Ethyl 1-benzene-sulfonyl-2-[(E)-2-(2-methyl-phen-yl)ethen-yl]indole-3-carboxyl-ate.

In the title compound, C(26)H(23)NO(4)S, 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 mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions. The crystal structure structure features short intramolecular C-H⋯O contacts and π-π stacking inter-actions 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 = 445.51

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.03

4848 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.28 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H23NO4S	F(000) = 936
Mr = 445.51	Dx = 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

Bruker Kappa APEXII diffractometer	4848 independent reflections
Radiation source: fine-focus sealed tube	3551 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω and φ scans	θmax = 27.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
Tmin = 0.958, Tmax = 0.968	k = −10→10
22952 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0499P)2 + 0.6907P] where P = (Fo2 + 2Fc2)/3
4848 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .