organic compounds
6-Phenylbenzo[d]naphtho[2,3-b]thiophene
aCAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai-25, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-25, India
*Correspondence e-mail: shirai2011@gmail.com
In the title compound, C22H14S, the r.m.s. deviation from the mean plane of the four-fused-ring naphthothiophene unit is 0.056 Å. The dihedral angle between the naphthothiophene plane and the pendant phenyl ring is 67.24 (6)°. In the crystal, weak C—H⋯π and π–π stacking [minimum centroid–centroid separation = 3.7466 (10) Å] interactions are observed, which together lead to (010) sheets.
Related literature
For background to the biological activity of benzothiophene derivatives, see: Isloora et al. (2010).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); 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, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812049471/hb6995sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049471/hb6995Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812049471/hb6995Isup3.cml
The benzo[b]thiophen-3-yl(2-(phenyl(pivaloyloxy)methyl)phenyl) methyl pivalate (0.73 g, 1.60 mmol) upon interaction with ZnBr2 (0.02 g, 0.13 mmol) followed by removal of solvent and column chromatographic purification (silica gel; hexane-ethyl acetate, 99:1) gave the compound as a colorless solid (0.50 g, 72%). Colourless blocks were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.
All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with C—H distances fixed in the range 0.93–0.97 Å with Uiso(H) = 1.5Ueq(C) for methyl H 1.2Ueq(C) for other H atoms.
Some benzo[b]thiophene derivatives show significant antimicrobial and anti-inflammatory activities (Isloora et al., 2010). As part of our own studies in this area, an X-ray study of the title compound was carried out.
Fig. 1 shows the ORTEP representation of the molecular structure of the title compound with atoms at the 30% probability level. The naphthothiophene moiety is almost planar with an r.m.s. deviation of fitted atoms = -0.0065 (1)°. The dihedral angle between the naphthothiophene plane and the attached benzene [C17—C22] ring is 67.24 (6)°. The thiophene ring is almost planar, with maximum deviation of 0.014 (1) Å.
In the crystal, C—H···π interactions occur (Table 1).
For background to the biological activity of benzothiophene derivatives, see: Isloora et al. (2010).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C22H14S | F(000) = 1296 |
Mr = 310.40 | Dx = 1.329 Mg m−3 |
Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 3855 reflections |
a = 12.6752 (10) Å | θ = 1.8–28.4° |
b = 28.578 (2) Å | µ = 0.21 mm−1 |
c = 8.5659 (6) Å | T = 293 K |
V = 3102.8 (4) Å3 | Block, colourless |
Z = 8 | 0.20 × 0.20 × 0.20 mm |
Bruker APEXII CCD diffractometer | 2892 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 28.4°, θmin = 1.8° |
ω and φ scans | h = −16→16 |
16518 measured reflections | k = −34→38 |
3855 independent reflections | l = −9→11 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0571P)2 + 0.6864P] where P = (Fo2 + 2Fc2)/3 |
3855 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C22H14S | V = 3102.8 (4) Å3 |
Mr = 310.40 | Z = 8 |
Orthorhombic, Pccn | Mo Kα radiation |
a = 12.6752 (10) Å | µ = 0.21 mm−1 |
b = 28.578 (2) Å | T = 293 K |
c = 8.5659 (6) Å | 0.20 × 0.20 × 0.20 mm |
Bruker APEXII CCD diffractometer | 2892 reflections with I > 2σ(I) |
16518 measured reflections | Rint = 0.031 |
3855 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.21 e Å−3 |
3855 reflections | Δρmin = −0.24 e Å−3 |
208 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.49436 (3) | 0.039709 (15) | 0.71196 (5) | 0.04701 (14) | |
C11 | 0.34912 (11) | 0.12197 (5) | 1.10829 (17) | 0.0367 (3) | |
C10 | 0.41403 (11) | 0.14729 (5) | 1.00101 (17) | 0.0361 (3) | |
C17 | 0.52550 (12) | 0.14890 (5) | 0.75491 (18) | 0.0375 (3) | |
C7 | 0.37407 (11) | 0.05119 (5) | 0.95979 (18) | 0.0376 (3) | |
C9 | 0.46095 (11) | 0.12338 (5) | 0.87264 (17) | 0.0361 (3) | |
C13 | 0.30387 (12) | 0.14611 (6) | 1.23609 (19) | 0.0444 (4) | |
H13 | 0.2633 | 0.1297 | 1.3080 | 0.053* | |
C8 | 0.44145 (11) | 0.07613 (5) | 0.85662 (17) | 0.0369 (3) | |
C22 | 0.62230 (13) | 0.16834 (6) | 0.7927 (2) | 0.0471 (4) | |
H22 | 0.6492 | 0.1648 | 0.8930 | 0.057* | |
C1 | 0.42526 (12) | −0.00859 (5) | 0.78516 (19) | 0.0411 (3) | |
C6 | 0.36343 (12) | 0.00252 (5) | 0.91445 (18) | 0.0388 (3) | |
C12 | 0.32950 (12) | 0.07416 (5) | 1.08341 (19) | 0.0397 (3) | |
H12 | 0.2857 | 0.0579 | 1.1517 | 0.048* | |
C16 | 0.42662 (13) | 0.19611 (6) | 1.0261 (2) | 0.0437 (4) | |
H16 | 0.4677 | 0.2134 | 0.9572 | 0.052* | |
C18 | 0.48824 (13) | 0.15417 (6) | 0.6039 (2) | 0.0457 (4) | |
H18 | 0.4244 | 0.1406 | 0.5755 | 0.055* | |
C19 | 0.54498 (15) | 0.17947 (7) | 0.4950 (2) | 0.0533 (4) | |
H19 | 0.5189 | 0.1832 | 0.3943 | 0.064* | |
C5 | 0.30009 (14) | −0.03191 (6) | 0.9809 (2) | 0.0491 (4) | |
H5 | 0.2582 | −0.0250 | 1.0670 | 0.059* | |
C20 | 0.63982 (15) | 0.19908 (6) | 0.5357 (2) | 0.0528 (4) | |
H20 | 0.6774 | 0.2166 | 0.4629 | 0.063* | |
C15 | 0.37981 (14) | 0.21805 (6) | 1.1489 (2) | 0.0499 (4) | |
H15 | 0.3886 | 0.2501 | 1.1620 | 0.060* | |
C2 | 0.42771 (15) | −0.05383 (6) | 0.7253 (2) | 0.0493 (4) | |
H2 | 0.4712 | −0.0614 | 0.6415 | 0.059* | |
C21 | 0.67926 (14) | 0.19303 (6) | 0.6823 (2) | 0.0536 (4) | |
H21 | 0.7447 | 0.2056 | 0.7083 | 0.064* | |
C3 | 0.36430 (15) | −0.08691 (6) | 0.7931 (2) | 0.0539 (5) | |
H3 | 0.3645 | −0.1173 | 0.7539 | 0.065* | |
C4 | 0.29989 (15) | −0.07614 (6) | 0.9188 (2) | 0.0554 (5) | |
H4 | 0.2563 | −0.0990 | 0.9613 | 0.066* | |
C14 | 0.31846 (14) | 0.19275 (6) | 1.2558 (2) | 0.0501 (4) | |
H14 | 0.2877 | 0.2080 | 1.3403 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0557 (3) | 0.0449 (2) | 0.0404 (3) | −0.00271 (18) | 0.01194 (18) | −0.00246 (18) |
C11 | 0.0346 (7) | 0.0416 (8) | 0.0341 (8) | 0.0018 (6) | −0.0010 (6) | 0.0011 (6) |
C10 | 0.0347 (7) | 0.0395 (8) | 0.0340 (8) | 0.0009 (6) | −0.0037 (6) | 0.0022 (6) |
C17 | 0.0415 (8) | 0.0346 (8) | 0.0365 (8) | 0.0008 (6) | 0.0039 (6) | 0.0026 (6) |
C7 | 0.0372 (7) | 0.0384 (8) | 0.0371 (8) | −0.0013 (6) | −0.0001 (6) | 0.0039 (6) |
C9 | 0.0355 (7) | 0.0395 (8) | 0.0333 (8) | −0.0024 (6) | −0.0016 (6) | 0.0037 (6) |
C13 | 0.0418 (8) | 0.0510 (10) | 0.0404 (9) | 0.0017 (7) | 0.0051 (7) | −0.0001 (7) |
C8 | 0.0382 (7) | 0.0394 (8) | 0.0332 (8) | 0.0001 (6) | 0.0013 (6) | 0.0010 (6) |
C22 | 0.0508 (9) | 0.0483 (9) | 0.0423 (9) | −0.0087 (7) | −0.0026 (7) | 0.0066 (8) |
C1 | 0.0437 (8) | 0.0392 (8) | 0.0403 (9) | 0.0014 (6) | −0.0038 (7) | 0.0014 (7) |
C6 | 0.0416 (8) | 0.0356 (8) | 0.0391 (8) | 0.0010 (6) | −0.0025 (6) | 0.0028 (6) |
C12 | 0.0392 (7) | 0.0410 (8) | 0.0390 (8) | −0.0020 (6) | 0.0050 (6) | 0.0055 (7) |
C16 | 0.0485 (8) | 0.0392 (8) | 0.0435 (9) | −0.0025 (7) | −0.0016 (7) | 0.0033 (7) |
C18 | 0.0454 (8) | 0.0521 (10) | 0.0397 (9) | −0.0004 (7) | 0.0008 (7) | 0.0042 (7) |
C19 | 0.0608 (10) | 0.0604 (11) | 0.0386 (9) | 0.0084 (9) | 0.0052 (8) | 0.0102 (8) |
C5 | 0.0555 (10) | 0.0402 (9) | 0.0516 (10) | −0.0024 (7) | 0.0069 (8) | 0.0044 (7) |
C20 | 0.0602 (10) | 0.0450 (9) | 0.0533 (11) | −0.0006 (8) | 0.0188 (9) | 0.0111 (8) |
C15 | 0.0582 (10) | 0.0401 (9) | 0.0515 (10) | 0.0023 (7) | −0.0028 (8) | −0.0043 (8) |
C2 | 0.0580 (10) | 0.0445 (9) | 0.0454 (10) | 0.0083 (8) | −0.0041 (8) | −0.0043 (8) |
C21 | 0.0518 (9) | 0.0504 (10) | 0.0585 (11) | −0.0133 (8) | 0.0052 (8) | 0.0055 (9) |
C3 | 0.0692 (11) | 0.0344 (8) | 0.0580 (11) | 0.0036 (8) | −0.0092 (9) | −0.0027 (8) |
C4 | 0.0653 (11) | 0.0384 (9) | 0.0625 (12) | −0.0048 (8) | 0.0017 (9) | 0.0067 (8) |
C14 | 0.0538 (10) | 0.0511 (10) | 0.0455 (10) | 0.0071 (8) | 0.0040 (8) | −0.0098 (8) |
S1—C1 | 1.7508 (16) | C12—H12 | 0.9300 |
S1—C8 | 1.7518 (15) | C16—C15 | 1.360 (2) |
C11—C12 | 1.405 (2) | C16—H16 | 0.9300 |
C11—C13 | 1.415 (2) | C18—C19 | 1.382 (2) |
C11—C10 | 1.430 (2) | C18—H18 | 0.9300 |
C10—C16 | 1.421 (2) | C19—C20 | 1.371 (3) |
C10—C9 | 1.425 (2) | C19—H19 | 0.9300 |
C17—C22 | 1.385 (2) | C5—C4 | 1.372 (2) |
C17—C18 | 1.385 (2) | C5—H5 | 0.9300 |
C17—C9 | 1.489 (2) | C20—C21 | 1.363 (3) |
C7—C12 | 1.368 (2) | C20—H20 | 0.9300 |
C7—C8 | 1.421 (2) | C15—C14 | 1.402 (2) |
C7—C6 | 1.450 (2) | C15—H15 | 0.9300 |
C9—C8 | 1.380 (2) | C2—C3 | 1.370 (3) |
C13—C14 | 1.356 (2) | C2—H2 | 0.9300 |
C13—H13 | 0.9300 | C21—H21 | 0.9300 |
C22—C21 | 1.383 (2) | C3—C4 | 1.386 (3) |
C22—H22 | 0.9300 | C3—H3 | 0.9300 |
C1—C2 | 1.391 (2) | C4—H4 | 0.9300 |
C1—C6 | 1.393 (2) | C14—H14 | 0.9300 |
C6—C5 | 1.392 (2) | ||
C1—S1—C8 | 91.35 (7) | C15—C16—C10 | 121.39 (15) |
C12—C11—C13 | 121.30 (14) | C15—C16—H16 | 119.3 |
C12—C11—C10 | 119.76 (13) | C10—C16—H16 | 119.3 |
C13—C11—C10 | 118.92 (14) | C19—C18—C17 | 120.63 (16) |
C16—C10—C9 | 122.76 (14) | C19—C18—H18 | 119.7 |
C16—C10—C11 | 117.65 (14) | C17—C18—H18 | 119.7 |
C9—C10—C11 | 119.57 (13) | C20—C19—C18 | 119.93 (17) |
C22—C17—C18 | 118.47 (14) | C20—C19—H19 | 120.0 |
C22—C17—C9 | 121.64 (14) | C18—C19—H19 | 120.0 |
C18—C17—C9 | 119.89 (14) | C4—C5—C6 | 119.59 (17) |
C12—C7—C8 | 119.28 (14) | C4—C5—H5 | 120.2 |
C12—C7—C6 | 128.98 (14) | C6—C5—H5 | 120.2 |
C8—C7—C6 | 111.74 (13) | C21—C20—C19 | 120.25 (16) |
C8—C9—C10 | 118.13 (13) | C21—C20—H20 | 119.9 |
C8—C9—C17 | 120.69 (14) | C19—C20—H20 | 119.9 |
C10—C9—C17 | 121.14 (13) | C16—C15—C14 | 120.59 (16) |
C14—C13—C11 | 121.33 (16) | C16—C15—H15 | 119.7 |
C14—C13—H13 | 119.3 | C14—C15—H15 | 119.7 |
C11—C13—H13 | 119.3 | C3—C2—C1 | 118.14 (17) |
C9—C8—C7 | 122.47 (14) | C3—C2—H2 | 120.9 |
C9—C8—S1 | 125.69 (12) | C1—C2—H2 | 120.9 |
C7—C8—S1 | 111.84 (11) | C20—C21—C22 | 120.21 (16) |
C21—C22—C17 | 120.47 (16) | C20—C21—H21 | 119.9 |
C21—C22—H22 | 119.8 | C22—C21—H21 | 119.9 |
C17—C22—H22 | 119.8 | C2—C3—C4 | 121.47 (16) |
C2—C1—C6 | 121.15 (15) | C2—C3—H3 | 119.3 |
C2—C1—S1 | 126.11 (13) | C4—C3—H3 | 119.3 |
C6—C1—S1 | 112.73 (12) | C5—C4—C3 | 120.33 (17) |
C5—C6—C1 | 119.26 (15) | C5—C4—H4 | 119.8 |
C5—C6—C7 | 128.46 (15) | C3—C4—H4 | 119.8 |
C1—C6—C7 | 112.27 (13) | C13—C14—C15 | 120.07 (16) |
C7—C12—C11 | 120.72 (14) | C13—C14—H14 | 120.0 |
C7—C12—H12 | 119.6 | C15—C14—H14 | 120.0 |
C11—C12—H12 | 119.6 | ||
C12—C11—C10—C16 | 176.46 (14) | S1—C1—C6—C5 | 177.03 (13) |
C13—C11—C10—C16 | −2.1 (2) | C2—C1—C6—C7 | 178.72 (14) |
C12—C11—C10—C9 | −2.0 (2) | S1—C1—C6—C7 | −1.81 (17) |
C13—C11—C10—C9 | 179.41 (13) | C12—C7—C6—C5 | 4.2 (3) |
C16—C10—C9—C8 | −178.29 (14) | C8—C7—C6—C5 | −176.05 (16) |
C11—C10—C9—C8 | 0.1 (2) | C12—C7—C6—C1 | −177.08 (15) |
C16—C10—C9—C17 | −0.9 (2) | C8—C7—C6—C1 | 2.66 (19) |
C11—C10—C9—C17 | 177.53 (13) | C8—C7—C12—C11 | 0.5 (2) |
C22—C17—C9—C8 | −114.77 (18) | C6—C7—C12—C11 | −179.82 (15) |
C18—C17—C9—C8 | 66.1 (2) | C13—C11—C12—C7 | −179.73 (14) |
C22—C17—C9—C10 | 67.9 (2) | C10—C11—C12—C7 | 1.7 (2) |
C18—C17—C9—C10 | −111.22 (17) | C9—C10—C16—C15 | 179.23 (15) |
C12—C11—C13—C14 | −176.64 (16) | C11—C10—C16—C15 | 0.8 (2) |
C10—C11—C13—C14 | 1.9 (2) | C22—C17—C18—C19 | −2.0 (2) |
C10—C9—C8—C7 | 2.1 (2) | C9—C17—C18—C19 | 177.19 (16) |
C17—C9—C8—C7 | −175.29 (14) | C17—C18—C19—C20 | 0.9 (3) |
C10—C9—C8—S1 | −177.76 (11) | C1—C6—C5—C4 | 0.3 (3) |
C17—C9—C8—S1 | 4.8 (2) | C7—C6—C5—C4 | 178.93 (16) |
C12—C7—C8—C9 | −2.5 (2) | C18—C19—C20—C21 | 1.1 (3) |
C6—C7—C8—C9 | 177.76 (14) | C10—C16—C15—C14 | 0.8 (3) |
C12—C7—C8—S1 | 177.44 (12) | C6—C1—C2—C3 | 2.6 (2) |
C6—C7—C8—S1 | −2.33 (16) | S1—C1—C2—C3 | −176.83 (13) |
C1—S1—C8—C9 | −178.97 (14) | C19—C20—C21—C22 | −2.1 (3) |
C1—S1—C8—C7 | 1.12 (12) | C17—C22—C21—C20 | 1.0 (3) |
C18—C17—C22—C21 | 1.0 (3) | C1—C2—C3—C4 | −0.6 (3) |
C9—C17—C22—C21 | −178.11 (16) | C6—C5—C4—C3 | 1.6 (3) |
C8—S1—C1—C2 | 179.84 (15) | C2—C3—C4—C5 | −1.5 (3) |
C8—S1—C1—C6 | 0.41 (12) | C11—C13—C14—C15 | −0.3 (3) |
C2—C1—C6—C5 | −2.4 (2) | C16—C15—C14—C13 | −1.1 (3) |
Cg2 and Cg3 are the centroids of the C1-C6 and C10–C16 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg2i | 0.93 | 2.94 | 3.8138 (19) | 158 |
C13—H13···Cg3i | 0.93 | 2.64 | 3.5399 (17) | 163 |
Symmetry code: (i) −x−1/2, y, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H14S |
Mr | 310.40 |
Crystal system, space group | Orthorhombic, Pccn |
Temperature (K) | 293 |
a, b, c (Å) | 12.6752 (10), 28.578 (2), 8.5659 (6) |
V (Å3) | 3102.8 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.20 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16518, 3855, 2892 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.118, 1.03 |
No. of reflections | 3855 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.24 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg2 and Cg3 are the centroids of the C1-C6 and C10–C16 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg2i | 0.93 | 2.94 | 3.8138 (19) | 158 |
C13—H13···Cg3i | 0.93 | 2.64 | 3.5399 (17) | 163 |
Symmetry code: (i) −x−1/2, y, z−1/2. |
Acknowledgements
VS and DV thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, and the UGC SAP for the facilities to the department.
References
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Some benzo[b]thiophene derivatives show significant antimicrobial and anti-inflammatory activities (Isloora et al., 2010). As part of our own studies in this area, an X-ray study of the title compound was carried out.
Fig. 1 shows the ORTEP representation of the molecular structure of the title compound with atoms at the 30% probability level. The naphthothiophene moiety is almost planar with an r.m.s. deviation of fitted atoms = -0.0065 (1)°. The dihedral angle between the naphthothiophene plane and the attached benzene [C17—C22] ring is 67.24 (6)°. The thiophene ring is almost planar, with maximum deviation of 0.014 (1) Å.
In the crystal, C—H···π interactions occur (Table 1).