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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2906.
Published online 2009 October 28. doi:  10.1107/S1600536809044365
PMCID: PMC2970969

(2-Methyl-1-phenyl­sulfonyl-1H-indol-3-yl)phenyl­methyl acetate

Abstract

In the title compound, C24H21NO4S, the indole ring system makes dihedral angles of 77.8 (1) and 85.4 (1)°, respectively, with the S- and C-bound phenyl rings. The mol­ecular structure is stabilized by a weak intra­molecular C—H(...)O hydrogen bond. In the crystal, a weak inter­molecular C—H(...)O hydrogen bond and a C—H(...)π inter­action are also observed.

Related literature

For the biological activity of indole derivatives, see: Chai et al. (2006 [triangle]); Olgen & Coban (2003 [triangle]). For related structures, see: Chakkaravarthi et al. (2007 [triangle], 2008 [triangle]).

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Object name is e-65-o2906-scheme1.jpg

Experimental

Crystal data

  • C24H21NO4S
  • M r = 419.48
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2906-efi1.jpg
  • a = 14.3655 (6) Å
  • b = 8.3432 (4) Å
  • c = 18.6261 (8) Å
  • β = 108.086 (2)°
  • V = 2122.12 (16) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.18 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 [triangle]) T min = 0.951, T max = 0.968
  • 23327 measured reflections
  • 4712 independent reflections
  • 3030 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.146
  • S = 1.01
  • 4712 reflections
  • 273 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.35 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/S1600536809044365/is2478sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044365/is2478Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

In continuation of our studies of indole derivatives, which are known to exhibit antihepatitis B virus (Chai et al., 2006) and anti-oxidant activity (Olgen & Coban, 2003), we report the crystal structure of the title compound, (I). The bond lengths and bond angles of the title compound are agree with the reported similar structures (Chakkaravarthi et al., 2007,2008).

The phenyl rings C1—C6 and C17—C22 make dihedral angles of 77.8 (1) and 85.4 (1)°, respectively, with the indole ring system. The two phenyl rings are inclined at an angle of 62.2 (1)° with respect to each other. The torsion angles C7—N1—S1—O2 and C14—N1—S1—O1 [-36.8 (2) and 51.1 (2)°, respectively] indicate a syn conformation of the sulfonyl moiety. The sum of the bond angles around N1 [351.2 (2)°] indicates that N1 is sp2-hybridized.

The molecular structure is controlled by a weak intramolecular C—H···O hydrogen bond and the crystal packing of (I) (Fig. 2) is through weak intermolecular C—H···O hydrogen bonds and C—H···π (Table 1) interactions.

Experimental

To a solution of 1-phenylsulfonyl-(2-methyl-1H-indol-3-yl) (phenyl)methanol (0.5 g, 1.32 mmol) in dry DCM (20 ml) acetic anhydride (0.27 g, 2.64 mmol) and pyridine (0.2 g, 2.52 mmol) were added. It was then stirred at room temperature for 7 h under N2 atmosphere. The reaction mixture was poured over crushed ice (100 g) containing 2 ml of Conc. HCl, extracted with CHCl3 (3 × 10 ml) and dried (Na2SO4). Removal of solvent followed by recrystallization from CDCl3 afforded the compound as crystals.

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 = 0.98 Å and Uiso(H) = 1.2Ueq(C) for C—H, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl. The components of the anisotropic displacement parameters in direction of the bond of S1and O2; C3 and C4 were restrained to be equal within an effective standard deviation of 0.001 using the DELU command in SHELXL (Sheldrick, 2008).

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 b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C24H21NO4SF(000) = 880
Mr = 419.48Dx = 1.313 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6715 reflections
a = 14.3655 (6) Åθ = 2.3–25.3°
b = 8.3432 (4) ŵ = 0.18 mm1
c = 18.6261 (8) ÅT = 295 K
β = 108.086 (2)°Block, colourless
V = 2122.12 (16) Å30.28 × 0.24 × 0.18 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer4712 independent reflections
Radiation source: fine-focus sealed tube3030 reflections with I > 2σ(I)
graphiteRint = 0.043
ω and [var phi] scansθmax = 27.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −18→18
Tmin = 0.951, Tmax = 0.968k = −9→10
23327 measured reflectionsl = −23→24

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0657P)2 + 0.817P] where P = (Fo2 + 2Fc2)/3
4712 reflections(Δ/σ)max < 0.001
273 parametersΔρmax = 0.26 e Å3
2 restraintsΔρmin = −0.35 e Å3

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

xyzUiso*/Ueq
C10.39968 (15)0.2073 (3)0.58199 (12)0.0515 (5)
C20.49717 (19)0.1911 (4)0.58978 (19)0.0807 (8)
H20.53610.28020.58970.097*
C30.5362 (2)0.0363 (4)0.5978 (2)0.0976 (10)
H30.60240.02160.60390.117*
C40.4786 (2)−0.0927 (4)0.59684 (17)0.0836 (8)
H40.5056−0.19490.60140.100*
C50.3827 (2)−0.0755 (3)0.58934 (16)0.0741 (7)
H50.3439−0.16520.58850.089*
C60.34286 (18)0.0747 (3)0.58297 (14)0.0645 (7)
H60.27720.08750.57930.077*
C70.15867 (14)0.3154 (3)0.49542 (11)0.0430 (5)
C80.11839 (14)0.2508 (2)0.42695 (11)0.0416 (5)
C90.18128 (14)0.2795 (3)0.38139 (11)0.0448 (5)
C100.17326 (19)0.2446 (3)0.30680 (13)0.0623 (6)
H100.11930.18940.27620.075*
C110.2471 (2)0.2937 (4)0.27933 (16)0.0780 (8)
H110.24290.27110.22950.094*
C120.3271 (2)0.3760 (4)0.32454 (18)0.0768 (8)
H120.37580.40840.30440.092*
C130.33684 (17)0.4113 (3)0.39800 (16)0.0624 (7)
H130.39130.46620.42830.075*
C140.26243 (14)0.3622 (2)0.42576 (12)0.0450 (5)
C150.11753 (18)0.3291 (4)0.55899 (14)0.0671 (7)
H15A0.05050.29420.54270.101*
H15B0.12070.43880.57520.101*
H15C0.15470.26330.60020.101*
C160.02422 (14)0.1601 (3)0.40188 (11)0.0441 (5)
H16−0.00230.15240.44430.053*
C170.03687 (14)−0.0071 (3)0.37520 (12)0.0462 (5)
C180.10644 (19)−0.1056 (3)0.42217 (16)0.0698 (7)
H180.1445−0.06810.46910.084*
C190.1201 (2)−0.2590 (4)0.4002 (2)0.0888 (10)
H190.1675−0.32400.43240.107*
C200.0652 (3)−0.3164 (4)0.3322 (2)0.0871 (9)
H200.0751−0.41990.31750.105*
C21−0.0047 (2)−0.2208 (4)0.28573 (17)0.0763 (8)
H21−0.0434−0.26000.23930.092*
C22−0.01860 (17)−0.0670 (3)0.30661 (13)0.0570 (6)
H22−0.0661−0.00280.27400.068*
C23−0.13810 (17)0.2461 (4)0.33675 (15)0.0638 (7)
C24−0.1970 (2)0.3458 (4)0.27301 (16)0.0905 (10)
H24A−0.26520.33530.26840.136*
H24B−0.18630.31070.22710.136*
H24C−0.17770.45590.28220.136*
N10.24997 (11)0.3880 (2)0.49744 (10)0.0460 (4)
O10.41254 (12)0.5105 (2)0.55926 (11)0.0776 (6)
O20.31180 (12)0.4240 (2)0.63643 (10)0.0722 (5)
O3−0.04306 (10)0.25213 (18)0.34207 (8)0.0521 (4)
O4−0.16788 (13)0.1681 (4)0.37807 (14)0.1077 (8)
S10.34717 (4)0.39792 (7)0.57453 (3)0.0550 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0450 (12)0.0497 (13)0.0509 (12)0.0019 (10)0.0020 (9)0.0002 (10)
C20.0482 (14)0.0716 (19)0.117 (2)0.0010 (13)0.0178 (15)0.0069 (16)
C30.0590 (17)0.089 (2)0.143 (3)0.0230 (13)0.0295 (18)0.018 (2)
C40.091 (2)0.0648 (18)0.093 (2)0.0246 (12)0.0245 (17)0.0178 (15)
C50.0770 (18)0.0534 (16)0.0851 (19)0.0061 (13)0.0152 (15)0.0120 (13)
C60.0546 (14)0.0528 (15)0.0786 (17)0.0003 (11)0.0098 (12)0.0062 (12)
C70.0348 (10)0.0437 (12)0.0481 (11)0.0009 (8)0.0095 (8)−0.0012 (9)
C80.0350 (10)0.0425 (11)0.0461 (11)0.0017 (8)0.0110 (8)0.0030 (8)
C90.0403 (11)0.0432 (12)0.0510 (12)0.0054 (9)0.0142 (9)0.0070 (9)
C100.0609 (14)0.0761 (18)0.0529 (13)0.0012 (12)0.0222 (11)0.0023 (12)
C110.0809 (19)0.101 (2)0.0631 (15)0.0118 (17)0.0387 (15)0.0146 (15)
C120.0630 (17)0.089 (2)0.093 (2)0.0123 (15)0.0453 (16)0.0327 (17)
C130.0435 (12)0.0586 (16)0.0878 (18)0.0013 (10)0.0243 (12)0.0209 (13)
C140.0359 (10)0.0392 (12)0.0596 (13)0.0060 (8)0.0146 (9)0.0117 (9)
C150.0537 (14)0.091 (2)0.0574 (14)−0.0115 (13)0.0185 (11)−0.0183 (13)
C160.0354 (10)0.0514 (13)0.0408 (10)−0.0007 (9)0.0050 (8)0.0027 (9)
C170.0374 (10)0.0471 (13)0.0515 (12)−0.0045 (9)0.0102 (9)0.0053 (9)
C180.0609 (15)0.0552 (16)0.0789 (17)0.0024 (12)0.0009 (13)0.0109 (13)
C190.082 (2)0.0535 (18)0.121 (3)0.0137 (15)0.0171 (19)0.0200 (17)
C200.103 (2)0.0510 (17)0.120 (3)0.0054 (17)0.052 (2)−0.0065 (17)
C210.089 (2)0.0676 (19)0.0777 (18)−0.0066 (16)0.0334 (16)−0.0204 (15)
C220.0571 (13)0.0588 (15)0.0527 (13)0.0017 (11)0.0135 (11)−0.0047 (11)
C230.0402 (12)0.0856 (19)0.0601 (14)0.0121 (12)0.0077 (11)−0.0171 (13)
C240.0653 (17)0.114 (3)0.0726 (17)0.0443 (17)−0.0071 (14)−0.0203 (16)
N10.0352 (9)0.0430 (10)0.0556 (10)−0.0032 (7)0.0082 (7)−0.0001 (8)
O10.0533 (10)0.0505 (11)0.1134 (15)−0.0194 (8)0.0033 (9)−0.0008 (10)
O20.0649 (10)0.0761 (12)0.0635 (9)0.0035 (9)0.0021 (7)−0.0289 (9)
O30.0376 (8)0.0569 (10)0.0549 (9)0.0070 (6)0.0041 (6)0.0029 (7)
O40.0438 (10)0.180 (3)0.1018 (16)0.0050 (13)0.0256 (11)0.0205 (17)
S10.0428 (3)0.0439 (3)0.0671 (4)−0.0055 (2)0.0009 (2)−0.0092 (3)

Geometric parameters (Å, °)

C1—C21.369 (3)C14—N11.418 (3)
C1—C61.378 (3)C15—H15A0.9600
C1—S11.747 (2)C15—H15B0.9600
C2—C31.398 (4)C15—H15C0.9600
C2—H20.9300C16—O31.448 (2)
C3—C41.354 (5)C16—C171.510 (3)
C3—H30.9300C16—H160.9800
C4—C51.349 (4)C17—C221.373 (3)
C4—H40.9300C17—C181.377 (3)
C5—C61.368 (4)C18—C191.376 (4)
C5—H50.9300C18—H180.9300
C6—H60.9300C19—C201.354 (5)
C7—C81.339 (3)C19—H190.9300
C7—N11.434 (3)C20—C211.362 (4)
C7—C151.483 (3)C20—H200.9300
C8—C91.438 (3)C21—C221.373 (4)
C8—C161.493 (3)C21—H210.9300
C9—C141.386 (3)C22—H220.9300
C9—C101.389 (3)C23—O41.184 (3)
C10—C111.375 (4)C23—O31.339 (3)
C10—H100.9300C23—C241.481 (4)
C11—C121.379 (4)C24—H24A0.9600
C11—H110.9300C24—H24B0.9600
C12—C131.364 (4)C24—H24C0.9600
C12—H120.9300N1—S11.6653 (17)
C13—C141.386 (3)O1—S11.4181 (18)
C13—H130.9300O2—S11.4137 (19)
C2—C1—C6120.7 (2)H15A—C15—H15C109.5
C2—C1—S1120.0 (2)H15B—C15—H15C109.5
C6—C1—S1119.25 (18)O3—C16—C8107.17 (17)
C1—C2—C3117.7 (3)O3—C16—C17110.88 (16)
C1—C2—H2121.1C8—C16—C17112.41 (17)
C3—C2—H2121.1O3—C16—H16108.8
C4—C3—C2120.7 (3)C8—C16—H16108.8
C4—C3—H3119.7C17—C16—H16108.8
C2—C3—H3119.7C22—C17—C18118.1 (2)
C5—C4—C3121.1 (3)C22—C17—C16123.24 (19)
C5—C4—H4119.4C18—C17—C16118.7 (2)
C3—C4—H4119.4C19—C18—C17120.5 (3)
C4—C5—C6119.5 (3)C19—C18—H18119.7
C4—C5—H5120.2C17—C18—H18119.7
C6—C5—H5120.2C20—C19—C18120.8 (3)
C5—C6—C1120.2 (2)C20—C19—H19119.6
C5—C6—H6119.9C18—C19—H19119.6
C1—C6—H6119.9C19—C20—C21119.2 (3)
C8—C7—N1108.42 (17)C19—C20—H20120.4
C8—C7—C15129.05 (19)C21—C20—H20120.4
N1—C7—C15122.29 (18)C20—C21—C22120.7 (3)
C7—C8—C9109.27 (18)C20—C21—H21119.6
C7—C8—C16125.70 (18)C22—C21—H21119.6
C9—C8—C16125.02 (18)C21—C22—C17120.7 (2)
C14—C9—C10119.6 (2)C21—C22—H22119.6
C14—C9—C8107.29 (18)C17—C22—H22119.6
C10—C9—C8133.1 (2)O4—C23—O3122.6 (2)
C11—C10—C9118.4 (3)O4—C23—C24126.7 (3)
C11—C10—H10120.8O3—C23—C24110.7 (3)
C9—C10—H10120.8C23—C24—H24A109.5
C10—C11—C12121.0 (3)C23—C24—H24B109.5
C10—C11—H11119.5H24A—C24—H24B109.5
C12—C11—H11119.5C23—C24—H24C109.5
C13—C12—C11121.8 (2)H24A—C24—H24C109.5
C13—C12—H12119.1H24B—C24—H24C109.5
C11—C12—H12119.1C14—N1—C7107.05 (16)
C12—C13—C14117.4 (2)C14—N1—S1120.16 (13)
C12—C13—H13121.3C7—N1—S1123.97 (14)
C14—C13—H13121.3C23—O3—C16117.29 (19)
C9—C14—C13121.9 (2)O2—S1—O1119.30 (12)
C9—C14—N1107.96 (17)O2—S1—N1107.07 (10)
C13—C14—N1130.1 (2)O1—S1—N1106.87 (10)
C7—C15—H15A109.5O2—S1—C1109.33 (11)
C7—C15—H15B109.5O1—S1—C1108.81 (11)
H15A—C15—H15B109.5N1—S1—C1104.41 (9)
C7—C15—H15C109.5
C6—C1—C2—C30.7 (4)C8—C16—C17—C1853.1 (3)
S1—C1—C2—C3178.1 (2)C22—C17—C18—C190.6 (4)
C1—C2—C3—C40.8 (5)C16—C17—C18—C19179.7 (2)
C2—C3—C4—C5−1.1 (5)C17—C18—C19—C20−0.3 (5)
C3—C4—C5—C6−0.3 (5)C18—C19—C20—C21−0.5 (5)
C4—C5—C6—C11.9 (4)C19—C20—C21—C221.1 (5)
C2—C1—C6—C5−2.1 (4)C20—C21—C22—C17−0.8 (4)
S1—C1—C6—C5−179.5 (2)C18—C17—C22—C21−0.1 (3)
N1—C7—C8—C9−0.4 (2)C16—C17—C22—C21−179.1 (2)
C15—C7—C8—C9174.1 (2)C9—C14—N1—C70.9 (2)
N1—C7—C8—C16178.36 (18)C13—C14—N1—C7178.2 (2)
C15—C7—C8—C16−7.1 (4)C9—C14—N1—S1149.55 (15)
C7—C8—C9—C140.9 (2)C13—C14—N1—S1−33.1 (3)
C16—C8—C9—C14−177.81 (19)C8—C7—N1—C14−0.3 (2)
C7—C8—C9—C10−177.2 (2)C15—C7—N1—C14−175.3 (2)
C16—C8—C9—C104.0 (4)C8—C7—N1—S1−147.47 (16)
C14—C9—C10—C110.1 (4)C15—C7—N1—S137.6 (3)
C8—C9—C10—C11178.1 (2)O4—C23—O3—C16−0.8 (4)
C9—C10—C11—C12−0.2 (4)C24—C23—O3—C16−179.9 (2)
C10—C11—C12—C130.4 (5)C8—C16—O3—C23−146.89 (19)
C11—C12—C13—C14−0.5 (4)C17—C16—O3—C2390.1 (2)
C10—C9—C14—C13−0.3 (3)C14—N1—S1—O2−179.98 (16)
C8—C9—C14—C13−178.72 (19)C7—N1—S1—O2−36.81 (19)
C10—C9—C14—N1177.35 (19)C14—N1—S1—O151.11 (18)
C8—C9—C14—N1−1.1 (2)C7—N1—S1—O1−165.73 (17)
C12—C13—C14—C90.4 (3)C14—N1—S1—C1−64.10 (17)
C12—C13—C14—N1−176.6 (2)C7—N1—S1—C179.06 (18)
C7—C8—C16—O3115.6 (2)C2—C1—S1—O2−117.5 (2)
C9—C8—C16—O3−65.9 (2)C6—C1—S1—O259.9 (2)
C7—C8—C16—C17−122.4 (2)C2—C1—S1—O114.3 (3)
C9—C8—C16—C1756.2 (3)C6—C1—S1—O1−168.25 (19)
O3—C16—C17—C22−7.9 (3)C2—C1—S1—N1128.2 (2)
C8—C16—C17—C22−127.9 (2)C6—C1—S1—N1−54.4 (2)
O3—C16—C17—C18173.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13···O10.932.392.977 (4)121
C24—H24B···O2i0.962.583.429 (4)147
C15—H15A···Cg1ii0.962.973.590 (3)124

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2478).

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