Literature DB >> 23284540

5-Bromo-3-(4-fluoro-phenyl-sulfin-yl)-2-phenyl-1-benzofuran.

Hong Dae Choi1, Pil Ja Seo, Uk Lee.   

Abstract

In the title compound, C(20)H(12)BrFO(2)S, the dihedral angles between the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment and the pendant 4-fluoro-phenyl and phenyl rings are 84.98 (5) and 40.98 (6)°, respectively. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯π inter-actions.

Entities:  

Year:  2012        PMID： 23284540      PMCID： PMC3515320          DOI： 10.1107/S1600536812044054

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


Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C20H12BrFO2S M = 415.27 Triclinic, a = 9.2288 (2) Å b = 9.4790 (2) Å c = 10.4939 (2) Å α = 67.396 (1)° β = 89.933 (1)° γ = 82.373 (1)° V = 838.74 (3) Å3 Z = 2 Mo Kα radiation μ = 2.60 mm−1 T = 173 K 0.39 × 0.33 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.557, T max = 0.746 15136 measured reflections 3888 independent reflections 3417 reflections with I > 2σ(I) R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.079 S = 1.05 3888 reflections 226 parameters H-atom parameters constrained Δρmax = 0.65 e Å−3 Δρmin = −0.74 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. Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044054/bv2213sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044054/bv2213Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812044054/bv2213Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H12BrFO2SZ = 2
Mr = 415.27F(000) = 416
Triclinic, P1Dx = 1.644 Mg m−3
Hall symbol: -P 1Melting point = 446–445 K
a = 9.2288 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.4790 (2) ÅCell parameters from 6293 reflections
c = 10.4939 (2) Åθ = 2.2–27.5°
α = 67.396 (1)°µ = 2.60 mm−1
β = 89.933 (1)°T = 173 K
γ = 82.373 (1)°Block, colourless
V = 838.74 (3) Å30.39 × 0.33 × 0.22 mm
Bruker SMART APEXII CCD diffractometer3888 independent reflections
Radiation source: rotating anode3417 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.045
Detector resolution: 10.0 pixels mm-1θmax = 27.6°, θmin = 2.1°
φ and ω scansh = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −12→12
Tmin = 0.557, Tmax = 0.746l = −13→13
15136 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)] = 0.030Hydrogen site location: difference Fourier map
wR(F2) = 0.079H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.032P)2 + 0.4488P] where P = (Fo2 + 2Fc2)/3
3888 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.65 e Å−3
0 restraintsΔρmin = −0.74 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
Br10.44656 (2)1.17299 (2)0.60200 (2)0.03743 (9)
S10.34716 (5)0.48730 (6)0.74923 (5)0.02461 (11)
F1−0.06628 (17)0.76294 (19)0.26600 (15)0.0505 (4)
O10.25847 (16)0.62748 (16)1.05071 (14)0.0266 (3)
O20.49317 (16)0.5237 (2)0.69525 (17)0.0363 (4)
C10.2987 (2)0.5932 (2)0.8526 (2)0.0234 (4)
C20.3270 (2)0.7466 (2)0.8310 (2)0.0241 (4)
C30.3706 (2)0.8705 (2)0.7217 (2)0.0267 (4)
H30.38880.86560.63430.032*
C40.3862 (2)1.0009 (2)0.7466 (2)0.0282 (4)
C50.3610 (2)1.0122 (3)0.8731 (2)0.0321 (5)
H50.37311.10460.88480.039*
C60.3183 (2)0.8897 (3)0.9821 (2)0.0314 (5)
H60.30120.89461.06970.038*
C70.3020 (2)0.7600 (2)0.9568 (2)0.0255 (4)
C80.2584 (2)0.5276 (2)0.9848 (2)0.0240 (4)
C90.2165 (2)0.3774 (2)1.0659 (2)0.0247 (4)
C100.2675 (2)0.2991 (2)1.2042 (2)0.0288 (4)
H100.32740.34521.24610.035*
C110.2304 (3)0.1551 (3)1.2792 (2)0.0367 (5)
H110.26720.10071.37230.044*
C120.1402 (3)0.0891 (3)1.2200 (3)0.0421 (6)
H120.1140−0.00971.27290.051*
C130.0878 (3)0.1664 (3)1.0836 (3)0.0403 (5)
H130.02560.12091.04320.048*
C140.1259 (2)0.3097 (3)1.0066 (2)0.0330 (5)
H140.09050.36240.91290.040*
C150.2184 (2)0.5861 (2)0.60419 (19)0.0227 (4)
C160.0772 (2)0.6487 (3)0.6157 (2)0.0299 (4)
H160.04680.65020.70170.036*
C17−0.0195 (2)0.7090 (3)0.5006 (2)0.0351 (5)
H17−0.11680.75310.50600.042*
C180.0288 (2)0.7034 (3)0.3788 (2)0.0328 (5)
C190.1680 (3)0.6428 (3)0.3644 (2)0.0320 (5)
H190.19770.64200.27790.038*
C200.2640 (2)0.5827 (2)0.4797 (2)0.0267 (4)
H200.36120.53910.47350.032*
U11U22U33U12U13U23
Br10.04254 (14)0.02593 (13)0.04180 (14)−0.00937 (9)0.01229 (10)−0.00950 (10)
S10.0270 (2)0.0261 (3)0.0238 (2)−0.00184 (18)0.00172 (18)−0.0136 (2)
F10.0572 (9)0.0564 (10)0.0337 (7)0.0041 (7)−0.0179 (7)−0.0169 (7)
O10.0355 (8)0.0270 (7)0.0204 (7)−0.0083 (6)0.0049 (5)−0.0113 (6)
O20.0255 (7)0.0541 (10)0.0394 (9)−0.0050 (7)0.0052 (6)−0.0293 (8)
C10.0251 (9)0.0254 (10)0.0215 (9)−0.0040 (7)0.0017 (7)−0.0112 (8)
C20.0239 (9)0.0264 (10)0.0241 (9)−0.0031 (7)0.0015 (7)−0.0123 (8)
C30.0288 (10)0.0271 (10)0.0246 (10)−0.0045 (8)0.0052 (8)−0.0104 (8)
C40.0258 (10)0.0253 (10)0.0318 (10)−0.0049 (8)0.0037 (8)−0.0090 (9)
C50.0362 (11)0.0275 (11)0.0369 (12)−0.0054 (9)0.0012 (9)−0.0170 (10)
C60.0402 (12)0.0327 (12)0.0274 (10)−0.0070 (9)0.0035 (9)−0.0176 (9)
C70.0279 (10)0.0267 (10)0.0231 (9)−0.0060 (8)0.0034 (7)−0.0103 (8)
C80.0243 (9)0.0276 (10)0.0231 (9)−0.0043 (7)−0.0002 (7)−0.0130 (8)
C90.0247 (9)0.0258 (10)0.0250 (9)−0.0042 (7)0.0047 (7)−0.0112 (8)
C100.0281 (10)0.0293 (11)0.0279 (10)−0.0018 (8)0.0026 (8)−0.0107 (9)
C110.0433 (12)0.0293 (12)0.0298 (11)−0.0002 (9)0.0084 (9)−0.0048 (9)
C120.0493 (14)0.0257 (12)0.0510 (15)−0.0111 (10)0.0186 (11)−0.0126 (11)
C130.0401 (13)0.0371 (13)0.0515 (15)−0.0134 (10)0.0071 (11)−0.0233 (12)
C140.0324 (11)0.0363 (12)0.0341 (11)−0.0072 (9)0.0014 (9)−0.0170 (10)
C150.0267 (9)0.0223 (9)0.0208 (9)−0.0064 (7)0.0022 (7)−0.0093 (8)
C160.0285 (10)0.0374 (12)0.0265 (10)−0.0041 (8)0.0047 (8)−0.0155 (9)
C170.0296 (11)0.0419 (13)0.0331 (11)−0.0004 (9)−0.0009 (9)−0.0154 (10)
C180.0405 (12)0.0299 (11)0.0263 (10)−0.0058 (9)−0.0070 (9)−0.0087 (9)
C190.0452 (12)0.0314 (11)0.0215 (10)−0.0089 (9)0.0060 (9)−0.0116 (9)
C200.0298 (10)0.0261 (10)0.0262 (10)−0.0059 (8)0.0072 (8)−0.0118 (9)
Br1—C41.900 (2)C9—C101.400 (3)
S1—O21.4923 (16)C10—C111.378 (3)
S1—C11.7609 (19)C10—H100.9500
S1—C151.7941 (19)C11—C121.382 (4)
F1—C181.359 (2)C11—H110.9500
O1—C81.371 (2)C12—C131.385 (4)
O1—C71.375 (2)C12—H120.9500
C1—C81.358 (3)C13—C141.380 (3)
C1—C21.443 (3)C13—H130.9500
C2—C71.390 (3)C14—H140.9500
C2—C31.394 (3)C15—C201.383 (3)
C3—C41.382 (3)C15—C161.383 (3)
C3—H30.9500C16—C171.385 (3)
C4—C51.389 (3)C16—H160.9500
C5—C61.382 (3)C17—C181.371 (3)
C5—H50.9500C17—H170.9500
C6—C71.380 (3)C18—C191.369 (3)
C6—H60.9500C19—C201.383 (3)
C8—C91.454 (3)C19—H190.9500
C9—C141.396 (3)C20—H200.9500
O2—S1—C1107.36 (9)C11—C10—H10120.1
O2—S1—C15105.38 (9)C9—C10—H10120.1
C1—S1—C15100.79 (9)C10—C11—C12120.5 (2)
C8—O1—C7106.44 (15)C10—C11—H11119.8
C8—C1—C2107.19 (17)C12—C11—H11119.8
C8—C1—S1123.20 (15)C11—C12—C13120.2 (2)
C2—C1—S1127.98 (15)C11—C12—H12119.9
C7—C2—C3119.21 (18)C13—C12—H12119.9
C7—C2—C1104.74 (18)C14—C13—C12120.0 (2)
C3—C2—C1136.05 (18)C14—C13—H13120.0
C4—C3—C2116.90 (19)C12—C13—H13120.0
C4—C3—H3121.6C13—C14—C9120.2 (2)
C2—C3—H3121.6C13—C14—H14119.9
C3—C4—C5123.2 (2)C9—C14—H14119.9
C3—C4—Br1118.81 (16)C20—C15—C16120.94 (18)
C5—C4—Br1118.02 (16)C20—C15—S1115.41 (15)
C6—C5—C4120.30 (19)C16—C15—S1123.34 (15)
C6—C5—H5119.8C15—C16—C17119.43 (19)
C4—C5—H5119.8C15—C16—H16120.3
C7—C6—C5116.44 (19)C17—C16—H16120.3
C7—C6—H6121.8C18—C17—C16118.3 (2)
C5—C6—H6121.8C18—C17—H17120.9
O1—C7—C6125.29 (18)C16—C17—H17120.9
O1—C7—C2110.73 (17)F1—C18—C19118.31 (19)
C6—C7—C2124.0 (2)F1—C18—C17118.2 (2)
C1—C8—O1110.88 (17)C19—C18—C17123.52 (19)
C1—C8—C9133.00 (18)C18—C19—C20117.88 (19)
O1—C8—C9116.11 (17)C18—C19—H19121.1
C14—C9—C10119.4 (2)C20—C19—H19121.1
C14—C9—C8120.44 (19)C15—C20—C19119.95 (19)
C10—C9—C8120.11 (18)C15—C20—H20120.0
C11—C10—C9119.7 (2)C19—C20—H20120.0
O2—S1—C1—C8−127.11 (17)C7—O1—C8—C9179.50 (16)
C15—S1—C1—C8122.87 (17)C1—C8—C9—C14−41.0 (3)
O2—S1—C1—C236.4 (2)O1—C8—C9—C14138.82 (19)
C15—S1—C1—C2−73.58 (19)C1—C8—C9—C10138.7 (2)
C8—C1—C2—C70.7 (2)O1—C8—C9—C10−41.5 (3)
S1—C1—C2—C7−164.98 (15)C14—C9—C10—C111.4 (3)
C8—C1—C2—C3−179.8 (2)C8—C9—C10—C11−178.28 (19)
S1—C1—C2—C314.5 (3)C9—C10—C11—C12−1.7 (3)
C7—C2—C3—C4−0.1 (3)C10—C11—C12—C130.9 (4)
C1—C2—C3—C4−179.5 (2)C11—C12—C13—C140.1 (4)
C2—C3—C4—C50.2 (3)C12—C13—C14—C9−0.4 (3)
C2—C3—C4—Br1179.60 (14)C10—C9—C14—C13−0.4 (3)
C3—C4—C5—C60.1 (3)C8—C9—C14—C13179.3 (2)
Br1—C4—C5—C6−179.34 (16)O2—S1—C15—C2040.06 (17)
C4—C5—C6—C7−0.5 (3)C1—S1—C15—C20151.62 (15)
C8—O1—C7—C6−179.2 (2)O2—S1—C15—C16−146.37 (18)
C8—O1—C7—C21.1 (2)C1—S1—C15—C16−34.81 (19)
C5—C6—C7—O1−179.01 (19)C20—C15—C16—C17−0.2 (3)
C5—C6—C7—C20.6 (3)S1—C15—C16—C17−173.42 (17)
C3—C2—C7—O1179.31 (17)C15—C16—C17—C180.4 (3)
C1—C2—C7—O1−1.1 (2)C16—C17—C18—F1−179.9 (2)
C3—C2—C7—C6−0.4 (3)C16—C17—C18—C19−0.6 (4)
C1—C2—C7—C6179.24 (19)F1—C18—C19—C20179.91 (19)
C2—C1—C8—O10.0 (2)C17—C18—C19—C200.7 (4)
S1—C1—C8—O1166.47 (13)C16—C15—C20—C190.2 (3)
C2—C1—C8—C9179.8 (2)S1—C15—C20—C19173.95 (16)
S1—C1—C8—C9−13.7 (3)C18—C19—C20—C15−0.4 (3)
C7—O1—C8—C1−0.6 (2)
D—H···AD—HH···AD···AD—H···A
C10—H10···O2i0.952.413.341 (3)167
C19—H19···O1ii0.952.503.447 (2)175
C16—H16···Cgiii0.952.993.832 (2)148
Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 phenyl ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C10—H10⋯O2i 0.952.413.341 (3)167
C19—H19⋯O1ii 0.952.503.447 (2)175
C16—H16⋯Cg iii 0.952.993.832 (2)148

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

  3 in total

1.  A short history of SHELX.

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

2.  5-Bromo-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-03

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

Authors:  Pil Ja Seo; Hong Dae Choi; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-17
  3 in total

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