Crystal structures of bis-[2-(di-phenyl-phosphino-thio-yl)phen-yl] ether and bis-{2-[diphen-yl(selanyl-idene)phosphan-yl]phen-yl} ether.

The title compounds, C36H28OP2S2, (1), and C36H28OP2Se2, (2), exhibit remarkably similar structures although they are not isomorphous. The whole mol-ecule of compound (2) is generated by twofold symmetry, with the ether O atom located on the twofold axis. Both compounds have intra-molecular π-π inter-actions between terminal phenyl rings with centroid-centroid distances of 3.6214 (16) and 3.8027 (14) Å in (1) and (2), respectively. In the crystal of (1), short C-H⋯S hydrogen bonds link the mol-ecules, forming chains along [001], while in (2) there are no analogous C-H⋯Se inter-actions present.

Chemical context

The ligand bis­[2-(di­phenyl­phosphan­yl)phen­yl] ether (POP) and its congeners, including the more rigid Xantphos [(9,9-dimethyl-9H-xanthene-4,5-di­yl)bis­(di­phenyl­phosphane)], comprise a series of chelating diphosphines with a range of flexibility to accommodate variable bonding geometries at transition metals. Experimental and theoretical studies of metal complexes with diphosphines have shown a strong correlation between diphosphine bite angle and selectivity in catalytic transformations (Dierkes & van Leeuwen, 1999 ▶; Gathy et al., 2011 ▶). Simple functionalization of these diphos­phines to form diphosphine dioxides, di­sulfides, and diselen­ides has permitted further tuning of the bonding of these ligands to metals by changing the bite-angle range as well as the electronic properties of these ligands. The π-accepting phospho­rous donor atoms of the parent diphosphines are profoundly altered with the addition of π-donor chalcogen donor atoms (Dairiki et al., 2009 ▶). Chalcogen-modified diphosphine ligands have been utilized in strategies to tune the catalytic behavior of systems including the PdII-catalysed hydro­amination of dienes (Jahromi et al., 2012 ▶) and RuII transfer hydrogenation of aldehydes and ketones (Deb et al., 2010 ▶). Hemilability, implicated in the selectivity and reactivity of some catalytic reactions (Braunstein et al., 2001 ▶), can also result from the chalcogen functionalization of phosphines as well (Deb et al., 2010 ▶).

Our inter­est in the application of chalcogen-substituted diphosphines to alter the electronic features of photoluminescent CuI sensor materials (Smith et al., 2010 ▶) led us to study the solid-state structural features of the dichalcogen diphosphines, including the di­sulfide and diselenide of the ligand POP. We wanted to investigate the inter- and intra­molecular features that dominate the solid-state structural behavior of these ligands. The mol­ecular geometry and packing of these chalcogen diphosphines may strongly influence the geometric features of their d 10 metal complexes, as d 10 metals typically have poor stereochemical preferences. In this study, the structures obtained for bis­[2-(di­phenyl­phosphino­thio­yl)phen­yl] ether, (1), and bis­{2-[diphen­yl(selanyl­idene)phosphan­yl]phen­yl} ether, (2), are compared.

Structural commentary

The mol­ecular structures of (1) and (2) are illustrated in Figs. 1 ▶ and 2 ▶, respectively. The P—S [1.9543 (8) and 1.9552 (9) Å] and P—Se [2.1125 (6) Å] bond lengths are consistent with covalent radii predictions as well as typical bond lengths for di­aryl­phosphine sulfides and selenides. Although these structures are not isomorphous, many intra­molecular features are remarkably alike despite the potentially flexible ether linkage of the diphosphine backbone. To demonstrate the similarity, several metrics were compared. The intra­molecular P⋯P distances [5.6452 (8) Å for (1); 5.669 (1) Å for (2)], the intra­molecular E⋯E distances [E = S 6.636 (1) Å for (1); E = Se 6.8246 (7) Å for (2)], and the EP⋯PE angles [158.29 (4)° for (1); 158.44 (2)° for (2)] all indicate a common geometry near the phospho­rous–chalcogen bonds. This similarity extends to the phenyl ring orientations. A structural overlap calculation of the pairwise atomic coordinates of all related atoms of (1) and (2) (except the chalcogens) reveals an r.m.s. deviation of only 0.214 Å over 39 atom pairs (Fig. 3 ▶).

Figure 1

The mol­ecular structure of (1), showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

Figure 2

The mol­ecular structure of (2), showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. [Symmetry code: (i) −x, y, −z + .]

Figure 3

Structural overlay of (1) (red) and (2) (blue).

The largest differences in the intra­molecular features of (1) and (2) can be found in the closest approach of a pair of terminal phenyl rings, each bonded to different phospho­rous atoms (Fig. 4 ▶). In the structure of (2), the angle between mean planes formed by atoms C1–C6 and the twofold axis-related atoms C1–C6 of the same mol­ecule is 0.98 (12)°, with a centroid–centroid distance of 3.8027 (14) Å. The analogous relationship in the structure of (1), involving phenyl rings C1–C6 and C31–C36, is a dihedral angle of 6.52 (13)° and a centroid–centroid distance of 3.6214 (16) Å. The result of these differences is that in (2) there is only one C⋯C intra­molecular contact between these phenyl rings shorter than 3.6 Å, while in (1) there are six unique contacts that meet this criteria. Although these intra­molecular C⋯C contacts are slightly longer than the van der Waals radii sum of 3.4 Å, the additional C⋯C close-contacts in (1) may contribute to stronger intra­molecular π–π inter­actions between these phenyl rings compared to (2). The dihedral angles between the mean planes formed by the ether-linked phenyl groups [(C13–C18 and C19–C24) 76.83 (11)° for (1); (C13–C18 and the symmetry-related C13–C18 ring) 84.53 (11)° for (2)] also show a significant difference in the twist around the ether linkage.

Figure 4

Intra­molecular π–π inter­actions in (1) and (2).

Supra­molecular features

The inter­molecular features of (1) and (2) reveal additional differences between these seemingly similar structures. In the crystal of (1), most notably there are three unique inter­molecular C—H⋯S inter­actions (Table 1 ▶) shorter than the sum of the van der Waals radii. Each mol­ecule participates as a C—H donor with two different S2 acceptors as well as one S1 acceptor (Table 1 ▶ and Fig. 5 ▶). As such, each mol­ecule is involved in C—H⋯S inter­molecular inter­actions with three other unique mol­ecules. In the crystal of (2), no analogous C—H⋯Se inter­molecular inter­actions are present.

Table 1

Hydrogen-bond geometry (, ) for (1)

Cg4 is the centroid of ring C19C24.

DHA	DH	HA	D A	DHA
C11H11S2i	0.95	2.82	3.696(2)	153
C4H4S2ii	0.95	2.94	3.698(3)	138
C5H5S1iii	0.95	2.93	3.796(3)	152
C9H9Cg4iv	0.95	2.94	3.598(3)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Figure 5

Inter­molecular C—H⋯S inter­actions in (1). [Symmetry codes: (i) x + , −y + , −z + 1; (ii) x, −y + , z + .]

Both structures show that several inter­molecular C—H⋯π contacts less than ca 3.0 Å are present but these are likely to play a weak role in packing inter­actions [see Table 1 ▶ for (1) and Table 2 ▶ for (2)]. Mol­ecules of (1) stack in columns parallel to [010] (Fig. 6 ▶). The intra­molecular π–π stacking inter­actions of (1) are all aligned perpendicular to the column stacking axis. Mol­ecules of (2) stack in columns parallel to [101] (Fig. 7 ▶) with intra­molecular π–π stacking perpendicular to the column stacking vector.

Table 2

Hydrogen-bond geometry (, ) for (2)

Cg2 and Cg3 are the centroids of rings C7C12 and C13C18, respectively.

DHA	DH	HA	D A	DHA
C5H5Cg2i	0.95	2.63	3.546(3)	161
C9H9Cg3ii	0.95	2.94	3.676(3)	135

Symmetry codes: (i) ; (ii) .

Figure 6

Crystal packing of (1), viewed along [010] (above) and [100] (below). Color to highlight mol­ecules packing within columns.

Figure 7

Crystal packing of (2) viewed along [101] (above) and [010] (below). Color to highlight mol­ecules packing within columns.

Database survey

The Cambridge Structural Database (Version 5.35; Groom & Allen, 2014 ▶) contains several closely related phosphine sulfide structures, including Xantphos di­sulfide (Jahromi et al., 2012 ▶), POP mono­sulfide (Deb et al., 2010 ▶), and POP dioxide (Deb & Dutta, 2010 ▶). As the xanthene backbone of the diphosphine linkage is more sterically constrained compared with the ether linkage of POP, the Xantphos di­sulfide structure forces the intra­molecular S⋯S [4.207 (1) Å] and P⋯P [4.984 (1) Å] distances to be much shorter compared with (1). The structure of POP mono­sulfide is also very different from (1), as intra­molecular phenyl ring inter­actions are present but these involve a terminal phenyl ring and a bridging phenyl ring rather than two terminal phenyl rings as in (1). POP dioxide adopts a conformation unlike (1) or (2), as the P—O bond vectors are closer to anti­parallel [intra­molecular OP⋯P—O angles of 37.0 (6)°]. Considering metal complexes of related ligands, the structures of only two ruthenium(II) complexes (Deb et al., 2010 ▶), three palladium(II) complexes (Milheiro & Faller, 2011 ▶; Saikia et al., 2012 ▶), and one rhodium(I) complex (Faller et al., 2008 ▶) have been reported with Xantphos sulfide or POP sulfide. The structure of only one palladium(II) complex of Xantphos di­sulfide (Jahromi et al., 2012 ▶) is reported. POP or Xantphos selenide structures are even rarer, as only one copper(I) complex of POP selenide is reported (Venkateswaran et al., 2007b ▶). No structures to date have been reported with diselenides of POP or Xantphos.

Synthesis and crystallization

Compounds (1) and (2) were prepared using a reported procedure (Venkateswaran et al., 2007a ▶). Crystals of each sample were obtained by diffusion of diethyl ether into a concentrated di­chloro­methane solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3 ▶. H atoms were placed in calculated positions and refined in the riding-model approximation: C—H = 0.95 Å with U(H) = 1.2U(C).

Table 3

Experimental details

	(1)	(2)
Crystal data
Chemical formula	C36H28OP2S2	C36H28OP2Se2
M r	602.64	696.44
Crystal system, space group	Orthorhombic, P b c a	Monoclinic, C2/c
Temperature (K)	173	173
a, b, c ()	14.1161(9), 18.0874(12), 23.1986(16)	14.0964(15), 13.0854(13), 17.5918(18)
, , ()	90, 90, 90	90, 109.226(8), 90
V (3)	5923.1(7)	3064.0(6)
Z	8	4
Radiation type	Mo K	Mo K
(mm1)	0.32	2.55
Crystal size (mm)	0.52 0.24 0.12	0.80 0.12 0.12
Data collection
Diffractometer	Rigaku XtaLAB mini	Rigaku XtaLAB mini
Absorption correction	Multi-scan (REQAB; Rigaku, 1998 ▶)	Multi-scan (REQAB; Rigaku, 1998 ▶)
T min, T max	0.718, 0.963	0.556, 0.737
No. of measured, independent and observed [I > 2(I)] reflections	54343, 6050, 4671	15840, 3521, 2958
R int	0.073	0.045
(sin /)max (1)	0.625	0.649
Refinement
R[F 2 > 2(F 2)], wR(F 2), S	0.045, 0.101, 1.07	0.032, 0.066, 1.07
No. of reflections	6050	3521
No. of parameters	370	186
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
max, min (e 3)	0.37, 0.33	0.40, 0.41

Computer programs: CrystalClear-SM Expert (Rigaku Americas and Rigaku, 2011 ▶), SIR2004 (Burla et al., 2005 ▶), SHELXL2013 (Sheldrick, 2008 ▶), ORTEP-3 for Windows (Farrugia, 2012 ▶) and CrystalStructure (Rigaku, 2010 ▶).

A small number of low-angle reflections [nine for (1) and five for (2)] were missing from these high-quality data sets due to the arrangement of the instrument with a conservatively sized beam stop and a fixed-position detector. The large number of reflections in the data sets (and the Fourier-transform relationship of intensities to atoms) ensures that no particular bias was thereby introduced into this routine structure determination.

Crystal structure: contains datablock(s) 1, 2, general. DOI: 10.1107/S1600536814023988/su5010sup1.cif

Structure factors: contains datablock(s) 1. DOI: 10.1107/S1600536814023988/su50101sup2.hkl

Structure factors: contains datablock(s) 2. DOI: 10.1107/S1600536814023988/su50102sup3.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814023988/su50101sup4.cml

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814023988/su50102sup5.cml

CCDC references: 1031850, 1031849

Additional supporting information: crystallographic information; 3D view; checkCIF report

C36H28OP2Se2	F(000) = 1400
Mr = 696.44	Dx = 1.510 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71075 Å
a = 14.0964 (15) Å	Cell parameters from 13788 reflections
b = 13.0854 (13) Å	θ = 3.1–27.6°
c = 17.5918 (18) Å	µ = 2.55 mm−1
β = 109.226 (8)°	T = 173 K
V = 3064.0 (6) Å3	Prism, colorless
Z = 4	0.80 × 0.12 × 0.12 mm

Rigaku XtaLAB mini diffractometer	3521 independent reflections
Radiation source: normal-focus sealed tube	2958 reflections with I > 2σ(I)
Detector resolution: 6.849 pixels mm-1	Rint = 0.045
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −18→18
Tmin = 0.556, Tmax = 0.737	k = −16→16
15840 measured reflections	l = −22→22

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.066	w = 1/[σ2(Fo2) + (0.0183P)2 + 4.7666P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3521 reflections	Δρmax = 0.40 e Å−3
186 parameters	Δρmin = −0.41 e Å−3

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.

	x	y	z	Uiso*/Ueq
Se1	0.15497 (2)	0.31054 (2)	0.63637 (2)	0.02846 (8)
P1	−0.00071 (4)	0.28040 (4)	0.58870 (3)	0.01801 (12)
O1	0.0000	0.35271 (16)	0.7500	0.0191 (4)
C1	−0.03973 (16)	0.15982 (16)	0.61952 (12)	0.0201 (5)
C2	−0.10828 (17)	0.15221 (18)	0.66065 (14)	0.0267 (5)
H2	−0.1341	0.2123	0.6770	0.032*
C3	−0.13892 (19)	0.0569 (2)	0.67788 (15)	0.0336 (6)
H3	−0.1859	0.0521	0.7060	0.040*
C4	−0.10223 (19)	−0.03063 (19)	0.65480 (15)	0.0338 (6)
H4	−0.1242	−0.0956	0.6665	0.041*
C5	−0.0331 (2)	−0.02409 (19)	0.61439 (15)	0.0333 (6)
H5	−0.0075	−0.0846	0.5985	0.040*
C6	−0.00137 (18)	0.07029 (18)	0.59724 (14)	0.0284 (5)
H6	0.0468	0.0745	0.5702	0.034*
C7	−0.04357 (15)	0.27085 (16)	0.47944 (12)	0.0189 (4)
C8	−0.13290 (16)	0.22060 (18)	0.43821 (13)	0.0238 (5)
H8	−0.1715	0.1900	0.4673	0.029*
C9	−0.16556 (16)	0.21505 (18)	0.35504 (14)	0.0264 (5)
H9	−0.2261	0.1801	0.3272	0.032*
C10	−0.11013 (18)	0.26041 (18)	0.31268 (14)	0.0276 (5)
H10	−0.1332	0.2576	0.2555	0.033*
C11	−0.02133 (19)	0.30990 (19)	0.35299 (14)	0.0312 (6)
H11	0.0168	0.3407	0.3235	0.037*
C12	0.01247 (17)	0.31487 (18)	0.43633 (13)	0.0255 (5)
H12	0.0740	0.3484	0.4639	0.031*
C13	−0.07964 (15)	0.37932 (16)	0.60936 (12)	0.0191 (4)
C14	−0.15170 (16)	0.43227 (17)	0.54724 (14)	0.0237 (5)
H14	−0.1613	0.4148	0.4928	0.028*
C15	−0.20897 (16)	0.50950 (17)	0.56408 (15)	0.0269 (5)
H15	−0.2571	0.5447	0.5213	0.032*
C16	−0.19615 (16)	0.53555 (17)	0.64311 (15)	0.0267 (5)
H16	−0.2361	0.5880	0.6545	0.032*
C17	−0.12510 (16)	0.48518 (17)	0.70579 (14)	0.0227 (5)
H17	−0.1160	0.5031	0.7601	0.027*
C18	−0.06746 (15)	0.40848 (16)	0.68848 (13)	0.0188 (4)

	U11	U22	U33	U12	U13	U23
Se1	0.01582 (11)	0.04058 (16)	0.02624 (13)	−0.00167 (10)	0.00320 (9)	−0.00400 (11)
P1	0.0159 (3)	0.0209 (3)	0.0167 (3)	−0.0006 (2)	0.0045 (2)	0.0003 (2)
O1	0.0205 (10)	0.0157 (10)	0.0196 (10)	0.000	0.0047 (9)	0.000
C1	0.0214 (11)	0.0192 (11)	0.0178 (10)	0.0017 (8)	0.0037 (9)	0.0022 (8)
C2	0.0281 (12)	0.0227 (12)	0.0325 (13)	−0.0018 (9)	0.0142 (11)	−0.0006 (10)
C3	0.0355 (14)	0.0317 (15)	0.0396 (15)	−0.0068 (11)	0.0202 (12)	0.0012 (11)
C4	0.0409 (14)	0.0209 (13)	0.0363 (14)	−0.0047 (11)	0.0084 (12)	0.0064 (10)
C5	0.0453 (15)	0.0202 (13)	0.0329 (13)	0.0092 (11)	0.0108 (12)	0.0022 (10)
C6	0.0312 (13)	0.0279 (13)	0.0281 (12)	0.0063 (10)	0.0126 (10)	0.0038 (10)
C7	0.0194 (10)	0.0193 (11)	0.0172 (10)	−0.0004 (8)	0.0047 (8)	0.0005 (8)
C8	0.0191 (11)	0.0285 (13)	0.0233 (11)	−0.0044 (9)	0.0064 (9)	−0.0018 (9)
C9	0.0192 (11)	0.0282 (13)	0.0272 (12)	−0.0004 (9)	0.0013 (9)	−0.0034 (10)
C10	0.0347 (13)	0.0273 (13)	0.0178 (11)	0.0008 (10)	0.0047 (10)	0.0019 (9)
C11	0.0386 (14)	0.0326 (14)	0.0244 (12)	−0.0083 (11)	0.0129 (11)	0.0066 (10)
C12	0.0253 (11)	0.0257 (12)	0.0246 (11)	−0.0089 (10)	0.0071 (9)	0.0002 (10)
C13	0.0170 (10)	0.0166 (11)	0.0225 (11)	−0.0018 (8)	0.0049 (9)	0.0009 (9)
C14	0.0208 (11)	0.0234 (12)	0.0240 (11)	−0.0027 (9)	0.0035 (9)	0.0032 (9)
C15	0.0191 (11)	0.0208 (12)	0.0353 (13)	0.0007 (9)	0.0018 (10)	0.0059 (10)
C16	0.0199 (11)	0.0184 (12)	0.0411 (14)	0.0014 (9)	0.0091 (10)	−0.0010 (10)
C17	0.0215 (11)	0.0192 (11)	0.0282 (12)	−0.0038 (9)	0.0090 (10)	−0.0029 (9)
C18	0.0167 (10)	0.0161 (11)	0.0232 (11)	−0.0028 (8)	0.0058 (9)	0.0027 (8)

Se1—P1	2.1125 (6)	C8—C9	1.384 (3)
P1—C1	1.812 (2)	C8—H8	0.9500
P1—C7	1.819 (2)	C9—C10	1.379 (3)
P1—C13	1.820 (2)	C9—H9	0.9500
O1—C18	1.389 (2)	C10—C11	1.380 (3)
O1—C18i	1.389 (2)	C10—H10	0.9500
C1—C2	1.388 (3)	C11—C12	1.386 (3)
C1—C6	1.399 (3)	C11—H11	0.9500
C2—C3	1.385 (3)	C12—H12	0.9500
C2—H2	0.9500	C13—C18	1.398 (3)
C3—C4	1.372 (4)	C13—C14	1.405 (3)
C3—H3	0.9500	C14—C15	1.385 (3)
C4—C5	1.385 (4)	C14—H14	0.9500
C4—H4	0.9500	C15—C16	1.384 (3)
C5—C6	1.380 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.388 (3)
C6—H6	0.9500	C16—H16	0.9500
C7—C12	1.387 (3)	C17—C18	1.387 (3)
C7—C8	1.394 (3)	C17—H17	0.9500
C1—P1—C7	103.20 (10)	C10—C9—C8	119.9 (2)
C1—P1—C13	107.09 (10)	C10—C9—H9	120.1
C7—P1—C13	104.34 (10)	C8—C9—H9	120.1
C1—P1—Se1	114.95 (7)	C9—C10—C11	120.2 (2)
C7—P1—Se1	111.86 (7)	C9—C10—H10	119.9
C13—P1—Se1	114.30 (7)	C11—C10—H10	119.9
C18—O1—C18i	116.6 (2)	C10—C11—C12	120.2 (2)
C2—C1—C6	119.0 (2)	C10—C11—H11	119.9
C2—C1—P1	123.39 (17)	C12—C11—H11	119.9
C6—C1—P1	117.51 (17)	C11—C12—C7	120.0 (2)
C3—C2—C1	119.9 (2)	C11—C12—H12	120.0
C3—C2—H2	120.0	C7—C12—H12	120.0
C1—C2—H2	120.0	C18—C13—C14	117.4 (2)
C4—C3—C2	120.8 (2)	C18—C13—P1	120.67 (16)
C4—C3—H3	119.6	C14—C13—P1	121.89 (17)
C2—C3—H3	119.6	C15—C14—C13	121.1 (2)
C3—C4—C5	119.8 (2)	C15—C14—H14	119.5
C3—C4—H4	120.1	C13—C14—H14	119.5
C5—C4—H4	120.1	C16—C15—C14	120.1 (2)
C6—C5—C4	120.1 (2)	C16—C15—H15	119.9
C6—C5—H5	120.0	C14—C15—H15	119.9
C4—C5—H5	120.0	C15—C16—C17	120.2 (2)
C5—C6—C1	120.3 (2)	C15—C16—H16	119.9
C5—C6—H6	119.8	C17—C16—H16	119.9
C1—C6—H6	119.8	C18—C17—C16	119.4 (2)
C12—C7—C8	119.4 (2)	C18—C17—H17	120.3
C12—C7—P1	119.88 (16)	C16—C17—H17	120.3
C8—C7—P1	120.72 (16)	C17—C18—O1	120.62 (19)
C9—C8—C7	120.3 (2)	C17—C18—C13	121.83 (19)
C9—C8—H8	119.9	O1—C18—C13	117.40 (18)
C7—C8—H8	119.9
C7—P1—C1—C2	−117.40 (19)	C9—C10—C11—C12	−0.4 (4)
C13—P1—C1—C2	−7.6 (2)	C10—C11—C12—C7	−0.6 (4)
Se1—P1—C1—C2	120.53 (18)	C8—C7—C12—C11	1.0 (4)
C7—P1—C1—C6	59.79 (19)	P1—C7—C12—C11	−178.38 (19)
C13—P1—C1—C6	169.57 (17)	C1—P1—C13—C18	71.55 (19)
Se1—P1—C1—C6	−62.27 (18)	C7—P1—C13—C18	−179.48 (17)
C6—C1—C2—C3	−1.0 (3)	Se1—P1—C13—C18	−57.00 (18)
P1—C1—C2—C3	176.11 (18)	C1—P1—C13—C14	−111.23 (18)
C1—C2—C3—C4	0.1 (4)	C7—P1—C13—C14	−2.2 (2)
C2—C3—C4—C5	0.5 (4)	Se1—P1—C13—C14	120.23 (16)
C3—C4—C5—C6	−0.1 (4)	C18—C13—C14—C15	−0.7 (3)
C4—C5—C6—C1	−0.9 (4)	P1—C13—C14—C15	−177.99 (17)
C2—C1—C6—C5	1.5 (3)	C13—C14—C15—C16	−0.3 (3)
P1—C1—C6—C5	−175.86 (18)	C14—C15—C16—C17	0.7 (3)
C1—P1—C7—C12	−145.39 (19)	C15—C16—C17—C18	−0.2 (3)
C13—P1—C7—C12	102.79 (19)	C16—C17—C18—O1	−176.18 (19)
Se1—P1—C7—C12	−21.3 (2)	C16—C17—C18—C13	−0.8 (3)
C1—P1—C7—C8	35.3 (2)	C18i—O1—C18—C17	−51.46 (16)
C13—P1—C7—C8	−76.5 (2)	C18i—O1—C18—C13	132.9 (2)
Se1—P1—C7—C8	159.41 (16)	C14—C13—C18—C17	1.2 (3)
C12—C7—C8—C9	−0.3 (3)	P1—C13—C18—C17	178.56 (16)
P1—C7—C8—C9	179.05 (17)	C14—C13—C18—O1	176.74 (17)
C7—C8—C9—C10	−0.7 (3)	P1—C13—C18—O1	−5.9 (3)
C8—C9—C10—C11	1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg2ii	0.95	2.63	3.546 (3)	161
C9—H9···Cg3iii	0.95	2.94	3.676 (3)	135