1,2-Bis(Diphenyl­phosphino­selenoyl)­ethane

Risto, M.; Jahr, E.M.; Oilunkaniemi, R.; Laitinen, R.S.

doi:10.1107/S1600536807046594

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1,2-Bis(Diphenylphosphinoselenoyl)ethane

M. Risto, E. M. Jahr, R. Oilunkaniemi and R. S. Laitinen

In the title compound, (CH₂)₂(PPh₂)₂Se₂ or C₂₆H₂₄P₂Se₂, there are two half-molecules in the asymmetric unit, both molecules having inversion symmetry. The P—Se bond lengths suggest weak double-bond character. Weak C—H

Se hydrogen bonds help to assemble the molecules into a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046594/hb2546sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046594/hb2546Isup2.hkl Contains datablock I

CCDC reference: 663842

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.009 Å
R factor = 0.052
wR factor = 0.160
Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  SE1     ..       3.03 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H25    ..  SE2     ..       3.01 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24    ..  SE2     ..       2.99 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The crystals of the title compound, (I), (CH₂)₂(PPh₂)₂Se₂, were isolated as a side product during the synthesis (Risto et al., 2007) of [Pd(SeC₄H₄S)₂(dppe)] (dppe = diphenylphosphine) from [PdCl₂(dppe)] and LiSeC₄H₄S (prepared from thiophene, n-butyllithium, and an excess of elemental selenium). The asymmetric unit of (I) consists of two independent half-molecules, both molecular environments being completed by crystallographic inversion symmetry (Fig. 1). The two independent P—Se bond lengths are 2.104 (2) and 2.109 (2) Å indicating a slight double bond character [the sum of the covalent radii of phosphorus and selenium is 2.22 Å (Emsley 1998)]. The other bonds show normal single bond lengths. The molecules are assembled into a three-dimensional network by weak C—H···Se interactions (Table 2, Fig. 2).

Related literature top

For further details, see: Risto et al. (2007). For a related structure and background, see: Brown et al. (1980). For reference structural data, see: Emsley (1998).

Experimental top

The crystals of the title compound were isolated in synthesis of [Pd(SeC₄H₄S)₂(dppe)] from [PdCl₂(dppe)] (0.387 g, 0.673 mmol, in 15 ml dichloromethane) and lithium 2-thienylselenolate (1.474 mmol in 4.1 ml tetrahydrofuran, prepared from thiophene, n-butyllithium, and an excess of elemental selenium; used in situ). Colourless plates of (I) were obtained from the reaction mixture.

Structure description top

For further details, see: Risto et al. (2007). For a related structure and background, see: Brown et al. (1980). For reference structural data, see: Emsley (1998).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability limit. The unlabelled atoms in the C1 and C2 molecule are generated by the symmetry operations (-x, -y, 2 - z) and (-x, 1 - y, 1 - z), respectively.
	Fig. 2. The packing of molecules in (I) with C—H···Se interactions indicated by dashed lines.

1,2-bis(Diphenylphosphinoselenoyl)ethane top

Crystal data top

C₂₆H₂₄P₂Se₂	Z = 2
M_r = 556.31	F(000) = 556
Triclinic, P1	D_x = 1.544 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.322 (2) Å	Cell parameters from 3328 reflections
b = 10.843 (2) Å	θ = 2.3–25.0°
c = 12.285 (3) Å	µ = 3.24 mm⁻¹
α = 90.93 (3)°	T = 120 K
β = 108.13 (3)°	Plate, colourless
γ = 112.14 (3)°	0.10 × 0.10 × 0.05 mm
V = 1196.3 (4) Å³

Data collection top

Nonius KappaCCD area-detector diffractometer	4095 independent reflections
Radiation source: fine-focus sealed tube	3328 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
φ scans, and ω scans with κ offsets	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (XPREP in SHELXTL; Bruker, 2001)	h = −12→12
T_min = 0.738, T_max = 0.855	k = −12→12
14810 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0852P)² + 2.3976P] where P = (F_o² + 2F_c²)/3
4095 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

C₂₆H₂₄P₂Se₂	γ = 112.14 (3)°
M_r = 556.31	V = 1196.3 (4) Å³
Triclinic, P1	Z = 2
a = 10.322 (2) Å	Mo Kα radiation
b = 10.843 (2) Å	µ = 3.24 mm⁻¹
c = 12.285 (3) Å	T = 120 K
α = 90.93 (3)°	0.10 × 0.10 × 0.05 mm
β = 108.13 (3)°

Data collection top

Nonius KappaCCD area-detector diffractometer	4095 independent reflections
Absorption correction: multi-scan (XPREP in SHELXTL; Bruker, 2001)	3328 reflections with I > 2σ(I)
T_min = 0.738, T_max = 0.855	R_int = 0.099
14810 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.11	Δρ_max = 0.58 e Å⁻³
4095 reflections	Δρ_min = −0.75 e Å⁻³
271 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Se1	0.37097 (7)	0.12472 (6)	1.09921 (5)	0.0283 (2)
Se2	0.76343 (7)	0.38570 (6)	0.51739 (5)	0.0245 (2)
P1	0.19425 (17)	0.09757 (15)	0.94441 (13)	0.0179 (3)
P2	0.60174 (16)	0.36746 (14)	0.59353 (13)	0.0172 (3)
C1	0.0226 (7)	0.0653 (6)	0.9721 (5)	0.0212 (13)
H1A	0.0360	0.1426	1.0248	0.025*
H1B	−0.0577	0.0553	0.8985	0.025*
C2	0.5289 (7)	0.4973 (6)	0.5655 (5)	0.0202 (12)
H2A	0.4468	0.4785	0.5967	0.024*
H2B	0.6085	0.5859	0.6060	0.024*
C11	0.1511 (6)	−0.0439 (6)	0.8372 (5)	0.0168 (12)
C12	0.0077 (7)	−0.1131 (6)	0.7594 (5)	0.0243 (13)
H12	−0.0697	−0.0870	0.7616	0.029*
C13	−0.0230 (7)	−0.2195 (6)	0.6788 (5)	0.0251 (14)
H13	−0.1215	−0.2672	0.6263	0.030*
C14	0.0889 (7)	−0.2562 (6)	0.6748 (5)	0.0264 (14)
H14	0.0674	−0.3303	0.6201	0.032*
C15	0.2308 (7)	−0.1869 (6)	0.7489 (5)	0.0264 (14)
H15	0.3079	−0.2120	0.7442	0.032*
C16	0.2642 (7)	−0.0800 (6)	0.8311 (6)	0.0259 (14)
H16	0.3633	−0.0323	0.8825	0.031*
C21	0.2249 (6)	0.2447 (5)	0.8708 (5)	0.0173 (12)
C22	0.3695 (7)	0.3401 (6)	0.8960 (5)	0.0219 (13)
H22	0.4509	0.3281	0.9502	0.026*
C23	0.3934 (7)	0.4541 (6)	0.8404 (5)	0.0255 (14)
H23	0.4918	0.5199	0.8569	0.031*
C24	0.2746 (8)	0.4717 (6)	0.7614 (5)	0.0277 (15)
H24	0.2920	0.5492	0.7239	0.033*
C25	0.1316 (8)	0.3772 (6)	0.7374 (6)	0.0301 (15)
H25	0.0501	0.3897	0.6840	0.036*
C26	0.1073 (7)	0.2630 (6)	0.7919 (5)	0.0264 (14)
H26	0.0089	0.1970	0.7747	0.032*
C31	0.4360 (7)	0.2109 (6)	0.5413 (5)	0.0190 (12)
C32	0.3272 (7)	0.1831 (6)	0.5921 (5)	0.0235 (13)
H32	0.3376	0.2484	0.6503	0.028*
C33	0.2047 (7)	0.0625 (6)	0.5595 (5)	0.0274 (14)
H33	0.1324	0.0433	0.5964	0.033*
C34	0.1881 (7)	−0.0310 (6)	0.4719 (6)	0.0286 (15)
H34	0.1037	−0.1145	0.4485	0.034*
C35	0.2937 (7)	−0.0027 (6)	0.4188 (6)	0.0303 (15)
H35	0.2811	−0.0668	0.3586	0.036*
C36	0.4176 (7)	0.1178 (6)	0.4524 (5)	0.0237 (13)
H36	0.4896	0.1370	0.4152	0.028*
C41	0.6711 (6)	0.3761 (6)	0.7497 (5)	0.0182 (12)
C42	0.7566 (7)	0.5016 (6)	0.8218 (5)	0.0255 (14)
H42	0.7743	0.5828	0.7894	0.031*
C43	0.8148 (8)	0.5053 (7)	0.9404 (6)	0.0314 (15)
H43	0.8712	0.5896	0.9896	0.038*
C44	0.7916 (8)	0.3880 (7)	0.9876 (6)	0.0299 (15)
H44	0.8316	0.3916	1.0691	0.036*
C45	0.7107 (8)	0.2655 (7)	0.9171 (5)	0.0308 (15)
H45	0.6963	0.1849	0.9501	0.037*
C46	0.6504 (7)	0.2584 (6)	0.7992 (5)	0.0256 (14)
H46	0.5946	0.1732	0.7513	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0319 (4)	0.0263 (4)	0.0202 (4)	0.0109 (3)	0.0013 (3)	0.0036 (3)
Se2	0.0223 (4)	0.0299 (4)	0.0237 (4)	0.0112 (3)	0.0101 (3)	0.0055 (3)
P1	0.0202 (8)	0.0160 (7)	0.0177 (8)	0.0061 (6)	0.0080 (6)	0.0042 (6)
P2	0.0197 (8)	0.0165 (8)	0.0156 (8)	0.0078 (6)	0.0057 (6)	0.0043 (6)
C1	0.029 (3)	0.019 (3)	0.028 (3)	0.014 (3)	0.021 (3)	0.012 (3)
C2	0.021 (3)	0.015 (3)	0.018 (3)	0.005 (2)	0.002 (2)	0.002 (2)
C11	0.017 (3)	0.021 (3)	0.015 (3)	0.007 (2)	0.008 (2)	0.007 (2)
C12	0.022 (3)	0.028 (3)	0.027 (3)	0.010 (3)	0.013 (3)	0.012 (3)
C13	0.024 (3)	0.022 (3)	0.020 (3)	0.001 (3)	0.005 (3)	−0.001 (3)
C14	0.034 (4)	0.021 (3)	0.021 (3)	0.006 (3)	0.013 (3)	−0.001 (3)
C15	0.030 (4)	0.028 (3)	0.027 (3)	0.015 (3)	0.014 (3)	0.003 (3)
C16	0.021 (3)	0.025 (3)	0.032 (4)	0.009 (3)	0.009 (3)	0.005 (3)
C21	0.021 (3)	0.013 (3)	0.018 (3)	0.004 (2)	0.010 (2)	−0.002 (2)
C22	0.025 (3)	0.022 (3)	0.021 (3)	0.010 (3)	0.010 (3)	0.001 (2)
C23	0.033 (4)	0.018 (3)	0.030 (4)	0.007 (3)	0.019 (3)	0.003 (3)
C24	0.046 (4)	0.016 (3)	0.024 (3)	0.012 (3)	0.016 (3)	0.006 (3)
C25	0.034 (4)	0.028 (4)	0.026 (4)	0.013 (3)	0.007 (3)	0.011 (3)
C26	0.022 (3)	0.019 (3)	0.028 (4)	0.000 (3)	0.007 (3)	0.002 (3)
C31	0.025 (3)	0.014 (3)	0.018 (3)	0.009 (3)	0.006 (2)	0.004 (2)
C32	0.023 (3)	0.022 (3)	0.022 (3)	0.007 (3)	0.007 (3)	0.001 (3)
C33	0.026 (3)	0.025 (3)	0.025 (3)	0.004 (3)	0.009 (3)	0.003 (3)
C34	0.025 (3)	0.024 (3)	0.026 (4)	0.005 (3)	0.001 (3)	0.009 (3)
C35	0.031 (4)	0.019 (3)	0.033 (4)	0.007 (3)	0.004 (3)	−0.010 (3)
C36	0.021 (3)	0.024 (3)	0.025 (3)	0.011 (3)	0.004 (3)	0.004 (3)
C41	0.018 (3)	0.019 (3)	0.020 (3)	0.008 (2)	0.009 (2)	0.007 (2)
C42	0.031 (4)	0.019 (3)	0.025 (3)	0.011 (3)	0.008 (3)	0.005 (3)
C43	0.037 (4)	0.030 (4)	0.025 (4)	0.014 (3)	0.007 (3)	0.006 (3)
C44	0.036 (4)	0.038 (4)	0.017 (3)	0.017 (3)	0.007 (3)	0.009 (3)
C45	0.038 (4)	0.035 (4)	0.022 (4)	0.020 (3)	0.008 (3)	0.012 (3)
C46	0.032 (4)	0.021 (3)	0.020 (3)	0.011 (3)	0.004 (3)	0.005 (3)

Geometric parameters (Å, º) top

P1—Se1	2.1093 (19)	C23—C24	1.387 (9)
P2—Se2	2.1042 (16)	C23—H23	0.9500
P1—C1	1.814 (6)	C24—C25	1.377 (9)
P1—C21	1.819 (6)	C24—H24	0.9500
P1—C11	1.828 (6)	C25—C26	1.394 (9)
P2—C41	1.814 (6)	C25—H25	0.9500
P2—C31	1.820 (6)	C26—H26	0.9500
P2—C2	1.822 (6)	C31—C32	1.389 (8)
C1—C1ⁱ	1.557 (11)	C31—C36	1.392 (8)
C1—H1A	0.9900	C32—C33	1.375 (9)
C1—H1B	0.9900	C32—H32	0.9500
C2—C2ⁱⁱ	1.544 (11)	C33—C34	1.390 (9)
C2—H2A	0.9900	C33—H33	0.9500
C2—H2B	0.9900	C34—C35	1.380 (10)
C11—C16	1.385 (8)	C34—H34	0.9500
C11—C12	1.388 (8)	C35—C36	1.382 (9)
C12—C13	1.379 (9)	C35—H35	0.9500
C12—H12	0.9500	C36—H36	0.9500
C13—C14	1.369 (9)	C41—C46	1.394 (8)
C13—H13	0.9500	C41—C42	1.409 (8)
C14—C15	1.363 (9)	C42—C43	1.387 (9)
C14—H14	0.9500	C42—H42	0.9500
C15—C16	1.387 (9)	C43—C44	1.376 (9)
C15—H15	0.9500	C43—H43	0.9500
C16—H16	0.9500	C44—C45	1.374 (10)
C21—C26	1.380 (9)	C44—H44	0.9500
C21—C22	1.390 (8)	C45—C46	1.375 (9)
C22—C23	1.399 (9)	C45—H45	0.9500
C22—H22	0.9500	C46—H46	0.9500

C1—P1—C21	105.2 (3)	C24—C23—C22	120.5 (6)
C1—P1—C11	105.5 (3)	C24—C23—H23	119.7
C21—P1—C11	106.3 (2)	C22—C23—H23	119.7
C1—P1—Se1	111.2 (2)	C25—C24—C23	120.2 (6)
C21—P1—Se1	113.4 (2)	C25—C24—H24	119.9
C11—P1—Se1	114.52 (19)	C23—C24—H24	119.9
C41—P2—C31	105.4 (3)	C24—C25—C26	119.5 (6)
C41—P2—C2	106.5 (3)	C24—C25—H25	120.3
C31—P2—C2	103.7 (3)	C26—C25—H25	120.3
C41—P2—Se2	112.92 (19)	C21—C26—C25	120.7 (6)
C31—P2—Se2	114.43 (19)	C21—C26—H26	119.7
C2—P2—Se2	113.1 (2)	C25—C26—H26	119.7
C1ⁱ—C1—P1	110.4 (5)	C32—C31—C36	119.6 (6)
C1ⁱ—C1—H1A	109.6	C32—C31—P2	119.4 (4)
P1—C1—H1A	109.6	C36—C31—P2	121.0 (5)
C1ⁱ—C1—H1B	109.6	C33—C32—C31	121.0 (6)
P1—C1—H1B	109.6	C33—C32—H32	119.5
H1A—C1—H1B	108.1	C31—C32—H32	119.5
C2ⁱⁱ—C2—P2	111.1 (5)	C32—C33—C34	119.2 (6)
C2ⁱⁱ—C2—H2A	109.4	C32—C33—H33	120.4
P2—C2—H2A	109.4	C34—C33—H33	120.4
C2ⁱⁱ—C2—H2B	109.4	C35—C34—C33	120.2 (6)
P2—C2—H2B	109.4	C35—C34—H34	119.9
H2A—C2—H2B	108.0	C33—C34—H34	119.9
C16—C11—C12	119.4 (5)	C34—C35—C36	120.7 (6)
C16—C11—P1	119.5 (4)	C34—C35—H35	119.7
C12—C11—P1	121.1 (4)	C36—C35—H35	119.7
C13—C12—C11	120.4 (6)	C35—C36—C31	119.4 (6)
C13—C12—H12	119.8	C35—C36—H36	120.3
C11—C12—H12	119.8	C31—C36—H36	120.3
C14—C13—C12	119.8 (6)	C46—C41—C42	119.1 (5)
C14—C13—H13	120.1	C46—C41—P2	120.3 (4)
C12—C13—H13	120.1	C42—C41—P2	120.4 (4)
C15—C14—C13	120.3 (6)	C43—C42—C41	119.3 (6)
C15—C14—H14	119.8	C43—C42—H42	120.4
C13—C14—H14	119.8	C41—C42—H42	120.4
C14—C15—C16	120.9 (6)	C44—C43—C42	120.6 (6)
C14—C15—H15	119.6	C44—C43—H43	119.7
C16—C15—H15	119.6	C42—C43—H43	119.7
C11—C16—C15	119.2 (6)	C45—C44—C43	120.1 (6)
C11—C16—H16	120.4	C45—C44—H44	120.0
C15—C16—H16	120.4	C43—C44—H44	120.0
C26—C21—C22	120.1 (5)	C44—C45—C46	120.7 (6)
C26—C21—P1	121.1 (4)	C44—C45—H45	119.7
C22—C21—P1	118.8 (5)	C46—C45—H45	119.7
C21—C22—C23	119.0 (6)	C45—C46—C41	120.2 (6)
C21—C22—H22	120.5	C45—C46—H46	119.9
C23—C22—H22	120.5	C41—C46—H46	119.9

C21—P1—C1—C1ⁱ	176.1 (6)	C22—C21—C26—C25	−0.5 (9)
C11—P1—C1—C1ⁱ	64.0 (6)	P1—C21—C26—C25	178.9 (5)
Se1—P1—C1—C1ⁱ	−60.7 (6)	C24—C25—C26—C21	0.9 (10)
C41—P2—C2—C2ⁱⁱ	178.1 (5)	C41—P2—C31—C32	50.1 (5)
C31—P2—C2—C2ⁱⁱ	−70.9 (6)	C2—P2—C31—C32	−61.6 (5)
Se2—P2—C2—C2ⁱⁱ	53.6 (6)	Se2—P2—C31—C32	174.8 (4)
C1—P1—C11—C16	−154.2 (5)	C41—P2—C31—C36	−128.9 (5)
C21—P1—C11—C16	94.5 (5)	C2—P2—C31—C36	119.4 (5)
Se1—P1—C11—C16	−31.5 (5)	Se2—P2—C31—C36	−4.2 (5)
C1—P1—C11—C12	27.9 (5)	C36—C31—C32—C33	2.8 (9)
C21—P1—C11—C12	−83.5 (5)	P2—C31—C32—C33	−176.2 (5)
Se1—P1—C11—C12	150.5 (4)	C31—C32—C33—C34	−1.9 (10)
C16—C11—C12—C13	1.9 (9)	C32—C33—C34—C35	0.2 (10)
P1—C11—C12—C13	179.9 (5)	C33—C34—C35—C36	0.5 (10)
C11—C12—C13—C14	−0.7 (9)	C34—C35—C36—C31	0.5 (10)
C12—C13—C14—C15	−0.9 (9)	C32—C31—C36—C35	−2.1 (9)
C13—C14—C15—C16	1.3 (10)	P2—C31—C36—C35	176.9 (5)
C12—C11—C16—C15	−1.5 (9)	C31—P2—C41—C46	31.2 (5)
P1—C11—C16—C15	−179.5 (5)	C2—P2—C41—C46	140.9 (5)
C14—C15—C16—C11	−0.1 (9)	Se2—P2—C41—C46	−94.4 (5)
C1—P1—C21—C26	−37.1 (5)	C31—P2—C41—C42	−153.9 (5)
C11—P1—C21—C26	74.4 (5)	C2—P2—C41—C42	−44.2 (5)
Se1—P1—C21—C26	−158.9 (4)	Se2—P2—C41—C42	80.4 (5)
C1—P1—C21—C22	142.3 (5)	C46—C41—C42—C43	−1.8 (9)
C11—P1—C21—C22	−106.2 (5)	P2—C41—C42—C43	−176.7 (5)
Se1—P1—C21—C22	20.5 (5)	C41—C42—C43—C44	1.0 (10)
C26—C21—C22—C23	0.0 (8)	C42—C43—C44—C45	0.3 (10)
P1—C21—C22—C23	−179.4 (4)	C43—C44—C45—C46	−0.9 (10)
C21—C22—C23—C24	0.1 (9)	C44—C45—C46—C41	0.1 (10)
C22—C23—C24—C25	0.3 (9)	C42—C41—C46—C45	1.2 (9)
C23—C24—C25—C26	−0.7 (9)	P2—C41—C46—C45	176.2 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Se1ⁱⁱⁱ	0.95	3.03	3.732 (6)	132
C25—H25···Se2^iv	0.95	3.01	3.954 (6)	171
C14—H14···Se2^v	0.95	2.98	3.690 (7)	133
C24—H24···Se2ⁱⁱ	0.95	2.99	3.751 (6)	138

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄P₂Se₂
M_r	556.31
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	10.322 (2), 10.843 (2), 12.285 (3)
α, β, γ (°)	90.93 (3), 108.13 (3), 112.14 (3)
V (Å³)	1196.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.24
Crystal size (mm)	0.10 × 0.10 × 0.05

Data collection
Diffractometer	Nonius KappaCCD area-detector
Absorption correction	Multi-scan (XPREP in SHELXTL; Bruker, 2001)
T_min, T_max	0.738, 0.855
No. of measured, independent and observed [I > 2σ(I)] reflections	14810, 4095, 3328
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.160, 1.11
No. of reflections	4095
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.75

Computer programs: COLLECT (Nonius, 1998), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg & Berndt, 1999), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

P1—Se1

2.1093 (19)

P2—Se2

2.1042 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Se1ⁱ	0.95	3.03	3.732 (6)	132
C25—H25···Se2ⁱⁱ	0.95	3.01	3.954 (6)	171
C14—H14···Se2ⁱⁱⁱ	0.95	2.98	3.690 (7)	133
C24—H24···Se2^iv	0.95	2.99	3.751 (6)	138

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

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