3-Bromo-meth-yl-2-chloro-meth-yl-1-phenyl-sulfon-yl-1H-indole.

In the title compound, C(16)H(13)BrClNO(2)S, the indole mean plane forms a dihedral angle of 73.59 (19)° with the phenyl ring. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions. The Br atom is disordered over two positions with site occupancy factors of 0.7 and 0.3.

Related literature

For related crystal structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶). For the biological activities of indole derivatives, see: Chai et al. (2006 ▶); Nieto et al. (2005 ▶); Olgen & Coban (2003 ▶).

Experimental

Crystal data

C16H13BrClNO2S

M = 398.69

Monoclinic,

a = 11.8501 (9) Å

b = 16.3525 (13) Å

c = 8.5793 (6) Å

β = 108.766 (3)°

V = 1574.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.92 mm−1

T = 295 (2) K

0.16 × 0.14 × 0.14 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.559, T max = 0.665

14367 measured reflections

2770 independent reflections

1822 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.231

S = 1.06

2770 reflections

209 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.92 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/S1600536808007678/bt2689sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007678/bt2689Isup2.hkl

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

C16H13BrClNO2S	F000 = 800
Mr = 398.69	Dx = 1.682 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4037 reflections
a = 11.8501 (9) Å	θ = 2.5–25.0º
b = 16.3525 (13) Å	µ = 2.92 mm−1
c = 8.5793 (6) Å	T = 295 (2) K
β = 108.766 (3)º	Block, colourless
V = 1574.1 (2) Å3	0.16 × 0.14 × 0.14 mm
Z = 4

Bruker Kappa APEXII diffractometer	2770 independent reflections
Radiation source: fine-focus sealed tube	1822 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
T = 295(2) K	θmax = 25.0º
ω and φ scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −14→13
Tmin = 0.559, Tmax = 0.665	k = −19→19
14367 measured reflections	l = −10→10

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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.231	w = 1/[σ2(Fo2) + (0.127P)2 + 1.9456P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2770 reflections	Δρmax = 0.42 e Å−3
209 parameters	Δρmin = −0.91 e Å−3
12 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.90925 (16)	−0.10531 (12)	0.5085 (3)	0.0872 (6)
Br1	0.8135 (6)	0.1043 (5)	0.3205 (5)	0.1572 (16)	0.709 (16)
Br1A	0.7901 (4)	0.1251 (3)	0.3139 (9)	0.093 (2)	0.291 (16)
S1	0.70049 (14)	−0.13649 (11)	0.8192 (2)	0.0743 (6)
O1	0.6340 (5)	−0.1191 (4)	0.9258 (8)	0.114 (2)
O2	0.6743 (5)	−0.2077 (3)	0.7212 (8)	0.109 (2)
N1	0.6795 (4)	−0.0573 (3)	0.6922 (5)	0.0539 (11)
C1	0.8512 (6)	−0.1369 (4)	0.9320 (7)	0.0655 (17)
C2	0.8952 (7)	−0.0826 (5)	1.0604 (8)	0.097 (2)
H2	0.8449	−0.0449	1.0854	0.117*
C3	1.0161 (8)	−0.0849 (8)	1.1523 (11)	0.127 (4)
H3	1.0474	−0.0485	1.2387	0.153*
C4	1.0885 (9)	−0.1418 (7)	1.1133 (13)	0.122 (4)
H4	1.1688	−0.1441	1.1753	0.147*
C5	1.0442 (8)	−0.1951 (6)	0.9845 (13)	0.113 (3)
H5	1.0947	−0.2325	0.9590	0.135*
C6	0.9256 (7)	−0.1932 (5)	0.8934 (10)	0.086 (2)
H6	0.8953	−0.2295	0.8065	0.103*
C7	0.7000 (5)	−0.0556 (3)	0.5384 (7)	0.0574 (14)
C8	0.6681 (5)	0.0197 (3)	0.4715 (6)	0.0535 (14)
C9	0.6288 (5)	0.0680 (3)	0.5809 (5)	0.0463 (12)
C10	0.5887 (6)	0.1477 (4)	0.5707 (7)	0.0622 (15)
H10	0.5837	0.1796	0.4790	0.075*
C11	0.5563 (6)	0.1790 (4)	0.6984 (8)	0.078 (2)
H11	0.5295	0.2327	0.6939	0.094*
C12	0.5633 (7)	0.1313 (5)	0.8332 (9)	0.083 (2)
H12	0.5406	0.1537	0.9182	0.099*
C13	0.6026 (6)	0.0519 (5)	0.8471 (6)	0.0687 (18)
H13	0.6064	0.0203	0.9388	0.082*
C14	0.6365 (4)	0.0206 (3)	0.7184 (6)	0.0468 (12)
C15	0.7557 (4)	−0.1232 (4)	0.4743 (11)	0.086 (2)
H15A	0.7151	−0.1294	0.3572	0.103*
H15B	0.7464	−0.1739	0.5278	0.103*
C16	0.6722 (5)	0.0443 (4)	0.3064 (7)	0.084 (2)
H16A	0.6030	0.0777	0.2520	0.101*	0.709 (16)
H16B	0.6686	−0.0042	0.2400	0.101*	0.709 (16)
H16C	0.6052	0.0802	0.2560	0.101*	0.291 (16)
H16D	0.6645	−0.0033	0.2363	0.101*	0.291 (16)

	U11	U22	U33	U12	U13	U23
Cl1	0.0663 (11)	0.0872 (13)	0.1176 (15)	0.0181 (9)	0.0429 (10)	−0.0109 (10)
Br1	0.235 (3)	0.159 (3)	0.106 (2)	−0.112 (2)	0.095 (2)	−0.0245 (15)
Br1A	0.063 (4)	0.105 (3)	0.098 (3)	−0.014 (2)	0.008 (2)	0.041 (3)
S1	0.0540 (9)	0.0688 (11)	0.0926 (12)	−0.0071 (8)	0.0129 (8)	0.0402 (9)
O1	0.082 (3)	0.142 (5)	0.130 (5)	0.015 (3)	0.053 (3)	0.087 (4)
O2	0.087 (3)	0.059 (3)	0.144 (5)	−0.029 (3)	−0.016 (3)	0.035 (3)
N1	0.057 (3)	0.049 (3)	0.052 (2)	0.000 (2)	0.012 (2)	0.013 (2)
C1	0.061 (4)	0.067 (4)	0.065 (4)	−0.010 (3)	0.015 (3)	0.028 (3)
C2	0.100 (6)	0.123 (7)	0.058 (4)	−0.002 (5)	0.010 (4)	0.011 (4)
C3	0.123 (8)	0.145 (10)	0.079 (6)	−0.039 (8)	−0.016 (6)	0.010 (6)
C4	0.077 (6)	0.138 (9)	0.121 (8)	−0.020 (6)	−0.010 (6)	0.051 (7)
C5	0.076 (6)	0.116 (7)	0.139 (8)	0.024 (5)	0.025 (6)	0.041 (7)
C6	0.072 (5)	0.077 (5)	0.096 (5)	0.011 (4)	0.009 (4)	0.019 (4)
C7	0.064 (4)	0.051 (3)	0.059 (3)	−0.005 (3)	0.023 (3)	−0.008 (3)
C8	0.070 (4)	0.053 (3)	0.039 (3)	−0.007 (3)	0.020 (2)	−0.002 (2)
C9	0.047 (3)	0.052 (3)	0.034 (2)	−0.002 (2)	0.005 (2)	−0.001 (2)
C10	0.066 (4)	0.050 (3)	0.061 (3)	0.006 (3)	0.007 (3)	0.005 (3)
C11	0.066 (4)	0.066 (4)	0.095 (5)	0.014 (3)	0.014 (4)	−0.021 (4)
C12	0.071 (4)	0.106 (6)	0.073 (4)	0.003 (4)	0.028 (4)	−0.036 (4)
C13	0.062 (4)	0.104 (5)	0.037 (3)	−0.001 (4)	0.013 (3)	−0.002 (3)
C14	0.043 (3)	0.057 (3)	0.038 (2)	−0.003 (2)	0.009 (2)	0.004 (2)
C15	0.079 (3)	0.074 (5)	0.110 (6)	−0.007 (4)	0.039 (4)	−0.026 (4)
C16	0.134 (5)	0.073 (4)	0.051 (3)	−0.026 (4)	0.038 (4)	0.001 (3)

Cl1—C15	1.772 (4)	C7—C8	1.359 (8)
Br1—C16	1.9114 (11)	C7—C15	1.481 (9)
Br1A—C16	1.9084 (11)	C8—C9	1.415 (8)
S1—O2	1.411 (6)	C8—C16	1.489 (7)
S1—O1	1.415 (6)	C9—C10	1.381 (8)
S1—N1	1.659 (4)	C9—C14	1.390 (7)
S1—C1	1.737 (6)	C10—C11	1.371 (7)
N1—C14	1.417 (7)	C10—H10	0.9300
N1—C7	1.417 (7)	C11—C12	1.375 (8)
C1—C2	1.380 (8)	C11—H11	0.9300
C1—C6	1.386 (10)	C12—C13	1.372 (10)
C2—C3	1.396 (8)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.387 (8)
C3—C4	1.379 (9)	C13—H13	0.9300
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.371 (9)	C15—H15B	0.9700
C4—H4	0.9300	C16—H16A	0.9700
C5—C6	1.371 (12)	C16—H16B	0.9700
C5—H5	0.9300	C16—H16C	0.9700
C6—H6	0.9300	C16—H16D	0.9700
O2—S1—O1	119.3 (4)	C9—C10—H10	120.6
O2—S1—N1	107.2 (3)	C10—C11—C12	120.3 (6)
O1—S1—N1	105.7 (3)	C10—C11—H11	119.9
O2—S1—C1	108.5 (3)	C12—C11—H11	119.9
O1—S1—C1	109.1 (4)	C13—C12—C11	122.5 (6)
N1—S1—C1	106.2 (3)	C13—C12—H12	118.8
C14—N1—C7	108.0 (4)	C11—C12—H12	118.8
C14—N1—S1	125.7 (4)	C12—C13—C14	117.1 (6)
C7—N1—S1	126.3 (4)	C12—C13—H13	121.4
C2—C1—C6	120.8 (7)	C14—C13—H13	121.4
C2—C1—S1	119.9 (6)	C13—C14—C9	120.9 (5)
C6—C1—S1	119.3 (5)	C13—C14—N1	131.9 (5)
C1—C2—C3	119.3 (8)	C9—C14—N1	107.2 (4)
C1—C2—H2	120.4	C7—C15—Cl1	111.8 (4)
C3—C2—H2	120.4	C7—C15—H15A	109.3
C4—C3—C2	119.1 (9)	Cl1—C15—H15A	109.3
C4—C3—H3	120.4	C7—C15—H15B	109.3
C2—C3—H3	120.4	Cl1—C15—H15B	109.3
C5—C4—C3	121.2 (9)	H15A—C15—H15B	107.9
C5—C4—H4	119.4	C8—C16—Br1A	113.8 (4)
C3—C4—H4	119.4	C8—C16—Br1	112.0 (4)
C6—C5—C4	120.1 (9)	C8—C16—H16A	109.2
C6—C5—H5	119.9	Br1A—C16—H16A	97.1
C4—C5—H5	119.9	Br1—C16—H16A	109.2
C5—C6—C1	119.5 (8)	C8—C16—H16B	109.2
C5—C6—H6	120.3	Br1A—C16—H16B	118.6
C1—C6—H6	120.3	Br1—C16—H16B	109.2
C8—C7—N1	107.6 (5)	H16A—C16—H16B	107.9
C8—C7—C15	128.1 (6)	C8—C16—H16C	108.4
N1—C7—C15	124.2 (6)	Br1A—C16—H16C	94.7
C7—C8—C9	109.4 (5)	Br1—C16—H16C	107.0
C7—C8—C16	123.8 (6)	H16B—C16—H16C	111.0
C9—C8—C16	126.7 (5)	C8—C16—H16D	110.3
C10—C9—C14	120.5 (5)	Br1A—C16—H16D	119.9
C10—C9—C8	131.7 (5)	Br1—C16—H16D	110.9
C14—C9—C8	107.8 (5)	H16A—C16—H16D	104.9
C11—C10—C9	118.7 (5)	H16C—C16—H16D	108.0
C11—C10—H10	120.6
O2—S1—N1—C14	146.0 (5)	C15—C7—C8—C16	7.1 (9)
O1—S1—N1—C14	17.8 (6)	C7—C8—C9—C10	179.3 (6)
C1—S1—N1—C14	−98.1 (5)	C16—C8—C9—C10	−2.1 (10)
O2—S1—N1—C7	−33.4 (6)	C7—C8—C9—C14	−0.3 (6)
O1—S1—N1—C7	−161.6 (5)	C16—C8—C9—C14	178.3 (5)
C1—S1—N1—C7	82.5 (5)	C14—C9—C10—C11	−0.2 (8)
O2—S1—C1—C2	−167.5 (6)	C8—C9—C10—C11	−179.8 (6)
O1—S1—C1—C2	−36.0 (6)	C9—C10—C11—C12	−0.4 (10)
N1—S1—C1—C2	77.6 (6)	C10—C11—C12—C13	0.3 (11)
O2—S1—C1—C6	11.3 (6)	C11—C12—C13—C14	0.4 (10)
O1—S1—C1—C6	142.8 (5)	C12—C13—C14—C9	−0.9 (8)
N1—S1—C1—C6	−103.7 (5)	C12—C13—C14—N1	−179.4 (6)
C6—C1—C2—C3	−0.2 (11)	C10—C9—C14—C13	0.9 (8)
S1—C1—C2—C3	178.6 (7)	C8—C9—C14—C13	−179.4 (5)
C1—C2—C3—C4	−0.5 (15)	C10—C9—C14—N1	179.7 (5)
C2—C3—C4—C5	1.1 (17)	C8—C9—C14—N1	−0.6 (6)
C3—C4—C5—C6	−1.0 (16)	C7—N1—C14—C13	179.9 (6)
C4—C5—C6—C1	0.3 (13)	S1—N1—C14—C13	0.4 (8)
C2—C1—C6—C5	0.2 (11)	C7—N1—C14—C9	1.3 (6)
S1—C1—C6—C5	−178.5 (6)	S1—N1—C14—C9	−178.2 (4)
C14—N1—C7—C8	−1.5 (6)	C8—C7—C15—Cl1	76.0 (8)
S1—N1—C7—C8	178.0 (4)	N1—C7—C15—Cl1	−98.7 (7)
C14—N1—C7—C15	174.1 (5)	C7—C8—C16—Br1A	−112.1 (6)
S1—N1—C7—C15	−6.4 (8)	C9—C8—C16—Br1A	69.5 (8)
N1—C7—C8—C9	1.1 (6)	C7—C8—C16—Br1	−98.2 (7)
C15—C7—C8—C9	−174.3 (5)	C9—C8—C16—Br1	83.4 (8)
N1—C7—C8—C16	−177.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.51	2.877 (9)	104
C13—H13···O1	0.93	2.31	2.873 (10)	118
C15—H15B···O2	0.97	2.17	2.939 (10)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2	0.93	2.51	2.877 (9)	104
C13—H13⋯O1	0.93	2.31	2.873 (10)	118
C15—H15B⋯O2	0.97	2.17	2.939 (10)	136