2,4-Bis[bis(diisopropyl­amino)­phos­phanyl]-1,2,3,4-tetra­phospha­bicyclo[1.1.0]butane

Łapczuk-Krygier, A.; Baranowska*, K.; Pikies, J.

doi:10.1107/S1600536808037938

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2427

doi:10.1107/S1600536808037938

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2,4-Bis[bis(diisopropylamino)phosphanyl]-1,2,3,4-tetraphosphabicyclo[1.1.0]butane

Agnieszka Łapczuk-Krygier,^a Katarzyna Baranowska ^a ^* and Jerzy Pikies ^a

^aDepartment of Inorganic Chemistry, Faculty of Chemistry, Gdańsk University of Technology, 11/12 G. Narutowicz St., 80952 - PL Gdańsk, Poland
^*Correspondence e-mail: kasiab29@wp.pl

(Received 23 October 2008; accepted 14 November 2008; online 22 November 2008)

The title compound, C₂₄H₅₆N₄P₆ or (ⁱPr₂N)₂P–P₄–P(NⁱPr₂)₂, adopts a butterfly structure, with planar environments for the N atoms and pyramidal environments for the P atoms. The structure studied has a 15% twin component that is related by a twofold rotation about [100].

Related literature

For 2,4-bis{[bis(trimethylsilyl)amido](diisopropyloamido)phosphido}1,2,3,4-tetraphosphabicyclo(1,1,0)butane, see: Bezombes et al. (2004 ). For 2,4-bis(bis-di-tert-butylophosphido)1,2,3,4-tetraphosphabicyclo(1,1,0)butane, see: Matern et al. (1997 ). For the handling of twinned diffraction data, see: Spek (2003 ).

Experimental

Crystal data

C₂₄H₅₆N₄P₆
M_r = 586.55
Monoclinic, P 2₁ /c
a = 13.3307 (5) Å
b = 20.9304 (7) Å
c = 12.8939 (5) Å
β = 109.349 (4)°
V = 3394.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 120 (2) K
0.46 × 0.14 × 0.06 mm

Data collection

Oxford Diffraction KM-4 CCD diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.954, T_max = 1.045
6310 measured reflections
6310 independent reflections
4727 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.136
S = 1.04
6310 reflections
324 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037938/ng2506sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037938/ng2506Isup2.hkl

checkCIF report

Comment top

The molecular structure of 1 is shown in Fig.1. The crystal structure of 1 is build up of discrete molecules. The geometry of the phosphorous skeleton in 1 is similar to that in P₄[(NⁱPr₂)(N(SiMe₃)]₂ (Bezombes et al., 2004). The P1—P2 distance, 2.246 (2) Å, and P3—P4 distance, 2.243 (2) Å are slightly longer than P—P distances in the tetraphosphabicyclobutane core (P2,P5,P6,P4). The geometry around N atoms is strictly planar, the sum of angles around N2 atom is 360.8 °. The environments of P1 and P3 atoms are pyramidal, the sum of angles around P1 atom is 310.4 °. Clearly visible is very sharp pyramidal geometry around P2 and P4 atoms, the sum of angles around P2 atom is only 248.81 °.

Related literature top

For 2,4-bis{[bis(trimethylsilyl)amido](diisopropyloamido)phosphido}1,2,3,4-tetraphosphabicyclo(1,1,0)butane, see: Bezombes et al. (2004). For 2,4-bis(bis-di-tert-butylophosphido)1,2,3,4-tetraphosphabicyclo(1,1,0)butane, see: Matern et al. (1997). For the handling of twinned diffraction data, see: Spek (2003).

Experimental top

All operations were carried out under purified nitrogen using Schlenk techniques. (ⁱPr₂N)₂PP(SiMe₃)Li 2.5THF (0.170 g, 0.51 mmol) in toluene (5 ml) was dropped slowly to a suspension of Cp^*ZrCl₃(0.484 g, 0.94 mmol) in toluene (4 ml) at -30 °C.The reaction mixture turned immediately brown. The solution was allowed to stand one day at ambient temperature, then evaporated under reduced pressure and dried under vacuum (0.001 Torr) for 1 h. The residue was dissolved in 4 ml pentane and filtered. The solution was kept at 4 °C for two weeks and yielded small amount of colourless crystals of 1.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of the molecule of 1, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted.
	Fig. 2. Packing diagram for 1. View direction is parallel to the crystallographic b axis.

2,4-Bis[bis(diisopropylamino)phosphanyl]-1,2,3,4-tetraphosphabicyclo[1.1.0]butane top

Crystal data top

C₂₄H₅₆N₄P₆	F(000) = 1272
M_r = 586.55	D_x = 1.148 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10425 reflections
a = 13.3307 (5) Å	θ = 2.5–32.4°
b = 20.9304 (7) Å	µ = 0.34 mm⁻¹
c = 12.8939 (5) Å	T = 120 K
β = 109.349 (4)°	Prism, colourless
V = 3394.4 (2) Å³	0.46 × 0.14 × 0.06 mm
Z = 4

Data collection top

Oxford Diffraction KM-4 CCD diffractometer	6310 independent reflections
Graphite monochromator	4727 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm^-1	R_int = 0
ω scans, 0.75 deg width	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	h = −16→16
T_min = 0.955, T_max = 1.045	k = −25→25
6310 measured reflections	l = −13→15

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0841P)²] where P = (F_o² + 2F_c²)/3
6310 reflections	(Δ/σ)_max < 0.001
324 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₂₄H₅₆N₄P₆	V = 3394.4 (2) Å³
M_r = 586.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3307 (5) Å	µ = 0.34 mm⁻¹
b = 20.9304 (7) Å	T = 120 K
c = 12.8939 (5) Å	0.46 × 0.14 × 0.06 mm
β = 109.349 (4)°

Data collection top

Oxford Diffraction KM-4 CCD diffractometer	6310 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	4727 reflections with I > 2σ(I)
T_min = 0.955, T_max = 1.045	R_int = 0
6310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.04	Δρ_max = 0.61 e Å⁻³
6310 reflections	Δρ_min = −0.51 e Å⁻³
324 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	−0.1377 (2)	0.37879 (15)	0.4006 (3)	0.0268 (7)
H1	−0.0988	0.4188	0.4328	0.032*
C2	−0.2520 (3)	0.39804 (17)	0.3362 (3)	0.0348 (8)
H2A	−0.2524	0.426	0.2751	0.052*
H2B	−0.2829	0.4207	0.3849	0.052*
H2C	−0.2941	0.3597	0.3072	0.052*
C3	−0.1350 (3)	0.33570 (18)	0.4960 (3)	0.0361 (8)
H3A	−0.1759	0.2968	0.4679	0.054*
H3B	−0.166	0.3582	0.5448	0.054*
H3C	−0.0611	0.3243	0.5371	0.054*
C4	−0.1270 (3)	0.28996 (15)	0.2755 (3)	0.0284 (7)
H4	−0.1833	0.2767	0.3065	0.034*
C5	−0.1821 (3)	0.29992 (18)	0.1524 (3)	0.0400 (9)
H5A	−0.2318	0.3358	0.1407	0.06*
H5B	−0.2212	0.2611	0.1201	0.06*
H5C	−0.1288	0.3092	0.1174	0.06*
C6	−0.0471 (3)	0.23567 (17)	0.2981 (4)	0.0459 (10)
H6A	0.0082	0.2459	0.2662	0.069*
H6B	−0.0834	0.1962	0.2651	0.069*
H6C	−0.0146	0.2298	0.3777	0.069*
C7	−0.0671 (2)	0.49548 (15)	0.2373 (3)	0.0254 (7)
H7	−0.0924	0.4852	0.3002	0.03*
C8	−0.0059 (3)	0.55820 (16)	0.2653 (3)	0.0357 (8)
H8A	0.0566	0.5524	0.3312	0.053*
H8B	−0.0519	0.5913	0.2791	0.053*
H8C	0.017	0.5712	0.2037	0.053*
C9	−0.1655 (3)	0.50184 (17)	0.1357 (3)	0.0323 (8)
H9A	−0.1446	0.5165	0.0736	0.048*
H9B	−0.2144	0.5329	0.15	0.048*
H9C	−0.2009	0.4603	0.1181	0.048*
C10	0.0504 (2)	0.44695 (16)	0.1414 (3)	0.0266 (7)
H10	0.0203	0.4859	0.097	0.032*
C11	0.0259 (3)	0.39069 (18)	0.0623 (3)	0.0414 (9)
H11A	0.0546	0.3514	0.1027	0.062*
H11B	0.0586	0.3978	0.0054	0.062*
H11C	−0.0512	0.3865	0.0277	0.062*
C12	0.1705 (3)	0.4575 (2)	0.1920 (3)	0.0414 (9)
H12A	0.1842	0.4943	0.2418	0.062*
H12B	0.2006	0.4657	0.1335	0.062*
H12C	0.2037	0.4193	0.2331	0.062*
C13	0.5113 (2)	0.46488 (15)	0.8092 (3)	0.0252 (7)
H13	0.4396	0.4652	0.8182	0.03*
C14	0.5113 (3)	0.51854 (16)	0.7295 (3)	0.0355 (8)
H14A	0.5818	0.5217	0.7217	0.053*
H14B	0.4938	0.559	0.7578	0.053*
H14C	0.4582	0.5095	0.6577	0.053*
C15	0.5919 (3)	0.47724 (17)	0.9223 (3)	0.0334 (8)
H15A	0.5865	0.4436	0.973	0.05*
H15B	0.5775	0.5188	0.9494	0.05*
H15C	0.6637	0.4773	0.9173	0.05*
C16	0.6260 (3)	0.39185 (17)	0.7457 (3)	0.0373 (9)
H16	0.6652	0.4334	0.7631	0.045*
C17	0.6113 (4)	0.3773 (3)	0.6272 (5)	0.090 (2)
H17A	0.681	0.3745	0.6174	0.136*
H17B	0.5696	0.4114	0.5805	0.136*
H17C	0.5739	0.3365	0.6067	0.136*
C18	0.6957 (3)	0.3420 (2)	0.8243 (6)	0.0786 (18)
H18A	0.6628	0.2997	0.8065	0.118*
H18B	0.7025	0.3531	0.9001	0.118*
H18C	0.7663	0.3413	0.8163	0.118*
C19	0.3926 (3)	0.34377 (15)	0.9308 (3)	0.0293 (8)
H19	0.3947	0.3903	0.9141	0.035*
C20	0.2820 (3)	0.32984 (19)	0.9340 (3)	0.0459 (10)
H20A	0.2296	0.3379	0.8613	0.069*
H20B	0.2672	0.3576	0.9884	0.069*
H20C	0.2778	0.285	0.9542	0.069*
C21	0.4770 (4)	0.33255 (18)	1.0423 (3)	0.0450 (10)
H21A	0.4781	0.2872	1.0615	0.068*
H21B	0.4605	0.3582	1.0981	0.068*
H21C	0.5468	0.345	1.039	0.068*
C22	0.4165 (3)	0.23797 (14)	0.8507 (3)	0.0277 (7)
H22	0.4042	0.2273	0.9211	0.033*
C23	0.5224 (3)	0.20904 (17)	0.8573 (3)	0.0386 (9)
H23A	0.5361	0.2168	0.7882	0.058*
H23B	0.5208	0.1629	0.8698	0.058*
H23C	0.5789	0.2287	0.9182	0.058*
C24	0.3262 (3)	0.20786 (17)	0.7590 (3)	0.0414 (9)
H24A	0.2583	0.2255	0.7596	0.062*
H24B	0.3266	0.1615	0.7699	0.062*
H24C	0.3353	0.2171	0.6881	0.062*
N1	−0.08069 (19)	0.35006 (11)	0.3314 (2)	0.0204 (6)
N2	−0.00033 (19)	0.44163 (12)	0.2262 (2)	0.0206 (5)
N3	0.52404 (19)	0.40146 (11)	0.7648 (2)	0.0212 (6)
N4	0.4172 (2)	0.30869 (11)	0.8429 (2)	0.0216 (6)
P1	0.03033 (6)	0.37788 (4)	0.31167 (6)	0.01830 (19)
P2	0.10621 (6)	0.42397 (4)	0.47668 (6)	0.0214 (2)
P3	0.43260 (6)	0.34204 (4)	0.72996 (6)	0.01890 (19)
P4	0.28812 (6)	0.40449 (4)	0.66843 (6)	0.0212 (2)
P5	0.27184 (6)	0.39792 (4)	0.49234 (7)	0.0271 (2)
P6	0.18012 (7)	0.33459 (4)	0.55847 (7)	0.0273 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0242 (17)	0.0277 (17)	0.0323 (18)	−0.0045 (14)	0.0146 (14)	−0.0053 (14)
C2	0.0264 (18)	0.0326 (19)	0.048 (2)	−0.0002 (14)	0.0157 (16)	−0.0008 (17)
C3	0.040 (2)	0.042 (2)	0.034 (2)	−0.0085 (16)	0.0225 (17)	−0.0024 (16)
C4	0.0321 (18)	0.0203 (16)	0.0359 (19)	−0.0082 (14)	0.0152 (15)	−0.0044 (14)
C5	0.045 (2)	0.035 (2)	0.035 (2)	−0.0159 (17)	0.0078 (17)	−0.0111 (16)
C6	0.049 (2)	0.0227 (19)	0.068 (3)	−0.0010 (16)	0.022 (2)	−0.0028 (18)
C7	0.0300 (18)	0.0221 (16)	0.0245 (17)	0.0012 (13)	0.0095 (14)	0.0031 (13)
C8	0.047 (2)	0.0247 (18)	0.036 (2)	−0.0013 (15)	0.0143 (17)	−0.0010 (15)
C9	0.0302 (19)	0.0337 (19)	0.0316 (19)	0.0067 (15)	0.0084 (15)	0.0076 (15)
C10	0.0279 (18)	0.0296 (18)	0.0240 (17)	0.0015 (14)	0.0110 (14)	0.0068 (14)
C11	0.060 (3)	0.042 (2)	0.031 (2)	−0.0044 (18)	0.0265 (18)	−0.0018 (17)
C12	0.032 (2)	0.058 (3)	0.037 (2)	−0.0070 (18)	0.0149 (17)	0.0092 (18)
C13	0.0190 (16)	0.0261 (17)	0.0309 (18)	−0.0033 (13)	0.0088 (13)	−0.0045 (14)
C14	0.0286 (19)	0.0298 (19)	0.043 (2)	−0.0019 (15)	0.0053 (16)	0.0037 (16)
C15	0.0345 (19)	0.036 (2)	0.0292 (18)	−0.0080 (15)	0.0100 (15)	−0.0089 (16)
C16	0.0242 (18)	0.037 (2)	0.056 (2)	−0.0031 (15)	0.0214 (17)	−0.0123 (18)
C17	0.072 (3)	0.140 (5)	0.092 (4)	−0.054 (3)	0.072 (3)	−0.068 (4)
C18	0.029 (2)	0.052 (3)	0.155 (6)	0.017 (2)	0.030 (3)	0.012 (3)
C19	0.049 (2)	0.0192 (16)	0.0272 (18)	0.0066 (15)	0.0228 (16)	0.0025 (13)
C20	0.060 (3)	0.042 (2)	0.052 (2)	0.0215 (19)	0.041 (2)	0.0212 (19)
C21	0.080 (3)	0.031 (2)	0.0234 (19)	−0.003 (2)	0.0167 (19)	−0.0030 (15)
C22	0.043 (2)	0.0166 (16)	0.0236 (17)	0.0040 (14)	0.0108 (14)	0.0033 (13)
C23	0.054 (2)	0.0259 (18)	0.037 (2)	0.0158 (16)	0.0170 (18)	0.0051 (16)
C24	0.061 (2)	0.0256 (19)	0.037 (2)	−0.0106 (17)	0.0155 (19)	−0.0005 (16)
N1	0.0239 (14)	0.0173 (13)	0.0229 (13)	−0.0054 (10)	0.0116 (11)	−0.0028 (10)
N2	0.0233 (13)	0.0207 (13)	0.0188 (13)	−0.0001 (10)	0.0082 (10)	0.0049 (10)
N3	0.0172 (13)	0.0207 (13)	0.0258 (14)	−0.0002 (10)	0.0074 (11)	−0.0030 (11)
N4	0.0292 (14)	0.0180 (13)	0.0193 (13)	0.0038 (11)	0.0105 (11)	−0.0003 (10)
P1	0.0177 (4)	0.0201 (4)	0.0168 (4)	0.0002 (3)	0.0052 (3)	0.0026 (3)
P2	0.0183 (4)	0.0241 (4)	0.0195 (4)	0.0007 (3)	0.0032 (3)	0.0009 (3)
P3	0.0197 (4)	0.0193 (4)	0.0169 (4)	0.0014 (3)	0.0050 (3)	−0.0009 (3)
P4	0.0187 (4)	0.0240 (4)	0.0191 (4)	0.0022 (3)	0.0037 (3)	0.0001 (3)
P5	0.0201 (4)	0.0415 (5)	0.0195 (4)	0.0020 (4)	0.0063 (3)	0.0047 (4)
P6	0.0255 (5)	0.0248 (4)	0.0251 (4)	−0.0041 (3)	−0.0003 (4)	0.0043 (4)

Geometric parameters (Å, º) top

C1—N1	1.479 (4)	C14—H14C	0.98
C1—C3	1.516 (5)	C15—H15A	0.98
C1—C2	1.529 (5)	C15—H15B	0.98
C1—H1	1	C15—H15C	0.98
C2—H2A	0.98	C16—N3	1.474 (4)
C2—H2B	0.98	C16—C17	1.505 (6)
C2—H2C	0.98	C16—C18	1.534 (6)
C3—H3A	0.98	C16—H16	1
C3—H3B	0.98	C17—H17A	0.98
C3—H3C	0.98	C17—H17B	0.98
C4—N1	1.479 (4)	C17—H17C	0.98
C4—C6	1.519 (5)	C18—H18A	0.98
C4—C5	1.526 (5)	C18—H18B	0.98
C4—H4	1	C18—H18C	0.98
C5—H5A	0.98	C19—N4	1.476 (4)
C5—H5B	0.98	C19—C20	1.516 (5)
C5—H5C	0.98	C19—C21	1.521 (5)
C6—H6A	0.98	C19—H19	1
C6—H6B	0.98	C20—H20A	0.98
C6—H6C	0.98	C20—H20B	0.98
C7—N2	1.472 (4)	C20—H20C	0.98
C7—C9	1.522 (4)	C21—H21A	0.98
C7—C8	1.525 (4)	C21—H21B	0.98
C7—H7	1	C21—H21C	0.98
C8—H8A	0.98	C22—N4	1.484 (4)
C8—H8B	0.98	C22—C23	1.512 (5)
C8—H8C	0.98	C22—C24	1.517 (5)
C9—H9A	0.98	C22—H22	1
C9—H9B	0.98	C23—H23A	0.98
C9—H9C	0.98	C23—H23B	0.98
C10—N2	1.469 (4)	C23—H23C	0.98
C10—C11	1.521 (5)	C24—H24A	0.98
C10—C12	1.531 (5)	C24—H24B	0.98
C10—H10	1	C24—H24C	0.98
C11—H11A	0.98	N1—P1	1.686 (2)
C11—H11B	0.98	N2—P1	1.692 (2)
C11—H11C	0.98	N3—P3	1.695 (2)
C12—H12A	0.98	N4—P3	1.688 (3)
C12—H12B	0.98	P1—P2	2.2482 (11)
C12—H12C	0.98	P2—P6	2.2121 (11)
C13—N3	1.477 (4)	P2—P5	2.2176 (11)
C13—C15	1.520 (4)	P3—P4	2.2438 (11)
C13—C14	1.522 (5)	P4—P6	2.2070 (11)
C13—H13	1	P4—P5	2.2123 (11)
C14—H14A	0.98	P5—P6	2.1610 (12)
C14—H14B	0.98

N1—C1—C3	111.6 (3)	C13—C15—H15C	109.5
N1—C1—C2	113.5 (3)	H15A—C15—H15C	109.5
C3—C1—C2	110.5 (3)	H15B—C15—H15C	109.5
N1—C1—H1	107	N3—C16—C17	112.3 (3)
C3—C1—H1	107	N3—C16—C18	111.9 (3)
C2—C1—H1	107	C17—C16—C18	112.3 (4)
C1—C2—H2A	109.5	N3—C16—H16	106.6
C1—C2—H2B	109.5	C17—C16—H16	106.6
H2A—C2—H2B	109.5	C18—C16—H16	106.6
C1—C2—H2C	109.5	C16—C17—H17A	109.5
H2A—C2—H2C	109.5	C16—C17—H17B	109.5
H2B—C2—H2C	109.5	H17A—C17—H17B	109.5
C1—C3—H3A	109.5	C16—C17—H17C	109.5
C1—C3—H3B	109.5	H17A—C17—H17C	109.5
H3A—C3—H3B	109.5	H17B—C17—H17C	109.5
C1—C3—H3C	109.5	C16—C18—H18A	109.5
H3A—C3—H3C	109.5	C16—C18—H18B	109.5
H3B—C3—H3C	109.5	H18A—C18—H18B	109.5
N1—C4—C6	112.9 (3)	C16—C18—H18C	109.5
N1—C4—C5	111.7 (3)	H18A—C18—H18C	109.5
C6—C4—C5	111.6 (3)	H18B—C18—H18C	109.5
N1—C4—H4	106.7	N4—C19—C20	112.9 (3)
C6—C4—H4	106.7	N4—C19—C21	111.5 (3)
C5—C4—H4	106.7	C20—C19—C21	111.5 (3)
C4—C5—H5A	109.5	N4—C19—H19	106.8
C4—C5—H5B	109.5	C20—C19—H19	106.8
H5A—C5—H5B	109.5	C21—C19—H19	106.8
C4—C5—H5C	109.5	C19—C20—H20A	109.5
H5A—C5—H5C	109.5	C19—C20—H20B	109.5
H5B—C5—H5C	109.5	H20A—C20—H20B	109.5
C4—C6—H6A	109.5	C19—C20—H20C	109.5
C4—C6—H6B	109.5	H20A—C20—H20C	109.5
H6A—C6—H6B	109.5	H20B—C20—H20C	109.5
C4—C6—H6C	109.5	C19—C21—H21A	109.5
H6A—C6—H6C	109.5	C19—C21—H21B	109.5
H6B—C6—H6C	109.5	H21A—C21—H21B	109.5
N2—C7—C9	111.1 (3)	C19—C21—H21C	109.5
N2—C7—C8	112.9 (3)	H21A—C21—H21C	109.5
C9—C7—C8	111.7 (3)	H21B—C21—H21C	109.5
N2—C7—H7	106.9	N4—C22—C23	112.1 (3)
C9—C7—H7	106.9	N4—C22—C24	112.5 (3)
C8—C7—H7	106.9	C23—C22—C24	111.3 (3)
C7—C8—H8A	109.5	N4—C22—H22	106.8
C7—C8—H8B	109.5	C23—C22—H22	106.8
H8A—C8—H8B	109.5	C24—C22—H22	106.8
C7—C8—H8C	109.5	C22—C23—H23A	109.5
H8A—C8—H8C	109.5	C22—C23—H23B	109.5
H8B—C8—H8C	109.5	H23A—C23—H23B	109.5
C7—C9—H9A	109.5	C22—C23—H23C	109.5
C7—C9—H9B	109.5	H23A—C23—H23C	109.5
H9A—C9—H9B	109.5	H23B—C23—H23C	109.5
C7—C9—H9C	109.5	C22—C24—H24A	109.5
H9A—C9—H9C	109.5	C22—C24—H24B	109.5
H9B—C9—H9C	109.5	H24A—C24—H24B	109.5
N2—C10—C11	113.0 (3)	C22—C24—H24C	109.5
N2—C10—C12	111.6 (3)	H24A—C24—H24C	109.5
C11—C10—C12	111.1 (3)	H24B—C24—H24C	109.5
N2—C10—H10	106.9	C1—N1—C4	115.1 (2)
C11—C10—H10	106.9	C1—N1—P1	127.1 (2)
C12—C10—H10	106.9	C4—N1—P1	117.8 (2)
C10—C11—H11A	109.5	C10—N2—C7	117.2 (2)
C10—C11—H11B	109.5	C10—N2—P1	118.3 (2)
H11A—C11—H11B	109.5	C7—N2—P1	124.3 (2)
C10—C11—H11C	109.5	C16—N3—C13	114.7 (2)
H11A—C11—H11C	109.5	C16—N3—P3	118.6 (2)
H11B—C11—H11C	109.5	C13—N3—P3	126.7 (2)
C10—C12—H12A	109.5	C19—N4—C22	115.9 (2)
C10—C12—H12B	109.5	C19—N4—P3	125.3 (2)
H12A—C12—H12B	109.5	C22—N4—P3	118.4 (2)
C10—C12—H12C	109.5	N1—P1—N2	109.62 (12)
H12A—C12—H12C	109.5	N1—P1—P2	98.49 (9)
H12B—C12—H12C	109.5	N2—P1—P2	102.35 (9)
N3—C13—C15	112.9 (3)	P6—P2—P5	58.40 (4)
N3—C13—C14	112.1 (3)	P6—P2—P1	94.47 (4)
C15—C13—C14	111.3 (3)	P5—P2—P1	95.90 (4)
N3—C13—H13	106.7	N4—P3—N3	110.93 (13)
C15—C13—H13	106.7	N4—P3—P4	102.15 (9)
C14—C13—H13	106.7	N3—P3—P4	97.12 (9)
C13—C14—H14A	109.5	P6—P4—P5	58.55 (4)
C13—C14—H14B	109.5	P6—P4—P3	98.15 (4)
H14A—C14—H14B	109.5	P5—P4—P3	96.17 (4)
C13—C14—H14C	109.5	P6—P5—P4	60.60 (4)
H14A—C14—H14C	109.5	P6—P5—P2	60.68 (4)
H14B—C14—H14C	109.5	P4—P5—P2	80.46 (4)
C13—C15—H15A	109.5	P5—P6—P4	60.85 (4)
C13—C15—H15B	109.5	P5—P6—P2	60.93 (4)
H15A—C15—H15B	109.5	P4—P6—P2	80.70 (4)

C3—C1—N1—C4	63.7 (3)	C4—N1—P1—P2	−147.9 (2)
C2—C1—N1—C4	−62.0 (3)	C10—N2—P1—N1	−138.7 (2)
C3—C1—N1—P1	−115.5 (3)	C7—N2—P1—N1	47.2 (3)
C2—C1—N1—P1	118.9 (3)	C10—N2—P1—P2	117.5 (2)
C6—C4—N1—C1	−126.1 (3)	C7—N2—P1—P2	−56.6 (2)
C5—C4—N1—C1	107.2 (3)	N1—P1—P2—P6	84.13 (9)
C6—C4—N1—P1	53.1 (3)	N2—P1—P2—P6	−163.53 (9)
C5—C4—N1—P1	−73.6 (3)	N1—P1—P2—P5	142.77 (9)
C11—C10—N2—C7	−125.6 (3)	N2—P1—P2—P5	−104.88 (10)
C12—C10—N2—C7	108.4 (3)	C19—N4—P3—N3	53.6 (3)
C11—C10—N2—P1	59.9 (3)	C22—N4—P3—N3	−133.4 (2)
C12—C10—N2—P1	−66.2 (3)	C19—N4—P3—P4	−49.0 (3)
C9—C7—N2—C10	66.3 (3)	C22—N4—P3—P4	124.0 (2)
C8—C7—N2—C10	−60.1 (4)	C16—N3—P3—N4	111.4 (2)
C9—C7—N2—P1	−119.6 (3)	C13—N3—P3—N4	−71.5 (3)
C8—C7—N2—P1	114.1 (3)	C16—N3—P3—P4	−142.6 (2)
C17—C16—N3—C13	−120.2 (4)	C13—N3—P3—P4	34.5 (3)
C18—C16—N3—C13	112.5 (4)	N4—P3—P4—P6	−90.61 (10)
C17—C16—N3—P3	57.3 (4)	N3—P3—P4—P6	156.11 (10)
C18—C16—N3—P3	−70.1 (4)	N4—P3—P4—P5	−149.63 (10)
C15—C13—N3—C16	−63.2 (4)	N3—P3—P4—P5	97.09 (10)
C14—C13—N3—C16	63.5 (3)	P3—P4—P5—P6	95.80 (4)
C15—C13—N3—P3	119.6 (3)	P6—P4—P5—P2	61.62 (4)
C14—C13—N3—P3	−113.7 (3)	P3—P4—P5—P2	157.42 (4)
C20—C19—N4—C22	−61.8 (4)	P1—P2—P5—P6	−91.63 (4)
C21—C19—N4—C22	64.7 (4)	P6—P2—P5—P4	−61.54 (4)
C20—C19—N4—P3	111.4 (3)	P1—P2—P5—P4	−153.17 (4)
C21—C19—N4—P3	−122.2 (3)	P2—P5—P6—P4	−95.64 (4)
C23—C22—N4—C19	−121.2 (3)	P4—P5—P6—P2	95.64 (4)
C24—C22—N4—C19	112.5 (3)	P3—P4—P6—P5	−92.27 (4)
C23—C22—N4—P3	65.1 (3)	P5—P4—P6—P2	−61.81 (4)
C24—C22—N4—P3	−61.2 (3)	P3—P4—P6—P2	−154.08 (4)
C1—N1—P1—N2	−75.2 (3)	P1—P2—P6—P5	94.19 (4)
C4—N1—P1—N2	105.7 (2)	P5—P2—P6—P4	61.73 (4)
C1—N1—P1—P2	31.2 (3)	P1—P2—P6—P4	155.91 (4)

Experimental details

Crystal data
Chemical formula	C₂₄H₅₆N₄P₆
M_r	586.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	13.3307 (5), 20.9304 (7), 12.8939 (5)
β (°)	109.349 (4)
V (Å³)	3394.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.46 × 0.14 × 0.06

Data collection
Diffractometer	Oxford Diffraction KM-4 CCD diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.955, 1.045
No. of measured, independent and observed [I > 2σ(I)] reflections	6310, 6310, 4727
R_int	0
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.136, 1.04
No. of reflections	6310
No. of parameters	324
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.51

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

The work was undertaken with financial support from the Polish Ministry of Science and Higher Education (grant No. N N204 271535).

References

Bezombes, J.-P., Hitchcock, P. B., Lappert, M. F. & Nycz, J. E. (2004). Dalton Trans. pp. 499–501. Web of Science CSD CrossRef PubMed Google Scholar
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