2-(4-Methyl-pyridin-2-yl)-4',4',6',6'-tetra-kis-(pyrrolidin-1-yl)-1H,2H-spiro-[naphtho-[1,2-e][1,3,2]oxaza-phosphinine-3,2'-[1,3,5,2,4,6]tri-aza-triphosphinine].

In the title spiro-phosphazene derivative, C33H46N9OP3, the phosphazene and six-membered N/O rings are in flattened chair and twisted-boat conformations, respectively. The naphthalene ring system and the pyridine ring are oriented at a dihedral angle of 41.82 (4)°. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules related by translation along the a axis into chains. C-H⋯π inter-actions aggregate these chains into layers parallel to the ab plane.

Related literature

For N/O-donor-type bifunctional reagents used for the reaction of hexa­chloro­cyclo­triphosphazene giving spiro derivatives, see: Beşli et al. (2007 ▶); Işıklan et al. (2010 ▶, 2013 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the standard compound, N3P3Cl6, see: Bullen (1971 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C33H46N9OP3

M = 677.70

Triclinic,

a = 9.5830 (2) Å

b = 10.9142 (2) Å

c = 16.8172 (3) Å

α = 79.210 (2)°

β = 84.542 (3)°

γ = 74.193 (2)°

V = 1660.68 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.31 × 0.26 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.934, T max = 0.947

30003 measured reflections

8270 independent reflections

6876 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.04

8270 reflections

416 parameters

H-atom parameters constrained

Δρmax = 0.89 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014220/cv5414sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014220/cv5414Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014220/cv5414Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C33H46N9OP3	Z = 2
Mr = 677.70	F(000) = 720
Triclinic, P1	Dx = 1.355 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5830 (2) Å	Cell parameters from 9939 reflections
b = 10.9142 (2) Å	θ = 2.2–28.3°
c = 16.8172 (3) Å	µ = 0.22 mm−1
α = 79.210 (2)°	T = 100 K
β = 84.542 (3)°	Block, colourless
γ = 74.193 (2)°	0.31 × 0.26 × 0.25 mm
V = 1660.68 (6) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	8270 independent reflections
Radiation source: fine-focus sealed tube	6876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 28.4°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.934, Tmax = 0.947	k = −14→14
30003 measured reflections	l = −21→22

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0556P)2 + 0.8708P] where P = (Fo2 + 2Fc2)/3
8270 reflections	(Δ/σ)max = 0.001
416 parameters	Δρmax = 0.89 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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.

	x	y	z	Uiso*/Ueq
P1	0.41615 (4)	0.65219 (4)	0.26913 (2)	0.01269 (9)
P2	0.42634 (4)	0.90846 (4)	0.24147 (2)	0.01288 (9)
P3	0.36895 (4)	0.78543 (4)	0.39892 (2)	0.01263 (9)
O1	0.26440 (11)	0.63318 (11)	0.24585 (7)	0.0168 (2)
N1	0.45484 (14)	0.77140 (12)	0.21130 (8)	0.0147 (3)
N2	0.40058 (14)	0.90563 (12)	0.33662 (8)	0.0156 (3)
N3	0.40214 (14)	0.65238 (12)	0.36308 (8)	0.0147 (3)
N4	0.52927 (14)	0.51427 (12)	0.24700 (8)	0.0140 (3)
N5	0.74070 (15)	0.34880 (13)	0.26606 (8)	0.0171 (3)
N6	0.56147 (14)	0.97631 (13)	0.21432 (8)	0.0165 (3)
N7	0.29558 (15)	1.00713 (12)	0.18643 (8)	0.0174 (3)
N8	0.45650 (14)	0.74826 (12)	0.48273 (8)	0.0156 (3)
N9	0.19774 (14)	0.83237 (12)	0.43381 (8)	0.0148 (3)
C1	0.34522 (17)	0.45778 (15)	0.07336 (9)	0.0153 (3)
C2	0.44802 (18)	0.35388 (15)	0.04381 (10)	0.0179 (3)
H2	0.5298	0.3100	0.0730	0.021*
C3	0.42865 (19)	0.31713 (16)	−0.02734 (10)	0.0211 (3)
H3	0.4971	0.2487	−0.0457	0.025*
C4	0.3060 (2)	0.38236 (17)	−0.07261 (10)	0.0234 (4)
H4	0.2931	0.3564	−0.1204	0.028*
C5	0.2061 (2)	0.48350 (16)	−0.04650 (10)	0.0230 (4)
H5	0.1261	0.5267	−0.0773	0.028*
C6	0.22176 (18)	0.52431 (15)	0.02693 (10)	0.0185 (3)
C7	0.11652 (19)	0.62697 (16)	0.05555 (11)	0.0229 (4)
H7	0.0355	0.6698	0.0255	0.027*
C8	0.13190 (18)	0.66438 (16)	0.12675 (11)	0.0216 (3)
H8	0.0627	0.7324	0.1451	0.026*
C9	0.25415 (17)	0.59798 (15)	0.17156 (10)	0.0163 (3)
C10	0.35985 (16)	0.49761 (14)	0.14797 (9)	0.0146 (3)
C11	0.48332 (17)	0.42860 (15)	0.20221 (10)	0.0170 (3)
H11A	0.4544	0.3611	0.2409	0.020*
H11B	0.5656	0.3876	0.1696	0.020*
C12	0.67301 (16)	0.47150 (14)	0.27157 (9)	0.0139 (3)
C13	0.74130 (17)	0.55364 (15)	0.29904 (10)	0.0165 (3)
H13	0.6903	0.6380	0.3035	0.020*
C14	0.88477 (17)	0.50805 (16)	0.31940 (10)	0.0182 (3)
C15	0.95706 (18)	0.38142 (16)	0.31073 (10)	0.0205 (3)
H15	1.0547	0.3480	0.3219	0.025*
C16	0.88029 (18)	0.30691 (16)	0.28526 (10)	0.0203 (3)
H16	0.9287	0.2219	0.2811	0.024*
C17	0.96028 (19)	0.59051 (18)	0.35269 (12)	0.0263 (4)
H17A	1.0582	0.5770	0.3303	0.039*
H17B	0.9613	0.5673	0.4106	0.039*
H17C	0.9095	0.6798	0.3383	0.039*
C18	0.68198 (18)	0.95919 (17)	0.26621 (11)	0.0225 (4)
H18A	0.7359	0.8692	0.2780	0.027*
H18B	0.6478	0.9906	0.3167	0.027*
C19	0.7737 (2)	1.0406 (2)	0.21450 (13)	0.0341 (5)
H19A	0.7362	1.1310	0.2194	0.041*
H19B	0.8738	1.0115	0.2301	0.041*
C20	0.7616 (2)	1.0203 (2)	0.12923 (13)	0.0352 (5)
H20A	0.8378	0.9470	0.1161	0.042*
H20B	0.7688	1.0964	0.0904	0.042*
C21	0.61243 (19)	0.99544 (17)	0.12823 (10)	0.0218 (3)
H21A	0.5465	1.0687	0.0972	0.026*
H21B	0.6199	0.9191	0.1047	0.026*
C22	0.20688 (19)	0.97192 (16)	0.13292 (11)	0.0218 (3)
H22A	0.1234	0.9483	0.1624	0.026*
H22B	0.2630	0.9008	0.1068	0.026*
C23	0.1608 (2)	1.09529 (17)	0.07164 (11)	0.0276 (4)
H23A	0.0726	1.0987	0.0464	0.033*
H23B	0.2366	1.1024	0.0298	0.033*
C24	0.13567 (19)	1.20106 (16)	0.12308 (11)	0.0227 (4)
H24A	0.0379	1.2185	0.1474	0.027*
H24B	0.1506	1.2802	0.0906	0.027*
C25	0.24817 (18)	1.14693 (15)	0.18844 (10)	0.0191 (3)
H25A	0.3293	1.1856	0.1761	0.023*
H25B	0.2049	1.1631	0.2413	0.023*
C26	0.60087 (18)	0.65564 (17)	0.49101 (10)	0.0212 (3)
H26A	0.6708	0.6825	0.4507	0.025*
H26B	0.5966	0.5696	0.4861	0.025*
C27	0.63870 (18)	0.66012 (15)	0.57564 (10)	0.0202 (3)
H27A	0.7429	0.6326	0.5815	0.024*
H27B	0.5927	0.6061	0.6162	0.024*
C28	0.57847 (19)	0.80239 (16)	0.58221 (11)	0.0236 (4)
H28A	0.6430	0.8531	0.5545	0.028*
H28B	0.5636	0.8144	0.6384	0.028*
C29	0.43433 (18)	0.83939 (16)	0.54080 (10)	0.0190 (3)
H29A	0.3554	0.8293	0.5799	0.023*
H29B	0.4130	0.9281	0.5127	0.023*
C30	0.13884 (17)	0.73570 (16)	0.49065 (10)	0.0196 (3)
H30A	0.1860	0.7133	0.5419	0.023*
H30B	0.1512	0.6578	0.4679	0.023*
C31	−0.02248 (18)	0.80459 (18)	0.50156 (11)	0.0239 (4)
H31A	−0.0403	0.8431	0.5503	0.029*
H31B	−0.0818	0.7444	0.5053	0.029*
C32	−0.05706 (18)	0.90933 (18)	0.42606 (11)	0.0235 (4)
H32A	−0.1318	0.8957	0.3962	0.028*
H32B	−0.0903	0.9944	0.4412	0.028*
C33	0.08559 (17)	0.89666 (16)	0.37477 (10)	0.0196 (3)
H33A	0.0893	0.8448	0.3333	0.024*
H33B	0.0972	0.9808	0.3491	0.024*

	U11	U22	U33	U12	U13	U23
P1	0.01320 (18)	0.01268 (18)	0.01255 (19)	−0.00217 (14)	−0.00114 (14)	−0.00448 (14)
P2	0.01397 (19)	0.01263 (18)	0.01200 (19)	−0.00272 (14)	−0.00155 (14)	−0.00256 (14)
P3	0.01362 (18)	0.01335 (18)	0.01120 (19)	−0.00266 (14)	−0.00087 (14)	−0.00389 (14)
O1	0.0142 (5)	0.0201 (6)	0.0184 (6)	−0.0037 (4)	−0.0011 (4)	−0.0098 (5)
N1	0.0180 (6)	0.0132 (6)	0.0123 (6)	−0.0015 (5)	−0.0009 (5)	−0.0040 (5)
N2	0.0210 (7)	0.0139 (6)	0.0131 (6)	−0.0055 (5)	−0.0005 (5)	−0.0037 (5)
N3	0.0188 (6)	0.0135 (6)	0.0120 (6)	−0.0037 (5)	−0.0009 (5)	−0.0033 (5)
N4	0.0147 (6)	0.0130 (6)	0.0153 (6)	−0.0022 (5)	−0.0023 (5)	−0.0058 (5)
N5	0.0189 (7)	0.0166 (6)	0.0150 (7)	−0.0013 (5)	−0.0030 (5)	−0.0041 (5)
N6	0.0165 (6)	0.0201 (7)	0.0134 (7)	−0.0064 (5)	−0.0025 (5)	−0.0008 (5)
N7	0.0195 (7)	0.0136 (6)	0.0194 (7)	−0.0018 (5)	−0.0070 (5)	−0.0041 (5)
N8	0.0150 (6)	0.0164 (6)	0.0146 (7)	0.0001 (5)	−0.0028 (5)	−0.0063 (5)
N9	0.0125 (6)	0.0178 (6)	0.0138 (6)	−0.0026 (5)	−0.0016 (5)	−0.0037 (5)
C1	0.0189 (7)	0.0153 (7)	0.0137 (7)	−0.0079 (6)	−0.0012 (6)	−0.0019 (6)
C2	0.0208 (8)	0.0198 (8)	0.0148 (8)	−0.0078 (6)	−0.0006 (6)	−0.0039 (6)
C3	0.0281 (9)	0.0221 (8)	0.0162 (8)	−0.0103 (7)	0.0025 (7)	−0.0069 (6)
C4	0.0371 (10)	0.0261 (9)	0.0118 (8)	−0.0157 (8)	−0.0021 (7)	−0.0031 (6)
C5	0.0319 (9)	0.0228 (8)	0.0168 (8)	−0.0123 (7)	−0.0103 (7)	0.0025 (6)
C6	0.0238 (8)	0.0163 (7)	0.0173 (8)	−0.0083 (6)	−0.0061 (6)	−0.0003 (6)
C7	0.0234 (8)	0.0187 (8)	0.0270 (9)	−0.0035 (7)	−0.0127 (7)	−0.0022 (7)
C8	0.0189 (8)	0.0165 (8)	0.0294 (9)	−0.0007 (6)	−0.0063 (7)	−0.0072 (7)
C9	0.0170 (7)	0.0172 (7)	0.0171 (8)	−0.0062 (6)	−0.0029 (6)	−0.0054 (6)
C10	0.0162 (7)	0.0147 (7)	0.0145 (8)	−0.0058 (6)	−0.0023 (6)	−0.0031 (6)
C11	0.0198 (8)	0.0145 (7)	0.0182 (8)	−0.0025 (6)	−0.0053 (6)	−0.0072 (6)
C12	0.0148 (7)	0.0158 (7)	0.0101 (7)	−0.0024 (6)	−0.0002 (6)	−0.0023 (6)
C13	0.0169 (7)	0.0157 (7)	0.0168 (8)	−0.0025 (6)	−0.0003 (6)	−0.0051 (6)
C14	0.0165 (7)	0.0231 (8)	0.0154 (8)	−0.0051 (6)	−0.0009 (6)	−0.0046 (6)
C15	0.0154 (7)	0.0247 (8)	0.0195 (8)	−0.0003 (6)	−0.0036 (6)	−0.0052 (7)
C16	0.0200 (8)	0.0175 (8)	0.0203 (8)	0.0023 (6)	−0.0031 (6)	−0.0053 (6)
C17	0.0183 (8)	0.0290 (9)	0.0349 (10)	−0.0065 (7)	−0.0049 (7)	−0.0111 (8)
C18	0.0196 (8)	0.0254 (9)	0.0240 (9)	−0.0067 (7)	−0.0065 (7)	−0.0039 (7)
C19	0.0261 (10)	0.0422 (11)	0.0402 (12)	−0.0167 (9)	0.0005 (8)	−0.0114 (9)
C20	0.0250 (10)	0.0495 (13)	0.0313 (11)	−0.0156 (9)	0.0047 (8)	−0.0021 (9)
C21	0.0243 (8)	0.0238 (8)	0.0178 (8)	−0.0090 (7)	0.0037 (7)	−0.0029 (6)
C22	0.0221 (8)	0.0183 (8)	0.0260 (9)	−0.0033 (6)	−0.0105 (7)	−0.0047 (7)
C23	0.0331 (10)	0.0263 (9)	0.0220 (9)	−0.0028 (8)	−0.0094 (8)	−0.0034 (7)
C24	0.0258 (9)	0.0170 (8)	0.0221 (9)	0.0001 (6)	−0.0063 (7)	−0.0011 (6)
C25	0.0217 (8)	0.0138 (7)	0.0202 (8)	−0.0009 (6)	−0.0039 (6)	−0.0031 (6)
C26	0.0175 (8)	0.0236 (8)	0.0192 (8)	0.0026 (6)	−0.0046 (6)	−0.0052 (7)
C27	0.0217 (8)	0.0179 (8)	0.0207 (8)	−0.0044 (6)	−0.0079 (7)	−0.0002 (6)
C28	0.0277 (9)	0.0209 (8)	0.0246 (9)	−0.0068 (7)	−0.0122 (7)	−0.0038 (7)
C29	0.0225 (8)	0.0188 (8)	0.0166 (8)	−0.0033 (6)	−0.0033 (6)	−0.0069 (6)
C30	0.0171 (8)	0.0234 (8)	0.0184 (8)	−0.0068 (6)	0.0002 (6)	−0.0025 (6)
C31	0.0179 (8)	0.0311 (9)	0.0248 (9)	−0.0079 (7)	0.0033 (7)	−0.0095 (7)
C32	0.0154 (8)	0.0302 (9)	0.0253 (9)	−0.0026 (7)	−0.0041 (7)	−0.0092 (7)
C33	0.0171 (8)	0.0226 (8)	0.0178 (8)	−0.0007 (6)	−0.0043 (6)	−0.0050 (6)

P1—O1	1.6168 (11)	C15—C16	1.379 (2)
P1—N1	1.5801 (13)	C15—H15	0.9300
P1—N3	1.5732 (13)	C16—H16	0.9300
P1—N4	1.6804 (13)	C17—H17A	0.9600
P2—N1	1.6140 (13)	C17—H17B	0.9600
P2—N2	1.5914 (13)	C17—H17C	0.9600
P2—N6	1.6483 (14)	C18—C19	1.519 (3)
P2—N7	1.6430 (14)	C18—H18A	0.9700
P3—N2	1.5975 (13)	C18—H18B	0.9700
P3—N3	1.6164 (13)	C19—H19A	0.9700
P3—N8	1.6372 (14)	C19—H19B	0.9700
P3—N9	1.6644 (13)	C20—C19	1.511 (3)
O1—C9	1.3934 (18)	C20—H20A	0.9700
N4—C11	1.4787 (19)	C20—H20B	0.9700
N4—C12	1.4043 (19)	C21—C20	1.528 (2)
N5—C12	1.3359 (19)	C21—H21A	0.9700
N5—C16	1.340 (2)	C21—H21B	0.9700
N6—C18	1.464 (2)	C22—C23	1.521 (2)
N6—C21	1.479 (2)	C22—H22A	0.9700
N7—C22	1.460 (2)	C22—H22B	0.9700
N7—C25	1.4746 (19)	C23—C24	1.524 (2)
N8—C26	1.476 (2)	C23—H23A	0.9700
N8—C29	1.4823 (19)	C23—H23B	0.9700
N9—C30	1.480 (2)	C24—H24A	0.9700
N9—C33	1.471 (2)	C24—H24B	0.9700
C1—C2	1.419 (2)	C25—C24	1.535 (2)
C1—C6	1.426 (2)	C25—H25A	0.9700
C1—C10	1.433 (2)	C25—H25B	0.9700
C2—C3	1.375 (2)	C26—C27	1.514 (2)
C2—H2	0.9300	C26—H26A	0.9700
C3—C4	1.407 (3)	C26—H26B	0.9700
C3—H3	0.9300	C27—C28	1.523 (2)
C4—C5	1.361 (3)	C27—H27A	0.9700
C4—H4	0.9300	C27—H27B	0.9700
C5—H5	0.9300	C28—H28A	0.9700
C6—C5	1.422 (2)	C28—H28B	0.9700
C6—C7	1.414 (2)	C29—C28	1.526 (2)
C7—C8	1.368 (2)	C29—H29A	0.9700
C7—H7	0.9300	C29—H29B	0.9700
C8—H8	0.9300	C30—C31	1.534 (2)
C9—C8	1.402 (2)	C30—H30A	0.9700
C9—C10	1.366 (2)	C30—H30B	0.9700
C10—C11	1.504 (2)	C31—H31A	0.9700
C11—H11A	0.9700	C31—H31B	0.9700
C11—H11B	0.9700	C32—C31	1.536 (3)
C13—C12	1.406 (2)	C32—C33	1.533 (2)
C13—C14	1.381 (2)	C32—H32A	0.9700
C13—H13	0.9300	C32—H32B	0.9700
C14—C17	1.506 (2)	C33—H33A	0.9700
C15—C14	1.395 (2)	C33—H33B	0.9700
N1—P1—O1	110.67 (7)	N6—C18—H18A	111.3
N3—P1—O1	105.79 (6)	N6—C18—H18B	111.3
N3—P1—N1	118.29 (7)	C19—C18—H18A	111.3
O1—P1—N4	99.48 (6)	C19—C18—H18B	111.3
N1—P1—N4	109.64 (7)	H18A—C18—H18B	109.2
N3—P1—N4	111.27 (7)	C18—C19—H19A	111.0
N1—P2—N6	112.35 (7)	C18—C19—H19B	111.0
N1—P2—N7	105.29 (7)	C20—C19—C18	103.98 (15)
N2—P2—N1	116.01 (7)	C20—C19—H19A	111.0
N2—P2—N6	105.52 (7)	C20—C19—H19B	111.0
N2—P2—N7	115.07 (7)	H19A—C19—H19B	109.0
N7—P2—N6	101.83 (7)	C19—C20—C21	105.42 (15)
N2—P3—N3	115.10 (7)	C19—C20—H20A	110.7
N2—P3—N8	115.01 (7)	C19—C20—H20B	110.7
N2—P3—N9	106.61 (7)	C21—C20—H20A	110.7
N3—P3—N8	105.41 (7)	C21—C20—H20B	110.7
N3—P3—N9	112.55 (7)	H20A—C20—H20B	108.8
N8—P3—N9	101.46 (7)	N6—C21—C20	104.84 (14)
C9—O1—P1	119.89 (9)	N6—C21—H21A	110.8
P1—N1—P2	120.66 (8)	N6—C21—H21B	110.8
P2—N2—P3	123.76 (8)	C20—C21—H21A	110.8
P1—N3—P3	121.24 (8)	C20—C21—H21B	110.8
C11—N4—P1	122.37 (10)	H21A—C21—H21B	108.9
C12—N4—P1	121.97 (10)	N7—C22—C23	102.68 (13)
C12—N4—C11	115.65 (12)	N7—C22—H22A	111.2
C12—N5—C16	117.13 (14)	N7—C22—H22B	111.2
C18—N6—P2	123.16 (11)	C23—C22—H22A	111.2
C18—N6—C21	109.75 (13)	C23—C22—H22B	111.2
C21—N6—P2	119.56 (11)	H22A—C22—H22B	109.1
C22—N7—P2	126.69 (11)	C22—C23—C24	103.09 (14)
C22—N7—C25	110.66 (13)	C22—C23—H23A	111.1
C25—N7—P2	122.60 (11)	C22—C23—H23B	111.1
C26—N8—P3	122.62 (11)	C24—C23—H23A	111.1
C26—N8—C29	110.42 (12)	C24—C23—H23B	111.1
C29—N8—P3	121.92 (10)	H23A—C23—H23B	109.1
C30—N9—P3	117.42 (10)	C23—C24—C25	104.67 (13)
C33—N9—P3	118.11 (10)	C23—C24—H24A	110.8
C33—N9—C30	106.12 (12)	C23—C24—H24B	110.8
C2—C1—C6	118.33 (14)	C25—C24—H24A	110.8
C2—C1—C10	122.78 (14)	C25—C24—H24B	110.8
C6—C1—C10	118.89 (14)	H24A—C24—H24B	108.9
C1—C2—H2	119.5	N7—C25—C24	104.50 (13)
C3—C2—C1	120.99 (15)	N7—C25—H25A	110.9
C3—C2—H2	119.5	N7—C25—H25B	110.9
C2—C3—C4	120.48 (16)	C24—C25—H25A	110.9
C2—C3—H3	119.8	C24—C25—H25B	110.9
C4—C3—H3	119.8	H25A—C25—H25B	108.9
C5—C4—C3	120.04 (15)	N8—C26—C27	102.75 (13)
C5—C4—H4	120.0	N8—C26—H26A	111.2
C3—C4—H4	120.0	N8—C26—H26B	111.2
C4—C5—C6	121.26 (16)	C27—C26—H26A	111.2
C4—C5—H5	119.4	C27—C26—H26B	111.2
C6—C5—H5	119.4	H26A—C26—H26B	109.1
C7—C6—C1	119.51 (15)	C26—C27—C28	102.77 (13)
C7—C6—C5	121.58 (15)	C26—C27—H27A	111.2
C5—C6—C1	118.89 (15)	C26—C27—H27B	111.2
C6—C7—H7	119.5	C28—C27—H27A	111.2
C8—C7—C6	121.07 (15)	C28—C27—H27B	111.2
C8—C7—H7	119.5	H27A—C27—H27B	109.1
C7—C8—C9	118.64 (15)	C27—C28—C29	103.16 (13)
C7—C8—H8	120.7	C27—C28—H28A	111.1
C9—C8—H8	120.7	C27—C28—H28B	111.1
O1—C9—C8	117.84 (14)	C29—C28—H28A	111.1
C10—C9—O1	118.51 (14)	C29—C28—H28B	111.1
C10—C9—C8	123.59 (15)	H28A—C28—H28B	109.1
C1—C10—C11	122.09 (13)	N8—C29—C28	104.14 (13)
C9—C10—C1	118.30 (14)	N8—C29—H29A	110.9
C9—C10—C11	119.55 (14)	N8—C29—H29B	110.9
N4—C11—C10	113.62 (12)	C28—C29—H29A	110.9
N4—C11—H11A	108.8	C28—C29—H29B	110.9
N4—C11—H11B	108.8	H29A—C29—H29B	108.9
C10—C11—H11A	108.8	N9—C30—C31	103.53 (13)
C10—C11—H11B	108.8	N9—C30—H30A	111.1
H11A—C11—H11B	107.7	N9—C30—H30B	111.1
N4—C12—C13	121.86 (13)	C31—C30—H30A	111.1
N5—C12—N4	115.69 (13)	C31—C30—H30B	111.1
N5—C12—C13	122.45 (14)	H30A—C30—H30B	109.0
C12—C13—H13	120.3	C30—C31—C32	105.54 (14)
C14—C13—C12	119.45 (14)	C30—C31—H31A	110.6
C14—C13—H13	120.3	C30—C31—H31B	110.6
C13—C14—C15	118.09 (15)	C32—C31—H31A	110.6
C13—C14—C17	121.28 (15)	C32—C31—H31B	110.6
C15—C14—C17	120.60 (15)	H31A—C31—H31B	108.8
C14—C15—H15	120.8	C31—C32—H32A	110.6
C16—C15—C14	118.41 (15)	C31—C32—H32B	110.6
C16—C15—H15	120.8	C33—C32—C31	105.59 (13)
N5—C16—C15	124.42 (15)	C33—C32—H32A	110.6
N5—C16—H16	117.8	C33—C32—H32B	110.6
C15—C16—H16	117.8	H32A—C32—H32B	108.8
C14—C17—H17A	109.5	N9—C33—C32	103.77 (13)
C14—C17—H17B	109.5	N9—C33—H33A	111.0
C14—C17—H17C	109.5	N9—C33—H33B	111.0
H17A—C17—H17B	109.5	C32—C33—H33A	111.0
H17A—C17—H17C	109.5	C32—C33—H33B	111.0
H17B—C17—H17C	109.5	H33A—C33—H33B	109.0
N6—C18—C19	102.41 (14)
N1—P1—O1—C9	66.13 (12)	P2—N6—C18—C19	−179.54 (12)
N3—P1—O1—C9	−164.59 (11)	C21—N6—C18—C19	31.07 (17)
N4—P1—O1—C9	−49.16 (12)	P2—N6—C21—C20	−163.38 (12)
O1—P1—N1—P2	101.22 (9)	C18—N6—C21—C20	−12.73 (18)
N3—P1—N1—P2	−21.01 (13)	P2—N7—C22—C23	−154.25 (13)
N4—P1—N1—P2	−150.02 (9)	C25—N7—C22—C23	28.39 (18)
O1—P1—N3—P3	−102.47 (9)	P2—N7—C25—C24	175.08 (12)
N1—P1—N3—P3	22.19 (13)	C22—N7—C25—C24	−7.43 (18)
N4—P1—N3—P3	150.44 (8)	P3—N8—C26—C27	176.80 (11)
O1—P1—N4—C11	11.22 (13)	C29—N8—C26—C27	21.54 (17)
O1—P1—N4—C12	−167.31 (12)	P3—N8—C29—C28	−152.11 (12)
N1—P1—N4—C11	−104.85 (13)	C26—N8—C29—C28	3.36 (17)
N1—P1—N4—C12	76.62 (13)	P3—N9—C30—C31	−173.12 (11)
N3—P1—N4—C11	122.38 (12)	C33—N9—C30—C31	−38.50 (16)
N3—P1—N4—C12	−56.14 (14)	P3—N9—C33—C32	172.79 (11)
N2—P2—N1—P1	16.28 (12)	C30—N9—C33—C32	38.53 (16)
N6—P2—N1—P1	137.78 (9)	C6—C1—C2—C3	−0.7 (2)
N7—P2—N1—P1	−112.21 (10)	C10—C1—C2—C3	178.79 (15)
N1—P2—N2—P3	−13.23 (13)	C2—C1—C6—C5	0.5 (2)
N6—P2—N2—P3	−138.30 (10)	C2—C1—C6—C7	179.07 (15)
N7—P2—N2—P3	110.29 (10)	C10—C1—C6—C5	−179.04 (14)
N1—P2—N6—C18	−93.15 (14)	C10—C1—C6—C7	−0.4 (2)
N1—P2—N6—C21	53.41 (14)	C2—C1—C10—C9	−179.34 (14)
N2—P2—N6—C18	34.17 (14)	C2—C1—C10—C11	−2.3 (2)
N2—P2—N6—C21	−179.27 (12)	C6—C1—C10—C9	0.1 (2)
N7—P2—N6—C18	154.67 (13)	C6—C1—C10—C11	177.20 (14)
N7—P2—N6—C21	−58.77 (13)	C1—C2—C3—C4	0.1 (2)
N1—P2—N7—C22	10.18 (16)	C2—C3—C4—C5	0.7 (2)
N1—P2—N7—C25	−172.75 (13)	C3—C4—C5—C6	−0.9 (3)
N2—P2—N7—C22	−118.86 (14)	C1—C6—C5—C4	0.3 (2)
N2—P2—N7—C25	58.22 (15)	C7—C6—C5—C4	−178.25 (16)
N6—P2—N7—C22	127.58 (14)	C1—C6—C7—C8	0.6 (2)
N6—P2—N7—C25	−55.35 (14)	C5—C6—C7—C8	179.21 (16)
N3—P3—N2—P2	14.06 (13)	C6—C7—C8—C9	−0.5 (3)
N8—P3—N2—P2	136.91 (9)	O1—C9—C8—C7	−176.89 (15)
N9—P3—N2—P2	−111.50 (10)	C10—C9—C8—C7	0.2 (3)
N2—P3—N3—P1	−18.27 (12)	O1—C9—C10—C1	177.07 (13)
N8—P3—N3—P1	−146.11 (9)	O1—C9—C10—C11	−0.1 (2)
N9—P3—N3—P1	104.15 (10)	C8—C9—C10—C1	0.0 (2)
N2—P3—N8—C26	−90.19 (14)	C8—C9—C10—C11	−177.17 (15)
N2—P3—N8—C29	62.30 (14)	C1—C10—C11—N4	147.90 (14)
N3—P3—N8—C26	37.71 (14)	C9—C10—C11—N4	−35.1 (2)
N3—P3—N8—C29	−169.80 (12)	C14—C13—C12—N4	−177.42 (14)
N9—P3—N8—C26	155.21 (13)	C14—C13—C12—N5	1.6 (2)
N9—P3—N8—C29	−52.31 (13)	C12—C13—C14—C15	0.8 (2)
N2—P3—N9—C30	177.45 (11)	C12—C13—C14—C17	−177.17 (15)
N2—P3—N9—C33	48.27 (13)	C16—C15—C14—C13	−2.4 (2)
N3—P3—N9—C30	50.35 (13)	C16—C15—C14—C17	175.60 (16)
N3—P3—N9—C33	−78.82 (13)	C14—C15—C16—N5	1.8 (3)
N8—P3—N9—C30	−61.84 (12)	N6—C18—C19—C20	−36.92 (19)
N8—P3—N9—C33	168.98 (11)	C21—C20—C19—C18	29.8 (2)
P1—O1—C9—C8	−134.76 (13)	N6—C21—C20—C19	−11.1 (2)
P1—O1—C9—C10	47.98 (18)	N7—C22—C23—C24	−37.58 (18)
P1—N4—C11—C10	25.90 (18)	C22—C23—C24—C25	33.58 (18)
C12—N4—C11—C10	−155.48 (13)	N7—C25—C24—C23	−16.68 (18)
P1—N4—C12—N5	165.83 (11)	N8—C26—C27—C28	−37.69 (16)
P1—N4—C12—C13	−15.1 (2)	C26—C27—C28—C29	40.19 (17)
C11—N4—C12—N5	−12.79 (19)	N8—C29—C28—C27	−26.81 (17)
C11—N4—C12—C13	166.32 (14)	N9—C30—C31—C32	22.81 (17)
C16—N5—C12—N4	176.79 (14)	C33—C32—C31—C30	−0.03 (18)
C16—N5—C12—C13	−2.3 (2)	C31—C32—C33—N9	−22.92 (17)
C12—N5—C16—C15	0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O1i	0.96	2.47	3.372 (2)	156
C24—H24B···Cg1ii	0.97	2.74	3.624 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O1i	0.96	2.47	3.372 (2)	156
C24—H24B⋯Cg1ii	0.97	2.74	3.624 (2)	152

Symmetry codes: (i) ; (ii) .