In the title compound, 6,16,38-triaza-3,13-diazonia-22,25,28,31-tetraoxaoctacyclo[30.2.2.2
18,21.1
3,6.1
8,12.1
13,16]hentetraconta-1(34),3,8,10,12(38),13,18,20,32,35,40-undecaene bis(hexafluorophosphate), C
33H
37N
5O
42+·2PF
6−, the two imidazolium rings adopt a
cis configuration with respect to the 2,6-dimethylpyridine group. The crystal packing is stabilized by C—H
F hydrogen bonds.
Supporting information
CCDC reference: 271836
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.056
- wR factor = 0.188
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C6
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
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 P1
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 30.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT432_ALERT_2_C Short Inter X...Y Contact F7 .. C7 .. 2.95 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); 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, 1999); software used to prepare material for publication: SHELXTL.
[(triglycol ditolylene)imidiazolium]-2,6-dimethylpyridine dihexaflourphosphate
top
Crystal data top
C33H37N5O42+·2PF6− | Z = 2 |
Mr = 857.62 | F(000) = 880 |
Triclinic, P1 | Dx = 1.518 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8299 (11) Å | Cell parameters from 3160 reflections |
b = 10.1415 (11) Å | θ = 2.2–21.9° |
c = 19.486 (2) Å | µ = 0.22 mm−1 |
α = 83.183 (2)° | T = 293 K |
β = 89.886 (2)° | Block, colourless |
γ = 76.646 (2)° | 0.32 × 0.24 × 0.22 mm |
V = 1876.0 (4) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 6554 independent reflections |
Radiation source: fine-focus sealed tube | 4429 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→9 |
Tmin = 0.922, Tmax = 0.953 | k = −12→12 |
10269 measured reflections | l = −23→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.1116P)2 + 0.2928P] where P = (Fo2 + 2Fc2)/3 |
6554 reflections | (Δ/σ)max = 0.001 |
560 parameters | Δρmax = 0.44 e Å−3 |
36 restraints | Δρmin = −0.24 e Å−3 |
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 | Uiso*/Ueq | Occ. (<1) |
N1 | 0.8929 (3) | 0.2473 (3) | 0.42984 (13) | 0.0624 (7) | |
N2 | 0.9898 (3) | 0.0614 (3) | 0.33474 (14) | 0.0668 (7) | |
N3 | 0.8242 (3) | 0.0532 (2) | 0.26587 (13) | 0.0579 (6) | |
N4 | 0.6163 (2) | 0.3856 (2) | 0.41431 (12) | 0.0557 (6) | |
N5 | 0.5182 (2) | 0.4530 (2) | 0.31403 (12) | 0.0540 (6) | |
O1 | 0.7479 (3) | −0.2455 (3) | 0.00620 (15) | 0.1012 (9) | |
O2 | 0.8459 (3) | −0.0946 (3) | −0.11471 (13) | 0.0815 (7) | |
O3 | 0.6904 (3) | 0.1869 (3) | −0.13918 (13) | 0.0872 (8) | |
O4 | 0.7282 (2) | 0.3329 (3) | 0.01401 (12) | 0.0756 (6) | |
C1 | 1.0311 (3) | 0.1908 (3) | 0.43089 (17) | 0.0669 (8) | |
C2 | 1.1210 (4) | 0.2059 (4) | 0.48126 (19) | 0.0782 (10) | |
H2 | 1.2148 | 0.1606 | 0.4821 | 0.094* | |
C3 | 1.0708 (4) | 0.2882 (4) | 0.5301 (2) | 0.0865 (11) | |
H3 | 1.1305 | 0.3020 | 0.5641 | 0.104* | |
C4 | 0.9322 (4) | 0.3505 (4) | 0.52882 (17) | 0.0742 (9) | |
H4 | 0.8964 | 0.4091 | 0.5611 | 0.089* | |
C5 | 0.8458 (3) | 0.3250 (3) | 0.47865 (15) | 0.0569 (7) | |
C6 | 1.0906 (4) | 0.1162 (5) | 0.3717 (2) | 0.0987 (14) | |
H6A | 1.1281 | 0.1778 | 0.3392 | 0.118* | |
H6B | 1.1677 | 0.0412 | 0.3892 | 0.118* | |
C7 | 0.8854 (3) | 0.1354 (3) | 0.29380 (18) | 0.0651 (8) | |
H7 | 0.8602 | 0.2303 | 0.2863 | 0.078* | |
C8 | 0.9937 (4) | −0.0712 (3) | 0.33173 (19) | 0.0741 (9) | |
H8 | 1.0569 | −0.1453 | 0.3553 | 0.089* | |
C9 | 0.8890 (4) | −0.0770 (3) | 0.28816 (19) | 0.0695 (9) | |
H9 | 0.8662 | −0.1553 | 0.2760 | 0.083* | |
C10 | 0.7036 (4) | 0.0957 (3) | 0.21728 (18) | 0.0711 (9) | |
H10A | 0.6946 | 0.1903 | 0.1984 | 0.085* | |
H10B | 0.6191 | 0.0893 | 0.2419 | 0.085* | |
C11 | 0.7184 (3) | 0.0091 (3) | 0.15932 (17) | 0.0636 (8) | |
C12 | 0.8186 (4) | 0.0122 (3) | 0.10996 (19) | 0.0704 (9) | |
H12 | 0.8772 | 0.0720 | 0.1114 | 0.084* | |
C13 | 0.8334 (4) | −0.0732 (4) | 0.05790 (18) | 0.0730 (9) | |
H13 | 0.9029 | −0.0721 | 0.0255 | 0.088* | |
C14 | 0.7454 (4) | −0.1576 (3) | 0.05501 (18) | 0.0713 (9) | |
C15 | 0.6427 (4) | −0.1587 (4) | 0.1024 (2) | 0.0861 (11) | |
H15 | 0.5810 | −0.2149 | 0.0994 | 0.103* | |
C16 | 0.6308 (4) | −0.0768 (4) | 0.15454 (19) | 0.0770 (10) | |
H16 | 0.5620 | −0.0797 | 0.1871 | 0.092* | |
C17 | 0.8734 (5) | −0.2900 (4) | −0.0312 (2) | 0.1022 (14) | |
H17A | 0.8988 | −0.3889 | −0.0269 | 0.123* | |
H17B | 0.9495 | −0.2590 | −0.0118 | 0.123* | |
C18 | 0.8502 (5) | −0.2334 (4) | −0.1062 (2) | 0.0940 (12) | |
H18A | 0.9253 | −0.2806 | −0.1330 | 0.113* | |
H18B | 0.7628 | −0.2483 | −0.1230 | 0.113* | |
C19 | 0.7830 (4) | −0.0318 (4) | −0.17801 (19) | 0.0895 (12) | |
H19A | 0.6883 | −0.0443 | −0.1804 | 0.107* | |
H19B | 0.8346 | −0.0744 | −0.2152 | 0.107* | |
C20 | 0.7799 (5) | 0.1152 (4) | −0.1869 (2) | 0.0947 (13) | |
H20A | 0.8739 | 0.1274 | −0.1806 | 0.114* | |
H20B | 0.7480 | 0.1537 | −0.2336 | 0.114* | |
C21 | 0.7605 (4) | 0.2303 (4) | −0.08833 (18) | 0.0803 (10) | |
H21A | 0.7971 | 0.3075 | −0.1074 | 0.096* | |
H21B | 0.8383 | 0.1574 | −0.0696 | 0.096* | |
C22 | 0.6587 (3) | 0.2712 (3) | −0.03205 (16) | 0.0651 (8) | |
H22A | 0.5747 | 0.3350 | −0.0516 | 0.078* | |
H22B | 0.6325 | 0.1916 | −0.0081 | 0.078* | |
C23 | 0.6585 (3) | 0.3791 (3) | 0.06976 (16) | 0.0610 (8) | |
C24 | 0.5254 (3) | 0.3643 (3) | 0.08657 (16) | 0.0596 (8) | |
H24 | 0.4775 | 0.3198 | 0.0592 | 0.072* | |
C25 | 0.4647 (3) | 0.4169 (3) | 0.14475 (16) | 0.0585 (7) | |
H25 | 0.3749 | 0.4084 | 0.1559 | 0.070* | |
C26 | 0.5349 (3) | 0.4817 (3) | 0.18654 (15) | 0.0557 (7) | |
C27 | 0.6668 (3) | 0.4945 (3) | 0.16909 (18) | 0.0679 (9) | |
H27 | 0.7150 | 0.5384 | 0.1966 | 0.081* | |
C28 | 0.7289 (3) | 0.4432 (3) | 0.11139 (18) | 0.0712 (9) | |
H28 | 0.8189 | 0.4519 | 0.1005 | 0.085* | |
C29 | 0.4672 (3) | 0.5417 (3) | 0.24877 (16) | 0.0651 (8) | |
H29A | 0.4868 | 0.6307 | 0.2505 | 0.078* | |
H29B | 0.3666 | 0.5541 | 0.2443 | 0.078* | |
C30 | 0.5966 (3) | 0.4831 (3) | 0.36221 (15) | 0.0560 (7) | |
H30 | 0.6321 | 0.5610 | 0.3596 | 0.067* | |
C31 | 0.5511 (4) | 0.2874 (3) | 0.39865 (19) | 0.0688 (9) | |
H31 | 0.5496 | 0.2063 | 0.4262 | 0.083* | |
C32 | 0.4899 (3) | 0.3299 (3) | 0.33629 (19) | 0.0671 (9) | |
H32 | 0.4375 | 0.2838 | 0.3124 | 0.081* | |
C33 | 0.6922 (3) | 0.3868 (4) | 0.47901 (16) | 0.0712 (9) | |
H33A | 0.6517 | 0.3377 | 0.5164 | 0.085* | |
H33B | 0.6786 | 0.4805 | 0.4887 | 0.085* | |
P1 | 0.49724 (8) | 0.87824 (8) | 0.38189 (4) | 0.0592 (3) | |
F1 | 0.6172 (2) | 0.9526 (2) | 0.39465 (15) | 0.1090 (8) | |
F2 | 0.5701 (2) | 0.7512 (2) | 0.43693 (11) | 0.0841 (6) | |
F3 | 0.4084 (3) | 0.9456 (3) | 0.44133 (12) | 0.1160 (9) | |
F4 | 0.4247 (2) | 1.0027 (2) | 0.32720 (12) | 0.0997 (7) | |
F5 | 0.5861 (3) | 0.8062 (2) | 0.32320 (11) | 0.0959 (7) | |
F6 | 0.3787 (2) | 0.8023 (3) | 0.36823 (12) | 0.1069 (8) | |
P2 | 0.03936 (9) | 0.51472 (9) | 0.27131 (5) | 0.0722 (3) | |
F7 | −0.0365 (9) | 0.3993 (7) | 0.2610 (5) | 0.140 (4) | 0.568 (15) |
F8 | −0.0894 (7) | 0.5912 (9) | 0.3099 (7) | 0.154 (5) | 0.568 (15) |
F9 | 0.1032 (12) | 0.4340 (8) | 0.3427 (3) | 0.137 (4) | 0.568 (15) |
F10 | 0.1742 (6) | 0.4386 (10) | 0.2368 (6) | 0.123 (4) | 0.568 (15) |
F11 | −0.0190 (13) | 0.5958 (11) | 0.2015 (5) | 0.170 (5) | 0.568 (15) |
F12 | 0.1150 (7) | 0.6334 (5) | 0.2832 (5) | 0.127 (4) | 0.568 (15) |
F7' | −0.0310 (8) | 0.4041 (7) | 0.2448 (6) | 0.089 (3) | 0.432 (15) |
F8' | −0.0417 (15) | 0.5053 (16) | 0.3400 (4) | 0.148 (5) | 0.432 (15) |
F9' | 0.1647 (9) | 0.4018 (8) | 0.3030 (10) | 0.165 (7) | 0.432 (15) |
F10' | 0.1181 (15) | 0.5246 (14) | 0.2013 (5) | 0.151 (5) | 0.432 (15) |
F11' | −0.0896 (10) | 0.6284 (5) | 0.2375 (7) | 0.115 (5) | 0.432 (15) |
F12' | 0.1054 (10) | 0.6272 (9) | 0.2971 (5) | 0.127 (5) | 0.432 (15) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0549 (15) | 0.0694 (16) | 0.0591 (16) | −0.0051 (12) | −0.0086 (12) | −0.0116 (13) |
N2 | 0.0564 (15) | 0.0686 (17) | 0.0733 (18) | −0.0009 (13) | 0.0041 (13) | −0.0268 (14) |
N3 | 0.0643 (15) | 0.0477 (13) | 0.0599 (15) | −0.0058 (11) | 0.0036 (12) | −0.0137 (11) |
N4 | 0.0546 (14) | 0.0559 (14) | 0.0511 (15) | 0.0004 (11) | −0.0002 (11) | −0.0112 (12) |
N5 | 0.0539 (13) | 0.0477 (13) | 0.0572 (15) | −0.0021 (10) | −0.0089 (11) | −0.0123 (11) |
O1 | 0.122 (2) | 0.112 (2) | 0.0847 (19) | −0.0457 (18) | 0.0121 (17) | −0.0379 (17) |
O2 | 0.0825 (16) | 0.0862 (17) | 0.0781 (17) | −0.0201 (13) | −0.0024 (13) | −0.0173 (13) |
O3 | 0.0831 (16) | 0.1041 (19) | 0.0680 (16) | 0.0004 (14) | 0.0118 (13) | −0.0286 (14) |
O4 | 0.0653 (14) | 0.0989 (17) | 0.0648 (15) | −0.0201 (12) | 0.0049 (11) | −0.0164 (13) |
C1 | 0.0602 (19) | 0.074 (2) | 0.065 (2) | −0.0103 (16) | −0.0014 (15) | −0.0137 (16) |
C2 | 0.060 (2) | 0.100 (3) | 0.071 (2) | −0.0114 (18) | −0.0191 (17) | −0.009 (2) |
C3 | 0.076 (2) | 0.116 (3) | 0.073 (2) | −0.030 (2) | −0.0185 (19) | −0.018 (2) |
C4 | 0.085 (2) | 0.084 (2) | 0.055 (2) | −0.0205 (19) | −0.0116 (17) | −0.0128 (17) |
C5 | 0.0668 (18) | 0.0573 (17) | 0.0433 (16) | −0.0102 (14) | −0.0005 (13) | −0.0015 (13) |
C6 | 0.0533 (19) | 0.127 (3) | 0.118 (3) | −0.003 (2) | −0.007 (2) | −0.063 (3) |
C7 | 0.0581 (18) | 0.0506 (17) | 0.085 (2) | −0.0037 (14) | 0.0001 (16) | −0.0190 (16) |
C8 | 0.073 (2) | 0.063 (2) | 0.074 (2) | 0.0036 (16) | −0.0026 (18) | 0.0033 (17) |
C9 | 0.079 (2) | 0.0451 (17) | 0.081 (2) | −0.0087 (15) | 0.0014 (18) | −0.0038 (15) |
C10 | 0.068 (2) | 0.067 (2) | 0.072 (2) | 0.0020 (16) | −0.0106 (16) | −0.0189 (17) |
C11 | 0.0579 (18) | 0.0642 (19) | 0.064 (2) | −0.0042 (15) | −0.0060 (15) | −0.0079 (15) |
C12 | 0.067 (2) | 0.065 (2) | 0.083 (2) | −0.0237 (16) | −0.0021 (18) | −0.0061 (18) |
C13 | 0.073 (2) | 0.077 (2) | 0.070 (2) | −0.0185 (18) | 0.0134 (17) | −0.0116 (18) |
C14 | 0.084 (2) | 0.070 (2) | 0.066 (2) | −0.0266 (18) | 0.0003 (18) | −0.0139 (17) |
C15 | 0.085 (3) | 0.108 (3) | 0.081 (3) | −0.047 (2) | 0.008 (2) | −0.027 (2) |
C16 | 0.071 (2) | 0.094 (3) | 0.075 (2) | −0.0306 (19) | 0.0117 (17) | −0.022 (2) |
C17 | 0.131 (4) | 0.080 (3) | 0.088 (3) | −0.005 (2) | 0.012 (3) | −0.024 (2) |
C18 | 0.120 (3) | 0.091 (3) | 0.077 (3) | −0.026 (2) | 0.012 (2) | −0.027 (2) |
C19 | 0.085 (3) | 0.117 (3) | 0.055 (2) | 0.006 (2) | 0.0004 (18) | −0.028 (2) |
C20 | 0.104 (3) | 0.100 (3) | 0.065 (2) | 0.010 (2) | 0.023 (2) | −0.015 (2) |
C21 | 0.071 (2) | 0.098 (3) | 0.064 (2) | −0.0029 (19) | 0.0041 (17) | −0.009 (2) |
C22 | 0.0625 (19) | 0.074 (2) | 0.0549 (19) | −0.0072 (16) | −0.0005 (15) | −0.0081 (16) |
C23 | 0.0628 (19) | 0.0622 (18) | 0.0521 (18) | −0.0041 (14) | 0.0010 (14) | −0.0035 (14) |
C24 | 0.0578 (18) | 0.0633 (18) | 0.0578 (19) | −0.0119 (14) | −0.0092 (14) | −0.0119 (15) |
C25 | 0.0518 (16) | 0.0618 (18) | 0.0595 (19) | −0.0077 (14) | −0.0079 (14) | −0.0083 (15) |
C26 | 0.0561 (17) | 0.0490 (15) | 0.0569 (18) | −0.0034 (13) | −0.0160 (13) | −0.0037 (13) |
C27 | 0.067 (2) | 0.068 (2) | 0.072 (2) | −0.0214 (16) | −0.0161 (17) | −0.0116 (17) |
C28 | 0.0581 (19) | 0.082 (2) | 0.077 (2) | −0.0254 (17) | −0.0084 (16) | −0.0054 (19) |
C29 | 0.071 (2) | 0.0548 (17) | 0.062 (2) | 0.0033 (15) | −0.0196 (16) | −0.0122 (15) |
C30 | 0.0617 (17) | 0.0459 (15) | 0.0584 (19) | −0.0061 (13) | −0.0078 (14) | −0.0110 (14) |
C31 | 0.072 (2) | 0.0599 (19) | 0.073 (2) | −0.0140 (16) | 0.0082 (17) | −0.0054 (16) |
C32 | 0.066 (2) | 0.0621 (19) | 0.079 (2) | −0.0226 (16) | 0.0008 (17) | −0.0156 (17) |
C33 | 0.073 (2) | 0.083 (2) | 0.0483 (18) | 0.0008 (17) | −0.0064 (15) | −0.0102 (16) |
P1 | 0.0555 (5) | 0.0630 (5) | 0.0568 (5) | −0.0042 (4) | 0.0004 (4) | −0.0163 (4) |
F1 | 0.0978 (16) | 0.0868 (15) | 0.151 (2) | −0.0329 (13) | −0.0235 (15) | −0.0253 (15) |
F2 | 0.0806 (13) | 0.0827 (13) | 0.0779 (14) | −0.0003 (10) | −0.0078 (10) | −0.0013 (10) |
F3 | 0.1094 (18) | 0.135 (2) | 0.0806 (15) | 0.0316 (15) | 0.0134 (13) | −0.0412 (15) |
F4 | 0.1029 (16) | 0.0880 (15) | 0.0910 (16) | 0.0021 (12) | −0.0125 (13) | 0.0101 (12) |
F5 | 0.1214 (18) | 0.0811 (13) | 0.0854 (15) | −0.0160 (12) | 0.0406 (13) | −0.0275 (12) |
F6 | 0.0919 (16) | 0.146 (2) | 0.0953 (17) | −0.0607 (15) | −0.0168 (13) | −0.0008 (15) |
P2 | 0.0632 (5) | 0.0685 (6) | 0.0899 (7) | −0.0194 (4) | 0.0008 (5) | −0.0218 (5) |
F7 | 0.151 (8) | 0.105 (6) | 0.183 (8) | −0.074 (6) | −0.054 (6) | 0.001 (5) |
F8 | 0.101 (4) | 0.112 (6) | 0.252 (13) | −0.011 (4) | 0.071 (6) | −0.062 (7) |
F9 | 0.201 (12) | 0.112 (5) | 0.095 (5) | −0.035 (6) | −0.043 (5) | −0.003 (3) |
F10 | 0.085 (4) | 0.152 (8) | 0.151 (8) | −0.029 (4) | 0.033 (5) | −0.094 (7) |
F11 | 0.185 (11) | 0.198 (9) | 0.125 (6) | −0.079 (9) | −0.041 (7) | 0.053 (6) |
F12 | 0.091 (5) | 0.069 (4) | 0.236 (10) | −0.037 (3) | 0.005 (5) | −0.044 (4) |
F7' | 0.078 (5) | 0.067 (5) | 0.128 (6) | −0.017 (4) | −0.009 (4) | −0.040 (4) |
F8' | 0.181 (12) | 0.161 (11) | 0.114 (7) | −0.058 (10) | 0.045 (7) | −0.026 (7) |
F9' | 0.089 (7) | 0.113 (6) | 0.28 (2) | −0.002 (5) | −0.069 (10) | 0.001 (11) |
F10' | 0.172 (13) | 0.168 (10) | 0.127 (8) | −0.062 (10) | 0.051 (8) | −0.026 (7) |
F11' | 0.105 (6) | 0.055 (3) | 0.184 (12) | −0.015 (3) | −0.058 (6) | −0.016 (5) |
F12' | 0.161 (11) | 0.157 (11) | 0.090 (6) | −0.069 (8) | −0.013 (5) | −0.056 (6) |
Geometric parameters (Å, º) top
N1—C5 | 1.322 (4) | C17—H17A | 0.97 |
N1—C1 | 1.346 (4) | C17—H17B | 0.97 |
N2—C7 | 1.326 (4) | C18—H18A | 0.97 |
N2—C8 | 1.345 (4) | C18—H18B | 0.97 |
N2—C6 | 1.471 (4) | C19—C20 | 1.474 (6) |
N3—C7 | 1.302 (4) | C19—H19A | 0.97 |
N3—C9 | 1.346 (4) | C19—H19B | 0.97 |
N3—C10 | 1.470 (4) | C20—H20A | 0.97 |
N4—C30 | 1.312 (4) | C20—H20B | 0.97 |
N4—C31 | 1.365 (4) | C21—C22 | 1.513 (4) |
N4—C33 | 1.469 (4) | C21—H21A | 0.97 |
N5—C30 | 1.322 (3) | C21—H21B | 0.97 |
N5—C32 | 1.363 (4) | C22—H22A | 0.97 |
N5—C29 | 1.483 (4) | C22—H22B | 0.97 |
O1—C14 | 1.376 (4) | C23—C28 | 1.377 (4) |
O1—C17 | 1.440 (5) | C23—C24 | 1.385 (4) |
O2—C18 | 1.388 (5) | C24—C25 | 1.385 (4) |
O2—C19 | 1.394 (4) | C24—H24 | 0.93 |
O3—C21 | 1.377 (4) | C25—C26 | 1.382 (4) |
O3—C20 | 1.424 (4) | C25—H25 | 0.93 |
O4—C23 | 1.356 (4) | C26—C27 | 1.371 (4) |
O4—C22 | 1.414 (4) | C26—C29 | 1.506 (4) |
C1—C2 | 1.367 (4) | C27—C28 | 1.377 (5) |
C1—C6 | 1.498 (5) | C27—H27 | 0.93 |
C2—C3 | 1.357 (5) | C28—H28 | 0.93 |
C2—H2 | 0.93 | C29—H29A | 0.97 |
C3—C4 | 1.362 (5) | C29—H29B | 0.97 |
C3—H3 | 0.93 | C30—H30 | 0.93 |
C4—C5 | 1.382 (4) | C31—C32 | 1.335 (5) |
C4—H4 | 0.93 | C31—H31 | 0.93 |
C5—C33 | 1.496 (4) | C32—H32 | 0.93 |
C6—H6A | 0.97 | C33—H33A | 0.97 |
C6—H6B | 0.97 | C33—H33B | 0.97 |
C7—H7 | 0.93 | P1—F1 | 1.574 (2) |
C8—C9 | 1.352 (5) | P1—F3 | 1.575 (2) |
C8—H8 | 0.93 | P1—F6 | 1.577 (2) |
C9—H9 | 0.93 | P1—F5 | 1.582 (2) |
C10—C11 | 1.498 (4) | P1—F4 | 1.583 (2) |
C10—H10A | 0.97 | P1—F2 | 1.604 (2) |
C10—H10B | 0.97 | P2—F11 | 1.541 (5) |
C11—C16 | 1.369 (4) | P2—F9' | 1.547 (6) |
C11—C12 | 1.379 (5) | P2—F7 | 1.558 (5) |
C12—C13 | 1.396 (5) | P2—F8' | 1.561 (6) |
C12—H12 | 0.93 | P2—F8 | 1.565 (5) |
C13—C14 | 1.356 (5) | P2—F10 | 1.566 (4) |
C13—H13 | 0.93 | P2—F12' | 1.566 (6) |
C14—C15 | 1.368 (5) | P2—F10' | 1.571 (6) |
C15—C16 | 1.375 (5) | P2—F9 | 1.580 (5) |
C15—H15 | 0.93 | P2—F7' | 1.581 (6) |
C16—H16 | 0.93 | P2—F11' | 1.586 (5) |
C17—C18 | 1.503 (6) | P2—F12 | 1.593 (4) |
| | | |
C5—N1—C1 | 117.2 (3) | O3—C21—H21A | 110.1 |
C7—N2—C8 | 108.1 (3) | C22—C21—H21A | 110.1 |
C7—N2—C6 | 125.3 (3) | O3—C21—H21B | 110.1 |
C8—N2—C6 | 126.4 (3) | C22—C21—H21B | 110.1 |
C7—N3—C9 | 109.4 (3) | H21A—C21—H21B | 108.4 |
C7—N3—C10 | 125.3 (3) | O4—C22—C21 | 106.5 (3) |
C9—N3—C10 | 125.2 (3) | O4—C22—H22A | 110.4 |
C30—N4—C31 | 108.5 (3) | C21—C22—H22A | 110.4 |
C30—N4—C33 | 124.7 (3) | O4—C22—H22B | 110.4 |
C31—N4—C33 | 126.8 (3) | C21—C22—H22B | 110.4 |
C30—N5—C32 | 107.9 (3) | H22A—C22—H22B | 108.6 |
C30—N5—C29 | 125.2 (2) | O4—C23—C28 | 115.8 (3) |
C32—N5—C29 | 126.9 (3) | O4—C23—C24 | 124.4 (3) |
C14—O1—C17 | 120.1 (3) | C28—C23—C24 | 119.8 (3) |
C18—O2—C19 | 111.3 (3) | C25—C24—C23 | 118.9 (3) |
C21—O3—C20 | 113.9 (3) | C25—C24—H24 | 120.5 |
C23—O4—C22 | 118.2 (2) | C23—C24—H24 | 120.5 |
N1—C1—C2 | 122.9 (3) | C26—C25—C24 | 121.4 (3) |
N1—C1—C6 | 118.6 (3) | C26—C25—H25 | 119.3 |
C2—C1—C6 | 118.4 (3) | C24—C25—H25 | 119.3 |
C3—C2—C1 | 118.8 (3) | C27—C26—C25 | 118.6 (3) |
C3—C2—H2 | 120.6 | C27—C26—C29 | 120.2 (3) |
C1—C2—H2 | 120.6 | C25—C26—C29 | 121.2 (3) |
C2—C3—C4 | 119.4 (3) | C26—C27—C28 | 120.9 (3) |
C2—C3—H3 | 120.3 | C26—C27—H27 | 119.5 |
C4—C3—H3 | 120.3 | C28—C27—H27 | 119.5 |
C3—C4—C5 | 118.8 (3) | C23—C28—C27 | 120.3 (3) |
C3—C4—H4 | 120.6 | C23—C28—H28 | 119.9 |
C5—C4—H4 | 120.6 | C27—C28—H28 | 119.9 |
N1—C5—C4 | 122.8 (3) | N5—C29—C26 | 111.9 (2) |
N1—C5—C33 | 117.9 (3) | N5—C29—H29A | 109.2 |
C4—C5—C33 | 119.3 (3) | C26—C29—H29A | 109.2 |
N2—C6—C1 | 114.5 (3) | N5—C29—H29B | 109.2 |
N2—C6—H6A | 108.6 | C26—C29—H29B | 109.2 |
C1—C6—H6A | 108.6 | H29A—C29—H29B | 107.9 |
N2—C6—H6B | 108.6 | N4—C30—N5 | 109.0 (3) |
C1—C6—H6B | 108.6 | N4—C30—H30 | 125.5 |
H6A—C6—H6B | 107.6 | N5—C30—H30 | 125.5 |
N3—C7—N2 | 108.6 (3) | C32—C31—N4 | 107.0 (3) |
N3—C7—H7 | 125.7 | C32—C31—H31 | 126.5 |
N2—C7—H7 | 125.7 | N4—C31—H31 | 126.5 |
N2—C8—C9 | 107.4 (3) | C31—C32—N5 | 107.6 (3) |
N2—C8—H8 | 126.3 | C31—C32—H32 | 126.2 |
C9—C8—H8 | 126.3 | N5—C32—H32 | 126.2 |
N3—C9—C8 | 106.4 (3) | N4—C33—C5 | 114.7 (3) |
N3—C9—H9 | 126.8 | N4—C33—H33A | 108.6 |
C8—C9—H9 | 126.8 | C5—C33—H33A | 108.6 |
N3—C10—C11 | 111.8 (2) | N4—C33—H33B | 108.6 |
N3—C10—H10A | 109.3 | C5—C33—H33B | 108.6 |
C11—C10—H10A | 109.3 | H33A—C33—H33B | 107.6 |
N3—C10—H10B | 109.3 | F1—P1—F3 | 91.53 (15) |
C11—C10—H10B | 109.3 | F1—P1—F6 | 179.03 (15) |
H10A—C10—H10B | 107.9 | F3—P1—F6 | 89.42 (15) |
C16—C11—C12 | 118.2 (3) | F1—P1—F5 | 89.49 (14) |
C16—C11—C10 | 119.8 (3) | F3—P1—F5 | 178.31 (14) |
C12—C11—C10 | 122.1 (3) | F6—P1—F5 | 89.55 (14) |
C11—C12—C13 | 120.9 (3) | F1—P1—F4 | 89.88 (14) |
C11—C12—H12 | 119.6 | F3—P1—F4 | 90.66 (13) |
C13—C12—H12 | 119.6 | F6—P1—F4 | 90.25 (13) |
C14—C13—C12 | 119.3 (3) | F5—P1—F4 | 90.69 (13) |
C14—C13—H13 | 120.3 | F1—P1—F2 | 90.57 (13) |
C12—C13—H13 | 120.3 | F3—P1—F2 | 89.58 (12) |
C13—C14—C15 | 120.4 (3) | F6—P1—F2 | 89.29 (13) |
C13—C14—O1 | 125.2 (3) | F5—P1—F2 | 89.07 (12) |
C15—C14—O1 | 114.5 (3) | F4—P1—F2 | 179.48 (13) |
C14—C15—C16 | 120.0 (3) | F11—P2—F7 | 91.8 (4) |
C14—C15—H15 | 120.0 | F9'—P2—F7 | 87.6 (5) |
C16—C15—H15 | 120.0 | F9'—P2—F8' | 91.1 (4) |
C11—C16—C15 | 121.2 (3) | F11—P2—F8 | 91.2 (4) |
C11—C16—H16 | 119.4 | F7—P2—F8 | 90.7 (3) |
C15—C16—H16 | 119.4 | F11—P2—F10 | 91.7 (4) |
O1—C17—C18 | 109.9 (4) | F7—P2—F10 | 91.5 (3) |
O1—C17—H17A | 109.7 | F8—P2—F10 | 176.3 (4) |
C18—C17—H17A | 109.7 | F9'—P2—F12' | 90.6 (4) |
O1—C17—H17B | 109.7 | F8'—P2—F12' | 90.1 (4) |
C18—C17—H17B | 109.7 | F9'—P2—F10' | 89.8 (4) |
H17A—C17—H17B | 108.2 | F8'—P2—F10' | 178.8 (5) |
O2—C18—C17 | 110.4 (3) | F12'—P2—F10' | 90.6 (4) |
O2—C18—H18A | 109.6 | F11—P2—F9 | 178.2 (4) |
C17—C18—H18A | 109.6 | F7—P2—F9 | 89.8 (4) |
O2—C18—H18B | 109.6 | F8—P2—F9 | 89.5 (4) |
C17—C18—H18B | 109.6 | F10—P2—F9 | 87.6 (3) |
H18A—C18—H18B | 108.1 | F9'—P2—F7' | 90.9 (4) |
O2—C19—C20 | 110.9 (3) | F8'—P2—F7' | 89.6 (4) |
O2—C19—H19A | 109.5 | F12'—P2—F7' | 178.5 (5) |
C20—C19—H19A | 109.5 | F10'—P2—F7' | 89.6 (4) |
O2—C19—H19B | 109.5 | F9'—P2—F11' | 178.7 (5) |
C20—C19—H19B | 109.5 | F8'—P2—F11' | 89.5 (4) |
H19A—C19—H19B | 108.0 | F12'—P2—F11' | 90.5 (4) |
O3—C20—C19 | 112.2 (3) | F10'—P2—F11' | 89.6 (4) |
O3—C20—H20A | 109.2 | F7'—P2—F11' | 88.0 (3) |
C19—C20—H20A | 109.2 | F11—P2—F12 | 88.7 (3) |
O3—C20—H20B | 109.2 | F7—P2—F12 | 178.8 (4) |
C19—C20—H20B | 109.2 | F8—P2—F12 | 88.2 (3) |
H20A—C20—H20B | 107.9 | F10—P2—F12 | 89.6 (3) |
O3—C21—C22 | 108.1 (3) | F9—P2—F12 | 89.6 (4) |
| | | |
C5—N1—C1—C2 | 2.9 (5) | C14—O1—C17—C18 | −113.1 (4) |
C5—N1—C1—C6 | −172.8 (3) | C19—O2—C18—C17 | −161.6 (4) |
N1—C1—C2—C3 | −4.2 (6) | O1—C17—C18—O2 | 73.2 (4) |
C6—C1—C2—C3 | 171.5 (4) | C18—O2—C19—C20 | −179.6 (3) |
C1—C2—C3—C4 | 1.8 (6) | C21—O3—C20—C19 | 108.8 (4) |
C2—C3—C4—C5 | 1.7 (6) | O2—C19—C20—O3 | −66.8 (4) |
C1—N1—C5—C4 | 0.8 (5) | C20—O3—C21—C22 | −165.7 (3) |
C1—N1—C5—C33 | −179.0 (3) | C23—O4—C22—C21 | −180.0 (3) |
C3—C4—C5—N1 | −3.1 (5) | O3—C21—C22—O4 | −171.8 (3) |
C3—C4—C5—C33 | 176.7 (3) | C22—O4—C23—C28 | −177.5 (3) |
C7—N2—C6—C1 | 71.3 (5) | C22—O4—C23—C24 | 3.1 (4) |
C8—N2—C6—C1 | −114.6 (4) | O4—C23—C24—C25 | −179.5 (3) |
N1—C1—C6—N2 | −25.3 (5) | C28—C23—C24—C25 | 1.1 (5) |
C2—C1—C6—N2 | 158.9 (4) | C23—C24—C25—C26 | −0.9 (4) |
C9—N3—C7—N2 | −0.3 (4) | C24—C25—C26—C27 | 0.5 (4) |
C10—N3—C7—N2 | 180.0 (3) | C24—C25—C26—C29 | 178.5 (3) |
C8—N2—C7—N3 | 0.3 (4) | C25—C26—C27—C28 | −0.4 (5) |
C6—N2—C7—N3 | 175.3 (3) | C29—C26—C27—C28 | −178.4 (3) |
C7—N2—C8—C9 | −0.2 (4) | O4—C23—C28—C27 | 179.6 (3) |
C6—N2—C8—C9 | −175.1 (3) | C24—C23—C28—C27 | −1.0 (5) |
C7—N3—C9—C8 | 0.2 (4) | C26—C27—C28—C23 | 0.6 (5) |
C10—N3—C9—C8 | 179.9 (3) | C30—N5—C29—C26 | 111.7 (3) |
N2—C8—C9—N3 | 0.0 (4) | C32—N5—C29—C26 | −70.7 (4) |
C7—N3—C10—C11 | 138.4 (3) | C27—C26—C29—N5 | −79.9 (4) |
C9—N3—C10—C11 | −41.2 (5) | C25—C26—C29—N5 | 102.2 (3) |
N3—C10—C11—C16 | 112.1 (4) | C31—N4—C30—N5 | 1.4 (3) |
N3—C10—C11—C12 | −67.7 (4) | C33—N4—C30—N5 | −176.7 (2) |
C16—C11—C12—C13 | −2.1 (5) | C32—N5—C30—N4 | −1.3 (3) |
C10—C11—C12—C13 | 177.7 (3) | C29—N5—C30—N4 | 176.7 (2) |
C11—C12—C13—C14 | 1.7 (5) | C30—N4—C31—C32 | −1.0 (3) |
C12—C13—C14—C15 | 0.3 (6) | C33—N4—C31—C32 | 177.1 (3) |
C12—C13—C14—O1 | 179.4 (3) | N4—C31—C32—N5 | 0.2 (4) |
C17—O1—C14—C13 | 22.0 (6) | C30—N5—C32—C31 | 0.6 (3) |
C17—O1—C14—C15 | −158.8 (4) | C29—N5—C32—C31 | −177.3 (3) |
C13—C14—C15—C16 | −1.8 (6) | C30—N4—C33—C5 | −89.8 (4) |
O1—C14—C15—C16 | 179.0 (4) | C31—N4—C33—C5 | 92.4 (4) |
C12—C11—C16—C15 | 0.5 (6) | N1—C5—C33—N4 | −16.3 (4) |
C10—C11—C16—C15 | −179.2 (3) | C4—C5—C33—N4 | 163.9 (3) |
C14—C15—C16—C11 | 1.4 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6B···F3i | 0.97 | 2.51 | 3.399 (5) | 153 |
C7—H7···F7ii | 0.93 | 2.19 | 2.949 (7) | 138 |
C9—H9···F8i | 0.93 | 2.51 | 3.299 (9) | 142 |
C25—H25···F10 | 0.93 | 2.51 | 3.347 (9) | 150 |
C29—H29B···F10 | 0.97 | 2.46 | 3.301 (7) | 145 |
C30—H30···F5 | 0.93 | 2.44 | 3.252 (4) | 146 |
Symmetry codes: (i) x+1, y−1, z; (ii) x+1, y, z. |