1-Benzyl-3-(8-methoxy­quinolin-2-yl­methyl)­imidazolium hexa­fluorido­phosphate

Fan, X.-N.; XiaHou, G.-L.; Huang, Z.-Q.; Ding, Y.-C.

doi:10.1107/S1600536807038767

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1-Benzyl-3-(8-methoxyquinolin-2-ylmethyl)imidazolium hexafluoridophosphate

X.-N. Fan, G.-L. XiaHou, Z.-Q. Huang and Y.-C. Ding

The asymmetric unit of the title compound, C₂₁H₂₀N₃O⁺·PF₆⁻, contains two independent 1-benzyl-3-(8-methoxyquinolin-2-ylmethyl)imidazolium cationic units and two PF₆⁻ ions. The two cationic units differ slightly in the orientations of the benzylimidazolium group with respect to the quinoline ring system. In one of the cationic units, the quinoline ring system and the phenyl ring form dihedral angles of 76.0 (1) and 73.8 (1)°, respectively, with the central five-membered ring, and in the other unit these angles are 85.6 (1) and 69.0 (2)°, respectively. Both hexafluoridophosphate ions are found to be disordered over two positions, with site occupancies of ca 0.74 and 0.26. The crystal packing is stabilized by C—H

F and C—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038767/ci2422sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038767/ci2422Isup2.hkl Contains datablock I

CCDC reference: 660272

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.008 Å
Disorder in solvent or counterion
R factor = 0.065
wR factor = 0.215
Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.06
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        300 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        300 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.81 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C36
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C41
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C37
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        P1'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        P2'
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C37    -C42           1.36 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        240

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  19 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Numerous flexible and rigid N-heterocyclic carbene precursors have been synthesized and studied. They have attracted considerable attention because of their diverse coordination capabilities and the important catalytic properties of their metal complexes (Herrmann, 2002; Herrmann & Kocher, 1997). We report here the crystal structure of the title compound.

The asymmetric unit of the title compound contains two independent [C₂₁H₂₀N₃O]⁺ cationic units and two PF₆^- ions (Fig. 1). The two cationic units differ in the orientations of the benzylimidazolium group with respect to the quinoline ring system. Bond lengths and angles in the title compound show normal values. The quinoline ring system in each independent molecule is planar.

The N1/C1–C9 and C16–C21 planes form dihedral angles of 76.0 (1)° and 73.8 (1)°, respectively, with the N2/N3/C12–C14 plane. The N6/C22–C30 and C37–C42 planes form dihedral angles of 85.6 (1)° and 69.0 (2)°, respectively, with the N2/N3/C12–C14 plane.

As can be seen from Fig. 2, the hexafluorophosphate ions are linked to 1-benzyl-3-(2-methylene-8-methoxy-quinoline)imidazolium ions through C—H···F hydrogen bonds (Table 1). A C—H···N hydrogen bond is also observed.

Related literature top

For general background, see: Herrmann (2002); Herrmann & Kocher (1997). For synthesis, see: Lee et al. (2004).

Experimental top

The title compound was synthesized by the reaction of 2-bromomethyl-8-methoxy-quinoline (0.25 g) with 1-benzyl-1H-imidazole (0.2 g) in tetrahydrofuran at 350 K, according to a literature method (Lee et al., 2004). A white precipitate was obtained, and it was dissolved in methol (5 ml) and then ammonium hexafluorophosphate (0.2 g) was added. The resulting solid was filtered off, washed with ethyl ether and air-dried. White single crystals suitable for X-ray diffraction were obtained by recrystallization from absolute acetionitrile and ethyl ether (1:2).

Structure description top

For general background, see: Herrmann (2002); Herrmann & Kocher (1997). For synthesis, see: Lee et al. (2004).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. Only the major disorder component is shown.
	Fig. 2. The crystal of the packing of the title compound, viewed along the a axis. C—H···F and C—H···N hydrogen bonds are shown as dashed lines. Only the major disorder component is shown.

1-Benzyl-3-(8-methoxyquinolin-2-ylmethyl)imidazolium hexafluoridophosphate top

Crystal data top

C₂₁H₂₀N₃O⁺·F₆P⁻	Z = 4
M_r = 475.37	F(000) = 976
Triclinic, P1	D_x = 1.433 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.272 (3) Å	Cell parameters from 2858 reflections
b = 12.537 (3) Å	θ = 2.7–23.6°
c = 14.361 (3) Å	µ = 0.19 mm⁻¹
α = 90.847 (3)°	T = 291 K
β = 91.539 (3)°	Block, white
γ = 93.809 (3)°	0.49 × 0.45 × 0.43 mm
V = 2203.5 (8) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	7961 independent reflections
Radiation source: fine-focus sealed tube	4602 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −14→14
T_min = 0.911, T_max = 0.922	k = −15→15
15491 measured reflections	l = −17→17

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)] = 0.065	H-atom parameters constrained
wR(F²) = 0.215	w = 1/[σ²(F_o²) + (0.0928P)² + 1.4093P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
7961 reflections	Δρ_max = 0.50 e Å⁻³
708 parameters	Δρ_min = −0.24 e Å⁻³
240 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (11)

Crystal data top

C₂₁H₂₀N₃O⁺·F₆P⁻	γ = 93.809 (3)°
M_r = 475.37	V = 2203.5 (8) Å³
Triclinic, P1	Z = 4
a = 12.272 (3) Å	Mo Kα radiation
b = 12.537 (3) Å	µ = 0.19 mm⁻¹
c = 14.361 (3) Å	T = 291 K
α = 90.847 (3)°	0.49 × 0.45 × 0.43 mm
β = 91.539 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	7961 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	4602 reflections with I > 2σ(I)
T_min = 0.911, T_max = 0.922	R_int = 0.038
15491 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	240 restraints
wR(F²) = 0.215	H-atom parameters constrained
S = 1.05	Δρ_max = 0.50 e Å⁻³
7961 reflections	Δρ_min = −0.24 e Å⁻³
708 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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)
P1	0.6866 (3)	0.2339 (3)	0.4728 (3)	0.0605 (19)	0.742 (10)
F1	0.6701 (4)	0.2242 (6)	0.3625 (3)	0.109 (2)	0.742 (10)
F2	0.7707 (5)	0.1462 (5)	0.4689 (5)	0.124 (2)	0.742 (10)
F3	0.5890 (6)	0.1459 (6)	0.4837 (5)	0.111 (2)	0.742 (10)
F4	0.7030 (4)	0.2430 (5)	0.5810 (3)	0.104 (2)	0.742 (10)
F5	0.6003 (5)	0.3196 (5)	0.4755 (5)	0.135 (3)	0.742 (10)
F6	0.7822 (5)	0.3205 (5)	0.4588 (4)	0.109 (2)	0.742 (10)
P1'	0.6893 (9)	0.2309 (9)	0.4643 (8)	0.063 (6)	0.258 (10)
F1'	0.7114 (11)	0.1534 (11)	0.3811 (10)	0.090 (5)	0.258 (10)
F2'	0.7923 (13)	0.1921 (16)	0.5154 (13)	0.158 (9)	0.258 (10)
F3'	0.6187 (16)	0.1361 (14)	0.5069 (14)	0.124 (9)	0.258 (10)
F4'	0.6676 (14)	0.3058 (15)	0.5485 (13)	0.140 (7)	0.258 (10)
F5'	0.5902 (10)	0.2719 (14)	0.4092 (13)	0.128 (7)	0.258 (10)
F6'	0.7659 (12)	0.3220 (10)	0.4227 (13)	0.094 (6)	0.258 (10)
P2	0.1795 (4)	0.7468 (4)	0.0546 (3)	0.0571 (12)	0.739 (19)
F7	0.2725 (6)	0.6773 (5)	0.0189 (7)	0.110 (3)	0.739 (19)
F8	0.1989 (5)	0.7013 (7)	0.1553 (4)	0.090 (2)	0.739 (19)
F9	0.0912 (8)	0.6513 (7)	0.0333 (7)	0.114 (3)	0.739 (19)
F10	0.0869 (6)	0.8149 (7)	0.0922 (7)	0.130 (3)	0.739 (19)
F11	0.1606 (9)	0.7891 (6)	−0.0466 (4)	0.116 (3)	0.739 (19)
F12	0.2675 (6)	0.8413 (6)	0.0764 (6)	0.092 (2)	0.739 (19)
P2'	0.1689 (11)	0.7337 (12)	0.0456 (10)	0.067 (5)	0.261 (19)
F7'	0.2338 (19)	0.6744 (15)	−0.0290 (19)	0.129 (8)	0.261 (19)
F8'	0.2211 (17)	0.6680 (15)	0.1248 (17)	0.101 (7)	0.261 (19)
F9'	0.0738 (13)	0.6427 (13)	0.0332 (13)	0.062 (5)	0.261 (19)
F10'	0.1024 (19)	0.7933 (17)	0.1193 (12)	0.113 (7)	0.261 (19)
F11'	0.1105 (19)	0.7986 (15)	−0.0311 (12)	0.104 (7)	0.261 (19)
F12'	0.2669 (16)	0.8208 (16)	0.0533 (18)	0.109 (9)	0.261 (19)
O1	0.7717 (3)	0.6213 (3)	0.5771 (3)	0.0933 (11)
O2	0.7504 (2)	−0.1017 (2)	1.0211 (2)	0.0746 (9)
N1	0.9222 (3)	0.6509 (3)	0.4472 (2)	0.0546 (8)
N2	1.0364 (3)	0.4949 (3)	0.3131 (2)	0.0541 (8)
N3	0.9645 (3)	0.3409 (3)	0.2674 (2)	0.0564 (9)
N4	0.5105 (3)	0.1467 (3)	0.7904 (3)	0.0608 (9)
N5	0.4442 (2)	−0.0133 (3)	0.8162 (2)	0.0520 (8)
N6	0.5660 (3)	−0.1618 (2)	0.9259 (2)	0.0508 (8)
C1	0.7622 (4)	0.7075 (4)	0.5216 (4)	0.0701 (12)
C2	0.6811 (4)	0.7791 (5)	0.5282 (4)	0.0916 (17)
H2	0.6277	0.7697	0.5726	0.110*
C3	0.6800 (5)	0.8665 (5)	0.4669 (5)	0.103 (2)
H3	0.6248	0.9136	0.4713	0.124*
C4	0.7548 (5)	0.8831 (4)	0.4037 (5)	0.0972 (18)
H4	0.7527	0.9422	0.3655	0.117*
C5	0.8392 (4)	0.8110 (4)	0.3936 (3)	0.0713 (13)
C6	0.9207 (5)	0.8250 (4)	0.3281 (3)	0.0872 (16)
H6	0.9211	0.8825	0.2879	0.105*
C7	1.0005 (5)	0.7529 (4)	0.3233 (3)	0.0805 (14)
H7	1.0561	0.7618	0.2808	0.097*
C8	0.9964 (3)	0.6664 (3)	0.3835 (3)	0.0577 (10)
C9	0.8432 (3)	0.7221 (3)	0.4532 (3)	0.0580 (10)
C10	0.6958 (6)	0.6066 (7)	0.6503 (6)	0.170 (4)
H10A	0.7016	0.6682	0.6910	0.255*
H10B	0.7120	0.5444	0.6850	0.255*
H10C	0.6230	0.5972	0.6241	0.255*
C11	1.0793 (4)	0.5831 (3)	0.3756 (3)	0.0650 (12)
H11A	1.1465	0.6154	0.3513	0.078*
H11B	1.0956	0.5554	0.4368	0.078*
C12	1.0219 (4)	0.4975 (4)	0.2186 (3)	0.0746 (14)
H12	1.0397	0.5553	0.1808	0.090*
C13	0.9773 (4)	0.4018 (4)	0.1901 (3)	0.0714 (13)
H13	0.9586	0.3808	0.1291	0.086*
C14	1.0005 (3)	0.3990 (3)	0.3407 (3)	0.0561 (10)
H14	1.0007	0.3761	0.4020	0.067*
C15	0.9222 (4)	0.2273 (4)	0.2682 (3)	0.0706 (12)
H15A	0.8832	0.2097	0.2098	0.085*
H15B	0.8708	0.2177	0.3181	0.085*
C16	1.0119 (4)	0.1517 (3)	0.2818 (3)	0.0630 (11)
C17	1.0769 (5)	0.1275 (4)	0.2090 (4)	0.0953 (18)
H17	1.0663	0.1589	0.1515	0.114*
C18	1.1584 (6)	0.0565 (5)	0.2203 (6)	0.118 (2)
H18	1.2016	0.0392	0.1708	0.142*
C19	1.1735 (5)	0.0125 (5)	0.3066 (7)	0.114 (2)
H19	1.2296	−0.0328	0.3166	0.137*
C20	1.1069 (6)	0.0351 (5)	0.3772 (5)	0.1038 (19)
H20	1.1157	0.0023	0.4343	0.125*
C21	1.0275 (5)	0.1047 (4)	0.3660 (3)	0.0823 (15)
H21	0.9838	0.1205	0.4156	0.099*
C22	0.7408 (3)	−0.2053 (3)	0.9897 (3)	0.0575 (11)
C23	0.8181 (4)	−0.2779 (4)	1.0050 (3)	0.0728 (13)
H23	0.8827	−0.2575	1.0378	0.087*
C24	0.7988 (5)	−0.3843 (4)	0.9703 (4)	0.0889 (18)
H24	0.8512	−0.4333	0.9809	0.107*
C25	0.7063 (5)	−0.4156 (4)	0.9225 (4)	0.0896 (17)
H25	0.6950	−0.4860	0.9010	0.108*
C26	0.6255 (4)	−0.3418 (3)	0.9046 (3)	0.0672 (12)
C27	0.5275 (5)	−0.3680 (4)	0.8540 (4)	0.0865 (16)
H27	0.5131	−0.4372	0.8304	0.104*
C28	0.4540 (4)	−0.2938 (4)	0.8392 (4)	0.0763 (13)
H28	0.3903	−0.3106	0.8040	0.092*
C29	0.4759 (4)	−0.1903 (3)	0.8782 (3)	0.0554 (10)
C30	0.6423 (3)	−0.2354 (3)	0.9388 (3)	0.0525 (10)
C31	0.8499 (5)	−0.0659 (5)	1.0692 (5)	0.109 (2)
H31A	0.8569	−0.1047	1.1259	0.164*
H31B	0.8490	0.0091	1.0834	0.164*
H31C	0.9106	−0.0780	1.0305	0.164*
C32	0.3959 (3)	−0.1062 (3)	0.8645 (3)	0.0663 (12)
H32A	0.3329	−0.1364	0.8286	0.080*
H32B	0.3710	−0.0834	0.9247	0.080*
C33	0.4784 (4)	−0.0108 (4)	0.7262 (3)	0.0686 (13)
H33	0.4739	−0.0678	0.6838	0.082*
C34	0.5190 (4)	0.0879 (4)	0.7103 (3)	0.0719 (13)
H34	0.5480	0.1125	0.6548	0.086*
C35	0.4652 (3)	0.0829 (3)	0.8536 (3)	0.0566 (10)
H35	0.4507	0.1028	0.9144	0.068*
C36	0.5422 (4)	0.2627 (4)	0.8036 (4)	0.0841 (15)
H36A	0.6111	0.2791	0.7736	0.101*
H36B	0.5534	0.2784	0.8696	0.101*
C37	0.4588 (4)	0.3331 (3)	0.7649 (3)	0.0614 (11)
C38	0.4690 (5)	0.3775 (4)	0.6792 (4)	0.0932 (18)
H38	0.5280	0.3625	0.6431	0.112*
C39	0.3919 (7)	0.4451 (5)	0.6449 (4)	0.110 (2)
H39	0.3993	0.4748	0.5863	0.132*
C40	0.3081 (6)	0.4664 (5)	0.6967 (6)	0.103 (2)
H40	0.2564	0.5108	0.6734	0.123*
C41	0.2958 (5)	0.4252 (5)	0.7827 (6)	0.119 (2)
H41	0.2375	0.4421	0.8190	0.143*
C42	0.3715 (4)	0.3580 (5)	0.8149 (4)	0.0934 (17)
H42	0.3626	0.3282	0.8734	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.057 (3)	0.065 (3)	0.059 (2)	−0.001 (2)	0.0093 (17)	−0.0002 (16)
F1	0.114 (4)	0.147 (5)	0.062 (2)	−0.018 (4)	−0.008 (2)	0.005 (3)
F2	0.131 (4)	0.106 (4)	0.144 (5)	0.056 (3)	0.035 (4)	0.025 (4)
F3	0.094 (4)	0.131 (5)	0.103 (4)	−0.043 (3)	0.015 (3)	0.005 (3)
F4	0.114 (4)	0.135 (4)	0.060 (2)	−0.021 (3)	0.006 (2)	0.011 (2)
F5	0.140 (4)	0.127 (4)	0.150 (5)	0.069 (4)	0.036 (4)	0.015 (4)
F6	0.122 (4)	0.127 (4)	0.067 (3)	−0.067 (3)	0.002 (3)	−0.002 (3)
P1'	0.072 (9)	0.063 (8)	0.054 (6)	0.013 (6)	0.002 (5)	0.009 (5)
F1'	0.086 (8)	0.084 (8)	0.097 (8)	−0.027 (6)	0.017 (6)	−0.030 (6)
F2'	0.146 (11)	0.170 (12)	0.159 (12)	0.046 (9)	−0.063 (9)	−0.017 (9)
F3'	0.151 (13)	0.113 (11)	0.106 (11)	−0.030 (8)	0.021 (8)	0.032 (8)
F4'	0.143 (10)	0.151 (11)	0.127 (10)	0.026 (8)	0.014 (8)	−0.064 (8)
F5'	0.099 (9)	0.141 (10)	0.148 (11)	0.039 (7)	−0.023 (8)	0.008 (8)
F6'	0.104 (9)	0.075 (8)	0.108 (10)	0.019 (7)	0.033 (7)	0.012 (7)
P2	0.055 (2)	0.063 (2)	0.0525 (15)	−0.0003 (15)	−0.0028 (13)	0.0094 (13)
F7	0.102 (4)	0.113 (4)	0.117 (5)	0.028 (3)	0.024 (4)	−0.017 (3)
F8	0.073 (3)	0.133 (5)	0.062 (3)	−0.014 (3)	−0.004 (2)	0.025 (3)
F9	0.116 (5)	0.110 (5)	0.106 (5)	−0.053 (4)	−0.029 (4)	0.017 (4)
F10	0.091 (4)	0.149 (5)	0.156 (6)	0.054 (4)	−0.023 (4)	−0.023 (4)
F11	0.137 (6)	0.118 (5)	0.086 (3)	−0.031 (4)	−0.036 (3)	0.047 (3)
F12	0.101 (4)	0.068 (3)	0.101 (4)	−0.019 (3)	−0.029 (3)	0.005 (3)
P2'	0.077 (8)	0.054 (6)	0.069 (6)	0.008 (5)	−0.020 (4)	0.000 (4)
F7'	0.117 (10)	0.140 (10)	0.132 (11)	0.026 (8)	0.026 (8)	−0.028 (8)
F8'	0.092 (9)	0.085 (9)	0.123 (11)	−0.002 (7)	−0.031 (8)	0.022 (8)
F9'	0.063 (8)	0.063 (8)	0.060 (8)	−0.002 (6)	−0.013 (6)	0.014 (6)
F10'	0.135 (12)	0.133 (11)	0.076 (8)	0.033 (8)	0.026 (7)	−0.017 (7)
F11'	0.105 (10)	0.102 (9)	0.105 (9)	0.013 (8)	−0.028 (7)	0.023 (7)
F12'	0.109 (12)	0.115 (12)	0.097 (11)	−0.039 (8)	−0.002 (7)	0.027 (8)
O1	0.072 (2)	0.101 (3)	0.110 (3)	0.013 (2)	0.030 (2)	0.022 (2)
O2	0.0577 (19)	0.063 (2)	0.102 (2)	0.0048 (16)	−0.0140 (17)	−0.0068 (17)
N1	0.055 (2)	0.051 (2)	0.0564 (18)	0.0001 (16)	−0.0056 (16)	−0.0050 (15)
N2	0.056 (2)	0.059 (2)	0.0463 (17)	0.0007 (17)	0.0026 (15)	−0.0092 (15)
N3	0.059 (2)	0.057 (2)	0.0531 (19)	0.0007 (17)	0.0041 (16)	−0.0035 (16)
N4	0.050 (2)	0.049 (2)	0.082 (2)	0.0018 (17)	−0.0129 (18)	0.0037 (18)
N5	0.0478 (19)	0.050 (2)	0.0583 (19)	0.0068 (16)	−0.0031 (15)	0.0049 (15)
N6	0.055 (2)	0.0427 (18)	0.0558 (18)	0.0048 (16)	0.0052 (16)	0.0068 (14)
C1	0.056 (3)	0.066 (3)	0.088 (3)	0.006 (2)	−0.009 (2)	−0.002 (3)
C2	0.058 (3)	0.096 (4)	0.121 (5)	0.016 (3)	−0.004 (3)	−0.021 (4)
C3	0.089 (4)	0.084 (4)	0.139 (6)	0.037 (4)	−0.021 (4)	−0.020 (4)
C4	0.108 (5)	0.066 (4)	0.119 (5)	0.029 (3)	−0.027 (4)	0.004 (3)
C5	0.089 (4)	0.050 (3)	0.073 (3)	0.007 (2)	−0.019 (3)	−0.006 (2)
C6	0.127 (5)	0.067 (3)	0.067 (3)	0.000 (3)	−0.012 (3)	0.010 (2)
C7	0.105 (4)	0.072 (3)	0.064 (3)	−0.004 (3)	0.009 (3)	0.000 (2)
C8	0.067 (3)	0.054 (3)	0.051 (2)	−0.002 (2)	−0.008 (2)	−0.0080 (19)
C9	0.060 (3)	0.048 (2)	0.064 (2)	0.001 (2)	−0.013 (2)	−0.0110 (19)
C10	0.126 (6)	0.206 (9)	0.191 (8)	0.042 (6)	0.094 (6)	0.081 (7)
C11	0.060 (3)	0.070 (3)	0.063 (3)	0.000 (2)	−0.003 (2)	−0.016 (2)
C12	0.104 (4)	0.066 (3)	0.053 (2)	−0.004 (3)	0.013 (2)	0.006 (2)
C13	0.104 (4)	0.065 (3)	0.044 (2)	−0.003 (3)	0.001 (2)	−0.001 (2)
C14	0.061 (3)	0.061 (3)	0.047 (2)	0.004 (2)	0.0070 (19)	0.0032 (19)
C15	0.066 (3)	0.064 (3)	0.080 (3)	−0.009 (2)	0.003 (2)	0.000 (2)
C16	0.074 (3)	0.052 (3)	0.062 (2)	−0.008 (2)	0.005 (2)	0.000 (2)
C17	0.124 (5)	0.089 (4)	0.077 (3)	0.028 (4)	0.033 (3)	0.013 (3)
C18	0.125 (5)	0.093 (5)	0.141 (6)	0.021 (4)	0.048 (5)	0.007 (4)
C19	0.086 (4)	0.073 (4)	0.184 (8)	0.009 (3)	−0.006 (5)	0.021 (5)
C20	0.119 (5)	0.083 (4)	0.107 (5)	−0.005 (4)	−0.028 (4)	0.024 (3)
C21	0.113 (4)	0.065 (3)	0.068 (3)	−0.005 (3)	−0.002 (3)	0.005 (2)
C22	0.056 (3)	0.055 (3)	0.063 (2)	0.009 (2)	0.007 (2)	0.012 (2)
C23	0.058 (3)	0.081 (3)	0.083 (3)	0.018 (3)	0.006 (2)	0.022 (3)
C24	0.093 (4)	0.076 (4)	0.105 (4)	0.046 (3)	0.019 (3)	0.022 (3)
C25	0.109 (5)	0.057 (3)	0.107 (4)	0.032 (3)	0.009 (4)	−0.002 (3)
C26	0.085 (3)	0.050 (3)	0.069 (3)	0.018 (2)	0.006 (2)	−0.001 (2)
C27	0.117 (5)	0.054 (3)	0.088 (3)	0.006 (3)	−0.004 (3)	−0.019 (3)
C28	0.080 (3)	0.063 (3)	0.085 (3)	0.002 (3)	−0.012 (3)	−0.004 (3)
C29	0.055 (3)	0.054 (3)	0.057 (2)	−0.001 (2)	0.001 (2)	0.0095 (19)
C30	0.060 (3)	0.048 (2)	0.051 (2)	0.009 (2)	0.0112 (19)	0.0060 (17)
C31	0.086 (4)	0.099 (5)	0.139 (5)	0.004 (4)	−0.045 (4)	−0.015 (4)
C32	0.051 (3)	0.068 (3)	0.081 (3)	0.004 (2)	0.000 (2)	0.024 (2)
C33	0.097 (4)	0.061 (3)	0.050 (2)	0.015 (3)	0.003 (2)	−0.002 (2)
C34	0.083 (3)	0.066 (3)	0.069 (3)	0.013 (3)	0.014 (2)	0.015 (2)
C35	0.058 (3)	0.054 (3)	0.059 (2)	0.013 (2)	−0.0071 (19)	−0.002 (2)
C36	0.072 (3)	0.054 (3)	0.123 (4)	−0.004 (3)	−0.028 (3)	−0.001 (3)
C37	0.058 (3)	0.043 (2)	0.082 (3)	−0.005 (2)	−0.008 (2)	0.002 (2)
C38	0.135 (5)	0.069 (3)	0.077 (3)	0.012 (3)	0.026 (3)	−0.005 (3)
C39	0.188 (7)	0.067 (4)	0.075 (4)	0.014 (4)	−0.013 (4)	0.012 (3)
C40	0.104 (5)	0.064 (4)	0.137 (6)	0.003 (3)	−0.053 (4)	0.009 (4)
C41	0.090 (4)	0.114 (5)	0.160 (6)	0.033 (4)	0.023 (4)	0.058 (5)
C42	0.084 (4)	0.099 (4)	0.100 (4)	0.013 (3)	0.016 (3)	0.042 (3)

Geometric parameters (Å, º) top

P1—F2	1.559 (5)	C10—H10B	0.96
P1—F5	1.559 (5)	C10—H10C	0.96
P1—F4	1.563 (5)	C11—H11A	0.97
P1—F6	1.564 (5)	C11—H11B	0.97
P1—F3	1.586 (5)	C12—C13	1.339 (6)
P1—F1	1.592 (5)	C12—H12	0.93
P1'—F2'	1.554 (9)	C13—H13	0.93
P1'—F5'	1.554 (9)	C14—H14	0.93
P1'—F4'	1.559 (9)	C15—C16	1.510 (6)
P1'—F6'	1.566 (9)	C15—H15A	0.97
P1'—F3'	1.566 (10)	C15—H15B	0.97
P1'—F1'	1.569 (9)	C16—C21	1.367 (6)
P2—F10	1.569 (5)	C16—C17	1.375 (6)
P2—F12	1.571 (6)	C17—C18	1.389 (8)
P2—F11	1.572 (5)	C17—H17	0.93
P2—F7	1.573 (5)	C18—C19	1.378 (10)
P2—F8	1.580 (5)	C18—H18	0.93
P2—F9	1.581 (6)	C19—C20	1.358 (9)
P2'—F7'	1.561 (9)	C19—H19	0.93
P2'—F8'	1.563 (9)	C20—C21	1.359 (8)
P2'—F10'	1.565 (9)	C20—H20	0.93
P2'—F11'	1.565 (9)	C21—H21	0.93
P2'—F12'	1.570 (10)	C22—C23	1.373 (6)
P2'—F9'	1.581 (10)	C22—C30	1.421 (6)
O1—C1	1.361 (6)	C23—C24	1.420 (7)
O1—C10	1.429 (6)	C23—H23	0.93
O2—C22	1.365 (5)	C24—C25	1.344 (8)
O2—C31	1.428 (6)	C24—H24	0.93
N1—C8	1.316 (5)	C25—C26	1.422 (6)
N1—C9	1.364 (5)	C25—H25	0.93
N2—C14	1.323 (5)	C26—C27	1.405 (7)
N2—C12	1.365 (5)	C26—C30	1.415 (6)
N2—C11	1.474 (5)	C27—C28	1.354 (7)
N3—C14	1.321 (5)	C27—H27	0.93
N3—C13	1.362 (5)	C28—C29	1.411 (6)
N3—C15	1.483 (5)	C28—H28	0.93
N4—C35	1.326 (5)	C29—C32	1.500 (5)
N4—C34	1.368 (6)	C31—H31A	0.96
N4—C36	1.489 (6)	C31—H31B	0.96
N5—C35	1.319 (5)	C31—H31C	0.96
N5—C33	1.370 (5)	C32—H32A	0.97
N5—C32	1.464 (5)	C32—H32B	0.97
N6—C29	1.312 (5)	C33—C34	1.328 (6)
N6—C30	1.370 (5)	C33—H33	0.93
C1—C2	1.388 (6)	C34—H34	0.93
C1—C9	1.421 (6)	C35—H35	0.93
C2—C3	1.417 (8)	C36—C37	1.496 (6)
C2—H2	0.93	C36—H36A	0.97
C3—C4	1.316 (8)	C36—H36B	0.97
C3—H3	0.93	C37—C42	1.357 (6)
C4—C5	1.427 (7)	C37—C38	1.363 (7)
C4—H4	0.93	C38—C39	1.396 (8)
C5—C6	1.396 (7)	C38—H38	0.93
C5—C9	1.419 (6)	C39—C40	1.324 (9)
C6—C7	1.379 (7)	C39—H39	0.93
C6—H6	0.93	C40—C41	1.355 (9)
C7—C8	1.396 (6)	C40—H40	0.93
C7—H7	0.93	C41—C42	1.371 (7)
C8—C11	1.510 (5)	C41—H41	0.93
C10—H10A	0.96	C42—H42	0.93

F2—P1—F5	178.6 (5)	N2—C11—H11A	109.6
F2—P1—F4	90.3 (4)	C8—C11—H11A	109.6
F5—P1—F4	90.4 (4)	N2—C11—H11B	109.6
F2—P1—F6	89.0 (4)	C8—C11—H11B	109.6
F5—P1—F6	92.3 (4)	H11A—C11—H11B	108.1
F4—P1—F6	91.1 (3)	C13—C12—N2	107.7 (4)
F2—P1—F3	91.1 (4)	C13—C12—H12	126.2
F5—P1—F3	87.6 (4)	N2—C12—H12	126.2
F4—P1—F3	90.6 (4)	C12—C13—N3	107.1 (4)
F6—P1—F3	178.3 (5)	C12—C13—H13	126.4
F2—P1—F1	89.4 (4)	N3—C13—H13	126.4
F5—P1—F1	89.9 (4)	N3—C14—N2	109.2 (3)
F4—P1—F1	179.8 (5)	N3—C14—H14	125.4
F6—P1—F1	89.0 (3)	N2—C14—H14	125.4
F3—P1—F1	89.4 (4)	N3—C15—C16	112.6 (4)
F2'—P1'—F5'	177.1 (11)	N3—C15—H15A	109.1
F2'—P1'—F4'	90.7 (9)	C16—C15—H15A	109.1
F5'—P1'—F4'	90.7 (8)	N3—C15—H15B	109.1
F2'—P1'—F6'	87.3 (8)	C16—C15—H15B	109.1
F5'—P1'—F6'	90.1 (8)	H15A—C15—H15B	107.8
F4'—P1'—F6'	89.6 (8)	C21—C16—C17	119.4 (5)
F2'—P1'—F3'	89.6 (9)	C21—C16—C15	120.3 (4)
F5'—P1'—F3'	92.9 (9)	C17—C16—C15	120.3 (4)
F4'—P1'—F3'	91.5 (9)	C16—C17—C18	120.8 (5)
F6'—P1'—F3'	176.7 (10)	C16—C17—H17	119.6
F2'—P1'—F1'	88.5 (8)	C18—C17—H17	119.6
F5'—P1'—F1'	90.1 (8)	C19—C18—C17	118.4 (6)
F4'—P1'—F1'	178.7 (10)	C19—C18—H18	120.8
F6'—P1'—F1'	91.3 (8)	C17—C18—H18	120.8
F3'—P1'—F1'	87.5 (9)	C20—C19—C18	120.2 (6)
F10—P2—F12	90.9 (4)	C20—C19—H19	119.9
F10—P2—F11	91.0 (4)	C18—C19—H19	119.9
F12—P2—F11	90.7 (4)	C19—C20—C21	121.2 (6)
F10—P2—F7	178.8 (5)	C19—C20—H20	119.4
F12—P2—F7	89.3 (4)	C21—C20—H20	119.4
F11—P2—F7	90.2 (4)	C20—C21—C16	120.0 (5)
F10—P2—F8	90.1 (4)	C20—C21—H21	120.0
F12—P2—F8	90.3 (4)	C16—C21—H21	120.0
F11—P2—F8	178.5 (5)	O2—C22—C23	124.3 (4)
F7—P2—F8	88.7 (3)	O2—C22—C30	115.1 (3)
F10—P2—F9	89.2 (4)	C23—C22—C30	120.6 (4)
F12—P2—F9	179.6 (5)	C22—C23—C24	119.5 (5)
F11—P2—F9	89.7 (4)	C22—C23—H23	120.2
F7—P2—F9	90.6 (4)	C24—C23—H23	120.2
F8—P2—F9	89.4 (4)	C25—C24—C23	121.3 (5)
F7'—P2'—F8'	90.6 (8)	C25—C24—H24	119.3
F7'—P2'—F10'	179.2 (10)	C23—C24—H24	119.3
F8'—P2'—F10'	90.1 (8)	C24—C25—C26	120.3 (5)
F7'—P2'—F11'	91.6 (8)	C24—C25—H25	119.8
F8'—P2'—F11'	176.9 (10)	C26—C25—H25	119.8
F10'—P2'—F11'	87.6 (8)	C27—C26—C30	116.8 (4)
F7'—P2'—F12'	88.1 (9)	C27—C26—C25	123.7 (5)
F8'—P2'—F12'	90.9 (9)	C30—C26—C25	119.5 (5)
F10'—P2'—F12'	92.3 (9)	C28—C27—C26	120.7 (5)
F11'—P2'—F12'	91.3 (9)	C28—C27—H27	119.6
F7'—P2'—F9'	88.6 (8)	C26—C27—H27	119.6
F8'—P2'—F9'	89.3 (8)	C27—C28—C29	118.7 (5)
F10'—P2'—F9'	91.0 (9)	C27—C28—H28	120.6
F11'—P2'—F9'	88.7 (9)	C29—C28—H28	120.6
F12'—P2'—F9'	176.7 (10)	N6—C29—C28	122.9 (4)
C1—O1—C10	117.5 (4)	N6—C29—C32	116.6 (4)
C22—O2—C31	117.4 (4)	C28—C29—C32	120.4 (4)
C8—N1—C9	118.1 (4)	N6—C30—C26	122.0 (4)
C14—N2—C12	107.8 (4)	N6—C30—C22	119.4 (4)
C14—N2—C11	124.9 (3)	C26—C30—C22	118.6 (4)
C12—N2—C11	127.3 (4)	O2—C31—H31A	109.5
C14—N3—C13	108.3 (4)	O2—C31—H31B	109.5
C14—N3—C15	125.9 (4)	H31A—C31—H31B	109.5
C13—N3—C15	125.7 (4)	O2—C31—H31C	109.5
C35—N4—C34	107.9 (4)	H31A—C31—H31C	109.5
C35—N4—C36	125.9 (4)	H31B—C31—H31C	109.5
C34—N4—C36	126.2 (4)	N5—C32—C29	111.9 (3)
C35—N5—C33	107.9 (4)	N5—C32—H32A	109.2
C35—N5—C32	125.4 (4)	C29—C32—H32A	109.2
C33—N5—C32	126.7 (4)	N5—C32—H32B	109.2
C29—N6—C30	118.8 (3)	C29—C32—H32B	109.2
O1—C1—C2	124.8 (5)	H32A—C32—H32B	107.9
O1—C1—C9	115.4 (4)	C34—C33—N5	107.6 (4)
C2—C1—C9	119.8 (5)	C34—C33—H33	126.2
C1—C2—C3	119.7 (5)	N5—C33—H33	126.2
C1—C2—H2	120.1	C33—C34—N4	107.5 (4)
C3—C2—H2	120.1	C33—C34—H34	126.3
C4—C3—C2	121.9 (5)	N4—C34—H34	126.3
C4—C3—H3	119.1	N5—C35—N4	109.0 (4)
C2—C3—H3	119.1	N5—C35—H35	125.5
C3—C4—C5	120.5 (5)	N4—C35—H35	125.5
C3—C4—H4	119.8	N4—C36—C37	113.2 (4)
C5—C4—H4	119.8	N4—C36—H36A	108.9
C6—C5—C9	117.6 (4)	C37—C36—H36A	108.9
C6—C5—C4	122.8 (5)	N4—C36—H36B	108.9
C9—C5—C4	119.6 (5)	C37—C36—H36B	108.9
C7—C6—C5	119.5 (5)	H36A—C36—H36B	107.8
C7—C6—H6	120.2	C42—C37—C38	117.2 (5)
C5—C6—H6	120.2	C42—C37—C36	121.3 (5)
C6—C7—C8	118.8 (5)	C38—C37—C36	121.5 (5)
C6—C7—H7	120.6	C37—C38—C39	120.9 (5)
C8—C7—H7	120.6	C37—C38—H38	119.5
N1—C8—C7	123.7 (4)	C39—C38—H38	119.5
N1—C8—C11	116.7 (4)	C40—C39—C38	119.4 (6)
C7—C8—C11	119.6 (4)	C40—C39—H39	120.3
N1—C9—C5	122.2 (4)	C38—C39—H39	120.3
N1—C9—C1	119.2 (4)	C39—C40—C41	121.6 (6)
C5—C9—C1	118.5 (4)	C39—C40—H40	119.2
O1—C10—H10A	109.5	C41—C40—H40	119.2
O1—C10—H10B	109.5	C40—C41—C42	118.3 (6)
H10A—C10—H10B	109.5	C40—C41—H41	120.8
O1—C10—H10C	109.5	C42—C41—H41	120.8
H10A—C10—H10C	109.5	C37—C42—C41	122.6 (5)
H10B—C10—H10C	109.5	C37—C42—H42	118.7
N2—C11—C8	110.1 (3)	C41—C42—H42	118.7

C10—O1—C1—C2	−3.3 (9)	C31—O2—C22—C23	3.0 (6)
C10—O1—C1—C9	176.6 (6)	C31—O2—C22—C30	−177.4 (4)
O1—C1—C2—C3	179.6 (5)	O2—C22—C23—C24	179.0 (4)
C9—C1—C2—C3	−0.3 (8)	C30—C22—C23—C24	−0.6 (6)
C1—C2—C3—C4	−0.7 (10)	C22—C23—C24—C25	0.1 (7)
C2—C3—C4—C5	1.5 (10)	C23—C24—C25—C26	0.7 (8)
C3—C4—C5—C6	−179.8 (6)	C24—C25—C26—C27	179.0 (5)
C3—C4—C5—C9	−1.1 (8)	C24—C25—C26—C30	−1.1 (7)
C9—C5—C6—C7	0.3 (7)	C30—C26—C27—C28	0.2 (7)
C4—C5—C6—C7	179.0 (5)	C25—C26—C27—C28	−179.9 (5)
C5—C6—C7—C8	1.1 (8)	C26—C27—C28—C29	−2.1 (8)
C9—N1—C8—C7	1.6 (6)	C30—N6—C29—C28	−0.2 (6)
C9—N1—C8—C11	−177.1 (3)	C30—N6—C29—C32	−178.9 (3)
C6—C7—C8—N1	−2.2 (7)	C27—C28—C29—N6	2.1 (7)
C6—C7—C8—C11	176.4 (4)	C27—C28—C29—C32	−179.2 (4)
C8—N1—C9—C5	0.0 (6)	C29—N6—C30—C26	−1.8 (5)
C8—N1—C9—C1	−179.7 (4)	C29—N6—C30—C22	179.4 (3)
C6—C5—C9—N1	−0.9 (7)	C27—C26—C30—N6	1.8 (6)
C4—C5—C9—N1	−179.6 (4)	C25—C26—C30—N6	−178.1 (4)
C6—C5—C9—C1	178.8 (4)	C27—C26—C30—C22	−179.5 (4)
C4—C5—C9—C1	0.1 (7)	C25—C26—C30—C22	0.6 (6)
O1—C1—C9—N1	0.4 (6)	O2—C22—C30—N6	−0.6 (5)
C2—C1—C9—N1	−179.7 (4)	C23—C22—C30—N6	179.0 (3)
O1—C1—C9—C5	−179.3 (4)	O2—C22—C30—C26	−179.4 (3)
C2—C1—C9—C5	0.6 (7)	C23—C22—C30—C26	0.2 (5)
C14—N2—C11—C8	−105.6 (4)	C35—N5—C32—C29	−111.9 (4)
C12—N2—C11—C8	71.5 (5)	C33—N5—C32—C29	66.0 (6)
N1—C8—C11—N2	86.3 (4)	N6—C29—C32—N5	59.0 (5)
C7—C8—C11—N2	−92.4 (5)	C28—C29—C32—N5	−119.7 (4)
C14—N2—C12—C13	−0.2 (5)	C35—N5—C33—C34	−0.5 (5)
C11—N2—C12—C13	−177.7 (4)	C32—N5—C33—C34	−178.7 (4)
N2—C12—C13—N3	0.1 (5)	N5—C33—C34—N4	0.2 (5)
C14—N3—C13—C12	0.1 (5)	C35—N4—C34—C33	0.2 (5)
C15—N3—C13—C12	−177.3 (4)	C36—N4—C34—C33	−177.6 (4)
C13—N3—C14—N2	−0.2 (5)	C33—N5—C35—N4	0.6 (5)
C15—N3—C14—N2	177.1 (3)	C32—N5—C35—N4	178.9 (3)
C12—N2—C14—N3	0.3 (5)	C34—N4—C35—N5	−0.5 (5)
C11—N2—C14—N3	177.8 (3)	C36—N4—C35—N5	177.3 (4)
C14—N3—C15—C16	−74.3 (5)	C35—N4—C36—C37	−98.1 (5)
C13—N3—C15—C16	102.6 (5)	C34—N4—C36—C37	79.4 (6)
N3—C15—C16—C21	104.4 (5)	N4—C36—C37—C42	84.1 (6)
N3—C15—C16—C17	−77.1 (6)	N4—C36—C37—C38	−97.9 (6)
C21—C16—C17—C18	−0.4 (8)	C42—C37—C38—C39	−0.3 (8)
C15—C16—C17—C18	−178.9 (5)	C36—C37—C38—C39	−178.5 (5)
C16—C17—C18—C19	−1.1 (10)	C37—C38—C39—C40	0.2 (9)
C17—C18—C19—C20	2.7 (11)	C38—C39—C40—C41	0.7 (10)
C18—C19—C20—C21	−3.0 (10)	C39—C40—C41—C42	−1.5 (11)
C19—C20—C21—C16	1.5 (9)	C38—C37—C42—C41	−0.5 (9)
C17—C16—C21—C20	0.2 (8)	C36—C37—C42—C41	177.7 (6)
C15—C16—C21—C20	178.7 (5)	C40—C41—C42—C37	1.4 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···F6ⁱ	0.97	2.53	3.071 (7)	115
C12—H12···F9ⁱⁱ	0.93	2.53	3.403 (11)	157
C13—H13···F9ⁱⁱⁱ	0.93	2.42	3.341 (11)	173
C14—H14···N1ⁱ	0.93	2.38	3.248 (5)	156
C15—H15A···F11ⁱⁱⁱ	0.97	2.39	3.314 (8)	159
C35—H35···N6^iv	0.93	2.42	3.343 (5)	174
C36—H36A···F8^v	0.97	2.52	3.217 (8)	129

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀N₃O⁺·F₆P⁻
M_r	475.37
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	12.272 (3), 12.537 (3), 14.361 (3)
α, β, γ (°)	90.847 (3), 91.539 (3), 93.809 (3)
V (Å³)	2203.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.49 × 0.45 × 0.43

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.911, 0.922
No. of measured, independent and observed [I > 2σ(I)] reflections	15491, 7961, 4602
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.215, 1.05
No. of reflections	7961
No. of parameters	708
No. of restraints	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.24

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···F6ⁱ	0.97	2.53	3.071 (7)	115
C12—H12···F9ⁱⁱ	0.93	2.53	3.403 (11)	157
C13—H13···F9ⁱⁱⁱ	0.93	2.42	3.341 (11)	173
C14—H14···N1ⁱ	0.93	2.38	3.248 (5)	156
C15—H15A···F11ⁱⁱⁱ	0.97	2.39	3.314 (8)	159
C35—H35···N6^iv	0.93	2.42	3.343 (5)	174
C36—H36A···F8^v	0.97	2.52	3.217 (8)	129

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

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