Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034800/bt2442sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034800/bt2442Isup2.hkl |
CCDC reference: 657810
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C)= 0.004 Å
- R factor = 0.040
- wR factor = 0.115
- Data-to-parameter ratio = 23.4
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
For related literature, see: Kusunoki et al. (2006); Nieto et al. (2005); Liu et al. (2007); Palani et al. (2006). A similiar compound with methoxycarbonyl has been reported (Senthil Kumar et al., 2006).
Ethyl-1-benzenesulfonyl-2-bromomethyl indole-3-carboxylate was prepared via the allylic bromination of ethyl-1-benzenesulfonyl-2-methyl indole-3-carboxylate (3.93 mmol) using N-bromo succiniamide (3.93 mmol) in a catalytic amount of benzoyl peroxide in CCl4 (20 ml) at reflux. The obtained compound was dissolved in hexane and ethyl acetate (9:1). Crystals were grown by slow evaporation of an ethyl acetate solution.
H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å, 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 benzenesulfonamide derivatives possess significant biological activities, such as proliferation of colon adenocarcinoma cells (Kusunoki et al., 2006) and antibacterial (Nieto et al., 2005).
The geometric parameters in the title compound agree with the reported values of similar structures (Liu et al., 2007; Palani et al., 2006). The 5-membered and 6-membered rings of the indole moiety are co-planar [dihedral angle = 0.46 (2)°]. The sum of the bond angles around N1 (359.5°) indicates sp2 hybridization.
The phenyl ring forms a dihedral angle 83.87 (2)° with the indole ring system. The torsion angles C7 - N1 - S1 - O2 and C14 - N1 - S1 - O1 [27.2 (2)° and -36.3 (2)°, respectively] indicate the syn conformation of the sulfonyl moiety.
The details of the hydrogen bonding are given in Table 1. The molecular structure 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.
A similiar compound with methoxycarbonyl has been reported (Senthil Kumar et al., 2006).
For related literature, see: Kusunoki et al. (2006); Nieto et al. (2005); Liu et al. (2007); Palani et al. (2006). A similiar compound with methoxycarbonyl has been reported (Senthil Kumar et al., 2006).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C18H16BrNO4S | F(000) = 856 |
Mr = 422.29 | Dx = 1.574 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6136 reflections |
a = 8.1684 (3) Å | θ = 2.3–24.9° |
b = 9.4962 (4) Å | µ = 2.45 mm−1 |
c = 23.0376 (9) Å | T = 295 K |
β = 94.147 (1)° | Needle, colourless |
V = 1782.32 (12) Å3 | 0.26 × 0.20 × 0.18 mm |
Z = 4 |
Bruker Kappa APEX II diffractometer | 5283 independent reflections |
Radiation source: fine-focus sealed tube | 3029 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω and φ scans | θmax = 30.2°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.527, Tmax = 0.640 | k = −13→13 |
23119 measured reflections | l = −32→32 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0502P)2 + 0.431P] where P = (Fo2 + 2Fc2)/3 |
5283 reflections | (Δ/σ)max = 0.002 |
226 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
C18H16BrNO4S | V = 1782.32 (12) Å3 |
Mr = 422.29 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.1684 (3) Å | µ = 2.45 mm−1 |
b = 9.4962 (4) Å | T = 295 K |
c = 23.0376 (9) Å | 0.26 × 0.20 × 0.18 mm |
β = 94.147 (1)° |
Bruker Kappa APEX II diffractometer | 5283 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3029 reflections with I > 2σ(I) |
Tmin = 0.527, Tmax = 0.640 | Rint = 0.037 |
23119 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.43 e Å−3 |
5283 reflections | Δρmin = −0.51 e Å−3 |
226 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2387 (3) | 0.2446 (3) | 0.68219 (9) | 0.0461 (5) | |
C2 | 0.2765 (3) | 0.3652 (3) | 0.71316 (11) | 0.0589 (6) | |
H2 | 0.3853 | 0.3907 | 0.7222 | 0.071* | |
C3 | 0.1510 (4) | 0.4474 (3) | 0.73057 (13) | 0.0747 (8) | |
H3 | 0.1748 | 0.5289 | 0.7519 | 0.090* | |
C4 | −0.0089 (4) | 0.4103 (3) | 0.71671 (13) | 0.0739 (8) | |
H4 | −0.0932 | 0.4660 | 0.7292 | 0.089* | |
C5 | −0.0456 (3) | 0.2918 (3) | 0.68459 (13) | 0.0699 (8) | |
H5 | −0.1546 | 0.2690 | 0.6743 | 0.084* | |
C6 | 0.0785 (3) | 0.2060 (3) | 0.66739 (12) | 0.0590 (6) | |
H6 | 0.0545 | 0.1241 | 0.6463 | 0.071* | |
C7 | 0.2583 (3) | −0.0606 (3) | 0.59266 (11) | 0.0548 (6) | |
C8 | 0.2107 (4) | −0.1621 (3) | 0.63136 (14) | 0.0756 (8) | |
H8 | 0.2394 | −0.1554 | 0.6711 | 0.091* | |
C9 | 0.1188 (4) | −0.2737 (4) | 0.60822 (19) | 0.0861 (10) | |
H9 | 0.0865 | −0.3439 | 0.6331 | 0.103* | |
C10 | 0.0738 (4) | −0.2844 (3) | 0.55022 (18) | 0.0802 (9) | |
H10 | 0.0090 | −0.3598 | 0.5367 | 0.096* | |
C11 | 0.1223 (3) | −0.1862 (3) | 0.51146 (14) | 0.0658 (7) | |
H11 | 0.0935 | −0.1955 | 0.4718 | 0.079* | |
C12 | 0.2166 (3) | −0.0711 (2) | 0.53288 (11) | 0.0518 (6) | |
C13 | 0.2853 (3) | 0.0485 (2) | 0.50541 (10) | 0.0472 (5) | |
C14 | 0.3655 (3) | 0.1301 (3) | 0.54708 (10) | 0.0467 (5) | |
C15 | 0.4574 (3) | 0.2627 (3) | 0.53971 (12) | 0.0589 (6) | |
H15A | 0.5022 | 0.2631 | 0.5019 | 0.071* | |
H15B | 0.5481 | 0.2683 | 0.5692 | 0.071* | |
C16 | 0.2679 (3) | 0.0703 (3) | 0.44194 (11) | 0.0565 (6) | |
C17 | 0.3131 (4) | 0.2231 (4) | 0.36344 (11) | 0.0755 (9) | |
H17A | 0.2003 | 0.2113 | 0.3479 | 0.091* | |
H17B | 0.3820 | 0.1598 | 0.3429 | 0.091* | |
C18 | 0.3658 (5) | 0.3693 (5) | 0.35624 (15) | 0.1081 (13) | |
H18A | 0.3578 | 0.3931 | 0.3156 | 0.162* | |
H18B | 0.4774 | 0.3796 | 0.3717 | 0.162* | |
H18C | 0.2966 | 0.4309 | 0.3767 | 0.162* | |
N1 | 0.3515 (2) | 0.0648 (2) | 0.60141 (8) | 0.0529 (5) | |
O1 | 0.5447 (2) | 0.2186 (3) | 0.66281 (9) | 0.0900 (8) | |
O2 | 0.4074 (3) | 0.0190 (3) | 0.70652 (8) | 0.0897 (7) | |
O3 | 0.2063 (3) | −0.0149 (2) | 0.40830 (9) | 0.0834 (6) | |
O4 | 0.3275 (2) | 0.1922 (2) | 0.42551 (7) | 0.0658 (5) | |
S1 | 0.40267 (8) | 0.13478 (9) | 0.66717 (3) | 0.0608 (2) | |
Br1 | 0.31355 (4) | 0.42658 (3) | 0.546316 (14) | 0.07439 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0396 (11) | 0.0612 (14) | 0.0374 (11) | 0.0051 (10) | 0.0012 (9) | −0.0013 (10) |
C2 | 0.0543 (14) | 0.0657 (15) | 0.0552 (14) | −0.0019 (13) | −0.0056 (12) | −0.0089 (13) |
C3 | 0.094 (2) | 0.0675 (18) | 0.0618 (17) | 0.0152 (16) | −0.0029 (16) | −0.0147 (14) |
C4 | 0.073 (2) | 0.081 (2) | 0.0690 (18) | 0.0306 (16) | 0.0164 (15) | 0.0056 (16) |
C5 | 0.0412 (13) | 0.084 (2) | 0.085 (2) | 0.0091 (13) | 0.0078 (13) | 0.0100 (17) |
C6 | 0.0432 (13) | 0.0621 (15) | 0.0710 (16) | −0.0007 (11) | −0.0006 (12) | −0.0062 (13) |
C7 | 0.0471 (13) | 0.0575 (14) | 0.0597 (15) | 0.0160 (11) | 0.0036 (11) | −0.0021 (12) |
C8 | 0.0763 (19) | 0.076 (2) | 0.0755 (19) | 0.0153 (16) | 0.0082 (15) | 0.0103 (16) |
C9 | 0.077 (2) | 0.0643 (19) | 0.119 (3) | 0.0090 (16) | 0.020 (2) | 0.023 (2) |
C10 | 0.0606 (17) | 0.0526 (16) | 0.127 (3) | 0.0066 (13) | 0.0039 (18) | −0.0018 (18) |
C11 | 0.0529 (15) | 0.0556 (15) | 0.087 (2) | 0.0102 (12) | −0.0040 (14) | −0.0149 (14) |
C12 | 0.0408 (12) | 0.0511 (13) | 0.0630 (15) | 0.0150 (10) | 0.0009 (11) | −0.0110 (11) |
C13 | 0.0395 (11) | 0.0520 (13) | 0.0498 (13) | 0.0120 (9) | 0.0006 (10) | −0.0119 (10) |
C14 | 0.0369 (11) | 0.0558 (13) | 0.0474 (13) | 0.0120 (10) | 0.0032 (9) | −0.0105 (10) |
C15 | 0.0478 (13) | 0.0648 (15) | 0.0641 (15) | 0.0025 (12) | 0.0034 (11) | −0.0143 (13) |
C16 | 0.0504 (14) | 0.0670 (16) | 0.0521 (14) | 0.0143 (12) | 0.0035 (11) | −0.0147 (13) |
C17 | 0.0757 (19) | 0.106 (2) | 0.0452 (15) | 0.0131 (17) | 0.0034 (13) | −0.0012 (15) |
C18 | 0.134 (4) | 0.125 (3) | 0.064 (2) | −0.018 (3) | −0.002 (2) | 0.023 (2) |
N1 | 0.0481 (11) | 0.0638 (12) | 0.0461 (11) | 0.0088 (9) | −0.0015 (9) | −0.0099 (9) |
O1 | 0.0357 (9) | 0.160 (2) | 0.0733 (12) | −0.0026 (12) | −0.0043 (8) | −0.0447 (14) |
O2 | 0.1038 (16) | 0.1094 (17) | 0.0528 (11) | 0.0539 (14) | −0.0144 (11) | −0.0001 (11) |
O3 | 0.1037 (16) | 0.0862 (14) | 0.0584 (12) | −0.0081 (13) | −0.0063 (11) | −0.0274 (11) |
O4 | 0.0751 (12) | 0.0783 (13) | 0.0436 (9) | −0.0006 (10) | 0.0008 (8) | −0.0060 (9) |
S1 | 0.0430 (3) | 0.0916 (5) | 0.0460 (3) | 0.0190 (3) | −0.0092 (3) | −0.0135 (3) |
Br1 | 0.0816 (2) | 0.05670 (18) | 0.0855 (2) | 0.00656 (14) | 0.01067 (16) | −0.00998 (14) |
C1—C2 | 1.373 (3) | C11—H11 | 0.9300 |
C1—C6 | 1.378 (3) | C12—C13 | 1.434 (3) |
C1—S1 | 1.752 (2) | C13—C14 | 1.364 (3) |
C2—C3 | 1.371 (4) | C13—C16 | 1.473 (3) |
C2—H2 | 0.9300 | C14—N1 | 1.409 (3) |
C3—C4 | 1.368 (5) | C14—C15 | 1.482 (4) |
C3—H3 | 0.9300 | C15—Br1 | 1.962 (2) |
C4—C5 | 1.368 (4) | C15—H15A | 0.9700 |
C4—H4 | 0.9300 | C15—H15B | 0.9700 |
C5—C6 | 1.381 (4) | C16—O3 | 1.205 (3) |
C5—H5 | 0.9300 | C16—O4 | 1.322 (3) |
C6—H6 | 0.9300 | C17—O4 | 1.456 (3) |
C7—C8 | 1.388 (4) | C17—C18 | 1.467 (5) |
C7—C12 | 1.398 (4) | C17—H17A | 0.9700 |
C7—N1 | 1.420 (3) | C17—H17B | 0.9700 |
C8—C9 | 1.383 (5) | C18—H18A | 0.9600 |
C8—H8 | 0.9300 | C18—H18B | 0.9600 |
C9—C10 | 1.364 (5) | C18—H18C | 0.9600 |
C9—H9 | 0.9300 | N1—S1 | 1.679 (2) |
C10—C11 | 1.370 (4) | O1—S1 | 1.416 (2) |
C10—H10 | 0.9300 | O2—S1 | 1.424 (3) |
C11—C12 | 1.406 (4) | ||
C2—C1—C6 | 121.6 (2) | C14—C13—C16 | 128.8 (2) |
C2—C1—S1 | 116.92 (18) | C12—C13—C16 | 122.4 (2) |
C6—C1—S1 | 121.26 (19) | C13—C14—N1 | 108.1 (2) |
C3—C2—C1 | 118.8 (2) | C13—C14—C15 | 128.6 (2) |
C3—C2—H2 | 120.6 | N1—C14—C15 | 123.4 (2) |
C1—C2—H2 | 120.6 | C14—C15—Br1 | 110.73 (16) |
C4—C3—C2 | 120.4 (3) | C14—C15—H15A | 109.5 |
C4—C3—H3 | 119.8 | Br1—C15—H15A | 109.5 |
C2—C3—H3 | 119.8 | C14—C15—H15B | 109.5 |
C3—C4—C5 | 120.4 (3) | Br1—C15—H15B | 109.5 |
C3—C4—H4 | 119.8 | H15A—C15—H15B | 108.1 |
C5—C4—H4 | 119.8 | O3—C16—O4 | 123.3 (3) |
C4—C5—C6 | 120.3 (3) | O3—C16—C13 | 123.4 (3) |
C4—C5—H5 | 119.9 | O4—C16—C13 | 113.3 (2) |
C6—C5—H5 | 119.9 | O4—C17—C18 | 107.4 (3) |
C1—C6—C5 | 118.4 (3) | O4—C17—H17A | 110.2 |
C1—C6—H6 | 120.8 | C18—C17—H17A | 110.2 |
C5—C6—H6 | 120.8 | O4—C17—H17B | 110.2 |
C8—C7—C12 | 121.6 (3) | C18—C17—H17B | 110.2 |
C8—C7—N1 | 131.6 (3) | H17A—C17—H17B | 108.5 |
C12—C7—N1 | 106.8 (2) | C17—C18—H18A | 109.5 |
C9—C8—C7 | 117.0 (3) | C17—C18—H18B | 109.5 |
C9—C8—H8 | 121.5 | H18A—C18—H18B | 109.5 |
C7—C8—H8 | 121.5 | C17—C18—H18C | 109.5 |
C10—C9—C8 | 122.4 (3) | H18A—C18—H18C | 109.5 |
C10—C9—H9 | 118.8 | H18B—C18—H18C | 109.5 |
C8—C9—H9 | 118.8 | C14—N1—C7 | 108.65 (19) |
C9—C10—C11 | 121.2 (3) | C14—N1—S1 | 126.64 (17) |
C9—C10—H10 | 119.4 | C7—N1—S1 | 123.76 (18) |
C11—C10—H10 | 119.4 | C16—O4—C17 | 116.9 (2) |
C10—C11—C12 | 118.6 (3) | O1—S1—O2 | 119.62 (14) |
C10—C11—H11 | 120.7 | O1—S1—N1 | 108.05 (12) |
C12—C11—H11 | 120.7 | O2—S1—N1 | 105.23 (13) |
C7—C12—C11 | 119.3 (3) | O1—S1—C1 | 108.76 (13) |
C7—C12—C13 | 107.6 (2) | O2—S1—C1 | 108.65 (12) |
C11—C12—C13 | 133.1 (2) | N1—S1—C1 | 105.66 (10) |
C14—C13—C12 | 108.8 (2) | ||
C6—C1—C2—C3 | 1.2 (4) | N1—C14—C15—Br1 | −89.9 (2) |
S1—C1—C2—C3 | −174.0 (2) | C14—C13—C16—O3 | 173.3 (2) |
C1—C2—C3—C4 | −0.7 (4) | C12—C13—C16—O3 | −5.8 (4) |
C2—C3—C4—C5 | −0.9 (5) | C14—C13—C16—O4 | −6.3 (3) |
C3—C4—C5—C6 | 2.0 (5) | C12—C13—C16—O4 | 174.6 (2) |
C2—C1—C6—C5 | −0.1 (4) | C13—C14—N1—C7 | −0.5 (2) |
S1—C1—C6—C5 | 174.9 (2) | C15—C14—N1—C7 | −179.0 (2) |
C4—C5—C6—C1 | −1.5 (4) | C13—C14—N1—S1 | −169.61 (16) |
C12—C7—C8—C9 | −0.6 (4) | C15—C14—N1—S1 | 11.9 (3) |
N1—C7—C8—C9 | −179.9 (3) | C8—C7—N1—C14 | 179.6 (3) |
C7—C8—C9—C10 | −0.8 (5) | C12—C7—N1—C14 | 0.2 (2) |
C8—C9—C10—C11 | 2.0 (5) | C8—C7—N1—S1 | −10.9 (4) |
C9—C10—C11—C12 | −1.7 (4) | C12—C7—N1—S1 | 169.74 (16) |
C8—C7—C12—C11 | 0.9 (3) | O3—C16—O4—C17 | 1.3 (4) |
N1—C7—C12—C11 | −179.7 (2) | C13—C16—O4—C17 | −179.1 (2) |
C8—C7—C12—C13 | −179.4 (2) | C18—C17—O4—C16 | 172.4 (3) |
N1—C7—C12—C13 | 0.1 (2) | C14—N1—S1—O1 | −36.3 (2) |
C10—C11—C12—C7 | 0.3 (3) | C7—N1—S1—O1 | 156.06 (19) |
C10—C11—C12—C13 | −179.5 (2) | C14—N1—S1—O2 | −165.21 (19) |
C7—C12—C13—C14 | −0.4 (2) | C7—N1—S1—O2 | 27.2 (2) |
C11—C12—C13—C14 | 179.3 (2) | C14—N1—S1—C1 | 79.9 (2) |
C7—C12—C13—C16 | 178.8 (2) | C7—N1—S1—C1 | −87.67 (19) |
C11—C12—C13—C16 | −1.4 (4) | C2—C1—S1—O1 | −29.9 (2) |
C12—C13—C14—N1 | 0.5 (2) | C6—C1—S1—O1 | 154.9 (2) |
C16—C13—C14—N1 | −178.7 (2) | C2—C1—S1—O2 | 101.9 (2) |
C12—C13—C14—C15 | 179.0 (2) | C6—C1—S1—O2 | −73.4 (2) |
C16—C13—C14—C15 | −0.2 (4) | C2—C1—S1—N1 | −145.64 (19) |
C13—C14—C15—Br1 | 91.9 (3) | C6—C1—S1—N1 | 39.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2i | 0.93 | 2.58 | 3.396 (3) | 147 |
C5—H5···O1ii | 0.93 | 2.50 | 3.419 (3) | 171 |
C2—H2···O1 | 0.93 | 2.55 | 2.907 (3) | 103 |
C8—H8···O2 | 0.93 | 2.27 | 2.852 (4) | 121 |
C11—H11···O3 | 0.93 | 2.48 | 3.000 (4) | 116 |
C15—H15A···O4 | 0.97 | 2.28 | 2.845 (3) | 116 |
C15—H15B···O1 | 0.97 | 2.21 | 2.904 (3) | 128 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C18H16BrNO4S |
Mr | 422.29 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 8.1684 (3), 9.4962 (4), 23.0376 (9) |
β (°) | 94.147 (1) |
V (Å3) | 1782.32 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.45 |
Crystal size (mm) | 0.26 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker Kappa APEX II |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.527, 0.640 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23119, 5283, 3029 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.707 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.115, 1.00 |
No. of reflections | 5283 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.51 |
Computer programs: APEX2 (Bruker, 2004), APEX2, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2i | 0.93 | 2.58 | 3.396 (3) | 146.9 |
C5—H5···O1ii | 0.93 | 2.50 | 3.419 (3) | 170.9 |
C2—H2···O1 | 0.93 | 2.55 | 2.907 (3) | 103 |
C8—H8···O2 | 0.93 | 2.27 | 2.852 (4) | 121 |
C11—H11···O3 | 0.93 | 2.48 | 3.000 (4) | 116 |
C15—H15A···O4 | 0.97 | 2.28 | 2.845 (3) | 116 |
C15—H15B···O1 | 0.97 | 2.21 | 2.904 (3) | 128 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z. |
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The benzenesulfonamide derivatives possess significant biological activities, such as proliferation of colon adenocarcinoma cells (Kusunoki et al., 2006) and antibacterial (Nieto et al., 2005).
The geometric parameters in the title compound agree with the reported values of similar structures (Liu et al., 2007; Palani et al., 2006). The 5-membered and 6-membered rings of the indole moiety are co-planar [dihedral angle = 0.46 (2)°]. The sum of the bond angles around N1 (359.5°) indicates sp2 hybridization.
The phenyl ring forms a dihedral angle 83.87 (2)° with the indole ring system. The torsion angles C7 - N1 - S1 - O2 and C14 - N1 - S1 - O1 [27.2 (2)° and -36.3 (2)°, respectively] indicate the syn conformation of the sulfonyl moiety.
The details of the hydrogen bonding are given in Table 1. The molecular structure 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.
A similiar compound with methoxycarbonyl has been reported (Senthil Kumar et al., 2006).