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The title compound, C21H16OS, was prepared by the Lewis acid-catalysed reaction of 4-phenyl­phenol with 2-chloro-2-(methyl­sulfan­yl)acetophenone. The 1-benzofuran ring system is almost planar. The structure is stabilized by inter­molecular aromatic π–π inter­actions between the benzene rings of the benzofuran group and by C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039596/sj2122sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039596/sj2122Isup2.hkl
Contains datablock I

CCDC reference: 628397

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.113
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm
Author Response: The Beam size is 0.8 mm.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio

Alert level G PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

3-Methylsulfanyl-2,5-diphenyl-1-benzofuran top
Crystal data top
C21H16OSZ = 2
Mr = 316.40F(000) = 332
Triclinic, P1Dx = 1.304 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2050 (6) ÅCell parameters from 4323 reflections
b = 9.4362 (6) Åθ = 2.5–28.3°
c = 11.5415 (7) ŵ = 0.20 mm1
α = 112.690 (1)°T = 120 K
β = 94.296 (1)°Block, colorless
γ = 114.764 (1)°0.62 × 0.60 × 0.54 mm
V = 805.70 (9) Å3
Data collection top
Bruker SMART CCD
diffractometer
2952 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
Graphite monochromatorθmax = 27.0°, θmin = 2.0°
Detector resolution: 10.00 pixels mm-1h = 1111
φ and ω scansk = 1211
6966 measured reflectionsl = 1414
3443 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0357P)2 + 0.4767P]
where P = (Fo2 + 2Fc2)/3
3443 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.37 e Å3
Special details top

Experimental. Spectroscopic analysis: 1H NMR (CDCl3): δ 2.40 (s, 3H), 7.33–7.43 (m, 2H), 7.44–7.52 (m, 4H), 7.56 (s, 2H), 7.67 (d, J = 7.20 Hz, 2H), 7.90 (s, 1H), 8.31 (d, J = 7.52 Hz, 2H); 13C NMR (CDCl3): δ 18.5, 109.3, 111.5, 118.4, 124.7, 127.0, 127.2, 127.5, 128.5, 128.8, 129.1, 130.2, 131.7, 136.9, 141.5, 153.3, 155.9; MS: 316 [M+].

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.76159 (6)0.58822 (5)0.56992 (5)0.03169 (14)
O0.46634 (16)0.09758 (15)0.29129 (12)0.0301 (3)
C10.8153 (3)0.3540 (3)0.0432 (2)0.0365 (4)
H10.86240.37110.02200.044*
C20.8211 (3)0.4948 (3)0.1487 (2)0.0367 (4)
H20.87300.60640.15420.044*
C30.7503 (2)0.4701 (2)0.24532 (19)0.0320 (4)
H30.75460.56520.31530.038*
C40.6721 (2)0.3029 (2)0.23873 (18)0.0270 (4)
C50.6681 (2)0.1623 (2)0.13207 (18)0.0300 (4)
H50.61690.05040.12610.036*
C60.7391 (2)0.1882 (2)0.03598 (19)0.0343 (4)
H60.73580.09380.03400.041*
C70.5931 (2)0.2691 (2)0.33731 (18)0.0273 (4)
C80.6145 (2)0.3662 (2)0.46682 (17)0.0253 (4)
C90.4949 (2)0.2500 (2)0.50716 (17)0.0248 (4)
C100.4515 (2)0.2679 (2)0.62262 (17)0.0265 (4)
H100.50810.37510.69810.032*
C110.3215 (2)0.1227 (2)0.62402 (18)0.0276 (4)
C120.2384 (2)0.0400 (2)0.50777 (19)0.0310 (4)
H120.15240.13640.50930.037*
C130.2807 (2)0.0599 (2)0.39302 (18)0.0314 (4)
H130.22610.16710.31750.038*
C140.4086 (2)0.0874 (2)0.39533 (17)0.0281 (4)
C150.2671 (2)0.1392 (2)0.74441 (18)0.0291 (4)
C160.3819 (3)0.2457 (2)0.86862 (19)0.0349 (4)
H160.49500.30540.87660.042*
C170.3283 (3)0.2630 (3)0.9802 (2)0.0433 (5)
H170.40570.33411.06240.052*
C180.1601 (3)0.1747 (3)0.9696 (2)0.0455 (6)
H180.12440.18711.04440.055*
C190.0455 (3)0.0682 (3)0.8473 (2)0.0424 (5)
H190.06750.00850.83990.051*
C200.0981 (3)0.0501 (2)0.7358 (2)0.0340 (4)
H200.01990.02230.65400.041*
C210.8985 (3)0.5597 (3)0.6668 (3)0.0622 (8)
H21A0.83700.49570.71000.093*
H21B0.98680.67280.73110.093*
H21C0.94510.49550.61120.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0301 (3)0.0219 (2)0.0334 (3)0.00902 (18)0.00133 (19)0.00917 (18)
O0.0307 (7)0.0251 (6)0.0265 (6)0.0101 (5)0.0062 (5)0.0088 (5)
C10.0346 (10)0.0434 (11)0.0343 (10)0.0167 (9)0.0127 (9)0.0225 (9)
C20.0377 (11)0.0337 (10)0.0465 (12)0.0176 (9)0.0130 (9)0.0254 (9)
C30.0359 (10)0.0300 (9)0.0362 (10)0.0204 (8)0.0099 (8)0.0158 (8)
C40.0253 (9)0.0282 (9)0.0289 (9)0.0145 (7)0.0053 (7)0.0132 (7)
C50.0285 (9)0.0251 (8)0.0307 (9)0.0102 (7)0.0046 (7)0.0114 (7)
C60.0317 (10)0.0326 (10)0.0297 (10)0.0133 (8)0.0064 (8)0.0092 (8)
C70.0244 (9)0.0235 (8)0.0324 (9)0.0118 (7)0.0037 (7)0.0120 (7)
C80.0226 (8)0.0219 (8)0.0284 (9)0.0107 (7)0.0032 (7)0.0095 (7)
C90.0220 (8)0.0221 (8)0.0281 (9)0.0117 (7)0.0025 (7)0.0093 (7)
C100.0265 (9)0.0222 (8)0.0276 (9)0.0130 (7)0.0037 (7)0.0077 (7)
C110.0292 (9)0.0285 (9)0.0299 (9)0.0179 (7)0.0076 (7)0.0137 (7)
C120.0301 (10)0.0236 (8)0.0373 (10)0.0115 (7)0.0095 (8)0.0139 (8)
C130.0319 (10)0.0225 (8)0.0307 (9)0.0103 (7)0.0047 (8)0.0078 (7)
C140.0298 (9)0.0270 (9)0.0259 (9)0.0146 (7)0.0053 (7)0.0103 (7)
C150.0379 (10)0.0252 (8)0.0332 (9)0.0196 (8)0.0137 (8)0.0165 (7)
C160.0435 (11)0.0299 (9)0.0366 (10)0.0201 (9)0.0110 (9)0.0176 (8)
C170.0687 (16)0.0341 (10)0.0327 (10)0.0283 (10)0.0124 (10)0.0174 (9)
C180.0776 (17)0.0378 (11)0.0410 (12)0.0333 (11)0.0334 (12)0.0277 (10)
C190.0524 (13)0.0344 (10)0.0530 (13)0.0228 (10)0.0289 (11)0.0274 (10)
C200.0398 (11)0.0270 (9)0.0393 (11)0.0172 (8)0.0140 (9)0.0175 (8)
C210.0464 (14)0.0404 (12)0.0686 (17)0.0159 (11)0.0230 (13)0.0089 (11)
Geometric parameters (Å, º) top
S—C81.760 (2)C10—H100.9300
S—C211.793 (2)C11—C121.420 (2)
O—C141.370 (2)C11—C151.486 (3)
O—C71.387 (2)C12—C131.374 (3)
C1—C61.385 (3)C12—H120.9300
C1—C21.391 (3)C13—C141.383 (3)
C1—H10.9300C13—H130.9300
C2—C31.379 (3)C15—C161.398 (3)
C2—H20.9300C15—C201.398 (3)
C3—C41.400 (2)C16—C171.389 (3)
C3—H30.9300C16—H160.9300
C4—C51.403 (3)C17—C181.385 (3)
C4—C71.461 (3)C17—H170.9300
C5—C61.379 (3)C18—C191.382 (3)
C5—H50.9300C18—H180.9300
C6—H60.9300C19—C201.382 (3)
C7—C81.364 (3)C19—H190.9300
C8—C91.446 (2)C20—H200.9300
C9—C101.388 (3)C21—H21A0.9600
C9—C141.396 (2)C21—H21B0.9600
C10—C111.398 (2)C21—H21C0.9600
C8—S—C2199.39 (9)C12—C11—C15120.1 (2)
C14—O—C7106.6 (1)C13—C12—C11122.2 (2)
C6—C1—C2119.6 (2)C13—C12—H12118.9
C6—C1—H1120.2C11—C12—H12118.9
C2—C1—H1120.2C12—C13—C14116.8 (2)
C3—C2—C1120.5 (2)C12—C13—H13121.6
C3—C2—H2119.7C14—C13—H13121.6
C1—C2—H2119.7O—C14—C13126.2 (2)
C2—C3—C4120.5 (2)O—C14—C9110.6 (2)
C2—C3—H3119.8C13—C14—C9123.3 (2)
C4—C3—H3119.8C16—C15—C20118.3 (2)
C3—C4—C5118.4 (2)C16—C15—C11121.3 (2)
C3—C4—C7122.7 (2)C20—C15—C11120.4 (2)
C5—C4—C7119.0 (2)C17—C16—C15120.5 (2)
C6—C5—C4120.8 (2)C17—C16—H16119.7
C6—C5—H5119.6C15—C16—H16119.7
C4—C5—H5119.6C18—C17—C16120.3 (2)
C5—C6—C1120.3 (2)C18—C17—H17119.9
C5—C6—H6119.9C16—C17—H17119.9
C1—C6—H6119.9C19—C18—C17119.7 (2)
C8—C7—O110.6 (2)C19—C18—H18120.1
C8—C7—C4135.3 (2)C17—C18—H18120.1
O—C7—C4114.1 (2)C18—C19—C20120.3 (2)
C7—C8—C9106.8 (2)C18—C19—H19119.9
C7—C8—S127.9 (1)C20—C19—H19119.9
C9—C8—S125.2 (1)C19—C20—C15120.9 (2)
C10—C9—C14119.3 (2)C19—C20—H20119.5
C10—C9—C8135.3 (2)C15—C20—H20119.5
C14—C9—C8105.4 (2)S—C21—H21A109.5
C9—C10—C11119.2 (2)S—C21—H21B109.5
C9—C10—H10120.4H21A—C21—H21B109.5
C11—C10—H10120.4S—C21—H21C109.5
C10—C11—C12119.3 (2)H21A—C21—H21C109.5
C10—C11—C15120.6 (2)H21B—C21—H21C109.5
C6—C1—C2—C30.5 (3)C9—C10—C11—C120.7 (2)
C1—C2—C3—C40.2 (3)C9—C10—C11—C15177.4 (2)
C2—C3—C4—C50.1 (3)C10—C11—C12—C130.3 (3)
C2—C3—C4—C7179.1 (2)C15—C11—C12—C13177.8 (2)
C3—C4—C5—C60.1 (3)C11—C12—C13—C140.4 (3)
C7—C4—C5—C6179.1 (2)C7—O—C14—C13179.4 (2)
C4—C5—C6—C10.2 (3)C7—O—C14—C90.60 (19)
C2—C1—C6—C50.6 (3)C12—C13—C14—O177.8 (2)
C14—O—C7—C80.6 (2)C12—C13—C14—C90.8 (3)
C14—O—C7—C4178.8 (1)C10—C9—C14—O178.4 (1)
C3—C4—C7—C826.9 (3)C10—C9—C14—C130.5 (3)
C5—C4—C7—C8153.9 (2)C8—C9—C14—C13179.2 (2)
C3—C4—C7—O153.9 (2)C10—C11—C15—C1637.1 (2)
C5—C4—C7—O25.3 (2)C12—C11—C15—C16144.8 (2)
O—C7—C8—C90.38 (19)C10—C11—C15—C20141.7 (2)
C4—C7—C8—C9178.9 (2)C12—C11—C15—C2036.4 (2)
O—C7—C8—S178.6 (1)C20—C15—C16—C170.5 (3)
C4—C7—C8—S0.7 (3)C11—C15—C16—C17178.4 (2)
C21—S—C8—C7107.4 (2)C15—C16—C17—C180.0 (3)
C21—S—C8—C970.5 (2)C16—C17—C18—C190.4 (3)
C7—C8—C9—C10178.4 (2)C17—C18—C19—C200.3 (3)
S—C8—C9—C103.3 (3)C18—C19—C20—C150.3 (3)
S—C8—C9—C14178.3 (1)C16—C15—C20—C190.6 (3)
C14—C9—C10—C110.3 (2)C11—C15—C20—C19178.2 (2)
C8—C9—C10—C11177.9 (2)
 

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