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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2916.
Published online 2009 October 31. doi:  10.1107/S1600536809041518
PMCID: PMC2971435

N-[(3-Phenyl­sulfanyl-1-phenyl­sulfonyl-1H-indol-2-yl)meth­yl]propionamide

Abstract

In the title compound, C24H22N2O3S2, the phenyl rings form dihedral angles of 75.2 (1) and 86.1 (1)° with the indole ring system. The mol­ecular structure is stabilized by intra­molecular C–H(...)O and N—H(...)O hydrogen bonds. The crystal structure exhibit inter­molecular N—H(...)O and C—H(...)O hydrogen bonds, C—H(...)π and π–π [centroid–centroid distance = 3.748 (1) Å] inter­actions.

Related literature

For the biological activity of indole derivatives, see: Nieto et al. (2005 [triangle]); Olgen & Coban (2003 [triangle]). For related structures, see: Chakkaravarthi et al. (2007 [triangle], 2008 [triangle]).

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Object name is e-65-o2916-scheme1.jpg

Experimental

Crystal data

  • C24H22N2O3S2
  • M r = 450.56
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2916-efi1.jpg
  • a = 10.9216 (3) Å
  • b = 23.1856 (6) Å
  • c = 9.4298 (2) Å
  • β = 110.147 (1)°
  • V = 2241.74 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 295 K
  • 0.26 × 0.20 × 0.16 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.934, T max = 0.959
  • 26619 measured reflections
  • 5543 independent reflections
  • 3962 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.117
  • S = 1.04
  • 5543 reflections
  • 281 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.24 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041518/gw2070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041518/gw2070Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

In continuation of our studies of indole derivatives, which are known to exhibit anti-oxidant (Olgen & Coban, 2003) and antibacterial (Nieto et al., 2005) activities, we report the crystal structure of the title compound (I). The geometric parameters in (I) (Fig. 1) agree with the reported values of similar structures (Chakkaravarthi et al., 2007, 2008).

The phenyl rings C1—C6 and C15—C20 form the dihedral angles of 75.2 (1)° and 86.1 (1)°, respectively, with the indole ring system. The mean planes of the two phenyl rings are inclined at an angle of 78.7 (1)° with respect to each other. A distorted tetrahedral geometry [N1- S1- O1 106.3 (1)° and N1—S1—O2 106.4 (1)°] is observed around S1 atom.

The molecular structure is stabilized by intramolecular C—H···O and N—H···O hydrogen bonds and the crystal structure exhibit intermolecular N—H···O and C—H···O hydrogen bonds, C—H···π (Table 1 and Fig. 2) and π···π [Cg1···Cg3 3.748 (1) Å; symmetry code: -x, -y, -z; Cg1 and Cg3 are the centroids of N1/C7/C8/C9/C14 and C9—C14 rings, respectively] interactions.

Experimental

To a solution of 1-phenylsulfonyl-(3-(phenylthio)-2-bromomethylindole (0.5 g, 1.09 mmol) in dry 1,2-dimethoxyethane (20 ml), ZnBr2 (0.5 g, 2.22 mmol) and propiononitrile (0.24 g, 4.35 mmol) were added. The reaction mixture was then refluxed for 5 hr under N2 atmosphere. It was then poured over ice-water (30 ml) containing 1 ml of conc.HCl, extracted with CHCl3 (3 X 10 ml) and dried (Na2SO4). Removal of solvent followed by recrystallization from CDCl3 afforded the compound.

Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, N—H = 0.86Å and Uiso(H) = 1.2Ueq(N) for N—H, C—H = 0.97Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for CH3.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C24H22N2O3S2F(000) = 944
Mr = 450.56Dx = 1.335 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9917 reflections
a = 10.9216 (3) Åθ = 2.5–27.5°
b = 23.1856 (6) ŵ = 0.27 mm1
c = 9.4298 (2) ÅT = 295 K
β = 110.147 (1)°Block, colourless
V = 2241.74 (10) Å30.26 × 0.20 × 0.16 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer5543 independent reflections
Radiation source: fine-focus sealed tube3962 reflections with I > 2σ(I)
graphiteRint = 0.026
ω and [var phi] scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −14→14
Tmin = 0.934, Tmax = 0.959k = −30→30
26619 measured reflectionsl = −12→12

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0466P)2 + 0.7649P] where P = (Fo2 + 2Fc2)/3
5543 reflections(Δ/σ)max < 0.001
281 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.24 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.35657 (17)0.09160 (9)0.2609 (2)0.0566 (5)
C20.3938 (2)0.03731 (10)0.3194 (3)0.0700 (6)
H20.35480.02030.38240.084*
C30.4893 (2)0.00865 (12)0.2834 (3)0.0863 (8)
H30.5157−0.02790.32260.104*
C40.5455 (2)0.03392 (15)0.1901 (4)0.0951 (9)
H40.61010.01440.16600.114*
C50.5080 (3)0.08729 (16)0.1321 (4)0.1013 (9)
H50.54660.10390.06830.122*
C60.4135 (2)0.11678 (12)0.1672 (3)0.0823 (7)
H60.38820.15340.12800.099*
C70.02638 (16)0.12894 (7)0.03684 (18)0.0424 (4)
C8−0.08307 (16)0.09744 (7)−0.02800 (17)0.0408 (4)
C9−0.08564 (16)0.05099 (7)0.07163 (18)0.0400 (4)
C10−0.17279 (18)0.00610 (8)0.0598 (2)0.0505 (4)
H10−0.24750.0026−0.02520.061*
C11−0.1468 (2)−0.03292 (9)0.1756 (3)0.0603 (5)
H11−0.2040−0.06330.16900.072*
C12−0.0360 (2)−0.02736 (9)0.3024 (2)0.0621 (5)
H12−0.0205−0.05430.37980.075*
C130.0514 (2)0.01642 (9)0.3174 (2)0.0562 (5)
H130.12550.01970.40330.067*
C140.02547 (16)0.05580 (7)0.19997 (18)0.0421 (4)
C15−0.31688 (17)0.15356 (8)−0.1635 (2)0.0486 (4)
C16−0.2896 (2)0.18462 (9)−0.0313 (2)0.0581 (5)
H16−0.20730.18260.04260.070*
C17−0.3848 (3)0.21854 (11)−0.0095 (3)0.0791 (7)
H17−0.36630.23960.07940.095*
C18−0.5068 (3)0.22168 (13)−0.1175 (4)0.0935 (9)
H18−0.57090.2444−0.10130.112*
C19−0.5334 (2)0.19155 (13)−0.2483 (4)0.0920 (8)
H19−0.61560.1942−0.32220.110*
C20−0.4396 (2)0.15706 (10)−0.2721 (3)0.0703 (6)
H20−0.45890.1361−0.36130.084*
C210.0691 (2)0.18028 (8)−0.0289 (2)0.0523 (4)
H21A0.16340.18020.00170.063*
H21B0.03400.1777−0.13820.063*
C22−0.0289 (2)0.27564 (8)−0.0787 (2)0.0547 (5)
C23−0.0686 (3)0.32715 (9)−0.0106 (2)0.0770 (7)
H23A−0.08680.31500.07860.092*
H23B0.00430.35380.02190.092*
C24−0.1833 (3)0.35801 (12)−0.1114 (3)0.0908 (8)
H24A−0.16770.3693−0.20160.136*
H24B−0.19900.3917−0.06100.136*
H24C−0.25810.3331−0.13740.136*
N10.09434 (14)0.10500 (6)0.17978 (16)0.0455 (3)
N20.02720 (17)0.23387 (6)0.01795 (16)0.0538 (4)
H2A0.03910.23890.11210.065*
O10.23581 (16)0.10952 (8)0.44854 (16)0.0793 (5)
O20.24265 (16)0.18788 (7)0.2755 (2)0.0806 (5)
O3−0.04305 (18)0.27293 (7)−0.21278 (15)0.0766 (5)
S10.23448 (5)0.12841 (2)0.30516 (6)0.05906 (16)
S2−0.20032 (5)0.10989 (2)−0.20547 (5)0.05258 (14)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0413 (9)0.0629 (12)0.0571 (11)−0.0080 (8)0.0062 (8)−0.0097 (9)
C20.0551 (12)0.0777 (15)0.0703 (14)0.0019 (11)0.0128 (10)0.0042 (11)
C30.0606 (14)0.0838 (18)0.105 (2)0.0139 (13)0.0163 (14)−0.0022 (15)
C40.0519 (13)0.119 (2)0.117 (2)0.0048 (15)0.0318 (15)−0.0191 (19)
C50.0679 (16)0.122 (3)0.128 (3)−0.0041 (16)0.0524 (17)0.011 (2)
C60.0575 (13)0.0840 (17)0.108 (2)−0.0058 (12)0.0320 (14)0.0118 (14)
C70.0488 (9)0.0427 (9)0.0380 (8)0.0025 (7)0.0179 (7)−0.0070 (7)
C80.0447 (9)0.0437 (9)0.0352 (8)0.0051 (7)0.0150 (7)−0.0045 (7)
C90.0434 (8)0.0399 (8)0.0405 (8)0.0062 (7)0.0194 (7)−0.0052 (6)
C100.0478 (9)0.0498 (10)0.0569 (10)−0.0007 (8)0.0219 (8)−0.0082 (8)
C110.0690 (13)0.0462 (11)0.0784 (14)0.0009 (9)0.0418 (11)0.0024 (10)
C120.0798 (14)0.0528 (11)0.0636 (12)0.0179 (10)0.0373 (11)0.0167 (9)
C130.0605 (11)0.0618 (12)0.0454 (10)0.0146 (9)0.0169 (8)0.0075 (8)
C140.0443 (9)0.0442 (9)0.0400 (8)0.0073 (7)0.0172 (7)−0.0042 (7)
C150.0503 (9)0.0453 (10)0.0469 (9)0.0041 (8)0.0128 (8)0.0105 (8)
C160.0581 (11)0.0572 (12)0.0567 (11)0.0122 (9)0.0169 (9)0.0004 (9)
C170.0856 (16)0.0702 (15)0.0843 (16)0.0264 (13)0.0331 (14)0.0003 (12)
C180.0784 (17)0.0898 (19)0.114 (2)0.0439 (15)0.0348 (17)0.0238 (17)
C190.0615 (14)0.099 (2)0.099 (2)0.0263 (14)0.0062 (14)0.0286 (17)
C200.0635 (13)0.0708 (14)0.0622 (13)0.0088 (11)0.0034 (10)0.0099 (11)
C210.0637 (11)0.0505 (10)0.0496 (10)−0.0055 (9)0.0284 (9)−0.0068 (8)
C220.0824 (14)0.0484 (10)0.0374 (9)−0.0075 (9)0.0258 (9)−0.0033 (8)
C230.130 (2)0.0541 (12)0.0471 (11)0.0132 (13)0.0308 (13)−0.0022 (9)
C240.119 (2)0.0855 (18)0.0672 (15)0.0240 (16)0.0306 (15)0.0015 (13)
N10.0438 (7)0.0509 (8)0.0388 (7)−0.0017 (6)0.0102 (6)−0.0052 (6)
N20.0867 (12)0.0439 (8)0.0348 (7)−0.0055 (8)0.0259 (8)−0.0049 (6)
O10.0732 (10)0.1127 (13)0.0419 (8)0.0004 (9)0.0070 (7)−0.0195 (8)
O20.0718 (10)0.0555 (9)0.0969 (12)−0.0100 (7)0.0064 (9)−0.0252 (8)
O30.1285 (14)0.0722 (10)0.0369 (7)0.0096 (9)0.0383 (8)0.0020 (6)
S10.0518 (3)0.0646 (3)0.0511 (3)−0.0045 (2)0.0054 (2)−0.0177 (2)
S20.0570 (3)0.0629 (3)0.0337 (2)0.0058 (2)0.01022 (18)−0.00357 (19)

Geometric parameters (Å, °)

C1—C61.374 (3)C15—C161.380 (3)
C1—C21.378 (3)C15—C201.381 (3)
C1—S11.750 (2)C15—S21.7748 (19)
C2—C31.374 (3)C16—C171.374 (3)
C2—H20.9300C16—H160.9300
C3—C41.366 (4)C17—C181.372 (4)
C3—H30.9300C17—H170.9300
C4—C51.358 (4)C18—C191.358 (4)
C4—H40.9300C18—H180.9300
C5—C61.370 (4)C19—C201.378 (4)
C5—H50.9300C19—H190.9300
C6—H60.9300C20—H200.9300
C7—C81.354 (2)C21—N21.445 (2)
C7—N11.410 (2)C21—H21A0.9700
C7—C211.489 (3)C21—H21B0.9700
C8—C91.436 (2)C22—O31.222 (2)
C8—S21.7457 (16)C22—N21.326 (2)
C9—C101.389 (2)C22—C231.489 (3)
C9—C141.392 (2)C23—C241.472 (3)
C10—C111.370 (3)C23—H23A0.9700
C10—H100.9300C23—H23B0.9700
C11—C121.383 (3)C24—H24A0.9600
C11—H110.9300C24—H24B0.9600
C12—C131.367 (3)C24—H24C0.9600
C12—H120.9300N1—S11.6699 (14)
C13—C141.388 (2)N2—H2A0.8600
C13—H130.9300O1—S11.4165 (17)
C14—N11.415 (2)O2—S11.4159 (17)
C6—C1—C2120.6 (2)C15—C16—H16120.2
C6—C1—S1119.78 (18)C18—C17—C16120.7 (2)
C2—C1—S1119.61 (18)C18—C17—H17119.7
C3—C2—C1119.2 (2)C16—C17—H17119.7
C3—C2—H2120.4C19—C18—C17119.8 (2)
C1—C2—H2120.4C19—C18—H18120.1
C4—C3—C2120.0 (3)C17—C18—H18120.1
C4—C3—H3120.0C18—C19—C20120.5 (2)
C2—C3—H3120.0C18—C19—H19119.7
C5—C4—C3120.6 (3)C20—C19—H19119.7
C5—C4—H4119.7C19—C20—C15120.0 (2)
C3—C4—H4119.7C19—C20—H20120.0
C4—C5—C6120.4 (3)C15—C20—H20120.0
C4—C5—H5119.8N2—C21—C7112.51 (15)
C6—C5—H5119.8N2—C21—H21A109.1
C5—C6—C1119.2 (3)C7—C21—H21A109.1
C5—C6—H6120.4N2—C21—H21B109.1
C1—C6—H6120.4C7—C21—H21B109.1
C8—C7—N1108.15 (15)H21A—C21—H21B107.8
C8—C7—C21126.70 (16)O3—C22—N2122.52 (18)
N1—C7—C21125.15 (15)O3—C22—C23122.38 (18)
C7—C8—C9108.81 (14)N2—C22—C23115.06 (16)
C7—C8—S2125.86 (14)C24—C23—C22114.89 (19)
C9—C8—S2125.31 (13)C24—C23—H23A108.5
C10—C9—C14119.86 (16)C22—C23—H23A108.5
C10—C9—C8132.61 (16)C24—C23—H23B108.5
C14—C9—C8107.52 (15)C22—C23—H23B108.5
C11—C10—C9118.87 (18)H23A—C23—H23B107.5
C11—C10—H10120.6C23—C24—H24A109.5
C9—C10—H10120.6C23—C24—H24B109.5
C10—C11—C12120.43 (19)H24A—C24—H24B109.5
C10—C11—H11119.8C23—C24—H24C109.5
C12—C11—H11119.8H24A—C24—H24C109.5
C13—C12—C11122.05 (18)H24B—C24—H24C109.5
C13—C12—H12119.0C7—N1—C14108.48 (13)
C11—C12—H12119.0C7—N1—S1126.97 (12)
C12—C13—C14117.57 (18)C14—N1—S1124.54 (12)
C12—C13—H13121.2C22—N2—C21122.54 (15)
C14—C13—H13121.2C22—N2—H2A118.7
C13—C14—C9121.21 (17)C21—N2—H2A118.7
C13—C14—N1131.79 (16)O2—S1—O1120.59 (11)
C9—C14—N1107.00 (14)O2—S1—N1106.35 (9)
C16—C15—C20119.43 (19)O1—S1—N1106.31 (9)
C16—C15—S2123.45 (14)O2—S1—C1108.84 (11)
C20—C15—S2117.10 (16)O1—S1—C1108.57 (10)
C17—C16—C15119.7 (2)N1—S1—C1105.10 (8)
C17—C16—H16120.2C8—S2—C15103.06 (8)
C6—C1—C2—C30.3 (3)C16—C15—C20—C190.3 (3)
S1—C1—C2—C3179.69 (18)S2—C15—C20—C19−178.15 (19)
C1—C2—C3—C4−0.4 (4)C8—C7—C21—N293.9 (2)
C2—C3—C4—C50.0 (4)N1—C7—C21—N2−85.7 (2)
C3—C4—C5—C60.4 (5)O3—C22—C23—C2432.6 (4)
C4—C5—C6—C1−0.4 (5)N2—C22—C23—C24−149.7 (2)
C2—C1—C6—C50.0 (4)C8—C7—N1—C142.10 (18)
S1—C1—C6—C5−179.3 (2)C21—C7—N1—C14−178.23 (15)
N1—C7—C8—C9−1.67 (18)C8—C7—N1—S1−179.39 (12)
C21—C7—C8—C9178.66 (16)C21—C7—N1—S10.3 (2)
N1—C7—C8—S2179.76 (12)C13—C14—N1—C7178.38 (18)
C21—C7—C8—S20.1 (3)C9—C14—N1—C7−1.68 (17)
C7—C8—C9—C10−178.64 (17)C13—C14—N1—S1−0.2 (3)
S2—C8—C9—C10−0.1 (3)C9—C14—N1—S1179.76 (12)
C7—C8—C9—C140.63 (18)O3—C22—N2—C21−3.8 (3)
S2—C8—C9—C14179.21 (12)C23—C22—N2—C21178.51 (19)
C14—C9—C10—C11−0.3 (2)C7—C21—N2—C22−132.61 (19)
C8—C9—C10—C11178.90 (17)C7—N1—S1—O225.25 (18)
C9—C10—C11—C120.4 (3)C14—N1—S1—O2−156.46 (14)
C10—C11—C12—C13−0.2 (3)C7—N1—S1—O1154.92 (15)
C11—C12—C13—C14−0.1 (3)C14—N1—S1—O1−26.79 (16)
C12—C13—C14—C90.2 (3)C7—N1—S1—C1−90.08 (16)
C12—C13—C14—N1−179.87 (18)C14—N1—S1—C188.21 (15)
C10—C9—C14—C130.0 (2)C6—C1—S1—O2−19.4 (2)
C8—C9—C14—C13−179.39 (15)C2—C1—S1—O2161.21 (16)
C10—C9—C14—N1−179.96 (14)C6—C1—S1—O1−152.42 (18)
C8—C9—C14—N10.66 (17)C2—C1—S1—O128.22 (19)
C20—C15—C16—C170.0 (3)C6—C1—S1—N194.15 (19)
S2—C15—C16—C17178.35 (17)C2—C1—S1—N1−85.20 (17)
C15—C16—C17—C180.2 (4)C7—C8—S2—C15−93.53 (16)
C16—C17—C18—C19−0.8 (4)C9—C8—S2—C1588.13 (15)
C17—C18—C19—C201.1 (5)C16—C15—S2—C820.21 (18)
C18—C19—C20—C15−0.9 (4)C20—C15—S2—C8−161.43 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O20.862.522.939 (2)111
C6—H6···O20.932.572.925 (3)103
C13—H13···O10.932.372.921 (3)118
C21—H21A···O20.972.432.849 (3)106
C21—H21B···O30.972.382.767 (2)103
C18—H18···O2i0.932.523.317 (3)144
N2—H2A···O3ii0.862.152.899 (2)145
C16—H16···O3ii0.932.603.416 (3)147
C10—H10···Cg2iii0.932.813.658 (2)152
C5—H5···Cg4iv0.932.913.788 (4)158

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2070).

References

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