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

Yang Li; Guoxiong Hua; Alexandra M Z Slawin; J Derek Woollins

doi:10.1107/S1600536807062228

. 2007 Dec 6;64(Pt 1):o4. doi: 10.1107/S1600536807062228

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

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

PMCID: PMC2914894 PMID: 21200914

Abstract

The title compound, C₂₃H₁₉PSe₂, has a central five-membered twist C₃PSe ring conformation. One phenyl ring substituent, attached to an sp ² carbon, is approximately coplanar with the C₃PSe ring whilst the other organic substituents, attached to an sp ³-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,
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[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 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

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.

Supplementary Material

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

e-64-000o4-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062228/si2054Isup2.hkl

e-64-000o4-Isup2.hkl^{(176.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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)

Open in a new tab

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)

Open in a new tab

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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).

Figures

Fig. 1. — The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Crystal data

C₂₃H₁₉PSe₂	F₀₀₀ = 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 = 1.6–25.3º
b = 14.4348 (14) Å	µ = 3.78 mm⁻¹
c = 12.4433 (12) Å	T = 93 (2) K
β = 94.847 (2)º	Prism, colorless
V = 4006.4 (7) Å³	0.30 × 0.15 × 0.10 mm
Z = 8

Open in a new tab

Data collection

Rigaku Mercury CCD diffractometer	3667 independent reflections
Radiation source: rotating anode	3125 reflections with I > 2σ(I)
Monochromator: confocal	R_int = 0.043
T = 93(2) K	θ_max = 25.5º
ω and φ scans	θ_min = 2.3º
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

Open in a new tab

Refinement

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.032P)² + 14.4806P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3667 reflections	Δρ_max = 0.95 e Å⁻³
235 parameters	Δρ_min = −0.41 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Open in a new tab

Special details

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.

Open in a new tab

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	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*

Open in a new tab

Atomic displacement parameters (Å²)

	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)

Open in a new tab

Geometric parameters (Å, °)

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)

Open in a new tab

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2054).

References

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

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-64-000o4-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062228/si2054Isup2.hkl

e-64-000o4-Isup2.hkl^{(176.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[bb1] Fitzmaurice, J. C., Williams, J. C., Wood, P. T. & Woollins, J. D. (1988). J. Chem. Soc. Chem. Commun. pp. 741–743.

[bb2] Gray, I. P., Bhattacharyya, P., Slawin, A. M. Z. & Woollins, J. D. (2005). Chem. Eur. J.11, 6221–6227. [DOI] [PubMed]

[bb3] Gray, I. P., Slawin, A. M. Z. & Woollins, J. D. (2005). Dalton Trans. pp. 2188–2194. [DOI] [PubMed]

[bb4] Hua, G., Li, Y., Slawin, A. M. Z. & Woollins, J. D. (2006). Org. Lett.8, 5251–5254. [DOI] [PubMed]

[bb5] Hua, G. & Woollins, J. D. (2007). Tetrahedron Lett.48, 3677–3679.

[bb6] Mugesh, G., Du Mont, W.-W. & Sies, H. (2001). Chem. Rev.101, 2125–2179. [DOI] [PubMed]

[bb7] Rigaku (2004). CrystalClear Version 1.36. Rigaku Corporation, Tokyo, Japan.

[bb8] Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.

[bb9] Sheldrick, G. M. (2003). SHELXTL Version 6.14. Bruker AXS Inc., Madison, Wisconsin, USA.

[bb10] Shi, W., Shafaei-Fallah, M., Anson, C. E. & Rothenberger, A. (2006). Dalton Trans. pp. 2979–2983. [DOI] [PubMed]

[bb11] Shi, W., Shafaei-Fallah, M., Zhang, L., Anson, C. E., Matern, E. & Rothenberger, A. (2007). Chem. Eur. J.13, 598–603. [DOI] [PubMed]

[bb12] Sommen, G. L., Linden, A. & Heimgartner, H. (2005). Helv. Chim. Acta, 88, 766–773.

[bb13] Yoshifuji, M., An, D. L., Higeta, N. & Toyota, K. (1998). Chem. Lett. pp. 17–18.

PERMALINK

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

Yang Li

Guoxiong Hua

Alexandra M Z Slawin

J Derek Woollins

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Table 1. Selected geometric parameters (Å, °).

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)

Geometric parameters (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

Cite

Add to Collections

PERMALINK

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

Yang Li

Guoxiong Hua

Alexandra M Z Slawin

J Derek Woollins

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Table 1. Selected geometric parameters (Å, °).

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

Atomic displacement parameters (Å2)

Geometric parameters (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

Similar articles

Cited by other articles

Links to NCBI Databases

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)