Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045369/is2208sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045369/is2208Isup2.hkl |
CCDC reference: 663819
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.126
- Data-to-parameter ratio = 21.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Harris & Uhle (1960); Ho et al. (1986); Karali et al. (2007); Palani et al. (2006a,b); Ragno et al. (2006); Stevenson et al. (2000).
1-Phenylsulfonyl-3-methyl-2-bromomethylindole (2 g, 5.49 mmol) was dissolved in dry CH3CN (20 ml). To this anisole (0.89 ml, 8.23 mmol), ZnBr2 (2.47 g, 10.96 mmol) were added and refluxed for 24 h. The reaction mixture was quenched with ice containing few drops of conc. HCl, extracted with CHCl3 (3 × 5 ml) and dried Na2SO4. The solvent was removed under vacuo. Then crude was recrystallized from 5% ethyl acetate / hexane (5:95) to get the diffraction quality crystals.
The H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.98 Å, and with Uiso= 1.5Ueq(C) for methyl H and 1.2Ueq(C) for other H.
Indole compounds are used as bioactive drugs (Stevenson et al., 2000). The indole derivatives exhibit antituberculosis (Karali et al., 2007), anti-HIV (Ragno et al., 2006), central nervous system depressant and muscle relaxant properties (Harris & Uhle, 1960; Ho et al., 1986). Herein, we report the crystal structure of the title compound, (I).
In the molecule, the planar sulfonyl bound phenyl group subtends an angle of 77.7 (1)° with the planar indole moiety. The methyl atom is deviated from the indole ring by 0.075 (3) Å. The bond lengths and bond angles in the molecule are comparable with the values reported in literature (Palani et al., 2006a,b). The methoxy group also lies in the plane of the benzyl ring. The methoxybenzyl group is oriented at angle of 80.1 (1)° with respect to the indole moiety. The geometry around S1 is distorted from tetrahedral values. The widening of the angle (O1—S1—O2=) 119.46 (8)° and narrowing of the angle (N1—S1—C9=) 105.19 (6)° are due to the electon withdrawing character of the phenyl sulfonyl group. The sum of the bond angle around N1 indicates that the atom is in an sp2 hybridized state.
A few C—H···O intramolecular interactions play the role to stabilize the molecules in addition to a C—H···π interaction (Table 1). The molecules in the unit cell are packed by van der Waals forces.
For related literature, see: Harris & Uhle (1960); Ho et al. (1986); Karali et al. (2007); Palani et al. (2006a,b); Ragno et al. (2006); Stevenson et al. (2000).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).
C23H21NO3S | Z = 2 |
Mr = 391.47 | F(000) = 412 |
Triclinic, P1 | Dx = 1.298 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2518 (3) Å | Cell parameters from 14224 reflections |
b = 10.0817 (4) Å | θ = 2.0–27.5° |
c = 12.8169 (5) Å | µ = 0.19 mm−1 |
α = 97.244 (2)° | T = 293 K |
β = 97.876 (2)° | Needle, colourless |
γ = 105.709 (2)° | 0.24 × 0.20 × 0.18 mm |
V = 1001.76 (7) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 4234 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 29.2°, θmin = 1.6° |
ω scans | h = −11→11 |
23750 measured reflections | k = −13→13 |
5432 independent reflections | l = −17→17 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0596P)2 + 0.1977P] where P = (Fo2 + 2Fc2)/3 |
5432 reflections | (Δ/σ)max < 0.001 |
254 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C23H21NO3S | γ = 105.709 (2)° |
Mr = 391.47 | V = 1001.76 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.2518 (3) Å | Mo Kα radiation |
b = 10.0817 (4) Å | µ = 0.19 mm−1 |
c = 12.8169 (5) Å | T = 293 K |
α = 97.244 (2)° | 0.24 × 0.20 × 0.18 mm |
β = 97.876 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 4234 reflections with I > 2σ(I) |
23750 measured reflections | Rint = 0.024 |
5432 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.26 e Å−3 |
5432 reflections | Δρmin = −0.26 e Å−3 |
254 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 | ||
S1 | 0.36424 (4) | 0.91092 (4) | 0.76283 (3) | 0.05054 (12) | |
N1 | 0.37371 (14) | 0.75504 (11) | 0.70911 (9) | 0.0427 (2) | |
O1 | 0.46782 (14) | 1.00993 (11) | 0.71146 (12) | 0.0716 (4) | |
O2 | 0.40232 (17) | 0.92234 (13) | 0.87515 (10) | 0.0754 (4) | |
O3 | 1.06112 (15) | 0.70612 (13) | 1.03001 (10) | 0.0685 (3) | |
C1 | 0.32438 (17) | 0.63013 (14) | 0.75472 (11) | 0.0463 (3) | |
C2 | 0.2657 (2) | 0.51995 (16) | 0.67479 (14) | 0.0604 (4) | |
C3 | 0.2704 (2) | 0.56945 (17) | 0.57476 (13) | 0.0593 (4) | |
C4 | 0.33517 (17) | 0.71415 (15) | 0.59622 (11) | 0.0469 (3) | |
C5 | 0.3562 (2) | 0.7930 (2) | 0.51567 (14) | 0.0644 (4) | |
H5 | 0.3989 | 0.8900 | 0.5307 | 0.077* | |
C6 | 0.3111 (3) | 0.7213 (3) | 0.41179 (16) | 0.0882 (7) | |
H6 | 0.3242 | 0.7712 | 0.3557 | 0.106* | |
C7 | 0.2472 (4) | 0.5779 (3) | 0.38937 (17) | 0.1049 (8) | |
H7 | 0.2180 | 0.5329 | 0.3186 | 0.126* | |
C8 | 0.2258 (3) | 0.5004 (2) | 0.46920 (17) | 0.0933 (7) | |
H8 | 0.1823 | 0.4035 | 0.4534 | 0.112* | |
C9 | 0.15053 (16) | 0.90762 (13) | 0.72524 (11) | 0.0431 (3) | |
C10 | 0.1117 (2) | 0.99273 (17) | 0.65585 (14) | 0.0581 (4) | |
H10 | 0.1972 | 1.0499 | 0.6275 | 0.070* | |
C11 | −0.0566 (2) | 0.9916 (2) | 0.62901 (15) | 0.0691 (5) | |
H11 | −0.0848 | 1.0496 | 0.5831 | 0.083* | |
C12 | −0.1822 (2) | 0.9055 (2) | 0.66976 (15) | 0.0659 (4) | |
H12 | −0.2955 | 0.9041 | 0.6504 | 0.079* | |
C13 | −0.1415 (2) | 0.8215 (2) | 0.73890 (16) | 0.0681 (5) | |
H13 | −0.2274 | 0.7637 | 0.7666 | 0.082* | |
C14 | 0.0248 (2) | 0.82196 (18) | 0.76742 (14) | 0.0585 (4) | |
H14 | 0.0526 | 0.7653 | 0.8146 | 0.070* | |
C15 | 0.35876 (19) | 0.62830 (19) | 0.87222 (12) | 0.0560 (4) | |
H15A | 0.2936 | 0.5385 | 0.8858 | 0.067* | |
H15B | 0.3190 | 0.6998 | 0.9095 | 0.067* | |
C16 | 0.54654 (18) | 0.65305 (16) | 0.91723 (10) | 0.0475 (3) | |
C17 | 0.6286 (2) | 0.55505 (15) | 0.88721 (12) | 0.0515 (3) | |
H17 | 0.5673 | 0.4739 | 0.8394 | 0.062* | |
C18 | 0.7990 (2) | 0.57510 (15) | 0.92664 (12) | 0.0534 (3) | |
H18 | 0.8513 | 0.5078 | 0.9053 | 0.064* | |
C19 | 0.89245 (19) | 0.69517 (15) | 0.99790 (11) | 0.0491 (3) | |
C20 | 0.8126 (2) | 0.79269 (17) | 1.03037 (12) | 0.0586 (4) | |
H20 | 0.8734 | 0.8730 | 1.0792 | 0.070* | |
C21 | 0.6407 (2) | 0.77048 (18) | 0.98990 (12) | 0.0586 (4) | |
H21 | 0.5876 | 0.8367 | 1.0125 | 0.070* | |
C22 | 1.1655 (3) | 0.8269 (2) | 1.10098 (18) | 0.0878 (6) | |
H22A | 1.2799 | 0.8202 | 1.1164 | 0.132* | |
H22B | 1.1209 | 0.8347 | 1.1661 | 0.132* | |
H22C | 1.1667 | 0.9080 | 1.0687 | 0.132* | |
C23 | 0.2103 (4) | 0.3676 (2) | 0.6834 (2) | 0.1025 (8) | |
H23A | 0.2918 | 0.3238 | 0.6598 | 0.154* | |
H23B | 0.0999 | 0.3233 | 0.6395 | 0.154* | |
H23C | 0.2038 | 0.3582 | 0.7565 | 0.154* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.04216 (18) | 0.04139 (19) | 0.0631 (2) | 0.01361 (14) | −0.00070 (15) | −0.00118 (15) |
N1 | 0.0429 (5) | 0.0413 (6) | 0.0453 (6) | 0.0153 (4) | 0.0078 (4) | 0.0064 (4) |
O1 | 0.0431 (5) | 0.0430 (6) | 0.1228 (11) | 0.0036 (4) | 0.0136 (6) | 0.0136 (6) |
O2 | 0.0846 (8) | 0.0748 (8) | 0.0606 (7) | 0.0414 (7) | −0.0173 (6) | −0.0175 (6) |
O3 | 0.0590 (6) | 0.0716 (8) | 0.0720 (7) | 0.0274 (6) | −0.0035 (5) | 0.0002 (6) |
C1 | 0.0425 (6) | 0.0470 (7) | 0.0518 (7) | 0.0139 (6) | 0.0107 (5) | 0.0135 (6) |
C2 | 0.0661 (9) | 0.0444 (8) | 0.0640 (9) | 0.0080 (7) | 0.0052 (7) | 0.0098 (7) |
C3 | 0.0663 (9) | 0.0534 (9) | 0.0530 (8) | 0.0158 (7) | 0.0042 (7) | 0.0011 (7) |
C4 | 0.0427 (6) | 0.0529 (8) | 0.0463 (7) | 0.0164 (6) | 0.0079 (5) | 0.0086 (6) |
C5 | 0.0602 (9) | 0.0751 (11) | 0.0613 (9) | 0.0189 (8) | 0.0116 (7) | 0.0257 (8) |
C6 | 0.0914 (14) | 0.125 (2) | 0.0543 (10) | 0.0340 (14) | 0.0154 (10) | 0.0323 (12) |
C7 | 0.135 (2) | 0.124 (2) | 0.0474 (10) | 0.0387 (18) | 0.0052 (12) | −0.0045 (12) |
C8 | 0.126 (2) | 0.0763 (13) | 0.0622 (11) | 0.0247 (13) | −0.0018 (12) | −0.0128 (10) |
C9 | 0.0411 (6) | 0.0407 (6) | 0.0489 (7) | 0.0153 (5) | 0.0091 (5) | 0.0052 (5) |
C10 | 0.0521 (8) | 0.0566 (9) | 0.0760 (10) | 0.0221 (7) | 0.0195 (7) | 0.0271 (8) |
C11 | 0.0643 (10) | 0.0824 (12) | 0.0777 (11) | 0.0404 (9) | 0.0148 (8) | 0.0316 (10) |
C12 | 0.0450 (8) | 0.0816 (12) | 0.0772 (11) | 0.0286 (8) | 0.0134 (7) | 0.0108 (9) |
C13 | 0.0506 (8) | 0.0762 (11) | 0.0874 (13) | 0.0206 (8) | 0.0307 (8) | 0.0260 (10) |
C14 | 0.0575 (8) | 0.0640 (9) | 0.0662 (9) | 0.0255 (7) | 0.0231 (7) | 0.0261 (8) |
C15 | 0.0530 (8) | 0.0702 (10) | 0.0513 (8) | 0.0207 (7) | 0.0167 (6) | 0.0205 (7) |
C16 | 0.0545 (7) | 0.0562 (8) | 0.0395 (6) | 0.0218 (6) | 0.0143 (6) | 0.0173 (6) |
C17 | 0.0616 (8) | 0.0437 (7) | 0.0499 (7) | 0.0166 (6) | 0.0080 (6) | 0.0101 (6) |
C18 | 0.0655 (9) | 0.0476 (7) | 0.0538 (8) | 0.0277 (7) | 0.0092 (7) | 0.0102 (6) |
C19 | 0.0566 (8) | 0.0526 (8) | 0.0424 (7) | 0.0226 (6) | 0.0066 (6) | 0.0126 (6) |
C20 | 0.0703 (10) | 0.0580 (9) | 0.0466 (7) | 0.0276 (8) | −0.0002 (7) | −0.0024 (6) |
C21 | 0.0705 (10) | 0.0664 (10) | 0.0467 (7) | 0.0372 (8) | 0.0092 (7) | 0.0012 (7) |
C22 | 0.0695 (12) | 0.0920 (15) | 0.0846 (13) | 0.0189 (11) | −0.0098 (10) | −0.0116 (11) |
C23 | 0.130 (2) | 0.0469 (10) | 0.1088 (18) | −0.0001 (11) | −0.0013 (15) | 0.0169 (11) |
S1—O2 | 1.4139 (13) | C11—C12 | 1.370 (3) |
S1—O1 | 1.4208 (13) | C11—H11 | 0.9300 |
S1—N1 | 1.6607 (11) | C12—C13 | 1.370 (3) |
S1—C9 | 1.7534 (13) | C12—H12 | 0.9300 |
N1—C4 | 1.4202 (17) | C13—C14 | 1.370 (2) |
N1—C1 | 1.4376 (17) | C13—H13 | 0.9300 |
O3—C19 | 1.3664 (18) | C14—H14 | 0.9300 |
O3—C22 | 1.411 (2) | C15—C16 | 1.518 (2) |
C1—C2 | 1.343 (2) | C15—H15A | 0.9700 |
C1—C15 | 1.497 (2) | C15—H15B | 0.9700 |
C2—C3 | 1.435 (2) | C16—C21 | 1.378 (2) |
C2—C23 | 1.502 (2) | C16—C17 | 1.386 (2) |
C3—C4 | 1.388 (2) | C17—C18 | 1.378 (2) |
C3—C8 | 1.392 (2) | C17—H17 | 0.9300 |
C4—C5 | 1.382 (2) | C18—C19 | 1.384 (2) |
C5—C6 | 1.382 (3) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.378 (2) |
C6—C7 | 1.375 (4) | C20—C21 | 1.389 (2) |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C8 | 1.366 (3) | C21—H21 | 0.9300 |
C7—H7 | 0.9300 | C22—H22A | 0.9600 |
C8—H8 | 0.9300 | C22—H22B | 0.9600 |
C9—C10 | 1.376 (2) | C22—H22C | 0.9600 |
C9—C14 | 1.378 (2) | C23—H23A | 0.9600 |
C10—C11 | 1.381 (2) | C23—H23B | 0.9600 |
C10—H10 | 0.9300 | C23—H23C | 0.9600 |
O2—S1—O1 | 119.46 (8) | C11—C12—H12 | 119.9 |
O2—S1—N1 | 107.52 (7) | C13—C12—H12 | 119.9 |
O1—S1—N1 | 106.30 (7) | C14—C13—C12 | 120.39 (15) |
O2—S1—C9 | 109.12 (7) | C14—C13—H13 | 119.8 |
O1—S1—C9 | 108.34 (7) | C12—C13—H13 | 119.8 |
N1—S1—C9 | 105.19 (6) | C13—C14—C9 | 119.12 (14) |
C4—N1—C1 | 107.26 (11) | C13—C14—H14 | 120.4 |
C4—N1—S1 | 119.34 (9) | C9—C14—H14 | 120.4 |
C1—N1—S1 | 124.73 (9) | C1—C15—C16 | 113.44 (12) |
C19—O3—C22 | 118.68 (14) | C1—C15—H15A | 108.9 |
C2—C1—N1 | 108.44 (12) | C16—C15—H15A | 108.9 |
C2—C1—C15 | 127.66 (14) | C1—C15—H15B | 108.9 |
N1—C1—C15 | 123.39 (13) | C16—C15—H15B | 108.9 |
C1—C2—C3 | 108.85 (14) | H15A—C15—H15B | 107.7 |
C1—C2—C23 | 127.78 (17) | C21—C16—C17 | 117.55 (14) |
C3—C2—C23 | 123.32 (17) | C21—C16—C15 | 122.13 (13) |
C4—C3—C8 | 119.54 (17) | C17—C16—C15 | 120.31 (14) |
C4—C3—C2 | 108.13 (14) | C18—C17—C16 | 121.48 (14) |
C8—C3—C2 | 132.33 (18) | C18—C17—H17 | 119.3 |
C5—C4—C3 | 122.00 (15) | C16—C17—H17 | 119.3 |
C5—C4—N1 | 130.70 (15) | C17—C18—C19 | 120.15 (13) |
C3—C4—N1 | 107.29 (12) | C17—C18—H18 | 119.9 |
C4—C5—C6 | 117.04 (19) | C19—C18—H18 | 119.9 |
C4—C5—H5 | 121.5 | O3—C19—C20 | 125.29 (14) |
C6—C5—H5 | 121.5 | O3—C19—C18 | 115.38 (13) |
C7—C6—C5 | 121.58 (19) | C20—C19—C18 | 119.33 (14) |
C7—C6—H6 | 119.2 | C19—C20—C21 | 119.66 (14) |
C5—C6—H6 | 119.2 | C19—C20—H20 | 120.2 |
C8—C7—C6 | 121.2 (2) | C21—C20—H20 | 120.2 |
C8—C7—H7 | 119.4 | C16—C21—C20 | 121.81 (14) |
C6—C7—H7 | 119.4 | C16—C21—H21 | 119.1 |
C7—C8—C3 | 118.6 (2) | C20—C21—H21 | 119.1 |
C7—C8—H8 | 120.7 | O3—C22—H22A | 109.5 |
C3—C8—H8 | 120.7 | O3—C22—H22B | 109.5 |
C10—C9—C14 | 121.16 (13) | H22A—C22—H22B | 109.5 |
C10—C9—S1 | 119.39 (11) | O3—C22—H22C | 109.5 |
C14—C9—S1 | 119.44 (11) | H22A—C22—H22C | 109.5 |
C9—C10—C11 | 118.78 (15) | H22B—C22—H22C | 109.5 |
C9—C10—H10 | 120.6 | C2—C23—H23A | 109.5 |
C11—C10—H10 | 120.6 | C2—C23—H23B | 109.5 |
C12—C11—C10 | 120.27 (15) | H23A—C23—H23B | 109.5 |
C12—C11—H11 | 119.9 | C2—C23—H23C | 109.5 |
C10—C11—H11 | 119.9 | H23A—C23—H23C | 109.5 |
C11—C12—C13 | 120.28 (15) | H23B—C23—H23C | 109.5 |
O2—S1—N1—C4 | 178.01 (11) | C2—C3—C8—C7 | −179.2 (2) |
O1—S1—N1—C4 | −52.97 (12) | O2—S1—C9—C10 | 132.11 (13) |
C9—S1—N1—C4 | 61.81 (11) | O1—S1—C9—C10 | 0.56 (15) |
O2—S1—N1—C1 | 34.54 (13) | N1—S1—C9—C10 | −112.79 (13) |
O1—S1—N1—C1 | 163.56 (11) | O2—S1—C9—C14 | −46.57 (14) |
C9—S1—N1—C1 | −81.67 (11) | O1—S1—C9—C14 | −178.11 (12) |
C4—N1—C1—C2 | 2.16 (15) | N1—S1—C9—C14 | 68.54 (13) |
S1—N1—C1—C2 | 149.25 (12) | C14—C9—C10—C11 | 0.2 (2) |
C4—N1—C1—C15 | 174.49 (12) | S1—C9—C10—C11 | −178.41 (13) |
S1—N1—C1—C15 | −38.42 (17) | C9—C10—C11—C12 | −1.0 (3) |
N1—C1—C2—C3 | −1.54 (18) | C10—C11—C12—C13 | 1.1 (3) |
C15—C1—C2—C3 | −173.45 (14) | C11—C12—C13—C14 | −0.4 (3) |
N1—C1—C2—C23 | 175.7 (2) | C12—C13—C14—C9 | −0.3 (3) |
C15—C1—C2—C23 | 3.8 (3) | C10—C9—C14—C13 | 0.4 (2) |
C1—C2—C3—C4 | 0.3 (2) | S1—C9—C14—C13 | 179.05 (13) |
C23—C2—C3—C4 | −177.07 (19) | C2—C1—C15—C16 | 99.95 (19) |
C1—C2—C3—C8 | 179.5 (2) | N1—C1—C15—C16 | −70.85 (18) |
C23—C2—C3—C8 | 2.1 (3) | C1—C15—C16—C21 | 114.27 (16) |
C8—C3—C4—C5 | 0.4 (3) | C1—C15—C16—C17 | −66.92 (18) |
C2—C3—C4—C5 | 179.70 (15) | C21—C16—C17—C18 | −1.3 (2) |
C8—C3—C4—N1 | −178.30 (17) | C15—C16—C17—C18 | 179.83 (13) |
C2—C3—C4—N1 | 1.01 (17) | C16—C17—C18—C19 | 0.0 (2) |
C1—N1—C4—C5 | 179.56 (15) | C22—O3—C19—C20 | −1.0 (2) |
S1—N1—C4—C5 | 30.4 (2) | C22—O3—C19—C18 | 178.76 (17) |
C1—N1—C4—C3 | −1.91 (15) | C17—C18—C19—O3 | −178.49 (13) |
S1—N1—C4—C3 | −151.10 (11) | C17—C18—C19—C20 | 1.3 (2) |
C3—C4—C5—C6 | −0.5 (2) | O3—C19—C20—C21 | 178.59 (14) |
N1—C4—C5—C6 | 177.85 (16) | C18—C19—C20—C21 | −1.1 (2) |
C4—C5—C6—C7 | 0.3 (3) | C17—C16—C21—C20 | 1.4 (2) |
C5—C6—C7—C8 | 0.0 (4) | C15—C16—C21—C20 | −179.72 (14) |
C6—C7—C8—C3 | −0.1 (4) | C19—C20—C21—C16 | −0.2 (2) |
C4—C3—C8—C7 | −0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.93 | 2.39 | 2.970 (2) | 120 |
C15—H15B···O2 | 0.97 | 2.28 | 2.883 (2) | 119 |
C21—H21···O2 | 0.93 | 2.56 | 3.127 (2) | 120 |
C13—H13···Cgi | 0.93 | 2.77 | 3.527 (2) | 139 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C23H21NO3S |
Mr | 391.47 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.2518 (3), 10.0817 (4), 12.8169 (5) |
α, β, γ (°) | 97.244 (2), 97.876 (2), 105.709 (2) |
V (Å3) | 1001.76 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.24 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23750, 5432, 4234 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.687 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.126, 1.04 |
No. of reflections | 5432 |
No. of parameters | 254 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.26 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.93 | 2.39 | 2.970 (2) | 120 |
C15—H15B···O2 | 0.97 | 2.28 | 2.883 (2) | 119 |
C21—H21···O2 | 0.93 | 2.56 | 3.127 (2) | 120 |
C13—H13···Cgi | 0.93 | 2.77 | 3.527 (2) | 139 |
Symmetry code: (i) x+1, y, z. |
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Indole compounds are used as bioactive drugs (Stevenson et al., 2000). The indole derivatives exhibit antituberculosis (Karali et al., 2007), anti-HIV (Ragno et al., 2006), central nervous system depressant and muscle relaxant properties (Harris & Uhle, 1960; Ho et al., 1986). Herein, we report the crystal structure of the title compound, (I).
In the molecule, the planar sulfonyl bound phenyl group subtends an angle of 77.7 (1)° with the planar indole moiety. The methyl atom is deviated from the indole ring by 0.075 (3) Å. The bond lengths and bond angles in the molecule are comparable with the values reported in literature (Palani et al., 2006a,b). The methoxy group also lies in the plane of the benzyl ring. The methoxybenzyl group is oriented at angle of 80.1 (1)° with respect to the indole moiety. The geometry around S1 is distorted from tetrahedral values. The widening of the angle (O1—S1—O2=) 119.46 (8)° and narrowing of the angle (N1—S1—C9=) 105.19 (6)° are due to the electon withdrawing character of the phenyl sulfonyl group. The sum of the bond angle around N1 indicates that the atom is in an sp2 hybridized state.
A few C—H···O intramolecular interactions play the role to stabilize the molecules in addition to a C—H···π interaction (Table 1). The molecules in the unit cell are packed by van der Waals forces.