(E)-1-[2-(2-Nitro-styr-yl)-1-phenyl-sulfonyl-1H-indol-3-yl]propan-1-one.

In the title compound, C25H20N2O5S, the phenyl ring makes dihedral angles of 89.88 (8) and 13.98 (8)°, respectively, with the indole ring system and the nitro-benzene ring. The dihedral angle between the indole ring system and the nitro-benzene ring is 88.48 (11)°. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O inter-action. In the crystal, π-π inter-actions, with centroid-centroid distances of 3.6741 (18) and 3.8873 (17) Å, link the mol-ecules into layers parallel to the ab plane.

Related literature

For biological activity of indole derivatives, see: Andreani et al. (2001 ▶); Quetin-Leclercq (1994 ▶); Mukhopadhyay et al. (1981 ▶); Singh et al. (2000 ▶). For related structures, see: Umadevi et al. (2013 ▶); Kanchanadevi et al. (2014 ▶).

Experimental

Crystal data

C25H20N2O5S

M = 460.49

Monoclinic,

a = 21.6100 (18) Å

b = 8.3072 (7) Å

c = 25.898 (3) Å

β = 112.379 (2)°

V = 4299.1 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.19 mm−1

T = 295 K

0.30 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.945, T max = 0.955

40633 measured reflections

5343 independent reflections

3700 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.151

S = 1.04

5343 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.67 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814000506/is5331sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000506/is5331Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000506/is5331Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H20N2O5S	F(000) = 1920
Mr = 460.49	Dx = 1.423 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5350 reflections
a = 21.6100 (18) Å	θ = 2.0–28.3°
b = 8.3072 (7) Å	µ = 0.19 mm−1
c = 25.898 (3) Å	T = 295 K
β = 112.379 (2)°	Block, yellow
V = 4299.1 (7) Å3	0.30 × 0.25 × 0.25 mm
Z = 8

Bruker APEXII CCD diffractometer	5343 independent reflections
Radiation source: fine-focus sealed tube	3700 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 0 pixels mm-1	θmax = 28.3°, θmin = 2.0°
ω and φ scans	h = −28→28
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.945, Tmax = 0.955	l = −32→34
40633 measured reflections

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) = 0.151	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0587P)2 + 6.0066P] where P = (Fo2 + 2Fc2)/3
5343 reflections	(Δ/σ)max = 0.001
299 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.67 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.15190 (11)	−0.0496 (3)	0.50378 (9)	0.0411 (5)
C2	0.08840 (13)	−0.1098 (3)	0.47316 (10)	0.0544 (7)
H2	0.0544	−0.1071	0.4869	0.065*
C3	0.07820 (16)	−0.1738 (3)	0.42139 (11)	0.0649 (8)
H3	0.0364	−0.2157	0.3997	0.078*
C4	0.12856 (17)	−0.1769 (3)	0.40107 (11)	0.0647 (8)
H4	0.1199	−0.2207	0.3659	0.078*
C5	0.19136 (15)	−0.1172 (3)	0.43131 (10)	0.0561 (7)
H5	0.2249	−0.1208	0.4171	0.067*
C6	0.20352 (12)	−0.0506 (3)	0.48417 (9)	0.0433 (5)
C7	0.26149 (11)	0.0260 (3)	0.52583 (9)	0.0400 (5)
C8	0.24458 (10)	0.0690 (3)	0.56984 (8)	0.0356 (5)
C9	0.28201 (11)	0.1582 (3)	0.62103 (9)	0.0384 (5)
H9	0.2654	0.2575	0.6262	0.046*
C10	0.33832 (11)	0.1058 (3)	0.66058 (8)	0.0384 (5)
H10	0.3533	0.0032	0.6568	0.046*
C11	0.37820 (10)	0.2010 (3)	0.71009 (9)	0.0374 (5)
C12	0.37603 (13)	0.3685 (3)	0.70753 (11)	0.0503 (6)
H12	0.3482	0.4178	0.6746	0.060*
C13	0.41344 (15)	0.4635 (4)	0.75177 (14)	0.0651 (8)
H13	0.4098	0.5749	0.7487	0.078*
C14	0.45614 (14)	0.3952 (4)	0.80052 (12)	0.0661 (8)
H14	0.4814	0.4598	0.8304	0.079*
C15	0.46118 (13)	0.2320 (4)	0.80475 (10)	0.0566 (7)
H15	0.4906	0.1847	0.8374	0.068*
C16	0.42243 (11)	0.1363 (3)	0.76039 (9)	0.0415 (5)
C17	0.16595 (11)	−0.1823 (3)	0.63322 (9)	0.0372 (5)
C18	0.22218 (12)	−0.1958 (3)	0.68196 (10)	0.0479 (6)
H18	0.2470	−0.1051	0.6987	0.057*
C19	0.24071 (14)	−0.3460 (3)	0.70527 (11)	0.0578 (7)
H19	0.2782	−0.3571	0.7381	0.069*
C20	0.20406 (15)	−0.4794 (3)	0.68021 (11)	0.0549 (7)
H20	0.2169	−0.5802	0.6964	0.066*
C21	0.14871 (15)	−0.4656 (3)	0.63161 (11)	0.0548 (7)
H21	0.1243	−0.5567	0.6149	0.066*
C22	0.12933 (12)	−0.3159 (3)	0.60758 (10)	0.0473 (6)
H22	0.0920	−0.3055	0.5745	0.057*
C23	0.32263 (14)	0.0616 (4)	0.51526 (11)	0.0565 (7)
C25	0.43883 (15)	0.1576 (5)	0.53443 (13)	0.0788 (10)
H25A	0.4556	0.0538	0.5299	0.118*
H25B	0.4744	0.2201	0.5605	0.118*
H25C	0.4216	0.2120	0.4991	0.118*
N1	0.17663 (9)	0.0287 (2)	0.55666 (7)	0.0387 (4)
N2	0.42953 (12)	−0.0372 (3)	0.76957 (9)	0.0551 (6)
O1	0.07086 (8)	0.0081 (2)	0.57260 (8)	0.0582 (5)
O2	0.16992 (9)	0.1277 (2)	0.64547 (7)	0.0495 (4)
O3	0.38239 (11)	−0.1241 (2)	0.74363 (8)	0.0685 (6)
O4	0.48249 (12)	−0.0875 (3)	0.80380 (10)	0.0950 (8)
O5	0.32135 (15)	0.0336 (6)	0.46959 (12)	0.1606 (19)
C24	0.38311 (13)	0.1372 (4)	0.55629 (11)	0.0596 (7)
H24A	0.3994	0.0716	0.5898	0.072*
H24B	0.3714	0.2420	0.5664	0.072*
S1	0.14097 (3)	0.00862 (7)	0.60389 (2)	0.04073 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0433 (12)	0.0396 (12)	0.0310 (10)	0.0040 (9)	0.0034 (9)	0.0030 (9)
C2	0.0478 (14)	0.0557 (15)	0.0461 (13)	−0.0036 (12)	0.0025 (11)	0.0019 (12)
C3	0.0667 (18)	0.0546 (16)	0.0486 (15)	−0.0027 (14)	−0.0058 (14)	−0.0016 (13)
C4	0.089 (2)	0.0498 (15)	0.0366 (13)	0.0053 (15)	0.0028 (14)	−0.0063 (11)
C5	0.0748 (18)	0.0494 (14)	0.0405 (13)	0.0120 (13)	0.0180 (13)	−0.0017 (11)
C6	0.0512 (13)	0.0389 (12)	0.0339 (11)	0.0084 (10)	0.0095 (10)	0.0037 (9)
C7	0.0407 (12)	0.0423 (12)	0.0352 (11)	0.0064 (9)	0.0123 (9)	0.0031 (9)
C8	0.0356 (11)	0.0343 (10)	0.0332 (10)	0.0040 (8)	0.0090 (8)	0.0050 (8)
C9	0.0389 (11)	0.0376 (11)	0.0385 (11)	0.0001 (9)	0.0145 (9)	−0.0019 (9)
C10	0.0428 (12)	0.0363 (11)	0.0347 (10)	0.0010 (9)	0.0131 (9)	0.0001 (9)
C11	0.0344 (10)	0.0423 (12)	0.0367 (11)	−0.0020 (9)	0.0147 (9)	−0.0035 (9)
C12	0.0466 (13)	0.0431 (13)	0.0569 (15)	−0.0023 (11)	0.0149 (11)	−0.0004 (11)
C13	0.0616 (18)	0.0473 (15)	0.086 (2)	−0.0141 (13)	0.0275 (16)	−0.0191 (14)
C14	0.0574 (17)	0.078 (2)	0.0618 (17)	−0.0217 (15)	0.0214 (14)	−0.0309 (16)
C15	0.0452 (14)	0.085 (2)	0.0363 (12)	−0.0074 (13)	0.0113 (11)	−0.0076 (13)
C16	0.0363 (11)	0.0537 (14)	0.0349 (11)	−0.0011 (10)	0.0141 (9)	−0.0005 (10)
C17	0.0365 (11)	0.0407 (11)	0.0379 (11)	−0.0014 (9)	0.0182 (9)	−0.0015 (9)
C18	0.0489 (13)	0.0472 (13)	0.0415 (12)	−0.0043 (11)	0.0105 (11)	0.0003 (10)
C19	0.0615 (16)	0.0576 (16)	0.0476 (14)	0.0064 (13)	0.0131 (12)	0.0084 (12)
C20	0.0778 (19)	0.0422 (13)	0.0542 (15)	0.0059 (13)	0.0358 (14)	0.0061 (11)
C21	0.0716 (18)	0.0438 (14)	0.0562 (15)	−0.0095 (12)	0.0324 (14)	−0.0099 (11)
C22	0.0475 (13)	0.0507 (14)	0.0432 (13)	−0.0071 (11)	0.0168 (11)	−0.0063 (11)
C23	0.0539 (15)	0.0727 (18)	0.0490 (14)	0.0045 (13)	0.0263 (12)	−0.0045 (13)
C25	0.0535 (17)	0.117 (3)	0.071 (2)	−0.0062 (18)	0.0306 (15)	0.0107 (19)
N1	0.0353 (9)	0.0444 (10)	0.0335 (9)	−0.0002 (8)	0.0096 (7)	0.0003 (8)
N2	0.0550 (13)	0.0605 (14)	0.0427 (11)	0.0093 (11)	0.0106 (10)	0.0101 (10)
O1	0.0334 (9)	0.0724 (12)	0.0652 (11)	0.0094 (8)	0.0146 (8)	0.0086 (10)
O2	0.0594 (10)	0.0413 (9)	0.0533 (10)	0.0017 (8)	0.0276 (8)	−0.0066 (7)
O3	0.0716 (13)	0.0500 (11)	0.0676 (12)	−0.0019 (10)	0.0083 (10)	0.0098 (10)
O4	0.0792 (15)	0.0911 (17)	0.0785 (15)	0.0235 (13)	−0.0106 (12)	0.0267 (13)
O5	0.099 (2)	0.318 (5)	0.0942 (19)	−0.081 (3)	0.0701 (17)	−0.103 (3)
C24	0.0500 (15)	0.0769 (19)	0.0548 (15)	−0.0035 (13)	0.0232 (12)	0.0066 (14)
S1	0.0360 (3)	0.0430 (3)	0.0434 (3)	0.0043 (2)	0.0154 (2)	0.0012 (2)

C1—C6	1.390 (3)	C15—C16	1.386 (3)
C1—C2	1.390 (3)	C15—H15	0.9300
C1—N1	1.424 (3)	C16—N2	1.460 (3)
C2—C3	1.380 (4)	C17—C22	1.378 (3)
C2—H2	0.9300	C17—C18	1.384 (3)
C3—C4	1.378 (5)	C17—S1	1.753 (2)
C3—H3	0.9300	C18—C19	1.378 (4)
C4—C5	1.376 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.373 (4)
C5—C6	1.405 (3)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.372 (4)
C6—C7	1.452 (3)	C20—H20	0.9300
C7—C8	1.370 (3)	C21—C22	1.382 (4)
C7—C23	1.478 (4)	C21—H21	0.9300
C8—N1	1.415 (3)	C22—H22	0.9300
C8—C9	1.464 (3)	C23—O5	1.195 (3)
C9—C10	1.331 (3)	C23—C24	1.475 (4)
C9—H9	0.9300	C25—C24	1.523 (4)
C10—C11	1.474 (3)	C25—H25A	0.9600
C10—H10	0.9300	C25—H25B	0.9600
C11—C12	1.393 (3)	C25—H25C	0.9600
C11—C16	1.397 (3)	N1—S1	1.6838 (19)
C12—C13	1.372 (4)	N2—O3	1.220 (3)
C12—H12	0.9300	N2—O4	1.224 (3)
C13—C14	1.371 (4)	O1—S1	1.4204 (17)
C13—H13	0.9300	O2—S1	1.4198 (17)
C14—C15	1.361 (4)	C24—H24A	0.9700
C14—H14	0.9300	C24—H24B	0.9700
C6—C1—C2	123.0 (2)	C11—C16—N2	121.6 (2)
C6—C1—N1	107.12 (19)	C22—C17—C18	121.2 (2)
C2—C1—N1	129.8 (2)	C22—C17—S1	119.64 (17)
C3—C2—C1	116.8 (3)	C18—C17—S1	119.14 (17)
C3—C2—H2	121.6	C19—C18—C17	118.7 (2)
C1—C2—H2	121.6	C19—C18—H18	120.6
C4—C3—C2	121.4 (3)	C17—C18—H18	120.6
C4—C3—H3	119.3	C20—C19—C18	120.3 (2)
C2—C3—H3	119.3	C20—C19—H19	119.8
C5—C4—C3	121.8 (3)	C18—C19—H19	119.8
C5—C4—H4	119.1	C21—C20—C19	120.7 (2)
C3—C4—H4	119.1	C21—C20—H20	119.6
C4—C5—C6	118.3 (3)	C19—C20—H20	119.6
C4—C5—H5	120.8	C20—C21—C22	119.8 (2)
C6—C5—H5	120.8	C20—C21—H21	120.1
C1—C6—C5	118.6 (2)	C22—C21—H21	120.1
C1—C6—C7	108.1 (2)	C17—C22—C21	119.2 (2)
C5—C6—C7	133.2 (2)	C17—C22—H22	120.4
C8—C7—C6	107.7 (2)	C21—C22—H22	120.4
C8—C7—C23	130.0 (2)	O5—C23—C24	118.4 (3)
C6—C7—C23	122.0 (2)	O5—C23—C7	117.3 (3)
C7—C8—N1	108.57 (18)	C24—C23—C7	124.2 (2)
C7—C8—C9	130.9 (2)	C24—C25—H25A	109.5
N1—C8—C9	120.19 (19)	C24—C25—H25B	109.5
C10—C9—C8	124.0 (2)	H25A—C25—H25B	109.5
C10—C9—H9	118.0	C24—C25—H25C	109.5
C8—C9—H9	118.0	H25A—C25—H25C	109.5
C9—C10—C11	123.7 (2)	H25B—C25—H25C	109.5
C9—C10—H10	118.2	C8—N1—C1	108.36 (18)
C11—C10—H10	118.2	C8—N1—S1	124.61 (14)
C12—C11—C16	115.3 (2)	C1—N1—S1	123.06 (16)
C12—C11—C10	119.8 (2)	O3—N2—O4	123.5 (3)
C16—C11—C10	124.8 (2)	O3—N2—C16	118.7 (2)
C13—C12—C11	122.4 (3)	O4—N2—C16	117.8 (2)
C13—C12—H12	118.8	C23—C24—C25	112.9 (2)
C11—C12—H12	118.8	C23—C24—H24A	109.0
C14—C13—C12	120.4 (3)	C25—C24—H24A	109.0
C14—C13—H13	119.8	C23—C24—H24B	109.0
C12—C13—H13	119.8	C25—C24—H24B	109.0
C15—C14—C13	119.4 (3)	H24A—C24—H24B	107.8
C15—C14—H14	120.3	O2—S1—O1	120.06 (11)
C13—C14—H14	120.3	O2—S1—N1	106.89 (10)
C14—C15—C16	120.0 (3)	O1—S1—N1	105.65 (10)
C14—C15—H15	120.0	O2—S1—C17	109.13 (10)
C16—C15—H15	120.0	O1—S1—C17	109.28 (11)
C15—C16—C11	122.4 (2)	N1—S1—C17	104.71 (10)
C15—C16—N2	116.0 (2)
C6—C1—C2—C3	0.6 (4)	C17—C18—C19—C20	0.4 (4)
N1—C1—C2—C3	177.1 (2)	C18—C19—C20—C21	0.2 (4)
C1—C2—C3—C4	−0.3 (4)	C19—C20—C21—C22	−0.2 (4)
C2—C3—C4—C5	0.2 (4)	C18—C17—C22—C21	1.0 (4)
C3—C4—C5—C6	−0.4 (4)	S1—C17—C22—C21	−178.78 (19)
C2—C1—C6—C5	−0.8 (4)	C20—C21—C22—C17	−0.4 (4)
N1—C1—C6—C5	−178.0 (2)	C8—C7—C23—O5	−167.9 (4)
C2—C1—C6—C7	178.1 (2)	C6—C7—C23—O5	4.3 (5)
N1—C1—C6—C7	0.9 (2)	C8—C7—C23—C24	8.5 (4)
C4—C5—C6—C1	0.7 (4)	C6—C7—C23—C24	−179.2 (3)
C4—C5—C6—C7	−177.9 (2)	C7—C8—N1—C1	3.1 (2)
C1—C6—C7—C8	1.0 (3)	C9—C8—N1—C1	177.08 (18)
C5—C6—C7—C8	179.7 (2)	C7—C8—N1—S1	161.12 (16)
C1—C6—C7—C23	−172.8 (2)	C9—C8—N1—S1	−24.9 (3)
C5—C6—C7—C23	5.9 (4)	C6—C1—N1—C8	−2.4 (2)
C6—C7—C8—N1	−2.5 (2)	C2—C1—N1—C8	−179.3 (2)
C23—C7—C8—N1	170.6 (2)	C6—C1—N1—S1	−160.86 (16)
C6—C7—C8—C9	−175.6 (2)	C2—C1—N1—S1	22.2 (3)
C23—C7—C8—C9	−2.5 (4)	C15—C16—N2—O3	152.5 (2)
C7—C8—C9—C10	−64.8 (3)	C11—C16—N2—O3	−26.4 (4)
N1—C8—C9—C10	122.7 (2)	C15—C16—N2—O4	−26.3 (4)
C8—C9—C10—C11	175.6 (2)	C11—C16—N2—O4	154.8 (2)
C9—C10—C11—C12	−27.0 (3)	O5—C23—C24—C25	−4.3 (5)
C9—C10—C11—C16	156.7 (2)	C7—C23—C24—C25	179.3 (3)
C16—C11—C12—C13	−1.6 (4)	C8—N1—S1—O2	36.9 (2)
C10—C11—C12—C13	−178.2 (2)	C1—N1—S1—O2	−168.17 (17)
C11—C12—C13—C14	1.4 (4)	C8—N1—S1—O1	165.85 (18)
C12—C13—C14—C15	0.0 (5)	C1—N1—S1—O1	−39.2 (2)
C13—C14—C15—C16	−1.2 (4)	C8—N1—S1—C17	−78.81 (19)
C14—C15—C16—C11	1.1 (4)	C1—N1—S1—C17	76.13 (19)
C14—C15—C16—N2	−177.9 (2)	C22—C17—S1—O2	159.83 (18)
C12—C11—C16—C15	0.3 (3)	C18—C17—S1—O2	−20.0 (2)
C10—C11—C16—C15	176.8 (2)	C22—C17—S1—O1	26.7 (2)
C12—C11—C16—N2	179.2 (2)	C18—C17—S1—O1	−153.07 (19)
C10—C11—C16—N2	−4.4 (3)	C22—C17—S1—N1	−86.0 (2)
C22—C17—C18—C19	−1.0 (4)	C18—C17—S1—N1	94.2 (2)
S1—C17—C18—C19	178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.32	2.912 (3)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.32	2.912 (3)	121