Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800018754/ob6003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800018754/ob6003Isup2.hkl |
CCDC reference: 155876
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.026
- wR factor = 0.075
- Data-to-parameter ratio = 21.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.27 From the CIF: _reflns_number_total 3080 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3283 Completeness (_total/calc) 93.82% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
To solution (0.500 g, 1.17 mmol) of 1,4-butylenebis(diphenylphosphine) or dppb in 20 ml dry benzene was added powdered selenium metal (0.185 g, 2.34 mmol) and the contents refluxed for 4 h. The solid Se was consumed during the reflux. The solution was filtered and the volume reduced by half. The product formed on the addition of 1 ml of dry ethanol; yield 0.685 g, 95%, m.p. 461–463 K. Single crystals were obtained from a solution of 100 mg of dppbSe2 in a 1:1 benzene–ethanol mixture. The preparation is based on that of Ph3PSe (Nicpon & Meek 1966), and analytical data and IR spectroscopy have been previously reported (Sandhu & Singh, 1976).
Crystal decay was assessed with a recollection the first 182 reflections at the end of the experiment.
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN for Windows (Molecular Structure Corporation, 1997).
Fig. 1. ORTEPII (Johnson, 1976; Hall et al., 1999) projection of (I) with displacement ellipsoids shown at the 20% probability level. |
C28H28P2Se2 | F(000) = 588 |
Mr = 584.36 | Dx = 1.465 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8206 (7) Å | Cell parameters from 918 reflections |
b = 23.154 (3) Å | θ = 2.6–27.7° |
c = 8.7018 (9) Å | µ = 2.93 mm−1 |
β = 105.380 (2)° | T = 294 K |
V = 1325.0 (2) Å3 | Prism, colourless |
Z = 2 | 0.60 × 0.25 × 0.19 mm |
Bruker SMART 1000 CCD diffractometer | 3080 independent reflections |
Radiation source: sealed tube | 2741 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 28.3°, θmin = 1.8° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996; Blessing, 1995) | h = −9→8 |
Tmin = 0.382, Tmax = 0.570 | k = −30→30 |
11599 measured reflections | l = −11→11 |
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)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0425P)2 + 0.4738P] where P = (Fo2 + 2Fc2)/3 |
3080 reflections | (Δ/σ)max = 0.002 |
145 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
C28H28P2Se2 | V = 1325.0 (2) Å3 |
Mr = 584.36 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.8206 (7) Å | µ = 2.93 mm−1 |
b = 23.154 (3) Å | T = 294 K |
c = 8.7018 (9) Å | 0.60 × 0.25 × 0.19 mm |
β = 105.380 (2)° |
Bruker SMART 1000 CCD diffractometer | 3080 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996; Blessing, 1995) | 2741 reflections with I > 2σ(I) |
Tmin = 0.382, Tmax = 0.570 | Rint = 0.017 |
11599 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.47 e Å−3 |
3080 reflections | Δρmin = −0.41 e Å−3 |
145 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. An empirical absorption correction determined with SADABS (Sheldrick, 1996 and Blessing 1995) was applied to the data. The data integration and reduction were undertaken with SAINT and XPREP (Bruker 1995) and subsequent computations were carried out with the TEXSAN (MSC 1995) graphical user interface. The data reduction included the application of Lorentz and polarization corrections, The structure was solved in the space group P21/n(#14) by direct methods with SIR97 (Altomare et al. 1993), and extended and refined with SHELXL97 (Sheldrick 1997). Anisotropic thermal parameters were refined for the non-hydrogen atoms, and a riding atom model was used for the hydrogen atoms included in the model. 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 | 0.07579 (3) | 0.066872 (10) | 0.75371 (3) | 0.05699 (10) | |
P1 | 0.38395 (6) | 0.088362 (18) | 0.78555 (5) | 0.03200 (10) | |
C1 | 0.4317 (3) | 0.02035 (7) | 0.53219 (19) | 0.0367 (3) | |
H1A | 0.4119 | 0.0559 | 0.4711 | 0.044* | |
H1B | 0.2997 | 0.0025 | 0.5194 | 0.044* | |
C2 | 0.5248 (2) | 0.03422 (7) | 0.70804 (19) | 0.0344 (3) | |
H2A | 0.6630 | 0.0478 | 0.7218 | 0.041* | |
H2B | 0.5311 | −0.0009 | 0.7698 | 0.041* | |
C3 | 0.4174 (3) | 0.15610 (7) | 0.68845 (18) | 0.0346 (3) | |
C4 | 0.2511 (3) | 0.19048 (10) | 0.6194 (3) | 0.0596 (5) | |
H4 | 0.1211 | 0.1785 | 0.6198 | 0.071* | |
C5 | 0.2781 (4) | 0.24283 (12) | 0.5495 (3) | 0.0764 (8) | |
H5 | 0.1657 | 0.2657 | 0.5034 | 0.092* | |
C6 | 0.4668 (4) | 0.26094 (10) | 0.5478 (3) | 0.0654 (6) | |
H6 | 0.4833 | 0.2961 | 0.5010 | 0.078* | |
C7 | 0.6340 (4) | 0.22726 (9) | 0.6155 (3) | 0.0556 (5) | |
H7 | 0.7632 | 0.2396 | 0.6139 | 0.067* | |
C8 | 0.6094 (3) | 0.17481 (8) | 0.6861 (2) | 0.0441 (4) | |
H8 | 0.7225 | 0.1522 | 0.7319 | 0.053* | |
C9 | 0.5208 (3) | 0.09950 (7) | 0.99290 (19) | 0.0370 (3) | |
C10 | 0.4178 (4) | 0.12622 (9) | 1.0923 (2) | 0.0537 (5) | |
H10 | 0.2815 | 0.1361 | 1.0528 | 0.064* | |
C11 | 0.5170 (5) | 0.13810 (11) | 1.2489 (3) | 0.0673 (6) | |
H11 | 0.4480 | 0.1563 | 1.3143 | 0.081* | |
C12 | 0.7179 (4) | 0.12315 (11) | 1.3083 (2) | 0.0656 (6) | |
H12 | 0.7848 | 0.1316 | 1.4136 | 0.079* | |
C13 | 0.8205 (4) | 0.09569 (11) | 1.2129 (3) | 0.0622 (6) | |
H13 | 0.9555 | 0.0848 | 1.2545 | 0.075* | |
C14 | 0.7225 (3) | 0.08415 (9) | 1.0540 (2) | 0.0493 (4) | |
H14 | 0.7926 | 0.0661 | 0.9891 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.03160 (12) | 0.06429 (16) | 0.07864 (18) | −0.00125 (8) | 0.02085 (10) | −0.00268 (10) |
P1 | 0.0290 (2) | 0.0349 (2) | 0.0334 (2) | 0.00300 (15) | 0.01066 (15) | −0.00370 (16) |
C1 | 0.0355 (8) | 0.0390 (8) | 0.0359 (8) | 0.0025 (7) | 0.0101 (6) | −0.0074 (7) |
C2 | 0.0320 (7) | 0.0349 (8) | 0.0366 (8) | 0.0037 (6) | 0.0096 (6) | −0.0056 (6) |
C3 | 0.0395 (9) | 0.0350 (7) | 0.0297 (7) | 0.0038 (6) | 0.0100 (6) | −0.0036 (6) |
C4 | 0.0469 (11) | 0.0609 (12) | 0.0718 (14) | 0.0138 (10) | 0.0173 (10) | 0.0199 (11) |
C5 | 0.0756 (17) | 0.0654 (15) | 0.0892 (18) | 0.0292 (13) | 0.0238 (14) | 0.0338 (14) |
C6 | 0.0874 (18) | 0.0433 (11) | 0.0666 (14) | 0.0038 (11) | 0.0226 (13) | 0.0134 (10) |
C7 | 0.0620 (13) | 0.0463 (10) | 0.0581 (12) | −0.0110 (9) | 0.0152 (10) | 0.0003 (9) |
C8 | 0.0437 (10) | 0.0398 (9) | 0.0467 (10) | −0.0006 (7) | 0.0082 (8) | 0.0000 (7) |
C9 | 0.0469 (9) | 0.0351 (8) | 0.0307 (7) | 0.0024 (7) | 0.0129 (7) | −0.0006 (6) |
C10 | 0.0656 (13) | 0.0570 (11) | 0.0416 (10) | 0.0154 (10) | 0.0197 (9) | −0.0058 (9) |
C11 | 0.100 (2) | 0.0645 (14) | 0.0425 (11) | 0.0111 (13) | 0.0283 (12) | −0.0102 (9) |
C12 | 0.0934 (19) | 0.0648 (13) | 0.0335 (10) | −0.0023 (13) | 0.0082 (10) | −0.0066 (9) |
C13 | 0.0617 (13) | 0.0720 (14) | 0.0440 (11) | 0.0025 (11) | −0.0020 (9) | −0.0014 (10) |
C14 | 0.0485 (11) | 0.0595 (11) | 0.0384 (9) | 0.0059 (9) | 0.0090 (8) | −0.0045 (8) |
Se1—P1 | 2.1055 (5) | C6—C7 | 1.378 (3) |
P1—C2 | 1.8149 (16) | C6—H6 | 0.9300 |
P1—C9 | 1.8166 (17) | C7—C8 | 1.391 (3) |
P1—C3 | 1.8244 (17) | C7—H7 | 0.9300 |
C1—C2 | 1.527 (2) | C8—H8 | 0.9300 |
C1—C1i | 1.532 (3) | C9—C14 | 1.383 (3) |
C1—H1A | 0.9700 | C9—C10 | 1.396 (2) |
C1—H1B | 0.9700 | C10—C11 | 1.379 (3) |
C2—H2A | 0.9700 | C10—H10 | 0.9300 |
C2—H2B | 0.9700 | C11—C12 | 1.374 (4) |
C3—C8 | 1.385 (3) | C11—H11 | 0.9300 |
C3—C4 | 1.386 (3) | C12—C13 | 1.375 (3) |
C4—C5 | 1.390 (3) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—C14 | 1.393 (3) |
C5—C6 | 1.358 (4) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C2—P1—C9 | 106.49 (8) | C5—C6—C7 | 120.0 (2) |
C2—P1—C3 | 106.15 (8) | C5—C6—H6 | 120.0 |
C9—P1—C3 | 104.10 (7) | C7—C6—H6 | 120.0 |
C2—P1—Se1 | 113.35 (6) | C6—C7—C8 | 120.0 (2) |
C9—P1—Se1 | 113.35 (6) | C6—C7—H7 | 120.0 |
C3—P1—Se1 | 112.67 (6) | C8—C7—H7 | 120.0 |
C2—C1—C1i | 111.36 (17) | C3—C8—C7 | 120.32 (18) |
C2—C1—H1A | 109.4 | C3—C8—H8 | 119.8 |
C1i—C1—H1A | 109.4 | C7—C8—H8 | 119.8 |
C2—C1—H1B | 109.4 | C14—C9—C10 | 119.25 (17) |
C1i—C1—H1B | 109.4 | C14—C9—P1 | 122.82 (13) |
H1A—C1—H1B | 108.0 | C10—C9—P1 | 117.90 (15) |
C1—C2—P1 | 113.40 (11) | C11—C10—C9 | 120.3 (2) |
C1—C2—H2A | 108.9 | C11—C10—H10 | 119.8 |
P1—C2—H2A | 108.9 | C9—C10—H10 | 119.8 |
C1—C2—H2B | 108.9 | C12—C11—C10 | 120.0 (2) |
P1—C2—H2B | 108.9 | C12—C11—H11 | 120.0 |
H2A—C2—H2B | 107.7 | C10—C11—H11 | 120.0 |
C8—C3—C4 | 118.85 (17) | C11—C12—C13 | 120.4 (2) |
C8—C3—P1 | 120.73 (13) | C11—C12—H12 | 119.8 |
C4—C3—P1 | 120.40 (15) | C13—C12—H12 | 119.8 |
C3—C4—C5 | 120.2 (2) | C12—C13—C14 | 120.0 (2) |
C3—C4—H4 | 119.9 | C12—C13—H13 | 120.0 |
C5—C4—H4 | 119.9 | C14—C13—H13 | 120.0 |
C6—C5—C4 | 120.6 (2) | C9—C14—C13 | 119.93 (19) |
C6—C5—H5 | 119.7 | C9—C14—H14 | 120.0 |
C4—C5—H5 | 119.7 | C13—C14—H14 | 120.0 |
C1i—C1—C2—P1 | 173.67 (15) | P1—C3—C8—C7 | −178.28 (15) |
C9—P1—C2—C1 | −178.94 (12) | C6—C7—C8—C3 | 0.2 (3) |
C3—P1—C2—C1 | −68.45 (14) | C2—P1—C9—C14 | 19.60 (18) |
Se1—P1—C2—C1 | 55.75 (13) | C3—P1—C9—C14 | −92.32 (17) |
C2—P1—C3—C8 | −50.30 (15) | Se1—P1—C9—C14 | 144.91 (15) |
C9—P1—C3—C8 | 61.88 (15) | C2—P1—C9—C10 | −162.27 (15) |
Se1—P1—C3—C8 | −174.91 (12) | C3—P1—C9—C10 | 85.81 (16) |
C2—P1—C3—C4 | 131.43 (16) | Se1—P1—C9—C10 | −36.96 (17) |
C9—P1—C3—C4 | −116.39 (17) | C14—C9—C10—C11 | 1.1 (3) |
Se1—P1—C3—C4 | 6.82 (18) | P1—C9—C10—C11 | −177.05 (18) |
C8—C3—C4—C5 | −0.1 (3) | C9—C10—C11—C12 | −0.6 (4) |
P1—C3—C4—C5 | 178.2 (2) | C10—C11—C12—C13 | −0.8 (4) |
C3—C4—C5—C6 | 0.0 (4) | C11—C12—C13—C14 | 1.6 (4) |
C4—C5—C6—C7 | 0.2 (4) | C10—C9—C14—C13 | −0.3 (3) |
C5—C6—C7—C8 | −0.3 (4) | P1—C9—C14—C13 | 177.79 (18) |
C4—C3—C8—C7 | 0.0 (3) | C12—C13—C14—C9 | −1.1 (4) |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C28H28P2Se2 |
Mr | 584.36 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 6.8206 (7), 23.154 (3), 8.7018 (9) |
β (°) | 105.380 (2) |
V (Å3) | 1325.0 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.93 |
Crystal size (mm) | 0.60 × 0.25 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996; Blessing, 1995) |
Tmin, Tmax | 0.382, 0.570 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11599, 3080, 2741 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.666 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.075, 1.02 |
No. of reflections | 3080 |
No. of parameters | 145 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.41 |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT and XPREP (Siemens, 1995), SIR97 (Altomare et al., 1997), SHELXL97 (Sheldrick, 1997), TEXSAN for Windows (Molecular Structure Corporation, 1997).
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Tertiary phosphine chalcogenides have been reported to be versatile coordinating agents and have shown extraction and catalytic behaviour (Lobana, 1989). There have been few structural accounts of tertiary phosphine selenides or their complexes; Ph3PSe (Codding & Kerr, 1979), HgCl2(Ph3PSe) as a chloro-bridged dimer (Glasser et al., 1969), AuCl(Ph3PSe) (Hussain, 1986), CuI(Ph3PSe)(CH3CN) as an iodo-bridged dimer (Lobana et al., 1999), ZnI2(dppmSe2) [where dppmSe2 is 1,1-methylenebis(diphenylphosphine selenide); Lobana, Hundal & Turner, 2001] and CuCl(dppeSe2) as a chloro- and dppeSe2-bridged dimer [where dppeSe2 is 1,2-ethylenebis(diphenylphosphine selenide); Lobana, Mahajan & Castineiras, 2001].
As part of an ongoing study of the structural chemistry of phosphine selenide ligands and their complexes, we have prepared and obtained single crystals of the title compound, (I) (Fig. 1).