Startseite Crystal structure of ethyl 4-{[5-(adamantan-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,4-oxadiazol-3-yl]methyl}piperazine-1-carboxylate, C20H30N4O3S
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Crystal structure of ethyl 4-{[5-(adamantan-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,4-oxadiazol-3-yl]methyl}piperazine-1-carboxylate, C20H30N4O3S

  • Mohammad M. Al-Sanea , Mohammed S. M. Abdelbaky , Santiago Garcia-Granda , Ahmed A. B. Mohamed , Edward R. T. Tiekink ORCID logo und Ali A. El-Emam ORCID logo EMAIL logo
Veröffentlicht/Copyright: 17. Februar 2023
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 238 Heft 2

Abstract

C20H30N4O3S, orthorhombic, P212121 (no. 19), a = 7.7152(3) Å, b = 10.6132(2) Å, c = 25.5990(7) Å, V = 2096.12(11) Å3, Z = 4, Rgt(F) = 0.0579, wRref(F2) = 0.1216, T = 293 K.

CCDC no.: 2220806

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 prism
Size: 0.15 × 0.08 × 0.06 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 1.60 mm−1
Diffractometer, scan mode: Xcalibur, ω
θmax, completeness: 75.5°, >99%
N(hkl)measured, N(hkl)unique, Rint: 11,877, 4126, 0.092
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2199
N(param)refined: 255
Programs: CrysAlisPRO [1], SHELX [2, 3], WinGX/ORTEP [4]
Table 2:

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

Atom x y z Uiso*/Ueq
S1 0.1081 (3) 0.11839 (14) 0.50448 (7) 0.0644 (5)
O1 0.1475 (5) 0.3490 (3) 0.54356 (13) 0.0435 (11)
O2 0.6704 (7) 0.4683 (5) 0.2698 (2) 0.0857 (18)
O3 0.7237 (6) 0.2641 (4) 0.28874 (18) 0.0669 (14)
N1 0.0822 (7) 0.3523 (4) 0.46190 (17) 0.0432 (13)
N2 0.1013 (7) 0.4778 (4) 0.47689 (17) 0.0456 (13)
N3 0.1571 (7) 0.3257 (4) 0.36927 (17) 0.0448 (13)
N4 0.4768 (7) 0.3520 (5) 0.31556 (19) 0.0529 (14)
C1 0.1114 (8) 0.2735 (5) 0.5010 (2) 0.0457 (15)
C2 0.1381 (8) 0.4717 (5) 0.5254 (2) 0.0400 (15)
C3 0.1660 (9) 0.5765 (5) 0.5633 (2) 0.0430 (16)
C4 0.2404 (9) 0.6903 (5) 0.5339 (2) 0.0552 (18)
H4A 0.161796 0.715283 0.506199 0.066*
H4B 0.350728 0.668022 0.518220 0.066*
C5 −0.0089 (9) 0.6138 (5) 0.5865 (2) 0.0537 (17)
H5A −0.058813 0.542338 0.604743 0.064*
H5B −0.087601 0.637966 0.558710 0.064*
C6 0.2892 (9) 0.5392 (5) 0.6073 (2) 0.0587 (19)
H6A 0.401035 0.516182 0.592842 0.070*
H6B 0.243153 0.466755 0.625773 0.070*
C7 0.2658 (10) 0.8012 (6) 0.5726 (2) 0.065 (2)
H7 0.314267 0.873748 0.553936 0.078*
C8 0.0893 (10) 0.8362 (5) 0.5950 (2) 0.066 (2)
H8A 0.011529 0.859965 0.566865 0.079*
H8B 0.101189 0.907683 0.618311 0.079*
C9 0.0140 (10) 0.7244 (6) 0.6247 (3) 0.064 (2)
H9 −0.098563 0.747531 0.639595 0.077*
C10 0.1367 (10) 0.6851 (6) 0.6681 (2) 0.073 (2)
H10A 0.151016 0.754043 0.692656 0.088*
H10B 0.088607 0.613787 0.686872 0.088*
C11 0.3109 (11) 0.6497 (6) 0.6452 (3) 0.066 (2)
H11 0.389491 0.624909 0.673485 0.080*
C12 0.3879 (9) 0.7628 (6) 0.6160 (3) 0.073 (2)
H12A 0.404221 0.832555 0.639964 0.088*
H12B 0.499828 0.740318 0.601500 0.088*
C13 0.0261 (8) 0.3221 (5) 0.4087 (2) 0.0498 (17)
H13A −0.024324 0.238347 0.408910 0.060*
H13B −0.064828 0.380629 0.398907 0.060*
C14 0.2987 (8) 0.2351 (5) 0.3778 (2) 0.0508 (17)
H14A 0.250556 0.152735 0.385552 0.061*
H14B 0.367874 0.261554 0.407432 0.061*
C15 0.4125 (9) 0.2265 (5) 0.3296 (2) 0.0567 (19)
H15A 0.509597 0.170853 0.336447 0.068*
H15B 0.346406 0.191791 0.300770 0.068*
C16 0.2283 (9) 0.4503 (6) 0.3588 (2) 0.0539 (18)
H16A 0.296960 0.477898 0.388362 0.065*
H16B 0.134614 0.509982 0.353791 0.065*
C17 0.3405 (9) 0.4466 (6) 0.3103 (2) 0.0575 (19)
H17A 0.269224 0.427038 0.280196 0.069*
H17B 0.392417 0.528749 0.304798 0.069*
C18 0.6274 (10) 0.3705 (7) 0.2896 (2) 0.0591 (19)
C19 0.8821 (9) 0.2727 (7) 0.2597 (3) 0.074 (2)
H19A 0.954220 0.339919 0.273370 0.088*
H19B 0.858286 0.289490 0.223196 0.088*
C20 0.9707 (9) 0.1484 (6) 0.2658 (3) 0.079 (2)
H20A 1.078741 0.149615 0.247265 0.119*
H20B 0.898099 0.082937 0.251960 0.119*
H20C 0.992039 0.132635 0.302201 0.119*

Source of material

37% Formaldehyde solution (1.5 mL) and ethyl piperazine-1-carboxylate (1.58 g, 0.01 mole) were added to a solution of 5-(adamantan-1-yl)-1,3,4-oxadiazole-2(3H)-thione [5] (2.36 g, 0.01 mol), in ethanol (15 mL) and the mixture was stirred for 2 h at 298 K (room temperature) and allowed to stand overnight. Cold water (5 mL) was drop-wisely added with continuous stirring for an additional 30 min. at room temperature. The precipitated crude product was filtered, washed with cold water, dried and crystallised from EtOH/H2O to yield 3.09 g (76%) of the title compound as colourless prisms. Melting point: 391–393 K (uncorrected). IR, ν (cm−1): 1246 (C–O–C), 1362 (C=S), 1607, 1455 (C=N), 1692 (C=O), 2855, 2925, 2995 (CH3, CH2, CH). 1 H NMR (250 MHz, CDCl3): δ 4.99 (2H, NCH2N, s), 4.11 (CH2CH3, 2H, q), 3.49 (Piperazine-H, 4H, t), 2.77 (Piperazine-H, 4H, t), 2.11 (Adamantane-H, 3H, s), 1.99 (Adamantane-H, 6H, s), 1.74 (Adamantane-H, 6H, q), 1.25 (CH3, 3H, t). 13 C NMR (62.9 MHz, CDCl3): δ 178.56 (C=S), 167.96 (C=N), 155.41 (C=O), 70.01 (NCH2N), 61.45, 50.08 (Piperazine-C), 43.20 (CH2CH3), 39.09, 36.08, 34.40, 27.45 (Adamantane-C), 14.65 (CH3). Slow evaporation of a C2H5OH:CHCl3 (2:1, v/v) solution of the compound at room temperature afforded suitable single crystals which were used for the X-ray diffraction study.

Experimental details

The C-bound H atoms were geometrically placed (C–H = 0.96–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The sample was refined as a two-component inversion twin.

Comment

The 1,3,4-oxadiazole nucleus comprises the core pharmacophore of several bioactive compounds [6, 7] with marked chemotherapeutic properties such as antineoplastic [8] and anti-microbial [9] activities. Furthermore, adamantane-containing compounds have long been recognised for their chemotherapeutic activities, such as anti-viral, anti-bacterial and antineoplastic activities [10, 11]. Thus, the title oxadiazole/adamantane hybrid compound, (I), was studied in this context.

The molecular structure of (I) is shown in the figure (35% probability ellipsoids). The central 1,3,4-oxadiazolyl-2-thione ring is substituted at the N1-position by a methylene substituent bearing a ethyl piperazine-1-carboxylate group, and at the C2-position by a adamantanyl group. The five-membered ring is strictly planar with a r.m.s. deviation of the fitted atoms being 0.0051 Å; the maximum deviation from the least-squares plane is 0.007(4) Å for atom N1. The attached atoms, i.e. S1, C3 and C13. lie −0.010(9), 0.053(11) and 0.102(10) Å out of the plane, respectively. When the molecule of (I) is viewed side-on in line with the plane through the five-membered ring, the adamantyl atoms C5, C8, C9 and C10 clearly lie to one side of the plane, and the ethyl piperazine-1-carboxylate group to the other side. Within the central ring, the short C2–N2 bond length [1.275(6) Å] is indicative of significant double-bond character compared with C1–N1 [1.323(7) Å]. The N1–N2 [1.394(6) Å] as well as the experimentally equivalent C1–O1 and C2–O1 [1.381(6) & 1.385(6) Å] bond lengths are all consistent with limited delocalisation of π-electron density within the ring; the C1=S1 bond length is 1.649(5) Å.

While there are several examples of crystal structures where a central 1,3,4-oxadiazolyl-2-thione ring is substituted at the N1- and C2-positions, e.g. with (4-phenylpiperazin-1-yl)methylene and 2-thienyl groups [12], there is also a very closely related example bearing (4-phenylpiperazin-1-yl)methylene and adamantyl substituents [13]. In the latter, a very similar molecular conformation is found except the adamantyl substituent is disposed evenly about the plane through the central residue. Also, the bond lengths within the five-membered ring resembles closely those in (I), most notably the double-bond character of the C2–N2 bond [1.288(7) Å].

The molecular packing in the crystal of (I) is largely devoid of directional interactions. Side-on contacts between the thione-S1 atom approaching either side of the five-membered ring are apparent [C1=S1⋯Cg(O1,N1,N2,C1,C2) i : S1⋯Cg(O1,N1,N2,C1,C2) i  = 3.799(3) Å with angle at S1 = 91.3(2)° and C1=S1⋯Cg(O1,N1,N2,C1,C2) ii : S1⋯Cg(O1,N1,N2,C1,C2) ii  = 3.923(3) Å with angle at S1 = 89.5(2)° for symmetry operations (i) −1/2 + x, 1/2 − y, 1 − z and (ii) 1/2 + x, 1/2 − y, 1 − z]. Thus, the S1 atom bridges two rings. These contacts feature within a flat, supramolecular tape along the a-axis. The connections between the tapes within the three-dimensional architecture are close H⋯H contacts [C17–H17a⋯H20b iii –C20 iii  = 2.25 Å with angles at H17a and H20 of 117 and 179°, respectively, for (iii) 1 − x, 1/2 + y, 1/2 − z]. Globally, when viewed down the a-axis, the molecules are arranged to define columns in which reside the adamantanyl groups.

A further analysis of the molecular packing was conducted with the aid of the calculation of the Hirshfeld surfaces and fingerprint plots [14, 15]. As anticipated for molecules bearing adamantyl residues [16], there is a clear dominance of contacts involving H. In the present case, interactions involving H contribute 97.2% to the overall surface, i.e. 68.6% [H⋯H], 13.1% [O⋯H/H⋯O], 9.5% [S⋯H/H⋯S], 3.6% [N⋯H/H⋯N] and 2.4% [C⋯H/H⋯C]. The next most notable contribution is 1.2% for S⋯N/N⋯S contacts. The presence of a close H⋯H contact referred to above is evidenced by a pair of symmetric peaks at d i  + d e at ca 2.22 Å.

Corresponding author: Ali A. El-Emam, Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt, E-mail:

Funding source: Deanship of Scientific Research at Jouf University

Award Identifier / Grant number: DSR-2021-01-03116

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

  2. Research funding: Deanship of Scientific Research at Jouf University under grant no. DSR-2021-01-03116.

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

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Received: 2022-11-20
Accepted: 2023-01-10
Published Online: 2023-02-17
Published in Print: 2023-04-25

© 2022 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of methyl 2-((4-chloro-2-fluoro-6-((2,2,2-trifluoroethyl) thio)phenoxy)methyl)benzoate, C17H13ClF4O3S
  4. The crystal structure of 3-hydroxy-5-oxo-4-propanoylcyclohex-3-ene-1-carboxylic monohydrate, C10H14O6
  5. Crystal structure of 2-({[5-(adamantan-2-yl)-2-sulfanylidene-1,3,4-oxadiazolidin-3-yl]methyl}amino)benzonitrile, C20H22N4OS
  6. Crystal structure of 1-(3-bromopropyl)-2-((4-chlorophenoxy)methyl)-4-methyl-1H-benzo[d]imidazole, C18H18BrClN2O
  7. Crystal structure of 2-methoxy-6-[(2-morpholin-4-yl-phenylamino)-methylene]-4-nitro-cyclohexa-2,4-dienone, C18H19N3O5
  8. The crystal structure of 2-(7-(2,3-dimethoxyphenyl)-[1,2,4]triazolo[1,5-a]-pyrimidin-5-yl)-3-methoxyphenol, C20H18N4O4
  9. The crystal structure of 3-(1-(2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazinyl)ethylidene)chroman-2,4-dione dihydrate, C20H22N2O8
  10. Crystal structure of 3,5,7-trimethoxy-3′,4′-methylenedioxy-flavone, C19H16O7
  11. The crystal structure of strictic acid, C20H26O3
  12. Crystal structure of 1,1′-(pyrazine-1,4-diyl)-bis(propan-2-one), C10H14N2O2
  13. The crystal structure of 1-(adamantan-1-yl)-3-(4-chlorophenyl)urea, C17H21ClN2O
  14. The crystal structure of (2R,6′R)-2′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-2′-ene-3,4′-dione, C16H14Cl2O5
  15. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-3-((4-methoxyphenyl)amino)-10,13-dimethylhexadecahydro-1H-cyclopenta[α]-phenanthren-17-yl)ethan-1-one, C28H41NO2
  16. Crystal structure of N-2,6-difluorobenzoyl-N′-[1-(3-chloro-4-methyl-phenyl)-4-cyano-1H-pyrazol-5-carbamoyl]urea, C19H12ClF2N5O2
  17. Crystal structure of (−)-β-D-19-glucopiranosyl-9,15-dihydroxy kaurenoate, C26H40O9
  18. Crystal structure of 7-hydroxy-6-(2-hydroxyethyl)-2H-chromen-2-one, C11H10O4
  19. Crystal structure of S-(benzo[d]thiazol-2-yl)-N-(tert-butyl)thiohydroxylamine, C11H14N2S2
  20. Crystal structure of poly[di-µ2-aqua-aqua-nitrato-κ2O,O′-(µ3-2-nitroisophthalato-κ4O,O′:O″:O′″)barium(II)natrium(II)] monohydrate, C8H11BaN2NaO13
  21. The crystal structure of diaqua-bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2 N,O)-cobalt(II) dihydrate, C14H16N6O8Co
  22. Crystal structure of (S,E)-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-4-yl)-2,3- dihydroquinazolin-4(1H)-one monohydrate, C19H15N5O⋅H2O
  23. Synthesis and crystal structure of 5-(8-(((5-carboxypentyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxy-3-nitrobenzenesulfonate monohydrate, C22H24N2O12S
  24. Synthesis and crystal structure of 8-bromo-3-(1H-pyrazole-1-carbonyl)-2H-chromen-2-one, C13H7BrN2O3
  25. Crystal structure of E-7-fluoro-2-(4-methoxy-3-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  26. Hydrogen bonded dimers in the crystal structure of 2-chloro-N-((3,5-dimethylphenyl)carbamoyl)-nicotinamide, C30H28Cl2N6O4
  27. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-allyl-1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C10H12F6N2P
  28. Crystal structure of (E)-7-bromo-2-(4-(4-methylpiperazin-1-yl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23BrN2O
  29. Crystal structure of pentacarbonyl-(μ2-ethane-1,2-dithiolato-κ4S:S,S′:S′)-(diphenyl(o-tolyl)phosphine-κ1P)diiron (Fe–Fe), C26H21Fe2O5PS2
  30. Crystal structure of 9-(2-chloroethoxy)-4-(4-methoxy-3-(trifluoromethyl)phenyl)- 5,6-dihydrobenzo[h]quinazolin-2-amine, C22H19ClF3N3O2
  31. Crystal structure of triaqua-[5-bromo-2-(carboxylatomethoxy)benzoate-κ3 O,O′,O″]nickel(II), C9H11BrNiO8
  32. The crystal structure of 4,4′-dichloro-3,5′-diphenyl-1′H-1,3′- bipyrazole, C18H12Cl2N4
  33. The crystal structure of bis(1H-pyrazole-carboxamidine-κN,N′)bis(nitrato-κO)-copper(II), C8H12CuN10O6
  34. Synthesis and crystal structure of 3-bromo-4-phenyl-2H-chromene, C15H11BrO
  35. Crystal structure of (E)-5-(diethylamino)-2-((morpholinoimino)methyl)phenol, C15H23N3O2
  36. Crystal structure of niobium trigallide, NbGa3
  37. Crystal structure of dimethyl 4,4′-(((1R, 2R)-cyclohexane-1,2-diyl)bis(azanediyl))dibenzoate, C22H26N2O4
  38. Crystal structure of dimethyl 4,4′-((4R, 5R)-4,5-diphenylimidazolidine-1,3-diyl)dibenzoate, C31H28N2O4
  39. The crystal structure of 2-(2-bromophenyl)-4-phenylbenzo[b][1,4]oxaphosphinine 4-oxide, C20H14BrO2P
  40. The crystal structure of 3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one, C18H21NO4
  41. Crystal structure of catena-poly[[μ2-1,3-bis[(1H-imidazol-1- yl)methyl]benzene-N:N′]-(μ2–D–camphorato-O, O′: O″, O‴)cadmium(II)], C48H56Cd2N8O8
  42. Crystal structure of N-(4-bromophenyl)-4-[3-(trifluoromethyl)phenyl]-piperazine-1-carbothioamide, C18H17BrF3N3S
  43. The crystal structure of cis-Dicyano-bis(2,2′-bipyridine)k2N,N′-chromium(III) hexafluorophosphate, C22H16N6F6PCr
  44. Crystal structure of 4-((6-bromohexyl)oxy)-2-hydroxybenzaldehyde, C13H17BrO3
  45. Crystal structure of hydrazinium methanesulfonate, CH8N2O3S
  46. Crystal structure of 1-(2-iodobenzoyl)-6-methoxy-1H-indole-3-carbaldehyde, C17H12INO3
  47. Crystal structure of bis(acridinium) tetrabromidomanganate(II), C26H20Br4MnN2
  48. The crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene)) bis(2-(tert-butyl)phenol), C22H28N2O2
  49. The crystal structure of the cocrystal di-μ2-chlorido-tetramethyl-tetraphenyl-di-μ3-oxido-dichloridotetratin(IV) – diphenyl-methyl-chloridotin(IV)(1/2), C54H58Cl6O2Sn6
  50. Crystal structure of (3a7R,13bR)-3-((1R)-1-hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3a,11,11,13b-tetramethyl-2,3,3a,4,5,11,11a,12,13,13b-decahydroindeno[5′,4′:4,5] cyclohepta[1,2-c]oxepin-9(1H)-one, C30H40O5
  51. Crystal structure of 1-(4-methoxyphenyl)-2-phenoxyethan-1-one, C15H14O3
  52. Crystal structure of trans-tetrakis(3-phenylpyridine-κN)bis(thiocyanato-κN)nickel(II), C46H36N6NiS2
  53. Crystal structure of sodium catena-poly[bis(thiourea-κ1S)-tetrakis(μ2-thiourea-κ2S,S)tricopper(I)] difumarate, C14H29Cu3N12NaO8S6
  54. Crystal structure of bis(benzylamine-κ1N)-bis((E)-2-methyl-3-phenylacrylato-κ1O)copper(II), C34H36CuN2O4
  55. The crystal structure of 3,4-dihydroxybenzoic acid – 3-[7-{[2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3] triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol – water (1/1/1), C30H36F2N6O9S
  56. Crystal structure of catena-poly[dipyridine-bis(pyridine-2-carboxylato-κ 2 N,O)-bis(μ 2-pyridine-2-carboxylato-κ 2 N,O)-dinickel(II)], C34H26N6Ni2O8
  57. The crystal structure of 1-((1-methyl-1H-1,2,4-triazol-3-yl) methyl)-3-(2,4,5-trifluorobenzyl)-1,3,5-triazinane-2,4,6-trione, C14H11F3N6O3
  58. Crystal structure of (E)-2-((Z)-2-((1S,4R)-3,3-dimethylbicyclo[2.2.1] heptan-2-ylidene)ethylidene)hydrazine-1-carbothioamide, C24H38N6S2
  59. Crystal structure of photochromic 3-(5-(2,5-dimethylthiophen-3-yl)-2,2,3,3,4,4-hexafluorocyclopentyl)-2-methylbenzo[b]-thiophene, C20H14F6S2
  60. Crystal structure of bis(2,5,5,7-tetramethyl-1,4-diazepane-1,4-diium) diaqua-bis(1,2-diaminopropane)copper(II) bis(μ6-oxido)tetrakis(μ3-oxido)-tetradecakis(μ2-oxido)-octaoxido-decavanadium(V) – water (1/4), C24H76CuN8V10O34
  61. Crystal structure of 1,2,3,5,13-pentamethoxy-6,7-dimethyl-1,2,3,4,4a,5,6,7,8,13b-decahydrobenzo[3′,4′]cycloocta[1′,2′:4,5]benzo[1,2-d][1,3]dioxole, C24H30O7
  62. Crystal structure of bis(6-carboxyhexyl)-4,4′-bipyridinium dibromide – 2,6-dihydroxynaphthalene (1/2), C42H46Br2N2O8
  63. Crystal structure of methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H21ClN2O5
  64. Crystal structure of bis(dimethylammonium) poly[{μ4-1,1ʹ-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato)-κ6N4O2}zinc(II)], C22H26N6O8Zn
  65. Crystal structure of 2-(2-(4-methoxyphenyl)-2H-indazol-3-yl)acetonitrile, C16H13N3O
  66. Crystal structure of (E)-7-methoxy-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23NO3
  67. The crystal structure of N′1,N′2-bis((E)-3-(tert-butyl)-2-hydroxybenzylidene)oxalohydrazide, C24H30N4O4
  68. The crystal structure of trimethyl 2,2′,2′′-(benzene-1,3,5-triyltris(oxy))triacetate, C15H18O9
  69. Crystal structure of bis(N,N-dimethylformamide-κO)-bis(pyridine-2-carboxylato-κ2N,O)-bis(μ2-pyridine-2-carboxylato-κ2N,O)-dinickel(II), C30H30N6Ni2O10
  70. Crystal structure of bis(μ2-1-pyrenecarboxylato-κ3O,O′:O′)-bis(1-pyrenecarboxylato-κ2O,O′)-(benzimidazole-κ1N)dicadmium(II), C82H48Cd2N4O8
  71. One-pot synthesis and crystal structure of diethyl 2,6-dimethyl-4-(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate, C21H23N5O6
  72. The crystal structure of 1-(2-fluorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carbonitrile, C18H13FN2O2
  73. Crystal structure of bis(trimethylphenylammonium) aqua-oxido-octathiotritungstate, (Me3PhN)2[W3OS8(H2O)]
  74. The crystal structure of trichlorido[N-[(2-oxyphenyl)methylidene]phenylglycinemethylester-κ3O,N,O′]-tin(IV) – methylene chloride (1/1), C16H14Cl3NO3Sn·CH2Cl2
  75. The crystal structure of furan-2,5-diylbis((4-chlorophenyl)methanol), C18H14Cl2O3
  76. The crystal structure of hexalithium decavanadate hexadecahydrate, H32Li6O44V10
  77. Crystal structure of ethyl 4-{[5-(adamantan-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,4-oxadiazol-3-yl]methyl}piperazine-1-carboxylate, C20H30N4O3S
  78. Crystal structure of aqua(μ2-2,2′,2″-((nitrilo)tris(ethane-2,1-diyl(nitrilo)methylylidene))tris (6-ethoxyphenolato))(pentane-2,4-dionato-κ2O,O′)-dinickel(II), C38H48N4Ni2O9
https://doi.org/10.1515/ncrs-2022-0536
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Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of methyl 2-((4-chloro-2-fluoro-6-((2,2,2-trifluoroethyl) thio)phenoxy)methyl)benzoate, C17H13ClF4O3S
  4. The crystal structure of 3-hydroxy-5-oxo-4-propanoylcyclohex-3-ene-1-carboxylic monohydrate, C10H14O6
  5. Crystal structure of 2-({[5-(adamantan-2-yl)-2-sulfanylidene-1,3,4-oxadiazolidin-3-yl]methyl}amino)benzonitrile, C20H22N4OS
  6. Crystal structure of 1-(3-bromopropyl)-2-((4-chlorophenoxy)methyl)-4-methyl-1H-benzo[d]imidazole, C18H18BrClN2O
  7. Crystal structure of 2-methoxy-6-[(2-morpholin-4-yl-phenylamino)-methylene]-4-nitro-cyclohexa-2,4-dienone, C18H19N3O5
  8. The crystal structure of 2-(7-(2,3-dimethoxyphenyl)-[1,2,4]triazolo[1,5-a]-pyrimidin-5-yl)-3-methoxyphenol, C20H18N4O4
  9. The crystal structure of 3-(1-(2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazinyl)ethylidene)chroman-2,4-dione dihydrate, C20H22N2O8
  10. Crystal structure of 3,5,7-trimethoxy-3′,4′-methylenedioxy-flavone, C19H16O7
  11. The crystal structure of strictic acid, C20H26O3
  12. Crystal structure of 1,1′-(pyrazine-1,4-diyl)-bis(propan-2-one), C10H14N2O2
  13. The crystal structure of 1-(adamantan-1-yl)-3-(4-chlorophenyl)urea, C17H21ClN2O
  14. The crystal structure of (2R,6′R)-2′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-2′-ene-3,4′-dione, C16H14Cl2O5
  15. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-3-((4-methoxyphenyl)amino)-10,13-dimethylhexadecahydro-1H-cyclopenta[α]-phenanthren-17-yl)ethan-1-one, C28H41NO2
  16. Crystal structure of N-2,6-difluorobenzoyl-N′-[1-(3-chloro-4-methyl-phenyl)-4-cyano-1H-pyrazol-5-carbamoyl]urea, C19H12ClF2N5O2
  17. Crystal structure of (−)-β-D-19-glucopiranosyl-9,15-dihydroxy kaurenoate, C26H40O9
  18. Crystal structure of 7-hydroxy-6-(2-hydroxyethyl)-2H-chromen-2-one, C11H10O4
  19. Crystal structure of S-(benzo[d]thiazol-2-yl)-N-(tert-butyl)thiohydroxylamine, C11H14N2S2
  20. Crystal structure of poly[di-µ2-aqua-aqua-nitrato-κ2O,O′-(µ3-2-nitroisophthalato-κ4O,O′:O″:O′″)barium(II)natrium(II)] monohydrate, C8H11BaN2NaO13
  21. The crystal structure of diaqua-bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2 N,O)-cobalt(II) dihydrate, C14H16N6O8Co
  22. Crystal structure of (S,E)-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-4-yl)-2,3- dihydroquinazolin-4(1H)-one monohydrate, C19H15N5O⋅H2O
  23. Synthesis and crystal structure of 5-(8-(((5-carboxypentyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxy-3-nitrobenzenesulfonate monohydrate, C22H24N2O12S
  24. Synthesis and crystal structure of 8-bromo-3-(1H-pyrazole-1-carbonyl)-2H-chromen-2-one, C13H7BrN2O3
  25. Crystal structure of E-7-fluoro-2-(4-methoxy-3-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  26. Hydrogen bonded dimers in the crystal structure of 2-chloro-N-((3,5-dimethylphenyl)carbamoyl)-nicotinamide, C30H28Cl2N6O4
  27. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-allyl-1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C10H12F6N2P
  28. Crystal structure of (E)-7-bromo-2-(4-(4-methylpiperazin-1-yl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23BrN2O
  29. Crystal structure of pentacarbonyl-(μ2-ethane-1,2-dithiolato-κ4S:S,S′:S′)-(diphenyl(o-tolyl)phosphine-κ1P)diiron (Fe–Fe), C26H21Fe2O5PS2
  30. Crystal structure of 9-(2-chloroethoxy)-4-(4-methoxy-3-(trifluoromethyl)phenyl)- 5,6-dihydrobenzo[h]quinazolin-2-amine, C22H19ClF3N3O2
  31. Crystal structure of triaqua-[5-bromo-2-(carboxylatomethoxy)benzoate-κ3 O,O′,O″]nickel(II), C9H11BrNiO8
  32. The crystal structure of 4,4′-dichloro-3,5′-diphenyl-1′H-1,3′- bipyrazole, C18H12Cl2N4
  33. The crystal structure of bis(1H-pyrazole-carboxamidine-κN,N′)bis(nitrato-κO)-copper(II), C8H12CuN10O6
  34. Synthesis and crystal structure of 3-bromo-4-phenyl-2H-chromene, C15H11BrO
  35. Crystal structure of (E)-5-(diethylamino)-2-((morpholinoimino)methyl)phenol, C15H23N3O2
  36. Crystal structure of niobium trigallide, NbGa3
  37. Crystal structure of dimethyl 4,4′-(((1R, 2R)-cyclohexane-1,2-diyl)bis(azanediyl))dibenzoate, C22H26N2O4
  38. Crystal structure of dimethyl 4,4′-((4R, 5R)-4,5-diphenylimidazolidine-1,3-diyl)dibenzoate, C31H28N2O4
  39. The crystal structure of 2-(2-bromophenyl)-4-phenylbenzo[b][1,4]oxaphosphinine 4-oxide, C20H14BrO2P
  40. The crystal structure of 3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one, C18H21NO4
  41. Crystal structure of catena-poly[[μ2-1,3-bis[(1H-imidazol-1- yl)methyl]benzene-N:N′]-(μ2–D–camphorato-O, O′: O″, O‴)cadmium(II)], C48H56Cd2N8O8
  42. Crystal structure of N-(4-bromophenyl)-4-[3-(trifluoromethyl)phenyl]-piperazine-1-carbothioamide, C18H17BrF3N3S
  43. The crystal structure of cis-Dicyano-bis(2,2′-bipyridine)k2N,N′-chromium(III) hexafluorophosphate, C22H16N6F6PCr
  44. Crystal structure of 4-((6-bromohexyl)oxy)-2-hydroxybenzaldehyde, C13H17BrO3
  45. Crystal structure of hydrazinium methanesulfonate, CH8N2O3S
  46. Crystal structure of 1-(2-iodobenzoyl)-6-methoxy-1H-indole-3-carbaldehyde, C17H12INO3
  47. Crystal structure of bis(acridinium) tetrabromidomanganate(II), C26H20Br4MnN2
  48. The crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene)) bis(2-(tert-butyl)phenol), C22H28N2O2
  49. The crystal structure of the cocrystal di-μ2-chlorido-tetramethyl-tetraphenyl-di-μ3-oxido-dichloridotetratin(IV) – diphenyl-methyl-chloridotin(IV)(1/2), C54H58Cl6O2Sn6
  50. Crystal structure of (3a7R,13bR)-3-((1R)-1-hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3a,11,11,13b-tetramethyl-2,3,3a,4,5,11,11a,12,13,13b-decahydroindeno[5′,4′:4,5] cyclohepta[1,2-c]oxepin-9(1H)-one, C30H40O5
  51. Crystal structure of 1-(4-methoxyphenyl)-2-phenoxyethan-1-one, C15H14O3
  52. Crystal structure of trans-tetrakis(3-phenylpyridine-κN)bis(thiocyanato-κN)nickel(II), C46H36N6NiS2
  53. Crystal structure of sodium catena-poly[bis(thiourea-κ1S)-tetrakis(μ2-thiourea-κ2S,S)tricopper(I)] difumarate, C14H29Cu3N12NaO8S6
  54. Crystal structure of bis(benzylamine-κ1N)-bis((E)-2-methyl-3-phenylacrylato-κ1O)copper(II), C34H36CuN2O4
  55. The crystal structure of 3,4-dihydroxybenzoic acid – 3-[7-{[2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3] triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol – water (1/1/1), C30H36F2N6O9S
  56. Crystal structure of catena-poly[dipyridine-bis(pyridine-2-carboxylato-κ 2 N,O)-bis(μ 2-pyridine-2-carboxylato-κ 2 N,O)-dinickel(II)], C34H26N6Ni2O8
  57. The crystal structure of 1-((1-methyl-1H-1,2,4-triazol-3-yl) methyl)-3-(2,4,5-trifluorobenzyl)-1,3,5-triazinane-2,4,6-trione, C14H11F3N6O3
  58. Crystal structure of (E)-2-((Z)-2-((1S,4R)-3,3-dimethylbicyclo[2.2.1] heptan-2-ylidene)ethylidene)hydrazine-1-carbothioamide, C24H38N6S2
  59. Crystal structure of photochromic 3-(5-(2,5-dimethylthiophen-3-yl)-2,2,3,3,4,4-hexafluorocyclopentyl)-2-methylbenzo[b]-thiophene, C20H14F6S2
  60. Crystal structure of bis(2,5,5,7-tetramethyl-1,4-diazepane-1,4-diium) diaqua-bis(1,2-diaminopropane)copper(II) bis(μ6-oxido)tetrakis(μ3-oxido)-tetradecakis(μ2-oxido)-octaoxido-decavanadium(V) – water (1/4), C24H76CuN8V10O34
  61. Crystal structure of 1,2,3,5,13-pentamethoxy-6,7-dimethyl-1,2,3,4,4a,5,6,7,8,13b-decahydrobenzo[3′,4′]cycloocta[1′,2′:4,5]benzo[1,2-d][1,3]dioxole, C24H30O7
  62. Crystal structure of bis(6-carboxyhexyl)-4,4′-bipyridinium dibromide – 2,6-dihydroxynaphthalene (1/2), C42H46Br2N2O8
  63. Crystal structure of methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H21ClN2O5
  64. Crystal structure of bis(dimethylammonium) poly[{μ4-1,1ʹ-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato)-κ6N4O2}zinc(II)], C22H26N6O8Zn
  65. Crystal structure of 2-(2-(4-methoxyphenyl)-2H-indazol-3-yl)acetonitrile, C16H13N3O
  66. Crystal structure of (E)-7-methoxy-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23NO3
  67. The crystal structure of N′1,N′2-bis((E)-3-(tert-butyl)-2-hydroxybenzylidene)oxalohydrazide, C24H30N4O4
  68. The crystal structure of trimethyl 2,2′,2′′-(benzene-1,3,5-triyltris(oxy))triacetate, C15H18O9
  69. Crystal structure of bis(N,N-dimethylformamide-κO)-bis(pyridine-2-carboxylato-κ2N,O)-bis(μ2-pyridine-2-carboxylato-κ2N,O)-dinickel(II), C30H30N6Ni2O10
  70. Crystal structure of bis(μ2-1-pyrenecarboxylato-κ3O,O′:O′)-bis(1-pyrenecarboxylato-κ2O,O′)-(benzimidazole-κ1N)dicadmium(II), C82H48Cd2N4O8
  71. One-pot synthesis and crystal structure of diethyl 2,6-dimethyl-4-(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate, C21H23N5O6
  72. The crystal structure of 1-(2-fluorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carbonitrile, C18H13FN2O2
  73. Crystal structure of bis(trimethylphenylammonium) aqua-oxido-octathiotritungstate, (Me3PhN)2[W3OS8(H2O)]
  74. The crystal structure of trichlorido[N-[(2-oxyphenyl)methylidene]phenylglycinemethylester-κ3O,N,O′]-tin(IV) – methylene chloride (1/1), C16H14Cl3NO3Sn·CH2Cl2
  75. The crystal structure of furan-2,5-diylbis((4-chlorophenyl)methanol), C18H14Cl2O3
  76. The crystal structure of hexalithium decavanadate hexadecahydrate, H32Li6O44V10
  77. Crystal structure of ethyl 4-{[5-(adamantan-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,4-oxadiazol-3-yl]methyl}piperazine-1-carboxylate, C20H30N4O3S
  78. Crystal structure of aqua(μ2-2,2′,2″-((nitrilo)tris(ethane-2,1-diyl(nitrilo)methylylidene))tris (6-ethoxyphenolato))(pentane-2,4-dionato-κ2O,O′)-dinickel(II), C38H48N4Ni2O9
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Heruntergeladen am 16.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2022-0536/html?lang=de
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