Abstract
C26H22N2O, orthorhombic, Pca21 (no. 29), a = 22.8108(10) Å, b = 9.8328(5) Å, c = 8.7361(3) Å, V = 1959.45(15) Å3, Z = 4, Rgt(F) = 0.0380, wRref(F2) = 0.0853, 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.
Crystal: | Prism, yellow |
Size: | 0.30 × 0.20 × 0.10 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 0.08 mm−1 |
Diffractometer, scan mode: | Bruker APEX-II, φ and ω-scans |
θmax, completeness: | 27.5°, >99% |
N(hkl)measured, N(hkl)unique, Rint: | 16967, 4302, 0.032 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 3502 |
N(param)refined: | 263 |
Programs: | Bruker programs [1], SHELX [2] |
Atom | x | y | z | Uiso*/Ueq |
---|---|---|---|---|
O1 | 0.55088(6) | 0.36772(15) | 0.3663(2) | 0.0551(4) |
N1 | 0.59179(6) | 0.54488(17) | 0.48472(19) | 0.0401(4) |
N2 | 0.64092(6) | 0.60582(16) | 0.5498(2) | 0.0403(4) |
C1 | 0.31521(9) | 0.5039(3) | 0.4510(3) | 0.0530(6) |
H1 | 0.2763 | 0.4779 | 0.4623 | 0.064* |
C2 | 0.32933(9) | 0.6057(2) | 0.3558(3) | 0.0505(6) |
H6 | 0.3000 | 0.6476 | 0.2989 | 0.061* |
C3 | 0.38881(8) | 0.6513(2) | 0.3398(2) | 0.0398(5) |
C4 | 0.43351(8) | 0.59116(19) | 0.4338(2) | 0.0364(4) |
C5 | 0.49121(8) | 0.64482(19) | 0.4290(2) | 0.0346(4) |
C6 | 0.53561(8) | 0.59865(19) | 0.5479(2) | 0.0379(4) |
H20 | 0.5175 | 0.5275 | 0.6107 | 0.045* |
C7 | 0.55791(8) | 0.7119(2) | 0.6547(2) | 0.0422(5) |
H14 | 0.5447 | 0.8006 | 0.6204 | 0.051* |
H13 | 0.5448 | 0.6974 | 0.7590 | 0.051* |
C8 | 0.62343(8) | 0.6992(2) | 0.6425(2) | 0.0384(4) |
C9 | 0.66533(8) | 0.7843(2) | 0.7266(2) | 0.0407(5) |
C10 | 0.72473(9) | 0.7533(2) | 0.7305(3) | 0.0547(6) |
H12 | 0.7388 | 0.6793 | 0.6755 | 0.066* |
C11 | 0.76290(10) | 0.8313(3) | 0.8153(3) | 0.0657(7) |
H9 | 0.8025 | 0.8087 | 0.8186 | 0.079* |
C12 | 0.74290(12) | 0.9428(3) | 0.8953(3) | 0.0671(7) |
H2 | 0.7689 | 0.9955 | 0.9517 | 0.081* |
C13 | 0.53033(11) | 0.9518(2) | 0.1021(3) | 0.0583(6) |
H3 | 0.5390 | 1.0182 | 0.0298 | 0.070* |
C14 | 0.47572(11) | 0.9005(2) | 0.1118(3) | 0.0544(6) |
H4 | 0.4470 | 0.9318 | 0.0450 | 0.065* |
C15 | 0.46086(9) | 0.7997(2) | 0.2218(2) | 0.0411(5) |
C16 | 0.40369(9) | 0.7520(2) | 0.2366(3) | 0.0456(5) |
H5 | 0.3746 | 0.7891 | 0.1749 | 0.055* |
C17 | 0.35954(9) | 0.4366(2) | 0.5340(3) | 0.0504(5) |
H7 | 0.3499 | 0.3622 | 0.5946 | 0.060* |
C18 | 0.41620(8) | 0.4787(2) | 0.5268(2) | 0.0431(5) |
H8 | 0.4444 | 0.4331 | 0.5839 | 0.052* |
C19 | 0.68446(12) | 0.9758(3) | 0.8916(3) | 0.0661(7) |
H10 | 0.6708 | 1.0513 | 0.9450 | 0.079* |
C20 | 0.64577(10) | 0.8962(2) | 0.8081(3) | 0.0536(6) |
H11 | 0.6061 | 0.9183 | 0.8069 | 0.064* |
C21 | 0.59545(9) | 0.4259(2) | 0.4060(2) | 0.0418(5) |
C22 | 0.65663(9) | 0.3746(2) | 0.3703(3) | 0.0489(5) |
H18 | 0.6778 | 0.4437 | 0.3136 | 0.059* |
H19 | 0.6775 | 0.3584 | 0.4653 | 0.059* |
C23 | 0.65507(12) | 0.2444(3) | 0.2775(4) | 0.0711(8) |
H15 | 0.6338 | 0.1761 | 0.3329 | 0.107* |
H16 | 0.6944 | 0.2136 | 0.2594 | 0.107* |
H17 | 0.6360 | 0.2612 | 0.1814 | 0.107* |
C24 | 0.50527(8) | 0.74748(19) | 0.3226(2) | 0.0361(4) |
C25 | 0.56251(9) | 0.8059(2) | 0.3072(2) | 0.0428(5) |
H21 | 0.5924 | 0.7758 | 0.3710 | 0.051* |
C26 | 0.57434(10) | 0.9039(2) | 0.2024(3) | 0.0522(6) |
H22 | 0.6119 | 0.9401 | 0.1964 | 0.063* |
Source of materials
The title compound were synthesized by using previously reported protocol [3, 4] . A mixture of acetophenone (1.2 g, 9.9 mmol), 9-anthraldehyde (2.06 g, 9.9 mmol), and 3 M of aqueous sodium hydroxide (6 mL) in ethanol (20 mL) was stirred at room temperature for 8 h. The resulting solid was filtered to afford 3-(anthracen-9-yl)-1-phenylprop-2-en-1-one (chalcone), which was used without further purification. Then chalcone (1.2 g) and 3.5 g of an aqueous solution of hydrazine (80%) were dissolved in 20 mL of propionic acid. The mixture was then stirred at 120 °C for 5 h, and the resulting solution was cooled to room temperature and poured into ice water slowly. The crude product was collected by filtration and recrystallized from ethyl acetate to give pure product as yellow shaped crystals prism: 0.71 g, yield: 48.2%. Crystals were obtained by slow evaporation from methanol or ethanol at room temperature.
Experimental details
Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.
Comment
Anthracene derivatives have been playing an important role in the development of material chemistry [5], [6], [7], due to their excellent optical-physical properties [8, 9] . The title compound crystalizes in the orthorhombic and non-centrosymmetric space group Pca21, with one independent molecule in the asymmetric unit. The molecule shows a twisted structure, in which the pyrazoline ring and anthracene ring are approximately perpendicular (86.2°). The S-enantiomers are linked by weak CH⋯O hydrogen bond (C⋯O = 3.188(1) Å) to construct a helical chain motif, which are in accord with the literature [10]; the adjacent chains with opposite chirality associate alternately along the a axis to form the overall 3D structure.
Acknowledgements
This work was supported by The National Natural Science Foundation of China (No. 81403260), China Postdoctoral Science Foundation (No. 2014M551639), Natural Science Foundation of Jiangsu Province (No. BK20140493), Postdoctoral Funding in Jiangsu Province (No. 1401138C), The Provincial Natural Science Foundation of Jiangsu Province (China) (No. 17KJB360015), The Technical Project of Yangzhou City (YZ2017090).
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©2018 Pingting Zhu et al., published by De Gruyter, Berlin/Boston
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