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Crystal structure of pyrene-4-aldehyde, C17H10O

  • Miao Bao-Xi , Zhang Li-Fang and Zhao Yun EMAIL logo
Published/Copyright: September 27, 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

C17H10O, monoclinic, P21/c (no. 14), a = 9.3121(19) Å, b = 8.0958(16) Å, c = 14.944(3) Å, β = 106.06(3)°, V = 1082.7(4) Å3, Z = 4, Rgt(F) = 0.0488, wRref(F2) = 0.1418, T = 293(2) K.

CCDC no.: 1866559

The 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:Yellow block
Size:0.18 × 0.16 × 0.12 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:Bruker APEX II, φ and ω
θmax, completeness:27.5°, 99%
N(hkl)measured, N(hkl)unique, Rint:8542, 2430, 0.025
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1957
N(param)refined:163
Programs:SHELX [1], PLATON [2]
Table 2:

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

AtomxyzUiso*/Ueq
O10.08571(11)0.73278(15)−0.11159(8)0.0413(3)
C10.21356(16)0.70645(18)−0.10688(11)0.0312(3)
H10.22920.6473−0.15670.037*
C20.35103(15)0.75278(16)−0.03459(9)0.0225(3)
C30.35280(14)0.85347(15)0.04612(9)0.0207(3)
C40.22445(15)0.92042(17)0.06338(10)0.0257(3)
H40.13130.89900.02230.031*
C50.23448(16)1.01847(17)0.14111(10)0.0287(3)
H50.14791.06190.15130.034*
C60.37110(16)1.05240(17)0.20352(10)0.0267(3)
H60.37531.11840.25510.032*
C70.50348(15)0.98879(16)0.19010(9)0.0222(3)
C80.64717(16)1.02360(17)0.25327(9)0.0265(3)
H80.65311.09160.30430.032*
C90.77384(16)0.95971(18)0.24020(9)0.0268(3)
H90.86510.98280.28290.032*
C100.76971(14)0.85646(16)0.16119(9)0.0227(3)
C110.89839(15)0.78834(18)0.14545(10)0.0274(3)
H110.99060.80740.18820.033*
C120.89127(15)0.69253(18)0.06709(10)0.0289(3)
H120.97840.64880.05790.035*
C130.75612(15)0.66206(17)0.00307(10)0.0262(3)
H130.75290.5989−0.04940.031*
C140.62341(15)0.72504(16)0.01608(9)0.0209(3)
C150.48051(15)0.69448(16)−0.04799(9)0.0232(3)
H150.47590.6322−0.10100.028*
C160.62911(14)0.82350(15)0.09584(9)0.0191(3)
C170.49502(14)0.88801(15)0.11076(8)0.0194(3)

Source of material

All chemicals were purchased from commercial sources and used as received. The title compound was prepared by two steps. The intermediate 4-cyanopyrene was prepared by the following procedures. To a 100 mL two-necked flask, 4-bromopyrene (0.327 g, 1.164 mmol), CuCN (0.215 g, 2.4 mmol), and anhydrous DMF (30 mL) were added. The mixture was heated at 160 °C for 3 days, and then cooled down to 90 °C. Subsequently, a mixture of ethylenediamine (10 mL) and water (15 mL) was added. The resulting mixture was stirred at 90 °C for 3 h and then cooled to room temperature. The product was extracted with dichloromethane three times and the organic layer was dried over magnesium sulfate, filtered, and evaporated. A quantity of 0.2 g (76% yield) of C17H9N was isolated as pale green crystals. IR (KBr): 3043 cm−1, 2220 cm−1. 1H NMR (400 MHz, CDCl3) δ 8.66 − 8.55 (m, 2H), 8.41 − 8.25 (m, 3H), 8.22 − 8.06 (m, 4H). GC/MS MS: (C17H9N) m/z 227(M+, 100), 200(16), 100(20).

The title compound was synthesized by dehydrogenation of the above intermediate4-cyanopyrene: an oven-dried 50 mL flask which was equipped with a side arm, a condenser, and adapter was flushed with nitrogen and charged with 0.150 g (0.66 mmol) of 4-cyanopyrene and 30 mL of CH2Cl2. The solution was cooled to 0 °C in an ice-water bath and 0.8 mL of 1 M solution of DIBAL-H in n-hexane was added slowly with stirring. After 15 min, additional 0.8 mL of 1 M solution of DIBAL-H in n-hexane was added slowly. The mixture was stirred for 3 h at room temperature. The mixture was poured into 50% sulfuric acid water solution and extracted with CH2Cl2 two times. The organic layer was washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography using hexane/CH2Cl2 as an eluent to afford 0.1 g pyrene-4-aldehyde in 66% yield. IR (KBr): 2724 cm−1, 1686 cm−1. 1H NMR (400 MHz, CDCl3) δ 10.55 (d, J = 0.9 Hz, 1H), 9.64 (d, J = 8.0 Hz, 1H), 8.60 (d, J = 1.2 Hz, 1H), 8.35 (d, J = 7.7 Hz, 2H), 8.29 (d, J = 7.6 Hz, 1H), 8.22−8.02 (m, 4H). GC/MS MS: (C17H10O) m/z 230(M+, 60), 202(100), 100(25). The yellow block crystals of the title compound were obtained by slow evaporation of hexane/CH2Cl2 solution (v:v = 1/1).

Experimental details

All H atoms bond were introduced using the HFIX commond in the SHELXL program [1]. All H atoms were allowed for as riding atoms with Uiso(H) = 1.2Ueq(C). The structure was checked using PLATON [2].

Comment

Since its discovery in 1837 [3], pyrene as one of the most known polyaromatic hydrocarbons (PAHs) has been paid much attention in the development of organic fluorescent materials [4], [5], [6]. In the last decades, numerous investigations have been carried out on the design and synthesis of pyrene-based materials with a broad range of potential applications such as organic light-emitting diodes (OLED), organic field effect transistor (OFET), organic lasers, chemosensors and solar cells, etc. [7], [8], [9], [10], [11], due to their pure blue fluorescence with high quantum yield, exceptionally long fluorescence lifetime, excellent thermal stability, and high charge carrier mobility. In order to obtain excellent pyrene-based functional materials, much efforts have been made to modify its molecular structure by introducing suitable electron-donating or -accepting groups at different positions of the pyrene. The formyl group is a useful substituent group for interesting pyrene-based functional materials [12]. Generally, a direct formylation on the pyrene ring occurs almost exclusively at the electron rich 1-position of pyrene [13]. Nevertheless, pyrene-2-aldehyde have been successfully designed and synthesized through the formylation and aromatization using 4,5,9,10-tetrahydropyrene as the starting material and its crystal structure has been reported by our group recently [14]. As part of our work on pyrene-based derivatives, we synthesized pyrene-4-aldehyde using a new effective strategy through reduction of 4-cyanopyrene from 4-bromopyrene.

The single X-ray diffraction analysis shows the expected structure of the title compound pyrene-4-aldehyde. The aldehyde group locates at the 4-position of the pyrene. The C—O bond length is 1.1923(18) Å, similar to that of our previously reported pyrene-2-aldehyde [14]. The C1—C2 bond length is 1.4770(19) Å, indicating the π–π conjugation effect between the pyrene and the aldehyde group. All the carbon and oxygen atoms are nearly in a strict plane with the largest deviation 0.062(2) Å. The suprmolecular structure is also comparable with that of its isomer pyrene-2-aldehyde [14]. Firsly, two molecules of the title compound form a dimeric unit by relatively strong π–π interactions with the shortest interatomic distance of 3.359(2) Å. These dimeric structures are linked into a three-dimensional structure by weak C—H⋯π and C—H⋯O interactions.

Acknowledgements

This work was supported by the Fundamental Research Funds for the Central Universities (2017BSCXA05).

References

Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

Spek, A. L.: Single-crystal structure validation with the program PLATON. J. Appl. Crystallogr. 36 (2003) 7–13.10.1107/S0021889802022112Search in Google Scholar

Laurent, A.: Pyrene from coal tar. Ann. Chim. Phys. 66 (1837) 136–137.Search in Google Scholar

Zhang, R.; Sun, H.; Zhao,Y.; Tang, X. X.; Ni, Z. H.: Dipolar 1,3,6,8-tetrasubstituted pyrene-based blue emitters containing electro-transporting benzimidazole moieties: syntheses, structures, optical properties, electrochemistry and electroluminescence. Dyes Pigments 152 (2018) 1–13.10.1016/j.dyepig.2018.01.014Search in Google Scholar

Figueira-Duarte, T. M.; Mullen, K.: Pyrene-based materials for organic electronics. Chem. Rev. 111 (2011) 7260–7314.10.1021/cr100428aSearch in Google Scholar PubMed

Zhang, R.; Zhao, Y.; Zhang, L. F.; Xu, L.; Ni, Z. H.: A series of short axially symmetrically 1,3,6,8-tetrasubstituted pyrene-based green and blue emitters with 4-tert-butylphenyl and aryamine attachments. Dyes Pigments 130 (2016) 106–115.10.1016/j.dyepig.2016.03.020Search in Google Scholar

Zhang, R.; Zhao, Y.; Zhang, L. F.; Xu, L.; Ni, Z. H.: A series of short axially symmetrically 1,3,6,8-tetrasubstituted pyrene-based green and blue emitters with 4-tert-butylphenyl and aryamine attachments. Dyes Pigments 130 (2016) 106–115.10.1016/j.dyepig.2016.03.020Search in Google Scholar

Oniwa, K.; Kikuchi, H.; Shimotani, H.; Ikeda, S.; Asao, N.; Yamamoto, Y.; Tanigaki, K.; Jin, T. N.: 2-Positional pyrene end-capped oligothiophenes for high performance organic field effect transistors. Chem. Commun. 52 (2016) 4800–4803.10.1039/C6CC00948DSearch in Google Scholar PubMed

Yi, J. P.; Zhao, L.; Xu, W. D.; Liu, C. F.; Lai, W. Y.; Huang, W.: Pyrene-capped starburst emitters as gain media for organic lasers: design, synthesis, and stabilized lasing properties. J. Mater. Chem. C 4 (2016) 7546–7553.10.1039/C6TC01606ESearch in Google Scholar

Chu, K. H.; Zhou, Y.; Fang, Y.; Wang, L. H.; Li, J. Y.; Yao, C.: Rhodamine-pyrene conjugated chemosensors for ratiometric detection of Hg2+ ions: different sensing behavior between a spirolactone and a spirothiolactone. Dyes Pigments 98 (2013) 339–346.10.1016/j.dyepig.2013.02.019Search in Google Scholar

Liu, X.; Luo, G. P.; Cai, X. Y.; Wu, H. B.; Su, S. J.; Cao, Y.: Pyrene terminal functionalized perylene diimide as non-fullerene acceptors for bulk heterojunction solar cells. RSC Adv. 5 (2015) 83155–83163.10.1039/C5RA13188JSearch in Google Scholar

Liu, Y. F.; Jun, E. J.; Kim, G.; Lee, A. R.; Lee, J. H.; Yoon, J.: A bispyrene derivative as a selective fluorescent probe for RNA. Chem. Commun. 50 (2014) 2505–2507.10.1039/C3CC49430FSearch in Google Scholar

Yamato, T.; Fujimoto, M.; Nagano, Y.: Electrophilic substitution of 7-tert-butyl-1-substituted pyrenes. A new route for the preparation of 1,3-disubstituted pyrenes. Org. Prep. Proceed. Int. 29 (1997) 320–330.10.1080/00304949709355205Search in Google Scholar

Miao, B. X.; Tang, X. X.; Zhang, L. F.: Crystal structure of pyrene-2-carbaldehyde, C17H10O. Z. Kristallogr. NCS 233 (2018) 655–657.10.1515/ncrs-2017-0423Search in Google Scholar

Received: 2018-07-20
Accepted: 2018-09-08
Published Online: 2018-09-27
Published in Print: 2018-12-19

©2018 Miao Bao-Xi 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 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
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  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
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  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
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  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
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https://doi.org/10.1515/ncrs-2018-0254
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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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