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

In the title compound, C(16)H(14)ClNO(2)S, the phenyl ring makes a dihedral angle of 78.1 (1)° with the indole ring system. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions. The crystal structure exhibits weak inter-molecular C-H⋯O, C-H⋯π and π-π [centroid-centroid distances = 3.620 (1)-3.794 (1) Å] inter-actions.

Related literature

For the biological activity of indole derivatives, see: Okabe & Adachi (1998 ▶); Schollmeyer et al. (1995 ▶). For related crystal structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C16H14ClNO2S

M = 319.79

Monoclinic,

a = 7.9769 (6) Å

b = 10.8064 (9) Å

c = 17.3418 (12) Å

β = 97.500 (2)°

V = 1482.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 295 K

0.30 × 0.28 × 0.26 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.889, T max = 0.903

17616 measured reflections

3885 independent reflections

3201 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.120

S = 1.04

3885 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.45 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 global, I. DOI: 10.1107/S1600536809041191/is2470sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041191/is2470Isup2.hkl

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

C16H14ClNO2S	F(000) = 664
Mr = 319.79	Dx = 1.433 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8432 reflections
a = 7.9769 (6) Å	θ = 2.2–28.8°
b = 10.8064 (9) Å	µ = 0.40 mm−1
c = 17.3418 (12) Å	T = 295 K
β = 97.500 (2)°	Block, colourless
V = 1482.1 (2) Å3	0.30 × 0.28 × 0.26 mm
Z = 4

Bruker Kappa APEXII diffractometer	3885 independent reflections
Radiation source: fine-focus sealed tube	3201 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω and φ scans	θmax = 28.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.889, Tmax = 0.903	k = −14→14
17616 measured reflections	l = −13→23

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) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0606P)2 + 0.5623P] where P = (Fo2 + 2Fc2)/3
3885 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.2222 (2)	0.12567 (15)	0.26775 (9)	0.0376 (3)
C2	0.2156 (3)	0.03299 (18)	0.21251 (11)	0.0510 (4)
H2	0.1172	−0.0125	0.1989	0.061*
C3	0.3596 (3)	0.0096 (2)	0.17795 (12)	0.0633 (6)
H3	0.3576	−0.0519	0.1403	0.076*
C4	0.5042 (3)	0.0757 (2)	0.19847 (13)	0.0602 (5)
H4	0.6006	0.0573	0.1758	0.072*
C5	0.5086 (3)	0.1686 (2)	0.25200 (12)	0.0554 (5)
H5	0.6069	0.2145	0.2647	0.067*
C6	0.3671 (2)	0.19466 (18)	0.28736 (10)	0.0460 (4)
H6	0.3695	0.2578	0.3239	0.055*
C7	0.1768 (2)	0.16719 (15)	0.47207 (10)	0.0391 (3)
C8	0.2587 (2)	0.08731 (16)	0.52391 (9)	0.0408 (4)
C9	0.2430 (2)	−0.03433 (15)	0.49110 (9)	0.0371 (3)
C10	0.3019 (3)	−0.14938 (18)	0.51880 (11)	0.0498 (4)
H10	0.3646	−0.1568	0.5677	0.060*
C11	0.2658 (3)	−0.25159 (18)	0.47269 (13)	0.0543 (5)
H11	0.3054	−0.3288	0.4904	0.065*
C12	0.1713 (3)	−0.24139 (17)	0.40010 (12)	0.0503 (4)
H12	0.1491	−0.3121	0.3700	0.060*
C13	0.1090 (2)	−0.12916 (16)	0.37131 (10)	0.0426 (4)
H13	0.0446	−0.1229	0.3227	0.051*
C14	0.14676 (19)	−0.02597 (15)	0.41808 (9)	0.0343 (3)
C15	0.1467 (3)	0.29996 (17)	0.48501 (12)	0.0530 (5)
H15A	0.1376	0.3130	0.5396	0.064*
H15B	0.0398	0.3236	0.4555	0.064*
C16	0.3463 (3)	0.1166 (2)	0.60340 (11)	0.0604 (5)
H16A	0.3348	0.2033	0.6137	0.091*
H16B	0.4640	0.0960	0.6062	0.091*
H16C	0.2963	0.0694	0.6414	0.091*
N1	0.10231 (17)	0.09922 (13)	0.40560 (7)	0.0370 (3)
O1	−0.08880 (16)	0.07654 (16)	0.28192 (8)	0.0602 (4)
O2	0.0208 (2)	0.28227 (14)	0.32369 (9)	0.0621 (4)
S1	0.04580 (5)	0.15288 (4)	0.31625 (2)	0.04245 (13)
Cl1	0.31210 (9)	0.39887 (5)	0.45712 (4)	0.07026 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0415 (8)	0.0392 (8)	0.0318 (7)	0.0045 (6)	0.0032 (6)	0.0087 (6)
C2	0.0614 (11)	0.0464 (10)	0.0462 (9)	−0.0100 (9)	0.0108 (8)	−0.0018 (8)
C3	0.0900 (16)	0.0496 (12)	0.0557 (12)	−0.0003 (11)	0.0294 (11)	−0.0080 (9)
C4	0.0614 (12)	0.0649 (13)	0.0592 (12)	0.0082 (10)	0.0270 (10)	0.0068 (10)
C5	0.0454 (9)	0.0698 (14)	0.0519 (10)	−0.0043 (9)	0.0090 (8)	0.0039 (9)
C6	0.0467 (9)	0.0519 (10)	0.0389 (8)	−0.0010 (8)	0.0040 (7)	−0.0004 (7)
C7	0.0465 (9)	0.0336 (8)	0.0401 (8)	−0.0044 (7)	0.0162 (7)	−0.0023 (6)
C8	0.0469 (9)	0.0415 (9)	0.0347 (7)	−0.0092 (7)	0.0082 (6)	−0.0005 (6)
C9	0.0391 (8)	0.0374 (8)	0.0349 (7)	−0.0027 (6)	0.0058 (6)	0.0039 (6)
C10	0.0539 (10)	0.0460 (10)	0.0470 (9)	0.0006 (8)	−0.0025 (8)	0.0117 (8)
C11	0.0630 (12)	0.0355 (9)	0.0649 (12)	0.0069 (8)	0.0097 (9)	0.0094 (8)
C12	0.0585 (11)	0.0359 (9)	0.0579 (11)	−0.0027 (8)	0.0130 (9)	−0.0072 (8)
C13	0.0474 (9)	0.0413 (9)	0.0392 (8)	−0.0026 (7)	0.0057 (7)	−0.0033 (7)
C14	0.0355 (7)	0.0338 (8)	0.0344 (7)	0.0006 (6)	0.0081 (6)	0.0029 (6)
C15	0.0683 (12)	0.0373 (9)	0.0588 (11)	−0.0017 (9)	0.0279 (9)	−0.0040 (8)
C16	0.0773 (14)	0.0624 (13)	0.0397 (9)	−0.0185 (11)	0.0007 (9)	−0.0052 (9)
N1	0.0423 (7)	0.0337 (7)	0.0354 (6)	0.0033 (5)	0.0070 (5)	0.0039 (5)
O1	0.0372 (6)	0.0834 (11)	0.0567 (8)	0.0000 (7)	−0.0064 (6)	0.0106 (7)
O2	0.0714 (10)	0.0515 (9)	0.0644 (9)	0.0286 (7)	0.0124 (7)	0.0183 (7)
S1	0.0366 (2)	0.0485 (3)	0.0416 (2)	0.01086 (17)	0.00270 (15)	0.01142 (17)
Cl1	0.0967 (4)	0.0386 (3)	0.0815 (4)	−0.0169 (3)	0.0344 (3)	−0.0031 (2)

C1—C6	1.380 (3)	C10—C11	1.372 (3)
C1—C2	1.382 (3)	C10—H10	0.9300
C1—S1	1.7559 (17)	C11—C12	1.385 (3)
C2—C3	1.387 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.379 (3)
C3—C4	1.364 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.389 (2)
C4—C5	1.365 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—N1	1.408 (2)
C5—C6	1.382 (3)	C15—Cl1	1.812 (2)
C5—H5	0.9300	C15—H15A	0.9700
C6—H6	0.9300	C15—H15B	0.9700
C7—C8	1.352 (2)	C16—H16A	0.9600
C7—N1	1.429 (2)	C16—H16B	0.9600
C7—C15	1.477 (2)	C16—H16C	0.9600
C8—C9	1.431 (2)	N1—S1	1.6607 (13)
C8—C16	1.496 (2)	O1—S1	1.4216 (15)
C9—C10	1.392 (2)	O2—S1	1.4206 (15)
C9—C14	1.395 (2)
C6—C1—C2	121.15 (17)	C12—C11—H11	119.5
C6—C1—S1	119.29 (13)	C13—C12—C11	121.79 (18)
C2—C1—S1	119.53 (14)	C13—C12—H12	119.1
C1—C2—C3	118.21 (19)	C11—C12—H12	119.1
C1—C2—H2	120.9	C12—C13—C14	117.02 (17)
C3—C2—H2	120.9	C12—C13—H13	121.5
C4—C3—C2	120.80 (19)	C14—C13—H13	121.5
C4—C3—H3	119.6	C13—C14—C9	121.98 (15)
C2—C3—H3	119.6	C13—C14—N1	130.59 (15)
C3—C4—C5	120.56 (19)	C9—C14—N1	107.42 (13)
C3—C4—H4	119.7	C7—C15—Cl1	113.22 (13)
C5—C4—H4	119.7	C7—C15—H15A	108.9
C4—C5—C6	120.1 (2)	Cl1—C15—H15A	108.9
C4—C5—H5	119.9	C7—C15—H15B	108.9
C6—C5—H5	119.9	Cl1—C15—H15B	108.9
C1—C6—C5	119.14 (18)	H15A—C15—H15B	107.7
C1—C6—H6	120.4	C8—C16—H16A	109.5
C5—C6—H6	120.4	C8—C16—H16B	109.5
C8—C7—N1	108.80 (14)	H16A—C16—H16B	109.5
C8—C7—C15	126.40 (17)	C8—C16—H16C	109.5
N1—C7—C15	124.29 (16)	H16A—C16—H16C	109.5
C7—C8—C9	108.21 (15)	H16B—C16—H16C	109.5
C7—C8—C16	127.22 (17)	C14—N1—C7	107.46 (13)
C9—C8—C16	124.53 (17)	C14—N1—S1	120.74 (11)
C10—C9—C14	119.47 (16)	C7—N1—S1	127.36 (12)
C10—C9—C8	132.44 (16)	O2—S1—O1	120.13 (10)
C14—C9—C8	108.08 (14)	O2—S1—N1	106.45 (8)
C11—C10—C9	118.82 (17)	O1—S1—N1	106.64 (8)
C11—C10—H10	120.6	O2—S1—C1	109.81 (9)
C9—C10—H10	120.6	O1—S1—C1	108.11 (9)
C10—C11—C12	120.91 (18)	N1—S1—C1	104.57 (7)
C10—C11—H11	119.5
C6—C1—C2—C3	1.0 (3)	C10—C9—C14—N1	179.02 (15)
S1—C1—C2—C3	−176.87 (15)	C8—C9—C14—N1	−0.22 (18)
C1—C2—C3—C4	0.5 (3)	C8—C7—C15—Cl1	91.1 (2)
C2—C3—C4—C5	−1.8 (4)	N1—C7—C15—Cl1	−98.03 (19)
C3—C4—C5—C6	1.6 (3)	C13—C14—N1—C7	−179.07 (16)
C2—C1—C6—C5	−1.2 (3)	C9—C14—N1—C7	1.18 (17)
S1—C1—C6—C5	176.64 (15)	C13—C14—N1—S1	−21.1 (2)
C4—C5—C6—C1	−0.1 (3)	C9—C14—N1—S1	159.16 (11)
N1—C7—C8—C9	1.60 (19)	C8—C7—N1—C14	−1.75 (17)
C15—C7—C8—C9	173.60 (16)	C15—C7—N1—C14	−173.96 (15)
N1—C7—C8—C16	−176.32 (18)	C8—C7—N1—S1	−157.84 (13)
C15—C7—C8—C16	−4.3 (3)	C15—C7—N1—S1	30.0 (2)
C7—C8—C9—C10	−179.98 (19)	C14—N1—S1—O2	−176.12 (13)
C16—C8—C9—C10	−2.0 (3)	C7—N1—S1—O2	−22.86 (16)
C7—C8—C9—C14	−0.87 (19)	C14—N1—S1—O1	54.50 (14)
C16—C8—C9—C14	177.12 (17)	C7—N1—S1—O1	−152.24 (14)
C14—C9—C10—C11	1.1 (3)	C14—N1—S1—C1	−59.89 (14)
C8—C9—C10—C11	−179.89 (19)	C7—N1—S1—C1	93.37 (15)
C9—C10—C11—C12	−0.6 (3)	C6—C1—S1—O2	43.32 (16)
C10—C11—C12—C13	−0.3 (3)	C2—C1—S1—O2	−138.81 (15)
C11—C12—C13—C14	0.6 (3)	C6—C1—S1—O1	176.10 (14)
C12—C13—C14—C9	−0.1 (2)	C2—C1—S1—O1	−6.02 (17)
C12—C13—C14—N1	−179.82 (17)	C6—C1—S1—N1	−70.55 (15)
C10—C9—C14—C13	−0.8 (2)	C2—C1—S1—N1	107.33 (15)
C8—C9—C14—C13	180.00 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.51	2.886 (3)	104
C13—H13···O1	0.93	2.47	3.033 (2)	119
C15—H15B···O2	0.97	2.31	2.853 (3)	114
C2—H2···O2i	0.93	2.48	3.314 (2)	149
C16—H16A···Cg2ii	0.96	2.94	3.777 (2)	146
C16—H16B···Cg3iii	0.96	2.92	3.781 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.51	2.886 (3)	104
C13—H13⋯O1	0.93	2.47	3.033 (2)	119
C15—H15B⋯O2	0.97	2.31	2.853 (3)	114
C16—H16A⋯Cg2ii	0.96	2.94	3.777 (2)	146
C16—H16B⋯Cg3iii	0.96	2.92	3.781 (3)	149

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 and Cg3 are the centroids of the C1–C6 and C9–C14 rings, respectively.