Startseite The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-3-yl-methylene)aniline, C18H22N2
Artikel Open Access

The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-3-yl-methylene)aniline, C18H22N2

  • Eric M. Njogu , Bernard Omondi EMAIL logo und Vincent O. Nyamori
Veröffentlicht/Copyright: 4. Mai 2017

Abstract

C18H22N2, monoclinic, P21/c (no. 14), a = 8.1226(5) Å, b = 17.4745(10) Å, c = 11.1822(6) Å, β = 102.549(2)°, V = 1549.27(15) Å3, Z = 4, Rgt(F) = 0.0397, wRref(F2) = 0.1071, T = 100 K.

CCDC no.:: 1542738

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow block
Size:0.43 × 0.26 × 0.17 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.7 cm−1
Diffractometer, scan mode:Bruker APEX-II, 0.5° φ and ω
2θmax, completeness:57.4°, >98%
N(hkl)measured, N(hkl)unique, Rint:33181, 3931, 0.021
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3545
N(param)refined:185
Programs:Bruker programs [1], SHELX [2], WinGX/ORTEP [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.34833(11)0.64738(5)0.60096(8)0.01602(18)
C20.30049(12)0.70939(5)0.66375(8)0.02001(19)
H70.3120.75820.63350.024*
C30.22312(12)0.63202(6)0.80589(8)0.0226(2)
H80.17830.62620.87520.027*
C40.26954(12)0.56649(6)0.75127(9)0.0233(2)
H180.25780.51840.78410.028*
C50.33381(12)0.57414(5)0.64678(8)0.01968(19)
H170.36650.53140.60820.024*
C60.40666(11)0.66000(5)0.48681(8)0.01602(17)
H50.3970.70840.45130.019*
C70.51963(11)0.61975(5)0.32373(8)0.01533(17)
C80.42508(11)0.58385(5)0.21851(8)0.01740(18)
C90.47598(13)0.59384(6)0.10820(8)0.0217(2)
H130.41560.57040.03750.026*
C100.61551(13)0.63829(6)0.10263(9)0.0237(2)
H120.6460.64580.0280.028*
C110.70987(12)0.67166(5)0.20807(9)0.0216(2)
H110.80410.70080.20330.026*
C120.66605(11)0.66234(5)0.32122(8)0.01709(18)
C130.77693(12)0.69177(5)0.43978(9)0.02083(19)
H140.70250.71390.48890.025*
C140.87142(14)0.62468(7)0.51277(10)0.0303(2)
H16A0.79150.5880.52970.045*
H16B0.93880.64330.58850.045*
H16C0.9430.60080.46580.045*
C150.90104(14)0.75386(6)0.42126(11)0.0292(2)
H15A0.98380.73230.38150.044*
H15B0.95610.77440.49940.044*
H15C0.84130.7940.37120.044*
C160.26958(12)0.53817(5)0.22785(9)0.02170(19)
H20.28740.51850.31170.026*
C170.23722(15)0.46955(7)0.14145(12)0.0340(3)
H9A0.21020.48720.05820.051*
H9B0.14470.44020.15780.051*
H9C0.33640.43810.1540.051*
C180.11433(13)0.59002(7)0.20711(12)0.0316(2)
H1A0.1370.63340.26080.047*
H1B0.02030.5620.2240.047*
H1C0.08820.60720.12360.047*
N10.23878(11)0.70302(5)0.76510(8)0.02318(18)
N20.47006(9)0.60572(4)0.43607(7)0.01613(16)

Experimental details

Crystal evaluation and data collection were done on a Bruker Smart APEX2 diffractometer [1] with Mo Kα radiation (λ = 0.71073 Å) operating at 100(1) K. The structure was solved by the direct method using the SHELXS [2] program and refined. The structure was visualised using the ORTEP-3 [3] system software. All non-hydrogen atoms were refined anisotropically with full-matrix least squares method based on F2 using SHELXL [2]. All hydrogen atoms were placed in idealized positions and refined as riding on their parent atoms. The basic structural motif is a centrosymmetric dimer. Such dimers stack in a zig zag fashion forming columns that run along the crystallographic b axis. Several C–H⋯π interactions contribute to the stability of the 3D structure.

Comment

The molecular structure of the title compound bears a phenylimine moiety and 2,6-diisopropyl aniline linked (together) by an azomethine unit. The planes of the aromatic part of the aniline moiety and the pyridin-3-yl-methylene moiety show a dihedral angle of 60°. The aryl moieties are in E-configuration (cf. the figure). The C6—N2 imine bond length of 1.2704(11) Å, is perfectly within the expected range and is close to those of similar compounds reported in literature [4], [5], [6], [7].

Acknowledgement

We acknowledge the National Research Foundation and University of KwaZulu-Natal, South Africa for financial support for Eric N Njogu.

References

1 Bruker.: APEX2, SAINT and SADABS. Brucker AXS Inc., Madison, Wisconsin, USA (2009).Suche in Google Scholar

2 Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Suche in Google Scholar PubMed

3 Farrugia, L. J.: WinGX and ORTEP for Windows. Appl. Crystallogr. 45 (2012) 849–854.10.1107/S0021889812029111Suche in Google Scholar

4 Cuffini, S.; Glidewell, C.; Low, J. N.; de Oliveira, A. G.; de Souza, M. V. N.; Vasconcelos, T. R. A.; Wardell, S. M. S. V.; Wardell, J. L.: Nine N-aryl-2-chloronicotinamides: supramolecular structures in one, two and three dimensions. Acta Crystallogr. B62 (2006) 651–665.10.1107/S0108768106015497Suche in Google Scholar PubMed

5 Ha, K.: A centrosymmetric monoclinic polymorph of N1,N4-bis(pyridin-3-ylmethylidene)benzene-1,4-diamine. Acta Crystallogr. E67 (2011) o2250.10.1107/S1600536811030789Suche in Google Scholar PubMed PubMed Central

6 Paul, M.; Dastidar, P.: Coordination polymers derived from pyridyl carboxylate ligands having an amide backbone: an attempt towards the selective separation of CuII cation following in situ crystallization under competitive conditions. CrystEngComm 16 (2014) 7815–7829.10.1039/C4CE00733FSuche in Google Scholar

7 Bacchi, A.; Carcelli, M.; Chiodo, T.; Mezzadri, F.; Nestola, F.; Rossi, A.: Inclusion properties, polymorphism and desolvation kinetics in a new 2-pyridyl iminophenol compound with 1D nanochannels. Cryst. Growth Des. 9 (2009) 3749–3758.10.1021/cg900442xSuche in Google Scholar

Received: 2016-11-18
Accepted: 2017-4-6
Published Online: 2017-5-4
Published in Print: 2017-7-26

©2017 Eric M. Njogu et al., published by De Gruyter.

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

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)manganese(II)] bis(4-chlorobenzenesulfonate) – 4,4′-bipyridine – water (1/1/2) C42H40Cl2MnN6O10S2
  3. The crystal structure of 1,2-bis[2-methyl-5-(3-cyanophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H16F6N2S2
  4. Crystal structure of the first characterized polymeric copper and sodium complex diaqua-(tris-acetato-κO,O′)(μ2-acetato-κO′′)dinatrium copper(II) monohydrate, C8H18CuNa2O11
  5. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-3-yl-methylene)aniline, C18H22N2
  6. Crystal structure of methyl 2,7,7-trimethyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C20H22N2O5
  7. Crystal structure of bis(1,3-bis(diphenylphosphino)propane-κ2P,P′)silver(I) trifluorosulfonate–methanol (1:0.5), [Ag(C27H26P2)]SO3CF3⋅0.5CH3OH
  8. Crystal structure of μ-1,4-bis(diphenylphosphine)butane-2,9-dimethyl-1,10-phenanthroline-κ2N:N′-bis(cyano-κC)dicopper(I)]-water, C58H56Cu2N6O2P2
  9. Crystal structure of N2,N6-bis(1-hydrazinyl-2-methyl-1-oxopropan-2-yl) pyridine-2,6-dicarboxamide, C15H23N7O4
  10. Crystal structure of 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide, C19H17IN2
  11. Crystal structure of diaqua-(2,2′-(butane-1,4-diyl)-bis(5-carboxy-1H-imidazole-4-carboxylato)-κ4O,O′,N,N′)cadmium(II) monohydrate, C14H18O11N4Cd
  12. Crystal structure of ethyl (E)-3-(cyclopropylamino)-2-(2,4-dichloro-5-fluorobenzoyl) acrylate, C15H14Cl2FNO3
  13. Crystal structure of bis-(1-(4-chlorophenyl)-3-phenyl-4-thenoyl-1H-pyrazol-5-ol-κ2O,O′)-(N,N-dimethylformamide)zinc(II), C43H31Cl2N5O5S2Zn
  14. Crystal structure of tetrakis(μ3-2-(N-(2-hydroxyethyl)amino)ethoxo)-tetrachloro-tetra-cobalt(II) methanol solvate, C17H44Cl4Co4N4O9
  15. Crystal structure of 3-amino-1-(4-bromophenyl)-9-methoxy-1H-benzo[f]chromene-2-carbonitrile, C21H15BrN2O2
  16. Crystal structure of 2-amino-4-(4-isopropyl-phenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene, C22H18N2O3
  17. Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C22H18N2O3
  18. Crystal structure of monoaqua-[6,6′-((1E,1′E)-(1,2-phenylene bis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-nitrophenolato-κ4N,N′,O,O′)]zinc(II), C20H12Br2N4O7Zn
  19. Crystal structure of 11-(4-(dimethylamino)phenyl)-17-hydroxy-13-methyl-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one – acetonitril (1/2), C33H41N3O2
  20. Crystal structure of tert-butyl (phenylsulfinyl)carbamate, C11H15NO3S
  21. Crystal structure of catena-poly{diaqua-bis(3-(1H-1,2,4-triazol-1-yl)benzoato-κ2O:N)copper(II)} monohydrate, C18H18CuN6O7
  22. Crystal structure of tetraaqua-bis(3-(4H-1,2,4-triazol-4-yl)benzoato-κN)cobalt(II), C18H20CoN6O8
  23. The crystal structure of 4-bromo-N-cyclopropyl-2,5-difluorobenzenesulfonamide, C9H8BrF2NO2S
  24. Crystal structure of ([3,3′-bipyridine]-6,6′-dicarboxylato-κ2O:O′)-bis(1,2-bis(4-pyridyl)ethane-κ2N:N′)disilver(I) dihydrate, C37H35Ag2N5O6
  25. The crystal structure of (4-(1H-1,2,4-triazol-1-yl)benzoato-κN)-[4-(1H-1,2,4-triazol-1-yl)benzoic acid-κN]silver(I), C18H13AgN6O4
  26. Crystal structure of 3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one, C17H16O2
  27. Crystal structure of bis(2-((E)-((4-((E)-1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-methoxyphenolato-κ2O,N)copper(II), C36H38CuN4O6
  28. Crystal structure of poly[1,2-bis(1,2,4-triazol-4-yl)ethane-κ2N:N′]silver(I) bromate monohydrate]silver(I), C6H10AgBrN6O4
  29. The crystal structure of 2,3,5-triphenyl-2,3-dihydro-1H-tetrazol-1-ium 2,3-dioxoindoline-5-sulfonate, C27H19N5O5S
  30. Crystal structure of 3-(2-amino-1,3-selenazol-4-yl)-2H-chromen-2-one – dimethylformamide (1/1), C15H15N3O3Se
  31. Crystal structure of diethyl 3,3′-(diazene-1,2-diyl)(E)-dibenzoate, C18H18N2O4
  32. Crystal structure of cis-bis((1H-benzimidazol-2-yl)methanol-κN,O)-bis(isothiocyanato-κN)nickel(II), C18H16N6NiO2S2
  33. Crystal structure of bis(2-(2′-hydroxy-5′-methoxyphenyl)-1H-benzimidazole)boron – tetrahydrofuran (1/1), C36H37N4O6B
  34. Crystal structure of poly[aqua-bis(nitrato-κ2O,O′)-(μ3-1,3-benzimidazol-3-ium-1,3-diacetato-κ4O,O′:O′′:O′′′)dysprosium(III)], C11H11DyN4O11
  35. Crystal structure of n-butyl-tris(dicyclo-hexylamido)hafnium(IV), C40H75HfN3
  36. Crystal structure of (E)-1-[1-(3-chloro-4-fluoro-phenyl)ethylidene]-2-(2,4-dinitrophenyl)hydrazine, C28H20Cl2F2N8O8
  37. The crystal structure of ethyl 4-((2-hydroxybenzyl)amino)benzoate, a Schiff base, C16H17NO3
  38. Crystal structure of 3-(2-(4-isobutylphenyl)propanoyl)-1-methylimidazolidine-2,4-dione, C17H22N2O3
  39. Crystal structure of poly[(μ3-2-(pyrazin-2-ylthio)acetato-κ3N:O:S)silver(I)], C6H5AgN2O2S
  40. Crystal structure of (E)-1-(3-((E)-((2-hydroxynaphthalen-1-yl)methylene)amino)phenyl)ethanone O-benzyl oxime, C26H22N2O2
  41. Crystal structure of (E)-2,3-dihydroxybenzaldehyde O-(2-((((E)-1-(2,5-dihydroxyphenyl)ethylidene)amino)oxy)ethyl) oxime monohydrate, C17H20N2O7
  42. Crystal structure of 4-(chloromethyl)-3-nitrobenzoic acid, C8H6ClNO4
  43. Crystal stucture of 4-((10H-phenothiazin-10-yl)methyl)-2,6-di-tert-butylphenol, C27H31NOS
  44. The crystal structure of ethyl 1-(4-nitrophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C13H10F3N3O4
  45. Crystal structure of catena-poly[di-(μ3-oxido-κ3O:O:O)-tetraoxido-(μ2-5′-(pyrazin-2-yl)-1H,2′H-3,3′-bi(1,2,4-triazole)-κ2N:N′)dimolybdenum(VI)], C8H6Mo2N8O6
  46. Crystal structure of (3,6-dioxocyclohexa-1,4-diene-1,4-bis(olato)-κ4O,O′:O′′,O′′′)-bis(tris(2-pyridylmethyl)amine-κ4N,N′,N′′,N′′′))-dizinc(II) bis(hexafluorophosphate(V)), C42H38F12N8O4P2Zn2
  47. Crystal structure of catena-poly[hexakis(μ2-2-acetylphenolato-κ3O:O,O′)trimanganese(II)], C48H42Mn3O12
  48. The crystal structure of 2,2-difluoro-4-(trifluoromethyl)-2,5-dihydro-[1,3,2]dioxaborinino[5,4-c]chromen-3-ium-2-uide, C11H6BF5O3
  49. Crystal structure of methyl (E)-2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazine-1-carboxylate, C13H19N3O3
  50. The crystal structure of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate, C10H15N3O2
  51. Crystal structure of 1,1-bis(η5-adamantylcyclopentadienyl)-3-phenyl-2-trimethylsilyl-2,3-dihydroisotitanazole, C42H55NSiTi
  52. Crystal structure of 2-(4-(2-(4-benzylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C28H29N3O2
  53. Important impurity of Flupirtine – a single crystal study on ethyl (6-amino-5-((ethoxycarbonyl)amino)pyridin-2-yl)(4-fluorobenzyl)carbamate, C18H21FN4O4
  54. Crystal structure of ethyl 3-(4-methoxyphenyl)-1-(2-(4-methoxyphenyl)-2-oxoethyl)-1H-pyrazole-5-carboxylate, C22H22N2O5
  55. Crystal structure of 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate methanol solvate, C37H35N1O10
  56. The crystal structure of the inner salt of 2-[(aminoiminomethyl)amino]ethylcarbamic acid [systematic name: (2-((diaminomethylene)ammonio)ethyl)carbamate], C4H10N4O2
  57. Crystal structure of (8-hydroxy-5-nitroquinolinium) perchlorate – 8-hydroxy-5-nitroquinoline (1/1), C18H13ClN4O10
  58. The crystal structure of (5-methyl-1,2,4-oxadiazol-3-yl)ferrocene, C13H12FeN2O
  59. Crystal structure of methyl 1-(2-(fluorosulfonyl)ethyl)-2-oxocyclopentanecarboxylate, C9H13FO5S
  60. Crystal structure of the triclinic modification of 1-methyl-4-nitroimidzole, C4H5N3O2
  61. Corrigendum
  62. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
Heruntergeladen am 21.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2016-0267/html
Button zum nach oben scrollen