4-Bromo­meth­yl-1-phenyl­sulfon­yl-1H-indole

Chakkaravarthi, G.; Sureshbabu, R.; Mohanakrishnan, A.K.; Manivannan, V.

doi:10.1107/S1600536808007794

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o751

doi:10.1107/S1600536808007794

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4-Bromomethyl-1-phenylsulfonyl-1H-indole

G. Chakkaravarthi,^a ^* Radhakrishnan Sureshbabu,^b A. K. Mohanakrishnan ^b and V. Manivannan ^c

^aDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 12 March 2008; accepted 21 March 2008; online 29 March 2008)

In the title molecule, C₁₅H₁₂BrNO₂S, 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 intermolecular C—H⋯π interactions.

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_r = 350.23
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.199
S = 1.06
3606 reflections
191 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 1.25 e Å⁻³
Δρ_min = −0.54 e Å⁻³

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) -x+2, -y+1, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of atoms C3–C8 and C10–C15, respectively.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007794/cv2392sup1.cif

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

checkCIF report

Comment top

The indole derivatives are found to possess antibacterial (Okabe and Adachi, 1998) and antitumour (Schollmeyer et al., 1995) activities. In continuation of our studies in indole derivatives, we present the crystal structure of the title compound (I).

The geometric parameters of (I) (Fig. 1) agree with those in the reported structures (Chakkaravarthi et al., 2007; 2008) The indole mean plane and phenyl ring are nearly orthogonal to each other forming a dihedral angle of 88.19 (13)°. The plane of N1/S1/C1 makes the dihedral angles of 84.30 (14)°) and 72.38 (16)°, respectively, with the indole mean plane and phenyl ring. The sum of bond angles around N1 (356.9°) indicates that N1 is sp²-hybridized. The torsion angles C11-C10-S1-O2 [-6.3 (5)°] and C15-C10-S1-O1 [39.4 (5)°] indicate the syn conformation of the sulfonyl moiety.

The crystal packing exhibits weak intermolecular C—H···π interactions, involving the rings C3-C8 (centroid Cg1) and C10-C15 (centroid Cg2) (Table 1).

Related literature top

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 top

4-(Methyl)-1-(phenylsulfonyl)-1H-indole (1 g, 2.8 m.mol), N-bromo succinimide (0.5 g, 3 m.mol), azobis isobutyro nitrile (50 mg) were dissolved in 50 ml of carbon tetra chloride and refluxed on a waterbath for 2 h, then cooled to the room temperature. Succinimide was filtered off over sodium sulfate. Filtrate was evaporated under reduced pressure. Product was recrystallized from methanol. Yield: 80 %.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic labels and 50% probability displacement ellipsoids for non-H atoms. Only major parts of the disordered atoms are drawn.

4-Bromomethyl-1-phenylsulfonyl-1H-indole top

Crystal data top

C₁₅H₁₂BrNO₂S	F(000) = 704
M_r = 350.23	D_x = 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 = 2.5–25.8°
b = 8.2399 (7) Å	µ = 2.99 mm⁻¹
c = 15.4495 (11) Å	T = 295 K
β = 103.858 (3)°	Block, colourless
V = 1446.8 (2) Å³	0.18 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker Kappa APEX2 diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2160 reflections with I > 2s(I)
Graphite monochromator	R_int = 0.041
ω and ϕ scan	θ_max = 28.6°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.566, T_max = 0.620	k = −10→11
16472 measured reflections	l = −12→20

Refinement top

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.199	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.089P)² + 1.9138P] where P = (F_o² + 2F_c²)/3
3606 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 1.25 e Å⁻³
8 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₁₅H₁₂BrNO₂S	V = 1446.8 (2) Å³
M_r = 350.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7060 (9) Å	µ = 2.99 mm⁻¹
b = 8.2399 (7) Å	T = 295 K
c = 15.4495 (11) Å	0.18 × 0.18 × 0.16 mm
β = 103.858 (3)°

Data collection top

Bruker Kappa APEX2 diffractometer	3606 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2160 reflections with I > 2s(I)
T_min = 0.566, T_max = 0.620	R_int = 0.041
16472 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	8 restraints
wR(F²) = 0.199	H-atom parameters constrained
S = 1.06	Δρ_max = 1.25 e Å⁻³
3606 reflections	Δρ_min = −0.54 e Å⁻³
191 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂BrNO₂S
M_r	350.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.7060 (9), 8.2399 (7), 15.4495 (11)
β (°)	103.858 (3)
V (Å³)	1446.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.99
Crystal size (mm)	0.18 × 0.18 × 0.16

Data collection
Diffractometer	Bruker Kappa APEX2 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.566, 0.620
No. of measured, independent and observed [I > 2s(I)] reflections	16472, 3606, 2160
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.673

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.199, 1.06
No. of reflections	3606
No. of parameters	191
No. of restraints	8
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.25, −0.54

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2.

Acknowledgements

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

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