Diethyl (1-benzyl-4-phenyl-3-tri­fluoro­methyl-1H-pyrrol-2-yl)phospho­nate

Jezuita, A.; Cal, D.; Zagórski, P.; Ejsmont, K.; Zarychta, B.

doi:10.1107/S2414314617011221

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 8| August 2017| x171122

https://doi.org/10.1107/S2414314617011221

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Diethyl (1-benzyl-4-phenyl-3-trifluoromethyl-1H-pyrrol-2-yl)phosphonate

Anna Jezuita,^a Dariusz Cal,^b Piotr Zagórski,^b Krzysztof Ejsmont ^a and Bartosz Zarychta ^a ^*

^aFaculty of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland, and ^bDepartment of Organic Chemistry, Faculty of Chemistry, University of Łodz, Tamka 12, 91-403 Łódz, Poland
^*Correspondence e-mail: bzarychta@uni.opole.pl

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 29 July 2017; accepted 30 July 2017; online 8 August 2017)

In the title compound, C₂₂H₂₃F₃NO₃P, the dihedral angles between the pyrrole ring and the benzyl and phenyl rings are 81.38 (7) and 46.21 (8)°, respectively. The ethyl phosphate groups present with P—O—C—C torsion angles of −178.47 (10) and 106.72 (16)°, and an intramolecular C—H⋯O hydrogen bond occurs. In the extended structure, molecules are linked by C—H⋯O and C—H⋯F hydrogen bonds to generate [001] chains.

Keywords: crystal structure; fluorinated heterocycles; phosphonyl group.

CCDC reference: 1565677

Structure description

Heterocycles bearing a trifluoromethyl group have attracted much attention in pharmaceutical sciences as the introduction of fluorine atoms into an organic compound can cause enhancement and modification of their original physical, chemical and biological properties (e.g.: Gouverneur & Muller, 2012 ; Zeng et al., 2014 ). It has been also shown that the presence of a phosphonyl group can influence the biological functions of heterocyclic systems (e.g.: Dang et al., 2009 ; Olszewski & Boduszek, 2010 ). As part of our studies in this area, we now report the crystal structure of the title compound (Fig. 1).

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

The dihedral angles between the pyrrole ring and the benzyl (N-bonded) and phenyl (C-bonded) rings are 81.38 (7) and 46.21 (8)°, respectively. The dihedral angle between the benzyl and phenyl aromatic rings amounts to 50.83 (5)°. The ethyl phosphate groups have different conformations: P1—O3—C1—C2 = −178.47 (10) and P1—O2—C3—C4 = 106.72 (16)°. The molecular structure is stabilized by one intramolecular weak hydrogen bond, i.e.: C16—H16A⋯O1 (Table 1), which generates an S(6) ring.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2	0.97	2.35	3.1144 (16)	135
C8—H8⋯O1ⁱ	0.93	2.43	3.2148 (16)	142
C16—H16B⋯O1ⁱ	0.97	2.43	3.2178 (17)	138
C16—H16B⋯F1ⁱ	0.97	2.45	3.2224 (15)	136
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

In the extended structure, the molecules are linked by C—H⋯O and C—H⋯F hydrogen bonds to generate [001] chains (Fig. 2) in which O1 acts as a double acceptor.

Figure 2
The crystal packing of the title compound, viewed along the a axis showing C8—H8⋯O1ⁱ, C16—H16B⋯O1ⁱ and C16—H16B⋯F1ⁱ [symmetry code: (i) x, − y + $[{1\over 2}]$ , z + $[{1\over 2}]$ ] intermolecular hydrogen bonds.

Synthesis and crystallization

The title compound was synthesized according to a procedure published previously (Cal & Zagórski, 2011 ). Irregular colourless chunks of were recrystallized from a petroleum ether/Et₂O 1:4 solution.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₂₃F₃NO₃P
M_r	437.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	13.7056 (3), 10.6494 (2), 14.9163 (3)
β (°)	91.744 (2)
V (Å³)	2176.12 (8)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.17
Crystal size (mm)	0.27 × 0.20 × 0.15

Data collection
Diffractometer	Oxford Diffraction Xcalibur
No. of measured, independent and observed [I > 2σ(I)] reflections	14420, 4254, 3251
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.079, 0.98
No. of reflections	4254
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.31
Computer programs: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD. Oxford Diffraction Ltd, Abingdon, England.]$ ), SHELXS2014 (Sheldrick, 2015 a), SHELXL2014 (Sheldrick, 2015 b) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1565677

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617011221/hb4162sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617011221/hb4162Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617011221/hb4162Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis CCD (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS2014 (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).

Diethyl (1-benzyl-4-phenyl-3-trifluoromethyl-1H-pyrrol-2-yl)phosphonate top

Crystal data top

C₂₂H₂₃F₃NO₃P	F(000) = 912
M_r = 437.38	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.7056 (3) Å	Cell parameters from 14420 reflections
b = 10.6494 (2) Å	θ = 3.0–26.0°
c = 14.9163 (3) Å	µ = 0.17 mm⁻¹
β = 91.744 (2)°	T = 150 K
V = 2176.12 (8) Å³	Irregular, colourless
Z = 4	0.27 × 0.20 × 0.15 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	3251 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm^-1	θ_max = 26.0°, θ_min = 3.0°
ω scan	h = −16→16
14420 measured reflections	k = −13→13
4254 independent reflections	l = −12→18

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) = 0.079	w = 1/[σ²(F_o²) + (0.0481P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
4254 reflections	Δρ_max = 0.32 e Å⁻³
271 parameters	Δρ_min = −0.31 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 atoms with C_Ar—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) for C—H, with C—H₃ = 0.96 Å and U_iso(H) = 1.5U_eq(C) and with C—H₂ = 0.97 and U_iso(H) = 1.2U_eq(C).

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

	x	y	z	U_iso*/U_eq
N1	0.26227 (8)	0.28475 (10)	0.23073 (7)	0.0171 (2)
O1	0.25503 (8)	0.18705 (9)	−0.02572 (6)	0.0291 (3)
O2	0.24039 (8)	0.04337 (9)	0.11152 (6)	0.0278 (2)
O3	0.39528 (7)	0.13043 (9)	0.08712 (6)	0.0263 (2)
P1	0.28542 (3)	0.16327 (3)	0.06738 (2)	0.02047 (10)
F1	0.27999 (7)	0.45000 (8)	−0.02257 (5)	0.0319 (2)
F2	0.18429 (7)	0.58775 (8)	0.02989 (5)	0.0386 (3)
F3	0.12551 (7)	0.41436 (9)	−0.02136 (6)	0.0409 (3)
C1	0.47105 (11)	0.21634 (16)	0.05827 (10)	0.0327 (4)
H1A	0.4640	0.2972	0.0873	0.039*
H1B	0.4656	0.2287	−0.0061	0.039*
C2	0.56792 (12)	0.1603 (2)	0.08338 (12)	0.0469 (5)
H2A	0.6189	0.2155	0.0650	0.070*
H2B	0.5744	0.0806	0.0541	0.070*
H2C	0.5727	0.1486	0.1472	0.070*
C3	0.13611 (13)	0.01934 (17)	0.10071 (12)	0.0457 (5)
H3A	0.1034	0.0943	0.0783	0.055*
H3B	0.1096	−0.0014	0.1584	0.055*
C4	0.11827 (18)	−0.0846 (2)	0.03792 (16)	0.0701 (7)
H4A	0.0493	−0.0993	0.0312	0.105*
H4B	0.1497	−0.1591	0.0607	0.105*
H4C	0.1441	−0.0637	−0.0193	0.105*
C5	0.25575 (10)	0.29234 (12)	0.13827 (8)	0.0172 (3)
C6	0.21315 (10)	0.40874 (12)	0.11826 (8)	0.0170 (3)
C7	0.19250 (9)	0.47038 (13)	0.20012 (8)	0.0173 (3)
C8	0.22526 (10)	0.39073 (13)	0.26700 (9)	0.0188 (3)
H8	0.2225	0.4071	0.3281	0.023*
C9	0.20027 (11)	0.46319 (13)	0.02681 (9)	0.0242 (3)
C10	0.13887 (10)	0.58735 (13)	0.21848 (9)	0.0200 (3)
C11	0.05005 (11)	0.61462 (14)	0.17435 (10)	0.0267 (3)
H11	0.0274	0.5630	0.1279	0.032*
C12	−0.00447 (12)	0.71717 (15)	0.19877 (12)	0.0363 (4)
H12	−0.0633	0.7345	0.1686	0.044*
C13	0.02780 (14)	0.79382 (17)	0.26762 (12)	0.0437 (5)
H13	−0.0096	0.8622	0.2846	0.052*
C14	0.11546 (14)	0.76936 (16)	0.31135 (12)	0.0433 (5)
H14	0.1376	0.8219	0.3574	0.052*
C15	0.17114 (12)	0.66642 (15)	0.28696 (10)	0.0310 (4)
H15	0.2304	0.6505	0.3168	0.037*
C16	0.30577 (10)	0.18449 (13)	0.28608 (9)	0.0196 (3)
H16A	0.2948	0.1048	0.2559	0.023*
H16B	0.2726	0.1813	0.3426	0.023*
C17	0.41387 (10)	0.19995 (13)	0.30541 (8)	0.0197 (3)
C18	0.46153 (11)	0.31409 (14)	0.29963 (9)	0.0251 (3)
H18	0.4272	0.3847	0.2800	0.030*
C19	0.56011 (12)	0.32431 (15)	0.32285 (10)	0.0315 (4)
H19	0.5913	0.4016	0.3187	0.038*
C20	0.61174 (12)	0.22048 (17)	0.35194 (10)	0.0339 (4)
H20	0.6778	0.2273	0.3673	0.041*
C21	0.56512 (12)	0.10625 (16)	0.35826 (11)	0.0343 (4)
H21	0.5998	0.0360	0.3781	0.041*
C22	0.46686 (11)	0.09576 (14)	0.33519 (10)	0.0271 (3)
H22	0.4360	0.0184	0.3396	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0182 (6)	0.0208 (6)	0.0122 (5)	0.0017 (5)	−0.0011 (4)	0.0016 (5)
O1	0.0432 (7)	0.0281 (6)	0.0156 (5)	0.0017 (5)	−0.0035 (4)	−0.0029 (4)
O2	0.0356 (6)	0.0217 (5)	0.0259 (5)	−0.0050 (5)	−0.0030 (5)	0.0010 (4)
O3	0.0274 (6)	0.0254 (6)	0.0262 (5)	0.0054 (4)	0.0026 (4)	−0.0006 (4)
P1	0.0273 (2)	0.01945 (19)	0.01456 (18)	0.00111 (16)	−0.00119 (14)	−0.00163 (14)
F1	0.0448 (6)	0.0329 (5)	0.0183 (4)	−0.0001 (4)	0.0085 (4)	0.0028 (4)
F2	0.0683 (7)	0.0245 (5)	0.0230 (4)	0.0135 (5)	0.0022 (4)	0.0064 (4)
F3	0.0426 (6)	0.0514 (6)	0.0273 (5)	−0.0019 (5)	−0.0215 (4)	0.0024 (4)
C1	0.0307 (9)	0.0403 (10)	0.0272 (8)	−0.0023 (7)	0.0034 (7)	0.0030 (7)
C2	0.0302 (10)	0.0725 (14)	0.0380 (10)	0.0048 (9)	0.0000 (8)	0.0055 (9)
C3	0.0437 (11)	0.0435 (11)	0.0497 (11)	−0.0130 (9)	−0.0002 (9)	0.0068 (9)
C4	0.0680 (16)	0.0592 (14)	0.0819 (16)	−0.0233 (12)	−0.0168 (13)	−0.0115 (12)
C5	0.0163 (7)	0.0221 (7)	0.0130 (6)	−0.0012 (6)	−0.0021 (5)	0.0003 (5)
C6	0.0155 (7)	0.0196 (7)	0.0158 (6)	−0.0017 (6)	−0.0030 (5)	0.0005 (5)
C7	0.0134 (7)	0.0208 (7)	0.0177 (7)	−0.0010 (6)	−0.0007 (5)	−0.0009 (5)
C8	0.0188 (7)	0.0240 (7)	0.0135 (6)	0.0013 (6)	0.0003 (5)	−0.0024 (5)
C9	0.0326 (9)	0.0226 (8)	0.0172 (7)	0.0032 (7)	−0.0041 (6)	−0.0004 (6)
C10	0.0197 (7)	0.0210 (7)	0.0196 (7)	0.0003 (6)	0.0026 (6)	0.0016 (6)
C11	0.0237 (8)	0.0243 (8)	0.0320 (8)	0.0024 (6)	−0.0024 (6)	−0.0007 (6)
C12	0.0261 (9)	0.0325 (9)	0.0502 (10)	0.0097 (7)	−0.0015 (8)	0.0004 (8)
C13	0.0434 (11)	0.0346 (10)	0.0537 (11)	0.0163 (8)	0.0094 (9)	−0.0074 (8)
C14	0.0542 (12)	0.0363 (10)	0.0393 (10)	0.0084 (9)	−0.0005 (9)	−0.0182 (8)
C15	0.0321 (9)	0.0328 (9)	0.0278 (8)	0.0052 (7)	−0.0044 (7)	−0.0072 (7)
C16	0.0250 (8)	0.0195 (7)	0.0141 (6)	0.0021 (6)	−0.0018 (6)	0.0033 (5)
C17	0.0241 (8)	0.0239 (8)	0.0110 (6)	0.0037 (6)	0.0000 (5)	−0.0019 (5)
C18	0.0268 (8)	0.0247 (8)	0.0235 (7)	0.0026 (6)	−0.0030 (6)	0.0034 (6)
C19	0.0290 (9)	0.0350 (9)	0.0303 (8)	−0.0061 (7)	−0.0024 (7)	0.0000 (7)
C20	0.0222 (8)	0.0503 (11)	0.0290 (9)	0.0055 (8)	−0.0042 (7)	−0.0063 (7)
C21	0.0298 (9)	0.0367 (10)	0.0359 (9)	0.0140 (8)	−0.0064 (7)	−0.0003 (8)
C22	0.0301 (9)	0.0220 (8)	0.0290 (8)	0.0055 (7)	−0.0025 (7)	−0.0008 (6)

Geometric parameters (Å, º) top

N1—C8	1.3567 (17)	C7—C10	1.4763 (19)
N1—C5	1.3817 (16)	C8—H8	0.9300
N1—C16	1.4654 (16)	C10—C15	1.386 (2)
O1—P1	1.4598 (10)	C10—C11	1.3966 (19)
O2—C3	1.456 (2)	C11—C12	1.379 (2)
O2—P1	1.5715 (10)	C11—H11	0.9300
O3—C1	1.4586 (18)	C12—C13	1.374 (2)
O3—P1	1.5650 (10)	C12—H12	0.9300
P1—C5	1.7886 (14)	C13—C14	1.374 (2)
F1—C9	1.3436 (17)	C13—H13	0.9300
F2—C9	1.3455 (16)	C14—C15	1.390 (2)
F3—C9	1.3385 (16)	C14—H14	0.9300
C1—C2	1.493 (2)	C15—H15	0.9300
C1—H1A	0.9700	C16—C17	1.5097 (19)
C1—H1B	0.9700	C16—H16A	0.9700
C2—H2A	0.9600	C16—H16B	0.9700
C2—H2B	0.9600	C17—C18	1.384 (2)
C2—H2C	0.9600	C17—C22	1.392 (2)
C3—C4	1.466 (3)	C18—C19	1.389 (2)
C3—H3A	0.9700	C18—H18	0.9300
C3—H3B	0.9700	C19—C20	1.376 (2)
C4—H4A	0.9600	C19—H19	0.9300
C4—H4B	0.9600	C20—C21	1.379 (2)
C4—H4C	0.9600	C20—H20	0.9300
C5—C6	1.3987 (18)	C21—C22	1.384 (2)
C6—C7	1.4223 (18)	C21—H21	0.9300
C6—C9	1.4877 (18)	C22—H22	0.9300
C7—C8	1.3745 (18)

C8—N1—C5	109.62 (11)	F3—C9—F2	106.18 (11)
C8—N1—C16	122.15 (10)	F1—C9—F2	104.94 (11)
C5—N1—C16	128.16 (11)	F3—C9—C6	114.09 (12)
C3—O2—P1	119.54 (10)	F1—C9—C6	112.71 (11)
C1—O3—P1	119.59 (9)	F2—C9—C6	111.58 (11)
O1—P1—O3	117.57 (6)	C15—C10—C11	118.37 (13)
O1—P1—O2	115.80 (6)	C15—C10—C7	120.00 (12)
O3—P1—O2	97.32 (6)	C11—C10—C7	121.31 (12)
O1—P1—C5	111.45 (6)	C12—C11—C10	120.79 (14)
O3—P1—C5	107.17 (6)	C12—C11—H11	119.6
O2—P1—C5	106.11 (6)	C10—C11—H11	119.6
O3—C1—C2	108.10 (13)	C13—C12—C11	120.21 (15)
O3—C1—H1A	110.1	C13—C12—H12	119.9
C2—C1—H1A	110.1	C11—C12—H12	119.9
O3—C1—H1B	110.1	C12—C13—C14	119.93 (16)
C2—C1—H1B	110.1	C12—C13—H13	120.0
H1A—C1—H1B	108.4	C14—C13—H13	120.0
C1—C2—H2A	109.5	C13—C14—C15	120.26 (16)
C1—C2—H2B	109.5	C13—C14—H14	119.9
H2A—C2—H2B	109.5	C15—C14—H14	119.9
C1—C2—H2C	109.5	C10—C15—C14	120.43 (15)
H2A—C2—H2C	109.5	C10—C15—H15	119.8
H2B—C2—H2C	109.5	C14—C15—H15	119.8
O2—C3—C4	110.34 (16)	N1—C16—C17	114.09 (11)
O2—C3—H3A	109.6	N1—C16—H16A	108.7
C4—C3—H3A	109.6	C17—C16—H16A	108.7
O2—C3—H3B	109.6	N1—C16—H16B	108.7
C4—C3—H3B	109.6	C17—C16—H16B	108.7
H3A—C3—H3B	108.1	H16A—C16—H16B	107.6
C3—C4—H4A	109.5	C18—C17—C22	118.52 (14)
C3—C4—H4B	109.5	C18—C17—C16	123.11 (12)
H4A—C4—H4B	109.5	C22—C17—C16	118.27 (13)
C3—C4—H4C	109.5	C17—C18—C19	120.72 (14)
H4A—C4—H4C	109.5	C17—C18—H18	119.6
H4B—C4—H4C	109.5	C19—C18—H18	119.6
N1—C5—C6	106.19 (11)	C20—C19—C18	120.18 (15)
N1—C5—P1	122.43 (10)	C20—C19—H19	119.9
C6—C5—P1	130.99 (10)	C18—C19—H19	119.9
C5—C6—C7	108.57 (11)	C19—C20—C21	119.72 (15)
C5—C6—C9	125.33 (12)	C19—C20—H20	120.1
C7—C6—C9	125.88 (12)	C21—C20—H20	120.1
C8—C7—C6	105.62 (11)	C20—C21—C22	120.24 (15)
C8—C7—C10	122.65 (12)	C20—C21—H21	119.9
C6—C7—C10	131.45 (12)	C22—C21—H21	119.9
N1—C8—C7	109.98 (11)	C21—C22—C17	120.62 (15)
N1—C8—H8	125.0	C21—C22—H22	119.7
C7—C8—H8	125.0	C17—C22—H22	119.7
F3—C9—F1	106.69 (11)

C1—O3—P1—O1	55.83 (12)	C5—C6—C9—F3	77.75 (18)
C1—O3—P1—O2	−179.97 (10)	C7—C6—C9—F3	−108.26 (15)
C1—O3—P1—C5	−70.55 (11)	C5—C6—C9—F1	−44.13 (18)
C3—O2—P1—O1	−46.40 (13)	C7—C6—C9—F1	129.86 (14)
C3—O2—P1—O3	−171.88 (11)	C5—C6—C9—F2	−161.91 (13)
C3—O2—P1—C5	77.82 (12)	C7—C6—C9—F2	12.1 (2)
P1—O3—C1—C2	−178.47 (11)	C8—C7—C10—C15	44.5 (2)
P1—O2—C3—C4	106.72 (16)	C6—C7—C10—C15	−142.47 (15)
C8—N1—C5—C6	0.25 (14)	C8—C7—C10—C11	−128.81 (15)
C16—N1—C5—C6	−176.76 (13)	C6—C7—C10—C11	44.2 (2)
C8—N1—C5—P1	−173.24 (10)	C15—C10—C11—C12	−0.5 (2)
C16—N1—C5—P1	9.75 (19)	C7—C10—C11—C12	173.01 (14)
O1—P1—C5—N1	169.14 (10)	C10—C11—C12—C13	−0.4 (2)
O3—P1—C5—N1	−60.93 (12)	C11—C12—C13—C14	1.0 (3)
O2—P1—C5—N1	42.25 (12)	C12—C13—C14—C15	−0.8 (3)
O1—P1—C5—C6	−2.57 (15)	C11—C10—C15—C14	0.7 (2)
O3—P1—C5—C6	127.36 (13)	C7—C10—C15—C14	−172.85 (14)
O2—P1—C5—C6	−129.45 (13)	C13—C14—C15—C10	−0.1 (3)
N1—C5—C6—C7	−1.00 (15)	C8—N1—C16—C17	−89.45 (15)
P1—C5—C6—C7	171.72 (11)	C5—N1—C16—C17	87.23 (16)
N1—C5—C6—C9	173.87 (12)	N1—C16—C17—C18	21.10 (18)
P1—C5—C6—C9	−13.4 (2)	N1—C16—C17—C22	−162.55 (12)
C5—C6—C7—C8	1.35 (15)	C22—C17—C18—C19	0.1 (2)
C9—C6—C7—C8	−173.48 (13)	C16—C17—C18—C19	176.48 (12)
C5—C6—C7—C10	−172.52 (13)	C17—C18—C19—C20	0.1 (2)
C9—C6—C7—C10	12.7 (2)	C18—C19—C20—C21	−0.2 (2)
C5—N1—C8—C7	0.62 (15)	C19—C20—C21—C22	0.2 (2)
C16—N1—C8—C7	177.85 (12)	C20—C21—C22—C17	0.0 (2)
C6—C7—C8—N1	−1.20 (15)	C18—C17—C22—C21	−0.2 (2)
C10—C7—C8—N1	173.34 (12)	C16—C17—C22—C21	−176.68 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2	0.97	2.35	3.1144 (16)	135
C8—H8···O1ⁱ	0.93	2.43	3.2148 (16)	142
C16—H16B···O1ⁱ	0.97	2.43	3.2178 (17)	138
C16—H16B···F1ⁱ	0.97	2.45	3.2224 (15)	136

Symmetry code: (i) x, −y+1/2, z+1/2.

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