Crystal structure determination of two pyridine derivatives: 4-[(E)-2-(4-meth­oxy­phen­yl)ethen­yl]-1-methyl­pyridin-1-ium hexa­fluoro-λ6-phosphane and 4-[(E)-2-[4-(di­methyl­amino)­phen­yl]ethen­yl]-1-phenyl-1λ5-pyridin-1-ylium hexa­fluoro-λ6-phosphane

Mani, J.A.M.; Mercina, M.; Inglebert, S.A.; Narayanan, P.; Joseph, V.; Sagayaraj, P.

doi:10.1107/S2056989019001403

research communications

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 75| Part 2| February 2019| Pages 288-291

https://doi.org/10.1107/S2056989019001403

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Crystal structure determination of two pyridine derivatives: 4-[(E)-2-(4-methoxyphenyl)ethenyl]-1-methylpyridin-1-ium hexafluoro-λ⁶-phosphane and 4-{(E)-2-[4-(dimethylamino)phenyl]ethenyl}-1-phenyl-1λ⁵-pyridin-1-ylium hexafluoro-λ⁶-phosphane

J. Arul Martin Mani,^a M. Mercina,^a S. Antony Inglebert,^a P. Narayanan,^b V. Joseph ^a and P. Sagayaraj ^a ^*

^aDepartment of Physics, Loyola College (Autonomous), Chennai 600 034, India, and ^bDepartment of Physics, A. M. Jain College, Chennai 600 114, India
^*Correspondence e-mail: psagayaraj@hotmail.com

Edited by A. J. Lough, University of Toronto, Canada (Received 2 January 2019; accepted 25 January 2019; online 31 January 2019)

The title molecular salts, C₁₆H₁₆NO⁺·PF₆⁻, (I), and C₂₁H₂₁N₂⁺·PF₆⁻, (II), are pyridine derivatives. In compound (I), the cation comprises a methyl N-substituted pyridine ring and a methoxy-substituted benzene ring connected by a C=C double bond. The F atoms of the PF₆⁻ anion are disordered over two sets of sites with refined occupancy factors of 0.614 (7):0.386 (7). In compound (II), the cation comprises a pyridine ring attached to unsubstituted phenyl ring and a dimethylaniline ring, which are connected by a C=C double bond. The anion is PF₆⁻. In both salts, the cation adopts an E configuration with respect to the C=C bond. The pyridine ring makes a dihedral angle of 9.86 (12)° with the methoxy-substituted benzene ring in compound (I) and 11.2 (3)° with the dimethylamine-substituted benzene ring in compound (II). In compound (I), the crystal packing is stabilized by weak C—H⋯F intermolecular interactions which result in R⁴₃(14) ring motifs, forming molecular sheets running parallel to ( $[\overline{1}]$ 03). These are further stabilized by weak P—F⋯π interactions. In compound (II), the crystal packing is stabilized by C—H⋯F interactions, which result in R⁶₆(40) ring motifs, forming molecular sheets running parallel to (101) and these are further connected by π–π interactions.

Keywords: crystal structure; cation; anion; disorder; pyridine derivatives; hydrogen bonding; halogen bonding; molecular sheets.

CCDC references: 1893497; 971522

1. Chemical context

Stilbene-based compounds are the basic element for a number of biologically active natural and synthetic compounds. These compounds have a wide range of biological activities including anti-inflammatory, anticancer, antiviral, antioxidant and more recently neuroprotective effect (Giacomini et al., 2016 ). Pyridine and its derivatives play an important role in developing anticancer drugs (Ghattas et al., 2017 ) and show antibacterial activities (Chanawanno et al., 2010 ). Pyridine is the parent ring system of a large number of naturally occurring products and important industrial, pharmaceutical and agricultural chemicals. Pyridine derivatives have also shown antichagasic activity against Chagas disease, a parasitic infection caused by Trypanosoma cruzi, a parasite that is widely spread in central and South America (Dorigo et al., 1993 ). The title compounds have been tested for in vitro cytotoxicity and anticancer activity, using VERO and MCF-7 (breast cancer) cell lines, respectively. The cells were maintained in minimal essential medium supplemented with 10% FBS, penicillin (100 U ml⁻¹), and streptomycin (100 microgram ml⁻¹) in a humidified atmosphere of 50 microgram ml⁻¹ CO₂ at 310 K.

2. Structural commentary

The molecular structures of the title pyridine derivatives [C₁₆H₁₆NO⁺. PF₆⁻], (I) and [C₂₁H₂₁N₂⁺. PF₆⁻], (II), are shown in Figs. 1 and 2, respectively. In compound (I), the cation comprises a methyl N-substituted pyridine ring (N1/C10–C14) and a methoxy-substituted phenyl ring (C2–C7) connected by the C8=C9 bond. The F atoms of the PF₆⁻ anion are disordered over two sets of sites with refined occupancy factors of 0.614 (7):0.386 (7). In compound (II), the cation comprises a pyridine ring (N2/C7–C11) attached to an unsubstituted phenyl ring (C1–C6) and a dimethylamine-substituted pheny ring (C14–C19), connected by the C12=C13 bond. A PF₆⁻ anion is also present.

Figure 1
The molecular structure of the title compound (I)

with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. In the anion, dashed bonds indicate the minor disorder component.

Figure 2
The molecular structure of the title compound (II)

with the atom-numbering scheme. Displacement ellipsoids are drawn at 30% probability level.

In both compounds, the cations adopt an E configuration with respect to the C=C bond [C8=C9 = 1.312 (4) Å in compound (I) and C12=C13 = 1.348 (8) Å in compound (II)]. The pyridine ring (N1/C10–C14) makes a dihedral angle of 9.86 (12)° with methoxy-substituted benzene ring (C2–C7) in compound (I) whereas in compound (II) the pyridine ring (N2/C7–C11) makes a dihedral angle of 11.2 (3)° with dimethylamine-substituted benzene ring (C14–C19). The pyridine ring in compound (II) is inclined to the unsubstituted phenyl ring (C1–C6) by 54.9 (3)°. The methoxy group oxygen atom O1 of compound (I) deviates from the benzene ring to which it is attached by 0.0317 (1) Å while the methyl group carbon atom C15 deviates from the benzene ring to which it is attached by 0.022 (3) Å. In compound (II), the methylamine group nitrogen atom (N1) deviates from the benzene ring to which it is attached by 0.017 (5) Å.

In compound (I), the methoxy group is (+) anti-periplanar to the phenyl ring (C2–C7), as is evident from the torsion angle C3—C2—O1—C1 of 178.2 (3)°. In compound II, the methylamine group is (−) anti-periplanar to the phenyl ring (C14–C19), which is evident from the torsion angle C16—C17—N1—C21 of −173.9 (5)°.

3. Supramolecular features

In the crystal packing of compound (I), the molecules are linked via intermolecular C12—H12⋯F3(−2 + x, y, −1 + z), C15—H15A⋯F4(−2 + x, −1 + y, −1 + z) and C15—H15B⋯F2(−1 − x, − $[{1\over 2}]$ + y, z) interactions (Table 1), resulting in $[R_{3}^{4}]$ (14) ring motifs, which form molecular sheets lying parallel to ( $[\overline{1}]$ 03) (Fig. 3). The crystal packing is further stabilized by P1—F4⋯Cg1(−x, $[{1\over 2}]$ + y, −z) halogen-bond (XB) interactions, where Cg1 is the centroid of the pyridine ring (N1/C10–C14).

Table 1
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯F2′ⁱ	0.96	2.51	3.220 (8)	131
C12—H12⋯F3ⁱⁱ	0.93	2.60	3.509 (8)	165
C12—H12⋯F3′ⁱⁱ	0.93	2.53	3.454 (16)	176
C13—H13⋯F5′ⁱⁱⁱ	0.93	2.40	3.270 (9)	156
C15—H15A⋯F4ⁱⁱⁱ	0.96	2.53	3.443 (7)	160
C15—H15B⋯F2^iv	0.96	2.46	3.235 (5)	138
C15—H15B⋯F5′^v	0.96	2.49	3.162 (7)	127
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) x-2, y, z-1; (iii) x-2, y-1, z-1; (iv) $[-x-1, y-{\script{1\over 2}}, -z]$ ; (v) $[-x, y-{\script{1\over 2}}, -z]$ .

Figure 3
The crystal packing of the title compound (I)

, viewed along the a axis, showing C—H⋯F intermolecular interactions, resulting in R⁴₃(14) ring motifs, which form two-dimensional molecular sheets running parallel to ( $[\overline{1}]$ 03). Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

In the crystal packing of compound (II), intramolecular C8—H8⋯F6 and intermolecular C11—H11⋯F5(x, 1 + y, z) and C21—H21B⋯F2( $[{1\over 2}]$ + x, − $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z) interactions (Table 2) result in $[R_{6}^{6}]$ (40) ring motifs and form molecular sheets lying parallel to (101) (Fig. 4). These molecular sheets are cross-linked by C16—H16⋯F4(x, −1 − y, − $[{1\over 2}]$ + z) interactions, resulting in a three-dimensional network. The crystal packing is further stabilized by Cg1⋯Cg3(x, −y, − $[{1\over 2}]$ + z) interactions [centroid–centroid distance = 3.646 (4) Å and interplanar distance = 3.397 (2) Å], where Cg1 is the centroid of the pyridine ring (N2/C7–C11) and Cg3 is the centroid of the phenyl ring (C14–C19).

Table 2
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯F6	0.93	2.59	3.486 (8)	162
C11—H11⋯F5ⁱ	0.93	2.55	3.363 (8)	146
C16—H16⋯F4ⁱⁱ	0.93	2.59	3.289 (7)	132
C21—H21B⋯F2ⁱⁱⁱ	0.96	2.64	3.516 (8)	152
Symmetry codes: (i) x, y+1, z; (ii) $[x, -y-1, z-{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 4
The crystal packing of the title compound (II)

, viewed along the b axis, showing intermolecular C—H⋯F interactions, resulting in $[R_{3}^{4}]$ (14) ring motifs, which form molecular sheets lying parallel to (101). Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

4. Database survey

A search of the Cambridge Structural Database (CSD, V5.39, latest update August 2018; Groom et al., 2016 ) found no entry for a hexafluoro-λ⁶-phosphane with pyridine derivatives. However, the cationic structures of substituted pyridine derivatives were found, for example, r-1,t-3-bis[4-(dimethylamino)phenyl]-c-2,t-4-bis(pyridin-4-yl)cyclobutane (Zhang & Zhuang, 2014 ) and 4′-hydroxy-3′-methoxy-N-methyl4-stilbazofium tosylate hydrate (Zhang et al., 1997 ).

5. Synthesis and crystallization

Compound (I)

A solution of N-phenyl-4-picolinium chloride (250 mg, 1.10 mmol), 4-(dimethylamino) benzaldehyde (363 mg, 2.4 mmol), and piperidine (4 drops) in methanol (20 ml) was heated under reflux for 4 h. The addition of diethyl ether to the deep-red solution yielded a dark precipitate, which was filtered, washed with diethyl ether and dried. This crude chloride salt was metathesized to dimethylamino N-phenyl stilbazolium hexafluoro phosphate (DAPSH) by precipitation from water/aqueous NH₄PF₆. A supersaturated solution of DAPSH was prepared using acetonitrile as solvent and the solution was filtered into the growth vessel for slow evaporation by covering the vessel with a perforated sheet. Good quality greenish crystals of compound (I) was grown in a period of 15–25 days.

Compound (II)

Compound (II) was synthesized by the condensation of 1,4-dimethylpyridinium iodide (2.35 g, 10 mmol), methanol (30 ml) and 4-methoxybenzaldehyde (1.36 g, 10 mmol) in the presence of piperidine (0.2 ml). The total mixture was taken in the round-bottom flask (1000 ml capacity) of a Dean–Stark apparatus and refluxed for 1 d and cooled to room temperature. The product 4-methoxy-N-methyl-4-stilbazolium iodide was filtered and recrystallized from methanol. This product (0.706 g, 2 mmol) was dissolved in 70 ml of millipore water and simultaneously sodium hexafluorophosphate (0.338 g, 2 mmol) was dissolved in 30 ml of millipore water by heating at 343 K. Both the solutions were stirred for 3 h and mixed. 4-Methoxy-N-methylstilbazolium hexafluorophosphate (MMSHP) was formed as a yellowish precipitate. A solution of MMSHP and aqueous acetone was prepared with 14.4 g of MMSHP in 200 ml of acetone–water mixed solvent (5:1) and stirred. The clear solution was collected in the growth vessel after filtering it by using 0.2 micrometer porosity millipore filters and the solvent was allowed to evaporate slowly at room temperature. After three weeks, yellowish crystals of compound (II) were harvested.

6. Refinement

Crystal data, data collection and structure refinement details for compounds (I) and (II) are summarized in Table 3. The positions of the hydrogen atoms were localized from the difference-electron-density maps and their distances were geometrically constrained. The hydrogen atoms bound to the C atoms were treated as riding atoms, with d(C—H) = 0.93 and 0.96 Å for aryl and methyl H atoms, respectively, with U_iso(H)= 1.5U_eq(methyl C) and 1.2U_eq(non-methyl C). The rotation angles for methyl groups were optimized by least squares.

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₅H₁₆NO⁺·PF₆⁻	C₂₁H₂₁N₂⁺·PF₆⁻
M_r	371.26	446.37
Crystal system, space group	Monoclinic, P2₁	Monoclinic, Cc
Temperature (K)	296	296
a, b, c (Å)	6.4320 (2), 9.3645 (3), 13.6070 (5)	19.4596 (14), 10.7416 (8), 11.9654 (9)
β (°)	101.868 (2)	125.864 (2)
V (Å³)	802.06 (5)	2026.9 (3)
Z	2	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	0.24	0.20
Crystal size (mm)	0.35 × 0.30 × 0.30	0.35 × 0.30 × 0.30

Data collection
Diffractometer	Bruker Kappa APEXII CCD	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.921, 0.932	0.933, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	8106, 2867, 2606	13796, 3926, 2895
R_int	0.022	0.024
(sin θ/λ)_max (Å⁻¹)	0.617	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.084, 1.02	0.064, 0.203, 1.07
No. of reflections	2867	3926
No. of parameters	273	255
No. of restraints	140	65
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14	0.49, −0.41
Absolute structure	Flack (1983 ), 1198 Friedel pairs	Flack (1983), 1927 Fridel pairs
Absolute structure parameter	0.08 (11)	0.5 (2)
Computer programs: APEX2 and SAINT (Bruker, 2008), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), and PLATON (Spek, 2009 ).

Supporting information

CCDC references: 1893497; 971522

Crystal structure: contains datablocks I, II, global. DOI: https://doi.org/10.1107/S2056989019001403/lh5891sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019001403/lh5891Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989019001403/lh5891IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019001403/lh5891Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989019001403/lh5891IIsup5.cml

checkCIF report

Computing details top

For both structures, data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

4-[(E)-2-(4-Methoxyphenyl)ethenyl]-1-methylpyridin-1-ium hexafluoro-λ⁶-phosphane (I) top

Crystal data top

C₁₅H₁₆NO⁺·PF₆⁻	F(000) = 380
M_r = 371.26	D_x = 1.537 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2867 reflections
a = 6.4320 (2) Å	θ = 2.7–26.0°
b = 9.3645 (3) Å	µ = 0.24 mm⁻¹
c = 13.6070 (5) Å	T = 296 K
β = 101.868 (2)°	Block, green
V = 802.06 (5) Å³	0.35 × 0.30 × 0.30 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	2867 independent reflections
Radiation source: fine-focus sealed tube	2606 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω & φ scans	θ_max = 26.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→7
T_min = 0.921, T_max = 0.932	k = −9→11
8106 measured reflections	l = −16→16

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0459P)² + 0.106P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.084	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.15 e Å⁻³
2867 reflections	Δρ_min = −0.14 e Å⁻³
273 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
140 restraints	Extinction coefficient: 0.016 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1198 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.08 (11)

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.6868 (5)	0.3750 (4)	0.1233 (2)	0.0795 (9)
H1A	0.7984	0.4199	0.1710	0.119*
H1B	0.7430	0.3396	0.0679	0.119*
H1C	0.6290	0.2971	0.1550	0.119*
C2	0.3506 (4)	0.4329 (3)	0.02002 (19)	0.0562 (6)
C3	0.1982 (4)	0.5355 (3)	−0.0083 (2)	0.0638 (7)
H3	0.2204	0.6270	0.0182	0.077*
C4	0.0127 (4)	0.5051 (3)	−0.07556 (19)	0.0605 (6)
H4	−0.0885	0.5764	−0.0937	0.073*
C5	−0.0260 (4)	0.3690 (3)	−0.11688 (16)	0.0494 (6)
C6	0.1323 (4)	0.2680 (3)	−0.08913 (18)	0.0559 (6)
H6	0.1122	0.1769	−0.1167	0.067*
C7	0.3206 (4)	0.2978 (3)	−0.0214 (2)	0.0579 (7)
H7	0.4246	0.2281	−0.0042	0.069*
C8	−0.2243 (4)	0.3294 (4)	−0.18350 (15)	0.0536 (5)
H8	−0.2377	0.2349	−0.2049	0.064*
C9	−0.3863 (4)	0.4140 (3)	−0.21639 (19)	0.0573 (6)
H9	−0.3690	0.5098	−0.1986	0.069*
C10	−0.5907 (4)	0.3729 (3)	−0.27799 (17)	0.0500 (6)
C11	−0.7440 (4)	0.4771 (3)	−0.3090 (2)	0.0601 (6)
H11	−0.7139	0.5720	−0.2915	0.072*
C12	−0.9364 (5)	0.4417 (3)	−0.3646 (2)	0.0613 (7)
H12	−1.0367	0.5131	−0.3844	0.074*
C13	−0.8419 (5)	0.2036 (3)	−0.3640 (2)	0.0593 (7)
H13	−0.8759	0.1099	−0.3836	0.071*
C14	−0.6466 (5)	0.2330 (3)	−0.3077 (2)	0.0588 (7)
H14	−0.5494	0.1594	−0.2888	0.071*
C15	−1.1961 (4)	0.2735 (4)	−0.4540 (2)	0.0741 (8)
H15A	−1.2061	0.1728	−0.4675	0.111*
H15B	−1.2142	0.3250	−0.5162	0.111*
H15C	−1.3048	0.3012	−0.4189	0.111*
N1	−0.9864 (3)	0.3063 (2)	−0.39178 (14)	0.0543 (6)
O1	0.5245 (3)	0.4760 (2)	0.08788 (15)	0.0736 (6)
P1	0.74137 (10)	0.83995 (8)	0.65677 (4)	0.05309 (18)
F1	0.7553 (11)	0.7695 (5)	0.7626 (3)	0.1143 (17)	0.614 (7)
F2	0.5074 (6)	0.8863 (7)	0.6568 (4)	0.1075 (19)	0.614 (7)
F3	0.6535 (12)	0.6952 (7)	0.6034 (6)	0.0961 (19)	0.614 (7)
F4	0.7210 (13)	0.9108 (6)	0.5533 (3)	0.128 (2)	0.614 (7)
F5	0.9725 (6)	0.7933 (8)	0.6592 (6)	0.125 (2)	0.614 (7)
F6	0.800 (3)	0.9748 (11)	0.7254 (10)	0.109 (4)	0.614 (7)
F1'	0.8909 (17)	0.7393 (7)	0.7289 (7)	0.112 (3)	0.386 (7)
F2'	0.5512 (16)	0.7924 (12)	0.6982 (8)	0.140 (4)	0.386 (7)
F3'	0.705 (2)	0.7182 (14)	0.5738 (8)	0.101 (3)	0.386 (7)
F4'	0.5990 (17)	0.9410 (8)	0.5792 (9)	0.127 (4)	0.386 (7)
F5'	0.9347 (16)	0.8884 (11)	0.6106 (7)	0.120 (3)	0.386 (7)
F6'	0.830 (4)	0.9820 (15)	0.7120 (14)	0.084 (4)	0.386 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0625 (16)	0.083 (3)	0.0841 (18)	−0.0033 (15)	−0.0058 (14)	0.0087 (17)
C2	0.0537 (15)	0.0581 (17)	0.0568 (14)	−0.0038 (12)	0.0116 (11)	0.0032 (12)
C3	0.0628 (16)	0.0509 (17)	0.0749 (16)	−0.0001 (12)	0.0080 (13)	−0.0089 (13)
C4	0.0593 (15)	0.0527 (16)	0.0669 (14)	0.0059 (12)	0.0070 (12)	−0.0023 (13)
C5	0.0503 (12)	0.0519 (17)	0.0473 (10)	−0.0017 (10)	0.0130 (9)	0.0013 (10)
C6	0.0586 (15)	0.0464 (14)	0.0637 (14)	−0.0030 (12)	0.0145 (12)	−0.0061 (12)
C7	0.0516 (14)	0.0518 (18)	0.0697 (15)	0.0023 (10)	0.0114 (11)	0.0056 (12)
C8	0.0580 (12)	0.0529 (15)	0.0515 (11)	0.0006 (13)	0.0147 (10)	0.0023 (13)
C9	0.0562 (14)	0.0503 (15)	0.0651 (13)	−0.0013 (11)	0.0116 (11)	0.0012 (12)
C10	0.0523 (13)	0.0486 (19)	0.0512 (11)	−0.0008 (10)	0.0157 (9)	0.0026 (10)
C11	0.0652 (17)	0.0521 (16)	0.0623 (14)	0.0028 (13)	0.0113 (12)	−0.0033 (13)
C12	0.0594 (16)	0.0594 (19)	0.0648 (15)	0.0099 (13)	0.0123 (13)	0.0080 (13)
C13	0.0645 (16)	0.0513 (17)	0.0620 (14)	−0.0023 (13)	0.0129 (13)	−0.0010 (13)
C14	0.0569 (16)	0.0503 (17)	0.0700 (16)	0.0082 (12)	0.0144 (13)	0.0036 (13)
C15	0.0552 (15)	0.097 (2)	0.0656 (15)	−0.0093 (15)	0.0013 (12)	0.0037 (16)
N1	0.0497 (11)	0.0629 (19)	0.0507 (10)	−0.0013 (9)	0.0112 (8)	0.0030 (9)
O1	0.0622 (11)	0.0680 (14)	0.0816 (12)	−0.0055 (10)	−0.0061 (9)	−0.0044 (11)
P1	0.0518 (3)	0.0467 (3)	0.0587 (3)	0.0013 (3)	0.0066 (2)	−0.0026 (3)
F1	0.172 (5)	0.089 (3)	0.079 (2)	0.006 (3)	0.017 (3)	0.028 (2)
F2	0.0611 (19)	0.140 (4)	0.113 (3)	0.024 (2)	−0.0018 (19)	−0.038 (3)
F3	0.095 (4)	0.068 (3)	0.116 (4)	−0.008 (2)	−0.001 (3)	−0.025 (3)
F4	0.213 (6)	0.109 (4)	0.073 (2)	0.015 (4)	0.057 (3)	0.015 (2)
F5	0.063 (2)	0.139 (5)	0.173 (5)	0.018 (2)	0.019 (3)	−0.057 (4)
F6	0.111 (5)	0.091 (6)	0.121 (6)	0.004 (4)	0.018 (4)	−0.057 (5)
F1'	0.136 (6)	0.074 (4)	0.099 (5)	0.026 (4)	−0.037 (4)	0.005 (4)
F2'	0.115 (6)	0.149 (7)	0.182 (7)	−0.035 (5)	0.092 (5)	−0.004 (6)
F3'	0.116 (7)	0.093 (6)	0.092 (5)	−0.020 (4)	0.018 (4)	−0.039 (4)
F4'	0.127 (6)	0.080 (4)	0.136 (7)	0.007 (4)	−0.064 (5)	0.017 (4)
F5'	0.115 (5)	0.120 (6)	0.146 (6)	−0.027 (4)	0.079 (5)	−0.019 (5)
F6'	0.102 (7)	0.056 (5)	0.091 (5)	−0.021 (5)	0.010 (5)	−0.009 (4)

Geometric parameters (Å, º) top

C1—O1	1.418 (4)	C11—H11	0.9300
C1—H1A	0.9600	C12—N1	1.341 (4)
C1—H1B	0.9600	C12—H12	0.9300
C1—H1C	0.9600	C13—N1	1.338 (3)
C2—O1	1.357 (3)	C13—C14	1.358 (4)
C2—C3	1.370 (4)	C13—H13	0.9300
C2—C7	1.382 (4)	C14—H14	0.9300
C3—C4	1.376 (4)	C15—N1	1.470 (3)
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.395 (4)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.385 (4)	P1—F2'	1.515 (6)
C5—C8	1.452 (3)	P1—F4	1.537 (4)
C6—C7	1.391 (4)	P1—F5	1.543 (4)
C6—H6	0.9300	P1—F1'	1.545 (6)
C7—H7	0.9300	P1—F4'	1.566 (6)
C8—C9	1.312 (4)	P1—F2	1.566 (4)
C8—H8	0.9300	P1—F1	1.570 (4)
C9—C10	1.458 (4)	P1—F6	1.570 (8)
C9—H9	0.9300	P1—F5'	1.571 (6)
C10—C11	1.390 (4)	P1—F6'	1.575 (12)
C10—C14	1.396 (4)	P1—F3	1.586 (6)
C11—C12	1.352 (4)	P1—F3'	1.588 (10)

O1—C1—H1A	109.5	F2'—P1—F1'	91.7 (6)
O1—C1—H1B	109.5	F4—P1—F1'	140.3 (5)
H1A—C1—H1B	109.5	F5—P1—F1'	48.9 (4)
O1—C1—H1C	109.5	F2'—P1—F4'	91.4 (6)
H1A—C1—H1C	109.5	F5—P1—F4'	127.8 (6)
H1B—C1—H1C	109.5	F1'—P1—F4'	176.6 (7)
O1—C2—C3	115.2 (3)	F4—P1—F2	88.8 (3)
O1—C2—C7	125.2 (3)	F5—P1—F2	178.8 (4)
C3—C2—C7	119.7 (2)	F1'—P1—F2	129.9 (5)
C2—C3—C4	121.0 (3)	F4'—P1—F2	53.4 (5)
C2—C3—H3	119.5	F2'—P1—F1	55.5 (5)
C4—C3—H3	119.5	F4—P1—F1	178.2 (4)
C3—C4—C5	121.0 (3)	F5—P1—F1	89.4 (4)
C3—C4—H4	119.5	F4'—P1—F1	142.0 (6)
C5—C4—H4	119.5	F2—P1—F1	89.4 (3)
C6—C5—C4	117.0 (2)	F2'—P1—F6	97.4 (7)
C6—C5—C8	119.9 (2)	F4—P1—F6	99.3 (6)
C4—C5—C8	123.1 (2)	F5—P1—F6	95.9 (7)
C5—C6—C7	122.3 (3)	F1'—P1—F6	94.1 (6)
C5—C6—H6	118.8	F4'—P1—F6	87.2 (7)
C7—C6—H6	118.8	F2—P1—F6	83.7 (6)
C2—C7—C6	118.9 (2)	F1—P1—F6	80.3 (6)
C2—C7—H7	120.5	F2'—P1—F5'	178.3 (5)
C6—C7—H7	120.5	F4—P1—F5'	55.6 (4)
C9—C8—C5	126.3 (3)	F1'—P1—F5'	89.4 (5)
C9—C8—H8	116.8	F4'—P1—F5'	87.5 (6)
C5—C8—H8	116.8	F2—P1—F5'	139.4 (5)
C8—C9—C10	126.5 (3)	F1—P1—F5'	126.0 (5)
C8—C9—H9	116.7	F6—P1—F5'	83.8 (6)
C10—C9—H9	116.7	F2'—P1—F6'	108.1 (9)
C11—C10—C14	116.5 (2)	F4—P1—F6'	91.5 (7)
C11—C10—C9	119.2 (2)	F5—P1—F6'	88.7 (10)
C14—C10—C9	124.2 (2)	F1'—P1—F6'	95.5 (8)
C12—C11—C10	120.5 (3)	F4'—P1—F6'	85.1 (8)
C12—C11—H11	119.7	F2—P1—F6'	91.0 (9)
C10—C11—H11	119.7	F1—P1—F6'	88.3 (7)
N1—C12—C11	121.7 (3)	F5'—P1—F6'	73.1 (9)
N1—C12—H12	119.1	F2'—P1—F3	71.4 (4)
C11—C12—H12	119.1	F4—P1—F3	89.7 (3)
N1—C13—C14	121.5 (3)	F5—P1—F3	91.1 (3)
N1—C13—H13	119.3	F1'—P1—F3	83.5 (4)
C14—C13—H13	119.3	F4'—P1—F3	96.0 (4)
C13—C14—C10	120.4 (3)	F2—P1—F3	89.1 (3)
C13—C14—H14	119.8	F1—P1—F3	90.5 (3)
C10—C14—H14	119.8	F6—P1—F3	168.4 (6)
N1—C15—H15A	109.5	F5'—P1—F3	107.5 (4)
N1—C15—H15B	109.5	F6'—P1—F3	178.8 (8)
H15A—C15—H15B	109.5	F2'—P1—F3'	92.4 (5)
N1—C15—H15C	109.5	F4—P1—F3'	71.7 (5)
H15A—C15—H15C	109.5	F5—P1—F3'	79.2 (5)
H15B—C15—H15C	109.5	F1'—P1—F3'	89.7 (6)
C13—N1—C12	119.3 (2)	F4'—P1—F3'	88.5 (7)
C13—N1—C15	121.0 (3)	F2—P1—F3'	101.4 (5)
C12—N1—C15	119.8 (2)	F1—P1—F3'	108.9 (5)
C2—O1—C1	118.6 (3)	F6—P1—F3'	169.4 (7)
F2'—P1—F4	123.0 (5)	F5'—P1—F3'	86.3 (5)
F2'—P1—F5	139.2 (6)	F6'—P1—F3'	158.7 (9)
F4—P1—F5	92.4 (4)

O1—C2—C3—C4	−179.0 (2)	C8—C9—C10—C14	2.9 (4)
C7—C2—C3—C4	1.8 (4)	C14—C10—C11—C12	0.4 (4)
C2—C3—C4—C5	0.0 (4)	C9—C10—C11—C12	−178.7 (2)
C3—C4—C5—C6	−1.6 (4)	C10—C11—C12—N1	−0.1 (4)
C3—C4—C5—C8	176.3 (2)	N1—C13—C14—C10	−0.6 (4)
C4—C5—C6—C7	1.5 (4)	C11—C10—C14—C13	0.0 (4)
C8—C5—C6—C7	−176.5 (2)	C9—C10—C14—C13	179.0 (2)
O1—C2—C7—C6	179.0 (2)	C14—C13—N1—C12	0.9 (4)
C3—C2—C7—C6	−1.9 (4)	C14—C13—N1—C15	179.1 (3)
C5—C6—C7—C2	0.2 (4)	C11—C12—N1—C13	−0.5 (4)
C6—C5—C8—C9	−179.4 (2)	C11—C12—N1—C15	−178.7 (2)
C4—C5—C8—C9	2.8 (4)	C3—C2—O1—C1	178.2 (3)
C5—C8—C9—C10	−175.8 (2)	C7—C2—O1—C1	−2.7 (4)
C8—C9—C10—C11	−178.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···F2′ⁱ	0.96	2.51	3.220 (8)	131
C12—H12···F3ⁱⁱ	0.93	2.60	3.509 (8)	165
C12—H12···F3′ⁱⁱ	0.93	2.53	3.454 (16)	176
C13—H13···F5′ⁱⁱⁱ	0.93	2.40	3.270 (9)	156
C15—H15A···F4ⁱⁱⁱ	0.96	2.53	3.443 (7)	160
C15—H15B···F2^iv	0.96	2.46	3.235 (5)	138
C15—H15B···F5′^v	0.96	2.49	3.162 (7)	127

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

4-{(E)-2-[4-(Dimethylamino)phenyl]ethenyl}-1-phenyl-1λ⁵-pyridin-\ 1-ylium hexafluoro-λ⁶-phosphane (II) top

Crystal data top

C₂₁H₂₁N₂⁺·PF₆⁻	F(000) = 920
M_r = 446.37	D_x = 1.463 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3926 reflections
a = 19.4596 (14) Å	θ = 2.3–26.0°
b = 10.7416 (8) Å	µ = 0.20 mm⁻¹
c = 11.9654 (9) Å	T = 296 K
β = 125.864 (2)°	Block, yellow
V = 2026.9 (3) Å³	0.35 × 0.30 × 0.30 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3926 independent reflections
Radiation source: fine-focus sealed tube	2895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ & ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −23→23
T_min = 0.933, T_max = 0.943	k = −13→13
13796 measured reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.203	w = 1/[σ²(F_o²) + (0.1113P)² + 2.2166P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3926 reflections	Δρ_max = 0.49 e Å⁻³
255 parameters	Δρ_min = −0.41 e Å⁻³
65 restraints	Absolute structure: Flack (1983), 1927 Fridel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.5 (2)

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.0124 (4)	0.0746 (5)	0.2218 (7)	0.0672 (15)
H1	−0.0060	0.0194	0.1495	0.081*
C2	−0.0338 (4)	0.0925 (6)	0.2738 (7)	0.0755 (18)
H2	−0.0856	0.0520	0.2332	0.091*
C3	−0.0043 (4)	0.1701 (6)	0.3865 (8)	0.0776 (17)
H3	−0.0345	0.1785	0.4242	0.093*
C4	0.0694 (4)	0.2339 (5)	0.4407 (7)	0.0746 (16)
H4	0.0884	0.2868	0.5149	0.090*
C5	0.1166 (3)	0.2228 (5)	0.3898 (6)	0.0621 (13)
H5	0.1663	0.2681	0.4274	0.075*
C6	0.0876 (3)	0.1414 (5)	0.2800 (5)	0.0537 (12)
C7	0.1625 (3)	0.0050 (5)	0.2239 (5)	0.0556 (12)
H7	0.1460	−0.0616	0.2530	0.067*
C8	0.2108 (3)	−0.0160 (5)	0.1788 (5)	0.0548 (12)
H8	0.2272	−0.0971	0.1778	0.066*
C9	0.2369 (3)	0.0807 (5)	0.1335 (5)	0.0535 (12)
C10	0.2116 (3)	0.2004 (5)	0.1416 (5)	0.0600 (13)
H10	0.2280	0.2682	0.1140	0.072*
C11	0.1632 (3)	0.2204 (5)	0.1894 (5)	0.0586 (13)
H11	0.1482	0.3010	0.1957	0.070*
C12	0.2873 (3)	0.0638 (5)	0.0829 (5)	0.0569 (12)
H12	0.3022	0.1343	0.0566	0.068*
C13	0.3147 (3)	−0.0474 (5)	0.0709 (5)	0.0560 (12)
H13	0.2995	−0.1165	0.0990	0.067*
C14	0.3642 (3)	−0.0719 (5)	0.0201 (5)	0.0541 (12)
C15	0.3748 (4)	−0.1927 (5)	−0.0088 (6)	0.0614 (13)
H15	0.3505	−0.2577	0.0080	0.074*
C16	0.4201 (4)	−0.2204 (5)	−0.0616 (6)	0.0656 (14)
H16	0.4237	−0.3024	−0.0826	0.079*
C17	0.4603 (3)	−0.1265 (5)	−0.0834 (6)	0.0600 (13)
C18	0.4494 (3)	−0.0039 (5)	−0.0559 (6)	0.0626 (13)
H18	0.4744	0.0610	−0.0715	0.075*
C19	0.4029 (3)	0.0225 (5)	−0.0064 (5)	0.0591 (13)
H19	0.3967	0.1050	0.0100	0.071*
C20	0.5037 (5)	−0.2756 (7)	−0.1855 (8)	0.091 (2)
H20A	0.5358	−0.3311	−0.1083	0.137*
H20B	0.5284	−0.2734	−0.2353	0.137*
H20C	0.4462	−0.3045	−0.2453	0.137*
C21	0.5524 (4)	−0.0558 (7)	−0.1456 (7)	0.0751 (16)
H21A	0.5151	0.0107	−0.2024	0.113*
H21B	0.5792	−0.0895	−0.1855	0.113*
H21C	0.5950	−0.0244	−0.0550	0.113*
N1	0.5049 (3)	−0.1511 (5)	−0.1362 (5)	0.0724 (13)
N2	0.1375 (2)	0.1224 (4)	0.2273 (4)	0.0515 (10)
P1	0.26522 (10)	−0.40739 (11)	0.33958 (15)	0.0597 (4)
F5	0.1834 (3)	−0.4680 (5)	0.2131 (5)	0.1541 (16)
F4	0.3249 (3)	−0.5071 (4)	0.3457 (7)	0.1356 (14)
F3	0.3451 (3)	−0.3462 (6)	0.4685 (5)	0.1541 (16)
F2	0.2065 (3)	−0.3017 (4)	0.3315 (7)	0.1356 (14)
F6	0.2762 (3)	−0.3260 (6)	0.2444 (6)	0.1486 (17)
F1	0.2515 (3)	−0.4916 (5)	0.4289 (6)	0.1486 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.054 (3)	0.051 (3)	0.085 (4)	0.003 (2)	0.034 (3)	0.011 (3)
C2	0.063 (4)	0.061 (4)	0.097 (5)	0.006 (3)	0.044 (4)	0.024 (3)
C3	0.076 (4)	0.067 (4)	0.104 (5)	0.022 (3)	0.060 (4)	0.023 (4)
C4	0.069 (4)	0.058 (3)	0.090 (4)	0.019 (3)	0.043 (3)	0.002 (3)
C5	0.054 (3)	0.049 (3)	0.068 (3)	0.010 (2)	0.028 (3)	0.003 (2)
C6	0.050 (3)	0.042 (2)	0.060 (3)	0.004 (2)	0.027 (2)	0.009 (2)
C7	0.065 (3)	0.043 (3)	0.051 (3)	−0.007 (2)	0.029 (2)	0.004 (2)
C8	0.063 (3)	0.043 (3)	0.058 (3)	−0.007 (2)	0.035 (2)	0.002 (2)
C9	0.052 (3)	0.051 (3)	0.042 (2)	−0.002 (2)	0.019 (2)	0.0032 (19)
C10	0.059 (3)	0.049 (3)	0.061 (3)	−0.008 (2)	0.029 (3)	0.012 (2)
C11	0.058 (3)	0.043 (3)	0.061 (3)	0.002 (2)	0.027 (3)	0.007 (2)
C12	0.057 (3)	0.059 (3)	0.048 (2)	−0.011 (2)	0.027 (2)	0.006 (2)
C13	0.053 (3)	0.053 (3)	0.050 (3)	−0.006 (2)	0.024 (2)	0.005 (2)
C14	0.046 (3)	0.050 (3)	0.049 (2)	−0.006 (2)	0.018 (2)	0.003 (2)
C15	0.058 (3)	0.044 (3)	0.065 (3)	−0.006 (2)	0.027 (3)	0.001 (2)
C16	0.063 (3)	0.039 (3)	0.074 (3)	0.003 (2)	0.029 (3)	0.001 (2)
C17	0.054 (3)	0.048 (3)	0.056 (3)	0.002 (2)	0.020 (2)	−0.005 (2)
C18	0.062 (3)	0.047 (3)	0.076 (3)	−0.014 (2)	0.039 (3)	−0.009 (2)
C19	0.069 (3)	0.042 (3)	0.070 (3)	−0.008 (2)	0.042 (3)	−0.009 (2)
C20	0.085 (4)	0.081 (4)	0.096 (5)	0.009 (4)	0.046 (4)	−0.030 (4)
C21	0.063 (3)	0.086 (4)	0.082 (4)	0.003 (3)	0.045 (3)	−0.007 (3)
N1	0.067 (3)	0.058 (3)	0.091 (3)	−0.003 (2)	0.046 (3)	−0.019 (2)
N2	0.050 (2)	0.040 (2)	0.052 (2)	−0.0041 (16)	0.0224 (19)	0.0060 (16)
P1	0.0620 (7)	0.0432 (6)	0.0712 (8)	0.0011 (6)	0.0376 (6)	0.0017 (6)
F5	0.116 (3)	0.133 (3)	0.129 (3)	−0.033 (2)	0.025 (2)	−0.040 (2)
F4	0.150 (3)	0.080 (2)	0.227 (4)	0.0386 (19)	0.139 (3)	0.023 (2)
F3	0.116 (3)	0.133 (3)	0.129 (3)	−0.033 (2)	0.025 (2)	−0.040 (2)
F2	0.150 (3)	0.080 (2)	0.227 (4)	0.0386 (19)	0.139 (3)	0.023 (2)
F6	0.159 (3)	0.155 (3)	0.194 (4)	0.054 (3)	0.138 (3)	0.096 (3)
F1	0.159 (3)	0.155 (3)	0.194 (4)	0.054 (3)	0.138 (3)	0.096 (3)

Geometric parameters (Å, º) top

C1—C2	1.375 (9)	C13—H13	0.9300
C1—C6	1.395 (8)	C14—C15	1.389 (7)
C1—H1	0.9300	C14—C19	1.406 (7)
C2—C3	1.391 (10)	C15—C16	1.384 (8)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.363 (9)	C16—C17	1.392 (8)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.372 (9)	C17—N1	1.366 (7)
C4—H4	0.9300	C17—C18	1.403 (7)
C5—C6	1.393 (7)	C18—C19	1.371 (7)
C5—H5	0.9300	C18—H18	0.9300
C6—N2	1.449 (7)	C19—H19	0.9300
C7—C8	1.350 (7)	C20—N1	1.456 (8)
C7—N2	1.360 (6)	C20—H20A	0.9600
C7—H7	0.9300	C20—H20B	0.9600
C8—C9	1.397 (7)	C20—H20C	0.9600
C8—H8	0.9300	C21—N1	1.428 (8)
C9—C10	1.401 (7)	C21—H21A	0.9600
C9—C12	1.435 (8)	C21—H21B	0.9600
C10—C11	1.375 (8)	C21—H21C	0.9600
C10—H10	0.9300	P1—F1	1.539 (4)
C11—N2	1.353 (6)	P1—F6	1.547 (4)
C11—H11	0.9300	P1—F4	1.550 (4)
C12—C13	1.348 (8)	P1—F3	1.555 (4)
C12—H12	0.9300	P1—F5	1.557 (4)
C13—C14	1.433 (7)	P1—F2	1.574 (4)

C2—C1—C6	118.4 (6)	C15—C16—C17	120.5 (5)
C2—C1—H1	120.8	C15—C16—H16	119.8
C6—C1—H1	120.8	C17—C16—H16	119.8
C1—C2—C3	121.0 (6)	N1—C17—C16	121.7 (5)
C1—C2—H2	119.5	N1—C17—C18	121.0 (5)
C3—C2—H2	119.5	C16—C17—C18	117.2 (5)
C4—C3—C2	118.9 (6)	C19—C18—C17	121.6 (5)
C4—C3—H3	120.5	C19—C18—H18	119.2
C2—C3—H3	120.5	C17—C18—H18	119.2
C3—C4—C5	122.5 (6)	C18—C19—C14	121.6 (5)
C3—C4—H4	118.8	C18—C19—H19	119.2
C5—C4—H4	118.8	C14—C19—H19	119.2
C4—C5—C6	117.8 (6)	N1—C20—H20A	109.5
C4—C5—H5	121.1	N1—C20—H20B	109.5
C6—C5—H5	121.1	H20A—C20—H20B	109.5
C5—C6—C1	121.4 (5)	N1—C20—H20C	109.5
C5—C6—N2	119.6 (4)	H20A—C20—H20C	109.5
C1—C6—N2	119.0 (5)	H20B—C20—H20C	109.5
C8—C7—N2	120.8 (5)	N1—C21—H21A	109.5
C8—C7—H7	119.6	N1—C21—H21B	109.5
N2—C7—H7	119.6	H21A—C21—H21B	109.5
C7—C8—C9	121.9 (5)	N1—C21—H21C	109.5
C7—C8—H8	119.1	H21A—C21—H21C	109.5
C9—C8—H8	119.1	H21B—C21—H21C	109.5
C8—C9—C10	115.6 (5)	C17—N1—C21	120.9 (5)
C8—C9—C12	124.3 (5)	C17—N1—C20	120.1 (6)
C10—C9—C12	120.1 (5)	C21—N1—C20	119.0 (5)
C11—C10—C9	121.8 (5)	C11—N2—C7	120.2 (5)
C11—C10—H10	119.1	C11—N2—C6	120.6 (4)
C9—C10—H10	119.1	C7—N2—C6	119.1 (4)
N2—C11—C10	119.7 (5)	F1—P1—F6	177.6 (4)
N2—C11—H11	120.2	F1—P1—F4	89.5 (3)
C10—C11—H11	120.2	F6—P1—F4	90.1 (3)
C13—C12—C9	124.5 (5)	F1—P1—F3	92.2 (3)
C13—C12—H12	117.7	F6—P1—F3	90.1 (3)
C9—C12—H12	117.7	F4—P1—F3	87.7 (3)
C12—C13—C14	127.8 (5)	F1—P1—F5	86.3 (3)
C12—C13—H13	116.1	F6—P1—F5	91.4 (3)
C14—C13—H13	116.1	F4—P1—F5	93.9 (3)
C15—C14—C19	116.1 (5)	F3—P1—F5	177.8 (4)
C15—C14—C13	120.8 (5)	F1—P1—F2	92.9 (3)
C19—C14—C13	123.1 (5)	F6—P1—F2	87.5 (3)
C16—C15—C14	122.9 (5)	F4—P1—F2	177.5 (3)
C16—C15—H15	118.6	F3—P1—F2	91.4 (3)
C14—C15—H15	118.6	F5—P1—F2	87.1 (3)

C6—C1—C2—C3	−3.3 (8)	C14—C15—C16—C17	2.4 (8)
C1—C2—C3—C4	3.4 (9)	C15—C16—C17—N1	−179.6 (5)
C2—C3—C4—C5	−1.1 (9)	C15—C16—C17—C18	−2.9 (8)
C3—C4—C5—C6	−1.0 (8)	N1—C17—C18—C19	178.2 (5)
C4—C5—C6—C1	1.0 (7)	C16—C17—C18—C19	1.5 (8)
C4—C5—C6—N2	−177.1 (5)	C17—C18—C19—C14	0.5 (8)
C2—C1—C6—C5	1.1 (8)	C15—C14—C19—C18	−1.0 (7)
C2—C1—C6—N2	179.2 (5)	C13—C14—C19—C18	−179.6 (5)
N2—C7—C8—C9	−0.2 (7)	C16—C17—N1—C21	−173.9 (5)
C7—C8—C9—C10	1.7 (7)	C18—C17—N1—C21	9.5 (8)
C7—C8—C9—C12	−179.2 (5)	C16—C17—N1—C20	6.8 (9)
C8—C9—C10—C11	−0.9 (7)	C18—C17—N1—C20	−169.8 (6)
C12—C9—C10—C11	179.9 (5)	C10—C11—N2—C7	2.9 (7)
C9—C10—C11—N2	−1.4 (8)	C10—C11—N2—C6	179.0 (4)
C8—C9—C12—C13	1.0 (8)	C8—C7—N2—C11	−2.1 (7)
C10—C9—C12—C13	−179.9 (5)	C8—C7—N2—C6	−178.3 (4)
C9—C12—C13—C14	179.2 (5)	C5—C6—N2—C11	−53.1 (6)
C12—C13—C14—C15	−168.5 (5)	C1—C6—N2—C11	128.8 (5)
C12—C13—C14—C19	10.0 (8)	C5—C6—N2—C7	123.1 (5)
C19—C14—C15—C16	−0.4 (8)	C1—C6—N2—C7	−55.0 (6)
C13—C14—C15—C16	178.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···F6	0.93	2.59	3.486 (8)	162
C11—H11···F5ⁱ	0.93	2.55	3.363 (8)	146
C16—H16···F4ⁱⁱ	0.93	2.59	3.289 (7)	132
C21—H21B···F2ⁱⁱⁱ	0.96	2.64	3.516 (8)	152

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

Acknowledgements

The authors thank Dr P. K. Sudadevi Antharjanam, SAIF, IIT, Chennai, India, for the X-ray intensity data collection.

References

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Volume 75| Part 2| February 2019| Pages 288-291

https://doi.org/10.1107/S2056989019001403

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