PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2895.
Published online 2010 October 23. doi:  10.1107/S1600536810042261
PMCID: PMC3009149

(Phen­yl)(1-phenyl­sulfonyl-1H-indol-3-yl)methanone

Abstract

In the title compound, C21H15NO3S, the sulfonyl-bound phenyl ring forms a dihedral angle of 86.28 (5)° with the indole ring system. The mol­ecular structure is stabilized by intra­molecular C—H(...)O hydrogen bonds. The crystal packing is stabilized by weak inter­molecular C—H(...)O and C—H(...)π inter­actions.

Related literature

For the structures of closely related compounds, see: Chakkaravarthi et al. (2007 [triangle], 2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2895-scheme1.jpg

Experimental

Crystal data

  • C21H15NO3S
  • M r = 361.40
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2895-efi1.jpg
  • a = 7.567 (1) Å
  • b = 10.571 (2) Å
  • c = 12.083 (3) Å
  • α = 66.302 (2)°
  • β = 80.740 (1)°
  • γ = 78.403 (1)°
  • V = 863.5 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 295 K
  • 0.24 × 0.22 × 0.20 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.952, T max = 0.960
  • 15638 measured reflections
  • 4276 independent reflections
  • 3187 reflections with I > 2σ(I)
  • R int = 0.026
  • Standard reflections: 0

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.109
  • S = 1.01
  • 4276 reflections
  • 235 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.29 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 I, global. DOI: 10.1107/S1600536810042261/bt5379sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042261/bt5379Isup2.hkl

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

Acknowledgments

The authors wish to acknowledge DV University of Madras for the data collection.

supplementary crystallographic information

Comment

The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported values of similar structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008). The phenyl rings C1—C6 and C16—C21 form the dihedral angles of 86.28 (5)° and 51.91 (5)°, respectively with the indole ring system. The mean planes of the two phenyl rings are inclined at an angle of 42.16 (6)°.

The sum of the bond angles around N1 [358.53°] indicates that N1 atom is sp2 hybridized. The molecular structure is stabilized by intra molecular C—H···O hydrogen bonds and the crystal packing is stabilized by weak intermolecular C—H···O and C—H···π [C4—H4···Cg1 (1 - x, -y, -z) distance of 3.774 (3)Å (Cg1 is the centroid of the ring defined by the atoms C16—C21)] interactions.

Experimental

To a solution of 1-phenylsulfonyl-(1H-indol-3-yl)(phenyl)methanol (1 g, 2.75 mmol) in dry 1,2-Dichloroethane (30 ml), manganese dioxide (6 g. 68.96 mmol) was added then stirred at room temperature for 4 h and then refluxed for 3 h. Then the resulting solution was passed through celite pad and washed with DCM (2 x 30 ml). Removal of solvent followed by crystallization from methanol afforded the compound as a colourless crystal.

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. The components of the anisotropic displacement parameters in direction of the bond of C3and C4; C18 and C19 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.
Fig. 2.
The packing of (I), viewed down the a axis. H-bonds are shown as dashed lines; H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C21H15NO3SZ = 2
Mr = 361.40F(000) = 376
Triclinic, P1Dx = 1.390 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.567 (1) ÅCell parameters from 6196 reflections
b = 10.571 (2) Åθ = 2.2–27.1°
c = 12.083 (3) ŵ = 0.21 mm1
α = 66.302 (2)°T = 295 K
β = 80.740 (1)°Block, colourless
γ = 78.403 (1)°0.24 × 0.22 × 0.20 mm
V = 863.5 (3) Å3

Data collection

Bruker Kappa APEXII diffractometer4276 independent reflections
Radiation source: fine-focus sealed tube3187 reflections with I > 2σ(I)
graphiteRint = 0.026
ω and [var phi] scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.952, Tmax = 0.960k = −14→13
15638 measured reflectionsl = −16→16

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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0543P)2 + 0.1447P] where P = (Fo2 + 2Fc2)/3
4276 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.21 e Å3
2 restraintsΔρmin = −0.29 e Å3

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

xyzUiso*/Ueq
C10.7233 (2)0.05722 (16)0.20701 (13)0.0494 (4)
C20.6154 (3)0.0869 (2)0.29978 (15)0.0648 (5)
H20.65230.13880.33600.078*
C30.4508 (3)0.0376 (2)0.33759 (18)0.0791 (5)
H30.37590.05670.39970.095*
C40.3975 (3)−0.0394 (2)0.2838 (2)0.0806 (6)
H40.2866−0.07180.30970.097*
C50.5061 (3)−0.0687 (2)0.1928 (2)0.0757 (5)
H50.4690−0.12150.15750.091*
C60.6701 (2)−0.02074 (19)0.15289 (17)0.0615 (4)
H60.7440−0.04030.09060.074*
C140.80636 (19)0.40437 (16)0.04797 (13)0.0448 (3)
C130.7914 (2)0.44779 (18)0.14366 (15)0.0547 (4)
H130.83050.38730.21880.066*
C120.7164 (2)0.5838 (2)0.12251 (18)0.0641 (5)
H120.70180.61570.18530.077*
C110.6617 (3)0.6751 (2)0.00966 (19)0.0681 (5)
H110.61300.7671−0.00190.082*
C100.6778 (2)0.63262 (18)−0.08489 (17)0.0609 (4)
H100.64120.6948−0.16030.073*
C90.75050 (19)0.49375 (16)−0.06607 (14)0.0472 (3)
C80.7882 (2)0.41551 (16)−0.14359 (13)0.0474 (3)
C70.86292 (19)0.28383 (16)−0.07641 (12)0.0469 (3)
H70.89820.2113−0.10400.056*
C150.7413 (2)0.46868 (18)−0.26928 (14)0.0546 (4)
C160.8200 (2)0.39033 (18)−0.34881 (13)0.0553 (4)
C210.9990 (3)0.32957 (19)−0.35204 (14)0.0634 (5)
H211.07370.3291−0.29780.076*
C201.0679 (3)0.2692 (2)−0.43577 (17)0.0807 (6)
H201.18930.2301−0.43910.097*
C190.9549 (4)0.2676 (2)−0.51451 (18)0.0891 (6)
H191.00000.2259−0.57000.107*
C180.7771 (4)0.3274 (3)−0.51087 (19)0.0900 (6)
H180.70170.3266−0.56420.108*
C170.7103 (3)0.3879 (2)−0.42929 (16)0.0742 (5)
H170.58940.4283−0.42750.089*
N10.87874 (17)0.27365 (13)0.04012 (10)0.0461 (3)
O10.98538 (16)0.15404 (13)0.24616 (10)0.0602 (3)
O21.04747 (14)0.03484 (12)0.10209 (10)0.0543 (3)
O30.63449 (19)0.57703 (15)−0.30880 (11)0.0789 (4)
S10.92933 (5)0.12195 (4)0.15505 (3)0.04628 (13)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0554 (8)0.0428 (8)0.0381 (7)0.0021 (7)−0.0076 (6)−0.0064 (6)
C20.0723 (11)0.0626 (11)0.0470 (9)−0.0010 (9)0.0007 (8)−0.0146 (8)
C30.0696 (12)0.0795 (14)0.0578 (11)0.0037 (10)0.0110 (9)−0.0082 (9)
C40.0579 (10)0.0687 (13)0.0827 (14)−0.0089 (9)−0.0036 (10)0.0032 (9)
C50.0669 (11)0.0698 (13)0.0848 (14)−0.0156 (10)−0.0104 (10)−0.0201 (11)
C60.0619 (10)0.0604 (11)0.0593 (10)−0.0069 (8)−0.0060 (8)−0.0209 (8)
C140.0447 (7)0.0433 (8)0.0444 (7)−0.0093 (6)−0.0023 (6)−0.0140 (6)
C130.0606 (9)0.0553 (10)0.0513 (9)−0.0105 (8)−0.0034 (7)−0.0234 (8)
C120.0666 (10)0.0632 (12)0.0739 (12)−0.0113 (9)−0.0011 (9)−0.0391 (10)
C110.0712 (11)0.0486 (10)0.0844 (13)−0.0044 (8)−0.0049 (10)−0.0280 (10)
C100.0611 (10)0.0473 (9)0.0632 (10)−0.0049 (8)−0.0074 (8)−0.0107 (8)
C90.0440 (7)0.0465 (8)0.0456 (8)−0.0096 (6)−0.0016 (6)−0.0115 (6)
C80.0483 (8)0.0496 (9)0.0386 (7)−0.0083 (6)−0.0041 (6)−0.0105 (6)
C70.0535 (8)0.0499 (9)0.0359 (7)−0.0072 (7)−0.0052 (6)−0.0149 (6)
C150.0546 (8)0.0571 (10)0.0403 (8)−0.0080 (7)−0.0082 (7)−0.0053 (7)
C160.0677 (10)0.0550 (10)0.0337 (7)−0.0120 (8)−0.0094 (7)−0.0041 (7)
C210.0728 (11)0.0691 (12)0.0399 (8)−0.0044 (9)−0.0087 (8)−0.0138 (8)
C200.1019 (15)0.0786 (14)0.0471 (10)0.0032 (12)0.0000 (10)−0.0194 (9)
C190.1479 (17)0.0736 (14)0.0441 (9)−0.0172 (13)−0.0036 (12)−0.0223 (10)
C180.1306 (15)0.0951 (17)0.0512 (10)−0.0334 (13)−0.0220 (12)−0.0222 (11)
C170.0873 (13)0.0821 (14)0.0465 (9)−0.0182 (11)−0.0203 (9)−0.0097 (9)
N10.0566 (7)0.0434 (7)0.0357 (6)−0.0037 (6)−0.0071 (5)−0.0132 (5)
O10.0728 (7)0.0643 (7)0.0457 (6)−0.0020 (6)−0.0197 (5)−0.0220 (5)
O20.0551 (6)0.0540 (7)0.0498 (6)0.0039 (5)−0.0072 (5)−0.0205 (5)
O30.0817 (9)0.0791 (9)0.0539 (7)0.0174 (7)−0.0184 (6)−0.0119 (7)
S10.0526 (2)0.0470 (2)0.03579 (19)0.00011 (16)−0.00991 (15)−0.01356 (15)

Geometric parameters (Å, °)

C1—C21.381 (2)C10—H100.9300
C1—C61.386 (2)C9—C81.444 (2)
C1—S11.7498 (17)C8—C71.356 (2)
C2—C31.384 (3)C8—C151.468 (2)
C2—H20.9300C7—N11.3913 (18)
C3—C41.375 (3)C7—H70.9300
C3—H30.9300C15—O31.227 (2)
C4—C51.364 (3)C15—C161.490 (2)
C4—H40.9300C16—C211.379 (2)
C5—C61.376 (3)C16—C171.387 (2)
C5—H50.9300C21—C201.385 (3)
C6—H60.9300C21—H210.9300
C14—C131.387 (2)C20—C191.385 (3)
C14—C91.397 (2)C20—H200.9300
C14—N11.4152 (19)C19—C181.369 (3)
C13—C121.370 (2)C19—H190.9300
C13—H130.9300C18—C171.361 (3)
C12—C111.388 (3)C18—H180.9300
C12—H120.9300C17—H170.9300
C11—C101.366 (3)N1—S11.6677 (12)
C11—H110.9300O1—S11.4195 (11)
C10—C91.399 (2)O2—S11.4195 (11)
C2—C1—C6121.26 (17)C7—C8—C9107.38 (13)
C2—C1—S1119.33 (14)C7—C8—C15127.21 (15)
C6—C1—S1119.39 (12)C9—C8—C15125.29 (15)
C1—C2—C3118.46 (19)C8—C7—N1109.68 (13)
C1—C2—H2120.8C8—C7—H7125.2
C3—C2—H2120.8N1—C7—H7125.2
C4—C3—C2120.39 (18)O3—C15—C8119.99 (16)
C4—C3—H3119.8O3—C15—C16119.61 (14)
C2—C3—H3119.8C8—C15—C16120.39 (14)
C5—C4—C3120.5 (2)C21—C16—C17118.93 (18)
C5—C4—H4119.7C21—C16—C15123.05 (15)
C3—C4—H4119.7C17—C16—C15117.84 (17)
C4—C5—C6120.5 (2)C16—C21—C20120.24 (18)
C4—C5—H5119.8C16—C21—H21119.9
C6—C5—H5119.8C20—C21—H21119.9
C5—C6—C1118.91 (18)C21—C20—C19119.5 (2)
C5—C6—H6120.5C21—C20—H20120.2
C1—C6—H6120.5C19—C20—H20120.2
C13—C14—C9122.50 (15)C18—C19—C20120.2 (2)
C13—C14—N1130.70 (14)C18—C19—H19119.9
C9—C14—N1106.78 (13)C20—C19—H19119.9
C12—C13—C14117.03 (16)C17—C18—C19120.1 (2)
C12—C13—H13121.5C17—C18—H18120.0
C14—C13—H13121.5C19—C18—H18120.0
C13—C12—C11121.58 (17)C18—C17—C16121.0 (2)
C13—C12—H12119.2C18—C17—H17119.5
C11—C12—H12119.2C16—C17—H17119.5
C10—C11—C12121.37 (17)C7—N1—C14108.35 (12)
C10—C11—H11119.3C7—N1—S1123.27 (10)
C12—C11—H11119.3C14—N1—S1126.91 (10)
C11—C10—C9118.68 (17)O2—S1—O1120.91 (7)
C11—C10—H10120.7O2—S1—N1105.43 (7)
C9—C10—H10120.7O1—S1—N1106.66 (7)
C14—C9—C10118.82 (15)O2—S1—C1108.92 (7)
C14—C9—C8107.78 (14)O1—S1—C1109.22 (7)
C10—C9—C8133.37 (15)N1—S1—C1104.41 (7)
C6—C1—C2—C3−0.4 (3)C8—C15—C16—C21−42.0 (2)
S1—C1—C2—C3178.44 (13)O3—C15—C16—C17−35.9 (2)
C1—C2—C3—C40.2 (3)C8—C15—C16—C17142.89 (16)
C2—C3—C4—C50.2 (3)C17—C16—C21—C201.0 (3)
C3—C4—C5—C6−0.5 (3)C15—C16—C21—C20−174.08 (16)
C4—C5—C6—C10.3 (3)C16—C21—C20—C19−1.4 (3)
C2—C1—C6—C50.2 (3)C21—C20—C19—C181.1 (3)
S1—C1—C6—C5−178.69 (14)C20—C19—C18—C17−0.4 (4)
C9—C14—C13—C120.7 (2)C19—C18—C17—C160.0 (3)
N1—C14—C13—C12178.95 (15)C21—C16—C17—C18−0.3 (3)
C14—C13—C12—C11−1.5 (3)C15—C16—C17—C18175.06 (18)
C13—C12—C11—C101.0 (3)C8—C7—N1—C141.51 (16)
C12—C11—C10—C90.3 (3)C8—C7—N1—S1168.55 (10)
C13—C14—C9—C100.5 (2)C13—C14—N1—C7−179.63 (15)
N1—C14—C9—C10−178.11 (13)C9—C14—N1—C7−1.22 (16)
C13—C14—C9—C8179.08 (14)C13—C14—N1—S113.9 (2)
N1—C14—C9—C80.51 (16)C9—C14—N1—S1−167.65 (10)
C11—C10—C9—C14−1.0 (2)C7—N1—S1—O233.46 (13)
C11—C10—C9—C8−179.16 (16)C14—N1—S1—O2−161.98 (12)
C14—C9—C8—C70.40 (16)C7—N1—S1—O1163.18 (12)
C10—C9—C8—C7178.74 (17)C14—N1—S1—O1−32.27 (14)
C14—C9—C8—C15176.58 (14)C7—N1—S1—C1−81.25 (13)
C10—C9—C8—C15−5.1 (3)C14—N1—S1—C183.30 (13)
C9—C8—C7—N1−1.18 (17)C2—C1—S1—O2155.20 (12)
C15—C8—C7—N1−177.26 (14)C6—C1—S1—O2−25.92 (15)
C7—C8—C15—O3161.36 (17)C2—C1—S1—O121.21 (15)
C9—C8—C15—O3−14.1 (2)C6—C1—S1—O1−159.91 (13)
C7—C8—C15—C16−17.5 (2)C2—C1—S1—N1−92.56 (13)
C9—C8—C15—C16167.13 (14)C6—C1—S1—N186.32 (14)
O3—C15—C16—C21139.19 (18)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.592.934 (2)103
C10—H10···O30.932.573.068 (3)114
C13—H13···O10.932.422.999 (2)120
C6—H6···O2i0.932.583.493 (2)167
C7—H7···O2i0.932.543.429 (2)160
C4—H4···Cg1ii0.932.983.774 (3)144

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5379).

References

  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.
  • Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography