organic compounds
2-Phenyl-1-(phenylsulfinyl)naphtho[2,1-b]furan
aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry Pukyong National University 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr
In the title compound, C24H16O2S, the O atom and the phenyl group of the phenylsulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment; the phenyl ring is almost perpendicular to this plane [82.34 (5)°]. The 2-phenyl ring is rotated out of the naphthofuran plane making a dihedral angle of 48.21 (6)°. The shows π–π interactions between the central benzene rings of adjacent molecules [centroid–centroid distance = 3.516 (3) Å], as well as non-classical C—H⋯O hydrogen bonds.
Related literature
For the crystal structures of similar naphtho[2,1-b]furan derivatives, see: Choi et al. (2007, 2008). For the biological and pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004); Hagiwara et al. (1999); Piloto et al. (2005).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: SMART (Bruker, 2001); cell 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.
Supporting information
10.1107/S1600536809019977/ng2587sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809019977/ng2587Isup2.hkl
The 77% 3-chloroperoxybenzoic acid (77%, 247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2-phenyl-1-(phenylsulfanyl)naphtho[2,1-b]furan (352 mg, 1.0 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by χompound in benzene at room temperature.
(hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 81%, m.p. 462-463 K; Rf = 0.54 (hexane-ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the titleAll H atoms were positioned geometrically and refined using a riding model, with C–H = 0.95 Å for aromatic H atoms and with Uiso(H) = 1.2Ueq (C) for aromatic H atoms.
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).C24H16O2S | Z = 2 |
Mr = 368.43 | F(000) = 384 |
Triclinic, P1 | Dx = 1.359 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2262 (7) Å | Cell parameters from 3903 reflections |
b = 10.3430 (8) Å | θ = 2.2–28.1° |
c = 10.4296 (8) Å | µ = 0.20 mm−1 |
α = 78.298 (1)° | T = 173 K |
β = 86.849 (1)° | Block, colorless |
γ = 67.506 (1)° | 0.30 × 0.20 × 0.10 mm |
V = 900.15 (12) Å3 |
Bruker SMART CCD diffractometer | 2602 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.076 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
Detector resolution: 10.0 pixels mm-1 | h = −10→10 |
ϕ and ω scans | k = −12→12 |
6736 measured reflections | l = −12→12 |
3140 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0292P)2 + 0.4516P] where P = (Fo2 + 2Fc2)/3 |
3140 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C24H16O2S | γ = 67.506 (1)° |
Mr = 368.43 | V = 900.15 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.2262 (7) Å | Mo Kα radiation |
b = 10.3430 (8) Å | µ = 0.20 mm−1 |
c = 10.4296 (8) Å | T = 173 K |
α = 78.298 (1)° | 0.30 × 0.20 × 0.10 mm |
β = 86.849 (1)° |
Bruker SMART CCD diffractometer | 2602 reflections with I > 2σ(I) |
6736 measured reflections | Rint = 0.076 |
3140 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.30 e Å−3 |
3140 reflections | Δρmin = −0.36 e Å−3 |
244 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S | 0.92526 (5) | 0.67298 (6) | 0.63521 (5) | 0.02249 (16) | |
O1 | 0.55628 (15) | 0.80588 (16) | 0.40427 (15) | 0.0287 (4) | |
O2 | 1.01571 (15) | 0.51840 (16) | 0.68794 (15) | 0.0304 (4) | |
C1 | 0.7484 (2) | 0.6976 (2) | 0.5575 (2) | 0.0217 (4) | |
C2 | 0.6230 (2) | 0.6466 (2) | 0.5980 (2) | 0.0225 (5) | |
C3 | 0.5963 (2) | 0.5480 (2) | 0.7043 (2) | 0.0247 (5) | |
C4 | 0.7034 (2) | 0.4667 (2) | 0.8087 (2) | 0.0288 (5) | |
H4 | 0.8013 | 0.4767 | 0.8114 | 0.035* | |
C5 | 0.6685 (3) | 0.3735 (3) | 0.9063 (2) | 0.0369 (6) | |
H5 | 0.7423 | 0.3195 | 0.9760 | 0.044* | |
C6 | 0.5244 (3) | 0.3568 (3) | 0.9045 (3) | 0.0409 (6) | |
H6 | 0.5006 | 0.2928 | 0.9733 | 0.049* | |
C7 | 0.4196 (3) | 0.4323 (3) | 0.8042 (3) | 0.0367 (6) | |
H7 | 0.3231 | 0.4194 | 0.8033 | 0.044* | |
C8 | 0.4506 (2) | 0.5296 (2) | 0.7011 (2) | 0.0304 (5) | |
C9 | 0.3413 (2) | 0.6054 (3) | 0.5950 (3) | 0.0350 (6) | |
H9 | 0.2462 | 0.5900 | 0.5946 | 0.042* | |
C10 | 0.3676 (2) | 0.6990 (3) | 0.4943 (2) | 0.0341 (6) | |
H10 | 0.2936 | 0.7499 | 0.4242 | 0.041* | |
C11 | 0.5109 (2) | 0.7163 (2) | 0.4998 (2) | 0.0265 (5) | |
C12 | 0.7040 (2) | 0.7901 (2) | 0.4412 (2) | 0.0240 (5) | |
C13 | 0.7758 (2) | 0.8777 (2) | 0.3541 (2) | 0.0245 (5) | |
C14 | 0.6902 (3) | 1.0219 (2) | 0.3089 (2) | 0.0310 (5) | |
H14 | 0.5843 | 1.0632 | 0.3339 | 0.037* | |
C15 | 0.7568 (3) | 1.1061 (2) | 0.2284 (2) | 0.0355 (6) | |
H15 | 0.6975 | 1.2049 | 0.1987 | 0.043* | |
C16 | 0.9113 (3) | 1.0456 (3) | 0.1907 (2) | 0.0362 (6) | |
H16 | 0.9579 | 1.1031 | 0.1350 | 0.043* | |
C17 | 0.9966 (3) | 0.9026 (3) | 0.2340 (2) | 0.0332 (5) | |
H17 | 1.1020 | 0.8618 | 0.2076 | 0.040* | |
C18 | 0.9314 (2) | 0.8173 (2) | 0.3153 (2) | 0.0280 (5) | |
H18 | 0.9914 | 0.7185 | 0.3448 | 0.034* | |
C19 | 0.8432 (2) | 0.7532 (2) | 0.7740 (2) | 0.0233 (5) | |
C20 | 0.7332 (2) | 0.8915 (2) | 0.7556 (2) | 0.0296 (5) | |
H20 | 0.6946 | 0.9429 | 0.6700 | 0.036* | |
C21 | 0.6802 (3) | 0.9539 (3) | 0.8632 (3) | 0.0376 (6) | |
H21 | 0.6040 | 1.0485 | 0.8519 | 0.045* | |
C22 | 0.7381 (3) | 0.8787 (3) | 0.9879 (2) | 0.0369 (6) | |
H22 | 0.7005 | 0.9218 | 1.0617 | 0.044* | |
C23 | 0.8501 (3) | 0.7414 (3) | 1.0049 (2) | 0.0344 (5) | |
H23 | 0.8901 | 0.6904 | 1.0901 | 0.041* | |
C24 | 0.9038 (2) | 0.6785 (2) | 0.8972 (2) | 0.0286 (5) | |
H24 | 0.9817 | 0.5846 | 0.9080 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0174 (2) | 0.0248 (3) | 0.0242 (3) | −0.0081 (2) | −0.00033 (18) | −0.0022 (2) |
O1 | 0.0238 (7) | 0.0305 (9) | 0.0299 (9) | −0.0084 (6) | −0.0053 (6) | −0.0044 (7) |
O2 | 0.0223 (7) | 0.0265 (9) | 0.0369 (10) | −0.0036 (6) | −0.0003 (6) | −0.0050 (7) |
C1 | 0.0188 (9) | 0.0223 (11) | 0.0238 (11) | −0.0064 (8) | 0.0017 (8) | −0.0074 (9) |
C2 | 0.0193 (9) | 0.0216 (11) | 0.0274 (12) | −0.0063 (8) | 0.0018 (8) | −0.0095 (9) |
C3 | 0.0232 (10) | 0.0224 (11) | 0.0308 (12) | −0.0091 (8) | 0.0083 (8) | −0.0112 (9) |
C4 | 0.0261 (11) | 0.0277 (12) | 0.0332 (13) | −0.0113 (9) | 0.0050 (9) | −0.0062 (10) |
C5 | 0.0389 (12) | 0.0335 (14) | 0.0367 (14) | −0.0142 (10) | 0.0070 (10) | −0.0046 (11) |
C6 | 0.0474 (14) | 0.0377 (15) | 0.0431 (16) | −0.0235 (12) | 0.0206 (12) | −0.0106 (12) |
C7 | 0.0319 (12) | 0.0411 (15) | 0.0481 (16) | −0.0229 (11) | 0.0184 (11) | −0.0193 (12) |
C8 | 0.0244 (10) | 0.0321 (13) | 0.0389 (14) | −0.0115 (9) | 0.0105 (9) | −0.0172 (11) |
C9 | 0.0197 (10) | 0.0421 (15) | 0.0493 (16) | −0.0135 (10) | 0.0068 (10) | −0.0207 (12) |
C10 | 0.0211 (10) | 0.0397 (14) | 0.0417 (15) | −0.0075 (10) | −0.0035 (9) | −0.0158 (11) |
C11 | 0.0225 (10) | 0.0256 (12) | 0.0316 (13) | −0.0071 (9) | 0.0020 (8) | −0.0104 (9) |
C12 | 0.0207 (9) | 0.0244 (11) | 0.0257 (12) | −0.0053 (8) | −0.0019 (8) | −0.0085 (9) |
C13 | 0.0281 (10) | 0.0268 (12) | 0.0196 (11) | −0.0105 (9) | −0.0003 (8) | −0.0064 (9) |
C14 | 0.0325 (11) | 0.0265 (13) | 0.0302 (13) | −0.0064 (9) | 0.0002 (9) | −0.0072 (10) |
C15 | 0.0466 (13) | 0.0213 (12) | 0.0367 (14) | −0.0115 (10) | −0.0019 (10) | −0.0036 (10) |
C16 | 0.0468 (13) | 0.0354 (14) | 0.0331 (14) | −0.0249 (11) | 0.0010 (10) | −0.0027 (11) |
C17 | 0.0305 (11) | 0.0376 (14) | 0.0325 (13) | −0.0144 (10) | 0.0019 (9) | −0.0064 (11) |
C18 | 0.0290 (11) | 0.0247 (12) | 0.0282 (12) | −0.0075 (9) | −0.0010 (9) | −0.0051 (9) |
C19 | 0.0208 (10) | 0.0268 (12) | 0.0257 (12) | −0.0128 (9) | 0.0000 (8) | −0.0045 (9) |
C20 | 0.0261 (10) | 0.0292 (13) | 0.0314 (13) | −0.0080 (9) | −0.0063 (9) | −0.0045 (10) |
C21 | 0.0298 (12) | 0.0363 (14) | 0.0453 (16) | −0.0060 (10) | −0.0018 (10) | −0.0173 (12) |
C22 | 0.0374 (13) | 0.0480 (16) | 0.0337 (14) | −0.0202 (11) | 0.0059 (10) | −0.0199 (12) |
C23 | 0.0453 (13) | 0.0397 (14) | 0.0251 (13) | −0.0252 (11) | −0.0016 (10) | −0.0027 (10) |
C24 | 0.0335 (11) | 0.0244 (12) | 0.0288 (13) | −0.0137 (9) | −0.0030 (9) | −0.0009 (9) |
S—O2 | 1.4926 (15) | C12—C13 | 1.464 (3) |
S—C1 | 1.7690 (19) | C13—C14 | 1.388 (3) |
S—C19 | 1.801 (2) | C13—C18 | 1.402 (3) |
O1—C12 | 1.376 (2) | C14—C15 | 1.377 (3) |
O1—C11 | 1.380 (3) | C14—H14 | 0.9500 |
C1—C12 | 1.356 (3) | C15—C16 | 1.391 (3) |
C1—C2 | 1.455 (3) | C15—H15 | 0.9500 |
C2—C11 | 1.373 (3) | C16—C17 | 1.375 (3) |
C2—C3 | 1.426 (3) | C16—H16 | 0.9500 |
C3—C4 | 1.407 (3) | C17—C18 | 1.381 (3) |
C3—C8 | 1.431 (3) | C17—H17 | 0.9500 |
C4—C5 | 1.369 (3) | C18—H18 | 0.9500 |
C4—H4 | 0.9500 | C19—C24 | 1.380 (3) |
C5—C6 | 1.406 (3) | C19—C20 | 1.383 (3) |
C5—H5 | 0.9500 | C20—C21 | 1.381 (3) |
C6—C7 | 1.357 (4) | C20—H20 | 0.9500 |
C6—H6 | 0.9500 | C21—C22 | 1.389 (4) |
C7—C8 | 1.414 (3) | C21—H21 | 0.9500 |
C7—H7 | 0.9500 | C22—C23 | 1.382 (3) |
C8—C9 | 1.423 (3) | C22—H22 | 0.9500 |
C9—C10 | 1.355 (4) | C23—C24 | 1.386 (3) |
C9—H9 | 0.9500 | C23—H23 | 0.9500 |
C10—C11 | 1.406 (3) | C24—H24 | 0.9500 |
C10—H10 | 0.9500 | ||
O2—S—C1 | 110.64 (9) | C1—C12—C13 | 133.87 (18) |
O2—S—C19 | 106.60 (9) | O1—C12—C13 | 115.97 (18) |
C1—S—C19 | 98.59 (9) | C14—C13—C18 | 119.2 (2) |
C12—O1—C11 | 106.29 (16) | C14—C13—C12 | 120.17 (18) |
C12—C1—C2 | 107.88 (17) | C18—C13—C12 | 120.62 (19) |
C12—C1—S | 119.06 (15) | C15—C14—C13 | 120.8 (2) |
C2—C1—S | 132.80 (16) | C15—C14—H14 | 119.6 |
C11—C2—C3 | 119.15 (18) | C13—C14—H14 | 119.6 |
C11—C2—C1 | 104.07 (19) | C14—C15—C16 | 119.7 (2) |
C3—C2—C1 | 136.75 (18) | C14—C15—H15 | 120.2 |
C4—C3—C2 | 124.79 (18) | C16—C15—H15 | 120.2 |
C4—C3—C8 | 118.6 (2) | C17—C16—C15 | 119.9 (2) |
C2—C3—C8 | 116.6 (2) | C17—C16—H16 | 120.1 |
C5—C4—C3 | 120.9 (2) | C15—C16—H16 | 120.1 |
C5—C4—H4 | 119.5 | C16—C17—C18 | 121.0 (2) |
C3—C4—H4 | 119.5 | C16—C17—H17 | 119.5 |
C4—C5—C6 | 120.6 (2) | C18—C17—H17 | 119.5 |
C4—C5—H5 | 119.7 | C17—C18—C13 | 119.4 (2) |
C6—C5—H5 | 119.7 | C17—C18—H18 | 120.3 |
C7—C6—C5 | 119.8 (2) | C13—C18—H18 | 120.3 |
C7—C6—H6 | 120.1 | C24—C19—C20 | 121.2 (2) |
C5—C6—H6 | 120.1 | C24—C19—S | 118.22 (16) |
C6—C7—C8 | 121.5 (2) | C20—C19—S | 120.25 (17) |
C6—C7—H7 | 119.2 | C21—C20—C19 | 119.0 (2) |
C8—C7—H7 | 119.2 | C21—C20—H20 | 120.5 |
C7—C8—C9 | 121.0 (2) | C19—C20—H20 | 120.5 |
C7—C8—C3 | 118.5 (2) | C20—C21—C22 | 120.2 (2) |
C9—C8—C3 | 120.5 (2) | C20—C21—H21 | 119.9 |
C10—C9—C8 | 122.5 (2) | C22—C21—H21 | 119.9 |
C10—C9—H9 | 118.8 | C23—C22—C21 | 120.2 (2) |
C8—C9—H9 | 118.8 | C23—C22—H22 | 119.9 |
C9—C10—C11 | 116.1 (2) | C21—C22—H22 | 119.9 |
C9—C10—H10 | 122.0 | C22—C23—C24 | 119.8 (2) |
C11—C10—H10 | 122.0 | C22—C23—H23 | 120.1 |
C2—C11—O1 | 111.62 (17) | C24—C23—H23 | 120.1 |
C2—C11—C10 | 125.1 (2) | C19—C24—C23 | 119.5 (2) |
O1—C11—C10 | 123.3 (2) | C19—C24—H24 | 120.3 |
C1—C12—O1 | 110.10 (18) | C23—C24—H24 | 120.3 |
O2—S—C1—C12 | −136.67 (16) | C9—C10—C11—C2 | −0.1 (3) |
C19—S—C1—C12 | 111.89 (17) | C9—C10—C11—O1 | 179.1 (2) |
O2—S—C1—C2 | 50.0 (2) | C2—C1—C12—O1 | 1.4 (2) |
C19—S—C1—C2 | −61.5 (2) | S—C1—C12—O1 | −173.45 (13) |
C12—C1—C2—C11 | −0.5 (2) | C2—C1—C12—C13 | 178.2 (2) |
S—C1—C2—C11 | 173.40 (17) | S—C1—C12—C13 | 3.3 (3) |
C12—C1—C2—C3 | 177.6 (2) | C11—O1—C12—C1 | −1.8 (2) |
S—C1—C2—C3 | −8.5 (4) | C11—O1—C12—C13 | −179.21 (17) |
C11—C2—C3—C4 | 178.0 (2) | C1—C12—C13—C14 | −129.7 (3) |
C1—C2—C3—C4 | 0.1 (4) | O1—C12—C13—C14 | 47.0 (3) |
C11—C2—C3—C8 | −0.6 (3) | C1—C12—C13—C18 | 50.2 (3) |
C1—C2—C3—C8 | −178.5 (2) | O1—C12—C13—C18 | −133.2 (2) |
C2—C3—C4—C5 | −179.5 (2) | C18—C13—C14—C15 | −0.8 (3) |
C8—C3—C4—C5 | −0.9 (3) | C12—C13—C14—C15 | 179.1 (2) |
C3—C4—C5—C6 | 0.0 (3) | C13—C14—C15—C16 | 0.6 (4) |
C4—C5—C6—C7 | 0.9 (4) | C14—C15—C16—C17 | −0.1 (4) |
C5—C6—C7—C8 | −0.8 (4) | C15—C16—C17—C18 | −0.3 (4) |
C6—C7—C8—C9 | 178.5 (2) | C16—C17—C18—C13 | 0.1 (3) |
C6—C7—C8—C3 | −0.2 (3) | C14—C13—C18—C17 | 0.5 (3) |
C4—C3—C8—C7 | 1.1 (3) | C12—C13—C18—C17 | −179.4 (2) |
C2—C3—C8—C7 | 179.70 (19) | O2—S—C19—C24 | 16.08 (18) |
C4—C3—C8—C9 | −177.6 (2) | C1—S—C19—C24 | 130.73 (17) |
C2—C3—C8—C9 | 1.0 (3) | O2—S—C19—C20 | −170.04 (16) |
C7—C8—C9—C10 | −179.7 (2) | C1—S—C19—C20 | −55.39 (18) |
C3—C8—C9—C10 | −1.1 (3) | C24—C19—C20—C21 | −1.9 (3) |
C8—C9—C10—C11 | 0.6 (3) | S—C19—C20—C21 | −175.57 (17) |
C3—C2—C11—O1 | −179.15 (17) | C19—C20—C21—C22 | 0.6 (3) |
C1—C2—C11—O1 | −0.6 (2) | C20—C21—C22—C23 | 0.6 (4) |
C3—C2—C11—C10 | 0.1 (3) | C21—C22—C23—C24 | −0.5 (3) |
C1—C2—C11—C10 | 178.7 (2) | C20—C19—C24—C23 | 2.0 (3) |
C12—O1—C11—C2 | 1.5 (2) | S—C19—C24—C23 | 175.80 (15) |
C12—O1—C11—C10 | −177.8 (2) | C22—C23—C24—C19 | −0.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O2i | 0.95 | 2.59 | 3.488 (3) | 158 |
C18—H18···O2ii | 0.95 | 2.57 | 3.323 (3) | 137 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C24H16O2S |
Mr | 368.43 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 9.2262 (7), 10.3430 (8), 10.4296 (8) |
α, β, γ (°) | 78.298 (1), 86.849 (1), 67.506 (1) |
V (Å3) | 900.15 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6736, 3140, 2602 |
Rint | 0.076 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.106, 1.06 |
No. of reflections | 3140 |
No. of parameters | 244 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.36 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O2i | 0.95 | 2.59 | 3.488 (3) | 158.0 |
C18—H18···O2ii | 0.95 | 2.57 | 3.323 (3) | 136.7 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+1. |
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The naphthofuran ring system has attracted widespread interest in view of their biological and pharmacological activities (Goel & Dixit, 2004; Hagiwara et al., 1999; Piloto et al., 2005). This work is related to our communications on the synthesis and structures of naphtho[2,1-b]furan analogues, viz. 2-methyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Choi et al., 2007) and 2-methyl-1-(phenylsulfonyl)naphtho[2,1-b]furan (Choi et al., 2008). We present the crystal structure of the title compound (I), 2-phenyl-1-(phenylsulfinyl)naphtho[2,1-b]furan (Fig. 1).
The naphthofuran unit is essentially planar, with a mean deviation of 0.015 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle in (I) formed by the plane of the naphthofuran ring and the plane of 2-phenyl ring is 48.21 (6)°, and the phenyl ring (C19-C24) with 82.34 (5)° lies toward the naphthofuran plane. The crystal packing (Fig. 2) is stabilized by aromatic π–π interactions between the central benzene rings from the adjacent molecules. The Cg···Cgiii distance is 3.516 (3) Å (Cg is the centroide of the C2/C3/C8/C9/C10/C11 benzene ring, symmetry code as in Fig. 2). The molecular packing is further stabilized by weak non-classical intermolecular C–H···O hydrogen bonds, the first between an aromatic H atom of the naphthofuran fragment and the S═O unit, the second between an aromatic H atom of 2-phenyl ring and the S═O unit, respectively (Table 1 and Fig. 2; symmetry code as in Fig. 2).