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

Chakkaravarthi, G.; Dhayalan, V.; Mohanakrishnan, A.K.; Manivannan, V.

doi:10.1107/S1600536808003024

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o542

doi:10.1107/S1600536808003024

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

G. Chakkaravarthi,^a ^* V. Dhayalan,^b A. K. Mohanakrishnan ^b and V. Manivannan ^c

^aDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 6 December 2007; accepted 28 January 2008; online 30 January 2008)

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 ); Pomarnacka & Kozlarska-Kedra (2003 ). For the structure of closely related compounds, see: Chakkaravarthi et al. (2007 ); Liu et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₅NO₃S
M_r = 301.35
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.058
wR(F²) = 0.241
S = 1.05
4088 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.82	2.59	3.276 (5)	142
Symmetry code: (i) x+1, y, z.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003024/ya2066sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

	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.

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

Crystal data top

C₁₆H₁₅NO₃S	Z = 2
M_r = 301.35	F(000) = 316
Triclinic, P1	D_x = 1.398 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3780 (4) Å	Cell parameters from 8443 reflections
b = 9.6969 (5) Å	θ = 2.7–26.2°
c = 9.9630 (4) Å	µ = 0.23 mm⁻¹
α = 78.718 (2)°	T = 295 K
β = 65.347 (3)°	Block, colourless
γ = 78.884 (2)°	0.22 × 0.18 × 0.16 mm
V = 715.77 (6) Å³

Data collection top

Bruker Kappa APEXII diffractometer	4088 independent reflections
Radiation source: fine-focus sealed tube	3267 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω and ϕ scans	θ_max = 30.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.920, T_max = 0.963	k = −13→13
14857 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.241	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0931P)² + 0.2366P] where P = (F_o² + 2F_c²)/3
4088 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₁₆H₁₅NO₃S	γ = 78.884 (2)°
M_r = 301.35	V = 715.77 (6) Å³
Triclinic, P1	Z = 2
a = 8.3780 (4) Å	Mo Kα radiation
b = 9.6969 (5) Å	µ = 0.23 mm⁻¹
c = 9.9630 (4) Å	T = 295 K
α = 78.718 (2)°	0.22 × 0.18 × 0.16 mm
β = 65.347 (3)°

Data collection top

Bruker Kappa APEXII diffractometer	4088 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3267 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.963	R_int = 0.021
14857 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.241	H-atom parameters constrained
S = 1.05	Δρ_max = 0.43 e Å⁻³
4088 reflections	Δρ_min = −0.48 e Å⁻³
191 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.70206 (7)	0.26671 (6)	0.24015 (6)	0.0505 (2)
O1	0.7232 (3)	0.1941 (2)	0.1217 (2)	0.0682 (6)
O2	0.5477 (2)	0.3641 (2)	0.2984 (3)	0.0705 (6)
O3	1.1581 (6)	0.5512 (4)	0.3706 (4)	0.1316 (14)
H3	1.2640	0.5450	0.3519	0.197*
N1	0.8742 (2)	0.35733 (18)	0.17689 (19)	0.0434 (4)
C1	0.7297 (3)	0.1424 (2)	0.3853 (2)	0.0464 (4)
C2	0.7397 (5)	0.0001 (3)	0.3817 (4)	0.0705 (8)
H2	0.7350	−0.0317	0.3013	0.085*
C3	0.7567 (6)	−0.0952 (3)	0.4989 (4)	0.0831 (10)
H3A	0.7620	−0.1917	0.4982	0.100*
C4	0.7657 (4)	−0.0484 (3)	0.6162 (3)	0.0709 (8)
H4	0.7779	−0.1133	0.6946	0.085*
C5	0.7569 (5)	0.0929 (3)	0.6185 (3)	0.0705 (8)
H5	0.7647	0.1236	0.6981	0.085*
C6	0.7364 (4)	0.1917 (3)	0.5037 (3)	0.0594 (6)
H6	0.7275	0.2883	0.5064	0.071*
C7	0.8842 (3)	0.4756 (2)	0.2371 (2)	0.0449 (4)
C8	1.0560 (3)	0.4853 (2)	0.2018 (2)	0.0453 (4)
C9	1.1626 (3)	0.3694 (2)	0.1214 (2)	0.0413 (4)
C10	1.3442 (3)	0.3292 (3)	0.0597 (3)	0.0537 (5)
H10	1.4219	0.3825	0.0652	0.064*
C11	1.4065 (4)	0.2092 (3)	−0.0093 (3)	0.0594 (6)
H11	1.5275	0.1794	−0.0481	0.071*
C12	1.2929 (4)	0.1321 (3)	−0.0224 (3)	0.0615 (6)
H12	1.3393	0.0523	−0.0718	0.074*
C13	1.1125 (4)	0.1701 (2)	0.0358 (3)	0.0525 (5)
H13	1.0363	0.1171	0.0277	0.063*
C14	1.0485 (3)	0.2911 (2)	0.1073 (2)	0.0400 (4)
C15	0.7267 (4)	0.5750 (3)	0.3152 (3)	0.0650 (7)
H15A	0.6612	0.5303	0.4133	0.097*
H15B	0.6525	0.5993	0.2601	0.097*
H15C	0.7648	0.6594	0.3226	0.097*
C16	1.1300 (4)	0.5945 (3)	0.2393 (3)	0.0649 (7)
H16A	1.2413	0.6143	0.1580	0.078*
H16B	1.0488	0.6816	0.2494	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0467 (3)	0.0609 (4)	0.0548 (4)	−0.0134 (2)	−0.0299 (3)	−0.0024 (2)
O1	0.0776 (13)	0.0891 (14)	0.0633 (11)	−0.0306 (11)	−0.0455 (10)	−0.0057 (10)
O2	0.0440 (9)	0.0813 (13)	0.0859 (14)	−0.0033 (9)	−0.0311 (9)	−0.0021 (11)
O3	0.224 (4)	0.128 (3)	0.104 (2)	−0.087 (3)	−0.104 (2)	0.0019 (19)
N1	0.0453 (9)	0.0437 (8)	0.0451 (9)	−0.0082 (7)	−0.0214 (7)	−0.0037 (6)
C1	0.0469 (10)	0.0499 (10)	0.0458 (10)	−0.0151 (8)	−0.0192 (8)	−0.0027 (8)
C2	0.100 (2)	0.0570 (14)	0.0674 (16)	−0.0225 (14)	−0.0387 (16)	−0.0107 (12)
C3	0.122 (3)	0.0477 (13)	0.081 (2)	−0.0179 (16)	−0.043 (2)	0.0014 (13)
C4	0.085 (2)	0.0636 (15)	0.0549 (14)	−0.0142 (14)	−0.0242 (13)	0.0098 (11)
C5	0.094 (2)	0.0730 (17)	0.0455 (12)	−0.0156 (15)	−0.0283 (13)	−0.0044 (11)
C6	0.0810 (17)	0.0508 (12)	0.0519 (12)	−0.0122 (11)	−0.0300 (12)	−0.0066 (9)
C7	0.0538 (11)	0.0378 (9)	0.0425 (9)	−0.0039 (8)	−0.0198 (8)	−0.0041 (7)
C8	0.0566 (12)	0.0404 (9)	0.0430 (9)	−0.0100 (8)	−0.0218 (9)	−0.0055 (7)
C9	0.0468 (10)	0.0430 (9)	0.0384 (8)	−0.0086 (7)	−0.0207 (8)	−0.0031 (7)
C10	0.0458 (11)	0.0631 (13)	0.0558 (12)	−0.0105 (10)	−0.0229 (10)	−0.0058 (10)
C11	0.0522 (13)	0.0661 (14)	0.0540 (12)	0.0030 (11)	−0.0202 (10)	−0.0070 (11)
C12	0.0697 (16)	0.0582 (13)	0.0569 (13)	0.0096 (11)	−0.0272 (12)	−0.0205 (10)
C13	0.0667 (14)	0.0486 (11)	0.0529 (11)	−0.0072 (10)	−0.0307 (10)	−0.0137 (9)
C14	0.0472 (10)	0.0410 (9)	0.0363 (8)	−0.0073 (7)	−0.0210 (7)	−0.0023 (7)
C15	0.0632 (15)	0.0511 (12)	0.0709 (16)	0.0048 (11)	−0.0186 (12)	−0.0157 (11)
C16	0.0821 (18)	0.0538 (13)	0.0680 (15)	−0.0242 (13)	−0.0294 (13)	−0.0134 (11)

Geometric parameters (Å, º) top

S1—O2	1.421 (2)	C7—C8	1.350 (3)
S1—O1	1.422 (2)	C7—C15	1.491 (3)
S1—N1	1.6619 (18)	C8—C9	1.439 (3)
S1—C1	1.757 (2)	C8—C16	1.499 (3)
O3—C16	1.396 (4)	C9—C10	1.389 (3)
O3—H3	0.8200	C9—C14	1.394 (3)
N1—C14	1.412 (3)	C10—C11	1.371 (4)
N1—C7	1.425 (3)	C10—H10	0.9300
C1—C2	1.373 (4)	C11—C12	1.377 (4)
C1—C6	1.382 (3)	C11—H11	0.9300
C2—C3	1.380 (4)	C12—C13	1.377 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.368 (5)	C13—C14	1.391 (3)
C3—H3A	0.9300	C13—H13	0.9300
C4—C5	1.362 (5)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.388 (4)	C15—H15C	0.9600
C5—H5	0.9300	C16—H16A	0.9700
C6—H6	0.9300	C16—H16B	0.9700

O2—S1—O1	119.32 (13)	C7—C8—C16	127.6 (2)
O2—S1—N1	106.85 (11)	C9—C8—C16	123.9 (2)
O1—S1—N1	106.16 (11)	C10—C9—C14	119.9 (2)
O2—S1—C1	109.90 (12)	C10—C9—C8	132.5 (2)
O1—S1—C1	109.10 (12)	C14—C9—C8	107.59 (18)
N1—S1—C1	104.41 (9)	C11—C10—C9	118.6 (2)
C16—O3—H3	109.5	C11—C10—H10	120.7
C14—N1—C7	107.57 (17)	C9—C10—H10	120.7
C14—N1—S1	120.92 (14)	C10—C11—C12	121.1 (2)
C7—N1—S1	125.77 (15)	C10—C11—H11	119.4
C2—C1—C6	121.3 (2)	C12—C11—H11	119.4
C2—C1—S1	120.2 (2)	C13—C12—C11	121.6 (2)
C6—C1—S1	118.42 (18)	C13—C12—H12	119.2
C1—C2—C3	119.1 (3)	C11—C12—H12	119.2
C1—C2—H2	120.4	C12—C13—C14	117.4 (2)
C3—C2—H2	120.4	C12—C13—H13	121.3
C4—C3—C2	120.4 (3)	C14—C13—H13	121.3
C4—C3—H3A	119.8	C13—C14—C9	121.3 (2)
C2—C3—H3A	119.8	C13—C14—N1	131.2 (2)
C5—C4—C3	120.1 (3)	C9—C14—N1	107.57 (17)
C5—C4—H4	119.9	C7—C15—H15A	109.5
C3—C4—H4	119.9	C7—C15—H15B	109.5
C4—C5—C6	120.9 (3)	H15A—C15—H15B	109.5
C4—C5—H5	119.5	C7—C15—H15C	109.5
C6—C5—H5	119.5	H15A—C15—H15C	109.5
C1—C6—C5	118.1 (2)	H15B—C15—H15C	109.5
C1—C6—H6	121.0	O3—C16—C8	112.6 (2)
C5—C6—H6	121.0	O3—C16—H16A	109.1
C8—C7—N1	108.74 (19)	C8—C16—H16A	109.1
C8—C7—C15	127.7 (2)	O3—C16—H16B	109.1
N1—C7—C15	123.4 (2)	C8—C16—H16B	109.1
C7—C8—C9	108.49 (19)	H16A—C16—H16B	107.8

O2—S1—N1—C14	−178.08 (15)	C15—C7—C8—C9	−177.5 (2)
O1—S1—N1—C14	−49.73 (17)	N1—C7—C8—C16	178.9 (2)
C1—S1—N1—C14	65.49 (17)	C15—C7—C8—C16	3.4 (4)
O2—S1—N1—C7	32.0 (2)	C7—C8—C9—C10	180.0 (2)
O1—S1—N1—C7	160.38 (18)	C16—C8—C9—C10	−0.9 (4)
C1—S1—N1—C7	−84.39 (18)	C7—C8—C9—C14	1.1 (2)
O2—S1—C1—C2	123.0 (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—C11	178.9 (2)
O2—S1—C1—C6	−55.4 (2)	C9—C10—C11—C12	2.2 (4)
O1—S1—C1—C6	172.0 (2)	C10—C11—C12—C13	−1.4 (4)
N1—S1—C1—C6	58.9 (2)	C11—C12—C13—C14	0.7 (4)
C6—C1—C2—C3	0.0 (5)	C12—C13—C14—C9	−0.9 (3)
S1—C1—C2—C3	−178.3 (3)	C12—C13—C14—N1	179.7 (2)
C1—C2—C3—C4	−0.8 (6)	C10—C9—C14—C13	1.8 (3)
C2—C3—C4—C5	0.4 (6)	C8—C9—C14—C13	−179.15 (18)
C3—C4—C5—C6	0.8 (5)	C10—C9—C14—N1	−178.74 (18)
C2—C1—C6—C5	1.1 (4)	C8—C9—C14—N1	0.3 (2)
S1—C1—C6—C5	179.5 (2)	C7—N1—C14—C13	177.9 (2)
C4—C5—C6—C1	−1.6 (5)	S1—N1—C14—C13	23.2 (3)
C14—N1—C7—C8	2.2 (2)	C7—N1—C14—C9	−1.5 (2)
S1—N1—C7—C8	155.38 (16)	S1—N1—C14—C9	−156.26 (14)
C14—N1—C7—C15	178.0 (2)	C7—C8—C16—O3	93.7 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	2.59	3.276 (5)	142

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅NO₃S
M_r	301.35
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.3780 (4), 9.6969 (5), 9.9630 (4)
α, β, γ (°)	78.718 (2), 65.347 (3), 78.884 (2)
V (Å³)	715.77 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.22 × 0.18 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.920, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	14857, 4088, 3267
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.241, 1.05
No. of reflections	4088
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.48

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	2.59	3.276 (5)	142

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

Acknowledgements

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

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