4,4,6,6-Tetra­chloro-1′,3′-[2,2′-(3-oxapentane-1,5-dioxy)­di­benzyl]-2λ⁵,4λ⁵,6λ⁵-cyclo­triphosphazene-2-spiro-2′-1,3,2-di­aza­phospho­lane benzene hemisolvate

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

---

Computing details

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]- 2λ⁵,4λ⁵,6λ⁵-cyclotriphosphazene-2-spiro-2'-1,3,2-diazaphospholane benzene hemisolvate

Crystal data

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) Å^3	0.40 × 0.25 × 0.25 mm
Z = 8

Data collection

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

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)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.197	w = 1/[σ^2(Fo^2) + (0.1326P)^2] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (2)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

C21—C22^i	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—C23^i	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
C22^i—C21—C22	120.5 (10)	C17—C16—H16	119.6
C22^i—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)
C23^i—C24—C23	117.3 (13)	O1—C7—C2	114.9 (4)
C23^i—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)
C22^i—C21—C22—C23	−0.8 (6)	N4—P1—N5—C1	170.5 (4)
C22—C23—C24—C23^i	−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.