Startseite Redetermination of the crystal structure of N′-(3-ethoxy-2-hydroxybenzylidene)-4-fluorobenzohydrazide monohydrate, C16H17FN2O4
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Redetermination of the crystal structure of N′-(3-ethoxy-2-hydroxybenzylidene)-4-fluorobenzohydrazide monohydrate, C16H17FN2O4

  • Kong Mun Lo , See Mun Lee und Edward R.T. Tiekink ORCID logo EMAIL logo
Veröffentlicht/Copyright: 9. September 2019
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 235 Heft 2

Abstract

C16H17FN2O4, monoclinic, P21/c (no. 14), a = 9.23280(10) Å, b = 12.9330(2) Å, c = 12.3477(2) Å, β = 97.383(1)°, V = 1462.19(4) Å3, Z = 4, Rgt(F) = 0.0318, wRref(F2) = 0.0861, T = 100(2) K.

CCDC no.: 1949158

The molecular structures are shown in the 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 prism
Size:0.13 × 0.07 × 0.03 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:0.96 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:67.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:17553, 2601, 0.039
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2353
N(param)refined:276
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
F10.17356(8)0.75207(6)1.22153(6)0.0247(2)
O10.43989(11)0.94056(7)0.82362(7)0.0251(2)
O20.70132(10)0.91296(7)0.56094(7)0.0211(2)
H2O0.651(2)0.9037(16)0.6122(16)0.042(5)*
O30.86944(10)0.91781(7)0.40723(7)0.0214(2)
N10.51705(11)0.77511(9)0.80658(8)0.0182(2)
H1N0.5191(18)0.7126(15)0.8264(13)0.029(4)*
N20.58967(11)0.79844(9)0.71832(8)0.0191(2)
C10.44589(13)0.85001(10)0.85485(9)0.0185(3)
C20.37537(13)0.81800(10)0.95217(9)0.0180(3)
C30.33094(13)0.71721(10)0.97067(9)0.0186(3)
H30.3456(16)0.6637(12)0.9204(12)0.019(3)*
C40.26254(13)0.69411(10)1.06164(10)0.0191(3)
H40.2337(18)0.6235(14)1.0741(12)0.027(4)*
C50.24076(13)0.77353(10)1.13235(9)0.0191(3)
C60.28506(14)0.87364(10)1.11818(10)0.0206(3)
H60.2698(17)0.9256(13)1.1721(12)0.024(4)*
C70.35205(14)0.89561(10)1.02650(10)0.0201(3)
H70.3833(17)0.9652(13)1.0161(12)0.023(4)*
C80.65234(13)0.72022(10)0.68004(10)0.0194(3)
H80.6457(17)0.6521(13)0.7102(12)0.022(4)*
C90.73890(13)0.72823(10)0.58954(9)0.0188(3)
C100.76169(13)0.82141(10)0.53635(9)0.0180(3)
C110.85275(13)0.82294(10)0.45288(9)0.0186(3)
C120.91745(14)0.73239(10)0.42304(10)0.0203(3)
H120.9816(19)0.7337(13)0.3685(14)0.030(4)*
C130.89223(14)0.63949(10)0.47478(10)0.0221(3)
H130.9351(17)0.5769(13)0.4534(12)0.022(4)*
C140.80462(14)0.63723(10)0.55698(10)0.0213(3)
H140.7899(17)0.5719(13)0.5950(12)0.025(4)*
C150.97702(14)0.92450(10)0.33209(10)0.0201(3)
H15A0.9538(16)0.8763(12)0.2733(12)0.020(3)*
H15B1.0717(17)0.9103(12)0.3719(12)0.021(4)*
C160.97373(15)1.03313(11)0.28903(11)0.0236(3)
H16A0.8793(18)1.0508(12)0.2475(13)0.025(4)*
H16B1.0481(19)1.0381(14)0.2387(14)0.036(4)*
H16C0.9957(18)1.0839(13)0.3498(13)0.029(4)*
O1W0.51710(10)0.55211(7)0.85542(8)0.0224(2)
H1W0.581(2)0.5425(14)0.9103(16)0.034(5)*
H2W0.535(2)0.5086(19)0.8022(18)0.059(6)*

Source of material

All chemicals and solvents were used as purchased and used without further purification. The melting point was determined using a Electrothermal digital melting point apparatus and was uncorrected. The IR spectrum was obtained on a Perkin-Elmer RX1 spectrophotometer as a Nujol mull in a KBr cell from 4000 to 400 cm−1. The 1H NMR spectrum was recorded at room temperature in CDCl3 solution on a Bruker AVN FT-NMR 400 MHz NMR spectrometer with chemical shifts relative to tetramethylsilane.

3-Ethoxysalicylaldehyde (Sigma Aldrich, 0.17 g, 1 mmol) in methanol (10 mL) was added to a hot stirring methanol solution (20 mL) of 4-fluorobenzoic hydrazide (Sigma Aldrich, 0.15 g, 1 mmol). The mixture was refluxed for 2 h. After filtration, the filtrate was evaporated slowly until colourless crystals were formed. The crystal was washed with methanol and air-dried. Yield: 0.20 g (65.7%) M.pt: 379–381 K. IR (cm−1): 3561 (br) ν(O—H), 1648 (s) ν(C—O), 1605 (s) ν(C—N), 1605 (s) ν(C—N), 1078 (s) ν(C—O). 1H NMR (CDCl3, ppm): δ 1.39 (t, J = 6.9 Hz, 3H, CH3), 3.97–4.08 (m, 2H, OCH2), 6.60–7.11 (m, 4H, Ph-H), 8.05–8.10 (m, 3H, Ph-H), 8.66 (s, 1H, HCN), 10.90 (s, 1H, NH), 12.10 (s, 1H, OH), water-H not observed.

Experimental details

All of the H-atoms were located in a difference Fourier map and were refined without restraint.

Comment

The redetermination of the crystal structure of the title hydrazone compound (I) [5] was conducted in the context of on-going structural studies of related Schiff base molecules [6], [7] and their organotin compounds [8], [9], [10]. With the combined advantages of Cu Kα radiation and low temperature, it was possible to refine all atoms in the molecule with the key result of improved standard uncertainty values. In addition, a full description of the molecular packing of (I) is now described, an analysis which is complimented by an evaluation of the calculated Hirshfeld surfaces along with the full and delineated fingerprint plots [11], [12].

The crystallographic asymmetric unit of (I) comprises the Schiff base molecule and a water molecule, as shown in the figure (70% displacement ellipsoids). The configuration about the imine-N2—C8 [1.2852(17) Å] bond is E. The five non-hydrogen atoms comprising the central chromophore, i.e. C(=O)N(H)N=C, are strictly planar with the r.m.s. deviation being 0.0033 Å. The dihedral angles formed between the central plane and the least-squares planes through the flanking hydroxy- and fluoro-phenyl rings are 4.35(9) and 23.93(6)°, respectively, indicating almost co-planar and inclined orientations. The dihedral angles formed between the outer rings is 24.26(5)°. The co-planar relationship between the central chromophore and hydroxyphenyl ring allows for the formation of an intramolecular hydroxy-O—H⋯N(imine) hydrogen bond [O2—H2o⋯N2: O2—H2o = 0.841(19) Å, H2o⋯N2 = 2.02(2) Å, O2⋯N2 = 2.7473(14) Å with angle at H2o = 144.4(19)°].

The crystal of (I) features significant hydrogen bonding involving the water molecule of crystallisation that leads to the formation of a supramolecular double-layer in the bc-plane. As shown in the figure, the water molecule accepts a hydrogen bond from the amide-N—H atom [N1—H1n⋯O1w: N1—Hn = 0.844(19) Å, H1n⋯O1w = 2.107(19) Å, N1⋯O1w = 2.9464(15) Å with angle at H1n = 173.0(16)°]. This arrangement is supported by a significant fluorophenyl-C—H⋯O(water) interaction [C3—H3⋯O1w: C3—H3 = 0.951(15) Å, H3⋯O1w = 2.358(15) Å, C3⋯O1w = 3.1886(15) Å with angle at H3 = 145.7(12)°]. The water molecule also donates hydrogen bonds to the hydroxy-oxygen [O1w—H1w⋯O2i: O1w—H1w = 0.849(19) Å, H1w⋯O2i = 2.120(19) Å, O1w⋯O2i = 2.9030(13) Å with angle at H1w = 153.3(17)° for symmetry operation (i) x, 3/2 − y, 1/2 + z] and the carbonyl-oxygen atom [O1w—H2w⋯O1ii: O1w—H2w = 0.90(2) Å, H2w⋯O1ii = 1.83(2) Å, O1w⋯O1ii = 2.7115(13) Å with angle at H2w = 169(2)° for (ii) 1 − x, −1/2 + y, 3/2 − z]. The most prominent interactions between the layers along the a-axis are of the type parallel fluoride⋯π(hydroxyphenyl) [C5—F1⋯Cg(C9–C14)iii: F1⋯Cg(C9–C14)iii = 3.8932(9) Å with angle at F1 = 81.52(6)° for (iii) −1 + x, 3/2 − y, 1/2 + z].

With the aid of Crystal Explorer 17 [11] and literature precedents [12], an analysis of the calculated Hirshfeld surfaces was also conducted as well as the calculation of the full and decomposed two-dimensional fingerprint plots. For the entire asymmetric unit of (I), H⋯H contacts predominate, accounting for 40.4% of all contacts. Prominant contributions to the surface are also made by O⋯H/H⋯O [21.7%] and C⋯H/H⋯C [16.2%] contacts. Notable contacts of the type F⋯H/H⋯F [8.9%], C⋯C [5.2%] and N⋯C/C⋯N [4.7%] are also apparent but, at separations greater than the sum of the respective an der Waals radii. An analysis was also conducted on the individual components of the asymmetric unit. When the surface contacts for the Schiff base molecule alone were calculated, only very minor changes in percentage contributions were apparent. The major change were noted in a decrease in O⋯H/H⋯O [20.3%] contacts. To compensate this, the C⋯H/H⋯C [16.7%] and F⋯H/H⋯F [9.4%] surface contacts rose by 0.5%. For the water molecule, only two contacts are noted, namely O⋯H/H⋯O and H⋯H with percentage contributions of 56.8 and 42.8%, respectively.

Funding source: Sunway University Sdn Bhd

Award Identifier / Grant number: STR-RCTR-RCCM-001-2019

Funding statement: Sunway University Sdn Bhd is thanked for financial support of this work through Grant no. STR-RCTR-RCCM-001-2019.

References

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Received: 2019-08-06
Accepted: 2019-08-25
Published Online: 2019-09-09
Published in Print: 2020-02-25

©2019 Kong Mun Lo et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. Synthesis and crystal structure of bis{5-fluorine-2-(((4-(1-(methoxy-imino)ethyl)phenyl) imino)methyl)phenolato-κ2N,O}copper(II), C32H28CuF2N4O4
  3. Redetermination of the crystal structure of N′-(3-ethoxy-2-hydroxybenzylidene)-4-fluorobenzohydrazide monohydrate, C16H17FN2O4
  4. The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C15H12ClFN2O2
  5. Crystal structure of (E)-N-[4-(1H)-imidazolyl phenyl]-(2-methylphenyl)methanimine, C17H15N3
  6. The crystal structure of 1-benzyl-4-(2-(phenylethynyl)phenyl)-1H-1,2,3-triazole, C23H17N3
  7. Crystal structure of catena-poly[{μ2-1,5-bis(diphenylphosphanyl)pentane-κ2P:P′}dichloridocadmium(II)], C29H30CdCl2P2
  8. Crystal structure of methyl (E)-N2-((3-methylquinolin-8-yl)sulfonyl)-Nω′-nitro-L-argininate - ethanol (1/1), C19H28N6O7S
  9. The crystal structure of trans-carbonyl-(diphenylcyclohexyl-phosphine-κP)iodidomethyl-(2-oxopyridin-1(2H)-olato-κ2O,O′)rhodium(III), C25H28INO3PRh
  10. Crystal structure of N-(amino(pyrazin-2-yl)methylene)-6-methylpyridin-1-ium-3-carbohydrazonate-κ3O,N,N′)-(dinitrato-κ1O)zinc(II), C12H12N8O7Zn
  11. The crystal structure of dichlorido-(tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′)chromium(III) chloride — methanol (1/3), CrC27H33Cl3N7O3
  12. Crystal structure of catena-poly[aqua(μ4-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ8O,O′:O′,N:N′,O′′:O′′,O′′′))silver(I)], C10H24Ag2N2O10S2
  13. Crystal structure of bis(μ3-oxido)-bis(μ2–2,3,4,5-tetrafluorobenzoato-κ2O:O′)-bis(2,3,4,5-tetrafluorobenzoato-κO)-oktakis(3-chlorobenzyl-κC)tetratin(IV), C84H52Cl8F16O10Sn4
  14. Crystal structure of (E)-1-{4-[(4-fluoro-2-hydroxybenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15FN2O2
  15. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-N,N′)zinc(II)], {C20H30N4O4P2S4Zn}n
  16. Crystal structure of methyl 2-(4-(3-iodopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C15H12IN3O2
  17. Crystal structure of hexacarbonyl-(μ2-methanoato-k2O:O′)-(μ2–bis(di-p-tolylphosphino)cyclohexylamine-κ2P:P′)dirhenium(I), C42H45NO8P2Re2
  18. The cocrystal structure of 1′-hydroxy-1H,1′H-[5,5′-bitetrazol]-1-olate and 1,10-phenanthrolin-1-ium, C14H10N10O2
  19. The crystal structure of 1-benzyl-2-((4-(tert-butyl)phenyl)ethynyl)pyridin-1-ium bromide,C24H24BrN
  20. Crystal structure of (5,5′-bitetrazole-1,1′-diolate)-bis(1,10-phenanthroline)-copper(II), C26H16CuN12O2
  21. Crystal structure of bis(ammonium) diaqua-tetrakis(4-hydroxybenzoato)-manganese(II) tetrahydrate, [NH4]2[C28H24MnO14] ⋅ 4(H2O)
  22. The crystal structure of 3-chloro-1-hydrazino-2,4,6-trinitrobenzene, C6H4ClN5O6
  23. Crystal structure of catena-[(μ2-pyrazine-κ2N:N′)-bis(O,O′-di-ethyldithiophosphato-κ2S,S′)cadmium(II)], {C12H24CdN2O4P2S4}n
  24. Crystal structure of catena-poly[(μ2-pyrazine-N,N′)-bis(O,O′-di-isopropyldithiophosphato-S,S′)cadmium(II) acetonitrile di-solvate], [C16H32CdN2O4P2S4⋅2(C2H3N)]n
  25. Crystal structure of catena-poly{(μ2-N1,N2-bis[(pyridin-4-yl)methyl]ethanediamide-κ2N:N′)-bis(O,O′-di-isopropyldithiophosphato-κ1S)zinc(II)} — acetonitrile (1/1), C26H42N4O6P2S4Zn⋅C2H3N
  26. Crystal structure of tetraqua-bis(4-(hydroxymethyl)benzoato-κO)cobalt(II), C16H22O10Co
  27. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(4-pyridylmethylene)hydrazine-N,N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  28. Crystal structure of catena-poly[(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)-bis(O,O′-dimethyl dithiophosphato-κ2-S,S′)cadmium(II)], {C16H22CdN4O4P2S4}n
  29. Crystal structure of catena-poly[(bis(O,O′-diethyl dithiophosphato-κ2S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  30. The crystal structure of catena-poly[(E)-2-(((5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol], C12H15N3OS2Sn
  31. Crystal structure of dichlorido(N-o-tolyl-1,1-di-p-tolylphosphanamine–κ1P)-(methoxydi-p-tolylphosphane-κ1P)palladium(II), C36H39Cl2NOP2Pd
  32. The crystal structure of the triclinic polymorph of hexameric (trimethylsilyl)methyllithium, C24H66Li6Si6
  33. Crystal structure of bis(hydroxydi(pyridin-2-yl)methanolato-κ3N,N′O)cobalt(III) 7,7,8,8-tetracyanoquinodimethane, C34H22CoN8O4
  34. Synthesis and crystal structure of benzyl 5-oxo-5-phenyl-2-(quinolin-2-yl)pentanoate, C27H23NO3
  35. Crystal structure of 5,5-dimethyl-3-oxocyclohex-1-en-1-yl 4-(2,2-dichloroacetyl)-3,4-dihydro-2 H-benzo[b][1,4]oxazine-7-carboxylate, C19H19Cl2NO5
  36. Crystal structure of dipentyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C18H28O6
  37. The crystal structure of catena-poly[diaqua-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)dicadmium(II)], C30H18Cd2N2O10S2
  38. Crystal structure of 2,7-diiodo-1,3,6,8-tetramethyl-bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine, C14H14B2F4I2N4
  39. A dinuclear Eu(III) complex in the crystal structure of dodecaaqua-bis(μ2-4-(1H-tetrazol-5-yl)benzoato-κ2O:O′) bis(5-(4-carboxylatophenyl)tetrazol-1-ide) tetrahydrate, C32H50Eu2N16O24
  40. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one, C24H18F2N2O3S
  41. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-acetamidophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one-methanol-hydrate (2/1/1), C53H50F2N6O10S2
  42. Crystal structure of 4-dimethylamino-pyridin-1-ium uracil-1-acetate, C13H16N4O4
  43. Crystal structure of dimethylammonium 5-fluorouracil-1-acetate, C8H12N3O4F
  44. Crystal structure of bis(N′-((5-(ethoxycarbonyl)-1H-pyrrol-2-yl)methylene)-N-ethylcarbamohydrazonothioato-κ2N,O)nickel(II), C22H30N8O4S2Ni
  45. Crystal structure of chlorido-(η5-pentamethylcyclopentadienyl)-((bis-pyrazol-1-yl)methane-κ2N,N′) rhodium(III) hexafluorophosphate. (C17H23ClN4RhF6P)
  46. The crystal structure of 5-(benzofuran-2-carbonyl)-N-cyclohexyl-5,6-dihydrophenanthridine-6-carboxamide, C29H26N2O3
  47. The crystal structure of 2-oxo-2H-chromen-4-yl acetate, C11H8O4
  48. The crystal structure of 2-nitroisophthalic acid, C8H5NO6
  49. Crystal structure of 3-fluoro-9-methoxy-4b,5,14,15-tetrahydro-6H-isoquinolino [2′,1′:1,6]pyrazino[2,3-b]quinoxaline, C19H17FN4O
  50. Crystal structure of (4-fluorobenzyl-κC)(bis(2-hydroxyethyl) carbamodithioato-κ2S,S′)(2,2′-imino-diethanolato-κ3N,O,O′)tin(IV), C16H25FN2O4S2Sn
  51. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-bromophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18BrF3N2O3S
  52. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18ClF3N2O3S
  53. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridomanganate(II), C10H16Cl4MnN2
  54. The crystal structure of 3-carboxy-5-methylpyridin-1-ium-2-carboxylate, C8H7NO4
  55. Crystal structure of bis(3-methoxy-N-(1-(pyridin-2-yl)ethylidene)benzohydrazonato κ3O,N,N′)zinc(II), C30H28N6O4Zn
  56. Crystal structure of dichlorido-(4,4′-dichloro-2,2′-bipyridine-κ2N,N′)platinum(II) — acetone (1/1), C13H12Cl4N2PtO
  57. Crystal structure of diethyl 6,12-bis(4-fluorophenyl)-2,10-dimethoxy-3,9-diphenyl-3,9-diazatetracyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C42H42F2N2O6
  58. Synthesis and crystal structure of (1E,3E)-2-hydroxy-5-methylisophthalaldehyde O,O-di(2-((((E)-(2-hydroxynaphthalen-1-yl)methylene)amino)oxy)ethyl) dioxime, C35H32N4O7
  59. The crystal structure of 2-phenyl-4,6-bis(prop-2-yn-1-yloxy)-1,3,5-triazine, C15H11N3O2
  60. Crystal structure of 7-(2-{4-[(4-bromophenyl)methyl]piperazin-1-yl}ethoxy)-2H-chromen-2-one, C22H23BrN2O3
  61. Crystal structure of bis-[N-(3-ethyl-1-pyrazin-2-yl-ethylidene)-3-bromo-benzoic acid-hydrazonato-κ3O,N,N′)]-cadmium(II), C30H28N8O2Br2Cd
  62. Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3
  63. Crystal structure of 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid, C14H18O4
  64. The crystal structure of 3-bromo-6-methoxy-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, C13H19BBrNO3
  65. The crystal structure of 6-methyl-3,20-dioxo-19-norpregna-4,6-dien-17-yl acetate–2,4-dihydroxybenzoic acid (1/1), C30H36O8
  66. The crystal structure of (5-chloro-2-hydroxy-N-(4-methoxy-2-oxidobenzylidene)benzohydrazonato-κ3N,O,O′)-(pyridine-κ1N)copper(II), C20H16ClCuN3O4
  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
https://doi.org/10.1515/ncrs-2019-0568
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Artikel in diesem Heft

  1. Frontmatter
  2. Synthesis and crystal structure of bis{5-fluorine-2-(((4-(1-(methoxy-imino)ethyl)phenyl) imino)methyl)phenolato-κ2N,O}copper(II), C32H28CuF2N4O4
  3. Redetermination of the crystal structure of N′-(3-ethoxy-2-hydroxybenzylidene)-4-fluorobenzohydrazide monohydrate, C16H17FN2O4
  4. The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C15H12ClFN2O2
  5. Crystal structure of (E)-N-[4-(1H)-imidazolyl phenyl]-(2-methylphenyl)methanimine, C17H15N3
  6. The crystal structure of 1-benzyl-4-(2-(phenylethynyl)phenyl)-1H-1,2,3-triazole, C23H17N3
  7. Crystal structure of catena-poly[{μ2-1,5-bis(diphenylphosphanyl)pentane-κ2P:P′}dichloridocadmium(II)], C29H30CdCl2P2
  8. Crystal structure of methyl (E)-N2-((3-methylquinolin-8-yl)sulfonyl)-Nω′-nitro-L-argininate - ethanol (1/1), C19H28N6O7S
  9. The crystal structure of trans-carbonyl-(diphenylcyclohexyl-phosphine-κP)iodidomethyl-(2-oxopyridin-1(2H)-olato-κ2O,O′)rhodium(III), C25H28INO3PRh
  10. Crystal structure of N-(amino(pyrazin-2-yl)methylene)-6-methylpyridin-1-ium-3-carbohydrazonate-κ3O,N,N′)-(dinitrato-κ1O)zinc(II), C12H12N8O7Zn
  11. The crystal structure of dichlorido-(tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′)chromium(III) chloride — methanol (1/3), CrC27H33Cl3N7O3
  12. Crystal structure of catena-poly[aqua(μ4-piperazine-1,4-bis(2-hydroxypropanesulfonato-κ8O,O′:O′,N:N′,O′′:O′′,O′′′))silver(I)], C10H24Ag2N2O10S2
  13. Crystal structure of bis(μ3-oxido)-bis(μ2–2,3,4,5-tetrafluorobenzoato-κ2O:O′)-bis(2,3,4,5-tetrafluorobenzoato-κO)-oktakis(3-chlorobenzyl-κC)tetratin(IV), C84H52Cl8F16O10Sn4
  14. Crystal structure of (E)-1-{4-[(4-fluoro-2-hydroxybenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15FN2O2
  15. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-N,N′)zinc(II)], {C20H30N4O4P2S4Zn}n
  16. Crystal structure of methyl 2-(4-(3-iodopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C15H12IN3O2
  17. Crystal structure of hexacarbonyl-(μ2-methanoato-k2O:O′)-(μ2–bis(di-p-tolylphosphino)cyclohexylamine-κ2P:P′)dirhenium(I), C42H45NO8P2Re2
  18. The cocrystal structure of 1′-hydroxy-1H,1′H-[5,5′-bitetrazol]-1-olate and 1,10-phenanthrolin-1-ium, C14H10N10O2
  19. The crystal structure of 1-benzyl-2-((4-(tert-butyl)phenyl)ethynyl)pyridin-1-ium bromide,C24H24BrN
  20. Crystal structure of (5,5′-bitetrazole-1,1′-diolate)-bis(1,10-phenanthroline)-copper(II), C26H16CuN12O2
  21. Crystal structure of bis(ammonium) diaqua-tetrakis(4-hydroxybenzoato)-manganese(II) tetrahydrate, [NH4]2[C28H24MnO14] ⋅ 4(H2O)
  22. The crystal structure of 3-chloro-1-hydrazino-2,4,6-trinitrobenzene, C6H4ClN5O6
  23. Crystal structure of catena-[(μ2-pyrazine-κ2N:N′)-bis(O,O′-di-ethyldithiophosphato-κ2S,S′)cadmium(II)], {C12H24CdN2O4P2S4}n
  24. Crystal structure of catena-poly[(μ2-pyrazine-N,N′)-bis(O,O′-di-isopropyldithiophosphato-S,S′)cadmium(II) acetonitrile di-solvate], [C16H32CdN2O4P2S4⋅2(C2H3N)]n
  25. Crystal structure of catena-poly{(μ2-N1,N2-bis[(pyridin-4-yl)methyl]ethanediamide-κ2N:N′)-bis(O,O′-di-isopropyldithiophosphato-κ1S)zinc(II)} — acetonitrile (1/1), C26H42N4O6P2S4Zn⋅C2H3N
  26. Crystal structure of tetraqua-bis(4-(hydroxymethyl)benzoato-κO)cobalt(II), C16H22O10Co
  27. Crystal structure of catena-[(bis(O,O′-diethyl dithiophosphato-S,S′)-μ2-1,2-bis(4-pyridylmethylene)hydrazine-N,N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  28. Crystal structure of catena-poly[(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)-bis(O,O′-dimethyl dithiophosphato-κ2-S,S′)cadmium(II)], {C16H22CdN4O4P2S4}n
  29. Crystal structure of catena-poly[(bis(O,O′-diethyl dithiophosphato-κ2S,S′)-μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N:N′)cadmium(II)], {C20H30CdN4O4P2S4}n
  30. The crystal structure of catena-poly[(E)-2-(((5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol], C12H15N3OS2Sn
  31. Crystal structure of dichlorido(N-o-tolyl-1,1-di-p-tolylphosphanamine–κ1P)-(methoxydi-p-tolylphosphane-κ1P)palladium(II), C36H39Cl2NOP2Pd
  32. The crystal structure of the triclinic polymorph of hexameric (trimethylsilyl)methyllithium, C24H66Li6Si6
  33. Crystal structure of bis(hydroxydi(pyridin-2-yl)methanolato-κ3N,N′O)cobalt(III) 7,7,8,8-tetracyanoquinodimethane, C34H22CoN8O4
  34. Synthesis and crystal structure of benzyl 5-oxo-5-phenyl-2-(quinolin-2-yl)pentanoate, C27H23NO3
  35. Crystal structure of 5,5-dimethyl-3-oxocyclohex-1-en-1-yl 4-(2,2-dichloroacetyl)-3,4-dihydro-2 H-benzo[b][1,4]oxazine-7-carboxylate, C19H19Cl2NO5
  36. Crystal structure of dipentyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C18H28O6
  37. The crystal structure of catena-poly[diaqua-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)-(μ4-5-(benzo[d]thiazol-2-yl)benzene-1,3-dicarboxylate-κ4O,O′:O′′,O′′′)dicadmium(II)], C30H18Cd2N2O10S2
  38. Crystal structure of 2,7-diiodo-1,3,6,8-tetramethyl-bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine, C14H14B2F4I2N4
  39. A dinuclear Eu(III) complex in the crystal structure of dodecaaqua-bis(μ2-4-(1H-tetrazol-5-yl)benzoato-κ2O:O′) bis(5-(4-carboxylatophenyl)tetrazol-1-ide) tetrahydrate, C32H50Eu2N16O24
  40. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one, C24H18F2N2O3S
  41. Crystal structure and anti-inflammatory activity of (3E,5E)-3-(2-fluorobenzylidene)-1-((4-acetamidophenyl)sulfonyl)-5-(pyridin-3-ylmethylene)piperidin-4-one-methanol-hydrate (2/1/1), C53H50F2N6O10S2
  42. Crystal structure of 4-dimethylamino-pyridin-1-ium uracil-1-acetate, C13H16N4O4
  43. Crystal structure of dimethylammonium 5-fluorouracil-1-acetate, C8H12N3O4F
  44. Crystal structure of bis(N′-((5-(ethoxycarbonyl)-1H-pyrrol-2-yl)methylene)-N-ethylcarbamohydrazonothioato-κ2N,O)nickel(II), C22H30N8O4S2Ni
  45. Crystal structure of chlorido-(η5-pentamethylcyclopentadienyl)-((bis-pyrazol-1-yl)methane-κ2N,N′) rhodium(III) hexafluorophosphate. (C17H23ClN4RhF6P)
  46. The crystal structure of 5-(benzofuran-2-carbonyl)-N-cyclohexyl-5,6-dihydrophenanthridine-6-carboxamide, C29H26N2O3
  47. The crystal structure of 2-oxo-2H-chromen-4-yl acetate, C11H8O4
  48. The crystal structure of 2-nitroisophthalic acid, C8H5NO6
  49. Crystal structure of 3-fluoro-9-methoxy-4b,5,14,15-tetrahydro-6H-isoquinolino [2′,1′:1,6]pyrazino[2,3-b]quinoxaline, C19H17FN4O
  50. Crystal structure of (4-fluorobenzyl-κC)(bis(2-hydroxyethyl) carbamodithioato-κ2S,S′)(2,2′-imino-diethanolato-κ3N,O,O′)tin(IV), C16H25FN2O4S2Sn
  51. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-bromophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18BrF3N2O3S
  52. Crystal structure and anti-inflammatory activity of (3E,5E)-1-((4-chlorophenyl)sulfonyl)-3-(pyridin-4-ylmethylene)-5-(2-(trifluoromethyl)benzylidene)piperidin-4-one, C25H18ClF3N2O3S
  53. The crystal structure of 3-((1R,2S)-1-methylpyrrolidin-1-ium-2-yl)pyridin-1-ium tetrachloridomanganate(II), C10H16Cl4MnN2
  54. The crystal structure of 3-carboxy-5-methylpyridin-1-ium-2-carboxylate, C8H7NO4
  55. Crystal structure of bis(3-methoxy-N-(1-(pyridin-2-yl)ethylidene)benzohydrazonato κ3O,N,N′)zinc(II), C30H28N6O4Zn
  56. Crystal structure of dichlorido-(4,4′-dichloro-2,2′-bipyridine-κ2N,N′)platinum(II) — acetone (1/1), C13H12Cl4N2PtO
  57. Crystal structure of diethyl 6,12-bis(4-fluorophenyl)-2,10-dimethoxy-3,9-diphenyl-3,9-diazatetracyclo[6.4.0.02,7.04,11]dodecane-1,5-dicarboxylate, C42H42F2N2O6
  58. Synthesis and crystal structure of (1E,3E)-2-hydroxy-5-methylisophthalaldehyde O,O-di(2-((((E)-(2-hydroxynaphthalen-1-yl)methylene)amino)oxy)ethyl) dioxime, C35H32N4O7
  59. The crystal structure of 2-phenyl-4,6-bis(prop-2-yn-1-yloxy)-1,3,5-triazine, C15H11N3O2
  60. Crystal structure of 7-(2-{4-[(4-bromophenyl)methyl]piperazin-1-yl}ethoxy)-2H-chromen-2-one, C22H23BrN2O3
  61. Crystal structure of bis-[N-(3-ethyl-1-pyrazin-2-yl-ethylidene)-3-bromo-benzoic acid-hydrazonato-κ3O,N,N′)]-cadmium(II), C30H28N8O2Br2Cd
  62. Crystal structure of 6-(4-fluorophenyl)-4-methoxy-2H-pyran-2-one, C12H9FO3
  63. Crystal structure of 3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid, C14H18O4
  64. The crystal structure of 3-bromo-6-methoxy-2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, C13H19BBrNO3
  65. The crystal structure of 6-methyl-3,20-dioxo-19-norpregna-4,6-dien-17-yl acetate–2,4-dihydroxybenzoic acid (1/1), C30H36O8
  66. The crystal structure of (5-chloro-2-hydroxy-N-(4-methoxy-2-oxidobenzylidene)benzohydrazonato-κ3N,O,O′)-(pyridine-κ1N)copper(II), C20H16ClCuN3O4
  67. Crystal structure of (E)-2-cyano-N′-(1-(3-ethylpyrazin-2-yl)ethylidene)acetohydrazide, C11H3N5O
  68. Crystal structure of (2,7-dihexyl-9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane), C51H56OP2
  69. Crystal structure of 5-((bis(pyridin-2-ylmethyl)amino)methyl)quinolin-8-ol, C22H20N4O
  70. Crystal structure of 3-(2-(5-(4-fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one, C28H20FN3O2S
  71. The crystal structure of [(tetra-μ2-2,6-difluorobenzoato-κ2O:O′)-bis-(2,6-difluorobenzoato-κ2O:O′)-bis-(1,10-phenanthroline-κ2N:N′)]dierbium(III) C66H34N4O12F12Er2
  72. Crystal structure of bis(3-chloro-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-k3N,N′,O)nickel(II), C26H20N8O2Cl2Ni
  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
  74. Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
  76. Crystal structure of 6-iodo-3-phenyl-2-propylquinazolin-4(3H)-one, C17H15IN2O
  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
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