Abstract
C15H24N2O4, orthorhombic, Pca21, a = 18.528(6) Å, b = 8.123(2) Å, c = 20.797(6) Å, V = 3129.9(16) Å3, Z = 8, Rgt(F) = 0.0396, wRref(F2) = 0.1082, T = 296(2) K.
The organic cation of the title 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 |
| Size: | 0.34 × 0.32 × 0.30 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 0.09 mm−1 |
| Diffractometer, scan mode: | Bruker APEX-II CCD, φ & ω |
| θmax: | 25.0° |
| N(hkl)measured, N(hkl)unique, Rint: | 28099, 5520, 0.030 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 5009 |
| N(param)refined: | 389 |
| Programs: | SAINT [6], SHELX [7] OLEX2 [8] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| C1 | −0.11258(11) | −1.5999(3) | −0.18701(11) | 0.0364(5) |
| N1 | −0.27117(10) | −1.5313(2) | −0.04469(9) | 0.0425(4) |
| O1 | −0.17877(8) | −1.4237(2) | −0.25550(8) | 0.0425(4) |
| C2 | −0.17327(11) | −1.4951(2) | −0.19980(10) | 0.0320(4) |
| H2 | −0.0920 | −1.5012 | −0.3010 | 0.041* |
| H2A | 0.1309 | −1.5852 | −0.2654 | 0.062* |
| N2 | −0.05562(8) | −1.5602(2) | −0.28971(9) | 0.0344(4) |
| O2 | 0.09973(8) | −1.51574(19) | −0.25843(8) | 0.0415(4) |
| C3 | −0.22536(11) | −1.4750(3) | −0.15125(11) | 0.0350(5) |
| H3 | −0.0126 | −1.9519 | −0.3672 | 0.073* |
| H3A | −0.2646 | −1.4068 | −0.1593 | 0.042* |
| N3 | −0.51140(10) | −1.0872(2) | −0.60567(9) | 0.0428(4) |
| O3 | −0.02868(8) | −1.86377(18) | −0.35428(9) | 0.0487(4) |
| C4 | −0.22084(11) | −1.5527(3) | −0.09173(10) | 0.0363(5) |
| H4 | −0.3556 | −0.9047 | −0.3462 | 0.039* |
| H4A | −0.0240 | −1.2911 | −0.3960 | 0.079* |
| N4 | −0.31754(8) | −0.9635(2) | −0.35184(9) | 0.0328(4) |
| O4 | −0.05638(9) | −1.3596(2) | −0.39843(10) | 0.0530(4) |
| C5 | −0.15992(13) | −1.6587(3) | −0.08054(12) | 0.0513(6) |
| H5 | −0.1554 | −1.7137 | −0.0415 | 0.062* |
| O5 | −0.44725(8) | −0.87590(17) | −0.39983(8) | 0.0375(3) |
| C6 | −0.10954(12) | −1.6786(3) | −0.12625(12) | 0.0487(6) |
| H6 | −0.2571 | −1.3263 | −0.2791 | 0.059* |
| H6A | −0.0707 | −1.7475 | −0.1176 | 0.058* |
| O6 | −0.29299(7) | −1.27128(17) | −0.28751(8) | 0.0393(3) |
| C7 | −0.32987(13) | −1.4129(3) | −0.05086(12) | 0.0452(5) |
| H7 | −0.1301 | −0.8676 | −0.3724 | 0.102* |
| H7A | −0.3138 | −1.3220 | −0.0775 | 0.054* |
| H7B | −0.3412 | −1.3692 | −0.0086 | 0.054* |
| O7 | −0.17393(9) | −0.8796(3) | −0.36954(11) | 0.0679(6) |
| C8 | −0.39777(14) | −1.4852(4) | −0.07984(16) | 0.0619(7) |
| H8 | −0.3523 | −0.6946 | −0.2371 | 0.077* |
| H8A | −0.3881 | −1.5205 | −0.1230 | 0.093* |
| H8B | −0.4351 | −1.4032 | −0.0803 | 0.093* |
| H8C | −0.4132 | −1.5777 | −0.0546 | 0.093* |
| O8 | −0.34396(9) | −0.7935(2) | −0.23962(9) | 0.0511(4) |
| C9 | −0.26939(13) | −1.6224(3) | 0.01574(12) | 0.0499(6) |
| H9A | −0.2472 | −1.7288 | 0.0083 | 0.060* |
| H9B | −0.3185 | −1.6415 | 0.0300 | 0.060* |
| C10 | −0.2288(3) | −1.5354(6) | 0.06820(16) | 0.0999(15) |
| H10A | −0.1816 | −1.5057 | 0.0529 | 0.150* |
| H10B | −0.2242 | −1.6070 | 0.1047 | 0.150* |
| H10C | −0.2545 | −1.4378 | 0.0805 | 0.150* |
| C11 | −0.05792(11) | −1.6256(3) | −0.23215(11) | 0.0377(5) |
| H11 | −0.0201 | −1.6946 | −0.2204 | 0.045* |
| C12 | 0.00268(10) | −1.5775(3) | −0.33657(10) | 0.0355(5) |
| C13 | 0.06697(11) | −1.4690(3) | −0.31726(12) | 0.0382(5) |
| H13A | 0.1030 | −1.4734 | −0.3511 | 0.046* |
| H13B | 0.0507 | −1.3559 | −0.3138 | 0.046* |
| C14 | 0.02878(11) | −1.7555(3) | −0.34138(13) | 0.0414(5) |
| H14A | 0.0644 | −1.7641 | −0.3754 | 0.050* |
| H14B | 0.0517 | −1.7869 | −0.3013 | 0.050* |
| C15 | −0.02615(13) | −1.5184(3) | −0.40131(13) | 0.0462(5) |
| H15A | 0.0129 | −1.5184 | −0.4323 | 0.055* |
| H15B | −0.0626 | −1.5951 | −0.4163 | 0.055* |
| C16 | −0.36061(11) | −1.0352(3) | −0.45735(10) | 0.0358(5) |
| C17 | −0.42964(11) | −0.9559(2) | −0.45191(10) | 0.0315(4) |
| C18 | −0.47793(11) | −0.9722(3) | −0.50326(10) | 0.0352(5) |
| H18 | −0.5218 | −0.9167 | −0.5013 | 0.042* |
| C19 | −0.46293(11) | −1.0683(3) | −0.55738(10) | 0.0370(5) |
| C20 | −0.39450(12) | −1.1496(3) | −0.56101(11) | 0.0461(6) |
| H20 | −0.3832 | −1.2148 | −0.5964 | 0.055* |
| C21 | −0.34645(12) | −1.1308(3) | −0.51272(11) | 0.0459(6) |
| H21 | −0.3020 | −1.1831 | −0.5161 | 0.055* |
| C22 | −0.57628(13) | −0.9872(3) | −0.60904(13) | 0.0488(6) |
| H22A | −0.5881 | −0.9691 | −0.6539 | 0.059* |
| H22B | −0.5660 | −0.8806 | −0.5901 | 0.059* |
| C23 | −0.64085(15) | −1.0583(4) | −0.57631(18) | 0.0688(8) |
| H23A | −0.6542 | −1.1594 | −0.5970 | 0.103* |
| H23B | −0.6802 | −0.9818 | −0.5788 | 0.103* |
| H23C | −0.6296 | −1.0796 | −0.5320 | 0.103* |
| C24 | −0.49889(13) | −1.1982(3) | −0.66007(11) | 0.0469(5) |
| H24A | −0.5451 | −1.2346 | −0.6768 | 0.056* |
| H24B | −0.4731 | −1.2946 | −0.6449 | 0.056* |
| C25 | −0.4566(2) | −1.1203(4) | −0.71354(15) | 0.0698(9) |
| H25A | −0.4463 | −1.2014 | −0.7458 | 0.105* |
| H25B | −0.4122 | −1.0771 | −0.6968 | 0.105* |
| H25C | −0.4843 | −1.0326 | −0.7322 | 0.105* |
| C26 | −0.30988(11) | −1.0348(2) | −0.40741(11) | 0.0362(5) |
| H26 | −0.2668 | −1.0906 | −0.4147 | 0.043* |
| C27 | −0.26658(10) | −0.9752(2) | −0.29812(10) | 0.0354(5) |
| C28 | −0.28930(12) | −1.1203(3) | −0.25488(11) | 0.0379(5) |
| H28A | −0.2550 | −1.1302 | −0.2198 | 0.045* |
| H28B | −0.3362 | −1.0964 | −0.2364 | 0.045* |
| C29 | −0.18939(11) | −0.9996(3) | −0.32215(13) | 0.0460(6) |
| H29A | −0.1558 | −0.9891 | −0.2866 | 0.055* |
| H29B | −0.1842 | −1.1090 | −0.3403 | 0.055* |
| C30 | −0.27238(12) | −0.8177(3) | −0.25927(12) | 0.0450(5) |
| H30A | −0.2413 | −0.8245 | −0.2219 | 0.054* |
| H30B | −0.2567 | −0.7251 | −0.2852 | 0.054* |
Source of material
A mixture of Tris(hydroxymethyl)methyl aminomethane (1.21 g, 10 mmol) and 4-diethylaminosalicylaldehyde (1.93 g, 10 mmol), in anhydrous ethanol (30 mL) was heated at 373 K for about 3 h. Then the solvent was removed under reduced pressure. The resulting residue was purified by recrystallization from ethanol to obtain a crystal.
Experimental details
All hydrogen atoms were introduced by a riding model. The methyl groups were idealized and refined using rigid groups allowed to rotate about the N—C bond (AFIX 137 option of the SHELXL-2013 program) [7]. The Uiso values of the hydrogen atoms of the methyl groups were set to 1.5Ueq(C) and the Uiso values of all other hydrogen atons were set to 1.2Ueq(C).
Discussion
o-Hydroxy Schiff bases belong to an important class of organic compounds due to their crystallography and biological activity [1], [2], [3], [4], [5]. From the crystallography point of view, o-hydroxy Schiff-bases are of great interest to the investigators mostly due to the intramolecular H-bond.
The asymmetric unit of the title compound contains two molecules. One of them is shown in the figure. Their geometric parameters are very similar. They both are in the zwitterionic form in the solid state, with the H atom of the phenol group being transferred to the imine N atom. Consequently, they both adopt an E-configuration about the central C = N double bond.
In both molecules an intramolecular NH⋯O hydrogen bond is present. Adjacent molecules are connected via classical NH⋯O hydrogen bonds to form a 2D network parallel to the ab plane.
Acknowledgement
This work was financially supported by the Scientific Research Fund of Hunan Provincial Education Department (No. 16B104), Natural Science Foundation of Hunan Province of China (2017JJ3093), the Opening Project of Key Laboratory of Comprehensive Utilization of Advantage Plants Resources in Hunan South (No. XNZW16C01) and the Scientific Research Fund of Hunan University of Science and Engineering (No. 16XKY063).
References
Xu, T. T.; Xu, X. Y.; Gao, J.; Liu, L. L.; Ni, S. S.; Lu, L. D.; Yang, X. J.: Thermoelectric properties of Bi2Te3 atomic quintuple thin films. Chinese J. Struct. Chem. 25 (2006) 1502–1506.Search in Google Scholar
Hopfl, H.; Sanchea, M.; Barba, V.; Farfan, N.; Rojas, S.; Santillan, R.: Synthesis and study of monomeric and dimeric boronates by spectroscopic methods and X-ray crystallography. Inorg. Chem. 37 (1998) 1679–1681.10.1021/ic970886gSearch in Google Scholar
Fulop, F.; Sillanpaa, R.; Dahlqvist, M.; Pihlaja, K.; Vainiotalo, P.: Ring-chain tautomerism and crystal structure of some 1,3-oxazacyclanes, and the electrophilic substitutent constants for some heteroaryl groups in solution and in the gas-phase. Heterocycles 37 (1994) 1093–1095.10.3987/COM-93-S121Search in Google Scholar
Zhao, S. J.; Yuan, J.: Recognizing the importance of ADR monitoring of drugs available on the market from PPA event. China Pharm. 9 (2001) 551–552.Search in Google Scholar
Kerman, W. N.; Viscolij, C. M.; Brassj, L. M.; Broderick, J. P.; Brott, T.; Feldmanna, E.: Drug interactions in geriatric patients. Adverse Drug React. 1 (2001) 10–17.10.1007/BF03264506Search in Google Scholar
SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.Search in Google Scholar
Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed
Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H.: OLEX2: A complete structure solution, refinement and analysis program. J. Appl. Cryst. 42 (2009) 339–341.10.1107/S0021889808042726Search in Google Scholar
©2017 Lin Yuan et al., published by De Gruyter, Berlin/Boston
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