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Crystal structure of 1,1-di(4-cyanophenyl)-2,2-diphenylethene, C28H18N2

  • Miao Bao-Xi , Sun Hao and Ni Zhong-Hai EMAIL logo
Published/Copyright: May 22, 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

C28H18N2, orthorhombic, Pccn (no. 56), a = 9.8955(6) Å, b = 11.0163(6) Å, c = 19.9752(14) Å, V = 2177.5(2) Å3, Z = 4, Rgt(F) = 0.0402, wRref(F2) = 0.1012, T = 123(2) K.

CCDC no.: 1840632

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:

Crystal collection and handling.

Crystal:block, yellow
size:0.16 × 0.10 × 0.06 mm
Wavelength:Mo K αradiation (λ = 0.71073 Å)
μ:0.068 mm−1
Diffractometer, scan mode:Bruker APEX II, Φ and ω-scans
θmax, completeness:26.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:20003, 2229, 0.0446
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 1949
N(param)refined:137
Programs:Bruker programs [1], SHELX [2], PLATON [3]
Table 2:

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

AtomxyzUiso*/Ueq
N10.55161(13)0.76255(11)0.50231(6)0.0376(3)
C10.57888(14)0.67316(12)0.47676(7)0.0274(3)
C20.61666(13)0.56147(11)0.44331(6)0.0228(3)
C30.73620(13)0.50308(11)0.46132(6)0.0249(3)
H30.78880.53320.49620.030
C40.77618(12)0.39994(11)0.42703(6)0.0224(3)
H40.85480.35980.43980.027
C50.69997(12)0.35547(10)0.37361(6)0.0189(3)
C60.57695(12)0.41189(11)0.35840(6)0.0216(3)
H60.52270.38020.32460.026
C70.53510(12)0.51390(11)0.39279(6)0.0234(3)
H70.45310.55060.38230.028
C80.75000.25000.33368(8)0.0191(3)
C90.75000.25000.26570(9)0.0206(4)
C100.78197(13)0.13901(11)0.22566(6)0.0224(3)
C110.72256(13)0.02739(11)0.24041(7)0.0260(3)
H110.65980.02180.27490.031
C120.75656(15)−0.07574(12)0.20389(7)0.0333(3)
H120.7172−0.14990.21460.040
C130.84816(16)−0.06912(13)0.15191(8)0.0377(4)
H130.8714−0.13860.12810.045
C140.90509(17)0.04175(14)0.13558(7)0.0380(4)
H140.96560.04710.10010.046
C150.87219(15)0.14520(13)0.17196(7)0.0303(3)
H150.91070.21930.16040.036

Source of materials

1,1-Di(4-bromophenyl)-2,2-diphenylethene was synthesized according to the literature [4]. All other chemicals were purchased and used as received. A mixture of 1,1-di(4-bromophenyl)-2,2-diphenylethene (1.471 g, 3 mmol) and CuCN (0.717 g, 8 mmol) in dry DMF (45 mL) was heated at reflux under nitrogen for three days. A mixture of ethylenediamine (10 mL) and water (15 mL) was added after the mixture had cooled to 90 °C. The resulting mixture was stirred at 90 °C for 3 h and then cooled to room temperature. The product was extracted with dichloromethane three times and the organic layer dried over magnesium sulfate, filtered, and evaporated. A quantity of 0.802 g (70% yield) of C28H18N2 was isolated as yellow crystals. 1H NMR (600 MHz, DMSO-d6) δ 7.71 (d, J = 8.1 Hz, 2H), 7.16 (t, J = 7.9 Hz, 3H), 7.08 (d, J = 8.0 Hz, 2H), 7.04⋯6.96 (m, 2H). MALDI-TOF MS: m/z calculated for C28H18N2 382.4560, found 382.4321 [M]+. Elemental analysis calculated for C28H18N2 : C, 87.93; H, 4.74; N, 7.33%; found: C, 87.80, H, 4.63; N, 7.27%.

Yellow block crystals were obtained by slow evaporation of methanol/methylene dichloride solution.

Experimental details

All H atoms bond to C atoms were introduced using the HFIX command in the SHELXL program [2]. All H atoms were treated as riding atoms with Uiso(H) = 1.2 Ueq(C) for hydrogen atoms. The structure was checked using PLATON [3]. There is a void in the unit cell, which has a volume of 32 Å3.

Comment

Aggregation-induced emission (AIE) phenomenon of fluorescent solid materials have attracted significant attention because of their wide applications such as organic light-emitting diodes (OLEDs), solar cells, bioimaging, optoelectronic, optomechanical switching and storage devices [5], [6], [7], [8], [9], [10]. As an iconic AIE molecule, tetraphenylethylene (TPE) and derivatives have been used to develop new fluorescent materials, such as highly solid fluorescence quantum yield owing to their rich electrochemical and excited state properties [11], [12], [13]. It is well known that the electronic structures and optoelectronic properties of TPE can be facilely modulated through tuning the electron donor and acceptor groups. Amongst various strong electron acceptor groups, the cyano group is the special one: solid fluorescence quantum yield of TPE derivatives with cyano group has increased rather than decreased. TPE derivatives with cyano groups show special characteristic such as highly solid fluorescence quantum yield, intriguing TADF properties, multicolor mechanochromism, and so on [14], [15], [16]. Up to now, a few TPE derivatives directly connected cyano group were obtained because of its symmetrical structure and active positions [17].

The crystal structure analysis agrees with expected structure of the title compound. The molecular structure has almost axial symmetry. The cyano groups are at the expected sites. The C—N bond length is 1.1414(18) Å, which is the typical bond distance. The molecular structure displays twisted paddle-like conformation. As expected, there are no intermolecular π–π interactions. However, there exist weak intermolecular C—H⋯π and C—H⋯N interactions. C—H⋯N interactions link molecules into a ladder-like one-dimensional structure. These are linked by C—H⋯π interactions, giving a three-dimensional structure.

Acknowledgements

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

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Received: 2018-03-13
Accepted: 2018-04-30
Published Online: 2018-05-22
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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  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-2018-0076
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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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