Ethyl 1-benzene­sulfonyl-2-[(E)-2-(2-methyl­phen­yl)ethen­yl]indole-3-carboxyl­ate

Ramathilagam, C.; Saravanan, V.; Mohanakrishnan, A.K.; Chakkaravarthi, G.; Umarani, P.R.; Manivannan, V.

doi:10.1107/S1600536811001863

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o448

doi:10.1107/S1600536811001863

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Ethyl 1-benzenesulfonyl-2-[(E)-2-(2-methylphenyl)ethenyl]indole-3-carboxylate

C. Ramathilagam,^a V. Saravanan,^b A. K. Mohanakrishnan,^b G. Chakkaravarthi,^c P. R. Umarani ^d and V. Manivannan ^e ^*

^aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^dDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: crystallography2010@gmail.com

(Received 2 January 2011; accepted 12 January 2011; online 22 January 2011)

In the title compound, C₂₆H₂₃NO₄S, the phenyl, tolyl and ester groups make dihedral angles of 82.28 (5), 77.67 (6) and 8.52 (6)°, respectively, with the indole ring system. The S atom of the sulfonyl group is displaced by 0.1968 (4) Å from the indole mean plane. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions. The crystal structure structure features short intramolecular C—H⋯O contacts and π–π stacking interactions between the phenyl and tolyl groups [centroid–centroid distance = 3.9448 (11) Å].

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001 ); Kolocouris et al. (1994 ); Merck (1973 ). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007 , 2008 ).

Experimental

Crystal data

C₂₆H₂₃NO₄S
M_r = 445.51
Monoclinic, P 2₁ /n
a = 10.4248 (4) Å
b = 8.3629 (3) Å
c = 25.2284 (11) Å
β = 92.902 (1)°
V = 2196.63 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 295 K
0.24 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.958, T_max = 0.968
22952 measured reflections
4848 independent reflections
3551 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.117
S = 1.03
4848 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O3	0.93	2.48	3.000 (3)	116
C13—H13⋯O1	0.93	2.33	2.908 (3)	120
C16—H16A⋯O1ⁱ	0.97	2.56	3.381 (3)	143
Symmetry code: (i) 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001863/gk2338sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001863/gk2338Isup2.hkl

checkCIF report

Comment top

Indole derivatives exhibit antihypertensive (Merck, 1973), antitumour (Andreani et al., 2001) and antiviral (Kolocouris et al., 1994) activities. The geometric parameters of the title molecule (Fig. 1) agree well with the reported similar structures (Chakkaravarthi et al. 2007, 2008).

The phenyl ring makes the dihedral angle of 82.28 (5)° with the indole ring system. The benzene ring (C20—C25) forms the dihedral angle of 77.67 (6)° with the indole ring system. The S atom of the sulfonyl group is displaced 0.1968 (4)Å from the indole mean plane. The sum of the bond angles around N1 [358.5 (1)°] indicates that N1 atom is sp² hybridized. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing exhibits weak intermolecular C—H···O (Fig.2 and Table 1) and π–π interactions [Cg2···Cg4 (1/2 - x,-1/2 + y,1/2 - z) distance of 3.9448 (11) Å; Cg2 and Cg4 are the centroids of C1—C6 ring and C20—C26 ring, respectively] .

Related literature top

For the biological activity of indole derivatives, see: Andreani et al. (2001); Kolocouris et al. (1994); Merck (1973). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007, 2008).

Experimental top

To a suspension of hexane (5 ml) washed NaH (0.29 g, 6.10 mmol) in dry THF (10 ml) at -10° C under N₂ atmosphere was slowly added the solution of diethyl (3-(ethoxycarbonyl)-1-phenylsulfonyl-1H-indol-2-yl)methylphosphonate (0.97 g, 2.03 mmol) in dry THF (5 ml) via syringe and stirred for 15 min. Then a solution of 2-methylbenzaldehyde (0.28 g, 2.32 mmol) in dry THF (5 ml) was added and allowed to stir for additional 2 h. After completion of the product formation (monitored by TLC), it was then poured over crushed ice (100 g) containing conc. HCl (3 ml). The solid formed was filtered and recrystalized with MeOH to afford ethyl 2-(2-methylstyryl)-1-phenylsulfonyl -1H-indole-3-carboxylate as bright yellow crystals [0.70 g, 78%; melting point 371–373 K].

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 the title compound with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal packing viewed down the b axis. Intermolecular C-H···O interactionshydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Ethyl 1-benzenesulfonyl-2-[(E)-2-(2-methylphenyl)ethenyl]indole-3-carboxylate top

Crystal data top

C₂₆H₂₃NO₄S	F(000) = 936
M_r = 445.51	D_x = 1.347 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 31039 reflections
a = 10.4248 (4) Å	θ = 2.1–31.4°
b = 8.3629 (3) Å	µ = 0.18 mm⁻¹
c = 25.2284 (11) Å	T = 295 K
β = 92.902 (1)°	Block, yellow
V = 2196.63 (15) Å³	0.24 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4848 independent reflections
Radiation source: fine-focus sealed tube	3551 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and ϕ scans	θ_max = 27.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
T_min = 0.958, T_max = 0.968	k = −10→10
22952 measured reflections	l = −32→32

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0499P)² + 0.6907P] where P = (F_o² + 2F_c²)/3
4848 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₆H₂₃NO₄S	V = 2196.63 (15) Å³
M_r = 445.51	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.4248 (4) Å	µ = 0.18 mm⁻¹
b = 8.3629 (3) Å	T = 295 K
c = 25.2284 (11) Å	0.24 × 0.20 × 0.18 mm
β = 92.902 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	4848 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3551 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.968	R_int = 0.029
22952 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
4848 reflections	Δρ_min = −0.28 e Å⁻³
291 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.29596 (16)	0.5477 (2)	0.13482 (7)	0.0434 (4)
C2	0.33149 (19)	0.4055 (2)	0.11194 (7)	0.0516 (4)
H2	0.3705	0.4051	0.0796	0.062*
C3	0.3082 (2)	0.2640 (2)	0.13788 (8)	0.0563 (5)
H3	0.3314	0.1672	0.1229	0.068*
C4	0.2511 (2)	0.2656 (2)	0.18551 (8)	0.0582 (5)
H4	0.2353	0.1697	0.2027	0.070*
C5	0.2170 (2)	0.4074 (3)	0.20820 (8)	0.0641 (6)
H5	0.1793	0.4073	0.2408	0.077*
C6	0.23856 (19)	0.5502 (2)	0.18277 (8)	0.0549 (5)
H6	0.2147	0.6466	0.1978	0.066*
C7	0.07971 (18)	0.81521 (19)	0.06872 (6)	0.0439 (4)
C8	−0.00146 (19)	0.7883 (2)	0.02544 (6)	0.0466 (4)
C9	0.0676 (2)	0.7013 (2)	−0.01332 (7)	0.0505 (5)
C10	0.0332 (2)	0.6438 (2)	−0.06437 (7)	0.0644 (6)
H10	−0.0487	0.6611	−0.0796	0.077*
C11	0.1231 (3)	0.5617 (3)	−0.09121 (9)	0.0782 (8)
H11	0.1019	0.5246	−0.1253	0.094*
C12	0.2444 (3)	0.5327 (3)	−0.06897 (9)	0.0803 (8)
H12	0.3020	0.4733	−0.0879	0.096*
C13	0.2824 (3)	0.5898 (3)	−0.01920 (8)	0.0698 (6)
H13	0.3647	0.5719	−0.0045	0.084*
C14	0.1920 (2)	0.6752 (2)	0.00782 (7)	0.0530 (5)
C15	−0.1351 (2)	0.8425 (2)	0.01525 (7)	0.0520 (5)
C16	−0.3192 (2)	0.9600 (3)	0.04901 (9)	0.0683 (6)
H16A	−0.3749	0.8700	0.0401	0.082*
H16B	−0.3273	1.0375	0.0204	0.082*
C17	−0.3556 (3)	1.0338 (3)	0.09964 (11)	0.0900 (8)
H17A	−0.2996	1.1223	0.1081	0.135*
H17B	−0.3479	0.9558	0.1275	0.135*
H17C	−0.4427	1.0710	0.0960	0.135*
C18	0.05757 (17)	0.9015 (2)	0.11824 (6)	0.0458 (4)
H18	0.1021	0.9965	0.1247	0.055*
C19	−0.02112 (18)	0.8527 (2)	0.15390 (6)	0.0479 (4)
H19	−0.0617	0.7549	0.1479	0.057*
C20	−0.05081 (16)	0.9393 (2)	0.20259 (7)	0.0445 (4)
C21	−0.07577 (16)	0.8570 (2)	0.24966 (6)	0.0460 (4)
C22	−0.10097 (19)	0.9451 (3)	0.29430 (7)	0.0570 (5)
H22	−0.1176	0.8917	0.3255	0.068*
C23	−0.1022 (2)	1.1089 (3)	0.29386 (8)	0.0644 (6)
H23	−0.1181	1.1652	0.3246	0.077*
C24	−0.0800 (2)	1.1895 (3)	0.24804 (9)	0.0644 (6)
H24	−0.0816	1.3007	0.2475	0.077*
C25	−0.05529 (19)	1.1053 (2)	0.20262 (8)	0.0543 (5)
H25	−0.0414	1.1607	0.1715	0.065*
C26	−0.0706 (2)	0.6777 (2)	0.25305 (8)	0.0594 (5)
H26A	−0.0929	0.6442	0.2878	0.089*
H26B	0.0146	0.6417	0.2465	0.089*
H26C	−0.1304	0.6326	0.2270	0.089*
N1	0.20131 (15)	0.75147 (17)	0.05839 (6)	0.0494 (4)
O1	0.43527 (14)	0.70935 (19)	0.07195 (6)	0.0717 (4)
O2	0.31983 (13)	0.85612 (15)	0.13962 (5)	0.0603 (4)
O3	−0.19140 (16)	0.8300 (2)	−0.02733 (6)	0.0866 (5)
O4	−0.18768 (13)	0.90745 (18)	0.05650 (5)	0.0618 (4)
S1	0.32570 (5)	0.72867 (5)	0.10266 (2)	0.05081 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0433 (9)	0.0401 (8)	0.0464 (9)	−0.0039 (7)	−0.0009 (7)	0.0010 (7)
C2	0.0587 (12)	0.0467 (10)	0.0492 (10)	0.0004 (8)	0.0014 (9)	−0.0044 (8)
C3	0.0654 (13)	0.0397 (9)	0.0624 (12)	0.0005 (9)	−0.0099 (10)	−0.0035 (8)
C4	0.0644 (13)	0.0464 (10)	0.0625 (12)	−0.0059 (9)	−0.0087 (10)	0.0116 (9)
C5	0.0771 (15)	0.0591 (12)	0.0571 (12)	−0.0003 (11)	0.0132 (10)	0.0104 (10)
C6	0.0661 (12)	0.0454 (10)	0.0538 (11)	0.0034 (9)	0.0104 (9)	0.0007 (8)
C7	0.0591 (11)	0.0362 (8)	0.0371 (8)	−0.0067 (8)	0.0108 (8)	0.0032 (7)
C8	0.0653 (12)	0.0390 (9)	0.0363 (9)	−0.0110 (8)	0.0094 (8)	0.0019 (7)
C9	0.0780 (14)	0.0366 (9)	0.0380 (9)	−0.0125 (9)	0.0134 (9)	0.0027 (7)
C10	0.1043 (17)	0.0483 (11)	0.0412 (10)	−0.0157 (11)	0.0112 (10)	−0.0031 (9)
C11	0.146 (3)	0.0495 (12)	0.0414 (11)	−0.0110 (14)	0.0231 (14)	−0.0058 (9)
C12	0.139 (2)	0.0523 (12)	0.0534 (13)	0.0117 (14)	0.0431 (15)	0.0011 (10)
C13	0.0991 (17)	0.0592 (12)	0.0537 (12)	0.0121 (12)	0.0293 (12)	0.0066 (10)
C14	0.0827 (14)	0.0383 (9)	0.0396 (9)	−0.0030 (9)	0.0199 (9)	0.0045 (7)
C15	0.0654 (12)	0.0482 (10)	0.0426 (10)	−0.0170 (9)	0.0037 (9)	0.0007 (8)
C16	0.0565 (13)	0.0702 (14)	0.0784 (15)	−0.0075 (11)	0.0065 (11)	0.0081 (12)
C17	0.0768 (17)	0.0912 (18)	0.104 (2)	0.0034 (14)	0.0249 (15)	−0.0120 (16)
C18	0.0572 (11)	0.0414 (9)	0.0389 (9)	−0.0050 (8)	0.0039 (8)	−0.0034 (7)
C19	0.0635 (12)	0.0429 (9)	0.0376 (9)	−0.0074 (8)	0.0051 (8)	−0.0013 (7)
C20	0.0440 (10)	0.0504 (10)	0.0390 (9)	−0.0034 (8)	0.0024 (7)	−0.0036 (7)
C21	0.0398 (9)	0.0587 (11)	0.0394 (9)	−0.0019 (8)	0.0019 (7)	−0.0001 (8)
C22	0.0562 (12)	0.0771 (14)	0.0380 (9)	0.0023 (10)	0.0074 (8)	−0.0026 (9)
C23	0.0654 (13)	0.0780 (15)	0.0504 (11)	0.0045 (11)	0.0079 (10)	−0.0189 (11)
C24	0.0672 (14)	0.0521 (11)	0.0745 (14)	0.0019 (10)	0.0106 (11)	−0.0151 (10)
C25	0.0615 (12)	0.0514 (10)	0.0507 (10)	−0.0026 (9)	0.0085 (9)	0.0002 (9)
C26	0.0654 (13)	0.0607 (12)	0.0528 (11)	−0.0022 (10)	0.0115 (10)	0.0078 (9)
N1	0.0647 (10)	0.0456 (8)	0.0386 (8)	0.0016 (7)	0.0102 (7)	0.0027 (6)
O1	0.0589 (9)	0.0704 (10)	0.0881 (11)	−0.0103 (7)	0.0267 (8)	0.0072 (8)
O2	0.0694 (9)	0.0408 (7)	0.0699 (9)	−0.0097 (6)	−0.0036 (7)	−0.0054 (6)
O3	0.0824 (11)	0.1226 (15)	0.0535 (9)	−0.0018 (10)	−0.0107 (8)	−0.0151 (9)
O4	0.0587 (9)	0.0764 (9)	0.0504 (8)	0.0003 (7)	0.0037 (6)	−0.0047 (7)
S1	0.0530 (3)	0.0423 (2)	0.0579 (3)	−0.0081 (2)	0.0101 (2)	0.0021 (2)

Geometric parameters (Å, º) top

C1—C6	1.377 (3)	C15—O4	1.318 (2)
C1—C2	1.381 (2)	C16—O4	1.444 (2)
C1—S1	1.7523 (17)	C16—C17	1.485 (3)
C2—C3	1.379 (3)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.368 (3)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.371 (3)	C17—H17C	0.9600
C4—H4	0.9300	C18—C19	1.313 (2)
C5—C6	1.379 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.472 (2)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.366 (2)	C20—C25	1.389 (3)
C7—N1	1.412 (2)	C20—C21	1.408 (2)
C7—C18	1.471 (2)	C21—C22	1.382 (3)
C8—C9	1.440 (2)	C21—C26	1.503 (3)
C8—C15	1.475 (3)	C22—C23	1.370 (3)
C9—C14	1.394 (3)	C22—H22	0.9300
C9—C10	1.404 (3)	C23—C24	1.368 (3)
C10—C11	1.368 (3)	C23—H23	0.9300
C10—H10	0.9300	C24—C25	1.380 (3)
C11—C12	1.379 (4)	C24—H24	0.9300
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.383 (3)	C26—H26A	0.9600
C12—H12	0.9300	C26—H26B	0.9600
C13—C14	1.388 (3)	C26—H26C	0.9600
C13—H13	0.9300	N1—S1	1.6789 (17)
C14—N1	1.425 (2)	O1—S1	1.4217 (14)
C15—O3	1.202 (2)	O2—S1	1.4194 (14)

C6—C1—C2	121.21 (17)	C17—C16—H16B	110.3
C6—C1—S1	119.25 (13)	H16A—C16—H16B	108.5
C2—C1—S1	119.54 (14)	C16—C17—H17A	109.5
C3—C2—C1	118.89 (18)	C16—C17—H17B	109.5
C3—C2—H2	120.6	H17A—C17—H17B	109.5
C1—C2—H2	120.6	C16—C17—H17C	109.5
C4—C3—C2	120.21 (18)	H17A—C17—H17C	109.5
C4—C3—H3	119.9	H17B—C17—H17C	109.5
C2—C3—H3	119.9	C19—C18—C7	124.04 (16)
C3—C4—C5	120.57 (18)	C19—C18—H18	118.0
C3—C4—H4	119.7	C7—C18—H18	118.0
C5—C4—H4	119.7	C18—C19—C20	125.73 (17)
C4—C5—C6	120.19 (19)	C18—C19—H19	117.1
C4—C5—H5	119.9	C20—C19—H19	117.1
C6—C5—H5	119.9	C25—C20—C21	118.73 (16)
C1—C6—C5	118.93 (18)	C25—C20—C19	120.03 (16)
C1—C6—H6	120.5	C21—C20—C19	121.24 (16)
C5—C6—H6	120.5	C22—C21—C20	118.50 (18)
C8—C7—N1	108.42 (15)	C22—C21—C26	119.57 (17)
C8—C7—C18	129.95 (17)	C20—C21—C26	121.89 (16)
N1—C7—C18	121.54 (16)	C23—C22—C21	121.92 (19)
C7—C8—C9	108.39 (18)	C23—C22—H22	119.0
C7—C8—C15	129.07 (16)	C21—C22—H22	119.0
C9—C8—C15	122.45 (17)	C24—C23—C22	119.83 (19)
C14—C9—C10	119.08 (19)	C24—C23—H23	120.1
C14—C9—C8	107.85 (16)	C22—C23—H23	120.1
C10—C9—C8	133.1 (2)	C23—C24—C25	119.8 (2)
C11—C10—C9	118.5 (2)	C23—C24—H24	120.1
C11—C10—H10	120.8	C25—C24—H24	120.1
C9—C10—H10	120.8	C24—C25—C20	121.19 (19)
C10—C11—C12	121.6 (2)	C24—C25—H25	119.4
C10—C11—H11	119.2	C20—C25—H25	119.4
C12—C11—H11	119.2	C21—C26—H26A	109.5
C11—C12—C13	121.6 (2)	C21—C26—H26B	109.5
C11—C12—H12	119.2	H26A—C26—H26B	109.5
C13—C12—H12	119.2	C21—C26—H26C	109.5
C12—C13—C14	116.9 (2)	H26A—C26—H26C	109.5
C12—C13—H13	121.5	H26B—C26—H26C	109.5
C14—C13—H13	121.5	C7—N1—C14	108.25 (16)
C13—C14—C9	122.30 (19)	C7—N1—S1	126.20 (12)
C13—C14—N1	130.7 (2)	C14—N1—S1	124.06 (14)
C9—C14—N1	106.99 (16)	C15—O4—C16	116.92 (16)
O3—C15—O4	122.5 (2)	O2—S1—O1	120.39 (9)
O3—C15—C8	122.88 (19)	O2—S1—N1	107.11 (8)
O4—C15—C8	114.58 (16)	O1—S1—N1	105.37 (9)
O4—C16—C17	107.22 (19)	O2—S1—C1	109.27 (8)
O4—C16—H16A	110.3	O1—S1—C1	108.67 (9)
C17—C16—H16A	110.3	N1—S1—C1	104.91 (8)
O4—C16—H16B	110.3

C6—C1—C2—C3	0.2 (3)	C18—C19—C20—C21	−146.01 (19)
S1—C1—C2—C3	179.60 (15)	C25—C20—C21—C22	−1.4 (3)
C1—C2—C3—C4	−0.2 (3)	C19—C20—C21—C22	178.96 (17)
C2—C3—C4—C5	−0.4 (3)	C25—C20—C21—C26	−178.99 (18)
C3—C4—C5—C6	0.8 (3)	C19—C20—C21—C26	1.4 (3)
C2—C1—C6—C5	0.3 (3)	C20—C21—C22—C23	0.0 (3)
S1—C1—C6—C5	−179.13 (16)	C26—C21—C22—C23	177.64 (19)
C4—C5—C6—C1	−0.8 (3)	C21—C22—C23—C24	1.0 (3)
N1—C7—C8—C9	1.62 (18)	C22—C23—C24—C25	−0.6 (3)
C18—C7—C8—C9	178.34 (16)	C23—C24—C25—C20	−0.8 (3)
N1—C7—C8—C15	−174.87 (16)	C21—C20—C25—C24	1.8 (3)
C18—C7—C8—C15	1.8 (3)	C19—C20—C25—C24	−178.52 (18)
C7—C8—C9—C14	0.51 (19)	C8—C7—N1—C14	−3.13 (18)
C15—C8—C9—C14	177.28 (15)	C18—C7—N1—C14	179.82 (14)
C7—C8—C9—C10	−179.41 (18)	C8—C7—N1—S1	−169.56 (12)
C15—C8—C9—C10	−2.6 (3)	C18—C7—N1—S1	13.4 (2)
C14—C9—C10—C11	1.0 (3)	C13—C14—N1—C7	−177.09 (18)
C8—C9—C10—C11	−179.08 (19)	C9—C14—N1—C7	3.40 (18)
C9—C10—C11—C12	1.0 (3)	C13—C14—N1—S1	−10.3 (3)
C10—C11—C12—C13	−2.2 (4)	C9—C14—N1—S1	170.19 (12)
C11—C12—C13—C14	1.2 (3)	O3—C15—O4—C16	1.7 (3)
C12—C13—C14—C9	0.9 (3)	C8—C15—O4—C16	−178.92 (16)
C12—C13—C14—N1	−178.54 (18)	C17—C16—O4—C15	−177.89 (18)
C10—C9—C14—C13	−2.0 (3)	C7—N1—S1—O2	−32.90 (16)
C8—C9—C14—C13	178.05 (17)	C14—N1—S1—O2	162.70 (14)
C10—C9—C14—N1	177.54 (15)	C7—N1—S1—O1	−162.21 (14)
C8—C9—C14—N1	−2.39 (18)	C14—N1—S1—O1	33.38 (16)
C7—C8—C15—O3	169.53 (19)	C7—N1—S1—C1	83.16 (15)
C9—C8—C15—O3	−6.5 (3)	C14—N1—S1—C1	−81.24 (15)
C7—C8—C15—O4	−9.8 (3)	C6—C1—S1—O2	17.63 (18)
C9—C8—C15—O4	174.12 (15)	C2—C1—S1—O2	−161.76 (15)
C8—C7—C18—C19	67.2 (3)	C6—C1—S1—O1	150.76 (16)
N1—C7—C18—C19	−116.4 (2)	C2—C1—S1—O1	−28.63 (18)
C7—C18—C19—C20	−176.79 (17)	C6—C1—S1—N1	−96.93 (16)
C18—C19—C20—C25	34.3 (3)	C2—C1—S1—N1	83.68 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3	0.93	2.48	3.000 (3)	116
C13—H13···O1	0.93	2.33	2.908 (3)	120
C16—H16A···O1ⁱ	0.97	2.56	3.381 (3)	143

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₃NO₄S
M_r	445.51
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	10.4248 (4), 8.3629 (3), 25.2284 (11)
β (°)	92.902 (1)
V (Å³)	2196.63 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.958, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	22952, 4848, 3551
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.117, 1.03
No. of reflections	4848
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3	0.93	2.48	3.000 (3)	116
C13—H13···O1	0.93	2.33	2.908 (3)	120
C16—H16A···O1ⁱ	0.97	2.56	3.381 (3)	143

Symmetry code: (i) x−1, y, z.

Acknowledgements

CR wishes to acknowledge AMET University management, India, for their kind support.

References

Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Giorgi, G., Salvini, L. & Garaliene, V. (2001). Anticancer Drug Des. 16, 167–174. Web of Science PubMed CAS Google Scholar
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, o542. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chakkaravarthi, G., Ramesh, N., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3564. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kolocouris, N., Foscolos, G. B., Kolocouris, A., Marakos, P., Pouli, N., Fytas, G., Ikeda, S. & De Clercq, E. (1994). J. Med. Chem. 37, 2896–2902. CrossRef CAS PubMed Web of Science Google Scholar
Merck (1973). French Patent No. 2 163 554. 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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Volume 67| Part 2| February 2011| Page o448

doi:10.1107/S1600536811001863

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 1-benzene­sulfonyl-2-[(E)-2-(2-methyl­phen­yl)ethen­yl]indole-3-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

Ethyl 1-benzenesulfonyl-2-[(E)-2-(2-methylphenyl)ethenyl]indole-3-carboxylate