The title compounds, 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene and 7-phenylanthra[2,3-b]benzo[d]thiophene, are benzothiophene derivatives in which the benzothiophene moiety is fused with a naphthalene ring system in the former and with an anthracene ring system in the latter. In the former, the 4-methylbenzene ring substituent makes a dihedral angle of 71.40 (9)° with the mean plane of the naphthalene ring system, while the phenyl ring substituent in the latter makes a dihedral angle of 67.08 (12)° with the mean plane of the anthracene ring system.
Keywords: crystal structure; benzothiophene; benzo[b]naphtho[2,3-d]thiophene; anthra[2,3-b]benzo[d]thiophene; C—H⋯π interactions; offset π–π interactions
Abstract
The title compounds, C23H16S, (I), and C26H16S, (II), are benzothiophene derivatives in which the benzothiophene moiety is fused with a naphthalene ring system in (I), and with an anthracene ring system in (II). In (I), the mean plane of the benzothiophene ring system makes a dihedral angle of 2.28 (6)° with the naphthalene ring system, and a dihedral angle of 1.28 (6)° with the anthracene ring system in (II), showing that the fused units are essentially planar. In (I), the 4-methylbenzene ring substituent makes a dihedral angle of 71.40 (9)° with the naphthalene ring system, while the phenyl ring substituent in (II) makes a dihedral angle of 67.08 (12)° with the anthracene ring system. In the crystals of both compounds, molecules are linked by C—H⋯π interactions, leading to the formation of slabs parallel to (001) in (I) and to zigzag chains along [001] in (II). There are also offset π–π interactions present within the slabs in (I). In the crystal of (II), they link the chains, forming sheets parallel to (010). The triclinic polymorph of compound (II) has been reported [Sivasakthikumaran et al., (2012 ▸). J. Org. Chem. 77, 9053–9071].
Chemical context
The thiophene nucleus has been shown to be an important heterocyclic unit in compounds possessing promising pharmacological characteristics, such as anti-HIV PR inhibitors (Bonini et al., 2005 ▸) and anti-breast cancer (Brault et al., 2005 ▸) activities. Benzothiophenes are important biologically active molecules. One of the most important drugs based on the benzothiophene system is Raloxifine, used for the prevention and treatment of osteoporosis in postmenopausal women (Jordan, 2003 ▸). Benzothiophenes are also present in luminescent components used in organic materials (Russell & Press, 1996 ▸).
Naphtho[2,3-b]thiophene derivatives have been found to exhibit antiproliferative activity related to the inhibition of tublin polymerization (Zuse et al., 2007 ▸, 2006 ▸). As a result of their outstanding electronic testability and considerable chemical and environmental stability, thiophene derivatives have been widely used in solar cells (Justin Thomas et al., 2008 ▸; Hänsel et al., 2003 ▸), organic light-emitting diodes (OLEDs) (Mazzeo et al., 2003 ▸), organic field-effect transistors (OFETs) (Zhan et al., 2007 ▸) and as NLO devices (Bedworth et al., 1996 ▸; Raposo et al., 2011 ▸).Against this background, we describe herein the syntheses and crystal structures of the title benzothiophene derivatives. 
Structural commentary
The molecular structures of the title compounds, (I) and (II), are illustrated in Figs. 1 ▸ and 2 ▸, respectively. In both compounds, the benzothiophene ring systems are almost planar with the dihedral angles between the benzene and thiophene rings being 1.85 (11)° in (I) and 0.56 (18)° in (II).
Figure 1.
The molecular structure of compound (I), showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
Figure 2.
The molecular structure of compound (II), showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
In compound (I), the naphthalene ring system (atoms C1–C3/C10–C16) (r.m.s. deviation = 0.006 Å) makes a a dihedral angle of 2.28 (6)° with the benzothiophene (C3–C10/S1) ring system (r.m.s. deviation = 0.023 Å). The 4-methylbenzene ring substituent (C17–C22) makes a dihedral angle of 71.40 (9)° with the naphthalene ring system
In compound (II), the anthracene ring system (C1–C3/C10–C20) is almost planar (r.m.s. deviation = 0.075 Å) and makes a a dihedral angle of 7.31 (9)° with the benzothiophene (C3–C10/S1) ring system (r.m.s. deviation = 0.012 Å). Here, the phenyl ring substituent (C21–C26) in (II) makes a dihedral angle of 67.08 (12)° with the anthracene ring system, and the anthracene ring is (−)antiperiplanar with respect to the benzothiophene moiety, as indicated by the S1—C3—C10—C11 torsion angle of −176.4 (2)°.
In the triclinic polymorph of compound (II) (Sivasakthikumaran et al., 2012 ▸), the major component of the disordered phenyl ring substituent makes a dihedral angle of 79.39 (12)° with the anthracene ring system.
Supramolecular features
In the crystals of both compounds, molecules are linked by C—H⋯π interactions (see Tables 1 ▸ and 2 ▸), leading to the formation of slabs parallel to (001) in (I), and to zigzag chains along [001] in (II); as illustrated in Figs. 3 ▸, 4 ▸ and 5 ▸. There are also offset π–π interactions present within the slabs in (I) [Cg1⋯Cg3i = 3.629 (1) Å, interplanar distance = 3.602 (1) Å, slippage = 0.49 Å; Cg2⋯Cg4ii = 3.983 (1), interplanar distance = 3.473 (1), slippage 1.79 Å; Cg1, Cg2, Cg3 and Cg4 are the centroids of rings S1/C3/C4/C9/C10, C1–C3/C10–C12, C1/C12–C16 and C4–C9, respectively; symmetry codes: (i) x + 1, y, z; (ii) x − 1, y, z]. In the crystal of (II), offset π–π interactions link the chains, forming sheets parallel to (010) [Cg2⋯Cg4iii = 3.711 (2) Å, interplanar distance = 3.479 (1) Å, slippage = 1.21 Å; Cg3⋯Cg4iii = 3.741 (2) Å, interplanar distance = 3.443 (1) Å, slippage = 1.22 Å; Cg2, Cg3 and Cg4 are the centroids of rings C1–C3/C10–C12, C1/C12–C16 and C4–C9, respectively; symmetry code: (iii) −x + 1, −y + 1, −z + 1].
Table 1. Hydrogen-bond geometry (Å, °) for (I) .
Cg3, Cg4 and Cg5 are the centroids of rings (C1/C12–C16), (C4–C6) and (C17–C22), respectively.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C15—H15⋯Cg5i | 0.93 | 2.94 | 3.763 (3) | 148 |
| C19—H19⋯Cg4ii | 0.93 | 2.94 | 3.753 (3) | 147 |
| C21—H21⋯Cg3iii | 0.93 | 2.91 | 3.721 (3) | 146 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Table 2. Hydrogen-bond geometry (Å, °) for (II) .
Cg2 and Cg3 are the centroids of rings (C1–C3/C10–C12) and (C1/C12–C14/C19/C20), respectively.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C13—H13⋯Cg2i | 0.93 | 2.97 | 3.885 (4) | 168 |
| C15—H15⋯Cg3i | 0.93 | 2.57 | 3.479 (4) | 166 |
Symmetry code: (i) 
.
Figure 3.
The crystal packing of compound (I). The C—H⋯π interactions are shown as dashed lines (see Table 1 ▸ for details). H atoms not involved in these interactions have been omitted for clarity.
Figure 4.
The crystal packing of compound (II), viewed along the b axis. The C—H⋯π interactions are shown as dashed lines (see Table 2 ▸ for details) and the centroids as brown balls. H atoms not involved in these interactions have been omitted for clarity.
Figure 5.
The crystal packing of compound (I), viewed along the c axis, showing the C—H⋯π interactions (represented as turquoise lines) leading to the formation of slabs parallel to (001).
Database survey
A search of the Cambridge Structural Database (Version 5.38, update May 2016; Groom et al., 2016 ▸) for the naphthobenzothiophene skeleton gave 32 hits. Among these there are five naphthobenzothiophene derivatives that resemble compound (I), viz. 6-(phenyl)benzo[b]naphtho[2,3-d]thiophene (NEQMAZ; Silambarasan et al., 2013 ▸), 6-(4-methoxyphenyl)benzo[b]naphtho[2,3-d]thiophene (PECQEV; Silambarasan et al., 2012 ▸), 6-(2-thienyl)benzo[b]naphtho[2,3-d]thiophene (XIMZUQ; Sivasakthikumaran et al., 2012 ▸), 6-(1-benzothiophen-3-yl)benzo[b]naphtho[2,3-d]thiophene (HIXQUB; Li et al., 2007 ▸) and 1,3-dimethylbenzo[b]naphtho[2,3-d]thiophene (ROMPUF/ROMPUF01; Umarani et al., 2009/Dhayalan et al., 2009 ▸). There are also two anthracene analogues, viz. anthra[2,3-b]benzo[d]thiophene itself (JOHSOP; Du et al., 2008 ▸), and 7-(1-benzothiophen-2-yl)anthra[2,3-b]benzo[d]thiophene (FOLGEU; Rafiq et al., 2014 ▸); as well as the triclinic polymorph of compound (II) (XIMZOK; Sivasakthikumaran et al., 2012 ▸).
Synthesis and crystallization
Compound (I)
The reduction of the diketone (benzothiophen-3-yl)[2-(4-methylbenzoyl)phenyl]methanone (0.85 g, 2.38 mmol) using sodium borohydride (0.49 g, 12.89 mmol) followed by work-up gave the diol. Dipivaloylation of the diol (0.77 g, 2.31 mmol) using pivaloyl chloride (1.39 g, 11.52 mmol) and triethylamine (4.69 g, 45.20 mmol) in the presence of a catalytic amount of DMAP (10 mg) in dry DCM (20 ml) led to the isolation of dipivalate (benzo[b]thiophen-3-yl){2-[pivaloyloxy(p-tolyl) methyl]phenyl}methyl pivalate as a viscous liquid. Dipivalate (benzo[b]thiophen-3-yl){2-[pivaloyloxy(p-toyl) methyl]phenyl}methyl pivalate (0.98 g, 1.96 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 6-(p-tolyl)benzo[b]naphtho[2,3-d]thiophene as a pale-green solid (yield 0.53 g, 78%). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of (I) in ethyl acetate at room temperature (m.p. 391–393 K).
Compound (II)
The reduction of the diketone (2-benzoylphenyl)(dibenzo[b,d]thiophen-2-yl)methanone (1.11 g, 2.38 mmol) using sodium borohydride (0.53 g, 13.94 mmol) followed by work-up gave the diol. Dipivaloylation of the diol (1.12 g, 2.82 mmol) using pivaloyl chloride (1.70 g, 14.14 mmol) and triethylamine (5.72 g, 56.56 mmol) in the presence of a catalytic amount of DMAP (10 mg) in dry DCM (20 ml) led to the isolation of dipivalate (dibenzo[b,d]thiophen-2-yl){2-[phenyl(pivaloyloxy)methyl]phenyl}methyl pivalate as a thick liquid. Dipivalate (dibenzo[b,d]thiophen-2-yl){2-[phenyl(pivaloyloxy)methyl]phenyl}methyl pivalate (1.28 g, 2.26 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 a new orthorhombic polymorph of 7-phenylanthra[2,3-b]benzo[d]thiophene (yield 0.83 g, 72%) as a yellow solid. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the compound (II) in ethyl acetate at room temperature (m.p. 463–465 K).
Refinement
Crystal data, data collection and structure refinement details for compounds (I) and (II) are summarized in Table 3 ▸. The C-bound H atoms were included in calculated positions and treated as riding atoms, with C—H = 0.93–0.96 Å and with U iso(H) = 1.5U eq(methyl C) and 1.2U eq(C) for other H atoms.
Table 3. Experimental details.
| (I) | (II) | |
|---|---|---|
| Crystal data | ||
| Chemical formula | C23H16S | C26H16S |
| M r | 324.42 | 360.45 |
| Crystal system, space group | Triclinic, P
|
Orthorhombic, P c c n |
| Temperature (K) | 296 | 296 |
| a, b, c (Å) | 6.2404 (3), 11.1725 (6), 12.9987 (7) | 12.2159 (8), 33.1138 (4), 8.8993 (5) |
| α, β, γ (°) | 109.284 (2), 100.233 (4), 93.925 (2) | 90, 90, 90 |
| V (Å3) | 833.90 (8) | 3599.9 (3) |
| Z | 2 | 8 |
| Radiation type | Mo Kα | Mo Kα |
| μ (mm−1) | 0.19 | 0.19 |
| Crystal size (mm) | 0.30 × 0.25 × 0.20 | 0.30 × 0.25 × 0.25 |
| Data collection | ||
| Diffractometer | Bruker Kappa APEXII CCD | Bruker Kappa APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2008 ▸) | Multi-scan (SADABS; Bruker, 2008 ▸) |
| T min, T max | 0.944, 0.962 | 0.946, 0.955 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 15861, 2944, 2407 | 43542, 3171, 2540 |
| R int | 0.024 | 0.036 |
| (sin θ/λ)max (Å−1) | 0.595 | 0.595 |
| Refinement | ||
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.039, 0.113, 1.07 | 0.059, 0.182, 1.04 |
| No. of reflections | 2944 | 3171 |
| No. of parameters | 218 | 244 |
| H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.21, −0.21 | 1.06, −0.40 |
Supplementary Material
Crystal structure: contains datablock(s) I, II, global. DOI: 10.1107/S2056989016012937/lh5819sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016012937/lh5819Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989016012937/lh5819IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989016012937/lh5819Isup4.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank Dr Jagan and Dr Babu Varghese, Senior Scientific Officers, SAIF, IIT Madras, Chennai, India, for the data collection.
supplementary crystallographic information
(I) 6-(p-Tolyl)benzo[b]naphtho[2,3-d]thiophene . Crystal data
| C23H16S | Z = 2 |
| Mr = 324.42 | F(000) = 340 |
| Triclinic, P1 | Dx = 1.292 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 6.2404 (3) Å | Cell parameters from 2944 reflections |
| b = 11.1725 (6) Å | θ = 2.1–25.0° |
| c = 12.9987 (7) Å | µ = 0.19 mm−1 |
| α = 109.284 (2)° | T = 296 K |
| β = 100.233 (4)° | Block, colourless |
| γ = 93.925 (2)° | 0.30 × 0.25 × 0.20 mm |
| V = 833.90 (8) Å3 |
(I) 6-(p-Tolyl)benzo[b]naphtho[2,3-d]thiophene . Data collection
| Bruker Kappa APEXII CCD diffractometer | 2944 independent reflections |
| Radiation source: fine-focus sealed tube | 2407 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.024 |
| ω & φ scans | θmax = 25.0°, θmin = 2.1° |
| Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −7→7 |
| Tmin = 0.944, Tmax = 0.962 | k = −13→13 |
| 15861 measured reflections | l = −15→15 |
(I) 6-(p-Tolyl)benzo[b]naphtho[2,3-d]thiophene . Refinement
| 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: inferred from neighbouring sites |
| wR(F2) = 0.113 | H-atom parameters constrained |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.0484P)2 + 0.4189P] where P = (Fo2 + 2Fc2)/3 |
| 2944 reflections | (Δ/σ)max = 0.002 |
| 218 parameters | Δρmax = 0.21 e Å−3 |
| 0 restraints | Δρmin = −0.21 e Å−3 |
(I) 6-(p-Tolyl)benzo[b]naphtho[2,3-d]thiophene . Special details
| 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. |
(I) 6-(p-Tolyl)benzo[b]naphtho[2,3-d]thiophene . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | −0.1614 (3) | 0.24648 (18) | 0.15929 (16) | 0.0358 (4) | |
| C2 | −0.0247 (3) | 0.27515 (17) | 0.09112 (15) | 0.0344 (4) | |
| C3 | 0.1606 (3) | 0.36306 (18) | 0.14305 (15) | 0.0355 (4) | |
| C4 | 0.5130 (3) | 0.51269 (19) | 0.20179 (16) | 0.0401 (5) | |
| C5 | 0.7116 (3) | 0.5852 (2) | 0.21532 (19) | 0.0504 (5) | |
| H5 | 0.7718 | 0.5822 | 0.1541 | 0.060* | |
| C6 | 0.8178 (4) | 0.6618 (2) | 0.3211 (2) | 0.0566 (6) | |
| H6 | 0.9518 | 0.7108 | 0.3316 | 0.068* | |
| C7 | 0.7283 (4) | 0.6671 (2) | 0.4127 (2) | 0.0551 (6) | |
| H7 | 0.8012 | 0.7209 | 0.4835 | 0.066* | |
| C8 | 0.5328 (4) | 0.5937 (2) | 0.39951 (18) | 0.0474 (5) | |
| H8 | 0.4743 | 0.5970 | 0.4612 | 0.057* | |
| C9 | 0.4228 (3) | 0.51430 (18) | 0.29316 (16) | 0.0380 (4) | |
| C10 | 0.2200 (3) | 0.42696 (18) | 0.26060 (15) | 0.0360 (4) | |
| C11 | 0.0889 (3) | 0.39891 (19) | 0.32582 (16) | 0.0403 (5) | |
| H11 | 0.1264 | 0.4399 | 0.4028 | 0.048* | |
| C12 | −0.1012 (3) | 0.30925 (19) | 0.27797 (16) | 0.0390 (4) | |
| C13 | −0.2388 (4) | 0.2784 (2) | 0.34417 (18) | 0.0485 (5) | |
| H13 | −0.2009 | 0.3178 | 0.4213 | 0.058* | |
| C14 | −0.4235 (4) | 0.1932 (2) | 0.2978 (2) | 0.0544 (6) | |
| H14 | −0.5116 | 0.1752 | 0.3430 | 0.065* | |
| C15 | −0.4829 (4) | 0.1316 (2) | 0.1815 (2) | 0.0513 (5) | |
| H15 | −0.6102 | 0.0729 | 0.1500 | 0.062* | |
| C16 | −0.3550 (3) | 0.1575 (2) | 0.11515 (18) | 0.0437 (5) | |
| H16 | −0.3963 | 0.1154 | 0.0384 | 0.052* | |
| C17 | −0.0765 (3) | 0.21177 (18) | −0.03270 (15) | 0.0359 (4) | |
| C18 | −0.2468 (4) | 0.2399 (2) | −0.10000 (18) | 0.0514 (6) | |
| H18 | −0.3361 | 0.2983 | −0.0676 | 0.062* | |
| C19 | −0.2881 (4) | 0.1835 (2) | −0.21439 (18) | 0.0560 (6) | |
| H19 | −0.4042 | 0.2049 | −0.2576 | 0.067* | |
| C20 | −0.1618 (4) | 0.0964 (2) | −0.26596 (17) | 0.0467 (5) | |
| C21 | 0.0061 (4) | 0.0673 (2) | −0.19921 (19) | 0.0565 (6) | |
| H21 | 0.0935 | 0.0079 | −0.2319 | 0.068* | |
| C22 | 0.0493 (4) | 0.1237 (2) | −0.08442 (18) | 0.0514 (6) | |
| H22 | 0.1652 | 0.1019 | −0.0415 | 0.062* | |
| C23 | −0.2067 (5) | 0.0357 (3) | −0.3913 (2) | 0.0739 (8) | |
| H23A | −0.0779 | 0.0023 | −0.4136 | 0.111* | |
| H23B | −0.2443 | 0.0987 | −0.4243 | 0.111* | |
| H23C | −0.3267 | −0.0327 | −0.4158 | 0.111* | |
| S1 | 0.35084 (8) | 0.41019 (5) | 0.07515 (4) | 0.04430 (18) |
(I) 6-(p-Tolyl)benzo[b]naphtho[2,3-d]thiophene . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0382 (10) | 0.0343 (10) | 0.0370 (10) | 0.0107 (8) | 0.0085 (8) | 0.0139 (8) |
| C2 | 0.0387 (10) | 0.0344 (10) | 0.0318 (10) | 0.0126 (8) | 0.0081 (8) | 0.0119 (8) |
| C3 | 0.0390 (10) | 0.0391 (11) | 0.0328 (10) | 0.0127 (8) | 0.0120 (8) | 0.0146 (8) |
| C4 | 0.0435 (11) | 0.0410 (11) | 0.0404 (11) | 0.0097 (9) | 0.0095 (9) | 0.0192 (9) |
| C5 | 0.0487 (12) | 0.0581 (14) | 0.0534 (13) | 0.0031 (10) | 0.0127 (10) | 0.0311 (11) |
| C6 | 0.0513 (13) | 0.0559 (14) | 0.0643 (16) | −0.0075 (11) | 0.0046 (11) | 0.0300 (12) |
| C7 | 0.0601 (14) | 0.0463 (13) | 0.0496 (13) | −0.0078 (11) | −0.0010 (11) | 0.0143 (11) |
| C8 | 0.0559 (13) | 0.0450 (12) | 0.0399 (11) | 0.0026 (10) | 0.0093 (10) | 0.0142 (9) |
| C9 | 0.0420 (10) | 0.0360 (10) | 0.0385 (11) | 0.0083 (8) | 0.0094 (8) | 0.0153 (9) |
| C10 | 0.0407 (10) | 0.0347 (10) | 0.0338 (10) | 0.0101 (8) | 0.0086 (8) | 0.0120 (8) |
| C11 | 0.0456 (11) | 0.0430 (11) | 0.0311 (10) | 0.0065 (9) | 0.0098 (8) | 0.0103 (9) |
| C12 | 0.0417 (10) | 0.0397 (11) | 0.0388 (11) | 0.0102 (9) | 0.0131 (9) | 0.0147 (9) |
| C13 | 0.0532 (12) | 0.0554 (13) | 0.0408 (12) | 0.0066 (10) | 0.0190 (10) | 0.0172 (10) |
| C14 | 0.0510 (13) | 0.0619 (15) | 0.0585 (14) | 0.0030 (11) | 0.0239 (11) | 0.0263 (12) |
| C15 | 0.0446 (12) | 0.0515 (13) | 0.0598 (14) | 0.0018 (10) | 0.0106 (10) | 0.0233 (11) |
| C16 | 0.0433 (11) | 0.0431 (12) | 0.0429 (11) | 0.0047 (9) | 0.0054 (9) | 0.0149 (9) |
| C17 | 0.0370 (10) | 0.0360 (10) | 0.0350 (10) | 0.0056 (8) | 0.0092 (8) | 0.0118 (8) |
| C18 | 0.0581 (13) | 0.0569 (14) | 0.0416 (12) | 0.0271 (11) | 0.0119 (10) | 0.0157 (10) |
| C19 | 0.0624 (14) | 0.0656 (15) | 0.0406 (12) | 0.0183 (12) | 0.0021 (11) | 0.0218 (11) |
| C20 | 0.0572 (13) | 0.0432 (12) | 0.0350 (11) | −0.0068 (10) | 0.0102 (10) | 0.0100 (9) |
| C21 | 0.0612 (14) | 0.0553 (14) | 0.0470 (13) | 0.0184 (11) | 0.0196 (11) | 0.0039 (11) |
| C22 | 0.0496 (12) | 0.0575 (14) | 0.0426 (12) | 0.0214 (11) | 0.0069 (10) | 0.0103 (10) |
| C23 | 0.100 (2) | 0.0677 (17) | 0.0405 (13) | −0.0129 (15) | 0.0131 (13) | 0.0077 (12) |
| S1 | 0.0469 (3) | 0.0525 (3) | 0.0360 (3) | 0.0051 (2) | 0.0137 (2) | 0.0165 (2) |
(I) 6-(p-Tolyl)benzo[b]naphtho[2,3-d]thiophene . Geometric parameters (Å, º)
| C1—C16 | 1.411 (3) | C12—C13 | 1.420 (3) |
| C1—C2 | 1.426 (3) | C13—C14 | 1.349 (3) |
| C1—C12 | 1.434 (3) | C13—H13 | 0.9300 |
| C2—C3 | 1.373 (3) | C14—C15 | 1.405 (3) |
| C2—C17 | 1.492 (3) | C14—H14 | 0.9300 |
| C3—C10 | 1.423 (3) | C15—C16 | 1.358 (3) |
| C3—S1 | 1.7492 (19) | C15—H15 | 0.9300 |
| C4—C5 | 1.384 (3) | C16—H16 | 0.9300 |
| C4—C9 | 1.397 (3) | C17—C18 | 1.375 (3) |
| C4—S1 | 1.746 (2) | C17—C22 | 1.376 (3) |
| C5—C6 | 1.372 (3) | C18—C19 | 1.377 (3) |
| C5—H5 | 0.9300 | C18—H18 | 0.9300 |
| C6—C7 | 1.388 (3) | C19—C20 | 1.370 (3) |
| C6—H6 | 0.9300 | C19—H19 | 0.9300 |
| C7—C8 | 1.373 (3) | C20—C21 | 1.366 (3) |
| C7—H7 | 0.9300 | C20—C23 | 1.508 (3) |
| C8—C9 | 1.393 (3) | C21—C22 | 1.382 (3) |
| C8—H8 | 0.9300 | C21—H21 | 0.9300 |
| C9—C10 | 1.449 (3) | C22—H22 | 0.9300 |
| C10—C11 | 1.369 (3) | C23—H23A | 0.9600 |
| C11—C12 | 1.400 (3) | C23—H23B | 0.9600 |
| C11—H11 | 0.9300 | C23—H23C | 0.9600 |
| C16—C1—C2 | 122.80 (18) | C14—C13—H13 | 119.2 |
| C16—C1—C12 | 117.81 (17) | C12—C13—H13 | 119.2 |
| C2—C1—C12 | 119.39 (17) | C13—C14—C15 | 120.2 (2) |
| C3—C2—C1 | 117.87 (17) | C13—C14—H14 | 119.9 |
| C3—C2—C17 | 120.13 (17) | C15—C14—H14 | 119.9 |
| C1—C2—C17 | 121.99 (17) | C16—C15—C14 | 120.2 (2) |
| C2—C3—C10 | 123.09 (17) | C16—C15—H15 | 119.9 |
| C2—C3—S1 | 125.07 (15) | C14—C15—H15 | 119.9 |
| C10—C3—S1 | 111.84 (14) | C15—C16—C1 | 121.9 (2) |
| C5—C4—C9 | 121.40 (19) | C15—C16—H16 | 119.1 |
| C5—C4—S1 | 125.91 (16) | C1—C16—H16 | 119.1 |
| C9—C4—S1 | 112.68 (15) | C18—C17—C22 | 117.15 (19) |
| C6—C5—C4 | 118.5 (2) | C18—C17—C2 | 122.18 (17) |
| C6—C5—H5 | 120.8 | C22—C17—C2 | 120.65 (17) |
| C4—C5—H5 | 120.8 | C17—C18—C19 | 121.4 (2) |
| C5—C6—C7 | 121.0 (2) | C17—C18—H18 | 119.3 |
| C5—C6—H6 | 119.5 | C19—C18—H18 | 119.3 |
| C7—C6—H6 | 119.5 | C20—C19—C18 | 121.4 (2) |
| C8—C7—C6 | 120.6 (2) | C20—C19—H19 | 119.3 |
| C8—C7—H7 | 119.7 | C18—C19—H19 | 119.3 |
| C6—C7—H7 | 119.7 | C21—C20—C19 | 117.3 (2) |
| C7—C8—C9 | 119.6 (2) | C21—C20—C23 | 121.5 (2) |
| C7—C8—H8 | 120.2 | C19—C20—C23 | 121.2 (2) |
| C9—C8—H8 | 120.2 | C20—C21—C22 | 121.7 (2) |
| C8—C9—C4 | 118.95 (19) | C20—C21—H21 | 119.1 |
| C8—C9—C10 | 128.82 (18) | C22—C21—H21 | 119.1 |
| C4—C9—C10 | 112.23 (17) | C17—C22—C21 | 121.0 (2) |
| C11—C10—C3 | 118.90 (18) | C17—C22—H22 | 119.5 |
| C11—C10—C9 | 129.40 (18) | C21—C22—H22 | 119.5 |
| C3—C10—C9 | 111.69 (17) | C20—C23—H23A | 109.5 |
| C10—C11—C12 | 120.75 (18) | C20—C23—H23B | 109.5 |
| C10—C11—H11 | 119.6 | H23A—C23—H23B | 109.5 |
| C12—C11—H11 | 119.6 | C20—C23—H23C | 109.5 |
| C11—C12—C13 | 121.63 (19) | H23A—C23—H23C | 109.5 |
| C11—C12—C1 | 120.00 (17) | H23B—C23—H23C | 109.5 |
| C13—C12—C1 | 118.37 (18) | C4—S1—C3 | 91.52 (9) |
| C14—C13—C12 | 121.6 (2) | ||
| C16—C1—C2—C3 | −179.76 (17) | C10—C11—C12—C1 | −0.5 (3) |
| C12—C1—C2—C3 | −0.2 (3) | C16—C1—C12—C11 | −179.63 (17) |
| C16—C1—C2—C17 | −0.5 (3) | C2—C1—C12—C11 | 0.8 (3) |
| C12—C1—C2—C17 | 179.12 (16) | C16—C1—C12—C13 | 0.1 (3) |
| C1—C2—C3—C10 | −0.6 (3) | C2—C1—C12—C13 | −179.48 (18) |
| C17—C2—C3—C10 | −179.96 (16) | C11—C12—C13—C14 | 179.1 (2) |
| C1—C2—C3—S1 | 179.27 (13) | C1—C12—C13—C14 | −0.6 (3) |
| C17—C2—C3—S1 | −0.1 (3) | C12—C13—C14—C15 | 0.6 (4) |
| C9—C4—C5—C6 | −1.3 (3) | C13—C14—C15—C16 | −0.1 (3) |
| S1—C4—C5—C6 | 179.61 (17) | C14—C15—C16—C1 | −0.4 (3) |
| C4—C5—C6—C7 | −0.3 (3) | C2—C1—C16—C15 | 179.98 (18) |
| C5—C6—C7—C8 | 1.3 (4) | C12—C1—C16—C15 | 0.4 (3) |
| C6—C7—C8—C9 | −0.7 (3) | C3—C2—C17—C18 | −108.5 (2) |
| C7—C8—C9—C4 | −0.9 (3) | C1—C2—C17—C18 | 72.2 (3) |
| C7—C8—C9—C10 | 178.1 (2) | C3—C2—C17—C22 | 70.1 (3) |
| C5—C4—C9—C8 | 1.9 (3) | C1—C2—C17—C22 | −109.1 (2) |
| S1—C4—C9—C8 | −178.87 (15) | C22—C17—C18—C19 | −0.7 (3) |
| C5—C4—C9—C10 | −177.24 (18) | C2—C17—C18—C19 | 177.9 (2) |
| S1—C4—C9—C10 | 2.0 (2) | C17—C18—C19—C20 | 0.3 (4) |
| C2—C3—C10—C11 | 0.9 (3) | C18—C19—C20—C21 | 0.4 (4) |
| S1—C3—C10—C11 | −179.04 (15) | C18—C19—C20—C23 | −179.5 (2) |
| C2—C3—C10—C9 | 179.87 (17) | C19—C20—C21—C22 | −0.6 (4) |
| S1—C3—C10—C9 | 0.0 (2) | C23—C20—C21—C22 | 179.3 (2) |
| C8—C9—C10—C11 | −1.4 (3) | C18—C17—C22—C21 | 0.5 (3) |
| C4—C9—C10—C11 | 177.64 (19) | C2—C17—C22—C21 | −178.2 (2) |
| C8—C9—C10—C3 | 179.71 (19) | C20—C21—C22—C17 | 0.2 (4) |
| C4—C9—C10—C3 | −1.2 (2) | C5—C4—S1—C3 | 177.47 (19) |
| C3—C10—C11—C12 | −0.3 (3) | C9—C4—S1—C3 | −1.69 (15) |
| C9—C10—C11—C12 | −179.05 (18) | C2—C3—S1—C4 | −178.95 (17) |
| C10—C11—C12—C13 | 179.71 (18) | C10—C3—S1—C4 | 0.96 (14) |
(I) 6-(p-Tolyl)benzo[b]naphtho[2,3-d]thiophene . Hydrogen-bond geometry (Å, º)
Cg3, Cg4 and Cg5 are the centroids of rings (C1/C12–C16), (C4–C6) and (C17–C22), respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C15—H15···Cg5i | 0.93 | 2.94 | 3.763 (3) | 148 |
| C19—H19···Cg4ii | 0.93 | 2.94 | 3.753 (3) | 147 |
| C21—H21···Cg3iii | 0.93 | 2.91 | 3.721 (3) | 146 |
Symmetry codes: (i) −x−1, −y, −z; (ii) −x, −y+1, −z; (iii) −x, −y, −z.
(II) 7-Phenylanthra[2,3-b]benzo[d]thiophene . Crystal data
| C26H16S | F(000) = 1504 |
| Mr = 360.45 | Dx = 1.330 Mg m−3 |
| Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ab 2ac | Cell parameters from 3171 reflections |
| a = 12.2159 (8) Å | θ = 2.5–25.0° |
| b = 33.1138 (4) Å | µ = 0.19 mm−1 |
| c = 8.8993 (5) Å | T = 296 K |
| V = 3599.9 (3) Å3 | Block, colourless |
| Z = 8 | 0.30 × 0.25 × 0.25 mm |
(II) 7-Phenylanthra[2,3-b]benzo[d]thiophene . Data collection
| Bruker Kappa APEXII CCD diffractometer | 3171 independent reflections |
| Radiation source: fine-focus sealed tube | 2540 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.036 |
| ω & φ scans | θmax = 25.0°, θmin = 2.5° |
| Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −14→14 |
| Tmin = 0.946, Tmax = 0.955 | k = −39→39 |
| 43542 measured reflections | l = −10→9 |
(II) 7-Phenylanthra[2,3-b]benzo[d]thiophene . Refinement
| 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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.182 | H-atom parameters constrained |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0831P)2 + 5.3659P] where P = (Fo2 + 2Fc2)/3 |
| 3171 reflections | (Δ/σ)max < 0.001 |
| 244 parameters | Δρmax = 1.06 e Å−3 |
| 0 restraints | Δρmin = −0.40 e Å−3 |
(II) 7-Phenylanthra[2,3-b]benzo[d]thiophene . Special details
| 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. |
(II) 7-Phenylanthra[2,3-b]benzo[d]thiophene . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.4387 (2) | 0.40078 (9) | 0.4515 (3) | 0.0366 (7) | |
| C2 | 0.4905 (3) | 0.42302 (9) | 0.3361 (3) | 0.0412 (7) | |
| H2 | 0.5423 | 0.4107 | 0.2749 | 0.049* | |
| C3 | 0.4643 (3) | 0.46257 (9) | 0.3144 (3) | 0.0422 (7) | |
| C4 | 0.4365 (3) | 0.53427 (10) | 0.2336 (4) | 0.0494 (8) | |
| C5 | 0.4359 (3) | 0.57228 (11) | 0.1701 (4) | 0.0581 (9) | |
| H5 | 0.4836 | 0.5788 | 0.0923 | 0.070* | |
| C6 | 0.3634 (4) | 0.60010 (11) | 0.2244 (5) | 0.0667 (11) | |
| H6 | 0.3614 | 0.6257 | 0.1819 | 0.080* | |
| C7 | 0.2930 (3) | 0.59091 (11) | 0.3413 (5) | 0.0626 (11) | |
| H7 | 0.2442 | 0.6103 | 0.3762 | 0.075* | |
| C8 | 0.2948 (3) | 0.55284 (10) | 0.4065 (4) | 0.0532 (9) | |
| H8 | 0.2479 | 0.5466 | 0.4855 | 0.064* | |
| C9 | 0.3679 (3) | 0.52414 (9) | 0.3515 (4) | 0.0454 (8) | |
| C10 | 0.3829 (3) | 0.48249 (9) | 0.4034 (4) | 0.0416 (7) | |
| C11 | 0.3348 (3) | 0.46241 (9) | 0.5176 (4) | 0.0442 (8) | |
| H11 | 0.2827 | 0.4754 | 0.5764 | 0.053* | |
| C12 | 0.3627 (2) | 0.42151 (9) | 0.5490 (4) | 0.0400 (7) | |
| C13 | 0.3191 (3) | 0.40108 (10) | 0.6711 (4) | 0.0432 (7) | |
| H13 | 0.2707 | 0.4145 | 0.7344 | 0.052* | |
| C14 | 0.3452 (2) | 0.36119 (9) | 0.7016 (3) | 0.0402 (7) | |
| C15 | 0.3034 (3) | 0.34053 (11) | 0.8295 (4) | 0.0492 (8) | |
| H15 | 0.2612 | 0.3547 | 0.8986 | 0.059* | |
| C16 | 0.3231 (3) | 0.30128 (11) | 0.8533 (4) | 0.0548 (9) | |
| H16 | 0.2945 | 0.2886 | 0.9379 | 0.066* | |
| C17 | 0.3869 (3) | 0.27908 (11) | 0.7506 (4) | 0.0557 (9) | |
| H17 | 0.3987 | 0.2517 | 0.7666 | 0.067* | |
| C18 | 0.4313 (3) | 0.29732 (10) | 0.6286 (4) | 0.0464 (8) | |
| H18 | 0.4737 | 0.2822 | 0.5626 | 0.056* | |
| C19 | 0.4146 (2) | 0.33940 (9) | 0.5989 (3) | 0.0379 (7) | |
| C20 | 0.4605 (2) | 0.35934 (9) | 0.4753 (3) | 0.0359 (7) | |
| C21 | 0.5279 (2) | 0.33716 (8) | 0.3628 (3) | 0.0362 (7) | |
| C22 | 0.6302 (3) | 0.32209 (9) | 0.3981 (4) | 0.0466 (8) | |
| H22 | 0.6588 | 0.3261 | 0.4938 | 0.056* | |
| C23 | 0.6905 (3) | 0.30109 (10) | 0.2926 (4) | 0.0538 (9) | |
| H23 | 0.7593 | 0.2912 | 0.3180 | 0.065* | |
| C24 | 0.6502 (3) | 0.29467 (10) | 0.1514 (4) | 0.0530 (9) | |
| H24 | 0.6904 | 0.2799 | 0.0817 | 0.064* | |
| C25 | 0.5496 (3) | 0.31020 (11) | 0.1135 (4) | 0.0534 (9) | |
| H25 | 0.5224 | 0.3064 | 0.0169 | 0.064* | |
| C26 | 0.4887 (3) | 0.33134 (10) | 0.2176 (4) | 0.0478 (8) | |
| H26 | 0.4208 | 0.3418 | 0.1905 | 0.057* | |
| S1 | 0.52265 (8) | 0.49395 (3) | 0.18065 (10) | 0.0547 (3) |
(II) 7-Phenylanthra[2,3-b]benzo[d]thiophene . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0346 (15) | 0.0381 (15) | 0.0371 (15) | 0.0019 (12) | −0.0045 (13) | −0.0064 (13) |
| C2 | 0.0445 (17) | 0.0402 (16) | 0.0391 (17) | 0.0081 (13) | −0.0050 (14) | −0.0058 (13) |
| C3 | 0.0466 (18) | 0.0413 (17) | 0.0388 (17) | 0.0005 (14) | −0.0070 (14) | −0.0041 (13) |
| C4 | 0.0527 (19) | 0.0462 (18) | 0.0492 (19) | 0.0015 (15) | −0.0137 (17) | −0.0067 (15) |
| C5 | 0.063 (2) | 0.055 (2) | 0.056 (2) | −0.0056 (18) | −0.0142 (18) | 0.0020 (17) |
| C6 | 0.079 (3) | 0.0383 (19) | 0.083 (3) | −0.0056 (18) | −0.031 (2) | 0.0072 (19) |
| C7 | 0.057 (2) | 0.0421 (19) | 0.089 (3) | 0.0117 (16) | −0.016 (2) | −0.0154 (19) |
| C8 | 0.0470 (19) | 0.0497 (19) | 0.063 (2) | −0.0002 (15) | −0.0075 (16) | −0.0095 (17) |
| C9 | 0.0474 (18) | 0.0382 (16) | 0.0506 (19) | 0.0015 (14) | −0.0136 (15) | −0.0088 (14) |
| C10 | 0.0424 (16) | 0.0400 (16) | 0.0425 (17) | 0.0043 (13) | −0.0097 (14) | −0.0108 (14) |
| C11 | 0.0428 (17) | 0.0422 (16) | 0.0477 (19) | 0.0079 (14) | −0.0018 (15) | −0.0117 (14) |
| C12 | 0.0371 (15) | 0.0397 (16) | 0.0431 (17) | 0.0068 (12) | −0.0045 (13) | −0.0131 (13) |
| C13 | 0.0381 (16) | 0.0488 (18) | 0.0429 (17) | 0.0036 (13) | 0.0049 (14) | −0.0106 (14) |
| C14 | 0.0320 (15) | 0.0461 (17) | 0.0424 (17) | 0.0001 (13) | −0.0032 (13) | −0.0085 (14) |
| C15 | 0.0404 (17) | 0.064 (2) | 0.0436 (18) | −0.0002 (15) | 0.0069 (15) | −0.0034 (16) |
| C16 | 0.056 (2) | 0.060 (2) | 0.048 (2) | −0.0037 (17) | 0.0068 (17) | 0.0067 (17) |
| C17 | 0.063 (2) | 0.0480 (19) | 0.056 (2) | −0.0015 (16) | 0.0022 (18) | 0.0074 (17) |
| C18 | 0.0499 (19) | 0.0428 (17) | 0.0463 (18) | 0.0039 (14) | 0.0009 (15) | −0.0041 (14) |
| C19 | 0.0346 (15) | 0.0414 (16) | 0.0378 (16) | 0.0013 (12) | −0.0052 (13) | −0.0063 (13) |
| C20 | 0.0337 (14) | 0.0350 (14) | 0.0390 (16) | 0.0047 (12) | −0.0053 (12) | −0.0070 (12) |
| C21 | 0.0395 (16) | 0.0313 (14) | 0.0378 (16) | 0.0015 (12) | −0.0001 (13) | −0.0026 (12) |
| C22 | 0.0503 (19) | 0.0420 (17) | 0.0473 (19) | 0.0103 (14) | −0.0043 (15) | −0.0079 (14) |
| C23 | 0.0486 (19) | 0.0469 (18) | 0.066 (2) | 0.0118 (15) | 0.0052 (17) | −0.0024 (17) |
| C24 | 0.058 (2) | 0.0461 (18) | 0.055 (2) | 0.0043 (16) | 0.0195 (18) | −0.0078 (16) |
| C25 | 0.062 (2) | 0.058 (2) | 0.0407 (18) | −0.0048 (17) | 0.0045 (16) | −0.0088 (16) |
| C26 | 0.0431 (17) | 0.055 (2) | 0.0450 (18) | 0.0027 (15) | 0.0013 (15) | −0.0070 (15) |
| S1 | 0.0709 (6) | 0.0480 (5) | 0.0453 (5) | 0.0081 (4) | 0.0074 (4) | 0.0035 (4) |
(II) 7-Phenylanthra[2,3-b]benzo[d]thiophene . Geometric parameters (Å, º)
| C1—C20 | 1.414 (4) | C13—H13 | 0.9300 |
| C1—C2 | 1.414 (4) | C14—C15 | 1.423 (5) |
| C1—C12 | 1.444 (4) | C14—C19 | 1.440 (4) |
| C2—C3 | 1.362 (4) | C15—C16 | 1.338 (5) |
| C2—H2 | 0.9300 | C15—H15 | 0.9300 |
| C3—C10 | 1.431 (4) | C16—C17 | 1.408 (5) |
| C3—S1 | 1.734 (3) | C16—H16 | 0.9300 |
| C4—C5 | 1.380 (5) | C17—C18 | 1.356 (5) |
| C4—C9 | 1.385 (5) | C17—H17 | 0.9300 |
| C4—S1 | 1.764 (4) | C18—C19 | 1.433 (4) |
| C5—C6 | 1.366 (6) | C18—H18 | 0.9300 |
| C5—H5 | 0.9300 | C19—C20 | 1.400 (4) |
| C6—C7 | 1.384 (6) | C20—C21 | 1.489 (4) |
| C6—H6 | 0.9300 | C21—C22 | 1.382 (4) |
| C7—C8 | 1.388 (5) | C21—C26 | 1.392 (4) |
| C7—H7 | 0.9300 | C22—C23 | 1.381 (5) |
| C8—C9 | 1.393 (5) | C22—H22 | 0.9300 |
| C8—H8 | 0.9300 | C23—C24 | 1.366 (5) |
| C9—C10 | 1.466 (4) | C23—H23 | 0.9300 |
| C10—C11 | 1.350 (5) | C24—C25 | 1.374 (5) |
| C11—C12 | 1.424 (4) | C24—H24 | 0.9300 |
| C11—H11 | 0.9300 | C25—C26 | 1.380 (5) |
| C12—C13 | 1.386 (5) | C25—H25 | 0.9300 |
| C13—C14 | 1.386 (4) | C26—H26 | 0.9300 |
| C20—C1—C2 | 122.0 (3) | C13—C14—C19 | 119.2 (3) |
| C20—C1—C12 | 119.5 (3) | C15—C14—C19 | 118.6 (3) |
| C2—C1—C12 | 118.5 (3) | C16—C15—C14 | 121.9 (3) |
| C3—C2—C1 | 119.9 (3) | C16—C15—H15 | 119.0 |
| C3—C2—H2 | 120.1 | C14—C15—H15 | 119.0 |
| C1—C2—H2 | 120.1 | C15—C16—C17 | 120.2 (3) |
| C2—C3—C10 | 121.9 (3) | C15—C16—H16 | 119.9 |
| C2—C3—S1 | 125.2 (3) | C17—C16—H16 | 119.9 |
| C10—C3—S1 | 112.9 (2) | C18—C17—C16 | 120.6 (3) |
| C5—C4—C9 | 121.9 (3) | C18—C17—H17 | 119.7 |
| C5—C4—S1 | 125.7 (3) | C16—C17—H17 | 119.7 |
| C9—C4—S1 | 112.3 (3) | C17—C18—C19 | 121.6 (3) |
| C6—C5—C4 | 118.3 (4) | C17—C18—H18 | 119.2 |
| C6—C5—H5 | 120.9 | C19—C18—H18 | 119.2 |
| C4—C5—H5 | 120.9 | C20—C19—C18 | 123.1 (3) |
| C5—C6—C7 | 121.4 (3) | C20—C19—C14 | 119.9 (3) |
| C5—C6—H6 | 119.3 | C18—C19—C14 | 117.0 (3) |
| C7—C6—H6 | 119.3 | C19—C20—C1 | 120.0 (3) |
| C6—C7—C8 | 120.3 (3) | C19—C20—C21 | 121.1 (3) |
| C6—C7—H7 | 119.9 | C1—C20—C21 | 118.8 (3) |
| C8—C7—H7 | 119.9 | C22—C21—C26 | 118.2 (3) |
| C7—C8—C9 | 118.9 (4) | C22—C21—C20 | 121.7 (3) |
| C7—C8—H8 | 120.6 | C26—C21—C20 | 120.1 (3) |
| C9—C8—H8 | 120.6 | C23—C22—C21 | 120.6 (3) |
| C8—C9—C4 | 119.3 (3) | C23—C22—H22 | 119.7 |
| C8—C9—C10 | 127.7 (3) | C21—C22—H22 | 119.7 |
| C4—C9—C10 | 113.0 (3) | C22—C23—C24 | 120.8 (3) |
| C11—C10—C3 | 119.5 (3) | C22—C23—H23 | 119.6 |
| C11—C10—C9 | 130.2 (3) | C24—C23—H23 | 119.6 |
| C3—C10—C9 | 110.3 (3) | C25—C24—C23 | 119.3 (3) |
| C10—C11—C12 | 120.8 (3) | C25—C24—H24 | 120.3 |
| C10—C11—H11 | 119.6 | C23—C24—H24 | 120.3 |
| C12—C11—H11 | 119.6 | C24—C25—C26 | 120.5 (3) |
| C13—C12—C11 | 121.7 (3) | C24—C25—H25 | 119.8 |
| C13—C12—C1 | 119.1 (3) | C26—C25—H25 | 119.8 |
| C11—C12—C1 | 119.2 (3) | C25—C26—C21 | 120.5 (3) |
| C12—C13—C14 | 122.0 (3) | C25—C26—H26 | 119.7 |
| C12—C13—H13 | 119.0 | C21—C26—H26 | 119.7 |
| C14—C13—H13 | 119.0 | C3—S1—C4 | 91.43 (16) |
| C13—C14—C15 | 122.2 (3) | ||
| C20—C1—C2—C3 | 177.9 (3) | C13—C14—C15—C16 | 175.5 (3) |
| C12—C1—C2—C3 | −3.1 (4) | C19—C14—C15—C16 | −2.7 (5) |
| C1—C2—C3—C10 | −1.6 (5) | C14—C15—C16—C17 | 0.1 (5) |
| C1—C2—C3—S1 | 178.5 (2) | C15—C16—C17—C18 | 1.6 (6) |
| C9—C4—C5—C6 | −1.4 (5) | C16—C17—C18—C19 | −0.5 (5) |
| S1—C4—C5—C6 | 179.9 (3) | C17—C18—C19—C20 | 179.0 (3) |
| C4—C5—C6—C7 | 0.8 (6) | C17—C18—C19—C14 | −2.1 (5) |
| C5—C6—C7—C8 | 0.1 (6) | C13—C14—C19—C20 | 4.3 (4) |
| C6—C7—C8—C9 | −0.5 (5) | C15—C14—C19—C20 | −177.5 (3) |
| C7—C8—C9—C4 | −0.1 (5) | C13—C14—C19—C18 | −174.7 (3) |
| C7—C8—C9—C10 | −179.9 (3) | C15—C14—C19—C18 | 3.6 (4) |
| C5—C4—C9—C8 | 1.1 (5) | C18—C19—C20—C1 | 178.8 (3) |
| S1—C4—C9—C8 | 180.0 (2) | C14—C19—C20—C1 | −0.1 (4) |
| C5—C4—C9—C10 | −179.2 (3) | C18—C19—C20—C21 | 2.0 (4) |
| S1—C4—C9—C10 | −0.2 (3) | C14—C19—C20—C21 | −176.9 (3) |
| C2—C3—C10—C11 | 3.8 (5) | C2—C1—C20—C19 | 174.5 (3) |
| S1—C3—C10—C11 | −176.4 (2) | C12—C1—C20—C19 | −4.5 (4) |
| C2—C3—C10—C9 | −177.4 (3) | C2—C1—C20—C21 | −8.6 (4) |
| S1—C3—C10—C9 | 2.5 (3) | C12—C1—C20—C21 | 172.4 (3) |
| C8—C9—C10—C11 | −3.0 (6) | C19—C20—C21—C22 | −69.3 (4) |
| C4—C9—C10—C11 | 177.3 (3) | C1—C20—C21—C22 | 113.8 (3) |
| C8—C9—C10—C3 | 178.4 (3) | C19—C20—C21—C26 | 111.1 (3) |
| C4—C9—C10—C3 | −1.4 (4) | C1—C20—C21—C26 | −65.7 (4) |
| C3—C10—C11—C12 | −1.0 (5) | C26—C21—C22—C23 | −1.4 (5) |
| C9—C10—C11—C12 | −179.6 (3) | C20—C21—C22—C23 | 179.0 (3) |
| C10—C11—C12—C13 | 176.1 (3) | C21—C22—C23—C24 | −0.2 (5) |
| C10—C11—C12—C1 | −3.7 (4) | C22—C23—C24—C25 | 1.6 (5) |
| C20—C1—C12—C13 | 4.9 (4) | C23—C24—C25—C26 | −1.4 (5) |
| C2—C1—C12—C13 | −174.1 (3) | C24—C25—C26—C21 | −0.2 (5) |
| C20—C1—C12—C11 | −175.3 (3) | C22—C21—C26—C25 | 1.6 (5) |
| C2—C1—C12—C11 | 5.7 (4) | C20—C21—C26—C25 | −178.8 (3) |
| C11—C12—C13—C14 | 179.5 (3) | C2—C3—S1—C4 | 177.6 (3) |
| C1—C12—C13—C14 | −0.7 (5) | C10—C3—S1—C4 | −2.2 (2) |
| C12—C13—C14—C15 | 177.9 (3) | C5—C4—S1—C3 | −179.7 (3) |
| C12—C13—C14—C19 | −3.9 (5) | C9—C4—S1—C3 | 1.4 (3) |
(II) 7-Phenylanthra[2,3-b]benzo[d]thiophene . Hydrogen-bond geometry (Å, º)
Cg2 and Cg3 are the centroids of rings (C1–C3/C10–C12) and (C1/C12–C14/C19/C20), respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C13—H13···Cg2i | 0.93 | 2.97 | 3.885 (4) | 168 |
| C15—H15···Cg3i | 0.93 | 2.57 | 3.479 (4) | 166 |
Symmetry code: (i) x, −y−1/2, z−1/2.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, II, global. DOI: 10.1107/S2056989016012937/lh5819sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016012937/lh5819Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989016012937/lh5819IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989016012937/lh5819Isup4.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report