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Acta Cryst. (2007). E63, o3698    [ doi:10.1107/S1600536807037415 ]

Ethyl (2-methyl-1-phenylsulfonyl-1H-indole-3-carbonyl)acetate

G. Chakkaravarthi, V. Dhayalan, A. K. Mohanakrishnan and V. Manivannan

Abstract top

In the title compound, C19H17NO5S, the phenyl ring forms a dihedral angle of 83.67 (4)° with the indole ring system. The molecular structure is stabilized by weak intramolecular C-H...O interactions and the crystal packing is stabilized by weak intermolecular C-H...O and C-H...[pi] interactions.

Comment top

Phenylsulfonyl-indole compounds inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells (Williams et al., 1993). Indole-3-carboxylate derivatives exhibit significant antihepatitis B virus activities (Chai et al., 2006).

The geometric parameters in the title compound (Fig. 1) agree with the reported values of similar structures (Liu et al., 2007; Senthil Kumar et al., 2006). The phenyl ring forms dihedral angle of 83.67 (4)° with the indole ring system. The five- (N1/C7/C8/C9/C14) and six- (C9–C14) membered rings in the indane group are planar, with a dihedral angle of 1.90 (4)° between these rings.

The sum of the bond angles around N1 (359.95°) indicates that N1 is sp2-hybridized. The torsion angles O2—S1—N1—C14 and O1—S1—N1—C7 [−44.24 (14)° and 9.30 (15)°, respectively] indicate the syn conformation of the sulfonyl moiety.

The details of the hydrogen bonding are given in Table 1. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O interactions and C—H···π interactions involving the C1–C6 (centroid Cg1) and N1/C7–C14 (centroid Cg2) rings.

A similar compound with dibromomethyl group has been reported (Rinderspacher et al., 2007).

Related literature top

For releted literature, see: Chai et al. (2006); Liu et al. (2007); Senthil Kumar et al. (2006); Williams et al. (1993). A similar compound with a dibromomethyl group has been reported recently (Rinderspacher et al., 2007).

Experimental top

To a solution of ethyl 2-(2-methyl-1H-indole-3-yl)-2-oxoacetate (10 g, 43.2 mmol) in dry dichloromethane (80 ml) under nitrogen, triethylamine (7.8 ml, 56.2 mmol) followed by dimethyl amino pyridine (0.52 g, 4.2 mmol) were added slowly and stirred at 273 K for 30 min. To this benzenesulfonyl chloride (8.3 ml, 64.9 mmol), dry dichloromethane (10 ml) was slowly added at 273 K for 30 min. Then the reaction mixture was stirred at room temperature and poured over crushed ice and extracted with dichloromethane (3 x 20 ml) and dried with sodium sulfate. The solvent was removed under vacuum. Then the crude product was recrystallized from methanol. Single crystals suitable for X-ray analysis were grown by slow evaporation of a methanol solution at room temperature.

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 aromatic C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2 and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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.
Ethyl (2-methyl-1-phenylsulfonyl-1H-indole-3-carbonyl)acetate top
Crystal data top
C19H17NO5SF000 = 776
Mr = 371.40Dx = 1.410 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 26134 reflections
a = 9.6696 (4) Åθ = 2.6–29.9º
b = 13.1526 (5) ŵ = 0.22 mm−1
c = 13.8048 (5) ÅT = 295 (2) K
β = 94.898 (1)ºBlock, colourless
V = 1749.29 (12) Å30.24 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker Kappa APEXII
diffractometer		6064 independent reflections
Radiation source: fine-focus sealed tube4222 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.025
T = 295(2) Kθmax = 32.0º
ω and φ scansθmin = 2.1º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.929, Tmax = 0.958k = −19→17
25430 measured reflectionsl = −20→19
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)] = 0.050H-atom parameters constrained
wR(F2) = 0.161  w = 1/[σ2(Fo2) + (0.0861P)2 + 0.2836P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
6064 reflectionsΔρmax = 0.64 e Å−3
237 parametersΔρmin = −0.33 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C19H17NO5SV = 1749.29 (12) Å3
Mr = 371.40Z = 4
Monoclinic, P21/nMo Kα
a = 9.6696 (4) ŵ = 0.22 mm−1
b = 13.1526 (5) ÅT = 295 (2) K
c = 13.8048 (5) Å0.24 × 0.20 × 0.20 mm
β = 94.898 (1)º
Data collection top
Bruker Kappa APEXII
diffractometer		6064 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4222 reflections with I > 2σ(I)
Tmin = 0.929, Tmax = 0.958Rint = 0.025
25430 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050237 parameters
wR(F2) = 0.161H-atom parameters constrained
S = 1.06Δρmax = 0.64 e Å−3
6064 reflectionsΔρmin = −0.33 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.22318 (4)0.34233 (3)0.23436 (3)0.04290 (12)
O10.31603 (13)0.42516 (11)0.22844 (9)0.0597 (3)
O20.26854 (14)0.24114 (10)0.21807 (9)0.0583 (3)
O30.05279 (16)0.40881 (12)0.65463 (10)0.0754 (5)
O40.37370 (15)0.46654 (12)0.63655 (13)0.0749 (4)
O50.21527 (16)0.58575 (10)0.66369 (11)0.0693 (4)
N10.17082 (13)0.34280 (9)0.34772 (9)0.0388 (3)
C10.07099 (16)0.36573 (12)0.15947 (10)0.0417 (3)
C20.0143 (2)0.28885 (14)0.10043 (15)0.0578 (4)
H20.05420.22450.10160.069*
C3−0.1034 (2)0.31005 (19)0.03940 (17)0.0715 (6)
H3−0.14220.2597−0.00180.086*
C4−0.1632 (2)0.40435 (17)0.03917 (16)0.0676 (5)
H4−0.24310.4172−0.00140.081*
C5−0.1066 (2)0.47999 (17)0.09798 (16)0.0680 (5)
H5−0.14800.54380.09720.082*
C60.0123 (2)0.46155 (14)0.15871 (13)0.0546 (4)
H60.05200.51280.19830.066*
C70.19316 (14)0.41714 (11)0.42039 (10)0.0371 (3)
C80.12836 (14)0.38506 (11)0.49973 (10)0.0364 (3)
C90.05878 (14)0.29003 (10)0.47616 (10)0.0357 (3)
C10−0.01968 (16)0.22449 (12)0.52925 (11)0.0446 (3)
H10−0.04000.24080.59200.054*
C11−0.06630 (19)0.13474 (13)0.48590 (14)0.0539 (4)
H11−0.11920.09030.51990.065*
C12−0.0356 (2)0.10986 (14)0.39263 (14)0.0564 (4)
H12−0.06810.04870.36550.068*
C130.04189 (19)0.17325 (13)0.33887 (12)0.0500 (4)
H130.06240.15600.27640.060*
C140.08790 (15)0.26386 (11)0.38203 (10)0.0370 (3)
C150.2699 (2)0.51382 (13)0.40713 (13)0.0523 (4)
H15A0.25450.55970.45920.078*
H15B0.23730.54430.34620.078*
H15C0.36740.49970.40750.078*
C160.13428 (16)0.43055 (12)0.59581 (11)0.0440 (3)
C170.25701 (18)0.49730 (13)0.63227 (12)0.0484 (4)
C180.3215 (3)0.6517 (2)0.7133 (2)0.0904 (8)
H18A0.27960.69330.76090.109*
H18B0.39280.61010.74740.109*
C190.3829 (4)0.7157 (2)0.6453 (3)0.1093 (11)
H19A0.43460.67490.60340.164*
H19B0.44400.76340.67970.164*
H19C0.31130.75190.60700.164*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.03753 (19)0.0552 (2)0.03706 (19)0.00035 (15)0.00942 (14)−0.00083 (15)
O10.0494 (6)0.0800 (9)0.0516 (7)−0.0196 (6)0.0145 (5)0.0025 (6)
O20.0546 (7)0.0659 (8)0.0556 (7)0.0185 (6)0.0124 (6)−0.0068 (6)
O30.0830 (10)0.0882 (11)0.0598 (8)−0.0327 (8)0.0346 (7)−0.0305 (7)
O40.0513 (8)0.0735 (10)0.0966 (12)0.0002 (7)−0.0132 (7)−0.0058 (8)
O50.0733 (9)0.0544 (8)0.0792 (10)−0.0107 (6)0.0011 (7)−0.0210 (7)
N10.0429 (6)0.0405 (6)0.0335 (5)−0.0052 (5)0.0057 (5)−0.0013 (5)
C10.0420 (7)0.0498 (8)0.0342 (6)0.0002 (6)0.0075 (5)−0.0003 (6)
C20.0576 (10)0.0490 (9)0.0651 (11)−0.0013 (8)−0.0049 (8)−0.0049 (8)
C30.0626 (12)0.0702 (13)0.0780 (14)−0.0122 (10)−0.0152 (10)−0.0110 (11)
C40.0507 (10)0.0789 (14)0.0708 (13)0.0028 (10)−0.0082 (9)0.0054 (11)
C50.0670 (12)0.0669 (12)0.0688 (12)0.0197 (10)−0.0020 (10)0.0006 (10)
C60.0629 (11)0.0533 (10)0.0470 (9)0.0080 (8)0.0011 (8)−0.0075 (7)
C70.0357 (6)0.0361 (7)0.0392 (7)−0.0022 (5)0.0022 (5)−0.0003 (5)
C80.0362 (6)0.0362 (6)0.0368 (6)−0.0011 (5)0.0032 (5)−0.0026 (5)
C90.0332 (6)0.0374 (7)0.0363 (6)−0.0025 (5)0.0018 (5)−0.0004 (5)
C100.0435 (8)0.0490 (8)0.0419 (7)−0.0093 (6)0.0072 (6)0.0007 (6)
C110.0547 (9)0.0502 (9)0.0570 (10)−0.0180 (7)0.0062 (8)0.0049 (7)
C120.0657 (11)0.0451 (9)0.0575 (10)−0.0182 (8)0.0005 (8)−0.0070 (7)
C130.0599 (10)0.0465 (8)0.0436 (8)−0.0096 (7)0.0049 (7)−0.0082 (6)
C140.0370 (6)0.0371 (7)0.0366 (6)−0.0032 (5)0.0020 (5)0.0000 (5)
C150.0599 (10)0.0434 (8)0.0541 (9)−0.0150 (7)0.0090 (8)0.0007 (7)
C160.0465 (8)0.0431 (8)0.0429 (7)−0.0048 (6)0.0066 (6)−0.0088 (6)
C170.0514 (9)0.0490 (8)0.0435 (8)−0.0063 (7)−0.0031 (7)−0.0027 (7)
C180.114 (2)0.0722 (16)0.0828 (17)−0.0360 (14)−0.0062 (15)−0.0201 (12)
C190.109 (2)0.0856 (19)0.127 (3)−0.0298 (17)−0.028 (2)0.0274 (17)
Geometric parameters (Å, °) top
S1—O11.4185 (13)C8—C91.4433 (19)
S1—O21.4251 (13)C8—C161.452 (2)
S1—N11.6854 (12)C9—C141.3960 (19)
S1—C11.7520 (16)C9—C101.3967 (19)
O3—C161.2130 (19)C10—C111.382 (2)
O4—C171.195 (2)C10—H100.9300
O5—C171.317 (2)C11—C121.385 (3)
O5—C181.468 (3)C11—H110.9300
N1—C71.4042 (18)C12—C131.379 (2)
N1—C141.4178 (18)C12—H120.9300
C1—C61.382 (2)C13—C141.389 (2)
C1—C21.382 (2)C13—H130.9300
C2—C31.385 (3)C15—H15A0.9600
C2—H20.9300C15—H15B0.9600
C3—C41.368 (3)C15—H15C0.9600
C3—H30.9300C16—C171.527 (2)
C4—C51.368 (3)C18—C191.427 (4)
C4—H40.9300C18—H18A0.9700
C5—C61.385 (3)C18—H18B0.9700
C5—H50.9300C19—H19A0.9600
C6—H60.9300C19—H19B0.9600
C7—C81.3738 (19)C19—H19C0.9600
C7—C151.492 (2)
O1—S1—O2120.22 (8)C11—C10—H10120.9
O1—S1—N1107.01 (7)C9—C10—H10120.9
O2—S1—N1105.72 (7)C10—C11—C12121.10 (15)
O1—S1—C1109.57 (8)C10—C11—H11119.4
O2—S1—C1108.98 (8)C12—C11—H11119.4
N1—S1—C1104.09 (6)C13—C12—C11121.79 (16)
C17—O5—C18116.98 (19)C13—C12—H12119.1
C7—N1—C14109.15 (11)C11—C12—H12119.1
C7—N1—S1128.74 (10)C12—C13—C14117.18 (15)
C14—N1—S1122.06 (10)C12—C13—H13121.4
C6—C1—C2121.39 (16)C14—C13—H13121.4
C6—C1—S1119.23 (13)C13—C14—C9121.89 (13)
C2—C1—S1119.36 (13)C13—C14—N1130.91 (13)
C1—C2—C3118.37 (18)C9—C14—N1107.17 (12)
C1—C2—H2120.8C7—C15—H15A109.5
C3—C2—H2120.8C7—C15—H15B109.5
C4—C3—C2120.57 (19)H15A—C15—H15B109.5
C4—C3—H3119.7C7—C15—H15C109.5
C2—C3—H3119.7H15A—C15—H15C109.5
C3—C4—C5120.70 (19)H15B—C15—H15C109.5
C3—C4—H4119.7O3—C16—C8122.50 (15)
C5—C4—H4119.7O3—C16—C17116.49 (14)
C4—C5—C6120.06 (19)C8—C16—C17120.47 (13)
C4—C5—H5120.0O4—C17—O5126.67 (17)
C6—C5—H5120.0O4—C17—C16121.70 (16)
C1—C6—C5118.90 (17)O5—C17—C16111.42 (15)
C1—C6—H6120.6C19—C18—O5110.8 (2)
C5—C6—H6120.6C19—C18—H18A109.5
C8—C7—N1107.63 (12)O5—C18—H18A109.5
C8—C7—C15128.71 (14)C19—C18—H18B109.5
N1—C7—C15123.62 (13)O5—C18—H18B109.5
C7—C8—C9108.77 (12)H18A—C18—H18B108.1
C7—C8—C16128.08 (13)C18—C19—H19A109.5
C9—C8—C16122.96 (13)C18—C19—H19B109.5
C14—C9—C10119.87 (13)H19A—C19—H19B109.5
C14—C9—C8107.22 (12)C18—C19—H19C109.5
C10—C9—C8132.83 (13)H19A—C19—H19C109.5
C11—C10—C9118.15 (15)H19B—C19—H19C109.5
O1—S1—N1—C79.30 (15)C16—C8—C9—C14−173.10 (14)
O2—S1—N1—C7138.55 (13)C7—C8—C9—C10178.99 (16)
C1—S1—N1—C7−106.67 (14)C16—C8—C9—C103.6 (3)
O1—S1—N1—C14−173.50 (12)C14—C9—C10—C110.0 (2)
O2—S1—N1—C14−44.24 (14)C8—C9—C10—C11−176.40 (16)
C1—S1—N1—C1470.53 (13)C9—C10—C11—C120.4 (3)
O1—S1—C1—C6−42.83 (15)C10—C11—C12—C13−0.3 (3)
O2—S1—C1—C6−176.23 (13)C11—C12—C13—C14−0.2 (3)
N1—S1—C1—C671.33 (14)C12—C13—C14—C90.6 (3)
O1—S1—C1—C2135.39 (14)C12—C13—C14—N1178.30 (16)
O2—S1—C1—C21.99 (16)C10—C9—C14—C13−0.5 (2)
N1—S1—C1—C2−110.45 (14)C8—C9—C14—C13176.71 (15)
C6—C1—C2—C30.3 (3)C10—C9—C14—N1−178.69 (13)
S1—C1—C2—C3−177.86 (16)C8—C9—C14—N1−1.45 (16)
C1—C2—C3—C4−1.2 (3)C7—N1—C14—C13−177.75 (16)
C2—C3—C4—C51.1 (4)S1—N1—C14—C134.6 (2)
C3—C4—C5—C6−0.1 (4)C7—N1—C14—C90.18 (16)
C2—C1—C6—C50.7 (3)S1—N1—C14—C9−177.51 (10)
S1—C1—C6—C5178.83 (15)C7—C8—C16—O3165.01 (17)
C4—C5—C6—C1−0.8 (3)C9—C8—C16—O3−20.6 (3)
C14—N1—C7—C81.23 (16)C7—C8—C16—C17−23.7 (2)
S1—N1—C7—C8178.72 (11)C9—C8—C16—C17150.71 (15)
C14—N1—C7—C15−176.61 (14)C18—O5—C17—O4−3.1 (3)
S1—N1—C7—C150.9 (2)C18—O5—C17—C16171.70 (18)
N1—C7—C8—C9−2.13 (16)O3—C16—C17—O4114.6 (2)
C15—C7—C8—C9175.57 (15)C8—C16—C17—O4−57.2 (2)
N1—C7—C8—C16172.93 (14)O3—C16—C17—O5−60.5 (2)
C15—C7—C8—C16−9.4 (3)C8—C16—C17—O5127.69 (16)
C7—C8—C9—C142.26 (16)C17—O5—C18—C1989.1 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O3i0.932.563.197 (2)126
C2—H2···O20.932.522.897 (2)104
C10—H10···O30.932.513.026 (2)115
C13—H13···O20.932.483.001 (2)116
C15—H15B···O10.962.432.798 (2)103
C3—H3···Cg1ii0.932.703.524148
C4—H4···Cg2ii0.932.903.619135
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1/2, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O3i0.932.563.197 (2)126
C2—H2···O20.932.522.897 (2)104
C10—H10···O30.932.513.026 (2)115
C13—H13···O20.932.483.001 (2)116
C15—H15B···O10.962.432.798 (2)103
C3—H3···Cg1ii0.932.703.524148
C4—H4···Cg2ii0.932.903.619135
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1/2, −y+1/2, z−1/2.
Acknowledgements top

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

references
References top

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