organic compounds
(E)-1-[2-(2-Nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl]propan-1-one
aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India, bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, 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, C25H20N2O5S, the phenyl ring makes dihedral angles of 89.88 (8) and 13.98 (8)°, respectively, with the indole ring system and the nitrobenzene ring. The dihedral angle between the indole ring system and the nitrobenzene ring is 88.48 (11)°. The molecular structure is stabilized by a weak intramolecular C—H⋯O interaction. In the crystal, π–π interactions, with centroid–centroid distances of 3.6741 (18) and 3.8873 (17) Å, link the molecules into layers parallel to the ab plane.
CCDC reference: 980674
Related literature
For biological activity of indole derivatives, see: Andreani et al. (2001); Quetin-Leclercq (1994); Mukhopadhyay et al. (1981); Singh et al. (2000). 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; 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.
Supporting information
CCDC reference: 980674
10.1107/S1600536814000506/is5331sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000506/is5331Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000506/is5331Isup3.cml
A solution of 1-[2-(bromomethyl)-1-(phenylsulfonyl)-1H-indol-3-yl] propan-1-one (5 g, 12.31 mmol) and triphenylphosphine (3.5 g, 13.54 mmol) in dry THF (100 ml) was refluxed for 6 h. After consumption of the starting material, the solvent was removed under vaccum and the solid was washed with diethyl ether to give the phosphonium salt. Then, the mixture of phosphonium salt (8 g, 11.97 mmol), 2-nitrobenzaldehydes (1.99 g, 13.17 mmol) and K2CO3 (3.30 g, 23.95 mmol) in DCM (70 ml) was stirred at room temperature for 24 h. After completion of the reaction (monitored by TLC), it was diluted using DCM (30 ml), washed with water (2 × 100 ml) and dried (Na2SO4). Removal of solvent followed by trituration of the crude product with MeOH (20 ml) afforded (E)-1-[2-(2-nitrostyryl)-1-(phenylsulfonyl)-1H- indol-3-yl]propan-1-one as yellow solid (4.30 g, 76%) with melting point 168–170 °C.
H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic CH, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3.
Indole derivatives exhibits antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). Some of the indole
extracted from plants possess interesting cytotoxic and antiparasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981).The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Umadevi et al., 2013). The phenyl ring makes a dihedral angles of 89.88 (8) and 13.98 (8)° with the indole ring system and the nitro benzene ring, respectively. The sum of bond angles around the atom N1 [356.03°] indicates sp2 hybridized. The molecular structure is stabilized by a weak intramolecular C—H···O interaction.
For biological activity of indole derivatives, see: Andreani et al. (2001); Quetin-Leclercq (1994); Mukhopadhyay et al. (1981); Singh et al. (2000). For related structures, see: Umadevi et al. (2013); Kanchanadevi et al. (2014).
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).Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms. |
C25H20N2O5S | F(000) = 1920 |
Mr = 460.49 | Dx = 1.423 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5350 reflections |
a = 21.6100 (18) Å | θ = 2.0–28.3° |
b = 8.3072 (7) Å | µ = 0.19 mm−1 |
c = 25.898 (3) Å | T = 295 K |
β = 112.379 (2)° | Block, yellow |
V = 4299.1 (7) Å3 | 0.30 × 0.25 × 0.25 mm |
Z = 8 |
Bruker APEXII CCD diffractometer | 5343 independent reflections |
Radiation source: fine-focus sealed tube | 3700 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 0 pixels mm-1 | θmax = 28.3°, θmin = 2.0° |
ω and φ scans | h = −28→28 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −11→11 |
Tmin = 0.945, Tmax = 0.955 | l = −32→34 |
40633 measured reflections |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0587P)2 + 6.0066P] where P = (Fo2 + 2Fc2)/3 |
5343 reflections | (Δ/σ)max = 0.001 |
299 parameters | Δρmax = 0.66 e Å−3 |
0 restraints | Δρmin = −0.67 e Å−3 |
C25H20N2O5S | V = 4299.1 (7) Å3 |
Mr = 460.49 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.6100 (18) Å | µ = 0.19 mm−1 |
b = 8.3072 (7) Å | T = 295 K |
c = 25.898 (3) Å | 0.30 × 0.25 × 0.25 mm |
β = 112.379 (2)° |
Bruker APEXII CCD diffractometer | 5343 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3700 reflections with I > 2σ(I) |
Tmin = 0.945, Tmax = 0.955 | Rint = 0.044 |
40633 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.66 e Å−3 |
5343 reflections | Δρmin = −0.67 e Å−3 |
299 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.15190 (11) | −0.0496 (3) | 0.50378 (9) | 0.0411 (5) | |
C2 | 0.08840 (13) | −0.1098 (3) | 0.47316 (10) | 0.0544 (7) | |
H2 | 0.0544 | −0.1071 | 0.4869 | 0.065* | |
C3 | 0.07820 (16) | −0.1738 (3) | 0.42139 (11) | 0.0649 (8) | |
H3 | 0.0364 | −0.2157 | 0.3997 | 0.078* | |
C4 | 0.12856 (17) | −0.1769 (3) | 0.40107 (11) | 0.0647 (8) | |
H4 | 0.1199 | −0.2207 | 0.3659 | 0.078* | |
C5 | 0.19136 (15) | −0.1172 (3) | 0.43131 (10) | 0.0561 (7) | |
H5 | 0.2249 | −0.1208 | 0.4171 | 0.067* | |
C6 | 0.20352 (12) | −0.0506 (3) | 0.48417 (9) | 0.0433 (5) | |
C7 | 0.26149 (11) | 0.0260 (3) | 0.52583 (9) | 0.0400 (5) | |
C8 | 0.24458 (10) | 0.0690 (3) | 0.56984 (8) | 0.0356 (5) | |
C9 | 0.28201 (11) | 0.1582 (3) | 0.62103 (9) | 0.0384 (5) | |
H9 | 0.2654 | 0.2575 | 0.6262 | 0.046* | |
C10 | 0.33832 (11) | 0.1058 (3) | 0.66058 (8) | 0.0384 (5) | |
H10 | 0.3533 | 0.0032 | 0.6568 | 0.046* | |
C11 | 0.37820 (10) | 0.2010 (3) | 0.71009 (9) | 0.0374 (5) | |
C12 | 0.37603 (13) | 0.3685 (3) | 0.70753 (11) | 0.0503 (6) | |
H12 | 0.3482 | 0.4178 | 0.6746 | 0.060* | |
C13 | 0.41344 (15) | 0.4635 (4) | 0.75177 (14) | 0.0651 (8) | |
H13 | 0.4098 | 0.5749 | 0.7487 | 0.078* | |
C14 | 0.45614 (14) | 0.3952 (4) | 0.80052 (12) | 0.0661 (8) | |
H14 | 0.4814 | 0.4598 | 0.8304 | 0.079* | |
C15 | 0.46118 (13) | 0.2320 (4) | 0.80475 (10) | 0.0566 (7) | |
H15 | 0.4906 | 0.1847 | 0.8374 | 0.068* | |
C16 | 0.42243 (11) | 0.1363 (3) | 0.76039 (9) | 0.0415 (5) | |
C17 | 0.16595 (11) | −0.1823 (3) | 0.63322 (9) | 0.0372 (5) | |
C18 | 0.22218 (12) | −0.1958 (3) | 0.68196 (10) | 0.0479 (6) | |
H18 | 0.2470 | −0.1051 | 0.6987 | 0.057* | |
C19 | 0.24071 (14) | −0.3460 (3) | 0.70527 (11) | 0.0578 (7) | |
H19 | 0.2782 | −0.3571 | 0.7381 | 0.069* | |
C20 | 0.20406 (15) | −0.4794 (3) | 0.68021 (11) | 0.0549 (7) | |
H20 | 0.2169 | −0.5802 | 0.6964 | 0.066* | |
C21 | 0.14871 (15) | −0.4656 (3) | 0.63161 (11) | 0.0548 (7) | |
H21 | 0.1243 | −0.5567 | 0.6149 | 0.066* | |
C22 | 0.12933 (12) | −0.3159 (3) | 0.60758 (10) | 0.0473 (6) | |
H22 | 0.0920 | −0.3055 | 0.5745 | 0.057* | |
C23 | 0.32263 (14) | 0.0616 (4) | 0.51526 (11) | 0.0565 (7) | |
C25 | 0.43883 (15) | 0.1576 (5) | 0.53443 (13) | 0.0788 (10) | |
H25A | 0.4556 | 0.0538 | 0.5299 | 0.118* | |
H25B | 0.4744 | 0.2201 | 0.5605 | 0.118* | |
H25C | 0.4216 | 0.2120 | 0.4991 | 0.118* | |
N1 | 0.17663 (9) | 0.0287 (2) | 0.55666 (7) | 0.0387 (4) | |
N2 | 0.42953 (12) | −0.0372 (3) | 0.76957 (9) | 0.0551 (6) | |
O1 | 0.07086 (8) | 0.0081 (2) | 0.57260 (8) | 0.0582 (5) | |
O2 | 0.16992 (9) | 0.1277 (2) | 0.64547 (7) | 0.0495 (4) | |
O3 | 0.38239 (11) | −0.1241 (2) | 0.74363 (8) | 0.0685 (6) | |
O4 | 0.48249 (12) | −0.0875 (3) | 0.80380 (10) | 0.0950 (8) | |
O5 | 0.32135 (15) | 0.0336 (6) | 0.46959 (12) | 0.1606 (19) | |
C24 | 0.38311 (13) | 0.1372 (4) | 0.55629 (11) | 0.0596 (7) | |
H24A | 0.3994 | 0.0716 | 0.5898 | 0.072* | |
H24B | 0.3714 | 0.2420 | 0.5664 | 0.072* | |
S1 | 0.14097 (3) | 0.00862 (7) | 0.60389 (2) | 0.04073 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0433 (12) | 0.0396 (12) | 0.0310 (10) | 0.0040 (9) | 0.0034 (9) | 0.0030 (9) |
C2 | 0.0478 (14) | 0.0557 (15) | 0.0461 (13) | −0.0036 (12) | 0.0025 (11) | 0.0019 (12) |
C3 | 0.0667 (18) | 0.0546 (16) | 0.0486 (15) | −0.0027 (14) | −0.0058 (14) | −0.0016 (13) |
C4 | 0.089 (2) | 0.0498 (15) | 0.0366 (13) | 0.0053 (15) | 0.0028 (14) | −0.0063 (11) |
C5 | 0.0748 (18) | 0.0494 (14) | 0.0405 (13) | 0.0120 (13) | 0.0180 (13) | −0.0017 (11) |
C6 | 0.0512 (13) | 0.0389 (12) | 0.0339 (11) | 0.0084 (10) | 0.0095 (10) | 0.0037 (9) |
C7 | 0.0407 (12) | 0.0423 (12) | 0.0352 (11) | 0.0064 (9) | 0.0123 (9) | 0.0031 (9) |
C8 | 0.0356 (11) | 0.0343 (10) | 0.0332 (10) | 0.0040 (8) | 0.0090 (8) | 0.0050 (8) |
C9 | 0.0389 (11) | 0.0376 (11) | 0.0385 (11) | 0.0001 (9) | 0.0145 (9) | −0.0019 (9) |
C10 | 0.0428 (12) | 0.0363 (11) | 0.0347 (10) | 0.0010 (9) | 0.0131 (9) | 0.0001 (9) |
C11 | 0.0344 (10) | 0.0423 (12) | 0.0367 (11) | −0.0020 (9) | 0.0147 (9) | −0.0035 (9) |
C12 | 0.0466 (13) | 0.0431 (13) | 0.0569 (15) | −0.0023 (11) | 0.0149 (11) | −0.0004 (11) |
C13 | 0.0616 (18) | 0.0473 (15) | 0.086 (2) | −0.0141 (13) | 0.0275 (16) | −0.0191 (14) |
C14 | 0.0574 (17) | 0.078 (2) | 0.0618 (17) | −0.0217 (15) | 0.0214 (14) | −0.0309 (16) |
C15 | 0.0452 (14) | 0.085 (2) | 0.0363 (12) | −0.0074 (13) | 0.0113 (11) | −0.0076 (13) |
C16 | 0.0363 (11) | 0.0537 (14) | 0.0349 (11) | −0.0011 (10) | 0.0141 (9) | −0.0005 (10) |
C17 | 0.0365 (11) | 0.0407 (11) | 0.0379 (11) | −0.0014 (9) | 0.0182 (9) | −0.0015 (9) |
C18 | 0.0489 (13) | 0.0472 (13) | 0.0415 (12) | −0.0043 (11) | 0.0105 (11) | 0.0003 (10) |
C19 | 0.0615 (16) | 0.0576 (16) | 0.0476 (14) | 0.0064 (13) | 0.0131 (12) | 0.0084 (12) |
C20 | 0.0778 (19) | 0.0422 (13) | 0.0542 (15) | 0.0059 (13) | 0.0358 (14) | 0.0061 (11) |
C21 | 0.0716 (18) | 0.0438 (14) | 0.0562 (15) | −0.0095 (12) | 0.0324 (14) | −0.0099 (11) |
C22 | 0.0475 (13) | 0.0507 (14) | 0.0432 (13) | −0.0071 (11) | 0.0168 (11) | −0.0063 (11) |
C23 | 0.0539 (15) | 0.0727 (18) | 0.0490 (14) | 0.0045 (13) | 0.0263 (12) | −0.0045 (13) |
C25 | 0.0535 (17) | 0.117 (3) | 0.071 (2) | −0.0062 (18) | 0.0306 (15) | 0.0107 (19) |
N1 | 0.0353 (9) | 0.0444 (10) | 0.0335 (9) | −0.0002 (8) | 0.0096 (7) | 0.0003 (8) |
N2 | 0.0550 (13) | 0.0605 (14) | 0.0427 (11) | 0.0093 (11) | 0.0106 (10) | 0.0101 (10) |
O1 | 0.0334 (9) | 0.0724 (12) | 0.0652 (11) | 0.0094 (8) | 0.0146 (8) | 0.0086 (10) |
O2 | 0.0594 (10) | 0.0413 (9) | 0.0533 (10) | 0.0017 (8) | 0.0276 (8) | −0.0066 (7) |
O3 | 0.0716 (13) | 0.0500 (11) | 0.0676 (12) | −0.0019 (10) | 0.0083 (10) | 0.0098 (10) |
O4 | 0.0792 (15) | 0.0911 (17) | 0.0785 (15) | 0.0235 (13) | −0.0106 (12) | 0.0267 (13) |
O5 | 0.099 (2) | 0.318 (5) | 0.0942 (19) | −0.081 (3) | 0.0701 (17) | −0.103 (3) |
C24 | 0.0500 (15) | 0.0769 (19) | 0.0548 (15) | −0.0035 (13) | 0.0232 (12) | 0.0066 (14) |
S1 | 0.0360 (3) | 0.0430 (3) | 0.0434 (3) | 0.0043 (2) | 0.0154 (2) | 0.0012 (2) |
C1—C6 | 1.390 (3) | C15—C16 | 1.386 (3) |
C1—C2 | 1.390 (3) | C15—H15 | 0.9300 |
C1—N1 | 1.424 (3) | C16—N2 | 1.460 (3) |
C2—C3 | 1.380 (4) | C17—C22 | 1.378 (3) |
C2—H2 | 0.9300 | C17—C18 | 1.384 (3) |
C3—C4 | 1.378 (5) | C17—S1 | 1.753 (2) |
C3—H3 | 0.9300 | C18—C19 | 1.378 (4) |
C4—C5 | 1.376 (4) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—C20 | 1.373 (4) |
C5—C6 | 1.405 (3) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—C21 | 1.372 (4) |
C6—C7 | 1.452 (3) | C20—H20 | 0.9300 |
C7—C8 | 1.370 (3) | C21—C22 | 1.382 (4) |
C7—C23 | 1.478 (4) | C21—H21 | 0.9300 |
C8—N1 | 1.415 (3) | C22—H22 | 0.9300 |
C8—C9 | 1.464 (3) | C23—O5 | 1.195 (3) |
C9—C10 | 1.331 (3) | C23—C24 | 1.475 (4) |
C9—H9 | 0.9300 | C25—C24 | 1.523 (4) |
C10—C11 | 1.474 (3) | C25—H25A | 0.9600 |
C10—H10 | 0.9300 | C25—H25B | 0.9600 |
C11—C12 | 1.393 (3) | C25—H25C | 0.9600 |
C11—C16 | 1.397 (3) | N1—S1 | 1.6838 (19) |
C12—C13 | 1.372 (4) | N2—O3 | 1.220 (3) |
C12—H12 | 0.9300 | N2—O4 | 1.224 (3) |
C13—C14 | 1.371 (4) | O1—S1 | 1.4204 (17) |
C13—H13 | 0.9300 | O2—S1 | 1.4198 (17) |
C14—C15 | 1.361 (4) | C24—H24A | 0.9700 |
C14—H14 | 0.9300 | C24—H24B | 0.9700 |
C6—C1—C2 | 123.0 (2) | C11—C16—N2 | 121.6 (2) |
C6—C1—N1 | 107.12 (19) | C22—C17—C18 | 121.2 (2) |
C2—C1—N1 | 129.8 (2) | C22—C17—S1 | 119.64 (17) |
C3—C2—C1 | 116.8 (3) | C18—C17—S1 | 119.14 (17) |
C3—C2—H2 | 121.6 | C19—C18—C17 | 118.7 (2) |
C1—C2—H2 | 121.6 | C19—C18—H18 | 120.6 |
C4—C3—C2 | 121.4 (3) | C17—C18—H18 | 120.6 |
C4—C3—H3 | 119.3 | C20—C19—C18 | 120.3 (2) |
C2—C3—H3 | 119.3 | C20—C19—H19 | 119.8 |
C5—C4—C3 | 121.8 (3) | C18—C19—H19 | 119.8 |
C5—C4—H4 | 119.1 | C21—C20—C19 | 120.7 (2) |
C3—C4—H4 | 119.1 | C21—C20—H20 | 119.6 |
C4—C5—C6 | 118.3 (3) | C19—C20—H20 | 119.6 |
C4—C5—H5 | 120.8 | C20—C21—C22 | 119.8 (2) |
C6—C5—H5 | 120.8 | C20—C21—H21 | 120.1 |
C1—C6—C5 | 118.6 (2) | C22—C21—H21 | 120.1 |
C1—C6—C7 | 108.1 (2) | C17—C22—C21 | 119.2 (2) |
C5—C6—C7 | 133.2 (2) | C17—C22—H22 | 120.4 |
C8—C7—C6 | 107.7 (2) | C21—C22—H22 | 120.4 |
C8—C7—C23 | 130.0 (2) | O5—C23—C24 | 118.4 (3) |
C6—C7—C23 | 122.0 (2) | O5—C23—C7 | 117.3 (3) |
C7—C8—N1 | 108.57 (18) | C24—C23—C7 | 124.2 (2) |
C7—C8—C9 | 130.9 (2) | C24—C25—H25A | 109.5 |
N1—C8—C9 | 120.19 (19) | C24—C25—H25B | 109.5 |
C10—C9—C8 | 124.0 (2) | H25A—C25—H25B | 109.5 |
C10—C9—H9 | 118.0 | C24—C25—H25C | 109.5 |
C8—C9—H9 | 118.0 | H25A—C25—H25C | 109.5 |
C9—C10—C11 | 123.7 (2) | H25B—C25—H25C | 109.5 |
C9—C10—H10 | 118.2 | C8—N1—C1 | 108.36 (18) |
C11—C10—H10 | 118.2 | C8—N1—S1 | 124.61 (14) |
C12—C11—C16 | 115.3 (2) | C1—N1—S1 | 123.06 (16) |
C12—C11—C10 | 119.8 (2) | O3—N2—O4 | 123.5 (3) |
C16—C11—C10 | 124.8 (2) | O3—N2—C16 | 118.7 (2) |
C13—C12—C11 | 122.4 (3) | O4—N2—C16 | 117.8 (2) |
C13—C12—H12 | 118.8 | C23—C24—C25 | 112.9 (2) |
C11—C12—H12 | 118.8 | C23—C24—H24A | 109.0 |
C14—C13—C12 | 120.4 (3) | C25—C24—H24A | 109.0 |
C14—C13—H13 | 119.8 | C23—C24—H24B | 109.0 |
C12—C13—H13 | 119.8 | C25—C24—H24B | 109.0 |
C15—C14—C13 | 119.4 (3) | H24A—C24—H24B | 107.8 |
C15—C14—H14 | 120.3 | O2—S1—O1 | 120.06 (11) |
C13—C14—H14 | 120.3 | O2—S1—N1 | 106.89 (10) |
C14—C15—C16 | 120.0 (3) | O1—S1—N1 | 105.65 (10) |
C14—C15—H15 | 120.0 | O2—S1—C17 | 109.13 (10) |
C16—C15—H15 | 120.0 | O1—S1—C17 | 109.28 (11) |
C15—C16—C11 | 122.4 (2) | N1—S1—C17 | 104.71 (10) |
C15—C16—N2 | 116.0 (2) | ||
C6—C1—C2—C3 | 0.6 (4) | C17—C18—C19—C20 | 0.4 (4) |
N1—C1—C2—C3 | 177.1 (2) | C18—C19—C20—C21 | 0.2 (4) |
C1—C2—C3—C4 | −0.3 (4) | C19—C20—C21—C22 | −0.2 (4) |
C2—C3—C4—C5 | 0.2 (4) | C18—C17—C22—C21 | 1.0 (4) |
C3—C4—C5—C6 | −0.4 (4) | S1—C17—C22—C21 | −178.78 (19) |
C2—C1—C6—C5 | −0.8 (4) | C20—C21—C22—C17 | −0.4 (4) |
N1—C1—C6—C5 | −178.0 (2) | C8—C7—C23—O5 | −167.9 (4) |
C2—C1—C6—C7 | 178.1 (2) | C6—C7—C23—O5 | 4.3 (5) |
N1—C1—C6—C7 | 0.9 (2) | C8—C7—C23—C24 | 8.5 (4) |
C4—C5—C6—C1 | 0.7 (4) | C6—C7—C23—C24 | −179.2 (3) |
C4—C5—C6—C7 | −177.9 (2) | C7—C8—N1—C1 | 3.1 (2) |
C1—C6—C7—C8 | 1.0 (3) | C9—C8—N1—C1 | 177.08 (18) |
C5—C6—C7—C8 | 179.7 (2) | C7—C8—N1—S1 | 161.12 (16) |
C1—C6—C7—C23 | −172.8 (2) | C9—C8—N1—S1 | −24.9 (3) |
C5—C6—C7—C23 | 5.9 (4) | C6—C1—N1—C8 | −2.4 (2) |
C6—C7—C8—N1 | −2.5 (2) | C2—C1—N1—C8 | −179.3 (2) |
C23—C7—C8—N1 | 170.6 (2) | C6—C1—N1—S1 | −160.86 (16) |
C6—C7—C8—C9 | −175.6 (2) | C2—C1—N1—S1 | 22.2 (3) |
C23—C7—C8—C9 | −2.5 (4) | C15—C16—N2—O3 | 152.5 (2) |
C7—C8—C9—C10 | −64.8 (3) | C11—C16—N2—O3 | −26.4 (4) |
N1—C8—C9—C10 | 122.7 (2) | C15—C16—N2—O4 | −26.3 (4) |
C8—C9—C10—C11 | 175.6 (2) | C11—C16—N2—O4 | 154.8 (2) |
C9—C10—C11—C12 | −27.0 (3) | O5—C23—C24—C25 | −4.3 (5) |
C9—C10—C11—C16 | 156.7 (2) | C7—C23—C24—C25 | 179.3 (3) |
C16—C11—C12—C13 | −1.6 (4) | C8—N1—S1—O2 | 36.9 (2) |
C10—C11—C12—C13 | −178.2 (2) | C1—N1—S1—O2 | −168.17 (17) |
C11—C12—C13—C14 | 1.4 (4) | C8—N1—S1—O1 | 165.85 (18) |
C12—C13—C14—C15 | 0.0 (5) | C1—N1—S1—O1 | −39.2 (2) |
C13—C14—C15—C16 | −1.2 (4) | C8—N1—S1—C17 | −78.81 (19) |
C14—C15—C16—C11 | 1.1 (4) | C1—N1—S1—C17 | 76.13 (19) |
C14—C15—C16—N2 | −177.9 (2) | C22—C17—S1—O2 | 159.83 (18) |
C12—C11—C16—C15 | 0.3 (3) | C18—C17—S1—O2 | −20.0 (2) |
C10—C11—C16—C15 | 176.8 (2) | C22—C17—S1—O1 | 26.7 (2) |
C12—C11—C16—N2 | 179.2 (2) | C18—C17—S1—O1 | −153.07 (19) |
C10—C11—C16—N2 | −4.4 (3) | C22—C17—S1—N1 | −86.0 (2) |
C22—C17—C18—C19 | −1.0 (4) | C18—C17—S1—N1 | 94.2 (2) |
S1—C17—C18—C19 | 178.8 (2) |
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Indole derivatives exhibits antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). Some of the indole alkaloids extracted from plants possess interesting cytotoxic and antiparasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981).
The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Umadevi et al., 2013). The phenyl ring makes a dihedral angles of 89.88 (8) and 13.98 (8)° with the indole ring system and the nitro benzene ring, respectively. The sum of bond angles around the atom N1 [356.03°] indicates sp2 hybridized. The molecular structure is stabilized by a weak intramolecular C—H···O interaction.