1,5,6-Triphenyl-8-oxa-7-selena-6-phos­phabicyclo­[3.2.1]octane-6-selone

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

doi:10.1107/S1600536807063945

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o184

https://doi.org/10.1107/S1600536807063945

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1,5,6-Triphenyl-8-oxa-7-selena-6-phosphabicyclo[3.2.1]octane-6-selone

Guoxiong Hua,^a Yang Li,^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 18 November 2007; accepted 27 November 2007; online 6 December 2007)

The structure of the title compound, C₂₃H₂₁OPSe₂, consists of fused puckered five- and six-membered rings, PSeC₂O and C₅O, respectively, with a C₂O bridgehead. The C₅O ring adopts a chair conformation, whilst the C₂PSeO ring has an envelope conformation.

Related literature

For related literature, see: An et al. (1998 ); Bhattacharyya et al. (2000 , 2001a ,b , 2002 ); Fitzmaurice et al. (1988 ); Gray, Bhattacharyya et al. (2005 ), Gray, Slawin et al. (2005 ); Hua & Woollins (2007 ); Hua, Li et al. (2006 , 2007a ,b ,c ); Shi et al. (2006 , 2007 ).

Experimental

Crystal data

C₂₃H₂₁OPSe₂
M_r = 502.29
Triclinic, $[P \overline 1]$
a = 7.6802 (9) Å
b = 9.0613 (12) Å
c = 14.9070 (16) Å
α = 84.949 (8)°
β = 75.677 (7)°
γ = 89.266 (8)°
V = 1001.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 3.78 mm⁻¹
T = 93 (2) K
0.20 × 0.20 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004 ) T_min = 0.489, T_max = 0.570
7092 measured reflections
3805 independent reflections
3000 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.072
S = 1.00
3805 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.82 e Å⁻³

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: SHELXTL (Sheldrick,2003 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807063945/pv2051sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063945/pv2051Isup2.hkl

checkCIF report

Comment top

2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (PhPSe₂)₂, also known as Woollins reagent, WR, is a selenium analogue of the well known Lawessons reagent, (p-MeOPhPS₂)₂. WR has found applications in the synthesis of selenium containing organic molecules, P—Se containing heterocycles and related compounds (Gray, Bhattacharyya et al.., 2005; Gray, Slawin et al.., 2005, Shi et al., 2006, 2007, Bhattacharyya et al. 2000, 2001a, 2001b, 2002, Hua, Li et al. 2006, 2007a, 2007b, 2007c). We report here the synthesis and X-ray structure of a new fused [3,2,1] ring P—Se heterocycle. The title compound, (I), was generated by the reaction of Woollins' reagent with 1,4-diketone. The P = Se bond length (2.0995 (9) Å) and the P – Se distance (2.2278 (10) Å) are consistent with the related selenides-containing P^V= Se bonds (2.08 – 2.12 Å) and P^V—Se single bonds (Fitzmaurice et al. 1988, An et al. 1998).

Related literature top

For related literature, see: An et al. (1998); Bhattacharyya et al. (2000, 2001a,b, 2002); Fitzmaurice et al. (1988); Gray, Bhattacharyya et al. (2005), Gray, Slawin et al. (2005); Hua & Woollins (2007); Hua, Li et al. (2006, 2007a,b,c); Shi et al. (2006, 2007).

Experimental top

A red suspension of 1,3-dibenzoylpropane (0.25 g, 1 mmol) and Woollins' reagent (0.54 g, 1 mmol) in dry toluene (10 ml) was refluxed for 16 hr. The yellow suspension was formed along with small amount of grey elemental selenium. Upon cooling to room temperature the mixture was purified by silica gel chromatography (1:9 ethyl acetate/dichloromethane as eluent) to give the title compound in 20% yield. Crystals were obtained from dichloromethane/hexane by diffusion method.

Structure description top

For related literature, see: An et al. (1998); Bhattacharyya et al. (2000, 2001a,b, 2002); Fitzmaurice et al. (1988); Gray, Bhattacharyya et al. (2005), Gray, Slawin et al. (2005); Hua & Woollins (2007); Hua, Li et al. (2006, 2007a,b,c); Shi et al. (2006, 2007).

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: SHELXTL (Sheldrick,2003); software used to prepare material for publication: SHELXTL (Sheldrick,2003).

Figures top

Fig. 1. The structure of (I) with displacement ellipsoids drawn at the 50% probability level; H-atoms have been ignored for clarity.

1,5,6-Triphenyl-8-oxa-7-selena-6-phosphabicyclo[3.2.1]octane-6-selone top

Crystal data top

C₂₃H₂₁OPSe₂	Z = 2
M_r = 502.29	F(000) = 500
Triclinic, P1	D_x = 1.666 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6802 (9) Å	Cell parameters from 3344 reflections
b = 9.0613 (12) Å	θ = 2.3–28.4°
c = 14.9070 (16) Å	µ = 3.78 mm⁻¹
α = 84.949 (8)°	T = 93 K
β = 75.677 (7)°	Block, colorless
γ = 89.266 (8)°	0.20 × 0.20 × 0.15 mm
V = 1001.2 (2) Å³

Data collection top

Rigaku Mercury CCD diffractometer	3805 independent reflections
Radiation source: rotating anode	3000 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.031
ω and φ scans	θ_max = 25.8°, θ_min = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004)	h = −10→9
T_min = 0.489, T_max = 0.570	k = −10→10
7092 measured reflections	l = −15→19

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0278P)²] where P = (F_o² + 2F_c²)/3
3805 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.82 e Å⁻³

Crystal data top

C₂₃H₂₁OPSe₂	γ = 89.266 (8)°
M_r = 502.29	V = 1001.2 (2) Å³
Triclinic, P1	Z = 2
a = 7.6802 (9) Å	Mo Kα radiation
b = 9.0613 (12) Å	µ = 3.78 mm⁻¹
c = 14.9070 (16) Å	T = 93 K
α = 84.949 (8)°	0.20 × 0.20 × 0.15 mm
β = 75.677 (7)°

Data collection top

Rigaku Mercury CCD diffractometer	3805 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004)	3000 reflections with I > 2σ(I)
T_min = 0.489, T_max = 0.570	R_int = 0.031
7092 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.00	Δρ_max = 0.85 e Å⁻³
3805 reflections	Δρ_min = −0.82 e Å⁻³
244 parameters

Special details top

Experimental. Anal. Calcd for C₂₃H₂₁OPSe₂: C, 55.00; H, 4.21. Found: C, 54.86; H, 4.15. ¹H NMR (CDCl₃): 7.72–7.05 (m, 15H, ArH), 2.37 (m, 4H, CH₂), 1.25 (m, 2H, CH₂). ³¹P NMR (CDCl₃): 79.23 (s, J(P,Se_endo) = 430 Hz, J(P,Se_exo) = 776 Hz). ⁷⁷Se NMR (CDCl₃): 34.61 (d, J(P,Se_endo) = 430 Hz), -94.02 (d, J(P,Se_exo) = 778 Hz).

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
C2	0.3921 (4)	0.3495 (4)	0.1438 (2)	0.0194 (8)
H2	0.3059	0.4106	0.1799	0.023*
Se2	0.56063 (4)	0.04366 (4)	0.35534 (2)	0.01561 (11)
Se1	0.26388 (4)	0.37283 (4)	0.37994 (2)	0.01944 (11)
P1	0.49881 (10)	0.27352 (10)	0.30698 (6)	0.0137 (2)
O1	0.8475 (3)	0.2463 (2)	0.29505 (14)	0.0147 (5)
C10	0.8065 (4)	0.1527 (4)	0.4568 (2)	0.0163 (8)
H10A	0.9283	0.1826	0.4598	0.020*
H10B	0.7710	0.0625	0.4999	0.020*
C18	0.9461 (4)	0.0000 (4)	0.3233 (2)	0.0161 (8)
C1	0.5138 (4)	0.2689 (4)	0.1839 (2)	0.0151 (7)
C12	0.7708 (4)	0.4895 (4)	0.2422 (2)	0.0133 (7)
C11	0.8112 (4)	0.1176 (4)	0.3592 (2)	0.0159 (8)
C8	0.7048 (4)	0.4071 (4)	0.4139 (2)	0.0167 (8)
H8A	0.6044	0.4773	0.4299	0.020*
H8B	0.8170	0.4596	0.4140	0.020*
C6	0.6430 (4)	0.1821 (4)	0.1293 (2)	0.0176 (8)
H6	0.7276	0.1285	0.1560	0.021*
C17	0.6750 (4)	0.6216 (4)	0.2523 (2)	0.0180 (8)
H17	0.5753	0.6289	0.3041	0.022*
C4	0.5238 (5)	0.2527 (4)	−0.0025 (2)	0.0275 (9)
H4	0.5262	0.2462	−0.0660	0.033*
C5	0.6475 (4)	0.1744 (4)	0.0366 (2)	0.0229 (9)
H5	0.7353	0.1155	−0.0004	0.027*
C21	1.1979 (4)	−0.2146 (4)	0.2626 (2)	0.0217 (9)
H21	1.2835	−0.2883	0.2412	0.026*
C9	0.6751 (4)	0.2765 (4)	0.4882 (2)	0.0165 (8)
H9A	0.6923	0.3096	0.5470	0.020*
H9B	0.5503	0.2389	0.4998	0.020*
C16	0.7245 (4)	0.7418 (4)	0.1872 (2)	0.0207 (8)
H16	0.6582	0.8310	0.1942	0.025*
C22	1.0516 (4)	−0.2490 (4)	0.3370 (2)	0.0228 (9)
H22	1.0371	−0.3465	0.3672	0.027*
C14	0.9652 (4)	0.6018 (4)	0.1018 (2)	0.0217 (8)
H14	1.0655	0.5954	0.0501	0.026*
C19	1.0923 (4)	0.0345 (4)	0.2492 (2)	0.0203 (8)
H19	1.1063	0.1316	0.2184	0.024*
C3	0.3977 (4)	0.3398 (4)	0.0505 (2)	0.0263 (9)
H3	0.3141	0.3936	0.0232	0.032*
C23	0.9267 (4)	−0.1415 (4)	0.3674 (2)	0.0212 (8)
H23	0.8271	−0.1652	0.4187	0.025*
C7	0.7176 (4)	0.3607 (4)	0.3169 (2)	0.0134 (7)
C13	0.9160 (4)	0.4807 (4)	0.1661 (2)	0.0182 (8)
H13	0.9817	0.3913	0.1582	0.022*
C15	0.8693 (4)	0.7326 (4)	0.1122 (2)	0.0231 (9)
H15	0.9035	0.8154	0.0678	0.028*
C20	1.2179 (4)	−0.0732 (4)	0.2201 (2)	0.0222 (9)
H20	1.3195	−0.0488	0.1700	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0152 (17)	0.022 (2)	0.0206 (19)	0.0026 (15)	−0.0049 (15)	0.0004 (15)
Se2	0.01333 (18)	0.0149 (2)	0.0184 (2)	−0.00064 (13)	−0.00467 (15)	0.00179 (14)
Se1	0.01320 (18)	0.0222 (2)	0.0215 (2)	0.00329 (14)	−0.00123 (15)	−0.00340 (15)
P1	0.0122 (4)	0.0142 (5)	0.0143 (4)	0.0011 (3)	−0.0029 (4)	−0.0009 (4)
O1	0.0150 (11)	0.0130 (14)	0.0160 (12)	0.0019 (9)	−0.0046 (10)	0.0014 (10)
C10	0.0132 (16)	0.022 (2)	0.0150 (17)	−0.0037 (14)	−0.0056 (14)	0.0009 (14)
C18	0.0137 (17)	0.017 (2)	0.0194 (18)	0.0013 (14)	−0.0081 (16)	−0.0017 (15)
C1	0.0130 (16)	0.015 (2)	0.0170 (18)	−0.0060 (14)	−0.0038 (15)	0.0000 (14)
C12	0.0148 (17)	0.013 (2)	0.0144 (17)	−0.0021 (13)	−0.0074 (15)	0.0001 (14)
C11	0.0109 (16)	0.015 (2)	0.0220 (19)	0.0024 (14)	−0.0047 (15)	−0.0018 (15)
C8	0.0149 (16)	0.021 (2)	0.0146 (17)	−0.0017 (14)	−0.0035 (15)	−0.0047 (15)
C6	0.0141 (17)	0.022 (2)	0.0169 (18)	0.0010 (15)	−0.0032 (15)	−0.0030 (15)
C17	0.0168 (17)	0.020 (2)	0.0191 (18)	0.0008 (15)	−0.0074 (15)	−0.0034 (15)
C4	0.029 (2)	0.041 (3)	0.0137 (19)	−0.0014 (18)	−0.0080 (17)	−0.0025 (17)
C5	0.0192 (18)	0.028 (2)	0.0196 (19)	0.0014 (16)	−0.0011 (16)	−0.0051 (16)
C21	0.0178 (18)	0.023 (2)	0.027 (2)	0.0077 (15)	−0.0098 (17)	−0.0090 (16)
C9	0.0174 (17)	0.019 (2)	0.0137 (17)	0.0009 (14)	−0.0047 (15)	−0.0009 (14)
C16	0.0237 (19)	0.014 (2)	0.025 (2)	0.0037 (15)	−0.0079 (17)	−0.0016 (15)
C22	0.026 (2)	0.016 (2)	0.030 (2)	0.0033 (15)	−0.0160 (18)	0.0037 (16)
C14	0.0199 (18)	0.025 (2)	0.0171 (18)	0.0008 (16)	−0.0005 (16)	0.0013 (15)
C19	0.0184 (18)	0.016 (2)	0.025 (2)	0.0001 (15)	−0.0035 (16)	0.0009 (15)
C3	0.027 (2)	0.032 (3)	0.023 (2)	0.0042 (17)	−0.0144 (18)	0.0028 (17)
C23	0.0163 (17)	0.025 (2)	0.0233 (19)	0.0024 (15)	−0.0087 (16)	0.0031 (16)
C7	0.0094 (15)	0.012 (2)	0.0198 (18)	0.0029 (13)	−0.0047 (14)	−0.0054 (14)
C13	0.0149 (17)	0.019 (2)	0.0201 (18)	0.0013 (15)	−0.0033 (16)	−0.0024 (15)
C15	0.026 (2)	0.021 (2)	0.0215 (19)	−0.0041 (16)	−0.0064 (17)	0.0048 (16)
C20	0.0136 (17)	0.022 (2)	0.028 (2)	0.0002 (15)	0.0006 (16)	−0.0033 (16)

Geometric parameters (Å, º) top

C2—C3	1.391 (5)	C6—H6	0.9500
C2—C1	1.395 (4)	C17—C16	1.384 (5)
C2—H2	0.9500	C17—H17	0.9500
Se2—C11	2.062 (3)	C4—C3	1.377 (5)
Se2—P1	2.2278 (10)	C4—C5	1.389 (5)
Se1—P1	2.0995 (9)	C4—H4	0.9500
P1—C1	1.814 (3)	C5—H5	0.9500
P1—C7	1.909 (3)	C21—C20	1.371 (5)
O1—C11	1.425 (4)	C21—C22	1.387 (5)
O1—C7	1.432 (3)	C21—H21	0.9500
C10—C11	1.509 (4)	C9—H9A	0.9900
C10—C9	1.525 (4)	C9—H9B	0.9900
C10—H10A	0.9900	C16—C15	1.375 (4)
C10—H10B	0.9900	C16—H16	0.9500
C18—C23	1.381 (5)	C22—C23	1.383 (5)
C18—C19	1.384 (4)	C22—H22	0.9500
C18—C11	1.514 (4)	C14—C13	1.383 (4)
C1—C6	1.400 (4)	C14—C15	1.387 (5)
C12—C13	1.387 (4)	C14—H14	0.9500
C12—C17	1.396 (4)	C19—C20	1.383 (4)
C12—C7	1.525 (4)	C19—H19	0.9500
C8—C7	1.521 (4)	C3—H3	0.9500
C8—C9	1.526 (4)	C23—H23	0.9500
C8—H8A	0.9900	C13—H13	0.9500
C8—H8B	0.9900	C15—H15	0.9500
C6—C5	1.381 (4)	C20—H20	0.9500

C3—C2—C1	119.6 (3)	C5—C4—H4	119.9
C3—C2—H2	120.2	C6—C5—C4	120.1 (3)
C1—C2—H2	120.2	C6—C5—H5	120.0
C11—Se2—P1	88.68 (9)	C4—C5—H5	120.0
C1—P1—C7	106.71 (14)	C20—C21—C22	119.4 (3)
C1—P1—Se1	113.82 (10)	C20—C21—H21	120.3
C7—P1—Se1	114.85 (10)	C22—C21—H21	120.3
C1—P1—Se2	105.00 (11)	C10—C9—C8	110.4 (3)
C7—P1—Se2	95.97 (10)	C10—C9—H9A	109.6
Se1—P1—Se2	118.47 (4)	C8—C9—H9A	109.6
C11—O1—C7	113.5 (2)	C10—C9—H9B	109.6
C11—C10—C9	111.9 (3)	C8—C9—H9B	109.6
C11—C10—H10A	109.2	H9A—C9—H9B	108.1
C9—C10—H10A	109.2	C15—C16—C17	120.3 (3)
C11—C10—H10B	109.2	C15—C16—H16	119.9
C9—C10—H10B	109.2	C17—C16—H16	119.9
H10A—C10—H10B	107.9	C23—C22—C21	120.0 (3)
C23—C18—C19	119.7 (3)	C23—C22—H22	120.0
C23—C18—C11	119.6 (3)	C21—C22—H22	120.0
C19—C18—C11	120.6 (3)	C13—C14—C15	120.4 (3)
C2—C1—C6	119.7 (3)	C13—C14—H14	119.8
C2—C1—P1	119.6 (2)	C15—C14—H14	119.8
C6—C1—P1	120.7 (2)	C20—C19—C18	119.6 (3)
C13—C12—C17	119.1 (3)	C20—C19—H19	120.2
C13—C12—C7	121.7 (3)	C18—C19—H19	120.2
C17—C12—C7	119.2 (3)	C4—C3—C2	120.4 (3)
O1—C11—C10	111.8 (3)	C4—C3—H3	119.8
O1—C11—C18	108.3 (2)	C2—C3—H3	119.8
C10—C11—C18	113.8 (3)	C18—C23—C22	120.3 (3)
O1—C11—Se2	105.63 (19)	C18—C23—H23	119.9
C10—C11—Se2	109.0 (2)	C22—C23—H23	119.9
C18—C11—Se2	107.8 (2)	O1—C7—C8	110.9 (3)
C7—C8—C9	113.0 (3)	O1—C7—C12	107.9 (2)
C7—C8—H8A	109.0	C8—C7—C12	112.2 (3)
C9—C8—H8A	109.0	O1—C7—P1	104.0 (2)
C7—C8—H8B	109.0	C8—C7—P1	112.1 (2)
C9—C8—H8B	109.0	C12—C7—P1	109.4 (2)
H8A—C8—H8B	107.8	C14—C13—C12	120.2 (3)
C5—C6—C1	120.0 (3)	C14—C13—H13	119.9
C5—C6—H6	120.0	C12—C13—H13	119.9
C1—C6—H6	120.0	C16—C15—C14	119.7 (3)
C16—C17—C12	120.3 (3)	C16—C15—H15	120.1
C16—C17—H17	119.8	C14—C15—H15	120.1
C12—C17—H17	119.8	C21—C20—C19	121.0 (3)
C3—C4—C5	120.3 (3)	C21—C20—H20	119.5
C3—C4—H4	119.9	C19—C20—H20	119.5

C11—Se2—P1—C1	104.65 (14)	C23—C18—C19—C20	−0.2 (5)
C11—Se2—P1—C7	−4.46 (13)	C11—C18—C19—C20	177.3 (3)
C11—Se2—P1—Se1	−126.97 (10)	C5—C4—C3—C2	−0.4 (6)
C3—C2—C1—C6	1.6 (5)	C1—C2—C3—C4	−0.8 (5)
C3—C2—C1—P1	−176.7 (3)	C19—C18—C23—C22	−0.7 (5)
C7—P1—C1—C2	−117.1 (3)	C11—C18—C23—C22	−178.2 (3)
Se1—P1—C1—C2	10.6 (3)	C21—C22—C23—C18	0.5 (5)
Se2—P1—C1—C2	141.8 (3)	C11—O1—C7—C8	57.7 (3)
C7—P1—C1—C6	64.7 (3)	C11—O1—C7—C12	−179.0 (3)
Se1—P1—C1—C6	−167.6 (2)	C11—O1—C7—P1	−63.0 (3)
Se2—P1—C1—C6	−36.4 (3)	C9—C8—C7—O1	−52.0 (3)
C7—O1—C11—C10	−59.4 (3)	C9—C8—C7—C12	−172.7 (2)
C7—O1—C11—C18	174.3 (3)	C9—C8—C7—P1	63.7 (3)
C7—O1—C11—Se2	59.0 (3)	C13—C12—C7—O1	3.9 (4)
C9—C10—C11—O1	54.2 (3)	C17—C12—C7—O1	−173.9 (3)
C9—C10—C11—C18	177.4 (3)	C13—C12—C7—C8	126.3 (3)
C9—C10—C11—Se2	−62.2 (3)	C17—C12—C7—C8	−51.5 (4)
C23—C18—C11—O1	−172.4 (3)	C13—C12—C7—P1	−108.6 (3)
C19—C18—C11—O1	10.1 (4)	C17—C12—C7—P1	73.6 (3)
C23—C18—C11—C10	62.5 (4)	C1—P1—C7—O1	−74.6 (2)
C19—C18—C11—C10	−115.0 (3)	Se1—P1—C7—O1	158.24 (15)
C23—C18—C11—Se2	−58.5 (4)	Se2—P1—C7—O1	33.03 (19)
C19—C18—C11—Se2	124.0 (3)	C1—P1—C7—C8	165.6 (2)
P1—Se2—C11—O1	−24.59 (19)	Se1—P1—C7—C8	38.4 (3)
P1—Se2—C11—C10	95.7 (2)	Se2—P1—C7—C8	−86.8 (2)
P1—Se2—C11—C18	−140.2 (2)	C1—P1—C7—C12	40.4 (3)
C2—C1—C6—C5	−1.2 (5)	Se1—P1—C7—C12	−86.7 (2)
P1—C1—C6—C5	177.0 (3)	Se2—P1—C7—C12	148.1 (2)
C13—C12—C17—C16	−0.1 (5)	C15—C14—C13—C12	−0.6 (5)
C7—C12—C17—C16	177.8 (3)	C17—C12—C13—C14	0.6 (5)
C1—C6—C5—C4	0.0 (5)	C7—C12—C13—C14	−177.2 (3)
C3—C4—C5—C6	0.8 (6)	C17—C16—C15—C14	0.4 (5)
C11—C10—C9—C8	−48.4 (4)	C13—C14—C15—C16	0.2 (6)
C7—C8—C9—C10	47.9 (4)	C22—C21—C20—C19	−1.4 (5)
C12—C17—C16—C15	−0.4 (5)	C18—C19—C20—C21	1.3 (6)
C20—C21—C22—C23	0.5 (5)

Experimental details

Crystal data
Chemical formula	C₂₃H₂₁OPSe₂
M_r	502.29
Crystal system, space group	Triclinic, P1
Temperature (K)	93
a, b, c (Å)	7.6802 (9), 9.0613 (12), 14.9070 (16)
α, β, γ (°)	84.949 (8), 75.677 (7), 89.266 (8)
V (Å³)	1001.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.78
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Rigaku Mercury CCD
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2004)
T_min, T_max	0.489, 0.570
No. of measured, independent and observed [I > 2σ(I)] reflections	7092, 3805, 3000
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.072, 1.00
No. of reflections	3805
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.82

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

Acknowledgements

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

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