Abstract
C17H13Cl1N2, monoclinic, P21/c (no. 14), a = 7.830(2) Å, b = 26.688(8) Å, c = 7.362(2) Å, β = 115.366(3)°, V = 1390.1(7) Å3, Z = 4, Rgt(F) = 0.0604, wRref(F2) = 0.1761, T = 296(2) K.
The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Block |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 0.27 cm−1 |
| Diffractometer, scan mode: | Bruker APEX-II, φ and ω-scans |
| θmax, Completeness: | 25°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 13162, 2450, 0.019 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 2043 |
| N(param)refined: | 181 |
| Programs: | Bruker programs [1], SHELX [2] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| Cl1 | 0.84345(14) | 0.05408(4) | 0.04791(16) | 0.1146(5) |
| C1 | 0.5087(4) | −0.16423(8) | 0.7024(4) | 0.0477(6) |
| N1 | 0.7461(3) | −0.11992(8) | 0.6442(3) | 0.0575(6) |
| H1 | 0.8485 | −0.1026 | 0.6950 | 0.069* |
| N2 | 0.4288(3) | −0.10693(9) | 0.4274(3) | 0.0594(6) |
| H2 | 0.3580 | −0.0826 | 0.3600 | 0.071* |
| C2 | 0.7028(4) | −0.15438(9) | 0.7587(4) | 0.0487(6) |
| C6 | 0.4554(4) | −0.19745(9) | 0.8204(4) | 0.0570(7) |
| C10 | 0.3679(4) | −0.14081(9) | 0.5303(4) | 0.0510(6) |
| C15 | 0.7723(4) | 0.00574(11) | 0.1588(4) | 0.0640(8) |
| C12 | 0.6697(4) | −0.07037(11) | 0.3424(4) | 0.0603(7) |
| C5 | 0.5993(5) | −0.21972(10) | 0.9916(5) | 0.0684(8) |
| H5 | 0.5672 | −0.2411 | 1.0719 | 0.082* |
| C9 | 0.1803(4) | −0.15090(11) | 0.4774(5) | 0.0655(7) |
| H9 | 0.0873 | −0.1356 | 0.3652 | 0.079* |
| C3 | 0.8395(4) | −0.17769(10) | 0.9256(4) | 0.0613(7) |
| H3 | 0.9669 | −0.1718 | 0.9615 | 0.074* |
| C11 | 0.6143(4) | −0.11414(11) | 0.4380(4) | 0.0640(7) |
| H11 | 0.6145 | −0.1448 | 0.3650 | 0.077* |
| C17 | 0.6839(4) | −0.07822(11) | 0.1668(5) | 0.0680(8) |
| H17 | 0.6576 | −0.1098 | 0.1081 | 0.082* |
| C13 | 0.7044(5) | −0.02322(13) | 0.4253(5) | 0.0792(9) |
| H13 | 0.6926 | −0.0173 | 0.5438 | 0.095* |
| C7 | 0.2607(5) | −0.20678(11) | 0.7595(5) | 0.0714(8) |
| H7 | 0.2225 | −0.2284 | 0.8342 | 0.086* |
| C14 | 0.7570(5) | 0.01559(12) | 0.3348(5) | 0.0803(9) |
| H14 | 0.7812 | 0.0474 | 0.3915 | 0.096* |
| C4 | 0.7847(5) | −0.21022(11) | 1.0401(4) | 0.0694(8) |
| H4 | 0.8772 | −0.2257 | 1.1521 | 0.083* |
| C16 | 0.7359(4) | −0.04066(13) | 0.0749(5) | 0.0724(8) |
| H16 | 0.7463 | −0.0468 | −0.0443 | 0.087* |
| C8 | 0.1292(5) | −0.18432(12) | 0.5926(6) | 0.0740(9) |
| H8 | 0.0019 | −0.1913 | 0.5537 | 0.089* |
Source of material
A mixture of naphthalene-1,8-diamine (1.58 g, 10 mmol) and 4-chlorobenzaldehyde (1.40 g, 10 mmol), in anhydrous ethanol (50 mL) was refluxed at 353 K for about 1.5 h. Then the solvent was removed under reduced presure. The resulting residue was purified by recrystallization from ethanol (yield 2.52 g, 90%).
Experimental details
All hydrogen atoms were identified in difference Fourier syntheses. In the final stages they were positioned geometrically. The Uiso values of the hydrogen atoms were set to 1.2Ueq(C).
Discussion
Multi-nuclear N-heterocyclic compounds like perimidines have drawn extensive examinations of many researchers for a long time, because they exhibit a diverse range of biological activities [3], [4], [5]. There are several preparative methods for the synthesis of perimidine derivatives [6], [7], [8].
In the structure, the bond angles of N(1)–C(11)–N(2), N(1)–C(11)–C(12) and N(2)–C(11)–C(12) are 109.0(2), 110.8(2) and 110.8(2) in turn, which indicates the sp3 hybridization state of C(11) atom and the new-formed three-membered heterocyclic ring is nor planar. Bond lengths and angles are in the expected ranges [9].
Acknowledgements
This work was financially supported by the Natural Science Foundation of Hunan Province of China (2017JJ3093).
References
Bruker: APEX2, SAINT and SADABS. Brucker AXS Inc., Madison, WI, USA (2009).Search in Google Scholar
Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar
Bu, X.; Deady, L. W.; Finlay, G. J.; Baguley, B. C.; Denny, W. A.: Synthesis and cytotoxic activity of 7-Oxo-7H-dibenz[f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidine derivatives. J. Med. Chem. 44 (2001) 2004–2014.10.1021/jm010041lSearch in Google Scholar
Ye, J.; Sun, X. X.; Qiu, S. Y.; Hu, A. X.: Synthesis, crystal structure and fungicidal activity of N-(4-tert-buty)-5-(1,2,4-triazol-1-yl)thiazol-2-yl) propionamide. Chin. J. Struct. Chem. 3 (2014) C429–C433.Search in Google Scholar
Fu, C. R.; Pei, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.; Yang, H. Z.; Zou, X. M.: Synthesis and insecticidal activities of novel pyrazole oxime ether derivatives with different substituted pyridyl rings. Pest Manag. Sci. 70 (2013) C1207–C1214.10.1002/ps.3672Search in Google Scholar
Hendrickson, J. B.; Hussoin, M. S.: Seeking the ideal dehydrating reagent. J. Org. Chem. 52 (1987) 4137–4139.10.1021/jo00227a041Search in Google Scholar
Vanden, E. J.; Delfosse, F.; Mayence, A.; Haverbeke, Y. V.: Old reagents, new results-aromatization of Hantzsch 1,4-dihydropyridines with manganese-dioxide and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Tetrahedron 51 (1995) 5813–5818.10.1016/0040-4020(95)00318-3Search in Google Scholar
Deady, L. W.; Rodemann, T. J.: Synthesis of perimidine and fused perimidine derivatives from reaction of 1,8-naphthalenediamine with an iminoisocoumarin. Heterocycl. Chem. 35 (1998) 1417–1419.10.1002/jhet.5570350633Search in Google Scholar
Grimmer, C. D.: Crystal structure of phenyl(2-phenyl-2,3-dihydro-1H-perimidin2yl)methanone, C24H18N2O. Z. Kristallogr. NCS 232 (2017) 289–290.10.1515/ncrs-2016-0242Search in Google Scholar
©2018 Zhong-Yan Li et al., published by De Gruyter, Berlin/Boston
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.
