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Crystal structure of 1-ferrocenylsulfonyl-1H-imidazo[4,5-b]pyridine, C16H13FeN3O2S

  • Jing Hu , Lu-Yao Wang EMAIL logo , Xiao-Long Guo and Lu Li
Published/Copyright: March 13, 2017
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 232 Issue 3

Abstract

C16H13FeN3O2S, triclinic, P1̅, a = 8.1311(9) Å, b = 11.6852(13) Å, c = 17.044(2) Å, α = 102.754(6)°, β = 92.548(7)°, γ = 105.563(6)°, V = 1512.3(3) Å3, Z = 4, Rgt(F) = 0.0473, wRref(F2) = 0.1307, T = 296(2) K.

CCDC no.:: 1504597

One of two crystallographically independent complexes forming 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:Yellow block
Size:0.40 × 0.30 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:11.5 cm−1
Diffractometer, scan mode:Bruker P4, ω scans
2θmax, completeness:53°, 98.6%
N(hkl)measured, N(hkl)unique, Rint:19703, 6091, 0.041
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4666
N(param)refined:415
Programs:Bruker programs [1], SHELX [2]
Table 2

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

AtomxyzUiso*/Ueq
Fe11.19212(5)0.33355(4)0.31342(3)0.03820(14)
S10.85732(10)0.26505(7)0.41406(5)0.0435(2)
O10.9501(3)0.2775(2)0.48935(14)0.0568(6)
O20.7819(3)0.3565(2)0.40026(17)0.0612(7)
N10.6876(3)0.1392(2)0.40096(17)0.0448(6)
N20.4138(4)0.0219(3)0.3671(2)0.0569(7)
N30.8141(4)−0.0066(3)0.44394(17)0.0517(7)
C10.5207(4)0.1266(3)0.3703(2)0.0539(8)
H10.48910.18890.35340.065*
C20.6836(4)0.0263(3)0.41729(19)0.0433(7)
C30.7673(5)−0.1214(3)0.4535(2)0.0596(9)
H30.8525−0.15130.47230.072*
C40.6012(5)−0.1987(3)0.4372(2)0.0618(10)
H40.5789−0.27700.44590.074*
C50.4688(5)−0.1613(3)0.4086(2)0.0577(9)
H50.3566−0.21210.39760.069*
C60.5118(4)−0.0445(3)0.3970(2)0.0470(7)
C70.9712(4)0.2260(2)0.33508(18)0.0369(6)
C80.9489(4)0.2519(3)0.25767(19)0.0441(7)
H80.86790.29300.24090.053*
C91.0644(4)0.2047(3)0.2095(2)0.0498(8)
H91.08100.21070.15380.060*
C101.1568(4)0.1515(3)0.2568(2)0.0457(7)
H101.24830.11500.23900.055*
C111.1003(4)0.1630(2)0.33398(18)0.0383(6)
H111.14110.13350.37850.046*
C121.4413(5)0.4314(4)0.3124(3)0.0718(12)
H121.52830.39960.28430.086*
C131.4095(4)0.4305(3)0.3904(2)0.0576(9)
H131.46980.39790.42730.069*
C141.2767(5)0.4827(3)0.4085(3)0.0674(11)
H141.22880.49520.46040.081*
C151.2263(6)0.5165(3)0.3390(4)0.0885(17)
H151.13690.55720.33380.106*
C161.3287(8)0.4837(4)0.2791(3)0.0929(18)
H161.32430.49710.22440.112*
Fe20.85776(6)0.73437(4)0.19340(3)0.04590(15)
S20.75741(10)0.68109(7)−0.00391(5)0.04133(19)
O30.9231(3)0.7328(2)−0.02459(15)0.0556(6)
O40.6875(3)0.55166(19)−0.01933(14)0.0509(6)
N40.6176(3)0.7246(2)−0.05864(15)0.0422(6)
N50.3691(4)0.7106(3)−0.1282(2)0.0602(8)
N60.7571(4)0.9421(2)−0.04033(18)0.0521(7)
C170.4572(5)0.6530(3)−0.0947(2)0.0538(9)
H170.41550.5706−0.09490.065*
C180.4746(4)0.8305(3)−0.1124(2)0.0459(7)
C190.6296(4)0.8422(3)−0.06850(18)0.0398(7)
C200.7267(5)1.0416(3)−0.0581(2)0.0588(9)
H200.81091.1160−0.03970.071*
C210.5784(5)1.0408(3)−0.1020(3)0.0601(9)
H210.56671.1134−0.11220.072*
C220.4495(5)0.9348(3)−0.1303(2)0.0573(9)
H220.34970.9327−0.16010.069*
C230.7354(4)0.7501(3)0.09337(18)0.0393(6)
C240.6116(4)0.6974(3)0.14197(19)0.0446(7)
H240.52490.61750.12640.053*
C250.6383(5)0.7847(3)0.2164(2)0.0543(8)
H250.57500.77380.26310.065*
C260.7738(5)0.8874(3)0.2149(2)0.0548(9)
H260.81920.95960.26000.066*
C270.8367(4)0.8691(3)0.1389(2)0.0470(8)
H270.92980.92630.12050.056*
C281.0276(6)0.7610(5)0.2916(3)0.0795(12)
H281.04850.82970.33930.095*
C290.9091(7)0.6555(6)0.2829(4)0.0959(15)
H290.83240.63260.32320.115*
C300.9139(7)0.5808(4)0.2065(4)0.1039(18)
H300.84450.49600.18400.125*
C311.0497(8)0.6550(6)0.1685(3)0.0969(16)
H311.09100.63070.11600.116*
C321.1126(5)0.7639(4)0.2269(3)0.0721(11)
H321.20440.83430.22060.087*

Source of material

All reagents and solvents were purchased form commercial sources and used as received. The title compound is obtained from a reaction of 1H-imidazo[4,5-b]pyridine and ferrocenylsulfonyl chloride. A solution of 1H-imidazo[4,5-b]pyridine (0.32 g, 2.7 mmol) in acetonitrile (18 mL) was added to a mixture of ferrocenylsulfonylchloride (0.72 g, 2.5 mmol) and anhydrous sodium carbonate (0.26 g, 2.5 mmol) with constant stirring. The mixture was heated to reflux temperatures for 48 h. The acetonitrile was evaporated under vacuum to leave a brown solid. The crude product was purified by column chromatography (SiO2, petroleum ether) to give the title compound (0.41 g, 45% yield) in form of yellow crystals, mp: 473–474 K.

Experimental details

The crystal structure was solved by the direct method. Hydrogen atoms were positioned geometrically and allowed to ride on their respective parent atoms. C—H distances were set to 0.93 Å and their Uiso set to 1.2 times the Ueq for the atoms to which they are bonded.

Comment

Some imidazo[4,5-b]pyridines possess diverse pharmacological properties, including anticancer, antiviral, and other important biological activities [3], [4], [5]. The asymmetric unit of the title compound contains two 1-ferrocenylsulfonyl-1H-imidazo[4,5-b]pyridine complexes, which are very similar. There is an imidazo[4,5-b]pyridinyl and a ferrocenyl moiety in the structure. The imidazo[4,5-b]pyridinyl is almost planar in both independent complexes. There are small differences in bond lengths between the substituted and unsubstituted cyclopentadienyl ring [6, 7] . The five-membered rings of the ferrocenyl moieties are almost parallel to each other.

Acknowledgement

This work is financially supported by the Ministry of Education of Beijing’s University Key Teacher (2010).

References

1 Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA, (2013).Search in Google Scholar

2 Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

3 Rajesh, P. K.; Mohammad, U. S.; Ganesh, R. J.: Eco-friendly and facile synthesis of 2-substituted-1H-imidazo[4,5-b]pyridine in aqueous medium by air oxidation. Tetrahedron Lett. 50 (2009) 1780–1782.10.1016/j.tetlet.2008.12.104Search in Google Scholar

4 Ayyiliath, M. S.; Muralidharan, A.: Microwave enhanced Suzuki coupling: a diversity-oriented approach to the synthesis of highly functionalised 3-substituted-2-aryl/heteroaryl imidazo[4,5-b]pyridines. Tetrahedron Lett. 53 (2012) 1036–1041.10.1016/j.tetlet.2011.12.051Search in Google Scholar

5 Wang, L. Y.; Gao, Y.; Yang, B. Q.; Shi, Z.: Synthesis, structure and bioactivity of nitrobenzoimidazole derivatives. Chem. J. Chin. University 26 (2005) 2241–2246.Search in Google Scholar

6 Wang, L. Y.; Meng, D.: Crystal structure of 2-ethyl-1-ferrocenylsulfonyl-6-nitro-1H-1,3-benzimidazole, C19H17FeN3O4S. Z. Kristallogr. -NCS 228 (2013) 35–36.10.1524/ncrs.2013.0022Search in Google Scholar

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Received: 2016-9-16
Accepted: 2017-2-21
Published Online: 2017-3-13
Published in Print: 2017-5-24

©2017 Jing Hu et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 2,5-diiodo-4-nitro-1H-imidazole hemihydrate, C6H4I4N6O5
  3. Crystal structure of catena-poly[μ2-2,2′-(1,3-phenylene)diacetato-κ4O,O′:O′′,O′′′)-(μ2-1,6-bis(2-methyl-1H-benzo[d]imidazol-1-yl)hexane-κ2N:N′)cadmium(II)], C32H34CdN4O4
  4. Crystal structure of poly[aqua-(2,2′-bipyridine-κN,N′)-(μ4-5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalato κ8O1,O2:O3,O4:O5,O6:O7,O8)manganese(II)], C21H21MnN2O7
  5. Crystal structure of poly-[(μ2-((1,3-bis(benzimidazol-1-yl)propane-κ2N:N′)(μ2-4-tert-butyl-phthalato-κ2O:O′)cobalt(II)] monohydrate, C29H30CoN4O5
  6. Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-5-(oxo-5,6,7,8-tetrahydro-4H-chromene)-3-carbonitrile – ethanol (1/1), C21H26N2O6
  7. Crystal structure of ethyl 1-benzyl-5-phenyl-1H-pyrazole-3-carboxylate, C19H18N2O2
  8. Crystal structure of 2-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-5-(4-nitrobenzylthio)-1,3,4-oxadiazole, C25H19N5O3S
  9. Structure and photochromism of 1,2-bis[2-methyl-5-(2-chlorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16Cl2F6S2
  10. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene)aniline, C18H22N2
  11. Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino) methyl)phenol, C10H14Br2N2O3
  12. Crystal structure of (bis(2,2′-bipyridine-κ2N,N′))-(3,5-dinitrosalicylato-κ2O,O′)nickel(II), C27H18N6NiO7
  13. Crystal structure of 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol, C18H24ClO5P
  14. Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C22H27CuN4O12.50
  15. Crystal structure of 1α,11-dihydroxyeremophil-9-en-8-one, C15H24O3
  16. Crystal structure of 1-ferrocenylsulfonyl-1H-imidazo[4,5-b]pyridine, C16H13FeN3O2S
  17. Crystal structure of bis(μ2-azido-κ2N:N)-dichlorido-bis(μ2-2-(pyridin-2-yl)ethan-1-ol-κ2O,N)dicopper(II), C14H18Cl2Cu2N8O2
  18. Crystal structure of (5,15-cis-bis(2-hydroxy-1-naphthyl)-10-phenyl-20-(4-hydroxyphenyl)-porphyrinato)-(pyridine)-zinc(ii) pyridine solvate, C67H47N7O3Zn
  19. Crystal structure of (μ2-[2,2′-bis(diphenylphosphino)-1,1′-binaphthalene oxide-κ2O,P])-iodido copper(I), C44H32CuIOP2
  20. Crystal structure of 6,8-diphenyl-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(3H)-one, C27H20FNO
  21. Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4
  22. Crystal structure of N,N′–bis(pyridin-4-ylmethyl)pyrazine-2,3-dicarboxamide dihydrate, C18H20N6O4
  23. Crystal structure of a diaqua-bis(3,5-di(1H-imidazol-1-yl)pyridine-κN)-bis(2-(4-carboxy-phenyl)acetato-κO]manganese(II), C40H36MnN10O10
  24. Crystal structure of 4-(4-hydroxy-3-methoxy-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester, C21H25NO5
  25. Crystal structure of (E)-4,4′-(ethene-1,2-diyl)bis(3-nitrobenzoic acid) 1.5 hydrate, C16H13N2O9.5
  26. Crystal structure of (E)-2-(5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-5-((4-fluorophenyl)diazenyl)-4-methylthiazole, C23H17F2N5OS
  27. Crystal structure of the co-crystalline adduct 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide - acetic acid (1/1), C21H24N4O4S ⋅ C2H4O2
  28. Synthesis and crystal structure of 2-((5-chlorobenzo[c][1,2,5]thiadiazol-4-yl)amino)-4,5-dihydro-1H-imidazol-3-ium tetraphenylborate, C33H29BClN5S
  29. Crystal structure of (4-chlorophenyl)(3-ferrocenyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)methanone, C21H14ClF3FeN2O
  30. Crystal structure of (S)-benzyl 3-(benzylcarba-moyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, C25H24N2O3
  31. Crystal structure of 5-acetyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, C15H17FN2O4
  32. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16FIN2
  33. Crystal structure of methyl 1H-indole-2-carboxylate, C10H9NO2
  34. Crystal structure of 2,3-diphenyl-1-[(dipropylamino)acetyl]-1,3-diazaspiro[4.5]decan-4-one, C28H37N3O2
  35. Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3
  36. Crystal structure of 2,9-dibromo-1,10-phenanthroline, C12H6Br2N2
  37. Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S
  38. Crystal structure of trans-bis((E)-7-oxo-4-(phenyldiazenyl)cyclohepta-1,3,5-trien-1-olato)-κ2O,O′)-bis(pyridine-κN)cobalt(II), C36H28CoN6O4
  39. Crystal structure of 2-(4-methyl-3-phenylthiazol-2(3H)-ylidene)malononitrile, C13H9N3S
  40. Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S
  41. Crystal structure of chlorido{[3-(η5-cyclopenta-dienyl)-2,2,3-trimethyl-1-phenylbutylidene] azanido-κN}[η2(N,O)-N,N-dimethylhydroxylaminato]titanium(IV), C20H27ClN2OTi
  42. Crystal Structure of 1,1′-dimethyl-[4,4′-bipyridine]-1,1′-diium tetrachloridozincate(II), C12H14Cl4N2Zn
  43. Crystal structure of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde, C11H12N2O3
  44. Crystal structure of 2,3-diphenyl-1-(morpholin-4-ylacetyl)-1,3-diazaspiro[4.5]decan-4-one, C26H31N3O3
  45. Crystal structure of 3,3-dimethyl-3,4-dihydro-1H-benzo[c]chromene-1,6(2H)-dione, C15H14O3
  46. Crystal structure of bis(2-(2-hydroxymethyl)pyridine-κ2N,O)-bis(pivalato-κO)nickel(II), C22H32N2NiO6
  47. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II) trihydrate, C20H20N6O7Mn
  48. The crystal structure of 3-aminopropan-1-aminium iodide, C3H11N2I
  49. Crystal structure of ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4 carboxylate, C12H12ClN3O2
  50. Crystal structure of 4,4′-((1Z,1′Z)-2,2′-(2,5-diethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine, C24H24N2O2
  51. Crystal structure of (16S)-12,16-epoxy-11,14-dihydroxy-17(15/16)-abeo-3a,18-cyclo-8,11,13-abietatrien-7-one, C20H24O4
  52. Crystal structure of aquadichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N,N′,N′′)nickel(II) monohydrate, C18H16Cl2N6NiO2
  53. Crystal structure of catena-poly[dichlorido-(μ-ethane-1,2-diyl-bis-(pyridyl-4-carboxylate-κN:N′)mercury(II)], C15H14Cl2HgN2O4
  54. Crystal structure of methyl 2-acetamido-5-chlorbenzoate, C10H10ClNO3
  55. Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
  56. Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  57. Crystal structure of 4-(2-ammonioethyl)morpholin-4-ium dichloride monohydrate, C6H18Cl2N2O2
  58. Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
  59. Crystal structure of 2-(4-(dimethylamino)-2-fluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol monohydrate, C15H20FN7O2
  60. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
  61. Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16
https://doi.org/10.1515/ncrs-2016-0278
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 2,5-diiodo-4-nitro-1H-imidazole hemihydrate, C6H4I4N6O5
  3. Crystal structure of catena-poly[μ2-2,2′-(1,3-phenylene)diacetato-κ4O,O′:O′′,O′′′)-(μ2-1,6-bis(2-methyl-1H-benzo[d]imidazol-1-yl)hexane-κ2N:N′)cadmium(II)], C32H34CdN4O4
  4. Crystal structure of poly[aqua-(2,2′-bipyridine-κN,N′)-(μ4-5,5′-(hexane-1,6-diyl)-bis(oxy)diisophthalato κ8O1,O2:O3,O4:O5,O6:O7,O8)manganese(II)], C21H21MnN2O7
  5. Crystal structure of poly-[(μ2-((1,3-bis(benzimidazol-1-yl)propane-κ2N:N′)(μ2-4-tert-butyl-phthalato-κ2O:O′)cobalt(II)] monohydrate, C29H30CoN4O5
  6. Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-5-(oxo-5,6,7,8-tetrahydro-4H-chromene)-3-carbonitrile – ethanol (1/1), C21H26N2O6
  7. Crystal structure of ethyl 1-benzyl-5-phenyl-1H-pyrazole-3-carboxylate, C19H18N2O2
  8. Crystal structure of 2-(1-benzyl-3-phenyl-1H-pyrazol-5-yl)-5-(4-nitrobenzylthio)-1,3,4-oxadiazole, C25H19N5O3S
  9. Structure and photochromism of 1,2-bis[2-methyl-5-(2-chlorophenyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16Cl2F6S2
  10. The crystal structure of the Schiff base (E)-2,6-diisopropyl-N-(pyridin-4-ylmethylene)aniline, C18H22N2
  11. Crystal structure of (E)-2,4-dibromo-6-(((4-methyl-2-nitrophenyl)imino) methyl)phenol, C10H14Br2N2O3
  12. Crystal structure of (bis(2,2′-bipyridine-κ2N,N′))-(3,5-dinitrosalicylato-κ2O,O′)nickel(II), C27H18N6NiO7
  13. Crystal structure of 1-(diethoxy phosphonomethyl) 2-benzoyl-3-chloro-2-cyclohexen-1-ol, C18H24ClO5P
  14. Crystal structure of tetraaqua-bis(1,3-benzimidazol-3-ium-1,3-diacetato-κO)copper(II) hemihydrate, C22H27CuN4O12.50
  15. Crystal structure of 1α,11-dihydroxyeremophil-9-en-8-one, C15H24O3
  16. Crystal structure of 1-ferrocenylsulfonyl-1H-imidazo[4,5-b]pyridine, C16H13FeN3O2S
  17. Crystal structure of bis(μ2-azido-κ2N:N)-dichlorido-bis(μ2-2-(pyridin-2-yl)ethan-1-ol-κ2O,N)dicopper(II), C14H18Cl2Cu2N8O2
  18. Crystal structure of (5,15-cis-bis(2-hydroxy-1-naphthyl)-10-phenyl-20-(4-hydroxyphenyl)-porphyrinato)-(pyridine)-zinc(ii) pyridine solvate, C67H47N7O3Zn
  19. Crystal structure of (μ2-[2,2′-bis(diphenylphosphino)-1,1′-binaphthalene oxide-κ2O,P])-iodido copper(I), C44H32CuIOP2
  20. Crystal structure of 6,8-diphenyl-2-(4-fluorophenyl)-2,3-dihydroquinolin-4(3H)-one, C27H20FNO
  21. Crystal structure of 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetrahexoxycalix[4]arene, C68H104O4
  22. Crystal structure of N,N′–bis(pyridin-4-ylmethyl)pyrazine-2,3-dicarboxamide dihydrate, C18H20N6O4
  23. Crystal structure of a diaqua-bis(3,5-di(1H-imidazol-1-yl)pyridine-κN)-bis(2-(4-carboxy-phenyl)acetato-κO]manganese(II), C40H36MnN10O10
  24. Crystal structure of 4-(4-hydroxy-3-methoxy-phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid methyl ester, C21H25NO5
  25. Crystal structure of (E)-4,4′-(ethene-1,2-diyl)bis(3-nitrobenzoic acid) 1.5 hydrate, C16H13N2O9.5
  26. Crystal structure of (E)-2-(5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-5-((4-fluorophenyl)diazenyl)-4-methylthiazole, C23H17F2N5OS
  27. Crystal structure of the co-crystalline adduct 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide - acetic acid (1/1), C21H24N4O4S ⋅ C2H4O2
  28. Synthesis and crystal structure of 2-((5-chlorobenzo[c][1,2,5]thiadiazol-4-yl)amino)-4,5-dihydro-1H-imidazol-3-ium tetraphenylborate, C33H29BClN5S
  29. Crystal structure of (4-chlorophenyl)(3-ferrocenyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)methanone, C21H14ClF3FeN2O
  30. Crystal structure of (S)-benzyl 3-(benzylcarba-moyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, C25H24N2O3
  31. Crystal structure of 5-acetyl-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, C15H17FN2O4
  32. Crystal structure of 2-(4-fluorophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16FIN2
  33. Crystal structure of methyl 1H-indole-2-carboxylate, C10H9NO2
  34. Crystal structure of 2,3-diphenyl-1-[(dipropylamino)acetyl]-1,3-diazaspiro[4.5]decan-4-one, C28H37N3O2
  35. Crystal structure of 1-(2H-1,3-benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propan-1-one, C13H12N2O3
  36. Crystal structure of 2,9-dibromo-1,10-phenanthroline, C12H6Br2N2
  37. Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S
  38. Crystal structure of trans-bis((E)-7-oxo-4-(phenyldiazenyl)cyclohepta-1,3,5-trien-1-olato)-κ2O,O′)-bis(pyridine-κN)cobalt(II), C36H28CoN6O4
  39. Crystal structure of 2-(4-methyl-3-phenylthiazol-2(3H)-ylidene)malononitrile, C13H9N3S
  40. Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S
  41. Crystal structure of chlorido{[3-(η5-cyclopenta-dienyl)-2,2,3-trimethyl-1-phenylbutylidene] azanido-κN}[η2(N,O)-N,N-dimethylhydroxylaminato]titanium(IV), C20H27ClN2OTi
  42. Crystal Structure of 1,1′-dimethyl-[4,4′-bipyridine]-1,1′-diium tetrachloridozincate(II), C12H14Cl4N2Zn
  43. Crystal structure of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde, C11H12N2O3
  44. Crystal structure of 2,3-diphenyl-1-(morpholin-4-ylacetyl)-1,3-diazaspiro[4.5]decan-4-one, C26H31N3O3
  45. Crystal structure of 3,3-dimethyl-3,4-dihydro-1H-benzo[c]chromene-1,6(2H)-dione, C15H14O3
  46. Crystal structure of bis(2-(2-hydroxymethyl)pyridine-κ2N,O)-bis(pivalato-κO)nickel(II), C22H32N2NiO6
  47. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(1H-pyrazole-3-carboxylato-κ2N,O)manganese(II) trihydrate, C20H20N6O7Mn
  48. The crystal structure of 3-aminopropan-1-aminium iodide, C3H11N2I
  49. Crystal structure of ethyl 1-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole-4 carboxylate, C12H12ClN3O2
  50. Crystal structure of 4,4′-((1Z,1′Z)-2,2′-(2,5-diethoxy-1,4-phenylene)bis(ethene-2,1-diyl))dipyridine, C24H24N2O2
  51. Crystal structure of (16S)-12,16-epoxy-11,14-dihydroxy-17(15/16)-abeo-3a,18-cyclo-8,11,13-abietatrien-7-one, C20H24O4
  52. Crystal structure of aquadichlorido(2,4,6-tri-2-pyridyl-1,3,5-triazine-κ3N,N′,N′′)nickel(II) monohydrate, C18H16Cl2N6NiO2
  53. Crystal structure of catena-poly[dichlorido-(μ-ethane-1,2-diyl-bis-(pyridyl-4-carboxylate-κN:N′)mercury(II)], C15H14Cl2HgN2O4
  54. Crystal structure of methyl 2-acetamido-5-chlorbenzoate, C10H10ClNO3
  55. Crystal structure of tetrakis(μ2-3,3-dimethylacrylato-κ2O,O′)-bis(2-aminopyrimidine-κN) dicopper(II), C28H38Cu2N6O8
  56. Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2
  57. Crystal structure of 4-(2-ammonioethyl)morpholin-4-ium dichloride monohydrate, C6H18Cl2N2O2
  58. Crystal structure of 1-(3-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone O-benzyl oxime, C22H19BrN2O2
  59. Crystal structure of 2-(4-(dimethylamino)-2-fluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol monohydrate, C15H20FN7O2
  60. Crystal structure of 4-bromo-2-(1H-pyrazol-3-yl)phenol, C9H7BrN2O
  61. Crystal structure of 1,2,3,4,5-pentamethyl-1,3-cyclopentadiene, C10H16
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