N,N-Bis(diphenyl-phosphan-yl)cyclo--penta-namine.

The coordination around the N atom in the title compound, C(29)H(29)NP(2), shows an almost planar geometry, defined by the attached P and C atoms, in order to accomodate the steric bulk of the phenyl rings. The distortion of the trigonal-pyramidal geometry of the N atom is illustrated by the bond angles ranging between 115.22 (12) and 121.76 (9)°. The P atoms present a pyramidal environment with bond angles ranging from 100.62 (9) to 104.71 (8)°. One of the C atoms in the cyclo-pentyl ring displays a 0.822 (4):0.178 (4) positional disorder. Within the crystal structure, intra-molecular C-H⋯P hydrogen bonds together with inter- and intra-molecular C-H⋯π inter-actions link the mol-ecules into a supra-molecular two-dimensional network.

Related literature

For similar structures, see: Keat et al. (1981 ▶); Cotton et al. (1996 ▶); Fei et al. (2003 ▶); Cloete et al. (2008 ▶, 2009 ▶, 2010 ▶); Engelbrecht et al. (2010 ▶).

Experimental

Crystal data

C29H29NP2

M = 453.47

Triclinic,

a = 8.803 (5) Å

b = 11.166 (4) Å

c = 12.685 (5) Å

α = 97.144 (4)°

β = 101.261 (5)°

γ = 99.707 (5)°

V = 1189.3 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.2 mm−1

T = 100 K

0.19 × 0.13 × 0.08 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.963, T max = 0.983

12794 measured reflections

5817 independent reflections

4333 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.106

S = 1.06

5817 reflections

293 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048907/bg2375sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048907/bg2375Isup2.hkl

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

C29H29NP2	Z = 2
Mr = 453.47	F(000) = 480
Triclinic, P1	Dx = 1.266 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.803 (5) Å	Cell parameters from 2872 reflections
b = 11.166 (4) Å	θ = 2.7–28.0°
c = 12.685 (5) Å	µ = 0.2 mm−1
α = 97.144 (4)°	T = 100 K
β = 101.261 (5)°	Cuboid, white
γ = 99.707 (5)°	0.19 × 0.13 × 0.08 mm
V = 1189.3 (10) Å3

Bruker X8 APEXII 4K Kappa CCD diffractometer	5817 independent reflections
Radiation source: fine-focus sealed tube	4333 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω and φ scans	θmax = 28.3°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.963, Tmax = 0.983	k = −14→14
12794 measured reflections	l = −16→16

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0343P)2 + 0.5079P] where P = (Fo2 + 2Fc2)/3
5817 reflections	(Δ/σ)max = 0.015
293 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Experimental. The intensity data were collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 60 s/frame. A total of 1148 frames were collected with a frame width of 0.5° covering up to θ = 28.27° with 98.7% completeness accomplished. Spectroscopy data: 1H NMR (300 MHz, CD2Cl2): δ = 1.3 to 1.9 (m, 8H, 4 x CH2), 3.8 (m, 1H, CH), 7.3 to 7.4 (m, 20H, Ar); 31P NMR (121 MHz, CD2Cl2): δ = 50.6 (s).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
C1	0.91678 (19)	0.34252 (17)	0.75151 (15)	0.0160 (4)
H1	0.9698	0.278	0.7211	0.019*
C2	0.9126 (2)	0.44037 (18)	0.67528 (16)	0.0198 (4)
H2A	0.9168	0.4043	0.6008	0.024*
H2B	0.8154	0.4746	0.6716	0.024*
C3A	1.0595 (2)	0.5401 (2)	0.72654 (18)	0.0283 (5)	0.822 (4)
H3A1	1.0467	0.6203	0.7042	0.034*	0.822 (4)
H3A2	1.1549	0.5173	0.706	0.034*	0.822 (4)
C4A	1.0695 (3)	0.5448 (2)	0.8501 (2)	0.0252 (6)	0.822 (4)
H4A1	1.1775	0.5823	0.8926	0.03*	0.822 (4)
H4A2	0.9939	0.5922	0.8748	0.03*	0.822 (4)
C5A	1.0262 (2)	0.41072 (18)	0.86124 (16)	0.0222 (4)	0.822 (4)
H5A1	0.9707	0.4024	0.9215	0.027*	0.822 (4)
H5A2	1.1226	0.3755	0.8771	0.027*	0.822 (4)
C3B	1.0595 (2)	0.5401 (2)	0.72654 (18)	0.0283 (5)	0.178 (4)
H3B1	1.1228	0.5556	0.6714	0.034*	0.178 (4)
H3B2	1.0268	0.6177	0.7509	0.034*	0.178 (4)
C4B	1.1460 (13)	0.5064 (11)	0.8099 (10)	0.0252 (6)	0.178 (4)
H4B1	1.1998	0.5793	0.8655	0.03*	0.178 (4)
H4B2	1.2274	0.4649	0.7861	0.03*	0.178 (4)
C5B	1.0262 (2)	0.41072 (18)	0.86124 (16)	0.0222 (4)	0.178 (4)
H5B1	1.0822	0.3549	0.9018	0.027*	0.178 (4)
H5B2	0.9686	0.4545	0.9082	0.027*	0.178 (4)
C11	0.7060 (2)	0.13812 (17)	0.55819 (15)	0.0155 (4)
C12	0.6196 (2)	0.20991 (19)	0.49657 (16)	0.0222 (4)
H12	0.5488	0.2514	0.5273	0.027*
C13	0.6355 (2)	0.22151 (19)	0.39194 (16)	0.0222 (4)
H13	0.5776	0.2722	0.3521	0.027*
C14	0.7355 (2)	0.15971 (18)	0.34479 (16)	0.0193 (4)
H14	0.7461	0.1676	0.2727	0.023*
C15	0.8197 (2)	0.08648 (19)	0.40339 (16)	0.0228 (4)
H15	0.8877	0.0431	0.3713	0.027*
C16	0.8051 (2)	0.07612 (18)	0.50916 (16)	0.0191 (4)
H16	0.8639	0.0258	0.5487	0.023*
C21	0.8152 (2)	0.03788 (17)	0.74897 (15)	0.0164 (4)
C22	0.7770 (2)	−0.08818 (18)	0.70735 (16)	0.0199 (4)
H22	0.688	−0.1188	0.6487	0.024*
C23	0.8659 (2)	−0.16896 (18)	0.74967 (16)	0.0218 (4)
H23	0.8371	−0.2543	0.7205	0.026*
C24	0.9970 (2)	−0.12568 (19)	0.83469 (16)	0.0227 (4)
H24	1.058	−0.1811	0.8642	0.027*
C25	1.0383 (2)	−0.00127 (19)	0.87619 (17)	0.0239 (4)
H25	1.1293	0.029	0.9334	0.029*
C26	0.9474 (2)	0.08001 (18)	0.83467 (16)	0.0206 (4)
H26	0.9757	0.165	0.865	0.025*
C31	0.4685 (2)	0.35868 (17)	0.71326 (15)	0.0157 (4)
C32	0.4624 (2)	0.45295 (19)	0.65030 (16)	0.0204 (4)
H32	0.5452	0.5236	0.6677	0.024*
C33	0.3364 (2)	0.4442 (2)	0.56256 (17)	0.0253 (5)
H33	0.3344	0.5081	0.5197	0.03*
C34	0.2143 (2)	0.3431 (2)	0.53752 (16)	0.0246 (5)
H34	0.1288	0.337	0.4771	0.03*
C35	0.2165 (2)	0.24971 (19)	0.60091 (16)	0.0227 (4)
H35	0.1317	0.1805	0.5843	0.027*
C36	0.3429 (2)	0.25774 (18)	0.68856 (16)	0.0191 (4)
H36	0.3436	0.1941	0.7318	0.023*
C41	0.5704 (2)	0.29021 (17)	0.91837 (15)	0.0163 (4)
C42	0.4502 (2)	0.33272 (19)	0.96094 (16)	0.0207 (4)
H42	0.4064	0.3973	0.9326	0.025*
C43	0.3941 (2)	0.2821 (2)	1.04375 (17)	0.0257 (5)
H43	0.312	0.3116	1.0713	0.031*
C44	0.4581 (2)	0.1883 (2)	1.08629 (16)	0.0246 (4)
H44	0.4195	0.1529	1.1427	0.03*
C45	0.5785 (2)	0.14650 (19)	1.04613 (16)	0.0220 (4)
H45	0.6231	0.0828	1.0756	0.026*
C46	0.6347 (2)	0.19717 (18)	0.96279 (15)	0.0184 (4)
H46	0.7175	0.168	0.9361	0.022*
N1	0.75799 (16)	0.27932 (14)	0.76314 (12)	0.0155 (3)
P1	0.67417 (5)	0.13242 (5)	0.69726 (4)	0.01549 (12)
P2	0.64933 (5)	0.37383 (5)	0.81951 (4)	0.01544 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0132 (8)	0.0182 (10)	0.0159 (10)	0.0018 (7)	0.0040 (7)	0.0010 (8)
C2	0.0180 (8)	0.0241 (11)	0.0195 (10)	0.0056 (8)	0.0058 (8)	0.0071 (8)
C3A	0.0296 (11)	0.0227 (12)	0.0311 (13)	−0.0010 (9)	0.0105 (9)	0.0010 (10)
C4A	0.0254 (12)	0.0214 (14)	0.0251 (14)	−0.0007 (10)	0.0044 (10)	−0.0016 (11)
C5A	0.0175 (9)	0.0259 (12)	0.0199 (11)	0.0022 (8)	0.0009 (8)	−0.0006 (9)
C3B	0.0296 (11)	0.0227 (12)	0.0311 (13)	−0.0010 (9)	0.0105 (9)	0.0010 (10)
C4B	0.0254 (12)	0.0214 (14)	0.0251 (14)	−0.0007 (10)	0.0044 (10)	−0.0016 (11)
C5B	0.0175 (9)	0.0259 (12)	0.0199 (11)	0.0022 (8)	0.0009 (8)	−0.0006 (9)
C11	0.0151 (8)	0.0143 (9)	0.0138 (9)	−0.0017 (7)	0.0014 (7)	−0.0009 (7)
C12	0.0241 (9)	0.0267 (12)	0.0176 (11)	0.0114 (8)	0.0041 (8)	0.0019 (9)
C13	0.0274 (10)	0.0220 (11)	0.0167 (10)	0.0080 (8)	0.0000 (8)	0.0045 (8)
C14	0.0207 (9)	0.0220 (11)	0.0127 (10)	−0.0017 (8)	0.0026 (7)	0.0034 (8)
C15	0.0233 (9)	0.0285 (12)	0.0206 (11)	0.0085 (9)	0.0095 (8)	0.0067 (9)
C16	0.0193 (9)	0.0230 (11)	0.0166 (10)	0.0066 (8)	0.0042 (8)	0.0058 (8)
C21	0.0194 (8)	0.0189 (10)	0.0141 (10)	0.0055 (8)	0.0078 (7)	0.0055 (8)
C22	0.0227 (9)	0.0192 (10)	0.0173 (10)	0.0018 (8)	0.0060 (8)	0.0022 (8)
C23	0.0304 (10)	0.0160 (10)	0.0224 (11)	0.0056 (8)	0.0124 (9)	0.0036 (8)
C24	0.0295 (10)	0.0242 (11)	0.0202 (11)	0.0129 (9)	0.0101 (9)	0.0082 (9)
C25	0.0279 (10)	0.0267 (12)	0.0170 (10)	0.0101 (9)	0.0011 (8)	0.0024 (9)
C26	0.0274 (10)	0.0179 (10)	0.0169 (10)	0.0068 (8)	0.0043 (8)	0.0017 (8)
C31	0.0157 (8)	0.0190 (10)	0.0141 (9)	0.0065 (7)	0.0051 (7)	0.0016 (8)
C32	0.0181 (9)	0.0226 (11)	0.0224 (11)	0.0051 (8)	0.0074 (8)	0.0049 (9)
C33	0.0265 (10)	0.0344 (13)	0.0210 (11)	0.0153 (9)	0.0079 (9)	0.0103 (9)
C34	0.0226 (9)	0.0375 (13)	0.0143 (10)	0.0151 (9)	0.0010 (8)	−0.0008 (9)
C35	0.0185 (9)	0.0248 (11)	0.0214 (11)	0.0041 (8)	0.0009 (8)	−0.0039 (9)
C36	0.0199 (9)	0.0191 (10)	0.0188 (10)	0.0049 (8)	0.0053 (8)	0.0017 (8)
C41	0.0150 (8)	0.0184 (10)	0.0131 (9)	0.0008 (7)	0.0018 (7)	−0.0005 (8)
C42	0.0193 (9)	0.0260 (11)	0.0183 (10)	0.0073 (8)	0.0053 (8)	0.0041 (9)
C43	0.0213 (9)	0.0368 (13)	0.0204 (11)	0.0066 (9)	0.0085 (8)	0.0026 (9)
C44	0.0259 (10)	0.0309 (12)	0.0150 (10)	−0.0019 (9)	0.0065 (8)	0.0032 (9)
C45	0.0274 (10)	0.0204 (11)	0.0155 (10)	0.0024 (8)	0.0008 (8)	0.0024 (8)
C46	0.0189 (9)	0.0198 (10)	0.0146 (10)	0.0027 (8)	0.0024 (7)	−0.0007 (8)
N1	0.0127 (7)	0.0162 (8)	0.0166 (8)	0.0007 (6)	0.0042 (6)	−0.0002 (7)
P1	0.0157 (2)	0.0163 (3)	0.0142 (3)	0.00285 (19)	0.00334 (18)	0.0017 (2)
P2	0.0146 (2)	0.0171 (3)	0.0149 (3)	0.00371 (19)	0.00380 (18)	0.0017 (2)

C1—N1	1.499 (2)	C23—C24	1.388 (3)
C1—C2	1.547 (3)	C23—H23	0.95
C1—C5A	1.553 (3)	C24—C25	1.383 (3)
C1—H1	1	C24—H24	0.95
C2—C3A	1.530 (3)	C25—C26	1.393 (3)
C2—H2A	0.99	C25—H25	0.95
C2—H2B	0.99	C26—H26	0.95
C3A—C4A	1.546 (3)	C31—C36	1.396 (3)
C3A—H3A1	0.99	C31—C32	1.400 (3)
C3A—H3A2	0.99	C31—P2	1.842 (2)
C4A—C5A	1.512 (3)	C32—C33	1.390 (3)
C4A—H4A1	0.99	C32—H32	0.95
C4A—H4A2	0.99	C33—C34	1.378 (3)
C5A—H5A1	0.99	C33—H33	0.95
C5A—H5A2	0.99	C34—C35	1.394 (3)
C4B—H4B1	0.99	C34—H34	0.95
C4B—H4B2	0.99	C35—C36	1.393 (3)
C11—C16	1.392 (2)	C35—H35	0.95
C11—C12	1.400 (3)	C36—H36	0.95
C11—P1	1.847 (2)	C41—C46	1.391 (3)
C12—C13	1.381 (3)	C41—C42	1.403 (2)
C12—H12	0.95	C41—P2	1.8274 (19)
C13—C14	1.384 (3)	C42—C43	1.387 (3)
C13—H13	0.95	C42—H42	0.95
C14—C15	1.382 (3)	C43—C44	1.388 (3)
C14—H14	0.95	C43—H43	0.95
C15—C16	1.389 (3)	C44—C45	1.386 (3)
C15—H15	0.95	C44—H44	0.95
C16—H16	0.95	C45—C46	1.393 (3)
C21—C26	1.397 (3)	C45—H45	0.95
C21—C22	1.400 (3)	C46—H46	0.95
C21—P1	1.8388 (19)	N1—P1	1.7157 (17)
C22—C23	1.381 (3)	N1—P2	1.7205 (16)
C22—H22	0.95
N1—C1—C2	114.93 (14)	C22—C23—H23	120
N1—C1—C5A	113.39 (15)	C24—C23—H23	120
C2—C1—C5A	105.15 (16)	C25—C24—C23	119.51 (18)
N1—C1—H1	107.7	C25—C24—H24	120.2
C2—C1—H1	107.7	C23—C24—H24	120.2
C5A—C1—H1	107.7	C24—C25—C26	120.43 (19)
C3A—C2—C1	104.78 (16)	C24—C25—H25	119.8
C3A—C2—H2A	110.8	C26—C25—H25	119.8
C1—C2—H2A	110.8	C25—C26—C21	120.72 (19)
C3A—C2—H2B	110.8	C25—C26—H26	119.6
C1—C2—H2B	110.8	C21—C26—H26	119.6
H2A—C2—H2B	108.9	C36—C31—C32	118.66 (17)
C2—C3A—C4A	103.07 (17)	C36—C31—P2	124.46 (14)
C2—C3A—H3A1	111.1	C32—C31—P2	116.80 (14)
C4A—C3A—H3A1	111.1	C33—C32—C31	120.67 (19)
C2—C3A—H3A2	111.1	C33—C32—H32	119.7
C4A—C3A—H3A2	111.1	C31—C32—H32	119.7
H3A1—C3A—H3A2	109.1	C34—C33—C32	120.24 (19)
C5A—C4A—C3A	103.38 (19)	C34—C33—H33	119.9
C5A—C4A—H4A1	111.1	C32—C33—H33	119.9
C3A—C4A—H4A1	111.1	C33—C34—C35	119.90 (18)
C5A—C4A—H4A2	111.1	C33—C34—H34	120.1
C3A—C4A—H4A2	111.1	C35—C34—H34	120
H4A1—C4A—H4A2	109.1	C36—C35—C34	120.09 (19)
C4A—C5A—C1	107.22 (17)	C36—C35—H35	120
C4A—C5A—H5A1	110.3	C34—C35—H35	120
C1—C5A—H5A1	110.3	C35—C36—C31	120.40 (18)
C4A—C5A—H5A2	110.3	C35—C36—H36	119.8
C1—C5A—H5A2	110.3	C31—C36—H36	119.8
H5A1—C5A—H5A2	108.5	C46—C41—C42	118.29 (17)
H4B1—C4B—H4B2	108.5	C46—C41—P2	123.86 (13)
C16—C11—C12	117.63 (17)	C42—C41—P2	117.40 (14)
C16—C11—P1	125.95 (14)	C43—C42—C41	121.13 (18)
C12—C11—P1	116.41 (13)	C43—C42—H42	119.4
C13—C12—C11	121.19 (17)	C41—C42—H42	119.4
C13—C12—H12	119.4	C42—C43—C44	119.87 (18)
C11—C12—H12	119.4	C42—C43—H43	120.1
C12—C13—C14	120.32 (18)	C44—C43—H43	120.1
C12—C13—H13	119.8	C45—C44—C43	119.67 (18)
C14—C13—H13	119.8	C45—C44—H44	120.2
C15—C14—C13	119.47 (18)	C43—C44—H44	120.2
C15—C14—H14	120.3	C44—C45—C46	120.47 (18)
C13—C14—H14	120.3	C44—C45—H45	119.8
C14—C15—C16	120.17 (17)	C46—C45—H45	119.8
C14—C15—H15	119.9	C41—C46—C45	120.55 (17)
C16—C15—H15	119.9	C41—C46—H46	119.7
C15—C16—C11	121.20 (17)	C45—C46—H46	119.7
C15—C16—H16	119.4	C1—N1—P1	121.43 (12)
C11—C16—H16	119.4	C1—N1—P2	115.22 (12)
C26—C21—C22	117.78 (17)	P1—N1—P2	121.76 (9)
C26—C21—P1	124.69 (15)	N1—P1—C21	104.70 (9)
C22—C21—P1	117.13 (14)	N1—P1—C11	102.52 (8)
C23—C22—C21	121.44 (19)	C21—P1—C11	101.65 (8)
C23—C22—H22	119.3	N1—P2—C41	104.71 (8)
C21—C22—H22	119.3	N1—P2—C31	104.59 (8)
C22—C23—C24	120.10 (19)	C41—P2—C31	100.62 (9)
N1—C1—C2—C3A	145.49 (16)	C42—C43—C44—C45	0.5 (3)
C5A—C1—C2—C3A	20.08 (18)	C43—C44—C45—C46	−0.6 (3)
C1—C2—C3A—C4A	−37.2 (2)	C42—C41—C46—C45	1.1 (3)
C2—C3A—C4A—C5A	40.1 (2)	P2—C41—C46—C45	173.20 (15)
C3A—C4A—C5A—C1	−27.7 (2)	C44—C45—C46—C41	−0.2 (3)
N1—C1—C5A—C4A	−121.37 (17)	C2—C1—N1—P1	103.43 (17)
C2—C1—C5A—C4A	4.99 (19)	C5A—C1—N1—P1	−135.56 (14)
C16—C11—C12—C13	−1.8 (3)	C2—C1—N1—P2	−62.41 (19)
P1—C11—C12—C13	179.38 (16)	C5A—C1—N1—P2	58.59 (18)
C11—C12—C13—C14	1.4 (3)	C1—N1—P1—C21	59.96 (15)
C12—C13—C14—C15	−0.2 (3)	P2—N1—P1—C21	−135.12 (10)
C13—C14—C15—C16	−0.7 (3)	C1—N1—P1—C11	−45.82 (15)
C14—C15—C16—C11	0.3 (3)	P2—N1—P1—C11	119.10 (10)
C12—C11—C16—C15	0.9 (3)	C26—C21—P1—N1	8.13 (17)
P1—C11—C16—C15	179.66 (15)	C22—C21—P1—N1	−179.28 (13)
C26—C21—C22—C23	0.5 (3)	C26—C21—P1—C11	114.56 (16)
P1—C21—C22—C23	−172.64 (14)	C22—C21—P1—C11	−72.86 (15)
C21—C22—C23—C24	−0.6 (3)	C16—C11—P1—N1	112.33 (17)
C22—C23—C24—C25	−0.3 (3)	C12—C11—P1—N1	−68.92 (16)
C23—C24—C25—C26	1.3 (3)	C16—C11—P1—C21	4.20 (19)
C24—C25—C26—C21	−1.4 (3)	C12—C11—P1—C21	−177.05 (15)
C22—C21—C26—C25	0.5 (3)	C1—N1—P2—C41	−135.34 (13)
P1—C21—C26—C25	173.05 (14)	P1—N1—P2—C41	58.87 (12)
C36—C31—C32—C33	−2.2 (3)	C1—N1—P2—C31	119.28 (13)
P2—C31—C32—C33	174.66 (14)	P1—N1—P2—C31	−46.52 (12)
C31—C32—C33—C34	1.0 (3)	C46—C41—P2—N1	20.87 (18)
C32—C33—C34—C35	0.5 (3)	C42—C41—P2—N1	−166.95 (15)
C33—C34—C35—C36	−0.9 (3)	C46—C41—P2—C31	129.18 (17)
C34—C35—C36—C31	−0.4 (3)	C42—C41—P2—C31	−58.64 (17)
C32—C31—C36—C35	1.9 (3)	C36—C31—P2—N1	76.55 (16)
P2—C31—C36—C35	−174.75 (14)	C32—C31—P2—N1	−100.16 (15)
C46—C41—C42—C43	−1.2 (3)	C36—C31—P2—C41	−31.86 (17)
P2—C41—C42—C43	−173.85 (16)	C32—C31—P2—C41	151.43 (14)
C41—C42—C43—C44	0.5 (3)

Cg1 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···P2	0.99	2.82	3.269 (2)	108
C5A—H5A1···P2	0.99	2.82	3.202 (3)	104
C12—H12···Cg1	0.95	2.72	3.667 (2)	174
C3A—H3A2···Cg1i	0.99	2.89	3.811 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯P2	0.99	2.82	3.269 (2)	108
C5A—H5A1⋯P2	0.99	2.82	3.202 (3)	104
C12—H12⋯Cg1	0.95	2.72	3.667 (2)	174
C3A—H3A2⋯Cg1i	0.99	2.89	3.811 (2)	155

Symmetry code: (i) .