organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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.

Related literature

For the biological activity of indole derivatives, see: Okabe & Adachi (1998[Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386-387.]); Schollmeyer et al. (1995[Schollmeyer, D., Fischer, G. & Pindur, U. (1995). Acta Cryst. C51, 2572-2575.]). For related structures, see: Chakkaravarthi et al. (2007[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.], 2008[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16ClNO2S

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.906, Tmax = 0.938

  • 20036 measured reflections

  • 4705 independent reflections

  • 3357 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.118

  • S = 1.03

  • 4705 reflections

  • 210 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −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 DA 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[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

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

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
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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
C18H16ClNO2SF(000) = 720
Mr = 345.83Dx = 1.363 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6694 reflections
a = 12.5204 (10) Åθ = 2.1–27.9°
b = 10.4962 (7) ŵ = 0.36 mm1
c = 12.983 (1) ÅT = 295 K
β = 98.892 (2)°Block, colourless
V = 1685.7 (2) Å30.28 × 0.24 × 0.18 mm
Z = 4
Data collection top
Bruker Kappa APEXII
diffractometer
4705 independent reflections
Radiation source: fine-focus sealed tube3357 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω and ϕ scanθmax = 29.6°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1717
Tmin = 0.906, Tmax = 0.938k = 148
20036 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.048P)2 + 0.5443P]
where P = (Fo2 + 2Fc2)/3
4705 reflections(Δ/σ)max < 0.001
210 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C18H16ClNO2SV = 1685.7 (2) Å3
Mr = 345.83Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.5204 (10) ŵ = 0.36 mm1
b = 10.4962 (7) ÅT = 295 K
c = 12.983 (1) Å0.28 × 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)
Tmin = 0.906, Tmax = 0.938Rint = 0.032
20036 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.03Δρmax = 0.26 e Å3
4705 reflectionsΔρmin = 0.38 e Å3
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
xyzUiso*/Ueq
C10.59725 (13)0.25271 (15)0.25702 (12)0.0409 (4)
C20.61126 (16)0.36677 (19)0.20771 (15)0.0538 (4)
H20.67910.40460.21400.065*
C30.52304 (19)0.4234 (2)0.14909 (17)0.0662 (6)
H30.53100.50060.11590.079*
C40.42317 (19)0.3664 (2)0.13940 (17)0.0677 (6)
H40.36410.40480.09900.081*
C50.41016 (17)0.2544 (2)0.18844 (18)0.0658 (6)
H50.34210.21700.18170.079*
C60.49712 (15)0.19547 (18)0.24823 (16)0.0532 (4)
H60.48830.11880.28180.064*
C70.64323 (12)0.27161 (16)0.50763 (12)0.0387 (3)
C80.56922 (15)0.17868 (18)0.52523 (15)0.0506 (4)
H80.56710.09970.49250.061*
C90.49922 (17)0.2087 (2)0.59334 (17)0.0616 (5)
H90.44850.14870.60680.074*
C100.50223 (17)0.3261 (2)0.64240 (17)0.0643 (6)
H100.45340.34350.68770.077*
C110.57600 (16)0.4172 (2)0.62521 (15)0.0548 (5)
H110.57780.49580.65850.066*
C120.64785 (13)0.38933 (16)0.55705 (13)0.0402 (4)
C130.73423 (13)0.46134 (16)0.52297 (13)0.0404 (4)
C140.77940 (13)0.39021 (16)0.45452 (13)0.0403 (4)
C150.87719 (15)0.4191 (2)0.40629 (17)0.0599 (5)
H15A0.90960.49670.43520.090*
H15B0.85680.42870.33230.090*
H15C0.92820.35060.42030.090*
C160.77116 (14)0.58673 (17)0.56392 (14)0.0474 (4)
C170.7704 (2)0.6928 (2)0.51122 (18)0.0678 (6)
H170.74630.68810.43990.081*
C180.8047 (3)0.8218 (2)0.5545 (2)0.0989 (10)
H18A0.75730.88560.51980.148*
H18B0.87750.83860.54340.148*
H18C0.80140.82340.62780.148*
N10.72580 (10)0.26962 (13)0.44364 (10)0.0389 (3)
O10.68061 (11)0.05793 (12)0.36391 (11)0.0580 (3)
O20.80267 (11)0.20029 (14)0.28742 (11)0.0606 (4)
S10.70889 (3)0.18303 (4)0.33504 (3)0.04316 (13)
Cl10.81805 (5)0.58714 (5)0.69822 (4)0.07334 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0475 (9)0.0363 (9)0.0386 (8)0.0013 (7)0.0059 (7)0.0079 (6)
C20.0581 (11)0.0478 (11)0.0547 (11)0.0050 (8)0.0061 (9)0.0042 (8)
C30.0830 (16)0.0484 (12)0.0628 (13)0.0038 (10)0.0028 (11)0.0088 (9)
C40.0729 (14)0.0563 (13)0.0647 (13)0.0113 (11)0.0182 (11)0.0081 (10)
C50.0532 (12)0.0609 (14)0.0768 (15)0.0059 (9)0.0107 (10)0.0115 (11)
C60.0562 (11)0.0432 (10)0.0575 (11)0.0082 (8)0.0008 (9)0.0047 (8)
C70.0361 (8)0.0442 (9)0.0353 (8)0.0018 (6)0.0041 (6)0.0017 (6)
C80.0532 (10)0.0487 (11)0.0502 (10)0.0107 (8)0.0086 (8)0.0016 (8)
C90.0551 (11)0.0723 (14)0.0602 (12)0.0187 (10)0.0178 (9)0.0050 (10)
C100.0534 (11)0.0863 (16)0.0586 (12)0.0065 (10)0.0260 (10)0.0055 (11)
C110.0534 (11)0.0625 (12)0.0507 (11)0.0006 (9)0.0147 (8)0.0114 (9)
C120.0381 (8)0.0443 (9)0.0372 (8)0.0003 (6)0.0030 (6)0.0004 (6)
C130.0393 (8)0.0400 (9)0.0403 (8)0.0028 (6)0.0009 (6)0.0010 (6)
C140.0367 (8)0.0443 (9)0.0392 (8)0.0053 (6)0.0032 (6)0.0018 (6)
C150.0452 (10)0.0750 (14)0.0617 (12)0.0163 (9)0.0151 (9)0.0058 (10)
C160.0464 (9)0.0449 (10)0.0484 (10)0.0041 (7)0.0008 (7)0.0033 (7)
C170.0869 (16)0.0502 (13)0.0620 (13)0.0157 (10)0.0022 (11)0.0037 (9)
C180.147 (3)0.0493 (15)0.094 (2)0.0298 (15)0.0015 (18)0.0022 (12)
N10.0374 (7)0.0413 (8)0.0381 (7)0.0024 (5)0.0059 (5)0.0021 (5)
O10.0720 (9)0.0340 (7)0.0679 (9)0.0075 (6)0.0105 (7)0.0009 (6)
O20.0519 (8)0.0711 (10)0.0631 (9)0.0087 (6)0.0228 (6)0.0116 (7)
S10.0456 (2)0.0383 (2)0.0463 (2)0.00578 (16)0.00928 (17)0.00582 (17)
Cl10.1009 (4)0.0574 (3)0.0532 (3)0.0016 (3)0.0152 (3)0.0087 (2)
Geometric parameters (Å, º) top
C1—C61.379 (2)C11—C121.387 (2)
C1—C21.382 (2)C11—H110.9300
C1—S11.7541 (17)C12—C131.444 (2)
C2—C31.376 (3)C13—C141.350 (2)
C2—H20.9300C13—C161.467 (2)
C3—C41.374 (3)C14—N11.429 (2)
C3—H30.9300C14—C151.490 (2)
C4—C51.359 (3)C15—H15A0.9600
C4—H40.9300C15—H15B0.9600
C5—C61.382 (3)C15—H15C0.9600
C5—H50.9300C16—C171.306 (3)
C6—H60.9300C16—Cl11.7517 (18)
C7—C81.388 (2)C17—C181.502 (3)
C7—C121.389 (2)C17—H170.9300
C7—N11.4229 (19)C18—H18A0.9600
C8—C91.374 (3)C18—H18B0.9600
C8—H80.9300C18—H18C0.9600
C9—C101.385 (3)N1—S11.6634 (14)
C9—H90.9300O1—S11.4251 (14)
C10—C111.371 (3)O2—S11.4207 (13)
C10—H100.9300
C6—C1—C2121.21 (17)C7—C12—C13107.68 (14)
C6—C1—S1119.95 (14)C14—C13—C12108.79 (15)
C2—C1—S1118.82 (14)C14—C13—C16126.44 (15)
C3—C2—C1118.84 (19)C12—C13—C16124.58 (15)
C3—C2—H2120.6C13—C14—N1108.47 (14)
C1—C2—H2120.6C13—C14—C15128.24 (16)
C4—C3—C2120.3 (2)N1—C14—C15122.86 (15)
C4—C3—H3119.9C14—C15—H15A109.5
C2—C3—H3119.9C14—C15—H15B109.5
C5—C4—C3120.5 (2)H15A—C15—H15B109.5
C5—C4—H4119.8C14—C15—H15C109.5
C3—C4—H4119.8H15A—C15—H15C109.5
C4—C5—C6120.6 (2)H15B—C15—H15C109.5
C4—C5—H5119.7C17—C16—C13126.77 (18)
C6—C5—H5119.7C17—C16—Cl1119.57 (15)
C1—C6—C5118.62 (19)C13—C16—Cl1113.66 (13)
C1—C6—H6120.7C16—C17—C18126.4 (2)
C5—C6—H6120.7C16—C17—H17116.8
C8—C7—C12122.00 (15)C18—C17—H17116.8
C8—C7—N1130.50 (16)C17—C18—H18A109.5
C12—C7—N1107.49 (13)C17—C18—H18B109.5
C9—C8—C7116.92 (18)H18A—C18—H18B109.5
C9—C8—H8121.5C17—C18—H18C109.5
C7—C8—H8121.5H18A—C18—H18C109.5
C8—C9—C10121.70 (18)H18B—C18—H18C109.5
C8—C9—H9119.2C7—N1—C14107.56 (13)
C10—C9—H9119.2C7—N1—S1119.61 (11)
C11—C10—C9121.08 (18)C14—N1—S1124.33 (11)
C11—C10—H10119.5O2—S1—O1119.18 (8)
C9—C10—H10119.5O2—S1—N1107.08 (8)
C10—C11—C12118.48 (18)O1—S1—N1106.54 (8)
C10—C11—H11120.8O2—S1—C1109.51 (8)
C12—C11—H11120.8O1—S1—C1109.14 (8)
C11—C12—C7119.81 (16)N1—S1—C1104.32 (7)
C11—C12—C13132.51 (17)
C6—C1—C2—C30.1 (3)C14—C13—C16—C1766.3 (3)
S1—C1—C2—C3178.03 (16)C12—C13—C16—C17119.2 (2)
C1—C2—C3—C40.5 (3)C14—C13—C16—Cl1114.73 (18)
C2—C3—C4—C50.7 (4)C12—C13—C16—Cl159.8 (2)
C3—C4—C5—C60.4 (3)C13—C16—C17—C18177.7 (2)
C2—C1—C6—C50.2 (3)Cl1—C16—C17—C181.3 (4)
S1—C1—C6—C5178.30 (15)C8—C7—N1—C14179.54 (17)
C4—C5—C6—C10.0 (3)C12—C7—N1—C140.88 (17)
C12—C7—C8—C90.7 (3)C8—C7—N1—S131.1 (2)
N1—C7—C8—C9179.20 (18)C12—C7—N1—S1150.22 (12)
C7—C8—C9—C100.1 (3)C13—C14—N1—C71.30 (18)
C8—C9—C10—C110.4 (4)C15—C14—N1—C7174.34 (16)
C9—C10—C11—C120.2 (3)C13—C14—N1—S1148.83 (12)
C10—C11—C12—C70.4 (3)C15—C14—N1—S138.1 (2)
C10—C11—C12—C13179.39 (19)C7—N1—S1—O2179.44 (12)
C8—C7—C12—C110.9 (3)C14—N1—S1—O235.51 (15)
N1—C7—C12—C11179.69 (16)C7—N1—S1—O151.99 (14)
C8—C7—C12—C13178.96 (16)C14—N1—S1—O1164.08 (13)
N1—C7—C12—C130.17 (18)C7—N1—S1—C163.40 (14)
C11—C12—C13—C14179.51 (19)C14—N1—S1—C180.53 (14)
C7—C12—C13—C140.65 (19)C6—C1—S1—O2143.30 (15)
C11—C12—C13—C165.2 (3)C2—C1—S1—O238.55 (16)
C7—C12—C13—C16174.67 (15)C6—C1—S1—O111.19 (17)
C12—C13—C14—N11.20 (18)C2—C1—S1—O1170.66 (13)
C16—C13—C14—N1174.01 (15)C6—C1—S1—N1102.37 (15)
C12—C13—C14—C15173.75 (18)C2—C1—S1—N175.78 (15)
C16—C13—C14—C151.5 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N1/C7/C12–C14 ring.
D—H···AD—HH···AD···AD—H···A
C8—H8···O10.932.392.973 (2)120
C10—H10···O2i0.932.493.364 (2)157
C5—H5···Cg1ii0.932.823.477 (2)128
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x3/2, y1/2, z3/2.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the N1/C7/C12–C14 ring.
D—H···AD—HH···AD···AD—H···A
C8—H8···O10.932.392.973 (2)120
C10—H10···O2i0.932.493.364 (2)157
C5—H5···Cg1ii0.932.823.477 (2)128
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x3/2, y1/2, z3/2.
 

Acknowledgements

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

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.  Web of Science CSD CrossRef IUCr Journals
First citationChakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.  Web of Science CSD CrossRef IUCr Journals
First citationOkabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386–387.  Web of Science CSD CrossRef IUCr Journals
First citationSchollmeyer, D., Fischer, G. & Pindur, U. (1995). Acta Cryst. C51, 2572–2575.  CSD CrossRef CAS Web of Science IUCr Journals
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds