Literature DB >> 22090997

2-(5-Cyclo-hexyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetic acid.

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

Abstract

In the title compound, C(17)H(20)O(3)S, the cyclo-hexyl ring adopts a chair conformation. In the crystal, the carboxyl groups are involved in inter-molecular O-H⋯O hydrogen bonds, which link the mol-ecules into centrosymmetric dimers. These dimers are further stabilized by weak inter-molecular C-H⋯O hydrogen bonds. In addition, the crystal structure also exhibits aromatic π-π inter-actions between the furan rings of adjacent mol-ecules [centroid-centroid distance = 3.505 (2) Å, inter-planar distance = 3.385 (2) Å and slippage = 0.909 (2) Å], and inter-molecular C-H⋯π inter-actions.

Entities:  

Year:  2011        PMID： 22090997      PMCID： PMC3212340          DOI： 10.1107/S1600536811026298

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 related 2-(5-alkyl-3-methyl­sulfanyl-1-benzofuran-2-yl) acetic acid derivatives, see: Choi et al. (2009 ▶); Seo et al. (2007 ▶).

Experimental

Crystal data

C17H20O3S M = 304.40 Triclinic, a = 7.3434 (2) Å b = 9.0765 (3) Å c = 11.6009 (4) Å α = 86.086 (2)° β = 86.083 (2)° γ = 86.690 (2)° V = 768.53 (4) Å3 Z = 2 Mo Kα radiation μ = 0.22 mm−1 T = 173 K 0.32 × 0.21 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.934, T max = 0.978 14240 measured reflections 3864 independent reflections 3255 reflections with I > 2σ(I) R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.100 S = 1.05 3864 reflections 191 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.26 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) global, I. DOI: 10.1107/S1600536811026298/rk2282sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026298/rk2282Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811026298/rk2282Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H20O3SZ = 2
Mr = 304.40F(000) = 324
Triclinic, P1Dx = 1.315 Mg m−3
Hall symbol: -P 1Melting point = 423–424 K
a = 7.3434 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.0765 (3) ÅCell parameters from 6244 reflections
c = 11.6009 (4) Åθ = 2.3–28.4°
α = 86.086 (2)°µ = 0.22 mm−1
β = 86.083 (2)°T = 173 K
γ = 86.690 (2)°Block, colourless
V = 768.53 (4) Å30.32 × 0.21 × 0.10 mm
Bruker SMART APEXII CCD diffractometer3864 independent reflections
Radiation source: rotating anode3255 reflections with I > 2σ(I)
graphite multilayerRint = 0.030
Detector resolution: 10.0 pixels mm-1θmax = 28.6°, θmin = 1.8°
φ and ω scansh = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −9→12
Tmin = 0.934, Tmax = 0.978l = −15→15
14240 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)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.100H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0444P)2 + 0.2671P] where P = (Fo2 + 2Fc2)/3
3864 reflections(Δ/σ)max = 0.001
191 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
S10.39556 (5)0.81571 (4)0.07230 (3)0.02882 (11)
O10.75966 (12)0.47823 (10)0.08350 (8)0.0242 (2)
O20.88107 (14)0.86762 (12)0.06964 (8)0.0308 (2)
O30.96423 (14)0.89156 (11)−0.11894 (8)0.0304 (2)
H3O1.01200.9672−0.09950.046*
C10.52945 (18)0.65343 (14)0.09979 (11)0.0211 (3)
C20.49420 (17)0.53545 (14)0.18707 (11)0.0201 (3)
C30.35767 (17)0.50941 (14)0.27432 (11)0.0209 (3)
H30.25770.57940.28520.025*
C40.36936 (18)0.37992 (14)0.34536 (11)0.0218 (3)
C50.51779 (19)0.27762 (15)0.32655 (12)0.0267 (3)
H50.52430.18890.37490.032*
C60.65490 (19)0.30100 (15)0.24036 (12)0.0271 (3)
H60.75440.23090.22830.032*
C70.63899 (18)0.43164 (14)0.17300 (11)0.0220 (3)
C80.68847 (18)0.61388 (14)0.04136 (11)0.0222 (3)
C90.22459 (18)0.35080 (15)0.44187 (11)0.0226 (3)
H90.14080.44160.44410.027*
C100.1076 (2)0.22267 (17)0.42058 (13)0.0308 (3)
H10A0.18600.13050.41670.037*
H10B0.05190.24230.34530.037*
C11−0.0433 (2)0.20246 (17)0.51702 (13)0.0329 (3)
H11A−0.12950.29050.51520.039*
H11B−0.11230.11540.50350.039*
C120.0348 (2)0.18098 (17)0.63539 (13)0.0339 (3)
H12A−0.06660.17570.69600.041*
H12B0.10850.08620.64060.041*
C130.1536 (2)0.30655 (19)0.65673 (13)0.0330 (3)
H13A0.20990.28540.73160.040*
H13B0.07650.39930.66170.040*
C140.3035 (2)0.32710 (19)0.56051 (12)0.0331 (3)
H14A0.38890.23860.56140.040*
H14B0.37340.41350.57460.040*
C150.79618 (19)0.68726 (15)−0.05668 (12)0.0250 (3)
H15A0.71470.7137−0.12030.030*
H15B0.89270.6157−0.08550.030*
C160.88468 (17)0.82431 (14)−0.02779 (11)0.0221 (3)
C170.4488 (2)0.91892 (17)0.19209 (14)0.0352 (3)
H17A0.42420.86000.26490.053*
H17B0.37291.01130.19240.053*
H17C0.57810.94140.18400.053*
U11U22U33U12U13U23
S10.0332 (2)0.02291 (18)0.0301 (2)0.00036 (13)−0.00535 (14)0.00250 (13)
O10.0233 (5)0.0225 (5)0.0260 (5)−0.0032 (4)0.0036 (4)0.0003 (4)
O20.0374 (6)0.0353 (6)0.0211 (5)−0.0181 (4)0.0030 (4)−0.0037 (4)
O30.0382 (6)0.0302 (5)0.0235 (5)−0.0169 (4)0.0045 (4)−0.0020 (4)
C10.0225 (6)0.0191 (6)0.0223 (6)−0.0060 (5)−0.0021 (5)−0.0004 (5)
C20.0222 (6)0.0191 (6)0.0197 (6)−0.0061 (5)−0.0025 (5)−0.0013 (5)
C30.0204 (6)0.0210 (6)0.0215 (6)−0.0034 (5)−0.0011 (5)−0.0021 (5)
C40.0236 (6)0.0223 (6)0.0201 (6)−0.0067 (5)−0.0013 (5)−0.0012 (5)
C50.0305 (7)0.0226 (6)0.0262 (7)−0.0026 (5)−0.0007 (6)0.0036 (5)
C60.0264 (7)0.0233 (7)0.0304 (7)0.0017 (5)0.0007 (6)0.0006 (6)
C70.0216 (6)0.0230 (6)0.0215 (6)−0.0057 (5)0.0008 (5)−0.0011 (5)
C80.0257 (6)0.0200 (6)0.0215 (6)−0.0069 (5)−0.0019 (5)−0.0012 (5)
C90.0237 (6)0.0233 (6)0.0208 (6)−0.0061 (5)0.0000 (5)0.0008 (5)
C100.0330 (8)0.0339 (8)0.0270 (7)−0.0150 (6)0.0009 (6)−0.0044 (6)
C110.0315 (8)0.0336 (8)0.0346 (8)−0.0160 (6)0.0034 (6)−0.0037 (6)
C120.0361 (8)0.0329 (8)0.0310 (8)−0.0076 (6)0.0071 (6)0.0055 (6)
C130.0322 (8)0.0452 (9)0.0217 (7)−0.0085 (6)−0.0013 (6)0.0012 (6)
C140.0285 (7)0.0485 (9)0.0233 (7)−0.0132 (6)−0.0018 (6)0.0002 (6)
C150.0288 (7)0.0239 (6)0.0227 (7)−0.0088 (5)0.0024 (5)−0.0023 (5)
C160.0196 (6)0.0233 (6)0.0233 (6)−0.0038 (5)0.0000 (5)0.0008 (5)
C170.0402 (9)0.0269 (7)0.0388 (9)0.0018 (6)−0.0023 (7)−0.0063 (6)
S1—C11.7463 (13)C9—H91.0000
S1—C171.8044 (16)C10—C111.530 (2)
O1—C71.3783 (15)C10—H10A0.9900
O1—C81.3808 (16)C10—H10B0.9900
O2—C161.2200 (16)C11—C121.520 (2)
O3—C161.3041 (16)C11—H11A0.9900
O3—H3O0.8400C11—H11B0.9900
C1—C81.3523 (19)C12—C131.518 (2)
C1—C21.4446 (17)C12—H12A0.9900
C2—C71.3880 (18)C12—H12B0.9900
C2—C31.3934 (17)C13—C141.523 (2)
C3—C41.3906 (18)C13—H13A0.9900
C3—H30.9500C13—H13B0.9900
C4—C51.4058 (19)C14—H14A0.9900
C4—C91.5109 (18)C14—H14B0.9900
C5—C61.3844 (19)C15—C161.5040 (18)
C5—H50.9500C15—H15A0.9900
C6—C71.3786 (19)C15—H15B0.9900
C6—H60.9500C17—H17A0.9800
C8—C151.4823 (18)C17—H17B0.9800
C9—C141.5268 (19)C17—H17C0.9800
C9—C101.5280 (19)
C1—S1—C17100.05 (7)C12—C11—C10111.44 (12)
C7—O1—C8105.90 (10)C12—C11—H11A109.3
C16—O3—H3O109.5C10—C11—H11A109.3
C8—C1—C2106.46 (11)C12—C11—H11B109.3
C8—C1—S1125.80 (10)C10—C11—H11B109.3
C2—C1—S1127.74 (10)H11A—C11—H11B108.0
C7—C2—C3119.29 (12)C13—C12—C11111.38 (12)
C7—C2—C1105.62 (11)C13—C12—H12A109.4
C3—C2—C1135.08 (12)C11—C12—H12A109.4
C4—C3—C2119.28 (12)C13—C12—H12B109.4
C4—C3—H3120.4C11—C12—H12B109.4
C2—C3—H3120.4H12A—C12—H12B108.0
C3—C4—C5119.13 (12)C12—C13—C14111.49 (13)
C3—C4—C9120.14 (12)C12—C13—H13A109.3
C5—C4—C9120.73 (12)C14—C13—H13A109.3
C6—C5—C4122.61 (13)C12—C13—H13B109.3
C6—C5—H5118.7C14—C13—H13B109.3
C4—C5—H5118.7H13A—C13—H13B108.0
C7—C6—C5116.27 (13)C13—C14—C9111.51 (12)
C7—C6—H6121.9C13—C14—H14A109.3
C5—C6—H6121.9C9—C14—H14A109.3
O1—C7—C6126.17 (12)C13—C14—H14B109.3
O1—C7—C2110.43 (11)C9—C14—H14B109.3
C6—C7—C2123.40 (12)H14A—C14—H14B108.0
C1—C8—O1111.59 (11)C8—C15—C16114.63 (11)
C1—C8—C15132.48 (13)C8—C15—H15A108.6
O1—C8—C15115.93 (11)C16—C15—H15A108.6
C4—C9—C14112.67 (11)C8—C15—H15B108.6
C4—C9—C10112.85 (11)C16—C15—H15B108.6
C14—C9—C10110.37 (12)H15A—C15—H15B107.6
C4—C9—H9106.8O2—C16—O3124.13 (12)
C14—C9—H9106.8O2—C16—C15123.70 (12)
C10—C9—H9106.8O3—C16—C15112.17 (11)
C9—C10—C11111.07 (12)S1—C17—H17A109.5
C9—C10—H10A109.4S1—C17—H17B109.5
C11—C10—H10A109.4H17A—C17—H17B109.5
C9—C10—H10B109.4S1—C17—H17C109.5
C11—C10—H10B109.4H17A—C17—H17C109.5
H10A—C10—H10B108.0H17B—C17—H17C109.5
C17—S1—C1—C8−104.94 (13)S1—C1—C8—O1−179.32 (9)
C17—S1—C1—C275.49 (13)C2—C1—C8—C15−179.89 (13)
C8—C1—C2—C7−0.22 (14)S1—C1—C8—C150.5 (2)
S1—C1—C2—C7179.42 (10)C7—O1—C8—C1−0.29 (14)
C8—C1—C2—C3179.08 (14)C7—O1—C8—C15179.88 (11)
S1—C1—C2—C3−1.3 (2)C3—C4—C9—C14−122.24 (14)
C7—C2—C3—C4−0.06 (18)C5—C4—C9—C1457.33 (17)
C1—C2—C3—C4−179.28 (13)C3—C4—C9—C10111.93 (14)
C2—C3—C4—C5−0.68 (19)C5—C4—C9—C10−68.49 (16)
C2—C3—C4—C9178.90 (11)C4—C9—C10—C11−176.96 (12)
C3—C4—C5—C60.6 (2)C14—C9—C10—C1155.98 (16)
C9—C4—C5—C6−178.95 (13)C9—C10—C11—C12−55.76 (17)
C4—C5—C6—C70.2 (2)C10—C11—C12—C1354.84 (17)
C8—O1—C7—C6179.81 (13)C11—C12—C13—C14−54.64 (18)
C8—O1—C7—C20.14 (14)C12—C13—C14—C955.54 (18)
C5—C6—C7—O1179.39 (12)C4—C9—C14—C13176.83 (12)
C5—C6—C7—C2−1.0 (2)C10—C9—C14—C13−56.01 (17)
C3—C2—C7—O1−179.39 (11)C1—C8—C15—C1669.12 (19)
C1—C2—C7—O10.04 (14)O1—C8—C15—C16−111.10 (13)
C3—C2—C7—C60.9 (2)C8—C15—C16—O25.1 (2)
C1—C2—C7—C6−179.63 (13)C8—C15—C16—O3−174.44 (12)
C2—C1—C8—O10.32 (15)
Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and C2–C7 benzene ring, respectively.
D—H···AD—HH···AD···AD—H···A
C6—H6···O3i0.952.593.4777 (17)157
O3—H3O···O2ii0.841.802.6347 (15)176
C13—H13A···Cg1iii0.992.823.581 (2)134
C14—H14B···Cg2iii0.992.853.678 (2)147
C15—H15A···Cg2iv0.992.673.501 (2)142
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and C2–C7 benzene ring, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C6—H6⋯O3i0.952.593.4777 (17)157
O3—H3O⋯O2ii0.841.802.6347 (15)176
C13—H13A⋯Cg1iii0.992.823.581 (2)134
C14—H14B⋯Cg2iii0.992.853.678 (2)147
C15—H15A⋯Cg2iv0.992.673.501 (2)142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

  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.  2-(5-Isopropyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetic acid.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-10

6.  2-(3-Methyl-sulfanyl-5-propyl-1-benzofuran-2-yl)acetic acid.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-04-08

7.  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

8.  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 in total
  1 in total

1.  2-(5-Cyclo-hexyl-3-isopropyl-sulfanyl-1-benzofuran-2-yl)acetic acid.

Authors:  Hong Dae Choi; Pil Ja Seo; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-01-14
  1 in total

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