Home Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
Article Open Access

Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S

  • Lamya H. Al-Wahaibi , Olivier Blacque , Nora H. Al-Shaalan , Edward R. T. Tiekink and Ali A. El-Emam ORCID logo EMAIL logo
Published/Copyright: October 28, 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 238 Issue 1

Abstract

C14H18F3N3S, monoclinic, P21/c (no. 14), a = 4.61919(4) Å, b = 29.1507(3) Å, c = 11.27803(10) Å, β = 94.4768(8)°, V = 1513.99(3) Å3, Z = 4, R gt (F) = 0.0588, wR ref (F 2) = 0.1579, T = 160 K.

CCDC no.: 2211988

The molecular structure and supramolecular chain in the crystal are shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Plate, colourless
Size: 0.19 × 0.06 × 0.03 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 2.18 mm−1
Diffractometer, scan mode: SuperNova, ω-scans
θ max, completeness: 74.5°, >99%
N(hkl)measured, N(hkl)unique, R int: 15,788, 3093, 0.016
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2960
N(param)refined: 223
Programmes: CrysAlis Pro [1], SHELX [2, 3], OLEX2 [4]
Table 2:

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

x y z U iso*/U eq
F1Aa 0.4357 (7) 0.58429 (9) 0.6886 (3) 0.0474 (5)
F1Bb 0.3499 (13) 0.58397 (15) 0.7181 (5) 0.0486 (6)
F2Aa 0.2987 (8) 0.54297 (12) 0.5417 (2) 0.0476 (5)
F2Bb 0.3990 (13) 0.5475 (2) 0.5534 (4) 0.0470 (6)
F3Aa 0.0078 (6) 0.55534 (12) 0.6761 (3) 0.0490 (5)
F3Bb −0.0038 (7) 0.5406 (2) 0.6326 (6) 0.0480 (6)
N1 −0.0072 (5) 0.22093 (7) 0.65401 (18) 0.0303 (4)
H1 0.030 (7) 0.2288 (11) 0.724 (3) 0.036 (8)*
N2 0.1803 (4) 0.28986 (6) 0.59848 (16) 0.0259 (4)
N3 0.3860 (4) 0.37736 (6) 0.68388 (16) 0.0255 (4)
S1 −0.14082 (13) 0.24423 (2) 0.42956 (5) 0.0308 (2)
C1 0.0077 (8) 0.13887 (10) 0.6014 (3) 0.0518 (8)
H1A 0.091089 0.146572 0.526609 0.078*
H1B −0.114146 0.111468 0.589903 0.078*
H1C 0.164508 0.132875 0.663057 0.078*
C2 −0.1743 (6) 0.17842 (9) 0.6392 (2) 0.0397 (6)
H2A −0.338581 0.183240 0.578665 0.048*
H2B −0.255863 0.170638 0.715243 0.048*
C3 0.0232 (5) 0.25208 (7) 0.56815 (19) 0.0235 (4)
C4 0.2233 (6) 0.32746 (8) 0.51589 (19) 0.0296 (5)
H4A 0.080032 0.324900 0.446205 0.036*
H4B 0.420077 0.325286 0.487260 0.036*
C5 0.1886 (5) 0.37352 (8) 0.57601 (19) 0.0272 (5)
H5A 0.230083 0.398459 0.520192 0.033*
H5B −0.014348 0.377036 0.596975 0.033*
C6 0.3377 (5) 0.33956 (8) 0.76581 (19) 0.0273 (5)
H6A 0.138233 0.341476 0.791780 0.033*
H6B 0.475838 0.342147 0.837163 0.033*
C7 0.3790 (5) 0.29401 (8) 0.7059 (2) 0.0276 (5)
H7A 0.582014 0.291312 0.684401 0.033*
H7B 0.341862 0.268811 0.761588 0.033*
C8 0.4369 (5) 0.42106 (8) 0.7331 (2) 0.0263 (5)
C9 0.3234 (5) 0.46090 (8) 0.6790 (2) 0.0285 (5)
H9 0.193717 0.458766 0.609566 0.034*
C10 0.3992 (5) 0.50383 (8) 0.7263 (2) 0.0322 (5)
C11 0.5772 (7) 0.50860 (9) 0.8290 (2) 0.0422 (6)
H11 0.623244 0.538034 0.861293 0.051*
C12 0.6876 (7) 0.46900 (10) 0.8840 (3) 0.0488 (7)
H12 0.810089 0.471421 0.955373 0.059*
C13 0.6226 (6) 0.42604 (9) 0.8367 (2) 0.0384 (6)
H13 0.704986 0.399548 0.875030 0.046*
C14 0.2839 (5) 0.54539 (9) 0.6596 (2) 0.0442 (5)

  1. Occupancies: a0.642 (5), b0.358 (5).

Source of material

Ethyl isothiocyanate (436 mg, 5.0 mmol) was added to a solution of 1-(3-trifluoromethylphenyl)piperazine (1.15 g, 5.0 mmol) in ethanol (8 mL), and the mixture was heated under reflux for 1 h. Water (15 mL) was added and the mixture was stirred for further 30 min at room temperature. The precipitated crude product was filtered, washed with water, dried and crystallised from aqueous ethanol to yield 1.49 g (94%) of the title compound (I) as colourless plates. M.pt: 380–381 K (uncorrected). 1H NMR (CDCl3, 500.13 MHz): δ 1.30 (t, 3H, CH3, J = 7.5 Hz), 3.26–3.28 (m, 4H, Piperazine–H), 3.96 (t, 4H, Piperazine–H, J = 7.0 Hz), 4.40 (q, 2H, CH3, J = 7.5 Hz), 6.88–6.89 (m, 1H, Ar–H), 7.26–7.42 (m, 4H, Ar–H & NH). 13C NMR (CDCl3, 125.76 MHz): δ 14.66 (CH3), 39.98 (CH2), 52.50, 54.82 (Piperazine–C), 112.06, 114.20, 119.62, 130.76, 132.25, 150.14 (Ar–C), 124.86 (CF3), 179.84 (C=S). ESI–MS, m/z: 318.4 [M+H]+.

Experimental details

The C-bound H atoms were geometrically placed (C–H = 0.95–0.99 Å) and refined as riding with U iso(H) = 1.2–1.5U eq(C). The N-bound H atom was located in a difference map and refined using isotropic approximation. The F atoms of the –CF3 group are disordered over two positions. Some restraints had to be used to correct the geometry of the disordered components (SADI) and the thermal parameters of the constituent atoms (SIMU). At the conclusion of the refinement, the major component of the disorder had a site occupancy = 0.642(5). The maximum and minimum electron density peaks of 1.04 and 0.65 e Å−3, respectively, were located 0.86 and 0.36 Å from the F1a atom.

Discussion

The piperazine scaffold has been identified as a privileged structure in drug discovery and various piperazine-based derivatives are currently employed as efficient chemotherapeutic agents [5, 6]. Several piperazine-1-carbothioamide derivatives were reported to possess potent anti-bacterial [7, 8] and anti-inflammatory [9] activities. It was in this context that the crystal and molecular structures of the title hybrid piperazine-1-carbothioamide derivative, (I), were studied.

The molecular structure of (I) is shown in the upper image of the figure (50% probability ellipsoids; only the major component of the disordered –CF3 group is shown). The C3–N2–C7–C6 torsion angle is −135.4(2)°, indicating a significant twist about the C7–N2 bond, in order to reduce steric congestion. Despite this rotation, a close intramolecular H1⃛H7b contact of 1.88 Å as well as a C7⃛H1 contact of 2.51 Å are evident. The C3–N1 [1.343(3) Å] and C3–N2 [1.348(3) Å] bond lengths are experimentally equivalent; the C3–S1 bond length is 1.698(2) Å. Further twists in the molecule are manifested in the dihedral angle between the CN2S chromosphere and terminal phenyl ring of 34.00(9)°. The 1,4-di-substituted piperazine ring has a conformation of a chair.

There are two closely related piperazine derivatives in the literature, each of which has a terminal, unsubstituted phenyl ring. In the simplest derivative of these, the N-bound substituent is an adamantan-1-yl group [10] while in the second literature molecule the nitrogen atom is connected to a more complicated fused, three-ring system comprising a five-, six- and five-ring sequence [11]. The equivalent C3–S1 bond lengths in the literature precedents of 1.694(4) and 1.692(4) Å, respectively, are the same as in (I). While for the adamantan-1-yl derivative [adam] the C3–N1 and C3–N3 bond lengths [1.351(4) & 1.369(4) Å] are indistinguishable, there is evidence of disparities in these bonds [1.336(5) & 1.371(6) Å] in the second literature molecule.

As illustrated in the lower view of the figure, supramolecular chains are apparent in the crystal. The molecules in the chain are related by glide symmetry along [001] and are connected by amine–N–H⃛S(thione) hydrogen bonds [N1–H1⃛S1 i : H1⃛S1 i  = 2.63(3) Å, N1⃛S1 i  = 3.372(2) Å with angle at H1 = 151(3)° for symmetry operation (i): x, 1/2 − y, 1/2 + z]. While no N–H⃛S hydrogen bonds are noted in the crystal of the literature adamantan-1-yl structure, probably owing to the bulk of the N-bound substituent, linear chains are apparent in the second literature structure. Connections between zigzag chains in (I), to form an undulating supramolecular layer are of the type C–H⃛F with the shortest of these being a piperazine-methylene–C–H⃛F interaction [C5–H5a⃛F3b ii : H5a⃛F3b ii  = 2.52 Å, C5⃛F3b ii  = 3.390(6) Å with angle at H5a = 147° for (ii): 1 − x, 1 − y, 1 − z], i.e. involving an atom comprising a minor component of the disordered residue. The chains stack along the a-axis in an ⃛ABA⃛ sequence without directional between them.

In order to gain a greater appreciation of the supramolecular association, an analysis for the calculated Hirshfeld surfaces was conducted employing CrystalExplorer 17 [12] in accord with standard methods [13]. The Hirshfeld surfaces were calculated for both the major and minor components of the disordered –CF3 group. The differences in percentage contributions to the surfaces from either component of the disorder were no greater than 1.0% so the following discussion is based on calculations performed for the major component. By far the greater contribution to the Hirshfeld surface was from H⃛H contacts, i.e. 46.2%. Significant contributions also came from F⃛H/H⃛F [22.9%], S⃛H/H⃛S [11.2%] and C⃛H/H⃛C [8.9%] contacts. Relatively minor contributions to the surface were of the type N⃛H/H⃛N [3.2%], F⃛C/C⃛F [3.0%] and F⃛F [2.7%]. The only other contribution to the Hirshfeld surface greater than 0.1% was from C⃛C contacts, i.e. 1.7%.

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

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

  2. Research funding: This work was funded by the Deanship of Scientific Research at Princess Nourah bint Abdulrahman University through the Research Group Program (Grant No. RGP-1442-0010-5).

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

References

1. Rigaku Oxford Diffraction. CrysAlisPro; Rigaku Corporation: Oxford, UK, 2019.Search in Google Scholar

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

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

4. 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, 339–341.10.1107/S0021889808042726Search in Google Scholar

5. Shaquiquzzaman, M., Verma, G., Marella, A., Akhter, M., Akhtar, W., Khan, M. F., Tasneem, S., Alam, M. M. Piperazine scaffold: a remarkable tool in generation of diverse pharmacological agents. Eur. J. Med. Chem. 2015, 102, 487–529; https://doi.org/10.1016/j.ejmech.2015.07.026.Search in Google Scholar PubMed

6. Zhang, R. H., Guo, H. Y., Deng, H., Li, J., Quan, Z. S. Piperazine skeleton in the structural modification of natural products: a review. J. Enzym. Inhib. Med. Chem. 2021, 36, 1165–1197; https://doi.org/10.1080/14756366.2021.1931861.Search in Google Scholar PubMed PubMed Central

7. Foley, T. L., Rai, G., Yasgar, A., Daniel, T., Baker, H. L., Attene–Ramos, M., Kosa, N. M., Leister, W., Burkart, M. D., Jadhav, A., Simeonov, A., Maloney, D. J. 4-(3–Chloro-5-(trifluoromethyl)pyridin-2-yl)–N-(4-methoxypyridin-2-yl)piperazine-1-carbothioamide (ML267), a potent inhibitor of bacterial phosphopantetheinyl transferase that attenuates secondary metabolism and thwarts bacterial growth. J. Med. Chem. 2014, 57, 1063–1078; https://doi.org/10.1021/jm401752p.Search in Google Scholar PubMed PubMed Central

8. Bala, V., Mandalapu, D., Gupta, S., Jangir, S., Kushwaha, B., Chhonker, Y. S., Chandasana, H., Krishna, S., Rawat, K., Krishna, A., Singh, M., Sankhwar, S. N., Shukla, P. K., Maikhuri, J. P., Bhatta, R. S., Siddiqi, M. I., Tripathi, R., Gupta, G., Sharma, V. L. N–Alkyl/aryl-4-(3-substituted-3-phenylpropyl)piperazine-1-carbothioamide as dual-action vaginal microbicides with reverse transcriptase inhibition. Eur. J. Med. Chem. 2015, 101, 640–650; https://doi.org/10.1016/j.ejmech.2015.07.021.Search in Google Scholar PubMed

9. Karthik, C. S., Manukumar, H. M., Sandeep, S., Sudarshan, B. L., Nagashree, S., Mallesha, L., Rakesh, K. P., Sanjay, K. R., Mallu, P., Qin, H. L. Development of piperazine-1-carbothioamide chitosan silver nanoparticles (P1C–Tit*CAgNPs) as a promising anti-inflammatory candidate: a molecular docking validation. MedChemComm 2018, 9, 713–724; https://doi.org/10.1039/c7md00628d.Search in Google Scholar PubMed PubMed Central

10. Al–Abdullah, E. S., Ghabbour, H. A., Alkahtani, H. M., Al–Tamimi, A.–M. S., El–Emam, A. A. Crystal structure of N-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioamide, C21H29N3S. Z. Kristallogr. – New Cryst. Struct. 2016, 231, 991–993.10.1515/ncrs-2016-0056Search in Google Scholar

11. Mishra, K. B., Rajkhowa, S., Tiwari, V. K. An expeditious one-pot synthesis of thiourea derivatives of carbohydrates from sugar azides. J. Carbohydr. Chem. 2020, 29, 334–353.10.1080/07328303.2020.1822997Search in Google Scholar

12. Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D., Spackman, M. A. CrystalExplorer: a program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals. J. Appl. Crystallogr. 2021, 54, 1006–1011.10.1107/S1600576721002910Search in Google Scholar PubMed PubMed Central

13. Tan, S. L., Jotani, M. M., Tiekink, E. R. T. Utilizing Hirshfeld surface calculations, non-covalent interaction (NCI) plots and the calculation of interaction energies in the analysis of molecular packing. Acta Crystallogr. 2019, E75, 308–318.10.1107/S2056989019001129Search in Google Scholar PubMed PubMed Central

Received: 2022-09-08
Accepted: 2022-10-10
Published Online: 2022-10-28
Published in Print: 2023-01-27

© 2022 the author(s), 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 undecacalcium decaarsenide, Ca11As10
  4. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4- ylmethylene)amino)-1,2-dihydro-3H -pyrazol-3-one-κ2 N: O)zinc(II)], C17H16I2N4OZn
  5. The crystal structure of 5,10,15,20-tetrakis(4-(tert-butyl)phenyl)porphyrin-21,23-diido-κ4 N 4-naphthalocyanido-κ4 N 4-neodymium(IV) - chloroform (1/6) C114H90N12Cl18Nd
  6. The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O
  7. Crystal structure of bis[benzyl(methyl)carbamodithioato-κ 2 S,S′]-di-n-butyltin(IV), C26H38N2S4Sn
  8. Crystal structure of (E)-3-(2-(4-(diethylamino)-2-hydroxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate – methanol (1/2), C25H32N2O4S⋅2CH3OH
  9. Synthesis and crystal structure of {(N′,N″-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))-bis(methaneylylidene))bis(2-hydroxybenzohydrazonato)-κ6 N 2 O 4}copper(II), C30H24CuN4O6
  10. The crystal structure of ((E)-2,4-dibromo-6-(((5-(nitro)-2-oxidophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Br2MnN5O4
  11. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3-(p-tolylamino)hexadecahydro-1H-cyclopenta-[a]phenanthren-17-yl)ethan-1-one, C28H41NO
  12. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid—pyrazine-2-carboxamide(1/1), C13H10N4O7
  13. Crystal structure of poly[tetrakis(μ3-2-aminonicotinato-κ3N,O,O′)-(μ2-oxalato-κ4 O,O′:O″,O′″)-(μ4-oxalato-κ6 N:N′:O,O′:O″,O′″)dicopper(I)-disamarium(III)], [SmCu(C6N2H5O2)2(C2O4)] n
  14. The crystal structure of 2,3,4-trihydroxybenzoic- acid—pyrazine-2-carboxamide—water (1/1/1), C12H13N3O7
  15. Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
  16. The crystal structure of 3-anilino-1,4-diphenyl-4H-1,2,4-triazol-1-ium iodide, C20H17N4I
  17. The crystal structure of (tris(2-benzimidazolylmethyl)amine)-benzoato-copper(II) perchlorate monohydrate, CuC31H28N7O7Cl
  18. Crystal structure of [2-hydroxy-3-methyl-benzoato-k1 O-triphenyltin(IV)], C26H22O3Sn
  19. Crystal structure of diaqua-bis(4-(hydroxymethyl)-benzoato-k1 O)zinc(II), C16H18O8Zn
  20. The crystal structure of dicarbonyl-(N-nitroso-N-oxido-phenylamine-κ 2 O,O)-rhodium(I), C8H5N2O4Rh
  21. The crystal structure of oxalic acid – 2-ethoxybenzamide (2/1), C20H24N2O8
  22. The crystal structure of ethyl 7-ethyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C10H15N5O2
  23. Crystal structure of poly[(N,N-dimethylacetamide-κO) (μ4-2-nitroisophthalato-κ 4 O:O′:O″:O′″)manganese(II)], C11H10N2O7Mn
  24. Crystal structure of 14-O-acetyldelcosine, C26H41NO8
  25. The crystal structure of poly[(1,10-phenanthroline-κ2 N,N′)-(μ 4-2-chlorobenzene-1,3-dicarboxylato-κ5 O:O′:O″:O‴) cadmium(II)] monohydrate, C20H13CdClN2O5
  26. Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide) ethanol solvate, C27H26P2S2
  27. Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
  28. Synthesis and crystal structure of dimethyl 2,2′-(2,5-bis(4-hydroxyphenyl)-2,5-dihydrofuran-3,4-diyl)dibenzoate, C34H30O7
  29. Synthesis and crystal structure of 2-(2-oxo-2-phenylethyl)-4H-chromen-4-one, C17H12O3
  30. The crystal structure of tetra(imidazole-κ1 N)zinc(II) μ2-oxido-hexaoxido-divanadium(VI) C12H16N8O6V2Zn
  31. Crystal structure of S-2-(1-(5-methylpyridin-2-ylamino)octyl)-3-hydroxynaphthalene-1,4-dione, C24H28N2O3
  32. Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
  33. The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
  34. Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
  35. Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
  36. The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
  37. The crystal structure of 1,4-bis(1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)-3,6-bis ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-1,4-dialuminacyclohexane – benzene (1/2), C50H72Al2B2O4
  38. Crystal structure of bis(μ 3-diphenylphosphinato)-tetrakis(μ 2-diphenylphosphinato)-bis(diphenylphosphinato)-bis(μ 2-hydroxo)dicopper(II)-ditin(IV), C104H100O18P8Cu2Sn2
  39. Crystal structure of 3-((3,4-dichloroisothiazol-5-yl)methoxy)benzo[d] isothiazole 1,1-dioxide, C11H6Cl2N2O3S2
  40. Synthesis and crystal structure of 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
  41. The crystal structure of tris(carbonyl)-bis(carbonyl)-[μ-propane-1,2- dithiolato]-(benzyldiphenylphosphine)diiron (Fe—Fe), C27H23Fe2O5PS2
  42. Crystal structure of 1-(2-(4-chlorophenethyl)-2-hydroxy-3,3-dimethylbutyl)-1H-1,2,4-triazol-4-ium nitrate, C16H23N4O4Cl
  43. The crystal structure of 3,3′-disulfanediyldi(1H-1,2,4-triazol-5-amine) monohydrate, C4H8N8OS2
  44. The crystal structure of trans-[bis(4-methylpyridine-κN)bis(quinoline-2-carboxylato- κ 2 N,O)cadmium(II)], C32H26CdN4O4
  45. The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
https://doi.org/10.1515/ncrs-2022-0450
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of undecacalcium decaarsenide, Ca11As10
  4. Crystal structure of catena-poly[diiodido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4- ylmethylene)amino)-1,2-dihydro-3H -pyrazol-3-one-κ2 N: O)zinc(II)], C17H16I2N4OZn
  5. The crystal structure of 5,10,15,20-tetrakis(4-(tert-butyl)phenyl)porphyrin-21,23-diido-κ4 N 4-naphthalocyanido-κ4 N 4-neodymium(IV) - chloroform (1/6) C114H90N12Cl18Nd
  6. The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O
  7. Crystal structure of bis[benzyl(methyl)carbamodithioato-κ 2 S,S′]-di-n-butyltin(IV), C26H38N2S4Sn
  8. Crystal structure of (E)-3-(2-(4-(diethylamino)-2-hydroxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate – methanol (1/2), C25H32N2O4S⋅2CH3OH
  9. Synthesis and crystal structure of {(N′,N″-(((ethane-1,2-diylbis(oxy))bis(2,1-phenylene))-bis(methaneylylidene))bis(2-hydroxybenzohydrazonato)-κ6 N 2 O 4}copper(II), C30H24CuN4O6
  10. The crystal structure of ((E)-2,4-dibromo-6-(((5-(nitro)-2-oxidophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Br2MnN5O4
  11. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-10,13-dimethyl-3-(p-tolylamino)hexadecahydro-1H-cyclopenta-[a]phenanthren-17-yl)ethan-1-one, C28H41NO
  12. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid—pyrazine-2-carboxamide(1/1), C13H10N4O7
  13. Crystal structure of poly[tetrakis(μ3-2-aminonicotinato-κ3N,O,O′)-(μ2-oxalato-κ4 O,O′:O″,O′″)-(μ4-oxalato-κ6 N:N′:O,O′:O″,O′″)dicopper(I)-disamarium(III)], [SmCu(C6N2H5O2)2(C2O4)] n
  14. The crystal structure of 2,3,4-trihydroxybenzoic- acid—pyrazine-2-carboxamide—water (1/1/1), C12H13N3O7
  15. Crystal structure of N-ethyl-4-[3-(trifluoromethyl)-phenyl]piperazine-1-carbothioamide, C14H18F3N3S
  16. The crystal structure of 3-anilino-1,4-diphenyl-4H-1,2,4-triazol-1-ium iodide, C20H17N4I
  17. The crystal structure of (tris(2-benzimidazolylmethyl)amine)-benzoato-copper(II) perchlorate monohydrate, CuC31H28N7O7Cl
  18. Crystal structure of [2-hydroxy-3-methyl-benzoato-k1 O-triphenyltin(IV)], C26H22O3Sn
  19. Crystal structure of diaqua-bis(4-(hydroxymethyl)-benzoato-k1 O)zinc(II), C16H18O8Zn
  20. The crystal structure of dicarbonyl-(N-nitroso-N-oxido-phenylamine-κ 2 O,O)-rhodium(I), C8H5N2O4Rh
  21. The crystal structure of oxalic acid – 2-ethoxybenzamide (2/1), C20H24N2O8
  22. The crystal structure of ethyl 7-ethyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C10H15N5O2
  23. Crystal structure of poly[(N,N-dimethylacetamide-κO) (μ4-2-nitroisophthalato-κ 4 O:O′:O″:O′″)manganese(II)], C11H10N2O7Mn
  24. Crystal structure of 14-O-acetyldelcosine, C26H41NO8
  25. The crystal structure of poly[(1,10-phenanthroline-κ2 N,N′)-(μ 4-2-chlorobenzene-1,3-dicarboxylato-κ5 O:O′:O″:O‴) cadmium(II)] monohydrate, C20H13CdClN2O5
  26. Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide) ethanol solvate, C27H26P2S2
  27. Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
  28. Synthesis and crystal structure of dimethyl 2,2′-(2,5-bis(4-hydroxyphenyl)-2,5-dihydrofuran-3,4-diyl)dibenzoate, C34H30O7
  29. Synthesis and crystal structure of 2-(2-oxo-2-phenylethyl)-4H-chromen-4-one, C17H12O3
  30. The crystal structure of tetra(imidazole-κ1 N)zinc(II) μ2-oxido-hexaoxido-divanadium(VI) C12H16N8O6V2Zn
  31. Crystal structure of S-2-(1-(5-methylpyridin-2-ylamino)octyl)-3-hydroxynaphthalene-1,4-dione, C24H28N2O3
  32. Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
  33. The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
  34. Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
  35. Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
  36. The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
  37. The crystal structure of 1,4-bis(1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)-3,6-bis ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-1,4-dialuminacyclohexane – benzene (1/2), C50H72Al2B2O4
  38. Crystal structure of bis(μ 3-diphenylphosphinato)-tetrakis(μ 2-diphenylphosphinato)-bis(diphenylphosphinato)-bis(μ 2-hydroxo)dicopper(II)-ditin(IV), C104H100O18P8Cu2Sn2
  39. Crystal structure of 3-((3,4-dichloroisothiazol-5-yl)methoxy)benzo[d] isothiazole 1,1-dioxide, C11H6Cl2N2O3S2
  40. Synthesis and crystal structure of 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
  41. The crystal structure of tris(carbonyl)-bis(carbonyl)-[μ-propane-1,2- dithiolato]-(benzyldiphenylphosphine)diiron (Fe—Fe), C27H23Fe2O5PS2
  42. Crystal structure of 1-(2-(4-chlorophenethyl)-2-hydroxy-3,3-dimethylbutyl)-1H-1,2,4-triazol-4-ium nitrate, C16H23N4O4Cl
  43. The crystal structure of 3,3′-disulfanediyldi(1H-1,2,4-triazol-5-amine) monohydrate, C4H8N8OS2
  44. The crystal structure of trans-[bis(4-methylpyridine-κN)bis(quinoline-2-carboxylato- κ 2 N,O)cadmium(II)], C32H26CdN4O4
  45. The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
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 30.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2022-0450/html?lang=en&srsltid=AfmBOop5VPYm8hdYoFRzWBkLP8b2CpDAMemOsBzql5AXc1eZUrnuv2Zw
Scroll to top button