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Acta Cryst. (2008). E64, o751    [ doi:10.1107/S1600536808007794 ]

4-Bromomethyl-1-phenylsulfonyl-1H-indole

G. Chakkaravarthi, R. Sureshbabu, A. K. Mohanakrishnan and V. Manivannan

Abstract top

In the title molecule, C15H12BrNO2S, the indole mean plane and phenyl ring are nearly orthogonal to each other, forming a dihedral angle of 88.19 (13)°. The Br atom is disordered over two close positions with occupancies of 0.56 (4) and 0.44 (4). The crystal packing exhibits weak intermolecular C-H...[pi] interactions.

Comment top

The indole derivatives are found to possess antibacterial (Okabe and Adachi, 1998) and antitumour (Schollmeyer et al., 1995) activities. In continuation of our studies in indole derivatives, we present the crystal structure of the title compound (I).

The geometric parameters of (I) (Fig. 1) agree with those in the reported structures (Chakkaravarthi et al., 2007; 2008) The indole mean plane and phenyl ring are nearly orthogonal to each other forming a dihedral angle of 88.19 (13)°. The plane of N1/S1/C1 makes the dihedral angles of 84.30 (14)°) and 72.38 (16)°, respectively, with the indole mean plane and phenyl ring. The sum of bond angles around N1 (356.9°) indicates that N1 is sp2-hybridized. The torsion angles C11-C10-S1-O2 [-6.3 (5)°] and C15-C10-S1-O1 [39.4 (5)°] indicate the syn conformation of the sulfonyl moiety.

The crystal packing exhibits weak intermolecular C—H···π interactions, involving the rings C3-C8 (centroid Cg1) and C10-C15 (centroid Cg2) (Table 1).

Related literature top

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

Experimental top

4-(Methyl)-1-(phenylsulfonyl)-1H-indole (1 g, 2.8 m.mol), N-bromo succinimide (0.5 g, 3 m.mol), azobis isobutyro nitrile (50 mg) were dissolved in 50 ml of carbon tetra chloride and refluxed on a waterbath for 2 h, then cooled to the room temperature. Succinimide was filtered off over sodium sulfate. Filtrate was evaporated under reduced pressure. Product was recrystallized from methanol. Yield: 80 %.

Refinement top

H atoms were positioned geometrically and refined using riding model with C-H = 0.93-0.97 Å, and Uiso(H) = 1.2Ueq(C). The Br atom was treated as disordered over two close positions with the occupancies of 0.56 (4) and 0.44 (4), respectively. The distances C4-C5, C10-C11, C11-C12, C12-C13, C13-C14, C14-C15, C15-C10 were restrained to 1.395 (5) Å and the distance C9-Br1A was restrained to 1.91 (10) Å. The positive residual peak 1.26 e Å-3 is located at 1.62 Å from C9; the peak might be the disordered component of Br with small occupancy. It was ignored as showing no any structural or packing consequences.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic labels and 50% probability displacement ellipsoids for non-H atoms. Only major parts of the disordered atoms are drawn.
4-Bromomethyl-1-phenylsulfonyl-1H-indole top
Crystal data top
C15H12BrNO2SF000 = 704
Mr = 350.23Dx = 1.608 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5113 reflections
a = 11.7060 (9) Åθ = 2.5–25.8º
b = 8.2399 (7) ŵ = 2.99 mm−1
c = 15.4495 (11) ÅT = 295 (2) K
β = 103.858 (3)ºBlock, colourless
V = 1446.8 (2) Å30.18 × 0.18 × 0.16 mm
Z = 4
Data collection top
Bruker Kappa APEX2
diffractometer		3606 independent reflections
Radiation source: fine-focus sealed tube2160 reflections with I > 2s(I)
Monochromator: graphiteRint = 0.041
T = 295(2) Kθmax = 28.6º
ω and φ scanθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→15
Tmin = 0.566, Tmax = 0.620k = −10→11
16472 measured reflectionsl = −12→20
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.199  w = 1/[σ2(Fo2) + (0.089P)2 + 1.9138P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3606 reflectionsΔρmax = 1.25 e Å−3
191 parametersΔρmin = −0.54 e Å−3
8 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C15H12BrNO2SV = 1446.8 (2) Å3
Mr = 350.23Z = 4
Monoclinic, P21/cMo Kα
a = 11.7060 (9) ŵ = 2.99 mm−1
b = 8.2399 (7) ÅT = 295 (2) K
c = 15.4495 (11) Å0.18 × 0.18 × 0.16 mm
β = 103.858 (3)º
Data collection top
Bruker Kappa APEX2
diffractometer		3606 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2160 reflections with I > 2s(I)
Tmin = 0.566, Tmax = 0.620Rint = 0.041
16472 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0628 restraints
wR(F2) = 0.199H-atom parameters constrained
S = 1.06Δρmax = 1.25 e Å−3
3606 reflectionsΔρmin = −0.54 e Å−3
191 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.7826 (5)0.6808 (6)0.2167 (3)0.0595 (13)
H10.83450.70220.18100.071*
C20.7274 (4)0.7938 (6)0.2531 (3)0.0576 (12)
H20.73260.90550.24630.069*
C30.6578 (4)0.7104 (6)0.3052 (3)0.0501 (11)
C40.5821 (4)0.7671 (7)0.3555 (3)0.0605 (13)
C50.5258 (5)0.6520 (8)0.3953 (4)0.0771 (18)
H50.47340.68560.42840.092*
C60.5457 (6)0.4882 (9)0.3870 (4)0.0769 (18)
H60.50630.41470.41510.092*
C70.6223 (5)0.4290 (7)0.3385 (4)0.0643 (14)
H70.63670.31860.33450.077*
C80.6757 (4)0.5440 (6)0.2967 (3)0.0489 (11)
C100.9404 (4)0.3588 (5)0.3317 (3)0.0502 (11)
C110.9363 (5)0.2442 (6)0.3965 (3)0.0673 (14)
H110.87540.16900.38840.081*
C121.0253 (5)0.2450 (8)0.4736 (3)0.0833 (19)
H121.02480.16970.51830.100*
C131.1153 (5)0.3580 (7)0.4842 (4)0.0805 (19)
H131.17510.35690.53610.097*
C141.1177 (5)0.4719 (7)0.4194 (3)0.0765 (17)
H141.17830.54770.42770.092*
C151.0293 (4)0.4726 (6)0.3419 (3)0.0621 (13)
H151.02970.54840.29730.075*
N10.7516 (3)0.5255 (5)0.2396 (3)0.0524 (10)
O10.8833 (4)0.3941 (6)0.1596 (2)0.0771 (12)
O20.7575 (3)0.2269 (5)0.2295 (3)0.0775 (11)
S10.83141 (11)0.36176 (16)0.23203 (8)0.0569 (4)
C90.5669 (4)0.9457 (7)0.3700 (3)0.0725 (16)
H9A0.48650.96650.37340.087*0.56 (4)
H9B0.58131.00600.31980.087*0.56 (4)
H9C0.48980.96330.38130.087*0.44 (4)
H9D0.57011.00350.31600.087*0.44 (4)
Br10.6721 (4)1.0180 (7)0.4768 (3)0.0792 (10)0.56 (4)
Br1A0.6841 (7)1.0268 (5)0.4688 (5)0.0844 (16)0.44 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.057 (3)0.061 (3)0.062 (3)0.007 (3)0.017 (2)0.013 (2)
C20.055 (3)0.051 (3)0.066 (3)0.006 (2)0.012 (2)0.010 (2)
C30.047 (2)0.059 (3)0.038 (2)0.008 (2)−0.0024 (18)0.0035 (19)
C40.054 (3)0.081 (4)0.040 (2)0.013 (3)−0.001 (2)0.002 (2)
C50.067 (4)0.115 (6)0.052 (3)0.014 (4)0.020 (3)0.005 (3)
C60.071 (4)0.103 (5)0.059 (3)−0.008 (3)0.019 (3)0.020 (3)
C70.069 (3)0.062 (3)0.056 (3)−0.009 (3)0.005 (3)0.008 (2)
C80.040 (2)0.063 (3)0.037 (2)−0.002 (2)−0.0032 (17)0.0036 (19)
C100.047 (2)0.054 (3)0.046 (2)0.014 (2)0.0038 (19)−0.005 (2)
C110.063 (3)0.065 (3)0.071 (3)0.008 (3)0.009 (3)0.008 (3)
C120.100 (5)0.087 (4)0.057 (3)0.035 (4)0.007 (3)0.015 (3)
C130.072 (4)0.093 (5)0.061 (3)0.030 (4)−0.017 (3)−0.022 (3)
C140.052 (3)0.088 (4)0.079 (4)−0.002 (3)−0.006 (3)−0.019 (3)
C150.054 (3)0.064 (3)0.065 (3)0.000 (3)0.007 (2)−0.002 (2)
N10.049 (2)0.057 (2)0.049 (2)0.0085 (18)0.0068 (17)0.0049 (17)
O10.090 (3)0.096 (3)0.0455 (19)0.027 (2)0.0168 (18)−0.0023 (19)
O20.068 (2)0.062 (2)0.090 (3)0.001 (2)−0.005 (2)−0.014 (2)
S10.0549 (7)0.0595 (8)0.0494 (7)0.0101 (6)−0.0010 (5)−0.0080 (5)
C90.074 (4)0.090 (4)0.050 (3)0.030 (3)0.006 (3)0.002 (3)
Br10.0703 (18)0.118 (3)0.0437 (13)0.035 (2)0.0030 (8)−0.0089 (11)
Br1A0.120 (4)0.059 (2)0.068 (2)−0.016 (3)0.0095 (16)0.0012 (13)
Geometric parameters (Å, °) top
C1—C21.332 (7)C11—C121.381 (4)
C1—N11.398 (7)C11—H110.9300
C1—H10.9300C12—C131.386 (5)
C2—C31.448 (7)C12—H120.9300
C2—H20.9300C13—C141.379 (4)
C3—C41.392 (7)C13—H130.9300
C3—C81.398 (7)C14—C151.382 (4)
C4—C51.380 (4)C14—H140.9300
C4—C91.505 (8)C15—H150.9300
C5—C61.381 (9)N1—S11.661 (4)
C5—H50.9300O1—S11.421 (4)
C6—C71.387 (9)O2—S11.403 (4)
C6—H60.9300C9—Br11.903 (6)
C7—C81.379 (7)C9—Br1A1.9115 (10)
C7—H70.9300C9—H9A0.9700
C8—N11.402 (6)C9—H9B0.9700
C10—C151.381 (4)C9—H9C0.9700
C10—C111.386 (4)C9—H9D0.9700
C10—S11.749 (4)
C2—C1—N1110.6 (4)C12—C13—H13119.4
C2—C1—H1124.7C13—C14—C15119.4 (5)
N1—C1—H1124.7C13—C14—H14120.3
C1—C2—C3107.3 (5)C15—C14—H14120.3
C1—C2—H2126.4C10—C15—C14118.9 (5)
C3—C2—H2126.4C10—C15—H15120.5
C4—C3—C8120.7 (5)C14—C15—H15120.5
C4—C3—C2132.0 (5)C1—N1—C8107.5 (4)
C8—C3—C2107.2 (4)C1—N1—S1122.8 (4)
C5—C4—C3117.0 (5)C8—N1—S1125.8 (3)
C5—C4—C9121.2 (5)O2—S1—O1120.3 (3)
C3—C4—C9121.7 (5)O2—S1—N1107.0 (2)
C4—C5—C6121.4 (6)O1—S1—N1104.9 (2)
C4—C5—H5119.3O2—S1—C10109.2 (2)
C6—C5—H5119.3O1—S1—C10109.7 (2)
C5—C6—C7122.6 (6)N1—S1—C10104.7 (2)
C5—C6—H6118.7C4—C9—Br1111.1 (4)
C7—C6—H6118.7C4—C9—Br1A111.9 (3)
C8—C7—C6115.8 (6)C4—C9—H9A109.4
C8—C7—H7122.1Br1—C9—H9A109.4
C6—C7—H7122.1Br1A—C9—H9A114.5
C7—C8—C3122.4 (5)C4—C9—H9B109.4
C7—C8—N1130.3 (5)Br1—C9—H9B109.4
C3—C8—N1107.3 (4)Br1A—C9—H9B103.3
C15—C10—C11122.4 (4)H9A—C9—H9B108.0
C15—C10—S1117.5 (3)C4—C9—H9C108.8
C11—C10—S1120.1 (3)Br1—C9—H9C103.5
C12—C11—C10118.1 (5)Br1A—C9—H9C108.9
C12—C11—H11121.0H9B—C9—H9C114.5
C10—C11—H11121.0C4—C9—H9D108.7
C11—C12—C13120.0 (5)Br1—C9—H9D116.2
C11—C12—H12120.0Br1A—C9—H9D110.3
C13—C12—H12120.0H9A—C9—H9D101.4
C14—C13—C12121.2 (5)H9C—C9—H9D108.2
C14—C13—H13119.4
N1—C1—C2—C31.5 (6)C13—C14—C15—C100.2 (9)
C1—C2—C3—C4−178.7 (5)C2—C1—N1—C8−2.3 (6)
C1—C2—C3—C8−0.2 (5)C2—C1—N1—S1−161.2 (4)
C8—C3—C4—C5−0.4 (7)C7—C8—N1—C1−179.0 (5)
C2—C3—C4—C5178.0 (5)C3—C8—N1—C12.1 (5)
C8—C3—C4—C9176.4 (4)C7—C8—N1—S1−20.9 (7)
C2—C3—C4—C9−5.2 (7)C3—C8—N1—S1160.2 (3)
C3—C4—C5—C61.3 (8)C1—N1—S1—O2−159.9 (4)
C9—C4—C5—C6−175.5 (5)C8—N1—S1—O245.2 (4)
C4—C5—C6—C7−0.2 (10)C1—N1—S1—O1−31.1 (5)
C5—C6—C7—C8−1.6 (9)C8—N1—S1—O1174.0 (4)
C6—C7—C8—C32.5 (7)C1—N1—S1—C1084.4 (4)
C6—C7—C8—N1−176.3 (5)C8—N1—S1—C10−70.6 (4)
C4—C3—C8—C7−1.5 (7)C15—C10—S1—O2173.1 (4)
C2—C3—C8—C7179.7 (4)C11—C10—S1—O2−6.3 (5)
C4—C3—C8—N1177.5 (4)C15—C10—S1—O139.4 (5)
C2—C3—C8—N1−1.2 (5)C11—C10—S1—O1−140.0 (4)
C15—C10—C11—C12−0.3 (8)C15—C10—S1—N1−72.7 (4)
S1—C10—C11—C12179.0 (4)C11—C10—S1—N1108.0 (4)
C10—C11—C12—C13−0.1 (9)C5—C4—C9—Br184.3 (6)
C11—C12—C13—C140.6 (9)C3—C4—C9—Br1−92.4 (6)
C12—C13—C14—C15−0.6 (9)C5—C4—C9—Br1A91.4 (7)
C11—C10—C15—C140.3 (8)C3—C4—C9—Br1A−85.3 (6)
S1—C10—C15—C14−179.1 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C13—H13···Cg1i0.932.833.716 (6)160
C9—H9D···Cg1ii0.972.923.673 (5)135
C1—H1···Cg2iii0.932.693.584 (6)162
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C13—H13···Cg1i0.932.833.716 (6)160
C9—H9D···Cg1ii0.972.923.673 (5)135
C1—H1···Cg2iii0.932.693.584 (6)162
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2.
Acknowledgements top

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

references
References top

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.

Chakkaravarthi, G., Ramesh, N., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3564.

Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386–387.

Schollmeyer, D., Fischer, G. & Pindur, U. (1995). Acta Cryst. C51, 2572–2575.

Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.