5-Benzyl-idene-2,3-diphenyl-1,2-selenaphosphole-2-selenide.

The title compound, C(23)H(19)PSe(2), has a central five-membered twist C(3)PSe ring conformation. One phenyl ring substituent, attached to an sp(2) carbon, is approximately coplanar with the C(3)PSe 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 = 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

Δρmax = 0.95 e Å−3

Δρmin = −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.

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

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

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

C23H19PSe2	F000 = 1920
Mr = 484.27	Dx = 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

Rigaku Mercury CCD diffractometer	3667 independent reflections
Radiation source: rotating anode	3125 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.043
T = 93(2) K	θmax = 25.5º
ω and φ scans	θmin = 2.3º
Absorption correction: multi-scan(CrystalClear; Rigaku,2004)	h = −26→17
Tmin = 0.515, Tmax = 0.692	k = −18→18
11508 measured reflections	l = −15→15

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(Fo2) + (0.032P)2 + 14.4806P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3667 reflections	Δρmax = 0.95 e Å−3
235 parameters	Δρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)