organic compounds
2-Bromo-1-(1-phenylsulfonyl-1H-indol-3-yl)propan-1-one
aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, bDepartment of Physics, Kundavai Nachiyar Govt College for Women, Thanjavur 613 007, India, cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India, and eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com
In the title compound, C17H14BrNO3S, the phenyl ring makes a dihedral angle of 89.78 (16)° with the plane of the indole ring system. The terminal Br atom and the methyl group are disordered over two sets of sites, with site occupancies of 0.860 (2) and 0.140 (2). In the crystal, molecules are linked into a chain along the b-axis direction by weak C—H⋯O hydrogen bonds. The chains are further linked by C—H⋯π interactions, forming layers parallel to the bc plane.
CCDC reference: 985849
Related literature
For the biological activity of indole derivatives, see: Andreani et al. (2001); Singh et al. (2000); Pomarnacka & Kozlarska-Kedra (2003); Srivastava & Pandeya (2011). For related structures, see: Umadevi et al. (2013); Kanchanadevi et al. (2014).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008).
Supporting information
CCDC reference: 985849
10.1107/S1600536814002864/is5339sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814002864/is5339Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814002864/is5339Isup3.cml
A solution of 1-[1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one (1 g, 3.194 mmol) and PTT (phenyltrimethylammonium tribromide) (1.32 g, 3.514 mmol) in dry THF (20 ml) was stirred at room temperature for 3 h. After completion of the reaction (monitored by TLC), it was poured into crushed ice (100 g). The solid obtained was filtered and washed with MeOH (5 ml) to afford 2-bromo-1-[1-(phenylsulfonyl)-1H-indol-3-yl]propan-1-one (1.14 g, yield 91%; melting point 130–132 °C).
The terminal bromine atom and the methyl group are disordered over two positions. The site occupancy factors of disordered atoms were refined to 0.860 (2) and 0.140 (2). In the
EADP was used for atoms C17 and C17A. The bond distances of C16—C17 and C16—C17A were restrained to be 1.5200 (1) and 1.5200 (5) Å, respectively, and the distances of C16—Br1 and C16—Br1A were restrained to be 1.9100 (1) and 1.9100 (5) Å, respectively. Also the distance of C17A···Br1A was restrained to be 2.85 (1) Å. H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for C—H, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3.Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008).C17H14BrNO3S | F(000) = 792 |
Mr = 392.26 | Dx = 1.560 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4350 reflections |
a = 8.7539 (3) Å | θ = 2.2–28.4° |
b = 10.9968 (4) Å | µ = 2.60 mm−1 |
c = 17.5801 (7) Å | T = 295 K |
β = 99.231 (2)° | Block, yellow |
V = 1670.43 (11) Å3 | 0.35 × 0.25 × 0.25 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 4141 independent reflections |
Radiation source: fine-focus sealed tube | 2334 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 0 pixels mm-1 | θmax = 28.5°, θmin = 2.2° |
ω and φ scans | h = −11→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→14 |
Tmin = 0.416, Tmax = 0.522 | l = −21→23 |
15009 measured reflections |
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)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.149 | w = 1/[σ2(Fo2) + (0.0673P)2 + 0.7073P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4141 reflections | Δρmax = 0.41 e Å−3 |
222 parameters | Δρmin = −0.51 e Å−3 |
5 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0037 (9) |
C17H14BrNO3S | V = 1670.43 (11) Å3 |
Mr = 392.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.7539 (3) Å | µ = 2.60 mm−1 |
b = 10.9968 (4) Å | T = 295 K |
c = 17.5801 (7) Å | 0.35 × 0.25 × 0.25 mm |
β = 99.231 (2)° |
Bruker APEXII CCD diffractometer | 4141 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2334 reflections with I > 2σ(I) |
Tmin = 0.416, Tmax = 0.522 | Rint = 0.034 |
15009 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 5 restraints |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.41 e Å−3 |
4141 reflections | Δρmin = −0.51 e Å−3 |
222 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.7170 (3) | 0.2542 (3) | 0.30787 (16) | 0.0382 (7) | |
C2 | 0.6804 (4) | 0.1348 (3) | 0.28691 (18) | 0.0480 (8) | |
H2 | 0.7480 | 0.0850 | 0.2655 | 0.058* | |
C3 | 0.5365 (4) | 0.0944 (3) | 0.2998 (2) | 0.0558 (9) | |
H3 | 0.5071 | 0.0148 | 0.2870 | 0.067* | |
C4 | 0.4359 (4) | 0.1688 (3) | 0.3310 (2) | 0.0627 (10) | |
H4 | 0.3398 | 0.1387 | 0.3380 | 0.075* | |
C5 | 0.4753 (4) | 0.2878 (3) | 0.3522 (2) | 0.0552 (9) | |
H5 | 0.4072 | 0.3373 | 0.3735 | 0.066* | |
C6 | 0.6184 (3) | 0.3308 (3) | 0.34090 (16) | 0.0392 (7) | |
C7 | 0.6963 (3) | 0.4468 (2) | 0.35599 (16) | 0.0391 (7) | |
C8 | 0.8349 (3) | 0.4370 (2) | 0.33195 (16) | 0.0375 (7) | |
H8 | 0.9074 | 0.4992 | 0.3341 | 0.045* | |
C9 | 0.8963 (3) | 0.3192 (3) | 0.15480 (17) | 0.0427 (7) | |
C10 | 0.9085 (4) | 0.4343 (3) | 0.12403 (19) | 0.0587 (9) | |
H10 | 0.9658 | 0.4947 | 0.1527 | 0.070* | |
C11 | 0.8349 (5) | 0.4573 (4) | 0.0508 (2) | 0.0803 (12) | |
H11 | 0.8417 | 0.5339 | 0.0292 | 0.096* | |
C12 | 0.7501 (5) | 0.3665 (4) | 0.0088 (2) | 0.0820 (13) | |
H12 | 0.6992 | 0.3830 | −0.0407 | 0.098* | |
C13 | 0.7405 (5) | 0.2530 (4) | 0.0393 (2) | 0.0804 (13) | |
H13 | 0.6845 | 0.1926 | 0.0101 | 0.096* | |
C14 | 0.8121 (4) | 0.2279 (3) | 0.1120 (2) | 0.0614 (9) | |
H14 | 0.8050 | 0.1508 | 0.1329 | 0.074* | |
C15 | 0.6362 (4) | 0.5538 (3) | 0.39046 (19) | 0.0511 (8) | |
C16 | 0.7409 (4) | 0.6635 (2) | 0.40341 (9) | 0.0651 (10) | |
H16A | 0.8186 | 0.6547 | 0.3694 | 0.078* | 0.860 (2) |
H16B | 0.7916 | 0.6656 | 0.3576 | 0.078* | 0.140 (2) |
Br1 | 0.84813 (7) | 0.65595 (6) | 0.50680 (4) | 0.0973 (3) | 0.860 (2) |
C17 | 0.6681 (10) | 0.7883 (4) | 0.3880 (5) | 0.0539 (15) | 0.860 (2) |
H17A | 0.7036 | 0.8411 | 0.4307 | 0.081* | 0.860 (2) |
H17B | 0.5575 | 0.7812 | 0.3817 | 0.081* | 0.860 (2) |
H17C | 0.6973 | 0.8215 | 0.3419 | 0.081* | 0.860 (2) |
Br1A | 0.6298 (11) | 0.8071 (6) | 0.3977 (7) | 0.132 (4) | 0.140 (2) |
C17A | 0.875 (2) | 0.6591 (18) | 0.4701 (12) | 0.0539 (15) | 0.140 (2) |
H17D | 0.9557 | 0.7124 | 0.4596 | 0.081* | 0.140 (2) |
H17E | 0.9138 | 0.5775 | 0.4763 | 0.081* | 0.140 (2) |
H17F | 0.8396 | 0.6846 | 0.5166 | 0.081* | 0.140 (2) |
N1 | 0.8539 (3) | 0.3213 (2) | 0.30363 (13) | 0.0384 (6) | |
O1 | 1.0168 (3) | 0.16368 (19) | 0.25653 (14) | 0.0591 (6) | |
O2 | 1.1079 (2) | 0.3760 (2) | 0.27067 (13) | 0.0526 (6) | |
O3 | 0.5058 (3) | 0.5548 (2) | 0.40600 (18) | 0.0778 (8) | |
S1 | 0.98775 (9) | 0.29060 (7) | 0.24862 (4) | 0.0422 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0438 (16) | 0.0389 (15) | 0.0298 (16) | 0.0014 (13) | −0.0003 (12) | 0.0057 (12) |
C2 | 0.059 (2) | 0.0392 (17) | 0.0421 (19) | −0.0028 (14) | −0.0019 (15) | 0.0011 (13) |
C3 | 0.060 (2) | 0.0464 (18) | 0.056 (2) | −0.0136 (17) | −0.0088 (16) | 0.0034 (16) |
C4 | 0.0454 (19) | 0.065 (2) | 0.074 (3) | −0.0139 (18) | −0.0001 (17) | 0.0101 (19) |
C5 | 0.0441 (18) | 0.058 (2) | 0.063 (2) | 0.0016 (16) | 0.0069 (15) | 0.0098 (17) |
C6 | 0.0413 (16) | 0.0405 (15) | 0.0340 (16) | 0.0009 (13) | 0.0004 (12) | 0.0080 (12) |
C7 | 0.0454 (16) | 0.0353 (15) | 0.0355 (16) | 0.0031 (13) | 0.0034 (12) | 0.0027 (12) |
C8 | 0.0464 (17) | 0.0298 (14) | 0.0357 (16) | −0.0021 (12) | 0.0047 (12) | −0.0002 (11) |
C9 | 0.0470 (17) | 0.0435 (17) | 0.0393 (17) | 0.0018 (13) | 0.0115 (13) | −0.0037 (13) |
C10 | 0.083 (2) | 0.0438 (19) | 0.047 (2) | −0.0007 (17) | 0.0053 (18) | −0.0021 (15) |
C11 | 0.118 (4) | 0.063 (2) | 0.056 (3) | 0.003 (2) | 0.004 (2) | 0.010 (2) |
C12 | 0.097 (3) | 0.107 (4) | 0.037 (2) | −0.008 (3) | −0.004 (2) | −0.001 (2) |
C13 | 0.099 (3) | 0.098 (3) | 0.042 (2) | −0.033 (3) | 0.008 (2) | −0.012 (2) |
C14 | 0.078 (2) | 0.061 (2) | 0.047 (2) | −0.0192 (19) | 0.0146 (18) | −0.0042 (17) |
C15 | 0.057 (2) | 0.051 (2) | 0.047 (2) | 0.0062 (16) | 0.0141 (16) | 0.0018 (14) |
C16 | 0.080 (3) | 0.051 (2) | 0.070 (3) | −0.0090 (18) | 0.029 (2) | −0.0180 (17) |
Br1 | 0.0956 (5) | 0.0997 (5) | 0.0870 (5) | −0.0029 (3) | −0.0142 (3) | −0.0100 (3) |
C17 | 0.067 (4) | 0.023 (2) | 0.071 (4) | 0.016 (2) | 0.008 (3) | 0.009 (2) |
Br1A | 0.118 (6) | 0.078 (3) | 0.192 (7) | 0.027 (3) | 0.004 (4) | −0.038 (4) |
C17A | 0.067 (4) | 0.023 (2) | 0.071 (4) | 0.016 (2) | 0.008 (3) | 0.009 (2) |
N1 | 0.0432 (14) | 0.0363 (13) | 0.0356 (14) | −0.0015 (10) | 0.0062 (10) | −0.0010 (10) |
O1 | 0.0659 (15) | 0.0400 (12) | 0.0727 (17) | 0.0185 (10) | 0.0151 (12) | 0.0072 (10) |
O2 | 0.0369 (11) | 0.0555 (13) | 0.0640 (15) | −0.0048 (10) | 0.0040 (10) | −0.0037 (11) |
O3 | 0.0651 (17) | 0.0646 (16) | 0.111 (2) | 0.0071 (13) | 0.0367 (16) | −0.0143 (15) |
S1 | 0.0431 (4) | 0.0378 (4) | 0.0458 (5) | 0.0067 (3) | 0.0078 (3) | 0.0012 (3) |
C1—C2 | 1.387 (4) | C12—C13 | 1.366 (6) |
C1—C6 | 1.398 (4) | C12—H12 | 0.9300 |
C1—N1 | 1.420 (4) | C13—C14 | 1.359 (5) |
C2—C3 | 1.388 (5) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C3—C4 | 1.379 (5) | C15—O3 | 1.216 (4) |
C3—H3 | 0.9300 | C15—C16 | 1.511 (4) |
C4—C5 | 1.389 (5) | C16—C17 | 1.5190 (10) |
C4—H4 | 0.9300 | C16—C17A | 1.520 (5) |
C5—C6 | 1.382 (4) | C16—Br1A | 1.849 (4) |
C5—H5 | 0.9300 | C16—Br1 | 1.9092 (10) |
C6—C7 | 1.450 (4) | C16—H16A | 0.9800 |
C7—C8 | 1.352 (4) | C16—H16B | 0.9800 |
C7—C15 | 1.460 (4) | C17—H17A | 0.9600 |
C8—N1 | 1.386 (3) | C17—H17B | 0.9600 |
C8—H8 | 0.9300 | C17—H17C | 0.9600 |
C9—C10 | 1.388 (4) | C17A—H17D | 0.9600 |
C9—C14 | 1.392 (5) | C17A—H17E | 0.9600 |
C9—S1 | 1.743 (3) | C17A—H17F | 0.9600 |
C10—C11 | 1.368 (5) | N1—S1 | 1.669 (2) |
C10—H10 | 0.9300 | O1—S1 | 1.422 (2) |
C11—C12 | 1.384 (6) | O2—S1 | 1.417 (2) |
C11—H11 | 0.9300 | ||
C2—C1—C6 | 123.3 (3) | C13—C14—C9 | 119.1 (3) |
C2—C1—N1 | 129.7 (3) | C13—C14—H14 | 120.5 |
C6—C1—N1 | 107.0 (2) | C9—C14—H14 | 120.5 |
C1—C2—C3 | 115.9 (3) | O3—C15—C7 | 121.0 (3) |
C1—C2—H2 | 122.0 | O3—C15—C16 | 121.8 (3) |
C3—C2—H2 | 122.0 | C7—C15—C16 | 117.1 (3) |
C4—C3—C2 | 121.9 (3) | C15—C16—C17 | 117.9 (4) |
C4—C3—H3 | 119.0 | C15—C16—C17A | 117.7 (10) |
C2—C3—H3 | 119.0 | C15—C16—Br1A | 111.9 (4) |
C3—C4—C5 | 121.3 (3) | C17A—C16—Br1A | 113.8 (6) |
C3—C4—H4 | 119.4 | C15—C16—Br1 | 107.61 (19) |
C5—C4—H4 | 119.4 | C17—C16—Br1 | 109.7 (4) |
C6—C5—C4 | 118.4 (3) | C15—C16—H16A | 107.0 |
C6—C5—H5 | 120.8 | C17—C16—H16A | 107.0 |
C4—C5—H5 | 120.8 | Br1—C16—H16A | 107.0 |
C5—C6—C1 | 119.2 (3) | C15—C16—H16B | 103.8 |
C5—C6—C7 | 133.2 (3) | C17A—C16—H16B | 103.8 |
C1—C6—C7 | 107.6 (2) | Br1A—C16—H16B | 103.8 |
C8—C7—C6 | 107.0 (2) | C16—C17—H17A | 109.5 |
C8—C7—C15 | 126.5 (3) | C16—C17—H17B | 109.5 |
C6—C7—C15 | 126.5 (3) | H17A—C17—H17B | 109.5 |
C7—C8—N1 | 110.6 (2) | C16—C17—H17C | 109.5 |
C7—C8—H8 | 124.7 | H17A—C17—H17C | 109.5 |
N1—C8—H8 | 124.7 | H17B—C17—H17C | 109.5 |
C10—C9—C14 | 121.0 (3) | C16—C17A—H17D | 109.5 |
C10—C9—S1 | 118.7 (2) | C16—C17A—H17E | 109.5 |
C14—C9—S1 | 120.3 (2) | H17D—C17A—H17E | 109.5 |
C11—C10—C9 | 118.8 (3) | C16—C17A—H17F | 109.5 |
C11—C10—H10 | 120.6 | H17D—C17A—H17F | 109.5 |
C9—C10—H10 | 120.6 | H17E—C17A—H17F | 109.5 |
C10—C11—C12 | 120.0 (4) | C8—N1—C1 | 107.9 (2) |
C10—C11—H11 | 120.0 | C8—N1—S1 | 122.02 (19) |
C12—C11—H11 | 120.0 | C1—N1—S1 | 127.03 (19) |
C13—C12—C11 | 120.7 (4) | O2—S1—O1 | 120.71 (14) |
C13—C12—H12 | 119.6 | O2—S1—N1 | 105.46 (12) |
C11—C12—H12 | 119.6 | O1—S1—N1 | 105.86 (13) |
C14—C13—C12 | 120.4 (4) | O2—S1—C9 | 110.36 (14) |
C14—C13—H13 | 119.8 | O1—S1—C9 | 108.50 (14) |
C12—C13—H13 | 119.8 | N1—S1—C9 | 104.67 (13) |
C6—C1—C2—C3 | 0.7 (4) | C6—C7—C15—C16 | 177.8 (2) |
N1—C1—C2—C3 | 178.7 (3) | O3—C15—C16—C17 | −37.3 (5) |
C1—C2—C3—C4 | 0.5 (5) | C7—C15—C16—C17 | 140.8 (4) |
C2—C3—C4—C5 | −1.1 (5) | O3—C15—C16—C17A | 106.8 (12) |
C3—C4—C5—C6 | 0.4 (5) | C7—C15—C16—C17A | −75.1 (12) |
C4—C5—C6—C1 | 0.8 (4) | O3—C15—C16—Br1A | −27.8 (5) |
C4—C5—C6—C7 | −179.8 (3) | C7—C15—C16—Br1A | 150.3 (4) |
C2—C1—C6—C5 | −1.4 (4) | O3—C15—C16—Br1 | 87.4 (3) |
N1—C1—C6—C5 | −179.7 (2) | C7—C15—C16—Br1 | −94.5 (3) |
C2—C1—C6—C7 | 179.1 (3) | C7—C8—N1—C1 | 1.7 (3) |
N1—C1—C6—C7 | 0.7 (3) | C7—C8—N1—S1 | 163.2 (2) |
C5—C6—C7—C8 | −179.2 (3) | C2—C1—N1—C8 | −179.7 (3) |
C1—C6—C7—C8 | 0.3 (3) | C6—C1—N1—C8 | −1.5 (3) |
C5—C6—C7—C15 | 0.7 (5) | C2—C1—N1—S1 | 20.1 (4) |
C1—C6—C7—C15 | −179.8 (3) | C6—C1—N1—S1 | −161.7 (2) |
C6—C7—C8—N1 | −1.3 (3) | C8—N1—S1—O2 | 28.1 (2) |
C15—C7—C8—N1 | 178.9 (3) | C1—N1—S1—O2 | −174.2 (2) |
C14—C9—C10—C11 | 0.7 (5) | C8—N1—S1—O1 | 157.1 (2) |
S1—C9—C10—C11 | −179.1 (3) | C1—N1—S1—O1 | −45.2 (3) |
C9—C10—C11—C12 | 0.0 (6) | C8—N1—S1—C9 | −88.4 (2) |
C10—C11—C12—C13 | −0.8 (7) | C1—N1—S1—C9 | 69.3 (2) |
C11—C12—C13—C14 | 1.1 (7) | C10—C9—S1—O2 | −21.3 (3) |
C12—C13—C14—C9 | −0.4 (6) | C14—C9—S1—O2 | 158.9 (3) |
C10—C9—C14—C13 | −0.4 (5) | C10—C9—S1—O1 | −155.7 (3) |
S1—C9—C14—C13 | 179.3 (3) | C14—C9—S1—O1 | 24.6 (3) |
C8—C7—C15—O3 | 175.7 (3) | C10—C9—S1—N1 | 91.7 (3) |
C6—C7—C15—O3 | −4.1 (5) | C14—C9—S1—N1 | −88.0 (3) |
C8—C7—C15—C16 | −2.4 (4) |
Cg2 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.93 | 2.57 | 3.312 (4) | 137 |
C10—H10···O1i | 0.93 | 2.44 | 3.280 (4) | 150 |
C12—H12···Cg2ii | 0.93 | 2.72 | 3.528 (2) | 146 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2. |
Cg2 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.93 | 2.57 | 3.312 (4) | 137 |
C10—H10···O1i | 0.93 | 2.44 | 3.280 (4) | 150 |
C12—H12···Cg2ii | 0.93 | 2.72 | 3.528 (2) | 146 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2. |
Acknowledgements
CR acknowledges AMET University management, India, for their kind support.
References
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Indole derivatives exhibit antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). These derivatives also exhibit antimicrobial, antibiotic, analgesic, anticancer and anti-HIV (Pomarnacka & Kozlarska-Kedra, 2003; Srivastava & Pandeya, 2011) activities.
The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structures (Umadevi et al., 2013; Kanchanadevi et al., 2014). The phenyl ring makes a dihedral angle of 89.78 (16)° with the indole ring system. The terminal bromine atom and the methyl group are disordered over two positions with site occupancies of 0.860 (2) and 0.140 (2). The sum of bond angles around the atom N1 [356.7 (3) °] indicates sp2 hybridized state of atom N1 in the molecule. The crystal packing is controlled by weak C—H···O and C—H···π interactions (Table 1).