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Synthesis, crystal structure and optical property of 1,6-bis(p-tolylthio)pyrene, C30H22S2

  • Nie Jing ORCID logo , Wei Jian-Hua and Ni Zhong-Hai EMAIL logo
Published/Copyright: November 2, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 1

Abstract

C30H22S2, triclinic, P1‾ (no. 2), a = 7.5621(2) Å, b = 8.6787(3) Å, c = 9.8951(3) Å, α = 110.4180(10)°, β = 97.6810(10)°, γ = 108.8430(10)°, V = 553.33(3) Å3, Z = 1, Rgt(F) = 0.0413, wRref(F2) = 0.1160, T = 200(2) K.

CCDC no.: 2036234

The molecular structure is shown in the Figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow needle
Size:0.18 × 0.08 × 0.06 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.26 mm−1
Diffractometer, scan mode:Bruker APEX II, φ and ω
θmax, completeness:27.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint:23062, 2535, 0.092
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2191
N(param)refined:147
Programs:Bruker [1], SHELX [2], PLATON [3]
Table 2:

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

AtomxyzUiso*/Ueq
S10.59330 (6)0.46231 (5)0.78017 (5)0.04470 (18)
C10.3410 (2)0.3660 (2)0.68812 (16)0.0317 (3)
C20.2338 (2)0.4693 (2)0.68480 (17)0.0351 (3)
H20.29640.59630.73410.042*
C30.0375 (2)0.3889 (2)0.61058 (17)0.0344 (3)
H3−0.03350.46170.61170.041*
C4−0.0583 (2)0.20304 (19)0.53402 (15)0.0298 (3)
C50.04792 (19)0.09514 (18)0.53799 (14)0.0277 (3)
C60.2490 (2)0.17722 (18)0.61739 (15)0.0288 (3)
C7−0.2596 (2)0.1167 (2)0.45174 (17)0.0338 (3)
H7−0.33110.18790.44780.041*
C8−0.3502 (2)−0.0632 (2)0.37955 (16)0.0327 (3)
H8−0.4838−0.11590.32550.039*
C90.6586 (2)0.6951 (2)0.83391 (17)0.0349 (3)
C100.7003 (2)0.7690 (2)0.73245 (17)0.0400 (4)
H100.68560.69400.63160.048*
C110.7635 (2)0.9525 (2)0.77856 (18)0.0395 (4)
H110.78951.00190.70790.047*
C120.7896 (2)1.0660 (2)0.92575 (17)0.0353 (3)
C130.7460 (3)0.9895 (2)1.02546 (18)0.0433 (4)
H130.76101.06461.12640.052*
C140.6811 (2)0.8063 (2)0.98101 (18)0.0416 (4)
H140.65190.75661.05100.050*
C150.8636 (3)1.2651 (2)0.9741 (2)0.0498 (4)
H15A0.93701.29790.90690.075*
H15B0.94861.32631.07710.075*
H15C0.75341.30100.96990.075*

Source of material

All chemicals were purchased from commercial sources and used as received without further purification. The title compound was prepared by two steps using pyrene as the starting materials. The intermediate 1,6-dibromopyrene was prepared through the bromination of pyrene according to the literature [4]. The title compound was synthesized according to the similar method in the literature [5] and the detailed procedures were displayed as following: Firstly, 3.38 g (24 mmol) of p-methylthiophenol, 3.60 g (10 mmol) of 1,6-dibromopyrene and 80 mL of dimethylformamide (DMF) were added to a 150 mL round bottom flask. The resulting mixture was stirred for 20 min in an ice bath under the protection of nitrogen atmosphere. Secondly, 0.96 g (24 mmol) of NaH (60%) was slowly added to the above flask in batches and the mixture was stirred for 10 min. Then, the mixture was refluxed for 10 h. After the mixture was cooled, light yellow needle-like crystals were obtained directly. Yield: 3.80 g, 86%. The selected suitable single crystal was structurally determined by X-ray diffraction analysis. Melting point: 248–250 °C. 1H NMR (400 MHz, CDCl3) δ (TMS, ppm): 8.74 (s, 2H, J = 8.74 Hz), 8.14–8.03 (m, 6H, J = 8.07 Hz), 7.22–7.20 (m, 4H), 712–7.09 (m, 4H), 2.33 (s, 6H). 13C NMR (400 MHz, CDCl3), δ (TMS, ppm): 136.72, 136.65, 133.13, 133.04, 131.63, 131.40, 131.26, 131.24, 131.15, 130.90, 130.61, 130.46, 130.23, 130.13, 130.07, 128.16, 127.62, 125.56, 125.47, 125.19, 125.04, 21.06. MALDI-TOF MS (m/z): calcd. for C30H22S2 446.1, found 446.1. Elemental analysis – calculated for C30H22S2: C, 80.68%; H, 4.96%; S, 14.36%; found: C, 80.44%, H, 4.88%; S, 14.22%.

Experimental details

All H atoms bound to C atoms were introduced using the HFIX command in the SHELXL-2014 program [2], with the value of 0.93 Å or 0.96 Å for C–H bond distances. All H atoms were allowed for as riding atoms with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C) for hydrogen atoms bonded to pyrene ring and methyl group, respectively. The structure was checked using PLATON [3].

Comment

Organic functional molecules with tunable optical, biological and bifunctional as well as mutifunctional properties have gained great deal of attention due to their potential applications in sensors, live-cell imaging, organic solar cells (OSCs), organic light-emitting diodes (OLEDs) and so on [5], [6], [7], [8], [9], [10], [11]. As one of the most well-known functional molecules, pyrene and its derivatives have been widely investigated by many researchers because of their effectively fluorescent emission, facile synthesis and easy functionalization. Up to date, a great number of pyrene-based derivatives using pyrene as the starting material or as the functional precursor have been reported [12], [13], [14], [15], [16], [17], [18]. However, there are relatively few reports about pyrene-based thioether compounds. Organic functional molecules containing sulfur atoms have also attracted extensive research interest because their special electronic structures may result into special properties, which could develop more novel functional material precursors. Very recently, the crystal structures of pyrene-based thioether compounds such as 1,3,6,8-tetrakis(p-tolylthio)pyrene, 1,8-bis(p-tolylthio)pyrene, 1,6-bis(methylthio)pyrene and so on, have been reported by our group using pyrene as the starting material [5], [19], [20], [21], especially, some of them exhibit relatively excellent fluorescent properties and sensor function for peroxides such as m-chloroperoxybenzoic acid. As a continuation of this work, herein, we report the crystal structure of a new pyrene-based thioether compound which was synthesized in high yield. In addition, the optical property of the title compound was studied preliminarily.

The single X-ray diffraction analysis shows that the crystal structure agrees well with the expected structure of the title compound 1,6-bis(p-tolylthio)pyrene, owing inversion symmetry (see the structure drawing). The pryene core as the main body together with the two side sulfur atoms are almost in a strict plane, whereby the largest deviation for the S1 atom from the main plane is 0.047(3) Å. The thioether bond distances are 1.7725(15) Å for C1-S1 and 1.7729(16) Å for C9-S1, respectively, which are typical Caryl-S bond distances. The C1-S1-C9 bond angle is 103.71°. The bond distances and angles around the sulfur atom in the molecule are comparable to those of its derivatives 1,8-bis(p-tolylthio)pyrene and 1,3,6,8-tetrakis(p-tolylthio)pyrene [5], [19]. The dihedral angle between the pyrene and benzene ring is 81.77(3)°. There exist relatively strong C–H…π interactions between the adjacent pyrenyl unit and the benzene segment, which link the title units into a one-dimensional supramolecular structure (Figure 1).

Figure 1: : The supramolecular structure of the title compound linked by C–H…π interactions.
Figure 1:

: The supramolecular structure of the title compound linked by C–H…π interactions.

The optical property of the title compound was investigated preliminarily. The title compound 1,6-bis(p-tolylthio)pyrene was dissolved in dichloromethane, the absorption is in the range of 325 to 425 nm and a blue emission with peak around 425 nm for the above solution was observed, which are very similar to those of its derivative of 1,8-bis(p-tolylthio)pyrene [5]. The crystal state of the title compound emits green fluorescence with the main peak at 490 nm. Because of its extremely poor solubility, the further sensor property for peroxides has not been carried out.

Corresponding author: Ni Zhong-Hai, School of Chemical Engineering and Technology, China University of Mining and Technology, Xuzhou221116, Jiangsu Province, People’s Republic of China, E-mail:

Funding source: Doctoral Program

Award Identifier / Grant number: JYJBZX19-04

Funding source: National Postdoctoral fund

Award Identifier / Grant number: 2019M652022

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by the Doctoral Program (JYJBZX19-04) and the National Postdoctoral fund (2019M652022).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2020-09-04
Accepted: 2020-10-12
Published Online: 2020-11-02
Published in Print: 2021-01-26

© 2020 Nie Jing et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  59. The crystal structure of 2-iso-propylimidazole, C6H10N2
  60. The crystal structure of aqua-tris (1,3-diphenylpropane-1,3-dionato-κ2O,O′)-lanthanum(III), C45H35LaO7
  61. Crystal structure of (3E,5E)-3,5-bis-4-methoxy-3-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  62. The crystal structure of 3,5-dichloro-6-diazo-2,4-dinitrocyclohexa-2,4-dien-1-one, C6Cl2N4O5
  63. Crystal structure of carbonyl(2-methylquinolin-8-olato-κ2N,O)(triphenylarsine-κAs)rhodium(I), C29H23AsNO2Rh
  64. Crystal structure of (1aS,1a1S,2S)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-yl-4-nitrobenzoate, C22H25NO5
  65. Crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-k2O,O′)(triphenylarsine-κAs)rhodium(I), C24H19AsNO3Rh
  66. Crystal structure of catena-poly[triqua-bis(μ2-4-carboxy-2-(1H-tetrazol-1-yl)-1H-imidazole-5-carboxylato-k3N,O:O′)barium(II)] tetrahydrate, C14H14BaN12O15
  67. Crystal structure of (E)-3′,6′-bis(ethylamino)-2-((quinoxalin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C35H32N6O2
  68. Crystal structure of diaqua-bis(μ2-5-chloro-salicylato-κ3O,O′:O′)-bis(5-chloro-salicylato-κ2O,O′)-bis(1,10-phenanthroline-κ2N,N′) dilead(II) – water (1/2), C52H36C14N4O14Pb2·2(H2O)
  69. Crystal structure of (E)-2-(4-ethoxycarbonyl-3,5-dimethyl-2-(pyrrole-2-ylmethyleneamino)-3′,6′-dihydroxylspiro[isoindoline-1,9′-xanthen]-3-one-methanol (1/1), C31H29N3O7
  70. The crystal structure of 5H-dibenzo[b,e]azepine-6,11-dione, C14H9NO2
  71. Crystal structure of (E)-2-(4-fluoro-2-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  72. The crystal structure of N-(2-methoxy-4,5-bis[phenylselanyl]phenyl)picolinamide, C25H20N2O2Se2
  73. The crystal structure of (E)-2-(5-bromo-2-hydroxybenzylidene)-N-phenylhydrazine-1- carboxamide monohydrate, C14H14BrN3O3
  74. Crystal structure of fac-tricarbonyl-(nitrato-k1O)-bis(pyridine-κN)-rhenium, C13H10O6N3Re
  75. Crystal structure of (E)-2-(((1H-pyrrol-2-yl)methylene)amino)-3′,6′-dihydroxyspiro[isoindoline-1,9′-xanthen]-3-one — methanol (1/2), C27H25N3O6
  76. The crystal structure of 4-amino-N′-(4-aminobenzoyl)benzohydrazide monohydrate, C14H16N4O3
  77. Crystal structure of bis(amino(carbamothioylamino)methaniminium) 5-hydroxyisophthalate monohydrate, C12H20N8O6S2
  78. The crystal structure of 2-(chloromethyl)pyridine, C6H6ClN
  79. The crystal structure of 1-bromo-4-iodo-benzene, C6H4BrI
  80. The crystal structure of 2,6-dimethyl-4-nitro-phenol, C8H9NO3
  81. The crystal structure of 3-chloropropionic acid, C3H5ClO2
  82. The crystal structure of 2-(2-methoxyphenyl)acetic acid, C9H10O3
https://doi.org/10.1515/ncrs-2020-0466
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of 3-oxo-urs-12-en-28-oic acid, C30H46O3·1/6H2O
  4. The crystal structure of (3S,12R,20R,24R)-3,12-diacetyl-20,24-epoxy-dammarane-3,12,25–triol–ethyl acetate (4/1), C34H56O6⋅ 0.25(C4H8O2)
  5. A new polymorph of tetrakis(dimethylammonium) catena-poly[tetrakis(μ2-sulfato-κ2O:O′)dizinc(II)], Zn2C8H32N4O16S4
  6. Crystal structure of 10-oxysophoridine, C15H22N2O2
  7. The crystal structure of (5R,8R,9R,10R,12R,13R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)tetradecahydro-3H-cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O4
  8. Synthesis, crystal structure and optical property of 1,6-bis(p-tolylthio)pyrene, C30H22S2
  9. The crystal structure of hexakis(2-(pyridin-2-ylamino)pyridin-1-ium) decavanadate(V) dihydrate, C60H64N18O30V10
  10. Preparation and crystal structure of a cationic olefin polymerization precatalyst: (1,7-bis(2,6–dichlorophenyl)-1,7-di-aza-4-oxo-heptan-1,4,7-triyl)dimethyl zirconium(IV), C18H20Cl4N2OZr
  11. The crystal structure of fac-tricarbonyl(4,4-dimethyl-2,2-dipyridyl-κ2N,N′)- (pyrazole-κN)rhenium(I) nitrate, C18H16O3N4Re
  12. Synthesis and crystal structure of hexaaquacopper(II) 2,5-dicarboxyterephthalate, C10H16O14Cu
  13. The crystal structure of (8R,10R,12R,14R)- 12-hydroxy-16-(5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)- 4,4,8,10,14-pentamethyltetradecahydro-3H- cyclopenta[a]phenanthrene-3,6(2H)-dione, C30H48O5
  14. Structure of the mixed crystal (S)-(6-(bromo/chloro)-2-methoxy-2,6-dihydroquinolin-3-yl)(phenyl)methanol, C17H14Br0.5Cl0.5NO2
  15. The crystal structure of trans-tetraaqua-bis(4-acetylphenoxyacetato-κ1O)manganese(II), C20H26O12Mn
  16. Crystal structure of (E)-2-(4-fluoro-3-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  17. Crystal structure of DL-α-(methylaminomethyl)benzyl alcohol, C9H13NO
  18. The crystal structure of dipentaerthritol hexanitrate, C10H16N6O19
  19. Crystal structure of N,N-diphenylformamide, C13H11NO
  20. Crystal structure of (E)-2-(3,5-bis(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen- 1(2H)-one, C20H14F6O2
  21. Crystal structure of ortho-methoxy benzaldehyde, C8H8O2 – a second polymorph and deposition of 3D coordinates
  22. Crystal structure of catena-poly[diaqua-bis(μ2-2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O:O')-(2-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoato-κ2O,O')yttrium(III)], C51H79O11Y
  23. Crystal structure of benzylthiouronium chloride, C8H11ClN2S
  24. Synthesis and crystal structure of tert-butyl (2′R,3R,3′R,4a′R,9a′S)-1-acetyl-5-chloro-3″-methyl-2,5″,9′-trioxo-1″-phenyl-1″,4a′,5″,9a′-tetrahydro-1′H,3′H,9′H-dispiro[indoline-3,4′-xanthene-2′,4″-pyrazole]-3′-carboxylate, C36H32ClN3O7
  25. Crystal structure of 2-hydroxy-4-methoxy benzaldehyde, C8H8O3
  26. Crystal structure of poly[diaqua-(m3-3′,5′-dicarboxy-[1,1′-biphenyl]-3,4-dicarboxylato-K4O,O′:O″:O‴) cadmium(II)], C16H11O10Cd
  27. Crystal structure of {tetraaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)}-{triaqua-bis(1-(4-hydroxy-2-oxotetrahydrofuran-3-yl)-2-((4aS,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethane-1-sulfonato-k2O,O') calcium(II)} – water – acetone (1/1/8/2)
  28. Synthesis and crystal structure of bis{2-bromo-6-((E)-((4-((E)-1-(methoxy-imino)ethyl)phenyl)imino)methyl)phenolato- κ2N,O}zinc(II)-methanol(1/2), C65H60Br4N8O9Zn2
  29. Crystal structure of benzenesulphonic acid
  30. Crystal structure of N-benzyl-N-nicotinoyl-nicotine amide C19H15N3O2
  31. Crystal structure of poly[aqua(μ3-2,4-diamino-benzenesulfonato-κ4N:N′,O:O′)silver(I)], C12H18O8N4S2Ag2
  32. Crystal structure of 1,4-bis(methylpyridinium benzene) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C26H18N6NiS4
  33. Crystal structure of the Cu(II) complex chlorido-(6-oxo-2-phenyl-1,6-dihydropyrimidine-4-carboxylato-k2N,O)-(phenanthroline-k2N,N')copper(II), C23H15ClCuN4O3
  34. Crystal structure of phenarsazine chloride acetic acid solvate, C14H13AsClNO2
  35. Crystal structure of poly[aqua-(μ2-3,3′,4,5′-biphenyl tetracarboxylate- κ3O,O′:O′′) -(μ2-4,4′-bis(pyrid-4-yl)biphenyl-κ2N:N′)zinc(II)], C27H18NO9Zn
  36. Crystal structure of catena-poly[(μ2-3-amino-benzenedisulfonato-κ2N:O)-bis (3-methyl-isoquinoline-κN)silver(I)], C26H24N3O3SAg
  37. Crystal structure of 2-((4-Aminophenyl)thio)acetic acid, C8H9NO2S
  38. Crystal structure of phenarsazine chloride dimethylsulfoxide solvate, C14H15AsClNOS
  39. Synthesis and crystal structure of 2-azido-N-phenylacetamide, C8H8N4O
  40. Crystal structure of chlorido{hydridotris[3-phenyl-5-methylpyrazol-1-yl-κN3]borato}copper(II), C30H28BClCuN6
  41. Crystal structure of benzanthrone – a redetermination for correct molecular geometry and localization of hydrogen atoms
  42. Crystal structure of 4-bromobenzaldehyde – complete redetermination at 200 K, C7H5BrO
  43. Crystal structure and spectroscopic properties of chlorido{hydridotris[3-,5-dimethylpyrazol-1-yl-κN3]borato}(3-,5-dimethylpyrazol-1-yl-κN)copper(II), C20H30BClCuN8
  44. The crystal structure of 4-((2-hydroxynaphthalen-1-yl)(pyrrolidin-1-yl)methyl)benzonitrile, C22H20N2O
  45. Crystal structure of 4-ethyl-3-phenylisoquinolin-1(2H)-one, C17H15NO
  46. Crystal structure of (tricyclohexylphosphane-κP)-[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-k1S]gold(I), C26H40AuFNOPS
  47. Crystal structure of (3S,8R,10R,12R,14R)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H54O4
  48. The crystal structure of 2-[(S)-1-(naphthalen-1-yl)ethyl]-2,3,7,7a- tetrahydro-3a,6-epoxyisoindol-1(6H)-one, C19H20NO2
  49. Crystal structure of {hydridotris[3-(t-butyl)-5-isopropylpyrazol-1-yl-κN3]borato}thallium(I), C30H52BN6Tl
  50. Synthesis and crystal structure of 1-octyl-3-phenylquinoxalin-2(1H)-one, C22H26N2O
  51. The crystal structure of 2,6-difluorophenol, C6H4F2O
  52. 4-(9H-Fluoren-9-yl)-4-methylmorpholin-4-ium bromide, C18H20BrNO
  53. The crystal structure of 2,4-dimethylimidazole monohydrate, C5H10N2O
  54. The crystal structure of 1,2-dimethylimidazole, C5H8N2
  55. The crystal structure of 3-ammonio-4-aminobenzoate, C7H8N2O2 – a second polymorph
  56. The crystal structure of 4-hydroxy-2,5-bis(1-methyl-1H-imidazol-3-ium-2-ylthio)-3,6-dioxocyclohexa-1,4-dienolate chloride monohydrate, C14H15N4O5S2Cl
  57. The crystal structure of butyrylferrocene, C14H16FeO
  58. The crystal structure of bi-1,1′-cyclopentane-1,1′-diol, C10H18O2
  59. The crystal structure of 2-iso-propylimidazole, C6H10N2
  60. The crystal structure of aqua-tris (1,3-diphenylpropane-1,3-dionato-κ2O,O′)-lanthanum(III), C45H35LaO7
  61. Crystal structure of (3E,5E)-3,5-bis-4-methoxy-3-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  62. The crystal structure of 3,5-dichloro-6-diazo-2,4-dinitrocyclohexa-2,4-dien-1-one, C6Cl2N4O5
  63. Crystal structure of carbonyl(2-methylquinolin-8-olato-κ2N,O)(triphenylarsine-κAs)rhodium(I), C29H23AsNO2Rh
  64. Crystal structure of (1aS,1a1S,2S)-4a-butoxy-1a,1a1,2,4a,5,6-hexahydro-1H-cyclobuta[de]naphthalen-2-yl-4-nitrobenzoate, C22H25NO5
  65. Crystal structure of carbonyl(2-oxopyridin-1(2H)-olato-k2O,O′)(triphenylarsine-κAs)rhodium(I), C24H19AsNO3Rh
  66. Crystal structure of catena-poly[triqua-bis(μ2-4-carboxy-2-(1H-tetrazol-1-yl)-1H-imidazole-5-carboxylato-k3N,O:O′)barium(II)] tetrahydrate, C14H14BaN12O15
  67. Crystal structure of (E)-3′,6′-bis(ethylamino)-2-((quinoxalin-2-ylmethylene)amino)spiro[isoindoline-1,9′-xanthen]-3-one, C35H32N6O2
  68. Crystal structure of diaqua-bis(μ2-5-chloro-salicylato-κ3O,O′:O′)-bis(5-chloro-salicylato-κ2O,O′)-bis(1,10-phenanthroline-κ2N,N′) dilead(II) – water (1/2), C52H36C14N4O14Pb2·2(H2O)
  69. Crystal structure of (E)-2-(4-ethoxycarbonyl-3,5-dimethyl-2-(pyrrole-2-ylmethyleneamino)-3′,6′-dihydroxylspiro[isoindoline-1,9′-xanthen]-3-one-methanol (1/1), C31H29N3O7
  70. The crystal structure of 5H-dibenzo[b,e]azepine-6,11-dione, C14H9NO2
  71. Crystal structure of (E)-2-(4-fluoro-2-(trifluoromethyl)benzylidene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  72. The crystal structure of N-(2-methoxy-4,5-bis[phenylselanyl]phenyl)picolinamide, C25H20N2O2Se2
  73. The crystal structure of (E)-2-(5-bromo-2-hydroxybenzylidene)-N-phenylhydrazine-1- carboxamide monohydrate, C14H14BrN3O3
  74. Crystal structure of fac-tricarbonyl-(nitrato-k1O)-bis(pyridine-κN)-rhenium, C13H10O6N3Re
  75. Crystal structure of (E)-2-(((1H-pyrrol-2-yl)methylene)amino)-3′,6′-dihydroxyspiro[isoindoline-1,9′-xanthen]-3-one — methanol (1/2), C27H25N3O6
  76. The crystal structure of 4-amino-N′-(4-aminobenzoyl)benzohydrazide monohydrate, C14H16N4O3
  77. Crystal structure of bis(amino(carbamothioylamino)methaniminium) 5-hydroxyisophthalate monohydrate, C12H20N8O6S2
  78. The crystal structure of 2-(chloromethyl)pyridine, C6H6ClN
  79. The crystal structure of 1-bromo-4-iodo-benzene, C6H4BrI
  80. The crystal structure of 2,6-dimethyl-4-nitro-phenol, C8H9NO3
  81. The crystal structure of 3-chloropropionic acid, C3H5ClO2
  82. The crystal structure of 2-(2-methoxyphenyl)acetic acid, C9H10O3
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