Startseite Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
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Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S

  • Cui-Cui Li und Li Zhang ORCID logo EMAIL logo
Veröffentlicht/Copyright: 26. Januar 2022

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.

CCDC no.: 2141830

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.

Table 1:

Data collection and handling.

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]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

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).


Corresponding author: Li Zhang, Changchun Oubang Biotechnology Co., Ltd., 130000, Changchun, Jilin, People’s Republic of China, E-mail:

Funding source: Nanyang Institute of Technology

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was financial supported by Nanyang Institute of Technology.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2021-12-01
Accepted: 2022-01-13
Published Online: 2022-01-26
Published in Print: 2022-04-26

© 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.

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
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  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
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  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
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  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
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