Tris(4-methyl-phen-yl)phosphine selenide.

In the title mol-ecule, C(21)H(21)PSe or PSe(C(7)H(7))(3), the P atom has a distorted PSeC(3) tetra-hedral environment, formed by the Se atom [P=Se = 2.1119 (5) Å] and three aryl rings. Two short intra-molecular C-H⋯Se contacts occur. In the crystal, weak inter-molecular C-H⋯Se inter-actions link the mol-ecules into zigzag double chains propagating in [100]. The previous report of this structure [Zhdanov et al. (1953 ▶). Dokl. Akad. Nauk SSSR (Russ.) (Proc. Nat. Acad. Sci. USSR), 92, 983-985] contained no geometrical data.

Related literature

For the previous structure determination, see: Zhdanov et al. (1953 ▶). For background to phospho­rus- and selenium-containing ligands, see: Muller et al. (2006 ▶, 2008 ▶); Roodt et al. (2003 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶); For ligand cone angles, see: Tolman (1977 ▶).

Experimental

Crystal data

C21H21PSe

M = 383.31

Monoclinic,

a = 9.8330 (4) Å

b = 19.0584 (9) Å

c = 11.9136 (4) Å

β = 124.969 (2)°

V = 1829.55 (13) Å3

Z = 4

Mo Kα radiation

μ = 2.14 mm−1

T = 100 K

0.36 × 0.14 × 0.13 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.513, T max = 0.769

12931 measured reflections

4555 independent reflections

3748 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.073

S = 1.03

4555 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker 2004 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536810050567/hb5761sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050567/hb5761Isup2.hkl

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

C21H21PSe	F(000) = 784
Mr = 383.31	Dx = 1.392 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3903 reflections
a = 9.8330 (4) Å	θ = 2.5–28.3°
b = 19.0584 (9) Å	µ = 2.14 mm−1
c = 11.9136 (4) Å	T = 100 K
β = 124.969 (2)°	Block, colorless
V = 1829.55 (13) Å3	0.36 × 0.14 × 0.13 mm
Z = 4

Bruker X8 APEXII 4K KappaCCD diffractometer	4555 independent reflections
graphite	3748 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1	Rint = 0.032
ω and φ scans	θmax = 28.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→9
Tmin = 0.513, Tmax = 0.769	k = −25→24
12931 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0326P)2 + 0.6745P] where P = (Fo2 + 2Fc2)/3
4555 reflections	(Δ/σ)max = 0.006
211 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 10 s/frame. A total of 640 frames were collected with a frame width of 0.5° covering up to θ = 28.41° with 99.1% 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	Uiso*/Ueq
Se	0.35082 (2)	0.927791 (11)	0.29390 (2)	0.01903 (7)
P	0.53055 (6)	0.85475 (3)	0.32421 (5)	0.01317 (11)
C1	1.0689 (3)	0.81013 (13)	0.9344 (2)	0.0271 (5)
H1A	1.1148	0.8552	0.9806	0.041*
H1B	1.1584	0.7806	0.9472	0.041*
H1C	1.0164	0.7866	0.9735	0.041*
C2	0.8493 (3)	0.94613 (13)	0.0318 (2)	0.0278 (5)
H2A	0.8035	0.9171	−0.0502	0.042*
H2B	0.9700	0.9400	0.0919	0.042*
H2C	0.8233	0.9955	0.0050	0.042*
C3	0.2520 (3)	0.55993 (11)	0.1189 (2)	0.0255 (5)
H3A	0.2297	0.5513	0.0286	0.038*
H3B	0.1492	0.5544	0.1132	0.038*
H3C	0.3348	0.5263	0.1850	0.038*
C11	0.6948 (2)	0.84178 (10)	0.50352 (18)	0.0138 (4)
C12	0.7425 (2)	0.89697 (11)	0.59514 (19)	0.0172 (4)
H12	0.6909	0.9415	0.5629	0.021*
C13	0.8654 (2)	0.88729 (11)	0.73382 (19)	0.0193 (4)
H13	0.8978	0.9255	0.7953	0.023*
C14	0.9415 (2)	0.82244 (12)	0.78349 (19)	0.0182 (4)
C15	0.8954 (2)	0.76788 (11)	0.6907 (2)	0.0184 (4)
H15	0.9489	0.7237	0.7228	0.022*
C16	0.7729 (2)	0.77686 (11)	0.55230 (19)	0.0169 (4)
H16	0.7421	0.7388	0.4907	0.020*
C21	0.6314 (2)	0.88090 (10)	0.24281 (19)	0.0147 (4)
C22	0.8020 (2)	0.88731 (10)	0.31340 (19)	0.0169 (4)
H22	0.8714	0.8766	0.4084	0.020*
C23	0.8724 (3)	0.90939 (11)	0.2458 (2)	0.0192 (4)
H23	0.9895	0.9143	0.2957	0.023*
C24	0.7742 (3)	0.92422 (10)	0.1068 (2)	0.0181 (4)
C25	0.6036 (3)	0.91762 (12)	0.0366 (2)	0.0245 (5)
H25	0.5346	0.9275	−0.0587	0.029*
C26	0.5322 (3)	0.89686 (12)	0.1030 (2)	0.0246 (5)
H26	0.4149	0.8934	0.0533	0.030*
C31	0.4463 (2)	0.76849 (10)	0.25790 (18)	0.0138 (4)
C32	0.4990 (3)	0.72710 (11)	0.1928 (2)	0.0191 (4)
H32	0.5801	0.7446	0.1806	0.023*
C33	0.4336 (3)	0.66068 (11)	0.1462 (2)	0.0210 (4)
H33	0.4693	0.6334	0.1009	0.025*
C34	0.3169 (2)	0.63330 (11)	0.16437 (19)	0.0177 (4)
C35	0.2645 (3)	0.67488 (11)	0.2292 (2)	0.0203 (4)
H35	0.1842	0.6570	0.2420	0.024*
C36	0.3273 (2)	0.74153 (11)	0.2750 (2)	0.0187 (4)
H36	0.2894	0.7691	0.3183	0.022*

	U11	U22	U33	U12	U13	U23
Se	0.01853 (11)	0.01859 (11)	0.01791 (10)	0.00640 (8)	0.00924 (9)	0.00104 (8)
P	0.0130 (2)	0.0139 (2)	0.0114 (2)	0.00109 (19)	0.0064 (2)	0.00008 (17)
C1	0.0196 (11)	0.0416 (14)	0.0134 (10)	0.0004 (10)	0.0055 (9)	0.0040 (9)
C2	0.0286 (12)	0.0355 (14)	0.0263 (11)	−0.0021 (10)	0.0198 (10)	0.0042 (9)
C3	0.0248 (11)	0.0173 (11)	0.0307 (12)	−0.0015 (9)	0.0137 (10)	−0.0017 (8)
C11	0.0125 (9)	0.0181 (10)	0.0111 (8)	−0.0012 (7)	0.0070 (7)	0.0004 (7)
C12	0.0183 (10)	0.0191 (10)	0.0160 (9)	0.0017 (8)	0.0109 (8)	0.0010 (7)
C13	0.0193 (10)	0.0255 (11)	0.0139 (9)	−0.0025 (9)	0.0100 (9)	−0.0049 (8)
C14	0.0118 (9)	0.0299 (12)	0.0132 (9)	−0.0026 (8)	0.0073 (8)	0.0014 (8)
C15	0.0132 (9)	0.0198 (10)	0.0192 (10)	0.0014 (8)	0.0076 (8)	0.0062 (8)
C16	0.0146 (9)	0.0177 (10)	0.0162 (9)	−0.0003 (8)	0.0076 (8)	−0.0004 (7)
C21	0.0173 (10)	0.0140 (9)	0.0135 (9)	−0.0011 (8)	0.0091 (8)	−0.0005 (7)
C22	0.0177 (10)	0.0171 (10)	0.0142 (9)	0.0002 (8)	0.0082 (8)	0.0002 (7)
C23	0.0151 (10)	0.0212 (11)	0.0208 (10)	−0.0004 (8)	0.0100 (9)	−0.0001 (8)
C24	0.0237 (10)	0.0150 (10)	0.0195 (10)	−0.0008 (8)	0.0147 (9)	0.0002 (7)
C25	0.0232 (11)	0.0330 (13)	0.0143 (9)	−0.0013 (10)	0.0091 (9)	0.0047 (8)
C26	0.0166 (10)	0.0350 (13)	0.0175 (10)	−0.0041 (9)	0.0070 (9)	0.0041 (9)
C31	0.0114 (9)	0.0154 (10)	0.0117 (8)	0.0009 (7)	0.0050 (8)	0.0003 (7)
C32	0.0189 (10)	0.0213 (11)	0.0227 (10)	−0.0017 (8)	0.0152 (9)	−0.0038 (8)
C33	0.0230 (11)	0.0214 (11)	0.0236 (10)	0.0005 (9)	0.0163 (9)	−0.0051 (8)
C34	0.0145 (9)	0.0165 (10)	0.0163 (9)	0.0021 (8)	0.0054 (8)	0.0023 (7)
C35	0.0212 (10)	0.0192 (11)	0.0273 (11)	−0.0004 (9)	0.0179 (10)	0.0022 (8)
C36	0.0213 (11)	0.0198 (10)	0.0216 (10)	0.0013 (8)	0.0161 (9)	0.0001 (8)

Se—P	2.1119 (5)	C15—C16	1.387 (3)
P—C31	1.806 (2)	C15—H15	0.9500
P—C21	1.810 (2)	C16—H16	0.9500
P—C11	1.8106 (19)	C21—C22	1.385 (3)
C1—C14	1.509 (3)	C21—C26	1.398 (3)
C1—H1A	0.9800	C22—C23	1.395 (3)
C1—H1B	0.9800	C22—H22	0.9500
C1—H1C	0.9800	C23—C24	1.386 (3)
C2—C24	1.509 (3)	C23—H23	0.9500
C2—H2A	0.9800	C24—C25	1.386 (3)
C2—H2B	0.9800	C25—C26	1.383 (3)
C2—H2C	0.9800	C25—H25	0.9500
C3—C34	1.503 (3)	C26—H26	0.9500
C3—H3A	0.9800	C31—C36	1.395 (3)
C3—H3B	0.9800	C31—C32	1.397 (3)
C3—H3C	0.9800	C32—C33	1.384 (3)
C11—C12	1.390 (3)	C32—H32	0.9500
C11—C16	1.395 (3)	C33—C34	1.386 (3)
C12—C13	1.391 (3)	C33—H33	0.9500
C12—H12	0.9500	C34—C35	1.394 (3)
C13—C14	1.389 (3)	C35—C36	1.381 (3)
C13—H13	0.9500	C35—H35	0.9500
C14—C15	1.391 (3)	C36—H36	0.9500
C31—P—C21	105.74 (9)	C15—C16—C11	120.03 (18)
C31—P—C11	105.50 (9)	C15—C16—H16	120.0
C21—P—C11	106.11 (9)	C11—C16—H16	120.0
C31—P—Se	113.32 (6)	C22—C21—C26	118.64 (18)
C21—P—Se	112.88 (7)	C22—C21—P	122.94 (14)
C11—P—Se	112.64 (7)	C26—C21—P	118.40 (15)
C14—C1—H1A	109.5	C21—C22—C23	120.34 (18)
C14—C1—H1B	109.5	C21—C22—H22	119.8
H1A—C1—H1B	109.5	C23—C22—H22	119.8
C14—C1—H1C	109.5	C24—C23—C22	120.98 (19)
H1A—C1—H1C	109.5	C24—C23—H23	119.5
H1B—C1—H1C	109.5	C22—C23—H23	119.5
C24—C2—H2A	109.5	C25—C24—C23	118.43 (19)
C24—C2—H2B	109.5	C25—C24—C2	120.15 (18)
H2A—C2—H2B	109.5	C23—C24—C2	121.41 (19)
C24—C2—H2C	109.5	C26—C25—C24	121.11 (19)
H2A—C2—H2C	109.5	C26—C25—H25	119.4
H2B—C2—H2C	109.5	C24—C25—H25	119.4
C34—C3—H3A	109.5	C25—C26—C21	120.48 (19)
C34—C3—H3B	109.5	C25—C26—H26	119.8
H3A—C3—H3B	109.5	C21—C26—H26	119.8
C34—C3—H3C	109.5	C36—C31—C32	118.80 (18)
H3A—C3—H3C	109.5	C36—C31—P	118.96 (15)
H3B—C3—H3C	109.5	C32—C31—P	122.22 (15)
C12—C11—C16	119.12 (17)	C33—C32—C31	120.29 (19)
C12—C11—P	119.65 (15)	C33—C32—H32	119.9
C16—C11—P	121.22 (14)	C31—C32—H32	119.9
C11—C12—C13	120.32 (19)	C32—C33—C34	121.15 (19)
C11—C12—H12	119.8	C32—C33—H33	119.4
C13—C12—H12	119.8	C34—C33—H33	119.4
C14—C13—C12	120.87 (19)	C33—C34—C35	118.29 (19)
C14—C13—H13	119.6	C33—C34—C3	120.78 (19)
C12—C13—H13	119.6	C35—C34—C3	120.90 (19)
C13—C14—C15	118.43 (18)	C36—C35—C34	121.24 (19)
C13—C14—C1	121.52 (19)	C36—C35—H35	119.4
C15—C14—C1	120.0 (2)	C34—C35—H35	119.4
C16—C15—C14	121.20 (19)	C35—C36—C31	120.22 (19)
C16—C15—H15	119.4	C35—C36—H36	119.9
C14—C15—H15	119.4	C31—C36—H36	119.9
C31—P—C11—C12	−155.80 (16)	C21—C22—C23—C24	−1.1 (3)
C21—P—C11—C12	92.29 (17)	C22—C23—C24—C25	1.0 (3)
Se—P—C11—C12	−31.70 (17)	C22—C23—C24—C2	−178.22 (19)
C31—P—C11—C16	23.05 (18)	C23—C24—C25—C26	0.1 (3)
C21—P—C11—C16	−88.86 (17)	C2—C24—C25—C26	179.3 (2)
Se—P—C11—C16	147.15 (14)	C24—C25—C26—C21	−1.0 (4)
C16—C11—C12—C13	−0.6 (3)	C22—C21—C26—C25	0.9 (3)
P—C11—C12—C13	178.27 (15)	P—C21—C26—C25	179.49 (18)
C11—C12—C13—C14	−0.6 (3)	C21—P—C31—C36	−164.39 (15)
C12—C13—C14—C15	1.9 (3)	C11—P—C31—C36	83.44 (16)
C12—C13—C14—C1	−176.97 (19)	Se—P—C31—C36	−40.24 (16)
C13—C14—C15—C16	−2.0 (3)	C21—P—C31—C32	17.16 (19)
C1—C14—C15—C16	176.88 (18)	C11—P—C31—C32	−95.02 (17)
C14—C15—C16—C11	0.8 (3)	Se—P—C31—C32	141.31 (15)
C12—C11—C16—C15	0.5 (3)	C36—C31—C32—C33	0.1 (3)
P—C11—C16—C15	−178.35 (15)	P—C31—C32—C33	178.60 (16)
C31—P—C21—C22	−111.10 (18)	C31—C32—C33—C34	−0.9 (3)
C11—P—C21—C22	0.6 (2)	C32—C33—C34—C35	1.0 (3)
Se—P—C21—C22	124.48 (16)	C32—C33—C34—C3	−177.32 (19)
C31—P—C21—C26	70.41 (18)	C33—C34—C35—C36	−0.3 (3)
C11—P—C21—C26	−177.85 (17)	C3—C34—C35—C36	178.00 (19)
Se—P—C21—C26	−54.02 (18)	C34—C35—C36—C31	−0.4 (3)
C26—C21—C22—C23	0.1 (3)	C32—C31—C36—C35	0.5 (3)
P—C21—C22—C23	−178.38 (15)	P—C31—C36—C35	−177.98 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Se	0.95	3.04	3.495 (2)	111
C12—H12···Sei	0.95	3.18	3.890 (2)	133
C2—H2B···Seii	0.98	3.09	4.067 (2)	176
C36—H36···Se	0.95	3.13	3.556 (2)	109

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Se	0.95	3.04	3.495 (2)	111
C12—H12⋯Sei	0.95	3.18	3.890 (2)	133
C2—H2B⋯Seii	0.98	3.09	4.067 (2)	176
C36—H36⋯Se	0.95	3.13	3.556 (2)	109

Symmetry codes: (i) ; (ii) .