Home Physical Sciences Crystal structure of (2Z,2′Z)-1,1′-(pyridine-2,6-diyl) bis(3-hydroxy-3-phenylprop-2-en-1-one), C23H17NO4
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Crystal structure of (2Z,2′Z)-1,1′-(pyridine-2,6-diyl) bis(3-hydroxy-3-phenylprop-2-en-1-one), C23H17NO4

  • Ai-Zhen Weng , Hai-Yuan Quan , Liu-Yang Wang , Dong-Mei She and Xiang-Dong Mei EMAIL logo
Published/Copyright: September 11, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 1

Abstract

C23H17NO4, orthorhombic, P212121 (no. 29), a = 26.3525(8) Å, b = 3.88640(10) Å, c = 34.8871(10) Å, V = 3573.01(18) Å3, Z = 8, Rgt(F) = 0.0419, wRref(F2) = 0.1086, T = 180 K.

CCDC no.: 1862148

One of the two crystallographic independent molecules of the title crystal structure is shown in the figure. 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:Rod-like, colorless
Size:0.5 × 0.15 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.10 mm−1
Diffractometer, scan mode:XtaLAB AFC12 (RINC), φ and ω-scans
θmax, completeness:27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:38528, 8079, 0.042
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 6852
N(param)refined:509
Programs:CrysAlisPRO [1], OLEX2 [2], SUPERFLIP [3], SHELX [4]
Table 2:

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

AtomxyzUiso*/Ueq
O10.38358(7)−0.0101(5)0.70532(6)0.0419(5)
H10.36150.03990.68980.063*
O20.34375(7)0.2838(5)0.64955(6)0.0424(5)
O30.50446(8)1.0387(5)0.51324(5)0.0446(5)
O40.59647(8)1.0661(6)0.52861(6)0.0440(5)
H4A0.57011.08050.51620.066*
N10.43982(8)0.6215(5)0.58924(6)0.0270(4)
C10.47164(10)−0.0544(6)0.71379(7)0.0286(5)
C20.52078(10)−0.0441(7)0.69951(8)0.0354(6)
H20.52680.04360.67510.043*
C30.56103(12)−0.1640(8)0.72141(9)0.0465(8)
H30.5938−0.15820.71160.056*
C40.55239(13)−0.2922(8)0.75783(9)0.0495(8)
H40.5794−0.37060.77260.059*
C50.50392(13)−0.3036(8)0.77216(9)0.0471(8)
H50.4982−0.38880.79670.057*
C60.46361(12)−0.1894(7)0.75040(8)0.0381(6)
H60.4308−0.20230.76020.046*
C70.42796(10)0.0657(6)0.69116(7)0.0281(5)
C80.43203(9)0.2472(6)0.65728(7)0.0276(5)
H80.46390.30080.64750.033*
C90.38808(10)0.3515(6)0.63744(7)0.0298(6)
C100.39283(10)0.5412(6)0.60045(7)0.0283(5)
C110.34961(10)0.6262(7)0.57939(8)0.0328(6)
H110.31740.57050.58830.039*
C120.35600(11)0.7947(7)0.54506(8)0.0370(6)
H120.32800.84990.53010.044*
C130.40411(11)0.8811(7)0.53300(8)0.0344(6)
H130.40910.99680.51000.041*
C140.44522(10)0.7913(6)0.55609(7)0.0287(5)
C150.49784(11)0.8883(6)0.54561(7)0.0311(6)
C160.53809(10)0.8198(7)0.57047(7)0.0310(6)
H160.53190.70950.59370.037*
C170.58735(10)0.9146(6)0.56093(8)0.0314(6)
C180.63208(10)0.8511(6)0.58547(8)0.0316(6)
C190.68008(11)0.9413(7)0.57266(9)0.0396(7)
H190.68381.04080.54860.047*
C200.72221(11)0.8858(8)0.59499(10)0.0473(8)
H200.75410.94710.58590.057*
C210.71740(11)0.7392(8)0.63089(10)0.0468(8)
H210.74590.70190.64600.056*
C220.66985(11)0.6488(8)0.64403(9)0.0448(7)
H220.66640.55070.66820.054*
C230.62768(11)0.7021(7)0.62185(8)0.0361(6)
H230.59590.63870.63100.043*
O50.84718(8)1.6599(5)0.46834(6)0.0400(5)
H5A0.82081.69800.48010.060*
O60.75474(8)1.6774(5)0.48313(5)0.0416(5)
O70.58874(7)0.9502(5)0.34839(6)0.0407(5)
O80.62747(7)0.6359(6)0.29285(6)0.0419(5)
H8A0.60550.72410.30630.063*
N20.68724(8)1.2569(5)0.40877(6)0.0272(4)
C240.88082(10)1.3758(6)0.41426(8)0.0301(5)
C250.87468(11)1.2490(8)0.37746(9)0.0388(6)
H250.84241.23500.36690.047*
C260.91638(12)1.1429(8)0.35629(9)0.0456(7)
H260.91211.06420.33130.055*
C270.96425(11)1.1541(7)0.37237(10)0.0459(8)
H270.99221.07960.35840.055*
C280.97040(12)1.2745(8)0.40874(11)0.0483(8)
H281.00271.28010.41950.058*
C290.92946(10)1.3885(7)0.42996(9)0.0385(7)
H290.93431.47330.45460.046*
C300.83712(10)1.4894(6)0.43762(7)0.0297(6)
C310.78690(10)1.4121(6)0.42775(7)0.0292(5)
H310.78011.29390.40510.035*
C320.74708(10)1.5112(6)0.45156(7)0.0295(5)
C330.69371(10)1.4298(6)0.44138(7)0.0281(5)
C340.65336(11)1.5372(7)0.46450(7)0.0321(6)
H340.65921.65100.48750.038*
C350.60465(10)1.4695(7)0.45219(8)0.0340(6)
H350.57701.53950.46680.041*
C360.59734(10)1.2989(6)0.41838(8)0.0325(6)
H360.56471.25480.40950.039*
C370.63958(9)1.1919(6)0.39739(7)0.0275(5)
C380.63386(10)1.0003(6)0.36062(7)0.0290(6)
C390.67671(10)0.8793(6)0.34132(7)0.0279(5)
H390.70880.92270.35130.033*
C400.67211(10)0.6964(6)0.30763(7)0.0291(5)
C410.71530(10)0.5554(6)0.28587(7)0.0302(6)
C420.70754(12)0.4356(7)0.24875(8)0.0389(7)
H420.67540.44660.23780.047*
C430.74763(14)0.3000(8)0.22804(10)0.0501(8)
H430.74230.22280.20310.060*
C440.79499(14)0.2788(8)0.24396(9)0.0500(8)
H440.82170.18540.23000.060*
C450.80311(12)0.3958(8)0.28077(9)0.0463(7)
H450.83530.38100.29160.056*
C460.76365(11)0.5350(7)0.30168(9)0.0378(6)
H460.76940.61540.32640.045*

Source of materials

The title compound was prepared according to the literature method [10], [11], [12]. Dimethyl pyridine-2,6-dicarboxylate (10 mmol), 60% sodium hydride (40 mmol) and xylene (50 mL) were stirred in a round-bottomed flask, and the mixing solution of acetophenone and xylene (40 mmol) was added dropwise at 383 K. The reaction mixture was heated to 433 K and refluxed 3 h. Then filered and washed 3 times by petroleum ether. The filter cake was dissolved in the mixture of glacial acetic acid (25 mL) and anhydrous ethanol (25 mL), Cooling crystallization, filtering, filter cake was washed two times by a small amount of ethanol and ethyl ether without water. The product was a brown yellow solid, which was recrystallized with glycol dimethyl ether after drying. The title compound was dissolved in acetone and cyclohexane with the optimal ratio 2 : 3 at room temperature. Colourless block crystals were obtained through slow evaporation after one weeks.

Experimental details

All H atoms were placed at calculated positions. Data reduction and empirical absorption correction were performed using Olex2 [2], the crystal structure was solved by SUPERFLIP program [3] and refined by full-matrix least-squares refinement with SHELX program [4].

Comment

Pyridine derivatives are known as important intermediates widely used in the synthesis of drugs [5, 6] and pesticides [7, 8] . Pyridine pesticides have the characteristics of high activity, low toxicity and high efficiency, and have good environmental compatibility with human beings and organisms, which opens up a new world for the development of chemical pesticides. Pyridine and benzene are bioisoster, which are similar in many aspects, but the significant difference between them is the hydrophobic parameters (benzene is 1.96, pyridine is 0.65). Therefore, the new compounds which are obtained by pyridine instead of benzene tend to show a higher biological activity, low toxicity, high systemic or higher selectivity, etc.

(2Z,2′Z)-1,1′-(pyridine-2,6-diyl)-bis(3-hydroxy-3-phenylprop-2-en-1-one) and its derivatives are important pharmaceutical and pesticides intermediates [9], [10], [11], [12]. For example, a new type of pyridine amide fungicides, has a unique mechanism, which was developed by Bayer company. It is mainly used for the prevention and control of oomycete diseases such as downy mildew, disease, etc., and interact with other compounds without resistance. The field test results show that foliar spray not only has a good control effect, it also has long-term effect [13].

The title molecule contains one pyridine ring and two symmetrical phenyl-ketone type moieties. In most cases, the enol structure of such compounds are unstable and transform into lower energy, more stable isomers, ketones or aldehydes. However, the addition of benzene ring to pyridine-based structures has found that benzene ring is conducive to stabilizing enol structures, while pyridine does not have this function. Bond lengths and angles in the title structure are in accord with a related one [14].

Acknowledgements

This work was supported by the National Key Research Development Program of China (No. 2016YFD200201 and 2016YFD0200502, 2017YFD0800705), the NSFC (No. 31772175 and 31621064), the National Basic Research Program of China (No. 2014CB932200).

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Received: 2018-06-28
Accepted: 2018-08-15
Published Online: 2018-09-11
Published in Print: 2018-12-19

©2018 Ai-Zhen Weng et al., published by De Gruyter, Berlin/Boston

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

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  50. Crystal structure of diaqua-bis(3,3-dimethylacrylato-κ2O,O′)zinc(II), C10H18ZnO6
  51. Crystal structure of dichloro-tetrakis[(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol-κN]cadmium (II), C60H74CdCl6N12O4
  52. Crystal structure of (20R)-20,25-epoxy-dammaran-3,12-dione, C30H48O3
  53. Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-((pyridin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C32H31N5O2
  54. The crystal structure of 2-(4-fluorophenyl)-1,3,4-oxadiazole, C8H5FN2O
  55. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(tri(p-tolyl)phosphine-κP)copper(I) tetrafluoroborate – 4,4′-bipyridine (2/1), C57H54BCuF4N3P2
  56. The crystal structure of 2,6-dimethyl-3,5-dinitrocyclohexa-2,5-diene-1,4-dione, C8H6N2O6
  57. The crystal structure of 2,3-dimethyl-1,4-dinitrobenzene – a Z′ = 4 structure, C8H8N2O4
  58. Crystal structure of [(1,2-η)-1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl] (1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-κ6N2,O4) rubidium (I), [Rb(diaza-18-crown-6)]Cp*, C22H41N2O4Rb
  59. Crystal structure of 2-(4-fluorophenyl)-N-phenyl-2-(phenylamino)ethanesulfonamide – toluene (1/0.5), C23.5H23FN2O2S
  60. Crystal structure of pyrene-4-aldehyde, C17H10O
  61. Crystal structure of 2-(furan-2-yl)-5-methyl-1,3-dioxane-5-carboxylic acid, C10H12O5
  62. Crystal structure of 2-(4-chlorophenyl)-3-phenyl-1,8-naphthyridine, C20H13N2Cl
  63. Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS
  64. Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2
  65. Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
  66. Crystal structure of 4-(acetoxymethyl)-6-(3-acetyl-3-(4-fluorophenyl)thioureido)cyclohex-4-ene-1,2,3-triyl triacetate, C24H26FN2O9S
https://doi.org/10.1515/ncrs-2018-0200
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of bis(6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2,4-diiodophenolato)-κ4N,N′,O,O′)cer(IV), C32H20CeI8N4O4
  3. Crystal structure of (6,6′-((ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato-κ2N,O))copper(II), C16H12Cl2CuN2O2
  4. Crystal structure of poly[aqua-(μ3-4-(pyridin-4-yl)isophthalato-κ4O,O′:O′′:O′′′)-(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:O′)samarium(III)], C26H18N2O9Sm
  5. Crystal structure of 1-{4-[(2-hydroxy-5-nitrobenzylidene)amino]phenyl}ethanone O-methyl oxime, C16H15N3O4
  6. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)-bis(μ2-1-(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)trizinc(II), C44H38Zn3N4O12
  7. Synthesis and crystal structure of bis(μ2-acetato-κ2O:O′)–bis(μ2–(8-(2-oxidophenyl)-3,6-dioxa-2,7-diazaocta-1,7-dien-1-yl)naphthalen-2-olato-κ6O:O,N,N′,O′:O′)tricobalt(II), C44H38Co3N4O12
  8. Crystal structure of poly[aqua(μ4-2,2′,2′′-nitrilotriacetato-κ6O1,O3,O5:O2:O4:O6)-yttrium(III)], C6H8NO7Y
  9. Crystal structure of catena-poly[bromido-(μ2-pyrazine-2-carboxylato-κ3N:N′,O)copper(II)], C10H6N4Cu2O4Br
  10. Crystal structure of poly[dodekais(μ2-2,6-difluorobenzoato-κ2O:O′)-bis((μ3-hexamethylenetetramine-κ3N:N′:N′′)hexacopper(II)], C48H30N4O12F12Cu3
  11. Crystal structure of methyl 4-(4-hydroxy-3-nitrophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H18N2O6
  12. Crystal structure of N-phenyl-2-(propan-2-ylidene)hydrazine-1-carbothioamide, C10H13N3S
  13. Crystal structure of sodium caesium zinc phosphate, NaCsZnP2O7
  14. Crystal structure of methyl 4-(4-isopropylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C23H29NO3
  15. Crystal structure of catena-poly[bis(μ2-1,3-di(4H-1,2,4-triazol-4-yl)benzene-κ2N:N′)-bis(thiocyanato-κ1N)cobalt(II), C22H16CoN14S2
  16. Crystal structure of catena-poly[(μ2-2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ2N:N′)-bis(2,5-di(pyridin-3-yl)-1,3,4-thiadiazole-κ1N)-bis(thiocyanato-κ1N)cobalt(II)], C38H24CoN14S5
  17. Crystal structure of bis(2,5-di(pyridin-2-yl)-1,3,4-thiadiazole-κ2N,N′)-bis(thiocyanato-κ1N)cobalt(II), C26H16CoN10S4
  18. Crystal structure of (bis((1H-benzo[d]imidazol2-yl)methyl)amine-κ3N,N′,N′′)-(pyridine-2,6-dicarboxylato-κ3N,O,O′)zinc(II) — methanol — water (1/2/1), C25H28N6O7Zn
  19. Crystal structure of catena-poly[triaqua-(μ2-5-methoxy-isophthalato-κ2O:O′)copper(II)], C9H12CuO8
  20. Structure and photochromism of 1-[2-methyl-5-phenyl-3-thienyl]-2-[2-methyl-5-(4-chlorophenyl)-3-thienyl]3,3,4,4,5,5-hexafluorocyclopent-1-ene, C27H16ClF6S2
  21. Crystal structure of methyl 4-(3-phenoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C26H27NO4
  22. Crystal structure of poly[diaqua-di-μ2-hydroxido-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ4O:O′:O′′:O′′′)-(μ4-3,4,5,6-tetrafluoro-1,2-phthalato-κ5O,O:O′:O′′:O′′′)disamarium(III)] – bipyridine (2/1), C21H11NF16O12Sm2
  23. Crystal structural of diethyl 4-(3,5-dibromo-4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, C19H21Br2NO5
  24. Crystal structure of catena-poly[tetraaqua(μ2-4-(1H-imidazol-1-yl)pyridine-κ2N:N′))zinc(II)] thiophene-2,5-dicarboxylate, C14H17N3O8ZnS
  25. Crystal structure of (20S)-20-(dimethylamino)-3-(tigloylamino)-5α-pregn-2,16-dien-4-one, C28H42N2O2
  26. Crystal structure of rac-trans-N,N′-bis(3,5-diiodosalicylidene)-1,2-cyclohexanediamine, C20H18I4N2O2
  27. Crystal structure of 2-bromo-7-(4-(dimethylamino)phenyl)-10-methylacridin-9 (10H)-one, C22H19BrN2O
  28. Crystal structure of catena-poly[(μ2-pentane-1,5-dicarboxylato-κ2O:O′)-(μ2-2-[(1H-imidazol-1-yl)methyl]-6-methyl-1H-benzimidazole-κ2N:N′)zinc(II)] sesquihydrate, C17H21N4O5.5Zn
  29. Crystal structure of ethyl 2-amino-4-(3,4-difluorophenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C21H15F2NO5
  30. Crystal structure of 9-(5-methylthiophen-2-yl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione, C18H18O3S
  31. Crystal structure of [5,5′-((propane-1,3-diylbis(azanylylidene))bis(ethan-1-yl-2-ylidene))bis(3-(ethoxycarbonyl)-2,4-dimethylpyrrol-1-ido)-κ4N,N′,N′′,N′′′]nickel(II), C23H30N4O4Ni
  32. Crystal structure of (Z)-2-(2-(1,3-dioxo-1-(phenylamino)butan-2-ylidene)hydrazineyl) terephthalic acid-dimethylsulfoxide (1/1), C18H15N3O6 ⋅ C2H6OS
  33. Crystal structure of (2E,4Z)-dimethyl 4-((phenylamino)methylene)pent-2-enedioate, C14H15N1O4
  34. Crystal structure of (2Z,2′Z)-1,1′-(pyridine-2,6-diyl) bis(3-hydroxy-3-phenylprop-2-en-1-one), C23H17NO4
  35. Crystal structure of ethyl 2-amino-4-(3-bromophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carboxylate, C21H16BrNO5
  36. Crystal structure of bis(μ2-3,5-dichloro-2-oxidobenzoato-κ4O,O′:O′,O′′)-hexakis(μ2-pivalato-κ2O:O′)-bis(pivalato-κ2O,O′)-tetrakis(1,10-phenanthroline-κ2N,N′)tetragadolinium(III), C102H108Cl4Gd4N8O22
  37. Crystal structure of catena-poly[aqua-bis(formato-κ1O)-(μ2-1,1′-(oxybis(1,4-phenylene))-bis(1H-1,2,4-triazole)-κ2N:N′)copper(II)]hydrate, C18H16CuN6O6
  38. Crystal structure of 5-bromo-2-(naphthalen-6-yl)pyridine, C15H10BrN
  39. Crystal structure of N-(4-methoxybenzyl)pyridazin-3-amine- a rare Z′ = 4 structure, C12H13N3O
  40. Crystal structure of bis(perchlorato-κ1O)-bis(3,4,5-trimethoxy-N-(pyridin-2-yl)benzamide-κ2N,O)copper(II), C32H30Cl2CuN4O16
  41. Crystal structure of methyl 4-methyl-2,5-di(pyridin-4-yl)-1H-pyrrole-3-carboxylate monohydrate C17H15N3O2⋅H2O
  42. Crystal structure of dimethyl 5-(10-(methoxycarbonyl)anthracen-9-yl) isophthalate,C26H20O6
  43. Crystal structure of tert-butyl (R)-(1-(benzylamino)-3-methoxy-1-oxopropan-2-yl)carbamate, C16H24N2O4
  44. Crystal structure of aqua-bis(1,5-dimethyl-2-phenyl-4-(((E)-4-pyridylmethylene)amino)pyrazolidin-3-one-κN)-(nitrato-κO)-(nitrato-κ2O,O′)zinc(II), C34H34N10O9Zn
  45. Crystal structure of catena-poly[dichlorido-(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)cobalt(II)] – methanol (1/1), C18H20Cl2CoN4O2
  46. Crystal structure of poly[diaqua-bis(μ2-1-(4-(1H-imidazol-1-yl)benzyl)-1H-1,2,4-triazole-κ2N:N′)manganese(II)]bis(2-carboxybenzoate) dihydrate, MnC40H40N10O12
  47. The crystal structure of 4-((3,4-dichlorobenzylidene)amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one, C18H15Cl2N3O
  48. Crystal structure of bis(2-methoxy-6-((2-(pyrimidin-2-yl)hydrazono)methyl)phenolato-κ3N,N′,O)iron(III) perchlorate, C24H22N8O8ClFe
  49. The crystal structure of 2-[4-hydroxy-3-methoxyphenyl]-4,4,5,5-tetramethylimidazoline-3-oxide-1-oxyl, C14H19N2O4
  50. Crystal structure of diaqua-bis(3,3-dimethylacrylato-κ2O,O′)zinc(II), C10H18ZnO6
  51. Crystal structure of dichloro-tetrakis[(E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol-κN]cadmium (II), C60H74CdCl6N12O4
  52. Crystal structure of (20R)-20,25-epoxy-dammaran-3,12-dione, C30H48O3
  53. Crystal structure of (E)-3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-((pyridin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C32H31N5O2
  54. The crystal structure of 2-(4-fluorophenyl)-1,3,4-oxadiazole, C8H5FN2O
  55. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(tri(p-tolyl)phosphine-κP)copper(I) tetrafluoroborate – 4,4′-bipyridine (2/1), C57H54BCuF4N3P2
  56. The crystal structure of 2,6-dimethyl-3,5-dinitrocyclohexa-2,5-diene-1,4-dione, C8H6N2O6
  57. The crystal structure of 2,3-dimethyl-1,4-dinitrobenzene – a Z′ = 4 structure, C8H8N2O4
  58. Crystal structure of [(1,2-η)-1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl] (1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-κ6N2,O4) rubidium (I), [Rb(diaza-18-crown-6)]Cp*, C22H41N2O4Rb
  59. Crystal structure of 2-(4-fluorophenyl)-N-phenyl-2-(phenylamino)ethanesulfonamide – toluene (1/0.5), C23.5H23FN2O2S
  60. Crystal structure of pyrene-4-aldehyde, C17H10O
  61. Crystal structure of 2-(furan-2-yl)-5-methyl-1,3-dioxane-5-carboxylic acid, C10H12O5
  62. Crystal structure of 2-(4-chlorophenyl)-3-phenyl-1,8-naphthyridine, C20H13N2Cl
  63. Crystal structure and photochromism of 1-(2-ethyl-5-formylthiophen-3yl)-2-(2-cyano-1,5-dimethyl-4-pyrrl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C19H14F6N2OS
  64. Crystal structure of 2-(4-bromophenyl)-1,3-dimethyl-1H-perimidin-3-ium iodide, C19H16BrIN2
  65. Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
  66. Crystal structure of 4-(acetoxymethyl)-6-(3-acetyl-3-(4-fluorophenyl)thioureido)cyclohex-4-ene-1,2,3-triyl triacetate, C24H26FN2O9S
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