Home Physical Sciences Crystal structure of 4-diethylaminobenzaldehyde isonicotinoylhydrazone monohydrate, C17H20N4O·H2O, C17H22N4O2
Article Open Access

Crystal structure of 4-diethylaminobenzaldehyde isonicotinoylhydrazone monohydrate, C17H20N4O·H2O, C17H22N4O2

  • EMAIL logo , , and
Published/Copyright: December 7, 2015
Download Article (PDF)
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 230 Issue 4

Abstract

C17H22N4O2, monoclinic, P21/c (no. 14), a = 14.382(1) Å, b = 11.3604(8) Å, c = 10.8996(7) Å, β = 105.73(1)°, V = 1714.1 Å3, Z = 4, Rgt(F) = 0.0417, wRref(F2) = 0.0819, T = 291 K.

CCDC no.:: 1267/3907

Source of material

All reagents and solvents were used as obtained commercially without further purification. A solution of 4-diethylaminobenzaldehyde (0.18 g, 1 mmol) in ethanol (15 ml) was added slowly to a solution containing isonicotinohydrazide (0.14 g, 1 mmol) in 5 ml absolute ethanol under heating and stirring. The mixture was refluxed for 1.5 h, cooled to room temperature, and the colourless solid product obtained was filtered and washed three times with ethanol. Colourless but weakly diffracting crystals of the title compound suitable for X-ray structural determination were obtained by slow evaporation of an ethanol sotution within two weeks.

Table 1

Data collection and handling.

Crystal:Colourless blocks,
size 0.36×0.40×0.40 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.82 cm−1
Diffractometer, scan mode:Gemini S Ultra, Oxford Diffraction, ω
2θmax:52.74°
N(hkl)measured, N(hkl)unique:11893, 3498
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1702
N(param)refined:218
Programs:SIR-92 [1], SHELX [6], ORTEP-3 [7]
Table 2

Atomic coordinates and displacement parameters (in Å2).

AtomSitexyzUiso
H(6)4e0.39690.27300.16120.067
H(10)4e−0.01040.48490.25740.074
H(9)4e0.12320.45600.18660.072
H(7)4e0.26320.34750.17410.065
H(13)4e0.19610.17600.41200.072
H(5)4e0.64960.30810.01830.103
H(2)4e0.5627−0.03080.17850.083
H(12)4e0.06290.20290.48400.075
H(4)4e0.54390.31860.14220.088
H(14A)4e−0.13810.31940.55610.095
H(14B)4e−0.03560.26200.58200.095
H(16A)4e−0.16510.48870.45190.091
H(16B)4e−0.10210.53320.36420.091
H(15A)4e−0.20060.19000.39370.168
H(15B)4e−0.14500.11560.51210.168
H(15C)4e−0.09760.14010.40090.168
H(17A)4e−0.18730.40990.20340.158
H(17B)4e−0.25610.50060.24300.158
H(17C)4e−0.25180.37020.29100.158
H(1)4e0.6667−0.02940.05200.097
H(2B)4e0.419(1)0.463(2)0.067(2)0.14(1)
H(2A)4e0.374(2)0.405(2)−0.036(2)0.117(9)
Table 3

Atomic coordinates and displacement parameters (in Å2).

AtomSitexyzU11U22U33U12U13U23
O(2)4e0.36975(9)0.4171(1)0.0376(1)0.0634(8)0.090(1)0.0577(8)−0.0108(7)0.0281(7)−0.0009(7)
N(2)4e0.39749(8)0.2222(1)0.2198(1)0.0463(8)0.069(1)0.0626(8)0.0078(7)0.0312(7)0.0104(7)
O(1)4e0.47275(8)0.0661(1)0.3339(1)0.0660(7)0.0819(8)0.0684(7)0.0189(7)0.0348(6)0.0193(7)
N(3)4e0.32583(9)0.2237(1)0.2832(1)0.0432(7)0.071(1)0.0603(8)0.0051(7)0.0300(7)0.0028(7)
C(10)4e0.0308(1)0.4225(2)0.2900(2)0.049(1)0.068(1)0.071(1)0.0150(9)0.0230(9)0.007(1)
N(4)4e−0.06730(9)0.3678(1)0.4302(1)0.0469(8)0.084(1)0.0734(9)0.0128(7)0.0306(8)0.0041(8)
C(9)4e0.1114(1)0.4046(1)0.2471(2)0.055(1)0.068(1)0.065(1)0.0043(9)0.0266(9)0.0089(9)
C(11)4e0.0098(1)0.3488(2)0.3816(2)0.0408(9)0.069(1)0.055(1)0.0054(9)0.0185(8)−0.0022(9)
C(6)4e0.4677(1)0.1408(2)0.2505(2)0.0429(9)0.066(1)0.055(1)0.002(1)0.0201(9)−0.0009(9)
C(8)4e0.1758(1)0.3126(1)0.2907(1)0.0409(9)0.061(1)0.054(1)0.0043(8)0.0211(8)0.0018(8)
C(7)4e0.2586(1)0.2989(2)0.2409(1)0.047(1)0.067(1)0.056(1)−0.0009(9)0.0238(9)0.0023(8)
C(13)4e0.1549(1)0.2386(2)0.3805(1)0.050(1)0.071(1)0.065(1)0.0174(9)0.0279(9)0.0120(9)
C(3)4e0.5390(1)0.1441(2)0.1725(1)0.0376(8)0.069(1)0.055(1)0.0072(9)0.0181(8)0.0034(8)
C(5)4e0.6314(1)0.2385(2)0.0502(2)0.058(1)0.105(2)0.109(2)0.006(1)0.045(1)0.028(1)
C(2)4e0.5783(1)0.0399(2)0.1459(2)0.062(1)0.082(1)0.072(1)0.016(1)0.034(1)0.011(1)
C(12)4e0.0746(1)0.2552(2)0.4243(2)0.053(1)0.075(1)0.070(1)0.016(1)0.0338(9)0.0184(9)
C(4)4e0.5673(1)0.2460(2)0.1248(2)0.053(1)0.079(1)0.102(1)0.006(1)0.043(1)0.012(1)
N(1)4e0.6686(1)0.1385(2)0.0210(2)0.062(1)0.118(2)0.088(1)0.019(1)0.0433(9)0.015(1)
C(14)4e−0.0932(1)0.2827(2)0.5155(2)0.069(1)0.094(2)0.092(1)0.014(1)0.051(1)0.006(1)
C(16)4e−0.1368(1)0.4658(2)0.3842(2)0.058(1)0.091(1)0.084(1)0.0178(9)0.029(1)−0.006(1)
C(15)4e−0.1382(2)0.1721(2)0.4496(2)0.122(2)0.092(2)0.150(2)−0.015(2)0.083(2)−0.012(2)
C(17)4e−0.2148(1)0.4338(2)0.2705(2)0.073(1)0.137(2)0.102(2)0.012(1)0.016(1)0.001(1)
C(1)4e0.6416(1)0.0420(2)0.0699(2)0.074(1)0.093(2)0.086(1)0.023(1)0.041(1)0.004(1)

Experimental details

C- and N-bound H-atoms were placed in calculated positions and treated as riding, with C–H = 0.93-97 Å, N–H = 0.86 Å, and with Uiso(H) = 1.2 Ueq(C, N) and 1.5 Ueq(C) for methyl H atoms.

Discussion

Hydrazone derivatives has attracted our much attention because they showed antibacterial and antifungal activity. [1]. As part of a general study on isonicotinoylhydrazones [2–5], the title compound has recently been prepared in our laboratory and its crystal structure is reported here. The molecular structure of the title compound is shown in the upper part of the figure. The dihedral angle between the pyridine and benzene rings is 31.2(4)°. The organic molecule present in the title structure exhibits a trans-configuration with respect to the central methylidene unit (C7=N3). The C8–C7–N3–N2 torsion angle is 178.16(14)°. In the crystal strucutre (Fig., lower part), hydrazone and water molecules are connected to a three-dimensional network by N–H⋯O, O–H⋯N and O–H⋯O hydrogen bonds.

Corresponding author: Hong Zhang, Department of Chemistry, Fuyang Normal College, Fuyang 236037, Anhui Province, P. R. China, e-mail:

Acknowledgments:

This work was supported by the Education Office of Anhui Province, People’s Republic of China (no. KJ2011A210) and Anhui Provincial Key Laboratory for Degradation & Monitoring of Pollution of the Environment (no. 2012HJJC03).

References

1. Malhotra M.; Sharma S.; Deep A. Synthesis, characterization and antimicrobial evaluation of novel derivatives of isoniazid. Med. Chem. Res. 21 (2012) 1237–1244.Search in Google Scholar

2. Souza, M. V. N. de; Wardell, S. M. S. V.; Wardell, J. L.; Low, J. N.; Glidewell, C.: 4-Cyanobenzaldehyde isonicotinoylhydrazone monohydrate: a three-dimensional hydrogen-bonded framework structure. Acta Crystallogr. C63 (2007) o166–o168.10.1107/S0108270107002788Search in Google Scholar PubMed

3. Wardell, S. M. S. V.; de Souza, M.V. N.; Ferreira, M. de L.; Vasconcelos, T. R. A.; Low, J. N.; Glidewell, C.: pi-Stacked hydrogen-bonded chains of rings in 2,4-difluorobenzaldehyde isonicotinoylhydrazone and hydrogen-bonded sheets in 2,3-dichlorobenzaldehyde isonicotinoylhydrazone. Acta Crystallogr. C61 (2005) o617–o620.10.1107/S0108270105029136Search in Google Scholar PubMed

4. Wardell, S. M. S. V.; de Souza, M. V. N.; Wardell, J. L.; Low, J. N.; Glidewell, C.: 5-Chloro-2-nitrobenzaldehyde isonicotinoylhydrazone: a three-dimensional framework built from N–H⋯N and C–H⋯O hydrogen bonds. Acta Crystallogr. E62 (2006) o3361–o3363.10.1107/S1600536806026420Search in Google Scholar

5. Xia, L.-Y.; Wang, W.-L.; Wang, S.-H.; Huang, Y.-L.; Shan, S.: N′-[(E)-3-Indol-3-ylmethylene]isonicotinohydrazide monohydrate. Acta Crystallogr. E65 (2009) o1900.10.1107/S1600536809027329Search in Google Scholar PubMed PubMed Central

6. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

7. Farrugia, L. J.: ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI). J. Appl. Crystallogr. 30 (1997) 565.Search in Google Scholar

Received: 2012-9-11
Accepted: 2012-11-21
Published Online: 2015-12-7
Published in Print: 2015-12-1

©2015 Hong Zhang et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidozincate(II), C40H40Br4P2Zn
  3. Crystal structure of chlorido-(2-ethoxy-6-(((quinolin-8-yl)methyl)-phenolato-κ3N,N′,O)-copper(II), C18H15ClCuN2O2
  4. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidocobaltate(II), C40H40Br4CoP2
  5. Crystal structure of di(pyrrolidin-1-yl)methane-thione, C9H16N2S
  6. Crystal structure of ammonium phenylglyoxylate, C8H9NO3
  7. Crystal structure of 2-hydroxy-2-methyl-2-phenyl acetic acid hemihydrate, C9H11O3.50
  8. Crystal structure of 2-((E)-2-(1H-benzo[d]imidazol-2-yl)vinyl)-1H-benzo[d]imidazolium dichloride dihydrate, C16H18Cl2N4O2
  9. Crystal structure of 1,2-dimethylimidazolium iodide, C5H9IN2
  10. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraqua-cobalt(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34CoN2O14
  11. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-bis(thiophene-3,4-dicarboxylato-κ2O,O′)-cadmium(II), C32H22CdN4O8S2
  12. Crystal structure of tetraaqua-(4,4′-diamino-1,1′-biphenyl-2,2′-disulfonato-κN)(4,4′-bipyridyl-κN)zinc(II) trihydrate, C22H32N4O13S2Zn
  13. Crystal structure of poly[[[(1,3-dimethyl-2-imidazolidinone-κ1O11) zinc(II)]-μ-1,4-benzenedi-carboxylato-κ4O1,O2:O3,O4]—1,3-dimethyl-2-imidazolidinone (1:1)], [Zn(C5H10N2O)(C8H4O4)]· C5H10N2O, C18H24N4O6Zn
  14. Crystal structure of poly[[(1,3-dimethyl-2-imidazolidinone-κ1O) zinc(II)]-μ-furan-2,5-dicarboxylato-κ4O,O′:O′′,O′′′], [Zn(C5H10N2O)(C6H2O5)], C22H24N4O12Zn2
  15. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraquamanganese(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34MnN2O14
  16. Crystal structure of chlorido-tricarbonyl-bis(2-pyridylmethanone-N,N′)-rhenium(I), C14H8ClN2O4Re
  17. Crystal structure of (2-(benzoyl)phenolato-κ2O,O′)-trans-dichlorido -cis- bis(methoxido) niobium(V), C15H15Cl2NbO4
  18. Crystal structure of potassium diaqua dihydroxy(methylenediphosphonato-κ2-O,O′)cobaltate(III), CH10CoKO10P2
  19. Crystal structure of hexakis(4-(dimethylamino)pyridin-1-ium) decavanadate-water (1:16), C42H98N12O44V10
  20. Crystal structure of 4-diethylaminobenzaldehyde isonicotinoylhydrazone monohydrate, C17H20N4O·H2O, C17H22N4O2
  21. Crystal structure of bis[μ-1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κ2N:N′]bis[dibromido]dimercury(II), C24H26Br4Hg2N10
  22. Crystal structure of poly{bis-[(4,4′-biphenyl-dicarboxylate-κ2O:O′)-μ-1,1′-oxy-bis-(ethane-2,1-diyl)-bis-(1H-imidazole)-κ2N:N′] zinc(II)}dihydrate, C48H48N8O12Zn2
  23. Crystal structure of sodium poly[(μ4-2,2′,2′′-nitrilotriacetato-κ4O,O′,O′′,N)magnesium(II)] monohydrate
  24. The crystal structure of 1-(2-(2-chloroethoxy)phenyl)ethanone
  25. The crystal structure of tris(μ2-1,3-bis(4,4,4-Trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-/κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-O,O′)-diterbium(III)
  26. Crystal structure of (S)-2-(2,2′-diethoxy-[1,1′-binaphthalen]-6-yl)-4,4,5,5-tetra-methyl-2-imidazoline-1-oxyle, C31H33N2O3
  27. Crystal structure of cis-tetrachloridobis-(pyridine-κN)platinum(IV), C10H10Cl4N2Pt
  28. Crystal structure of catena-poly[aqua-(μ2-5-norbornene-2,3-dicarboxylato-κ3O,O′:O′′)-(1,10-phenanthroline-κ2N,N′)zinc(II)], [Zn(C9H8O4)(C12H8N2)(H2O)]n
https://doi.org/10.1515/ncrs-2013-0042
Creative Commons
BY-NC-ND 3.0

Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidozincate(II), C40H40Br4P2Zn
  3. Crystal structure of chlorido-(2-ethoxy-6-(((quinolin-8-yl)methyl)-phenolato-κ3N,N′,O)-copper(II), C18H15ClCuN2O2
  4. Crystal structure of bis(ethyltriphenylphos-phonium) tetrabromidocobaltate(II), C40H40Br4CoP2
  5. Crystal structure of di(pyrrolidin-1-yl)methane-thione, C9H16N2S
  6. Crystal structure of ammonium phenylglyoxylate, C8H9NO3
  7. Crystal structure of 2-hydroxy-2-methyl-2-phenyl acetic acid hemihydrate, C9H11O3.50
  8. Crystal structure of 2-((E)-2-(1H-benzo[d]imidazol-2-yl)vinyl)-1H-benzo[d]imidazolium dichloride dihydrate, C16H18Cl2N4O2
  9. Crystal structure of 1,2-dimethylimidazolium iodide, C5H9IN2
  10. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraqua-cobalt(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34CoN2O14
  11. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-bis(thiophene-3,4-dicarboxylato-κ2O,O′)-cadmium(II), C32H22CdN4O8S2
  12. Crystal structure of tetraaqua-(4,4′-diamino-1,1′-biphenyl-2,2′-disulfonato-κN)(4,4′-bipyridyl-κN)zinc(II) trihydrate, C22H32N4O13S2Zn
  13. Crystal structure of poly[[[(1,3-dimethyl-2-imidazolidinone-κ1O11) zinc(II)]-μ-1,4-benzenedi-carboxylato-κ4O1,O2:O3,O4]—1,3-dimethyl-2-imidazolidinone (1:1)], [Zn(C5H10N2O)(C8H4O4)]· C5H10N2O, C18H24N4O6Zn
  14. Crystal structure of poly[[(1,3-dimethyl-2-imidazolidinone-κ1O) zinc(II)]-μ-furan-2,5-dicarboxylato-κ4O,O′:O′′,O′′′], [Zn(C5H10N2O)(C6H2O5)], C22H24N4O12Zn2
  15. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)-tetraquamanganese(II)] – (3-(carboxylatomethyl)benzoic acid) – water (1/2/2), C28H34MnN2O14
  16. Crystal structure of chlorido-tricarbonyl-bis(2-pyridylmethanone-N,N′)-rhenium(I), C14H8ClN2O4Re
  17. Crystal structure of (2-(benzoyl)phenolato-κ2O,O′)-trans-dichlorido -cis- bis(methoxido) niobium(V), C15H15Cl2NbO4
  18. Crystal structure of potassium diaqua dihydroxy(methylenediphosphonato-κ2-O,O′)cobaltate(III), CH10CoKO10P2
  19. Crystal structure of hexakis(4-(dimethylamino)pyridin-1-ium) decavanadate-water (1:16), C42H98N12O44V10
  20. Crystal structure of 4-diethylaminobenzaldehyde isonicotinoylhydrazone monohydrate, C17H20N4O·H2O, C17H22N4O2
  21. Crystal structure of bis[μ-1-[(2-ethyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κ2N:N′]bis[dibromido]dimercury(II), C24H26Br4Hg2N10
  22. Crystal structure of poly{bis-[(4,4′-biphenyl-dicarboxylate-κ2O:O′)-μ-1,1′-oxy-bis-(ethane-2,1-diyl)-bis-(1H-imidazole)-κ2N:N′] zinc(II)}dihydrate, C48H48N8O12Zn2
  23. Crystal structure of sodium poly[(μ4-2,2′,2′′-nitrilotriacetato-κ4O,O′,O′′,N)magnesium(II)] monohydrate
  24. The crystal structure of 1-(2-(2-chloroethoxy)phenyl)ethanone
  25. The crystal structure of tris(μ2-1,3-bis(4,4,4-Trifluoro-3-oxido-1-(oxo)but-2-en-1-yl)phenyl-/κ4O,O′:O′′,O′′′)-bis(1,2-dimethoxyethane-O,O′)-diterbium(III)
  26. Crystal structure of (S)-2-(2,2′-diethoxy-[1,1′-binaphthalen]-6-yl)-4,4,5,5-tetra-methyl-2-imidazoline-1-oxyle, C31H33N2O3
  27. Crystal structure of cis-tetrachloridobis-(pyridine-κN)platinum(IV), C10H10Cl4N2Pt
  28. Crystal structure of catena-poly[aqua-(μ2-5-norbornene-2,3-dicarboxylato-κ3O,O′:O′′)-(1,10-phenanthroline-κ2N,N′)zinc(II)], [Zn(C9H8O4)(C12H8N2)(H2O)]n
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Winner of the OpenAthens UX Award 2026
Winner of the OpenAthens UX Award 2026
Have an idea on how to improve our website?
Please write us.
© 2026 De Gruyter Brill
Downloaded on 27.3.2026 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2013-0042/html
Scroll to top button