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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o954.
Published online 2010 March 27. doi:  10.1107/S1600536810010044
PMCID: PMC2983998

1-(Phenyl­sulfon­yl)benzo[1,2:2′,3′]thieno[5′,4′-b]carbazole

Abstract

In the title compound, C24H15NO2S2, the ring system composed of the five fused rings is almost planar (r.m.s. deviation for all non-H atoms = 0.056 Å). The dihedral angle between the fused ring system and the phenyl ring is 83.4 (9)°. The crystal packing is stabilized by C—H(...)π and π–π inter­actions between parallel ring systems [centroid–centroid distances = 3.526 (3), 3.877 (3) and 3.712 (3) Å].

Related literature

For related structures, see: Murugavel et al. (2009 [triangle]); Chakkaravarthi et al. (2008 [triangle]); Ravishankar et al. (2005 [triangle]).

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Object name is e-66-0o954-scheme1.jpg

Experimental

Crystal data

  • C24H15NO2S2
  • M r = 413.49
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o954-efi1.jpg
  • a = 7.463 (5) Å
  • b = 10.462 (5) Å
  • c = 12.335 (5) Å
  • α = 80.438 (5)°
  • β = 89.433 (5)°
  • γ = 81.876 (5)°
  • V = 940.1 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.31 mm−1
  • T = 293 K
  • 0.25 × 0.22 × 0.19 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.981, T max = 0.985
  • 24843 measured reflections
  • 6428 independent reflections
  • 4863 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.192
  • S = 1.01
  • 6428 reflections
  • 262 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.98 e Å−3
  • Δρmin = −0.62 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: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010044/bt5204sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010044/bt5204Isup2.hkl

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

Acknowledgments

ST and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

Carbazole and its derivatives have become quite attractive compounds owing to their applications in pharmacy and molecular electronics.

In order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

The ring system composed of the five rings is almost planar (r.m.s. deviation for all non-H atoms 0.056Å). The crystal packing is stabilized by C–H..O and C–H···π (Table. 1) hydrogen bonds. In addition, there are π–π interactions between the extended ring system with a mean distance between the ring planes of 3.7Å.

Experimental

To a solution of diethyl-2-((2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl) methylene)malonate (0.3 g 0.57 mmol) in dry 1,2-DCE (10 ml), InBr3 (0.02 g 0.06 mmol) and benzo[b]thiophene (0.09 g, 0.67 mmol) were added. The reaction mixture was stirred at room temperature for 4 h and then refluxed for 1 h under N2 atmosphere. It was then poured over ice-water (30 ml) containing 1 ml of Conc.HCl, extracted with chloroform (2 X 10 ml) and dried (Na2SO4). The removal of solvent followed by flash column chromatographic purification (silica gel, 230-420 mesh, n-hexane/ethyl acetate 99:1) afforded the product as a colorless solid. The product was recrystallization from CDCl3

Refinement

All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with C—H distances fixed in the range 0.93–0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl H 1.2Ueq(C) for other H atoms.

Figures

Fig. 1.
The structure of showing the atom-numbering scheme and intramolecular hydrogen bond. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
The molecular packing viewed down the a axis.

Crystal data

C24H15NO2S2Z = 2
Mr = 413.49F(000) = 428
Triclinic, P1Dx = 1.461 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.463 (5) ÅCell parameters from 6428 reflections
b = 10.462 (5) Åθ = 1.7–32.2°
c = 12.335 (5) ŵ = 0.31 mm1
α = 80.438 (5)°T = 293 K
β = 89.433 (5)°Block, white crystalline
γ = 81.876 (5)°0.25 × 0.22 × 0.19 mm
V = 940.1 (9) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer6428 independent reflections
Radiation source: fine-focus sealed tube4863 reflections with I > 2σ(I)
graphiteRint = 0.024
ω and [var phi] scansθmax = 32.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.981, Tmax = 0.985k = −15→15
24843 measured reflectionsl = −18→17

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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.1079P)2 + 0.4678P] where P = (Fo2 + 2Fc2)/3
6428 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.98 e Å3
3 restraintsΔρmin = −0.61 e Å3

Special details

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

xyzUiso*/Ueq
C10.8004 (3)0.5479 (2)0.66419 (19)0.0477 (5)
H10.85370.46280.69100.057*
C20.7893 (3)0.5939 (3)0.5527 (2)0.0538 (5)
H20.83550.53910.50380.065*
C30.7106 (3)0.7203 (3)0.51279 (18)0.0517 (5)
H30.70500.74910.43720.062*
C40.6398 (3)0.8051 (2)0.58229 (17)0.0456 (4)
H40.58780.89040.55500.055*
C50.6495 (3)0.75792 (19)0.69390 (15)0.0367 (4)
C60.7303 (3)0.63112 (18)0.73581 (16)0.0368 (4)
C70.7156 (2)0.61248 (17)0.85389 (15)0.0347 (3)
C80.6261 (2)0.72886 (17)0.88294 (15)0.0344 (3)
C90.5880 (3)0.74249 (19)0.99044 (16)0.0394 (4)
H90.52910.82021.00890.047*
C100.6430 (3)0.63321 (19)1.06946 (15)0.0380 (4)
C110.7341 (2)0.51533 (18)1.04347 (15)0.0360 (4)
C120.7710 (3)0.50503 (19)0.93443 (16)0.0388 (4)
H120.83140.42790.91580.047*
C130.7743 (3)0.4149 (2)1.13958 (16)0.0402 (4)
C140.8661 (3)0.2850 (2)1.1441 (2)0.0502 (5)
H140.91230.25411.08150.060*
C150.8825 (4)0.2076 (2)1.2471 (2)0.0564 (5)
H150.93930.12151.25540.068*
C160.8114 (3)0.2611 (3)1.34032 (18)0.0531 (5)
H160.82800.20791.40880.064*
C170.7254 (4)0.3785 (3)1.3365 (2)0.0593 (6)
H170.67680.40771.39920.071*
C180.7093 (3)0.4578 (2)1.23556 (18)0.0482 (5)
C190.6988 (3)1.05404 (18)0.76966 (16)0.0378 (4)
C200.7881 (3)1.0581 (2)0.86625 (19)0.0478 (5)
H200.74591.02080.93360.057*
C210.9420 (3)1.1189 (3)0.8608 (2)0.0579 (6)
H211.00361.12280.92500.070*
C221.0040 (4)1.1735 (3)0.7611 (3)0.0606 (6)
H221.10821.21330.75810.073*
C230.9128 (4)1.1697 (3)0.6658 (2)0.0648 (7)
H230.95491.20780.59870.078*
C240.7592 (3)1.1098 (2)0.6689 (2)0.0517 (5)
H240.69741.10700.60440.062*
N10.5814 (2)0.81927 (16)0.78385 (13)0.0385 (3)
O10.4119 (2)1.01545 (15)0.67159 (13)0.0470 (3)
O20.4131 (2)0.99247 (15)0.87383 (13)0.0461 (3)
S10.50484 (6)0.97634 (4)0.77433 (4)0.03684 (13)
S20.60075 (9)0.62317 (6)1.20851 (5)0.05295 (17)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0510 (11)0.0457 (11)0.0460 (11)0.0000 (9)0.0036 (9)−0.0127 (9)
C20.0555 (13)0.0620 (14)0.0468 (12)−0.0036 (10)0.0082 (10)−0.0223 (10)
C30.0546 (12)0.0650 (14)0.0358 (10)−0.0087 (10)0.0050 (9)−0.0093 (9)
C40.0495 (11)0.0495 (11)0.0351 (9)−0.0042 (9)−0.0001 (8)−0.0014 (8)
C50.0378 (9)0.0393 (9)0.0331 (8)−0.0059 (7)0.0009 (7)−0.0055 (7)
C60.0359 (8)0.0373 (9)0.0375 (9)−0.0053 (7)0.0006 (7)−0.0064 (7)
C70.0342 (8)0.0341 (8)0.0356 (8)−0.0046 (6)0.0002 (6)−0.0053 (6)
C80.0366 (8)0.0312 (8)0.0346 (8)−0.0055 (6)0.0005 (6)−0.0026 (6)
C90.0485 (10)0.0346 (8)0.0348 (9)−0.0041 (7)0.0029 (7)−0.0070 (7)
C100.0439 (10)0.0366 (9)0.0348 (8)−0.0096 (7)0.0007 (7)−0.0067 (7)
C110.0358 (8)0.0364 (8)0.0351 (8)−0.0065 (7)−0.0028 (7)−0.0027 (6)
C120.0414 (9)0.0351 (8)0.0389 (9)−0.0019 (7)0.0001 (7)−0.0065 (7)
C130.0391 (9)0.0427 (8)0.0385 (9)−0.0114 (7)−0.0037 (7)−0.0006 (7)
C140.0469 (11)0.0470 (9)0.0523 (12)−0.0071 (8)−0.0063 (9)0.0053 (9)
C150.0573 (13)0.0452 (11)0.0607 (12)−0.0046 (10)−0.0072 (10)0.0071 (9)
C160.0505 (12)0.0673 (12)0.0383 (9)−0.0205 (9)−0.0106 (8)0.0116 (8)
C170.0689 (15)0.0661 (12)0.0443 (11)−0.0252 (10)−0.0056 (11)−0.0001 (10)
C180.0519 (12)0.0587 (13)0.0379 (10)−0.0244 (10)−0.0010 (8)−0.0053 (9)
C190.0377 (9)0.0340 (8)0.0402 (9)−0.0014 (7)0.0009 (7)−0.0051 (7)
C200.0466 (11)0.0518 (12)0.0438 (11)−0.0014 (9)−0.0003 (8)−0.0093 (9)
C210.0500 (13)0.0619 (14)0.0647 (15)−0.0057 (10)−0.0092 (11)−0.0199 (12)
C220.0475 (12)0.0555 (14)0.0813 (18)−0.0152 (10)0.0011 (12)−0.0116 (12)
C230.0622 (15)0.0656 (16)0.0658 (16)−0.0245 (13)0.0082 (12)0.0045 (12)
C240.0561 (13)0.0546 (12)0.0434 (11)−0.0166 (10)0.0006 (9)0.0021 (9)
N10.0475 (9)0.0335 (7)0.0325 (7)−0.0013 (6)0.0013 (6)−0.0033 (6)
O10.0434 (8)0.0467 (8)0.0464 (8)0.0002 (6)−0.0085 (6)0.0007 (6)
O20.0452 (8)0.0437 (8)0.0460 (8)0.0023 (6)0.0109 (6)−0.0060 (6)
S10.0362 (2)0.0344 (2)0.0371 (2)−0.00038 (16)0.00092 (17)−0.00168 (16)
S20.0709 (4)0.0497 (3)0.0405 (3)−0.0133 (3)0.0044 (2)−0.0102 (2)

Geometric parameters (Å, °)

C1—C21.379 (3)C14—C151.386 (3)
C1—C61.389 (3)C14—H140.9300
C1—H10.9300C15—C161.426 (4)
C2—C31.381 (4)C15—H150.9300
C2—H20.9300C16—C171.297 (4)
C3—C41.383 (3)C16—H160.9300
C3—H30.9300C17—C181.372 (3)
C4—C51.382 (3)C17—H170.9300
C4—H40.9300C18—S21.783 (3)
C5—C61.394 (3)C19—C201.381 (3)
C5—N11.427 (2)C19—C241.382 (3)
C6—C71.442 (3)C19—S11.753 (2)
C7—C121.388 (3)C20—C211.385 (4)
C7—C81.403 (3)C20—H200.9300
C8—C91.380 (3)C21—C221.371 (4)
C8—N11.426 (2)C21—H210.9300
C9—C101.389 (3)C22—C231.373 (4)
C9—H90.9300C22—H220.9300
C10—C111.406 (3)C23—C241.380 (4)
C10—S21.729 (2)C23—H230.9300
C11—C121.389 (3)C24—H240.9300
C11—C131.450 (3)N1—S11.6469 (18)
C12—H120.9300O1—S11.4212 (16)
C13—C181.393 (3)O2—S11.4223 (16)
C13—C141.425 (3)
C2—C1—C6118.7 (2)C13—C14—H14122.0
C2—C1—H1120.6C14—C15—C16119.5 (2)
C6—C1—H1120.6C14—C15—H15120.3
C1—C2—C3120.7 (2)C16—C15—H15120.3
C1—C2—H2119.6C17—C16—C15124.7 (2)
C3—C2—H2119.6C17—C16—H16117.6
C2—C3—C4121.7 (2)C15—C16—H16117.6
C2—C3—H3119.1C16—C17—C18116.9 (3)
C4—C3—H3119.1C16—C17—H17121.5
C5—C4—C3117.2 (2)C18—C17—H17121.5
C5—C4—H4121.4C17—C18—C13122.7 (3)
C3—C4—H4121.4C17—C18—S2125.7 (2)
C4—C5—C6121.90 (19)C13—C18—S2111.53 (16)
C4—C5—N1129.92 (19)C20—C19—C24121.4 (2)
C6—C5—N1108.16 (16)C20—C19—S1119.55 (16)
C1—C6—C5119.68 (19)C24—C19—S1119.07 (17)
C1—C6—C7132.31 (19)C19—C20—C21118.7 (2)
C5—C6—C7107.97 (16)C19—C20—H20120.7
C12—C7—C8120.30 (17)C21—C20—H20120.7
C12—C7—C6131.54 (17)C22—C21—C20120.4 (2)
C8—C7—C6108.15 (16)C22—C21—H21119.8
C9—C8—C7122.62 (17)C20—C21—H21119.8
C9—C8—N1129.72 (17)C21—C22—C23120.3 (2)
C7—C8—N1107.63 (16)C21—C22—H22119.9
C8—C9—C10116.03 (18)C23—C22—H22119.9
C8—C9—H9122.0C22—C23—C24120.5 (3)
C10—C9—H9122.0C22—C23—H23119.7
C9—C10—C11122.92 (18)C24—C23—H23119.7
C9—C10—S2124.73 (16)C23—C24—C19118.7 (2)
C11—C10—S2112.31 (14)C23—C24—H24120.6
C12—C11—C10119.59 (17)C19—C24—H24120.6
C12—C11—C13127.69 (18)C8—N1—C5108.07 (15)
C10—C11—C13112.69 (18)C8—N1—S1126.27 (13)
C7—C12—C11118.53 (17)C5—N1—S1124.47 (13)
C7—C12—H12120.7O1—S1—O2120.28 (10)
C11—C12—H12120.7O1—S1—N1106.82 (9)
C18—C13—C14120.1 (2)O2—S1—N1106.80 (9)
C18—C13—C11112.01 (19)O1—S1—C19108.43 (10)
C14—C13—C11127.9 (2)O2—S1—C19108.38 (10)
C15—C14—C13116.0 (2)N1—S1—C19105.12 (10)
C15—C14—H14122.0C10—S2—C1891.45 (10)
C6—C1—C2—C30.1 (4)C15—C16—C17—C18−2.9 (4)
C1—C2—C3—C4−0.1 (4)C16—C17—C18—C132.7 (4)
C2—C3—C4—C5−0.6 (4)C16—C17—C18—S2−179.09 (18)
C3—C4—C5—C61.3 (3)C14—C13—C18—C17−1.7 (3)
C3—C4—C5—N1−176.6 (2)C11—C13—C18—C17177.6 (2)
C2—C1—C6—C50.5 (3)C14—C13—C18—S2179.82 (16)
C2—C1—C6—C7177.8 (2)C11—C13—C18—S2−0.8 (2)
C4—C5—C6—C1−1.3 (3)C24—C19—C20—C21−0.4 (3)
N1—C5—C6—C1177.01 (18)S1—C19—C20—C21179.44 (18)
C4—C5—C6—C7−179.18 (18)C19—C20—C21—C22−0.2 (4)
N1—C5—C6—C7−0.9 (2)C20—C21—C22—C230.7 (4)
C1—C6—C7—C121.5 (4)C21—C22—C23—C24−0.7 (5)
C5—C6—C7—C12179.1 (2)C22—C23—C24—C190.1 (4)
C1—C6—C7—C8−177.7 (2)C20—C19—C24—C230.4 (4)
C5—C6—C7—C8−0.2 (2)S1—C19—C24—C23−179.4 (2)
C12—C7—C8—C9−0.4 (3)C9—C8—N1—C5−179.31 (19)
C6—C7—C8—C9178.97 (17)C7—C8—N1—C5−1.7 (2)
C12—C7—C8—N1−178.20 (17)C9—C8—N1—S112.8 (3)
C6—C7—C8—N11.1 (2)C7—C8—N1—S1−169.59 (14)
C7—C8—C9—C10−0.3 (3)C4—C5—N1—C8179.7 (2)
N1—C8—C9—C10176.99 (18)C6—C5—N1—C81.6 (2)
C8—C9—C10—C110.8 (3)C4—C5—N1—S1−12.1 (3)
C8—C9—C10—S2−176.55 (14)C6—C5—N1—S1169.78 (14)
C9—C10—C11—C12−0.6 (3)C8—N1—S1—O1−156.86 (17)
S2—C10—C11—C12177.07 (15)C5—N1—S1—O137.10 (18)
C9—C10—C11—C13−178.95 (18)C8—N1—S1—O2−27.0 (2)
S2—C10—C11—C13−1.3 (2)C5—N1—S1—O2167.01 (16)
C8—C7—C12—C110.6 (3)C8—N1—S1—C1988.06 (18)
C6—C7—C12—C11−178.54 (19)C5—N1—S1—C19−77.97 (17)
C10—C11—C12—C7−0.2 (3)C20—C19—S1—O1164.32 (16)
C13—C11—C12—C7177.95 (18)C24—C19—S1—O1−15.8 (2)
C12—C11—C13—C18−176.85 (19)C20—C19—S1—O232.19 (19)
C10—C11—C13—C181.4 (2)C24—C19—S1—O2−147.95 (18)
C12—C11—C13—C142.4 (3)C20—C19—S1—N1−81.72 (18)
C10—C11—C13—C14−179.34 (19)C24—C19—S1—N198.14 (19)
C18—C13—C14—C150.8 (3)C9—C10—S2—C18178.30 (19)
C11—C13—C14—C15−178.4 (2)C11—C10—S2—C180.71 (15)
C13—C14—C15—C16−1.0 (3)C17—C18—S2—C10−178.3 (2)
C14—C15—C16—C172.2 (4)C13—C18—S2—C100.08 (16)

Hydrogen-bond geometry (Å, °)

Cg6 is the centeroid of the C19–C24 ring.
D—H···AD—HH···AD···AD—H···A
C15—H15···Cg6i0.932.783.685 (4)166

Symmetry codes: (i) −x+2, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5204).

References

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