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In the title compound, C24H24N5O4P3, the mol­ecules are linked by rather weak N—H...N hydrogen bonds into chains propagating along the c axis, their planar P3N3 rings being approximately coplanar within the chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033399/dn3046sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033399/dn3046Isup2.hkl
Contains datablock I

CCDC reference: 657766

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.025
  • wR factor = 0.058
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N4 - H1 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N4 - H2 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N5 - H4 ... ?
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.99 From the CIF: _reflns_number_total 4919 Count of symmetry unique reflns 2572 Completeness (_total/calc) 191.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2347 Fraction of Friedel pairs measured 0.913 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Alkoxy- or aryloxy- substituted cyclo-triphosphazenes are generally suitable precursors for polymerization reactions in plasma. This present work is part of a study of plasma action on selected derivatives of cyclo-triphosphazenes. The plasma effect leads to the formation of polyorganophosphazenes, that are potentially attractive as fire retardants (Otsuka Chemical Company, 1985; Allcock & Taylor, 2000, Kanebo, 1991) and water repellents due to the presence of hydrophobic aryloxy- groups (Allcock, 2003).

Diamidotetrachloro-cyclo-triphosphazene, P3N3(Cl)4(NH2)2 (I) with a geminal structure (Fincham et al., 1986) is a common starting compound for syntheses of all known tetrasubstituted alkoxy-/aryloxy-2,2-diamino-1,3,5–2λ5,4λ 5,6λ 5-cyclo-triazatriphosphorines. In a majority of cases these substitution rections lead to a migration of the –NH2 group and a non-geminaly substituted P3N3(OR)4(NH2)2: (gem) P(NH2)2 (non-gem) P(NH2)(OR) results. Thus, non-geminaly substituted trans-P3N3(OR)4(NH2)2, (R = Me, Et, Prn, Bun) (Fincham et al., 1985,1986) and cis-P3N3(OR)4(NH2)2, (R = Me, Et, Prn, Bun) as a minor product (Fincham et al., 1985,1988) were obtained. However, the only X-ray structure known is that of trans-P3N3(OPrn)4(NH2)2 (II) (Fincham et al., 1985).

The only case when a substitution of Cl atoms by –OR group was not accompanied by a migration of a –NH2 group is gem-P3N3(OMe)4(NH2)2 (III)(Fincham et al., 1988). However, this derivative was not obtained as a chemical individuum and only the structure of 1:1 mixed crystals of cis-P3N3(OMe)4(NH2)2 (IV)and gem-P3N3(OMe)4(NH2)2 (III) have been determined.

In the title compound (V), the PN ring is fairly planar with N3 being 0.25 Å out of the best plane defined by P1, N1, P2, N2 and P3 (Fig. 1) and exhibits the same lengthening of the P—N ring bonds adjacent to P(NH2)2 and a shortening of the P—N ring bonds adjacent to P(OPh)2 as observed in other P3N3X4(NH2)2 derivatives. In this case Δ(P—N) is 0.03 Å which is equal to the value 0.03 Å found in gem-P3N3(OMe)4(NH2)2 (III)(Fincham et al., 1988).

The molecules are linked by rather weak N—H···N hydrogen bonds (Table 1) into chains propagating along the axis c with approximately coplanar orientation of their PN rings. This simple system of H-bonds is in a contrast to a very complicated H-bonds system in the structure of a 1:1 mixed crystal of (III) and (IV) which in fact prevents any mutual comparison. (Fincham et al., 1988).

There is a significant difference in the exocyclic P3—N4 1.646 (2) Å and P3—N5 1.628 (2) Å bond lengths, the shorter being that forming the hydrogen bond but the longer one 1.646 (2) Å equals to those found in P3N3(NH2)6 (av. 1.65 (2) Å) (Golinski & Jacobs,1994) and P3N3(NH2)6. 0.5NH3 (av.1.65 (1) Å) (Jacobs & Kirchgässner, 1990). On the other hand the P—O bond lengts (av. 1.594 (4) Å) are significantly longer than those found in P3N3(OPh)6 (av. 1.582 (2) Å) (Marsh & Trotter, 1971).

Related literature top

For general background, see: Otsuka Chemical Company (1985); Allcock & Taylor (2000); Kanebo (1991); Allcock (2003). For related structures, see: Fincham et al. (1985, 1988, 1986); Golinski & Jacobs (1994); Jacobs & Kirchgässner (1990); Marsh & Trotter (1971).

Experimental top

The reaction was carried out in anhydrous tetrahydrofuran (THF). 0.400 g (4.25 mmol) of PhOH was dissolved in 30 ml of THF. and 0.980 g (4.26 mmol) of Na was added to the solution, the reaction mixture was refluxed for 6 h and the PhONa was formed. 0.328 g (1.06 mmol) of (I) was added to the solution of PhONa. The reaction mixture was refluxed for 3.5 h and then was kept at ambient temperature for 5 days. After the reaction, the solvent was completely evaporated. 25 ml of Et2O was added to the solid (mixture of (V) and NaCl), (V) was dissolved and insoluble NaCl was filtered off. The solvent from the solution of (V) was then partially evaporated under vacuum. The yield of colourless crystals of (V) was 0.50 g (87%). The reaction and all operations were performed in an atmosphere of dry nitrogen.

Refinement top

Hydrogen atoms of phenyl rings were inserted in calculated position, those of –NH2 group were found from a difference electron density map. Non-hydrogen atoms were refined anisotropically, hydrogen atoms of the phenyl rings by a ride-on approach, and –NH2 group H atoms were refined isotropically with their isotropic temperature factors tied up with those of relevant nitrogen atoms.

Structure description top

Alkoxy- or aryloxy- substituted cyclo-triphosphazenes are generally suitable precursors for polymerization reactions in plasma. This present work is part of a study of plasma action on selected derivatives of cyclo-triphosphazenes. The plasma effect leads to the formation of polyorganophosphazenes, that are potentially attractive as fire retardants (Otsuka Chemical Company, 1985; Allcock & Taylor, 2000, Kanebo, 1991) and water repellents due to the presence of hydrophobic aryloxy- groups (Allcock, 2003).

Diamidotetrachloro-cyclo-triphosphazene, P3N3(Cl)4(NH2)2 (I) with a geminal structure (Fincham et al., 1986) is a common starting compound for syntheses of all known tetrasubstituted alkoxy-/aryloxy-2,2-diamino-1,3,5–2λ5,4λ 5,6λ 5-cyclo-triazatriphosphorines. In a majority of cases these substitution rections lead to a migration of the –NH2 group and a non-geminaly substituted P3N3(OR)4(NH2)2: (gem) P(NH2)2 (non-gem) P(NH2)(OR) results. Thus, non-geminaly substituted trans-P3N3(OR)4(NH2)2, (R = Me, Et, Prn, Bun) (Fincham et al., 1985,1986) and cis-P3N3(OR)4(NH2)2, (R = Me, Et, Prn, Bun) as a minor product (Fincham et al., 1985,1988) were obtained. However, the only X-ray structure known is that of trans-P3N3(OPrn)4(NH2)2 (II) (Fincham et al., 1985).

The only case when a substitution of Cl atoms by –OR group was not accompanied by a migration of a –NH2 group is gem-P3N3(OMe)4(NH2)2 (III)(Fincham et al., 1988). However, this derivative was not obtained as a chemical individuum and only the structure of 1:1 mixed crystals of cis-P3N3(OMe)4(NH2)2 (IV)and gem-P3N3(OMe)4(NH2)2 (III) have been determined.

In the title compound (V), the PN ring is fairly planar with N3 being 0.25 Å out of the best plane defined by P1, N1, P2, N2 and P3 (Fig. 1) and exhibits the same lengthening of the P—N ring bonds adjacent to P(NH2)2 and a shortening of the P—N ring bonds adjacent to P(OPh)2 as observed in other P3N3X4(NH2)2 derivatives. In this case Δ(P—N) is 0.03 Å which is equal to the value 0.03 Å found in gem-P3N3(OMe)4(NH2)2 (III)(Fincham et al., 1988).

The molecules are linked by rather weak N—H···N hydrogen bonds (Table 1) into chains propagating along the axis c with approximately coplanar orientation of their PN rings. This simple system of H-bonds is in a contrast to a very complicated H-bonds system in the structure of a 1:1 mixed crystal of (III) and (IV) which in fact prevents any mutual comparison. (Fincham et al., 1988).

There is a significant difference in the exocyclic P3—N4 1.646 (2) Å and P3—N5 1.628 (2) Å bond lengths, the shorter being that forming the hydrogen bond but the longer one 1.646 (2) Å equals to those found in P3N3(NH2)6 (av. 1.65 (2) Å) (Golinski & Jacobs,1994) and P3N3(NH2)6. 0.5NH3 (av.1.65 (1) Å) (Jacobs & Kirchgässner, 1990). On the other hand the P—O bond lengts (av. 1.594 (4) Å) are significantly longer than those found in P3N3(OPh)6 (av. 1.582 (2) Å) (Marsh & Trotter, 1971).

For general background, see: Otsuka Chemical Company (1985); Allcock & Taylor (2000); Kanebo (1991); Allcock (2003). For related structures, see: Fincham et al. (1985, 1988, 1986); Golinski & Jacobs (1994); Jacobs & Kirchgässner (1990); Marsh & Trotter (1971).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level. H atoms of the phenyl rings are omitted for clarity. Other H atoms are represented as small spheres of arbitrary radii.
gem-2,2-Diamino-4,4,6,6-tetraphenoxy-1,3,5–2λ5-cyclotriazaphosphorine top
Crystal data top
C24H24N5O4P3Dx = 1.420 Mg m3
Mr = 539.39Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41Cell parameters from 2718 reflections
a = 12.9555 (18) Åθ = 3.2–27.3°
c = 15.029 (3) ŵ = 0.28 mm1
V = 2522.5 (7) Å3T = 120 K
Z = 4Prism, colourless
F(000) = 11200.17 × 0.10 × 0.10 mm
Data collection top
Kuma KM-4 CCD area-detector
diffractometer
4919 independent reflections
Radiation source: fine-focus sealed tube4714 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 8.4353 pixels mm-1θmax = 26.0°, θmin = 3.4°
ω scansh = 1512
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2005)
k = 1515
Tmin = 0.924, Tmax = 0.973l = 1817
18062 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.058 w = 1/[σ2(Fo2) + (0.037P)2 + 0.2944P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4919 reflectionsΔρmax = 0.20 e Å3
337 parametersΔρmin = 0.29 e Å3
1 restraintAbsolute structure: Flack (1983), with 2339 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (4)
Crystal data top
C24H24N5O4P3Z = 4
Mr = 539.39Mo Kα radiation
Tetragonal, P41µ = 0.28 mm1
a = 12.9555 (18) ÅT = 120 K
c = 15.029 (3) Å0.17 × 0.10 × 0.10 mm
V = 2522.5 (7) Å3
Data collection top
Kuma KM-4 CCD area-detector
diffractometer
4919 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2005)
4714 reflections with I > 2σ(I)
Tmin = 0.924, Tmax = 0.973Rint = 0.045
18062 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.058Δρmax = 0.20 e Å3
S = 1.03Δρmin = 0.29 e Å3
4919 reflectionsAbsolute structure: Flack (1983), with 2339 Friedel pairs
337 parametersAbsolute structure parameter: 0.06 (4)
1 restraint
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
xyzUiso*/Ueq
P10.07004 (3)0.41977 (3)0.22059 (2)0.01416 (9)
N10.01277 (10)0.49632 (9)0.17903 (9)0.0179 (3)
P20.07227 (3)0.57612 (3)0.24143 (2)0.01442 (9)
N20.04300 (10)0.58137 (9)0.34272 (9)0.0187 (3)
P30.04153 (3)0.50759 (3)0.38884 (3)0.01613 (9)
N30.08060 (10)0.41581 (10)0.32482 (9)0.0183 (3)
N40.13070 (12)0.58672 (13)0.42667 (10)0.0266 (3)
H10.1451 (15)0.6358 (17)0.3909 (15)0.032*
H20.1868 (16)0.5602 (16)0.4479 (15)0.032*
N50.00452 (11)0.45057 (12)0.47995 (10)0.0234 (3)
H30.0038 (14)0.4852 (15)0.5267 (17)0.028*
H40.0324 (15)0.4041 (17)0.4779 (14)0.028*
O10.05456 (8)0.30671 (8)0.18133 (7)0.0192 (2)
C110.03274 (12)0.24610 (12)0.19850 (11)0.0178 (3)
C210.12032 (13)0.25927 (12)0.14673 (12)0.0243 (3)
H210.12360.31250.10340.029*
C310.20321 (14)0.19285 (14)0.15963 (12)0.0292 (4)
H310.26410.20120.12520.035*
C410.19795 (14)0.11462 (13)0.22217 (12)0.0301 (4)
H410.25450.06880.22980.036*
C510.10969 (15)0.10328 (14)0.27371 (13)0.0327 (4)
H510.10630.05010.31720.039*
C610.02613 (14)0.16957 (13)0.26189 (12)0.0261 (4)
H610.03440.16210.29700.031*
O20.17700 (8)0.44636 (8)0.17290 (7)0.0182 (2)
C120.26620 (12)0.38844 (12)0.19250 (10)0.0171 (3)
C220.29037 (12)0.30450 (12)0.13938 (11)0.0228 (3)
H220.24620.28440.09200.027*
C320.38075 (14)0.25036 (14)0.15707 (12)0.0285 (4)
H320.39860.19280.12110.034*
C420.44482 (13)0.27894 (14)0.22592 (13)0.0290 (4)
H420.50600.24080.23760.035*
C520.41943 (13)0.36446 (14)0.27865 (12)0.0274 (4)
H520.46350.38460.32610.033*
C620.32973 (13)0.41974 (13)0.26141 (11)0.0224 (3)
H620.31230.47820.29650.027*
O30.06784 (8)0.68823 (8)0.19750 (8)0.0194 (2)
C130.02350 (12)0.74692 (12)0.20296 (10)0.0179 (3)
C230.10722 (13)0.72322 (13)0.14915 (12)0.0243 (4)
H230.10550.66480.11100.029*
C330.19330 (13)0.78640 (14)0.15210 (13)0.0305 (4)
H330.25070.77210.11470.037*
C430.19631 (14)0.87029 (15)0.20919 (14)0.0342 (4)
H430.25590.91300.21130.041*
C530.11251 (15)0.89197 (15)0.26316 (13)0.0365 (5)
H530.11510.94890.30290.044*
C630.02444 (14)0.83060 (13)0.25939 (12)0.0286 (4)
H630.03400.84620.29510.034*
O40.19345 (8)0.55725 (8)0.23680 (7)0.0185 (2)
C140.25038 (11)0.53720 (12)0.15887 (10)0.0175 (3)
C240.25405 (13)0.60670 (13)0.08943 (11)0.0236 (4)
H240.21470.66860.09140.028*
C340.31641 (13)0.58452 (14)0.01644 (12)0.0270 (4)
H340.31970.63170.03190.032*
C440.37402 (13)0.49399 (13)0.01364 (11)0.0249 (4)
H440.41620.47920.03650.030*
C540.36950 (13)0.42588 (13)0.08406 (11)0.0234 (4)
H540.40880.36400.08230.028*
C640.30775 (12)0.44703 (12)0.15784 (11)0.0218 (3)
H640.30510.40040.20650.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01532 (18)0.01371 (18)0.0135 (2)0.00091 (13)0.00172 (15)0.00008 (14)
N10.0201 (7)0.0186 (7)0.0148 (6)0.0016 (5)0.0004 (5)0.0001 (5)
P20.01389 (18)0.01381 (18)0.0156 (2)0.00082 (14)0.00005 (14)0.00037 (15)
N20.0212 (7)0.0162 (7)0.0188 (7)0.0039 (5)0.0013 (5)0.0037 (5)
P30.01789 (19)0.01769 (19)0.01279 (18)0.00177 (15)0.00055 (15)0.00132 (15)
N30.0234 (7)0.0164 (6)0.0151 (7)0.0042 (5)0.0007 (5)0.0004 (5)
N40.0255 (8)0.0260 (8)0.0284 (8)0.0002 (6)0.0069 (6)0.0031 (6)
N50.0293 (8)0.0248 (7)0.0160 (7)0.0012 (6)0.0024 (6)0.0001 (6)
O10.0183 (6)0.0169 (5)0.0224 (6)0.0011 (4)0.0046 (4)0.0048 (4)
C110.0179 (8)0.0161 (8)0.0195 (8)0.0015 (6)0.0059 (6)0.0052 (6)
C210.0274 (9)0.0189 (8)0.0265 (9)0.0013 (6)0.0010 (7)0.0042 (7)
C310.0250 (9)0.0293 (9)0.0332 (10)0.0014 (7)0.0028 (7)0.0144 (8)
C410.0277 (9)0.0278 (9)0.0349 (10)0.0083 (7)0.0098 (8)0.0088 (8)
C510.0387 (11)0.0297 (9)0.0295 (10)0.0077 (8)0.0092 (8)0.0050 (8)
C610.0254 (9)0.0291 (9)0.0239 (9)0.0020 (7)0.0005 (7)0.0009 (7)
O20.0173 (5)0.0186 (5)0.0187 (6)0.0005 (4)0.0036 (4)0.0033 (4)
C120.0150 (7)0.0191 (8)0.0171 (8)0.0002 (6)0.0036 (6)0.0057 (6)
C220.0231 (8)0.0268 (8)0.0184 (8)0.0013 (7)0.0025 (7)0.0014 (7)
C320.0307 (9)0.0274 (9)0.0273 (9)0.0061 (7)0.0087 (7)0.0001 (7)
C420.0203 (8)0.0338 (9)0.0331 (9)0.0060 (7)0.0045 (7)0.0124 (8)
C520.0203 (8)0.0348 (10)0.0271 (9)0.0021 (7)0.0042 (7)0.0054 (7)
C620.0233 (8)0.0224 (8)0.0215 (8)0.0023 (7)0.0015 (6)0.0002 (6)
O30.0152 (5)0.0166 (5)0.0264 (6)0.0018 (4)0.0029 (4)0.0037 (4)
C130.0145 (7)0.0194 (8)0.0196 (8)0.0030 (6)0.0039 (6)0.0062 (6)
C230.0250 (8)0.0244 (8)0.0234 (9)0.0016 (7)0.0010 (7)0.0030 (7)
C330.0197 (8)0.0367 (10)0.0350 (10)0.0010 (7)0.0055 (7)0.0122 (8)
C430.0249 (9)0.0359 (10)0.0419 (11)0.0135 (8)0.0077 (8)0.0099 (8)
C530.0407 (11)0.0319 (10)0.0368 (11)0.0138 (8)0.0033 (9)0.0067 (8)
C630.0279 (9)0.0271 (9)0.0308 (10)0.0059 (7)0.0053 (7)0.0026 (7)
O40.0162 (5)0.0214 (5)0.0180 (5)0.0004 (4)0.0015 (4)0.0003 (5)
C140.0132 (7)0.0212 (8)0.0181 (8)0.0026 (6)0.0013 (6)0.0035 (6)
C240.0211 (8)0.0230 (8)0.0268 (9)0.0045 (7)0.0021 (7)0.0031 (7)
C340.0262 (9)0.0286 (9)0.0262 (9)0.0031 (7)0.0055 (7)0.0077 (7)
C440.0189 (8)0.0317 (9)0.0240 (8)0.0002 (7)0.0045 (6)0.0045 (7)
C540.0221 (8)0.0215 (8)0.0267 (9)0.0045 (7)0.0004 (7)0.0042 (7)
C640.0228 (8)0.0208 (8)0.0219 (8)0.0004 (6)0.0013 (7)0.0023 (6)
Geometric parameters (Å, º) top
P1—N31.5732 (14)C22—H220.9500
P1—N11.5889 (13)C32—C421.377 (3)
P1—O11.5918 (11)C32—H320.9500
P1—O21.5977 (11)C42—C521.401 (3)
N1—P21.5945 (13)C42—H420.9500
P2—N21.5704 (14)C52—C621.389 (2)
P2—O41.5904 (11)C52—H520.9500
P2—O31.5965 (11)C62—H620.9500
N2—P31.6104 (14)O3—C131.4089 (18)
P3—N31.6111 (13)C13—C631.376 (2)
P3—N51.6281 (15)C13—C231.387 (2)
P3—N41.6459 (16)C23—C331.384 (2)
N4—H10.85 (2)C23—H230.9500
N4—H20.86 (2)C33—C431.385 (3)
N5—H30.83 (2)C33—H330.9500
N5—H40.77 (2)C43—C531.384 (3)
O1—C111.4008 (18)C43—H430.9500
C11—C611.378 (2)C53—C631.392 (3)
C11—C211.386 (2)C53—H530.9500
C21—C311.390 (2)C63—H630.9500
C21—H210.9500O4—C141.4082 (18)
C31—C411.384 (3)C14—C241.379 (2)
C31—H310.9500C14—C641.385 (2)
C41—C511.389 (3)C24—C341.392 (2)
C41—H410.9500C24—H240.9500
C51—C611.393 (2)C34—C441.391 (2)
C51—H510.9500C34—H340.9500
C61—H610.9500C44—C541.379 (2)
O2—C121.4091 (19)C44—H440.9500
C12—C621.384 (2)C54—C641.394 (2)
C12—C221.385 (2)C54—H540.9500
C22—C321.391 (2)C64—H640.9500
N3—P1—N1118.06 (7)C32—C22—H22120.8
N3—P1—O1110.49 (6)C42—C32—C22121.03 (16)
N1—P1—O1110.09 (7)C42—C32—H32119.5
N3—P1—O2112.23 (7)C22—C32—H32119.5
N1—P1—O2105.94 (6)C32—C42—C52119.73 (16)
O1—P1—O298.13 (6)C32—C42—H42120.1
P1—N1—P2120.00 (9)C52—C42—H42120.1
N2—P2—O4106.70 (7)C62—C52—C42119.89 (16)
N2—P2—N1118.78 (7)C62—C52—H52120.1
O4—P2—N1110.60 (6)C42—C52—H52120.1
N2—P2—O3110.65 (7)C12—C62—C52119.08 (16)
O4—P2—O399.05 (6)C12—C62—H62120.5
N1—P2—O3109.23 (7)C52—C62—H62120.5
P2—N2—P3123.76 (8)C13—O3—P2119.81 (9)
N2—P3—N3113.25 (7)C63—C13—C23121.77 (15)
N2—P3—N5115.53 (7)C63—C13—O3117.93 (14)
N3—P3—N5105.07 (7)C23—C13—O3120.21 (14)
N2—P3—N4104.85 (8)C33—C23—C13118.71 (16)
N3—P3—N4116.45 (8)C33—C23—H23120.6
N5—P3—N4101.46 (9)C13—C23—H23120.6
P1—N3—P3122.90 (8)C23—C33—C43120.44 (17)
P3—N4—H1113.5 (14)C23—C33—H33119.8
P3—N4—H2118.0 (14)C43—C33—H33119.8
H1—N4—H2110 (2)C53—C43—C33120.01 (16)
P3—N5—H3117.9 (14)C53—C43—H43120.0
P3—N5—H4120.3 (16)C33—C43—H43120.0
H3—N5—H4117 (2)C43—C53—C63120.22 (17)
C11—O1—P1123.31 (9)C43—C53—H53119.9
C61—C11—C21121.84 (15)C63—C53—H53119.9
C61—C11—O1118.73 (14)C13—C63—C53118.83 (17)
C21—C11—O1119.23 (14)C13—C63—H63120.6
C11—C21—C31118.55 (16)C53—C63—H63120.6
C11—C21—H21120.7C14—O4—P2125.58 (10)
C31—C21—H21120.7C24—C14—C64121.58 (15)
C41—C31—C21120.68 (17)C24—C14—O4121.80 (14)
C41—C31—H31119.7C64—C14—O4116.50 (14)
C21—C31—H31119.7C14—C24—C34118.78 (15)
C31—C41—C51119.78 (16)C14—C24—H24120.6
C31—C41—H41120.1C34—C24—H24120.6
C51—C41—H41120.1C44—C34—C24120.61 (16)
C41—C51—C61120.23 (17)C44—C34—H34119.7
C41—C51—H51119.9C24—C34—H34119.7
C61—C51—H51119.9C54—C44—C34119.58 (15)
C11—C61—C51118.92 (16)C54—C44—H44120.2
C11—C61—H61120.5C34—C44—H44120.2
C51—C61—H61120.5C44—C54—C64120.58 (15)
C12—O2—P1120.17 (9)C44—C54—H54119.7
C62—C12—C22121.81 (15)C64—C54—H54119.7
C62—C12—O2119.23 (14)C14—C64—C54118.86 (15)
C22—C12—O2118.89 (14)C14—C64—H64120.6
C12—C22—C32118.44 (16)C54—C64—H64120.6
C12—C22—H22120.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H3···N1i0.83 (2)2.31 (3)3.072 (2)153.2 (18)
Symmetry code: (i) x, y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC24H24N5O4P3
Mr539.39
Crystal system, space groupTetragonal, P41
Temperature (K)120
a, c (Å)12.9555 (18), 15.029 (3)
V3)2522.5 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.17 × 0.10 × 0.10
Data collection
DiffractometerKuma KM-4 CCD area-detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2005)
Tmin, Tmax0.924, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
18062, 4919, 4714
Rint0.045
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.058, 1.03
No. of reflections4919
No. of parameters337
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.29
Absolute structureFlack (1983), with 2339 Friedel pairs
Absolute structure parameter0.06 (4)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H3···N1i0.83 (2)2.31 (3)3.072 (2)153.2 (18)
Symmetry code: (i) x, y+1, z+1/2.
 

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