Abstract
C17H9ClN2O2, triclinic,
The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Colourless block |
| Size: | 0.21 × 0.15 × 0.11 mm |
| Wavelength: | Cu Kα radiation (1.54184 Å) |
| μ: | 2.52 mm−1 |
| Diffractometer, scan mode: | SuperNova, ω |
| θmax, completeness: | 73.6°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 4378, 2684, 0.012 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 2519 |
| N(param)refined: | 199 |
| Programs: | CrysAlisPRO [1], Olex2 [2], SHELX [3, 4] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| Cl1 | −0.09394 (8) | 0.82222 (8) | 0.74406 (4) | 0.0689 (2) |
| O1 | 0.09789 (19) | 0.6497 (2) | 0.21944 (12) | 0.0584 (4) |
| O2 | 0.51686 (19) | 0.6988 (2) | 0.39965 (13) | 0.0654 (4) |
| N1 | 0.34452 (19) | 0.6585 (2) | 0.28782 (12) | 0.0443 (3) |
| N2 | 0.5263 (2) | 0.2934 (2) | 0.24958 (13) | 0.0492 (4) |
| C1 | 0.0678 (2) | 0.7107 (2) | 0.40240 (14) | 0.0413 (3) |
| C2 | 0.1957 (2) | 0.7235 (2) | 0.45732 (14) | 0.0415 (4) |
| C3 | 0.5698 (2) | 0.4297 (2) | 0.17598 (14) | 0.0417 (4) |
| C4 | 0.1609 (2) | 0.6690 (2) | 0.29257 (14) | 0.0433 (4) |
| C5 | 0.3747 (2) | 0.6934 (2) | 0.38365 (15) | 0.0448 (4) |
| C6 | 0.4822 (2) | 0.6172 (2) | 0.19531 (14) | 0.0439 (4) |
| C7 | 0.7000 (2) | 0.3942 (3) | 0.08110 (15) | 0.0468 (4) |
| C8 | 0.1516 (2) | 0.7578 (3) | 0.56276 (15) | 0.0478 (4) |
| H8 | 0.237623 | 0.766199 | 0.599639 | 0.057* |
| C9 | −0.0294 (3) | 0.7790 (2) | 0.61070 (15) | 0.0483 (4) |
| C10 | −0.1596 (3) | 0.7666 (3) | 0.55747 (16) | 0.0510 (4) |
| H10 | −0.278957 | 0.781186 | 0.592914 | 0.061* |
| C11 | −0.1116 (2) | 0.7324 (3) | 0.45076 (16) | 0.0489 (4) |
| H11 | −0.197367 | 0.724525 | 0.413400 | 0.059* |
| C12 | 0.5290 (3) | 0.7556 (3) | 0.12776 (17) | 0.0556 (4) |
| H12 | 0.473255 | 0.876498 | 0.142816 | 0.067* |
| C13 | 0.7431 (3) | 0.5407 (3) | 0.01106 (16) | 0.0557 (5) |
| H13 | 0.827275 | 0.517372 | −0.051652 | 0.067* |
| C14 | 0.7854 (3) | 0.2064 (3) | 0.06340 (18) | 0.0581 (5) |
| H14 | 0.869949 | 0.176299 | 0.001588 | 0.070* |
| C15 | 0.6128 (3) | 0.1211 (3) | 0.22912 (19) | 0.0581 (5) |
| H15 | 0.585777 | 0.026217 | 0.278956 | 0.070* |
| C16 | 0.6618 (3) | 0.7165 (3) | 0.03485 (18) | 0.0619 (5) |
| H16 | 0.694102 | 0.811649 | −0.010451 | 0.074* |
| C17 | 0.7428 (3) | 0.0711 (3) | 0.1373 (2) | 0.0630 (5) |
| H17 | 0.798944 | −0.053042 | 0.127378 | 0.076* |
Source of material
All of reagents were purchased with analysis grade. 2.82 g 3-chloro-N-(quinolin-8-yl)benzamide (10 mmol), 0.38 g anhydrous copper nitrate (2 mmol), 4.15 g 2,2′-azobisisobutyronitrile (25 mmol), and 1.34 g silver acetate (8 mmol) were added to 40 mL distilled acetonitrile in a borosil sealed tube. The tube was heated at 403 K under oxygen atmosphere for 8 h, then cooled to room temperature and filtered. The filtrate evaporated slowly in air. A few days later, colourless crystals were harvested, yield 38% (based on 3-chloro-N-(quinolin-8-yl)benzamide).
Experimental details
Single crystal X-ray diffraction data were collected at 293 K using an Agilent Super Nova diffractometer equipped with a Dual source (Cu at Home/Near) and an Atlas S2 detector. The structure was solved by direct methods with the SHELXS-2018 program. All H-atoms attached to C atoms were positioned with idealized geometry and refined isotropically (Uiso(H) = 1.2Ueq(C)) using a riding model with C–H = 0.930 Å. Structural refinement suggests the possible presence of a small amount (< 5%) of disorder of the Cl atom between the 5- and 6- positions on the isoindoline ring.
Comment
The aerobic carbonylation of C(sp2)–H with less toxic 2,2′-azobisisobutyronitrile using transition metal salts as the effective catalysts has attracted a lot of interest. Through this way many N-quinolyl substituted phthalimide derivatives have been studied and some of their crystal structures have also been reported [5], [6], [7], [8]. However, the crystal of the title compound, 5-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione (CQDD), has not been reported. CQDD crystalizes in the triclinic space group
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: None declared.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
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© 2021 Wei Zhang et al., published by De Gruyter, Berlin/Boston
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