2-Methyl-1-phenyl-sulfonyl-1H-indole-3-carbaldehyde.

In the title compound, C(16)H(13)NO(3)S, the sulfonyl-bound phenyl ring forms a dihedral angle of 84.17 (6)° with the indole ring system. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure exhibits weak inter-molecular C-H⋯O hydrogen bonds and π-π inter-actions between the five- and six-membered rings of the indole group [centroid-centroid distance = 3.6871 (9) Å].

Related literature

For the biological activities of indole compounds, see: Chai et al. (2006 ▶); Singh et al. (2000 ▶); Andreani et al. (2001 ▶). For related structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶); Ramathilagam et al. (2011 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H13NO3S

M = 299.33

Monoclinic,

a = 11.6305 (5) Å

b = 8.4039 (4) Å

c = 14.3128 (8) Å

β = 93.126 (1)°

V = 1396.87 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 295 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.949, T max = 0.958

18442 measured reflections

4242 independent reflections

3212 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.116

S = 1.06

4242 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.27 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 datablock(s) global, I. DOI: 10.1107/S1600536811035665/ci5199sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035665/ci5199Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035665/ci5199Isup3.cml

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

C16H13NO3S	F(000) = 624
Mr = 299.33	Dx = 1.423 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2Ybc	Cell parameters from 4242 reflections
a = 11.6305 (5) Å	θ = 2.8–30.5°
b = 8.4039 (4) Å	µ = 0.24 mm−1
c = 14.3128 (8) Å	T = 295 K
β = 93.126 (1)°	Block, colourless
V = 1396.87 (12) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4242 independent reflections
Radiation source: fine-focus sealed tube	3212 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω and φ scans	θmax = 30.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→16
Tmin = 0.949, Tmax = 0.958	k = −11→11
18442 measured reflections	l = −20→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.051P)2 + 0.3293P] where P = (Fo2 + 2Fc2)/3
4242 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	0.51033 (11)	1.03657 (16)	0.11957 (9)	0.0372 (3)
C2	0.62740 (13)	1.0134 (2)	0.14228 (11)	0.0488 (3)
H2	0.6794	1.0968	0.1382	0.059*
C3	0.66431 (13)	0.8654 (2)	0.17072 (12)	0.0541 (4)
H3	0.7420	0.8486	0.1863	0.065*
C4	0.58737 (14)	0.7403 (2)	0.17652 (11)	0.0509 (4)
H4	0.6148	0.6412	0.1961	0.061*
C5	0.47145 (13)	0.75842 (17)	0.15415 (10)	0.0442 (3)
H5	0.4203	0.6739	0.1581	0.053*
C6	0.43434 (11)	0.90840 (16)	0.12546 (9)	0.0356 (3)
C7	0.33085 (13)	1.12984 (17)	0.07792 (10)	0.0429 (3)
C8	0.44359 (12)	1.17348 (17)	0.08955 (9)	0.0412 (3)
C9	0.22868 (16)	1.2312 (2)	0.05301 (14)	0.0655 (5)
H9A	0.2527	1.3399	0.0472	0.098*
H9B	0.1747	1.2233	0.1012	0.098*
H9C	0.1929	1.1958	−0.0053	0.098*
C10	0.48781 (17)	1.3321 (2)	0.07368 (12)	0.0559 (4)
H10	0.4355	1.4109	0.0545	0.067*
C11	0.13200 (11)	0.92243 (17)	0.19354 (9)	0.0395 (3)
C12	0.18938 (12)	0.90248 (19)	0.27999 (10)	0.0457 (3)
H12	0.2640	0.8624	0.2845	0.055*
C13	0.13415 (16)	0.9431 (2)	0.35933 (11)	0.0569 (4)
H13	0.1717	0.9313	0.4180	0.068*
C14	0.02338 (16)	1.0010 (2)	0.35188 (13)	0.0624 (4)
H14	−0.0138	1.0270	0.4058	0.075*
C15	−0.03304 (14)	1.0211 (2)	0.26584 (13)	0.0613 (4)
H15	−0.1078	1.0608	0.2618	0.074*
C16	0.02108 (12)	0.9824 (2)	0.18524 (11)	0.0516 (4)
H16	−0.0163	0.9964	0.1267	0.062*
N1	0.32271 (9)	0.96653 (14)	0.09734 (8)	0.0411 (3)
O1	0.23308 (10)	0.69878 (14)	0.10309 (9)	0.0575 (3)
O2	0.13304 (10)	0.91043 (19)	0.01249 (8)	0.0667 (4)
O3	0.58819 (13)	1.36833 (15)	0.08380 (10)	0.0742 (4)
S1	0.20015 (3)	0.86138 (5)	0.09314 (2)	0.04468 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0448 (6)	0.0379 (7)	0.0289 (6)	−0.0030 (5)	0.0030 (5)	−0.0032 (5)
C2	0.0440 (7)	0.0547 (9)	0.0472 (8)	−0.0074 (6)	−0.0017 (6)	−0.0046 (7)
C3	0.0436 (7)	0.0656 (11)	0.0522 (9)	0.0079 (7)	−0.0060 (6)	−0.0027 (8)
C4	0.0571 (8)	0.0483 (9)	0.0471 (8)	0.0133 (7)	0.0004 (6)	0.0037 (7)
C5	0.0496 (7)	0.0387 (7)	0.0446 (7)	0.0006 (6)	0.0056 (6)	0.0048 (6)
C6	0.0385 (6)	0.0379 (7)	0.0307 (6)	0.0009 (5)	0.0045 (5)	0.0004 (5)
C7	0.0510 (7)	0.0415 (7)	0.0364 (7)	0.0070 (6)	0.0045 (6)	0.0049 (6)
C8	0.0537 (8)	0.0364 (7)	0.0336 (6)	−0.0022 (6)	0.0026 (5)	−0.0003 (5)
C9	0.0608 (10)	0.0607 (11)	0.0750 (12)	0.0181 (8)	0.0052 (9)	0.0158 (9)
C10	0.0760 (11)	0.0397 (8)	0.0511 (9)	−0.0074 (7)	−0.0044 (8)	0.0027 (7)
C11	0.0338 (6)	0.0439 (7)	0.0407 (7)	−0.0018 (5)	0.0020 (5)	0.0007 (6)
C12	0.0411 (7)	0.0510 (8)	0.0445 (8)	0.0027 (6)	−0.0011 (6)	0.0027 (6)
C13	0.0653 (10)	0.0651 (11)	0.0400 (8)	0.0036 (8)	0.0012 (7)	0.0007 (7)
C14	0.0630 (10)	0.0713 (12)	0.0545 (10)	0.0056 (9)	0.0169 (8)	−0.0067 (9)
C15	0.0439 (8)	0.0717 (12)	0.0690 (11)	0.0132 (8)	0.0091 (7)	−0.0060 (9)
C16	0.0385 (7)	0.0648 (10)	0.0508 (8)	0.0050 (6)	−0.0042 (6)	0.0012 (7)
N1	0.0372 (5)	0.0421 (7)	0.0442 (6)	−0.0003 (4)	0.0050 (4)	0.0063 (5)
O1	0.0532 (6)	0.0470 (6)	0.0737 (8)	−0.0101 (5)	0.0156 (5)	−0.0129 (6)
O2	0.0536 (6)	0.1042 (11)	0.0411 (6)	−0.0050 (7)	−0.0075 (5)	−0.0038 (6)
O3	0.0809 (9)	0.0546 (8)	0.0847 (10)	−0.0268 (7)	−0.0179 (7)	0.0078 (7)
S1	0.03861 (17)	0.0548 (2)	0.0407 (2)	−0.00535 (14)	0.00263 (13)	−0.00445 (15)

C1—C2	1.3962 (19)	C9—H9C	0.96
C1—C6	1.3988 (18)	C10—O3	1.207 (2)
C1—C8	1.4404 (19)	C10—H10	0.93
C2—C3	1.370 (2)	C11—C12	1.3835 (19)
C2—H2	0.93	C11—C16	1.3841 (19)
C3—C4	1.386 (2)	C11—S1	1.7552 (14)
C3—H3	0.93	C12—C13	1.378 (2)
C4—C5	1.377 (2)	C12—H12	0.93
C4—H4	0.93	C13—C14	1.376 (2)
C5—C6	1.3871 (19)	C13—H13	0.93
C5—H5	0.93	C14—C15	1.374 (3)
C6—N1	1.4246 (16)	C14—H14	0.93
C7—C8	1.363 (2)	C15—C16	1.383 (2)
C7—N1	1.4046 (19)	C15—H15	0.93
C7—C9	1.490 (2)	C16—H16	0.93
C8—C10	1.451 (2)	N1—S1	1.6753 (12)
C9—H9A	0.96	O1—S1	1.4242 (13)
C9—H9B	0.96	O2—S1	1.4190 (12)
C2—C1—C6	119.32 (13)	O3—C10—C8	124.15 (17)
C2—C1—C8	133.15 (13)	O3—C10—H10	117.9
C6—C1—C8	107.53 (12)	C8—C10—H10	117.9
C3—C2—C1	118.80 (14)	C12—C11—C16	121.52 (13)
C3—C2—H2	120.6	C12—C11—S1	118.64 (10)
C1—C2—H2	120.6	C16—C11—S1	119.77 (11)
C2—C3—C4	120.88 (14)	C13—C12—C11	118.90 (14)
C2—C3—H3	119.6	C13—C12—H12	120.6
C4—C3—H3	119.6	C11—C12—H12	120.6
C5—C4—C3	121.96 (15)	C14—C13—C12	120.02 (15)
C5—C4—H4	119.0	C14—C13—H13	120.0
C3—C4—H4	119.0	C12—C13—H13	120.0
C4—C5—C6	117.02 (14)	C15—C14—C13	120.82 (15)
C4—C5—H5	121.5	C15—C14—H14	119.6
C6—C5—H5	121.5	C13—C14—H14	119.6
C5—C6—C1	122.02 (12)	C14—C15—C16	120.14 (15)
C5—C6—N1	131.25 (12)	C14—C15—H15	119.9
C1—C6—N1	106.74 (12)	C16—C15—H15	119.9
C8—C7—N1	108.28 (12)	C15—C16—C11	118.59 (14)
C8—C7—C9	128.68 (14)	C15—C16—H16	120.7
N1—C7—C9	123.01 (14)	C11—C16—H16	120.7
C7—C8—C1	108.71 (12)	C7—N1—C6	108.71 (11)
C7—C8—C10	125.09 (14)	C7—N1—S1	125.08 (10)
C1—C8—C10	126.20 (14)	C6—N1—S1	126.14 (10)
C7—C9—H9A	109.5	O2—S1—O1	119.54 (8)
C7—C9—H9B	109.5	O2—S1—N1	107.77 (7)
H9A—C9—H9B	109.5	O1—S1—N1	106.19 (6)
C7—C9—H9C	109.5	O2—S1—C11	109.16 (7)
H9A—C9—H9C	109.5	O1—S1—C11	109.24 (7)
H9B—C9—H9C	109.5	N1—S1—C11	103.76 (6)
C6—C1—C2—C3	−0.7 (2)	C13—C14—C15—C16	0.2 (3)
C8—C1—C2—C3	178.78 (15)	C14—C15—C16—C11	0.5 (3)
C1—C2—C3—C4	0.3 (2)	C12—C11—C16—C15	−0.7 (2)
C2—C3—C4—C5	0.1 (2)	S1—C11—C16—C15	176.34 (13)
C3—C4—C5—C6	−0.1 (2)	C8—C7—N1—C6	2.23 (15)
C4—C5—C6—C1	−0.2 (2)	C9—C7—N1—C6	−175.57 (14)
C4—C5—C6—N1	179.63 (14)	C8—C7—N1—S1	179.33 (10)
C2—C1—C6—C5	0.6 (2)	C9—C7—N1—S1	1.5 (2)
C8—C1—C6—C5	−178.94 (12)	C5—C6—N1—C7	178.03 (14)
C2—C1—C6—N1	−179.26 (12)	C1—C6—N1—C7	−2.08 (14)
C8—C1—C6—N1	1.17 (14)	C5—C6—N1—S1	1.0 (2)
N1—C7—C8—C1	−1.48 (16)	C1—C6—N1—S1	−179.15 (9)
C9—C7—C8—C1	176.15 (15)	C7—N1—S1—O2	41.89 (14)
N1—C7—C8—C10	178.30 (13)	C6—N1—S1—O2	−141.51 (11)
C9—C7—C8—C10	−4.1 (3)	C7—N1—S1—O1	171.10 (11)
C2—C1—C8—C7	−179.31 (15)	C6—N1—S1—O1	−12.30 (13)
C6—C1—C8—C7	0.18 (15)	C7—N1—S1—C11	−73.79 (13)
C2—C1—C8—C10	0.9 (2)	C6—N1—S1—C11	102.82 (12)
C6—C1—C8—C10	−179.60 (13)	C12—C11—S1—O2	−172.81 (12)
C7—C8—C10—O3	−179.51 (16)	C16—C11—S1—O2	10.03 (16)
C1—C8—C10—O3	0.2 (3)	C12—C11—S1—O1	54.80 (13)
C16—C11—C12—C13	0.2 (2)	C16—C11—S1—O1	−122.36 (13)
S1—C11—C12—C13	−176.90 (13)	C12—C11—S1—N1	−58.13 (13)
C11—C12—C13—C14	0.6 (3)	C16—C11—S1—N1	124.72 (13)
C12—C13—C14—C15	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.28	2.8723 (19)	121
C12—H12···O3i	0.93	2.48	3.1664 (19)	131
C16—H16···O2ii	0.93	2.48	3.388 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1	0.93	2.28	2.8723 (19)	121
C12—H12⋯O3i	0.93	2.48	3.1664 (19)	131
C16—H16⋯O2ii	0.93	2.48	3.388 (2)	167

Symmetry codes: (i) ; (ii) .