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The title compound, C15H11ClO2S, was prepared by the oxidation of 5-chloro-3-methyl­sulfanyl-2-phenyl-1-benzofuran using 3-chloro­perbenzoic acid. The 1-benzofuran ring system is almost planar. The crystal structure is stabilized by weak aromatic π–π stacking and –CH2—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006502/gw2002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006502/gw2002Isup2.hkl
Contains datablock I

CCDC reference: 640336

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.078
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

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Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl .. O2 .. 3.26 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 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 2 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: SAINT (Bruker, 1997); data reduction: SAINT; 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.

5-Chloro-3-methylsulfinyl-2-phenyl-1-benzofuran top
Crystal data top
C15H11ClO2SZ = 2
Mr = 290.75F(000) = 300
Triclinic, P1Dx = 1.488 Mg m3
Hall symbol: -p_1Mo Kα radiation, λ = 0.71073 Å
a = 8.1519 (5) ÅCell parameters from 4954 reflections
b = 8.2258 (5) Åθ = 2.7–28.3°
c = 10.6247 (6) ŵ = 0.45 mm1
α = 91.195 (1)°T = 173 K
β = 95.882 (1)°Block, colourless
γ = 113.439 (1)°0.65 × 0.43 × 0.25 mm
V = 648.74 (7) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2484 independent reflections
Radiation source: fine-focus sealed tube2373 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
Detector resolution: 10.00 pixels mm-1θmax = 26.0°, θmin = 1.9°
φ and ω scansh = 1010
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1999)
k = 1010
Tmin = 0.792, Tmax = 0.895l = 1313
5026 measured 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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0358P)2 + 0.3256P]
where P = (Fo2 + 2Fc2)/3
2484 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.38 e Å3
Special details top

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
S0.20670 (5)0.18486 (5)0.09441 (3)0.02258 (11)
Cl0.79813 (5)0.60605 (6)0.51988 (3)0.03201 (12)
O10.69955 (13)0.34529 (14)0.00775 (10)0.0231 (2)
O20.17903 (15)0.32055 (15)0.17488 (12)0.0329 (3)
C10.43980 (19)0.26649 (19)0.07956 (13)0.0205 (3)
C20.58546 (19)0.37345 (19)0.17477 (14)0.0205 (3)
C30.5999 (2)0.43216 (19)0.30166 (14)0.0225 (3)
H30.49900.40480.34430.027*
C40.7715 (2)0.5329 (2)0.36050 (14)0.0237 (3)
C50.9265 (2)0.5776 (2)0.29882 (15)0.0260 (3)
H51.03890.64610.34260.031*
C60.9130 (2)0.5202 (2)0.17334 (15)0.0252 (3)
H61.01380.54840.13060.030*
C70.74121 (19)0.41883 (19)0.11499 (14)0.0216 (3)
C80.51487 (19)0.25412 (19)0.02768 (14)0.0213 (3)
C90.44204 (19)0.16598 (19)0.15405 (14)0.0218 (3)
C100.2880 (2)0.0077 (2)0.17214 (15)0.0262 (3)
H100.23140.04380.10270.031*
C110.2186 (2)0.0733 (2)0.29283 (16)0.0311 (4)
H110.11500.17790.30430.037*
C120.3042 (2)0.0020 (2)0.39622 (16)0.0332 (4)
H120.25760.05190.47720.040*
C130.4599 (2)0.1583 (2)0.37933 (15)0.0306 (3)
H130.51760.20720.44900.037*
C140.5293 (2)0.2411 (2)0.25942 (14)0.0248 (3)
H140.63280.34580.24850.030*
C150.1957 (2)0.0090 (2)0.19507 (18)0.0356 (4)
H15A0.07430.05240.21390.053*
H15B0.27410.05810.27250.053*
H15C0.23270.07260.15260.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.01645 (19)0.0242 (2)0.0261 (2)0.00674 (14)0.00386 (14)0.00235 (14)
Cl0.0309 (2)0.0409 (2)0.0215 (2)0.01326 (17)0.00215 (15)0.00526 (15)
O10.0186 (5)0.0267 (5)0.0216 (5)0.0063 (4)0.0047 (4)0.0002 (4)
O20.0280 (6)0.0284 (6)0.0454 (7)0.0123 (5)0.0142 (5)0.0008 (5)
C10.0178 (7)0.0218 (7)0.0208 (7)0.0067 (5)0.0029 (5)0.0018 (5)
C20.0180 (7)0.0203 (7)0.0236 (7)0.0078 (5)0.0033 (5)0.0029 (5)
C30.0216 (7)0.0253 (7)0.0221 (7)0.0105 (6)0.0045 (6)0.0022 (6)
C40.0262 (8)0.0251 (7)0.0204 (7)0.0115 (6)0.0009 (6)0.0000 (6)
C50.0198 (7)0.0248 (7)0.0298 (8)0.0063 (6)0.0012 (6)0.0006 (6)
C60.0188 (7)0.0261 (8)0.0290 (8)0.0067 (6)0.0056 (6)0.0023 (6)
C70.0217 (7)0.0229 (7)0.0208 (7)0.0094 (6)0.0043 (6)0.0022 (5)
C80.0184 (7)0.0205 (7)0.0240 (7)0.0066 (6)0.0035 (5)0.0033 (5)
C90.0233 (7)0.0233 (7)0.0216 (7)0.0121 (6)0.0035 (6)0.0009 (5)
C100.0273 (8)0.0248 (8)0.0258 (8)0.0090 (6)0.0052 (6)0.0013 (6)
C110.0308 (8)0.0263 (8)0.0321 (8)0.0083 (7)0.0007 (7)0.0037 (6)
C120.0409 (9)0.0356 (9)0.0233 (8)0.0168 (7)0.0007 (7)0.0057 (6)
C130.0377 (9)0.0354 (9)0.0220 (7)0.0171 (7)0.0070 (6)0.0038 (6)
C140.0257 (7)0.0254 (7)0.0251 (7)0.0114 (6)0.0054 (6)0.0034 (6)
C150.0312 (9)0.0305 (9)0.0477 (10)0.0121 (7)0.0147 (8)0.0157 (7)
Geometric parameters (Å, º) top
S—O21.493 (1)C6—H60.9300
S—C11.771 (1)C8—C91.461 (2)
S—C151.796 (2)C9—C101.395 (2)
Cl—C41.748 (2)C9—C141.408 (2)
O1—C71.377 (2)C10—C111.387 (2)
O1—C81.380 (2C10—H100.9300
C1—C81.368 (2)C11—C121.385 (2)
C1—C21.447 (2)C11—H110.9300
C2—C71.397 (2)C12—C131.393 (2)
C2—C31.400 (2)C12—H120.9300
C3—C41.383 (2)C13—C141.384 (2)
C3—H30.9300C13—H130.9300
C4—C51.404 (2)C14—H140.9300
C5—C61.384 (2)C15—H15A0.9600
C5—H50.9300C15—H15B0.9600
C6—C71.383 (2)C15—H15C0.9600
O2—S—C1107.06 (7)C1—C8—C9134.0 (1)
O2—S—C15105.94 (8)O1—C8—C9115.5 (1)
C1—S—C1597.64 (7)C10—C9—C14119.4 (1)
C7—O1—C8106.7 (1)C10—C9—C8121.1 (1)
C8—C1—C2107.2 (1)C14—C9—C8119.5 (1)
C8—C1—S126.3 (1)C11—C10—C9120.6 (2)
C2—C1—S126.3 (1)C11—C10—H10119.7
C7—C2—C3119.4 (1)C9—C10—H10119.7
C7—C2—C1105.0 (1)C12—C11—C10119.8 (2)
C3—C2—C1135.6 (1)C12—C11—H11120.1
C4—C3—C2116.7 (1)C10—C11—H11120.1
C4—C3—H3121.6C11—C12—C13120.3 (2)
C2—C3—H3121.6C11—C12—H12119.9
C3—C4—C5123.1 (1)C13—C12—H12119.9
C3—C4—Cl118.7 (1)C14—C13—C12120.4 (2)
C5—C4—Cl118.2 (1)C14—C13—H13119.8
C6—C5—C4120.4 (1)C12—C13—H13119.8
C6—C5—H5119.8C13—C14—C9119.6 (1)
C4—C5—H5119.8C13—C14—H14120.2
C7—C6—C5116.3 (1)C9—C14—H14120.2
C7—C6—H6121.9S—C15—H15A109.5
C5—C6—H6121.9S—C15—H15B109.5
O1—C7—C6125.3 (1)H15A—C15—H15B109.5
O1—C7—C2110.6 (1)S—C15—H15C109.5
C6—C7—C2124.1 (1)H15A—C15—H15C109.5
C1—C8—O1110.6 (1)H15B—C15—H15C109.5
O2—S—C1—C8139.9 (1)C2—C1—C8—O10.3 (2)
C15—S—C1—C8110.7 (2)S—C1—C8—O1174.9 (1)
O2—S—C1—C233.6 (1)C2—C1—C8—C9179.7 (2)
C15—S—C1—C275.7 (1)S—C1—C8—C95.7 (3)
S—C1—C2—C7174.3 (1)C7—O1—C8—C9179.7 (1)
C8—C1—C2—C3178.8 (2)C1—C8—C9—C1031.6 (2)
S—C1—C2—C36.6 (2)O1—C8—C9—C10147.8 (1)
C1—C2—C3—C4178.7 (2)C1—C8—C9—C14148.9 (2)
C2—C3—C4—C50.4 (2)O1—C8—C9—C1431.7 (2)
C2—C3—C4—Cl178.7 (1)C14—C9—C10—C111.4 (2)
C3—C4—C5—C60.3 (2)C8—C9—C10—C11179.0 (1)
Cl—C4—C5—C6178.9 (1)C9—C10—C11—C120.9 (2)
C4—C5—C6—C70.1 (2)C10—C11—C12—C130.3 (3)
C8—O1—C7—C6179.5 (1)C11—C12—C13—C140.9 (3)
C5—C6—C7—O1178.2 (1)C12—C13—C14—C90.4 (2)
C5—C6—C7—C20.2 (2)C10—C9—C14—C130.8 (2)
C3—C2—C7—O1178.5 (1)C8—C9—C14—C13179.7 (1)
C1—C2—C7—C6179.3 (1)
 

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