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The crystal structure of alogliptinium meta-chlorobenzoate

  • Yu-Heng Ma , Wen-Jing Ma ORCID logo , Kang Yang , Kai-Yue Zhang , Qiao Zhang , Qing Hu , Wu-Guang Shan and Yi-Hong Wang EMAIL logo
Published/Copyright: September 30, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 6

Abstract

C18H22N5O2·C7H4ClO2, orthorhombic, P212121 (no. 19), a = 8.9188(2) Å, b = 10.8391(2) Å, c = 25.9295(5) Å, V = 2506.65(9) Å3, Z = 4, Rgt (F) = 0.0357, wRref (F 2) = 0.1085, T = 293(2) K.

CCDC No.: 2239925

The asymmetric unit of the title crystal structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.40 × 0.37 × 0.34 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 1.69 mm−1
Diffractometer, scan mode: XtaLAB Synergy, ω
θ max, completeness: 66.6°, >99 %
N(hkl)measured, N(hkl)unique, R int: 9419, 4279, 0.030
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3,898
N(param)refined: 345
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 0.4242 (5) 0.3274 (4) 0.61808 (18) 0.0819 (12)
H1 0.356699 0.331259 0.645366 0.092 (15)*
C2 0.4866 (6) 0.2165 (5) 0.60452 (18) 0.0834 (13)
H2 0.461870 0.144956 0.622404 0.107 (17)*
C3 0.5853 (5) 0.2126 (4) 0.56450 (16) 0.0734 (11)
C4 0.6237 (5) 0.3166 (3) 0.53667 (13) 0.0596 (8)
H4 0.691428 0.311803 0.509462 0.064 (11)*
C5 0.5591 (3) 0.4282 (3) 0.55022 (12) 0.0480 (7)
C6 0.4610 (4) 0.4332 (4) 0.59151 (14) 0.0623 (9)
H6 0.419743 0.508365 0.601383 0.061 (10)*
C7 0.5989 (3) 0.5440 (3) 0.52018 (11) 0.0457 (7)
C8 0.6868 (3) 0.7879 (3) 0.40523 (11) 0.0438 (6)
H8 0.722457 0.833441 0.374962 0.045 (8)*
C9 0.6339 (3) 0.8781 (3) 0.44572 (12) 0.0507 (7)
H9A 0.713274 0.936255 0.453619 0.073 (12)*
H9B 0.608320 0.834164 0.477108 0.053 (9)*
C10 0.4980 (4) 0.9464 (3) 0.42574 (15) 0.0571 (8)
H10A 0.527196 0.997257 0.396661 0.069 (11)*
H10B 0.460027 1.000352 0.452563 0.077 (12)*
C11 0.3747 (3) 0.8585 (3) 0.40907 (12) 0.0486 (7)
H11A 0.340059 0.811016 0.438441 0.059 (10)*
H11B 0.290492 0.904859 0.395451 0.055 (10)*
C12 0.5605 (3) 0.7018 (3) 0.38933 (11) 0.0406 (6)
H12A 0.595794 0.645176 0.363022 0.050 (9)*
H12B 0.527746 0.653794 0.418827 0.040 (8)*
C13 0.1842 (3) 0.6917 (3) 0.35628 (12) 0.0478 (7)
H13 0.148083 0.733416 0.385056 0.062 (10)*
C14 0.3290 (3) 0.7069 (3) 0.34216 (10) 0.0400 (6)
C15 0.2948 (3) 0.5670 (3) 0.27001 (11) 0.0459 (7)
C16 0.0863 (3) 0.6137 (3) 0.32818 (12) 0.0483 (7)
C17 0.0600 (5) 0.4575 (4) 0.25911 (17) 0.0749 (12)
H17A 0.001306 0.410487 0.283138 0.13 (2)*
H17B 0.125139 0.403179 0.240340 0.111 (18)*
H17C −0.005501 0.499233 0.235456 0.18 (3)*
C18 0.5177 (3) 0.6949 (3) 0.27054 (11) 0.0472 (7)
H18A 0.585385 0.625800 0.265709 0.057 (10)*
H18B 0.567829 0.755230 0.292111 0.060 (10)*
C19 0.3731 (4) 0.8412 (3) 0.21402 (14) 0.0523 (7)
H19 0.317810 0.864387 0.242845 0.057 (10)*
C20 0.4830 (3) 0.7520 (3) 0.21886 (11) 0.0421 (6)
C21 0.5651 (4) 0.7196 (3) 0.17514 (12) 0.0499 (7)
C22 0.6770 (4) 0.6253 (4) 0.17892 (13) 0.0620 (9)
C23 0.5358 (5) 0.7757 (4) 0.12763 (13) 0.0633 (9)
H23 0.590925 0.753546 0.098627 0.083 (13)*
C24 0.4254 (5) 0.8637 (3) 0.12391 (15) 0.0653 (9)
H24 0.405663 0.901208 0.092371 0.078 (12)*
C25 0.3439 (4) 0.8963 (3) 0.16700 (15) 0.0604 (9)
H25 0.269062 0.955735 0.164427 0.077 (12)*
Cl1 0.6700 (2) 0.07193 (10) 0.54875 (5) 0.1116 (5)
N1 0.8120 (3) 0.7110 (3) 0.42644 (9) 0.0462 (6)
H1A 0.855664 0.669541 0.400878 0.053 (9)*
H1B 0.775610 0.657951 0.449457 0.078 (13)*
H1C 0.879245 0.759691 0.441569 0.085 (14)*
N2 0.4340 (3) 0.7750 (2) 0.36911 (9) 0.0415 (5)
N3 0.1499 (3) 0.5485 (3) 0.28718 (10) 0.0512 (6)
N4 0.3806 (2) 0.6516 (2) 0.29682 (9) 0.0428 (5)
N5 0.7643 (5) 0.5491 (4) 0.18345 (15) 0.0922 (12)
O1 0.5343 (3) 0.6422 (2) 0.53142 (10) 0.0608 (6)
O2 0.6970 (3) 0.5325 (2) 0.48583 (8) 0.0557 (6)
O3 0.3449 (3) 0.5131 (2) 0.23236 (9) 0.0588 (6)
O4 −0.0470 (2) 0.5948 (3) 0.33937 (10) 0.0645 (7)

1 Source of material

All chemicals were purchased from commercial sources and used as received. The alogliptin (33.9 mg, 0.1 mol) and m chlorobenzoic acid (15.6 mg, 0.1 mol) were dissolved in MeOH (10 mL). The mixture was refluxed for 0.5 h and then filtered and placed in a sample vial, covered with membrane and punctured. The filtrate was slowly evaporated at room temperature to obtain crystals of the title compound.

2 Experimental details

X-ray intensity data of the crystal of dimensions 0.40 × 0.37 × 0.34 mm were collected on Rigaku HyPix detector diffractometer. Using Olex2, 1 the structure was solved with the XT 2 structure solution program and refined with the ShelXL 3 refinement package. All H atoms were positioned geometrically and treated as riding on their parent atoms, with the d(C–H) = 0.93 Å and d(N–H) = 0.89 Å, U iso(H) = 1.2 times U iso(C) and U iso(H) = 1.5 times U iso(O).

3 Comment

Alogliptin is a novel dipeptide peptidase-4 inhibitor approved for the treatment of type 2 diabetic mellitus. 4 Because of its low water solubility, alogliptin was commercialized orally in its benzoate salt form (Nesina), which was developed by Takeda Pharmaceutical Co., LTD. and has been approved for marketing in the United States in January 2013. 5 , 6 Salt formation is one of the most common used methods to improve the solubility and dissolution rates of insoluble drugs. 7

The asymmetric unit of the title structure contains one alogliptin cation and one m chlorobenzoic acid anion (see the figure). Bond lengths and angles are all in the expected ranges. The title molecule has an approximately ladder-like structure. 8 It indicates that three types of hydrogen bonds play an important role in maintaining the crystal structure, including, N1–H1A⋯O4 (1 + X, +Y, +Z) [length 2.875(3) Å, angle 173.5°], N1–H1B⋯O2 [length 2.677(3) Å, angle 169.4°], N1–H1C⋯O1 (1/2 + X, 3/2 – Y, 1 − Z) [length 2.768(3) Å, angle 174.5°]. 9 The carboxylate group forms two hydrogen bonds by interacting with an aminium group of alogliptinium in the unit cell and in an expanded unit cell. Another hydrogen bond comes from the additionally interacting between carbonyl group of alogliptin and an aminium group of another alogliptinium in an expanded unit cell. There are no specific interactions formed by the Cl atoms.

Corresponding author: Yi-Hong Wang, School of Chemistry and Chemical Engineering, Southeast University, Nanjing, Jiangsu, 211189, P.R. China, E-mail:

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

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

  3. Research funding: New engineering research and reform practice project (2021xgk10); Chuzhou University college students innovation and entrepreneurship training program (No. 2024CXXL021); Anhui University Natural Science Foundation (No. KJ2021B16).

References

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

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

4. Feng, J.; Zhang, Z.; Wallace, M. B.; Stafford, J. A.; Kaldor, S. W.; Kassel, D. B.; Navre, M.; Shi, L.; Skene, R. J.; Asakawa, T.; Takeuchi, K.; Xu, R.; Webb, D. R.; Gwaltney, S. L. Discovery of Alogliptin: A Potent, Selective, Bioavailable, and Efficacious Inhibitor of Dipeptidyl Peptidase IV. J. Med. Chem. 2007, 50, 2297–2300; https://doi.org/10.1021/jm070104l.Search in Google Scholar PubMed

5. Gelbrich, T.; Kahlenberg, V.; Griesser, U. J. Alogliptin and Its Benzoate Salt. J. Acta Crystallogr. 2013, 69, 674–678; https://doi.org/10.1107/s0108270113012560.Search in Google Scholar

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7. Serajudidin, A. T. M. Salt Formation to Improve Drug Delivery. Adv. Drug Deliv. Rev. 2007, 59, 613–616.10.1016/j.addr.2007.05.010Search in Google Scholar PubMed

8. James, T. P. M.; Sebusi, O.; Ofentse, M.; Lebogang, G. J.; Thuto, M.; Florence, N. Synthesis and Crystal Structure of Pyridin-4-Ylmethyl 4-Aminobenzoate, C13H12N2O2. Crystallogr. Rep. 2022, 67, 1203–1206; https://doi.org/10.1134/s1063774522070094.Search in Google Scholar

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Received: 2024-07-05
Accepted: 2024-09-16
Published Online: 2024-09-30
Published in Print: 2024-12-17

© 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 3-nitrophenol-2,1,3-benzoselenadiazole (1/1), C12H9N3O3Se
  4. Crystal structure of diaqua-(hydroxido)-{μ-[2-(hydroxy)-5-[(4-nitrophenyl)diazenyl]benzoato]}-{2-hydroxy-5-[(4-nitrophenyl)diazenyl]benzoato}-(1,10-phenanthroline)-diterbium hydrate, C38H27.4N8O12.2Tb
  5. Crystal structure of poly[bis(μ3-3-fluoro-4-(1H-1,2,4-triazol-1-yl)benzoato-κ3 O:O′:N)cadmium(II)] – dimethylformamide (1/1), C21H17CdF2N7O5
  6. The crystal structure of 2-amino-N-(pyridin-2-yl)benzamide, C12H11N3O
  7. The crystal structure of 2,3-di(pyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one, C18H14N4O
  8. Crystal structure of 2-chloro-4-fluorobenzyl (R)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18ClFO3
  9. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid]-(methylsulfinyl)methane, C15H16N2O6S
  10. The crystal structure of 2-ethyl-1,1-dimethyl-1H-benzo[e]indole, C16H17N
  11. The crystal structure of (Z)-5-amino-N ′-hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  12. The crystal structure of 2,2,5-trimethyl-3-(4-(4-(5-phenyl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)phenyl)imidazolidin-4-one, C24H24N4O2S
  13. The crystal structure of tetrakis(μ2-acetato-κ2 O:O′)-bis[(4′-phenyl-4,2′:6′,4″-terpyridine-κ1 N)dicopper(II)], C25H21CuN3O4
  14. Crystal structure of poly(3-thiophenecarboxylato-κ 3 O,O′:O′)-(methanol-κO)cadmium(II), C11H10O5S2Cd
  15. The crystal structure of dichloridobis[4′-(p-methoxylphenyl)-4,2′:6′,4″-terpyridine-κN] zinc(II), C44H34Cl2N6O2Zn
  16. The crystal structure of 1-(2-carboxyethyl)-1H-imidazole 3-oxide
  17. Crystal structure of 1,1′,1″-(nitrilotris(ethane-2,1-diyl))tris(3-(4-(((E)-pyridin-2-ylmethylene)amino)phenyl)urea), C45H47N13O4
  18. Crystal structure of a (E)-4-bromo-N-(4-(diethylamino)-2-hydroxybenzylidene) benzenaminium acetate ─ 4-bromoaniline (1/1)
  19. Crystal structure of 2,2′-(iminobis(methylene))bis(benzimidazolium) bis(p-toluenesulfonate), C30H31N5O6S2
  20. The crystal structure of alogliptinium meta-chlorobenzoate
  21. Crystal structure of 4-bromobenzyl 2-(6-methoxy-naphthalen-2-yl)propanoate, C21H19BrO3
  22. The hydrated double salt structure of (E)-4-(2-benzylidenehydrazine-1-carbonyl)pyridin-1-ium cation with 2-hydroxybenzoate and benzoate anions
  23. Crystal structure of (R)(R)-5-chloro-3-((S,1E,3E)-3,5-dimethyl-hepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-2,6,7,8-tetrahydroisoquinolin-7-yl acetate, C21H24ClNO4
  24. The crystal structure of bis(3-oxo-1,3-diphenylprop-1-en-1-olato-κ 2 O:O′)-bis(1,4-dioxane-κ 1 O)nickel(II), C38H38O8Ni
  25. Crystal structure of poly[aqua-(pyridine-3-carboxylato-κ1 N)(pyridine-3-carboxylato-κ2 O,O′) cadmium(II)] dihydrate, C12H14N2O7Cd
  26. The crystal structure of 4-(4-phenyl-5-(((1-(2,4,6-tribromophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-4H-1,2,4-triazol-3-yl)pyridine, C22H14Br3N7S
  27. The crystal structure of N-benzylquinoline-2-carbothioamide, C17H14N2S
  28. Crystal structure of bis(3-isopropylphenyl)-4,4′-bipyridinium dichloride dihydrate, C28H30N2⋅2Cl⋅2H2O
  29. The crystal structure of ethyl 2-amino-4-(cyanophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C19H18N2O4
  30. Crystal structure of (4R,10S)-6-hydroxy-7-isopropyl-4,10-dimethyl-1,2,3,5-hexahydro-6,10-epoxyazulen-9-one, C15H22O3
  31. The crystal structure of (E)-(2-(2-hydroxy-3-methoxybenzylidene)aminophenyl)arsonic acid, C14H14AsNO5
  32. The crystal structure of poly[(μ 2-2-aminoisophthalato-κ4O,O′:O″:O″′)-(N-methylpyrrolidone κ1O)-dioxido-uranium(VI)], C13H14N2O7U
  33. The crystal structure of the co-crystal isonicotinamide · terephthalic acid, C8H6O4·2(C6H6N2O)
  34. The crystal structure of (E)-1-phenyl-3-(p-tolylthio)but-2-en-1-one, C17H16OS
  35. The crystal structure of 4,5-bis((Z)-chloro(hydroxyimino)methyl)-1H-imidazol-3-ium chloride monohydrate
  36. The crystal structure of 1,2-bis(4-(dimethylamino)phenyl)ethane-1,2-dione. C18H20N2O2
  37. Crystal structure of 2-chloro-4-fluorobenzyl 2-acetoxybenzoate, C16H12ClFO4
  38. Crystal structure of methyl 1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate, C19H14N2O2
  39. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl)(5-fluoro-2-iodophenyl)methanone, C19H17FINO4
  40. Crystal structure of tetrachlorido-bis(1-[(1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2 N:N′)dicopper, C36H32Cu2N24Cl4
  41. Crystal structure of 2-(2,3-bis(4-methoxyphenyl)-1H-pyrrolo[2,3-b]quinoxalin-1-yl)anilin, C30H24N4O2
  42. Crystal structure of 5,7-dihydroxy-2-phenyl-4H-chromen-4-one–N,N-dimethylformamide(1/1), C18H17NO5
  43. The crystal structure of bis(μ 2-biphenyl-2,2′-dicarboxylato)-diaqua-bis(nitrato)-bis(2,2′:6′,2′′-terpyridine)dineodymium(III), C46H32I2N8Nd2O16
  44. Crystal structure of (Z)-4-amino-N ′-((4-chlorophenyl)(phenyl)methylene)benzohydrazide, C20H16ClN3O
  45. Crystal structure of (E)-6,8-dimethoxy-4-(4-morpholinobenzylidene)-3,4-dihydro-1-benzoxepin-5(2H)-one, C23H25NO5
  46. Crystal structure of (R)-2-((3-(3-aminopiperidin-1-yl)-6-methyl-5-oxo-1,2,4-triazin-4(5H)-yl) methyl)-4-fluorobenzonitrile benzoate monohydrate, C24H27FN6O4
  47. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylato-κ 3 N,O,O)copper(II)]monohydrate, C12H15NO9Cu
  48. Crystal structure of (((4-chlorophenyl)sulfonyl)glycinato-κ 2 N,O)bis(1,10-phenanthroline-κ 2 N,N′)cobalt(II) tetrahydrate, C32H30ClCoN5O8S
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  50. Crystal structure of 3-phenoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C27H24O4
  51. 6-(2′,3′-Dihydroxy-3′-methylbutyl)-7-methoxy-8-(3″-methylbut-2″-en-1″-yl)-2H-chromen-2-one, C20H26O5
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  54. Crystal structure of (1E,3E,5E)-1,6-bis(4-(pentyloxy)phenyl)hexa-1,3,5-triene, C28H36O2
  55. The crystal structure of tris(2-bromo-4-methylphenyl)amine, C21H18Br3N
  56. The crystal structure of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, C21H22N2O2
  57. Crystal structure of dicarbonyl (μ2-indole-2-carboxylato κ2 O:O′)tris(triphenylarsine-κAs)dirhodium(I) acetone solvate, C68H56As3NO5Rh2
  58. The crystal structure of 4-chloro-2-formylphenyl 4-methylbenzenesulfonate, C14H11ClO4S
  59. Crystal structure of 4-iodobenzyl 2-(6-methoxynaphthalen-2-yl) propanoate, C21H19IO3
https://doi.org/10.1515/ncrs-2024-0283
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of 3-nitrophenol-2,1,3-benzoselenadiazole (1/1), C12H9N3O3Se
  4. Crystal structure of diaqua-(hydroxido)-{μ-[2-(hydroxy)-5-[(4-nitrophenyl)diazenyl]benzoato]}-{2-hydroxy-5-[(4-nitrophenyl)diazenyl]benzoato}-(1,10-phenanthroline)-diterbium hydrate, C38H27.4N8O12.2Tb
  5. Crystal structure of poly[bis(μ3-3-fluoro-4-(1H-1,2,4-triazol-1-yl)benzoato-κ3 O:O′:N)cadmium(II)] – dimethylformamide (1/1), C21H17CdF2N7O5
  6. The crystal structure of 2-amino-N-(pyridin-2-yl)benzamide, C12H11N3O
  7. The crystal structure of 2,3-di(pyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one, C18H14N4O
  8. Crystal structure of 2-chloro-4-fluorobenzyl (R)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18ClFO3
  9. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid]-(methylsulfinyl)methane, C15H16N2O6S
  10. The crystal structure of 2-ethyl-1,1-dimethyl-1H-benzo[e]indole, C16H17N
  11. The crystal structure of (Z)-5-amino-N ′-hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  12. The crystal structure of 2,2,5-trimethyl-3-(4-(4-(5-phenyl-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)phenyl)imidazolidin-4-one, C24H24N4O2S
  13. The crystal structure of tetrakis(μ2-acetato-κ2 O:O′)-bis[(4′-phenyl-4,2′:6′,4″-terpyridine-κ1 N)dicopper(II)], C25H21CuN3O4
  14. Crystal structure of poly(3-thiophenecarboxylato-κ 3 O,O′:O′)-(methanol-κO)cadmium(II), C11H10O5S2Cd
  15. The crystal structure of dichloridobis[4′-(p-methoxylphenyl)-4,2′:6′,4″-terpyridine-κN] zinc(II), C44H34Cl2N6O2Zn
  16. The crystal structure of 1-(2-carboxyethyl)-1H-imidazole 3-oxide
  17. Crystal structure of 1,1′,1″-(nitrilotris(ethane-2,1-diyl))tris(3-(4-(((E)-pyridin-2-ylmethylene)amino)phenyl)urea), C45H47N13O4
  18. Crystal structure of a (E)-4-bromo-N-(4-(diethylamino)-2-hydroxybenzylidene) benzenaminium acetate ─ 4-bromoaniline (1/1)
  19. Crystal structure of 2,2′-(iminobis(methylene))bis(benzimidazolium) bis(p-toluenesulfonate), C30H31N5O6S2
  20. The crystal structure of alogliptinium meta-chlorobenzoate
  21. Crystal structure of 4-bromobenzyl 2-(6-methoxy-naphthalen-2-yl)propanoate, C21H19BrO3
  22. The hydrated double salt structure of (E)-4-(2-benzylidenehydrazine-1-carbonyl)pyridin-1-ium cation with 2-hydroxybenzoate and benzoate anions
  23. Crystal structure of (R)(R)-5-chloro-3-((S,1E,3E)-3,5-dimethyl-hepta-1,3-dien-1-yl)-7-methyl-6,8-dioxo-2,6,7,8-tetrahydroisoquinolin-7-yl acetate, C21H24ClNO4
  24. The crystal structure of bis(3-oxo-1,3-diphenylprop-1-en-1-olato-κ 2 O:O′)-bis(1,4-dioxane-κ 1 O)nickel(II), C38H38O8Ni
  25. Crystal structure of poly[aqua-(pyridine-3-carboxylato-κ1 N)(pyridine-3-carboxylato-κ2 O,O′) cadmium(II)] dihydrate, C12H14N2O7Cd
  26. The crystal structure of 4-(4-phenyl-5-(((1-(2,4,6-tribromophenyl)-1H-1,2,3-triazol-4-yl)methyl)thio)-4H-1,2,4-triazol-3-yl)pyridine, C22H14Br3N7S
  27. The crystal structure of N-benzylquinoline-2-carbothioamide, C17H14N2S
  28. Crystal structure of bis(3-isopropylphenyl)-4,4′-bipyridinium dichloride dihydrate, C28H30N2⋅2Cl⋅2H2O
  29. The crystal structure of ethyl 2-amino-4-(cyanophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C19H18N2O4
  30. Crystal structure of (4R,10S)-6-hydroxy-7-isopropyl-4,10-dimethyl-1,2,3,5-hexahydro-6,10-epoxyazulen-9-one, C15H22O3
  31. The crystal structure of (E)-(2-(2-hydroxy-3-methoxybenzylidene)aminophenyl)arsonic acid, C14H14AsNO5
  32. The crystal structure of poly[(μ 2-2-aminoisophthalato-κ4O,O′:O″:O″′)-(N-methylpyrrolidone κ1O)-dioxido-uranium(VI)], C13H14N2O7U
  33. The crystal structure of the co-crystal isonicotinamide · terephthalic acid, C8H6O4·2(C6H6N2O)
  34. The crystal structure of (E)-1-phenyl-3-(p-tolylthio)but-2-en-1-one, C17H16OS
  35. The crystal structure of 4,5-bis((Z)-chloro(hydroxyimino)methyl)-1H-imidazol-3-ium chloride monohydrate
  36. The crystal structure of 1,2-bis(4-(dimethylamino)phenyl)ethane-1,2-dione. C18H20N2O2
  37. Crystal structure of 2-chloro-4-fluorobenzyl 2-acetoxybenzoate, C16H12ClFO4
  38. Crystal structure of methyl 1-phenyl-9H-pyrido[3,4-b]indole-3-carboxylate, C19H14N2O2
  39. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl)(5-fluoro-2-iodophenyl)methanone, C19H17FINO4
  40. Crystal structure of tetrachlorido-bis(1-[(1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2 N:N′)dicopper, C36H32Cu2N24Cl4
  41. Crystal structure of 2-(2,3-bis(4-methoxyphenyl)-1H-pyrrolo[2,3-b]quinoxalin-1-yl)anilin, C30H24N4O2
  42. Crystal structure of 5,7-dihydroxy-2-phenyl-4H-chromen-4-one–N,N-dimethylformamide(1/1), C18H17NO5
  43. The crystal structure of bis(μ 2-biphenyl-2,2′-dicarboxylato)-diaqua-bis(nitrato)-bis(2,2′:6′,2′′-terpyridine)dineodymium(III), C46H32I2N8Nd2O16
  44. Crystal structure of (Z)-4-amino-N ′-((4-chlorophenyl)(phenyl)methylene)benzohydrazide, C20H16ClN3O
  45. Crystal structure of (E)-6,8-dimethoxy-4-(4-morpholinobenzylidene)-3,4-dihydro-1-benzoxepin-5(2H)-one, C23H25NO5
  46. Crystal structure of (R)-2-((3-(3-aminopiperidin-1-yl)-6-methyl-5-oxo-1,2,4-triazin-4(5H)-yl) methyl)-4-fluorobenzonitrile benzoate monohydrate, C24H27FN6O4
  47. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylato-κ 3 N,O,O)copper(II)]monohydrate, C12H15NO9Cu
  48. Crystal structure of (((4-chlorophenyl)sulfonyl)glycinato-κ 2 N,O)bis(1,10-phenanthroline-κ 2 N,N′)cobalt(II) tetrahydrate, C32H30ClCoN5O8S
  49. Crystal structure of (((3-nitrophenyl)sulfonyl)-β-alaninato-κO)bis(2,2′-bipyridine-κ 2 N, N′)copper(II) 3-nitrobenzenesulfonate, C35H29CuN7O11S2
  50. Crystal structure of 3-phenoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C27H24O4
  51. 6-(2′,3′-Dihydroxy-3′-methylbutyl)-7-methoxy-8-(3″-methylbut-2″-en-1″-yl)-2H-chromen-2-one, C20H26O5
  52. Crystal structure of bromido-(2,2′:6′,2″-terpyridine-4′-onato-κ3N)palladium(II) methanol solvate
  53. The crystal structure of ethyl 2-amino-(4-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C20H22N2O6
  54. Crystal structure of (1E,3E,5E)-1,6-bis(4-(pentyloxy)phenyl)hexa-1,3,5-triene, C28H36O2
  55. The crystal structure of tris(2-bromo-4-methylphenyl)amine, C21H18Br3N
  56. The crystal structure of 3-(2,5-dimethylanilino)-1-(2,5-dimethylphenyl)-4-methyl-1H-pyrrole-2,5-dione, C21H22N2O2
  57. Crystal structure of dicarbonyl (μ2-indole-2-carboxylato κ2 O:O′)tris(triphenylarsine-κAs)dirhodium(I) acetone solvate, C68H56As3NO5Rh2
  58. The crystal structure of 4-chloro-2-formylphenyl 4-methylbenzenesulfonate, C14H11ClO4S
  59. Crystal structure of 4-iodobenzyl 2-(6-methoxynaphthalen-2-yl) propanoate, C21H19IO3
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