organic compounds
3-(4-Chlorophenylsulfonyl)-2-methylnaphtho[1,2-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
The title compound, C19H13ClO3S, was prepared by the oxidation of 3-(4-chlorophenylsulfanyl)-2-methylnaphtho[1,2-b]furan with 3-chloroperoxybenzoic acid. The 4-chlorophenyl ring makes a dihedral angle of 68.59 (5)° with the plane of the naphthofuran fragment. The is stabilized by π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.635 (3) Å], and by C—H⋯π interactions between a methyl H atom and the furan ring of an adjacent molecule. In addition, the exhibits intermolecular C—H⋯O interactions.
Related literature
For the crystal structures of similar 2-methylnaphtho[1,2-b]furan derivatives, see: Choi et al. (2006, 2008).
Experimental
Crystal data
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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/S1600536808009215/at2553sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009215/at2553Isup2.hkl
3-Chloroperoxybenzoic acid (77%, 336 mg, 1.5 mmol) was added in small portions to a stirred solution of 3-(4-chlorophenylsulfanyl)-2-methylnaphtho[1,2-b]furan (227 mg, 0.7 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 4 h, 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 δ 2.91 (s, 3H), 7.45-7.64 (m, 4H), 7.75 (d, J = 8.44 Hz, 1H), 7.90-8.02 (m, 4H), 8.21 (d, J = 8.04 Hz, 1H); EI-MS 358 [M+2], 356 [M+].
(hexane-ethyl acetate, 2 : 1 v/v) to afford the title compound as a colourless solid [yield 82 %, m.p. 427-428 K; Rf = 0.69 (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 acetone at room temperature. Spectroscopic analysis: 1H NMR (CDCl3, 400 MHz)All H atoms were geometrically positioned and refined using a riding model, with C—H = 0.95 Å for aromatic H atoms and 0.98 Å for methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for aromatic and Uiso(H) = 1.5Ueq(C) for methyl 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).C19H13ClO3S | Dx = 1.449 Mg m−3 |
Mr = 356.80 | Melting point = 427–428 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 7325 reflections |
a = 8.1155 (3) Å | θ = 2.2–28.2° |
b = 18.6014 (7) Å | µ = 0.38 mm−1 |
c = 10.8319 (4) Å | T = 173 K |
V = 1635.18 (11) Å3 | Block, colourless |
Z = 4 | 0.60 × 0.40 × 0.40 mm |
F(000) = 736 |
Bruker SMART CCD diffractometer | 2611 independent reflections |
Radiation source: fine-focus sealed tube | 2532 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.0°, θmin = 2.7° |
ϕ and ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | k = −23→23 |
Tmin = 0.842, Tmax = 0.857 | l = −6→13 |
9543 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.066 | w = 1/[σ2(Fo2) + (0.0417P)2 + 0.2762P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2611 reflections | Δρmax = 0.26 e Å−3 |
218 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 728 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (5) |
C19H13ClO3S | V = 1635.18 (11) Å3 |
Mr = 356.80 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 8.1155 (3) Å | µ = 0.38 mm−1 |
b = 18.6014 (7) Å | T = 173 K |
c = 10.8319 (4) Å | 0.60 × 0.40 × 0.40 mm |
Bruker SMART CCD diffractometer | 2611 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | 2532 reflections with I > 2σ(I) |
Tmin = 0.842, Tmax = 0.857 | Rint = 0.016 |
9543 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.066 | Δρmax = 0.26 e Å−3 |
S = 1.06 | Δρmin = −0.20 e Å−3 |
2611 reflections | Absolute structure: Flack (1983), 728 Freidel pairs |
218 parameters | Absolute structure parameter: −0.01 (5) |
1 restraint |
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 | ||
Cl | −0.09521 (6) | −0.07862 (3) | 0.70659 (5) | 0.04239 (14) | |
S | 0.49747 (5) | 0.08522 (2) | 0.47158 (5) | 0.02560 (10) | |
O1 | 0.55982 (14) | 0.27683 (6) | 0.61467 (14) | 0.0294 (3) | |
O2 | 0.64177 (14) | 0.04043 (6) | 0.48194 (16) | 0.0336 (3) | |
O3 | 0.44235 (16) | 0.10742 (7) | 0.35113 (14) | 0.0344 (3) | |
C1 | 0.5352 (2) | 0.16153 (8) | 0.55974 (18) | 0.0247 (3) | |
C2 | 0.62790 (19) | 0.16344 (9) | 0.67380 (18) | 0.0256 (4) | |
C3 | 0.7034 (2) | 0.11205 (9) | 0.75222 (19) | 0.0292 (4) | |
H3 | 0.6974 | 0.0621 | 0.7341 | 0.035* | |
C4 | 0.7847 (2) | 0.13619 (9) | 0.85426 (19) | 0.0305 (4) | |
H4 | 0.8359 | 0.1022 | 0.9073 | 0.037* | |
C5 | 0.7955 (2) | 0.21145 (10) | 0.88442 (19) | 0.0302 (4) | |
C6 | 0.8787 (2) | 0.23535 (11) | 0.9915 (2) | 0.0386 (5) | |
H6 | 0.9282 | 0.2014 | 1.0456 | 0.046* | |
C7 | 0.8882 (3) | 0.30743 (12) | 1.0175 (2) | 0.0449 (5) | |
H7 | 0.9442 | 0.3229 | 1.0898 | 0.054* | |
C8 | 0.8164 (3) | 0.35875 (11) | 0.9391 (2) | 0.0421 (5) | |
H8 | 0.8249 | 0.4084 | 0.9585 | 0.051* | |
C9 | 0.7342 (2) | 0.33765 (9) | 0.8346 (2) | 0.0347 (4) | |
H9 | 0.6858 | 0.3725 | 0.7817 | 0.042* | |
C10 | 0.7220 (2) | 0.26328 (9) | 0.80628 (19) | 0.0280 (4) | |
C11 | 0.63904 (19) | 0.23541 (8) | 0.7025 (2) | 0.0261 (3) | |
C12 | 0.4971 (2) | 0.23071 (9) | 0.5286 (2) | 0.0280 (4) | |
C13 | 0.3328 (2) | 0.03991 (8) | 0.54446 (17) | 0.0244 (3) | |
C14 | 0.3626 (2) | −0.01619 (9) | 0.6257 (2) | 0.0309 (4) | |
H14 | 0.4725 | −0.0296 | 0.6455 | 0.037* | |
C15 | 0.2315 (2) | −0.05239 (10) | 0.6775 (2) | 0.0347 (4) | |
H15 | 0.2495 | −0.0909 | 0.7335 | 0.042* | |
C16 | 0.0717 (2) | −0.03142 (10) | 0.64619 (18) | 0.0287 (4) | |
C17 | 0.0409 (2) | 0.02495 (10) | 0.5670 (2) | 0.0297 (4) | |
H17 | −0.0691 | 0.0385 | 0.5479 | 0.036* | |
C18 | 0.1726 (2) | 0.06139 (9) | 0.51591 (18) | 0.0268 (4) | |
H18 | 0.1543 | 0.1008 | 0.4618 | 0.032* | |
C19 | 0.4122 (2) | 0.26521 (10) | 0.4225 (2) | 0.0354 (4) | |
H19A | 0.3484 | 0.3065 | 0.4519 | 0.053* | |
H19B | 0.3379 | 0.2304 | 0.3835 | 0.053* | |
H19C | 0.4941 | 0.2814 | 0.3622 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0366 (2) | 0.0513 (3) | 0.0393 (3) | −0.01236 (19) | 0.0047 (2) | 0.0104 (2) |
S | 0.02092 (18) | 0.02869 (18) | 0.0272 (2) | −0.00070 (14) | 0.00189 (17) | −0.0036 (2) |
O1 | 0.0279 (6) | 0.0247 (5) | 0.0357 (7) | −0.0001 (5) | 0.0022 (6) | 0.0033 (6) |
O2 | 0.0221 (5) | 0.0340 (6) | 0.0447 (9) | 0.0030 (5) | 0.0019 (6) | −0.0096 (7) |
O3 | 0.0317 (6) | 0.0431 (7) | 0.0285 (7) | −0.0038 (6) | 0.0033 (6) | 0.0006 (6) |
C1 | 0.0212 (7) | 0.0245 (7) | 0.0284 (9) | −0.0012 (6) | 0.0030 (7) | −0.0019 (7) |
C2 | 0.0209 (7) | 0.0273 (7) | 0.0286 (10) | −0.0015 (6) | 0.0043 (7) | −0.0023 (7) |
C3 | 0.0298 (8) | 0.0244 (8) | 0.0335 (10) | 0.0010 (6) | 0.0024 (8) | 0.0002 (7) |
C4 | 0.0305 (8) | 0.0300 (8) | 0.0310 (10) | 0.0027 (7) | 0.0008 (8) | 0.0011 (8) |
C5 | 0.0246 (8) | 0.0346 (9) | 0.0314 (10) | −0.0023 (6) | 0.0044 (8) | −0.0044 (8) |
C6 | 0.0346 (9) | 0.0471 (11) | 0.0339 (12) | −0.0016 (8) | 0.0003 (9) | −0.0045 (9) |
C7 | 0.0432 (11) | 0.0516 (11) | 0.0401 (13) | −0.0097 (9) | −0.0022 (10) | −0.0154 (11) |
C8 | 0.0436 (11) | 0.0349 (9) | 0.0478 (14) | −0.0115 (8) | 0.0076 (10) | −0.0133 (9) |
C9 | 0.0347 (9) | 0.0287 (8) | 0.0406 (11) | −0.0054 (7) | 0.0085 (9) | −0.0035 (8) |
C10 | 0.0243 (7) | 0.0272 (8) | 0.0326 (10) | −0.0025 (6) | 0.0054 (8) | −0.0048 (7) |
C11 | 0.0219 (7) | 0.0250 (7) | 0.0315 (9) | −0.0004 (6) | 0.0052 (8) | 0.0016 (8) |
C12 | 0.0208 (7) | 0.0301 (8) | 0.0330 (10) | −0.0023 (6) | 0.0029 (7) | 0.0009 (8) |
C13 | 0.0227 (7) | 0.0257 (7) | 0.0247 (9) | −0.0012 (6) | 0.0003 (7) | −0.0036 (7) |
C14 | 0.0272 (8) | 0.0316 (8) | 0.0338 (10) | 0.0005 (7) | −0.0081 (8) | 0.0026 (8) |
C15 | 0.0373 (9) | 0.0339 (9) | 0.0330 (11) | −0.0025 (7) | −0.0074 (8) | 0.0083 (8) |
C16 | 0.0281 (8) | 0.0336 (8) | 0.0244 (10) | −0.0071 (7) | 0.0010 (8) | −0.0012 (7) |
C17 | 0.0235 (8) | 0.0358 (9) | 0.0299 (10) | 0.0016 (6) | 0.0007 (8) | −0.0011 (8) |
C18 | 0.0268 (8) | 0.0277 (7) | 0.0261 (9) | 0.0036 (6) | −0.0008 (7) | 0.0001 (7) |
C19 | 0.0321 (9) | 0.0337 (9) | 0.0403 (12) | 0.0032 (7) | −0.0025 (9) | 0.0059 (8) |
Cl—C16 | 1.7416 (17) | C7—H7 | 0.9500 |
S—O3 | 1.4397 (16) | C8—C9 | 1.371 (3) |
S—O2 | 1.4416 (12) | C8—H8 | 0.9500 |
S—C1 | 1.7379 (17) | C9—C10 | 1.421 (2) |
S—C13 | 1.7663 (17) | C9—H9 | 0.9500 |
O1—C12 | 1.365 (2) | C10—C11 | 1.409 (3) |
O1—C11 | 1.383 (2) | C12—C19 | 1.485 (3) |
C1—C12 | 1.366 (2) | C13—C14 | 1.386 (3) |
C1—C2 | 1.447 (3) | C13—C18 | 1.394 (2) |
C2—C11 | 1.377 (2) | C14—C15 | 1.379 (3) |
C2—C3 | 1.418 (3) | C14—H14 | 0.9500 |
C3—C4 | 1.363 (3) | C15—C16 | 1.396 (3) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C4—C5 | 1.440 (2) | C16—C17 | 1.378 (3) |
C4—H4 | 0.9500 | C17—C18 | 1.382 (3) |
C5—C6 | 1.414 (3) | C17—H17 | 0.9500 |
C5—C10 | 1.415 (3) | C18—H18 | 0.9500 |
C6—C7 | 1.372 (3) | C19—H19A | 0.9800 |
C6—H6 | 0.9500 | C19—H19B | 0.9800 |
C7—C8 | 1.404 (3) | C19—H19C | 0.9800 |
O3—S—O2 | 119.25 (10) | C11—C10—C5 | 115.35 (15) |
O3—S—C1 | 108.57 (8) | C11—C10—C9 | 124.35 (18) |
O2—S—C1 | 106.63 (8) | C5—C10—C9 | 120.30 (18) |
O3—S—C13 | 107.87 (8) | C2—C11—O1 | 110.85 (17) |
O2—S—C13 | 107.70 (8) | C2—C11—C10 | 124.68 (17) |
C1—S—C13 | 106.11 (8) | O1—C11—C10 | 124.47 (14) |
C12—O1—C11 | 107.04 (13) | O1—C12—C1 | 109.81 (17) |
C12—C1—C2 | 107.78 (16) | O1—C12—C19 | 115.45 (14) |
C12—C1—S | 126.43 (15) | C1—C12—C19 | 134.68 (18) |
C2—C1—S | 125.51 (13) | C14—C13—C18 | 121.29 (16) |
C11—C2—C3 | 119.46 (17) | C14—C13—S | 120.70 (13) |
C11—C2—C1 | 104.52 (15) | C18—C13—S | 117.99 (13) |
C3—C2—C1 | 136.01 (16) | C15—C14—C13 | 119.40 (16) |
C4—C3—C2 | 118.21 (16) | C15—C14—H14 | 120.3 |
C4—C3—H3 | 120.9 | C13—C14—H14 | 120.3 |
C2—C3—H3 | 120.9 | C14—C15—C16 | 118.81 (17) |
C3—C4—C5 | 122.26 (18) | C14—C15—H15 | 120.6 |
C3—C4—H4 | 118.9 | C16—C15—H15 | 120.6 |
C5—C4—H4 | 118.9 | C17—C16—C15 | 122.18 (16) |
C6—C5—C10 | 118.56 (17) | C17—C16—Cl | 118.45 (14) |
C6—C5—C4 | 121.40 (19) | C15—C16—Cl | 119.36 (15) |
C10—C5—C4 | 120.04 (18) | C16—C17—C18 | 118.83 (16) |
C7—C6—C5 | 120.1 (2) | C16—C17—H17 | 120.6 |
C7—C6—H6 | 119.9 | C18—C17—H17 | 120.6 |
C5—C6—H6 | 119.9 | C17—C18—C13 | 119.47 (16) |
C6—C7—C8 | 121.1 (2) | C17—C18—H18 | 120.3 |
C6—C7—H7 | 119.4 | C13—C18—H18 | 120.3 |
C8—C7—H7 | 119.4 | C12—C19—H19A | 109.5 |
C9—C8—C7 | 120.42 (18) | C12—C19—H19B | 109.5 |
C9—C8—H8 | 119.8 | H19A—C19—H19B | 109.5 |
C7—C8—H8 | 119.8 | C12—C19—H19C | 109.5 |
C8—C9—C10 | 119.4 (2) | H19A—C19—H19C | 109.5 |
C8—C9—H9 | 120.3 | H19B—C19—H19C | 109.5 |
C10—C9—H9 | 120.3 | ||
O3—S—C1—C12 | 8.85 (18) | C1—C2—C11—C10 | −178.97 (16) |
O2—S—C1—C12 | 138.51 (16) | C12—O1—C11—C2 | −0.01 (19) |
C13—S—C1—C12 | −106.87 (16) | C12—O1—C11—C10 | 179.12 (15) |
O3—S—C1—C2 | −164.41 (14) | C5—C10—C11—C2 | −0.7 (2) |
O2—S—C1—C2 | −34.74 (17) | C9—C10—C11—C2 | 179.39 (17) |
C13—S—C1—C2 | 79.88 (16) | C5—C10—C11—O1 | −179.69 (16) |
C12—C1—C2—C11 | −0.25 (19) | C9—C10—C11—O1 | 0.4 (3) |
S—C1—C2—C11 | 174.06 (13) | C11—O1—C12—C1 | −0.16 (19) |
C12—C1—C2—C3 | −179.16 (19) | C11—O1—C12—C19 | −177.64 (15) |
S—C1—C2—C3 | −4.9 (3) | C2—C1—C12—O1 | 0.26 (19) |
C11—C2—C3—C4 | 0.1 (2) | S—C1—C12—O1 | −173.98 (12) |
C1—C2—C3—C4 | 178.91 (18) | C2—C1—C12—C19 | 177.06 (19) |
C2—C3—C4—C5 | 0.2 (3) | S—C1—C12—C19 | 2.8 (3) |
C3—C4—C5—C6 | 179.21 (18) | O3—S—C13—C14 | 147.32 (16) |
C3—C4—C5—C10 | −0.7 (3) | O2—S—C13—C14 | 17.39 (18) |
C10—C5—C6—C7 | −0.5 (3) | C1—S—C13—C14 | −96.49 (16) |
C4—C5—C6—C7 | 179.54 (19) | O3—S—C13—C18 | −31.49 (16) |
C5—C6—C7—C8 | −0.1 (3) | O2—S—C13—C18 | −161.42 (14) |
C6—C7—C8—C9 | 0.4 (3) | C1—S—C13—C18 | 84.70 (16) |
C7—C8—C9—C10 | 0.0 (3) | C18—C13—C14—C15 | 1.3 (3) |
C6—C5—C10—C11 | −179.00 (16) | S—C13—C14—C15 | −177.48 (16) |
C4—C5—C10—C11 | 0.9 (2) | C13—C14—C15—C16 | 0.1 (3) |
C6—C5—C10—C9 | 0.9 (3) | C14—C15—C16—C17 | −1.1 (3) |
C4—C5—C10—C9 | −179.14 (17) | C14—C15—C16—Cl | 177.77 (16) |
C8—C9—C10—C11 | 179.23 (17) | C15—C16—C17—C18 | 0.7 (3) |
C8—C9—C10—C5 | −0.7 (3) | Cl—C16—C17—C18 | −178.19 (15) |
C3—C2—C11—O1 | 179.29 (14) | C16—C17—C18—C13 | 0.7 (3) |
C1—C2—C11—O1 | 0.16 (19) | C14—C13—C18—C17 | −1.7 (3) |
C3—C2—C11—C10 | 0.2 (3) | S—C13—C18—C17 | 177.10 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19A···Cg3i | 0.98 | 2.89 | 3.488 (3) | 120 |
C8—H8···O2ii | 0.95 | 2.48 | 3.428 (2) | 173 |
Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) −x+3/2, y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H13ClO3S |
Mr | 356.80 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 173 |
a, b, c (Å) | 8.1155 (3), 18.6014 (7), 10.8319 (4) |
V (Å3) | 1635.18 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.60 × 0.40 × 0.40 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1999) |
Tmin, Tmax | 0.842, 0.857 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9543, 2611, 2532 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.066, 1.06 |
No. of reflections | 2611 |
No. of parameters | 218 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.20 |
Absolute structure | Flack (1983), 728 Freidel pairs |
Absolute structure parameter | −0.01 (5) |
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 |
C19—H19A···Cg3i | 0.98 | 2.89 | 3.488 (3) | 120.4 |
C8—H8···O2ii | 0.95 | 2.48 | 3.428 (2) | 172.8 |
Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) −x+3/2, y+1/2, z+1/2. |
References
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This work is related to earlier communications on the synthesis and structure of 2-methylnaphtho[1,2-b]furan analogues, viz. 2-methyl-3-(methylsulfinyl) naphtho[1,2-b]furan (Choi et al., 2006) and 2-methyl-3-(phenylsulfonyl) naphtho[1,2-b]furan (Choi et al., 2008). Herein we report the molecular and crystal structure of the title compound, 3-(4-chlorophenylsulfonyl)-2-methylnaphtho[1,2-b]furan (Fig. 1).
The naphthofuran unit is essentially planar, with a mean deviation of 0.007 Å from the least-squares plane defined by the thirteen constituent atoms. The 4-chlorophenyl ring (C13-C18) makes a dihedral angle of 68.59 (5)° with the plane of the naphthofuran fragment. The crystal packing (Fig. 2) is stabilized by aromatic π—π stacking interactions between the benzene rings from the adjacent molecules. The Cg1···Cg2iii distance is 3.635 (3) Å (Cg1 and Cg2 are the centroids of the C5-C10 benzene ring and the C2/C3/C4/C5/C10/C11 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by C—H···π interactions between a methyl H atom and the furan ring of the naphthofuran unit, with a C19—H19A···Cg3i separation of 2.89 Å (Fig. 2 and Table 1; Cg3 is the centroid of the O1/C12/C1/C2/C11 furan ring; symmetry code as in Fig. 2). Additionally, intermolecular C—H···O interactions in the structure were observed (Fig. 2 and Table 1; symmetry code as in Fig. 2)