Two tetrahydrofuran solvates of HN(SePPh₂)₂

The X-ray crystal structures of P,P'-imino­bis­(di­phenyl­seleno­phosphine) tetra­hydro­furan solvate, C₂₄H₂₁NP₂Se₂·C₄H₈O, (I), and bis­(tetra­hydro­furan) solvate, C₂₄H₂₁NP₂Se₂·2C₄H₈O, (II), have been determined; (I) has twofold crystallographic symmetry. In each compound, the O atom of one mol­ecule of tetra­hydro­furan is hydrogen bonded to the amide-H atom of HN(SePPh₂)₂. The conformation of the Se-P-N-P-Se chains in (I), (II), and the crystal structure of the unsolvated HN(SePPh₂)₂ are different.

S1. Comment

As part of our work on soluble rare-earth chalcogenide species (Pernin & Ibers, 1997, 1999a or b) we have investigated rare-earth complexes of the imidodiphosphinochalcogenido ligand [N(QPPh₂)₂]^- (Q = S, Se) (Pernin & Ibers, 1999a or b). In addition to η²-coordination through the two chalcogen atoms, the ligand adopts η³-coordination through the two chalcogen atoms and the N atom to the rare-earth atoms. This is in contrast to the previously reported transition- and main group-metal complexes containing the ligand (Bhattacharyya, Novosad et al., 1995; Garcia-Montalvo, Slawin et al., 1997) that typically adopt η²– coordination. In this paper we show that the conformation of the Se—P—N—P—Se chain is sensitive to solvation. \sch

Figs. 1 and 2 show displacement ellipsoid diagrams with atom numbering of compounds (I) and (II). The molecules in (I) have an imposed crystallographic 2 axis. Tables 1, 2 and 3 contain selected bond distances and angles. In (I) and (II), P—Se [2.094 (1) Å for (I); 2.097 (1) Å and 2.099 (1) Å for (II)] and P—N [1.676 (1) Å for (I); 1.690 (2) Å and 1.680 (2) Å for (II)]. Bonding distances are similar to each other and to the P—Se distances of 2.085 (1) Å and 2.101 (1) Å and the P—N distances of 1.678 (4) Å and 1.686 (3) Å in unsolvated HN(SePPh₂)₂. The conformations of the Se—P—N—P—Se chains in the three compounds differ markedly, the Se—P···P—Se 'torsion angles' being 81.75 (3), 179.19 (3) and 154°, respectively. Both (II) and the unsolvated species are approximately anti with respect to that torsion angle whereas (I) is approximately gauche. The S—P···P—S 'torsion angle' is 156° in the unsolvated sulfur analogue, HN(SPPh₂)₂ (Husebye & Maartmann, 1983).

In the structure of the unsolvated species, HN(SePPh₂)₂ molecules are linked by N—H···Se hydrogen bonds to form dimer pairs. In the structure of HN(SPPh₂)₂ there are similar dimers. In each of the present structures, the HN(SePPh₂)₂ molecule is linked to a THF molecule through a N1—H1A···O1 hydrogen bond (Table 2). The N1···O1 distances [2.771 (3) Å for (I) and 2.815 (3) Å for (II)] are similar to the distances in other thf—amide hydrogen-bonded interactions (Etter et al., 1990; Bonamico et al., 1991). The dihedral angle between the hydrogen-bonded thf molecules and the P—N—P plane is 79.3 (1) in (I) and 25.3 (3)° in (II). Some atoms of the thf molecules show large displacement ellipsoids for data collected at 153 K. This may be due to conformational changes between the twist and envelope forms of the five- membered rings (Cremer & Pople, 1975; Luo et al., 1990; Westerhausen et al.,1998). Nonetheless, C—O and C—C bonds are normal in (I) and exhibit some unreasonable distances in (II) (for example C25—C26= 1.330 (6) Å, see Tables 1 and 3 for additional distances and angles). This apparent disorder in the hydrogen-bonded thf molecule in (II) could not be modeled adequately with the superposition of more than one molecule of thf of differing conformation.

P—C bond distances for (I) [1.814 (2) and 1.815 (2) Å] and (II) [1.815 (3), 1.820 (2), 1.812 (3), 1.818 (2) Å] are normal as are the average C—C distances, 1.381 (9) and 1.386 (8) Å.

S2. Experimental

Unsolvated HN(SePPh₂)₂ was prepared by a literature method (Bhattacharya, Slawin et al., 1995). The reaction of more than one equivalent of HN(SePPh₂)₂ with Cp₃Y (Cp = cyclopentadienyl) in thf produces Cp₂Y[N(SePPh₂)₂] in addition to leaving unreacted HN(SePPh₂)₂ in solution (Pernin & Ibers, 1999a or b). Upon dilution of the thf solution with pentane, crystals of HN(SePPh₂)₂ containing one, (I), and two, (II), molecules of thf were cyrstallized at 258 K.

S3. Refinement

Data collections were performed on crystals coated in immersion oil and frozen at 153 K in Nylon loops. Both structures were solved by standard Patterson methods and refined by full-matrix least-squares methods (Sheldrick, 1997). Anisotropic displacement parameters were used for all non-hydrogen atoms. H atoms were placed at calculated positions (0.88 Å for amide protons; 0.95 Å for aliphatic protons; 0.99 Å for aromatic protons) and refined with a riding model. The U_iso value for a given H atom was assigned as 1.2 times the U_iso of the atom to which it is attached.

Computing details

For both compounds, data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXTL97.

Figures

	Fig. 1. Structure of (I) showing 50% probability displacement ellipsoids and H atoms, in idealized positions, as small circles.
	Fig. 2. Structure of (II) showing 50% probability displacement ellipsoids and H atoms, in idealized positions, as small circles.

(I) 'N-(diphenylphosphinoselenoyl)-P,P-diphenyl- tetrahydrofuran solvate'

Crystal data

C24H21NP2Se2·C4H8O	Dx = 1.528 Mg m^−3
Mr = 615.38	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212	Cell parameters from 8192 reflections
a = 10.121 (3) Å	θ = 2.2–28.5°
c = 26.118 (10) Å	µ = 2.91 mm^−1
V = 2675.5 (14) Å^3	T = 153 K
Z = 4	Block, colourless
F(000) = 1240	0.30 × 0.20 × 0.10 mm

Data collection

Bruker Smart 1000 CCD diffractometer	3237 independent reflections
Radiation source: standard-focus sealed tube	2891 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 28.5°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −13→6
Tmin = 0.776, Tmax = 1.000	k = −12→12
17047 measured reflections	l = −31→33

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.022	H-atom parameters constrained
wR(F^2) = 0.059	w = 1/[σ^2(Fo^2) + (0.04Fo^2)^2]
S = 0.97	(Δ/σ)max = 0.003
3237 reflections	Δρmax = 0.25 e Å^−3
155 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: Patterson	Absolute structure parameter: −0.022 (8)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	1.29704 (2)	−0.00007 (2)	0.990431 (7)	0.03009 (7)
P1	1.10989 (5)	−0.03353 (5)	0.958782 (18)	0.02294 (11)
N1	0.98426 (16)	−0.01574 (16)	1.0000	0.0239 (5)
H1A	0.9228	−0.0772	1.0000	0.029*
C1	1.0855 (2)	−0.2004 (2)	0.93526 (7)	0.0258 (4)
C2	1.1748 (2)	−0.2984 (2)	0.94727 (8)	0.0344 (5)
H2A	1.2499	−0.2785	0.9677	0.041*
C3	1.1550 (3)	−0.4265 (2)	0.92948 (9)	0.0439 (6)
H3A	1.2157	−0.4943	0.9384	0.053*
C4	1.0486 (3)	−0.4551 (2)	0.89910 (9)	0.0454 (7)
H4A	1.0358	−0.5426	0.8869	0.054*
C5	0.9605 (3)	−0.3581 (3)	0.88625 (9)	0.0463 (6)
H5A	0.8868	−0.3782	0.8651	0.056*
C6	0.9788 (2)	−0.2302 (2)	0.90406 (9)	0.0363 (5)
H6A	0.9179	−0.1628	0.8948	0.044*
C7	1.0746 (2)	0.06911 (19)	0.90346 (7)	0.0249 (4)
C8	0.9471 (2)	0.1036 (2)	0.88988 (8)	0.0308 (5)
H8A	0.8751	0.0786	0.9111	0.037*
C9	0.9243 (2)	0.1747 (2)	0.84521 (8)	0.0329 (5)
H9A	0.8366	0.1974	0.8357	0.039*
C10	1.0286 (2)	0.2121 (2)	0.81494 (9)	0.0383 (5)
H10A	1.0128	0.2615	0.7846	0.046*
C11	1.1554 (2)	0.1790 (2)	0.82807 (9)	0.0384 (6)
H11A	1.2271	0.2059	0.8071	0.046*
C12	1.1788 (2)	0.1058 (2)	0.87223 (7)	0.0305 (4)
H12A	1.2665	0.0809	0.8810	0.037*
C13	0.8046 (3)	−0.3390 (3)	1.02040 (14)	0.0625 (8)
H13A	0.8408	−0.3351	1.0556	0.075*
H13B	0.8655	−0.3918	0.9989	0.075*
C14	0.6718 (3)	−0.3994 (3)	1.02078 (12)	0.0613 (8)
H14A	0.6278	−0.3860	1.0542	0.074*
H14B	0.6767	−0.4953	1.0135	0.074*
O1	0.79066 (16)	−0.20934 (16)	1.0000	0.0472 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.02299 (11)	0.03843 (13)	0.02885 (10)	−0.00390 (8)	−0.00195 (7)	−0.00069 (9)
P1	0.0228 (2)	0.0249 (3)	0.0211 (2)	−0.00223 (19)	0.00053 (19)	−0.00132 (18)
N1	0.0236 (7)	0.0236 (7)	0.0245 (11)	−0.0064 (10)	0.0035 (6)	−0.0035 (6)
C1	0.0319 (11)	0.0250 (10)	0.0204 (8)	−0.0002 (8)	0.0022 (8)	−0.0025 (8)
C2	0.0437 (14)	0.0319 (11)	0.0276 (10)	0.0047 (10)	−0.0021 (9)	−0.0019 (9)
C3	0.0620 (17)	0.0327 (13)	0.0371 (12)	0.0131 (12)	0.0024 (11)	−0.0036 (10)
C4	0.0734 (19)	0.0282 (12)	0.0346 (12)	−0.0069 (11)	0.0022 (12)	−0.0080 (9)
C5	0.0629 (18)	0.0357 (13)	0.0403 (13)	−0.0111 (12)	−0.0140 (12)	−0.0033 (10)
C6	0.0436 (14)	0.0284 (11)	0.0369 (12)	−0.0034 (10)	−0.0097 (10)	−0.0003 (9)
C7	0.0286 (11)	0.0234 (10)	0.0228 (9)	−0.0017 (8)	−0.0007 (8)	−0.0032 (8)
C8	0.0296 (11)	0.0323 (12)	0.0305 (11)	−0.0007 (9)	−0.0001 (8)	−0.0010 (9)
C9	0.0338 (12)	0.0313 (12)	0.0334 (11)	0.0041 (9)	−0.0067 (9)	0.0000 (9)
C10	0.0507 (15)	0.0369 (12)	0.0273 (10)	0.0022 (11)	−0.0004 (10)	0.0057 (9)
C11	0.0411 (13)	0.0407 (14)	0.0334 (11)	−0.0009 (11)	0.0075 (10)	0.0079 (10)
C12	0.0288 (12)	0.0324 (12)	0.0302 (10)	−0.0008 (9)	0.0041 (8)	0.0026 (9)
C13	0.0526 (17)	0.0487 (17)	0.086 (2)	−0.0050 (13)	−0.0058 (17)	0.0228 (15)
C14	0.0650 (19)	0.0547 (17)	0.0643 (18)	−0.0260 (15)	−0.0044 (14)	0.0119 (15)
O1	0.0368 (8)	0.0368 (8)	0.0678 (17)	−0.0131 (11)	−0.0062 (9)	0.0062 (9)

Geometric parameters (Å, º)

Se1—P1	2.0942 (7)	C5—C6	1.387 (3)
P1—N1	1.6757 (12)	C7—C8	1.383 (3)
P1—C1	1.814 (2)	C7—C12	1.384 (3)
P1—C7	1.815 (2)	C8—C9	1.391 (3)
N1—P1^i	1.6757 (12)	C9—C10	1.372 (3)
N1—O1	2.771 (3)	C10—C11	1.369 (3)
C1—C2	1.378 (3)	C11—C12	1.391 (3)
C1—C6	1.386 (3)	C13—O1	1.424 (3)
C2—C3	1.392 (3)	C13—C14	1.477 (4)
C3—C4	1.369 (4)	C14—C14^i	1.490 (6)
C4—C5	1.368 (4)	O1—C13^i	1.424 (3)
N1—P1—C1	102.38 (10)	C4—C5—C6	120.0 (2)
N1—P1—C7	107.50 (7)	C1—C6—C5	120.2 (2)
C1—P1—C7	103.69 (9)	C8—C7—C12	119.49 (19)
N1—P1—Se1	114.54 (6)	C8—C7—P1	122.13 (16)
C1—P1—Se1	114.03 (7)	C12—C7—P1	118.23 (16)
C7—P1—Se1	113.54 (7)	C7—C8—C9	120.1 (2)
P1^i—N1—P1	125.15 (14)	C10—C9—C8	119.9 (2)
P1^i—N1—O1	117.42 (7)	C11—C10—C9	120.6 (2)
P1—N1—O1	117.42 (7)	C10—C11—C12	119.9 (2)
C2—C1—C6	119.3 (2)	C7—C12—C11	120.1 (2)
C2—C1—P1	120.24 (17)	O1—C13—C14	107.1 (2)
C6—C1—P1	120.49 (17)	C13—C14—C14^i	103.61 (17)
C1—C2—C3	120.0 (2)	C13^i—O1—C13	108.9 (3)
C4—C3—C2	120.3 (2)	C13^i—O1—N1	125.57 (14)
C5—C4—C3	120.2 (2)	C13—O1—N1	125.57 (14)
C1—P1—N1—P1^i	169.78 (7)	C1—P1—C7—C8	82.68 (19)
C7—P1—N1—P1^i	−81.36 (7)	Se1—P1—C7—C8	−153.04 (16)
Se1—P1—N1—P1^i	45.83 (3)	N1—P1—C7—C12	159.26 (17)
C1—P1—N1—O1	−10.22 (7)	C1—P1—C7—C12	−92.79 (18)
C7—P1—N1—O1	98.64 (7)	Se1—P1—C7—C12	31.49 (19)
Se1—P1—N1—O1	−134.17 (3)	C12—C7—C8—C9	−0.1 (3)
N1—P1—C1—C2	−112.36 (16)	P1—C7—C8—C9	−175.56 (16)
C7—P1—C1—C2	135.90 (17)	C7—C8—C9—C10	−0.8 (3)
Se1—P1—C1—C2	11.93 (19)	C8—C9—C10—C11	0.6 (4)
N1—P1—C1—C6	69.19 (18)	C9—C10—C11—C12	0.5 (4)
C7—P1—C1—C6	−42.56 (19)	C8—C7—C12—C11	1.3 (3)
Se1—P1—C1—C6	−166.52 (15)	P1—C7—C12—C11	176.87 (18)
C6—C1—C2—C3	−2.1 (3)	C10—C11—C12—C7	−1.5 (4)
P1—C1—C2—C3	179.46 (17)	O1—C13—C14—C14^i	25.8 (4)
C1—C2—C3—C4	1.4 (4)	C14—C13—O1—C13^i	−10.10 (17)
C2—C3—C4—C5	−0.3 (4)	C14—C13—O1—N1	169.90 (17)
C3—C4—C5—C6	−0.1 (4)	P1^i—N1—O1—C13^i	73.75 (19)
C2—C1—C6—C5	1.6 (3)	P1—N1—O1—C13^i	−106.25 (19)
P1—C1—C6—C5	−179.90 (19)	P1^i—N1—O1—C13	−106.25 (19)
C4—C5—C6—C1	−0.5 (4)	P1—N1—O1—C13	73.75 (19)
N1—P1—C7—C8	−25.3 (2)	Se1—P1—P1^i—Se1^i	81.75 (3)

Symmetry code: (i) y+1, x−1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	1.89	2.771 (3)	180

(II) 'N-(diphenylphosphinoselenoyl)-P,P-diphenyl- tetrahydrofuran solvate'

Crystal data

C24H21NP2Se2·2C4H8O	Z = 2
Mr = 687.49	F(000) = 700
Triclinic, P1	Dx = 1.471 Mg m^−3
a = 8.796 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.248 (3) Å	Cell parameters from 7641 reflections
c = 13.864 (3) Å	θ = 1.5–28.3°
α = 97.832 (4)°	µ = 2.52 mm^−1
β = 102.673 (4)°	T = 153 K
γ = 94.545 (4)°	Block, colourless
V = 1551.6 (6) Å^3	0.40 × 0.20 × 0.10 mm

Data collection

Bruker Smart 1000 CCD diffractometer	7046 independent reflections
Radiation source: standard-focus sealed tube	5578 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.741, Tmax = 1.000	k = −17→17
14636 measured reflections	l = −18→17

Refinement

Refinement on F^2	Primary atom site location: Patterson
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.24	w = 1/[σ^2(Fo^2) + (0.04Fo^2)^2]
7046 reflections	(Δ/σ)max = 0.010
352 parameters	Δρmax = 1.11 e Å^−3
0 restraints	Δρmin = −1.17 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	−0.97690 (3)	0.73537 (2)	−0.028395 (19)	0.03124 (8)
Se2	−0.79351 (3)	0.74032 (2)	−0.432007 (19)	0.03581 (9)
P1	−0.83080 (7)	0.67341 (5)	−0.11638 (4)	0.02149 (13)
P2	−0.90042 (7)	0.76748 (5)	−0.31108 (4)	0.02327 (14)
N1	−0.7895 (2)	0.73987 (15)	−0.20496 (14)	0.0236 (4)
H1A	−0.6904	0.7650	−0.1932	0.028*
C1	−0.9082 (3)	0.54645 (19)	−0.18486 (17)	0.0249 (5)
C2	−1.0282 (3)	0.4902 (2)	−0.15798 (19)	0.0319 (6)
H2A	−1.0651	0.5165	−0.1012	0.038*
C3	−1.0943 (3)	0.3955 (2)	−0.2139 (2)	0.0412 (7)
H3A	−1.1770	0.3576	−0.1956	0.049*
C4	−1.0401 (4)	0.3567 (2)	−0.2958 (2)	0.0446 (8)
H4A	−1.0865	0.2925	−0.3346	0.054*
C5	−0.9192 (4)	0.4105 (2)	−0.3213 (2)	0.0413 (7)
H5A	−0.8810	0.3825	−0.3770	0.050*
C6	−0.8517 (3)	0.5052 (2)	−0.26686 (18)	0.0314 (6)
H6A	−0.7678	0.5419	−0.2851	0.038*
C7	−0.6344 (3)	0.66554 (19)	−0.04324 (17)	0.0250 (5)
C8	−0.5264 (3)	0.6161 (2)	−0.0863 (2)	0.0346 (6)
H8A	−0.5548	0.5854	−0.1547	0.042*
C9	−0.3770 (3)	0.6114 (2)	−0.0295 (3)	0.0463 (8)
H9A	−0.3035	0.5775	−0.0592	0.056*
C10	−0.3347 (3)	0.6555 (3)	0.0693 (2)	0.0473 (8)
H10A	−0.2322	0.6517	0.1076	0.057*
C11	−0.4399 (3)	0.7052 (3)	0.1134 (2)	0.0496 (8)
H11A	−0.4097	0.7364	0.1816	0.060*
C12	−0.5915 (3)	0.7094 (2)	0.05715 (19)	0.0382 (7)
H12A	−0.6652	0.7423	0.0876	0.046*
C13	−1.0922 (3)	0.69482 (19)	−0.33269 (17)	0.0262 (5)
C14	−1.1278 (3)	0.6028 (2)	−0.39839 (18)	0.0315 (6)
H14A	−1.0518	0.5779	−0.4321	0.038*
C15	−1.2738 (3)	0.5468 (2)	−0.4151 (2)	0.0426 (7)
H15A	−1.2967	0.4829	−0.4586	0.051*
C16	−1.3853 (3)	0.5842 (3)	−0.3686 (2)	0.0471 (8)
H16A	−1.4855	0.5459	−0.3807	0.057*
C17	−1.3536 (3)	0.6768 (3)	−0.3044 (2)	0.0438 (7)
H17A	−1.4320	0.7027	−0.2736	0.053*
C18	−1.2047 (3)	0.7322 (2)	−0.28525 (19)	0.0323 (6)
H18A	−1.1808	0.7950	−0.2400	0.039*
C19	−0.9308 (3)	0.90087 (19)	−0.28247 (18)	0.0271 (5)
C20	−0.9827 (3)	0.9556 (2)	−0.3600 (2)	0.0392 (7)
H20A	−0.9990	0.9234	−0.4276	0.047*
C21	−1.0106 (4)	1.0570 (2)	−0.3389 (2)	0.0529 (9)
H21A	−1.0491	1.0935	−0.3919	0.064*
C22	−0.9823 (4)	1.1049 (2)	−0.2406 (2)	0.0542 (9)
H22A	−0.9983	1.1749	−0.2262	0.065*
C23	−0.9308 (4)	1.0513 (2)	−0.1635 (2)	0.0497 (8)
H23A	−0.9121	1.0843	−0.0961	0.060*
C24	−0.9061 (3)	0.9493 (2)	−0.18416 (19)	0.0380 (6)
H24A	−0.8721	0.9124	−0.1307	0.046*
C25	−0.5005 (5)	0.9567 (4)	−0.2162 (3)	0.1024 (19)
H25A	−0.5189	0.9292	−0.2883	0.123*
H25B	−0.5825	1.0017	−0.2070	0.123*
C26	−0.3596 (7)	1.0102 (3)	−0.1846 (3)	0.117 (2)
H26A	−0.3674	1.0839	−0.1872	0.141*
H26B	−0.2886	0.9858	−0.2269	0.141*
C27	−0.2985 (5)	0.9933 (3)	−0.0777 (3)	0.0803 (14)
H27A	−0.1831	0.9935	−0.0616	0.096*
H27B	−0.3274	1.0464	−0.0295	0.096*
C28	−0.3789 (3)	0.8899 (3)	−0.0767 (2)	0.0458 (7)
H28A	−0.3074	0.8366	−0.0830	0.055*
H28B	−0.4138	0.8885	−0.0136	0.055*
C29	−1.6615 (5)	0.2240 (3)	−0.4237 (3)	0.0775 (13)
H29A	−1.7195	0.2535	−0.4808	0.093*
H29B	−1.7253	0.2222	−0.3732	0.093*
C30	−1.5043 (5)	0.2843 (3)	−0.3789 (3)	0.0711 (11)
H30A	−1.4632	0.3152	−0.4305	0.085*
H30B	−1.5113	0.3396	−0.3249	0.085*
C31	−1.6218 (5)	0.1181 (4)	−0.4579 (4)	0.1060 (18)
H31A	−1.6841	0.0651	−0.4344	0.127*
H31B	−1.6424	0.1035	−0.5319	0.127*
C32	−1.4515 (4)	0.1209 (3)	−0.4119 (3)	0.0597 (9)
H32A	−1.4318	0.0597	−0.3792	0.072*
H32B	−1.3903	0.1214	−0.4639	0.072*
O1	−0.5089 (3)	0.8730 (2)	−0.15946 (18)	0.0759 (9)
O2	−1.4060 (3)	0.2116 (2)	−0.3400 (2)	0.0729 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.03099 (14)	0.03448 (16)	0.02975 (14)	0.00822 (11)	0.01185 (10)	−0.00015 (11)
Se2	0.04014 (16)	0.04474 (18)	0.02508 (13)	0.00840 (13)	0.01300 (11)	0.00342 (12)
P1	0.0222 (3)	0.0213 (3)	0.0209 (3)	0.0035 (2)	0.0052 (2)	0.0019 (2)
P2	0.0260 (3)	0.0226 (3)	0.0201 (3)	0.0032 (3)	0.0040 (2)	0.0015 (3)
N1	0.0213 (9)	0.0259 (11)	0.0232 (9)	0.0014 (8)	0.0038 (8)	0.0056 (9)
C1	0.0285 (12)	0.0201 (12)	0.0239 (11)	0.0060 (10)	0.0000 (9)	0.0034 (10)
C2	0.0361 (14)	0.0271 (14)	0.0303 (13)	0.0023 (11)	0.0016 (11)	0.0067 (11)
C3	0.0482 (17)	0.0288 (15)	0.0400 (15)	−0.0067 (13)	−0.0041 (13)	0.0123 (13)
C4	0.067 (2)	0.0203 (14)	0.0343 (15)	−0.0016 (14)	−0.0115 (14)	0.0047 (12)
C5	0.066 (2)	0.0281 (15)	0.0265 (13)	0.0193 (14)	0.0019 (13)	0.0004 (12)
C6	0.0395 (14)	0.0263 (14)	0.0278 (12)	0.0113 (12)	0.0046 (11)	0.0036 (11)
C7	0.0233 (11)	0.0248 (13)	0.0280 (12)	0.0025 (10)	0.0050 (9)	0.0097 (11)
C8	0.0274 (13)	0.0361 (16)	0.0402 (15)	0.0046 (12)	0.0080 (11)	0.0048 (13)
C9	0.0293 (14)	0.0415 (18)	0.069 (2)	0.0093 (13)	0.0080 (14)	0.0145 (17)
C10	0.0288 (14)	0.054 (2)	0.0584 (19)	0.0025 (14)	−0.0038 (14)	0.0304 (17)
C11	0.0404 (16)	0.071 (2)	0.0298 (14)	−0.0061 (16)	−0.0064 (12)	0.0129 (15)
C12	0.0327 (14)	0.0519 (19)	0.0291 (13)	0.0033 (13)	0.0052 (11)	0.0078 (13)
C13	0.0273 (12)	0.0263 (13)	0.0227 (11)	0.0040 (10)	0.0006 (9)	0.0046 (10)
C14	0.0362 (14)	0.0265 (14)	0.0274 (12)	0.0045 (11)	−0.0022 (11)	0.0036 (11)
C15	0.0458 (17)	0.0310 (16)	0.0396 (15)	−0.0063 (13)	−0.0096 (13)	0.0041 (13)
C16	0.0333 (15)	0.051 (2)	0.0488 (17)	−0.0114 (14)	−0.0059 (13)	0.0133 (16)
C17	0.0269 (13)	0.060 (2)	0.0431 (16)	0.0041 (14)	0.0048 (12)	0.0097 (16)
C18	0.0300 (13)	0.0350 (15)	0.0294 (13)	0.0054 (11)	0.0038 (11)	0.0007 (12)
C19	0.0303 (12)	0.0234 (13)	0.0269 (12)	0.0041 (10)	0.0035 (10)	0.0056 (11)
C20	0.0541 (17)	0.0354 (16)	0.0279 (13)	0.0105 (14)	0.0051 (12)	0.0086 (12)
C21	0.086 (2)	0.0343 (17)	0.0415 (16)	0.0198 (17)	0.0089 (16)	0.0167 (15)
C22	0.084 (2)	0.0257 (16)	0.0518 (19)	0.0169 (16)	0.0092 (17)	0.0083 (15)
C23	0.080 (2)	0.0306 (16)	0.0328 (15)	0.0181 (16)	0.0017 (15)	−0.0043 (13)
C24	0.0564 (18)	0.0275 (15)	0.0278 (13)	0.0135 (13)	0.0016 (12)	0.0050 (12)
C25	0.081 (3)	0.115 (4)	0.093 (3)	−0.053 (3)	−0.037 (2)	0.084 (3)
C26	0.181 (5)	0.068 (3)	0.062 (3)	−0.064 (3)	−0.046 (3)	0.032 (2)
C27	0.110 (3)	0.062 (3)	0.0447 (19)	−0.040 (2)	−0.023 (2)	0.0176 (19)
C28	0.0414 (16)	0.052 (2)	0.0389 (15)	−0.0047 (14)	−0.0020 (13)	0.0135 (15)
C29	0.084 (3)	0.083 (3)	0.065 (2)	0.045 (3)	0.002 (2)	0.013 (2)
C30	0.103 (3)	0.043 (2)	0.076 (3)	0.012 (2)	0.031 (2)	0.019 (2)
C31	0.076 (3)	0.086 (3)	0.129 (4)	0.032 (3)	−0.017 (3)	−0.029 (3)
C32	0.066 (2)	0.054 (2)	0.065 (2)	0.0075 (18)	0.0208 (18)	0.0176 (19)
O1	0.0602 (14)	0.0791 (18)	0.0706 (16)	−0.0410 (13)	−0.0293 (12)	0.0512 (15)
O2	0.0687 (17)	0.0558 (16)	0.0827 (19)	−0.0001 (13)	−0.0040 (14)	0.0105 (15)

Geometric parameters (Å, º)

Se1—P1	2.0967 (7)	C17—C18	1.401 (4)
Se2—P2	2.0990 (7)	C17—H17A	0.9500
P1—N1	1.6896 (19)	C18—H18A	0.9500
P1—C1	1.815 (3)	C19—C24	1.388 (3)
P1—C7	1.820 (2)	C19—C20	1.392 (3)
P2—N1	1.6804 (19)	C20—C21	1.389 (4)
P2—C19	1.812 (3)	C20—H20A	0.9500
P2—C13	1.818 (2)	C21—C22	1.382 (4)
N1—O1	2.815 (3)	C21—H21A	0.9500
N1—H1A	0.8800	C22—C23	1.377 (4)
C1—C2	1.390 (4)	C22—H22A	0.9500
C1—C6	1.400 (3)	C23—C24	1.386 (4)
C2—C3	1.390 (4)	C23—H23A	0.9500
C2—H2A	0.9500	C24—H24A	0.9500
C3—C4	1.379 (4)	C25—C26	1.330 (6)
C3—H3A	0.9500	C25—O1	1.451 (4)
C4—C5	1.370 (4)	C25—H25A	0.9900
C4—H4A	0.9500	C25—H25B	0.9900
C5—C6	1.387 (4)	C26—C27	1.515 (4)
C5—H5A	0.9500	C26—H26A	0.9900
C6—H6A	0.9500	C26—H26B	0.9900
C7—C12	1.390 (3)	C27—C28	1.494 (4)
C7—C8	1.389 (3)	C27—H27A	0.9900
C8—C9	1.387 (4)	C27—H27B	0.9900
C8—H8A	0.9500	C28—O1	1.410 (3)
C9—C10	1.370 (4)	C28—H28A	0.9900
C9—H9A	0.9500	C28—H28B	0.9900
C10—C11	1.378 (4)	C29—C30	1.500 (6)
C10—H10A	0.9500	C29—C31	1.511 (6)
C11—C12	1.399 (4)	C29—H29A	0.9900
C11—H11A	0.9500	C29—H29B	0.9900
C12—H12A	0.9500	C30—O2	1.426 (4)
C13—C14	1.388 (4)	C30—H30A	0.9900
C13—C18	1.390 (3)	C30—H30B	0.9900
C14—C15	1.387 (4)	C31—C32	1.489 (5)
C14—H14A	0.9500	C31—H31A	0.9900
C15—C16	1.375 (4)	C31—H31B	0.9900
C15—H15A	0.9500	C32—O2	1.422 (4)
C16—C17	1.384 (4)	C32—H32A	0.9900
C16—H16A	0.9500	C32—H32B	0.9900
N1—P1—C1	104.00 (10)	C17—C18—H18A	120.1
N1—P1—C7	100.91 (10)	C24—C19—C20	119.1 (2)
C1—P1—C7	107.79 (11)	C24—C19—P2	121.09 (18)
N1—P1—Se1	117.36 (7)	C20—C19—P2	119.8 (2)
C1—P1—Se1	113.05 (8)	C21—C20—C19	120.2 (3)
C7—P1—Se1	112.56 (8)	C21—C20—H20A	119.9
N1—P2—C19	105.26 (11)	C19—C20—H20A	119.9
N1—P2—C13	107.57 (10)	C22—C21—C20	119.9 (3)
C19—P2—C13	105.86 (11)	C22—C21—H21A	120.0
N1—P2—Se2	111.96 (7)	C20—C21—H21A	120.0
C19—P2—Se2	112.39 (8)	C23—C22—C21	120.1 (3)
C13—P2—Se2	113.26 (8)	C23—C22—H22A	119.9
P2—N1—P1	132.67 (12)	C21—C22—H22A	119.9
P2—N1—O1	106.87 (10)	C22—C23—C24	120.2 (3)
P1—N1—O1	118.72 (10)	C22—C23—H23A	119.9
P2—N1—H1A	113.7	C24—C23—H23A	119.9
P1—N1—H1A	113.7	C23—C24—C19	120.4 (2)
O1—N1—H1A	16.3	C23—C24—H24A	119.8
C2—C1—C6	119.2 (2)	C19—C24—H24A	119.8
C2—C1—P1	120.04 (19)	C26—C25—O1	109.3 (3)
C6—C1—P1	120.72 (19)	C26—C25—H25A	109.8
C3—C2—C1	120.3 (3)	O1—C25—H25A	109.8
C3—C2—H2A	119.9	C26—C25—H25B	109.8
C1—C2—H2A	119.9	O1—C25—H25B	109.8
C4—C3—C2	120.0 (3)	H25A—C25—H25B	108.3
C4—C3—H3A	120.0	C25—C26—C27	106.3 (4)
C2—C3—H3A	120.0	C25—C26—H26A	110.5
C5—C4—C3	120.1 (3)	C27—C26—H26A	110.5
C5—C4—H4A	120.0	C25—C26—H26B	110.5
C3—C4—H4A	120.0	C27—C26—H26B	110.5
C4—C5—C6	120.9 (3)	H26A—C26—H26B	108.7
C4—C5—H5A	119.5	C28—C27—C26	102.7 (3)
C6—C5—H5A	119.5	C28—C27—H27A	111.2
C5—C6—C1	119.5 (3)	C26—C27—H27A	111.2
C5—C6—H6A	120.3	C28—C27—H27B	111.2
C1—C6—H6A	120.3	C26—C27—H27B	111.2
C12—C7—C8	119.3 (2)	H27A—C27—H27B	109.1
C12—C7—P1	119.74 (19)	O1—C28—C27	105.9 (2)
C8—C7—P1	120.91 (19)	O1—C28—H28A	110.6
C9—C8—C7	120.0 (3)	C27—C28—H28A	110.6
C9—C8—H8A	120.0	O1—C28—H28B	110.6
C7—C8—H8A	120.0	C27—C28—H28B	110.6
C10—C9—C8	120.4 (3)	H28A—C28—H28B	108.7
C10—C9—H9A	119.8	C30—C29—C31	103.6 (3)
C8—C9—H9A	119.8	C30—C29—H29A	111.0
C9—C10—C11	120.5 (3)	C31—C29—H29A	111.0
C9—C10—H10A	119.8	C30—C29—H29B	111.0
C11—C10—H10A	119.8	C31—C29—H29B	111.0
C10—C11—C12	119.7 (3)	H29A—C29—H29B	109.0
C10—C11—H11A	120.2	O2—C30—C29	105.0 (3)
C12—C11—H11A	120.2	O2—C30—H30A	110.7
C7—C12—C11	120.1 (3)	C29—C30—H30A	110.7
C7—C12—H12A	120.0	O2—C30—H30B	110.7
C11—C12—H12A	120.0	C29—C30—H30B	110.7
C14—C13—C18	119.7 (2)	H30A—C30—H30B	108.8
C14—C13—P2	120.02 (19)	C32—C31—C29	104.5 (4)
C18—C13—P2	120.23 (19)	C32—C31—H31A	110.8
C15—C14—C13	120.3 (3)	C29—C31—H31A	110.8
C15—C14—H14A	119.8	C32—C31—H31B	110.8
C13—C14—H14A	119.8	C29—C31—H31B	110.8
C16—C15—C14	119.8 (3)	H31A—C31—H31B	108.9
C16—C15—H15A	120.1	O2—C32—C31	107.7 (3)
C14—C15—H15A	120.1	O2—C32—H32A	110.2
C15—C16—C17	120.9 (3)	C31—C32—H32A	110.2
C15—C16—H16A	119.6	O2—C32—H32B	110.2
C17—C16—H16A	119.6	C31—C32—H32B	110.2
C16—C17—C18	119.4 (3)	H32A—C32—H32B	108.5
C16—C17—H17A	120.3	C28—O1—C25	108.2 (2)
C18—C17—H17A	120.3	C28—O1—N1	132.18 (17)
C13—C18—C17	119.8 (3)	C25—O1—N1	118.12 (18)
C13—C18—H18A	120.1	C32—O2—C30	104.8 (3)
C19—P2—N1—P1	104.35 (18)	N1—P2—C13—C18	83.4 (2)
C13—P2—N1—P1	−8.2 (2)	C19—P2—C13—C18	−28.7 (2)
Se2—P2—N1—P1	−133.26 (14)	Se2—P2—C13—C18	−152.33 (17)
C19—P2—N1—O1	−59.89 (13)	C18—C13—C14—C15	−1.5 (4)
C13—P2—N1—O1	−172.44 (12)	P2—C13—C14—C15	179.90 (19)
Se2—P2—N1—O1	62.51 (11)	C13—C14—C15—C16	1.9 (4)
C1—P1—N1—P2	58.93 (18)	C14—C15—C16—C17	−0.5 (4)
C7—P1—N1—P2	170.57 (17)	C15—C16—C17—C18	−1.2 (4)
Se1—P1—N1—P2	−66.77 (18)	C14—C13—C18—C17	−0.3 (4)
C1—P1—N1—O1	−138.32 (13)	P2—C13—C18—C17	178.37 (19)
C7—P1—N1—O1	−26.68 (15)	C16—C17—C18—C13	1.6 (4)
Se1—P1—N1—O1	95.99 (12)	N1—P2—C19—C24	−17.9 (2)
N1—P1—C1—C2	−144.27 (19)	C13—P2—C19—C24	95.8 (2)
C7—P1—C1—C2	109.2 (2)	Se2—P2—C19—C24	−140.0 (2)
Se1—P1—C1—C2	−15.9 (2)	N1—P2—C19—C20	163.3 (2)
N1—P1—C1—C6	33.8 (2)	C13—P2—C19—C20	−82.9 (2)
C7—P1—C1—C6	−72.7 (2)	Se2—P2—C19—C20	41.2 (2)
Se1—P1—C1—C6	162.22 (16)	C24—C19—C20—C21	−0.6 (4)
C6—C1—C2—C3	−2.0 (4)	P2—C19—C20—C21	178.2 (2)
P1—C1—C2—C3	176.14 (19)	C19—C20—C21—C22	2.0 (5)
C1—C2—C3—C4	0.6 (4)	C20—C21—C22—C23	−1.9 (6)
C2—C3—C4—C5	1.1 (4)	C21—C22—C23—C24	0.4 (6)
C3—C4—C5—C6	−1.3 (4)	C22—C23—C24—C19	0.9 (5)
C4—C5—C6—C1	−0.1 (4)	C20—C19—C24—C23	−0.8 (4)
C2—C1—C6—C5	1.8 (3)	P2—C19—C24—C23	−179.6 (3)
P1—C1—C6—C5	−176.35 (18)	O1—C25—C26—C27	−25.2 (7)
N1—P1—C7—C12	118.7 (2)	C25—C26—C27—C28	27.9 (6)
C1—P1—C7—C12	−132.6 (2)	C26—C27—C28—O1	−19.8 (5)
Se1—P1—C7—C12	−7.2 (2)	C31—C29—C30—O2	−30.7 (5)
N1—P1—C7—C8	−61.4 (2)	C30—C29—C31—C32	11.3 (5)
C1—P1—C7—C8	47.3 (2)	C29—C31—C32—O2	11.9 (5)
Se1—P1—C7—C8	172.69 (17)	C27—C28—O1—C25	6.0 (4)
C12—C7—C8—C9	−0.5 (4)	C27—C28—O1—N1	−159.5 (3)
P1—C7—C8—C9	179.6 (2)	C26—C25—O1—C28	12.5 (6)
C7—C8—C9—C10	0.0 (4)	C26—C25—O1—N1	−179.6 (4)
C8—C9—C10—C11	−0.2 (5)	P2—N1—O1—C28	174.7 (3)
C9—C10—C11—C12	0.9 (5)	P1—N1—O1—C28	7.8 (4)
C8—C7—C12—C11	1.2 (4)	P2—N1—O1—C25	10.3 (4)
P1—C7—C12—C11	−178.9 (2)	P1—N1—O1—C25	−156.6 (3)
C10—C11—C12—C7	−1.4 (4)	C31—C32—O2—C30	−31.8 (4)
N1—P2—C13—C14	−98.0 (2)	C29—C30—O2—C32	38.9 (4)
C19—P2—C13—C14	149.87 (19)	Se1—P1—P2—Se2	179.19 (3)
Se2—P2—C13—C14	26.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	1.99	2.815 (3)	157