Literature DB >> 22065828

3-(3-Chloro-phenyl-sulfon-yl)-2,5-dimethyl-1-benzofuran.

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

Abstract

In the title molecule, C(16)H(13)ClO(3)S, the 3-chloro-phenyl ring makes a dihedral angle of 76.30 (5)° with the mean plane of the benzofuran fragment. In the crystal, pairs of inter-molecular C-H⋯π inter-actions link the mol-ecules into inversion dimers.

Entities:  

Year:  2011        PMID： 22065828      PMCID： PMC3201520          DOI： 10.1107/S1600536811035720

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


Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For structural studies of 3-(4-chloro­phenyl­sulfon­yl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C16H13ClO3S M = 320.77 Triclinic, a = 8.1000 (4) Å b = 8.8622 (5) Å c = 10.6898 (6) Å α = 84.023 (3)° β = 81.514 (3)° γ = 72.378 (3)° V = 721.90 (7) Å3 Z = 2 Mo Kα radiation μ = 0.42 mm−1 T = 173 K 0.28 × 0.27 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.579, T max = 0.746 13538 measured reflections 3622 independent reflections 2951 reflections with I > 2σ(I) R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.110 S = 1.05 3622 reflections 192 parameters H-atom parameters constrained Δρmax = 0.39 e Å−3 Δρmin = −0.40 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) I. DOI: 10.1107/S1600536811035720/qm2026sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035720/qm2026Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811035720/qm2026Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H13ClO3SZ = 2
Mr = 320.77F(000) = 332
Triclinic, P1Dx = 1.476 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1000 (4) ÅCell parameters from 5186 reflections
b = 8.8622 (5) Åθ = 2.4–27.9°
c = 10.6898 (6) ŵ = 0.42 mm−1
α = 84.023 (3)°T = 173 K
β = 81.514 (3)°Block, colourless
γ = 72.378 (3)°0.28 × 0.27 × 0.19 mm
V = 721.90 (7) Å3
Bruker SMART APEXII CCD diffractometer3622 independent reflections
Radiation source: rotating anode2951 reflections with I > 2σ(I)
graphite multilayerRint = 0.051
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 1.9°
φ and ω scansh = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −11→11
Tmin = 0.579, Tmax = 0.746l = −14→14
13538 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)] = 0.040Hydrogen site location: difference Fourier map
wR(F2) = 0.110H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0497P)2 + 0.243P] where P = (Fo2 + 2Fc2)/3
3622 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.40 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
S10.33167 (5)0.43504 (5)0.29715 (4)0.02475 (13)
Cl1−0.08568 (7)0.78553 (6)−0.04210 (5)0.04248 (16)
O10.49244 (16)−0.00637 (14)0.20581 (12)0.0310 (3)
O20.45023 (15)0.49763 (14)0.20924 (13)0.0328 (3)
O30.31247 (17)0.46293 (15)0.42888 (12)0.0324 (3)
C10.3859 (2)0.23236 (19)0.28520 (16)0.0239 (3)
C20.3302 (2)0.12036 (19)0.37751 (16)0.0242 (3)
C30.2342 (2)0.1260 (2)0.49708 (16)0.0272 (4)
H30.18720.22330.53720.033*
C40.2087 (2)−0.0133 (2)0.55658 (17)0.0298 (4)
C50.2811 (2)−0.1561 (2)0.49675 (19)0.0342 (4)
H50.2626−0.25050.53890.041*
C60.3782 (2)−0.1647 (2)0.3793 (2)0.0341 (4)
H60.4273−0.26210.33950.041*
C70.3998 (2)−0.0244 (2)0.32300 (17)0.0274 (4)
C80.4815 (2)0.1509 (2)0.18512 (17)0.0273 (4)
C90.1031 (3)−0.0119 (3)0.68477 (19)0.0404 (5)
H9A0.11400.07300.73190.061*
H9B0.1462−0.11430.73160.061*
H9C−0.01980.00630.67440.061*
C100.5727 (2)0.1939 (2)0.06278 (18)0.0367 (4)
H10A0.53430.30930.04590.055*
H10B0.54550.1426−0.00520.055*
H10C0.69890.15840.06650.055*
C110.1232 (2)0.51080 (19)0.24554 (15)0.0241 (3)
C12−0.0193 (2)0.4771 (2)0.31850 (17)0.0287 (4)
H12−0.00560.41490.39630.034*
C13−0.1810 (2)0.5353 (2)0.27665 (18)0.0326 (4)
H13−0.27890.51090.32500.039*
C14−0.2017 (2)0.6286 (2)0.16502 (17)0.0313 (4)
H14−0.31330.66830.13620.038*
C15−0.0585 (2)0.6636 (2)0.09564 (17)0.0290 (4)
C160.1054 (2)0.6038 (2)0.13328 (16)0.0277 (4)
H160.20370.62590.08350.033*
U11U22U33U12U13U23
S10.0225 (2)0.0215 (2)0.0316 (2)−0.00858 (15)−0.00493 (16)0.00078 (16)
Cl10.0428 (3)0.0451 (3)0.0349 (3)−0.0092 (2)−0.0093 (2)0.0141 (2)
O10.0274 (6)0.0253 (6)0.0376 (7)−0.0053 (5)0.0013 (5)−0.0050 (5)
O20.0245 (6)0.0294 (7)0.0460 (8)−0.0130 (5)−0.0032 (5)0.0051 (5)
O30.0383 (7)0.0286 (6)0.0335 (7)−0.0114 (5)−0.0106 (5)−0.0027 (5)
C10.0210 (7)0.0221 (7)0.0294 (8)−0.0071 (6)−0.0048 (6)0.0008 (6)
C20.0198 (7)0.0225 (8)0.0315 (9)−0.0071 (6)−0.0072 (6)0.0010 (6)
C30.0259 (8)0.0260 (8)0.0300 (9)−0.0075 (6)−0.0059 (7)0.0003 (7)
C40.0257 (8)0.0330 (9)0.0325 (9)−0.0115 (7)−0.0093 (7)0.0067 (7)
C50.0314 (9)0.0254 (9)0.0469 (11)−0.0114 (7)−0.0093 (8)0.0083 (8)
C60.0310 (9)0.0222 (8)0.0495 (12)−0.0075 (7)−0.0062 (8)−0.0024 (8)
C70.0219 (8)0.0256 (8)0.0343 (9)−0.0062 (6)−0.0040 (7)−0.0008 (7)
C80.0218 (8)0.0256 (8)0.0339 (9)−0.0059 (6)−0.0053 (7)0.0001 (7)
C90.0420 (11)0.0465 (11)0.0343 (10)−0.0199 (9)−0.0036 (8)0.0096 (9)
C100.0323 (9)0.0402 (10)0.0331 (10)−0.0079 (8)0.0025 (8)0.0003 (8)
C110.0222 (8)0.0223 (8)0.0273 (8)−0.0061 (6)−0.0024 (6)−0.0010 (6)
C120.0264 (8)0.0293 (9)0.0288 (9)−0.0083 (7)−0.0019 (7)0.0047 (7)
C130.0237 (8)0.0375 (10)0.0349 (10)−0.0095 (7)0.0001 (7)0.0023 (8)
C140.0241 (8)0.0338 (9)0.0330 (9)−0.0034 (7)−0.0054 (7)−0.0011 (7)
C150.0307 (9)0.0263 (8)0.0270 (9)−0.0046 (7)−0.0045 (7)0.0016 (7)
C160.0264 (8)0.0257 (8)0.0298 (9)−0.0079 (7)−0.0008 (7)0.0012 (7)
S1—O31.4328 (13)C6—H60.9500
S1—O21.4355 (12)C8—C101.478 (2)
S1—C11.7289 (17)C9—H9A0.9800
S1—C111.7659 (17)C9—H9B0.9800
Cl1—C151.7334 (18)C9—H9C0.9800
O1—C81.366 (2)C10—H10A0.9800
O1—C71.383 (2)C10—H10B0.9800
C1—C81.357 (2)C10—H10C0.9800
C1—C21.449 (2)C11—C161.383 (2)
C2—C71.387 (2)C11—C121.387 (2)
C2—C31.392 (2)C12—C131.377 (3)
C3—C41.386 (2)C12—H120.9500
C3—H30.9500C13—C141.380 (3)
C4—C51.401 (3)C13—H130.9500
C4—C91.504 (3)C14—C151.381 (2)
C5—C61.376 (3)C14—H140.9500
C5—H50.9500C15—C161.376 (2)
C6—C71.373 (3)C16—H160.9500
O3—S1—O2119.46 (8)C4—C9—H9A109.5
O3—S1—C1107.56 (8)C4—C9—H9B109.5
O2—S1—C1109.13 (8)H9A—C9—H9B109.5
O3—S1—C11107.49 (8)C4—C9—H9C109.5
O2—S1—C11107.47 (8)H9A—C9—H9C109.5
C1—S1—C11104.80 (8)H9B—C9—H9C109.5
C8—O1—C7106.97 (13)C8—C10—H10A109.5
C8—C1—C2107.83 (15)C8—C10—H10B109.5
C8—C1—S1126.08 (13)H10A—C10—H10B109.5
C2—C1—S1126.02 (12)C8—C10—H10C109.5
C7—C2—C3119.05 (16)H10A—C10—H10C109.5
C7—C2—C1104.37 (15)H10B—C10—H10C109.5
C3—C2—C1136.58 (16)C16—C11—C12121.36 (16)
C4—C3—C2118.71 (16)C16—C11—S1119.09 (12)
C4—C3—H3120.6C12—C11—S1119.55 (13)
C2—C3—H3120.6C13—C12—C11119.07 (16)
C3—C4—C5119.84 (16)C13—C12—H12120.5
C3—C4—C9120.42 (17)C11—C12—H12120.5
C5—C4—C9119.74 (17)C12—C13—C14120.52 (16)
C6—C5—C4122.43 (17)C12—C13—H13119.7
C6—C5—H5118.8C14—C13—H13119.7
C4—C5—H5118.8C13—C14—C15119.29 (17)
C7—C6—C5116.06 (17)C13—C14—H14120.4
C7—C6—H6122.0C15—C14—H14120.4
C5—C6—H6122.0C16—C15—C14121.53 (16)
C6—C7—O1125.54 (16)C16—C15—Cl1119.16 (14)
C6—C7—C2123.90 (16)C14—C15—Cl1119.31 (14)
O1—C7—C2110.56 (15)C15—C16—C11118.19 (16)
C1—C8—O1110.26 (15)C15—C16—H16120.9
C1—C8—C10134.82 (17)C11—C16—H16120.9
O1—C8—C10114.92 (15)
O3—S1—C1—C8−151.41 (16)C1—C2—C7—O10.08 (19)
O2—S1—C1—C8−20.43 (19)C2—C1—C8—O1−0.2 (2)
C11—S1—C1—C894.41 (17)S1—C1—C8—O1−177.39 (12)
O3—S1—C1—C231.89 (17)C2—C1—C8—C10179.7 (2)
O2—S1—C1—C2162.86 (14)S1—C1—C8—C102.5 (3)
C11—S1—C1—C2−82.29 (16)C7—O1—C8—C10.2 (2)
C8—C1—C2—C70.06 (19)C7—O1—C8—C10−179.65 (15)
S1—C1—C2—C7177.27 (13)O3—S1—C11—C16133.45 (14)
C8—C1—C2—C3179.0 (2)O2—S1—C11—C163.68 (16)
S1—C1—C2—C3−3.8 (3)C1—S1—C11—C16−112.32 (14)
C7—C2—C3—C4−1.3 (3)O3—S1—C11—C12−46.03 (16)
C1—C2—C3—C4179.93 (18)O2—S1—C11—C12−175.80 (14)
C2—C3—C4—C50.9 (3)C1—S1—C11—C1268.19 (16)
C2—C3—C4—C9−178.90 (17)C16—C11—C12—C131.3 (3)
C3—C4—C5—C6−0.1 (3)S1—C11—C12—C13−179.25 (14)
C9—C4—C5—C6179.68 (18)C11—C12—C13—C14−1.4 (3)
C4—C5—C6—C7−0.3 (3)C12—C13—C14—C15−0.2 (3)
C5—C6—C7—O1179.85 (17)C13—C14—C15—C161.9 (3)
C5—C6—C7—C2−0.1 (3)C13—C14—C15—Cl1−178.12 (15)
C8—O1—C7—C6179.81 (18)C14—C15—C16—C11−2.0 (3)
C8—O1—C7—C2−0.20 (19)Cl1—C15—C16—C11178.02 (13)
C3—C2—C7—C60.9 (3)C12—C11—C16—C150.4 (3)
C1—C2—C7—C6−179.93 (17)S1—C11—C16—C15−179.09 (13)
C3—C2—C7—O1−179.07 (15)
Cg is the centroid of the C2–C7 benzene ring.
D—H···AD—HH···AD···AD—H···A
C9—H9C···Cgi0.982.733.663 (2)159.
Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C9—H9C⋯Cgi0.982.733.663 (2)159

Symmetry code: (i) .

  8 in total

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

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

2.  A new structural alternative in benzo[b]furans for antimicrobial activity.

Authors:  M Wahab Khan; M Jahangir Alam; M A Rashid; R Chowdhury
Journal:  Bioorg Med Chem       Date:  2005-08-15       Impact factor: 3.641

3.  A short history of SHELX.

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

4.  Artoindonesianins X and Y, two isoprenylated 2-arylbenzofurans, from Artocarpus fretessi (Moraceae).

Authors:  Nunuk H Soekamto; Sjamsul A Achmad; Emilio L Ghisalberti; Euis H Hakim; Yana M Syah
Journal:  Phytochemistry       Date:  2003-10       Impact factor: 4.072

5.  Synthesis of potent antitumor and antiviral benzofuran derivatives.

Authors:  Shadia A Galal; Amira S Abd El-All; Mohamed M Abdallah; Hoda I El-Diwani
Journal:  Bioorg Med Chem Lett       Date:  2009-03-21       Impact factor: 2.823

6.  Antibacterial and antifungal activity of cicerfuran and related 2-arylbenzofurans and stilbenes.

Authors:  Shazia N Aslam; Philip C Stevenson; Tetsuo Kokubun; David R Hall
Journal:  Microbiol Res       Date:  2007-04-05       Impact factor: 5.415

7.  3-(4-Chloro-phenyl-sulfon-yl)-2,5-dimethyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-06

8.  3-(4-Chloro-phenyl-sulfon-yl)-5-isopropyl-2-methyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-29
  8 in total

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