1-{2-[(E)-2-(2-Nitro-phen-yl)ethen-yl]-1-phenyl-sulfonyl-1H-indol-3-yl}ethanone.

In the title compound, C24H18N2O5S, the S atom has a distorted tetra-hedral configuration, with bond angles varying from 105.11 (7) to 119.98 (8)°. As a result of the electron-withdrawing character of the phenyl-sulfonyl group, the N-Csp (2) bond lengths [1.414 (2) and 1.413 (2) Å] are slightly longer than the reported value of 1.355 (14) Å for N atoms with a planar configuration. The indole moiety is essentially planar, with a maximum deviation of 0.0177 (14) Å for the N atom. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 85.70 (7)° with the mean plane of the indole moiety. The mol-ecular structure features intra-molecular C-H⋯O hydrogen bonds, which generate S(6) and S(12) ring motifs. In the crystal, adjacent mol-ecules are linked via C-H⋯O hydrogen bonds, forming infinite C(7) chains running along the a-axis direction. The crystal packing also features C-H⋯π inter-actions, which form a three-dimensional structure.

Related literature

For the biological activity of Indole derivatives, see: Rodriguez et al. (1985 ▶); Chai et al. (2006 ▶); Olgen & Coban (2003 ▶). For related crystal structures, see: Karthikeyan et al. (2011 ▶, 2012 ▶). For related bond distances and bond-angle geometries and distortions, see: Allen (1981 ▶); Allen et al. (1987 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For the Thorpe–Ingold effect, see: Bassindale (1984 ▶).

Experimental

Crystal data

C24H18N2O5S

M = 446.46

Monoclinic,

a = 8.2409 (8) Å

b = 16.1702 (15) Å

c = 15.3700 (15) Å

β = 95.775 (5)°

V = 2037.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.28 × 0.25 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

18837 measured reflections

4960 independent reflections

3893 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.118

S = 1.02

4960 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.38 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 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813022241/su2631sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022241/su2631Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022241/su2631Isup3.cml

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

C24H18N2O5S	F(000) = 928
Mr = 446.46	Dx = 1.455 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 4960 reflections
a = 8.2409 (8) Å	θ = 1.8–28.4°
b = 16.1702 (15) Å	µ = 0.20 mm−1
c = 15.3700 (15) Å	T = 296 K
β = 95.775 (5)°	Block, yellow
V = 2037.8 (3) Å3	0.28 × 0.25 × 0.23 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3893 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 28.4°, θmin = 1.8°
ω and φ scans	h = −10→7
18837 measured reflections	k = −17→21
4960 independent reflections	l = −19→20

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.059P)2 + 0.5665P] where P = (Fo2 + 2Fc2)/3
4960 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.38 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	0.21108 (19)	0.10784 (11)	0.52063 (10)	0.0405 (4)
C2	0.1313 (3)	0.17176 (13)	0.47358 (13)	0.0570 (5)
H2	0.1284	0.2250	0.4963	0.068*
C3	0.0567 (2)	0.15297 (15)	0.39184 (13)	0.0627 (5)
H3	0.0019	0.1944	0.3587	0.075*
C4	0.0611 (2)	0.07382 (14)	0.35767 (12)	0.0579 (5)
H4	0.0089	0.0631	0.3023	0.070*
C5	0.1414 (2)	0.01077 (13)	0.40421 (11)	0.0499 (4)
H5	0.1450	−0.0421	0.3806	0.060*
C6	0.21746 (19)	0.02793 (11)	0.48764 (10)	0.0395 (4)
C7	0.31131 (18)	−0.02214 (10)	0.55255 (10)	0.0379 (3)
C8	0.35638 (18)	0.02700 (9)	0.62314 (10)	0.0356 (3)
C9	0.45622 (19)	0.00804 (10)	0.70516 (10)	0.0375 (3)
H9	0.5562	0.0346	0.7165	0.045*
C10	0.41139 (19)	−0.04492 (10)	0.76375 (10)	0.0381 (3)
H10	0.3066	−0.0668	0.7559	0.046*
C11	0.5202 (2)	−0.07076 (9)	0.84085 (10)	0.0386 (3)
C12	0.6855 (2)	−0.08209 (11)	0.83104 (13)	0.0500 (4)
H12	0.7229	−0.0696	0.7775	0.060*
C13	0.7946 (2)	−0.11089 (13)	0.89725 (15)	0.0618 (5)
H13	0.9040	−0.1172	0.8885	0.074*
C14	0.7415 (3)	−0.13056 (13)	0.97719 (14)	0.0652 (6)
H14	0.8147	−0.1514	1.0218	0.078*
C15	0.5818 (3)	−0.11937 (12)	0.99067 (12)	0.0566 (5)
H15	0.5464	−0.1316	1.0448	0.068*
C16	0.4726 (2)	−0.08979 (10)	0.92347 (10)	0.0422 (4)
C17	0.10318 (18)	0.16933 (9)	0.72059 (10)	0.0339 (3)
C18	0.0997 (2)	0.11710 (11)	0.79151 (10)	0.0426 (4)
H18	0.1937	0.0897	0.8143	0.051*
C19	−0.0445 (2)	0.10613 (12)	0.82802 (11)	0.0478 (4)
H19	−0.0483	0.0711	0.8757	0.057*
C20	−0.1833 (2)	0.14712 (12)	0.79391 (11)	0.0460 (4)
H20	−0.2800	0.1404	0.8195	0.055*
C21	−0.1796 (2)	0.19756 (12)	0.72260 (12)	0.0466 (4)
H21	−0.2743	0.2241	0.6994	0.056*
C22	−0.03571 (19)	0.20929 (10)	0.68482 (11)	0.0415 (4)
H22	−0.0328	0.2434	0.6363	0.050*
C23	0.3572 (2)	−0.10893 (11)	0.53594 (12)	0.0513 (4)
C24	0.4614 (3)	−0.15953 (12)	0.59949 (13)	0.0617 (5)
H24A	0.3984	−0.1781	0.6450	0.093*
H24B	0.5515	−0.1268	0.6245	0.093*
H24C	0.5018	−0.2065	0.5702	0.093*
N1	0.30044 (16)	0.10825 (8)	0.60412 (8)	0.0394 (3)
N2	0.3042 (2)	−0.07812 (9)	0.94350 (10)	0.0501 (4)
O1	0.28218 (16)	0.25924 (7)	0.62838 (9)	0.0549 (3)
O2	0.41828 (14)	0.17130 (8)	0.74404 (8)	0.0498 (3)
O3	0.20813 (17)	−0.04423 (10)	0.89080 (9)	0.0653 (4)
O4	0.2671 (2)	−0.10333 (12)	1.01319 (10)	0.0862 (5)
O5	0.3144 (3)	−0.13858 (12)	0.46632 (13)	0.1255 (10)
S1	0.28946 (5)	0.18452 (2)	0.67705 (3)	0.03893 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0387 (8)	0.0493 (9)	0.0345 (8)	0.0064 (7)	0.0078 (6)	0.0042 (7)
C2	0.0639 (12)	0.0574 (11)	0.0499 (10)	0.0185 (9)	0.0072 (9)	0.0088 (9)
C3	0.0602 (12)	0.0790 (14)	0.0479 (11)	0.0200 (11)	0.0012 (9)	0.0180 (10)
C4	0.0465 (10)	0.0853 (15)	0.0409 (10)	0.0039 (10)	−0.0008 (8)	0.0064 (9)
C5	0.0443 (9)	0.0639 (11)	0.0414 (9)	−0.0026 (8)	0.0030 (7)	−0.0025 (8)
C6	0.0354 (8)	0.0484 (9)	0.0356 (8)	−0.0002 (7)	0.0080 (6)	0.0027 (7)
C7	0.0364 (8)	0.0411 (8)	0.0367 (8)	−0.0010 (6)	0.0060 (6)	0.0015 (6)
C8	0.0336 (7)	0.0380 (8)	0.0363 (8)	0.0016 (6)	0.0089 (6)	0.0037 (6)
C9	0.0354 (8)	0.0392 (8)	0.0378 (8)	0.0019 (6)	0.0028 (6)	−0.0007 (6)
C10	0.0350 (8)	0.0430 (9)	0.0363 (8)	0.0012 (6)	0.0033 (6)	−0.0008 (7)
C11	0.0429 (9)	0.0342 (8)	0.0376 (8)	−0.0022 (6)	−0.0006 (6)	−0.0016 (6)
C12	0.0441 (9)	0.0502 (10)	0.0547 (10)	−0.0022 (8)	0.0004 (8)	0.0038 (8)
C13	0.0457 (10)	0.0613 (12)	0.0743 (14)	−0.0011 (9)	−0.0142 (9)	−0.0001 (10)
C14	0.0725 (14)	0.0595 (12)	0.0569 (12)	0.0018 (10)	−0.0271 (10)	0.0017 (10)
C15	0.0834 (15)	0.0468 (10)	0.0369 (9)	−0.0011 (9)	−0.0081 (9)	−0.0002 (8)
C16	0.0551 (10)	0.0337 (8)	0.0370 (8)	−0.0014 (7)	0.0014 (7)	−0.0035 (6)
C17	0.0335 (7)	0.0331 (7)	0.0347 (7)	−0.0002 (6)	0.0020 (6)	−0.0054 (6)
C18	0.0422 (9)	0.0481 (9)	0.0366 (8)	0.0067 (7)	−0.0005 (7)	0.0026 (7)
C19	0.0499 (10)	0.0556 (10)	0.0382 (9)	0.0001 (8)	0.0066 (7)	0.0065 (8)
C20	0.0377 (9)	0.0561 (10)	0.0446 (9)	−0.0045 (7)	0.0062 (7)	−0.0037 (8)
C21	0.0349 (8)	0.0533 (10)	0.0506 (10)	0.0052 (7)	−0.0008 (7)	0.0015 (8)
C22	0.0417 (9)	0.0401 (8)	0.0419 (9)	0.0022 (7)	−0.0007 (7)	0.0050 (7)
C23	0.0586 (11)	0.0445 (10)	0.0495 (10)	−0.0001 (8)	−0.0006 (8)	−0.0066 (8)
C24	0.0823 (15)	0.0428 (10)	0.0596 (12)	0.0124 (10)	0.0054 (10)	−0.0016 (9)
N1	0.0437 (7)	0.0401 (7)	0.0349 (7)	0.0076 (6)	0.0060 (5)	0.0013 (5)
N2	0.0696 (10)	0.0408 (8)	0.0419 (8)	0.0020 (7)	0.0159 (7)	0.0004 (6)
O1	0.0575 (8)	0.0386 (6)	0.0708 (8)	−0.0015 (5)	0.0165 (6)	0.0090 (6)
O2	0.0369 (6)	0.0521 (7)	0.0589 (8)	−0.0016 (5)	−0.0030 (5)	−0.0118 (6)
O3	0.0606 (9)	0.0722 (10)	0.0661 (9)	0.0154 (7)	0.0206 (7)	0.0209 (7)
O4	0.1070 (13)	0.1054 (13)	0.0524 (9)	0.0156 (11)	0.0377 (9)	0.0191 (9)
O5	0.191 (2)	0.0768 (12)	0.0917 (13)	0.0510 (14)	−0.0689 (14)	−0.0432 (11)
S1	0.0365 (2)	0.0349 (2)	0.0456 (2)	−0.00095 (15)	0.00548 (16)	−0.00227 (16)

C1—C2	1.389 (2)	C14—H14	0.9300
C1—C6	1.391 (2)	C15—C16	1.385 (2)
C1—N1	1.414 (2)	C15—H15	0.9300
C2—C3	1.376 (3)	C16—N2	1.464 (2)
C2—H2	0.9300	C17—C22	1.380 (2)
C3—C4	1.385 (3)	C17—C18	1.382 (2)
C3—H3	0.9300	C17—S1	1.7526 (15)
C4—C5	1.376 (3)	C18—C19	1.375 (2)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.397 (2)	C19—C20	1.379 (2)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.447 (2)	C20—C21	1.369 (3)
C7—C8	1.366 (2)	C20—H20	0.9300
C7—C23	1.482 (2)	C21—C22	1.385 (2)
C8—N1	1.413 (2)	C21—H21	0.9300
C8—C9	1.467 (2)	C22—H22	0.9300
C9—C10	1.322 (2)	C23—O5	1.193 (2)
C9—H9	0.9300	C23—C24	1.480 (3)
C10—C11	1.473 (2)	C24—H24A	0.9600
C10—H10	0.9300	C24—H24B	0.9600
C11—C12	1.397 (2)	C24—H24C	0.9600
C11—C16	1.401 (2)	N1—S1	1.6752 (14)
C12—C13	1.370 (3)	N2—O3	1.2058 (19)
C12—H12	0.9300	N2—O4	1.2135 (19)
C13—C14	1.382 (3)	O1—S1	1.4192 (13)
C13—H13	0.9300	O2—S1	1.4187 (12)
C14—C15	1.365 (3)
C2—C1—C6	122.34 (16)	C16—C15—H15	120.1
C2—C1—N1	130.19 (17)	C15—C16—C11	122.11 (17)
C6—C1—N1	107.45 (13)	C15—C16—N2	116.51 (16)
C3—C2—C1	117.12 (19)	C11—C16—N2	121.38 (15)
C3—C2—H2	121.4	C22—C17—C18	121.22 (15)
C1—C2—H2	121.4	C22—C17—S1	120.38 (12)
C2—C3—C4	121.59 (18)	C18—C17—S1	118.40 (12)
C2—C3—H3	119.2	C19—C18—C17	119.23 (15)
C4—C3—H3	119.2	C19—C18—H18	120.4
C5—C4—C3	121.13 (18)	C17—C18—H18	120.4
C5—C4—H4	119.4	C18—C19—C20	120.04 (16)
C3—C4—H4	119.4	C18—C19—H19	120.0
C4—C5—C6	118.54 (18)	C20—C19—H19	120.0
C4—C5—H5	120.7	C21—C20—C19	120.40 (16)
C6—C5—H5	120.7	C21—C20—H20	119.8
C1—C6—C5	119.28 (16)	C19—C20—H20	119.8
C1—C6—C7	107.80 (14)	C20—C21—C22	120.41 (16)
C5—C6—C7	132.91 (16)	C20—C21—H21	119.8
C8—C7—C6	107.81 (14)	C22—C21—H21	119.8
C8—C7—C23	129.34 (15)	C17—C22—C21	118.68 (15)
C6—C7—C23	122.62 (15)	C17—C22—H22	120.7
C7—C8—N1	108.64 (13)	C21—C22—H22	120.7
C7—C8—C9	130.18 (14)	O5—C23—C24	117.99 (18)
N1—C8—C9	121.02 (14)	O5—C23—C7	118.50 (18)
C10—C9—C8	123.36 (15)	C24—C23—C7	123.42 (16)
C10—C9—H9	118.3	C23—C24—H24A	109.5
C8—C9—H9	118.3	C23—C24—H24B	109.5
C9—C10—C11	122.86 (15)	H24A—C24—H24B	109.5
C9—C10—H10	118.6	C23—C24—H24C	109.5
C11—C10—H10	118.6	H24A—C24—H24C	109.5
C12—C11—C16	115.74 (15)	H24B—C24—H24C	109.5
C12—C11—C10	118.13 (15)	C8—N1—C1	108.22 (13)
C16—C11—C10	126.03 (15)	C8—N1—S1	125.77 (11)
C13—C12—C11	122.58 (19)	C1—N1—S1	123.54 (11)
C13—C12—H12	118.7	O3—N2—O4	122.63 (17)
C11—C12—H12	118.7	O3—N2—C16	119.31 (14)
C12—C13—C14	119.7 (2)	O4—N2—C16	118.06 (17)
C12—C13—H13	120.1	O2—S1—O1	119.98 (8)
C14—C13—H13	120.1	O2—S1—N1	106.73 (7)
C15—C14—C13	120.05 (18)	O1—S1—N1	106.04 (8)
C15—C14—H14	120.0	O2—S1—C17	108.79 (7)
C13—C14—H14	120.0	O1—S1—C17	109.17 (8)
C14—C15—C16	119.79 (19)	N1—S1—C17	105.11 (7)
C14—C15—H15	120.1
C6—C1—C2—C3	0.3 (3)	S1—C17—C18—C19	178.28 (13)
N1—C1—C2—C3	178.49 (17)	C17—C18—C19—C20	−0.1 (3)
C1—C2—C3—C4	−0.2 (3)	C18—C19—C20—C21	1.3 (3)
C2—C3—C4—C5	−0.3 (3)	C19—C20—C21—C22	−1.2 (3)
C3—C4—C5—C6	0.7 (3)	C18—C17—C22—C21	1.4 (2)
C2—C1—C6—C5	0.1 (3)	S1—C17—C22—C21	−178.17 (13)
N1—C1—C6—C5	−178.46 (14)	C20—C21—C22—C17	−0.1 (3)
C2—C1—C6—C7	179.14 (16)	C8—C7—C23—O5	−174.0 (2)
N1—C1—C6—C7	0.59 (17)	C6—C7—C23—O5	−0.3 (3)
C4—C5—C6—C1	−0.6 (2)	C8—C7—C23—C24	2.5 (3)
C4—C5—C6—C7	−179.37 (18)	C6—C7—C23—C24	176.22 (17)
C1—C6—C7—C8	1.22 (17)	C7—C8—N1—C1	2.95 (17)
C5—C6—C7—C8	−179.90 (17)	C9—C8—N1—C1	178.81 (13)
C1—C6—C7—C23	−173.71 (15)	C7—C8—N1—S1	165.52 (11)
C5—C6—C7—C23	5.2 (3)	C9—C8—N1—S1	−18.6 (2)
C6—C7—C8—N1	−2.55 (17)	C2—C1—N1—C8	179.46 (18)
C23—C7—C8—N1	171.93 (16)	C6—C1—N1—C8	−2.14 (17)
C6—C7—C8—C9	−177.91 (15)	C2—C1—N1—S1	16.4 (3)
C23—C7—C8—C9	−3.4 (3)	C6—C1—N1—S1	−165.19 (11)
C7—C8—C9—C10	−65.7 (2)	C15—C16—N2—O3	172.02 (17)
N1—C8—C9—C10	119.47 (18)	C11—C16—N2—O3	−7.1 (2)
C8—C9—C10—C11	172.71 (14)	C15—C16—N2—O4	−8.0 (2)
C9—C10—C11—C12	−37.6 (2)	C11—C16—N2—O4	172.85 (17)
C9—C10—C11—C16	146.09 (17)	C8—N1—S1—O2	31.41 (15)
C16—C11—C12—C13	0.8 (3)	C1—N1—S1—O2	−168.55 (12)
C10—C11—C12—C13	−175.90 (17)	C8—N1—S1—O1	160.41 (13)
C11—C12—C13—C14	0.6 (3)	C1—N1—S1—O1	−39.55 (15)
C12—C13—C14—C15	−1.6 (3)	C8—N1—S1—C17	−84.02 (14)
C13—C14—C15—C16	1.3 (3)	C1—N1—S1—C17	76.02 (14)
C14—C15—C16—C11	0.1 (3)	C22—C17—S1—O2	152.91 (13)
C14—C15—C16—N2	−178.97 (17)	C18—C17—S1—O2	−26.65 (14)
C12—C11—C16—C15	−1.1 (2)	C22—C17—S1—O1	20.30 (15)
C10—C11—C16—C15	175.24 (16)	C18—C17—S1—O1	−159.27 (12)
C12—C11—C16—N2	177.94 (15)	C22—C17—S1—N1	−93.09 (13)
C10—C11—C16—N2	−5.7 (2)	C18—C17—S1—N1	87.35 (13)
C22—C17—C18—C19	−1.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.35	2.935 (2)	121
C18—H18···O3	0.93	2.46	3.108 (2)	127
C20—H20···O2i	0.93	2.68	3.319 (2)	126
C5—H5···Cg1ii	0.93	2.89	3.720 (2)	149
C22—H22···Cg2iii	0.93	2.73	3.4618 (18)	137
C24—H24B···Cg3iv	0.96	2.90	3.601 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C17–C22, C11–C16 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.35	2.935 (2)	121
C18—H18⋯O3	0.93	2.46	3.108 (2)	127
C20—H20⋯O2i	0.93	2.68	3.319 (2)	126
C5—H5⋯Cg1ii	0.93	2.89	3.720 (2)	149
C22—H22⋯Cg2iii	0.93	2.73	3.4618 (18)	137
C24—H24B⋯Cg3iv	0.96	2.90	3.601 (3)	131

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .