organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

Bis[4-(2,4,4-tri­methyl­pentan-2-yl)phen­yl]amine

aSchool of Chemical Engineering and Environment, North University of China, Taiyuan, People's Republic of China, and bNingbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo, People's Republic of China
*Correspondence e-mail: sliu@nimte.ac.cn

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 5 March 2016; accepted 13 March 2016; online 24 March 2016)

In the title compound, C28H43N, the dihedral angle between the aromatic rings is 41.15 (12)° and both side chains exhibit extensive disorder. No directional inter­actions beyond van der Waals contacts could be identified in the crystal.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Alkyl­ated di­phenyl­amines have been investigated extensively owing to their anti­oxidant activity (Jensen et al., 1995[Jensen, R. K., Korcek, S., Zinbo, M. & Gerlock, J. L. (1995). J. Org. Chem. 60, 5396-5400.]). Bis(4–(2,4,4–tri­methyl­penta­n–2–­yl)phen­yl)amine has been widely used in the synthesis of lubricating oil because of the reactive hydrogen atom bonded to the N atom (Hu et al., 2006[Hu, J. Q., Wei, X. Y., Yao, J. B., Han, L. & Zong, Z. M. (2006). Tribology Int. 39, 1469-1473.]; Singh et al., 2013[Singh, A., Gandra, R. T., Schnerder, E. W. & Biswas, S. K. (2013). J. Phys. Chem. 117, 1735-1742.]). The title compound was synthesized by electrophilic alkyl­ation of di­phenyl­aminde and 2,4,4–trimeth­yl–1–pentene using acid clay as catalyst (Popoff et al., 1960[Popoff, I. C., Haines, P. G. & Inman, C. E. (1960). US Patent 2943112.]) and we now report its crystal structure (Fig. 1[link]). The dihedral angle between the aromatic rings formed by atoms C1–C6 and C15–C20 is 41.15 (12)°. No directional inter­actions beyond van der Waals' contacts could be identified in the crystal (Fig. 2[link]).

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2]
Figure 2
The crystal packing of the title compound.

Synthesis and crystallization

The title compound was prepared according to a literature method (Popoff et al., 1960[Popoff, I. C., Haines, P. G. & Inman, C. E. (1960). US Patent 2943112.]). Colourless prisms were obtained by evaporation of a solution of the title compound in hexane at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. Both side chains exhibit extensive disorder.

Table 1
Experimental details

Crystal data
Chemical formula C28H43N
Mr 393.63
Crystal system, space group Monoclinic, P21/c
Temperature (K) 293
a, b, c (Å) 17.7676 (16), 13.1380 (13), 11.4852 (11)
β (°) 108.261 (2)
V3) 2546.0 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.06
Crystal size (mm) 0.21 × 0.17 × 0.12
 
Data collection
Diffractometer Bruker SMART CCD
Absorption correction Multi-scan (SADABS; Bruker, 1999[Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.639, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 14525, 4735, 2969
Rint 0.046
(sin θ/λ)max−1) 0.606
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.080, 0.268, 1.07
No. of reflections 4735
No. of parameters 340
No. of restraints 75
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.67, −0.31
Computer programs: SMART (Bruker, 1999[Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 1999[Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Experimental top

The title compound was prepared according to the literature method (Popoff et al., 1960). Colourless prisms were obtained by evaporation of a solution of the title compound in hexane at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Structure description top

Alkylated diphenylamines have been investigated extensively owing to their antioxidant activity (Jensen et al., 1995). Bis(4–(2,4,4–trimethylpentan–2–yl)phenyl)amine has been widely used in the synthesis of lubricating oil because of the reactive hydrogen atom bonded to the N atom (Hu et al., 2006; Singh et al., 2013). The title compound was synthesized by electrophilic alkylation of diphenylaminde and 2,4,4–trimethyl–1–pentene using acid clay as catalyst (Popoff et al., 1960) and we now report its crystal structure (Fig. 1). The dihedral angle between the aromatic rings formed by atoms C1–C6 and C15–C20 is 41.15(0.12)°. No directional interactions beyond van der Waals' contacts could be identified in the crystal.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound.
Bis[4-(2,4,4-trimethylpentan-2-yl)phenyl]amine top
Crystal data top
C28H43NF(000) = 872
Mr = 393.63Dx = 1.027 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.7676 (16) ÅCell parameters from 1946 reflections
b = 13.1380 (13) Åθ = 4.8–40.7°
c = 11.4852 (11) ŵ = 0.06 mm1
β = 108.261 (2)°T = 293 K
V = 2546.0 (4) Å3Prismatic, colorless
Z = 40.21 × 0.17 × 0.12 mm
Data collection top
Bruker SMART CCD
diffractometer
4735 independent reflections
Radiation source: fine-focus sealed tube2969 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
phi and ω scansθmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 2121
Tmin = 0.639, Tmax = 0.746k = 1115
14525 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.080Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.268H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.1465P)2 + 0.6321P]
where P = (Fo2 + 2Fc2)/3
4735 reflections(Δ/σ)max = 0.003
340 parametersΔρmax = 0.67 e Å3
75 restraintsΔρmin = 0.30 e Å3
Crystal data top
C28H43NV = 2546.0 (4) Å3
Mr = 393.63Z = 4
Monoclinic, P21/cMo Kα radiation
a = 17.7676 (16) ŵ = 0.06 mm1
b = 13.1380 (13) ÅT = 293 K
c = 11.4852 (11) Å0.21 × 0.17 × 0.12 mm
β = 108.261 (2)°
Data collection top
Bruker SMART CCD
diffractometer
4735 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
2969 reflections with I > 2σ(I)
Tmin = 0.639, Tmax = 0.746Rint = 0.046
14525 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.08075 restraints
wR(F2) = 0.268H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.67 e Å3
4735 reflectionsΔρmin = 0.30 e Å3
340 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.28793 (14)0.71370 (18)0.1340 (2)0.0550 (6)
H1A0.28840.74280.06720.066*
C10.33224 (15)0.6249 (2)0.1632 (2)0.0458 (6)
C20.35062 (16)0.5742 (2)0.0694 (2)0.0513 (7)
H2A0.33110.59860.01050.062*
C30.39711 (17)0.4888 (2)0.0930 (2)0.0528 (7)
H3A0.40930.45750.02860.063*
C40.42689 (15)0.4470 (2)0.2101 (2)0.0468 (7)
C50.40892 (16)0.4997 (2)0.3021 (2)0.0524 (7)
H5A0.42860.47550.38210.063*
C60.36305 (17)0.5864 (2)0.2803 (2)0.0533 (7)
H6A0.35280.61950.34530.064*
C70.47709 (17)0.3505 (2)0.2313 (3)0.0559 (8)
C80.5460 (2)0.3688 (3)0.1771 (4)0.0851 (11)
H8A0.57790.42480.21870.128*
H8B0.52460.38410.09130.128*
H8C0.57820.30870.18780.128*
C90.5169 (2)0.3290 (3)0.3654 (3)0.0810 (11)
H9A0.47730.31590.40440.121*
H9B0.54800.38690.40320.121*
H9C0.55060.27060.37410.121*
C100.4322 (2)0.2591 (3)0.1546 (3)0.0704 (9)
H10A0.47000.20370.16760.085*
H10B0.41940.27860.06920.085*
C110.3549 (2)0.2131 (3)0.1704 (3)0.0706 (9)
C120.2868 (3)0.2861 (4)0.1300 (7)0.142 (2)
H12A0.23820.24870.09820.213*
H12B0.29380.32970.06710.213*
H12C0.28480.32650.19850.213*
C130.3370 (3)0.1250 (4)0.0808 (4)0.1120 (15)
H13A0.35750.13980.01460.168*
H13B0.28070.11520.04890.168*
H13C0.36150.06430.12200.168*
C140.3689 (5)0.1698 (6)0.2948 (5)0.144 (3)0.797 (10)
H14A0.42260.18290.34400.215*0.797 (10)
H14B0.35970.09770.28860.215*0.797 (10)
H14C0.33330.20090.33230.215*0.797 (10)
C14'0.304 (2)0.148 (3)0.261 (2)0.146 (5)0.203 (10)
H14D0.33940.13910.34290.219*0.203 (10)
H14E0.28630.08300.22530.219*0.203 (10)
H14F0.25920.18800.26370.219*0.203 (10)
C150.24268 (15)0.7629 (2)0.1969 (2)0.0479 (7)
C160.21175 (16)0.7158 (2)0.2791 (3)0.0536 (7)
H16A0.22350.64780.29930.064*
C170.16335 (17)0.7687 (2)0.3318 (3)0.0569 (8)
H17A0.14340.73500.38700.068*
C180.14367 (16)0.8692 (2)0.3055 (3)0.0581 (8)
C190.17542 (18)0.9152 (2)0.2240 (3)0.0651 (8)
H19A0.16350.98310.20370.078*
C200.22417 (17)0.8643 (2)0.1714 (3)0.0609 (8)
H20A0.24500.89870.11780.073*
C210.08906 (19)0.9284 (3)0.3625 (3)0.0727 (10)
C220.0681 (4)0.8611 (6)0.4614 (5)0.122 (3)0.779 (6)
H22A0.11430.85330.53170.183*0.779 (6)
H22B0.05020.79530.42720.183*0.779 (6)
H22C0.02690.89350.48550.183*0.779 (6)
C230.1356 (4)1.0216 (6)0.4278 (8)0.125 (3)0.779 (6)
H23A0.14821.06460.36900.187*0.779 (6)
H23B0.18360.99970.48810.187*0.779 (6)
H23C0.10391.05900.46730.187*0.779 (6)
C240.0145 (3)0.9664 (4)0.2669 (4)0.0736 (14)0.779 (6)
H24A0.03181.00850.21080.088*0.779 (6)
H24B0.01131.01170.30930.088*0.779 (6)
C250.0511 (6)0.8954 (9)0.1864 (9)0.0969 (17)0.779 (6)
C260.1080 (6)0.9765 (8)0.1194 (10)0.159 (3)0.779 (6)
H26A0.15360.94510.06250.238*0.779 (6)
H26B0.08251.01950.07560.238*0.779 (6)
H26C0.12421.01650.17720.238*0.779 (6)
C270.0214 (6)0.8335 (7)0.1007 (7)0.110 (3)0.779 (6)
H27A0.06310.79030.05250.165*0.779 (6)
H27B0.02240.79240.14710.165*0.779 (6)
H27C0.00440.87800.04760.165*0.779 (6)
C280.0974 (6)0.8275 (8)0.2440 (10)0.158 (3)0.779 (6)
H28A0.13470.78840.18140.236*0.779 (6)
H28B0.12520.86820.28660.236*0.779 (6)
H28C0.06170.78230.30090.236*0.779 (6)
C22'0.1271 (14)0.943 (2)0.4881 (18)0.105 (7)0.221 (6)
H22D0.16350.99920.49950.158*0.221 (6)
H22E0.15550.88270.52280.158*0.221 (6)
H22F0.08830.95820.52800.158*0.221 (6)
C23'0.0859 (14)1.0473 (14)0.325 (2)0.100 (7)0.221 (6)
H23D0.06141.08550.37480.150*0.221 (6)
H23E0.05571.05510.24040.150*0.221 (6)
H23F0.13881.07200.33860.150*0.221 (6)
C24'0.0065 (7)0.8881 (15)0.3270 (13)0.074 (4)0.221 (6)
H24C0.01980.92010.37980.088*0.221 (6)
H24D0.00980.81590.34570.088*0.221 (6)
C25'0.0504 (14)0.901 (3)0.1871 (19)0.073 (4)0.221 (6)
C26'0.0986 (13)0.961 (2)0.0669 (16)0.081 (5)0.221 (6)
H26D0.13080.91370.00840.122*0.221 (6)
H26E0.06230.99390.03240.122*0.221 (6)
H26F0.13191.01080.08710.122*0.221 (6)
C27'0.0232 (17)0.804 (2)0.136 (2)0.077 (5)0.221 (6)
H27D0.05030.79840.04980.116*0.221 (6)
H27E0.03550.74510.17720.116*0.221 (6)
H27F0.03290.80650.15020.116*0.221 (6)
C28'0.1175 (10)0.8818 (18)0.242 (2)0.079 (4)0.221 (6)
H28D0.16770.88930.17900.118*0.221 (6)
H28E0.11390.92990.30620.118*0.221 (6)
H28F0.11290.81400.27440.118*0.221 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0585 (14)0.0524 (14)0.0599 (14)0.0138 (11)0.0269 (12)0.0090 (11)
C10.0435 (14)0.0441 (14)0.0515 (15)0.0001 (12)0.0171 (12)0.0014 (12)
C20.0581 (17)0.0544 (16)0.0452 (15)0.0056 (13)0.0216 (13)0.0056 (13)
C30.0643 (18)0.0514 (16)0.0485 (16)0.0060 (14)0.0261 (13)0.0022 (13)
C40.0454 (14)0.0461 (15)0.0492 (15)0.0022 (12)0.0152 (12)0.0017 (12)
C50.0541 (16)0.0578 (17)0.0421 (14)0.0082 (13)0.0103 (12)0.0016 (13)
C60.0591 (17)0.0538 (16)0.0458 (15)0.0070 (14)0.0149 (13)0.0099 (13)
C70.0544 (17)0.0501 (16)0.0604 (18)0.0084 (13)0.0141 (14)0.0005 (14)
C80.077 (2)0.091 (3)0.096 (3)0.027 (2)0.040 (2)0.008 (2)
C90.091 (3)0.083 (2)0.063 (2)0.037 (2)0.0160 (18)0.0093 (18)
C100.085 (2)0.063 (2)0.068 (2)0.0137 (18)0.0291 (17)0.0046 (16)
C110.082 (2)0.063 (2)0.068 (2)0.0060 (17)0.0243 (17)0.0004 (16)
C120.074 (3)0.091 (3)0.266 (8)0.008 (3)0.061 (4)0.019 (4)
C130.143 (4)0.089 (3)0.102 (3)0.015 (3)0.036 (3)0.011 (3)
C140.177 (7)0.186 (7)0.075 (4)0.105 (6)0.051 (4)0.001 (4)
C14'0.177 (11)0.185 (10)0.082 (8)0.099 (10)0.052 (8)0.010 (8)
C150.0404 (14)0.0460 (15)0.0553 (16)0.0033 (12)0.0120 (12)0.0025 (12)
C160.0554 (17)0.0458 (15)0.0608 (17)0.0045 (13)0.0202 (14)0.0003 (13)
C170.0546 (16)0.0621 (18)0.0564 (17)0.0069 (14)0.0208 (14)0.0024 (14)
C180.0466 (16)0.067 (2)0.0577 (17)0.0097 (14)0.0116 (13)0.0084 (15)
C190.0601 (18)0.0482 (17)0.086 (2)0.0135 (14)0.0207 (17)0.0009 (16)
C200.0551 (17)0.0533 (17)0.078 (2)0.0048 (14)0.0265 (15)0.0083 (15)
C210.064 (2)0.083 (2)0.068 (2)0.0249 (18)0.0157 (16)0.0131 (18)
C220.135 (5)0.175 (7)0.079 (4)0.092 (5)0.067 (4)0.042 (4)
C230.082 (4)0.139 (6)0.136 (6)0.021 (4)0.008 (4)0.082 (5)
C240.066 (2)0.081 (3)0.076 (3)0.017 (2)0.025 (2)0.006 (2)
C250.077 (3)0.113 (3)0.096 (3)0.008 (3)0.022 (3)0.016 (3)
C260.120 (5)0.159 (6)0.166 (7)0.040 (5)0.000 (5)0.018 (6)
C270.094 (4)0.136 (6)0.088 (5)0.000 (5)0.010 (4)0.036 (4)
C280.153 (6)0.176 (7)0.146 (6)0.015 (6)0.050 (5)0.001 (6)
C22'0.097 (10)0.119 (11)0.110 (10)0.020 (9)0.049 (8)0.033 (8)
C23'0.108 (10)0.086 (9)0.113 (10)0.013 (8)0.047 (8)0.021 (8)
C24'0.051 (6)0.111 (9)0.065 (6)0.008 (6)0.025 (5)0.001 (6)
C25'0.045 (5)0.112 (8)0.065 (6)0.005 (5)0.024 (5)0.002 (6)
C26'0.059 (7)0.121 (10)0.059 (7)0.007 (7)0.013 (6)0.010 (7)
C27'0.048 (7)0.112 (10)0.068 (9)0.011 (7)0.012 (7)0.004 (8)
C28'0.045 (6)0.113 (10)0.085 (8)0.009 (7)0.031 (6)0.015 (8)
Geometric parameters (Å, º) top
N1—C11.389 (3)C19—H19A0.9300
N1—C151.396 (3)C20—H20A0.9300
N1—H1A0.8600C21—C22'1.40 (2)
C1—C61.378 (4)C21—C24'1.491 (12)
C1—C21.390 (4)C21—C241.516 (5)
C2—C31.369 (4)C21—C231.536 (7)
C2—H2A0.9300C21—C221.574 (7)
C3—C41.395 (4)C21—C23'1.615 (19)
C3—H3A0.9300C22—H22A0.9600
C4—C51.382 (4)C22—H22B0.9600
C4—C71.525 (4)C22—H22C0.9600
C5—C61.378 (4)C23—H23A0.9600
C5—H5A0.9300C23—H23B0.9600
C6—H6A0.9300C23—H23C0.9600
C7—C91.507 (4)C24—C251.553 (13)
C7—C101.554 (4)C24—H24A0.9700
C7—C81.557 (4)C24—H24B0.9700
C8—H8A0.9600C25—C271.495 (10)
C8—H8B0.9600C25—C281.500 (11)
C8—H8C0.9600C25—C261.503 (10)
C9—H9A0.9600C26—H26A0.9600
C9—H9B0.9600C26—H26B0.9600
C9—H9C0.9600C26—H26C0.9600
C10—C111.562 (5)C27—H27A0.9600
C10—H10A0.9700C27—H27B0.9600
C10—H10B0.9700C27—H27C0.9600
C11—C141.484 (6)C28—H28A0.9600
C11—C121.498 (6)C28—H28B0.9600
C11—C131.515 (5)C28—H28C0.9600
C11—C14'1.79 (2)C22'—H22D0.9600
C12—H12A0.9600C22'—H22E0.9600
C12—H12B0.9600C22'—H22F0.9600
C12—H12C0.9600C23'—H23D0.9600
C13—H13A0.9600C23'—H23E0.9600
C13—H13B0.9600C23'—H23F0.9600
C13—H13C0.9600C24'—C25'1.617 (19)
C14—H14A0.9600C24'—H24C0.9700
C14—H14B0.9600C24'—H24D0.9700
C14—H14C0.9600C25'—C28'1.534 (19)
C14'—H14D0.9600C25'—C27'1.55 (2)
C14'—H14E0.9600C25'—C26'1.583 (18)
C14'—H14F0.9600C26'—H26D0.9600
C15—C161.379 (4)C26'—H26E0.9600
C15—C201.381 (4)C26'—H26F0.9600
C16—C171.384 (4)C27'—H27D0.9600
C16—H16A0.9300C27'—H27E0.9600
C17—C181.375 (4)C27'—H27F0.9600
C17—H17A0.9300C28'—H28D0.9600
C18—C191.376 (4)C28'—H28E0.9600
C18—C211.540 (4)C28'—H28F0.9600
C19—C201.375 (4)
C1—N1—C15129.7 (2)C22'—C21—C24136.8 (9)
C1—N1—H1A115.2C24'—C21—C2450.0 (7)
C15—N1—H1A115.2C22'—C21—C2351.2 (11)
C6—C1—N1124.4 (2)C24'—C21—C23138.5 (7)
C6—C1—C2117.6 (2)C24—C21—C23107.8 (4)
N1—C1—C2117.9 (2)C22'—C21—C18110.0 (9)
C3—C2—C1120.8 (3)C24'—C21—C18113.7 (7)
C3—C2—H2A119.6C24—C21—C18112.5 (3)
C1—C2—H2A119.6C23—C21—C18107.3 (3)
C2—C3—C4122.5 (2)C22'—C21—C2258.8 (11)
C2—C3—H3A118.7C24'—C21—C2264.1 (7)
C4—C3—H3A118.7C24—C21—C22110.9 (4)
C5—C4—C3115.6 (2)C23—C21—C22108.0 (5)
C5—C4—C7123.9 (2)C18—C21—C22110.2 (3)
C3—C4—C7120.5 (2)C22'—C21—C23'95.9 (11)
C6—C5—C4122.7 (3)C24'—C21—C23'108.8 (11)
C6—C5—H5A118.7C24—C21—C23'62.6 (9)
C4—C5—H5A118.7C23—C21—C23'47.7 (8)
C5—C6—C1120.8 (2)C18—C21—C23'110.5 (7)
C5—C6—H6A119.6C22—C21—C23'137.5 (7)
C1—C6—H6A119.6C21—C22—H22A109.5
C9—C7—C4112.5 (2)C21—C22—H22B109.5
C9—C7—C10115.3 (3)C21—C22—H22C109.5
C4—C7—C10112.4 (2)C21—C23—H23A109.5
C9—C7—C8105.2 (3)C21—C23—H23B109.5
C4—C7—C8107.6 (2)H23A—C23—H23B109.5
C10—C7—C8102.8 (3)C21—C23—H23C109.5
C7—C8—H8A109.5H23A—C23—H23C109.5
C7—C8—H8B109.5H23B—C23—H23C109.5
H8A—C8—H8B109.5C21—C24—C25123.8 (5)
C7—C8—H8C109.5C21—C24—H24A106.4
H8A—C8—H8C109.5C25—C24—H24A106.4
H8B—C8—H8C109.5C21—C24—H24B106.4
C7—C9—H9A109.5C25—C24—H24B106.4
C7—C9—H9B109.5H24A—C24—H24B106.5
H9A—C9—H9B109.5C27—C25—C28108.8 (9)
C7—C9—H9C109.5C27—C25—C26111.6 (8)
H9A—C9—H9C109.5C28—C25—C26105.9 (9)
H9B—C9—H9C109.5C27—C25—C24111.4 (8)
C7—C10—C11123.2 (3)C28—C25—C24120.5 (8)
C7—C10—H10A106.5C26—C25—C2497.9 (8)
C11—C10—H10A106.5C25—C26—H26A109.5
C7—C10—H10B106.5C25—C26—H26B109.5
C11—C10—H10B106.5H26A—C26—H26B109.5
H10A—C10—H10B106.5C25—C26—H26C109.5
C14—C11—C12114.8 (5)H26A—C26—H26C109.5
C14—C11—C13107.3 (4)H26B—C26—H26C109.5
C12—C11—C13107.5 (4)C25—C27—H27A109.5
C14—C11—C10111.8 (4)C25—C27—H27B109.5
C12—C11—C10111.7 (3)H27A—C27—H27B109.5
C13—C11—C10102.8 (3)C25—C27—H27C109.5
C14—C11—C14'38.9 (10)H27A—C27—H27C109.5
C12—C11—C14'88.8 (13)H27B—C27—H27C109.5
C13—C11—C14'89.7 (10)C25—C28—H28A109.5
C10—C11—C14'150.7 (11)C25—C28—H28B109.5
C11—C12—H12A109.5H28A—C28—H28B109.5
C11—C12—H12B109.5C25—C28—H28C109.5
H12A—C12—H12B109.5H28A—C28—H28C109.5
C11—C12—H12C109.5H28B—C28—H28C109.5
H12A—C12—H12C109.5C21—C22'—H22D109.5
H12B—C12—H12C109.5C21—C22'—H22E109.5
C11—C13—H13A109.5H22D—C22'—H22E109.5
C11—C13—H13B109.5C21—C22'—H22F109.5
H13A—C13—H13B109.5H22D—C22'—H22F109.5
C11—C13—H13C109.5H22E—C22'—H22F109.5
H13A—C13—H13C109.5C21—C23'—H23D109.5
H13B—C13—H13C109.5C21—C23'—H23E109.5
C11—C14—H14A109.5C21—C23'—H23F109.5
C11—C14—H14B109.5C21—C24'—C25'119.2 (14)
H14A—C14—H14B109.5C21—C24'—H24C107.5
C11—C14—H14C109.5C25'—C24'—H24C107.5
H14A—C14—H14C109.5C21—C24'—H24D107.5
H14B—C14—H14C109.5C25'—C24'—H24D107.5
C11—C14'—H14D109.5H24C—C24'—H24D107.0
C11—C14'—H14E109.5C28'—C25'—C27'113 (2)
H14D—C14'—H14E109.5C28'—C25'—C26'99.3 (17)
C11—C14'—H14F109.5C27'—C25'—C26'103.2 (19)
H14D—C14'—H14F109.5C28'—C25'—C24'84.2 (13)
H14E—C14'—H14F109.5C27'—C25'—C24'96.5 (17)
C16—C15—C20117.3 (3)C26'—C25'—C24'157 (3)
C16—C15—N1124.3 (2)C25'—C26'—H26D109.5
C20—C15—N1118.3 (3)C25'—C26'—H26E109.5
C15—C16—C17120.6 (3)H26D—C26'—H26E109.5
C15—C16—H16A119.7C25'—C26'—H26F109.5
C17—C16—H16A119.7H26D—C26'—H26F109.5
C18—C17—C16122.5 (3)H26E—C26'—H26F109.5
C18—C17—H17A118.8C25'—C27'—H27D109.5
C16—C17—H17A118.8C25'—C27'—H27E109.5
C17—C18—C19116.2 (3)H27D—C27'—H27E109.5
C17—C18—C21122.9 (3)C25'—C27'—H27F109.5
C19—C18—C21121.0 (3)H27D—C27'—H27F109.5
C20—C19—C18122.3 (3)H27E—C27'—H27F109.5
C20—C19—H19A118.9C25'—C28'—H28D109.5
C18—C19—H19A118.9C25'—C28'—H28E109.5
C19—C20—C15121.2 (3)H28D—C28'—H28E109.5
C19—C20—H20A119.4C25'—C28'—H28F109.5
C15—C20—H20A119.4H28D—C28'—H28F109.5
C22'—C21—C24'116.5 (12)H28E—C28'—H28F109.5
C15—N1—C1—C624.3 (4)C18—C19—C20—C151.1 (5)
C15—N1—C1—C2159.5 (3)C16—C15—C20—C191.4 (4)
C6—C1—C2—C30.5 (4)N1—C15—C20—C19175.6 (3)
N1—C1—C2—C3177.0 (2)C17—C18—C21—C22'68.8 (14)
C1—C2—C3—C41.4 (4)C19—C18—C21—C22'111.5 (13)
C2—C3—C4—C52.4 (4)C17—C18—C21—C24'63.9 (8)
C2—C3—C4—C7178.8 (3)C19—C18—C21—C24'115.8 (8)
C3—C4—C5—C61.5 (4)C17—C18—C21—C24118.6 (4)
C7—C4—C5—C6179.7 (3)C19—C18—C21—C2461.1 (4)
C4—C5—C6—C10.3 (4)C17—C18—C21—C23123.0 (5)
N1—C1—C6—C5177.6 (3)C19—C18—C21—C2357.3 (5)
C2—C1—C6—C51.4 (4)C17—C18—C21—C225.7 (5)
C5—C4—C7—C910.1 (4)C19—C18—C21—C22174.6 (4)
C3—C4—C7—C9168.6 (3)C17—C18—C21—C23'173.5 (10)
C5—C4—C7—C10122.0 (3)C19—C18—C21—C23'6.8 (10)
C3—C4—C7—C1059.2 (4)C22'—C21—C24—C25124.4 (19)
C5—C4—C7—C8125.5 (3)C24'—C21—C24—C2536.8 (10)
C3—C4—C7—C853.2 (4)C23—C21—C24—C25176.1 (6)
C9—C7—C10—C1168.5 (4)C18—C21—C24—C2565.9 (7)
C4—C7—C10—C1162.2 (4)C22—C21—C24—C2558.1 (7)
C8—C7—C10—C11177.7 (3)C23'—C21—C24—C25168.1 (10)
C7—C10—C11—C1462.9 (5)C21—C24—C25—C2766.0 (9)
C7—C10—C11—C1267.3 (5)C21—C24—C25—C2863.2 (10)
C7—C10—C11—C13177.7 (3)C21—C24—C25—C26177.0 (6)
C7—C10—C11—C14'64 (2)C22'—C21—C24'—C25'161.2 (18)
C1—N1—C15—C1622.9 (5)C24—C21—C24'—C25'31.0 (15)
C1—N1—C15—C20160.4 (3)C23—C21—C24'—C25'100.7 (17)
C20—C15—C16—C170.8 (4)C18—C21—C24'—C25'69.3 (19)
N1—C15—C16—C17175.9 (3)C22—C21—C24'—C25'171.2 (19)
C15—C16—C17—C180.1 (4)C23'—C21—C24'—C25'54.2 (19)
C16—C17—C18—C190.5 (4)C21—C24'—C25'—C28'161.1 (16)
C16—C17—C18—C21179.3 (3)C21—C24'—C25'—C27'86 (2)
C17—C18—C19—C200.1 (5)C21—C24'—C25'—C26'61 (5)
C21—C18—C19—C20179.8 (3)

Experimental details

Crystal data
Chemical formulaC28H43N
Mr393.63
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)17.7676 (16), 13.1380 (13), 11.4852 (11)
β (°) 108.261 (2)
V3)2546.0 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.06
Crystal size (mm)0.21 × 0.17 × 0.12
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.639, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
14525, 4735, 2969
Rint0.046
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.080, 0.268, 1.07
No. of reflections4735
No. of parameters340
No. of restraints75
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.67, 0.30

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

 

Acknowledgements

The authors thank National Science Foundation of China (No. 21404114) for financial support.

References

First citationBruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHu, J. Q., Wei, X. Y., Yao, J. B., Han, L. & Zong, Z. M. (2006). Tribology Int. 39, 1469–1473.  CrossRef CAS Google Scholar
First citationJensen, R. K., Korcek, S., Zinbo, M. & Gerlock, J. L. (1995). J. Org. Chem. 60, 5396–5400.  CrossRef CAS Google Scholar
First citationPopoff, I. C., Haines, P. G. & Inman, C. E. (1960). US Patent 2943112.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSingh, A., Gandra, R. T., Schnerder, E. W. & Biswas, S. K. (2013). J. Phys. Chem. 117, 1735–1742.  CAS Google Scholar

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