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

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

doi:10.1107/S1600536813031073

organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1784

doi:10.1107/S1600536813031073

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

M. Umadevi,^a V. Saravanan,^b R. Yamuna,^c ^* A. K. Mohanakrishnan ^b and G. Chakkaravarthi ^d ^*

^aResearch Scholar (Chemistry), Bharathiyar University, Coimbatore 641 046, Tamilnadu, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Sciences, Chemistry and Materials Research Lab, Amrita Vishwa Vidyapeetham University, Ettimadai, Coimbatore 641 112, India, and ^dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: ryamuna1@gmail.com, chakkaravarthi_2005@yahoo.com

(Received 8 November 2013; accepted 12 November 2013; online 16 November 2013)

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.

CCDC reference: 971553

Related literature

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

Experimental

Crystal data

C₂₅H₁₉ClN₂O₅S
M_r = 494.93
Triclinic, $[P \overline 1]$
a = 8.4658 (3) Å
b = 8.6643 (3) Å
c = 16.1126 (6) Å
α = 84.196 (2)°
β = 87.768 (3)°
γ = 79.541 (2)°
V = 1156.01 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.922, T_max = 0.943
25531 measured reflections
6333 independent reflections
4536 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.150
S = 1.03
6333 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O1ⁱ	0.93	2.60	3.327 (3)	136
C16—H16B⋯O5ⁱⁱ	0.97	2.37	3.260 (3)	152
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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.

Supporting information

CCDC reference: 971553

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813031073/tk5271sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031073/tk5271Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813031073/tk5271Isup3.cml

checkCIF report

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 U_iso(H) = 1.2–1.5U_eq(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

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

C₂₅H₁₉ClN₂O₅S	Z = 2
M_r = 494.93	F(000) = 512
Triclinic, P1	D_x = 1.422 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4658 (3) Å	Cell parameters from 8917 reflections
b = 8.6643 (3) Å	θ = 2.5–28.4°
c = 16.1126 (6) Å	µ = 0.30 mm⁻¹
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 tube	4536 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and ϕ scan	θ_max = 29.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.922, T_max = 0.943	k = −11→11
25531 measured reflections	l = −20→22

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0709P)² + 0.3517P] where P = (F_o² + 2F_c²)/3
6333 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₅H₁₉ClN₂O₅S	γ = 79.541 (2)°
M_r = 494.93	V = 1156.01 (7) Å³
Triclinic, P1	Z = 2
a = 8.4658 (3) Å	Mo Kα radiation
b = 8.6643 (3) Å	µ = 0.30 mm⁻¹
c = 16.1126 (6) Å	T = 295 K
α = 84.196 (2)°	0.28 × 0.24 × 0.20 mm
β = 87.768 (3)°

Data collection top

Bruker Kappa APEXII diffractometer	6333 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4536 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.943	R_int = 0.029
25531 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.03	Δρ_max = 0.49 e Å⁻³
6333 reflections	Δρ_min = −0.39 e Å⁻³
308 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6620 (2)	0.1560 (2)	0.44142 (11)	0.0497 (4)
C2	0.7468 (3)	0.1501 (4)	0.51342 (14)	0.0765 (7)
H2	0.8570	0.1131	0.5140	0.092*
C3	0.6662 (4)	0.1997 (5)	0.58429 (16)	0.0984 (11)
H3	0.7215	0.1945	0.6336	0.118*
C4	0.5062 (4)	0.2564 (4)	0.58242 (17)	0.0920 (9)
H4	0.4537	0.2952	0.6298	0.110*
C5	0.4199 (4)	0.2573 (4)	0.51124 (19)	0.0991 (10)
H5	0.3093	0.2923	0.5115	0.119*
C6	0.4985 (3)	0.2060 (3)	0.43989 (15)	0.0781 (7)
H6	0.4420	0.2053	0.3916	0.094*
C7	0.6425 (2)	0.3393 (2)	0.23941 (10)	0.0408 (4)
C8	0.6569 (2)	0.4934 (2)	0.22907 (10)	0.0424 (4)
C9	0.7938 (2)	0.5131 (2)	0.27424 (11)	0.0439 (4)
C10	0.8617 (3)	0.6446 (2)	0.28430 (14)	0.0584 (5)
H10	0.8179	0.7435	0.2589	0.070*
C11	0.9950 (3)	0.6244 (3)	0.33266 (18)	0.0738 (7)
H11	1.0405	0.7113	0.3412	0.089*
C12	1.0626 (3)	0.4773 (3)	0.36883 (18)	0.0771 (7)
H12	1.1536	0.4675	0.4008	0.093*
C13	0.9999 (3)	0.3449 (3)	0.35916 (15)	0.0625 (5)
H13	1.0466	0.2461	0.3836	0.075*
C14	0.8635 (2)	0.3653 (2)	0.31128 (11)	0.0440 (4)
C15	0.5596 (2)	0.6261 (2)	0.17657 (12)	0.0516 (5)
C16	0.5615 (3)	0.6198 (3)	0.08490 (12)	0.0593 (5)
H16A	0.5066	0.5359	0.0729	0.071*
H16B	0.6722	0.5927	0.0657	0.071*
C17	0.4848 (4)	0.7702 (3)	0.03593 (16)	0.0880 (8)
H17A	0.3710	0.7884	0.0469	0.132*
H17B	0.5053	0.7613	−0.0226	0.132*
H17C	0.5291	0.8566	0.0523	0.132*
C18	0.5229 (2)	0.2611 (2)	0.20724 (10)	0.0442 (4)
H18	0.5563	0.1621	0.1884	0.053*
C19	0.3680 (2)	0.3249 (2)	0.20359 (11)	0.0467 (4)
H19	0.3352	0.4250	0.2212	0.056*
C20	0.2462 (2)	0.2449 (2)	0.17303 (11)	0.0453 (4)
C21	0.2582 (3)	0.0828 (2)	0.19095 (14)	0.0566 (5)
H21	0.3466	0.0271	0.2201	0.068*
C22	0.1449 (3)	0.0018 (2)	0.16730 (14)	0.0589 (5)
H22	0.1580	−0.1070	0.1796	0.071*
C23	0.0107 (2)	0.0832 (2)	0.12499 (12)	0.0518 (4)
C24	−0.0071 (2)	0.2427 (2)	0.10536 (12)	0.0487 (4)
H23	−0.0963	0.2976	0.0764	0.058*
C25	0.1097 (2)	0.3207 (2)	0.12932 (11)	0.0452 (4)
N1	0.77198 (17)	0.25460 (17)	0.28902 (9)	0.0427 (3)
N3	0.0859 (2)	0.4903 (2)	0.10290 (11)	0.0554 (4)
O1	0.6646 (2)	0.00599 (16)	0.31000 (9)	0.0651 (4)
O2	0.92318 (19)	0.02047 (18)	0.37066 (10)	0.0682 (4)
O3	0.4897 (3)	0.7364 (2)	0.20882 (12)	0.1283 (11)
O5	−0.04694 (18)	0.55877 (18)	0.08461 (11)	0.0692 (4)
O6	0.2012 (2)	0.5539 (2)	0.09605 (17)	0.1115 (9)
S1	0.76175 (6)	0.08992 (5)	0.35118 (3)	0.04869 (14)
Cl1	−0.13374 (7)	−0.01698 (7)	0.09611 (4)	0.07319 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0570 (11)	0.0502 (10)	0.0409 (9)	−0.0105 (8)	−0.0042 (8)	0.0040 (7)
C2	0.0641 (14)	0.121 (2)	0.0511 (12)	−0.0321 (14)	−0.0066 (10)	−0.0076 (13)
C3	0.098 (2)	0.169 (3)	0.0489 (13)	−0.071 (2)	0.0058 (13)	−0.0239 (17)
C4	0.114 (3)	0.112 (2)	0.0570 (15)	−0.0362 (19)	0.0260 (16)	−0.0210 (15)
C5	0.0807 (18)	0.127 (3)	0.0700 (17)	0.0174 (18)	0.0207 (14)	0.0128 (17)
C6	0.0669 (14)	0.106 (2)	0.0486 (12)	0.0085 (14)	−0.0037 (10)	0.0089 (12)
C7	0.0405 (8)	0.0465 (9)	0.0314 (7)	0.0034 (7)	−0.0039 (6)	−0.0038 (6)
C8	0.0444 (9)	0.0458 (9)	0.0330 (8)	0.0039 (7)	−0.0042 (7)	−0.0044 (7)
C9	0.0421 (9)	0.0493 (9)	0.0373 (8)	−0.0004 (7)	−0.0008 (7)	−0.0048 (7)
C10	0.0591 (12)	0.0499 (11)	0.0654 (13)	−0.0074 (9)	−0.0074 (10)	−0.0043 (9)
C11	0.0639 (14)	0.0660 (14)	0.0959 (18)	−0.0182 (11)	−0.0190 (13)	−0.0110 (13)
C12	0.0568 (13)	0.0819 (17)	0.0943 (19)	−0.0116 (12)	−0.0320 (13)	−0.0059 (14)
C13	0.0503 (11)	0.0655 (13)	0.0677 (13)	0.0003 (9)	−0.0196 (10)	0.0001 (10)
C14	0.0398 (8)	0.0495 (9)	0.0400 (9)	−0.0013 (7)	−0.0029 (7)	−0.0035 (7)
C15	0.0597 (11)	0.0460 (10)	0.0443 (10)	0.0046 (8)	−0.0140 (8)	−0.0024 (8)
C16	0.0538 (11)	0.0768 (14)	0.0393 (9)	0.0031 (10)	−0.0010 (8)	0.0057 (9)
C17	0.117 (2)	0.0850 (18)	0.0532 (13)	−0.0059 (16)	−0.0168 (14)	0.0213 (12)
C18	0.0476 (9)	0.0459 (9)	0.0369 (8)	−0.0009 (7)	−0.0060 (7)	−0.0045 (7)
C19	0.0471 (9)	0.0481 (10)	0.0424 (9)	−0.0022 (8)	−0.0022 (7)	−0.0042 (7)
C20	0.0412 (9)	0.0489 (10)	0.0430 (9)	−0.0024 (7)	0.0006 (7)	−0.0014 (7)
C21	0.0533 (11)	0.0505 (11)	0.0612 (12)	−0.0003 (9)	−0.0098 (9)	0.0045 (9)
C22	0.0625 (12)	0.0478 (10)	0.0644 (13)	−0.0080 (9)	−0.0033 (10)	0.0017 (9)
C23	0.0503 (10)	0.0574 (11)	0.0486 (10)	−0.0131 (9)	0.0045 (8)	−0.0052 (8)
C24	0.0388 (9)	0.0563 (11)	0.0482 (10)	−0.0044 (8)	0.0006 (7)	−0.0001 (8)
C25	0.0395 (9)	0.0479 (9)	0.0447 (9)	−0.0028 (7)	0.0035 (7)	0.0015 (7)
N1	0.0420 (7)	0.0436 (8)	0.0389 (7)	0.0004 (6)	−0.0064 (6)	0.0001 (6)
N3	0.0441 (8)	0.0534 (9)	0.0655 (10)	−0.0064 (7)	−0.0053 (7)	0.0068 (8)
O1	0.0916 (11)	0.0455 (7)	0.0589 (9)	−0.0115 (7)	−0.0143 (8)	−0.0052 (6)
O2	0.0624 (9)	0.0575 (8)	0.0722 (10)	0.0174 (7)	−0.0096 (7)	0.0063 (7)
O3	0.205 (3)	0.0840 (13)	0.0636 (11)	0.0794 (16)	−0.0502 (14)	−0.0264 (10)
O5	0.0509 (8)	0.0593 (9)	0.0903 (12)	0.0050 (7)	−0.0109 (8)	0.0038 (8)
O6	0.0654 (11)	0.0756 (12)	0.189 (2)	−0.0286 (9)	−0.0420 (13)	0.0514 (14)
S1	0.0554 (3)	0.0407 (2)	0.0451 (2)	0.00326 (19)	−0.00822 (19)	0.00039 (18)
Cl1	0.0676 (4)	0.0741 (4)	0.0840 (4)	−0.0276 (3)	−0.0047 (3)	−0.0088 (3)

Geometric parameters (Å, º) top

C1—C6	1.374 (3)	C15—O3	1.185 (2)
C1—C2	1.380 (3)	C15—C16	1.483 (3)
C1—S1	1.747 (2)	C16—C17	1.506 (3)
C2—C3	1.373 (4)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.355 (5)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.383 (5)	C17—H17C	0.9600
C4—H4	0.9300	C18—C19	1.329 (3)
C5—C6	1.378 (4)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.468 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.355 (3)	C20—C21	1.391 (3)
C7—N1	1.427 (2)	C20—C25	1.399 (2)
C7—C18	1.454 (2)	C21—C22	1.373 (3)
C8—C9	1.437 (2)	C21—H21	0.9300
C8—C15	1.493 (2)	C22—C23	1.387 (3)
C9—C10	1.393 (3)	C22—H22	0.9300
C9—C14	1.394 (2)	C23—C24	1.369 (3)
C10—C11	1.371 (3)	C23—Cl1	1.725 (2)
C10—H10	0.9300	C24—C25	1.382 (3)
C11—C12	1.379 (4)	C24—H23	0.9300
C11—H11	0.9300	C25—N3	1.468 (2)
C12—C13	1.373 (3)	N1—S1	1.6720 (15)
C12—H12	0.9300	N3—O6	1.202 (2)
C13—C14	1.388 (3)	N3—O5	1.205 (2)
C13—H13	0.9300	O1—S1	1.4153 (16)
C14—N1	1.418 (2)	O2—S1	1.4230 (15)

C6—C1—C2	121.4 (2)	C17—C16—H16A	108.5
C6—C1—S1	118.79 (16)	C15—C16—H16B	108.5
C2—C1—S1	119.75 (18)	C17—C16—H16B	108.5
C3—C2—C1	119.1 (3)	H16A—C16—H16B	107.5
C3—C2—H2	120.5	C16—C17—H17A	109.5
C1—C2—H2	120.5	C16—C17—H17B	109.5
C4—C3—C2	120.0 (3)	H17A—C17—H17B	109.5
C4—C3—H3	120.0	C16—C17—H17C	109.5
C2—C3—H3	120.0	H17A—C17—H17C	109.5
C3—C4—C5	121.1 (3)	H17B—C17—H17C	109.5
C3—C4—H4	119.5	C19—C18—C7	122.80 (17)
C5—C4—H4	119.5	C19—C18—H18	118.6
C6—C5—C4	119.6 (3)	C7—C18—H18	118.6
C6—C5—H5	120.2	C18—C19—C20	123.04 (17)
C4—C5—H5	120.2	C18—C19—H19	118.5
C1—C6—C5	118.7 (2)	C20—C19—H19	118.5
C1—C6—H6	120.6	C21—C20—C25	115.37 (17)
C5—C6—H6	120.6	C21—C20—C19	119.73 (16)
C8—C7—N1	108.46 (15)	C25—C20—C19	124.82 (16)
C8—C7—C18	129.63 (15)	C22—C21—C20	122.68 (18)
N1—C7—C18	121.90 (15)	C22—C21—H21	118.7
C7—C8—C9	108.69 (15)	C20—C21—H21	118.7
C7—C8—C15	128.84 (16)	C21—C22—C23	119.55 (19)
C9—C8—C15	122.37 (17)	C21—C22—H22	120.2
C10—C9—C14	119.98 (17)	C23—C22—H22	120.2
C10—C9—C8	132.32 (17)	C24—C23—C22	120.32 (19)
C14—C9—C8	107.70 (16)	C24—C23—Cl1	119.70 (16)
C11—C10—C9	118.2 (2)	C22—C23—Cl1	119.98 (16)
C11—C10—H10	120.9	C23—C24—C25	118.76 (17)
C9—C10—H10	120.9	C23—C24—H23	120.6
C10—C11—C12	121.1 (2)	C25—C24—H23	120.6
C10—C11—H11	119.5	C24—C25—C20	123.31 (17)
C12—C11—H11	119.5	C24—C25—N3	115.63 (15)
C13—C12—C11	122.2 (2)	C20—C25—N3	121.01 (16)
C13—C12—H12	118.9	C14—N1—C7	107.57 (13)
C11—C12—H12	118.9	C14—N1—S1	120.91 (11)
C12—C13—C14	116.9 (2)	C7—N1—S1	123.89 (12)
C12—C13—H13	121.5	O6—N3—O5	122.39 (18)
C14—C13—H13	121.5	O6—N3—C25	118.61 (16)
C13—C14—C9	121.65 (19)	O5—N3—C25	118.88 (16)
C13—C14—N1	130.80 (18)	O1—S1—O2	120.22 (10)
C9—C14—N1	107.55 (14)	O1—S1—N1	106.22 (8)
O3—C15—C16	122.04 (18)	O2—S1—N1	106.01 (9)
O3—C15—C8	119.14 (17)	O1—S1—C1	109.63 (10)
C16—C15—C8	118.71 (16)	O2—S1—C1	109.04 (10)
C15—C16—C17	114.9 (2)	N1—S1—C1	104.52 (8)
C15—C16—H16A	108.5

C6—C1—C2—C3	−1.9 (4)	C25—C20—C21—C22	0.3 (3)
S1—C1—C2—C3	−178.8 (2)	C19—C20—C21—C22	177.18 (19)
C1—C2—C3—C4	−1.3 (5)	C20—C21—C22—C23	−1.1 (3)
C2—C3—C4—C5	3.6 (5)	C21—C22—C23—C24	1.4 (3)
C3—C4—C5—C6	−2.7 (5)	C21—C22—C23—Cl1	−179.18 (17)
C2—C1—C6—C5	2.7 (4)	C22—C23—C24—C25	−0.7 (3)
S1—C1—C6—C5	179.7 (2)	Cl1—C23—C24—C25	179.79 (14)
C4—C5—C6—C1	−0.4 (5)	C23—C24—C25—C20	−0.1 (3)
N1—C7—C8—C9	−1.87 (19)	C23—C24—C25—N3	177.42 (17)
C18—C7—C8—C9	179.19 (17)	C21—C20—C25—C24	0.4 (3)
N1—C7—C8—C15	174.39 (17)	C19—C20—C25—C24	−176.37 (17)
C18—C7—C8—C15	−4.6 (3)	C21—C20—C25—N3	−177.05 (18)
C7—C8—C9—C10	179.8 (2)	C19—C20—C25—N3	6.2 (3)
C15—C8—C9—C10	3.2 (3)	C13—C14—N1—C7	179.4 (2)
C7—C8—C9—C14	0.9 (2)	C9—C14—N1—C7	−1.50 (18)
C15—C8—C9—C14	−175.62 (16)	C13—C14—N1—S1	28.8 (3)
C14—C9—C10—C11	−1.5 (3)	C9—C14—N1—S1	−152.11 (13)
C8—C9—C10—C11	179.8 (2)	C8—C7—N1—C14	2.11 (19)
C9—C10—C11—C12	1.6 (4)	C18—C7—N1—C14	−178.85 (15)
C10—C11—C12—C13	−0.7 (4)	C8—C7—N1—S1	151.63 (13)
C11—C12—C13—C14	−0.3 (4)	C18—C7—N1—S1	−29.3 (2)
C12—C13—C14—C9	0.4 (3)	C24—C25—N3—O6	−155.4 (2)
C12—C13—C14—N1	179.3 (2)	C20—C25—N3—O6	22.2 (3)
C10—C9—C14—C13	0.5 (3)	C24—C25—N3—O5	20.7 (3)
C8—C9—C14—C13	179.57 (18)	C20—C25—N3—O5	−161.72 (19)
C10—C9—C14—N1	−178.64 (17)	C14—N1—S1—O1	−178.89 (13)
C8—C9—C14—N1	0.39 (19)	C7—N1—S1—O1	35.43 (16)
C7—C8—C15—O3	121.1 (3)	C14—N1—S1—O2	−49.93 (15)
C9—C8—C15—O3	−63.1 (3)	C7—N1—S1—O2	164.38 (14)
C7—C8—C15—C16	−62.5 (3)	C14—N1—S1—C1	65.22 (15)
C9—C8—C15—C16	113.3 (2)	C7—N1—S1—C1	−80.47 (15)
O3—C15—C16—C17	6.7 (4)	C6—C1—S1—O1	−37.0 (2)
C8—C15—C16—C17	−169.6 (2)	C2—C1—S1—O1	139.98 (19)
C8—C7—C18—C19	−39.8 (3)	C6—C1—S1—O2	−170.50 (19)
N1—C7—C18—C19	141.39 (18)	C2—C1—S1—O2	6.5 (2)
C7—C18—C19—C20	−178.51 (16)	C6—C1—S1—N1	76.5 (2)
C18—C19—C20—C21	37.1 (3)	C2—C1—S1—N1	−106.5 (2)
C18—C19—C20—C25	−146.33 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱ	0.93	2.60	3.327 (3)	136
C16—H16B···O5ⁱⁱ	0.97	2.37	3.260 (3)	152

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱ	0.93	2.60	3.327 (3)	136
C16—H16B···O5ⁱⁱ	0.97	2.37	3.260 (3)	152

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Acknowledgements

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

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o749. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chakkaravarthi, G., Panchatcharam, R., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2010). Acta Cryst. E66, o2957. Web of Science CSD CrossRef IUCr Journals Google Scholar
Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386–387. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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(E)-1-[2-(4-Chloro-2-nitro­styr­yl)-1-phenyl­sulfonyl-1H-indol-3-yl]propan-1-one

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