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Crystal structure of S-(4-carboxybutyl)- l -cysteine

  • James K. Waters , Valeri V. Mossine ORCID logo EMAIL logo , Steven P. Kelley and Thomas P. Mawhinney
Published/Copyright: July 23, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 5

Abstract

C8H15NO4S, orthorhombic, P212121 (no. 19), a = 5.0215 (3) Å, b = 7.0392 (5) Å, c = 28.0593 (19) Å, V = 991.82 (11) Å3, Z = 4, R gt(F) = 0.0462, wR ref(F 2) = 0.0899, T = 100 K.

CCDC no.: 2367970

The molecular structure, hydrogen bonds, a part of the title crystal structure and the electrostatic energy framework are shown in the figure. Tables 1 and 2 contain details on the crystal structure as well as measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless plate
Size: 0.18 × 0.10 × 0.01 mm
Wavelength:

μ:		 Mo Kα radiation (0.71073 Å)

0.32 mm−1
Diffractometer, scan mode:

θ max, completeness:		 Bruker APEX II, φ and ω

29.0°, >99 %
N(hkl)measured, N(hkl)unique, R int: 13,433, 2638, 0.048
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2473
N(param)refined: 174
Programs: Bruker, 1 SHELX, 2 , 3 Olex2 4
Table 2:

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

Atom x y z U iso*/U eq
S1 0.45191 (15) 0.04882 (12) 0.12329 (2) 0.01319 (17)
O1 1.1723 (4) −0.0418 (4) 0.24142 (7) 0.0136 (4)
O2 0.7671 (4) −0.0568 (4) 0.27473 (7) 0.0134 (4)
C1 0.9256 (6) −0.0711 (4) 0.24029 (9) 0.0087 (5)
O3 0.8845 (4) −0.0766 (3) −0.11118 (7) 0.0165 (5)
O4 0.5098 (4) 0.0376 (4) −0.14442 (7) 0.0144 (5)
C5 0.5356 (7) 0.0382 (5) 0.02807 (10) 0.0139 (6)
H5A 0.345 (8) −0.003 (5) 0.0283 (12) 0.017*
H5B 0.547 (8) 0.177 (5) 0.0277 (12) 0.017*
C4 0.6598 (7) −0.0325 (5) 0.07451 (10) 0.0128 (6)
H4A 0.842 (7) 0.014 (5) 0.0795 (12) 0.015*
H4B 0.661 (8) −0.173 (5) 0.0759 (12) 0.015*
C7 0.5341 (7) 0.0446 (5) −0.06108 (9) 0.0141 (6)
H7A 0.341 (8) 0.011 (5) −0.0629 (12) 0.017*
H7B 0.534 (8) 0.183 (5) −0.0596 (12) 0.017*
C6 0.6665 (6) −0.0385 (5) −0.01705 (10) 0.0130 (6)
H6A 0.861 (7) −0.009 (5) −0.0169 (12) 0.016*
H6B 0.642 (7) −0.180 (5) −0.0183 (12) 0.016*
N1 0.5859 (5) −0.2606 (4) 0.19879 (9) 0.0088 (5)
C2 0.7987 (6) −0.1157 (4) 0.19187 (10) 0.0085 (5)
H2 0.928 (7) −0.169 (5) 0.1700 (11) 0.010*
C3 0.6849 (6) 0.0706 (5) 0.17204 (10) 0.0114 (6)
H3A 0.827 (7) 0.151 (5) 0.1641 (12) 0.014*
H3B 0.582 (7) 0.124 (5) 0.1962 (12) 0.014*
C8 0.6645 (6) −0.0048 (4) −0.10798 (10) 0.0105 (6)
H1A 0.461 (8) −0.207 (5) 0.2132 (12) 0.012 (9)*
H1B 0.657 (8) −0.362 (6) 0.2149 (14) 0.026 (11)*
H1C 0.524 (10) −0.301 (6) 0.1713 (16) 0.039*
H4 0.608 (9) 0.034 (7) −0.1716 (15) 0.039*

1 Source of materials

l–Cysteine (12.1 g, 0.1 mol) and 4-pentenoic acid (11 g, 0.11 mol) were dissolved in 500 mL of water containing 4.4 g (0.11 mol) of NaOH and left overnight at room temperature. The solution was further acidified with 6.6 mL (0.11 mol) of glacial acetic acid and allowed to stand at 4°C for next 3 days. Colourless plates of chromatographically pure crystalline CBC have formed during this time; the crystalline mass was filtered out, washed with cold 95 % ethanol, dried on air and used for subsequent diffraction studies. Element analysis. Calc. for C8H15NO4S: N, 6.33 %. Found: N, 6.37 %. Exact mass of the [M+H]+ ion in ESI mass-spectrum. Calc. for C6H12NO4S: m/z 222.07. Found: m/z 222.08.

2 Experimental details

The Flack absolute structure parameter determined (−0.02 (3) for 1277 quotients 5 ) is consistent with the (2R) configuration, which was assigned for this molecule on the basis of the known configuration for the starting material l-cysteine. Data were corrected for Lorentz, polarization, and absorption effects. The hydroxyl and ammonium hydrogen atoms were located in difference Fourier maps and were allowed to refine freely. The remaining H-atoms were placed at calculated positions and included in the refinement using a riding model. All hydrogen atom thermal parameters were constrained to ride on the carrier atoms (U iso(methine H) = 1.2 U eq and U iso(methyl H) = 1.5 U eq).

3 Comment

The title compound, S-(4-carboxybutyl)- l -cysteine (CBC), is a synthetic analog of two important biologically active S-carboxyalkylcysteines, a mucolytic drug S-carboxymethyl–l-cysteine (carbocisteine, CMC) and a natural insecticide from legumes S-(2-carboxyethyl)–l-cysteine (β–CEC). 6 Both CMC and β–CEC are thioether-containing amino acids and, similarly to methionine, possess the antioxidant capacity that could be employed in clinics. 7 Recently, 8 , 9 we have demonstrated that CMC and β–CEC can protect DNA from oxidative degradation, protect airway and kidney cells from cytotoxic platinum drugs or copper oxide nanoparticles, mitigate pro-inflammatory signaling in the cells. In continuation of our studies on antioxidant amino acids, 8 , 9 , 10 we have synthesized CBC and report here its molecular and crystal structure.

The asymmetric unit of the title structure contains one molecule of CBC, shown in the Figure generated by Mercury. 11 The valence bond lengths and angles are in the expected ranges. The molecule of this dicarboxylic amino acid exists as a zwitterion, with positively charged protonated α-amino group and negatively charged deprotonated α-carboxylic group. Most of non-hydrogen atoms, with exception of N1, O1, and C3, are located within 0.3 Å from a molecular plane. There is a weak intramolecular hydrogen bond between the ammonium donor and thioether acceptor heteroatoms (N1⃛S1 = 3.112 (3) Å, H1C⃛S1 = 2.83 (4) Å, N1–H1C⃛S1 = 101 (3)°). The conventional hydrogen bonding in crystal structure of CBC is extensive, involves all heteroatoms and forms network layers propagating in parallel to (001). Each layer is formed by a system of intercrossing chains. In the [100] direction, the heterodromic chain ⃛H1C–N1–H1B⃛O1–C1–O2⃛H4–O4–C8–O3⃛H1C–N1–H1B⃛ incorporates the shortest heteroatom contact formed between the α- and η-carboxylic groups (O4⃛O2 = 2.534 (3) Å, H4⃛O2 = 1.64 (4) Å, O4–H4⃛O2′ = 168 (4)°, ’ = 3/2−x, −y, −1/2 + z). In the [010] direction, the antidromic chains ⃛H1A–N1–H1B⃛O1⃛H1A–N1–H1B⃛O1⃛ feature bifurcated H-bonds at the O1 atoms. The network is reinforced by the short C3–H3A⃛O4 and C4–H4B⃛O3 contacts contributing to the polar interactions in the crystal structure, as well.

To account for all interactions contributing to the crystal structure, we have performed DFT calculations, at the B3LYP/6–31 G(d,p) theory level, 12 , 13 of the electrostatic, dispersion, polarization, and repulsion energies in the CBC crystal structure. According to the calculations, the interactions between pairs of molecules linked via the N1–H1B⃛O1″ hydrogen bond (” = 2−x, −1/2 + y, 1/2−z) provided the largest contribution, about 30 %, to the lattice energy, with the electrostatic interactions contributing the most for the attractive forces between neighbouring molecules of CBC (i.e. Eelstat = −90.3 kJ/mol, Eenergy-dispersive = −15 kJ/mol for 2 − x, −1/2 + y, 1/2 − z). The spatial distribution of the energetically most significant interactions is illustrated in the Figure, showing the electrostatic energy framework as red cylinders penetrating the crystal lattice of CBC. The cylinders connect centroids of the interacting molecules, and their diameters are proportional to the total energies of the interactions, with the 10 kJ/mol cut-off, for clarity. The most extensive intermolecular interactions occur in the directions parallel to [001]. To estimate the crystal structure energy, the total energies of unique pairwise interactions between molecules were integrated, thus yielding Ecryst = −353.5 kJ/mol for the CBC crystal.

Corresponding author: Valeri V. Mossine, Department of Biochemistry, University of Missouri, Columbia, MO 65211, USA, E-mail:

Funding source: University of Missouri Agriculture Experiment Station Chemical Laboratories and by the National Institute of Food and Agriculture

Award Identifier / Grant number: Hatch project 1023929

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

  2. Research funding: University of Missouri Agriculture Experiment Station Chemical Laboratories and by the National Institute of Food and Agriculture (Hatch project 1023929).

  3. Competing interests: The authors declare no conflicts of interest regarding this article.

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Received: 2024-06-03
Accepted: 2024-07-04
Published Online: 2024-07-23
Published in Print: 2024-10-28

© 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. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
  5. Hydrogen bonding and π⋅⋅⋅halogen interactions in the crystal structure of bis(theophyllinium) hexachloridoplatinate(IV) monohydrate
  6. The crystal structure of 6-amino-2-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O′:O″)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
  12. The crystal structure of 1,3,5-tri(1H-imidazol-1-yl)benzene–2,3,5,6-tetrachlorobenzene-1,4-dicarboxylic acid (1/1)
  13. Crystal structure of dichlorido-bis(1-[(2-ethyl-benzimidazole-1-yl)methyl]-1H–benzotriazole) cadmium(II), C32H32CdN10OCl2
  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
  15. Crystal stucture of 3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide
  16. Crystal structure of bis(μ-benzeneselenolato)-(tetracarbonyl)-{μ-[N-(diphenylphosphanyl)-N-(3-ethynylphenyl)-P,P-diphenylphosphinous amide]} diiron, C48H35Fe2NO4P2Se2
  17. The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
  20. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10
  21. Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2
  22. The crystal structure of (3-chlorothiophene-2-carboxylato-κ2O, O′)-(2,2′-dipyridyl-κ2N,N′)lead(II), C20H12Cl2N2O4S2Pb
  23. Synthesis and crystal structure of (Z)-4-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, C19H14FN5O
  24. The crystal structure of the coordination compound catena-poly[(18-crown-6-ether-κ6O6)(4,5-dinitroimidazolato-κ1O)potassium(I)]
  25. Crystal structure of 7-(diethylamino)-3-(trifluoroacetyl)-2H-chromen-2-one, C15H14F3NO3
  26. Crystal structure of dichlorido-1-[(2-ethylimidazole-1-yl)methyl]-1H–benzotriazole κ1N zinc(II), C24H26ZnN10Cl2
  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
  28. Crystal structure of catena-poly[bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-k3-O,O′:O″)hexaqua-dicobalt tetrahydrate], C26H36N4O20Co2
  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
  31. The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4
  32. Crystal structure of bis(benzyltrimethylammonium) tetrathiotungstate(VI), {(C6H5CH2)(CH3)3N}2[WS4]
  33. The crystal structure of ethyl (Z)-2-(ethoxymethylene)-3-oxobutanoate, C9H14O4
  34. The crystal structure of (E)-6-bromo-3,5-dimethyl-2-(1-phenylprop-1-en-2-yl)-3Himidazo[4,5b]pyridine, C17H16BrN3
  35. Crystal structure of (3S,3′S,4R,4′S)-3′-(furan-3-yl)-3-hydroxy-4′-methyl-3,5,6′,7′-tetrahydro-1H,3′H-4,5′-spirobi[isobenzofuran]-1,1′(4′H)-dione-methanol (1/1), C21H22O7
  36. Cocrystal structure of progesterone-isophthalic acid, C25H33O4
  37. The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C17H12FN3O
  38. Crystal structure of S-(4-carboxybutyl)- l -cysteine
  39. The cocrystal of 2,2′-(hydrazine-1,1-diyl)bis(1H-imidazole-4,5-dicarbonitrile)– methanol (2/3)
  40. Crystal structure of (1′R,2′S,4′R,6′S)-4,6-dihydroxy-1′,8′,8′-trimethyl-3-(3-methylbutanoyl)-4′,8′,6′,1′,7,2′-hexahydro-1H-4′,6′-methanoxanthene-8-carbaldehyde, C23H30O5
  41. Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P
  42. Crystal structure of 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide dimethyl sulfoxide monosolvate, C17H18N4O2S·C2H6OS
  43. Crystal structure of (S)-4-(2-(4-(2-acetyl-5-chlorophenyl)-3-methoxy-6-oxopyridazin-1(6H)-yl)-3-phenylpropanamido)benzoic acid monohydrate, C29H26ClN3O7
  44. The crystal structure of 1,3-bis(2,4-dinitro-1H-imidazol-1-yl)propane
  45. Crystal structure of 4-chlorobenzyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H19ClO3
  46. Crystal structure of 1-(5-(benzo[d][1,3]dioxol-5-yl)-4-benzyl-1-(4-bromophenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethan-1-one, C24H20BrN3O3
  47. The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5
  48. Crystal structure of (S)-1-phenylpropan-1-aminium (S)-(1-phenylpropyl)carbamate C19H26N2O2
  49. Synthesis and crystal structure of methyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, C18H16BrN3O2S
  50. The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]
  51. Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
  52. The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4
  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N′)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2′-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
https://doi.org/10.1515/ncrs-2024-0237
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Articles in the same Issue

  1. Frontmatter
  2. Editorial
  3. Editorial 2024 – New developments and changes of Zeitschrift für Kristallographie – New Crystal Structures
  4. New Crystal Structures
  5. Hydrogen bonding and π⋅⋅⋅halogen interactions in the crystal structure of bis(theophyllinium) hexachloridoplatinate(IV) monohydrate
  6. The crystal structure of 6-amino-2-carboxypyridin-1-ium perchlorate, C6H7ClN2O6
  7. Crystal structure of poly[(μ4-(3-amino-1H-1,2,4-triazol-1-yl)benzene-1,3-dicarboxylato-κ 4 N:O:O':O')(1-methylpyrroldin-2-one-κ1O)dicopper(II)] – 1-methylpyrroldin-2-one (1/3), C40H48Cu2N12O12
  8. The crystal structure of 18-crown-6-k6O6(2,4,5-trinitroimidazol-1-ido-k1O)potassium(I)
  9. Crystal structure of poly[tetraaqua-bis(μ2-5-bromoisophthalato-κ3O,O′:O″)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)dicadmium(II)] dihydrate
  10. Crystal structure of (5R,6S,E)-5-acetoxy-2-methyl-6-((2aR,3R,5aS,5bS,11aR,12aS)-2a,5a,8,8-tetramethyl-9-oxotetradecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-3-yl)hept-2-enoic acid, C32H48O5
  11. The crystal structure of poly[diaqua-bis(μ2 -thiocyanato-κ2N:O)cobalt(II) monohydrate
  12. The crystal structure of 1,3,5-tri(1H-imidazol-1-yl)benzene–2,3,5,6-tetrachlorobenzene-1,4-dicarboxylic acid (1/1)
  13. Crystal structure of dichlorido-bis(1-[(2-ethyl-benzimidazole-1-yl)methyl]-1H–benzotriazole) cadmium(II), C32H32CdN10OCl2
  14. The crystal structure of N′-(tert-butyl)-N′-(3,5-dimethylbenzoyl)-3-methoxy-N,2-dimethylbenzohydrazide, C23H30N2O3
  15. Crystal stucture of 3-benzamido-N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide
  16. Crystal structure of bis(μ-benzeneselenolato)-(tetracarbonyl)-{μ-[N-(diphenylphosphanyl)-N-(3-ethynylphenyl)-P,P-diphenylphosphinous amide]} diiron, C48H35Fe2NO4P2Se2
  17. The crystal structure of 2′-(p-tolyl)-4′H-spiro[isochromane-1,1′-naphthalene]-3,4′-dione, C25H18O3
  18. The crystal structure of poly[hexaqua-tetrakis(μ4-pyridine-2,4-dicarboxylate-κ5N: O: O′: O″: O‴)-bi(μ2-pyridine-2,4-dicarboxylate-κ3N: O: O′)-digadolinium(III)tricopper (II)], [Gd2Cu3(C7H3NO4)6(H2O)6] n
  19. Crystal structure of poly[bis(4-(4-(pyridin-4-yl)phenyl)pyridin-1-ium-κ1N)-(μ4-benzene-1,2,4,5-tetracarboxylato-κ5O:O′: O″:O‴:O⁗)-(μ2-2,5-dicarboxyterephthalato-κ2O:O′)dizinc(II)], C52H32N4O16Zn2
  20. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-carboxy-6-nitrobenzoate monohydrate, C24H25FN4O10
  21. Crystal structure of dichlorido-(1-((3,5-dimethyl-2,3-dihydro-1H-1,2,3-triazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-k1N)zinc(II), C22H24ZnN12Cl2
  22. The crystal structure of (3-chlorothiophene-2-carboxylato-κ2O, O′)-(2,2′-dipyridyl-κ2N,N′)lead(II), C20H12Cl2N2O4S2Pb
  23. Synthesis and crystal structure of (Z)-4-((1-(3-fluorophenyl)-1H-1,2,3-triazol-4-yl)methylene)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, C19H14FN5O
  24. The crystal structure of the coordination compound catena-poly[(18-crown-6-ether-κ6O6)(4,5-dinitroimidazolato-κ1O)potassium(I)]
  25. Crystal structure of 7-(diethylamino)-3-(trifluoroacetyl)-2H-chromen-2-one, C15H14F3NO3
  26. Crystal structure of dichlorido-1-[(2-ethylimidazole-1-yl)methyl]-1H–benzotriazole κ1N zinc(II), C24H26ZnN10Cl2
  27. Crystal and molecular structure of 5-bromopyridine-2,3-diamine
  28. Crystal structure of catena-poly[bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-k3-O,O′:O″)hexaqua-dicobalt tetrahydrate], C26H36N4O20Co2
  29. Crystal structure of thiocyanate-κ1N-bis(μ1-2,6-diformyl-4-methylphenol oxime-κ2N,O)-manganese(III) acetonitrile solvate, C21H21MnN6O6S
  30. The crystal structure of pyrrolidin-1-yl pivalate, C9H13NO4
  31. The crystal structure of 2,2′-(2,2-diphenylethene-1,1-diyl)bis(1,4-dimethoxybenzene), C30H28O4
  32. Crystal structure of bis(benzyltrimethylammonium) tetrathiotungstate(VI), {(C6H5CH2)(CH3)3N}2[WS4]
  33. The crystal structure of ethyl (Z)-2-(ethoxymethylene)-3-oxobutanoate, C9H14O4
  34. The crystal structure of (E)-6-bromo-3,5-dimethyl-2-(1-phenylprop-1-en-2-yl)-3Himidazo[4,5b]pyridine, C17H16BrN3
  35. Crystal structure of (3S,3′S,4R,4′S)-3′-(furan-3-yl)-3-hydroxy-4′-methyl-3,5,6′,7′-tetrahydro-1H,3′H-4,5′-spirobi[isobenzofuran]-1,1′(4′H)-dione-methanol (1/1), C21H22O7
  36. Cocrystal structure of progesterone-isophthalic acid, C25H33O4
  37. The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C17H12FN3O
  38. Crystal structure of S-(4-carboxybutyl)- l -cysteine
  39. The cocrystal of 2,2′-(hydrazine-1,1-diyl)bis(1H-imidazole-4,5-dicarbonitrile)– methanol (2/3)
  40. Crystal structure of (1′R,2′S,4′R,6′S)-4,6-dihydroxy-1′,8′,8′-trimethyl-3-(3-methylbutanoyl)-4′,8′,6′,1′,7,2′-hexahydro-1H-4′,6′-methanoxanthene-8-carbaldehyde, C23H30O5
  41. Crystal structure of (3,6-di(2-pyridyl)-4-methylphenyl pyridazine-k 2 N,N′)-bis(1-phenyl-pyrazole-κ 2 C,N) iridium(III) hexafluorophosphate, C39H29F6IrN8P
  42. Crystal structure of 1,5-bis[(E)-1-(2-hydroxyphenyl)ethylidene]thiocarbonohydrazide dimethyl sulfoxide monosolvate, C17H18N4O2S·C2H6OS
  43. Crystal structure of (S)-4-(2-(4-(2-acetyl-5-chlorophenyl)-3-methoxy-6-oxopyridazin-1(6H)-yl)-3-phenylpropanamido)benzoic acid monohydrate, C29H26ClN3O7
  44. The crystal structure of 1,3-bis(2,4-dinitro-1H-imidazol-1-yl)propane
  45. Crystal structure of 4-chlorobenzyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate, C21H19ClO3
  46. Crystal structure of 1-(5-(benzo[d][1,3]dioxol-5-yl)-4-benzyl-1-(4-bromophenyl)-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethan-1-one, C24H20BrN3O3
  47. The crystal structure of (Z)-3′-(2-(1-(3,4-dimethyl-phenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene)hydrazinyl)-2′-hydroxy-[1,1′-biphenyl]-3-carboxylicacid ─ methanol (1/1), C26H26N4O5
  48. Crystal structure of (S)-1-phenylpropan-1-aminium (S)-(1-phenylpropyl)carbamate C19H26N2O2
  49. Synthesis and crystal structure of methyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, C18H16BrN3O2S
  50. The crystal structure of trichlorobis(pyridine-2,6-dithio-κS-carbomethylamido)antimony(III), [SbCl3(C9H11N3S2)2]
  51. Crystal structure of 1,8-dihydroxy-3-{[(triphenylstannyl)oxy]carbonyl} anthracene-9,10-dione, C33H22O6Sn
  52. The crystal structure of (E)-4-(2-(pyridin-4-ylmethylene)hydrazine-1-carbonyl)pyridin-1-ium-2-olate dihydrate, C12H14N4O4
  53. The crystal structure of 6-amino-pyridinium-2-carboxylate, C6H6N2O2
  54. The crystal structure of catena-poly[aqua-nitrato-κ3O,O:O′′-(1,10-phenanthroline-κ2N,N′)sodium(I)], C24H18N6O7Na2
  55. Retractions
  56. Retraction of: Crystal structure of bis[diaquaisonicotinatosamarium(III)]-µ-isonicotinato-[diisonicotinatocopper(II)], CuSm2(C6H4NO2)8(H2O)4
  57. Retraction of: Crystal structure of aqua(2,2′-bipyridine-k 2 N:N′)(nitrato)-(4-aminobenzoato)cadmium(II) nitrate, [Cd(H2O)(NO3)(C10H8N2)(C7H7NO2)][NO3]
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