Abstract
C13H11ClN2O2S, orthorhombic, Pna21/n (no. 33), a = 33.781(4) Å, b = 5.2087(6) Å, c = 7.2979(8) Å, β = 90°, V = 1284.1(3) Å3, Z = 4, R gt (F) = 0.0429, wR ref (F2) = 0.1267, 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.
Crystal: | Yellow block |
Size: | 0.23 × 0.20 × 0.18 mm |
Wavelength: | MoKα radiation (0.71073 Å) |
μ: | 0.46 mm−1 |
Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
θmax, completeness: | 25.0°, >99% |
N(hkl)measured, N(hkl)unique, Rint: | 6160, 2235, 0.036 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 1794 |
N(param)refined: | 175 |
Programs: | Bruker [1], SHELX [2] |
Atom | x | y | Z | Uiso*/Ueq |
---|---|---|---|---|
C1 | 0.9810 (2) | 0.8480 (12) | −0.2536 (10) | 0.0548 (19) |
H1 | 0.999426 | 0.835520 | −0.347966 | 0.066* |
C2 | 0.95310 (19) | 1.0332 (12) | −0.2452 (9) | 0.0493 (17) |
H2 | 0.950049 | 1.158192 | −0.335087 | 0.059* |
C3 | 0.92900 (15) | 1.0200 (10) | −0.0878 (8) | 0.0317 (12) |
H3 | 0.908686 | 1.133749 | −0.059482 | 0.038* |
C4 | 0.94041 (15) | 0.8075 (10) | 0.0204 (8) | 0.0352 (13) |
C5 | 0.92251 (16) | 0.7127 (11) | 0.1901 (8) | 0.0363 (13) |
C6 | 0.85330 (16) | 0.9566 (10) | 0.5007 (8) | 0.0329 (12) |
C7 | 0.83529 (17) | 1.1750 (12) | 0.3945 (9) | 0.0453 (16) |
H7A | 0.851286 | 1.325874 | 0.409198 | 0.068* |
H7B | 0.809073 | 1.208206 | 0.439383 | 0.068* |
H7C | 0.834009 | 1.130062 | 0.267014 | 0.068* |
C8 | 0.83714 (16) | 0.8753 (11) | 0.6793 (8) | 0.0313 (13) |
C9 | 0.85195 (17) | 0.6599 (11) | 0.7735 (8) | 0.0363 (13) |
C10 | 0.83517 (18) | 0.5908 (11) | 0.9432 (9) | 0.0436 (15) |
H10 | 0.845315 | 0.450029 | 1.005952 | 0.052* |
C11 | 0.80461 (18) | 0.7239 (12) | 1.0179 (9) | 0.0440 (14) |
H11 | 0.793521 | 0.673025 | 1.128706 | 0.053* |
C12 | 0.79030 (15) | 0.9362 (10) | 0.9260 (9) | 0.0368 (13) |
C13 | 0.80551 (16) | 1.0129 (11) | 0.7604 (8) | 0.0340 (13) |
H13 | 0.795003 | 1.155584 | 0.701210 | 0.041* |
Cl1 | 0.75141 (5) | 1.1113 (3) | 1.0210 (3) | 0.0548 (5) |
N1 | 0.90097 (14) | 0.8956 (9) | 0.2811 (7) | 0.0406 (12) |
H1A | 0.898602 | 1.048873 | 0.238615 | 0.049* |
N2 | 0.88332 (13) | 0.8246 (8) | 0.4430 (7) | 0.0369 (11) |
O1 | 0.92519 (13) | 0.4914 (9) | 0.2437 (6) | 0.0507 (12) |
O2 | 0.88196 (13) | 0.5141 (8) | 0.7116 (6) | 0.0451 (11) |
H2A | 0.888517 | 0.563296 | 0.609249 | 0.068* |
S1 | 0.97918 (5) | 0.6426 (3) | −0.0765 (3) | 0.0503 (5) |
Source of material
A mixture of thiophene-2-carbohydrazide (142.2 mg, 1 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (170.6 mg, 1 mmol) was dissolved in 25 mL anhydrous ethanol containing a catalytic amount of glacial acetic acid. The reaction mixture was stirred under reflux for 3 h, then cooled to room temperature and filtered, and then left at room temperature. After six days, yellow block crystals were obtained.
Experimental details
All hydrogen atoms were positioned geometrically (C–H = 0.93–0.96 Å, O–H = 0.82 Å, N–H = 0.86 Å) and refined using a riding model approximation. The U iso values were constrained to be 1.5 U eq of the carrier atom for oxygen atom and methyl groups and 1.2 U eq for the remaining H atoms.
Comment
Thiophene hydrazone schiff bases are attracting more and more attention due to their biological activities and wide applications in coordination chemistry [3], [4], [5], [6], [7], [8], [9], [10].
The asymmetric unit of the title compound consists of one molecule of the organic target compound (see the figure). The title compound shows an E configuration around the C6=N2 bond. In the crystal structure, the short distance d(C6–N2) = 1.296(7) Å shows a typical C=N double bond. The angle of C6=N2–N1 is 118.4(5)°. In general the bond lengths and angles are as expected [11, 12]. The thiophene and the 5-chloro-2-hydroxyphenyl ring are almost parallel, with the dihedral angle of 1.6°. In the crystal structure, the molecules are linked into chains along the b-axis by O–H⃛N and C–H⃛O hydrogen bonds. One intramolecular N–H⃛O hydrogen bond exists, which stabilizes the conformation of the title molecule (see the figure).
Funding source: Nanyang Institute of Technology
-
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
-
Research funding: This work was financial supported by Nanyang Institute of Technology.
-
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Bruker. APEX2, SAINT and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2008.Search in Google Scholar
2. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed
3. Roymuhury, S.-K., Mandal, M., Chakraborty, D., Ramkumar, V. Homoleptic titanium and zirconium complexes exhibiting unusual Oiminol-metal coordination: application in stereoselective ring-opening polymerization of lactide. Polym. Chem. 2021, 12, 3953–3967.10.1039/D1PY00237FSearch in Google Scholar
4. Wang, P., Meng, F., Su, H., Liu, L., Khan, M.-A., Li, H. A highly selective “turn-on” water-soluble fluorescent sensor for gallium ion detection. RSC Adv. 2021, 11, 19747–19754.10.1039/D1RA02582ASearch in Google Scholar PubMed PubMed Central
5. Boulguemh, I.-E., Beghidja, A., Khattabi, L., Long, J., Beghidja, C. Monomeric and dimeric copper(II) complexes based on bidentate N′-(propan-2-ylidene) thiophene carbohydrazide Schiff base ligand: synthesis, structure, magnetic properties, antioxidant and anti-Alzheimer activities. Inorg. Chim. Acta 2020, 507, 119519.10.1016/j.ica.2020.119519Search in Google Scholar
6. Mossine, V.-V., Kelley, S.-P., Mawhinney, T.-P. Intra-molecular 1,5-S⃛N σ-hole interaction in (E)-(N)′-(pyridin-4-ylmethylidene)thiophene-2-carbohydrazide. Acta Crystallogr. 2020, E76, 557–561.10.1107/S2056989020003011Search in Google Scholar
7. Gholivand, K., Tizhoush, S.-K., Kozakiewicz, A., Eskandari, K., Farshadfar, K. Copper(I) complexes of functionalized sulfur-containing ligands: structural and theoretical insights into chalcogen bonding. CrystEngComm 2019, 21, 2675–2690.10.1039/C8CE02006JSearch in Google Scholar
8. Kundu, B.-K., Pragti, Reena, Mobin, S.-M., Mukhopadhyay, S. Mechanistic and thermodynamical aspects of pyrene based fluorescent probe to detect picric acid. New J. Chem. 2019, 43, 11483–11492.10.1039/C9NJ02342ASearch in Google Scholar
9. Ma, J.-H., Wu, W.-S., Zhang, X.-Q., Tang, S.-J., Lin, X.-Y. Bis[μ-N′-(2-oxidobenzylidene)thiophene-2-carbohydrazidato]bis[dimethanolnicke(II)]. Acta Crystallogr. 2011, E67, m910.10.1107/S160053681102143XSearch in Google Scholar
10. Ali, H., Mohammad, M., Yusof, M.-S.-M., Yamin, B.-M. Bis{μ-2′-[1-(4-chloro-2-oxidophenyl)ethylidene]thiophene-2-carbohydrazidato}bis[pyridinezinc(II)]. Acta Crystallogr. 2004, E60, m123–125.10.1107/S160053680302909XSearch in Google Scholar
11. Hussain, A., Shafiq, Z., Tahir, M. N., Yaqub, M. N′-[(E)-1-(5-chloro-2-hydroxyphenyl)ethylidene]pyridine-3-carbohydrazide monohydrate. Acta Crystallogr. 2010, E66, o1880.10.1107/S1600536810025213Search in Google Scholar PubMed PubMed Central
12. Alotaibi, M. H., Mohamed, H. A., Abdel-Wahab, B. F., Hegazy, A. S., Kariuki, Benson M., El-Hiti, G. A. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2 Z. Kristallogr. N. Cryst. Struct. 2019, 234, 355–357. https://doi.org/10.1515/ncrs-2018-0417.Search in Google Scholar
© 2022 Cui-Cui Li and Li Zhang, published by De Gruyter, Berlin/Boston
This work is licensed under the Creative Commons Attribution 4.0 International License.