Abstract
C18H19N3O5, orthorhombic, Pna21 (no. 33), a = 15.5675(12) Å, b = 17.0299(13) Å, c = 6.2644(5) Å, V = 1660.8(2) Å3, Z = 4, R gt (F) = 0.0322, wR ref (F2) = 0.0815, T = 296 K.
The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Red rod |
| Size: | 0.20 × 0.08 × 0.06 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 0.11 mm−1 |
| Diffractometer, scan mode: | φ and ω |
| θmax, completeness: | 25.0°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 8219, 2626, 0.029 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 2161 |
| N(param)refined: | 235 |
| Programs: | SHELX [1], Bruker [2] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| C1 | −0.1590 (3) | 0.04232 (18) | −0.9933 (7) | 0.0715 (11) |
| H1A | −0.1490 | 0.0794 | −1.1081 | 0.086* |
| H1B | −0.2192 | 0.0453 | −0.9546 | 0.086* |
| C2 | −0.1391 (2) | −0.03934 (17) | −1.0713 (5) | 0.0522 (8) |
| H2A | −0.1749 | −0.0520 | −1.1932 | 0.063* |
| H2B | −0.0794 | −0.0427 | −1.1151 | 0.063* |
| C3 | −0.10359 (19) | −0.07264 (16) | −0.7100 (5) | 0.0472 (7) |
| H3A | −0.0430 | −0.0770 | −0.7445 | 0.057* |
| H3B | −0.1159 | −0.1081 | −0.5927 | 0.057* |
| C4 | −0.1240 (2) | 0.01038 (16) | −0.6449 (6) | 0.0584 (9) |
| H4A | −0.1837 | 0.0137 | −0.6020 | 0.070* |
| H4B | −0.0888 | 0.0249 | −0.5234 | 0.070* |
| C5 | −0.15175 (17) | −0.17567 (15) | −0.9530 (4) | 0.0378 (7) |
| C6 | −0.10748 (19) | −0.20433 (18) | −1.1289 (5) | 0.0474 (8) |
| H6 | −0.0774 | −0.1698 | −1.2164 | 0.057* |
| C7 | −0.10772 (19) | −0.28347 (18) | −1.1752 (6) | 0.0559 (8) |
| H7 | −0.0784 | −0.3018 | −1.2945 | 0.067* |
| C8 | −0.1508 (2) | −0.33542 (17) | −1.0470 (6) | 0.0559 (9) |
| H8 | −0.1492 | −0.3889 | −1.0769 | 0.067* |
| C9 | −0.19635 (19) | −0.30825 (16) | −0.8739 (5) | 0.0502 (8) |
| H9 | −0.2263 | −0.3434 | −0.7881 | 0.060* |
| C10 | −0.19777 (17) | −0.22911 (14) | −0.8269 (5) | 0.0381 (6) |
| C11 | −0.28100 (17) | −0.23456 (15) | −0.5014 (5) | 0.0394 (6) |
| H11 | −0.2725 | −0.2885 | −0.4913 | 0.047* |
| C12 | −0.32975 (16) | −0.19662 (14) | −0.3415 (5) | 0.0361 (6) |
| C13 | −0.34177 (16) | −0.11309 (15) | −0.3477 (5) | 0.0382 (7) |
| C14 | −0.38570 (17) | −0.07781 (14) | −0.1708 (5) | 0.0396 (6) |
| C15 | −0.41744 (17) | −0.12192 (15) | −0.0083 (5) | 0.0415 (7) |
| H15 | −0.4468 | −0.0983 | 0.1038 | 0.050* |
| C16 | −0.40541 (17) | −0.20394 (15) | −0.0114 (5) | 0.0386 (6) |
| C17 | −0.36341 (16) | −0.24092 (14) | −0.1716 (6) | 0.0397 (6) |
| H17 | −0.3569 | −0.2952 | −0.1693 | 0.048* |
| C18 | −0.4354 (3) | 0.04054 (18) | −0.0180 (7) | 0.0710 (11) |
| H18A | −0.4360 | 0.0960 | −0.0447 | 0.107* |
| H18B | −0.4934 | 0.0215 | −0.0097 | 0.107* |
| H18C | −0.4065 | 0.0303 | 0.1145 | 0.107* |
| O1 | −0.10863 (17) | 0.06372 (12) | −0.8156 (5) | 0.0723 (7) |
| O2 | −0.31332 (13) | −0.07093 (11) | −0.5016 (4) | 0.0504 (5) |
| O3 | −0.39176 (13) | 0.00174 (9) | −0.1863 (4) | 0.0528 (6) |
| O4 | −0.42169 (15) | −0.31982 (13) | 0.1722 (4) | 0.0667 (7) |
| O5 | −0.48221 (15) | −0.21685 (12) | 0.3016 (4) | 0.0631 (6) |
| N1 | −0.15568 (15) | −0.09447 (13) | −0.8973 (4) | 0.0397 (6) |
| N2 | −0.24779 (14) | −0.19745 (11) | −0.6608 (4) | 0.0382 (5) |
| H2 | −0.2573 | −0.1477 | −0.6662 | 0.046* |
| N3 | −0.43898 (16) | −0.24967 (15) | 0.1651 (5) | 0.0469 (6) |
Source of material
2-Hydroxy-3-methoxy-5-nitro-benzaldehyde (0.197 g, 1 mmol) and 2-morpholin-4-yl-phenylamine (0.178 g, 1 mmol) was dissolved in an ethanol solution (10 ml). The mixture was stirred for 1 h under refluxing. The resulting solution was left in air for a few days, yielding red rod-shaped crystals.
Experimental details
The structure was solved by Direct Methods and refined with the SHELX crystallographic software package [1]. The hydrogen atoms were placed at calculated positions and refined as riding atoms with isotropic displacement parameters.
Comment
Multidentate salen type salicylaldimine Schiff bases have attracted more and more attention in making complexes of transition and post-transition metals with different nuclearity [3]. Particularly, some of such metal complexes have been demontrated as potential cancer therapeutic agents. In addition, morpholine are proved to possess great pharmacological activity [4], and we have recently reported the structure of a morpholin-4-yl-containing Schiff base [5], namely quinolin-2-ylmethylene-(4-morpholin-4-yl-phenyl)amine. As part of our ongoing work, the title compound derived from 2-hydroxy-3-methoxy-5-nitro-benzaldehyde and 2-morpholin-4-yl-phenylamine was synthesized and characterized by X-ray diffraction.
In the title structure (see the figure), the bond lengths of C13–O2 and C11–N2 are found to be 1.281(3) and 1.293(4) Å, respectively, indicating the generated Schiff base existed in its tautomeric form, which is a common phenomenone in the case of some salicylaldimines [6]. Two benzene rings (C5–C10 and C12–C17, r.m.s. deviations of 0.0083 and 0.0065 Å, respectively) are almost coplanar, with the dihedral angle of 14.3°, showing a well conjugate effect between two rings, which should be contributed to the tautomerism of bridged imine bond. As expected, there exists an intramolecular N–H···O hydrogen bond in the structure (see the figure). Furthermore, a plenty of non-classical intermolecular C–H···O and intramolecular C–H···N hydrogen bonds are helpful to construct the solid structure.
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: Natural Science Foundation of Henan province (212300410348), Henan province key research and development and promotion special (212102310099), the Fundamental Research Funds for the Universities of Henan Province (NSFRF210343).
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
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