Literature DB >> 21589125

(4-Bromo-phen-yl)(1-phenyl-sulfonyl-1H-indol-2-yl)methanone.

G Chakkaravarthi, R Panchatcharam, V Dhayalan, A K Mohanakrishnan, V Manivannan.

Abstract

In the title compound, C(21)H(14)BrNO(3)S, the indole ring system forms dihedral angles of 65.64 (8) and 59.30 (8)°, respectively, with the phenyl and bromo-phenyl rings. In the crystal, mol-ecules are connected by a C-H⋯O hydrogen bond, forming a chain along [101]. The chains are further connected by weak inter-molecular C-H⋯π inter-actions, forming a layer parallel to the ac plane.

Entities: Chemical Disease Gene

Year: 2010 PMID： 21589125 PMCID： PMC3009294 DOI： 10.1107/S160053681004198X

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

Related literature

For the biological activity of indole derivatives, see: Joshi & Chand (1982 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶); Poter et al. (1977 ▶). For related structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶). 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

C21H14BrNO3S M = 440.30 Monoclinic, a = 8.482 (3) Å b = 25.780 (4) Å c = 8.690 (3) Å β = 93.388 (3)° V = 1896.9 (10) Å3 Z = 4 Mo Kα radiation μ = 2.30 mm−1 T = 295 K 0.24 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.609, T max = 0.656 18123 measured reflections 4736 independent reflections 2944 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.111 S = 1.03 4736 reflections 244 parameters H-atom parameters constrained Δρmax = 0.62 e Å−3 Δρmin = −0.46 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 datablocks I, global. DOI: 10.1107/S160053681004198X/is2617sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053681004198X/is2617Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₁H₁₄BrNO₃S	F(000) = 888
M_r = 440.30	D_x = 1.542 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4249 reflections
a = 8.482 (3) Å	θ = 2.5–24.4°
b = 25.780 (4) Å	µ = 2.30 mm⁻¹
c = 8.690 (3) Å	T = 295 K
β = 93.388 (3)°	Block, colourless
V = 1896.9 (10) Å³	0.24 × 0.22 × 0.20 mm
Z = 4

Bruker Kappa APEXII diffractometer	4736 independent reflections
Radiation source: fine-focus sealed tube	2944 reflections with I > 2σ(I)
graphite	R_int = 0.035
ω and φ scans	θ_max = 28.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
T_min = 0.609, T_max = 0.656	k = −29→34
18123 measured reflections	l = −9→11

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0445P)² + 0.6759P] where P = (F_o² + 2F_c²)/3
4736 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

	x	y	z	U_iso*/U_eq
Br1	0.24312 (5)	0.018422 (12)	0.53534 (5)	0.09126 (18)
S1	0.26404 (8)	0.34303 (3)	0.83609 (7)	0.04855 (18)
O1	0.3198 (2)	0.38893 (8)	0.9118 (2)	0.0648 (5)
O2	0.2576 (3)	0.29550 (8)	0.9169 (2)	0.0737 (6)
O3	0.5440 (2)	0.24395 (7)	0.8349 (2)	0.0671 (6)
N1	0.3837 (2)	0.33357 (7)	0.6910 (2)	0.0421 (5)
C1	0.0793 (3)	0.35548 (11)	0.7418 (3)	0.0494 (6)
C2	0.0204 (4)	0.40492 (12)	0.7428 (4)	0.0703 (9)
H2	0.0751	0.4312	0.7965	0.084*
C3	−0.1230 (4)	0.41519 (17)	0.6619 (5)	0.0963 (12)
H3	−0.1637	0.4487	0.6586	0.116*
C4	−0.2035 (4)	0.3756 (2)	0.5872 (5)	0.1035 (14)
H4	−0.3000	0.3824	0.5347	0.124*
C5	−0.1456 (4)	0.32696 (18)	0.5883 (4)	0.0901 (12)
H5	−0.2021	0.3006	0.5369	0.108*
C6	−0.0021 (4)	0.31602 (12)	0.6658 (3)	0.0650 (8)
H6	0.0386	0.2825	0.6665	0.078*
C7	0.4047 (3)	0.28357 (9)	0.6256 (3)	0.0410 (5)
C8	0.4166 (3)	0.28833 (10)	0.4728 (3)	0.0488 (6)
H8	0.4315	0.2612	0.4045	0.059*
C9	0.4027 (3)	0.34192 (10)	0.4327 (3)	0.0477 (6)
C10	0.4108 (4)	0.36829 (14)	0.2933 (4)	0.0706 (9)
H10	0.4263	0.3505	0.2024	0.085*
C11	0.3955 (4)	0.42089 (15)	0.2939 (4)	0.0827 (11)
H11	0.4003	0.4391	0.2019	0.099*
C12	0.3731 (4)	0.44741 (12)	0.4272 (5)	0.0769 (10)
H12	0.3629	0.4833	0.4230	0.092*
C13	0.3650 (3)	0.42278 (11)	0.5686 (4)	0.0613 (7)
H13	0.3494	0.4410	0.6587	0.074*
C14	0.3816 (3)	0.36928 (9)	0.5669 (3)	0.0438 (6)
C15	0.4561 (3)	0.23788 (10)	0.7209 (3)	0.0471 (6)
C16	0.4037 (3)	0.18560 (9)	0.6675 (3)	0.0430 (6)
C17	0.2741 (3)	0.17786 (10)	0.5660 (3)	0.0486 (6)
H17	0.2187	0.2062	0.5244	0.058*
C18	0.2266 (3)	0.12794 (11)	0.5260 (3)	0.0566 (7)
H18	0.1389	0.1226	0.4584	0.068*
C19	0.3100 (3)	0.08671 (10)	0.5870 (3)	0.0566 (7)
C20	0.4411 (4)	0.09344 (11)	0.6858 (4)	0.0656 (8)
H20	0.4980	0.0650	0.7246	0.079*
C21	0.4865 (3)	0.14285 (10)	0.7260 (3)	0.0586 (7)
H21	0.5744	0.1478	0.7936	0.070*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1039 (3)	0.04279 (18)	0.1244 (4)	−0.01215 (17)	−0.0165 (2)	−0.00695 (18)
S1	0.0576 (4)	0.0482 (4)	0.0396 (3)	0.0031 (3)	0.0004 (3)	−0.0035 (3)
O1	0.0676 (13)	0.0651 (12)	0.0596 (11)	0.0067 (10)	−0.0144 (10)	−0.0246 (10)
O2	0.0985 (17)	0.0670 (13)	0.0573 (12)	0.0100 (11)	0.0197 (11)	0.0186 (10)
O3	0.0788 (14)	0.0531 (11)	0.0650 (12)	0.0036 (10)	−0.0339 (11)	−0.0042 (9)
N1	0.0464 (12)	0.0357 (10)	0.0439 (11)	0.0020 (9)	−0.0010 (9)	0.0010 (8)
C1	0.0446 (15)	0.0566 (15)	0.0475 (14)	−0.0042 (12)	0.0073 (12)	−0.0093 (12)
C2	0.0522 (18)	0.066 (2)	0.092 (2)	0.0062 (15)	−0.0045 (16)	−0.0181 (17)
C3	0.059 (2)	0.103 (3)	0.125 (3)	0.022 (2)	−0.008 (2)	−0.009 (3)
C4	0.045 (2)	0.163 (5)	0.102 (3)	−0.002 (3)	−0.0044 (19)	−0.031 (3)
C5	0.054 (2)	0.129 (4)	0.088 (3)	−0.031 (2)	0.0063 (18)	−0.041 (2)
C6	0.0609 (19)	0.0685 (19)	0.0671 (19)	−0.0180 (15)	0.0171 (16)	−0.0198 (15)
C7	0.0391 (13)	0.0378 (12)	0.0452 (14)	0.0000 (10)	−0.0038 (10)	−0.0029 (10)
C8	0.0482 (15)	0.0539 (15)	0.0439 (15)	−0.0019 (12)	−0.0018 (12)	−0.0090 (12)
C9	0.0382 (14)	0.0604 (16)	0.0438 (14)	−0.0065 (12)	−0.0029 (11)	0.0067 (12)
C10	0.071 (2)	0.086 (2)	0.0539 (18)	−0.0102 (17)	−0.0008 (15)	0.0200 (16)
C11	0.079 (2)	0.095 (3)	0.073 (2)	−0.014 (2)	−0.0080 (18)	0.041 (2)
C12	0.067 (2)	0.0518 (17)	0.110 (3)	−0.0056 (15)	−0.0073 (19)	0.0329 (19)
C13	0.0565 (18)	0.0475 (15)	0.079 (2)	−0.0009 (13)	−0.0005 (15)	0.0073 (14)
C14	0.0349 (13)	0.0428 (13)	0.0533 (15)	−0.0032 (10)	−0.0025 (11)	0.0084 (11)
C15	0.0449 (14)	0.0445 (13)	0.0508 (15)	0.0057 (11)	−0.0058 (12)	−0.0023 (11)
C16	0.0421 (14)	0.0387 (12)	0.0475 (14)	0.0047 (10)	−0.0035 (11)	0.0000 (10)
C17	0.0422 (14)	0.0431 (13)	0.0590 (16)	0.0047 (11)	−0.0100 (12)	−0.0004 (11)
C18	0.0470 (16)	0.0503 (16)	0.0707 (18)	−0.0045 (12)	−0.0114 (14)	−0.0017 (13)
C19	0.0585 (17)	0.0387 (13)	0.0719 (19)	−0.0029 (12)	−0.0005 (14)	−0.0020 (12)
C20	0.071 (2)	0.0425 (15)	0.080 (2)	0.0129 (14)	−0.0178 (16)	0.0013 (14)
C21	0.0556 (17)	0.0489 (15)	0.0685 (18)	0.0082 (13)	−0.0212 (14)	0.0000 (13)

Br1—C19	1.895 (3)	C8—H8	0.9300
S1—O2	1.415 (2)	C9—C14	1.384 (4)
S1—O1	1.4211 (19)	C9—C10	1.394 (4)
S1—N1	1.682 (2)	C10—C11	1.362 (5)
S1—C1	1.754 (3)	C10—H10	0.9300
O3—C15	1.215 (3)	C11—C12	1.368 (5)
N1—C14	1.417 (3)	C11—H11	0.9300
N1—C7	1.424 (3)	C12—C13	1.388 (4)
C1—C2	1.369 (4)	C12—H12	0.9300
C1—C6	1.376 (4)	C13—C14	1.386 (3)
C2—C3	1.394 (5)	C13—H13	0.9300
C2—H2	0.9300	C15—C16	1.485 (3)
C3—C4	1.370 (5)	C16—C17	1.382 (3)
C3—H3	0.9300	C16—C21	1.387 (3)
C4—C5	1.346 (6)	C17—C18	1.387 (4)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.385 (5)	C18—C19	1.367 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.375 (4)
C7—C8	1.343 (3)	C20—C21	1.370 (4)
C7—C15	1.490 (3)	C20—H20	0.9300
C8—C9	1.428 (4)	C21—H21	0.9300

O2—S1—O1	120.86 (13)	C11—C10—C9	118.2 (3)
O2—S1—N1	106.80 (11)	C11—C10—H10	120.9
O1—S1—N1	105.58 (12)	C9—C10—H10	120.9
O2—S1—C1	109.31 (14)	C10—C11—C12	121.2 (3)
O1—S1—C1	109.10 (12)	C10—C11—H11	119.4
N1—S1—C1	103.79 (11)	C12—C11—H11	119.4
C14—N1—C7	106.31 (19)	C11—C12—C13	122.5 (3)
C14—N1—S1	119.67 (16)	C11—C12—H12	118.7
C7—N1—S1	121.71 (16)	C13—C12—H12	118.7
C2—C1—C6	121.2 (3)	C14—C13—C12	115.8 (3)
C2—C1—S1	118.9 (2)	C14—C13—H13	122.1
C6—C1—S1	119.9 (2)	C12—C13—H13	122.1
C1—C2—C3	118.8 (3)	C9—C14—C13	122.3 (2)
C1—C2—H2	120.6	C9—C14—N1	108.3 (2)
C3—C2—H2	120.6	C13—C14—N1	129.4 (2)
C4—C3—C2	119.6 (4)	O3—C15—C16	122.0 (2)
C4—C3—H3	120.2	O3—C15—C7	119.8 (2)
C2—C3—H3	120.2	C16—C15—C7	118.1 (2)
C5—C4—C3	121.3 (4)	C17—C16—C21	119.0 (2)
C5—C4—H4	119.4	C17—C16—C15	122.8 (2)
C3—C4—H4	119.4	C21—C16—C15	118.1 (2)
C4—C5—C6	120.2 (3)	C16—C17—C18	120.2 (2)
C4—C5—H5	119.9	C16—C17—H17	119.9
C6—C5—H5	119.9	C18—C17—H17	119.9
C1—C6—C5	119.0 (3)	C19—C18—C17	119.2 (2)
C1—C6—H6	120.5	C19—C18—H18	120.4
C5—C6—H6	120.5	C17—C18—H18	120.4
C8—C7—N1	109.3 (2)	C18—C19—C20	121.7 (3)
C8—C7—C15	125.8 (2)	C18—C19—Br1	119.3 (2)
N1—C7—C15	122.2 (2)	C20—C19—Br1	119.0 (2)
C7—C8—C9	108.6 (2)	C21—C20—C19	118.8 (3)
C7—C8—H8	125.7	C21—C20—H20	120.6
C9—C8—H8	125.7	C19—C20—H20	120.6
C14—C9—C10	120.0 (3)	C20—C21—C16	121.1 (2)
C14—C9—C8	107.5 (2)	C20—C21—H21	119.4
C10—C9—C8	132.5 (3)	C16—C21—H21	119.4

O2—S1—N1—C14	163.63 (18)	C10—C11—C12—C13	0.1 (5)
O1—S1—N1—C14	−66.5 (2)	C11—C12—C13—C14	0.2 (5)
C1—S1—N1—C14	48.2 (2)	C10—C9—C14—C13	1.2 (4)
O2—S1—N1—C7	26.6 (2)	C8—C9—C14—C13	179.6 (2)
O1—S1—N1—C7	156.43 (18)	C10—C9—C14—N1	−177.8 (2)
C1—S1—N1—C7	−88.8 (2)	C8—C9—C14—N1	0.6 (3)
O2—S1—C1—C2	138.5 (2)	C12—C13—C14—C9	−0.9 (4)
O1—S1—C1—C2	4.3 (3)	C12—C13—C14—N1	177.9 (3)
N1—S1—C1—C2	−107.9 (2)	C7—N1—C14—C9	−0.8 (3)
O2—S1—C1—C6	−42.9 (3)	S1—N1—C14—C9	−143.64 (18)
O1—S1—C1—C6	−177.1 (2)	C7—N1—C14—C13	−179.7 (2)
N1—S1—C1—C6	70.7 (2)	S1—N1—C14—C13	37.5 (3)
C6—C1—C2—C3	−1.5 (5)	C8—C7—C15—O3	127.2 (3)
S1—C1—C2—C3	177.1 (3)	N1—C7—C15—O3	−32.1 (4)
C1—C2—C3—C4	1.8 (6)	C8—C7—C15—C16	−49.7 (4)
C2—C3—C4—C5	−1.1 (7)	N1—C7—C15—C16	151.0 (2)
C3—C4—C5—C6	0.0 (6)	O3—C15—C16—C17	162.2 (3)
C2—C1—C6—C5	0.5 (4)	C7—C15—C16—C17	−20.9 (4)
S1—C1—C6—C5	−178.1 (2)	O3—C15—C16—C21	−16.0 (4)
C4—C5—C6—C1	0.3 (5)	C7—C15—C16—C21	160.8 (2)
C14—N1—C7—C8	0.7 (3)	C21—C16—C17—C18	1.2 (4)
S1—N1—C7—C8	142.63 (19)	C15—C16—C17—C18	−177.0 (2)
C14—N1—C7—C15	163.0 (2)	C16—C17—C18—C19	−0.5 (4)
S1—N1—C7—C15	−55.1 (3)	C17—C18—C19—C20	−0.8 (5)
N1—C7—C8—C9	−0.4 (3)	C17—C18—C19—Br1	178.9 (2)
C15—C7—C8—C9	−161.9 (2)	C18—C19—C20—C21	1.4 (5)
C7—C8—C9—C14	−0.1 (3)	Br1—C19—C20—C21	−178.3 (2)
C7—C8—C9—C10	178.0 (3)	C19—C20—C21—C16	−0.7 (5)
C14—C9—C10—C11	−0.8 (4)	C17—C16—C21—C20	−0.6 (4)
C8—C9—C10—C11	−178.7 (3)	C15—C16—C21—C20	177.7 (3)
C9—C10—C11—C12	0.2 (5)

Cg1 and Cg2 are the centroids of the N1/C7/C8/C9/C14 and C9—C14 rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O3ⁱ	0.93	2.50	3.383 (3)	158
C4—H4···Cg1ⁱⁱ	0.93	2.67	3.635 (4)	127
C4—H4···Cg2ⁱⁱ	0.93	2.76	3.681 (4)	169

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C7/C8/C9/C14 and C9–C14 rings, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O3ⁱ	0.93	2.50	3.383 (3)	158
C4—H4⋯Cg1ⁱⁱ	0.93	2.67	3.635 (4)	127
C4—H4⋯Cg2ⁱⁱ	0.93	2.76	3.681 (4)	169

Symmetry codes: (i) ; (ii) .

6 in total

1. Indole alkaloids from Balansia epichloë (Weese).

Authors: J K Porter; C W Bacon; J D Robbins; D S Himmelsbach; H C Higman
Journal: J Agric Food Chem Date: 1976 Jan-Feb Impact factor: 5.279

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Authors: George M Sheldrick
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Journal: Pharmazie Date: 1982-01 Impact factor: 1.267

4. (2-Methyl-1-phenyl-sulfonyl-1H-indol-3-yl)methanol.

Authors: G Chakkaravarthi; V Dhayalan; A K Mohanakrishnan; V Manivannan
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-01-30

5. 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

6. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20

6 in total

5 in total