Hydrogen bis­(tetra­phenyl­imido­diphospinic acid) triiodide

In the crystal structure of the title compound, [(C₂₄H₂₁NO₂P₂)₂H]⁺·I₃⁻, the triiodide anion is linear, sitting across a centre of symmetry, with I—I distances of 2.9130 (6) Å. The [H{(OPPh₂)₂NH}₂]⁺ cation is formed by two symmetry-related mol­ecules of tetra­phenyl­imido­diphos­phinic acid, (OPPh₂)₂NH, exbiting for the O—P—N—P—O skeleton an anti conformation [code (−,+)/(+,−)] with an angular P—N—P fragment. The charge is determined by a single proton shared by these two molecules, disordered across a centre of symmetry and forming an O—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.053
• wR factor = 0.120
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.33
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C48 H43 I3 N2 O4 P4
            Atom count from _chemical_formula_moiety:C48 H43 I1 N2 O4 P4
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
   6 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

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

---

S1. Comment

The tetraphenylimidodiphosphinato ligand [(OPPh₂)₂N]^- is extensively used in coordination chemistry due to its ability to form stable complexes with a variety of main group and transition metals, Garcia-Montalvo et al., 2001; Ghesner et al., 2005; Haiduc, 2004; Silvestru et al., 2001; Silvestru & Drake, 2001; Yi et al., 2006. In metal complexes the O,O'-monometallic biconnective pattern of this ligand is the most common, with an angular P—N—P fragment (Silvestru & Drake, 2001). Due to its ideal framework structure for minimization of radiationless decay pathways of NIR f-f luminescence, [(OPPh₂)₂N]^- is also an efficient sensitizer for NIR light emitting complexes of Nd^III, Er^III and Yb^III (Bassett et al., 2005).

Metal complexes with the neutral ligand (OPPh₂)₂NH are much less common (Rietzel et al., 1990). The crystal structure of tetraphenylimidodiphosphinic acid, (OPPh₂)₂NH is known (Noth, 1982) and it features a polymeric structure with P—N—P fragments connected by symmetric O—H—O bridges.

The crystal of the title compound contains a perfect linear triiodide anion and the cation [H{(OPPh₂)₂NH}₂]⁺ (Figure 1). In this cation a hydrogen atom (H1A) bridges two symmetry related (OPPh₂)₂NH molecules at O1. H1A appears to be disorded over two positions. A similar disordered hydrogen has been already reported in a similar compound [(Me₃PO)₂H][AuI₂] (Godfrey et al., 1996). This proton briges two (OPPh₂)₂NH molecules at O1and its symmetry equivalent O1ⁱ atom [O1···O1ⁱ = 2.411 (5) Å; symmetry code: (i) = -x, -y + 2, -z + 1].

The P—O and N—P distances are of the same magnitude [O1—P1 = 1.516 (3) Å, O2—P2 1.493 (4) Å; N1—P1 = 1.641 (4) Å, N1—P2 = 1.669 (4) Å] suggesting a delocalization of the positive charge over the OPNPO skeleton of both (OPPh₂)₂NH molecules (Silvestru & Drake, 2001b).

Strong intermolecular interactions between the NH groups and the unprotonated oxygen atom, O2, from symmetry related cation units [H1···O2ⁱⁱ = 1.90 Å; N1···O2ⁱⁱ = 2.726 (5) Å; N1—H1—O2ⁱⁱ = 161°; symmetry code: (ii) = -x + 1, -y + 2, -z + 1] result in a chain polymer association (Figure 2). The hydrogen-bonding pattern can be designated as R₂²(8) (Bernstein et al., 1995).

Related literature

For related literature, see: Bassett et al. (2005); Bernstein et al. (1995); Garcia-Montalvo et al. (2001); Ghesner et al. (2005); Godfrey et al. (1996); Haiduc (2004); Noth (1982); Rietzel et al. (1990); Silvestru et al. (2001); Silvestru & Drake (2001); Yi et al. (2006).

.

S2. Experimental

The compound was obtained from the reaction of elemental Se, I₂ and (SePPh₂)₂NH (1:1:1 molar ratio) in dichloromethane. The crystals (33% yield) were obtained by slow diffusion from CH₂Cl₂/hexane. Spectroscopic analysis: ¹H NMR (CDCl₃, 300 MHz): δ 7.34 (ddd, 816H, C₆H₅-meta, ³J_HH = 7.7, ⁴J_HH = 3.4 Hz), 7.51 (7, 8H, C₆H₅-para, ³J_HH = 6.7 Hz), 7.65 (dd, 16H, C₆H₅-ortho, ³J_PH = 13.3, ³J_HH = 7.5 Hz); ¹³C NMR (CDCl₃, 75.47 MHz): 128.59 (m, C-meta), 130.50 (dd, C-ipso, ³J_PP = 130.5, ⁴J_PP = 1.7 Hz), 131.70 (m, C-ortho), 132.57 (s, C-para); ³¹P NMR (CDCl₃, 121.48 MHz): δ 25.4 (s). The same compound was obtained by using elemental Se, I₂ and (SPPh₂)₂NH (1:1:1 molar ratio).

S3. Refinement

All hydrogen atoms were placed in calculated positions using a riding model, with C—H = 0.93–0.97 Å and U_iso= 1.2U_eq (C) for aryl H. The H atom bonded to N1 was found in a difference map and refined with a restrained N—H distance of 0.86 (4) Å. The half hydrogen attached to O1 was located on a difference map and refined as a riding atom at 0.82 Å from O1.

There is a Q peak close to the O2 atom and the refinament of the structure was made taking into account this feature by partial protonation at O2 with different occupancy factors. In all our attempts the refinement did not yielded anything meaningful. The main problem is that the proton partially localized on O2 gets very close to the H1 atom bonded to nitrogen N1.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures

	Fig. 1. : A view of title compound showing the atom-numbering scheme at 30% probability thermal ellipsoids (hydrogen bonds shown as dotted lines). H atoms are shown as small spheres of arbitrary radii. Both components of the disorderd H1A are showed.
	Fig. 2. : View of the secondary interactions H···O (indicated as dotted lines). All another hydrogen atoms were omitted for clarity.

Hydrogen bis(tetraphenylimidodiphospinic acid) triiodide

Crystal data

C48H43N2O4P4^+·I3^−	Z = 1
Mr = 1216.42	F(000) = 596
Triclinic, P1	Dx = 1.633 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2291 (14) Å	Cell parameters from 3014 reflections
b = 11.3075 (15) Å	θ = 2.3–21.7°
c = 11.3840 (15) Å	µ = 2.07 mm^−1
α = 91.451 (2)°	T = 297 K
β = 96.411 (2)°	Block, brown
γ = 108.696 (2)°	0.23 × 0.17 × 0.14 mm
V = 1236.8 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	4347 independent reflections
Radiation source: fine-focus sealed tube	3662 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SHELXTL; Bruker, 2001)	h = −12→12
Tmin = 0.635, Tmax = 0.745	k = −13→13
12050 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0442P)^2 + 2.0708P] where P = (Fo^2 + 2Fc^2)/3
4347 reflections	(Δ/σ)max < 0.001
281 parameters	Δρmax = 1.45 e Å^−3
1 restraint	Δρmin = −0.63 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2542 (5)	1.2068 (5)	0.5979 (4)	0.0371 (11)
C2	0.2634 (6)	1.2393 (5)	0.4821 (5)	0.0469 (13)
H2	0.2488	1.1778	0.4218	0.056*
C3	0.2939 (7)	1.3619 (6)	0.4563 (6)	0.0638 (17)
H3	0.3014	1.3838	0.3786	0.077*
C4	0.3132 (9)	1.4524 (7)	0.5448 (8)	0.086 (2)
H4	0.3333	1.5356	0.5268	0.103*
C5	0.3034 (10)	1.4215 (7)	0.6585 (7)	0.093 (3)
H5	0.3170	1.4836	0.7180	0.111*
C6	0.2734 (7)	1.2985 (6)	0.6865 (5)	0.0606 (16)
H6	0.2661	1.2776	0.7645	0.073*
C7	0.2370 (5)	1.0310 (5)	0.7854 (4)	0.0360 (11)
C8	0.3676 (6)	1.0853 (5)	0.8477 (5)	0.0507 (14)
H8	0.4422	1.1274	0.8082	0.061*
C9	0.3871 (7)	1.0771 (6)	0.9679 (5)	0.0627 (17)
H9	0.4746	1.1156	1.0100	0.075*
C10	0.2795 (8)	1.0131 (7)	1.0264 (5)	0.0703 (19)
H10	0.2940	1.0072	1.1078	0.084*
C11	0.1503 (7)	0.9575 (6)	0.9654 (5)	0.0633 (17)
H11	0.0773	0.9130	1.0055	0.076*
C12	0.1271 (6)	0.9668 (5)	0.8445 (5)	0.0482 (13)
H12	0.0386	0.9304	0.8034	0.058*
C13	0.2745 (6)	0.7944 (5)	0.4045 (4)	0.0419 (12)
C14	0.1562 (7)	0.8115 (6)	0.3462 (5)	0.0560 (15)
H14	0.1115	0.8588	0.3836	0.067*
C15	0.1043 (8)	0.7589 (7)	0.2329 (5)	0.074 (2)
H15	0.0234	0.7685	0.1949	0.089*
C16	0.1724 (9)	0.6932 (7)	0.1774 (6)	0.085 (3)
H16	0.1382	0.6592	0.1005	0.102*
C17	0.2890 (9)	0.6760 (6)	0.2317 (7)	0.082 (2)
H17	0.3341	0.6308	0.1919	0.098*
C18	0.3418 (7)	0.7259 (5)	0.3472 (5)	0.0564 (16)
H18	0.4211	0.7133	0.3851	0.068*
C19	0.2451 (5)	0.7607 (4)	0.6548 (4)	0.0360 (11)
C20	0.1062 (6)	0.6920 (6)	0.6285 (5)	0.0531 (15)
H20	0.0582	0.6957	0.5551	0.064*
C21	0.0388 (6)	0.6177 (6)	0.7120 (6)	0.0693 (19)
H21	−0.0552	0.5718	0.6949	0.083*
C22	0.1088 (7)	0.6109 (6)	0.8195 (5)	0.0589 (16)
H22	0.0623	0.5603	0.8751	0.071*
C23	0.2466 (6)	0.6780 (5)	0.8460 (5)	0.0513 (14)
H23	0.2934	0.6735	0.9197	0.062*
C24	0.3163 (6)	0.7523 (5)	0.7642 (4)	0.0437 (12)
H24	0.4107	0.7968	0.7818	0.052*
I1	0.5000	0.5000	0.0000	0.0595 (2)
I2	0.22309 (5)	0.35171 (5)	0.04825 (5)	0.0815 (2)
N1	0.3180 (4)	0.9957 (4)	0.5632 (3)	0.0340 (9)
O2	0.4953 (4)	0.8718 (3)	0.5776 (3)	0.0482 (9)
O1	0.0584 (3)	0.9733 (3)	0.5882 (3)	0.0444 (9)
H1A	0.0427	0.9783	0.5166	0.067*	0.50
P1	0.20980 (12)	1.04556 (12)	0.63033 (11)	0.0323 (3)
P2	0.34452 (13)	0.85791 (12)	0.55250 (11)	0.0343 (3)
H1	0.370 (4)	1.051 (4)	0.523 (4)	0.038 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.036 (3)	0.037 (3)	0.041 (3)	0.016 (2)	0.006 (2)	0.005 (2)
C2	0.053 (3)	0.047 (3)	0.044 (3)	0.022 (3)	0.003 (3)	0.008 (3)
C3	0.075 (4)	0.062 (4)	0.064 (4)	0.031 (3)	0.017 (3)	0.032 (3)
C4	0.119 (7)	0.046 (4)	0.104 (6)	0.038 (4)	0.023 (5)	0.020 (4)
C5	0.162 (9)	0.050 (4)	0.076 (5)	0.046 (5)	0.024 (5)	0.001 (4)
C6	0.089 (5)	0.054 (4)	0.049 (4)	0.034 (3)	0.017 (3)	0.007 (3)
C7	0.038 (3)	0.040 (3)	0.033 (3)	0.016 (2)	0.007 (2)	0.005 (2)
C8	0.051 (3)	0.054 (3)	0.043 (3)	0.013 (3)	0.003 (3)	0.008 (3)
C9	0.073 (4)	0.070 (4)	0.040 (3)	0.023 (4)	−0.015 (3)	−0.001 (3)
C10	0.108 (6)	0.080 (5)	0.028 (3)	0.039 (4)	0.005 (4)	0.009 (3)
C11	0.083 (5)	0.073 (4)	0.048 (4)	0.035 (4)	0.033 (3)	0.023 (3)
C12	0.044 (3)	0.055 (3)	0.049 (3)	0.018 (3)	0.011 (3)	0.013 (3)
C13	0.051 (3)	0.037 (3)	0.036 (3)	0.008 (2)	0.016 (2)	0.003 (2)
C14	0.068 (4)	0.061 (4)	0.038 (3)	0.019 (3)	0.012 (3)	0.001 (3)
C15	0.083 (5)	0.081 (5)	0.043 (4)	0.004 (4)	0.005 (3)	0.002 (3)
C16	0.093 (6)	0.080 (5)	0.048 (4)	−0.022 (5)	0.024 (4)	−0.021 (4)
C17	0.093 (6)	0.052 (4)	0.082 (5)	−0.012 (4)	0.052 (5)	−0.027 (4)
C18	0.065 (4)	0.041 (3)	0.061 (4)	0.007 (3)	0.031 (3)	−0.004 (3)
C19	0.042 (3)	0.034 (3)	0.035 (3)	0.014 (2)	0.013 (2)	0.011 (2)
C20	0.045 (3)	0.062 (4)	0.051 (3)	0.014 (3)	0.004 (3)	0.024 (3)
C21	0.046 (4)	0.076 (5)	0.076 (5)	0.001 (3)	0.017 (3)	0.034 (4)
C22	0.065 (4)	0.060 (4)	0.053 (4)	0.013 (3)	0.026 (3)	0.031 (3)
C23	0.065 (4)	0.057 (4)	0.036 (3)	0.024 (3)	0.009 (3)	0.015 (3)
C24	0.051 (3)	0.042 (3)	0.038 (3)	0.014 (3)	0.010 (2)	0.006 (2)
I1	0.0620 (4)	0.0660 (4)	0.0568 (4)	0.0341 (3)	−0.0025 (3)	−0.0116 (3)
I2	0.0716 (3)	0.0742 (3)	0.0942 (4)	0.0167 (3)	0.0177 (3)	−0.0173 (3)
N1	0.035 (2)	0.033 (2)	0.032 (2)	0.0074 (18)	0.0092 (18)	0.0063 (18)
O2	0.040 (2)	0.052 (2)	0.059 (2)	0.0169 (17)	0.0231 (17)	0.0202 (19)
O1	0.0338 (19)	0.051 (2)	0.045 (2)	0.0096 (16)	0.0002 (15)	0.0119 (17)
P1	0.0285 (6)	0.0367 (7)	0.0316 (7)	0.0103 (5)	0.0035 (5)	0.0051 (5)
P2	0.0359 (7)	0.0367 (7)	0.0339 (7)	0.0137 (6)	0.0117 (5)	0.0090 (5)

Geometric parameters (Å, º)

C1—C6	1.380 (7)	C14—H14	0.9300
C1—C2	1.383 (7)	C15—C16	1.358 (11)
C1—P1	1.791 (5)	C15—H15	0.9300
C2—C3	1.366 (8)	C16—C17	1.354 (11)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.370 (10)	C17—C18	1.395 (9)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.355 (10)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.378 (7)
C5—C6	1.378 (9)	C19—C24	1.393 (7)
C5—H5	0.9300	C19—P2	1.792 (5)
C6—H6	0.9300	C20—C21	1.378 (8)
C7—C8	1.381 (7)	C20—H20	0.9300
C7—C12	1.383 (7)	C21—C22	1.365 (8)
C7—P1	1.776 (5)	C21—H21	0.9300
C8—C9	1.371 (8)	C22—C23	1.364 (8)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.362 (10)	C23—C24	1.373 (7)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.365 (9)	C24—H24	0.9300
C10—H10	0.9300	I1—I2	2.9130 (6)
C11—C12	1.383 (8)	N1—P1	1.641 (4)
C11—H11	0.9300	N1—P2	1.669 (4)
C12—H12	0.9300	N1—H1	0.86 (4)
C13—C18	1.385 (7)	O2—P2	1.493 (4)
C13—C14	1.385 (8)	O1—P1	1.516 (3)
C13—P2	1.791 (5)	O1—H1A	0.82
C14—C15	1.379 (8)
C6—C1—C2	119.5 (5)	C17—C16—C15	121.3 (7)
C6—C1—P1	120.7 (4)	C17—C16—H16	119.3
C2—C1—P1	119.7 (4)	C15—C16—H16	119.3
C3—C2—C1	120.1 (6)	C16—C17—C18	120.2 (7)
C3—C2—H2	120.0	C16—C17—H17	119.9
C1—C2—H2	120.0	C18—C17—H17	119.9
C2—C3—C4	120.1 (6)	C13—C18—C17	119.1 (7)
C2—C3—H3	120.0	C13—C18—H18	120.4
C4—C3—H3	120.0	C17—C18—H18	120.4
C5—C4—C3	120.4 (6)	C20—C19—C24	119.7 (5)
C5—C4—H4	119.8	C20—C19—P2	123.5 (4)
C3—C4—H4	119.8	C24—C19—P2	116.8 (4)
C4—C5—C6	120.5 (7)	C19—C20—C21	119.5 (5)
C4—C5—H5	119.8	C19—C20—H20	120.3
C6—C5—H5	119.8	C21—C20—H20	120.3
C5—C6—C1	119.5 (6)	C22—C21—C20	120.5 (6)
C5—C6—H6	120.2	C22—C21—H21	119.7
C1—C6—H6	120.2	C20—C21—H21	119.7
C8—C7—C12	119.7 (5)	C23—C22—C21	120.4 (5)
C8—C7—P1	120.1 (4)	C23—C22—H22	119.8
C12—C7—P1	120.2 (4)	C21—C22—H22	119.8
C9—C8—C7	119.8 (6)	C22—C23—C24	120.2 (5)
C9—C8—H8	120.1	C22—C23—H23	119.9
C7—C8—H8	120.1	C24—C23—H23	119.9
C10—C9—C8	120.7 (6)	C23—C24—C19	119.7 (5)
C10—C9—H9	119.7	C23—C24—H24	120.2
C8—C9—H9	119.7	C19—C24—H24	120.2
C9—C10—C11	120.0 (6)	I2—I1—I2	180.0
C9—C10—H10	120.0	P1—N1—P2	133.4 (3)
C11—C10—H10	120.0	P1—N1—H1	113 (3)
C10—C11—C12	120.5 (6)	P2—N1—H1	113 (3)
C10—C11—H11	119.8	P1—O1—H1A	109.5
C12—C11—H11	119.8	O1—P1—N1	113.0 (2)
C11—C12—C7	119.3 (6)	O1—P1—C7	107.2 (2)
C11—C12—H12	120.3	N1—P1—C7	110.3 (2)
C7—C12—H12	120.3	O1—P1—C1	112.0 (2)
C18—C13—C14	119.4 (5)	N1—P1—C1	103.6 (2)
C18—C13—P2	118.3 (5)	C7—P1—C1	110.7 (2)
C14—C13—P2	122.4 (4)	O2—P2—N1	111.7 (2)
C15—C14—C13	120.4 (6)	O2—P2—C13	111.6 (2)
C15—C14—H14	119.8	N1—P2—C13	105.7 (2)
C13—C14—H14	119.8	O2—P2—C19	111.4 (2)
C16—C15—C14	119.5 (7)	N1—P2—C19	107.0 (2)
C16—C15—H15	120.2	C13—P2—C19	109.2 (2)
C14—C15—H15	120.2
C6—C1—C2—C3	1.2 (8)	P2—C19—C24—C23	−179.1 (4)
P1—C1—C2—C3	178.4 (4)	P2—N1—P1—O1	−59.5 (4)
C1—C2—C3—C4	−1.0 (10)	P2—N1—P1—C7	60.5 (4)
C2—C3—C4—C5	0.5 (12)	P2—N1—P1—C1	179.1 (3)
C3—C4—C5—C6	−0.2 (14)	C8—C7—P1—O1	178.3 (4)
C4—C5—C6—C1	0.4 (12)	C12—C7—P1—O1	−2.6 (5)
C2—C1—C6—C5	−1.0 (9)	C8—C7—P1—N1	54.9 (5)
P1—C1—C6—C5	−178.1 (6)	C12—C7—P1—N1	−126.0 (4)
C12—C7—C8—C9	−1.1 (8)	C8—C7—P1—C1	−59.2 (5)
P1—C7—C8—C9	178.0 (5)	C12—C7—P1—C1	119.9 (4)
C7—C8—C9—C10	1.7 (10)	C6—C1—P1—O1	105.7 (5)
C8—C9—C10—C11	−0.7 (10)	C2—C1—P1—O1	−71.4 (5)
C9—C10—C11—C12	−0.8 (10)	C6—C1—P1—N1	−132.2 (5)
C10—C11—C12—C7	1.3 (9)	C2—C1—P1—N1	50.7 (5)
C8—C7—C12—C11	−0.4 (8)	C6—C1—P1—C7	−14.0 (5)
P1—C7—C12—C11	−179.5 (4)	C2—C1—P1—C7	168.9 (4)
C18—C13—C14—C15	1.2 (9)	P1—N1—P2—O2	−131.9 (3)
P2—C13—C14—C15	−178.8 (5)	P1—N1—P2—C13	106.6 (4)
C13—C14—C15—C16	−1.9 (10)	P1—N1—P2—C19	−9.7 (4)
C14—C15—C16—C17	1.2 (11)	C18—C13—P2—O2	22.7 (5)
C15—C16—C17—C18	0.2 (11)	C14—C13—P2—O2	−157.3 (4)
C14—C13—C18—C17	0.2 (8)	C18—C13—P2—N1	144.3 (4)
P2—C13—C18—C17	−179.8 (4)	C14—C13—P2—N1	−35.7 (5)
C16—C17—C18—C13	−0.9 (9)	C18—C13—P2—C19	−100.9 (4)
C24—C19—C20—C21	1.3 (9)	C14—C13—P2—C19	79.1 (5)
P2—C19—C20—C21	178.7 (5)	C20—C19—P2—O2	−153.2 (4)
C19—C20—C21—C22	−0.6 (10)	C24—C19—P2—O2	24.3 (5)
C20—C21—C22—C23	0.2 (11)	C20—C19—P2—N1	84.4 (5)
C21—C22—C23—C24	−0.5 (10)	C24—C19—P2—N1	−98.1 (4)
C22—C23—C24—C19	1.2 (8)	C20—C19—P2—C13	−29.5 (5)
C20—C19—C24—C23	−1.6 (8)	C24—C19—P2—C13	148.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O1^i	0.82	1.71	2.411 (5)	143
N1—H1···O2^ii	0.86 (4)	1.90 (4)	2.726 (5)	161

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