Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046594/hb2546sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046594/hb2546Isup2.hkl |
CCDC reference: 663842
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.
The H atoms were positioned geometrically (C—H = 0.95–0.98 Å) and refined as riding with Uiso(H) = 1.2 Ueq(C).
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).
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).
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).
C26H24P2Se2 | Z = 2 |
Mr = 556.31 | F(000) = 556 |
Triclinic, P1 | Dx = 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 |
Nonius KappaCCD area-detector diffractometer | 4095 independent reflections |
Radiation source: fine-focus sealed tube | 3328 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.099 |
φ scans, and ω scans with κ offsets | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (XPREP in SHELXTL; Bruker, 2001) | h = −12→12 |
Tmin = 0.738, Tmax = 0.855 | k = −12→12 |
14810 measured reflections | l = −14→14 |
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(Fo2) + (0.0852P)2 + 2.3976P] where P = (Fo2 + 2Fc2)/3 |
4095 reflections | (Δ/σ)max = 0.001 |
271 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.75 e Å−3 |
C26H24P2Se2 | γ = 112.14 (3)° |
Mr = 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)° |
Nonius KappaCCD area-detector diffractometer | 4095 independent reflections |
Absorption correction: multi-scan (XPREP in SHELXTL; Bruker, 2001) | 3328 reflections with I > 2σ(I) |
Tmin = 0.738, Tmax = 0.855 | Rint = 0.099 |
14810 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.58 e Å−3 |
4095 reflections | Δρmin = −0.75 e Å−3 |
271 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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. |
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···Se2iv | 0.95 | 3.01 | 3.954 (6) | 171 |
C14—H14···Se2v | 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 |
Mr | 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) |
Tmin, Tmax | 0.738, 0.855 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14810, 4095, 3328 |
Rint | 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 |
Δρmax, Δρmin (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).
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···Se2iv | 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. |
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).