organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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5-Benzyl­­idene-2,3-di­phenyl-1,2-selena­phosphole-2-selenide

aDepartment of Chemistry, University of St Andrews, St Andrews KY16 9ST, Scotland
*Correspondence e-mail: jdw3@st-andrews.ac.uk

(Received 15 November 2007; accepted 22 November 2007; online 6 December 2007)

The title compound, C23H19PSe2, has a central five-membered twist C3PSe ring conformation. One phenyl ring substituent, attached to an sp2 carbon, is approximately coplanar with the C3PSe ring whilst the other organic substituents, attached to an sp3-carbon and a PV atom, lie on the same side of the ring.

Related literature

For related literature, see: Yoshifuji et al. (1998[Yoshifuji, M., An, D. L., Higeta, N. & Toyota, K. (1998). Chem. Lett. pp. 17-18.]); Fitzmaurice et al. (1988[Fitzmaurice, J. C., Williams, J. C., Wood, P. T. & Woollins, J. D. (1988). J. Chem. Soc. Chem. Commun. pp. 741-743.]); Gray, Bhattacharyya et al. (2005[Gray, I. P., Bhattacharyya, P., Slawin, A. M. Z. & Woollins, J. D. (2005). Chem. Eur. J. 11, 6221-6227.]); Gray, Slawin et al. (2005[Gray, I. P., Slawin, A. M. Z. & Woollins, J. D. (2005). Dalton Trans. pp. 2188-2194.]); Hua & Woollins (2007[Hua, G. & Woollins, J. D. (2007). Tetrahedron Lett. 48, 3677-3679.]) and literature cited therein; Hua et al. (2006[Hua, G., Li, Y., Slawin, A. M. Z. & Woollins, J. D. (2006). Org. Lett. 8, 5251-5254.]); Mugesh et al. (2001[Mugesh, G., Du Mont, W.-W. & Sies, H. (2001). Chem. Rev. 101, 2125-2179.]); Shi et al. (2006[Shi, W., Shafaei-Fallah, M., Anson, C. E. & Rothenberger, A. (2006). Dalton Trans. pp. 2979-2983.], 2007[Shi, W., Shafaei-Fallah, M., Zhang, L., Anson, C. E., Matern, E. & Rothenberger, A. (2007). Chem. Eur. J. 13, 598-603.]); Sommen et al. (2005[Sommen, G. L., Linden, A. & Heimgartner, H. (2005). Helv. Chim. Acta, 88, 766-773.]).

[Scheme 1]

Experimental

Crystal data
  • C23H19PSe2

  • Mr = 484.27

  • Monoclinic, C 2/c

  • a = 22.385 (2) Å

  • b = 14.4348 (14) Å

  • c = 12.4433 (12) Å

  • β = 94.847 (2)°

  • V = 4006.4 (7) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 3.78 mm−1

  • T = 93 (2) K

  • 0.30 × 0.15 × 0.10 mm

Data collection
  • Rigaku Mercury CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku,2004[Rigaku (2004). CrystalClear. Version 1.36. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.515, Tmax = 0.692

  • 11508 measured reflections

  • 3667 independent reflections

  • 3125 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.077

  • S = 1.04

  • 3667 reflections

  • 235 parameters

  • H-atom parameters constrained

  • Δρmax = 0.95 e Å−3

  • Δρmin = −0.41 e Å−3

Table 1
Selected geometric parameters (Å, °)

Se2—C9 1.941 (3)
Se2—P1 2.2523 (9)
Se1—P1 2.1044 (9)
P1—C1 1.817 (3)
P1—C7 1.862 (3)
C8—C9 1.334 (5)
C8—C7 1.500 (5)
C9—Se2—P1 87.97 (10)
C1—P1—C7 109.16 (15)
C1—P1—Se1 112.86 (11)
C7—P1—Se1 115.65 (11)
C1—P1—Se2 105.64 (11)
C7—P1—Se2 96.47 (10)
Se1—P1—Se2 115.54 (4)
C9—C8—C7 123.3 (3)
C8—C7—P1 107.5 (2)
C8—C9—Se2 117.1 (2)

Data collection: CrystalClear (Rigaku, 2004[Rigaku (2004). CrystalClear. Version 1.36. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: Bruker SHELXTL (Sheldrick, 2003[Sheldrick, G. M. (2003). SHELXTL. Version 6.14. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: Bruker SHELXTL.

Supporting information


Comment top

Organoselenium chemistry is attracting increasing attention because of chemo-, regio-, and stereoselective reactions and useful biological activity(Mugesh et al., 2001). However, the synthesis of selenium-containing organic heterocycles can be problematic involving use of toxic selenium reagents which are often difficult to handle. 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide [PhP(Se)(µ-Se)]2, known as Woollins reagent (WR) excels in efficiency and broad utility, capable of preparing a wide range selenium-containing heterocycles and the related compounds (Gray, Bhattacharyya et al. (2005); Gray, Slawin et al. (2005); Shi et al., 2006, 2007). In our new five membered P—Se heterocycle the P = Se bond length (2.1044 (9) Å) and the P—Se distance (2.2523 (9) Å, Table 1) are consistent with the related selenides-containing PV= Se bonds (2.081 (2) - 2.123 (3) Å) and PV—Se single bonds (Fitzmaurice et al. 1988, Yoshifuji et al. 1998).

Related literature top

For related literature, see: Yoshifuji et al. (1998); Fitzmaurice et al. (1988); Gray, Bhattacharyya et al. (2005); Gray, Slawin et al. (2005); Hua & Woollins (2007) and literature cited therein; Hua et al. (2006); Mugesh et al. (2001); Shi et al. (2006, 2007); Sommen et al. (2005).

Experimental top

A mixture of dibenzoylideneacetone (0.47 g, 2 mmol) and Woollins' reagent (0.54 g, 1 mmol) in 10 ml of dry toluene was refluxed for 20 hr. The red suspension disappeared and a red solution was formed along with a small amount of elemental selenium in the bottom of flask. Upon cooling to room temperature the mixture was purified by silica gel column chromatograhy (toluene as eluent) to give the title compound in 83% yield. Colorless crystal were grown from dichloromethane with slow diffusion of n-hexane. Anal. Calcd for C23H19PSe2: C, 57.04; H, 3.95. Found: C, 57.01; H, 3.99. 1H NMR (CDCl3): 7.63–7.47 (m, 2H, ArH), 7.37–7.30 (m, 3H, ArH), 7.21–7.12 (m, 4H, ArH), 7.11–7.04 (m, 4H, AeH), 6.96–6.93 (m, 2H, ArH), 7.05 (d, 1H, CH=CH), 6.95 (d, 1H, CH=CH), 6.66 (dd, 1H, CH=CH), 6.36 (dd, 1H, CH=CH). 31P NMR (CDCl3): 69.85 (s, J(P,Seendo) = 350 Hz, J(P,Seexo) = 782 Hz). 77Se NMR (CDCl3): 354.85 (J(P,Seendo) = 350 Hz), -169.99 (J(P,Seexo) = 780 Hz).

Refinement top

All H atoms were included in calculated positions (C—H distances are 0.98 Å for methyl H atoms, 0.99 Å for methylene H atoms and 0.95 Å for aryl H atoms) and were refined as riding atoms with Uiso(H) = 1.2 Ueq (parent atom, methylene and aryl H atoms) or Uiso(H) = 1.5 Ueq (parent atom,methyl H atoms).

Structure description top

Organoselenium chemistry is attracting increasing attention because of chemo-, regio-, and stereoselective reactions and useful biological activity(Mugesh et al., 2001). However, the synthesis of selenium-containing organic heterocycles can be problematic involving use of toxic selenium reagents which are often difficult to handle. 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide [PhP(Se)(µ-Se)]2, known as Woollins reagent (WR) excels in efficiency and broad utility, capable of preparing a wide range selenium-containing heterocycles and the related compounds (Gray, Bhattacharyya et al. (2005); Gray, Slawin et al. (2005); Shi et al., 2006, 2007). In our new five membered P—Se heterocycle the P = Se bond length (2.1044 (9) Å) and the P—Se distance (2.2523 (9) Å, Table 1) are consistent with the related selenides-containing PV= Se bonds (2.081 (2) - 2.123 (3) Å) and PV—Se single bonds (Fitzmaurice et al. 1988, Yoshifuji et al. 1998).

For related literature, see: Yoshifuji et al. (1998); Fitzmaurice et al. (1988); Gray, Bhattacharyya et al. (2005); Gray, Slawin et al. (2005); Hua & Woollins (2007) and literature cited therein; Hua et al. (2006); Mugesh et al. (2001); Shi et al. (2006, 2007); Sommen et al. (2005).

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear (Rigaku, 2004); data reduction: CrystalClear (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL (Sheldrick,2003); software used to prepare material for publication: Bruker SHELXTL (Sheldrick,2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
5-Benzylidene-2,3-diphenyl-1,2-selenaphosphole-2-selenide top
Crystal data top
C23H19PSe2F(000) = 1920
Mr = 484.27Dx = 1.606 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8628 reflections
a = 22.385 (2) Åθ = 1.6–25.3°
b = 14.4348 (14) ŵ = 3.78 mm1
c = 12.4433 (12) ÅT = 93 K
β = 94.847 (2)°Prism, colorless
V = 4006.4 (7) Å30.30 × 0.15 × 0.10 mm
Z = 8
Data collection top
Rigaku Mercury CCD
diffractometer
3667 independent reflections
Radiation source: rotating anode3125 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.043
ω and φ scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan
(CrystalClear; Rigaku,2004)
h = 2617
Tmin = 0.515, Tmax = 0.692k = 1818
11508 measured reflectionsl = 1515
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.032P)2 + 14.4806P]
where P = (Fo2 + 2Fc2)/3
3667 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.95 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
C23H19PSe2V = 4006.4 (7) Å3
Mr = 484.27Z = 8
Monoclinic, C2/cMo Kα radiation
a = 22.385 (2) ŵ = 3.78 mm1
b = 14.4348 (14) ÅT = 93 K
c = 12.4433 (12) Å0.30 × 0.15 × 0.10 mm
β = 94.847 (2)°
Data collection top
Rigaku Mercury CCD
diffractometer
3667 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku,2004)
3125 reflections with I > 2σ(I)
Tmin = 0.515, Tmax = 0.692Rint = 0.043
11508 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.077H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.032P)2 + 14.4806P]
where P = (Fo2 + 2Fc2)/3
3667 reflectionsΔρmax = 0.95 e Å3
235 parametersΔρmin = 0.41 e Å3
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
xyzUiso*/Ueq
Se20.946290 (15)0.03631 (2)0.57968 (3)0.02008 (10)
Se10.960236 (16)0.21801 (2)0.57205 (3)0.02484 (11)
P10.90715 (4)0.10413 (6)0.60975 (7)0.01702 (19)
C190.93533 (15)0.4014 (2)0.5818 (3)0.0236 (8)
H190.94260.37430.51450.028*
C60.81730 (16)0.1775 (2)0.4664 (3)0.0237 (8)
H60.84390.22810.46000.028*
C100.85050 (14)0.1485 (2)0.7960 (2)0.0182 (7)
C20.79343 (16)0.0315 (2)0.5460 (3)0.0254 (8)
H20.80420.01880.59310.030*
C110.79206 (15)0.1186 (3)0.8016 (3)0.0240 (8)
H110.78130.05730.78000.029*
C50.76207 (17)0.1763 (3)0.4063 (3)0.0326 (9)
H50.75150.22530.35730.039*
C130.76399 (17)0.2669 (3)0.8696 (3)0.0286 (9)
H130.73460.30720.89450.034*
C10.83355 (14)0.1048 (2)0.5360 (3)0.0188 (7)
C150.86516 (16)0.2385 (2)0.8277 (3)0.0245 (8)
H150.90500.26020.82450.029*
C220.91438 (18)0.4819 (3)0.7761 (3)0.0326 (9)
H220.90700.50960.84300.039*
C180.92438 (14)0.3447 (2)0.6681 (3)0.0201 (7)
C30.73807 (17)0.0323 (3)0.4872 (3)0.0330 (9)
H30.71060.01690.49490.040*
C120.74889 (16)0.1772 (3)0.8384 (3)0.0294 (8)
H120.70900.15560.84220.035*
C40.72257 (18)0.1045 (3)0.4173 (3)0.0349 (9)
H40.68460.10460.37690.042*
C80.89178 (15)0.0157 (2)0.7738 (2)0.0202 (7)
H80.87290.03570.83540.024*
C140.82195 (17)0.2971 (3)0.8641 (3)0.0299 (9)
H140.83250.35860.88540.036*
C210.92538 (16)0.5374 (2)0.6896 (3)0.0294 (8)
H210.92580.60290.69710.035*
C160.90956 (15)0.1790 (2)0.7240 (3)0.0216 (7)
H160.89660.20030.79040.026*
C70.89842 (15)0.0864 (2)0.7559 (3)0.0186 (7)
H70.93720.10520.79550.022*
C230.91395 (17)0.3864 (3)0.7666 (3)0.0274 (8)
H230.90660.34900.82690.033*
C170.92483 (14)0.2435 (2)0.6540 (3)0.0196 (7)
H170.93740.22140.58760.024*
C90.91106 (14)0.0799 (2)0.7077 (3)0.0185 (7)
C200.93580 (16)0.4975 (3)0.5923 (3)0.0292 (8)
H200.94330.53540.53250.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se20.02552 (19)0.01480 (18)0.02139 (18)0.00227 (13)0.01059 (13)0.00242 (14)
Se10.0290 (2)0.01641 (18)0.0306 (2)0.00455 (14)0.01166 (15)0.00100 (15)
P10.0214 (4)0.0136 (4)0.0169 (4)0.0008 (3)0.0065 (3)0.0003 (3)
C190.0256 (19)0.0207 (18)0.0248 (19)0.0015 (14)0.0034 (14)0.0006 (15)
C60.0312 (19)0.0211 (18)0.0200 (18)0.0048 (15)0.0083 (14)0.0030 (15)
C100.0246 (18)0.0223 (18)0.0078 (15)0.0015 (14)0.0013 (12)0.0015 (14)
C20.032 (2)0.0220 (18)0.0214 (18)0.0023 (15)0.0003 (14)0.0039 (16)
C110.0277 (19)0.0263 (19)0.0190 (18)0.0022 (15)0.0076 (14)0.0020 (15)
C50.041 (2)0.036 (2)0.0207 (19)0.0131 (18)0.0013 (16)0.0044 (17)
C130.036 (2)0.032 (2)0.0183 (18)0.0138 (17)0.0096 (15)0.0010 (16)
C10.0226 (17)0.0199 (17)0.0142 (16)0.0005 (14)0.0039 (13)0.0046 (14)
C150.0289 (19)0.0238 (19)0.0208 (18)0.0001 (15)0.0018 (14)0.0012 (15)
C220.048 (2)0.023 (2)0.026 (2)0.0017 (17)0.0025 (17)0.0092 (17)
C180.0152 (16)0.0176 (17)0.0272 (19)0.0003 (13)0.0010 (13)0.0009 (15)
C30.032 (2)0.039 (2)0.028 (2)0.0071 (18)0.0020 (16)0.0057 (19)
C120.0220 (18)0.042 (2)0.0252 (19)0.0006 (16)0.0071 (14)0.0067 (17)
C40.034 (2)0.046 (3)0.023 (2)0.0075 (19)0.0058 (16)0.0061 (19)
C80.0263 (18)0.0233 (19)0.0114 (16)0.0011 (14)0.0036 (13)0.0018 (14)
C140.042 (2)0.022 (2)0.026 (2)0.0046 (16)0.0036 (16)0.0053 (17)
C210.031 (2)0.0151 (18)0.040 (2)0.0019 (15)0.0068 (16)0.0023 (17)
C160.0279 (19)0.0191 (17)0.0183 (17)0.0011 (14)0.0035 (14)0.0067 (14)
C70.0214 (17)0.0181 (17)0.0164 (17)0.0001 (13)0.0029 (13)0.0022 (14)
C230.038 (2)0.0219 (19)0.0219 (19)0.0003 (16)0.0006 (15)0.0008 (16)
C170.0195 (17)0.0192 (17)0.0204 (17)0.0013 (13)0.0031 (13)0.0034 (14)
C90.0205 (17)0.0190 (17)0.0159 (17)0.0007 (13)0.0013 (13)0.0029 (14)
C200.031 (2)0.0215 (19)0.036 (2)0.0027 (15)0.0029 (16)0.0058 (17)
Geometric parameters (Å, º) top
Se2—C91.941 (3)C15—C141.389 (5)
Se2—P12.2523 (9)C15—H150.9500
Se1—P12.1044 (9)C22—C211.381 (5)
P1—C11.817 (3)C22—C231.383 (5)
P1—C71.862 (3)C22—H220.9500
C19—C181.389 (5)C18—C231.402 (5)
C19—C201.393 (5)C18—C171.472 (5)
C19—H190.9500C3—C41.383 (6)
C6—C51.390 (5)C3—H30.9500
C6—C11.390 (5)C12—H120.9500
C6—H60.9500C4—H40.9500
C10—C111.385 (5)C8—C91.334 (5)
C10—C151.389 (5)C8—C71.500 (5)
C10—C71.515 (4)C8—H80.9500
C2—C31.385 (5)C14—H140.9500
C2—C11.400 (5)C21—C201.378 (5)
C2—H20.9500C21—H210.9500
C11—C121.390 (5)C16—C171.339 (5)
C11—H110.9500C16—C91.446 (5)
C5—C41.377 (6)C16—H160.9500
C5—H50.9500C7—H71.0000
C13—C141.376 (5)C23—H230.9500
C13—C121.385 (5)C17—H170.9500
C13—H130.9500C20—H200.9500
C9—Se2—P187.97 (10)C4—C3—C2120.3 (4)
C1—P1—C7109.16 (15)C4—C3—H3119.8
C1—P1—Se1112.86 (11)C2—C3—H3119.8
C7—P1—Se1115.65 (11)C13—C12—C11120.0 (3)
C1—P1—Se2105.64 (11)C13—C12—H12120.0
C7—P1—Se296.47 (10)C11—C12—H12120.0
Se1—P1—Se2115.54 (4)C5—C4—C3120.1 (4)
C18—C19—C20120.9 (3)C5—C4—H4120.0
C18—C19—H19119.5C3—C4—H4120.0
C20—C19—H19119.5C9—C8—C7123.3 (3)
C5—C6—C1120.0 (3)C9—C8—H8118.4
C5—C6—H6120.0C7—C8—H8118.4
C1—C6—H6120.0C13—C14—C15120.6 (3)
C11—C10—C15118.6 (3)C13—C14—H14119.7
C11—C10—C7122.0 (3)C15—C14—H14119.7
C15—C10—C7119.4 (3)C20—C21—C22119.7 (3)
C3—C2—C1119.9 (3)C20—C21—H21120.1
C3—C2—H2120.1C22—C21—H21120.1
C1—C2—H2120.1C17—C16—C9125.9 (3)
C10—C11—C12120.9 (3)C17—C16—H16117.1
C10—C11—H11119.6C9—C16—H16117.1
C12—C11—H11119.6C8—C7—C10116.8 (3)
C4—C5—C6120.3 (4)C8—C7—P1107.5 (2)
C4—C5—H5119.8C10—C7—P1112.1 (2)
C6—C5—H5119.8C8—C7—H7106.6
C14—C13—C12119.4 (3)C10—C7—H7106.6
C14—C13—H13120.3P1—C7—H7106.6
C12—C13—H13120.3C22—C23—C18120.2 (3)
C6—C1—C2119.4 (3)C22—C23—H23119.9
C6—C1—P1119.8 (3)C18—C23—H23119.9
C2—C1—P1120.8 (3)C16—C17—C18127.4 (3)
C14—C15—C10120.5 (3)C16—C17—H17116.3
C14—C15—H15119.7C18—C17—H17116.3
C10—C15—H15119.7C8—C9—C16126.0 (3)
C21—C22—C23120.8 (3)C8—C9—Se2117.1 (2)
C21—C22—H22119.6C16—C9—Se2116.8 (2)
C23—C22—H22119.6C21—C20—C19119.9 (3)
C19—C18—C23118.4 (3)C21—C20—H20120.0
C19—C18—C17119.3 (3)C19—C20—H20120.0
C23—C18—C17122.3 (3)
C9—Se2—P1—C190.70 (14)C23—C22—C21—C200.3 (6)
C9—Se2—P1—C721.31 (14)C9—C8—C7—C10149.3 (3)
C9—Se2—P1—Se1143.79 (10)C9—C8—C7—P122.4 (4)
C15—C10—C11—C120.2 (5)C11—C10—C7—C829.5 (4)
C7—C10—C11—C12179.8 (3)C15—C10—C7—C8150.9 (3)
C1—C6—C5—C41.7 (5)C11—C10—C7—P195.1 (3)
C5—C6—C1—C21.0 (5)C15—C10—C7—P184.5 (3)
C5—C6—C1—P1177.2 (3)C1—P1—C7—C882.6 (2)
C3—C2—C1—C60.3 (5)Se1—P1—C7—C8148.82 (19)
C3—C2—C1—P1178.5 (3)Se2—P1—C7—C826.4 (2)
C7—P1—C1—C6128.1 (3)C1—P1—C7—C1047.0 (3)
Se1—P1—C1—C62.0 (3)Se1—P1—C7—C1081.5 (2)
Se2—P1—C1—C6129.2 (2)Se2—P1—C7—C10156.1 (2)
C7—P1—C1—C253.7 (3)C21—C22—C23—C180.4 (6)
Se1—P1—C1—C2176.2 (2)C19—C18—C23—C220.3 (5)
Se2—P1—C1—C249.1 (3)C17—C18—C23—C22179.6 (3)
C11—C10—C15—C140.1 (5)C9—C16—C17—C18179.4 (3)
C7—C10—C15—C14179.6 (3)C19—C18—C17—C16172.9 (3)
C20—C19—C18—C230.2 (5)C23—C18—C17—C167.9 (5)
C20—C19—C18—C17179.4 (3)C7—C8—C9—C16175.7 (3)
C1—C2—C3—C41.0 (5)C7—C8—C9—Se22.5 (4)
C14—C13—C12—C110.3 (5)C17—C16—C9—C8174.8 (3)
C10—C11—C12—C130.3 (5)C17—C16—C9—Se26.9 (5)
C6—C5—C4—C31.0 (6)P1—Se2—C9—C814.4 (3)
C2—C3—C4—C50.4 (6)P1—Se2—C9—C16167.2 (3)
C12—C13—C14—C150.0 (5)C22—C21—C20—C190.2 (5)
C10—C15—C14—C130.2 (5)C18—C19—C20—C210.1 (5)

Experimental details

Crystal data
Chemical formulaC23H19PSe2
Mr484.27
Crystal system, space groupMonoclinic, C2/c
Temperature (K)93
a, b, c (Å)22.385 (2), 14.4348 (14), 12.4433 (12)
β (°) 94.847 (2)
V3)4006.4 (7)
Z8
Radiation typeMo Kα
µ (mm1)3.78
Crystal size (mm)0.30 × 0.15 × 0.10
Data collection
DiffractometerRigaku Mercury CCD
Absorption correctionMulti-scan
(CrystalClear; Rigaku,2004)
Tmin, Tmax0.515, 0.692
No. of measured, independent and
observed [I > 2σ(I)] reflections
11508, 3667, 3125
Rint0.043
(sin θ/λ)max1)0.607
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.077, 1.04
No. of reflections3667
No. of parameters235
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.032P)2 + 14.4806P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.95, 0.41

Computer programs: CrystalClear (Rigaku, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), Bruker SHELXTL (Sheldrick,2003).

Selected geometric parameters (Å, º) top
Se2—C91.941 (3)P1—C71.862 (3)
Se2—P12.2523 (9)C8—C91.334 (5)
Se1—P12.1044 (9)C8—C71.500 (5)
P1—C11.817 (3)
C9—Se2—P187.97 (10)C7—P1—Se296.47 (10)
C1—P1—C7109.16 (15)Se1—P1—Se2115.54 (4)
C1—P1—Se1112.86 (11)C9—C8—C7123.3 (3)
C7—P1—Se1115.65 (11)C8—C7—P1107.5 (2)
C1—P1—Se2105.64 (11)C8—C9—Se2117.1 (2)
 

Acknowledgements

The authors are grateful to the Engineering and Physical Science Research Council (EPSRC, UK) for financial support.

References

First citationFitzmaurice, J. C., Williams, J. C., Wood, P. T. & Woollins, J. D. (1988). J. Chem. Soc. Chem. Commun. pp. 741–743.  CrossRef Web of Science Google Scholar
First citationGray, I. P., Bhattacharyya, P., Slawin, A. M. Z. & Woollins, J. D. (2005). Chem. Eur. J. 11, 6221–6227.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationGray, I. P., Slawin, A. M. Z. & Woollins, J. D. (2005). Dalton Trans. pp. 2188–2194.  Web of Science CSD CrossRef Google Scholar
First citationHua, G., Li, Y., Slawin, A. M. Z. & Woollins, J. D. (2006). Org. Lett. 8, 5251–5254.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationHua, G. & Woollins, J. D. (2007). Tetrahedron Lett. 48, 3677–3679.  Web of Science CrossRef CAS Google Scholar
First citationMugesh, G., Du Mont, W.-W. & Sies, H. (2001). Chem. Rev. 101, 2125–2179.  Web of Science CrossRef PubMed CAS Google Scholar
First citationRigaku (2004). CrystalClear. Version 1.36. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2003). SHELXTL. Version 6.14. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationShi, W., Shafaei-Fallah, M., Anson, C. E. & Rothenberger, A. (2006). Dalton Trans. pp. 2979–2983.  Web of Science CSD CrossRef Google Scholar
First citationShi, W., Shafaei-Fallah, M., Zhang, L., Anson, C. E., Matern, E. & Rothenberger, A. (2007). Chem. Eur. J. 13, 598–603.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSommen, G. L., Linden, A. & Heimgartner, H. (2005). Helv. Chim. Acta, 88, 766–773.  Web of Science CSD CrossRef CAS Google Scholar
First citationYoshifuji, M., An, D. L., Higeta, N. & Toyota, K. (1998). Chem. Lett. pp. 17–18.  CSD CrossRef Google Scholar

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