Startseite The crystal structure of (E)-2-(2-((2-picolinoylhydrazono)methyl)phenoxy)acetic acid dihydrate, C15H17N3O6
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The crystal structure of (E)-2-(2-((2-picolinoylhydrazono)methyl)phenoxy)acetic acid dihydrate, C15H17N3O6

  • Tai Xi-Shi ORCID logo , Ren Zhen , Liu Li-Li , Zhang Ai-Ling EMAIL logo und Wang Li-Hua
Veröffentlicht/Copyright: 3. Dezember 2020

Abstract

C15H17N3O6, triclinic, P1 (no. 2), a = 7.2155(8) Å, b = 10.7519(8) Å, c = 10.8562(8) Å, α = 107.910(7), β = 97.087(8), γ = 100.409(7) V = 773.69(12) Å3, Z = 2, Rgt(F) = 0.0500, wRref(F2) = 0.1238, T = 150(1) K.

CCDC no.: 2043966

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:Colourless block
Size:0.12 × 0.10 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.11 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:5320, 2732, 0.042
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1836
N(param)refined:224
Programs:Bruker [1], Olex2 [2], SHELX [3], Diamond [4]
Table 2:

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

AtomxyzUiso*/Ueq
O10.6069 (3)0.83791 (15)0.51295 (15)0.0343 (5)
O20.8323 (2)0.24274 (14)0.43498 (14)0.0276 (4)
O30.8027 (3)0.11628 (15)0.18016 (15)0.0361 (5)
O40.9119 (3)−0.05242 (15)0.21748 (15)0.0328 (5)
H40.895523−0.0820090.1367620.049*
N10.5153 (3)0.65522 (18)0.17074 (18)0.0302 (5)
N20.6282 (3)0.62735 (17)0.39873 (17)0.0235 (5)
H20.6065170.5657280.3226610.028*
N30.7051 (3)0.60268 (18)0.50855 (17)0.0231 (5)
C10.5115 (3)0.7574 (2)0.2787 (2)0.0249 (6)
C20.4448 (4)0.8691 (2)0.2737 (2)0.0296 (6)
H2A0.4447820.9379790.3506670.036*
C30.3783 (4)0.8755 (2)0.1516 (3)0.0345 (7)
H30.3315820.9486890.1446310.041*
C40.3822 (4)0.7720 (3)0.0404 (3)0.0379 (7)
H4A0.3390040.774163−0.0431000.046*
C50.4511 (4)0.6653 (3)0.0550 (2)0.0371 (7)
H50.4528590.595767−0.0208400.044*
C60.5864 (3)0.7461 (2)0.4083 (2)0.0246 (6)
C70.7509 (3)0.4901 (2)0.4857 (2)0.0226 (6)
H70.7293950.4320380.3991530.027*
C80.8361 (3)0.4496 (2)0.5918 (2)0.0221 (5)
C90.8820 (4)0.5367 (2)0.7218 (2)0.0281 (6)
H90.8557930.6214960.7413770.034*
C100.9652 (4)0.4996 (2)0.8219 (2)0.0318 (6)
H100.9956370.5590810.9081660.038*
C111.0035 (4)0.3734 (2)0.7935 (2)0.0294 (6)
H111.0596750.3480530.8610000.035*
C120.9590 (4)0.2849 (2)0.6659 (2)0.0262 (6)
H120.9842940.1999230.6475990.031*
C130.8768 (3)0.3223 (2)0.5652 (2)0.0215 (5)
C140.8914 (4)0.1193 (2)0.4014 (2)0.0267 (6)
H14A0.8162430.0571630.4349230.032*
H14B1.0256640.1345070.4397760.032*
C150.8618 (4)0.0624 (2)0.2544 (2)0.0247 (6)
O50.8818 (3)−0.1644 (2)−0.03305 (16)0.0407 (5)
H5A0.979458−0.145209−0.0659530.061*
H5B0.780487−0.180286−0.0896710.061*
O60.5732 (3)−0.2216 (2)−0.23826 (17)0.0445 (5)
H6A0.472136−0.191659−0.2334320.067*
H6B0.607254−0.223954−0.3109320.067*

Source of material

The title compound has been synthesized according to the following method: a mixture of 0.0895 g 2-formyl phenoxyacetic acid (0.5 mmol), 0.0685 g pyridine-2-carbohydrazide (0.5 mmol) and 0.020 g sodium hydroxide (0.5 mmol) were stirred and dissolved in 10 mL ethanol-water (v:v = 1:1). After complete dissolution, 0.0595 g calcium perchlorate hydrate (0.25 mmol) was added to the above solution. The reaction mixture was stirred for 3 h at 70 °C, cooled to room temperature and filtered. The colorless crystals of the title compound were obtained from the solution after 25 days.

Experimental details

The hydrogen atoms were positioned geometrically (C-H = 0.93–0.97 Å, N-H = 0.86 Å and O-H = 0.82–0.85 Å). Their Uiso values were set to 1.2Ueq or 1.5Ueq of the parent atoms.

Comment

Hydrazones and their metal complexes have found considerable applications in catalysis [5], and some show anticancer and antimicrobial activities [6], [7], or are used as electrochemical sensors [8]. Our research group has been devoted to the study of hydrazones [9], [10], [11].

The title compound consists of one (E)-2-(2-((2-picolinoylhydrazono)methyl)phenoxy)acetic acid molecule and two lattic water molecules (the Figure). The bond distance of C7-N3 is 1.272(2) Å, which is shortest among those of C6-N2 (1.341(2) Å), C1-N1 (1.344(3) Å) and C5-N1 (1.328(3) Å), showing that the C7-N3 bond is a double bond [12], [13]. The bond distances of C6-O1 (1.226(3) Å) and C15-O3 (1.208(2) Å) are shorter than that of C15-O4 (1.307(2) Å), showing that the C6-O1 and C15-O3 bonds are also double bonds. The dihedral angle between the benzene ring (C8-C9-C10-C11-C12-C13) and pyridine ring (C1-C2-C3-C4-C5-N1) is 8.0°, indicating that the whole hydrazone molecule is almost coplanar. In the crystal packing, the chain structure was formed by intermolecular O-H⋯O hydrogen bonds.


Corresponding author: Zhang Ai-Ling, College of Chemistry and Chemical Engineering, Weifang University, Weifang, Shandong, 261061, P.R. China, E-mail:

Award Identifier / Grant number: 21171132

Award Identifier / Grant number: ZR2014BL003

Funding source: the project of Shandong Province Higher Educational Science and Technology Program

Award Identifier / Grant number: J14LC01

Funding source: Science Foundation of Weifang

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

  2. Research funding: 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.

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

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Received: 2020-10-12
Accepted: 2020-11-12
Published Online: 2020-12-03
Published in Print: 2021-03-26

© 2020 Tai Xi-Shi et al., 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. The crystal structure of 4-hydroxybenzene-1,3-diaminium dichloride, C6H10Cl2N2O
  4. The crystal structure of 3-chloropropylammonium chloride, C3H9Cl2N
  5. The crystal structure of 1-chloro-2-(dimethylamino)ethane hydrochloride, C4H11Cl2N
  6. Crystal structure of N-(2-(trifluoromethyl)phenyl)hexanamide, C13H16F3NO
  7. Redetermination of the crystal structure of para-toluidine, C7H9
  8. The crystal structure of bis(1,3-dihydroxy-2-methylpropan-2-aminium) carbonate, C9H24N2O7
  9. The crystal structure of 4-chloro-1-methylpiperidin-1-ium chloride, C6H13Cl2N
  10. Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
  11. The crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H21F2NO4
  12. Crystal structure of 6,6'‐((1E,1'E)‐(propane‐1,3‐diylbis(azaneylylidene))bis(methaneylylidene))bis(3‐bromophenol), C34H32Br4N4O4
  13. The crystal structure of (E)-2-(2-((2-picolinoylhydrazono)methyl)phenoxy)acetic acid dihydrate, C15H17N3O6
  14. Crystal structure of (E)-4-bromo-N′-(3-chloro-2-hydroxybenzylidene)benzohydrazide, C14H10BrClN2O2
  15. Crystal structure of N,N′-bis(4-bromosalicylidene) ethylene-1,2-diaminopropan, C34H32Br4N4O4
  16. Crystal structure of 4-bromo-N′-[(3-bromo-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H14Br2N2O3
  17. The crystal structure of 1,2-bis(1H-benzo[d]imidazol-2-yl)ethane-1,2-diol — N-(2-aminophenyl)-3-(1H-benzo[d]imidazol-2-yl)-2,3-dihydroxypropanamide (1/1), C32H30N8O5
  18. The crystal structure of para-trifluoromethyl-aniline hemihydrate, C14H14F6N2O
  19. Redetermination of the crystal structure of 2-amino-2-methyl-propane-1,3-diole, C4H11NO2
  20. The crystal structure of methacholine chloride, C8H18ClNO2
  21. Crystal structure of 5,7,7-trimethyl-4,6,7,8-tetrahydrocyclopenta[g]isochromen-1(3H)-one, C15H18O2
  22. Crystal structure of poly[diammine-bis(μ4-4-hydroxypyridine-3-sulfonato-κ5N:O, O′:O′′:O′′)(μ2-pyrazinyl-κ2N:N′)tetrasilver(I)], C7H8Ag2N3O4S
  23. Crystal structure of ethyl (E)-5-(((3′,6′-bis(ethylamino)-3-oxospiro[isoindoline-1,9′-xanthen]-2-yl)imino)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate — ethanol (1/1), C38H45N5O5
  24. Crystal structure of 4-bromo-N′-[(3-chloro-2-hydroxyphenyl)methylidene]benzohydrazide, C14H7Br2N2O2
  25. Redetermination of the crystal structure of 3,3,3-triphenylpropanoic acid, C21H18O2 – Deposition of hydrogen atomic coordinates
  26. Structure redetermination of dextromethorphan hydrobromide monohydrate, C18H28BrNO2 – localization of hydrogen atoms
  27. Crystal structure of tris(azido-κ1N)-(N-(2-aminoethyl)-N-methyl-1,3-propanediamine-κ3N,N′,N′′)cobalt(III), C7H19CoN12
  28. Crystal structure of tetraaqua-bis(1H-indazole-6-carboxylate-κN)cadmium (II), C16H18CdN4O8
  29. Crystal structure of dichloride-bis(1-propylimidazole-κ1N)zinc(II), C12H20Cl2N4Zn
  30. Crystal structure of (E)-resveratrol 3-O-β-D-xylopyranoside, C19H22O8
  31. Crystal structure of 3,3′-(1,2-phenylene-bis(methylene))bis(1-vinyl- 1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C18H20F12N4P2
  32. Crystal structure of diaqua[bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″]-phthalato-κ1O-nickel(II)-methanol (1/2), C26H31N5NiO8
  33. Crystal structure of 6,7-difluoro-1-methyl-3-(trifluoromethyl)quinoxalin-2(1H)-one, C10H5F5N2O
  34. Crystal structure of dichlorido-bis(1-hexyl-1H-benzotriazole-k1N)zinc(II), C24H34N6Cl2Zn
  35. The crystal structre of 2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, C16H12BBrN2
  36. Crystal structure of diethyl 3,9-bis(4-fluorophenyl)-6,12-diphenyl-3,9-diazapentacyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C40H36F2N2O4
  37. Crystal structure of (E)-7-methoxy-2-((5-methoxypyridin-3-yl)methylene)-3,4- dihydronaphthalen-1(2H)-one, C18H17NO3
  38. Crystal structure of (E)-2-chloro-6-(((1,3-dihydroxy-2-(oxidomethyl)propan-2-yl)imino)methyl)phenolate-κ3N,O,O’)manganese(IV), C22H24Cl2MnN2O8
  39. The crystal structure of α-(meta-methoxyphenoxy)-ortho-tolylic acid, C15H14O4
  40. The crystal structure of N-(2-chloroethyl)-N,N-diethylammonium chloride, C6H15Cl2N
  41. The crystal structure of tris(2,3,4,6,7,8,9,10-octahydro-1H-pyrimido[1,2-a]azepin-5-ium) trihydrodecavanadate(V), C27H54N6O28V10
  42. Crystal structure of 1,3-bis(octyl)benzimidazolium perchlorate C23H39ClN2O4
  43. Crystal structure of tetrakis[(Z)-(2-(1-(furan-2-yl)-2-methylpropylidene)-1-phenylhydrazin-1-ido-κ2N,N′)] zirconium(IV), C56H60N8O4Zr
  44. The crystal structure of 2-(naphthalen-2-yloxy)-4-phenyl-6-(prop-2-yn-1-yloxy)-1,3,5-triazine, C22H15N3O2
  45. The crystal structure of trimethylsulfonium tris(trifluoromethylsulfonyl)methanide, C7H9F9O6S4
  46. Crystal structure of 4-bromo-N′-[3,5-dichloro-2-hydroxyphenyl)methylidene]benzohydrazide methanol solvate, C15H13BrCl2N2O3
  47. The crystal structure of 4-(4-bromophenyl)-2-(3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazole, C24H16Br2FN3S
  48. The crystal structure of N-(adamantan-1-yl)-piperidine-1-carbothioamide, C16H26N2S
  49. The crystal structure of 1-phenyl-N-(4,5,6,7-tetrabromo-1,3-dioxoisoindolin-2-yl)-5-(thiophen-2-yl)-1H-pyrazole-3-carboxamide-dimethylformamide (1/1) C22H10Br4N4O3S
  50. The crystal structure of benzeneseleninic acid anhydride, C12H10O3Se2
  51. The crystal structure of diphenyalmine hydrochloride antimony trichloride co-crystallizate, C12H12Cl4NSb – Localization of hydrogen atoms
  52. The crystal structure of para-nitrobenzylbromide, C7H6BrNO2 – A second polymorph and correction of 3D coordinates
  53. Crystal structure of catena-poly[(5H-pyrrolo[3,2-b:4,5-b′]dipyridine-κ2N,N′)-(μ4-hexaoxidodivanadato)dizinc(II)],C10H9N3O6V2Zn
  54. Crystal structure of N,N′-(2-hydroxypropane-1,3-diyl)bis(pyridine-2-aldimine)-κ5N,N′,N′′,N′′′,O]-tris(nitrato-κ2O,O′) cerium(III), C15H16CeN7O10
  55. Synthesis and crystal structure of oktakis(dimethylsulphoxide-κ1O)gadolinium(III) [tetrabromido-μ2-bromido-μ2-sulfido-di-μ3-sulfido-μ4-sulfido-tetracopper(I)-tungsten(VI)], C16H48O8S12Br5Cu4GdW
  56. Crystal structure of {tris((1H-benzo[d]imidazol-2- yl)methyl)amine-κ4N,N′,N′′,N′′′}-(succinato-κ2O,O′)nickel(II) – methanol (1/4), C32H41N7NiO8
  57. Crystal structure of catena-poly[trans-tetraaqua(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-k2N:N′)cobalt(II)] dinitrate – 1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol) – water (1/3/2), C72H68CoN18O12
  58. Crystal structure of bis(μ2-2-oxido-2-phenylacetate-κ3O:O,O′)-bis(1-isopropoxy-2-oxo-2-phenylethan-1-olato-κ2O,O′)-bis(propan-2-olato-κ1O)dititanium(IV), C44H52O14Ti2
  59. The crystal structure of 5-carboxy-2-(hydroxymethyl)-1H-imidazol-3-ium-4-carboxylate, C6H8N2O6
  60. The crystal structure of 2,6-dibromo-4-fluoroaniline, C6H4Br2FN
  61. The crystal structure of 4-chloro-N-(2-phenoxyphenyl)benzamide, C19H14ClNO2
  62. The crystal structure of 2-methyl-β-naphthothiazole, C12H9NS
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