Startseite Crystal structure of (4-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C29H52Cl2N4NiO9
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Crystal structure of (4-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C29H52Cl2N4NiO9

  • Fang Liu , Guo-Kai Jia und Guang-Chuan Ou EMAIL logo
Veröffentlicht/Copyright: 8. August 2018

Abstract

C29H52Cl2N4NiO9, monoclinic, P21/n (no. 14), a =10.8347(19) Å, b = 14.502(3) Å, c = 21.731(4) Å, β = 93.344(2)°, V = 3408.6(10) Å3, Z = 4, Rgt(F) = 0.0360, wRref(F2) = 0.1009, T = 296(2) K.

CCDC no.: 1569959

The crystal structure is shown in the figure. Hydrogen atoms are omitted for clarity. 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:Prism, blue
Size:0.45 × 0.42 × 0.30 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.78 mm−1
Diffractometer, scan mode:Bruker SMART, φ and ω-scans
θmax, completeness:27.5°, >97% (up to 25.2°, >99%)
N(hkl)measured, N(hkl)unique, Rint:37399, 7623, 0.019
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 6625
N(param)refined:419
Programs:Bruker programs [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
Ni10.26359(2)0.52040(2)0.16501(2)0.02486(8)
Cl10.82771(6)0.82560(4)0.19051(3)0.05458(16)
Cl2−0.34104(7)0.02911(5)0.00498(4)0.0705(2)
N10.09651(14)0.51940(11)0.10828(7)0.0305(3)
H1C0.11590.48460.07140.037*
N20.27869(14)0.65691(10)0.13539(7)0.0295(3)
H2C0.23890.69620.16510.035*
N30.42254(14)0.53193(11)0.22709(7)0.0294(3)
H3A0.45650.46950.23130.035*
N40.16406(13)0.53492(10)0.24460(7)0.0265(3)
H4D0.15030.60120.24990.032*
O10.29848(12)0.36685(9)0.16072(6)0.0344(3)
O1W0.34802(17)0.24713(12)0.25914(8)0.0539(4)
H1WB0.322(2)0.2800(17)0.2283(9)0.065*
H1WA0.4210(13)0.2635(19)0.2701(11)0.065*
O20.34195(13)0.46143(9)0.08699(6)0.0351(3)
O30.21761(13)0.18276(10)0.08573(6)0.0397(3)
O40.17587(14)0.28523(10)0.00549(6)0.0389(3)
O50.7527(2)0.8441(2)0.23994(11)0.0928(7)
O60.9437(2)0.8692(2)0.19691(14)0.1018(9)
O70.7664(3)0.8636(4)0.13739(14)0.1602(18)
O80.8442(4)0.7349(2)0.1815(3)0.203(3)
C10.07826(19)0.61579(15)0.08696(10)0.0403(5)
H1A0.03600.65060.11750.048*
H1B0.02740.61650.04870.048*
C20.2013(2)0.65943(15)0.07704(9)0.0397(5)
H2A0.24220.62630.04520.048*
H2B0.18950.72280.06360.048*
C30.40550(18)0.69357(13)0.12869(9)0.0335(4)
H30.44540.65570.09820.040*
C40.4040(2)0.79333(16)0.10613(12)0.0501(6)
H4A0.35950.79690.06670.075*
H4B0.48730.81420.10240.075*
H4C0.36420.83160.13510.075*
C50.48196(19)0.68724(14)0.18932(9)0.0362(4)
H5A0.43280.71230.22130.043*
H5B0.55320.72720.18650.043*
C60.52901(17)0.59238(14)0.21085(9)0.0341(4)
C70.59570(19)0.54337(16)0.16040(11)0.0437(5)
H7A0.63470.48860.17690.066*
H7B0.65730.58360.14510.066*
H7C0.53720.52710.12730.066*
C80.62207(19)0.60658(18)0.26621(11)0.0472(5)
H8A0.58630.64590.29590.071*
H8B0.69590.63460.25250.071*
H8C0.64220.54800.28480.071*
C90.37464(17)0.55461(15)0.28784(9)0.0351(4)
H9A0.36340.62080.29110.042*
H9B0.43400.53540.32050.042*
C100.25306(17)0.50647(15)0.29512(9)0.0340(4)
H10A0.26480.44020.29400.041*
H10B0.22130.52250.33450.041*
C110.04105(17)0.48930(13)0.24930(9)0.0316(4)
H110.05370.42240.25030.038*
C12−0.0210(2)0.51756(18)0.30777(10)0.0472(5)
H12A0.03440.50620.34310.071*
H12B−0.09520.48230.31120.071*
H12C−0.04110.58200.30580.071*
C13−0.04677(17)0.51258(14)0.19390(9)0.0336(4)
H13A−0.05130.57920.19070.040*
H13B−0.12850.49100.20290.040*
C14−0.01813(17)0.47499(14)0.13036(9)0.0343(4)
C15−0.1293(2)0.4952(2)0.08481(11)0.0511(6)
H15A−0.15090.55920.08720.077*
H15B−0.19850.45810.09520.077*
H15C−0.10780.48080.04370.077*
C160.0032(2)0.37139(16)0.13215(12)0.0488(5)
H16A0.01330.34920.09110.073*
H16B−0.06670.34160.14880.073*
H16C0.07630.35800.15770.073*
C170.33519(16)0.38038(13)0.10742(8)0.0295(4)
C180.37371(18)0.30143(13)0.06555(9)0.0333(4)
C190.5133(2)0.31096(17)0.05644(12)0.0490(5)
H19A0.53520.26900.02410.059*
H19B0.52950.37320.04260.059*
C200.5958(2)0.2913(2)0.11373(15)0.0651(7)
H20A0.57150.32970.14690.098*
H20B0.68020.30420.10550.098*
H20C0.58800.22770.12500.098*
C210.34589(19)0.20577(14)0.09103(10)0.0377(4)
H21A0.39170.16010.06910.045*
H21B0.37450.20330.13410.045*
C220.3028(2)0.31099(16)0.00260(9)0.0407(5)
H22A0.30760.3744−0.01130.049*
H22B0.34130.2722−0.02720.049*
C230.1700(2)0.19155(14)0.02419(9)0.0377(4)
H230.22030.1543−0.00240.045*
C240.0396(2)0.15631(14)0.01918(9)0.0379(4)
C25−0.0079(2)0.11880(17)−0.03608(11)0.0491(5)
H250.03960.1195−0.07040.059*
C26−0.1247(2)0.08056(18)−0.04062(12)0.0551(6)
H26−0.15580.0556−0.07780.066*
C27−0.1944(2)0.07955(15)0.00986(12)0.0462(5)
C28−0.1507(2)0.11636(17)0.06520(12)0.0497(5)
H28−0.19900.11580.09920.060*
C29−0.0330(2)0.15441(16)0.06931(10)0.0445(5)
H29−0.00250.17920.10660.053*

Source of material

An acetonitrile solution (20 mL) of [NiL](ClO4)2 (0.270 g, 0.5 mmol) (L = 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane) was added to a solution of 4-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylic acid (0.270 g, 1.0 mmol) and NaOH (0.04 g, 1.0 mmol) in the minimum amount of water. After a few days, blue crystals were separated in ∼32% yield. Anal. Calcd. for C29H52Cl2N4NiO9: C, 47.69; H, 7.17; N, 7.67%. Found: C, 47.25; H, 7.51; N, 7.89%. IR data (cm−1, KBr): 3456(m), 3209(s), 2962(m), 1545(s), 1450(s), 1090(s).

Experimental details

All the hydrogen atoms of the ligands were placed in calculated positions with fixed isotropic thermal parameters and included in the final stage of refinement. The Uiso (H) values of methyl groups were set to 1.5Ueq(C) and the Uiso values of all other hydrogen atoms were set to 1.2Ueq(C, N).

Discussion

Ketal compounds are subjects of great interest because they are usually used as a protection of carbonyl or synthetic intermediates [4], and have been widely applied in fragrance and flavors as well as a new type of spices.

X-ray crystal structural analysis reveals that the title compound contains one complex cation [Ni(C16H36N4)(C13H14O4Cl)]+, one anion [ClO4], and one water molecule. Each Ni(II) ion lies on a general position of the monoclinic space group and is coordinated by four macrocyclic nitrogen atoms of L in a folded conformation and two carboxylate oxygen atoms of the anionic 4-(chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato ligand. The Ni-N bond lengths [2.090(6)–2.131(6) Å] are slightly shorter than the Ni-O bond lengths [2.120(4) and 2.261(4) Å]. Neighbouring cations and anions are discrete, connected to each other through hydrogen bonds between the carboxylate oxygen atom of 4-(chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato ligand and water and nitrogen atom of adjacent cation, forming a one-dimensional chain.

Acknowledgements

This work was financially Supported by the NSFC (51772091), the Scientific Research Fund of Hunan Education Department (17A081) and the Science and Technology Innovative plan of Hunan (2017).

References

Bruker: APEX3, SAINT-Plus, XPREP. Bruker AXS Inc., Madison, Wisconsin, USA (2016).Suche in Google Scholar

Sheldrick, G. M.: SHELXT – Integrated space-group and crystal-structure determination. Acta Crystallogr. A71 (2015) 3–8.10.1107/S2053273314026370Suche in Google Scholar PubMed PubMed Central

Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

Ono, D.; Yamamura, S.; Nakamura, M.: Preparation and properties of bis(sodium sulfate) types of cleavable surfactants derived from diethyl tartrate. J. Oleo. Sci. 54 (2005) 51–57.10.5650/jos.54.51Suche in Google Scholar

Received: 2018-05-22
Accepted: 2018-07-26
Published Online: 2018-08-08
Published in Print: 2018-11-27

©2018 Fang Liu et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of di-μ2-aqua-tetraaqua-bis(4-(1H-1,2,4-triazol-1-yl)benzoato-κN)disodium(I) C18H24N6Na2O10
  3. Crystal structure of diaqua-bis(2-bromo-4-chloro-6-formylphenolato-κ2O,O′)cobalt(II), C16H16Cl2CrN3O7
  4. Crystal structure of catena-poly[(μ2-1-(4-(1H-pyrazol-1-yl)phenyl)ethan-1-one-κ2N:O)-bis(1,1,1-trifluoro-4-oxo-4-(thiophen-2-yl)but-2-en-2-olato-κ2O,O′)copper(II)], C27H18CuF6N2O5S2
  5. Crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C18H15F2NO5
  6. Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6
  7. Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2
  8. Crystal structure of 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine - trichloromethane (1/2), C98H84Cl6N8O8
  9. Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5
  10. Crystal structure of catena-poly[(μ2-3,3′-thiodipropionato-κ2O:O′)-(bipyridine-κ2N,N′)copper(II)] C16H16CuN2O4S
  11. Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5
  12. Crystal structure of (4-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C29H52Cl2N4NiO9
  13. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5
  14. Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2
  15. Crystal structure of catena-poly[diaqua-bis(μ2-3,5-di(1H-1,2,4-triazol-1-yl)benzoate-κ2N:N′)cobalt(II))] 2.5 hydrate, C22H23CoN12O8.50
  16. The crystal structure of dichlorido(1,3-dimesityl-1H-3λ4-imidazol-2-yl)(morpholine-κN)palladium(IV), C25H33Cl2N3OPd
  17. Crystal structure of catena-poly[bis(4,4′-dipyridylaminium-kN)-(μ2-germanowolframato-κ2O:O′)-(2,2′-bipyridine-κ2N,N′)copper(II)] with a Keggin-type heteropolyoxoanion, [Cu(C10H8N2)(C10H10N3)2][GeW12O40] ⋅ H2O
  18. Crystal structure of diaqua-(N-(1-(pyrazin-2-yl)ethylidene)pyridin-1-ium-4-carbohydrazonate-κ3N,N′,O)-tris[nitrato-κ2O,O′)lanthanum(III), C12H15N8O12La
  19. The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8
  20. Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8
  21. Crystal structure of (Z)-2-bromo-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H27BrO2
  22. Crystal structure of 2-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetic acid, C10H9N3O4
  23. Crystal structure of 4,4′-(1,4-phenylene)bis(1H-imidazol-3-ium)bis(2-carboxybenzoate), C30H26N4O8
  24. Crystal structure of 4,4′-(4,10-diphenyl-4,10-dihydropyreno[4,5-d:9,10-d′]diimidazole-5,11-diyl)bis(N,N-diphenylaniline), C66H44N6
  25. Crystal structure of catena-poly[diaqua-bis(μ2-5-(3-(1H-imidazol-5-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)], C20H18CoN12O2
  26. Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5
  27. Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2
  28. Crystal structure of poly[(μ2-2-carboxy-5-nitroisophthalato-κ2O:O′)-(μ2-4-((1H-imidazol-1-yl)methyl)pyridine-κ2N:N′)zinc(II)], C18H12N4O8Zn
  29. Crystal structure of bis(1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)tetraiodidodicadmium(II), [Cd2(C13H15N5)2I4]
  30. Crystal structure of tetramethylammonium bis(acetato-κ1O)-tetrakis(μ3-3-((hydroxyimino)methyl)-5-methoxy-2-oxidobenzoate-κ5O,O′:O′,N:O′′)tetrazinc(II) — N,N′-dimethylformamide — water (1/2/2), C62H96Zn4N10O28
  31. Crystal structure of poly[(μ4-5-tert-butylisophthalato-κ4O:O′:O′′:O′′′)-(1,3-dimethyl-2-imidazolidinone-κO)zinc(II)] C17H22N2O5Zn
  32. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′]-[(pyridine-2,6-dicarboxylato-κ2O,N)]cadmium(II)–methanol (1:3) C34H36CdN8O7
  33. The crystal structure of bis(1H-benzo[d]imidazol-2-amine-κN)-diiodidocadmium(II), C14H14CdI2N6
  34. Crystal structure of tetrakis(1H-benzimidazol-2-amine)-κN)-bis(μ2-sulfonato-κ2O:O′)dizinc(II) - methanol (1/1), C30H36N12O10S2Zn2
  35. Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO
  36. Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5
  37. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-3-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)zinc(II)], C17H16I2N4OZn
  38. Crystal structure of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile, C26H18F2N2O3S
  39. Crystal structure of bis(acetato-κ1O)-bis(1-(pyridin-2-yl)ethan-1-one oxime-κ2N,N′)zinc(II), C18H22N4O6Zn
  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
  48. Crystal structure of 2-(bis(4-fluorophenyl)methylene)hydrazine-1-carbothioamide, C14H11F2N3S
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