(2-Methyl-1-phenyl-sulfonyl-1H-indol-3-yl)methanol.

In the title compound, C(16)H(15)NO(3)S, 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 mol-ecules 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 = 301.35

Triclinic,

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[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 ▶); 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.

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

C16H15NO3S	Z = 2
Mr = 301.35	F000 = 316
Triclinic, P1	Dx = 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 = 2.7–26.2º
c = 9.9630 (4) Å	µ = 0.23 mm−1
α = 78.718 (2)º	T = 295 (2) K
β = 65.347 (3)º	Block, colourless
γ = 78.884 (2)º	0.22 × 0.18 × 0.16 mm
V = 715.77 (6) Å3

Bruker Kappa APEXII diffractometer	4088 independent reflections
Radiation source: fine-focus sealed tube	3267 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 295(2) K	θmax = 30.0º
ω and φ scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.920, Tmax = 0.963	k = −13→13
14857 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058	H-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 reflections	Δρmax = 0.43 e Å−3
191 parameters	Δρmin = −0.48 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .