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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o392.
Published online 2008 January 9. doi:  10.1107/S1600536807068778
PMCID: PMC2960260

Ethyl 2-[(phenyl­sulfan­yl)meth­yl]-1-(phenyl­sulfon­yl)-1H-indole-3-carboxyl­ate

Abstract

In the title compound, C24H21NO4S2, the phenyl rings form dihedral angles of 85.77 (9) and 85.22 (9)° and the ester group forms an angle of 12.61 (10)° with the indane ring. The mol­ecular structure is stabilized by weak intra­molecular C—H(...)O inter­actions.

Related literature

For related literature, see: Allen et al. (1987 [triangle]); Nieto et al. (2005 [triangle]); Satis Kumar et al. (2006 [triangle]). A similar compound has been reported by Chakkaravarthi et al. (2007 [triangle]).

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Object name is e-64-0o392-scheme1.jpg

Experimental

Crystal data

  • C24H21NO4S2
  • M r = 451.56
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o392-efi1.jpg
  • a = 11.745 (1) Å
  • b = 7.7140 (2) Å
  • c = 26.770 (1) Å
  • β = 116.020 (2)°
  • V = 2179.6 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 295 (2) K
  • 0.24 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEX2 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.927, T max = 0.947
  • 9731 measured reflections
  • 4116 independent reflections
  • 2128 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.122
  • S = 0.82
  • 4116 reflections
  • 281 parameters
  • 9 restraints
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.18 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068778/rk2072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068778/rk2072Isup2.hkl

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

supplementary crystallographic information

Comment

The benzenesulfonamide derivatives exhibit significant biological activities, such as antibacterial (Nieto et al., 2005). In the molecule of title compound (I) (Fig. 1), the bond lengths and angles are agree with the reported similar structures (Allen et al. 1987; Chakkaravarthi et al., 2007; Satis Kumar et al., 2006).

The phenyl rings C1–C6 and C19–C24 form the dihedral angles with the indane ring system of 85.77 (9)° and 85.22 (9)°, respectively. The dihedral angle between these phenyl rings is 4.26 (9)°. The ester group C16/O3/O4/C17/C18 forms a dihedral angle with the indane ring system of 12.61 (10)°.

The molecular structure of (I) (Fig. 1) is stabilized by intramolecular C—H···O interactions. A similar compound has been reported by Chakkaravarthi et al. (2007).

Experimental

To a well stirred suspension of sodium hydride (0.17 g, 3.55 mmol) in dry tetrahydrofurane (THF) (10 ml) at 273 K, a solution of thiophenol (0.36 ml, 3.55 mmol) in dry THF (10 ml) was slowly added over a period of 10 min. After the evaluation of hydrogen gas ceased a solution of ethyl 2-(bromomethyl)-1-(phenylsulfonyl)-1H-indole-3-carboxylate (1 g, 2.36 mmol) in dry THF (10 ml) was added in dropwise with vigorous stirring. Then the reaction mixture was stirred for 2 h and then poured over crushed ice. The precipitated solid was filtered, washed with water and dried over calcium chloride. The crude sulfide was recrystallized from methanol. Single crystals suitable for X-ray analysis were grown by slow evaporation of a methanol solution at room temperature.

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 CH, 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. The bond distances C19—C20, C19—24, C20—C21, C21—C22, C22—C23, C23—C24, C3—C4, C4—C5 and C5—C6 were restrained to be 1.39 (3) Å and the bond distance C17—C18 was restrained to be 1.55 (3) Å.

Figures

Fig. 1.
The molecular structure of (I), with atom labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Intramolecular H-bonds are shown as dotted lines.

Crystal data

C24H21NO4S2F000 = 944
Mr = 451.56Dx = 1.376 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10291 reflections
a = 11.745 (1) Åθ = 2.8–26.0º
b = 7.7140 (2) ŵ = 0.28 mm1
c = 26.770 (1) ÅT = 295 (2) K
β = 116.020 (2)ºBlock, colourless
V = 2179.6 (2) Å30.24 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEX2 diffractometer4116 independent reflections
Radiation source: fine-focus sealed tube2128 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 295(2) Kθmax = 28.7º
ω– and [var phi]–scanθmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.927, Tmax = 0.947k = −10→8
9731 measured reflectionsl = −36→35

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.122  w = 1/[σ2(Fo2) + (0.0481P)2] where P = (Fo2 + 2Fc2)/3
S = 0.82(Δ/σ)max < 0.001
4116 reflectionsΔρmax = 0.23 e Å3
281 parametersΔρmin = −0.18 e Å3
9 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All s.u.'s (except the s.u.'s in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
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 > 2σ(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)

xyzUiso*/Ueq
S10.75890 (7)0.46511 (8)0.02189 (3)0.03776 (17)
S21.06434 (7)0.72740 (9)0.09115 (4)0.0563 (2)
O10.84440 (19)0.5349 (2)0.00269 (8)0.0471 (5)
O20.64341 (19)0.5547 (2)0.01066 (8)0.0494 (5)
O31.2184 (2)0.3917 (3)0.22110 (10)0.0725 (6)
O41.11279 (18)0.3805 (3)0.27290 (8)0.0545 (5)
N10.8387 (2)0.4502 (2)0.09151 (9)0.0362 (5)
C11.2195 (3)0.7980 (3)0.13616 (12)0.0438 (6)
C21.2297 (3)0.9673 (4)0.15435 (13)0.0546 (7)
H21.15701.03290.14570.066*
C31.3477 (3)1.0396 (4)0.18538 (15)0.0661 (9)
H31.35371.15430.19700.079*
C41.4568 (3)0.9438 (4)0.19933 (15)0.0700 (10)
H41.53600.99270.22030.084*
C51.4459 (3)0.7738 (4)0.18144 (14)0.0628 (9)
H51.51840.70700.19110.075*
C61.3281 (2)0.7019 (4)0.14923 (13)0.0552 (7)
H61.32210.58860.13640.066*
C71.0649 (2)0.4937 (3)0.10300 (12)0.0423 (6)
H7A1.04530.43250.06850.051*
H7B1.14860.45810.13000.051*
C80.9695 (2)0.4468 (3)0.12382 (11)0.0362 (6)
C90.9929 (2)0.4064 (3)0.17792 (10)0.0367 (6)
C100.8719 (2)0.3803 (3)0.17934 (11)0.0368 (6)
C110.8367 (3)0.3384 (4)0.22147 (12)0.0470 (6)
H110.89780.32360.25790.056*
C120.7090 (3)0.3194 (4)0.20795 (13)0.0539 (7)
H120.68480.29030.23560.065*
C130.6167 (3)0.3430 (4)0.15376 (13)0.0513 (7)
H130.53180.32990.14590.062*
C140.6486 (3)0.3858 (3)0.11120 (12)0.0431 (6)
H140.58710.40080.07490.052*
C150.7775 (2)0.4055 (3)0.12549 (10)0.0358 (5)
C161.1197 (3)0.3927 (3)0.22444 (12)0.0442 (6)
C171.2305 (3)0.3585 (4)0.32177 (12)0.0626 (8)
H17A1.29320.44010.32160.075*
H17B1.26270.24190.32330.075*
C181.2026 (4)0.3919 (5)0.37179 (13)0.0733 (10)
H18A1.17880.51100.37170.110*
H18B1.27700.36760.40550.110*
H18C1.13460.31820.36940.110*
C190.7233 (2)0.2500 (3)−0.00112 (10)0.0379 (5)
C200.8218 (3)0.1388 (3)0.00635 (12)0.0507 (7)
H200.90540.17550.02540.061*
C210.7946 (3)−0.0279 (3)−0.01486 (13)0.0594 (9)
H210.8597−0.1040−0.01050.071*
C220.6695 (3)−0.0800 (4)−0.04255 (13)0.0607 (9)
H220.6507−0.1915−0.05710.073*
C230.5720 (3)0.0317 (3)−0.04881 (15)0.0663 (9)
H230.4885−0.0057−0.06740.080*
C240.5977 (2)0.1988 (3)−0.02768 (14)0.0576 (8)
H240.53260.2739−0.03120.069*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0378 (4)0.0385 (3)0.0341 (4)−0.0018 (3)0.0132 (3)0.0011 (3)
S20.0334 (4)0.0581 (4)0.0664 (6)−0.0052 (3)0.0118 (4)0.0160 (4)
O10.0506 (12)0.0494 (10)0.0405 (11)−0.0102 (9)0.0194 (11)0.0004 (8)
O20.0432 (12)0.0476 (10)0.0507 (13)0.0090 (8)0.0146 (11)0.0063 (9)
O30.0350 (12)0.1220 (18)0.0579 (15)0.0079 (12)0.0179 (12)0.0098 (13)
O40.0348 (11)0.0834 (14)0.0379 (11)−0.0033 (10)0.0092 (10)0.0114 (10)
N10.0306 (11)0.0451 (10)0.0327 (12)−0.0052 (9)0.0136 (11)−0.0034 (9)
C10.0366 (15)0.0576 (16)0.0390 (15)−0.0023 (12)0.0183 (14)0.0082 (12)
C20.0505 (19)0.0595 (17)0.0534 (19)0.0039 (14)0.0223 (18)0.0035 (14)
C30.072 (3)0.0648 (19)0.065 (2)−0.0187 (18)0.032 (2)−0.0098 (17)
C40.051 (2)0.097 (3)0.056 (2)−0.0244 (18)0.019 (2)−0.0037 (19)
C50.0363 (16)0.084 (2)0.067 (2)−0.0003 (15)0.0225 (18)0.0078 (17)
C60.0403 (17)0.0656 (18)0.064 (2)−0.0032 (14)0.0267 (17)−0.0010 (15)
C70.0326 (15)0.0515 (13)0.0454 (16)−0.0013 (11)0.0195 (15)0.0035 (12)
C80.0307 (14)0.0386 (12)0.0393 (15)−0.0014 (10)0.0154 (13)−0.0002 (10)
C90.0312 (14)0.0415 (12)0.0368 (15)−0.0044 (10)0.0142 (13)−0.0031 (10)
C100.0331 (14)0.0396 (12)0.0380 (15)−0.0005 (10)0.0160 (13)−0.0026 (11)
C110.0418 (16)0.0620 (16)0.0353 (15)−0.0069 (13)0.0151 (14)−0.0027 (12)
C120.0500 (18)0.0751 (18)0.0461 (18)−0.0146 (15)0.0298 (17)−0.0089 (14)
C130.0359 (16)0.0649 (17)0.059 (2)−0.0088 (13)0.0263 (16)−0.0090 (15)
C140.0309 (14)0.0548 (14)0.0408 (16)−0.0034 (11)0.0132 (14)−0.0052 (12)
C150.0363 (14)0.0374 (12)0.0349 (14)−0.0072 (10)0.0166 (13)−0.0060 (10)
C160.0366 (15)0.0502 (14)0.0431 (16)−0.0009 (11)0.0150 (15)0.0036 (12)
C170.0382 (17)0.086 (2)0.0483 (19)−0.0086 (15)0.0052 (17)0.0149 (17)
C180.060 (2)0.103 (3)0.045 (2)−0.0090 (19)0.0121 (19)0.0156 (17)
C190.0389 (15)0.0421 (12)0.0274 (13)0.0013 (11)0.0095 (13)0.0045 (10)
C200.0489 (18)0.0488 (15)0.0510 (18)−0.0011 (12)0.0186 (17)−0.0036 (13)
C210.068 (2)0.0468 (15)0.057 (2)0.0111 (15)0.021 (2)0.0027 (14)
C220.079 (3)0.0418 (15)0.0470 (19)−0.0043 (15)0.014 (2)0.0021 (13)
C230.051 (2)0.0597 (18)0.067 (2)−0.0175 (15)0.007 (2)−0.0056 (16)
C240.0490 (19)0.0538 (16)0.062 (2)−0.0009 (13)0.0170 (18)−0.0037 (15)

Geometric parameters (Å, °)

S1—O11.4195 (18)C10—C151.393 (4)
S1—O21.4318 (19)C10—C111.398 (4)
S1—N11.683 (2)C11—C121.388 (4)
S1—C191.755 (2)C11—H110.9300
S2—C11.773 (3)C12—C131.390 (4)
S2—C71.830 (3)C12—H120.9300
O3—C161.201 (3)C13—C141.386 (4)
O4—C161.338 (3)C13—H130.9300
O4—C171.437 (3)C14—C151.398 (4)
N1—C81.394 (3)C14—H140.9300
N1—C151.427 (3)C17—C181.533 (3)
C1—C61.381 (4)C17—H17A0.9700
C1—C21.381 (4)C17—H17B0.9700
C2—C31.383 (4)C18—H18A0.9600
C2—H20.9300C18—H18B0.9600
C3—C41.381 (3)C18—H18C0.9600
C3—H30.9300C19—C201.383 (2)
C4—C51.383 (3)C19—C241.385 (2)
C4—H40.9300C20—C211.385 (2)
C5—C61.385 (3)C20—H200.9300
C5—H50.9300C21—C221.383 (4)
C6—H60.9300C21—H210.9300
C7—C81.498 (3)C22—C231.382 (3)
C7—H7A0.9700C22—H220.9300
C7—H7B0.9700C23—C241.387 (3)
C8—C91.386 (3)C23—H230.9300
C9—C101.453 (3)C24—H240.9300
C9—C161.467 (4)
O1—S1—O2119.78 (11)C10—C11—H11120.6
O1—S1—N1106.73 (11)C11—C12—C13121.1 (3)
O2—S1—N1106.35 (11)C11—C12—H12119.4
O1—S1—C19109.19 (11)C13—C12—H12119.4
O2—S1—C19108.93 (11)C14—C13—C12121.4 (3)
N1—S1—C19104.79 (10)C14—C13—H13119.3
C1—S2—C7105.10 (12)C12—C13—H13119.3
C16—O4—C17116.6 (2)C13—C14—C15116.8 (3)
C8—N1—C15109.02 (19)C13—C14—H14121.6
C8—N1—S1127.98 (17)C15—C14—H14121.6
C15—N1—S1122.05 (17)C10—C15—C14122.9 (2)
C6—C1—C2119.4 (3)C10—C15—N1107.4 (2)
C6—C1—S2124.5 (2)C14—C15—N1129.8 (2)
C2—C1—S2115.7 (2)O3—C16—O4122.9 (3)
C1—C2—C3120.1 (3)O3—C16—C9126.2 (3)
C1—C2—H2119.9O4—C16—C9110.9 (2)
C3—C2—H2119.9O4—C17—C18106.6 (2)
C4—C3—C2120.9 (3)O4—C17—H17A110.4
C4—C3—H3119.6C18—C17—H17A110.4
C2—C3—H3119.6O4—C17—H17B110.4
C3—C4—C5118.7 (3)C18—C17—H17B110.4
C3—C4—H4120.7H17A—C17—H17B108.6
C5—C4—H4120.7C17—C18—H18A109.5
C4—C5—C6120.8 (3)C17—C18—H18B109.5
C4—C5—H5119.6H18A—C18—H18B109.5
C6—C5—H5119.6C17—C18—H18C109.5
C1—C6—C5120.1 (3)H18A—C18—H18C109.5
C1—C6—H6120.0H18B—C18—H18C109.5
C5—C6—H6120.0C20—C19—C24122.2 (2)
C8—C7—S2110.86 (17)C20—C19—S1118.70 (18)
C8—C7—H7A109.5C24—C19—S1119.09 (17)
S2—C7—H7A109.5C19—C20—C21119.2 (3)
C8—C7—H7B109.5C19—C20—H20120.4
S2—C7—H7B109.5C21—C20—H20120.4
H7A—C7—H7B108.1C22—C21—C20119.3 (3)
C9—C8—N1108.2 (2)C22—C21—H21120.3
C9—C8—C7127.3 (2)C20—C21—H21120.3
N1—C8—C7124.4 (2)C23—C22—C21120.8 (3)
C8—C9—C10108.1 (2)C23—C22—H22119.6
C8—C9—C16124.4 (2)C21—C22—H22119.6
C10—C9—C16127.5 (2)C22—C23—C24120.6 (3)
C15—C10—C11119.0 (2)C22—C23—H23119.7
C15—C10—C9107.3 (2)C24—C23—H23119.7
C11—C10—C9133.8 (3)C19—C24—C23117.8 (2)
C12—C11—C10118.8 (3)C19—C24—H24121.1
C12—C11—H11120.6C23—C24—H24121.1
O1—S1—N1—C8−20.4 (2)C11—C12—C13—C140.2 (4)
O2—S1—N1—C8−149.37 (19)C12—C13—C14—C15−0.5 (4)
C19—S1—N1—C895.3 (2)C11—C10—C15—C14−1.9 (3)
O1—S1—N1—C15171.99 (17)C9—C10—C15—C14178.2 (2)
O2—S1—N1—C1543.0 (2)C11—C10—C15—N1178.6 (2)
C19—S1—N1—C15−72.3 (2)C9—C10—C15—N1−1.3 (2)
C7—S2—C1—C634.8 (3)C13—C14—C15—C101.4 (4)
C7—S2—C1—C2−151.5 (2)C13—C14—C15—N1−179.3 (2)
C6—C1—C2—C30.0 (4)C8—N1—C15—C102.0 (2)
S2—C1—C2—C3−174.0 (2)S1—N1—C15—C10171.65 (15)
C1—C2—C3—C4−0.9 (5)C8—N1—C15—C14−177.5 (2)
C2—C3—C4—C50.3 (5)S1—N1—C15—C14−7.8 (3)
C3—C4—C5—C61.3 (5)C17—O4—C16—O3−2.5 (4)
C2—C1—C6—C51.5 (4)C17—O4—C16—C9177.3 (2)
S2—C1—C6—C5175.0 (2)C8—C9—C16—O3−10.4 (4)
C4—C5—C6—C1−2.2 (5)C10—C9—C16—O3169.3 (3)
C1—S2—C7—C8119.3 (2)C8—C9—C16—O4169.8 (2)
C15—N1—C8—C9−1.9 (2)C10—C9—C16—O4−10.5 (3)
S1—N1—C8—C9−170.77 (17)C16—O4—C17—C18166.6 (3)
C15—N1—C8—C7−177.4 (2)O1—S1—C19—C2048.4 (2)
S1—N1—C8—C713.7 (3)O2—S1—C19—C20−179.2 (2)
S2—C7—C8—C9−103.3 (3)N1—S1—C19—C20−65.7 (2)
S2—C7—C8—N171.4 (3)O1—S1—C19—C24−129.6 (2)
N1—C8—C9—C101.1 (3)O2—S1—C19—C242.9 (3)
C7—C8—C9—C10176.5 (2)N1—S1—C19—C24116.4 (2)
N1—C8—C9—C16−179.2 (2)C24—C19—C20—C212.1 (4)
C7—C8—C9—C16−3.8 (4)S1—C19—C20—C21−175.8 (2)
C8—C9—C10—C150.2 (3)C19—C20—C21—C22−0.6 (4)
C16—C9—C10—C15−179.6 (2)C20—C21—C22—C23−0.6 (5)
C8—C9—C10—C11−179.7 (3)C21—C22—C23—C240.3 (5)
C16—C9—C10—C110.6 (4)C20—C19—C24—C23−2.3 (5)
C15—C10—C11—C121.5 (4)S1—C19—C24—C23175.6 (2)
C9—C10—C11—C12−178.6 (3)C22—C23—C24—C191.0 (5)
C10—C11—C12—C13−0.7 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7A···O10.972.382.813 (4)107
C7—H7B···O30.972.262.977 (4)130
C11—H11···O40.932.422.932 (3)115
C14—H14···O20.932.412.966 (3)119
C24—H24···O20.932.522.898 (3)105

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2072).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2004). APEX2 Version 1.0-27. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chakkaravarthi, G., Ramesh, N., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3564.
  • Nieto, M. J., Alovero, F. L., Manzo, R. H. & Mazzieri, M. R. (2005). Eur. J. Med. Chem.40, 361–369. [PubMed]
  • Satis Kumar, B. K., Gayathri, D., Velmurugan, D., Ravikumar, K. & Poornachandran, M. (2006). Acta Cryst. E62, o5388–o5389.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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