Literature DB >> 25309229

Crystal structure of 5-chloro-3-cyclo-hexyl-sulfinyl-2,4,6-trimethyl-1-benzo-furan.

Hong Dae Choi1, Uk Lee2.   

Abstract

In the title compound, C17H21ClO2S, the cyclo-hexyl ring adopts a chair conformation with the C-S bond in an equatorial orientation. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯π hydrogen bonds and a Cl⋯π [3.594 (2) Å] contact into chains along the a-axis direction.

Entities:  

Keywords:  C—H⋯O hydrogen bonds; C—H⋯π inter­actions; benzo­furan; crystal structure; cyclo­hex­yl

Year:  2014        PMID： 25309229      PMCID： PMC4186066          DOI： 10.1107/S1600536814019217

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


Related literature

For the biological activity 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-3-cyclo­hexyl­sulfanyl-2,4,6-trimethyl-1-benzo­furan, see: Choi et al. (1999 ▶). For a related structure, see: Choi et al. (2011 ▶).

Experimental

Crystal data

C17H21ClO2S M = 324.85 Triclinic, a = 5.8612 (1) Å b = 11.6832 (2) Å c = 12.6432 (2) Å α = 65.292 (1)° β = 85.902 (1)° γ = 83.229 (1)° V = 780.79 (2) Å3 Z = 2 Mo Kα radiation μ = 0.38 mm−1 T = 173 K 0.31 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.892, T max = 0.917 13925 measured reflections 3588 independent reflections 3221 reflections with I > 2σ(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.102 S = 1.03 3588 reflections 193 parameters H-atom parameters constrained Δρmax = 0.77 e Å−3 Δρmin = −0.37 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/S1600536814019217/hb7277sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019217/hb7277Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814019217/hb7277Isup3.cml Click here for additional data file. . DOI: 10.1107/S1600536814019217/hb7277fig1.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 . DOI: 10.1107/S1600536814019217/hb7277fig2.tif A view of the C—H⋯O, C—H⋯π and C—Cl⋯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, z; (ii) x + 1, y, z.] CCDC reference: 1021106 Additional supporting information: crystallographic information; 3D view; checkCIF report
C17H21ClO2SZ = 2
Mr = 324.85F(000) = 344
Triclinic, P1Dx = 1.382 Mg m−3
Hall symbol: -P 1Melting point = 417–416 K
a = 5.8612 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.6832 (2) ÅCell parameters from 5736 reflections
c = 12.6432 (2) Åθ = 3.1–27.5°
α = 65.292 (1)°µ = 0.38 mm−1
β = 85.902 (1)°T = 173 K
γ = 83.229 (1)°Block, colourless
V = 780.79 (2) Å30.31 × 0.24 × 0.23 mm
Bruker SMART APEXII CCD diffractometer3588 independent reflections
Radiation source: rotating anode3221 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.024
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.8°
φ and ω scansh = −7→6
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −15→15
Tmin = 0.892, Tmax = 0.917l = −16→16
13925 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)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.102H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0521P)2 + 0.403P] where P = (Fo2 + 2Fc2)/3
3588 reflections(Δ/σ)max = 0.001
193 parametersΔρmax = 0.77 e Å−3
0 restraintsΔρmin = −0.37 e Å−3
Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 7.19 (s, 1H), 2.73 (s, 3H), 2.36 (s, 3H), 2.31 (s, 3H), 1.63-2.12 (m, 5H), 1.10-1.58 (m, 6H).
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
Cl1−0.27225 (7)0.86676 (4)0.02495 (4)0.03675 (13)
S10.57459 (7)0.47693 (4)0.17641 (4)0.02576 (12)
O10.47568 (19)0.69596 (10)0.34877 (10)0.0266 (2)
O20.8052 (2)0.41466 (12)0.22085 (12)0.0382 (3)
C10.4841 (3)0.58674 (14)0.23789 (13)0.0218 (3)
C20.2864 (2)0.68140 (14)0.20410 (13)0.0213 (3)
C30.1136 (3)0.71923 (14)0.12166 (13)0.0225 (3)
C4−0.0488 (3)0.81617 (15)0.12320 (14)0.0257 (3)
C5−0.0466 (3)0.87677 (14)0.19854 (15)0.0282 (3)
C60.1294 (3)0.83926 (15)0.27712 (15)0.0277 (3)
H60.13880.87830.32900.033*
C70.2904 (3)0.74323 (14)0.27712 (13)0.0238 (3)
C80.5900 (3)0.60035 (14)0.32321 (14)0.0243 (3)
C90.1048 (3)0.66135 (16)0.03624 (14)0.0283 (3)
H9A−0.00590.59770.06450.042*
H9B0.25740.62110.02790.042*
H9C0.05720.7275−0.03950.042*
C10−0.2283 (3)0.98104 (17)0.19422 (18)0.0377 (4)
H10A−0.19571.01250.25170.056*
H10B−0.37920.94810.21190.056*
H10C−0.22811.05030.11620.056*
C110.7959 (3)0.53609 (17)0.39374 (15)0.0318 (4)
H11A0.74810.48580.47440.048*
H11B0.89330.59960.39190.048*
H11C0.88260.48030.36160.048*
C120.3682 (3)0.36179 (14)0.25301 (13)0.0220 (3)
H120.21010.40710.24060.026*
C160.2432 (4)0.19538 (17)0.44265 (15)0.0383 (4)
H16A0.27760.15070.52650.046*
H16B0.08370.23610.43570.046*
C170.4088 (3)0.29673 (16)0.38293 (14)0.0318 (4)
H17A0.38610.36010.41660.038*
H17B0.56910.25730.39660.038*
C130.3866 (3)0.26742 (15)0.19771 (14)0.0274 (3)
H13A0.35000.31250.11420.033*
H13B0.54590.22670.20360.033*
C140.2215 (3)0.16667 (16)0.25851 (15)0.0325 (4)
H14A0.06140.20660.24580.039*
H14B0.24150.10370.22430.039*
C150.2635 (4)0.10016 (16)0.38823 (16)0.0382 (4)
H15A0.41900.05390.40130.046*
H15B0.15000.03780.42600.046*
U11U22U33U12U13U23
Cl10.0255 (2)0.0385 (2)0.0353 (2)0.00422 (17)−0.00709 (17)−0.00539 (18)
S10.0211 (2)0.0256 (2)0.0315 (2)−0.00217 (14)0.00493 (15)−0.01365 (16)
O10.0263 (6)0.0269 (6)0.0297 (6)−0.0042 (4)−0.0037 (5)−0.0137 (5)
O20.0201 (6)0.0393 (7)0.0566 (8)0.0026 (5)0.0011 (5)−0.0231 (6)
C10.0180 (7)0.0213 (7)0.0255 (7)−0.0026 (5)0.0000 (5)−0.0088 (6)
C20.0181 (7)0.0201 (7)0.0245 (7)−0.0038 (5)0.0022 (6)−0.0078 (6)
C30.0203 (7)0.0218 (7)0.0225 (7)−0.0044 (6)0.0019 (6)−0.0060 (6)
C40.0195 (7)0.0243 (7)0.0259 (8)−0.0019 (6)−0.0001 (6)−0.0033 (6)
C50.0256 (8)0.0198 (7)0.0330 (8)−0.0020 (6)0.0059 (6)−0.0057 (6)
C60.0308 (8)0.0225 (7)0.0319 (8)−0.0057 (6)0.0049 (7)−0.0133 (6)
C70.0227 (7)0.0226 (7)0.0258 (7)−0.0049 (6)0.0002 (6)−0.0092 (6)
C80.0209 (7)0.0231 (7)0.0283 (8)−0.0044 (6)0.0001 (6)−0.0096 (6)
C90.0266 (8)0.0322 (8)0.0259 (8)−0.0018 (6)−0.0032 (6)−0.0116 (7)
C100.0320 (9)0.0264 (8)0.0490 (11)0.0030 (7)0.0068 (8)−0.0128 (8)
C110.0247 (8)0.0352 (9)0.0323 (9)−0.0022 (7)−0.0074 (7)−0.0100 (7)
C120.0192 (7)0.0222 (7)0.0247 (7)−0.0009 (5)0.0002 (5)−0.0102 (6)
C160.0529 (12)0.0331 (9)0.0266 (9)−0.0095 (8)0.0087 (8)−0.0101 (7)
C170.0410 (10)0.0318 (9)0.0244 (8)−0.0058 (7)−0.0009 (7)−0.0128 (7)
C130.0326 (9)0.0262 (8)0.0256 (8)−0.0027 (6)0.0008 (6)−0.0130 (6)
C140.0376 (9)0.0267 (8)0.0358 (9)−0.0067 (7)0.0010 (7)−0.0150 (7)
C150.0514 (12)0.0244 (8)0.0347 (9)−0.0078 (8)0.0070 (8)−0.0084 (7)
Cl1—C41.7444 (16)C10—H10B0.9800
S1—O21.4857 (12)C10—H10C0.9800
S1—C11.7737 (16)C11—H11A0.9800
S1—C121.8268 (16)C11—H11B0.9800
O1—C71.3734 (19)C11—H11C0.9800
O1—C81.3768 (19)C12—C171.517 (2)
C1—C81.355 (2)C12—C131.524 (2)
C1—C21.456 (2)C12—H121.0000
C2—C71.392 (2)C16—C151.524 (3)
C2—C31.403 (2)C16—C171.527 (3)
C3—C41.397 (2)C16—H16A0.9900
C3—C91.501 (2)C16—H16B0.9900
C4—C51.406 (2)C17—H17A0.9900
C5—C61.385 (2)C17—H17B0.9900
C5—C101.506 (2)C13—C141.523 (2)
C6—C71.378 (2)C13—H13A0.9900
C6—H60.9500C13—H13B0.9900
C8—C111.482 (2)C14—C151.517 (2)
C9—H9A0.9800C14—H14A0.9900
C9—H9B0.9800C14—H14B0.9900
C9—H9C0.9800C15—H15A0.9900
C10—H10A0.9800C15—H15B0.9900
O2—S1—C1108.70 (7)C8—C11—H11B109.5
O2—S1—C12106.89 (7)H11A—C11—H11B109.5
C1—S1—C1298.02 (7)C8—C11—H11C109.5
C7—O1—C8106.43 (12)H11A—C11—H11C109.5
C8—C1—C2107.18 (13)H11B—C11—H11C109.5
C8—C1—S1126.24 (12)C17—C12—C13111.82 (13)
C2—C1—S1126.56 (12)C17—C12—S1112.03 (11)
C7—C2—C3119.57 (14)C13—C12—S1107.37 (10)
C7—C2—C1104.35 (13)C17—C12—H12108.5
C3—C2—C1136.08 (14)C13—C12—H12108.5
C4—C3—C2115.37 (14)S1—C12—H12108.5
C4—C3—C9122.03 (14)C15—C16—C17111.07 (15)
C2—C3—C9122.59 (14)C15—C16—H16A109.4
C3—C4—C5124.84 (15)C17—C16—H16A109.4
C3—C4—Cl1118.17 (13)C15—C16—H16B109.4
C5—C4—Cl1116.99 (12)C17—C16—H16B109.4
C6—C5—C4118.38 (14)H16A—C16—H16B108.0
C6—C5—C10120.13 (16)C12—C17—C16110.44 (14)
C4—C5—C10121.48 (16)C12—C17—H17A109.6
C7—C6—C5117.47 (15)C16—C17—H17A109.6
C7—C6—H6121.3C12—C17—H17B109.6
C5—C6—H6121.3C16—C17—H17B109.6
O1—C7—C6124.62 (15)H17A—C17—H17B108.1
O1—C7—C2111.05 (13)C14—C13—C12110.48 (13)
C6—C7—C2124.33 (15)C14—C13—H13A109.6
C1—C8—O1110.96 (13)C12—C13—H13A109.6
C1—C8—C11134.70 (15)C14—C13—H13B109.6
O1—C8—C11114.33 (14)C12—C13—H13B109.6
C3—C9—H9A109.5H13A—C13—H13B108.1
C3—C9—H9B109.5C15—C14—C13111.19 (15)
H9A—C9—H9B109.5C15—C14—H14A109.4
C3—C9—H9C109.5C13—C14—H14A109.4
H9A—C9—H9C109.5C15—C14—H14B109.4
H9B—C9—H9C109.5C13—C14—H14B109.4
C5—C10—H10A109.5H14A—C14—H14B108.0
C5—C10—H10B109.5C14—C15—C16110.65 (14)
H10A—C10—H10B109.5C14—C15—H15A109.5
C5—C10—H10C109.5C16—C15—H15A109.5
H10A—C10—H10C109.5C14—C15—H15B109.5
H10B—C10—H10C109.5C16—C15—H15B109.5
C8—C11—H11A109.5H15A—C15—H15B108.1
O2—S1—C1—C8−8.41 (17)C5—C6—C7—O1179.49 (14)
C12—S1—C1—C8102.54 (15)C5—C6—C7—C2−0.4 (2)
O2—S1—C1—C2169.73 (13)C3—C2—C7—O1−177.97 (13)
C12—S1—C1—C2−79.33 (14)C1—C2—C7—O11.59 (17)
C8—C1—C2—C7−1.28 (17)C3—C2—C7—C62.0 (2)
S1—C1—C2—C7−179.71 (11)C1—C2—C7—C6−178.49 (15)
C8—C1—C2—C3178.16 (17)C2—C1—C8—O10.56 (17)
S1—C1—C2—C3−0.3 (3)S1—C1—C8—O1178.99 (11)
C7—C2—C3—C4−2.1 (2)C2—C1—C8—C11−179.83 (17)
C1—C2—C3—C4178.50 (16)S1—C1—C8—C11−1.4 (3)
C7—C2—C3—C9176.98 (14)C7—O1—C8—C10.42 (17)
C1—C2—C3—C9−2.4 (3)C7—O1—C8—C11−179.28 (13)
C2—C3—C4—C51.0 (2)O2—S1—C12—C1745.90 (13)
C9—C3—C4—C5−178.09 (15)C1—S1—C12—C17−66.51 (12)
C2—C3—C4—Cl1−178.93 (11)O2—S1—C12—C13−77.25 (12)
C9—C3—C4—Cl12.0 (2)C1—S1—C12—C13170.35 (11)
C3—C4—C5—C60.4 (2)C13—C12—C17—C16−55.75 (19)
Cl1—C4—C5—C6−179.62 (12)S1—C12—C17—C16−176.35 (12)
C3—C4—C5—C10179.79 (15)C15—C16—C17—C1256.0 (2)
Cl1—C4—C5—C10−0.3 (2)C17—C12—C13—C1455.82 (18)
C4—C5—C6—C7−0.7 (2)S1—C12—C13—C14179.10 (11)
C10—C5—C6—C7179.89 (15)C12—C13—C14—C15−56.10 (19)
C8—O1—C7—C6178.78 (15)C13—C14—C15—C1656.9 (2)
C8—O1—C7—C2−1.29 (17)C17—C16—C15—C14−56.7 (2)
D—H···AD—HH···AD···AD—H···A
C9—H9A···O2i0.982.533.438 (2)154
C12—H12···O2i1.002.393.3072 (19)152
C11—H11b···Cg2i0.982.833.533 (2)129
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 benzene ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C9—H9A⋯O2i 0.982.533.438 (2)154
C12—H12⋯O2i 1.002.393.3072 (19)152
C11—H11b⋯Cg2i 0.982.833.533 (2)129

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

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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
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4.  A short history of SHELX.

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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-3-cyclo-hexyl-sulfinyl-2-methyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-03-09
  8 in total

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