Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038767/ci2422sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038767/ci2422Isup2.hkl |
CCDC reference: 660272
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).
Both hexafluorophosphate ions were found to be disordered over two positions, with refined site occupancies of 0.742 (10) and 0.258 (10) [P1,F1–F6/P1',F1'–F6'] or 0.739 (19) and 0.261 (19) [P2,F7–F12/P2',F2'–F12']. The P—F and F···F distances were restrained to 1.57 (1) and 2.21 (2) Å, and the displacement parameters of all disordered atoms were restrained to an approximate isotropic behaviour. H atoms were positioned geometrically, with C—H = 0.93, 0.96 and 0.97 Å for aromatic, methyl and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
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.
For general background, see: Herrmann (2002); Herrmann & Kocher (1997). For synthesis, see: Lee et al. (2004).
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.
C21H20N3O+·F6P− | Z = 4 |
Mr = 475.37 | F(000) = 976 |
Triclinic, P1 | Dx = 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 |
Bruker SMART CCD area-detector diffractometer | 7961 independent reflections |
Radiation source: fine-focus sealed tube | 4602 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 25.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −14→14 |
Tmin = 0.911, Tmax = 0.922 | k = −15→15 |
15491 measured reflections | l = −17→17 |
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(Fo2) + (0.0928P)2 + 1.4093P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
7961 reflections | Δρmax = 0.50 e Å−3 |
708 parameters | Δρmin = −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) |
C21H20N3O+·F6P− | γ = 93.809 (3)° |
Mr = 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)° |
Bruker SMART CCD area-detector diffractometer | 7961 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 4602 reflections with I > 2σ(I) |
Tmin = 0.911, Tmax = 0.922 | Rint = 0.038 |
15491 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 240 restraints |
wR(F2) = 0.215 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.50 e Å−3 |
7961 reflections | Δρmin = −0.24 e Å−3 |
708 parameters |
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. |
x | y | z | Uiso*/Ueq | 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* |
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) |
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) |
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···N6iv | 0.93 | 2.42 | 3.343 (5) | 174 |
C36—H36A···F8v | 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− |
Mr | 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) |
Tmin, Tmax | 0.911, 0.922 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15491, 7961, 4602 |
Rint | 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 |
Δρmax, Δρmin (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.
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···N6iv | 0.93 | 2.42 | 3.343 (5) | 174 |
C36—H36A···F8v | 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. |
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.