Dicyclo­hex­yl[4-(dimethyl­amino)­phen­yl]phosphine selenide

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

doi:10.1107/S1600536811054006

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o243

doi:10.1107/S1600536811054006

Open

access

Dicyclohexyl[4-(dimethylamino)phenyl]phosphine selenide

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

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

(Received 25 November 2011; accepted 15 December 2011; online 23 December 2011)

In the title molecule, C₂₀H₃₂NPSe, the P atom has a distorted tetrahedral environment resulting in an effective cone angle of 172°. Weak intermolecular C—H⋯Se interactions are observed.

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 on cone angles, see: Bunten et al. (2002 ); Tolman (1977 ); Otto (2001 ).

Experimental

Crystal data

C₂₀H₃₂NPSe
M_r = 396.4
Monoclinic, P 2₁ /c
a = 12.3860 (16) Å
b = 6.8331 (8) Å
c = 24.113 (3) Å
β = 97.050 (3)°
V = 2025.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.93 mm⁻¹
T = 100 K
0.29 × 0.12 × 0.05 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.604, T_max = 0.910
31168 measured reflections
5008 independent reflections
4192 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.063
S = 1.02
5008 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯Se1ⁱ	1.00	2.71	3.6546 (15)	157
C19—H19A⋯Se1ⁱ	0.99	3.04	3.8836 (18)	143
Symmetry code: (i) x, y+1, z.

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/S1600536811054006/nc2259sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054006/nc2259Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054006/nc2259Isup3.cml

checkCIF report

Comment top

The study of the transition metal phosphorous bond spans over several decades using various techniques such as crystallography, multi nuclear NMR and IR (Roodt et al., 2003). As part of this systematic investigation we have extended this study to selenium derivatives of the phosphorus ligands (see Muller et al., 2008). This way there is no steric crowding effect, albeit crystal packing effects, as normally found in transition metal complexes with bulky ligands, e.g. in trans-[Rh(CO)Cl{P(OC₆H₅)₃}₂] cone angles variation from 156° to 167° was observed for the two phosphite ligands (Muller et al., 2006). The ¹J(³¹P-⁷⁷Se) coupling can also be used as an additional probe to obtain more information regarding the nature of the phosphorous bond. Reported as part of the above continuing study, the single-crystal structure of the phosphorus containing compound, SePCy₂(4-N{CH₃}₂-C₆H₄) where Cy = C₆H₁₁, is reported here.

Molecules of the title compound (see Fig. 1) adopts a distorted tetrahedral arrangement about phosphorous atom with average C—P—C and Se—P—C angles of 107.1° and 111.9° respectively. Describing the steric demand of phosphane ligands has been the topic of many studies and a variety of models have been developed (Bunten et al., 2002). The Tolman cone angle (Tolman, 1977) is still the most commonly used model. Applying this model to the geometry obtained for the title compound (and adjusting the Se—P bond distance to 2.28 Å) we calculated an effective cone angle (Otto, 2001) of 171.5°. Weak intermolecular C—H···Se interactions (Table 1) are observed in the crystal lattice.

Related literature top

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 on cone angles, see: Bunten et al. (2002); Tolman (1977); Otto (2001).

Experimental top

Dicyclohexyl(4-(N,N-dimethylamino)phenyl)phosphine and KSeCN were purchased from Sigma-Aldrich and used without purification. Eqimolar amounts of KSeCN (5.8 mg, 0.04 mmol) and the dicyclohexyl(4-(N,N-dimethylamino)phenyl)phosphine (11.5 mg, 0.04 mmol) were dissolved in the minimum amounts of methanol (10 ml). The KSeCN solution was added drop wise (5 min.) to the phosphine solution with stirring at room temperature. The final solution was left to evaporate slowly until dry to give crystals suitable for a 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. : View of the title compound with labelling and displacement ellipsoids drawn at a 50% probability level.

Dicyclohexyl[4-(dimethylamino)phenyl]phosphine selenide top

Crystal data top

C₂₀H₃₂NPSe	F(000) = 832
M_r = 396.4	D_x = 1.3 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9647 reflections
a = 12.3860 (16) Å	θ = 2.2–28.2°
b = 6.8331 (8) Å	µ = 1.93 mm⁻¹
c = 24.113 (3) Å	T = 100 K
β = 97.050 (3)°	Plate, colourless
V = 2025.3 (4) Å³	0.29 × 0.12 × 0.05 mm
Z = 4

Data collection top

Bruker APEX DUO 4K CCD diffractometer	5008 independent reflections
Graphite monochromator	4192 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm^-1	R_int = 0.033
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
T_min = 0.604, T_max = 0.910	k = −9→7
31168 measured reflections	l = −32→32

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0282P)² + 1.2459P] where P = (F_o² + 2F_c²)/3
5008 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₀H₃₂NPSe	V = 2025.3 (4) Å³
M_r = 396.4	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3860 (16) Å	µ = 1.93 mm⁻¹
b = 6.8331 (8) Å	T = 100 K
c = 24.113 (3) Å	0.29 × 0.12 × 0.05 mm
β = 97.050 (3)°

Data collection top

Bruker APEX DUO 4K CCD diffractometer	5008 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4192 reflections with I > 2σ(I)
T_min = 0.604, T_max = 0.910	R_int = 0.033
31168 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.02	Δρ_max = 0.53 e Å⁻³
5008 reflections	Δρ_min = −0.24 e Å⁻³
210 parameters

Special details top

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 30 s/frame. A total of 1671 frames were collected with a frame width of 0.5° covering up to θ = 28.29° with 99.8% completeness accomplished. Analytical data: ¹H NMR (CDCl₃, 400 MHz) δ 7.68, 6.69 (m, 4H), 2.99 (s, 6H), 2.19–1.13 (m, 22H); ¹³C {H} NMR (CDCl₃, 100 MHz) δ 152.2, 134.2, 111.0 (Ar); 40.0 (Me); 36.72, 26.36 (Cy); ³¹P {H} NMR (CDCl₃, 160 MHz):δ = 52.9 (t, ¹J_Se—P = 687 Hz, 1P).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Se1	0.198411 (13)	0.25268 (2)	0.085698 (7)	0.01880 (5)
P1	0.17385 (3)	0.54119 (5)	0.114465 (16)	0.01278 (8)
C2	0.30292 (12)	0.4535 (2)	0.21383 (6)	0.0180 (3)
H2	0.2882	0.3209	0.2037	0.022*
N1	0.45558 (12)	0.7312 (2)	0.32915 (6)	0.0252 (3)
C1	0.26027 (12)	0.6017 (2)	0.17787 (6)	0.0139 (3)
C3	0.36616 (13)	0.4943 (2)	0.26382 (7)	0.0198 (3)
H3	0.3931	0.3898	0.2876	0.024*
C4	0.39116 (12)	0.6884 (2)	0.28002 (6)	0.0179 (3)
C5	0.34835 (12)	0.8385 (2)	0.24342 (6)	0.0175 (3)
H5	0.3638	0.9713	0.2531	0.021*
C6	0.28439 (12)	0.7956 (2)	0.19382 (6)	0.0149 (3)
H6	0.2563	0.8994	0.1701	0.018*
C7	0.46054 (15)	0.9295 (3)	0.35068 (7)	0.0279 (4)
H7A	0.4903	1.0163	0.324	0.042*
H7B	0.5074	0.9331	0.3865	0.042*
H7C	0.3872	0.9732	0.3561	0.042*
C8	0.49523 (14)	0.5753 (3)	0.36689 (7)	0.0269 (4)
H8A	0.4342	0.5178	0.3835	0.04*
H8B	0.5485	0.6281	0.3965	0.04*
H8C	0.5298	0.4744	0.3462	0.04*
C9	0.03310 (12)	0.5742 (2)	0.12921 (6)	0.0144 (3)
H9	−0.0153	0.5443	0.0939	0.017*
C10	0.00619 (13)	0.7830 (2)	0.14649 (7)	0.0189 (3)
H10A	0.0529	0.8187	0.1813	0.023*
H10B	0.0212	0.8761	0.1169	0.023*
C11	−0.11370 (13)	0.7973 (3)	0.15585 (8)	0.0242 (4)
H11A	−0.1286	0.9305	0.1692	0.029*
H11B	−0.16	0.7763	0.1199	0.029*
C12	−0.14340 (14)	0.6474 (3)	0.19833 (7)	0.0234 (3)
H12A	−0.2224	0.6548	0.201	0.028*
H12B	−0.1042	0.6788	0.2355	0.028*
C13	−0.11435 (13)	0.4399 (2)	0.18195 (7)	0.0201 (3)
H13A	−0.1602	0.4021	0.147	0.024*
H13B	−0.1295	0.3475	0.2117	0.024*
C14	0.00578 (12)	0.4261 (2)	0.17331 (6)	0.0178 (3)
H14A	0.022	0.2921	0.1611	0.021*
H14B	0.0517	0.4522	0.2091	0.021*
C15	0.19907 (12)	0.7244 (2)	0.06209 (6)	0.0138 (3)
H15	0.1885	0.8568	0.0783	0.017*
C16	0.11808 (12)	0.7031 (2)	0.00891 (6)	0.0170 (3)
H16A	0.1222	0.5685	−0.0059	0.02*
H16B	0.0433	0.7244	0.0182	0.02*
C17	0.14214 (13)	0.8499 (2)	−0.03583 (6)	0.0194 (3)
H17A	0.0914	0.8273	−0.0703	0.023*
H17B	0.1301	0.9844	−0.0226	0.023*
C18	0.25890 (13)	0.8306 (3)	−0.04903 (7)	0.0236 (3)
H18A	0.2694	0.6997	−0.0651	0.028*
H18B	0.2729	0.9302	−0.0771	0.028*
C19	0.33917 (13)	0.8580 (3)	0.00356 (7)	0.0211 (3)
H19A	0.3329	0.9928	0.0179	0.025*
H19B	0.4143	0.84	−0.0056	0.025*
C20	0.31696 (12)	0.7111 (2)	0.04871 (6)	0.0172 (3)
H20A	0.3673	0.7367	0.0831	0.021*
H20B	0.3312	0.577	0.0359	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.02229 (8)	0.00922 (8)	0.02423 (9)	0.00091 (6)	0.00027 (6)	−0.00182 (6)
P1	0.01404 (17)	0.00898 (16)	0.01457 (17)	−0.00026 (14)	−0.00125 (13)	0.00036 (14)
C2	0.0184 (7)	0.0145 (7)	0.0201 (7)	−0.0009 (6)	−0.0014 (6)	0.0038 (6)
N1	0.0244 (7)	0.0300 (8)	0.0187 (7)	−0.0028 (6)	−0.0079 (5)	0.0012 (6)
C1	0.0128 (6)	0.0141 (7)	0.0143 (7)	−0.0005 (5)	−0.0009 (5)	0.0011 (6)
C3	0.0185 (7)	0.0208 (8)	0.0190 (7)	0.0004 (6)	−0.0020 (6)	0.0064 (6)
C4	0.0124 (7)	0.0253 (8)	0.0153 (7)	−0.0016 (6)	−0.0014 (5)	0.0014 (6)
C5	0.0168 (7)	0.0160 (7)	0.0191 (7)	−0.0021 (6)	0.0001 (6)	−0.0008 (6)
C6	0.0145 (7)	0.0143 (7)	0.0156 (7)	0.0005 (5)	0.0002 (5)	0.0021 (5)
C7	0.0258 (9)	0.0357 (10)	0.0203 (8)	−0.0039 (8)	−0.0047 (7)	−0.0057 (7)
C8	0.0219 (8)	0.0409 (11)	0.0166 (8)	0.0064 (8)	−0.0028 (6)	0.0033 (7)
C9	0.0143 (7)	0.0131 (7)	0.0147 (7)	−0.0011 (5)	−0.0029 (5)	0.0007 (5)
C10	0.0173 (7)	0.0141 (7)	0.0251 (8)	0.0014 (6)	0.0020 (6)	0.0008 (6)
C11	0.0189 (8)	0.0210 (8)	0.0332 (9)	0.0038 (6)	0.0048 (7)	−0.0009 (7)
C12	0.0219 (8)	0.0242 (9)	0.0248 (8)	−0.0023 (7)	0.0054 (6)	−0.0063 (7)
C13	0.0213 (8)	0.0198 (8)	0.0197 (7)	−0.0053 (6)	0.0048 (6)	−0.0033 (6)
C14	0.0198 (7)	0.0145 (7)	0.0188 (7)	−0.0022 (6)	0.0014 (6)	0.0013 (6)
C15	0.0168 (7)	0.0103 (7)	0.0133 (6)	−0.0007 (5)	−0.0016 (5)	0.0009 (5)
C16	0.0168 (7)	0.0174 (7)	0.0154 (7)	−0.0020 (6)	−0.0038 (6)	0.0011 (6)
C17	0.0215 (8)	0.0199 (8)	0.0157 (7)	0.0001 (6)	−0.0026 (6)	0.0024 (6)
C18	0.0243 (8)	0.0317 (9)	0.0145 (7)	0.0002 (7)	0.0019 (6)	0.0036 (7)
C19	0.0189 (7)	0.0260 (9)	0.0184 (7)	−0.0035 (6)	0.0019 (6)	0.0031 (7)
C20	0.0155 (7)	0.0194 (8)	0.0159 (7)	−0.0006 (6)	−0.0015 (5)	0.0007 (6)

Geometric parameters (Å, º) top

Se1—P1	2.1241 (5)	C11—C12	1.525 (2)
P1—C1	1.8034 (15)	C11—H11A	0.99
P1—C15	1.8321 (15)	C11—H11B	0.99
P1—C9	1.8354 (15)	C12—C13	1.527 (2)
C2—C3	1.383 (2)	C12—H12A	0.99
C2—C1	1.394 (2)	C12—H12B	0.99
C2—H2	0.95	C13—C14	1.531 (2)
N1—C4	1.376 (2)	C13—H13A	0.99
N1—C8	1.447 (2)	C13—H13B	0.99
N1—C7	1.450 (2)	C14—H14A	0.99
C1—C6	1.401 (2)	C14—H14B	0.99
C3—C4	1.406 (2)	C15—C16	1.535 (2)
C3—H3	0.95	C15—C20	1.536 (2)
C4—C5	1.413 (2)	C15—H15	1
C5—C6	1.383 (2)	C16—C17	1.529 (2)
C5—H5	0.95	C16—H16A	0.99
C6—H6	0.95	C16—H16B	0.99
C7—H7A	0.98	C17—C18	1.524 (2)
C7—H7B	0.98	C17—H17A	0.99
C7—H7C	0.98	C17—H17B	0.99
C8—H8A	0.98	C18—C19	1.524 (2)
C8—H8B	0.98	C18—H18A	0.99
C8—H8C	0.98	C18—H18B	0.99
C9—C10	1.534 (2)	C19—C20	1.531 (2)
C9—C14	1.536 (2)	C19—H19A	0.99
C9—H9	1	C19—H19B	0.99
C10—C11	1.532 (2)	C20—H20A	0.99
C10—H10A	0.99	C20—H20B	0.99
C10—H10B	0.99

C1—P1—C15	107.10 (7)	H11A—C11—H11B	107.9
C1—P1—C9	106.66 (7)	C11—C12—C13	111.49 (13)
C15—P1—C9	107.20 (7)	C11—C12—H12A	109.3
C1—P1—Se1	113.31 (5)	C13—C12—H12A	109.3
C15—P1—Se1	111.45 (5)	C11—C12—H12B	109.3
C9—P1—Se1	110.79 (5)	C13—C12—H12B	109.3
C3—C2—C1	121.75 (15)	H12A—C12—H12B	108
C3—C2—H2	119.1	C12—C13—C14	110.87 (13)
C1—C2—H2	119.1	C12—C13—H13A	109.5
C4—N1—C8	120.06 (15)	C14—C13—H13A	109.5
C4—N1—C7	120.11 (14)	C12—C13—H13B	109.5
C8—N1—C7	117.82 (14)	C14—C13—H13B	109.5
C2—C1—C6	117.66 (13)	H13A—C13—H13B	108.1
C2—C1—P1	120.06 (12)	C13—C14—C9	110.75 (13)
C6—C1—P1	122.26 (11)	C13—C14—H14A	109.5
C2—C3—C4	120.95 (14)	C9—C14—H14A	109.5
C2—C3—H3	119.5	C13—C14—H14B	109.5
C4—C3—H3	119.5	C9—C14—H14B	109.5
N1—C4—C3	121.62 (15)	H14A—C14—H14B	108.1
N1—C4—C5	121.10 (15)	C16—C15—C20	111.07 (12)
C3—C4—C5	117.27 (14)	C16—C15—P1	111.22 (10)
C6—C5—C4	121.14 (15)	C20—C15—P1	110.56 (10)
C6—C5—H5	119.4	C16—C15—H15	107.9
C4—C5—H5	119.4	C20—C15—H15	107.9
C5—C6—C1	121.22 (14)	P1—C15—H15	107.9
C5—C6—H6	119.4	C17—C16—C15	111.31 (12)
C1—C6—H6	119.4	C17—C16—H16A	109.4
N1—C7—H7A	109.5	C15—C16—H16A	109.4
N1—C7—H7B	109.5	C17—C16—H16B	109.4
H7A—C7—H7B	109.5	C15—C16—H16B	109.4
N1—C7—H7C	109.5	H16A—C16—H16B	108
H7A—C7—H7C	109.5	C18—C17—C16	111.28 (13)
H7B—C7—H7C	109.5	C18—C17—H17A	109.4
N1—C8—H8A	109.5	C16—C17—H17A	109.4
N1—C8—H8B	109.5	C18—C17—H17B	109.4
H8A—C8—H8B	109.5	C16—C17—H17B	109.4
N1—C8—H8C	109.5	H17A—C17—H17B	108
H8A—C8—H8C	109.5	C19—C18—C17	110.77 (13)
H8B—C8—H8C	109.5	C19—C18—H18A	109.5
C10—C9—C14	110.55 (12)	C17—C18—H18A	109.5
C10—C9—P1	114.22 (10)	C19—C18—H18B	109.5
C14—C9—P1	110.38 (10)	C17—C18—H18B	109.5
C10—C9—H9	107.1	H18A—C18—H18B	108.1
C14—C9—H9	107.1	C18—C19—C20	110.82 (13)
P1—C9—H9	107.1	C18—C19—H19A	109.5
C11—C10—C9	110.26 (13)	C20—C19—H19A	109.5
C11—C10—H10A	109.6	C18—C19—H19B	109.5
C9—C10—H10A	109.6	C20—C19—H19B	109.5
C11—C10—H10B	109.6	H19A—C19—H19B	108.1
C9—C10—H10B	109.6	C19—C20—C15	111.66 (12)
H10A—C10—H10B	108.1	C19—C20—H20A	109.3
C12—C11—C10	111.95 (14)	C15—C20—H20A	109.3
C12—C11—H11A	109.2	C19—C20—H20B	109.3
C10—C11—H11A	109.2	C15—C20—H20B	109.3
C12—C11—H11B	109.2	H20A—C20—H20B	108
C10—C11—H11B	109.2

C3—C2—C1—C6	0.5 (2)	C15—P1—C9—C14	−179.60 (10)
C3—C2—C1—P1	−177.56 (12)	Se1—P1—C9—C14	58.59 (11)
C15—P1—C1—C2	−147.03 (12)	C14—C9—C10—C11	−56.78 (17)
C9—P1—C1—C2	98.45 (13)	P1—C9—C10—C11	178.02 (11)
Se1—P1—C1—C2	−23.72 (14)	C9—C10—C11—C12	55.47 (18)
C15—P1—C1—C6	34.97 (14)	C10—C11—C12—C13	−54.77 (19)
C9—P1—C1—C6	−79.55 (14)	C11—C12—C13—C14	54.96 (18)
Se1—P1—C1—C6	158.28 (11)	C12—C13—C14—C9	−56.65 (17)
C1—C2—C3—C4	−0.8 (2)	C10—C9—C14—C13	57.86 (16)
C8—N1—C4—C3	−2.9 (2)	P1—C9—C14—C13	−174.79 (10)
C7—N1—C4—C3	−166.45 (16)	C1—P1—C15—C16	−172.11 (10)
C8—N1—C4—C5	177.77 (15)	C9—P1—C15—C16	−57.95 (12)
C7—N1—C4—C5	14.2 (2)	Se1—P1—C15—C16	63.44 (11)
C2—C3—C4—N1	−178.82 (15)	C1—P1—C15—C20	64.01 (11)
C2—C3—C4—C5	0.5 (2)	C9—P1—C15—C20	178.16 (10)
N1—C4—C5—C6	179.44 (15)	Se1—P1—C15—C20	−60.45 (11)
C3—C4—C5—C6	0.1 (2)	C20—C15—C16—C17	−53.87 (17)
C4—C5—C6—C1	−0.4 (2)	P1—C15—C16—C17	−177.46 (11)
C2—C1—C6—C5	0.1 (2)	C15—C16—C17—C18	55.73 (18)
P1—C1—C6—C5	178.14 (11)	C16—C17—C18—C19	−57.24 (18)
C1—P1—C9—C10	60.15 (12)	C17—C18—C19—C20	57.01 (19)
C15—P1—C9—C10	−54.31 (12)	C18—C19—C20—C15	−55.75 (18)
Se1—P1—C9—C10	−176.11 (9)	C16—C15—C20—C19	54.09 (16)
C1—P1—C9—C14	−65.15 (12)	P1—C15—C20—C19	178.06 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Se1ⁱ	1	2.71	3.6546 (15)	157
C19—H19A···Se1ⁱ	0.99	3.04	3.8836 (18)	143

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₃₂NPSe
M_r	396.4
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.3860 (16), 6.8331 (8), 24.113 (3)
β (°)	97.050 (3)
V (Å³)	2025.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.93
Crystal size (mm)	0.29 × 0.12 × 0.05

Data collection
Diffractometer	Bruker APEX DUO 4K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.604, 0.910
No. of measured, independent and observed [I > 2σ(I)] reflections	31168, 5008, 4192
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.063, 1.02
No. of reflections	5008
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −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

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Se1ⁱ	1	2.71	3.6546 (15)	157.1
C19—H19A···Se1ⁱ	0.99	3.04	3.8836 (18)	143.3

Symmetry code: (i) x, y+1, z.

Acknowledgements

Research funds of 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. BrukerAXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bunten, K. A., Chen, L., Fernandez, A. L. & Poë, A. J. (2002). Coord. Chem. Rev. 233–234, 41–51. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Muller, A., Meijboom, R. & Roodt, A. (2006). J. Organomet. Chem. 691, 5794–5801. Web of Science CSD CrossRef CAS Google Scholar
Muller, A., Otto, S. & Roodt, A. (2008). Dalton Trans. pp. 650–657. Web of Science CSD CrossRef PubMed Google Scholar
Otto, S. (2001). Acta Cryst. C57, 793–795. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Roodt, A., Otto, S. & Steyl, G. (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