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Crystal structure of 2-acetyl pyrene, C18H12O

  • Yun-Hui Xu EMAIL logo , Bao-Xi Miao and Ran Zhang
Published/Copyright: December 5, 2018
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 2

Abstract

C18H12O, triclinic, P1̄ (no. 2), a = 8.0788(16) Å, b = 8.1221(16) Å, c = 18.162(4) Å, α = 91.01(3)°, β = 94.62(3)°, γ = 92.80(3)°, V = 1186.2(4) Å3, Z = 4, Rgt(F) = 0.0415, wRref(F2) = 0.1044, T = 293(2) K.

CCDC no.: 1877283

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow block
Size:0.12 × 0.10 × 0.09 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°, >96%
N(hkl)measured, N(hkl)unique, Rint:9811, 5236, 0.030
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3554
N(param)refined:345
Programs:Bruker programs [1], SHELX [2], PLATON [3]
Table 2:

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

AtomxyzUiso*/Ueq
O0.42960(11)0.38553(12)0.30956(5)0.0376(3)
C10.28051(16)0.40460(14)0.29848(7)0.0242(3)
C20.18566(17)0.33315(16)0.23005(7)0.0320(3)
H2A0.14670.42080.19950.048*
H2B0.09250.26560.24350.048*
H2C0.25710.26730.20330.048*
C30.19304(14)0.50183(14)0.35263(6)0.0204(3)
C40.02616(15)0.53773(14)0.34070(6)0.0213(3)
H4−0.03450.50010.29750.026*
C5−0.05170(14)0.62978(13)0.39294(6)0.0193(3)
C6−0.22224(14)0.67189(14)0.38139(7)0.0232(3)
H6−0.28480.63610.33830.028*
C7−0.29334(14)0.76301(14)0.43230(7)0.0237(3)
H7−0.40360.78970.42310.028*
C8−0.20320(14)0.81921(13)0.49988(7)0.0207(3)
C9−0.27348(15)0.91417(14)0.55333(7)0.0244(3)
H9−0.38410.94100.54580.029*
C10−0.18043(16)0.96841(14)0.61703(7)0.0261(3)
H10−0.22901.03200.65170.031*
C11−0.01602(15)0.92960(14)0.63003(7)0.0240(3)
H110.04460.96760.67320.029*
C120.05997(15)0.83398(13)0.57906(6)0.0200(3)
C130.22973(15)0.79079(14)0.59050(7)0.0222(3)
H130.29160.82480.63400.027*
C140.30195(14)0.70170(14)0.53955(7)0.0213(3)
H140.41250.67590.54860.026*
C150.21154(14)0.64613(13)0.47181(6)0.0184(3)
C160.28345(14)0.55645(13)0.41794(6)0.0203(3)
H160.39480.53220.42560.024*
C170.04138(14)0.68408(13)0.45911(6)0.0174(3)
C18−0.03427(14)0.77894(13)0.51280(6)0.0178(3)
O20.98724(12)0.39056(11)−0.11701(5)0.0375(3)
C190.94771(15)0.24356(16)−0.12047(7)0.0253(3)
C200.97948(16)0.14184(16)−0.18766(7)0.0306(3)
H20A1.04050.2084−0.22040.046*
H20B0.87530.1029−0.21260.046*
H20C1.04290.0495−0.17270.046*
C210.86550(14)0.16276(14)−0.05876(6)0.0215(3)
C220.81227(14)−0.00294(14)−0.06272(6)0.0217(3)
H220.8299−0.0656−0.10450.026*
C230.73298(14)−0.07711(14)−0.00534(6)0.0204(3)
C240.68088(15)−0.24882(15)−0.00707(7)0.0249(3)
H240.6988−0.3138−0.04810.030*
C250.60640(15)−0.31797(15)0.04964(7)0.0256(3)
H250.5755−0.42990.04710.031*
C260.57390(14)−0.22296(14)0.11365(6)0.0215(3)
C270.49717(15)−0.29220(15)0.17318(7)0.0264(3)
H270.4658−0.40400.17190.032*
C280.46770(15)−0.19600(16)0.23379(7)0.0271(3)
H280.4160−0.24370.27270.033*
C290.51423(14)−0.02933(16)0.23735(7)0.0253(3)
H290.49190.03380.27830.030*
C300.59444(14)0.04514(14)0.18010(6)0.0214(3)
C310.65270(15)0.21562(15)0.18326(7)0.0253(3)
H310.63400.28080.22410.030*
C320.73406(15)0.28286(14)0.12800(7)0.0245(3)
H320.77300.39250.13230.029*
C330.76171(14)0.18907(14)0.06277(6)0.0207(3)
C340.84056(14)0.25702(14)0.00396(7)0.0224(3)
H340.87720.36750.00660.027*
C350.70488(13)0.01993(14)0.05784(6)0.0185(3)
C360.62354(13)−0.05232(14)0.11713(6)0.0194(3)

Source of material

The title complex was prepared by two steps. The intermediate 2-acetyl-4,5,9,10-tetrahydropyrene was prepared by the following procedures using 4,5,9,10-tetrahydropyrene as the starting materials. To a solution of 4,5,9,10-tetrahydropyrene (2.065 g, 10 mmol) in CS2 (50 mL) was added anhydrous AlCl3 (3.000 g, 22.6 mmol) at 0 °C under nitrogen atmosphere. Then, acetyl chloride (0.942 g, 12 mmol) in CS2 (20 mL) was added into the mixture. The resulting solution was allowed to warm to room temperature with stirring for 2 h. The reaction mixture was poured into a large amount of 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-acetyl-4,5,9,10-tetrahydropyrene in 87% yield. 1H NMR (400 MHz, CDCl3) δ 7.71 (s, 2H), 7.25–7.18 (m, 1H), 7.14 (d, J = 7.4 Hz, 2H), 3.03–2.89 (m, 8H), 2.64 (m, 3H). GC/MS MS: (C17H14O) m/z 248(M+, 78), 233(100), 202(40), 189(38), 101(20).

The title compound was synthesized by dehydrogenation of the above intermediate 2-acetyl-4,5,9,10-tetrahydropyrene as following: a solution of 2-acetyl-4,5,9,10-tetrahydropyrene (1.220 g, 5 mmol) and DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone; 2.456 g, 10.8 mmol) in 30 mL of freshly-dried benzene was refluxed for 24 h. After removing the solvent by rotary evaporation, the residue was purified by silica gel chromatography using hexane/CH2Cl2 as an eluent to afford 0.8295 g 2-acetyl pyrene in 70% yield. 1H NMR (400 MHz, CDCl3) δ 8.75 (s, 2H), 8.23 (d, J = 7.6 Hz, 2H), 8.18–8.11 (m, 4H), 8.09 (t, J = 7.6 Hz, 1H), 2.93 (s, 3H). GC—MS MS: (C18H12O) m/z 230(M+, 100), 201(95), 100(35). The yellow block crystals of the title compound were obtained by slow evaporation of methanol/CH2Cl2 solution (v:v = 1/10).

Experimental details

All H atoms bond to C atoms were introduced using the HFIX commond in the SHELXL program [2], with the values of 0.93 Å or 0.96 Å for C—H bonds distances, respectively. All H atoms were allowed for as riding atoms with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(C) for hydrogen atoms, respectively. The structure was checked using PLATON [3].

Discussion

Pyrene derivatives have attracted significant attention due to their excellent fluorescence properties, such as high fluorescence quantum yield, outstanding thermal stability, long fluorescence lifetime [4], [5], [6], [7]. Many interesting pyrene-based functional materials have been reported to be used as important organic semiconductors for the applications in organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and organic photovoltaic devices (OPVs) [8], [9], [10], [11]. However, the derivatization of pyrene almost focus on 1-position, or 1-, 3-, 6-, and 8-positions [12], [13], [14], [15]. There are few reports concerning 2-substituted pyrene derivatives due to its hard synthesis [16], [17], [18]. That is because the presence of the nodal plane in the HOMO and LUMO locates perpendicular to the molecule and passes through the 2-position. Herein, we report the synthesis and crystal structure of a compound which involves substitution at the 2-position of the pyrene core.

The single X-ray diffraction analysis agrees well with expected structure of the title compound 2-acetyl pyrene C18H12O. There are two independent 2-acetyl pyrene molecules in the asymmetric unit of the title crystal structure. The acetyl functional group is located at the 2-position of pyrene. The C—O bond lengths are 1.2229(15) Å and 1.2200(14) Å, respectively in the two independent 2-acetyl pyrene molecules, which is the typical double bond distance of an acetyl group. The C1—C3 and C19—C21 bond lengths are 1.4931(17) Å and 1.4937(17) Å, respectively, which are slightly smaller than those C1—C2 and C19—C20 bond lengths, indicating the π–π conjugation effect between pyrenyl moiety and the carbonyl group. All the carbon and oxygen atoms are nearly in a strict plane with the largest deviation 0.116(2) Å and 0.048(2) Å from the mean plane based on all the atoms for the two independent 2-acetyl pyrene molecules, respectively. The dihedral angle of the mean planes based on two 2-acetyl pyrene molecules is 80.65(12)°. Bond lengths and angles are all in the expected ranges and similar to those in the parent structure [19]. There are relatively strong intermolecular π–π interactions between adjacent molecules with the shortest interatomic distance is 3.349(2) Å for two 2-acetyl pyrene molecules in which C1—O1 bond is located, and 3.349(2) Å for another two 2-acetyl pyrene molecules in which C19—O2 bond is located, forming two different dimeric structures [20]. 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 funding research projects of Jiangsu Province 333 high-level talents (BRA2016459).

References

1. Bruker. APEX3, SAINT-Plus, XPREP. Bruker AXS Inc., Madison, WI, USA (2016).Search in Google Scholar

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

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

4. Stylianou, K. C.; Heck, R.; Chong, S. Y.; Bacsa, J.; Jones, J. T. A.; Wong, K. S.; Khimyak, Y. Z.; Bradshaw, D.; Rosseinsky, M. J.: A guest-responsive fluorescent 3D microporous metal-organic framework derived from a long-lifetime pyrene core. J. Am. Chem. Soc. 132 (2010) 4419–4130.10.1021/ja906041fSearch in Google Scholar PubMed

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

6. Sasabe, H.; Kido, J.: Multifunctional materials in high-performance OLEDs: challenges for solid-state lighting. Chem. Mater. 23 (2010) 621–630.10.1021/cm1024052Search in Google Scholar

7. Gingras, M.; Placide, V.; Raimundo, J. M.; Bergamini, G.; Ceroni, P.; Balzani, V.: Polysulfurated pyrene-cored dendrimers: luminescent and electrochromic properties. Chem. Eur. J. 14 (2008) 10357–10363.10.1002/chem.200801198Search in Google Scholar PubMed

8. Huang, J.; Tang, R.; Zhang, T.; Li, Q.; Yu, G.; Xie, S.; Liu, Y.; Ye, S.; Qin, J.; Li, Z.: A new approach to prepare efficient blue AIE emitters for undoped OLEDs. Chemistry 20 (2014) 5317–5326.10.1002/chem.201303522Search in Google Scholar PubMed

9. Chercka, D.; Yoo, S. J.; Baumgarten, M.; Kim, J. J.; Müllen, K.: Pyrene based materials for exceptionally deep blue OLEDs. J. Mater. Chem. C. 2 (2014) 9083–9086.10.1039/C4TC01801JSearch in Google Scholar

10. Liu, Y.; Shan, T.; Yao, L.; Bai, Q.; Guo, Y.; Li, J.; Han, X.; Li, W.; Wang, Z.; Yang, B.; Lu, P.; Ma, Y.: Isomers of pyrene-imidazole compounds: synthesis and configuration effect on optical properties. Org. Lett. 17 (2015) 6138–6141.10.1021/acs.orglett.5b02879Search in Google Scholar PubMed

11. Niko, Y.; Sasaki, S.; Narushima, K.; Sharma, D. K.; Vacha, M.; Konishi, G.: 1-, 3-, 6-, and 8-Tetrasubstituted asymmetric pyrene derivatives with electron donors and acceptors: high photostability and regioisomer-specific photophysical properties. J. Org. Chem. 80 (2015) 10794–10805.10.1021/acs.joc.5b01987Search in Google Scholar PubMed

12. 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 Pigm. 130 (2016) 106–115.10.1016/j.dyepig.2016.03.020Search in Google Scholar

13. Zhang, R.; Zhang, T. F.; Xu, L.; Han, F. F.; Zhao, Y.; Ni, Z. H.: A new series of short axially symmetrically and asymmetrically 1,3,6,8-tetrasubtituted pyrenes with two types of substituents: syntheses, structures, photophysical properties and electroluminescence. J. Mol. Struct. 1127 (2017) 237–246.10.1016/j.molstruc.2016.07.105Search in Google Scholar

14. Hu, J. Y.; Feng, X.; Tomiyasu, H.; Seto, N.; Rayhan, U.; Elsegood, M. R. J.; Redshaw, C.; Yamato, T.: Synthesis and fluorescence emission properties of 1,3,6,8-tetraarylpyrenes. J. Mol. Struct. 1047 (2013) 194–203.10.1016/j.molstruc.2013.04.074Search in Google Scholar

15. Zhang, R.; Han, F. F.; Zhang, L. F.: Crystal structure of 2-(4-methylbenzoyl)pyrene, C24H16O. Z. Kristallogr. NCS 231 (2016) 855–857.10.1515/ncrs-2015-0292Search in Google Scholar

16. Laali, K. K.; Arrica, M. A.; Okazaki, T.; Bunge, S. D.: Synthesis and stable-ion studies of regioisomeric acetylnitropyrenes and nitropyrenyl carbinols and giao-dft study of nitro substituent effects on α-pyrenyl carbocations. Eur. J. Org. Chem. 36 (2008) 6093–6105.10.1002/ejoc.200800849Search in Google Scholar

17. Cabral, L. I. L.; Henriques, M. S. C.; Paixão, J. A.; Cristiano, M. L. S.: Synthesis and structure of 2-substituted pyrene-derived scaffolds. Tetra. Lett. 58 (2017) 4547–4550.10.1016/j.tetlet.2017.10.058Search in Google Scholar

18. Suzuki, S.; Takeda, T.; Kuratsu, M.; Kozaki, M.; Sato, K.; Shiomi, D.; Takui, T.; Okada, K.: Pyrene-dihydrophenazine bis(radical cation) in a singlet ground state. Org. Lett. 11 (2009) 2816–2818.10.1021/ol9009927Search in Google Scholar PubMed

19. Bao-Xi, M.; Xin-Xue, T.; Li-Fang, Z.: Crystal structure of pyrene-2-carbaldehyde, C17H10O. Z. Kristallogr. NCS 233 (2018) 655–657.10.1515/ncrs-2017-0423Search in Google Scholar

20. Martinez, C. R.; Iverson, B. L.: Rethinking the term “p-stacking”. Chem. Sci. 3 (2012) 2191–2201.10.1039/c2sc20045gSearch in Google Scholar

Received: 2018-10-15
Accepted: 2018-11-06
Published Online: 2018-12-05
Published in Print: 2019-03-26

©2019 Yun-Hui Xu 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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  47. Crystal structure of dichlorido bis[1-((2,4-dimethyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN]cadmium(II), Cd(C12H13N5)2Cl2
  48. The crystal structure of 1,5-di(naphthalen-2-yl)-3-(pyridin-2-yl)pentane-1,5-dione, C30H23NO2
  49. The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
  50. The crystal structure of 1,4-dinitroso-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O10
  51. Crystal structure of bis(2,4,6-trichlorophenyl) malonate, C15H6Cl6O4
  52. The crystal structure of trans-dichlorido-bis(pyridine-2-carboxylato-κ2N,O)platinum(IV), C12H8Cl2N2O4Pt
  53. Crystal structure of 3-nitroquinoline 1-oxide, C9H6N2O3
  54. Crystal structure of 2-(piperidin-1-ium-4-yl)-1H-benzo[d]imidazol-3-ium dichloride dihydrate, C12H21Cl2N3O2
  55. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene, C30H50O
  56. Crystal structure of (E)-4-((2-fluoro-3-(trifluoromethyl)benzylidene)amino)-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C11H8F4N4S
  57. Crystal structure of 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C9H8FN3S
  58. Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
  59. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C9H8O4
  60. The crystal structure of N,N′-(6-(thiophen-2-yl)-1,3,5-triazine-2,4-diyl)bis(2-methylpropane-2-sulfonamide) – ethyl acetate(2/1), C34H54N10O6S6
  61. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2
  62. Crystal structure of 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one, C16H12O2
  63. Crystal structure of N′-(1-(benzofuran-2-yl)ethylidene)-2-cyanoacetohydrazide, C13H11N3O2
  64. Crystal structure of hexa-μ2-chlorido-μ4-oxido-tetrakis(1-vinyl-1H-imidazole-κN)tetracopper(II), C20H24Cu4Cl6N8O
  65. Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S
  66. Crystal structure of 2-acetyl pyrene, C18H12O
https://doi.org/10.1515/ncrs-2018-0432
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Articles in the same Issue

  1. Cover and Frontmatter
  2. Crystal structure of 1H-indole-5-carboxylic acid – 4,4′-bipyridine (2/1), C14H11N2O2
  3. Crystal structure of ethyl 2-amino-4-(4-ethoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c] chromene-3-carboxylate, C23H21NO6
  4. Crystal structure of ethyl 2-amino-4-(4-bromothiophen-2-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate, C16H16BrNO4S
  5. The crystal structure of 6-amino-2-methyl-8-(4-(methylthio)phenyl)-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile – ethanol (1/1), C20H19N5S
  6. Crystal structure of 6-amino-8-(4-isopropylphenyl)-2-methyl-2,3,8,8a-tetrahydroisoquinoline-5,7,7(1H)-tricarbonitrile-ethanol (1/1), C24H29N5O
  7. Crystal structure of 1,1′-(ethane-1,2-diyl)bis(3-ethyl-1H-imidazol-3-ium)bis(hexafluorido phosphate), C12H20F12N4P2
  8. Crystal structure of dimethyl (3aS,6R,6aS,7S)-2-pivaloyl-2,3-dihydro-1H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isoquinoline-3a1,6a-dicarboxylate, C21H25NO8
  9. Crystal structure of methyl 4-(4-bromothiophen-2-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H20BrNO3S
  10. Hydrothermal synthesis and crystal structure of catena-poly[bis(4-((pyridin-4-ylmethyl)amino)benzoato-κ3N:O,O′)zinc(II) – 1,2-di(pyridin-4-yl)ethene – water (1/1/1), C38H34N6O5Zn
  11. The crystal structure of 1,2-dimethyl-3,4-dinitrobenzene, C8H8N2O4
  12. Synthesis and crystal structure of trans-tetraaqua-bis(3-(((7-hydroxy-3-(4-hydroxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)ammonio)propanoato-κO)zinc(II) tetrahydrate, C38H48N2O26S2Zn
  13. Crystal structure of diaqua-bis(μ2-6-chloropyridin-2-olato-κ3N,O:O)-tetrakis(chloropyridin-2-olato-κ1O)-bis(penanthroline-κ2N,N′)diterbium(III), C54H38Cl6Tb2N10O8
  14. Crystal structure of oxidobis(piperidine-1-carbodithioato-κ2S,S′)vanadium(IV), C12H20N2OS4V
  15. Crystal structure of 2-((tert-butyldimethylsilyl)oxy)-5-methylisophthalaldehyde, C15H22O3Si
  16. Crystal structure of catena-poly[tetraiodido-(μ2-1,4-bis(2-methyl-1H-imidazol-1-yl)benzene-κ2N:N′)dimercury(II)], C14H14Hg2I4N4
  17. Crystal structure of tetrakis(n-butyl)-(μ2-1,2-bis(2-oxidobenzoyl)hydrazine-1,2-diido-κ6N,O,O′:N′,O′′,O′′′)ditin(IV), C30H44N2O4Sn2
  18. Crystal structure of ethyl 2-amino-4-(4-hydroxy-3-methoxyphenyl)-7-methyl-5-oxo-4H,5H-pyrano-[4,3-b]pyran-3-carboxylate, C19H19NO7
  19. Crystal structure of 3-aminopyrazine-2-carbohydrazide, C5H7N5O
  20. Crystal structure of ethanol-bis(N-((5-(ethoxycarbonyl)-3,4-dimethyl-1H-pyrrol-2-yl)methylene)benzohydrazonato-κ2N,O)copper(II), C36H42N6O7Cu
  21. Crystal structure of 3-methyl-2-oxo-2H-chromen-7-yl propionate, C13H12O4
  22. Crystal structure of 2-(dimethylamino)ethyl 4-aminobenzoate, C11H16N2O2
  23. Crystal structure of 3-(benzo[d]thiazol-2-ylamino)isobenzofuran-1(3H)-one, C15H10N2O2S
  24. Crystal structure of 3-((1H-benzo[d]imidazol-2-yl)amino)-2-(1H-benzo[d]imidazol-2-yl)isoindolin-1-one, C22H16N6O
  25. Crystal structure of (2,2′-bipyridine-κ2N,N′)bis(4-(dimethylamino)phenyldiphenylphosphane-κP)copper(I) tetrafluoroborate, C50H48BCuF4N4P2
  26. Crystal structure of citric acid–acetonitrile (1/1), C8H11NO7
  27. Crystal structure of diethyl 2-(4-methoxyphenyl)-1-phenyl-1,2-dihydropyridine-3,5-dicarboxylate, C24H25NO5
  28. The crystal structure of poly[triaqua-bis(μ3-2,5-dihydroxyterephthalato-κ4O,O′:O′′:O′′′)-(μ4-oxalato-κ4O,O′:O′′,O′′′)cerium(III)], C9H10CeO11
  29. Crystal structure of 1-(5-(anthracen-9-yl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)propan-1-one, C26H22N2O2
  30. Synthesis and crystal structure of 5-(8-(((2-carboxyethyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate trihydrate, C19H23NO12S
  31. Crystal structure of rac-trans-6,6′-((cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene))bis(2-bromophenolato-κ4N,N′,O,O′)-bis(methanol)cobalt(III) chloride, C22H25Br2Co8N2O4Cl
  32. Crystal structure of 1-((R)-(2′-(dimethylamino)-[1,1′-binaphthalen]-2-yl))-3-((S)-2-hydroxy-1-phenylethyl)thiourea, C31H29N3OS
  33. Crystal structure and photochemical property of 1,8-bis(p-tolylthio)pyrene, C30H22S2
  34. Crystal structure of 2-(2-(2-amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate, C14H18ClN5O4
  35. Crystal structure of ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate, C11H12N4O2
  36. Crystal structure of trichloro-(4-chloro-2,6-bis(diphenylmethyl)-N-((pyridin-2-yl)methylene)aniline)-aluminum dichloromethane solvate, C39H31AlCl6N2
  37. Bis(ethanol-κO)-bis(6-aminopicolinato-κ2N,O)magnesium(II), C16H22O6N4Mg
  38. Crystal structure of catena-poly[aqua-(μ2-1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ2O:O′)-(1,10-phenanthrolin-κ2N,N′)copper(II)], C16H20B10CuN2O5
  39. Crystal structure of (1,2-dicarba-closo-dodecaborane-1,2-dithiolato κ2S,S′)-bis(1,10-phenanthroline κ2N,N′)zinc(II), C26H26B10Zn4S2
  40. Crystal structure of diaqua-bis(1,10-phenanthroline-κ2N,N′)-bis(1,7-dicarba-closo-dodecaborane-1,7-dicarboxylato-κ3O,O′:O′′) dicobalt(II) — ethanol (1/1), C34H46B20Co2N4O11
  41. Crystal structure of ((5,5′-dimethoxy-2,2′-(1,2-phenylenebis(nitrilomethylidyne)))diphenolato-κ4O,N,O′,N′)copper(II), C22H18N2CuO4
  42. Crystal structure of 1-(5-bromo-2-(4-methoxyphenyl)-1H-indol-7-yl)ethan-1-ol, C17H14BrNO2
  43. Crystal structure of (E)-2-(((6-bromopyridin-2-yl)methylene)amino)-3′,6′-bis(diethylamino)spiro[isoindoline-1,9′-xanthen]-3-one, C34H34N5O2Br
  44. Crystal structure of (Z)-2-((adamantan-1-ylimino)methyl)-5-methoxyphenol, C18H23NO2
  45. Crystal structure of bis((E)-2-ethoxy-6-(((2-hydroxyethyl)imino)methyl)phenolato-κ2N,O)copper(II), C22H28N2CuO6
  46. Crystal structure of 2,3-diphenyl-5,6-bis(4-methoxyphenyl)pyrazine, C30H24N2O2
  47. Crystal structure of dichlorido bis[1-((2,4-dimethyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN]cadmium(II), Cd(C12H13N5)2Cl2
  48. The crystal structure of 1,5-di(naphthalen-2-yl)-3-(pyridin-2-yl)pentane-1,5-dione, C30H23NO2
  49. The crystal structure of 2-((3-methylthiophen-2-yl)methylene)malononitrile, C9H6N2S
  50. The crystal structure of 1,4-dinitroso-2,3,5,6-tetraacetoxy-piperazine, C12H16N4O10
  51. Crystal structure of bis(2,4,6-trichlorophenyl) malonate, C15H6Cl6O4
  52. The crystal structure of trans-dichlorido-bis(pyridine-2-carboxylato-κ2N,O)platinum(IV), C12H8Cl2N2O4Pt
  53. Crystal structure of 3-nitroquinoline 1-oxide, C9H6N2O3
  54. Crystal structure of 2-(piperidin-1-ium-4-yl)-1H-benzo[d]imidazol-3-ium dichloride dihydrate, C12H21Cl2N3O2
  55. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene, C30H50O
  56. Crystal structure of (E)-4-((2-fluoro-3-(trifluoromethyl)benzylidene)amino)-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C11H8F4N4S
  57. Crystal structure of 5-(4-fluorophenyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione, C9H8FN3S
  58. Crystal structure of catena-poly[(1-(4-fluorophenyl)-N–(5-((trimethylstannyl)thio)-1,3,4-thiadiazol-2-yl)methanimine], (C12H14FN3S2Sn)n
  59. The crystal structure of 4-(methoxycarbonyl)benzoic acid, C9H8O4
  60. The crystal structure of N,N′-(6-(thiophen-2-yl)-1,3,5-triazine-2,4-diyl)bis(2-methylpropane-2-sulfonamide) – ethyl acetate(2/1), C34H54N10O6S6
  61. Crystal structure of N′-(1-(2-hydroxyphenyl)ethylidene)-5-methyl-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide, C18H17N5O2
  62. Crystal structure of 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one, C16H12O2
  63. Crystal structure of N′-(1-(benzofuran-2-yl)ethylidene)-2-cyanoacetohydrazide, C13H11N3O2
  64. Crystal structure of hexa-μ2-chlorido-μ4-oxido-tetrakis(1-vinyl-1H-imidazole-κN)tetracopper(II), C20H24Cu4Cl6N8O
  65. Crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-4-methylbenzenesulfonohydrazide, C22H22O5N2S
  66. Crystal structure of 2-acetyl pyrene, C18H12O
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