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

  • Wen-Xuan Li , Qing-Guo Meng , Gui-Ge Hou ORCID logo , Yong-Jun Liu and Meng Zhang EMAIL logo
Published/Copyright: August 11, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 5

Abstract

C20H18ClF4N3O, monoclinic, P21/c (no. 14), a = 9.6123(7) Å, b = 11.8692(7) Å, c = 16.9510(12) Å, β = 104.798(7)∘, V = 1869.8(2) Å3, Z = 4, Rgt(F) = 0.0444, wRref(F2) = 0.1043, T = 293 K.

CCDC no.: 2272257

The crystal structure is shown in the figure 1. Displacement ellipsoids are drawn at the 40 % 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: Colourless block
Size: 0.12 × 0.10 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.26 mm−1
Diffractometer, scan mode: SuperNova,
θmax, completeness: 25.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 8360, 3489, 0.039
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2830
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 0.6647 (2) 0.59481 (18) 0.05328 (12) 0.0137 (5)
C2 0.6391 (2) 0.69956 (18) 0.02450 (12) 0.0138 (5)
C3 0.6648 (2) 0.73180 (19) −0.05680 (13) 0.0182 (5)
H3A 0.685627 0.811749 −0.057009 0.022*
H3B 0.578550 0.717169 −0.099836 0.022*
C4 0.7900 (2) 0.66525 (19) −0.07322 (14) 0.0202 (5)
H4A 0.790303 0.674163 −0.130057 0.024*
H4B 0.879661 0.695684 −0.040107 0.024*
C5 0.8370 (2) 0.4603 (2) −0.09707 (13) 0.0202 (5)
H5 0.875510 0.482712 −0.139638 0.024*
C6 0.8366 (2) 0.34673 (19) −0.07826 (13) 0.0184 (5)
H6 0.873070 0.293799 −0.108171 0.022*
C7 0.7811 (2) 0.31328 (18) −0.01406 (13) 0.0158 (5)
C8 0.7247 (2) 0.39275 (18) 0.02974 (13) 0.0148 (5)
H8 0.687412 0.369583 0.072590 0.018*
C9 0.7239 (2) 0.50671 (17) 0.00986 (12) 0.0137 (5)
C10 0.7818 (2) 0.54202 (18) −0.05467 (13) 0.0161 (5)
C11 0.5803 (2) 0.78887 (18) 0.07019 (13) 0.0151 (5)
H11 0.499470 0.825895 0.031899 0.018*
C12 0.5603 (2) 0.63519 (18) 0.16456 (13) 0.0145 (5)
C13 0.6931 (2) 0.87868 (18) 0.10639 (12) 0.0138 (5)
C14 0.6536 (2) 0.98680 (18) 0.12123 (13) 0.0151 (5)
C15 0.7499 (2) 1.07043 (18) 0.15486 (12) 0.0160 (5)
H15 0.718947 1.142611 0.163358 0.019*
C16 0.8947 (2) 1.04267 (18) 0.17551 (12) 0.0150 (5)
C17 0.9403 (2) 0.93474 (19) 0.16420 (13) 0.0179 (5)
H17 1.037603 0.916662 0.179880 0.022*
C18 0.8387 (2) 0.85331 (18) 0.12904 (13) 0.0170 (5)
H18 0.869147 0.780933 0.120644 0.020*
C19 0.8341 (3) 0.11889 (19) −0.03067 (14) 0.0206 (5)
H19A 0.787801 0.119732 −0.087997 0.031*
H19B 0.821734 0.046227 −0.008531 0.031*
H19C 0.934908 0.134011 −0.022551 0.031*
C20 1.0058 (3) 1.12925 (19) 0.21086 (14) 0.0213 (5)
Cl1 0.64277 (6) 0.34411 (4) 0.24215 (3) 0.01817 (16)
F1 0.51039 (13) 1.01316 (10) 0.10092 (8) 0.0220 (3)
F2 1.05961 (16) 1.11397 (13) 0.29168 (8) 0.0367 (4)
F3 0.95714 (15) 1.23421 (11) 0.20083 (9) 0.0372 (4)
F4 1.11989 (15) 1.12391 (12) 0.17917 (10) 0.0391 (4)
N1 0.63012 (18) 0.56452 (15) 0.12681 (10) 0.0153 (4)
H1A 0.647102 0.503188 0.148457 0.024 (7)*
N2 0.52671 (18) 0.73798 (15) 0.13564 (11) 0.0157 (4)
H2A 0.477013 0.777579 0.160731 0.022 (7)*
N3 0.52353 (19) 0.60210 (16) 0.23133 (11) 0.0194 (4)
H3C 0.481628 0.646477 0.252868 0.021 (7)*
H3D 0.541558 0.537061 0.249716 0.035 (8)*
O1 0.77133 (16) 0.20348 (12) 0.00972 (9) 0.0196 (4)

1 Source of material

Based on the literature synthesis [4, 5], 7-methoxy-3,4-dihydronaphthalen-1(2H)-one (0.70 g, 4.00 mmol) and 2-fluoro-4-(trifluoromethyl)benzaldehyde (0.77 g, 4.00 mmol) were dissolved in 25 mL methanol. About 5.0 mL of 20 % sodium hydroxide solution was added to the reaction dropwise. The mixture was stirred at room temperature for 3 h to produce a yellow precipitate. The intermediate, (E)-2-(2-fluoro-4-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, is filtered and used directly for the next experiment. Next, the intermediate (1.05 g, 3.00 mmol), guanidine hydrochloride (1.42 g, 15.00 mmol), and potassium hydroxide powder (0.84 g, 15.00 mmol) were added to the mixed solution of anhydrous ethanol (10 mL) and 1, 2-dichloroethane (10 mL). The mixture was heated by reflux for 1.5 h and monitored by thin-layer chromatography (TLC). After filtration, the filtrate used to be removed with the aid of attention below-decreased pressure, and the filtrate used to be purified with silica gel column chromatography (dichloromethane:methanol = 20:1, v/v) after dissolution with dichloromethane. The product used to be dissolved with 5 mL of dichloromethane and 5 mL of methanol and slowly evaporated at room temperature to achieve colourless 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) = 0.93 Å (aromatic), Uiso(H) = 1.2Ueq(C). H atoms on N atom were located in difference maps and treated as riding.

3 Comment

It has been proven that 3,4-dihydronaphthalen-1(2H)-one derivatives have been investigated as novel modulators of allergic and inflammatory phenomena [6]. Wang’s team introduced α, β-unsaturated ketone to get 2-(benzylidene)-3,4-dihydronaphthalen-1(2H)-one derivatives, so that it has two pharmacophores, reducing the toxicity to normal cells [7]. Based on these structural features, some substituted benzo[h]quinazoline derivatives were reported via a Michael addition reaction between 2-(benzylidene)-3,4-dihydronaphthalen-1(2H)-one derivatives and guanidine hydrochloride under base catalysis [8], [9], [10], [11]. Most of these reported compounds are substituted by halogens, methoxys, trifluoromethyl and other substituents. At the same time, they also showed better anti-inflammatory activities. In this paper, 7-methoxy-3,4-dihydronaphthalen-1(2H)-one was used as raw material. The intermediate, (E)-2-(2-fluoro-4-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one was obtained through Claisen–Schmidt condensation between raw material and 2-fluoro-4-(trifluoromethyl)benzaldehyde. Then the target product 4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazoline-2-amine was generated through Michael addition reaction.

Single-crystal structure analysis reveals that there is one cation and one chloride anion in the asymmetric unit (cf. the figure 1). Bond lengths and angles are all in the expected ranges. Structurally, the compound central parent nucleus is 1,4,5,6-tetrahydrobenzo[h]quinazoline-2-amine. Therein, pyrimidine ring is non-aromatic ring with different bond lengths, i.e. Bond length of C(1)–C(2), C(1)–N(1), C(12)–N(1), C(12)–N(2), C(11)–N(2), C(2)–C(11) are 1.335(3), 1.416(3), 1.335(3), 1.324(3), 1.467(3) and 1.505(3) Å, respectively. The pyrimidine ring has one hydrogen atom on each of the two nitrogen atoms. The title compound was isolated as their hydrochloride salts, which keeps them stable [12, 13]. Interestingly, the chloride ion, as a hydrogen-bond acceptor, plays an important role in forming two groups of hydrogen bonds, viz. N(2)–H(2A)⋯Cl(1) and N(3)–H(3C)⋯Cl(1) bonds. It is worth mentioning that there is a chiral C(11) atom at the bridgehead position of 1,4,5,6-tetrahydrobenzo[h]quinazoline-2-amine. In the solid state, a pair of isomers was generated. In one isomer, the C(11) atom adopts a S configuration, while the C(11) atom in another isomer adopts a R configuration [8]. In addition, the benzene ring is substituted with electron-withdrawing substituents (–F and –CF3). Precisely because of the structural characteristics of this chiral center, the substituted benzene ring forms a large dihedral angle between the central parent nucleus and the substituted benzene ring, with the dihedral angle of about 71.7∘.

Corresponding author: Meng Zhang, School of Pharmacy, Binzhou Medical University, Yantai, 264003, P.R. China, 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 supported by Shandong Provincial Natural Science Foundation (No. ZR2023MH190).

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

References

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

2. Sheldrick, G. M. A short history of SHELX. Acta Cryst. 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 Cryst. 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. Barlow, J. W., Zhang, T., Woods, O., Byrne, A. J., Walsh, J. J. Novel mast cell-stabilising amine derivatives of 3,4-dihydronaphthalen-1(2H)-one and 6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one. Med. Chem. 2011, 7, 213–223; https://doi.org/10.2174/157340611795564222.Search in Google Scholar PubMed

7. Wang, F. L., Zhang, R. X., Cui, Y., Sheng, L. P., Sun, Y. P., Tian, W., Liu, X., Liang, S. Design, synthesis and biological evaluation of 3,4-dihydronaphthalen-1(2H)-one derivatives as Bcl-2 inhibitors. Res. Chem. Intermed. 2017, 43, 5933–5942; https://doi.org/10.1007/s11164-017-2972-x.Search in Google Scholar

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

9. 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

10. Luan, M. Z., Zhang, X. F., Yang, Y., Meng, Q. G., Hou, G. G. Anti-inflammatory activity of fluorine-substituted benzo[h]quinazoline-2-amine derivatives as NF-κB inhibitors. Bioorg. Chem. 2023, 132, 106360; https://doi.org/10.1016/j.bioorg.2023.106360.Search in Google Scholar PubMed

11. 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

12. 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-κB 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

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-κB pathway activation. Eur. J. Med. Chem. 2021, 225, 113796; https://doi.org/10.1016/j.ejmech.2021.113796.Search in Google Scholar PubMed

Received: 2023-07-19
Accepted: 2023-08-01
Published Online: 2023-08-11
Published in Print: 2023-10-26

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

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  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
https://doi.org/10.1515/ncrs-2023-0334
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of (N-([1,1′:4′,1″-terphenyl]-4,4′-diethyl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide-κ4N,N,N″, O)tri(nitrato-kO, O′) samarium(III) - methanol - acetonitrile (1/1/1), C40H39SmN8O14
  4. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(2-chloro-4-methyl phenolate-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV), C27H27Cl2N3O6Ti
  5. N′-[(1E)-(4–Fluorophenyl)methylidene]adamantane-1-carbohydrazide, C18H21FN2O
  6. Crystal structure of 4-bromo-3-nitro-1H-pyrazole-5-carboxylic acid monohydrate, C4H2N3BrO4·H2O
  7. Crystal structure of dipyridine-k1N-tris(2,2,6,6-tetramethyl-5-oxohept-3-en-3-olato-k2O,O′)dysprosium(III), DyC43H67O6N2
  8. Crystal structure of cyclo[tetraiodido-bis{μ2-1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-isopropyl-imidazol)-k2N:N}dicadmiun(II)], C26H30N10Cd2I4
  9. The crystal structure of tert-butyl (E)-3-(2-(benzylideneamino)phenyl)-1H-indole-1-carboxylate, C26H24N2O2
  10. The crystal structure of 4-(3-carboxy-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4- dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 2,5-dihydroxybenzoate methanol solvate, C27H32FN3O9
  11. Crystal structure of (μ2-1-(4,4′-bipyridine-κ2N:N′)-bis[diaqua-(4-iodopyridine-2,6-dicarboxylato-κ3O,N,O′)–cobalt(II)], C24H20Co2I2N4O12
  12. The crystal structure of dimethyl 4,4′-(10,20-diphenylporphyrin-5,15-diyl)dibenzoate dichloromethane solvate, C49H36N4O4Cl2
  13. (E)-2-((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ylidene)hydrazine-1-carbothioamide C14H23N3S1
  14. The crystal structure of [1-(4-(trifluoromethyl)phenyl)-3,4-dihydroquinolin-2(1H)-one], C16H12F3NO
  15. Crystal structure of (E)-2-amino-N′-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)benzohydrazide – dimethylformamide – water (1/1/2), C15H16N4O3·C3H7NO·2H2O
  16. Crystal structure of 3-(4-bromophenyl)-5-methyl-1H-pyrazole, C10H9BrN2
  17. Crystal structure of 1,10-phenanthrolinium bromide dihydrate, C12H9N2Br
  18. Crystal structure of N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, C13H10ClNO
  19. The crystal structure of nitroterephthalic acid, C8H5NO6
  20. Crystal structure of (2-((4-bromo-2,6-dichlorophenyl)amino)phenyl) (morpholino)methanone, C17H15BrCl2N2O2
  21. Crystal structure of tetraaqua-bis(ethanol-κO)-tetrakis(μ2-trifluoroacetate-κ2O:O′)-bis(trifluoroacetate-κ2O)digadolinium(III) Gd2C16H20O18F18
  22. The crystal structure of dimethyl 4,4′-[10,20-bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate chloroform solvate, C50H32Cl6F4N4O4
  23. The crystal structure of N,N′-((nitroazanediyl)bis(methylene))diacetamide, C6H12O4N4
  24. The crystal structure of [bis(2,2′-bipyridine-6-carboxylato-κ3N,N,O)magnesium(II)]dihydrate, C22H18N4O6Mg
  25. Crystal structure of poly[diaqua-(bis(μ2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′] cobalt(II)-tetraqua-bis(1,4-bis(imidazol-1-ylmethyl)benzene)-κ1N)-cobalt(II) di(2,5-thiophenedicarboxylate) dihydrate, C68H76Co2N16O16S2
  26. Crystal structure of poly[chlorido-μ2-chlorido-(μ2-1-[(2-ethyl-4-methyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κN:N’)cadmium(II)], C13H15CdN5Cl2
  27. The crystal structure of (4-hydroxybenzenesulfonate)-k1O-6,6′-((1E,1′E)- (ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene)) bis(2-methoxyphenol)-κ2N,N,μ2O,O,κ2O, O)-(methanol)-cobalt(II) sodium(I), C25H27CoN2NaO9S
  28. Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)(4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O
  29. Crystal structure of bis{[(cyclohexylimino)(phenylimino)-l5-(methyl)diethylazane-κ2N:N′]-(ethyl)-zinc(II)]}, C38H62N6Zn2
  30. Crystal structure of 2-[(4-bromobenzyl)thio]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C13H8Br2N2OS2
  31. Crystal structure of 10-methoxy-7,11b,12,13-tetrahydro-6H-pyrazino [2′,3′:5,6]pyrazino[2,1-a]isoquinoline, C15H16N4O
  32. The crystal structure of 1-propyl-2-nitro-imidazole oxide, C6H9N3O3
  33. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid–2-ethoxybenzamide (1/1), C17H16N2O8
  34. The structure of RUB-1, (C8H16N)6[B6Si48O108], a boron containing levyne-type zeolite, occluding N-methyl-quinuclidinium in the cage-like pores
  35. The crystal structure of diaqua-(naphthalene-4,5-dicarboxylate-1,8-dicarboxylic anhydride-κ1O)-(4′-(4-(1H-benzimidazolyl-1-yl)phenyl)-2,2′:6′,2″-terpyridine-κ3N,N′,N″)–manganese(II) dihydrate, C42H27MnN5O9·2H2O
  36. Crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene))bis (3-(3-bromopropoxy)phenol), C20H22Br2N2O4
  37. The crystal structure of 3-(2-hydroxyphenyl)-4-phenyl-6-(p-tolyl)-2H-pyran-2-one, C24H18O3
  38. Crystal structure of bis(μ2-2-(1,5-dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)-(nitrato-κ2O,O′)dicobalt(II), C36H32Co2N8O4
  39. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2
  40. The crystal structure of 4-aminiumbiphenyl benzenesulfonate, C18H17NO3S
  41. Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9
  42. Crystal structure of N-(Ar)-N′-(Ar′)-formamidine, C14H12Br2N2O
  43. The crystal structure of 4-(2,4-dichlorophenyl)-2-(4-fluorophenyl)-5-methyl-1H-imidazole, C16H11Cl2FN2
  44. Crystal structure of 1-(4–chlorophenyl)-4-benzoyl-3-methyl-1H-pyrazol-5-ol, C17H13ClN2O2
  45. The crystal structure of 5-amino-1-methyl-4-nitroimidazole, C4H6O2N4
  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
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