Crystal structure of 3-(2-nitro-phen-yl)-1-(1-phenyl-sulfonyl-1H-indol-3-yl)propan-1-one.

In the title compound, C23H18N2O5S, the phenyl and benzene rings subtend dihedral angles of 78.18 (10) and 30.18 (9)°, respectively, with the indole ring system (r.m.s. deviation = 0.022 Å). The crystal structure features weak C-H⋯O and C-H⋯π inter-actions, which link the mol-ecules into a three-dimensional network.

Related literature

For the biological activity of indole derivatives, see: Andreev et al. (2015 ▸); Kolocouris et al. (1994 ▸). For related structures, see: Chakkaravarthi et al. (2007 ▸, 2008 ▸).

Experimental

Crystal data

C23H18N2O5S

M = 434.45

Monoclinic,

a = 9.0224 (7) Å

b = 15.4581 (10) Å

c = 15.1347 (10) Å

β = 106.349 (2)°

V = 2025.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 295 K

0.26 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.950, T max = 0.961

29555 measured reflections

6149 independent reflections

4060 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.144

S = 1.09

6149 reflections

280 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.32 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 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015020162/hb7524sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020162/hb7524Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020162/hb7524Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015020162/hb7524fig1.tif

The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015020162/hb7524fig2.tif

The crystal packing of the title compound, viewed along the a axis. The C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1). H atoms not involved in these inter­actions have been omitted for clarity.

CCDC reference: 1433093

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

C23H18N2O5S	F(000) = 904
Mr = 434.45	Dx = 1.425 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7714 reflections
a = 9.0224 (7) Å	θ = 2.4–28.3°
b = 15.4581 (10) Å	µ = 0.20 mm−1
c = 15.1347 (10) Å	T = 295 K
β = 106.349 (2)°	Block, colourless
V = 2025.5 (2) Å3	0.26 × 0.24 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	6149 independent reflections
Radiation source: fine-focus sealed tube	4060 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scan	θmax = 31.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.950, Tmax = 0.961	k = −21→22
29555 measured reflections	l = −21→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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.048P)2 + 1.0896P] where P = (Fo2 + 2Fc2)/3
6149 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.35 e Å−3
3 restraints	Δρmin = −0.32 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.7579 (2)	−0.01858 (14)	0.38658 (13)	0.0384 (4)
C2	0.6908 (3)	−0.05928 (17)	0.44691 (16)	0.0514 (6)
H2	0.6403	−0.1120	0.4318	0.062*
C3	0.7005 (3)	−0.0197 (2)	0.53057 (17)	0.0663 (8)
H3	0.6565	−0.0460	0.5724	0.080*
C4	0.7746 (3)	0.0580 (2)	0.55179 (18)	0.0690 (8)
H4	0.7801	0.0842	0.6079	0.083*
C5	0.8408 (3)	0.09752 (19)	0.49126 (18)	0.0655 (7)
H5	0.8907	0.1504	0.5065	0.079*
C6	0.8337 (3)	0.05935 (16)	0.40815 (16)	0.0527 (6)
H6	0.8793	0.0857	0.3671	0.063*
C7	0.4643 (2)	−0.01056 (13)	0.18344 (12)	0.0327 (4)
C8	0.3702 (2)	−0.05590 (14)	0.22590 (14)	0.0400 (5)
H8	0.4111	−0.0932	0.2749	0.048*
C9	0.2134 (2)	−0.04298 (15)	0.19192 (15)	0.0445 (5)
H9	0.1467	−0.0715	0.2191	0.053*
C10	0.1528 (2)	0.01177 (15)	0.11793 (15)	0.0445 (5)
H10	0.0463	0.0184	0.0961	0.053*
C11	0.2462 (2)	0.05662 (13)	0.07591 (14)	0.0390 (4)
H11	0.2039	0.0927	0.0260	0.047*
C12	0.4060 (2)	0.04658 (12)	0.11020 (12)	0.0314 (4)
C13	0.5371 (2)	0.08392 (13)	0.08696 (13)	0.0330 (4)
C14	0.6664 (2)	0.04867 (13)	0.14399 (13)	0.0349 (4)
H14	0.7669	0.0618	0.1438	0.042*
C15	0.5289 (2)	0.15065 (14)	0.01681 (14)	0.0407 (5)
C16	0.6745 (2)	0.17783 (14)	−0.00516 (13)	0.0365 (4)
H16A	0.7236	0.1273	−0.0225	0.044*
H16B	0.7453	0.2027	0.0494	0.044*
C17	0.6424 (2)	0.24371 (14)	−0.08307 (13)	0.0375 (4)
H17A	0.5508	0.2259	−0.1306	0.045*
H17B	0.6201	0.2991	−0.0596	0.045*
C18	0.7729 (2)	0.25523 (12)	−0.12581 (12)	0.0331 (4)
C19	0.7489 (2)	0.27562 (13)	−0.21829 (13)	0.0375 (4)
C20	0.8658 (3)	0.27853 (15)	−0.26069 (16)	0.0512 (6)
H20	0.8433	0.2895	−0.3235	0.061*
C21	1.0150 (3)	0.26509 (17)	−0.2093 (2)	0.0612 (7)
H21	1.0954	0.2681	−0.2364	0.073*
C22	1.0444 (3)	0.24708 (17)	−0.11702 (19)	0.0583 (7)
H22	1.1457	0.2387	−0.0814	0.070*
C23	0.9255 (2)	0.24134 (15)	−0.07669 (15)	0.0452 (5)
H23	0.9485	0.2277	−0.0144	0.054*
N1	0.62637 (18)	−0.00978 (11)	0.20252 (11)	0.0368 (4)
N2	0.5930 (2)	0.29460 (14)	−0.27675 (13)	0.0504 (4)
O1	0.68799 (19)	−0.15240 (10)	0.28042 (12)	0.0548 (4)
O2	0.89596 (16)	−0.05570 (11)	0.26200 (11)	0.0528 (4)
O3	0.40514 (19)	0.18257 (14)	−0.02227 (16)	0.0843 (7)
O4	0.5110 (2)	0.34181 (14)	−0.24777 (13)	0.0738 (6)
O5	0.5554 (2)	0.26312 (16)	−0.35371 (12)	0.0846 (7)
S1	0.75288 (6)	−0.06854 (4)	0.28195 (4)	0.04012 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0297 (10)	0.0474 (12)	0.0366 (10)	0.0047 (8)	0.0069 (8)	0.0104 (9)
C2	0.0462 (13)	0.0614 (15)	0.0479 (13)	−0.0007 (11)	0.0153 (10)	0.0164 (11)
C3	0.0641 (17)	0.094 (2)	0.0461 (13)	0.0018 (16)	0.0239 (12)	0.0168 (14)
C4	0.0702 (18)	0.092 (2)	0.0437 (13)	0.0085 (16)	0.0135 (12)	−0.0041 (14)
C5	0.0732 (18)	0.0651 (17)	0.0550 (15)	−0.0096 (14)	0.0130 (13)	−0.0070 (13)
C6	0.0536 (14)	0.0578 (15)	0.0476 (13)	−0.0061 (11)	0.0155 (11)	0.0091 (11)
C7	0.0253 (9)	0.0404 (10)	0.0338 (9)	−0.0015 (7)	0.0106 (7)	−0.0059 (8)
C8	0.0353 (10)	0.0500 (12)	0.0379 (10)	−0.0038 (9)	0.0153 (8)	0.0015 (9)
C9	0.0327 (10)	0.0569 (13)	0.0499 (12)	−0.0094 (9)	0.0217 (9)	−0.0047 (10)
C10	0.0249 (9)	0.0551 (13)	0.0551 (12)	−0.0025 (9)	0.0137 (9)	−0.0089 (11)
C11	0.0297 (10)	0.0428 (11)	0.0431 (11)	0.0032 (8)	0.0078 (8)	−0.0022 (9)
C12	0.0278 (9)	0.0348 (9)	0.0327 (9)	−0.0012 (7)	0.0104 (7)	−0.0058 (7)
C13	0.0285 (9)	0.0379 (10)	0.0345 (9)	−0.0014 (7)	0.0118 (7)	−0.0030 (8)
C14	0.0262 (9)	0.0450 (11)	0.0356 (9)	−0.0024 (8)	0.0121 (7)	0.0008 (8)
C15	0.0320 (10)	0.0450 (11)	0.0458 (11)	0.0016 (9)	0.0121 (8)	0.0065 (9)
C16	0.0304 (10)	0.0447 (11)	0.0333 (9)	−0.0010 (8)	0.0071 (7)	0.0069 (8)
C17	0.0341 (10)	0.0439 (11)	0.0341 (10)	0.0030 (8)	0.0088 (8)	0.0061 (8)
C18	0.0316 (9)	0.0346 (9)	0.0312 (9)	−0.0012 (8)	0.0057 (7)	0.0035 (7)
C19	0.0391 (9)	0.0370 (10)	0.0352 (9)	0.0011 (8)	0.0084 (7)	0.0092 (8)
C20	0.0593 (15)	0.0524 (13)	0.0483 (12)	0.0049 (11)	0.0258 (11)	0.0171 (10)
C21	0.0493 (14)	0.0625 (16)	0.0833 (19)	0.0094 (12)	0.0377 (13)	0.0260 (14)
C22	0.0299 (11)	0.0644 (16)	0.0780 (17)	0.0042 (10)	0.0108 (11)	0.0224 (13)
C23	0.0353 (11)	0.0550 (13)	0.0400 (11)	−0.0012 (9)	0.0020 (8)	0.0097 (10)
N1	0.0247 (7)	0.0512 (10)	0.0353 (8)	−0.0006 (7)	0.0096 (6)	0.0061 (7)
N2	0.0463 (9)	0.0630 (12)	0.0374 (10)	0.0006 (8)	0.0042 (7)	0.0201 (9)
O1	0.0543 (10)	0.0441 (9)	0.0673 (11)	0.0027 (7)	0.0192 (8)	0.0051 (8)
O2	0.0296 (8)	0.0740 (11)	0.0580 (9)	0.0098 (7)	0.0173 (7)	0.0095 (8)
O3	0.0350 (9)	0.1001 (16)	0.1185 (17)	0.0172 (9)	0.0228 (10)	0.0669 (14)
O4	0.0556 (11)	0.0885 (14)	0.0741 (13)	0.0308 (9)	0.0130 (9)	0.0299 (10)
O5	0.0781 (14)	0.1281 (19)	0.0350 (9)	−0.0157 (13)	−0.0045 (9)	0.0106 (11)
S1	0.0301 (2)	0.0473 (3)	0.0443 (3)	0.0062 (2)	0.0126 (2)	0.0080 (2)

C1—C6	1.378 (3)	C14—N1	1.383 (2)
C1—C2	1.381 (3)	C14—H14	0.9300
C1—S1	1.751 (2)	C15—O3	1.212 (3)
C2—C3	1.387 (4)	C15—C16	1.502 (3)
C2—H2	0.9300	C16—C17	1.523 (3)
C3—C4	1.367 (4)	C16—H16A	0.9700
C3—H3	0.9300	C16—H16B	0.9700
C4—C5	1.370 (4)	C17—C18	1.505 (3)
C4—H4	0.9300	C17—H17A	0.9700
C5—C6	1.374 (3)	C17—H17B	0.9700
C5—H5	0.9300	C18—C23	1.385 (3)
C6—H6	0.9300	C18—C19	1.391 (3)
C7—C8	1.391 (3)	C19—C20	1.381 (3)
C7—C12	1.399 (3)	C19—N2	1.465 (3)
C7—N1	1.408 (2)	C20—C21	1.368 (4)
C8—C9	1.377 (3)	C20—H20	0.9300
C8—H8	0.9300	C21—C22	1.375 (4)
C9—C10	1.387 (3)	C21—H21	0.9300
C9—H9	0.9300	C22—C23	1.379 (3)
C10—C11	1.377 (3)	C22—H22	0.9300
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.397 (3)	N1—S1	1.6736 (17)
C11—H11	0.9300	N2—O4	1.207 (3)
C12—C13	1.445 (2)	N2—O5	1.219 (3)
C13—C14	1.355 (3)	O1—S1	1.4199 (17)
C13—C15	1.467 (3)	O2—S1	1.4200 (15)
C6—C1—C2	121.5 (2)	C13—C15—C16	119.20 (17)
C6—C1—S1	118.98 (16)	C15—C16—C17	111.76 (16)
C2—C1—S1	119.51 (18)	C15—C16—H16A	109.3
C1—C2—C3	118.4 (2)	C17—C16—H16A	109.3
C1—C2—H2	120.8	C15—C16—H16B	109.3
C3—C2—H2	120.8	C17—C16—H16B	109.3
C4—C3—C2	120.2 (2)	H16A—C16—H16B	107.9
C4—C3—H3	119.9	C18—C17—C16	114.23 (16)
C2—C3—H3	119.9	C18—C17—H17A	108.7
C3—C4—C5	120.7 (3)	C16—C17—H17A	108.7
C3—C4—H4	119.6	C18—C17—H17B	108.7
C5—C4—H4	119.6	C16—C17—H17B	108.7
C4—C5—C6	120.2 (3)	H17A—C17—H17B	107.6
C4—C5—H5	119.9	C23—C18—C19	115.16 (18)
C6—C5—H5	119.9	C23—C18—C17	122.06 (17)
C5—C6—C1	119.0 (2)	C19—C18—C17	122.69 (17)
C5—C6—H6	120.5	C20—C19—C18	123.49 (19)
C1—C6—H6	120.5	C20—C19—N2	116.22 (18)
C8—C7—C12	122.82 (17)	C18—C19—N2	120.29 (18)
C8—C7—N1	130.07 (18)	C21—C20—C19	119.3 (2)
C12—C7—N1	107.11 (16)	C21—C20—H20	120.4
C9—C8—C7	116.8 (2)	C19—C20—H20	120.4
C9—C8—H8	121.6	C20—C21—C22	119.1 (2)
C7—C8—H8	121.6	C20—C21—H21	120.4
C8—C9—C10	121.31 (19)	C22—C21—H21	120.4
C8—C9—H9	119.3	C21—C22—C23	120.7 (2)
C10—C9—H9	119.3	C21—C22—H22	119.6
C11—C10—C9	121.80 (19)	C23—C22—H22	119.6
C11—C10—H10	119.1	C22—C23—C18	122.2 (2)
C9—C10—H10	119.1	C22—C23—H23	118.9
C10—C11—C12	118.3 (2)	C18—C23—H23	118.9
C10—C11—H11	120.8	C14—N1—C7	108.51 (15)
C12—C11—H11	120.8	C14—N1—S1	124.51 (13)
C11—C12—C7	118.88 (17)	C7—N1—S1	126.97 (13)
C11—C12—C13	134.02 (18)	O4—N2—O5	123.7 (2)
C7—C12—C13	107.10 (16)	O4—N2—C19	119.0 (2)
C14—C13—C12	107.52 (17)	O5—N2—C19	117.3 (2)
C14—C13—C15	127.04 (17)	O1—S1—O2	121.30 (10)
C12—C13—C15	125.39 (17)	O1—S1—N1	106.80 (9)
C13—C14—N1	109.73 (16)	O2—S1—N1	104.39 (9)
C13—C14—H14	125.1	O1—S1—C1	108.84 (10)
N1—C14—H14	125.1	O2—S1—C1	109.71 (10)
O3—C15—C13	119.40 (19)	N1—S1—C1	104.41 (9)
O3—C15—C16	121.40 (19)
C6—C1—C2—C3	0.3 (3)	C23—C18—C19—C20	2.7 (3)
S1—C1—C2—C3	178.00 (18)	C17—C18—C19—C20	−173.8 (2)
C1—C2—C3—C4	0.2 (4)	C23—C18—C19—N2	−177.95 (19)
C2—C3—C4—C5	−0.3 (4)	C17—C18—C19—N2	5.6 (3)
C3—C4—C5—C6	−0.1 (4)	C18—C19—C20—C21	−3.4 (4)
C4—C5—C6—C1	0.6 (4)	N2—C19—C20—C21	177.3 (2)
C2—C1—C6—C5	−0.7 (3)	C19—C20—C21—C22	1.4 (4)
S1—C1—C6—C5	−178.44 (19)	C20—C21—C22—C23	0.9 (4)
C12—C7—C8—C9	0.6 (3)	C21—C22—C23—C18	−1.5 (4)
N1—C7—C8—C9	179.64 (19)	C19—C18—C23—C22	−0.2 (3)
C7—C8—C9—C10	0.9 (3)	C17—C18—C23—C22	176.3 (2)
C8—C9—C10—C11	−1.0 (3)	C13—C14—N1—C7	−1.3 (2)
C9—C10—C11—C12	−0.6 (3)	C13—C14—N1—S1	178.71 (14)
C10—C11—C12—C7	2.1 (3)	C8—C7—N1—C14	−177.3 (2)
C10—C11—C12—C13	−177.6 (2)	C12—C7—N1—C14	1.8 (2)
C8—C7—C12—C11	−2.2 (3)	C8—C7—N1—S1	2.6 (3)
N1—C7—C12—C11	178.61 (17)	C12—C7—N1—S1	−178.24 (14)
C8—C7—C12—C13	177.62 (18)	C20—C19—N2—O4	−135.8 (2)
N1—C7—C12—C13	−1.6 (2)	C18—C19—N2—O4	44.9 (3)
C11—C12—C13—C14	−179.4 (2)	C20—C19—N2—O5	42.3 (3)
C7—C12—C13—C14	0.8 (2)	C18—C19—N2—O5	−137.1 (2)
C11—C12—C13—C15	3.0 (3)	C14—N1—S1—O1	−139.88 (17)
C7—C12—C13—C15	−176.77 (18)	C7—N1—S1—O1	40.16 (19)
C12—C13—C14—N1	0.3 (2)	C14—N1—S1—O2	−10.27 (19)
C15—C13—C14—N1	177.84 (19)	C7—N1—S1—O2	169.78 (17)
C14—C13—C15—O3	−172.1 (2)	C14—N1—S1—C1	104.91 (17)
C12—C13—C15—O3	5.0 (3)	C7—N1—S1—C1	−75.05 (18)
C14—C13—C15—C16	8.0 (3)	C6—C1—S1—O1	172.14 (17)
C12—C13—C15—C16	−174.90 (18)	C2—C1—S1—O1	−5.6 (2)
O3—C15—C16—C17	−3.1 (3)	C6—C1—S1—O2	37.3 (2)
C13—C15—C16—C17	176.79 (18)	C2—C1—S1—O2	−140.47 (17)
C15—C16—C17—C18	−164.04 (17)	C6—C1—S1—N1	−74.09 (18)
C16—C17—C18—C23	−28.2 (3)	C2—C1—S1—N1	108.15 (18)
C16—C17—C18—C19	148.00 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2i	0.93	2.54	3.328 (2)	143
C22—H22···O3ii	0.93	2.42	3.319 (3)	163
C23—H23···O5iii	0.93	2.36	3.247 (3)	160
C16—H16A···Cg3iv	0.97	2.73	3.565 (2)	144

Table 1

Hydrogen-bond geometry (, )

Cg3 is the centroid of the C7C12 ring.

DHA	DH	HA	D A	DHA
C9H9O2i	0.93	2.54	3.328(2)	143
C22H22O3ii	0.93	2.42	3.319(3)	163
C23H23O5iii	0.93	2.36	3.247(3)	160
C16H16A Cg3iv	0.97	2.73	3.565(2)	144

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