N-Diphenyl­phosphanyl-N-{[diphen­yl(2-pyridyl­imino)-λ5-phosphan­yl]meth­yl}pyridin-2-amine

Peng, X.; Yuan, Y.; Chen, X.

doi:10.1107/S1600536811037007

N-Diphenylphosphanyl-N-{[diphenyl(2-pyridylimino)-λ⁵-phosphanyl]methyl}pyridin-2-amine

In the title compound, C₃₅H₃₀N₄P₂, the diphenylphosphanyl and diphenyl(2-pyridylimino)-λ⁵-phosphanyl groups are attached to the central methyl C atom with a P—C—N angle of 114.09 (16)°. The molecules stack along the b axis and interconnect through C—H(pyridyl)

N(pyridyl) interactions, forming an infinite chain structure. The parallel chains are further interconnected via C—H(benzene)

N(amino) and C—H(benzene)

π interactions, forming a three-dimensional framework.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811037007/ez2257sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811037007/ez2257Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536811037007/ez2257Isup3.cml Supplementary material

CCDC reference: 850586

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.060
wR factor = 0.126
Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ...          1
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW .gt. 10 Outliers .          1

Alert level C
PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...        3.8 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0049 Ang
PLAT480_ALERT_4_C Long H...A H-Bond Reported H32    ..  N2      ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21    ..  N3      ..       2.73 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         12

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.       6.20
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   2 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
   5 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Bis(iminophosphorany)methane and its derivatives are attracting much attention due to their flexible coordination behavior (Avis et al., 1996, 1997) and the catalytic activity of their transition metal complexes (Hill & Hitchcock, 2002; Ma et al., 2011).Herein, we report the crystal structure of a mono-phosphinimine, namely ((N-2-pyridylimino)diphenylphosphoranyl)(N-2-pyridyl-N-diphenylphosphinoamino) methane.

In the crystal structure of the title compound, the (N-2-pyridylimino)diphenylphosphoranyl and the N-2-pyridyl-N-diphenylphosphinoamino groups are attached to the methyl with a P2—C6—N1 angle of 114.09 (2)°. The P2=N3 bond length of 1.593 (2) Å is comparable to that of P=N distances of 1.555 (3) and 1.573 (3) Å in bis(iminophosphorany)methane (Hill & Hitchcock, 2002). The molecules stack along the b axis and interconnect through C32—H32(pyridyl)···N2ⁱ(pyridyl) interactions (D···A 3.577 (3)Å, Table 1), forming an infinite chain. These parallel chains are further interconnected via C21—H21(benzene)··· N3ⁱⁱ(amino) and C28—H28(benzene)···Cgⁱⁱⁱ interactions to form a three-dimensional framework (Cg represents the C7 to C12 benzene ring, Table 1). Symmetry codes: i: x, y+1, z; ii: x, -y-1, z-0.5; iii: -x, y-1, -z+0.5.

Related literature top

For transition metal complexes with iminophosphoranyl derivatives, see: Avis et al. (1996, 1997). For the catalytic activity of bis(iminophosphoranyl)methane and its derivatives, see: Hill & Hitchcock (2002); Ma et al. (2011). For the crystal structure of an analogous compound, see: Hill & Hitchcock (2002).

Experimental top

To a solution of 0.4g (0.1 mmol) N-((pyridin-2-ylamino)methyl)pyridind-2-amine in 40 ml CH₂Cl₂ at room temperature a solution of 0.45 g (0.2 mmol) chlorodiphenylphosphine in the presence of Et₃N in 10 ml toluene was added dropwise, during which N₂ gas evolved. After 2 h stirring the resultant yellow solution was evaporated, giving a white powder. The white powder was then separated and purified by column chromatography on silica gel (column of 2 cm diameter, eluent: dichloromethane/acetate = 95:5, v/v), and the title compound was obtained in 60% yield. Orange crystals of the title compound having average dimensions of 0.40 × 0.30 × 0.20 mm³ were obtained by slow evaporation from a solution of dichloromethane/N,N-dimethylformamide 1/1 (v/v).

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The atom-numbering scheme of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are omitted for clarity.
	Fig. 2. A view of the packing of the title compound. The red dashed lines represent C32—H32(pyridyl)···N2ⁱ(pyridyl) interactions that connect the molecules along the b axis (symmetry code: i: -x+1, -y, -z). The other interactions are omitted for clarity. Color codes: Green P, Blue N,Gray C.

N-Diphenylphosphanyl-N-{[diphenyl(2-pyridylimino)-λ⁵- phosphanyl]methyl}pyridin-2-amine top

Crystal data top

C₃₅H₃₀N₄P₂	F(000) = 2384
M_r = 568.57	D_x = 1.272 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.505 (7) Å	Cell parameters from 241 reflections
b = 9.142 (3) Å	θ = 2.1–26.3°
c = 29.606 (9) Å	µ = 0.18 mm⁻¹
β = 102.877 (5)°	T = 293 K
V = 5938 (3) Å³	Block, orange
Z = 8	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	6035 independent reflections
Radiation source: fine-focus sealed tube	4510 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω scans	θ_max = 26.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −27→28
T_min = 0.753, T_max = 1.000	k = −11→9
16500 measured reflections	l = −36→33

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0394P)² + 6.1976P] where P = (F_o² + 2F_c²)/3
6035 reflections	(Δ/σ)_max < 0.001
370 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₃₅H₃₀N₄P₂	V = 5938 (3) Å³
M_r = 568.57	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.505 (7) Å	µ = 0.18 mm⁻¹
b = 9.142 (3) Å	T = 293 K
c = 29.606 (9) Å	0.40 × 0.30 × 0.20 mm
β = 102.877 (5)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	6035 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	4510 reflections with I > 2σ(I)
T_min = 0.753, T_max = 1.000	R_int = 0.041
16500 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.15	Δρ_max = 0.39 e Å⁻³
6035 reflections	Δρ_min = −0.28 e Å⁻³
370 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
P1	−0.01563 (3)	0.63607 (8)	0.14930 (2)	0.03712 (18)
P2	0.16356 (3)	0.73616 (7)	0.14753 (2)	0.02853 (16)
N1	0.05842 (8)	0.5832 (2)	0.15430 (7)	0.0323 (5)
N2	0.11485 (10)	0.3691 (3)	0.17411 (7)	0.0408 (5)
N3	0.15628 (10)	0.9082 (2)	0.13974 (7)	0.0357 (5)
N4	0.14031 (12)	0.8766 (3)	0.05916 (7)	0.0501 (6)
C1	0.08083 (10)	0.4717 (3)	0.18710 (8)	0.0320 (6)
C2	0.06822 (12)	0.4749 (3)	0.23102 (9)	0.0411 (6)
H2	0.0448	0.5498	0.2393	0.049*
C3	0.09084 (13)	0.3661 (4)	0.26186 (10)	0.0487 (7)
H3	0.0828	0.3661	0.2914	0.058*
C4	0.12536 (14)	0.2572 (4)	0.24880 (10)	0.0550 (8)
H4	0.1410	0.1817	0.2690	0.066*
C5	0.13608 (14)	0.2634 (4)	0.20499 (10)	0.0548 (8)
H5	0.1595	0.1896	0.1961	0.066*
C6	0.09627 (10)	0.6230 (3)	0.12172 (8)	0.0320 (6)
H6A	0.0713	0.6761	0.0960	0.038*
H6B	0.1101	0.5341	0.1094	0.038*
C7	−0.01288 (12)	0.8317 (3)	0.13863 (11)	0.0451 (7)
C8	−0.01064 (15)	0.9233 (4)	0.17666 (13)	0.0719 (11)
H8	−0.0121	0.8834	0.2053	0.086*
C9	−0.0062 (2)	1.0736 (5)	0.1719 (2)	0.110 (2)
H9	−0.0043	1.1339	0.1975	0.132*
C10	−0.00475 (19)	1.1337 (5)	0.1302 (2)	0.113 (2)
H10	−0.0017	1.2345	0.1273	0.135*
C11	−0.00772 (16)	1.0462 (5)	0.09285 (19)	0.0899 (14)
H11	−0.0070	1.0877	0.0643	0.108*
C12	−0.01182 (13)	0.8961 (4)	0.09660 (13)	0.0601 (9)
H12	−0.0139	0.8377	0.0706	0.072*
C13	−0.05681 (12)	0.5681 (3)	0.09276 (9)	0.0415 (6)
C14	−0.03331 (15)	0.4781 (4)	0.06367 (11)	0.0565 (8)
H14	0.0080	0.4557	0.0708	0.068*
C15	−0.07070 (19)	0.4202 (4)	0.02363 (12)	0.0731 (11)
H15	−0.0541	0.3603	0.0042	0.088*
C16	−0.1314 (2)	0.4510 (5)	0.01285 (13)	0.0787 (12)
H16	−0.1563	0.4120	−0.0138	0.094*
C17	−0.15543 (17)	0.5391 (5)	0.04118 (15)	0.0806 (12)
H17	−0.1969	0.5602	0.0338	0.097*
C18	−0.11885 (14)	0.5978 (4)	0.08082 (12)	0.0607 (9)
H18	−0.1360	0.6581	0.0998	0.073*
C19	0.17852 (10)	0.7135 (3)	0.20950 (8)	0.0297 (5)
C20	0.21447 (11)	0.6004 (3)	0.23177 (8)	0.0373 (6)
H20	0.2324	0.5353	0.2147	0.045*
C21	0.22379 (12)	0.5835 (4)	0.27910 (9)	0.0472 (7)
H21	0.2477	0.5070	0.2939	0.057*
C22	0.19752 (14)	0.6807 (4)	0.30441 (9)	0.0545 (8)
H22	0.2040	0.6698	0.3364	0.065*
C23	0.16185 (14)	0.7935 (4)	0.28284 (10)	0.0534 (8)
H23	0.1442	0.8584	0.3002	0.064*
C24	0.15210 (12)	0.8109 (3)	0.23526 (9)	0.0403 (6)
H24	0.1280	0.8874	0.2207	0.048*
C25	0.22768 (11)	0.6569 (3)	0.12830 (8)	0.0323 (6)
C26	0.23091 (12)	0.5109 (3)	0.11729 (9)	0.0423 (7)
H26	0.1993	0.4478	0.1195	0.051*
C27	0.28149 (14)	0.4588 (4)	0.10292 (10)	0.0559 (8)
H27	0.2831	0.3611	0.0945	0.067*
C28	0.32934 (14)	0.5506 (4)	0.10102 (11)	0.0604 (9)
H28	0.3637	0.5143	0.0923	0.072*
C29	0.32629 (14)	0.6950 (5)	0.11197 (12)	0.0644 (10)
H29	0.3586	0.7570	0.1105	0.077*
C30	0.27536 (12)	0.7498 (4)	0.12529 (10)	0.0498 (7)
H30	0.2732	0.8487	0.1322	0.060*
C31	0.14809 (12)	0.9659 (3)	0.09597 (8)	0.0365 (6)
C32	0.14870 (16)	1.1179 (3)	0.09068 (10)	0.0561 (8)
H32	0.1532	1.1783	0.1165	0.067*
C33	0.14268 (19)	1.1772 (4)	0.04781 (11)	0.0737 (11)
H33	0.1427	1.2782	0.0440	0.088*
C34	0.1366 (2)	1.0861 (4)	0.01011 (11)	0.0878 (14)
H34	0.1333	1.1235	−0.0196	0.105*
C35	0.1355 (2)	0.9390 (4)	0.01768 (10)	0.0770 (12)
H35	0.1310	0.8776	−0.0079	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0288 (3)	0.0405 (4)	0.0426 (4)	0.0037 (3)	0.0091 (3)	0.0017 (3)
P2	0.0308 (3)	0.0285 (4)	0.0267 (3)	0.0002 (3)	0.0074 (2)	0.0001 (3)
N1	0.0263 (10)	0.0357 (13)	0.0360 (11)	0.0026 (9)	0.0094 (8)	0.0051 (9)
N2	0.0424 (12)	0.0394 (14)	0.0400 (12)	0.0099 (11)	0.0078 (10)	−0.0005 (10)
N3	0.0459 (12)	0.0303 (12)	0.0310 (11)	0.0001 (10)	0.0089 (9)	−0.0006 (9)
N4	0.0818 (18)	0.0345 (14)	0.0315 (12)	−0.0078 (13)	0.0071 (11)	−0.0018 (10)
C1	0.0263 (12)	0.0317 (14)	0.0379 (14)	−0.0039 (11)	0.0066 (10)	−0.0003 (11)
C2	0.0362 (14)	0.0461 (18)	0.0442 (15)	0.0032 (13)	0.0159 (12)	0.0044 (13)
C3	0.0500 (17)	0.056 (2)	0.0418 (16)	−0.0007 (15)	0.0136 (13)	0.0111 (14)
C4	0.0609 (19)	0.0467 (19)	0.0528 (18)	0.0083 (16)	0.0030 (15)	0.0159 (15)
C5	0.0578 (18)	0.048 (2)	0.0556 (18)	0.0198 (16)	0.0067 (14)	0.0010 (15)
C6	0.0301 (12)	0.0380 (15)	0.0281 (12)	−0.0013 (11)	0.0070 (10)	0.0008 (11)
C7	0.0306 (14)	0.0343 (16)	0.0661 (19)	0.0075 (12)	0.0013 (13)	−0.0053 (14)
C8	0.058 (2)	0.062 (2)	0.082 (2)	0.0150 (18)	−0.0128 (18)	−0.029 (2)
C9	0.079 (3)	0.064 (3)	0.156 (5)	0.021 (2)	−0.042 (3)	−0.051 (3)
C10	0.066 (3)	0.038 (2)	0.201 (6)	−0.006 (2)	−0.038 (3)	0.002 (3)
C11	0.048 (2)	0.055 (3)	0.157 (4)	0.0017 (19)	0.003 (2)	0.035 (3)
C12	0.0427 (17)	0.046 (2)	0.090 (3)	0.0077 (14)	0.0112 (16)	0.0131 (18)
C13	0.0417 (15)	0.0305 (15)	0.0494 (16)	−0.0043 (12)	0.0041 (12)	0.0082 (13)
C14	0.0552 (18)	0.050 (2)	0.063 (2)	−0.0137 (16)	0.0117 (15)	−0.0091 (16)
C15	0.099 (3)	0.059 (2)	0.060 (2)	−0.030 (2)	0.014 (2)	−0.0107 (18)
C16	0.095 (3)	0.061 (3)	0.062 (2)	−0.032 (2)	−0.020 (2)	0.013 (2)
C17	0.059 (2)	0.070 (3)	0.093 (3)	−0.007 (2)	−0.026 (2)	0.014 (2)
C18	0.0442 (17)	0.054 (2)	0.076 (2)	0.0047 (15)	−0.0049 (15)	0.0022 (17)
C19	0.0283 (12)	0.0321 (14)	0.0286 (12)	−0.0041 (10)	0.0059 (9)	−0.0005 (10)
C20	0.0334 (13)	0.0443 (17)	0.0342 (14)	0.0005 (12)	0.0073 (11)	0.0013 (12)
C21	0.0410 (15)	0.057 (2)	0.0401 (15)	−0.0001 (14)	0.0013 (12)	0.0097 (14)
C22	0.0610 (19)	0.073 (2)	0.0270 (14)	−0.0051 (18)	0.0056 (13)	0.0026 (15)
C23	0.0640 (19)	0.061 (2)	0.0374 (16)	0.0020 (17)	0.0171 (14)	−0.0099 (15)
C24	0.0469 (15)	0.0382 (16)	0.0357 (14)	0.0028 (13)	0.0088 (12)	−0.0018 (12)
C25	0.0311 (12)	0.0385 (16)	0.0284 (12)	0.0005 (11)	0.0085 (10)	0.0032 (11)
C26	0.0397 (14)	0.0426 (18)	0.0480 (16)	0.0052 (13)	0.0167 (12)	0.0013 (13)
C27	0.0609 (19)	0.053 (2)	0.0583 (19)	0.0199 (17)	0.0230 (15)	0.0017 (15)
C28	0.0475 (18)	0.085 (3)	0.0563 (19)	0.0178 (18)	0.0281 (15)	0.0078 (18)
C29	0.0432 (17)	0.084 (3)	0.073 (2)	−0.0059 (17)	0.0275 (16)	0.005 (2)
C30	0.0432 (15)	0.0495 (19)	0.0613 (19)	−0.0042 (14)	0.0211 (14)	−0.0022 (15)
C31	0.0419 (14)	0.0353 (16)	0.0309 (13)	−0.0026 (12)	0.0050 (11)	−0.0006 (11)
C32	0.097 (2)	0.0338 (17)	0.0373 (16)	−0.0079 (17)	0.0133 (16)	−0.0033 (13)
C33	0.133 (3)	0.0322 (18)	0.051 (2)	−0.006 (2)	0.010 (2)	0.0100 (15)
C34	0.167 (4)	0.055 (2)	0.0338 (18)	−0.021 (3)	0.006 (2)	0.0096 (16)
C35	0.146 (4)	0.049 (2)	0.0304 (16)	−0.021 (2)	0.0057 (18)	−0.0011 (15)

Geometric parameters (Å, º) top

P1—N1	1.710 (2)	C14—H14	0.9300
P1—C7	1.820 (3)	C15—C16	1.362 (6)
P1—C13	1.832 (3)	C15—H15	0.9300
P2—N3	1.593 (2)	C16—C17	1.359 (6)
P2—C19	1.802 (2)	C16—H16	0.9300
P2—C25	1.816 (2)	C17—C18	1.383 (5)
P2—C6	1.853 (2)	C17—H17	0.9300
N1—C1	1.421 (3)	C18—H18	0.9300
N1—C6	1.468 (3)	C19—C20	1.386 (3)
N2—C1	1.321 (3)	C19—C24	1.389 (3)
N2—C5	1.343 (4)	C20—C21	1.379 (4)
N3—C31	1.373 (3)	C20—H20	0.9300
N4—C35	1.336 (4)	C21—C22	1.378 (4)
N4—C31	1.342 (3)	C21—H21	0.9300
C1—C2	1.391 (3)	C22—C23	1.374 (4)
C2—C3	1.369 (4)	C22—H22	0.9300
C2—H2	0.9300	C23—C24	1.386 (4)
C3—C4	1.370 (4)	C23—H23	0.9300
C3—H3	0.9300	C24—H24	0.9300
C4—C5	1.372 (4)	C25—C26	1.379 (4)
C4—H4	0.9300	C25—C30	1.387 (4)
C5—H5	0.9300	C26—C27	1.386 (4)
C6—H6A	0.9700	C26—H26	0.9300
C6—H6B	0.9700	C27—C28	1.376 (5)
C7—C12	1.382 (4)	C27—H27	0.9300
C7—C8	1.395 (4)	C28—C29	1.365 (5)
C8—C9	1.388 (6)	C28—H28	0.9300
C8—H8	0.9300	C29—C30	1.386 (4)
C9—C10	1.359 (7)	C29—H29	0.9300
C9—H9	0.9300	C30—H30	0.9300
C10—C11	1.354 (7)	C31—C32	1.399 (4)
C10—H10	0.9300	C32—C33	1.359 (4)
C11—C12	1.382 (5)	C32—H32	0.9300
C11—H11	0.9300	C33—C34	1.375 (5)
C12—H12	0.9300	C33—H33	0.9300
C13—C14	1.379 (4)	C34—C35	1.364 (5)
C13—C18	1.389 (4)	C34—H34	0.9300
C14—C15	1.396 (4)	C35—H35	0.9300

N1—P1—C7	102.86 (11)	C14—C15—H15	119.9
N1—P1—C13	105.55 (12)	C17—C16—C15	119.6 (3)
C7—P1—C13	101.82 (13)	C17—C16—H16	120.2
N3—P2—C19	104.52 (11)	C15—C16—H16	120.2
N3—P2—C25	114.34 (12)	C16—C17—C18	120.7 (4)
C19—P2—C25	106.98 (11)	C16—C17—H17	119.6
N3—P2—C6	116.32 (12)	C18—C17—H17	119.6
C19—P2—C6	107.81 (11)	C17—C18—C13	121.0 (4)
C25—P2—C6	106.35 (12)	C17—C18—H18	119.5
C1—N1—C6	117.21 (19)	C13—C18—H18	119.5
C1—N1—P1	116.91 (15)	C20—C19—C24	119.5 (2)
C6—N1—P1	124.78 (16)	C20—C19—P2	121.79 (19)
C1—N2—C5	117.0 (2)	C24—C19—P2	118.66 (19)
C31—N3—P2	120.27 (18)	C21—C20—C19	120.5 (3)
C35—N4—C31	117.1 (3)	C21—C20—H20	119.8
N2—C1—C2	122.6 (2)	C19—C20—H20	119.8
N2—C1—N1	116.8 (2)	C22—C21—C20	119.6 (3)
C2—C1—N1	120.6 (2)	C22—C21—H21	120.2
C3—C2—C1	119.0 (3)	C20—C21—H21	120.2
C3—C2—H2	120.5	C23—C22—C21	120.6 (3)
C1—C2—H2	120.5	C23—C22—H22	119.7
C2—C3—C4	119.3 (3)	C21—C22—H22	119.7
C2—C3—H3	120.4	C22—C23—C24	120.2 (3)
C4—C3—H3	120.4	C22—C23—H23	119.9
C3—C4—C5	117.9 (3)	C24—C23—H23	119.9
C3—C4—H4	121.1	C23—C24—C19	119.6 (3)
C5—C4—H4	121.1	C23—C24—H24	120.2
N2—C5—C4	124.2 (3)	C19—C24—H24	120.2
N2—C5—H5	117.9	C26—C25—C30	119.7 (2)
C4—C5—H5	117.9	C26—C25—P2	123.20 (19)
N1—C6—P2	114.09 (16)	C30—C25—P2	117.1 (2)
N1—C6—H6A	108.7	C25—C26—C27	119.7 (3)
P2—C6—H6A	108.7	C25—C26—H26	120.2
N1—C6—H6B	108.7	C27—C26—H26	120.2
P2—C6—H6B	108.7	C28—C27—C26	120.5 (3)
H6A—C6—H6B	107.6	C28—C27—H27	119.8
C12—C7—C8	117.8 (3)	C26—C27—H27	119.8
C12—C7—P1	125.7 (2)	C29—C28—C27	119.9 (3)
C8—C7—P1	116.5 (3)	C29—C28—H28	120.0
C9—C8—C7	120.2 (4)	C27—C28—H28	120.0
C9—C8—H8	119.9	C28—C29—C30	120.4 (3)
C7—C8—H8	119.9	C28—C29—H29	119.8
C10—C9—C8	120.6 (5)	C30—C29—H29	119.8
C10—C9—H9	119.7	C29—C30—C25	119.8 (3)
C8—C9—H9	119.7	C29—C30—H30	120.1
C11—C10—C9	119.8 (4)	C25—C30—H30	120.1
C11—C10—H10	120.1	N4—C31—N3	119.9 (2)
C9—C10—H10	120.1	N4—C31—C32	121.1 (2)
C10—C11—C12	120.9 (5)	N3—C31—C32	119.0 (2)
C10—C11—H11	119.6	C33—C32—C31	120.0 (3)
C12—C11—H11	119.6	C33—C32—H32	120.0
C11—C12—C7	120.7 (4)	C31—C32—H32	120.0
C11—C12—H12	119.7	C32—C33—C34	119.2 (3)
C7—C12—H12	119.7	C32—C33—H33	120.4
C14—C13—C18	117.5 (3)	C34—C33—H33	120.4
C14—C13—P1	125.9 (2)	C35—C34—C33	117.8 (3)
C18—C13—P1	116.2 (2)	C35—C34—H34	121.1
C13—C14—C15	120.9 (3)	C33—C34—H34	121.1
C13—C14—H14	119.5	N4—C35—C34	124.8 (3)
C15—C14—H14	119.5	N4—C35—H35	117.6
C16—C15—C14	120.3 (4)	C34—C35—H35	117.6
C16—C15—H15	119.9

C7—P1—N1—C1	143.92 (19)	C14—C15—C16—C17	0.3 (6)
C13—P1—N1—C1	−109.72 (19)	C15—C16—C17—C18	0.0 (6)
C7—P1—N1—C6	−48.4 (2)	C16—C17—C18—C13	−0.2 (6)
C13—P1—N1—C6	58.0 (2)	C14—C13—C18—C17	0.0 (5)
C19—P2—N3—C31	175.99 (19)	P1—C13—C18—C17	−173.4 (3)
C25—P2—N3—C31	59.4 (2)	N3—P2—C19—C20	−148.8 (2)
C6—P2—N3—C31	−65.3 (2)	C25—P2—C19—C20	−27.2 (2)
C5—N2—C1—C2	1.7 (4)	C6—P2—C19—C20	86.8 (2)
C5—N2—C1—N1	−179.9 (2)	N3—P2—C19—C24	32.5 (2)
C6—N1—C1—N2	−31.0 (3)	C25—P2—C19—C24	154.1 (2)
P1—N1—C1—N2	137.68 (19)	C6—P2—C19—C24	−91.9 (2)
C6—N1—C1—C2	147.4 (2)	C24—C19—C20—C21	0.4 (4)
P1—N1—C1—C2	−43.9 (3)	P2—C19—C20—C21	−178.3 (2)
N2—C1—C2—C3	−1.3 (4)	C19—C20—C21—C22	−0.5 (4)
N1—C1—C2—C3	−179.6 (2)	C20—C21—C22—C23	0.4 (5)
C1—C2—C3—C4	0.2 (4)	C21—C22—C23—C24	−0.2 (5)
C2—C3—C4—C5	0.5 (5)	C22—C23—C24—C19	0.1 (4)
C1—N2—C5—C4	−1.0 (5)	C20—C19—C24—C23	−0.2 (4)
C3—C4—C5—N2	−0.1 (5)	P2—C19—C24—C23	178.5 (2)
C1—N1—C6—P2	−75.7 (3)	N3—P2—C25—C26	−157.5 (2)
P1—N1—C6—P2	116.67 (18)	C19—P2—C25—C26	87.3 (2)
N3—P2—C6—N1	−97.21 (19)	C6—P2—C25—C26	−27.7 (2)
C19—P2—C6—N1	19.7 (2)	N3—P2—C25—C30	23.1 (2)
C25—P2—C6—N1	134.16 (18)	C19—P2—C25—C30	−92.1 (2)
N1—P1—C7—C12	79.6 (3)	C6—P2—C25—C30	152.9 (2)
C13—P1—C7—C12	−29.6 (3)	C30—C25—C26—C27	−0.6 (4)
N1—P1—C7—C8	−99.3 (2)	P2—C25—C26—C27	−179.9 (2)
C13—P1—C7—C8	151.5 (2)	C25—C26—C27—C28	2.1 (4)
C12—C7—C8—C9	−1.3 (5)	C26—C27—C28—C29	−2.0 (5)
P1—C7—C8—C9	177.7 (3)	C27—C28—C29—C30	0.4 (5)
C7—C8—C9—C10	0.8 (6)	C28—C29—C30—C25	1.2 (5)
C8—C9—C10—C11	0.1 (7)	C26—C25—C30—C29	−1.0 (4)
C9—C10—C11—C12	−0.5 (6)	P2—C25—C30—C29	178.3 (2)
C10—C11—C12—C7	−0.1 (5)	C35—N4—C31—N3	−176.9 (3)
C8—C7—C12—C11	1.0 (4)	C35—N4—C31—C32	2.4 (5)
P1—C7—C12—C11	−177.9 (2)	P2—N3—C31—N4	6.4 (3)
N1—P1—C13—C14	7.1 (3)	P2—N3—C31—C32	−172.9 (2)
C7—P1—C13—C14	114.2 (3)	N4—C31—C32—C33	−1.4 (5)
N1—P1—C13—C18	179.8 (2)	N3—C31—C32—C33	177.8 (3)
C7—P1—C13—C18	−73.1 (3)	C31—C32—C33—C34	−0.5 (6)
C18—C13—C14—C15	0.4 (5)	C32—C33—C34—C35	1.4 (7)
P1—C13—C14—C15	173.0 (2)	C31—N4—C35—C34	−1.5 (6)
C13—C14—C15—C16	−0.5 (5)	C33—C34—C35—N4	−0.4 (7)

Hydrogen-bond geometry (Å, º) top

Cg is the centroids of C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···N2ⁱ	0.93	2.71	3.577 (3)	155
C21—H21···N3ⁱⁱ	0.93	2.73	3.569 (4)	150
C28—H28···Cgⁱⁱⁱ	0.93	2.87	3.603 (3)	136

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x, y−1, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₅H₃₀N₄P₂
M_r	568.57
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	22.505 (7), 9.142 (3), 29.606 (9)
β (°)	102.877 (5)
V (Å³)	5938 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.753, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16500, 6035, 4510
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.126, 1.15
No. of reflections	6035
No. of parameters	370
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.28

Computer programs: APEX2 (Bruker, 2007), APEX2 and SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).