The title compound, C20H24Cl4N5O3P3·0.5C6H6, is a novel crypta-phosphazene derivative containing three ether O and two N atoms in the macrocycle. The cavity radius of the macrocycle is estimated to be approximately 1.52 Å. The benzene solvent molecule lies on a crystallographic twofold rotation axis.
Supporting information
CCDC reference: 248827
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- R factor = 0.067
- wR factor = 0.197
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C
RADNW01_ALERT_1_C The radiation wavelength lies outside the expected range
for the supplied radiation type. Expected range 1.54175-1.54180
Wavelength given = 1.54184
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for N2
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for P2
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for P3
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for C22
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C21 -C22_a 1.36 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT733_ALERT_1_C Torsion Calc -0.9(13), Rep -0.9(6) ...... 2.17 su-Rat
C22 -C23 -C24 -C23 1.555 1.555 1.555 2.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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 (Farrugia, 1999).
4,4,6,6-Tetrachloro-1',3'-[2,2'-(3-oxapentane-1,5-dioxy)dibenzyl]-
2
λ5,4
λ5,6
λ5-cyclotriphosphazene-2-spiro-2'-1,3,2-diazaphospholane
benzene hemisolvate
top
Crystal data top
C20H24Cl4N5O3P3·0.5C6H6 | F(000) = 2696 |
Mr = 656.23 | Dx = 1.463 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 18.531 (5) Å | θ = 12–22° |
b = 13.431 (3) Å | µ = 5.43 mm−1 |
c = 24.043 (4) Å | T = 293 K |
β = 95.23 (2)° | Prism, colourless |
V = 5959 (2) Å3 | 0.40 × 0.25 × 0.25 mm |
Z = 8 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.041 |
Radiation source: fine-focus sealed tube | θmax = 74.2°, θmin = 3.7° |
Graphite monochromator | h = 0→23 |
non–profiled ω scans | k = 0→16 |
10505 measured reflections | l = −30→29 |
5913 independent reflections | 3 standard reflections every 120 min |
3612 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.067 | H-atom parameters constrained |
wR(F2) = 0.197 | w = 1/[σ2(Fo2) + (0.1326P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5113 reflections | Δρmax = 0.50 e Å−3 |
335 parameters | Δρmin = −1.24 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0023 (2) |
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 | |
Cl1 | 0.18455 (11) | 0.36564 (16) | 0.01082 (7) | 0.0928 (6) | |
Cl2 | 0.16173 (9) | 0.21150 (10) | 0.10186 (9) | 0.0849 (6) | |
Cl3 | 0.00671 (10) | 0.58454 (13) | 0.06979 (6) | 0.0784 (5) | |
Cl4 | −0.02169 (9) | 0.45905 (15) | 0.16988 (8) | 0.0859 (6) | |
P1 | 0.20612 (5) | 0.51202 (8) | 0.16243 (4) | 0.0352 (3) | |
P2 | 0.05930 (6) | 0.48955 (9) | 0.12323 (5) | 0.0397 (3) | |
P3 | 0.15737 (7) | 0.35847 (9) | 0.09037 (5) | 0.0468 (3) | |
O1 | 0.3254 (2) | 0.3245 (3) | 0.25836 (15) | 0.0618 (10) | |
O2 | 0.4012 (2) | 0.3322 (3) | 0.15829 (16) | 0.0653 (10) | |
O3 | 0.36608 (19) | 0.4961 (3) | 0.07973 (15) | 0.0552 (9) | |
N1 | 0.1214 (2) | 0.5437 (3) | 0.15906 (17) | 0.0492 (10) | |
N2 | 0.0763 (2) | 0.3929 (3) | 0.0894 (2) | 0.0665 (14) | |
N3 | 0.2172 (2) | 0.4094 (3) | 0.13068 (17) | 0.0450 (9) | |
N4 | 0.2567 (2) | 0.6009 (3) | 0.14250 (14) | 0.0427 (9) | |
N5 | 0.2423 (2) | 0.5098 (3) | 0.22658 (15) | 0.0445 (9) | |
C1 | 0.2116 (3) | 0.4522 (4) | 0.26982 (19) | 0.0529 (12) | |
C2 | 0.2657 (3) | 0.4275 (4) | 0.3178 (2) | 0.0521 (12) | |
C3 | 0.2611 (4) | 0.4682 (5) | 0.3702 (2) | 0.0688 (16) | |
C4 | 0.3098 (5) | 0.4457 (5) | 0.4144 (2) | 0.080 (2) | |
C5 | 0.3654 (5) | 0.3803 (6) | 0.4081 (2) | 0.084 (2) | |
C6 | 0.3735 (4) | 0.3369 (5) | 0.3556 (2) | 0.0705 (17) | |
C7 | 0.3230 (3) | 0.3606 (4) | 0.3112 (2) | 0.0552 (13) | |
C8 | 0.3841 (4) | 0.2622 (5) | 0.2463 (3) | 0.0711 (16) | |
C9 | 0.3770 (4) | 0.2454 (4) | 0.1846 (3) | 0.0710 (16) | |
C10 | 0.3899 (3) | 0.3261 (4) | 0.0996 (2) | 0.0614 (14) | |
C11 | 0.4178 (3) | 0.4194 (4) | 0.0752 (2) | 0.0631 (15) | |
C12 | 0.3844 (3) | 0.5905 (4) | 0.06564 (17) | 0.0448 (10) | |
C13 | 0.4523 (3) | 0.6180 (4) | 0.05010 (19) | 0.0542 (13) | |
C14 | 0.4647 (3) | 0.7178 (5) | 0.0373 (2) | 0.0629 (15) | |
C15 | 0.4119 (4) | 0.7873 (5) | 0.0403 (2) | 0.0687 (17) | |
C16 | 0.3436 (3) | 0.7595 (4) | 0.0556 (2) | 0.0572 (13) | |
C17 | 0.3291 (3) | 0.6622 (4) | 0.06839 (17) | 0.0441 (10) | |
C18 | 0.2556 (3) | 0.6340 (4) | 0.08470 (18) | 0.0456 (10) | |
C19 | 0.3059 (3) | 0.6419 (4) | 0.1876 (2) | 0.0536 (12) | |
C20 | 0.2878 (3) | 0.5949 (4) | 0.2402 (2) | 0.0591 (14) | |
C21 | 0.0000 | 0.2242 (8) | 0.2500 | 0.089 | |
C22 | 0.0153 (4) | 0.1726 (4) | 0.2020 (3) | 0.066 | |
C23 | 0.0159 (6) | 0.0793 (9) | 0.2030 (5) | 0.129 (4) | |
C24 | 0.0000 | 0.0252 (9) | 0.2500 | 0.165 (10) | |
H1A | 0.1916 | 0.3908 | 0.2536 | 0.063* | |
H1B | 0.1721 | 0.4896 | 0.2836 | 0.063* | |
H3 | 0.2236 | 0.5122 | 0.3754 | 0.083* | |
H4 | 0.3053 | 0.4748 | 0.4490 | 0.097* | |
H5 | 0.3980 | 0.3646 | 0.4385 | 0.100* | |
H6 | 0.4117 | 0.2936 | 0.3508 | 0.085* | |
H8A | 0.3820 | 0.1993 | 0.2659 | 0.085* | |
H8B | 0.4300 | 0.2941 | 0.2579 | 0.085* | |
H9A | 0.4059 | 0.1885 | 0.1755 | 0.085* | |
H9B | 0.3268 | 0.2320 | 0.1716 | 0.085* | |
H10A | 0.3386 | 0.3185 | 0.0881 | 0.074* | |
H10B | 0.4152 | 0.2688 | 0.0863 | 0.074* | |
H11A | 0.4637 | 0.4381 | 0.0951 | 0.076* | |
H11B | 0.4255 | 0.4088 | 0.0362 | 0.076* | |
H13 | 0.4887 | 0.5708 | 0.0483 | 0.065* | |
H14 | 0.5096 | 0.7368 | 0.0265 | 0.075* | |
H15 | 0.4211 | 0.8535 | 0.0321 | 0.082* | |
H16 | 0.3076 | 0.8075 | 0.0571 | 0.069* | |
H18A | 0.2235 | 0.6909 | 0.0792 | 0.055* | |
H18B | 0.2360 | 0.5811 | 0.0603 | 0.055* | |
H19A | 0.3000 | 0.7135 | 0.1896 | 0.064* | |
H19B | 0.3557 | 0.6275 | 0.1811 | 0.064* | |
H20A | 0.3318 | 0.5743 | 0.2621 | 0.071* | |
H20B | 0.2626 | 0.6422 | 0.2620 | 0.071* | |
H21 | 0.0000 | 0.2934 | 0.2500 | 0.107* | |
H22 | 0.0249 | 0.2069 | 0.1699 | 0.079* | |
H23 | 0.0272 | 0.0449 | 0.1714 | 0.155* | |
H24 | 0.0000 | −0.0441 | 0.2500 | 0.198* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1061 (14) | 0.1183 (15) | 0.0525 (8) | 0.0094 (11) | −0.0004 (8) | −0.0300 (9) |
Cl2 | 0.0740 (10) | 0.0394 (7) | 0.1373 (15) | 0.0036 (6) | −0.0119 (10) | −0.0131 (8) |
Cl3 | 0.0900 (11) | 0.0803 (10) | 0.0614 (8) | 0.0286 (8) | −0.0120 (7) | 0.0174 (7) |
Cl4 | 0.0593 (9) | 0.1031 (13) | 0.1002 (12) | −0.0058 (8) | 0.0332 (8) | 0.0213 (10) |
P1 | 0.0348 (5) | 0.0389 (6) | 0.0310 (5) | 0.0018 (4) | −0.0023 (4) | −0.0055 (4) |
P3 | 0.0424 (6) | 0.0419 (6) | 0.0539 (7) | 0.0030 (5) | −0.0076 (5) | −0.0147 (5) |
P2 | 0.0316 (5) | 0.0433 (6) | 0.0433 (6) | 0.0029 (4) | −0.0008 (4) | 0.0001 (4) |
N1 | 0.041 (2) | 0.049 (2) | 0.057 (2) | 0.0043 (17) | −0.0002 (17) | −0.0185 (19) |
N2 | 0.042 (2) | 0.052 (3) | 0.100 (4) | 0.0074 (19) | −0.020 (2) | −0.033 (2) |
N3 | 0.0375 (19) | 0.040 (2) | 0.056 (2) | 0.0068 (15) | −0.0036 (16) | −0.0165 (17) |
N4 | 0.047 (2) | 0.050 (2) | 0.0296 (18) | −0.0091 (17) | −0.0041 (15) | −0.0011 (15) |
N5 | 0.051 (2) | 0.050 (2) | 0.0314 (17) | −0.0075 (17) | 0.0011 (15) | 0.0006 (15) |
O1 | 0.067 (2) | 0.064 (2) | 0.054 (2) | 0.0083 (19) | −0.0033 (17) | 0.0076 (17) |
O2 | 0.079 (3) | 0.057 (2) | 0.060 (2) | −0.004 (2) | 0.0130 (19) | 0.0038 (17) |
O3 | 0.0523 (19) | 0.054 (2) | 0.061 (2) | 0.0060 (16) | 0.0176 (16) | 0.0095 (16) |
C1 | 0.054 (3) | 0.065 (3) | 0.039 (2) | −0.007 (2) | 0.001 (2) | 0.010 (2) |
C2 | 0.059 (3) | 0.060 (3) | 0.037 (2) | −0.014 (2) | −0.003 (2) | 0.009 (2) |
C3 | 0.103 (5) | 0.068 (4) | 0.036 (3) | −0.013 (3) | 0.010 (3) | 0.009 (2) |
C4 | 0.127 (6) | 0.072 (4) | 0.039 (3) | −0.029 (4) | −0.010 (3) | 0.007 (3) |
C5 | 0.109 (6) | 0.096 (5) | 0.040 (3) | −0.038 (4) | −0.028 (3) | 0.024 (3) |
C6 | 0.074 (4) | 0.079 (4) | 0.056 (3) | −0.009 (3) | −0.010 (3) | 0.025 (3) |
C7 | 0.068 (3) | 0.058 (3) | 0.038 (2) | −0.012 (3) | −0.005 (2) | 0.014 (2) |
C8 | 0.079 (4) | 0.054 (3) | 0.081 (4) | 0.011 (3) | 0.013 (3) | 0.020 (3) |
C9 | 0.088 (4) | 0.042 (3) | 0.086 (4) | 0.003 (3) | 0.019 (3) | 0.005 (3) |
C10 | 0.065 (3) | 0.059 (3) | 0.062 (3) | 0.014 (3) | 0.014 (3) | −0.005 (3) |
C11 | 0.066 (3) | 0.067 (4) | 0.059 (3) | 0.022 (3) | 0.021 (3) | −0.002 (3) |
C12 | 0.055 (3) | 0.054 (3) | 0.0252 (19) | −0.002 (2) | 0.0020 (18) | 0.0014 (18) |
C13 | 0.053 (3) | 0.079 (4) | 0.031 (2) | −0.005 (3) | 0.003 (2) | 0.000 (2) |
C14 | 0.067 (3) | 0.083 (4) | 0.039 (3) | −0.027 (3) | 0.007 (2) | −0.011 (3) |
C15 | 0.091 (5) | 0.066 (4) | 0.049 (3) | −0.034 (3) | 0.010 (3) | −0.002 (3) |
C16 | 0.072 (3) | 0.053 (3) | 0.048 (3) | −0.007 (3) | 0.012 (2) | 0.000 (2) |
C17 | 0.051 (2) | 0.055 (3) | 0.027 (2) | −0.002 (2) | 0.0015 (18) | 0.0022 (18) |
C18 | 0.047 (2) | 0.057 (3) | 0.032 (2) | 0.005 (2) | −0.0027 (18) | 0.0047 (18) |
C19 | 0.059 (3) | 0.061 (3) | 0.039 (2) | −0.021 (2) | −0.007 (2) | −0.002 (2) |
C20 | 0.067 (3) | 0.073 (4) | 0.035 (2) | −0.022 (3) | −0.007 (2) | −0.007 (2) |
C21 | 0.088 | 0.078 | 0.105 | 0.000 | 0.026 | 0.000 |
C22 | 0.079 | 0.055 | 0.063 | −0.022 | 0.006 | −0.005 |
C23 | 0.105 (7) | 0.148 (10) | 0.125 (8) | 0.033 (7) | −0.038 (6) | −0.070 (7) |
C24 | 0.137 (13) | 0.048 (6) | 0.29 (3) | 0.000 | −0.095 (17) | 0.000 |
Geometric parameters (Å, º) top
C21—C22i | 1.396 (8) | C12—C17 | 1.412 (7) |
C21—C22 | 1.396 (8) | O1—C7 | 1.363 (6) |
C21—H21 | 0.9300 | O1—C8 | 1.424 (7) |
C23—C22 | 1.254 (12) | C2—C3 | 1.382 (7) |
C23—C24 | 1.396 (14) | C2—C7 | 1.411 (8) |
C23—H23 | 0.9300 | C2—C1 | 1.496 (7) |
C22—H22 | 0.9300 | C16—C17 | 1.376 (7) |
C24—C23i | 1.396 (14) | C16—C15 | 1.401 (9) |
C24—H24 | 0.9300 | C16—H16 | 0.9300 |
O2—C10 | 1.411 (7) | C19—C20 | 1.478 (7) |
O2—C9 | 1.419 (7) | C19—H19A | 0.9700 |
C10—C11 | 1.496 (8) | C19—H19B | 0.9700 |
C10—H10A | 0.9700 | C7—C6 | 1.393 (7) |
C10—H10B | 0.9700 | N5—C20 | 1.440 (6) |
C11—O3 | 1.418 (6) | N5—C1 | 1.453 (6) |
C11—H11A | 0.9700 | C8—C9 | 1.495 (9) |
C11—H11B | 0.9700 | C8—H8A | 0.9700 |
P1—N3 | 1.598 (4) | C8—H8B | 0.9700 |
P1—N4 | 1.617 (4) | C13—C14 | 1.398 (8) |
P1—N1 | 1.622 (4) | C13—H13 | 0.9300 |
P1—N5 | 1.625 (4) | C15—C14 | 1.359 (9) |
P3—N3 | 1.562 (4) | C15—H15 | 0.9300 |
P3—N2 | 1.570 (4) | C1—H1A | 0.9700 |
P3—Cl2 | 1.9939 (19) | C1—H1B | 0.9700 |
P3—Cl1 | 2.024 (2) | C6—C5 | 1.410 (10) |
P2—N1 | 1.553 (4) | C6—H6 | 0.9300 |
P2—N2 | 1.579 (4) | C20—H20A | 0.9700 |
P2—Cl4 | 1.9964 (19) | C20—H20B | 0.9700 |
P2—Cl3 | 1.9999 (18) | C3—C4 | 1.365 (9) |
N4—C18 | 1.457 (6) | C3—H3 | 0.9300 |
N4—C19 | 1.459 (6) | C14—H14 | 0.9300 |
C18—C17 | 1.500 (7) | C5—C4 | 1.374 (11) |
C18—H18A | 0.9700 | C5—H5 | 0.9300 |
C18—H18B | 0.9700 | C9—H9A | 0.9700 |
O3—C12 | 1.364 (6) | C9—H9B | 0.9700 |
C12—C13 | 1.394 (7) | C4—H4 | 0.9300 |
| | | |
C22i—C21—C22 | 120.5 (10) | C17—C16—H16 | 119.6 |
C22i—C21—H21 | 119.7 | C15—C16—H16 | 119.6 |
C22—C21—H21 | 119.7 | N4—C19—C20 | 107.5 (4) |
C22—C23—C24 | 122.3 (10) | N4—C19—H19A | 110.2 |
C22—C23—H23 | 118.9 | C20—C19—H19A | 110.2 |
C24—C23—H23 | 118.9 | N4—C19—H19B | 110.2 |
C23—C22—C21 | 118.8 (8) | C20—C19—H19B | 110.2 |
C23—C22—H22 | 120.6 | H19A—C19—H19B | 108.5 |
C21—C22—H22 | 120.6 | O1—C7—C6 | 123.8 (6) |
C23i—C24—C23 | 117.3 (13) | O1—C7—C2 | 114.9 (4) |
C23i—C24—H24 | 121.4 | C6—C7—C2 | 121.2 (5) |
C23—C24—H24 | 121.4 | C20—N5—C1 | 121.3 (4) |
C10—O2—C9 | 111.9 (4) | C20—N5—P1 | 112.5 (3) |
O2—C10—C11 | 108.5 (5) | C1—N5—P1 | 122.3 (3) |
O2—C10—H10A | 110.0 | C16—C17—C12 | 118.7 (5) |
C11—C10—H10A | 110.0 | C16—C17—C18 | 119.9 (5) |
O2—C10—H10B | 110.0 | C12—C17—C18 | 121.4 (4) |
C11—C10—H10B | 110.0 | P3—N2—P2 | 118.0 (2) |
H10A—C10—H10B | 108.4 | O1—C8—C9 | 106.9 (5) |
O3—C11—C10 | 108.5 (5) | O1—C8—H8A | 110.3 |
O3—C11—H11A | 110.0 | C9—C8—H8A | 110.3 |
C10—C11—H11A | 110.0 | O1—C8—H8B | 110.3 |
O3—C11—H11B | 110.0 | C9—C8—H8B | 110.3 |
C10—C11—H11B | 110.0 | H8A—C8—H8B | 108.6 |
H11A—C11—H11B | 108.4 | C12—C13—C14 | 118.9 (5) |
N3—P1—N4 | 113.1 (2) | C12—C13—H13 | 120.6 |
N3—P1—N1 | 111.60 (19) | C14—C13—H13 | 120.6 |
N4—P1—N1 | 112.1 (2) | C14—C15—C16 | 120.2 (6) |
N3—P1—N5 | 112.2 (2) | C14—C15—H15 | 119.9 |
N4—P1—N5 | 95.43 (18) | C16—C15—H15 | 119.9 |
N1—P1—N5 | 111.5 (2) | N5—C1—C2 | 113.0 (4) |
N3—P3—N2 | 120.3 (2) | N5—C1—H1A | 109.0 |
N3—P3—Cl2 | 109.28 (16) | C2—C1—H1A | 109.0 |
N2—P3—Cl2 | 108.6 (2) | N5—C1—H1B | 109.0 |
N3—P3—Cl1 | 110.00 (18) | C2—C1—H1B | 109.0 |
N2—P3—Cl1 | 107.0 (2) | H1A—C1—H1B | 107.8 |
Cl2—P3—Cl1 | 99.64 (10) | C7—C6—C5 | 118.2 (7) |
N1—P2—N2 | 119.9 (2) | C7—C6—H6 | 120.9 |
N1—P2—Cl4 | 109.94 (17) | C5—C6—H6 | 120.9 |
N2—P2—Cl4 | 108.4 (2) | N5—C20—C19 | 108.5 (4) |
N1—P2—Cl3 | 110.50 (18) | N5—C20—H20A | 110.0 |
N2—P2—Cl3 | 107.6 (2) | C19—C20—H20A | 110.0 |
Cl4—P2—Cl3 | 98.31 (9) | N5—C20—H20B | 110.0 |
C18—N4—C19 | 123.2 (4) | C19—C20—H20B | 110.0 |
C18—N4—P1 | 123.3 (3) | H20A—C20—H20B | 108.4 |
C19—N4—P1 | 113.4 (3) | C4—C3—C2 | 122.1 (7) |
N4—C18—C17 | 113.1 (4) | C4—C3—H3 | 119.0 |
N4—C18—H18A | 109.0 | C2—C3—H3 | 119.0 |
C17—C18—H18A | 109.0 | C15—C14—C13 | 120.9 (5) |
N4—C18—H18B | 109.0 | C15—C14—H14 | 119.6 |
C17—C18—H18B | 109.0 | C13—C14—H14 | 119.6 |
H18A—C18—H18B | 107.8 | C4—C5—C6 | 120.4 (6) |
C12—O3—C11 | 118.1 (4) | C4—C5—H5 | 119.8 |
O3—C12—C13 | 124.3 (5) | C6—C5—H5 | 119.8 |
O3—C12—C17 | 115.1 (4) | O2—C9—C8 | 108.4 (5) |
C13—C12—C17 | 120.6 (5) | O2—C9—H9A | 110.0 |
C7—O1—C8 | 119.3 (4) | C8—C9—H9A | 110.0 |
P2—N1—P1 | 124.7 (2) | O2—C9—H9B | 110.0 |
C3—C2—C7 | 117.7 (5) | C8—C9—H9B | 110.0 |
C3—C2—C1 | 121.5 (6) | H9A—C9—H9B | 108.4 |
C7—C2—C1 | 120.8 (5) | C3—C4—C5 | 120.3 (6) |
P3—N3—P1 | 124.0 (2) | C3—C4—H4 | 119.9 |
C17—C16—C15 | 120.7 (6) | C5—C4—H4 | 119.9 |
| | | |
C24—C23—C22—C21 | 1.6 (12) | N3—P1—N5—C1 | −71.8 (4) |
C22i—C21—C22—C23 | −0.8 (6) | N4—P1—N5—C1 | 170.5 (4) |
C22—C23—C24—C23i | −0.9 (6) | N1—P1—N5—C1 | 54.2 (5) |
C9—O2—C10—C11 | −179.2 (5) | C15—C16—C17—C12 | −0.1 (7) |
O2—C10—C11—O3 | −78.4 (6) | C15—C16—C17—C18 | −180.0 (4) |
N3—P1—N4—C18 | 57.1 (4) | O3—C12—C17—C16 | 179.1 (4) |
N1—P1—N4—C18 | −70.1 (4) | C13—C12—C17—C16 | −0.2 (6) |
N5—P1—N4—C18 | 174.1 (4) | O3—C12—C17—C18 | −1.1 (6) |
N3—P1—N4—C19 | −120.3 (4) | C13—C12—C17—C18 | 179.6 (4) |
N1—P1—N4—C19 | 112.5 (4) | N4—C18—C17—C16 | −113.8 (5) |
N5—P1—N4—C19 | −3.3 (4) | N4—C18—C17—C12 | 66.4 (6) |
C19—N4—C18—C17 | 34.3 (7) | N3—P3—N2—P2 | 9.0 (5) |
P1—N4—C18—C17 | −142.9 (4) | Cl2—P3—N2—P2 | 135.9 (3) |
C10—C11—O3—C12 | 172.8 (4) | Cl1—P3—N2—P2 | −117.4 (3) |
C11—O3—C12—C13 | −3.9 (7) | N1—P2—N2—P3 | −3.8 (5) |
C11—O3—C12—C17 | 176.8 (4) | Cl4—P2—N2—P3 | −131.1 (3) |
N2—P2—N1—P1 | 3.5 (5) | Cl3—P2—N2—P3 | 123.5 (3) |
Cl4—P2—N1—P1 | 130.1 (3) | C7—O1—C8—C9 | −173.0 (5) |
Cl3—P2—N1—P1 | −122.4 (3) | O3—C12—C13—C14 | −179.2 (4) |
N3—P1—N1—P2 | −7.5 (4) | C17—C12—C13—C14 | 0.0 (7) |
N4—P1—N1—P2 | 120.5 (3) | C17—C16—C15—C14 | 0.7 (8) |
N5—P1—N1—P2 | −133.8 (3) | C20—N5—C1—C2 | −46.6 (7) |
N2—P3—N3—P1 | −14.5 (5) | P1—N5—C1—C2 | 157.2 (4) |
Cl2—P3—N3—P1 | −141.1 (3) | C3—C2—C1—N5 | 112.3 (6) |
Cl1—P3—N3—P1 | 110.5 (3) | C7—C2—C1—N5 | −68.5 (6) |
N4—P1—N3—P3 | −114.6 (3) | O1—C7—C6—C5 | 179.1 (5) |
N1—P1—N3—P3 | 12.9 (4) | C2—C7—C6—C5 | 1.1 (8) |
N5—P1—N3—P3 | 138.8 (3) | C1—N5—C20—C19 | −175.8 (5) |
C18—N4—C19—C20 | 176.4 (5) | P1—N5—C20—C19 | −17.4 (6) |
P1—N4—C19—C20 | −6.2 (6) | N4—C19—C20—N5 | 14.3 (7) |
C8—O1—C7—C6 | −2.7 (8) | C7—C2—C3—C4 | 0.3 (9) |
C8—O1—C7—C2 | 175.4 (5) | C1—C2—C3—C4 | 179.5 (5) |
C3—C2—C7—O1 | −178.8 (5) | C16—C15—C14—C13 | −0.9 (8) |
C1—C2—C7—O1 | 2.0 (7) | C12—C13—C14—C15 | 0.6 (7) |
C3—C2—C7—C6 | −0.7 (8) | C7—C6—C5—C4 | −1.3 (9) |
C1—C2—C7—C6 | −179.8 (5) | C10—O2—C9—C8 | −174.4 (5) |
N3—P1—N5—C20 | 130.1 (4) | O1—C8—C9—O2 | 76.9 (6) |
N4—P1—N5—C20 | 12.4 (4) | C2—C3—C4—C5 | −0.5 (10) |
N1—P1—N5—C20 | −103.9 (4) | C6—C5—C4—C3 | 1.0 (10) |
Symmetry code: (i) −x, y, −z+1/2. |