Crystal structure of (E)-1-(3-((E)-((2-hydroxy

Z. Kristallogr. NCS 2017; aop

Open Access Yan-Bin Wang* and Qiong Su

Crystal structure of (E)-1-(3-((E)-((2-hydroxynaphthalen-1-yl)methylene)amino)phenyl) ethanone O-benzyl oxime, C26H22N2O2 Table 1: Data collection and handling. Crystal: Size: Wavelength: µ: Diffractometer, scan mode: 2θmax , completeness: N(hkl)measured , N(hkl)unique , Rint : Criterion for Iobs , N(hkl)gt : N(param)refined : Programs:

Yellow block 0.34 × 0.14 × 0.10 mm Mo Kα radiation (0.71073 Å) 0.8 cm−1 SuperNova Dual, ω scans 52°, >99% 7312, 3943, 0.063 Iobs > 2 σ(Iobs ), 1984 310 SHELX [1], CrysAlisPRO [2]

Source of materials DOI 10.1515/ncrs-2016-0387 Received January 4, 2017; accepted May 3, 2017; available online May 20, 2017

Abstract C26 H22 N2 O2 , monoclinic, P21 /c (no. 14), a = 21.8152(18) Å, b = 4.3629(2) Å, γ = 22.0099(12) Å, β = 106.951(6)°, V = 2003.8(2) Å3 , Z = 4, Rgt (F) = 0.0639, wRref (F 2 ) = 0.1555, T = 298(2) K. CCDC no.: 1546077 The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

*Corresponding author: Yan-Bin Wang, College of Chemical Engineering, Northwest University for Nationalities, Lanzhou 730030, P. R. China; and Key Laboratory for Utifity of Environmentfriendly Composite Materials and Biomass in Universities of Gansu Province, e-mail: [email protected] Qiong Su: College of Chemical Engineering, Northwest University for Nationalities, Lanzhou 730030, P. R. China; and Key Laboratory for Utifity of Environment-friendly Composite Materials and Biomass in Universities of Gansu Province

To a hot ethanolic solution (10 mL) of benzaldehyde (290.4 mg, 1 mmol) was added an ethanolic solution (5 mL) of (E)-1-(((3-(1-aminoethyl)phenyl)imino)methyl) naphthalen-2-ol (106.1 mg, 1.00 mmol). After the mixture had been stirred at 338 K for 4 h, the solvent was partially evaporated under reduced pressure. After cooling to room temperature, the mixture was filtered, washed successively with ethanol and hexane. The isolated compound was dried under reduced pressure to yield 302.1 mg of light yellow solid. Yield: 76.5%. m.p. 331–333 K. Block-shaped single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from an ethanolic solution at room temperature. Elemental analysis: Calcd. for C26 H22 N2 O2 [%]: C, 79.16; H, 5.62; N, 7.10; Found: C, 79.16; H, 5.62; N, 7.10.

Experimental details Molecular structure was refined using the SHELX package. Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms. There is a disorder of the phenyl group.

Comment Oxime-type compounds and their derivatives play an important role in the development of coordination chemistry [3– 7], because they can accommodate one, two or more metal centers and form homo- and heteronuclear metal complexes

© 2017 Yan-Bin Wang et al., published by De Gruyter. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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2 | Wang and Su: C26 H22 N2 O2

Table 2: Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2 ). Atom N1 O1 H1 O2 C11 H11 C9 C10 C4 C17 H17 C12 C7 H7 N2 C16 C8 H8 C3 H3 C6 H6 C2 H2 C1 C21 C18 C13 H13 C5 H5 C15 H15 C14 H14 C24 H24a H24Aa C20 H20A H20B C19 H19A H19B H19C C26a H26a C26′a H26′a C25a H25a C22a H22a C23a H23a

x

y

z

Uiso */Ueq

0.10605(17) 0.02905(14) 0.0420 0.34938(15) 0.1495(2) 0.1903 0.1856(2) 0.13720(19) 0.1705(2) 0.1829(2) 0.2150 0.1223(2) 0.2917(2) 0.3325 0.28790(17) 0.1964(2) 0.2481(2) 0.2594 0.1090(2) 0.0992 0.2770(2) 0.3072 0.0640(2) 0.0243 0.0770(2) 0.4411(2) 0.2605(2) 0.0747(2) 0.0337 0.2166(2) 0.2062 0.1483(2) 0.1567 0.0880(2) 0.0561 0.5673(3) 0.6102 0.6094 0.3727(2) 0.3466 0.3707 0.2897(3) 0.3301 0.2615 0.2962 0.4875(5) 0.4758 0.4688(5) 0.4454 0.5495(6) 0.5793 0.4598(6) 0.4298 0.5223(5) 0.5340

0.1082(8) −0.0204(7) 0.0658 0.9255(8) −0.0493(10) −0.0604 −0.3908(9) −0.2081(9) −0.5433(10) 0.4023(10) 0.3665 0.2772(9) −0.6147(10) −0.6364 0.7942(9) 0.5795(10) −0.4389(10) −0.3472 −0.5039(10) −0.6008 −0.7651(11) −0.8878 −0.3267(10) −0.2998 −0.1830(10) 1.1474(12) 0.7239(10) 0.3352(10) 0.2576 −0.7258(11) −0.8224 0.6304(10) 0.7470 0.5052(10) 0.5368 1.3328(14) 1.3810 1.4006 1.0456(14) 1.2179 0.8894 0.7842(13) 0.6799 0.7107 1.0005 1.077(3) 0.9635 1.319(3) 1.3779 1.180(3) 1.1440 1.322(3) 1.3796 1.417(3) 1.5387

0.47091(17) 0.36222(15) 0.3967 0.62052(14) 0.4551(2) 0.4837 0.38058(19) 0.39532(19) 0.3206(2) 0.5546(2) 0.5353 0.5279(2) 0.4054(2) 0.4336 0.59236(17) 0.6093(2) 0.4221(2) 0.4619 0.2768(2) 0.2375 0.3464(2) 0.3358 0.2914(2) 0.2616 0.3511(2) 0.5997(2) 0.6344(2) 0.5575(2) 0.5399 0.3049(2) 0.2655 0.6388(2) 0.6756 0.6122(2) 0.6318 0.6474(3) 0.6661 0.6631 0.5710(2) 0.5508 0.5391 0.7038(2) 0.7183 0.7268 0.7107 0.5672(5) 0.5299 0.5665(5) 0.5257 0.5917(6) 0.5697 0.6525(5) 0.6729 0.6766(5) 0.7129

0.0346(9) 0.0445(9) 0.067* 0.0454(9) 0.0352(11) 0.042* 0.0300(10) 0.0293(10) 0.0341(11) 0.0335(10) 0.040* 0.0332(10) 0.0397(12) 0.048* 0.0400(10) 0.0334(10) 0.0372(11) 0.045* 0.0389(11) 0.047* 0.0445(12) 0.053* 0.0408(12) 0.049* 0.0342(11) 0.0446(12) 0.0372(11) 0.0403(12) 0.048* 0.0418(12) 0.050* 0.0382(11) 0.046* 0.0419(12) 0.050* 0.0630(16) 0.076* 0.076* 0.0572(15) 0.069* 0.069* 0.0588(15) 0.088* 0.088* 0.088* 0.048(3) 0.057* 0.060(3) 0.072* 0.064(3) 0.077* 0.056(3) 0.067* 0.064(3) 0.077*

Table 2 (continued) Atom

x

y

z

Uiso */Ueq

a

0.5320(6) 0.5496 0.4770(5) 0.4578 0.5402(5) 0.5648

1.416(3) 1.5415 1.052(3) 0.9318 1.137(3) 1.0693

0.5903(7) 0.5656 0.6614(5) 0.6857 0.6852(5) 0.7249

0.067(3) 0.080* 0.065(4) 0.078* 0.058(3) 0.069*

C25′ H25′a C22′a H22′a C23′a H23′a

[8–12]. Moreover, oxime-type compounds and its metal complexes studied by the group of W. K. Dong have a significant application in the fields of luminescence and magnetic materials, catalysis and supramolecular chemistry [13–16]. The crystal structure is only built up from C26 H22 N2 O2 molecules, in which all bond lengths are in normal ranges. The aryl ring (C12—C17) and the naphthyl moiety form a dihedral angle of 34.82(11)°. In addition, there is a strong intramolecular O—H· · · N hydrogen bond interaction between the hydroxyl (O1—H1) group and the Schiff base nitrogen (N1) atom, with the distance of d(N1· · · O1) = 2.552(3) Å [17].

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Wang and Su: C26 H22 N2 O2

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