The crystal structures of two benzothiophene derivatives are described along with an analysis of the intermolecular contacts in the crystals performed using Hirshfeld surface analysis and two-dimensional fingerprint plots.
Keywords: crystal structure, thiophene, benzothiophene, dihydrobenzene, dihydropyridine 5-(phenylsulfonyl), 12-(phenylsulfonyl), phenanthridine hydrogen bonding, Hirshfeld surface analysis.
Abstract
In both of the title compounds, C26H19NO2S2, (I), and C25H19NO2S2, (II), the benzothiophene rings are essentially planar with maximum deviations of 0.026 (1) and −0.016 (1) Å for the carbon and sulfur atoms in compounds (I) and (II), respectively. In (I), the thiophene ring system is almost orthogonal to the phenyl ring attached to the sulfonyl group, subtending a dihedral angle of 88.1 (1)°, and the dihydropyridine ring adopts a screw–boat conformation. In both compounds, the molecular structure is consolidated by weak C—H⋯O intramolecular interactions formed by the sulfone oxygen atoms, which generate S(5) ring motifs. In the crystal of II, molecules are linked via C—H⋯O hydrogen bonds, generating C(7) chains running along the [100] direction. No significant intermolecular interactions are observed in I.
1. Chemical context
Thiophene, C4H4S, belongs to a class of aromatic five-membered heterocycles comprising one S heteroatom. Thiophene derivatives possess pharmacological and biological activities including antibacterial (Mishra et al., 2012 ▸), antiallergic (Gillespie et al.,1985 ▸), anti-cancer and anti-toxic (Gewald et al., 1966 ▸), analgesic (Laddi et al., 1998 ▸; Chen et al., 2008 ▸), anti-inflammatory (Ferreira et al., 2006 ▸), antioxidant (Jarak et al., 2005 ▸), antitumor (Gadad et al., 1994 ▸), antimicrobial (Abdel-Rahman et al., 2003 ▸), antihypertensive (Monge Vega et al., 1980 ▸), anti-diabetes mellitus (Abdelhamid et al., 2009 ▸), gonadotropin releasing hormone antagonist (Sabins et al., 1944 ▸) and are building blocks in many agrochemicals (Ansary & Omar, 2001 ▸). Thiophene possesses promising pharmacological activities, such as anti-HIV PR inhibitor (Bonini et al., 2005 ▸) and anti-breast cancer (Brault et al., 2005 ▸). Benzothiophenes are biologically energetic molecules. One of the most significant drugs based on the benzothiophene structure is Raloxifine, used for the stoppage and cure of osteoporosis in postmenopausal women (Jordan, 2003 ▸). Benzothiophenes are also present in luminescent components used in organic materials (Russell & Press, 1996 ▸). Thiophene derivatives have a wide variety of applications in optical and electronic systems (Gather et al., 2008 ▸; He et al., 2009 ▸) and are used extensively in solar cells (Justin Thomas et al., 2008 ▸), 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 ▸). Thieno-pyridine products are used in medicine as allosteric adenosine receptors and in the treatment of adenosine-sensitive cardiac arrhythmias (Tumey et al., 2008 ▸; Grunewald et al., 2008 ▸). Herein we report the crystal structure and Hirshfeld surface analysis of the title thiophene derivatives.
2. Structural commentary
The molecular structure of compound I (Fig. 1 ▸) comprises a benzothiophene ring system (S1/C1–C8) attached to a 4-methyl 5-(phenylsulfonyl)-5,6-dihydrophenanthridine unit (C7–C26/N1/S2/O1/O2), while compound II comprises a benzothiophene ring system (S1/C1–C8) attached to an N-(2-allylphenyl)-N-prop-2-yn-1-yl benzenesulfonamide group (C9–C15/N1/S2/O1/O2) (Fig. 2 ▸). In both compounds, the benzothiophene ring system (S1/C1–C8) is essentially planar with maximum deviations of 0.026 (1) and 0.016 (1) Å for atom C6 and S1 in compounds I and II, respectively. The mean planes of the thiophene ring systems make dihedral angles of 2.1 (1), 19.0 (1) and 33.9 (1), respectively, in compound I and 0.7 (2), 38.1 (2) and 87.6 (2)°, respectively, in compound II with the C1–C6, C11–C16 and C17–C22 phenyl rings. The benzothiophene ring system is almost orthogonal to the C17–C22 phenyl ring attached to the sulfonyl group in I, subtending a dihedral angle of 88.1 (1)°, while the dihydropyridine ring (C10/C11/C16/C23/C24) adopts a screw–boat conformation, as is evident from the Cremer–Pople puckering analysis of the six-membered heterocyclic ring [Q = 0.4451 (13) Å, θ = 111.5 (2) and φ = 146.9 (2)°]
Figure 1.
The molecular structure of compound I, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Intramolecular contacts are shown as dashed lines (Table 1 ▸).
Figure 2.
The molecular structure of compound II, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Intramolecular contacts are shown as dashed lines (Table 2 ▸).
In both compounds, the tetrahedral configuration is distorted around the atom S2. The increase in the O2—S2—O1 angle [120.0 (1)° in I and 119.9 (2)° in II], with a simultaneous decrease in the N1—S2—C17 angle [108.5 (1)° in I and 107.6 (1)° in II] from the ideal tetrahedral value (109.5°) are attributed to the Thorpe–Ingold effect (Bassindale, 1984 ▸). The widening of the angles may be due to the repulsive interaction between the two short S=O bonds. The N1—C23 [1.477 (2) Å in I and 1.477 (3) Å in II] and N1—C16 [1.433 (2) Å in I and 1.444 (3) Å in (II] bond lengths in the molecule are longer than the mean Nsp 2—Csp 2 bond length value of 1.355 (14) Å (Allen et al., 1987 ▸; Cambridge Structural Database (CSD) Version 5.37; Groom et al., 2016 ▸). The elongation observed may be due to the electron-withdrawing character of the phenylsulfonyl group. The sum of the bond angles around N1 [350.2° in I and 357.6° in II]] indicate the sp 2 hybridization. The geometric parameters of compounds I and II agree well with those reported for related structures (Madhan et al., 2022 ▸).
In both compounds, the molecular structure is stabilized by weak C23—H23⋯O1 intramolecular interactions (Tables 1 ▸ and 2 ▸) formed by the sulfone oxygen atoms, which generate S(5) ring motifs (Figs. 1 ▸ and 2 ▸).
Table 1. Hydrogen-bond geometry (Å, °) for I .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C23—H23A⋯O1 | 0.97 | 2.41 | 2.8935 (17) | 111 |
Table 2. Hydrogen-bond geometry (Å, °) for II .
Cg1 is the centroid of the C1–C6 ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C23—H23A⋯O1 | 0.97 | 2.35 | 2.860 (3) | 112 |
| C25—H25⋯O2i | 0.93 | 2.38 | 3.285 (4) | 166 |
| C21—H21⋯Cg1ii | 0.93 | 2.97 | 3.772 (2) | 139 |
Symmetry codes: (i)
; (ii)
.
3. Supramolecular features
In the crystal of I, weak π–π interactions are present [Cg1⋯Cg2i = 3.766 (2) Å where Cg1 and Cg2 are the centroids of rings S1/C1/C6–C8 and C7–C10/C24/C25, respectively; symmetry code: (i) 1 - x, 1 - y, 1 - z]. No significant intermolecular interactions or C—H⋯π interactions with centroid distances of less than 4 Å are observed in the structure.
In the crystal of II, molecules are linked via C25—H25⋯O1 hydrogen bonding, generating C(7) chains (Bernstein et al., 1995 ▸) running along the [100] direction. Weak π–π [Cg3⋯Cg3ii = 3.649 (2) Å where Cg3 is the centroid of the S1/C1/C6–C8 ring; symmetry code: (ii) −x, 2 − y, 1 − z] and C—H⋯π interactions [C21—H21⋯Cg4iii where Cg4 is the centroid of the C1—C6 ring; symmetry code: (iii) 1 − x, 1 − y, 1 − z]. are also present. Packing view of the title compound are shown in Figs. 3 ▸ and 4 ▸.
Figure 3.
A view along the b-axis of the crystal packing of compound I. The hydrogen bonds are shown as dashed lines (Table 1 ▸), and H atoms not involved in hydrogen bonding have been omitted.
Figure 4.
A view along the a-axis of the crystal packing of compound II. The hydrogen bonds are shown as dashed lines (Table 2 ▸), and H atoms not involved in hydrogen bonding have been omitted.
4. Hirshfeld surface analysis
A recent article by Tiekink and collaborators (Tan et al., 2019 ▸) reviews and describes the uses and utility of Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ▸) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007 ▸) to analyse intermolecular contacts in crystals. The various calculations (d norm, curvedness and shape index and 2D fingerprint plots) were performed with CrystalExplorer17 (Turner et al., 2017 ▸).
The Hirshfeld surfaces of compounds I and II mapped over d norm are shown in Fig. 5 ▸. They are colour-mapped with the normalized contact distance, d norm, from red (distances shorter than the sum of the van der Waals radii) through white to blue (distances longer than the sum of the van der Waals radii). The d norm surface was mapped over a fixed colour scale of −0.085 (red) to 1.564 (blue) for compound I and −0.286 (red) to 1.374 (blue) for compound II. The red spots indicate intermolecular contacts involved in hydrogen bonding.
Figure 5.
The Hirshfeld surfaces of compounds I and II, mapped over d norm
The fingerprint plots are illustrated in Figs. 6 ▸ and 7 ▸. For compound I, they reveal that the principal intermolecular contacts are H⋯H (47.2%, Fig. 6 ▸ b), H⋯C/C⋯H (20.7%, Fig. 6 ▸ c), O⋯H/H⋯O (14.1%, Fig. 6 ▸ d), C⋯C (7.8%, Fig. 6 ▸ e), S⋯H/H⋯S (7.4%, Fig. 6 ▸ f), S⋯C/C⋯S (1.8%, Fig. 6 ▸ g) and N⋯H/H⋯N (0.7%, Fig. 6 ▸ h). For compound II, they reveal a similar trend, with the principal intermolecular contacts being H⋯H/H⋯H (44.6%, Fig. 7 ▸ b), H⋯C/C⋯H (29.1%, Fig. 7 ▸ c), O⋯H/H⋯O (13.6%, Fig. 7 ▸ d), C⋯C (4.6%, Fig. 7 ▸ e), S⋯H/H⋯S (4.3%, Fig. 7 ▸ f), S⋯C/C⋯S (3.3%, Fig. 7 ▸ g), C⋯O/O⋯C (0.4%, Fig. 7 ▸ h) and S⋯O/O⋯S (0.1%, Fig. 7 ▸ i). In both compounds, the H⋯H intermolecular contacts predominate, followed by C⋯H/H⋯C and O⋯H/H⋯O contacts.
Figure 6.
The full two-dimensional fingerprint plot for compound I, and fingerprint plots delineated into (b) H⋯H, (c) O⋯H/H⋯O, (d) C⋯H/H⋯C, (e) C⋯C and (f) N⋯H/H⋯N contacts.
Figure 7.
The full two-dimensional fingerprint plot for compound II, and fingerprint plots delineated into (b) C⋯C, (c) C⋯H/H⋯C, (d) C⋯·N/N⋯C, (e) C⋯O/O⋯C, (f) H⋯H, (g) N⋯H/H⋯N, (h) O⋯H/H⋯O and (I) S⋯H/H⋯S contacts.
5. Synthesis and crystallization
Compound I: A solution of N-propargylbenzenesulfonamide (0.50 g) in xylenes (20 mL), MnO2 (0.50 g) was added and the reaction mixture was refluxed for 24 h. It was then filtered through a celite pad and washed with hot xylenes (2 × 10 mL). The combined filtrate was concentrated under vacuum and then triturated with MeOH to afford dibenzo[b]thiophene (0.38 g, 92%) as a dull white solid. Finally, compound I was crystallized using ethanol.
Compound II: To a solution of (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]phenyl}benzenesulfonamide (1.2 g, 3.069 mmol) in CH3CN (10 mL), K2CO3 (0.63 g, 4.603 mmol) and propargyl bromide (0.54 mL, 4.603 mmol) were added and the mixture was stirred at room temperature for 12 h. After completion of the reaction (monitored by TLC), it was poured into crushed ice (50 g) containing conc. HCl (5 mL), extracted with ethyl acetate (2 × 20 mL) then washed with water (2 × 20 mL) and dried (Na2SO4). Removal of the solvent in vacuo followed by crystallization from methanol (4 mL) afforded compound II as a white solid.
6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. H atoms were found difference electron-density maps and positioned geometrically. They were refined as riding, with C—H = 0.93–0.94 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).
Table 3. Experimental details.
| I | II | |
|---|---|---|
| Crystal data | ||
| Chemical formula | C26H19NO2S2 | C25H19NO2S2 |
| M r | 441.54 | 429.53 |
| Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/c |
| Temperature (K) | 298 | 298 |
| a, b, c (Å) | 10.3378 (4), 19.4299 (7), 10.5128 (4) | 10.0085 (4), 8.6474 (3), 24.9024 (10) |
| β (°) | 91.666 (1) | 91.560 (2) |
| V (Å3) | 2110.73 (14) | 2154.44 (14) |
| Z | 4 | 4 |
| Radiation type | Mo Kα | Cu Kα |
| μ (mm−1) | 0.28 | 2.41 |
| Crystal size (mm) | 0.28 × 0.21 × 0.11 | 0.55 × 0.16 × 0.09 |
| Data collection | ||
| Diffractometer | Bruker D8 VENTURE with PHOTON II detector | Bruker D8 VENTURE with PHOTON II detector |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| T min, T max | 0.913, 0.952 | 0.473, 0.752 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 102594, 6426, 5503 | 51958, 4099, 3475 |
| R int | 0.049 | 0.062 |
| (sin θ/λ)max (Å−1) | 0.714 | 0.610 |
| Refinement | ||
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.039, 0.107, 1.08 | 0.053, 0.176, 1.08 |
| No. of reflections | 6426 | 4099 |
| No. of parameters | 281 | 272 |
| No. of restraints | 0 | 79 |
| H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.28, −0.41 | 0.48, −0.44 |
Supplementary Material
Crystal structure: contains datablock(s) global, I, II. DOI: 10.1107/S2056989023003821/zn2028sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989023003821/zn2028Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989023003821/zn2028IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989023003821/zn2028Isup4.cml
Supporting information file. DOI: 10.1107/S2056989023003821/zn2028IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the SAIF, IIT, Madras, India, for the data collection.
supplementary crystallographic information
5-(Phenylsulfonyl)-5,6-dihydrobenzo[4,5]thieno[3,2-j]phenanthridine (I) . Crystal data
| C26H19NO2S2 | F(000) = 920 |
| Mr = 441.54 | Dx = 1.389 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.3378 (4) Å | Cell parameters from 9927 reflections |
| b = 19.4299 (7) Å | θ = 2.7–30.5° |
| c = 10.5128 (4) Å | µ = 0.28 mm−1 |
| β = 91.666 (1)° | T = 298 K |
| V = 2110.73 (14) Å3 | Solid, white |
| Z = 4 | 0.28 × 0.21 × 0.11 mm |
5-(Phenylsulfonyl)-5,6-dihydrobenzo[4,5]thieno[3,2-j]phenanthridine (I) . Data collection
| Bruker D8 VENTURE diffractometer with PHOTON II detector | 6426 independent reflections |
| Radiation source: fine-focus sealed tube | 5503 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.049 |
| ω and φ scan | θmax = 30.5°, θmin = 3.4° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −14→14 |
| Tmin = 0.913, Tmax = 0.952 | k = −27→27 |
| 102594 measured reflections | l = −15→15 |
5-(Phenylsulfonyl)-5,6-dihydrobenzo[4,5]thieno[3,2-j]phenanthridine (I) . Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0461P)2 + 0.647P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max = 0.001 |
| 6426 reflections | Δρmax = 0.28 e Å−3 |
| 281 parameters | Δρmin = −0.41 e Å−3 |
5-(Phenylsulfonyl)-5,6-dihydrobenzo[4,5]thieno[3,2-j]phenanthridine (I) . 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. |
5-(Phenylsulfonyl)-5,6-dihydrobenzo[4,5]thieno[3,2-j]phenanthridine (I) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.18150 (12) | 0.54394 (7) | 0.49074 (12) | 0.0357 (2) | |
| C2 | 0.07837 (14) | 0.57488 (8) | 0.42365 (15) | 0.0456 (3) | |
| H2 | 0.043585 | 0.616286 | 0.450922 | 0.055* | |
| C3 | 0.02956 (15) | 0.54248 (9) | 0.31610 (16) | 0.0509 (4) | |
| H3 | −0.038513 | 0.562400 | 0.269510 | 0.061* | |
| C4 | 0.08113 (15) | 0.48034 (9) | 0.27666 (15) | 0.0486 (3) | |
| H4 | 0.046942 | 0.459128 | 0.203845 | 0.058* | |
| C5 | 0.18211 (13) | 0.44951 (7) | 0.34353 (13) | 0.0411 (3) | |
| H5 | 0.214467 | 0.407556 | 0.316150 | 0.049* | |
| C6 | 0.23642 (11) | 0.48106 (6) | 0.45270 (11) | 0.0323 (2) | |
| C7 | 0.34011 (11) | 0.45888 (6) | 0.54103 (11) | 0.0304 (2) | |
| C8 | 0.35613 (12) | 0.50602 (6) | 0.64208 (12) | 0.0326 (2) | |
| C9 | 0.44637 (12) | 0.49656 (6) | 0.74072 (12) | 0.0345 (2) | |
| H9 | 0.454519 | 0.528641 | 0.806122 | 0.041* | |
| C10 | 0.52436 (11) | 0.43836 (6) | 0.74018 (11) | 0.0314 (2) | |
| C11 | 0.62210 (12) | 0.42551 (6) | 0.84265 (11) | 0.0335 (2) | |
| C12 | 0.66959 (14) | 0.47761 (8) | 0.92326 (13) | 0.0421 (3) | |
| H12 | 0.639586 | 0.522406 | 0.912326 | 0.051* | |
| C13 | 0.76051 (15) | 0.46350 (9) | 1.01902 (14) | 0.0484 (3) | |
| H13 | 0.790176 | 0.498700 | 1.072230 | 0.058* | |
| C14 | 0.80733 (15) | 0.39763 (9) | 1.03599 (15) | 0.0504 (3) | |
| H14 | 0.868110 | 0.388423 | 1.100704 | 0.060* | |
| C15 | 0.76402 (14) | 0.34548 (8) | 0.95703 (14) | 0.0460 (3) | |
| H15 | 0.796669 | 0.301174 | 0.967394 | 0.055* | |
| C16 | 0.67120 (12) | 0.35912 (7) | 0.86155 (12) | 0.0356 (2) | |
| C17 | 0.38346 (13) | 0.27810 (7) | 0.86487 (13) | 0.0395 (3) | |
| C18 | 0.36218 (19) | 0.30659 (9) | 0.98291 (17) | 0.0586 (4) | |
| H18 | 0.427937 | 0.307864 | 1.045138 | 0.070* | |
| C19 | 0.2403 (2) | 0.33334 (11) | 1.0068 (2) | 0.0768 (6) | |
| H19 | 0.224407 | 0.352937 | 1.085500 | 0.092* | |
| C20 | 0.1442 (2) | 0.33097 (11) | 0.9155 (3) | 0.0786 (7) | |
| H20 | 0.062980 | 0.348623 | 0.932799 | 0.094* | |
| C21 | 0.16574 (18) | 0.30305 (12) | 0.7993 (2) | 0.0745 (6) | |
| H21 | 0.099453 | 0.302077 | 0.737596 | 0.089* | |
| C22 | 0.28611 (16) | 0.27605 (9) | 0.77249 (17) | 0.0548 (4) | |
| H22 | 0.300957 | 0.256810 | 0.693241 | 0.066* | |
| C23 | 0.60124 (13) | 0.32934 (7) | 0.64517 (12) | 0.0373 (3) | |
| H23A | 0.562993 | 0.291924 | 0.595934 | 0.045* | |
| H23B | 0.682220 | 0.341678 | 0.606776 | 0.045* | |
| C24 | 0.51108 (11) | 0.39059 (6) | 0.63939 (11) | 0.0308 (2) | |
| C25 | 0.42157 (11) | 0.40052 (6) | 0.53871 (11) | 0.0310 (2) | |
| C26 | 0.41359 (15) | 0.35107 (7) | 0.42818 (14) | 0.0442 (3) | |
| H26A | 0.483215 | 0.318491 | 0.435605 | 0.066* | |
| H26B | 0.420076 | 0.376139 | 0.349937 | 0.066* | |
| H26C | 0.332397 | 0.327105 | 0.428648 | 0.066* | |
| N1 | 0.62789 (10) | 0.30555 (5) | 0.77677 (11) | 0.0366 (2) | |
| O1 | 0.52000 (12) | 0.19506 (5) | 0.73109 (12) | 0.0559 (3) | |
| O2 | 0.59493 (12) | 0.22243 (6) | 0.95103 (12) | 0.0598 (3) | |
| S1 | 0.25152 (3) | 0.57621 (2) | 0.63062 (3) | 0.04119 (9) | |
| S2 | 0.53669 (3) | 0.24354 (2) | 0.83244 (3) | 0.03996 (9) |
5-(Phenylsulfonyl)-5,6-dihydrobenzo[4,5]thieno[3,2-j]phenanthridine (I) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0340 (6) | 0.0350 (6) | 0.0382 (6) | −0.0006 (5) | 0.0008 (5) | 0.0048 (5) |
| C2 | 0.0410 (7) | 0.0425 (7) | 0.0529 (8) | 0.0062 (6) | −0.0040 (6) | 0.0076 (6) |
| C3 | 0.0417 (7) | 0.0546 (9) | 0.0556 (9) | 0.0016 (6) | −0.0110 (6) | 0.0124 (7) |
| C4 | 0.0447 (7) | 0.0553 (8) | 0.0450 (7) | −0.0054 (6) | −0.0110 (6) | 0.0019 (6) |
| C5 | 0.0399 (6) | 0.0429 (7) | 0.0401 (6) | −0.0030 (5) | −0.0039 (5) | −0.0014 (5) |
| C6 | 0.0304 (5) | 0.0324 (5) | 0.0341 (5) | −0.0035 (4) | 0.0018 (4) | 0.0042 (4) |
| C7 | 0.0312 (5) | 0.0291 (5) | 0.0308 (5) | −0.0025 (4) | 0.0022 (4) | 0.0026 (4) |
| C8 | 0.0345 (5) | 0.0291 (5) | 0.0341 (6) | 0.0018 (4) | 0.0016 (4) | 0.0003 (4) |
| C9 | 0.0392 (6) | 0.0324 (5) | 0.0317 (5) | 0.0008 (5) | −0.0001 (5) | −0.0019 (4) |
| C10 | 0.0335 (5) | 0.0310 (5) | 0.0299 (5) | −0.0013 (4) | 0.0016 (4) | 0.0027 (4) |
| C11 | 0.0328 (5) | 0.0360 (6) | 0.0318 (5) | −0.0019 (4) | 0.0010 (4) | 0.0033 (4) |
| C12 | 0.0459 (7) | 0.0422 (7) | 0.0380 (6) | −0.0018 (6) | −0.0037 (5) | −0.0010 (5) |
| C13 | 0.0462 (7) | 0.0593 (9) | 0.0392 (7) | −0.0046 (6) | −0.0062 (6) | −0.0048 (6) |
| C14 | 0.0412 (7) | 0.0665 (10) | 0.0428 (7) | 0.0025 (7) | −0.0098 (6) | 0.0050 (7) |
| C15 | 0.0396 (7) | 0.0506 (8) | 0.0475 (7) | 0.0050 (6) | −0.0056 (6) | 0.0087 (6) |
| C16 | 0.0313 (5) | 0.0381 (6) | 0.0375 (6) | −0.0012 (5) | 0.0013 (4) | 0.0065 (5) |
| C17 | 0.0397 (6) | 0.0320 (6) | 0.0473 (7) | −0.0015 (5) | 0.0079 (5) | 0.0045 (5) |
| C18 | 0.0632 (10) | 0.0598 (10) | 0.0535 (9) | −0.0070 (8) | 0.0155 (8) | −0.0043 (7) |
| C19 | 0.0836 (14) | 0.0679 (12) | 0.0814 (14) | 0.0007 (10) | 0.0436 (12) | −0.0087 (10) |
| C20 | 0.0536 (10) | 0.0634 (11) | 0.1207 (19) | 0.0110 (9) | 0.0367 (12) | 0.0130 (12) |
| C21 | 0.0432 (9) | 0.0744 (13) | 0.1058 (17) | 0.0080 (9) | −0.0021 (10) | 0.0128 (12) |
| C22 | 0.0463 (8) | 0.0574 (9) | 0.0607 (9) | 0.0047 (7) | −0.0002 (7) | 0.0022 (8) |
| C23 | 0.0416 (6) | 0.0341 (6) | 0.0363 (6) | 0.0052 (5) | 0.0036 (5) | 0.0023 (5) |
| C24 | 0.0329 (5) | 0.0276 (5) | 0.0319 (5) | −0.0006 (4) | 0.0029 (4) | 0.0025 (4) |
| C25 | 0.0325 (5) | 0.0278 (5) | 0.0327 (5) | −0.0025 (4) | 0.0023 (4) | 0.0000 (4) |
| C26 | 0.0489 (7) | 0.0383 (7) | 0.0449 (7) | 0.0040 (6) | −0.0072 (6) | −0.0102 (5) |
| N1 | 0.0359 (5) | 0.0325 (5) | 0.0412 (6) | 0.0013 (4) | 0.0004 (4) | 0.0062 (4) |
| O1 | 0.0604 (7) | 0.0323 (5) | 0.0755 (8) | −0.0006 (5) | 0.0138 (6) | −0.0093 (5) |
| O2 | 0.0557 (6) | 0.0548 (6) | 0.0683 (7) | 0.0017 (5) | −0.0060 (5) | 0.0319 (6) |
| S1 | 0.04479 (18) | 0.03577 (16) | 0.04275 (18) | 0.00946 (13) | −0.00302 (13) | −0.00405 (12) |
| S2 | 0.03959 (17) | 0.02892 (14) | 0.05148 (19) | 0.00299 (11) | 0.00343 (13) | 0.00800 (12) |
5-(Phenylsulfonyl)-5,6-dihydrobenzo[4,5]thieno[3,2-j]phenanthridine (I) . Geometric parameters (Å, º)
| C1—C2 | 1.3970 (18) | C15—C16 | 1.3937 (18) |
| C1—C6 | 1.4100 (18) | C15—H15 | 0.9300 |
| C1—S1 | 1.7372 (14) | C16—N1 | 1.4334 (17) |
| C2—C3 | 1.377 (2) | C17—C22 | 1.379 (2) |
| C2—H2 | 0.9300 | C17—C18 | 1.382 (2) |
| C3—C4 | 1.388 (2) | C17—S2 | 1.7629 (14) |
| C3—H3 | 0.9300 | C18—C19 | 1.393 (3) |
| C4—C5 | 1.378 (2) | C18—H18 | 0.9300 |
| C4—H4 | 0.9300 | C19—C20 | 1.361 (3) |
| C5—C6 | 1.4038 (17) | C19—H19 | 0.9300 |
| C5—H5 | 0.9300 | C20—C21 | 1.361 (3) |
| C6—C7 | 1.4625 (16) | C20—H20 | 0.9300 |
| C7—C8 | 1.4088 (16) | C21—C22 | 1.387 (2) |
| C7—C25 | 1.4132 (16) | C21—H21 | 0.9300 |
| C8—C9 | 1.3868 (17) | C22—H22 | 0.9300 |
| C8—S1 | 1.7426 (12) | C23—N1 | 1.4770 (16) |
| C9—C10 | 1.3890 (17) | C23—C24 | 1.5117 (16) |
| C9—H9 | 0.9300 | C23—H23A | 0.9700 |
| C10—C24 | 1.4123 (16) | C23—H23B | 0.9700 |
| C10—C11 | 1.4767 (17) | C24—C25 | 1.3988 (16) |
| C11—C16 | 1.3984 (17) | C25—C26 | 1.5081 (17) |
| C11—C12 | 1.3998 (18) | C26—H26A | 0.9600 |
| C12—C13 | 1.385 (2) | C26—H26B | 0.9600 |
| C12—H12 | 0.9300 | C26—H26C | 0.9600 |
| C13—C14 | 1.378 (2) | N1—S2 | 1.6478 (11) |
| C13—H13 | 0.9300 | O1—S2 | 1.4289 (12) |
| C14—C15 | 1.376 (2) | O2—S2 | 1.4288 (11) |
| C14—H14 | 0.9300 | ||
| C2—C1—C6 | 122.51 (13) | C11—C16—N1 | 118.42 (11) |
| C2—C1—S1 | 124.41 (11) | C22—C17—C18 | 120.79 (15) |
| C6—C1—S1 | 113.05 (9) | C22—C17—S2 | 119.63 (12) |
| C3—C2—C1 | 118.29 (14) | C18—C17—S2 | 119.57 (13) |
| C3—C2—H2 | 120.9 | C17—C18—C19 | 118.66 (19) |
| C1—C2—H2 | 120.9 | C17—C18—H18 | 120.7 |
| C2—C3—C4 | 120.54 (13) | C19—C18—H18 | 120.7 |
| C2—C3—H3 | 119.7 | C20—C19—C18 | 120.39 (19) |
| C4—C3—H3 | 119.7 | C20—C19—H19 | 119.8 |
| C5—C4—C3 | 121.15 (14) | C18—C19—H19 | 119.8 |
| C5—C4—H4 | 119.4 | C21—C20—C19 | 120.74 (18) |
| C3—C4—H4 | 119.4 | C21—C20—H20 | 119.6 |
| C4—C5—C6 | 120.41 (14) | C19—C20—H20 | 119.6 |
| C4—C5—H5 | 119.8 | C20—C21—C22 | 120.3 (2) |
| C6—C5—H5 | 119.8 | C20—C21—H21 | 119.9 |
| C5—C6—C1 | 117.09 (12) | C22—C21—H21 | 119.9 |
| C5—C6—C7 | 131.20 (12) | C17—C22—C21 | 119.13 (18) |
| C1—C6—C7 | 111.65 (11) | C17—C22—H22 | 120.4 |
| C8—C7—C25 | 118.53 (10) | C21—C22—H22 | 120.4 |
| C8—C7—C6 | 110.80 (10) | N1—C23—C24 | 112.46 (10) |
| C25—C7—C6 | 130.66 (11) | N1—C23—H23A | 109.1 |
| C9—C8—C7 | 122.65 (11) | C24—C23—H23A | 109.1 |
| C9—C8—S1 | 123.92 (9) | N1—C23—H23B | 109.1 |
| C7—C8—S1 | 113.43 (9) | C24—C23—H23B | 109.1 |
| C8—C9—C10 | 118.87 (11) | H23A—C23—H23B | 107.8 |
| C8—C9—H9 | 120.6 | C25—C24—C10 | 121.66 (11) |
| C10—C9—H9 | 120.6 | C25—C24—C23 | 122.17 (11) |
| C9—C10—C24 | 119.63 (11) | C10—C24—C23 | 116.16 (10) |
| C9—C10—C11 | 121.31 (11) | C24—C25—C7 | 118.62 (10) |
| C24—C10—C11 | 119.06 (11) | C24—C25—C26 | 121.02 (11) |
| C16—C11—C12 | 117.50 (12) | C7—C25—C26 | 120.34 (11) |
| C16—C11—C10 | 119.83 (11) | C25—C26—H26A | 109.5 |
| C12—C11—C10 | 122.67 (11) | C25—C26—H26B | 109.5 |
| C13—C12—C11 | 121.04 (14) | H26A—C26—H26B | 109.5 |
| C13—C12—H12 | 119.5 | C25—C26—H26C | 109.5 |
| C11—C12—H12 | 119.5 | H26A—C26—H26C | 109.5 |
| C14—C13—C12 | 120.43 (14) | H26B—C26—H26C | 109.5 |
| C14—C13—H13 | 119.8 | C16—N1—C23 | 113.68 (10) |
| C12—C13—H13 | 119.8 | C16—N1—S2 | 118.79 (9) |
| C15—C14—C13 | 119.92 (13) | C23—N1—S2 | 117.93 (9) |
| C15—C14—H14 | 120.0 | C1—S1—C8 | 91.06 (6) |
| C13—C14—H14 | 120.0 | O2—S2—O1 | 120.00 (8) |
| C14—C15—C16 | 119.97 (14) | O2—S2—N1 | 106.79 (6) |
| C14—C15—H15 | 120.0 | O1—S2—N1 | 105.97 (7) |
| C16—C15—H15 | 120.0 | O2—S2—C17 | 107.39 (7) |
| C15—C16—C11 | 121.13 (13) | O1—S2—C17 | 107.80 (7) |
| C15—C16—N1 | 120.39 (12) | N1—S2—C17 | 108.47 (6) |
| C6—C1—C2—C3 | −0.3 (2) | C18—C19—C20—C21 | −0.6 (3) |
| S1—C1—C2—C3 | −177.95 (11) | C19—C20—C21—C22 | 0.5 (3) |
| C1—C2—C3—C4 | 0.6 (2) | C18—C17—C22—C21 | 0.0 (3) |
| C2—C3—C4—C5 | −0.1 (2) | S2—C17—C22—C21 | 179.65 (14) |
| C3—C4—C5—C6 | −0.9 (2) | C20—C21—C22—C17 | −0.2 (3) |
| C4—C5—C6—C1 | 1.19 (19) | C9—C10—C24—C25 | 0.50 (17) |
| C4—C5—C6—C7 | 178.32 (13) | C11—C10—C24—C25 | −179.03 (11) |
| C2—C1—C6—C5 | −0.62 (19) | C9—C10—C24—C23 | 179.03 (11) |
| S1—C1—C6—C5 | 177.28 (10) | C11—C10—C24—C23 | −0.50 (16) |
| C2—C1—C6—C7 | −178.29 (12) | N1—C23—C24—C25 | −146.17 (11) |
| S1—C1—C6—C7 | −0.39 (13) | N1—C23—C24—C10 | 35.31 (15) |
| C5—C6—C7—C8 | −176.35 (13) | C10—C24—C25—C7 | −2.03 (17) |
| C1—C6—C7—C8 | 0.90 (14) | C23—C24—C25—C7 | 179.53 (11) |
| C5—C6—C7—C25 | 3.9 (2) | C10—C24—C25—C26 | 176.61 (12) |
| C1—C6—C7—C25 | −178.82 (12) | C23—C24—C25—C26 | −1.83 (18) |
| C25—C7—C8—C9 | −1.59 (18) | C8—C7—C25—C24 | 2.51 (16) |
| C6—C7—C8—C9 | 178.66 (11) | C6—C7—C25—C24 | −177.79 (11) |
| C25—C7—C8—S1 | 178.72 (9) | C8—C7—C25—C26 | −176.14 (11) |
| C6—C7—C8—S1 | −1.03 (13) | C6—C7—C25—C26 | 3.56 (19) |
| C7—C8—C9—C10 | 0.05 (19) | C15—C16—N1—C23 | −143.71 (12) |
| S1—C8—C9—C10 | 179.71 (9) | C11—C16—N1—C23 | 33.72 (16) |
| C8—C9—C10—C24 | 0.51 (18) | C15—C16—N1—S2 | 70.73 (15) |
| C8—C9—C10—C11 | −179.97 (11) | C11—C16—N1—S2 | −111.84 (11) |
| C9—C10—C11—C16 | 160.90 (12) | C24—C23—N1—C16 | −52.19 (14) |
| C24—C10—C11—C16 | −19.59 (17) | C24—C23—N1—S2 | 93.69 (12) |
| C9—C10—C11—C12 | −19.40 (19) | C2—C1—S1—C8 | 177.69 (12) |
| C24—C10—C11—C12 | 160.12 (12) | C6—C1—S1—C8 | −0.16 (10) |
| C16—C11—C12—C13 | −0.8 (2) | C9—C8—S1—C1 | −178.99 (11) |
| C10—C11—C12—C13 | 179.48 (13) | C7—C8—S1—C1 | 0.70 (10) |
| C11—C12—C13—C14 | 0.7 (2) | C16—N1—S2—O2 | −45.38 (11) |
| C12—C13—C14—C15 | 0.3 (2) | C23—N1—S2—O2 | 170.52 (10) |
| C13—C14—C15—C16 | −1.2 (2) | C16—N1—S2—O1 | −174.40 (10) |
| C14—C15—C16—C11 | 1.1 (2) | C23—N1—S2—O1 | 41.49 (11) |
| C14—C15—C16—N1 | 178.41 (13) | C16—N1—S2—C17 | 70.08 (11) |
| C12—C11—C16—C15 | −0.07 (19) | C23—N1—S2—C17 | −74.03 (11) |
| C10—C11—C16—C15 | 179.65 (12) | C22—C17—S2—O2 | −152.99 (13) |
| C12—C11—C16—N1 | −177.47 (11) | C18—C17—S2—O2 | 26.65 (14) |
| C10—C11—C16—N1 | 2.25 (17) | C22—C17—S2—O1 | −22.39 (14) |
| C22—C17—C18—C19 | −0.1 (3) | C18—C17—S2—O1 | 157.25 (12) |
| S2—C17—C18—C19 | −179.73 (14) | C22—C17—S2—N1 | 91.93 (13) |
| C17—C18—C19—C20 | 0.4 (3) | C18—C17—S2—N1 | −88.43 (13) |
5-(Phenylsulfonyl)-5,6-dihydrobenzo[4,5]thieno[3,2-j]phenanthridine (I) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C23—H23A···O1 | 0.97 | 2.41 | 2.8935 (17) | 111 |
(E)-N-{2-[2-(Benzo[b]thiophen-2-yl)ethenyl]phenyl}-\ N-(prop-2-yn-1-yl)benzenesulfonamide (II) . Crystal data
| C25H19NO2S2 | F(000) = 896 |
| Mr = 429.53 | Dx = 1.324 Mg m−3 |
| Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
| a = 10.0085 (4) Å | Cell parameters from 9879 reflections |
| b = 8.6474 (3) Å | θ = 3.6–70.0° |
| c = 24.9024 (10) Å | µ = 2.41 mm−1 |
| β = 91.560 (2)° | T = 298 K |
| V = 2154.44 (14) Å3 | Solid, white |
| Z = 4 | 0.55 × 0.16 × 0.09 mm |
(E)-N-{2-[2-(Benzo[b]thiophen-2-yl)ethenyl]phenyl}-\ N-(prop-2-yn-1-yl)benzenesulfonamide (II) . Data collection
| Bruker D8 VENTURE diffractometer with PHOTON II detector | 4099 independent reflections |
| Radiation source: micro-focus sealed tube | 3475 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.062 |
| ω and φ scan | θmax = 70.2°, θmin = 3.6° |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −12→12 |
| Tmin = 0.473, Tmax = 0.752 | k = −10→9 |
| 51958 measured reflections | l = −30→30 |
(E)-N-{2-[2-(Benzo[b]thiophen-2-yl)ethenyl]phenyl}-\ N-(prop-2-yn-1-yl)benzenesulfonamide (II) . Refinement
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.1029P)2 + 0.5764P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.176 | (Δ/σ)max = 0.001 |
| S = 1.08 | Δρmax = 0.48 e Å−3 |
| 4099 reflections | Δρmin = −0.44 e Å−3 |
| 272 parameters | Extinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 79 restraints | Extinction coefficient: 0.0022 (5) |
(E)-N-{2-[2-(Benzo[b]thiophen-2-yl)ethenyl]phenyl}-\ N-(prop-2-yn-1-yl)benzenesulfonamide (II) . 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. |
(E)-N-{2-[2-(Benzo[b]thiophen-2-yl)ethenyl]phenyl}-\ N-(prop-2-yn-1-yl)benzenesulfonamide (II) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.1532 (3) | 0.9693 (3) | 0.56842 (11) | 0.0684 (6) | |
| C2 | 0.2089 (3) | 1.0879 (3) | 0.59929 (13) | 0.0840 (7) | |
| H2 | 0.294440 | 1.124310 | 0.592867 | 0.101* | |
| C3 | 0.1350 (4) | 1.1498 (4) | 0.63931 (13) | 0.0920 (9) | |
| H3 | 0.170944 | 1.229010 | 0.660409 | 0.110* | |
| C4 | 0.0074 (4) | 1.0964 (4) | 0.64899 (13) | 0.0936 (9) | |
| H4 | −0.040772 | 1.139698 | 0.676637 | 0.112* | |
| C5 | −0.0482 (3) | 0.9815 (4) | 0.61851 (12) | 0.0855 (8) | |
| H5 | −0.134220 | 0.947089 | 0.625262 | 0.103* | |
| C6 | 0.0238 (3) | 0.9148 (3) | 0.57697 (10) | 0.0682 (6) | |
| C7 | −0.0194 (3) | 0.7911 (3) | 0.54011 (10) | 0.0716 (6) | |
| H7 | −0.101598 | 0.741005 | 0.539835 | 0.086* | |
| C8 | 0.0883 (2) | 0.7615 (3) | 0.50449 (10) | 0.0668 (5) | |
| C9 | 0.0850 (3) | 0.6508 (3) | 0.46095 (11) | 0.0714 (6) | |
| H9 | 0.003002 | 0.606209 | 0.451630 | 0.086* | |
| C10 | 0.1907 (3) | 0.6081 (3) | 0.43325 (11) | 0.0702 (6) | |
| H10 | 0.273528 | 0.645705 | 0.444964 | 0.084* | |
| C11 | 0.1883 (3) | 0.5069 (3) | 0.38578 (10) | 0.0674 (6) | |
| C12 | 0.0736 (3) | 0.4882 (4) | 0.35331 (12) | 0.0824 (7) | |
| H12 | −0.004815 | 0.537783 | 0.362753 | 0.099* | |
| C13 | 0.0734 (4) | 0.3992 (4) | 0.30808 (13) | 0.0926 (9) | |
| H13 | −0.004121 | 0.390672 | 0.286857 | 0.111* | |
| C14 | 0.1880 (3) | 0.3213 (4) | 0.29349 (12) | 0.0899 (8) | |
| H14 | 0.187589 | 0.261028 | 0.262562 | 0.108* | |
| C15 | 0.3024 (3) | 0.3341 (3) | 0.32527 (11) | 0.0745 (6) | |
| H15 | 0.378979 | 0.280031 | 0.316357 | 0.089* | |
| C16 | 0.3032 (3) | 0.4275 (3) | 0.37049 (9) | 0.0642 (5) | |
| C17 | 0.6191 (2) | 0.4432 (3) | 0.33097 (10) | 0.0648 (6) | |
| C18 | 0.5938 (3) | 0.4956 (4) | 0.27912 (12) | 0.0847 (8) | |
| H18 | 0.545850 | 0.586357 | 0.273075 | 0.102* | |
| C19 | 0.6404 (4) | 0.4114 (4) | 0.23677 (13) | 0.0974 (9) | |
| H19 | 0.624473 | 0.446264 | 0.201853 | 0.117* | |
| C20 | 0.7100 (3) | 0.2772 (4) | 0.24517 (14) | 0.0903 (8) | |
| H20 | 0.739550 | 0.220487 | 0.216061 | 0.108* | |
| C21 | 0.7358 (3) | 0.2265 (4) | 0.29602 (14) | 0.0920 (9) | |
| H21 | 0.783481 | 0.135327 | 0.301581 | 0.110* | |
| C22 | 0.6919 (3) | 0.3095 (3) | 0.33956 (12) | 0.0793 (7) | |
| H22 | 0.711203 | 0.275587 | 0.374343 | 0.095* | |
| C23 | 0.4365 (3) | 0.3176 (3) | 0.44743 (10) | 0.0693 (6) | |
| H23A | 0.518561 | 0.337577 | 0.467869 | 0.083* | |
| H23B | 0.362892 | 0.327825 | 0.471735 | 0.083* | |
| C24 | 0.4395 (3) | 0.1591 (3) | 0.42754 (11) | 0.0708 (6) | |
| C25 | 0.4400 (3) | 0.0303 (3) | 0.41334 (13) | 0.0878 (8) | |
| H25 | 0.440438 | −0.072212 | 0.402039 | 0.105* | |
| N1 | 0.4216 (2) | 0.4356 (2) | 0.40484 (8) | 0.0625 (5) | |
| O1 | 0.6444 (2) | 0.5370 (2) | 0.42964 (8) | 0.0864 (6) | |
| O2 | 0.4958 (2) | 0.6818 (2) | 0.36649 (9) | 0.0859 (6) | |
| S1 | 0.22906 (7) | 0.87417 (8) | 0.51653 (3) | 0.0780 (3) | |
| S2 | 0.54870 (6) | 0.53848 (6) | 0.38576 (3) | 0.0679 (2) |
(E)-N-{2-[2-(Benzo[b]thiophen-2-yl)ethenyl]phenyl}-\ N-(prop-2-yn-1-yl)benzenesulfonamide (II) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0725 (14) | 0.0600 (13) | 0.0728 (14) | 0.0080 (10) | 0.0014 (11) | 0.0061 (10) |
| C2 | 0.0822 (17) | 0.0739 (16) | 0.0956 (19) | 0.0037 (13) | −0.0014 (14) | −0.0053 (14) |
| C3 | 0.104 (2) | 0.0820 (19) | 0.090 (2) | 0.0154 (16) | −0.0054 (16) | −0.0158 (15) |
| C4 | 0.113 (2) | 0.090 (2) | 0.0791 (18) | 0.0294 (18) | 0.0150 (16) | 0.0007 (15) |
| C5 | 0.0834 (18) | 0.0852 (19) | 0.0888 (19) | 0.0133 (14) | 0.0187 (15) | 0.0150 (14) |
| C6 | 0.0710 (13) | 0.0624 (13) | 0.0713 (13) | 0.0079 (10) | 0.0056 (11) | 0.0115 (9) |
| C7 | 0.0822 (15) | 0.0609 (13) | 0.0713 (14) | 0.0129 (11) | −0.0028 (10) | 0.0017 (10) |
| C8 | 0.0695 (13) | 0.0599 (13) | 0.0707 (13) | 0.0046 (10) | −0.0010 (10) | 0.0069 (10) |
| C9 | 0.0721 (14) | 0.0657 (14) | 0.0761 (15) | 0.0010 (11) | −0.0025 (11) | 0.0040 (11) |
| C10 | 0.0737 (14) | 0.0618 (13) | 0.0747 (15) | 0.0051 (11) | −0.0055 (11) | 0.0006 (11) |
| C11 | 0.0758 (14) | 0.0581 (12) | 0.0679 (14) | −0.0008 (11) | −0.0039 (11) | 0.0035 (10) |
| C12 | 0.0791 (17) | 0.0826 (18) | 0.0847 (18) | 0.0014 (14) | −0.0116 (14) | 0.0015 (14) |
| C13 | 0.094 (2) | 0.098 (2) | 0.0850 (19) | −0.0117 (17) | −0.0227 (16) | −0.0017 (16) |
| C14 | 0.108 (2) | 0.0894 (19) | 0.0717 (16) | −0.0138 (17) | −0.0103 (15) | −0.0140 (14) |
| C15 | 0.0880 (16) | 0.0663 (14) | 0.0691 (14) | −0.0072 (12) | −0.0006 (12) | −0.0074 (11) |
| C16 | 0.0757 (14) | 0.0539 (11) | 0.0626 (12) | −0.0039 (10) | −0.0037 (10) | 0.0008 (9) |
| C17 | 0.0708 (13) | 0.0551 (12) | 0.0687 (13) | −0.0066 (10) | 0.0020 (10) | 0.0013 (10) |
| C18 | 0.109 (2) | 0.0689 (15) | 0.0761 (16) | 0.0056 (15) | 0.0015 (15) | 0.0091 (13) |
| C19 | 0.123 (3) | 0.102 (2) | 0.0677 (17) | −0.003 (2) | 0.0072 (16) | −0.0004 (15) |
| C20 | 0.0948 (19) | 0.086 (2) | 0.0911 (19) | −0.0089 (16) | 0.0239 (16) | −0.0161 (16) |
| C21 | 0.094 (2) | 0.0775 (18) | 0.105 (2) | 0.0143 (15) | 0.0232 (17) | −0.0014 (15) |
| C22 | 0.0834 (17) | 0.0761 (16) | 0.0788 (16) | 0.0148 (13) | 0.0079 (13) | 0.0071 (13) |
| C23 | 0.0798 (15) | 0.0680 (14) | 0.0601 (13) | 0.0038 (11) | 0.0001 (11) | 0.0001 (10) |
| C24 | 0.0745 (14) | 0.0642 (14) | 0.0737 (15) | −0.0011 (11) | 0.0010 (11) | 0.0082 (11) |
| C25 | 0.102 (2) | 0.0614 (16) | 0.099 (2) | −0.0030 (14) | −0.0069 (17) | 0.0033 (14) |
| N1 | 0.0703 (11) | 0.0545 (10) | 0.0625 (11) | −0.0011 (8) | −0.0004 (8) | −0.0017 (8) |
| O1 | 0.0862 (12) | 0.0927 (14) | 0.0794 (12) | −0.0152 (10) | −0.0116 (9) | −0.0167 (10) |
| O2 | 0.1087 (14) | 0.0464 (9) | 0.1030 (14) | 0.0004 (9) | 0.0092 (11) | −0.0023 (9) |
| S1 | 0.0729 (4) | 0.0769 (5) | 0.0842 (5) | 0.0002 (3) | 0.0065 (3) | −0.0032 (3) |
| S2 | 0.0782 (4) | 0.0514 (3) | 0.0740 (4) | −0.0057 (2) | 0.0004 (3) | −0.0089 (2) |
(E)-N-{2-[2-(Benzo[b]thiophen-2-yl)ethenyl]phenyl}-\ N-(prop-2-yn-1-yl)benzenesulfonamide (II) . Geometric parameters (Å, º)
| C1—C2 | 1.389 (4) | C14—C15 | 1.379 (4) |
| C1—C6 | 1.400 (4) | C14—H14 | 0.9300 |
| C1—S1 | 1.725 (3) | C15—C16 | 1.386 (3) |
| C2—C3 | 1.366 (5) | C15—H15 | 0.9300 |
| C2—H2 | 0.9300 | C16—N1 | 1.444 (3) |
| C3—C4 | 1.385 (5) | C17—C22 | 1.380 (4) |
| C3—H3 | 0.9300 | C17—C18 | 1.385 (4) |
| C4—C5 | 1.361 (5) | C17—S2 | 1.758 (3) |
| C4—H4 | 0.9300 | C18—C19 | 1.374 (5) |
| C5—C6 | 1.401 (4) | C18—H18 | 0.9300 |
| C5—H5 | 0.9300 | C19—C20 | 1.366 (5) |
| C6—C7 | 1.467 (4) | C19—H19 | 0.9300 |
| C7—C8 | 1.437 (4) | C20—C21 | 1.358 (5) |
| C7—H7 | 0.9300 | C20—H20 | 0.9300 |
| C8—C9 | 1.446 (4) | C21—C22 | 1.382 (4) |
| C8—S1 | 1.733 (3) | C21—H21 | 0.9300 |
| C9—C10 | 1.331 (4) | C22—H22 | 0.9300 |
| C9—H9 | 0.9300 | C23—C24 | 1.457 (4) |
| C10—C11 | 1.471 (4) | C23—N1 | 1.477 (3) |
| C10—H10 | 0.9300 | C23—H23A | 0.9700 |
| C11—C12 | 1.396 (4) | C23—H23B | 0.9700 |
| C11—C16 | 1.401 (4) | C24—C25 | 1.169 (4) |
| C12—C13 | 1.364 (5) | C25—H25 | 0.9300 |
| C12—H12 | 0.9300 | N1—S2 | 1.634 (2) |
| C13—C14 | 1.386 (5) | O1—S2 | 1.433 (2) |
| C13—H13 | 0.9300 | O2—S2 | 1.426 (2) |
| C2—C1—C6 | 121.6 (3) | C14—C15—C16 | 120.0 (3) |
| C2—C1—S1 | 126.0 (2) | C14—C15—H15 | 120.0 |
| C6—C1—S1 | 112.4 (2) | C16—C15—H15 | 120.0 |
| C3—C2—C1 | 118.4 (3) | C15—C16—C11 | 121.3 (2) |
| C3—C2—H2 | 120.8 | C15—C16—N1 | 119.8 (2) |
| C1—C2—H2 | 120.8 | C11—C16—N1 | 118.8 (2) |
| C2—C3—C4 | 121.1 (3) | C22—C17—C18 | 120.1 (3) |
| C2—C3—H3 | 119.4 | C22—C17—S2 | 119.6 (2) |
| C4—C3—H3 | 119.4 | C18—C17—S2 | 120.2 (2) |
| C5—C4—C3 | 120.8 (3) | C19—C18—C17 | 119.0 (3) |
| C5—C4—H4 | 119.6 | C19—C18—H18 | 120.5 |
| C3—C4—H4 | 119.6 | C17—C18—H18 | 120.5 |
| C4—C5—C6 | 120.1 (3) | C20—C19—C18 | 121.0 (3) |
| C4—C5—H5 | 120.0 | C20—C19—H19 | 119.5 |
| C6—C5—H5 | 120.0 | C18—C19—H19 | 119.5 |
| C1—C6—C5 | 118.1 (3) | C21—C20—C19 | 120.0 (3) |
| C1—C6—C7 | 114.1 (2) | C21—C20—H20 | 120.0 |
| C5—C6—C7 | 127.8 (3) | C19—C20—H20 | 120.0 |
| C8—C7—C6 | 107.7 (2) | C20—C21—C22 | 120.5 (3) |
| C8—C7—H7 | 126.2 | C20—C21—H21 | 119.8 |
| C6—C7—H7 | 126.2 | C22—C21—H21 | 119.8 |
| C7—C8—C9 | 125.3 (2) | C17—C22—C21 | 119.4 (3) |
| C7—C8—S1 | 114.4 (2) | C17—C22—H22 | 120.3 |
| C9—C8—S1 | 120.28 (19) | C21—C22—H22 | 120.3 |
| C10—C9—C8 | 124.7 (3) | C24—C23—N1 | 114.1 (2) |
| C10—C9—H9 | 117.6 | C24—C23—H23A | 108.7 |
| C8—C9—H9 | 117.6 | N1—C23—H23A | 108.7 |
| C9—C10—C11 | 125.9 (3) | C24—C23—H23B | 108.7 |
| C9—C10—H10 | 117.1 | N1—C23—H23B | 108.7 |
| C11—C10—H10 | 117.1 | H23A—C23—H23B | 107.6 |
| C12—C11—C16 | 117.0 (2) | C25—C24—C23 | 177.5 (3) |
| C12—C11—C10 | 122.0 (2) | C24—C25—H25 | 180.0 |
| C16—C11—C10 | 121.0 (2) | C16—N1—C23 | 117.24 (19) |
| C13—C12—C11 | 121.7 (3) | C16—N1—S2 | 119.12 (16) |
| C13—C12—H12 | 119.1 | C23—N1—S2 | 121.40 (17) |
| C11—C12—H12 | 119.1 | C1—S1—C8 | 91.47 (13) |
| C12—C13—C14 | 120.5 (3) | O2—S2—O1 | 119.89 (13) |
| C12—C13—H13 | 119.7 | O2—S2—N1 | 106.65 (11) |
| C14—C13—H13 | 119.7 | O1—S2—N1 | 106.44 (12) |
| C15—C14—C13 | 119.4 (3) | O2—S2—C17 | 107.41 (12) |
| C15—C14—H14 | 120.3 | O1—S2—C17 | 108.30 (13) |
| C13—C14—H14 | 120.3 | N1—S2—C17 | 107.60 (11) |
| C6—C1—C2—C3 | 1.0 (4) | C22—C17—C18—C19 | 0.9 (5) |
| S1—C1—C2—C3 | −179.4 (2) | S2—C17—C18—C19 | −174.4 (3) |
| C1—C2—C3—C4 | −0.2 (5) | C17—C18—C19—C20 | 0.6 (5) |
| C2—C3—C4—C5 | −0.5 (5) | C18—C19—C20—C21 | −1.1 (5) |
| C3—C4—C5—C6 | 0.4 (5) | C19—C20—C21—C22 | 0.2 (5) |
| C2—C1—C6—C5 | −1.1 (4) | C18—C17—C22—C21 | −1.8 (4) |
| S1—C1—C6—C5 | 179.3 (2) | S2—C17—C22—C21 | 173.6 (2) |
| C2—C1—C6—C7 | 179.0 (2) | C20—C21—C22—C17 | 1.2 (5) |
| S1—C1—C6—C7 | −0.6 (3) | C15—C16—N1—C23 | −86.4 (3) |
| C4—C5—C6—C1 | 0.4 (4) | C11—C16—N1—C23 | 89.3 (3) |
| C4—C5—C6—C7 | −179.8 (3) | C15—C16—N1—S2 | 76.8 (3) |
| C1—C6—C7—C8 | −0.1 (3) | C11—C16—N1—S2 | −107.4 (2) |
| C5—C6—C7—C8 | −180.0 (2) | C24—C23—N1—C16 | 59.7 (3) |
| C6—C7—C8—C9 | −178.1 (2) | C24—C23—N1—S2 | −103.1 (2) |
| C6—C7—C8—S1 | 0.8 (3) | C2—C1—S1—C8 | −178.7 (3) |
| C7—C8—C9—C10 | −169.8 (3) | C6—C1—S1—C8 | 0.87 (19) |
| S1—C8—C9—C10 | 11.4 (4) | C7—C8—S1—C1 | −1.0 (2) |
| C8—C9—C10—C11 | −174.1 (2) | C9—C8—S1—C1 | 178.0 (2) |
| C9—C10—C11—C12 | 23.3 (4) | C16—N1—S2—O2 | 45.4 (2) |
| C9—C10—C11—C16 | −158.3 (3) | C23—N1—S2—O2 | −152.10 (18) |
| C16—C11—C12—C13 | −1.2 (4) | C16—N1—S2—O1 | 174.46 (17) |
| C10—C11—C12—C13 | 177.2 (3) | C23—N1—S2—O1 | −23.0 (2) |
| C11—C12—C13—C14 | 1.3 (5) | C16—N1—S2—C17 | −69.6 (2) |
| C12—C13—C14—C15 | 0.2 (5) | C23—N1—S2—C17 | 92.91 (19) |
| C13—C14—C15—C16 | −1.8 (5) | C22—C17—S2—O2 | 172.2 (2) |
| C14—C15—C16—C11 | 1.9 (4) | C18—C17—S2—O2 | −12.4 (3) |
| C14—C15—C16—N1 | 177.5 (2) | C22—C17—S2—O1 | 41.4 (2) |
| C12—C11—C16—C15 | −0.4 (4) | C18—C17—S2—O1 | −143.2 (2) |
| C10—C11—C16—C15 | −178.8 (2) | C22—C17—S2—N1 | −73.3 (2) |
| C12—C11—C16—N1 | −176.0 (2) | C18—C17—S2—N1 | 102.1 (2) |
| C10—C11—C16—N1 | 5.5 (3) |
(E)-N-{2-[2-(Benzo[b]thiophen-2-yl)ethenyl]phenyl}-\ N-(prop-2-yn-1-yl)benzenesulfonamide (II) . Hydrogen-bond geometry (Å, º)
Cg1 is the centroid of the C1–C6 ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C23—H23A···O1 | 0.97 | 2.35 | 2.860 (3) | 112 |
| C25—H25···O2i | 0.93 | 2.38 | 3.285 (4) | 166 |
| C21—H21···Cg1ii | 0.93 | 2.97 | 3.772 (2) | 139 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1.
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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) global, I, II. DOI: 10.1107/S2056989023003821/zn2028sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989023003821/zn2028Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989023003821/zn2028IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989023003821/zn2028Isup4.cml
Supporting information file. DOI: 10.1107/S2056989023003821/zn2028IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report