organic compounds
2-({[(2S)-1-Hydroxy-1,1,3-triphenylpropan-2-yl]imino}methyl)-4,6-bis(4-methylphenyl)phenol
aDepartment of Chemistry, Harvey Mudd College, 301 Platt Blvd., Claremont, CA 91711, USA
*Correspondence e-mail: adam_johnson@hmc.edu
The title compound, C42H37NO2, crystallizes in the orthorhombic P212121 with one molecule in the An intramolecular hydrogen bond orients the phenol hydroxyl group toward the imine nitrogen. The aliphatic alcohol is engaged in a weak intramolecular hydrogen bond with the imine nitrogen.
Keywords: crystal structure; Schiff base; tridentate ligand; chiral.
CCDC reference: 2042781
Structure description
We have synthesized a number of chiral imine diols by Schiff-base condensation of the corresponding salicylaldehydes with (S)-2-amino-1,1,3-triphenylpropanol (Kang et al., 2004; Liu et al., 2004). These compounds serve as ligands for titanium for the asymmetric intramolecular hydroamination of aminoallenes (Sha et al., 2019; Fok et al., 2020). The parameter of 0.1 (7) has a large uncertainty but the was verified by synthesis and polarimetry.
The compound reported here has the expected imine–phenol structure (Fig. 1) as opposed to the iminium–phenoxide tautomer seen in derivatives with less steric bulk. There is an intramolecular O2—H2⋯N1 hydrogen bond, Table 1. The phenol aromatic ring (C23–C28) is essentially co-planar with O2, C22, and N1; O2 is 0.046 (3) Å above the plane, C22 is 0.083 (4) Å above the plane, and N1 is 0.180 (3) Å above the plane. The C22—N1—C2—C1 torsion angle is 136.5 (3)°, and the N1—C2—C1—O1 torsion angle is 60.2 (3)°, and these result in the positioning of C1 and H1 being pointed towards the open space near N1, and a intramolecular O1—H1⋯N1 hydrogen bond. O1 becomes almost coplanar with the phenol ring, only 0.198 (3) Å below the plane.
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Unlike the significant bond alternation seen in related structures (Sha et al., 2019), the bonds within the phenol ring (C23–C28) are all between 1.391 (4) and 1.406 (4) Å. The aromatic rings on the benzyl and phenyl substituents have typical aromatic bond distances ranging from 1.34–1.41 Å. The aromatic C24—O2 bond at 1.354 (4) Å is substantially shorter than the aliphatic C1—O1 bond of 1.435 (4) Å, as seen in related structures.
Synthesis and crystallization
Details of the preparation of the title compound are shown in Fig. 2. 2-Hydroxy-3,5-di-4-(methyl)phenylbenzaldehyde (0.8654 g, 2.86 mmol) and (S)-2-amino-1,1,3-triphenylpropanol (0.8651 g, 2.86 mmol, 1 equiv.) were dissolved in ethanol (50 ml) and heated overnight at reflux. The solvent was removed in vacuo. The crude product was purified by flash to yield an orange solid (1.348 g, 1.52 mmol, 80.1%). X-ray quality crystals were obtained by slow evaporation of a toluene solution. M.p. 107.7–108.4°C. [α]D: −165° (c = 0.006 g ml−1, EtOAc). Analysis calculated for C42H37NO2: C, 85.83; H, 6.34; N, 2.38. Found: C, 85.47; H, 6.43; N, 2.35. 1H NMR (400 MHz, CDCl3): 13.22 (s, 1H, ArOH), 7.72–6.99 (m, 26H, ArH, HC=N), 4.41 (dd, 1H, J = 10.0, 1.6 Hz, CHCHaHbPh), 3.02 (apparent d, 1H, J = 12.5 Hz, CHCHaHbPh), 2.96 (s, 1H, OH), 2.89 (dd, 1H, J = 13.8, 10.2 Hz, CHCHaHbPh), 2.41 (s, 3H, CH3), 2.38 (s, 3H, CH3). 13C NMR (100 MHz, CDCl3): 167.11 (HC=N), 157.34 (4°), 145.66 (4°), 144.20 (4°), 139.06 (4°), 137.42 (4°), 137.23 (4°), 136.76 (4°), 134.67 (4°), 132.07 (4°), 131.95 (CH), 130.03 (4°), 129.88 (CH), 129.64 (CH), 129.34 (CH), 129.18 (CH), 129.10 (CH), 128.64 (CH), 128.56 (CH), 128.51 (CH), 128.37 (CH), 127.18 (CH), 127.06 (CH), 126.53 (CH), 126.20 (CH), 125.97 (CH), 118.74 (4°), 79.84 (4°), 78.97 (CH, chiral center), 37.54 (CH2), 21.37 (CH3), 21.18 (CH3). MS (APCI): m/z 589 [M+H]+. IR (ATR, diamond): (C=N) = 1628 cm−1.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 2042781
https://doi.org/10.1107/S241431462001576X/sj4216sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462001576X/sj4216Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S241431462001576X/sj4216Isup3.cml
Data collection: CrysAlis PRO (Rigaku OD, 2019); cell
CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and CrystalMaker (Palmer, 2020).C42H37NO2 | Dx = 1.142 Mg m−3 |
Mr = 587.72 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 14764 reflections |
a = 9.2554 (3) Å | θ = 1.9–20.8° |
b = 11.5721 (4) Å | µ = 0.07 mm−1 |
c = 31.9214 (10) Å | T = 293 K |
V = 3418.92 (19) Å3 | Block, clear light yellow |
Z = 4 | 0.31 × 0.16 × 0.11 mm |
F(000) = 1248 |
XtaLAB Mini II diffractometer | 6086 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Rigaku (Mo) X-ray Source | 3835 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 25.1°, θmin = 2.2° |
ω scans | h = −11→11 |
Absorption correction: analytical [CrysAlisPro (Rigaku OD, 2019) and ABSPACK (Rigaku OD, 2017)] | k = −13→13 |
Tmin = 0.982, Tmax = 0.994 | l = −38→38 |
88879 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.0556P)2 + 0.0355P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.112 | (Δ/σ)max = 0.001 |
S = 1.01 | Δρmax = 0.12 e Å−3 |
6086 reflections | Δρmin = −0.11 e Å−3 |
410 parameters | Absolute structure: Flack x determined using 1229 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, et al, 2013) |
0 restraints | Absolute structure parameter: 0.1 (7) |
Primary atom site location: dual |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.6294 (3) | 0.4955 (2) | 0.24453 (7) | 0.0653 (7) | |
H1 | 0.689147 | 0.504113 | 0.263236 | 0.098* | |
O2 | 0.7917 (3) | 0.4887 (2) | 0.35057 (7) | 0.0692 (7) | |
H2 | 0.736655 | 0.464313 | 0.332477 | 0.104* | |
N1 | 0.6319 (3) | 0.3457 (2) | 0.31194 (8) | 0.0532 (7) | |
C1 | 0.6062 (4) | 0.3744 (3) | 0.23755 (10) | 0.0517 (9) | |
C2 | 0.5320 (4) | 0.3249 (3) | 0.27742 (9) | 0.0504 (9) | |
H2A | 0.516244 | 0.241633 | 0.274077 | 0.060* | |
C3 | 0.3884 (4) | 0.3847 (3) | 0.28819 (10) | 0.0639 (10) | |
H3A | 0.407654 | 0.463637 | 0.296750 | 0.077* | |
H3B | 0.328159 | 0.387332 | 0.263330 | 0.077* | |
C4 | 0.3080 (4) | 0.3237 (3) | 0.32255 (11) | 0.0556 (9) | |
C5 | 0.3318 (5) | 0.3464 (4) | 0.36421 (12) | 0.0798 (13) | |
H5 | 0.396579 | 0.404315 | 0.371609 | 0.096* | |
C6 | 0.2621 (6) | 0.2855 (5) | 0.39534 (14) | 0.0977 (16) | |
H6 | 0.280074 | 0.303258 | 0.423272 | 0.117* | |
C7 | 0.1695 (6) | 0.2017 (4) | 0.38588 (17) | 0.0970 (16) | |
H7 | 0.124816 | 0.159862 | 0.407115 | 0.116* | |
C8 | 0.1405 (6) | 0.1773 (4) | 0.34539 (19) | 0.1091 (17) | |
H8 | 0.074177 | 0.119804 | 0.338752 | 0.131* | |
C9 | 0.2096 (5) | 0.2380 (4) | 0.31360 (14) | 0.0921 (14) | |
H9 | 0.188961 | 0.220341 | 0.285810 | 0.111* | |
C10 | 0.5138 (4) | 0.3654 (3) | 0.19787 (10) | 0.0543 (9) | |
C11 | 0.4240 (4) | 0.2731 (3) | 0.18940 (11) | 0.0677 (11) | |
H11 | 0.414767 | 0.214442 | 0.209129 | 0.081* | |
C12 | 0.3474 (4) | 0.2657 (4) | 0.15224 (13) | 0.0770 (12) | |
H12 | 0.285473 | 0.203753 | 0.147597 | 0.092* | |
C13 | 0.3629 (5) | 0.3501 (4) | 0.12213 (14) | 0.0828 (13) | |
H13 | 0.309935 | 0.346367 | 0.097415 | 0.099* | |
C14 | 0.4574 (5) | 0.4401 (4) | 0.12889 (13) | 0.0870 (14) | |
H14 | 0.471721 | 0.495095 | 0.108055 | 0.104* | |
C15 | 0.5317 (5) | 0.4495 (4) | 0.16667 (12) | 0.0744 (12) | |
H15 | 0.593370 | 0.511637 | 0.171223 | 0.089* | |
C16 | 0.7499 (4) | 0.3123 (3) | 0.22963 (9) | 0.0522 (9) | |
C17 | 0.8731 (5) | 0.3723 (4) | 0.21882 (12) | 0.0772 (12) | |
H17 | 0.870032 | 0.452549 | 0.217305 | 0.093* | |
C18 | 1.0013 (5) | 0.3154 (5) | 0.21019 (14) | 0.0910 (14) | |
H18 | 1.082786 | 0.357674 | 0.202763 | 0.109* | |
C19 | 1.0091 (5) | 0.1980 (5) | 0.21249 (13) | 0.0831 (13) | |
H19 | 1.095450 | 0.159806 | 0.206974 | 0.100* | |
C20 | 0.8883 (5) | 0.1375 (4) | 0.22298 (12) | 0.0778 (12) | |
H20 | 0.891793 | 0.057265 | 0.224532 | 0.093* | |
C21 | 0.7618 (4) | 0.1940 (4) | 0.23126 (11) | 0.0703 (11) | |
H21 | 0.680645 | 0.150724 | 0.238279 | 0.084* | |
C22 | 0.6586 (4) | 0.2695 (3) | 0.33965 (10) | 0.0550 (9) | |
H22 | 0.620090 | 0.195694 | 0.336849 | 0.066* | |
C23 | 0.7494 (4) | 0.2969 (3) | 0.37590 (10) | 0.0496 (9) | |
C24 | 0.8122 (4) | 0.4061 (3) | 0.38002 (10) | 0.0526 (9) | |
C25 | 0.8931 (4) | 0.4348 (3) | 0.41580 (10) | 0.0500 (9) | |
C26 | 0.9079 (4) | 0.3519 (3) | 0.44648 (10) | 0.0529 (9) | |
H26 | 0.959861 | 0.370856 | 0.470443 | 0.064* | |
C27 | 0.8493 (4) | 0.2410 (3) | 0.44368 (10) | 0.0478 (8) | |
C28 | 0.7703 (4) | 0.2159 (3) | 0.40773 (10) | 0.0541 (9) | |
H28 | 0.730155 | 0.142665 | 0.404804 | 0.065* | |
C29 | 0.8755 (4) | 0.1531 (3) | 0.47686 (10) | 0.0504 (9) | |
C30 | 1.0031 (4) | 0.1530 (3) | 0.49976 (11) | 0.0604 (10) | |
H30 | 1.071466 | 0.210327 | 0.494851 | 0.072* | |
C31 | 1.0305 (4) | 0.0696 (4) | 0.52972 (11) | 0.0683 (11) | |
H31 | 1.116596 | 0.072379 | 0.544695 | 0.082* | |
C32 | 0.9326 (4) | −0.0180 (3) | 0.53792 (11) | 0.0622 (10) | |
C33 | 0.8045 (4) | −0.0174 (3) | 0.51594 (11) | 0.0621 (10) | |
H33 | 0.735757 | −0.074099 | 0.521325 | 0.075* | |
C34 | 0.7762 (4) | 0.0665 (3) | 0.48582 (10) | 0.0591 (10) | |
H34 | 0.688924 | 0.064645 | 0.471381 | 0.071* | |
C35 | 0.9668 (5) | −0.1114 (4) | 0.56979 (13) | 0.0922 (15) | |
H35A | 0.905661 | −0.102056 | 0.593855 | 0.138* | |
H35B | 1.066098 | −0.105268 | 0.578152 | 0.138* | |
H35C | 0.950142 | −0.185964 | 0.557520 | 0.138* | |
C36 | 0.9554 (4) | 0.5526 (3) | 0.42036 (11) | 0.0561 (10) | |
C37 | 1.0498 (4) | 0.5958 (3) | 0.39045 (11) | 0.0650 (10) | |
H37 | 1.074983 | 0.550160 | 0.367610 | 0.078* | |
C38 | 1.1070 (5) | 0.7055 (4) | 0.39409 (13) | 0.0770 (12) | |
H38 | 1.169606 | 0.732566 | 0.373533 | 0.092* | |
C39 | 1.0733 (6) | 0.7756 (4) | 0.42744 (16) | 0.0842 (14) | |
C40 | 0.9821 (6) | 0.7310 (4) | 0.45696 (15) | 0.0924 (14) | |
H40 | 0.958615 | 0.776139 | 0.480080 | 0.111* | |
C41 | 0.9239 (4) | 0.6224 (4) | 0.45388 (12) | 0.0730 (12) | |
H41 | 0.862259 | 0.595760 | 0.474761 | 0.088* | |
C42 | 1.1356 (8) | 0.8968 (4) | 0.43117 (18) | 0.143 (2) | |
H42A | 1.082749 | 0.948409 | 0.413288 | 0.214* | |
H42B | 1.235355 | 0.895979 | 0.422919 | 0.214* | |
H42C | 1.128080 | 0.922631 | 0.459675 | 0.214* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.090 (2) | 0.0512 (15) | 0.0548 (15) | −0.0053 (15) | −0.0084 (14) | −0.0028 (12) |
O2 | 0.092 (2) | 0.0583 (15) | 0.0569 (15) | −0.0119 (14) | −0.0203 (14) | 0.0123 (13) |
N1 | 0.0618 (18) | 0.0565 (18) | 0.0413 (16) | 0.0019 (16) | −0.0026 (15) | 0.0023 (15) |
C1 | 0.066 (2) | 0.045 (2) | 0.044 (2) | −0.001 (2) | −0.0056 (19) | −0.0016 (16) |
C2 | 0.056 (2) | 0.048 (2) | 0.046 (2) | 0.0028 (19) | −0.0033 (18) | 0.0010 (16) |
C3 | 0.071 (3) | 0.068 (2) | 0.053 (2) | 0.012 (2) | −0.007 (2) | 0.0017 (19) |
C4 | 0.055 (2) | 0.059 (2) | 0.053 (2) | 0.010 (2) | −0.0002 (19) | −0.0080 (19) |
C5 | 0.082 (3) | 0.093 (3) | 0.064 (3) | −0.016 (3) | 0.008 (2) | −0.016 (2) |
C6 | 0.104 (4) | 0.123 (4) | 0.066 (3) | −0.014 (4) | 0.024 (3) | −0.006 (3) |
C7 | 0.104 (4) | 0.081 (3) | 0.106 (4) | 0.005 (3) | 0.049 (3) | −0.008 (3) |
C8 | 0.109 (4) | 0.098 (4) | 0.121 (4) | −0.033 (3) | 0.041 (4) | −0.039 (4) |
C9 | 0.088 (3) | 0.111 (4) | 0.077 (3) | −0.018 (3) | 0.012 (3) | −0.034 (3) |
C10 | 0.062 (2) | 0.053 (2) | 0.048 (2) | 0.0072 (19) | −0.0011 (18) | −0.0027 (18) |
C11 | 0.078 (3) | 0.075 (3) | 0.050 (2) | −0.013 (2) | 0.000 (2) | 0.001 (2) |
C12 | 0.077 (3) | 0.097 (3) | 0.057 (2) | −0.011 (3) | 0.001 (2) | −0.020 (3) |
C13 | 0.086 (3) | 0.094 (3) | 0.068 (3) | 0.017 (3) | −0.022 (3) | −0.018 (3) |
C14 | 0.112 (4) | 0.085 (3) | 0.064 (3) | 0.019 (3) | −0.020 (3) | 0.013 (2) |
C15 | 0.090 (3) | 0.068 (3) | 0.065 (2) | 0.000 (2) | −0.017 (2) | 0.008 (2) |
C16 | 0.055 (2) | 0.061 (2) | 0.0408 (19) | −0.007 (2) | −0.0051 (18) | −0.0024 (17) |
C17 | 0.070 (3) | 0.083 (3) | 0.079 (3) | −0.007 (3) | 0.003 (2) | 0.008 (2) |
C18 | 0.059 (3) | 0.115 (5) | 0.099 (4) | −0.016 (3) | 0.008 (3) | 0.001 (3) |
C19 | 0.069 (3) | 0.109 (4) | 0.071 (3) | 0.018 (3) | −0.001 (2) | −0.009 (3) |
C20 | 0.079 (3) | 0.075 (3) | 0.080 (3) | 0.010 (3) | 0.003 (3) | −0.007 (2) |
C21 | 0.062 (3) | 0.066 (3) | 0.083 (3) | 0.000 (2) | 0.009 (2) | −0.001 (2) |
C22 | 0.062 (2) | 0.054 (2) | 0.050 (2) | 0.0008 (19) | −0.0030 (19) | 0.0009 (18) |
C23 | 0.056 (2) | 0.050 (2) | 0.0423 (19) | −0.0015 (18) | −0.0014 (17) | 0.0007 (17) |
C24 | 0.061 (2) | 0.053 (2) | 0.044 (2) | 0.0029 (19) | 0.0006 (18) | 0.0043 (17) |
C25 | 0.055 (2) | 0.053 (2) | 0.0423 (19) | 0.0028 (19) | 0.0005 (18) | −0.0002 (18) |
C26 | 0.055 (2) | 0.061 (2) | 0.0427 (19) | 0.003 (2) | −0.0013 (17) | −0.0024 (18) |
C27 | 0.050 (2) | 0.051 (2) | 0.0432 (19) | 0.0011 (18) | −0.0006 (17) | 0.0037 (16) |
C28 | 0.058 (2) | 0.053 (2) | 0.052 (2) | −0.0032 (19) | −0.0009 (19) | 0.0029 (18) |
C29 | 0.053 (2) | 0.054 (2) | 0.0452 (18) | 0.002 (2) | −0.0029 (19) | 0.0027 (17) |
C30 | 0.058 (2) | 0.068 (3) | 0.055 (2) | −0.005 (2) | −0.0074 (19) | 0.009 (2) |
C31 | 0.067 (3) | 0.080 (3) | 0.058 (2) | 0.002 (2) | −0.016 (2) | 0.008 (2) |
C32 | 0.071 (3) | 0.062 (2) | 0.054 (2) | 0.008 (2) | −0.003 (2) | 0.0097 (19) |
C33 | 0.063 (2) | 0.062 (3) | 0.062 (2) | −0.003 (2) | 0.000 (2) | 0.014 (2) |
C34 | 0.058 (2) | 0.062 (2) | 0.058 (2) | −0.001 (2) | −0.0077 (19) | 0.007 (2) |
C35 | 0.108 (4) | 0.088 (3) | 0.080 (3) | 0.011 (3) | −0.016 (3) | 0.032 (2) |
C36 | 0.069 (3) | 0.051 (2) | 0.048 (2) | 0.001 (2) | −0.005 (2) | 0.0026 (18) |
C37 | 0.090 (3) | 0.057 (2) | 0.049 (2) | −0.009 (2) | −0.005 (2) | −0.0032 (19) |
C38 | 0.099 (3) | 0.068 (3) | 0.064 (3) | −0.015 (3) | −0.009 (2) | 0.010 (2) |
C39 | 0.112 (4) | 0.052 (3) | 0.089 (3) | −0.014 (3) | −0.015 (3) | 0.002 (3) |
C40 | 0.126 (4) | 0.062 (3) | 0.089 (3) | −0.001 (3) | 0.002 (3) | −0.026 (3) |
C41 | 0.088 (3) | 0.063 (3) | 0.068 (3) | 0.000 (2) | 0.009 (2) | −0.013 (2) |
C42 | 0.214 (7) | 0.064 (3) | 0.149 (5) | −0.046 (4) | −0.014 (5) | −0.014 (3) |
O1—H1 | 0.8200 | C20—H20 | 0.9300 |
O1—C1 | 1.435 (4) | C20—C21 | 1.367 (5) |
O2—H2 | 0.8200 | C21—H21 | 0.9300 |
O2—C24 | 1.354 (4) | C22—H22 | 0.9300 |
N1—C2 | 1.459 (4) | C22—C23 | 1.465 (4) |
N1—C22 | 1.273 (4) | C23—C24 | 1.397 (4) |
C1—C2 | 1.556 (4) | C23—C28 | 1.396 (4) |
C1—C10 | 1.532 (5) | C24—C25 | 1.406 (4) |
C1—C16 | 1.533 (5) | C25—C26 | 1.378 (4) |
C2—H2A | 0.9800 | C25—C36 | 1.487 (5) |
C2—C3 | 1.538 (5) | C26—H26 | 0.9300 |
C3—H3A | 0.9700 | C26—C27 | 1.396 (4) |
C3—H3B | 0.9700 | C27—C28 | 1.391 (4) |
C3—C4 | 1.501 (5) | C27—C29 | 1.488 (4) |
C4—C5 | 1.373 (5) | C28—H28 | 0.9300 |
C4—C9 | 1.377 (5) | C29—C30 | 1.388 (4) |
C5—H5 | 0.9300 | C29—C34 | 1.390 (4) |
C5—C6 | 1.378 (5) | C30—H30 | 0.9300 |
C6—H6 | 0.9300 | C30—C31 | 1.382 (5) |
C6—C7 | 1.329 (6) | C31—H31 | 0.9300 |
C7—H7 | 0.9300 | C31—C32 | 1.385 (5) |
C7—C8 | 1.350 (6) | C32—C33 | 1.378 (5) |
C8—H8 | 0.9300 | C32—C35 | 1.518 (5) |
C8—C9 | 1.389 (6) | C33—H33 | 0.9300 |
C9—H9 | 0.9300 | C33—C34 | 1.392 (5) |
C10—C11 | 1.379 (5) | C34—H34 | 0.9300 |
C10—C15 | 1.402 (5) | C35—H35A | 0.9600 |
C11—H11 | 0.9300 | C35—H35B | 0.9600 |
C11—C12 | 1.385 (5) | C35—H35C | 0.9600 |
C12—H12 | 0.9300 | C36—C37 | 1.388 (5) |
C12—C13 | 1.378 (5) | C36—C41 | 1.372 (5) |
C13—H13 | 0.9300 | C37—H37 | 0.9300 |
C13—C14 | 1.377 (6) | C37—C38 | 1.380 (5) |
C14—H14 | 0.9300 | C38—H38 | 0.9300 |
C14—C15 | 1.392 (5) | C38—C39 | 1.374 (6) |
C15—H15 | 0.9300 | C39—C40 | 1.366 (6) |
C16—C17 | 1.380 (5) | C39—C42 | 1.521 (6) |
C16—C21 | 1.374 (5) | C40—H40 | 0.9300 |
C17—H17 | 0.9300 | C40—C41 | 1.371 (5) |
C17—C18 | 1.385 (6) | C41—H41 | 0.9300 |
C18—H18 | 0.9300 | C42—H42A | 0.9600 |
C18—C19 | 1.363 (6) | C42—H42B | 0.9600 |
C19—H19 | 0.9300 | C42—H42C | 0.9600 |
C19—C20 | 1.361 (6) | ||
C1—O1—H1 | 109.5 | C16—C21—H21 | 118.7 |
C24—O2—H2 | 109.5 | C20—C21—C16 | 122.6 (4) |
C22—N1—C2 | 122.3 (3) | C20—C21—H21 | 118.7 |
O1—C1—C2 | 107.4 (3) | N1—C22—H22 | 119.6 |
O1—C1—C10 | 106.2 (3) | N1—C22—C23 | 120.7 (3) |
O1—C1—C16 | 110.7 (3) | C23—C22—H22 | 119.6 |
C10—C1—C2 | 113.9 (3) | C24—C23—C22 | 120.6 (3) |
C10—C1—C16 | 108.4 (3) | C28—C23—C22 | 120.6 (3) |
C16—C1—C2 | 110.2 (3) | C28—C23—C24 | 118.8 (3) |
N1—C2—C1 | 106.1 (3) | O2—C24—C23 | 121.0 (3) |
N1—C2—H2A | 109.8 | O2—C24—C25 | 118.2 (3) |
N1—C2—C3 | 107.8 (3) | C23—C24—C25 | 120.8 (3) |
C1—C2—H2A | 109.8 | C24—C25—C36 | 120.2 (3) |
C3—C2—C1 | 113.5 (3) | C26—C25—C24 | 117.8 (3) |
C3—C2—H2A | 109.8 | C26—C25—C36 | 122.0 (3) |
C2—C3—H3A | 109.1 | C25—C26—H26 | 118.1 |
C2—C3—H3B | 109.1 | C25—C26—C27 | 123.8 (3) |
H3A—C3—H3B | 107.9 | C27—C26—H26 | 118.1 |
C4—C3—C2 | 112.3 (3) | C26—C27—C29 | 121.3 (3) |
C4—C3—H3A | 109.1 | C28—C27—C26 | 116.7 (3) |
C4—C3—H3B | 109.1 | C28—C27—C29 | 122.0 (3) |
C5—C4—C3 | 122.6 (4) | C23—C28—H28 | 118.9 |
C5—C4—C9 | 116.4 (4) | C27—C28—C23 | 122.2 (3) |
C9—C4—C3 | 121.0 (3) | C27—C28—H28 | 118.9 |
C4—C5—H5 | 119.1 | C30—C29—C27 | 120.9 (3) |
C4—C5—C6 | 121.7 (4) | C30—C29—C34 | 117.0 (3) |
C6—C5—H5 | 119.1 | C34—C29—C27 | 122.1 (3) |
C5—C6—H6 | 119.6 | C29—C30—H30 | 119.3 |
C7—C6—C5 | 120.7 (5) | C31—C30—C29 | 121.4 (4) |
C7—C6—H6 | 119.6 | C31—C30—H30 | 119.3 |
C6—C7—H7 | 120.1 | C30—C31—H31 | 119.3 |
C6—C7—C8 | 119.9 (5) | C30—C31—C32 | 121.5 (3) |
C8—C7—H7 | 120.1 | C32—C31—H31 | 119.3 |
C7—C8—H8 | 119.9 | C31—C32—C35 | 120.8 (4) |
C7—C8—C9 | 120.2 (5) | C33—C32—C31 | 117.6 (3) |
C9—C8—H8 | 119.9 | C33—C32—C35 | 121.6 (4) |
C4—C9—C8 | 121.1 (4) | C32—C33—H33 | 119.4 |
C4—C9—H9 | 119.4 | C32—C33—C34 | 121.2 (4) |
C8—C9—H9 | 119.4 | C34—C33—H33 | 119.4 |
C11—C10—C1 | 123.4 (3) | C29—C34—C33 | 121.4 (3) |
C11—C10—C15 | 118.0 (3) | C29—C34—H34 | 119.3 |
C15—C10—C1 | 118.3 (3) | C33—C34—H34 | 119.3 |
C10—C11—H11 | 119.2 | C32—C35—H35A | 109.5 |
C10—C11—C12 | 121.6 (4) | C32—C35—H35B | 109.5 |
C12—C11—H11 | 119.2 | C32—C35—H35C | 109.5 |
C11—C12—H12 | 120.0 | H35A—C35—H35B | 109.5 |
C13—C12—C11 | 120.0 (4) | H35A—C35—H35C | 109.5 |
C13—C12—H12 | 120.0 | H35B—C35—H35C | 109.5 |
C12—C13—H13 | 120.2 | C37—C36—C25 | 120.5 (3) |
C14—C13—C12 | 119.5 (4) | C41—C36—C25 | 122.3 (3) |
C14—C13—H13 | 120.2 | C41—C36—C37 | 117.3 (4) |
C13—C14—H14 | 119.7 | C36—C37—H37 | 119.5 |
C13—C14—C15 | 120.5 (4) | C38—C37—C36 | 121.0 (4) |
C15—C14—H14 | 119.7 | C38—C37—H37 | 119.5 |
C10—C15—H15 | 119.9 | C37—C38—H38 | 119.3 |
C14—C15—C10 | 120.2 (4) | C39—C38—C37 | 121.4 (4) |
C14—C15—H15 | 119.9 | C39—C38—H38 | 119.3 |
C17—C16—C1 | 121.5 (3) | C38—C39—C42 | 121.3 (5) |
C21—C16—C1 | 122.1 (3) | C40—C39—C38 | 116.8 (4) |
C21—C16—C17 | 116.4 (4) | C40—C39—C42 | 121.9 (5) |
C16—C17—H17 | 119.4 | C39—C40—H40 | 118.7 |
C16—C17—C18 | 121.2 (4) | C39—C40—C41 | 122.7 (4) |
C18—C17—H17 | 119.4 | C41—C40—H40 | 118.7 |
C17—C18—H18 | 119.7 | C36—C41—H41 | 119.6 |
C19—C18—C17 | 120.6 (4) | C40—C41—C36 | 120.8 (4) |
C19—C18—H18 | 119.7 | C40—C41—H41 | 119.6 |
C18—C19—H19 | 120.6 | C39—C42—H42A | 109.5 |
C20—C19—C18 | 118.8 (5) | C39—C42—H42B | 109.5 |
C20—C19—H19 | 120.6 | C39—C42—H42C | 109.5 |
C19—C20—H20 | 119.8 | H42A—C42—H42B | 109.5 |
C19—C20—C21 | 120.3 (4) | H42A—C42—H42C | 109.5 |
C21—C20—H20 | 119.8 | H42B—C42—H42C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N1 | 0.82 | 1.80 | 2.539 (4) | 148 |
O1—H1···N1 | 0.82 | 2.46 | 2.763 (3) | 103 |
Acknowledgements
The authors acknowledge technical assistance from Eric W. Reinheimer.
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