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

In the title compound, C25H19FN2O5S, the substituted phenyl ring makes a dihedral angle of 12.26 (9)° with the indole ring system. The nitro group is twisted at an angle of 26.92 (8)° out of the plane of the ring to which it is attached. The mol-ecular structure is stabilized by weak C-H⋯O hydrogen bonds. In the crystal, weak C-H⋯O, C-H⋯F and π-π [centroid-centroid distance = 3.6645 (11) Å] inter-actions link the mol-ecules, forming a three-dimensional network.

Related literature

For the biological activity of indole derivatives, see: Pomarnacka & Kozlarska-Kedra (2003 ▶); Srivastava et al. (2011 ▶). For related structures, see: Chakkaravarthi et al. (2008 ▶, 2010 ▶). For details of the configuration at the S atom, see: Bassindale (1984 ▶). For details of N-atom hybridization, see: Beddoes et al. (1986 ▶).

Experimental

Crystal data

C25H19FN2O5S

M = 478.48

Triclinic,

a = 8.2615 (3) Å

b = 10.7624 (5) Å

c = 13.2432 (6) Å

α = 68.606 (2)°

β = 80.554 (3)°

γ = 81.012 (2)°

V = 1075.53 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 295 K

0.30 × 0.24 × 0.20 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.942, T max = 0.961

27388 measured reflections

8185 independent reflections

5506 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.176

S = 1.03

8185 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.96 e Å−3

Δρmin = −0.61 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/S1600536813030961/bt6945sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030961/bt6945Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030961/bt6945Isup3.cml

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

C25H19FN2O5S	Z = 2
Mr = 478.48	F(000) = 496
Triclinic, P1	Dx = 1.477 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2615 (3) Å	Cell parameters from 5619 reflections
b = 10.7624 (5) Å	θ = 2.1–31.1°
c = 13.2432 (6) Å	µ = 0.20 mm−1
α = 68.606 (2)°	T = 295 K
β = 80.554 (3)°	Block, colourless
γ = 81.012 (2)°	0.30 × 0.24 × 0.20 mm
V = 1075.53 (8) Å3

Bruker APEXII diffractometer	8185 independent reflections
Radiation source: fine-focus sealed tube	5506 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scan	θmax = 35.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.942, Tmax = 0.961	k = −16→17
27388 measured reflections	l = −20→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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.089P)2 + 0.2703P] where P = (Fo2 + 2Fc2)/3
8185 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.96 e Å−3
0 restraints	Δρmin = −0.61 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	−0.05337 (18)	0.17906 (15)	0.76350 (12)	0.0387 (3)
C2	−0.0663 (2)	0.06833 (18)	0.85866 (14)	0.0476 (4)
H2	0.0275	0.0203	0.8901	0.057*
C3	−0.2214 (2)	0.0306 (2)	0.90598 (16)	0.0563 (4)
H3	−0.2324	−0.0430	0.9702	0.068*
C4	−0.3602 (2)	0.1021 (2)	0.85825 (16)	0.0540 (4)
H4	−0.4641	0.0762	0.8907	0.065*
C5	−0.3457 (2)	0.2109 (2)	0.76326 (16)	0.0548 (4)
H5	−0.4397	0.2576	0.7314	0.066*
C6	−0.1920 (2)	0.25156 (19)	0.71465 (14)	0.0489 (4)
H6	−0.1817	0.3257	0.6507	0.059*
C7	0.1475 (2)	0.19323 (17)	0.50807 (12)	0.0439 (3)
C8	0.0691 (3)	0.3166 (2)	0.44803 (15)	0.0596 (5)
H8	0.0385	0.3851	0.4765	0.072*
C9	0.0389 (3)	0.3323 (2)	0.34425 (16)	0.0668 (6)
H9	−0.0130	0.4135	0.3020	0.080*
C10	0.0836 (3)	0.2308 (2)	0.30181 (15)	0.0637 (5)
H10	0.0627	0.2457	0.2312	0.076*
C11	0.1583 (2)	0.1080 (2)	0.36119 (13)	0.0544 (4)
H11	0.1858	0.0397	0.3322	0.065*
C12	0.1919 (2)	0.08841 (17)	0.46722 (12)	0.0429 (3)
C13	0.27195 (19)	−0.02364 (15)	0.54893 (12)	0.0403 (3)
C14	0.27322 (18)	0.01380 (14)	0.63737 (11)	0.0367 (3)
C15	0.3524 (3)	−0.14616 (18)	0.52664 (14)	0.0522 (4)
C16	0.4209 (3)	−0.26746 (18)	0.61156 (15)	0.0563 (4)
H16A	0.3365	−0.2957	0.6730	0.068*
H16B	0.5119	−0.2449	0.6373	0.068*
C17	0.4816 (4)	−0.3835 (2)	0.5708 (2)	0.0767 (7)
H17A	0.3896	−0.4137	0.5537	0.115*
H17B	0.5345	−0.4558	0.6265	0.115*
H17C	0.5589	−0.3542	0.5065	0.115*
C18	0.34816 (19)	−0.05675 (15)	0.73895 (11)	0.0380 (3)
H18	0.4365	−0.0220	0.7510	0.046*
C19	0.29602 (19)	−0.16804 (15)	0.81477 (11)	0.0380 (3)
H19	0.2011	−0.1976	0.8059	0.046*
C20	0.37971 (18)	−0.24690 (14)	0.91153 (11)	0.0360 (3)
C21	0.5492 (2)	−0.24341 (16)	0.90850 (14)	0.0454 (3)
H21	0.6053	−0.1874	0.8457	0.054*
C22	0.6361 (2)	−0.31934 (18)	0.99463 (15)	0.0510 (4)
H22	0.7478	−0.3125	0.9913	0.061*
C23	0.5542 (2)	−0.40558 (17)	1.08570 (15)	0.0511 (4)
C24	0.3899 (2)	−0.41643 (16)	1.09468 (13)	0.0462 (4)
H24	0.3370	−0.4760	1.1569	0.055*
C25	0.30441 (19)	−0.33571 (15)	1.00810 (11)	0.0384 (3)
N1	0.20107 (17)	0.14790 (13)	0.61298 (10)	0.0410 (3)
N2	0.12683 (19)	−0.34714 (16)	1.02366 (11)	0.0489 (3)
O1	0.12824 (18)	0.36656 (12)	0.64011 (11)	0.0580 (3)
O2	0.25410 (15)	0.17470 (13)	0.78405 (10)	0.0492 (3)
O3	0.3708 (3)	−0.1422 (2)	0.43278 (14)	0.1065 (8)
O4	0.03576 (17)	−0.25160 (16)	0.97436 (13)	0.0684 (4)
O5	0.0783 (2)	−0.45267 (19)	1.08539 (15)	0.0913 (6)
S1	0.14288 (5)	0.22764 (4)	0.70332 (3)	0.04104 (11)
F1	0.64046 (18)	−0.48260 (14)	1.16881 (11)	0.0778 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0383 (7)	0.0433 (7)	0.0372 (7)	−0.0005 (5)	−0.0030 (5)	−0.0194 (6)
C2	0.0446 (8)	0.0492 (9)	0.0453 (8)	−0.0023 (6)	−0.0044 (6)	−0.0135 (7)
C3	0.0536 (10)	0.0562 (10)	0.0553 (10)	−0.0114 (8)	0.0045 (8)	−0.0171 (8)
C4	0.0426 (8)	0.0676 (11)	0.0620 (11)	−0.0103 (8)	0.0031 (7)	−0.0366 (9)
C5	0.0401 (8)	0.0756 (12)	0.0585 (10)	0.0042 (8)	−0.0096 (7)	−0.0372 (10)
C6	0.0465 (9)	0.0570 (10)	0.0430 (8)	0.0034 (7)	−0.0073 (6)	−0.0199 (7)
C7	0.0439 (8)	0.0475 (8)	0.0315 (6)	−0.0027 (6)	−0.0015 (6)	−0.0055 (6)
C8	0.0646 (11)	0.0569 (11)	0.0416 (9)	0.0094 (9)	−0.0054 (8)	−0.0053 (8)
C9	0.0628 (12)	0.0732 (13)	0.0416 (9)	0.0056 (10)	−0.0100 (8)	0.0033 (9)
C10	0.0587 (11)	0.0875 (15)	0.0335 (8)	−0.0111 (10)	−0.0098 (7)	−0.0047 (9)
C11	0.0584 (10)	0.0704 (12)	0.0337 (7)	−0.0154 (9)	−0.0069 (7)	−0.0131 (7)
C12	0.0430 (8)	0.0509 (8)	0.0304 (6)	−0.0113 (6)	−0.0013 (5)	−0.0078 (6)
C13	0.0456 (8)	0.0412 (7)	0.0322 (6)	−0.0095 (6)	−0.0010 (5)	−0.0100 (5)
C14	0.0390 (7)	0.0370 (7)	0.0303 (6)	−0.0049 (5)	−0.0004 (5)	−0.0082 (5)
C15	0.0694 (11)	0.0485 (9)	0.0438 (8)	−0.0094 (8)	−0.0045 (8)	−0.0216 (7)
C16	0.0739 (12)	0.0455 (9)	0.0468 (9)	0.0002 (8)	0.0042 (8)	−0.0202 (7)
C17	0.1053 (19)	0.0522 (11)	0.0682 (13)	−0.0006 (11)	0.0154 (13)	−0.0298 (10)
C18	0.0422 (7)	0.0379 (7)	0.0326 (6)	−0.0020 (5)	−0.0038 (5)	−0.0118 (5)
C19	0.0397 (7)	0.0407 (7)	0.0315 (6)	−0.0033 (5)	−0.0026 (5)	−0.0110 (5)
C20	0.0412 (7)	0.0340 (6)	0.0318 (6)	−0.0024 (5)	−0.0033 (5)	−0.0116 (5)
C21	0.0423 (8)	0.0421 (8)	0.0453 (8)	−0.0035 (6)	−0.0041 (6)	−0.0085 (6)
C22	0.0444 (8)	0.0480 (9)	0.0570 (10)	−0.0009 (7)	−0.0135 (7)	−0.0127 (7)
C23	0.0628 (11)	0.0431 (8)	0.0458 (8)	0.0028 (7)	−0.0217 (8)	−0.0105 (7)
C24	0.0606 (10)	0.0419 (8)	0.0334 (7)	−0.0055 (7)	−0.0074 (6)	−0.0089 (6)
C25	0.0460 (8)	0.0367 (7)	0.0322 (6)	−0.0055 (5)	−0.0031 (5)	−0.0119 (5)
N1	0.0473 (7)	0.0399 (6)	0.0302 (5)	0.0019 (5)	−0.0018 (5)	−0.0093 (5)
N2	0.0490 (8)	0.0547 (8)	0.0382 (7)	−0.0129 (6)	0.0003 (6)	−0.0096 (6)
O1	0.0655 (8)	0.0389 (6)	0.0634 (8)	−0.0044 (5)	0.0000 (6)	−0.0142 (6)
O2	0.0431 (6)	0.0580 (7)	0.0523 (7)	−0.0025 (5)	−0.0092 (5)	−0.0258 (6)
O3	0.187 (2)	0.0818 (12)	0.0574 (9)	0.0227 (13)	−0.0319 (12)	−0.0396 (9)
O4	0.0455 (7)	0.0704 (9)	0.0690 (9)	−0.0035 (6)	−0.0025 (6)	−0.0031 (7)
O5	0.0707 (10)	0.0820 (11)	0.0877 (12)	−0.0339 (9)	−0.0065 (9)	0.0192 (9)
S1	0.0421 (2)	0.03958 (19)	0.0412 (2)	−0.00283 (14)	−0.00230 (14)	−0.01553 (15)
F1	0.0838 (9)	0.0747 (8)	0.0621 (7)	−0.0007 (7)	−0.0385 (7)	0.0009 (6)

C1—C2	1.385 (2)	C15—O3	1.213 (2)
C1—C6	1.391 (2)	C15—C16	1.482 (3)
C1—S1	1.7532 (16)	C16—C17	1.520 (3)
C2—C3	1.383 (3)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.383 (3)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.374 (3)	C17—H17C	0.9600
C4—H4	0.9300	C18—C19	1.330 (2)
C5—C6	1.385 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.4678 (19)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.394 (2)	C20—C21	1.401 (2)
C7—C12	1.397 (2)	C20—C25	1.403 (2)
C7—N1	1.4155 (19)	C21—C22	1.375 (2)
C8—C9	1.382 (3)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.373 (3)
C9—C10	1.379 (3)	C22—H22	0.9300
C9—H9	0.9300	C23—F1	1.3465 (19)
C10—C11	1.375 (3)	C23—C24	1.363 (3)
C10—H10	0.9300	C24—C25	1.384 (2)
C11—C12	1.410 (2)	C24—H24	0.9300
C11—H11	0.9300	C25—N2	1.466 (2)
C12—C13	1.448 (2)	N1—S1	1.6824 (13)
C13—C14	1.373 (2)	N2—O5	1.215 (2)
C13—C15	1.488 (2)	N2—O4	1.216 (2)
C14—N1	1.4131 (19)	O1—S1	1.4193 (13)
C14—C18	1.467 (2)	O2—S1	1.4235 (13)
C2—C1—C6	121.56 (16)	C17—C16—H16A	109.0
C2—C1—S1	118.92 (12)	C15—C16—H16B	109.0
C6—C1—S1	119.52 (13)	C17—C16—H16B	109.0
C3—C2—C1	118.70 (16)	H16A—C16—H16B	107.8
C3—C2—H2	120.7	C16—C17—H17A	109.5
C1—C2—H2	120.7	C16—C17—H17B	109.5
C2—C3—C4	120.28 (18)	H17A—C17—H17B	109.5
C2—C3—H3	119.9	C16—C17—H17C	109.5
C4—C3—H3	119.9	H17A—C17—H17C	109.5
C5—C4—C3	120.48 (17)	H17B—C17—H17C	109.5
C5—C4—H4	119.8	C19—C18—C14	123.25 (14)
C3—C4—H4	119.8	C19—C18—H18	118.4
C4—C5—C6	120.46 (17)	C14—C18—H18	118.4
C4—C5—H5	119.8	C18—C19—C20	123.78 (14)
C6—C5—H5	119.8	C18—C19—H19	118.1
C5—C6—C1	118.52 (17)	C20—C19—H19	118.1
C5—C6—H6	120.7	C21—C20—C25	115.36 (14)
C1—C6—H6	120.7	C21—C20—C19	119.86 (13)
C8—C7—C12	122.28 (16)	C25—C20—C19	124.64 (14)
C8—C7—N1	130.77 (17)	C22—C21—C20	122.68 (15)
C12—C7—N1	106.93 (13)	C22—C21—H21	118.7
C9—C8—C7	117.0 (2)	C20—C21—H21	118.7
C9—C8—H8	121.5	C23—C22—C21	118.50 (17)
C7—C8—H8	121.5	C23—C22—H22	120.8
C10—C9—C8	121.67 (19)	C21—C22—H22	120.8
C10—C9—H9	119.2	F1—C23—C24	119.04 (17)
C8—C9—H9	119.2	F1—C23—C22	118.45 (17)
C11—C10—C9	121.72 (18)	C24—C23—C22	122.51 (16)
C11—C10—H10	119.1	C23—C24—C25	117.75 (15)
C9—C10—H10	119.1	C23—C24—H24	121.1
C10—C11—C12	118.23 (19)	C25—C24—H24	121.1
C10—C11—H11	120.9	C24—C25—C20	123.15 (15)
C12—C11—H11	120.9	C24—C25—N2	115.60 (14)
C7—C12—C11	119.09 (16)	C20—C25—N2	121.24 (13)
C7—C12—C13	108.19 (13)	C14—N1—C7	108.72 (12)
C11—C12—C13	132.70 (17)	C14—N1—S1	125.70 (10)
C14—C13—C12	107.60 (14)	C7—N1—S1	123.84 (11)
C14—C13—C15	129.90 (15)	O5—N2—O4	123.33 (17)
C12—C13—C15	122.08 (14)	O5—N2—C25	117.83 (16)
C13—C14—N1	108.51 (13)	O4—N2—C25	118.84 (14)
C13—C14—C18	130.55 (14)	O1—S1—O2	120.42 (8)
N1—C14—C18	120.63 (13)	O1—S1—N1	105.64 (7)
O3—C15—C16	119.04 (18)	O2—S1—N1	106.91 (7)
O3—C15—C13	117.57 (18)	O1—S1—C1	109.25 (8)
C16—C15—C13	123.24 (14)	O2—S1—C1	108.80 (7)
C15—C16—C17	113.04 (17)	N1—S1—C1	104.66 (7)
C15—C16—H16A	109.0
C6—C1—C2—C3	−0.6 (3)	C25—C20—C21—C22	−1.3 (2)
S1—C1—C2—C3	179.82 (14)	C19—C20—C21—C22	−177.11 (15)
C1—C2—C3—C4	0.5 (3)	C20—C21—C22—C23	2.4 (3)
C2—C3—C4—C5	0.2 (3)	C21—C22—C23—F1	178.20 (16)
C3—C4—C5—C6	−0.7 (3)	C21—C22—C23—C24	−1.5 (3)
C4—C5—C6—C1	0.6 (3)	F1—C23—C24—C25	179.81 (15)
C2—C1—C6—C5	0.0 (2)	C22—C23—C24—C25	−0.5 (3)
S1—C1—C6—C5	179.63 (13)	C23—C24—C25—C20	1.7 (2)
C12—C7—C8—C9	−1.0 (3)	C23—C24—C25—N2	−177.55 (15)
N1—C7—C8—C9	177.10 (18)	C21—C20—C25—C24	−0.8 (2)
C7—C8—C9—C10	0.2 (3)	C19—C20—C25—C24	174.77 (14)
C8—C9—C10—C11	1.0 (3)	C21—C20—C25—N2	178.40 (14)
C9—C10—C11—C12	−1.3 (3)	C19—C20—C25—N2	−6.0 (2)
C8—C7—C12—C11	0.7 (3)	C13—C14—N1—C7	2.37 (17)
N1—C7—C12—C11	−177.79 (14)	C18—C14—N1—C7	176.59 (13)
C8—C7—C12—C13	179.31 (17)	C13—C14—N1—S1	167.73 (11)
N1—C7—C12—C13	0.79 (17)	C18—C14—N1—S1	−18.1 (2)
C10—C11—C12—C7	0.4 (3)	C8—C7—N1—C14	179.72 (18)
C10—C11—C12—C13	−177.72 (17)	C12—C7—N1—C14	−1.92 (17)
C7—C12—C13—C14	0.66 (17)	C8—C7—N1—S1	14.0 (3)
C11—C12—C13—C14	178.97 (17)	C12—C7—N1—S1	−167.62 (11)
C7—C12—C13—C15	−172.65 (15)	C24—C25—N2—O5	−27.0 (2)
C11—C12—C13—C15	5.7 (3)	C20—C25—N2—O5	153.67 (18)
C12—C13—C14—N1	−1.84 (16)	C24—C25—N2—O4	153.21 (16)
C15—C13—C14—N1	170.76 (16)	C20—C25—N2—O4	−26.1 (2)
C12—C13—C14—C18	−175.29 (15)	C14—N1—S1—O1	161.77 (13)
C15—C13—C14—C18	−2.7 (3)	C7—N1—S1—O1	−34.98 (15)
C14—C13—C15—O3	−161.0 (2)	C14—N1—S1—O2	32.38 (15)
C12—C13—C15—O3	10.7 (3)	C7—N1—S1—O2	−164.37 (13)
C14—C13—C15—C16	14.4 (3)	C14—N1—S1—C1	−82.94 (14)
C12—C13—C15—C16	−173.90 (17)	C7—N1—S1—C1	80.31 (14)
O3—C15—C16—C17	−10.1 (3)	C2—C1—S1—O1	−154.93 (13)
C13—C15—C16—C17	174.49 (19)	C6—C1—S1—O1	25.46 (15)
C13—C14—C18—C19	−67.9 (2)	C2—C1—S1—O2	−21.66 (15)
N1—C14—C18—C19	119.31 (17)	C6—C1—S1—O2	158.73 (12)
C14—C18—C19—C20	173.75 (13)	C2—C1—S1—N1	92.33 (13)
C18—C19—C20—C21	−26.3 (2)	C6—C1—S1—N1	−87.28 (13)
C18—C19—C20—C25	158.25 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.33	2.913 (3)	120
C11—H11···O3	0.93	2.40	2.905 (3)	114
C16—H16A···F1i	0.97	2.54	3.192 (2)	124
C22—H22···O4ii	0.93	2.52	3.438 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.93	2.33	2.913 (3)	120
C11—H11⋯O3	0.93	2.40	2.905 (3)	114
C16—H16A⋯F1i	0.97	2.54	3.192 (2)	124
C22—H22⋯O4ii	0.93	2.52	3.438 (2)	170

Symmetry codes: (i) ; (ii) .