organic compounds
2-Methyl-1-(4-methylphenylsulfinyl)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, C20H16O2S, the 4-methylphenyl ring makes a dihedral angle of 82.60 (4)° with the mean plane [r.m.s. deviation = 0.007 (1) Å] of the naphthofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds, and by a slipped π–π interaction between the central naphthofuran benzene rings of neighbouring molecules [centroid-to-centroid distance = 3.671 (2) Å, interplanar distance = 3.349 (2) Å and slippage = 1.503 (2)°].
Related literature
For the pharmacological activity of naphthofuran compounds, see: Goel & Dixit (2004); Hagiwara et al. (1999); Piloto et al. (2005). For the crystal structures of related compounds, see: Choi et al. (2007, 2008).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell 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.
Supporting information
10.1107/S1600536812003121/lr2049sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812003121/lr2049Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812003121/lr2049Isup3.cml
77% 3-Chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 2-methyl-1-(4-methylphenylsulfanyl) naphtho[2,1-b]furan (334 mg, 1.1 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 5 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by
(hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 433–448 K; Rf = 0.51 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C)for methyl H atoms.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).C20H16O2S | F(000) = 672 |
Mr = 320.39 | Dx = 1.361 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5690 reflections |
a = 6.5052 (1) Å | θ = 2.8–28.1° |
b = 16.7418 (3) Å | µ = 0.21 mm−1 |
c = 14.4935 (2) Å | T = 173 K |
β = 97.883 (1)° | Block, colourless |
V = 1563.55 (4) Å3 | 0.28 × 0.28 × 0.26 mm |
Z = 4 |
Bruker SMART APEXII CCD diffractometer | 3896 independent reflections |
Radiation source: rotating anode | 3271 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.028 |
Detector resolution: 10.0 pixels mm-1 | θmax = 28.3°, θmin = 1.9° |
ϕ and ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −19→22 |
Tmin = 0.677, Tmax = 0.746 | l = −19→19 |
15390 measured 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)] = 0.039 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0548P)2 + 0.534P] where P = (Fo2 + 2Fc2)/3 |
3896 reflections | (Δ/σ)max < 0.001 |
210 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C20H16O2S | V = 1563.55 (4) Å3 |
Mr = 320.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.5052 (1) Å | µ = 0.21 mm−1 |
b = 16.7418 (3) Å | T = 173 K |
c = 14.4935 (2) Å | 0.28 × 0.28 × 0.26 mm |
β = 97.883 (1)° |
Bruker SMART APEXII CCD diffractometer | 3896 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3271 reflections with I > 2σ(I) |
Tmin = 0.677, Tmax = 0.746 | Rint = 0.028 |
15390 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.29 e Å−3 |
3896 reflections | Δρmin = −0.39 e Å−3 |
210 parameters |
Geometry. Cg···Cgiv distance = 3.671 (2) Å; (iv) -x + 1, -y + 1, -z Cg is the centroid of the C2/C3/C8–C11 benzene ring. |
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 | ||
S1 | 0.54869 (6) | 0.29240 (2) | 0.22725 (3) | 0.02964 (11) | |
O1 | 0.18369 (15) | 0.42901 (7) | 0.06023 (7) | 0.0332 (2) | |
O2 | 0.77697 (17) | 0.28641 (6) | 0.22477 (8) | 0.0391 (3) | |
C1 | 0.4389 (2) | 0.37111 (8) | 0.15685 (9) | 0.0268 (3) | |
C2 | 0.4942 (2) | 0.45457 (8) | 0.14760 (9) | 0.0251 (3) | |
C3 | 0.6672 (2) | 0.50427 (8) | 0.17904 (9) | 0.0253 (3) | |
C4 | 0.8502 (2) | 0.47737 (9) | 0.23408 (10) | 0.0301 (3) | |
H4 | 0.8619 | 0.4230 | 0.2528 | 0.036* | |
C5 | 1.0110 (2) | 0.52903 (9) | 0.26072 (12) | 0.0368 (3) | |
H5 | 1.1337 | 0.5100 | 0.2972 | 0.044* | |
C6 | 0.9958 (2) | 0.60987 (9) | 0.23450 (12) | 0.0375 (4) | |
H6 | 1.1067 | 0.6455 | 0.2544 | 0.045* | |
C7 | 0.8224 (2) | 0.63704 (9) | 0.18063 (11) | 0.0339 (3) | |
H7 | 0.8146 | 0.6917 | 0.1629 | 0.041* | |
C8 | 0.6534 (2) | 0.58600 (8) | 0.15034 (10) | 0.0282 (3) | |
C9 | 0.4756 (2) | 0.61434 (9) | 0.09111 (10) | 0.0338 (3) | |
H9 | 0.4694 | 0.6691 | 0.0736 | 0.041* | |
C10 | 0.3145 (2) | 0.56566 (10) | 0.05886 (10) | 0.0346 (3) | |
H10 | 0.1974 | 0.5847 | 0.0185 | 0.042* | |
C11 | 0.3302 (2) | 0.48621 (9) | 0.08821 (10) | 0.0289 (3) | |
C12 | 0.2541 (2) | 0.35928 (9) | 0.10221 (10) | 0.0309 (3) | |
C13 | 0.1180 (3) | 0.28882 (10) | 0.08024 (12) | 0.0399 (4) | |
H13A | 0.1879 | 0.2409 | 0.1079 | 0.060* | |
H13B | 0.0887 | 0.2822 | 0.0125 | 0.060* | |
H13C | −0.0124 | 0.2967 | 0.1058 | 0.060* | |
C14 | 0.5188 (2) | 0.33407 (8) | 0.33886 (9) | 0.0254 (3) | |
C15 | 0.6874 (2) | 0.33510 (9) | 0.40837 (11) | 0.0330 (3) | |
H15 | 0.8197 | 0.3177 | 0.3958 | 0.040* | |
C16 | 0.6611 (2) | 0.36179 (10) | 0.49654 (11) | 0.0367 (3) | |
H16 | 0.7769 | 0.3626 | 0.5442 | 0.044* | |
C17 | 0.4692 (2) | 0.38742 (9) | 0.51671 (10) | 0.0318 (3) | |
C18 | 0.3013 (2) | 0.38436 (9) | 0.44579 (10) | 0.0316 (3) | |
H18 | 0.1685 | 0.4011 | 0.4585 | 0.038* | |
C19 | 0.3236 (2) | 0.35751 (8) | 0.35733 (10) | 0.0289 (3) | |
H19 | 0.2072 | 0.3551 | 0.3100 | 0.035* | |
C20 | 0.4422 (3) | 0.41837 (11) | 0.61182 (11) | 0.0416 (4) | |
H20A | 0.5394 | 0.3909 | 0.6590 | 0.062* | |
H20B | 0.2997 | 0.4084 | 0.6236 | 0.062* | |
H20C | 0.4700 | 0.4759 | 0.6147 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0360 (2) | 0.02007 (18) | 0.0343 (2) | 0.00179 (13) | 0.00981 (14) | −0.00098 (13) |
O1 | 0.0290 (5) | 0.0398 (6) | 0.0299 (5) | 0.0007 (4) | 0.0012 (4) | −0.0028 (4) |
O2 | 0.0378 (6) | 0.0329 (6) | 0.0494 (7) | 0.0121 (5) | 0.0161 (5) | 0.0032 (5) |
C1 | 0.0293 (7) | 0.0260 (7) | 0.0259 (7) | −0.0002 (5) | 0.0068 (5) | −0.0021 (5) |
C2 | 0.0282 (6) | 0.0246 (7) | 0.0232 (6) | 0.0036 (5) | 0.0066 (5) | −0.0009 (5) |
C3 | 0.0295 (7) | 0.0231 (7) | 0.0245 (6) | 0.0023 (5) | 0.0079 (5) | −0.0015 (5) |
C4 | 0.0299 (7) | 0.0235 (7) | 0.0372 (8) | 0.0009 (5) | 0.0058 (6) | 0.0014 (6) |
C5 | 0.0304 (7) | 0.0335 (8) | 0.0458 (9) | −0.0007 (6) | 0.0027 (6) | 0.0006 (7) |
C6 | 0.0354 (8) | 0.0310 (8) | 0.0475 (9) | −0.0082 (6) | 0.0110 (7) | −0.0053 (7) |
C7 | 0.0440 (8) | 0.0223 (7) | 0.0384 (8) | −0.0018 (6) | 0.0158 (7) | −0.0008 (6) |
C8 | 0.0362 (7) | 0.0237 (7) | 0.0265 (7) | 0.0023 (5) | 0.0114 (6) | −0.0009 (5) |
C9 | 0.0449 (8) | 0.0266 (7) | 0.0312 (7) | 0.0101 (6) | 0.0101 (6) | 0.0046 (6) |
C10 | 0.0372 (8) | 0.0365 (8) | 0.0295 (7) | 0.0117 (6) | 0.0023 (6) | 0.0039 (6) |
C11 | 0.0285 (7) | 0.0326 (7) | 0.0259 (7) | 0.0027 (6) | 0.0049 (5) | −0.0023 (6) |
C12 | 0.0322 (7) | 0.0336 (8) | 0.0281 (7) | −0.0011 (6) | 0.0086 (6) | −0.0044 (6) |
C13 | 0.0371 (8) | 0.0427 (9) | 0.0402 (9) | −0.0106 (7) | 0.0061 (7) | −0.0088 (7) |
C14 | 0.0293 (7) | 0.0188 (6) | 0.0285 (7) | 0.0001 (5) | 0.0054 (5) | 0.0029 (5) |
C15 | 0.0266 (7) | 0.0340 (8) | 0.0383 (8) | 0.0012 (6) | 0.0041 (6) | 0.0032 (6) |
C16 | 0.0325 (7) | 0.0423 (9) | 0.0338 (8) | −0.0025 (6) | −0.0016 (6) | 0.0031 (7) |
C17 | 0.0374 (8) | 0.0288 (7) | 0.0299 (7) | −0.0075 (6) | 0.0070 (6) | 0.0017 (6) |
C18 | 0.0291 (7) | 0.0315 (8) | 0.0354 (8) | 0.0003 (6) | 0.0090 (6) | 0.0010 (6) |
C19 | 0.0267 (7) | 0.0285 (7) | 0.0311 (7) | 0.0007 (5) | 0.0029 (5) | 0.0020 (6) |
C20 | 0.0502 (9) | 0.0444 (9) | 0.0318 (8) | −0.0107 (8) | 0.0111 (7) | −0.0035 (7) |
S1—O2 | 1.4938 (11) | C9—H9 | 0.9500 |
S1—C1 | 1.7573 (15) | C10—C11 | 1.396 (2) |
S1—C14 | 1.7964 (14) | C10—H10 | 0.9500 |
O1—C12 | 1.3662 (18) | C12—C13 | 1.483 (2) |
O1—C11 | 1.3727 (17) | C13—H13A | 0.9800 |
C1—C12 | 1.360 (2) | C13—H13B | 0.9800 |
C1—C2 | 1.4537 (19) | C13—H13C | 0.9800 |
C2—C11 | 1.3813 (19) | C14—C15 | 1.384 (2) |
C2—C3 | 1.4232 (19) | C14—C19 | 1.3901 (18) |
C3—C4 | 1.413 (2) | C15—C16 | 1.386 (2) |
C3—C8 | 1.4293 (19) | C15—H15 | 0.9500 |
C4—C5 | 1.371 (2) | C16—C17 | 1.389 (2) |
C4—H4 | 0.9500 | C16—H16 | 0.9500 |
C5—C6 | 1.406 (2) | C17—C18 | 1.394 (2) |
C5—H5 | 0.9500 | C17—C20 | 1.505 (2) |
C6—C7 | 1.359 (2) | C18—C19 | 1.385 (2) |
C6—H6 | 0.9500 | C18—H18 | 0.9500 |
C7—C8 | 1.414 (2) | C19—H19 | 0.9500 |
C7—H7 | 0.9500 | C20—H20A | 0.9800 |
C8—C9 | 1.424 (2) | C20—H20B | 0.9800 |
C9—C10 | 1.359 (2) | C20—H20C | 0.9800 |
O2—S1—C1 | 111.27 (6) | O1—C11—C10 | 123.78 (13) |
O2—S1—C14 | 106.16 (7) | C2—C11—C10 | 124.97 (14) |
C1—S1—C14 | 98.40 (6) | C1—C12—O1 | 110.52 (13) |
C12—O1—C11 | 106.72 (11) | C1—C12—C13 | 134.00 (15) |
C12—C1—C2 | 107.26 (13) | O1—C12—C13 | 115.48 (13) |
C12—C1—S1 | 119.03 (11) | C12—C13—H13A | 109.5 |
C2—C1—S1 | 133.49 (11) | C12—C13—H13B | 109.5 |
C11—C2—C3 | 118.98 (13) | H13A—C13—H13B | 109.5 |
C11—C2—C1 | 104.24 (12) | C12—C13—H13C | 109.5 |
C3—C2—C1 | 136.67 (13) | H13A—C13—H13C | 109.5 |
C4—C3—C2 | 124.22 (13) | H13B—C13—H13C | 109.5 |
C4—C3—C8 | 118.95 (13) | C15—C14—C19 | 120.66 (13) |
C2—C3—C8 | 116.82 (13) | C15—C14—S1 | 119.20 (10) |
C5—C4—C3 | 120.60 (14) | C19—C14—S1 | 119.84 (11) |
C5—C4—H4 | 119.7 | C14—C15—C16 | 119.32 (13) |
C3—C4—H4 | 119.7 | C14—C15—H15 | 120.3 |
C4—C5—C6 | 120.57 (15) | C16—C15—H15 | 120.3 |
C4—C5—H5 | 119.7 | C15—C16—C17 | 121.45 (14) |
C6—C5—H5 | 119.7 | C15—C16—H16 | 119.3 |
C7—C6—C5 | 119.97 (14) | C17—C16—H16 | 119.3 |
C7—C6—H6 | 120.0 | C16—C17—C18 | 117.99 (14) |
C5—C6—H6 | 120.0 | C16—C17—C20 | 121.35 (14) |
C6—C7—C8 | 121.65 (14) | C18—C17—C20 | 120.66 (14) |
C6—C7—H7 | 119.2 | C19—C18—C17 | 121.58 (13) |
C8—C7—H7 | 119.2 | C19—C18—H18 | 119.2 |
C7—C8—C9 | 121.24 (13) | C17—C18—H18 | 119.2 |
C7—C8—C3 | 118.23 (13) | C18—C19—C14 | 118.97 (13) |
C9—C8—C3 | 120.51 (13) | C18—C19—H19 | 120.5 |
C10—C9—C8 | 122.13 (14) | C14—C19—H19 | 120.5 |
C10—C9—H9 | 118.9 | C17—C20—H20A | 109.5 |
C8—C9—H9 | 118.9 | C17—C20—H20B | 109.5 |
C9—C10—C11 | 116.49 (14) | H20A—C20—H20B | 109.5 |
C9—C10—H10 | 121.8 | C17—C20—H20C | 109.5 |
C11—C10—H10 | 121.8 | H20A—C20—H20C | 109.5 |
O1—C11—C2 | 111.24 (12) | H20B—C20—H20C | 109.5 |
O2—S1—C1—C12 | 137.65 (11) | C12—O1—C11—C10 | 179.24 (13) |
C14—S1—C1—C12 | −111.29 (12) | C3—C2—C11—O1 | 176.11 (11) |
O2—S1—C1—C2 | −48.61 (15) | C1—C2—C11—O1 | −0.85 (14) |
C14—S1—C1—C2 | 62.45 (14) | C3—C2—C11—C10 | −3.1 (2) |
C12—C1—C2—C11 | 1.38 (14) | C1—C2—C11—C10 | 179.93 (13) |
S1—C1—C2—C11 | −172.89 (11) | C9—C10—C11—O1 | −178.33 (13) |
C12—C1—C2—C3 | −174.74 (15) | C9—C10—C11—C2 | 0.8 (2) |
S1—C1—C2—C3 | 11.0 (2) | C2—C1—C12—O1 | −1.46 (15) |
C11—C2—C3—C4 | −175.09 (12) | S1—C1—C12—O1 | 173.79 (9) |
C1—C2—C3—C4 | 0.6 (2) | C2—C1—C12—C13 | 179.00 (15) |
C11—C2—C3—C8 | 3.32 (18) | S1—C1—C12—C13 | −5.8 (2) |
C1—C2—C3—C8 | 179.02 (14) | C11—O1—C12—C1 | 0.93 (15) |
C2—C3—C4—C5 | 179.31 (13) | C11—O1—C12—C13 | −179.43 (12) |
C8—C3—C4—C5 | 0.9 (2) | O2—S1—C14—C15 | −15.36 (13) |
C3—C4—C5—C6 | 0.6 (2) | C1—S1—C14—C15 | −130.48 (12) |
C4—C5—C6—C7 | −1.4 (2) | O2—S1—C14—C19 | 170.95 (11) |
C5—C6—C7—C8 | 0.6 (2) | C1—S1—C14—C19 | 55.83 (12) |
C6—C7—C8—C9 | −177.67 (14) | C19—C14—C15—C16 | −1.7 (2) |
C6—C7—C8—C3 | 1.0 (2) | S1—C14—C15—C16 | −175.29 (12) |
C4—C3—C8—C7 | −1.69 (19) | C14—C15—C16—C17 | 0.1 (2) |
C2—C3—C8—C7 | 179.81 (12) | C15—C16—C17—C18 | 1.0 (2) |
C4—C3—C8—C9 | 176.95 (12) | C15—C16—C17—C20 | −178.40 (15) |
C2—C3—C8—C9 | −1.56 (18) | C16—C17—C18—C19 | −0.7 (2) |
C7—C8—C9—C10 | 177.87 (14) | C20—C17—C18—C19 | 178.78 (14) |
C3—C8—C9—C10 | −0.7 (2) | C17—C18—C19—C14 | −0.8 (2) |
C8—C9—C10—C11 | 1.2 (2) | C15—C14—C19—C18 | 2.0 (2) |
C12—O1—C11—C2 | 0.01 (15) | S1—C14—C19—C18 | 175.61 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.95 | 2.48 | 3.3211 (19) | 147 |
C10—H10···O1ii | 0.95 | 2.59 | 3.4579 (19) | 152 |
C13—H13C···O2iii | 0.98 | 2.35 | 3.2538 (19) | 153 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x, −y+1, −z; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C20H16O2S |
Mr | 320.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 6.5052 (1), 16.7418 (3), 14.4935 (2) |
β (°) | 97.883 (1) |
V (Å3) | 1563.55 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.28 × 0.28 × 0.26 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.677, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15390, 3896, 3271 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.107, 1.03 |
No. of reflections | 3896 |
No. of parameters | 210 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.39 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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 |
C6—H6···O2i | 0.95 | 2.48 | 3.3211 (19) | 147.1 |
C10—H10···O1ii | 0.95 | 2.59 | 3.4579 (19) | 151.5 |
C13—H13C···O2iii | 0.98 | 2.35 | 3.2538 (19) | 152.7 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x, −y+1, −z; (iii) x−1, y, z. |
Acknowledgements
This work was supported by the Blue-Bio Industry Regional Innovation Centre (grant No. RIC08-06-07) at Dongeui University as an RIC programme under the Ministry of Knowledge Economy and Busan city.
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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.
Naphthofuran analogues have drawn much attention owing to their valuable biological activities (Goel & Dixit, 2004; Hagiwara et al., 1999; Piloto et al., 2005). As a part of our continuing study of 2-methylnaphthofuran derivatives containing either 1-phenylsulfinyl (Choi et al., 2007) or 1-phenylsulfonyl (Choi et al., 2008) substituents, we report herein the crystal structure of the title compound.
In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle between the 4-methylphenyl ring and the mean plane of the naphthofuran fragment is 82.60 (4)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 2) is further stabilized by a weak slipped π–π interaction between adjacent central benzene rings of the naphthofuran moiety, with a Cg···Cgiv distance of 3.671 (2) Å, and an interplanar distance of 3.349 (2) Å, resulting in a slippage of 1.503 (2) Å, Cg is the centroid of the C2,C3,C8,C9,C10,C11 benzene ring and (iv) is the -x + 1, -y + 1, -z symmetry code.