In the title compound, C
19H
17NO
5S, the indole system is not strictly planar and the dihedral angle between the fused rings is 2.1 (1)°. The indole and phenyl rings are orthogonal to each other and the dihedral angle between them is 87.2 (1)°. The molecules are joined into head-to-head dimers by hydrogen bonds involving the butyric acid groups. The centrosymmetrically related C—H
O hydrogen bond pattern joins the head-to-head dimers into chains running parallel to the
c axis. Neighbouring chains are held together by weak C—H
π and π–π interactions.
Supporting information
CCDC reference: 214854
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.149
- Data-to-parameter ratio = 17.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
The title compound was prepared by the Friedel–Crafts acylation of 1-phenylsulfonly-2-methylindole with succinic anhydride in the presence of anhydrous aluminium chloride in dry methylene chloride.
All H atoms were included in calculated positions and allowed to ride on their corresponding parent atoms.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
3-(1-Phenylsulfonyl-2-methylindol-3-ylcarbonyl)propanoic acid
top
Crystal data top
C19H17NO5S | Z = 2 |
Mr = 371.40 | F(000) = 388 |
Triclinic, P1 | Dx = 1.423 Mg m−3 |
a = 8.1825 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.9758 (1) Å | Cell parameters from 3857 reflections |
c = 12.3121 (1) Å | θ = 1.8–28.3° |
α = 69.281 (1)° | µ = 0.22 mm−1 |
β = 72.067 (1)° | T = 293 K |
γ = 70.878 (1)° | Block, colourless |
V = 866.92 (2) Å3 | 0.46 × 0.42 × 0.24 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 3144 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 28.3°, θmin = 1.8° |
ω scans | h = −10→8 |
6104 measured reflections | k = −13→12 |
4175 independent reflections | l = −16→13 |
Refinement top
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.091P)2] where P = (Fo2 + 2Fc2)/3 |
4175 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
Crystal data top
C19H17NO5S | γ = 70.878 (1)° |
Mr = 371.40 | V = 866.92 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1825 (2) Å | Mo Kα radiation |
b = 9.9758 (1) Å | µ = 0.22 mm−1 |
c = 12.3121 (1) Å | T = 293 K |
α = 69.281 (1)° | 0.46 × 0.42 × 0.24 mm |
β = 72.067 (1)° | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 3144 reflections with I > 2σ(I) |
6104 measured reflections | Rint = 0.025 |
4175 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.54 e Å−3 |
4175 reflections | Δρmin = −0.48 e Å−3 |
236 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.50958 (6) | 0.07847 (6) | 0.31671 (4) | 0.04313 (17) | |
O1 | 0.5320 (2) | −0.07044 (18) | 0.38969 (12) | 0.0594 (4) | |
O2 | 0.34092 (18) | 0.1803 (2) | 0.33014 (14) | 0.0592 (4) | |
O3 | 0.5942 (3) | 0.38243 (17) | −0.16717 (15) | 0.0787 (6) | |
O4 | 0.9696 (2) | 0.34093 (18) | −0.41035 (15) | 0.0667 (5) | |
O5 | 0.7594 (2) | 0.52339 (17) | −0.48807 (15) | 0.0655 (5) | |
H5 | 0.8387 | 0.5671 | −0.5141 | 0.098* | |
N1 | 0.5662 (2) | 0.06819 (18) | 0.17460 (13) | 0.0405 (4) | |
C2 | 0.5299 (2) | 0.1871 (2) | 0.07346 (16) | 0.0402 (4) | |
C3 | 0.6399 (2) | 0.1493 (2) | −0.02604 (15) | 0.0389 (4) | |
C4 | 0.7505 (2) | 0.0013 (2) | 0.01113 (16) | 0.0379 (4) | |
C5 | 0.7065 (2) | −0.0455 (2) | 0.13608 (16) | 0.0390 (4) | |
C6 | 0.7942 (3) | −0.1812 (2) | 0.20103 (19) | 0.0515 (5) | |
H6 | 0.7638 | −0.2105 | 0.2837 | 0.062* | |
C7 | 0.9275 (3) | −0.2708 (2) | 0.1393 (2) | 0.0549 (5) | |
H7 | 0.9889 | −0.3613 | 0.1810 | 0.066* | |
C8 | 0.9716 (3) | −0.2284 (2) | 0.0158 (2) | 0.0550 (5) | |
H8 | 1.0607 | −0.2915 | −0.0239 | 0.066* | |
C9 | 0.8852 (3) | −0.0940 (2) | −0.04857 (19) | 0.0497 (5) | |
H9 | 0.9160 | −0.0665 | −0.1313 | 0.060* | |
C10 | 0.6703 (2) | 0.1553 (2) | 0.32291 (15) | 0.0354 (4) | |
C11 | 0.8229 (3) | 0.0634 (2) | 0.36120 (17) | 0.0429 (4) | |
H11 | 0.8393 | −0.0387 | 0.3870 | 0.051* | |
C12 | 0.9508 (2) | 0.1286 (3) | 0.35991 (19) | 0.0490 (5) | |
H12 | 1.0545 | 0.0693 | 0.3847 | 0.059* | |
C13 | 0.9246 (3) | 0.2797 (2) | 0.32226 (19) | 0.0499 (5) | |
H13 | 1.0116 | 0.3218 | 0.3208 | 0.060* | |
C14 | 0.7714 (3) | 0.3693 (2) | 0.2868 (2) | 0.0553 (5) | |
H14 | 0.7544 | 0.4714 | 0.2625 | 0.066* | |
C15 | 0.6419 (3) | 0.3071 (2) | 0.2873 (2) | 0.0481 (5) | |
H15 | 0.5375 | 0.3670 | 0.2640 | 0.058* | |
C16 | 0.3821 (3) | 0.3227 (3) | 0.0792 (2) | 0.0580 (6) | |
H16A | 0.4190 | 0.3896 | 0.1013 | 0.087* | |
H16B | 0.2805 | 0.2955 | 0.1374 | 0.087* | |
H16C | 0.3521 | 0.3700 | 0.0028 | 0.087* | |
C17 | 0.6432 (3) | 0.2493 (2) | −0.14853 (17) | 0.0438 (4) | |
C18 | 0.7129 (3) | 0.1844 (2) | −0.25187 (16) | 0.0450 (4) | |
H18A | 0.6551 | 0.1068 | −0.2368 | 0.054* | |
H18B | 0.8389 | 0.1397 | −0.2581 | 0.054* | |
C19 | 0.6834 (3) | 0.2986 (2) | −0.36994 (17) | 0.0485 (5) | |
H19A | 0.6893 | 0.2480 | −0.4259 | 0.058* | |
H19B | 0.5657 | 0.3635 | −0.3574 | 0.058* | |
C20 | 0.8174 (3) | 0.3898 (2) | −0.42252 (16) | 0.0453 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0373 (3) | 0.0634 (3) | 0.0339 (2) | −0.0278 (2) | 0.00063 (18) | −0.0130 (2) |
O1 | 0.0784 (11) | 0.0707 (10) | 0.0356 (7) | −0.0471 (9) | −0.0023 (7) | −0.0048 (7) |
O2 | 0.0301 (7) | 0.0998 (12) | 0.0534 (9) | −0.0213 (7) | 0.0010 (6) | −0.0317 (9) |
O3 | 0.1296 (18) | 0.0431 (9) | 0.0502 (9) | −0.0043 (10) | −0.0254 (10) | −0.0082 (7) |
O4 | 0.0577 (10) | 0.0624 (10) | 0.0679 (10) | −0.0298 (8) | −0.0220 (8) | 0.0167 (8) |
O5 | 0.0639 (10) | 0.0526 (9) | 0.0722 (11) | −0.0240 (8) | −0.0239 (8) | 0.0080 (8) |
N1 | 0.0403 (8) | 0.0504 (9) | 0.0327 (7) | −0.0188 (7) | −0.0043 (6) | −0.0099 (7) |
C2 | 0.0381 (9) | 0.0477 (10) | 0.0391 (9) | −0.0165 (8) | −0.0090 (7) | −0.0112 (8) |
C3 | 0.0432 (10) | 0.0429 (10) | 0.0341 (9) | −0.0177 (8) | −0.0082 (7) | −0.0085 (7) |
C4 | 0.0410 (9) | 0.0407 (9) | 0.0359 (9) | −0.0187 (8) | −0.0079 (7) | −0.0078 (7) |
C5 | 0.0407 (10) | 0.0438 (10) | 0.0371 (9) | −0.0217 (8) | −0.0078 (7) | −0.0071 (7) |
C6 | 0.0611 (13) | 0.0501 (11) | 0.0420 (10) | −0.0216 (10) | −0.0144 (9) | −0.0013 (9) |
C7 | 0.0590 (13) | 0.0404 (10) | 0.0622 (13) | −0.0115 (10) | −0.0226 (11) | −0.0036 (9) |
C8 | 0.0558 (13) | 0.0473 (12) | 0.0588 (13) | −0.0093 (10) | −0.0094 (10) | −0.0171 (10) |
C9 | 0.0561 (12) | 0.0469 (11) | 0.0430 (10) | −0.0157 (9) | −0.0028 (9) | −0.0131 (9) |
C10 | 0.0293 (8) | 0.0460 (10) | 0.0314 (8) | −0.0141 (7) | −0.0017 (6) | −0.0111 (7) |
C11 | 0.0379 (9) | 0.0437 (10) | 0.0444 (10) | −0.0073 (8) | −0.0100 (8) | −0.0109 (8) |
C12 | 0.0302 (9) | 0.0676 (14) | 0.0510 (11) | −0.0071 (9) | −0.0103 (8) | −0.0220 (10) |
C13 | 0.0354 (10) | 0.0660 (13) | 0.0576 (12) | −0.0212 (9) | −0.0037 (9) | −0.0257 (11) |
C14 | 0.0534 (13) | 0.0479 (11) | 0.0699 (14) | −0.0197 (10) | −0.0155 (11) | −0.0143 (10) |
C15 | 0.0405 (10) | 0.0463 (11) | 0.0587 (12) | −0.0095 (8) | −0.0191 (9) | −0.0100 (9) |
C16 | 0.0540 (13) | 0.0633 (14) | 0.0521 (12) | −0.0041 (11) | −0.0121 (10) | −0.0196 (11) |
C17 | 0.0499 (11) | 0.0420 (10) | 0.0391 (10) | −0.0142 (9) | −0.0111 (8) | −0.0069 (8) |
C18 | 0.0560 (12) | 0.0459 (10) | 0.0350 (9) | −0.0259 (9) | −0.0043 (8) | −0.0063 (8) |
C19 | 0.0554 (12) | 0.0596 (12) | 0.0349 (9) | −0.0288 (10) | −0.0079 (8) | −0.0067 (9) |
C20 | 0.0535 (12) | 0.0495 (11) | 0.0322 (9) | −0.0223 (9) | −0.0095 (8) | −0.0019 (8) |
Geometric parameters (Å, º) top
S1—O2 | 1.422 (2) | C9—H9 | 0.9300 |
S1—O1 | 1.424 (2) | C10—C15 | 1.379 (3) |
S1—N1 | 1.698 (2) | C10—C11 | 1.389 (3) |
S1—C10 | 1.757 (2) | C11—C12 | 1.395 (3) |
O3—C17 | 1.212 (2) | C11—H11 | 0.9300 |
O4—C20 | 1.215 (3) | C12—C13 | 1.375 (3) |
O5—C20 | 1.309 (2) | C12—H12 | 0.9300 |
O5—H5 | 0.8200 | C13—C14 | 1.374 (3) |
N1—C2 | 1.414 (2) | C13—H13 | 0.9300 |
N1—C5 | 1.422 (2) | C14—C15 | 1.390 (3) |
C2—C3 | 1.371 (3) | C14—H14 | 0.9300 |
C2—C16 | 1.497 (3) | C15—H15 | 0.9300 |
C3—C4 | 1.453 (3) | C16—H16A | 0.9600 |
C3—C17 | 1.483 (2) | C16—H16B | 0.9600 |
C4—C9 | 1.402 (3) | C16—H16C | 0.9600 |
C4—C5 | 1.405 (2) | C17—C18 | 1.502 (3) |
C5—C6 | 1.392 (3) | C18—C19 | 1.527 (3) |
C6—C7 | 1.377 (3) | C18—H18A | 0.9700 |
C6—H6 | 0.9300 | C18—H18B | 0.9700 |
C7—C8 | 1.388 (3) | C19—C20 | 1.499 (3) |
C7—H7 | 0.9300 | C19—H19A | 0.9700 |
C8—C9 | 1.378 (3) | C19—H19B | 0.9700 |
C8—H8 | 0.9300 | | |
| | | |
O2—S1—O1 | 120.1 (1) | C10—C11—H11 | 120.9 |
O2—S1—N1 | 106.9 (1) | C12—C11—H11 | 120.9 |
O1—S1—N1 | 105.6 (1) | C13—C12—C11 | 120.4 (2) |
O2—S1—C10 | 109.3 (1) | C13—C12—H12 | 119.8 |
O1—S1—C10 | 109.9 (1) | C11—C12—H12 | 119.8 |
N1—S1—C10 | 103.7 (1) | C14—C13—C12 | 120.7 (2) |
C20—O5—H5 | 109.5 | C14—C13—H13 | 119.7 |
C2—N1—C5 | 108.5 (1) | C12—C13—H13 | 119.7 |
C2—N1—S1 | 125.8 (1) | C13—C14—C15 | 120.0 (2) |
C5—N1—S1 | 122.6 (1) | C13—C14—H14 | 120.0 |
C3—C2—N1 | 108.5 (2) | C15—C14—H14 | 120.0 |
C3—C2—C16 | 127.8 (2) | C10—C15—C14 | 119.1 (2) |
N1—C2—C16 | 123.4 (2) | C10—C15—H15 | 120.4 |
C2—C3—C4 | 108.4 (2) | C14—C15—H15 | 120.4 |
C2—C3—C17 | 123.7 (2) | C2—C16—H16A | 109.5 |
C4—C3—C17 | 127.9 (2) | C2—C16—H16B | 109.5 |
C9—C4—C5 | 118.3 (2) | H16A—C16—H16B | 109.5 |
C9—C4—C3 | 134.6 (2) | C2—C16—H16C | 109.5 |
C5—C4—C3 | 107.1 (2) | H16A—C16—H16C | 109.5 |
C6—C5—C4 | 122.0 (2) | H16B—C16—H16C | 109.5 |
C6—C5—N1 | 130.6 (2) | O3—C17—C3 | 121.4 (2) |
C4—C5—N1 | 107.4 (2) | O3—C17—C18 | 119.3 (2) |
C7—C6—C5 | 118.1 (2) | C3—C17—C18 | 119.3 (2) |
C7—C6—H6 | 121.0 | C17—C18—C19 | 113.0 (2) |
C5—C6—H6 | 121.0 | C17—C18—H18A | 109.0 |
C6—C7—C8 | 121.1 (2) | C19—C18—H18A | 109.0 |
C6—C7—H7 | 119.4 | C17—C18—H18B | 109.0 |
C8—C7—H7 | 119.4 | C19—C18—H18B | 109.0 |
C9—C8—C7 | 120.9 (2) | H18A—C18—H18B | 107.8 |
C9—C8—H8 | 119.6 | C20—C19—C18 | 112.6 (2) |
C7—C8—H8 | 119.6 | C20—C19—H19A | 109.1 |
C8—C9—C4 | 119.7 (2) | C18—C19—H19A | 109.1 |
C8—C9—H9 | 120.1 | C20—C19—H19B | 109.1 |
C4—C9—H9 | 120.1 | C18—C19—H19B | 109.1 |
C15—C10—C11 | 121.6 (2) | H19A—C19—H19B | 107.8 |
C15—C10—S1 | 118.5 (1) | O4—C20—O5 | 122.9 (2) |
C11—C10—S1 | 119.9 (1) | O4—C20—C19 | 122.7 (2) |
C10—C11—C12 | 118.2 (2) | O5—C20—C19 | 114.4 (2) |
| | | |
O2—S1—N1—C2 | 36.8 (2) | C5—C6—C7—C8 | −0.9 (3) |
O1—S1—N1—C2 | 165.8 (2) | C6—C7—C8—C9 | 1.1 (4) |
C10—S1—N1—C2 | −78.7 (2) | C7—C8—C9—C4 | −0.2 (3) |
O2—S1—N1—C5 | −165.8 (1) | C5—C4—C9—C8 | −0.9 (3) |
O1—S1—N1—C5 | −36.8 (2) | C3—C4—C9—C8 | 176.7 (2) |
C10—S1—N1—C5 | 78.8 (2) | O2—S1—C10—C15 | −27.9 (2) |
C5—N1—C2—C3 | 1.3 (2) | O1—S1—C10—C15 | −161.7 (2) |
S1—N1—C2—C3 | 161.4 (1) | N1—S1—C10—C15 | 85.8 (2) |
C5—N1—C2—C16 | 176.0 (2) | O2—S1—C10—C11 | 153.2 (2) |
S1—N1—C2—C16 | −23.9 (3) | O1—S1—C10—C11 | 19.3 (2) |
N1—C2—C3—C4 | 0.3 (2) | N1—S1—C10—C11 | −93.2 (2) |
C16—C2—C3—C4 | −174.1 (2) | C15—C10—C11—C12 | −1.7 (3) |
N1—C2—C3—C17 | −178.0 (2) | S1—C10—C11—C12 | 177.2 (1) |
C16—C2—C3—C17 | 7.6 (3) | C10—C11—C12—C13 | 0.4 (3) |
C2—C3—C4—C9 | −179.7 (2) | C11—C12—C13—C14 | 0.9 (3) |
C17—C3—C4—C9 | −1.5 (3) | C12—C13—C14—C15 | −0.8 (3) |
C2—C3—C4—C5 | −1.9 (2) | C11—C10—C15—C14 | 1.7 (3) |
C17—C3—C4—C5 | 176.4 (2) | S1—C10—C15—C14 | −177.2 (2) |
C9—C4—C5—C6 | 1.1 (3) | C13—C14—C15—C10 | −0.5 (3) |
C3—C4—C5—C6 | −177.1 (2) | C2—C3—C17—O3 | 24.3 (3) |
C9—C4—C5—N1 | −179.1 (2) | C4—C3—C17—O3 | −153.7 (2) |
C3—C4—C5—N1 | 2.7 (2) | C2—C3—C17—C18 | −157.3 (2) |
C2—N1—C5—C6 | 177.3 (2) | C4—C3—C17—C18 | 24.7 (3) |
S1—N1—C5—C6 | 16.4 (3) | O3—C17—C18—C19 | −9.8 (3) |
C2—N1—C5—C4 | −2.5 (2) | C3—C17—C18—C19 | 171.8 (2) |
S1—N1—C5—C4 | −163.4 (1) | C17—C18—C19—C20 | 79.6 (2) |
C4—C5—C6—C7 | −0.2 (3) | C18—C19—C20—O4 | 32.9 (3) |
N1—C5—C6—C7 | −179.9 (2) | C18—C19—C20—O5 | −150.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.93 | 2.30 | 2.901 (3) | 122 |
C16—H16B···O2 | 0.96 | 2.37 | 2.871 (3) | 112 |
C16—H16C···O3 | 0.96 | 2.40 | 2.954 (3) | 117 |
C18—H18B···O4 | 0.97 | 2.49 | 2.851 (3) | 102 |
O5—H5···O4i | 0.82 | 1.90 | 2.715 (2) | 173 |
C15—H15···O3ii | 0.93 | 2.40 | 3.180 (3) | 142 |
C8—H8···Cgiii | 0.93 | 3.39 | 3.997 (2) | 125 |
C9—H9···Cgiii | 0.93 | 3.19 | 3.893 (2) | 134 |
C19—H19A···Cgiv | 0.97 | 3.04 | 3.910 (3) | 150 |
Symmetry codes: (i) −x+2, −y+1, −z−1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y, −z; (iv) x, y, z−1. |
Experimental details
Crystal data |
Chemical formula | C19H17NO5S |
Mr | 371.40 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.1825 (2), 9.9758 (1), 12.3121 (1) |
α, β, γ (°) | 69.281 (1), 72.067 (1), 70.878 (1) |
V (Å3) | 866.92 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.46 × 0.42 × 0.24 |
|
Data collection |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6104, 4175, 3144 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.666 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.149, 1.03 |
No. of reflections | 4175 |
No. of parameters | 236 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.54, −0.48 |
Selected geometric parameters (Å, º) topS1—O2 | 1.422 (2) | O4—C20 | 1.215 (3) |
S1—O1 | 1.424 (2) | O5—C20 | 1.309 (2) |
S1—N1 | 1.698 (2) | N1—C2 | 1.414 (2) |
S1—C10 | 1.757 (2) | N1—C5 | 1.422 (2) |
O3—C17 | 1.212 (2) | | |
| | | |
O2—S1—O1 | 120.1 (1) | N1—S1—C10 | 103.7 (1) |
O2—S1—N1 | 106.9 (1) | C2—N1—C5 | 108.5 (1) |
O1—S1—N1 | 105.6 (1) | C2—N1—S1 | 125.8 (1) |
O2—S1—C10 | 109.3 (1) | C5—N1—S1 | 122.6 (1) |
O1—S1—C10 | 109.9 (1) | | |
| | | |
C10—S1—N1—C2 | −78.7 (2) | S1—N1—C2—C16 | −23.9 (3) |
C10—S1—N1—C5 | 78.8 (2) | S1—N1—C5—C6 | 16.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.93 | 2.30 | 2.901 (3) | 122 |
C16—H16B···O2 | 0.96 | 2.37 | 2.871 (3) | 112 |
C16—H16C···O3 | 0.96 | 2.40 | 2.954 (3) | 117 |
C18—H18B···O4 | 0.97 | 2.49 | 2.851 (3) | 102 |
O5—H5···O4i | 0.82 | 1.90 | 2.715 (2) | 173 |
C15—H15···O3ii | 0.93 | 2.40 | 3.180 (3) | 142 |
C8—H8···Cgiii | 0.93 | 3.39 | 3.997 (2) | 125 |
C9—H9···Cgiii | 0.93 | 3.19 | 3.893 (2) | 134 |
C19—H19A···Cgiv | 0.97 | 3.04 | 3.910 (3) | 150 |
Symmetry codes: (i) −x+2, −y+1, −z−1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y, −z; (iv) x, y, z−1. |
Indole is an important heterocyclic compounds. Its ring system is present in a large number of natural products. Many of these natural products, as well as the synthetic derivatives, show a variety of useful biological properties, such as antibacterial (Okabe & Adachi, 1998), antitumour (Schollmeyer et al., 1995), antidepressant (Grinev et al., 1984), antimicrobial (El-Sayed et al., 1986; Gadaginamath & Patil, 1999) and anti-inflammatory (Rodriguez et al., 1985) activities. 4-(3-Indolyl)butyric acid (IBA) is known to possess growth-regulating activity (Steward & Krikorian, 1971). IBA shows a root-promoting effect in all lemon and lime varieties (Sircar, 1971) and is also effective in bud inhibition in many plants. The interaction of phenylsulfonylindole with the calf-thymus DNA by spectroscopic methods has also been studied (Sivaraman et al., 1996). Indoles have been proved to display high aldose reductose inhibitory activity (Rajeswaran et al., 1999). The structure determination of the title compound, (I), was undertaken as part of our studies on indole derivatives.
The indole system is not strictly planar and the dihedral angle formed by the pyrrole and benzene planes is 2.1 (1)°. The dihedral angle between the indole system and the phenyl ring is 87.2 (1)°. The 4-oxobutyric acid group is characterized by two planes, viz. the 3-oxopropyl group and the acid group. The plane of the indole system makes angles of 36.3 (1) and 68.2 (1)° with the 3-oxopropyl group and the acid group, respectively. Atoms S1, C16 and C17 deviate from the weighted least-squares plane through the indole system by −0.392 (1), 0.072 (3) and −0.108 (2) Å, respectively. Atoms N1 deviates by 0.155 (2) Å from the mean plane passing through atoms C2, C5 and S1. This slight pyramidalization behaviour is also observed in related indole derivatives (Sankaranarayanan et al., 2000, 2001). The bond angles around S1 show distorted tetrahedral geometry. The widening of the O1—S1—O2 angle [120.1 (1)°] from the tetrahedral value is presumably the results of repulsive interactions between the short S═O bonds. Similar observations have been noted in the related structure (Sankaranarayanan et al., 2001). The S—C bond distance [1.757 (2) Å] agrees well with the literature value of 1.758 (13) Å (Allen et al., 1987) and S—N [1.698 (2) Å] bond distance is sligtly longer than the literature value of 1.642 (24) Å (Allen et al., 1987). The lengthening of the C—N distances in the pyrrole ring is due to the electron- withdrawing character of the phenylsulfonyl group. The 3-oxopropyl chain bond lengths and angles are in the expected ranges but its conformation is of interest. The torsion angles C2—C3—C17—O3, C4—C3—C17—C18, C3—C17—C18—C19, C17—C18—C19—C20, and C18—C19—C20—O4 are 24.3 (3), 24.7 (3), 171.8 (2), 79.6 (2) and 32.9 (3)°, respectively. C—H···O interactions have been recognized as important secondary interactions and, in many cases, play a dominant role in the molecular conformation (Steiner, 1997). Four such intramolecular interactions can be identified in the present structure. The conformation of the aliphatic chain is governed by two C—H···O intramolecular interactions. Evidence for steric strain is seen at the point where the phenylsulfonyl group joins the indole. The sulfonyl group comprising of atoms O1, O2 and S1, is prevented from lying in the plane of the indole ring by close approach of O1 and H atom bound to C6, while O2 is close to the methyl substituent at C2. Thus, the orientation of the indole subtituent is influenced by weak C6—H6···O1 and C16—H16B···O2 interactions, defined by the torsion angles C6—C5—N1—S1, C5—N1—S1—C10, C16—C2—N1—S1 and C2—N1—S1—C10.
The molecules are joined into head-to-head dimers with graph-set R22(8) (Bernstein et al., 1995) by hydrogen bonds involving the carboxylic acid groups. The O5···O4 distance is 2.715 (2) Å. Centrosymmetric hydrogen bonds between atom C15 of the phenyl ring and carbonyl atom O3 of 4-oxobutyric acid form another dimer with graph-set R22(18). This hydrogen bond pattern joins the head-to-head dimers into chains running parallel to c axis. The close edge-to-face interactions are observed between A and Biii and the equivalent pair B and Aiii, with interplanar angle of 88° and centroid-centroid distance of 5.088 (2) Å [symmetry code: (iii) 2 − x, −y, −z]. Face-to-face ring interactions between P (pyrrole) ring and Pv, and ring A and Aiii, are observed which stack in the lattice along a, with centroid-centroid distances of 4.129 (2) and 3.986 (2) Å, respectively [symmetry code: (v) 1 − x, −y, −z].