PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o542.
Published online 2008 January 30. doi:  10.1107/S1600536808003024
PMCID: PMC2960400

(2-Methyl-1-phenyl­sulfonyl-1H-indol-3-yl)methanol

Abstract

In the title compound, C16H15NO3S, the plane of the phenyl ring forms a dihedral angle of 80.37 (8)° with the indole ring system. The crystal packing is stabilized by weak O—H(...)O hydrogen bonds which link the mol­ecules into infinite chains along the a axis of the crystal.

Related literature

For biological activity, see: Nieto et al. (2005 [triangle]); Pomarnacka & Kozlarska-Kedra (2003 [triangle]). For the structure of closely related compounds, see: Chakkaravarthi et al. (2007 [triangle]); Liu et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o542-scheme1.jpg

Experimental

Crystal data

  • C16H15NO3S
  • M r = 301.35
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o542-efi1.jpg
  • a = 8.3780 (4) Å
  • b = 9.6969 (5) Å
  • c = 9.9630 (4) Å
  • α = 78.718 (2)°
  • β = 65.347 (3)°
  • γ = 78.884 (2)°
  • V = 715.77 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 295 (2) K
  • 0.22 × 0.18 × 0.16 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.920, T max = 0.963
  • 14857 measured reflections
  • 4088 independent reflections
  • 3267 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.241
  • S = 1.05
  • 4088 reflections
  • 191 parameters
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.48 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/S1600536808003024/ya2066sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003024/ya2066Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

In continuation of our studies of benzenesulfonamide derivatives, which are known to exhibit antibacterial (Nieto et al., 2005), anticancer and anti - HIV (Pomarnacka & Kozlarska-Kedra, 2003) activities, we determined the crystal structure of the title compound, (I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with those reported for similar structures (Chakkaravarthi et al., 2007; Liu et al., 2007).

The plane of the phenyl ring forms the dihedral angle of 80.37 (8)° with the indole ring system. The N1—S1—C1 plane is also approximately orthogonal to indole (dihedral angle 79.21 (6)°) and makes an angle of 57.86 (11)° with the phenyl plane.

The crystal packing of (I) is stabilized by a rather weak O—H···O bonds which link the molecules into the infinite chains along the x-axis of the crystal (Fig. 2, Table 2).

Experimental

Benzenesulfonyl chloride (7.75 ml, 43.9 mmol), 60% NaOH solution (60 g in 100 ml), along with tetrabutylammonium hydrogensulfate (1.5 g) were added to the solution of 2-methylindole-3-carboxaldehyde (8.0 g, 50.3 mmol) in distilled benzene (200 ml). The two-phase system thus formed was stirred at room temperature for 2 h. It was then diluted with water (200 ml) and the organic layer was separated. The aqueous layer was extracted with benzene (two times by 30 ml). The combined organic layer was dried (Na2SO4). The benzene was then completely removed and the crude product was recrystallized from methanol to get 1-phenylsulfonyl-2-methylindole-3-carboxaldehyde.

NaBH4 (2.97 g, 78.60 mmol) was added slowly to a solution of 1-phenylsulfonyl-2-methylindole-3-carboxaldehyde (3 g, 13.10 mmol) in THF (30 ml). The reaction mixture was stirred at room temperature for 3 hrs. Dilute HCl (10%) was cautiously added until the solution became acidic. After most of the THF was removed in vacuo, the solution was extracted with dichloromethane and dried (MgSO4); the solvent was then removed under vacuo. The crude product thus obtained was recrystallized from 10% ethyl acetate/n-hexane.

Refinement

H atoms were positioned geometrically and refined using riding model approximation 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, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3 and O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O) for OH. The hydroxyl O3 atom showed rather high thermal displacement parameters, however the attempts to introduce an alternative position and refine disordered model proved unsuccessful.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids; H atoms are shown as small spheres of arbitrary radius.
Fig. 2.
The packing of (I), viewed down the c axis. H-bonds are shown as dashed lines; H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C16H15NO3SZ = 2
Mr = 301.35F000 = 316
Triclinic, P1Dx = 1.398 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.3780 (4) ÅCell parameters from 8443 reflections
b = 9.6969 (5) Åθ = 2.7–26.2º
c = 9.9630 (4) ŵ = 0.23 mm1
α = 78.718 (2)ºT = 295 (2) K
β = 65.347 (3)ºBlock, colourless
γ = 78.884 (2)º0.22 × 0.18 × 0.16 mm
V = 715.77 (6) Å3

Data collection

Bruker Kappa APEXII diffractometer4088 independent reflections
Radiation source: fine-focus sealed tube3267 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 295(2) Kθmax = 30.0º
ω and [var phi] scansθmin = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.920, Tmax = 0.963k = −13→13
14857 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.241  w = 1/[σ2(Fo2) + (0.0931P)2 + 0.2366P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4088 reflectionsΔρmax = 0.43 e Å3
191 parametersΔρmin = −0.48 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/Ueq
S10.70206 (7)0.26671 (6)0.24015 (6)0.0505 (2)
O10.7232 (3)0.1941 (2)0.1217 (2)0.0682 (6)
O20.5477 (2)0.3641 (2)0.2984 (3)0.0705 (6)
O31.1581 (6)0.5512 (4)0.3706 (4)0.1316 (14)
H31.26400.54500.35190.197*
N10.8742 (2)0.35733 (18)0.17689 (19)0.0434 (4)
C10.7297 (3)0.1424 (2)0.3853 (2)0.0464 (4)
C20.7397 (5)0.0001 (3)0.3817 (4)0.0705 (8)
H20.7350−0.03170.30130.085*
C30.7567 (6)−0.0952 (3)0.4989 (4)0.0831 (10)
H3A0.7620−0.19170.49820.100*
C40.7657 (4)−0.0484 (3)0.6162 (3)0.0709 (8)
H40.7779−0.11330.69460.085*
C50.7569 (5)0.0929 (3)0.6185 (3)0.0705 (8)
H50.76470.12360.69810.085*
C60.7364 (4)0.1917 (3)0.5037 (3)0.0594 (6)
H60.72750.28830.50640.071*
C70.8842 (3)0.4756 (2)0.2371 (2)0.0449 (4)
C81.0560 (3)0.4853 (2)0.2018 (2)0.0453 (4)
C91.1626 (3)0.3694 (2)0.1214 (2)0.0413 (4)
C101.3442 (3)0.3292 (3)0.0597 (3)0.0537 (5)
H101.42190.38250.06520.064*
C111.4065 (4)0.2092 (3)−0.0093 (3)0.0594 (6)
H111.52750.1794−0.04810.071*
C121.2929 (4)0.1321 (3)−0.0224 (3)0.0615 (6)
H121.33930.0523−0.07180.074*
C131.1125 (4)0.1701 (2)0.0358 (3)0.0525 (5)
H131.03630.11710.02770.063*
C141.0485 (3)0.2911 (2)0.1073 (2)0.0400 (4)
C150.7267 (4)0.5750 (3)0.3152 (3)0.0650 (7)
H15A0.66120.53030.41330.097*
H15B0.65250.59930.26010.097*
H15C0.76480.65940.32260.097*
C161.1300 (4)0.5945 (3)0.2393 (3)0.0649 (7)
H16A1.24130.61430.15800.078*
H16B1.04880.68160.24940.078*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0467 (3)0.0609 (4)0.0548 (4)−0.0134 (2)−0.0299 (3)−0.0024 (2)
O10.0776 (13)0.0891 (14)0.0633 (11)−0.0306 (11)−0.0455 (10)−0.0057 (10)
O20.0440 (9)0.0813 (13)0.0859 (14)−0.0033 (9)−0.0311 (9)−0.0021 (11)
O30.224 (4)0.128 (3)0.104 (2)−0.087 (3)−0.104 (2)0.0019 (19)
N10.0453 (9)0.0437 (8)0.0451 (9)−0.0082 (7)−0.0214 (7)−0.0037 (6)
C10.0469 (10)0.0499 (10)0.0458 (10)−0.0151 (8)−0.0192 (8)−0.0027 (8)
C20.100 (2)0.0570 (14)0.0674 (16)−0.0225 (14)−0.0387 (16)−0.0107 (12)
C30.122 (3)0.0477 (13)0.081 (2)−0.0179 (16)−0.043 (2)0.0014 (13)
C40.085 (2)0.0636 (15)0.0549 (14)−0.0142 (14)−0.0242 (13)0.0098 (11)
C50.094 (2)0.0730 (17)0.0455 (12)−0.0156 (15)−0.0283 (13)−0.0044 (11)
C60.0810 (17)0.0508 (12)0.0519 (12)−0.0122 (11)−0.0300 (12)−0.0066 (9)
C70.0538 (11)0.0378 (9)0.0425 (9)−0.0039 (8)−0.0198 (8)−0.0041 (7)
C80.0566 (12)0.0404 (9)0.0430 (9)−0.0100 (8)−0.0218 (9)−0.0055 (7)
C90.0468 (10)0.0430 (9)0.0384 (8)−0.0086 (7)−0.0207 (8)−0.0031 (7)
C100.0458 (11)0.0631 (13)0.0558 (12)−0.0105 (10)−0.0229 (10)−0.0058 (10)
C110.0522 (13)0.0661 (14)0.0540 (12)0.0030 (11)−0.0202 (10)−0.0070 (11)
C120.0697 (16)0.0582 (13)0.0569 (13)0.0096 (11)−0.0272 (12)−0.0205 (10)
C130.0667 (14)0.0486 (11)0.0529 (11)−0.0072 (10)−0.0307 (10)−0.0137 (9)
C140.0472 (10)0.0410 (9)0.0363 (8)−0.0073 (7)−0.0210 (7)−0.0023 (7)
C150.0632 (15)0.0511 (12)0.0709 (16)0.0048 (11)−0.0186 (12)−0.0157 (11)
C160.0821 (18)0.0538 (13)0.0680 (15)−0.0242 (13)−0.0294 (13)−0.0134 (11)

Geometric parameters (Å, °)

S1—O21.421 (2)C7—C81.350 (3)
S1—O11.422 (2)C7—C151.491 (3)
S1—N11.6619 (18)C8—C91.439 (3)
S1—C11.757 (2)C8—C161.499 (3)
O3—C161.396 (4)C9—C101.389 (3)
O3—H30.8200C9—C141.394 (3)
N1—C141.412 (3)C10—C111.371 (4)
N1—C71.425 (3)C10—H100.9300
C1—C21.373 (4)C11—C121.377 (4)
C1—C61.382 (3)C11—H110.9300
C2—C31.380 (4)C12—C131.377 (4)
C2—H20.9300C12—H120.9300
C3—C41.368 (5)C13—C141.391 (3)
C3—H3A0.9300C13—H130.9300
C4—C51.362 (5)C15—H15A0.9600
C4—H40.9300C15—H15B0.9600
C5—C61.388 (4)C15—H15C0.9600
C5—H50.9300C16—H16A0.9700
C6—H60.9300C16—H16B0.9700
O2—S1—O1119.32 (13)C7—C8—C16127.6 (2)
O2—S1—N1106.85 (11)C9—C8—C16123.9 (2)
O1—S1—N1106.16 (11)C10—C9—C14119.9 (2)
O2—S1—C1109.90 (12)C10—C9—C8132.5 (2)
O1—S1—C1109.10 (12)C14—C9—C8107.59 (18)
N1—S1—C1104.41 (9)C11—C10—C9118.6 (2)
C16—O3—H3109.5C11—C10—H10120.7
C14—N1—C7107.57 (17)C9—C10—H10120.7
C14—N1—S1120.92 (14)C10—C11—C12121.1 (2)
C7—N1—S1125.77 (15)C10—C11—H11119.4
C2—C1—C6121.3 (2)C12—C11—H11119.4
C2—C1—S1120.2 (2)C13—C12—C11121.6 (2)
C6—C1—S1118.42 (18)C13—C12—H12119.2
C1—C2—C3119.1 (3)C11—C12—H12119.2
C1—C2—H2120.4C12—C13—C14117.4 (2)
C3—C2—H2120.4C12—C13—H13121.3
C4—C3—C2120.4 (3)C14—C13—H13121.3
C4—C3—H3A119.8C13—C14—C9121.3 (2)
C2—C3—H3A119.8C13—C14—N1131.2 (2)
C5—C4—C3120.1 (3)C9—C14—N1107.57 (17)
C5—C4—H4119.9C7—C15—H15A109.5
C3—C4—H4119.9C7—C15—H15B109.5
C4—C5—C6120.9 (3)H15A—C15—H15B109.5
C4—C5—H5119.5C7—C15—H15C109.5
C6—C5—H5119.5H15A—C15—H15C109.5
C1—C6—C5118.1 (2)H15B—C15—H15C109.5
C1—C6—H6121.0O3—C16—C8112.6 (2)
C5—C6—H6121.0O3—C16—H16A109.1
C8—C7—N1108.74 (19)C8—C16—H16A109.1
C8—C7—C15127.7 (2)O3—C16—H16B109.1
N1—C7—C15123.4 (2)C8—C16—H16B109.1
C7—C8—C9108.49 (19)H16A—C16—H16B107.8
O2—S1—N1—C14−178.08 (15)C15—C7—C8—C9−177.5 (2)
O1—S1—N1—C14−49.73 (17)N1—C7—C8—C16178.9 (2)
C1—S1—N1—C1465.49 (17)C15—C7—C8—C163.4 (4)
O2—S1—N1—C732.0 (2)C7—C8—C9—C10180.0 (2)
O1—S1—N1—C7160.38 (18)C16—C8—C9—C10−0.9 (4)
C1—S1—N1—C7−84.39 (18)C7—C8—C9—C141.1 (2)
O2—S1—C1—C2123.0 (3)C16—C8—C9—C14−179.8 (2)
O1—S1—C1—C2−9.6 (3)C14—C9—C10—C11−2.3 (3)
N1—S1—C1—C2−122.7 (2)C8—C9—C10—C11178.9 (2)
O2—S1—C1—C6−55.4 (2)C9—C10—C11—C122.2 (4)
O1—S1—C1—C6172.0 (2)C10—C11—C12—C13−1.4 (4)
N1—S1—C1—C658.9 (2)C11—C12—C13—C140.7 (4)
C6—C1—C2—C30.0 (5)C12—C13—C14—C9−0.9 (3)
S1—C1—C2—C3−178.3 (3)C12—C13—C14—N1179.7 (2)
C1—C2—C3—C4−0.8 (6)C10—C9—C14—C131.8 (3)
C2—C3—C4—C50.4 (6)C8—C9—C14—C13−179.15 (18)
C3—C4—C5—C60.8 (5)C10—C9—C14—N1−178.74 (18)
C2—C1—C6—C51.1 (4)C8—C9—C14—N10.3 (2)
S1—C1—C6—C5179.5 (2)C7—N1—C14—C13177.9 (2)
C4—C5—C6—C1−1.6 (5)S1—N1—C14—C1323.2 (3)
C14—N1—C7—C82.2 (2)C7—N1—C14—C9−1.5 (2)
S1—N1—C7—C8155.38 (16)S1—N1—C14—C9−156.26 (14)
C14—N1—C7—C15178.0 (2)C7—C8—C16—O393.7 (4)
S1—N1—C7—C15−28.9 (3)C9—C8—C16—O3−85.2 (3)
N1—C7—C8—C9−2.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.822.593.276 (5)142

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2066).

References

  • 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.
  • Liu, Y., Gribble, G. W. & Jasinski, J. P. (2007). Acta Cryst. E63, o738–o740.
  • Nieto, M. J., Alovero, F. L., Manzo, R. H. & Mazzieri, M. R. (2005). Eur. J. Med. Chem.40, 361–369. [PubMed]
  • Pomarnacka, E. & Kozlarska-Kedra, I. (2003). Il Farmaco, 58, 423–429. [PubMed]
  • 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.

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