organic compounds
E)-2-(4-methoxystyryl)-3-methyl-1-phenylsulfonyl-1H-indole
of (aResearch 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, C24H21NO3S, the dihedral angles between the indole ring system (r.m.s. deviation = 0.030 Å) and the sulfur and ethylene-bonded benzene rings are 80.2 (2) and 49.29 (15)°, respectively. The dihedral angle between the pendant benzene rings is 37.7 (2)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and weak C—H⋯π and π–π [centroid-to-centroid distances = 3.549 (2) and 3.743 (3) Å] interactions, forming a three-dimensional network.
Keywords: crystal structure; phenylsulfonyl; 1H-indole; hydrogen bonding; C—H⋯π interactions; π–π interactions.
CCDC reference: 1422542
1. Related literature
For the biological activity of indole derivatives, see: Andreani et al. (2001); Kolocouris et al. (1994). For the structures of related compounds, 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: 1422542
10.1107/S2056989015016631/hb7496sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016631/hb7496Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015016631/hb7496Isup3.cml
To a suspension of sodium hydride (0.22 g, 4.74 mmol) in dry THF (10 ml) at -10°C, the solution of diethyl (3-methyl-1-(phenylsulfonyl)-1H-indol-2-yl)methylphosphonate (1 g, 2.37 mmol) in dry THF (10 ml) was slowly added under nitrogen atmosphere and stirred for 1 h at -10°C. Then, the solution of p-anisaldehyde (0.31 ml, 2.61 mmol) in dry THF (5 ml) was added and the stirring was continued at -10 to 0°C for another 2 h. After completion of the reaction (monitored by TLC), the yellow solution was poured over crushed ice (80 g) containing Conc. HCl (5 ml). The solid obtained was filtered, dried and recrystallized from methanol solution to afford the title compound in the form of 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 = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl. The reflections (2 0 0) and (1 1 0) were omitted during
which were 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. | |
Fig. 2. The crystal packing of the title compound viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1), and C-bound H atoms have been omitted for clarity. |
C24H21NO3S | F(000) = 1696 |
Mr = 403.48 | Dx = 1.306 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5639 reflections |
a = 27.373 (4) Å | θ = 2.6–24.6° |
b = 12.7232 (16) Å | µ = 0.18 mm−1 |
c = 12.0881 (13) Å | T = 295 K |
β = 102.827 (6)° | Block, colourless |
V = 4104.9 (9) Å3 | 0.28 × 0.24 × 0.20 mm |
Z = 8 |
Bruker Kappa APEXII CCD diffractometer | 4852 independent reflections |
Radiation source: fine-focus sealed tube | 2432 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.120 |
ω and φ scan | θmax = 27.9°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −36→35 |
Tmin = 0.951, Tmax = 0.964 | k = −16→16 |
26597 measured reflections | l = −15→15 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.231 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.109P)2 + 3.4059P] where P = (Fo2 + 2Fc2)/3 |
4852 reflections | (Δ/σ)max < 0.001 |
264 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
C24H21NO3S | V = 4104.9 (9) Å3 |
Mr = 403.48 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 27.373 (4) Å | µ = 0.18 mm−1 |
b = 12.7232 (16) Å | T = 295 K |
c = 12.0881 (13) Å | 0.28 × 0.24 × 0.20 mm |
β = 102.827 (6)° |
Bruker Kappa APEXII CCD diffractometer | 4852 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2432 reflections with I > 2σ(I) |
Tmin = 0.951, Tmax = 0.964 | Rint = 0.120 |
26597 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.231 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.28 e Å−3 |
4852 reflections | Δρmin = −0.37 e Å−3 |
264 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 | 0.40832 (12) | 0.0851 (3) | 0.4987 (3) | 0.0558 (9) | |
C2 | 0.44297 (16) | 0.1492 (3) | 0.5659 (4) | 0.0830 (12) | |
H2 | 0.4371 | 0.1778 | 0.6326 | 0.100* | |
C3 | 0.48806 (19) | 0.1704 (4) | 0.5304 (7) | 0.117 (2) | |
H3 | 0.5124 | 0.2133 | 0.5741 | 0.140* | |
C4 | 0.4957 (2) | 0.1274 (5) | 0.4313 (7) | 0.121 (2) | |
H4 | 0.5254 | 0.1412 | 0.4083 | 0.145* | |
C5 | 0.4609 (2) | 0.0657 (5) | 0.3678 (5) | 0.1072 (18) | |
H5 | 0.4667 | 0.0369 | 0.3011 | 0.129* | |
C6 | 0.41692 (15) | 0.0444 (3) | 0.3994 (3) | 0.0697 (10) | |
H6 | 0.3928 | 0.0024 | 0.3536 | 0.084* | |
C7 | 0.30101 (11) | 0.1982 (2) | 0.3861 (3) | 0.0467 (7) | |
C8 | 0.29070 (13) | 0.1401 (3) | 0.2867 (3) | 0.0583 (9) | |
H8 | 0.2952 | 0.0676 | 0.2882 | 0.070* | |
C9 | 0.27364 (14) | 0.1922 (4) | 0.1857 (3) | 0.0712 (11) | |
H9 | 0.2671 | 0.1542 | 0.1183 | 0.085* | |
C10 | 0.26607 (15) | 0.2987 (4) | 0.1820 (3) | 0.0748 (11) | |
H10 | 0.2537 | 0.3314 | 0.1126 | 0.090* | |
C11 | 0.27647 (13) | 0.3574 (3) | 0.2794 (3) | 0.0642 (10) | |
H11 | 0.2713 | 0.4297 | 0.2761 | 0.077* | |
C12 | 0.29493 (11) | 0.3081 (3) | 0.3841 (3) | 0.0496 (8) | |
C13 | 0.31014 (12) | 0.3465 (2) | 0.4972 (3) | 0.0516 (8) | |
C14 | 0.32558 (11) | 0.2641 (2) | 0.5673 (3) | 0.0480 (8) | |
C15 | 0.30517 (15) | 0.4586 (3) | 0.5297 (4) | 0.0736 (11) | |
H15A | 0.3076 | 0.4632 | 0.6100 | 0.110* | |
H15B | 0.2732 | 0.4853 | 0.4902 | 0.110* | |
H15C | 0.3314 | 0.4994 | 0.5097 | 0.110* | |
C16 | 0.34235 (13) | 0.2629 (3) | 0.6895 (3) | 0.0537 (8) | |
H16 | 0.3298 | 0.2110 | 0.7298 | 0.064* | |
C17 | 0.37458 (13) | 0.3316 (3) | 0.7474 (3) | 0.0556 (8) | |
H17 | 0.3887 | 0.3794 | 0.7054 | 0.067* | |
C18 | 0.38995 (12) | 0.3393 (3) | 0.8702 (3) | 0.0534 (8) | |
C19 | 0.42576 (14) | 0.4133 (3) | 0.9200 (3) | 0.0675 (10) | |
H19 | 0.4405 | 0.4553 | 0.8736 | 0.081* | |
C20 | 0.43979 (15) | 0.4256 (3) | 1.0354 (3) | 0.0734 (11) | |
H20 | 0.4635 | 0.4762 | 1.0657 | 0.088* | |
C21 | 0.41924 (13) | 0.3642 (3) | 1.1070 (3) | 0.0619 (9) | |
C22 | 0.38457 (12) | 0.2888 (3) | 1.0604 (3) | 0.0589 (9) | |
H22 | 0.3707 | 0.2457 | 1.1075 | 0.071* | |
C23 | 0.37042 (13) | 0.2769 (3) | 0.9445 (3) | 0.0602 (9) | |
H23 | 0.3470 | 0.2255 | 0.9148 | 0.072* | |
C24 | 0.4123 (2) | 0.3287 (4) | 1.2952 (4) | 0.1073 (17) | |
H24A | 0.3772 | 0.3454 | 1.2805 | 0.161* | |
H24B | 0.4278 | 0.3481 | 1.3717 | 0.161* | |
H24C | 0.4164 | 0.2547 | 1.2852 | 0.161* | |
N1 | 0.31802 (9) | 0.16882 (19) | 0.5006 (2) | 0.0477 (7) | |
O1 | 0.32587 (9) | −0.02048 (17) | 0.4661 (2) | 0.0633 (7) | |
O2 | 0.35975 (11) | 0.0507 (2) | 0.65544 (19) | 0.0733 (8) | |
O3 | 0.43465 (10) | 0.3842 (3) | 1.2199 (2) | 0.0862 (9) | |
S1 | 0.35144 (3) | 0.06038 (6) | 0.53598 (7) | 0.0512 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0529 (19) | 0.0443 (19) | 0.068 (2) | 0.0044 (15) | 0.0089 (17) | 0.0051 (16) |
C2 | 0.071 (3) | 0.058 (3) | 0.112 (3) | 0.002 (2) | 0.005 (2) | −0.013 (2) |
C3 | 0.064 (3) | 0.071 (3) | 0.204 (7) | −0.011 (2) | 0.008 (4) | 0.002 (4) |
C4 | 0.082 (4) | 0.097 (4) | 0.199 (7) | 0.008 (3) | 0.065 (4) | 0.028 (4) |
C5 | 0.088 (3) | 0.114 (4) | 0.138 (5) | 0.007 (3) | 0.064 (3) | 0.021 (4) |
C6 | 0.066 (2) | 0.076 (3) | 0.071 (3) | 0.0089 (19) | 0.0230 (19) | 0.004 (2) |
C7 | 0.0452 (17) | 0.0462 (19) | 0.0502 (19) | 0.0007 (14) | 0.0141 (14) | 0.0035 (15) |
C8 | 0.065 (2) | 0.048 (2) | 0.061 (2) | −0.0047 (16) | 0.0105 (17) | −0.0074 (17) |
C9 | 0.078 (3) | 0.081 (3) | 0.051 (2) | −0.007 (2) | 0.0066 (19) | 0.001 (2) |
C10 | 0.079 (3) | 0.074 (3) | 0.068 (3) | −0.003 (2) | 0.009 (2) | 0.017 (2) |
C11 | 0.063 (2) | 0.053 (2) | 0.076 (3) | 0.0011 (17) | 0.0119 (19) | 0.016 (2) |
C12 | 0.0437 (17) | 0.0437 (19) | 0.063 (2) | 0.0011 (14) | 0.0156 (15) | 0.0046 (16) |
C13 | 0.0476 (18) | 0.0409 (19) | 0.069 (2) | 0.0003 (14) | 0.0194 (16) | −0.0030 (17) |
C14 | 0.0498 (18) | 0.0418 (18) | 0.057 (2) | −0.0044 (14) | 0.0227 (15) | −0.0097 (15) |
C15 | 0.075 (3) | 0.044 (2) | 0.102 (3) | 0.0026 (18) | 0.021 (2) | −0.008 (2) |
C16 | 0.063 (2) | 0.047 (2) | 0.057 (2) | −0.0032 (16) | 0.0262 (17) | −0.0063 (15) |
C17 | 0.059 (2) | 0.053 (2) | 0.056 (2) | −0.0041 (16) | 0.0173 (16) | −0.0039 (16) |
C18 | 0.0542 (19) | 0.046 (2) | 0.062 (2) | −0.0012 (15) | 0.0176 (16) | −0.0080 (16) |
C19 | 0.074 (2) | 0.067 (2) | 0.066 (2) | −0.018 (2) | 0.026 (2) | −0.0078 (19) |
C20 | 0.068 (2) | 0.079 (3) | 0.074 (3) | −0.025 (2) | 0.018 (2) | −0.019 (2) |
C21 | 0.057 (2) | 0.066 (2) | 0.062 (2) | 0.0018 (18) | 0.0109 (18) | −0.0069 (19) |
C22 | 0.057 (2) | 0.057 (2) | 0.063 (2) | −0.0004 (17) | 0.0147 (17) | 0.0087 (18) |
C23 | 0.058 (2) | 0.050 (2) | 0.071 (2) | −0.0051 (16) | 0.0119 (18) | −0.0014 (18) |
C24 | 0.148 (5) | 0.098 (4) | 0.067 (3) | −0.013 (3) | 0.005 (3) | 0.018 (3) |
N1 | 0.0532 (15) | 0.0406 (15) | 0.0509 (16) | −0.0033 (12) | 0.0149 (12) | −0.0032 (12) |
O1 | 0.0731 (16) | 0.0360 (13) | 0.0815 (17) | −0.0048 (11) | 0.0189 (13) | −0.0054 (11) |
O2 | 0.113 (2) | 0.0603 (16) | 0.0497 (15) | 0.0094 (14) | 0.0244 (14) | 0.0132 (12) |
O3 | 0.0832 (19) | 0.109 (2) | 0.0646 (18) | −0.0207 (17) | 0.0131 (15) | −0.0117 (16) |
S1 | 0.0654 (6) | 0.0367 (5) | 0.0536 (5) | 0.0005 (4) | 0.0176 (4) | 0.0033 (4) |
C1—C2 | 1.372 (5) | C14—C16 | 1.447 (4) |
C1—C6 | 1.375 (5) | C15—H15A | 0.9600 |
C1—S1 | 1.742 (4) | C15—H15B | 0.9600 |
C2—C3 | 1.420 (7) | C15—H15C | 0.9600 |
C2—H2 | 0.9300 | C16—C17 | 1.326 (4) |
C3—C4 | 1.375 (8) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C17—C18 | 1.454 (5) |
C4—C5 | 1.337 (8) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C23 | 1.391 (5) |
C5—C6 | 1.369 (6) | C18—C19 | 1.395 (5) |
C5—H5 | 0.9300 | C19—C20 | 1.372 (5) |
C6—H6 | 0.9300 | C19—H19 | 0.9300 |
C7—C8 | 1.386 (4) | C20—C21 | 1.376 (5) |
C7—C12 | 1.407 (5) | C20—H20 | 0.9300 |
C7—N1 | 1.409 (4) | C21—O3 | 1.359 (4) |
C8—C9 | 1.377 (5) | C21—C22 | 1.379 (5) |
C8—H8 | 0.9300 | C22—C23 | 1.377 (5) |
C9—C10 | 1.370 (6) | C22—H22 | 0.9300 |
C9—H9 | 0.9300 | C23—H23 | 0.9300 |
C10—C11 | 1.370 (5) | C24—O3 | 1.396 (5) |
C10—H10 | 0.9300 | C24—H24A | 0.9600 |
C11—C12 | 1.403 (5) | C24—H24B | 0.9600 |
C11—H11 | 0.9300 | C24—H24C | 0.9600 |
C12—C13 | 1.424 (5) | N1—S1 | 1.658 (3) |
C13—C14 | 1.355 (4) | O1—S1 | 1.414 (2) |
C13—C15 | 1.494 (5) | O2—S1 | 1.416 (2) |
C14—N1 | 1.446 (4) | ||
C2—C1—C6 | 120.7 (4) | H15A—C15—H15B | 109.5 |
C2—C1—S1 | 119.6 (3) | C13—C15—H15C | 109.5 |
C6—C1—S1 | 119.6 (3) | H15A—C15—H15C | 109.5 |
C1—C2—C3 | 117.8 (5) | H15B—C15—H15C | 109.5 |
C1—C2—H2 | 121.1 | C17—C16—C14 | 123.7 (3) |
C3—C2—H2 | 121.1 | C17—C16—H16 | 118.2 |
C4—C3—C2 | 120.0 (5) | C14—C16—H16 | 118.2 |
C4—C3—H3 | 120.0 | C16—C17—C18 | 126.3 (3) |
C2—C3—H3 | 120.0 | C16—C17—H17 | 116.9 |
C5—C4—C3 | 120.4 (5) | C18—C17—H17 | 116.9 |
C5—C4—H4 | 119.8 | C23—C18—C19 | 116.1 (3) |
C3—C4—H4 | 119.8 | C23—C18—C17 | 123.7 (3) |
C4—C5—C6 | 121.0 (5) | C19—C18—C17 | 120.2 (3) |
C4—C5—H5 | 119.5 | C20—C19—C18 | 121.8 (3) |
C6—C5—H5 | 119.5 | C20—C19—H19 | 119.1 |
C5—C6—C1 | 120.1 (5) | C18—C19—H19 | 119.1 |
C5—C6—H6 | 120.0 | C19—C20—C21 | 120.9 (4) |
C1—C6—H6 | 120.0 | C19—C20—H20 | 119.5 |
C8—C7—C12 | 121.0 (3) | C21—C20—H20 | 119.5 |
C8—C7—N1 | 132.0 (3) | O3—C21—C20 | 116.5 (3) |
C12—C7—N1 | 107.0 (3) | O3—C21—C22 | 124.9 (3) |
C9—C8—C7 | 118.4 (3) | C20—C21—C22 | 118.6 (3) |
C9—C8—H8 | 120.8 | C23—C22—C21 | 120.3 (3) |
C7—C8—H8 | 120.8 | C23—C22—H22 | 119.9 |
C10—C9—C8 | 121.6 (4) | C21—C22—H22 | 119.9 |
C10—C9—H9 | 119.2 | C22—C23—C18 | 122.2 (3) |
C8—C9—H9 | 119.2 | C22—C23—H23 | 118.9 |
C9—C10—C11 | 120.7 (4) | C18—C23—H23 | 118.9 |
C9—C10—H10 | 119.7 | O3—C24—H24A | 109.5 |
C11—C10—H10 | 119.7 | O3—C24—H24B | 109.5 |
C10—C11—C12 | 119.7 (4) | H24A—C24—H24B | 109.5 |
C10—C11—H11 | 120.2 | O3—C24—H24C | 109.5 |
C12—C11—H11 | 120.2 | H24A—C24—H24C | 109.5 |
C11—C12—C7 | 118.6 (3) | H24B—C24—H24C | 109.5 |
C11—C12—C13 | 133.0 (3) | C7—N1—C14 | 107.5 (2) |
C7—C12—C13 | 108.4 (3) | C7—N1—S1 | 121.2 (2) |
C14—C13—C12 | 108.6 (3) | C14—N1—S1 | 123.5 (2) |
C14—C13—C15 | 127.4 (3) | C21—O3—C24 | 118.4 (3) |
C12—C13—C15 | 123.8 (3) | O1—S1—O2 | 119.45 (15) |
C13—C14—N1 | 108.3 (3) | O1—S1—N1 | 106.24 (14) |
C13—C14—C16 | 129.2 (3) | O2—S1—N1 | 106.86 (14) |
N1—C14—C16 | 122.3 (3) | O1—S1—C1 | 109.21 (16) |
C13—C15—H15A | 109.5 | O2—S1—C1 | 109.19 (17) |
C13—C15—H15B | 109.5 | N1—S1—C1 | 104.87 (14) |
C6—C1—C2—C3 | −1.1 (6) | C23—C18—C19—C20 | −1.8 (5) |
S1—C1—C2—C3 | −177.7 (3) | C17—C18—C19—C20 | 177.5 (3) |
C1—C2—C3—C4 | 0.2 (7) | C18—C19—C20—C21 | 0.7 (6) |
C2—C3—C4—C5 | 0.2 (9) | C19—C20—C21—O3 | −178.4 (4) |
C3—C4—C5—C6 | 0.3 (9) | C19—C20—C21—C22 | 0.8 (6) |
C4—C5—C6—C1 | −1.1 (7) | O3—C21—C22—C23 | 178.1 (3) |
C2—C1—C6—C5 | 1.5 (6) | C20—C21—C22—C23 | −1.1 (5) |
S1—C1—C6—C5 | 178.2 (3) | C21—C22—C23—C18 | −0.1 (5) |
C12—C7—C8—C9 | −0.9 (5) | C19—C18—C23—C22 | 1.5 (5) |
N1—C7—C8—C9 | 179.2 (3) | C17—C18—C23—C22 | −177.7 (3) |
C7—C8—C9—C10 | −1.0 (6) | C8—C7—N1—C14 | 175.9 (3) |
C8—C9—C10—C11 | 1.6 (6) | C12—C7—N1—C14 | −4.0 (3) |
C9—C10—C11—C12 | −0.2 (6) | C8—C7—N1—S1 | 25.9 (4) |
C10—C11—C12—C7 | −1.7 (5) | C12—C7—N1—S1 | −154.0 (2) |
C10—C11—C12—C13 | 178.2 (3) | C13—C14—N1—C7 | 4.5 (3) |
C8—C7—C12—C11 | 2.2 (5) | C16—C14—N1—C7 | 179.0 (3) |
N1—C7—C12—C11 | −177.8 (3) | C13—C14—N1—S1 | 153.6 (2) |
C8—C7—C12—C13 | −177.7 (3) | C16—C14—N1—S1 | −31.8 (4) |
N1—C7—C12—C13 | 2.2 (3) | C20—C21—O3—C24 | 175.7 (4) |
C11—C12—C13—C14 | −179.4 (3) | C22—C21—O3—C24 | −3.5 (6) |
C7—C12—C13—C14 | 0.5 (4) | C7—N1—S1—O1 | −48.0 (3) |
C11—C12—C13—C15 | 5.1 (6) | C14—N1—S1—O1 | 166.9 (2) |
C7—C12—C13—C15 | −175.0 (3) | C7—N1—S1—O2 | −176.6 (2) |
C12—C13—C14—N1 | −3.0 (3) | C14—N1—S1—O2 | 38.3 (3) |
C15—C13—C14—N1 | 172.2 (3) | C7—N1—S1—C1 | 67.6 (3) |
C12—C13—C14—C16 | −177.1 (3) | C14—N1—S1—C1 | −77.5 (3) |
C15—C13—C14—C16 | −1.8 (5) | C2—C1—S1—O1 | −170.2 (3) |
C13—C14—C16—C17 | −45.6 (5) | C6—C1—S1—O1 | 13.1 (3) |
N1—C14—C16—C17 | 141.1 (3) | C2—C1—S1—O2 | −37.9 (3) |
C14—C16—C17—C18 | 175.1 (3) | C6—C1—S1—O2 | 145.3 (3) |
C16—C17—C18—C23 | −3.2 (5) | C2—C1—S1—N1 | 76.3 (3) |
C16—C17—C18—C19 | 177.6 (3) | C6—C1—S1—N1 | −100.4 (3) |
Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C7–C12 and C18–C23 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.93 | 2.46 | 3.249 (5) | 143 |
C15—H15C···Cg4ii | 0.96 | 2.82 | 3.759 (4) | 167 |
C24—H24A···Cg3iii | 0.96 | 2.84 | 3.634 (6) | 140 |
C24—H24C···Cg2iii | 0.96 | 2.88 | 3.520 (5) | 125 |
Symmetry codes: (i) x, −y, z−1/2; (ii) −x+1/2, y+3/2, −z−1/2; (iii) x, y, z+1. |
Cg2, Cg3 and Cg4 are the centroids of the C1–C6, C7–C12 and C18–C23 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.93 | 2.46 | 3.249 (5) | 143 |
C15—H15C···Cg4ii | 0.96 | 2.82 | 3.759 (4) | 167 |
C24—H24A···Cg3iii | 0.96 | 2.84 | 3.634 (6) | 140 |
C24—H24C···Cg2iii | 0.96 | 2.88 | 3.520 (5) | 125 |
Symmetry codes: (i) x, −y, z−1/2; (ii) −x+1/2, y+3/2, −z−1/2; (iii) x, y, z+1. |
Acknowledgements
The authors acknowledge the SAIF, IIT, Madras, for the data collection.
References
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Indole derivatives exhibit antitumour (Andreani et al., 2001) and antiviral (Kolocouris et al., 1994) activities. The molecular structure of the title compound is illustrated in Fig. 1. The geometric parameters of the title molecule agree well with the reported similar structures (Chakkaravarthi et al. 2007, 2008). The torsion angles O1—S1—N1—C7 and O2—S1—N1—C14 [-48.0 (3)° and 38.3 (3)°, respectively] indicate the syn-conformation of the sulfonyl moiety.
In the crystal, the molecules are linked by C—H···O hydrogen bonds (Table 1 & Fig. 2) and the packing also features weak C—H···π (Table 1) and π–π [Cg1···Cg1i distance 3.549 (2) Å; Cg2···Cg2ii distance 3.743 (3) Å; (i) 1/2 - x,1/2 - y,1 - z; 1 - x,-y,1 - z; Cg1 and Cg2 are the centroids of the rings (N1/C7/C12/C13/C14) and (C1—C6), respectively] interactions in a three-dimensional network.