Literature DB >> 24765002

2-Bromo-1-(1-phenyl-sulfonyl-1H-indol-3-yl)propan-1-one.

C Ramathilagam¹, P R Umarani², V Saravanan³, A K Mohanakrishnan³, B Gunasekaran⁴, V Manivannan⁵.

Abstract

In the title compound, C17H14BrNO3S, the phenyl ring makes a dihedral angle of 89.78 (16)° with the plane of the indole ring system. The terminal Br atom and the methyl group are disordered over two sets of sites, with site occupancies of 0.860 (2) and 0.140 (2). In the crystal, mol-ecules are linked into a chain along the b-axis direction by weak C-H⋯O hydrogen bonds. The chains are further linked by C-H⋯π inter-actions, forming layers parallel to the bc plane.

Entities: Chemical Disease Species

Year: 2014 PMID： 24765002 PMCID： PMC3998462 DOI： 10.1107/S1600536814002864

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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 related structures, see: Umadevi et al. (2013 ▶); Kanchanadevi et al. (2014 ▶).

Experimental

Crystal data

C17H14BrNO3S M = 392.26 Monoclinic, a = 8.7539 (3) Å b = 10.9968 (4) Å c = 17.5801 (7) Å β = 99.231 (2)° V = 1670.43 (11) Å3 Z = 4 Mo Kα radiation μ = 2.60 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 = 0.416, T max = 0.522 15009 measured reflections 4141 independent reflections 2334 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.149 S = 1.03 4141 reflections 222 parameters 5 restraints H-atom parameters constrained Δρmax = 0.41 e Å−3 Δρmin = −0.51 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT (Bruker, 2008 ▶); 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 (Sheldrick, 2008 ▶). Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814002864/is5339sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002864/is5339Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814002864/is5339Isup3.cml CCDC reference: 985849 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₇H₁₄BrNO₃S	F(000) = 792
M_r = 392.26	D_x = 1.560 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4350 reflections
a = 8.7539 (3) Å	θ = 2.2–28.4°
b = 10.9968 (4) Å	µ = 2.60 mm⁻¹
c = 17.5801 (7) Å	T = 295 K
β = 99.231 (2)°	Block, yellow
V = 1670.43 (11) Å³	0.35 × 0.25 × 0.25 mm
Z = 4

Bruker APEXII CCD diffractometer	4141 independent reflections
Radiation source: fine-focus sealed tube	2334 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 0 pixels mm^-1	θ_max = 28.5°, θ_min = 2.2°
ω and φ scans	h = −11→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→14
T_min = 0.416, T_max = 0.522	l = −21→23
15009 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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.0673P)² + 0.7073P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4141 reflections	Δρ_max = 0.41 e Å⁻³
222 parameters	Δρ_min = −0.51 e Å⁻³
5 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (9)

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.7170 (3)	0.2542 (3)	0.30787 (16)	0.0382 (7)
C2	0.6804 (4)	0.1348 (3)	0.28691 (18)	0.0480 (8)
H2	0.7480	0.0850	0.2655	0.058*
C3	0.5365 (4)	0.0944 (3)	0.2998 (2)	0.0558 (9)
H3	0.5071	0.0148	0.2870	0.067*
C4	0.4359 (4)	0.1688 (3)	0.3310 (2)	0.0627 (10)
H4	0.3398	0.1387	0.3380	0.075*
C5	0.4753 (4)	0.2878 (3)	0.3522 (2)	0.0552 (9)
H5	0.4072	0.3373	0.3735	0.066*
C6	0.6184 (3)	0.3308 (3)	0.34090 (16)	0.0392 (7)
C7	0.6963 (3)	0.4468 (2)	0.35599 (16)	0.0391 (7)
C8	0.8349 (3)	0.4370 (2)	0.33195 (16)	0.0375 (7)
H8	0.9074	0.4992	0.3341	0.045*
C9	0.8963 (3)	0.3192 (3)	0.15480 (17)	0.0427 (7)
C10	0.9085 (4)	0.4343 (3)	0.12403 (19)	0.0587 (9)
H10	0.9658	0.4947	0.1527	0.070*
C11	0.8349 (5)	0.4573 (4)	0.0508 (2)	0.0803 (12)
H11	0.8417	0.5339	0.0292	0.096*
C12	0.7501 (5)	0.3665 (4)	0.0088 (2)	0.0820 (13)
H12	0.6992	0.3830	−0.0407	0.098*
C13	0.7405 (5)	0.2530 (4)	0.0393 (2)	0.0804 (13)
H13	0.6845	0.1926	0.0101	0.096*
C14	0.8121 (4)	0.2279 (3)	0.1120 (2)	0.0614 (9)
H14	0.8050	0.1508	0.1329	0.074*
C15	0.6362 (4)	0.5538 (3)	0.39046 (19)	0.0511 (8)
C16	0.7409 (4)	0.6635 (2)	0.40341 (9)	0.0651 (10)
H16A	0.8186	0.6547	0.3694	0.078*	0.860 (2)
H16B	0.7916	0.6656	0.3576	0.078*	0.140 (2)
Br1	0.84813 (7)	0.65595 (6)	0.50680 (4)	0.0973 (3)	0.860 (2)
C17	0.6681 (10)	0.7883 (4)	0.3880 (5)	0.0539 (15)	0.860 (2)
H17A	0.7036	0.8411	0.4307	0.081*	0.860 (2)
H17B	0.5575	0.7812	0.3817	0.081*	0.860 (2)
H17C	0.6973	0.8215	0.3419	0.081*	0.860 (2)
Br1A	0.6298 (11)	0.8071 (6)	0.3977 (7)	0.132 (4)	0.140 (2)
C17A	0.875 (2)	0.6591 (18)	0.4701 (12)	0.0539 (15)	0.140 (2)
H17D	0.9557	0.7124	0.4596	0.081*	0.140 (2)
H17E	0.9138	0.5775	0.4763	0.081*	0.140 (2)
H17F	0.8396	0.6846	0.5166	0.081*	0.140 (2)
N1	0.8539 (3)	0.3213 (2)	0.30363 (13)	0.0384 (6)
O1	1.0168 (3)	0.16368 (19)	0.25653 (14)	0.0591 (6)
O2	1.1079 (2)	0.3760 (2)	0.27067 (13)	0.0526 (6)
O3	0.5058 (3)	0.5548 (2)	0.40600 (18)	0.0778 (8)
S1	0.98775 (9)	0.29060 (7)	0.24862 (4)	0.0422 (2)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0438 (16)	0.0389 (15)	0.0298 (16)	0.0014 (13)	−0.0003 (12)	0.0057 (12)
C2	0.059 (2)	0.0392 (17)	0.0421 (19)	−0.0028 (14)	−0.0019 (15)	0.0011 (13)
C3	0.060 (2)	0.0464 (18)	0.056 (2)	−0.0136 (17)	−0.0088 (16)	0.0034 (16)
C4	0.0454 (19)	0.065 (2)	0.074 (3)	−0.0139 (18)	−0.0001 (17)	0.0101 (19)
C5	0.0441 (18)	0.058 (2)	0.063 (2)	0.0016 (16)	0.0069 (15)	0.0098 (17)
C6	0.0413 (16)	0.0405 (15)	0.0340 (16)	0.0009 (13)	0.0004 (12)	0.0080 (12)
C7	0.0454 (16)	0.0353 (15)	0.0355 (16)	0.0031 (13)	0.0034 (12)	0.0027 (12)
C8	0.0464 (17)	0.0298 (14)	0.0357 (16)	−0.0021 (12)	0.0047 (12)	−0.0002 (11)
C9	0.0470 (17)	0.0435 (17)	0.0393 (17)	0.0018 (13)	0.0115 (13)	−0.0037 (13)
C10	0.083 (2)	0.0438 (19)	0.047 (2)	−0.0007 (17)	0.0053 (18)	−0.0021 (15)
C11	0.118 (4)	0.063 (2)	0.056 (3)	0.003 (2)	0.004 (2)	0.010 (2)
C12	0.097 (3)	0.107 (4)	0.037 (2)	−0.008 (3)	−0.004 (2)	−0.001 (2)
C13	0.099 (3)	0.098 (3)	0.042 (2)	−0.033 (3)	0.008 (2)	−0.012 (2)
C14	0.078 (2)	0.061 (2)	0.047 (2)	−0.0192 (19)	0.0146 (18)	−0.0042 (17)
C15	0.057 (2)	0.051 (2)	0.047 (2)	0.0062 (16)	0.0141 (16)	0.0018 (14)
C16	0.080 (3)	0.051 (2)	0.070 (3)	−0.0090 (18)	0.029 (2)	−0.0180 (17)
Br1	0.0956 (5)	0.0997 (5)	0.0870 (5)	−0.0029 (3)	−0.0142 (3)	−0.0100 (3)
C17	0.067 (4)	0.023 (2)	0.071 (4)	0.016 (2)	0.008 (3)	0.009 (2)
Br1A	0.118 (6)	0.078 (3)	0.192 (7)	0.027 (3)	0.004 (4)	−0.038 (4)
C17A	0.067 (4)	0.023 (2)	0.071 (4)	0.016 (2)	0.008 (3)	0.009 (2)
N1	0.0432 (14)	0.0363 (13)	0.0356 (14)	−0.0015 (10)	0.0062 (10)	−0.0010 (10)
O1	0.0659 (15)	0.0400 (12)	0.0727 (17)	0.0185 (10)	0.0151 (12)	0.0072 (10)
O2	0.0369 (11)	0.0555 (13)	0.0640 (15)	−0.0048 (10)	0.0040 (10)	−0.0037 (11)
O3	0.0651 (17)	0.0646 (16)	0.111 (2)	0.0071 (13)	0.0367 (16)	−0.0143 (15)
S1	0.0431 (4)	0.0378 (4)	0.0458 (5)	0.0067 (3)	0.0078 (3)	0.0012 (3)

C1—C2	1.387 (4)	C12—C13	1.366 (6)
C1—C6	1.398 (4)	C12—H12	0.9300
C1—N1	1.420 (4)	C13—C14	1.359 (5)
C2—C3	1.388 (5)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.379 (5)	C15—O3	1.216 (4)
C3—H3	0.9300	C15—C16	1.511 (4)
C4—C5	1.389 (5)	C16—C17	1.5190 (10)
C4—H4	0.9300	C16—C17A	1.520 (5)
C5—C6	1.382 (4)	C16—Br1A	1.849 (4)
C5—H5	0.9300	C16—Br1	1.9092 (10)
C6—C7	1.450 (4)	C16—H16A	0.9800
C7—C8	1.352 (4)	C16—H16B	0.9800
C7—C15	1.460 (4)	C17—H17A	0.9600
C8—N1	1.386 (3)	C17—H17B	0.9600
C8—H8	0.9300	C17—H17C	0.9600
C9—C10	1.388 (4)	C17A—H17D	0.9600
C9—C14	1.392 (5)	C17A—H17E	0.9600
C9—S1	1.743 (3)	C17A—H17F	0.9600
C10—C11	1.368 (5)	N1—S1	1.669 (2)
C10—H10	0.9300	O1—S1	1.422 (2)
C11—C12	1.384 (6)	O2—S1	1.417 (2)
C11—H11	0.9300

C2—C1—C6	123.3 (3)	C13—C14—C9	119.1 (3)
C2—C1—N1	129.7 (3)	C13—C14—H14	120.5
C6—C1—N1	107.0 (2)	C9—C14—H14	120.5
C1—C2—C3	115.9 (3)	O3—C15—C7	121.0 (3)
C1—C2—H2	122.0	O3—C15—C16	121.8 (3)
C3—C2—H2	122.0	C7—C15—C16	117.1 (3)
C4—C3—C2	121.9 (3)	C15—C16—C17	117.9 (4)
C4—C3—H3	119.0	C15—C16—C17A	117.7 (10)
C2—C3—H3	119.0	C15—C16—Br1A	111.9 (4)
C3—C4—C5	121.3 (3)	C17A—C16—Br1A	113.8 (6)
C3—C4—H4	119.4	C15—C16—Br1	107.61 (19)
C5—C4—H4	119.4	C17—C16—Br1	109.7 (4)
C6—C5—C4	118.4 (3)	C15—C16—H16A	107.0
C6—C5—H5	120.8	C17—C16—H16A	107.0
C4—C5—H5	120.8	Br1—C16—H16A	107.0
C5—C6—C1	119.2 (3)	C15—C16—H16B	103.8
C5—C6—C7	133.2 (3)	C17A—C16—H16B	103.8
C1—C6—C7	107.6 (2)	Br1A—C16—H16B	103.8
C8—C7—C6	107.0 (2)	C16—C17—H17A	109.5
C8—C7—C15	126.5 (3)	C16—C17—H17B	109.5
C6—C7—C15	126.5 (3)	H17A—C17—H17B	109.5
C7—C8—N1	110.6 (2)	C16—C17—H17C	109.5
C7—C8—H8	124.7	H17A—C17—H17C	109.5
N1—C8—H8	124.7	H17B—C17—H17C	109.5
C10—C9—C14	121.0 (3)	C16—C17A—H17D	109.5
C10—C9—S1	118.7 (2)	C16—C17A—H17E	109.5
C14—C9—S1	120.3 (2)	H17D—C17A—H17E	109.5
C11—C10—C9	118.8 (3)	C16—C17A—H17F	109.5
C11—C10—H10	120.6	H17D—C17A—H17F	109.5
C9—C10—H10	120.6	H17E—C17A—H17F	109.5
C10—C11—C12	120.0 (4)	C8—N1—C1	107.9 (2)
C10—C11—H11	120.0	C8—N1—S1	122.02 (19)
C12—C11—H11	120.0	C1—N1—S1	127.03 (19)
C13—C12—C11	120.7 (4)	O2—S1—O1	120.71 (14)
C13—C12—H12	119.6	O2—S1—N1	105.46 (12)
C11—C12—H12	119.6	O1—S1—N1	105.86 (13)
C14—C13—C12	120.4 (4)	O2—S1—C9	110.36 (14)
C14—C13—H13	119.8	O1—S1—C9	108.50 (14)
C12—C13—H13	119.8	N1—S1—C9	104.67 (13)

C6—C1—C2—C3	0.7 (4)	C6—C7—C15—C16	177.8 (2)
N1—C1—C2—C3	178.7 (3)	O3—C15—C16—C17	−37.3 (5)
C1—C2—C3—C4	0.5 (5)	C7—C15—C16—C17	140.8 (4)
C2—C3—C4—C5	−1.1 (5)	O3—C15—C16—C17A	106.8 (12)
C3—C4—C5—C6	0.4 (5)	C7—C15—C16—C17A	−75.1 (12)
C4—C5—C6—C1	0.8 (4)	O3—C15—C16—Br1A	−27.8 (5)
C4—C5—C6—C7	−179.8 (3)	C7—C15—C16—Br1A	150.3 (4)
C2—C1—C6—C5	−1.4 (4)	O3—C15—C16—Br1	87.4 (3)
N1—C1—C6—C5	−179.7 (2)	C7—C15—C16—Br1	−94.5 (3)
C2—C1—C6—C7	179.1 (3)	C7—C8—N1—C1	1.7 (3)
N1—C1—C6—C7	0.7 (3)	C7—C8—N1—S1	163.2 (2)
C5—C6—C7—C8	−179.2 (3)	C2—C1—N1—C8	−179.7 (3)
C1—C6—C7—C8	0.3 (3)	C6—C1—N1—C8	−1.5 (3)
C5—C6—C7—C15	0.7 (5)	C2—C1—N1—S1	20.1 (4)
C1—C6—C7—C15	−179.8 (3)	C6—C1—N1—S1	−161.7 (2)
C6—C7—C8—N1	−1.3 (3)	C8—N1—S1—O2	28.1 (2)
C15—C7—C8—N1	178.9 (3)	C1—N1—S1—O2	−174.2 (2)
C14—C9—C10—C11	0.7 (5)	C8—N1—S1—O1	157.1 (2)
S1—C9—C10—C11	−179.1 (3)	C1—N1—S1—O1	−45.2 (3)
C9—C10—C11—C12	0.0 (6)	C8—N1—S1—C9	−88.4 (2)
C10—C11—C12—C13	−0.8 (7)	C1—N1—S1—C9	69.3 (2)
C11—C12—C13—C14	1.1 (7)	C10—C9—S1—O2	−21.3 (3)
C12—C13—C14—C9	−0.4 (6)	C14—C9—S1—O2	158.9 (3)
C10—C9—C14—C13	−0.4 (5)	C10—C9—S1—O1	−155.7 (3)
S1—C9—C14—C13	179.3 (3)	C14—C9—S1—O1	24.6 (3)
C8—C7—C15—O3	175.7 (3)	C10—C9—S1—N1	91.7 (3)
C6—C7—C15—O3	−4.1 (5)	C14—C9—S1—N1	−88.0 (3)
C8—C7—C15—C16	−2.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.57	3.312 (4)	137
C10—H10···O1ⁱ	0.93	2.44	3.280 (4)	150
C12—H12···Cg2ⁱⁱ	0.93	2.72	3.528 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.93	2.57	3.312 (4)	137
C10—H10⋯O1ⁱ	0.93	2.44	3.280 (4)	150
C12—H12⋯Cg2ⁱⁱ	0.93	2.72	3.528 (2)	146

Symmetry codes: (i) ; (ii) .

7 in total

1. Antifungal activity of venenatine, an indole alkaloid isolated from Alstonia venenata.

Authors: U P Singh; B K Sarma; P K Mishra; A B Ray
Journal: Folia Microbiol (Praha) Date: 2000 Impact factor: 2.099

2. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

3. Synthesis and antitumor activity of substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones.

Authors: A Andreani; M Granaiola; A Leoni; A Locatelli; R Morigi; M Rambaldi; G Giorgi; L Salvini; V Garaliene
Journal: Anticancer Drug Des Date: 2001 Apr-Jun

4. Synthesis of 1-(6-chloro-1,1-dioxo-1,4,2-benzodithiazin-3-yl)semi-carbazides and their transformation into 4-chloro-2-mercapto-N-(4,5-dihydro-5-oxo-4-phenyl-1H-1,2,4-triazol-3-yl)benzenesulfonamides as potential anticancer and anti-HIV agents.

Authors: Elzbieta Pomarnacka; Iwona Kozlarska-Kedra
Journal: Farmaco Date: 2003-06