[(Z)-3-Di­methyl­amino-2-(1,3-dioxo-2,3-di­hydro-1H-isoindol-2-yl)­allyl­idene]­di­methyl­ammonium hexa­fluoro­phosphate

At 150 K, the asymmetric unit of the crystal structure of the title compound, C₁₅H₁₈N₃O₂⁺·PF₆^-, comprises two mol­ecules. The geometric parameters for the two cations are similar, with the most significant difference being the magnitude of the dihedral angle between the two planar regions of each mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.045
• wR factor = 0.118
• Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....         P2
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....         P1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      30.00 Perc.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              F6 P
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              F6 P

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

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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: X-STEP32 (Stoe & Cie, 2001) and WinGX (Farrugia, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX.

[(Z)-3-Dimethylamino-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)- allylidene]dimethylammonium hexafluorophosphate

Crystal data

C15H18N3O2^+·F6P^−	Z = 4
Mr = 417.29	F(000) = 856
Triclinic, P1	Dx = 1.489 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2929 (9) Å	Cell parameters from 19784 reflections
b = 10.8379 (11) Å	θ = 1.9–29.7°
c = 18.7453 (19) Å	µ = 0.22 mm^−1
α = 85.696 (8)°	T = 150 K
β = 84.306 (8)°	Lath, yellow
γ = 83.175 (8)°	0.60 × 0.25 × 0.10 mm
V = 1861.5 (3) Å^3

Data collection

Stoe IPDS-II area-detector diffractometer	5375 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
Graphite monochromator	θmax = 29.7°, θmin = 1.9°
φ and ω scans	h = −11→12
41451 measured reflections	k = −15→15
10507 independent reflections	l = −26→26

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0669P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.81	(Δ/σ)max = 0.009
10507 reflections	Δρmax = 0.52 e Å^−3
521 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (7)

Special details

Experimental. The crystal was mounted under the perfluoro-polyether PFO-XR75 (Lancaster Synthesis). A total of 350 frames (3 minute exposure) were collected (phi/omega: 45/10–170, 105/160–180, 155/10–180, delta-omega = 1 °.)

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.

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d

Plane 1 m1 = 0.10686(0.00057) m2 = -0.11509(0.00069) m3 = -0.98759(0.00001) D = -11.27837(0.00259) Atom d s d/s (d/s)**2 C1 * -0.0547 0.0017 - 32.600 1062.783 C2 * -0.0351 0.0019 - 18.832 354.662 C3 * -0.0478 0.0017 - 28.464 810.190 N2 * 0.0220 0.0017 13.171 173.480 N3 * -0.0280 0.0015 - 18.779 352.638 C4 * 0.0687 0.0022 30.827 950.303 C5 * 0.0192 0.0022 8.628 74.451 C6 * 0.0378 0.0022 16.943 287.059 C7 * 0.1085 0.0020 53.029 2812.127 N1 - 0.0231 0.0013 - 17.668 312.167 ============ Sum((d/s)**2) for starred atoms 6877.692 Chi-squared at 95% for 6 degrees of freedom: 12.60 The group of atoms deviates significantly from planarity

Plane 2 m1 = -0.71256(0.00023) m2 = 0.69600(0.00024) m3 = -0.08860(0.00037) D = -2.91254(0.00479) Atom d s d/s (d/s)**2 N1 * -0.0208 0.0015 - 14.251 203.087 O1 * -0.0062 0.0015 - 4.120 16.976 O2 * -0.0164 0.0015 - 11.203 125.513 C8 * 0.0142 0.0018 7.826 61.251 C9 * 0.0041 0.0018 2.335 5.452 C10 * 0.0357 0.0018 19.726 389.129 C11 * 0.0389 0.0017 22.732 516.740 C12 * 0.0290 0.0019 15.132 228.968 C13 * -0.0293 0.0020 - 14.494 210.070 C14 * -0.0465 0.0021 - 22.500 506.244 C15 * 0.0022 0.0020 1.099 1.207 C1 - 0.1681 0.0018 - 95.422 9105.425 ============ Sum((d/s)**2) for starred atoms 2264.638 Chi-squared at 95% for 8 degrees of freedom: 15.50 The group of atoms deviates significantly from planarity

Plane 3 m1 = -0.17367(0.00056) m2 = 0.14887(0.00071) m3 = -0.97349(0.00004) D = -17.20303(0.00592) Atom d s d/s (d/s)**2 C21 * 0.0385 0.0019 20.696 428.320 C22 * 0.0594 0.0017 35.265 1243.617 C23 * 0.0318 0.0019 17.063 291.149 N22 * 0.0207 0.0015 13.875 192.514 N23 * -0.0038 0.0017 - 2.247 5.048 C24 * -0.0804 0.0020 - 39.320 1546.098 C25 * -0.0529 0.0020 - 25.813 666.293 C26 * 0.0035 0.0022 1.590 2.529 C27 * -0.0895 0.0022 - 40.155 1612.415 N21 - 0.0361 0.0015 - 24.269 588.976 ============ Sum((d/s)**2) for starred atoms 5987.982 Chi-squared at 95% for 6 degrees of freedom: 12.60 The group of atoms deviates significantly from planarity

Plane 4 m1 = 0.70595(0.00023) m2 = -0.69921(0.00023) m3 = -0.11282(0.00040) D = 3.31507(0.00765) Atom d s d/s (d/s)**2 N21 * 0.0296 0.0015 20.276 411.100 O21 * -0.0056 0.0016 - 3.627 13.152 O22 * 0.0139 0.0016 8.922 79.593 C28 * -0.0090 0.0019 - 4.699 22.076 C29 * -0.0061 0.0018 - 3.391 11.499 C30 * -0.0326 0.0018 - 18.016 324.573 C31 * -0.0400 0.0018 - 22.088 487.865 C32 * -0.0339 0.0020 - 16.797 282.133 C33 * 0.0226 0.0021 10.643 113.265 C34 * 0.0495 0.0021 23.909 571.623 C35 * 0.0042 0.0021 2.021 4.083 C21 0.1890 0.0018 104.366 10892.305 ============ Sum((d/s)**2) for starred atoms 2320.963 Chi-squared at 95% for 8 degrees of freedom: 15.50 The group of atoms deviates significantly from planarity

Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 86.06 (0.04) 93.94 (0.04) 1 3 22.22 (0.05) 157.78 (0.05) 1 4 74.49 (0.04) 105.51 (0.04) 2 3 71.72 (0.04) 108.28 (0.04) 2 4 11.57 (0.03) 168.43 (0.03) 3 4 83.29 (0.04) 96.71 (0.04)

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.02863 (6)	−0.32919 (5)	0.62382 (3)	0.03771 (13)
P2	0.55338 (6)	−0.30975 (5)	0.86929 (3)	0.04090 (14)
F1	0.11202 (17)	−0.23924 (12)	0.56673 (7)	0.0637 (4)
F2	−0.05027 (16)	−0.41764 (14)	0.68184 (8)	0.0704 (4)
F3	−0.02652 (15)	−0.21139 (12)	0.67031 (7)	0.0567 (3)
F4	0.0857 (2)	−0.44220 (13)	0.57644 (9)	0.0812 (5)
F5	0.17019 (14)	−0.35167 (13)	0.66725 (8)	0.0627 (4)
F6	−0.11372 (17)	−0.30374 (16)	0.58271 (8)	0.0746 (4)
F7	0.4841 (2)	−0.40337 (15)	0.92703 (8)	0.0678 (6)	0.883 (2)
F8	0.6205 (2)	−0.21030 (17)	0.81126 (8)	0.0643 (6)	0.883 (2)
F9	0.6907 (2)	−0.3135 (2)	0.91138 (10)	0.0949 (8)	0.883 (2)
F10	0.41110 (18)	−0.29302 (17)	0.82617 (10)	0.0697 (5)	0.883 (2)
F11	0.4816 (3)	−0.19430 (16)	0.91573 (9)	0.0809 (7)	0.883 (2)
F12	0.6161 (3)	−0.41872 (16)	0.82117 (9)	0.0747 (6)	0.883 (2)
F13	0.6970 (15)	−0.2975 (14)	0.8212 (8)	0.072 (2)	0.117 (2)
F14	0.5953 (19)	−0.2249 (15)	0.9275 (8)	0.072 (2)	0.117 (2)
F15	0.3981 (15)	−0.3115 (14)	0.9100 (8)	0.072 (2)	0.117 (2)
F16	0.4797 (15)	−0.2136 (13)	0.8263 (7)	0.072 (2)	0.117 (2)
F17	0.5106 (17)	−0.4097 (14)	0.8184 (8)	0.072 (2)	0.117 (2)
F18	0.6284 (15)	−0.4204 (13)	0.9204 (7)	0.072 (2)	0.117 (2)
O1	0.36175 (17)	0.16513 (13)	0.75049 (7)	0.0458 (4)
O2	0.43115 (16)	0.15373 (13)	0.50586 (7)	0.0426 (3)
O21	0.91901 (17)	0.22554 (14)	0.75680 (7)	0.0469 (4)
O22	0.90471 (17)	0.14864 (14)	1.00052 (7)	0.0458 (4)
N1	0.37381 (16)	0.13542 (13)	0.62894 (7)	0.0280 (3)
N2	0.05031 (17)	0.14062 (14)	0.60863 (9)	0.0344 (3)
N3	0.48987 (16)	−0.13779 (13)	0.65191 (8)	0.0311 (3)
N21	0.89092 (16)	0.16279 (13)	0.87734 (8)	0.0295 (3)
N22	1.01595 (17)	−0.10013 (14)	0.84334 (8)	0.0324 (3)
N23	0.56205 (17)	0.16009 (14)	0.90442 (9)	0.0356 (4)
C1	0.29218 (19)	0.03191 (16)	0.63246 (9)	0.0302 (4)
C2	0.1440 (2)	0.04330 (16)	0.62267 (10)	0.0325 (4)
H2A	0.1034	−0.0336	0.6270	0.039*
C3	0.3563 (2)	−0.09144 (16)	0.64297 (9)	0.0305 (4)
H3A	0.2903	−0.1522	0.6437	0.037*
C4	0.0828 (2)	0.27051 (17)	0.60004 (12)	0.0408 (5)
H4A	0.1323	0.2893	0.6411	0.049*
H4B	−0.0081	0.3260	0.5977	0.049*
H4C	0.1459	0.2829	0.5556	0.049*
C5	−0.1011 (2)	0.12211 (19)	0.60169 (12)	0.0420 (5)
H5A	−0.1120	0.0330	0.6079	0.050*
H5B	−0.1277	0.1546	0.5540	0.050*
H5C	−0.1649	0.1663	0.6386	0.050*
C6	0.6134 (2)	−0.06574 (18)	0.65069 (12)	0.0394 (4)
H6A	0.6256	−0.0186	0.6042	0.047*
H6B	0.7019	−0.1223	0.6579	0.047*
H6C	0.5957	−0.0079	0.6892	0.047*
C7	0.5281 (2)	−0.27324 (16)	0.65467 (11)	0.0379 (4)
H7C	0.5839	−0.2992	0.6960	0.046*
H7B	0.5868	−0.2965	0.6104	0.046*
H7A	0.4390	−0.3145	0.6595	0.046*
C8	0.4058 (2)	0.19272 (16)	0.68942 (10)	0.0317 (4)
C9	0.44210 (19)	0.18707 (16)	0.56471 (9)	0.0297 (4)
C10	0.5049 (2)	0.28661 (16)	0.66130 (10)	0.0325 (4)
C11	0.52571 (19)	0.28390 (15)	0.58705 (10)	0.0307 (4)
C12	0.6159 (2)	0.35992 (17)	0.54621 (12)	0.0389 (4)
H12	0.6276	0.3599	0.4953	0.047*
C13	0.6890 (2)	0.43679 (18)	0.58316 (13)	0.0453 (5)
H13	0.7536	0.4890	0.5570	0.054*
C14	0.6690 (2)	0.43817 (18)	0.65735 (13)	0.0465 (5)
H14	0.7208	0.4910	0.6810	0.056*
C15	0.5755 (2)	0.36457 (17)	0.69784 (12)	0.0411 (5)
H15	0.5602	0.3673	0.7486	0.049*
C21	0.8105 (2)	0.06011 (16)	0.87261 (10)	0.0314 (4)
C22	0.8789 (2)	−0.05845 (16)	0.85648 (9)	0.0321 (4)
H22A	0.8137	−0.1192	0.8548	0.038*
C23	0.6590 (2)	0.06733 (17)	0.88691 (10)	0.0340 (4)
H23A	0.6198	−0.0088	0.8832	0.041*
C24	1.1395 (2)	−0.02788 (18)	0.84341 (11)	0.0400 (4)
H24A	1.1342	0.0113	0.8892	0.048*
H24B	1.1364	0.0366	0.8039	0.048*
H24C	1.2306	−0.0833	0.8372	0.048*
C25	1.0564 (2)	−0.23398 (17)	0.83370 (11)	0.0406 (4)
H25A	0.9681	−0.2748	0.8325	0.049*
H25B	1.1102	−0.2716	0.8738	0.049*
H25C	1.1176	−0.2445	0.7884	0.049*
C26	0.5922 (2)	0.28817 (18)	0.91102 (12)	0.0441 (5)
H26A	0.6597	0.3131	0.8704	0.053*
H26B	0.6360	0.2931	0.9560	0.053*
H26C	0.5012	0.3440	0.9110	0.053*
C27	0.4092 (2)	0.1382 (2)	0.92096 (12)	0.0444 (5)
H27A	0.4002	0.0496	0.9179	0.053*
H27B	0.3499	0.1876	0.8864	0.053*
H27C	0.3756	0.1627	0.9696	0.053*
C28	0.9440 (2)	0.23587 (17)	0.81775 (10)	0.0335 (4)
C29	0.9359 (2)	0.19695 (16)	0.94192 (10)	0.0322 (4)
C30	1.0339 (2)	0.32159 (16)	0.84655 (10)	0.0337 (4)
C31	1.0282 (2)	0.29879 (16)	0.92090 (10)	0.0328 (4)
C32	1.1042 (2)	0.36292 (18)	0.96283 (12)	0.0409 (5)
H32	1.0977	0.3490	1.0136	0.049*
C33	1.1907 (2)	0.44890 (19)	0.92732 (14)	0.0485 (5)
H33	1.2457	0.4937	0.9544	0.058*
C34	1.1984 (2)	0.47062 (18)	0.85348 (14)	0.0492 (6)
H34	1.2596	0.5292	0.8309	0.059*
C35	1.1183 (2)	0.40824 (18)	0.81152 (12)	0.0430 (5)
H35	1.1215	0.4247	0.7609	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0381 (3)	0.0339 (3)	0.0432 (3)	−0.0119 (2)	−0.0048 (2)	−0.0023 (2)
P2	0.0462 (3)	0.0445 (3)	0.0361 (3)	−0.0206 (2)	−0.0041 (2)	−0.0047 (2)
F1	0.0887 (11)	0.0554 (8)	0.0487 (7)	−0.0303 (8)	0.0120 (7)	−0.0030 (6)
F2	0.0684 (10)	0.0713 (9)	0.0762 (10)	−0.0407 (8)	−0.0092 (8)	0.0186 (8)
F3	0.0660 (9)	0.0505 (7)	0.0522 (8)	−0.0012 (6)	0.0009 (6)	−0.0103 (6)
F4	0.1027 (13)	0.0488 (8)	0.0953 (12)	−0.0170 (8)	0.0076 (10)	−0.0338 (8)
F5	0.0411 (7)	0.0681 (9)	0.0810 (10)	−0.0061 (7)	−0.0176 (7)	−0.0021 (7)
F6	0.0645 (10)	0.0933 (11)	0.0712 (10)	−0.0101 (8)	−0.0323 (8)	−0.0034 (8)
F7	0.1060 (16)	0.0544 (10)	0.0472 (8)	−0.0440 (10)	0.0139 (9)	−0.0034 (7)
F8	0.0848 (13)	0.0779 (12)	0.0403 (8)	−0.0513 (11)	−0.0114 (8)	0.0051 (7)
F9	0.0768 (14)	0.147 (2)	0.0720 (12)	−0.0489 (15)	−0.0441 (11)	0.0290 (13)
F10	0.0460 (9)	0.0799 (12)	0.0874 (13)	−0.0163 (9)	−0.0181 (8)	−0.0023 (9)
F11	0.1291 (19)	0.0509 (10)	0.0623 (11)	−0.0183 (11)	0.0139 (11)	−0.0177 (8)
F12	0.1068 (16)	0.0556 (10)	0.0522 (10)	0.0220 (10)	0.0062 (10)	−0.0086 (7)
F13	0.060 (4)	0.074 (4)	0.083 (4)	0.000 (3)	−0.015 (3)	−0.021 (3)
F14	0.060 (4)	0.074 (4)	0.083 (4)	0.000 (3)	−0.015 (3)	−0.021 (3)
F15	0.060 (4)	0.074 (4)	0.083 (4)	0.000 (3)	−0.015 (3)	−0.021 (3)
F16	0.060 (4)	0.074 (4)	0.083 (4)	0.000 (3)	−0.015 (3)	−0.021 (3)
F17	0.060 (4)	0.074 (4)	0.083 (4)	0.000 (3)	−0.015 (3)	−0.021 (3)
F18	0.060 (4)	0.074 (4)	0.083 (4)	0.000 (3)	−0.015 (3)	−0.021 (3)
O1	0.0596 (10)	0.0479 (8)	0.0317 (7)	−0.0174 (7)	0.0028 (6)	−0.0053 (6)
O2	0.0547 (9)	0.0445 (8)	0.0304 (7)	−0.0119 (7)	−0.0036 (6)	−0.0047 (6)
O21	0.0595 (10)	0.0513 (9)	0.0328 (7)	−0.0163 (7)	−0.0104 (7)	0.0023 (6)
O22	0.0552 (9)	0.0532 (9)	0.0307 (7)	−0.0141 (7)	−0.0047 (6)	0.0002 (6)
N1	0.0286 (8)	0.0269 (7)	0.0291 (7)	−0.0064 (6)	−0.0009 (6)	−0.0032 (5)
N2	0.0284 (8)	0.0308 (8)	0.0439 (9)	−0.0033 (6)	−0.0050 (7)	0.0007 (6)
N3	0.0311 (8)	0.0282 (7)	0.0341 (8)	−0.0027 (6)	−0.0040 (6)	−0.0014 (6)
N21	0.0303 (8)	0.0288 (7)	0.0307 (8)	−0.0066 (6)	−0.0048 (6)	−0.0016 (6)
N22	0.0308 (8)	0.0299 (7)	0.0365 (8)	−0.0025 (6)	−0.0035 (6)	−0.0032 (6)
N23	0.0298 (8)	0.0364 (8)	0.0414 (9)	−0.0018 (7)	−0.0053 (7)	−0.0078 (7)
C1	0.0287 (9)	0.0266 (8)	0.0359 (9)	−0.0067 (7)	−0.0025 (7)	−0.0012 (7)
C2	0.0306 (10)	0.0299 (9)	0.0378 (10)	−0.0073 (7)	−0.0019 (8)	−0.0014 (7)
C3	0.0312 (10)	0.0293 (8)	0.0317 (9)	−0.0065 (7)	−0.0029 (7)	−0.0015 (7)
C4	0.0369 (11)	0.0299 (9)	0.0542 (12)	−0.0030 (8)	−0.0016 (9)	0.0027 (8)
C5	0.0297 (10)	0.0447 (11)	0.0526 (12)	−0.0043 (9)	−0.0106 (9)	−0.0004 (9)
C6	0.0293 (10)	0.0348 (10)	0.0553 (12)	−0.0030 (8)	−0.0095 (9)	−0.0039 (8)
C7	0.0446 (11)	0.0289 (9)	0.0394 (10)	0.0007 (8)	−0.0068 (9)	0.0003 (7)
C8	0.0334 (10)	0.0293 (9)	0.0328 (9)	−0.0043 (7)	−0.0018 (7)	−0.0051 (7)
C9	0.0293 (9)	0.0278 (8)	0.0313 (9)	−0.0018 (7)	−0.0013 (7)	−0.0006 (7)
C10	0.0309 (10)	0.0269 (8)	0.0401 (10)	−0.0031 (7)	−0.0043 (8)	−0.0041 (7)
C11	0.0267 (9)	0.0254 (8)	0.0393 (10)	−0.0021 (7)	−0.0020 (7)	0.0002 (7)
C12	0.0326 (10)	0.0318 (9)	0.0503 (12)	−0.0036 (8)	0.0016 (9)	0.0045 (8)
C13	0.0315 (10)	0.0273 (9)	0.0757 (16)	−0.0060 (8)	0.0016 (10)	0.0019 (9)
C14	0.0354 (11)	0.0287 (9)	0.0786 (16)	−0.0054 (8)	−0.0135 (10)	−0.0096 (9)
C15	0.0432 (12)	0.0321 (9)	0.0505 (12)	−0.0050 (9)	−0.0111 (9)	−0.0085 (8)
C21	0.0314 (9)	0.0285 (8)	0.0357 (9)	−0.0070 (7)	−0.0045 (7)	−0.0031 (7)
C22	0.0319 (10)	0.0305 (9)	0.0350 (9)	−0.0067 (7)	−0.0041 (7)	−0.0034 (7)
C23	0.0332 (10)	0.0333 (9)	0.0368 (10)	−0.0069 (8)	−0.0044 (8)	−0.0054 (7)
C24	0.0282 (10)	0.0383 (10)	0.0525 (12)	−0.0061 (8)	0.0003 (8)	0.0012 (9)
C25	0.0414 (11)	0.0336 (10)	0.0466 (11)	0.0015 (8)	−0.0046 (9)	−0.0090 (8)
C26	0.0421 (12)	0.0350 (10)	0.0542 (13)	0.0007 (9)	−0.0015 (10)	−0.0078 (9)
C27	0.0311 (11)	0.0532 (12)	0.0490 (12)	−0.0038 (9)	−0.0012 (9)	−0.0090 (9)
C28	0.0340 (10)	0.0320 (9)	0.0343 (10)	−0.0028 (8)	−0.0042 (8)	−0.0010 (7)
C29	0.0302 (9)	0.0333 (9)	0.0334 (9)	−0.0017 (8)	−0.0046 (7)	−0.0049 (7)
C30	0.0319 (10)	0.0265 (8)	0.0426 (10)	−0.0025 (7)	−0.0049 (8)	−0.0001 (7)
C31	0.0280 (9)	0.0292 (9)	0.0414 (10)	0.0003 (7)	−0.0060 (8)	−0.0065 (7)
C32	0.0343 (11)	0.0392 (10)	0.0513 (12)	−0.0010 (8)	−0.0092 (9)	−0.0149 (9)
C33	0.0340 (11)	0.0354 (10)	0.0796 (17)	−0.0022 (9)	−0.0115 (11)	−0.0207 (10)
C34	0.0352 (11)	0.0278 (9)	0.0848 (18)	−0.0060 (8)	−0.0022 (11)	−0.0057 (10)
C35	0.0405 (11)	0.0307 (9)	0.0572 (13)	−0.0067 (8)	−0.0008 (9)	0.0015 (9)

Geometric parameters (Å, º)

P1—F4	1.5767 (15)	C5—H5B	0.9800
P1—F2	1.5785 (13)	C5—H5C	0.9800
P1—F6	1.5822 (15)	C6—H6A	0.9800
P1—F1	1.5983 (13)	C6—H6B	0.9800
P1—F5	1.5997 (14)	C6—H6C	0.9800
P1—F3	1.6045 (14)	C7—H7C	0.9800
P2—F16	1.421 (14)	C7—H7B	0.9800
P2—F13	1.548 (14)	C7—H7A	0.9800
P2—F9	1.5603 (18)	C8—C10	1.485 (2)
P2—F12	1.5620 (17)	C9—C11	1.485 (2)
P2—F15	1.566 (14)	C10—C15	1.386 (3)
P2—F7	1.5709 (14)	C10—C11	1.388 (3)
P2—F14	1.583 (14)	C11—C12	1.382 (2)
P2—F10	1.6024 (17)	C12—C13	1.396 (3)
P2—F17	1.604 (14)	C12—H12	0.9500
P2—F8	1.6072 (15)	C13—C14	1.386 (3)
P2—F18	1.614 (14)	C13—H13	0.9500
P2—F11	1.6180 (18)	C14—C15	1.382 (3)
O1—C8	1.205 (2)	C14—H14	0.9500
O2—C9	1.204 (2)	C15—H15	0.9500
O21—C28	1.204 (2)	C21—C23	1.401 (3)
O22—C29	1.205 (2)	C21—C22	1.404 (2)
N1—C8	1.406 (2)	C22—H22A	0.9500
N1—C9	1.413 (2)	C23—H23A	0.9500
N1—C1	1.421 (2)	C24—H24A	0.9800
N2—C2	1.313 (2)	C24—H24B	0.9800
N2—C5	1.464 (2)	C24—H24C	0.9800
N2—C4	1.468 (2)	C25—H25A	0.9800
N3—C3	1.304 (2)	C25—H25B	0.9800
N3—C6	1.461 (2)	C25—H25C	0.9800
N3—C7	1.467 (2)	C26—H26A	0.9800
N21—C28	1.403 (2)	C26—H26B	0.9800
N21—C29	1.408 (2)	C26—H26C	0.9800
N21—C21	1.425 (2)	C27—H27A	0.9800
N22—C22	1.306 (2)	C27—H27B	0.9800
N22—C24	1.465 (2)	C27—H27C	0.9800
N22—C25	1.475 (2)	C28—C30	1.484 (3)
N23—C23	1.306 (2)	C29—C31	1.484 (2)
N23—C26	1.465 (2)	C30—C35	1.381 (3)
N23—C27	1.467 (2)	C30—C31	1.394 (3)
C1—C2	1.397 (3)	C31—C32	1.381 (3)
C1—C3	1.406 (2)	C32—C33	1.392 (3)
C2—H2A	0.9500	C32—H32	0.9500
C3—H3A	0.9500	C33—C34	1.383 (3)
C4—H4A	0.9800	C33—H33	0.9500
C4—H4B	0.9800	C34—C35	1.395 (3)
C4—H4C	0.9800	C34—H34	0.9500
C5—H5A	0.9800	C35—H35	0.9500
F4—P1—F2	91.12 (9)	H6B—C6—H6C	109.5
F4—P1—F6	90.39 (10)	N3—C7—H7C	109.5
F2—P1—F6	90.33 (8)	N3—C7—H7B	109.5
F4—P1—F1	89.43 (8)	H7C—C7—H7B	109.5
F2—P1—F1	178.29 (9)	N3—C7—H7A	109.5
F6—P1—F1	91.28 (9)	H7C—C7—H7A	109.5
F4—P1—F5	91.47 (9)	H7B—C7—H7A	109.5
F2—P1—F5	89.32 (8)	O1—C8—N1	124.73 (16)
F6—P1—F5	178.11 (9)	O1—C8—C10	129.63 (17)
F1—P1—F5	89.04 (8)	N1—C8—C10	105.61 (14)
F4—P1—F3	178.18 (8)	O2—C9—N1	124.20 (16)
F2—P1—F3	90.69 (8)	O2—C9—C11	130.21 (16)
F6—P1—F3	89.77 (9)	N1—C9—C11	105.58 (14)
F1—P1—F3	88.76 (7)	C15—C10—C11	121.35 (17)
F5—P1—F3	88.38 (8)	C15—C10—C8	129.93 (17)
F16—P2—F13	90.5 (8)	C11—C10—C8	108.67 (15)
F9—P2—F12	95.60 (15)	C12—C11—C10	121.60 (17)
F16—P2—F15	82.2 (8)	C12—C11—C9	129.94 (18)
F13—P2—F15	172.6 (8)	C10—C11—C9	108.43 (14)
F9—P2—F7	91.25 (11)	C11—C12—C13	117.0 (2)
F12—P2—F7	90.93 (9)	C11—C12—H12	121.5
F16—P2—F14	97.4 (8)	C13—C12—H12	121.5
F13—P2—F14	93.0 (8)	C14—C13—C12	121.14 (18)
F15—P2—F14	89.6 (8)	C14—C13—H13	119.4
F9—P2—F10	175.05 (12)	C12—C13—H13	119.4
F12—P2—F10	88.30 (11)	C15—C14—C13	121.65 (19)
F7—P2—F10	91.72 (10)	C15—C14—H14	119.2
F16—P2—F17	89.1 (8)	C13—C14—H14	119.2
F13—P2—F17	90.5 (7)	C14—C15—C10	117.2 (2)
F15—P2—F17	87.7 (7)	C14—C15—H15	121.4
F14—P2—F17	172.6 (8)	C10—C15—H15	121.4
F9—P2—F8	89.28 (10)	C23—C21—C22	114.75 (15)
F12—P2—F8	90.83 (10)	C23—C21—N21	123.10 (16)
F7—P2—F8	178.10 (11)	C22—C21—N21	122.08 (16)
F10—P2—F8	87.63 (9)	N22—C22—C21	131.53 (16)
F16—P2—F18	176.8 (8)	N22—C22—H22A	114.2
F13—P2—F18	92.7 (8)	C21—C22—H22A	114.2
F15—P2—F18	94.6 (8)	N23—C23—C21	131.43 (17)
F14—P2—F18	82.9 (8)	N23—C23—H23A	114.3
F17—P2—F18	90.4 (7)	C21—C23—H23A	114.3
F9—P2—F11	87.58 (13)	N22—C24—H24A	109.5
F12—P2—F11	176.63 (12)	N22—C24—H24B	109.5
F7—P2—F11	90.12 (9)	H24A—C24—H24B	109.5
F10—P2—F11	88.47 (12)	N22—C24—H24C	109.5
F8—P2—F11	88.08 (9)	H24A—C24—H24C	109.5
C8—N1—C9	111.69 (13)	H24B—C24—H24C	109.5
C8—N1—C1	124.06 (14)	N22—C25—H25A	109.5
C9—N1—C1	124.07 (14)	N22—C25—H25B	109.5
C2—N2—C5	119.03 (15)	H25A—C25—H25B	109.5
C2—N2—C4	125.57 (16)	N22—C25—H25C	109.5
C5—N2—C4	115.39 (15)	H25A—C25—H25C	109.5
C3—N3—C6	125.35 (15)	H25B—C25—H25C	109.5
C3—N3—C7	119.46 (15)	N23—C26—H26A	109.5
C6—N3—C7	114.73 (15)	N23—C26—H26B	109.5
C28—N21—C29	111.95 (14)	H26A—C26—H26B	109.5
C28—N21—C21	124.05 (15)	N23—C26—H26C	109.5
C29—N21—C21	123.84 (14)	H26A—C26—H26C	109.5
C22—N22—C24	125.96 (16)	H26B—C26—H26C	109.5
C22—N22—C25	119.20 (16)	N23—C27—H27A	109.5
C24—N22—C25	114.60 (16)	N23—C27—H27B	109.5
C23—N23—C26	125.48 (16)	H27A—C27—H27B	109.5
C23—N23—C27	119.43 (16)	N23—C27—H27C	109.5
C26—N23—C27	115.08 (16)	H27A—C27—H27C	109.5
C2—C1—C3	114.43 (15)	H27B—C27—H27C	109.5
C2—C1—N1	123.21 (16)	O21—C28—N21	124.46 (17)
C3—C1—N1	122.30 (16)	O21—C28—C30	129.77 (17)
N2—C2—C1	131.96 (16)	N21—C28—C30	105.77 (15)
N2—C2—H2A	114.0	O22—C29—N21	124.88 (17)
C1—C2—H2A	114.0	O22—C29—C31	129.59 (17)
N3—C3—C1	131.78 (16)	N21—C29—C31	105.51 (14)
N3—C3—H3A	114.1	C35—C30—C31	121.15 (18)
C1—C3—H3A	114.1	C35—C30—C28	130.55 (18)
N2—C4—H4A	109.5	C31—C30—C28	108.25 (15)
N2—C4—H4B	109.5	C32—C31—C30	121.72 (17)
H4A—C4—H4B	109.5	C32—C31—C29	129.74 (18)
N2—C4—H4C	109.5	C30—C31—C29	108.50 (15)
H4A—C4—H4C	109.5	C31—C32—C33	117.0 (2)
H4B—C4—H4C	109.5	C31—C32—H32	121.5
N2—C5—H5A	109.5	C33—C32—H32	121.5
N2—C5—H5B	109.5	C34—C33—C32	121.50 (19)
H5A—C5—H5B	109.5	C34—C33—H33	119.3
N2—C5—H5C	109.5	C32—C33—H33	119.3
H5A—C5—H5C	109.5	C33—C34—C35	121.30 (19)
H5B—C5—H5C	109.5	C33—C34—H34	119.3
N3—C6—H6A	109.5	C35—C34—H34	119.3
N3—C6—H6B	109.5	C30—C35—C34	117.3 (2)
H6A—C6—H6B	109.5	C30—C35—H35	121.4
N3—C6—H6C	109.5	C34—C35—H35	121.4
H6A—C6—H6C	109.5
C8—N1—C1—C2	98.2 (2)	C28—N21—C21—C23	−101.8 (2)
C9—N1—C1—C2	−86.9 (2)	C29—N21—C21—C23	83.2 (2)
C8—N1—C1—C3	−84.7 (2)	C28—N21—C21—C22	81.3 (2)
C9—N1—C1—C3	90.1 (2)	C29—N21—C21—C22	−93.6 (2)
C5—N2—C2—C1	−179.6 (2)	C24—N22—C22—C21	1.0 (3)
C4—N2—C2—C1	−0.7 (3)	C25—N22—C22—C21	175.03 (18)
C3—C1—C2—N2	−176.71 (19)	C23—C21—C22—N22	−177.07 (19)
N1—C1—C2—N2	0.6 (3)	N21—C21—C22—N22	0.0 (3)
C6—N3—C3—C1	−2.1 (3)	C26—N23—C23—C21	2.5 (3)
C7—N3—C3—C1	−173.96 (19)	C27—N23—C23—C21	−176.0 (2)
C2—C1—C3—N3	178.06 (19)	C22—C21—C23—N23	178.97 (19)
N1—C1—C3—N3	0.8 (3)	N21—C21—C23—N23	1.9 (3)
C9—N1—C8—O1	−179.49 (19)	C29—N21—C28—O21	−179.08 (19)
C1—N1—C8—O1	−4.1 (3)	C21—N21—C28—O21	5.4 (3)
C9—N1—C8—C10	−1.2 (2)	C29—N21—C28—C30	1.7 (2)
C1—N1—C8—C10	174.25 (16)	C21—N21—C28—C30	−173.81 (16)
C8—N1—C9—O2	−179.93 (18)	C28—N21—C29—O22	179.88 (18)
C1—N1—C9—O2	4.6 (3)	C21—N21—C29—O22	−4.6 (3)
C8—N1—C9—C11	0.82 (19)	C28—N21—C29—C31	−1.3 (2)
C1—N1—C9—C11	−174.61 (15)	C21—N21—C29—C31	174.19 (15)
O1—C8—C10—C15	1.9 (4)	O21—C28—C30—C35	−3.3 (4)
N1—C8—C10—C15	−176.25 (19)	N21—C28—C30—C35	175.8 (2)
O1—C8—C10—C11	179.3 (2)	O21—C28—C30—C31	179.4 (2)
N1—C8—C10—C11	1.1 (2)	N21—C28—C30—C31	−1.4 (2)
C15—C10—C11—C12	−1.0 (3)	C35—C30—C31—C32	1.1 (3)
C8—C10—C11—C12	−178.60 (17)	C28—C30—C31—C32	178.65 (18)
C15—C10—C11—C9	177.00 (17)	C35—C30—C31—C29	−176.92 (18)
C8—C10—C11—C9	−0.6 (2)	C28—C30—C31—C29	0.6 (2)
O2—C9—C11—C12	−1.5 (3)	O22—C29—C31—C32	1.3 (3)
N1—C9—C11—C12	177.66 (18)	N21—C29—C31—C32	−177.44 (19)
O2—C9—C11—C10	−179.3 (2)	O22—C29—C31—C30	179.1 (2)
N1—C9—C11—C10	−0.1 (2)	N21—C29—C31—C30	0.4 (2)
C10—C11—C12—C13	2.1 (3)	C30—C31—C32—C33	−2.0 (3)
C9—C11—C12—C13	−175.43 (18)	C29—C31—C32—C33	175.61 (19)
C11—C12—C13—C14	−1.4 (3)	C31—C32—C33—C34	1.0 (3)
C12—C13—C14—C15	−0.5 (3)	C32—C33—C34—C35	0.8 (3)
C13—C14—C15—C10	1.6 (3)	C31—C30—C35—C34	0.7 (3)
C11—C10—C15—C14	−0.9 (3)	C28—C30—C35—C34	−176.2 (2)
C8—C10—C15—C14	176.19 (19)	C33—C34—C35—C30	−1.7 (3)