Home Crystal structure of 2,2′-(butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(4-methoxyphenol), C20H24N2O4
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Crystal structure of 2,2′-(butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(4-methoxyphenol), C20H24N2O4

  • Daniel M. Orang’o , Martin O. Onani ORCID logo EMAIL logo , Paul K. Tarus , Samuel T. Lutta and Roger A. Lalancette
Published/Copyright: August 9, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 6

Abstract

C20H24N2O4, monoclinic, P21/n (no. 14), a = 11.0474(3) Å, b = 6.0853(2) Å, c = 13.9881(4) Å, β = 104.271(2)°, V = 911.36(5) Å3, Z = 2, R gt (F) = 0.0290, wR ref (F 2) = 0.0728, T = 100(2) K.

CCDC no.: 1911767

The molecular structure is shown in 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 parallelepiped
Size: 0.35 × 0.16 × 0.09 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.74 mm−1
Diffractometer, scan mode: Bruker SMART Apex-II, φ and ω
θ max, completeness: 66.6°, 98%
N(hkl)measured, N(hkl)unique, R int: 9785, 2698, 0.028
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2539
N(param)refined: 241
Programs: Bruker [1], SHELX [2], Diamond [3]
Table 2:

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

Atom x y z U iso*/U eq
C1 0.64008 (17) 0.9164 (4) 0.13709 (13) 0.0162 (4)
C2 0.57652 (17) 1.1180 (4) 0.12601 (13) 0.0184 (5)
C3 0.59650 (18) 1.2685 (4) 0.05643 (14) 0.0207 (4)
H3A 0.553564 1.405082 0.048317 0.025*
C4 0.67834 (18) 1.2199 (4) −0.00069 (14) 0.0221 (5)
H4 0.690968 1.323514 −0.048090 0.027*
C5 0.74297 (18) 1.0207 (4) 0.01003 (14) 0.0199 (5)
C6 0.72360 (17) 0.8693 (4) 0.07859 (14) 0.0181 (5)
H6 0.766908 0.733040 0.086129 0.022*
C7 0.8705 (2) 0.7766 (4) −0.05657 (15) 0.0302 (5)
H7A 0.920348 0.730498 0.008381 0.045*
H7B 0.923010 0.776059 −0.103758 0.045*
H7C 0.800605 0.674659 −0.078953 0.045*
C8 0.61923 (16) 0.7529 (4) 0.20764 (13) 0.0160 (4)
H8 0.660896 0.615342 0.212042 0.019*
C9 0.52678 (18) 0.6169 (4) 0.33066 (14) 0.0201 (5)
H9A 0.555757 0.668093 0.399719 0.024*
H9B 0.577009 0.486794 0.322409 0.024*
C10 0.39022 (17) 0.5529 (4) 0.31019 (14) 0.0194 (5)
H10A 0.361685 0.500408 0.241300 0.023*
H10B 0.340043 0.683757 0.317511 0.023*
C11 0.36864 (17) 0.3739 (4) 0.37980 (14) 0.0199 (5)
H11A 0.393288 0.428978 0.448467 0.024*
H11B 0.421949 0.245726 0.374869 0.024*
C12 0.23267 (17) 0.3020 (4) 0.35600 (14) 0.0230 (5)
H12A 0.178671 0.431631 0.356440 0.028*
H12B 0.209525 0.236698 0.289134 0.028*
C13 0.15127 (16) 0.2041 (4) 0.49011 (14) 0.0182 (5)
H13 0.115172 0.346668 0.483727 0.022*
C14 0.13610 (16) 0.0626 (4) 0.57031 (13) 0.0166 (4)
C15 0.18869 (17) −0.1481 (4) 0.58234 (14) 0.0179 (5)
C16 0.18253 (17) −0.2721 (4) 0.66495 (13) 0.0192 (5)
H16 0.218728 −0.414604 0.673975 0.023*
C17 0.12403 (17) −0.1884 (4) 0.73355 (14) 0.0192 (5)
H17 0.121833 −0.272869 0.790210 0.023*
C18 0.06823 (17) 0.0180 (4) 0.72087 (14) 0.0179 (4)
C19 0.07448 (16) 0.1445 (4) 0.63968 (13) 0.0171 (4)
H19 0.037210 0.286097 0.630955 0.021*
C20 −0.05252 (18) 0.2871 (4) 0.78128 (15) 0.0239 (5)
H20A 0.009102 0.405347 0.787026 0.036*
H20B −0.098280 0.304664 0.832568 0.036*
H20C −0.111223 0.293737 0.716170 0.036*
N1 0.54579 (14) 0.7912 (3) 0.26385 (11) 0.0188 (4)
N2 0.21211 (14) 0.1411 (3) 0.42787 (11) 0.0201 (4)
O1 0.49423 (13) 1.1699 (3) 0.18013 (10) 0.0244 (4)
H1 0.490835 1.066750 0.219273 0.037*
O2 0.82349 (13) 0.9927 (3) −0.04984 (10) 0.0266 (4)
O3 0.24919 (12) −0.2351 (3) 0.51775 (9) 0.0221 (3)
H3 0.250825 −0.142609 0.473486 0.033*
O4 0.00990 (12) 0.0797 (3) 0.79304 (9) 0.0215 (4)

Source of material

The title compound was prepared from a 2:1 reaction ratio of substituted salicylaldehyde 2-hydroxy-5-methoxybenzaldehyde with 1,4-diaminobutane in dry ethanol under reflux for 1 h. The title compound was obtained as a yellow solid with yield = 96%. Elemental analysis for C20H24N2O4 (256.42 g/mol), Calculated: C, 49.77%; H, 5.64; N, 5.81; Found: C, 50.00%; H, 5.72; N, 5.64. Single crystals suitable for X-ray diffraction (XRD) studies were obtained after four weeks by slow diffusion and evaporation of hexane into a concentrated solution of the compound in DCM.

Experimental details

Crystal evaluation and data collection were done on a Bruker SMART 1000 CCD diffractometer with Mo Kα radiation (λ = 0.71073 Å) equipped with an Oxford Cryostream low temperature apparatus operating at 100(1) K. The structure was solved by direct method using the SHELXS [2] program and refined with SHELXL [2]. All hydrogen atoms were placed in idealized positions and refined in riding models with U iso assigned the values of 1.2 times or 1.5 times those of their parent atoms and the distances of C–H were constrained to 0.95 Å for all the aromatic H atoms and 0.99 for CH2 protons or 0.84 Å for the hydroxy group H atoms, respectively. The idealised tetrahedral OH refined as rotating group. The visual crystal structure information was performed using Diamond [3].

Comment

The salicylaldimine ligands have drawn much interest from many researchers because they can easily bind to many transition metals like nickel, palladium, copper, manganese, iron, zinc and ruthenium [4], [5], [6], [7], [8], [9]. These complexes have found a wide range of applications in catalysis like olefin polymerization and (co)polymerization of substituted norbornene, ethylene polymerization and (co)polymerization [10], [11], [12], [13], ring-opening and ring-closing metathesis polymerization [9, 14–16].

The asymmetric unit of the title compound contains one salicylaldimine molecule. In the structure, the aminomethyl methoxyphenol moieties are on either sides of the butyl linker and are almost co-planar with a dihedral angle of 12.78(3)°.

Corresponding author: Martin O. Onani, Department of Chemistry, Faculty of Natural Sciences, University of the Western Cape, Private Bag X17, Bellville 7535, Republic of South Africa, E-mail:

Acknowledgements

We sincerely appreciate the University of the Western Cape and the National Research Foundation of South Africa (Grant number: 105894) for their financial support for the project.

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

  2. Research funding: University of the Western Cape and the National Research Foundation of South Africa.

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

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Received: 2021-07-06
Accepted: 2021-07-20
Published Online: 2021-08-09
Published in Print: 2021-12-20

© 2021 Daniel M. Orang’o et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  67. Synthesis and crystal structure of 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate monohydrate, C20H19NO10S
  68. The crystal structure of 3-amino-5-carboxypyridin-1-ium bromide, C6H7BrN2O2
  69. The crystal structure of (2-hydroxy-5-methyl-phenyl)-(1H-pyrazol-4-yl)-methanone hemihydrate, C11H10.5N2O2.5
  70. Crystal structure of tetraaqua-(2-(4-formylphenoxy)acetato-k1O)cadmium(II), C18H22O12Cd
  71. Crystal structure of diethyl 6,12-dimethyl-3,9-di-p-tolyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5-dicarboxylate, C32H38N2O4
  72. Crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl)ethylidene)-4-hydroxy – tetrahydrofuran (2/1), C17H16ClFN2O2.5
https://doi.org/10.1515/ncrs-2021-0273
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Redetermination of the crystal structure of 3-bromonitrobenzene at 200 K, C6H4BrNO2 – temperature effects on cell constants
  4. Crystal structure of (E)-ethyl 2-((4-oxo-4H-chromen-3-yl)methyleneaminooxy)acetate, C14H13NO5
  5. Crystal structure of (8R,10R,14R, Z)-2-((3–Fluoropyridin-4-yl) methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6, 6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a] phenanthren-3-one, C36H52FNO3
  6. Crystal structure of [6,6′-((1E,1′E)-(propane-1,3- diylbis(azaneylylidene))bis(methaneylylidene)) bis(3-chlorophenol)-κ4N,N′,O,O′] copper(II), C17H14Cl2CuN2O2
  7. The crystal structure of 6-amino-2-carboxypyridin-1-ium bromide, C6H7BrN2O2
  8. Redetermination of the crystal structure of bis[N,N′-ethylenebis(acetylacetoniminato)nickel(II)] sodium perchlorate, C24H36ClN4NaNi2O8
  9. The crystal structure of 3-methyl-2,6-dinitrophenol, C7H6N2O5
  10. The crystal structure of 5-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  11. Crystal structure of trans-tetraaqua-bis{2-carboxy-4-((5-carboxypyridin-3-yl)oxy)benzoato-κ1 N}cobalt(II) dihydrate C28H28O20N2Co
  12. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-(p-tolyl)furan, C23H23BrO2
  13. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(benzo[d][1,3]dioxol-5-ol ato-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV)-dichloromethane(1/1), C27H25N3O10Ti
  14. Crystal structure of (((1E,1′E)-1,2-phenylenebis(methaneylylidene))bis(hydrazin-1-yl-2-ylidene))bis(aminomethaniminium) dinitrate C10H16N10O6
  15. Crystal structure of catena-poly[triaqua-(μ 2-1,3-di(1H-imidazol-1-yl)propane-κ 2 N:N′)-(4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ 1 O)nickel(II)]N,N′-dimethylformamide (1/1), C28H35N8O8Ni
  16. The crystal structure of 3,3′-[1,4-phenylenebis(methylene)]bis(1-ethenyl-1H-imidazol-3-ium) dichloride – dichloromethane – water (1/1/1), C19H24Cl4N4O1
  17. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C13H22F12N4P2
  18. Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)tin(IV), C12H8Cl4Sn
  19. Synthesis and crystal structure of 4-acetylpyrene, C18H12O
  20. Crystal structure of 2,2′-(butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(4-methoxyphenol), C20H24N2O4
  21. The crystal structure of (E)-2-(((5-((triphenylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C27H21N3OS2Sn
  22. Crystal structure of diaqua-bis(μ2-6-phenylpyridine-2-carboxylate-κ3N,O:O)-bis(6-phenylpyridine-2-carboxylato-κ2N,O)lead(II) – N,N-dimethylformamide – water (1/2/4), C54H58N6O16Pb2
  23. Crystal structure of methyl 4-acetoxy-3-methoxybenzoate, C11H12O5
  24. Crystal structure of 2,2′-(propane-1,3-dilylbis(azaneylylidene))bis(methanylylidene)bis(4-methylphenol), C19H22N2O2
  25. Crystal structure of dichlorido-bis(4-methylphenyl-κC1)tin(IV), C14H14Cl2Sn
  26. Crystal structure of methyl (E)-3-(4-acetoxyphenyl)acrylate, C12H12O4
  27. The crystal structure of bis(benzoato-κ2 O,O′)-(2,9-dimethyl-1,10-phenanthroline-κ2 N,N′)-copper(II), C28H22CuN2O4
  28. Crystal structure of (8R,10R,14R,Z)-12-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one–water (2/1), C37H56NO4.5
  29. Crystal structure of dimethyl-bis(4-bromophenyl-κC1)tin(IV), C14H14Br2Sn
  30. The crystal structure of the cocrystal di-μ2-chlorido-octamethyl-di-μ3-oxido-bis(2,3,4,5-tetrafluorobenzoato-κ2 O,O′)tetratin(IV) ─ octamethyl-di-μ3-oxido-bis(μ2-2,3,4,5-tetrafluorobenzoato-κ2 O:O′)-bis(μ2-2,3,4,5-tetrafluorobenzoato-κ2 O:O;O′)tetratin(IV) C58H54Cl2F24O16Sn8
  31. Crystal structure of 3-iodo-N 2-(2-methyl-1-(methylsulfonyl)propan-2-yl)-N 1-(2-methyl-4-(perfluoropropan-2-yl)phenyl)phthalamide, C23H22F7I1N2O4S1
  32. Crystal structure of 1-(2-(4-bromophenyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)-naphthalen-2-ol – dichloromethane – dimethyl sulfoxide (1/1/1), C28H18BrNO·CH2Cl2·C2H6SO
  33. Crystal structure of [meso-5,7,7,12,14,14,-hexamethyl-1,4,8,11-tetraazacyclotetradecane]nickel(II) diperchlorate – dimethylsulphoxide (1/2), C20H48Cl2N4NiO10S2
  34. Crystal structure of 1,1′-(1,3-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S) palladium(II), C26H18N6PdS4
  35. The crystal structure of bis(6-phenylpyridine-2-carboxylato-κ2 N,O)copper(II), C24H16N2O4Cu
  36. Crystal structure of dichlorido-bis(4-chlorophenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C48H38As2Cl4O2Sn
  37. Crystal structure of (4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane-κ 8 N 2, O 6) potassium cyclopentadienide, [K([2.2.2]crypt)]Cp, C23H41KN2O6
  38. The crystal structure of bis(2-oxidopyridin-1-ium-3-carboxylato-κ2O,O′)-(phenantroline-κ2N,N′)manganese(II) - methanol (1/3), C27H28N4O9Mn
  39. Crystal structure of 4-(dimethylamino)pyridinium dibromido-tris(4-chlorophenyl-κC)stannate(IV), C25H23Br2Cl3N2Sn
  40. Crystal structure of (3E,5E)-1-(4-cyanobenzenesulfonyl)-3,5-bis(3-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C27H20Cl2F2N2O3S
  41. Crystal structure of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-trifluoromethyl)benzenesulfonyl)piperidin-4-one, C26H18F5NO3S
  42. Crystal structure of chlorido-(4-methyl-2-((phenylimino)methyl)phenolato-κ2 N,O)-(pyridine-κ1 N)platinum(II), C19H17ClN2OPt
  43. Crystal structure of (4-methylbenzyl)(triphenyl)phosphonium chloride dihydrate, C26H28ClO2P
  44. The crystal structure of poly[μ2-chlorido-(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′silver(I)], C12H12AgClN2
  45. Crystal structure of poly[(μ4-benzene-1,2,4,5-tetracarboxylato)-bis(μ2-adipohydrazide)dicadmium], C11H15N4O6Cd
  46. The crystal structure of (E)-N′-(butan-2-ylidene)isonicotinohydrazide 0.5 hydrate C10H13N3O·0.5H2O
  47. The crystal structure of bis(6-phenylpyridine-2-carboxylate-κ2 N,O)-(2,2′-bipyridine-κ2 N,N′)zinc(II) monohydrate, C34H26N4O5Zn
  48. The crystal structure of (1R *,2S *)-1,2-bis(2-fluorophenyl)-3,8-dimethoxyacenaphthene-1,2-diol, C26H20F2O4
  49. Crystal structure of catena-poly[(μ2-1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzotriazole-κ2N:N′)-(nitrato-κ2O,O′)silver (I)], C13H15Ag1N6O3
  50. The crystal structure of [(phenantroline-κ2 N,N′)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)cobalt(II)]monohydrate, C36H26N4O5Co
  51. Crystal structure of (1E)-N′-[(1E)-1-(4-chlorophenyl)ethylidene]-2-[1-(4-chlorophenyl)ethylidene]hydrazine-1-carbohydrazonamide, C 17 H 17 Cl 2 N 5
  52. The crystal structure of (E)-2-((tert-butylimino)methyl)-4-chlorophenol, C11H14ClNO
  53. Crystal structure of all-cis-2,4,6-trihydroxycyclohexane- 1,3,5-triaminium chloride sulfate, C6H18ClN3O7S
  54. Crystal structure of dichlorido-bis(dimethyl sulfoxide-κO)bis(4-methylphenyl-κC 1)tin(IV), C18H26Cl2O2S2Sn
  55. Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)(2,2′-bipyridyl-κ 2 N,N′)tin(IV), C22H16Cl4N2Sn
  56. Redetermination of the crystal structure of (E)-5-bromo-2-hydroxybenzaldehyde oxime, C 7 H 6 BrNO 2
  57. The crystal structure of (E)-amino(2-(4-methylbenzylidene)hydrazineyl)methaniminium 4-methylbenzoate, C9H13N4 + C8H7O2 −
  58. Crystal structure of 2-chloro-3-(isopentylamino)naphthalene-1,4-dione, C 15 H 16 ClNO 2
  59. The crystal structure of bis(2-acetyl-5-methoxyphenyl)carbonate 1.5 hydrate, C19H18O7
  60. The crystal structure of poly[(μ 4-4,4′-(azanediylbis(methylene))dibenzoato-κ 4 O:N:O′:Oʺ)zinc(II)], C16H13NO4Zn
  61. The crystal structure of catena-poly[(1,10-phenanthroline-k2N,N′)-(μ3-tetraoxidomoybdato(VI)-k3O:O′:O″)manganese(II)] C12H8N2O4MoMn
  62. Crystal structure of catena-poly[(4-hydroxyl-5-(methoylcarbonyl)thiophene-2-carboxylato-κ1 O)-(μ2-piperazine-1,4-diylbis(pyridin-4-ylmethanone)-κ2 N:N′)silver(I)] monohydrate, C23H23AgN4O8S
  63. Crystal structure of bis(4-bromo-2-(((3-bromopropyl)imino)methyl)phenolato-κ2N,O)-oxido-vanadium(IV), C20H20Br4N2O3V
  64. The crystal structure of (2a′S,2a1′S,3R,5a′S,7′R)-5-(furan-3-yl)-2a′,2a1′-dihydroxy-7′-methyldecahydro-2H-spiro[furan-3,6′-naphtho[1,8-bc]furan]-2,2′(2a′H)-dione, C19H22O7
  65. The crystal structure of 3-bromopicolinic acid, C6H4BrNO2
  66. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S,S) platinum(II), C26H18N6PtS4
  67. Synthesis and crystal structure of 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate monohydrate, C20H19NO10S
  68. The crystal structure of 3-amino-5-carboxypyridin-1-ium bromide, C6H7BrN2O2
  69. The crystal structure of (2-hydroxy-5-methyl-phenyl)-(1H-pyrazol-4-yl)-methanone hemihydrate, C11H10.5N2O2.5
  70. Crystal structure of tetraaqua-(2-(4-formylphenoxy)acetato-k1O)cadmium(II), C18H22O12Cd
  71. Crystal structure of diethyl 6,12-dimethyl-3,9-di-p-tolyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5-dicarboxylate, C32H38N2O4
  72. Crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl)ethylidene)-4-hydroxy – tetrahydrofuran (2/1), C17H16ClFN2O2.5
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