Literature DB >> 21577664

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

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

Abstract

In the title compound, C(16)H(13)BrO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The 4-bromo-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 39.23 (8)°. The crystal structure exhibits weak non-classical inter-molecular C-H⋯O hydrogen bonds and two inter-molecular C-H⋯π inter-actions.

Entities:  

Year:  2009        PMID： 21577664      PMCID： PMC2969963          DOI： 10.1107/S1600536809033509

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


Related literature

For the crystal structures of similar 5-aryl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2006 ▶). 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

C16H13BrO2S M = 349.23 Monoclinic, a = 11.410 (1) Å b = 7.9508 (8) Å c = 15.728 (2) Å β = 99.399 (1)° V = 1407.7 (3) Å3 Z = 4 Mo Kα radiation μ = 3.07 mm−1 T = 173 K 0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.460, T max = 0.579 8551 measured reflections 3195 independent reflections 2551 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.028 wR(F 2) = 0.076 S = 1.04 3195 reflections 183 parameters H-atom parameters constrained Δρmax = 0.52 e Å−3 Δρmin = −0.43 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/S1600536809033509/zl2233sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033509/zl2233Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H13BrO2SF(000) = 704
Mr = 349.23Dx = 1.648 Mg m−3
Monoclinic, P21/cMelting point = 458–459 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.410 (1) ÅCell parameters from 4055 reflections
b = 7.9508 (8) Åθ = 2.4–27.5°
c = 15.728 (2) ŵ = 3.07 mm−1
β = 99.399 (1)°T = 173 K
V = 1407.7 (3) Å3Block, colorless
Z = 40.30 × 0.30 × 0.20 mm
Bruker SMART CCD diffractometer3195 independent reflections
Radiation source: fine-focus sealed tube2551 reflections with I > 2σ(I)
graphiteRint = 0.035
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 1.8°
φ and ω scansh = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)k = −10→10
Tmin = 0.460, Tmax = 0.579l = −13→20
8551 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)] = 0.028Hydrogen site location: difference Fourier map
wR(F2) = 0.076H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0363P)2 + 0.3706P] where P = (Fo2 + 2Fc2)/3
3195 reflections(Δ/σ)max = 0.001
183 parametersΔρmax = 0.52 e Å−3
0 restraintsΔρmin = −0.43 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
Br−0.03613 (2)0.52211 (3)0.242047 (16)0.03659 (10)
S0.73123 (5)0.01241 (6)0.54088 (4)0.02489 (13)
O10.86485 (12)0.41164 (18)0.44262 (10)0.0257 (3)
O20.64757 (15)−0.0857 (2)0.47714 (11)0.0356 (4)
C10.75941 (18)0.2037 (2)0.49091 (13)0.0212 (4)
C20.67604 (18)0.3123 (2)0.43719 (13)0.0210 (4)
C30.55377 (18)0.3170 (2)0.41169 (13)0.0225 (4)
H30.50540.23560.43060.027*
C40.50462 (19)0.4463 (3)0.35708 (14)0.0226 (4)
C50.5801 (2)0.5711 (3)0.33141 (15)0.0264 (5)
H50.54630.65770.29590.032*
C60.7013 (2)0.5696 (3)0.35685 (14)0.0273 (5)
H60.74990.65250.33970.033*
C70.74681 (18)0.4375 (3)0.40949 (14)0.0229 (4)
C80.86971 (18)0.2669 (3)0.49163 (14)0.0238 (4)
C90.37431 (19)0.4570 (2)0.32810 (14)0.0222 (4)
C100.29488 (19)0.4165 (3)0.38373 (13)0.0235 (4)
H100.32420.37740.43880.028*
C110.17330 (19)0.4334 (3)0.35854 (14)0.0256 (5)
H110.12140.40530.39620.031*
C120.1300 (2)0.4926 (3)0.27679 (15)0.0263 (5)
C130.2063 (2)0.5303 (3)0.21940 (15)0.0307 (5)
H130.17630.56790.16410.037*
C140.3277 (2)0.5114 (3)0.24500 (15)0.0283 (5)
H140.37890.53530.20630.034*
C150.98997 (18)0.2164 (3)0.53466 (16)0.0308 (5)
H15A0.98510.11140.56400.046*
H15B1.02150.30120.57560.046*
H15C1.04110.20400.49230.046*
C160.6480 (2)0.0947 (3)0.61869 (15)0.0338 (5)
H16A0.57560.14390.58950.051*
H16B0.69420.17900.65280.051*
H16C0.62960.00540.65540.051*
U11U22U33U12U13U23
Br0.02728 (13)0.04720 (17)0.03369 (15)0.00609 (10)0.00023 (10)−0.00305 (11)
S0.0277 (3)0.0206 (3)0.0263 (3)−0.0030 (2)0.0041 (2)0.0032 (2)
O10.0247 (8)0.0238 (8)0.0286 (8)−0.0054 (6)0.0047 (6)0.0041 (6)
O20.0416 (10)0.0281 (8)0.0358 (9)−0.0115 (7)0.0027 (8)−0.0036 (7)
C10.0264 (10)0.0180 (10)0.0195 (10)−0.0035 (8)0.0044 (8)−0.0012 (8)
C20.0285 (11)0.0174 (9)0.0178 (10)−0.0026 (8)0.0062 (8)−0.0021 (8)
C30.0271 (11)0.0181 (10)0.0231 (11)−0.0043 (8)0.0061 (9)−0.0005 (8)
C40.0267 (11)0.0221 (10)0.0199 (10)−0.0006 (8)0.0060 (9)−0.0022 (8)
C50.0327 (12)0.0228 (10)0.0247 (11)0.0015 (9)0.0079 (9)0.0047 (9)
C60.0327 (12)0.0219 (11)0.0294 (12)−0.0049 (9)0.0112 (10)0.0032 (9)
C70.0254 (11)0.0216 (10)0.0224 (11)−0.0042 (8)0.0059 (9)−0.0034 (9)
C80.0287 (11)0.0207 (10)0.0226 (11)−0.0036 (9)0.0059 (9)−0.0003 (8)
C90.0281 (11)0.0172 (9)0.0215 (11)0.0001 (8)0.0042 (9)−0.0002 (8)
C100.0319 (11)0.0208 (10)0.0178 (10)0.0004 (9)0.0041 (9)0.0023 (8)
C110.0289 (11)0.0265 (11)0.0227 (11)−0.0022 (9)0.0080 (9)−0.0001 (9)
C120.0253 (11)0.0266 (11)0.0264 (12)0.0017 (8)0.0023 (9)−0.0027 (9)
C130.0354 (12)0.0350 (12)0.0210 (11)0.0005 (10)0.0024 (10)0.0047 (10)
C140.0310 (12)0.0336 (12)0.0216 (11)−0.0014 (9)0.0080 (9)0.0035 (9)
C150.0259 (11)0.0283 (12)0.0376 (13)−0.0052 (9)0.0036 (10)0.0024 (10)
C160.0380 (13)0.0381 (13)0.0268 (12)−0.0047 (10)0.0103 (10)0.0019 (10)
Br—C121.900 (2)C8—C151.483 (3)
S—O21.4874 (17)C9—C101.396 (3)
S—C11.766 (2)C9—C141.397 (3)
S—C161.791 (2)C10—C111.386 (3)
O1—C71.378 (3)C10—H100.9300
O1—C81.381 (2)C11—C121.382 (3)
C1—C81.353 (3)C11—H110.9300
C1—C21.450 (3)C12—C131.385 (3)
C2—C31.388 (3)C13—C141.386 (3)
C2—C71.396 (3)C13—H130.9300
C3—C41.397 (3)C14—H140.9300
C3—H30.9300C15—H15A0.9600
C4—C51.415 (3)C15—H15B0.9600
C4—C91.485 (3)C15—H15C0.9600
C5—C61.376 (3)C16—H16A0.9600
C5—H50.9300C16—H16B0.9600
C6—C71.385 (3)C16—H16C0.9600
C6—H60.9300
O2—S—C1107.18 (10)C10—C9—C4120.96 (19)
O2—S—C16107.39 (11)C14—C9—C4120.94 (19)
C1—S—C1698.32 (11)C11—C10—C9121.36 (19)
C7—O1—C8106.44 (15)C11—C10—H10119.3
C8—C1—C2107.74 (17)C9—C10—H10119.3
C8—C1—S123.55 (16)C12—C11—C10119.2 (2)
C2—C1—S128.51 (15)C12—C11—H11120.4
C3—C2—C7119.74 (19)C10—C11—H11120.4
C3—C2—C1135.85 (18)C11—C12—C13120.8 (2)
C7—C2—C1104.40 (17)C11—C12—Br119.84 (17)
C2—C3—C4118.77 (19)C13—C12—Br119.31 (18)
C2—C3—H3120.6C12—C13—C14119.5 (2)
C4—C3—H3120.6C12—C13—H13120.3
C3—C4—C5119.3 (2)C14—C13—H13120.3
C3—C4—C9120.81 (19)C13—C14—C9121.0 (2)
C5—C4—C9119.84 (19)C13—C14—H14119.5
C6—C5—C4122.7 (2)C9—C14—H14119.5
C6—C5—H5118.6C8—C15—H15A109.5
C4—C5—H5118.6C8—C15—H15B109.5
C5—C6—C7116.20 (19)H15A—C15—H15B109.5
C5—C6—H6121.9C8—C15—H15C109.5
C7—C6—H6121.9H15A—C15—H15C109.5
O1—C7—C6125.96 (18)H15B—C15—H15C109.5
O1—C7—C2110.80 (18)S—C16—H16A109.5
C6—C7—C2123.2 (2)S—C16—H16B109.5
C1—C8—O1110.61 (18)H16A—C16—H16B109.5
C1—C8—C15133.9 (2)S—C16—H16C109.5
O1—C8—C15115.47 (17)H16A—C16—H16C109.5
C10—C9—C14118.1 (2)H16B—C16—H16C109.5
O2—S—C1—C8−131.80 (18)C1—C2—C7—C6−179.2 (2)
C16—S—C1—C8117.0 (2)C2—C1—C8—O10.7 (2)
O2—S—C1—C242.4 (2)S—C1—C8—O1175.91 (14)
C16—S—C1—C2−68.8 (2)C2—C1—C8—C15178.9 (2)
C8—C1—C2—C3−179.4 (2)S—C1—C8—C15−5.9 (4)
S—C1—C2—C35.6 (4)C7—O1—C8—C1−0.7 (2)
C8—C1—C2—C7−0.3 (2)C7—O1—C8—C15−179.28 (18)
S—C1—C2—C7−175.27 (16)C3—C4—C9—C1037.8 (3)
C7—C2—C3—C41.3 (3)C5—C4—C9—C10−140.3 (2)
C1—C2—C3—C4−179.7 (2)C3—C4—C9—C14−143.6 (2)
C2—C3—C4—C5−1.8 (3)C5—C4—C9—C1438.3 (3)
C2—C3—C4—C9−179.89 (19)C14—C9—C10—C11−1.6 (3)
C3—C4—C5—C61.1 (3)C4—C9—C10—C11177.03 (19)
C9—C4—C5—C6179.2 (2)C9—C10—C11—C12−0.4 (3)
C4—C5—C6—C70.2 (3)C10—C11—C12—C131.9 (3)
C8—O1—C7—C6179.6 (2)C10—C11—C12—Br−178.41 (16)
C8—O1—C7—C20.5 (2)C11—C12—C13—C14−1.3 (3)
C5—C6—C7—O1−179.8 (2)Br—C12—C13—C14179.01 (16)
C5—C6—C7—C2−0.8 (3)C12—C13—C14—C9−0.8 (3)
C3—C2—C7—O1179.17 (17)C10—C9—C14—C132.2 (3)
C1—C2—C7—O1−0.1 (2)C4—C9—C14—C13−176.4 (2)
C3—C2—C7—C60.1 (3)
D—H···AD—HH···AD···AD—H···A
C10—H10···O2i0.932.663.416 (3)139
C15—H15B···O1ii0.962.663.380 (3)132
C16—H16A···O2i0.962.633.463 (3)145
C13—H13···Cg2iii0.932.863.624 (3)140
C16—H16B···Cg1iv0.962.903.768 (3)152
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C10—H10⋯O2i0.932.663.416 (3)139
C15—H15B⋯O1ii0.962.663.380 (3)132
C16—H16A⋯O2i0.962.633.463 (3)145
C13—H13⋯Cg2iii0.932.863.624 (3)140
C16—H16B⋯Cg1iv0.962.903.768 (3)152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the C9–C14 phenyl ring and the C1/C2/C7/O2/C8 furan ring, respectively.

  4 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.  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
  4 in total
  1 in total

1.  5-(4-Fluoro-phen-yl)-2-methyl-3-methyl-sulfinyl-1-benzofuran.

Authors:  Pil Ja Seo; Hong Dae Choi; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-02
  1 in total

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