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Crystal structure of pyrene-2-carbaldehyde, C17H10O

  • Miao Bao-Xi , Tang Xin-Xue and Zhang Li-Fang EMAIL logo
Published/Copyright: April 18, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 233 Issue 4

Abstract

C17H10O, monoclinic, P21/c (no. 14), a = 8.1312(16) Å, b = 7.8252(16) Å, c = 17.231(3) Å, β = 92.47(3)°, V = 1095.3(4) Å3, Z = 4, Rgt(F) = 0.0517, wRref(F2) = 0.1281, T = 293(2) K.

CCDC no.: 1834752

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:0.15 × 0.14 × 0.12 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.09 mm−1
Diffractometer, scan mode:Bruker APEX-II, ω-scans
θmax, completeness:26°, >98%
N(hkl)measured, N(hkl)unique, Rint:7793, 2121, 0.056
Criterion for Iobs, N(hkl)gt:Iobs >2 σ (Iobs), 1133
N(param)refined:162
Programs:Bruker programs [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
O10.9439(2)0.2050(2)−0.10678(9)0.0507(5)
C10.5362(3)0.2907(2)−0.04617(12)0.0326(6)
H10.50260.3529−0.09000.039*
C20.6942(3)0.2235(2)−0.04090(12)0.0292(5)
C30.7474(3)0.1309(2)0.02406(12)0.0315(6)
H30.85370.08690.02690.038*
C40.6443(3)0.1027(2)0.08490(11)0.0268(5)
C50.6931(3)0.0038(2)0.15243(12)0.0288(5)
H50.7988−0.04180.15660.035*
C60.5892(3)−0.0239(3)0.20932(12)0.0326(6)
H60.6252−0.08800.25220.039*
C70.4241(3)0.0420(2)0.20639(11)0.0300(5)
C80.3144(3)0.0129(3)0.26496(13)0.0384(6)
H80.3470−0.05370.30760.046*
C90.1562(3)0.0824(3)0.26035(14)0.0438(6)
H90.08480.06380.30020.053*
C100.1054(3)0.1797(3)0.19605(13)0.0406(6)
H10−0.00020.22570.19360.049*
C110.2095(3)0.2094(2)0.13542(13)0.0325(6)
C120.1593(3)0.3056(3)0.06735(14)0.0388(6)
H120.05330.35030.06310.047*
C130.2631(3)0.3320(3)0.00954(13)0.0345(6)
H130.22680.3947−0.03380.041*
C140.4269(3)0.2667(2)0.01291(12)0.0286(5)
C150.4810(3)0.1715(2)0.07997(12)0.0257(5)
C160.3715(3)0.1419(2)0.14055(11)0.0263(5)
C170.8042(3)0.2533(3)−0.10544(14)0.0403(6)
H170.76200.3140−0.14820.048*

Source of material

All chemicals were purchased from commercial sources and used as received without further purification. The title complex was prepared by two steps. The intermediate 2-formyl-4,5,9,10-tetrahydropyrene was prepared by the following procedure: To a stirred solution of 4,5,9,10-tetrahydropyrene (2.060 g, 10 mmol) and dichloromethyl methyl ether (1.495 g, 13 mmol) in CH2Cl2 (80 mL) was added at 0 °C a solution of titanium tetrachloride (10.95 mL, 100 mmol) in CH2Cl2 (20 mL). The mixture was stirred for 3 h at room temperature. The mixture was poured into ice-water 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 2.0358 g 2-formyl-4,5,9,10-tetrahydropyrene in 87% yield. 1H NMR (400 MHz, CDCl3) δ 9.98 (s, 1H), 7.62 (s, 2H), 7.23 (d, J = 6.8 Hz, 1H), 7.14 (d, J = 7.6 Hz, 2H), 2.97 (dd, J = 9.4, 3.6 Hz, 8H). GC/MS MS: (C17H14O) m/z 234(M+, 78), 216(18), 205(100), 189(38), 101(20).

The title compound was synthesized by dehydrogenation of the intermediate 2-formyl-4,5,9,10-tetrahydropyrene a solution of 2-formyl-4,5,9,10-tetrahydropyrene (1.170 g, 5 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (2.951 g, 13 mmol) in 100 mL of freshly-dried benzene was refluxed for two days. After removing the solvent by rotary evaporation, the residue was purified by silica gel chromatography using hexane/CH2Cl2 as an eluent to afford 1.081 g 2-pyrenyl aldehyde in 94% yield. 1H NMR (400 MHz, CDCl3) δ 10.47 (s, 1H), 8.68 (s, 2H), 8.27 (d, J = 7.6 Hz, 2H), 8.23–8.16 (m, 4H), 8.15–8.11 (m, 1H). GC—MS MS: (C17H10O) m/z 230(M+, 100), 201(95), 100(35). The yellow block crystals of the title compound were obtained by slow evaporation of hexane/CH2Cl2 solution (v:v = 1/1) and the selected crystal was structurally characterized by X-ray diffraction analysis.

Experimental details

All H atoms bond to C atoms were introduced using the HFIX commond in the SHELXL program [2], with the value of 0.93 Å or 0.96 Å for C—H bonds distances. All H atoms were allowed for as riding atoms with Uiso(H) = 1.2Ueq(C) for hydrogen atoms. The structure was checked using PLATON [3].

Discussion

In the last several decades, the research on organic fluorescent materials has gained important momentum due to their wide range of applications in organic light-emitting diodes (OLED), organic field effect transistor (OFET), organic lasers, fluorescent sensors and solar cells, etc. [4], [5], [6], [7], [8]. As a well known fluorophore, pyrene and its derivatives have been paid much attentions due to their pure blue fluorescence with high quantum yield, exceptionally long fluorescence lifetime, excellent thermal stability, and high charge carrier mobility [9], [10], [11]. Generally, the derivatization of pyrene is the key step for interesting pyrene-based functional materials. However, the active position of direct electrophilic mono substitution reaction on pyrene is almost exclusively at the electron-rich 1-position of pyrene [12], [13], [14], [15]. Compared to the derivatives with the substitutents at the 1-position of pyrene, the compounds with the substituents at 2-position are relatively limited, and only a few 2-substituted pyrenes (2-bromopyrene, 2-amionpyrrene, 2-acetylpyrene, and so on) have been obtained up to date [16], [17], [18], [19]. Recently, we synthesized one important pyrene-based derivative 2-pyrenyl aldehyde through the formylation and aromatization using 4,5,9,10-tetrahydropyrene as the starting material.

The single X-ray diffraction analysis agrees well with expected structure of the title compound. The functional group of aldehyde locates at the 2-position of pyrene. The C–O bond length is 1.198(3) Å, which is the typical double bond distance of aldehyde group. The C2–C17 bond length is 1.476(3) Å, indicating the π–π conjugation effect between the pyrene π-ring system and the aldehyde functional group. All carbon and oxygen atoms are nearly in a strict plane with the largest deviation to be 0.031(3) Å from the mean plane based on all the atoms. There is relatively strong intermolecular π–π interaction between adjacent molecules with the shortest interatomic distance is 3.366(3) Å, forming dimeric supramolecular structures. In addition, there exist weak intermolecular C–H⋯π and C–H⋯O interactions, which link the units of the title compounds into three-dimensional structure.

Acknowledgements

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

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Received: 2017-01-15
Accepted: 2018-04-04
Published Online: 2018-04-18
Published in Print: 2018-07-26

©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.

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  3. Crystal structure of 1,3,5,7-tetraazaadamantane-1,3-diium 2,5-dicarboxyterephthalate, C16H18N4O8
  4. Crystal structure of guanidinium tetrabutyl-ammonium 5-hydroxyisophthalate dihydrate, C25H50N4O7
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  60. Crystal structure of ethyl 5-formyl-3,4-dimethylpyrrole-2-carboxylate–1-(propan-2-ylidene)thiosemicarbazide (1/1), C14H22N4O3S
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  67. Crystal structure of methyl (R)-4-(o-chlorobenzoyl)-1-thia-4-azaspiro[4.5]decane-3-carboxylate, C17H20ClNO3S
  68. Crystal structure of 2-[[4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl]phenyl] methyl]-1H-isoindole-1,3(2H)-dione, C28H29N3O3
  69. The crystal structure of benzenaminium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate hydrate, C21H19NO8S
  70. Crystal structure of semiconducting potassium poly[(μ2-tetraselenido-κ2Se1:Se4)(μ2-pentaselenido-κ1Se1:Se1)argentate(I)], K3AgSe9
  71. Crystal structure of 2-isopropyl-8-methyl-phenanthrene-3,4-dione, C18H16O2
  72. Crystal structure of 2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione, C19H22O2
  73. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-4-bromophenol, C14H13BrN2O
  74. Crystal structure of 1,1-di(4-cyanophenyl)-2,2-diphenylethene, C28H18N2
  75. Crystal structure of bis(hydroxylamido-κ2O,N)-oxido(1H-pyrazole-3-carboxylato-κ2O,N)vanadium(V), C4H7N4O5V
  76. The crystal structure of In1.2B3O5.6(OH)1.4
  77. The crystal structure of chlorido(2-(1H-pyrazol-3-yl)phenolato-κ2N,O)(2-(1H-pyrazol-3-yl)phenol-κN)copper(II), C18H15ClCuN4O2
  78. Crystal structure of 1-heptylpyridazin-1-ium iodide, C11H19N2I
  79. The crystal structure of N-butylpyridinium bis(μ2-dichlorido)-tetrachloridodicopper(II), C18H28N2Cu2Cl6
  80. Crystal structure of 6-hydroxy-5-((2-hydroxy-6-oxocyclohex-1-en-1-yl)(4-methoxyphenyl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, C20H22N2O6
  81. Crystal structure of bis(acetonitrile)-diaqua-dichloridoiron(II), C4H10Cl2N2O2Fe
https://doi.org/10.1515/ncrs-2017-0423
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of (E)-1-(4-(((E)-2-hydroxy-5-methylbenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C17H18N2O2
  3. Crystal structure of 1,3,5,7-tetraazaadamantane-1,3-diium 2,5-dicarboxyterephthalate, C16H18N4O8
  4. Crystal structure of guanidinium tetrabutyl-ammonium 5-hydroxyisophthalate dihydrate, C25H50N4O7
  5. Crystal structure of poly[aqua-(μ2-5-methoxyisophthalate-κ3O,O′:O′′)-(μ2-1,4-bis((1H-1,2,4-triazol-1-yl)methyl)benzene-κ2N:N′)nickel(II), NiC21H20N6O6
  6. Crystal structure of aqua-bis(3,4-dimethoxybenzoato-κ1O)-(2,2′-bipyridine-κ2N,N′)copper(II), C28H26CuN2O9
  7. Crystal structure of catena-poly[aqua-(μ2-(3,5-di(1H-imidazol-1-yl)-pyridine-κ2N:N′)-(μ2-2-(carboxylatomethyl)benzoato-κ2O:O′)] cadmium(II), C20H17CdN5O5
  8. The crystal structure of catena-poly[chlorido-(μ2-5-methyl-1,3,4-thiadiazole-2-thiolato-κ2S:N)mercury(II)], C3H3ClHgN2S2
  9. Crystal structure of (E)-2,4-dichloro-6-(((4-methyl-2-nitrophenyl)imino)methyl)phenol, C14H10Cl2N2O3
  10. Crystal structure of a new polymorph of bis[μ-1,3-bis(diphenylphosphino)propane-κ2P:P′-disilver(I)] bis(tetrafluoroborate), [Ag(dppp)]2(BF4)2, C54H52Ag2B2F8P4
  11. The crystal structure of 2-phenyl-4,6-bis(R-tert-butylsulfonamido)-1,3,5-triazine – ethyl acetate (2/1), C38H58N10O6S4
  12. Crystal structure of 6-amino-8-(2-methoxy-phenyl)-2-methyl-2,3,8,8a-tetrahydro-1H-iso-quinoline-5,7,7-tricarbonitrile monohydrate, C20H21N5O2
  13. Crystal structure of methyl (1-phenylethyl)carbamate, C10H13NO2
  14. Crystal structure of dimethanol-(μ2-squarato-κ2O:O′)-tetrakis(tri-p-tolylphosphane-κP)disilver(I) – methanol (1/2), C92H98Ag2O8P4
  15. Crystal structure of catena-poly[bis(μ2-1,4-bis(triazol-1-ylmethyl)benzene-κ2N:N′)-bis(5-tert-butyl-isophthalate-κO)copper(II)]tetrahydrate, C36H46CuN6O12
  16. Crystal structure of 4-aminopyridinium 4-acetyl-(pyridin-4-yl)-1H-1,2,3-triazol-5-olate monohydrate, C14H16N6O3
  17. Crystal structure of 2-(8-bromo-2-phenylimidazo[1,2-α]pyridin-3-yl)-6,7-dimethyl-3-phenylquinoxaline, C29H21BrN4
  18. Crystal structure of aqua(1-(2-pyridyl)ethanone oxime-κ2N,N′)(1-(2-pyridyl)ethanone oximato-κ2N,N′) nitrate monohydrate, C14H19N5O7Cu
  19. Crystal structure of poly[tetraaqua-(μ4-oxalato-κ4O,O′:O′′,O′′′)-(μ8-benzene-1,2,4,5-tetracarboxylato-κ8O1:O2:O3:O4:O5:O6:O7:O8)yttrium(III)], C6H5O8Y
  20. Crystal structure of bis{catena-poly[(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′)silver(I)]} diaqua-bis(5-(4-carboxyphenyl)pyridine-2-carboxylato-κ2N,O)-(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′)disilver(I) octahydrate, C31H35Ag2N4O9
  21. Crystal structure of (E)-N-(2-(benzylamino)-2-oxo-1-(4-oxo-4H-chromen-3-yl)ethyl)-N-(4-bromophenyl)-3-chloroacrylamide hydrate, C27H22BrClN2O5
  22. Crystal structure of catena-poly[octaaqua-bis(μ2-4,6-dicarboxyisophthalate-κ2O:O′)cadmium(II)disodium(I)] dihydrate, C20H28CdNa2O26
  23. Crystal structure of acetonitrile{bis(2-benzimidazolylmethyl)amine-κ3N,N′,N′′}-{maleato-κO}zinc(II) perchlorate - acetonitrile (1/1), C24H24ClN7O8Zn
  24. Crystal structure of 2-amino-4-(3,5-dibromo-4-hydroxyphenyl)-7-methyl-5-oxo-2H,5H-pyrano[4,3-b]pyran-3-carbonitrile, C16H10Br2N2O4
  25. Crystal structure of catena-poly[diaqua-(μ2-3,5-bis(pyridin-4-ylmethoxy)benzoate-κ2N:O) manganese(II)] tetrahydrate [(3,5-bis-(pyridin-4-ylmethoxy)-benzoic-κ1Oκ1N) manganese(II)] trihydrate, C38H42MnN4O14
  26. The crystal structure of 2-carboxybenzaldehyde-2-phenylacetohydrazone, C16H14N2O3
  27. The crystal structure of poly[μ2-aqua-(μ2-2-naphthylamine-1-sulfonato-κ3O,O′:O′′)sodium(I)], C10H10N1O4S1Na
  28. The crystal structure of phthalazin-1(2H)-one, C8H6N2O1
  29. Crystal structure of 3,5-bis(trifluoromethyl)benzyl(Z)-N-(adamantan-1-yl)morpholine-4-carbothioimidate, C24H28F6N2OS
  30. Crystal structure of diazido-bis(μ2-pyridin-2-ylmethanolato-κ2N:O)-bis(pyridin-2-ylmethanolato-κ2N,O)dicobalt(III) – methanol (1/3), C27H35Co2N10O7
  31. Crystal structure of N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(2,2,2-trifluoroethoxy)-2-pyridinesulfonamide, C14H14F3N5O6S
  32. Crystal structure of 1-phenyl-N′-(1-phenyl-5-(thiophen-2-yl)-1H-pyrazole-3-carbonyl)-5-(thiophen-2-yl)-1H-pyrazole-3-carbohydrazide, C28H20N6O2S2
  33. The crystal structure of poly[bis(4-hydroxybenzoato-κO)-(μ2-4,4′-bipyridine-κ2N:N′)copper(II)] hydrate, C24H20N2O7Cu
  34. Crystal structure of poly[μ3-5-(4-(2,6-di(pyridine-2-yl)pyridine-4-yl)phenoxy)isophthalato-κ5O:O′,O′′:N,N′,N′′cobalt(II)], C29H17CoN3O5
  35. Crystal structure of poly[μ3-5-(4-(2,6-di(pyridine-2-yl)pyridine-4-yl)phenoxy)isophthalato-κ6O:O′,O′′:N,N′,N′′)cobalt(II)] C29H17CoN3O5
  36. Crystal structure of diaqua-(acetato-κ3O,O′:O′′)-(μ3-4,6-di(1H-imidazol-1-yl)isophthalato-κ4O:O′:O′′,O′′′)lanthanum(III), C16H15LaN4O8
  37. Synthesis and crystal structure of 6-carboxy-1-(3,5-dicarboxyphenyl)-1H-benzo[d]imidazol-3-ium-5-carboxylate dihydrate, C18H12N2O8
  38. Crystal structure of (E)-2-hydroxybenzaldehyde O-(2-(((E)-(4-(dimethylamino)benzylidene)amino)oxy)ethyl)oxime, C18H21N3O3
  39. Crystal structure of bis{2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}zinc(II), C32H30N4O4Zn
  40. Crystal structure of bis(9-aminoacridin-10-ium) tetrachloridocuprate(II) monohydrate, C26H24Cl4CuN4O
  41. The crystal structure of 4-tert-butyl-N′-[(E)-(4-fluoro-3-methoxyphenyl)methylidene]benzohydrazide, C19H21F1N2O2
  42. Crystal structure of (E)-3-(3-(5-methyl-1-4-tolyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-one, C31H26N8O
  43. Crystal structure of (E)-N′-(4-methoxybenzylidene)-5-methyl-1-(4-tolyl)-1H-1,2,3-triazole-4-carbohydrazide, C19H19N5O2
  44. Crystal structure and molecular packing of O-ethyl (2-chlorophenyl)carbamothioate, C9H10ClNOS
  45. Crystal structure of pyrene-2-carbaldehyde, C17H10O
  46. Crystal structure of (E)-2,4-diiodo-6-(4-methyl-2-nitrostyryl)phenol, C14H10I2N2O3
  47. Crystal structure of (E)-2,4-dichloro-6-(((4-methoxy-2-nitrophenyl)imino)methyl)phenol, C14H10Cl2N2O4
  48. Crystal structure of (E)-2-bromo-4-chloro-6-(4-methoxy-2-nitrostyryl)phenol, C14H10BrClN2O4
  49. Crystal structure of (E)-4,6-diiodo-2-(((4-methoxy-2-nitrophenyl)imino)methyl)-3-methylphenol, C14H10I2N2O4
  50. The crystal structure of 7-bromo-1-cyclopropyl-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid an intermediate of the ozenoxacin synthesis, C14H12BrNO3
  51. Crystal structure of bis(N-(1-(pyrazin-2-yl)ethylidene)nicotinohydrazonato-κ3N,N′,O)copper(II) C24H20N10O2Cu
  52. Crystal structure of diaqua-dinitrato-k2O,O′((Z)-N-((E)-1-(pyrazin-2-yl)ethylidene)nicotinohydrazonato-k3N,N′,O)europium(II), C12H14N7O9Eu
  53. Crystal structure of ethyl 4-amino-5-(5-methyl-1-(4-tolyl)-1H-1,2,3-triazole-4-carbonyl)-2-(phenylamino)thiophene-3-carboxylate, C24H23N5O3S
  54. The crystal structure of acridin-10-ium2-carboxybenzoate, C21H15NO4
  55. The crystal structure of 3-((phenylamino)methylene)-1,5-dioxaspiro[5.5]undecane-2,4-dione, C16H17N1O4
  56. Crystal structure of 12-chloro-5,6,7,12-tetrahydrodibenzo[c,f][1,5]oxastibocine, C14H12ClOSb
  57. Crystal structure of 4-((1,3-dioxoisoindolin-2-yl)methyl)phenethyl 4-methylbenzenesulfonate, C24H21NO5S
  58. Crystal structure of 3-methyl-2,3-dihydro-2-thioxoquinazolin-4(1H)-one, C9H8N2OS
  59. Crystal structure of tert-butyl (2-(4-oxo-2-thioxo-1,4-dihydroquinazolin-3(2H)-yl)ethyl)carbamate, C15H19N3O3S
  60. Crystal structure of ethyl 5-formyl-3,4-dimethylpyrrole-2-carboxylate–1-(propan-2-ylidene)thiosemicarbazide (1/1), C14H22N4O3S
  61. Crystal structure of bis-(N′-(5-ethoxycarbonyl-3,4-dimethyl-pyrrol-2-yl-methylidene)-3-hydroxybenzohydrazide-κ2O,N)copper(II) – dimethylformamide (1/2), C40H50N8O10Cu
  62. Crystal structure of bis(acetato-κO)bis{2-((1H-tetrazol-1-yl)methyl)-1H-benzo[d]imidazole-κN}zinc(II), C22H22N12O4Zn
  63. Crystal structure of 4-phenyl-3-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-1H-1,2,4-triazole-5(4H)-thione, C17H14N6S
  64. Crystal structure of (Z)-N-(4-nitrophenyl)-3-phenyl-3-(phenylamino)acrylamide, C21H17N3O3
  65. Crystal structure of 1,1′-(pentane-1,5-diyl)bis(3-methyl-1H-imidazol-3-ium)bis(hexafluorophosphate), C13H22F12N4P2
  66. Synthesis and crystal structure of bis(furan-2-ylmethanaminium)-catena-[bis(μ2-phthalato-κ2O:O′)cobalt(II)], C26H24CoN2O10
  67. Crystal structure of methyl (R)-4-(o-chlorobenzoyl)-1-thia-4-azaspiro[4.5]decane-3-carboxylate, C17H20ClNO3S
  68. Crystal structure of 2-[[4-[2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl]phenyl] methyl]-1H-isoindole-1,3(2H)-dione, C28H29N3O3
  69. The crystal structure of benzenaminium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate hydrate, C21H19NO8S
  70. Crystal structure of semiconducting potassium poly[(μ2-tetraselenido-κ2Se1:Se4)(μ2-pentaselenido-κ1Se1:Se1)argentate(I)], K3AgSe9
  71. Crystal structure of 2-isopropyl-8-methyl-phenanthrene-3,4-dione, C18H16O2
  72. Crystal structure of 2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione, C19H22O2
  73. Crystal structure of (E)-2-(1-((2-aminophenyl)imino)ethyl)-4-bromophenol, C14H13BrN2O
  74. Crystal structure of 1,1-di(4-cyanophenyl)-2,2-diphenylethene, C28H18N2
  75. Crystal structure of bis(hydroxylamido-κ2O,N)-oxido(1H-pyrazole-3-carboxylato-κ2O,N)vanadium(V), C4H7N4O5V
  76. The crystal structure of In1.2B3O5.6(OH)1.4
  77. The crystal structure of chlorido(2-(1H-pyrazol-3-yl)phenolato-κ2N,O)(2-(1H-pyrazol-3-yl)phenol-κN)copper(II), C18H15ClCuN4O2
  78. Crystal structure of 1-heptylpyridazin-1-ium iodide, C11H19N2I
  79. The crystal structure of N-butylpyridinium bis(μ2-dichlorido)-tetrachloridodicopper(II), C18H28N2Cu2Cl6
  80. Crystal structure of 6-hydroxy-5-((2-hydroxy-6-oxocyclohex-1-en-1-yl)(4-methoxyphenyl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, C20H22N2O6
  81. Crystal structure of bis(acetonitrile)-diaqua-dichloridoiron(II), C4H10Cl2N2O2Fe
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