4-Fluoro-2-({[(2R)-1-hy­droxy-1,1,3-tri­phenyl­propan-2-yl]imino}­meth­yl)phenol

Sha, F.; Johnson, A.R.

doi:10.1107/S2414314620015801

organic compounds

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ISSN: 2414-3146

Volume 5| Part 12| December 2020| x201580

https://doi.org/10.1107/S2414314620015801

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4-Fluoro-2-({[(2R)-1-hydroxy-1,1,3-triphenylpropan-2-yl]imino}methyl)phenol

Fanrui Sha ^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 W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 November 2020; accepted 2 December 2020; online 11 December 2020)

The title compound, C₂₈H₂₄FNO₂, crystallizes in the orthorhombic space group P2₁2₁2₁. A hydrogen-bonding network between the tertiary alcohol group and the fluoro substituent results in [010] chains in the solid state.

Keywords: crystal structure; Schiff base; tridentate ligand; chiral molecule.

CCDC reference: 1970566

Structure description

We have synthesized a number of chiral imine diols by Schiff-base condensation of the corresponding salicylaldehydes with (S)- or (R)-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 ). We routinely prepare both enantiomers of the ligands, and a number of them were examined by single-crystal X-ray diffraction, including the L-enantiomer of the title compound, in order to compare the structures of the free and bound ligand.

2-Hydroxy-5-fluoro-benzaldehyde 2S-(1,1,3-triphenylpropanol) imine, C₂₈H₂₄FNO₂, crystallizes in the orthorhombic space group P2₁2₁2₁ as shown in Fig. 1. The major structural features of the two enantiomers are similar, as expected. The L-enantiomer structure was collected at 100 K while the D-enantiomer was collected at 293 K. The unit-cell parameters in the current room-temperature structure are slightly larger (average 1.3%), presumably due to the higher temperature of the data collection. The absolute structure parameter of −0.1 (3) has a large uncertainty but the absolute configuration was verified by synthesis and polarimetry.

Figure 1
The asymmetric unit of the title compound with displacement ellipsoids shown at the 50% probability level. Hydrogen atoms besides H1, H2 and H2A have been omitted for clarity.

The compound has the expected imine–phenol structure as opposed to the iminium–phenoxide tautomer seen in derivatives with less steric bulk. The C23–C28 phenol aromatic ring is close to co-planar with atoms O2 [deviation from the ring plane = 0.040 (2) Å], C22 [–0.061 (2) Å], N1 [–0.034 (2) Å] and C2 [–0.039 (2) Å]. These four atoms exhibit less deviation from the plane than the enantiomer. The C22—N1—C2—C1 torsion angle is 110.2 (2)°, which places atom O1 1.555 (2) Å above the plane of the ring. This deviation is 0.166 Å larger than that for the enantiomer at 100 K, although the torsion angle is almost identical.

The bonds between C27—C28, C23—C28 and C23—C24 are long at 1.39–1.41 Å while those between C24—C25, C25—C26 and C26—C27 are shorter at 1.36–1.37 Å. In contrast, the aromatic rings on the benzyl and phenyl substituents have typical C—C bond distances ranging from 1.37–1.39 Å. The aromatic C28—O2 bond at 1.349 (3) Å is substantially shorter than the aliphatic C1—O1 bond [1.439 (3) Å]. This bonding motif has been seen in related structures (Sha et al., 2019).

There is an intramolecular O2—H2⋯N1 hydrogen bond (Table 1) between the salicylaldehyde alcohol group and the imine nitrogen atom, which closes an S(6) ring and a long-range intermolecular hydrogen bond between the tertiary alcohol O1—H1 and the F1 atom of an adjacent molecule as shown in Fig. 2: the H⋯F and O⋯F distances are 2.94 and 3.720 (3) Å, respectively. Weak intermolecular C—H⋯F and C—H⋯O contacts are also observed.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.86	2.583 (3)	147
O1—H1⋯F1ⁱ	0.82	2.94	3.720 (3)	160
C9—H9⋯F1ⁱⁱ	0.93	2.54	3.467 (3)	175
C14—H14⋯O2ⁱⁱⁱ	0.93	2.58	3.369 (3)	142
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Figure 2
A view of the inter- and intramolecular hydrogen-bonding network along the b axis.

Synthesis and crystallization

Preparative details of the material have been reported previously (Sha et al., 2019). Crystals in the form of light-yellow blocks were obtained by slow evaporation from the mixed solvents of hexane/ethyl acetate.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₈H₂₄FNO₂
M_r	425.48
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.0147 (2), 18.8172 (4), 20.4530 (5)
V (Å³)	2314.87 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.29 × 0.27 × 0.23

Data collection
Diffractometer	Rigaku XtaLAB Mini II
Absorption correction	Analytical [CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ); ABSPACK (Rigaku OD, 2017 $[Rigaku OD (2017). SCALE3 ABSPACK. Rigaku Oxford Diffraction, Yarnton, England.]$ )]
T_min, T_max	0.995, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	73250, 5721, 4529
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.098, 1.03
No. of reflections	5721
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15
Absolute structure	Flack x determined using 1550 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.1 (3)
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ) and CrystalMaker (Palmer, 2020 ).

Structural data

CCDC reference: 1970566

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314620015801/hb4369sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620015801/hb4369Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314620015801/hb4369Isup3.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: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009) and CrystalMaker (Palmer, 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

4-Fluoro-2-({[(2R)-1-hydroxy-1,1,3-triphenylpropan-2-yl]imino}methyl)phenol top

Crystal data top

C₂₈H₂₄FNO₂	D_x = 1.221 Mg m⁻³
M_r = 425.48	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 20629 reflections
a = 6.0147 (2) Å	θ = 2.0–22.8°
b = 18.8172 (4) Å	µ = 0.08 mm⁻¹
c = 20.4530 (5) Å	T = 293 K
V = 2314.87 (11) Å³	Block, clear light yellow
Z = 4	0.29 × 0.27 × 0.23 mm
F(000) = 896

Data collection top

Rigaku XtaLAB Mini II diffractometer	5721 independent reflections
Radiation source: fine-focus sealed X-ray tube, Rigaku (Mo) X-ray Source	4529 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 10.0000 pixels mm^-1	θ_max = 28.3°, θ_min = 2.0°
ω scans	h = −8→8
Absorption correction: analytical [CrysAlisPro (Rigaku OD, 2019); ABSPACK (Rigaku OD, 2017)]	k = −25→25
T_min = 0.995, T_max = 0.996	l = −27→27
73250 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)] = 0.045	w = 1/[σ²(F_o²) + (0.0408P)² + 0.2813P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.098	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.14 e Å⁻³
5721 reflections	Δρ_min = −0.15 e Å⁻³
291 parameters	Absolute structure: Flack x determined using 1550 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.1 (3)
Primary atom site location: structure-invariant direct methods

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
F1	0.9178 (3)	0.82714 (9)	0.12710 (9)	0.0962 (6)
O1	0.2298 (2)	0.51725 (9)	0.34826 (8)	0.0552 (4)
H1	0.203611	0.474846	0.343181	0.083*
O2	0.2834 (3)	0.62611 (10)	0.17459 (9)	0.0684 (5)
H2	0.328661	0.596034	0.200364	0.103*
N1	0.5550 (3)	0.56695 (9)	0.25587 (8)	0.0413 (4)
C1	0.4599 (3)	0.52649 (11)	0.36563 (10)	0.0398 (4)
C2	0.6059 (3)	0.51204 (10)	0.30374 (9)	0.0386 (4)
H2A	0.763405	0.515018	0.315703	0.046*
C3	0.5589 (4)	0.43882 (11)	0.27290 (10)	0.0505 (5)
H3A	0.581351	0.402322	0.305740	0.061*
H3B	0.404359	0.436968	0.259445	0.061*
C4	0.7040 (4)	0.42272 (10)	0.21473 (10)	0.0488 (5)
C5	0.6403 (5)	0.44232 (13)	0.15197 (12)	0.0639 (7)
H5	0.505460	0.465438	0.145449	0.077*
C6	0.7771 (7)	0.42755 (14)	0.09884 (13)	0.0835 (10)
H6	0.733148	0.441041	0.057053	0.100*
C7	0.9761 (7)	0.39330 (17)	0.10751 (18)	0.0886 (11)
H7	1.067032	0.383652	0.071824	0.106*
C8	1.0393 (6)	0.37362 (18)	0.1685 (2)	0.0909 (10)
H8	1.173814	0.350153	0.174553	0.109*
C9	0.9049 (5)	0.38825 (15)	0.22170 (14)	0.0712 (7)
H9	0.951195	0.374498	0.263194	0.085*
C10	0.5143 (3)	0.47796 (10)	0.42366 (9)	0.0402 (4)
C11	0.7181 (4)	0.44477 (12)	0.43239 (11)	0.0495 (5)
H11	0.827905	0.449448	0.400675	0.059*
C12	0.7598 (5)	0.40449 (12)	0.48822 (11)	0.0594 (6)
H12	0.896877	0.382316	0.493428	0.071*
C13	0.5999 (5)	0.39739 (13)	0.53549 (12)	0.0657 (7)
H13	0.628493	0.370747	0.572854	0.079*
C14	0.3965 (5)	0.42993 (14)	0.52737 (11)	0.0652 (7)
H14	0.287022	0.424937	0.559155	0.078*
C15	0.3550 (4)	0.46988 (12)	0.47220 (11)	0.0520 (6)
H15	0.217525	0.491873	0.467401	0.062*
C16	0.4910 (4)	0.60386 (11)	0.38657 (10)	0.0450 (5)
C17	0.6909 (5)	0.62610 (12)	0.41351 (12)	0.0576 (6)
H17	0.803348	0.593111	0.420758	0.069*
C18	0.7254 (6)	0.69653 (14)	0.42975 (14)	0.0764 (8)
H18	0.860574	0.710554	0.447662	0.092*
C19	0.5618 (7)	0.74562 (15)	0.41960 (19)	0.0930 (11)
H19	0.584347	0.792885	0.431100	0.112*
C20	0.3641 (7)	0.72472 (17)	0.3923 (2)	0.1065 (13)
H20	0.253617	0.758201	0.384393	0.128*
C21	0.3279 (5)	0.65428 (15)	0.37652 (17)	0.0797 (9)
H21	0.191920	0.640668	0.358886	0.096*
C22	0.6980 (4)	0.61408 (10)	0.24233 (9)	0.0405 (4)
H22	0.837032	0.612055	0.262127	0.049*
C23	0.6501 (4)	0.67165 (10)	0.19634 (10)	0.0415 (5)
C24	0.8092 (4)	0.72373 (12)	0.18420 (11)	0.0534 (6)
H24	0.944724	0.723285	0.206112	0.064*
C25	0.7621 (5)	0.77581 (12)	0.13918 (11)	0.0600 (6)
C26	0.5670 (5)	0.77790 (13)	0.10519 (12)	0.0649 (7)
H26	0.542130	0.813151	0.074170	0.078*
C27	0.4081 (5)	0.72738 (13)	0.11734 (12)	0.0643 (7)
H27	0.274328	0.728610	0.094574	0.077*
C28	0.4451 (4)	0.67427 (11)	0.16341 (11)	0.0494 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1196 (15)	0.0738 (10)	0.0954 (12)	−0.0342 (10)	−0.0053 (12)	0.0365 (9)
O1	0.0371 (8)	0.0709 (10)	0.0577 (9)	−0.0053 (8)	−0.0042 (7)	0.0022 (8)
O2	0.0602 (11)	0.0715 (11)	0.0735 (12)	−0.0102 (9)	−0.0239 (9)	0.0191 (9)
N1	0.0450 (10)	0.0434 (9)	0.0355 (8)	−0.0008 (8)	−0.0026 (7)	0.0031 (7)
C1	0.0344 (10)	0.0472 (11)	0.0379 (10)	−0.0011 (9)	−0.0006 (9)	0.0030 (8)
C2	0.0407 (11)	0.0398 (10)	0.0354 (9)	−0.0013 (8)	0.0003 (9)	0.0055 (8)
C3	0.0633 (15)	0.0433 (11)	0.0447 (11)	−0.0084 (11)	0.0065 (11)	0.0011 (9)
C4	0.0647 (15)	0.0364 (10)	0.0451 (12)	−0.0073 (10)	0.0022 (11)	−0.0033 (8)
C5	0.0920 (19)	0.0495 (12)	0.0503 (14)	0.0007 (14)	0.0024 (14)	0.0016 (11)
C6	0.144 (3)	0.0599 (15)	0.0463 (14)	−0.013 (2)	0.0211 (18)	0.0026 (11)
C7	0.108 (3)	0.0727 (19)	0.085 (2)	−0.018 (2)	0.041 (2)	−0.0203 (17)
C8	0.073 (2)	0.090 (2)	0.109 (3)	0.0033 (18)	0.013 (2)	−0.035 (2)
C9	0.0765 (19)	0.0720 (16)	0.0652 (16)	0.0083 (15)	−0.0036 (15)	−0.0167 (13)
C10	0.0460 (12)	0.0388 (10)	0.0358 (10)	−0.0093 (9)	−0.0003 (9)	0.0010 (8)
C11	0.0504 (13)	0.0506 (11)	0.0476 (12)	−0.0049 (11)	−0.0025 (10)	0.0081 (9)
C12	0.0697 (17)	0.0526 (13)	0.0557 (14)	−0.0031 (12)	−0.0173 (14)	0.0105 (11)
C13	0.099 (2)	0.0578 (14)	0.0406 (12)	−0.0197 (15)	−0.0153 (14)	0.0125 (11)
C14	0.089 (2)	0.0683 (15)	0.0383 (12)	−0.0223 (15)	0.0110 (13)	0.0044 (11)
C15	0.0564 (14)	0.0538 (12)	0.0458 (12)	−0.0077 (11)	0.0086 (11)	−0.0009 (10)
C16	0.0505 (13)	0.0439 (11)	0.0408 (10)	0.0046 (10)	0.0119 (10)	0.0044 (9)
C17	0.0706 (17)	0.0487 (12)	0.0537 (13)	−0.0050 (12)	−0.0038 (12)	−0.0010 (10)
C18	0.098 (2)	0.0607 (15)	0.0702 (17)	−0.0204 (17)	0.0091 (17)	−0.0113 (13)
C19	0.122 (3)	0.0468 (15)	0.110 (3)	−0.0052 (19)	0.050 (2)	−0.0141 (16)
C20	0.103 (3)	0.0553 (17)	0.162 (4)	0.0271 (19)	0.033 (3)	0.001 (2)
C21	0.0665 (19)	0.0636 (16)	0.109 (2)	0.0174 (15)	0.0101 (17)	−0.0004 (16)
C22	0.0433 (11)	0.0440 (10)	0.0342 (9)	−0.0007 (9)	−0.0013 (9)	0.0033 (8)
C23	0.0537 (13)	0.0385 (10)	0.0323 (9)	0.0028 (9)	0.0016 (9)	0.0003 (8)
C24	0.0629 (15)	0.0514 (12)	0.0458 (12)	−0.0055 (11)	−0.0026 (11)	0.0075 (10)
C25	0.0844 (18)	0.0432 (12)	0.0522 (13)	−0.0071 (12)	0.0050 (14)	0.0087 (10)
C26	0.096 (2)	0.0462 (12)	0.0527 (14)	0.0142 (14)	−0.0048 (15)	0.0117 (10)
C27	0.0745 (18)	0.0602 (14)	0.0581 (14)	0.0113 (14)	−0.0164 (14)	0.0101 (12)
C28	0.0578 (14)	0.0465 (11)	0.0439 (11)	0.0045 (11)	−0.0071 (11)	0.0011 (9)

Geometric parameters (Å, º) top

F1—C25	1.368 (3)	C12—H12	0.9300
O1—H1	0.8200	C12—C13	1.370 (4)
O1—C1	1.439 (3)	C13—H13	0.9300
O2—H2	0.8200	C13—C14	1.378 (4)
O2—C28	1.349 (3)	C14—H14	0.9300
N1—C2	1.456 (2)	C14—C15	1.379 (3)
N1—C22	1.266 (3)	C15—H15	0.9300
C1—C2	1.564 (3)	C16—C17	1.387 (3)
C1—C10	1.533 (3)	C16—C21	1.380 (3)
C1—C16	1.529 (3)	C17—H17	0.9300
C2—H2A	0.9800	C17—C18	1.382 (3)
C2—C3	1.541 (3)	C18—H18	0.9300
C3—H3A	0.9700	C18—C19	1.365 (5)
C3—H3B	0.9700	C19—H19	0.9300
C3—C4	1.506 (3)	C19—C20	1.371 (5)
C4—C5	1.389 (3)	C20—H20	0.9300
C4—C9	1.379 (4)	C20—C21	1.382 (5)
C5—H5	0.9300	C21—H21	0.9300
C5—C6	1.391 (4)	C22—H22	0.9300
C6—H6	0.9300	C22—C23	1.463 (3)
C6—C7	1.371 (5)	C23—C24	1.392 (3)
C7—H7	0.9300	C23—C28	1.406 (3)
C7—C8	1.355 (5)	C24—H24	0.9300
C8—H8	0.9300	C24—C25	1.374 (3)
C8—C9	1.384 (4)	C25—C26	1.364 (4)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.387 (3)	C26—C27	1.371 (4)
C10—C15	1.388 (3)	C27—H27	0.9300
C11—H11	0.9300	C27—C28	1.391 (3)
C11—C12	1.393 (3)

C1—O1—H1	109.5	C12—C13—H13	120.2
C28—O2—H2	109.5	C12—C13—C14	119.7 (2)
C22—N1—C2	120.07 (17)	C14—C13—H13	120.2
O1—C1—C2	108.61 (16)	C13—C14—H14	120.0
O1—C1—C10	108.93 (16)	C13—C14—C15	120.1 (2)
O1—C1—C16	107.55 (17)	C15—C14—H14	120.0
C10—C1—C2	113.77 (16)	C10—C15—H15	119.3
C16—C1—C2	108.88 (15)	C14—C15—C10	121.4 (2)
C16—C1—C10	108.92 (16)	C14—C15—H15	119.3
N1—C2—C1	107.61 (15)	C17—C16—C1	120.29 (19)
N1—C2—H2A	109.3	C21—C16—C1	121.7 (2)
N1—C2—C3	108.70 (16)	C21—C16—C17	117.9 (2)
C1—C2—H2A	109.3	C16—C17—H17	119.5
C3—C2—C1	112.55 (16)	C18—C17—C16	121.0 (3)
C3—C2—H2A	109.3	C18—C17—H17	119.5
C2—C3—H3A	108.9	C17—C18—H18	119.9
C2—C3—H3B	108.9	C19—C18—C17	120.3 (3)
H3A—C3—H3B	107.7	C19—C18—H18	119.9
C4—C3—C2	113.37 (18)	C18—C19—H19	120.2
C4—C3—H3A	108.9	C18—C19—C20	119.5 (3)
C4—C3—H3B	108.9	C20—C19—H19	120.2
C5—C4—C3	121.1 (2)	C19—C20—H20	119.8
C9—C4—C3	121.4 (2)	C19—C20—C21	120.5 (3)
C9—C4—C5	117.5 (2)	C21—C20—H20	119.8
C4—C5—H5	119.8	C16—C21—C20	120.9 (3)
C4—C5—C6	120.4 (3)	C16—C21—H21	119.6
C6—C5—H5	119.8	C20—C21—H21	119.6
C5—C6—H6	119.7	N1—C22—H22	119.2
C7—C6—C5	120.6 (3)	N1—C22—C23	121.70 (19)
C7—C6—H6	119.7	C23—C22—H22	119.2
C6—C7—H7	120.2	C24—C23—C22	120.0 (2)
C8—C7—C6	119.5 (3)	C24—C23—C28	119.53 (19)
C8—C7—H7	120.2	C28—C23—C22	120.43 (19)
C7—C8—H8	119.8	C23—C24—H24	120.7
C7—C8—C9	120.4 (3)	C25—C24—C23	118.6 (2)
C9—C8—H8	119.8	C25—C24—H24	120.7
C4—C9—C8	121.6 (3)	F1—C25—C24	118.9 (3)
C4—C9—H9	119.2	C26—C25—F1	118.5 (2)
C8—C9—H9	119.2	C26—C25—C24	122.6 (2)
C11—C10—C1	123.82 (18)	C25—C26—H26	120.4
C11—C10—C15	117.93 (19)	C25—C26—C27	119.2 (2)
C15—C10—C1	118.15 (19)	C27—C26—H26	120.4
C10—C11—H11	119.7	C26—C27—H27	119.7
C10—C11—C12	120.6 (2)	C26—C27—C28	120.6 (2)
C12—C11—H11	119.7	C28—C27—H27	119.7
C11—C12—H12	119.8	O2—C28—C23	121.85 (19)
C13—C12—C11	120.3 (3)	O2—C28—C27	118.8 (2)
C13—C12—H12	119.8	C27—C28—C23	119.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.86	2.583 (3)	147
O1—H1···F1ⁱ	0.82	2.94	3.720 (3)	160
C9—H9···F1ⁱⁱ	0.93	2.54	3.467 (3)	175
C14—H14···O2ⁱⁱⁱ	0.93	2.58	3.369 (3)	142

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+1/2, −y+1, z+1/2.

Acknowledgements

The authors wish to thank Eric W. Reinheimer for technical support.

Funding information

Funding for this research was provided by: Harvey Mudd College.

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