Literature DB >> 21583636

5-Chloro-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

Hong Dae Choi, Pil Ja Seo, Byeng Wha Son, Uk Lee.   

Abstract

In the title compound, C(20)H(13)ClO(2)S, the O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment; the S-bound phenyl ring is nearly perpendicular to this plane [80.87 (5)°]. The phenyl ring in the 2-position is rotated out of the benzofuran plane, making a dihedral angle of 17.43 (7)°. The crystal structure features π-π inter-actions between the phenyl ring and the furyl ring of a neighbouring benzofuran system [centroid-centroid distance = 3.886 (2) Å].

Entities:  

Year:  2009        PMID： 21583636      PMCID： PMC2977298          DOI： 10.1107/S1600536809028153

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


Related literature

For the crystal structures of similar 2-phenyl-3-phenyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a ▶,b ▶). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Twyman & Allsop (1999 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); von Reuss & König (2004 ▶).

Experimental

Crystal data

C20H13ClO2S M = 352.81 Triclinic, a = 8.2726 (5) Å b = 9.4111 (5) Å c = 11.3811 (6) Å α = 73.360 (1)° β = 81.630 (1)° γ = 70.757 (1)° V = 800.25 (8) Å3 Z = 2 Mo Kα radiation μ = 0.38 mm−1 T = 273 K 0.24 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.915, T max = 0.963 6930 measured reflections 3428 independent reflections 2843 reflections with I > 2σ(I) R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.093 S = 1.06 3428 reflections 217 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.32 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028153/ng2614sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028153/ng2614Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H13ClO2SZ = 2
Mr = 352.81F(000) = 364
Triclinic, P1Dx = 1.464 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2726 (5) ÅCell parameters from 4091 reflections
b = 9.4111 (5) Åθ = 2.4–27.4°
c = 11.3811 (6) ŵ = 0.38 mm−1
α = 73.360 (1)°T = 273 K
β = 81.630 (1)°Block, colorless
γ = 70.757 (1)°0.24 × 0.15 × 0.10 mm
V = 800.25 (8) Å3
Bruker SMART CCD diffractometer3428 independent reflections
Radiation source: fine-focus sealed tube2843 reflections with I > 2σ(I)
graphiteRint = 0.016
Detector resolution: 10.0 pixels mm-1θmax = 27.0°, θmin = 1.9°
φ and ω scansh = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)k = −11→11
Tmin = 0.915, Tmax = 0.963l = −14→14
6930 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: difference Fourier map
wR(F2) = 0.093H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0423P)2 + 0.2959P] where P = (Fo2 + 2Fc2)/3
3428 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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 > 2sigma(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
S0.60764 (5)0.10727 (5)0.36530 (4)0.03141 (12)
Cl1.01634 (7)0.23915 (6)−0.11687 (4)0.04741 (15)
O10.50587 (16)0.56115 (13)0.20476 (11)0.0353 (3)
O20.78018 (15)0.00894 (15)0.33104 (13)0.0442 (3)
C10.5863 (2)0.29999 (19)0.27413 (15)0.0299 (4)
C20.6787 (2)0.33818 (19)0.15726 (15)0.0308 (4)
C30.7989 (2)0.2542 (2)0.08331 (16)0.0336 (4)
H30.83570.14600.10470.040*
C40.8610 (2)0.3395 (2)−0.02336 (17)0.0368 (4)
C50.8064 (3)0.5023 (2)−0.05899 (17)0.0415 (4)
H50.85170.5545−0.13170.050*
C60.6860 (3)0.5857 (2)0.01297 (17)0.0401 (4)
H60.64760.6939−0.00940.048*
C70.6246 (2)0.5006 (2)0.12049 (16)0.0331 (4)
C80.4853 (2)0.4365 (2)0.29930 (15)0.0314 (4)
C90.3623 (2)0.4786 (2)0.39888 (16)0.0325 (4)
C100.3580 (3)0.3731 (2)0.51308 (17)0.0391 (4)
H100.43470.27300.52700.047*
C110.2402 (3)0.4167 (2)0.60561 (18)0.0435 (5)
H110.23820.34550.68140.052*
C120.1258 (3)0.5644 (3)0.58682 (19)0.0465 (5)
H120.04670.59270.64940.056*
C130.1293 (3)0.6706 (3)0.4743 (2)0.0515 (5)
H130.05270.77070.46120.062*
C140.2462 (2)0.6280 (2)0.38153 (19)0.0445 (5)
H140.24770.70010.30620.053*
C150.4533 (2)0.07047 (18)0.29161 (15)0.0286 (3)
C160.5052 (2)−0.0090 (2)0.20082 (17)0.0384 (4)
H160.6205−0.04220.17560.046*
C170.3826 (3)−0.0381 (2)0.14814 (19)0.0467 (5)
H170.4156−0.09060.08650.056*
C180.2127 (3)0.0101 (2)0.1865 (2)0.0482 (5)
H180.1313−0.00900.14980.058*
C190.1615 (2)0.0868 (2)0.2791 (2)0.0444 (5)
H190.04640.11770.30530.053*
C200.2819 (2)0.1173 (2)0.33250 (17)0.0352 (4)
H200.24880.16840.39500.042*
U11U22U33U12U13U23
S0.0263 (2)0.0282 (2)0.0325 (2)−0.00846 (16)−0.00388 (16)0.00459 (16)
Cl0.0486 (3)0.0557 (3)0.0388 (3)−0.0223 (2)0.0101 (2)−0.0119 (2)
O10.0398 (7)0.0282 (6)0.0336 (7)−0.0129 (5)−0.0012 (5)0.0010 (5)
O20.0248 (6)0.0357 (7)0.0569 (9)−0.0031 (5)−0.0028 (6)0.0047 (6)
C10.0275 (8)0.0290 (8)0.0309 (9)−0.0122 (7)−0.0048 (7)0.0017 (7)
C20.0285 (8)0.0323 (9)0.0303 (8)−0.0141 (7)−0.0056 (7)0.0017 (7)
C30.0313 (9)0.0341 (9)0.0338 (9)−0.0136 (7)−0.0027 (7)−0.0014 (7)
C40.0339 (9)0.0427 (10)0.0338 (9)−0.0160 (8)−0.0011 (7)−0.0051 (8)
C50.0477 (11)0.0449 (11)0.0312 (9)−0.0245 (9)0.0013 (8)0.0017 (8)
C60.0480 (11)0.0323 (9)0.0368 (10)−0.0185 (8)−0.0035 (8)0.0041 (8)
C70.0335 (9)0.0327 (9)0.0311 (9)−0.0136 (7)−0.0034 (7)−0.0001 (7)
C80.0316 (9)0.0312 (9)0.0303 (9)−0.0150 (7)−0.0063 (7)0.0026 (7)
C90.0312 (9)0.0331 (9)0.0339 (9)−0.0138 (7)−0.0043 (7)−0.0039 (7)
C100.0450 (10)0.0333 (9)0.0360 (10)−0.0122 (8)−0.0019 (8)−0.0039 (8)
C110.0494 (11)0.0456 (11)0.0334 (10)−0.0181 (9)0.0022 (8)−0.0047 (8)
C120.0405 (11)0.0521 (12)0.0458 (11)−0.0154 (9)0.0082 (9)−0.0147 (9)
C130.0420 (11)0.0415 (11)0.0579 (13)−0.0026 (9)0.0036 (10)−0.0075 (10)
C140.0393 (10)0.0386 (10)0.0432 (11)−0.0077 (8)0.0002 (8)0.0024 (8)
C150.0277 (8)0.0218 (8)0.0300 (8)−0.0077 (6)−0.0005 (6)0.0025 (6)
C160.0398 (10)0.0278 (9)0.0408 (10)−0.0072 (7)0.0059 (8)−0.0060 (7)
C170.0639 (14)0.0327 (10)0.0452 (11)−0.0148 (9)−0.0050 (10)−0.0115 (8)
C180.0533 (12)0.0337 (10)0.0619 (13)−0.0165 (9)−0.0204 (10)−0.0063 (9)
C190.0290 (9)0.0413 (11)0.0610 (13)−0.0122 (8)−0.0040 (9)−0.0075 (9)
C200.0297 (9)0.0335 (9)0.0398 (10)−0.0094 (7)0.0006 (7)−0.0069 (8)
S—O21.4898 (13)C10—C111.383 (3)
S—C11.7782 (16)C10—H100.9300
S—C151.7953 (17)C11—C121.376 (3)
Cl—C41.7471 (19)C11—H110.9300
O1—C71.371 (2)C12—C131.384 (3)
O1—C81.3850 (19)C12—H120.9300
C1—C81.365 (2)C13—C141.378 (3)
C1—C21.447 (2)C13—H130.9300
C2—C31.393 (2)C14—H140.9300
C2—C71.396 (2)C15—C161.383 (3)
C3—C41.384 (2)C15—C201.391 (2)
C3—H30.9300C16—C171.385 (3)
C4—C51.400 (3)C16—H160.9300
C5—C61.376 (3)C17—C181.374 (3)
C5—H50.9300C17—H170.9300
C6—C71.386 (2)C18—C191.384 (3)
C6—H60.9300C18—H180.9300
C8—C91.460 (2)C19—C201.382 (3)
C9—C141.395 (3)C19—H190.9300
C9—C101.395 (2)C20—H200.9300
O2—S—C1106.48 (8)C11—C10—H10119.8
O2—S—C15107.16 (8)C9—C10—H10119.8
C1—S—C1597.09 (7)C12—C11—C10120.71 (18)
C7—O1—C8106.97 (13)C12—C11—H11119.6
C8—C1—C2107.66 (14)C10—C11—H11119.6
C8—C1—S127.92 (13)C11—C12—C13119.62 (19)
C2—C1—S124.42 (13)C11—C12—H12120.2
C3—C2—C7119.65 (15)C13—C12—H12120.2
C3—C2—C1135.69 (16)C14—C13—C12120.05 (19)
C7—C2—C1104.66 (15)C14—C13—H13120.0
C4—C3—C2116.86 (16)C12—C13—H13120.0
C4—C3—H3121.6C13—C14—C9121.03 (18)
C2—C3—H3121.6C13—C14—H14119.5
C3—C4—C5122.95 (18)C9—C14—H14119.5
C3—C4—Cl118.45 (15)C16—C15—C20121.14 (17)
C5—C4—Cl118.60 (14)C16—C15—S120.62 (13)
C6—C5—C4120.37 (16)C20—C15—S118.17 (13)
C6—C5—H5119.8C15—C16—C17118.89 (18)
C4—C5—H5119.8C15—C16—H16120.6
C5—C6—C7116.83 (17)C17—C16—H16120.6
C5—C6—H6121.6C18—C17—C16120.34 (19)
C7—C6—H6121.6C18—C17—H17119.8
O1—C7—C6125.88 (16)C16—C17—H17119.8
O1—C7—C2110.78 (14)C17—C18—C19120.68 (19)
C6—C7—C2123.33 (17)C17—C18—H18119.7
C1—C8—O1109.91 (15)C19—C18—H18119.7
C1—C8—C9135.11 (15)C20—C19—C18119.80 (19)
O1—C8—C9114.96 (15)C20—C19—H19120.1
C14—C9—C10118.28 (17)C18—C19—H19120.1
C14—C9—C8119.98 (16)C19—C20—C15119.13 (18)
C10—C9—C8121.73 (16)C19—C20—H20120.4
C11—C10—C9120.32 (18)C15—C20—H20120.4
O2—S—C1—C8−154.75 (16)C7—O1—C8—C1−1.18 (18)
C15—S—C1—C894.95 (17)C7—O1—C8—C9180.00 (14)
O2—S—C1—C224.56 (16)C1—C8—C9—C14−162.7 (2)
C15—S—C1—C2−85.74 (15)O1—C8—C9—C1415.7 (2)
C8—C1—C2—C3179.49 (19)C1—C8—C9—C1018.0 (3)
S—C1—C2—C30.1 (3)O1—C8—C9—C10−163.57 (16)
C8—C1—C2—C70.36 (18)C14—C9—C10—C110.5 (3)
S—C1—C2—C7−179.07 (12)C8—C9—C10—C11179.81 (17)
C7—C2—C3—C41.3 (2)C9—C10—C11—C12−0.1 (3)
C1—C2—C3—C4−177.78 (18)C10—C11—C12—C13−0.3 (3)
C2—C3—C4—C5−1.0 (3)C11—C12—C13—C140.3 (3)
C2—C3—C4—Cl178.31 (13)C12—C13—C14—C90.0 (3)
C3—C4—C5—C60.2 (3)C10—C9—C14—C13−0.5 (3)
Cl—C4—C5—C6−179.13 (15)C8—C9—C14—C13−179.77 (19)
C4—C5—C6—C70.4 (3)O2—S—C15—C16−12.69 (15)
C8—O1—C7—C6−178.23 (17)C1—S—C15—C1697.05 (14)
C8—O1—C7—C21.43 (18)O2—S—C15—C20164.24 (13)
C5—C6—C7—O1179.52 (17)C1—S—C15—C20−86.02 (14)
C5—C6—C7—C2−0.1 (3)C20—C15—C16—C171.7 (3)
C3—C2—C7—O1179.59 (14)S—C15—C16—C17178.56 (13)
C1—C2—C7—O1−1.11 (19)C15—C16—C17—C18−0.6 (3)
C3—C2—C7—C6−0.7 (3)C16—C17—C18—C19−0.7 (3)
C1—C2—C7—C6178.56 (17)C17—C18—C19—C200.9 (3)
C2—C1—C8—O10.50 (19)C18—C19—C20—C150.2 (3)
S—C1—C8—O1179.91 (12)C16—C15—C20—C19−1.6 (2)
C2—C1—C8—C9178.98 (18)S—C15—C20—C19−178.46 (13)
S—C1—C8—C9−1.6 (3)
  6 in total

1.  Inhibition of fibril formation in beta-amyloid peptide by a novel series of benzofurans.

Authors:  D R Howlett; A E Perry; F Godfrey; J E Swatton; K H Jennings; C Spitzfaden; H Wadsworth; S J Wood; R E Markwell
Journal:  Biochem J       Date:  1999-05-15       Impact factor: 3.857

2.  Benzofurans and another constituent from seeds of Styrax officinalis.

Authors:  Yurdanur Yayla Akgul; Huseyin Anil
Journal:  Phytochemistry       Date:  2003-08       Impact factor: 4.072

3.  A short history of SHELX.

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

4.  5-Iodo-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-11

5.  5-Chloro-7-methyl-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-04

6.  Corsifurans A-C, 2-arylbenzofurans of presumed stilbenoid origin from Corsinia coriandrina (Hepaticae).

Authors:  Stephan H von Reuss; Wilfried A König
Journal:  Phytochemistry       Date:  2004-12       Impact factor: 4.072
  6 in total
  3 in total

1.  5-Bromo-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-03

2.  5-Chloro-2-(4-fluoro-phen-yl)-3-phenyl-sulfinyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-26

3.  2-(4-Bromo-phen-yl)-5-fluoro-3-phenyl-sulfinyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-31
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.