organic compounds
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
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.
CCDC reference: 1465157
Structure description
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 (Fig. 1). 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).
Synthesis and crystallization
The title compound was prepared according to a 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
Crystal data, data collection and structure . Both side chains exhibit extensive disorder.
details are summarized in Table 1Structural data
CCDC reference: 1465157
10.1107/S2414314616004247/hb4027sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616004247/hb4027Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616004247/hb4027Isup3.cml
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.
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
(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.Data collection: SMART (Bruker, 1999); cell
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).Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. The crystal packing of the title compound. |
C28H43N | F(000) = 872 |
Mr = 393.63 | Dx = 1.027 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.7676 (16) Å | Cell parameters from 1946 reflections |
b = 13.1380 (13) Å | θ = 4.8–40.7° |
c = 11.4852 (11) Å | µ = 0.06 mm−1 |
β = 108.261 (2)° | T = 293 K |
V = 2546.0 (4) Å3 | Prismatic, colorless |
Z = 4 | 0.21 × 0.17 × 0.12 mm |
Bruker SMART CCD diffractometer | 4735 independent reflections |
Radiation source: fine-focus sealed tube | 2969 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
phi and ω scans | θmax = 25.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −21→21 |
Tmin = 0.639, Tmax = 0.746 | k = −11→15 |
14525 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.268 | H 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 parameters | Δρmax = 0.67 e Å−3 |
75 restraints | Δρmin = −0.30 e Å−3 |
C28H43N | V = 2546.0 (4) Å3 |
Mr = 393.63 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.7676 (16) Å | µ = 0.06 mm−1 |
b = 13.1380 (13) Å | T = 293 K |
c = 11.4852 (11) Å | 0.21 × 0.17 × 0.12 mm |
β = 108.261 (2)° |
Bruker SMART CCD diffractometer | 4735 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 2969 reflections with I > 2σ(I) |
Tmin = 0.639, Tmax = 0.746 | Rint = 0.046 |
14525 measured reflections |
R[F2 > 2σ(F2)] = 0.080 | 75 restraints |
wR(F2) = 0.268 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.67 e Å−3 |
4735 reflections | Δρmin = −0.30 e Å−3 |
340 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.28793 (14) | 0.71370 (18) | 0.1340 (2) | 0.0550 (6) | |
H1A | 0.2884 | 0.7428 | 0.0672 | 0.066* | |
C1 | 0.33224 (15) | 0.6249 (2) | 0.1632 (2) | 0.0458 (6) | |
C2 | 0.35062 (16) | 0.5742 (2) | 0.0694 (2) | 0.0513 (7) | |
H2A | 0.3311 | 0.5986 | −0.0105 | 0.062* | |
C3 | 0.39711 (17) | 0.4888 (2) | 0.0930 (2) | 0.0528 (7) | |
H3A | 0.4093 | 0.4575 | 0.0286 | 0.063* | |
C4 | 0.42689 (15) | 0.4470 (2) | 0.2101 (2) | 0.0468 (7) | |
C5 | 0.40892 (16) | 0.4997 (2) | 0.3021 (2) | 0.0524 (7) | |
H5A | 0.4286 | 0.4755 | 0.3821 | 0.063* | |
C6 | 0.36305 (17) | 0.5864 (2) | 0.2803 (2) | 0.0533 (7) | |
H6A | 0.3528 | 0.6195 | 0.3453 | 0.064* | |
C7 | 0.47709 (17) | 0.3505 (2) | 0.2313 (3) | 0.0559 (8) | |
C8 | 0.5460 (2) | 0.3688 (3) | 0.1771 (4) | 0.0851 (11) | |
H8A | 0.5779 | 0.4248 | 0.2187 | 0.128* | |
H8B | 0.5246 | 0.3841 | 0.0913 | 0.128* | |
H8C | 0.5782 | 0.3087 | 0.1878 | 0.128* | |
C9 | 0.5169 (2) | 0.3290 (3) | 0.3654 (3) | 0.0810 (11) | |
H9A | 0.4773 | 0.3159 | 0.4044 | 0.121* | |
H9B | 0.5480 | 0.3869 | 0.4032 | 0.121* | |
H9C | 0.5506 | 0.2706 | 0.3741 | 0.121* | |
C10 | 0.4322 (2) | 0.2591 (3) | 0.1546 (3) | 0.0704 (9) | |
H10A | 0.4700 | 0.2037 | 0.1676 | 0.085* | |
H10B | 0.4194 | 0.2786 | 0.0692 | 0.085* | |
C11 | 0.3549 (2) | 0.2131 (3) | 0.1704 (3) | 0.0706 (9) | |
C12 | 0.2868 (3) | 0.2861 (4) | 0.1300 (7) | 0.142 (2) | |
H12A | 0.2382 | 0.2487 | 0.0982 | 0.213* | |
H12B | 0.2938 | 0.3297 | 0.0671 | 0.213* | |
H12C | 0.2848 | 0.3265 | 0.1985 | 0.213* | |
C13 | 0.3370 (3) | 0.1250 (4) | 0.0808 (4) | 0.1120 (15) | |
H13A | 0.3575 | 0.1398 | 0.0146 | 0.168* | |
H13B | 0.2807 | 0.1152 | 0.0489 | 0.168* | |
H13C | 0.3615 | 0.0643 | 0.1220 | 0.168* | |
C14 | 0.3689 (5) | 0.1698 (6) | 0.2948 (5) | 0.144 (3) | 0.797 (10) |
H14A | 0.4226 | 0.1829 | 0.3440 | 0.215* | 0.797 (10) |
H14B | 0.3597 | 0.0977 | 0.2886 | 0.215* | 0.797 (10) |
H14C | 0.3333 | 0.2009 | 0.3323 | 0.215* | 0.797 (10) |
C14' | 0.304 (2) | 0.148 (3) | 0.261 (2) | 0.146 (5) | 0.203 (10) |
H14D | 0.3394 | 0.1391 | 0.3429 | 0.219* | 0.203 (10) |
H14E | 0.2863 | 0.0830 | 0.2253 | 0.219* | 0.203 (10) |
H14F | 0.2592 | 0.1880 | 0.2637 | 0.219* | 0.203 (10) |
C15 | 0.24268 (15) | 0.7629 (2) | 0.1969 (2) | 0.0479 (7) | |
C16 | 0.21175 (16) | 0.7158 (2) | 0.2791 (3) | 0.0536 (7) | |
H16A | 0.2235 | 0.6478 | 0.2993 | 0.064* | |
C17 | 0.16335 (17) | 0.7687 (2) | 0.3318 (3) | 0.0569 (8) | |
H17A | 0.1434 | 0.7350 | 0.3870 | 0.068* | |
C18 | 0.14367 (16) | 0.8692 (2) | 0.3055 (3) | 0.0581 (8) | |
C19 | 0.17542 (18) | 0.9152 (2) | 0.2240 (3) | 0.0651 (8) | |
H19A | 0.1635 | 0.9831 | 0.2037 | 0.078* | |
C20 | 0.22417 (17) | 0.8643 (2) | 0.1714 (3) | 0.0609 (8) | |
H20A | 0.2450 | 0.8987 | 0.1178 | 0.073* | |
C21 | 0.08906 (19) | 0.9284 (3) | 0.3625 (3) | 0.0727 (10) | |
C22 | 0.0681 (4) | 0.8611 (6) | 0.4614 (5) | 0.122 (3) | 0.779 (6) |
H22A | 0.1143 | 0.8533 | 0.5317 | 0.183* | 0.779 (6) |
H22B | 0.0502 | 0.7953 | 0.4272 | 0.183* | 0.779 (6) |
H22C | 0.0269 | 0.8935 | 0.4855 | 0.183* | 0.779 (6) |
C23 | 0.1356 (4) | 1.0216 (6) | 0.4278 (8) | 0.125 (3) | 0.779 (6) |
H23A | 0.1482 | 1.0646 | 0.3690 | 0.187* | 0.779 (6) |
H23B | 0.1836 | 0.9997 | 0.4881 | 0.187* | 0.779 (6) |
H23C | 0.1039 | 1.0590 | 0.4673 | 0.187* | 0.779 (6) |
C24 | 0.0145 (3) | 0.9664 (4) | 0.2669 (4) | 0.0736 (14) | 0.779 (6) |
H24A | 0.0318 | 1.0085 | 0.2108 | 0.088* | 0.779 (6) |
H24B | −0.0113 | 1.0117 | 0.3093 | 0.088* | 0.779 (6) |
C25 | −0.0511 (6) | 0.8954 (9) | 0.1864 (9) | 0.0969 (17) | 0.779 (6) |
C26 | −0.1080 (6) | 0.9765 (8) | 0.1194 (10) | 0.159 (3) | 0.779 (6) |
H26A | −0.1536 | 0.9451 | 0.0625 | 0.238* | 0.779 (6) |
H26B | −0.0825 | 1.0195 | 0.0756 | 0.238* | 0.779 (6) |
H26C | −0.1242 | 1.0165 | 0.1772 | 0.238* | 0.779 (6) |
C27 | −0.0214 (6) | 0.8335 (7) | 0.1007 (7) | 0.110 (3) | 0.779 (6) |
H27A | −0.0631 | 0.7903 | 0.0525 | 0.165* | 0.779 (6) |
H27B | 0.0224 | 0.7924 | 0.1471 | 0.165* | 0.779 (6) |
H27C | −0.0044 | 0.8780 | 0.0476 | 0.165* | 0.779 (6) |
C28 | −0.0974 (6) | 0.8275 (8) | 0.2440 (10) | 0.158 (3) | 0.779 (6) |
H28A | −0.1347 | 0.7884 | 0.1814 | 0.236* | 0.779 (6) |
H28B | −0.1252 | 0.8682 | 0.2866 | 0.236* | 0.779 (6) |
H28C | −0.0617 | 0.7823 | 0.3009 | 0.236* | 0.779 (6) |
C22' | 0.1271 (14) | 0.943 (2) | 0.4881 (18) | 0.105 (7) | 0.221 (6) |
H22D | 0.1635 | 0.9992 | 0.4995 | 0.158* | 0.221 (6) |
H22E | 0.1555 | 0.8827 | 0.5228 | 0.158* | 0.221 (6) |
H22F | 0.0883 | 0.9582 | 0.5280 | 0.158* | 0.221 (6) |
C23' | 0.0859 (14) | 1.0473 (14) | 0.325 (2) | 0.100 (7) | 0.221 (6) |
H23D | 0.0614 | 1.0855 | 0.3748 | 0.150* | 0.221 (6) |
H23E | 0.0557 | 1.0551 | 0.2404 | 0.150* | 0.221 (6) |
H23F | 0.1388 | 1.0720 | 0.3386 | 0.150* | 0.221 (6) |
C24' | 0.0065 (7) | 0.8881 (15) | 0.3270 (13) | 0.074 (4) | 0.221 (6) |
H24C | −0.0198 | 0.9201 | 0.3798 | 0.088* | 0.221 (6) |
H24D | 0.0098 | 0.8159 | 0.3457 | 0.088* | 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) |
H26D | −0.1308 | 0.9137 | 0.0084 | 0.122* | 0.221 (6) |
H26E | −0.0623 | 0.9939 | 0.0324 | 0.122* | 0.221 (6) |
H26F | −0.1319 | 1.0108 | 0.0871 | 0.122* | 0.221 (6) |
C27' | −0.0232 (17) | 0.804 (2) | 0.136 (2) | 0.077 (5) | 0.221 (6) |
H27D | −0.0503 | 0.7984 | 0.0498 | 0.116* | 0.221 (6) |
H27E | −0.0355 | 0.7451 | 0.1772 | 0.116* | 0.221 (6) |
H27F | 0.0329 | 0.8065 | 0.1502 | 0.116* | 0.221 (6) |
C28' | −0.1175 (10) | 0.8818 (18) | 0.242 (2) | 0.079 (4) | 0.221 (6) |
H28D | −0.1677 | 0.8893 | 0.1790 | 0.118* | 0.221 (6) |
H28E | −0.1139 | 0.9299 | 0.3062 | 0.118* | 0.221 (6) |
H28F | −0.1129 | 0.8140 | 0.2744 | 0.118* | 0.221 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0585 (14) | 0.0524 (14) | 0.0599 (14) | 0.0138 (11) | 0.0269 (12) | 0.0090 (11) |
C1 | 0.0435 (14) | 0.0441 (14) | 0.0515 (15) | 0.0001 (12) | 0.0171 (12) | −0.0014 (12) |
C2 | 0.0581 (17) | 0.0544 (16) | 0.0452 (15) | 0.0056 (13) | 0.0216 (13) | 0.0056 (13) |
C3 | 0.0643 (18) | 0.0514 (16) | 0.0485 (16) | 0.0060 (14) | 0.0261 (13) | −0.0022 (13) |
C4 | 0.0454 (14) | 0.0461 (15) | 0.0492 (15) | 0.0022 (12) | 0.0152 (12) | −0.0017 (12) |
C5 | 0.0541 (16) | 0.0578 (17) | 0.0421 (14) | 0.0082 (13) | 0.0103 (12) | −0.0016 (13) |
C6 | 0.0591 (17) | 0.0538 (16) | 0.0458 (15) | 0.0070 (14) | 0.0149 (13) | −0.0099 (13) |
C7 | 0.0544 (17) | 0.0501 (16) | 0.0604 (18) | 0.0084 (13) | 0.0141 (14) | 0.0005 (14) |
C8 | 0.077 (2) | 0.091 (3) | 0.096 (3) | 0.027 (2) | 0.040 (2) | 0.008 (2) |
C9 | 0.091 (3) | 0.083 (2) | 0.063 (2) | 0.037 (2) | 0.0160 (18) | 0.0093 (18) |
C10 | 0.085 (2) | 0.063 (2) | 0.068 (2) | 0.0137 (18) | 0.0291 (17) | 0.0046 (16) |
C11 | 0.082 (2) | 0.063 (2) | 0.068 (2) | −0.0060 (17) | 0.0243 (17) | −0.0004 (16) |
C12 | 0.074 (3) | 0.091 (3) | 0.266 (8) | −0.008 (3) | 0.061 (4) | −0.019 (4) |
C13 | 0.143 (4) | 0.089 (3) | 0.102 (3) | −0.015 (3) | 0.036 (3) | −0.011 (3) |
C14 | 0.177 (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) |
C15 | 0.0404 (14) | 0.0460 (15) | 0.0553 (16) | 0.0033 (12) | 0.0120 (12) | −0.0025 (12) |
C16 | 0.0554 (17) | 0.0458 (15) | 0.0608 (17) | 0.0045 (13) | 0.0202 (14) | 0.0003 (13) |
C17 | 0.0546 (16) | 0.0621 (18) | 0.0564 (17) | 0.0069 (14) | 0.0208 (14) | 0.0024 (14) |
C18 | 0.0466 (16) | 0.067 (2) | 0.0577 (17) | 0.0097 (14) | 0.0116 (13) | −0.0084 (15) |
C19 | 0.0601 (18) | 0.0482 (17) | 0.086 (2) | 0.0135 (14) | 0.0207 (17) | 0.0009 (16) |
C20 | 0.0551 (17) | 0.0533 (17) | 0.078 (2) | 0.0048 (14) | 0.0265 (15) | 0.0083 (15) |
C21 | 0.064 (2) | 0.083 (2) | 0.068 (2) | 0.0249 (18) | 0.0157 (16) | −0.0131 (18) |
C22 | 0.135 (5) | 0.175 (7) | 0.079 (4) | 0.092 (5) | 0.067 (4) | 0.042 (4) |
C23 | 0.082 (4) | 0.139 (6) | 0.136 (6) | 0.021 (4) | 0.008 (4) | −0.082 (5) |
C24 | 0.066 (2) | 0.081 (3) | 0.076 (3) | 0.017 (2) | 0.025 (2) | −0.006 (2) |
C25 | 0.077 (3) | 0.113 (3) | 0.096 (3) | 0.008 (3) | 0.022 (3) | −0.016 (3) |
C26 | 0.120 (5) | 0.159 (6) | 0.166 (7) | 0.040 (5) | 0.000 (5) | −0.018 (6) |
C27 | 0.094 (4) | 0.136 (6) | 0.088 (5) | 0.000 (5) | 0.010 (4) | −0.036 (4) |
C28 | 0.153 (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) |
N1—C1 | 1.389 (3) | C19—H19A | 0.9300 |
N1—C15 | 1.396 (3) | C20—H20A | 0.9300 |
N1—H1A | 0.8600 | C21—C22' | 1.40 (2) |
C1—C6 | 1.378 (4) | C21—C24' | 1.491 (12) |
C1—C2 | 1.390 (4) | C21—C24 | 1.516 (5) |
C2—C3 | 1.369 (4) | C21—C23 | 1.536 (7) |
C2—H2A | 0.9300 | C21—C22 | 1.574 (7) |
C3—C4 | 1.395 (4) | C21—C23' | 1.615 (19) |
C3—H3A | 0.9300 | C22—H22A | 0.9600 |
C4—C5 | 1.382 (4) | C22—H22B | 0.9600 |
C4—C7 | 1.525 (4) | C22—H22C | 0.9600 |
C5—C6 | 1.378 (4) | C23—H23A | 0.9600 |
C5—H5A | 0.9300 | C23—H23B | 0.9600 |
C6—H6A | 0.9300 | C23—H23C | 0.9600 |
C7—C9 | 1.507 (4) | C24—C25 | 1.553 (13) |
C7—C10 | 1.554 (4) | C24—H24A | 0.9700 |
C7—C8 | 1.557 (4) | C24—H24B | 0.9700 |
C8—H8A | 0.9600 | C25—C27 | 1.495 (10) |
C8—H8B | 0.9600 | C25—C28 | 1.500 (11) |
C8—H8C | 0.9600 | C25—C26 | 1.503 (10) |
C9—H9A | 0.9600 | C26—H26A | 0.9600 |
C9—H9B | 0.9600 | C26—H26B | 0.9600 |
C9—H9C | 0.9600 | C26—H26C | 0.9600 |
C10—C11 | 1.562 (5) | C27—H27A | 0.9600 |
C10—H10A | 0.9700 | C27—H27B | 0.9600 |
C10—H10B | 0.9700 | C27—H27C | 0.9600 |
C11—C14 | 1.484 (6) | C28—H28A | 0.9600 |
C11—C12 | 1.498 (6) | C28—H28B | 0.9600 |
C11—C13 | 1.515 (5) | C28—H28C | 0.9600 |
C11—C14' | 1.79 (2) | C22'—H22D | 0.9600 |
C12—H12A | 0.9600 | C22'—H22E | 0.9600 |
C12—H12B | 0.9600 | C22'—H22F | 0.9600 |
C12—H12C | 0.9600 | C23'—H23D | 0.9600 |
C13—H13A | 0.9600 | C23'—H23E | 0.9600 |
C13—H13B | 0.9600 | C23'—H23F | 0.9600 |
C13—H13C | 0.9600 | C24'—C25' | 1.617 (19) |
C14—H14A | 0.9600 | C24'—H24C | 0.9700 |
C14—H14B | 0.9600 | C24'—H24D | 0.9700 |
C14—H14C | 0.9600 | C25'—C28' | 1.534 (19) |
C14'—H14D | 0.9600 | C25'—C27' | 1.55 (2) |
C14'—H14E | 0.9600 | C25'—C26' | 1.583 (18) |
C14'—H14F | 0.9600 | C26'—H26D | 0.9600 |
C15—C16 | 1.379 (4) | C26'—H26E | 0.9600 |
C15—C20 | 1.381 (4) | C26'—H26F | 0.9600 |
C16—C17 | 1.384 (4) | C27'—H27D | 0.9600 |
C16—H16A | 0.9300 | C27'—H27E | 0.9600 |
C17—C18 | 1.375 (4) | C27'—H27F | 0.9600 |
C17—H17A | 0.9300 | C28'—H28D | 0.9600 |
C18—C19 | 1.376 (4) | C28'—H28E | 0.9600 |
C18—C21 | 1.540 (4) | C28'—H28F | 0.9600 |
C19—C20 | 1.375 (4) | ||
C1—N1—C15 | 129.7 (2) | C22'—C21—C24 | 136.8 (9) |
C1—N1—H1A | 115.2 | C24'—C21—C24 | 50.0 (7) |
C15—N1—H1A | 115.2 | C22'—C21—C23 | 51.2 (11) |
C6—C1—N1 | 124.4 (2) | C24'—C21—C23 | 138.5 (7) |
C6—C1—C2 | 117.6 (2) | C24—C21—C23 | 107.8 (4) |
N1—C1—C2 | 117.9 (2) | C22'—C21—C18 | 110.0 (9) |
C3—C2—C1 | 120.8 (3) | C24'—C21—C18 | 113.7 (7) |
C3—C2—H2A | 119.6 | C24—C21—C18 | 112.5 (3) |
C1—C2—H2A | 119.6 | C23—C21—C18 | 107.3 (3) |
C2—C3—C4 | 122.5 (2) | C22'—C21—C22 | 58.8 (11) |
C2—C3—H3A | 118.7 | C24'—C21—C22 | 64.1 (7) |
C4—C3—H3A | 118.7 | C24—C21—C22 | 110.9 (4) |
C5—C4—C3 | 115.6 (2) | C23—C21—C22 | 108.0 (5) |
C5—C4—C7 | 123.9 (2) | C18—C21—C22 | 110.2 (3) |
C3—C4—C7 | 120.5 (2) | C22'—C21—C23' | 95.9 (11) |
C6—C5—C4 | 122.7 (3) | C24'—C21—C23' | 108.8 (11) |
C6—C5—H5A | 118.7 | C24—C21—C23' | 62.6 (9) |
C4—C5—H5A | 118.7 | C23—C21—C23' | 47.7 (8) |
C5—C6—C1 | 120.8 (2) | C18—C21—C23' | 110.5 (7) |
C5—C6—H6A | 119.6 | C22—C21—C23' | 137.5 (7) |
C1—C6—H6A | 119.6 | C21—C22—H22A | 109.5 |
C9—C7—C4 | 112.5 (2) | C21—C22—H22B | 109.5 |
C9—C7—C10 | 115.3 (3) | C21—C22—H22C | 109.5 |
C4—C7—C10 | 112.4 (2) | C21—C23—H23A | 109.5 |
C9—C7—C8 | 105.2 (3) | C21—C23—H23B | 109.5 |
C4—C7—C8 | 107.6 (2) | H23A—C23—H23B | 109.5 |
C10—C7—C8 | 102.8 (3) | C21—C23—H23C | 109.5 |
C7—C8—H8A | 109.5 | H23A—C23—H23C | 109.5 |
C7—C8—H8B | 109.5 | H23B—C23—H23C | 109.5 |
H8A—C8—H8B | 109.5 | C21—C24—C25 | 123.8 (5) |
C7—C8—H8C | 109.5 | C21—C24—H24A | 106.4 |
H8A—C8—H8C | 109.5 | C25—C24—H24A | 106.4 |
H8B—C8—H8C | 109.5 | C21—C24—H24B | 106.4 |
C7—C9—H9A | 109.5 | C25—C24—H24B | 106.4 |
C7—C9—H9B | 109.5 | H24A—C24—H24B | 106.5 |
H9A—C9—H9B | 109.5 | C27—C25—C28 | 108.8 (9) |
C7—C9—H9C | 109.5 | C27—C25—C26 | 111.6 (8) |
H9A—C9—H9C | 109.5 | C28—C25—C26 | 105.9 (9) |
H9B—C9—H9C | 109.5 | C27—C25—C24 | 111.4 (8) |
C7—C10—C11 | 123.2 (3) | C28—C25—C24 | 120.5 (8) |
C7—C10—H10A | 106.5 | C26—C25—C24 | 97.9 (8) |
C11—C10—H10A | 106.5 | C25—C26—H26A | 109.5 |
C7—C10—H10B | 106.5 | C25—C26—H26B | 109.5 |
C11—C10—H10B | 106.5 | H26A—C26—H26B | 109.5 |
H10A—C10—H10B | 106.5 | C25—C26—H26C | 109.5 |
C14—C11—C12 | 114.8 (5) | H26A—C26—H26C | 109.5 |
C14—C11—C13 | 107.3 (4) | H26B—C26—H26C | 109.5 |
C12—C11—C13 | 107.5 (4) | C25—C27—H27A | 109.5 |
C14—C11—C10 | 111.8 (4) | C25—C27—H27B | 109.5 |
C12—C11—C10 | 111.7 (3) | H27A—C27—H27B | 109.5 |
C13—C11—C10 | 102.8 (3) | C25—C27—H27C | 109.5 |
C14—C11—C14' | 38.9 (10) | H27A—C27—H27C | 109.5 |
C12—C11—C14' | 88.8 (13) | H27B—C27—H27C | 109.5 |
C13—C11—C14' | 89.7 (10) | C25—C28—H28A | 109.5 |
C10—C11—C14' | 150.7 (11) | C25—C28—H28B | 109.5 |
C11—C12—H12A | 109.5 | H28A—C28—H28B | 109.5 |
C11—C12—H12B | 109.5 | C25—C28—H28C | 109.5 |
H12A—C12—H12B | 109.5 | H28A—C28—H28C | 109.5 |
C11—C12—H12C | 109.5 | H28B—C28—H28C | 109.5 |
H12A—C12—H12C | 109.5 | C21—C22'—H22D | 109.5 |
H12B—C12—H12C | 109.5 | C21—C22'—H22E | 109.5 |
C11—C13—H13A | 109.5 | H22D—C22'—H22E | 109.5 |
C11—C13—H13B | 109.5 | C21—C22'—H22F | 109.5 |
H13A—C13—H13B | 109.5 | H22D—C22'—H22F | 109.5 |
C11—C13—H13C | 109.5 | H22E—C22'—H22F | 109.5 |
H13A—C13—H13C | 109.5 | C21—C23'—H23D | 109.5 |
H13B—C13—H13C | 109.5 | C21—C23'—H23E | 109.5 |
C11—C14—H14A | 109.5 | C21—C23'—H23F | 109.5 |
C11—C14—H14B | 109.5 | C21—C24'—C25' | 119.2 (14) |
H14A—C14—H14B | 109.5 | C21—C24'—H24C | 107.5 |
C11—C14—H14C | 109.5 | C25'—C24'—H24C | 107.5 |
H14A—C14—H14C | 109.5 | C21—C24'—H24D | 107.5 |
H14B—C14—H14C | 109.5 | C25'—C24'—H24D | 107.5 |
C11—C14'—H14D | 109.5 | H24C—C24'—H24D | 107.0 |
C11—C14'—H14E | 109.5 | C28'—C25'—C27' | 113 (2) |
H14D—C14'—H14E | 109.5 | C28'—C25'—C26' | 99.3 (17) |
C11—C14'—H14F | 109.5 | C27'—C25'—C26' | 103.2 (19) |
H14D—C14'—H14F | 109.5 | C28'—C25'—C24' | 84.2 (13) |
H14E—C14'—H14F | 109.5 | C27'—C25'—C24' | 96.5 (17) |
C16—C15—C20 | 117.3 (3) | C26'—C25'—C24' | 157 (3) |
C16—C15—N1 | 124.3 (2) | C25'—C26'—H26D | 109.5 |
C20—C15—N1 | 118.3 (3) | C25'—C26'—H26E | 109.5 |
C15—C16—C17 | 120.6 (3) | H26D—C26'—H26E | 109.5 |
C15—C16—H16A | 119.7 | C25'—C26'—H26F | 109.5 |
C17—C16—H16A | 119.7 | H26D—C26'—H26F | 109.5 |
C18—C17—C16 | 122.5 (3) | H26E—C26'—H26F | 109.5 |
C18—C17—H17A | 118.8 | C25'—C27'—H27D | 109.5 |
C16—C17—H17A | 118.8 | C25'—C27'—H27E | 109.5 |
C17—C18—C19 | 116.2 (3) | H27D—C27'—H27E | 109.5 |
C17—C18—C21 | 122.9 (3) | C25'—C27'—H27F | 109.5 |
C19—C18—C21 | 121.0 (3) | H27D—C27'—H27F | 109.5 |
C20—C19—C18 | 122.3 (3) | H27E—C27'—H27F | 109.5 |
C20—C19—H19A | 118.9 | C25'—C28'—H28D | 109.5 |
C18—C19—H19A | 118.9 | C25'—C28'—H28E | 109.5 |
C19—C20—C15 | 121.2 (3) | H28D—C28'—H28E | 109.5 |
C19—C20—H20A | 119.4 | C25'—C28'—H28F | 109.5 |
C15—C20—H20A | 119.4 | H28D—C28'—H28F | 109.5 |
C22'—C21—C24' | 116.5 (12) | H28E—C28'—H28F | 109.5 |
C15—N1—C1—C6 | −24.3 (4) | C18—C19—C20—C15 | 1.1 (5) |
C15—N1—C1—C2 | 159.5 (3) | C16—C15—C20—C19 | −1.4 (4) |
C6—C1—C2—C3 | 0.5 (4) | N1—C15—C20—C19 | 175.6 (3) |
N1—C1—C2—C3 | 177.0 (2) | C17—C18—C21—C22' | 68.8 (14) |
C1—C2—C3—C4 | 1.4 (4) | C19—C18—C21—C22' | −111.5 (13) |
C2—C3—C4—C5 | −2.4 (4) | C17—C18—C21—C24' | −63.9 (8) |
C2—C3—C4—C7 | 178.8 (3) | C19—C18—C21—C24' | 115.8 (8) |
C3—C4—C5—C6 | 1.5 (4) | C17—C18—C21—C24 | −118.6 (4) |
C7—C4—C5—C6 | −179.7 (3) | C19—C18—C21—C24 | 61.1 (4) |
C4—C5—C6—C1 | 0.3 (4) | C17—C18—C21—C23 | 123.0 (5) |
N1—C1—C6—C5 | −177.6 (3) | C19—C18—C21—C23 | −57.3 (5) |
C2—C1—C6—C5 | −1.4 (4) | C17—C18—C21—C22 | 5.7 (5) |
C5—C4—C7—C9 | −10.1 (4) | C19—C18—C21—C22 | −174.6 (4) |
C3—C4—C7—C9 | 168.6 (3) | C17—C18—C21—C23' | 173.5 (10) |
C5—C4—C7—C10 | 122.0 (3) | C19—C18—C21—C23' | −6.8 (10) |
C3—C4—C7—C10 | −59.2 (4) | C22'—C21—C24—C25 | −124.4 (19) |
C5—C4—C7—C8 | −125.5 (3) | C24'—C21—C24—C25 | −36.8 (10) |
C3—C4—C7—C8 | 53.2 (4) | C23—C21—C24—C25 | −176.1 (6) |
C9—C7—C10—C11 | 68.5 (4) | C18—C21—C24—C25 | 65.9 (7) |
C4—C7—C10—C11 | −62.2 (4) | C22—C21—C24—C25 | −58.1 (7) |
C8—C7—C10—C11 | −177.7 (3) | C23'—C21—C24—C25 | 168.1 (10) |
C7—C10—C11—C14 | −62.9 (5) | C21—C24—C25—C27 | −66.0 (9) |
C7—C10—C11—C12 | 67.3 (5) | C21—C24—C25—C28 | 63.2 (10) |
C7—C10—C11—C13 | −177.7 (3) | C21—C24—C25—C26 | 177.0 (6) |
C7—C10—C11—C14' | −64 (2) | C22'—C21—C24'—C25' | 161.2 (18) |
C1—N1—C15—C16 | −22.9 (5) | C24—C21—C24'—C25' | 31.0 (15) |
C1—N1—C15—C20 | 160.4 (3) | C23—C21—C24'—C25' | 100.7 (17) |
C20—C15—C16—C17 | 0.8 (4) | C18—C21—C24'—C25' | −69.3 (19) |
N1—C15—C16—C17 | −175.9 (3) | C22—C21—C24'—C25' | −171.2 (19) |
C15—C16—C17—C18 | 0.1 (4) | C23'—C21—C24'—C25' | 54.2 (19) |
C16—C17—C18—C19 | −0.5 (4) | C21—C24'—C25'—C28' | −161.1 (16) |
C16—C17—C18—C21 | 179.3 (3) | C21—C24'—C25'—C27' | 86 (2) |
C17—C18—C19—C20 | −0.1 (5) | C21—C24'—C25'—C26' | −61 (5) |
C21—C18—C19—C20 | −179.8 (3) |
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) |
V (Å3) | 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) |
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 (Å−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, −0.30 |
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
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