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Crystal structure of 2-benzoylpyrene, C23H14O

  • Jing-Yang Li , Bao-Xi Miao , Yun Zhao ORCID logo EMAIL logo and Li-Fang Zhang
Published/Copyright: January 21, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 3

Abstract

C23H14O, monoclinic, P21/c (no. 14), a = 12.931(3) Å, b = 10.486(2) Å, c = 23.004(5) Å, β = 104.80(3)°, V = 3015.6(11) Å3, Z = 8, Rgt(F) = 0.0524, wRref(F2) = 0.1375, T = 123(2) K.

CCDC no.: 1973248

The asymmetric unit of the title crystal 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 block
Size:0.10 × 0.10 × 0.08 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.08 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:24470, 6805, 0.042
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4937
N(param)refined:433
Programs:Bruker programs [1], SHELX [2], [3], PLATON [4]
Table 2:

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

AtomxyzUiso*/Ueq
O11.02634(10)0.63596(12)0.05932(5)0.0394(3)
O20.39545(9)0.65809(10)0.16360(5)0.0310(3)
C10.89505(13)0.78178(16)−0.03752(8)0.0291(4)
H10.94430.8331−0.01120.035*
C20.84704(14)0.82490(17)−0.09496(8)0.0314(4)
H20.86280.9058−0.10690.038*
C30.77541(13)0.74734(17)−0.13462(7)0.0299(4)
H30.74440.7757−0.17350.036*
C40.74977(13)0.62796(16)−0.11677(7)0.0278(4)
H40.70210.5760−0.14370.033*
C50.79525(12)0.58588(16)−0.05874(7)0.0252(3)
H50.77600.5070−0.04630.030*
C60.86977(12)0.66146(15)−0.01898(7)0.0247(3)
C70.93111(13)0.61109(15)0.04071(7)0.0264(4)
C80.87602(12)0.52903(15)0.07645(7)0.0233(3)
C90.93443(12)0.43320(15)0.11275(7)0.0235(3)
H91.00660.42270.11460.028*
C100.88560(12)0.35307(15)0.14632(7)0.0221(3)
C110.94133(13)0.24981(15)0.18197(7)0.0258(4)
H111.01340.23690.18410.031*
C120.89121(13)0.17108(15)0.21247(7)0.0260(4)
H120.92940.10470.23490.031*
C130.78020(12)0.18766(14)0.21105(6)0.0214(3)
C140.72657(14)0.10623(15)0.24147(7)0.0260(4)
H140.76280.03750.26290.031*
C150.61980(14)0.12638(15)0.24019(7)0.0280(4)
H150.58530.07110.26070.034*
C160.56440(13)0.22834(15)0.20850(7)0.0256(3)
H160.49310.24120.20820.031*
C170.61464(12)0.31231(14)0.17699(7)0.0213(3)
C180.55989(12)0.41852(14)0.14357(7)0.0234(3)
H180.48930.43470.14380.028*
C190.60890(12)0.49574(14)0.11162(7)0.0227(3)
H190.57120.56370.09020.027*
C200.71821(12)0.47474(14)0.11011(6)0.0203(3)
C210.77610(12)0.37342(13)0.14490(6)0.0193(3)
C220.72364(12)0.29148(14)0.17779(6)0.0195(3)
C230.76917(12)0.54962(14)0.07546(7)0.0226(3)
H230.73120.61410.05140.027*
C240.19077(13)0.75655(16)0.16691(7)0.0285(4)
H240.18670.68090.14540.034*
C250.10214(14)0.79999(18)0.18448(8)0.0358(4)
H250.03840.75440.17410.043*
C260.10869(15)0.91169(17)0.21756(8)0.0373(4)
H260.04950.94070.22960.045*
C270.20314(16)0.97979(16)0.23253(8)0.0360(4)
H270.20751.05400.25520.043*
C280.29164(14)0.93853(15)0.21414(7)0.0294(4)
H280.35450.98590.22360.035*
C290.28599(13)0.82559(15)0.18135(7)0.0235(3)
C300.37999(12)0.77357(14)0.16249(7)0.0224(3)
C310.45175(12)0.86237(14)0.14061(7)0.0220(3)
C320.55802(12)0.82663(14)0.14633(7)0.0227(3)
H320.58430.75260.16720.027*
C330.62512(12)0.90006(14)0.12123(7)0.0223(3)
C340.73496(13)0.86572(15)0.12655(7)0.0269(4)
H340.76390.79520.14950.032*
C350.79679(13)0.93451(16)0.09866(7)0.0295(4)
H350.86720.90960.10240.035*
C360.75620(13)1.04472(15)0.06350(7)0.0261(4)
C370.81766(14)1.11643(16)0.03352(7)0.0306(4)
H370.88781.09190.03610.037*
C380.77661(14)1.22294(16)0.00013(7)0.0318(4)
H380.81901.2688−0.01960.038*
C390.67228(14)1.26176(15)−0.00403(7)0.0290(4)
H390.64561.3340−0.02630.035*
C400.60674(13)1.19341(14)0.02488(7)0.0244(3)
C410.49800(14)1.22880(15)0.02096(7)0.0260(4)
H410.47001.3013−0.00070.031*
C420.43494(13)1.15951(15)0.04796(7)0.0246(3)
H420.36461.18470.04420.030*
C430.47546(12)1.04783(14)0.08230(6)0.0208(3)
C440.58303(12)1.01110(14)0.08764(6)0.0214(3)
C450.64898(13)1.08363(14)0.05884(7)0.0228(3)
C460.41177(12)0.97325(14)0.10963(7)0.0225(3)
H460.34170.99800.10710.027*

Source of material

The title compound 2-benzoylpyrene was obtained by two steps using 4,5,9,10-tetrahydrogenpyrene as the starting materials. The educt 4,5,9,10-tetrahydrogenpyrene was prepared according to the previous literature [5]. The whole synthetic procedures were refered to the method reported recently by Zhang et al. [6]. The detailed synthetic processes are described as following. 4,5,9,10-tetrahydrogenpyrene (7 mmol) was dissolved in carbon disulfide (100 mL) and then anhydrous aluminum chloride (14 mmol) was added under nitrogen atmosphere. The mixture was kept below 0 °C and stirred for 30 min. Then it was added dropwise into a solution of benzoyl chloride (7.4 mmol) in carbon disulfide (20 mL), and the mixture was stirred at room temperature for 10 h. After the reaction completed, the mixture was poured into 150 mL ice water and stirred overnight. The mixture was extracted with dichloromethane three times and the collected organic layer was combined, washed with brine twice and dried over anhydrous magnesium sulfate. The crude product was condensed and purified on a silica-gel column using a mixture of dichloromethane and hexane as eluent, yielding the intermediate 2-benzoyl-4,5,9,10-tetrahydropyrene as a yellow needle-like crystal (Yield: 87%). 1H NMR (400 MHz, CDCl3) δ 7.90–7.82 (m, 2H), 7.62 (dd, J = 10.5, 4.3 Hz, 1H), 7.54 (dd, J = 15.2, 7.4 Hz, 4H), 7.22 (dd, J = 8.2, 6.6 Hz, 1H), 7.14 (d, J = 7.4 Hz, 2H), 2.96 (s, 8H). MS: (C23H18O) m/z 310(M+, 100), 233(58), 202(30), 105(32).

The preparative method of the title compound as follows. A solution of 2-benzoyl-4,5,9,10-tetrahydropyrene (5 mmol) and DDQ (2,3-dichloro-5,6-dicyano-1,4-benzochinone, 11 mmol) in dry toluene (50 mL) were heated at reflux under nitrogen atmosphere for 24 h. The mixture was cooled to room temperature and filtered. The filtrate was washed with 5% aqueous sodium hydroxide and water and dried over anhydrous magnesium sulfate. The crude product was purified on a silica-gel column using a mixture of dichloromethane and hexane as eluent, yielding light yellow block-like crystals (Yield: 73%). A suitable block single crystal of the compound for X-ray crystallography was obtained by the slow evaporation of a mixture of dichloromethane/hexane at room temperature. 1H NMR (400 MHz, CDCl3) δ 8.62 (s, 2H), 8.25 (d, J = 7.7 Hz, 2H), 8.15 (s, 4H), 8.10 (t, J = 7.6 Hz, 1H), 8.01–7.94 (m, 2H), 7.73 C 7.65 (m, 1H), 7.59 (t, J = 7.6 Hz, 2H). MS: (C23H14O) m/z 306(M+, 100), 229(25), 201(60), 105(20), 77(28).

Experimental details

All H atoms were introduced using the HFIX commond in the SHELXL program [3], with the value of 0.93 Å for C—H bonds distances. All H atoms were allowed for as riding atoms with Uiso(H) = 1.2Ueq(C) for all hydrogen atoms. The structure was checked using PLATON [4].

Comment

Organic optoelectronic materials such as organic light emitting diodes (OLEDs), organic photovoltaic cells (OPV), organic field-effect transistors (OFETs), fluorescent probe, etc. [7]. have aroused much attentions in several fields. Up to date, there are several tens of important functional precursors for the design, synthesis of interesting new organic optoelectronic materials [8]. As one of the well-known starting functional material, new pyrene-based organic functional compounds have been paid everlasting attentions due to not only their excellent photophysical properties, but also theirs precursor pyrene easy obtained from coal tar as the huge side product of coal coking. For example, the pyrene-based derivatives OLED has been wide application and broad prospects, because some pyrene-based derivatives are easier to make thinner, lighter, flexible and large-area sheets [9], [10]. In addition, pyrene-based derivatives also have been widely employed in fluorescent probes with low detection limit and high sensitivity characteristics due to pyrene-based fluorescent probes usually exhibit high solution fluorescence quantum yield and large Stokes shift [11], [12]. But most of the reported pyrene-based derivatives are 1-monosubstituted compounds and 1,3,6,8-tetrasubstituted compounds because 1-, 3-, 6-, 8-positions are commonly active sites of pyrene for nucleophilic substitution reaction. The research on inactive sites such as 2-, 7-position of pyrene recently arouse the interest of scientists [13], which can bring new pyrene-based functional materials with interesting optoelectronic properties. It is very hard to directly obtain 2-, 7-position substituted and pyrene-based derivatives from pyrene, therefore, the 2-substituted and 2,7-disubstituted pyrene-based derivatives are still very limited. Zhang et al. [6], [10] have reported the synthesis and crystal structure of one benzoylpyrene with 4-methylbenzoyl group at the 2-position of pyrene via three steps using pyrene as the starting material.

The single crystal X-ray diffraction analysis results are consistent with expectation. There are two independent 2-benzoylpyrene molecules in the crystal structure. The crystal structure indicates that the benzoyl group is bonded to the 2-position of the pyrene precursor. The functional group C—O bond length is 1.2241(19) Å for C7—O1 and 1.2265(18) Å for C30—O2 in the two 2-benzoylpyrene molecules, respectively, which conforms to the typical characteristics of the carbonyl C—O double bond. The bond angles around the carbonyl group in the two independent 2-benzoylpyrene molecules are 119.73(15)° for C6—C7—O1 and 119.65(14)° for O2—C30—C29. All the sixteen carbon atoms of pyrene moiety are located on a nearly strict plane with the largest derivation of 0.073(2) Å for C8 and 0.063(2) Å for C31 from the mean plane. The dihedral angel between the pyrene ring and the phenyl moieties are 65.43(15)° and 65.51(15)° in the two molecules, respectively. All molecular geometric parameters of both crystallographically independent are in the expected ranges [14]. There are many interactions in the crystal of the title compound. Firstly, there exist strong π-π interactions between the neighboring pyrene rings with the shortest C—C distance of 3.382 Å, forming dimeric supramolecular substructures. Then, these dimeric substructures are linked together by C—H⋯O hydrogen bonds, giving a one-dimensional zizag-like supramolecular structure. Finally, a three-dimensional network supramolecular structure is obtained based on the above one-dimensional zizag-like supramolecular structures linked by C—H–π interactions from the adjacent pyrene rings and benzene rings.

Acknowledgements

This work was supported by Science and Technology Project of Xuzhou (No. KC19007) and the Open Sharing Fund for the Large-scale Instruments and Equipments of CUMT.

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Received: 2019-10-24
Accepted: 2019-12-20
Published Online: 2020-01-21
Published in Print: 2020-04-28

©2020 Jing-Yang Li et al., published by De Gruyter, Berlin/Boston

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

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  43. Crystal structure of 4-(3-fluorophenyl)-7-hydroxy-2H-chromen-2-one, C15H9FO3
  44. Crystal structure of (E)-2-((2-(pyrimidin-2-yl)hydrazono)methyl)quinolin-1-ium perchlorate – methanol (1/1), C15H16N5O5Cl
  45. The crystal structure of bis(N-(amino(pyridin-2-yl)methylene)-5-chloro-2-hydroxybenzohydrazonato-κ3N,N′,O)zinc(II) – methanol (2/5), C57H60Cl2N16O13Zn2
  46. Synthesis and crystal structure of 4,4′-di(4-pyridyl)-6,6′-di(tert-butyl)-2,2′-[propylenedioxybis(nitrilomethylidyne)]diphenol, C35H40N4O4
  47. Crystal structure of (3E,3′E)-3,3′-((1,3,4-thiadiazole-2,5-diyl)bis(sulfanediyl))bis(4-hydroxy-4-phenylbut-3-en-2-one), C22H18N2O4S3
  48. Crystal structure of (N-benzyl-N-methyl-dithiocarbamato-κ2S,S′)di(4-chlorobenzyl)chloridotin(IV), C23H22Cl3NS2Sn
  49. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) sodium bromide hydrate, [Na(18-crown-6)]Br ⋅ H2O, C12H26BrNaO7
  50. Crystal structure of 7-ethoxyl-6,8-difluoro-4-oxo-1-phenyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H13F2N1O4
  51. Crystal structure of chlorido (2-(4-ethylphenyl)pyrimidine-k2C,N)(triphenylphosphane-kP) palladium(II), C30H26ClN2PPd
  52. Crystal structure of 18-crown-6 – 1,4-diiodotetrafluorobenzene – acetonitrile (1/1/2), C22H30F4I2N2O6
  53. Crystal structure of diisobutyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C16H24O6
  54. Crystal structure of poly[[tris(μ2-cis-1,2-cyclohexanedicarboxylato)-κ2O, O′]-bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N, N′,N′′]-trizinc(II)] – water (1/20), C60H106N12O32Zn3
  55. The synthesis and crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxamide–tetrahydrofuran (1/1), C16H14N4Cl2F6O3S
  56. Crystal structure of dimethylbis(diisopropyldithiocarbamato-κ2S,S′)tin(IV), C16H34N2S4Sn
  57. Crystal structure of diisopropyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C14H20O6
  58. The synthesis and crystal structure of ethyl (E)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-((2-methoxybenzylidene)amino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C22H15N3Cl2F6O4S
  59. The crystal structure of a matrine derivative, 13-(methylamine-1-yl) carbodithioate matrine, C17H27N3OS2
  60. Crystal structure of bis(2-hydroxy-6-((phenylimino)methyl)phenolato-κ2N,O)copper(II), C26H20CuN2O4
  61. The crystal structure of 2-p-fluorophenyl-5-dihydroxymethyl-1,3,4-oxadiazole, C9H7FN2O3
  62. Crystal structure of dichloridobis(4-chlorophenyl-κC1)(1,10-phenanthroline-κ2N,N′)tin(IV), C24H16Cl4N2Sn
  63. Crystal structure of bis{bromido-triphenyltin(IV)}(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′), C46H38Br2N2O2Sn2
  64. Crystal structure of 2-(5-chloro-quinolin-8-yloxy)-N-quinolin-8-yl-acetamide, C20H14N3O2Cl
  65. Crystal structure of bis(N-(1-(3-ethylpyrazin-2-yl)ethylidene)-3-hydroxy-2-naphthohydrazonato-κ3N,N′,O)cobalt(II) — dimethylformamide (1/1), C41H41N9O5Co
  66. Crystal structure of bis[2-(1-(3-ethylpyrazin-2-yl)ethylidene)-1-tosylhydrazin-1-ido-κ3-N,N′,O]copper(II), C30H34N8O4S2Cu
  67. Crystal structure of (2-p-tolylpyrimidine-κ2C,N)(triphenylphosphane-κP) palladium(II), C29H24ClN2PPd
  68. Halogen bonding in crystal structure of bis(1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium triiodide, C16H32CsI3O8
  69. The synthesis and crystal structure of N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazol-5-yl)-2-phenylacetamide, C20H10N4Cl2F6O2S
  70. The crystal structure of 4-(trifluoromethyl)nicotinic acid, C7H4F3NO2
  71. Crystal structure of 3-(2-methylbenzyl)thiazolidin-2-one, C11H13ONS
  72. The crystal structure of 2,2,2-trifluoro-1-(isoquinolin-1-yl)ethane-1,1-diol, C11H8F3NO2
  73. The crystal structure of 3-bromoisonicotinic acid, C6H4BrNO2
  74. The crystal structure of 5-nitropicolinic acid monohydrate, C6H6N2O5
  75. The crystal structure of 3-(4-hydroxybenzyl)-1,5-dioxaspiro[5.5]undecane-2,4-dione, C16H18O5
  76. Crystal structure of [[Mo3Se7(S2CNEt2)3]2(μ-Se)] ⋅ 2(C6H4Cl2), C42H68Cl4Mo6N6S12Se15
  77. Crystal structure of (E)-4-hydroxy-3-((5-phenyl-1,3,4-oxadiazol-2-yl)thio)pent-3-en-2-one, C13H12N2O3S
  78. The crystal structure of (2,3-dioxo-5,6:13,14-dibenzo-9,10-benzo-1,4,8,11-7, 11-diene-κ4N,N′,N′′,N′′′)-nickel(II), Ni(C22H14N4O2)
  79. Crystal structure of 3-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-ylthio)-propanoic acid, C15H17N3O4S
  80. The crystal structure of dichlorobis(2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl) palladium(II)-dichloroform, C68H100Cl8P2Pd
  81. Crystal structure and antimicrobial properties of (1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium(I) pentaiodide, C16H32CsI5O8
https://doi.org/10.1515/ncrs-2019-0790
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of catena-poly[(μ2-3-(benzo[d]thiazol-2-yl)-5-carboxybenzoato-κ2N:O)silver(I)], C15H8AgNO4S
  3. Crystal structure of bis(4-phenylpiperazin-1-ium) bis(2-(4-phenylpiperazin-1-yl)succinato-κ2O,O′)copper(II) tetrahydrate, C48H70CuN8O12, [C10H14N2]2[Cu(C14H17N2O4)2] ⋅ 4 H2O
  4. Crystal structure of triaqua-bis(2-(6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)-1-(2-oxo-2,5-dihydrofuran-3-yl)ethane-1-sulfonato-κ2O,O′)calcium(II) – ethanol (1/2), C44H76CaO19S2
  5. The crystal structure of ethyl 5-(4-(diphenylamino)phenyl)thiophene-2-carboxylate, C25H21NO2S
  6. The crystal structure of 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine, C7H6BrN5
  7. The crystal structure of (E)-5-chloro-2-hydroxy-N′-(2-hydroxy-4-methoxybenzylidene)benzohydrazide, C15H13ClN2O4
  8. The crystal structure of (2Z,2′Z)-N′,N′′′′-(pyridine-2,6-dicarbonyl)dipicolinohydrazonamide, C19H17N9O2
  9. Photochromic properties and crystal structure of 3,3′-(perfluorocyclopent-1-ene-1,2-diyl)bis(5-(4-(azidomethyl)phenyl)-2-methylthiophene), C29H20F6N6S2
  10. Crystal structure of aqua-dichlorido-(4-(((3-ethoxy-2-oxidobenzylidene)hydrazono)(oxido)methyl)pyridin-1-ium-κ3N,O,O′)iron(III), C15H16Cl2N3O4Fe
  11. Crystal structure of catena-poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)-bis(2,3,4,5-tetrabromo-6-carboxybenzoato-κ1O)-nickel(II)], C26H14Br8NiN2O10
  12. Crystal structure of diethanol-κ1O-bis(μ2-N-((2-oxidonaphthalen-1-yl)methylene)pyrazine-2-carbohydrazonato-κ5N,O,O′:O′:N′)-bis(nitrato-κ2O,O′)dieuropium(III), C36H32N10O12Eu2
  13. The crystal structure of 2-aminoisophthalic acid, C8H7NO4
  14. Crystal structure of (E)-2-(4-((3,4-difluorobenzyl)oxy)styryl)-4,6-dimethoxybenzaldehyde, C24H20F2O4
  15. Crystal structure of 2-benzoylpyrene, C23H14O
  16. Crystal structure of chlorido-(η6-p-cymene)-(N-(2-fluorophenyl)-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) – acetone (1/1), C22H23ClN2F7OPRu
  17. The crystal structure of 2-bromoisonicotinic acid, C6H4BrNO2
  18. Crystal structure of 1,3,5,7-tetraphenyl-8-(N-phenylformamido)-2-oxa-5-azabicyclo[4.2.0]oct -3-en-7-yl benzoate, C44H34N2O4
  19. Synthesis and crystal structure of 4-(3-acetyl-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)-7-(diethylamino)-2H-chromen-2-one, C21H21N3O4S
  20. Crystal structure of poly[diaqua-(μ2-4,4′-bipyridine-κ2N:N′)-(μ2-3,4,5,6-tetrafluorophthalato-κ2O:O′)nickel(II)], C18H12F4NiN2O6
  21. Crystal structure of 4-hydroxynaphtho[2,3-b]benzofuran-6,11-dione, C16H8O4
  22. The crystal structure of 3,10-bis(4-methoxyphenyl)-6,12-dibenzyl-2,9-acetyl-6,12-diazapentacyclo[6.3.1.02,7.04,11.05,9]dodecane – acetone (1/1), C45H48N2O5
  23. The crystal structure of (E)-2-(((2-(1H-indol-3-yl)ethyl)iminio)methyl)-6-bromophenolate, C17H15N2BrO
  24. Crystal structure of catena-poly[diaqua-(μ2-oxalyl dihydrazide-κ4N,O:N′,O′)-bis(μ2-pyridine-2,3-dicarboxylato-κ3N,O,O′)dicadmium(II)] hexahydrate, C16H28O18N6Cd2
  25. Crystal structure of poly[tetra-(μ4-naphthalene-1,8-dicarboxylato-κ4O:O,O′: O′′:O′′,O′′′)-(μ4-oxo-κ4O:O:O:O) penta-lead(II)], C48H24O17Pb5
  26. Crystal structure of 5H-dibenzo[c,f][1,5]oxabismocin-12 (7H)-yl acetate, C16H15O3Bi
  27. The crystal structure of 2-(4-chloro-6-nitrophenyl)-1-(4-chloro-3-nitrophenyl)diazene 1-oxide, C12H6Cl2N4O5
  28. Crystal structure of bis(3-methyl-N-(1-(pyrazin-2-yl)ethylidene)benzohydrazonato-κ3O,N,N′)nickel(II), C28H26N8O2Ni
  29. Crystal structure of 3,10-bis(4-chlorophenyl)-6,12-dibenzyl-2,9-acetyl-6,12-diazapentacyclo[6.3.1.02,7.04,11.05,9]-dodecane, C40H36Cl2N2O2
  30. Crystal structure of bis[(μ2-4⋯O,O′:O′)-(4-hydroxybenzoato-κ2O,O′)-(1,10-phenanthroline-κ2N,N′)]-di-lead(II)μ-4-hydroxybenzoato-κ3O,O′:O′;κ3O,O′:O′-bis-[(4-hydroxybenzoato-κ2O,O′)bis(1,10-phenanthroline-κ2N,N′)di-lead(II)] monohydrate, C52H36N4O12Pb2 ⋅ H2O
  31. Crystal structure of poly[diaqua-(μ3-3,4,5,6-tetrafluoro-phthalato-κ3O:O′:O′′)-(μ2-1,2-bis(4-pyridyl)ethene-κ2N:N′)cobalt(II)], C14H9CoF4NO6
  32. Crystal structure of 7-hydroxy-4-phenyl-2H-chromen-2-one, C15H10O3
  33. Crystal structure of 3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione 4-hydroxybenzoic acid, C20H24N4O6
  34. Crystal structure of catena-poly[(μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O)-bis(nitrato-κ1O)zinc(II)], C17H16N6O7Zn
  35. The crystal structure of diaqua-bis(6-aminopicolinato-κ2N,O)magnesium(II), C12H14O6N4Mg
  36. Crystal structure of (pyridine-2-carboxamide-κ2N,O)-[tris((1H-benzo[d]imidazol-2-yl)methyl)amine-κ4N,N′,N′′,N′′′]nickel(II) diperchlorate — methanol (1/3), C33H39Cl2N9NiO12
  37. Crystal structure of catena-poly[diaqua-bis(3-(4-trifluoromethyl-phenyl)-acrylato-κO1)-(μ2-1,4-bis(1-imidazolyl)benzene-κ2N3:N3′)cobalt(II)], C32H26CoF6N4O6
  38. Crystal structure of (E)-3-(2-(2-hydroxy-4-methoxystyryl)-3,3-dimethyl-3H-indol-1-ium-1-yl)propane-1-sulfonate monohydrate, C22H25NO5S⋅H2O
  39. The crystal structure of bis(N-oxy-2-(1H-tetrazol-1-yl) acetamide κ2O,O′)-diaqua-zinc(II), C6H12ZnN10O6
  40. Crystal structure of (E)-4-((4-chlorophenylimino)methyl)pyridinium 3,5-dinitrobenzoate, C19H13ClN4O6
  41. Crystal structure of dichlorido-bis((E)-2-((pyridin-4-ylmethylene)amino)phenol)zinc(II), C24H20Cl2N4O2Zn
  42. Crystal structure of cyclo-[tetrachlorido-bis(μ2-p-xylylenediamine-κ2N:N′)dipalladium(II)] dimethyl sulfoxide solvate, C20H36Cl4N4O2Pd2S2
  43. Crystal structure of 4-(3-fluorophenyl)-7-hydroxy-2H-chromen-2-one, C15H9FO3
  44. Crystal structure of (E)-2-((2-(pyrimidin-2-yl)hydrazono)methyl)quinolin-1-ium perchlorate – methanol (1/1), C15H16N5O5Cl
  45. The crystal structure of bis(N-(amino(pyridin-2-yl)methylene)-5-chloro-2-hydroxybenzohydrazonato-κ3N,N′,O)zinc(II) – methanol (2/5), C57H60Cl2N16O13Zn2
  46. Synthesis and crystal structure of 4,4′-di(4-pyridyl)-6,6′-di(tert-butyl)-2,2′-[propylenedioxybis(nitrilomethylidyne)]diphenol, C35H40N4O4
  47. Crystal structure of (3E,3′E)-3,3′-((1,3,4-thiadiazole-2,5-diyl)bis(sulfanediyl))bis(4-hydroxy-4-phenylbut-3-en-2-one), C22H18N2O4S3
  48. Crystal structure of (N-benzyl-N-methyl-dithiocarbamato-κ2S,S′)di(4-chlorobenzyl)chloridotin(IV), C23H22Cl3NS2Sn
  49. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) sodium bromide hydrate, [Na(18-crown-6)]Br ⋅ H2O, C12H26BrNaO7
  50. Crystal structure of 7-ethoxyl-6,8-difluoro-4-oxo-1-phenyl-1,4-dihydro-quinoline-3-carboxylic acid, C18H13F2N1O4
  51. Crystal structure of chlorido (2-(4-ethylphenyl)pyrimidine-k2C,N)(triphenylphosphane-kP) palladium(II), C30H26ClN2PPd
  52. Crystal structure of 18-crown-6 – 1,4-diiodotetrafluorobenzene – acetonitrile (1/1/2), C22H30F4I2N2O6
  53. Crystal structure of diisobutyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C16H24O6
  54. Crystal structure of poly[[tris(μ2-cis-1,2-cyclohexanedicarboxylato)-κ2O, O′]-bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N, N′,N′′]-trizinc(II)] – water (1/20), C60H106N12O32Zn3
  55. The synthesis and crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxamide–tetrahydrofuran (1/1), C16H14N4Cl2F6O3S
  56. Crystal structure of dimethylbis(diisopropyldithiocarbamato-κ2S,S′)tin(IV), C16H34N2S4Sn
  57. Crystal structure of diisopropyl 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylate, C14H20O6
  58. The synthesis and crystal structure of ethyl (E)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-((2-methoxybenzylidene)amino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C22H15N3Cl2F6O4S
  59. The crystal structure of a matrine derivative, 13-(methylamine-1-yl) carbodithioate matrine, C17H27N3OS2
  60. Crystal structure of bis(2-hydroxy-6-((phenylimino)methyl)phenolato-κ2N,O)copper(II), C26H20CuN2O4
  61. The crystal structure of 2-p-fluorophenyl-5-dihydroxymethyl-1,3,4-oxadiazole, C9H7FN2O3
  62. Crystal structure of dichloridobis(4-chlorophenyl-κC1)(1,10-phenanthroline-κ2N,N′)tin(IV), C24H16Cl4N2Sn
  63. Crystal structure of bis{bromido-triphenyltin(IV)}(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′), C46H38Br2N2O2Sn2
  64. Crystal structure of 2-(5-chloro-quinolin-8-yloxy)-N-quinolin-8-yl-acetamide, C20H14N3O2Cl
  65. Crystal structure of bis(N-(1-(3-ethylpyrazin-2-yl)ethylidene)-3-hydroxy-2-naphthohydrazonato-κ3N,N′,O)cobalt(II) — dimethylformamide (1/1), C41H41N9O5Co
  66. Crystal structure of bis[2-(1-(3-ethylpyrazin-2-yl)ethylidene)-1-tosylhydrazin-1-ido-κ3-N,N′,O]copper(II), C30H34N8O4S2Cu
  67. Crystal structure of (2-p-tolylpyrimidine-κ2C,N)(triphenylphosphane-κP) palladium(II), C29H24ClN2PPd
  68. Halogen bonding in crystal structure of bis(1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium triiodide, C16H32CsI3O8
  69. The synthesis and crystal structure of N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazol-5-yl)-2-phenylacetamide, C20H10N4Cl2F6O2S
  70. The crystal structure of 4-(trifluoromethyl)nicotinic acid, C7H4F3NO2
  71. Crystal structure of 3-(2-methylbenzyl)thiazolidin-2-one, C11H13ONS
  72. The crystal structure of 2,2,2-trifluoro-1-(isoquinolin-1-yl)ethane-1,1-diol, C11H8F3NO2
  73. The crystal structure of 3-bromoisonicotinic acid, C6H4BrNO2
  74. The crystal structure of 5-nitropicolinic acid monohydrate, C6H6N2O5
  75. The crystal structure of 3-(4-hydroxybenzyl)-1,5-dioxaspiro[5.5]undecane-2,4-dione, C16H18O5
  76. Crystal structure of [[Mo3Se7(S2CNEt2)3]2(μ-Se)] ⋅ 2(C6H4Cl2), C42H68Cl4Mo6N6S12Se15
  77. Crystal structure of (E)-4-hydroxy-3-((5-phenyl-1,3,4-oxadiazol-2-yl)thio)pent-3-en-2-one, C13H12N2O3S
  78. The crystal structure of (2,3-dioxo-5,6:13,14-dibenzo-9,10-benzo-1,4,8,11-7, 11-diene-κ4N,N′,N′′,N′′′)-nickel(II), Ni(C22H14N4O2)
  79. Crystal structure of 3-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-ylthio)-propanoic acid, C15H17N3O4S
  80. The crystal structure of dichlorobis(2-(dicyclohexylphosphino)-2′,4′,6′-tri-i-propyl-1,1′-biphenyl) palladium(II)-dichloroform, C68H100Cl8P2Pd
  81. Crystal structure and antimicrobial properties of (1,4,7,10-tetraoxacyclododecane-κ4O,O′,O′′,O′′′)cesium(I) pentaiodide, C16H32CsI5O8
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