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The title compound, C28H28P2Se2, is located on an inversion centre. The Se-P bond length is 2.1055 (5) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800018754/ob6003sup1.cif
Contains datablocks I, tsl4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800018754/ob6003Isup2.hkl
Contains datablock I

CCDC reference: 155876

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](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


Yellow Alert 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

Comment top

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).

Experimental top

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).

Refinement top

Crystal decay was assessed with a recollection the first 182 reflections at the end of the experiment.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976; Hall et al., 1999) projection of (I) with displacement ellipsoids shown at the 20% probability level.
(I) top
Crystal data top
C28H28P2Se2F(000) = 588
Mr = 584.36Dx = 1.465 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.8206 (7) ÅCell parameters from 918 reflections
b = 23.154 (3) Åθ = 2.6–27.7°
c = 8.7018 (9) ŵ = 2.93 mm1
β = 105.380 (2)°T = 294 K
V = 1325.0 (2) Å3Prism, colourless
Z = 20.60 × 0.25 × 0.19 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
3080 independent reflections
Radiation source: sealed tube2741 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 98
Tmin = 0.382, Tmax = 0.570k = 3030
11599 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-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 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
C28H28P2Se2V = 1325.0 (2) Å3
Mr = 584.36Z = 2
Monoclinic, P21/nMo Kα radiation
a = 6.8206 (7) ŵ = 2.93 mm1
b = 23.154 (3) ÅT = 294 K
c = 8.7018 (9) Å0.60 × 0.25 × 0.19 mm
β = 105.380 (2)°
Data collection top
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 = 0.570Rint = 0.017
11599 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.075H-atom parameters constrained
S = 1.02Δρmax = 0.47 e Å3
3080 reflectionsΔρmin = 0.41 e Å3
145 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. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Se10.07579 (3)0.066872 (10)0.75371 (3)0.05699 (10)
P10.38395 (6)0.088362 (18)0.78555 (5)0.03200 (10)
C10.4317 (3)0.02035 (7)0.53219 (19)0.0367 (3)
H1A0.41190.05590.47110.044*
H1B0.29970.00250.51940.044*
C20.5248 (2)0.03422 (7)0.70804 (19)0.0344 (3)
H2A0.66300.04780.72180.041*
H2B0.53110.00090.76980.041*
C30.4174 (3)0.15610 (7)0.68845 (18)0.0346 (3)
C40.2511 (3)0.19048 (10)0.6194 (3)0.0596 (5)
H40.12110.17850.61980.071*
C50.2781 (4)0.24283 (12)0.5495 (3)0.0764 (8)
H50.16570.26570.50340.092*
C60.4668 (4)0.26094 (10)0.5478 (3)0.0654 (6)
H60.48330.29610.50100.078*
C70.6340 (4)0.22726 (9)0.6155 (3)0.0556 (5)
H70.76320.23960.61390.067*
C80.6094 (3)0.17481 (8)0.6861 (2)0.0441 (4)
H80.72250.15220.73190.053*
C90.5208 (3)0.09950 (7)0.99290 (19)0.0370 (3)
C100.4178 (4)0.12622 (9)1.0923 (2)0.0537 (5)
H100.28150.13611.05280.064*
C110.5170 (5)0.13810 (11)1.2489 (3)0.0673 (6)
H110.44800.15631.31430.081*
C120.7179 (4)0.12315 (11)1.3083 (2)0.0656 (6)
H120.78480.13161.41360.079*
C130.8205 (4)0.09569 (11)1.2129 (3)0.0622 (6)
H130.95550.08481.25450.075*
C140.7225 (3)0.08415 (9)1.0540 (2)0.0493 (4)
H140.79260.06610.98910.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.03160 (12)0.06429 (16)0.07864 (18)0.00125 (8)0.02085 (10)0.00268 (10)
P10.0290 (2)0.0349 (2)0.0334 (2)0.00300 (15)0.01066 (15)0.00370 (16)
C10.0355 (8)0.0390 (8)0.0359 (8)0.0025 (7)0.0101 (6)0.0074 (7)
C20.0320 (7)0.0349 (8)0.0366 (8)0.0037 (6)0.0096 (6)0.0056 (6)
C30.0395 (9)0.0350 (7)0.0297 (7)0.0038 (6)0.0100 (6)0.0036 (6)
C40.0469 (11)0.0609 (12)0.0718 (14)0.0138 (10)0.0173 (10)0.0199 (11)
C50.0756 (17)0.0654 (15)0.0892 (18)0.0292 (13)0.0238 (14)0.0338 (14)
C60.0874 (18)0.0433 (11)0.0666 (14)0.0038 (11)0.0226 (13)0.0134 (10)
C70.0620 (13)0.0463 (10)0.0581 (12)0.0110 (9)0.0152 (10)0.0003 (9)
C80.0437 (10)0.0398 (9)0.0467 (10)0.0006 (7)0.0082 (8)0.0000 (7)
C90.0469 (9)0.0351 (8)0.0307 (7)0.0024 (7)0.0129 (7)0.0006 (6)
C100.0656 (13)0.0570 (11)0.0416 (10)0.0154 (10)0.0197 (9)0.0058 (9)
C110.100 (2)0.0645 (14)0.0425 (11)0.0111 (13)0.0283 (12)0.0102 (9)
C120.0934 (19)0.0648 (13)0.0335 (10)0.0023 (13)0.0082 (10)0.0066 (9)
C130.0617 (13)0.0720 (14)0.0440 (11)0.0025 (11)0.0020 (9)0.0014 (10)
C140.0485 (11)0.0595 (11)0.0384 (9)0.0059 (9)0.0090 (8)0.0045 (8)
Geometric parameters (Å, º) top
Se1—P12.1055 (5)C6—C71.378 (3)
P1—C21.8149 (16)C6—H60.9300
P1—C91.8166 (17)C7—C81.391 (3)
P1—C31.8244 (17)C7—H70.9300
C1—C21.527 (2)C8—H80.9300
C1—C1i1.532 (3)C9—C141.383 (3)
C1—H1A0.9700C9—C101.396 (2)
C1—H1B0.9700C10—C111.379 (3)
C2—H2A0.9700C10—H100.9300
C2—H2B0.9700C11—C121.374 (4)
C3—C81.385 (3)C11—H110.9300
C3—C41.386 (3)C12—C131.375 (3)
C4—C51.390 (3)C12—H120.9300
C4—H40.9300C13—C141.393 (3)
C5—C61.358 (4)C13—H130.9300
C5—H50.9300C14—H140.9300
C2—P1—C9106.49 (8)C5—C6—C7120.0 (2)
C2—P1—C3106.15 (8)C5—C6—H6120.0
C9—P1—C3104.10 (7)C7—C6—H6120.0
C2—P1—Se1113.35 (6)C6—C7—C8120.0 (2)
C9—P1—Se1113.35 (6)C6—C7—H7120.0
C3—P1—Se1112.67 (6)C8—C7—H7120.0
C2—C1—C1i111.36 (17)C3—C8—C7120.32 (18)
C2—C1—H1A109.4C3—C8—H8119.8
C1i—C1—H1A109.4C7—C8—H8119.8
C2—C1—H1B109.4C14—C9—C10119.25 (17)
C1i—C1—H1B109.4C14—C9—P1122.82 (13)
H1A—C1—H1B108.0C10—C9—P1117.90 (15)
C1—C2—P1113.40 (11)C11—C10—C9120.3 (2)
C1—C2—H2A108.9C11—C10—H10119.8
P1—C2—H2A108.9C9—C10—H10119.8
C1—C2—H2B108.9C12—C11—C10120.0 (2)
P1—C2—H2B108.9C12—C11—H11120.0
H2A—C2—H2B107.7C10—C11—H11120.0
C8—C3—C4118.85 (17)C11—C12—C13120.4 (2)
C8—C3—P1120.73 (13)C11—C12—H12119.8
C4—C3—P1120.40 (15)C13—C12—H12119.8
C3—C4—C5120.2 (2)C12—C13—C14120.0 (2)
C3—C4—H4119.9C12—C13—H13120.0
C5—C4—H4119.9C14—C13—H13120.0
C6—C5—C4120.6 (2)C9—C14—C13119.93 (19)
C6—C5—H5119.7C9—C14—H14120.0
C4—C5—H5119.7C13—C14—H14120.0
C1i—C1—C2—P1173.67 (15)P1—C3—C8—C7178.28 (15)
C9—P1—C2—C1178.94 (12)C6—C7—C8—C30.2 (3)
C3—P1—C2—C168.45 (14)C2—P1—C9—C1419.60 (18)
Se1—P1—C2—C155.75 (13)C3—P1—C9—C1492.32 (17)
C2—P1—C3—C850.30 (15)Se1—P1—C9—C14144.91 (15)
C9—P1—C3—C861.88 (15)C2—P1—C9—C10162.27 (15)
Se1—P1—C3—C8174.91 (12)C3—P1—C9—C1085.81 (16)
C2—P1—C3—C4131.43 (16)Se1—P1—C9—C1036.96 (17)
C9—P1—C3—C4116.39 (17)C14—C9—C10—C111.1 (3)
Se1—P1—C3—C46.82 (18)P1—C9—C10—C11177.05 (18)
C8—C3—C4—C50.1 (3)C9—C10—C11—C120.6 (4)
P1—C3—C4—C5178.2 (2)C10—C11—C12—C130.8 (4)
C3—C4—C5—C60.0 (4)C11—C12—C13—C141.6 (4)
C4—C5—C6—C70.2 (4)C10—C9—C14—C130.3 (3)
C5—C6—C7—C80.3 (4)P1—C9—C14—C13177.79 (18)
C4—C3—C8—C70.0 (3)C12—C13—C14—C91.1 (4)
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC28H28P2Se2
Mr584.36
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)6.8206 (7), 23.154 (3), 8.7018 (9)
β (°) 105.380 (2)
V3)1325.0 (2)
Z2
Radiation typeMo Kα
µ (mm1)2.93
Crystal size (mm)0.60 × 0.25 × 0.19
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996; Blessing, 1995)
Tmin, Tmax0.382, 0.570
No. of measured, independent and
observed [I > 2σ(I)] reflections
11599, 3080, 2741
Rint0.017
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.075, 1.02
No. of reflections3080
No. of parameters145
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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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