3(5,10)-Anthracena-7(1,3)-benzena-1,5(1,3)-diimidazolacyclo­octa­phane-1,3-diium bis(hexa­fluoro­phosphate) acetonitrile tris­olvate

Qin, D.-B.; Jin, L.-H.; Gu, S.-J.; zhang, H.-X.

doi:10.1107/S1600536806033216

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3(5,10)-Anthracena-7(1,3)-benzena-1,5(1,3)-diimidazolacyclooctaphane-1,3-diium bis(hexafluorophosphate) acetonitrile trisolvate

D.-B. Qin, L.-H. Jin, S.-J. Gu and H.-X. zhang

In the title compound, C₃₀H₂₆N₄²⁺·2PF₆⁻·3CH₃CN, the two imidazolium rings in the cation adopt a syn configuration with respect to the anthracene group. The crystal packing shows weak intermolecular C—H

N hydrogen bonds between the cations and acetonitrile molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033216/cv2098sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033216/cv2098Isup2.hkl Contains datablock I

CCDC reference: 620948

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.001 Å
Disorder in solvent or counterion
R factor = 0.054
wR factor = 0.179
Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C30
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        C31
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C33
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C35
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      34.00 Perc.
PLAT410_ALERT_2_C Short Intra H...H Contact  H15B   ..  H28     ..       1.90 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H25    ..  H30A    ..       1.92 Ang.
PLAT737_ALERT_1_C D...A   Calc  3.4072(13), Rep    3.407(3) ......       2.31 su-Ra
              C1   -N5      1.555   1.555
PLAT737_ALERT_1_C D...A   Calc  3.3874(13), Rep    3.387(3) ......       2.31 su-Ra
              C14  -N5      1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      24.40 Deg.
              F1'  -P1   -F1      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      19.40 Deg.
              F5   -P1   -F5'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.85 Deg.
              F4   -P1   -F4'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      38.53 Deg.
              F3   -P1   -F3'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.53 Deg.
              F2'  -P1   -F2      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.28 Deg.
              F6'  -P1   -F6      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.07 Deg.
              F9   -P2   -F9'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      15.10 Deg.
              F10' -P2   -F10     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.50 Deg.
              F11  -P2   -F11'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      32.32 Deg.
              F7   -P2   -F7'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      23.84 Deg.
              F8   -P2   -F8'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      29.09 Deg.
              F12' -P2   -F12     1.555   1.555   1.555

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  17 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

3(5,10)-Anthracena-7(1,3)-benzena-1,5(1,3)-diimidazolacyclooctaphane-1,3-diium dihexafluorophosphate acetonitrile trisolvate top

Crystal data top

C₃₀H₂₆N₄²⁺·2PF₆⁻·3C₂H₃N	F(000) = 1752
M_r = 855.65	D_x = 1.415 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.643 (2) Å	Cell parameters from 3267 reflections
b = 22.391 (6) Å	θ = 2.6–21.1°
c = 20.983 (5) Å	µ = 0.20 mm⁻¹
β = 98.506 (5)°	T = 294 K
V = 4015.9 (18) Å³	Block, yellow
Z = 4	0.40 × 0.22 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	7086 independent reflections
Radiation source: fine-focus sealed tube	3197 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
φ and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.949, T_max = 0.965	k = −26→25
20280 measured reflections	l = −24→16

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0813P)² + 0.3116P] where P = (F_o² + 2F_c²)/3
7086 reflections	(Δ/σ)_max = 0.005
627 parameters	Δρ_max = 0.26 e Å⁻³
282 restraints	Δρ_min = −0.23 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	U_iso*/U_eq	Occ. (<1)
N1	0.31769 (5)	0.20021 (2)	0.76432 (2)	0.05763 (17)
N2	0.06948 (5)	0.20296 (2)	0.76325 (2)	0.06008 (17)
N3	0.04000 (5)	0.47948 (2)	0.75493 (2)	0.06113 (18)
N4	0.28406 (5)	0.489922 (19)	0.75031 (2)	0.05270 (16)
C1	0.18940 (6)	0.23054 (3)	0.74398 (3)	0.0598 (2)
H1	0.1841	0.2656	0.7200	0.072*
C2	0.27765 (8)	0.15102 (3)	0.79687 (3)	0.0719 (2)
H2	0.3455	0.1217	0.8158	0.086*
C3	0.12416 (8)	0.15290 (3)	0.79641 (3)	0.0700 (2)
H3	0.0646	0.1252	0.8152	0.084*
C4	−0.09118 (7)	0.22742 (3)	0.75532 (3)	0.0740 (3)
H4A	−0.1600	0.1992	0.7722	0.089*
H4B	−0.1289	0.2332	0.7099	0.089*
C5	−0.09480 (6)	0.28581 (3)	0.79008 (3)	0.0613 (2)
C6	−0.07709 (9)	0.28737 (3)	0.85588 (3)	0.0919 (3)
H6	−0.0683	0.2519	0.8793	0.110*
C7	−0.07226 (11)	0.34103 (3)	0.88741 (4)	0.1172 (4)
H7	−0.0594	0.3417	0.9322	0.141*
C8	−0.08601 (9)	0.39382 (3)	0.85398 (3)	0.0959 (3)
H8	−0.0828	0.4299	0.8761	0.115*
C9	−0.10452 (7)	0.39349 (3)	0.78793 (3)	0.0639 (2)
C10	−0.10949 (6)	0.33929 (3)	0.75669 (3)	0.0600 (2)
H10	−0.1231	0.3386	0.7119	0.072*
C11	−0.11519 (7)	0.45062 (3)	0.74997 (4)	0.0784 (3)
H11A	−0.1542	0.4422	0.7051	0.094*
H11B	−0.1882	0.4775	0.7662	0.094*
C12	0.08681 (7)	0.53064 (3)	0.78782 (3)	0.0683 (2)
H12	0.0245	0.5561	0.8082	0.082*
C13	0.23964 (7)	0.53701 (3)	0.78499 (3)	0.0645 (2)
H13	0.3038	0.5678	0.8032	0.077*
C14	0.16111 (6)	0.45565 (3)	0.73253 (3)	0.0584 (2)
H14	0.1599	0.4208	0.7084	0.070*
C15	0.44488 (6)	0.47660 (2)	0.73930 (3)	0.0594 (2)
H15A	0.5187	0.4973	0.7711	0.071*
H15B	0.4599	0.4907	0.6969	0.071*
C16	0.47477 (6)	0.41040 (2)	0.74405 (3)	0.04751 (19)
C17	0.46887 (6)	0.38192 (3)	0.80294 (3)	0.0512 (2)
C18	0.45183 (7)	0.41443 (3)	0.85971 (3)	0.0692 (2)
H18	0.4488	0.4559	0.8584	0.083*
C19	0.43994 (9)	0.38580 (3)	0.91545 (3)	0.0893 (3)
H19	0.4264	0.4079	0.9517	0.107*
C20	0.44760 (9)	0.32369 (3)	0.91951 (3)	0.0950 (3)
H20	0.4402	0.3048	0.9584	0.114*
C21	0.46566 (8)	0.29078 (3)	0.86726 (3)	0.0763 (3)
H21	0.4717	0.2494	0.8709	0.092*
C22	0.47565 (6)	0.31802 (3)	0.80672 (3)	0.0533 (2)
C23	0.48902 (6)	0.28476 (2)	0.75121 (3)	0.05025 (19)
C24	0.50832 (6)	0.31296 (2)	0.69371 (3)	0.04952 (19)
C25	0.53633 (7)	0.28147 (3)	0.63734 (3)	0.0717 (2)
H25	0.5385	0.2399	0.6381	0.086*
C26	0.55955 (9)	0.30999 (3)	0.58355 (3)	0.0917 (3)
H26	0.5783	0.2881	0.5478	0.110*
C27	0.55590 (9)	0.37184 (3)	0.58048 (3)	0.0920 (3)
H27	0.5754	0.3909	0.5431	0.110*
C28	0.52456 (7)	0.40490 (3)	0.63078 (3)	0.0694 (2)
H28	0.5181	0.4462	0.6269	0.083*
C29	0.50126 (6)	0.37734 (2)	0.68980 (3)	0.04805 (19)
C30	0.47742 (6)	0.21771 (3)	0.75480 (3)	0.0701 (2)
H30A	0.5021	0.2001	0.7153	0.084*
H30B	0.5523	0.2029	0.7903	0.084*
P1	0.26736 (2)	0.603967 (8)	0.597190 (8)	0.07065 (7)
P2	0.28659 (2)	0.408383 (8)	0.102339 (9)	0.06710 (6)
F1	0.36670 (15)	0.55203 (5)	0.57483 (6)	0.1373 (5)	0.3571 (3)
F2	0.41510 (12)	0.64165 (5)	0.58128 (5)	0.1000 (4)	0.3571 (3)
F3	0.19544 (18)	0.66224 (5)	0.61787 (8)	0.1638 (6)	0.3571 (3)
F4	0.14031 (12)	0.56558 (6)	0.62125 (6)	0.1136 (5)	0.3571 (3)
F5	0.18262 (15)	0.61130 (6)	0.52661 (5)	0.1226 (5)	0.3571 (3)
F6	0.37645 (13)	0.59947 (5)	0.66615 (4)	0.0918 (4)	0.3571 (3)
F1'	0.41611 (9)	0.56856 (4)	0.59362 (5)	0.1662 (4)	0.6429 (3)
F2'	0.33500 (9)	0.66460 (3)	0.57934 (4)	0.1252 (3)	0.6429 (3)
F3'	0.10150 (8)	0.63530 (3)	0.59970 (4)	0.1219 (3)	0.6429 (3)
F4'	0.19023 (8)	0.54187 (3)	0.61196 (3)	0.1047 (3)	0.6429 (3)
F5'	0.20880 (8)	0.59029 (3)	0.52393 (3)	0.1044 (3)	0.6429 (3)
F6'	0.30777 (9)	0.61625 (3)	0.67084 (3)	0.1264 (3)	0.6429 (3)
F7	0.24020 (9)	0.46823 (3)	0.13356 (4)	0.1555 (3)	0.6578 (4)
F8	0.15471 (7)	0.37902 (3)	0.13402 (3)	0.1253 (3)	0.6578 (4)
F9	0.34400 (9)	0.34987 (3)	0.07576 (4)	0.1332 (3)	0.6578 (4)
F10	0.41276 (7)	0.44284 (3)	0.07083 (3)	0.1174 (3)	0.6578 (4)
F11	0.16952 (8)	0.41836 (4)	0.04036 (4)	0.1414 (3)	0.6578 (4)
F12	0.41625 (7)	0.39921 (3)	0.16446 (3)	0.1084 (3)	0.6578 (4)
F7'	0.16290 (13)	0.46003 (5)	0.10290 (6)	0.1277 (5)	0.3422 (4)
F8'	0.19632 (13)	0.35501 (5)	0.13179 (6)	0.1141 (5)	0.3422 (4)
F9'	0.41047 (15)	0.36154 (7)	0.09097 (9)	0.1694 (7)	0.3422 (4)
F10'	0.39003 (15)	0.45706 (5)	0.07740 (7)	0.1274 (5)	0.3422 (4)
F11'	0.19825 (15)	0.38928 (5)	0.03506 (5)	0.1146 (5)	0.3422 (4)
F12'	0.35463 (16)	0.42317 (6)	0.17236 (5)	0.1244 (5)	0.3422 (4)
N5	0.10404 (8)	0.33843 (3)	0.62968 (3)	0.1066 (3)
C33	0.78555 (9)	0.53968 (3)	0.57477 (4)	0.1062 (3)
N7	0.78125 (10)	0.34258 (3)	0.09987 (5)	0.1602 (4)
N6	0.77573 (10)	0.52640 (3)	0.62429 (4)	0.1475 (4)
C31	0.08016 (10)	0.30883 (3)	0.58791 (4)	0.0984 (3)
C35	0.78060 (9)	0.38313 (4)	0.06853 (4)	0.1085 (4)
C36	0.78050 (10)	0.43712 (4)	0.03178 (4)	0.1259 (4)
H36A	0.7047	0.4643	0.0444	0.189*
H36B	0.7544	0.4281	−0.0133	0.189*
H36C	0.8824	0.4551	0.0396	0.189*
C32	0.04586 (14)	0.26820 (4)	0.53403 (4)	0.1746 (6)
H32A	0.0538	0.2278	0.5494	0.262*
H32B	0.1193	0.2744	0.5045	0.262*
H32C	−0.0583	0.2754	0.5124	0.262*
C34	0.80130 (13)	0.55765 (4)	0.51028 (5)	0.1661 (5)
H34A	0.7895	0.6002	0.5064	0.249*
H34B	0.7221	0.5384	0.4803	0.249*
H34C	0.9028	0.5463	0.5010	0.249*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0556 (3)	0.0417 (3)	0.0777 (3)	−0.0008 (2)	0.0171 (3)	0.0019 (3)
N2	0.0479 (3)	0.0565 (3)	0.0772 (3)	−0.0098 (2)	0.0135 (2)	−0.0031 (3)
N3	0.0414 (3)	0.0638 (3)	0.0782 (3)	0.0146 (2)	0.0086 (3)	0.0082 (3)
N4	0.0491 (3)	0.0423 (2)	0.0687 (3)	0.0038 (2)	0.0153 (2)	−0.0008 (2)
C1	0.0528 (3)	0.0522 (3)	0.0745 (4)	−0.0073 (3)	0.0095 (3)	0.0073 (3)
C2	0.0769 (4)	0.0443 (3)	0.0969 (5)	−0.0011 (3)	0.0216 (4)	0.0102 (3)
C3	0.0755 (4)	0.0515 (4)	0.0866 (4)	−0.0107 (3)	0.0235 (4)	0.0034 (3)
C4	0.0460 (4)	0.0814 (4)	0.0940 (5)	−0.0098 (4)	0.0084 (3)	0.0011 (4)
C5	0.0417 (3)	0.0684 (4)	0.0751 (4)	−0.0028 (3)	0.0135 (3)	0.0016 (3)
C6	0.1181 (6)	0.0812 (5)	0.0816 (5)	0.0093 (5)	0.0322 (4)	0.0146 (4)
C7	0.1896 (8)	0.0949 (6)	0.0756 (5)	0.0273 (6)	0.0475 (5)	0.0120 (4)
C8	0.1191 (6)	0.0819 (5)	0.0924 (5)	0.0216 (4)	0.0347 (4)	−0.0063 (4)
C9	0.0422 (3)	0.0669 (4)	0.0846 (4)	0.0098 (3)	0.0161 (3)	0.0089 (4)
C10	0.0315 (3)	0.0851 (4)	0.0627 (4)	0.0004 (3)	0.0044 (3)	0.0064 (3)
C11	0.0444 (4)	0.0794 (4)	0.1099 (5)	0.0140 (4)	0.0063 (4)	0.0117 (4)
C12	0.0704 (4)	0.0541 (4)	0.0833 (4)	0.0172 (3)	0.0211 (3)	−0.0024 (3)
C13	0.0693 (4)	0.0480 (3)	0.0787 (4)	0.0038 (3)	0.0196 (3)	−0.0075 (3)
C14	0.0529 (3)	0.0549 (3)	0.0670 (4)	0.0051 (3)	0.0077 (3)	−0.0025 (3)
C15	0.0500 (3)	0.0482 (3)	0.0837 (4)	−0.0050 (3)	0.0223 (3)	−0.0031 (3)
C16	0.0357 (3)	0.0427 (3)	0.0652 (4)	−0.0045 (3)	0.0110 (3)	−0.0056 (3)
C17	0.0380 (3)	0.0541 (3)	0.0606 (4)	−0.0039 (3)	0.0040 (3)	−0.0033 (3)
C18	0.0731 (4)	0.0731 (4)	0.0601 (4)	0.0040 (4)	0.0053 (3)	−0.0093 (3)
C19	0.1019 (5)	0.1020 (5)	0.0634 (4)	0.0083 (5)	0.0104 (4)	−0.0075 (4)
C20	0.1089 (6)	0.1175 (6)	0.0581 (4)	0.0018 (5)	0.0105 (4)	0.0186 (4)
C21	0.0756 (4)	0.0808 (4)	0.0707 (4)	0.0004 (4)	0.0051 (4)	0.0163 (4)
C22	0.0382 (3)	0.0573 (3)	0.0629 (4)	−0.0006 (3)	0.0029 (3)	0.0058 (3)
C23	0.0343 (3)	0.0401 (3)	0.0772 (4)	−0.0001 (3)	0.0112 (3)	−0.0025 (3)
C24	0.0304 (3)	0.0534 (3)	0.0657 (4)	−0.0022 (3)	0.0102 (3)	−0.0081 (3)
C25	0.0683 (4)	0.0658 (4)	0.0848 (4)	−0.0031 (4)	0.0238 (3)	−0.0190 (4)
C26	0.1060 (5)	0.1008 (5)	0.0757 (4)	−0.0030 (5)	0.0377 (4)	−0.0251 (4)
C27	0.1132 (5)	0.0969 (5)	0.0768 (4)	−0.0098 (5)	0.0502 (4)	−0.0042 (4)
C28	0.0728 (4)	0.0708 (4)	0.0702 (4)	−0.0057 (4)	0.0288 (3)	0.0047 (3)
C29	0.0343 (3)	0.0498 (3)	0.0616 (4)	−0.0044 (3)	0.0121 (3)	−0.0030 (3)
C30	0.0490 (4)	0.0579 (4)	0.1068 (5)	0.0026 (3)	0.0227 (3)	0.0056 (4)
P1	0.08036 (12)	0.07039 (11)	0.06361 (11)	−0.00682 (10)	0.01862 (9)	−0.00671 (10)
P2	0.06623 (11)	0.06613 (10)	0.07064 (11)	0.00215 (9)	0.01573 (9)	−0.00472 (9)
F1	0.1329 (9)	0.1137 (8)	0.1595 (10)	0.0288 (8)	0.0026 (8)	−0.0571 (7)
F2	0.1093 (8)	0.1029 (8)	0.0858 (7)	−0.0242 (7)	0.0079 (6)	0.0066 (6)
F3	0.1785 (11)	0.1382 (10)	0.1804 (11)	0.0607 (8)	0.0457 (9)	−0.0407 (8)
F4	0.0841 (7)	0.1513 (10)	0.1084 (8)	−0.0201 (7)	0.0239 (6)	0.0124 (7)
F5	0.1133 (9)	0.1353 (9)	0.1094 (9)	0.0328 (8)	−0.0160 (7)	0.0230 (8)
F6	0.1081 (8)	0.0953 (7)	0.0658 (6)	−0.0336 (6)	−0.0071 (6)	0.0139 (6)
F1'	0.1044 (5)	0.1873 (7)	0.2023 (8)	0.0454 (5)	0.0079 (5)	−0.0321 (6)
F2'	0.1505 (6)	0.0917 (4)	0.1325 (6)	−0.0474 (4)	0.0178 (5)	0.0162 (4)
F3'	0.1059 (5)	0.1250 (5)	0.1415 (5)	0.0122 (4)	0.0406 (4)	−0.0265 (5)
F4'	0.1352 (5)	0.0830 (4)	0.0960 (4)	−0.0338 (4)	0.0173 (4)	−0.0056 (4)
F5'	0.1297 (5)	0.1224 (5)	0.0631 (4)	−0.0221 (4)	0.0214 (4)	−0.0152 (4)
F6'	0.1702 (6)	0.1300 (5)	0.0786 (4)	−0.0496 (5)	0.0174 (4)	−0.0264 (4)
F7	0.1567 (6)	0.1295 (5)	0.1872 (6)	0.0447 (5)	0.0487 (5)	−0.0561 (5)
F8	0.0947 (4)	0.1414 (5)	0.1469 (5)	−0.0237 (4)	0.0414 (4)	0.0158 (5)
F9	0.1209 (5)	0.0892 (4)	0.1847 (6)	0.0133 (4)	0.0071 (5)	−0.0620 (4)
F10	0.1181 (4)	0.1182 (5)	0.1313 (5)	−0.0193 (4)	0.0692 (3)	0.0004 (4)
F11	0.1152 (5)	0.1628 (6)	0.1288 (6)	0.0188 (5)	−0.0395 (5)	0.0289 (5)
F12	0.0968 (4)	0.1279 (5)	0.0901 (4)	−0.0080 (4)	−0.0205 (4)	0.0135 (4)
F7'	0.1152 (8)	0.1255 (9)	0.1485 (10)	0.0598 (7)	0.0392 (7)	−0.0089 (8)
F8'	0.1357 (9)	0.1077 (8)	0.0974 (8)	−0.0560 (7)	0.0120 (7)	0.0295 (6)
F9'	0.1324 (11)	0.1465 (11)	0.2222 (14)	0.0606 (9)	0.0022 (10)	−0.0072 (10)
F10'	0.1476 (10)	0.0793 (7)	0.1564 (11)	−0.0420 (7)	0.0258 (8)	0.0192 (7)
F11'	0.1341 (10)	0.1309 (9)	0.0779 (7)	−0.0209 (8)	0.0128 (7)	−0.0379 (7)
F12'	0.1456 (10)	0.1269 (9)	0.0901 (8)	−0.0403 (8)	−0.0183 (8)	−0.0187 (7)
N5	0.1129 (5)	0.1193 (5)	0.0862 (4)	−0.0112 (4)	0.0107 (4)	−0.0123 (4)
C33	0.0956 (5)	0.0604 (4)	0.1496 (7)	−0.0105 (4)	−0.0249 (5)	0.0102 (5)
N7	0.1228 (6)	0.1230 (6)	0.2330 (10)	−0.0107 (5)	0.0204 (6)	0.0198 (6)
N6	0.1724 (7)	0.1040 (5)	0.1587 (7)	−0.0232 (5)	−0.0005 (6)	0.0303 (5)
C31	0.1251 (6)	0.0961 (5)	0.0697 (5)	0.0003 (5)	−0.0004 (5)	0.0068 (4)
C35	0.0741 (5)	0.1131 (6)	0.1368 (7)	−0.0023 (5)	0.0105 (5)	−0.0244 (6)
C36	0.1063 (6)	0.1524 (8)	0.1174 (7)	0.0097 (6)	0.0105 (6)	0.0157 (6)
C32	0.2809 (14)	0.1239 (8)	0.1016 (7)	−0.0034 (9)	−0.0294 (9)	−0.0183 (6)
C34	0.2075 (11)	0.1517 (8)	0.1201 (8)	−0.0390 (8)	−0.0378 (8)	0.0088 (7)

Geometric parameters (Å, º) top

N1—C1	1.3163 (7)	C23—C30	1.5073 (9)
N1—C2	1.3673 (8)	C24—C25	1.4281 (9)
N1—C30	1.4767 (8)	C24—C29	1.4446 (9)
N2—C1	1.3202 (8)	C25—C26	1.3377 (10)
N2—C3	1.3663 (8)	C25—H25	0.9300
N2—C4	1.4789 (8)	C26—C27	1.3865 (11)
N3—C14	1.3216 (8)	C26—H26	0.9300
N3—C12	1.3674 (8)	C27—C28	1.3490 (10)
N3—C11	1.4786 (8)	C27—H27	0.9300
N4—C14	1.3192 (7)	C28—C29	1.4244 (9)
N4—C13	1.3679 (8)	C28—H28	0.9300
N4—C15	1.4728 (8)	C30—H30A	0.9700
C1—H1	0.9300	C30—H30B	0.9700
C2—C3	1.3259 (10)	P1—F1'	1.5216 (9)
C2—H2	0.9300	P1—F3	1.5353 (14)
C3—H3	0.9300	P1—F4	1.5374 (12)
C4—C5	1.4997 (10)	P1—F2'	1.5459 (8)
C4—H4A	0.9700	P1—F6'	1.5577 (7)
C4—H4B	0.9700	P1—F1	1.5584 (12)
C5—C6	1.3669 (10)	P1—F5	1.5606 (11)
C5—C10	1.3836 (9)	P1—F5'	1.5756 (7)
C6—C7	1.3692 (11)	P1—F4'	1.5921 (7)
C6—H6	0.9300	P1—F3'	1.6038 (8)
C7—C8	1.3707 (11)	P1—F2	1.6062 (12)
C7—H7	0.9300	P1—F6	1.6090 (9)
C8—C9	1.3714 (10)	P2—F9	1.5347 (7)
C8—H8	0.9300	P2—F12'	1.5358 (12)
C9—C10	1.3768 (9)	P2—F11	1.5414 (8)
C9—C11	1.5025 (10)	P2—F9'	1.5423 (15)
C10—H10	0.9300	P2—F8	1.5483 (8)
C11—H11A	0.9700	P2—F10'	1.5489 (13)
C11—H11B	0.9700	P2—F10	1.5603 (7)
C12—C13	1.3385 (9)	P2—F11'	1.5621 (11)
C12—H12	0.9300	P2—F7	1.5694 (8)
C13—H13	0.9300	P2—F7'	1.5760 (12)
C14—H14	0.9300	P2—F8'	1.6004 (13)
C15—C16	1.5052 (8)	P2—F12	1.6016 (7)
C15—H15A	0.9700	N5—C31	1.0938 (10)
C15—H15B	0.9700	C33—N6	1.0960 (13)
C16—C17	1.3983 (8)	C33—C34	1.4374 (14)
C16—C29	1.4047 (8)	N7—C35	1.1206 (13)
C17—C18	1.4219 (9)	C31—C32	1.4472 (12)
C17—C22	1.4337 (9)	C35—C36	1.4337 (13)
C18—C19	1.3510 (10)	C36—H36A	0.9600
C18—H18	0.9300	C36—H36B	0.9600
C19—C20	1.3942 (11)	C36—H36C	0.9600
C19—H19	0.9300	C32—H32A	0.9600
C20—C21	1.3490 (10)	C32—H32B	0.9600
C20—H20	0.9300	C32—H32C	0.9600
C21—C22	1.4233 (9)	C34—H34A	0.9600
C21—H21	0.9300	C34—H34B	0.9600
C22—C23	1.4016 (9)	C34—H34C	0.9600
C23—C24	1.3934 (9)

C1—N1—C2	108.31 (5)	F1—P1—F5	89.71 (7)
C1—N1—C30	125.37 (5)	F1'—P1—F5'	90.15 (5)
C2—N1—C30	126.30 (5)	F3—P1—F5'	110.84 (6)
C1—N2—C3	108.16 (5)	F4—P1—F5'	94.00 (5)
C1—N2—C4	123.98 (5)	F2'—P1—F5'	90.73 (4)
C3—N2—C4	127.54 (5)	F6'—P1—F5'	174.13 (4)
C14—N3—C12	109.09 (5)	F1—P1—F5'	70.92 (5)
C14—N3—C11	123.81 (5)	F5—P1—F5'	19.40 (5)
C12—N3—C11	126.82 (5)	F1'—P1—F4'	86.32 (5)
C14—N4—C13	108.73 (5)	F3—P1—F4'	119.24 (7)
C14—N4—C15	125.25 (5)	F4—P1—F4'	26.85 (5)
C13—N4—C15	125.82 (5)	F2'—P1—F4'	176.68 (4)
N1—C1—N2	108.74 (5)	F6'—P1—F4'	89.99 (4)
N1—C1—H1	125.6	F1—P1—F4'	70.86 (6)
N2—C1—H1	125.6	F5—P1—F4'	97.20 (5)
C3—C2—N1	107.32 (5)	F5'—P1—F4'	86.38 (4)
C3—C2—H2	126.3	F1'—P1—F3'	174.44 (4)
N1—C2—H2	126.3	F3—P1—F3'	38.53 (6)
C2—C3—N2	107.46 (6)	F4—P1—F3'	63.16 (5)
C2—C3—H3	126.3	F2'—P1—F3'	89.75 (4)
N2—C3—H3	126.3	F6'—P1—F3'	87.74 (4)
N2—C4—C5	110.79 (5)	F1—P1—F3'	150.60 (5)
N2—C4—H4A	109.5	F5—P1—F3'	71.87 (6)
C5—C4—H4A	109.5	F5'—P1—F3'	87.55 (4)
N2—C4—H4B	109.5	F4'—P1—F3'	88.49 (4)
C5—C4—H4B	109.5	F1'—P1—F2	63.90 (6)
H4A—C4—H4B	108.1	F3—P1—F2	88.85 (7)
C6—C5—C10	118.51 (6)	F4—P1—F2	172.03 (6)
C6—C5—C4	120.41 (6)	F2'—P1—F2	31.53 (5)
C10—C5—C4	121.02 (6)	F6'—P1—F2	92.58 (5)
C5—C6—C7	120.09 (7)	F1—P1—F2	80.74 (6)
C5—C6—H6	120.0	F5—P1—F2	91.34 (6)
C7—C6—H6	120.0	F5'—P1—F2	92.85 (5)
C6—C7—C8	121.02 (7)	F4'—P1—F2	150.21 (5)
C6—C7—H7	119.5	F3'—P1—F2	121.26 (5)
C8—C7—H7	119.5	F1'—P1—F6	67.96 (5)
C7—C8—C9	120.05 (7)	F3—P1—F6	90.40 (7)
C7—C8—H8	120.0	F4—P1—F6	91.24 (6)
C9—C8—H8	120.0	F2'—P1—F6	94.62 (5)
C8—C9—C10	118.47 (6)	F6'—P1—F6	26.28 (5)
C8—C9—C11	121.33 (6)	F1—P1—F6	87.04 (6)
C10—C9—C11	120.19 (6)	F5—P1—F6	171.98 (6)
C9—C10—C5	121.85 (6)	F5'—P1—F6	157.83 (5)
C9—C10—H10	119.1	F4'—P1—F6	88.67 (4)
C5—C10—H10	119.1	F3'—P1—F6	113.93 (5)
N3—C11—C9	110.54 (5)	F2—P1—F6	80.90 (6)
N3—C11—H11A	109.5	F9—P2—F12'	115.66 (6)
C9—C11—H11A	109.5	F9—P2—F11	91.39 (4)
N3—C11—H11B	109.5	F12'—P2—F11	152.46 (6)
C9—C11—H11B	109.5	F9—P2—F9'	25.07 (6)
H11A—C11—H11B	108.1	F12'—P2—F9'	96.79 (8)
C13—C12—N3	106.68 (5)	F11—P2—F9'	110.62 (7)
C13—C12—H12	126.7	F9—P2—F8	95.26 (4)
N3—C12—H12	126.7	F12'—P2—F8	83.27 (6)
C12—C13—N4	107.33 (5)	F11—P2—F8	89.47 (4)
C12—C13—H13	126.3	F9'—P2—F8	110.46 (7)
N4—C13—H13	126.3	F9—P2—F10'	104.13 (6)
N4—C14—N3	108.17 (5)	F12'—P2—F10'	90.75 (7)
N4—C14—H14	125.9	F11—P2—F10'	87.28 (6)
N3—C14—H14	125.9	F9'—P2—F10'	88.72 (8)
N4—C15—C16	110.23 (4)	F8—P2—F10'	160.41 (6)
N4—C15—H15A	109.6	F9—P2—F10	89.10 (4)
C16—C15—H15A	109.6	F12'—P2—F10	96.09 (6)
N4—C15—H15B	109.6	F11—P2—F10	89.06 (4)
C16—C15—H15B	109.6	F9'—P2—F10	74.10 (7)
H15A—C15—H15B	108.1	F8—P2—F10	175.43 (4)
C17—C16—C29	120.49 (5)	F10'—P2—F10	15.10 (5)
C17—C16—C15	118.64 (5)	F9—P2—F11'	65.10 (5)
C29—C16—C15	120.82 (5)	F12'—P2—F11'	172.08 (7)
C16—C17—C18	121.91 (6)	F11—P2—F11'	26.50 (5)
C16—C17—C22	119.83 (5)	F9'—P2—F11'	86.08 (8)
C18—C17—C22	118.23 (5)	F8—P2—F11'	88.81 (6)
C19—C18—C17	120.85 (6)	F10'—P2—F11'	96.70 (7)
C19—C18—H18	119.6	F10—P2—F11'	91.79 (6)
C17—C18—H18	119.6	F9—P2—F7	175.40 (4)
C18—C19—C20	121.14 (7)	F12'—P2—F7	60.13 (6)
C18—C19—H19	119.4	F11—P2—F7	92.98 (4)
C20—C19—H19	119.4	F9'—P2—F7	150.60 (6)
C21—C20—C19	120.36 (7)	F8—P2—F7	86.19 (4)
C21—C20—H20	119.8	F10'—P2—F7	74.70 (6)
C19—C20—H20	119.8	F10—P2—F7	89.57 (4)
C20—C21—C22	121.39 (7)	F11'—P2—F7	119.35 (5)
C20—C21—H21	119.3	F9—P2—F7'	152.27 (5)
C22—C21—H21	119.3	F12'—P2—F7'	89.93 (7)
C23—C22—C21	122.51 (6)	F11—P2—F7'	62.53 (5)
C23—C22—C17	119.48 (5)	F9'—P2—F7'	170.85 (8)
C21—C22—C17	118.01 (6)	F8—P2—F7'	76.41 (6)
C24—C23—C22	120.92 (5)	F10'—P2—F7'	84.97 (7)
C24—C23—C30	120.80 (5)	F10—P2—F7'	99.08 (6)
C22—C23—C30	118.26 (5)	F11'—P2—F7'	88.07 (6)
C23—C24—C25	123.36 (6)	F7—P2—F7'	32.32 (5)
C23—C24—C29	119.47 (5)	F9—P2—F8'	72.85 (6)
C25—C24—C29	117.16 (5)	F12'—P2—F8'	86.05 (7)
C26—C25—C24	121.88 (6)	F11—P2—F8'	97.90 (5)
C26—C25—H25	119.1	F9'—P2—F8'	86.63 (8)
C24—C25—H25	119.1	F8—P2—F8'	23.84 (5)
C25—C26—C27	120.71 (7)	F10'—P2—F8'	174.00 (6)
C25—C26—H26	119.6	F10—P2—F8'	160.72 (5)
C27—C26—H26	119.6	F11'—P2—F8'	86.76 (6)
C28—C27—C26	121.18 (7)	F7—P2—F8'	107.89 (6)
C28—C27—H27	119.4	F7'—P2—F8'	100.08 (7)
C26—C27—H27	119.4	F9—P2—F12	87.79 (4)
C27—C28—C29	120.86 (6)	F12'—P2—F12	29.09 (6)
C27—C28—H28	119.6	F11—P2—F12	176.65 (4)
C29—C28—H28	119.6	F9'—P2—F12	67.70 (7)
C16—C29—C28	122.48 (5)	F8—P2—F12	93.85 (4)
C16—C29—C24	119.37 (5)	F10'—P2—F12	89.76 (6)
C28—C29—C24	118.14 (5)	F10—P2—F12	87.68 (4)
N1—C30—C23	109.96 (5)	F11'—P2—F12	152.88 (5)
N1—C30—H30A	109.7	F7—P2—F12	87.76 (4)
C23—C30—H30A	109.7	F7'—P2—F12	118.80 (5)
N1—C30—H30B	109.7	F8'—P2—F12	84.97 (5)
C23—C30—H30B	109.7	N6—C33—C34	178.88 (10)
H30A—C30—H30B	108.2	N5—C31—C32	177.95 (10)
F1'—P1—F3	146.83 (7)	N7—C35—C36	176.64 (10)
F1'—P1—F4	112.00 (6)	C35—C36—H36A	109.5
F3—P1—F4	92.50 (8)	C35—C36—H36B	109.5
F1'—P1—F2'	95.34 (5)	H36A—C36—H36B	109.5
F3—P1—F2'	60.36 (7)	C35—C36—H36C	109.5
F4—P1—F2'	152.20 (6)	H36A—C36—H36C	109.5
F1'—P1—F6'	94.23 (5)	H36B—C36—H36C	109.5
F3—P1—F6'	67.06 (7)	C31—C32—H32A	109.5
F4—P1—F6'	80.74 (5)	C31—C32—H32B	109.5
F2'—P1—F6'	92.75 (4)	H32A—C32—H32B	109.5
F1'—P1—F1	24.40 (5)	C31—C32—H32C	109.5
F3—P1—F1	169.54 (8)	H32A—C32—H32C	109.5
F4—P1—F1	97.69 (7)	H32B—C32—H32C	109.5
F2'—P1—F1	109.72 (6)	C33—C34—H34A	109.5
F6'—P1—F1	112.20 (5)	C33—C34—H34B	109.5
F1'—P1—F5	106.83 (6)	H34A—C34—H34B	109.5
F3—P1—F5	91.49 (8)	C33—C34—H34C	109.5
F4—P1—F5	96.47 (7)	H34A—C34—H34C	109.5
F2'—P1—F5	79.57 (6)	H34B—C34—H34C	109.5
F6'—P1—F5	158.09 (6)

C2—N1—C1—N2	0.95 (7)	C15—C16—C17—C18	−6.67 (8)
C30—N1—C1—N2	−177.53 (5)	C29—C16—C17—C22	−5.69 (8)
C3—N2—C1—N1	−0.70 (7)	C15—C16—C17—C22	171.55 (5)
C4—N2—C1—N1	173.20 (5)	C16—C17—C18—C19	177.25 (6)
C1—N1—C2—C3	−0.84 (7)	C22—C17—C18—C19	−1.00 (9)
C30—N1—C2—C3	177.63 (6)	C17—C18—C19—C20	1.50 (10)
N1—C2—C3—N2	0.40 (7)	C18—C19—C20—C21	−0.65 (11)
C1—N2—C3—C2	0.17 (7)	C19—C20—C21—C22	−0.69 (11)
C4—N2—C3—C2	−173.46 (6)	C20—C21—C22—C23	−177.76 (6)
C1—N2—C4—C5	−60.35 (8)	C20—C21—C22—C17	1.13 (9)
C3—N2—C4—C5	112.35 (7)	C16—C17—C22—C23	0.35 (8)
N2—C4—C5—C6	−72.17 (8)	C18—C17—C22—C23	178.63 (5)
N2—C4—C5—C10	105.10 (6)	C16—C17—C22—C21	−178.58 (5)
C10—C5—C6—C7	−0.79 (10)	C18—C17—C22—C21	−0.29 (8)
C4—C5—C6—C7	176.55 (7)	C21—C22—C23—C24	−175.97 (5)
C5—C6—C7—C8	0.44 (13)	C17—C22—C23—C24	5.15 (8)
C6—C7—C8—C9	−0.18 (13)	C21—C22—C23—C30	5.72 (8)
C7—C8—C9—C10	0.29 (11)	C17—C22—C23—C30	−173.15 (5)
C7—C8—C9—C11	−178.19 (7)	C22—C23—C24—C25	174.29 (5)
C8—C9—C10—C5	−0.67 (9)	C30—C23—C24—C25	−7.45 (8)
C11—C9—C10—C5	177.82 (5)	C22—C23—C24—C29	−5.25 (7)
C6—C5—C10—C9	0.92 (9)	C30—C23—C24—C29	173.01 (5)
C4—C5—C10—C9	−176.41 (5)	C23—C24—C25—C26	−177.72 (6)
C14—N3—C11—C9	64.07 (8)	C29—C24—C25—C26	1.83 (8)
C12—N3—C11—C9	−109.08 (7)	C24—C25—C26—C27	−0.53 (10)
C8—C9—C11—N3	73.67 (8)	C25—C26—C27—C28	−1.90 (11)
C10—C9—C11—N3	−104.78 (6)	C26—C27—C28—C29	2.91 (10)
C14—N3—C12—C13	−0.28 (7)	C17—C16—C29—C28	−173.25 (5)
C11—N3—C12—C13	173.71 (6)	C15—C16—C29—C28	9.57 (8)
N3—C12—C13—N4	0.22 (7)	C17—C16—C29—C24	5.57 (7)
C14—N4—C13—C12	−0.09 (7)	C15—C16—C29—C24	−171.61 (5)
C15—N4—C13—C12	−175.20 (5)	C27—C28—C29—C16	177.34 (6)
C13—N4—C14—N3	−0.08 (6)	C27—C28—C29—C24	−1.50 (8)
C15—N4—C14—N3	175.06 (5)	C23—C24—C29—C16	−0.11 (7)
C12—N3—C14—N4	0.22 (7)	C25—C24—C29—C16	−179.68 (5)
C11—N3—C14—N4	−173.99 (5)	C23—C24—C29—C28	178.76 (5)
C14—N4—C15—C16	−34.62 (7)	C25—C24—C29—C28	−0.81 (7)
C13—N4—C15—C16	139.70 (5)	C1—N1—C30—C23	29.28 (8)
N4—C15—C16—C17	−63.26 (6)	C2—N1—C30—C23	−148.93 (6)
N4—C15—C16—C29	113.98 (6)	C24—C23—C30—N1	−111.55 (6)
C29—C16—C17—C18	176.09 (5)	C22—C23—C30—N1	66.75 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N5	0.93	2.52	3.407 (3)	160
C14—H14···N5	0.93	2.47	3.387 (3)	167

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