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Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2

  • Xue Zeng ORCID logo , Yuanjiao Feng ORCID logo EMAIL logo , Wenwu Zhong and Yuanfang Hou
Published/Copyright: November 26, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 1

Abstract

C20H24N2O2, monoclinic, P21 (no. 4), a = 8.0021(9) Å, b = 5.9588(7) Å, c = 18.7274(19) Å, β = 93.546(7)°, V = 891.27(17) Å3, Z = 2, R gt (F) = 0.0408, wR ref (F 2) = 0.1208, T = 300 K.

CCDC no.: 2402218

Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.23 × 0.22 × 0.21 mm
Wavelength: Cu Kα radiation (1.54178 Å)
μ: 0.62 mm−1
Diffractometer, scan mode: φ and ω
θ max, completeness: 68.3°, 99 %
N(hkl)measured, N(hkl)unique, R int: 7,510, 2,770, 0.041
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2,292
N(param)refined: 218
Programs: Olex2, 1 SHELX 2 , 3
Table 2:

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

Atom x y z U iso*/U eq
C1 0.2339 (3) 0.4615 (6) 0.09447 (14) 0.0683 (8)
H1 0.281723 0.324781 0.108242 0.082*
C2 0.3086 (4) 0.5949 (9) 0.04465 (17) 0.0890 (11)
H2 0.407239 0.547196 0.025666 0.107*
C3 0.2398 (4) 0.7941 (7) 0.02325 (16) 0.0849 (11)
H3 0.290095 0.881266 −0.010591 0.102*
C4 0.0973 (4) 0.8647 (7) 0.05164 (15) 0.0784 (9)
H4 0.049878 1.001178 0.037272 0.094*
C5 0.0218 (4) 0.7356 (6) 0.10173 (14) 0.0655 (8)
H5 −0.075535 0.786963 0.121017 0.079*
C6 0.0884 (3) 0.5322 (5) 0.12351 (12) 0.0525 (6)
C7 0.0021 (3) 0.3866 (5) 0.17591 (12) 0.0552 (7)
H7A −0.098953 0.461656 0.189169 0.066*
H7B −0.030690 0.246659 0.152607 0.066*
C8 0.1475 (3) 0.5400 (5) 0.28145 (12) 0.0558 (7)
H8A 0.044884 0.610385 0.295029 0.067*
H8B 0.204349 0.644421 0.251474 0.067*
C9 0.2582 (3) 0.4896 (5) 0.34794 (13) 0.0606 (7)
H9A 0.362961 0.425160 0.334403 0.073*
H9B 0.283304 0.627819 0.373783 0.073*
C10 0.1214 (3) 0.1310 (5) 0.35537 (13) 0.0558 (6)
H10A 0.055511 0.038775 0.385768 0.067*
H10B 0.219030 0.045201 0.343691 0.067*
C11 0.0179 (3) 0.1866 (5) 0.28711 (12) 0.0537 (6)
H11A −0.009801 0.048942 0.261396 0.064*
H11B −0.085945 0.257022 0.299132 0.064*
C12 0.2285 (3) 0.3200 (5) 0.46605 (12) 0.0465 (5)
C13 0.3301 (3) 0.4845 (6) 0.49972 (13) 0.0610 (7)
H13 0.368937 0.601828 0.472506 0.073*
C14 0.3746(3) 0.4780(6) 0.57195(13) 0.0610(7)
H14 0.440465 0.592379 0.592437 0.073*
C15 0.3233(3) 0.3051(5) 0.61451(12) 0.0520(6)
C16 0.2251(3) 0.1401(5) 0.58155(13) 0.0630(8)
H16 0.189499 0.020901 0.608852 0.076*
C17 0.1780 (3) 0.1461 (5) 0.50973 (14) 0.0605 (7)
H17 0.111138 0.031811 0.489820 0.073*
C18 0.3705 (3) 0.2914 (5) 0.69206 (13) 0.0588 (7)
C19 0.5317 (3) 0.4551 (7) 0.78971 (13) 0.0687 (8)
H19A 0.643144 0.518911 0.796007 0.082*
H19B 0.535932 0.303394 0.808528 0.082*
C20 0.4138 (4) 0.5908 (8) 0.82984 (17) 0.0885 (11)
H20A 0.406809 0.739571 0.810174 0.133*
H20B 0.453280 0.598593 0.879244 0.133*
H20C 0.305068 0.522326 0.826101 0.133*
N1 0.1070 (2) 0.3364 (4) 0.24113 (10) 0.0503 (5)
N2 0.1751 (2) 0.3332 (3) 0.39408 (10) 0.0504 (5)
O1 0.3198 (3) 0.1503 (5) 0.73111 (11) 0.0947 (9)
O2 0.4799 (2) 0.4492 (4) 0.71423 (9) 0.0695 (6)

1 Source of material

Ethyl 4-(4-benzylpiperazin-1-yl)benzoate was prepared by the direct reaction between 1-benzylpiperazine hydrochloride and ethyl 4-fluorobenzoate. In detail, a solution of ethyl 4-fluorobenzoate (17.51 g, 0.104 mol) and 1-benzylpiperazine hydrochloride (44.3 g, 0.209 mol) in N,N-dimethylformamide (100 ml) was stirred and refluxed at 433 K for 16 h. The reaction mixture was allowed to reach room temperature and poured into 750 ml stirring water. The solid part was filtered off, washed with water, dried for 15 h at 32 K in vacuo, recrystallized with 150 ml isopropanol, filtered off, washed with isopropanol and dried for 48 h at 323 K in vacuo, producing 23.5 g of ethyl 4-(4-benzylpiperazin-1-yl)benzoate in 69.7 % yield.

2 Experimental details

Single crystals of ethyl 4-(4-benzylpiperazin-1-yl)benzoate were cultured in a mixed solvent of dichloromethane and methol (20:1, v/v) for 3 days. Using Olex2, 1 the structure was solved with the ShelXT 2 structure solution program and refined with the ShelXL 3 refinement package. All hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

3 Comment

Ethyl 4-(4-benzylpiperazin-1-yl)benzoate is a key inermediate for the synthesis of diacylglycerol acyltransferase (DGAT) inhibitors, in particular a DGAT1 inhibitor. 4 DGAT is a microsomal enzyme that can be classified into four types based on structural and localization differences: DGAT1, DGAT2, bifunctional enzyme (wax ester synthase, WS/DGAT), and cytosolic DGAT (CytoDGAT). 5 Piperidine or piperazine derivatives exhibiting inhibitory activity against DGAT, particularly DGAT1. 6 Here, ethyl 4-(4-benzylpiperazin-1-yl)benzoate is the main starting material for the synthesis of piperazine derivatives. In the molecules forming the title crystal structure, the key bond lengths and angles are within normal ranges. The C–N bonds are confirmed by the distance of N1–C7, N2–C12. Their lengths are 1.469(3) Å, and 1.391(3) Å, respectively. Additionally, the lengths of C18–O1 and C18–O2 are 1.201(3) Å and 1.334(4) Å, which are consistent with the ester group. The bond angles of C8–N1–C11 and C9–N2–C10 measures 107.78(18) Å and 111.39(19) Å, respectively, which is attributed to the bond angles characteristic of piperazine. These results indicated the structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate.

Corresponding author: Yuanjiao Feng, Chongqing Medical and Pharmaceutical College, Chongqing, 404100, China, E-mail:

  1. Author contributions: Xue Zeng drafted most parts of the manuscript and conducted the experiments of crystal analysis. Wenwu Zhong and Yuanfang Hou cultured the crystal of compound. Yuanjiao Feng contributed to the analysis of results. All authors agreed to the final version of the manuscript. All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Chongqing Municipal Health Commission Traditional Chinese Medicine Scientific Research Project (2022MSXM213). Chongqing Education Commission Natural Science Foundation (KJZD-K202402802).

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

References

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2. Sheldrick, G. M. SHELXTL – Integrated Space-Group and Crystal-Structure Determination. Acta Crystallogr. 2015, A71, 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

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. Qi, J.; Lang, W.; Geisler, J. G.; Wang, P.; Petrounia, I.; Mai, S.; Smith, C.; Askari, H.; Struble, G. T.; Williams, R.; Bhanot, S.; Monia, B. P.; Bayoumy, S.; Grant, E.; Caldwell, G. W.; Todd, M. J.; Liang, Y.; Gaul, M. D.; Demarest, K. T.; Connelly, M. A. The Use of Stable Isotope-Labeled Glycerol and Oleic Acid to Differentiate the Hepatic Functions of DGAT1 and -2. J. Lipid Res., 2012, 53, 1106–1116. https://doi.org/10.1194/jlr.M020156.Search in Google Scholar PubMed PubMed Central

5. Chen, G.; Harwood, J. L.; Lemieux, M. J.; Stone, S. J.; Weselake, R. J. Acyl–CoA: Diacylglycerol Acyltransferase: Properties, Physiological Roles, Metabolic Engineering and Intentional Control. Prog. Lipid Res. 2022, 88, 101181; https://doi.org/10.1016/j.plipres.2022.101181.Search in Google Scholar PubMed

6. Okuma, C.; Ohta, T.; Tadaki, H.; Ishigure, T.; Sakata, S.; Taniuchi, H.; Sano, R.; Hamada, H.; Kume, S.; Nishiu, J.; Kakutani, M. JTP-103237, a Monoacylglycerol Acyltransferase Inhibitor, Prevents Fatty Liver and Suppresses Both Triglyceride Synthesis and De Novo Lipogenesis. J. Pharmacol. Sci. 2015, 128, 150–157; https://doi.org/10.1016/j.jphs.2015.06.007.Search in Google Scholar PubMed

Received: 2024-10-12
Accepted: 2024-11-13
Published Online: 2024-11-26
Published in Print: 2025-02-25

© 2024 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 the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
  8. Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
  9. The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
  10. The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
  11. The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
  15. The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
  16. Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
  17. The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
  20. The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
  21. Crystal structure of (−)-flavesine H, C15H22N2O2
  22. Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
  23. Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
  25. The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
  26. Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
  27. The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
  30. Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
  31. Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
  32. Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
  33. Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
  34. Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
  35. Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
  36. The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
  37. The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
  38. Crystal structure of diaqua-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II) dinitrate dihydrate, C60H76Cl8N14O14Zn
  39. The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
  40. Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
  41. Crystal structure of CaPtZn
  42. Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
  43. The crystal structure of (3′-(2-bromophenyl)-2-phenyl-[2,2′-bioxiran]-3-yl)(phenyl)methanone, C92H68O12Br4
  44. Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
  45. The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
  46. Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
  47. The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
  48. Crystal structure of 1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione, C17H12O2
  49. Crystal structure of (E)-2,2′,3,3′-tetrahydro-[1,1′-biindenylidene]-4,4′-diol, C18H16O2
  50. Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
  51. Crystal structure of {[(4-fluorophenyl)methyl]triphenylphosphonium}dibromocopper(I), [C25H21FP]+[CuBr2]−
  52. Crystal structure of poly[diaqua-bis(μ2-5-((pyridin-4-yl-methyl)amino)benzene-1,3-dicarboxylato-κ 2 N:O)cadmium(II)], C28H26CdN4O10
https://doi.org/10.1515/ncrs-2024-0405
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
  8. Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
  9. The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
  10. The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
  11. The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
  15. The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
  16. Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
  17. The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
  20. The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
  21. Crystal structure of (−)-flavesine H, C15H22N2O2
  22. Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
  23. Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
  25. The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
  26. Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
  27. The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
  30. Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
  31. Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
  32. Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
  33. Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
  34. Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
  35. Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
  36. The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
  37. The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
  38. Crystal structure of diaqua-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II) dinitrate dihydrate, C60H76Cl8N14O14Zn
  39. The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
  40. Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
  41. Crystal structure of CaPtZn
  42. Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
  43. The crystal structure of (3′-(2-bromophenyl)-2-phenyl-[2,2′-bioxiran]-3-yl)(phenyl)methanone, C92H68O12Br4
  44. Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
  45. The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
  46. Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
  47. The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
  48. Crystal structure of 1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione, C17H12O2
  49. Crystal structure of (E)-2,2′,3,3′-tetrahydro-[1,1′-biindenylidene]-4,4′-diol, C18H16O2
  50. Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
  51. Crystal structure of {[(4-fluorophenyl)methyl]triphenylphosphonium}dibromocopper(I), [C25H21FP]+[CuBr2]−
  52. Crystal structure of poly[diaqua-bis(μ2-5-((pyridin-4-yl-methyl)amino)benzene-1,3-dicarboxylato-κ 2 N:O)cadmium(II)], C28H26CdN4O10
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