Literature DB >> 24454226

(Z)-3-(1-Chloro-prop-1-en-yl)-2-methyl-1-phenyl-sulfonyl-1H-indole.

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

Abstract

In the title compound, C18H16ClNO2S, the indole ring system forms a dihedral angle of 75.07 (8)° with the phenyl ring. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming a chain along [10-1]. C-H⋯π inter-actions are also observed, leading to a three-dimensional network.

Entities:  

Year:  2013        PMID： 24454226      PMCID： PMC3885050          DOI： 10.1107/S1600536813030730

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


Related literature

For the biological activity of indole derivatives, see: Okabe & Adachi (1998 ▶); Schollmeyer et al. (1995 ▶). For related structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C18H16ClNO2S M = 345.83 Monoclinic, a = 12.5204 (10) Å b = 10.4962 (7) Å c = 12.983 (1) Å β = 98.892 (2)° V = 1685.7 (2) Å3 Z = 4 Mo Kα radiation μ = 0.36 mm−1 T = 295 K 0.28 × 0.24 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.906, T max = 0.938 20036 measured reflections 4705 independent reflections 3357 reflections with I > 2σ(I) R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.118 S = 1.03 4705 reflections 210 parameters H-atom parameters constrained Δρmax = 0.26 e Å−3 Δρmin = −0.38 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/S1600536813030730/is5320sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030730/is5320Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813030730/is5320Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H16ClNO2SF(000) = 720
Mr = 345.83Dx = 1.363 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6694 reflections
a = 12.5204 (10) Åθ = 2.1–27.9°
b = 10.4962 (7) ŵ = 0.36 mm−1
c = 12.983 (1) ÅT = 295 K
β = 98.892 (2)°Block, colourless
V = 1685.7 (2) Å30.28 × 0.24 × 0.18 mm
Z = 4
Bruker Kappa APEXII diffractometer4705 independent reflections
Radiation source: fine-focus sealed tube3357 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω and φ scanθmax = 29.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −17→17
Tmin = 0.906, Tmax = 0.938k = −14→8
20036 measured reflectionsl = −17→17
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.048P)2 + 0.5443P] where P = (Fo2 + 2Fc2)/3
4705 reflections(Δ/σ)max < 0.001
210 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
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 > σ(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.
xyzUiso*/Ueq
C10.59725 (13)0.25271 (15)0.25702 (12)0.0409 (4)
C20.61126 (16)0.36677 (19)0.20771 (15)0.0538 (4)
H20.67910.40460.21400.065*
C30.52304 (19)0.4234 (2)0.14909 (17)0.0662 (6)
H30.53100.50060.11590.079*
C40.42317 (19)0.3664 (2)0.13940 (17)0.0677 (6)
H40.36410.40480.09900.081*
C50.41016 (17)0.2544 (2)0.18844 (18)0.0658 (6)
H50.34210.21700.18170.079*
C60.49712 (15)0.19547 (18)0.24823 (16)0.0532 (4)
H60.48830.11880.28180.064*
C70.64323 (12)0.27161 (16)0.50763 (12)0.0387 (3)
C80.56922 (15)0.17868 (18)0.52523 (15)0.0506 (4)
H80.56710.09970.49250.061*
C90.49922 (17)0.2087 (2)0.59334 (17)0.0616 (5)
H90.44850.14870.60680.074*
C100.50223 (17)0.3261 (2)0.64240 (17)0.0643 (6)
H100.45340.34350.68770.077*
C110.57600 (16)0.4172 (2)0.62521 (15)0.0548 (5)
H110.57780.49580.65850.066*
C120.64785 (13)0.38933 (16)0.55705 (13)0.0402 (4)
C130.73423 (13)0.46134 (16)0.52297 (13)0.0404 (4)
C140.77940 (13)0.39021 (16)0.45452 (13)0.0403 (4)
C150.87719 (15)0.4191 (2)0.40629 (17)0.0599 (5)
H15A0.90960.49670.43520.090*
H15B0.85680.42870.33230.090*
H15C0.92820.35060.42030.090*
C160.77116 (14)0.58673 (17)0.56392 (14)0.0474 (4)
C170.7704 (2)0.6928 (2)0.51122 (18)0.0678 (6)
H170.74630.68810.43990.081*
C180.8047 (3)0.8218 (2)0.5545 (2)0.0989 (10)
H18A0.75730.88560.51980.148*
H18B0.87750.83860.54340.148*
H18C0.80140.82340.62780.148*
N10.72580 (10)0.26962 (13)0.44364 (10)0.0389 (3)
O10.68061 (11)0.05793 (12)0.36391 (11)0.0580 (3)
O20.80267 (11)0.20029 (14)0.28742 (11)0.0606 (4)
S10.70889 (3)0.18303 (4)0.33504 (3)0.04316 (13)
Cl10.81805 (5)0.58714 (5)0.69822 (4)0.07334 (19)
U11U22U33U12U13U23
C10.0475 (9)0.0363 (9)0.0386 (8)0.0013 (7)0.0059 (7)−0.0079 (6)
C20.0581 (11)0.0478 (11)0.0547 (11)−0.0050 (8)0.0061 (9)0.0042 (8)
C30.0830 (16)0.0484 (12)0.0628 (13)0.0038 (10)−0.0028 (11)0.0088 (9)
C40.0729 (14)0.0563 (13)0.0647 (13)0.0113 (11)−0.0182 (11)−0.0081 (10)
C50.0532 (12)0.0609 (14)0.0768 (15)−0.0059 (9)−0.0107 (10)−0.0115 (11)
C60.0562 (11)0.0432 (10)0.0575 (11)−0.0082 (8)0.0008 (9)−0.0047 (8)
C70.0361 (8)0.0442 (9)0.0353 (8)−0.0018 (6)0.0041 (6)0.0017 (6)
C80.0532 (10)0.0487 (11)0.0502 (10)−0.0107 (8)0.0086 (8)0.0016 (8)
C90.0551 (11)0.0723 (14)0.0602 (12)−0.0187 (10)0.0178 (9)0.0050 (10)
C100.0534 (11)0.0863 (16)0.0586 (12)−0.0065 (10)0.0260 (10)−0.0055 (11)
C110.0534 (11)0.0625 (12)0.0507 (11)−0.0006 (9)0.0147 (8)−0.0114 (9)
C120.0381 (8)0.0443 (9)0.0372 (8)−0.0003 (6)0.0030 (6)0.0004 (6)
C130.0393 (8)0.0400 (9)0.0403 (8)−0.0028 (6)0.0009 (6)0.0010 (6)
C140.0367 (8)0.0443 (9)0.0392 (8)−0.0053 (6)0.0032 (6)0.0018 (6)
C150.0452 (10)0.0750 (14)0.0617 (12)−0.0163 (9)0.0151 (9)−0.0058 (10)
C160.0464 (9)0.0449 (10)0.0484 (10)−0.0041 (7)−0.0008 (7)−0.0033 (7)
C170.0869 (16)0.0502 (13)0.0620 (13)−0.0157 (10)−0.0022 (11)0.0037 (9)
C180.147 (3)0.0493 (15)0.094 (2)−0.0298 (15)−0.0015 (18)0.0022 (12)
N10.0374 (7)0.0413 (8)0.0381 (7)−0.0024 (5)0.0059 (5)−0.0021 (5)
O10.0720 (9)0.0340 (7)0.0679 (9)0.0075 (6)0.0105 (7)−0.0009 (6)
O20.0519 (8)0.0711 (10)0.0631 (9)0.0087 (6)0.0228 (6)−0.0116 (7)
S10.0456 (2)0.0383 (2)0.0463 (2)0.00578 (16)0.00928 (17)−0.00582 (17)
Cl10.1009 (4)0.0574 (3)0.0532 (3)−0.0016 (3)−0.0152 (3)−0.0087 (2)
C1—C61.379 (2)C11—C121.387 (2)
C1—C21.382 (2)C11—H110.9300
C1—S11.7541 (17)C12—C131.444 (2)
C2—C31.376 (3)C13—C141.350 (2)
C2—H20.9300C13—C161.467 (2)
C3—C41.374 (3)C14—N11.429 (2)
C3—H30.9300C14—C151.490 (2)
C4—C51.359 (3)C15—H15A0.9600
C4—H40.9300C15—H15B0.9600
C5—C61.382 (3)C15—H15C0.9600
C5—H50.9300C16—C171.306 (3)
C6—H60.9300C16—Cl11.7517 (18)
C7—C81.388 (2)C17—C181.502 (3)
C7—C121.389 (2)C17—H170.9300
C7—N11.4229 (19)C18—H18A0.9600
C8—C91.374 (3)C18—H18B0.9600
C8—H80.9300C18—H18C0.9600
C9—C101.385 (3)N1—S11.6634 (14)
C9—H90.9300O1—S11.4251 (14)
C10—C111.371 (3)O2—S11.4207 (13)
C10—H100.9300
C6—C1—C2121.21 (17)C7—C12—C13107.68 (14)
C6—C1—S1119.95 (14)C14—C13—C12108.79 (15)
C2—C1—S1118.82 (14)C14—C13—C16126.44 (15)
C3—C2—C1118.84 (19)C12—C13—C16124.58 (15)
C3—C2—H2120.6C13—C14—N1108.47 (14)
C1—C2—H2120.6C13—C14—C15128.24 (16)
C4—C3—C2120.3 (2)N1—C14—C15122.86 (15)
C4—C3—H3119.9C14—C15—H15A109.5
C2—C3—H3119.9C14—C15—H15B109.5
C5—C4—C3120.5 (2)H15A—C15—H15B109.5
C5—C4—H4119.8C14—C15—H15C109.5
C3—C4—H4119.8H15A—C15—H15C109.5
C4—C5—C6120.6 (2)H15B—C15—H15C109.5
C4—C5—H5119.7C17—C16—C13126.77 (18)
C6—C5—H5119.7C17—C16—Cl1119.57 (15)
C1—C6—C5118.62 (19)C13—C16—Cl1113.66 (13)
C1—C6—H6120.7C16—C17—C18126.4 (2)
C5—C6—H6120.7C16—C17—H17116.8
C8—C7—C12122.00 (15)C18—C17—H17116.8
C8—C7—N1130.50 (16)C17—C18—H18A109.5
C12—C7—N1107.49 (13)C17—C18—H18B109.5
C9—C8—C7116.92 (18)H18A—C18—H18B109.5
C9—C8—H8121.5C17—C18—H18C109.5
C7—C8—H8121.5H18A—C18—H18C109.5
C8—C9—C10121.70 (18)H18B—C18—H18C109.5
C8—C9—H9119.2C7—N1—C14107.56 (13)
C10—C9—H9119.2C7—N1—S1119.61 (11)
C11—C10—C9121.08 (18)C14—N1—S1124.33 (11)
C11—C10—H10119.5O2—S1—O1119.18 (8)
C9—C10—H10119.5O2—S1—N1107.08 (8)
C10—C11—C12118.48 (18)O1—S1—N1106.54 (8)
C10—C11—H11120.8O2—S1—C1109.51 (8)
C12—C11—H11120.8O1—S1—C1109.14 (8)
C11—C12—C7119.81 (16)N1—S1—C1104.32 (7)
C11—C12—C13132.51 (17)
C6—C1—C2—C30.1 (3)C14—C13—C16—C1766.3 (3)
S1—C1—C2—C3−178.03 (16)C12—C13—C16—C17−119.2 (2)
C1—C2—C3—C4−0.5 (3)C14—C13—C16—Cl1−114.73 (18)
C2—C3—C4—C50.7 (4)C12—C13—C16—Cl159.8 (2)
C3—C4—C5—C6−0.4 (3)C13—C16—C17—C18177.7 (2)
C2—C1—C6—C50.2 (3)Cl1—C16—C17—C18−1.3 (4)
S1—C1—C6—C5178.30 (15)C8—C7—N1—C14−179.54 (17)
C4—C5—C6—C10.0 (3)C12—C7—N1—C14−0.88 (17)
C12—C7—C8—C90.7 (3)C8—C7—N1—S131.1 (2)
N1—C7—C8—C9179.20 (18)C12—C7—N1—S1−150.22 (12)
C7—C8—C9—C10−0.1 (3)C13—C14—N1—C71.30 (18)
C8—C9—C10—C11−0.4 (4)C15—C14—N1—C7174.34 (16)
C9—C10—C11—C120.2 (3)C13—C14—N1—S1148.83 (12)
C10—C11—C12—C70.4 (3)C15—C14—N1—S1−38.1 (2)
C10—C11—C12—C13−179.39 (19)C7—N1—S1—O2179.44 (12)
C8—C7—C12—C11−0.9 (3)C14—N1—S1—O235.51 (15)
N1—C7—C12—C11−179.69 (16)C7—N1—S1—O1−51.99 (14)
C8—C7—C12—C13178.96 (16)C14—N1—S1—O1164.08 (13)
N1—C7—C12—C130.17 (18)C7—N1—S1—C163.40 (14)
C11—C12—C13—C14−179.51 (19)C14—N1—S1—C1−80.53 (14)
C7—C12—C13—C140.65 (19)C6—C1—S1—O2143.30 (15)
C11—C12—C13—C165.2 (3)C2—C1—S1—O2−38.55 (16)
C7—C12—C13—C16−174.67 (15)C6—C1—S1—O111.19 (17)
C12—C13—C14—N1−1.20 (18)C2—C1—S1—O1−170.66 (13)
C16—C13—C14—N1174.01 (15)C6—C1—S1—N1−102.37 (15)
C12—C13—C14—C15−173.75 (18)C2—C1—S1—N175.78 (15)
C16—C13—C14—C151.5 (3)
D—H···AD—HH···AD···AD—H···A
C8—H8···O10.932.392.973 (2)120
C10—H10···O2i0.932.493.364 (2)157
C5—H5···Cg1ii0.932.823.477 (2)128
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C7/C12–C14 ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C8—H8⋯O10.932.392.973 (2)120
C10—H10⋯O2i 0.932.493.364 (2)157
C5—H5⋯Cg1ii 0.932.823.477 (2)128

Symmetry codes: (i) ; (ii) .

  3 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.  (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

3.  Structure validation in chemical crystallography.

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

1.  Crystal structure of (2-bromo-methyl-1-phenyl-sulfonyl-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

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

Authors:  J Kanchanadevi; G Anbalagan; V Saravanan; A K Mohanakrishnan; B Gunasekaran; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-01-15

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

Authors:  C Ramathilagam; P R Umarani; V Saravanan; A K Mohanakrishnan; B Gunasekaran; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-02-15

4.  (E)-1-[2-(2-Nitro-styr-yl)-1-phenyl-sulfonyl-1H-indol-3-yl]propan-1-one.

Authors:  J Kanchanadevi; G Anbalagan; V Saravanan; A K Mohanakrishnan; B Gunasekaran; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-01-15
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.