Home Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4
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Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4

  • Lucky Dey , Saswata Rabi , Zinnat A. Begum ORCID logo , Tsugiko Takase , Ismail M. M. Rahman ORCID logo EMAIL logo , Edward R. T. Tiekink ORCID logo EMAIL logo and Tapashi Ghosh Roy EMAIL logo
Published/Copyright: July 21, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 5

Abstract

C22H24N4, triclinic, P 1 ‾ (no. 2), a = 9.217(4) Å, b = 9.774(4) Å, c = 10.843(4) Å, α = 96.770(2)°, β = 101.791(5)°, γ = 105.873(3)°, V = 903.9(6) Å3, Z = 2, R gt (F) = 0.0391, wR ref (F 2) = 0.1069, T = 93(2) K.

CCDC no.: 1902271

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: Yellow plate
Size: 0.20 × 0.20 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.08 mm−1
Diffractometer, scan mode: Rigaku Saturn724, ω
θ max, completeness: 27.5°, 99%
N(hkl)measured, N(hkl)unique, R int: 9263, 4078, 0.015
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3392
N(param)refined: 245
Programs: REQAB [1], CrystalClear [2], SHELX [3, 4], WinGX/ORTEP [5], Diamond [6]
Table 2:

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

Atom x y z U iso*/U eq
N1 0.27109 (12) 0.10660 (11) 0.66775 (10) 0.0213 (2)
H1N 0.3432 (14) 0.1715 (13) 0.6454 (13) 0.026*
N2 0.44043 (11) 0.20780 (10) 0.50519 (9) 0.0190 (2)
N3 0.68215 (12) 0.38152 (11) 0.69695 (9) 0.0209 (2)
H3N 0.5912 (12) 0.3434 (15) 0.7157 (13) 0.025*
N4 0.50957 (11) 0.28593 (11) 0.85799 (9) 0.0209 (2)
C1 0.21526 (13) −0.01888 (12) 0.58099 (11) 0.0218 (3)
C2 0.26238 (14) −0.02912 (12) 0.46907 (11) 0.0213 (2)
H2 0.217027 −0.118960 0.411109 0.026*
C3 0.37297 (13) 0.08140 (12) 0.42998 (11) 0.0199 (2)
C4 0.54675 (13) 0.32310 (12) 0.47286 (11) 0.0186 (2)
C5 0.67411 (13) 0.41255 (12) 0.57240 (11) 0.0191 (2)
C6 0.80638 (13) 0.38719 (12) 0.79100 (11) 0.0204 (2)
C7 0.78493 (14) 0.34181 (13) 0.90335 (11) 0.0214 (2)
H7 0.876047 0.349610 0.966936 0.026*
C8 0.63891 (14) 0.28408 (12) 0.93370 (11) 0.0208 (2)
C9 0.36310 (14) 0.23638 (13) 0.88525 (11) 0.0208 (2)
C10 0.23873 (14) 0.14242 (13) 0.78643 (11) 0.0207 (2)
C11 0.10744 (16) −0.15005 (14) 0.61062 (13) 0.0301 (3)
H11A 0.138388 −0.152307 0.702184 0.045*
H11B 0.113235 −0.237675 0.560349 0.045*
H11C 0.000499 −0.145565 0.588628 0.045*
C12 0.40622 (15) 0.03588 (13) 0.30291 (12) 0.0252 (3)
H12A 0.328630 0.049814 0.233011 0.038*
H12B 0.401159 −0.066419 0.292176 0.038*
H12C 0.510374 0.094803 0.301296 0.038*
C13 0.52665 (14) 0.36269 (13) 0.35216 (11) 0.0216 (2)
H13 0.438940 0.306934 0.285291 0.026*
C14 0.63225 (15) 0.48175 (13) 0.32812 (12) 0.0235 (3)
H14 0.617882 0.505392 0.244889 0.028*
C15 0.75840 (14) 0.56599 (13) 0.42533 (12) 0.0235 (3)
H15 0.831755 0.646520 0.408565 0.028*
C16 0.77771 (14) 0.53283 (13) 0.54722 (12) 0.0223 (3)
H16 0.862641 0.592897 0.614367 0.027*
C17 0.96784 (14) 0.43626 (15) 0.77105 (13) 0.0276 (3)
H17A 0.966101 0.397355 0.683044 0.041*
H17B 1.037648 0.401207 0.831353 0.041*
H17C 1.005088 0.542242 0.785754 0.041*
C18 0.64604 (16) 0.21514 (15) 1.05196 (12) 0.0288 (3)
H18A 0.683633 0.290989 1.128847 0.043*
H18B 0.717228 0.156673 1.053412 0.043*
H18C 0.541854 0.153173 1.050106 0.043*
C19 0.33197 (15) 0.28716 (14) 0.99972 (12) 0.0265 (3)
H19 0.413262 0.355817 1.064366 0.032*
C20 0.18454 (16) 0.23921 (15) 1.02078 (13) 0.0304 (3)
H20 0.166081 0.272235 1.100382 0.036*
C21 0.06437 (15) 0.14299 (15) 0.92525 (13) 0.0286 (3)
H21 −0.036135 0.108072 0.940215 0.034*
C22 0.08997 (14) 0.09731 (14) 0.80777 (12) 0.0253 (3)
H22 0.005723 0.034890 0.741353 0.030*

Source of material

The title macrocycle was isolated after a two-step procedure. Step 1: Preparation of the nickel(II) salt of the macrocycle. A solution of nickel(II) acetate tetrahydrate (2.00 g, 8.03 mmol) in butanol (10 mL) and 1,2-phenylenediamine (1.73 g, 16 mmol) in the same solvent (10 mL) were added to a solution of 2,4-pentanedione (1.7 mL, 16.6 mmol) in butanol (10 mL) in a 100 mL round bottom flask. The mixture was refluxed on a magnetic stirrer for 2–3 h. At this stage, the colour of the mixture was dark-green. After removing the flask from the heat source, the mixture was allowed to cool until just warm to the touch. Then, methanol (30 mL) was added, and the mixture was cooled in an ice-salt bath for at least 15 min to precipitate the purple crystalline product. After that, the mixture was filtered under vacuum and washed with methanol until the washings were colourless to pale-green. The obtained product (1.0 g) was suspended in absolute ethanol (30 mL) in a 100 mL round-bottom flask. A moderate stream of HCl gas was bubbled through the suspension with swirling occasionally. Caution was maintained as the mixture gets quite warm. Once a large quantity of bright-purple precipitate [H4(C22H22N4)][NiCl4], was formed, the mixture was filtered and washed with ethanol followed by diethyl ether. The yield was 95%.

Step 2: Isolation of the free macrocycle [H2(C22H22N4)]. The [H4(C22H22N4)][NiCl4] salt was dissolved in water (10 mL). Some water-insoluble white impurities were present at this stage which were removed by filtration. Solid NH4PF6 (1.0 g) was added to the filtrate which was swirled until a large amount of white precipitate formed. Then, the [H4(C22H22N4)][PF6]2 that had formed was filtered and washed with water until the product was pale-green. In this step, the by-product [NH4]2[NiCl4] was washed away to prevent nickel from re-inserting into the macrocycle upon basification; the large volume of water used resulted in some loss of the desired product. The sticky product [H4(C22H22N4)][PF6]2 that formed was transferred into a 50 mL beaker, rinsing with methanol to maximize the mass of product transferred. Triethylamine was added dropwise to this methanolic suspension with swirling. The bright-yellow free macrocycle [H2(C22H22N4)], crystallised immediately, filtered on a Büchner funnel, washed with methanol and dried in air. The yield was 57%. M. pt. (Microprocessor Melting Point Apparatus, SYSTONIC): 346 K. Elemental analysis (Leco CHNS-932 elemental analyzer) for C22H24N4: C, 76.70; H, 6.97; N, 16.30. Found: C, 76.62; H, 6.99; N, 16.41. IR (Shimadzu IR 20 spectrophotometer, KBr; cm−1): 3255 (w) ν(N–H), 1383 (s) ν(CH3), 1618 (s) and 1551 (s) ν(Ar C=C), 1364 (m) and 1187 (s) ν(Ar CN), 1027 (m) 743 (s) ν(Ar C–H). 1 H NMR (Bruker AVANCE 400 NMR spectrometer, DMSO, ppm): δ 2.16 (s, C(CH3), 12H), 4.91 (s, CH, 2H), 7.02 (m, Aromatic-H, 8H), 12.61 (br, N–H, 2H). 13 C{1 H} NMR (as for 1H NMR) δ: 8.64, 20.911 [C(CH3)], 97.98 [CH], 123.00 [N–C–CH3], 138.54 [Aromatic-C], 158.97 [N–C(Aromatic)]

Experimental details

The C-bound H atoms were geometrically placed (C–H = 0.95–1.00 Å) and refined as riding with U iso(H) = 1.2–1.5U eq(C). The N-bound atoms were located from a Fourier difference map and refined with N–H = 0.88 ± 0.01 Å, and with U iso(H) = 1.2U eq(N). Owing to poor agreement, one reflection, i.e. (2 1 1), was omitted from the final cycles of refinement.

Comment

Macrocyclic chemistry has sustained great fascination to scientists owing to its specific roles in different sectors of contemporary science. Thus, macrocyclic compounds are prominent in coordination chemistry [7], pharmacology [8, 9] as well as in crystal engineering [10]. These compounds also play a remarkable role in medicinal chemistry: as anti-cancer agents [11, 12], radioimmunotherapeutics [13] and as MRI contrast agents [14]. In this connection, researchers continue to report different types of macrocycles and their metal complexes [15], [16], [17], [18], [19], prepared by both the template and non-template methods. In continuation of these studies, herein the synthesis of a nickel(II) complex with a macrocyclic molecule of composition [H2(C22H22N4)] (I), by the template method and the subsequent isolation of the free macrocycle is described. It is noted that the crystal and molecular structures of (I) have been described previously [20]. However, disorder in the positions of the acidic hydrogen atoms precluded a definitive assignment of the putative tautomeric structure. As the authors noted in the Abstract to the paper: “A detailed structural interpretation of the free ligand is complicated by disorder involving degenerate tautomeric structures in the crystal lattice” [20]. The present, low-temperature structure determination of (I) allows a definitive assignment of the tautomeric structure as well as a detailed analysis of the molecular packing. The molecular structure of (I) is shown in figure (70% probably displacement ellipsoids). The molecule lacks symmetry and adopts a saddle-like conformation whereby the phenyl rings lie to one side of the N4-plane, forming a dihedral angle of 47.82(6)°, and with the remaining atoms lying to the other side of the N4 plane; the dihedral angle between the best planes through N1,N2,C1–C3 and N3,N4,C6–C8 atoms = 67.55(4)°. The molecular connectivity and conformation is as reported for the earlier determination [20]. However, the new analysis enables an unambiguous assignment of the tautomeric form of the molecule; no disorder was evident in the positions of the N-bound hydrogen atoms which are located on the N1 and N3 atoms. The imine bonds correspond to C3–N2 [1.3088(15) Å] and C8–N4 [1.3079(16) Å] with the bond lengths significantly shorter than the adjacent C4–N2 [1.4081(15) Å] and C9–N4 [1.4085(16) Å] bonds. The ethylene bonds correspond to C1–C2 [1.3718(18) Å] and C6–C7 [1.3776(17) Å] which are significantly shorter than the C2–C3 [1.4380(17) Å] and C7–C8 [1.4309(18) Å] single bonds. Intramolecular amine N–H⋯N(imine) hydrogen bonds stabilise the observed conformation [N1–H1n⋯N2: H1n⋯N2 = 1.937(14) Å, N1⋯N2 = 2.6856(19) Å with angle at H1n = 142.1(12)° and N3–H3n⋯N4: H3n⋯N4 = 1.926(13) Å, N3⋯N4 = 2.6756(19) Å with angle at H3n = 140.3(12)°]. In the molecular packing, following the distance criteria assumed in PLATON [21], the only directional interactions between molecules of (I) are π–π interactions occurring between centrosymmetrically related (C4,C5,C13–C16) rings [Cg(C4,C5,C13–C16)⋯Cg(C4,C5,C13–C16) i  = 3.5776(17) Å, with a slippage value = 1.171 Å for symmetry operation i: 1−x, 1−y, 1−z] to form a dimeric aggregate.

The lack of directional interactions in the crystal is supported by the analysis of the calculated Hirshfeld surfaces and of the full and delineated two-dimensional fingerprint plots. These were calculated with the program Crystal Explorer 17 [22] following literature methods [23]. The surface contacts are dominated by H⋯H contacts, contributing 67.3% of all contacts with significant contributions from C⋯H/H⋯C [22.6%] and N⋯H/H⋯N [6.3%]. The next most significant contributions to the surface contacts are from C⋯C [2.7%] and N⋯C/C⋯N [1.1%].

Corresponding author: Edward R. T. Tiekink, Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia, E-mail: ; and Ismail M. M. Rahman Institute of Environmental Radioactivity, Fukushima University, 1 Kanayagawa, Fukushima City, Fukushima 960-1296, Japan, E-mail: ; and Tapashi Ghosh Roy, Department of Chemistry, Faculty of Science, University of Chittagong, Chattogram 4331, Bangladesh, Email:

Funding source: Environmental Radioactivity Research Network Center

Award Identifier / Grant number: I-19-08

Award Identifier / Grant number: I-20-09

Award Identifier / Grant number: I-21-09

Funding source: Grants-in-Aid for Scientific Research

Award Identifier / Grant number: 21K12287

Funding source: Japan Society for the Promotion of Science doi.org/10.13039/501100001691

Funding source: Science and Technology Research Partnership for Sustainable Development doi.org/10.13039/501100009037

Funding source: Japan Science and Technology Agency

Funding source: Japan International Cooperation Agency

Funding source: Sunway University doi.org/10.13039/501100010798

Award Identifier / Grant number: GRTIN-IRG-01-2021

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

  2. Research funding: This study was supported by the Science and Technology Research Partnership for Sustainable Development (SATREPS) in collaboration with the Japan Science and Technology Agency (JST) and the Japan International Cooperation Agency (JICA) (Grant No. JPMJSA1603), the Environmental Radioactivity Research Network Center at Fukushima University, Japan (Grant Nos I-19-08, I-20-09 and I-21-09), Grants-in-Aid for Scientific Research from the Japan Society for the Promotion of Science (JSPS) (Grant No. 21K12287) and Sunway University Sdn Bhd (Grant No. GRTIN-IRG-01–2021).

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

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Received: 2021-06-15
Accepted: 2021-07-06
Published Online: 2021-07-21
Published in Print: 2021-09-27

© 2021 Lucky Dey 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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  21. Crystal structure of bis(µ2- 4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(µ2-1-(4-pyridyl)piperazine-κ2N:N′)-hexa-aqua-tetra-copper(II), C46H46Cu4I4N10O22
  22. Crystal structure of poly[diaqua-(μ2-2,5-dihydroxyterephthalato-κ2O:O′)(μ2-bis(4-pyridylformyl)piperazine-κ2N:N′)cadmium(II)] dihydrate, C24H28CdN4O12
  23. Crystal structure of poly[aqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(μ3-2,3,5,6-tetrafluoroterephthalato-κ3O:O′:O′′)cadmium(II)], C17H14N4O5F4Cd
  24. Crystal structure of 6-(quinolin-8-yl)benzo[a]phenanthridin-5(6H)-one, C26H16N2O
  25. The crystal structure of aqua-bis(6-chloropicolinato-κ2N,O)copper(II), C12H8Cl2N2O5Cu
  26. Crystal structure of catena-poly[diaqua-bis(μ2-4,4′-bipyridyl-κ2N:N′) disilver(I)] 4-oxidopyridine-3-sulfonate trihydrate, C25H29Ag2N5O9S
  27. The crystal structure of 4-(3-bromophenyl)pyrimidin-2-amine, C10H8BrN3
  28. Crystal structure of 6-oxo-4-phenyl-1-propyl-1,6-dihydropyridine-3-carbonitrile, C15H14N2O
  29. Crystal structure of 4-(2,2-difluoroethyl)-2,4-dimethyl-6-(trifluoromethyl)isoquinoline-1,3(2H,4H)-dione, C14H12F5NO2
  30. Crystal structure of dibromido-(1-methyl-1H-imidazole-κ1N)-(3-(3-methyl-1H-imidazol-3-ium-1-yl)propanoato-κ1O)zinc(II), C11H16Br2N4O2Zn
  31. The crystal structure of 1,1′-(((2 (dimethylamino)ethyl)azanediyl)bis(methylene)) bis(naphthalen-2-olato-κ4 N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)- titanium(IV) ─ dichloromethane (2/1), C33H29N3O6Ti
  32. The layered crystal structure of bis(theophyllinium) hexachloridostannate (IV), C14H18N8O8SnCl6
  33. The crystal structre of 3-(1-ethenyl-1H-imidazol-3-ium-3-yl)propane-1-sulfonate, C8H12N2O3S
  34. Synthesis and crystal structure of di-tert-butyl 1″-acetyl-2,2″,9′-trioxo-4a′,9a′-dihydro-1′H,3′H,9′H-dispiro[indoline-3,2′-xanthene-4′,3″-indoline]-1,3′-dicarboxylate, C39H38N2O9
  35. The crystal structure of 4-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  36. The crystal structure of 1-fluoro-4-(p-tolylethynyl)benzene, C15H11F
  37. The crystal structure of bis[4-bromo-2-(1H-pyrazol-3-yl) phenolato-κ2N,O] copper(II), C18H12Br2CuN4O2
  38. The crystal structure of poly[(μ 3-imidazolato-κ 3 N:N:N′)(tetrahydrofuran- κ 1 O)lithium(I)], C7H11LiN2O
  39. Crystal structure of N′,N′′′-((1E,1′E)-(propane-2,2-diylbis(1H-pyrrole-5,2diyl))bis(methaneylylidene))di(nicotinohydrazide) pentahydrate, C25H24N8O2·5H2O
  40. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-ethyl-1H-imidazol-3-ium hexafluoridophos-phate(V), C9H15F6N2O2P
  41. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(3-thiophenecarboxylato-κ2O,O′)copper(II), C22H14N2O4S2Cu
  42. The crystal structure of 2-amino-3-carboxypyridin-1-ium iodide hemihydrate, C6H8IN2O2.5
  43. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-2-yl)methylene)-tetralone, C18H17NO3
  44. The crystal structure of [μ-hydroxido-bis[(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)-tricarbonylrhenium(I)] bromide hemihydrate, C30H26N4O9Re2Br
  45. The crystal structure of 2,5-bis(3,5-dimethylphenyl)thiazolo[5,4-d]thiazole, C20H18N2S2
  46. The crystal structure of 5-benzoyl-1-[(E)-(4-fluorobenzylidene)amino]-4-phenylpyrimidin-2(1H)-one, C24H16FN3O2
  47. Crystal structure of monocarbonyl(N-nitroso-N-oxido-phenylamine-κ 2 O,O′)(tricyclohexylphosphine-κP)rhodium(I), C25H39N2O3PRh
  48. Crystal structure of poly[bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N:N′:N″]nickel(II)] hexafluorosilicate, C36H36N12NiSiF6
  49. The crystal structure of 13-(pyrazole-1-yl-4-carbonitrile)-matrine, C19H25N5O
  50. Crystal structure of 3,5-bis((E)-4-methoxy-2-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  51. The crystal structure of N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide, C26H22N4O2S2
  52. Crystal structure of (E)-7-fluoro-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  53. Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2
  54. The crystal structure of cis-diaqua-bis (N-butyl-N-(pyridin-2-yl)pyridin-2-amine-κ2N,N′)cobalt(II)] dichloride trihydrate, C28H44Cl2N6O5Co
  55. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C18H17NO3
  56. Crystal structure of (E)-2-((3-fluoropyridin-4-yl)methylene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  57. The crystal structure of 6-bromohexanoic acid, C6H11BrO2
  58. The crystal structure of 4-chloro-thiophenol, C6H5ClS
  59. The crystal structure of 4-bromobenzyl chloride, C7H6BrCl
  60. The crystal structure of di-tert-butyl dicarbonate, C10H18O5
  61. The crystal structure of (2-(4-chlorophenyl)-5-methyl-1,3-dioxan-5-yl)methanol, C12H15ClO3
  62. The crystal structure of the co-crystal: 2-hydroxybenzoic acid – N′-(butan-2-ylidene)pyridine-4-carbohydrazide, C10H13N3O·C7H6O3
  63. Crystal structure and anti-inflammatory activity of (E)-7-fluoro-2-((5-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  64. Crystal structure of (E)-7-fluoro-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  65. Crystal structure of 1,1′-(butane-1,4-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C32H56F24N8P4
  66. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2)-cadmium(II), C14H20CdCl2N4O4
  67. Crystal structure of 1-(2-cyanobenzyl)-3-cyano-4-phenyl-4-(2-cyanobenzyl)-1,4-dihydropyridine monohydrate, C56H42N8O
  68. The crystal structure of 3-(carboxymethyl)-1-ethenyl-1H-imidazol-3-ium chloride, C7H9N2O2Cl
  69. The crystal structure of adamantylmethoxydiphenylsilane, C23H28OSi
  70. Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4
  71. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H15NO3
  72. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)cobalt(II)] dinitrate, C18H28N10O8Co
https://doi.org/10.1515/ncrs-2021-0244
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of [aqua-(4-iodopyridine-2,6-dicarboxylato-κ3 O,N,O′)-(1,10-phenanothroline-κ2 N,N′)copper(II)] dihydrate, C19H16O7N3CuI
  4. The crystal structure of tetrakis(1-isopropyl-1H-imidazolium) octamolybdate, C24H44Mo8N8O26
  5. Crystal structure of catena-poly[bis(µ2-3,5-bis(1-imidazolyl)pyridine-κ2 N:N′)-(µ2-3-nitrophthalato-k3 O,O′:O″)cadmium(II)] dihydrate, C30H25N11O8Cd
  6. The crystal structure of diaqua-bis(2-(3-(1H-pyrazol-4-yl)-1H-1,2,4-triazol-5-yl)pyridine-κ2 N:N′)-bis(3,5-dicarboxybenzoato-κ1 O)cobalt(II), C38H30CoN12O14
  7. Crystal structure of the nickel(II) complex aqua-(2,6-di(pyrazin-2-yl)-4,4′-bipyridine-κ3 N,N′,N′′)-(phthalato-κ2 O,O′)nickel(II) tetrahydrate, C26H26N6O9Ni
  8. The crystal structure of 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-methylmethanaminium 3-carboxyprop-2-enoate, C21H20FN3O6S
  9. The crystal structure of 1,2-bis(4-pyridyl)ethane - 4,4-dihydroxydiphenylmethane (1/1), C25H21N2O2
  10. Crystal structure of bis(2-((E)-5-chloro-2-hydroxybenzylidene)hydrazineyl)methaniminium trifluoroacetate dihydrate, C34H36Cl4N10O12
  11. Crystal structure of 1-cyclopropyl-7-ethoxy-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C15H13F2NO4
  12. Crystal structure of methyl 3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)benzoate, C18H15BN2O2
  13. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-2-hydroxybenzohydrazide, C14H11ClN2O3
  14. Crystal structure of Al-rich fluorophlogopite, K1.0(Mg2.8Al0.2)(Si2.8Al1.2)O10F2
  15. The crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium hexafluoridoantimonate(V), C20H22F6I2N3Sb
  16. Crystal structure of tris(3-iodopyridin-1-ium) catena-poly[(hexachlorido-κ1 Cl)-(μ2-trichlorido-κ2 Cl:Cl)diantimony(III)], C15H15Cl9I3N3Sb2
  17. Crystal structure of methyl 2-(1H-naphtho[1,8-de][1.3.2]diazaborinin-2(3H-yl)benzoate C18H15BN2O2
  18. The crystal structure of 1,8-bis(4-methoxybenzoyl)naphthalene-2,7-diyl dibenzoate, C40H28O8
  19. Crystal structure of 2-bromo-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C14H15B2BrF4N4
  20. The crystal structure of (E)-3-chloro-2-(2-(2-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  21. Crystal structure of bis(µ2- 4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(µ2-1-(4-pyridyl)piperazine-κ2N:N′)-hexa-aqua-tetra-copper(II), C46H46Cu4I4N10O22
  22. Crystal structure of poly[diaqua-(μ2-2,5-dihydroxyterephthalato-κ2O:O′)(μ2-bis(4-pyridylformyl)piperazine-κ2N:N′)cadmium(II)] dihydrate, C24H28CdN4O12
  23. Crystal structure of poly[aqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(μ3-2,3,5,6-tetrafluoroterephthalato-κ3O:O′:O′′)cadmium(II)], C17H14N4O5F4Cd
  24. Crystal structure of 6-(quinolin-8-yl)benzo[a]phenanthridin-5(6H)-one, C26H16N2O
  25. The crystal structure of aqua-bis(6-chloropicolinato-κ2N,O)copper(II), C12H8Cl2N2O5Cu
  26. Crystal structure of catena-poly[diaqua-bis(μ2-4,4′-bipyridyl-κ2N:N′) disilver(I)] 4-oxidopyridine-3-sulfonate trihydrate, C25H29Ag2N5O9S
  27. The crystal structure of 4-(3-bromophenyl)pyrimidin-2-amine, C10H8BrN3
  28. Crystal structure of 6-oxo-4-phenyl-1-propyl-1,6-dihydropyridine-3-carbonitrile, C15H14N2O
  29. Crystal structure of 4-(2,2-difluoroethyl)-2,4-dimethyl-6-(trifluoromethyl)isoquinoline-1,3(2H,4H)-dione, C14H12F5NO2
  30. Crystal structure of dibromido-(1-methyl-1H-imidazole-κ1N)-(3-(3-methyl-1H-imidazol-3-ium-1-yl)propanoato-κ1O)zinc(II), C11H16Br2N4O2Zn
  31. The crystal structure of 1,1′-(((2 (dimethylamino)ethyl)azanediyl)bis(methylene)) bis(naphthalen-2-olato-κ4 N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)- titanium(IV) ─ dichloromethane (2/1), C33H29N3O6Ti
  32. The layered crystal structure of bis(theophyllinium) hexachloridostannate (IV), C14H18N8O8SnCl6
  33. The crystal structre of 3-(1-ethenyl-1H-imidazol-3-ium-3-yl)propane-1-sulfonate, C8H12N2O3S
  34. Synthesis and crystal structure of di-tert-butyl 1″-acetyl-2,2″,9′-trioxo-4a′,9a′-dihydro-1′H,3′H,9′H-dispiro[indoline-3,2′-xanthene-4′,3″-indoline]-1,3′-dicarboxylate, C39H38N2O9
  35. The crystal structure of 4-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  36. The crystal structure of 1-fluoro-4-(p-tolylethynyl)benzene, C15H11F
  37. The crystal structure of bis[4-bromo-2-(1H-pyrazol-3-yl) phenolato-κ2N,O] copper(II), C18H12Br2CuN4O2
  38. The crystal structure of poly[(μ 3-imidazolato-κ 3 N:N:N′)(tetrahydrofuran- κ 1 O)lithium(I)], C7H11LiN2O
  39. Crystal structure of N′,N′′′-((1E,1′E)-(propane-2,2-diylbis(1H-pyrrole-5,2diyl))bis(methaneylylidene))di(nicotinohydrazide) pentahydrate, C25H24N8O2·5H2O
  40. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-ethyl-1H-imidazol-3-ium hexafluoridophos-phate(V), C9H15F6N2O2P
  41. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(3-thiophenecarboxylato-κ2O,O′)copper(II), C22H14N2O4S2Cu
  42. The crystal structure of 2-amino-3-carboxypyridin-1-ium iodide hemihydrate, C6H8IN2O2.5
  43. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-2-yl)methylene)-tetralone, C18H17NO3
  44. The crystal structure of [μ-hydroxido-bis[(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)-tricarbonylrhenium(I)] bromide hemihydrate, C30H26N4O9Re2Br
  45. The crystal structure of 2,5-bis(3,5-dimethylphenyl)thiazolo[5,4-d]thiazole, C20H18N2S2
  46. The crystal structure of 5-benzoyl-1-[(E)-(4-fluorobenzylidene)amino]-4-phenylpyrimidin-2(1H)-one, C24H16FN3O2
  47. Crystal structure of monocarbonyl(N-nitroso-N-oxido-phenylamine-κ 2 O,O′)(tricyclohexylphosphine-κP)rhodium(I), C25H39N2O3PRh
  48. Crystal structure of poly[bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N:N′:N″]nickel(II)] hexafluorosilicate, C36H36N12NiSiF6
  49. The crystal structure of 13-(pyrazole-1-yl-4-carbonitrile)-matrine, C19H25N5O
  50. Crystal structure of 3,5-bis((E)-4-methoxy-2-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  51. The crystal structure of N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide, C26H22N4O2S2
  52. Crystal structure of (E)-7-fluoro-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  53. Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2
  54. The crystal structure of cis-diaqua-bis (N-butyl-N-(pyridin-2-yl)pyridin-2-amine-κ2N,N′)cobalt(II)] dichloride trihydrate, C28H44Cl2N6O5Co
  55. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C18H17NO3
  56. Crystal structure of (E)-2-((3-fluoropyridin-4-yl)methylene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  57. The crystal structure of 6-bromohexanoic acid, C6H11BrO2
  58. The crystal structure of 4-chloro-thiophenol, C6H5ClS
  59. The crystal structure of 4-bromobenzyl chloride, C7H6BrCl
  60. The crystal structure of di-tert-butyl dicarbonate, C10H18O5
  61. The crystal structure of (2-(4-chlorophenyl)-5-methyl-1,3-dioxan-5-yl)methanol, C12H15ClO3
  62. The crystal structure of the co-crystal: 2-hydroxybenzoic acid – N′-(butan-2-ylidene)pyridine-4-carbohydrazide, C10H13N3O·C7H6O3
  63. Crystal structure and anti-inflammatory activity of (E)-7-fluoro-2-((5-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  64. Crystal structure of (E)-7-fluoro-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  65. Crystal structure of 1,1′-(butane-1,4-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C32H56F24N8P4
  66. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2)-cadmium(II), C14H20CdCl2N4O4
  67. Crystal structure of 1-(2-cyanobenzyl)-3-cyano-4-phenyl-4-(2-cyanobenzyl)-1,4-dihydropyridine monohydrate, C56H42N8O
  68. The crystal structure of 3-(carboxymethyl)-1-ethenyl-1H-imidazol-3-ium chloride, C7H9N2O2Cl
  69. The crystal structure of adamantylmethoxydiphenylsilane, C23H28OSi
  70. Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4
  71. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H15NO3
  72. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)cobalt(II)] dinitrate, C18H28N10O8Co
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