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Acta Cryst. (2009). E65, o2069    [ doi:10.1107/S1600536809029985 ]

Ethyl 2-acetoxymethyl-1-phenylsulfonyl-1H-indole-3-carboxylate

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

Abstract top

In the title compound, C20H19NO6S, the phenyl ring of the phenylsulfonyl group makes a dihedral angle of 83.35 (5)° with the indole ring system. The molecular structure exhibits a number of short intramolecular C-H...O contacts.

Comment top

Indole derivatives exhibit antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). Some of the indole alkaloids extracted from plants possess interesting cytotoxic and antiparasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981).

The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Chakkaravarthi et al., 2007, 2008); (Gunasekaran et al., 2009). The phenyl ring makes a dihedral angle of 83.35 (5) ° with the indole ring system. The sum of the bond angles around N1 [356.99 (5)°] indicate the sp2 hybridized state of atom N1 in the molecule.

A distorted tetrahedral geometry [O1—S1—O2 = 120.74 (10) ° and O1—S1—N1 = 106.73 (8) °] around S1 is observed. The widening of the angles may be due to repulsive interactions between the two short S=O bonds. The torsion angles O1—S1—N1—C14 and O2—S1—N1—C7 [20.02 (18) ° and -51.75 (15) ° respectively] indicate the syn conformation of sulfonyl moiety.

The molecular structure is stabilized by weak intramolecular C—H···O interactions. The C6—H6···O2 interaction generate an S(5) graph set motif. The C8—H8···O2, C11—H11···O3, C18—H18A···O4 & C18—H18B···O1 interactions generate S(6) graph set motif and C2—H2···O5 interaction generate an S(8) graph set motif. The C6—H6···O2 and C8—H8···O2 interactions together constitute a pair of bifurcated acceptor bonds generating a ring of graph set R21(9) (Bernstein et al., 1995).

Related literature top

For the biological activity of indole derivatives, see: Andreani et al. (2001); Quetin-Leclercq (1994); Mukhopadhyay et al. (1981); Singh et al. (2000). For related structures, see: Chakkaravarthi et al. (2007, 2008); Gunasekaran et al. (2009); For graph-set notation, see: Bernstein et al. (1995)

Experimental top

Ethyl 2-(bromomethyl)-1-(phenylsulfonyl)-1H-indole-3-carboxylate (1 g, 2.4 mmol) was dissolved in dry dimethylformamide (10 ml). To this potassium acetate (0.47 g, 4.8 mmol) was added under nitrogen atmosphere. The reaction mixture was allowed to stir for 5 hr at room temperature. Then, the reaction mixture was poured over crushed ice (100 g) containing 1 mL of conc. HCl. The precipitated solid was filtered off and the solid was washed with water (3 x 20 ml) and dried. The product was recrystallized from methanol. Yield: 0.7 g (74%), m.p. 361–363K.

Refinement top

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, C—H = 0.97Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96Å 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.
Ethyl 2-acetoxymethyl-1-phenylsulfonyl-1H-indole-3-carboxylate top
Crystal data top
C20H19NO6SF(000) = 1680
Mr = 401.42Dx = 1.427 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 6552 reflections
a = 18.9097 (6) Åθ = 2.7–27.1°
b = 7.9737 (2) ŵ = 0.21 mm−1
c = 24.7877 (7) ÅT = 295 K
V = 3737.50 (18) Å3Block, colourless
Z = 80.25 × 0.20 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer		5788 independent reflections
Radiation source: fine-focus sealed tube3533 reflections with I > 2σ(I)
graphiteRint = 0.031
Detector resolution: 0 pixels mm-1θmax = 31.6°, θmin = 2.0°
ω and φ scansh = −27→20
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −11→8
Tmin = 0.949, Tmax = 0.959l = −36→36
28247 measured reflections
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0697P)2 + 1.0858P]
where P = (Fo2 + 2Fc2)/3
5788 reflections(Δ/σ)max < 0.001
255 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.35 e Å−3
Crystal data top
C20H19NO6SV = 3737.50 (18) Å3
Mr = 401.42Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 18.9097 (6) ŵ = 0.21 mm−1
b = 7.9737 (2) ÅT = 295 K
c = 24.7877 (7) Å0.25 × 0.20 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer		5788 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3533 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 0.959Rint = 0.031
28247 measured reflectionsθmax = 31.6°
Refinement top
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.153Δρmax = 0.28 e Å−3
S = 1.01Δρmin = −0.35 e Å−3
5788 reflectionsAbsolute structure: ?
255 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.68111 (9)0.2922 (2)0.13401 (7)0.0409 (4)
C20.66359 (10)0.3751 (3)0.18121 (7)0.0483 (4)
H20.61650.38790.19130.058*
C30.71703 (11)0.4382 (3)0.21287 (8)0.0541 (5)
H30.70620.49610.24440.065*
C40.78647 (11)0.4159 (3)0.19792 (9)0.0558 (5)
H40.82240.45670.21990.067*
C50.80341 (11)0.3345 (3)0.15112 (9)0.0552 (5)
H50.85060.32140.14130.066*
C60.75066 (11)0.2720 (3)0.11846 (8)0.0483 (4)
H60.76170.21700.08650.058*
C70.60056 (10)0.4924 (2)0.03978 (6)0.0428 (4)
C80.66197 (11)0.4833 (3)0.00964 (7)0.0541 (5)
H80.68950.38680.00880.065*
C90.68026 (13)0.6250 (3)−0.01919 (8)0.0637 (6)
H90.72140.6239−0.03970.076*
C100.63942 (13)0.7675 (3)−0.01839 (8)0.0625 (6)
H100.65350.8601−0.03850.075*
C110.57857 (12)0.7761 (3)0.01128 (7)0.0525 (5)
H110.55110.87290.01140.063*
C120.55875 (10)0.6358 (2)0.04138 (6)0.0430 (4)
C130.49985 (10)0.6010 (2)0.07648 (6)0.0413 (4)
C140.50652 (9)0.4409 (2)0.09542 (6)0.0404 (4)
C150.44401 (11)0.7252 (3)0.08755 (7)0.0494 (5)
C160.33828 (13)0.7855 (4)0.13344 (13)0.0798 (8)
H16A0.32270.83830.10020.096*
H16B0.35330.87270.15820.096*
C170.28112 (17)0.6899 (4)0.15688 (15)0.1048 (11)
H17A0.26380.61060.13090.157*
H17B0.24360.76440.16710.157*
H17C0.29800.63130.18820.157*
C180.45723 (10)0.3415 (3)0.12950 (7)0.0471 (4)
H18A0.40950.38490.12620.057*
H18B0.45730.22500.11820.057*
C190.45014 (11)0.2553 (3)0.22036 (8)0.0537 (5)
C200.48239 (14)0.2728 (4)0.27501 (9)0.0738 (7)
H20A0.45770.20200.30010.111*
H20B0.47890.38740.28660.111*
H20C0.53120.24030.27350.111*
N10.56802 (8)0.37097 (19)0.07288 (6)0.0430 (3)
O10.56787 (8)0.10956 (18)0.12805 (7)0.0627 (4)
O20.64517 (9)0.13016 (19)0.04850 (6)0.0663 (4)
O30.44205 (10)0.8600 (2)0.06699 (8)0.0857 (6)
O40.39629 (8)0.6727 (2)0.12256 (6)0.0641 (4)
O50.48159 (7)0.35577 (17)0.18482 (5)0.0502 (3)
O60.40269 (11)0.1643 (3)0.20854 (7)0.0913 (6)
S10.61405 (3)0.20341 (6)0.09468 (2)0.04808 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0439 (9)0.0323 (10)0.0464 (8)0.0010 (7)−0.0041 (7)0.0052 (7)
C20.0451 (10)0.0481 (12)0.0516 (9)0.0023 (9)0.0002 (8)0.0016 (8)
C30.0603 (12)0.0513 (13)0.0508 (10)−0.0009 (10)−0.0050 (9)−0.0036 (9)
C40.0541 (12)0.0504 (13)0.0631 (11)−0.0073 (9)−0.0138 (9)0.0040 (9)
C50.0441 (10)0.0516 (13)0.0698 (12)−0.0025 (9)0.0003 (9)0.0104 (10)
C60.0504 (10)0.0405 (12)0.0541 (9)0.0027 (8)0.0030 (8)0.0026 (8)
C70.0524 (10)0.0400 (11)0.0359 (7)−0.0054 (8)−0.0076 (7)−0.0011 (7)
C80.0604 (12)0.0565 (13)0.0454 (9)−0.0010 (10)0.0001 (8)−0.0051 (9)
C90.0693 (14)0.0767 (17)0.0452 (10)−0.0160 (12)0.0061 (9)−0.0028 (10)
C100.0826 (15)0.0570 (15)0.0478 (10)−0.0208 (12)−0.0024 (10)0.0080 (9)
C110.0728 (13)0.0397 (12)0.0450 (9)−0.0074 (9)−0.0084 (9)0.0026 (8)
C120.0551 (10)0.0391 (11)0.0348 (7)−0.0054 (8)−0.0106 (7)−0.0035 (7)
C130.0491 (10)0.0381 (10)0.0366 (7)−0.0010 (8)−0.0114 (7)−0.0010 (7)
C140.0420 (9)0.0404 (11)0.0389 (8)−0.0030 (7)−0.0104 (7)0.0011 (7)
C150.0537 (11)0.0463 (13)0.0482 (9)0.0039 (9)−0.0120 (8)0.0002 (8)
C160.0608 (14)0.0734 (19)0.1053 (19)0.0158 (13)0.0051 (14)−0.0091 (15)
C170.084 (2)0.087 (2)0.144 (3)0.0024 (17)0.0415 (19)−0.005 (2)
C180.0438 (9)0.0490 (12)0.0485 (9)−0.0053 (8)−0.0103 (7)0.0048 (8)
C190.0529 (11)0.0520 (13)0.0562 (10)−0.0001 (10)0.0086 (9)0.0086 (9)
C200.0858 (17)0.0825 (18)0.0532 (11)−0.0016 (14)0.0033 (11)0.0150 (12)
N10.0468 (8)0.0363 (9)0.0459 (7)−0.0002 (6)−0.0071 (6)0.0036 (6)
O10.0561 (8)0.0387 (9)0.0933 (11)−0.0070 (6)−0.0113 (8)0.0163 (7)
O20.0780 (10)0.0467 (9)0.0743 (9)0.0083 (7)−0.0106 (8)−0.0226 (7)
O30.0919 (13)0.0588 (12)0.1065 (14)0.0256 (10)0.0135 (11)0.0258 (10)
O40.0605 (9)0.0577 (10)0.0741 (9)0.0132 (7)0.0094 (7)0.0034 (8)
O50.0545 (8)0.0515 (8)0.0445 (6)−0.0091 (6)−0.0059 (6)0.0084 (6)
O60.0865 (12)0.1080 (15)0.0792 (11)−0.0482 (12)0.0073 (10)0.0148 (11)
S10.0519 (3)0.0306 (3)0.0617 (3)0.0003 (2)−0.0106 (2)−0.0024 (2)
Geometric parameters (Å, °) top
C1—C61.380 (3)C13—C151.473 (3)
C1—C21.384 (3)C14—N11.406 (2)
C1—S11.7492 (18)C14—C181.487 (3)
C2—C31.375 (3)C15—O31.190 (3)
C2—H20.9300C15—O41.320 (2)
C3—C41.376 (3)C16—O41.444 (3)
C3—H30.9300C16—C171.445 (4)
C4—C51.367 (3)C16—H16A0.9700
C4—H40.9300C16—H16B0.9700
C5—C61.378 (3)C17—H17A0.9600
C5—H50.9300C17—H17B0.9600
C6—H60.9300C17—H17C0.9600
C7—C81.383 (3)C18—O51.451 (2)
C7—C121.390 (3)C18—H18A0.9700
C7—N11.411 (2)C18—H18B0.9700
C8—C91.380 (3)C19—O61.190 (3)
C8—H80.9300C19—O51.331 (2)
C9—C101.374 (4)C19—C201.492 (3)
C9—H90.9300C20—H20A0.9600
C10—C111.367 (3)C20—H20B0.9600
C10—H100.9300C20—H20C0.9600
C11—C121.396 (3)N1—S11.6838 (16)
C11—H110.9300O1—S11.4166 (15)
C12—C131.440 (3)O2—S11.4136 (16)
C13—C141.366 (3)
C6—C1—C2121.34 (17)O3—C15—O4123.1 (2)
C6—C1—S1119.21 (14)O3—C15—C13123.3 (2)
C2—C1—S1119.39 (14)O4—C15—C13113.56 (17)
C3—C2—C1118.77 (18)O4—C16—C17108.4 (2)
C3—C2—H2120.6O4—C16—H16A110.0
C1—C2—H2120.6C17—C16—H16A110.0
C2—C3—C4120.01 (19)O4—C16—H16B110.0
C2—C3—H3120.0C17—C16—H16B110.0
C4—C3—H3120.0H16A—C16—H16B108.4
C5—C4—C3120.91 (19)C16—C17—H17A109.5
C5—C4—H4119.5C16—C17—H17B109.5
C3—C4—H4119.5H17A—C17—H17B109.5
C4—C5—C6120.04 (19)C16—C17—H17C109.5
C4—C5—H5120.0H17A—C17—H17C109.5
C6—C5—H5120.0H17B—C17—H17C109.5
C5—C6—C1118.91 (18)O5—C18—C14107.23 (14)
C5—C6—H6120.5O5—C18—H18A110.3
C1—C6—H6120.5C14—C18—H18A110.3
C8—C7—C12122.42 (18)O5—C18—H18B110.3
C8—C7—N1130.14 (18)C14—C18—H18B110.3
C12—C7—N1107.44 (16)H18A—C18—H18B108.5
C9—C8—C7116.6 (2)O6—C19—O5122.7 (2)
C9—C8—H8121.7O6—C19—C20126.1 (2)
C7—C8—H8121.7O5—C19—C20111.21 (19)
C10—C9—C8121.9 (2)C19—C20—H20A109.5
C10—C9—H9119.1C19—C20—H20B109.5
C8—C9—H9119.1H20A—C20—H20B109.5
C11—C10—C9121.5 (2)C19—C20—H20C109.5
C11—C10—H10119.3H20A—C20—H20C109.5
C9—C10—H10119.3H20B—C20—H20C109.5
C10—C11—C12118.2 (2)C14—N1—C7108.65 (15)
C10—C11—H11120.9C14—N1—S1127.94 (12)
C12—C11—H11120.9C7—N1—S1120.40 (13)
C7—C12—C11119.40 (18)C15—O4—C16116.42 (19)
C7—C12—C13107.40 (16)C19—O5—C18115.88 (15)
C11—C12—C13133.20 (19)O2—S1—O1120.74 (10)
C14—C13—C12108.42 (16)O2—S1—N1106.44 (9)
C14—C13—C15129.06 (18)O1—S1—N1106.73 (8)
C12—C13—C15122.52 (17)O2—S1—C1108.47 (9)
C13—C14—N1108.09 (16)O1—S1—C1109.60 (9)
C13—C14—C18129.45 (17)N1—S1—C1103.45 (8)
N1—C14—C18122.22 (16)
C6—C1—C2—C30.1 (3)C12—C13—C15—O4−177.13 (16)
S1—C1—C2—C3177.33 (15)C13—C14—C18—O5−97.2 (2)
C1—C2—C3—C4−1.1 (3)N1—C14—C18—O589.02 (19)
C2—C3—C4—C51.5 (3)C13—C14—N1—C70.88 (18)
C3—C4—C5—C6−0.7 (3)C18—C14—N1—C7175.80 (14)
C4—C5—C6—C1−0.4 (3)C13—C14—N1—S1160.98 (12)
C2—C1—C6—C50.7 (3)C18—C14—N1—S1−24.1 (2)
S1—C1—C6—C5−176.58 (15)C8—C7—N1—C14179.48 (17)
C12—C7—C8—C90.1 (3)C12—C7—N1—C14−0.79 (18)
N1—C7—C8—C9179.75 (17)C8—C7—N1—S117.6 (2)
C7—C8—C9—C10−0.5 (3)C12—C7—N1—S1−162.66 (12)
C8—C9—C10—C110.2 (3)O3—C15—O4—C162.7 (3)
C9—C10—C11—C120.4 (3)C13—C15—O4—C16−177.34 (18)
C8—C7—C12—C110.6 (3)C17—C16—O4—C15160.9 (2)
N1—C7—C12—C11−179.20 (14)O6—C19—O5—C18−3.3 (3)
C8—C7—C12—C13−179.84 (16)C20—C19—O5—C18176.40 (18)
N1—C7—C12—C130.40 (18)C14—C18—O5—C19−170.56 (16)
C10—C11—C12—C7−0.8 (3)C14—N1—S1—O2150.20 (15)
C10—C11—C12—C13179.76 (18)C7—N1—S1—O2−51.75 (15)
C7—C12—C13—C140.13 (18)C14—N1—S1—O120.02 (18)
C11—C12—C13—C14179.66 (18)C7—N1—S1—O1178.06 (13)
C7—C12—C13—C15−179.64 (15)C14—N1—S1—C1−95.58 (16)
C11—C12—C13—C15−0.1 (3)C7—N1—S1—C162.47 (14)
C12—C13—C14—N1−0.62 (18)C6—C1—S1—O2−4.02 (18)
C15—C13—C14—N1179.14 (16)C2—C1—S1—O2178.69 (15)
C12—C13—C14—C18−175.05 (16)C6—C1—S1—O1129.69 (16)
C15—C13—C14—C184.7 (3)C2—C1—S1—O1−47.59 (17)
C14—C13—C15—O3−176.9 (2)C6—C1—S1—N1−116.77 (15)
C12—C13—C15—O32.8 (3)C2—C1—S1—N165.94 (16)
C14—C13—C15—O43.1 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O50.932.573.446 (2)157
C6—H6···O20.932.502.875 (3)105
C8—H8···O20.932.422.993 (3)120
C11—H11···O30.932.483.003 (3)116
C18—H18A···O40.972.312.886 (3)117
C18—H18B···O10.972.302.793 (3)111
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O50.932.573.446 (2)157
C6—H6···O20.932.502.875 (3)105
C8—H8···O20.932.422.993 (3)120
C11—H11···O30.932.483.003 (3)116
C18—H18A···O40.972.312.886 (3)117
C18—H18B···O10.972.302.793 (3)111
Acknowledgements top

BG thanks AMET University management, India, for their kind support.

references
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