(E)-1-[2-(4-Chloro-2-nitro-styr-yl)-1-phenyl-sulfonyl-1H-indol-3-yl]propan-1-one.

In the title compound, C25H19ClN2O5S, the phenyl ring forms dihedral angles of 79.62 (12) and 80.02 (13)° with the indole ring system and the benzene ring, respectively. The nitro group is twisted at an angle of 22.39 (11)° with respect to the attached benzene ring. In the crystal, mol-ecules assemble into double layers in the ab plane via C-H⋯O inter-actions.

Related literature

For the biological activity of indole derivatives, see: Okabe & Adachi (1998 ▶); Srivastava et al. (2011 ▶). For related structures, see: Chakkaravarthi et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C25H19ClN2O5S

M = 494.93

Triclinic,

a = 8.4658 (3) Å

b = 8.6643 (3) Å

c = 16.1126 (6) Å

α = 84.196 (2)°

β = 87.768 (3)°

γ = 79.541 (2)°

V = 1156.01 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 295 K

0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.922, T max = 0.943

25531 measured reflections

6333 independent reflections

4536 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.150

S = 1.03

6333 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.39 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 datablock(s) I, global. DOI: 10.1107/S1600536813031073/tk5271sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031073/tk5271Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031073/tk5271Isup3.cml

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

C25H19ClN2O5S	Z = 2
Mr = 494.93	F(000) = 512
Triclinic, P1	Dx = 1.422 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4658 (3) Å	Cell parameters from 8917 reflections
b = 8.6643 (3) Å	θ = 2.5–28.4°
c = 16.1126 (6) Å	µ = 0.30 mm−1
α = 84.196 (2)°	T = 295 K
β = 87.768 (3)°	Block, colourless
γ = 79.541 (2)°	0.28 × 0.24 × 0.20 mm
V = 1156.01 (7) Å3

Bruker Kappa APEXII diffractometer	6333 independent reflections
Radiation source: fine-focus sealed tube	4536 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω and φ scan	θmax = 29.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.922, Tmax = 0.943	k = −11→11
25531 measured reflections	l = −20→22

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0709P)2 + 0.3517P] where P = (Fo2 + 2Fc2)/3
6333 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.6620 (2)	0.1560 (2)	0.44142 (11)	0.0497 (4)
C2	0.7468 (3)	0.1501 (4)	0.51342 (14)	0.0765 (7)
H2	0.8570	0.1131	0.5140	0.092*
C3	0.6662 (4)	0.1997 (5)	0.58429 (16)	0.0984 (11)
H3	0.7215	0.1945	0.6336	0.118*
C4	0.5062 (4)	0.2564 (4)	0.58242 (17)	0.0920 (9)
H4	0.4537	0.2952	0.6298	0.110*
C5	0.4199 (4)	0.2573 (4)	0.51124 (19)	0.0991 (10)
H5	0.3093	0.2923	0.5115	0.119*
C6	0.4985 (3)	0.2060 (3)	0.43989 (15)	0.0781 (7)
H6	0.4420	0.2053	0.3916	0.094*
C7	0.6425 (2)	0.3393 (2)	0.23941 (10)	0.0408 (4)
C8	0.6569 (2)	0.4934 (2)	0.22907 (10)	0.0424 (4)
C9	0.7938 (2)	0.5131 (2)	0.27424 (11)	0.0439 (4)
C10	0.8617 (3)	0.6446 (2)	0.28430 (14)	0.0584 (5)
H10	0.8179	0.7435	0.2589	0.070*
C11	0.9950 (3)	0.6244 (3)	0.33266 (18)	0.0738 (7)
H11	1.0405	0.7113	0.3412	0.089*
C12	1.0626 (3)	0.4773 (3)	0.36883 (18)	0.0771 (7)
H12	1.1536	0.4675	0.4008	0.093*
C13	0.9999 (3)	0.3449 (3)	0.35916 (15)	0.0625 (5)
H13	1.0466	0.2461	0.3836	0.075*
C14	0.8635 (2)	0.3653 (2)	0.31128 (11)	0.0440 (4)
C15	0.5596 (2)	0.6261 (2)	0.17657 (12)	0.0516 (5)
C16	0.5615 (3)	0.6198 (3)	0.08490 (12)	0.0593 (5)
H16A	0.5066	0.5359	0.0729	0.071*
H16B	0.6722	0.5927	0.0657	0.071*
C17	0.4848 (4)	0.7702 (3)	0.03593 (16)	0.0880 (8)
H17A	0.3710	0.7884	0.0469	0.132*
H17B	0.5053	0.7613	−0.0226	0.132*
H17C	0.5291	0.8566	0.0523	0.132*
C18	0.5229 (2)	0.2611 (2)	0.20724 (10)	0.0442 (4)
H18	0.5563	0.1621	0.1884	0.053*
C19	0.3680 (2)	0.3249 (2)	0.20359 (11)	0.0467 (4)
H19	0.3352	0.4250	0.2212	0.056*
C20	0.2462 (2)	0.2449 (2)	0.17303 (11)	0.0453 (4)
C21	0.2582 (3)	0.0828 (2)	0.19095 (14)	0.0566 (5)
H21	0.3466	0.0271	0.2201	0.068*
C22	0.1449 (3)	0.0018 (2)	0.16730 (14)	0.0589 (5)
H22	0.1580	−0.1070	0.1796	0.071*
C23	0.0107 (2)	0.0832 (2)	0.12499 (12)	0.0518 (4)
C24	−0.0071 (2)	0.2427 (2)	0.10536 (12)	0.0487 (4)
H23	−0.0963	0.2976	0.0764	0.058*
C25	0.1097 (2)	0.3207 (2)	0.12932 (11)	0.0452 (4)
N1	0.77198 (17)	0.25460 (17)	0.28902 (9)	0.0427 (3)
N3	0.0859 (2)	0.4903 (2)	0.10290 (11)	0.0554 (4)
O1	0.6646 (2)	0.00599 (16)	0.31000 (9)	0.0651 (4)
O2	0.92318 (19)	0.02047 (18)	0.37066 (10)	0.0682 (4)
O3	0.4897 (3)	0.7364 (2)	0.20882 (12)	0.1283 (11)
O5	−0.04694 (18)	0.55877 (18)	0.08461 (11)	0.0692 (4)
O6	0.2012 (2)	0.5539 (2)	0.09605 (17)	0.1115 (9)
S1	0.76175 (6)	0.08992 (5)	0.35118 (3)	0.04869 (14)
Cl1	−0.13374 (7)	−0.01698 (7)	0.09611 (4)	0.07319 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0570 (11)	0.0502 (10)	0.0409 (9)	−0.0105 (8)	−0.0042 (8)	0.0040 (7)
C2	0.0641 (14)	0.121 (2)	0.0511 (12)	−0.0321 (14)	−0.0066 (10)	−0.0076 (13)
C3	0.098 (2)	0.169 (3)	0.0489 (13)	−0.071 (2)	0.0058 (13)	−0.0239 (17)
C4	0.114 (3)	0.112 (2)	0.0570 (15)	−0.0362 (19)	0.0260 (16)	−0.0210 (15)
C5	0.0807 (18)	0.127 (3)	0.0700 (17)	0.0174 (18)	0.0207 (14)	0.0128 (17)
C6	0.0669 (14)	0.106 (2)	0.0486 (12)	0.0085 (14)	−0.0037 (10)	0.0089 (12)
C7	0.0405 (8)	0.0465 (9)	0.0314 (7)	0.0034 (7)	−0.0039 (6)	−0.0038 (6)
C8	0.0444 (9)	0.0458 (9)	0.0330 (8)	0.0039 (7)	−0.0042 (7)	−0.0044 (7)
C9	0.0421 (9)	0.0493 (9)	0.0373 (8)	−0.0004 (7)	−0.0008 (7)	−0.0048 (7)
C10	0.0591 (12)	0.0499 (11)	0.0654 (13)	−0.0074 (9)	−0.0074 (10)	−0.0043 (9)
C11	0.0639 (14)	0.0660 (14)	0.0959 (18)	−0.0182 (11)	−0.0190 (13)	−0.0110 (13)
C12	0.0568 (13)	0.0819 (17)	0.0943 (19)	−0.0116 (12)	−0.0320 (13)	−0.0059 (14)
C13	0.0503 (11)	0.0655 (13)	0.0677 (13)	0.0003 (9)	−0.0196 (10)	0.0001 (10)
C14	0.0398 (8)	0.0495 (9)	0.0400 (9)	−0.0013 (7)	−0.0029 (7)	−0.0035 (7)
C15	0.0597 (11)	0.0460 (10)	0.0443 (10)	0.0046 (8)	−0.0140 (8)	−0.0024 (8)
C16	0.0538 (11)	0.0768 (14)	0.0393 (9)	0.0031 (10)	−0.0010 (8)	0.0057 (9)
C17	0.117 (2)	0.0850 (18)	0.0532 (13)	−0.0059 (16)	−0.0168 (14)	0.0213 (12)
C18	0.0476 (9)	0.0459 (9)	0.0369 (8)	−0.0009 (7)	−0.0060 (7)	−0.0045 (7)
C19	0.0471 (9)	0.0481 (10)	0.0424 (9)	−0.0022 (8)	−0.0022 (7)	−0.0042 (7)
C20	0.0412 (9)	0.0489 (10)	0.0430 (9)	−0.0024 (7)	0.0006 (7)	−0.0014 (7)
C21	0.0533 (11)	0.0505 (11)	0.0612 (12)	−0.0003 (9)	−0.0098 (9)	0.0045 (9)
C22	0.0625 (12)	0.0478 (10)	0.0644 (13)	−0.0080 (9)	−0.0033 (10)	0.0017 (9)
C23	0.0503 (10)	0.0574 (11)	0.0486 (10)	−0.0131 (9)	0.0045 (8)	−0.0052 (8)
C24	0.0388 (9)	0.0563 (11)	0.0482 (10)	−0.0044 (8)	0.0006 (7)	−0.0001 (8)
C25	0.0395 (9)	0.0479 (9)	0.0447 (9)	−0.0028 (7)	0.0035 (7)	0.0015 (7)
N1	0.0420 (7)	0.0436 (8)	0.0389 (7)	0.0004 (6)	−0.0064 (6)	0.0001 (6)
N3	0.0441 (8)	0.0534 (9)	0.0655 (10)	−0.0064 (7)	−0.0053 (7)	0.0068 (8)
O1	0.0916 (11)	0.0455 (7)	0.0589 (9)	−0.0115 (7)	−0.0143 (8)	−0.0052 (6)
O2	0.0624 (9)	0.0575 (8)	0.0722 (10)	0.0174 (7)	−0.0096 (7)	0.0063 (7)
O3	0.205 (3)	0.0840 (13)	0.0636 (11)	0.0794 (16)	−0.0502 (14)	−0.0264 (10)
O5	0.0509 (8)	0.0593 (9)	0.0903 (12)	0.0050 (7)	−0.0109 (8)	0.0038 (8)
O6	0.0654 (11)	0.0756 (12)	0.189 (2)	−0.0286 (9)	−0.0420 (13)	0.0514 (14)
S1	0.0554 (3)	0.0407 (2)	0.0451 (2)	0.00326 (19)	−0.00822 (19)	0.00039 (18)
Cl1	0.0676 (4)	0.0741 (4)	0.0840 (4)	−0.0276 (3)	−0.0047 (3)	−0.0088 (3)

C1—C6	1.374 (3)	C15—O3	1.185 (2)
C1—C2	1.380 (3)	C15—C16	1.483 (3)
C1—S1	1.747 (2)	C16—C17	1.506 (3)
C2—C3	1.373 (4)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.355 (5)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.383 (5)	C17—H17C	0.9600
C4—H4	0.9300	C18—C19	1.329 (3)
C5—C6	1.378 (4)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.468 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.355 (3)	C20—C21	1.391 (3)
C7—N1	1.427 (2)	C20—C25	1.399 (2)
C7—C18	1.454 (2)	C21—C22	1.373 (3)
C8—C9	1.437 (2)	C21—H21	0.9300
C8—C15	1.493 (2)	C22—C23	1.387 (3)
C9—C10	1.393 (3)	C22—H22	0.9300
C9—C14	1.394 (2)	C23—C24	1.369 (3)
C10—C11	1.371 (3)	C23—Cl1	1.725 (2)
C10—H10	0.9300	C24—C25	1.382 (3)
C11—C12	1.379 (4)	C24—H23	0.9300
C11—H11	0.9300	C25—N3	1.468 (2)
C12—C13	1.373 (3)	N1—S1	1.6720 (15)
C12—H12	0.9300	N3—O6	1.202 (2)
C13—C14	1.388 (3)	N3—O5	1.205 (2)
C13—H13	0.9300	O1—S1	1.4153 (16)
C14—N1	1.418 (2)	O2—S1	1.4230 (15)
C6—C1—C2	121.4 (2)	C17—C16—H16A	108.5
C6—C1—S1	118.79 (16)	C15—C16—H16B	108.5
C2—C1—S1	119.75 (18)	C17—C16—H16B	108.5
C3—C2—C1	119.1 (3)	H16A—C16—H16B	107.5
C3—C2—H2	120.5	C16—C17—H17A	109.5
C1—C2—H2	120.5	C16—C17—H17B	109.5
C4—C3—C2	120.0 (3)	H17A—C17—H17B	109.5
C4—C3—H3	120.0	C16—C17—H17C	109.5
C2—C3—H3	120.0	H17A—C17—H17C	109.5
C3—C4—C5	121.1 (3)	H17B—C17—H17C	109.5
C3—C4—H4	119.5	C19—C18—C7	122.80 (17)
C5—C4—H4	119.5	C19—C18—H18	118.6
C6—C5—C4	119.6 (3)	C7—C18—H18	118.6
C6—C5—H5	120.2	C18—C19—C20	123.04 (17)
C4—C5—H5	120.2	C18—C19—H19	118.5
C1—C6—C5	118.7 (2)	C20—C19—H19	118.5
C1—C6—H6	120.6	C21—C20—C25	115.37 (17)
C5—C6—H6	120.6	C21—C20—C19	119.73 (16)
C8—C7—N1	108.46 (15)	C25—C20—C19	124.82 (16)
C8—C7—C18	129.63 (15)	C22—C21—C20	122.68 (18)
N1—C7—C18	121.90 (15)	C22—C21—H21	118.7
C7—C8—C9	108.69 (15)	C20—C21—H21	118.7
C7—C8—C15	128.84 (16)	C21—C22—C23	119.55 (19)
C9—C8—C15	122.37 (17)	C21—C22—H22	120.2
C10—C9—C14	119.98 (17)	C23—C22—H22	120.2
C10—C9—C8	132.32 (17)	C24—C23—C22	120.32 (19)
C14—C9—C8	107.70 (16)	C24—C23—Cl1	119.70 (16)
C11—C10—C9	118.2 (2)	C22—C23—Cl1	119.98 (16)
C11—C10—H10	120.9	C23—C24—C25	118.76 (17)
C9—C10—H10	120.9	C23—C24—H23	120.6
C10—C11—C12	121.1 (2)	C25—C24—H23	120.6
C10—C11—H11	119.5	C24—C25—C20	123.31 (17)
C12—C11—H11	119.5	C24—C25—N3	115.63 (15)
C13—C12—C11	122.2 (2)	C20—C25—N3	121.01 (16)
C13—C12—H12	118.9	C14—N1—C7	107.57 (13)
C11—C12—H12	118.9	C14—N1—S1	120.91 (11)
C12—C13—C14	116.9 (2)	C7—N1—S1	123.89 (12)
C12—C13—H13	121.5	O6—N3—O5	122.39 (18)
C14—C13—H13	121.5	O6—N3—C25	118.61 (16)
C13—C14—C9	121.65 (19)	O5—N3—C25	118.88 (16)
C13—C14—N1	130.80 (18)	O1—S1—O2	120.22 (10)
C9—C14—N1	107.55 (14)	O1—S1—N1	106.22 (8)
O3—C15—C16	122.04 (18)	O2—S1—N1	106.01 (9)
O3—C15—C8	119.14 (17)	O1—S1—C1	109.63 (10)
C16—C15—C8	118.71 (16)	O2—S1—C1	109.04 (10)
C15—C16—C17	114.9 (2)	N1—S1—C1	104.52 (8)
C15—C16—H16A	108.5
C6—C1—C2—C3	−1.9 (4)	C25—C20—C21—C22	0.3 (3)
S1—C1—C2—C3	−178.8 (2)	C19—C20—C21—C22	177.18 (19)
C1—C2—C3—C4	−1.3 (5)	C20—C21—C22—C23	−1.1 (3)
C2—C3—C4—C5	3.6 (5)	C21—C22—C23—C24	1.4 (3)
C3—C4—C5—C6	−2.7 (5)	C21—C22—C23—Cl1	−179.18 (17)
C2—C1—C6—C5	2.7 (4)	C22—C23—C24—C25	−0.7 (3)
S1—C1—C6—C5	179.7 (2)	Cl1—C23—C24—C25	179.79 (14)
C4—C5—C6—C1	−0.4 (5)	C23—C24—C25—C20	−0.1 (3)
N1—C7—C8—C9	−1.87 (19)	C23—C24—C25—N3	177.42 (17)
C18—C7—C8—C9	179.19 (17)	C21—C20—C25—C24	0.4 (3)
N1—C7—C8—C15	174.39 (17)	C19—C20—C25—C24	−176.37 (17)
C18—C7—C8—C15	−4.6 (3)	C21—C20—C25—N3	−177.05 (18)
C7—C8—C9—C10	179.8 (2)	C19—C20—C25—N3	6.2 (3)
C15—C8—C9—C10	3.2 (3)	C13—C14—N1—C7	179.4 (2)
C7—C8—C9—C14	0.9 (2)	C9—C14—N1—C7	−1.50 (18)
C15—C8—C9—C14	−175.62 (16)	C13—C14—N1—S1	28.8 (3)
C14—C9—C10—C11	−1.5 (3)	C9—C14—N1—S1	−152.11 (13)
C8—C9—C10—C11	179.8 (2)	C8—C7—N1—C14	2.11 (19)
C9—C10—C11—C12	1.6 (4)	C18—C7—N1—C14	−178.85 (15)
C10—C11—C12—C13	−0.7 (4)	C8—C7—N1—S1	151.63 (13)
C11—C12—C13—C14	−0.3 (4)	C18—C7—N1—S1	−29.3 (2)
C12—C13—C14—C9	0.4 (3)	C24—C25—N3—O6	−155.4 (2)
C12—C13—C14—N1	179.3 (2)	C20—C25—N3—O6	22.2 (3)
C10—C9—C14—C13	0.5 (3)	C24—C25—N3—O5	20.7 (3)
C8—C9—C14—C13	179.57 (18)	C20—C25—N3—O5	−161.72 (19)
C10—C9—C14—N1	−178.64 (17)	C14—N1—S1—O1	−178.89 (13)
C8—C9—C14—N1	0.39 (19)	C7—N1—S1—O1	35.43 (16)
C7—C8—C15—O3	121.1 (3)	C14—N1—S1—O2	−49.93 (15)
C9—C8—C15—O3	−63.1 (3)	C7—N1—S1—O2	164.38 (14)
C7—C8—C15—C16	−62.5 (3)	C14—N1—S1—C1	65.22 (15)
C9—C8—C15—C16	113.3 (2)	C7—N1—S1—C1	−80.47 (15)
O3—C15—C16—C17	6.7 (4)	C6—C1—S1—O1	−37.0 (2)
C8—C15—C16—C17	−169.6 (2)	C2—C1—S1—O1	139.98 (19)
C8—C7—C18—C19	−39.8 (3)	C6—C1—S1—O2	−170.50 (19)
N1—C7—C18—C19	141.39 (18)	C2—C1—S1—O2	6.5 (2)
C7—C18—C19—C20	−178.51 (16)	C6—C1—S1—N1	76.5 (2)
C18—C19—C20—C21	37.1 (3)	C2—C1—S1—N1	−106.5 (2)
C18—C19—C20—C25	−146.33 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1i	0.93	2.60	3.327 (3)	136
C16—H16B···O5ii	0.97	2.37	3.260 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O1i	0.93	2.60	3.327 (3)	136
C16—H16B⋯O5ii	0.97	2.37	3.260 (3)	152

Symmetry codes: (i) ; (ii) .