Steric and electronic evaluations of P(o-tol)R₂, where R is phenyl or cyclohexyl: crystal structures of SeP(o-tol)R₂

The crystal structures of SeP(o-tol)R₂, where o-tol is ortho-tolyl (2-methyl­phen­yl) and R is Ph (phen­yl), namely (2-methyl­phen­yl)di­phenyl­phosphane selenide, C₁₉H₁₇PSe, or Cy (cyclo­hex­yl), namely di­cyclo­hex­yl(2-methyl­phen­yl)phosphane selenide, C₁₉H₂₉PSe, were determined to aid in the evaluation of the steric and electronic behaviour of these analogous phosphane com­pounds. The com­pounds crystallized in similar monoclinic crystal systems, but are differentiated in their unit cells by a doubling of the number of independent mol­ecules for R = Cy (Z′ = 2) and the choice of glide plane by convention. The preferred orientation for the o-tolyl substituent obtained from the X-ray structural analysis is gauche for R = Ph and anti for R = Cy (using the Se—P—C_ipso—C_ortho torsion angles as reference). Density functional theory (DFT) calculations showed both conformations to be equally probable and indicate that the preferred solid-state conformer is probably due to the minimization of repulsion energies, resulting in a packing arrangement primarily featuring weak C—H...Se inter­actions and additional C—H...π inter­actions in the R = Ph structure. A detailed electronic and steric analysis was conducted on both phosphanes using Se—P bond lengths, multinuclear NMR ¹J_Se–P coupling constants, theoretical topological evaluation and crystallographic and solid-angle calculations, and compared to selected literature examples. The results indicate that the use of the o-tolyl substituent increases both the electron-donating capability and the steric size, but is also dependent on whether the o-tolyl group adopts a gauche or anti conformation. The single-crystal geometrical data are unable to detect electronic differences between these two structures due to the somewhat large displacement parameters observed for the Se atom in the R = Cy structure.

Computing details

For both structures, data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010) and WinGX (Farrugia, 1999).

(2-Methylphenyl)diphenylphosphane selenide (mo_13hp_wd1_0m)

Crystal data

C19H17PSe	F(000) = 720
Mr = 355.26	Dx = 1.479 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2817 reflections
a = 10.0436 (9) Å	θ = 2.4–26.2°
b = 9.7907 (10) Å	µ = 2.44 mm^−1
c = 16.4825 (17) Å	T = 100 K
β = 100.228 (2)°	Cuboid, colourless
V = 1595.0 (3) Å^3	0.28 × 0.25 × 0.11 mm
Z = 4

Data collection

Bruker APEX DUO 4K CCD diffractometer	3966 independent reflections
Radiation source: sealed tube	3074 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 8.4 pixels mm^-1	θmax = 28.3°, θmin = 2.2°
φ and ω scans	h = −13→11
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −13→13
Tmin = 0.668, Tmax = 0.746	l = −20→21
17497 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0348P)^2 + 0.4172P] where P = (Fo^2 + 2Fc^2)/3
3966 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.72 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 20 s/frame. A total of 1176 frames were collected with a frame width of 0.5° covering up to θ = 28.34° with 99.8% completeness accomplished.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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-ray diffraction experiments for compounds I and II were performed at 100 K with a Bruker APEX DUO diffractometer with Mo-Kα radiation (λ = 0.71073). Data collections were performed with a CCD detector using Apex2 software (Bruker, 2011) from a single crystal mounted on a glass fibre. The intensities were integrated from several series of exposures measuring 0.5° in ω or φ (Bruker, 2008). Absorption corrections based on equivalent reflections were applied by using SADABS (Bruker, 2008). The structures were solved by using SIR97 (Altomare et al., 1999) and refined against all Fo² data.

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

	x	y	z	Uiso*/Ueq
Se1	0.39492 (3)	0.68778 (3)	0.112605 (16)	0.01976 (8)
P1	0.53742 (6)	0.54638 (6)	0.17474 (4)	0.01372 (14)
C1	0.7014 (2)	0.5658 (2)	0.14359 (15)	0.0144 (5)
C2	0.7072 (3)	0.5951 (2)	0.06130 (15)	0.0183 (5)
H2	0.6258	0.6048	0.0224	0.022*
C3	0.8314 (3)	0.6102 (3)	0.03584 (16)	0.0206 (5)
H3	0.8346	0.6281	−0.0204	0.025*
C4	0.9506 (3)	0.5992 (2)	0.09300 (16)	0.0207 (5)
H4	1.0354	0.6111	0.0761	0.025*
C5	0.9454 (3)	0.5707 (2)	0.17488 (16)	0.0191 (5)
H5	1.0271	0.5635	0.2138	0.023*
C6	0.8225 (2)	0.5527 (2)	0.20040 (15)	0.0169 (5)
H6	0.8202	0.5314	0.2564	0.02*
C7	0.5712 (2)	0.5672 (2)	0.28618 (15)	0.0153 (5)
C8	0.5621 (2)	0.6975 (2)	0.31901 (15)	0.0163 (5)
H8	0.5369	0.7728	0.2832	0.02*
C9	0.5899 (2)	0.7177 (3)	0.40405 (16)	0.0199 (5)
H9	0.5846	0.8068	0.4261	0.024*
C10	0.6253 (3)	0.6077 (3)	0.45645 (16)	0.0209 (6)
H10	0.643	0.6212	0.5144	0.025*
C11	0.6349 (3)	0.4772 (3)	0.42407 (16)	0.0242 (6)
H11	0.6596	0.402	0.46	0.029*
C12	0.6085 (3)	0.4571 (3)	0.33947 (16)	0.0208 (5)
H12	0.6158	0.3682	0.3176	0.025*
C13	0.4868 (2)	0.3691 (2)	0.15468 (14)	0.0133 (5)
C14	0.3646 (2)	0.3182 (2)	0.17546 (15)	0.0174 (5)
C15	0.3254 (3)	0.1858 (3)	0.15052 (16)	0.0205 (5)
H15	0.2427	0.1511	0.1625	0.025*
C16	0.4030 (3)	0.1028 (3)	0.10881 (16)	0.0213 (5)
H16	0.3742	0.0125	0.0934	0.026*
C17	0.5227 (3)	0.1531 (2)	0.09000 (15)	0.0194 (5)
H17	0.5766	0.097	0.0617	0.023*
C18	0.5642 (2)	0.2851 (2)	0.11237 (15)	0.0166 (5)
H18	0.6462	0.3189	0.0988	0.02*
C19	0.2782 (3)	0.3993 (3)	0.22372 (18)	0.0261 (6)
H19A	0.1951	0.3484	0.2266	0.039*
H19B	0.255	0.4872	0.1964	0.039*
H19C	0.3281	0.4151	0.2796	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.01963 (14)	0.01717 (13)	0.02205 (14)	0.00645 (10)	0.00256 (10)	0.00325 (11)
P1	0.0138 (3)	0.0120 (3)	0.0152 (3)	0.0010 (2)	0.0021 (2)	−0.0002 (2)
C1	0.0132 (12)	0.0115 (11)	0.0188 (12)	0.0005 (9)	0.0034 (10)	0.0000 (9)
C2	0.0159 (13)	0.0199 (13)	0.0184 (13)	0.0010 (10)	0.0010 (10)	0.0023 (10)
C3	0.0227 (14)	0.0204 (13)	0.0197 (13)	0.0003 (10)	0.0068 (11)	0.0030 (10)
C4	0.0187 (13)	0.0168 (12)	0.0290 (15)	−0.0017 (10)	0.0107 (11)	−0.0026 (11)
C5	0.0153 (13)	0.0180 (12)	0.0224 (13)	0.0017 (10)	−0.0007 (10)	−0.0050 (10)
C6	0.0201 (13)	0.0174 (12)	0.0132 (12)	0.0016 (10)	0.0029 (10)	−0.0020 (10)
C7	0.0123 (12)	0.0166 (12)	0.0175 (12)	−0.0011 (9)	0.0040 (10)	−0.0025 (10)
C8	0.0140 (12)	0.0136 (11)	0.0224 (13)	0.0002 (9)	0.0055 (10)	0.0001 (10)
C9	0.0177 (13)	0.0192 (13)	0.0239 (14)	0.0000 (10)	0.0067 (11)	−0.0075 (10)
C10	0.0219 (14)	0.0260 (14)	0.0160 (12)	−0.0049 (10)	0.0067 (11)	−0.0048 (11)
C11	0.0306 (16)	0.0202 (13)	0.0215 (14)	−0.0043 (11)	0.0034 (12)	0.0036 (11)
C12	0.0292 (15)	0.0129 (12)	0.0202 (13)	0.0002 (10)	0.0045 (11)	−0.0002 (10)
C13	0.0141 (12)	0.0126 (11)	0.0121 (11)	0.0007 (9)	−0.0004 (9)	0.0010 (9)
C14	0.0169 (12)	0.0163 (12)	0.0184 (12)	0.0016 (10)	0.0014 (10)	0.0029 (10)
C15	0.0159 (12)	0.0196 (12)	0.0237 (13)	−0.0032 (10)	−0.0031 (10)	0.0061 (11)
C16	0.0238 (14)	0.0184 (12)	0.0191 (13)	−0.0019 (10)	−0.0036 (11)	0.0009 (11)
C17	0.0238 (14)	0.0164 (12)	0.0169 (12)	0.0053 (10)	0.0004 (10)	0.0006 (10)
C18	0.0152 (12)	0.0176 (12)	0.0157 (12)	0.0015 (9)	−0.0011 (10)	0.0017 (9)
C19	0.0199 (14)	0.0249 (14)	0.0369 (17)	−0.0009 (11)	0.0143 (12)	0.0002 (12)

Geometric parameters (Å, º)

Se1—P1	2.1197 (7)	C9—H9	0.95
P1—C7	1.819 (2)	C10—C11	1.395 (4)
P1—C1	1.820 (2)	C10—H10	0.95
P1—C13	1.823 (2)	C11—C12	1.386 (4)
C1—C2	1.398 (3)	C11—H11	0.95
C1—C6	1.403 (3)	C12—H12	0.95
C2—C3	1.392 (4)	C13—C18	1.400 (3)
C2—H2	0.95	C13—C14	1.422 (3)
C3—C4	1.390 (4)	C14—C15	1.395 (3)
C3—H3	0.95	C14—C19	1.504 (3)
C4—C5	1.388 (4)	C15—C16	1.389 (4)
C4—H4	0.95	C15—H15	0.95
C5—C6	1.384 (3)	C16—C17	1.384 (4)
C5—H5	0.95	C16—H16	0.95
C6—H6	0.95	C17—C18	1.388 (3)
C7—C8	1.394 (3)	C17—H17	0.95
C7—C12	1.399 (3)	C18—H18	0.95
C8—C9	1.394 (3)	C19—H19A	0.98
C8—H8	0.95	C19—H19B	0.98
C9—C10	1.387 (4)	C19—H19C	0.98
C7—P1—C1	104.92 (11)	C9—C10—C11	120.0 (2)
C7—P1—C13	106.61 (11)	C9—C10—H10	120
C1—P1—C13	106.60 (11)	C11—C10—H10	120
C7—P1—Se1	113.79 (8)	C12—C11—C10	120.1 (2)
C1—P1—Se1	111.26 (8)	C12—C11—H11	120
C13—P1—Se1	113.06 (8)	C10—C11—H11	120
C2—C1—C6	119.1 (2)	C11—C12—C7	120.3 (2)
C2—C1—P1	119.40 (18)	C11—C12—H12	119.9
C6—C1—P1	121.51 (18)	C7—C12—H12	119.9
C3—C2—C1	120.5 (2)	C18—C13—C14	119.6 (2)
C3—C2—H2	119.7	C18—C13—P1	119.19 (18)
C1—C2—H2	119.7	C14—C13—P1	121.01 (18)
C4—C3—C2	119.8 (2)	C15—C14—C13	117.7 (2)
C4—C3—H3	120.1	C15—C14—C19	119.2 (2)
C2—C3—H3	120.1	C13—C14—C19	123.1 (2)
C5—C4—C3	119.9 (2)	C16—C15—C14	122.4 (2)
C5—C4—H4	120.1	C16—C15—H15	118.8
C3—C4—H4	120.1	C14—C15—H15	118.8
C6—C5—C4	120.7 (2)	C17—C16—C15	119.2 (2)
C6—C5—H5	119.7	C17—C16—H16	120.4
C4—C5—H5	119.7	C15—C16—H16	120.4
C5—C6—C1	120.0 (2)	C16—C17—C18	120.3 (2)
C5—C6—H6	120	C16—C17—H17	119.9
C1—C6—H6	120	C18—C17—H17	119.9
C8—C7—C12	119.3 (2)	C17—C18—C13	120.8 (2)
C8—C7—P1	118.76 (18)	C17—C18—H18	119.6
C12—C7—P1	121.91 (18)	C13—C18—H18	119.6
C9—C8—C7	120.4 (2)	C14—C19—H19A	109.5
C9—C8—H8	119.8	C14—C19—H19B	109.5
C7—C8—H8	119.8	H19A—C19—H19B	109.5
C10—C9—C8	119.9 (2)	C14—C19—H19C	109.5
C10—C9—H9	120	H19A—C19—H19C	109.5
C8—C9—H9	120	H19B—C19—H19C	109.5
C7—P1—C1—C2	−161.45 (19)	C8—C9—C10—C11	0.9 (4)
C13—P1—C1—C2	85.7 (2)	C9—C10—C11—C12	−0.3 (4)
Se1—P1—C1—C2	−38.0 (2)	C10—C11—C12—C7	−0.5 (4)
C7—P1—C1—C6	18.3 (2)	C8—C7—C12—C11	0.6 (4)
C13—P1—C1—C6	−94.6 (2)	P1—C7—C12—C11	179.3 (2)
Se1—P1—C1—C6	141.75 (17)	C7—P1—C13—C18	−119.28 (19)
C6—C1—C2—C3	0.4 (4)	C1—P1—C13—C18	−7.6 (2)
P1—C1—C2—C3	−179.89 (18)	Se1—P1—C13—C18	114.96 (18)
C1—C2—C3—C4	−1.4 (4)	C7—P1—C13—C14	65.8 (2)
C2—C3—C4—C5	1.1 (4)	C1—P1—C13—C14	177.43 (19)
C3—C4—C5—C6	0.2 (4)	Se1—P1—C13—C14	−60.0 (2)
C4—C5—C6—C1	−1.3 (4)	C18—C13—C14—C15	−1.5 (3)
C2—C1—C6—C5	1.0 (3)	P1—C13—C14—C15	173.43 (18)
P1—C1—C6—C5	−178.77 (18)	C18—C13—C14—C19	177.5 (2)
C1—P1—C7—C8	91.0 (2)	P1—C13—C14—C19	−7.6 (3)
C13—P1—C7—C8	−156.19 (19)	C13—C14—C15—C16	1.8 (4)
Se1—P1—C7—C8	−30.9 (2)	C19—C14—C15—C16	−177.2 (2)
C1—P1—C7—C12	−87.7 (2)	C14—C15—C16—C17	−0.9 (4)
C13—P1—C7—C12	25.2 (2)	C15—C16—C17—C18	−0.2 (4)
Se1—P1—C7—C12	150.51 (18)	C16—C17—C18—C13	0.5 (4)
C12—C7—C8—C9	0.0 (4)	C14—C13—C18—C17	0.4 (3)
P1—C7—C8—C9	−178.71 (18)	P1—C13—C18—C17	−174.62 (18)
C7—C8—C9—C10	−0.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···Se1	0.98	2.90	3.670 (3)	136
C9—H9···Cg1^i	0.95	2.97	3.700 (3)	134
C2—H2···Cg2^ii	0.95	2.96	3.673 (3)	133

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z.

Dicyclohexyl(2-methylphenyl)phosphane selenide (mo_12fm_wld10b_0m)

Crystal data

C19H29PSe	F(000) = 1536
Mr = 367.35	Dx = 1.325 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4902 reflections
a = 12.267 (2) Å	θ = 2.4–26.6°
b = 10.2092 (15) Å	µ = 2.12 mm^−1
c = 29.422 (5) Å	T = 100 K
β = 92.097 (4)°	Needle, colourless
V = 3682.3 (10) Å^3	0.25 × 0.08 × 0.07 mm
Z = 8

Data collection

Bruker APEX DUO 4K CCD diffractometer	9098 independent reflections
Radiation source: sealed tube	6339 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
Detector resolution: 8.4 pixels mm^-1	θmax = 28.3°, θmin = 1.7°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −12→13
Tmin = 0.619, Tmax = 0.866	l = −38→39
38052 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0401P)^2 + 7.6673P] where P = (Fo^2 + 2Fc^2)/3
9098 reflections	(Δ/σ)max = 0.002
381 parameters	Δρmax = 1.93 e Å^−3
0 restraints	Δρmin = −0.86 e Å^−3

Special details

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 60 s/frame. A total of 506 frames were collected with a frame width of 0.5° covering up to θ = 28.26° with 99.7% completeness accomplished.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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-ray diffraction experiments for compounds I and II were performed at 100 K with a Bruker APEX DUO diffractometer with Mo-Kα radiation (λ = 0.71073). Data collections were performed with a CCD detector using Apex2 software (Bruker, 2011) from a single crystal mounted on a glass fibre. The intensities were integrated from several series of exposures measuring 0.5° in ω or φ (Bruker, 2008). Absorption corrections based on equivalent reflections were applied by using SADABS (Bruker, 2008). The structures were solved by using SIR97 (Altomare et al., 1999) and refined against all Fo² data.

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

	x	y	z	Uiso*/Ueq
Se1	0.10334 (3)	0.87095 (4)	0.869021 (15)	0.02718 (11)
Se2	0.60706 (3)	0.60704 (4)	0.894610 (16)	0.02735 (11)
P1	−0.06923 (7)	0.87032 (9)	0.87151 (3)	0.01769 (19)
P2	0.43508 (7)	0.60512 (9)	0.88512 (3)	0.01646 (19)
C1	−0.1257 (3)	1.0379 (4)	0.86765 (13)	0.0191 (8)
C2	−0.0514 (3)	1.1391 (4)	0.86297 (18)	0.0401 (12)
H2	0.0241	1.1188	0.8619	0.048*
C3	−0.0838 (3)	1.2687 (4)	0.8598 (2)	0.0463 (14)
H3	−0.0315	1.3357	0.8554	0.056*
C4	−0.1929 (3)	1.3000 (4)	0.86295 (15)	0.0320 (10)
H4	−0.2161	1.3888	0.8622	0.038*
C5	−0.2673 (3)	1.2002 (4)	0.86717 (13)	0.0232 (8)
H5	−0.3425	1.2219	0.8682	0.028*
C6	−0.2373 (3)	1.0694 (4)	0.86998 (13)	0.0196 (8)
C7	−0.3271 (3)	0.9694 (4)	0.87573 (16)	0.0310 (10)
H7A	−0.333	0.9486	0.9081	0.047*
H7B	−0.3099	0.8895	0.859	0.047*
H7C	−0.3966	1.0054	0.8639	0.047*
C8	−0.1170 (3)	0.8029 (3)	0.92489 (12)	0.0187 (7)
H8	−0.1985	0.8031	0.9228	0.022*
C9	−0.0821 (3)	0.8894 (4)	0.96557 (13)	0.0246 (8)
H9A	−0.0014	0.8932	0.9681	0.03*
H9B	−0.1096	0.9795	0.9604	0.03*
C10	−0.1259 (4)	0.8364 (4)	1.00998 (14)	0.0303 (9)
H10A	−0.1001	0.8923	1.0357	0.036*
H10B	−0.2066	0.839	1.0085	0.036*
C11	−0.0875 (3)	0.6961 (4)	1.01803 (14)	0.0301 (9)
H11A	−0.1189	0.6619	1.0462	0.036*
H11B	−0.0071	0.6946	1.0221	0.036*
C12	−0.1223 (3)	0.6087 (4)	0.97800 (14)	0.0268 (9)
H12A	−0.0939	0.519	0.9834	0.032*
H12B	−0.2029	0.6038	0.9758	0.032*
C13	−0.0805 (3)	0.6600 (4)	0.93336 (13)	0.0236 (8)
H13A	−0.1085	0.604	0.908	0.028*
H13B	0.0002	0.6554	0.9341	0.028*
C14	−0.1358 (3)	0.7742 (4)	0.82499 (13)	0.0218 (8)
H14	−0.2062	0.7405	0.8366	0.026*
C15	−0.0679 (3)	0.6540 (4)	0.81165 (15)	0.0294 (9)
H15A	0.0027	0.6835	0.7999	0.035*
H15B	−0.0525	0.5991	0.8388	0.035*
C16	−0.1292 (4)	0.5731 (4)	0.77527 (15)	0.0350 (10)
H16A	−0.0835	0.4979	0.7665	0.042*
H16B	−0.1971	0.5382	0.7878	0.042*
C17	−0.1573 (4)	0.6554 (4)	0.73347 (15)	0.0381 (11)
H17A	−0.1992	0.6017	0.7109	0.046*
H17B	−0.0894	0.6846	0.7194	0.046*
C18	−0.2251 (4)	0.7751 (5)	0.74639 (15)	0.0391 (11)
H18A	−0.2958	0.7458	0.758	0.047*
H18B	−0.2401	0.8297	0.7191	0.047*
C19	−0.1639 (4)	0.8568 (4)	0.78295 (14)	0.0319 (9)
H19A	−0.096	0.8919	0.7705	0.038*
H19B	−0.2098	0.9319	0.7916	0.038*
C20	0.3799 (3)	0.4380 (3)	0.88597 (13)	0.0184 (7)
C21	0.2695 (3)	0.4049 (3)	0.87767 (12)	0.0192 (7)
C22	0.1789 (3)	0.5025 (4)	0.86829 (16)	0.0324 (10)
H22A	0.1679	0.5139	0.8354	0.049*
H22B	0.1987	0.5867	0.8823	0.049*
H22C	0.1115	0.4701	0.8811	0.049*
C23	0.2399 (3)	0.2727 (4)	0.87785 (13)	0.0234 (8)
H23	0.1659	0.2499	0.8713	0.028*
C24	0.3141 (3)	0.1741 (4)	0.88721 (14)	0.0255 (9)
H24	0.2918	0.085	0.8869	0.031*
C25	0.4215 (3)	0.2071 (4)	0.89709 (16)	0.0302 (10)
H25	0.4735	0.1407	0.9043	0.036*
C26	0.4534 (3)	0.3374 (4)	0.89645 (15)	0.0266 (9)
H26	0.5276	0.3587	0.9034	0.032*
C27	0.3885 (3)	0.6718 (3)	0.82909 (13)	0.0200 (8)
H27	0.3074	0.6619	0.827	0.024*
C28	0.4338 (4)	0.5906 (4)	0.79085 (15)	0.0349 (10)
H28A	0.4106	0.4983	0.7941	0.042*
H28B	0.5145	0.5933	0.7928	0.042*
C29	0.3931 (4)	0.6432 (5)	0.74428 (15)	0.0401 (11)
H29A	0.4272	0.5926	0.7199	0.048*
H29B	0.3131	0.6312	0.741	0.048*
C30	0.4206 (4)	0.7875 (4)	0.73915 (15)	0.0373 (11)
H30A	0.5007	0.799	0.74	0.045*
H30B	0.3913	0.8198	0.7094	0.045*
C31	0.3719 (4)	0.8660 (4)	0.77715 (15)	0.0348 (10)
H31A	0.2914	0.8591	0.7749	0.042*
H31B	0.3916	0.9595	0.7738	0.042*
C32	0.4129 (4)	0.8172 (4)	0.82340 (14)	0.0313 (10)
H32A	0.3774	0.8675	0.8475	0.038*
H32B	0.4926	0.8318	0.8267	0.038*
C33	0.3656 (3)	0.7009 (3)	0.92840 (12)	0.0166 (7)
H33	0.2942	0.7298	0.9143	0.02*
C34	0.4280 (3)	0.8256 (4)	0.94286 (14)	0.0237 (8)
H34A	0.4978	0.8014	0.9587	0.028*
H34B	0.4449	0.8776	0.9156	0.028*
C35	0.3594 (3)	0.9079 (4)	0.97454 (14)	0.0279 (9)
H35A	0.4008	0.987	0.9841	0.034*
H35B	0.2918	0.9365	0.958	0.034*
C36	0.3301 (4)	0.8303 (4)	1.01614 (14)	0.0330 (10)
H36A	0.2817	0.8837	1.0349	0.04*
H36B	0.3974	0.8111	1.0346	0.04*
C37	0.2729 (4)	0.7017 (4)	1.00355 (15)	0.0343 (10)
H37A	0.2004	0.7209	0.9892	0.041*
H37B	0.2617	0.6503	1.0315	0.041*
C38	0.3396 (3)	0.6206 (4)	0.97072 (14)	0.0283 (9)
H38A	0.298	0.5413	0.9615	0.034*
H38B	0.4085	0.5921	0.9863	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.01311 (16)	0.0241 (2)	0.0445 (3)	0.00118 (14)	0.00294 (15)	0.00667 (18)
Se2	0.01204 (16)	0.0204 (2)	0.0496 (3)	−0.00174 (14)	0.00098 (15)	−0.00165 (18)
P1	0.0138 (4)	0.0153 (5)	0.0240 (5)	−0.0002 (3)	−0.0003 (3)	0.0032 (4)
P2	0.0133 (4)	0.0133 (4)	0.0228 (5)	0.0002 (3)	0.0007 (3)	−0.0003 (4)
C1	0.0157 (16)	0.0216 (19)	0.020 (2)	0.0013 (13)	−0.0008 (14)	0.0023 (15)
C2	0.0189 (19)	0.025 (2)	0.077 (4)	−0.0003 (16)	0.000 (2)	0.010 (2)
C3	0.022 (2)	0.023 (2)	0.094 (4)	−0.0073 (17)	−0.001 (2)	0.013 (2)
C4	0.030 (2)	0.021 (2)	0.045 (3)	0.0031 (16)	0.0007 (19)	0.0058 (18)
C5	0.0202 (17)	0.027 (2)	0.022 (2)	0.0032 (15)	0.0019 (15)	−0.0013 (16)
C6	0.0161 (16)	0.0210 (19)	0.022 (2)	−0.0036 (14)	0.0017 (14)	0.0019 (15)
C7	0.0163 (17)	0.025 (2)	0.052 (3)	0.0002 (15)	0.0025 (18)	−0.0019 (19)
C8	0.0151 (15)	0.0198 (19)	0.021 (2)	0.0000 (13)	−0.0028 (14)	0.0029 (15)
C9	0.0301 (19)	0.0201 (19)	0.024 (2)	0.0014 (15)	0.0028 (16)	0.0000 (16)
C10	0.038 (2)	0.025 (2)	0.028 (2)	0.0020 (17)	0.0053 (18)	0.0022 (17)
C11	0.033 (2)	0.029 (2)	0.029 (2)	0.0009 (17)	0.0050 (18)	0.0057 (18)
C12	0.0293 (19)	0.020 (2)	0.031 (2)	−0.0019 (16)	−0.0001 (16)	0.0096 (17)
C13	0.0281 (19)	0.0172 (18)	0.025 (2)	−0.0019 (15)	−0.0005 (16)	0.0025 (16)
C14	0.0201 (17)	0.023 (2)	0.023 (2)	0.0011 (14)	0.0010 (15)	−0.0002 (16)
C15	0.031 (2)	0.026 (2)	0.032 (2)	0.0065 (16)	−0.0001 (17)	−0.0004 (18)
C16	0.046 (3)	0.026 (2)	0.033 (3)	0.0016 (19)	0.000 (2)	−0.0047 (19)
C17	0.053 (3)	0.034 (2)	0.027 (2)	0.000 (2)	0.001 (2)	−0.0057 (19)
C18	0.053 (3)	0.040 (3)	0.024 (2)	0.009 (2)	−0.003 (2)	−0.002 (2)
C19	0.044 (2)	0.031 (2)	0.021 (2)	0.0072 (18)	0.0016 (18)	−0.0001 (18)
C20	0.0166 (16)	0.0116 (17)	0.027 (2)	0.0020 (13)	−0.0018 (14)	−0.0001 (14)
C21	0.0174 (16)	0.0196 (19)	0.0204 (19)	0.0009 (14)	−0.0010 (14)	−0.0002 (15)
C22	0.0165 (17)	0.025 (2)	0.055 (3)	−0.0016 (15)	−0.0082 (18)	0.0053 (19)
C23	0.0183 (17)	0.023 (2)	0.029 (2)	−0.0063 (14)	−0.0043 (15)	0.0002 (16)
C24	0.0264 (19)	0.0160 (19)	0.034 (2)	−0.0050 (15)	−0.0028 (17)	−0.0005 (16)
C25	0.0232 (19)	0.018 (2)	0.050 (3)	0.0038 (15)	0.0011 (18)	0.0035 (18)
C26	0.0172 (17)	0.0193 (19)	0.043 (3)	−0.0013 (14)	−0.0030 (16)	0.0006 (17)
C27	0.0208 (17)	0.0187 (18)	0.020 (2)	−0.0028 (14)	−0.0023 (14)	−0.0009 (15)
C28	0.045 (3)	0.027 (2)	0.032 (3)	−0.0002 (19)	0.003 (2)	−0.0038 (19)
C29	0.055 (3)	0.041 (3)	0.024 (2)	−0.002 (2)	−0.001 (2)	−0.005 (2)
C30	0.043 (3)	0.042 (3)	0.026 (2)	−0.007 (2)	−0.002 (2)	0.007 (2)
C31	0.045 (2)	0.022 (2)	0.037 (3)	−0.0032 (18)	−0.007 (2)	0.0065 (19)
C32	0.045 (2)	0.024 (2)	0.024 (2)	−0.0031 (18)	−0.0063 (19)	0.0020 (17)
C33	0.0146 (15)	0.0162 (17)	0.0188 (19)	−0.0010 (13)	−0.0008 (13)	0.0002 (14)
C34	0.0254 (18)	0.0197 (19)	0.026 (2)	−0.0051 (15)	0.0009 (16)	−0.0060 (16)
C35	0.035 (2)	0.022 (2)	0.026 (2)	0.0008 (16)	0.0001 (17)	−0.0060 (17)
C36	0.043 (2)	0.032 (2)	0.024 (2)	−0.0001 (19)	0.0035 (18)	−0.0046 (18)
C37	0.046 (3)	0.034 (2)	0.024 (2)	−0.0091 (19)	0.0144 (19)	−0.0035 (18)
C38	0.036 (2)	0.021 (2)	0.028 (2)	−0.0052 (17)	0.0036 (17)	−0.0009 (17)

Geometric parameters (Å, º)

Se1—P1	2.1210 (10)	C18—H18A	0.99
Se2—P2	2.1181 (10)	C18—H18B	0.99
P1—C8	1.831 (4)	C19—H19A	0.99
P1—C1	1.848 (4)	C19—H19B	0.99
P1—C14	1.850 (4)	C20—C26	1.394 (5)
P2—C20	1.836 (4)	C20—C21	1.409 (5)
P2—C33	1.840 (4)	C21—C23	1.398 (5)
P2—C27	1.854 (4)	C21—C22	1.510 (5)
C1—C2	1.388 (5)	C22—H22A	0.98
C1—C6	1.411 (5)	C22—H22B	0.98
C2—C3	1.384 (6)	C22—H22C	0.98
C2—H2	0.95	C23—C24	1.379 (5)
C3—C4	1.382 (6)	C23—H23	0.95
C3—H3	0.95	C24—C25	1.381 (5)
C4—C5	1.376 (5)	C24—H24	0.95
C4—H4	0.95	C25—C26	1.386 (5)
C5—C6	1.387 (5)	C25—H25	0.95
C5—H5	0.95	C26—H26	0.95
C6—C7	1.516 (5)	C27—C28	1.519 (6)
C7—H7A	0.98	C27—C32	1.525 (5)
C7—H7B	0.98	C27—H27	1
C7—H7C	0.98	C28—C29	1.538 (6)
C8—C9	1.536 (5)	C28—H28A	0.99
C8—C13	1.544 (5)	C28—H28B	0.99
C8—H8	1	C29—C30	1.521 (6)
C9—C10	1.530 (5)	C29—H29A	0.99
C9—H9A	0.99	C29—H29B	0.99
C9—H9B	0.99	C30—C31	1.515 (6)
C10—C11	1.524 (6)	C30—H30A	0.99
C10—H10A	0.99	C30—H30B	0.99
C10—H10B	0.99	C31—C32	1.517 (6)
C11—C12	1.526 (6)	C31—H31A	0.99
C11—H11A	0.99	C31—H31B	0.99
C11—H11B	0.99	C32—H32A	0.99
C12—C13	1.520 (5)	C32—H32B	0.99
C12—H12A	0.99	C33—C38	1.534 (5)
C12—H12B	0.99	C33—C34	1.538 (5)
C13—H13A	0.99	C33—H33	1
C13—H13B	0.99	C34—C35	1.529 (5)
C14—C19	1.526 (5)	C34—H34A	0.99
C14—C15	1.542 (5)	C34—H34B	0.99
C14—H14	1	C35—C36	1.512 (6)
C15—C16	1.528 (6)	C35—H35A	0.99
C15—H15A	0.99	C35—H35B	0.99
C15—H15B	0.99	C36—C37	1.527 (6)
C16—C17	1.518 (6)	C36—H36A	0.99
C16—H16A	0.99	C36—H36B	0.99
C16—H16B	0.99	C37—C38	1.532 (6)
C17—C18	1.534 (6)	C37—H37A	0.99
C17—H17A	0.99	C37—H37B	0.99
C17—H17B	0.99	C38—H38A	0.99
C18—C19	1.535 (6)	C38—H38B	0.99
C8—P1—C1	105.68 (17)	C14—C19—C18	110.9 (4)
C8—P1—C14	106.77 (17)	C14—C19—H19A	109.5
C1—P1—C14	106.94 (16)	C18—C19—H19A	109.5
C8—P1—Se1	112.45 (11)	C14—C19—H19B	109.5
C1—P1—Se1	111.55 (12)	C18—C19—H19B	109.5
C14—P1—Se1	112.99 (12)	H19A—C19—H19B	108
C20—P2—C33	107.70 (16)	C26—C20—C21	118.2 (3)
C20—P2—C27	104.57 (16)	C26—C20—P2	116.9 (3)
C33—P2—C27	106.53 (16)	C21—C20—P2	125.0 (3)
C20—P2—Se2	111.88 (11)	C23—C21—C20	118.6 (3)
C33—P2—Se2	112.87 (11)	C23—C21—C22	116.6 (3)
C27—P2—Se2	112.76 (12)	C20—C21—C22	124.8 (3)
C2—C1—C6	118.5 (3)	C21—C22—H22A	109.5
C2—C1—P1	116.7 (3)	C21—C22—H22B	109.5
C6—C1—P1	124.8 (3)	H22A—C22—H22B	109.5
C3—C2—C1	122.0 (4)	C21—C22—H22C	109.5
C3—C2—H2	119	H22A—C22—H22C	109.5
C1—C2—H2	119	H22B—C22—H22C	109.5
C4—C3—C2	119.5 (4)	C24—C23—C21	122.4 (3)
C4—C3—H3	120.2	C24—C23—H23	118.8
C2—C3—H3	120.2	C21—C23—H23	118.8
C5—C4—C3	118.8 (4)	C23—C24—C25	118.8 (3)
C5—C4—H4	120.6	C23—C24—H24	120.6
C3—C4—H4	120.6	C25—C24—H24	120.6
C4—C5—C6	122.9 (3)	C24—C25—C26	119.9 (4)
C4—C5—H5	118.6	C24—C25—H25	120
C6—C5—H5	118.6	C26—C25—H25	120
C5—C6—C1	118.2 (3)	C25—C26—C20	121.9 (3)
C5—C6—C7	117.6 (3)	C25—C26—H26	119
C1—C6—C7	124.2 (3)	C20—C26—H26	119
C6—C7—H7A	109.5	C28—C27—C32	111.8 (3)
C6—C7—H7B	109.5	C28—C27—P2	110.4 (3)
H7A—C7—H7B	109.5	C32—C27—P2	113.6 (3)
C6—C7—H7C	109.5	C28—C27—H27	106.9
H7A—C7—H7C	109.5	C32—C27—H27	106.9
H7B—C7—H7C	109.5	P2—C27—H27	106.9
C9—C8—C13	110.3 (3)	C27—C28—C29	110.8 (4)
C9—C8—P1	111.3 (2)	C27—C28—H28A	109.5
C13—C8—P1	113.2 (3)	C29—C28—H28A	109.5
C9—C8—H8	107.3	C27—C28—H28B	109.5
C13—C8—H8	107.3	C29—C28—H28B	109.5
P1—C8—H8	107.3	H28A—C28—H28B	108.1
C10—C9—C8	111.4 (3)	C30—C29—C28	111.1 (4)
C10—C9—H9A	109.3	C30—C29—H29A	109.4
C8—C9—H9A	109.3	C28—C29—H29A	109.4
C10—C9—H9B	109.3	C30—C29—H29B	109.4
C8—C9—H9B	109.3	C28—C29—H29B	109.4
H9A—C9—H9B	108	H29A—C29—H29B	108
C11—C10—C9	110.4 (3)	C31—C30—C29	110.2 (4)
C11—C10—H10A	109.6	C31—C30—H30A	109.6
C9—C10—H10A	109.6	C29—C30—H30A	109.6
C11—C10—H10B	109.6	C31—C30—H30B	109.6
C9—C10—H10B	109.6	C29—C30—H30B	109.6
H10A—C10—H10B	108.1	H30A—C30—H30B	108.1
C10—C11—C12	110.7 (3)	C30—C31—C32	111.2 (4)
C10—C11—H11A	109.5	C30—C31—H31A	109.4
C12—C11—H11A	109.5	C32—C31—H31A	109.4
C10—C11—H11B	109.5	C30—C31—H31B	109.4
C12—C11—H11B	109.5	C32—C31—H31B	109.4
H11A—C11—H11B	108.1	H31A—C31—H31B	108
C13—C12—C11	111.8 (3)	C31—C32—C27	111.0 (3)
C13—C12—H12A	109.3	C31—C32—H32A	109.4
C11—C12—H12A	109.3	C27—C32—H32A	109.4
C13—C12—H12B	109.3	C31—C32—H32B	109.4
C11—C12—H12B	109.3	C27—C32—H32B	109.4
H12A—C12—H12B	107.9	H32A—C32—H32B	108
C12—C13—C8	111.1 (3)	C38—C33—C34	109.5 (3)
C12—C13—H13A	109.4	C38—C33—P2	113.1 (2)
C8—C13—H13A	109.4	C34—C33—P2	113.1 (2)
C12—C13—H13B	109.4	C38—C33—H33	106.9
C8—C13—H13B	109.4	C34—C33—H33	106.9
H13A—C13—H13B	108	P2—C33—H33	106.9
C19—C14—C15	110.0 (3)	C35—C34—C33	110.1 (3)
C19—C14—P1	112.8 (3)	C35—C34—H34A	109.6
C15—C14—P1	112.5 (3)	C33—C34—H34A	109.6
C19—C14—H14	107.1	C35—C34—H34B	109.6
C15—C14—H14	107.1	C33—C34—H34B	109.6
P1—C14—H14	107.1	H34A—C34—H34B	108.2
C16—C15—C14	110.6 (3)	C36—C35—C34	111.0 (3)
C16—C15—H15A	109.5	C36—C35—H35A	109.4
C14—C15—H15A	109.5	C34—C35—H35A	109.4
C16—C15—H15B	109.5	C36—C35—H35B	109.4
C14—C15—H15B	109.5	C34—C35—H35B	109.4
H15A—C15—H15B	108.1	H35A—C35—H35B	108
C17—C16—C15	111.1 (4)	C35—C36—C37	112.0 (3)
C17—C16—H16A	109.4	C35—C36—H36A	109.2
C15—C16—H16A	109.4	C37—C36—H36A	109.2
C17—C16—H16B	109.4	C35—C36—H36B	109.2
C15—C16—H16B	109.4	C37—C36—H36B	109.2
H16A—C16—H16B	108	H36A—C36—H36B	107.9
C16—C17—C18	110.4 (4)	C36—C37—C38	111.5 (4)
C16—C17—H17A	109.6	C36—C37—H37A	109.3
C18—C17—H17A	109.6	C38—C37—H37A	109.3
C16—C17—H17B	109.6	C36—C37—H37B	109.3
C18—C17—H17B	109.6	C38—C37—H37B	109.3
H17A—C17—H17B	108.1	H37A—C37—H37B	108
C17—C18—C19	110.6 (4)	C37—C38—C33	110.8 (3)
C17—C18—H18A	109.5	C37—C38—H38A	109.5
C19—C18—H18A	109.5	C33—C38—H38A	109.5
C17—C18—H18B	109.5	C37—C38—H38B	109.5
C19—C18—H18B	109.5	C33—C38—H38B	109.5
H18A—C18—H18B	108.1	H38A—C38—H38B	108.1
C8—P1—C1—C2	123.6 (3)	C33—P2—C20—C26	−119.1 (3)
C14—P1—C1—C2	−122.9 (4)	C27—P2—C20—C26	127.8 (3)
Se1—P1—C1—C2	1.1 (4)	Se2—P2—C20—C26	5.5 (4)
C8—P1—C1—C6	−55.2 (4)	C33—P2—C20—C21	59.7 (4)
C14—P1—C1—C6	58.3 (4)	C27—P2—C20—C21	−53.3 (4)
Se1—P1—C1—C6	−177.7 (3)	Se2—P2—C20—C21	−175.7 (3)
C6—C1—C2—C3	−1.1 (7)	C26—C20—C21—C23	−3.5 (6)
P1—C1—C2—C3	−179.9 (4)	P2—C20—C21—C23	177.7 (3)
C1—C2—C3—C4	2.4 (8)	C26—C20—C21—C22	176.7 (4)
C2—C3—C4—C5	−2.9 (8)	P2—C20—C21—C22	−2.1 (6)
C3—C4—C5—C6	2.3 (7)	C20—C21—C23—C24	2.0 (6)
C4—C5—C6—C1	−1.0 (6)	C22—C21—C23—C24	−178.1 (4)
C4—C5—C6—C7	178.5 (4)	C21—C23—C24—C25	0.5 (6)
C2—C1—C6—C5	0.4 (6)	C23—C24—C25—C26	−1.5 (7)
P1—C1—C6—C5	179.1 (3)	C24—C25—C26—C20	−0.1 (7)
C2—C1—C6—C7	−179.1 (4)	C21—C20—C26—C25	2.6 (6)
P1—C1—C6—C7	−0.4 (6)	P2—C20—C26—C25	−178.5 (3)
C1—P1—C8—C9	−56.9 (3)	C20—P2—C27—C28	−61.0 (3)
C14—P1—C8—C9	−170.5 (2)	C33—P2—C27—C28	−174.9 (3)
Se1—P1—C8—C9	65.0 (3)	Se2—P2—C27—C28	60.8 (3)
C1—P1—C8—C13	178.2 (2)	C20—P2—C27—C32	172.5 (3)
C14—P1—C8—C13	64.6 (3)	C33—P2—C27—C32	58.6 (3)
Se1—P1—C8—C13	−59.9 (3)	Se2—P2—C27—C32	−65.7 (3)
C13—C8—C9—C10	−55.9 (4)	C32—C27—C28—C29	−54.0 (5)
P1—C8—C9—C10	177.6 (3)	P2—C27—C28—C29	178.5 (3)
C8—C9—C10—C11	57.3 (4)	C27—C28—C29—C30	55.4 (5)
C9—C10—C11—C12	−56.9 (4)	C28—C29—C30—C31	−57.2 (5)
C10—C11—C12—C13	56.6 (4)	C29—C30—C31—C32	57.9 (5)
C11—C12—C13—C8	−55.5 (4)	C30—C31—C32—C27	−56.6 (5)
C9—C8—C13—C12	54.6 (4)	C28—C27—C32—C31	54.8 (5)
P1—C8—C13—C12	−179.9 (3)	P2—C27—C32—C31	−179.5 (3)
C8—P1—C14—C19	144.8 (3)	C20—P2—C33—C38	35.3 (3)
C1—P1—C14—C19	32.1 (3)	C27—P2—C33—C38	147.0 (3)
Se1—P1—C14—C19	−91.0 (3)	Se2—P2—C33—C38	−88.7 (3)
C8—P1—C14—C15	−90.1 (3)	C20—P2—C33—C34	160.6 (3)
C1—P1—C14—C15	157.1 (3)	C27—P2—C33—C34	−87.7 (3)
Se1—P1—C14—C15	34.0 (3)	Se2—P2—C33—C34	36.6 (3)
C19—C14—C15—C16	−57.0 (4)	C38—C33—C34—C35	−59.4 (4)
P1—C14—C15—C16	176.5 (3)	P2—C33—C34—C35	173.4 (3)
C14—C15—C16—C17	57.5 (5)	C33—C34—C35—C36	58.1 (4)
C15—C16—C17—C18	−57.3 (5)	C34—C35—C36—C37	−55.1 (5)
C16—C17—C18—C19	56.8 (5)	C35—C36—C37—C38	53.6 (5)
C15—C14—C19—C18	57.0 (4)	C36—C37—C38—C33	−55.0 (5)
P1—C14—C19—C18	−176.6 (3)	C34—C33—C38—C37	57.9 (4)
C17—C18—C19—C14	−57.2 (5)	P2—C33—C38—C37	−174.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Se1	0.95	2.72	3.332 (4)	123
C26—H26···Se2	0.95	2.73	3.338 (4)	122
C33—H33···Se1	1.00	3.02	4.001 (4)	168