Startseite Crystal structure of tert-butyl (phenylsulfinyl)carbamate, C11H15NO3S
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Crystal structure of tert-butyl (phenylsulfinyl)carbamate, C11H15NO3S

  • Parameshwar Makam , Marivel Samipillai , Hendrick G. Kruger , Thavendran Govender und Tricia Naicker EMAIL logo
Veröffentlicht/Copyright: 10. Mai 2017
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 232 Heft 4

Abstract

C11H15NO3S, orthorhombic, Pna21 (no. 33), a = 9.5337(10) Å, b = 10.7168(11) Å, c = 11.5675(11) Å, V = 1181.9(2) Å3, Z = 4, Rgt(F) = 0.0252, wRref(F2) = 0.0689, T = 173 K.

CCDC no.:: 1510979

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Colourless rod
Size:0.35 × 0.22 × 0.13 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:2.7 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:51°, >99%
N(hkl)measured, N(hkl)unique, Rint:6515, 2182, 0.030
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2165
N(param)refined:147
Programs:Bruker programs [1, 2] , SHELX [3], ORTEP-3 [4]
Table 2

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

AtomxyzUiso*/Ueq
C10.9431(2)0.0504(2)1.01470(19)0.0143(5)
C20.8834(2)−0.0146(2)1.1060(2)0.0174(5)
H20.7995840.0145661.1413480.021*
C30.9480(3)−0.1230(2)1.1451(2)0.0204(5)
H30.908463−0.1683811.2076480.024*
C41.0706(2)−0.1653(2)1.0926(2)0.0208(5)
H41.114818−0.2391371.1196610.025*
C51.1280(2)−0.0996(2)1.0011(2)0.0188(5)
H51.211468−0.1289580.9655040.023*
C61.0650(2)0.0084(2)0.9609(2)0.0165(4)
H61.1041660.0530320.8977660.020*
C70.9550(2)0.3748(2)0.86506(19)0.0132(4)
C81.0808(2)0.5492(2)0.7767(2)0.0164(5)
C90.9718(2)0.6497(2)0.7992(2)0.0221(5)
H9A0.9808670.7155840.7408760.033*
H9B0.8777920.6131030.7948080.033*
H9C0.9865750.6852500.8762570.033*
C101.0704(3)0.4934(2)0.6563(2)0.0219(5)
H10A1.0791510.5598020.5985400.033*
H10B1.1458640.4324060.6452980.033*
H10C0.9794510.4518440.6473700.033*
C111.2279(2)0.5987(2)0.7986(2)0.0225(5)
H11A1.2481030.6664690.7442000.034*
H11B1.2342580.6302020.8779200.034*
H11C1.2961010.5312870.7876750.034*
N10.97629(18)0.27716(16)0.94124(16)0.0139(4)
H11.0550260.2684120.9801180.017*
O11.06762(15)0.44860(15)0.86515(14)0.0156(4)
O20.84904(14)0.38734(16)0.80861(15)0.0178(4)
O30.74651(15)0.21720(15)1.04930(13)0.0161(4)
S10.84269(5)0.17653(4)0.95484(5)0.01270(18)

Source of material

The title compound was prepared from benzenesulfinamide according to the literature procedure [5]. In a round bottom flask, benzenesulfinamide 3 (0.40 g, 2.80 mmol) was dissolved in dry THF (12 mL) and cooled to −78 °C. After stirring the mixture for 10 min at −78 °C, n-butyl lithium (2.80 mL, 7.10 mmol) was added dropwise over 10 min. The mixture was stirred for 10 more minutes at −78 °C, followed by rapid addition of di-tert-butyl dicarbonate (0.742 g, 3.40 mmol), stirring was continued for 10 min at −78°C which gradually raised the temperature to RT and stirred overnight at room temperature. A saturated solution of NaHCO3 was then added and diluted with dichloromethane. The water phase was extracted with dichloromethane, dried over MgSO4, filtered, and concentrated under reduced pressure. Flash chromatography using dichloromethane as eluent yielded the title compound (0.306 g, 45%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.49 (s, 1H), 7.68–7.66 (m, 2H), 7.59–7.56 (m, 3H), 1.44 (s, 9H). 13C NMR (125 MHz, DMSO-d6) δ ppm 153.40, 143.49, 131.26, 128.97, 124.93, 81.47, 27.75. The title compound (10 mg) was dissolved in acetonitrile in a vial by sonication for 3 min. The vial was covered with parafilm with a tiny outlet to enable evaporate ion. Crystals suitable for X-ray diffraction formed over the period of 5 days.

Experimental details

The data were scaled and absorption correction performed using SADABS [1]. The structure was solved by direct methods using SHELXS-97 [3]. All hydrogen atoms were placed in idealised positions and refined in riding models with Uiso assigned the values to be 1.2 or 1.5 times those of their parent atoms and the constraint distances of CH ranging from 0.95 Å to 1.00 Å.

Discussion

Bioisosterism is an advantageous approach in medicinal chemistry, which facilitates the greater selectivity for a determined receptor or enzymatic isoform subtype. It can result in less side effects, decreased toxicity, improved solubility-hydrophobicity and different/better metabolic stability [6, 7] . Sulphur isosters viz. sulfines, sulfoximines, sulfonimidamides, sulfonamides, are the compounds of much interest in pharamceutical chemistry [8]. Sulfonamides are found to be an integral part of more than hundred approved drugs or molecules in clinical trials. Sulfonimidamide is an isostere of sulphonamide, which is formed by replacing one of the O-atoms by nitrogen of sulfonamide. The title compound can be considered as a potential pecursor for the preparation of sulfonimidamids [9], [10], [11], [12]. However crystal structures of sulfinylcarbamate derivatives are rare.

Crystal structure of the title compound shows that the sulfinyl (S=O) group is perpendicular to the amide bond of the molecule as it is observed in the crystal structures of most of the sulfonylcarbamate derivatives. The major interactions among molecules in the crystal structure of the title compound are established by N—H⋯O=S hydrogen bonds [d(N⋯O) = 2.864 Å] formed by sulfinyl and amide groups. From the CSD analysis it was noticed that this type of interactions occured only in a few cases of sulfonyl derivatives, while in most of the cases the major interactions among molecules in the crystals were established through the amide groups. In addition to N—H⋯O hydrogen bonds, the C—H⋯O secondary interactions formed by the carbonyl (C=O) and aromatic H-atoms are also involved in connecting adjacent molecules forming hydrogen bonded 1D tape-like arrangment running along [100] and such tapes are connected through various very weak C—H⋯O and C—H⋯π interactions.

References

1 Bruker. SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, WI, USA (2004).Suche in Google Scholar

2 Bruker. XPREP (version 5.1/NT). Bruker AXS Inc., Madison, WI, USA (1997).Suche in Google Scholar

3 Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

4 Farrugia, L. J.: ORTEP-3 for Windows − a version of ORTEP-III with a Graphical User Interface. J. Appl. Crystallogr. 30 (1997) 565–565.10.1107/S0021889897003117Suche in Google Scholar

5 Funes, M.; Sehgelmeble, F.; Bjarnemark, F.; Svensson, M.; Åhman, J.; Arvidsson, P. I.: Synthesis and arylation of unprotected sulfonimidamides. Tetrahedron 68 (2012) 7456–7462.10.1016/j.tet.2012.06.072Suche in Google Scholar

6 Patani, G. A.; LaVoie, E. J.: Bioisosterism: a rational approach in drug design. Chem. Rev. 96 (1996) 3147–3176.10.1021/cr950066qSuche in Google Scholar PubMed

7 Lima, L. M.; Barreiro, E. J.: Bioisosterism: a useful strategy for molecular modification and drug design. Curr. Med. Chem. 12 (2005) 23–49.10.2174/0929867053363540Suche in Google Scholar PubMed

8 Lücking, U.: Sulfoximines: a neglected opportunity in medicinal chemistry. Angew. Chem. Int. Ed. 52 (2013) 9399–9408.10.1002/anie.201302209Suche in Google Scholar PubMed

9 Borhade, S. R.; Svensson, R.; Brandt, P.; Artursson, P.; Arvidsson, P. I.; Sandström, A.: Preclinical characterization of acyl sulfonimidamides: potential carboxylic acid bioisosteres with tunable properties. ChemMedChem 10 (2015) 455–460.10.1002/cmdc.201402497Suche in Google Scholar PubMed

10 Nandi, G. C.; Kota, S. R.; Naicker, T.; Govender, T.; Kruger, H. G.; Arvidsson, P. I.: Cu(OAc)2-catalysed oxidative dual C–H/N–H activation of terminal alkynes and N-deprotected sulfonimidamides: an easy access to N-alkynylated sulfonimidamides. Eur. J. Org. Chem. 2015 (2015) 2861–2867.10.1002/ejoc.201500239Suche in Google Scholar

11 Pemberton, N.; Graden, H.; Evertsson, E.; Bratt, E.; Lepistö, M.; Johannesson, P.; Svensson, P. H.: Synthesis and functionalization of cyclic sulfonimidamides: a novel chiral heterocyclic carboxylic acid bioisostere. ACS Med. Chem. Lett. 3 (2012) 574–578.10.1021/ml3000935Suche in Google Scholar PubMed PubMed Central

12 Sehgelmeble, F.; Janson, J.; Ray, C.; Rosqvist, S.; Gustavsson, S.; Nilsson, L. I.; Minidis, A.; Holenz, J.; Rotticci, D.; Lundkvist, J.; Arvidsson, P. I.: Sulfonimidamides as sulfonamides bioisosteres: rational evaluation through synthetic, in vitro, and in vivo studies with γ-secretase inhibitors. ChemMedChem 7 (2012) 396–399.10.1002/cmdc.201200014Suche in Google Scholar PubMed

Received: 2016-11-2
Accepted: 2017-4-21
Published Online: 2017-5-10
Published in Print: 2017-7-26

©2017 Parameshwar Makam et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)manganese(II)] bis(4-chlorobenzenesulfonate) – 4,4′-bipyridine – water (1/1/2) C42H40Cl2MnN6O10S2
  3. The crystal structure of 1,2-bis[2-methyl-5-(3-cyanophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H16F6N2S2
  4. Crystal structure of the first characterized polymeric copper and sodium complex diaqua-(tris-acetato-κO,O′)(μ2-acetato-κO′′)dinatrium copper(II) monohydrate, C8H18CuNa2O11
  5. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-3-yl-methylene)aniline, C18H22N2
  6. Crystal structure of methyl 2,7,7-trimethyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C20H22N2O5
  7. Crystal structure of bis(1,3-bis(diphenylphosphino)propane-κ2P,P′)silver(I) trifluorosulfonate–methanol (1:0.5), [Ag(C27H26P2)]SO3CF3⋅0.5CH3OH
  8. Crystal structure of μ-1,4-bis(diphenylphosphine)butane-2,9-dimethyl-1,10-phenanthroline-κ2N:N′-bis(cyano-κC)dicopper(I)]-water, C58H56Cu2N6O2P2
  9. Crystal structure of N2,N6-bis(1-hydrazinyl-2-methyl-1-oxopropan-2-yl) pyridine-2,6-dicarboxamide, C15H23N7O4
  10. Crystal structure of 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide, C19H17IN2
  11. Crystal structure of diaqua-(2,2′-(butane-1,4-diyl)-bis(5-carboxy-1H-imidazole-4-carboxylato)-κ4O,O′,N,N′)cadmium(II) monohydrate, C14H18O11N4Cd
  12. Crystal structure of ethyl (E)-3-(cyclopropylamino)-2-(2,4-dichloro-5-fluorobenzoyl) acrylate, C15H14Cl2FNO3
  13. Crystal structure of bis-(1-(4-chlorophenyl)-3-phenyl-4-thenoyl-1H-pyrazol-5-ol-κ2O,O′)-(N,N-dimethylformamide)zinc(II), C43H31Cl2N5O5S2Zn
  14. Crystal structure of tetrakis(μ3-2-(N-(2-hydroxyethyl)amino)ethoxo)-tetrachloro-tetra-cobalt(II) methanol solvate, C17H44Cl4Co4N4O9
  15. Crystal structure of 3-amino-1-(4-bromophenyl)-9-methoxy-1H-benzo[f]chromene-2-carbonitrile, C21H15BrN2O2
  16. Crystal structure of 2-amino-4-(4-isopropyl-phenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene, C22H18N2O3
  17. Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C22H18N2O3
  18. Crystal structure of monoaqua-[6,6′-((1E,1′E)-(1,2-phenylene bis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-nitrophenolato-κ4N,N′,O,O′)]zinc(II), C20H12Br2N4O7Zn
  19. Crystal structure of 11-(4-(dimethylamino)phenyl)-17-hydroxy-13-methyl-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one – acetonitril (1/2), C33H41N3O2
  20. Crystal structure of tert-butyl (phenylsulfinyl)carbamate, C11H15NO3S
  21. Crystal structure of catena-poly{diaqua-bis(3-(1H-1,2,4-triazol-1-yl)benzoato-κ2O:N)copper(II)} monohydrate, C18H18CuN6O7
  22. Crystal structure of tetraaqua-bis(3-(4H-1,2,4-triazol-4-yl)benzoato-κN)cobalt(II), C18H20CoN6O8
  23. The crystal structure of 4-bromo-N-cyclopropyl-2,5-difluorobenzenesulfonamide, C9H8BrF2NO2S
  24. Crystal structure of ([3,3′-bipyridine]-6,6′-dicarboxylato-κ2O:O′)-bis(1,2-bis(4-pyridyl)ethane-κ2N:N′)disilver(I) dihydrate, C37H35Ag2N5O6
  25. The crystal structure of (4-(1H-1,2,4-triazol-1-yl)benzoato-κN)-[4-(1H-1,2,4-triazol-1-yl)benzoic acid-κN]silver(I), C18H13AgN6O4
  26. Crystal structure of 3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one, C17H16O2
  27. Crystal structure of bis(2-((E)-((4-((E)-1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-methoxyphenolato-κ2O,N)copper(II), C36H38CuN4O6
  28. Crystal structure of poly[1,2-bis(1,2,4-triazol-4-yl)ethane-κ2N:N′]silver(I) bromate monohydrate]silver(I), C6H10AgBrN6O4
  29. The crystal structure of 2,3,5-triphenyl-2,3-dihydro-1H-tetrazol-1-ium 2,3-dioxoindoline-5-sulfonate, C27H19N5O5S
  30. Crystal structure of 3-(2-amino-1,3-selenazol-4-yl)-2H-chromen-2-one – dimethylformamide (1/1), C15H15N3O3Se
  31. Crystal structure of diethyl 3,3′-(diazene-1,2-diyl)(E)-dibenzoate, C18H18N2O4
  32. Crystal structure of cis-bis((1H-benzimidazol-2-yl)methanol-κN,O)-bis(isothiocyanato-κN)nickel(II), C18H16N6NiO2S2
  33. Crystal structure of bis(2-(2′-hydroxy-5′-methoxyphenyl)-1H-benzimidazole)boron – tetrahydrofuran (1/1), C36H37N4O6B
  34. Crystal structure of poly[aqua-bis(nitrato-κ2O,O′)-(μ3-1,3-benzimidazol-3-ium-1,3-diacetato-κ4O,O′:O′′:O′′′)dysprosium(III)], C11H11DyN4O11
  35. Crystal structure of n-butyl-tris(dicyclo-hexylamido)hafnium(IV), C40H75HfN3
  36. Crystal structure of (E)-1-[1-(3-chloro-4-fluoro-phenyl)ethylidene]-2-(2,4-dinitrophenyl)hydrazine, C28H20Cl2F2N8O8
  37. The crystal structure of ethyl 4-((2-hydroxybenzyl)amino)benzoate, a Schiff base, C16H17NO3
  38. Crystal structure of 3-(2-(4-isobutylphenyl)propanoyl)-1-methylimidazolidine-2,4-dione, C17H22N2O3
  39. Crystal structure of poly[(μ3-2-(pyrazin-2-ylthio)acetato-κ3N:O:S)silver(I)], C6H5AgN2O2S
  40. Crystal structure of (E)-1-(3-((E)-((2-hydroxynaphthalen-1-yl)methylene)amino)phenyl)ethanone O-benzyl oxime, C26H22N2O2
  41. Crystal structure of (E)-2,3-dihydroxybenzaldehyde O-(2-((((E)-1-(2,5-dihydroxyphenyl)ethylidene)amino)oxy)ethyl) oxime monohydrate, C17H20N2O7
  42. Crystal structure of 4-(chloromethyl)-3-nitrobenzoic acid, C8H6ClNO4
  43. Crystal stucture of 4-((10H-phenothiazin-10-yl)methyl)-2,6-di-tert-butylphenol, C27H31NOS
  44. The crystal structure of ethyl 1-(4-nitrophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C13H10F3N3O4
  45. Crystal structure of catena-poly[di-(μ3-oxido-κ3O:O:O)-tetraoxido-(μ2-5′-(pyrazin-2-yl)-1H,2′H-3,3′-bi(1,2,4-triazole)-κ2N:N′)dimolybdenum(VI)], C8H6Mo2N8O6
  46. Crystal structure of (3,6-dioxocyclohexa-1,4-diene-1,4-bis(olato)-κ4O,O′:O′′,O′′′)-bis(tris(2-pyridylmethyl)amine-κ4N,N′,N′′,N′′′))-dizinc(II) bis(hexafluorophosphate(V)), C42H38F12N8O4P2Zn2
  47. Crystal structure of catena-poly[hexakis(μ2-2-acetylphenolato-κ3O:O,O′)trimanganese(II)], C48H42Mn3O12
  48. The crystal structure of 2,2-difluoro-4-(trifluoromethyl)-2,5-dihydro-[1,3,2]dioxaborinino[5,4-c]chromen-3-ium-2-uide, C11H6BF5O3
  49. Crystal structure of methyl (E)-2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazine-1-carboxylate, C13H19N3O3
  50. The crystal structure of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate, C10H15N3O2
  51. Crystal structure of 1,1-bis(η5-adamantylcyclopentadienyl)-3-phenyl-2-trimethylsilyl-2,3-dihydroisotitanazole, C42H55NSiTi
  52. Crystal structure of 2-(4-(2-(4-benzylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C28H29N3O2
  53. Important impurity of Flupirtine – a single crystal study on ethyl (6-amino-5-((ethoxycarbonyl)amino)pyridin-2-yl)(4-fluorobenzyl)carbamate, C18H21FN4O4
  54. Crystal structure of ethyl 3-(4-methoxyphenyl)-1-(2-(4-methoxyphenyl)-2-oxoethyl)-1H-pyrazole-5-carboxylate, C22H22N2O5
  55. Crystal structure of 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate methanol solvate, C37H35N1O10
  56. The crystal structure of the inner salt of 2-[(aminoiminomethyl)amino]ethylcarbamic acid [systematic name: (2-((diaminomethylene)ammonio)ethyl)carbamate], C4H10N4O2
  57. Crystal structure of (8-hydroxy-5-nitroquinolinium) perchlorate – 8-hydroxy-5-nitroquinoline (1/1), C18H13ClN4O10
  58. The crystal structure of (5-methyl-1,2,4-oxadiazol-3-yl)ferrocene, C13H12FeN2O
  59. Crystal structure of methyl 1-(2-(fluorosulfonyl)ethyl)-2-oxocyclopentanecarboxylate, C9H13FO5S
  60. Crystal structure of the triclinic modification of 1-methyl-4-nitroimidzole, C4H5N3O2
  61. Corrigendum
  62. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
https://doi.org/10.1515/ncrs-2016-0345
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Artikel in diesem Heft

  1. Cover and Frontmatter
  2. Crystal structure of poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)manganese(II)] bis(4-chlorobenzenesulfonate) – 4,4′-bipyridine – water (1/1/2) C42H40Cl2MnN6O10S2
  3. The crystal structure of 1,2-bis[2-methyl-5-(3-cyanophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H16F6N2S2
  4. Crystal structure of the first characterized polymeric copper and sodium complex diaqua-(tris-acetato-κO,O′)(μ2-acetato-κO′′)dinatrium copper(II) monohydrate, C8H18CuNa2O11
  5. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-3-yl-methylene)aniline, C18H22N2
  6. Crystal structure of methyl 2,7,7-trimethyl-4-(4-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C20H22N2O5
  7. Crystal structure of bis(1,3-bis(diphenylphosphino)propane-κ2P,P′)silver(I) trifluorosulfonate–methanol (1:0.5), [Ag(C27H26P2)]SO3CF3⋅0.5CH3OH
  8. Crystal structure of μ-1,4-bis(diphenylphosphine)butane-2,9-dimethyl-1,10-phenanthroline-κ2N:N′-bis(cyano-κC)dicopper(I)]-water, C58H56Cu2N6O2P2
  9. Crystal structure of N2,N6-bis(1-hydrazinyl-2-methyl-1-oxopropan-2-yl) pyridine-2,6-dicarboxamide, C15H23N7O4
  10. Crystal structure of 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide, C19H17IN2
  11. Crystal structure of diaqua-(2,2′-(butane-1,4-diyl)-bis(5-carboxy-1H-imidazole-4-carboxylato)-κ4O,O′,N,N′)cadmium(II) monohydrate, C14H18O11N4Cd
  12. Crystal structure of ethyl (E)-3-(cyclopropylamino)-2-(2,4-dichloro-5-fluorobenzoyl) acrylate, C15H14Cl2FNO3
  13. Crystal structure of bis-(1-(4-chlorophenyl)-3-phenyl-4-thenoyl-1H-pyrazol-5-ol-κ2O,O′)-(N,N-dimethylformamide)zinc(II), C43H31Cl2N5O5S2Zn
  14. Crystal structure of tetrakis(μ3-2-(N-(2-hydroxyethyl)amino)ethoxo)-tetrachloro-tetra-cobalt(II) methanol solvate, C17H44Cl4Co4N4O9
  15. Crystal structure of 3-amino-1-(4-bromophenyl)-9-methoxy-1H-benzo[f]chromene-2-carbonitrile, C21H15BrN2O2
  16. Crystal structure of 2-amino-4-(4-isopropyl-phenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2-c]chromene, C22H18N2O3
  17. Crystal structure of 3-amino-8-methoxy-1-(4-methoxy phenyl)-1H-benzo[f]chromene-2-carbonitrile, C22H18N2O3
  18. Crystal structure of monoaqua-[6,6′-((1E,1′E)-(1,2-phenylene bis(azanylylidene))bis(methanylylidene))bis(4-bromo-2-nitrophenolato-κ4N,N′,O,O′)]zinc(II), C20H12Br2N4O7Zn
  19. Crystal structure of 11-(4-(dimethylamino)phenyl)-17-hydroxy-13-methyl-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one – acetonitril (1/2), C33H41N3O2
  20. Crystal structure of tert-butyl (phenylsulfinyl)carbamate, C11H15NO3S
  21. Crystal structure of catena-poly{diaqua-bis(3-(1H-1,2,4-triazol-1-yl)benzoato-κ2O:N)copper(II)} monohydrate, C18H18CuN6O7
  22. Crystal structure of tetraaqua-bis(3-(4H-1,2,4-triazol-4-yl)benzoato-κN)cobalt(II), C18H20CoN6O8
  23. The crystal structure of 4-bromo-N-cyclopropyl-2,5-difluorobenzenesulfonamide, C9H8BrF2NO2S
  24. Crystal structure of ([3,3′-bipyridine]-6,6′-dicarboxylato-κ2O:O′)-bis(1,2-bis(4-pyridyl)ethane-κ2N:N′)disilver(I) dihydrate, C37H35Ag2N5O6
  25. The crystal structure of (4-(1H-1,2,4-triazol-1-yl)benzoato-κN)-[4-(1H-1,2,4-triazol-1-yl)benzoic acid-κN]silver(I), C18H13AgN6O4
  26. Crystal structure of 3-(4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one, C17H16O2
  27. Crystal structure of bis(2-((E)-((4-((E)-1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-methoxyphenolato-κ2O,N)copper(II), C36H38CuN4O6
  28. Crystal structure of poly[1,2-bis(1,2,4-triazol-4-yl)ethane-κ2N:N′]silver(I) bromate monohydrate]silver(I), C6H10AgBrN6O4
  29. The crystal structure of 2,3,5-triphenyl-2,3-dihydro-1H-tetrazol-1-ium 2,3-dioxoindoline-5-sulfonate, C27H19N5O5S
  30. Crystal structure of 3-(2-amino-1,3-selenazol-4-yl)-2H-chromen-2-one – dimethylformamide (1/1), C15H15N3O3Se
  31. Crystal structure of diethyl 3,3′-(diazene-1,2-diyl)(E)-dibenzoate, C18H18N2O4
  32. Crystal structure of cis-bis((1H-benzimidazol-2-yl)methanol-κN,O)-bis(isothiocyanato-κN)nickel(II), C18H16N6NiO2S2
  33. Crystal structure of bis(2-(2′-hydroxy-5′-methoxyphenyl)-1H-benzimidazole)boron – tetrahydrofuran (1/1), C36H37N4O6B
  34. Crystal structure of poly[aqua-bis(nitrato-κ2O,O′)-(μ3-1,3-benzimidazol-3-ium-1,3-diacetato-κ4O,O′:O′′:O′′′)dysprosium(III)], C11H11DyN4O11
  35. Crystal structure of n-butyl-tris(dicyclo-hexylamido)hafnium(IV), C40H75HfN3
  36. Crystal structure of (E)-1-[1-(3-chloro-4-fluoro-phenyl)ethylidene]-2-(2,4-dinitrophenyl)hydrazine, C28H20Cl2F2N8O8
  37. The crystal structure of ethyl 4-((2-hydroxybenzyl)amino)benzoate, a Schiff base, C16H17NO3
  38. Crystal structure of 3-(2-(4-isobutylphenyl)propanoyl)-1-methylimidazolidine-2,4-dione, C17H22N2O3
  39. Crystal structure of poly[(μ3-2-(pyrazin-2-ylthio)acetato-κ3N:O:S)silver(I)], C6H5AgN2O2S
  40. Crystal structure of (E)-1-(3-((E)-((2-hydroxynaphthalen-1-yl)methylene)amino)phenyl)ethanone O-benzyl oxime, C26H22N2O2
  41. Crystal structure of (E)-2,3-dihydroxybenzaldehyde O-(2-((((E)-1-(2,5-dihydroxyphenyl)ethylidene)amino)oxy)ethyl) oxime monohydrate, C17H20N2O7
  42. Crystal structure of 4-(chloromethyl)-3-nitrobenzoic acid, C8H6ClNO4
  43. Crystal stucture of 4-((10H-phenothiazin-10-yl)methyl)-2,6-di-tert-butylphenol, C27H31NOS
  44. The crystal structure of ethyl 1-(4-nitrophenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C13H10F3N3O4
  45. Crystal structure of catena-poly[di-(μ3-oxido-κ3O:O:O)-tetraoxido-(μ2-5′-(pyrazin-2-yl)-1H,2′H-3,3′-bi(1,2,4-triazole)-κ2N:N′)dimolybdenum(VI)], C8H6Mo2N8O6
  46. Crystal structure of (3,6-dioxocyclohexa-1,4-diene-1,4-bis(olato)-κ4O,O′:O′′,O′′′)-bis(tris(2-pyridylmethyl)amine-κ4N,N′,N′′,N′′′))-dizinc(II) bis(hexafluorophosphate(V)), C42H38F12N8O4P2Zn2
  47. Crystal structure of catena-poly[hexakis(μ2-2-acetylphenolato-κ3O:O,O′)trimanganese(II)], C48H42Mn3O12
  48. The crystal structure of 2,2-difluoro-4-(trifluoromethyl)-2,5-dihydro-[1,3,2]dioxaborinino[5,4-c]chromen-3-ium-2-uide, C11H6BF5O3
  49. Crystal structure of methyl (E)-2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazine-1-carboxylate, C13H19N3O3
  50. The crystal structure of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate, C10H15N3O2
  51. Crystal structure of 1,1-bis(η5-adamantylcyclopentadienyl)-3-phenyl-2-trimethylsilyl-2,3-dihydroisotitanazole, C42H55NSiTi
  52. Crystal structure of 2-(4-(2-(4-benzylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C28H29N3O2
  53. Important impurity of Flupirtine – a single crystal study on ethyl (6-amino-5-((ethoxycarbonyl)amino)pyridin-2-yl)(4-fluorobenzyl)carbamate, C18H21FN4O4
  54. Crystal structure of ethyl 3-(4-methoxyphenyl)-1-(2-(4-methoxyphenyl)-2-oxoethyl)-1H-pyrazole-5-carboxylate, C22H22N2O5
  55. Crystal structure of 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate methanol solvate, C37H35N1O10
  56. The crystal structure of the inner salt of 2-[(aminoiminomethyl)amino]ethylcarbamic acid [systematic name: (2-((diaminomethylene)ammonio)ethyl)carbamate], C4H10N4O2
  57. Crystal structure of (8-hydroxy-5-nitroquinolinium) perchlorate – 8-hydroxy-5-nitroquinoline (1/1), C18H13ClN4O10
  58. The crystal structure of (5-methyl-1,2,4-oxadiazol-3-yl)ferrocene, C13H12FeN2O
  59. Crystal structure of methyl 1-(2-(fluorosulfonyl)ethyl)-2-oxocyclopentanecarboxylate, C9H13FO5S
  60. Crystal structure of the triclinic modification of 1-methyl-4-nitroimidzole, C4H5N3O2
  61. Corrigendum
  62. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
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Heruntergeladen am 22.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2016-0345/html
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