1,1',4,5-Tetra-hydro-tri-spiro-[1,3,2-di-aza-phosphole-2,2'-[1,3,5,2,4,6]tri-aza-triphosphinine-4',6''-dibenzo[d,f][1,3,2]dioxaphosphepine-6',6'''-dibenzo[d,f][1,3,2]dioxaphosphepine] acetone monosolvate.

The title compound, C26H22N5O4P3·C3H6O, has been achieved in a two-step synthesis that does not require chromatography. This mol-ecule contains a seven-membered spiro-cyclic ring at two P-atom positions and a five-membered ring containing new P-N bonds at the other P-atom position. Endocyclic torsion angles about the central biphenyl C-C bonds are -41.5 (3) and -44.4 (3)°, and P-N bonds of the central P3N3 ring are within the range 1.5665 (17)-1.6171 (17) Å, while the P-O distances are in the range 1.5940 (14)-1.6041 (14) Å. One N-H group makes an inter-molecular N-H⋯N hydrogen bond, forming centrosymmetric dimers, while the other N-H group makes an N-H⋯O hydrogen bond to the acetone solvent mol-ecule. The crystal was a two-component non-merohedral twin with ratio 0.811/0.189.

Related literature

For phosphazene-based flame retardants, see: Bakos et al. (1982 ▶); Drews & Barker (1985 ▶). For related structures, bond angles and lengths, see: Allcock (1972 ▶); Ciftci et al. (2013 ▶). For the geometry of phosphazene rings, see: Olthof (1969 ▶); Barclay et al. (2002 ▶). For the synthesis, see: Allen (1991 ▶); Carriedo et al. (1996 ▶). For related structures, see: Chandrasekhar et al. (2007 ▶; 2011 ▶; 2012 ▶); Harmjanz et al. (2004 ▶). For graph-set analysis, see: Etter (1990 ▶). For ring asymmetry parameters, see: Duax et al. (1976 ▶).

Experimental

Crystal data

C26H22N5O4P3·C3H6O

M = 619.47

Monoclinic,

a = 9.4901 (9) Å

b = 22.9466 (19) Å

c = 13.1776 (13) Å

β = 97.978 (6)°

V = 2841.9 (5) Å3

Z = 4

Cu Kα radiation

μ = 2.34 mm−1

T = 100 K

0.19 × 0.12 × 0.03 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: multi-scan (TWINABS; Sheldrick, 2004 ▶) T min = 0.664, T max = 0.933

33208 measured reflections

5065 independent reflections

4276 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.08

5065 reflections

387 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813023830/jj2173sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023830/jj2173Isup2.hkl

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

C26H22N5O4P3·C3H6O	F(000) = 1288
Mr = 619.47	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3314 reflections
a = 9.4901 (9) Å	θ = 3.9–67.8°
b = 22.9466 (19) Å	µ = 2.34 mm−1
c = 13.1776 (13) Å	T = 100 K
β = 97.978 (6)°	Plate, colorless
V = 2841.9 (5) Å3	0.19 × 0.12 × 0.03 mm
Z = 4

Bruker Kappa APEXII DUO CCD diffractometer	5065 independent reflections
Radiation source: IµS microfocus	4276 reflections with I > 2σ(I)
QUAZAR multilayer optics monochromator	Rint = 0.051
φ and ω scans	θmax = 68.7°, θmin = 3.9°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2004)	h = −11→11
Tmin = 0.664, Tmax = 0.933	k = 0→27
33208 measured reflections	l = 0→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.7869P] where P = (Fo2 + 2Fc2)/3
5065 reflections	(Δ/σ)max = 0.001
387 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. The sample was a multiple crystal ("twin") with two components. The second domain was rotated from first domain by 2.6 degrees about reciprocal axis -0.141 1.000 0.976 and real axis -0.085 0.341 1.000The twin law to convert hkl from first to this domain (SHELXL TWIN matrix): 1.002 - 0.016 0.017, 0.096 0.999 0.015, -0.032 - 0.001 0.996

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, using a TWIN4 hkl file prepared by TWINABS (Sheldrick, 2004).

	x	y	z	Uiso*/Ueq
P1	0.86867 (5)	0.57153 (2)	0.27605 (4)	0.01501 (13)
P2	0.70274 (5)	0.47853 (2)	0.30698 (4)	0.01500 (13)
P3	0.79507 (5)	0.55177 (2)	0.47261 (4)	0.01498 (13)
O1	1.02561 (15)	0.56625 (6)	0.24629 (11)	0.0169 (3)
O2	0.80895 (14)	0.62781 (6)	0.21219 (11)	0.0171 (3)
O3	0.77860 (14)	0.41639 (6)	0.30107 (11)	0.0165 (3)
O4	0.54174 (14)	0.46339 (6)	0.26346 (11)	0.0174 (3)
N1	0.77084 (18)	0.51945 (7)	0.22950 (13)	0.0173 (4)
N2	0.69897 (18)	0.49976 (7)	0.41955 (13)	0.0178 (4)
N3	0.89141 (18)	0.58162 (7)	0.39485 (13)	0.0172 (4)
N4	0.70206 (19)	0.59910 (8)	0.52986 (14)	0.0190 (4)
H4N	0.659 (3)	0.6247 (11)	0.4945 (19)	0.023*
N5	0.89724 (19)	0.53234 (8)	0.57900 (13)	0.0182 (4)
H5N	0.921 (3)	0.4976 (11)	0.5831 (19)	0.022*
C1	1.0620 (2)	0.58150 (9)	0.14985 (16)	0.0175 (4)
C2	1.1120 (2)	0.53795 (9)	0.09149 (16)	0.0195 (4)
H2	1.1120	0.4985	0.1134	0.023*
C3	1.1619 (2)	0.55245 (9)	0.00081 (17)	0.0231 (5)
H3	1.1962	0.5228	−0.0399	0.028*
C4	1.1620 (2)	0.61020 (10)	−0.03067 (16)	0.0233 (5)
H4	1.1973	0.6201	−0.0925	0.028*
C5	1.1105 (2)	0.65351 (9)	0.02810 (16)	0.0205 (4)
H5	1.1096	0.6928	0.0054	0.025*
C6	1.0600 (2)	0.64004 (9)	0.12034 (15)	0.0170 (4)
C7	1.0101 (2)	0.68643 (8)	0.18533 (15)	0.0174 (4)
C8	1.0836 (2)	0.73950 (9)	0.20275 (16)	0.0203 (4)
H8	1.1679	0.7460	0.1730	0.024*
C9	1.0346 (2)	0.78235 (9)	0.26264 (16)	0.0225 (5)
H9	1.0854	0.8180	0.2735	0.027*
C10	0.9119 (2)	0.77390 (9)	0.30718 (16)	0.0218 (4)
H10	0.8794	0.8035	0.3486	0.026*
C11	0.8369 (2)	0.72215 (9)	0.29101 (16)	0.0205 (4)
H11	0.7523	0.7159	0.3206	0.025*
C12	0.8877 (2)	0.67975 (8)	0.23097 (16)	0.0175 (4)
C13	0.7274 (2)	0.37086 (8)	0.35739 (16)	0.0170 (4)
C14	0.8068 (2)	0.35465 (9)	0.44930 (16)	0.0207 (4)
H14	0.8913	0.3751	0.4752	0.025*
C15	0.7602 (3)	0.30792 (9)	0.50272 (17)	0.0265 (5)
H15	0.8124	0.2964	0.5663	0.032*
C16	0.6377 (2)	0.27796 (9)	0.46347 (18)	0.0265 (5)
H16	0.6068	0.2458	0.5000	0.032*
C17	0.5602 (2)	0.29493 (9)	0.37092 (18)	0.0234 (5)
H17	0.4765	0.2741	0.3446	0.028*
C18	0.6038 (2)	0.34235 (8)	0.31581 (16)	0.0182 (4)
C19	0.5226 (2)	0.36114 (9)	0.21647 (16)	0.0182 (4)
C20	0.4629 (2)	0.32016 (9)	0.14425 (18)	0.0246 (5)
H20	0.4762	0.2798	0.1586	0.029*
C21	0.3846 (2)	0.33719 (11)	0.05215 (19)	0.0296 (5)
H21	0.3440	0.3086	0.0047	0.036*
C22	0.3657 (2)	0.39597 (11)	0.02949 (18)	0.0291 (5)
H22	0.3130	0.4077	−0.0338	0.035*
C23	0.4239 (2)	0.43759 (10)	0.09950 (17)	0.0237 (5)
H23	0.4115	0.4779	0.0845	0.028*
C24	0.5001 (2)	0.41980 (9)	0.19118 (16)	0.0178 (4)
C25	0.7808 (2)	0.61684 (9)	0.62821 (16)	0.0233 (5)
H25A	0.7156	0.6317	0.6748	0.028*
H25B	0.8514	0.6475	0.6188	0.028*
C26	0.8542 (2)	0.56094 (9)	0.67000 (16)	0.0213 (4)
H26A	0.9382	0.5698	0.7211	0.026*
H26B	0.7880	0.5360	0.7024	0.026*
O5	0.53486 (16)	0.66469 (7)	0.35745 (12)	0.0258 (3)
C27	0.4623 (2)	0.62727 (9)	0.30959 (17)	0.0220 (5)
C28	0.3829 (2)	0.58239 (9)	0.36180 (18)	0.0255 (5)
H28A	0.4119	0.5846	0.4360	0.038*
H28B	0.4045	0.5435	0.3373	0.038*
H28C	0.2805	0.5897	0.3462	0.038*
C29	0.4499 (3)	0.62433 (11)	0.19530 (18)	0.0307 (5)
H29A	0.4922	0.6594	0.1695	0.046*
H29B	0.3493	0.6219	0.1661	0.046*
H29C	0.5002	0.5898	0.1754	0.046*

	U11	U22	U33	U12	U13	U23
P1	0.0158 (3)	0.0150 (2)	0.0145 (3)	−0.00015 (19)	0.00280 (19)	0.00056 (18)
P2	0.0159 (3)	0.0140 (2)	0.0153 (3)	−0.00058 (19)	0.00309 (19)	−0.00092 (18)
P3	0.0156 (3)	0.0156 (2)	0.0139 (3)	0.00053 (19)	0.00267 (19)	−0.00072 (18)
O1	0.0168 (7)	0.0184 (7)	0.0161 (7)	0.0007 (5)	0.0041 (6)	0.0038 (5)
O2	0.0156 (7)	0.0159 (7)	0.0194 (7)	−0.0013 (5)	0.0007 (6)	0.0012 (5)
O3	0.0165 (7)	0.0152 (6)	0.0183 (7)	−0.0007 (5)	0.0041 (5)	−0.0009 (5)
O4	0.0157 (7)	0.0159 (6)	0.0206 (8)	0.0000 (5)	0.0024 (6)	−0.0040 (6)
N1	0.0196 (9)	0.0177 (8)	0.0151 (9)	−0.0020 (7)	0.0042 (7)	−0.0015 (6)
N2	0.0195 (9)	0.0173 (8)	0.0173 (9)	−0.0020 (7)	0.0051 (7)	0.0005 (7)
N3	0.0181 (9)	0.0174 (8)	0.0158 (9)	−0.0023 (7)	0.0016 (7)	−0.0005 (7)
N4	0.0203 (9)	0.0193 (8)	0.0176 (9)	0.0041 (7)	0.0030 (7)	−0.0017 (7)
N5	0.0204 (9)	0.0187 (8)	0.0154 (9)	0.0028 (7)	0.0019 (7)	0.0007 (7)
C1	0.0141 (10)	0.0234 (10)	0.0151 (10)	−0.0017 (8)	0.0029 (8)	0.0003 (8)
C2	0.0189 (10)	0.0177 (9)	0.0215 (11)	−0.0003 (8)	0.0013 (8)	−0.0007 (8)
C3	0.0216 (11)	0.0263 (11)	0.0212 (11)	0.0020 (9)	0.0025 (9)	−0.0039 (9)
C4	0.0239 (11)	0.0307 (11)	0.0160 (11)	−0.0022 (9)	0.0051 (9)	0.0007 (9)
C5	0.0215 (11)	0.0203 (10)	0.0198 (11)	−0.0004 (8)	0.0031 (8)	0.0031 (8)
C6	0.0151 (10)	0.0193 (10)	0.0167 (10)	−0.0017 (8)	0.0025 (8)	−0.0015 (8)
C7	0.0191 (10)	0.0181 (9)	0.0148 (10)	0.0008 (8)	0.0016 (8)	0.0033 (8)
C8	0.0225 (11)	0.0207 (10)	0.0184 (11)	−0.0024 (8)	0.0054 (8)	0.0034 (8)
C9	0.0307 (12)	0.0159 (9)	0.0209 (11)	−0.0046 (9)	0.0031 (9)	0.0009 (8)
C10	0.0286 (11)	0.0171 (10)	0.0201 (11)	0.0019 (9)	0.0051 (9)	−0.0019 (8)
C11	0.0199 (10)	0.0204 (10)	0.0212 (11)	0.0029 (8)	0.0036 (8)	0.0038 (8)
C12	0.0198 (10)	0.0132 (9)	0.0186 (10)	−0.0013 (8)	−0.0004 (8)	0.0023 (7)
C13	0.0207 (10)	0.0139 (9)	0.0182 (10)	0.0005 (8)	0.0091 (8)	−0.0011 (8)
C14	0.0228 (11)	0.0184 (9)	0.0213 (11)	0.0052 (8)	0.0044 (9)	−0.0030 (8)
C15	0.0379 (13)	0.0220 (10)	0.0208 (11)	0.0116 (10)	0.0087 (10)	0.0028 (9)
C16	0.0331 (13)	0.0194 (10)	0.0308 (13)	0.0044 (9)	0.0181 (10)	0.0044 (9)
C17	0.0236 (11)	0.0172 (10)	0.0316 (13)	0.0004 (8)	0.0113 (9)	−0.0014 (9)
C18	0.0185 (10)	0.0152 (9)	0.0227 (11)	0.0021 (8)	0.0092 (8)	−0.0027 (8)
C19	0.0148 (10)	0.0212 (10)	0.0202 (11)	−0.0021 (8)	0.0073 (8)	−0.0031 (8)
C20	0.0216 (11)	0.0228 (11)	0.0307 (13)	−0.0033 (9)	0.0086 (9)	−0.0087 (9)
C21	0.0229 (11)	0.0378 (13)	0.0276 (13)	−0.0032 (10)	0.0015 (9)	−0.0167 (10)
C22	0.0231 (12)	0.0412 (13)	0.0218 (12)	0.0024 (10)	−0.0015 (9)	−0.0063 (10)
C23	0.0209 (11)	0.0257 (11)	0.0241 (12)	0.0025 (9)	0.0019 (9)	−0.0006 (9)
C24	0.0138 (10)	0.0202 (10)	0.0196 (11)	−0.0008 (8)	0.0038 (8)	−0.0046 (8)
C25	0.0234 (11)	0.0275 (11)	0.0188 (11)	0.0003 (9)	0.0023 (9)	−0.0057 (9)
C26	0.0213 (11)	0.0268 (10)	0.0159 (11)	−0.0005 (9)	0.0029 (8)	−0.0013 (8)
O5	0.0236 (8)	0.0247 (8)	0.0291 (9)	−0.0022 (6)	0.0034 (7)	−0.0016 (6)
C27	0.0162 (10)	0.0234 (10)	0.0268 (12)	0.0065 (9)	0.0039 (9)	−0.0008 (9)
C28	0.0210 (11)	0.0245 (11)	0.0319 (13)	0.0012 (9)	0.0069 (9)	−0.0014 (9)
C29	0.0257 (12)	0.0403 (13)	0.0255 (13)	−0.0010 (10)	0.0017 (10)	0.0027 (10)

P1—N3	1.5675 (17)	C10—H10	0.9500
P1—N1	1.5837 (17)	C11—C12	1.382 (3)
P1—O1	1.5965 (14)	C11—H11	0.9500
P1—O2	1.6016 (14)	C13—C14	1.385 (3)
P2—N2	1.5665 (17)	C13—C18	1.388 (3)
P2—N1	1.5890 (17)	C14—C15	1.388 (3)
P2—O4	1.5940 (14)	C14—H14	0.9500
P2—O3	1.6041 (14)	C15—C16	1.387 (3)
P3—N2	1.6024 (17)	C15—H15	0.9500
P3—N3	1.6171 (17)	C16—C17	1.390 (3)
P3—N4	1.6471 (17)	C16—H16	0.9500
P3—N5	1.6514 (18)	C17—C18	1.402 (3)
O1—C1	1.407 (2)	C17—H17	0.9500
O2—C12	1.410 (2)	C18—C19	1.488 (3)
O3—C13	1.407 (2)	C19—C24	1.396 (3)
O4—C24	1.400 (2)	C19—C20	1.401 (3)
N4—C25	1.461 (3)	C20—C21	1.388 (3)
N4—H4N	0.82 (3)	C20—H20	0.9500
N5—C26	1.473 (3)	C21—C22	1.388 (4)
N5—H5N	0.83 (3)	C21—H21	0.9500
C1—C2	1.384 (3)	C22—C23	1.388 (3)
C1—C6	1.398 (3)	C22—H22	0.9500
C2—C3	1.386 (3)	C23—C24	1.381 (3)
C2—H2	0.9500	C23—H23	0.9500
C3—C4	1.389 (3)	C25—C26	1.526 (3)
C3—H3	0.9500	C25—H25A	0.9900
C4—C5	1.390 (3)	C25—H25B	0.9900
C4—H4	0.9500	C26—H26A	0.9900
C5—C6	1.402 (3)	C26—H26B	0.9900
C5—H5	0.9500	O5—C27	1.220 (3)
C6—C7	1.484 (3)	C27—C29	1.496 (3)
C7—C12	1.389 (3)	C27—C28	1.498 (3)
C7—C8	1.406 (3)	C28—H28A	0.9800
C8—C9	1.381 (3)	C28—H28B	0.9800
C8—H8	0.9500	C28—H28C	0.9800
C9—C10	1.388 (3)	C29—H29A	0.9800
C9—H9	0.9500	C29—H29B	0.9800
C10—C11	1.386 (3)	C29—H29C	0.9800
N3—P1—N1	119.36 (9)	C11—C12—O2	118.47 (18)
N3—P1—O1	104.64 (8)	C7—C12—O2	118.17 (17)
N1—P1—O1	111.37 (8)	C14—C13—C18	123.09 (19)
N3—P1—O2	113.28 (8)	C14—C13—O3	118.37 (18)
N1—P1—O2	105.03 (8)	C18—C13—O3	118.46 (18)
O1—P1—O2	101.90 (7)	C13—C14—C15	118.6 (2)
N2—P2—N1	119.30 (9)	C13—C14—H14	120.7
N2—P2—O4	105.18 (8)	C15—C14—H14	120.7
N1—P2—O4	110.65 (8)	C16—C15—C14	120.2 (2)
N2—P2—O3	113.07 (9)	C16—C15—H15	119.9
N1—P2—O3	105.59 (8)	C14—C15—H15	119.9
O4—P2—O3	101.71 (7)	C15—C16—C17	120.2 (2)
N2—P3—N3	112.12 (9)	C15—C16—H16	119.9
N2—P3—N4	112.47 (9)	C17—C16—H16	119.9
N3—P3—N4	113.39 (9)	C16—C17—C18	120.9 (2)
N2—P3—N5	113.64 (9)	C16—C17—H17	119.6
N3—P3—N5	109.59 (9)	C18—C17—H17	119.6
N4—P3—N5	94.47 (9)	C13—C18—C17	117.1 (2)
C1—O1—P1	123.88 (13)	C13—C18—C19	121.14 (18)
C12—O2—P1	116.68 (12)	C17—C18—C19	121.76 (19)
C13—O3—P2	116.39 (12)	C24—C19—C20	116.8 (2)
C24—O4—P2	124.52 (12)	C24—C19—C18	122.21 (18)
P1—N1—P2	117.77 (11)	C20—C19—C18	120.98 (19)
P2—N2—P3	123.95 (11)	C21—C20—C19	121.5 (2)
P1—N3—P3	123.96 (11)	C21—C20—H20	119.3
C25—N4—P3	110.45 (14)	C19—C20—H20	119.3
C25—N4—H4N	117.0 (17)	C22—C21—C20	119.9 (2)
P3—N4—H4N	117.8 (18)	C22—C21—H21	120.0
C26—N5—P3	111.99 (14)	C20—C21—H21	120.0
C26—N5—H5N	118.6 (17)	C21—C22—C23	119.9 (2)
P3—N5—H5N	115.9 (17)	C21—C22—H22	120.1
C2—C1—C6	122.12 (19)	C23—C22—H22	120.1
C2—C1—O1	117.93 (18)	C24—C23—C22	119.3 (2)
C6—C1—O1	119.65 (18)	C24—C23—H23	120.3
C1—C2—C3	119.36 (19)	C22—C23—H23	120.3
C1—C2—H2	120.3	C23—C24—C19	122.56 (19)
C3—C2—H2	120.3	C23—C24—O4	116.64 (18)
C2—C3—C4	120.1 (2)	C19—C24—O4	120.46 (18)
C2—C3—H3	120.0	N4—C25—C26	103.74 (17)
C4—C3—H3	120.0	N4—C25—H25A	111.0
C3—C4—C5	120.1 (2)	C26—C25—H25A	111.0
C3—C4—H4	120.0	N4—C25—H25B	111.0
C5—C4—H4	120.0	C26—C25—H25B	111.0
C4—C5—C6	120.97 (19)	H25A—C25—H25B	109.0
C4—C5—H5	119.5	N5—C26—C25	104.18 (17)
C6—C5—H5	119.5	N5—C26—H26A	110.9
C1—C6—C5	117.38 (19)	C25—C26—H26A	110.9
C1—C6—C7	121.47 (18)	N5—C26—H26B	110.9
C5—C6—C7	121.13 (18)	C25—C26—H26B	110.9
C12—C7—C8	116.76 (18)	H26A—C26—H26B	108.9
C12—C7—C6	121.56 (18)	O5—C27—C29	120.8 (2)
C8—C7—C6	121.68 (18)	O5—C27—C28	122.0 (2)
C9—C8—C7	120.7 (2)	C29—C27—C28	117.21 (19)
C9—C8—H8	119.6	C27—C28—H28A	109.5
C7—C8—H8	119.6	C27—C28—H28B	109.5
C8—C9—C10	120.73 (19)	H28A—C28—H28B	109.5
C8—C9—H9	119.6	C27—C28—H28C	109.5
C10—C9—H9	119.6	H28A—C28—H28C	109.5
C11—C10—C9	119.85 (19)	H28B—C28—H28C	109.5
C11—C10—H10	120.1	C27—C29—H29A	109.5
C9—C10—H10	120.1	C27—C29—H29B	109.5
C12—C11—C10	118.6 (2)	H29A—C29—H29B	109.5
C12—C11—H11	120.7	C27—C29—H29C	109.5
C10—C11—H11	120.7	H29A—C29—H29C	109.5
C11—C12—C7	123.33 (18)	H29B—C29—H29C	109.5
N3—P1—O1—C1	−151.76 (15)	C5—C6—C7—C12	137.4 (2)
N1—P1—O1—C1	77.97 (16)	C1—C6—C7—C8	136.4 (2)
O2—P1—O1—C1	−33.56 (16)	C5—C6—C7—C8	−41.9 (3)
N3—P1—O2—C12	54.75 (16)	C12—C7—C8—C9	0.0 (3)
N1—P1—O2—C12	−173.32 (14)	C6—C7—C8—C9	179.33 (19)
O1—P1—O2—C12	−57.08 (15)	C7—C8—C9—C10	0.2 (3)
N2—P2—O3—C13	52.84 (16)	C8—C9—C10—C11	−0.4 (3)
N1—P2—O3—C13	−175.00 (13)	C9—C10—C11—C12	0.5 (3)
O4—P2—O3—C13	−59.42 (15)	C10—C11—C12—C7	−0.3 (3)
N2—P2—O4—C24	−148.34 (15)	C10—C11—C12—O2	−178.18 (18)
N1—P2—O4—C24	81.56 (17)	C8—C7—C12—C11	0.1 (3)
O3—P2—O4—C24	−30.24 (17)	C6—C7—C12—C11	−179.23 (19)
N3—P1—N1—P2	−1.48 (16)	C8—C7—C12—O2	177.90 (17)
O1—P1—N1—P2	120.63 (11)	C6—C7—C12—O2	−1.4 (3)
O2—P1—N1—P2	−129.84 (11)	P1—O2—C12—C11	−103.17 (18)
N2—P2—N1—P1	16.39 (16)	P1—O2—C12—C7	78.9 (2)
O4—P2—N1—P1	138.55 (10)	P2—O3—C13—C14	−103.07 (18)
O3—P2—N1—P1	−112.16 (11)	P2—O3—C13—C18	80.20 (19)
N1—P2—N2—P3	−17.32 (17)	C18—C13—C14—C15	−0.4 (3)
O4—P2—N2—P3	−142.15 (12)	O3—C13—C14—C15	−176.97 (17)
O3—P2—N2—P3	107.71 (12)	C13—C14—C15—C16	0.8 (3)
N3—P3—N2—P2	2.48 (16)	C14—C15—C16—C17	−0.6 (3)
N4—P3—N2—P2	131.67 (12)	C15—C16—C17—C18	−0.1 (3)
N5—P3—N2—P2	−122.48 (13)	C14—C13—C18—C17	−0.3 (3)
N1—P1—N3—P3	−14.21 (17)	O3—C13—C18—C17	176.31 (17)
O1—P1—N3—P3	−139.60 (11)	C14—C13—C18—C19	−179.62 (18)
O2—P1—N3—P3	110.26 (12)	O3—C13—C18—C19	−3.0 (3)
N2—P3—N3—P1	13.44 (16)	C16—C17—C18—C13	0.5 (3)
N4—P3—N3—P1	−115.26 (13)	C16—C17—C18—C19	179.83 (19)
N5—P3—N3—P1	140.61 (12)	C13—C18—C19—C24	−41.5 (3)
N2—P3—N4—C25	138.76 (14)	C17—C18—C19—C24	139.2 (2)
N3—P3—N4—C25	−92.72 (16)	C13—C18—C19—C20	139.6 (2)
N5—P3—N4—C25	20.88 (16)	C17—C18—C19—C20	−39.7 (3)
N2—P3—N5—C26	−112.97 (15)	C24—C19—C20—C21	−0.2 (3)
N3—P3—N5—C26	120.73 (15)	C18—C19—C20—C21	178.7 (2)
N4—P3—N5—C26	3.95 (16)	C19—C20—C21—C22	0.8 (3)
P1—O1—C1—C2	−117.03 (18)	C20—C21—C22—C23	−0.7 (4)
P1—O1—C1—C6	69.1 (2)	C21—C22—C23—C24	−0.1 (3)
C6—C1—C2—C3	0.1 (3)	C22—C23—C24—C19	0.7 (3)
O1—C1—C2—C3	−173.67 (18)	C22—C23—C24—O4	−172.71 (19)
C1—C2—C3—C4	0.2 (3)	C20—C19—C24—C23	−0.5 (3)
C2—C3—C4—C5	−0.7 (3)	C18—C19—C24—C23	−179.51 (19)
C3—C4—C5—C6	1.0 (3)	C20—C19—C24—O4	172.62 (18)
C2—C1—C6—C5	0.2 (3)	C18—C19—C24—O4	−6.3 (3)
O1—C1—C6—C5	173.83 (17)	P2—O4—C24—C23	−118.86 (18)
C2—C1—C6—C7	−178.11 (19)	P2—O4—C24—C19	67.6 (2)
O1—C1—C6—C7	−4.5 (3)	P3—N4—C25—C26	−37.8 (2)
C4—C5—C6—C1	−0.7 (3)	P3—N5—C26—C25	−25.7 (2)
C4—C5—C6—C7	177.58 (19)	N4—C25—C26—N5	38.3 (2)
C1—C6—C7—C12	−44.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···O5	0.82 (3)	2.22 (3)	2.991 (2)	158 (2)
N5—H5N···N3i	0.83 (3)	2.53 (3)	3.285 (2)	151 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯O5	0.82 (3)	2.22 (3)	2.991 (2)	158 (2)
N5—H5N⋯N3i	0.83 (3)	2.53 (3)	3.285 (2)	151 (2)

Symmetry code: (i) .