Home Physical Sciences Crystal structure of (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)methanimine, C12H9ClN2
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Crystal structure of (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)methanimine, C12H9ClN2

  • Nyameka Diko , Sizwe J. Zamisa ORCID logo EMAIL logo , Holger B. Friedrich and Mzamo L. Shozi
Published/Copyright: August 2, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 5

Abstract

C12H9ClN2, monoclinic, P21/c (no. 14), a = 19.0184(3) Å, b = 4.81220(10) Å, c = 11.3896(2) Å, β = 107.388(1)°, Z = 4, V = 994.75(3) Å3, Rgt(F) = 0.0284, wRref(F2) = 0.0800, T = 100(2) K.

CCDC no.: 1940898

The molecular structure is 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:Colourless rod
Size:0.33 × 0.28 × 0.16 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.35 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:28.3°, >99%
N(hkl)measured, N(hkl)unique, Rint:12228, 2467, 0.023
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2212
N(param)refined:136
Programs:Bruker [1], SHELX [2], [3], Mercury [4]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.45707(2)1.41456(6)0.64710(2)0.01753(9)
N10.12186(6)0.0816(2)0.34983(9)0.0182(2)
N20.25339(5)0.5930(2)0.33224(9)0.0161(2)
C10.07401(7)−0.1009(3)0.28098(12)0.0191(2)
H10.045648−0.2095220.3198270.023*
C20.06330(7)−0.1414(3)0.15626(11)0.0203(2)
H20.029215−0.2758540.1113790.024*
C30.10384(7)0.0204(3)0.09888(12)0.0231(3)
H30.0974280.0004640.0133320.028*
C40.15370(7)0.2111(3)0.16800(11)0.0199(2)
H40.1819780.3244410.1307810.024*
C50.16162(6)0.2337(2)0.29328(10)0.0152(2)
C60.21388(6)0.4290(2)0.37348(10)0.0159(2)
H60.2182710.4328160.4587730.019*
C70.30101(6)0.7830(2)0.41370(10)0.0146(2)
C80.29410(6)0.8655(3)0.52796(10)0.0163(2)
H80.2562550.7880170.5564940.020*
C90.34210(6)1.0592(2)0.59942(10)0.0160(2)
H90.3371831.1153640.6765470.019*
C100.39743(6)1.1704(2)0.55726(10)0.0144(2)
C110.40509(6)1.0939(2)0.44428(11)0.0165(2)
H110.4430381.1720190.4161940.020*
C120.35647(6)0.9017(2)0.37308(10)0.0163(2)
H120.3609990.8498840.2951890.020*

Source of material

An ethanoic solution of 2-pyridinecarboxaldehye (1.70 g, 10 mmol) was added to a solution of 4-chloroaniline (1.28 g, 10 mmol) in ethanol and the solution was refluxed for 6 h at a temperature of 100 °C. MgSO4 was added once the mixture was cooled to remove excess water, under reduced pressure and the product was dried under vacuum overnight. This gave an off-white powder (1.70 g, 79%) Mp: 68.9–69.4 °C. Crystals were grown through a slow evaporation of an ethanoic solution at 25 °C. 1H NMR (400 MHz, DMSO, δ, ppm) δH = 8.72 (d, 1H, J = 4.68 Hz), 8.58 (s, 1H), 8.15 (d, 1H, J = 7.72 Hz), 7.95 (td, 1H, J = 1.50, 7.96, 15.47 Hz), 7.53 (dd, 1H, J = 4.99, 12.09 Hz), 7.48 (d, 2H, J = 8.57 Hz), 7.36 (δ, 2H, d, J = 8.49 Hz). 13C NMR (400 MHz, DMSO, δ, ppm): 161.5, 153.8, 149.6, 149.2, 137.0, 131.0, 129.2, 125.8, 122.9, 121.3. IR(ATR)/cm−1: 3051 (ar C—H), 1622 (C=N).

Experimental details

The structure was solved by the direct method using the SHELXS [2] program and refined. The visual crystal structure information was performed using Mercury [4] system software. All hydrogen atoms were placed in idealized positions and refined in riding models with Uiso assigned the values of 1.2 times those of their parent atoms and the distances of C—H were constrained to 0.95 Å for all the aromatic H atoms.

Comment

Pyridyl imine ligands are N,N-bidentate ligands that are formed via a condensation reaction between an aldehyde and imines. These ligands have popularity amongst chemists for their ease of synthesis, the ability to accommodate metals in various oxidation states and versatility to perform various applications [5], [6], [7]. These ligands with modifications have been coordinated to various transition metals for various catalytic reactions such as: polymerization and Heck reactions when coordinated to Pd [6], [8] and olefin epoxidation when coordinated to Re [9]. Our interests in N,N-bidentate ligands includes application of new complexes in biological [10] as well as catalytic studies [11].

The crystal structure of the title compound contains one molecule in the asymmetric unit with an E conformation around the N2=C6 bond. The pyridyl and phenyl rings are not co-planar, but rather have a dihedral angle of 17.3°. All bond angles and distances are comparable to those of closely related compounds in literature [12], [13], [14], [15], [16], [17]. Intermolecular C10—Cl1⋯Cgphenyi interactions were observed in the crystal packing with Cl⋯Cgphenyli distance of 3.56 Å and C10—Cl1⋯Cgphenyli angle of 92.21(4)° (symmetry code: (i) = x, 1 + y, z). Furthermore, Cl1⋯Cl1ii,iii halogen bonding patterns (symmetry codes: (ii) = 1 − x, 1/2 + y, 3/2 − z; (iii) = 1 − x, −1/2 + y, 3/2 − z) were also observed in the crystal packing and together with the C10—Cl1⋯Cgphenyl interactions, form one dimensional supramolecular architectures which extend along the b axis.

Acknowledgements

We would like to thank the DST- National Research Foundation Centre of Excellence in Catalysis C* change for financial support.

References

1. Bruker. APEXII. Bruker AXS Inc, Madison, WI, USA (2009).Search in Google Scholar

2. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

4. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A.: Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures. J. Appl. Crystallogr. 41 (2008) 466–470.10.1107/S0021889807067908Search in Google Scholar

5. Mondal, J.; Ghorai, A.; Singh, S. K.; Saha, R.; Patra, G. K.: Synthesis, structure, photophysical and catalytic properties of CuI–iodide complexes of di-imine ligands. J. Mol. Struct. 1108 (2016) 315–324.10.1016/j.molstruc.2015.12.028Search in Google Scholar

6. Park, S.; Lee, J.; Jeong, J. H.; Lee, H.; Nayab, S.: Palladium(II) complexes containing N,N′-bidentate imine ligands derived from picolinaldehyde and substituted anilines: synthesis, structure and polymerisation of methyl methacrylate. Polyhedron 151 (2018) 82–89.10.1016/j.poly.2018.05.031Search in Google Scholar

7. Aboura, W.; Benabdallah, T.; Zhang, F.; Therrien, B.: Alkoxylation of the imine carbon atom of a Schiff-base ligand upon coordination to arene ruthenium. Inorg. Chim. Acta 483 (2018) 93–97.10.1016/j.ica.2018.07.025Search in Google Scholar

8. Elantabli, F. M.; Radebe, M. P.; Motswainyana, W. M.; Owaga, B. O.; El-Medani, S. M.; Ekengard, E.; Haukka, M.; Nordlander, E.; Onani, M. O.: Thiophene based imino-pyridyl palladium(II) complexes: synthesis, molecular structures and Heck coupling reactions. J. Organomet. Chem. 843 (2017) 40–47.10.1016/j.jorganchem.2017.04.022Search in Google Scholar

9. Song, X.; Lim, M. H.; Mohamed, D. K. B.; Wong, S. M.; Zhao, J.; Hor, T. S. A.: Re(I) carbonyl complexes containing pyridyl-imine and amine ligands: synthesis, characterization and their catalytic olefin epoxidation activities. J. Organomet. Chem. 814 (2016) 1–7.10.1016/j.jorganchem.2016.04.010Search in Google Scholar

10. Thangavel, S.; Paulpandi, M.; Friedrich, H. B.; Murugan, K.; Kalva, S.; Skelton, A. A.: Synthesis, characterization, antiproliferative and molecular docking study of new half sandwich Ir(III), Rh(III) and Ru(II) complexes. J. Inorg. Biochem. 159 (2016) 50–61.10.1016/j.jinorgbio.2016.02.006Search in Google Scholar PubMed

11. Gichumbi, J.; Friedrich, H.; Omondi, B.: Synthesis and characterization of half-sandwich ruthenium(II) complexes with N-alkyl pyridyl-imine ligands and their application in transfer hydrogenation of ketones. Transition Met. Chem. 41 (2016) 867–877.10.1007/s11243-016-0089-5Search in Google Scholar

12. Saphu, W.; Chainok, K.: Crystal structure of 4-nitro-N-[(pyridin-2-yl)methylidene]aniline. Acta Crystallogr. E71 (2015) o760.10.1107/S2056989015016928Search in Google Scholar PubMed PubMed Central

13. Marjani, K.; Mousavi, M.; Namazian, F.: Crystal structure of N-(2-pyridylmethylene)benzene-1,4-diamine. J. Chem. Crystallogr. 41 (2011) 1451–1455.10.1007/s10870-011-0120-9Search in Google Scholar

14. Zheng, Z. N.; Lee, S. W.: (E)-2-{4-[(Pyridin-2-yl)methylideneamino]phenyl}acetic acid. Acta Crystallogr. E68 o774.10.1107/S1600536812006472Search in Google Scholar PubMed PubMed Central

15. Biewer, C.; Hamacher, C.; Kaiser, A.; Vogt, N.; Sandleben, A.; Chin, M. T.; Yu, S.; Vicic, D. A.; Klein, A.: Unsymmetrical N-aryl-1-(pyridin-2-yl)methanimine ligands in organonickel(II) complexes: more than a blend of 2,2′-bipyridine and N,N-diaryl-a-diimines. Inorg. Chem. 55 (2016) 12716–12727.10.1021/acs.inorgchem.6b01874Search in Google Scholar PubMed

16. Tzimopoulos, D.; Czapik, A.; Gdaniec, M.; Bakas, T.; Isab, A. A.; Varvogli, A.-C.; Akrivos, P. D.: Synthesis and study of triorganostannyl esters of 3,4- and 3,5-pyridinylimino substituted aminobenzoic acids: crystal structures of dimorphs of aqua-trimethyltin 3-pyridinyliminobenzoate. J. Mol. Struct. 965 (2010) 56–64.10.1016/j.molstruc.2009.11.038Search in Google Scholar

17. Dong, Y.-W.; Fan, R.-Q.; Wang, X.-M.; Wang, P.; Zhang, H.-J.; Wei, L.-G.; Song, Y.; Du, X.; Chen, W.; Yang, Y.-L.: Topological evolution in mercury(II) Schiff base complexes tuned through alkyl substitution – synthesis, solid-state structures, and aggregation-induced emission properties. Eur. J. Inorg. Chem. 2016 (2016) 3598–3610.10.1002/ejic.201600231Search in Google Scholar

Received: 2019-04-09
Accepted: 2019-07-16
Published Online: 2019-08-02
Published in Print: 2019-09-25

©2019 Nyameka Diko et al., published by De Gruyter, Berlin/Boston

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

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  74. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-methyl-1H-imidazol-3-ium hexafluoridophosphate(V), C8H13F6N2O2P
  75. Crystal structure of bis[(2-(2-bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κO)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) hemihydrate C42H65Br2N4NiO8.5
  76. The crystal structure of N-(7-(4-fluorobenzylidene)-3-(4-fluorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbonothioyl)benzamide, C28H23F2N3OS
  77. The crystal structure of N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide, C18H20N4O2
  78. Crystal structure of (E)-2-(3,6-bis(ethylamino)-2,7-dimethyl-9H-xanthen-9-yl)-N′-((6-methylpyridin-2-yl)methylene)benzohydrazide – methanol (1/1), C34H37N5O3
  79. Crystal structure of 2-oxo-1-(pyrimidin-5-ylmethyl)-3-(3-(trifluoromethyl)phenyl)-1,2-dihydro-5l4-pyrido[1,2-a]pyrimidin-4-olate, C20H13F3N4O2
  80. Crystal structure of poly[(μ3-9H-carbazole-3,6-dicarboxylato-κ3O1: O2: O3)(μ2-4-(pyridin-4-yl)pyridine-κ2N1:N1′)zinc(II)], C19H11N2O4Zn
  81. Crystal structure of (E)-N′-((1,8-dihydropyren-1-yl)-methylene)picolinohydrazide, C23H15N3O
  82. Crystal structure of catena-poly{[μ2-1,2-bis(diphenylphosphino)ethane]dichloridocadmium(II)}, C26H24CdCl2P2
  83. Crystal structure of the 1:2 co-crystal between N,N′-bis(4-pyridylmethyl)oxalamide and acetic acid as a dihydrate, C14H14N4O2⋅2 C2H4O2⋅2 H2O
  84. Crystal structure of the co-crystal N,N′-bis(3-pyridylmethyl)oxalamide acetic acid (1/2), C14H14N4O2⋅2C2H4O2
  85. Crystal structure of the co-crystal N,N′-bis(4-pyridylmethyl)oxalamide and 2,3,5,6-tetrafluoro-1,4-di-iodobenzene (1/1), C14H14N4O2⋅C6F4I2
  86. Crystal structure of the co-crystal 4-[(4-carboxyphenyl)disulfanyl]benzoic acid–(1E,4E)-1-N,4-N-bis(pyridin-4-ylmethylidene)cyclohexane-1,4-diamine (1/1), C14H10O4S2⋅C18H20N4
  87. Crystal structure of hexacarbonyl-bis(μ2-di-n-propyldithiocarbamato-κ3S,S′:S;κ3S:S:S′)-di-rhenium(I), C20H28N2O6Re2S4
  88. Crystal structure of fac-tricarbonyl-morpholine-κN-(morpholinocarbamodithioato-κ2S,S′)rhenium(I), C12H17N2O5ReS2
https://doi.org/10.1515/ncrs-2019-0260
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of poly[diaqua-(μ8-1,1′:2′,1′′-terphenyl-3,3′′,4′,5′-tetracarboxylato-κ8O1:O2:O3:O4:O5:O6:O7:O8)dicopper(II)], C22H14Cu2O10
  3. Crystal structure of 2-((1H-benzo[d]imidazol-2-ylimino)methyl)-4,6-di-tert-butylphenol, C22H27N3O
  4. Crystal structure of (4-ethoxynaphthalen-1-yl)(furan-2-yl)methanone, C17H14O3
  5. Crystal structure of 1-nonylpyridazin-1-ium iodide, C13H23N2I
  6. Crystal structure of bis[diaqua(1,10-phenanthroline-κ2N, N′)-copper(II)]diphenylphosphopentamolybdate dihydrate, C36H38Cu2Mo5N4O27P2
  7. The crystal structure of tetrakis(imidazole)-copper(I) hexafluorophosphate, C12H16CuF6PN8
  8. The crystal structure of dimethyl ((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)phosphonate, C23H33O4P
  9. Crystal structure of diaqua-bis(1,10-phenanthroline κ2N,N′)nickel(II) trifluoroacetate- trifluoroacetic acid (1/1), C30H21F9N4NiO8
  10. Crystal structure of 2-(naphthalen-2-yl)-1,8-naphthyridine, C18H12N2
  11. Synthesis and crystal structure of a new polymorph of diisopropylammonium trichloroacetate, C8H16Cl3NO2
  12. Crystal structure of dimethanol-bis(1-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN)-bis(thiocyanato-κN)cadmium(II) C34H34CdN12O2S2
  13. Crystal structure of ethyl 2,2-difluoro-2-(7-methoxy-2-oxo-2H-chromen-3-yl)acetate, C14H12F2O5
  14. The crystal structure of bis[μ2-(N,N-diethylcarbamodithioato-κS:κS,κS′)] bis[1′-(diphenylphosphino-κP)-1-cyanoferrocene]disilver(I), C56H56Ag2Fe2N4P2S4
  15. Crystal structure of bis(di-n-butylammonium) tetrachloridodiphenylstannate(IV), C28H50Cl4N2Sn
  16. The crystal structure of poly[(μ5-2-((5-bromo-3-formyl-2-hydroxybenzylidene)amino)benzenesulfonato-κ6O:O:O,O′:O′:O′′)sodium(I)], C13H9O4NSBrNa
  17. Crystal structure of catena-{poly[bis(O,O′-diethyldithiophosphato-S)-(μ2-1,2-bis(4-pyridylmethylene)hydrazine-N,N′)-zinc(II)] di-acetonitrile solvate}, {C20H30N4O4P2S4Zn ⋅ 2 C2H3N}n
  18. Halogen and hydrogen bonding in the layered crystal structure of 2-iodoanilinium triiodide, C6H7I4N
  19. Crystal structure of cyclohexane-1,4-diammonium 2-[(2-carboxylatophenyl)disulfanyl]benzoate — dimethylformamide — monohydrate (1/1/1), [C6H16N2][C14H8O4S2] ⋅ C3H7NO⋅H2O
  20. The synthesis and crystal structure of isobutyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C16H13Cl2F6N3O3S
  21. Isolation and crystal structure of bufotalinin — methanol (1/1), C25H34O7
  22. Crystal structure of benzylbis(1,3-diphenylpropane-1,3-dionato-κ2O,O′) chloridotin(IV), C37H29ClO4Sn
  23. Crystal structure of Bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-methyl-imidazol)}diiodidocadmium(II), [Cd(C11H11N5)2I2], C22H22N10I2Cd
  24. Crystal structure of 4-isobutoxybenzaldehyde oxime, C11H15NO2
  25. The crystal structure of bis(acetato-κ1O)-bis(N′-hydroxypyrimidine-2-carboximidamide-κ2N,N′)manganese(II) — methanol (1/2), C14H18MnN8O6, 2(CH3OH)′
  26. Crystal structure of poly[bis(μ2-bis(4-(1H-imidazol-1-yl)phenyl)amine-κ2N:N′)-bis(nitrato-κO)cadmium(II)], C36H30CdN12O6
  27. Crystal structure and optical properties of 1,6-bis(methylthio)pyrene, C18H14S2
  28. The crystal structure of hexaquamagnesium(II) bis(3,4-dinitropyrazol-1-ide), C6H14MgN8O14
  29. Halogen bonds in the crystal structure of 4,3:5,4-terpyridine – 1,4-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  30. Crystal structure and photochromic properties of a novel photochromic perfluordiarylethene containing a triazole bridged pyridine group moiety, C24H18F6N4S2
  31. Crystal structure of bis[(μ3-oxido)-(μ2-(N,N-diisopropylthiocarbamoylthio) acetato-κ2O,O′)-((N,N-diisopropylthiocarbamoylthio)acetato-κO)-bis(di-4-methylbenzyl-tin(IV))], C100H136N4O10S8Sn4
  32. Crystal structure of dibromidobis(4-bromobenzyl)tin(IV), C14H12Br4Sn
  33. The crystal structure of (4Z)-2-[(E)-(1-ethyl-3,3-dimethyl-1,3-dihydro-2H-indol-2-ylidene)methyl]-4-[(1-ethyl-3,3-dimethyl-3H-indolium-2-yl)methylidene]-3-oxocyclobut-1-en-1-olate, C30H32N2O2
  34. The crystal structure of (E)-3-(4-(dimethylamino)styryl)-5,5-dimethylcyclohex-2-en-1-one, C18H23NO
  35. Crystal structure of dihydrazinium 1H-pyrazole-3,5-dicarboxylate, C5H12N6O4
  36. Crystal structure of poly[μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)-(μ2-4-sulfidobenzoate-κ2O:S)cobalt(II)] dihydrate, C42H44Co2N8O7S2
  37. Crystal structure of 8-(3,4-dimethylbenzylidene)-6,10-dioxaspiro[4.5]decane-7,9-dione, C17H18O4
  38. Crystal structure of 4-(2-bromo-4-(6-morpholino-3-phenyl-3H-benzo[f]chromen-3-yl) cyclohexa-2,5-dien-1-yl)morpholine, C33H31BrN2O
  39. Synthesis and crystal structure of 2-((1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)methylene)-2,3-dihydro-1H-inden-1-one, C23H16N2OS
  40. Crystal structure of poly[(μ2-1,1′-(oxybis(4,1-phenylene)bis(1H-imidazole)-κ2N,N′)(μ2-1,3-benzenecarboxylato-κ3O,O′:O′′)zinc(II)] dihydrate, C26H22N4O7Zn
  41. Crystal structure of diaqua-bis(cinnamato-κ2O,O′)zinc(II), C18H18ZnO6
  42. Crystal structure of 2-(prop-2-yn-1-yloxy)-1-naphthaldehyde, C14H10O2
  43. Crystal structure and photochromic properties of 1-(2-methyl-5-phenyl-3-thienyl)-2-{2-methyl-5-[4-(9-fluorenone hydrazone)-phenyl]-3-thienyl}perfluorocyclopentene, C41H26F6N2S2
  44. Hydrothermal synthesis and crystal structure of cylo[tetraaqua-bis(μ2-1,4-bis(1H-benzo[d]imidazol-1-yl)but-2-ene-κ2N:N′)-bis(μ2-4-nitro-phthalate-κ2O,O′)dinickel(II)], C26H23N5O8Ni
  45. Crystal structure of 3-[methyl(phenyl)amino]-1-phenylthiourea, C14H15N3S
  46. Crystal structure of 1-(4-chlorophenyl)-3-[methyl(phenyl)amino]thiourea, C14H14ClN3S
  47. Crystal structure of 2-tert-butyl-1H-imidazo[4,5-b]pyridine, C10H13N3
  48. Crystal structure of 5-carboxy-2-(2-carboxyphenyl)-1H-imidazol-3-ium-4-carboxylate dihydrate, C12H8N2O6⋅2(H2O)
  49. The crystal structure of dichlorido-μ2-dichlorido-(η2-1,4-bis(4-vinylbenzyl)-1,4-diazabicyclo[2.2.2]octane-1,4-diium)dicopper(I), C24H30N2Cu2Cl4
  50. Crystal structure of 4-bromobenzyl (Z)-N-(adamantan-1-yl)morpholine-4-carbothioimidate, C22H29BrN2OS
  51. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene-1(6bH)-one, C30H48O2
  52. Crystal structure of 3,5-bis(trifluoromethyl)benzyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidate, C30H33F6N3S
  53. The crystal structure of 3-methoxyphenanthridin-6(5H)-one, C14H11NO2
  54. Crystal structure of 4-(5,5-difluoro-1,3,7,9-tetramethyl-3H,5H-5λ4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-10-yl)pyridin-1-ium tetraiodidoferrate(III), C18H19BF2FeI4N3
  55. Crystal structure of 2-(3-methoxyphenyl)-3-((phenylsulfonyl)methyl)imidazo[1,2-a]pyridine, C21H18N2O3S
  56. Crystal structure of [(2-(2-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, C29H50Cl2N4NiO8
  57. Crystal structure of (Z)-6-(dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)-2-(2-(quinoxalin-2-ylmethylene)hydrazinyl)-2,3-dihydroinden-1-one, C35H35N7O
  58. 5-Methyl-N′-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl]-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbohydrazide, C22H22N8O2
  59. Crystal structure of 2,3-dichloro-6-methoxyquinoxaline, C9H6Cl2N2O
  60. Synthesis and crystal structure of 7-chloro-2-(ethylsulfinyl)-6-fluoro-3-(1H-pyrazole-1-yl)-4H-thiochromen-4-one, C13H10FN3OS2
  61. Crystal structure of 4-ethylpiperazine-1-carbothioic dithioperoxyanhydride, C14H26N4S4
  62. Crystal structure of 2-(2-(6-methylpyridin-2-yl)naphthalen-1-yl)pyrimidine, C20H15N3
  63. The crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-3-methylbenzohydrazide, C23H22N2O4
  64. Crystal structure of catena-poly[(μ2-isophthalato-κ2O:O′)-(2,5-di(pyrazin-2-yl)-4,4′-bipyridine-κ3N,N′,N′′)zinc(II)] — water (2/5), C26H21N6O6.5Zn
  65. Crystal structure of (3E,5E)-3,5-bis(3-nitrobenzylidene)-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperidin-4-one — dichloromethane (2/1), C53H38Cl2F6N6O14S2
  66. Crystal structure of (μ2-oxido)-bis(N,N′-o-phenylenebis(salicylideneiminato))diiron(III) — N,N′-dimethylformamide, C47H43Fe2N4O9
  67. Crystal structure of N1,N3-bis(2-hydroxyethyl)-N1, N1,N3,N3-tetramethylpropane-1,3-diaminium dibromide, C11H28Br2N2O2
  68. Crystal structure of (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)methanimine, C12H9ClN2
  69. Crystal structure of 8-bromo-6-oxo-2-phenyl-6H-pyrrolo[3,2,1-ij]quinoline-5-carbaldehyde, C18H11BrNO2
  70. Crystal structure of 1,4-bis(2-azidoethyl)piperazine-1,4-diium dichloride trihydrate, C8H18N8Cl2 ⋅ 3 H2O
  71. Crystal structure of (E)-4-bromo-N-(pyridin-2-ylmethylene)aniline, C12H9BrN2
  72. Crystal structure of bis[(2-(3-bromophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ-O)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Br2N4NiO8
  73. The crystal structure of (1E,2E)-2-methyl-4-((7-oxo-7H-furo[3,2-g]chromen-9-yl)oxy)but-2-enal O-isonicotinoyl oxime–trichloromethane (3/1), C67H49Cl3N6O18
  74. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-methyl-1H-imidazol-3-ium hexafluoridophosphate(V), C8H13F6N2O2P
  75. Crystal structure of bis[(2-(2-bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κO)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) hemihydrate C42H65Br2N4NiO8.5
  76. The crystal structure of N-(7-(4-fluorobenzylidene)-3-(4-fluorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbonothioyl)benzamide, C28H23F2N3OS
  77. The crystal structure of N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide, C18H20N4O2
  78. Crystal structure of (E)-2-(3,6-bis(ethylamino)-2,7-dimethyl-9H-xanthen-9-yl)-N′-((6-methylpyridin-2-yl)methylene)benzohydrazide – methanol (1/1), C34H37N5O3
  79. Crystal structure of 2-oxo-1-(pyrimidin-5-ylmethyl)-3-(3-(trifluoromethyl)phenyl)-1,2-dihydro-5l4-pyrido[1,2-a]pyrimidin-4-olate, C20H13F3N4O2
  80. Crystal structure of poly[(μ3-9H-carbazole-3,6-dicarboxylato-κ3O1: O2: O3)(μ2-4-(pyridin-4-yl)pyridine-κ2N1:N1′)zinc(II)], C19H11N2O4Zn
  81. Crystal structure of (E)-N′-((1,8-dihydropyren-1-yl)-methylene)picolinohydrazide, C23H15N3O
  82. Crystal structure of catena-poly{[μ2-1,2-bis(diphenylphosphino)ethane]dichloridocadmium(II)}, C26H24CdCl2P2
  83. Crystal structure of the 1:2 co-crystal between N,N′-bis(4-pyridylmethyl)oxalamide and acetic acid as a dihydrate, C14H14N4O2⋅2 C2H4O2⋅2 H2O
  84. Crystal structure of the co-crystal N,N′-bis(3-pyridylmethyl)oxalamide acetic acid (1/2), C14H14N4O2⋅2C2H4O2
  85. Crystal structure of the co-crystal N,N′-bis(4-pyridylmethyl)oxalamide and 2,3,5,6-tetrafluoro-1,4-di-iodobenzene (1/1), C14H14N4O2⋅C6F4I2
  86. Crystal structure of the co-crystal 4-[(4-carboxyphenyl)disulfanyl]benzoic acid–(1E,4E)-1-N,4-N-bis(pyridin-4-ylmethylidene)cyclohexane-1,4-diamine (1/1), C14H10O4S2⋅C18H20N4
  87. Crystal structure of hexacarbonyl-bis(μ2-di-n-propyldithiocarbamato-κ3S,S′:S;κ3S:S:S′)-di-rhenium(I), C20H28N2O6Re2S4
  88. Crystal structure of fac-tricarbonyl-morpholine-κN-(morpholinocarbamodithioato-κ2S,S′)rhenium(I), C12H17N2O5ReS2
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