Acta Cryst. (2008). E64, o732 [ doi:10.1107/S1600536808007319 ]
In the title compound, C19H18BrNO5S, the plane of the phenyl ring forms a dihedral angle of 76.99 (6)° with the indole ring system. The Br atom is disordered over two positions, with site-occupancy factors of 0.833 (14) and 0.167 (14). The molecular structure is stabilized by weak intramolecular C-H
O interactions and the crystal packing is stabilized by weak intermolecular C-HO interactions.
Ethyl 2-(methyl)-5-methoxy-1-(phenylsulfonyl)-1H-indole-3-carboxylate (1g, 2.2 mmol), N–bromo succinimide (0.4 g, 2.3 mmol), azo–bis–isobutyronitrile (50 mg) were dissolved in 50 ml of carbon tetrachloride. Refluxed on a waterbath for 2hr. Cooled to room temperature. Succinimide was filtered off over sodium sulfate. Filtrate was evaporated under reduced pressure. Product was recrystallized from methanol. Yield: 78%.
The H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, 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. The site occupancy factors for disordered Br atom is refined as Br1= 0.833 (14) and Br1A = 0.167 (14) during anisotropic refinement. The C15—Br1A distance was restrained to 1.91 (10) Å. The anisotropic displacement parameters of Br1 and Br1A were set equal by the command EADP and the anisotropic thermal parameters of C4, C5, C15 and Br1A atoms were restrained with DELU in the final cycles of refinement (Sheldrick, 2008).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./rk2082fig1thm.gif)
| Fig. 1. The molecular structure of I, with atom labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Only major fragment for disordered Br1 and C15 are drawn. Intramolecular H–bonds are shown as dashed lines. |
![[Figure 2]](./rk2082fig2thm.gif)
| Fig. 2. The packing of I, viewed down the a axis. Intermolecular H–bonds are shown as dashed lines H atoms not involving hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y+1, z]. |
| C19H18BrNO5S | Z = 2 |
| Mr = 452.31 | F000 = 460 |
| Triclinic, P1 | Dx = 1.578 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 8.9988 (3) Å | Cell parameters from 8207 reflections |
| b = 9.2343 (2) Å | θ = 2.2–27.5º |
| c = 11.6068 (3) Å | µ = 2.30 mm−1 |
| α = 82.524 (1)º | T = 295 (2) K |
| β = 87.666 (2)º | Block, colourless |
| γ = 84.942 (3)º | 0.20 × 0.20 × 0.16 mm |
| V = 952.16 (5) Å3 |
| Bruker Kappa APEXII diffractometer | 6169 independent reflections |
| Radiation source: Fine–focus sealed tube | 4163 reflections with I > 2σ(I) |
| Monochromator: Graphite | Rint = 0.027 |
| T = 295(2) K | θmax = 31.2º |
| ω and φ scans | θmin = 1.8º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
| Tmin = 0.593, Tmax = 0.692 | k = −13→13 |
| 25160 measured reflections | l = −16→16 |
| Refinement on F2 | Secondary atom site location: Difmap |
| Least-squares matrix: Full | Hydrogen site location: Geom |
| R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
| wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.054P)2 + 0.4811P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 6169 reflections | Δρmax = 0.68 e Å−3 |
| 254 parameters | Δρmin = −0.89 e Å−3 |
| 3 restraints | Extinction correction: None |
| Primary atom site location: Direct |
| C19H18BrNO5S | γ = 84.942 (3)º |
| Mr = 452.31 | V = 952.16 (5) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.9988 (3) Å | Mo Kα |
| b = 9.2343 (2) Å | µ = 2.30 mm−1 |
| c = 11.6068 (3) Å | T = 295 (2) K |
| α = 82.524 (1)º | 0.20 × 0.20 × 0.16 mm |
| β = 87.666 (2)º |
| Bruker Kappa APEXII diffractometer | 6169 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4163 reflections with I > 2σ(I) |
| Tmin = 0.593, Tmax = 0.692 | Rint = 0.027 |
| 25160 measured reflections |
| R[F2 > 2σ(F2)] = 0.044 | 3 restraints |
| wR(F2) = 0.127 | H-atom parameters constrained |
| S = 1.04 | Δρmax = 0.68 e Å−3 |
| 6169 reflections | Δρmin = −0.89 e Å−3 |
| 254 parameters |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Br1 | 0.2859 (3) | −0.0105 (2) | 0.5880 (3) | 0.0695 (4) | 0.833 (14) |
| Br1A | 0.2613 (8) | 0.0063 (7) | 0.6105 (7) | 0.0695 (4) | 0.167 (14) |
| S1 | 0.53695 (6) | 0.26331 (6) | 0.73409 (5) | 0.04656 (14) | |
| O1 | 0.6066 (2) | 0.3534 (2) | 0.80232 (18) | 0.0623 (5) | |
| O2 | 0.6249 (2) | 0.1714 (2) | 0.66452 (19) | 0.0688 (6) | |
| O3 | 0.1927 (3) | 0.2237 (2) | 1.26357 (17) | 0.0714 (6) | |
| O4 | 0.1493 (2) | −0.18350 (18) | 1.02343 (16) | 0.0551 (4) | |
| O5 | 0.2440 (3) | −0.2589 (2) | 0.8592 (2) | 0.0783 (6) | |
| N1 | 0.4384 (2) | 0.15286 (19) | 0.82973 (15) | 0.0410 (4) | |
| C1 | 0.4041 (2) | 0.3722 (2) | 0.64784 (18) | 0.0407 (4) | |
| C2 | 0.3253 (3) | 0.4881 (3) | 0.6931 (2) | 0.0499 (5) | |
| H2 | 0.3405 | 0.5062 | 0.7686 | 0.060* | |
| C3 | 0.2243 (3) | 0.5759 (3) | 0.6245 (3) | 0.0627 (7) | |
| H3 | 0.1703 | 0.6545 | 0.6537 | 0.075* | |
| C4 | 0.2020 (4) | 0.5490 (3) | 0.5135 (3) | 0.0690 (7) | |
| H4 | 0.1321 | 0.6085 | 0.4682 | 0.083* | |
| C5 | 0.2818 (4) | 0.4352 (3) | 0.4690 (2) | 0.0693 (7) | |
| H5 | 0.2663 | 0.4178 | 0.3935 | 0.083* | |
| C6 | 0.3860 (3) | 0.3453 (3) | 0.5360 (2) | 0.0561 (6) | |
| H6 | 0.4422 | 0.2688 | 0.5058 | 0.067* | |
| C7 | 0.3878 (2) | 0.0171 (2) | 0.81460 (18) | 0.0412 (4) | |
| C8 | 0.3026 (2) | −0.0297 (2) | 0.90984 (18) | 0.0393 (4) | |
| C9 | 0.2973 (2) | 0.0781 (2) | 0.98934 (17) | 0.0380 (4) | |
| C10 | 0.2300 (3) | 0.0839 (3) | 1.10015 (19) | 0.0452 (5) | |
| H10 | 0.1742 | 0.0093 | 1.1353 | 0.054* | |
| C11 | 0.2498 (3) | 0.2044 (3) | 1.1549 (2) | 0.0510 (5) | |
| C12 | 0.3333 (3) | 0.3160 (3) | 1.1024 (2) | 0.0555 (6) | |
| H12 | 0.3444 | 0.3958 | 1.1417 | 0.067* | |
| C13 | 0.3993 (3) | 0.3117 (3) | 0.9951 (2) | 0.0516 (5) | |
| H13 | 0.4547 | 0.3871 | 0.9607 | 0.062* | |
| C14 | 0.3808 (2) | 0.1902 (2) | 0.93842 (18) | 0.0399 (4) | |
| C15 | 0.4242 (3) | −0.0591 (3) | 0.7108 (2) | 0.0560 (5) | |
| H15A | 0.4287 | −0.1640 | 0.7346 | 0.067* | 0.833 (14) |
| H15B | 0.5226 | −0.0356 | 0.6808 | 0.067* | 0.833 (14) |
| H15C | 0.4302 | −0.1646 | 0.7312 | 0.067* | 0.167 (14) |
| H15D | 0.5176 | −0.0306 | 0.6736 | 0.067* | 0.167 (14) |
| C16 | 0.0958 (4) | 0.1221 (4) | 1.3175 (3) | 0.0719 (8) | |
| H16A | 0.0109 | 0.1221 | 1.2700 | 0.108* | |
| H16B | 0.0630 | 0.1487 | 1.3922 | 0.108* | |
| H16C | 0.1474 | 0.0259 | 1.3271 | 0.108* | |
| C17 | 0.2311 (3) | −0.1686 (2) | 0.9262 (2) | 0.0470 (5) | |
| C18 | 0.0781 (3) | −0.3188 (3) | 1.0520 (3) | 0.0738 (9) | |
| H18A | 0.1507 | −0.4023 | 1.0488 | 0.089* | |
| H18B | 0.0008 | −0.3243 | 0.9972 | 0.089* | |
| C19 | 0.0120 (4) | −0.3191 (5) | 1.1716 (4) | 0.1037 (15) | |
| H19A | 0.0896 | −0.3150 | 1.2252 | 0.156* | |
| H19B | −0.0375 | −0.4070 | 1.1930 | 0.156* | |
| H19C | −0.0589 | −0.2354 | 1.1739 | 0.156* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.0960 (5) | 0.0791 (4) | 0.0381 (5) | −0.0300 (4) | −0.0142 (5) | −0.0064 (4) |
| Br1A | 0.0960 (5) | 0.0791 (4) | 0.0381 (5) | −0.0300 (4) | −0.0142 (5) | −0.0064 (4) |
| S1 | 0.0417 (3) | 0.0457 (3) | 0.0503 (3) | −0.0032 (2) | 0.0003 (2) | 0.0003 (2) |
| O1 | 0.0509 (10) | 0.0655 (11) | 0.0719 (12) | −0.0198 (8) | −0.0153 (8) | 0.0002 (9) |
| O2 | 0.0616 (11) | 0.0617 (11) | 0.0763 (13) | 0.0099 (9) | 0.0226 (10) | −0.0013 (10) |
| O3 | 0.0890 (15) | 0.0806 (14) | 0.0485 (10) | −0.0023 (11) | 0.0037 (10) | −0.0285 (10) |
| O4 | 0.0634 (10) | 0.0476 (9) | 0.0544 (10) | −0.0169 (8) | −0.0054 (8) | 0.0019 (7) |
| O5 | 0.1144 (18) | 0.0565 (11) | 0.0729 (13) | −0.0309 (11) | 0.0018 (12) | −0.0271 (10) |
| N1 | 0.0493 (10) | 0.0366 (8) | 0.0368 (9) | −0.0027 (7) | −0.0047 (7) | −0.0028 (7) |
| C1 | 0.0475 (11) | 0.0364 (10) | 0.0378 (10) | −0.0087 (8) | −0.0007 (8) | 0.0004 (8) |
| C2 | 0.0592 (14) | 0.0448 (12) | 0.0446 (12) | −0.0003 (10) | −0.0010 (10) | −0.0046 (9) |
| C3 | 0.0667 (17) | 0.0526 (14) | 0.0643 (17) | 0.0067 (12) | −0.0043 (13) | 0.0026 (12) |
| C4 | 0.0731 (18) | 0.0632 (15) | 0.0666 (17) | −0.0116 (12) | −0.0220 (14) | 0.0176 (12) |
| C5 | 0.100 (2) | 0.0681 (16) | 0.0423 (13) | −0.0282 (13) | −0.0172 (13) | 0.0013 (11) |
| C6 | 0.0832 (18) | 0.0457 (12) | 0.0405 (12) | −0.0136 (12) | 0.0018 (12) | −0.0054 (9) |
| C7 | 0.0482 (11) | 0.0377 (10) | 0.0378 (10) | 0.0006 (8) | −0.0085 (9) | −0.0055 (8) |
| C8 | 0.0470 (11) | 0.0349 (9) | 0.0367 (10) | −0.0014 (8) | −0.0108 (8) | −0.0048 (7) |
| C9 | 0.0435 (10) | 0.0352 (9) | 0.0349 (9) | 0.0020 (8) | −0.0096 (8) | −0.0046 (7) |
| C10 | 0.0501 (12) | 0.0476 (12) | 0.0379 (10) | −0.0016 (9) | −0.0074 (9) | −0.0051 (9) |
| C11 | 0.0588 (14) | 0.0557 (13) | 0.0393 (11) | 0.0059 (11) | −0.0081 (10) | −0.0143 (10) |
| C12 | 0.0738 (17) | 0.0448 (12) | 0.0515 (13) | −0.0005 (11) | −0.0141 (12) | −0.0183 (10) |
| C13 | 0.0666 (15) | 0.0386 (11) | 0.0517 (13) | −0.0078 (10) | −0.0130 (11) | −0.0074 (9) |
| C14 | 0.0467 (11) | 0.0357 (10) | 0.0373 (10) | 0.0005 (8) | −0.0099 (8) | −0.0045 (8) |
| C15 | 0.0730 (15) | 0.0533 (14) | 0.0440 (12) | −0.0058 (11) | 0.0002 (9) | −0.0152 (10) |
| C16 | 0.0666 (18) | 0.097 (2) | 0.0486 (15) | 0.0153 (16) | 0.0053 (13) | −0.0143 (15) |
| C17 | 0.0561 (13) | 0.0395 (11) | 0.0464 (12) | −0.0060 (9) | −0.0160 (10) | −0.0033 (9) |
| C18 | 0.0631 (16) | 0.0593 (16) | 0.096 (2) | −0.0238 (13) | −0.0233 (16) | 0.0205 (15) |
| C19 | 0.065 (2) | 0.128 (3) | 0.105 (3) | −0.030 (2) | −0.0010 (19) | 0.048 (3) |
| Br1—C15 | 1.914 (3) | C7—C15 | 1.484 (3) |
| Br1A—C15 | 1.9152 (10) | C8—C9 | 1.439 (3) |
| S1—O2 | 1.417 (2) | C8—C17 | 1.472 (3) |
| S1—O1 | 1.419 (2) | C9—C14 | 1.389 (3) |
| S1—N1 | 1.6862 (19) | C9—C10 | 1.405 (3) |
| S1—C1 | 1.751 (2) | C10—C11 | 1.379 (3) |
| O3—C11 | 1.370 (3) | C10—H10 | 0.9300 |
| O3—C16 | 1.407 (4) | C11—C12 | 1.390 (4) |
| O4—C17 | 1.320 (3) | C12—C13 | 1.362 (4) |
| O4—C18 | 1.448 (3) | C12—H12 | 0.9300 |
| O5—C17 | 1.208 (3) | C13—C14 | 1.398 (3) |
| N1—C7 | 1.405 (3) | C13—H13 | 0.9300 |
| N1—C14 | 1.417 (3) | C15—H15A | 0.9700 |
| C1—C6 | 1.372 (3) | C15—H15B | 0.9700 |
| C1—C2 | 1.381 (3) | C15—H15C | 0.9700 |
| C2—C3 | 1.371 (4) | C15—H15D | 0.9700 |
| C2—H2 | 0.9300 | C16—H16A | 0.9600 |
| C3—C4 | 1.369 (4) | C16—H16B | 0.9600 |
| C3—H3 | 0.9300 | C16—H16C | 0.9600 |
| C4—C5 | 1.365 (5) | C18—C19 | 1.487 (5) |
| C4—H4 | 0.9300 | C18—H18A | 0.9700 |
| C5—C6 | 1.388 (4) | C18—H18B | 0.9700 |
| C5—H5 | 0.9300 | C19—H19A | 0.9600 |
| C6—H6 | 0.9300 | C19—H19B | 0.9600 |
| C7—C8 | 1.364 (3) | C19—H19C | 0.9600 |
| O2—S1—O1 | 120.09 (13) | C11—C12—H12 | 119.1 |
| O2—S1—N1 | 106.72 (11) | C12—C13—C14 | 117.7 (2) |
| O1—S1—N1 | 105.29 (11) | C12—C13—H13 | 121.1 |
| O2—S1—C1 | 109.30 (12) | C14—C13—H13 | 121.1 |
| O1—S1—C1 | 108.93 (11) | C9—C14—C13 | 121.2 (2) |
| N1—S1—C1 | 105.49 (10) | C9—C14—N1 | 107.98 (17) |
| C11—O3—C16 | 117.9 (2) | C13—C14—N1 | 130.8 (2) |
| C17—O4—C18 | 117.3 (2) | C7—C15—Br1 | 114.7 (2) |
| C7—N1—C14 | 107.77 (17) | C7—C15—Br1A | 103.7 (4) |
| C7—N1—S1 | 127.88 (15) | C7—C15—H15A | 108.6 |
| C14—N1—S1 | 124.15 (15) | Br1—C15—H15A | 108.6 |
| C6—C1—C2 | 121.7 (2) | Br1A—C15—H15A | 111.8 |
| C6—C1—S1 | 119.67 (19) | C7—C15—H15B | 108.6 |
| C2—C1—S1 | 118.53 (18) | Br1—C15—H15B | 108.6 |
| C3—C2—C1 | 118.6 (2) | Br1A—C15—H15B | 116.3 |
| C3—C2—H2 | 120.7 | H15A—C15—H15B | 107.6 |
| C1—C2—H2 | 120.7 | C7—C15—H15C | 111.1 |
| C4—C3—C2 | 120.6 (3) | Br1—C15—H15C | 107.3 |
| C4—C3—H3 | 119.7 | Br1A—C15—H15C | 111.0 |
| C2—C3—H3 | 119.7 | H15B—C15—H15C | 106.2 |
| C5—C4—C3 | 120.4 (3) | C7—C15—H15D | 111.1 |
| C5—C4—H4 | 119.8 | Br1—C15—H15D | 102.7 |
| C3—C4—H4 | 119.8 | Br1A—C15—H15D | 110.4 |
| C4—C5—C6 | 120.3 (3) | H15A—C15—H15D | 111.1 |
| C4—C5—H5 | 119.8 | H15C—C15—H15D | 109.5 |
| C6—C5—H5 | 119.8 | O3—C16—H16A | 109.5 |
| C1—C6—C5 | 118.4 (3) | O3—C16—H16B | 109.5 |
| C1—C6—H6 | 120.8 | H16A—C16—H16B | 109.5 |
| C5—C6—H6 | 120.8 | O3—C16—H16C | 109.5 |
| C8—C7—N1 | 108.66 (18) | H16A—C16—H16C | 109.5 |
| C8—C7—C15 | 127.3 (2) | H16B—C16—H16C | 109.5 |
| N1—C7—C15 | 124.1 (2) | O5—C17—O4 | 123.3 (2) |
| C7—C8—C9 | 108.47 (18) | O5—C17—C8 | 124.7 (2) |
| C7—C8—C17 | 124.5 (2) | O4—C17—C8 | 112.02 (19) |
| C9—C8—C17 | 127.0 (2) | O4—C18—C19 | 107.3 (3) |
| C14—C9—C10 | 120.41 (19) | O4—C18—H18A | 110.3 |
| C14—C9—C8 | 107.12 (18) | C19—C18—H18A | 110.3 |
| C10—C9—C8 | 132.5 (2) | O4—C18—H18B | 110.3 |
| C11—C10—C9 | 117.5 (2) | C19—C18—H18B | 110.3 |
| C11—C10—H10 | 121.2 | H18A—C18—H18B | 108.5 |
| C9—C10—H10 | 121.2 | C18—C19—H19A | 109.5 |
| O3—C11—C10 | 123.9 (2) | C18—C19—H19B | 109.5 |
| O3—C11—C12 | 114.8 (2) | H19A—C19—H19B | 109.5 |
| C10—C11—C12 | 121.3 (2) | C18—C19—H19C | 109.5 |
| C13—C12—C11 | 121.8 (2) | H19A—C19—H19C | 109.5 |
| C13—C12—H12 | 119.1 | H19B—C19—H19C | 109.5 |
| O2—S1—N1—C7 | −30.0 (2) | C17—C8—C9—C10 | 1.3 (4) |
| O1—S1—N1—C7 | −158.62 (19) | C14—C9—C10—C11 | 0.3 (3) |
| C1—S1—N1—C7 | 86.2 (2) | C8—C9—C10—C11 | 178.5 (2) |
| O2—S1—N1—C14 | 155.94 (18) | C16—O3—C11—C10 | −6.6 (4) |
| O1—S1—N1—C14 | 27.3 (2) | C16—O3—C11—C12 | 174.3 (2) |
| C1—S1—N1—C14 | −87.87 (18) | C9—C10—C11—O3 | −179.0 (2) |
| O2—S1—C1—C6 | 8.6 (2) | C9—C10—C11—C12 | 0.0 (3) |
| O1—S1—C1—C6 | 141.6 (2) | O3—C11—C12—C13 | 179.0 (2) |
| N1—S1—C1—C6 | −105.8 (2) | C10—C11—C12—C13 | −0.1 (4) |
| O2—S1—C1—C2 | −168.24 (19) | C11—C12—C13—C14 | −0.1 (4) |
| O1—S1—C1—C2 | −35.3 (2) | C10—C9—C14—C13 | −0.5 (3) |
| N1—S1—C1—C2 | 77.3 (2) | C8—C9—C14—C13 | −179.1 (2) |
| C6—C1—C2—C3 | 1.4 (4) | C10—C9—C14—N1 | 178.12 (19) |
| S1—C1—C2—C3 | 178.2 (2) | C8—C9—C14—N1 | −0.5 (2) |
| C1—C2—C3—C4 | 0.1 (4) | C12—C13—C14—C9 | 0.4 (3) |
| C2—C3—C4—C5 | −0.9 (5) | C12—C13—C14—N1 | −177.8 (2) |
| C3—C4—C5—C6 | 0.2 (5) | C7—N1—C14—C9 | 0.6 (2) |
| C2—C1—C6—C5 | −2.1 (4) | S1—N1—C14—C9 | 175.69 (14) |
| S1—C1—C6—C5 | −178.8 (2) | C7—N1—C14—C13 | 179.0 (2) |
| C4—C5—C6—C1 | 1.2 (4) | S1—N1—C14—C13 | −5.9 (3) |
| C14—N1—C7—C8 | −0.4 (2) | C8—C7—C15—Br1 | 90.2 (3) |
| S1—N1—C7—C8 | −175.24 (15) | N1—C7—C15—Br1 | −90.1 (2) |
| C14—N1—C7—C15 | 179.9 (2) | C8—C7—C15—Br1A | 87.5 (3) |
| S1—N1—C7—C15 | 5.0 (3) | N1—C7—C15—Br1A | −92.8 (3) |
| N1—C7—C8—C9 | 0.0 (2) | C18—O4—C17—O5 | 2.9 (4) |
| C15—C7—C8—C9 | 179.8 (2) | C18—O4—C17—C8 | −177.4 (2) |
| N1—C7—C8—C17 | −179.39 (19) | C7—C8—C17—O5 | 2.7 (4) |
| C15—C7—C8—C17 | 0.4 (4) | C9—C8—C17—O5 | −176.6 (2) |
| C7—C8—C9—C14 | 0.3 (2) | C7—C8—C17—O4 | −176.9 (2) |
| C17—C8—C9—C14 | 179.7 (2) | C9—C8—C17—O4 | 3.8 (3) |
| C7—C8—C9—C10 | −178.1 (2) | C17—O4—C18—C19 | 171.9 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12···O1i | 0.93 | 2.56 | 3.472 (3) | 165 |
| C2—H2···O5ii | 0.93 | 2.60 | 3.235 (3) | 126 |
| C6—H6···O2 | 0.93 | 2.54 | 2.908 (4) | 104 |
| C10—H10···O4 | 0.93 | 2.37 | 2.892 (3) | 116 |
| C13—H13···O1 | 0.93 | 2.28 | 2.863 (3) | 120 |
| C15—H15A···O5 | 0.97 | 2.31 | 2.911 (4) | 119 |
| C15—H15D···O2 | 0.97 | 2.16 | 2.895 (4) | 131 |
| Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y+1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12···O1i | 0.93 | 2.56 | 3.472 (3) | 165 |
| C2—H2···O5ii | 0.93 | 2.60 | 3.235 (3) | 126 |
| C6—H6···O2 | 0.93 | 2.54 | 2.908 (4) | 104 |
| C10—H10···O4 | 0.93 | 2.37 | 2.892 (3) | 116 |
| C13—H13···O1 | 0.93 | 2.28 | 2.863 (3) | 120 |
| C15—H15A···O5 | 0.97 | 2.31 | 2.911 (4) | 119 |
| C15—H15D···O2 | 0.97 | 2.16 | 2.895 (4) | 131 |
| Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y+1, z. |
The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.
Chakkaravarthi, G., Ramesh, N., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3564.
Nieto, M. J., Alovero, F. L., Manzo, R. H. & Mazzieri, M. R. (2005). Eur. J. Med. Chem. 40, 361–369.
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
Yang, L. M., Lin, S. J., Hsu, F. L. & Yang, T. H. (2002). Bioorg. Med. Chem. Lett. 12, 1013–1015.
In continuation of our studies of benzenesulfonamide derivatives, which are known to exhibit anti–bacterial (Nieto et al., 2005) anti–tumour (Yang et al., 2002) activities, we report the crystal structure of the title compound (I). The geometric parameters of the molecule of I (Fig. 1) agree well with the reported structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008).
The plane of the phenyl ring forms a dihedral angle of 76.99 (6)° with the indole ring system. The N1—S1—C1 plane is orthogonal to indole ring (dihedral angle 88.70 (7)°) and makes 75.97 (9)° with the phenyl ring. The plane of indole ring is almost coplanar (dihedral angle 2.66 (7)°) with the ester group and makes 6.33 (18)° with the methoxy group.
The torsion angles O2–S1–N1–C7 and O1–S1–N1–C14 [-30.0 (2)° and 27.3 (2)°, respectively] indicate syn–conformation of the sulfonyl moiety. The Br1 atom is disordered over two positions with the site occupancy factors of 0.833 (14) and 0.167 (14). The molecular packing is stabilized by weak intramolecular C—H···O interactions and the crystal packing of I (Fig. 2) is stabilized by weak intermolecular C—H···O interactions (see Table).