Dicyclo­hex­yl(4-isopropyl­phen­yl)phosphane selenide

Makhoba, S.; Muller, A.; Phasha, Z.

doi:10.1107/S1600536812004643

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o648

doi:10.1107/S1600536812004643

Open

access

Dicyclohexyl(4-isopropylphenyl)phosphane selenide

Sizwe Makhoba,^a Alfred Muller ^a ^* and Zanele Phasha ^a

^aResearch Center for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park, Johannesburg 2006, South Africa
^*Correspondence e-mail: mullera@uj.ac.za

(Received 25 January 2012; accepted 3 February 2012; online 10 February 2012)

In the title compund, C₂₁H₃₃PSe, the Se=P bond is part of a distorted tetrahedral environment on the P atom. Both cyclohexyl groups adopt chair conformations. A cone angle of 170° was calculated using an adaptation of the Tolman model. Intermolecular 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-ⁱPr—C₆H₄), see: Makhoba et al. (2011 ); Vuba & Muller (2012 ). For background to cone angles, see: Tolman (1977 ).

Experimental

Crystal data

C₂₁H₃₃PSe
M_r = 395.4
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.023
wR(F²) = 0.057
S = 1.02
5140 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812004643/kp2386sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812004643/kp2386Isup3.cml

checkCIF report

Comment top

The bonding of phosphorus to transitional metals have being investigated extensively, with several attempts to divide the properties of the phosphorus ligand into steric and electronic effects. Various techniques such as single-crystal X-ray crystallography, multi nuclear NMR and IR (Roodt et al., 2003) have been used to this extent. Recently we have also included selenium derivatives of the phosphorus compounds into this study (Muller et al., 2008). This route seems viable as the use of expensive transition metals and steric influence from other ligands in the coordination sphere are eliminated, leaving only crystal packing effects as an additional influence on the steric property of the phosphorus ligand. As part of this investigation we report here the selenium derivative of PCy₂(4-ⁱPr—C₆H₄) where Cy = cyclohexyl and ⁱPr = isopropyl.

Molecules of the title compound (Fig. 1) adopts a distorted tetrahedral arrangement about the P atom with average C—P—C and Se—P—C angles of 106.0° and 112.7° respectively. The cone angle was found to be 170° when the Se—P distance was adjusted to 2.28 Å (the default value from Tolman, 1977). This value is ca 5° larger than previous reported values where the present phosphine was bonded to a transition metal centre (Makhoba et al., 2011; Vuba & Muller, 2012). This indicates to some extend the flexibility of this phosphine ligand and its ability to use space to enable less crowding of its substituents. Weak intermolecular C—H···Se and C—H···Cg contacts are observed (Table 1, Fig. 2) and link the molecules as infinite chains in the [001] direction.

Related literature top

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-ⁱPr—C₆H₄), see: Makhoba et al. (2011); Vuba & Muller (2012). For background to cone angles, see: Tolman (1977).

Experimental top

KSeCN (10 mg, 0.0694 mmol) and PCy₂(4-ⁱPr—C₆H₄) (21.96 mg, 0.0694 mmol) were both dissolved in a minimum amount of methanol (10–20 ml). The KSeCN solution was added drop wise (5 min) to the phosphine solution while stirring at room temperature. The final solution was left to evaporate slowly in order to give crystals that are suitable for single-crystal X-ray study.

Computing details top

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).

Figures top

	Fig. 1. A view of the title compound showing the numbering scheme of atoms and displacement ellipsoids (drawn at the 50% probability level). H atoms omitted for clarity.
	Fig. 2. Packing diagram showing the interactions observed for the structure.

Dicyclohexyl(4-isopropylphenyl)phosphane selenide top

Crystal data top

C₂₁H₃₃PSe	F(000) = 832
M_r = 395.4	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0262P)² + 0.6415P] where P = (F_o² + 2F_c²)/3
5140 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₃₃PSe	V = 2064.2 (3) Å³
M_r = 395.4	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.1311 (10) Å	µ = 1.90 mm⁻¹
b = 13.6991 (10) Å	T = 100 K
c = 11.7821 (8) Å	0.22 × 0.14 × 0.1 mm
β = 103.106 (2)°

Data collection top

Bruker APEX DUO 4K CCD diffractometer	5140 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4397 reflections with I > 2σ(I)
T_min = 0.681, T_max = 0.833	R_int = 0.040
28000 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.02	Δρ_max = 0.41 e Å⁻³
5140 reflections	Δρ_min = −0.24 e Å⁻³
210 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2; (ii) x, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₃₃PSe
M_r	395.4
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.1311 (10), 13.6991 (10), 11.7821 (8)
β (°)	103.106 (2)
V (Å³)	2064.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.90
Crystal size (mm)	0.22 × 0.14 × 0.1

Data collection
Diffractometer	Bruker APEX DUO 4K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.681, 0.833
No. of measured, independent and observed [I > 2σ(I)] reflections	28000, 5140, 4397
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.057, 1.02
No. of reflections	5140
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.24

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2008), SAINT and XPREP (Bruker, 2008), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2; (ii) x, −y−1/2, z−3/2.

Acknowledgements

Research funding from the University of Johannesburg is gratefully acknowledged.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Makhoba, S., Muller, A., Meijboom, R. & Omondi, B. (2011). Acta Cryst. E67, m1286–m1287. Web of Science CSD CrossRef IUCr Journals Google Scholar
Muller, A., Meijboom, R. & Roodt, A. (2008). Dalton Trans. pp. 650–657. Web of Science CSD CrossRef Google Scholar
Roodt, A., Otto, S. & Steyl, G. J. (2003). Coord. Chem. Rev. 245, 121–137. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tolman, C. A. (1977). Chem. Rev. 77, 313–348. CrossRef CAS Web of Science Google Scholar
Vuba, B. & Muller, A. (2012). Acta Cryst. E68, m14–m15. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o648

doi:10.1107/S1600536812004643

Open

access