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The title compound, C19H14O2S, was prepared by oxidation of 1-methyl­sulfanyl-2-phenyl­naphtho[2,1-b]furan using 3-chloro­perbenzoic acid. The naphthofuran ring system is approximately planar. The crystal structure includes aromatic π–π stacking and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048240/bi2098sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048240/bi2098Isup2.hkl
Contains datablock I

CCDC reference: 629444

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.046
  • wR factor = 0.114
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

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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 III (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C19H14O2SF(000) = 640
Mr = 306.36Dx = 1.407 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4941 reflections
a = 10.868 (1) Åθ = 2.5–28.3°
b = 9.410 (1) ŵ = 0.23 mm1
c = 14.190 (2) ÅT = 173 K
β = 94.568 (2)°Plate, colourless
V = 1446.6 (3) Å30.52 × 0.34 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
2751 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 27.0°, θmin = 2.3°
φ and ω scansh = 913
8612 measured reflectionsk = 1112
3151 independent reflectionsl = 1816
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) = 0.114H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0417P)2 + 1.0385P]
where P = (Fo2 + 2Fc2)/3
3151 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.37 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
S0.22562 (4)0.25676 (5)0.52687 (3)0.02456 (14)
O10.13002 (12)0.57658 (14)0.35901 (9)0.0264 (3)
O20.30767 (13)0.15046 (15)0.48484 (10)0.0318 (3)
C10.16516 (16)0.3684 (2)0.43463 (12)0.0212 (4)
C20.12569 (16)0.3368 (2)0.33632 (13)0.0236 (4)
C30.10200 (17)0.2116 (2)0.28006 (13)0.0245 (4)
C40.12240 (18)0.0706 (2)0.31168 (14)0.0284 (4)
H40.15630.05440.37300.034*
C50.09293 (19)0.0430 (2)0.25336 (15)0.0339 (5)
H50.10700.13510.27550.041*
C60.0416 (2)0.0207 (3)0.16030 (15)0.0367 (5)
H60.01990.09790.12160.044*
C70.02375 (19)0.1138 (3)0.12689 (15)0.0344 (5)
H70.00910.12720.06500.041*
C80.05409 (17)0.2341 (2)0.18418 (14)0.0288 (4)
C90.03831 (19)0.3745 (2)0.14708 (14)0.0317 (5)
H90.00870.38560.08420.038*
C100.06484 (18)0.4923 (2)0.20002 (14)0.0301 (4)
H100.05620.58330.17490.036*
C110.10620 (17)0.4684 (2)0.29508 (13)0.0255 (4)
C120.16572 (16)0.5130 (2)0.44424 (13)0.0232 (4)
C130.19585 (16)0.6094 (2)0.52321 (13)0.0231 (4)
C140.24706 (18)0.7429 (2)0.50751 (15)0.0285 (4)
H140.26010.77100.44630.034*
C150.2784 (2)0.8332 (2)0.58248 (16)0.0346 (5)
H150.31330.92140.57150.042*
C160.2580 (2)0.7929 (2)0.67383 (16)0.0375 (5)
H160.27970.85360.72410.045*
C170.2053 (2)0.6623 (2)0.69021 (15)0.0335 (5)
H170.19090.63580.75150.040*
C180.17390 (18)0.5714 (2)0.61588 (14)0.0273 (4)
H180.13790.48410.62740.033*
C190.0858 (2)0.1667 (2)0.55185 (16)0.0343 (5)
H19A0.10350.09970.60220.051*
H19B0.05270.11730.49630.051*
H19C0.02660.23490.57040.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0281 (3)0.0212 (2)0.0238 (2)0.00097 (18)0.00103 (18)0.00331 (18)
O10.0313 (7)0.0214 (7)0.0262 (7)0.0006 (5)0.0008 (5)0.0043 (5)
O20.0314 (7)0.0286 (8)0.0348 (8)0.0074 (6)0.0004 (6)0.0017 (6)
C10.0216 (8)0.0209 (9)0.0208 (8)0.0004 (7)0.0009 (7)0.0028 (7)
C20.0202 (9)0.0265 (10)0.0239 (9)0.0002 (7)0.0005 (7)0.0031 (8)
C30.0205 (9)0.0283 (10)0.0249 (9)0.0008 (7)0.0026 (7)0.0022 (8)
C40.0294 (10)0.0290 (11)0.0270 (10)0.0018 (8)0.0025 (8)0.0020 (8)
C50.0360 (11)0.0289 (11)0.0377 (11)0.0032 (9)0.0089 (9)0.0056 (9)
C60.0368 (11)0.0389 (12)0.0347 (11)0.0078 (10)0.0057 (9)0.0157 (10)
C70.0306 (10)0.0471 (13)0.0252 (10)0.0021 (9)0.0005 (8)0.0080 (9)
C80.0234 (9)0.0382 (12)0.0248 (9)0.0012 (8)0.0025 (7)0.0034 (8)
C90.0296 (10)0.0429 (12)0.0220 (9)0.0057 (9)0.0014 (8)0.0031 (9)
C100.0312 (10)0.0320 (11)0.0270 (10)0.0038 (8)0.0016 (8)0.0087 (8)
C110.0242 (9)0.0257 (10)0.0268 (9)0.0006 (8)0.0035 (7)0.0011 (8)
C120.0227 (9)0.0228 (9)0.0241 (9)0.0003 (7)0.0027 (7)0.0055 (7)
C130.0211 (9)0.0194 (9)0.0290 (9)0.0009 (7)0.0025 (7)0.0009 (7)
C140.0291 (10)0.0220 (10)0.0348 (10)0.0005 (8)0.0045 (8)0.0049 (8)
C150.0379 (11)0.0196 (10)0.0460 (12)0.0040 (8)0.0008 (9)0.0008 (9)
C160.0452 (13)0.0268 (11)0.0397 (12)0.0010 (9)0.0016 (10)0.0101 (9)
C170.0418 (12)0.0314 (11)0.0281 (10)0.0006 (9)0.0072 (9)0.0028 (9)
C180.0304 (10)0.0210 (10)0.0311 (10)0.0019 (8)0.0063 (8)0.0008 (8)
C190.0367 (11)0.0281 (11)0.0394 (12)0.0024 (9)0.0112 (9)0.0070 (9)
Geometric parameters (Å, º) top
S—O21.4954 (15)C9—C101.357 (3)
S—C11.7641 (18)C9—H90.930
S—C191.800 (2)C10—C111.406 (3)
O1—C111.374 (2)C10—H100.930
O1—C121.377 (2)C12—C131.459 (3)
C1—C121.367 (3)C13—C141.399 (3)
C1—C21.457 (2)C13—C181.402 (3)
C2—C111.379 (3)C14—C151.383 (3)
C2—C31.435 (3)C14—H140.930
C3—C41.413 (3)C15—C161.385 (3)
C3—C81.433 (3)C15—H150.930
C4—C51.374 (3)C16—C171.383 (3)
C4—H40.930C16—H160.930
C5—C61.408 (3)C17—C181.379 (3)
C5—H50.930C17—H170.930
C6—C71.360 (3)C18—H180.930
C6—H60.930C19—H19A0.960
C7—C81.417 (3)C19—H19B0.960
C7—H70.930C19—H19C0.960
C8—C91.427 (3)
O2—S—C1107.53 (8)C9—C10—H10122.0
O2—S—C19107.64 (10)C11—C10—H10122.0
C1—S—C1998.99 (9)O1—C11—C2111.76 (16)
C11—O1—C12106.44 (14)O1—C11—C10122.97 (18)
C12—C1—C2107.31 (16)C2—C11—C10125.27 (19)
C12—C1—S121.35 (14)C1—C12—O1110.24 (16)
C2—C1—S130.72 (14)C1—C12—C13133.99 (17)
C11—C2—C3119.11 (17)O1—C12—C13115.77 (16)
C11—C2—C1104.25 (16)C14—C13—C18118.57 (18)
C3—C2—C1136.61 (17)C14—C13—C12120.27 (17)
C4—C3—C8118.44 (18)C18—C13—C12121.17 (17)
C4—C3—C2125.29 (17)C15—C14—C13120.42 (19)
C8—C3—C2116.27 (18)C15—C14—H14119.8
C5—C4—C3121.09 (19)C13—C14—H14119.8
C5—C4—H4119.5C14—C15—C16120.21 (19)
C3—C4—H4119.5C14—C15—H15119.9
C4—C5—C6120.3 (2)C16—C15—H15119.9
C4—C5—H5119.8C17—C16—C15120.0 (2)
C6—C5—H5119.8C17—C16—H16120.0
C7—C6—C5120.1 (2)C15—C16—H16120.0
C7—C6—H6120.0C18—C17—C16120.2 (2)
C5—C6—H6120.0C18—C17—H17119.9
C6—C7—C8121.54 (19)C16—C17—H17119.9
C6—C7—H7119.2C17—C18—C13120.61 (19)
C8—C7—H7119.2C17—C18—H18119.7
C7—C8—C9120.79 (18)C13—C18—H18119.7
C7—C8—C3118.49 (19)S—C19—H19A109.5
C9—C8—C3120.72 (18)S—C19—H19B109.5
C10—C9—C8122.53 (18)H19A—C19—H19B109.5
C10—C9—H9118.7S—C19—H19C109.5
C8—C9—H9118.7H19A—C19—H19C109.5
C9—C10—C11116.00 (19)H19B—C19—H19C109.5
O2—S—C1—C12132.55 (16)C12—O1—C11—C20.1 (2)
C19—S—C1—C12115.63 (17)C12—O1—C11—C10178.74 (18)
O2—S—C1—C237.20 (19)C3—C2—C11—O1178.39 (16)
C19—S—C1—C274.62 (19)C1—C2—C11—O10.0 (2)
C12—C1—C2—C110.2 (2)C3—C2—C11—C100.5 (3)
S—C1—C2—C11170.63 (15)C1—C2—C11—C10178.89 (18)
C12—C1—C2—C3177.8 (2)C9—C10—C11—O1176.18 (17)
S—C1—C2—C311.4 (3)C9—C10—C11—C22.6 (3)
C11—C2—C3—C4177.35 (19)C2—C1—C12—O10.3 (2)
C1—C2—C3—C44.9 (3)S—C1—C12—O1171.57 (12)
C11—C2—C3—C82.5 (3)C2—C1—C12—C13179.95 (19)
C1—C2—C3—C8175.3 (2)S—C1—C12—C138.1 (3)
C8—C3—C4—C52.4 (3)C11—O1—C12—C10.3 (2)
C2—C3—C4—C5177.78 (19)C11—O1—C12—C13180.00 (15)
C3—C4—C5—C60.1 (3)C1—C12—C13—C14147.9 (2)
C4—C5—C6—C71.6 (3)O1—C12—C13—C1431.8 (2)
C5—C6—C7—C80.9 (3)C1—C12—C13—C1832.5 (3)
C6—C7—C8—C9178.0 (2)O1—C12—C13—C18147.91 (17)
C6—C7—C8—C31.4 (3)C18—C13—C14—C151.8 (3)
C4—C3—C8—C73.0 (3)C12—C13—C14—C15178.48 (18)
C2—C3—C8—C7177.13 (17)C13—C14—C15—C160.8 (3)
C4—C3—C8—C9176.46 (18)C14—C15—C16—C170.5 (3)
C2—C3—C8—C93.4 (3)C15—C16—C17—C180.6 (3)
C7—C8—C9—C10179.1 (2)C16—C17—C18—C130.5 (3)
C3—C8—C9—C101.4 (3)C14—C13—C18—C171.7 (3)
C8—C9—C10—C111.6 (3)C12—C13—C18—C17178.60 (18)
 

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