Polymorphic form of 1,3,5-tris­[(di­phenyl­phosphine oxide)­methyl]­benzene aceto­nitrile solvate mono­hydrate

The title compound, benzene-1,3,5-triyl­tris­methyl­enetris­(di­phenyl­phosphine oxide) aceto­nitrile solvate monohydrate, C₄₅H₃₉O₃P₃·C₂H₃N·H₂O, forms two polymorphs: (I), which crystallizes in the triclinic space group P1, and (II), which crystallizes in the monoclinic space group Pn. The crystal and molecular structures of (I) were previously determined. The results of the crystal structure determination of (II) are presented here. The overall arrangement of two of the di­phenyl­phosphine oxide substituents is determined by strong hydrogen bonds O_water—H...O_oxide. All three P atoms adopt distorted tetrahedral geometry, with C—P—C angles equal to or smaller than tetrahedral and O—P—C angles greater than tetrahedral. All three di­phenyl­phosphine oxide substituents are stabilized by weak C_phenyl—H...O_oxide hydrogen bonds. For each substituent, one of the phenyl rings is almost coplanar with the P=O bond.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.013 Å
• H-atom completeness 94%
• R factor = 0.079
• wR factor = 0.164
• Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_213  Alert C Atom  C24    has ADP max/min Ratio ...........       3.10

PLAT_213  Alert C Atom  C25    has ADP max/min Ratio ...........       3.10

PLAT_213  Alert C Atom  C26    has ADP max/min Ratio ...........       3.30

PLAT_321  Alert C Check Hybridisation of  C(98)  in solvent/ion           ?

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_site* data.
          Atom count from _chemical_formula_sum:C47 H44 N1 O4 P3
          Atom count from the _atom_site data:  C47 H41 N1 O4 P3

CELLZ_01
         From the CIF: _cell_formula_units_Z    2
         From the CIF: _chemical_formula_sum  C47 H44 N O4 P3
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C         94.00     94.00    0.00
         H         88.00     82.00    6.00
         N          2.00      2.00    0.00
         O          8.00      8.00    0.00
         P          6.00      6.00    0.00
          Difference between formula and atom_site contents detected.
          WARNING: H atoms missing from atom site list. Is this intentional?

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.24
         From the CIF: _reflns_number_total               6643
         Count of symmetry unique reflns         3712
         Completeness (_total/calc)            178.96%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2931
         Fraction of Friedel pairs measured     0.790
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 4 Alert Level C = Please check

---

S1. Comment

The crystal and molecular structures of the title compound crystallizing in the P1 space group were previously determined [(I) hereafter; Cambridge Structural Database (CSD; Allen & Kennard, 1993) refcode GOKQAY (Pietrusiewicz et al., 1998)]. Since the crystal structure of (I) had two pairs of only slightly different molecules in the independent part of the unit cell, and the net constants were close to monoclinic system, we tried to obtain a second polymorph of (I), but all attempts failed. The crystals were stored in the dark at 293 K. After four years, we found that the crystals had changed in appearance. The colourless crystals of (I) had become pale pink. Thus, we decided to redetermine the crystal structure of the (I). Measurement of the unit-cell parameters revealed the monoclinic crystal system (II).

The perspective view of (II) and the atomic numbering scheme are shown in Fig. 1. A l l interatomic distances can be considered as normal. We could not localize the H atoms of the acetonitrile molecule, probably because of the fully disordered methyl group. These H atoms are not involved in any hydrogen bond which will be able to provide additional stabilization [the shortest methyl group carbon to nearest atom distance is 3.645 (12) Å]. The phenyl group including the C22 atom shows signs of disorder, but invoking this model did not improve the quality of the refinement; therefore, the model was not applied. The overall molecular geometry of (II) is similar to that of (I) (Pietrusiewicz et al., 1998). The weighted r.m.s. deviation for all atoms in (II) and the first and second molecules of (I) are 0.146 (3) and 0.154 (4) Å, respectively. Superposition of the two molecules, i.e. (II) and one of the molecules of (I), is shown in Fig. 2. The overall arrangement of the diphenylphosphine oxide substituents (best described by torsion angles, see Table 1) indicated by the P1 and P3 atoms is imposed by strong O_water—H···O_oxide hydrogen bonds (for details, see Table 2). These also affect the dihedral angle between the central benzene ring and P—CH₂C_benzene which amounts to 59.7 (3) and 58.9 (3)° for the branches indicated by the P1 and P3 atoms, and 76.2 (4) for the branch indicated by the P2 atom.

The phenyl rings make angles of 67.0 (3), 78.8 (3) and 76.6 (2)° with the substituents indicated by the P1, P2 and P3 atoms, respectively. All the P atoms adopt distorted tetrahedral geometry, with C—P—C angles equal or smaller than tetrahedral and O—P—C angles greater than tetrahedral (Table 1). It is possible to suggest that the steric effect imposed by the phenyl groups has no greater importance. All three diphenylphosphine oxide substituents are stabilized by weak hydrogen bonds C_phenyl—H···O_oxide (Table 2). For each substituent, one of the phenyl rings is almost coplanar with the P═O bond. The central benzene ring makes dihedral angles of 60.7 (3), 72.1 (2), 78.7 (3), 27.6 (3), 10.5 (2) and 82.8 (2)° with the phenyl rings indicated by the C10, C15, C22, C28, C34 and C40 atoms, respectively; the respective P atoms deviate by 0.14 (1), 0.04 (1), 0.21 (1), 0.07 (1), 0.06 (1) and 0.00 (1) Å from the indicated phenyl rings. There are no unusual intermolecular short contacts except for the hydrogen bonds described in Table 2.

S2. Experimental

The title compound was prepared according to the method of Pietrusiewicz et al. (1998) and stored in the dark at 293 K for four years.

Computing details

Data collection: CrysAlis CCD (UNIL IC & Kuma, 2000); cell refinement: CrysAlis RED (UNIL IC & Kuma, 2000); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (II). Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. Superposition of the molecules of (I) and (II). The molecule of (I) is indicated by dashed lines. H atoms have been omitted for clarity.

benzene-1,3,5-triyltrismethylenetris(diphenylphosphine oxide) acetonitrile solvate monohydrate

Crystal data

C45H39O3P3·C2H3N·H2O	F(000) = 820
Mr = 779.74	Dx = 1.266 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 15.3382 (14) Å	Cell parameters from 8473 reflections
b = 8.6418 (9) Å	θ = 2–22°
c = 15.9748 (11) Å	µ = 0.19 mm^−1
β = 105.034 (10)°	T = 291 K
V = 2045.0 (3) Å^3	Pyramid, pale pink
Z = 2	0.60 × 0.40 × 0.40 mm

Data collection

Kuma KM4-CCD diffractometer	6643 independent reflections
Radiation source: fine-focus sealed tube	6532 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
ω scans	θmax = 25.2°, θmin = 3.5°
Absorption correction: numerical (X-RED; Stoe & Cie, 1999)	h = −18→18
Tmin = 0.894, Tmax = 0.928	k = −10→10
20214 measured reflections	l = −19→18

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.079	w = 1/[σ^2(Fo^2) + (0.0113P)^2 + 5.8292P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.164	(Δ/σ)max = 0.003
S = 1.08	Δρmax = 0.29 e Å^−3
6643 reflections	Δρmin = −0.42 e Å^−3
497 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0083 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.24 (15)

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
P1	−0.89339 (10)	−0.96860 (17)	−0.31681 (10)	0.0421 (3)
P2	−0.74371 (11)	−0.77740 (19)	−0.71926 (11)	0.0489 (4)
P3	−0.62228 (12)	−0.43955 (18)	−0.34069 (13)	0.0543 (4)
O1	−0.8595 (3)	−0.8535 (5)	−0.2459 (3)	0.0549 (11)
O2	−0.6797 (4)	−0.6471 (7)	−0.6904 (4)	0.0841 (18)
O3	−0.6191 (3)	−0.5182 (5)	−0.2568 (3)	0.0649 (13)
C1	−0.8119 (4)	−0.8575 (7)	−0.4433 (4)	0.0409 (12)
C2	−0.8334 (4)	−0.8705 (7)	−0.5331 (4)	0.0451 (14)
H2	−0.8548	−0.9642	−0.5591	0.054*
C3	−0.8236 (4)	−0.7484 (7)	−0.5838 (4)	0.0460 (14)
C4	−0.7914 (4)	−0.6084 (7)	−0.5443 (4)	0.0486 (14)
H4	−0.7857	−0.5240	−0.5786	0.058*
C5	−0.7679 (4)	−0.5925 (7)	−0.4557 (4)	0.0447 (13)
C6	−0.7793 (4)	−0.7163 (6)	−0.4047 (4)	0.0460 (14)
H6	−0.7653	−0.7057	−0.3448	0.055*
C7	−0.8193 (4)	−0.9931 (7)	−0.3874 (4)	0.0462 (14)
H7A	−0.7594	−1.0177	−0.3519	0.055*
H7B	−0.8402	−1.0814	−0.4247	0.055*
C8	−0.8437 (4)	−0.7613 (8)	−0.6824 (4)	0.0539 (16)
H8A	−0.8773	−0.6706	−0.7085	0.065*
H8B	−0.8814	−0.8513	−0.7015	0.065*
C9	−0.7334 (4)	−0.4362 (7)	−0.4158 (4)	0.0514 (15)
H9A	−0.7760	−0.3961	−0.3857	0.062*
H9B	−0.7322	−0.3647	−0.4623	0.062*
C10	−0.8994 (4)	−1.1607 (7)	−0.2757 (3)	0.0399 (12)
C11	−0.9778 (6)	−1.2482 (9)	−0.2949 (7)	0.088 (3)
H11	−1.0321	−1.2063	−0.3268	0.105*
C12	−0.9733 (7)	−1.3976 (10)	−0.2658 (8)	0.119 (4)
H12	−1.0256	−1.4571	−0.2803	0.143*
C13	−0.8980 (6)	−1.4623 (9)	−0.2179 (6)	0.073 (2)
H13	−0.8982	−1.5640	−0.1989	0.087*
C14	−0.8217 (6)	−1.3783 (9)	−0.1977 (5)	0.073 (2)
H14	−0.7681	−1.4226	−0.1658	0.088*
C15	−0.8232 (5)	−1.2258 (9)	−0.2243 (5)	0.073 (2)
H15	−0.7711	−1.1664	−0.2068	0.088*
C16	−1.0023 (4)	−0.9187 (7)	−0.3845 (4)	0.0441 (13)
C17	−1.0510 (5)	−0.8008 (8)	−0.3574 (6)	0.068 (2)
H17	−1.0262	−0.7486	−0.3058	0.082*
C18	−1.1356 (6)	−0.7621 (11)	−0.4071 (7)	0.094 (3)
H18	−1.1683	−0.6842	−0.3889	0.113*
C19	−1.1724 (6)	−0.8396 (12)	−0.4849 (6)	0.086 (3)
H19	−1.2290	−0.8114	−0.5190	0.103*
C20	−1.1273 (6)	−0.9531 (13)	−0.5103 (6)	0.094 (3)
H20	−1.1541	−1.0068	−0.5609	0.113*
C21	−1.0414 (5)	−0.9937 (9)	−0.4634 (5)	0.0639 (19)
H21	−1.0096	−1.0702	−0.4839	0.077*
C22	−0.6971 (5)	−0.9642 (9)	−0.6866 (4)	0.0587 (18)
C23	−0.6045 (6)	−0.9815 (15)	−0.6644 (6)	0.106 (4)
H23	−0.5683	−0.8940	−0.6605	0.128*
C24	−0.5641 (11)	−1.124 (2)	−0.6480 (10)	0.167 (9)
H24	−0.5016	−1.1346	−0.6331	0.201*
C25	−0.6174 (17)	−1.248 (2)	−0.6541 (9)	0.182 (12)
H25	−0.5903	−1.3447	−0.6449	0.218*
C26	−0.7071 (13)	−1.2407 (13)	−0.6725 (7)	0.134 (6)
H26	−0.7415	−1.3298	−0.6740	0.161*
C27	−0.7477 (7)	−1.0970 (8)	−0.6894 (5)	0.075 (2)
H27	−0.8103	−1.0899	−0.7029	0.090*
C28	−0.7794 (4)	−0.7865 (7)	−0.8352 (4)	0.0504 (15)
C29	−0.7380 (6)	−0.6925 (10)	−0.8824 (5)	0.073 (2)
H29	−0.6934	−0.6234	−0.8546	0.087*
C30	−0.7632 (6)	−0.7014 (12)	−0.9715 (6)	0.087 (3)
H30	−0.7353	−0.6357	−1.0028	0.104*
C31	−0.8264 (6)	−0.8006 (12)	−1.0156 (5)	0.089 (3)
H31	−0.8402	−0.8056	−1.0757	0.107*
C32	−0.8700 (7)	−0.8946 (15)	−0.9698 (6)	0.113 (4)
H32	−0.9148	−0.9626	−0.9985	0.136*
C33	−0.8454 (6)	−0.8858 (13)	−0.8778 (5)	0.094 (3)
H33	−0.8746	−0.9484	−0.8462	0.113*
C34	−0.5964 (4)	−0.2366 (7)	−0.3248 (5)	0.0589 (18)
C35	−0.5912 (5)	−0.1390 (8)	−0.3930 (6)	0.072 (2)
H35	−0.5990	−0.1800	−0.4483	0.086*
C36	−0.5748 (7)	0.0162 (10)	−0.3798 (7)	0.086 (3)
H36	−0.5717	0.0803	−0.4257	0.103*
C37	−0.5630 (5)	0.0758 (9)	−0.2976 (7)	0.083 (3)
H37	−0.5529	0.1813	−0.2887	0.100*
C38	−0.5659 (5)	−0.0181 (9)	−0.2273 (6)	0.075 (2)
H38	−0.5561	0.0224	−0.1717	0.089*
C39	−0.5840 (5)	−0.1739 (8)	−0.2436 (5)	0.0610 (19)
H39	−0.5879	−0.2381	−0.1980	0.073*
C40	−0.5428 (4)	−0.5204 (7)	−0.3927 (5)	0.0570 (18)
C41	−0.5594 (5)	−0.5348 (9)	−0.4825 (5)	0.071 (2)
H41	−0.6140	−0.4995	−0.5176	0.085*
C42	−0.4960 (6)	−0.6009 (11)	−0.5211 (7)	0.089 (3)
H42	−0.5083	−0.6127	−0.5809	0.107*
C43	−0.4160 (6)	−0.6473 (11)	−0.4679 (8)	0.091 (3)
H43	−0.3727	−0.6904	−0.4923	0.109*
C44	−0.3968 (6)	−0.6327 (12)	−0.3801 (8)	0.095 (3)
H44	−0.3408	−0.6632	−0.3457	0.114*
C45	−0.4618 (5)	−0.5716 (9)	−0.3418 (6)	0.075 (2)
H45	−0.4500	−0.5658	−0.2817	0.090*
C98	−1.0181 (7)	−0.4915 (14)	−0.5388 (7)	0.103 (3)
C99	−0.9645 (6)	−0.3658 (13)	−0.5603 (6)	0.084 (3)
N99	−0.9239 (7)	−0.2692 (11)	−0.5813 (8)	0.122 (4)
O99	−0.6897 (4)	−0.7247 (7)	−0.1543 (3)	0.0827 (16)
H99O	−0.6751	−0.6597	−0.1804	0.124*
H99P	−0.7357	−0.7767	−0.1833	0.124*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0525 (8)	0.0398 (7)	0.0331 (8)	−0.0046 (7)	0.0093 (7)	−0.0009 (6)
P2	0.0561 (9)	0.0514 (9)	0.0383 (9)	−0.0073 (8)	0.0108 (7)	−0.0018 (7)
P3	0.0556 (9)	0.0382 (8)	0.0675 (12)	−0.0049 (7)	0.0133 (8)	−0.0012 (8)
O1	0.071 (3)	0.050 (2)	0.037 (2)	−0.009 (2)	0.001 (2)	−0.0115 (19)
O2	0.095 (4)	0.087 (4)	0.081 (4)	−0.050 (3)	0.043 (3)	−0.036 (3)
O3	0.081 (3)	0.048 (3)	0.061 (3)	−0.010 (2)	0.010 (3)	0.011 (2)
C1	0.046 (3)	0.045 (3)	0.034 (3)	0.004 (2)	0.015 (3)	0.010 (2)
C2	0.056 (4)	0.049 (3)	0.031 (3)	0.001 (3)	0.014 (3)	0.001 (3)
C3	0.051 (3)	0.052 (3)	0.035 (3)	0.006 (3)	0.012 (3)	0.010 (3)
C4	0.052 (3)	0.045 (3)	0.047 (4)	0.005 (3)	0.010 (3)	0.012 (3)
C5	0.041 (3)	0.040 (3)	0.049 (4)	−0.006 (2)	0.005 (3)	−0.001 (3)
C6	0.052 (3)	0.039 (3)	0.048 (4)	−0.009 (3)	0.015 (3)	−0.005 (3)
C7	0.048 (3)	0.041 (3)	0.051 (4)	0.000 (2)	0.014 (3)	0.016 (3)
C8	0.054 (4)	0.074 (4)	0.031 (3)	0.007 (3)	0.006 (3)	0.015 (3)
C9	0.052 (3)	0.043 (3)	0.058 (4)	−0.003 (3)	0.012 (3)	−0.002 (3)
C10	0.048 (3)	0.046 (3)	0.025 (3)	0.000 (3)	0.009 (2)	0.008 (2)
C11	0.064 (5)	0.053 (4)	0.139 (9)	−0.005 (4)	0.015 (5)	0.032 (5)
C12	0.087 (6)	0.052 (5)	0.191 (13)	−0.014 (5)	−0.012 (7)	0.045 (6)
C13	0.089 (6)	0.049 (4)	0.082 (6)	0.003 (4)	0.027 (5)	0.019 (4)
C14	0.088 (6)	0.068 (5)	0.057 (5)	0.010 (4)	0.005 (4)	0.019 (4)
C15	0.068 (5)	0.079 (5)	0.058 (5)	−0.016 (4)	−0.009 (4)	0.033 (4)
C16	0.051 (3)	0.045 (3)	0.038 (3)	0.000 (3)	0.017 (3)	0.004 (3)
C17	0.073 (5)	0.058 (4)	0.078 (6)	0.007 (4)	0.024 (4)	−0.011 (4)
C18	0.068 (5)	0.107 (7)	0.105 (8)	0.035 (5)	0.017 (5)	−0.010 (6)
C19	0.066 (5)	0.104 (7)	0.075 (6)	0.010 (5)	−0.006 (5)	−0.005 (5)
C20	0.076 (6)	0.116 (8)	0.077 (6)	0.014 (5)	−0.006 (5)	−0.014 (6)
C21	0.062 (4)	0.073 (5)	0.046 (4)	0.005 (3)	−0.004 (3)	−0.021 (3)
C22	0.061 (4)	0.082 (5)	0.026 (3)	0.015 (4)	−0.002 (3)	−0.006 (3)
C23	0.073 (6)	0.164 (11)	0.067 (6)	0.046 (6)	−0.010 (5)	−0.037 (6)
C24	0.136 (12)	0.26 (2)	0.076 (8)	0.136 (15)	−0.034 (8)	−0.045 (13)
C25	0.31 (3)	0.174 (17)	0.048 (7)	0.16 (2)	0.015 (13)	0.012 (9)
C26	0.281 (19)	0.081 (7)	0.059 (6)	0.058 (10)	0.075 (10)	0.039 (5)
C27	0.114 (7)	0.049 (4)	0.061 (5)	0.000 (4)	0.022 (5)	0.010 (3)
C28	0.061 (4)	0.050 (3)	0.042 (3)	0.002 (3)	0.015 (3)	0.010 (3)
C29	0.078 (5)	0.080 (5)	0.061 (5)	−0.013 (4)	0.019 (4)	0.016 (4)
C30	0.080 (6)	0.117 (7)	0.064 (6)	−0.003 (5)	0.018 (5)	0.037 (5)
C31	0.080 (6)	0.141 (8)	0.045 (4)	0.007 (6)	0.013 (4)	0.034 (5)
C32	0.094 (7)	0.165 (11)	0.064 (6)	−0.039 (7)	−0.010 (5)	0.010 (7)
C33	0.089 (6)	0.145 (9)	0.035 (4)	−0.047 (6)	−0.010 (4)	0.028 (5)
C34	0.048 (4)	0.036 (3)	0.088 (5)	−0.007 (3)	0.010 (4)	−0.009 (3)
C35	0.082 (5)	0.048 (4)	0.095 (6)	−0.013 (4)	0.040 (5)	−0.001 (4)
C36	0.101 (7)	0.061 (5)	0.105 (7)	−0.008 (5)	0.046 (6)	0.007 (5)
C37	0.072 (5)	0.042 (4)	0.135 (9)	−0.007 (4)	0.028 (6)	−0.003 (5)
C38	0.074 (5)	0.051 (4)	0.093 (6)	−0.001 (4)	0.011 (5)	−0.018 (4)
C39	0.065 (4)	0.042 (3)	0.059 (4)	−0.006 (3)	−0.013 (4)	0.002 (3)
C40	0.051 (4)	0.031 (3)	0.088 (6)	−0.003 (3)	0.018 (4)	−0.001 (3)
C41	0.057 (4)	0.082 (5)	0.077 (5)	0.013 (4)	0.024 (4)	0.001 (4)
C42	0.085 (6)	0.092 (6)	0.105 (7)	−0.003 (5)	0.050 (6)	−0.022 (5)
C43	0.070 (6)	0.091 (7)	0.119 (9)	0.022 (5)	0.037 (6)	0.007 (6)
C44	0.056 (5)	0.102 (7)	0.119 (9)	0.017 (5)	0.009 (5)	0.013 (6)
C45	0.053 (4)	0.066 (5)	0.094 (6)	−0.001 (4)	−0.001 (4)	0.009 (4)
C98	0.097 (7)	0.123 (9)	0.085 (7)	−0.010 (6)	0.020 (6)	0.017 (6)
C99	0.076 (6)	0.095 (7)	0.064 (5)	0.029 (5)	−0.011 (4)	−0.028 (5)
N99	0.114 (8)	0.072 (5)	0.160 (10)	0.008 (5)	0.000 (7)	0.004 (6)
O99	0.096 (4)	0.090 (4)	0.060 (3)	−0.019 (3)	0.015 (3)	0.020 (3)

Geometric parameters (Å, º)

P1—O1	1.496 (4)	C20—H20	0.9300
P1—C16	1.791 (6)	C21—H21	0.9300
P1—C10	1.796 (6)	C22—C27	1.380 (11)
P1—C7	1.809 (6)	C22—C23	1.381 (11)
P2—O2	1.486 (5)	C23—C24	1.376 (18)
P2—C8	1.785 (6)	C23—H23	0.9300
P2—C22	1.787 (7)	C24—C25	1.33 (3)
P2—C28	1.792 (7)	C24—H24	0.9300
P3—O3	1.492 (5)	C25—C26	1.33 (2)
P3—C40	1.786 (7)	C25—H25	0.9300
P3—C34	1.801 (6)	C26—C27	1.384 (13)
P3—C9	1.812 (6)	C26—H26	0.9300
C1—C2	1.392 (8)	C27—H27	0.9300
C1—C6	1.400 (8)	C28—C33	1.366 (10)
C1—C7	1.496 (7)	C28—C29	1.371 (9)
C2—C3	1.361 (8)	C29—C30	1.377 (11)
C2—H2	0.9300	C29—H29	0.9300
C3—C4	1.395 (9)	C30—C31	1.347 (12)
C3—C8	1.529 (8)	C30—H30	0.9300
C4—C5	1.374 (9)	C31—C32	1.377 (12)
C4—H4	0.9300	C31—H31	0.9300
C5—C6	1.382 (8)	C32—C33	1.421 (11)
C5—C9	1.529 (8)	C32—H32	0.9300
C6—H6	0.9300	C33—H33	0.9300
C7—H7A	0.9700	C34—C39	1.373 (10)
C7—H7B	0.9700	C34—C35	1.397 (10)
C8—H8A	0.9700	C35—C36	1.370 (11)
C8—H8B	0.9700	C35—H35	0.9300
C9—H9A	0.9700	C36—C37	1.379 (13)
C9—H9B	0.9700	C36—H36	0.9300
C10—C15	1.363 (9)	C37—C38	1.395 (12)
C10—C11	1.385 (9)	C37—H37	0.9300
C11—C12	1.368 (10)	C38—C39	1.386 (10)
C11—H11	0.9300	C38—H38	0.9300
C12—C13	1.333 (12)	C39—H39	0.9300
C12—H12	0.9300	C40—C45	1.370 (10)
C13—C14	1.343 (11)	C40—C41	1.396 (10)
C13—H13	0.9300	C41—C42	1.400 (10)
C14—C15	1.384 (10)	C41—H41	0.9300
C14—H14	0.9300	C42—C43	1.360 (13)
C15—H15	0.9300	C42—H42	0.9300
C16—C17	1.396 (9)	C43—C44	1.362 (13)
C16—C21	1.405 (9)	C43—H43	0.9300
C17—C18	1.376 (11)	C44—C45	1.402 (12)
C17—H17	0.9300	C44—H44	0.9300
C18—C19	1.395 (12)	C45—H45	0.9300
C18—H18	0.9300	C98—C99	1.457 (15)
C19—C20	1.323 (13)	C99—N99	1.142 (13)
C19—H19	0.9300	O99—H99O	0.7674
C20—C21	1.382 (11)	O99—H99P	0.8627
O1—P1—C16	112.5 (3)	C20—C19—H19	119.8
O1—P1—C10	112.3 (3)	C18—C19—H19	119.8
C16—P1—C10	108.4 (3)	C19—C20—C21	121.5 (9)
O1—P1—C7	113.5 (3)	C19—C20—H20	119.2
C16—P1—C7	106.9 (3)	C21—C20—H20	119.2
C10—P1—C7	102.7 (3)	C20—C21—C16	119.6 (7)
O2—P2—C8	113.2 (3)	C20—C21—H21	120.2
O2—P2—C22	114.3 (4)	C16—C21—H21	120.2
C8—P2—C22	106.7 (3)	C27—C22—C23	116.8 (8)
O2—P2—C28	110.7 (3)	C27—C22—P2	124.3 (6)
C8—P2—C28	106.6 (3)	C23—C22—P2	118.7 (8)
C22—P2—C28	104.7 (3)	C24—C23—C22	121.9 (13)
O3—P3—C40	111.8 (3)	C24—C23—H23	119.0
O3—P3—C34	111.2 (3)	C22—C23—H23	119.0
C40—P3—C34	107.1 (3)	C25—C24—C23	117.8 (16)
O3—P3—C9	114.1 (3)	C25—C24—H24	121.1
C40—P3—C9	109.7 (3)	C23—C24—H24	121.1
C34—P3—C9	102.3 (3)	C24—C25—C26	124.1 (17)
C2—C1—C6	119.1 (5)	C24—C25—H25	118.0
C2—C1—C7	121.2 (6)	C26—C25—H25	118.0
C6—C1—C7	119.6 (5)	C25—C26—C27	118.0 (16)
C3—C2—C1	121.2 (6)	C25—C26—H26	121.0
C3—C2—H2	119.4	C27—C26—H26	121.0
C1—C2—H2	119.4	C22—C27—C26	121.3 (11)
C2—C3—C4	119.0 (5)	C22—C27—H27	119.3
C2—C3—C8	122.2 (6)	C26—C27—H27	119.3
C4—C3—C8	118.8 (5)	C33—C28—C29	119.2 (7)
C5—C4—C3	121.3 (5)	C33—C28—P2	122.0 (5)
C5—C4—H4	119.3	C29—C28—P2	118.8 (6)
C3—C4—H4	119.3	C28—C29—C30	119.3 (8)
C4—C5—C6	119.4 (5)	C28—C29—H29	120.3
C4—C5—C9	119.2 (6)	C30—C29—H29	120.3
C6—C5—C9	121.4 (6)	C31—C30—C29	123.1 (8)
C5—C6—C1	120.0 (6)	C31—C30—H30	118.4
C5—C6—H6	120.0	C29—C30—H30	118.4
C1—C6—H6	120.0	C30—C31—C32	118.7 (8)
C1—C7—P1	116.0 (4)	C30—C31—H31	120.7
C1—C7—H7A	108.3	C32—C31—H31	120.7
P1—C7—H7A	108.3	C31—C32—C33	118.9 (9)
C1—C7—H7B	108.3	C31—C32—H32	120.6
P1—C7—H7B	108.3	C33—C32—H32	120.6
H7A—C7—H7B	107.4	C28—C33—C32	120.8 (8)
C3—C8—P2	112.6 (4)	C28—C33—H33	119.6
C3—C8—H8A	109.1	C32—C33—H33	119.6
P2—C8—H8A	109.1	C39—C34—C35	118.5 (6)
C3—C8—H8B	109.1	C39—C34—P3	119.3 (6)
P2—C8—H8B	109.1	C35—C34—P3	122.2 (6)
H8A—C8—H8B	107.8	C36—C35—C34	121.1 (8)
C5—C9—P3	115.3 (4)	C36—C35—H35	119.5
C5—C9—H9A	108.5	C34—C35—H35	119.5
P3—C9—H9A	108.5	C35—C36—C37	119.1 (9)
C5—C9—H9B	108.5	C35—C36—H36	120.5
P3—C9—H9B	108.5	C37—C36—H36	120.5
H9A—C9—H9B	107.5	C36—C37—C38	121.7 (8)
C15—C10—C11	117.8 (6)	C36—C37—H37	119.1
C15—C10—P1	119.0 (5)	C38—C37—H37	119.1
C11—C10—P1	123.2 (5)	C39—C38—C37	117.4 (8)
C12—C11—C10	118.5 (8)	C39—C38—H38	121.3
C12—C11—H11	120.8	C37—C38—H38	121.3
C10—C11—H11	120.8	C34—C39—C38	122.2 (8)
C13—C12—C11	123.4 (9)	C34—C39—H39	118.9
C13—C12—H12	118.3	C38—C39—H39	118.9
C11—C12—H12	118.3	C45—C40—C41	118.5 (7)
C12—C13—C14	118.9 (7)	C45—C40—P3	118.3 (7)
C12—C13—H13	120.6	C41—C40—P3	123.2 (5)
C14—C13—H13	120.6	C40—C41—C42	121.7 (8)
C13—C14—C15	119.8 (8)	C40—C41—H41	119.1
C13—C14—H14	120.1	C42—C41—H41	119.1
C15—C14—H14	120.1	C43—C42—C41	117.5 (9)
C10—C15—C14	121.5 (7)	C43—C42—H42	121.2
C10—C15—H15	119.3	C41—C42—H42	121.2
C14—C15—H15	119.3	C42—C43—C44	122.3 (9)
C17—C16—C21	118.4 (6)	C42—C43—H43	118.8
C17—C16—P1	118.6 (5)	C44—C43—H43	118.8
C21—C16—P1	123.0 (5)	C43—C44—C45	119.8 (8)
C18—C17—C16	119.9 (8)	C43—C44—H44	120.1
C18—C17—H17	120.0	C45—C44—H44	120.1
C16—C17—H17	120.0	C40—C45—C44	120.0 (9)
C17—C18—C19	120.0 (8)	C40—C45—H45	120.0
C17—C18—H18	120.0	C44—C45—H45	120.0
C19—C18—H18	120.0	N99—C99—C98	176.6 (11)
C20—C19—C18	120.4 (8)	H99O—O99—H99P	113.7
C2—C1—C7—P1	−121.9 (6)	C8—P2—C28—C33	−49.5 (8)
C1—C7—P1—C10	170.6 (5)	C3—C8—P2—O2	−56.7 (6)
C7—P1—C10—C11	−113.6 (7)	O2—P2—C22—C23	−20.7 (7)
C7—P1—C10—C15	65.2 (6)	O2—P2—C22—C27	165.5 (6)
C6—C1—C7—P1	60.7 (7)	O2—P2—C28—C29	8.0 (7)
C1—C7—P1—C16	56.7 (5)	O2—P2—C28—C33	−173.0 (7)
C7—P1—C16—C17	−136.8 (5)	C4—C5—C9—P3	−122.3 (6)
C7—P1—C16—C21	43.8 (6)	C5—C9—P3—C34	169.3 (5)
C1—C7—P1—O1	−68.0 (5)	C9—P3—C34—C35	−60.7 (7)
O1—P1—C10—C11	124.1 (7)	C9—P3—C34—C39	117.3 (6)
O1—P1—C10—C15	−57.1 (6)	C6—C5—C9—P3	60.2 (7)
O1—P1—C16—C17	−11.6 (6)	C5—C9—P3—C40	55.8 (5)
O1—P1—C16—C21	169.0 (5)	C9—P3—C40—C41	17.0 (7)
C2—C3—C8—P2	−102.3 (6)	C9—P3—C40—C45	−162.5 (5)
C3—C8—P2—C22	69.9 (5)	C5—C9—P3—O3	−70.5 (5)
C8—P2—C22—C23	−146.6 (6)	O3—P3—C34—C35	177.1 (6)
C8—P2—C22—C27	39.6 (7)	O3—P3—C34—C39	−4.9 (7)
C4—C3—C8—P2	75.5 (7)	O3—P3—C40—C41	144.6 (6)
C3—C8—P2—C28	−178.6 (5)	O3—P3—C40—C45	−34.9 (6)
C8—P2—C28—C29	131.5 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O99—H99P···O1	0.86	2.02	2.861 (7)	166
O99—H99O···O3	0.77	2.06	2.821 (7)	169
C15—H15···O1	0.93	3.02	3.268 (9)	97
C17—H17···O1	0.93	2.65	3.048 (9)	107
C23—H23···O2	0.93	2.70	3.099 (13)	107
C45—H45···O3	0.93	2.76	3.093 (10)	103
C29—H29···O2	0.93	2.58	2.989 (10)	107
C39—H39···O3	0.93	2.60	3.021 (8)	108