supplementary materials


tk5271 scheme

Acta Cryst. (2013). E69, o1784    [ doi:10.1107/S1600536813031073 ]

(E)-1-[2-(4-Chloro-2-nitro­styr­yl)-1-phenyl­sulfonyl-1H-indol-3-yl]propan-1-one

M. Umadevi, V. Saravanan, R. Yamuna, A. K. Mohanakrishnan and G. Chakkaravarthi

Abstract top

In the title compound, C25H19ClN2O5S, the phenyl ring forms dihedral angles of 79.62 (12) and 80.02 (13)° with the indole ring system and the benzene ring, respectively. The nitro group is twisted at an angle of 22.39 (11)° with respect to the attached benzene ring. In the crystal, mol­ecules assemble into double layers in the ab plane via C-H...O inter­actions.

Introduction top

Experimental top

Synthesis and crystallization top

A solution of 1-(2-(bromo­methyl)-1-(phenyl­sulfonyl)-1H-indol-3-yl)propan-1-one (5 g, 12.31 mmol) and tri­phenyl­phosphine (3.5 g, 13.54 mmol) in dry THF (100 ml) was refluxed for 6 h. After consumption of the starting material, the solvent was removed under vacuum and the solid washed with di­ethyl ether to give the phospho­nium salt. Then, the mixture of phospho­nium salt (8 g, 11.97 mmol), 4-chloro-2-nitro­benzaldehyde (2.45 g, 13.17 mmol) and K2CO3 (3.30 g, 23.95 mmol) in DCM (70 ml) was stirred at room temperature for 24 h. After completion of the reaction (monitored by TLC), it was diluted using DCM (30 ml), washed with water (2 x 100 ml) and dried (Na2SO4). Removal of solvent in vacuo followed by trituration of the crude product with MeOH (20 ml) afforded the title compound.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were positioned geometrically and refined using riding model, with C—H = (0.93–0.97) Å and Uiso(H) = 1.2–1.5Ueq(C). Owing to poor agreement, the (001) reflection was omitted from the final cycles of refinement.

Results and discussion top

In continuation of our studies on indole derivatives which are known to exhibit anti-microbial, anti-biotic, analgesic and anti-cancer activities (Okabe and Adachi, 1998; Srivastava et al., 2011), we herewith report the crystal structure of the title compound (I). The geometric parameters of (I) (Fig. 1) are in close agreement with similar structures (Chakkaravarthi et al., 2008; 2010).

The phenyl ring makes the dihedral angle of 79.62 (12)° with the indole ring system. The phenyl ring (C1—C6) and the benzene ring (C20—C25) are inclined at an angle of 80.02 (13)°. The nitro group is twisted at an angle of 22.39 (11)° with respect to the attached benzene ring (C20—C25). The N1 atom is sp2 hybridised as the bond angles around N1 atom sum 352.4°. Details of the C—H···O inter­actions are given in Table 2 - these lead to layers in the ab plane.

Related literature top

For the biological activity of indole derivatives, see: Okabe & Adachi (1998); Srivastava et al. (2011). For related structures, see: Chakkaravarthi et al. (2008, 2010).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
(E)-1-[2-(4-Chloro-2-nitrostyryl)-1-phenylsulfonyl-1H-indol-3-yl]propan-1-one top
Crystal data top
C25H19ClN2O5SZ = 2
Mr = 494.93F(000) = 512
Triclinic, P1Dx = 1.422 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4658 (3) ÅCell parameters from 8917 reflections
b = 8.6643 (3) Åθ = 2.5–28.4°
c = 16.1126 (6) ŵ = 0.30 mm1
α = 84.196 (2)°T = 295 K
β = 87.768 (3)°Block, colourless
γ = 79.541 (2)°0.28 × 0.24 × 0.20 mm
V = 1156.01 (7) Å3
Data collection top
Bruker Kappa APEXII
diffractometer
6333 independent reflections
Radiation source: fine-focus sealed tube4536 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ω and φ scanθmax = 29.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.922, Tmax = 0.943k = 1111
25531 measured reflectionsl = 2022
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0709P)2 + 0.3517P]
where P = (Fo2 + 2Fc2)/3
6333 reflections(Δ/σ)max < 0.001
308 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
C25H19ClN2O5Sγ = 79.541 (2)°
Mr = 494.93V = 1156.01 (7) Å3
Triclinic, P1Z = 2
a = 8.4658 (3) ÅMo Kα radiation
b = 8.6643 (3) ŵ = 0.30 mm1
c = 16.1126 (6) ÅT = 295 K
α = 84.196 (2)°0.28 × 0.24 × 0.20 mm
β = 87.768 (3)°
Data collection top
Bruker Kappa APEXII
diffractometer
4536 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Rint = 0.029
Tmin = 0.922, Tmax = 0.943θmax = 29.5°
25531 measured reflectionsStandard reflections: 0
6333 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.150Δρmax = 0.49 e Å3
S = 1.03Δρmin = 0.39 e Å3
6333 reflectionsAbsolute structure: ?
308 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6620 (2)0.1560 (2)0.44142 (11)0.0497 (4)
C20.7468 (3)0.1501 (4)0.51342 (14)0.0765 (7)
H20.85700.11310.51400.092*
C30.6662 (4)0.1997 (5)0.58429 (16)0.0984 (11)
H30.72150.19450.63360.118*
C40.5062 (4)0.2564 (4)0.58242 (17)0.0920 (9)
H40.45370.29520.62980.110*
C50.4199 (4)0.2573 (4)0.51124 (19)0.0991 (10)
H50.30930.29230.51150.119*
C60.4985 (3)0.2060 (3)0.43989 (15)0.0781 (7)
H60.44200.20530.39160.094*
C70.6425 (2)0.3393 (2)0.23941 (10)0.0408 (4)
C80.6569 (2)0.4934 (2)0.22907 (10)0.0424 (4)
C90.7938 (2)0.5131 (2)0.27424 (11)0.0439 (4)
C100.8617 (3)0.6446 (2)0.28430 (14)0.0584 (5)
H100.81790.74350.25890.070*
C110.9950 (3)0.6244 (3)0.33266 (18)0.0738 (7)
H111.04050.71130.34120.089*
C121.0626 (3)0.4773 (3)0.36883 (18)0.0771 (7)
H121.15360.46750.40080.093*
C130.9999 (3)0.3449 (3)0.35916 (15)0.0625 (5)
H131.04660.24610.38360.075*
C140.8635 (2)0.3653 (2)0.31128 (11)0.0440 (4)
C150.5596 (2)0.6261 (2)0.17657 (12)0.0516 (5)
C160.5615 (3)0.6198 (3)0.08490 (12)0.0593 (5)
H16A0.50660.53590.07290.071*
H16B0.67220.59270.06570.071*
C170.4848 (4)0.7702 (3)0.03593 (16)0.0880 (8)
H17A0.37100.78840.04690.132*
H17B0.50530.76130.02260.132*
H17C0.52910.85660.05230.132*
C180.5229 (2)0.2611 (2)0.20724 (10)0.0442 (4)
H180.55630.16210.18840.053*
C190.3680 (2)0.3249 (2)0.20359 (11)0.0467 (4)
H190.33520.42500.22120.056*
C200.2462 (2)0.2449 (2)0.17303 (11)0.0453 (4)
C210.2582 (3)0.0828 (2)0.19095 (14)0.0566 (5)
H210.34660.02710.22010.068*
C220.1449 (3)0.0018 (2)0.16730 (14)0.0589 (5)
H220.15800.10700.17960.071*
C230.0107 (2)0.0832 (2)0.12499 (12)0.0518 (4)
C240.0071 (2)0.2427 (2)0.10536 (12)0.0487 (4)
H230.09630.29760.07640.058*
C250.1097 (2)0.3207 (2)0.12932 (11)0.0452 (4)
N10.77198 (17)0.25460 (17)0.28902 (9)0.0427 (3)
N30.0859 (2)0.4903 (2)0.10290 (11)0.0554 (4)
O10.6646 (2)0.00599 (16)0.31000 (9)0.0651 (4)
O20.92318 (19)0.02047 (18)0.37066 (10)0.0682 (4)
O30.4897 (3)0.7364 (2)0.20882 (12)0.1283 (11)
O50.04694 (18)0.55877 (18)0.08461 (11)0.0692 (4)
O60.2012 (2)0.5539 (2)0.09605 (17)0.1115 (9)
S10.76175 (6)0.08992 (5)0.35118 (3)0.04869 (14)
Cl10.13374 (7)0.01698 (7)0.09611 (4)0.07319 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0570 (11)0.0502 (10)0.0409 (9)0.0105 (8)0.0042 (8)0.0040 (7)
C20.0641 (14)0.121 (2)0.0511 (12)0.0321 (14)0.0066 (10)0.0076 (13)
C30.098 (2)0.169 (3)0.0489 (13)0.071 (2)0.0058 (13)0.0239 (17)
C40.114 (3)0.112 (2)0.0570 (15)0.0362 (19)0.0260 (16)0.0210 (15)
C50.0807 (18)0.127 (3)0.0700 (17)0.0174 (18)0.0207 (14)0.0128 (17)
C60.0669 (14)0.106 (2)0.0486 (12)0.0085 (14)0.0037 (10)0.0089 (12)
C70.0405 (8)0.0465 (9)0.0314 (7)0.0034 (7)0.0039 (6)0.0038 (6)
C80.0444 (9)0.0458 (9)0.0330 (8)0.0039 (7)0.0042 (7)0.0044 (7)
C90.0421 (9)0.0493 (9)0.0373 (8)0.0004 (7)0.0008 (7)0.0048 (7)
C100.0591 (12)0.0499 (11)0.0654 (13)0.0074 (9)0.0074 (10)0.0043 (9)
C110.0639 (14)0.0660 (14)0.0959 (18)0.0182 (11)0.0190 (13)0.0110 (13)
C120.0568 (13)0.0819 (17)0.0943 (19)0.0116 (12)0.0320 (13)0.0059 (14)
C130.0503 (11)0.0655 (13)0.0677 (13)0.0003 (9)0.0196 (10)0.0001 (10)
C140.0398 (8)0.0495 (9)0.0400 (9)0.0013 (7)0.0029 (7)0.0035 (7)
C150.0597 (11)0.0460 (10)0.0443 (10)0.0046 (8)0.0140 (8)0.0024 (8)
C160.0538 (11)0.0768 (14)0.0393 (9)0.0031 (10)0.0010 (8)0.0057 (9)
C170.117 (2)0.0850 (18)0.0532 (13)0.0059 (16)0.0168 (14)0.0213 (12)
C180.0476 (9)0.0459 (9)0.0369 (8)0.0009 (7)0.0060 (7)0.0045 (7)
C190.0471 (9)0.0481 (10)0.0424 (9)0.0022 (8)0.0022 (7)0.0042 (7)
C200.0412 (9)0.0489 (10)0.0430 (9)0.0024 (7)0.0006 (7)0.0014 (7)
C210.0533 (11)0.0505 (11)0.0612 (12)0.0003 (9)0.0098 (9)0.0045 (9)
C220.0625 (12)0.0478 (10)0.0644 (13)0.0080 (9)0.0033 (10)0.0017 (9)
C230.0503 (10)0.0574 (11)0.0486 (10)0.0131 (9)0.0045 (8)0.0052 (8)
C240.0388 (9)0.0563 (11)0.0482 (10)0.0044 (8)0.0006 (7)0.0001 (8)
C250.0395 (9)0.0479 (9)0.0447 (9)0.0028 (7)0.0035 (7)0.0015 (7)
N10.0420 (7)0.0436 (8)0.0389 (7)0.0004 (6)0.0064 (6)0.0001 (6)
N30.0441 (8)0.0534 (9)0.0655 (10)0.0064 (7)0.0053 (7)0.0068 (8)
O10.0916 (11)0.0455 (7)0.0589 (9)0.0115 (7)0.0143 (8)0.0052 (6)
O20.0624 (9)0.0575 (8)0.0722 (10)0.0174 (7)0.0096 (7)0.0063 (7)
O30.205 (3)0.0840 (13)0.0636 (11)0.0794 (16)0.0502 (14)0.0264 (10)
O50.0509 (8)0.0593 (9)0.0903 (12)0.0050 (7)0.0109 (8)0.0038 (8)
O60.0654 (11)0.0756 (12)0.189 (2)0.0286 (9)0.0420 (13)0.0514 (14)
S10.0554 (3)0.0407 (2)0.0451 (2)0.00326 (19)0.00822 (19)0.00039 (18)
Cl10.0676 (4)0.0741 (4)0.0840 (4)0.0276 (3)0.0047 (3)0.0088 (3)
Geometric parameters (Å, º) top
C1—C61.374 (3)C15—O31.185 (2)
C1—C21.380 (3)C15—C161.483 (3)
C1—S11.747 (2)C16—C171.506 (3)
C2—C31.373 (4)C16—H16A0.9700
C2—H20.9300C16—H16B0.9700
C3—C41.355 (5)C17—H17A0.9600
C3—H30.9300C17—H17B0.9600
C4—C51.383 (5)C17—H17C0.9600
C4—H40.9300C18—C191.329 (3)
C5—C61.378 (4)C18—H180.9300
C5—H50.9300C19—C201.468 (3)
C6—H60.9300C19—H190.9300
C7—C81.355 (3)C20—C211.391 (3)
C7—N11.427 (2)C20—C251.399 (2)
C7—C181.454 (2)C21—C221.373 (3)
C8—C91.437 (2)C21—H210.9300
C8—C151.493 (2)C22—C231.387 (3)
C9—C101.393 (3)C22—H220.9300
C9—C141.394 (2)C23—C241.369 (3)
C10—C111.371 (3)C23—Cl11.725 (2)
C10—H100.9300C24—C251.382 (3)
C11—C121.379 (4)C24—H230.9300
C11—H110.9300C25—N31.468 (2)
C12—C131.373 (3)N1—S11.6720 (15)
C12—H120.9300N3—O61.202 (2)
C13—C141.388 (3)N3—O51.205 (2)
C13—H130.9300O1—S11.4153 (16)
C14—N11.418 (2)O2—S11.4230 (15)
C6—C1—C2121.4 (2)C17—C16—H16A108.5
C6—C1—S1118.79 (16)C15—C16—H16B108.5
C2—C1—S1119.75 (18)C17—C16—H16B108.5
C3—C2—C1119.1 (3)H16A—C16—H16B107.5
C3—C2—H2120.5C16—C17—H17A109.5
C1—C2—H2120.5C16—C17—H17B109.5
C4—C3—C2120.0 (3)H17A—C17—H17B109.5
C4—C3—H3120.0C16—C17—H17C109.5
C2—C3—H3120.0H17A—C17—H17C109.5
C3—C4—C5121.1 (3)H17B—C17—H17C109.5
C3—C4—H4119.5C19—C18—C7122.80 (17)
C5—C4—H4119.5C19—C18—H18118.6
C6—C5—C4119.6 (3)C7—C18—H18118.6
C6—C5—H5120.2C18—C19—C20123.04 (17)
C4—C5—H5120.2C18—C19—H19118.5
C1—C6—C5118.7 (2)C20—C19—H19118.5
C1—C6—H6120.6C21—C20—C25115.37 (17)
C5—C6—H6120.6C21—C20—C19119.73 (16)
C8—C7—N1108.46 (15)C25—C20—C19124.82 (16)
C8—C7—C18129.63 (15)C22—C21—C20122.68 (18)
N1—C7—C18121.90 (15)C22—C21—H21118.7
C7—C8—C9108.69 (15)C20—C21—H21118.7
C7—C8—C15128.84 (16)C21—C22—C23119.55 (19)
C9—C8—C15122.37 (17)C21—C22—H22120.2
C10—C9—C14119.98 (17)C23—C22—H22120.2
C10—C9—C8132.32 (17)C24—C23—C22120.32 (19)
C14—C9—C8107.70 (16)C24—C23—Cl1119.70 (16)
C11—C10—C9118.2 (2)C22—C23—Cl1119.98 (16)
C11—C10—H10120.9C23—C24—C25118.76 (17)
C9—C10—H10120.9C23—C24—H23120.6
C10—C11—C12121.1 (2)C25—C24—H23120.6
C10—C11—H11119.5C24—C25—C20123.31 (17)
C12—C11—H11119.5C24—C25—N3115.63 (15)
C13—C12—C11122.2 (2)C20—C25—N3121.01 (16)
C13—C12—H12118.9C14—N1—C7107.57 (13)
C11—C12—H12118.9C14—N1—S1120.91 (11)
C12—C13—C14116.9 (2)C7—N1—S1123.89 (12)
C12—C13—H13121.5O6—N3—O5122.39 (18)
C14—C13—H13121.5O6—N3—C25118.61 (16)
C13—C14—C9121.65 (19)O5—N3—C25118.88 (16)
C13—C14—N1130.80 (18)O1—S1—O2120.22 (10)
C9—C14—N1107.55 (14)O1—S1—N1106.22 (8)
O3—C15—C16122.04 (18)O2—S1—N1106.01 (9)
O3—C15—C8119.14 (17)O1—S1—C1109.63 (10)
C16—C15—C8118.71 (16)O2—S1—C1109.04 (10)
C15—C16—C17114.9 (2)N1—S1—C1104.52 (8)
C15—C16—H16A108.5
C6—C1—C2—C31.9 (4)C25—C20—C21—C220.3 (3)
S1—C1—C2—C3178.8 (2)C19—C20—C21—C22177.18 (19)
C1—C2—C3—C41.3 (5)C20—C21—C22—C231.1 (3)
C2—C3—C4—C53.6 (5)C21—C22—C23—C241.4 (3)
C3—C4—C5—C62.7 (5)C21—C22—C23—Cl1179.18 (17)
C2—C1—C6—C52.7 (4)C22—C23—C24—C250.7 (3)
S1—C1—C6—C5179.7 (2)Cl1—C23—C24—C25179.79 (14)
C4—C5—C6—C10.4 (5)C23—C24—C25—C200.1 (3)
N1—C7—C8—C91.87 (19)C23—C24—C25—N3177.42 (17)
C18—C7—C8—C9179.19 (17)C21—C20—C25—C240.4 (3)
N1—C7—C8—C15174.39 (17)C19—C20—C25—C24176.37 (17)
C18—C7—C8—C154.6 (3)C21—C20—C25—N3177.05 (18)
C7—C8—C9—C10179.8 (2)C19—C20—C25—N36.2 (3)
C15—C8—C9—C103.2 (3)C13—C14—N1—C7179.4 (2)
C7—C8—C9—C140.9 (2)C9—C14—N1—C71.50 (18)
C15—C8—C9—C14175.62 (16)C13—C14—N1—S128.8 (3)
C14—C9—C10—C111.5 (3)C9—C14—N1—S1152.11 (13)
C8—C9—C10—C11179.8 (2)C8—C7—N1—C142.11 (19)
C9—C10—C11—C121.6 (4)C18—C7—N1—C14178.85 (15)
C10—C11—C12—C130.7 (4)C8—C7—N1—S1151.63 (13)
C11—C12—C13—C140.3 (4)C18—C7—N1—S129.3 (2)
C12—C13—C14—C90.4 (3)C24—C25—N3—O6155.4 (2)
C12—C13—C14—N1179.3 (2)C20—C25—N3—O622.2 (3)
C10—C9—C14—C130.5 (3)C24—C25—N3—O520.7 (3)
C8—C9—C14—C13179.57 (18)C20—C25—N3—O5161.72 (19)
C10—C9—C14—N1178.64 (17)C14—N1—S1—O1178.89 (13)
C8—C9—C14—N10.39 (19)C7—N1—S1—O135.43 (16)
C7—C8—C15—O3121.1 (3)C14—N1—S1—O249.93 (15)
C9—C8—C15—O363.1 (3)C7—N1—S1—O2164.38 (14)
C7—C8—C15—C1662.5 (3)C14—N1—S1—C165.22 (15)
C9—C8—C15—C16113.3 (2)C7—N1—S1—C180.47 (15)
O3—C15—C16—C176.7 (4)C6—C1—S1—O137.0 (2)
C8—C15—C16—C17169.6 (2)C2—C1—S1—O1139.98 (19)
C8—C7—C18—C1939.8 (3)C6—C1—S1—O2170.50 (19)
N1—C7—C18—C19141.39 (18)C2—C1—S1—O26.5 (2)
C7—C18—C19—C20178.51 (16)C6—C1—S1—N176.5 (2)
C18—C19—C20—C2137.1 (3)C2—C1—S1—N1106.5 (2)
C18—C19—C20—C25146.33 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O1i0.932.603.327 (3)136
C16—H16B···O5ii0.972.373.260 (3)152
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O1i0.932.603.327 (3)136
C16—H16B···O5ii0.972.373.260 (3)152
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.
Acknowledgements top

The authors wish to acknowledge the SAIF, IIT Madras, for the data collection.

references
References top

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