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The Crystal Structure of Phthalazin-1 (2H)-One, C8H6N2O1

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The Crystal Structure of Phthalazin-1 (2H)-One, C8H6N2O1 Z. Kristallogr. NCS 2018; 233(4): 605–606 Zhang Yun-Chena, Guo Hong-Meia, Li Peng-Fei, Liu Qing-Yun and Tai Xi-Shi* The crystal structure of phthalazin-1(2H)-one, C8H6N2O1 Table 1: Data collection and handling. Crystal: Yellow block Size: 0.18 × 0.17 × 0.16 mm Wavelength: Mo Kα radiation (0.71073 Å) µ: 0.10 mm−1 Diffractometer, scan mode: Bruker CCD, ω-scans θmax, completeness: 27.5°, >99% N(hkl)measured, N(hkl)unique, Rint: 13032, 3138, 0.037 Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2245 N(param)refined: 199 Programs: CrysAlisPRO [1], SHELX [2], DIAMOND [3] https://doi.org/10.1515/ncrs-2017-0363 Received January 8, 2018; accepted April 4, 2018; available online April 18, 2018 hexahydrate (0.5 mmol, 0.216 g) were dissolved in 20 mL H2O/CH3CH2OH (v:v = 1:3). The mixture was stirred for 5 h at Abstract 70 °C. Then the solution is quietly placed. The yellow crystal of C8H6N2O1, monoclinic, P21/c (no. 14), a = 8.6277(17) Å, b = phthalazin-1(2H)-one was obtained after 3 weeks. Yield: 71%. 3 13.134(3) Å, c = 13.062(5) Å, β = 110.54(3)°, V = 1386.0(7) Å , MS (FAB): 147 (M + 1). 2 Z = 8, Rgt(F) = 0.0512, wRref(F ) = 0.1581, T = 293(2) K. Experimental details CCDC no.: 1834694 Coordinates of hydrogen atoms were refined without any The asymmetric unit, containing two independent molecules, constraints or restraints. Their Uiso values were set to 1.2Ueq of the title crystal structure is shown in the figure. Tables 1 and of the parent atoms. 2 contain details on crystal structure and measurement con- ditions and a list of the atoms including atomic coordinates Comment and displacement parameters. Nitrogen heterocyclic compounds have received more atten- tion [4, 5]. Phthalazin-1(2H)-one derivatives as an important Source of materials nitrogen heterocyclic compound show good biological activ- 2-Carboxybenzaldehyde (1.0 mmol, 0.150 g), 4-phenylsemi- ities. For example, it was found that 4-(4-chlorobenzyl)-2- carbazide (1.0 mmol, 0.151 g) and lanthanum(III) nitrate methylphthalazin-1(2H)-one shows a good inhibitory effect on dermatophytes, cryptococcus, and some clinical isolates aZhang Yun-Chen and Guo Hong-Mei: These authors contributed [6]. Wang et al. reported that 4-(thiophen-2-ylmethyl)-2H- equally to this study. phthalazin-1-ones could be used as potent PARP-1 inhibitors *Corresponding author: Tai Xi-Shi, College of Chemistry and [7]. Sridhara has also reported some new phthalazin-1(2H)- Chemical Engineering, Weifang University, Weifang, Shandong one derivatives and studied their antimicrobial activities and 261061, P.R. China, e-mail: [email protected] cytotoxicity [8]. We have reported some nitrogen heterocyclic Zhang Yun-Chen: College of Chemistry and Chemical Engineering, Weifang University, Weifang, Shandong 261061, P.R. China compound and studied their antibacterial activity and anti- Guo Hong-Mei: Department of Veterinary Medicine, Shandong tumor activity [9–12]. In this paper, a new one-pot synthetic Vocational Animal Science and Veterinary College, Weifang, method was adopted to synthesized phthalazin-1(2H)-one Shandong 261061, P.R. China with 2-carboxybenzaldehyde and lanthanum(III) nitrate as Li Peng-Fei: College of Chemical Engineering, Qingdao University catalyst. of Science and Technology, Qingdao, Shandong 266061, P.R. China Liu Qing-Yun: College of Chemistry and Environmental Engineering, In the title compound, the bond lengths of C7–O1 and Shandong University of Science and Technology, Qingdao, C14–O2 are 1.2338(16) Å and 1.2418(16) Å, which indicates Shandong 266590, P.R. China that they are keto configuration. The other bond lengths Open Access. © 2018 Zhang Yun-Chen et al., published by De Gruyter. This work is licensed under the Creative Commons Attribution- NonCommercial-NoDerivatives 4.0 License. 606 | Yun-Chen et al.: C8H6N2O1 Table 2: Fractional atomic coordinates and isotropic or equivalent (ZR2014BL003), the project of Shandong Province Higher 2 isotropic displacement parameters (Å ). Educational Science and Technology Program (J14LC01) and Science Foundation of Weifang. Atom x y z Uiso*/Ueq O1 −0.84243(13) 0.04037(8) −0.04692(8) 0.0620(3) References O2 −0.17390(13) −0.27718(9) 0.34484(8) 0.0677(4) N1 −0.66639(14) 0.03685(9) 0.12816(9) 0.0517(3) 1. Oxford Diffraction: CrysAlisPRO. Oxford Diffraction, Yarnton, H1 −0.7129 0.0915 0.1395 0.062* England (2000). N2 −0.53958(16) −0.00063(10) 0.21561(10) 0.0576(3) 2. Sheldrick, G. M.: Crystal structure refinement with SHELXTL. N3 −0.01109(15) −0.27420(10) 0.52333(10) 0.0559(3) Acta Crystallogr. C71 (2015) 3–8. H3A −0.0634 −0.3272 0.5324 0.067* 3. Brandenburg, K.: DIAMOND. Visual Crystal Structure Infor- N4 0.11120(18) −0.23882(10) 0.61446(10) 0.0637(4) mation System. Ver. 3.2. Crystal Impact, Bonn, Germany C1 −0.69882(18) −0.14301(10) −0.09423(11) 0.0498(3) (2012). H1A −0.7878 −0.1172 −0.1518 0.060* 4. Liu, Q.-Y.; Zhu, J.-Q.; Sun, T.; Zhou, H.-Y.; Shao, Q.; Li, G.-J.; C2 −0.6176(2) −0.22821(11) −0.10878(13) 0.0600(4) Liu, X.-D.; Yin, Y.-S.: Porphyrin nanotubes composed of highly H2 −0.6521 −0.2610 −0.1762 0.072* ordered molecular arrays prepared by anodic aluminum 3 C3 −0.4829(2) −0.26585(12) −0.02245(14) 0.0660(5) template method. RSC Adv. (2013) 2765–2769. H3 −0.4263 −0.3225 −0.0338 0.079* 5. Vila, N.; Besada, P.; Costas, T.; Costas-Lago, M. C.; Terán, C4 −0.4320(2) −0.22085(11) 0.07906(13) 0.0595(4) C.: Phthalazin-1(2H)-one as a remarkable scaffold in drug discovery. Eur. J. Med. Chem. 97 (2015) 462–482. H4 −0.3433 −0.2476 0.1362 0.071* 6. Derita, M.; Olmo, E.-D.; Barboza, B.; Garcia-Cadenas, A.- C5 −0.51541(16) −0.13426(10) 0.09538(11) 0.0457(3) E.; López-Pérez, J. L.; Andújar, S.; Enriz, D.; Zacchino, S.; C6 −0.46988(18) −0.08258(11) 0.19859(11) 0.0542(4) Feliciano, A.-S.: Synthesis, bioevaluation and structural study H6 −0.3843 −0.1101 0.2572 0.065* of substituted phthalazin-1(2H)-ones acting as antifungal C7 −0.72784(16) −0.00225(10) 0.02505(11) 0.0452(3) agents. Molecules 18 (2013) 3479–3501. C8 −0.64710(16) −0.09490(9) 0.00785(10) 0.0418(3) 7. Wang, L.-X.; Zhou, X.-B.; Xiao, M.-L.; Jiang, N.; Liu, F.; C9 0.2485(2) −0.02416(13) 0.48736(14) 0.0676(5) Zhou, W.-X.; Wang, X.-K.; Zheng, Z.-B.; Li, S.: Synthesis and H9 0.3325 0.0019 0.5478 0.081* biological evaluation of substituted 4-(thiophen-2-ylethyl)-2H- C10 0.2151(2) 0.01896(13) 0.38601(14) 0.0725(5) phthalazin-1-ones as potent PARP-1 inhibitors. Bioorg. Med. H10 0.2777 0.0741 0.3782 0.087* Chem. Lett. 24 (2014) 3739–3743. − C11 0.0889(2) 0.01885(12) 0.29494(13) 0.0617(4) 8. Sridhara, A.-M.: Synthesis, antimicrobial and cytotoxicity H11 0.0667 0.0120 0.2272 0.074* studies of some novel modified strobilurin derivatives. J. Brazil. − − C12 0.00259(17) 0.10091(11) 0.30436(11) 0.0511(4) Chem. Soc. 22 (2011) 849–856. H12 −0.0857 −0.1266 0.2431 0.061* 9. Tai, X.-S.; Meng, Q.-G.; Liu, L.-L.: Synthesis, crystal structure, C13 0.02968(15) −0.14593(10) 0.40676(10) 0.0436(3) and cytotoxic activity of a novel eight-coordinated dinuclear C14 −0.06045(17) −0.23598(11) 0.42009(11) 0.0483(3) Ca(II)-Schiff base complex. Crystals 6 (2016) 109. C15 0.1887(2) −0.15904(12) 0.60113(12) 0.0619(4) 10. Tai, X.-S.; Wang, X.: Synthesis, characterization and antitumor H15 0.2723 −0.1331 0.6619 0.074* activity of a Ca (II) cordination polymer based on 3-amino-2- C16 0.15498(18) −0.10753(10) 0.49880(11) 0.0499(3) pyrazinecarboxylic acid. Sci. Study Res. Chem. Chem. Eng. Biotechnol. Food Ind. 16 (2015) 253–259. 11. Tai, X.-S.; Zhao, W.-H.; Li, F.-H.: Synthesis, structural character- are in agreement with those reported in refs. [13, 14]. The ization and antitumor activity of a Ca(II)-schiff base complex. intermolecular NH··· O hydrogen bonds play an impor- Chin. J. Inorg. Chem. 29 (2013) 1328–1332. tant role in the formation of phthalazin-1(2H)-one crystals. 12. Tai, X.-S.; Wang, X.; You, H.-Y.: Synthesis, crystal structure and antitumor activity of a new Zn(II) complex based on N-acetyl-L- The title compound molecules form 1D chained structure phenylalanine and 1,10-phenanthroline. Chin. J. Struct. Chem. though intermolecular hydrogen bonds. Meanwhile, the title 35 (2016) 586–590. molecules are assembled into 3D network structure though 13. Wang, L.-H.; Tai, X.-S.: The synthesis and crystal structure of weak non-classical interaction. The reported structure is a two new hydrazone compounds. Crystals 6 (2016) 57. second polymorph of the title compound [15]. 14. Tai, X.-S.; Yin, J.; Kong, F.-Y.: Crystal structure of 2- carboxybenzaldehyde furan-2-carbohydrazide methanol hemisolvate. Z. Kristallogr. NCS 222 (2007) 401–402. Acknowledgements: This project was supported by 15. Buyukgungor, O.; Odabasoglu, M.; Narayana, B.; Vijesh, A. M.; the National Natural Science Foundation of China Yathirajan, H. S.: Phthalazin-1(2H)-one. Acta Crystallogr.
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