Literature DB >> 25309201

Crystal structure of 5-chloro-2,7-dimethyl-3-[(4-methyl-phenyl)-sulfon-yl]-1-benzo-furan.

Hong Dae Choi1, Uk Lee2.   

Abstract

In the title compound, C17H15ClO3S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.008 Å] and the 4-methyl-phenyl ring is 77.29 (4)°. In the crystal, mol-ecules are linked by π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.847 (2) Å] and between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.743 (2) Å]. The mol-ecules are stacked along the a-axis direction. In addition, pairs of C-H⋯O hydrogen bonds are observed between inversion-related dimers: these generate R 2 (2)(12) loops.

Entities:  

Keywords:  4-methyl­phen­yl; C—H⋯O hydrogen bonds; benzo­furan; crystal structure; π–π inter­actions

Year:  2014        PMID： 25309201      PMCID： PMC4186162          DOI： 10.1107/S1600536814018339

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


Related literature

For the pharmaceutical properties of benzo­furan compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Howlett et al. (1999 ▶); Khan et al. (2005 ▶); Ono et al. (2002 ▶). For natural products with a benzo­furan ring, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the synthesis of the starting material 5-chloro-2,7-dimethyl-3-(4-methyl­phenyl­sulfan­yl)-1-benzo­furan, see: Choi et al. (1999 ▶). For a related structure, see: Choi et al. (2014 ▶).

Experimental

Crystal data

C17H15ClO3S M = 334.80 Triclinic, a = 8.2757 (2) Å b = 9.6740 (2) Å c = 10.1564 (2) Å α = 76.655 (1)° β = 75.673 (1)° γ = 76.355 (1)° V = 752.64 (3) Å3 Z = 2 Mo Kα radiation μ = 0.40 mm−1 T = 173 K 0.35 × 0.32 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.871, T max = 0.905 14105 measured reflections 3745 independent reflections 3274 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.099 S = 1.05 3745 reflections 202 parameters H-atom parameters constrained Δρmax = 0.34 e Å−3 Δρmin = −0.32 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶; software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814018339/hb7272sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018339/hb7272Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814018339/hb7272Isup3.cml Click here for additional data file. . DOI: 10.1107/S1600536814018339/hb7272fig1.tif The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. Click here for additional data file. x y z x y z x y z x y z x y z . DOI: 10.1107/S1600536814018339/hb7272fig2.tif A view of the C—H⋯O and π⋯π inter­actions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) − x + 1, − y + 1, − z; (ii) − x + 1, − y + 1, − z + 1; (iii) − x, − y + 1, − z + 1; (iv) x + 1, y, z; (v) x + 1, y, z.] CCDC reference: 1018954 Additional supporting information: crystallographic information; 3D view; checkCIF report
C17H15ClO3SZ = 2
Mr = 334.80F(000) = 348
Triclinic, P1Dx = 1.477 Mg m−3
Hall symbol: -P 1Melting point = 469–468 K
a = 8.2757 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.6740 (2) ÅCell parameters from 5796 reflections
c = 10.1564 (2) Åθ = 2.6–28.4°
α = 76.655 (1)°µ = 0.40 mm−1
β = 75.673 (1)°T = 173 K
γ = 76.355 (1)°Block, colourless
V = 752.64 (3) Å30.35 × 0.32 × 0.25 mm
Bruker SMART APEXII CCD diffractometer3745 independent reflections
Radiation source: rotating anode3274 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.023
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 2.1°
φ and ω scansh = −11→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −12→12
Tmin = 0.871, Tmax = 0.905l = −13→13
14105 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)] = 0.035Hydrogen site location: difference Fourier map
wR(F2) = 0.099H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.050P)2 + 0.3424P] where P = (Fo2 + 2Fc2)/3
3745 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.34 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 7.87 (d, J = 8.56 Hz, 2H), 7.68 (s, 1H),7.31 (d, J = 8.24 Hz, 2H), 7.07-7.09 (m, 1H), 2.80 (s, 3H), 2.42 (s, 3H), 2.39 (s, 3H).
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
Cl10.49131 (6)0.18481 (4)0.50226 (5)0.03579 (12)
S10.09180 (5)0.67869 (4)0.15275 (4)0.02306 (11)
O10.06794 (14)0.75353 (12)0.52188 (11)0.0243 (2)
O20.11863 (15)0.52962 (13)0.14105 (12)0.0301 (3)
O3−0.05754 (14)0.77699 (13)0.11729 (12)0.0312 (3)
C10.09965 (19)0.67929 (16)0.32240 (14)0.0219 (3)
C20.19361 (19)0.56512 (16)0.40987 (14)0.0216 (3)
C30.29224 (19)0.42829 (16)0.39832 (15)0.0240 (3)
H30.30990.38780.31790.029*
C40.3628 (2)0.35505 (17)0.51112 (16)0.0259 (3)
C50.3387 (2)0.41057 (18)0.63123 (16)0.0276 (3)
H50.39070.35470.70510.033*
C60.2401 (2)0.54586 (18)0.64457 (15)0.0252 (3)
C70.16990 (19)0.61807 (16)0.53085 (15)0.0224 (3)
C80.02745 (19)0.78847 (17)0.39395 (15)0.0238 (3)
C90.2140 (2)0.6124 (2)0.76979 (16)0.0324 (4)
H9A0.30060.67100.75600.049*
H9B0.22350.53560.85110.049*
H9C0.10100.67380.78410.049*
C10−0.0811 (2)0.93214 (18)0.36327 (17)0.0302 (3)
H10A−0.10290.94750.26990.045*
H10B−0.02331.00740.36910.045*
H10C−0.18910.93680.43050.045*
C110.27059 (19)0.74903 (17)0.05186 (14)0.0230 (3)
C120.4317 (2)0.66660 (18)0.05643 (17)0.0299 (3)
H120.44540.57430.11480.036*
C130.5723 (2)0.72047 (19)−0.02508 (18)0.0325 (4)
H130.68290.6650−0.02140.039*
C140.5538 (2)0.85464 (19)−0.11220 (16)0.0294 (3)
C150.3924 (2)0.93542 (19)−0.11401 (17)0.0339 (4)
H150.37851.0278−0.17230.041*
C160.2502 (2)0.88400 (18)−0.03225 (17)0.0300 (3)
H160.13990.9409−0.03390.036*
C170.7084 (2)0.9091 (2)−0.2026 (2)0.0413 (4)
H17A0.74290.8668−0.28650.062*
H17B0.80140.8811−0.15220.062*
H17C0.68151.0148−0.22790.062*
U11U22U33U12U13U23
Cl10.0358 (2)0.0238 (2)0.0425 (2)−0.00058 (16)−0.00815 (18)−0.00056 (16)
S10.02253 (19)0.0282 (2)0.01904 (17)−0.00402 (14)−0.00553 (13)−0.00488 (13)
O10.0263 (5)0.0257 (5)0.0213 (5)−0.0033 (4)−0.0049 (4)−0.0068 (4)
O20.0349 (6)0.0318 (6)0.0270 (6)−0.0095 (5)−0.0057 (5)−0.0093 (5)
O30.0249 (6)0.0400 (7)0.0274 (6)−0.0017 (5)−0.0096 (5)−0.0038 (5)
C10.0221 (7)0.0248 (7)0.0190 (6)−0.0043 (6)−0.0042 (5)−0.0043 (5)
C20.0217 (7)0.0238 (7)0.0194 (6)−0.0066 (6)−0.0034 (5)−0.0027 (5)
C30.0247 (7)0.0241 (7)0.0231 (7)−0.0058 (6)−0.0035 (6)−0.0043 (6)
C40.0241 (7)0.0220 (7)0.0291 (7)−0.0047 (6)−0.0046 (6)−0.0001 (6)
C50.0288 (8)0.0304 (8)0.0241 (7)−0.0099 (6)−0.0087 (6)0.0019 (6)
C60.0261 (8)0.0307 (8)0.0204 (7)−0.0106 (6)−0.0047 (6)−0.0026 (6)
C70.0220 (7)0.0238 (7)0.0213 (7)−0.0056 (6)−0.0028 (5)−0.0045 (5)
C80.0227 (7)0.0268 (8)0.0218 (7)−0.0054 (6)−0.0038 (5)−0.0043 (6)
C90.0376 (9)0.0400 (10)0.0227 (7)−0.0106 (7)−0.0086 (6)−0.0061 (7)
C100.0296 (8)0.0278 (8)0.0318 (8)0.0006 (6)−0.0078 (6)−0.0073 (6)
C110.0243 (7)0.0269 (8)0.0176 (6)−0.0042 (6)−0.0035 (5)−0.0054 (5)
C120.0282 (8)0.0270 (8)0.0309 (8)−0.0019 (6)−0.0062 (6)−0.0011 (6)
C130.0230 (8)0.0355 (9)0.0353 (9)−0.0001 (7)−0.0034 (6)−0.0074 (7)
C140.0305 (8)0.0351 (9)0.0231 (7)−0.0090 (7)−0.0013 (6)−0.0082 (6)
C150.0366 (9)0.0313 (9)0.0286 (8)−0.0061 (7)−0.0058 (7)0.0033 (7)
C160.0271 (8)0.0309 (8)0.0277 (8)−0.0008 (6)−0.0067 (6)−0.0005 (6)
C170.0350 (10)0.0507 (12)0.0362 (9)−0.0159 (9)0.0027 (7)−0.0069 (8)
Cl1—C41.7452 (16)C9—H9B0.9800
S1—O21.4346 (12)C9—H9C0.9800
S1—O31.4384 (11)C10—H10A0.9800
S1—C11.7417 (14)C10—H10B0.9800
S1—C111.7621 (16)C10—H10C0.9800
O1—C81.3690 (17)C11—C161.384 (2)
O1—C71.3779 (18)C11—C121.388 (2)
C1—C81.357 (2)C12—C131.386 (2)
C1—C21.448 (2)C12—H120.9500
C2—C71.391 (2)C13—C141.391 (2)
C2—C31.395 (2)C13—H130.9500
C3—C41.385 (2)C14—C151.382 (2)
C3—H30.9500C14—C171.507 (2)
C4—C51.396 (2)C15—C161.387 (2)
C5—C61.386 (2)C15—H150.9500
C5—H50.9500C16—H160.9500
C6—C71.388 (2)C17—H17A0.9800
C6—C91.501 (2)C17—H17B0.9800
C8—C101.478 (2)C17—H17C0.9800
C9—H9A0.9800
O2—S1—O3119.70 (7)C6—C9—H9C109.5
O2—S1—C1106.30 (7)H9A—C9—H9C109.5
O3—S1—C1109.53 (7)H9B—C9—H9C109.5
O2—S1—C11107.88 (7)C8—C10—H10A109.5
O3—S1—C11107.90 (7)C8—C10—H10B109.5
C1—S1—C11104.52 (7)H10A—C10—H10B109.5
C8—O1—C7107.01 (11)C8—C10—H10C109.5
C8—C1—C2107.66 (13)H10A—C10—H10C109.5
C8—C1—S1126.70 (12)H10B—C10—H10C109.5
C2—C1—S1125.56 (12)C16—C11—C12120.52 (15)
C7—C2—C3119.58 (13)C16—C11—S1120.29 (12)
C7—C2—C1104.47 (13)C12—C11—S1119.18 (12)
C3—C2—C1135.95 (14)C13—C12—C11119.26 (15)
C4—C3—C2115.94 (14)C13—C12—H12120.4
C4—C3—H3122.0C11—C12—H12120.4
C2—C3—H3122.0C12—C13—C14120.91 (15)
C3—C4—C5123.62 (15)C12—C13—H13119.5
C3—C4—Cl1118.36 (13)C14—C13—H13119.5
C5—C4—Cl1118.01 (12)C15—C14—C13118.81 (15)
C6—C5—C4121.09 (14)C15—C14—C17121.28 (16)
C6—C5—H5119.5C13—C14—C17119.92 (16)
C4—C5—H5119.5C14—C15—C16121.12 (15)
C5—C6—C7114.72 (14)C14—C15—H15119.4
C5—C6—C9123.22 (14)C16—C15—H15119.4
C7—C6—C9122.03 (15)C11—C16—C15119.36 (15)
O1—C7—C6124.46 (14)C11—C16—H16120.3
O1—C7—C2110.50 (13)C15—C16—H16120.3
C6—C7—C2125.05 (15)C14—C17—H17A109.5
C1—C8—O1110.35 (13)C14—C17—H17B109.5
C1—C8—C10134.26 (14)H17A—C17—H17B109.5
O1—C8—C10115.39 (13)C14—C17—H17C109.5
C6—C9—H9A109.5H17A—C17—H17C109.5
C6—C9—H9B109.5H17B—C17—H17C109.5
H9A—C9—H9B109.5
O2—S1—C1—C8−156.13 (14)C1—C2—C7—O10.67 (16)
O3—S1—C1—C8−25.47 (16)C3—C2—C7—C61.2 (2)
C11—S1—C1—C889.91 (15)C1—C2—C7—C6−178.72 (14)
O2—S1—C1—C227.64 (15)C2—C1—C8—O10.08 (17)
O3—S1—C1—C2158.29 (13)S1—C1—C8—O1−176.71 (11)
C11—S1—C1—C2−86.32 (14)C2—C1—C8—C10179.75 (17)
C8—C1—C2—C7−0.45 (17)S1—C1—C8—C103.0 (3)
S1—C1—C2—C7176.38 (11)C7—O1—C8—C10.34 (17)
C8—C1—C2—C3179.68 (17)C7—O1—C8—C10−179.40 (13)
S1—C1—C2—C3−3.5 (3)O2—S1—C11—C16136.28 (13)
C7—C2—C3—C4−1.0 (2)O3—S1—C11—C165.64 (15)
C1—C2—C3—C4178.86 (16)C1—S1—C11—C16−110.88 (14)
C2—C3—C4—C50.5 (2)O2—S1—C11—C12−42.86 (14)
C2—C3—C4—Cl1−178.70 (11)O3—S1—C11—C12−173.49 (13)
C3—C4—C5—C60.0 (2)C1—S1—C11—C1269.99 (14)
Cl1—C4—C5—C6179.14 (12)C16—C11—C12—C13−0.5 (2)
C4—C5—C6—C70.1 (2)S1—C11—C12—C13178.65 (13)
C4—C5—C6—C9−178.22 (15)C11—C12—C13—C14−0.8 (3)
C8—O1—C7—C6178.75 (14)C12—C13—C14—C151.5 (3)
C8—O1—C7—C2−0.64 (16)C12—C13—C14—C17−178.38 (17)
C5—C6—C7—O1180.00 (14)C13—C14—C15—C16−0.8 (3)
C9—C6—C7—O1−1.6 (2)C17—C14—C15—C16179.00 (17)
C5—C6—C7—C2−0.7 (2)C12—C11—C16—C151.1 (3)
C9—C6—C7—C2177.66 (15)S1—C11—C16—C15−178.02 (13)
C3—C2—C7—O1−179.44 (13)C14—C15—C16—C11−0.4 (3)
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.952.523.269 (2)136
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C13—H13⋯O2i 0.952.523.269 (2)136

Symmetry code: (i) .

  8 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 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

4.  A short history of SHELX.

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

5.  Benzofuran derivatives as Abeta-aggregate-specific imaging agents for Alzheimer's disease.

Authors:  Masahiro Ono; Mei-Ping Kung; Catherine Hou; Hank F Kung
Journal:  Nucl Med Biol       Date:  2002-08       Impact factor: 2.408

6.  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

7.  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

8.  5-Chloro-2,7-dimethyl-3-(3-methyl-phenyl-sulfon-yl)-1-benzo-furan.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-04-16
  8 in total
  1 in total

1.  Crystal structure of 5-iodo-2-methyl-3-[(4-methyl-phenyl)-sulfon-yl]-1-benzo-furan.

Authors:  Hong Dae Choi; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-08-20
  1 in total

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