2-({[(2S)-1-Hy­droxy-1,1,3-tri­phenyl­propan-2-yl]imino}­meth­yl)-4,6-bis­(4-methyl­phen­yl)phenol

Show, V.L.; Fok, E.Y.; Johnson, A.R.

doi:10.1107/S241431462001576X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 5| Part 12| December 2020| x201576

https://doi.org/10.1107/S241431462001576X

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2-({[(2S)-1-Hydroxy-1,1,3-triphenylpropan-2-yl]imino}methyl)-4,6-bis(4-methylphenyl)phenol

Veronica L. Show,^a Emily Y. Fok ^a and Adam R. Johnson ^a ^*

^aDepartment of Chemistry, Harvey Mudd College, 301 Platt Blvd., Claremont, CA 91711, USA
^*Correspondence e-mail: adam_johnson@hmc.edu

Edited by J. Simpson, University of Otago, New Zealand (Received 9 November 2020; accepted 1 December 2020; online 4 December 2020)

The title compound, C₄₂H₃₇NO₂, crystallizes in the orthorhombic space group P2₁2₁2₁ with one molecule in the asymmetric unit. 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 absolute structure parameter of 0.1 (7) has a large uncertainty but the absolute configuration 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.

Table 1
Hydrogen-bond geometry (Å, °)

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

Figure 1
The asymmetric unit of the title compound, showing the atom-numbering scheme. The displacement ellipsoids are shown at the 50% probability level. Hydrogen atoms apart from H1 and H2 have been omitted for clarity and intramolecular hydrogen bonds are shown as dashed lines. Figure generated using CrystalMaker (Palmer, 2020

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 column chromatography 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, CHCH_aH_bPh), 3.02 (apparent d, 1H, J = 12.5 Hz, CHCH_aH_bPh), 2.96 (s, 1H, OH), 2.89 (dd, 1H, J = 13.8, 10.2 Hz, CHCH_aH_bPh), 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.

Figure 2
Synthesis of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₄₂H₃₇NO₂
M_r	587.72
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.2554 (3), 11.5721 (4), 31.9214 (10)
V (Å³)	3418.92 (19)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.31 × 0.16 × 0.11

Data collection
Diffractometer	XtaLAB Mini II
Absorption correction	Analytical [CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO.. Rigaku Oxford Diffraction, Yarnton, England.]$ ) and ABSPACK (Rigaku OD, 2017 $[Rigaku OD (2017). SCALE3 ABSPACK. Rigaku Oxford Diffraction, Yarnton, England.]$ )]
T_min, T_max	0.982, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	88879, 6086, 3835
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.112, 1.01
No. of reflections	6086
No. of parameters	410
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.11
Absolute structure	Flack x determined using 1229 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons, et al, 2013 )
Absolute structure parameter	0.1 (7)
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO.. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and CrystalMaker (Palmer, 2020 ).

Structural data

CCDC reference: 2042781

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S241431462001576X/sj4216sup1.cif

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

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: 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).

2-({[(2S)-1-Hydroxy-1,1,3-triphenylpropan-2-yl]imino}methyl)-4,6-bis(4-methylphenyl)phenol top

Crystal data top

C₄₂H₃₇NO₂	D_x = 1.142 Mg m⁻³
M_r = 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

Data collection top

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	R_int = 0.074
Detector resolution: 10.0000 pixels mm^-1	θ_max = 25.1°, θ_min = 2.2°
ω scans	h = −11→11
Absorption correction: analytical [CrysAlisPro (Rigaku OD, 2019) and ABSPACK (Rigaku OD, 2017)]	k = −13→13
T_min = 0.982, T_max = 0.994	l = −38→38
88879 measured reflections

Refinement top

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(F_o²) + (0.0556P)² + 0.0355P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.112	(Δ/σ)_max = 0.001
S = 1.01	Δρ_max = 0.12 e Å⁻³
6086 reflections	Δρ_min = −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

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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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