(E)-2-Bromo-1-[2-(2-nitro-styr-yl)-1-phenyl-sulfonyl-1H-indol-3-yl]ethanone.

In the title compound C24H17BrN2O5S, the phenyl ring makes dihedral angles of 85.4 (2) and 8.8 (2)° with the indole ring system and the nitro-benzene ring, respectively, while the indole ring system and nitrobenzene ring make a dihedral angle of 80.1 (2)°. In the crystal, weak C-H⋯O inter-actions link the mol-ecules, forming a two-dimensional network parallel to the bc plane.

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001 ▶); Singh et al. (2000 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶); Srivastava & Pandeya (2011 ▶). For a related structure, see: Umadevi et al. (2013 ▶); Kanchanadevi et al. (2013 ▶).

Experimental

Crystal data

C24H17BrN2O5S

M = 525.37

Monoclinic,

a = 10.1823 (7) Å

b = 8.0932 (6) Å

c = 13.8111 (12) Å

β = 102.749 (2)°

V = 1110.08 (15) Å3

Z = 2

Mo Kα radiation

μ = 1.99 mm−1

T = 295 K

0.35 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.543, T max = 0.609

17011 measured reflections

4323 independent reflections

3368 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.116

S = 1.01

4323 reflections

298 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.43 e Å−3

Absolute structure: Flack (1983 ▶), 2093 Friedel pairs

Absolute structure parameter: 0.022 (9)

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/S1600536814000488/hg5374sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000488/hg5374Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000488/hg5374Isup3.cml

CCDC reference:

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

C24H17BrN2O5S	F(000) = 532
Mr = 525.37	Dx = 1.572 Mg m−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 4350 reflections
a = 10.1823 (7) Å	θ = 2.3–26.3°
b = 8.0932 (6) Å	µ = 1.99 mm−1
c = 13.8111 (12) Å	T = 295 K
β = 102.749 (2)°	Block, yellow
V = 1110.08 (15) Å3	0.35 × 0.25 × 0.25 mm
Z = 2

Bruker APEXII CCD diffractometer	4323 independent reflections
Radiation source: fine-focus sealed tube	3368 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 0 pixels mm-1	θmax = 26.3°, θmin = 2.3°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.543, Tmax = 0.609	l = −17→17
17011 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.3412P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
4323 reflections	Δρmax = 0.85 e Å−3
298 parameters	Δρmin = −0.43 e Å−3
2 restraints	Absolute structure: Flack (1983), 2093 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.022 (9)

	x	y	z	Uiso*/Ueq
C1	0.0805 (4)	0.3950 (5)	0.3857 (3)	0.0358 (8)
C2	0.0594 (5)	0.5284 (5)	0.3192 (3)	0.0516 (11)
H2	−0.0157	0.5329	0.2669	0.062*
C3	0.1535 (5)	0.6512 (5)	0.3345 (4)	0.0556 (11)
H3	0.1419	0.7411	0.2915	0.067*
C4	0.2643 (5)	0.6461 (5)	0.4112 (3)	0.0516 (11)
H4	0.3264	0.7319	0.4184	0.062*
C5	0.2867 (5)	0.5171 (5)	0.4783 (3)	0.0437 (10)
H5	0.3617	0.5156	0.5309	0.052*
C6	0.1926 (4)	0.3890 (4)	0.4643 (3)	0.0327 (8)
C7	0.1862 (4)	0.2356 (4)	0.5157 (3)	0.0307 (7)
C8	0.0699 (4)	0.1549 (4)	0.4711 (3)	0.0332 (8)
C9	0.0184 (4)	0.0034 (4)	0.5039 (3)	0.0353 (8)
H9	−0.0185	−0.0765	0.4574	0.042*
C10	0.0230 (4)	−0.0236 (4)	0.5997 (3)	0.0340 (8)
H10	0.0499	0.0638	0.6432	0.041*
C11	−0.0110 (3)	−0.1803 (5)	0.6424 (3)	0.0330 (8)
C12	0.0184 (4)	−0.3288 (4)	0.6024 (3)	0.0366 (9)
H12	0.0557	−0.3276	0.5467	0.044*
C13	−0.0058 (4)	−0.4776 (5)	0.6424 (3)	0.0445 (10)
H13	0.0152	−0.5753	0.6138	0.053*
C14	−0.0612 (5)	−0.4832 (5)	0.7250 (4)	0.0483 (11)
H14	−0.0772	−0.5844	0.7522	0.058*
C15	−0.0924 (4)	−0.3399 (5)	0.7662 (3)	0.0462 (10)
H15	−0.1307	−0.3427	0.8214	0.055*
C16	−0.0671 (4)	−0.1910 (5)	0.7261 (3)	0.0391 (9)
C17	−0.2379 (4)	0.3680 (6)	0.4081 (3)	0.0478 (11)
C18	−0.2824 (5)	0.3030 (7)	0.4874 (4)	0.0632 (13)
H18	−0.2719	0.1908	0.5016	0.076*
C19	−0.3424 (6)	0.4035 (10)	0.5456 (5)	0.0866 (19)
H19	−0.3735	0.3600	0.5987	0.104*
C20	−0.3552 (5)	0.5662 (10)	0.5243 (6)	0.088 (2)
H20	−0.3955	0.6344	0.5636	0.106*
C21	−0.3106 (6)	0.6341 (8)	0.4465 (6)	0.086 (2)
H21	−0.3205	0.7468	0.4339	0.103*
C22	−0.2511 (5)	0.5356 (6)	0.3871 (5)	0.0660 (14)
H22	−0.2204	0.5803	0.3341	0.079*
C23	0.2995 (4)	0.1765 (5)	0.5939 (3)	0.0380 (8)
C24	0.3438 (5)	−0.0005 (5)	0.5889 (4)	0.0540 (12)
H24A	0.3226	−0.0366	0.5203	0.065*
H24B	0.2936	−0.0696	0.6254	0.065*
N1	0.0045 (3)	0.2503 (4)	0.3896 (2)	0.0356 (7)
N2	−0.1036 (5)	−0.0428 (5)	0.7741 (3)	0.0598 (11)
O1	−0.1734 (3)	0.3120 (5)	0.2399 (2)	0.0654 (9)
O2	−0.2013 (3)	0.0745 (4)	0.3449 (2)	0.0602 (9)
O3	−0.1280 (5)	0.0831 (5)	0.7280 (4)	0.1015 (17)
O4	−0.1194 (10)	−0.0537 (6)	0.8566 (4)	0.171 (4)
O5	0.3599 (4)	0.2701 (4)	0.6549 (3)	0.0840 (13)
S1	−0.16138 (10)	0.24019 (13)	0.33528 (8)	0.0465 (3)
Br1	0.53169 (7)	−0.02967 (7)	0.64210 (6)	0.0930 (3)

	U11	U22	U33	U12	U13	U23
C1	0.041 (2)	0.0338 (19)	0.0347 (19)	0.0033 (16)	0.0131 (16)	0.0055 (16)
C2	0.068 (3)	0.046 (2)	0.041 (2)	0.009 (2)	0.012 (2)	0.0114 (19)
C3	0.078 (3)	0.035 (2)	0.063 (3)	0.005 (2)	0.035 (3)	0.015 (2)
C4	0.072 (3)	0.031 (2)	0.064 (3)	−0.0046 (19)	0.040 (3)	−0.0004 (19)
C5	0.048 (2)	0.039 (2)	0.050 (2)	0.0000 (17)	0.0229 (19)	−0.0033 (18)
C6	0.0388 (19)	0.0250 (18)	0.037 (2)	0.0017 (15)	0.0154 (16)	−0.0031 (16)
C7	0.0379 (19)	0.0241 (18)	0.0314 (18)	0.0009 (15)	0.0103 (15)	−0.0018 (14)
C8	0.0386 (19)	0.0281 (19)	0.0337 (18)	0.0002 (15)	0.0094 (15)	−0.0067 (15)
C9	0.038 (2)	0.028 (2)	0.039 (2)	−0.0018 (15)	0.0053 (16)	−0.0013 (15)
C10	0.0364 (19)	0.0233 (17)	0.043 (2)	0.0005 (15)	0.0108 (17)	−0.0048 (15)
C11	0.0287 (17)	0.033 (2)	0.038 (2)	−0.0034 (14)	0.0090 (16)	0.0015 (16)
C12	0.0358 (19)	0.033 (2)	0.044 (2)	0.0006 (16)	0.0136 (17)	−0.0053 (16)
C13	0.050 (3)	0.029 (2)	0.057 (3)	0.0020 (16)	0.017 (2)	−0.0053 (19)
C14	0.057 (3)	0.031 (2)	0.059 (3)	−0.0047 (18)	0.016 (2)	0.0098 (19)
C15	0.052 (2)	0.043 (2)	0.049 (2)	0.000 (2)	0.0239 (19)	0.008 (2)
C16	0.045 (2)	0.0307 (19)	0.044 (2)	0.0013 (17)	0.0143 (18)	−0.0052 (17)
C17	0.032 (2)	0.050 (3)	0.057 (3)	−0.0010 (17)	0.0001 (19)	−0.008 (2)
C18	0.052 (3)	0.069 (3)	0.069 (3)	0.001 (2)	0.015 (2)	−0.012 (3)
C19	0.059 (3)	0.102 (5)	0.105 (5)	−0.008 (3)	0.032 (3)	−0.036 (4)
C20	0.042 (3)	0.101 (6)	0.123 (6)	0.002 (3)	0.021 (3)	−0.049 (4)
C21	0.056 (3)	0.064 (4)	0.128 (6)	0.010 (3)	0.001 (4)	−0.033 (4)
C22	0.045 (3)	0.055 (3)	0.092 (4)	0.008 (2)	0.004 (3)	−0.009 (3)
C23	0.045 (2)	0.030 (2)	0.035 (2)	−0.0002 (17)	0.0018 (17)	−0.0032 (16)
C24	0.057 (3)	0.039 (2)	0.056 (3)	0.0065 (19)	−0.009 (2)	0.001 (2)
N1	0.0380 (16)	0.0322 (16)	0.0351 (16)	0.0039 (13)	0.0050 (13)	0.0071 (13)
N2	0.090 (3)	0.039 (2)	0.060 (3)	0.0112 (19)	0.038 (2)	−0.0005 (19)
O1	0.072 (2)	0.073 (2)	0.0417 (17)	0.0108 (18)	−0.0076 (15)	0.0061 (15)
O2	0.0532 (18)	0.0504 (19)	0.068 (2)	−0.0068 (14)	−0.0050 (16)	−0.0124 (15)
O3	0.160 (5)	0.047 (2)	0.127 (4)	0.025 (2)	0.097 (4)	0.008 (2)
O4	0.381 (12)	0.081 (3)	0.095 (4)	0.049 (5)	0.149 (6)	0.003 (3)
O5	0.090 (3)	0.051 (2)	0.084 (3)	0.0122 (18)	−0.037 (2)	−0.0277 (19)
S1	0.0421 (5)	0.0469 (6)	0.0439 (5)	0.0024 (5)	−0.0046 (4)	−0.0057 (5)
Br1	0.0538 (3)	0.0647 (3)	0.1580 (7)	0.0143 (3)	0.0183 (3)	−0.0032 (4)

C1—C6	1.392 (5)	C14—H14	0.9300
C1—C2	1.403 (6)	C15—C16	1.374 (6)
C1—N1	1.412 (5)	C15—H15	0.9300
C2—C3	1.364 (7)	C16—N2	1.457 (5)
C2—H2	0.9300	C17—C18	1.379 (7)
C3—C4	1.368 (7)	C17—C22	1.387 (7)
C3—H3	0.9300	C17—S1	1.742 (4)
C4—C5	1.381 (6)	C18—C19	1.378 (8)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.396 (6)	C19—C20	1.349 (11)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.439 (5)	C20—C21	1.370 (10)
C7—C8	1.373 (5)	C20—H20	0.9300
C7—C23	1.475 (5)	C21—C22	1.378 (8)
C8—N1	1.406 (5)	C21—H21	0.9300
C8—C9	1.445 (5)	C22—H22	0.9300
C9—C10	1.332 (5)	C23—O5	1.197 (5)
C9—H9	0.9300	C23—C24	1.508 (5)
C10—C11	1.472 (5)	C24—Br1	1.907 (5)
C10—H10	0.9300	C24—H24A	0.9700
C11—C12	1.383 (5)	C24—H24B	0.9700
C11—C16	1.400 (5)	N1—S1	1.692 (3)
C12—C13	1.370 (5)	N2—O4	1.188 (6)
C12—H12	0.9300	N2—O3	1.198 (5)
C13—C14	1.380 (6)	O1—S1	1.420 (3)
C13—H13	0.9300	O2—S1	1.416 (3)
C14—C15	1.361 (6)
C6—C1—C2	121.2 (4)	C16—C15—H15	120.1
C6—C1—N1	107.7 (3)	C15—C16—C11	122.3 (3)
C2—C1—N1	131.1 (4)	C15—C16—N2	116.7 (4)
C3—C2—C1	117.3 (4)	C11—C16—N2	121.1 (3)
C3—C2—H2	121.3	C18—C17—C22	120.4 (5)
C1—C2—H2	121.3	C18—C17—S1	119.9 (4)
C2—C3—C4	121.9 (4)	C22—C17—S1	119.6 (4)
C2—C3—H3	119.0	C19—C18—C17	120.3 (6)
C4—C3—H3	119.0	C19—C18—H18	119.9
C3—C4—C5	121.9 (4)	C17—C18—H18	119.9
C3—C4—H4	119.0	C20—C19—C18	118.8 (7)
C5—C4—H4	119.0	C20—C19—H19	120.6
C4—C5—C6	117.5 (4)	C18—C19—H19	120.6
C4—C5—H5	121.3	C19—C20—C21	122.0 (6)
C6—C5—H5	121.3	C19—C20—H20	119.0
C1—C6—C5	120.1 (4)	C21—C20—H20	119.0
C1—C6—C7	107.2 (3)	C20—C21—C22	120.0 (6)
C5—C6—C7	132.6 (4)	C20—C21—H21	120.0
C8—C7—C6	108.5 (3)	C22—C21—H21	120.0
C8—C7—C23	129.2 (3)	C21—C22—C17	118.4 (6)
C6—C7—C23	121.8 (3)	C21—C22—H22	120.8
C7—C8—N1	107.9 (3)	C17—C22—H22	120.8
C7—C8—C9	126.8 (3)	O5—C23—C7	120.4 (4)
N1—C8—C9	125.2 (3)	O5—C23—C24	121.4 (4)
C10—C9—C8	121.0 (3)	C7—C23—C24	117.9 (3)
C10—C9—H9	119.5	C23—C24—Br1	112.6 (3)
C8—C9—H9	119.5	C23—C24—H24A	109.1
C9—C10—C11	125.5 (3)	Br1—C24—H24A	109.1
C9—C10—H10	117.3	C23—C24—H24B	109.1
C11—C10—H10	117.3	Br1—C24—H24B	109.1
C12—C11—C16	116.1 (3)	H24A—C24—H24B	107.8
C12—C11—C10	119.8 (3)	C8—N1—C1	108.6 (3)
C16—C11—C10	124.0 (3)	C8—N1—S1	125.4 (2)
C13—C12—C11	121.9 (4)	C1—N1—S1	121.7 (2)
C13—C12—H12	119.0	O4—N2—O3	121.1 (4)
C11—C12—H12	119.0	O4—N2—C16	118.5 (4)
C12—C13—C14	120.3 (4)	O3—N2—C16	120.1 (4)
C12—C13—H13	119.8	O2—S1—O1	120.4 (2)
C14—C13—H13	119.8	O2—S1—N1	106.46 (17)
C15—C14—C13	119.6 (4)	O1—S1—N1	105.34 (19)
C15—C14—H14	120.2	O2—S1—C17	109.5 (2)
C13—C14—H14	120.2	O1—S1—C17	109.5 (2)
C14—C15—C16	119.8 (4)	N1—S1—C17	104.24 (17)
C14—C15—H15	120.1
C6—C1—C2—C3	0.4 (6)	C17—C18—C19—C20	−0.8 (8)
N1—C1—C2—C3	−179.1 (4)	C18—C19—C20—C21	0.1 (9)
C1—C2—C3—C4	0.0 (7)	C19—C20—C21—C22	0.3 (9)
C2—C3—C4—C5	−0.7 (7)	C20—C21—C22—C17	0.0 (8)
C3—C4—C5—C6	1.0 (6)	C18—C17—C22—C21	−0.7 (7)
C2—C1—C6—C5	0.0 (6)	S1—C17—C22—C21	−179.3 (4)
N1—C1—C6—C5	179.6 (3)	C8—C7—C23—O5	−146.1 (4)
C2—C1—C6—C7	−178.3 (4)	C6—C7—C23—O5	42.6 (6)
N1—C1—C6—C7	1.3 (4)	C8—C7—C23—C24	39.2 (6)
C4—C5—C6—C1	−0.7 (5)	C6—C7—C23—C24	−132.1 (4)
C4—C5—C6—C7	177.1 (4)	O5—C23—C24—Br1	−25.8 (6)
C1—C6—C7—C8	−2.4 (4)	C7—C23—C24—Br1	148.9 (3)
C5—C6—C7—C8	179.6 (4)	C7—C8—N1—C1	−1.6 (4)
C1—C6—C7—C23	170.6 (3)	C9—C8—N1—C1	175.4 (3)
C5—C6—C7—C23	−7.4 (6)	C7—C8—N1—S1	−158.3 (3)
C6—C7—C8—N1	2.4 (4)	C9—C8—N1—S1	18.7 (5)
C23—C7—C8—N1	−169.8 (4)	C6—C1—N1—C8	0.2 (4)
C6—C7—C8—C9	−174.6 (3)	C2—C1—N1—C8	179.7 (4)
C23—C7—C8—C9	13.2 (6)	C6—C1—N1—S1	157.9 (2)
C7—C8—C9—C10	41.5 (6)	C2—C1—N1—S1	−22.6 (6)
N1—C8—C9—C10	−135.1 (4)	C15—C16—N2—O4	19.0 (8)
C8—C9—C10—C11	−172.1 (4)	C11—C16—N2—O4	−162.0 (7)
C9—C10—C11—C12	34.8 (6)	C15—C16—N2—O3	−154.8 (5)
C9—C10—C11—C16	−148.3 (4)	C11—C16—N2—O3	24.3 (7)
C16—C11—C12—C13	−0.1 (5)	C8—N1—S1—O2	−32.0 (3)
C10—C11—C12—C13	177.0 (4)	C1—N1—S1—O2	174.2 (3)
C11—C12—C13—C14	0.1 (6)	C8—N1—S1—O1	−160.9 (3)
C12—C13—C14—C15	0.3 (7)	C1—N1—S1—O1	45.2 (3)
C13—C14—C15—C16	−0.7 (7)	C8—N1—S1—C17	83.8 (3)
C14—C15—C16—C11	0.8 (6)	C1—N1—S1—C17	−70.1 (3)
C14—C15—C16—N2	179.8 (4)	C18—C17—S1—O2	22.6 (4)
C12—C11—C16—C15	−0.3 (6)	C22—C17—S1—O2	−158.8 (3)
C10—C11—C16—C15	−177.3 (4)	C18—C17—S1—O1	156.7 (4)
C12—C11—C16—N2	−179.4 (4)	C22—C17—S1—O1	−24.7 (4)
C10—C11—C16—N2	3.7 (6)	C18—C17—S1—N1	−91.0 (4)
C22—C17—C18—C19	1.1 (7)	C22—C17—S1—N1	87.6 (4)
S1—C17—C18—C19	179.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5i	0.93	2.38	3.147 (5)	139
C2—H2···O1	0.93	2.38	2.957 (6)	120
C9—H9···O2	0.93	2.47	2.827 (5)	103
C10—H10···O3	0.93	2.37	2.730 (5)	103

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5i	0.93	2.38	3.147 (5)	139

Symmetry code: (i) .