2,4-Bis[bis(diisopropyl-amino)-phos-phanyl]-1,2,3,4-tetra-phospha-bicyclo[1.1.0]butane.

The title compound, C(24)H(56)N(4)P(6) or ((i)Pr(2)N)(2)P-P(4)-P(N(i)Pr(2))(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 = 586.55

Monoclinic,

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 ▶) T min = 0.954, T max = 1.045

6310 measured reflections

6310 independent reflections

4727 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.136

S = 1.04

6310 reflections

324 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); 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 ▶).

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

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

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

C24H56N4P6	F000 = 1272
Mr = 586.55	Dx = 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 = 2.5–32.4º
b = 20.9304 (7) Å	µ = 0.34 mm−1
c = 12.8939 (5) Å	T = 120 (2) K
β = 109.349 (4)º	Prism, colourless
V = 3394.4 (2) Å3	0.46 × 0.14 × 0.06 mm
Z = 4

Oxford Diffraction KM-4 CCD diffractometer	6310 independent reflections
Monochromator: graphite	4727 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm-1	Rint = 0
T = 120(2) K	θmax = 25.5º
ω scans, 0.75 deg width	θmin = 2.5º
Absorption correction: analytical(CrysAlis RED; Oxford Diffraction, 2006)	h = −16→16
Tmin = 0.955, Tmax = 1.045	k = −25→25
6310 measured reflections	l = −13→15

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) = 0.136	w = 1/[σ2(Fo2) + (0.0841P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
6310 reflections	Δρmax = 0.61 e Å−3
324 parameters	Δρmin = −0.51 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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

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

	x	y	z	Uiso*/Ueq
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)

	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)

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)