Home Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
Article Open Access

Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O

  • Lu Yu , Qing-Guo Meng , Gui-Ge Hou ORCID logo , Yong-Jun Liu and Zi-Kai Geng EMAIL logo
Published/Copyright: October 11, 2023
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 6

Abstract

C20H18ClF4N3O, orthorhombic, Pbca (no. 61), a = 12.5254(4) Å, b = 12.6845(5) Å, c = 24.1490(11) Å, V = 3836.8(3) Å3, Z = 8, R gt (F) = 0.0485, wR ref (F2) = 0.1343, T = 293 K.

CCDC no.: 2272279

The crystal structure is shown in the Figure. Displacement ellipsoids are drawn at the 30 % probability level.

Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Yellow block
Size: 0.15 × 0.14 × 0.12 mm
Wavelength: Cu Kα radiation (1.54178 Å)
μ: 2.27 mm−1
Diffractometer, scan mode: XtaLAB AFC12 (RINC)
θmax, completeness: 73.9°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 15,274, 3805, 0.054
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 3361
N(param)refined: 267
Programs: CrysAlisPRO [1], SHELX [2, 3]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.30840 (16) 0.12858 (17) 0.96703 (8) 0.0246 (4)
C2 0.23258 (17) −0.03005 (17) 0.92281 (9) 0.0254 (4)
H2 0.196956 −0.087685 0.942537 0.031*
C3 0.42679 (17) 0.00620 (16) 0.92360 (8) 0.0242 (4)
C4 0.34727 (17) −0.06157 (17) 0.91374 (8) 0.0255 (4)
C5 0.37032 (17) −0.17070 (18) 0.89178 (9) 0.0288 (5)
H5A 0.307908 −0.197654 0.872669 0.035*
H5B 0.386304 −0.217742 0.922342 0.035*
C6 0.46457 (17) −0.16732 (19) 0.85214 (10) 0.0300 (5)
H6A 0.486494 −0.238748 0.843386 0.036*
H6B 0.442855 −0.133391 0.817949 0.036*
C7 0.66270 (18) −0.13206 (18) 0.86310 (10) 0.0303 (5)
H7 0.676359 −0.191188 0.841456 0.036*
C8 0.74780 (17) −0.07028 (18) 0.88084 (9) 0.0295 (5)
H8 0.817419 −0.088135 0.871275 0.035*
C9 0.72789 (17) 0.01795 (18) 0.91283 (9) 0.0272 (5)
C10 0.62408 (17) 0.04198 (17) 0.92874 (9) 0.0267 (4)
H10 0.611432 0.099480 0.951717 0.032*
C11 0.53901 (16) −0.01928 (17) 0.91057 (8) 0.0243 (4)
C12 0.55823 (17) −0.10792 (18) 0.87679 (9) 0.0270 (4)
C13 0.17654 (16) −0.01599 (18) 0.86689 (9) 0.0262 (4)
C14 0.20727 (17) 0.06165 (17) 0.82983 (9) 0.0269 (5)
C15 0.16062 (19) 0.07353 (19) 0.77779 (9) 0.0330 (5)
C16 0.0802 (2) 0.0040 (2) 0.76248 (10) 0.0407 (6)
H16 0.047463 0.010721 0.728103 0.049*
C17 0.0488 (2) −0.0752 (2) 0.79826 (11) 0.0405 (6)
H17 −0.004475 −0.122119 0.787646 0.049*
C18 0.09643 (18) −0.0851 (2) 0.85013 (9) 0.0326 (5)
H18 0.074436 −0.138563 0.873875 0.039*
C19 0.2015 (2) 0.1571 (2) 0.73930 (10) 0.0400 (6)
C20 0.90917 (17) 0.07421 (19) 0.90861 (10) 0.0318 (5)
H20A 0.939270 0.008785 0.921084 0.048*
H20B 0.953645 0.131551 0.920490 0.048*
H20C 0.904789 0.074016 0.868927 0.048*
Cl1 0.53974 (4) 0.31046 (4) 0.97499 (2) 0.02830 (16)
F1 0.28703 (10) 0.12832 (10) 0.84377 (5) 0.0310 (3)
F2 0.30268 (14) 0.13926 (13) 0.72382 (7) 0.0561 (5)
F3 0.20003 (13) 0.25397 (12) 0.76144 (6) 0.0452 (4)
F4 0.14390 (17) 0.16261 (15) 0.69268 (6) 0.0643 (5)
N1 0.40529 (14) 0.10538 (14) 0.94739 (7) 0.0251 (4)
H1A 0.458166 0.152892 0.953256 0.033 (7)*
N2 0.22689 (14) 0.06415 (14) 0.95774 (7) 0.0261 (4)
H2A 0.164557 0.082781 0.970729 0.031 (7)*
N3 0.29398 (14) 0.21691 (15) 0.99561 (8) 0.0279 (4)
H3A 0.347756 0.251484 1.003201 0.045 (8)*
H3B 0.229409 0.229185 1.008687 0.042 (8)*
O1 0.80455 (12) 0.08656 (13) 0.93148 (7) 0.0316 (4)

1 Source of material

Based on literature synthetic techniques [4, 5], using 20 % sodium hydroxide solution (5.0 mL) as a catalyst, 7-methoxy-3,4-dihydronaphthalen-1(2H)-one (0.70 g, 4.00 mmol) was mixed with 2-fluoro-3-(trifluoromethyl)benzaldehyde (0.77 g, 4.00 mmol) in 25 mL of methanol with stirring for 3 h at room temperature to produce a yellow precipitate. Filtration gave an intermediate: (E)-2-(2-fluoro-3-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one. The intermediate (0.830 g, 2.37 mmol), guanidine hydrochloride (1.58 g, 16.59 mmol) and potassium hydroxide (0.931 g, 16.59 mmol) were added to a mixture of anhydrous ethanol (10 mL) and dichloroethane (10 mL), and the reaction was carried out at 90 °C for 2 h. The reaction was monitored by Thin–Layer Chromatography (TLC, PE:EA = 8:1, v/v). The filtered filtrate is depressurized to remove the solvent. Dichloromethane/methanol (20:1, v/v) was used as eluent to separate and purify by the silica gel column. The obtained product was dissolved in a solution of dichloromethane (5 mL) and methanol (5 mL), and slowly evaporated at room temperature to achieve appropriate yellow crystals.

2 Experimental details

The H atoms were placed in idealized positions and treated as riding on their parent atoms, with d(C–H) = 0.96 Å(methyl), Uiso(H) = 1.5Ueq(C), and d(C–H) = 0.97 Å(methylene), Uiso(H) = 1.2Ueq(C), and d(C–H) = 0.98 Å(methyne), Uiso(H) = 1.2Ueq(C), and d(C–H) = 0.93 Å(aromatic), Uiso(H) = 1.2Ueq(C). H atoms on N atom were located in different maps and treated as riding.

3 Comment

3,4–Dihydronaphthalene-1(2H)-one derivatives have been used in previous studies as formulations and inhibitors of novel anti-allergic, anti-inflammatory drugs and retinoic acid metabolic enzymes [6]. It contains two pharmacophores: 3,4-dihydronaphthalen-1(2H)-one and an α,β-unsaturated token. These two pharmacophores can be used as the main binding sites [4]. The 1,4,5,6-tetrahydrobenzo[h]quinazoline-2-amine skeleton structure formed by the condensation of α,β-unsaturated ketones with guanidinium chloride that can effectively improve the water solubility [7]. The substitution of the trifluoromethyl group can transform the substituent into a powerful electron-withdrawing group, which can slightly increase lipophilicity [8]. In this study, the Claisen–Schmidt reaction of 7-methoxy-3,4-dihydronaphthalene-1(2H)-one with 2-fluoro-3-(trifluoromethyl)benzaldehyde to form the intermediate (E)-2-(2-fluoro-3-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalene-1(2H)-one was investigated. The target product: 4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-2-amine was obtained by the condensation of the intermediate with guanidinium chloride hydrochloride.

Single crystals were obtained by evaporation from dichloromethane/methanol solution at room temperature. The single crystal structure analysis shows that 2-fluoro-4-(trifluoromethyl)phenyl and carbonyl groups adopt E stereochemistry. There is a chiral C(2) atom at the bridgehead position of 1,4,5,6-tetrahydrobenzo[h]quinazoline-2-amine. In the solid state, the molecules crystallize in an orthorhombic group Pbca, and the whole does not show chiral properties. However, the crystal generates two isomers, which one is the S configuration and the other is the R configuration [9]. The benzene ring at C(2) atom is substituted by electron-withdrawing substituents (–F and –CF3). Because of the chiral structural characteristics and the substituent effect, there is a large dihedral angle between the central parent nucleus and the substituted benzene ring, with the dihedral angle of about 84.98(3)°. This twisting structure may increase the possibility of interaction with bioactive molecules [10]. In addition, the pyrimidine ring is non-aromatic ring, which is different from aromatic pyrimidine ring in 5,6-dihydrobenzo[h]quinazolin-2-amine derivatives [11, 12]. In this study, the non-aromatic pyrimidine ring has different bond lengths, i.e. bond lengths of C(1)–N(1), C(1)–N(2), C(2)–N(2), C(2)–C(4), C(3)–C(4), C(3)–N(1) are 1.336(3), 1.327(3), 1.464(3), 1.507(3), 1.337(3) and 1.409(3) Å, respectively. Interestingly, 1,4,5,6-tetrahydrobenzo[h]quinazoline-2-amine has a positive charge and forms a stable structure with a chloride ion [13, 14]. The chloride ion, as a hydrogen-bond acceptor, was stabilized by three groups of hydrogen bonds, viz. N(1)–H(1A)⋯Cl(1), N(3)–H(3A)⋯Cl(1) and C(10)–H(10)⋯Cl(1) bonds.

Corresponding author: Zi-Kai Geng, School of Pharmacy, Binzhou Medical University, Yantai, 264003, P.R. China, E-mail:

Funding source: Shandong Provincial Natural Science Foundation

Award Identifier / Grant number: ZR2023MH190

Funding source: Project of Improving Innovation Ability of Small and Medium-Sized Sci-Tech Enterprises in Shandong Province

Award Identifier / Grant number: 2023TSGC0870

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

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

  3. Research funding: This work was supported by Shandong Provincial Natural Science Foundation (No. ZR2023MH190) and Project of Improving Innovation Ability of Small and Medium-Sized Sci-Tech Enterprises in Shandong Province (No. 2023TSGC0870).

References

1. Rigaku OD. CrysAlisPRO; Rigaku Oxford Diffraction Ltd: Yarnton, Oxfordshire, England, 2017.Search in Google Scholar

2. 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

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

4. Sun, Y., Zhou, Y. Q., Liu, Y. K., Zhang, H. Q., Hou, G. G., Meng, Q. G., Hou, Y. Potential anti-neuroinflammatory NF-κB inhibitors based on 3,4-dihydronaphthalen-1(2H)-one derivatives. J. Enzyme Inhib. Med. Chem. 2020, 35, 1631–1640; https://doi.org/10.1080/14756366.2020.1804899.Search in Google Scholar PubMed PubMed Central

5. Luan, M. Z., Wang, H. Y., Zhang, M., Song, J., Hou, G. G., Zhao, F. L., Meng, Q. G. Crystal structure of (E)-2-(3,5-bis(trifluoromethyl) benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C20H14F6O2. Z. Kristallogr. N. Cryst. Struct. 2021, 236, 61–63; https://doi.org/10.1515/ncrs-2020-0446.Search in Google Scholar

6. Kirby, A. J., Le, L. R., Maharlouie, F., Mason, P., Nicholls, P. J., Smith, H. J. Inhibition of retinoic acid metabolising enzymes by 2-(4-aminophenylmethyl)-6-hydroxy-3,4-dihydronaphthalen-1(2H)-one and related compounds. J. Enzyme Inhib. Med. Chem. 2003, 18, 27–33; https://doi.org/10.1080/1475636021000049221.Search in Google Scholar PubMed

7. Sun, Y., Gao, Z. F., Wang, C. H., Hou, G. G. Synthesis, crystal structures and anti-inflammatory activity of fluorine-substituted 1,4,5,6-tetrahydrobenzo[h]quinazolin-2-amine derivatives. Acta Crystallogr. 2019, C75, 1157–1165; https://doi.org/10.1107/s2053229619010118.Search in Google Scholar

8. Swallow, S. Fluorine in medicinal chemistry. Prog. Med. Chem. 2015, 54, 65–133; https://doi.org/10.1016/bs.pmch.2014.11.001.Search in Google Scholar PubMed

9. Li, W. X., Meng, Q.-G., Hou, G.-G., Liu, Y. J., Zhang, M. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O. Z. Kristallogr. N. Cryst. Struct. 2023, 238, 1021–1023; https://doi.org/10.1515/ncrs-2023-0334.Search in Google Scholar

10. Sun, Y., Gao, Z. F., Yan, W. B., Yao, B. R., Xin, W. Y., Wang, C. H., Meng, Q. G., Hou, G. G. Discovery of novel NF-kappa B inhibitor based on scaffold hopping: 1,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine. Eur. J. Med. Chem. 2020, 198, 112366; https://doi.org/10.1016/j.ejmech.2020.112366.Search in Google Scholar PubMed

11. Zhang, X. F., Luan, M. Z., Yan, W. B., Zhao, F. L., Hou, Y., Hou, G. G., Meng, Q. G. Anti-neuroinflammatory effects of novel 5,6-dihydrobenzo[h]quinazolin-2-amine derivatives in lipopolysaccharide-stimulated BV2 microglial cells. Eur. J. Med. Chem. 2022, 235, 114322; https://doi.org/10.1016/j.ejmech.2022.114322.Search in Google Scholar PubMed

12. Li, R. K., Wang, C. H., Hou, G. G., Li, C. B. Crystal structure of 9-(2-chloroethoxy)-4-(4-methoxy-3-(trifluoromethyl)phenyl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C22H19ClF3N3O2. Z. Kristallogr. N. Cryst. Struct. 2023, 238, 243–245; https://doi.org/10.1515/ncrs-2022-0589.Search in Google Scholar

13. Zhou, Y.-Q., Sun, Y., Luo, H.-L., Gao, Z.-F., Zhang, H.-Q., Meng, Q.-G., Bai, X.-Y., Hou, G.-G., Hou, Y. Discovery of anti-hepatoma agents from 1,4,5,6,7,8-hexahydropyrido[4,3-d]pyrimidine by inhibiting PI3K/AKT/NF-kappa B pathway activation. Eur. J. Med. Chem. 2021, 225, 113796; https://doi.org/10.1016/j.ejmech.2021.113796.Search in Google Scholar PubMed

14. Yang, Y., Gao, Z. F., Hou, G. G., Meng, Q. G., Hou, Y. Discovery of anti-neuroinflammatory agents from 1,4,5,6-tetrahydrobenzo[2,3]oxepino[4,5-d]pyrimidin-2-amine derivatives by regulating microglia polarization. Eur. J. Med. Chem. 2023, 259, 115688; https://doi.org/10.1016/j.ejmech.2023.115688.Search in Google Scholar PubMed

Received: 2023-08-16
Accepted: 2023-09-29
Published Online: 2023-10-11
Published in Print: 2023-12-15

© 2023 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 bis(dimethylammonium) poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6O1, N2:O2:O3:O1′,N2′]nickel (II)], C22H26N6NiO8
  4. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-((pyridin-4-ylmethyl)amino)benzoato-κ2N:O)cobalt(II)] – 4,4′-bipyridine – water (1/2/2)
  5. Crystal structure of (2S,3S,4S,5S, Z)-2,3,5,6-tetrakis(benzyloxy)-4-hydroxyhexanal oxime, C34H37NO6
  6. The crystal structure of hexakis(3-thiophenecarboxylato-κ2O,O″)-bis(1,10-phenanthroline-κ2N,N′) trimanganese(II), C54H34N4O12S6Mn3
  7. Crystal structure of catena-poly[(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(4-bromobenzoate-κ2O:O′)-(μ-2-bromobenzoate-κ2O,O′)nickel(II)] – water (2/1), C30H21Br2N2NiO4.5
  8. The crystal structure of poly[(μ3-1,3-phenylenedioxydiacetate-κ5O,O,O′,O″,O‴)-bis(4′-(4-(1H-imidazol-1-yl)phenyl)-4,2′:6′,4″-terpyridine-kN) cadmium(II)], C58H42CdN10O6
  9. The crystal structure of 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium 4-methylbenzenesulfonate
  10. Crystal structure of poly[(μ-benzoato)-(μ-cis-4–hydroxy-D-proline)lithium], C12H14LiNO5
  11. The crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O′)-copper(II)] monohydrate, C7H6NO6ICu
  12. The crystal structure of catena-[diaqua-(4-acetylphenoxyacetato-κ2O,O)-bis(4-acetylphenoxyacetato-κ3O,O:O)-dihydrate-lanthanum(III)]–4,4′-bipyridine (2/1), C35H35NO14La
  13. The crystal structure of catena-poly[(4-iodopyridine-2,6-dicarboxylato-κ4 O,N,O′,O′′)(4-imidazol-1-yl-pyridine-κN)copper(II)], C15H9N4O4ICu
  14. Crystal structure of polybis(μ 4-3,5-dicarboxylatopyrazol-1-yl)-bis(N,N-dimethylformamide)tri-copper(II)–acetonitrile (1/2), C20H22Cu3N8O10
  15. Crystal structure of poly[(μ2-5-hydroxy-isophthalato-κ4O,O′:O″,O‴)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)cadmium(II)], C21H24CdN4O5
  16. The crystal structure of poly[bis(μ2-1,4-bi(1-imidazolyl)benzene-κ2N:N′)bis(μ2-4,4′-methylenebis(3-hydroxy-2-naphthoate)-κ2O:O′)cobalt(II)], C35H24CoN4O6
  17. The crystal structure of a cobalt-vanadium-oxido hydrate
  18. The crystal structure of catena-poly[(μ 2-2H-1,2,3-triazole-4,5-dicarboxylato-κ 2 O, O′)-(μ 2-1,3-bis((1H-imidazol-1-yl)methyl)benzene-κ 2 N,N′) zinc(II)], C18H15N7O4Zn
  19. Crystal structure of poly[diaqua-(bis(m2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′-manganese] dichloride, C28H32MnN8O2Cl2
  20. The crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino [3,2-a]isoquinolin-7-ium (E)-3-(4-nitrophenyl)acrylate pentahydrate, C29H34N2O13
  21. Crystal structure of poly[(μ6-ammoniotris(methylene))tris(hydrogen phosphonato)cadmium(II)], C3H10CdNO9P3
  22. Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
  23. The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
  24. Crystal structure of (E)-2-(2-(4-(diethylamino)styryl)-1-ethyl-1,4-dihydroquinolin-4-yl) malononitrile, C26H26N4
  25. Crystal structure of ethyl 2-((2,6-dichloro-4-(cyanomethyl)phenyl) amino)benzoate, C17H14Cl2N2O2
  26. Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
  27. The crystal structure of bis(acetonitrile-κ1N)tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)rhodium(II) (Rh–Rh), C32H18F8O8N2Rh2
  28. The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid, C11H8O3
  29. The crystal structure of [(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)-2,2′-bipyridine-κ2N-copper(II)] tetrahydrate, C22H23N3O9Cu
  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylato−κ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″ )-(dihydrogen L-malate-κ2O,O ′)copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3
https://doi.org/10.1515/ncrs-2023-0374
Creative Commons
BY 4.0

Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of bis(dimethylammonium) poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6O1, N2:O2:O3:O1′,N2′]nickel (II)], C22H26N6NiO8
  4. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-((pyridin-4-ylmethyl)amino)benzoato-κ2N:O)cobalt(II)] – 4,4′-bipyridine – water (1/2/2)
  5. Crystal structure of (2S,3S,4S,5S, Z)-2,3,5,6-tetrakis(benzyloxy)-4-hydroxyhexanal oxime, C34H37NO6
  6. The crystal structure of hexakis(3-thiophenecarboxylato-κ2O,O″)-bis(1,10-phenanthroline-κ2N,N′) trimanganese(II), C54H34N4O12S6Mn3
  7. Crystal structure of catena-poly[(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(4-bromobenzoate-κ2O:O′)-(μ-2-bromobenzoate-κ2O,O′)nickel(II)] – water (2/1), C30H21Br2N2NiO4.5
  8. The crystal structure of poly[(μ3-1,3-phenylenedioxydiacetate-κ5O,O,O′,O″,O‴)-bis(4′-(4-(1H-imidazol-1-yl)phenyl)-4,2′:6′,4″-terpyridine-kN) cadmium(II)], C58H42CdN10O6
  9. The crystal structure of 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium 4-methylbenzenesulfonate
  10. Crystal structure of poly[(μ-benzoato)-(μ-cis-4–hydroxy-D-proline)lithium], C12H14LiNO5
  11. The crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O′)-copper(II)] monohydrate, C7H6NO6ICu
  12. The crystal structure of catena-[diaqua-(4-acetylphenoxyacetato-κ2O,O)-bis(4-acetylphenoxyacetato-κ3O,O:O)-dihydrate-lanthanum(III)]–4,4′-bipyridine (2/1), C35H35NO14La
  13. The crystal structure of catena-poly[(4-iodopyridine-2,6-dicarboxylato-κ4 O,N,O′,O′′)(4-imidazol-1-yl-pyridine-κN)copper(II)], C15H9N4O4ICu
  14. Crystal structure of polybis(μ 4-3,5-dicarboxylatopyrazol-1-yl)-bis(N,N-dimethylformamide)tri-copper(II)–acetonitrile (1/2), C20H22Cu3N8O10
  15. Crystal structure of poly[(μ2-5-hydroxy-isophthalato-κ4O,O′:O″,O‴)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)cadmium(II)], C21H24CdN4O5
  16. The crystal structure of poly[bis(μ2-1,4-bi(1-imidazolyl)benzene-κ2N:N′)bis(μ2-4,4′-methylenebis(3-hydroxy-2-naphthoate)-κ2O:O′)cobalt(II)], C35H24CoN4O6
  17. The crystal structure of a cobalt-vanadium-oxido hydrate
  18. The crystal structure of catena-poly[(μ 2-2H-1,2,3-triazole-4,5-dicarboxylato-κ 2 O, O′)-(μ 2-1,3-bis((1H-imidazol-1-yl)methyl)benzene-κ 2 N,N′) zinc(II)], C18H15N7O4Zn
  19. Crystal structure of poly[diaqua-(bis(m2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′-manganese] dichloride, C28H32MnN8O2Cl2
  20. The crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino [3,2-a]isoquinolin-7-ium (E)-3-(4-nitrophenyl)acrylate pentahydrate, C29H34N2O13
  21. Crystal structure of poly[(μ6-ammoniotris(methylene))tris(hydrogen phosphonato)cadmium(II)], C3H10CdNO9P3
  22. Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
  23. The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
  24. Crystal structure of (E)-2-(2-(4-(diethylamino)styryl)-1-ethyl-1,4-dihydroquinolin-4-yl) malononitrile, C26H26N4
  25. Crystal structure of ethyl 2-((2,6-dichloro-4-(cyanomethyl)phenyl) amino)benzoate, C17H14Cl2N2O2
  26. Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
  27. The crystal structure of bis(acetonitrile-κ1N)tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)rhodium(II) (Rh–Rh), C32H18F8O8N2Rh2
  28. The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid, C11H8O3
  29. The crystal structure of [(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)-2,2′-bipyridine-κ2N-copper(II)] tetrahydrate, C22H23N3O9Cu
  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylato−κ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N′,N″ )-(dihydrogen L-malate-κ2O,O ′)copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3
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 7.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2023-0374/html
Scroll to top button