(E)-3-Phenyl-2-(1-tosyl-1H-indol-3-ylcarbon-yl)acrylonitrile.

In the title compound, C(25)H(18)N(2)O(3)S, the indole moiety is planar and makes a dihedral angle of 89.95 (09)° with the phenyl ring of the sulfonyl substituent. The mol-ecular conformation features a weak C-H⋯N short contact and the crystal packing reveals a weak C-H⋯O hydrogen bond.

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001 ▶); Chai et al. (2006 ▶); Kolocouris et al. (1994 ▶); Ma et al. (2001 ▶); Nieto et al. (2005 ▶); Singh et al. (2000 ▶). For the bond-length difference, see: Allen (1981 ▶); Govindasamy et al. (1998 ▶); Sankaranarayanan et al. (2000 ▶). For the N atom-hybridization, see: Beddoes et al. (1986 ▶). For related structures, see: Seshadri et al. (2002 ▶).

Experimental

Crystal data

C25H18N2O3S

M = 426.47

Monoclinic,

a = 33.8741 (13) Å

b = 7.1294 (3) Å

c = 19.9180 (9) Å

β = 118.4170 (2)°

V = 4230.6 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.18 mm−1

T = 298 K

0.21 × 0.19 × 0.15 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

19948 measured reflections

5285 independent reflections

2177 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.176

S = 0.95

5285 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004886/kp2387sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004886/kp2387Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004886/kp2387Isup3.cml

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

C25H18N2O3S	F(000) = 1776
Mr = 426.47	Dx = 1.339 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5285 reflections
a = 33.8741 (13) Å	θ = 1.4–28.4°
b = 7.1294 (3) Å	µ = 0.18 mm−1
c = 19.9180 (9) Å	T = 298 K
β = 118.4170 (2)°	Block, colourless
V = 4230.6 (3) Å3	0.21 × 0.19 × 0.15 mm
Z = 8

Bruker SMART APEXII area-detector diffractometer	2177 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
Graphite monochromator	θmax = 28.4°, θmin = 1.4°
ω and φ scans	h = −44→45
19948 measured reflections	k = −9→9
5285 independent reflections	l = −26→21

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0805P)2] where P = (Fo2 + 2Fc2)/3
5285 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.31518 (8)	0.3247 (4)	0.26078 (18)	0.0600 (7)
C2	0.30356 (10)	0.4960 (4)	0.2794 (2)	0.0746 (9)
H2	0.3167	0.5385	0.3296	0.090*
C3	0.27188 (11)	0.5994 (4)	0.2206 (3)	0.0848 (10)
H3	0.2632	0.7148	0.2310	0.102*
C4	0.25246 (10)	0.5359 (4)	0.1457 (2)	0.0800 (9)
H4	0.2306	0.6085	0.1071	0.096*
C5	0.26497 (9)	0.3665 (4)	0.12750 (19)	0.0699 (8)
H5	0.2521	0.3259	0.0771	0.084*
C6	0.29717 (8)	0.2582 (4)	0.18621 (17)	0.0564 (7)
C7	0.31823 (8)	0.0804 (4)	0.18886 (16)	0.0555 (7)
C8	0.34654 (9)	0.0440 (4)	0.26354 (16)	0.0592 (7)
H8	0.3643	−0.0626	0.2817	0.071*
C9	0.30954 (9)	−0.0416 (4)	0.12459 (16)	0.0591 (7)
C10	0.34231 (8)	−0.1964 (4)	0.13431 (14)	0.0536 (7)
C11	0.38775 (10)	−0.1755 (4)	0.19112 (16)	0.0576 (7)
C12	0.32800 (9)	−0.3435 (4)	0.08643 (15)	0.0578 (7)
H12	0.2983	−0.3363	0.0482	0.069*
C13	0.35158 (9)	−0.5115 (4)	0.08504 (15)	0.0546 (7)
C14	0.33458 (9)	−0.6116 (4)	0.01750 (17)	0.0658 (8)
H14	0.3087	−0.5700	−0.0248	0.079*
C15	0.35560 (11)	−0.7728 (4)	0.0120 (2)	0.0774 (9)
H15	0.3440	−0.8379	−0.0339	0.093*
C16	0.39340 (11)	−0.8362 (4)	0.0741 (2)	0.0812 (9)
H16	0.4079	−0.9431	0.0700	0.097*
C17	0.41011 (11)	−0.7421 (4)	0.1426 (2)	0.0809 (9)
H17	0.4353	−0.7876	0.1852	0.097*
C18	0.38943 (10)	−0.5804 (4)	0.14814 (17)	0.0713 (8)
H18	0.4009	−0.5170	0.1945	0.086*
C19	0.42361 (9)	0.3581 (4)	0.39664 (15)	0.0606 (7)
C20	0.45161 (10)	0.2880 (5)	0.37005 (18)	0.0793 (9)
H20	0.4490	0.1638	0.3541	0.095*
C21	0.48304 (11)	0.4022 (6)	0.36733 (19)	0.0887 (10)
H21	0.5017	0.3542	0.3493	0.106*
C22	0.48793 (10)	0.5860 (5)	0.39046 (18)	0.0789 (10)
C23	0.45972 (10)	0.6538 (5)	0.41689 (19)	0.0803 (9)
H23	0.4625	0.7779	0.4329	0.096*
C24	0.42765 (10)	0.5417 (4)	0.42011 (17)	0.0716 (8)
H24	0.4089	0.5896	0.4380	0.086*
C25	0.52268 (11)	0.7124 (6)	0.3866 (2)	0.1128 (13)
H25A	0.5393	0.6429	0.3672	0.169*
H25B	0.5428	0.7582	0.4368	0.169*
H25C	0.5080	0.8164	0.3534	0.169*
N1	0.34515 (7)	0.1880 (3)	0.30873 (13)	0.0630 (6)
N2	0.42442 (9)	−0.1524 (3)	0.23564 (16)	0.0792 (8)
O1	0.36234 (7)	0.3040 (3)	0.43741 (12)	0.0896 (7)
O2	0.40187 (7)	0.0271 (3)	0.42345 (11)	0.0830 (6)
O3	0.27557 (7)	−0.0232 (3)	0.06329 (12)	0.0832 (6)
S1	0.38381 (3)	0.21122 (11)	0.40061 (4)	0.0698 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0581 (16)	0.0485 (17)	0.088 (2)	−0.0027 (14)	0.0464 (16)	−0.0045 (16)
C2	0.0714 (19)	0.064 (2)	0.105 (2)	−0.0046 (17)	0.0555 (19)	−0.0165 (19)
C3	0.079 (2)	0.058 (2)	0.142 (3)	−0.0015 (18)	0.072 (2)	−0.009 (2)
C4	0.0670 (19)	0.060 (2)	0.120 (3)	0.0096 (16)	0.051 (2)	0.013 (2)
C5	0.0605 (17)	0.0593 (19)	0.096 (2)	0.0004 (15)	0.0419 (17)	0.0019 (17)
C6	0.0508 (15)	0.0480 (16)	0.077 (2)	−0.0012 (13)	0.0361 (15)	0.0000 (15)
C7	0.0586 (16)	0.0462 (16)	0.0676 (18)	−0.0012 (13)	0.0347 (15)	−0.0047 (14)
C8	0.0658 (17)	0.0487 (16)	0.0690 (19)	0.0006 (13)	0.0370 (16)	−0.0050 (14)
C9	0.0588 (16)	0.0520 (17)	0.0646 (18)	−0.0011 (14)	0.0277 (15)	−0.0014 (14)
C10	0.0556 (15)	0.0493 (16)	0.0567 (16)	0.0007 (13)	0.0275 (14)	0.0008 (13)
C11	0.0592 (18)	0.0532 (17)	0.0608 (17)	0.0045 (14)	0.0288 (16)	−0.0009 (14)
C12	0.0603 (16)	0.0562 (17)	0.0595 (17)	−0.0012 (14)	0.0305 (14)	0.0026 (14)
C13	0.0584 (16)	0.0473 (16)	0.0651 (17)	−0.0017 (13)	0.0352 (14)	−0.0012 (14)
C14	0.0714 (18)	0.0610 (18)	0.0725 (19)	−0.0006 (15)	0.0403 (16)	−0.0085 (15)
C15	0.093 (2)	0.064 (2)	0.090 (2)	−0.0005 (18)	0.055 (2)	−0.0148 (18)
C16	0.090 (2)	0.059 (2)	0.117 (3)	0.0085 (18)	0.067 (2)	0.002 (2)
C17	0.082 (2)	0.060 (2)	0.099 (3)	0.0091 (17)	0.042 (2)	0.0116 (19)
C18	0.081 (2)	0.0520 (18)	0.080 (2)	0.0044 (16)	0.0374 (18)	0.0024 (15)
C19	0.0656 (17)	0.0619 (19)	0.0548 (16)	−0.0023 (15)	0.0290 (14)	−0.0033 (14)
C20	0.079 (2)	0.082 (2)	0.087 (2)	−0.0003 (18)	0.0478 (19)	−0.0138 (18)
C21	0.075 (2)	0.110 (3)	0.093 (2)	−0.002 (2)	0.050 (2)	−0.007 (2)
C22	0.0578 (18)	0.095 (3)	0.070 (2)	−0.0026 (18)	0.0193 (16)	0.0178 (19)
C23	0.072 (2)	0.065 (2)	0.089 (2)	−0.0021 (17)	0.0269 (18)	0.0049 (17)
C24	0.0721 (19)	0.067 (2)	0.080 (2)	−0.0013 (16)	0.0406 (17)	−0.0026 (17)
C25	0.073 (2)	0.143 (4)	0.111 (3)	−0.020 (2)	0.034 (2)	0.029 (3)
N1	0.0689 (14)	0.0563 (14)	0.0699 (15)	−0.0030 (12)	0.0381 (13)	−0.0106 (13)
N2	0.0704 (17)	0.0706 (17)	0.0851 (18)	0.0043 (14)	0.0276 (15)	0.0005 (14)
O1	0.1087 (16)	0.0969 (17)	0.0961 (16)	−0.0169 (13)	0.0755 (14)	−0.0299 (13)
O2	0.1187 (17)	0.0612 (13)	0.0717 (13)	−0.0003 (12)	0.0473 (12)	0.0074 (10)
O3	0.0740 (13)	0.0767 (14)	0.0737 (13)	0.0158 (11)	0.0147 (12)	−0.0106 (11)
S1	0.0880 (6)	0.0691 (6)	0.0650 (5)	−0.0087 (4)	0.0467 (4)	−0.0094 (4)

C1—C2	1.386 (4)	C14—H14	0.9300
C1—C6	1.393 (4)	C15—C16	1.366 (4)
C1—N1	1.404 (3)	C15—H15	0.9300
C2—C3	1.368 (5)	C16—C17	1.378 (5)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.389 (5)	C17—C18	1.380 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.384 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C24	1.375 (4)
C5—C6	1.393 (4)	C19—C20	1.381 (4)
C5—H5	0.9300	C19—S1	1.738 (3)
C6—C7	1.443 (3)	C20—C21	1.362 (4)
C7—C8	1.357 (4)	C20—H20	0.9300
C7—C9	1.457 (4)	C21—C22	1.373 (5)
C8—N1	1.381 (3)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.379 (4)
C9—O3	1.223 (3)	C22—C25	1.513 (4)
C9—C10	1.511 (3)	C23—C24	1.375 (4)
C10—C12	1.343 (3)	C23—H23	0.9300
C11—N2	1.144 (3)	C24—H24	0.9300
C11—N2	1.144 (3)	C25—H25A	0.9600
C12—C13	1.447 (4)	C25—H25B	0.9600
C12—H12	0.9300	C25—H25C	0.9600
C13—C14	1.383 (4)	N1—S1	1.676 (2)
C13—C18	1.390 (4)	O1—S1	1.418 (2)
C14—C15	1.383 (4)	O2—S1	1.428 (2)
C2—C1—C6	123.3 (3)	C14—C15—H15	120.0
C2—C1—N1	129.4 (3)	C15—C16—C17	120.1 (3)
C6—C1—N1	107.3 (2)	C15—C16—H16	120.0
C3—C2—C1	116.9 (3)	C17—C16—H16	120.0
C3—C2—H2	121.6	C16—C17—C18	120.1 (3)
C1—C2—H2	121.6	C16—C17—H17	120.0
C2—C3—C4	121.5 (3)	C18—C17—H17	120.0
C2—C3—H3	119.3	C17—C18—C13	120.5 (3)
C4—C3—H3	119.3	C17—C18—H18	119.7
C5—C4—C3	121.2 (3)	C13—C18—H18	119.7
C5—C4—H4	119.4	C24—C19—C20	120.0 (3)
C3—C4—H4	119.4	C24—C19—S1	120.8 (2)
C4—C5—C6	118.6 (3)	C20—C19—S1	119.2 (2)
C4—C5—H5	120.7	C21—C20—C19	119.4 (3)
C6—C5—H5	120.7	C21—C20—H20	120.3
C1—C6—C5	118.5 (3)	C19—C20—H20	120.3
C1—C6—C7	107.6 (2)	C20—C21—C22	122.0 (3)
C5—C6—C7	133.9 (3)	C20—C21—H21	119.0
C8—C7—C6	106.7 (2)	C22—C21—H21	119.0
C8—C7—C9	126.2 (2)	C21—C22—C23	117.9 (3)
C6—C7—C9	127.1 (3)	C21—C22—C25	121.6 (3)
C7—C8—N1	110.3 (2)	C23—C22—C25	120.5 (4)
C7—C8—H8	124.9	C24—C23—C22	121.4 (3)
N1—C8—H8	124.9	C24—C23—H23	119.3
O3—C9—C7	120.9 (2)	C22—C23—H23	119.3
O3—C9—C10	119.4 (2)	C23—C24—C19	119.4 (3)
C7—C9—C10	119.6 (2)	C23—C24—H24	120.3
C12—C10—C11	122.4 (2)	C19—C24—H24	120.3
C12—C10—C9	119.0 (2)	C22—C25—H25A	109.5
C11—C10—C9	118.5 (2)	C22—C25—H25B	109.5
N2—C11—C10	177.4 (3)	H25A—C25—H25B	109.5
N2—C11—C10	177.4 (3)	C22—C25—H25C	109.5
C10—C12—C13	130.1 (2)	H25A—C25—H25C	109.5
C10—C12—H12	115.0	H25B—C25—H25C	109.5
C13—C12—H12	115.0	C8—N1—C1	108.1 (2)
C14—C13—C18	118.4 (3)	C8—N1—S1	122.25 (19)
C14—C13—C12	117.9 (3)	C1—N1—S1	127.6 (2)
C18—C13—C12	123.7 (3)	O1—S1—O2	120.75 (13)
C15—C14—C13	120.9 (3)	O1—S1—N1	106.49 (12)
C15—C14—H14	119.5	O2—S1—N1	104.53 (12)
C13—C14—H14	119.5	O1—S1—C19	110.00 (14)
C16—C15—C14	120.0 (3)	O2—S1—C19	110.14 (13)
C16—C15—H15	120.0	N1—S1—C19	103.28 (12)
C6—C1—C2—C3	1.7 (4)	C14—C15—C16—C17	1.3 (5)
N1—C1—C2—C3	−177.8 (3)	C15—C16—C17—C18	−1.9 (5)
C1—C2—C3—C4	−0.3 (4)	C16—C17—C18—C13	0.3 (5)
C2—C3—C4—C5	−1.1 (5)	C14—C13—C18—C17	1.7 (4)
C3—C4—C5—C6	1.0 (4)	C12—C13—C18—C17	179.8 (2)
C2—C1—C6—C5	−1.8 (4)	S1—C19—C20—C21	−179.6 (2)
N1—C1—C6—C5	177.8 (2)	C19—C20—C21—C22	0.1 (5)
C2—C1—C6—C7	177.9 (2)	C20—C21—C22—C23	−0.1 (5)
N1—C1—C6—C7	−2.5 (3)	C20—C21—C22—C25	−179.5 (3)
C4—C5—C6—C1	0.4 (4)	C25—C22—C23—C24	179.3 (3)
C4—C5—C6—C7	−179.3 (3)	C22—C23—C24—C19	0.1 (5)
C1—C6—C7—C8	1.8 (3)	C20—C19—C24—C23	−0.1 (4)
C5—C6—C7—C8	−178.5 (3)	S1—C19—C24—C23	179.4 (2)
C1—C6—C7—C9	179.2 (2)	C7—C8—N1—C1	−1.1 (3)
C5—C6—C7—C9	−1.1 (5)	C7—C8—N1—S1	−166.10 (19)
C6—C7—C8—N1	−0.5 (3)	C2—C1—N1—C8	−178.2 (3)
C9—C7—C8—N1	−177.9 (2)	C6—C1—N1—C8	2.2 (3)
C8—C7—C9—O3	159.9 (3)	C2—C1—N1—S1	−14.2 (4)
C6—C7—C9—O3	−17.1 (4)	C6—C1—N1—S1	166.19 (18)
C8—C7—C9—C10	−18.5 (4)	C8—N1—S1—O1	−152.2 (2)
C6—C7—C9—C10	164.5 (2)	C1—N1—S1—O1	45.9 (2)
O3—C9—C10—C12	−20.6 (4)	C8—N1—S1—O2	−23.3 (2)
C7—C9—C10—C12	157.8 (2)	C1—N1—S1—O2	174.8 (2)
O3—C9—C10—C11	155.9 (3)	C8—N1—S1—C19	91.9 (2)
C7—C9—C10—C11	−25.7 (3)	C1—N1—S1—C19	−70.0 (2)
C11—C10—C12—C13	6.3 (4)	C24—C19—S1—O1	−6.2 (3)
C9—C10—C12—C13	−177.3 (2)	C20—C19—S1—O1	173.4 (2)
C10—C12—C13—C14	−159.8 (3)	C24—C19—S1—O2	−141.6 (2)
C10—C12—C13—C18	22.1 (4)	C20—C19—S1—O2	37.9 (3)
C18—C13—C14—C15	−2.2 (4)	C24—C19—S1—N1	107.2 (2)
C12—C13—C14—C15	179.6 (2)	C20—C19—S1—N1	−73.3 (2)
C13—C14—C15—C16	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···N2	0.93	2.73	3.433 (4)	133
C5—H5···O3i	0.93	2.86	3.551 (4)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯N2	0.93	2.73	3.433 (4)	133
C5—H5⋯O3i	0.93	2.86	3.551 (4)	132

Symmetry code: (i) .