Dicyclo-hex-yl(4-isopropyl-phen-yl)phosphane selenide.

In the title compund, C(21)H(33)PSe, the Se=P bond is part of a distorted tetra-hedral environment on the P atom. Both cyclo-hexyl groups adopt chair conformations. A cone angle of 170° was calculated using an adaptation of the Tolman model. Inter-molecular C-H⋯Se and C-H⋯Cg contacts are observed (Cg is the centroid of the benzene ring).

Related literature

For background studies aimed at understanding the transition metal–phospho­rus bond, see: Muller et al. (2008 ▶); Roodt et al. (2003 ▶). For transition metal complexes with PCy2(4-Pr—C6H4), see: Makhoba et al. (2011 ▶); Vuba & Muller (2012 ▶). For background to cone angles, see: Tolman (1977 ▶).

Experimental

Crystal data

C21H33PSe

M = 395.4

Monoclinic,

a = 13.1311 (10) Å

b = 13.6991 (10) Å

c = 11.7821 (8) Å

β = 103.106 (2)°

V = 2064.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.90 mm−1

T = 100 K

0.22 × 0.14 × 0.1 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.681, T max = 0.833

28000 measured reflections

5140 independent reflections

4397 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.057

S = 1.02

5140 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.24 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: SIR97 (Altomare et al., 1999 ▶); 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/S1600536812004643/kp2386sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004643/kp2386Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004643/kp2386Isup3.cml

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

C21H33PSe	F(000) = 832
Mr = 395.4	Dx = 1.272 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8561 reflections
a = 13.1311 (10) Å	θ = 2.3–28.2°
b = 13.6991 (10) Å	µ = 1.90 mm−1
c = 11.7821 (8) Å	T = 100 K
β = 103.106 (2)°	Cuboid, colourless
V = 2064.2 (3) Å3	0.22 × 0.14 × 0.1 mm
Z = 4

Bruker APEX DUO 4K CCD diffractometer	5140 independent reflections
Graphite monochromator	4397 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1	Rint = 0.040
φ and ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
Tmin = 0.681, Tmax = 0.833	k = −18→18
28000 measured reflections	l = −15→15

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0262P)2 + 0.6415P] where P = (Fo2 + 2Fc2)/3
5140 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The intensity data was collected on a Bruker Apex DUO 4K CCD diffractometer using an exposure time of 10 s/frame. A total of 5967 frames were collected with a frame width of 0.5° covering up to θ = 28.31° with 100% completeness accomplished.Analytical data: 31P {H} NMR (CDCl3, 160 MHz): δ = 54.1 (s, 1P)

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
P1	0.63459 (3)	0.16154 (3)	0.07287 (3)	0.01280 (8)
Se1	0.589654 (11)	0.097347 (10)	0.218666 (12)	0.01702 (5)
C1	0.53424 (10)	0.24106 (10)	−0.01384 (12)	0.0147 (3)
H1	0.564	0.2718	−0.0762	0.018*
C2	0.43736 (11)	0.18232 (11)	−0.07302 (13)	0.0193 (3)
H2A	0.4569	0.1344	−0.1272	0.023*
H2B	0.4107	0.1458	−0.0132	0.023*
C3	0.35114 (11)	0.24925 (11)	−0.14041 (14)	0.0228 (3)
H3A	0.375	0.2799	−0.206	0.027*
H3B	0.2881	0.2099	−0.1733	0.027*
C4	0.32313 (12)	0.32877 (12)	−0.06224 (15)	0.0239 (3)
H4A	0.2693	0.3722	−0.1089	0.029*
H4B	0.2936	0.2985	−0.0005	0.029*
C5	0.41921 (12)	0.38870 (11)	−0.00652 (14)	0.0222 (3)
H5A	0.3998	0.4382	0.046	0.027*
H5B	0.4452	0.4234	−0.068	0.027*
C6	0.50595 (11)	0.32336 (11)	0.06286 (13)	0.0193 (3)
H6A	0.4826	0.2944	0.1296	0.023*
H6B	0.5688	0.3634	0.0942	0.023*
C7	0.66780 (10)	0.06797 (10)	−0.02535 (12)	0.0139 (3)
H7	0.6056	0.0244	−0.0499	0.017*
C8	0.69309 (11)	0.11074 (10)	−0.13626 (13)	0.0174 (3)
H8A	0.6317	0.1473	−0.1804	0.021*
H8B	0.7523	0.157	−0.1145	0.021*
C9	0.72156 (12)	0.02992 (11)	−0.21352 (13)	0.0198 (3)
H9A	0.6606	−0.0136	−0.24	0.024*
H9B	0.7393	0.0594	−0.2833	0.024*
C10	0.81410 (12)	−0.02969 (11)	−0.14730 (13)	0.0205 (3)
H10A	0.8764	0.0128	−0.1253	0.025*
H10B	0.8301	−0.0824	−0.1981	0.025*
C11	0.78950 (12)	−0.07406 (11)	−0.03796 (13)	0.0206 (3)
H11A	0.8515	−0.11	0.0058	0.025*
H11B	0.7313	−0.1213	−0.0606	0.025*
C12	0.75906 (11)	0.00468 (10)	0.04060 (12)	0.0173 (3)
H12A	0.8203	0.0469	0.0712	0.021*
H12B	0.7388	−0.0269	0.1078	0.021*
C13	0.75153 (10)	0.23630 (10)	0.11383 (12)	0.0137 (3)
C14	0.77795 (11)	0.30400 (10)	0.03631 (12)	0.0159 (3)
H14	0.7302	0.3173	−0.0356	0.019*
C15	0.87363 (11)	0.35183 (10)	0.06399 (13)	0.0171 (3)
H15	0.8906	0.3976	0.0106	0.021*
C16	0.94567 (10)	0.33377 (10)	0.16937 (12)	0.0160 (3)
C17	0.91711 (11)	0.26870 (10)	0.24719 (13)	0.0167 (3)
H17	0.9639	0.2567	0.3201	0.02*
C18	0.82115 (11)	0.22069 (10)	0.22028 (12)	0.0150 (3)
H18	0.8031	0.1769	0.2751	0.018*
C19	1.05187 (11)	0.38265 (11)	0.19607 (13)	0.0193 (3)
H19	1.0879	0.3646	0.2775	0.023*
C20	1.11914 (12)	0.34511 (13)	0.11461 (15)	0.0278 (4)
H20A	1.1266	0.2741	0.1225	0.042*
H20B	1.1884	0.3757	0.1354	0.042*
H20C	1.0855	0.3616	0.0339	0.042*
C21	1.04331 (12)	0.49378 (11)	0.19028 (14)	0.0241 (3)
H21A	1.0042	0.5134	0.1126	0.036*
H21B	1.1135	0.5223	0.2055	0.036*
H21C	1.0068	0.5169	0.249	0.036*

	U11	U22	U33	U12	U13	U23
P1	0.01478 (16)	0.01252 (16)	0.01143 (17)	−0.00245 (12)	0.00365 (13)	−0.00016 (13)
Se1	0.02188 (8)	0.01700 (8)	0.01373 (8)	−0.00395 (6)	0.00727 (5)	0.00076 (5)
C1	0.0143 (6)	0.0151 (7)	0.0144 (7)	−0.0018 (5)	0.0029 (5)	0.0004 (5)
C2	0.0165 (6)	0.0179 (7)	0.0223 (8)	−0.0026 (5)	0.0017 (6)	−0.0022 (6)
C3	0.0170 (7)	0.0237 (8)	0.0247 (8)	−0.0027 (6)	−0.0014 (6)	0.0017 (6)
C4	0.0187 (7)	0.0245 (8)	0.0288 (9)	0.0034 (6)	0.0064 (6)	0.0064 (7)
C5	0.0246 (7)	0.0176 (7)	0.0244 (8)	0.0027 (6)	0.0054 (6)	0.0019 (6)
C6	0.0215 (7)	0.0169 (7)	0.0191 (8)	0.0009 (5)	0.0040 (6)	−0.0019 (6)
C7	0.0162 (6)	0.0125 (6)	0.0130 (7)	−0.0018 (5)	0.0037 (5)	−0.0012 (5)
C8	0.0224 (7)	0.0164 (7)	0.0142 (7)	0.0010 (5)	0.0060 (6)	0.0011 (5)
C9	0.0278 (7)	0.0193 (7)	0.0135 (7)	0.0011 (6)	0.0075 (6)	0.0000 (6)
C10	0.0236 (7)	0.0199 (7)	0.0200 (8)	0.0008 (6)	0.0092 (6)	−0.0022 (6)
C11	0.0261 (7)	0.0176 (7)	0.0195 (8)	0.0038 (6)	0.0082 (6)	0.0008 (6)
C12	0.0211 (7)	0.0179 (7)	0.0131 (7)	0.0024 (5)	0.0041 (5)	0.0019 (5)
C13	0.0150 (6)	0.0127 (6)	0.0134 (7)	−0.0014 (5)	0.0037 (5)	−0.0030 (5)
C14	0.0177 (6)	0.0173 (7)	0.0118 (7)	−0.0018 (5)	0.0011 (5)	0.0003 (5)
C15	0.0199 (7)	0.0169 (7)	0.0149 (7)	−0.0044 (5)	0.0047 (5)	0.0020 (5)
C16	0.0155 (6)	0.0151 (6)	0.0168 (7)	−0.0019 (5)	0.0027 (5)	−0.0030 (5)
C17	0.0173 (6)	0.0170 (7)	0.0145 (7)	0.0005 (5)	0.0009 (5)	−0.0002 (5)
C18	0.0191 (6)	0.0125 (6)	0.0136 (7)	0.0005 (5)	0.0044 (5)	0.0003 (5)
C19	0.0165 (6)	0.0234 (8)	0.0165 (7)	−0.0047 (6)	0.0010 (5)	0.0004 (6)
C20	0.0186 (7)	0.0364 (9)	0.0290 (9)	0.0006 (6)	0.0064 (6)	−0.0011 (7)
C21	0.0236 (7)	0.0239 (8)	0.0243 (8)	−0.0089 (6)	0.0045 (6)	−0.0019 (6)

P1—C13	1.8176 (13)	C9—H9B	0.99
P1—C1	1.8321 (14)	C10—C11	1.524 (2)
P1—C7	1.8442 (14)	C10—H10A	0.99
P1—Se1	2.1288 (4)	C10—H10B	0.99
C1—C2	1.5329 (18)	C11—C12	1.532 (2)
C1—C6	1.5421 (19)	C11—H11A	0.99
C1—H1	1	C11—H11B	0.99
C2—C3	1.531 (2)	C12—H12A	0.99
C2—H2A	0.99	C12—H12B	0.99
C2—H2B	0.99	C13—C18	1.3908 (19)
C3—C4	1.524 (2)	C13—C14	1.3994 (19)
C3—H3A	0.99	C14—C15	1.3886 (19)
C3—H3B	0.99	C14—H14	0.95
C4—C5	1.524 (2)	C15—C16	1.4018 (19)
C4—H4A	0.99	C15—H15	0.95
C4—H4B	0.99	C16—C17	1.390 (2)
C5—C6	1.531 (2)	C16—C19	1.5143 (19)
C5—H5A	0.99	C17—C18	1.3928 (19)
C5—H5B	0.99	C17—H17	0.95
C6—H6A	0.99	C18—H18	0.95
C6—H6B	0.99	C19—C21	1.527 (2)
C7—C8	1.536 (2)	C19—C20	1.533 (2)
C7—C12	1.5392 (19)	C19—H19	1
C7—H7	1	C20—H20A	0.98
C8—C9	1.533 (2)	C20—H20B	0.98
C8—H8A	0.99	C20—H20C	0.98
C8—H8B	0.99	C21—H21A	0.98
C9—C10	1.524 (2)	C21—H21B	0.98
C9—H9A	0.99	C21—H21C	0.98
C13—P1—C1	105.70 (6)	C10—C9—H9B	109.5
C13—P1—C7	104.63 (6)	C8—C9—H9B	109.5
C1—P1—C7	107.81 (6)	H9A—C9—H9B	108
C13—P1—Se1	112.99 (5)	C9—C10—C11	110.45 (12)
C1—P1—Se1	113.56 (5)	C9—C10—H10A	109.6
C7—P1—Se1	111.56 (5)	C11—C10—H10A	109.6
C2—C1—C6	111.41 (11)	C9—C10—H10B	109.6
C2—C1—P1	111.05 (10)	C11—C10—H10B	109.6
C6—C1—P1	110.26 (10)	H10A—C10—H10B	108.1
C2—C1—H1	108	C10—C11—C12	111.36 (12)
C6—C1—H1	108	C10—C11—H11A	109.4
P1—C1—H1	108	C12—C11—H11A	109.4
C3—C2—C1	111.18 (12)	C10—C11—H11B	109.4
C3—C2—H2A	109.4	C12—C11—H11B	109.4
C1—C2—H2A	109.4	H11A—C11—H11B	108
C3—C2—H2B	109.4	C11—C12—C7	111.80 (12)
C1—C2—H2B	109.4	C11—C12—H12A	109.3
H2A—C2—H2B	108	C7—C12—H12A	109.3
C4—C3—C2	111.46 (13)	C11—C12—H12B	109.3
C4—C3—H3A	109.3	C7—C12—H12B	109.3
C2—C3—H3A	109.3	H12A—C12—H12B	107.9
C4—C3—H3B	109.3	C18—C13—C14	118.74 (12)
C2—C3—H3B	109.3	C18—C13—P1	119.72 (11)
H3A—C3—H3B	108	C14—C13—P1	121.31 (10)
C5—C4—C3	110.84 (12)	C15—C14—C13	120.29 (13)
C5—C4—H4A	109.5	C15—C14—H14	119.9
C3—C4—H4A	109.5	C13—C14—H14	119.9
C5—C4—H4B	109.5	C14—C15—C16	121.17 (13)
C3—C4—H4B	109.5	C14—C15—H15	119.4
H4A—C4—H4B	108.1	C16—C15—H15	119.4
C4—C5—C6	110.98 (12)	C17—C16—C15	117.95 (13)
C4—C5—H5A	109.4	C17—C16—C19	121.34 (13)
C6—C5—H5A	109.4	C15—C16—C19	120.70 (13)
C4—C5—H5B	109.4	C16—C17—C18	121.21 (13)
C6—C5—H5B	109.4	C16—C17—H17	119.4
H5A—C5—H5B	108	C18—C17—H17	119.4
C5—C6—C1	111.31 (12)	C13—C18—C17	120.56 (13)
C5—C6—H6A	109.4	C13—C18—H18	119.7
C1—C6—H6A	109.4	C17—C18—H18	119.7
C5—C6—H6B	109.4	C16—C19—C21	112.13 (12)
C1—C6—H6B	109.4	C16—C19—C20	110.84 (12)
H6A—C6—H6B	108	C21—C19—C20	110.70 (13)
C8—C7—C12	110.53 (11)	C16—C19—H19	107.7
C8—C7—P1	113.34 (9)	C21—C19—H19	107.7
C12—C7—P1	110.03 (9)	C20—C19—H19	107.7
C8—C7—H7	107.6	C19—C20—H20A	109.5
C12—C7—H7	107.6	C19—C20—H20B	109.5
P1—C7—H7	107.6	H20A—C20—H20B	109.5
C9—C8—C7	111.02 (11)	C19—C20—H20C	109.5
C9—C8—H8A	109.4	H20A—C20—H20C	109.5
C7—C8—H8A	109.4	H20B—C20—H20C	109.5
C9—C8—H8B	109.4	C19—C21—H21A	109.5
C7—C8—H8B	109.4	C19—C21—H21B	109.5
H8A—C8—H8B	108	H21A—C21—H21B	109.5
C10—C9—C8	110.89 (12)	C19—C21—H21C	109.5
C10—C9—H9A	109.5	H21A—C21—H21C	109.5
C8—C9—H9A	109.5	H21B—C21—H21C	109.5
C13—P1—C1—C2	169.50 (10)	C9—C10—C11—C12	−56.47 (16)
C7—P1—C1—C2	58.04 (11)	C10—C11—C12—C7	54.94 (16)
Se1—P1—C1—C2	−66.09 (11)	C8—C7—C12—C11	−53.92 (15)
C13—P1—C1—C6	−66.51 (11)	P1—C7—C12—C11	−179.86 (10)
C7—P1—C1—C6	−177.97 (9)	C1—P1—C13—C18	147.20 (11)
Se1—P1—C1—C6	57.90 (10)	C7—P1—C13—C18	−99.12 (12)
C6—C1—C2—C3	53.72 (17)	Se1—P1—C13—C18	22.43 (13)
P1—C1—C2—C3	177.05 (10)	C1—P1—C13—C14	−38.34 (13)
C1—C2—C3—C4	−55.38 (17)	C7—P1—C13—C14	75.35 (13)
C2—C3—C4—C5	57.02 (17)	Se1—P1—C13—C14	−163.10 (10)
C3—C4—C5—C6	−57.05 (17)	C18—C13—C14—C15	2.3 (2)
C4—C5—C6—C1	55.67 (17)	P1—C13—C14—C15	−172.26 (11)
C2—C1—C6—C5	−54.09 (16)	C13—C14—C15—C16	0.0 (2)
P1—C1—C6—C5	−177.88 (10)	C14—C15—C16—C17	−2.0 (2)
C13—P1—C7—C8	−61.65 (11)	C14—C15—C16—C19	177.00 (13)
C1—P1—C7—C8	50.53 (11)	C15—C16—C17—C18	1.8 (2)
Se1—P1—C7—C8	175.86 (8)	C19—C16—C17—C18	−177.24 (13)
C13—P1—C7—C12	62.67 (11)	C14—C13—C18—C17	−2.5 (2)
C1—P1—C7—C12	174.85 (9)	P1—C13—C18—C17	172.11 (11)
Se1—P1—C7—C12	−59.81 (10)	C16—C17—C18—C13	0.5 (2)
C12—C7—C8—C9	55.13 (15)	C17—C16—C19—C21	−124.22 (15)
P1—C7—C8—C9	179.19 (10)	C15—C16—C19—C21	56.82 (19)
C7—C8—C9—C10	−57.63 (16)	C17—C16—C19—C20	111.50 (16)
C8—C9—C10—C11	57.88 (16)	C15—C16—C19—C20	−67.46 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Se1i	1.00	3.09	4.0500 (14)	162
C9—H9B···Cg1ii	0.99	2.81	3.6471	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Se1i	1.00	3.09	4.0500 (14)	162
C9—H9B⋯Cg1ii	0.99	2.81	3.6471	143

Symmetry codes: (i) ; (ii) .