Startseite Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
Artikel Open Access

Crystal structure of 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O

  • Yang Jien EMAIL logo und Chen Songhua
Veröffentlicht/Copyright: 15. Oktober 2018

Abstract

C22H20N2O, monoclinic, P21/n (no. 14), a = 8.316(2) Å, b = 9.247(2) Å, c = 20.908(5) Å, β = 93.538(5)°, V = 1604.7(7) Å3, Z = 4, Rgt(F) = 0.0618, wRref(F2) = 0.1527, T = 173(2) K.

CCDC no.: 1832467

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:Rod, yellow
Size:0.27 × 0.27 × 0.16 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.08 mm−1
Diffractometer, scan mode:Saturn724+, ω-scans at fixed χ = 45°
θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:9902, 2816, 0.043
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2624
N(param)refined:229
Programs:Rigaku program [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.27602(19)0.18905(18)0.05131(8)0.0458(5)
N10.6039(2)0.51239(18)0.09521(8)0.0289(4)
N2−0.3893(2)0.4571(2)0.33768(9)0.0368(5)
C10.5296(2)0.2943(2)0.03534(10)0.0284(5)
C20.5679(3)0.1896(2)−0.00961(10)0.0331(5)
H20.4916420.116170−0.0211110.040*
C30.7129(3)0.1905(2)−0.03744(12)0.0397(6)
H30.7370200.119072−0.0680820.048*
C40.8239(3)0.2981(3)−0.01990(12)0.0433(6)
H40.9256410.297997−0.0381930.052*
C50.7903(3)0.4045(2)0.02316(11)0.0369(5)
H50.8678420.4775600.0336710.044*
C60.6408(2)0.4056(2)0.05188(10)0.0284(5)
C70.4642(2)0.5036(2)0.12823(9)0.0266(5)
C80.3517(2)0.3921(2)0.11535(10)0.0264(5)
C90.3768(2)0.2843(2)0.06611(10)0.0300(5)
C100.4302(2)0.6051(2)0.17607(10)0.0307(5)
H100.5031180.6823430.1856100.037*
C110.2930(2)0.5932(2)0.20888(10)0.0306(5)
H110.2731000.6636910.2405070.037*
C120.1803(2)0.4810(2)0.19766(10)0.0271(5)
C130.2131(2)0.3831(2)0.15025(10)0.0279(5)
H130.1390080.3067370.1408980.033*
C140.0358(2)0.4683(2)0.23560(10)0.0272(5)
C150.0275(2)0.5330(2)0.29572(10)0.0314(5)
H150.1192730.5831310.3136300.038*
C16−0.1090(3)0.5271(2)0.33017(10)0.0318(5)
H16−0.1084550.5719240.3710580.038*
C17−0.2490(2)0.4553(2)0.30546(10)0.0295(5)
C18−0.2384(2)0.3827(2)0.24710(11)0.0319(5)
H18−0.3275280.3273410.2303340.038*
C19−0.1005(2)0.3901(2)0.21332(10)0.0299(5)
H19−0.0983770.3402660.1736420.036*
C200.7136(3)0.6347(2)0.10633(12)0.0378(6)
H20B0.6533220.7182280.1210030.057*
H20A0.7629150.6592880.0663670.057*
H20C0.7979970.6086390.1390810.057*
C21−0.5216(3)0.3618(3)0.31858(11)0.0382(6)
H21A−0.5391460.3628290.2717970.057*
H21C−0.6195010.3947670.3379530.057*
H21B−0.4958370.2632070.3330400.057*
C22−0.3912(3)0.5206(3)0.40119(11)0.0406(6)
H22A−0.3308940.4584930.4321660.061*
H22C−0.5027640.5295500.4132530.061*
H22B−0.3411680.6165380.4009920.061*

Source of materials

The title compound was obtained by C—C bond formation of 2-bromo-10-methylacridin-9(10H)-one and (4-(dimethylamino)phenyl)boronic acid via a Suzuki coupling reaction with equal ratio in toluene under the catalysis of Pd(PPh3)4. The compound was further purified through flash column chromatography with dichloromethane as eluent. Single crystals were obtained by crystallization from methanol and dichloromethane.

Experimental details

The hydrogen atoms were placed with common isotropic displacement factors Uiso(H) = 1.2 times Ueq (C, aromatic ring), and Uiso(H) = 1.5 times Ueq (C, methyl). The final refinement succeeded using geometrical restraints, with C—H = 0.95 Å (aromatic ring), and C—H = 0.98 Å (methyl).

Comment

The organic small molecules with tuning optical nonlinear properties have attracted considerable academic and technological research at tention [4], [5], [6], [7]. Those molecules usually have a donor-acceptor (D—A) structure and the properties could be tuned through matching the suitable units. Acridone derivatives with electron-deficient properties are acceptor candidates in the constructing D—A molecules [8], [9]. Meanwhile, the N,N-dimethylaniline plays the role of donor units [10] and the two parts are connected by a C–C single bond of 1.485(3) Å, which is shorter than that in 2-bromo-7-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, because of the electron-withdrawing property of bromine atom. This molecules was expected to be applied in the optical tuning field. The asymmetric unit contains one molecule of the title compound with a dihedral angle of −21.6(3)° between the two planes of the acridonyl [11] and the aryl moiety.

Acknowledgements

This work was funded by National Nature Science Foundation of China (no. 21402042). Doctoral Science Foundation of Henan Normal University (no. 01026500259) and the research funds of Longyan University.

References

1. Rigaku: CrystalClear. Rigaku Corporation, Tokyo, Japan (2007).Suche in Google Scholar

2. Sheldrick, G. M.: SHELXS97. Program for the Solution of Crystal Structures. University of Göttingen, Germany (1997).Suche in Google Scholar

3. Sheldrick, G. M.: Crystal structure refinement with SHELX. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

4. Albota, M.; Beljonne, D.; Brédas, J.-L.; Ehrlich, J. E.; Fu, J.-Y.; Heikal, A. A.; Hess, S. E.; Kogej, T.; Levin, M. D.; Marder, S. R.: Design of organic molecules with large two-photon absorption cross sections. Science. 281 (1998) 1653–1656.10.1126/science.281.5383.1653Suche in Google Scholar PubMed

5. Staub, K.; Levina, G. A.; Barlow, S.; Kowalczyk, T. C.; Lackritz, H. S.; Barzoukas, M.; Fort, A.; Marder, S. R.: Synthesis and stability studies of conformationally locked 4-(diarylamino) aryl-and 4-(dialkylamino) phenyl-substituted second-order nonlinear optical polyene chromophores. J. Mater. Chem. 13 (2003) 825–833.10.1039/b208024aSuche in Google Scholar

6. Barlow, S.; Marder, S. R.: “Nonlinear optical properties of organic materials,” in Functional Organic Materials: Syntheses, Strategies and Applications, Müller, T. J. J.; Bunz, U. H. F.: Eds., Chapter 11, 393–437, Wiley-VCH, Weinheim, Germany, 2006.10.1002/9783527610266.ch11Suche in Google Scholar

7. Raghavendra, S.; Kumar, C. C.; Shetty, T. C. S.; Lakshminarayana, B.; Quah, C. K.; Chandraju, S.; Ananthnag, G.; Gonsalves, R.; Dharmaprakash, S.: Structure property relationship of a new nonlinear optical organic crystal: 1-(3,4-dimethoxyphenyl)-3-(3-fluorophenyl)prop-2-en-1-one for optical power limiting applications. Results in Physics. 7 (2017) 2550–2556.10.1016/j.rinp.2017.07.037Suche in Google Scholar

8. Sharma, B. K.; Shaikh, A. M.; Agarwal, N.; Kamble, R. M.: Synthesis, photophysical and electrochemical studies of acridone-amine based donor-acceptors for hole transport materials. RSC Adv. 6 (2016) 17129–17137.10.1039/C5RA25115JSuche in Google Scholar

9. Hemgesberg, M.; Ohlmann, D. M.; Schmitt, Y.; Wolfe, M. R.; Müller, M. K.; Erb, B.; Sun, Y.; Gooßen, L. J.; Gerhards, M.; Thiel, W. R.: Simple access to sol–gel precursors bearing fluorescent aromatic core units. Eur. J. Org. Chem. 2012 (2012) 2142–2151.10.1002/ejoc.201200076Suche in Google Scholar

10. Chen, S.; Li, Y.; Yang, W.; Chen, N.; Liu, H.; Li, Y.: Synthesis and Tuning optical nonlinear properties of molecular crystals of benzothiadiazole. J. Phys. Chem. C. 114 (2010) 15109–15115.10.1021/jp103159bSuche in Google Scholar

11. Takeda, T.; Akutagawa, T.: Anisotropic dissociation of π–π stacking and flipping-motion-induced crystal jumping in alkylacridones and their dicyanomethylene derivatives. Chem. – Eur. J. 22 (2016) 7763–7770.10.1002/chem.201600794Suche in Google Scholar PubMed

Received: 2018-08-16
Accepted: 2018-10-07
Published Online: 2018-10-15
Published in Print: 2018-12-19

©2018 Yang Jien et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

Artikel in diesem Heft

  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
Heruntergeladen am 22.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2018-0310/html
Button zum nach oben scrollen