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In the title compound, C18H16BrNO4S, the phenyl ring forms a dihedral angle of 83.87 (2)° with the indole ring system. The mol­ecular structure is stabilized by weak intra­molecular C—H...O inter­actions and the crystal packing is stabilized by weak inter­molecular C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034800/bt2442sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034800/bt2442Isup2.hkl
Contains datablock I

CCDC reference: 657810

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

Comment top

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).

Related literature top

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).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
Ethyl 2-bromomethyl-1-phenylsulfonyl-1H-indole-3-carboxylate top
Crystal data top
C18H16BrNO4SF(000) = 856
Mr = 422.29Dx = 1.574 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6136 reflections
a = 8.1684 (3) Åθ = 2.3–24.9°
b = 9.4962 (4) ŵ = 2.45 mm1
c = 23.0376 (9) ÅT = 295 K
β = 94.147 (1)°Needle, colourless
V = 1782.32 (12) Å30.26 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker Kappa APEX II
diffractometer
5283 independent reflections
Radiation source: fine-focus sealed tube3029 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω and φ scansθmax = 30.2°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.527, Tmax = 0.640k = 1313
23119 measured reflectionsl = 3232
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-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 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.51 e Å3
Crystal data top
C18H16BrNO4SV = 1782.32 (12) Å3
Mr = 422.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.1684 (3) ŵ = 2.45 mm1
b = 9.4962 (4) ÅT = 295 K
c = 23.0376 (9) Å0.26 × 0.20 × 0.18 mm
β = 94.147 (1)°
Data collection top
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 = 0.640Rint = 0.037
23119 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.00Δρmax = 0.43 e Å3
5283 reflectionsΔρmin = 0.51 e Å3
226 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2387 (3)0.2446 (3)0.68219 (9)0.0461 (5)
C20.2765 (3)0.3652 (3)0.71316 (11)0.0589 (6)
H20.38530.39070.72220.071*
C30.1510 (4)0.4474 (3)0.73057 (13)0.0747 (8)
H30.17480.52890.75190.090*
C40.0089 (4)0.4103 (3)0.71671 (13)0.0739 (8)
H40.09320.46600.72920.089*
C50.0456 (3)0.2918 (3)0.68459 (13)0.0699 (8)
H50.15460.26900.67430.084*
C60.0785 (3)0.2060 (3)0.66739 (12)0.0590 (6)
H60.05450.12410.64630.071*
C70.2583 (3)0.0606 (3)0.59266 (11)0.0548 (6)
C80.2107 (4)0.1621 (3)0.63136 (14)0.0756 (8)
H80.23940.15540.67110.091*
C90.1188 (4)0.2737 (4)0.60822 (19)0.0861 (10)
H90.08650.34390.63310.103*
C100.0738 (4)0.2844 (3)0.55022 (18)0.0802 (9)
H100.00900.35980.53670.096*
C110.1223 (3)0.1862 (3)0.51146 (14)0.0658 (7)
H110.09350.19550.47180.079*
C120.2166 (3)0.0711 (2)0.53288 (11)0.0518 (6)
C130.2853 (3)0.0485 (2)0.50541 (10)0.0472 (5)
C140.3655 (3)0.1301 (3)0.54708 (10)0.0467 (5)
C150.4574 (3)0.2627 (3)0.53971 (12)0.0589 (6)
H15A0.50220.26310.50190.071*
H15B0.54810.26830.56920.071*
C160.2679 (3)0.0703 (3)0.44194 (11)0.0565 (6)
C170.3131 (4)0.2231 (4)0.36344 (11)0.0755 (9)
H17A0.20030.21130.34790.091*
H17B0.38200.15980.34290.091*
C180.3658 (5)0.3693 (5)0.35624 (15)0.1081 (13)
H18A0.35780.39310.31560.162*
H18B0.47740.37960.37170.162*
H18C0.29660.43090.37670.162*
N10.3515 (2)0.0648 (2)0.60141 (8)0.0529 (5)
O10.5447 (2)0.2186 (3)0.66281 (9)0.0900 (8)
O20.4074 (3)0.0190 (3)0.70652 (8)0.0897 (7)
O30.2063 (3)0.0149 (2)0.40830 (9)0.0834 (6)
O40.3275 (2)0.1922 (2)0.42551 (7)0.0658 (5)
S10.40267 (8)0.13478 (9)0.66717 (3)0.0608 (2)
Br10.31355 (4)0.42658 (3)0.546316 (14)0.07439 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0396 (11)0.0612 (14)0.0374 (11)0.0051 (10)0.0012 (9)0.0013 (10)
C20.0543 (14)0.0657 (15)0.0552 (14)0.0019 (13)0.0056 (12)0.0089 (13)
C30.094 (2)0.0675 (18)0.0618 (17)0.0152 (16)0.0029 (16)0.0147 (14)
C40.073 (2)0.081 (2)0.0690 (18)0.0306 (16)0.0164 (15)0.0056 (16)
C50.0412 (13)0.084 (2)0.085 (2)0.0091 (13)0.0078 (13)0.0100 (17)
C60.0432 (13)0.0621 (15)0.0710 (16)0.0007 (11)0.0006 (12)0.0062 (13)
C70.0471 (13)0.0575 (14)0.0597 (15)0.0160 (11)0.0036 (11)0.0021 (12)
C80.0763 (19)0.076 (2)0.0755 (19)0.0153 (16)0.0082 (15)0.0103 (16)
C90.077 (2)0.0643 (19)0.119 (3)0.0090 (16)0.020 (2)0.023 (2)
C100.0606 (17)0.0526 (16)0.127 (3)0.0066 (13)0.0039 (18)0.0018 (18)
C110.0529 (15)0.0556 (15)0.087 (2)0.0102 (12)0.0040 (14)0.0149 (14)
C120.0408 (12)0.0511 (13)0.0630 (15)0.0150 (10)0.0009 (11)0.0110 (11)
C130.0395 (11)0.0520 (13)0.0498 (13)0.0120 (9)0.0006 (10)0.0119 (10)
C140.0369 (11)0.0558 (13)0.0474 (13)0.0120 (10)0.0032 (9)0.0105 (10)
C150.0478 (13)0.0648 (15)0.0641 (15)0.0025 (12)0.0034 (11)0.0143 (13)
C160.0504 (14)0.0670 (16)0.0521 (14)0.0143 (12)0.0035 (11)0.0147 (13)
C170.0757 (19)0.106 (2)0.0452 (15)0.0131 (17)0.0034 (13)0.0012 (15)
C180.134 (4)0.125 (3)0.064 (2)0.018 (3)0.002 (2)0.023 (2)
N10.0481 (11)0.0638 (12)0.0461 (11)0.0088 (9)0.0015 (9)0.0099 (9)
O10.0357 (9)0.160 (2)0.0733 (12)0.0026 (12)0.0043 (8)0.0447 (14)
O20.1038 (16)0.1094 (17)0.0528 (11)0.0539 (14)0.0144 (11)0.0001 (11)
O30.1037 (16)0.0862 (14)0.0584 (12)0.0081 (13)0.0063 (11)0.0274 (11)
O40.0751 (12)0.0783 (13)0.0436 (9)0.0006 (10)0.0008 (8)0.0060 (9)
S10.0430 (3)0.0916 (5)0.0460 (3)0.0190 (3)0.0092 (3)0.0135 (3)
Br10.0816 (2)0.05670 (18)0.0855 (2)0.00656 (14)0.01067 (16)0.00998 (14)
Geometric parameters (Å, º) top
C1—C21.373 (3)C11—H110.9300
C1—C61.378 (3)C12—C131.434 (3)
C1—S11.752 (2)C13—C141.364 (3)
C2—C31.371 (4)C13—C161.473 (3)
C2—H20.9300C14—N11.409 (3)
C3—C41.368 (5)C14—C151.482 (4)
C3—H30.9300C15—Br11.962 (2)
C4—C51.368 (4)C15—H15A0.9700
C4—H40.9300C15—H15B0.9700
C5—C61.381 (4)C16—O31.205 (3)
C5—H50.9300C16—O41.322 (3)
C6—H60.9300C17—O41.456 (3)
C7—C81.388 (4)C17—C181.467 (5)
C7—C121.398 (4)C17—H17A0.9700
C7—N11.420 (3)C17—H17B0.9700
C8—C91.383 (5)C18—H18A0.9600
C8—H80.9300C18—H18B0.9600
C9—C101.364 (5)C18—H18C0.9600
C9—H90.9300N1—S11.679 (2)
C10—C111.370 (4)O1—S11.416 (2)
C10—H100.9300O2—S11.424 (3)
C11—C121.406 (4)
C2—C1—C6121.6 (2)C14—C13—C16128.8 (2)
C2—C1—S1116.92 (18)C12—C13—C16122.4 (2)
C6—C1—S1121.26 (19)C13—C14—N1108.1 (2)
C3—C2—C1118.8 (2)C13—C14—C15128.6 (2)
C3—C2—H2120.6N1—C14—C15123.4 (2)
C1—C2—H2120.6C14—C15—Br1110.73 (16)
C4—C3—C2120.4 (3)C14—C15—H15A109.5
C4—C3—H3119.8Br1—C15—H15A109.5
C2—C3—H3119.8C14—C15—H15B109.5
C3—C4—C5120.4 (3)Br1—C15—H15B109.5
C3—C4—H4119.8H15A—C15—H15B108.1
C5—C4—H4119.8O3—C16—O4123.3 (3)
C4—C5—C6120.3 (3)O3—C16—C13123.4 (3)
C4—C5—H5119.9O4—C16—C13113.3 (2)
C6—C5—H5119.9O4—C17—C18107.4 (3)
C1—C6—C5118.4 (3)O4—C17—H17A110.2
C1—C6—H6120.8C18—C17—H17A110.2
C5—C6—H6120.8O4—C17—H17B110.2
C8—C7—C12121.6 (3)C18—C17—H17B110.2
C8—C7—N1131.6 (3)H17A—C17—H17B108.5
C12—C7—N1106.8 (2)C17—C18—H18A109.5
C9—C8—C7117.0 (3)C17—C18—H18B109.5
C9—C8—H8121.5H18A—C18—H18B109.5
C7—C8—H8121.5C17—C18—H18C109.5
C10—C9—C8122.4 (3)H18A—C18—H18C109.5
C10—C9—H9118.8H18B—C18—H18C109.5
C8—C9—H9118.8C14—N1—C7108.65 (19)
C9—C10—C11121.2 (3)C14—N1—S1126.64 (17)
C9—C10—H10119.4C7—N1—S1123.76 (18)
C11—C10—H10119.4C16—O4—C17116.9 (2)
C10—C11—C12118.6 (3)O1—S1—O2119.62 (14)
C10—C11—H11120.7O1—S1—N1108.05 (12)
C12—C11—H11120.7O2—S1—N1105.23 (13)
C7—C12—C11119.3 (3)O1—S1—C1108.76 (13)
C7—C12—C13107.6 (2)O2—S1—C1108.65 (12)
C11—C12—C13133.1 (2)N1—S1—C1105.66 (10)
C14—C13—C12108.8 (2)
C6—C1—C2—C31.2 (4)N1—C14—C15—Br189.9 (2)
S1—C1—C2—C3174.0 (2)C14—C13—C16—O3173.3 (2)
C1—C2—C3—C40.7 (4)C12—C13—C16—O35.8 (4)
C2—C3—C4—C50.9 (5)C14—C13—C16—O46.3 (3)
C3—C4—C5—C62.0 (5)C12—C13—C16—O4174.6 (2)
C2—C1—C6—C50.1 (4)C13—C14—N1—C70.5 (2)
S1—C1—C6—C5174.9 (2)C15—C14—N1—C7179.0 (2)
C4—C5—C6—C11.5 (4)C13—C14—N1—S1169.61 (16)
C12—C7—C8—C90.6 (4)C15—C14—N1—S111.9 (3)
N1—C7—C8—C9179.9 (3)C8—C7—N1—C14179.6 (3)
C7—C8—C9—C100.8 (5)C12—C7—N1—C140.2 (2)
C8—C9—C10—C112.0 (5)C8—C7—N1—S110.9 (4)
C9—C10—C11—C121.7 (4)C12—C7—N1—S1169.74 (16)
C8—C7—C12—C110.9 (3)O3—C16—O4—C171.3 (4)
N1—C7—C12—C11179.7 (2)C13—C16—O4—C17179.1 (2)
C8—C7—C12—C13179.4 (2)C18—C17—O4—C16172.4 (3)
N1—C7—C12—C130.1 (2)C14—N1—S1—O136.3 (2)
C10—C11—C12—C70.3 (3)C7—N1—S1—O1156.06 (19)
C10—C11—C12—C13179.5 (2)C14—N1—S1—O2165.21 (19)
C7—C12—C13—C140.4 (2)C7—N1—S1—O227.2 (2)
C11—C12—C13—C14179.3 (2)C14—N1—S1—C179.9 (2)
C7—C12—C13—C16178.8 (2)C7—N1—S1—C187.67 (19)
C11—C12—C13—C161.4 (4)C2—C1—S1—O129.9 (2)
C12—C13—C14—N10.5 (2)C6—C1—S1—O1154.9 (2)
C16—C13—C14—N1178.7 (2)C2—C1—S1—O2101.9 (2)
C12—C13—C14—C15179.0 (2)C6—C1—S1—O273.4 (2)
C16—C13—C14—C150.2 (4)C2—C1—S1—N1145.64 (19)
C13—C14—C15—Br191.9 (3)C6—C1—S1—N139.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.583.396 (3)147
C5—H5···O1ii0.932.503.419 (3)171
C2—H2···O10.932.552.907 (3)103
C8—H8···O20.932.272.852 (4)121
C11—H11···O30.932.483.000 (4)116
C15—H15A···O40.972.282.845 (3)116
C15—H15B···O10.972.212.904 (3)128
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC18H16BrNO4S
Mr422.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)8.1684 (3), 9.4962 (4), 23.0376 (9)
β (°) 94.147 (1)
V3)1782.32 (12)
Z4
Radiation typeMo Kα
µ (mm1)2.45
Crystal size (mm)0.26 × 0.20 × 0.18
Data collection
DiffractometerBruker Kappa APEX II
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.527, 0.640
No. of measured, independent and
observed [I > 2σ(I)] reflections
23119, 5283, 3029
Rint0.037
(sin θ/λ)max1)0.707
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.115, 1.00
No. of reflections5283
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.51

Computer programs: APEX2 (Bruker, 2004), APEX2, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.583.396 (3)146.9
C5—H5···O1ii0.932.503.419 (3)170.9
C2—H2···O10.932.552.907 (3)103
C8—H8···O20.932.272.852 (4)121
C11—H11···O30.932.483.000 (4)116
C15—H15A···O40.972.282.845 (3)116
C15—H15B···O10.972.212.904 (3)128
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x1, y, z.
 

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