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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2957.
Published online 2010 October 30. doi:  10.1107/S160053681004198X
PMCID: PMC3009294

(4-Bromo­phen­yl)(1-phenyl­sulfonyl-1H-indol-2-yl)methanone

Abstract

In the title compound, C21H14BrNO3S, the indole ring system forms dihedral angles of 65.64 (8) and 59.30 (8)°, respectively, with the phenyl and bromo­phenyl rings. In the crystal, mol­ecules are connected by a C—H(...)O hydrogen bond, forming a chain along [101]. The chains are further connected by weak inter­molecular C—H(...)π inter­actions, forming a layer parallel to the ac plane.

Related literature

For the biological activity of indole derivatives, see: Joshi & Chand (1982 [triangle]); Pomarnacka & Kozlarska-Kedra (2003 [triangle]); Poter et al. (1977 [triangle]). For related structures, see: Chakkaravarthi et al. (2007 [triangle], 2008 [triangle]). For details of the configuration at the S atom, see: Bassindale (1984 [triangle]). For details of N-atom hybridization, see: Beddoes et al. (1986 [triangle]).

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Object name is e-66-o2957-scheme1.jpg

Experimental

Crystal data

  • C21H14BrNO3S
  • M r = 440.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2957-efi1.jpg
  • a = 8.482 (3) Å
  • b = 25.780 (4) Å
  • c = 8.690 (3) Å
  • β = 93.388 (3)°
  • V = 1896.9 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.30 mm−1
  • T = 295 K
  • 0.24 × 0.22 × 0.20 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.609, T max = 0.656
  • 18123 measured reflections
  • 4736 independent reflections
  • 2944 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.111
  • S = 1.03
  • 4736 reflections
  • 244 parameters
  • H-atom parameters constrained
  • Δρmax = 0.62 e Å−3
  • Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; 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 I, global. DOI: 10.1107/S160053681004198X/is2617sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004198X/is2617Isup2.hkl

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

Acknowledgments

The authors wish to acknowledge DV University of Madras for the data collection.

supplementary crystallographic information

Comment

Indole derivatives are found abundantly in a variety of natural plants (Poter et al., 1977). Compounds containing the indole moiety exhibit antibacterial and fungicidal activities (Joshi & Chand, 1982). Indole derivatives are also known to exhibit anticancer and anti - HIV (Pomarnacka & Kozlarska-Kedra, 2003) activities.

In continuation of our studies of indole derivatives, we determined the crystal structure of the title compound,(I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported values for similar structures (Chakkaravarthi et al., 2007, 2008). Due to Thorpe–Ignold effect (Bassindale, 1984), bond angles around atom S1 show significant deviation from ideal tetrahedral value, with significant deviations in angles O2—S1—O1 [120.86 (13)°] and N1—S1—C1 [103.79 (11)°].

The phenyl ring forms the dihedral angle of 65.64 (8)° with the indole ring system and the bromophenyl ring makes the dihedral angle of 59.30 (8)° with the indole ring system. The N1—S1—C1 plane is almost orthogonal to both [dihedral angle 72.30 (9)°] indole ring and [dihedral angle 71.68 (12)°] phenyl ring.

The sum of the bond angles around N1 [341.7 (2)°] indicates that N1 atom is sp3 hybridized (Beddoes et al., 1986). The crystal packing is stabilized by weak intermolecular C—H···O and C—H···π [C4—H4···Cg1 (-1 + x, y, z) distance of 3.635 (4)Å and C4—H4···Cg2 (-1 + x, y, z) distance of 3.681 (4)Å (Cg1 and Cg2 are the centroids of the rings defined by the atoms N1/C7/C8/C9/C14 and C9—C14, respectively] interactions.

Experimental

To a solution of N-(2-Formylphenyl)benzenesulfonamide (0.5 g, 1.91 mmol) in dry CH3CN (20 ml), K2CO3 (0.8 g, 5.79 mmol), 2-bromo-1-(4-bromophenyl)ethanone (0.63 g, 2.26 mmol) were added. The reaction mixture was stirred at room temperature for 6 h under N2 atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml), extracted with chloroform (3 × 10 ml) and dried (Na2SO4). Removal of solvent followed by the residue was dissolved in CH3CN (20 ml), Conc. HCl (3 ml) was added. The reaction mixture was then refluxed for 2 h. It was then poured over ice-water (50 ml), extracted with CHCl3 (3 × 10 ml) and dried (Na2SO4). Removal of solvent followed by crystallization from methanol afforded the compound as a colourless crystal.

Refinement

H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and with Uiso(H) = 1.2Ueq(C).

Figures

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

Crystal data

C21H14BrNO3SF(000) = 888
Mr = 440.30Dx = 1.542 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4249 reflections
a = 8.482 (3) Åθ = 2.5–24.4°
b = 25.780 (4) ŵ = 2.30 mm1
c = 8.690 (3) ÅT = 295 K
β = 93.388 (3)°Block, colourless
V = 1896.9 (10) Å30.24 × 0.22 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer4736 independent reflections
Radiation source: fine-focus sealed tube2944 reflections with I > 2σ(I)
graphiteRint = 0.035
ω and [var phi] scansθmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→11
Tmin = 0.609, Tmax = 0.656k = −29→34
18123 measured reflectionsl = −9→11

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0445P)2 + 0.6759P] where P = (Fo2 + 2Fc2)/3
4736 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.62 e Å3
0 restraintsΔρmin = −0.46 e Å3

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

xyzUiso*/Ueq
Br10.24312 (5)0.018422 (12)0.53534 (5)0.09126 (18)
S10.26404 (8)0.34303 (3)0.83609 (7)0.04855 (18)
O10.3198 (2)0.38893 (8)0.9118 (2)0.0648 (5)
O20.2576 (3)0.29550 (8)0.9169 (2)0.0737 (6)
O30.5440 (2)0.24395 (7)0.8349 (2)0.0671 (6)
N10.3837 (2)0.33357 (7)0.6910 (2)0.0421 (5)
C10.0793 (3)0.35548 (11)0.7418 (3)0.0494 (6)
C20.0204 (4)0.40492 (12)0.7428 (4)0.0703 (9)
H20.07510.43120.79650.084*
C3−0.1230 (4)0.41519 (17)0.6619 (5)0.0963 (12)
H3−0.16370.44870.65860.116*
C4−0.2035 (4)0.3756 (2)0.5872 (5)0.1035 (14)
H4−0.30000.38240.53470.124*
C5−0.1456 (4)0.32696 (18)0.5883 (4)0.0901 (12)
H5−0.20210.30060.53690.108*
C6−0.0021 (4)0.31602 (12)0.6658 (3)0.0650 (8)
H60.03860.28250.66650.078*
C70.4047 (3)0.28357 (9)0.6256 (3)0.0410 (5)
C80.4166 (3)0.28833 (10)0.4728 (3)0.0488 (6)
H80.43150.26120.40450.059*
C90.4027 (3)0.34192 (10)0.4327 (3)0.0477 (6)
C100.4108 (4)0.36829 (14)0.2933 (4)0.0706 (9)
H100.42630.35050.20240.085*
C110.3955 (4)0.42089 (15)0.2939 (4)0.0827 (11)
H110.40030.43910.20190.099*
C120.3731 (4)0.44741 (12)0.4272 (5)0.0769 (10)
H120.36290.48330.42300.092*
C130.3650 (3)0.42278 (11)0.5686 (4)0.0613 (7)
H130.34940.44100.65870.074*
C140.3816 (3)0.36928 (9)0.5669 (3)0.0438 (6)
C150.4561 (3)0.23788 (10)0.7209 (3)0.0471 (6)
C160.4037 (3)0.18560 (9)0.6675 (3)0.0430 (6)
C170.2741 (3)0.17786 (10)0.5660 (3)0.0486 (6)
H170.21870.20620.52440.058*
C180.2266 (3)0.12794 (11)0.5260 (3)0.0566 (7)
H180.13890.12260.45840.068*
C190.3100 (3)0.08671 (10)0.5870 (3)0.0566 (7)
C200.4411 (4)0.09344 (11)0.6858 (4)0.0656 (8)
H200.49800.06500.72460.079*
C210.4865 (3)0.14285 (10)0.7260 (3)0.0586 (7)
H210.57440.14780.79360.070*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1039 (3)0.04279 (18)0.1244 (4)−0.01215 (17)−0.0165 (2)−0.00695 (18)
S10.0576 (4)0.0482 (4)0.0396 (3)0.0031 (3)0.0004 (3)−0.0035 (3)
O10.0676 (13)0.0651 (12)0.0596 (11)0.0067 (10)−0.0144 (10)−0.0246 (10)
O20.0985 (17)0.0670 (13)0.0573 (12)0.0100 (11)0.0197 (11)0.0186 (10)
O30.0788 (14)0.0531 (11)0.0650 (12)0.0036 (10)−0.0339 (11)−0.0042 (9)
N10.0464 (12)0.0357 (10)0.0439 (11)0.0020 (9)−0.0010 (9)0.0010 (8)
C10.0446 (15)0.0566 (15)0.0475 (14)−0.0042 (12)0.0073 (12)−0.0093 (12)
C20.0522 (18)0.066 (2)0.092 (2)0.0062 (15)−0.0045 (16)−0.0181 (17)
C30.059 (2)0.103 (3)0.125 (3)0.022 (2)−0.008 (2)−0.009 (3)
C40.045 (2)0.163 (5)0.102 (3)−0.002 (3)−0.0044 (19)−0.031 (3)
C50.054 (2)0.129 (4)0.088 (3)−0.031 (2)0.0063 (18)−0.041 (2)
C60.0609 (19)0.0685 (19)0.0671 (19)−0.0180 (15)0.0171 (16)−0.0198 (15)
C70.0391 (13)0.0378 (12)0.0452 (14)0.0000 (10)−0.0038 (10)−0.0029 (10)
C80.0482 (15)0.0539 (15)0.0439 (15)−0.0019 (12)−0.0018 (12)−0.0090 (12)
C90.0382 (14)0.0604 (16)0.0438 (14)−0.0065 (12)−0.0029 (11)0.0067 (12)
C100.071 (2)0.086 (2)0.0539 (18)−0.0102 (17)−0.0008 (15)0.0200 (16)
C110.079 (2)0.095 (3)0.073 (2)−0.014 (2)−0.0080 (18)0.041 (2)
C120.067 (2)0.0518 (17)0.110 (3)−0.0056 (15)−0.0073 (19)0.0329 (19)
C130.0565 (18)0.0475 (15)0.079 (2)−0.0009 (13)−0.0005 (15)0.0073 (14)
C140.0349 (13)0.0428 (13)0.0533 (15)−0.0032 (10)−0.0025 (11)0.0084 (11)
C150.0449 (14)0.0445 (13)0.0508 (15)0.0057 (11)−0.0058 (12)−0.0023 (11)
C160.0421 (14)0.0387 (12)0.0475 (14)0.0047 (10)−0.0035 (11)0.0000 (10)
C170.0422 (14)0.0431 (13)0.0590 (16)0.0047 (11)−0.0100 (12)−0.0004 (11)
C180.0470 (16)0.0503 (16)0.0707 (18)−0.0045 (12)−0.0114 (14)−0.0017 (13)
C190.0585 (17)0.0387 (13)0.0719 (19)−0.0029 (12)−0.0005 (14)−0.0020 (12)
C200.071 (2)0.0425 (15)0.080 (2)0.0129 (14)−0.0178 (16)0.0013 (14)
C210.0556 (17)0.0489 (15)0.0685 (18)0.0082 (13)−0.0212 (14)0.0000 (13)

Geometric parameters (Å, °)

Br1—C191.895 (3)C8—H80.9300
S1—O21.415 (2)C9—C141.384 (4)
S1—O11.4211 (19)C9—C101.394 (4)
S1—N11.682 (2)C10—C111.362 (5)
S1—C11.754 (3)C10—H100.9300
O3—C151.215 (3)C11—C121.368 (5)
N1—C141.417 (3)C11—H110.9300
N1—C71.424 (3)C12—C131.388 (4)
C1—C21.369 (4)C12—H120.9300
C1—C61.376 (4)C13—C141.386 (3)
C2—C31.394 (5)C13—H130.9300
C2—H20.9300C15—C161.485 (3)
C3—C41.370 (5)C16—C171.382 (3)
C3—H30.9300C16—C211.387 (3)
C4—C51.346 (6)C17—C181.387 (4)
C4—H40.9300C17—H170.9300
C5—C61.385 (5)C18—C191.367 (4)
C5—H50.9300C18—H180.9300
C6—H60.9300C19—C201.375 (4)
C7—C81.343 (3)C20—C211.370 (4)
C7—C151.490 (3)C20—H200.9300
C8—C91.428 (4)C21—H210.9300
O2—S1—O1120.86 (13)C11—C10—C9118.2 (3)
O2—S1—N1106.80 (11)C11—C10—H10120.9
O1—S1—N1105.58 (12)C9—C10—H10120.9
O2—S1—C1109.31 (14)C10—C11—C12121.2 (3)
O1—S1—C1109.10 (12)C10—C11—H11119.4
N1—S1—C1103.79 (11)C12—C11—H11119.4
C14—N1—C7106.31 (19)C11—C12—C13122.5 (3)
C14—N1—S1119.67 (16)C11—C12—H12118.7
C7—N1—S1121.71 (16)C13—C12—H12118.7
C2—C1—C6121.2 (3)C14—C13—C12115.8 (3)
C2—C1—S1118.9 (2)C14—C13—H13122.1
C6—C1—S1119.9 (2)C12—C13—H13122.1
C1—C2—C3118.8 (3)C9—C14—C13122.3 (2)
C1—C2—H2120.6C9—C14—N1108.3 (2)
C3—C2—H2120.6C13—C14—N1129.4 (2)
C4—C3—C2119.6 (4)O3—C15—C16122.0 (2)
C4—C3—H3120.2O3—C15—C7119.8 (2)
C2—C3—H3120.2C16—C15—C7118.1 (2)
C5—C4—C3121.3 (4)C17—C16—C21119.0 (2)
C5—C4—H4119.4C17—C16—C15122.8 (2)
C3—C4—H4119.4C21—C16—C15118.1 (2)
C4—C5—C6120.2 (3)C16—C17—C18120.2 (2)
C4—C5—H5119.9C16—C17—H17119.9
C6—C5—H5119.9C18—C17—H17119.9
C1—C6—C5119.0 (3)C19—C18—C17119.2 (2)
C1—C6—H6120.5C19—C18—H18120.4
C5—C6—H6120.5C17—C18—H18120.4
C8—C7—N1109.3 (2)C18—C19—C20121.7 (3)
C8—C7—C15125.8 (2)C18—C19—Br1119.3 (2)
N1—C7—C15122.2 (2)C20—C19—Br1119.0 (2)
C7—C8—C9108.6 (2)C21—C20—C19118.8 (3)
C7—C8—H8125.7C21—C20—H20120.6
C9—C8—H8125.7C19—C20—H20120.6
C14—C9—C10120.0 (3)C20—C21—C16121.1 (2)
C14—C9—C8107.5 (2)C20—C21—H21119.4
C10—C9—C8132.5 (3)C16—C21—H21119.4
O2—S1—N1—C14163.63 (18)C10—C11—C12—C130.1 (5)
O1—S1—N1—C14−66.5 (2)C11—C12—C13—C140.2 (5)
C1—S1—N1—C1448.2 (2)C10—C9—C14—C131.2 (4)
O2—S1—N1—C726.6 (2)C8—C9—C14—C13179.6 (2)
O1—S1—N1—C7156.43 (18)C10—C9—C14—N1−177.8 (2)
C1—S1—N1—C7−88.8 (2)C8—C9—C14—N10.6 (3)
O2—S1—C1—C2138.5 (2)C12—C13—C14—C9−0.9 (4)
O1—S1—C1—C24.3 (3)C12—C13—C14—N1177.9 (3)
N1—S1—C1—C2−107.9 (2)C7—N1—C14—C9−0.8 (3)
O2—S1—C1—C6−42.9 (3)S1—N1—C14—C9−143.64 (18)
O1—S1—C1—C6−177.1 (2)C7—N1—C14—C13−179.7 (2)
N1—S1—C1—C670.7 (2)S1—N1—C14—C1337.5 (3)
C6—C1—C2—C3−1.5 (5)C8—C7—C15—O3127.2 (3)
S1—C1—C2—C3177.1 (3)N1—C7—C15—O3−32.1 (4)
C1—C2—C3—C41.8 (6)C8—C7—C15—C16−49.7 (4)
C2—C3—C4—C5−1.1 (7)N1—C7—C15—C16151.0 (2)
C3—C4—C5—C60.0 (6)O3—C15—C16—C17162.2 (3)
C2—C1—C6—C50.5 (4)C7—C15—C16—C17−20.9 (4)
S1—C1—C6—C5−178.1 (2)O3—C15—C16—C21−16.0 (4)
C4—C5—C6—C10.3 (5)C7—C15—C16—C21160.8 (2)
C14—N1—C7—C80.7 (3)C21—C16—C17—C181.2 (4)
S1—N1—C7—C8142.63 (19)C15—C16—C17—C18−177.0 (2)
C14—N1—C7—C15163.0 (2)C16—C17—C18—C19−0.5 (4)
S1—N1—C7—C15−55.1 (3)C17—C18—C19—C20−0.8 (5)
N1—C7—C8—C9−0.4 (3)C17—C18—C19—Br1178.9 (2)
C15—C7—C8—C9−161.9 (2)C18—C19—C20—C211.4 (5)
C7—C8—C9—C14−0.1 (3)Br1—C19—C20—C21−178.3 (2)
C7—C8—C9—C10178.0 (3)C19—C20—C21—C16−0.7 (5)
C14—C9—C10—C11−0.8 (4)C17—C16—C21—C20−0.6 (4)
C8—C9—C10—C11−178.7 (3)C15—C16—C21—C20177.7 (3)
C9—C10—C11—C120.2 (5)

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C7/C8/C9/C14 and C9—C14 rings, respectively
D—H···AD—HH···AD···AD—H···A
C17—H17···O3i0.932.503.383 (3)158
C4—H4···Cg1ii0.932.673.635 (4)127
C4—H4···Cg2ii0.932.763.681 (4)169

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2617).

References

  • Bassindale, A. (1984). The Third Dimension in Organic Chemistry New York: John Wiley and Sons.
  • Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787–797.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.
  • Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542. [PMC free article] [PubMed]
  • Joshi, K. C. & Chand, P. (1982). Pharmazie, 37, 1–12. [PubMed]
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  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
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