Dicyclo-hex-yl[4-(dimethyl-amino)-phen-yl]phosphine selenide.

In the title mol-ecule, C(20)H(32)NPSe, the P atom has a distorted tetra-hedral environment resulting in an effective cone angle of 172°. Weak inter-molecular C-H⋯Se inter-actions 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 = 396.4

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.063

S = 1.02

5008 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.53 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/S1600536811054006/nc2259sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811054006/nc2259Isup3.cml

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

C20H32NPSe	F(000) = 832
Mr = 396.4	Dx = 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

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

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(Fo2) + (0.0282P)2 + 1.2459P] where P = (Fo2 + 2Fc2)/3
5008 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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, 1JSe—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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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.

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) .