Conformational polymorphism in a chiral spiro-cis-ansa-bridged cyclo­triphosphazene derivative

The reaction of spermidine with 2,2,4,4-tetra­chloro-6,6-di­phenyl­cyclo­triphosphazene produces a mixture of products of which one of the fractions is a spiro-cis-ansa deriv­ative, namely 12-chloro-14,14-di­phenyl-2,6,11,13,15,16-hexa­aza-1,12-di­phosphatri­cyclo­[10.3.1.0^1,6]­hexadeca-12,14-diene, C₁₉H₂₆Cl­N₆P₃. Recrystallization of this fraction from different solvents results in the formation of two different crystalline forms. The rod morphology formed in di­chloro­methane-n-hexane (1:1) produces a triclinic structure with three mol­ecules in the asymmetric unit. These three mol­ecules adopt different conformations as a result of two NH groups flipping in an ansa-bridged ring system. The plate morphology crystals, grown in di­chloro­methane-n-hexane-ethyl acetate (1:1:1), produce a C-centred monoclinic structure that adopts a conformation that is essentially the same as one of the forms in the triclinic structure.

S1. Comment

As part of our investigations on the chiral properties of cyclophosphazenes and, in particular, that of configurational isomers, we have investigated the reaction of 2,2,4,4-tetrachloro-6,6-diphenylcyclotriphosphazene with spermine and spermidine. The single-bridged derivatives arising from the reaction with spermine have been demonstrated to be a 50:50 mixture of meso and racemic forms (Coles et al., 2002). The analogous reaction with spermidine is expected to give rise to two racemates, which have been observed by ³¹P NMR, but, so far, have not been separated. Another product from this reaction is a fused tricyclic system (see Scheme below) based on a single trimer unit, which is the subject of the present study as it has given rise to different polymorphic forms.

Polymorphism in cyclophosphazene chemistry has hitherto been confined to tetrameric, N₄P₄, or higher ring systems. A review article (Shaw, 1978) mentions tetrameric and pentameric derivatives. The first and probably the best known are the K– (Hazekamp et al., 1962) and T– (Wagner & Vos, 1968) forms of N₄P₄Cl₈ differing in the shape of the eight-membered N₄P₄ ring. Protonated cationic tetramer species, (N₄HP₄Me₈)₂CoCl₄, display two types of eight-membered-ring conformations in the same unit cell (Trotter & Whitlow, 1970). Three different crystalline modifications of the pentameric fluoride, N₅P₅F₁₀, have been reported, two of which had their structures determined (Hartsuiker & Wagner, 1974; Pauzenga-Hartsuiker, 1975). The acyclic cation (Ph₃P═N-PPh₃)⁺, often favoured to stabilize complex inorganic and organometallic anions, displays a variety of P—N—P bond angles. In one structure, both bent and linear forms have been observed in the same asymmetric unit (Wilson & Bau, 1974).

We now report the first example of polymorphism involving a trimer N₃P₃ structure. Unlike the other examples of polymorphism referred to above, this is not a function of the NP skeleton. The backbone of the structures presented [Figs. 1, 2, 3 and 4 for molecules (Ia), (Ib), (Ic) and (IIa) found in the structures of (I) and (II), respectively] is the cyclic N₃P₃ moiety of cyclotriphosphazene. The driving force behind this polymorphic behaviour is the conformation of two NH groups, which are part of a nine-membered cis-ansa moiety linked to a six-membered bis-amino ring bonded to two P atoms in the N₃P₃ ring. The conformation of the NH moieties is determined by the chiral nature of the P atoms to which they are bonded. An inversion of chirality about these atoms necessitates a flipping of the NH group and as a result there are differing molecular conformations in the two crystal structures presented.

As the conformational arrangements of these molecules are to be compared, their structures will be discussed simultaneously. Selected geometric parameters for the total of four molecules presented are given in Tables 1 and 2 for structures (I) and (II), respectively. The bond lengths and angles in all four molecules conform to expected values derived from structures found in the Cambridge Structural Database (Allen & Kennard, 1993; Orpen et al., 1992). The asymmetric unit of (I) comprises three independent molecules, each exhibiting different conformational forms. Molecules (Ia), (Ib) and (Ic) in (I) are depicted in Figs. 1, 2 and 3, respectively, whilst the structure of (II) [molecule (IIa)] is presented in Fig. 4.

The structures of (I) and (II) exhibit the same connectivity yet crystallize in different space groups, indicating that they are polymorphic in nature. Molecules (Ia), (Ic) and (IIa) all have the same chirality, i.e. R about atoms P2/P3, P8/P9 and P2/P3, whilst molecule (Ib) has S chirality for atoms P5 and P6. The conformations of the primary amino groups, and hence those of the ring systems of which they are components, are best described and compared using the torsion angles given in Tables 1 and 2. The conformation of molecule (Ia) may be assigned as the α form and is described by the torsion angles C13—N4—P2—N1, C16—N5—P2—N1, C16—C17—C18—C19 and C19—N6—P3—N3. Molecule (Ib) has torsion angles (C32—N10—P5—N7, C35—N11—P5—N7, C35—C36—C37—C38 and C38—N12—P6—N9) similar in magnitude but opposite in sign, indicating an inverted conformation to that of the α form, arising from the alternative chirality adopted by P5 and P6. Hence, the R/R racemate generated through the centre of symmetry in the space group would exhibit essentially the same form as that of (Ia), the α form. The β form exhibited by molecule (Ic) [characterized by torsion angles C51—N16—P8—N13, C54—N17—P8—N13, C54—C55—C56—C57 and C57—N18—P9—N15] is similar to that of the α form, apart from the conformation of the N18—P9 bond, which has a torsion angle that is greater than 100° larger in magnitude. Molecule (IIa) has the same numbering scheme as that of molecule (Ia) and is hence characterized by the same torsion angles. Comparison of these angles essentially shows it to be the α form. By puckering analysis (Cremer & Pople, 1975) the conformations of the spiro-P—N—C—C—C—N rings is shown to be that of a boat; however, in the case of molecule (Ib) the apical atoms (P5 and C33) are opposite in orientation to those of the other molecules, which is due to the inversion in chirality about P5. The conformations adopted by the nine-membered rings may be compared using the torsion angles described in Tables 1 and 2 [C16—C17—C18—C19, C35—C36—C37—C38, C54—C55—C56—C57 and C16—C17—C18—C19 for molecules (Ia), (Ib), (Ic) and (IIa) respectively]. From these values, it can be seen that (Ia) and (IIa) adopt a similar α conformation [inverted in (Ib) as a result of the chirality inversion], whereas the conformation is more distorted in (Ic), i.e. the β form.

The behaviour described above has implications on the conformation of the cyclophosphazene ring system, which one would normally expect to be planar. Puckering analysis (Cremer & Pople, 1975) shows the N₃P₃ ring in (Ia) to be a boat, whilst the remaining molecules exhibit a twist-boat conformation. The deviations from planarity are not great, but nevertheless significant [maximum deviations: molecule (Ia) 0.133 Å (P1); (Ib) = 0.259 Å (P4); (Ic) = 0.221 Å (N14); and (IIa) = 0.181 Å (P1)]. The smaller deviations in the α form with respect to that of the β form indicate that less strain on the system is induced by this arrangement. This is not accompanied by a decrease of the P···P non-bonded distance, as has been observed in similar, but shorter, ansa-bridged N₃P₃ systems (Contractor et al., 1986), because the P···P cross-ring separations are comparable to those observed in unstrained N₃P₃ containing structures (Contractor et al., 1986).

S2. Experimental

A solution of 2,2,4,4-tetrachloro-6,6-diphenylcyclotriphosphazene (7.24 g, 0.0168 mol) in a 200 ml mixture of Et₂O and n-hexane (3:5) was added dropwise to a stirred solution of triethylamine (5.10 g, 0.05049 mol) in 200 ml of the same solvent mixture and then spermidine (2.39 g, 0.0168 mol) in 50 ml of the same solvent mixture was added. The reaction mixture was stirred under an atmosphere of argon at room temperature for 22 d. Triethylamine hydrochloride was filtered off and the solvent removed under reduced pressure at 303 K. Two compounds were detected [R_F = 0.9 (product 1) and 0.36 (product 2)] by thin-layer chromatography using dichloromethane–ethyl acetate (3:1) as the mobile phase. These were separated by column chromatography on silica gel using dichloromethane–ethyl acetate (1:1) as eluent. The isomeric mixture of the singly bridged compound (product 1) was obtained as a colourless solid (m.p. 331–341 K, 2.5 g, yield 13.23%) and the fused tricyclic derivative (product 2), the title compound, was initially crystallized from dichloromethane–n-hexane (1:1) (m.p. 449 K, 0.8 g, yield 10%) to give structure (I) and then from DCM–ethyl acetate–n-hexane (1:1:1) to give structure (II). Found (product 2): C 48.8, H 5.10, N 18.00%; M⁺ 467.1. C₁₉H₂₆ClN₆P₃ requires: C 48.89, H 5.61, N 18.00%; M 466.8.

S3. Refinement

For both structures, the amino H atoms were found experimentally from a difference map and freely refined, whilst the remaining H atoms were located in idealized positions (C—H = 0.95 and 0.99 Å) with their displacement parameters riding on those of the parent atom. The ansa-bridged ring in molecules (Ia) and (Ib) exhibit positional disorder about atoms C17 and C36 (50 and 75% site occupation, respectively). Both components were constrained to idealized methylene bond lengths with isotropic displacement parameters.

Computing details

For both compounds, cell refinement: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); data reduction: COLLECT and DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

Figures

	Fig. 1. View of molecule (Ia) in the structure of (I), shown with 50% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.
	Fig. 2. View of molecule (Ib) in the structure of (I, shown with 50% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.
	Fig. 3. View of molecule (Ic) in the structure of (I), shown with 50% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.
	Fig. 4. View of the molecular structure of (II), molecule (IIa), shown with 50% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.

(I)

Crystal data

C19H26ClN6P3	Z = 2
Mr = 466.82	F(000) = 1464
Triclinic, P1	Dx = 1.418 Mg m^−3
a = 10.083 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.770 (3) Å	Cell parameters from 21067 reflections
c = 25.816 (5) Å	θ = 2.9–27.5°
α = 95.64 (3)°	µ = 0.41 mm^−1
β = 96.98 (3)°	T = 120 K
γ = 92.07 (3)°	Rod, colourless
V = 3279.5 (11) Å^3	0.18 × 0.08 × 0.05 mm

Data collection

Nonius KappaCCD area-detector diffractometer	8616 reflections with I > 2σ(I)
ϕ and ω scans	Rint = 0.071
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	θmax = 27.5°, θmin = 2.9°
Tmin = 0.929, Tmax = 0.980	h = −13→13
42350 measured reflections	k = −16→16
14040 independent reflections	l = −33→33

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0724P)^2 + 0.3311P] where P = (Fo^2 + 2Fc^2)/3
14040 reflections	(Δ/σ)max = 0.081
807 parameters	Δρmax = 1.28 e Å^−3
12 restraints	Δρmin = −1.25 e Å^−3

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	1.3424 (3)	0.6147 (2)	0.90941 (11)	0.0396 (8)
C2	1.3999 (3)	0.6441 (3)	0.86725 (12)	0.0548 (10)
H2	1.3681	0.7020	0.8497	0.066*
C3	1.5081 (3)	0.5865 (3)	0.85005 (14)	0.0761 (13)
H3	1.5495	0.6062	0.8211	0.091*
C4	1.5520 (3)	0.5023 (3)	0.87571 (16)	0.0748 (13)
H4	1.6236	0.4640	0.8639	0.090*
C5	1.4949 (3)	0.4723 (3)	0.91780 (17)	0.0723 (13)
H5	1.5265	0.4143	0.9353	0.087*
C6	1.3909 (3)	0.5282 (2)	0.93407 (15)	0.0564 (10)
H6	1.3504	0.5074	0.9631	0.068*
C7	1.2830 (3)	0.76093 (19)	0.99355 (10)	0.0296 (7)
C8	1.3830 (3)	0.8367 (2)	0.99093 (11)	0.0437 (8)
H8	1.4108	0.8483	0.9580	0.052*
C9	1.4429 (3)	0.8959 (2)	1.03636 (12)	0.0506 (9)
H9	1.5112	0.9480	1.0344	0.061*
C10	1.4031 (3)	0.8791 (2)	1.08420 (12)	0.0460 (9)
H10	1.4447	0.9190	1.1153	0.055*
C11	1.3041 (3)	0.8054 (2)	1.08693 (12)	0.0496 (9)
H11	1.2767	0.7940	1.1199	0.059*
C12	1.2431 (3)	0.7467 (2)	1.04169 (11)	0.0439 (8)
H12	1.1731	0.6961	1.0439	0.053*
C13	0.8806 (3)	0.7606 (2)	0.76703 (11)	0.0388 (8)
H13A	0.8123	0.7040	0.7692	0.047*
H13B	0.8975	0.7594	0.7300	0.047*
C14	0.8289 (3)	0.8662 (2)	0.78491 (12)	0.0455 (9)
H14A	0.7503	0.8811	0.7603	0.055*
H14B	0.8991	0.9222	0.7845	0.055*
C15	0.7896 (3)	0.8672 (2)	0.83981 (12)	0.0462 (9)
H15A	0.7619	0.9385	0.8512	0.055*
H15B	0.7117	0.8173	0.8390	0.055*
C16	0.86495 (8)	0.85055 (14)	0.93217 (6)	0.0599 (10)
H16A	0.8902	0.9259	0.9430	0.072*
H16B	0.9363	0.8120	0.9508	0.072*
C17	0.74701 (15)	0.83228 (7)	0.96402 (8)	0.0220 (8)	0.237 (5)
H17A	0.6647	0.8562	0.9446	0.026*	0.237 (5)
H17B	0.7646	0.8771	0.9979	0.026*	0.237 (5)
C17'	0.73092 (13)	0.78585 (11)	0.92995 (5)	0.112 (2)	0.763 (5)
H17C	0.6575	0.8353	0.9294	0.134*	0.763 (5)
H17D	0.7167	0.7394	0.8965	0.134*	0.763 (5)
C18	0.7202 (3)	0.71702 (9)	0.97548 (7)	0.115 (2)
H18A	0.6588	0.7193	1.0027	0.138*
H18B	0.6702	0.6796	0.9432	0.138*
C19	0.8269 (3)	0.6520 (2)	0.99208 (12)	0.0455 (8)
H19A	0.8121	0.6310	1.0269	0.055*
H19B	0.9111	0.6962	0.9971	0.055*
N1	1.1418 (2)	0.76046 (16)	0.89453 (8)	0.0317 (6)
N2	0.9215 (2)	0.62939 (15)	0.87237 (8)	0.0283 (5)
N3	1.1067 (2)	0.59708 (16)	0.95304 (8)	0.0330 (6)
N4	1.0061 (2)	0.74142 (16)	0.80033 (8)	0.0306 (6)
N5	0.8988 (2)	0.83828 (16)	0.87846 (9)	0.0348 (6)
N6	0.8481 (2)	0.55598 (16)	0.95856 (8)	0.0312 (6)
P1	1.20643 (7)	0.68303 (5)	0.93471 (3)	0.02953 (18)
P2	0.99490 (7)	0.73846 (5)	0.86324 (3)	0.02848 (17)
P3	0.96450 (7)	0.56492 (5)	0.91961 (3)	0.02814 (17)
Cl1	0.96498 (7)	0.41079 (5)	0.88954 (3)	0.03920 (19)
C20	0.3384 (2)	0.63716 (17)	0.35175 (9)	0.0214 (6)
C21	0.2720 (2)	0.54289 (18)	0.35884 (10)	0.0275 (7)
H21	0.2895	0.5129	0.3911	0.033*
C22	0.1800 (3)	0.49276 (19)	0.31860 (11)	0.0313 (7)
H22	0.1344	0.4291	0.3239	0.038*
C23	0.1541 (3)	0.5337 (2)	0.27148 (11)	0.0357 (8)
H23	0.0929	0.4980	0.2440	0.043*
C24	0.2192 (3)	0.6287 (2)	0.26451 (11)	0.0383 (8)
H24	0.2015	0.6584	0.2322	0.046*
C25	0.3094 (3)	0.6799 (2)	0.30451 (10)	0.0321 (7)
H25	0.3521	0.7451	0.2996	0.039*
C26	0.4031 (2)	0.82634 (17)	0.42496 (9)	0.0186 (6)
C27	0.3411 (2)	0.83565 (19)	0.47068 (9)	0.0249 (6)
H27	0.3232	0.7747	0.4875	0.030*
C28	0.3056 (2)	0.93363 (19)	0.49158 (10)	0.0291 (7)
H28	0.2630	0.9393	0.5225	0.035*
C29	0.3319 (2)	1.02262 (19)	0.46767 (10)	0.0294 (7)
H29	0.3090	1.0896	0.4824	0.035*
C30	0.3918 (3)	1.01403 (19)	0.42211 (11)	0.0313 (7)
H30	0.4083	1.0751	0.4052	0.038*
C31	0.4277 (2)	0.91697 (18)	0.40117 (10)	0.0270 (6)
H31	0.4698	0.9121	0.3701	0.032*
C32	0.9282 (2)	0.8979 (2)	0.42656 (10)	0.0322 (7)
H32A	0.9584	0.8772	0.4619	0.039*
H32B	0.9450	0.9750	0.4275	0.039*
C33	1.0076 (3)	0.8416 (2)	0.38679 (11)	0.0366 (8)
H33A	0.9774	0.8627	0.3515	0.044*
H33B	1.1035	0.8636	0.3957	0.044*
C34	0.9914 (3)	0.7229 (2)	0.38533 (11)	0.0362 (7)
H34A	1.0397	0.6898	0.3573	0.043*
H34B	1.0324	0.7011	0.4192	0.043*
C35	0.83072 (18)	0.57042 (18)	0.35966 (6)	0.0413 (7)*
H35A	0.8536	0.5598	0.3233	0.050*
H35B	0.7334	0.5538	0.3573	0.050*
C36	0.8965 (3)	0.4874 (3)	0.38765 (13)	0.0336 (9)*	0.766 (4)
H36A	0.8686	0.4183	0.3676	0.040*	0.766 (4)
H36B	0.9944	0.4976	0.3879	0.040*	0.766 (4)
C36'	0.9129 (4)	0.5507 (5)	0.41458 (10)	0.035 (3)*	0.234 (4)
H36C	1.0031	0.5298	0.4075	0.042*	0.234 (4)
H36D	0.9249	0.6193	0.4365	0.042*	0.234 (4)
C37	0.8680 (3)	0.4834 (3)	0.44247 (13)	0.0536 (8)*
H37A	0.8951	0.5527	0.4623	0.064*
H37B	0.9247	0.4304	0.4585	0.064*
C38	0.7215 (2)	0.45638 (19)	0.44933 (10)	0.0298 (7)
H38A	0.6621	0.4699	0.4175	0.036*
H38B	0.7103	0.3808	0.4543	0.036*
N7	0.59369 (18)	0.72563 (14)	0.37250 (7)	0.0194 (5)
N8	0.73921 (19)	0.71003 (14)	0.46598 (7)	0.0203 (5)
N9	0.48550 (19)	0.62735 (14)	0.44824 (7)	0.0202 (5)
N10	0.78406 (17)	0.87171 (10)	0.41318 (5)	0.0237 (5)
N11	0.84986 (19)	0.68468 (15)	0.37572 (8)	0.0252 (5)
N12	0.6847 (2)	0.52100 (15)	0.49506 (8)	0.0261 (5)
P4	0.46370 (6)	0.70183 (4)	0.40109 (2)	0.01903 (15)
P5	0.73643 (6)	0.74502 (5)	0.40754 (2)	0.02041 (15)
P6	0.62769 (6)	0.63663 (5)	0.48377 (2)	0.02108 (15)
Cl2	0.59698 (6)	0.69072 (5)	0.55835 (2)	0.02968 (16)
C39	0.1471 (2)	−0.12569 (18)	0.66002 (10)	0.0260 (6)
C40	0.0129 (3)	−0.1088 (2)	0.66526 (11)	0.0394 (8)
H40	−0.0115	−0.0757	0.6971	0.047*
C41	−0.0842 (3)	−0.1412 (3)	0.62327 (12)	0.0507 (9)
H41	−0.1756	−0.1312	0.6270	0.061*
C42	−0.0510 (3)	−0.1877 (2)	0.57633 (11)	0.0438 (8)
H42	−0.1187	−0.2103	0.5482	0.053*
C43	0.0821 (3)	−0.2009 (2)	0.57088 (11)	0.0384 (8)
H43	0.1061	−0.2317	0.5385	0.046*
C44	0.1801 (3)	−0.1699 (2)	0.61193 (10)	0.0317 (7)
H44	0.2714	−0.1786	0.6075	0.038*
C45	0.3659 (2)	−0.21159 (19)	0.71504 (10)	0.0266 (7)
C46	0.3083 (3)	−0.3023 (2)	0.73031 (11)	0.0381 (8)
H46	0.2234	−0.3004	0.7426	0.046*
C47	0.3746 (3)	−0.3957 (2)	0.72758 (13)	0.0509 (9)
H47	0.3362	−0.4575	0.7385	0.061*
C48	0.4979 (3)	−0.3978 (2)	0.70865 (12)	0.0487 (9)
H48	0.5432	−0.4617	0.7065	0.058*
C49	0.5541 (3)	−0.3103 (2)	0.69337 (11)	0.0386 (8)
H49	0.6384	−0.3129	0.6805	0.046*
C50	0.4887 (3)	−0.2168 (2)	0.69652 (10)	0.0333 (7)
H50	0.5288	−0.1554	0.6858	0.040*
C51	0.2031 (3)	0.0428 (2)	0.91327 (11)	0.0425 (8)
H51A	0.2675	0.1042	0.9215	0.051*
H51B	0.2069	0.0034	0.9446	0.051*
C52	0.0639 (3)	0.0804 (2)	0.90072 (11)	0.0458 (9)
H52A	0.0001	0.0188	0.8913	0.055*
H52B	0.0378	0.1212	0.9322	0.055*
C53	0.0556 (3)	0.1480 (2)	0.85625 (11)	0.0428 (8)
H53A	−0.0396	0.1602	0.8453	0.051*
H53B	0.1014	0.2173	0.8690	0.051*
C54	0.0937 (3)	0.16376 (19)	0.76459 (10)	0.0315 (7)
H54A	−0.0030	0.1587	0.7514	0.038*
H54B	0.1413	0.1296	0.7366	0.038*
C55	0.1397 (3)	0.2811 (2)	0.77375 (11)	0.0361 (7)
H55A	0.1332	0.3093	0.7392	0.043*
H55B	0.0757	0.3186	0.7942	0.043*
C56	0.2800 (3)	0.3086 (2)	0.80177 (11)	0.0353 (7)
H56A	0.2818	0.3811	0.8195	0.042*
H56B	0.2985	0.2605	0.8293	0.042*
C57	0.3922 (3)	0.30256 (19)	0.76739 (11)	0.0338 (7)
H57A	0.3883	0.3632	0.7462	0.041*
H57B	0.4790	0.3091	0.7903	0.041*
N13	0.1992 (2)	−0.07999 (15)	0.76704 (8)	0.0267 (5)
N14	0.3746 (2)	0.07920 (14)	0.80620 (8)	0.0257 (5)
N15	0.3685 (2)	0.00306 (15)	0.70382 (8)	0.0285 (6)
N16	0.2407 (2)	−0.02515 (16)	0.86913 (8)	0.0332 (6)
N17	0.1146 (2)	0.10323 (16)	0.81053 (8)	0.0296 (6)
N18	0.3875 (2)	0.20524 (15)	0.73198 (8)	0.0256 (5)
P7	0.27298 (6)	−0.09339 (5)	0.71551 (2)	0.02276 (16)
P8	0.23538 (7)	0.01850 (5)	0.81155 (3)	0.02572 (17)
P9	0.41908 (7)	0.09054 (5)	0.75073 (3)	0.02404 (16)
Cl3	0.62644 (6)	0.08788 (5)	0.76304 (3)	0.03483 (17)
H4N	1.067 (2)	0.7835 (19)	0.7946 (10)	0.036 (8)*
H6N	0.849 (3)	0.499 (2)	0.9769 (11)	0.053 (9)*
H10N	0.7485 (5)	0.9093 (3)	0.38460 (12)	0.018*
H12N	0.645 (3)	0.498 (2)	0.5130 (11)	0.042 (9)*
H16N	0.209 (2)	−0.0844 (18)	0.8667 (9)	0.024 (7)*
H18N	0.404 (2)	0.2118 (18)	0.7047 (9)	0.023 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0267 (14)	0.0500 (17)	0.0363 (17)	0.0033 (13)	−0.0038 (13)	−0.0143 (14)
C2	0.0345 (16)	0.088 (2)	0.0379 (18)	0.0005 (17)	0.0046 (15)	−0.0098 (17)
C3	0.0407 (19)	0.130 (3)	0.049 (2)	−0.002 (2)	0.0063 (17)	−0.030 (2)
C4	0.0378 (19)	0.092 (3)	0.080 (3)	0.0161 (19)	−0.0093 (19)	−0.048 (2)
C5	0.043 (2)	0.071 (2)	0.094 (3)	0.0173 (18)	−0.008 (2)	−0.024 (2)
C6	0.0367 (17)	0.0513 (19)	0.075 (2)	0.0089 (16)	−0.0022 (17)	−0.0131 (18)
C7	0.0313 (14)	0.0284 (13)	0.0291 (14)	0.0037 (12)	0.0017 (12)	0.0046 (11)
C8	0.0457 (17)	0.0519 (17)	0.0310 (16)	−0.0099 (15)	−0.0010 (14)	0.0036 (14)
C9	0.0503 (18)	0.0532 (18)	0.0428 (19)	−0.0163 (16)	−0.0036 (16)	−0.0039 (15)
C10	0.0484 (18)	0.0512 (18)	0.0333 (17)	0.0017 (15)	−0.0048 (15)	−0.0090 (14)
C11	0.0580 (19)	0.0622 (19)	0.0279 (16)	−0.0028 (17)	0.0062 (15)	0.0027 (15)
C12	0.0507 (18)	0.0473 (17)	0.0318 (16)	−0.0062 (15)	0.0041 (14)	−0.0011 (14)
C13	0.0464 (17)	0.0337 (14)	0.0330 (16)	0.0046 (13)	−0.0111 (14)	0.0053 (12)
C14	0.0484 (18)	0.0389 (15)	0.0448 (18)	0.0160 (14)	−0.0135 (15)	0.0014 (14)
C15	0.0395 (17)	0.0330 (14)	0.065 (2)	0.0150 (13)	−0.0010 (16)	0.0054 (15)
C16	0.077 (2)	0.0565 (19)	0.055 (2)	0.0282 (18)	0.0288 (18)	0.0170 (16)
C17	0.0226 (10)	0.0220 (10)	0.0214 (11)	0.0013 (7)	0.0030 (7)	0.0020 (7)
C17'	0.039 (2)	0.244 (7)	0.073 (3)	0.060 (3)	0.034 (2)	0.069 (4)
C18	0.036 (2)	0.051 (2)	0.253 (7)	0.0062 (18)	0.006 (3)	0.002 (3)
C19	0.0503 (17)	0.0328 (15)	0.0554 (19)	−0.0014 (14)	0.0250 (15)	−0.0064 (14)
N1	0.0310 (12)	0.0356 (11)	0.0282 (12)	−0.0046 (10)	0.0012 (10)	0.0072 (10)
N2	0.0280 (11)	0.0281 (11)	0.0289 (12)	0.0017 (9)	0.0026 (10)	0.0038 (9)
N3	0.0346 (12)	0.0316 (11)	0.0327 (12)	0.0045 (10)	−0.0008 (10)	0.0086 (10)
N4	0.0335 (12)	0.0304 (11)	0.0283 (12)	0.0043 (10)	0.0023 (10)	0.0052 (10)
N5	0.0404 (13)	0.0294 (11)	0.0349 (13)	0.0086 (10)	0.0060 (11)	0.0003 (10)
N6	0.0359 (12)	0.0290 (11)	0.0294 (12)	0.0009 (10)	0.0074 (10)	0.0029 (10)
P1	0.0281 (4)	0.0337 (4)	0.0263 (4)	0.0029 (3)	0.0009 (3)	0.0032 (3)
P2	0.0283 (4)	0.0287 (3)	0.0281 (4)	0.0032 (3)	0.0013 (3)	0.0036 (3)
P3	0.0296 (4)	0.0277 (3)	0.0272 (4)	0.0042 (3)	0.0033 (3)	0.0026 (3)
Cl1	0.0555 (4)	0.0263 (3)	0.0369 (4)	0.0042 (3)	0.0117 (3)	0.0005 (3)
C20	0.0177 (11)	0.0229 (12)	0.0221 (13)	0.0068 (10)	0.0005 (10)	−0.0042 (10)
C21	0.0296 (13)	0.0248 (12)	0.0274 (14)	0.0044 (11)	0.0030 (11)	−0.0006 (11)
C22	0.0315 (14)	0.0202 (12)	0.0395 (16)	0.0023 (11)	0.0006 (13)	−0.0065 (12)
C23	0.0271 (14)	0.0397 (15)	0.0355 (16)	0.0066 (12)	−0.0051 (13)	−0.0108 (13)
C24	0.0330 (15)	0.0512 (16)	0.0304 (15)	0.0044 (14)	−0.0023 (13)	0.0097 (13)
C25	0.0284 (14)	0.0353 (14)	0.0313 (15)	−0.0050 (12)	−0.0004 (12)	0.0040 (12)
C26	0.0161 (11)	0.0194 (11)	0.0194 (12)	0.0037 (10)	−0.0002 (10)	−0.0012 (10)
C27	0.0252 (13)	0.0258 (12)	0.0242 (13)	0.0015 (11)	0.0048 (11)	0.0030 (10)
C28	0.0300 (14)	0.0355 (14)	0.0217 (13)	0.0080 (12)	0.0052 (11)	−0.0026 (11)
C29	0.0273 (13)	0.0243 (12)	0.0344 (15)	0.0071 (11)	0.0015 (12)	−0.0075 (11)
C30	0.0336 (14)	0.0216 (12)	0.0395 (16)	0.0043 (12)	0.0061 (13)	0.0045 (11)
C31	0.0292 (13)	0.0258 (12)	0.0274 (14)	0.0077 (11)	0.0070 (11)	0.0023 (11)
C32	0.0273 (13)	0.0382 (14)	0.0290 (15)	−0.0093 (12)	−0.0024 (12)	0.0035 (12)
C33	0.0195 (13)	0.0610 (18)	0.0278 (15)	−0.0037 (13)	0.0010 (12)	0.0024 (13)
C34	0.0240 (13)	0.0514 (17)	0.0332 (16)	0.0121 (13)	0.0033 (12)	0.0011 (13)
C38	0.0329 (14)	0.0238 (12)	0.0355 (15)	0.0042 (11)	0.0098 (12)	0.0098 (11)
N7	0.0180 (9)	0.0202 (9)	0.0203 (10)	0.0052 (8)	0.0035 (8)	0.0003 (8)
N8	0.0219 (10)	0.0198 (9)	0.0179 (10)	0.0009 (8)	−0.0005 (8)	−0.0007 (8)
N9	0.0210 (10)	0.0182 (9)	0.0214 (10)	0.0014 (8)	0.0022 (8)	0.0028 (8)
N10	0.0231 (10)	0.0221 (10)	0.0260 (11)	0.0008 (9)	0.0033 (9)	0.0033 (9)
N11	0.0210 (10)	0.0285 (11)	0.0264 (11)	0.0074 (9)	0.0043 (9)	0.0010 (9)
N12	0.0290 (11)	0.0227 (10)	0.0265 (11)	−0.0005 (9)	0.0004 (10)	0.0061 (9)
P4	0.0189 (3)	0.0178 (3)	0.0203 (3)	0.0031 (3)	0.0025 (3)	0.0007 (2)
P5	0.0198 (3)	0.0222 (3)	0.0192 (3)	0.0035 (3)	0.0024 (3)	0.0013 (3)
P6	0.0250 (3)	0.0179 (3)	0.0196 (3)	0.0005 (3)	0.0003 (3)	0.0015 (2)
Cl2	0.0392 (3)	0.0290 (3)	0.0205 (3)	−0.0045 (3)	0.0055 (3)	0.0011 (3)
C39	0.0275 (13)	0.0255 (12)	0.0243 (13)	0.0025 (11)	−0.0015 (11)	0.0036 (11)
C40	0.0329 (15)	0.0549 (17)	0.0317 (15)	0.0071 (14)	0.0037 (13)	0.0097 (13)
C41	0.0287 (15)	0.086 (2)	0.0382 (17)	−0.0025 (16)	−0.0023 (14)	0.0210 (16)
C42	0.0412 (17)	0.0600 (18)	0.0265 (15)	−0.0114 (15)	−0.0106 (13)	0.0088 (14)
C43	0.0459 (17)	0.0446 (16)	0.0220 (14)	0.0013 (14)	−0.0024 (13)	−0.0019 (12)
C44	0.0302 (14)	0.0362 (14)	0.0279 (15)	0.0062 (12)	0.0023 (12)	−0.0014 (12)
C45	0.0294 (13)	0.0280 (13)	0.0209 (13)	0.0071 (11)	−0.0009 (11)	−0.0025 (11)
C46	0.0450 (16)	0.0283 (14)	0.0427 (17)	0.0100 (13)	0.0113 (14)	0.0017 (12)
C47	0.072 (2)	0.0278 (14)	0.058 (2)	0.0134 (15)	0.0222 (17)	0.0096 (14)
C48	0.0621 (19)	0.0434 (16)	0.0424 (18)	0.0300 (15)	0.0098 (16)	0.0001 (14)
C49	0.0407 (16)	0.0453 (16)	0.0304 (15)	0.0169 (14)	0.0039 (13)	0.0019 (13)
C50	0.0332 (15)	0.0395 (15)	0.0258 (14)	0.0026 (13)	−0.0014 (12)	0.0023 (12)
C51	0.067 (2)	0.0334 (15)	0.0276 (15)	−0.0011 (15)	0.0143 (14)	−0.0026 (12)
C52	0.0596 (19)	0.0429 (16)	0.0355 (17)	0.0012 (15)	0.0199 (15)	−0.0102 (14)
C53	0.0496 (17)	0.0421 (16)	0.0402 (17)	0.0157 (14)	0.0195 (14)	0.0006 (13)
C54	0.0334 (14)	0.0327 (14)	0.0281 (15)	0.0142 (12)	0.0023 (12)	−0.0012 (12)
C55	0.0418 (16)	0.0306 (14)	0.0385 (16)	0.0126 (13)	0.0098 (13)	0.0064 (12)
C56	0.0465 (16)	0.0224 (13)	0.0355 (16)	0.0048 (13)	0.0032 (14)	−0.0040 (12)
C57	0.0418 (15)	0.0230 (13)	0.0363 (16)	0.0012 (12)	0.0073 (13)	−0.0012 (12)
N13	0.0297 (11)	0.0241 (10)	0.0259 (11)	−0.0021 (9)	0.0034 (9)	0.0015 (9)
N14	0.0340 (11)	0.0200 (10)	0.0228 (11)	0.0006 (9)	0.0018 (9)	0.0035 (8)
N15	0.0368 (12)	0.0236 (10)	0.0247 (11)	−0.0036 (10)	0.0073 (10)	−0.0014 (9)
N16	0.0526 (14)	0.0227 (11)	0.0252 (12)	−0.0026 (11)	0.0092 (11)	0.0021 (9)
N17	0.0353 (12)	0.0297 (11)	0.0239 (11)	0.0085 (10)	0.0055 (10)	−0.0011 (9)
N18	0.0331 (12)	0.0225 (10)	0.0221 (11)	0.0041 (9)	0.0042 (10)	0.0043 (9)
P7	0.0271 (3)	0.0197 (3)	0.0205 (3)	0.0019 (3)	0.0015 (3)	−0.0013 (3)
P8	0.0321 (4)	0.0235 (3)	0.0210 (3)	0.0010 (3)	0.0039 (3)	−0.0005 (3)
P9	0.0268 (3)	0.0222 (3)	0.0224 (3)	0.0027 (3)	0.0001 (3)	0.0015 (3)
Cl3	0.0284 (3)	0.0375 (3)	0.0393 (4)	0.0055 (3)	0.0007 (3)	0.0109 (3)

Geometric parameters (Å, º)

C1—C2	1.371 (4)	C33—H33B	0.9900
C1—C6	1.402 (4)	C34—N11	1.475 (3)
C1—P1	1.806 (3)	C34—H34A	0.9900
C2—C3	1.428 (5)	C34—H34B	0.9900
C2—H2	0.9500	C35—N11	1.476 (3)
C3—C4	1.376 (6)	C35—C36	1.474 (4)
C3—H3	0.9500	C35—C36'	1.6000 (11)
C4—C5	1.369 (6)	C35—H35A	0.9900
C4—H4	0.9500	C35—H35B	0.9900
C5—C6	1.373 (5)	C36—C37	1.483 (5)
C5—H5	0.9500	C36—H36A	0.9900
C6—H6	0.9500	C36—H36B	0.9900
C7—C12	1.379 (4)	C36'—C37	1.279 (6)
C7—C8	1.384 (4)	C36'—H36C	0.9900
C7—P1	1.804 (3)	C36'—H36D	0.9900
C8—C9	1.390 (4)	C37—C38	1.540 (4)
C8—H8	0.9500	C37—H37A	0.9900
C9—C10	1.378 (4)	C37—H37B	0.9900
C9—H9	0.9500	C38—N12	1.466 (3)
C10—C11	1.360 (4)	C38—H38A	0.9900
C10—H10	0.9500	C38—H38B	0.9900
C11—C12	1.387 (4)	N7—P5	1.601 (2)
C11—H11	0.9500	N7—P4	1.614 (2)
C12—H12	0.9500	N8—P6	1.577 (2)
C13—N4	1.483 (3)	N8—P5	1.612 (2)
C13—C14	1.513 (4)	N9—P6	1.599 (2)
C13—H13A	0.9900	N9—P4	1.616 (2)
C13—H13B	0.9900	N10—P5	1.6582 (15)
C14—C15	1.516 (4)	N10—H10N	0.9597 (10)
C14—H14A	0.9900	N11—P5	1.657 (2)
C14—H14B	0.9900	N12—P6	1.643 (2)
C15—N5	1.476 (4)	N12—H12N	0.73 (3)
C15—H15A	0.9900	P6—Cl2	2.0440 (10)
C15—H15B	0.9900	C39—C44	1.395 (4)
C16—N5	1.463 (3)	C39—C40	1.399 (4)
C16—C17	1.5492 (10)	C39—P7	1.799 (2)
C16—C17'	1.5503 (10)	C40—C41	1.389 (4)
C16—H16A	0.9900	C40—H40	0.9500
C16—H16B	0.9900	C41—C42	1.380 (4)
C17—C18	1.5501 (10)	C41—H41	0.9500
C17—H17A	0.9900	C42—C43	1.380 (4)
C17—H17B	0.9900	C42—H42	0.9500
C17'—C18	1.5467 (10)	C43—C44	1.376 (4)
C17'—H17C	0.9900	C43—H43	0.9500
C17'—H17D	0.9900	C44—H44	0.9500
C18—C19	1.433 (4)	C45—C50	1.382 (4)
C18—H18A	0.9900	C45—C46	1.390 (4)
C18—H18B	0.9900	C45—P7	1.805 (3)
C19—N6	1.467 (3)	C46—C47	1.388 (4)
C19—H19A	0.9900	C46—H46	0.9500
C19—H19B	0.9900	C47—C48	1.390 (4)
N1—P2	1.600 (2)	C47—H47	0.9500
N1—P1	1.601 (2)	C48—C49	1.349 (4)
N2—P3	1.565 (2)	C48—H48	0.9500
N2—P2	1.605 (2)	C49—C50	1.385 (4)
N3—P3	1.599 (2)	C49—H49	0.9500
N3—P1	1.606 (2)	C50—H50	0.9500
N4—P2	1.646 (2)	C51—N16	1.459 (3)
N4—H4N	0.84 (2)	C51—C52	1.509 (4)
N5—P2	1.674 (2)	C51—H51A	0.9900
N6—P3	1.644 (2)	C51—H51B	0.9900
N6—H6N	0.91 (3)	C52—C53	1.499 (4)
P3—Cl1	2.0439 (11)	C52—H52A	0.9900
C20—C25	1.388 (4)	C52—H52B	0.9900
C20—C21	1.395 (3)	C53—N17	1.462 (3)
C20—P4	1.797 (2)	C53—H53A	0.9900
C21—C22	1.393 (3)	C53—H53B	0.9900
C21—H21	0.9500	C54—N17	1.476 (3)
C22—C23	1.371 (4)	C54—C55	1.540 (3)
C22—H22	0.9500	C54—H54A	0.9900
C23—C24	1.396 (4)	C54—H54B	0.9900
C23—H23	0.9500	C55—C56	1.521 (4)
C24—C25	1.385 (4)	C55—H55A	0.9900
C24—H24	0.9500	C55—H55B	0.9900
C25—H25	0.9500	C56—C57	1.521 (4)
C26—C31	1.391 (3)	C56—H56A	0.9900
C26—C27	1.398 (3)	C56—H56B	0.9900
C26—P4	1.803 (2)	C57—N18	1.464 (3)
C27—C28	1.390 (3)	C57—H57A	0.9900
C27—H27	0.9500	C57—H57B	0.9900
C28—C29	1.378 (4)	N13—P7	1.599 (2)
C28—H28	0.9500	N13—P8	1.617 (2)
C29—C30	1.383 (4)	N14—P9	1.570 (2)
C29—H29	0.9500	N14—P8	1.606 (2)
C30—C31	1.381 (3)	N15—P9	1.587 (2)
C30—H30	0.9500	N15—P7	1.611 (2)
C31—H31	0.9500	N16—P8	1.634 (2)
C32—N10	1.471 (3)	N16—H16N	0.80 (2)
C32—C33	1.519 (4)	N17—P8	1.657 (2)
C32—H32A	0.9900	N18—P9	1.618 (2)
C32—H32B	0.9900	N18—H18N	0.76 (2)
C33—C34	1.514 (4)	P9—Cl3	2.0783 (10)
C33—H33A	0.9900
C2—C1—C6	118.9 (3)	N11—C35—C36	125.34 (18)
C2—C1—P1	122.6 (2)	N11—C35—C36'	88.3 (3)
C6—C1—P1	118.4 (2)	C36—C35—C36'	38.0 (3)
C1—C2—C3	119.1 (3)	N11—C35—H35A	106.1
C1—C2—H2	120.4	C36—C35—H35A	105.9
C3—C2—H2	120.4	C36'—C35—H35A	131.4
C4—C3—C2	119.6 (4)	N11—C35—H35B	106.1
C4—C3—H3	120.2	C36—C35—H35B	105.9
C2—C3—H3	120.2	C36'—C35—H35B	114.0
C5—C4—C3	121.6 (4)	H35A—C35—H35B	106.3
C5—C4—H4	119.2	C37—C36—C35	115.4 (3)
C3—C4—H4	119.2	C37—C36—H36A	108.4
C4—C5—C6	118.4 (4)	C35—C36—H36A	108.6
C4—C5—H5	120.8	C37—C36—H36B	108.4
C6—C5—H5	120.8	C35—C36—H36B	108.3
C5—C6—C1	122.4 (4)	H36A—C36—H36B	107.5
C5—C6—H6	118.8	C37—C36'—C35	120.1 (4)
C1—C6—H6	118.8	C37—C36'—H36C	107.6
C12—C7—C8	118.9 (2)	C35—C36'—H36C	107.6
C12—C7—P1	120.9 (2)	C37—C36'—H36D	106.9
C8—C7—P1	120.2 (2)	C35—C36'—H36D	106.9
C7—C8—C9	120.2 (3)	H36C—C36'—H36D	107.0
C7—C8—H8	119.9	C36'—C37—C36	42.0 (3)
C9—C8—H8	119.9	C36'—C37—C38	128.2 (3)
C10—C9—C8	120.0 (3)	C36—C37—C38	115.8 (3)
C10—C9—H9	120.0	C36'—C37—H37A	66.4
C8—C9—H9	120.0	C36—C37—H37A	108.4
C11—C10—C9	120.0 (3)	C38—C37—H37A	108.3
C11—C10—H10	120.0	C36'—C37—H37B	122.6
C9—C10—H10	120.0	C36—C37—H37B	108.3
C10—C11—C12	120.3 (3)	C38—C37—H37B	108.3
C10—C11—H11	119.9	H37A—C37—H37B	107.4
C12—C11—H11	119.9	N12—C38—C37	109.6 (2)
C7—C12—C11	120.7 (3)	N12—C38—H38A	109.8
C7—C12—H12	119.7	C37—C38—H38A	109.8
C11—C12—H12	119.7	N12—C38—H38B	109.7
N4—C13—C14	110.3 (2)	C37—C38—H38B	109.7
N4—C13—H13A	109.6	H38A—C38—H38B	108.2
C14—C13—H13A	109.6	P5—N7—P4	118.73 (12)
N4—C13—H13B	109.6	P6—N8—P5	124.13 (12)
C14—C13—H13B	109.6	P6—N9—P4	117.73 (12)
H13A—C13—H13B	108.1	C32—N10—P5	116.62 (14)
C13—C14—C15	111.0 (2)	C32—N10—H10N	110.0 (4)
C13—C14—H14A	109.4	P5—N10—H10N	114.8 (3)
C15—C14—H14A	109.4	C34—N11—C35	113.81 (18)
C13—C14—H14B	109.4	C34—N11—P5	120.43 (17)
C15—C14—H14B	109.4	C35—N11—P5	119.07 (14)
H14A—C14—H14B	108.0	C38—N12—P6	115.73 (17)
N5—C15—C14	113.1 (2)	C38—N12—H12N	120 (2)
N5—C15—H15A	109.0	P6—N12—H12N	109 (2)
C14—C15—H15A	109.0	N7—P4—N9	115.81 (10)
N5—C15—H15B	109.0	N7—P4—C20	106.98 (11)
C14—C15—H15B	109.0	N9—P4—C20	107.62 (11)
H15A—C15—H15B	107.8	N7—P4—C26	107.96 (10)
N5—C16—C17	141.22 (14)	N9—P4—C26	109.84 (11)
N5—C16—C17'	105.04 (13)	C20—P4—C26	108.38 (11)
C17—C16—C17'	37.78 (9)	N7—P5—N8	114.07 (11)
N5—C16—H16A	101.7	N7—P5—N10	110.02 (10)
C17—C16—H16A	101.7	N8—P5—N10	107.55 (9)
C17'—C16—H16A	131.9	N7—P5—N11	108.66 (10)
N5—C16—H16B	101.7	N8—P5—N11	111.35 (11)
C17—C16—H16B	101.7	N10—P5—N11	104.78 (10)
C17'—C16—H16B	108.0	N8—P6—N9	116.46 (10)
H16A—C16—H16B	104.7	N8—P6—N12	111.08 (11)
C16—C17—C18	115.60 (15)	N9—P6—N12	112.50 (10)
C16—C17—H17A	108.4	N8—P6—Cl2	108.62 (8)
C18—C17—H17A	108.4	N9—P6—Cl2	107.51 (8)
C16—C17—H17B	108.4	N12—P6—Cl2	99.10 (9)
C18—C17—H17B	108.4	C44—C39—C40	119.0 (2)
H17A—C17—H17B	107.4	C44—C39—P7	121.3 (2)
C18—C17'—C16	115.73 (15)	C40—C39—P7	119.7 (2)
C18—C17'—H17C	108.4	C41—C40—C39	119.0 (3)
C16—C17'—H17C	108.3	C41—C40—H40	120.5
C18—C17'—H17D	108.3	C39—C40—H40	120.5
C16—C17'—H17D	108.3	C42—C41—C40	121.5 (3)
H17C—C17'—H17D	107.4	C42—C41—H41	119.2
C19—C18—C17'	120.8 (2)	C40—C41—H41	119.2
C19—C18—C17	121.8 (2)	C41—C42—C43	119.1 (3)
C17'—C18—C17	37.81 (10)	C41—C42—H42	120.4
C19—C18—H18A	106.9	C43—C42—H42	120.4
C17'—C18—H18A	130.9	C44—C43—C42	120.5 (3)
C17—C18—H18A	106.9	C44—C43—H43	119.7
C19—C18—H18B	106.9	C42—C43—H43	119.7
C17'—C18—H18B	71.8	C43—C44—C39	120.7 (3)
C17—C18—H18B	106.9	C43—C44—H44	119.6
H18A—C18—H18B	106.7	C39—C44—H44	119.6
C18—C19—N6	118.8 (2)	C50—C45—C46	118.8 (2)
C18—C19—H19A	107.6	C50—C45—P7	122.0 (2)
N6—C19—H19A	107.6	C46—C45—P7	119.1 (2)
C18—C19—H19B	107.6	C45—C46—C47	120.2 (3)
N6—C19—H19B	107.6	C45—C46—H46	119.9
H19A—C19—H19B	107.0	C47—C46—H46	119.9
P2—N1—P1	122.35 (13)	C48—C47—C46	119.3 (3)
P3—N2—P2	123.78 (13)	C48—C47—H47	120.3
P3—N3—P1	120.82 (14)	C46—C47—H47	120.3
C13—N4—P2	115.92 (18)	C49—C48—C47	121.0 (3)
C13—N4—H4N	109.2 (18)	C49—C48—H48	119.5
P2—N4—H4N	112.9 (18)	C47—C48—H48	119.5
C16—N5—C15	112.6 (2)	C48—C49—C50	119.8 (3)
C16—N5—P2	116.59 (15)	C48—C49—H49	120.1
C15—N5—P2	120.52 (18)	C50—C49—H49	120.1
C19—N6—P3	116.33 (18)	C45—C50—C49	120.9 (3)
C19—N6—H6N	110.9 (18)	C45—C50—H50	119.5
P3—N6—H6N	116.5 (18)	C49—C50—H50	119.5
N1—P1—N3	116.79 (12)	N16—C51—C52	110.9 (2)
N1—P1—C7	108.74 (12)	N16—C51—H51A	109.5
N3—P1—C7	106.52 (12)	C52—C51—H51A	109.5
N1—P1—C1	111.37 (13)	N16—C51—H51B	109.5
N3—P1—C1	108.00 (13)	C52—C51—H51B	109.5
C7—P1—C1	104.65 (13)	H51A—C51—H51B	108.1
N1—P2—N2	114.90 (11)	C53—C52—C51	111.6 (2)
N1—P2—N4	108.00 (12)	C53—C52—H52A	109.3
N2—P2—N4	109.58 (11)	C51—C52—H52A	109.3
N1—P2—N5	109.79 (12)	C53—C52—H52B	109.3
N2—P2—N5	109.40 (12)	C51—C52—H52B	109.3
N4—P2—N5	104.68 (11)	H52A—C52—H52B	108.0
N2—P3—N3	116.99 (12)	N17—C53—C52	114.2 (2)
N2—P3—N6	112.73 (12)	N17—C53—H53A	108.7
N3—P3—N6	110.54 (12)	C52—C53—H53A	108.7
N2—P3—Cl1	106.73 (9)	N17—C53—H53B	108.7
N3—P3—Cl1	108.48 (9)	C52—C53—H53B	108.7
N6—P3—Cl1	99.77 (8)	H53A—C53—H53B	107.6
C25—C20—C21	118.8 (2)	N17—C54—C55	116.3 (2)
C25—C20—P4	119.40 (18)	N17—C54—H54A	108.2
C21—C20—P4	121.79 (19)	C55—C54—H54A	108.2
C20—C21—C22	119.9 (2)	N17—C54—H54B	108.2
C20—C21—H21	120.0	C55—C54—H54B	108.2
C22—C21—H21	120.0	H54A—C54—H54B	107.4
C23—C22—C21	121.2 (2)	C56—C55—C54	117.3 (2)
C23—C22—H22	119.4	C56—C55—H55A	108.0
C21—C22—H22	119.4	C54—C55—H55A	108.0
C22—C23—C24	118.9 (2)	C56—C55—H55B	108.0
C22—C23—H23	120.5	C54—C55—H55B	108.0
C24—C23—H23	120.5	H55A—C55—H55B	107.2
C25—C24—C23	120.3 (3)	C57—C56—C55	115.9 (2)
C25—C24—H24	119.9	C57—C56—H56A	108.3
C23—C24—H24	119.9	C55—C56—H56A	108.3
C24—C25—C20	120.8 (2)	C57—C56—H56B	108.3
C24—C25—H25	119.6	C55—C56—H56B	108.3
C20—C25—H25	119.6	H56A—C56—H56B	107.4
C31—C26—C27	118.5 (2)	N18—C57—C56	114.1 (2)
C31—C26—P4	120.77 (18)	N18—C57—H57A	108.7
C27—C26—P4	120.51 (18)	C56—C57—H57A	108.7
C28—C27—C26	120.3 (2)	N18—C57—H57B	108.7
C28—C27—H27	119.9	C56—C57—H57B	108.7
C26—C27—H27	119.9	H57A—C57—H57B	107.6
C29—C28—C27	120.4 (2)	P7—N13—P8	121.84 (13)
C29—C28—H28	119.8	P9—N14—P8	120.57 (13)
C27—C28—H28	119.8	P9—N15—P7	118.08 (13)
C28—C29—C30	119.8 (2)	C51—N16—P8	119.61 (18)
C28—C29—H29	120.1	C51—N16—H16N	113.8 (17)
C30—C29—H29	120.1	P8—N16—H16N	111.0 (17)
C31—C30—C29	120.2 (2)	C53—N17—C54	114.3 (2)
C31—C30—H30	119.9	C53—N17—P8	125.57 (18)
C29—C30—H30	119.9	C54—N17—P8	117.22 (17)
C30—C31—C26	120.9 (2)	C57—N18—P9	124.45 (18)
C30—C31—H31	119.5	C57—N18—H18N	115.4 (18)
C26—C31—H31	119.6	P9—N18—H18N	113.6 (18)
N10—C32—C33	111.05 (19)	N13—P7—N15	118.26 (11)
N10—C32—H32A	109.5	N13—P7—C39	107.85 (12)
C33—C32—H32A	109.4	N15—P7—C39	109.02 (11)
N10—C32—H32B	109.4	N13—P7—C45	109.70 (12)
C33—C32—H32B	109.4	N15—P7—C45	109.07 (12)
H32A—C32—H32B	108.0	C39—P7—C45	101.65 (11)
C34—C33—C32	112.1 (2)	N14—P8—N13	112.50 (11)
C34—C33—H33A	109.2	N14—P8—N16	110.26 (12)
C32—C33—H33A	109.2	N13—P8—N16	108.47 (11)
C34—C33—H33B	109.2	N14—P8—N17	109.46 (11)
C32—C33—H33B	109.2	N13—P8—N17	111.44 (11)
H33A—C33—H33B	107.9	N16—P8—N17	104.40 (12)
N11—C34—C33	112.4 (2)	N14—P9—N15	118.85 (11)
N11—C34—H34A	109.1	N14—P9—N18	111.35 (11)
C33—C34—H34A	109.1	N15—P9—N18	108.84 (11)
N11—C34—H34B	109.1	N14—P9—Cl3	104.28 (9)
C33—C34—H34B	109.1	N15—P9—Cl3	107.12 (9)
H34A—C34—H34B	107.9	N18—P9—Cl3	105.40 (9)
C6—C1—C2—C3	−0.6 (4)	C37—C38—N12—P6	87.8 (2)
P1—C1—C2—C3	179.3 (2)	P5—N7—P4—N9	−38.94 (16)
C1—C2—C3—C4	0.5 (5)	P5—N7—P4—C20	−158.89 (12)
C2—C3—C4—C5	−0.4 (5)	P5—N7—P4—C26	84.64 (14)
C3—C4—C5—C6	0.4 (5)	P6—N9—P4—N7	34.09 (16)
C4—C5—C6—C1	−0.5 (5)	P6—N9—P4—C20	153.69 (13)
C2—C1—C6—C5	0.6 (5)	P6—N9—P4—C26	−88.51 (15)
P1—C1—C6—C5	−179.3 (3)	C25—C20—P4—N7	−48.9 (2)
C12—C7—C8—C9	0.9 (4)	C21—C20—P4—N7	128.9 (2)
P1—C7—C8—C9	−179.3 (2)	C25—C20—P4—N9	−174.0 (2)
C7—C8—C9—C10	0.2 (5)	C21—C20—P4—N9	3.8 (2)
C8—C9—C10—C11	−0.8 (5)	C25—C20—P4—C26	67.2 (2)
C9—C10—C11—C12	0.2 (5)	C21—C20—P4—C26	−114.9 (2)
C8—C7—C12—C11	−1.5 (4)	C31—C26—P4—N7	26.0 (2)
P1—C7—C12—C11	178.7 (2)	C27—C26—P4—N7	−148.09 (18)
C10—C11—C12—C7	1.0 (5)	C31—C26—P4—N9	153.11 (18)
N4—C13—C14—C15	−64.6 (3)	C27—C26—P4—N9	−21.0 (2)
C13—C14—C15—N5	55.1 (3)	C31—C26—P4—C20	−89.6 (2)
N5—C16—C17—C18	78.5 (3)	C27—C26—P4—C20	96.4 (2)
C17'—C16—C17—C18	56.87 (14)	P4—N7—P5—N8	14.50 (16)
N5—C16—C17'—C18	136.68 (16)	P4—N7—P5—N10	−106.44 (13)
C17—C16—C17'—C18	−57.17 (14)	P4—N7—P5—N11	139.37 (12)
C16—C17'—C18—C19	−46.4 (2)	P6—N8—P5—N7	15.59 (18)
C16—C17'—C18—C17	57.05 (14)	P6—N8—P5—N10	137.90 (13)
C16—C17—C18—C19	43.6 (3)	P6—N8—P5—N11	−107.84 (15)
C16—C17—C18—C17'	−57.01 (14)	C32—N10—P5—N7	−158.18 (15)
C17'—C18—C19—N6	−73.1 (3)	C32—N10—P5—N8	77.03 (17)
C17—C18—C19—N6	−117.7 (2)	C32—N10—P5—N11	−41.54 (17)
C14—C13—N4—P2	60.5 (3)	C34—N11—P5—N7	153.58 (18)
C17—C16—N5—C15	40.3 (3)	C35—N11—P5—N7	−56.87 (18)
C17'—C16—N5—C15	53.9 (2)	C34—N11—P5—N8	−80.0 (2)
C17—C16—N5—P2	−105.2 (2)	C35—N11—P5—N8	69.59 (17)
C17'—C16—N5—P2	−91.62 (16)	C34—N11—P5—N10	36.0 (2)
C14—C15—N5—C16	173.8 (2)	C35—N11—P5—N10	−174.44 (14)
C14—C15—N5—P2	−42.3 (3)	P5—N8—P6—N9	−20.01 (18)
C18—C19—N6—P3	97.7 (3)	P5—N8—P6—N12	110.52 (15)
P2—N1—P1—N3	−14.1 (2)	P5—N8—P6—Cl2	−141.50 (12)
P2—N1—P1—C7	−134.63 (16)	P4—N9—P6—N8	−5.86 (17)
P2—N1—P1—C1	110.57 (17)	P4—N9—P6—N12	−135.73 (13)
P3—N3—P1—N1	19.6 (2)	P4—N9—P6—Cl2	116.21 (11)
P3—N3—P1—C7	141.23 (15)	C38—N12—P6—N8	−65.00 (19)
P3—N3—P1—C1	−106.83 (17)	C38—N12—P6—N9	67.57 (19)
C12—C7—P1—N1	121.0 (2)	C38—N12—P6—Cl2	−179.10 (15)
C8—C7—P1—N1	−58.7 (3)	C44—C39—C40—C41	3.1 (4)
C12—C7—P1—N3	−5.6 (3)	P7—C39—C40—C41	−175.3 (2)
C8—C7—P1—N3	174.7 (2)	C39—C40—C41—C42	−1.3 (5)
C12—C7—P1—C1	−119.9 (2)	C40—C41—C42—C43	−0.9 (5)
C8—C7—P1—C1	60.4 (3)	C41—C42—C43—C44	1.1 (4)
C2—C1—P1—N1	13.5 (3)	C42—C43—C44—C39	0.8 (4)
C6—C1—P1—N1	−166.6 (2)	C40—C39—C44—C43	−2.9 (4)
C2—C1—P1—N3	143.0 (2)	P7—C39—C44—C43	175.5 (2)
C6—C1—P1—N3	−37.1 (3)	C50—C45—C46—C47	0.9 (4)
C2—C1—P1—C7	−103.8 (2)	P7—C45—C46—C47	176.5 (2)
C6—C1—P1—C7	76.1 (2)	C45—C46—C47—C48	−1.0 (4)
P1—N1—P2—N2	−3.8 (2)	C46—C47—C48—C49	0.5 (5)
P1—N1—P2—N4	−126.44 (15)	C47—C48—C49—C50	0.1 (4)
P1—N1—P2—N5	119.98 (16)	C46—C45—C50—C49	−0.3 (4)
P3—N2—P2—N1	18.3 (2)	P7—C45—C50—C49	−175.8 (2)
P3—N2—P2—N4	140.11 (15)	C48—C49—C50—C45	−0.2 (4)
P3—N2—P2—N5	−105.66 (17)	N16—C51—C52—C53	−63.8 (3)
C13—N4—P2—N1	−159.13 (17)	C51—C52—C53—N17	48.4 (3)
C13—N4—P2—N2	75.04 (19)	N17—C54—C55—C56	49.1 (3)
C13—N4—P2—N5	−42.2 (2)	C54—C55—C56—C57	84.5 (3)
C16—N5—P2—N1	−67.88 (18)	C55—C56—C57—N18	−48.3 (3)
C15—N5—P2—N1	149.5 (2)	C52—C51—N16—P8	56.0 (3)
C16—N5—P2—N2	59.07 (18)	C52—C53—N17—C54	173.6 (2)
C15—N5—P2—N2	−83.6 (2)	C52—C53—N17—P8	−26.2 (3)
C16—N5—P2—N4	176.42 (14)	C55—C54—N17—C53	54.9 (3)
C15—N5—P2—N4	33.8 (2)	C55—C54—N17—P8	−107.0 (2)
P2—N2—P3—N3	−13.4 (2)	C56—C57—N18—P9	−70.5 (3)
P2—N2—P3—N6	116.45 (16)	P8—N13—P7—N15	−9.7 (2)
P2—N2—P3—Cl1	−135.01 (13)	P8—N13—P7—C39	−133.83 (15)
P1—N3—P3—N2	−6.5 (2)	P8—N13—P7—C45	116.25 (15)
P1—N3—P3—N6	−137.34 (15)	P9—N15—P7—N13	17.93 (19)
P1—N3—P3—Cl1	114.21 (14)	P9—N15—P7—C39	141.53 (14)
C19—N6—P3—N2	−72.9 (2)	P9—N15—P7—C45	−108.28 (15)
C19—N6—P3—N3	60.1 (2)	C44—C39—P7—N13	−162.3 (2)
C19—N6—P3—Cl1	174.17 (18)	C40—C39—P7—N13	16.0 (2)
C25—C20—C21—C22	0.9 (4)	C44—C39—P7—N15	68.1 (2)
P4—C20—C21—C22	−176.97 (19)	C40—C39—P7—N15	−113.5 (2)
C20—C21—C22—C23	0.8 (4)	C44—C39—P7—C45	−47.0 (2)
C21—C22—C23—C24	−1.6 (4)	C40—C39—P7—C45	131.4 (2)
C22—C23—C24—C25	0.7 (4)	C50—C45—P7—N13	−143.0 (2)
C23—C24—C25—C20	1.0 (4)	C46—C45—P7—N13	41.5 (2)
C21—C20—C25—C24	−1.8 (4)	C50—C45—P7—N15	−12.0 (2)
P4—C20—C25—C24	176.1 (2)	C46—C45—P7—N15	172.5 (2)
C31—C26—C27—C28	−0.1 (3)	C50—C45—P7—C39	103.0 (2)
P4—C26—C27—C28	174.07 (18)	C46—C45—P7—C39	−72.4 (2)
C26—C27—C28—C29	−0.4 (4)	P9—N14—P8—N13	35.02 (18)
C27—C28—C29—C30	1.2 (4)	P9—N14—P8—N16	156.24 (13)
C28—C29—C30—C31	−1.3 (4)	P9—N14—P8—N17	−89.45 (16)
C29—C30—C31—C26	0.8 (4)	P7—N13—P8—N14	−15.73 (19)
C27—C26—C31—C30	0.0 (4)	P7—N13—P8—N16	−137.98 (15)
P4—C26—C31—C30	−174.24 (19)	P7—N13—P8—N17	107.64 (15)
N10—C32—C33—C34	−61.8 (3)	C51—N16—P8—N14	87.8 (2)
C32—C33—C34—N11	55.0 (3)	C51—N16—P8—N13	−148.6 (2)
N11—C35—C36—C37	60.4 (4)	C51—N16—P8—N17	−29.7 (2)
C36'—C35—C36—C37	45.4 (3)	C53—N17—P8—N14	−103.0 (2)
N11—C35—C36'—C37	132.6 (5)	C54—N17—P8—N14	56.6 (2)
C36—C35—C36'—C37	−59.6 (5)	C53—N17—P8—N13	131.9 (2)
C35—C36'—C37—C36	52.1 (4)	C54—N17—P8—N13	−68.46 (19)
C35—C36'—C37—C38	−35.3 (7)	C53—N17—P8—N16	15.0 (2)
C35—C36—C37—C36'	−55.1 (3)	C54—N17—P8—N16	174.66 (17)
C35—C36—C37—C38	64.2 (4)	P8—N14—P9—N15	−28.21 (19)
C36'—C37—C38—N12	−92.4 (5)	P8—N14—P9—N18	99.46 (15)
C36—C37—C38—N12	−140.4 (3)	P8—N14—P9—Cl3	−147.36 (12)
C33—C32—N10—P5	56.9 (2)	P7—N15—P9—N14	0.2 (2)
C33—C34—N11—C35	164.10 (19)	P7—N15—P9—N18	−128.61 (14)
C33—C34—N11—P5	−44.9 (3)	P7—N15—P9—Cl3	117.89 (13)
C36—C35—N11—C34	51.8 (3)	C57—N18—P9—N14	33.0 (2)
C36'—C35—N11—C34	60.9 (2)	C57—N18—P9—N15	165.9 (2)
C36—C35—N11—P5	−99.7 (3)	C57—N18—P9—Cl3	−79.5 (2)
C36'—C35—N11—P5	−90.5 (2)

(II)

Crystal data

C19H26ClN6P3	F(000) = 1952
Mr = 466.82	Dx = 1.391 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.163 (3) Å	Cell parameters from 10998 reflections
b = 16.298 (3) Å	θ = 2.9–27.5°
c = 17.401 (4) Å	µ = 0.41 mm^−1
β = 103.36 (3)°	T = 120 K
V = 4459.7 (15) Å^3	Plate, colourless
Z = 8	0.2 × 0.1 × 0.01 mm

Data collection

Nonius KappaCCD area-detector diffractometer	3119 reflections with I > 2σ(I)
ϕ and ω scans	Rint = 0.125
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	θmax = 27.5°, θmin = 3.1°
Tmin = 0.923, Tmax = 0.998	h = −20→20
20266 measured reflections	k = −21→21
5053 independent reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.054	w = 1/[σ^2(Fo^2) + (0.0486P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.125	(Δ/σ)max = 0.004
S = 0.99	Δρmax = 0.36 e Å^−3
5053 reflections	Δρmin = −0.46 e Å^−3
271 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
H6N	0.1965 (18)	0.1702 (17)	0.4645 (17)	0.008 (8)*
H4N	0.4170 (18)	0.1591 (17)	0.1983 (17)	0.008 (8)*
C1	0.42780 (18)	0.36418 (18)	0.36553 (18)	0.0241 (7)
C2	0.4102 (2)	0.3729 (2)	0.2845 (2)	0.0327 (8)
H2	0.4079	0.3257	0.2521	0.039*
C3	0.3961 (2)	0.4495 (2)	0.2499 (2)	0.0411 (9)
H3	0.385	0.4549	0.1941	0.049*
C4	0.3982 (2)	0.5185 (2)	0.2970 (2)	0.0431 (10)
H4	0.3876	0.5712	0.2735	0.052*
C5	0.4156 (2)	0.5105 (2)	0.3781 (2)	0.0434 (10)
H5	0.4177	0.5578	0.4103	0.052*
C6	0.4300 (2)	0.43410 (19)	0.4123 (2)	0.0351 (9)
H6	0.4415	0.4289	0.4682	0.042*
C7	0.52253 (19)	0.26647 (17)	0.49500 (18)	0.0223 (7)
C8	0.6045 (2)	0.28115 (19)	0.4867 (2)	0.0302 (8)
H8	0.6147	0.289	0.4356	0.036*
C9	0.6720 (2)	0.2844 (2)	0.5533 (2)	0.0347 (8)
H9	0.7281	0.2949	0.5475	0.042*
C10	0.6572 (2)	0.27223 (19)	0.6274 (2)	0.0310 (8)
H10	0.703	0.2744	0.6727	0.037*
C11	0.5764 (2)	0.25714 (19)	0.63570 (19)	0.0314 (8)
H11	0.5668	0.2484	0.6869	0.038*
C12	0.5082 (2)	0.25444 (18)	0.57012 (18)	0.0283 (8)
H12	0.4523	0.2445	0.5765	0.034*
C13	0.3362 (2)	0.07773 (18)	0.15500 (18)	0.0264 (7)
H13A	0.3386	0.0889	0.0996	0.032*
H13B	0.2756	0.0727	0.1569	0.032*
C14	0.3814 (2)	−0.00197 (18)	0.18165 (17)	0.0256 (7)
H14A	0.4421	0.0033	0.1802	0.031*
H14B	0.3562	−0.0462	0.1446	0.031*
C15	0.3753 (2)	−0.02545 (18)	0.26466 (18)	0.0260 (7)
H15A	0.3152	−0.0372	0.2647	0.031*
H15B	0.4086	−0.0761	0.2808	0.031*
C16	0.42570 (19)	0.01382 (19)	0.40587 (17)	0.0250 (7)
H16A	0.4359	0.0636	0.4393	0.03*
H16B	0.4794	−0.0179	0.4167	0.03*
C17	0.3585 (2)	−0.03777 (19)	0.43218 (19)	0.0287 (8)
H17A	0.3809	−0.0531	0.4882	0.034*
H17B	0.3507	−0.0892	0.401	0.034*
C18	0.2711 (2)	0.00195 (18)	0.42457 (18)	0.0265 (7)
H18A	0.2312	−0.0404	0.435	0.032*
H18B	0.2501	0.0207	0.3694	0.032*
C19	0.2693 (2)	0.07484 (18)	0.47973 (17)	0.0253 (7)
H19A	0.2442	0.0569	0.5238	0.03*
H19B	0.3283	0.0929	0.5026	0.03*
N1	0.45432 (15)	0.19633 (14)	0.34809 (14)	0.0214 (6)
N2	0.28675 (15)	0.15504 (14)	0.31403 (13)	0.0195 (6)
N3	0.34976 (15)	0.24846 (15)	0.44175 (14)	0.0229 (6)
N4	0.37503 (18)	0.14686 (16)	0.20538 (15)	0.0217 (6)
N5	0.40726 (15)	0.04013 (14)	0.32244 (14)	0.0211 (6)
N6	0.21975 (17)	0.14502 (16)	0.43906 (16)	0.0227 (6)
P1	0.43457 (5)	0.26312 (5)	0.40941 (5)	0.0204 (2)
P2	0.38028 (5)	0.13773 (5)	0.30062 (4)	0.0191 (2)
P3	0.26993 (5)	0.20260 (5)	0.38743 (4)	0.0199 (2)
Cl1	0.17833 (5)	0.28921 (5)	0.34667 (4)	0.0273 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0189 (15)	0.0237 (16)	0.0280 (18)	0.0001 (13)	0.0022 (13)	−0.0012 (14)
C2	0.0348 (19)	0.0330 (19)	0.0285 (19)	0.0027 (16)	0.0038 (15)	0.0012 (15)
C3	0.044 (2)	0.044 (2)	0.031 (2)	0.0074 (18)	0.0014 (17)	0.0121 (17)
C4	0.040 (2)	0.032 (2)	0.053 (3)	0.0053 (17)	0.0007 (19)	0.0094 (18)
C5	0.054 (2)	0.0233 (18)	0.049 (3)	0.0015 (17)	0.004 (2)	−0.0014 (17)
C6	0.044 (2)	0.0298 (18)	0.030 (2)	0.0008 (16)	0.0059 (17)	−0.0045 (15)
C7	0.0236 (16)	0.0221 (15)	0.0193 (17)	−0.0011 (13)	0.0012 (13)	−0.0036 (13)
C8	0.0275 (18)	0.0403 (19)	0.0237 (18)	−0.0035 (15)	0.0080 (14)	−0.0079 (15)
C9	0.0233 (17)	0.043 (2)	0.035 (2)	−0.0051 (16)	0.0011 (15)	−0.0125 (16)
C10	0.0282 (19)	0.0309 (18)	0.0277 (19)	0.0038 (15)	−0.0063 (15)	−0.0068 (14)
C11	0.038 (2)	0.0321 (18)	0.0196 (17)	−0.0018 (16)	−0.0017 (15)	0.0023 (14)
C12	0.0274 (18)	0.0302 (18)	0.0261 (19)	0.0008 (15)	0.0040 (15)	−0.0001 (14)
C13	0.0296 (18)	0.0312 (17)	0.0174 (17)	−0.0030 (15)	0.0036 (14)	−0.0018 (14)
C14	0.0327 (18)	0.0250 (16)	0.0185 (17)	−0.0049 (15)	0.0049 (14)	−0.0060 (13)
C15	0.0306 (18)	0.0249 (17)	0.0235 (18)	−0.0016 (14)	0.0084 (15)	−0.0012 (13)
C16	0.0252 (17)	0.0303 (17)	0.0175 (17)	0.0068 (14)	0.0010 (14)	0.0054 (13)
C17	0.038 (2)	0.0252 (16)	0.0238 (18)	0.0038 (15)	0.0084 (15)	0.0038 (14)
C18	0.0306 (18)	0.0286 (17)	0.0207 (17)	−0.0052 (14)	0.0065 (14)	0.0016 (14)
C19	0.0267 (17)	0.0332 (17)	0.0160 (17)	0.0018 (14)	0.0053 (14)	0.0022 (13)
N1	0.0210 (13)	0.0262 (13)	0.0174 (13)	0.0000 (11)	0.0051 (11)	−0.0049 (11)
N2	0.0183 (13)	0.0270 (13)	0.0131 (13)	−0.0018 (11)	0.0031 (10)	−0.0031 (10)
N3	0.0225 (14)	0.0286 (14)	0.0170 (13)	−0.0018 (11)	0.0036 (11)	−0.0083 (11)
N4	0.0202 (15)	0.0301 (15)	0.0156 (14)	−0.0036 (12)	0.0062 (12)	−0.0041 (11)
N5	0.0279 (14)	0.0212 (12)	0.0141 (13)	−0.0013 (11)	0.0046 (11)	−0.0014 (11)
N6	0.0225 (14)	0.0277 (15)	0.0192 (14)	0.0029 (12)	0.0074 (12)	−0.0029 (12)
P1	0.0201 (4)	0.0232 (4)	0.0173 (4)	−0.0012 (3)	0.0032 (3)	−0.0035 (3)
P2	0.0203 (4)	0.0214 (4)	0.0151 (4)	0.0003 (3)	0.0029 (3)	−0.0013 (3)
P3	0.0195 (4)	0.0239 (4)	0.0159 (4)	0.0004 (3)	0.0028 (3)	−0.0012 (3)
Cl1	0.0277 (4)	0.0306 (4)	0.0232 (4)	0.0085 (3)	0.0048 (3)	0.0018 (3)

Geometric parameters (Å, º)

C1—C2	1.380 (4)	C14—H14B	0.99
C1—C6	1.396 (4)	C15—N5	1.477 (4)
C1—P1	1.808 (3)	C15—H15A	0.99
C2—C3	1.381 (5)	C15—H15B	0.99
C2—H2	0.95	C16—N5	1.477 (4)
C3—C4	1.387 (5)	C16—C17	1.525 (4)
C3—H3	0.95	C16—H16A	0.99
C4—C5	1.379 (5)	C16—H16B	0.99
C4—H4	0.95	C17—C18	1.532 (4)
C5—C6	1.377 (5)	C17—H17A	0.99
C5—H5	0.95	C17—H17B	0.99
C6—H6	0.95	C18—C19	1.532 (4)
C7—C8	1.386 (4)	C18—H18A	0.99
C7—C12	1.393 (4)	C18—H18B	0.99
C7—P1	1.807 (3)	C19—N6	1.479 (4)
C8—C9	1.398 (4)	C19—H19A	0.99
C8—H8	0.95	C19—H19B	0.99
C9—C10	1.380 (5)	N1—P2	1.603 (2)
C9—H9	0.95	N1—P1	1.607 (2)
C10—C11	1.368 (5)	N2—P3	1.571 (2)
C10—H10	0.95	N2—P2	1.607 (3)
C11—C12	1.392 (4)	N3—P3	1.598 (2)
C11—H11	0.95	N3—P1	1.615 (3)
C12—H12	0.95	N4—P2	1.646 (3)
C13—N4	1.476 (4)	N4—H4N	0.74 (3)
C13—C14	1.510 (4)	N5—P2	1.670 (2)
C13—H13A	0.99	N6—P3	1.638 (3)
C13—H13B	0.99	N6—H6N	0.76 (3)
C14—C15	1.519 (4)	P3—Cl1	2.0499 (11)
C14—H14A	0.99
C2—C1—C6	118.9 (3)	N5—C16—C17	117.3 (2)
C2—C1—P1	120.3 (2)	N5—C16—H16A	108
C6—C1—P1	120.4 (2)	C17—C16—H16A	108
C1—C2—C3	120.8 (3)	N5—C16—H16B	108
C1—C2—H2	119.6	C17—C16—H16B	108
C3—C2—H2	119.6	H16A—C16—H16B	107.2
C2—C3—C4	119.7 (3)	C16—C17—C18	116.6 (2)
C2—C3—H3	120.1	C16—C17—H17A	108.1
C4—C3—H3	120.1	C18—C17—H17A	108.1
C5—C4—C3	119.9 (3)	C16—C17—H17B	108.1
C5—C4—H4	120	C18—C17—H17B	108.1
C3—C4—H4	120	H17A—C17—H17B	107.3
C6—C5—C4	120.2 (3)	C17—C18—C19	115.1 (3)
C6—C5—H5	119.9	C17—C18—H18A	108.5
C4—C5—H5	119.9	C19—C18—H18A	108.5
C5—C6—C1	120.4 (3)	C17—C18—H18B	108.5
C5—C6—H6	119.8	C19—C18—H18B	108.5
C1—C6—H6	119.8	H18A—C18—H18B	107.5
C8—C7—C12	119.5 (3)	N6—C19—C18	112.7 (2)
C8—C7—P1	120.5 (2)	N6—C19—H19A	109
C12—C7—P1	120.0 (2)	C18—C19—H19A	109
C7—C8—C9	120.1 (3)	N6—C19—H19B	109
C7—C8—H8	119.9	C18—C19—H19B	109
C9—C8—H8	119.9	H19A—C19—H19B	107.8
C10—C9—C8	119.9 (3)	P2—N1—P1	120.43 (16)
C10—C9—H9	120.1	P3—N2—P2	123.38 (14)
C8—C9—H9	120.1	P3—N3—P1	119.83 (15)
C11—C10—C9	120.1 (3)	C13—N4—P2	116.4 (2)
C11—C10—H10	120	C13—N4—H4N	113 (2)
C9—C10—H10	120	P2—N4—H4N	111 (2)
C10—C11—C12	120.9 (3)	C16—N5—C15	114.7 (2)
C10—C11—H11	119.6	C16—N5—P2	118.89 (19)
C12—C11—H11	119.6	C15—N5—P2	120.19 (18)
C7—C12—C11	119.5 (3)	C19—N6—P3	115.1 (2)
C7—C12—H12	120.2	C19—N6—H6N	115 (2)
C11—C12—H12	120.2	P3—N6—H6N	113 (2)
N4—C13—C14	111.4 (2)	N1—P1—N3	116.48 (13)
N4—C13—H13A	109.3	N1—P1—C7	109.18 (13)
C14—C13—H13A	109.3	N3—P1—C7	106.67 (14)
N4—C13—H13B	109.3	N1—P1—C1	109.79 (14)
C14—C13—H13B	109.3	N3—P1—C1	107.97 (14)
H13A—C13—H13B	108	C7—P1—C1	106.26 (13)
C13—C14—C15	112.0 (3)	N1—P2—N2	115.84 (13)
C13—C14—H14A	109.2	N1—P2—N4	108.88 (14)
C15—C14—H14A	109.2	N2—P2—N4	107.40 (14)
C13—C14—H14B	109.2	N1—P2—N5	109.00 (12)
C15—C14—H14B	109.2	N2—P2—N5	109.83 (13)
H14A—C14—H14B	107.9	N4—P2—N5	105.37 (13)
N5—C15—C14	112.1 (2)	N2—P3—N3	116.36 (13)
N5—C15—H15A	109.2	N2—P3—N6	111.35 (14)
C14—C15—H15A	109.2	N3—P3—N6	112.22 (14)
N5—C15—H15B	109.2	N2—P3—Cl1	107.78 (9)
C14—C15—H15B	109.2	N3—P3—Cl1	107.61 (10)
H15A—C15—H15B	107.9	N6—P3—Cl1	100.06 (11)
C6—C1—C2—C3	0.8 (5)	C8—C7—P1—N3	−177.8 (2)
P1—C1—C2—C3	173.2 (3)	C12—C7—P1—N3	2.0 (3)
C1—C2—C3—C4	−1.0 (5)	C8—C7—P1—C1	−62.8 (3)
C2—C3—C4—C5	1.0 (6)	C12—C7—P1—C1	117.0 (3)
C3—C4—C5—C6	−0.7 (6)	C2—C1—P1—N1	22.0 (3)
C4—C5—C6—C1	0.5 (6)	C6—C1—P1—N1	−165.7 (2)
C2—C1—C6—C5	−0.5 (5)	C2—C1—P1—N3	−105.9 (3)
P1—C1—C6—C5	−172.9 (3)	C6—C1—P1—N3	66.3 (3)
C12—C7—C8—C9	−0.4 (5)	C2—C1—P1—C7	140.0 (3)
P1—C7—C8—C9	179.4 (2)	C6—C1—P1—C7	−47.8 (3)
C7—C8—C9—C10	0.5 (5)	P1—N1—P2—N2	4.2 (2)
C8—C9—C10—C11	−0.1 (5)	P1—N1—P2—N4	125.28 (17)
C9—C10—C11—C12	−0.5 (5)	P1—N1—P2—N5	−120.26 (17)
C8—C7—C12—C11	−0.2 (5)	P3—N2—P2—N1	−20.5 (2)
P1—C7—C12—C11	180.0 (2)	P3—N2—P2—N4	−142.38 (17)
C10—C11—C12—C7	0.6 (5)	P3—N2—P2—N5	103.53 (18)
N4—C13—C14—C15	62.6 (3)	C13—N4—P2—N1	157.3 (2)
C13—C14—C15—N5	−55.5 (3)	C13—N4—P2—N2	−76.6 (2)
N5—C16—C17—C18	−60.9 (4)	C13—N4—P2—N5	40.5 (3)
C16—C17—C18—C19	−67.4 (4)	C16—N5—P2—N1	57.2 (2)
C17—C18—C19—N6	135.0 (3)	C15—N5—P2—N1	−151.8 (2)
C14—C13—N4—P2	−56.7 (3)	C16—N5—P2—N2	−70.7 (2)
C17—C16—N5—C15	−47.2 (4)	C15—N5—P2—N2	80.3 (3)
C17—C16—N5—P2	105.3 (3)	C16—N5—P2—N4	174.0 (2)
C14—C15—N5—C16	−163.7 (3)	C15—N5—P2—N4	−35.1 (3)
C14—C15—N5—P2	44.2 (3)	P2—N2—P3—N3	11.0 (2)
C18—C19—N6—P3	−79.9 (3)	P2—N2—P3—N6	−119.29 (18)
P2—N1—P1—N3	19.6 (2)	P2—N2—P3—Cl1	131.90 (15)
P2—N1—P1—C7	140.46 (17)	P1—N3—P3—N2	14.8 (2)
P2—N1—P1—C1	−103.43 (18)	P1—N3—P3—N6	144.69 (17)
P3—N3—P1—N1	−29.7 (2)	P1—N3—P3—Cl1	−106.18 (15)
P3—N3—P1—C7	−151.91 (16)	C19—N6—P3—N2	67.5 (2)
P3—N3—P1—C1	94.24 (19)	C19—N6—P3—N3	−64.9 (2)
C8—C7—P1—N1	55.5 (3)	C19—N6—P3—Cl1	−178.79 (19)
C12—C7—P1—N1	−124.6 (2)