Literature DB >> 22969582

(4-Ethenylphen-yl)diphenyl-phosphine selenide.

Zanele H Phasha¹, Sizwe Makhoba, Alfred Muller.

Abstract

In the title mol-ecule, C(10)H(17)PSe, the P atom has a distorted tetra-hedral environment resulting in an effective cone angle of 165°. The benzene ring makes dihedral angles of 70.04 (8) and 77.28 (8)° with the phenyl rings, while the dihedral angle between the phenyl rings is 62.95 (8)°. In the crystal, mol-ecules are linked by C-H⋯π inter-actions.

Entities: Chemical Disease Gene Species

Year: 2012 PMID： 22969582 PMCID： PMC3435711 DOI： 10.1107/S1600536812034289

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to our investigation of the steric and electronic effects of group 15 ligands, see: Roodt et al. (2003 ▶); Muller et al. (2006 ▶, 2008 ▶). For background to cone angles, see: Bunten et al. (2002 ▶); Tolman (1977 ▶); Otto (2001 ▶).

Experimental

Crystal data

C20H17PSe M = 367.27 Monoclinic, a = 10.5310 (7) Å b = 11.1477 (7) Å c = 17.2187 (9) Å β = 124.562 (3)° V = 1664.66 (18) Å3 Z = 4 Mo Kα radiation μ = 2.35 mm−1 T = 100 K 0.3 × 0.25 × 0.13 mm

Data collection

Bruker APEX DUO 4K-CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.526, T max = 0.737 20089 measured reflections 4166 independent reflections 3921 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.024 wR(F 2) = 0.063 S = 1.03 4166 reflections 199 parameters H-atom parameters constrained Δρmax = 1.37 e Å−3 Δρmin = −0.41 e Å−3 Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034289/is5175sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034289/is5175Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812034289/is5175Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₀H₁₇PSe	F(000) = 744
M_r = 367.27	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9906 reflections
a = 10.5310 (7) Å	θ = 2.5–28.4°
b = 11.1477 (7) Å	µ = 2.35 mm⁻¹
c = 17.2187 (9) Å	T = 100 K
β = 124.562 (3)°	Plate, colourless
V = 1664.66 (18) Å³	0.3 × 0.25 × 0.13 mm
Z = 4

Bruker APEX DUO 4K-CCD diffractometer	4166 independent reflections
Graphite monochromator	3921 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm^-1	R_int = 0.028
φ and ω scans	θ_max = 28.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
T_min = 0.526, T_max = 0.737	k = −14→14
20089 measured reflections	l = −16→22

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.032P)² + 1.0912P] where P = (F_o² + 2F_c²)/3
4166 reflections	(Δ/σ)_max = 0.002
199 parameters	Δρ_max = 1.37 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 1.5 s/frame. A total of 1478 frames were collected with a frame width of 0.5° covering up to θ = 28.40° with 99.9% completeness accomplished.

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	U_iso*/U_eq
C1	0.32208 (15)	0.17035 (12)	0.77818 (9)	0.0137 (2)
C2	0.42929 (16)	0.09481 (13)	0.85112 (10)	0.0168 (3)
H2	0.534	0.119	0.8916	0.02*
C3	0.38312 (16)	−0.01578 (13)	0.86458 (10)	0.0179 (3)
H3	0.4572	−0.0668	0.9139	0.021*
C4	0.22952 (17)	−0.05274 (12)	0.80657 (10)	0.0165 (3)
C5	0.12331 (16)	0.02363 (13)	0.73350 (10)	0.0178 (3)
H5	0.0186	−0.0005	0.693	0.021*
C6	0.16804 (16)	0.13364 (13)	0.71908 (10)	0.0165 (3)
H6	0.0942	0.1841	0.6691	0.02*
C7	0.17416 (18)	−0.16732 (13)	0.81962 (11)	0.0222 (3)
H7	0.0663	−0.1817	0.7798	0.027*
C8	0.2598 (2)	−0.25211 (14)	0.88126 (13)	0.0269 (3)
H8A	0.3683	−0.242	0.9226	0.032*
H8B	0.2129	−0.3232	0.8842	0.032*
C9	0.58097 (15)	0.32505 (12)	0.83389 (9)	0.0151 (2)
C10	0.66759 (16)	0.24875 (14)	0.81638 (10)	0.0198 (3)
H10	0.6167	0.1951	0.7644	0.024*
C11	0.82745 (17)	0.25109 (14)	0.87468 (11)	0.0226 (3)
H11	0.8857	0.1982	0.8631	0.027*
C12	0.90255 (17)	0.33079 (15)	0.95012 (11)	0.0242 (3)
H12	1.012	0.3324	0.99	0.029*
C13	0.81748 (18)	0.40761 (15)	0.96690 (11)	0.0243 (3)
H13	0.8689	0.4629	1.0178	0.029*
C14	0.65719 (17)	0.40446 (13)	0.90988 (10)	0.0195 (3)
H14	0.5996	0.4563	0.9227	0.023*
C15	0.30934 (15)	0.32151 (12)	0.63898 (9)	0.0148 (2)
C16	0.23401 (16)	0.42233 (13)	0.58296 (10)	0.0189 (3)
H16	0.2133	0.4892	0.6084	0.023*
C17	0.18938 (18)	0.42445 (15)	0.48962 (11)	0.0238 (3)
H17	0.1383	0.4929	0.4515	0.029*
C18	0.21944 (18)	0.32687 (15)	0.45237 (11)	0.0241 (3)
H18	0.1895	0.3289	0.3889	0.029*
C19	0.29308 (17)	0.22632 (14)	0.50744 (10)	0.0216 (3)
H19	0.3136	0.1597	0.4817	0.026*
C20	0.33703 (16)	0.22300 (13)	0.60052 (10)	0.0177 (3)
H20	0.3859	0.1535	0.6379	0.021*
P1	0.37156 (4)	0.31925 (3)	0.76149 (2)	0.01286 (8)
Se1	0.270418 (17)	0.457326 (12)	0.793367 (11)	0.01969 (6)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0185 (6)	0.0122 (6)	0.0146 (6)	−0.0004 (5)	0.0119 (5)	−0.0007 (5)
C2	0.0169 (6)	0.0158 (6)	0.0193 (6)	0.0008 (5)	0.0113 (5)	0.0007 (5)
C3	0.0205 (6)	0.0144 (6)	0.0207 (7)	0.0033 (5)	0.0130 (6)	0.0033 (5)
C4	0.0233 (7)	0.0135 (6)	0.0183 (7)	−0.0012 (5)	0.0152 (6)	−0.0012 (5)
C5	0.0188 (6)	0.0190 (7)	0.0160 (6)	−0.0039 (5)	0.0102 (5)	−0.0018 (5)
C6	0.0195 (6)	0.0165 (6)	0.0135 (6)	−0.0002 (5)	0.0094 (5)	0.0010 (5)
C7	0.0278 (7)	0.0178 (7)	0.0266 (8)	−0.0043 (6)	0.0187 (6)	−0.0013 (6)
C8	0.0375 (9)	0.0177 (7)	0.0359 (9)	−0.0010 (6)	0.0271 (8)	0.0024 (6)
C9	0.0162 (6)	0.0147 (6)	0.0138 (6)	−0.0016 (5)	0.0082 (5)	0.0012 (5)
C10	0.0187 (6)	0.0215 (7)	0.0192 (7)	−0.0013 (5)	0.0108 (6)	−0.0024 (5)
C11	0.0188 (7)	0.0267 (8)	0.0235 (7)	0.0011 (6)	0.0127 (6)	0.0033 (6)
C12	0.0172 (6)	0.0288 (8)	0.0204 (7)	−0.0038 (6)	0.0070 (6)	0.0061 (6)
C13	0.0250 (7)	0.0234 (7)	0.0172 (7)	−0.0081 (6)	0.0074 (6)	−0.0018 (6)
C14	0.0236 (7)	0.0165 (6)	0.0170 (7)	−0.0024 (5)	0.0107 (6)	−0.0003 (5)
C15	0.0155 (6)	0.0165 (6)	0.0137 (6)	−0.0023 (5)	0.0091 (5)	0.0004 (5)
C16	0.0179 (6)	0.0190 (7)	0.0194 (7)	−0.0011 (5)	0.0103 (5)	0.0029 (5)
C17	0.0214 (7)	0.0273 (8)	0.0189 (7)	−0.0022 (6)	0.0093 (6)	0.0081 (6)
C18	0.0236 (7)	0.0352 (9)	0.0140 (7)	−0.0090 (6)	0.0110 (6)	0.0006 (6)
C19	0.0241 (7)	0.0269 (7)	0.0179 (7)	−0.0074 (6)	0.0145 (6)	−0.0060 (6)
C20	0.0197 (6)	0.0192 (6)	0.0157 (6)	−0.0024 (5)	0.0108 (5)	−0.0014 (5)
P1	0.01563 (15)	0.01136 (15)	0.01348 (16)	−0.00006 (11)	0.00938 (13)	−0.00031 (12)
Se1	0.02669 (9)	0.01456 (8)	0.02525 (9)	0.00329 (5)	0.01918 (7)	−0.00012 (5)

C1—C2	1.3973 (19)	C11—C12	1.392 (2)
C1—C6	1.4005 (19)	C11—H11	0.95
C1—P1	1.8108 (14)	C12—C13	1.383 (2)
C2—C3	1.392 (2)	C12—H12	0.95
C2—H2	0.95	C13—C14	1.391 (2)
C3—C4	1.397 (2)	C13—H13	0.95
C3—H3	0.95	C14—H14	0.95
C4—C5	1.401 (2)	C15—C20	1.3959 (19)
C4—C7	1.4733 (19)	C15—C16	1.3981 (19)
C5—C6	1.3857 (19)	C15—P1	1.8198 (14)
C5—H5	0.95	C16—C17	1.396 (2)
C6—H6	0.95	C16—H16	0.95
C7—C8	1.322 (2)	C17—C18	1.388 (2)
C7—H7	0.95	C17—H17	0.95
C8—H8A	0.95	C18—C19	1.387 (2)
C8—H8B	0.95	C18—H18	0.95
C9—C14	1.396 (2)	C19—C20	1.394 (2)
C9—C10	1.399 (2)	C19—H19	0.95
C9—P1	1.8173 (14)	C20—H20	0.95
C10—C11	1.387 (2)	P1—Se1	2.1138 (4)
C10—H10	0.95

C2—C1—C6	119.29 (12)	C13—C12—C11	119.86 (14)
C2—C1—P1	122.45 (10)	C13—C12—H12	120.1
C6—C1—P1	118.13 (10)	C11—C12—H12	120.1
C3—C2—C1	120.20 (13)	C12—C13—C14	120.49 (14)
C3—C2—H2	119.9	C12—C13—H13	119.8
C1—C2—H2	119.9	C14—C13—H13	119.8
C2—C3—C4	120.95 (13)	C13—C14—C9	120.00 (14)
C2—C3—H3	119.5	C13—C14—H14	120
C4—C3—H3	119.5	C9—C14—H14	120
C3—C4—C5	118.28 (13)	C20—C15—C16	119.64 (13)
C3—C4—C7	123.00 (13)	C20—C15—P1	120.28 (10)
C5—C4—C7	118.72 (13)	C16—C15—P1	120.07 (11)
C6—C5—C4	121.30 (13)	C17—C16—C15	119.78 (14)
C6—C5—H5	119.4	C17—C16—H16	120.1
C4—C5—H5	119.4	C15—C16—H16	120.1
C5—C6—C1	119.98 (13)	C18—C17—C16	120.19 (14)
C5—C6—H6	120	C18—C17—H17	119.9
C1—C6—H6	120	C16—C17—H17	119.9
C8—C7—C4	126.41 (15)	C19—C18—C17	120.23 (14)
C8—C7—H7	116.8	C19—C18—H18	119.9
C4—C7—H7	116.8	C17—C18—H18	119.9
C7—C8—H8A	120	C18—C19—C20	119.99 (14)
C7—C8—H8B	120	C18—C19—H19	120
H8A—C8—H8B	120	C20—C19—H19	120
C14—C9—C10	119.27 (13)	C19—C20—C15	120.14 (14)
C14—C9—P1	119.62 (11)	C19—C20—H20	119.9
C10—C9—P1	121.08 (11)	C15—C20—H20	119.9
C11—C10—C9	120.29 (14)	C1—P1—C9	105.68 (6)
C11—C10—H10	119.9	C1—P1—C15	104.47 (6)
C9—C10—H10	119.9	C9—P1—C15	107.07 (6)
C10—C11—C12	120.08 (14)	C1—P1—Se1	113.17 (4)
C10—C11—H11	120	C9—P1—Se1	112.96 (5)
C12—C11—H11	120	C15—P1—Se1	112.82 (5)

C6—C1—C2—C3	0.1 (2)	C16—C17—C18—C19	0.4 (2)
P1—C1—C2—C3	175.86 (11)	C17—C18—C19—C20	0.1 (2)
C1—C2—C3—C4	−0.7 (2)	C18—C19—C20—C15	−1.0 (2)
C2—C3—C4—C5	0.9 (2)	C16—C15—C20—C19	1.5 (2)
C2—C3—C4—C7	−178.22 (14)	P1—C15—C20—C19	−178.21 (11)
C3—C4—C5—C6	−0.6 (2)	C2—C1—P1—C9	14.26 (13)
C7—C4—C5—C6	178.61 (13)	C6—C1—P1—C9	−169.95 (11)
C4—C5—C6—C1	0.0 (2)	C2—C1—P1—C15	127.04 (12)
C2—C1—C6—C5	0.2 (2)	C6—C1—P1—C15	−57.17 (12)
P1—C1—C6—C5	−175.69 (11)	C2—C1—P1—Se1	−109.86 (11)
C3—C4—C7—C8	−4.9 (2)	C6—C1—P1—Se1	65.93 (11)
C5—C4—C7—C8	175.95 (16)	C14—C9—P1—C1	−115.72 (12)
C14—C9—C10—C11	0.8 (2)	C10—C9—P1—C1	62.47 (13)
P1—C9—C10—C11	−177.41 (11)	C14—C9—P1—C15	133.33 (11)
C9—C10—C11—C12	−1.0 (2)	C10—C9—P1—C15	−48.48 (13)
C10—C11—C12—C13	0.0 (2)	C14—C9—P1—Se1	8.54 (13)
C11—C12—C13—C14	1.1 (2)	C10—C9—P1—Se1	−173.27 (10)
C12—C13—C14—C9	−1.3 (2)	C20—C15—P1—C1	−42.60 (12)
C10—C9—C14—C13	0.4 (2)	C16—C15—P1—C1	137.66 (11)
P1—C9—C14—C13	178.59 (11)	C20—C15—P1—C9	69.18 (12)
C20—C15—C16—C17	−1.0 (2)	C16—C15—P1—C9	−110.55 (11)
P1—C15—C16—C17	178.70 (11)	C20—C15—P1—Se1	−165.94 (10)
C15—C16—C17—C18	0.1 (2)	C16—C15—P1—Se1	14.33 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg1ⁱ	0.95	2.62	3.383 (2)	137
C3—H3···Cg2ⁱⁱ	0.95	2.88	3.5889 (19)	133
C12—H12···Cg2ⁱⁱⁱ	0.95	2.85	3.614 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯Cg1ⁱ	0.95	2.62	3.383 (2)	137
C3—H3⋯Cg2ⁱⁱ	0.95	2.88	3.5889 (19)	133
C12—H12⋯Cg2ⁱⁱⁱ	0.95	2.85	3.614 (2)	138

Symmetry codes: (i) ; (ii) ; (iii) .

3 in total

(4-Ethenylphen-yl)diphenyl-phosphine selenide.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. trans-Chloro(methyl)bis(tricyclohexylphosphine)platinum(II).

2. A short history of SHELX.

3. Rapid phosphorus(III) ligand evaluation utilising potassium selenocyanate.