Structural investigations of phosphorus–nitrogen compounds. 5. Relationships between molecular parameters of 2,2-diphenyl-4,6-cis-oxytetra­(ethyl­ene­oxy)-4,6-R2-cyclotriphosphazatrienes (R = Cl, OCH2CF3, OPh, OMe, NHPh, NHBut) and substituent basicity constants

Beşli, S.; Coles, S.J.; Davies, D.B.; Hursthouse, M.B.; Kılıç, A.; Mayer, T.A.; Shaw, R.A.

doi:10.1107/S0108768102018608

Structural investigations of phosphorus–nitrogen compounds. 5. Relationships between molecular parameters of 2,2-diphenyl-4,6-cis-oxytetra(ethyleneoxy)-4,6-R₂-cyclotriphosphazatrienes (R = Cl, OCH₂CF₃, OPh, OMe, NHPh, NHBu^t) and substituent basicity constants

S. Beşli, S. J. Coles, D. B. Davies, M. B. Hursthouse, A. Kılıç, T. A. Mayer and R. A. Shaw

A systematic study of the products of nucleophilic substitution reactions of cis-ansa N₃P₃Ph₂[O(CH₂CH₂O)₄]Cl₂ (3) is reported. These reactions give a number of new structures with the general formula N₃P₃Ph₂[O(CH₂CH₂O)₄]R₂ [where R = OCH₂CF₃ (4), OPh (5), OMe (6), NHPh (7·H₂O), NHBu^t (8)]. A comparison has been made between the sum of the substituent basicity constants, $\textstyle\sum$ α_R, that are obtained in nitrobenzene solution and eight molecular parameters of the N₃P₃ ring [the P—N bond lengths a, b, c; the internal bond angles α, β, γ, δ; and the difference between the bond lengths a and b, Δ(P—N)]. It is found that the systematic changes in the molecular parameters of (3)–(8) are in line with changes in α_R values. This result implies the similarity in relative electron-releasing capacity of substituents R in the solid state and in solution.

Keywords: phosphorus–nitrogen compounds; cyclophosphazenes; substituent basicity constants; molecular parameters.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768102018608/bm0058sup1.cif Contains datablocks 3, 4, 5, 6, 7, 8
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00583sup2.hkl Contains datablock 3
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00584sup3.hkl Contains datablock 4
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00585sup4.hkl Contains datablock 5
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00586sup5.hkl Contains datablock 6
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00587sup6.hkl Contains datablock 7
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768102018608/bm00588sup7.hkl Contains datablock 8
	Portable Document Format (PDF) file https://doi.org/10.1107/S0108768102018608/bm0058sup8.pdf Preparation of the compounds

CCDC references: 201638; 201639; 201640; 201641; 201642; 201643

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998) for (3), (4), (7), (8); DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998) for (5), (6). For all compounds, cell refinement: DENZO & COLLECT; data reduction: DENZO & COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

Figures top

(3) top

Crystal data top

C₂₀H₂₆Cl₂N₃O₅P₃	F(000) = 1144
M_r = 552.25	D_x = 1.462 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 17.618 (4) Å	Cell parameters from 7188 reflections
b = 8.1109 (16) Å	θ = 2.9–27.5°
c = 19.284 (4) Å	µ = 0.49 mm⁻¹
β = 114.44 (3)°	T = 150 K
V = 2508.8 (9) Å³	Block, colourless
Z = 4	0.32 × 0.28 × 0.13 mm

Data collection top

Nonius KappaCCD diffractometer	5657 independent reflections
Radiation source: Nonius FR591 rotating anode	4268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ϕ and ω scans	h = −22→22
Absorption correction: multi-scan SORTAV (Blessing, 1997)	k = −9→10
T_min = 0.860, T_max = 0.939	l = −24→25
17345 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0421P)² + 1.1841P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.002
5657 reflections	Δρ_max = 0.32 e Å⁻³
299 parameters	Δρ_min = −0.46 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0041 (7)

Crystal data top

C₂₀H₂₆Cl₂N₃O₅P₃	V = 2508.8 (9) Å³
M_r = 552.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 17.618 (4) Å	µ = 0.49 mm⁻¹
b = 8.1109 (16) Å	T = 150 K
c = 19.284 (4) Å	0.32 × 0.28 × 0.13 mm
β = 114.44 (3)°

Data collection top

Nonius KappaCCD diffractometer	5657 independent reflections
Absorption correction: multi-scan SORTAV (Blessing, 1997)	4268 reflections with I > 2σ(I)
T_min = 0.860, T_max = 0.939	R_int = 0.045
17345 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.01	Δρ_max = 0.32 e Å⁻³
5657 reflections	Δρ_min = −0.46 e Å⁻³
299 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.34690 (14)	0.3650 (3)	0.08190 (13)	0.0353 (5)
H1A	0.3652	0.3039	0.0471	0.042*
H1B	0.3723	0.4762	0.0906	0.042*
C2	0.25355 (14)	0.3779 (3)	0.04826 (14)	0.0351 (5)
H2A	0.2353	0.4285	0.0855	0.042*
H2B	0.2338	0.4480	0.0021	0.042*
C3	0.13197 (13)	0.2129 (3)	0.00253 (13)	0.0324 (5)
H3A	0.1057	0.2725	−0.0465	0.039*
H3B	0.1146	0.2663	0.0398	0.039*
C4	0.10552 (13)	0.0361 (3)	−0.00783 (12)	0.0314 (5)
H4A	0.0441	0.0287	−0.0355	0.038*
H4B	0.1310	−0.0217	−0.0381	0.038*
C5	0.12177 (14)	−0.2125 (3)	0.06105 (12)	0.0314 (5)
H5A	0.1535	−0.2607	0.0339	0.038*
H5B	0.0622	−0.2408	0.0323	0.038*
C6	0.15258 (14)	−0.2830 (3)	0.13942 (13)	0.0332 (5)
H6A	0.1305	−0.2179	0.1704	0.040*
H6B	0.1328	−0.3980	0.1369	0.040*
C7	0.27381 (15)	−0.3424 (3)	0.24890 (13)	0.0343 (5)
H7A	0.2556	−0.4579	0.2487	0.041*
H7B	0.2535	−0.2762	0.2809	0.041*
C8	0.36667 (14)	−0.3344 (3)	0.28008 (13)	0.0329 (5)
H8A	0.3916	−0.3913	0.3299	0.039*
H8B	0.3865	−0.3892	0.2448	0.039*
C9	0.42545 (13)	−0.1990 (2)	0.05410 (11)	0.0232 (4)
C10	0.45124 (14)	−0.2951 (3)	0.00783 (11)	0.0286 (5)
H10	0.5089	−0.3171	0.0230	0.034*
C11	0.39313 (15)	−0.3588 (3)	−0.06037 (12)	0.0337 (5)
H11	0.4110	−0.4242	−0.0917	0.040*
C12	0.30945 (14)	−0.3269 (3)	−0.08254 (12)	0.0325 (5)
H12	0.2696	−0.3698	−0.1293	0.039*
C13	0.28353 (14)	−0.2326 (3)	−0.03664 (13)	0.0341 (5)
H13	0.2258	−0.2119	−0.0519	0.041*
C14	0.34047 (13)	−0.1682 (3)	0.03104 (12)	0.0306 (5)
H14	0.3219	−0.1030	0.0620	0.037*
C15	0.59947 (13)	−0.1647 (2)	0.15535 (11)	0.0242 (4)
C16	0.64688 (13)	−0.2713 (3)	0.21393 (11)	0.0274 (5)
H16	0.6255	−0.3092	0.2490	0.033*
C17	0.72477 (14)	−0.3224 (3)	0.22145 (13)	0.0340 (5)
H17	0.7569	−0.3946	0.2617	0.041*
C18	0.75587 (14)	−0.2685 (3)	0.17056 (13)	0.0349 (5)
H18	0.8089	−0.3058	0.1752	0.042*
C19	0.71016 (14)	−0.1602 (3)	0.11262 (13)	0.0344 (5)
H19	0.7322	−0.1223	0.0781	0.041*
C20	0.63259 (14)	−0.1077 (3)	0.10513 (12)	0.0295 (5)
H20	0.6016	−0.0325	0.0658	0.035*
N1	0.45554 (11)	0.0985 (2)	0.26501 (10)	0.0286 (4)
N2	0.47795 (11)	−0.1963 (2)	0.20964 (9)	0.0246 (4)
N3	0.48236 (11)	0.0870 (2)	0.13602 (9)	0.0268 (4)
O1	0.37151 (9)	0.27752 (18)	0.15361 (8)	0.0302 (3)
O2	0.21987 (9)	0.21724 (18)	0.02925 (9)	0.0320 (4)
O3	0.13151 (10)	−0.03846 (19)	0.06479 (8)	0.0338 (4)
O4	0.24094 (9)	−0.2794 (2)	0.17365 (8)	0.0332 (4)
O5	0.39105 (9)	−0.16149 (18)	0.28902 (9)	0.0322 (4)
P1	0.45731 (3)	0.18753 (6)	0.19288 (3)	0.02392 (14)
P2	0.46451 (3)	−0.09408 (6)	0.27249 (3)	0.02262 (14)
P3	0.49581 (3)	−0.10982 (6)	0.14295 (3)	0.02192 (14)
Cl1	0.53581 (4)	0.38143 (7)	0.22985 (4)	0.04032 (17)
Cl2	0.56344 (4)	−0.13776 (9)	0.37365 (3)	0.0519 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0336 (13)	0.0305 (13)	0.0424 (13)	0.0002 (10)	0.0162 (11)	0.0135 (10)
C2	0.0325 (12)	0.0246 (12)	0.0456 (13)	0.0024 (10)	0.0135 (11)	0.0101 (10)
C3	0.0240 (11)	0.0332 (13)	0.0419 (12)	0.0045 (9)	0.0156 (10)	0.0057 (10)
C4	0.0276 (11)	0.0338 (13)	0.0337 (11)	0.0016 (10)	0.0137 (10)	0.0013 (9)
C5	0.0312 (12)	0.0272 (12)	0.0397 (12)	−0.0041 (9)	0.0184 (10)	−0.0030 (9)
C6	0.0347 (13)	0.0282 (12)	0.0451 (13)	−0.0030 (10)	0.0250 (11)	0.0012 (10)
C7	0.0440 (14)	0.0302 (12)	0.0380 (12)	−0.0012 (10)	0.0264 (11)	0.0074 (10)
C8	0.0436 (14)	0.0245 (12)	0.0375 (12)	−0.0003 (10)	0.0237 (11)	0.0059 (9)
C9	0.0274 (11)	0.0193 (10)	0.0277 (10)	0.0008 (8)	0.0162 (9)	0.0032 (8)
C10	0.0300 (11)	0.0290 (12)	0.0288 (11)	0.0054 (9)	0.0143 (9)	0.0015 (9)
C11	0.0415 (14)	0.0318 (13)	0.0288 (11)	0.0025 (10)	0.0156 (10)	−0.0048 (9)
C12	0.0351 (13)	0.0281 (12)	0.0297 (11)	−0.0039 (10)	0.0088 (10)	0.0017 (9)
C13	0.0253 (11)	0.0348 (13)	0.0427 (13)	−0.0027 (10)	0.0145 (10)	0.0017 (10)
C14	0.0291 (12)	0.0298 (12)	0.0385 (12)	0.0008 (9)	0.0197 (10)	−0.0011 (10)
C15	0.0274 (11)	0.0213 (11)	0.0260 (10)	−0.0013 (8)	0.0132 (9)	−0.0031 (8)
C16	0.0316 (12)	0.0241 (11)	0.0268 (10)	−0.0011 (9)	0.0124 (9)	−0.0020 (8)
C17	0.0323 (12)	0.0317 (13)	0.0328 (11)	0.0030 (10)	0.0081 (10)	−0.0018 (10)
C18	0.0233 (11)	0.0340 (13)	0.0458 (13)	−0.0006 (10)	0.0128 (10)	−0.0088 (11)
C19	0.0353 (13)	0.0329 (13)	0.0449 (13)	−0.0047 (10)	0.0265 (11)	−0.0053 (10)
C20	0.0324 (12)	0.0269 (12)	0.0336 (11)	−0.0017 (9)	0.0180 (10)	0.0020 (9)
N1	0.0407 (11)	0.0202 (9)	0.0305 (9)	0.0028 (8)	0.0203 (8)	−0.0016 (7)
N2	0.0350 (10)	0.0176 (9)	0.0294 (9)	0.0021 (7)	0.0214 (8)	0.0017 (7)
N3	0.0409 (11)	0.0167 (9)	0.0311 (9)	0.0012 (8)	0.0231 (8)	0.0027 (7)
O1	0.0280 (8)	0.0298 (8)	0.0361 (8)	0.0056 (6)	0.0166 (7)	0.0069 (7)
O2	0.0262 (8)	0.0267 (8)	0.0459 (9)	0.0026 (6)	0.0177 (7)	0.0048 (7)
O3	0.0453 (9)	0.0266 (8)	0.0342 (8)	−0.0009 (7)	0.0212 (7)	−0.0001 (6)
O4	0.0325 (9)	0.0387 (9)	0.0343 (8)	−0.0017 (7)	0.0198 (7)	0.0065 (7)
O5	0.0402 (9)	0.0263 (8)	0.0424 (8)	−0.0044 (7)	0.0296 (7)	−0.0039 (7)
P1	0.0268 (3)	0.0171 (3)	0.0312 (3)	0.0005 (2)	0.0153 (2)	−0.0005 (2)
P2	0.0265 (3)	0.0220 (3)	0.0221 (3)	0.0024 (2)	0.0127 (2)	0.0011 (2)
P3	0.0285 (3)	0.0175 (3)	0.0251 (3)	0.0013 (2)	0.0163 (2)	0.0015 (2)
Cl1	0.0380 (3)	0.0280 (3)	0.0562 (4)	−0.0102 (2)	0.0208 (3)	−0.0094 (3)
Cl2	0.0503 (4)	0.0567 (4)	0.0311 (3)	0.0141 (3)	−0.0008 (3)	0.0012 (3)

Geometric parameters (Å, º) top

C1—O1	1.452 (3)	C10—C11	1.390 (3)
C1—C2	1.501 (3)	C10—H10	0.9500
C1—H1A	0.9900	C11—C12	1.379 (3)
C1—H1B	0.9900	C11—H11	0.9500
C2—O2	1.416 (3)	C12—C13	1.383 (3)
C2—H2A	0.9900	C12—H12	0.9500
C2—H2B	0.9900	C13—C14	1.378 (3)
C3—O2	1.416 (3)	C13—H13	0.9500
C3—C4	1.495 (3)	C14—H14	0.9500
C3—H3A	0.9900	C15—C16	1.393 (3)
C3—H3B	0.9900	C15—C20	1.400 (3)
C4—O3	1.416 (3)	C15—P3	1.797 (2)
C4—H4A	0.9900	C16—C17	1.382 (3)
C4—H4B	0.9900	C16—H16	0.9500
C5—O3	1.421 (3)	C17—C18	1.378 (3)
C5—C6	1.492 (3)	C17—H17	0.9500
C5—H5A	0.9900	C18—C19	1.387 (3)
C5—H5B	0.9900	C18—H18	0.9500
C6—O4	1.418 (3)	C19—C20	1.381 (3)
C6—H6A	0.9900	C19—H19	0.9500
C6—H6B	0.9900	C20—H20	0.9500
C7—O4	1.417 (3)	N1—P2	1.5703 (18)
C7—C8	1.493 (3)	N1—P1	1.5792 (17)
C7—H7A	0.9900	N2—P2	1.5653 (16)
C7—H7B	0.9900	N2—P3	1.6064 (16)
C8—O5	1.456 (3)	N3—P1	1.5694 (17)
C8—H8A	0.9900	N3—P3	1.6110 (17)
C8—H8B	0.9900	O1—P1	1.5633 (16)
C9—C10	1.395 (3)	O5—P2	1.5547 (15)
C9—C14	1.397 (3)	P1—Cl1	2.0196 (8)
C9—P3	1.799 (2)	P2—Cl2	2.0387 (11)

O1—C1—C2	106.71 (17)	C12—C11—H11	120.1
O1—C1—H1A	110.4	C10—C11—H11	120.1
C2—C1—H1A	110.4	C11—C12—C13	119.9 (2)
O1—C1—H1B	110.4	C11—C12—H12	120.0
C2—C1—H1B	110.4	C13—C12—H12	120.0
H1A—C1—H1B	108.6	C14—C13—C12	120.8 (2)
O2—C2—C1	108.36 (18)	C14—C13—H13	119.6
O2—C2—H2A	110.0	C12—C13—H13	119.6
C1—C2—H2A	110.0	C13—C14—C9	119.9 (2)
O2—C2—H2B	110.0	C13—C14—H14	120.1
C1—C2—H2B	110.0	C9—C14—H14	120.1
H2A—C2—H2B	108.4	C16—C15—C20	118.97 (19)
O2—C3—C4	107.83 (17)	C16—C15—P3	119.82 (15)
O2—C3—H3A	110.1	C20—C15—P3	121.16 (16)
C4—C3—H3A	110.1	C17—C16—C15	120.5 (2)
O2—C3—H3B	110.1	C17—C16—H16	119.8
C4—C3—H3B	110.1	C15—C16—H16	119.8
H3A—C3—H3B	108.5	C18—C17—C16	120.0 (2)
O3—C4—C3	108.78 (18)	C18—C17—H17	120.0
O3—C4—H4A	109.9	C16—C17—H17	120.0
C3—C4—H4A	109.9	C17—C18—C19	120.3 (2)
O3—C4—H4B	109.9	C17—C18—H18	119.8
C3—C4—H4B	109.9	C19—C18—H18	119.8
H4A—C4—H4B	108.3	C20—C19—C18	120.0 (2)
O3—C5—C6	110.09 (18)	C20—C19—H19	120.0
O3—C5—H5A	109.6	C18—C19—H19	120.0
C6—C5—H5A	109.6	C19—C20—C15	120.2 (2)
O3—C5—H5B	109.6	C19—C20—H20	119.9
C6—C5—H5B	109.6	C15—C20—H20	119.9
H5A—C5—H5B	108.2	P2—N1—P1	119.86 (10)
O4—C6—C5	109.46 (17)	P2—N2—P3	122.07 (11)
O4—C6—H6A	109.8	P1—N3—P3	122.09 (10)
C5—C6—H6A	109.8	C1—O1—P1	122.52 (13)
O4—C6—H6B	109.8	C2—O2—C3	113.29 (16)
C5—C6—H6B	109.8	C4—O3—C5	113.05 (16)
H6A—C6—H6B	108.2	C6—O4—C7	111.99 (16)
O4—C7—C8	108.20 (17)	C8—O5—P2	122.98 (13)
O4—C7—H7A	110.1	O1—P1—N3	113.53 (9)
C8—C7—H7A	110.1	O1—P1—N1	105.83 (9)
O4—C7—H7B	110.1	N3—P1—N1	119.44 (9)
C8—C7—H7B	110.1	O1—P1—Cl1	101.02 (7)
H7A—C7—H7B	108.4	N3—P1—Cl1	107.58 (7)
O5—C8—C7	108.07 (18)	N1—P1—Cl1	107.79 (8)
O5—C8—H8A	110.1	O5—P2—N2	112.20 (9)
C7—C8—H8A	110.1	O5—P2—N1	107.93 (9)
O5—C8—H8B	110.1	N2—P2—N1	119.85 (9)
C7—C8—H8B	110.1	O5—P2—Cl2	101.38 (7)
H8A—C8—H8B	108.4	N2—P2—Cl2	107.79 (7)
C10—C9—C14	119.1 (2)	N1—P2—Cl2	105.92 (7)
C10—C9—P3	123.73 (16)	N2—P3—N3	115.37 (9)
C14—C9—P3	117.18 (15)	N2—P3—C15	108.06 (9)
C11—C10—C9	120.4 (2)	N3—P3—C15	111.30 (9)
C11—C10—H10	119.8	N2—P3—C9	107.51 (9)
C9—C10—H10	119.8	N3—P3—C9	107.42 (9)
C12—C11—C10	119.9 (2)	C15—P3—C9	106.80 (9)

(4) top

Crystal data top

C₂₄H₃₀F₆N₃O₇P₃	F(000) = 1400
M_r = 679.42	D_x = 1.562 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 15.3839 (4) Å	Cell parameters from 10029 reflections
b = 8.0685 (2) Å	θ = 2.9–27.5°
c = 24.1935 (9) Å	µ = 0.29 mm⁻¹
β = 105.877 (1)°	T = 120 K
V = 2888.46 (15) Å³	Plate, colourless
Z = 4	0.18 × 0.10 × 0.03 mm

Data collection top

Nonius KappaCCD diffractometer	6488 independent reflections
Radiation source: Nonius FR591 rotating anode	3777 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −19→19
Absorption correction: multi-scan SORTAV (Blessing, 1997)	k = −10→8
T_min = 0.949, T_max = 0.991	l = −31→31
22797 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0463P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.006
6488 reflections	Δρ_max = 0.38 e Å⁻³
389 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (3)

Crystal data top

C₂₄H₃₀F₆N₃O₇P₃	V = 2888.46 (15) Å³
M_r = 679.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.3839 (4) Å	µ = 0.29 mm⁻¹
b = 8.0685 (2) Å	T = 120 K
c = 24.1935 (9) Å	0.18 × 0.10 × 0.03 mm
β = 105.877 (1)°

Data collection top

Nonius KappaCCD diffractometer	6488 independent reflections
Absorption correction: multi-scan SORTAV (Blessing, 1997)	3777 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.991	R_int = 0.083
22797 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 0.98	Δρ_max = 0.38 e Å⁻³
6488 reflections	Δρ_min = −0.38 e Å⁻³
389 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.30632 (19)	0.4338 (4)	0.06173 (11)	0.0266 (7)
H1A	0.2541	0.4680	0.0756	0.032*
H1B	0.3253	0.3214	0.0767	0.032*
C2	0.28124 (19)	0.4340 (4)	−0.00210 (12)	0.0269 (7)
C3	0.17222 (17)	0.9621 (4)	0.11787 (11)	0.0233 (6)
H3A	0.1375	1.0577	0.1262	0.028*
H3B	0.1631	0.8671	0.1416	0.028*
C4	0.14009 (19)	0.9187 (4)	0.05592 (12)	0.0269 (7)
C5	0.42024 (18)	0.4028 (4)	0.23410 (11)	0.0242 (6)
H5A	0.4098	0.2839	0.2401	0.029*
H5B	0.3717	0.4672	0.2439	0.029*
C6	0.51021 (19)	0.4538 (4)	0.27284 (11)	0.0259 (7)
H6A	0.5600	0.4020	0.2604	0.031*
H6B	0.5173	0.5758	0.2725	0.031*
C7	0.59025 (19)	0.4441 (4)	0.37193 (12)	0.0302 (7)
H7A	0.6436	0.4048	0.3603	0.036*
H7B	0.5901	0.3860	0.4080	0.036*
C8	0.60045 (18)	0.6261 (4)	0.38397 (12)	0.0271 (7)
H8A	0.6563	0.6474	0.4151	0.032*
H8B	0.6050	0.6860	0.3491	0.032*
C9	0.52831 (18)	0.8561 (4)	0.41135 (13)	0.0290 (7)
H9A	0.5325	0.9164	0.3765	0.035*
H9B	0.5827	0.8825	0.4430	0.035*
C10	0.44546 (18)	0.9086 (4)	0.42728 (12)	0.0283 (7)
H10A	0.4440	0.8518	0.4633	0.034*
H10B	0.4489	1.0293	0.4349	0.034*
C11	0.34972 (19)	0.9633 (4)	0.33199 (11)	0.0264 (7)
H11A	0.4027	1.0345	0.3334	0.032*
H11B	0.2957	1.0350	0.3260	0.032*
C12	0.3367 (2)	0.8411 (4)	0.28409 (11)	0.0278 (7)
H12A	0.3954	0.7913	0.2838	0.033*
H12B	0.2957	0.7512	0.2891	0.033*
C13	0.54897 (17)	0.9977 (3)	0.11897 (11)	0.0221 (6)
C14	0.60246 (19)	0.9212 (4)	0.08832 (12)	0.0291 (7)
H14	0.6233	0.8111	0.0976	0.035*
C15	0.6252 (2)	1.0045 (4)	0.04477 (13)	0.0369 (8)
H15	0.6619	0.9518	0.0241	0.044*
C16	0.5950 (2)	1.1645 (4)	0.03084 (13)	0.0353 (8)
H16	0.6100	1.2209	0.0002	0.042*
C17	0.54328 (19)	1.2420 (4)	0.06134 (13)	0.0323 (8)
H17	0.5231	1.3524	0.0520	0.039*
C18	0.52048 (18)	1.1603 (4)	0.10542 (12)	0.0267 (7)
H18	0.4853	1.2150	0.1266	0.032*
C19	0.60959 (17)	0.8989 (3)	0.23775 (11)	0.0199 (6)
C20	0.61259 (18)	1.0190 (3)	0.27932 (12)	0.0237 (6)
H20	0.5640	1.0952	0.2747	0.028*
C21	0.68568 (18)	1.0286 (4)	0.32734 (12)	0.0265 (7)
H21	0.6869	1.1105	0.3558	0.032*
C22	0.75699 (18)	0.9198 (4)	0.33423 (12)	0.0282 (7)
H22	0.8077	0.9280	0.3670	0.034*
C23	0.75470 (19)	0.7992 (4)	0.29360 (12)	0.0337 (8)
H23	0.8035	0.7233	0.2986	0.040*
C24	0.68116 (18)	0.7885 (4)	0.24537 (12)	0.0289 (7)
H24	0.6798	0.7051	0.2174	0.035*
N1	0.33017 (13)	0.7066 (3)	0.16249 (9)	0.0198 (5)
N2	0.43216 (14)	0.9822 (3)	0.18728 (9)	0.0209 (5)
N3	0.50191 (13)	0.6960 (3)	0.15597 (9)	0.0202 (5)
O1	0.37931 (11)	0.5486 (2)	0.08091 (7)	0.0220 (4)
O2	0.26641 (11)	1.0034 (2)	0.13145 (7)	0.0217 (4)
O3	0.41684 (12)	0.4304 (2)	0.17469 (7)	0.0217 (4)
O4	0.51064 (13)	0.3981 (2)	0.32838 (7)	0.0279 (5)
O5	0.52409 (12)	0.6830 (2)	0.40069 (8)	0.0272 (5)
O6	0.36358 (12)	0.8736 (2)	0.38419 (8)	0.0274 (5)
O7	0.29802 (12)	0.9283 (2)	0.23075 (7)	0.0227 (4)
F1	0.35004 (11)	0.3951 (2)	−0.02316 (7)	0.0376 (5)
F2	0.21548 (12)	0.3238 (2)	−0.02294 (7)	0.0463 (5)
F3	0.25101 (11)	0.5803 (2)	−0.02512 (7)	0.0338 (4)
F4	0.18624 (12)	0.7925 (2)	0.04156 (8)	0.0503 (5)
F5	0.14593 (12)	1.0434 (2)	0.02171 (7)	0.0453 (5)
F6	0.05335 (11)	0.8715 (2)	0.04226 (7)	0.0391 (5)
P1	0.40851 (4)	0.60711 (9)	0.14597 (3)	0.01907 (18)
P2	0.33745 (4)	0.89744 (9)	0.17773 (3)	0.01903 (18)
P3	0.51600 (4)	0.88728 (9)	0.17412 (3)	0.01985 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0275 (16)	0.0292 (19)	0.0224 (15)	−0.0102 (13)	0.0055 (12)	−0.0007 (13)
C2	0.0274 (17)	0.0273 (19)	0.0244 (16)	−0.0056 (13)	0.0042 (12)	−0.0062 (14)
C3	0.0178 (15)	0.0258 (17)	0.0242 (15)	0.0007 (12)	0.0024 (11)	0.0011 (13)
C4	0.0252 (17)	0.0261 (19)	0.0268 (16)	0.0028 (13)	0.0026 (12)	−0.0013 (14)
C5	0.0293 (16)	0.0214 (17)	0.0220 (15)	0.0009 (12)	0.0069 (12)	0.0025 (13)
C6	0.0327 (17)	0.0224 (17)	0.0217 (16)	0.0011 (12)	0.0060 (12)	0.0027 (13)
C7	0.0291 (17)	0.034 (2)	0.0227 (16)	0.0077 (13)	−0.0007 (12)	0.0011 (14)
C8	0.0218 (16)	0.035 (2)	0.0228 (15)	0.0050 (13)	0.0038 (12)	0.0013 (14)
C9	0.0273 (17)	0.0243 (19)	0.0324 (17)	−0.0019 (12)	0.0030 (13)	0.0009 (14)
C10	0.0301 (17)	0.0284 (19)	0.0216 (15)	0.0007 (13)	−0.0009 (12)	−0.0049 (13)
C11	0.0272 (16)	0.0287 (18)	0.0227 (16)	0.0072 (13)	0.0057 (12)	0.0013 (13)
C12	0.0363 (17)	0.0285 (18)	0.0172 (15)	0.0080 (13)	0.0047 (12)	0.0041 (13)
C13	0.0211 (15)	0.0197 (17)	0.0228 (15)	−0.0030 (12)	0.0015 (11)	−0.0028 (13)
C14	0.0369 (18)	0.0258 (19)	0.0293 (17)	−0.0008 (13)	0.0172 (13)	−0.0024 (14)
C15	0.0431 (19)	0.039 (2)	0.0346 (19)	−0.0091 (16)	0.0205 (15)	−0.0083 (16)
C16	0.0375 (18)	0.040 (2)	0.0249 (17)	−0.0162 (15)	0.0028 (13)	0.0027 (15)
C17	0.0318 (17)	0.0271 (19)	0.0330 (18)	−0.0033 (13)	0.0002 (14)	0.0059 (15)
C18	0.0222 (15)	0.0278 (19)	0.0272 (16)	0.0005 (12)	0.0018 (12)	0.0016 (14)
C19	0.0184 (14)	0.0211 (17)	0.0200 (14)	−0.0001 (12)	0.0052 (11)	0.0024 (13)
C20	0.0249 (16)	0.0188 (17)	0.0265 (16)	0.0004 (12)	0.0057 (12)	0.0018 (13)
C21	0.0311 (17)	0.0244 (18)	0.0232 (16)	−0.0054 (13)	0.0060 (12)	−0.0042 (13)
C22	0.0226 (16)	0.034 (2)	0.0245 (16)	−0.0037 (13)	−0.0001 (12)	0.0024 (14)
C23	0.0241 (16)	0.042 (2)	0.0324 (18)	0.0106 (14)	0.0034 (13)	0.0006 (16)
C24	0.0280 (16)	0.0311 (19)	0.0264 (16)	0.0044 (13)	0.0058 (12)	−0.0045 (14)
N1	0.0189 (12)	0.0187 (14)	0.0223 (12)	−0.0008 (9)	0.0066 (9)	−0.0003 (10)
N2	0.0212 (12)	0.0146 (13)	0.0271 (13)	0.0000 (9)	0.0068 (10)	−0.0033 (10)
N3	0.0183 (12)	0.0164 (13)	0.0248 (12)	0.0010 (9)	0.0041 (9)	−0.0031 (10)
O1	0.0263 (11)	0.0209 (11)	0.0184 (10)	−0.0057 (8)	0.0054 (8)	−0.0037 (8)
O2	0.0175 (10)	0.0227 (12)	0.0227 (10)	−0.0001 (8)	0.0018 (7)	0.0025 (8)
O3	0.0312 (11)	0.0159 (11)	0.0181 (10)	0.0009 (8)	0.0067 (8)	−0.0003 (8)
O4	0.0355 (12)	0.0285 (13)	0.0172 (10)	0.0023 (9)	0.0028 (8)	0.0045 (9)
O5	0.0242 (11)	0.0248 (13)	0.0334 (12)	−0.0005 (8)	0.0093 (8)	−0.0019 (9)
O6	0.0250 (11)	0.0361 (13)	0.0192 (10)	0.0004 (9)	0.0031 (8)	0.0011 (9)
O7	0.0256 (10)	0.0230 (12)	0.0198 (10)	0.0050 (8)	0.0067 (8)	0.0016 (8)
F1	0.0409 (11)	0.0447 (12)	0.0277 (10)	0.0095 (8)	0.0102 (8)	−0.0097 (8)
F2	0.0553 (12)	0.0455 (13)	0.0307 (10)	−0.0281 (9)	−0.0007 (8)	−0.0076 (9)
F3	0.0355 (10)	0.0327 (11)	0.0290 (9)	0.0060 (8)	0.0017 (7)	0.0034 (8)
F4	0.0462 (12)	0.0542 (14)	0.0426 (11)	0.0211 (10)	−0.0012 (9)	−0.0229 (10)
F5	0.0498 (12)	0.0541 (14)	0.0262 (10)	−0.0051 (9)	0.0008 (8)	0.0107 (9)
F6	0.0292 (10)	0.0410 (12)	0.0382 (10)	−0.0032 (8)	−0.0060 (7)	−0.0069 (9)
P1	0.0211 (4)	0.0172 (4)	0.0181 (4)	0.0004 (3)	0.0040 (3)	−0.0006 (3)
P2	0.0185 (4)	0.0194 (4)	0.0183 (4)	0.0018 (3)	0.0033 (3)	−0.0004 (3)
P3	0.0175 (4)	0.0200 (4)	0.0211 (4)	0.0007 (3)	0.0037 (3)	−0.0026 (3)

Geometric parameters (Å, º) top

C1—O1	1.431 (3)	C11—H11B	0.9900
C1—C2	1.486 (4)	C12—O7	1.447 (3)
C1—H1A	0.9900	C12—H12A	0.9900
C1—H1B	0.9900	C12—H12B	0.9900
C2—F1	1.332 (3)	C13—C14	1.393 (4)
C2—F3	1.333 (3)	C13—C18	1.394 (4)
C2—F2	1.338 (3)	C13—P3	1.789 (3)
C3—O2	1.434 (3)	C14—C15	1.373 (4)
C3—C4	1.486 (4)	C14—H14	0.9500
C3—H3A	0.9900	C15—C16	1.382 (5)
C3—H3B	0.9900	C15—H15	0.9500
C4—F5	1.322 (3)	C16—C17	1.375 (4)
C4—F6	1.339 (3)	C16—H16	0.9500
C4—F4	1.340 (3)	C17—C18	1.378 (4)
C5—O3	1.441 (3)	C17—H17	0.9500
C5—C6	1.501 (4)	C18—H18	0.9500
C5—H5A	0.9900	C19—C24	1.389 (4)
C5—H5B	0.9900	C19—C20	1.389 (4)
C6—O4	1.415 (3)	C19—P3	1.800 (3)
C6—H6A	0.9900	C20—C21	1.380 (4)
C6—H6B	0.9900	C20—H20	0.9500
C7—O4	1.429 (3)	C21—C22	1.379 (4)
C7—C8	1.497 (4)	C21—H21	0.9500
C7—H7A	0.9900	C22—C23	1.377 (4)
C7—H7B	0.9900	C22—H22	0.9500
C8—O5	1.419 (3)	C23—C24	1.388 (4)
C8—H8A	0.9900	C23—H23	0.9500
C8—H8B	0.9900	C24—H24	0.9500
C9—O5	1.418 (3)	N1—P2	1.581 (2)
C9—C10	1.491 (4)	N1—P1	1.587 (2)
C9—H9A	0.9900	N2—P2	1.569 (2)
C9—H9B	0.9900	N2—P3	1.605 (2)
C10—O6	1.426 (3)	N3—P1	1.565 (2)
C10—H10A	0.9900	N3—P3	1.603 (2)
C10—H10B	0.9900	O1—P1	1.5861 (18)
C11—O6	1.420 (3)	O2—P2	1.5840 (18)
C11—C12	1.493 (4)	O3—P1	1.5763 (19)
C11—H11A	0.9900	O7—P2	1.5814 (18)

O1—C1—C2	107.1 (2)	C11—C12—H12A	110.1
O1—C1—H1A	110.3	O7—C12—H12B	110.1
C2—C1—H1A	110.3	C11—C12—H12B	110.1
O1—C1—H1B	110.3	H12A—C12—H12B	108.5
C2—C1—H1B	110.3	C14—C13—C18	119.0 (3)
H1A—C1—H1B	108.6	C14—C13—P3	120.4 (2)
F1—C2—F3	105.8 (2)	C18—C13—P3	120.6 (2)
F1—C2—F2	107.3 (2)	C15—C14—C13	120.2 (3)
F3—C2—F2	106.8 (2)	C15—C14—H14	119.9
F1—C2—C1	113.0 (2)	C13—C14—H14	119.9
F3—C2—C1	113.4 (2)	C14—C15—C16	120.3 (3)
F2—C2—C1	110.2 (2)	C14—C15—H15	119.9
O2—C3—C4	108.8 (2)	C16—C15—H15	119.9
O2—C3—H3A	109.9	C17—C16—C15	119.9 (3)
C4—C3—H3A	109.9	C17—C16—H16	120.0
O2—C3—H3B	109.9	C15—C16—H16	120.0
C4—C3—H3B	109.9	C16—C17—C18	120.4 (3)
H3A—C3—H3B	108.3	C16—C17—H17	119.8
F5—C4—F6	107.2 (2)	C18—C17—H17	119.8
F5—C4—F4	106.5 (2)	C17—C18—C13	120.1 (3)
F6—C4—F4	106.4 (2)	C17—C18—H18	119.9
F5—C4—C3	113.0 (2)	C13—C18—H18	119.9
F6—C4—C3	110.5 (2)	C24—C19—C20	118.9 (2)
F4—C4—C3	112.8 (2)	C24—C19—P3	120.0 (2)
O3—C5—C6	110.9 (2)	C20—C19—P3	121.1 (2)
O3—C5—H5A	109.5	C21—C20—C19	120.4 (3)
C6—C5—H5A	109.5	C21—C20—H20	119.8
O3—C5—H5B	109.5	C19—C20—H20	119.8
C6—C5—H5B	109.5	C22—C21—C20	120.3 (3)
H5A—C5—H5B	108.1	C22—C21—H21	119.9
O4—C6—C5	105.6 (2)	C20—C21—H21	119.9
O4—C6—H6A	110.6	C23—C22—C21	120.0 (3)
C5—C6—H6A	110.6	C23—C22—H22	120.0
O4—C6—H6B	110.6	C21—C22—H22	120.0
C5—C6—H6B	110.6	C22—C23—C24	120.0 (3)
H6A—C6—H6B	108.7	C22—C23—H23	120.0
O4—C7—C8	114.9 (2)	C24—C23—H23	120.0
O4—C7—H7A	108.5	C23—C24—C19	120.4 (3)
C8—C7—H7A	108.5	C23—C24—H24	119.8
O4—C7—H7B	108.5	C19—C24—H24	119.8
C8—C7—H7B	108.5	P2—N1—P1	122.76 (13)
H7A—C7—H7B	107.5	P2—N2—P3	121.81 (14)
O5—C8—C7	108.8 (2)	P1—N3—P3	122.24 (13)
O5—C8—H8A	109.9	C1—O1—P1	119.89 (16)
C7—C8—H8A	109.9	C3—O2—P2	119.68 (17)
O5—C8—H8B	109.9	C5—O3—P1	123.76 (17)
C7—C8—H8B	109.9	C6—O4—C7	113.4 (2)
H8A—C8—H8B	108.3	C9—O5—C8	111.7 (2)
O5—C9—C10	109.1 (2)	C11—O6—C10	115.9 (2)
O5—C9—H9A	109.9	C12—O7—P2	119.43 (17)
C10—C9—H9A	109.9	N3—P1—O3	112.73 (11)
O5—C9—H9B	109.9	N3—P1—O1	106.78 (11)
C10—C9—H9B	109.9	O3—P1—O1	97.76 (10)
H9A—C9—H9B	108.3	N3—P1—N1	117.24 (12)
O6—C10—C9	113.7 (2)	O3—P1—N1	108.79 (11)
O6—C10—H10A	108.8	O1—P1—N1	111.83 (11)
C9—C10—H10A	108.8	N2—P2—N1	117.58 (12)
O6—C10—H10B	108.8	N2—P2—O7	111.04 (11)
C9—C10—H10B	108.8	N1—P2—O7	108.91 (11)
H10A—C10—H10B	107.7	N2—P2—O2	107.59 (11)
O6—C11—C12	108.0 (2)	N1—P2—O2	111.70 (11)
O6—C11—H11A	110.1	O7—P2—O2	98.33 (10)
C12—C11—H11A	110.1	N3—P3—N2	117.27 (11)
O6—C11—H11B	110.1	N3—P3—C13	108.64 (12)
C12—C11—H11B	110.1	N2—P3—C13	108.51 (13)
H11A—C11—H11B	108.4	N3—P3—C19	107.51 (12)
O7—C12—C11	107.8 (2)	N2—P3—C19	107.68 (12)
O7—C12—H12A	110.1	C13—P3—C19	106.76 (12)

O1—C1—C2—F1	57.5 (3)	C5—O3—P1—N3	84.1 (2)
O1—C1—C2—F3	−62.8 (3)	C5—O3—P1—O1	−164.04 (18)
O1—C1—C2—F2	177.5 (2)	C5—O3—P1—N1	−47.8 (2)
O2—C3—C4—F5	−62.9 (3)	C1—O1—P1—N3	167.0 (2)
O2—C3—C4—F6	177.0 (2)	C1—O1—P1—O3	50.4 (2)
O2—C3—C4—F4	58.0 (3)	C1—O1—P1—N1	−63.5 (2)
O3—C5—C6—O4	−171.3 (2)	P2—N1—P1—N3	10.9 (2)
O4—C7—C8—O5	58.3 (3)	P2—N1—P1—O3	140.30 (14)
O5—C9—C10—O6	−58.9 (3)	P2—N1—P1—O1	−112.85 (15)
O6—C11—C12—O7	164.2 (2)	P3—N2—P2—N1	8.0 (2)
C18—C13—C14—C15	−1.1 (4)	P3—N2—P2—O7	134.31 (15)
P3—C13—C14—C15	177.9 (2)	P3—N2—P2—O2	−119.14 (16)
C13—C14—C15—C16	−0.2 (4)	P1—N1—P2—N2	−11.0 (2)
C14—C15—C16—C17	1.2 (4)	P1—N1—P2—O7	−138.35 (14)
C15—C16—C17—C18	−0.7 (4)	P1—N1—P2—O2	114.12 (15)
C16—C17—C18—C13	−0.7 (4)	C12—O7—P2—N2	−73.2 (2)
C14—C13—C18—C17	1.6 (4)	C12—O7—P2—N1	57.8 (2)
P3—C13—C18—C17	−177.4 (2)	C12—O7—P2—O2	174.21 (19)
C24—C19—C20—C21	0.1 (4)	C3—O2—P2—N2	−174.73 (18)
P3—C19—C20—C21	−178.7 (2)	C3—O2—P2—N1	54.8 (2)
C19—C20—C21—C22	0.7 (4)	C3—O2—P2—O7	−59.45 (19)
C20—C21—C22—C23	−1.1 (4)	P1—N3—P3—N2	5.3 (2)
C21—C22—C23—C24	0.8 (4)	P1—N3—P3—C13	−118.16 (16)
C22—C23—C24—C19	0.0 (4)	P1—N3—P3—C19	126.65 (16)
C20—C19—C24—C23	−0.5 (4)	P2—N2—P3—N3	−5.2 (2)
P3—C19—C24—C23	178.3 (2)	P2—N2—P3—C13	118.26 (16)
C2—C1—O1—P1	166.95 (18)	P2—N2—P3—C19	−126.53 (16)
C4—C3—O2—P2	−119.2 (2)	C14—C13—P3—N3	−33.9 (3)
C6—C5—O3—P1	−73.5 (3)	C18—C13—P3—N3	145.1 (2)
C5—C6—O4—C7	−176.9 (2)	C14—C13—P3—N2	−162.4 (2)
C8—C7—O4—C6	67.3 (3)	C18—C13—P3—N2	16.6 (2)
C10—C9—O5—C8	178.6 (2)	C14—C13—P3—C19	81.8 (2)
C7—C8—O5—C9	−178.5 (2)	C18—C13—P3—C19	−99.2 (2)
C12—C11—O6—C10	123.1 (2)	C24—C19—P3—N3	33.5 (3)
C9—C10—O6—C11	−66.5 (3)	C20—C19—P3—N3	−147.7 (2)
C11—C12—O7—P2	134.7 (2)	C24—C19—P3—N2	160.7 (2)
P3—N3—P1—O3	−135.42 (14)	C20—C19—P3—N2	−20.5 (3)
P3—N3—P1—O1	118.37 (15)	C24—C19—P3—C13	−82.9 (2)
P3—N3—P1—N1	−7.9 (2)	C20—C19—P3—C13	95.8 (2)

(5) top

Crystal data top

C₃₂H₃₆N₃O₇P₃	Z = 2
M_r = 667.55	F(000) = 700
Triclinic, P1	D_x = 1.385 Mg m⁻³
a = 10.166 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.105 (2) Å	Cell parameters from 13461 reflections
c = 13.313 (3) Å	θ = 2.9–27.5°
α = 88.86 (3)°	µ = 0.24 mm⁻¹
β = 86.54 (3)°	T = 150 K
γ = 78.14 (3)°	Block, colourless
V = 1600.4 (6) Å³	0.20 × 0.15 × 0.10 mm

Data collection top

Bruker-Nonius KappaCCD diffractometer	12306 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	8750 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ϕ & ω scans	h = −13→11
Absorption correction: multi-scan SORTAV (Blessing, 1997)	k = −15→13
T_min = 0.954, T_max = 0.977	l = −17→16
24220 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.054	w = 1/[σ²(F_o²) + (0.0651P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.132	(Δ/σ)_max = 0.002
S = 0.94	Δρ_max = 0.81 e Å⁻³
12306 reflections	Δρ_min = −0.40 e Å⁻³
824 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
22 restraints	Extinction coefficient: 0.0054 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.03 (7)

Crystal data top

C₃₂H₃₆N₃O₇P₃	γ = 78.14 (3)°
M_r = 667.55	V = 1600.4 (6) Å³
Triclinic, P1	Z = 2
a = 10.166 (2) Å	Mo Kα radiation
b = 12.105 (2) Å	µ = 0.24 mm⁻¹
c = 13.313 (3) Å	T = 150 K
α = 88.86 (3)°	0.20 × 0.15 × 0.10 mm
β = 86.54 (3)°

Data collection top

Bruker-Nonius KappaCCD diffractometer	12306 independent reflections
Absorption correction: multi-scan SORTAV (Blessing, 1997)	8750 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.977	R_int = 0.061
24220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.132	Δρ_max = 0.81 e Å⁻³
S = 0.94	Δρ_min = −0.40 e Å⁻³
12306 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
824 parameters	Absolute structure parameter: 0.03 (7)
22 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6413 (4)	0.3165 (4)	0.7512 (3)	0.0331 (10)
C2	0.7215 (5)	0.3322 (4)	0.8277 (3)	0.0451 (12)
H2	0.7506	0.4015	0.8326	0.054*
C3	0.7592 (5)	0.2472 (6)	0.8971 (4)	0.0608 (16)
H3	0.8151	0.2575	0.9493	0.073*
C4	0.7162 (6)	0.1488 (6)	0.8906 (4)	0.0634 (17)
H4	0.7429	0.0901	0.9382	0.076*
C5	0.6339 (6)	0.1332 (5)	0.8155 (4)	0.0563 (14)
H5	0.6035	0.0643	0.8118	0.068*
C6	0.5956 (5)	0.2186 (4)	0.7453 (3)	0.0419 (11)
H6	0.5383	0.2089	0.6938	0.050*
C7	0.4772 (4)	0.1248 (3)	0.4866 (3)	0.0287 (9)
C8	0.3498 (4)	0.1431 (4)	0.5301 (3)	0.0407 (11)
H8	0.2823	0.2033	0.5076	0.049*
C9	0.3204 (5)	0.0721 (5)	0.6078 (4)	0.0545 (14)
H9	0.2309	0.0821	0.6366	0.065*
C10	0.4186 (5)	−0.0122 (4)	0.6437 (4)	0.0483 (13)
H10	0.3984	−0.0589	0.6982	0.058*
C11	0.5449 (5)	−0.0277 (4)	0.5998 (4)	0.0452 (12)
H11	0.6128	−0.0861	0.6245	0.054*
C12	0.5784 (4)	0.0388 (4)	0.5200 (3)	0.0369 (11)
H12	0.6670	0.0262	0.4894	0.044*
C13	0.7370 (5)	0.5866 (4)	0.6018 (3)	0.0389 (11)
H13A	0.8254	0.5373	0.6132	0.047*
H13B	0.6919	0.6109	0.6680	0.047*
C14	0.7560 (5)	0.6874 (4)	0.5402 (4)	0.0462 (12)
H14A	0.6678	0.7301	0.5196	0.055*
H14B	0.7974	0.7378	0.5803	0.055*
C15	0.8038 (6)	0.7150 (4)	0.3664 (4)	0.0607 (16)
H15A	0.8084	0.7946	0.3779	0.073*
H15B	0.7100	0.7125	0.3523	0.073*
C16	0.8930 (7)	0.6717 (5)	0.2809 (4)	0.0639 (16)
H16A	0.8767	0.7250	0.2235	0.077*
H16B	0.9877	0.6644	0.2983	0.077*
C17	0.9586 (5)	0.5201 (4)	0.1709 (3)	0.0418 (12)
H17A	1.0528	0.5196	0.1862	0.050*
H17B	0.9373	0.5677	0.1103	0.050*
C18	0.9424 (4)	0.4047 (4)	0.1522 (3)	0.0401 (11)
H18A	1.0162	0.3678	0.1046	0.048*
H18B	0.9502	0.3614	0.2162	0.048*
C19	0.7362 (5)	0.3359 (4)	0.1681 (3)	0.0378 (11)
H19A	0.7957	0.2682	0.1954	0.045*
H19B	0.6742	0.3101	0.1234	0.045*
C20	0.6557 (4)	0.4026 (4)	0.2535 (3)	0.0342 (10)
H20A	0.7169	0.4217	0.3025	0.041*
H20B	0.6016	0.4737	0.2276	0.041*
C21	1.0072 (4)	0.2632 (3)	0.4118 (3)	0.0265 (9)
C22	1.0357 (4)	0.3692 (4)	0.4182 (3)	0.0328 (10)
H22	0.9797	0.4242	0.4603	0.039*
C23	1.1454 (5)	0.3964 (4)	0.3636 (3)	0.0399 (11)
H23	1.1645	0.4695	0.3693	0.048*
C24	1.2276 (4)	0.3175 (4)	0.3008 (4)	0.0429 (12)
H24	1.3030	0.3360	0.2637	0.052*
C25	1.1980 (5)	0.2116 (4)	0.2930 (4)	0.0395 (11)
C26	1.0892 (4)	0.1839 (4)	0.3477 (3)	0.0351 (10)
H26	1.0699	0.1109	0.3418	0.042*
C27	0.9209 (4)	0.0982 (3)	0.5444 (3)	0.0282 (9)
C28	0.9400 (4)	0.0970 (4)	0.6463 (3)	0.0361 (11)
C29	0.9899 (5)	−0.0047 (4)	0.6948 (4)	0.0459 (13)
H29	1.0030	−0.0053	0.7649	0.055*
C30	1.0201 (4)	−0.1037 (4)	0.6426 (4)	0.0500 (14)
H30	1.0559	−0.1722	0.6763	0.060*
C31	0.9988 (5)	−0.1050 (4)	0.5408 (4)	0.0454 (12)
H31	1.0184	−0.1740	0.5050	0.055*
C32	0.9480 (4)	−0.0034 (4)	0.4915 (4)	0.0395 (11)
H32	0.9320	−0.0034	0.4220	0.047*
C33	0.0458 (4)	0.9098 (3)	0.9875 (3)	0.0291 (10)
C34	0.0976 (5)	0.9953 (4)	1.0268 (4)	0.0443 (12)
H34	0.1770	1.0155	0.9976	0.053*
C35	0.0282 (6)	1.0515 (4)	1.1119 (4)	0.0506 (13)
C36	−0.0859 (6)	1.0204 (4)	1.1542 (4)	0.0458 (12)
H36	−0.1319	1.0589	1.2117	0.055*
C37	−0.1327 (5)	0.9345 (4)	1.1137 (4)	0.0479 (13)
H37	−0.2110	0.9130	1.1435	0.057*
C38	−0.0665 (5)	0.8777 (4)	1.0285 (4)	0.0415 (12)
H38	−0.0993	0.8180	1.0000	0.050*
C39	0.2650 (4)	0.7026 (4)	1.2527 (3)	0.0302 (10)
C40	0.2273 (5)	0.8133 (4)	1.2833 (4)	0.0407 (11)
H40	0.1687	0.8674	1.2453	0.049*
C41	0.2776 (5)	0.8433 (5)	1.3715 (4)	0.0505 (13)
H41	0.2526	0.9190	1.3945	0.061*
C42	0.3632 (5)	0.7643 (5)	1.4257 (4)	0.0541 (14)
H42	0.3982	0.7851	1.4855	0.065*
C43	0.3970 (5)	0.6557 (5)	1.3923 (4)	0.0502 (13)
H43	0.4564	0.6012	1.4293	0.060*
C44	0.3479 (4)	0.6240 (4)	1.3078 (4)	0.0382 (11)
C45	0.3484 (4)	0.6531 (4)	0.7381 (3)	0.0354 (10)
H45A	0.3940	0.5990	0.7880	0.042*
H45B	0.4138	0.6965	0.7083	0.042*
C46	0.2970 (5)	0.5914 (4)	0.6580 (3)	0.0379 (11)
H46A	0.2412	0.6456	0.6132	0.045*
H46B	0.3732	0.5467	0.6169	0.045*
C47	0.1847 (8)	0.4425 (6)	0.6381 (5)	0.0812 (11)
H47A	0.2663	0.4009	0.6007	0.097*
H47B	0.1226	0.4834	0.5890	0.097*
C48	0.1178 (7)	0.3620 (5)	0.6990 (4)	0.0670 (17)
H48A	0.0446	0.4038	0.7444	0.080*
H48B	0.0790	0.3143	0.6542	0.080*
C49	0.1786 (7)	0.2199 (5)	0.8270 (4)	0.0812 (11)
H49A	0.0972	0.1961	0.8054	0.097*
H49B	0.2507	0.1517	0.8327	0.097*
C50	0.1476 (7)	0.2783 (6)	0.9297 (4)	0.0812 (11)
H50A	0.0805	0.3489	0.9196	0.097*
H50B	0.1026	0.2291	0.9742	0.097*
C51	0.3242 (5)	0.3829 (4)	0.9362 (4)	0.0468 (12)
H51A	0.2619	0.4480	0.9076	0.056*
H51B	0.3850	0.3447	0.8808	0.056*
C52	0.4052 (5)	0.4229 (4)	1.0141 (4)	0.0461 (12)
H52A	0.4550	0.3566	1.0503	0.055*
H52B	0.4720	0.4619	0.9798	0.055*
C53	0.6390 (4)	0.7226 (3)	0.9300 (3)	0.0275 (9)
C54	0.7292 (4)	0.6270 (4)	0.9567 (3)	0.0357 (10)
H54	0.7044	0.5801	1.0096	0.043*
C55	0.8546 (4)	0.5984 (4)	0.9082 (3)	0.0386 (11)
H55	0.9153	0.5317	0.9273	0.046*
C56	0.8927 (5)	0.6657 (4)	0.8319 (4)	0.0409 (12)
C57	0.8018 (5)	0.7609 (4)	0.8038 (3)	0.0417 (12)
H57	0.8267	0.8073	0.7506	0.050*
C58	0.6765 (4)	0.7895 (4)	0.8515 (3)	0.0338 (10)
H58	0.6151	0.8551	0.8311	0.041*
C59	0.4922 (4)	0.8812 (4)	1.0727 (3)	0.0284 (9)
C60	0.4746 (5)	0.9894 (4)	1.0319 (4)	0.0382 (11)
C61	0.4885 (5)	1.0797 (4)	1.0905 (4)	0.0460 (12)
H61	0.4764	1.1536	1.0623	0.055*
C62	0.5198 (5)	1.0618 (4)	1.1886 (4)	0.0448 (12)
H62	0.5314	1.1231	1.2282	0.054*
C63	0.5347 (5)	0.9544 (4)	1.2310 (4)	0.0441 (12)
H63	0.5535	0.9430	1.2999	0.053*
C64	0.5223 (4)	0.8640 (4)	1.1729 (3)	0.0355 (10)
H64	0.5343	0.7903	1.2014	0.043*
N1	0.5592 (3)	0.3621 (3)	0.4977 (3)	0.0306 (8)
N2	0.7557 (3)	0.2107 (3)	0.4021 (2)	0.0267 (8)
N3	0.8121 (3)	0.3259 (3)	0.5637 (2)	0.0269 (8)
N4	0.2159 (3)	0.6647 (3)	0.9743 (3)	0.0333 (8)
N5	0.4455 (3)	0.6635 (3)	1.0654 (2)	0.0281 (8)
N6	0.3679 (3)	0.8139 (3)	0.9135 (3)	0.0308 (8)
O1	0.6040 (3)	0.4035 (2)	0.6831 (2)	0.0337 (7)
O2	0.5028 (3)	0.1934 (2)	0.4043 (2)	0.0308 (7)
O3	0.6561 (3)	0.5265 (2)	0.5483 (2)	0.0336 (7)
O4	0.8407 (3)	0.6500 (3)	0.4540 (2)	0.0461 (8)
O5	0.8707 (3)	0.5642 (3)	0.2530 (2)	0.0455 (8)
O6	0.8151 (3)	0.4011 (3)	0.1116 (2)	0.0367 (7)
O7	0.5671 (3)	0.3340 (2)	0.3024 (2)	0.0327 (7)
O8	0.1070 (3)	0.8590 (3)	0.8981 (2)	0.0365 (7)
O9	0.2117 (3)	0.6751 (3)	1.1640 (2)	0.0442 (8)
O10	0.2334 (3)	0.7287 (3)	0.7860 (2)	0.0389 (8)
O11	0.2198 (3)	0.5201 (3)	0.7055 (2)	0.0454 (8)
O12	0.2194 (5)	0.2939 (4)	0.7559 (3)	0.0854 (14)
O13	0.2498 (3)	0.3065 (3)	0.9829 (2)	0.0481 (9)
O14	0.3225 (3)	0.4986 (2)	1.0860 (2)	0.0382 (7)
P1	0.66234 (11)	0.39684 (9)	0.56834 (8)	0.0281 (2)
P2	0.60464 (10)	0.27688 (9)	0.40729 (8)	0.0269 (2)
P3	0.86202 (10)	0.22965 (9)	0.48078 (8)	0.0251 (2)
P4	0.24002 (11)	0.76270 (10)	0.89930 (8)	0.0303 (3)
P5	0.30434 (11)	0.62864 (10)	1.06672 (8)	0.0303 (3)
P6	0.47563 (11)	0.76544 (9)	0.99517 (8)	0.0266 (2)
H25	1.256 (4)	0.158 (3)	0.251 (3)	0.021 (10)*
H28	0.927 (3)	0.169 (3)	0.690 (2)	0.001 (8)*
H35	0.068 (5)	1.123 (4)	1.148 (3)	0.048 (13)*
H44	0.371 (5)	0.546 (4)	1.286 (3)	0.041 (13)*
H56	0.979 (5)	0.648 (4)	0.795 (3)	0.038 (12)*
H60	0.441 (4)	1.001 (3)	0.964 (3)	0.025 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.034 (2)	0.037 (3)	0.025 (2)	−0.003 (2)	0.0033 (18)	−0.0053 (19)
C2	0.036 (3)	0.063 (3)	0.037 (3)	−0.014 (2)	0.003 (2)	−0.014 (2)
C3	0.042 (3)	0.108 (5)	0.033 (3)	−0.017 (3)	−0.004 (2)	0.000 (3)
C4	0.059 (4)	0.078 (4)	0.041 (3)	0.008 (3)	0.010 (3)	0.018 (3)
C5	0.078 (4)	0.046 (3)	0.043 (3)	−0.012 (3)	0.006 (3)	0.009 (2)
C6	0.046 (3)	0.048 (3)	0.034 (3)	−0.015 (2)	−0.001 (2)	−0.006 (2)
C7	0.033 (2)	0.031 (2)	0.026 (2)	−0.0150 (19)	−0.0025 (18)	−0.0034 (18)
C8	0.025 (2)	0.049 (3)	0.048 (3)	−0.010 (2)	−0.002 (2)	0.008 (2)
C9	0.034 (3)	0.073 (4)	0.057 (3)	−0.016 (3)	0.010 (2)	0.012 (3)
C10	0.051 (3)	0.046 (3)	0.049 (3)	−0.013 (3)	0.002 (3)	0.009 (2)
C11	0.057 (3)	0.029 (3)	0.048 (3)	−0.004 (2)	−0.004 (3)	0.003 (2)
C12	0.031 (2)	0.033 (2)	0.045 (3)	−0.0025 (19)	0.001 (2)	−0.006 (2)
C13	0.045 (3)	0.036 (3)	0.038 (3)	−0.014 (2)	0.000 (2)	−0.004 (2)
C14	0.054 (3)	0.032 (3)	0.053 (3)	−0.010 (2)	0.009 (3)	−0.013 (2)
C15	0.085 (4)	0.030 (3)	0.066 (4)	−0.011 (3)	−0.003 (3)	0.004 (3)
C16	0.101 (5)	0.044 (3)	0.049 (3)	−0.022 (3)	−0.003 (3)	0.008 (3)
C17	0.039 (3)	0.055 (3)	0.034 (3)	−0.017 (2)	−0.005 (2)	0.011 (2)
C18	0.027 (2)	0.058 (3)	0.033 (3)	−0.006 (2)	0.0038 (19)	0.003 (2)
C19	0.036 (3)	0.041 (3)	0.038 (3)	−0.011 (2)	−0.002 (2)	0.002 (2)
C20	0.027 (2)	0.035 (3)	0.039 (3)	−0.0058 (19)	0.0041 (19)	0.006 (2)
C21	0.0155 (19)	0.035 (2)	0.029 (2)	−0.0065 (17)	−0.0024 (16)	0.0057 (18)
C22	0.035 (2)	0.032 (3)	0.032 (2)	−0.0094 (19)	0.0017 (19)	−0.0021 (19)
C23	0.039 (3)	0.049 (3)	0.038 (3)	−0.024 (2)	−0.001 (2)	0.007 (2)
C24	0.023 (2)	0.065 (3)	0.042 (3)	−0.013 (2)	−0.004 (2)	0.012 (2)
C25	0.027 (2)	0.043 (3)	0.045 (3)	−0.003 (2)	0.007 (2)	−0.003 (2)
C26	0.029 (2)	0.042 (3)	0.032 (2)	−0.003 (2)	−0.0002 (19)	0.003 (2)
C27	0.0147 (19)	0.031 (2)	0.038 (2)	−0.0032 (17)	0.0011 (17)	0.0060 (19)
C28	0.026 (2)	0.048 (3)	0.036 (3)	−0.010 (2)	−0.0015 (19)	0.003 (2)
C29	0.032 (2)	0.054 (3)	0.048 (3)	−0.004 (2)	−0.005 (2)	0.025 (3)
C30	0.025 (2)	0.046 (3)	0.074 (4)	0.000 (2)	0.005 (2)	0.031 (3)
C31	0.039 (3)	0.033 (3)	0.061 (3)	−0.005 (2)	0.012 (2)	0.011 (2)
C32	0.033 (2)	0.037 (3)	0.047 (3)	−0.006 (2)	0.003 (2)	0.007 (2)
C33	0.023 (2)	0.035 (2)	0.025 (2)	0.0032 (18)	−0.0017 (17)	−0.0003 (18)
C34	0.045 (3)	0.038 (3)	0.049 (3)	−0.010 (2)	0.004 (2)	−0.010 (2)
C35	0.067 (4)	0.038 (3)	0.045 (3)	−0.006 (3)	0.000 (3)	−0.007 (2)
C36	0.057 (3)	0.039 (3)	0.032 (3)	0.010 (2)	0.006 (2)	−0.002 (2)
C37	0.042 (3)	0.046 (3)	0.050 (3)	−0.002 (2)	0.010 (2)	0.005 (3)
C38	0.032 (3)	0.040 (3)	0.052 (3)	−0.003 (2)	−0.007 (2)	−0.006 (2)
C39	0.019 (2)	0.046 (3)	0.026 (2)	−0.0094 (19)	0.0063 (17)	−0.0040 (19)
C40	0.029 (2)	0.041 (3)	0.048 (3)	−0.002 (2)	0.006 (2)	0.008 (2)
C41	0.048 (3)	0.050 (3)	0.054 (3)	−0.014 (3)	0.014 (3)	−0.021 (3)
C42	0.041 (3)	0.091 (4)	0.033 (3)	−0.020 (3)	0.001 (2)	−0.009 (3)
C43	0.035 (3)	0.073 (4)	0.038 (3)	−0.002 (3)	0.000 (2)	0.013 (3)
C44	0.031 (2)	0.037 (3)	0.045 (3)	−0.006 (2)	0.010 (2)	0.002 (2)
C45	0.026 (2)	0.043 (3)	0.035 (3)	−0.0025 (19)	0.0033 (19)	−0.005 (2)
C46	0.036 (2)	0.045 (3)	0.028 (2)	0.002 (2)	0.0024 (19)	−0.005 (2)
C47	0.107 (3)	0.087 (3)	0.066 (2)	−0.057 (2)	−0.012 (2)	0.0037 (19)
C48	0.086 (5)	0.082 (4)	0.047 (3)	−0.047 (4)	−0.021 (3)	0.001 (3)
C49	0.107 (3)	0.087 (3)	0.066 (2)	−0.057 (2)	−0.012 (2)	0.0037 (19)
C50	0.107 (3)	0.087 (3)	0.066 (2)	−0.057 (2)	−0.012 (2)	0.0037 (19)
C51	0.047 (3)	0.040 (3)	0.055 (3)	−0.018 (2)	0.013 (2)	−0.009 (2)
C52	0.036 (3)	0.027 (2)	0.075 (4)	−0.002 (2)	−0.008 (2)	0.000 (2)
C53	0.025 (2)	0.028 (2)	0.029 (2)	−0.0046 (18)	−0.0038 (18)	0.0010 (18)
C54	0.035 (2)	0.035 (3)	0.036 (3)	−0.005 (2)	0.000 (2)	−0.001 (2)
C55	0.031 (2)	0.043 (3)	0.039 (3)	0.000 (2)	0.003 (2)	−0.012 (2)
C56	0.024 (2)	0.056 (3)	0.042 (3)	−0.007 (2)	0.002 (2)	−0.018 (2)
C57	0.046 (3)	0.051 (3)	0.034 (3)	−0.025 (2)	0.010 (2)	0.000 (2)
C58	0.033 (2)	0.033 (2)	0.036 (3)	−0.0073 (19)	−0.002 (2)	−0.0010 (19)
C59	0.020 (2)	0.035 (2)	0.028 (2)	−0.0019 (17)	0.0043 (17)	−0.0024 (18)
C60	0.042 (3)	0.034 (3)	0.038 (3)	−0.007 (2)	0.000 (2)	−0.001 (2)
C61	0.053 (3)	0.035 (3)	0.051 (3)	−0.011 (2)	−0.001 (2)	−0.005 (2)
C62	0.034 (3)	0.045 (3)	0.055 (3)	−0.006 (2)	0.008 (2)	−0.026 (2)
C63	0.037 (3)	0.061 (3)	0.036 (3)	−0.014 (2)	−0.002 (2)	−0.010 (2)
C64	0.035 (3)	0.038 (3)	0.035 (3)	−0.011 (2)	0.000 (2)	−0.005 (2)
N1	0.0219 (18)	0.0280 (19)	0.042 (2)	−0.0053 (14)	0.0026 (15)	−0.0061 (16)
N2	0.0212 (17)	0.0284 (19)	0.0295 (19)	−0.0034 (14)	0.0006 (14)	−0.0024 (15)
N3	0.0236 (18)	0.0324 (19)	0.0261 (18)	−0.0091 (15)	−0.0008 (14)	0.0001 (14)
N4	0.0255 (19)	0.037 (2)	0.039 (2)	−0.0082 (16)	−0.0056 (16)	−0.0048 (16)
N5	0.0280 (18)	0.033 (2)	0.0255 (18)	−0.0113 (15)	−0.0027 (15)	0.0049 (15)
N6	0.0292 (19)	0.030 (2)	0.033 (2)	−0.0058 (15)	−0.0048 (15)	0.0046 (15)
O1	0.0366 (17)	0.0317 (16)	0.0295 (16)	−0.0009 (13)	0.0054 (13)	−0.0058 (13)
O2	0.0262 (15)	0.0413 (17)	0.0291 (16)	−0.0158 (13)	−0.0043 (12)	0.0012 (13)
O3	0.0325 (16)	0.0274 (16)	0.0421 (17)	−0.0084 (13)	−0.0047 (13)	0.0008 (13)
O4	0.051 (2)	0.044 (2)	0.0422 (19)	−0.0095 (16)	0.0046 (16)	0.0004 (16)
O5	0.051 (2)	0.043 (2)	0.044 (2)	−0.0147 (16)	−0.0035 (16)	0.0007 (15)
O6	0.0334 (17)	0.0501 (19)	0.0288 (16)	−0.0142 (14)	−0.0036 (13)	0.0088 (14)
O7	0.0225 (15)	0.0445 (18)	0.0319 (16)	−0.0092 (13)	−0.0038 (12)	0.0099 (13)
O8	0.0289 (16)	0.0456 (18)	0.0298 (16)	0.0056 (13)	−0.0024 (13)	−0.0061 (13)
O9	0.0270 (16)	0.068 (2)	0.0390 (19)	−0.0145 (15)	0.0045 (14)	−0.0121 (16)
O10	0.0278 (17)	0.053 (2)	0.0319 (17)	0.0039 (14)	−0.0061 (13)	−0.0094 (14)
O11	0.050 (2)	0.059 (2)	0.0338 (18)	−0.0275 (17)	0.0051 (15)	−0.0112 (15)
O12	0.107 (4)	0.105 (4)	0.064 (3)	−0.066 (3)	−0.025 (3)	0.032 (3)
O13	0.047 (2)	0.0448 (19)	0.055 (2)	−0.0160 (16)	−0.0053 (17)	0.0049 (16)
O14	0.0465 (19)	0.0353 (18)	0.0368 (18)	−0.0170 (15)	−0.0062 (15)	0.0074 (14)
P1	0.0245 (6)	0.0286 (6)	0.0306 (6)	−0.0040 (4)	−0.0002 (4)	−0.0023 (5)
P2	0.0200 (5)	0.0322 (6)	0.0289 (6)	−0.0064 (4)	−0.0020 (4)	0.0012 (5)
P3	0.0204 (5)	0.0292 (6)	0.0252 (6)	−0.0043 (4)	−0.0008 (4)	0.0011 (4)
P4	0.0251 (6)	0.0359 (7)	0.0287 (6)	−0.0022 (5)	−0.0040 (5)	−0.0036 (5)
P5	0.0275 (6)	0.0365 (7)	0.0288 (6)	−0.0111 (5)	0.0000 (5)	−0.0009 (5)
P6	0.0232 (5)	0.0305 (6)	0.0262 (6)	−0.0055 (4)	−0.0012 (4)	0.0006 (4)

Geometric parameters (Å, º) top

C1—C6	1.364 (6)	C37—H37	0.9500
C1—C2	1.382 (6)	C38—H38	0.9500
C1—O1	1.384 (5)	C39—C44	1.367 (6)
C2—C3	1.379 (7)	C39—O9	1.402 (5)
C2—H2	0.9500	C39—C40	1.378 (6)
C3—C4	1.355 (8)	C40—C41	1.393 (7)
C3—H3	0.9500	C40—H40	0.9500
C4—C5	1.382 (8)	C41—C42	1.379 (8)
C4—H4	0.9500	C41—H41	0.9500
C5—C6	1.391 (7)	C42—C43	1.365 (8)
C5—H5	0.9500	C42—H42	0.9500
C6—H6	0.9500	C43—C44	1.351 (7)
C7—C8	1.363 (6)	C43—H43	0.9500
C7—C12	1.391 (6)	C44—H44	0.97 (5)
C7—O2	1.405 (5)	C45—O10	1.452 (5)
C8—C9	1.389 (7)	C45—C46	1.491 (6)
C8—H8	0.9500	C45—H45A	0.9900
C9—C10	1.374 (7)	C45—H45B	0.9900
C9—H9	0.9500	C46—O11	1.399 (6)
C10—C11	1.357 (7)	C46—H46A	0.9900
C10—H10	0.9500	C46—H46B	0.9900
C11—C12	1.388 (6)	C47—O11	1.422 (7)
C11—H11	0.9500	C47—C48	1.497 (8)
C12—H12	0.9500	C47—H47A	0.9900
C13—O3	1.432 (5)	C47—H47B	0.9900
C13—C14	1.495 (6)	C48—O12	1.428 (7)
C13—H13A	0.9900	C48—H48A	0.9900
C13—H13B	0.9900	C48—H48B	0.9900
C14—O4	1.415 (5)	C49—C50	1.5378 (11)
C14—H14A	0.9900	C49—O12	1.394 (7)
C14—H14B	0.9900	C49—H49A	0.9900
C15—O4	1.419 (6)	C49—H49B	0.9900
C15—C16	1.448 (8)	C50—O13	1.394 (7)
C15—H15A	0.9900	C50—H50A	0.9900
C15—H15B	0.9900	C50—H50B	0.9900
C16—O5	1.426 (6)	C51—O13	1.421 (5)
C16—H16A	0.9900	C51—C52	1.508 (7)
C16—H16B	0.9900	C51—H51A	0.9900
C17—O5	1.410 (6)	C51—H51B	0.9900
C17—C18	1.467 (7)	C52—O14	1.444 (6)
C17—H17A	0.9900	C52—H52A	0.9900
C17—H17B	0.9900	C52—H52B	0.9900
C18—O6	1.442 (5)	C53—C54	1.376 (6)
C18—H18A	0.9900	C53—C58	1.392 (6)
C18—H18B	0.9900	C53—P6	1.808 (4)
C19—O6	1.413 (5)	C54—C55	1.376 (6)
C19—C20	1.506 (6)	C54—H54	0.9500
C19—H19A	0.9900	C55—C56	1.376 (7)
C19—H19B	0.9900	C55—H55	0.9500
C20—O7	1.462 (5)	C56—C57	1.381 (7)
C20—H20A	0.9900	C56—H56	0.97 (5)
C20—H20B	0.9900	C57—C58	1.370 (6)
C21—C22	1.378 (6)	C57—H57	0.9500
C21—C26	1.401 (6)	C58—H58	0.9500
C21—P3	1.804 (4)	C59—C60	1.388 (6)
C22—C23	1.387 (6)	C59—C64	1.388 (6)
C22—H22	0.9500	C59—P6	1.798 (4)
C23—C24	1.390 (7)	C60—C61	1.390 (7)
C23—H23	0.9500	C60—H60	0.98 (4)
C24—C25	1.382 (7)	C61—C62	1.366 (7)
C24—H24	0.9500	C61—H61	0.9500
C25—C26	1.383 (6)	C62—C63	1.390 (7)
C25—H25	0.95 (4)	C62—H62	0.9500
C26—H26	0.9500	C63—C64	1.384 (6)
C27—C28	1.381 (6)	C63—H63	0.9500
C27—C32	1.398 (6)	C64—H64	0.9500
C27—P3	1.795 (4)	N1—P1	1.574 (4)
C28—C29	1.394 (6)	N1—P2	1.585 (4)
C28—H28	1.04 (3)	N2—P2	1.577 (3)
C29—C30	1.368 (7)	N2—P3	1.602 (3)
C29—H29	0.9500	N3—P1	1.585 (3)
C30—C31	1.385 (7)	N3—P3	1.605 (3)
C30—H30	0.9500	N4—P5	1.569 (3)
C31—C32	1.399 (6)	N4—P4	1.584 (4)
C31—H31	0.9500	N5—P5	1.575 (3)
C32—H32	0.9500	N5—P6	1.602 (3)
C33—C38	1.361 (6)	N6—P4	1.574 (4)
C33—C34	1.379 (6)	N6—P6	1.606 (3)
C33—O8	1.402 (5)	O1—P1	1.602 (3)
C34—C35	1.407 (7)	O2—P2	1.591 (3)
C34—H34	0.9500	O3—P1	1.576 (3)
C35—C36	1.377 (8)	O7—P2	1.578 (3)
C35—H35	1.15 (5)	O8—P4	1.595 (3)
C36—C37	1.362 (7)	O9—P5	1.596 (3)
C36—H36	0.9500	O10—P4	1.580 (3)
C37—C38	1.400 (7)	O14—P5	1.565 (3)

C6—C1—C2	120.5 (4)	C43—C42—H42	120.5
C6—C1—O1	120.6 (4)	C41—C42—H42	120.5
C2—C1—O1	118.8 (4)	C44—C43—C42	121.5 (5)
C1—C2—C3	119.9 (5)	C44—C43—H43	119.2
C1—C2—H2	120.0	C42—C43—H43	119.2
C3—C2—H2	120.0	C43—C44—C39	119.6 (5)
C4—C3—C2	119.9 (5)	C43—C44—H44	121 (3)
C4—C3—H3	120.1	C39—C44—H44	120 (3)
C2—C3—H3	120.1	O10—C45—C46	107.4 (3)
C3—C4—C5	120.6 (5)	O10—C45—H45A	110.2
C3—C4—H4	119.7	C46—C45—H45A	110.2
C5—C4—H4	119.7	O10—C45—H45B	110.2
C4—C5—C6	119.8 (5)	C46—C45—H45B	110.2
C4—C5—H5	120.1	H45A—C45—H45B	108.5
C6—C5—H5	120.1	O11—C46—C45	107.7 (4)
C1—C6—C5	119.2 (5)	O11—C46—H46A	110.2
C1—C6—H6	120.4	C45—C46—H46A	110.2
C5—C6—H6	120.4	O11—C46—H46B	110.2
C8—C7—C12	121.5 (4)	C45—C46—H46B	110.2
C8—C7—O2	118.0 (4)	H46A—C46—H46B	108.5
C12—C7—O2	120.5 (4)	O11—C47—C48	108.0 (5)
C7—C8—C9	118.9 (4)	O11—C47—H47A	110.1
C7—C8—H8	120.6	C48—C47—H47A	110.1
C9—C8—H8	120.6	O11—C47—H47B	110.1
C10—C9—C8	121.0 (5)	C48—C47—H47B	110.1
C10—C9—H9	119.5	H47A—C47—H47B	108.4
C8—C9—H9	119.5	O12—C48—C47	106.7 (5)
C11—C10—C9	118.8 (5)	O12—C48—H48A	110.4
C11—C10—H10	120.6	C47—C48—H48A	110.4
C9—C10—H10	120.6	O12—C48—H48B	110.4
C10—C11—C12	122.3 (4)	C47—C48—H48B	110.4
C10—C11—H11	118.9	H48A—C48—H48B	108.6
C12—C11—H11	118.9	C50—C49—O12	109.8 (5)
C7—C12—C11	117.4 (4)	C50—C49—H49A	109.7
C7—C12—H12	121.3	O12—C49—H49A	109.7
C11—C12—H12	121.3	C50—C49—H49B	109.7
O3—C13—C14	108.3 (4)	O12—C49—H49B	109.7
O3—C13—H13A	110.0	H49A—C49—H49B	108.2
C14—C13—H13A	110.0	O13—C50—C49	121.0 (5)
O3—C13—H13B	110.0	O13—C50—H50A	107.1
C14—C13—H13B	110.0	C49—C50—H50A	107.1
H13A—C13—H13B	108.4	O13—C50—H50B	107.1
O4—C14—C13	108.7 (4)	C49—C50—H50B	107.1
O4—C14—H14A	110.0	H50A—C50—H50B	106.8
C13—C14—H14A	110.0	O13—C51—C52	108.7 (4)
O4—C14—H14B	110.0	O13—C51—H51A	110.0
C13—C14—H14B	110.0	C52—C51—H51A	110.0
H14A—C14—H14B	108.3	O13—C51—H51B	110.0
O4—C15—C16	110.5 (4)	C52—C51—H51B	110.0
O4—C15—H15A	109.6	H51A—C51—H51B	108.3
C16—C15—H15A	109.6	O14—C52—C51	112.7 (4)
O4—C15—H15B	109.6	O14—C52—H52A	109.1
C16—C15—H15B	109.6	C51—C52—H52A	109.1
H15A—C15—H15B	108.1	O14—C52—H52B	109.1
O5—C16—C15	110.1 (5)	C51—C52—H52B	109.1
O5—C16—H16A	109.6	H52A—C52—H52B	107.8
C15—C16—H16A	109.6	C54—C53—C58	118.6 (4)
O5—C16—H16B	109.6	C54—C53—P6	122.2 (3)
C15—C16—H16B	109.6	C58—C53—P6	119.2 (3)
H16A—C16—H16B	108.2	C53—C54—C55	121.0 (4)
O5—C17—C18	108.7 (4)	C53—C54—H54	119.5
O5—C17—H17A	109.9	C55—C54—H54	119.5
C18—C17—H17A	109.9	C56—C55—C54	120.3 (4)
O5—C17—H17B	109.9	C56—C55—H55	119.8
C18—C17—H17B	109.9	C54—C55—H55	119.8
H17A—C17—H17B	108.3	C55—C56—C57	118.9 (4)
O6—C18—C17	112.9 (4)	C55—C56—H56	123 (3)
O6—C18—H18A	109.0	C57—C56—H56	118 (3)
C17—C18—H18A	109.0	C58—C57—C56	121.1 (4)
O6—C18—H18B	109.0	C58—C57—H57	119.5
C17—C18—H18B	109.0	C56—C57—H57	119.5
H18A—C18—H18B	107.8	C57—C58—C53	120.1 (4)
O6—C19—C20	111.4 (4)	C57—C58—H58	120.0
O6—C19—H19A	109.3	C53—C58—H58	120.0
C20—C19—H19A	109.3	C60—C59—C64	119.5 (4)
O6—C19—H19B	109.3	C60—C59—P6	119.6 (3)
C20—C19—H19B	109.3	C64—C59—P6	120.9 (3)
H19A—C19—H19B	108.0	C59—C60—C61	120.4 (4)
O7—C20—C19	108.4 (4)	C59—C60—H60	118 (2)
O7—C20—H20A	110.0	C61—C60—H60	121 (2)
C19—C20—H20A	110.0	C62—C61—C60	119.7 (5)
O7—C20—H20B	110.0	C62—C61—H61	120.1
C19—C20—H20B	110.0	C60—C61—H61	120.1
H20A—C20—H20B	108.4	C61—C62—C63	120.5 (4)
C22—C21—C26	118.9 (4)	C61—C62—H62	119.7
C22—C21—P3	120.3 (3)	C63—C62—H62	119.7
C26—C21—P3	120.7 (3)	C64—C63—C62	120.0 (4)
C21—C22—C23	120.6 (4)	C64—C63—H63	120.0
C21—C22—H22	119.7	C62—C63—H63	120.0
C23—C22—H22	119.7	C63—C64—C59	119.8 (4)
C22—C23—C24	120.5 (4)	C63—C64—H64	120.1
C22—C23—H23	119.7	C59—C64—H64	120.1
C24—C23—H23	119.7	P1—N1—P2	122.5 (2)
C25—C24—C23	119.0 (4)	P2—N2—P3	122.9 (2)
C25—C24—H24	120.5	P1—N3—P3	120.8 (2)
C23—C24—H24	120.5	P5—N4—P4	122.3 (2)
C26—C25—C24	120.7 (5)	P5—N5—P6	120.4 (2)
C26—C25—H25	121 (2)	P4—N6—P6	122.5 (2)
C24—C25—H25	118 (2)	C1—O1—P1	122.2 (3)
C25—C26—C21	120.3 (5)	C7—O2—P2	122.7 (2)
C25—C26—H26	119.9	C13—O3—P1	120.9 (3)
C21—C26—H26	119.9	C15—O4—C14	113.2 (4)
C28—C27—C32	119.5 (4)	C17—O5—C16	110.7 (4)
C28—C27—P3	120.0 (3)	C19—O6—C18	114.9 (3)
C32—C27—P3	120.5 (3)	C20—O7—P2	118.7 (3)
C27—C28—C29	119.9 (5)	C33—O8—P4	121.0 (2)
C27—C28—H28	124.3 (17)	C39—O9—P5	122.5 (3)
C29—C28—H28	115.7 (17)	C45—O10—P4	118.8 (2)
C30—C29—C28	120.6 (5)	C46—O11—C47	112.8 (4)
C30—C29—H29	119.7	C49—O12—C48	117.5 (5)
C28—C29—H29	119.7	C50—O13—C51	117.4 (4)
C31—C30—C29	120.5 (4)	C52—O14—P5	118.3 (3)
C31—C30—H30	119.7	O3—P1—N1	105.96 (17)
C29—C30—H30	119.7	O3—P1—N3	112.27 (17)
C30—C31—C32	119.2 (5)	N1—P1—N3	118.50 (18)
C30—C31—H31	120.4	O3—P1—O1	98.76 (16)
C32—C31—H31	120.4	N1—P1—O1	110.71 (18)
C31—C32—C27	120.1 (4)	N3—P1—O1	108.84 (16)
C31—C32—H32	119.9	O7—P2—N1	112.01 (18)
C27—C32—H32	119.9	O7—P2—N2	110.43 (17)
C38—C33—C34	122.7 (4)	N1—P2—N2	116.76 (18)
C38—C33—O8	118.9 (4)	O7—P2—O2	94.59 (15)
C34—C33—O8	118.3 (4)	N1—P2—O2	109.31 (17)
C33—C34—C35	117.4 (5)	N2—P2—O2	111.56 (17)
C33—C34—H34	121.3	N3—P3—N2	117.30 (17)
C35—C34—H34	121.3	N3—P3—C27	108.53 (19)
C36—C35—C34	120.7 (5)	N2—P3—C27	108.41 (19)
C36—C35—H35	119 (2)	N3—P3—C21	107.34 (19)
C34—C35—H35	120 (2)	N2—P3—C21	108.66 (18)
C37—C36—C35	120.0 (5)	C27—P3—C21	106.04 (18)
C37—C36—H36	120.0	O10—P4—N6	110.86 (18)
C35—C36—H36	120.0	O10—P4—N4	111.54 (19)
C36—C37—C38	120.6 (5)	N6—P4—N4	116.97 (18)
C36—C37—H37	119.7	O10—P4—O8	94.06 (15)
C38—C37—H37	119.7	N6—P4—O8	111.30 (18)
C33—C38—C37	118.5 (5)	N4—P4—O8	109.79 (18)
C33—C38—H38	120.7	O14—P5—N4	110.20 (18)
C37—C38—H38	120.7	O14—P5—N5	109.64 (18)
C44—C39—O9	122.3 (4)	N4—P5—N5	117.69 (19)
C44—C39—C40	121.2 (4)	O14—P5—O9	100.10 (18)
O9—C39—C40	116.4 (4)	N4—P5—O9	106.06 (18)
C41—C40—C39	118.0 (4)	N5—P5—O9	111.69 (18)
C41—C40—H40	121.0	N5—P6—N6	117.01 (18)
C39—C40—H40	121.0	N5—P6—C59	109.39 (18)
C42—C41—C40	120.6 (5)	N6—P6—C59	107.65 (19)
C42—C41—H41	119.7	N5—P6—C53	109.10 (18)
C40—C41—H41	119.7	N6—P6—C53	108.32 (18)
C43—C42—C41	119.0 (5)	C59—P6—C53	104.67 (19)

C6—C1—C2—C3	2.0 (7)	C48—C47—O11—C46	173.0 (5)
O1—C1—C2—C3	179.5 (4)	C50—C49—O12—C48	−91.5 (7)
C1—C2—C3—C4	−0.7 (8)	C47—C48—O12—C49	173.3 (5)
C2—C3—C4—C5	−0.5 (8)	C49—C50—O13—C51	60.8 (7)
C3—C4—C5—C6	0.6 (8)	C52—C51—O13—C50	166.8 (4)
C2—C1—C6—C5	−1.9 (7)	C51—C52—O14—P5	−95.0 (4)
O1—C1—C6—C5	−179.4 (4)	C13—O3—P1—N1	179.2 (3)
C4—C5—C6—C1	0.7 (8)	C13—O3—P1—N3	−50.0 (3)
C12—C7—C8—C9	−1.6 (7)	C13—O3—P1—O1	64.6 (3)
O2—C7—C8—C9	176.4 (4)	P2—N1—P1—O3	114.2 (3)
C7—C8—C9—C10	2.8 (8)	P2—N1—P1—N3	−12.9 (3)
C8—C9—C10—C11	−2.0 (8)	P2—N1—P1—O1	−139.7 (2)
C9—C10—C11—C12	0.1 (8)	P3—N3—P1—O3	−117.6 (2)
C8—C7—C12—C11	−0.2 (7)	P3—N3—P1—N1	6.5 (3)
O2—C7—C12—C11	−178.2 (4)	P3—N3—P1—O1	134.2 (2)
C10—C11—C12—C7	1.0 (7)	C1—O1—P1—O3	−150.1 (3)
O3—C13—C14—O4	−69.7 (5)	C1—O1—P1—N1	99.0 (3)
O4—C15—C16—O5	69.1 (6)	C1—O1—P1—N3	−32.9 (4)
O5—C17—C18—O6	70.3 (5)	C20—O7—P2—N1	81.6 (3)
O6—C19—C20—O7	174.5 (3)	C20—O7—P2—N2	−50.4 (3)
C26—C21—C22—C23	−1.3 (6)	C20—O7—P2—O2	−165.4 (3)
P3—C21—C22—C23	−178.6 (3)	P1—N1—P2—O7	−118.1 (2)
C21—C22—C23—C24	0.7 (7)	P1—N1—P2—N2	10.6 (3)
C22—C23—C24—C25	0.3 (7)	P1—N1—P2—O2	138.4 (2)
C23—C24—C25—C26	−0.7 (7)	P3—N2—P2—O7	127.4 (2)
C24—C25—C26—C21	0.1 (7)	P3—N2—P2—N1	−2.0 (3)
C22—C21—C26—C25	1.0 (6)	P3—N2—P2—O2	−128.7 (2)
P3—C21—C26—C25	178.2 (3)	C7—O2—P2—O7	−172.5 (3)
C32—C27—C28—C29	2.0 (6)	C7—O2—P2—N1	−57.2 (3)
P3—C27—C28—C29	−177.9 (3)	C7—O2—P2—N2	73.4 (3)
C27—C28—C29—C30	−0.1 (7)	P1—N3—P3—N2	1.4 (3)
C28—C29—C30—C31	−1.4 (7)	P1—N3—P3—C27	−121.8 (2)
C29—C30—C31—C32	1.1 (7)	P1—N3—P3—C21	124.0 (2)
C30—C31—C32—C27	0.8 (7)	P2—N2—P3—N3	−3.7 (3)
C28—C27—C32—C31	−2.3 (6)	P2—N2—P3—C27	119.6 (2)
P3—C27—C32—C31	177.6 (3)	P2—N2—P3—C21	−125.6 (2)
C38—C33—C34—C35	−1.1 (7)	C28—C27—P3—N3	−11.4 (4)
O8—C33—C34—C35	174.8 (4)	C32—C27—P3—N3	168.7 (3)
C33—C34—C35—C36	0.8 (7)	C28—C27—P3—N2	−139.9 (3)
C34—C35—C36—C37	−0.1 (7)	C32—C27—P3—N2	40.3 (4)
C35—C36—C37—C38	−0.5 (7)	C28—C27—P3—C21	103.6 (4)
C34—C33—C38—C37	0.5 (6)	C32—C27—P3—C21	−76.3 (4)
O8—C33—C38—C37	−175.4 (3)	C22—C21—P3—N3	−15.3 (4)
C36—C37—C38—C33	0.3 (7)	C26—C21—P3—N3	167.5 (3)
C44—C39—C40—C41	0.8 (7)	C22—C21—P3—N2	112.5 (3)
O9—C39—C40—C41	179.5 (4)	C26—C21—P3—N2	−64.7 (3)
C39—C40—C41—C42	0.5 (7)	C22—C21—P3—C27	−131.2 (3)
C40—C41—C42—C43	−0.7 (8)	C26—C21—P3—C27	51.6 (4)
C41—C42—C43—C44	−0.3 (8)	C45—O10—P4—N6	54.8 (4)
C42—C43—C44—C39	1.6 (7)	C45—O10—P4—N4	−77.5 (3)
O9—C39—C44—C43	179.6 (4)	C45—O10—P4—O8	169.4 (3)
C40—C39—C44—C43	−1.8 (7)	P6—N6—P4—O10	−125.7 (2)
O10—C45—C46—O11	−67.7 (4)	P6—N6—P4—N4	3.7 (3)
O11—C47—C48—O12	−68.9 (7)	P6—N6—P4—O8	131.0 (2)
O12—C49—C50—O13	−67.9 (8)	P5—N4—P4—O10	136.0 (2)
O13—C51—C52—O14	−71.4 (5)	P5—N4—P4—N6	7.0 (3)
C58—C53—C54—C55	0.8 (6)	P5—N4—P4—O8	−121.1 (2)
P6—C53—C54—C55	−177.8 (3)	C33—O8—P4—O10	168.8 (3)
C53—C54—C55—C56	0.5 (7)	C33—O8—P4—N6	−76.9 (4)
C54—C55—C56—C57	−1.3 (7)	C33—O8—P4—N4	54.2 (4)
C55—C56—C57—C58	0.9 (7)	C52—O14—P5—N4	69.9 (3)
C56—C57—C58—C53	0.3 (7)	C52—O14—P5—N5	−61.1 (3)
C54—C53—C58—C57	−1.2 (6)	C52—O14—P5—O9	−178.6 (3)
P6—C53—C58—C57	177.4 (3)	P4—N4—P5—O14	−145.8 (2)
C64—C59—C60—C61	0.7 (7)	P4—N4—P5—N5	−19.1 (3)
P6—C59—C60—C61	−179.3 (4)	P4—N4—P5—O9	106.7 (3)
C59—C60—C61—C62	0.1 (7)	P6—N5—P5—O14	147.8 (2)
C60—C61—C62—C63	−1.5 (7)	P6—N5—P5—N4	20.8 (3)
C61—C62—C63—C64	2.1 (7)	P6—N5—P5—O9	−102.2 (3)
C62—C63—C64—C59	−1.3 (7)	C39—O9—P5—O14	92.9 (3)
C60—C59—C64—C63	−0.1 (6)	C39—O9—P5—N4	−152.5 (3)
P6—C59—C64—C63	179.9 (3)	C39—O9—P5—N5	−23.1 (4)
C6—C1—O1—P1	−72.7 (5)	P5—N5—P6—N6	−10.7 (3)
C2—C1—O1—P1	109.8 (4)	P5—N5—P6—C59	112.0 (3)
C8—C7—O2—P2	116.6 (4)	P5—N5—P6—C53	−134.0 (2)
C12—C7—O2—P2	−65.4 (5)	P4—N6—P6—N5	−1.8 (3)
C14—C13—O3—P1	156.1 (3)	P4—N6—P6—C59	−125.4 (3)
C16—C15—O4—C14	−179.3 (4)	P4—N6—P6—C53	121.9 (3)
C13—C14—O4—C15	143.1 (4)	C60—C59—P6—N5	−159.0 (3)
C18—C17—O5—C16	173.7 (4)	C64—C59—P6—N5	21.0 (4)
C15—C16—O5—C17	−178.9 (4)	C60—C59—P6—N6	−30.9 (4)
C20—C19—O6—C18	83.6 (4)	C64—C59—P6—N6	149.1 (3)
C17—C18—O6—C19	−123.4 (4)	C60—C59—P6—C53	84.2 (4)
C19—C20—O7—P2	104.7 (3)	C64—C59—P6—C53	−95.8 (4)
C38—C33—O8—P4	−102.3 (4)	C54—C53—P6—N5	−12.8 (4)
C34—C33—O8—P4	81.7 (4)	C58—C53—P6—N5	168.6 (3)
C44—C39—O9—P5	−62.6 (5)	C54—C53—P6—N6	−141.2 (4)
C40—C39—O9—P5	118.7 (4)	C58—C53—P6—N6	40.3 (4)
C46—C45—O10—P4	152.5 (3)	C54—C53—P6—C59	104.1 (4)
C45—C46—O11—C47	−169.7 (4)	C58—C53—P6—C59	−74.4 (4)

(6) top

Crystal data top

C₂₂H₃₂N₃O₇P₃	F(000) = 1144
M_r = 543.42	D_x = 1.387 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.8293 (2) Å	Cell parameters from 8163 reflections
b = 10.3312 (2) Å	θ = 2.9–27.5°
c = 21.6318 (5) Å	µ = 0.28 mm⁻¹
β = 100.203 (1)°	T = 293 K
V = 2601.84 (9) Å³	Plate, colourless
Z = 4	0.26 × 0.20 × 0.07 mm

Data collection top

Nonius KappaCCD diffractometer	5841 independent reflections
Radiation source: Nonius FR591 rotating anode	4160 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ϕ & ω scans	h = −14→15
Absorption correction: multi-scan SORTAV (Blessing, 1997)	k = −12→13
T_min = 0.932, T_max = 0.981	l = −27→28
18814 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0776P)² + 1.3016P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.061
5841 reflections	Δρ_max = 0.46 e Å⁻³
319 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0061 (11)

Crystal data top

C₂₂H₃₂N₃O₇P₃	V = 2601.84 (9) Å³
M_r = 543.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8293 (2) Å	µ = 0.28 mm⁻¹
b = 10.3312 (2) Å	T = 293 K
c = 21.6318 (5) Å	0.26 × 0.20 × 0.07 mm
β = 100.203 (1)°

Data collection top

Nonius KappaCCD diffractometer	5841 independent reflections
Absorption correction: multi-scan SORTAV (Blessing, 1997)	4160 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.981	R_int = 0.038
18814 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.00	Δρ_max = 0.46 e Å⁻³
5841 reflections	Δρ_min = −0.31 e Å⁻³
319 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.3021 (3)	0.9455 (3)	0.21276 (16)	0.0714 (9)
H1A	0.2981	0.8961	0.1749	0.107*
H1B	0.2902	0.8893	0.2464	0.107*
H1C	0.3763	0.9855	0.2231	0.107*
C2	0.3682 (4)	0.8899 (3)	0.03540 (18)	0.0891 (12)
H2A	0.4067	0.9156	0.0764	0.134*
H2B	0.4220	0.8485	0.0134	0.134*
H2C	0.3073	0.8307	0.0394	0.134*
C3	−0.0040 (2)	1.1653 (3)	0.14186 (16)	0.0641 (8)
H3A	−0.0143	1.1051	0.1748	0.077*
H3B	−0.0081	1.1172	0.1030	0.077*
C4	−0.0954 (3)	1.2645 (4)	0.1345 (2)	0.0875 (12)
H4A	−0.1695	1.2237	0.1337	0.105*
H4B	−0.0819	1.3243	0.1696	0.105*
C5	−0.1946 (4)	1.4066 (5)	0.0588 (3)	0.1176 (19)
H5A	−0.2036	1.4676	0.0916	0.141*
H5B	−0.2615	1.3506	0.0515	0.141*
C6	−0.1849 (4)	1.4771 (5)	0.0004 (3)	0.127 (2)
H6A	−0.2529	1.5297	−0.0125	0.152*
H6B	−0.1187	1.5341	0.0080	0.152*
C7	−0.1367 (4)	1.4515 (5)	−0.0980 (3)	0.123 (2)
H7A	−0.0759	1.5125	−0.0827	0.148*
H7B	−0.2002	1.4988	−0.1224	0.148*
C8	−0.0949 (4)	1.3538 (6)	−0.1374 (2)	0.125 (2)
H8A	−0.1514	1.2851	−0.1454	0.150*
H8B	−0.0892	1.3931	−0.1774	0.150*
C9	0.0084 (3)	1.2023 (4)	−0.06467 (19)	0.0818 (10)
H9A	−0.0580	1.1472	−0.0775	0.098*
H9B	0.0001	1.2446	−0.0257	0.098*
C10	0.1109 (3)	1.1247 (3)	−0.05482 (17)	0.0753 (9)
H10A	0.1258	1.0950	−0.0952	0.090*
H10B	0.0985	1.0490	−0.0303	0.090*
C11	0.5464 (2)	1.1787 (2)	0.17236 (12)	0.0447 (6)
C12	0.5809 (3)	1.2011 (3)	0.23638 (15)	0.0684 (8)
H12	0.5436	1.2639	0.2562	0.082*
C13	0.6699 (3)	1.1310 (4)	0.27077 (19)	0.0860 (11)
H13	0.6922	1.1469	0.3135	0.103*
C14	0.7255 (3)	1.0382 (4)	0.2423 (2)	0.0840 (11)
H14	0.7850	0.9907	0.2657	0.101*
C15	0.6930 (3)	1.0158 (3)	0.1795 (2)	0.0780 (10)
H15	0.7308	0.9526	0.1603	0.094*
C16	0.6036 (2)	1.0867 (3)	0.14346 (15)	0.0596 (7)
H16	0.5831	1.0717	0.1005	0.072*
C17	0.4622 (2)	1.4311 (2)	0.13249 (11)	0.0423 (5)
C18	0.4390 (2)	1.5125 (3)	0.17955 (14)	0.0555 (7)
H18	0.4000	1.4810	0.2101	0.067*
C19	0.4737 (3)	1.6402 (3)	0.18127 (17)	0.0706 (9)
H19	0.4577	1.6944	0.2129	0.085*
C20	0.5314 (3)	1.6870 (3)	0.13685 (18)	0.0734 (9)
H20	0.5546	1.7731	0.1385	0.088*
C21	0.5554 (3)	1.6088 (3)	0.09003 (17)	0.0726 (9)
H21	0.5952	1.6415	0.0600	0.087*
C22	0.5202 (2)	1.4797 (3)	0.08718 (14)	0.0572 (7)
H22	0.5356	1.4265	0.0550	0.069*
N1	0.2112 (2)	1.0827 (2)	0.08603 (10)	0.0485 (5)
N2	0.39368 (18)	1.2137 (2)	0.05984 (9)	0.0462 (5)
N3	0.32212 (17)	1.2480 (2)	0.17228 (9)	0.0431 (5)
O1	0.21493 (17)	1.04370 (18)	0.20364 (8)	0.0562 (5)
O2	0.3218 (2)	1.00054 (18)	0.00146 (9)	0.0650 (6)
O4	−0.0948 (2)	1.3320 (3)	0.07766 (15)	0.0915 (8)
O5	−0.1734 (2)	1.3896 (3)	−0.04690 (16)	0.0980 (9)
O6	0.0136 (2)	1.2976 (3)	−0.11189 (13)	0.0977 (9)
O7	0.21093 (17)	1.19435 (19)	−0.02255 (8)	0.0565 (5)
O3	0.10657 (14)	1.22816 (17)	0.15776 (9)	0.0500 (4)
P1	0.21922 (5)	1.15158 (6)	0.15205 (3)	0.04093 (18)
P2	0.28683 (6)	1.12480 (6)	0.03577 (3)	0.04374 (19)
P3	0.42139 (5)	1.26306 (6)	0.13107 (3)	0.03865 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.093 (2)	0.0566 (17)	0.0664 (19)	0.0088 (17)	0.0186 (17)	0.0190 (15)
C2	0.138 (4)	0.0580 (19)	0.078 (2)	0.028 (2)	0.038 (2)	0.0070 (17)
C3	0.0464 (15)	0.0665 (19)	0.079 (2)	−0.0168 (14)	0.0105 (14)	−0.0009 (16)
C4	0.0464 (18)	0.104 (3)	0.116 (3)	−0.0064 (18)	0.0236 (19)	−0.005 (3)
C5	0.069 (2)	0.120 (4)	0.148 (4)	0.045 (3)	−0.021 (3)	−0.047 (4)
C6	0.105 (4)	0.084 (3)	0.163 (5)	0.033 (3)	−0.050 (4)	−0.024 (3)
C7	0.068 (2)	0.104 (3)	0.190 (6)	0.010 (2)	0.000 (3)	0.069 (4)
C8	0.080 (3)	0.182 (6)	0.104 (4)	0.026 (3)	−0.007 (3)	0.062 (4)
C9	0.068 (2)	0.081 (2)	0.094 (3)	−0.0098 (19)	0.0084 (19)	0.011 (2)
C10	0.075 (2)	0.076 (2)	0.066 (2)	−0.0119 (18)	−0.0112 (17)	−0.0049 (17)
C11	0.0417 (12)	0.0418 (13)	0.0516 (14)	−0.0029 (11)	0.0107 (11)	0.0053 (11)
C12	0.0679 (19)	0.0704 (19)	0.0599 (18)	0.0136 (16)	−0.0081 (15)	−0.0015 (15)
C13	0.079 (2)	0.091 (3)	0.076 (2)	0.010 (2)	−0.0186 (19)	0.010 (2)
C14	0.0554 (19)	0.075 (2)	0.114 (3)	0.0091 (17)	−0.004 (2)	0.025 (2)
C15	0.0581 (18)	0.0576 (19)	0.123 (3)	0.0151 (16)	0.029 (2)	0.007 (2)
C16	0.0533 (16)	0.0562 (16)	0.0727 (19)	0.0017 (13)	0.0203 (14)	−0.0010 (14)
C17	0.0396 (12)	0.0427 (13)	0.0442 (13)	0.0020 (10)	0.0060 (10)	0.0020 (10)
C18	0.0610 (17)	0.0497 (15)	0.0563 (16)	0.0018 (13)	0.0112 (13)	−0.0051 (12)
C19	0.087 (2)	0.0439 (16)	0.077 (2)	0.0054 (15)	0.0024 (18)	−0.0079 (14)
C20	0.080 (2)	0.0395 (15)	0.092 (3)	−0.0055 (15)	−0.0072 (19)	0.0068 (16)
C21	0.072 (2)	0.0608 (19)	0.086 (2)	−0.0116 (16)	0.0170 (17)	0.0233 (17)
C22	0.0599 (17)	0.0519 (15)	0.0631 (17)	−0.0024 (13)	0.0198 (14)	0.0052 (13)
N1	0.0601 (13)	0.0423 (11)	0.0450 (12)	−0.0118 (10)	0.0141 (10)	−0.0056 (9)
N2	0.0484 (12)	0.0540 (12)	0.0380 (11)	−0.0049 (10)	0.0129 (9)	−0.0030 (9)
N3	0.0423 (11)	0.0517 (12)	0.0370 (10)	−0.0070 (9)	0.0119 (8)	−0.0064 (9)
O1	0.0709 (12)	0.0512 (10)	0.0519 (11)	−0.0029 (9)	0.0252 (9)	0.0110 (9)
O2	0.0995 (16)	0.0461 (10)	0.0537 (11)	0.0075 (11)	0.0256 (11)	−0.0072 (9)
O4	0.0530 (13)	0.0855 (17)	0.132 (2)	0.0085 (12)	0.0061 (14)	0.0093 (16)
O5	0.0861 (18)	0.0715 (16)	0.132 (2)	0.0000 (14)	0.0078 (17)	0.0082 (17)
O6	0.0673 (15)	0.130 (2)	0.0927 (19)	0.0112 (15)	0.0065 (13)	0.0477 (17)
O7	0.0669 (12)	0.0533 (11)	0.0442 (10)	−0.0085 (9)	−0.0042 (9)	0.0044 (8)
O3	0.0386 (9)	0.0487 (10)	0.0639 (11)	−0.0058 (8)	0.0124 (8)	−0.0102 (8)
P1	0.0455 (4)	0.0388 (3)	0.0404 (3)	−0.0047 (3)	0.0129 (3)	−0.0006 (2)
P2	0.0569 (4)	0.0390 (3)	0.0360 (3)	−0.0024 (3)	0.0100 (3)	−0.0030 (2)
P3	0.0391 (3)	0.0416 (3)	0.0364 (3)	−0.0016 (3)	0.0097 (2)	−0.0011 (2)

Geometric parameters (Å, º) top

C1—O1	1.435 (4)	C10—H10B	0.9700
C1—H1A	0.9600	C11—C16	1.379 (4)
C1—H1B	0.9600	C11—C12	1.392 (4)
C1—H1C	0.9600	C11—P3	1.810 (3)
C2—O2	1.415 (4)	C12—C13	1.382 (5)
C2—H2A	0.9600	C12—H12	0.9300
C2—H2B	0.9600	C13—C14	1.369 (6)
C2—H2C	0.9600	C13—H13	0.9300
C3—O3	1.446 (3)	C14—C15	1.365 (6)
C3—C4	1.477 (5)	C14—H14	0.9300
C3—H3A	0.9700	C15—C16	1.404 (5)
C3—H3B	0.9700	C15—H15	0.9300
C4—O4	1.415 (5)	C16—H16	0.9300
C4—H4A	0.9700	C17—C22	1.387 (4)
C4—H4B	0.9700	C17—C18	1.385 (4)
C5—O4	1.408 (4)	C17—P3	1.800 (3)
C5—C6	1.480 (8)	C18—C19	1.380 (4)
C5—H5A	0.9700	C18—H18	0.9300
C5—H5B	0.9700	C19—C20	1.362 (5)
C6—O5	1.390 (6)	C19—H19	0.9300
C6—H6A	0.9700	C20—C21	1.364 (5)
C6—H6B	0.9700	C20—H20	0.9300
C7—O5	1.409 (6)	C21—C22	1.395 (4)
C7—C8	1.463 (8)	C21—H21	0.9300
C7—H7A	0.9700	C22—H22	0.9300
C7—H7B	0.9700	N1—P1	1.583 (2)
C8—O6	1.427 (5)	N1—P2	1.586 (2)
C8—H8A	0.9700	N2—P2	1.575 (2)
C8—H8B	0.9700	N2—P3	1.601 (2)
C9—O6	1.428 (4)	N3—P1	1.574 (2)
C9—C10	1.437 (5)	N3—P3	1.6027 (19)
C9—H9A	0.9700	O1—P1	1.5845 (18)
C9—H9B	0.9700	O2—P2	1.5745 (19)
C10—O7	1.454 (4)	O7—P2	1.5852 (19)
C10—H10A	0.9700	O3—P1	1.5733 (18)

O1—C1—H1A	109.5	C12—C11—P3	118.7 (2)
O1—C1—H1B	109.5	C13—C12—C11	120.6 (3)
H1A—C1—H1B	109.5	C13—C12—H12	119.7
O1—C1—H1C	109.5	C11—C12—H12	119.7
H1A—C1—H1C	109.5	C14—C13—C12	120.4 (4)
H1B—C1—H1C	109.5	C14—C13—H13	119.8
O2—C2—H2A	109.5	C12—C13—H13	119.8
O2—C2—H2B	109.5	C13—C14—C15	119.5 (3)
H2A—C2—H2B	109.5	C13—C14—H14	120.2
O2—C2—H2C	109.5	C15—C14—H14	120.2
H2A—C2—H2C	109.5	C14—C15—C16	121.1 (3)
H2B—C2—H2C	109.5	C14—C15—H15	119.4
O3—C3—C4	109.1 (3)	C16—C15—H15	119.4
O3—C3—H3A	109.9	C11—C16—C15	119.3 (3)
C4—C3—H3A	109.9	C11—C16—H16	120.4
O3—C3—H3B	109.9	C15—C16—H16	120.4
C4—C3—H3B	109.9	C22—C17—C18	119.1 (2)
H3A—C3—H3B	108.3	C22—C17—P3	120.1 (2)
O4—C4—C3	108.6 (3)	C18—C17—P3	120.7 (2)
O4—C4—H4A	110.0	C19—C18—C17	120.3 (3)
C3—C4—H4A	110.0	C19—C18—H18	119.9
O4—C4—H4B	110.0	C17—C18—H18	119.9
C3—C4—H4B	110.0	C20—C19—C18	120.3 (3)
H4A—C4—H4B	108.3	C20—C19—H19	119.8
O4—C5—C6	109.3 (4)	C18—C19—H19	119.8
O4—C5—H5A	109.8	C21—C20—C19	120.6 (3)
C6—C5—H5A	109.8	C21—C20—H20	119.7
O4—C5—H5B	109.8	C19—C20—H20	119.7
C6—C5—H5B	109.8	C20—C21—C22	119.9 (3)
H5A—C5—H5B	108.3	C20—C21—H21	120.0
O5—C6—C5	109.9 (4)	C22—C21—H21	120.0
O5—C6—H6A	109.7	C17—C22—C21	119.8 (3)
C5—C6—H6A	109.7	C17—C22—H22	120.1
O5—C6—H6B	109.7	C21—C22—H22	120.1
C5—C6—H6B	109.7	P1—N1—P2	122.96 (13)
H6A—C6—H6B	108.2	P2—N2—P3	121.30 (13)
O5—C7—C8	109.1 (4)	P1—N3—P3	120.91 (12)
O5—C7—H7A	109.9	C1—O1—P1	118.82 (17)
C8—C7—H7A	109.9	C2—O2—P2	121.6 (2)
O5—C7—H7B	109.9	C4—O4—C5	112.9 (4)
C8—C7—H7B	109.9	C6—O5—C7	111.5 (4)
H7A—C7—H7B	108.3	C9—O6—C8	114.1 (3)
O6—C8—C7	115.5 (4)	C10—O7—P2	117.11 (19)
O6—C8—H8A	108.4	C3—O3—P1	119.92 (18)
C7—C8—H8A	108.4	O3—P1—N3	106.50 (10)
O6—C8—H8B	108.4	O3—P1—N1	112.39 (11)
C7—C8—H8B	108.4	N3—P1—N1	117.06 (11)
H8A—C8—H8B	107.5	O3—P1—O1	99.50 (10)
O6—C9—C10	110.4 (3)	N3—P1—O1	111.66 (11)
O6—C9—H9A	109.6	N1—P1—O1	108.35 (11)
C10—C9—H9A	109.6	N2—P2—O2	111.65 (12)
O6—C9—H9B	109.6	N2—P2—O7	107.88 (11)
C10—C9—H9B	109.6	O2—P2—O7	98.83 (11)
H9A—C9—H9B	108.1	N2—P2—N1	116.77 (11)
C9—C10—O7	112.9 (3)	O2—P2—N1	109.07 (11)
C9—C10—H10A	109.0	O7—P2—N1	111.18 (12)
O7—C10—H10A	109.0	N3—P3—N2	117.33 (11)
C9—C10—H10B	109.0	N3—P3—C17	107.74 (11)
O7—C10—H10B	109.0	N2—P3—C17	109.39 (12)
H10A—C10—H10B	107.8	N3—P3—C11	107.10 (11)
C16—C11—C12	119.0 (3)	N2—P3—C11	109.37 (12)
C16—C11—P3	122.1 (2)	C17—P3—C11	105.23 (11)

O3—C3—C4—O4	72.9 (4)	P2—N1—P1—N3	−11.2 (2)
O4—C5—C6—O5	60.2 (5)	P2—N1—P1—O1	−138.55 (16)
O5—C7—C8—O6	−73.1 (5)	C1—O1—P1—O3	177.3 (2)
O6—C9—C10—O7	71.9 (4)	C1—O1—P1—N3	−70.6 (2)
C16—C11—C12—C13	−0.9 (5)	C1—O1—P1—N1	59.7 (2)
P3—C11—C12—C13	174.6 (3)	P3—N2—P2—O2	−128.62 (15)
C11—C12—C13—C14	−0.1 (6)	P3—N2—P2—O7	123.82 (16)
C12—C13—C14—C15	0.5 (6)	P3—N2—P2—N1	−2.2 (2)
C13—C14—C15—C16	0.1 (6)	C2—O2—P2—N2	82.1 (3)
C12—C11—C16—C15	1.5 (4)	C2—O2—P2—O7	−164.5 (3)
P3—C11—C16—C15	−173.9 (2)	C2—O2—P2—N1	−48.4 (3)
C14—C15—C16—C11	−1.1 (5)	C10—O7—P2—N2	176.2 (2)
C22—C17—C18—C19	−0.2 (4)	C10—O7—P2—O2	59.9 (2)
P3—C17—C18—C19	178.0 (2)	C10—O7—P2—N1	−54.6 (2)
C17—C18—C19—C20	−0.2 (5)	P1—N1—P2—N2	15.5 (2)
C18—C19—C20—C21	0.2 (5)	P1—N1—P2—O2	143.24 (17)
C19—C20—C21—C22	0.4 (5)	P1—N1—P2—O7	−108.81 (17)
C18—C17—C22—C21	0.7 (4)	P1—N3—P3—N2	18.8 (2)
P3—C17—C22—C21	−177.5 (2)	P1—N3—P3—C17	142.71 (15)
C20—C21—C22—C17	−0.8 (5)	P1—N3—P3—C11	−104.52 (16)
C3—C4—O4—C5	165.7 (3)	P2—N2—P3—N3	−14.3 (2)
C6—C5—O4—C4	178.0 (4)	P2—N2—P3—C17	−137.33 (15)
C5—C6—O5—C7	−165.9 (4)	P2—N2—P3—C11	107.91 (16)
C8—C7—O5—C6	164.0 (4)	C22—C17—P3—N3	−161.0 (2)
C10—C9—O6—C8	163.1 (4)	C18—C17—P3—N3	20.8 (2)
C7—C8—O6—C9	77.5 (6)	C22—C17—P3—N2	−32.4 (2)
C9—C10—O7—P2	131.0 (3)	C18—C17—P3—N2	149.4 (2)
C4—C3—O3—P1	−164.9 (2)	C22—C17—P3—C11	85.0 (2)
C3—O3—P1—N3	179.6 (2)	C18—C17—P3—C11	−93.2 (2)
C3—O3—P1—N1	50.2 (2)	C16—C11—P3—N3	127.7 (2)
C3—O3—P1—O1	−64.3 (2)	C12—C11—P3—N3	−47.7 (3)
P3—N3—P1—O3	−133.20 (14)	C16—C11—P3—N2	−0.4 (3)
P3—N3—P1—N1	−6.5 (2)	C12—C11—P3—N2	−175.8 (2)
P3—N3—P1—O1	119.16 (15)	C16—C11—P3—C17	−117.8 (2)
P2—N1—P1—O3	112.50 (17)	C12—C11—P3—C17	66.8 (2)

(7) top

Crystal data top

C₃₂H₄₀N₅O₆P₃	Z = 2
M_r = 683.60	F(000) = 720
Triclinic, P1	D_x = 1.368 Mg m⁻³
a = 10.519 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.694 (3) Å	Cell parameters from 11413 reflections
c = 14.340 (3) Å	θ = 2.9–27.5°
α = 114.81 (3)°	µ = 0.23 mm⁻¹
β = 93.81 (3)°	T = 150 K
γ = 103.59 (3)°	Block, colourless
V = 1659.6 (6) Å³	0.30 × 0.17 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	7460 independent reflections
Radiation source: Nonius FR591 rotating anode	6157 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan SORTAV (Blessing, 1997)	k = −16→15
T_min = 0.934, T_max = 0.983	l = −17→18
19478 measured reflections

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 0.65	w = 1/[σ²(F_o²) + (0.0981P)² + 3.4222P] where P = (F_o² + 2F_c²)/3
7460 reflections	(Δ/σ)_max = 0.005
431 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₃₂H₄₀N₅O₆P₃	γ = 103.59 (3)°
M_r = 683.60	V = 1659.6 (6) Å³
Triclinic, P1	Z = 2
a = 10.519 (2) Å	Mo Kα radiation
b = 12.694 (3) Å	µ = 0.23 mm⁻¹
c = 14.340 (3) Å	T = 150 K
α = 114.81 (3)°	0.30 × 0.17 × 0.08 mm
β = 93.81 (3)°

Data collection top

Nonius KappaCCD diffractometer	7460 independent reflections
Absorption correction: multi-scan SORTAV (Blessing, 1997)	6157 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.983	R_int = 0.033
19478 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 0.65	Δρ_max = 0.28 e Å⁻³
7460 reflections	Δρ_min = −0.45 e Å⁻³
431 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O6	1.17466 (14)	0.98464 (12)	0.45589 (10)	0.0252 (3)
C21	0.82058 (17)	0.76389 (16)	−0.00272 (14)	0.0222 (4)
C22	0.93610 (19)	0.84509 (17)	−0.00216 (15)	0.0268 (4)
H22	0.9659	0.9253	0.0530	0.032*
C23	1.0078 (2)	0.80890 (19)	−0.08215 (16)	0.0309 (4)
H23	1.0865	0.8645	−0.0814	0.037*
C24	0.9651 (2)	0.69219 (19)	−0.16285 (15)	0.0303 (4)
H24	1.0142	0.6681	−0.2175	0.036*
C25	0.8506 (2)	0.61029 (19)	−0.16403 (16)	0.0316 (4)
H25	0.8219	0.5299	−0.2190	0.038*
C26	0.77830 (19)	0.64609 (18)	−0.08474 (15)	0.0280 (4)
H26	0.6994	0.5902	−0.0861	0.034*
C27	0.56009 (17)	0.75962 (16)	0.04244 (13)	0.0224 (4)
C28	0.5147 (2)	0.83055 (19)	0.00353 (16)	0.0314 (4)
H28	0.5737	0.9037	0.0103	0.038*
C29	0.3830 (2)	0.7939 (2)	−0.04516 (18)	0.0385 (5)
H29	0.3513	0.8429	−0.0706	0.046*
C30	0.2974 (2)	0.6863 (2)	−0.05689 (16)	0.0365 (5)
H30	0.2073	0.6615	−0.0907	0.044*
C31	0.34218 (19)	0.61461 (19)	−0.01972 (15)	0.0323 (4)
H31	0.2835	0.5403	−0.0287	0.039*
C32	0.47359 (18)	0.65191 (17)	0.03082 (14)	0.0259 (4)
H32	0.5044	0.6035	0.0575	0.031*
C1	0.66710 (17)	0.68628 (16)	0.36827 (14)	0.0211 (3)
C2	0.62464 (19)	0.57036 (17)	0.28489 (15)	0.0261 (4)
H2	0.6680	0.5510	0.2264	0.031*
C3	0.5186 (2)	0.48309 (17)	0.28750 (16)	0.0291 (4)
H3	0.4895	0.4043	0.2302	0.035*
C4	0.4553 (2)	0.50945 (18)	0.37217 (17)	0.0320 (4)
H4	0.3823	0.4494	0.3729	0.038*
C5	0.4988 (2)	0.62423 (19)	0.45628 (16)	0.0309 (4)
H5	0.4565	0.6426	0.5153	0.037*
C6	0.60394 (18)	0.71218 (17)	0.45419 (14)	0.0242 (4)
H6	0.6331	0.7907	0.5118	0.029*
C7	0.82853 (17)	1.21778 (16)	0.40024 (14)	0.0225 (4)
C8	0.8577 (2)	1.30967 (18)	0.50242 (15)	0.0291 (4)
H8	0.8878	1.2953	0.5588	0.035*
C9	0.8428 (2)	1.42195 (19)	0.52146 (16)	0.0340 (4)
H9	0.8626	1.4844	0.5913	0.041*
C10	0.7993 (2)	1.44475 (19)	0.44009 (17)	0.0327 (4)
H10	0.7904	1.5224	0.4537	0.039*
C11	0.7691 (2)	1.35280 (19)	0.33912 (17)	0.0316 (4)
H11	0.7383	1.3672	0.2830	0.038*
C12	0.7831 (2)	1.23971 (18)	0.31873 (15)	0.0277 (4)
H12	0.7617	1.1771	0.2489	0.033*
C13	1.00165 (19)	0.65465 (18)	0.17645 (15)	0.0296 (4)
H13A	0.9557	0.6610	0.1174	0.036*
H13B	0.9959	0.5682	0.1538	0.036*
C14	1.14448 (19)	0.7267 (2)	0.20252 (15)	0.0301 (4)
H14A	1.1838	0.7031	0.1386	0.036*
H14B	1.1519	0.8141	0.2312	0.036*
C15	1.35466 (19)	0.73185 (19)	0.28393 (17)	0.0309 (4)
H15A	1.3752	0.7247	0.2155	0.037*
H15B	1.3858	0.6711	0.2977	0.037*
C16	1.4309 (2)	0.85736 (18)	0.36814 (17)	0.0321 (4)
H16A	1.4133	0.8633	0.4369	0.038*
H16B	1.5274	0.8680	0.3693	0.038*
C17	1.4360 (2)	0.9653 (2)	0.26494 (17)	0.0325 (4)
H17A	1.3832	0.8937	0.2004	0.039*
H17B	1.5314	0.9703	0.2653	0.039*
C18	1.41154 (19)	1.07805 (19)	0.26819 (17)	0.0318 (4)
H18A	1.4695	1.1502	0.3300	0.038*
H18B	1.4319	1.0859	0.2046	0.038*
C19	1.24327 (19)	1.17620 (17)	0.28454 (16)	0.0280 (4)
H19A	1.2284	1.1755	0.2153	0.034*
H19B	1.3174	1.2490	0.3309	0.034*
C20	1.11903 (18)	1.17974 (16)	0.33047 (15)	0.0249 (4)
H20A	1.1272	1.1632	0.3919	0.030*
H20B	1.1060	1.2611	0.3538	0.030*
N1	0.93565 (14)	0.91753 (13)	0.31140 (12)	0.0209 (3)
N2	0.77713 (15)	0.94920 (13)	0.17428 (12)	0.0221 (3)
N3	0.74437 (15)	0.72396 (13)	0.16301 (11)	0.0212 (3)
N4	0.77009 (15)	0.77953 (14)	0.36814 (12)	0.0219 (3)
N5	0.84618 (16)	1.10404 (14)	0.38169 (12)	0.0241 (3)
O1	0.93503 (12)	0.69567 (11)	0.26425 (10)	0.0235 (3)
O2	1.21402 (13)	0.70438 (14)	0.27757 (11)	0.0319 (3)
O3	1.39789 (14)	0.95393 (13)	0.35467 (11)	0.0295 (3)
O4	1.27593 (13)	1.07003 (12)	0.27390 (12)	0.0307 (3)
O5	1.00655 (12)	1.08896 (11)	0.25160 (10)	0.0231 (3)
P1	0.84447 (4)	0.78142 (4)	0.27162 (3)	0.01863 (11)
P2	0.88797 (4)	1.00921 (4)	0.27737 (3)	0.01905 (11)
P3	0.73149 (4)	0.80545 (4)	0.10466 (3)	0.01933 (11)
H4N	0.787 (3)	0.845 (2)	0.418 (2)	0.037 (7)*
H5N	0.843 (2)	1.086 (2)	0.429 (2)	0.034 (6)*
H01	1.095 (3)	0.964 (3)	0.412 (3)	0.063 (9)*
H02	1.234 (3)	0.975 (2)	0.421 (2)	0.039 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O6	0.0253 (7)	0.0287 (7)	0.0187 (6)	0.0080 (5)	0.0035 (5)	0.0079 (5)
C21	0.0230 (8)	0.0264 (9)	0.0189 (8)	0.0091 (7)	0.0024 (7)	0.0109 (7)
C22	0.0270 (9)	0.0270 (9)	0.0261 (9)	0.0073 (7)	0.0059 (7)	0.0118 (8)
C23	0.0255 (9)	0.0384 (11)	0.0337 (10)	0.0093 (8)	0.0088 (8)	0.0203 (9)
C24	0.0316 (10)	0.0420 (11)	0.0241 (9)	0.0183 (9)	0.0102 (8)	0.0164 (9)
C25	0.0357 (11)	0.0321 (10)	0.0244 (9)	0.0134 (8)	0.0057 (8)	0.0083 (8)
C26	0.0275 (9)	0.0280 (9)	0.0238 (9)	0.0063 (8)	0.0046 (7)	0.0081 (8)
C27	0.0217 (8)	0.0254 (9)	0.0153 (8)	0.0083 (7)	0.0026 (6)	0.0041 (7)
C28	0.0321 (10)	0.0319 (10)	0.0275 (10)	0.0086 (8)	−0.0017 (8)	0.0122 (8)
C29	0.0365 (11)	0.0453 (12)	0.0344 (11)	0.0170 (10)	−0.0031 (9)	0.0171 (10)
C30	0.0236 (10)	0.0481 (13)	0.0263 (10)	0.0099 (9)	−0.0022 (8)	0.0074 (9)
C31	0.0236 (9)	0.0362 (11)	0.0258 (10)	0.0039 (8)	0.0030 (7)	0.0063 (8)
C32	0.0249 (9)	0.0270 (9)	0.0223 (9)	0.0078 (7)	0.0046 (7)	0.0076 (7)
C1	0.0190 (8)	0.0234 (8)	0.0223 (8)	0.0047 (7)	0.0006 (6)	0.0128 (7)
C2	0.0293 (9)	0.0228 (9)	0.0263 (9)	0.0092 (7)	0.0047 (7)	0.0101 (7)
C3	0.0310 (10)	0.0198 (9)	0.0331 (10)	0.0048 (7)	−0.0006 (8)	0.0110 (8)
C4	0.0275 (10)	0.0288 (10)	0.0395 (11)	−0.0004 (8)	0.0009 (8)	0.0204 (9)
C5	0.0285 (10)	0.0340 (10)	0.0300 (10)	0.0035 (8)	0.0052 (8)	0.0171 (8)
C6	0.0239 (9)	0.0251 (9)	0.0213 (8)	0.0032 (7)	0.0020 (7)	0.0107 (7)
C7	0.0224 (8)	0.0229 (8)	0.0223 (9)	0.0079 (7)	0.0068 (7)	0.0093 (7)
C8	0.0359 (10)	0.0293 (10)	0.0209 (9)	0.0116 (8)	0.0057 (8)	0.0091 (8)
C9	0.0426 (12)	0.0274 (10)	0.0263 (10)	0.0128 (9)	0.0091 (9)	0.0051 (8)
C10	0.0377 (11)	0.0274 (10)	0.0385 (11)	0.0164 (8)	0.0145 (9)	0.0151 (9)
C11	0.0375 (11)	0.0353 (11)	0.0325 (10)	0.0191 (9)	0.0119 (8)	0.0196 (9)
C12	0.0338 (10)	0.0306 (10)	0.0214 (9)	0.0151 (8)	0.0064 (7)	0.0110 (8)
C13	0.0276 (9)	0.0300 (10)	0.0248 (9)	0.0133 (8)	0.0037 (7)	0.0039 (8)
C14	0.0290 (10)	0.0401 (11)	0.0241 (9)	0.0141 (8)	0.0069 (8)	0.0147 (8)
C15	0.0249 (9)	0.0326 (10)	0.0364 (11)	0.0130 (8)	0.0036 (8)	0.0144 (9)
C16	0.0300 (10)	0.0330 (10)	0.0342 (11)	0.0135 (8)	0.0015 (8)	0.0145 (9)
C17	0.0297 (10)	0.0374 (11)	0.0343 (11)	0.0133 (8)	0.0131 (8)	0.0167 (9)
C18	0.0253 (9)	0.0371 (11)	0.0364 (11)	0.0088 (8)	0.0099 (8)	0.0192 (9)
C19	0.0259 (9)	0.0267 (9)	0.0337 (10)	0.0047 (7)	0.0016 (8)	0.0179 (8)
C20	0.0234 (9)	0.0202 (8)	0.0241 (9)	0.0008 (7)	−0.0033 (7)	0.0074 (7)
N1	0.0197 (7)	0.0211 (7)	0.0206 (7)	0.0045 (6)	0.0007 (6)	0.0093 (6)
N2	0.0239 (7)	0.0214 (7)	0.0191 (7)	0.0067 (6)	0.0000 (6)	0.0078 (6)
N3	0.0232 (7)	0.0191 (7)	0.0170 (7)	0.0031 (6)	−0.0011 (6)	0.0065 (6)
N4	0.0230 (7)	0.0196 (7)	0.0184 (7)	0.0020 (6)	0.0034 (6)	0.0066 (6)
N5	0.0335 (9)	0.0241 (8)	0.0180 (7)	0.0108 (6)	0.0057 (6)	0.0112 (6)
O1	0.0235 (6)	0.0240 (6)	0.0253 (6)	0.0098 (5)	0.0054 (5)	0.0114 (5)
O2	0.0241 (7)	0.0437 (8)	0.0320 (7)	0.0111 (6)	0.0046 (6)	0.0201 (6)
O3	0.0322 (7)	0.0320 (7)	0.0291 (7)	0.0149 (6)	0.0096 (6)	0.0148 (6)
O4	0.0238 (7)	0.0275 (7)	0.0436 (8)	0.0070 (5)	0.0065 (6)	0.0186 (6)
O5	0.0227 (6)	0.0228 (6)	0.0210 (6)	0.0018 (5)	0.0006 (5)	0.0101 (5)
P1	0.0182 (2)	0.0196 (2)	0.0177 (2)	0.00543 (16)	0.00222 (16)	0.00827 (17)
P2	0.0200 (2)	0.0188 (2)	0.0170 (2)	0.00481 (17)	0.00134 (16)	0.00751 (17)
P3	0.0191 (2)	0.0203 (2)	0.0165 (2)	0.00533 (17)	0.00102 (16)	0.00692 (17)

Geometric parameters (Å, º) top

O6—H01	0.92 (3)	C10—C11	1.381 (3)
O6—H02	0.83 (3)	C10—H10	0.9500
C21—C22	1.394 (3)	C11—C12	1.386 (3)
C21—C26	1.400 (3)	C11—H11	0.9500
C21—P3	1.8083 (19)	C12—H12	0.9500
C22—C23	1.390 (3)	C13—O1	1.444 (2)
C22—H22	0.9500	C13—C14	1.492 (3)
C23—C24	1.384 (3)	C13—H13A	0.9900
C23—H23	0.9500	C13—H13B	0.9900
C24—C25	1.387 (3)	C14—O2	1.422 (2)
C24—H24	0.9500	C14—H14A	0.9900
C25—C26	1.386 (3)	C14—H14B	0.9900
C25—H25	0.9500	C15—O2	1.425 (2)
C26—H26	0.9500	C15—C16	1.515 (3)
C27—C28	1.392 (3)	C15—H15A	0.9900
C27—C32	1.389 (3)	C15—H15B	0.9900
C27—P3	1.8009 (19)	C16—O3	1.432 (2)
C28—C29	1.385 (3)	C16—H16A	0.9900
C28—H28	0.9500	C16—H16B	0.9900
C29—C30	1.384 (3)	C17—O3	1.426 (2)
C29—H29	0.9500	C17—C18	1.495 (3)
C30—C31	1.381 (3)	C17—H17A	0.9900
C30—H30	0.9500	C17—H17B	0.9900
C31—C32	1.390 (3)	C18—O4	1.416 (2)
C31—H31	0.9500	C18—H18A	0.9900
C32—H32	0.9500	C18—H18B	0.9900
C1—C6	1.392 (3)	C19—O4	1.418 (2)
C1—C2	1.392 (3)	C19—C20	1.504 (3)
C1—N4	1.405 (2)	C19—H19A	0.9900
C2—C3	1.390 (3)	C19—H19B	0.9900
C2—H2	0.9500	C20—O5	1.447 (2)
C3—C4	1.379 (3)	C20—H20A	0.9900
C3—H3	0.9500	C20—H20B	0.9900
C4—C5	1.388 (3)	N1—P1	1.5974 (16)
C4—H4	0.9500	N1—P2	1.6007 (15)
C5—C6	1.386 (3)	N2—P2	1.5918 (17)
C5—H5	0.9500	N2—P3	1.5978 (17)
C6—H6	0.9500	N3—P1	1.5920 (16)
C7—C12	1.390 (3)	N3—P3	1.6017 (15)
C7—C8	1.393 (3)	N4—P1	1.6404 (16)
C7—N5	1.414 (2)	N4—H4N	0.80 (3)
C8—C9	1.384 (3)	N5—P2	1.6448 (17)
C8—H8	0.9500	N5—H5N	0.80 (3)
C9—C10	1.389 (3)	O1—P1	1.5836 (13)
C9—H9	0.9500	O5—P2	1.5808 (14)

H01—O6—H02	109 (3)	C14—C13—H13B	109.2
C22—C21—C26	119.06 (17)	H13A—C13—H13B	107.9
C22—C21—P3	121.00 (14)	O2—C14—C13	109.02 (17)
C26—C21—P3	119.82 (14)	O2—C14—H14A	109.9
C21—C22—C23	120.13 (18)	C13—C14—H14A	109.9
C21—C22—H22	119.9	O2—C14—H14B	109.9
C23—C22—H22	119.9	C13—C14—H14B	109.9
C24—C23—C22	120.32 (19)	H14A—C14—H14B	108.3
C24—C23—H23	119.8	O2—C15—C16	113.79 (17)
C22—C23—H23	119.8	O2—C15—H15A	108.8
C25—C24—C23	120.11 (18)	C16—C15—H15A	108.8
C25—C24—H24	119.9	O2—C15—H15B	108.8
C23—C24—H24	119.9	C16—C15—H15B	108.8
C26—C25—C24	119.81 (19)	H15A—C15—H15B	107.7
C26—C25—H25	120.1	O3—C16—C15	114.11 (16)
C24—C25—H25	120.1	O3—C16—H16A	108.7
C25—C26—C21	120.56 (19)	C15—C16—H16A	108.7
C25—C26—H26	119.7	O3—C16—H16B	108.7
C21—C26—H26	119.7	C15—C16—H16B	108.7
C28—C27—C32	119.78 (17)	H16A—C16—H16B	107.6
C28—C27—P3	120.10 (15)	O3—C17—C18	108.13 (16)
C32—C27—P3	120.10 (14)	O3—C17—H17A	110.1
C27—C28—C29	119.7 (2)	C18—C17—H17A	110.1
C27—C28—H28	120.2	O3—C17—H17B	110.1
C29—C28—H28	120.2	C18—C17—H17B	110.1
C30—C29—C28	120.3 (2)	H17A—C17—H17B	108.4
C30—C29—H29	119.9	O4—C18—C17	108.10 (16)
C28—C29—H29	119.9	O4—C18—H18A	110.1
C29—C30—C31	120.36 (19)	C17—C18—H18A	110.1
C29—C30—H30	119.8	O4—C18—H18B	110.1
C31—C30—H30	119.8	C17—C18—H18B	110.1
C30—C31—C32	119.6 (2)	H18A—C18—H18B	108.4
C30—C31—H31	120.2	O4—C19—C20	108.62 (15)
C32—C31—H31	120.2	O4—C19—H19A	110.0
C31—C32—C27	120.25 (19)	C20—C19—H19A	110.0
C31—C32—H32	119.9	O4—C19—H19B	110.0
C27—C32—H32	119.9	C20—C19—H19B	110.0
C6—C1—C2	119.21 (17)	H19A—C19—H19B	108.3
C6—C1—N4	118.46 (16)	O5—C20—C19	108.81 (15)
C2—C1—N4	122.32 (17)	O5—C20—H20A	109.9
C3—C2—C1	119.79 (18)	C19—C20—H20A	109.9
C3—C2—H2	120.1	O5—C20—H20B	109.9
C1—C2—H2	120.1	C19—C20—H20B	109.9
C4—C3—C2	120.85 (18)	H20A—C20—H20B	108.3
C4—C3—H3	119.6	P1—N1—P2	121.03 (9)
C2—C3—H3	119.6	P2—N2—P3	119.80 (10)
C3—C4—C5	119.55 (18)	P1—N3—P3	119.90 (9)
C3—C4—H4	120.2	C1—N4—P1	128.73 (13)
C5—C4—H4	120.2	C1—N4—H4N	117.0 (19)
C6—C5—C4	120.06 (19)	P1—N4—H4N	113.4 (19)
C6—C5—H5	120.0	C7—N5—P2	127.16 (13)
C4—C5—H5	120.0	C7—N5—H5N	117.4 (18)
C5—C6—C1	120.52 (18)	P2—N5—H5N	115.1 (18)
C5—C6—H6	119.7	C13—O1—P1	120.18 (12)
C1—C6—H6	119.7	C14—O2—C15	115.21 (16)
C12—C7—C8	119.46 (17)	C17—O3—C16	114.01 (15)
C12—C7—N5	121.41 (17)	C18—O4—C19	113.03 (15)
C8—C7—N5	119.13 (17)	C20—O5—P2	122.78 (12)
C9—C8—C7	119.69 (19)	O1—P1—N3	108.57 (8)
C9—C8—H8	120.2	O1—P1—N1	109.90 (8)
C7—C8—H8	120.2	N3—P1—N1	116.23 (9)
C8—C9—C10	121.02 (19)	O1—P1—N4	101.60 (8)
C8—C9—H9	119.5	N3—P1—N4	113.24 (8)
C10—C9—H9	119.5	N1—P1—N4	106.30 (9)
C11—C10—C9	118.97 (19)	O5—P2—N2	103.21 (8)
C11—C10—H10	120.5	O5—P2—N1	111.49 (8)
C9—C10—H10	120.5	N2—P2—N1	116.27 (8)
C10—C11—C12	120.73 (19)	O5—P2—N5	105.94 (8)
C10—C11—H11	119.6	N2—P2—N5	114.05 (9)
C12—C11—H11	119.6	N1—P2—N5	105.54 (8)
C7—C12—C11	120.12 (18)	N2—P3—N3	117.25 (8)
C7—C12—H12	119.9	N2—P3—C27	108.31 (9)
C11—C12—H12	119.9	N3—P3—C27	107.84 (9)
O1—C13—C14	112.15 (16)	N2—P3—C21	110.36 (9)
O1—C13—H13A	109.2	N3—P3—C21	107.95 (8)
C14—C13—H13A	109.2	C27—P3—C21	104.34 (8)
O1—C13—H13B	109.2

C26—C21—C22—C23	0.0 (3)	C17—C18—O4—C19	175.98 (16)
P3—C21—C22—C23	175.91 (15)	C20—C19—O4—C18	−158.44 (16)
C21—C22—C23—C24	0.0 (3)	C19—C20—O5—P2	141.23 (13)
C22—C23—C24—C25	−0.4 (3)	C13—O1—P1—N3	49.60 (15)
C23—C24—C25—C26	0.7 (3)	C13—O1—P1—N1	−78.53 (15)
C24—C25—C26—C21	−0.7 (3)	C13—O1—P1—N4	169.20 (13)
C22—C21—C26—C25	0.4 (3)	P3—N3—P1—O1	−129.09 (10)
P3—C21—C26—C25	−175.60 (15)	P3—N3—P1—N1	−4.63 (14)
C32—C27—C28—C29	0.9 (3)	P3—N3—P1—N4	118.88 (11)
P3—C27—C28—C29	179.34 (16)	P2—N1—P1—O1	150.68 (10)
C27—C28—C29—C30	−1.2 (3)	P2—N1—P1—N3	26.91 (14)
C28—C29—C30—C31	0.3 (3)	P2—N1—P1—N4	−100.13 (12)
C29—C30—C31—C32	0.8 (3)	C1—N4—P1—O1	−74.15 (17)
C30—C31—C32—C27	−1.1 (3)	C1—N4—P1—N3	42.08 (18)
C28—C27—C32—C31	0.2 (3)	C1—N4—P1—N1	170.89 (15)
P3—C27—C32—C31	−178.23 (14)	C20—O5—P2—N2	166.92 (13)
C6—C1—C2—C3	1.3 (3)	C20—O5—P2—N1	−67.56 (15)
N4—C1—C2—C3	−177.38 (17)	C20—O5—P2—N5	46.76 (15)
C1—C2—C3—C4	−0.5 (3)	P3—N2—P2—O5	115.82 (11)
C2—C3—C4—C5	−0.7 (3)	P3—N2—P2—N1	−6.55 (14)
C3—C4—C5—C6	1.0 (3)	P3—N2—P2—N5	−129.74 (11)
C4—C5—C6—C1	−0.3 (3)	P1—N1—P2—O5	−139.24 (10)
C2—C1—C6—C5	−0.9 (3)	P1—N1—P2—N2	−21.33 (14)
N4—C1—C6—C5	177.81 (17)	P1—N1—P2—N5	106.19 (12)
C12—C7—C8—C9	−0.8 (3)	C7—N5—P2—O5	45.16 (18)
N5—C7—C8—C9	179.04 (18)	C7—N5—P2—N2	−67.65 (18)
C7—C8—C9—C10	−0.1 (3)	C7—N5—P2—N1	163.51 (15)
C8—C9—C10—C11	0.9 (3)	P2—N2—P3—N3	27.64 (14)
C9—C10—C11—C12	−0.7 (3)	P2—N2—P3—C27	149.87 (11)
C8—C7—C12—C11	1.0 (3)	P2—N2—P3—C21	−96.48 (12)
N5—C7—C12—C11	−178.83 (18)	P1—N3—P3—N2	−21.75 (14)
C10—C11—C12—C7	−0.3 (3)	P1—N3—P3—C27	−144.23 (10)
O1—C13—C14—O2	66.6 (2)	P1—N3—P3—C21	103.58 (12)
O2—C15—C16—O3	−60.6 (2)	C28—C27—P3—N2	39.48 (17)
O3—C17—C18—O4	−56.3 (2)	C32—C27—P3—N2	−142.09 (15)
O4—C19—C20—O5	−72.65 (19)	C28—C27—P3—N3	167.30 (15)
C6—C1—N4—P1	−169.29 (14)	C32—C27—P3—N3	−14.27 (17)
C2—C1—N4—P1	9.3 (3)	C28—C27—P3—C21	−78.09 (17)
C12—C7—N5—P2	31.2 (3)	C32—C27—P3—C21	100.33 (16)
C8—C7—N5—P2	−148.62 (16)	C22—C21—P3—N2	16.56 (17)
C14—C13—O1—P1	99.94 (17)	C26—C21—P3—N2	−167.52 (14)
C13—C14—O2—C15	159.52 (16)	C22—C21—P3—N3	−112.76 (15)
C16—C15—O2—C14	94.9 (2)	C26—C21—P3—N3	63.16 (16)
C18—C17—O3—C16	−172.93 (16)	C22—C21—P3—C27	132.72 (15)
C15—C16—O3—C17	−66.6 (2)	C26—C21—P3—C27	−51.37 (17)

(8) top

Crystal data top

C₂₈H₄₆N₅O₅P₃	Z = 2
M_r = 625.61	F(000) = 668
Triclinic, P1	D_x = 1.296 Mg m⁻³
a = 9.5003 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4210 (3) Å	Cell parameters from 12052 reflections
c = 17.1257 (3) Å	θ = 2.9–27.5°
α = 92.598 (2)°	µ = 0.23 mm⁻¹
β = 90.645 (2)°	T = 120 K
γ = 108.799 (1)°	Block, colourless
V = 1602.79 (6) Å³	0.27 × 0.18 × 0.12 mm

Data collection top

Nonius KappaCCD diffractometer	7079 independent reflections
Radiation source: Nonius FR591 rotating anode	5682 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −12→12
Absorption correction: multi-scan SORTAV (Blessing, 1997)	k = −13→13
T_min = 0.941, T_max = 0.973	l = −22→19
20859 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0461P)² + 1.1656P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.029
7079 reflections	Δρ_max = 0.72 e Å⁻³
385 parameters	Δρ_min = −0.48 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (15)

Crystal data top

C₂₈H₄₆N₅O₅P₃	γ = 108.799 (1)°
M_r = 625.61	V = 1602.79 (6) Å³
Triclinic, P1	Z = 2
a = 9.5003 (2) Å	Mo Kα radiation
b = 10.4210 (3) Å	µ = 0.23 mm⁻¹
c = 17.1257 (3) Å	T = 120 K
α = 92.598 (2)°	0.27 × 0.18 × 0.12 mm
β = 90.645 (2)°

Data collection top

Nonius KappaCCD diffractometer	7079 independent reflections
Absorption correction: multi-scan SORTAV (Blessing, 1997)	5682 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.973	R_int = 0.091
20859 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.72 e Å⁻³
7079 reflections	Δρ_min = −0.48 e Å⁻³
385 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.3736 (2)	0.0629 (2)	0.31806 (12)	0.0232 (4)
C2	0.2276 (2)	−0.0502 (3)	0.29802 (14)	0.0344 (5)
H2A	0.1939	−0.0405	0.2450	0.052*
H2B	0.1522	−0.0442	0.3353	0.052*
H2C	0.2430	−0.1385	0.3009	0.052*
C3	0.3488 (3)	0.2004 (2)	0.31825 (15)	0.0366 (6)
H3A	0.4430	0.2726	0.3309	0.055*
H3B	0.2756	0.2038	0.3575	0.055*
H3C	0.3118	0.2132	0.2665	0.055*
C4	0.4321 (2)	0.0396 (3)	0.39724 (13)	0.0318 (5)
H4A	0.4464	−0.0495	0.3957	0.048*
H4B	0.3604	0.0429	0.4373	0.048*
H4C	0.5273	0.1104	0.4098	0.048*
C5	0.7337 (2)	0.6212 (2)	0.21172 (12)	0.0227 (4)
C6	0.7158 (3)	0.5919 (3)	0.12430 (14)	0.0407 (6)
H6A	0.7871	0.5473	0.1067	0.061*
H6B	0.7344	0.6772	0.0981	0.061*
H6C	0.6144	0.5322	0.1114	0.061*
C7	0.8906 (2)	0.7206 (2)	0.23173 (14)	0.0320 (5)
H7A	0.9040	0.7357	0.2886	0.048*
H7B	0.9025	0.8072	0.2080	0.048*
H7C	0.9652	0.6821	0.2113	0.048*
C8	0.6204 (3)	0.6860 (2)	0.24175 (15)	0.0350 (5)
H8A	0.5198	0.6218	0.2328	0.053*
H8B	0.6304	0.7684	0.2139	0.053*
H8C	0.6383	0.7093	0.2979	0.053*
C9	0.8606 (2)	0.0568 (2)	0.33826 (12)	0.0232 (4)
H9A	0.9239	0.1262	0.3047	0.028*
H9B	0.8937	−0.0241	0.3341	0.028*
C10	0.8766 (2)	0.1117 (2)	0.42160 (12)	0.0266 (5)
H10A	0.8363	0.1881	0.4271	0.032*
H10B	0.8214	0.0400	0.4563	0.032*
C11	1.0599 (2)	0.2223 (3)	0.51739 (13)	0.0320 (5)
H11A	1.0244	0.1551	0.5578	0.038*
H11B	1.0072	0.2900	0.5231	0.038*
C12	1.2252 (3)	0.2916 (3)	0.52765 (13)	0.0347 (5)
H12A	1.2488	0.3227	0.5832	0.042*
H12B	1.2771	0.2253	0.5145	0.042*
C13	1.2788 (3)	0.5310 (3)	0.51706 (16)	0.0480 (7)
H13A	1.3458	0.5527	0.5640	0.058*
H13B	1.1772	0.5229	0.5340	0.058*
C14	1.3291 (3)	0.6407 (3)	0.46211 (16)	0.0452 (7)
H14A	1.3570	0.7290	0.4923	0.054*
H14B	1.4197	0.6340	0.4366	0.054*
C15	1.2135 (2)	0.5511 (2)	0.33720 (14)	0.0320 (5)
H15A	1.2966	0.5136	0.3406	0.038*
H15B	1.2255	0.6029	0.2893	0.038*
C16	1.0702 (2)	0.4370 (2)	0.33087 (14)	0.0288 (5)
H16A	1.0746	0.3718	0.2879	0.035*
H16B	1.0539	0.3887	0.3801	0.035*
C17	0.9988 (2)	0.1785 (2)	0.11671 (11)	0.0194 (4)
C18	0.9824 (2)	0.0417 (2)	0.10682 (12)	0.0241 (4)
H18	0.8875	−0.0243	0.1121	0.029*
C19	1.1042 (3)	0.0007 (2)	0.08927 (13)	0.0327 (5)
H19	1.0927	−0.0932	0.0828	0.039*
C20	1.2408 (3)	0.0956 (3)	0.08131 (14)	0.0360 (6)
H20	1.3235	0.0670	0.0687	0.043*
C21	1.2598 (3)	0.2317 (3)	0.09129 (16)	0.0394 (6)
H21	1.3552	0.2967	0.0854	0.047*
C22	1.1392 (2)	0.2742 (2)	0.11003 (14)	0.0304 (5)
H22	1.1524	0.3682	0.1183	0.037*
C23	0.7737 (2)	0.24617 (19)	0.03569 (11)	0.0181 (4)
C24	0.6302 (2)	0.1739 (2)	0.00908 (13)	0.0255 (4)
H24	0.5634	0.1151	0.0428	0.031*
C25	0.5835 (2)	0.1867 (2)	−0.06616 (14)	0.0327 (5)
H25	0.4852	0.1364	−0.0839	0.039*
C26	0.6799 (2)	0.2727 (2)	−0.11554 (13)	0.0296 (5)
H26	0.6481	0.2812	−0.1673	0.036*
C27	0.8233 (2)	0.3466 (2)	−0.08931 (12)	0.0253 (4)
H27	0.8892	0.4067	−0.1228	0.030*
C28	0.8699 (2)	0.3326 (2)	−0.01459 (12)	0.0211 (4)
H28	0.9685	0.3824	0.0028	0.025*
N1	0.72087 (17)	0.26791 (16)	0.30129 (9)	0.0182 (3)
N2	0.88823 (17)	0.37503 (16)	0.17868 (9)	0.0192 (3)
N3	0.71138 (17)	0.10801 (16)	0.17107 (9)	0.0197 (3)
N4	0.47903 (18)	0.05308 (17)	0.25655 (10)	0.0199 (4)
N5	0.7113 (2)	0.49711 (17)	0.25515 (10)	0.0235 (4)
O1	0.70748 (14)	0.02057 (13)	0.31231 (8)	0.0206 (3)
O2	1.03044 (15)	0.15663 (16)	0.44202 (8)	0.0274 (3)
O3	1.27911 (18)	0.40478 (17)	0.48005 (9)	0.0348 (4)
O4	1.22158 (19)	0.63974 (18)	0.40256 (11)	0.0438 (5)
O5	0.94914 (15)	0.48741 (14)	0.31600 (8)	0.0235 (3)
P1	0.65997 (5)	0.12130 (5)	0.25830 (3)	0.01615 (13)
P2	0.81718 (5)	0.39971 (5)	0.25967 (3)	0.01652 (13)
P3	0.83675 (5)	0.22942 (5)	0.13334 (3)	0.01621 (13)
H5	0.610 (3)	0.450 (3)	0.2648 (18)	0.058 (9)*
H4	0.445 (3)	0.040 (3)	0.2153 (17)	0.041 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0163 (9)	0.0275 (11)	0.0223 (11)	0.0021 (8)	0.0048 (7)	0.0020 (8)
C2	0.0179 (10)	0.0420 (14)	0.0341 (13)	−0.0033 (9)	0.0041 (9)	0.0027 (10)
C3	0.0352 (13)	0.0341 (13)	0.0432 (14)	0.0138 (10)	0.0161 (10)	0.0048 (10)
C4	0.0260 (11)	0.0437 (14)	0.0212 (11)	0.0045 (10)	0.0053 (8)	0.0043 (9)
C5	0.0256 (10)	0.0176 (10)	0.0260 (11)	0.0080 (8)	0.0012 (8)	0.0053 (8)
C6	0.0624 (17)	0.0337 (13)	0.0294 (13)	0.0204 (12)	−0.0063 (11)	0.0026 (10)
C7	0.0298 (12)	0.0240 (11)	0.0397 (14)	0.0048 (9)	0.0031 (9)	0.0056 (9)
C8	0.0383 (13)	0.0304 (12)	0.0432 (14)	0.0200 (10)	0.0003 (10)	0.0051 (10)
C9	0.0184 (9)	0.0251 (11)	0.0271 (11)	0.0084 (8)	−0.0013 (8)	0.0013 (8)
C10	0.0198 (10)	0.0317 (12)	0.0270 (11)	0.0059 (9)	0.0016 (8)	0.0053 (9)
C11	0.0297 (12)	0.0435 (14)	0.0215 (11)	0.0096 (10)	−0.0007 (8)	0.0044 (9)
C12	0.0314 (12)	0.0474 (15)	0.0234 (12)	0.0100 (11)	−0.0047 (9)	0.0055 (10)
C13	0.0538 (17)	0.0498 (17)	0.0346 (15)	0.0113 (13)	0.0009 (12)	−0.0188 (12)
C14	0.0422 (15)	0.0382 (15)	0.0479 (16)	0.0060 (12)	−0.0174 (12)	−0.0152 (12)
C15	0.0212 (10)	0.0359 (13)	0.0359 (13)	0.0052 (9)	0.0005 (9)	0.0002 (10)
C16	0.0281 (11)	0.0237 (11)	0.0349 (13)	0.0093 (9)	−0.0062 (9)	−0.0021 (9)
C17	0.0197 (9)	0.0219 (10)	0.0181 (10)	0.0086 (8)	0.0027 (7)	0.0031 (7)
C18	0.0283 (11)	0.0249 (11)	0.0222 (11)	0.0129 (9)	0.0010 (8)	0.0019 (8)
C19	0.0446 (14)	0.0362 (13)	0.0272 (12)	0.0269 (11)	0.0021 (9)	0.0007 (9)
C20	0.0322 (12)	0.0541 (16)	0.0330 (13)	0.0291 (12)	0.0080 (9)	0.0053 (11)
C21	0.0202 (11)	0.0484 (16)	0.0515 (16)	0.0127 (10)	0.0087 (10)	0.0101 (12)
C22	0.0215 (10)	0.0284 (12)	0.0425 (14)	0.0090 (9)	0.0061 (9)	0.0047 (9)
C23	0.0182 (9)	0.0166 (9)	0.0201 (10)	0.0067 (7)	0.0018 (7)	−0.0021 (7)
C24	0.0192 (10)	0.0249 (11)	0.0302 (12)	0.0037 (8)	0.0012 (8)	0.0050 (8)
C25	0.0237 (11)	0.0349 (13)	0.0366 (13)	0.0053 (9)	−0.0081 (9)	0.0043 (10)
C26	0.0344 (12)	0.0328 (12)	0.0242 (12)	0.0140 (10)	−0.0033 (9)	0.0052 (9)
C27	0.0307 (11)	0.0217 (10)	0.0262 (11)	0.0111 (9)	0.0079 (8)	0.0054 (8)
C28	0.0199 (9)	0.0185 (10)	0.0237 (11)	0.0045 (8)	0.0032 (7)	−0.0004 (7)
N1	0.0183 (8)	0.0159 (8)	0.0175 (8)	0.0020 (6)	0.0015 (6)	−0.0018 (6)
N2	0.0182 (8)	0.0143 (8)	0.0221 (9)	0.0016 (6)	0.0016 (6)	−0.0014 (6)
N3	0.0202 (8)	0.0144 (8)	0.0204 (9)	0.0002 (6)	0.0041 (6)	−0.0024 (6)
N4	0.0142 (8)	0.0239 (9)	0.0175 (9)	0.0006 (6)	0.0009 (6)	−0.0006 (7)
N5	0.0231 (9)	0.0193 (9)	0.0284 (10)	0.0070 (7)	0.0020 (7)	0.0042 (7)
O1	0.0179 (7)	0.0175 (7)	0.0251 (8)	0.0037 (5)	−0.0012 (5)	0.0027 (5)
O2	0.0201 (7)	0.0367 (9)	0.0238 (8)	0.0069 (6)	−0.0017 (6)	0.0016 (6)
O3	0.0359 (9)	0.0374 (9)	0.0268 (9)	0.0066 (7)	0.0007 (6)	−0.0039 (7)
O4	0.0370 (10)	0.0403 (10)	0.0521 (12)	0.0130 (8)	−0.0162 (8)	−0.0181 (8)
O5	0.0204 (7)	0.0220 (7)	0.0246 (8)	0.0025 (6)	−0.0044 (5)	−0.0034 (6)
P1	0.0138 (2)	0.0141 (2)	0.0182 (3)	0.00145 (18)	0.00126 (17)	−0.00036 (17)
P2	0.0167 (2)	0.0133 (2)	0.0184 (3)	0.00338 (18)	−0.00132 (17)	−0.00102 (17)
P3	0.0140 (2)	0.0139 (2)	0.0194 (3)	0.00269 (18)	0.00293 (17)	−0.00023 (18)

Geometric parameters (Å, º) top

C1—N4	1.484 (2)	C14—H14A	0.9900
C1—C4	1.519 (3)	C14—H14B	0.9900
C1—C3	1.526 (3)	C15—O4	1.404 (3)
C1—C2	1.526 (3)	C15—C16	1.490 (3)
C2—H2A	0.9800	C15—H15A	0.9900
C2—H2B	0.9800	C15—H15B	0.9900
C2—H2C	0.9800	C16—O5	1.435 (3)
C3—H3A	0.9800	C16—H16A	0.9900
C3—H3B	0.9800	C16—H16B	0.9900
C3—H3C	0.9800	C17—C18	1.386 (3)
C4—H4A	0.9800	C17—C22	1.394 (3)
C4—H4B	0.9800	C17—P3	1.8044 (19)
C4—H4C	0.9800	C18—C19	1.388 (3)
C5—N5	1.478 (3)	C18—H18	0.9500
C5—C6	1.511 (3)	C19—C20	1.367 (3)
C5—C8	1.525 (3)	C19—H19	0.9500
C5—C7	1.541 (3)	C20—C21	1.374 (4)
C6—H6A	0.9800	C20—H20	0.9500
C6—H6B	0.9800	C21—C22	1.391 (3)
C6—H6C	0.9800	C21—H21	0.9500
C7—H7A	0.9800	C22—H22	0.9500
C7—H7B	0.9800	C23—C24	1.388 (3)
C7—H7C	0.9800	C23—C28	1.395 (3)
C8—H8A	0.9800	C23—P3	1.805 (2)
C8—H8B	0.9800	C24—C25	1.384 (3)
C8—H8C	0.9800	C24—H24	0.9500
C9—O1	1.440 (2)	C25—C26	1.384 (3)
C9—C10	1.501 (3)	C25—H25	0.9500
C9—H9A	0.9900	C26—C27	1.389 (3)
C9—H9B	0.9900	C26—H26	0.9500
C10—O2	1.418 (2)	C27—C28	1.378 (3)
C10—H10A	0.9900	C27—H27	0.9500
C10—H10B	0.9900	C28—H28	0.9500
C11—O2	1.415 (3)	N1—P2	1.5891 (16)
C11—C12	1.506 (3)	N1—P1	1.5905 (16)
C11—H11A	0.9900	N2—P2	1.5957 (16)
C11—H11B	0.9900	N2—P3	1.5972 (16)
C12—O3	1.423 (3)	N3—P1	1.5908 (16)
C12—H12A	0.9900	N3—P3	1.5992 (16)
C12—H12B	0.9900	N4—P1	1.6341 (16)
C13—O3	1.434 (3)	N4—H4	0.76 (3)
C13—C14	1.476 (4)	N5—P2	1.6470 (18)
C13—H13A	0.9900	N5—H5	0.95 (3)
C13—H13B	0.9900	O1—P1	1.5954 (14)
C14—O4	1.433 (3)	O5—P2	1.5786 (14)

N4—C1—C4	109.83 (17)	C13—C14—H14B	108.6
N4—C1—C3	110.44 (17)	H14A—C14—H14B	107.6
C4—C1—C3	111.09 (19)	O4—C15—C16	112.71 (19)
N4—C1—C2	106.50 (17)	O4—C15—H15A	109.1
C4—C1—C2	109.04 (18)	C16—C15—H15A	109.1
C3—C1—C2	109.82 (19)	O4—C15—H15B	109.1
C1—C2—H2A	109.5	C16—C15—H15B	109.1
C1—C2—H2B	109.5	H15A—C15—H15B	107.8
H2A—C2—H2B	109.5	O5—C16—C15	110.32 (18)
C1—C2—H2C	109.5	O5—C16—H16A	109.6
H2A—C2—H2C	109.5	C15—C16—H16A	109.6
H2B—C2—H2C	109.5	O5—C16—H16B	109.6
C1—C3—H3A	109.5	C15—C16—H16B	109.6
C1—C3—H3B	109.5	H16A—C16—H16B	108.1
H3A—C3—H3B	109.5	C18—C17—C22	119.29 (18)
C1—C3—H3C	109.5	C18—C17—P3	119.36 (15)
H3A—C3—H3C	109.5	C22—C17—P3	121.28 (16)
H3B—C3—H3C	109.5	C17—C18—C19	120.2 (2)
C1—C4—H4A	109.5	C17—C18—H18	119.9
C1—C4—H4B	109.5	C19—C18—H18	119.9
H4A—C4—H4B	109.5	C20—C19—C18	120.0 (2)
C1—C4—H4C	109.5	C20—C19—H19	120.0
H4A—C4—H4C	109.5	C18—C19—H19	120.0
H4B—C4—H4C	109.5	C19—C20—C21	120.8 (2)
N5—C5—C6	112.47 (18)	C19—C20—H20	119.6
N5—C5—C8	106.63 (17)	C21—C20—H20	119.6
C6—C5—C8	111.03 (19)	C20—C21—C22	119.9 (2)
N5—C5—C7	108.85 (17)	C20—C21—H21	120.1
C6—C5—C7	109.53 (19)	C22—C21—H21	120.1
C8—C5—C7	108.19 (18)	C21—C22—C17	119.8 (2)
C5—C6—H6A	109.5	C21—C22—H22	120.1
C5—C6—H6B	109.5	C17—C22—H22	120.1
H6A—C6—H6B	109.5	C24—C23—C28	118.82 (18)
C5—C6—H6C	109.5	C24—C23—P3	121.18 (15)
H6A—C6—H6C	109.5	C28—C23—P3	119.99 (14)
H6B—C6—H6C	109.5	C25—C24—C23	120.68 (19)
C5—C7—H7A	109.5	C25—C24—H24	119.7
C5—C7—H7B	109.5	C23—C24—H24	119.7
H7A—C7—H7B	109.5	C26—C25—C24	120.0 (2)
C5—C7—H7C	109.5	C26—C25—H25	120.0
H7A—C7—H7C	109.5	C24—C25—H25	120.0
H7B—C7—H7C	109.5	C25—C26—C27	119.9 (2)
C5—C8—H8A	109.5	C25—C26—H26	120.1
C5—C8—H8B	109.5	C27—C26—H26	120.1
H8A—C8—H8B	109.5	C28—C27—C26	119.94 (19)
C5—C8—H8C	109.5	C28—C27—H27	120.0
H8A—C8—H8C	109.5	C26—C27—H27	120.0
H8B—C8—H8C	109.5	C27—C28—C23	120.69 (18)
O1—C9—C10	109.58 (16)	C27—C28—H28	119.7
O1—C9—H9A	109.8	C23—C28—H28	119.7
C10—C9—H9A	109.8	P2—N1—P1	123.56 (10)
O1—C9—H9B	109.8	P2—N2—P3	121.21 (10)
C10—C9—H9B	109.8	P1—N3—P3	121.55 (10)
H9A—C9—H9B	108.2	C1—N4—P1	128.16 (14)
O2—C10—C9	107.31 (16)	C1—N4—H4	114 (2)
O2—C10—H10A	110.3	P1—N4—H4	113 (2)
C9—C10—H10A	110.3	C5—N5—P2	129.13 (14)
O2—C10—H10B	110.3	C5—N5—H5	113.7 (19)
C9—C10—H10B	110.3	P2—N5—H5	112.8 (19)
H10A—C10—H10B	108.5	C9—O1—P1	118.53 (12)
O2—C11—C12	108.55 (18)	C11—O2—C10	112.13 (16)
O2—C11—H11A	110.0	C12—O3—C13	113.91 (19)
C12—C11—H11A	110.0	C15—O4—C14	115.60 (19)
O2—C11—H11B	110.0	C16—O5—P2	118.41 (13)
C12—C11—H11B	110.0	N1—P1—N3	116.52 (8)
H11A—C11—H11B	108.4	N1—P1—O1	106.65 (8)
O3—C12—C11	112.73 (18)	N3—P1—O1	110.61 (8)
O3—C12—H12A	109.0	N1—P1—N4	114.64 (9)
C11—C12—H12A	109.0	N3—P1—N4	106.50 (9)
O3—C12—H12B	109.0	O1—P1—N4	100.81 (8)
C11—C12—H12B	109.0	O5—P2—N1	110.05 (8)
H12A—C12—H12B	107.8	O5—P2—N2	107.11 (8)
O3—C13—C14	110.0 (2)	N1—P2—N2	116.41 (8)
O3—C13—H13A	109.7	O5—P2—N5	102.25 (8)
C14—C13—H13A	109.7	N1—P2—N5	105.62 (9)
O3—C13—H13B	109.7	N2—P2—N5	114.48 (9)
C14—C13—H13B	109.7	N2—P3—N3	118.32 (8)
H13A—C13—H13B	108.2	N2—P3—C17	108.54 (9)
O4—C14—C13	114.8 (2)	N3—P3—C17	108.97 (9)
O4—C14—H14A	108.6	N2—P3—C23	108.99 (9)
C13—C14—H14A	108.6	N3—P3—C23	107.84 (9)
O4—C14—H14B	108.6	C17—P3—C23	103.12 (9)

O1—C9—C10—O2	−174.98 (15)	P3—N3—P1—O1	−112.92 (12)
O2—C11—C12—O3	69.5 (3)	P3—N3—P1—N4	138.40 (12)
O3—C13—C14—O4	75.1 (3)	C9—O1—P1—N1	−50.98 (15)
O4—C15—C16—O5	66.0 (3)	C9—O1—P1—N3	76.63 (15)
C22—C17—C18—C19	−1.0 (3)	C9—O1—P1—N4	−170.99 (14)
P3—C17—C18—C19	176.09 (16)	C1—N4—P1—N1	−36.3 (2)
C17—C18—C19—C20	−0.3 (3)	C1—N4—P1—N3	−166.73 (17)
C18—C19—C20—C21	0.7 (4)	C1—N4—P1—O1	77.79 (18)
C19—C20—C21—C22	0.3 (4)	C16—O5—P2—N1	71.35 (16)
C20—C21—C22—C17	−1.6 (4)	C16—O5—P2—N2	−56.07 (16)
C18—C17—C22—C21	1.9 (3)	C16—O5—P2—N5	−176.77 (15)
P3—C17—C22—C21	−175.09 (18)	P1—N1—P2—O5	−137.73 (11)
C28—C23—C24—C25	0.4 (3)	P1—N1—P2—N2	−15.66 (16)
P3—C23—C24—C25	−179.43 (17)	P1—N1—P2—N5	112.60 (12)
C23—C24—C25—C26	−0.3 (3)	P3—N2—P2—O5	136.41 (11)
C24—C25—C26—C27	−0.3 (3)	P3—N2—P2—N1	12.81 (15)
C25—C26—C27—C28	0.9 (3)	P3—N2—P2—N5	−111.01 (12)
C26—C27—C28—C23	−0.9 (3)	C5—N5—P2—O5	75.56 (19)
C24—C23—C28—C27	0.2 (3)	C5—N5—P2—N1	−169.28 (17)
P3—C23—C28—C27	−179.95 (15)	C5—N5—P2—N2	−39.9 (2)
C4—C1—N4—P1	−45.8 (2)	P2—N2—P3—N3	0.08 (16)
C3—C1—N4—P1	77.1 (2)	P2—N2—P3—C17	−124.68 (12)
C2—C1—N4—P1	−163.68 (16)	P2—N2—P3—C23	123.68 (12)
C6—C5—N5—P2	69.8 (2)	P1—N3—P3—N2	−11.53 (16)
C8—C5—N5—P2	−168.29 (16)	P1—N3—P3—C17	113.02 (12)
C7—C5—N5—P2	−51.8 (2)	P1—N3—P3—C23	−135.71 (12)
C10—C9—O1—P1	101.89 (17)	C18—C17—P3—N2	155.28 (16)
C12—C11—O2—C10	−168.37 (18)	C22—C17—P3—N2	−27.7 (2)
C9—C10—O2—C11	174.44 (18)	C18—C17—P3—N3	25.15 (19)
C11—C12—O3—C13	90.4 (2)	C22—C17—P3—N3	−157.84 (17)
C14—C13—O3—C12	−177.1 (2)	C18—C17—P3—C23	−89.22 (17)
C16—C15—O4—C14	112.9 (2)	C22—C17—P3—C23	87.78 (18)
C13—C14—O4—C15	−82.5 (3)	C24—C23—P3—N2	−121.33 (17)
C15—C16—O5—P2	143.27 (16)	C28—C23—P3—N2	58.87 (17)
P2—N1—P1—N3	4.97 (16)	C24—C23—P3—N3	8.30 (19)
P2—N1—P1—O1	129.01 (11)	C28—C23—P3—N3	−171.50 (15)
P2—N1—P1—N4	−120.35 (12)	C24—C23—P3—C17	123.49 (17)
P3—N3—P1—N1	9.06 (16)	C28—C23—P3—C17	−56.31 (17)

Experimental details

	(3)	(4)	(5)	(6)
Crystal data
Chemical formula	C₂₀H₂₆Cl₂N₃O₅P₃	C₂₄H₃₀F₆N₃O₇P₃	C₃₂H₃₆N₃O₇P₃	C₂₂H₃₂N₃O₇P₃
M_r	552.25	679.42	667.55	543.42
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/n	Triclinic, P1	Monoclinic, P2₁/n
Temperature (K)	150	120	150	293
a, b, c (Å)	17.618 (4), 8.1109 (16), 19.284 (4)	15.3839 (4), 8.0685 (2), 24.1935 (9)	10.166 (2), 12.105 (2), 13.313 (3)	11.8293 (2), 10.3312 (2), 21.6318 (5)
α, β, γ (°)	90, 114.44 (3), 90	90, 105.877 (1), 90	88.86 (3), 86.54 (3), 78.14 (3)	90, 100.203 (1), 90
V (Å³)	2508.8 (9)	2888.46 (15)	1600.4 (6)	2601.84 (9)
Z	4	4	2	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.49	0.29	0.24	0.28
Crystal size (mm)	0.32 × 0.28 × 0.13	0.18 × 0.10 × 0.03	0.20 × 0.15 × 0.10	0.26 × 0.20 × 0.07

Data collection
Diffractometer	Nonius KappaCCD diffractometer	Nonius KappaCCD diffractometer	Bruker-Nonius KappaCCD diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan SORTAV (Blessing, 1997)	Multi-scan SORTAV (Blessing, 1997)	Multi-scan SORTAV (Blessing, 1997)	Multi-scan SORTAV (Blessing, 1997)
T_min, T_max	0.860, 0.939	0.949, 0.991	0.954, 0.977	0.932, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	17345, 5657, 4268	22797, 6488, 3777	24220, 12306, 8750	18814, 5841, 4160
R_int	0.045	0.083	0.061	0.038
(sin θ/λ)_max (Å⁻¹)	0.649	0.649	0.649	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.01	0.050, 0.114, 0.98	0.054, 0.132, 0.94	0.052, 0.153, 1.00
No. of reflections	5657	6488	12306	5841
No. of parameters	299	389	824	319
No. of restraints	0	0	22	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.46	0.38, −0.38	0.81, −0.40	0.46, −0.31
Absolute structure	?	?	Flack H D (1983), Acta Cryst. A39, 876-881	?
Absolute structure parameter	?	?	0.03 (7)	?

	(7)	(8)
Crystal data
Chemical formula	C₃₂H₄₀N₅O₆P₃	C₂₈H₄₆N₅O₅P₃
M_r	683.60	625.61
Crystal system, space group	Triclinic, P1	Triclinic, P1
Temperature (K)	150	120
a, b, c (Å)	10.519 (2), 12.694 (3), 14.340 (3)	9.5003 (2), 10.4210 (3), 17.1257 (3)
α, β, γ (°)	114.81 (3), 93.81 (3), 103.59 (3)	92.598 (2), 90.645 (2), 108.799 (1)
V (Å³)	1659.6 (6)	1602.79 (6)
Z	2	2
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.23	0.23
Crystal size (mm)	0.30 × 0.17 × 0.08	0.27 × 0.18 × 0.12

Data collection
Diffractometer	Nonius KappaCCD diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan SORTAV (Blessing, 1997)	Multi-scan SORTAV (Blessing, 1997)
T_min, T_max	0.934, 0.983	0.941, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	19478, 7460, 6157	20859, 7079, 5682
R_int	0.033	0.091
(sin θ/λ)_max (Å⁻¹)	0.649	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.120, 0.65	0.045, 0.125, 1.01
No. of reflections	7460	7079
No. of parameters	431	385
No. of restraints	0	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.45	0.72, −0.48
Absolute structure	?	?
Absolute structure parameter	?	?

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998), DENZO & COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1990).

Format		BIBTeX
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Format		BIBTeX
		EndNote
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		Refer
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		CIF
		SGML
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		Plain Text

Structural investigations of phosphorus–nitrogen compounds. 5. Relationships between molecular parameters of 2,2-diphenyl-4,6-cis-oxytetra­(ethyl­ene­oxy)-4,6-R2-cyclotriphosphazatrienes (R = Cl, OCH2CF3, OPh, OMe, NHPh, NHBut) and substituent basicity constants

Supporting information

Structural investigations of phosphorus–nitrogen compounds. 5. Relationships between molecular parameters of 2,2-diphenyl-4,6-cis-oxytetra(ethyleneoxy)-4,6-R₂-cyclotriphosphazatrienes (R = Cl, OCH₂CF₃, OPh, OMe, NHPh, NHBu^t) and substituent basicity constants