Home Crystal structure of 4′-amino-3′,5′-diisopropyl-(1,1′-biphenyl)-4-carbonitrile, C19H22N2
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Crystal structure of 4′-amino-3′,5′-diisopropyl-(1,1′-biphenyl)-4-carbonitrile, C19H22N2

  • Shuang-Ming Mo and Da-Bin Shi ORCID logo EMAIL logo
Published/Copyright: April 16, 2020

Abstract

C19H22N2, triclinic, P1̄ (no. 2), a = 8.1330(5) Å, b = 9.3474(5) Å, c = 12.1520(8) Å, α = 87.278(5)°, β = 71.092(6)°, γ = 66.190(6)°, V = 795.88(9) Å3, Z = 2, Rgt(F) = 0.0498, wRref(F2) = 0.1415, T = 293(2) K.

CCDC no.: 1971170

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:Colourless block
Size:0.20 × 0.20 × 0.20 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:0.52 mm−1
Diffractometer, scan mode:SuperNova, φ and ω
θmax, completeness:73.5°, 99%
N(hkl)measured, N(hkl)unique, Rint:4642, 3041, 0.026
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2743
N(param)refined:195
Programs:CrysAlisPRO [1], SHELX [2], [3]
Table 2:

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

AtomxyzUiso*/Ueq
C11.36460(18)−0.09322(15)0.10047(11)0.0297(3)
C21.27955(17)−0.00035(15)0.21130(10)0.0258(3)
C31.29136(18)−0.07450(14)0.31218(11)0.0274(3)
H31.359314−0.1826830.3073590.033*
C41.20179(17)0.01314(14)0.41956(10)0.0270(3)
H41.211578−0.0372840.4864710.032*
C51.09649(16)0.17618(13)0.43025(10)0.0231(3)
C61.08856(17)0.24886(14)0.32721(10)0.0252(3)
H61.0214900.3571200.3316410.030*
C71.17870(18)0.16237(14)0.21921(10)0.0269(3)
H71.1721720.2125510.1518280.032*
C80.99380(17)0.26620(13)0.54654(10)0.0232(3)
C91.05474(17)0.21262(13)0.64188(10)0.0243(3)
H91.1654120.1215050.6299840.029*
C100.95688(17)0.28982(14)0.75331(10)0.0244(3)
C110.78960(17)0.42900(14)0.77139(10)0.0246(3)
C120.72247(17)0.48523(13)0.67690(10)0.0234(3)
C130.82646(17)0.40341(13)0.56731(10)0.0234(3)
H130.7834380.4410930.5050850.028*
C141.02937(19)0.22927(15)0.85452(11)0.0292(3)
H140.9178410.2505890.9248250.035*
C151.1394(2)0.31898(18)0.87570(13)0.0414(4)
H15A1.2529910.2965210.8095740.062*
H15B1.1733000.2869220.9444090.062*
H15C1.0608770.4297310.8864070.062*
C161.1522(2)0.05297(17)0.83884(13)0.0407(4)
H16A1.087289−0.0020940.8184070.061*
H16B1.1749050.0196800.9105130.061*
H16C1.2716570.0303700.7777450.061*
C170.53474(17)0.62867(14)0.69937(11)0.0280(3)
H170.5331370.7065640.7513760.034*
C180.5060(2)0.70635(15)0.58957(12)0.0349(3)
H18A0.6152220.7265850.5469190.052*
H18B0.3943110.8035830.6114860.052*
H18C0.4903680.6376870.5413280.052*
C190.36701(19)0.58555(17)0.76319(14)0.0406(4)
H19A0.3554300.5190230.7109770.061*
H19B0.2515290.6795670.7890310.061*
H19C0.3890930.5310890.8294890.061*
N11.42881(18)−0.16902(14)0.01327(10)0.0393(3)
N20.69287(17)0.50982(13)0.88095(9)0.0359(3)
H2A0.7343840.4754830.9379470.043*
H2B0.5909940.5945940.8923350.043*

Source of material

In a flask, 2,6-diisopropyl aniline (9.4 g, 53 mmol) was introduced in 50 mL CH2Cl2/MeOH (1/1). After that, Br2 (8.5 g, 107 mmol) in 50 mL CH2Cl2/MeOH (1/1) was added dropwise over 30 min. The mixture was stirred at 25 °C for 20 h, yielding a dark suspension. After complete consumption of the starting material, the solvent was removed under reduced pressure. The crude product was recrystallized from 1/1 CH2Cl2/hexane (50 mL). The precipitate was filtered and washed with 20 mL of cold hexane. The residue was neutralized with 75 mL (5 mL g−1) of 20 wt% aqueous NaOH solution for 4 h. Upon extraction with diethyl ether for three times, the organic extracts were combined, and dried over sodium sulfate, and filtered. Removal of volatiles under reduced pressure yielded 12.5 g (92%) of 4-bromo-2,6-diisopropylaniline as a yellow oil.

Synthesis of the title compound [4]. A mixture of (4-cyanophenyl)boronic acid (8.1 g, 55 mmol, 1.1 equiv), 4-bromo-2,6-diisopropylaniline (12.8 g, 50 mmol), palladium tetrakis(triphenylphosphine) (1.1 g, 1 mmol, 2 mol%), and potassium carbonate (17.4 g, 165 mmol, 3.3 equiv) in 200 mL dioxane/H2O (3/1) was stirred under nitrogen for 72 h at 90 °C. After the mixture was cooled to room temperature, it was extracted with CH2Cl2 and washed with H2O. The organic layer was dried with MgSO4, and the solvent was removed. The resulting crude product was purified by column chromatography using silica gel and petroleum ether/ethyl acetate (20/1) as the eluent. The product was obtained (10.8 g, 78.0% yield). Crystals were obtained by slow evaporation of an ethanol solution at room temperature over a period of seven days, yield: 0.68 g (92%). M.p.: 182–183 °C. Elemental analysis – found: C, 81.91%; H, 7.92%; N, 10.12%; calculated for C20H25NO2: C, 81.97%; H, 7.97%; N, 10.06%.

Experimental details

Data were collected via CrysAlisPRO [1], the structure of crystal was solved by SHELXT [2] and refined by SHELXL [3].

Comment

Xenylamine derivatives were usually used as ligands to construct organometallic complexes, used in various catalytic reactions [5], [6], [7]. Yuan et al. [8] reported a series of phenyl substituted α-diimine nickel complexes activated by Et2AlCl exhibiting high activities toward ethylene polymerization to afford highly branched polyethylene. Coates et al. reported precision chain-walking polymerization of linear 1-alkenes using the sandwich α-diimine nickel catalysts, which afforded semicrystalline polyethylene [9]. Finally the syntheses, crystal structure, spectroscopic characterization, and physical properties of a class of benzidine radical cations were reported [10]. As part of this project, we have previously reported the synthesis and crystal structure of a diphenylamine [11].

In the crystal structure, the dihedral angle between the planes of two phenyl rings is 27.9° (cf. the figure). Bond lengths and bond angles within the molecule are in agreement with the values reported. The bond lengths of C1—N1 and C11—N2 are 1.1452(17) Å and 1.3781(15) Å, respectively. As a result of the conjugation of the aromatic rings, the bond length of C5—C8 is 1.4776(16) Å, which is shorter than that of typical C—C single bond. There is an intermolecular hydrogen bond (d D⋯A 3.037 Å; H⋯A 2.341 Å) between N2—H2B⋯N1′(′ = x − 1, y + 1, z + 1), which produces a one dimensional chain to stabilize the crystal structure.

Acknowledgements

We are grateful for financial support from National Natural Science Foundation of China (grant no. 21861045).

References

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Received: 2020-01-19
Accepted: 2020-03-10
Published Online: 2020-04-16
Published in Print: 2020-06-25

©2020 Shuang-Ming Mo 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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  72. Crystal structure of bromido-triphenyl-(triphenylarsine oxide-κO)tin(IV), C36H30AsBrOSn
  73. Crystal structure of catena-poly[chlorido-(μ2-formato-κ2O:O′)-(1,10-phenathroline-κ2N,N′)copper(II)], C26H18Cl2Cu2N4O4
  74. The crystal structure of poly[(μ10-5-carboxyisophthalato-κ10O)disodium], C9H4Na2O6
  75. The crystal structure of 3,5-difluoroisonicotinic acid, C6H3F2NO2
  76. The crystal structure of ethyl-1-(N-(adamantan-1-yl)-carbamothioyl)piperidine-4-carboxylate, C19H30N2O2S
  77. Crystal structure of 5-methyl-3-phenyl-1-tosyl-1,2,3,4-tetrahydropyridine, C19H21NO2S
  78. Crystal structure of bis((3-chlorosalicylidene)-ethylenediaminato-κ4N,N′,O,O′)nickel (II), C16H12Cl2NiN2O2
  79. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-4-hydroxybenzohydrazide — dihydrofuran-2(3H)-one (1/1), C18H17ClN2O5
  80. Crystal structure of bis((3-bromosalicylidene)-ethylenediaminato-κ4N,N′,O,O′) nickel (II), C16H12Br2NiN2O2
  81. Crystal structure of trimethylsulfoxonium tetrachloridocobaltate(II) [(CH3)3SO]2CoCl4
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