Startseite Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2
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Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2

  • Tao Fu , Jin-Xia Ma , Qing-Lin Li , Ping Wei , Ji-Xing Zhao und Li Zhao EMAIL logo
Veröffentlicht/Copyright: 20. August 2018

Abstract

C16H14Cl2N2O2, monoclinic, P21/c (no. 14), a = 7.9157(6) Å, b = 13.4533(8) Å, c = 14.8459(10) Å, β = 103.651(2)°, V = 1536.31(18) Å3, Z = 4, Rgt(F) = 0.0410, wRref(F2) = 0.1162, T = 296(2) K.

CCDC no.: 1860089

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.

Source of material

All solvents and other reagents were of analytical grade and the title compound was prepared by modification of the reported method [4], [5]. 3,5-Dichlorosalicylaldehyde (191.1 mg, 1 mmol) dissolved in ethanol solution (5 mL) was added to 1-(4-aminophenyl)ethanone O-methyl oxime (164.2 mg, 1 mmol) dissolved in ethanol solution (5 mL). The solution had been stirred at 328 K for 10 h, and the mixture was filtered at room temperature. Some yellow solid was obtained (yield 66.3%, m.p. 377–384 K). Crystals were obtained by slow evaporation in a quiet environment at room temperature. Anal. Calcd. for C16H14Cl2N2O2: C, 56.99%; H, 4.18%; N, 8.31%; Found: C, 56.87%; H, 4.25%; N, 8.27%.

Table 1:

Crystal collection and handling.

Crystal:Block, red
Size:0.22 × 0.18 × 0.17 mm
Wavelength:Mo Kαradiation (λ = 0.71073 Å)
μ:0.43 mm−1
Diffractometer, scan mode:Bruker SMART CCD, ϕ and ω-scan
2θmax, completeness:52.99°, >99%
N(hkl)measured, N(hkl)unique, Rint:11991, 3168, 0.0627
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 2757
N(param)refined:202
Programs:Bruker [1], SHELX [2], OLEX2 [3]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.24332(7)0.22160(3)0.14590(3)0.03503(16)
Cl20.14421(7)−0.16966(3)0.07978(3)0.03444(16)
O10.49137(19)0.15795(8)0.31249(9)0.0287(3)
H10.5616440.1369530.3582520.043
O21.32073(19)0.02804(10)0.89959(9)0.0337(3)
N10.6488(2)0.02689(10)0.43001(9)0.0230(3)
N21.1974(2)0.04531(12)0.81615(10)0.0287(4)
C10.4138(2)0.08144(11)0.26176(11)0.0207(3)
C20.2930(2)0.09937(12)0.17812(11)0.0225(4)
C30.2099(2)0.02362(12)0.12210(11)0.0231(4)
H30.1297610.0374620.0668200.028
C40.2489(2)−0.07352(12)0.15030(11)0.0235(4)
C50.3653(2)−0.09510(12)0.23222(11)0.0240(4)
H50.388583−0.1609290.2499790.029
C60.4491(2)−0.01814(12)0.28910(11)0.0214(4)
C70.5685(2)−0.04118(12)0.37640(11)0.0239(4)
H70.587403−0.1073300.3940910.029
C80.7659(2)0.00524(12)0.51566(11)0.0223(4)
C90.8022(3)−0.08943(13)0.55294(12)0.0310(4)
H90.746378−0.1443150.5211440.037
C100.9209(3)−0.10260(13)0.63699(12)0.0299(4)
H100.943869−0.1664950.6606370.036
C111.0063(2)−0.02266(13)0.68669(11)0.0234(4)
C120.9653(3)0.07256(13)0.64981(12)0.0302(4)
H121.0178120.1277640.6825270.036
C130.8484(3)0.08568(13)0.56588(12)0.0291(4)
H130.8243810.1495810.5424540.035
C141.1361(2)−0.03553(13)0.77589(11)0.0246(4)
C151.1900(3)−0.13686(15)0.81399(13)0.0342(4)
H15A1.300134−0.1325070.8580260.051
H15B1.200152−0.1804220.7643170.051
H15C1.104296−0.1625540.8440250.051
C161.3795(3)0.12249(15)0.93907(13)0.0366(5)
H16A1.4243050.1606140.8952280.055
H16B1.4694840.1127880.9943170.055
H16C1.2840710.1574530.9541520.055

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Discussion

Oximes are compounds which carry a carbon-nitrogen double bond formed by the reactions of aldehydes or ketones with hydroxylamines [6], [7], [8], [9]. Various properties of oxime-type compounds along with their applications in analytical chemistry increased interest [10], [11]. As so far, such oxime-type compounds are used as analytical reagents for the detection and determination of some metal ions [12], [13]. Further more some compounds represent nonlinear optical materials and others show supramolecular architectures [14], [15], [16], [17].

The asymmetric unit (cf. the figure) is built up by C16H14Cl2N2O2 molecules. The crystal structure of the title compound was determined by X-ray crystallography. All bond lengths are in normal ranges. There is a strong intramolecular O1—H1⋯N1 hydrogen bond interaction (d(N1⋯H1) = 1.86 Å, d(O1—H1) = 0.82 Å and d(O1⋯N1) = 2.584 Å) in the title compound.

References

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Received: 2018-07-19
Accepted: 2018-08-03
Published Online: 2018-08-20
Published in Print: 2018-11-27

©2018 Tao Fu 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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