Literature DB >> 24454236

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

M Umadevi1, V Saravanan2, R Yamuna3, A K Mohanakrishnan2, G Chakkaravarthi4.   

Abstract

In the title compound, C18H16BrNO3S, the dihedral angle between the phenyl ring and the indole ring system is 89.91 (11)°. The mol-ecular structure features weak C-H⋯O and C-H⋯Br hydrogen bonds. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming chains along the a-axis direction. The chains are further linked by C-H⋯π inter-actions, forming a layer parallel to the ab plane.

Entities:  

Year:  2013        PMID： 24454236      PMCID： PMC3885060          DOI： 10.1107/S1600536813031413

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


Related literature

For the biological activity of indole derivatives, see: Chai et al. (2006 ▶); Nieto et al. (2005 ▶). 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

C18H16BrNO3S M = 406.29 Monoclinic, a = 10.2772 (7) Å b = 8.6610 (6) Å c = 18.8980 (14) Å β = 90.676 (2)° V = 1682.0 (2) Å3 Z = 4 Mo Kα radiation μ = 2.58 mm−1 T = 295 K 0.38 × 0.34 × 0.30 mm

Data collection

Bruker Kappa APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.397, T max = 0.461 25944 measured reflections 7303 independent reflections 3726 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.133 S = 1.00 7303 reflections 218 parameters H-atom parameters constrained Δρmax = 1.11 e Å−3 Δρmin = −0.90 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/S1600536813031413/is5323sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031413/is5323Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813031413/is5323Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H16BrNO3SF(000) = 824
Mr = 406.29Dx = 1.604 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5675 reflections
a = 10.2772 (7) Åθ = 2.6–28.2°
b = 8.6610 (6) ŵ = 2.58 mm−1
c = 18.8980 (14) ÅT = 295 K
β = 90.676 (2)°Block, colourless
V = 1682.0 (2) Å30.38 × 0.34 × 0.30 mm
Z = 4
Bruker Kappa APEXII diffractometer7303 independent reflections
Radiation source: fine-focus sealed tube3726 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω and φ scanθmax = 35.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −16→15
Tmin = 0.397, Tmax = 0.461k = −13→13
25944 measured reflectionsl = −30→30
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0528P)2 + 0.8633P] where P = (Fo2 + 2Fc2)/3
7303 reflections(Δ/σ)max < 0.001
218 parametersΔρmax = 1.11 e Å−3
0 restraintsΔρmin = −0.90 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.
xyzUiso*/Ueq
C10.3590 (2)0.2855 (3)1.15387 (11)0.0316 (4)
C20.4906 (2)0.2669 (3)1.14030 (14)0.0388 (5)
H20.53490.33871.11300.047*
C30.5545 (2)0.1404 (3)1.16792 (14)0.0478 (6)
H30.64290.12761.15990.057*
C40.4891 (3)0.0341 (4)1.20682 (14)0.0527 (7)
H40.5334−0.05081.22510.063*
C50.3573 (3)0.0506 (4)1.21952 (16)0.0594 (8)
H50.3134−0.02361.24560.071*
C60.2917 (2)0.1775 (3)1.19338 (14)0.0468 (6)
H60.20350.19061.20210.056*
C70.03158 (18)0.3688 (2)1.08099 (11)0.0276 (4)
C8−0.0180 (2)0.2867 (2)1.02518 (11)0.0290 (4)
C90.0851 (2)0.2600 (2)0.97521 (11)0.0304 (4)
C100.0935 (2)0.1861 (3)0.90938 (12)0.0407 (5)
H100.02170.13590.88980.049*
C110.2110 (3)0.1894 (3)0.87400 (14)0.0492 (7)
H110.21730.14070.83030.059*
C120.3188 (3)0.2635 (3)0.90221 (14)0.0491 (7)
H120.39570.26460.87680.059*
C130.3152 (2)0.3356 (3)0.96705 (13)0.0411 (6)
H130.38800.38470.98610.049*
C140.19702 (19)0.3317 (3)1.00296 (11)0.0306 (4)
C15−0.0399 (2)0.4324 (3)1.14247 (12)0.0358 (5)
H15A−0.12350.47171.12640.043*
H15B0.00900.51791.16250.043*
C16−0.1576 (2)0.2394 (3)1.02006 (13)0.0355 (5)
C17−0.2006 (2)0.1315 (3)0.96217 (14)0.0419 (6)
H17A−0.14400.04180.96210.050*
H17B−0.19220.18290.91690.050*
C18−0.3408 (3)0.0787 (4)0.97091 (16)0.0561 (7)
H18A−0.34940.02681.01550.084*
H18B−0.36390.00930.93320.084*
H18C−0.39750.16680.96960.084*
N10.16494 (16)0.3982 (2)1.06867 (9)0.0299 (4)
O10.21453 (16)0.5195 (2)1.18571 (10)0.0523 (5)
O20.36972 (17)0.5470 (2)1.08811 (11)0.0523 (5)
O3−0.23528 (17)0.2863 (3)1.06323 (11)0.0571 (5)
S10.28085 (5)0.45547 (7)1.12687 (3)0.03548 (14)
Br1−0.06733 (3)0.27582 (4)1.215850 (15)0.06069 (12)
U11U22U33U12U13U23
C10.0272 (9)0.0409 (12)0.0268 (10)0.0035 (9)−0.0028 (8)−0.0044 (9)
C20.0273 (10)0.0475 (14)0.0417 (13)−0.0015 (9)0.0007 (9)−0.0020 (11)
C30.0305 (11)0.0644 (18)0.0484 (15)0.0119 (11)−0.0046 (10)−0.0013 (13)
C40.0490 (14)0.0675 (19)0.0415 (14)0.0214 (14)−0.0025 (12)0.0139 (13)
C50.0545 (16)0.072 (2)0.0515 (16)0.0105 (15)0.0129 (13)0.0290 (15)
C60.0332 (11)0.0619 (17)0.0456 (15)0.0068 (11)0.0090 (10)0.0126 (13)
C70.0253 (8)0.0293 (11)0.0281 (10)0.0034 (8)0.0001 (8)0.0040 (8)
C80.0285 (9)0.0303 (11)0.0281 (10)0.0006 (8)−0.0007 (8)0.0036 (8)
C90.0324 (10)0.0318 (11)0.0270 (10)0.0045 (8)0.0001 (8)0.0047 (8)
C100.0456 (13)0.0457 (14)0.0307 (12)0.0055 (11)−0.0012 (10)−0.0033 (10)
C110.0534 (15)0.0605 (17)0.0339 (13)0.0191 (13)0.0064 (11)−0.0038 (12)
C120.0409 (12)0.0657 (18)0.0411 (14)0.0144 (12)0.0138 (11)0.0046 (13)
C130.0302 (10)0.0525 (15)0.0409 (13)0.0053 (10)0.0052 (10)0.0047 (11)
C140.0283 (9)0.0341 (11)0.0294 (10)0.0056 (8)0.0008 (8)0.0040 (9)
C150.0331 (10)0.0424 (13)0.0321 (11)0.0050 (9)0.0036 (9)−0.0016 (10)
C160.0308 (10)0.0373 (13)0.0383 (12)−0.0023 (9)−0.0034 (9)0.0044 (10)
C170.0404 (12)0.0399 (14)0.0452 (14)−0.0030 (10)−0.0091 (11)0.0015 (11)
C180.0482 (15)0.0594 (18)0.0606 (18)−0.0179 (13)−0.0115 (13)−0.0020 (15)
N10.0244 (7)0.0356 (10)0.0296 (9)0.0016 (7)−0.0013 (7)−0.0002 (8)
O10.0429 (9)0.0590 (12)0.0548 (11)0.0097 (8)−0.0095 (8)−0.0286 (9)
O20.0412 (9)0.0383 (10)0.0774 (14)−0.0094 (8)−0.0049 (9)0.0062 (10)
O30.0341 (9)0.0783 (14)0.0593 (13)−0.0117 (9)0.0086 (8)−0.0156 (11)
S10.0297 (2)0.0333 (3)0.0434 (3)0.0002 (2)−0.0058 (2)−0.0068 (2)
Br10.04826 (16)0.0928 (3)0.04125 (16)0.01267 (15)0.01231 (12)0.02479 (15)
C1—C61.386 (3)C11—C121.382 (4)
C1—C21.389 (3)C11—H110.9300
C1—S11.750 (2)C12—C131.376 (4)
C2—C31.376 (4)C12—H120.9300
C2—H20.9300C13—C141.399 (3)
C3—C41.361 (4)C13—H130.9300
C3—H30.9300C14—N11.411 (3)
C4—C51.385 (4)C15—Br11.963 (2)
C4—H40.9300C15—H15A0.9700
C5—C61.378 (4)C15—H15B0.9700
C5—H50.9300C16—O31.218 (3)
C6—H60.9300C16—C171.502 (3)
C7—C81.366 (3)C17—C181.522 (3)
C7—N11.416 (2)C17—H17A0.9700
C7—C151.488 (3)C17—H17B0.9700
C8—C91.446 (3)C18—H18A0.9600
C8—C161.494 (3)C18—H18B0.9600
C9—C101.403 (3)C18—H18C0.9600
C9—C141.403 (3)N1—S11.6864 (18)
C10—C111.387 (4)O1—S11.4236 (18)
C10—H100.9300O2—S11.4193 (19)
C6—C1—C2121.0 (2)C12—C13—C14117.0 (2)
C6—C1—S1119.62 (17)C12—C13—H13121.5
C2—C1—S1119.21 (19)C14—C13—H13121.5
C3—C2—C1118.9 (2)C13—C14—C9122.8 (2)
C3—C2—H2120.6C13—C14—N1129.1 (2)
C1—C2—H2120.6C9—C14—N1108.08 (17)
C4—C3—C2120.5 (2)C7—C15—Br1111.86 (16)
C4—C3—H3119.8C7—C15—H15A109.2
C2—C3—H3119.8Br1—C15—H15A109.2
C3—C4—C5120.9 (2)C7—C15—H15B109.2
C3—C4—H4119.5Br1—C15—H15B109.2
C5—C4—H4119.5H15A—C15—H15B107.9
C6—C5—C4119.7 (3)O3—C16—C8120.1 (2)
C6—C5—H5120.2O3—C16—C17120.4 (2)
C4—C5—H5120.2C8—C16—C17119.5 (2)
C5—C6—C1119.1 (2)C16—C17—C18112.2 (2)
C5—C6—H6120.5C16—C17—H17A109.2
C1—C6—H6120.5C18—C17—H17A109.2
C8—C7—N1108.64 (18)C16—C17—H17B109.2
C8—C7—C15127.79 (19)C18—C17—H17B109.2
N1—C7—C15123.36 (19)H17A—C17—H17B107.9
C7—C8—C9108.54 (18)C17—C18—H18A109.5
C7—C8—C16122.81 (19)C17—C18—H18B109.5
C9—C8—C16128.6 (2)H18A—C18—H18B109.5
C10—C9—C14118.3 (2)C17—C18—H18C109.5
C10—C9—C8134.9 (2)H18A—C18—H18C109.5
C14—C9—C8106.79 (19)H18B—C18—H18C109.5
C11—C10—C9118.8 (2)C14—N1—C7107.94 (17)
C11—C10—H10120.6C14—N1—S1121.55 (14)
C9—C10—H10120.6C7—N1—S1128.56 (14)
C12—C11—C10121.5 (2)O2—S1—O1120.16 (13)
C12—C11—H11119.3O2—S1—N1106.36 (11)
C10—C11—H11119.3O1—S1—N1106.44 (9)
C13—C12—C11121.6 (2)O2—S1—C1108.93 (11)
C13—C12—H12119.2O1—S1—C1108.79 (11)
C11—C12—H12119.2N1—S1—C1105.11 (10)
C6—C1—C2—C3−1.2 (4)N1—C7—C15—Br1−103.6 (2)
S1—C1—C2—C3173.4 (2)C7—C8—C16—O37.0 (4)
C1—C2—C3—C41.2 (4)C9—C8—C16—O3−171.7 (2)
C2—C3—C4—C5−0.1 (5)C7—C8—C16—C17−171.8 (2)
C3—C4—C5—C6−1.0 (5)C9—C8—C16—C179.5 (3)
C4—C5—C6—C10.9 (5)O3—C16—C17—C18−6.7 (4)
C2—C1—C6—C50.2 (4)C8—C16—C17—C18172.2 (2)
S1—C1—C6—C5−174.4 (2)C13—C14—N1—C7177.2 (2)
N1—C7—C8—C90.5 (2)C9—C14—N1—C7−0.8 (2)
C15—C7—C8—C9175.3 (2)C13—C14—N1—S1−17.4 (3)
N1—C7—C8—C16−178.40 (19)C9—C14—N1—S1164.61 (15)
C15—C7—C8—C16−3.7 (3)C8—C7—N1—C140.2 (2)
C7—C8—C9—C10−179.2 (2)C15—C7—N1—C14−174.9 (2)
C16—C8—C9—C10−0.4 (4)C8—C7—N1—S1−163.90 (16)
C7—C8—C9—C14−1.0 (2)C15—C7—N1—S121.1 (3)
C16—C8—C9—C14177.8 (2)C14—N1—S1—O249.4 (2)
C14—C9—C10—C11−1.1 (3)C7—N1—S1—O2−148.47 (19)
C8—C9—C10—C11176.9 (2)C14—N1—S1—O1178.65 (18)
C9—C10—C11—C120.0 (4)C7—N1—S1—O1−19.2 (2)
C10—C11—C12—C130.8 (4)C14—N1—S1—C1−66.04 (19)
C11—C12—C13—C14−0.5 (4)C7—N1—S1—C196.1 (2)
C12—C13—C14—C9−0.7 (4)C6—C1—S1—O2179.4 (2)
C12—C13—C14—N1−178.4 (2)C2—C1—S1—O24.7 (2)
C10—C9—C14—C131.5 (3)C6—C1—S1—O146.8 (2)
C8—C9—C14—C13−177.0 (2)C2—C1—S1—O1−127.98 (19)
C10—C9—C14—N1179.7 (2)C6—C1—S1—N1−66.9 (2)
C8—C9—C14—N11.1 (2)C2—C1—S1—N1118.35 (19)
C8—C7—C15—Br182.3 (2)
D—H···AD—HH···AD···AD—H···A
C6—H6···Br10.932.893.815 (2)171
C13—H13···O20.932.392.978 (3)121
C15—H15B···O10.972.152.833 (3)126
C2—H2···O3i0.932.593.191 (3)123
C15—H15A···Cg3ii0.972.743.486 (3)134
C18—H18B···Cg2iii0.962.663.616 (3)174
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C6—H6⋯Br10.932.893.815 (2)171
C13—H13⋯O20.932.392.978 (3)121
C15—H15B⋯O10.972.152.833 (3)126
C2—H2⋯O3i 0.932.593.191 (3)123
C15—H15A⋯Cg3ii 0.972.743.486 (3)134
C18—H18B⋯Cg2iii 0.962.663.616 (3)174

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

  6 in total

1.  A short history of SHELX.

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

2.  Synthesis and in vitro anti-hepatitis B virus activities of some ethyl 6-bromo-5-hydroxy-1H-indole-3-carboxylates.

Authors:  Huifang Chai; Yanfang Zhao; Chunshen Zhao; Ping Gong
Journal:  Bioorg Med Chem       Date:  2005-09-23       Impact factor: 3.641

3.  Benzenesulfonamide analogs of fluoroquinolones. Antibacterial activity and QSAR studies.

Authors:  M J Nieto; F L Alovero; R H Manzo; Maria R Mazzieri
Journal:  Eur J Med Chem       Date:  2005-04       Impact factor: 6.514

4.  3-Bromo-meth-yl-2-chloro-meth-yl-1-phenyl-sulfon-yl-1H-indole.

Authors:  G Chakkaravarthi; V Dhayalan; A K Mohanakrishnan; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-03-29

5.  (4-Bromo-phen-yl)(1-phenyl-sulfonyl-1H-indol-2-yl)methanone.

Authors:  G Chakkaravarthi; R Panchatcharam; V Dhayalan; A K Mohanakrishnan; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-30

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  1 in total

1.  Crystal structure of (2-methyl-1-phenyl-sulfon-yl-1H-indol-3-yl)(phen-yl)methanone.

Authors:  M Umadevi; V Saravanan; R Yamuna; A K Mohanakrishnan; G Chakkaravarthi
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-03
  1 in total

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