar, with a dihedral angle of 0.38 (9)° between these rings. The bond angles around N1 (351.5°) indicate the sp² hybridization of N1 atom. The molecular structure is stabilized by a weak intramolecular C—H···O (Table 1) hydrogen bond. The crystal structure exhibits weak intermolecular C—H···O (Fig. 2) and C—H···π (Table 1) interactions.

Related literature top

For the biological activity of indole derivatives, see: Okabe & Adachi (1998); Schollmeyer et al. (1995). For related structures, see: Chakkaravarthi et al. (2007, 2008).

Experimental top

To a solution of 2-methyl-1-(phenylsulfonyl)-1H-indole (1 g, 3.69 mmol) in dry dichloromethane (20 ml), AlCl₃ (1.47 g, 11.07 mmol) and propionic anhydride (0.71 ml, 5.53 mmol) were added at 0 °C and stirred for 3 h. Then, the reaction mixture was washed with saturated NaHCO₃ (2 × 10 ml) solution, followed by water (3 × 10 ml) and dried (Na₂SO₄). Removal of the solvent followed a column chromatographic purification (Silica gel; hexane-ethyl acetate, 95:5) afforded the title compound, suitable for X-Ray diffraction quality crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A packing diagram of the title compound, view down the b axis. Intermolecular hydrogen bonds are shown as dashed lines. H atoms not involving hydrogen bonding have been omitted.

(Z)-3-(1-chloroprop-1-enyl)-2-methyl-1-phenylsulfonyl-1H-indole top

Crystal data top

C₁₈H₁₆ClNO₂S	F(000) = 720
M_r = 345.83	D_x = 1.363 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6694 reflections
a = 12.5204 (10) Å	θ = 2.1–27.9°
b = 10.4962 (7) Å	µ = 0.36 mm⁻¹
c = 12.983 (1) Å	T = 295 K
β = 98.892 (2)°	Block, colourless
V = 1685.7 (2) Å³	0.28 × 0.24 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4705 independent reflections
Radiation source: fine-focus sealed tube	3357 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω and ϕ scan	θ_max = 29.6°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
T_min = 0.906, T_max = 0.938	k = −14→8
20036 measured reflections	l = −17→17

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.048P)² + 0.5443P] where P = (F_o² + 2F_c²)/3
4705 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₈H₁₆ClNO₂S	V = 1685.7 (2) Å³
M_r = 345.83	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.5204 (10) Å	µ = 0.36 mm⁻¹
b = 10.4962 (7) Å	T = 295 K
c = 12.983 (1) Å	0.28 × 0.24 × 0.18 mm
β = 98.892 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	4705 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3357 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.938	R_int = 0.032
20036 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.03	Δρ_max = 0.26 e Å⁻³
4705 reflections	Δρ_min = −0.38 e Å⁻³
210 parameters

Special details top

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	0.59725 (13)	0.25271 (15)	0.25702 (12)	0.0409 (4)
C2	0.61126 (16)	0.36677 (19)	0.20771 (15)	0.0538 (4)
H2	0.6791	0.4046	0.2140	0.065*
C3	0.52304 (19)	0.4234 (2)	0.14909 (17)	0.0662 (6)
H3	0.5310	0.5006	0.1159	0.079*
C4	0.42317 (19)	0.3664 (2)	0.13940 (17)	0.0677 (6)
H4	0.3641	0.4048	0.0990	0.081*
C5	0.41016 (17)	0.2544 (2)	0.18844 (18)	0.0658 (6)
H5	0.3421	0.2170	0.1817	0.079*
C6	0.49712 (15)	0.19547 (18)	0.24823 (16)	0.0532 (4)
H6	0.4883	0.1188	0.2818	0.064*
C7	0.64323 (12)	0.27161 (16)	0.50763 (12)	0.0387 (3)
C8	0.56922 (15)	0.17868 (18)	0.52523 (15)	0.0506 (4)
H8	0.5671	0.0997	0.4925	0.061*
C9	0.49922 (17)	0.2087 (2)	0.59334 (17)	0.0616 (5)
H9	0.4485	0.1487	0.6068	0.074*
C10	0.50223 (17)	0.3261 (2)	0.64240 (17)	0.0643 (6)
H10	0.4534	0.3435	0.6877	0.077*
C11	0.57600 (16)	0.4172 (2)	0.62521 (15)	0.0548 (5)
H11	0.5778	0.4958	0.6585	0.066*
C12	0.64785 (13)	0.38933 (16)	0.55705 (13)	0.0402 (4)
C13	0.73423 (13)	0.46134 (16)	0.52297 (13)	0.0404 (4)
C14	0.77940 (13)	0.39021 (16)	0.45452 (13)	0.0403 (4)
C15	0.87719 (15)	0.4191 (2)	0.40629 (17)	0.0599 (5)
H15A	0.9096	0.4967	0.4352	0.090*
H15B	0.8568	0.4287	0.3323	0.090*
H15C	0.9282	0.3506	0.4203	0.090*
C16	0.77116 (14)	0.58673 (17)	0.56392 (14)	0.0474 (4)
C17	0.7704 (2)	0.6928 (2)	0.51122 (18)	0.0678 (6)
H17	0.7463	0.6881	0.4399	0.081*
C18	0.8047 (3)	0.8218 (2)	0.5545 (2)	0.0989 (10)
H18A	0.7573	0.8856	0.5198	0.148*
H18B	0.8775	0.8386	0.5434	0.148*
H18C	0.8014	0.8234	0.6278	0.148*
N1	0.72580 (10)	0.26962 (13)	0.44364 (10)	0.0389 (3)
O1	0.68061 (11)	0.05793 (12)	0.36391 (11)	0.0580 (3)
O2	0.80267 (11)	0.20029 (14)	0.28742 (11)	0.0606 (4)
S1	0.70889 (3)	0.18303 (4)	0.33504 (3)	0.04316 (13)
Cl1	0.81805 (5)	0.58714 (5)	0.69822 (4)	0.07334 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0475 (9)	0.0363 (9)	0.0386 (8)	0.0013 (7)	0.0059 (7)	−0.0079 (6)
C2	0.0581 (11)	0.0478 (11)	0.0547 (11)	−0.0050 (8)	0.0061 (9)	0.0042 (8)
C3	0.0830 (16)	0.0484 (12)	0.0628 (13)	0.0038 (10)	−0.0028 (11)	0.0088 (9)
C4	0.0729 (14)	0.0563 (13)	0.0647 (13)	0.0113 (11)	−0.0182 (11)	−0.0081 (10)
C5	0.0532 (12)	0.0609 (14)	0.0768 (15)	−0.0059 (9)	−0.0107 (10)	−0.0115 (11)
C6	0.0562 (11)	0.0432 (10)	0.0575 (11)	−0.0082 (8)	0.0008 (9)	−0.0047 (8)
C7	0.0361 (8)	0.0442 (9)	0.0353 (8)	−0.0018 (6)	0.0041 (6)	0.0017 (6)
C8	0.0532 (10)	0.0487 (11)	0.0502 (10)	−0.0107 (8)	0.0086 (8)	0.0016 (8)
C9	0.0551 (11)	0.0723 (14)	0.0602 (12)	−0.0187 (10)	0.0178 (9)	0.0050 (10)
C10	0.0534 (11)	0.0863 (16)	0.0586 (12)	−0.0065 (10)	0.0260 (10)	−0.0055 (11)
C11	0.0534 (11)	0.0625 (12)	0.0507 (11)	−0.0006 (9)	0.0147 (8)	−0.0114 (9)
C12	0.0381 (8)	0.0443 (9)	0.0372 (8)	−0.0003 (6)	0.0030 (6)	0.0004 (6)
C13	0.0393 (8)	0.0400 (9)	0.0403 (8)	−0.0028 (6)	0.0009 (6)	0.0010 (6)
C14	0.0367 (8)	0.0443 (9)	0.0392 (8)	−0.0053 (6)	0.0032 (6)	0.0018 (6)
C15	0.0452 (10)	0.0750 (14)	0.0617 (12)	−0.0163 (9)	0.0151 (9)	−0.0058 (10)
C16	0.0464 (9)	0.0449 (10)	0.0484 (10)	−0.0041 (7)	−0.0008 (7)	−0.0033 (7)
C17	0.0869 (16)	0.0502 (13)	0.0620 (13)	−0.0157 (10)	−0.0022 (11)	0.0037 (9)
C18	0.147 (3)	0.0493 (15)	0.094 (2)	−0.0298 (15)	−0.0015 (18)	0.0022 (12)
N1	0.0374 (7)	0.0413 (8)	0.0381 (7)	−0.0024 (5)	0.0059 (5)	−0.0021 (5)
O1	0.0720 (9)	0.0340 (7)	0.0679 (9)	0.0075 (6)	0.0105 (7)	−0.0009 (6)
O2	0.0519 (8)	0.0711 (10)	0.0631 (9)	0.0087 (6)	0.0228 (6)	−0.0116 (7)
S1	0.0456 (2)	0.0383 (2)	0.0463 (2)	0.00578 (16)	0.00928 (17)	−0.00582 (17)
Cl1	0.1009 (4)	0.0574 (3)	0.0532 (3)	−0.0016 (3)	−0.0152 (3)	−0.0087 (2)

Geometric parameters (Å, º) top

C1—C6	1.379 (2)	C11—C12	1.387 (2)
C1—C2	1.382 (2)	C11—H11	0.9300
C1—S1	1.7541 (17)	C12—C13	1.444 (2)
C2—C3	1.376 (3)	C13—C14	1.350 (2)
C2—H2	0.9300	C13—C16	1.467 (2)
C3—C4	1.374 (3)	C14—N1	1.429 (2)
C3—H3	0.9300	C14—C15	1.490 (2)
C4—C5	1.359 (3)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.382 (3)	C15—H15C	0.9600
C5—H5	0.9300	C16—C17	1.306 (3)
C6—H6	0.9300	C16—Cl1	1.7517 (18)
C7—C8	1.388 (2)	C17—C18	1.502 (3)
C7—C12	1.389 (2)	C17—H17	0.9300
C7—N1	1.4229 (19)	C18—H18A	0.9600
C8—C9	1.374 (3)	C18—H18B	0.9600
C8—H8	0.9300	C18—H18C	0.9600
C9—C10	1.385 (3)	N1—S1	1.6634 (14)
C9—H9	0.9300	O1—S1	1.4251 (14)
C10—C11	1.371 (3)	O2—S1	1.4207 (13)
C10—H10	0.9300

C6—C1—C2	121.21 (17)	C7—C12—C13	107.68 (14)
C6—C1—S1	119.95 (14)	C14—C13—C12	108.79 (15)
C2—C1—S1	118.82 (14)	C14—C13—C16	126.44 (15)
C3—C2—C1	118.84 (19)	C12—C13—C16	124.58 (15)
C3—C2—H2	120.6	C13—C14—N1	108.47 (14)
C1—C2—H2	120.6	C13—C14—C15	128.24 (16)
C4—C3—C2	120.3 (2)	N1—C14—C15	122.86 (15)
C4—C3—H3	119.9	C14—C15—H15A	109.5
C2—C3—H3	119.9	C14—C15—H15B	109.5
C5—C4—C3	120.5 (2)	H15A—C15—H15B	109.5
C5—C4—H4	119.8	C14—C15—H15C	109.5
C3—C4—H4	119.8	H15A—C15—H15C	109.5
C4—C5—C6	120.6 (2)	H15B—C15—H15C	109.5
C4—C5—H5	119.7	C17—C16—C13	126.77 (18)
C6—C5—H5	119.7	C17—C16—Cl1	119.57 (15)
C1—C6—C5	118.62 (19)	C13—C16—Cl1	113.66 (13)
C1—C6—H6	120.7	C16—C17—C18	126.4 (2)
C5—C6—H6	120.7	C16—C17—H17	116.8
C8—C7—C12	122.00 (15)	C18—C17—H17	116.8
C8—C7—N1	130.50 (16)	C17—C18—H18A	109.5
C12—C7—N1	107.49 (13)	C17—C18—H18B	109.5
C9—C8—C7	116.92 (18)	H18A—C18—H18B	109.5
C9—C8—H8	121.5	C17—C18—H18C	109.5
C7—C8—H8	121.5	H18A—C18—H18C	109.5
C8—C9—C10	121.70 (18)	H18B—C18—H18C	109.5
C8—C9—H9	119.2	C7—N1—C14	107.56 (13)
C10—C9—H9	119.2	C7—N1—S1	119.61 (11)
C11—C10—C9	121.08 (18)	C14—N1—S1	124.33 (11)
C11—C10—H10	119.5	O2—S1—O1	119.18 (8)
C9—C10—H10	119.5	O2—S1—N1	107.08 (8)
C10—C11—C12	118.48 (18)	O1—S1—N1	106.54 (8)
C10—C11—H11	120.8	O2—S1—C1	109.51 (8)
C12—C11—H11	120.8	O1—S1—C1	109.14 (8)
C11—C12—C7	119.81 (16)	N1—S1—C1	104.32 (7)
C11—C12—C13	132.51 (17)

C6—C1—C2—C3	0.1 (3)	C14—C13—C16—C17	66.3 (3)
S1—C1—C2—C3	−178.03 (16)	C12—C13—C16—C17	−119.2 (2)
C1—C2—C3—C4	−0.5 (3)	C14—C13—C16—Cl1	−114.73 (18)
C2—C3—C4—C5	0.7 (4)	C12—C13—C16—Cl1	59.8 (2)
C3—C4—C5—C6	−0.4 (3)	C13—C16—C17—C18	177.7 (2)
C2—C1—C6—C5	0.2 (3)	Cl1—C16—C17—C18	−1.3 (4)
S1—C1—C6—C5	178.30 (15)	C8—C7—N1—C14	−179.54 (17)
C4—C5—C6—C1	0.0 (3)	C12—C7—N1—C14	−0.88 (17)
C12—C7—C8—C9	0.7 (3)	C8—C7—N1—S1	31.1 (2)
N1—C7—C8—C9	179.20 (18)	C12—C7—N1—S1	−150.22 (12)
C7—C8—C9—C10	−0.1 (3)	C13—C14—N1—C7	1.30 (18)
C8—C9—C10—C11	−0.4 (4)	C15—C14—N1—C7	174.34 (16)
C9—C10—C11—C12	0.2 (3)	C13—C14—N1—S1	148.83 (12)
C10—C11—C12—C7	0.4 (3)	C15—C14—N1—S1	−38.1 (2)
C10—C11—C12—C13	−179.39 (19)	C7—N1—S1—O2	179.44 (12)
C8—C7—C12—C11	−0.9 (3)	C14—N1—S1—O2	35.51 (15)
N1—C7—C12—C11	−179.69 (16)	C7—N1—S1—O1	−51.99 (14)
C8—C7—C12—C13	178.96 (16)	C14—N1—S1—O1	164.08 (13)
N1—C7—C12—C13	0.17 (18)	C7—N1—S1—C1	63.40 (14)
C11—C12—C13—C14	−179.51 (19)	C14—N1—S1—C1	−80.53 (14)
C7—C12—C13—C14	0.65 (19)	C6—C1—S1—O2	143.30 (15)
C11—C12—C13—C16	5.2 (3)	C2—C1—S1—O2	−38.55 (16)
C7—C12—C13—C16	−174.67 (15)	C6—C1—S1—O1	11.19 (17)
C12—C13—C14—N1	−1.20 (18)	C2—C1—S1—O1	−170.66 (13)
C16—C13—C14—N1	174.01 (15)	C6—C1—S1—N1	−102.37 (15)
C12—C13—C14—C15	−173.75 (18)	C2—C1—S1—N1	75.78 (15)
C16—C13—C14—C15	1.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C7/C12–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.39	2.973 (2)	120
C10—H10···O2ⁱ	0.93	2.49	3.364 (2)	157
C5—H5···Cg1ⁱⁱ	0.93	2.82	3.477 (2)	128

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−3/2, −y−1/2, z−3/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C7/C12–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.39	2.973 (2)	120
C10—H10···O2ⁱ	0.93	2.49	3.364 (2)	157
C5—H5···Cg1ⁱⁱ	0.93	2.82	3.477 (2)	128

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−3/2, −y−1/2, z−3/2.

Acknowledgements

The authors wish to acknowledge the SAIF, IIT, Madras, for the data collection.

References

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Volume 69| Part 12| December 2013| Page o1781

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