organic compounds
N-{[3-bromo-1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide
ofaResearch and Development Centre, Bharathiar University, Coimbatore 641 046, India, bDepartment of Chemistry, Pallavan College of Engineering, Kanchipuram 631 502, India, cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, dDepartment of Sciences, Chemistry and Materials Research Lab, Amrita Vishwa Vidyapeetham University, Ettimadai, Coimbatore 641 112, India, and eDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
*Correspondence e-mail: ryamuna1@gmail.com, chakkaravarthi_2005@yahoo.com
In the title compound, C21H17BrN2O4S2, the indole ring system subtends dihedral angles of 85.96 (13) and 9.62 (16)° with the planes of the N- and C-bonded benzene rings, respectively. The dihedral angles between the benzene rings is 88.05 (17)°. The molecular conformation is stabilized by intramolecular N—H⋯O and C—H⋯O hydrogen bonds and an aromatic π–π stacking [centroid-to-centroid distance = 3.503 (2) Å] interaction. In the crystal, short Br⋯O [2.9888 (18) Å] contacts link the molecules into [010] chains. The chains are cross-linked by weak C—H⋯π interactions, forming a three-dimensional network.
Keywords: crystal structure; benzenesulfonamide; phenylsulfonyl; biological activity; derivatives; hydrogen bonding; C—H⋯π interactions.
CCDC reference: 1423139
1. Related literature
For the biological activity of indole derivatives, see: Andreani et al. (2001); Andreev et al. (2015); Kolocouris et al. (1994). For related structures, see: Chakkaravarthi et al. (2007, 2008).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); 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 and PLATON.
Supporting information
CCDC reference: 1423139
10.1107/S2056989015016874/hb7501sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016874/hb7501Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015016874/hb7501Isup3.cml
To a solution of 3-bromo-2-(bromomethyl)-1-(phenylsulfonyl)-1H-indole (0.5 g, 1.16 mmol) in acetonitrile (10 ml) was added K2CO3 (0.32 g, 2.33 mmol) and benzenesulphonamide (0.23 g, 1.51 mmol). The reaction mixture was then stirred at reflux for 12 h. After completion of the reaction (monitored by TLC), it was cooled to room temperature and reaction mass was poured over crushed ice (30 g). The solid obtained was filtered and dried. The crude product was recrystallized from methanol to afford the title compound as colourless blocks.
H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for C—H and C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2. H atom for N atom is fixed from Fourier map and refined freely with distance restraint of 0.88 (1) Å. The reflection (0 1 1) is omitted during
which is owing poor agreement.Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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) and PLATON (Spek, 2009).Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms. |
C21H17BrN2O4S2 | F(000) = 1024 |
Mr = 505.40 | Dx = 1.609 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7461 reflections |
a = 7.5129 (6) Å | θ = 2.3–24.4° |
b = 17.4245 (14) Å | µ = 2.20 mm−1 |
c = 16.0988 (14) Å | T = 295 K |
β = 98.087 (3)° | Block, colourless |
V = 2086.5 (3) Å3 | 0.28 × 0.24 × 0.22 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 3808 independent reflections |
Radiation source: fine-focus sealed tube | 2942 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω and φ scan | θmax = 25.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→8 |
Tmin = 0.578, Tmax = 0.643 | k = −20→20 |
23680 measured reflections | l = −19→19 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.055P)2 + 0.8751P] where P = (Fo2 + 2Fc2)/3 |
3808 reflections | (Δ/σ)max < 0.001 |
275 parameters | Δρmax = 0.60 e Å−3 |
1 restraint | Δρmin = −0.40 e Å−3 |
C21H17BrN2O4S2 | V = 2086.5 (3) Å3 |
Mr = 505.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.5129 (6) Å | µ = 2.20 mm−1 |
b = 17.4245 (14) Å | T = 295 K |
c = 16.0988 (14) Å | 0.28 × 0.24 × 0.22 mm |
β = 98.087 (3)° |
Bruker Kappa APEXII CCD diffractometer | 3808 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2942 reflections with I > 2σ(I) |
Tmin = 0.578, Tmax = 0.643 | Rint = 0.042 |
23680 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 1 restraint |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.60 e Å−3 |
3808 reflections | Δρmin = −0.40 e Å−3 |
275 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2432 (4) | 0.19281 (14) | 0.09825 (16) | 0.0381 (6) | |
C2 | 0.1728 (4) | 0.25496 (16) | 0.13721 (19) | 0.0481 (7) | |
H2 | 0.2437 | 0.2827 | 0.1788 | 0.058* | |
C3 | −0.0038 (4) | 0.27433 (19) | 0.1127 (2) | 0.0594 (8) | |
H3 | −0.0543 | 0.3151 | 0.1384 | 0.071* | |
C4 | −0.1065 (4) | 0.2335 (2) | 0.0501 (2) | 0.0611 (9) | |
H4 | −0.2255 | 0.2476 | 0.0332 | 0.073* | |
C5 | −0.0355 (4) | 0.1724 (2) | 0.0126 (2) | 0.0601 (8) | |
H5 | −0.1065 | 0.1450 | −0.0293 | 0.072* | |
C6 | 0.1410 (4) | 0.15136 (17) | 0.03663 (18) | 0.0498 (7) | |
H6 | 0.1900 | 0.1098 | 0.0115 | 0.060* | |
C7 | 0.4610 (4) | 0.02955 (14) | 0.20280 (17) | 0.0396 (6) | |
C8 | 0.4202 (4) | 0.00661 (15) | 0.27698 (19) | 0.0460 (7) | |
C9 | 0.4154 (4) | 0.07015 (17) | 0.33242 (18) | 0.0453 (7) | |
C10 | 0.3906 (5) | 0.0770 (2) | 0.4160 (2) | 0.0625 (9) | |
H10 | 0.3682 | 0.0340 | 0.4471 | 0.075* | |
C11 | 0.4000 (5) | 0.1484 (3) | 0.4513 (2) | 0.0736 (11) | |
H11 | 0.3829 | 0.1540 | 0.5071 | 0.088* | |
C12 | 0.4344 (5) | 0.2125 (2) | 0.4059 (2) | 0.0692 (10) | |
H12 | 0.4376 | 0.2605 | 0.4314 | 0.083* | |
C13 | 0.4638 (4) | 0.20715 (18) | 0.32402 (18) | 0.0544 (8) | |
H13 | 0.4891 | 0.2503 | 0.2938 | 0.065* | |
C14 | 0.4545 (4) | 0.13474 (16) | 0.28803 (16) | 0.0408 (6) | |
C15 | 0.5031 (4) | −0.01861 (16) | 0.13068 (18) | 0.0494 (7) | |
H15A | 0.4799 | −0.0719 | 0.1430 | 0.059* | |
H15B | 0.4206 | −0.0045 | 0.0812 | 0.059* | |
N2 | 0.6852 (4) | −0.01280 (14) | 0.11069 (15) | 0.0499 (6) | |
C16 | 0.8919 (4) | 0.02153 (17) | 0.26010 (18) | 0.0480 (7) | |
C17 | 0.8597 (5) | −0.0015 (2) | 0.3376 (2) | 0.0676 (9) | |
H17 | 0.8240 | −0.0515 | 0.3468 | 0.081* | |
C18 | 0.8818 (6) | 0.0519 (4) | 0.4024 (2) | 0.0907 (15) | |
H18 | 0.8611 | 0.0378 | 0.4559 | 0.109* | |
C19 | 0.9337 (6) | 0.1249 (3) | 0.3874 (3) | 0.0932 (15) | |
H19 | 0.9473 | 0.1604 | 0.4310 | 0.112* | |
C20 | 0.9656 (6) | 0.1467 (2) | 0.3107 (3) | 0.0802 (11) | |
H20 | 1.0023 | 0.1966 | 0.3017 | 0.096* | |
C21 | 0.9440 (5) | 0.09537 (18) | 0.2461 (2) | 0.0615 (9) | |
H21 | 0.9645 | 0.1103 | 0.1928 | 0.074* | |
N1 | 0.4842 (3) | 0.11047 (11) | 0.20700 (13) | 0.0390 (5) | |
O1 | 0.5276 (3) | 0.12773 (11) | 0.05899 (11) | 0.0453 (5) | |
O2 | 0.5650 (3) | 0.23686 (10) | 0.15614 (13) | 0.0495 (5) | |
O3 | 1.0073 (3) | −0.03343 (15) | 0.12907 (15) | 0.0726 (7) | |
O4 | 0.8142 (4) | −0.11538 (13) | 0.20432 (18) | 0.0801 (8) | |
S1 | 0.47029 (9) | 0.16993 (3) | 0.12591 (4) | 0.03756 (17) | |
S2 | 0.85938 (11) | −0.04228 (4) | 0.17424 (5) | 0.0547 (2) | |
Br1 | 0.39126 (5) | −0.095232 (19) | 0.30887 (3) | 0.07287 (16) | |
H2A | 0.709 (4) | 0.0315 (11) | 0.0891 (19) | 0.063 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0491 (15) | 0.0309 (13) | 0.0358 (14) | 0.0022 (11) | 0.0105 (12) | 0.0067 (11) |
C2 | 0.0550 (18) | 0.0405 (15) | 0.0503 (17) | 0.0039 (13) | 0.0131 (14) | −0.0015 (13) |
C3 | 0.060 (2) | 0.0540 (19) | 0.068 (2) | 0.0136 (15) | 0.0194 (17) | 0.0043 (16) |
C4 | 0.0473 (18) | 0.074 (2) | 0.063 (2) | 0.0076 (16) | 0.0136 (16) | 0.0215 (18) |
C5 | 0.057 (2) | 0.070 (2) | 0.0511 (19) | −0.0028 (16) | −0.0004 (15) | 0.0005 (16) |
C6 | 0.0585 (18) | 0.0481 (16) | 0.0429 (16) | 0.0051 (14) | 0.0071 (14) | −0.0033 (13) |
C7 | 0.0458 (15) | 0.0278 (13) | 0.0426 (16) | 0.0014 (11) | −0.0027 (12) | −0.0019 (11) |
C8 | 0.0471 (16) | 0.0343 (14) | 0.0553 (18) | 0.0013 (12) | 0.0029 (13) | 0.0114 (13) |
C9 | 0.0449 (16) | 0.0508 (16) | 0.0395 (16) | 0.0082 (13) | 0.0032 (12) | 0.0066 (13) |
C10 | 0.060 (2) | 0.083 (2) | 0.0459 (19) | 0.0155 (18) | 0.0124 (15) | 0.0165 (17) |
C11 | 0.082 (3) | 0.103 (3) | 0.0357 (18) | 0.020 (2) | 0.0081 (17) | −0.011 (2) |
C12 | 0.084 (2) | 0.075 (2) | 0.047 (2) | 0.0125 (19) | 0.0021 (17) | −0.0225 (18) |
C13 | 0.071 (2) | 0.0479 (17) | 0.0427 (17) | 0.0051 (15) | 0.0013 (14) | −0.0102 (14) |
C14 | 0.0477 (15) | 0.0429 (15) | 0.0305 (14) | 0.0059 (12) | 0.0016 (12) | −0.0033 (12) |
C15 | 0.066 (2) | 0.0318 (14) | 0.0467 (17) | −0.0015 (13) | −0.0036 (14) | −0.0077 (12) |
N2 | 0.0670 (17) | 0.0384 (13) | 0.0434 (14) | 0.0101 (12) | 0.0046 (12) | −0.0085 (11) |
C16 | 0.0510 (17) | 0.0538 (17) | 0.0376 (16) | 0.0071 (14) | 0.0004 (13) | −0.0008 (13) |
C17 | 0.064 (2) | 0.087 (3) | 0.050 (2) | 0.0044 (19) | 0.0009 (16) | 0.0105 (19) |
C18 | 0.070 (3) | 0.165 (5) | 0.036 (2) | 0.011 (3) | 0.0040 (17) | −0.011 (3) |
C19 | 0.069 (3) | 0.130 (4) | 0.076 (3) | 0.009 (3) | −0.004 (2) | −0.053 (3) |
C20 | 0.082 (3) | 0.079 (3) | 0.077 (3) | −0.003 (2) | −0.002 (2) | −0.030 (2) |
C21 | 0.073 (2) | 0.057 (2) | 0.054 (2) | 0.0000 (16) | 0.0075 (17) | −0.0085 (16) |
N1 | 0.0539 (14) | 0.0284 (11) | 0.0333 (12) | 0.0019 (9) | 0.0017 (10) | −0.0019 (9) |
O1 | 0.0563 (12) | 0.0433 (10) | 0.0378 (11) | 0.0081 (9) | 0.0116 (9) | 0.0007 (8) |
O2 | 0.0572 (12) | 0.0313 (9) | 0.0611 (13) | −0.0067 (8) | 0.0115 (10) | −0.0007 (9) |
O3 | 0.0705 (15) | 0.0824 (17) | 0.0664 (15) | 0.0217 (13) | 0.0144 (12) | −0.0178 (13) |
O4 | 0.103 (2) | 0.0382 (12) | 0.0928 (19) | 0.0131 (12) | −0.0088 (15) | 0.0084 (12) |
S1 | 0.0483 (4) | 0.0282 (3) | 0.0369 (4) | 0.0012 (3) | 0.0085 (3) | 0.0019 (3) |
S2 | 0.0689 (5) | 0.0416 (4) | 0.0516 (5) | 0.0154 (4) | 0.0018 (4) | −0.0060 (3) |
Br1 | 0.0843 (3) | 0.0436 (2) | 0.0925 (3) | −0.00243 (16) | 0.0188 (2) | 0.02590 (17) |
C1—C6 | 1.371 (4) | C13—C14 | 1.386 (4) |
C1—C2 | 1.393 (4) | C13—H13 | 0.9300 |
C1—S1 | 1.748 (3) | C14—N1 | 1.418 (3) |
C2—C3 | 1.372 (4) | C15—N2 | 1.453 (4) |
C2—H2 | 0.9300 | C15—H15A | 0.9700 |
C3—C4 | 1.377 (5) | C15—H15B | 0.9700 |
C3—H3 | 0.9300 | N2—S2 | 1.627 (3) |
C4—C5 | 1.369 (5) | N2—H2A | 0.874 (10) |
C4—H4 | 0.9300 | C16—C17 | 1.364 (5) |
C5—C6 | 1.378 (4) | C16—C21 | 1.373 (4) |
C5—H5 | 0.9300 | C16—S2 | 1.764 (3) |
C6—H6 | 0.9300 | C17—C18 | 1.391 (6) |
C7—C8 | 1.336 (4) | C17—H17 | 0.9300 |
C7—N1 | 1.421 (3) | C18—C19 | 1.361 (7) |
C7—C15 | 1.502 (4) | C18—H18 | 0.9300 |
C8—C9 | 1.426 (4) | C19—C20 | 1.346 (7) |
C8—Br1 | 1.868 (3) | C19—H19 | 0.9300 |
C9—C14 | 1.387 (4) | C20—C21 | 1.363 (5) |
C9—C10 | 1.388 (4) | C20—H20 | 0.9300 |
C10—C11 | 1.367 (5) | C21—H21 | 0.9300 |
C10—H10 | 0.9300 | N1—S1 | 1.659 (2) |
C11—C12 | 1.380 (5) | O1—S1 | 1.4203 (19) |
C11—H11 | 0.9300 | O2—S1 | 1.416 (2) |
C12—C13 | 1.370 (4) | O3—S2 | 1.419 (3) |
C12—H12 | 0.9300 | O4—S2 | 1.421 (3) |
C6—C1—C2 | 121.7 (3) | N2—C15—C7 | 116.1 (2) |
C6—C1—S1 | 119.4 (2) | N2—C15—H15A | 108.3 |
C2—C1—S1 | 118.8 (2) | C7—C15—H15A | 108.3 |
C3—C2—C1 | 118.4 (3) | N2—C15—H15B | 108.3 |
C3—C2—H2 | 120.8 | C7—C15—H15B | 108.3 |
C1—C2—H2 | 120.8 | H15A—C15—H15B | 107.4 |
C2—C3—C4 | 120.2 (3) | C15—N2—S2 | 122.6 (2) |
C2—C3—H3 | 119.9 | C15—N2—H2A | 113 (2) |
C4—C3—H3 | 119.9 | S2—N2—H2A | 110 (2) |
C5—C4—C3 | 120.7 (3) | C17—C16—C21 | 121.1 (3) |
C5—C4—H4 | 119.6 | C17—C16—S2 | 120.6 (3) |
C3—C4—H4 | 119.6 | C21—C16—S2 | 118.3 (2) |
C4—C5—C6 | 120.2 (3) | C16—C17—C18 | 118.1 (4) |
C4—C5—H5 | 119.9 | C16—C17—H17 | 121.0 |
C6—C5—H5 | 119.9 | C18—C17—H17 | 121.0 |
C1—C6—C5 | 118.8 (3) | C19—C18—C17 | 120.0 (4) |
C1—C6—H6 | 120.6 | C19—C18—H18 | 120.0 |
C5—C6—H6 | 120.6 | C17—C18—H18 | 120.0 |
C8—C7—N1 | 107.2 (2) | C20—C19—C18 | 121.2 (4) |
C8—C7—C15 | 128.6 (2) | C20—C19—H19 | 119.4 |
N1—C7—C15 | 123.6 (2) | C18—C19—H19 | 119.4 |
C7—C8—C9 | 110.9 (2) | C19—C20—C21 | 119.9 (4) |
C7—C8—Br1 | 125.5 (2) | C19—C20—H20 | 120.1 |
C9—C8—Br1 | 123.5 (2) | C21—C20—H20 | 120.1 |
C14—C9—C10 | 119.8 (3) | C20—C21—C16 | 119.7 (4) |
C14—C9—C8 | 106.4 (2) | C20—C21—H21 | 120.1 |
C10—C9—C8 | 133.7 (3) | C16—C21—H21 | 120.1 |
C11—C10—C9 | 118.4 (3) | C14—N1—C7 | 107.8 (2) |
C11—C10—H10 | 120.8 | C14—N1—S1 | 122.48 (17) |
C9—C10—H10 | 120.8 | C7—N1—S1 | 126.06 (17) |
C10—C11—C12 | 121.3 (3) | O2—S1—O1 | 119.71 (12) |
C10—C11—H11 | 119.4 | O2—S1—N1 | 105.73 (12) |
C12—C11—H11 | 119.4 | O1—S1—N1 | 106.35 (11) |
C13—C12—C11 | 121.5 (3) | O2—S1—C1 | 108.96 (12) |
C13—C12—H12 | 119.3 | O1—S1—C1 | 108.32 (12) |
C11—C12—H12 | 119.3 | N1—S1—C1 | 107.10 (12) |
C12—C13—C14 | 117.3 (3) | O3—S2—O4 | 120.92 (16) |
C12—C13—H13 | 121.3 | O3—S2—N2 | 105.18 (15) |
C14—C13—H13 | 121.3 | O4—S2—N2 | 106.73 (15) |
C13—C14—C9 | 121.7 (3) | O3—S2—C16 | 107.51 (15) |
C13—C14—N1 | 130.6 (3) | O4—S2—C16 | 108.14 (16) |
C9—C14—N1 | 107.7 (2) | N2—S2—C16 | 107.71 (13) |
C6—C1—C2—C3 | 0.2 (4) | C18—C19—C20—C21 | 0.8 (7) |
S1—C1—C2—C3 | 177.5 (2) | C19—C20—C21—C16 | −0.8 (6) |
C1—C2—C3—C4 | −1.0 (5) | C17—C16—C21—C20 | 0.5 (5) |
C2—C3—C4—C5 | 1.2 (5) | S2—C16—C21—C20 | 178.2 (3) |
C3—C4—C5—C6 | −0.5 (5) | C13—C14—N1—C7 | 178.7 (3) |
C2—C1—C6—C5 | 0.4 (4) | C9—C14—N1—C7 | 0.4 (3) |
S1—C1—C6—C5 | −176.9 (2) | C13—C14—N1—S1 | −21.7 (4) |
C4—C5—C6—C1 | −0.3 (5) | C9—C14—N1—S1 | 159.99 (19) |
N1—C7—C8—C9 | −0.2 (3) | C8—C7—N1—C14 | −0.1 (3) |
C15—C7—C8—C9 | 171.5 (3) | C15—C7—N1—C14 | −172.3 (2) |
N1—C7—C8—Br1 | −175.46 (19) | C8—C7—N1—S1 | −158.8 (2) |
C15—C7—C8—Br1 | −3.8 (4) | C15—C7—N1—S1 | 29.0 (4) |
C7—C8—C9—C14 | 0.5 (3) | C14—N1—S1—O2 | 45.3 (2) |
Br1—C8—C9—C14 | 175.8 (2) | C7—N1—S1—O2 | −158.9 (2) |
C7—C8—C9—C10 | −175.7 (3) | C14—N1—S1—O1 | 173.6 (2) |
Br1—C8—C9—C10 | −0.3 (5) | C7—N1—S1—O1 | −30.7 (3) |
C14—C9—C10—C11 | 2.1 (5) | C14—N1—S1—C1 | −70.8 (2) |
C8—C9—C10—C11 | 177.8 (3) | C7—N1—S1—C1 | 85.0 (2) |
C9—C10—C11—C12 | −0.4 (5) | C6—C1—S1—O2 | 151.8 (2) |
C10—C11—C12—C13 | −1.2 (6) | C2—C1—S1—O2 | −25.6 (2) |
C11—C12—C13—C14 | 1.2 (5) | C6—C1—S1—O1 | 20.0 (3) |
C12—C13—C14—C9 | 0.6 (4) | C2—C1—S1—O1 | −157.4 (2) |
C12—C13—C14—N1 | −177.5 (3) | C6—C1—S1—N1 | −94.3 (2) |
C10—C9—C14—C13 | −2.2 (4) | C2—C1—S1—N1 | 88.3 (2) |
C8—C9—C14—C13 | −179.0 (3) | C15—N2—S2—O3 | 174.6 (2) |
C10—C9—C14—N1 | 176.3 (3) | C15—N2—S2—O4 | 45.0 (3) |
C8—C9—C14—N1 | −0.5 (3) | C15—N2—S2—C16 | −70.9 (2) |
C8—C7—C15—N2 | −114.1 (3) | C17—C16—S2—O3 | −136.9 (3) |
N1—C7—C15—N2 | 56.3 (4) | C21—C16—S2—O3 | 45.3 (3) |
C7—C15—N2—S2 | 66.0 (3) | C17—C16—S2—O4 | −4.8 (3) |
C21—C16—C17—C18 | −0.2 (5) | C21—C16—S2—O4 | 177.4 (3) |
S2—C16—C17—C18 | −177.9 (3) | C17—C16—S2—N2 | 110.2 (3) |
C16—C17—C18—C19 | 0.2 (6) | C21—C16—S2—N2 | −67.5 (3) |
C17—C18—C19—C20 | −0.5 (7) |
Cg2 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.87 (1) | 2.17 (3) | 2.795 (3) | 128 (3) |
C13—H13···O2 | 0.93 | 2.38 | 2.954 (4) | 120 |
C21—H21···Cg2i | 0.93 | 2.81 | 3.667 (3) | 155 |
Symmetry code: (i) x+1, y, z. |
Cg2 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.874 (10) | 2.17 (3) | 2.795 (3) | 128 (3) |
C13—H13···O2 | 0.93 | 2.38 | 2.954 (4) | 120 |
C21—H21···Cg2i | 0.93 | 2.81 | 3.667 (3) | 155 |
Symmetry code: (i) x+1, y, z. |
Acknowledgements
The authors acknowledge the SAIF, IIT, Madras, for the data collection.
References
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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 are known to exhibit activities such as antitumour (Andreani et al., 2001); anti-hepatitis C virus (Andreev et al., 2015) and antiviral (Kolocouris et al., 1994). We herein report the crystal structure of (I). The ORTEP diagram of the title compound (I) is shown in Fig. 1. The geometric parameters of (I) are comparable with the reported similar structures (Chakkaravarthi et al. 2007, 2008). The phenyl rings (C1—C6) and (C16—C21) form the dihedral angles of 85.96 (13)° and 9.62 (16)°, respectively with the indole ring system. The phenyl rings (C1—C6) and (C16—C21) are orthogonal to each other, with the dihedral angle of 88.05 (17)°.
The molecular structure (Fig. 1) is stabilized by weak intramolecular N—H···O, C—H···O and C—H···Br hydrogen bonds (Table 1) and π–π [centroid-to-centroid distance = 3.503 (2) Å] interaction. In the crystal structure, the intermolecular weak Br···O [Br1···O2i and O2··· Br1ii contacts at 2.99 Å; (i) (1 - x,-1/2 + y,1/2 - z); (ii) 1 - x,1/2 + y,1/2 - z)] contacts form the molecules into infinite one-dimensional chain along [0 1 0] and these chains are further influenced by weak C—H···π interactions (Table 1) to form a three dimensional network.