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

Li, Y.; Hua, G.; Slawin, A.M.Z.; Woollins, J.D.

doi:10.1107/S1600536807062228

organic compounds

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Volume 64| Part 1| January 2008| Page o4

https://doi.org/10.1107/S1600536807062228

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

Yang Li,^a Guoxiong Hua,^a Alexandra M. Z. Slawin ^a and J. Derek Woollins ^a ^*

^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 P^V atom, lie on the same side of the ring.

Related literature

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

Crystal data

C₂₃H₁₉PSe₂
M_r = 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 ) T_min = 0.515, T_max = 0.692
11508 measured reflections
3667 independent reflections
3125 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.077
S = 1.04
3667 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.95 e Å⁻³
Δρ_min = −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); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807062228/si2054sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062228/si2054Isup2.hkl

checkCIF report

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 P^V= Se bonds (2.081 (2) - 2.123 (3) Å) and P^V—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,Se_endo) = 350 Hz, J(P,Se_exo) = 782 Hz). ⁷⁷Se NMR (CDCl₃): 354.85 (J(P,Se_endo) = 350 Hz), -169.99 (J(P,Se_exo) = 780 Hz).

Structure description 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).

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

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

C₂₃H₁₉PSe₂	F(000) = 1920
M_r = 484.27	D_x = 1.606 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8628 reflections
a = 22.385 (2) Å	θ = 1.6–25.3°
b = 14.4348 (14) Å	µ = 3.78 mm⁻¹
c = 12.4433 (12) Å	T = 93 K
β = 94.847 (2)°	Prism, colorless
V = 4006.4 (7) Å³	0.30 × 0.15 × 0.10 mm
Z = 8

Data collection top

Rigaku Mercury CCD diffractometer	3667 independent reflections
Radiation source: rotating anode	3125 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.043
ω and φ scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku,2004)	h = −26→17
T_min = 0.515, T_max = 0.692	k = −18→18
11508 measured reflections	l = −15→15

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.077	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.032P)² + 14.4806P] where P = (F_o² + 2F_c²)/3
3667 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.95 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₃H₁₉PSe₂	V = 4006.4 (7) Å³
M_r = 484.27	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.385 (2) Å	µ = 3.78 mm⁻¹
b = 14.4348 (14) Å	T = 93 K
c = 12.4433 (12) Å	0.30 × 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)
T_min = 0.515, T_max = 0.692	R_int = 0.043
11508 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.032P)² + 14.4806P] where P = (F_o² + 2F_c²)/3
3667 reflections	Δρ_max = 0.95 e Å⁻³
235 parameters	Δρ_min = −0.41 e Å⁻³

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
Se2	0.946290 (15)	−0.03631 (2)	0.57968 (3)	0.02008 (10)
Se1	0.960236 (16)	0.21801 (2)	0.57205 (3)	0.02484 (11)
P1	0.90715 (4)	0.10413 (6)	0.60975 (7)	0.01702 (19)
C19	0.93533 (15)	−0.4014 (2)	0.5818 (3)	0.0236 (8)
H19	0.9426	−0.3743	0.5145	0.028*
C6	0.81730 (16)	0.1775 (2)	0.4664 (3)	0.0237 (8)
H6	0.8439	0.2281	0.4600	0.028*
C10	0.85050 (14)	0.1485 (2)	0.7960 (2)	0.0182 (7)
C2	0.79343 (16)	0.0315 (2)	0.5460 (3)	0.0254 (8)
H2	0.8042	−0.0188	0.5931	0.030*
C11	0.79206 (15)	0.1186 (3)	0.8016 (3)	0.0240 (8)
H11	0.7813	0.0573	0.7800	0.029*
C5	0.76207 (17)	0.1763 (3)	0.4063 (3)	0.0326 (9)
H5	0.7515	0.2253	0.3573	0.039*
C13	0.76399 (17)	0.2669 (3)	0.8696 (3)	0.0286 (9)
H13	0.7346	0.3072	0.8945	0.034*
C1	0.83355 (14)	0.1048 (2)	0.5360 (3)	0.0188 (7)
C15	0.86516 (16)	0.2385 (2)	0.8277 (3)	0.0245 (8)
H15	0.9050	0.2602	0.8245	0.029*
C22	0.91438 (18)	−0.4819 (3)	0.7761 (3)	0.0326 (9)
H22	0.9070	−0.5096	0.8430	0.039*
C18	0.92438 (14)	−0.3447 (2)	0.6681 (3)	0.0201 (7)
C3	0.73807 (17)	0.0323 (3)	0.4872 (3)	0.0330 (9)
H3	0.7106	−0.0169	0.4949	0.040*
C12	0.74889 (16)	0.1772 (3)	0.8384 (3)	0.0294 (8)
H12	0.7090	0.1556	0.8422	0.035*
C4	0.72257 (18)	0.1045 (3)	0.4173 (3)	0.0349 (9)
H4	0.6846	0.1046	0.3769	0.042*
C8	0.89178 (15)	−0.0157 (2)	0.7738 (2)	0.0202 (7)
H8	0.8729	−0.0357	0.8354	0.024*
C14	0.82195 (17)	0.2971 (3)	0.8641 (3)	0.0299 (9)
H14	0.8325	0.3586	0.8854	0.036*
C21	0.92538 (16)	−0.5374 (2)	0.6896 (3)	0.0294 (8)
H21	0.9258	−0.6029	0.6971	0.035*
C16	0.90956 (15)	−0.1790 (2)	0.7240 (3)	0.0216 (7)
H16	0.8966	−0.2003	0.7904	0.026*
C7	0.89842 (15)	0.0864 (2)	0.7559 (3)	0.0186 (7)
H7	0.9372	0.1052	0.7955	0.022*
C23	0.91395 (17)	−0.3864 (3)	0.7666 (3)	0.0274 (8)
H23	0.9066	−0.3490	0.8269	0.033*
C17	0.92483 (14)	−0.2435 (2)	0.6540 (3)	0.0196 (7)
H17	0.9374	−0.2214	0.5876	0.024*
C9	0.91106 (14)	−0.0799 (2)	0.7077 (3)	0.0185 (7)
C20	0.93580 (16)	−0.4975 (3)	0.5923 (3)	0.0292 (8)
H20	0.9433	−0.5354	0.5325	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se2	0.02552 (19)	0.01480 (18)	0.02139 (18)	0.00227 (13)	0.01059 (13)	0.00242 (14)
Se1	0.0290 (2)	0.01641 (18)	0.0306 (2)	−0.00455 (14)	0.01166 (15)	0.00100 (15)
P1	0.0214 (4)	0.0136 (4)	0.0169 (4)	−0.0008 (3)	0.0065 (3)	0.0003 (3)
C19	0.0256 (19)	0.0207 (18)	0.0248 (19)	−0.0015 (14)	0.0034 (14)	−0.0006 (15)
C6	0.0312 (19)	0.0211 (18)	0.0200 (18)	0.0048 (15)	0.0083 (14)	0.0030 (15)
C10	0.0246 (18)	0.0223 (18)	0.0078 (15)	0.0015 (14)	0.0013 (12)	0.0015 (14)
C2	0.032 (2)	0.0220 (18)	0.0214 (18)	−0.0023 (15)	−0.0003 (14)	0.0039 (16)
C11	0.0277 (19)	0.0263 (19)	0.0190 (18)	−0.0022 (15)	0.0076 (14)	−0.0020 (15)
C5	0.041 (2)	0.036 (2)	0.0207 (19)	0.0131 (18)	−0.0013 (16)	0.0044 (17)
C13	0.036 (2)	0.032 (2)	0.0183 (18)	0.0138 (17)	0.0096 (15)	0.0010 (16)
C1	0.0226 (17)	0.0199 (17)	0.0142 (16)	0.0005 (14)	0.0039 (13)	−0.0046 (14)
C15	0.0289 (19)	0.0238 (19)	0.0208 (18)	0.0001 (15)	0.0018 (14)	−0.0012 (15)
C22	0.048 (2)	0.023 (2)	0.026 (2)	−0.0017 (17)	−0.0025 (17)	0.0092 (17)
C18	0.0152 (16)	0.0176 (17)	0.0272 (19)	−0.0003 (13)	−0.0010 (13)	0.0009 (15)
C3	0.032 (2)	0.039 (2)	0.028 (2)	−0.0071 (18)	−0.0020 (16)	−0.0057 (19)
C12	0.0220 (18)	0.042 (2)	0.0252 (19)	−0.0006 (16)	0.0071 (14)	0.0067 (17)
C4	0.034 (2)	0.046 (3)	0.023 (2)	0.0075 (19)	−0.0058 (16)	−0.0061 (19)
C8	0.0263 (18)	0.0233 (19)	0.0114 (16)	0.0011 (14)	0.0036 (13)	0.0018 (14)
C14	0.042 (2)	0.022 (2)	0.026 (2)	0.0046 (16)	0.0036 (16)	−0.0053 (17)
C21	0.031 (2)	0.0151 (18)	0.040 (2)	−0.0019 (15)	−0.0068 (16)	0.0023 (17)
C16	0.0279 (19)	0.0191 (17)	0.0183 (17)	0.0011 (14)	0.0035 (14)	0.0067 (14)
C7	0.0214 (17)	0.0181 (17)	0.0164 (17)	−0.0001 (13)	0.0029 (13)	0.0022 (14)
C23	0.038 (2)	0.0219 (19)	0.0219 (19)	−0.0003 (16)	−0.0006 (15)	0.0008 (16)
C17	0.0195 (17)	0.0192 (17)	0.0204 (17)	−0.0013 (13)	0.0031 (13)	0.0034 (14)
C9	0.0205 (17)	0.0190 (17)	0.0159 (17)	0.0007 (13)	0.0013 (13)	0.0029 (14)
C20	0.031 (2)	0.0215 (19)	0.036 (2)	−0.0027 (15)	0.0029 (16)	−0.0058 (17)

Geometric parameters (Å, º) top

Se2—C9	1.941 (3)	C15—C14	1.389 (5)
Se2—P1	2.2523 (9)	C15—H15	0.9500
Se1—P1	2.1044 (9)	C22—C21	1.381 (5)
P1—C1	1.817 (3)	C22—C23	1.383 (5)
P1—C7	1.862 (3)	C22—H22	0.9500
C19—C18	1.389 (5)	C18—C23	1.402 (5)
C19—C20	1.393 (5)	C18—C17	1.472 (5)
C19—H19	0.9500	C3—C4	1.383 (6)
C6—C5	1.390 (5)	C3—H3	0.9500
C6—C1	1.390 (5)	C12—H12	0.9500
C6—H6	0.9500	C4—H4	0.9500
C10—C11	1.385 (5)	C8—C9	1.334 (5)
C10—C15	1.389 (5)	C8—C7	1.500 (5)
C10—C7	1.515 (4)	C8—H8	0.9500
C2—C3	1.385 (5)	C14—H14	0.9500
C2—C1	1.400 (5)	C21—C20	1.378 (5)
C2—H2	0.9500	C21—H21	0.9500
C11—C12	1.390 (5)	C16—C17	1.339 (5)
C11—H11	0.9500	C16—C9	1.446 (5)
C5—C4	1.377 (6)	C16—H16	0.9500
C5—H5	0.9500	C7—H7	1.0000
C13—C14	1.376 (5)	C23—H23	0.9500
C13—C12	1.385 (5)	C17—H17	0.9500
C13—H13	0.9500	C20—H20	0.9500

C9—Se2—P1	87.97 (10)	C4—C3—C2	120.3 (4)
C1—P1—C7	109.16 (15)	C4—C3—H3	119.8
C1—P1—Se1	112.86 (11)	C2—C3—H3	119.8
C7—P1—Se1	115.65 (11)	C13—C12—C11	120.0 (3)
C1—P1—Se2	105.64 (11)	C13—C12—H12	120.0
C7—P1—Se2	96.47 (10)	C11—C12—H12	120.0
Se1—P1—Se2	115.54 (4)	C5—C4—C3	120.1 (4)
C18—C19—C20	120.9 (3)	C5—C4—H4	120.0
C18—C19—H19	119.5	C3—C4—H4	120.0
C20—C19—H19	119.5	C9—C8—C7	123.3 (3)
C5—C6—C1	120.0 (3)	C9—C8—H8	118.4
C5—C6—H6	120.0	C7—C8—H8	118.4
C1—C6—H6	120.0	C13—C14—C15	120.6 (3)
C11—C10—C15	118.6 (3)	C13—C14—H14	119.7
C11—C10—C7	122.0 (3)	C15—C14—H14	119.7
C15—C10—C7	119.4 (3)	C20—C21—C22	119.7 (3)
C3—C2—C1	119.9 (3)	C20—C21—H21	120.1
C3—C2—H2	120.1	C22—C21—H21	120.1
C1—C2—H2	120.1	C17—C16—C9	125.9 (3)
C10—C11—C12	120.9 (3)	C17—C16—H16	117.1
C10—C11—H11	119.6	C9—C16—H16	117.1
C12—C11—H11	119.6	C8—C7—C10	116.8 (3)
C4—C5—C6	120.3 (4)	C8—C7—P1	107.5 (2)
C4—C5—H5	119.8	C10—C7—P1	112.1 (2)
C6—C5—H5	119.8	C8—C7—H7	106.6
C14—C13—C12	119.4 (3)	C10—C7—H7	106.6
C14—C13—H13	120.3	P1—C7—H7	106.6
C12—C13—H13	120.3	C22—C23—C18	120.2 (3)
C6—C1—C2	119.4 (3)	C22—C23—H23	119.9
C6—C1—P1	119.8 (3)	C18—C23—H23	119.9
C2—C1—P1	120.8 (3)	C16—C17—C18	127.4 (3)
C14—C15—C10	120.5 (3)	C16—C17—H17	116.3
C14—C15—H15	119.7	C18—C17—H17	116.3
C10—C15—H15	119.7	C8—C9—C16	126.0 (3)
C21—C22—C23	120.8 (3)	C8—C9—Se2	117.1 (2)
C21—C22—H22	119.6	C16—C9—Se2	116.8 (2)
C23—C22—H22	119.6	C21—C20—C19	119.9 (3)
C19—C18—C23	118.4 (3)	C21—C20—H20	120.0
C19—C18—C17	119.3 (3)	C19—C20—H20	120.0
C23—C18—C17	122.3 (3)

C9—Se2—P1—C1	−90.70 (14)	C23—C22—C21—C20	−0.3 (6)
C9—Se2—P1—C7	21.31 (14)	C9—C8—C7—C10	149.3 (3)
C9—Se2—P1—Se1	143.79 (10)	C9—C8—C7—P1	22.4 (4)
C15—C10—C11—C12	−0.2 (5)	C11—C10—C7—C8	−29.5 (4)
C7—C10—C11—C12	−179.8 (3)	C15—C10—C7—C8	150.9 (3)
C1—C6—C5—C4	1.7 (5)	C11—C10—C7—P1	95.1 (3)
C5—C6—C1—C2	−1.0 (5)	C15—C10—C7—P1	−84.5 (3)
C5—C6—C1—P1	177.2 (3)	C1—P1—C7—C8	82.6 (2)
C3—C2—C1—C6	−0.3 (5)	Se1—P1—C7—C8	−148.82 (19)
C3—C2—C1—P1	−178.5 (3)	Se2—P1—C7—C8	−26.4 (2)
C7—P1—C1—C6	128.1 (3)	C1—P1—C7—C10	−47.0 (3)
Se1—P1—C1—C6	−2.0 (3)	Se1—P1—C7—C10	81.5 (2)
Se2—P1—C1—C6	−129.2 (2)	Se2—P1—C7—C10	−156.1 (2)
C7—P1—C1—C2	−53.7 (3)	C21—C22—C23—C18	0.4 (6)
Se1—P1—C1—C2	176.2 (2)	C19—C18—C23—C22	−0.3 (5)
Se2—P1—C1—C2	49.1 (3)	C17—C18—C23—C22	−179.6 (3)
C11—C10—C15—C14	−0.1 (5)	C9—C16—C17—C18	179.4 (3)
C7—C10—C15—C14	179.6 (3)	C19—C18—C17—C16	172.9 (3)
C20—C19—C18—C23	0.2 (5)	C23—C18—C17—C16	−7.9 (5)
C20—C19—C18—C17	179.4 (3)	C7—C8—C9—C16	175.7 (3)
C1—C2—C3—C4	1.0 (5)	C7—C8—C9—Se2	−2.5 (4)
C14—C13—C12—C11	−0.3 (5)	C17—C16—C9—C8	174.8 (3)
C10—C11—C12—C13	0.3 (5)	C17—C16—C9—Se2	−6.9 (5)
C6—C5—C4—C3	−1.0 (6)	P1—Se2—C9—C8	−14.4 (3)
C2—C3—C4—C5	−0.4 (6)	P1—Se2—C9—C16	167.2 (3)
C12—C13—C14—C15	0.0 (5)	C22—C21—C20—C19	0.2 (5)
C10—C15—C14—C13	0.2 (5)	C18—C19—C20—C21	−0.1 (5)

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉PSe₂
M_r	484.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	93
a, b, c (Å)	22.385 (2), 14.4348 (14), 12.4433 (12)
β (°)	94.847 (2)
V (Å³)	4006.4 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.78
Crystal size (mm)	0.30 × 0.15 × 0.10

Data collection
Diffractometer	Rigaku Mercury CCD
Absorption correction	Multi-scan (CrystalClear; Rigaku,2004)
T_min, T_max	0.515, 0.692
No. of measured, independent and observed [I > 2σ(I)] reflections	11508, 3667, 3125
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.607

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.077, 1.04
No. of reflections	3667
No. of parameters	235
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.032P)² + 14.4806P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	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—C9	1.941 (3)	P1—C7	1.862 (3)
Se2—P1	2.2523 (9)	C8—C9	1.334 (5)
Se1—P1	2.1044 (9)	C8—C7	1.500 (5)
P1—C1	1.817 (3)

C9—Se2—P1	87.97 (10)	C7—P1—Se2	96.47 (10)
C1—P1—C7	109.16 (15)	Se1—P1—Se2	115.54 (4)
C1—P1—Se1	112.86 (11)	C9—C8—C7	123.3 (3)
C7—P1—Se1	115.65 (11)	C8—C7—P1	107.5 (2)
C1—P1—Se2	105.64 (11)	C8—C9—Se2	117.1 (2)

Acknowledgements

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

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