Home The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
Article Open Access

The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2

  • Nikolay T. Tzvetkov ORCID logo EMAIL logo , Martina I. Peeva , Ivanka Tsakovska ORCID logo , Luigi Milella ORCID logo , Ilza Pajeva ORCID logo and Hans-Georg Stammler
Published/Copyright: February 21, 2022
Download Article (PDF)
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 2

Abstract

C15H16Cl2N4O2, monoclinic, P21/c (no. 14), a = 26.2014(7) Å, b = 7.59320(10) Å, c = 17.9766(4) Å, β = 109.217(3)°, V = 3377.20(14) Å3, Z = 8, R gt (F) = 0.0503, wR ref (F 2) = 0.1411, T = 100.0(1) K.

CCDC no.: 2150471

The asymmetric unit of the title crystal 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: Colorless plate
Size: 0.17 × 0.07 × 0.02 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 3.59 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 76.4°, >99%
N(hkl)measured, N(hkl)unique, R int: 51,349, 8782, 0.044
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 7282
N(param)refined: 441
Programs: CrysAlisPRO [1], Olex2 [2], SHELX [3, 4]
Table 2:

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

Atom x y z U iso*/U eq
Cl1a 0.24064 (6) 0.8803 (2) 0.54017 (9) 0.0601 (4)
Cl2 0.20413 (4) 0.90910 (16) 0.34773 (7) 0.0618 (3)
Cl3b 0.28647 (10) 0.7416 (4) 0.25871 (12) 0.0443 (7)
O1 0.44535 (10) 0.0447 (3) 0.86184 (11) 0.0312 (4)
O2 0.44157 (10) 0.6376 (2) 0.70472 (12) 0.0339 (5)
N1 0.42112 (10) 0.0409 (3) 0.65427 (12) 0.0232 (4)
N2 0.42767 (10) −0.0051 (3) 0.73251 (12) 0.0230 (4)
H2 0.424750 −0.117917 0.741555 0.028*
N3 0.42918 (9) 0.3351 (3) 0.69885 (11) 0.0197 (4)
N4 0.42162 (9) 0.4782 (3) 0.58863 (12) 0.0207 (4)
C1 0.43787 (12) 0.1021 (3) 0.79549 (15) 0.0233 (5)
C2 0.44052 (15) 0.3005 (3) 0.78324 (15) 0.0312 (6)
H2A 0.478422 0.339455 0.811589 0.037*
C3 0.42210 (10) 0.2057 (3) 0.64346 (13) 0.0190 (5)
C5 0.4042 (2) 0.3985 (5) 0.8177 (2) 0.0532 (11)
H5A 0.405546 0.524576 0.806851 0.080*
H5B 0.416149 0.379461 0.874826 0.080*
H5C 0.367050 0.355768 0.794188 0.080*
C6 0.43151 (11) 0.4997 (3) 0.66679 (14) 0.0223 (5)
C7 0.41816 (11) 0.2906 (3) 0.56517 (14) 0.0206 (5)
C8 0.46718 (12) 0.2348 (4) 0.54158 (15) 0.0257 (5)
H8A 0.466340 0.296842 0.493392 0.039*
H8B 0.465855 0.107456 0.532216 0.039*
H8C 0.500565 0.264517 0.584107 0.039*
C9 0.36532 (12) 0.2479 (4) 0.50024 (16) 0.0289 (6)
H9A 0.334832 0.285889 0.516487 0.043*
H9B 0.362981 0.120590 0.490631 0.043*
H9C 0.364153 0.309595 0.451837 0.043*
C10 0.42311 (11) 0.6247 (3) 0.53679 (15) 0.0241 (5)
H10A 0.441900 0.585872 0.500031 0.029*
H10B 0.444481 0.721855 0.569064 0.029*
C11 0.36803 (11) 0.6939 (3) 0.48958 (15) 0.0229 (5)
C12 0.33246 (12) 0.7516 (4) 0.52757 (16) 0.0273 (5)
H12 0.342715 0.745747 0.583353 0.033*
C13 0.28240 (13) 0.8172 (4) 0.4842 (2) 0.0356 (6)
H13b 0.258358 0.857075 0.510283 0.043*
C14 0.26701 (13) 0.8252 (4) 0.4026 (2) 0.0387 (7)
C15 0.30212 (14) 0.7692 (6) 0.36474 (19) 0.0434 (8)
H15a 0.291907 0.776254 0.308987 0.052*
C16 0.35204 (13) 0.7031 (4) 0.40802 (17) 0.0331 (6)
H16 0.375880 0.663203 0.381616 0.040*
Cl21a 0.20841 (6) 0.1885 (3) −0.03351 (8) 0.0585 (4)
Cl22 0.29098 (4) 0.0819 (2) 0.13548 (7) 0.0710 (3)
Cl24b 0.27097 (9) 0.2646 (4) 0.29263 (13) 0.0441 (7)
O21 0.05460 (9) 0.9722 (2) 0.41383 (11) 0.0274 (4)
O22 0.05551 (9) 0.3798 (2) 0.26042 (11) 0.0276 (4)
N21 0.07745 (9) 0.9750 (3) 0.22835 (12) 0.0200 (4)
N22 0.07060 (9) 1.0221 (3) 0.30005 (12) 0.0196 (4)
H22 0.071980 1.135487 0.310705 0.024*
N23 0.06836 (9) 0.6815 (2) 0.26527 (12) 0.0187 (4)
N24 0.07511 (9) 0.5362 (3) 0.16239 (12) 0.0208 (4)
C21 0.06214 (10) 0.9141 (3) 0.35464 (13) 0.0194 (5)
C22 0.06107 (12) 0.7159 (3) 0.34149 (14) 0.0241 (5)
H22A 0.024752 0.670534 0.339216 0.029*
C23 0.07601 (10) 0.8096 (3) 0.21674 (13) 0.0178 (4)
C25 0.10347 (15) 0.6249 (4) 0.40855 (17) 0.0362 (7)
H25A 0.101788 0.497557 0.399094 0.054*
H25B 0.096774 0.649356 0.458058 0.054*
H25C 0.139361 0.668682 0.411983 0.054*
C26 0.06558 (11) 0.5152 (3) 0.23124 (14) 0.0199 (5)
C27 0.08086 (11) 0.7232 (3) 0.14327 (14) 0.0210 (5)
C28 0.03465 (12) 0.7830 (3) 0.07122 (14) 0.0262 (5)
H28A 0.037428 0.724005 0.024214 0.039*
H28B 0.036674 0.910765 0.065095 0.039*
H28C 0.000080 0.752614 0.077968 0.039*
C29 0.13579 (12) 0.7594 (4) 0.13373 (16) 0.0274 (5)
H29A 0.164632 0.720584 0.181144 0.041*
H29B 0.139521 0.885887 0.126022 0.041*
H29C 0.138408 0.694855 0.087914 0.041*
C30 0.07418 (11) 0.3899 (3) 0.10984 (14) 0.0221 (5)
H30A 0.056105 0.428730 0.054858 0.026*
H30B 0.052269 0.293496 0.120934 0.026*
C31 0.12956 (11) 0.3184 (3) 0.11694 (15) 0.0216 (5)
C32 0.14193 (13) 0.2777 (4) 0.05010 (18) 0.0342 (6)
H32 0.116201 0.300355 −0.000279 0.041*
C33 0.19119 (14) 0.2046 (5) 0.0555 (2) 0.0432 (8)
H33b 0.198910 0.174851 0.008941 0.052*
C34 0.22937 (13) 0.1745 (5) 0.1285 (2) 0.0385 (7)
C35 0.21756 (15) 0.2155 (7) 0.1953 (2) 0.0534 (10)
H35a 0.243745 0.195419 0.245533 0.064*
C36 0.16758 (13) 0.2861 (6) 0.18997 (19) 0.0429 (8)
H36 0.159494 0.312315 0.236556 0.052*

  1. aOccupancy: 0.670 (2), bOccupancy: 0.330 (2).

Source of material

The title compound has been obtained via a five-step synthetic procedure using an intramolecular N1–C5 heterocondensation of [3-(3,4-dichlorobenzyl)-4,4-dimethyl-2-oxo-5-thioxoimidazolidin-1-yl]propionic acid ethyl ester with a large excess of hydrazine hydrate (20 equiv.) in dry ethanol as last step [5]. The mixture was stirred under reflux for then hours in the presence of freshly activated molecular sieve 4 Å under argon atmosphere. In a typical condensation reaction 10.0 mg molecular sieve was used for the conversion of 1.00 mmol starting material. After evaporation, the crude product was purified by column chromatography on silica gel (dichloromethane/methanol, 95:5, R f  = 0.49) followed by RP-HPLC (methanol/water, 70:30) to give a pure product as a white solid. Colorless flaky-like crystals suitable for X-ray structure analysis were obtained after recrystallization from methanol and crystallization over a period of several days at 268–270 K (m.p. 468–469 K).

Experimental details

A single crystal of the title compound was examined on a Rigaku Supernova diffractometer [1] using Cu-Ka (λ = 1.54184 Å) radiation. The crystal was kept at 100.0(1) K during data collection. Using Olex2 [2], the structure was solved with the ShelXT [3] structure solution program using Intrinsic Phasing and refined with the ShelXL [4] refinement package using Least Squares minimization. Positional disorder of one chlorine atom with ratio 67:33 can be obtained at each of the two molecules inside the asymmetric unit, which is shown in the figure. Displacement ellipsoids are drawn at the 50% probability level, only the major occupied part of the disorder is shown. Hydrogen atoms were taken into account using a riding model. The crystal was pseudomerohedrically twinned with ratio 65:35, transformation matrix: 1.0000 0.0003 −0.0000 0.0000 −0.9999 0.0000 −0.9618 −0.0003 −1.0001.

Comment

The title structure was prepared following our previous procedure for regioselective synthesis of drug-like small molecules incorporating an imidazo[1,2,4]triazine-3,6-dione framework [5, 6]. There are several biologically active compounds and natural products comprising a condensed heterobicyclic 1,2,4-triazine scaffold [7]. The large variety of biological effects include antimicrobial [8], antiinflammatory [9], neuroprotective [10], and anticancer [11] properties. The racemic compound crystallizes centrosymmetrically and the asymmetric unit contains two independent molecules, which show different orientation of the chlorine atoms Cl1 and Cl3 (for molecule No. 1) and Cl21 and Cl23 (for molecule No. 2), respectively, in position meta of the benzyl moiety. Both molecules showed positional disorder of the chlorine atoms around the C10–C11 and C30–C31 bonds, representing a rotameric mixture in a 2:1 ratio. The crystal structure contains eight molecules per unit cell. The enantiomeric molecules show an antiparallel orientation in the crystal packing. All intramolecular bond lengths are normal. The significant shorter N1–N2 (1.404(3) Å) and N21–N22 (1.405(3) Å) bonds indicate the localization of the double bond of the corresponding six-membered rings. The imidazo[1,2,4] trazine unit in all molecules is almost planar. The methyl group is connected to the imidazotriazine basic structure in the corresponding asymmetric centers C2 and C21 and it is cis to the benzyl substituent in the positions N4 and N24 of the respective molecule No. 1 and No. 2. The main imidazotriazine core in both molecules is almost planar including followed atoms for molecule No. 1: N1, N2, N3, N4, C1, C2, C3, C6, C7, C10, O1, O2, and for molecule No. 2: N21, N22, N23, N24, C21, C22, C23, C26, C27, C30, O21, O22. The benzyl substituent forms a second planar moiety consisting of C10, C11, C12, C13, C14, C15, C16 for molecule No. 1, and C30, C31, C32, C33, C34, C35, C36 for molecule No. 2. The tilt angle between the main imidazotriazine planes and the second planar arrangement are 71.7(0)° for molecule No. 1 and 75.0(2)° for molecule No. 2. The benzyl and the imidazotriazine moiety form a bond angle of N4–C10–C11 = 113.8(2)° for molecule No. 1 and N24–C30–C31 = 114.1(2)° for molecule No. 2, respectively.

Corresponding author: Nikolay T. Tzvetkov, Institute of Molecular Biology, “Roumen Tsanev”, Bulgarian Academy of Sciences, Acad. G. Bonchev Str., Bl. 21, Sofia 1113, Bulgaria, E-mail:

Funding source: Bulgarian National Science Fund

Award Identifier / Grant number: KP-06-OPR 03/8

  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 financially supported by the Bulgarian National Science Fund (No. KP-06-OPR 03/8).

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

References

1. Rigaku Oxford Diffraction CrysAlisPro (Rigaku, V1.171.41.104a), 2021.Search in Google Scholar

2. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

3. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.Search in Google Scholar PubMed

4. Sheldrick, G. M. SHELXTL – Integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Search in Google Scholar PubMed PubMed Central

5. Tzvetkov, N. T., Euler, H., Müller, C. E. Regioselective synthesis of 7,8-dihydroimidazo[5,1c ][1,2,4]triazine-3,6(2H,4H)-dione derivatives: a new drug-like heterocyclic scaffold. Beilstein J. Org. Chem. 2012, 8, 1584–1593; https://doi.org/10.3762/bjoc.8.181.Search in Google Scholar PubMed PubMed Central

6. Tzvetkov, N. T., Neumann, B., Stammler, H.-G. The twinned crystal structure of (4SR)-7-benzyl-2,4,8,8-tetramethyl-7,8-dihydroimidazo [5,1c] [1,2,4]triazine-3,6(2H,4H)-dione, C16H20N4O2. Z. Kristallogr. N.Cryst. Struct. 2017, 232, 231–233; https://doi.org/10.1515/ncrs-2016-0218.Search in Google Scholar

7. Maechling, S., Good, J., Lindell, S. D. Synthesis of a solid-phase amino imidazotriazine library via palladium catalyzed direct arylation. J. Comb. Chem. 2012, 12, 818–821; https://doi.org/10.1021/cc1001617.Search in Google Scholar PubMed

8. Sztanke, K., Pasternak, K., Rajtar, B., Sztanke, M., Majek, M., Polz-Dacewicz, M. Identification of antibacterial and antiviral activities of novel fused 1,2,4-triazine esters. Bioorg. Med. Chem. 2007, 15, 5480–5486; https://doi.org/10.1016/j.bmc.2007.05.048.Search in Google Scholar PubMed

9. Oku, T., Kawai, Y., Marusawa, H., Tanaka, H. Imidazotriazine derivatives. WO Patent 92/12154, 1992.Search in Google Scholar

10. Siegel, S., Wilmen, A., Röhrig, S., Svenstrup, N., Gnoth, M. J., Heitmeier, S., Rester, U., Pyrazolopyrazine and Imidazotriazine und ihre Verwendung. DE Patent 10 2007 032 349A1, 2009.Search in Google Scholar

11. Sztanke, K., Pasternak, K., Rzymowska, J., Sztanke, M., Kandefer-Szerszeǹ, M. Synthesis, structure elucidation and identification of antitumoral properties of novel fused 1,2,4-triazine aryl derivatives. Eur. J. Med. Chem. 2008, 43, 1085–1094; https://doi.org/10.1016/j.ejmech.2007.07.009.Search in Google Scholar PubMed

Received: 2022-01-14
Accepted: 2022-02-07
Published Online: 2022-02-21
Published in Print: 2022-04-26

© 2022 Nikolay T. Tzvetkov et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
  22. The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
  23. The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
  25. Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
  40. Crystal structure of a second modification of Pachypodol, C18H16O7
  41. Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
  42. The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
  44. The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
  45. Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
  46. The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
  47. Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
https://doi.org/10.1515/ncrs-2022-0016
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
  22. The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
  23. The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
  25. Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
  40. Crystal structure of a second modification of Pachypodol, C18H16O7
  41. Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
  42. The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
  44. The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
  45. Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
  46. The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
  47. Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 21.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2022-0016/html
Scroll to top button