3-Iodo-2-methyl-1-phenyl-sulfonyl-1H-indole.

In the title compound, C(15)H(12)INO(2)S, the sulfonyl-bound phenyl ring forms a dihedral angle 82.84 (9)° with the indole ring system. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O hydrogen bond. The crystal structure exhibits weak inter-molecular C-H⋯π inter-actions and π-π inter-actions between the indole groups [centroid-centroid distance between the five-membered and six-membered rings of the indole group = 3.7617 (18) Å].

Related literature

For the biological properties of indole derivatives, see: Chai et al. (2006 ▶); Nieto et al. (2005 ▶). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C15H12INO2S

M = 397.22

Monoclinic,

a = 10.7068 (3) Å

b = 16.2670 (4) Å

c = 8.5147 (2) Å

β = 104.540 (1)°

V = 1435.49 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.38 mm−1

T = 295 K

0.30 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.536, T max = 0.648

21249 measured reflections

5276 independent reflections

3696 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.144

S = 1.06

5276 reflections

182 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −1.56 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004685/gk2346sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004685/gk2346Isup2.hkl

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

C15H12INO2S	F(000) = 776
Mr = 397.22	Dx = 1.838 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8510 reflections
a = 10.7068 (3) Å	θ = 2.5–30.4°
b = 16.2670 (4) Å	µ = 2.38 mm−1
c = 8.5147 (2) Å	T = 295 K
β = 104.540 (1)°	Block, colourless
V = 1435.49 (6) Å3	0.30 × 0.24 × 0.20 mm
Z = 4

Bruker Kappa APEXII diffractometer	5276 independent reflections
Radiation source: fine-focus sealed tube	3696 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scans	θmax = 32.8°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→16
Tmin = 0.536, Tmax = 0.648	k = −23→24
21249 measured reflections	l = −12→11

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0743P)2 + 0.987P] where P = (Fo2 + 2Fc2)/3
5276 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.94 e Å−3
1 restraint	Δρmin = −1.56 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.8489 (3)	0.14775 (16)	0.8788 (3)	0.0350 (5)
C2	0.8848 (4)	0.0951 (2)	1.0097 (4)	0.0495 (7)
H2	0.8265	0.0574	1.0324	0.059*
C3	1.0098 (4)	0.0998 (3)	1.1063 (5)	0.0638 (10)
H3	1.0365	0.0646	1.1944	0.077*
C4	1.0940 (4)	0.1562 (3)	1.0722 (5)	0.0643 (11)
H4	1.1778	0.1587	1.1375	0.077*
C5	1.0569 (3)	0.2092 (3)	0.9431 (5)	0.0556 (9)
H5	1.1149	0.2478	0.9227	0.067*
C6	0.9331 (3)	0.20492 (19)	0.8436 (4)	0.0433 (6)
H6	0.9073	0.2398	0.7549	0.052*
C7	0.7397 (3)	0.04833 (16)	0.5161 (3)	0.0329 (5)
C8	0.7262 (3)	−0.03190 (16)	0.4724 (3)	0.0336 (5)
C9	0.6619 (2)	−0.07527 (14)	0.5739 (3)	0.0297 (4)
C10	0.6230 (3)	−0.15718 (17)	0.5777 (4)	0.0387 (6)
H10	0.6379	−0.1950	0.5025	0.046*
C11	0.5626 (3)	−0.1805 (2)	0.6940 (4)	0.0478 (7)
H11	0.5362	−0.2348	0.6978	0.057*
C12	0.5402 (3)	−0.1249 (2)	0.8061 (4)	0.0486 (7)
H12	0.5005	−0.1429	0.8852	0.058*
C13	0.5753 (3)	−0.0428 (2)	0.8043 (4)	0.0435 (6)
H13	0.5585	−0.0055	0.8792	0.052*
C14	0.6367 (2)	−0.01869 (15)	0.6857 (3)	0.0309 (5)
C15	0.7993 (4)	0.1168 (2)	0.4432 (5)	0.0509 (7)
H15A	0.8230	0.0972	0.3483	0.076*
H15B	0.8748	0.1362	0.5208	0.076*
H15C	0.7383	0.1609	0.4137	0.076*
N1	0.6822 (2)	0.05838 (13)	0.6481 (3)	0.0335 (4)
O1	0.6046 (2)	0.13114 (15)	0.8577 (4)	0.0552 (6)
O2	0.6719 (2)	0.21172 (13)	0.6496 (3)	0.0533 (6)
S1	0.68958 (6)	0.14402 (4)	0.75748 (10)	0.03797 (16)
I1	0.78752 (3)	−0.084909 (16)	0.28650 (3)	0.06383 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0355 (12)	0.0307 (11)	0.0379 (13)	0.0043 (9)	0.0078 (10)	−0.0078 (10)
C2	0.0583 (19)	0.0487 (17)	0.0391 (15)	0.0014 (14)	0.0076 (14)	0.0020 (12)
C3	0.071 (3)	0.070 (2)	0.0421 (18)	0.020 (2)	−0.0008 (17)	0.0018 (17)
C4	0.0421 (17)	0.087 (3)	0.056 (2)	0.0121 (17)	−0.0013 (15)	−0.025 (2)
C5	0.0409 (16)	0.065 (2)	0.061 (2)	−0.0088 (14)	0.0131 (14)	−0.0205 (18)
C6	0.0436 (15)	0.0406 (14)	0.0458 (15)	−0.0039 (11)	0.0117 (12)	−0.0062 (12)
C7	0.0368 (12)	0.0290 (11)	0.0337 (12)	−0.0026 (9)	0.0107 (9)	0.0026 (9)
C8	0.0411 (13)	0.0293 (11)	0.0303 (11)	−0.0013 (9)	0.0088 (9)	0.0012 (8)
C9	0.0297 (11)	0.0280 (11)	0.0287 (11)	−0.0016 (8)	0.0025 (8)	0.0014 (8)
C10	0.0444 (14)	0.0295 (12)	0.0376 (13)	−0.0067 (10)	0.0021 (11)	−0.0005 (10)
C11	0.0440 (15)	0.0395 (15)	0.0552 (17)	−0.0157 (12)	0.0036 (13)	0.0100 (13)
C12	0.0407 (15)	0.0578 (19)	0.0489 (17)	−0.0109 (13)	0.0143 (12)	0.0130 (15)
C13	0.0415 (14)	0.0501 (16)	0.0427 (15)	−0.0046 (12)	0.0178 (12)	0.0006 (12)
C14	0.0272 (10)	0.0321 (11)	0.0326 (11)	−0.0008 (8)	0.0058 (9)	0.0005 (9)
C15	0.064 (2)	0.0396 (15)	0.0548 (18)	−0.0110 (14)	0.0261 (15)	0.0073 (14)
N1	0.0389 (11)	0.0255 (9)	0.0373 (11)	−0.0027 (8)	0.0120 (9)	−0.0033 (8)
O1	0.0433 (11)	0.0543 (13)	0.0750 (17)	0.0013 (10)	0.0278 (11)	−0.0227 (12)
O2	0.0528 (13)	0.0308 (10)	0.0659 (15)	0.0113 (9)	−0.0047 (11)	0.0013 (10)
S1	0.0335 (3)	0.0299 (3)	0.0491 (4)	0.0048 (2)	0.0078 (3)	−0.0079 (3)
I1	0.0954 (2)	0.05448 (17)	0.05233 (17)	0.00090 (11)	0.03859 (15)	−0.00527 (9)

C1—C6	1.380 (4)	C9—C14	1.399 (4)
C1—C2	1.381 (4)	C9—C10	1.399 (3)
C1—S1	1.759 (3)	C10—C11	1.365 (5)
C2—C3	1.386 (6)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.379 (5)
C3—C4	1.367 (7)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.387 (5)
C4—C5	1.375 (6)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.392 (4)
C5—C6	1.384 (5)	C13—H13	0.9300
C5—H5	0.9300	C14—N1	1.411 (3)
C6—H6	0.9300	C15—H15A	0.9600
C7—C8	1.355 (4)	C15—H15B	0.9600
C7—N1	1.420 (3)	C15—H15C	0.9600
C7—C15	1.493 (4)	N1—S1	1.667 (2)
C8—C9	1.421 (4)	O1—S1	1.411 (3)
C8—I1	2.050 (3)	O2—S1	1.416 (3)
C6—C1—C2	121.9 (3)	C9—C10—H10	120.7
C6—C1—S1	119.1 (2)	C10—C11—C12	121.0 (3)
C2—C1—S1	119.0 (2)	C10—C11—H11	119.5
C1—C2—C3	118.5 (4)	C12—C11—H11	119.5
C1—C2—H2	120.8	C11—C12—C13	122.0 (3)
C3—C2—H2	120.8	C11—C12—H12	119.0
C4—C3—C2	120.0 (4)	C13—C12—H12	119.0
C4—C3—H3	120.0	C12—C13—C14	117.2 (3)
C2—C3—H3	120.0	C12—C13—H13	121.4
C3—C4—C5	121.1 (3)	C14—C13—H13	121.4
C3—C4—H4	119.4	C13—C14—C9	121.0 (2)
C5—C4—H4	119.4	C13—C14—N1	132.0 (3)
C4—C5—C6	119.9 (4)	C9—C14—N1	107.0 (2)
C4—C5—H5	120.0	C7—C15—H15A	109.5
C6—C5—H5	120.0	C7—C15—H15B	109.5
C1—C6—C5	118.6 (3)	H15A—C15—H15B	109.5
C1—C6—H6	120.7	C7—C15—H15C	109.5
C5—C6—H6	120.7	H15A—C15—H15C	109.5
C8—C7—N1	106.9 (2)	H15B—C15—H15C	109.5
C8—C7—C15	129.1 (3)	C14—N1—C7	108.7 (2)
N1—C7—C15	123.9 (3)	C14—N1—S1	125.89 (19)
C7—C8—C9	110.2 (2)	C7—N1—S1	124.72 (18)
C7—C8—I1	125.8 (2)	O1—S1—O2	120.43 (16)
C9—C8—I1	124.00 (18)	O1—S1—N1	105.47 (13)
C14—C9—C10	120.1 (2)	O2—S1—N1	107.93 (14)
C14—C9—C8	107.1 (2)	O1—S1—C1	109.09 (15)
C10—C9—C8	132.8 (3)	O2—S1—C1	107.83 (14)
C11—C10—C9	118.7 (3)	N1—S1—C1	105.06 (12)
C11—C10—H10	120.7
C6—C1—C2—C3	−0.7 (5)	C8—C9—C14—C13	−179.2 (3)
S1—C1—C2—C3	−178.7 (3)	C10—C9—C14—N1	−177.8 (2)
C1—C2—C3—C4	0.7 (6)	C8—C9—C14—N1	1.6 (3)
C2—C3—C4—C5	0.3 (6)	C13—C14—N1—C7	179.0 (3)
C3—C4—C5—C6	−1.1 (6)	C9—C14—N1—C7	−2.0 (3)
C2—C1—C6—C5	−0.1 (5)	C13—C14—N1—S1	8.1 (4)
S1—C1—C6—C5	177.9 (2)	C9—C14—N1—S1	−172.91 (19)
C4—C5—C6—C1	1.0 (5)	C8—C7—N1—C14	1.6 (3)
N1—C7—C8—C9	−0.5 (3)	C15—C7—N1—C14	−179.7 (3)
C15—C7—C8—C9	−179.2 (3)	C8—C7—N1—S1	172.6 (2)
N1—C7—C8—I1	179.13 (18)	C15—C7—N1—S1	−8.7 (4)
C15—C7—C8—I1	0.5 (5)	C14—N1—S1—O1	−19.0 (3)
C7—C8—C9—C14	−0.7 (3)	C7—N1—S1—O1	171.5 (2)
I1—C8—C9—C14	179.62 (18)	C14—N1—S1—O2	−149.0 (2)
C7—C8—C9—C10	178.6 (3)	C7—N1—S1—O2	41.5 (3)
I1—C8—C9—C10	−1.1 (4)	C14—N1—S1—C1	96.2 (2)
C14—C9—C10—C11	−1.3 (4)	C7—N1—S1—C1	−73.3 (2)
C8—C9—C10—C11	179.5 (3)	C6—C1—S1—O1	−139.6 (2)
C9—C10—C11—C12	0.0 (5)	C2—C1—S1—O1	38.4 (3)
C10—C11—C12—C13	1.3 (5)	C6—C1—S1—O2	−7.2 (3)
C11—C12—C13—C14	−1.1 (5)	C2—C1—S1—O2	170.8 (3)
C12—C13—C14—C9	−0.2 (4)	C6—C1—S1—N1	107.7 (2)
C12—C13—C14—N1	178.7 (3)	C2—C1—S1—N1	−74.2 (3)
C10—C9—C14—C13	1.4 (4)

Cg3 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.29	2.871 (4)	120
C4—H4···Cg3i	0.93	2.65	3.517 (5)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.29	2.871 (4)	120
C4—H4⋯Cg3i	0.93	2.65	3.517 (5)	156

Symmetry code: (i) .