2-[4-(Di­methyl­amino)­phen­yl]-3,3-di­fluoro-3H-naphtho­[1,2-e][1,3,2]oxaza­borinin-2-ium-3-uide

Dziuk, B.; Ośmiałowski, B.; Skotnicka, A.; Ejsmont, K.; Zarychta, B.

doi:10.1107/S2414314617011415

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 8| August 2017| x171141

https://doi.org/10.1107/S2414314617011415

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2-[4-(Dimethylamino)phenyl]-3,3-difluoro-3H-naphtho[1,2-e][1,3,2]oxazaborinin-2-ium-3-uide

Błażej Dziuk,^a Borys Ośmiałowski,^b Agnieszka Skotnicka,^b Krzysztof Ejsmont ^a and Bartosz Zarychta ^a ^*

^aFaculty of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland, and ^bFaculty of Chemical Technology and Engineering, UniVersity of Technology and Life Sciences, Seminaryjna 3, 85-326 Bydgoszcz, Poland
^*Correspondence e-mail: bzarychta@uni.opole.pl

Edited by I. Brito, University of Antofagasta, Chile (Received 26 July 2017; accepted 2 August 2017; online 8 August 2017)

In the title compound, C₁₉H₁₇BF₂N₂O, a twist about the N—C single bond is observed, making the cross conjugation not as efficient as in the case of a planar structure. The borone complex has tetrahedral geometry. In the crystal, molecules are conected by weak C—H⋯F hydrogen bonds.

Keywords: crystal structure; BODIPY dyes; flurophores.

CCDC reference: 1566411

Structure description

The organic fluorophores commonly known as BODIPY dyes are a class of compounds that are characterized by intense fluorescence, high stability and relatively small Stokes shifts. On the other hand, the difluoroborates that are hydroxy Schiff base derivatives are also important flurophores. It is known that benzannulation and the presence of a strong electron-donating group shift the maxima of absorption and emission towards the red part of the spectrum (Fabian & Hartmann, 1980 ). On the other hand, elongation of the molecule by a π-conjugated spacer also gives similar effect. In such a case, the presence of single bonds gives an the opportunity for rotation while the presence of the –CH=CH– moiety introduces the possibility of photoisomerization. The last two features cause the fluorescence to be less intensive than in rigid compounds. The rigidification of the molecular skeleton may be realized by benzannulation, which is seen in the vibrationally resolved absorption spectra (Grabarz et al., 2016 ; Ośmiałowski et al., 2015 ). In any case, the geometry of molecules in their ground state is the most fundamental property that should be considered.

There is one independent molecule in the asymmetric unit of the title compound. Its molecular structure is shown in Fig. 1. In the crystal, there is only one classical intermolecular hydrogen bond (Table 1), which connects molecules into zigzag chains along the [101] direction (see Fig. 2). The chains are connected to each other by weak van der Waals interactions.

Table 1
Hydrogen-bond geometry (Å, °) [The intramolecular H bond does not appear to be mentioned in the text]

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯F1ⁱ	0.93	2.61	3.3138 (13)	133
C17—H17⋯F2	0.93	2.56	3.1938 (13)	125
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

Figure 2
The crystal packing of the title compound, viewed along the c axis.

The geometry of the 4-(dimethylamino)phenyl and naphthalene groups is typical (Allen, 2002 ). The groups are not co-planar, the dihedral angle between them being 55.12 (3)°. A twist about the N1—C12 single bond is observed, making the cross conjugation not as efficient as in the case of a planar structure. The geometry around B1 atom is tetrahedral and exhibits normal bond distances and angles (Lugo & Richards, 2010 ). The B—N distance [1.589 (2) Å] is notably longer than a normal B1—N1 single bond (ca 1.52 Å; Singh et al., 1986 ; Lugo & Richards, 2010), indicating weak bonding, and the B1—O1 bond is slightly shorter [1.460 (2) versus 1.48 Å]. This pattern of bond lengths is contrary to the model of Itoh and co-workers where the B—O bond is shorter and B—N bond is markedly longer (Itoh et al., 1998 ), indicating that the complex adopts a structure close to an enol tautomer.

Synthesis and crystallization

The synthesis of 2-[4-(dimethylamino)phenyl]-3,3-difluoro-3H-naphtho[1,2-e][1,3,2]oxazaborinin-2-ium-3-uide was performed by the condensation of 2-hydroxy-1-naphtaldehyde (1 g) with N,N-dimethyl-p-phenylenediamine (0.79 g) in anhydrous methanol (10 ml) as a solvent by heating the mixture at boiling point for 12 h. The resulting precipitate was re-crystallized from methanol (m.p. 168.9–171.2°C). The resulting Schiff base (0.67 g, 85%) was treated with BF₃ etherate (1 ml) in chloroform (10 ml) and DIEA (1 ml). The reaction mixture was heated at boiling point for 5 h and 5 ml of Na₂CO₃ (saturated) was added to decompose the excess of BF₃ and neutralize HF. The organic layer was separated and the remaining water layer was extracted with three portions of chloroform. The combined chloroform fractions were evaporated to dryness and next under vacuum to remove DIEA. The remaining solid was purified by flash chromatography on SiO₂ with chloroform as eluent. NMR spectra were recorded using CDCl₃ as a solvent. Crystals of good quality (m.p. 208–209.3°C) were obtained by slow evaporation of a CDCl₃ solution in the NMR tube.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₇BF₂N₂O
M_r	338.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.6529 (4), 17.7072 (5), 10.4833 (4)
β (°)	114.106 (4)
V (Å³)	1635.60 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.23 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10886, 3196, 2485
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.080, 0.98
No. of reflections	3196
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20
Computer programs: CrysAlis CCD and CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1566411

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617011415/bx4006sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617011415/bx4006Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617011415/bx4006Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

(I) top

Crystal data top

C₁₉H₁₇BF₂N₂O	F(000) = 704
M_r = 338.15	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.6529 (4) Å	Cell parameters from 10886 reflections
b = 17.7072 (5) Å	θ = 3.3–26.0°
c = 10.4833 (4) Å	µ = 0.10 mm⁻¹
β = 114.106 (4)°	T = 100 K
V = 1635.60 (11) Å³	Irregular, colourless
Z = 4	0.25 × 0.23 × 0.15 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2485 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm^-1	θ_max = 26.0°, θ_min = 3.3°
ω scan	h = −11→11
10886 measured reflections	k = −21→17
3196 independent reflections	l = −12→12

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0519P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
3196 reflections	Δρ_max = 0.18 e Å⁻³
228 parameters	Δρ_min = −0.20 e Å⁻³

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. All H atoms were found in a difference map but set to idealized positions and treated as riding with C_Ar—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) for C—H and with C—H₃ = 0.96 Å and U_iso(H) = 1.5U_eq(C).

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

	x	y	z	U_iso*/U_eq
O1	0.67086 (9)	0.34092 (4)	0.45068 (8)	0.0198 (2)
F1	0.87188 (8)	0.37674 (4)	0.65386 (7)	0.0293 (2)
F2	0.63047 (8)	0.39784 (4)	0.63418 (7)	0.0302 (2)
B1	0.72560 (16)	0.39555 (7)	0.56491 (14)	0.0196 (3)
N1	0.72551 (10)	0.47697 (5)	0.50108 (9)	0.0161 (2)
N2	1.08863 (11)	0.71216 (5)	0.83259 (10)	0.0235 (2)
C1	0.56665 (13)	0.35922 (6)	0.32362 (12)	0.0175 (3)
C2	0.48595 (13)	0.30025 (6)	0.23360 (13)	0.0210 (3)
H2	0.5040	0.2504	0.2635	0.025*
C3	0.38129 (13)	0.31661 (7)	0.10243 (12)	0.0208 (3)
H3	0.3284	0.2773	0.0441	0.025*
C4	0.35069 (13)	0.39207 (6)	0.05228 (12)	0.0180 (3)
C5	0.23941 (13)	0.40864 (7)	−0.08298 (12)	0.0212 (3)
H5	0.1861	0.3694	−0.1413	0.025*
C6	0.20910 (13)	0.48159 (7)	−0.12919 (12)	0.0216 (3)
H6	0.1362	0.4917	−0.2184	0.026*
C7	0.28848 (13)	0.54113 (7)	−0.04138 (12)	0.0199 (3)
H7	0.2682	0.5906	−0.0732	0.024*
C8	0.39571 (12)	0.52711 (6)	0.09082 (12)	0.0177 (3)
H8	0.4461	0.5673	0.1480	0.021*
C9	0.43083 (12)	0.45235 (6)	0.14152 (12)	0.0160 (2)
C10	0.54181 (12)	0.43441 (6)	0.27937 (11)	0.0157 (2)
C11	0.63361 (12)	0.49104 (6)	0.37190 (12)	0.0164 (3)
H11	0.6278	0.5402	0.3388	0.020*
C12	0.82088 (12)	0.53630 (6)	0.58513 (11)	0.0164 (3)
C13	0.89989 (12)	0.58379 (6)	0.53311 (11)	0.0178 (3)
H13	0.8943	0.5761	0.4434	0.021*
C14	0.98708 (13)	0.64254 (6)	0.61356 (12)	0.0193 (3)
H14	1.0391	0.6739	0.5769	0.023*
C15	0.99802 (13)	0.65550 (6)	0.75010 (12)	0.0180 (3)
C16	0.91852 (13)	0.60575 (7)	0.80092 (12)	0.0202 (3)
H16	0.9238	0.6126	0.8907	0.024*
C17	0.83328 (13)	0.54721 (6)	0.72075 (12)	0.0187 (3)
H17	0.7835	0.5146	0.7576	0.022*
C18	1.14248 (15)	0.77096 (7)	0.76815 (13)	0.0293 (3)
H18A	1.2052	0.7490	0.7267	0.044*
H18B	1.2005	0.8071	0.8378	0.044*
H18C	1.0574	0.7958	0.6972	0.044*
C19	1.08519 (15)	0.72867 (7)	0.96778 (13)	0.0299 (3)
H19A	0.9841	0.7429	0.9542	0.045*
H19B	1.1537	0.7694	1.0119	0.045*
H19C	1.1154	0.6846	1.0261	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0213 (4)	0.0160 (4)	0.0181 (4)	0.0008 (3)	0.0041 (4)	0.0012 (3)
F1	0.0289 (4)	0.0209 (4)	0.0242 (4)	0.0021 (3)	−0.0032 (3)	0.0030 (3)
F2	0.0444 (5)	0.0246 (4)	0.0299 (4)	−0.0075 (3)	0.0235 (4)	−0.0028 (3)
B1	0.0229 (7)	0.0162 (7)	0.0172 (7)	−0.0006 (5)	0.0056 (6)	0.0008 (5)
N1	0.0144 (5)	0.0162 (5)	0.0161 (5)	0.0000 (4)	0.0046 (4)	−0.0010 (4)
N2	0.0272 (6)	0.0206 (5)	0.0202 (6)	−0.0052 (4)	0.0069 (5)	−0.0050 (4)
C1	0.0160 (6)	0.0193 (6)	0.0177 (6)	0.0008 (5)	0.0074 (5)	0.0012 (5)
C2	0.0237 (7)	0.0148 (6)	0.0244 (7)	−0.0006 (5)	0.0098 (5)	−0.0009 (5)
C3	0.0202 (6)	0.0193 (6)	0.0223 (6)	−0.0044 (5)	0.0080 (5)	−0.0066 (5)
C4	0.0142 (6)	0.0215 (6)	0.0191 (6)	−0.0017 (5)	0.0074 (5)	−0.0037 (5)
C5	0.0165 (6)	0.0252 (6)	0.0201 (6)	−0.0021 (5)	0.0057 (5)	−0.0068 (5)
C6	0.0163 (6)	0.0300 (7)	0.0158 (6)	0.0036 (5)	0.0038 (5)	−0.0013 (5)
C7	0.0194 (6)	0.0219 (6)	0.0191 (6)	0.0037 (5)	0.0085 (5)	0.0016 (5)
C8	0.0153 (6)	0.0185 (6)	0.0180 (6)	−0.0012 (5)	0.0055 (5)	−0.0026 (5)
C9	0.0131 (6)	0.0195 (6)	0.0169 (6)	−0.0007 (5)	0.0074 (5)	−0.0021 (5)
C10	0.0145 (6)	0.0166 (6)	0.0163 (6)	−0.0004 (5)	0.0067 (5)	−0.0007 (5)
C11	0.0150 (6)	0.0156 (6)	0.0178 (6)	0.0019 (4)	0.0059 (5)	0.0015 (5)
C12	0.0129 (6)	0.0157 (6)	0.0173 (6)	0.0019 (4)	0.0029 (5)	−0.0001 (5)
C13	0.0180 (6)	0.0192 (6)	0.0130 (6)	0.0028 (5)	0.0030 (5)	0.0010 (5)
C14	0.0190 (6)	0.0173 (6)	0.0200 (6)	−0.0004 (5)	0.0063 (5)	0.0023 (5)
C15	0.0148 (6)	0.0162 (6)	0.0189 (6)	0.0027 (4)	0.0026 (5)	−0.0011 (5)
C16	0.0175 (6)	0.0259 (7)	0.0170 (6)	0.0022 (5)	0.0068 (5)	−0.0023 (5)
C17	0.0159 (6)	0.0206 (6)	0.0199 (6)	0.0003 (5)	0.0077 (5)	0.0005 (5)
C18	0.0327 (8)	0.0199 (7)	0.0294 (7)	−0.0066 (6)	0.0067 (6)	−0.0041 (5)
C19	0.0323 (8)	0.0283 (7)	0.0269 (7)	−0.0050 (6)	0.0100 (6)	−0.0124 (6)

Geometric parameters (Å, º) top

O1—C1	1.3404 (14)	C7—H7	0.9300
O1—B1	1.4602 (15)	C8—C9	1.4152 (16)
F1—B1	1.3779 (15)	C8—H8	0.9300
F2—B1	1.3846 (15)	C9—C10	1.4396 (15)
B1—N1	1.5892 (16)	C10—C11	1.4246 (15)
N1—C11	1.3045 (14)	C11—H11	0.9300
N1—C12	1.4369 (14)	C12—C13	1.3878 (16)
N2—C15	1.3789 (14)	C12—C17	1.3907 (15)
N2—C18	1.4483 (15)	C13—C14	1.3863 (16)
N2—C19	1.4607 (15)	C13—H13	0.9300
C1—C10	1.3981 (15)	C14—C15	1.4105 (16)
C1—C2	1.4096 (16)	C14—H14	0.9300
C2—C3	1.3641 (17)	C15—C16	1.4081 (16)
C2—H2	0.9300	C16—C17	1.3759 (16)
C3—C4	1.4221 (16)	C16—H16	0.9300
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.4165 (16)	C18—H18A	0.9600
C4—C9	1.4218 (16)	C18—H18B	0.9600
C5—C6	1.3685 (17)	C18—H18C	0.9600
C5—H5	0.9300	C19—H19A	0.9600
C6—C7	1.4036 (16)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C7—C8	1.3718 (16)

C1—O1—B1	121.89 (9)	C8—C9—C10	123.32 (10)
F1—B1—F2	111.59 (10)	C4—C9—C10	118.47 (10)
F1—B1—O1	108.81 (10)	C1—C10—C11	118.02 (10)
F2—B1—O1	110.74 (10)	C1—C10—C9	119.98 (10)
F1—B1—N1	109.17 (10)	C11—C10—C9	121.95 (10)
F2—B1—N1	107.93 (9)	N1—C11—C10	122.86 (10)
O1—B1—N1	108.53 (9)	N1—C11—H11	118.6
C11—N1—C12	119.38 (9)	C10—C11—H11	118.6
C11—N1—B1	119.58 (9)	C13—C12—C17	119.07 (10)
C12—N1—B1	121.00 (9)	C13—C12—N1	121.29 (10)
C15—N2—C18	119.15 (10)	C17—C12—N1	119.64 (10)
C15—N2—C19	119.61 (10)	C14—C13—C12	120.68 (10)
C18—N2—C19	117.60 (9)	C14—C13—H13	119.7
O1—C1—C10	121.15 (10)	C12—C13—H13	119.7
O1—C1—C2	118.13 (10)	C13—C14—C15	120.98 (11)
C10—C1—C2	120.69 (11)	C13—C14—H14	119.5
C3—C2—C1	119.80 (11)	C15—C14—H14	119.5
C3—C2—H2	120.1	N2—C15—C16	121.47 (11)
C1—C2—H2	120.1	N2—C15—C14	121.35 (10)
C2—C3—C4	121.91 (11)	C16—C15—C14	117.11 (10)
C2—C3—H3	119.0	C17—C16—C15	121.51 (11)
C4—C3—H3	119.0	C17—C16—H16	119.2
C5—C4—C9	119.31 (11)	C15—C16—H16	119.2
C5—C4—C3	121.52 (10)	C16—C17—C12	120.63 (11)
C9—C4—C3	119.15 (11)	C16—C17—H17	119.7
C6—C5—C4	120.99 (11)	C12—C17—H17	119.7
C6—C5—H5	119.5	N2—C18—H18A	109.5
C4—C5—H5	119.5	N2—C18—H18B	109.5
C5—C6—C7	119.76 (11)	H18A—C18—H18B	109.5
C5—C6—H6	120.1	N2—C18—H18C	109.5
C7—C6—H6	120.1	H18A—C18—H18C	109.5
C8—C7—C6	120.74 (11)	H18B—C18—H18C	109.5
C8—C7—H7	119.6	N2—C19—H19A	109.5
C6—C7—H7	119.6	N2—C19—H19B	109.5
C7—C8—C9	120.99 (10)	H19A—C19—H19B	109.5
C7—C8—H8	119.5	N2—C19—H19C	109.5
C9—C8—H8	119.5	H19A—C19—H19C	109.5
C8—C9—C4	118.20 (10)	H19B—C19—H19C	109.5

C1—O1—B1—F1	−151.50 (10)	O1—C1—C10—C9	179.02 (10)
C1—O1—B1—F2	85.50 (13)	C2—C1—C10—C9	1.17 (16)
C1—O1—B1—N1	−32.81 (14)	C8—C9—C10—C1	177.88 (10)
F1—B1—N1—C11	143.57 (10)	C4—C9—C10—C1	−1.18 (16)
F2—B1—N1—C11	−94.96 (12)	C8—C9—C10—C11	−4.96 (16)
O1—B1—N1—C11	25.11 (14)	C4—C9—C10—C11	175.99 (10)
F1—B1—N1—C12	−38.90 (14)	C12—N1—C11—C10	176.32 (10)
F2—B1—N1—C12	82.57 (12)	B1—N1—C11—C10	−6.11 (16)
O1—B1—N1—C12	−157.36 (9)	C1—C10—C11—N1	−8.74 (16)
B1—O1—C1—C10	21.42 (16)	C9—C10—C11—N1	174.03 (10)
B1—O1—C1—C2	−160.67 (11)	C11—N1—C12—C13	−44.76 (15)
O1—C1—C2—C3	−178.63 (10)	B1—N1—C12—C13	137.71 (11)
C10—C1—C2—C3	−0.71 (17)	C11—N1—C12—C17	134.44 (11)
C1—C2—C3—C4	0.29 (18)	B1—N1—C12—C17	−43.09 (15)
C2—C3—C4—C5	−178.58 (11)	C17—C12—C13—C14	−1.59 (16)
C2—C3—C4—C9	−0.32 (17)	N1—C12—C13—C14	177.62 (10)
C9—C4—C5—C6	0.60 (17)	C12—C13—C14—C15	0.10 (17)
C3—C4—C5—C6	178.85 (11)	C18—N2—C15—C16	−167.37 (11)
C4—C5—C6—C7	−0.39 (17)	C19—N2—C15—C16	−9.36 (17)
C5—C6—C7—C8	−0.38 (17)	C18—N2—C15—C14	15.88 (16)
C6—C7—C8—C9	0.94 (17)	C19—N2—C15—C14	173.89 (11)
C7—C8—C9—C4	−0.71 (16)	C13—C14—C15—N2	177.72 (10)
C7—C8—C9—C10	−179.77 (11)	C13—C14—C15—C16	0.83 (16)
C5—C4—C9—C8	−0.05 (15)	N2—C15—C16—C17	−177.17 (11)
C3—C4—C9—C8	−178.35 (10)	C14—C15—C16—C17	−0.28 (17)
C5—C4—C9—C10	179.05 (10)	C15—C16—C17—C12	−1.21 (17)
C3—C4—C9—C10	0.76 (15)	C13—C12—C17—C16	2.14 (17)
O1—C1—C10—C11	1.74 (16)	N1—C12—C17—C16	−177.08 (10)
C2—C1—C10—C11	−176.11 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F1ⁱ	0.93	2.61	3.3138 (13)	133
C17—H17···F2	0.93	2.56	3.1938 (13)	125

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

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