Abstract
C14H14BrN3O3, orthorhombic, Pca21 (no. 29), a = 32.932(3) Å, b = 5.8490(7) Å, c = 7.3606(8) Å, V = 1417.8(3) Å3, Z = 4, Rgt(F) = 0.0260, wRref(F2) = 0.0553, T = 150 K.
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: | Colourless block |
| Size: | 0.13 × 0.12 × 0.10 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 2.91 mm−1 |
| Diffractometer, scan mode: | SuperNova, ω |
| θmax, completeness: | 25.0°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 8422, 2473, 0.032 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 2348 |
| N(param)refined: | 194 |
| Programs: | Bruker [1], Olex2 [2], SHELX [3], Diamond [4] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| Br1 | 0.51097 (2) | 0.38439 (7) | 0.72739 (9) | 0.03716 (15) |
| O1 | 0.67461 (8) | 0.7160 (4) | 0.4622 (4) | 0.0262 (6) |
| H1 | 0.692648 | 0.622504 | 0.481506 | 0.039* |
| O2 | 0.78571 (9) | 0.4150 (4) | 0.5381 (4) | 0.0240 (6) |
| N1 | 0.70558 (10) | 0.3172 (5) | 0.5857 (4) | 0.0202 (7) |
| N2 | 0.73580 (10) | 0.1605 (5) | 0.6187 (4) | 0.0233 (8) |
| H2 | 0.729854 | 0.025668 | 0.656964 | 0.028* |
| N3 | 0.80263 (10) | 0.0499 (5) | 0.6232 (4) | 0.0238 (7) |
| H3 | 0.792778 | −0.079701 | 0.656494 | 0.029* |
| C1 | 0.63868 (13) | 0.6347 (6) | 0.5286 (5) | 0.0193 (8) |
| C2 | 0.60427 (12) | 0.7719 (6) | 0.5056 (5) | 0.0220 (9) |
| H2A | 0.606793 | 0.913742 | 0.449679 | 0.026* |
| C3 | 0.56676 (12) | 0.6998 (7) | 0.5645 (5) | 0.0228 (9) |
| H3A | 0.544076 | 0.792307 | 0.548176 | 0.027* |
| C4 | 0.56291 (12) | 0.4883 (6) | 0.6485 (5) | 0.0220 (9) |
| C5 | 0.59657 (12) | 0.3501 (6) | 0.6724 (4) | 0.0197 (9) |
| H5 | 0.593559 | 0.208760 | 0.728769 | 0.024* |
| C6 | 0.63526 (12) | 0.4193 (6) | 0.6132 (5) | 0.0181 (8) |
| C7 | 0.66957 (12) | 0.2649 (6) | 0.6383 (5) | 0.0184 (8) |
| H7 | 0.665247 | 0.124258 | 0.694014 | 0.022* |
| C8 | 0.77559 (12) | 0.2212 (6) | 0.5898 (5) | 0.0199 (8) |
| C9 | 0.84558 (12) | 0.0651 (6) | 0.6084 (5) | 0.0211 (8) |
| C10 | 0.86736 (12) | 0.2567 (6) | 0.6646 (4) | 0.0202 (9) |
| H10 | 0.853603 | 0.385403 | 0.705996 | 0.024* |
| C11 | 0.90932 (13) | 0.2564 (7) | 0.6592 (5) | 0.0257 (9) |
| H11 | 0.923584 | 0.384325 | 0.698650 | 0.031* |
| C12 | 0.93050 (13) | 0.0662 (7) | 0.5954 (5) | 0.0295 (10) |
| H12 | 0.958723 | 0.066914 | 0.591294 | 0.035* |
| C13 | 0.90894 (14) | −0.1236 (7) | 0.5381 (5) | 0.0276 (10) |
| H13 | 0.922824 | −0.251318 | 0.495698 | 0.033* |
| C14 | 0.86663 (13) | −0.1254 (6) | 0.5433 (5) | 0.0230 (9) |
| H14 | 0.852420 | −0.253328 | 0.503507 | 0.028* |
| O3 | 0.75611 (9) | 0.7192 (4) | 0.2769 (3) | 0.0272 (7) |
| H3B | 0.766837 | 0.640466 | 0.361224 | 0.041* |
| H3C | 0.747314 | 0.620749 | 0.201607 | 0.041* |
Source of material
A mixture of 0.1005 g 5-bromosalicylaldehyde (0.5 mmol) and 0.0756 g 4-phenylsemicarbazide (0.5 mmol) in ethanol (10 mL) was stirred at room temperature. After 0.5 h, 2 mL water solution of 0.0595 g calcium perchlorate hydrate (0.25 mmol) was added. The reaction mixture was continully stirred for 3 h at 70 °C and cooled to room temperature. The reactant was filtered to a small flask. The colorless crystals of the title compound were obtained by slow evaporation in 20 days.
Experimental details
The hydrogen atoms were positioned geometrically (C-H = 0.93 Å, N-H = 0.86 Å and O-H = 0.82 Å). Their Uiso values were set to 1.2Ueq or 1.5Ueq of the parent atoms.
Comment
Some hydrazone compounds and their metal complex have found considerable applications in catalysis [5], anticancer and antimicrobial activities [6], [7], as well as electrochemical sensors [8]. Our research group has been devoted to the study of hydrazone compounds [9], [10], [11]. We wanted to synthesize a Ca(II) complex with (E)-2-(5-bromo-2-hydroxybenzylidene)-N-phenylhydrazine-1-carboxamide, however, the Ca(II) does not take part in coordination. Only a new hydrazone compound has been obtained.
The molecular structure of the title compound is depicted in the Figure. The compound consists of one (E)-2-(5-bromo-2-hydroxybenzylidene)-N-phenylhydrazine-1-carboxamide molecule and one water molecule. The bond distances of C-N are 1.284(5) Å (C7-N1), 1.374(5) Å (C8-N2) and 1.421(5) Å (C9-N3), respectively. The bond distance of C7-N1 is shorter than those of C8-N2 and C9-N3, indicating the C7-N1 bond is a double bond. The dihedral angle between plane 1 (C1-C2-C3-C4-C5-C6) and plane 2 (C9-C10-C11-C12-C13-C14) is 47.8°. In the crystal packing, the hydrazone molecules form a 3D network by intermolecular N-H…O, O-H…N and O-H…O hydrogen bonds.
Funding source: National Natural Science Foundation of China
Award Identifier / Grant number: 21171132
Funding source: Natural Science Foundation of Shandong
Award Identifier / Grant number: ZR2014BL003
Funding source: Shandong Province Higher Educational Science and Technology Program
Award Identifier / Grant number: J14LC01
Funding source: Science Foundation of Weifang
Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: This project was supported by the National Natural Science Foundation of China (No. 21171132), the Natural Science Foundation of Shandong (ZR2014BL003), the project of Shandong Province Higher Educational Science and Technology Program (J14LC01) and Science Foundation of Weifang.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Bruker. SAINT and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2000.Search in Google Scholar
2. 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. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar
3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar
4. Brandenburg, K. DIAMOND. Visual Crystal Structure Information System. Ver. 4.0; Crystal Impact: Bonn, Germany, 2015.Search in Google Scholar
5. Taghizadeh, M.-J., Karimi, H., Mirzaie, A. Zeolite-encapsulated Mn(II) complex: a new nano catalyst for the synthesis of modafinil and its derivatives. Lett. Org. Chem. 2019, 16, 541–549; https://doi.org/10.2174/1570178615666180622123944.Search in Google Scholar
6. Muluk, M.-B., Dhumal, S.-T., Rehman, N.-N.-M.-A., Dixit, P.-P., Kharat, K.-R., Haval, K.-P. Synthesis, anticancer and antimicrobial evaluation of new (E)--benzylidene-2-(2-ethylpyridin-4- yl)-4-methylthiazole-5-carbohydrazides. ChemistrySelect 2019, 4, 8993–8997; https://doi.org/10.1002/slct.201902030.Search in Google Scholar
7. Aradhyula, B.-P.-R., Joshi, N., Poluri, K.-M., Kollipara, M.-R. Synthesis and antibacterial studies of rhodium and iridium complexes comprising of dipyridyl hydrazones. J. Mol. Struct. 2018, 1164, 191–199; https://doi.org/10.1016/j.molstruc.2018.03.058.Search in Google Scholar
8. Ling, L., Hu, J.-F., Zhang, H. Ferrocene containing N-tosyl hydrazones as optical and electrochemical sensors for Hg2+, Cu2+ and F− ions. Tetrahedron 2019, 75, 2472–2481; https://doi.org/10.1016/j.tet.2019.03.023.Search in Google Scholar
9. Tai, X.-S., Meng, Q.-G., Liu, L.-L. Synthesis, crystal structure, and cytotoxic activity of a novel eight-coordinated dinuclear Ca(II)-schiff base complex. Crystals 2016, 6, 109; https://doi.org/10.3390/cryst6090109.Search in Google Scholar
10. Tai, X.-S., Wang, L.-H, Liu, L.-L., Zhou, X.-J. The crystal structure of (E)-N′-((2-hydroxynaphthalen-1-yl)methylene)- 2-phenylacetohydrazide. C19H16O2N2. Z. Kristallogr. NCS 2019, 234, 723–724. https://doi.org/10.1515/ncrs-2019-0074.Search in Google Scholar
11. Tai, X.-S., Li, P.-F. The crystal structure (E)-4-methyl-N′-(2-nitrobenzylidene)benzenesulfonohydrazide, C14H13N3O4S. Z. Kristallogr. NCS 2017, 232, 1031–1032. https://doi.org/10.1515/ncrs-2017-0166.Search in Google Scholar
© 2020 Wang Li-Hua et al., published by De Gruyter, Berlin/Boston
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