Home Physical Sciences Synthesis and crystal structure of 1,3-bis[(3,4-dicyano)phenoxy]-4,6-dinitro-benzene, C22H8N6O6
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Synthesis and crystal structure of 1,3-bis[(3,4-dicyano)phenoxy]-4,6-dinitro-benzene, C22H8N6O6

  • Ateyatallah Aljuhani EMAIL logo , Musa A. Said , David L. Hughes and Andrew N. Cammidge
Published/Copyright: June 13, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 233 Issue 5

Abstract

C22H8N6O6, monoclinic, P21/n (no. 14), a = 15.3939(6) Å, b = 7.3053(3) Å, c = 16.8282(6) Å, β = 91.567(3)°, V = 1891.74(13) Å3, Z = 4, Rgt(F) = 0.0510, wRref(F2) = 0.0867, T = 140(2) K.

CCDC no.: 1814684

Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Plate, pale yellow
Size:0.08 × 0.03 × 0.01 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.12 mm−1
Diffractometer, scan mode:Xcalibur 3/Sapphire3, Thin
slice φ and ω-scans
θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:23318, 3333, 0.085
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2315
N(param)refined:339
Programs:CrysAlisPRO [1], SHELX [2, 3] , WinGX and ORTEP [4, 5]
Table 2:

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

AtomxyzUiso*/Ueq
C10.57921(15)0.8096(3)0.20185(14)0.0199(6)
C20.53242(14)0.7043(3)0.14712(13)0.0193(5)
C30.53716(15)0.5142(3)0.15288(13)0.0190(6)
C40.59101(15)0.4339(3)0.20993(14)0.0212(6)
C50.63902(15)0.5404(3)0.26216(13)0.0189(6)
C60.63195(14)0.7311(3)0.26008(13)0.0182(5)
O20.48760(10)0.7927(2)0.08682(9)0.0232(4)
C210.40277(15)0.8442(3)0.09919(14)0.0196(6)
C220.36351(16)0.8123(3)0.17038(15)0.0200(6)
C230.27956(15)0.8749(3)0.18027(13)0.0198(6)
C240.23554(15)0.9672(3)0.11806(14)0.0202(6)
C250.27591(17)0.9935(3)0.04637(15)0.0241(6)
C260.35984(16)0.9330(3)0.03719(15)0.0220(6)
C2310.23842(15)0.8575(3)0.25549(14)0.0227(6)
N2310.20400(14)0.8493(3)0.31519(13)0.0314(5)
C2410.15022(17)1.0347(3)0.13437(14)0.0237(6)
N2410.08405(14)1.0852(3)0.15378(13)0.0352(6)
N30.48709(13)0.3912(3)0.09940(12)0.0267(5)
O310.42934(11)0.4568(2)0.05668(10)0.0315(4)
O320.50654(12)0.2285(2)0.10111(10)0.0379(5)
N50.70039(13)0.4432(3)0.31619(12)0.0261(5)
O510.75237(12)0.5349(2)0.35598(10)0.0360(5)
O520.69727(11)0.2753(2)0.31646(10)0.0344(5)
O60.67834(10)0.8492(2)0.30921(9)0.0239(4)
C610.65818(15)0.8576(3)0.38875(13)0.0195(6)
C620.58248(15)0.7833(3)0.41665(14)0.0196(6)
C630.56391(14)0.8028(3)0.49640(13)0.0178(5)
C640.62098(15)0.8988(3)0.54776(13)0.0197(6)
C650.69742(16)0.9701(3)0.51824(15)0.0224(6)
C660.71587(16)0.9497(3)0.43899(14)0.0217(6)
C6310.48516(16)0.7239(3)0.52597(13)0.0215(6)
N6310.42304(14)0.6595(3)0.54914(12)0.0308(5)
C6410.59660(16)0.9205(3)0.62918(16)0.0250(6)
N6410.57146(15)0.9336(3)0.69278(13)0.0365(6)
H10.5752(13)0.941(3)0.2002(11)0.016(6)*
H220.3917(13)0.754(3)0.2123(12)0.022(6)*
H250.2473(14)1.055(3)0.0023(13)0.023(6)*
H260.3892(14)0.952(3)−0.0117(13)0.017(6)*
H40.5943(15)0.304(3)0.2118(13)0.035(7)*
H620.5419(14)0.719(3)0.3833(12)0.023(6)*
H650.7371(14)1.032(3)0.5518(12)0.017(6)*
H660.7688(13)0.995(2)0.4190(11)0.010(6)*
Table 3:

Short intermolecular contacts, ‘weak hydrogen bonds’, in Ångstroms and degrees.

D–H⋯Ad(D–H)d(H⋯A)d(D⋯A)<(DHA)
C(22)–H(22)⋯N(241)#10.92(2)2.59(2)3.468(3)160.1(17)
C(26)–H(26)⋯O(32)#20.96(2)2.59(2)3.362(3)137.7(15)
C(62)–H(62)⋯N(241)#10.95(2)2.24(2)3.147(3)157.9(17)
C(65)–H(65)⋯N(231)#30.94(2)2.54(2)3.416(3)154.8(17)
C(25)–H(25)⋯O(51)#40.96(2)2.55(2)3.221(3)126.8(16)

  1. Symmetry transformations used to generate equivalent atoms:#1: ½ − x, y − ½, ½ − z; #2: 1 − x, 1 − y, −z; #3: 1 − x, 2 − y, 1 − z; #4: x − ½, 1½ − y, z − ½.

Source of material

1,5-Difluoro-2,4-dinitrobenzene (0.2 g, 1 mmol), 4-hydroxyphthalonitrile (0.3 g, 2.1 mmol) and potassium carbonate (0.274 g, 2.0 mmol) were added to acetone (7 mL) and the mixture was stirred at room temperature for 24 h. The solvent was removed and the residue redissolved in DCM. This was washed with water and the washings were extracted with DCM three times. The combined organic extracts were dried over MgSO4 and the solvent removed under reduced pressure. The product was purified by column chromatography (eluting with DCM). Recrystallization from acetone gave the title compound as a yellow crystalline solid (0.3 g, 66%). Mp. 197 °C; 1H NMR (500 MHz, Acetone) δ 9.04 (s, 1H), 8.14 (d, J = 8.8 Hz, 2H), 7.96 (d, J = 2.5 Hz, 2H), 7.80 (dd, J = 8.8, 2.5 Hz, 2H), 7.73 (s, 1H); 13C NMR (126 MHz, Acetone) δ 160.10, 153.48, 139.12, 137.36, 126.49, 124.56, 124.31, 118.82, 117.81, 116.11, 115.74, 112.56; IR (KBr, cm−1): 3047, 2240, 1630, 1536.

Experimental details

The structure was determined by the intrinsic phasing routines in the SHELXT program [2] and refined by full-matrix least-squares methods, in SHELXL [3]. Hydrogen atoms were included in idealized positions, but then allowed to refine freely. The figure was drawn with ORTEP [4, 5] .

Discussion

1,2-Cyano-containing benzene compounds or phthalonitriles are important precursors for phthalocyanine molecules [6] and have potential uses in composite matrices, adhesives, sensitizers and pigments [7], [8], [9], [10], [11]. As part of our ongoing work on the synthesis and study of phthalocyanine dimers, we targeted the title novel compound as a linker unit.

The synthesis of the bis-phthalonitrile is a straightforward procedure which can be achieved by the substitution reaction method, mixing 4-hydroxyphthalonitrile with 1,5-difluoro-2,4-dinitrobenzene in acetone in the presence of freshly ground potassium carbonate. After workup, purification over silica gel gave the target compound as the second fraction. The 1H-NMR spectrum shows singlets at ca 9.05 and 7.75 p.p.m. assigned to the two protons of the bridging benzene ring. This easily prepared bis-phthalonitrile is a potential candidate for making a variety of dimers of phthalocyanines which are unique in their electronic and optical properties [12].

The crystal structure of the title compound shows an approximately planar central C6H2(NO2)2(O)2 group. The two nitro groups are rotated about the C—N bonds by 10.93(14) and 9.05(14)°. The phthalonitrile groups are turned out of the central plane by rotation about the C(2)—O(2) and C(6)—O(6) bonds (by 88.05(14) and 68.16(11)°, respectively) and aligned so that the normals to these C6 rings are approximately perpendicular (85.82(7) and 77.29(7)°, respectively) to the normal to the central ring plane. The bond lengths and angles are within normal ranges and are comparable to those observed in similar structures [13]. Molecules are connected through ‘weak hydrogen bonds’, the shortest of which is for C(62)—H(62)⋯N(2411) where the H⋯N distance is 2.24(4) Å Table 3. The dicyanophenyl rings form a short-range stack and are close to parallel (the angles between their normals are zero or 10.53(11)°), but with, in some cases, limited overlap of the rings; shorter interactions within this stack include C(24)⋯C(644) at 3.40 Å.

References

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Received: 2018-02-01
Accepted: 2018-04-12
Published Online: 2018-06-13
Published in Print: 2018-08-28

©2018 Ateyatallah Aljuhani et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 2-amino-4-(2,4-dinitrophenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo-pyran, C18H16N4O6
  3. Crystal structure of catena-poly[(μ3-5-carboxy-2-(pyridin-4-yl)benzoato-κ5O,O′:O′′,O′′′:O′′′)(1,10-phenanthroline-κ2N,N′)cadmium(II)], C100H60N12O16Cd4
  4. Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C19H18N2O6
  5. Crystal structure of 1-{4-[(2-hydroxy-5-methyl benzylidene)amino]phenyl}ethanone O-ethyl-oxime, C18H20N2O2
  6. Crystal structure of bis{4-methyl-2-((E)-((4-((E)-1-(ethoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O)}copper(II), C36H38CuN4O4
  7. Crystal structure of bis{5-methoxy-2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}nickel(II), C34H34N4NiO6
  8. Crystal structure of poly[μ8-3-carboxyphthalat-κ8-O:O1,O1,O1:O2:O3,O3:O4)silver(I)], C9H4Ag2O6
  9. Crystal structure of 2-((E)-((4-((E)-1-(hydroxyimino)ethyl)phenyl)iminio)methyl)-5-methoxyphenolate, C16H16N2O3
  10. Crystal structure of (E)-1-(4-(((E)-2-hydroxy-3-methoxybenzylidene)amino)phenyl)ethan-1-one oxime, C16H16N2O3
  11. The crystal structure of 2-(tert-butyl)-4-chloro-6-phenyl-1,3,5-triazine, C13H14Cl1N3
  12. Crystal structure of (6,6′-(((((2-aminoethyl)azanediyl)bis(ethane-2,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dichlorophenolato)-κ6N,N′,N′′,N′′′,O,O′)cadmium(II) – ethanol – water (1/1/1), C22H28CdCl4N4O4
  13. Crystal structure of 6-chloro-N-methylpyrimidin-4-amine, C5H6ClN3
  14. Synthesis and crystal structure of bis{((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)-2-naphtholato-κ2N,O}nickel(II), C40H34N4NiO4
  15. Crystal structure of (E)-2-(4-bromophenyl)ethenesulfonyl fluoride (C8H6BrFO2S)
  16. Synthesis and crystal structure of 2,2′-ethylenedioxybis(benzimide)-2,2′-bis[O-(1-propyloxyamide)]oxime-4,4′,6,6′-tetrachlorodiphenol, C36H34Cl4N4O8
  17. Crystal structure of bis(N-(1-(pyrazin-2-yl)ethylidene)nicotinohydrazonato-κ3N,N′,O)cadmium(II) – methanol (1/1), C26H28N10O4Zn
  18. Crystal structure of diaqua-(N-(1-(pyrazin-2-yl)ethylidene)nicotinohydrazonato-κ3N,N′,O)-bis(nitrato-κ2O,O′)samarium(III), C12H14N7O9Sm
  19. Crystal structure of hexaaqua-{(E)-N′-(1-(pyrazin-2-yl)ethylidene)isonicotinohydrazide-κ3N,N′,O}praseodym(III) trichloride monohydrate, C12H25Cl3N5O8Pr
  20. Crystal structure of methyl 4-(3-cyanophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C21H22N2O3
  21. Crystal structure of ethyl 2-amino-4-(2-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C22H19NO6
  22. Crystal structure of 2,12-dibromo-5,15-dihexyl-5,15-dihydrobenzo [1,2-b:5,6-c′]dicarbazole, C38H38Br2N2
  23. Crystal structure of ethyl 2-amino-4-(3-hydroxy-4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C22H19NO7
  24. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO5
  25. Crystal structure of 2-hydroxy-N′-(pyrimidin-2-yl)benzohydrazide, C11H10N4O2
  26. Crystal structure of 2-(3,4-dimethylphenyl)-1,8-naphthyridine, C16H14N2
  27. Crystal structure of ethyl 4-(3,4-dimethylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C23H29NO3
  28. Crystal structure of ethyl 4-(3-cyanophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C22H24N2O3
  29. Crystal structure of 7β,9β-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  30. Crystal structure of Ent-7β,20-epoxy-kaur-16-en-1β,6α,7α,14α,15α-pentaol-20-one, C20H30O8
  31. Crystal structure of 1,4-bis(benzo[d][1,3]dioxol-5-ylmethyl)dihydro-1H,3H-furo[3,4-c]furan-3a(4H)-yl acetate, C22H20O8
  32. Crystal structure of methyl 2-((4-((2-nitrophenoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl) benzoate, C18H16N4O5
  33. Crystal structure of diaqua-bis(5-carboxy-1-methyl-1H-imidazole-4-carboxylato-κ2N,O)zinc(II), C12H14N4O10Zn
  34. Hydrothemal synthesis and crystal structure of triaqua-bis(5-carboxy-1-methyl-1H-imidazole-4-carboxylato-κ2N,O;κ1O)manganese(II), C12H16N4O11Mn
  35. Redetermination of methyl 4-(4-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C20H22ClNO3
  36. Crystal structure of bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-methyl-imdazol)-κN}-dithiocyano-κN-zinc(II) C24H22N12S2Zn
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  38. Crystal structure of bis(η6-cymene)-tri-μ2-chlorido-ruthenium(II) tetrafluoroborate, C20H28BCl3F4Ru2
  39. Crystal structure of 3,6-diphenyl-7H-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazine, C16H12N4S
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  44. Crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate trihydrate, C35H33NO12
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  46. The crystal structure of (E)-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran-3-carbaldehyde, C18H14O3
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  48. Crystal structure of ethyl-5-formyl-3,4-dimethylpyrrole-2-carboxylate — N-(5-ethoxycarbonyl-3,4-dimethylpyrrole)-2-methylene-5-nitrobenzene-1,2-diamine (1:1), C26H31N5O7
  49. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-6-bromo-4-chlorophenol, C14H12BrClN2O
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  52. Crystal structure of 1-(5-bromo-2-(4-methoxyphenyl)-1H-indol-7-yl)ethanone oxime, C17H15BrN2O2
  53. Crystal structure of poly-{diaqua-bis[(μ2-3-nitrobenzenesulfonylglycine-κ3N:O:O′)(4,4′-bipyridine)manganese(II)]}-dimethylformamide (1/1), C39H35Mn2N9O15S2
  54. Crystal structure of 4-(dimethylamino)-1-(prop-2-yn-1-yl)pyridin-1-ium perchlorate, C10H13ClN2O4
  55. Crystal structure of 2-amino-5-oxo-4-(4-chloro-phenyl)-4,5,6,7-tetrahydro-cyclopenta[b]pyran-3-carbonitrile, C15H11ClN2O2
  56. Crystal structure of triaqua-(pyridine-2,6-dicarboxylato-κ3O,N,O′)cobalt(II) – 6-phenyl-1,3,5-triazine-2,4-diamine (1/1), C16H18CoN6O7
  57. Crystal structure of ethyl 2-amino-4-(3-cyanophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C21H22N2O4
  58. Crystal structure of 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro-3-nitrophenyl)diazene 1-oxide, C12H5Cl2N5O7
  59. Crystal structure of 3,4-dimethyl-2,6-dinitrophenol, C8H8N2O5
  60. Crystal structure of 1,2-dimethyl-3,5-dinitrobenzene, C8H8N2O4
  61. Crystal structure of ethyl 4-(3-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C21H24ClNO3
  62. Crystal structure of N-(4-chlorophenyl)-2-(2,6-dichlorophenyl)acetamide, C14H10Cl3NO
  63. Crystal structure of 2-amino-4-(4-fluorophenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2c] chromene, C19H11FN2O3
  64. The crystal structure of (4-nitrophenyl) (5-ferrocenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl) methanone, C21H12F3FeN3O3
  65. Crystal structure of 5,5′-((3-hydroxy-4-methoxyphenyl)methylene)bis(1,3-diethyl-6-hydroxy-2-thioxo-2,3-dihydropyrimidin-4(1H)-one), C24H30N4O6S2
  66. Crystal structure of (3aR,4R,5R,7R,8S,9R,9aS,12R)-7-ethyl-5-(1-hydroxy-2-((R)-3-hydroxypyrrolidin-1-yl)ethoxy)-4,7,9,12-tetramethyldecahydro-4,9a-propanocyclopenta[8]annulene-3,8-diol – a pleuromutilin derivative, C26H41NO5
  67. Crystal structure of bis(μ2-3-formyl-5-methoxy-2-oxidobenzoato-κ3O,O′:O′)-hexapyridine-dicadmium(II) – pyridine (1/1), C53H47Cd2N7O10
  68. Crystal structure of ethyl 2-amino-4-(3-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C22H19NO6
  69. Crystal structure of methyl 4-(3,5-ditrifluoromethylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate — water (2/1), C22H21F6NO3
  70. Crystal structure of 2-(4-bromophenyl)-2,3-dihydro-1H-perimidine, C17H13BrN2
  71. Crystal structure of (5-ethyl-2-(4-methoxyphenyl)-1,3-dioxan-5-yl)methanol, C14H20O4
  72. Crystal structure of (E)-N-(4-bromo-2-(1-(hydroxyimino)ethyl)phenyl)benzamide, C15H13BrN2O2
  73. Crystal structure of caffeinium triiodide – caffeine (1/1), C16H21I3N8O4
  74. Crystal structure of methyl 2-methyl-4-(3-methoxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO4
  75. Crystal structure of (E)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H28O2
  76. Crystal structure of 1,4-bis(2-azidoethyl)piperazine-1,4-diium dichloride, C8H18N8Cl2
  77. The crystal structure of dichlorido-(1,3-bis(2,6-dimethylphenyl)-1H-imidazol-2(3H)-ylidene)-(morpholine-κ1N)palladium(II), C23H29Cl2N3OPd(II)
  78. The crystal structure of 1-((5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-yl)methyl)-1,3-diphenylurea, C24H21ClN4O
  79. Crystal structure of 6-(2-bromoacetamido)tetrahydro-2H-pyran-2,3,4,5-Tetrayl tetraacetate, C16H22BrNO10
  80. Crystal structure of 5-methylpyrazine-2-carbohydrazide, C6H8N4O
  81. Crystal structure of catena-poly[(μ2-5-(tert-butyl)isophthalato-κ4O,O′:O′′,O′′′)(-4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)manganese(II)], C32H28N4O5Mn
https://doi.org/10.1515/ncrs-2018-0053
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 2-amino-4-(2,4-dinitrophenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo-pyran, C18H16N4O6
  3. Crystal structure of catena-poly[(μ3-5-carboxy-2-(pyridin-4-yl)benzoato-κ5O,O′:O′′,O′′′:O′′′)(1,10-phenanthroline-κ2N,N′)cadmium(II)], C100H60N12O16Cd4
  4. Crystal structure of 2-amino-4-(3,4,5-trimethoxy-phenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C19H18N2O6
  5. Crystal structure of 1-{4-[(2-hydroxy-5-methyl benzylidene)amino]phenyl}ethanone O-ethyl-oxime, C18H20N2O2
  6. Crystal structure of bis{4-methyl-2-((E)-((4-((E)-1-(ethoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O)}copper(II), C36H38CuN4O4
  7. Crystal structure of bis{5-methoxy-2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}nickel(II), C34H34N4NiO6
  8. Crystal structure of poly[μ8-3-carboxyphthalat-κ8-O:O1,O1,O1:O2:O3,O3:O4)silver(I)], C9H4Ag2O6
  9. Crystal structure of 2-((E)-((4-((E)-1-(hydroxyimino)ethyl)phenyl)iminio)methyl)-5-methoxyphenolate, C16H16N2O3
  10. Crystal structure of (E)-1-(4-(((E)-2-hydroxy-3-methoxybenzylidene)amino)phenyl)ethan-1-one oxime, C16H16N2O3
  11. The crystal structure of 2-(tert-butyl)-4-chloro-6-phenyl-1,3,5-triazine, C13H14Cl1N3
  12. Crystal structure of (6,6′-(((((2-aminoethyl)azanediyl)bis(ethane-2,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dichlorophenolato)-κ6N,N′,N′′,N′′′,O,O′)cadmium(II) – ethanol – water (1/1/1), C22H28CdCl4N4O4
  13. Crystal structure of 6-chloro-N-methylpyrimidin-4-amine, C5H6ClN3
  14. Synthesis and crystal structure of bis{((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)-2-naphtholato-κ2N,O}nickel(II), C40H34N4NiO4
  15. Crystal structure of (E)-2-(4-bromophenyl)ethenesulfonyl fluoride (C8H6BrFO2S)
  16. Synthesis and crystal structure of 2,2′-ethylenedioxybis(benzimide)-2,2′-bis[O-(1-propyloxyamide)]oxime-4,4′,6,6′-tetrachlorodiphenol, C36H34Cl4N4O8
  17. Crystal structure of bis(N-(1-(pyrazin-2-yl)ethylidene)nicotinohydrazonato-κ3N,N′,O)cadmium(II) – methanol (1/1), C26H28N10O4Zn
  18. Crystal structure of diaqua-(N-(1-(pyrazin-2-yl)ethylidene)nicotinohydrazonato-κ3N,N′,O)-bis(nitrato-κ2O,O′)samarium(III), C12H14N7O9Sm
  19. Crystal structure of hexaaqua-{(E)-N′-(1-(pyrazin-2-yl)ethylidene)isonicotinohydrazide-κ3N,N′,O}praseodym(III) trichloride monohydrate, C12H25Cl3N5O8Pr
  20. Crystal structure of methyl 4-(3-cyanophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C21H22N2O3
  21. Crystal structure of ethyl 2-amino-4-(2-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C22H19NO6
  22. Crystal structure of 2,12-dibromo-5,15-dihexyl-5,15-dihydrobenzo [1,2-b:5,6-c′]dicarbazole, C38H38Br2N2
  23. Crystal structure of ethyl 2-amino-4-(3-hydroxy-4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C22H19NO7
  24. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO5
  25. Crystal structure of 2-hydroxy-N′-(pyrimidin-2-yl)benzohydrazide, C11H10N4O2
  26. Crystal structure of 2-(3,4-dimethylphenyl)-1,8-naphthyridine, C16H14N2
  27. Crystal structure of ethyl 4-(3,4-dimethylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C23H29NO3
  28. Crystal structure of ethyl 4-(3-cyanophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C22H24N2O3
  29. Crystal structure of 7β,9β-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  30. Crystal structure of Ent-7β,20-epoxy-kaur-16-en-1β,6α,7α,14α,15α-pentaol-20-one, C20H30O8
  31. Crystal structure of 1,4-bis(benzo[d][1,3]dioxol-5-ylmethyl)dihydro-1H,3H-furo[3,4-c]furan-3a(4H)-yl acetate, C22H20O8
  32. Crystal structure of methyl 2-((4-((2-nitrophenoxy)methyl)-1H-1,2,3-triazol-1-yl)methyl) benzoate, C18H16N4O5
  33. Crystal structure of diaqua-bis(5-carboxy-1-methyl-1H-imidazole-4-carboxylato-κ2N,O)zinc(II), C12H14N4O10Zn
  34. Hydrothemal synthesis and crystal structure of triaqua-bis(5-carboxy-1-methyl-1H-imidazole-4-carboxylato-κ2N,O;κ1O)manganese(II), C12H16N4O11Mn
  35. Redetermination of methyl 4-(4-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C20H22ClNO3
  36. Crystal structure of bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-methyl-imdazol)-κN}-dithiocyano-κN-zinc(II) C24H22N12S2Zn
  37. Crystal structure of (5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl furan-2-carboxylate, C10H7FN2O5
  38. Crystal structure of bis(η6-cymene)-tri-μ2-chlorido-ruthenium(II) tetrafluoroborate, C20H28BCl3F4Ru2
  39. Crystal structure of 3,6-diphenyl-7H-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazine, C16H12N4S
  40. Synthesis and crystal structure of 1,3-bis[(3,4-dicyano)phenoxy]-4,6-dinitro-benzene, C22H8N6O6
  41. Crystal structure of ethyl 2-amino-4-(2,6-dichlorophenyl)-7-methyl-5-oxo-4H,5H-pyrano [4,3-b]pyran-3-carboxylate, C18H15Cl2NO5
  42. Crystal structure of poly[μ3-hydroxy-(μ5-(5-(2-carboxylatophenoxy)isophthalato-κ6O1:O2:O3:O4:O5,O6)-(μ2-1,4-di(1H-imidazol-1-yl)butane-κ2N:N′)dicobalt(II)] hemihydrate, C25H22Co2N4O8.5
  43. Crystal structure of methyl 4-(4-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C20H22BrNO3
  44. Crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-olate trihydrate, C35H33NO12
  45. Crystal structure of 2,5-bis(4-(10H-phenothiazin-10-yl)phenyl)-1,3,4-oxadiazole, C38H24N4OS2
  46. The crystal structure of (E)-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl)benzofuran-3-carbaldehyde, C18H14O3
  47. Crystal structure of bis{5H-dibenzo[c,f][1,5]oxabismocin-12(7H)-yl} carbonate, C29H24O5Bi2
  48. Crystal structure of ethyl-5-formyl-3,4-dimethylpyrrole-2-carboxylate — N-(5-ethoxycarbonyl-3,4-dimethylpyrrole)-2-methylene-5-nitrobenzene-1,2-diamine (1:1), C26H31N5O7
  49. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-6-bromo-4-chlorophenol, C14H12BrClN2O
  50. Crystal structure of (Z)-2-(4-chlorophenyl)-4-(furan-2-yl(phenylamino)methylene)-5-methyl-2,4-dihydro-3H-pyrazol-3-one, C21H16ClN3O2
  51. Crystal structure of N2,N4-dibutyl-6-chloro-N2,N4-bis(1,2,2,6,6-pentamethylpiperidin-4-yl)-1,3,5-triazine-2,4-diamine, C31H58ClN7 – Important intermediate of Chimassorb 119 synthesis
  52. Crystal structure of 1-(5-bromo-2-(4-methoxyphenyl)-1H-indol-7-yl)ethanone oxime, C17H15BrN2O2
  53. Crystal structure of poly-{diaqua-bis[(μ2-3-nitrobenzenesulfonylglycine-κ3N:O:O′)(4,4′-bipyridine)manganese(II)]}-dimethylformamide (1/1), C39H35Mn2N9O15S2
  54. Crystal structure of 4-(dimethylamino)-1-(prop-2-yn-1-yl)pyridin-1-ium perchlorate, C10H13ClN2O4
  55. Crystal structure of 2-amino-5-oxo-4-(4-chloro-phenyl)-4,5,6,7-tetrahydro-cyclopenta[b]pyran-3-carbonitrile, C15H11ClN2O2
  56. Crystal structure of triaqua-(pyridine-2,6-dicarboxylato-κ3O,N,O′)cobalt(II) – 6-phenyl-1,3,5-triazine-2,4-diamine (1/1), C16H18CoN6O7
  57. Crystal structure of ethyl 2-amino-4-(3-cyanophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C21H22N2O4
  58. Crystal structure of 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro-3-nitrophenyl)diazene 1-oxide, C12H5Cl2N5O7
  59. Crystal structure of 3,4-dimethyl-2,6-dinitrophenol, C8H8N2O5
  60. Crystal structure of 1,2-dimethyl-3,5-dinitrobenzene, C8H8N2O4
  61. Crystal structure of ethyl 4-(3-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C21H24ClNO3
  62. Crystal structure of N-(4-chlorophenyl)-2-(2,6-dichlorophenyl)acetamide, C14H10Cl3NO
  63. Crystal structure of 2-amino-4-(4-fluorophenyl)-3-cyano-5-oxo-4H,5H-pyrano[3,2c] chromene, C19H11FN2O3
  64. The crystal structure of (4-nitrophenyl) (5-ferrocenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl) methanone, C21H12F3FeN3O3
  65. Crystal structure of 5,5′-((3-hydroxy-4-methoxyphenyl)methylene)bis(1,3-diethyl-6-hydroxy-2-thioxo-2,3-dihydropyrimidin-4(1H)-one), C24H30N4O6S2
  66. Crystal structure of (3aR,4R,5R,7R,8S,9R,9aS,12R)-7-ethyl-5-(1-hydroxy-2-((R)-3-hydroxypyrrolidin-1-yl)ethoxy)-4,7,9,12-tetramethyldecahydro-4,9a-propanocyclopenta[8]annulene-3,8-diol – a pleuromutilin derivative, C26H41NO5
  67. Crystal structure of bis(μ2-3-formyl-5-methoxy-2-oxidobenzoato-κ3O,O′:O′)-hexapyridine-dicadmium(II) – pyridine (1/1), C53H47Cd2N7O10
  68. Crystal structure of ethyl 2-amino-4-(3-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C22H19NO6
  69. Crystal structure of methyl 4-(3,5-ditrifluoromethylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate — water (2/1), C22H21F6NO3
  70. Crystal structure of 2-(4-bromophenyl)-2,3-dihydro-1H-perimidine, C17H13BrN2
  71. Crystal structure of (5-ethyl-2-(4-methoxyphenyl)-1,3-dioxan-5-yl)methanol, C14H20O4
  72. Crystal structure of (E)-N-(4-bromo-2-(1-(hydroxyimino)ethyl)phenyl)benzamide, C15H13BrN2O2
  73. Crystal structure of caffeinium triiodide – caffeine (1/1), C16H21I3N8O4
  74. Crystal structure of methyl 2-methyl-4-(3-methoxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO4
  75. Crystal structure of (E)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-phenylprop-2-en-1-one, C23H28O2
  76. Crystal structure of 1,4-bis(2-azidoethyl)piperazine-1,4-diium dichloride, C8H18N8Cl2
  77. The crystal structure of dichlorido-(1,3-bis(2,6-dimethylphenyl)-1H-imidazol-2(3H)-ylidene)-(morpholine-κ1N)palladium(II), C23H29Cl2N3OPd(II)
  78. The crystal structure of 1-((5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-yl)methyl)-1,3-diphenylurea, C24H21ClN4O
  79. Crystal structure of 6-(2-bromoacetamido)tetrahydro-2H-pyran-2,3,4,5-Tetrayl tetraacetate, C16H22BrNO10
  80. Crystal structure of 5-methylpyrazine-2-carbohydrazide, C6H8N4O
  81. Crystal structure of catena-poly[(μ2-5-(tert-butyl)isophthalato-κ4O,O′:O′′,O′′′)(-4′-(pyridin-4-yl)-2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)manganese(II)], C32H28N4O5Mn
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