1,5,6-Triphenyl-8-oxa-7-selena-6-phos-phabicyclo-[3.2.1]octane-6-selone.

The structure of the title compound, C(23)H(21)OPSe(2), consists of fused puckered five- and six-membered rings, PSeC(2)O and C(5)O, respectively, with a C(2)O bridgehead. The C(5)O ring adopts a chair conformation, whilst the C(2)PSeO 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 = 502.29

Triclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.072

S = 1.00

3805 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063945/pv2051Isup2.hkl

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

C23H21OPSe2	Z = 2
Mr = 502.29	F000 = 500
Triclinic, P1	Dx = 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 = 2.3–28.4º
c = 14.9070 (16) Å	µ = 3.78 mm−1
α = 84.949 (8)º	T = 93 (2) K
β = 75.677 (7)º	Block, colorless
γ = 89.266 (8)º	0.20 × 0.20 × 0.15 mm
V = 1001.2 (2) Å3

Rigaku Mercury CCD diffractometer	3805 independent reflections
Radiation source: rotating anode	3000 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.031
T = 93(2) K	θmax = 25.8º
ω and φ scans	θmin = 2.3º
Absorption correction: multi-scan(CrystalClear; Rigaku, 2004)	h = −10→9
Tmin = 0.489, Tmax = 0.570	k = −10→10
7092 measured reflections	l = −15→19

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.0278P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
3805 reflections	Δρmax = 0.85 e Å−3
244 parameters	Δρmin = −0.82 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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,Seendo) = 430 Hz, J(P,Seexo) = 776 Hz). 77Se NMR (CDCl3): 34.61 (d, J(P,Seendo) = 430 Hz), -94.02 (d, J(P,Seexo) = 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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)