4-Bromo-meth-yl-1-phenyl-sulfon-yl-1H-indole.

In the title mol-ecule, C(15)H(12)BrNO(2)S, the indole mean plane and phenyl ring are nearly orthogonal to each other, forming a dihedral angle of 88.19 (13)°. The Br atom is disordered over two close positions with occupancies of 0.56 (4) and 0.44 (4). The crystal packing exhibits weak inter-molecular C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C15H12BrNO2S

M = 350.23

Monoclinic,

a = 11.7060 (9) Å

b = 8.2399 (7) Å

c = 15.4495 (11) Å

β = 103.858 (3)°

V = 1446.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.98 mm−1

T = 295 (2) K

0.18 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEX2 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.566, T max = 0.620

16472 measured reflections

3606 independent reflections

2160 reflections with I > 2s(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.199

S = 1.06

3606 reflections

191 parameters

8 restraints

H-atom parameters constrained

Δρmax = 1.25 e Å−3

Δρmin = −0.54 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/S1600536808007794/cv2392sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007794/cv2392Isup2.hkl

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

C15H12BrNO2S	F000 = 704
Mr = 350.23	Dx = 1.608 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5113 reflections
a = 11.7060 (9) Å	θ = 2.5–25.8º
b = 8.2399 (7) Å	µ = 2.99 mm−1
c = 15.4495 (11) Å	T = 295 (2) K
β = 103.858 (3)º	Block, colourless
V = 1446.8 (2) Å3	0.18 × 0.18 × 0.16 mm
Z = 4

Bruker Kappa APEX2 diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2160 reflections with I > 2s(I)
Monochromator: graphite	Rint = 0.041
T = 295(2) K	θmax = 28.6º
ω and φ scan	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.566, Tmax = 0.620	k = −10→11
16472 measured reflections	l = −12→20

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)] = 0.062	H-atom parameters constrained
wR(F2) = 0.199	w = 1/[σ2(Fo2) + (0.089P)2 + 1.9138P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3606 reflections	Δρmax = 1.25 e Å−3
191 parameters	Δρmin = −0.54 e Å−3
8 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.7826 (5)	0.6808 (6)	0.2167 (3)	0.0595 (13)
H1	0.8345	0.7022	0.1810	0.071*
C2	0.7274 (4)	0.7938 (6)	0.2531 (3)	0.0576 (12)
H2	0.7326	0.9055	0.2463	0.069*
C3	0.6578 (4)	0.7104 (6)	0.3052 (3)	0.0501 (11)
C4	0.5821 (4)	0.7671 (7)	0.3555 (3)	0.0605 (13)
C5	0.5258 (5)	0.6520 (8)	0.3953 (4)	0.0771 (18)
H5	0.4734	0.6856	0.4284	0.092*
C6	0.5457 (6)	0.4882 (9)	0.3870 (4)	0.0769 (18)
H6	0.5063	0.4147	0.4151	0.092*
C7	0.6223 (5)	0.4290 (7)	0.3385 (4)	0.0643 (14)
H7	0.6367	0.3186	0.3345	0.077*
C8	0.6757 (4)	0.5440 (6)	0.2967 (3)	0.0489 (11)
C10	0.9404 (4)	0.3588 (5)	0.3317 (3)	0.0502 (11)
C11	0.9363 (5)	0.2442 (6)	0.3965 (3)	0.0673 (14)
H11	0.8754	0.1690	0.3884	0.081*
C12	1.0253 (5)	0.2450 (8)	0.4736 (3)	0.0833 (19)
H12	1.0248	0.1697	0.5183	0.100*
C13	1.1153 (5)	0.3580 (7)	0.4842 (4)	0.0805 (19)
H13	1.1751	0.3569	0.5361	0.097*
C14	1.1177 (5)	0.4719 (7)	0.4194 (3)	0.0765 (17)
H14	1.1783	0.5477	0.4277	0.092*
C15	1.0293 (4)	0.4726 (6)	0.3419 (3)	0.0621 (13)
H15	1.0297	0.5484	0.2973	0.075*
N1	0.7516 (3)	0.5255 (5)	0.2396 (3)	0.0524 (10)
O1	0.8833 (4)	0.3941 (6)	0.1596 (2)	0.0771 (12)
O2	0.7575 (3)	0.2269 (5)	0.2295 (3)	0.0775 (11)
S1	0.83141 (11)	0.36176 (16)	0.23203 (8)	0.0569 (4)
C9	0.5669 (4)	0.9457 (7)	0.3700 (3)	0.0725 (16)
H9A	0.4865	0.9665	0.3734	0.087*	0.56 (4)
H9B	0.5813	1.0060	0.3198	0.087*	0.56 (4)
H9C	0.4898	0.9633	0.3813	0.087*	0.44 (4)
H9D	0.5701	1.0035	0.3160	0.087*	0.44 (4)
Br1	0.6721 (4)	1.0180 (7)	0.4768 (3)	0.0792 (10)	0.56 (4)
Br1A	0.6841 (7)	1.0268 (5)	0.4688 (5)	0.0844 (16)	0.44 (4)

	U11	U22	U33	U12	U13	U23
C1	0.057 (3)	0.061 (3)	0.062 (3)	0.007 (3)	0.017 (2)	0.013 (2)
C2	0.055 (3)	0.051 (3)	0.066 (3)	0.006 (2)	0.012 (2)	0.010 (2)
C3	0.047 (2)	0.059 (3)	0.038 (2)	0.008 (2)	−0.0024 (18)	0.0035 (19)
C4	0.054 (3)	0.081 (4)	0.040 (2)	0.013 (3)	−0.001 (2)	0.002 (2)
C5	0.067 (4)	0.115 (6)	0.052 (3)	0.014 (4)	0.020 (3)	0.005 (3)
C6	0.071 (4)	0.103 (5)	0.059 (3)	−0.008 (3)	0.019 (3)	0.020 (3)
C7	0.069 (3)	0.062 (3)	0.056 (3)	−0.009 (3)	0.005 (3)	0.008 (2)
C8	0.040 (2)	0.063 (3)	0.037 (2)	−0.002 (2)	−0.0032 (17)	0.0036 (19)
C10	0.047 (2)	0.054 (3)	0.046 (2)	0.014 (2)	0.0038 (19)	−0.005 (2)
C11	0.063 (3)	0.065 (3)	0.071 (3)	0.008 (3)	0.009 (3)	0.008 (3)
C12	0.100 (5)	0.087 (4)	0.057 (3)	0.035 (4)	0.007 (3)	0.015 (3)
C13	0.072 (4)	0.093 (5)	0.061 (3)	0.030 (4)	−0.017 (3)	−0.022 (3)
C14	0.052 (3)	0.088 (4)	0.079 (4)	−0.002 (3)	−0.006 (3)	−0.019 (3)
C15	0.054 (3)	0.064 (3)	0.065 (3)	0.000 (3)	0.007 (2)	−0.002 (2)
N1	0.049 (2)	0.057 (2)	0.049 (2)	0.0085 (18)	0.0068 (17)	0.0049 (17)
O1	0.090 (3)	0.096 (3)	0.0455 (19)	0.027 (2)	0.0168 (18)	−0.0023 (19)
O2	0.068 (2)	0.062 (2)	0.090 (3)	0.001 (2)	−0.005 (2)	−0.014 (2)
S1	0.0549 (7)	0.0595 (8)	0.0494 (7)	0.0101 (6)	−0.0010 (5)	−0.0080 (5)
C9	0.074 (4)	0.090 (4)	0.050 (3)	0.030 (3)	0.006 (3)	0.002 (3)
Br1	0.0703 (18)	0.118 (3)	0.0437 (13)	0.035 (2)	0.0030 (8)	−0.0089 (11)
Br1A	0.120 (4)	0.059 (2)	0.068 (2)	−0.016 (3)	0.0095 (16)	0.0012 (13)

C1—C2	1.332 (7)	C11—C12	1.381 (4)
C1—N1	1.398 (7)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.386 (5)
C2—C3	1.448 (7)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.379 (4)
C3—C4	1.392 (7)	C13—H13	0.9300
C3—C8	1.398 (7)	C14—C15	1.382 (4)
C4—C5	1.380 (4)	C14—H14	0.9300
C4—C9	1.505 (8)	C15—H15	0.9300
C5—C6	1.381 (9)	N1—S1	1.661 (4)
C5—H5	0.9300	O1—S1	1.421 (4)
C6—C7	1.387 (9)	O2—S1	1.403 (4)
C6—H6	0.9300	C9—Br1	1.903 (6)
C7—C8	1.379 (7)	C9—Br1A	1.9115 (10)
C7—H7	0.9300	C9—H9A	0.9700
C8—N1	1.402 (6)	C9—H9B	0.9700
C10—C15	1.381 (4)	C9—H9C	0.9700
C10—C11	1.386 (4)	C9—H9D	0.9700
C10—S1	1.749 (4)
C2—C1—N1	110.6 (4)	C12—C13—H13	119.4
C2—C1—H1	124.7	C13—C14—C15	119.4 (5)
N1—C1—H1	124.7	C13—C14—H14	120.3
C1—C2—C3	107.3 (5)	C15—C14—H14	120.3
C1—C2—H2	126.4	C10—C15—C14	118.9 (5)
C3—C2—H2	126.4	C10—C15—H15	120.5
C4—C3—C8	120.7 (5)	C14—C15—H15	120.5
C4—C3—C2	132.0 (5)	C1—N1—C8	107.5 (4)
C8—C3—C2	107.2 (4)	C1—N1—S1	122.8 (4)
C5—C4—C3	117.0 (5)	C8—N1—S1	125.8 (3)
C5—C4—C9	121.2 (5)	O2—S1—O1	120.3 (3)
C3—C4—C9	121.7 (5)	O2—S1—N1	107.0 (2)
C4—C5—C6	121.4 (6)	O1—S1—N1	104.9 (2)
C4—C5—H5	119.3	O2—S1—C10	109.2 (2)
C6—C5—H5	119.3	O1—S1—C10	109.7 (2)
C5—C6—C7	122.6 (6)	N1—S1—C10	104.7 (2)
C5—C6—H6	118.7	C4—C9—Br1	111.1 (4)
C7—C6—H6	118.7	C4—C9—Br1A	111.9 (3)
C8—C7—C6	115.8 (6)	C4—C9—H9A	109.4
C8—C7—H7	122.1	Br1—C9—H9A	109.4
C6—C7—H7	122.1	Br1A—C9—H9A	114.5
C7—C8—C3	122.4 (5)	C4—C9—H9B	109.4
C7—C8—N1	130.3 (5)	Br1—C9—H9B	109.4
C3—C8—N1	107.3 (4)	Br1A—C9—H9B	103.3
C15—C10—C11	122.4 (4)	H9A—C9—H9B	108.0
C15—C10—S1	117.5 (3)	C4—C9—H9C	108.8
C11—C10—S1	120.1 (3)	Br1—C9—H9C	103.5
C12—C11—C10	118.1 (5)	Br1A—C9—H9C	108.9
C12—C11—H11	121.0	H9B—C9—H9C	114.5
C10—C11—H11	121.0	C4—C9—H9D	108.7
C11—C12—C13	120.0 (5)	Br1—C9—H9D	116.2
C11—C12—H12	120.0	Br1A—C9—H9D	110.3
C13—C12—H12	120.0	H9A—C9—H9D	101.4
C14—C13—C12	121.2 (5)	H9C—C9—H9D	108.2
C14—C13—H13	119.4
N1—C1—C2—C3	1.5 (6)	C13—C14—C15—C10	0.2 (9)
C1—C2—C3—C4	−178.7 (5)	C2—C1—N1—C8	−2.3 (6)
C1—C2—C3—C8	−0.2 (5)	C2—C1—N1—S1	−161.2 (4)
C8—C3—C4—C5	−0.4 (7)	C7—C8—N1—C1	−179.0 (5)
C2—C3—C4—C5	178.0 (5)	C3—C8—N1—C1	2.1 (5)
C8—C3—C4—C9	176.4 (4)	C7—C8—N1—S1	−20.9 (7)
C2—C3—C4—C9	−5.2 (7)	C3—C8—N1—S1	160.2 (3)
C3—C4—C5—C6	1.3 (8)	C1—N1—S1—O2	−159.9 (4)
C9—C4—C5—C6	−175.5 (5)	C8—N1—S1—O2	45.2 (4)
C4—C5—C6—C7	−0.2 (10)	C1—N1—S1—O1	−31.1 (5)
C5—C6—C7—C8	−1.6 (9)	C8—N1—S1—O1	174.0 (4)
C6—C7—C8—C3	2.5 (7)	C1—N1—S1—C10	84.4 (4)
C6—C7—C8—N1	−176.3 (5)	C8—N1—S1—C10	−70.6 (4)
C4—C3—C8—C7	−1.5 (7)	C15—C10—S1—O2	173.1 (4)
C2—C3—C8—C7	179.7 (4)	C11—C10—S1—O2	−6.3 (5)
C4—C3—C8—N1	177.5 (4)	C15—C10—S1—O1	39.4 (5)
C2—C3—C8—N1	−1.2 (5)	C11—C10—S1—O1	−140.0 (4)
C15—C10—C11—C12	−0.3 (8)	C15—C10—S1—N1	−72.7 (4)
S1—C10—C11—C12	179.0 (4)	C11—C10—S1—N1	108.0 (4)
C10—C11—C12—C13	−0.1 (9)	C5—C4—C9—Br1	84.3 (6)
C11—C12—C13—C14	0.6 (9)	C3—C4—C9—Br1	−92.4 (6)
C12—C13—C14—C15	−0.6 (9)	C5—C4—C9—Br1A	91.4 (7)
C11—C10—C15—C14	0.3 (8)	C3—C4—C9—Br1A	−85.3 (6)
S1—C10—C15—C14	−179.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cg1i	0.93	2.83	3.716 (6)	160
C9—H9D···Cg1ii	0.97	2.92	3.673 (5)	135
C1—H1···Cg2iii	0.93	2.69	3.584 (6)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯Cg1i	0.93	2.83	3.716 (6)	160
C9—H9D⋯Cg1ii	0.97	2.92	3.673 (5)	135
C1—H1⋯Cg2iii	0.93	2.69	3.584 (6)	162

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of atoms C3–C8 and C10–C15, respectively.