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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2733.
Published online 2009 October 17. doi:  10.1107/S1600536809041191
PMCID: PMC2970994

2-Chloro­methyl-3-methyl-1-phenyl­sulfonyl-1H-indole

Abstract

In the title compound, C16H14ClNO2S, the phenyl ring makes a dihedral angle of 78.1 (1)° with the indole ring system. The mol­ecular structure is stabilized by weak intra­molecular C—H(...)O inter­actions. The crystal structure exhibits weak inter­molecular C—H(...)O, C—H(...)π and π–π [centroid–centroid distances = 3.620 (1)–3.794 (1) Å] inter­actions.

Related literature

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

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Object name is e-65-o2733-scheme1.jpg

Experimental

Crystal data

  • C16H14ClNO2S
  • M r = 319.79
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2733-efi1.jpg
  • a = 7.9769 (6) Å
  • b = 10.8064 (9) Å
  • c = 17.3418 (12) Å
  • β = 97.500 (2)°
  • V = 1482.1 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.40 mm−1
  • T = 295 K
  • 0.30 × 0.28 × 0.26 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.889, T max = 0.903
  • 17616 measured reflections
  • 3885 independent reflections
  • 3201 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.120
  • S = 1.04
  • 3885 reflections
  • 191 parameters
  • H-atom parameters constrained
  • Δρmax = 0.59 e Å−3
  • Δρmin = −0.45 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 global, I. DOI: 10.1107/S1600536809041191/is2470sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041191/is2470Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

The indole derivatives are found to possess antibacterial (Okabe & 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 plane of the phenyl ring forms a dihedral angle of 78.1 (1)° with the indole ring system. The torsion angles O2—S1—N1—C7 and O1—S1—N1—C14 [-22.9 (2)° and 54.5 (1)°, respectively] indicate the syn-conformation of the sulfonyl moiety. The sum of bond angles around N1 [355.6 (1)°] indicates that N1 is sp2-hybridized.

The molecular packing is stabilized by weak intramolecular C—H···O interactions and the crystal packing of I (Fig. 2) exhibit weak intermolecular C—H···O, C—H···π (see Table 1) and π–π [Cg1···Cg1(-x, -y, 1 - z) distance of 3.620 (1) Å and Cg1···Cg3 (-x, -y, 1 - z) distance of 3.794 (1) Å interactions. Cg1 and Cg3 are the centroids of the N1/C7–C9/C14 and C9–C14 rings, respectively.

Experimental

A mixture of 1-phenylsulfonyl-2,3-dimethylindole (5 g, 17.5 mmol) and finely powdered NCS (2.56 g, 19.17 mmol) in dry CCl4 (80 ml) containing catalytic amount of benzoyl peroxide (0.1 g) was refluxed for 1 h and cooled. The floated succinimide was filtered off and washed with CCl4 (15 ml). The solvent was then removed completely under vacuo and recrystallized from CDCl3.

Refinement

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

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

C16H14ClNO2SF(000) = 664
Mr = 319.79Dx = 1.433 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8432 reflections
a = 7.9769 (6) Åθ = 2.2–28.8°
b = 10.8064 (9) ŵ = 0.40 mm1
c = 17.3418 (12) ÅT = 295 K
β = 97.500 (2)°Block, colourless
V = 1482.1 (2) Å30.30 × 0.28 × 0.26 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer3885 independent reflections
Radiation source: fine-focus sealed tube3201 reflections with I > 2σ(I)
graphiteRint = 0.024
ω and [var phi] scansθmax = 28.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.889, Tmax = 0.903k = −14→14
17616 measured reflectionsl = −13→23

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) = 0.120H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0606P)2 + 0.5623P] where P = (Fo2 + 2Fc2)/3
3885 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = −0.45 e Å3

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

xyzUiso*/Ueq
C10.2222 (2)0.12567 (15)0.26775 (9)0.0376 (3)
C20.2156 (3)0.03299 (18)0.21251 (11)0.0510 (4)
H20.1172−0.01250.19890.061*
C30.3596 (3)0.0096 (2)0.17795 (12)0.0633 (6)
H30.3576−0.05190.14030.076*
C40.5042 (3)0.0757 (2)0.19847 (13)0.0602 (5)
H40.60060.05730.17580.072*
C50.5086 (3)0.1686 (2)0.25200 (12)0.0554 (5)
H50.60690.21450.26470.067*
C60.3671 (2)0.19466 (18)0.28736 (10)0.0460 (4)
H60.36950.25780.32390.055*
C70.1768 (2)0.16719 (15)0.47207 (10)0.0391 (3)
C80.2587 (2)0.08731 (16)0.52391 (9)0.0408 (4)
C90.2430 (2)−0.03433 (15)0.49110 (9)0.0371 (3)
C100.3019 (3)−0.14938 (18)0.51880 (11)0.0498 (4)
H100.3646−0.15680.56770.060*
C110.2658 (3)−0.25159 (18)0.47269 (13)0.0543 (5)
H110.3054−0.32880.49040.065*
C120.1713 (3)−0.24139 (17)0.40010 (12)0.0503 (4)
H120.1491−0.31210.37000.060*
C130.1090 (2)−0.12916 (16)0.37131 (10)0.0426 (4)
H130.0446−0.12290.32270.051*
C140.14676 (19)−0.02597 (15)0.41808 (9)0.0343 (3)
C150.1467 (3)0.29996 (17)0.48501 (12)0.0530 (5)
H15A0.13760.31300.53960.064*
H15B0.03980.32360.45550.064*
C160.3463 (3)0.1166 (2)0.60340 (11)0.0604 (5)
H16A0.33480.20330.61370.091*
H16B0.46400.09600.60620.091*
H16C0.29630.06940.64140.091*
N10.10231 (17)0.09922 (13)0.40560 (7)0.0370 (3)
O1−0.08880 (16)0.07654 (16)0.28192 (8)0.0602 (4)
O20.0208 (2)0.28227 (14)0.32369 (9)0.0621 (4)
S10.04580 (5)0.15288 (4)0.31625 (2)0.04245 (13)
Cl10.31210 (9)0.39887 (5)0.45712 (4)0.07026 (19)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0415 (8)0.0392 (8)0.0318 (7)0.0045 (6)0.0032 (6)0.0087 (6)
C20.0614 (11)0.0464 (10)0.0462 (9)−0.0100 (9)0.0108 (8)−0.0018 (8)
C30.0900 (16)0.0496 (12)0.0557 (12)−0.0003 (11)0.0294 (11)−0.0080 (9)
C40.0614 (12)0.0649 (13)0.0592 (12)0.0082 (10)0.0270 (10)0.0068 (10)
C50.0454 (9)0.0698 (14)0.0519 (10)−0.0043 (9)0.0090 (8)0.0039 (9)
C60.0467 (9)0.0519 (10)0.0389 (8)−0.0010 (8)0.0040 (7)−0.0004 (7)
C70.0465 (9)0.0336 (8)0.0401 (8)−0.0044 (7)0.0162 (7)−0.0023 (6)
C80.0469 (9)0.0415 (9)0.0347 (7)−0.0092 (7)0.0082 (6)−0.0005 (6)
C90.0391 (8)0.0374 (8)0.0349 (7)−0.0027 (6)0.0058 (6)0.0039 (6)
C100.0539 (10)0.0460 (10)0.0470 (9)0.0006 (8)−0.0025 (8)0.0117 (8)
C110.0630 (12)0.0355 (9)0.0649 (12)0.0069 (8)0.0097 (9)0.0094 (8)
C120.0585 (11)0.0359 (9)0.0579 (11)−0.0027 (8)0.0130 (9)−0.0072 (8)
C130.0474 (9)0.0413 (9)0.0392 (8)−0.0026 (7)0.0057 (7)−0.0033 (7)
C140.0355 (7)0.0338 (8)0.0344 (7)0.0006 (6)0.0081 (6)0.0029 (6)
C150.0683 (12)0.0373 (9)0.0588 (11)−0.0017 (9)0.0279 (9)−0.0040 (8)
C160.0773 (14)0.0624 (13)0.0397 (9)−0.0185 (11)0.0007 (9)−0.0052 (9)
N10.0423 (7)0.0337 (7)0.0354 (6)0.0033 (5)0.0070 (5)0.0039 (5)
O10.0372 (6)0.0834 (11)0.0567 (8)0.0000 (7)−0.0064 (6)0.0106 (7)
O20.0714 (10)0.0515 (9)0.0644 (9)0.0286 (7)0.0124 (7)0.0183 (7)
S10.0366 (2)0.0485 (3)0.0416 (2)0.01086 (17)0.00270 (15)0.01142 (17)
Cl10.0967 (4)0.0386 (3)0.0815 (4)−0.0169 (3)0.0344 (3)−0.0031 (2)

Geometric parameters (Å, °)

C1—C61.380 (3)C10—C111.372 (3)
C1—C21.382 (3)C10—H100.9300
C1—S11.7559 (17)C11—C121.385 (3)
C2—C31.387 (3)C11—H110.9300
C2—H20.9300C12—C131.379 (3)
C3—C41.364 (3)C12—H120.9300
C3—H30.9300C13—C141.389 (2)
C4—C51.365 (3)C13—H130.9300
C4—H40.9300C14—N11.408 (2)
C5—C61.382 (3)C15—Cl11.812 (2)
C5—H50.9300C15—H15A0.9700
C6—H60.9300C15—H15B0.9700
C7—C81.352 (2)C16—H16A0.9600
C7—N11.429 (2)C16—H16B0.9600
C7—C151.477 (2)C16—H16C0.9600
C8—C91.431 (2)N1—S11.6607 (13)
C8—C161.496 (2)O1—S11.4216 (15)
C9—C101.392 (2)O2—S11.4206 (15)
C9—C141.395 (2)
C6—C1—C2121.15 (17)C12—C11—H11119.5
C6—C1—S1119.29 (13)C13—C12—C11121.79 (18)
C2—C1—S1119.53 (14)C13—C12—H12119.1
C1—C2—C3118.21 (19)C11—C12—H12119.1
C1—C2—H2120.9C12—C13—C14117.02 (17)
C3—C2—H2120.9C12—C13—H13121.5
C4—C3—C2120.80 (19)C14—C13—H13121.5
C4—C3—H3119.6C13—C14—C9121.98 (15)
C2—C3—H3119.6C13—C14—N1130.59 (15)
C3—C4—C5120.56 (19)C9—C14—N1107.42 (13)
C3—C4—H4119.7C7—C15—Cl1113.22 (13)
C5—C4—H4119.7C7—C15—H15A108.9
C4—C5—C6120.1 (2)Cl1—C15—H15A108.9
C4—C5—H5119.9C7—C15—H15B108.9
C6—C5—H5119.9Cl1—C15—H15B108.9
C1—C6—C5119.14 (18)H15A—C15—H15B107.7
C1—C6—H6120.4C8—C16—H16A109.5
C5—C6—H6120.4C8—C16—H16B109.5
C8—C7—N1108.80 (14)H16A—C16—H16B109.5
C8—C7—C15126.40 (17)C8—C16—H16C109.5
N1—C7—C15124.29 (16)H16A—C16—H16C109.5
C7—C8—C9108.21 (15)H16B—C16—H16C109.5
C7—C8—C16127.22 (17)C14—N1—C7107.46 (13)
C9—C8—C16124.53 (17)C14—N1—S1120.74 (11)
C10—C9—C14119.47 (16)C7—N1—S1127.36 (12)
C10—C9—C8132.44 (16)O2—S1—O1120.13 (10)
C14—C9—C8108.08 (14)O2—S1—N1106.45 (8)
C11—C10—C9118.82 (17)O1—S1—N1106.64 (8)
C11—C10—H10120.6O2—S1—C1109.81 (9)
C9—C10—H10120.6O1—S1—C1108.11 (9)
C10—C11—C12120.91 (18)N1—S1—C1104.57 (7)
C10—C11—H11119.5
C6—C1—C2—C31.0 (3)C10—C9—C14—N1179.02 (15)
S1—C1—C2—C3−176.87 (15)C8—C9—C14—N1−0.22 (18)
C1—C2—C3—C40.5 (3)C8—C7—C15—Cl191.1 (2)
C2—C3—C4—C5−1.8 (4)N1—C7—C15—Cl1−98.03 (19)
C3—C4—C5—C61.6 (3)C13—C14—N1—C7−179.07 (16)
C2—C1—C6—C5−1.2 (3)C9—C14—N1—C71.18 (17)
S1—C1—C6—C5176.64 (15)C13—C14—N1—S1−21.1 (2)
C4—C5—C6—C1−0.1 (3)C9—C14—N1—S1159.16 (11)
N1—C7—C8—C91.60 (19)C8—C7—N1—C14−1.75 (17)
C15—C7—C8—C9173.60 (16)C15—C7—N1—C14−173.96 (15)
N1—C7—C8—C16−176.32 (18)C8—C7—N1—S1−157.84 (13)
C15—C7—C8—C16−4.3 (3)C15—C7—N1—S130.0 (2)
C7—C8—C9—C10−179.98 (19)C14—N1—S1—O2−176.12 (13)
C16—C8—C9—C10−2.0 (3)C7—N1—S1—O2−22.86 (16)
C7—C8—C9—C14−0.87 (19)C14—N1—S1—O154.50 (14)
C16—C8—C9—C14177.12 (17)C7—N1—S1—O1−152.24 (14)
C14—C9—C10—C111.1 (3)C14—N1—S1—C1−59.89 (14)
C8—C9—C10—C11−179.89 (19)C7—N1—S1—C193.37 (15)
C9—C10—C11—C12−0.6 (3)C6—C1—S1—O243.32 (16)
C10—C11—C12—C13−0.3 (3)C2—C1—S1—O2−138.81 (15)
C11—C12—C13—C140.6 (3)C6—C1—S1—O1176.10 (14)
C12—C13—C14—C9−0.1 (2)C2—C1—S1—O1−6.02 (17)
C12—C13—C14—N1−179.82 (17)C6—C1—S1—N1−70.55 (15)
C10—C9—C14—C13−0.8 (2)C2—C1—S1—N1107.33 (15)
C8—C9—C14—C13180.00 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.512.886 (3)104
C13—H13···O10.932.473.033 (2)119
C15—H15B···O20.972.312.853 (3)114
C2—H2···O2i0.932.483.314 (2)149
C16—H16A···Cg2ii0.962.943.777 (2)146
C16—H16B···Cg3iii0.962.923.781 (3)149

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2470).

References

  • 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]
  • 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. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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