4-Chloro-5-(morpholin-4-yl)-2-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]pyridazin-3(2H)-one

data reports 4-Chloro-5-(morpholin-4-yl)-2-[(5-phenyl-1,3,4oxadiazol-2-yl)methyl]pyridazin-3(2H)-one ISSN 2414-3146 Yanwen Sun, Haolei Wu, Changheng Wei, Mei Gao, Zeyi Shen and Hongsen Li* College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, People’s Republic of China. *Correspondence e-mail: Received 28 February 2017 Accepted 8 March 2017 Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland Keywords: crystal structure; 1,3,4-oxadiazole; pyridazin-3-one; morpholino; hydrogen bonding. In the title compound, C17H16ClN5O3, the phenyl and the oxadiazole rings are almost coplanar, subtending a dihedral angle of 4.34 (19) . These rings lie almost normal to the pyridazine ring, making dihedral angles of 87.35 (16) and 89.06 (15) , respectively. The morpholine ring has the usual chair conformation and its mean plane is inclined to the pyridazine ring by 39.45 (17) . There is a short intramolecular C—H  Cl contact present. In the crystal, molecules are linked by bifurcated C—(H,H)  O hydrogen bonds and a C—H  N hydrogen bond, forming layers parallel to the ab plane. CCDC reference: 1536569 Structural data: full structural data are available from iucrdata.iucr.org Structure description 1,3,4-Oxadiazole derivatives are a promising field of study because they possess good bioactivity (Liu et al., 2014). This substructural unit has been used as a scaffold to design and synthesize chemical compounds with biological, medicinal and agricultural activities (Gan et al., 2016; Shaikh & Meshram, 2016; Luqman et al., 2015; Fershtat et al. 2016; Pattison et al., 2009). A series of oxadiazoles containing a pyridazinone ring have been designed and synthesized, and we report herein on the crystal structure of one such compound. The molecular structure of the title compound is shown in Fig. 1. The phenyl (C1–C6) and the oxadiazole (O1/N1/N2/C7/C8) rings are almost coplanar, subtending a dihedral angle of 4.34 (19) . These rings lie almost normal to the pyridazine (N3/N4/C10–C13) ring, making dihedral angles of 87.35 (16) and 89.06 (15) , respectively. The morpholine (O3/N5/C14–C17) ring has a chair conformation and its mean plane is inclined to the pyridazine ring by 39.45 (17) . There is a short intramolecular C—H  Cl contact present (Table 1, Fig. 1). IUCrData (2017). 2, x170370 https://doi.org/10.1107/S2414314617003704 1 of 3 data reports Table 1 Hydrogen-bond geometry (Å,  ). D—H  A D—H H  A D  A D—H  A C17—H17A  Cl1 C14—H14B  O2i C13—H13  O2ii C9—H9A  N2iii 0.97 0.97 0.93 0.97 2.57 2.57 2.60 2.50 3.252 (3) 3.373 (4) 3.507 (3) 3.310 (4) 127 141 165 141 Figure 1 Symmetry codes: (i) x þ 1; y þ 12; z þ 32; (ii) x; y þ 12; z þ 32; (iii) x  1; y; z. The molecular structure of the title compound, with the atom labelling and displacement ellipsoids drawn at the 50% probability level. Table 2 Experimental details. In the crystal, molecules are linked by bifurcated C— (H,H)  O hydrogen bonds and C—H  N hydrogen bond bonds, forming layers parallel to the ab plane (Table 1 and Fig. 2). Crystal data Chemical formula Mr Crystal system, space group Temperature (K) a, b, c (Å) V (Å3) Z Radiation type  (mm1) Crystal size (mm) C17H16ClN5O3 373.80 Orthorhombic, P212121 293 4.7931 (7), 10.4177 (15), 33.685 (5) 1682.0 (4) 4 Mo K 0.26 0.20  0.16  0.11 Synthesis and crystallization To a three-necked flask, 4,5-dichloro-2-((5- phenyl-1,3,4-oxadiazol-2-yl)methyl)-pyridazin-3-(2H)-one (3.0 g, 9.3 mmol; Li et al., 2005) and morpholine (14.0 mmol, 1.22 g) were added and reacted at 333 K for 8 h in the presence of potassium carbonate (2 g) and 20 ml dry DMF. The reaction was monitored by TLC. On completion of the reaction, the mixture was poured into ice–water. The precipitate formed was collected by filtration, dried to give the pure title compound (yield 2.23 g, 64.2%). It was recrystallized from chloroform, ethyl acetate and petroleum (2:2:5) to give pale-yellow prismatic crystals (m.p. 461–463 K). 1 H NMR (CDCl3): 3.47 (t, 4H), 3.86 (t, 4H), 5.64 (s, 2H), 7.53 (m, 3H), 7.68 (s, 1H), 8.06 (m, 2H). IR (KBr, cm1)  2957, 2857, 1641, 1593, 1549, 1487, 1446, 1423, 1257, 1117, 780. Data collection Diffractometer Absorption correction Tmin, Tmax No. of measured, independent and observed [I > 2(I)] reflections Rint (sin /)max (Å1) Refinement R[F 2 > 2(F 2)], wR(F 2), S No. of reflections No. of parameters H-atom treatment
max,
min (e Å3) Absolute structure Absolute structure parameter Bruker SMART CCD area detector Multi-scan (SADABS; Bruker, 2008) 0.658, 0.746 10022, 3282, 2995 0.036 0.617 0.041, 0.096, 1.07 3282 235 H-atom parameters constrained 0.21, 0.17 Flack x determined using 1105 quotients [(I+)(I)]/[(I+)+(I)] (Parsons et al., 2013) 0.05 (3) Computer programs: SMART and SAINT (Bruker, 2008), SHELXS97 and SHELXTL (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2015), Mercury (Macrae et al., 2008) and PLATON (Spek, 2009). Refinement Crystal data, data collection and structure refinement details are summarized in Table 2. Funding information Funding for this research was provided by: Shanghai Municipal Education Commission of China; Shanghai University of Engineering Science (award No. 1–5300-16–020113). References Figure 2 A view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1). 2 of 3 Sun et al.  C17H16ClN5O3 Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Fershtat, L. L., Kulikov, A. S., Ananyev, I. V., Struchkova, M. I. & Makhova, N. N. (2016). J. Heterocycl. Chem. 53, 102–108. IUCrData (2017). 2, x170370 data reports Gan, X. H., Hu, D. H., Li, P., Wu, J., Chen, X., Xue, W. & Song, B. (2016). Pest. Manag. Sci. 72, 534–543. Li, D.-J., Zhang, J.-B. & Fu, H.-G. (2005). Chin. J. Synth. Chem. 13, 361–363. Liu, J. C., Wang, W. D. & He, H. W. (2014). Chin. J. Org. Chem. 37, 1447–1451. Luqman, A., Blair, V. L., Brammananth, R., Crellin, P. K., Coppel, R. L. & Andrews, P. C. (2015). Eur. J. Inorg. Chem. pp. 4935–4945. Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. IUCrData (2017). 2, x170370 Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249– 259. Pattison, G., Sandford, G., Yufit, D. S., Howard, J. A. K., Christopher, J. A. & Miller, D. D. (2009). J. Org. Chem. 74, 5533–5540. Shaikh, A. & Meshram, J. (2016). J. Heterocycl. Chem. 53, 1176– 1182. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Spek, A. L. (2009). Acta Cryst. D65, 148–155. Sun et al.  C17H16ClN5O3 3 of 3 data reports full crystallographic data IUCrData (2017). 2, x170370 [https://doi.org/10.1107/S2414314617003704] 4-Chloro-5-(morpholin-4 (...truncated)