Bis(2,4-dimeth-oxy-phen-yl)(phen-yl)phosphine selenide.

In the title mol-ecule, C(22)H(23)O(4)PSe, the P atom has a distorted tetra-hedral environment formed by the selenide atom [P=Se = 2.1219 (5) Å] and three aryl rings. The orientations of the meth-oxy groups in the two 2,4-dimeth-oxy-phenyl ligands are distinct, as seen from the torsion angles: C-C-O-C = 14.7 (3) and 175.97 (17)° in one ligand, and -9.1 (2) and 5.1 (3)° in the other. In the crystal, weak inter-molecular C-H⋯Se inter-actions link the mol-ecules into zigzag chains propagated in [010].

Related literature

For background to studies aimed at understanding the trans­ition metal–phosphorus bond, see: Muller et al. (2006 ▶); Roodt et al. (2003 ▶) Tolman (1977 ▶). As part of this systematic investigation we are now also studying selenium-bonded phosphorus ligands, see: Muller et al. (2008 ▶). For the synthesis of ortho-substituted aryl­alkyl­phosphanes, see: Riihimäki et al. (2003 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C22H23O4PSe

M = 461.33

Monoclinic,

a = 9.3840 (13) Å

b = 13.3023 (14) Å

c = 16.667 (2) Å

β = 95.311 (4)°

V = 2071.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.92 mm−1

T = 150 K

0.34 × 0.28 × 0.06 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.566, T max = 0.891

24588 measured reflections

5151 independent reflections

4413 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.078

S = 1.04

5151 reflections

257 parameters

H-atom parameters constrained

Δρmax = 1.41 e Å−3

Δρmin = −0.20 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/S1600536810049366/cv5007sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049366/cv5007Isup2.hkl

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

C22H23O4PSe	F(000) = 944
Mr = 461.33	Dx = 1.479 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5013 reflections
a = 9.3840 (13) Å	θ = 2.7–28.3°
b = 13.3023 (14) Å	µ = 1.92 mm−1
c = 16.667 (2) Å	T = 150 K
β = 95.311 (4)°	Plate, colourless
V = 2071.6 (4) Å3	0.34 × 0.28 × 0.06 mm
Z = 4

Bruker X8 APEXII 4K Kappa CCD diffractometer	5151 independent reflections
graphite	4413 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1	Rint = 0.030
ω & φ scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.566, Tmax = 0.891	k = −17→16
24588 measured reflections	l = −22→22

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.0398P)2 + 1.21P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 1.41 e Å−3
5151 reflections	Δρmin = −0.20 e Å−3
257 parameters

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 1125 frames were collected with a frame width of 0.5° covering up to θ = 28.25° with 99.7% 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.

	x	y	z	Uiso*/Ueq
Se	0.31675 (2)	0.914803 (13)	0.136815 (10)	0.02690 (7)
P	0.33832 (5)	0.78342 (3)	0.06676 (2)	0.01886 (10)
C11	0.22855 (19)	0.79244 (13)	−0.02854 (9)	0.0193 (3)
C12	0.24045 (19)	0.72308 (12)	−0.09174 (10)	0.0207 (3)
C13	0.1607 (2)	0.73473 (14)	−0.16557 (10)	0.0234 (4)
H13	0.1699	0.6879	−0.2078	0.028*
C14	0.06675 (19)	0.81588 (14)	−0.17707 (10)	0.0229 (3)
C15	0.05290 (19)	0.88571 (14)	−0.11587 (11)	0.0234 (3)
H15	−0.0107	0.9411	−0.1241	0.028*
C16	0.13423 (19)	0.87254 (13)	−0.04265 (10)	0.0221 (3)
H16	0.1251	0.9199	−0.0007	0.027*
C1	0.3774 (3)	0.58741 (14)	−0.13985 (12)	0.0330 (5)
H1A	0.2998	0.5417	−0.1591	0.049*
H1B	0.4627	0.5483	−0.1213	0.049*
H1C	0.3996	0.632	−0.1838	0.049*
O1	0.33407 (15)	0.64596 (9)	−0.07480 (7)	0.0271 (3)
C2	−0.1108 (2)	0.89791 (18)	−0.26447 (13)	0.0367 (5)
H2A	−0.1793	0.8935	−0.2237	0.055*
H2B	−0.1616	0.89	−0.3182	0.055*
H2C	−0.0633	0.9636	−0.2607	0.055*
O2	−0.00636 (14)	0.82027 (11)	−0.25114 (8)	0.0297 (3)
C21	0.28849 (19)	0.66839 (13)	0.11441 (10)	0.0206 (3)
C22	0.35987 (19)	0.63756 (13)	0.18822 (10)	0.0210 (3)
C23	0.3213 (2)	0.54914 (13)	0.22579 (10)	0.0229 (3)
H23	0.371	0.5286	0.2753	0.028*
C24	0.2101 (2)	0.49165 (13)	0.19012 (11)	0.0254 (4)
C25	0.1364 (2)	0.52101 (14)	0.11711 (11)	0.0265 (4)
H25	0.0601	0.4812	0.0929	0.032*
C26	0.1761 (2)	0.60867 (14)	0.08048 (10)	0.0241 (4)
H26	0.1257	0.6288	0.031	0.029*
C3	0.5321 (2)	0.67676 (15)	0.29847 (11)	0.0275 (4)
H3A	0.4586	0.6798	0.3365	0.041*
H3B	0.6066	0.7267	0.3136	0.041*
H3C	0.5748	0.6095	0.2998	0.041*
O3	0.46854 (14)	0.69765 (10)	0.21903 (7)	0.0273 (3)
C4	0.2265 (3)	0.37696 (16)	0.30097 (12)	0.0376 (5)
H4A	0.3269	0.3586	0.2978	0.056*
H4B	0.1746	0.3194	0.3206	0.056*
H4C	0.2209	0.4336	0.3381	0.056*
O4	0.16333 (17)	0.40516 (10)	0.22236 (9)	0.0352 (3)
C31	0.52039 (19)	0.76605 (13)	0.04006 (10)	0.0206 (3)
C32	0.5942 (2)	0.84791 (14)	0.01235 (11)	0.0258 (4)
H32	0.5517	0.9128	0.011	0.031*
C33	0.7297 (2)	0.83512 (16)	−0.01327 (12)	0.0315 (4)
H33	0.7795	0.8912	−0.0323	0.038*
C35	0.7206 (2)	0.65944 (16)	0.01708 (12)	0.0321 (4)
H35	0.7641	0.5949	0.0192	0.039*
C36	0.5850 (2)	0.67188 (14)	0.04235 (11)	0.0276 (4)
H36	0.5358	0.6156	0.0614	0.033*
C34	0.7925 (2)	0.74100 (17)	−0.01121 (12)	0.0336 (4)
H343	0.8849	0.7324	−0.0292	0.04*

	U11	U22	U33	U12	U13	U23
Se	0.04157 (12)	0.02049 (10)	0.01806 (10)	0.00414 (7)	−0.00027 (7)	−0.00378 (6)
P	0.0259 (2)	0.0170 (2)	0.01349 (19)	0.00107 (16)	0.00077 (16)	0.00097 (15)
C11	0.0237 (8)	0.0208 (8)	0.0134 (7)	−0.0003 (6)	0.0014 (6)	0.0018 (6)
C12	0.0262 (9)	0.0186 (8)	0.0174 (8)	−0.0006 (6)	0.0025 (6)	0.0025 (6)
C13	0.0297 (9)	0.0244 (9)	0.0158 (7)	−0.0029 (7)	0.0005 (7)	0.0001 (6)
C14	0.0217 (8)	0.0286 (9)	0.0180 (8)	−0.0046 (7)	−0.0011 (6)	0.0050 (7)
C15	0.0213 (8)	0.0263 (9)	0.0227 (8)	0.0026 (7)	0.0020 (7)	0.0049 (7)
C16	0.0248 (9)	0.0235 (9)	0.0184 (8)	0.0007 (7)	0.0039 (6)	0.0006 (6)
C1	0.0545 (13)	0.0214 (9)	0.0234 (9)	0.0075 (8)	0.0059 (9)	−0.0047 (7)
O1	0.0419 (8)	0.0225 (6)	0.0164 (6)	0.0092 (6)	0.0000 (5)	−0.0015 (5)
C2	0.0274 (10)	0.0493 (13)	0.0317 (10)	0.0067 (9)	−0.0061 (8)	0.0054 (9)
O2	0.0304 (7)	0.0358 (7)	0.0214 (6)	0.0008 (6)	−0.0065 (5)	0.0035 (6)
C21	0.0286 (9)	0.0181 (8)	0.0155 (7)	0.0013 (7)	0.0039 (6)	0.0019 (6)
C22	0.0247 (9)	0.0206 (8)	0.0179 (8)	0.0020 (7)	0.0041 (6)	0.0008 (6)
C23	0.0299 (9)	0.0210 (8)	0.0182 (8)	0.0028 (7)	0.0039 (7)	0.0043 (6)
C24	0.0340 (10)	0.0195 (8)	0.0234 (8)	0.0001 (7)	0.0064 (7)	0.0022 (7)
C25	0.0333 (10)	0.0251 (9)	0.0212 (8)	−0.0053 (7)	0.0027 (7)	−0.0013 (7)
C26	0.0309 (9)	0.0234 (9)	0.0179 (8)	0.0012 (7)	0.0019 (7)	0.0004 (6)
C3	0.0284 (9)	0.0308 (10)	0.0221 (8)	0.0028 (8)	−0.0045 (7)	0.0052 (7)
O3	0.0330 (7)	0.0272 (7)	0.0205 (6)	−0.0056 (5)	−0.0038 (5)	0.0062 (5)
C4	0.0573 (14)	0.0247 (10)	0.0301 (10)	−0.0049 (9)	−0.0003 (9)	0.0107 (8)
O4	0.0496 (9)	0.0254 (7)	0.0299 (7)	−0.0115 (6)	−0.0010 (6)	0.0090 (5)
C31	0.0246 (8)	0.0217 (8)	0.0152 (7)	0.0004 (6)	0.0000 (6)	0.0013 (6)
C32	0.0313 (10)	0.0216 (9)	0.0241 (9)	−0.0002 (7)	0.0003 (7)	0.0035 (7)
C33	0.0316 (10)	0.0324 (10)	0.0303 (10)	−0.0052 (8)	0.0028 (8)	0.0055 (8)
C35	0.0351 (11)	0.0305 (10)	0.0313 (10)	0.0093 (8)	0.0060 (8)	0.0051 (8)
C36	0.0335 (10)	0.0238 (9)	0.0260 (9)	0.0034 (7)	0.0059 (7)	0.0068 (7)
C34	0.0282 (10)	0.0425 (12)	0.0308 (10)	0.0039 (9)	0.0065 (8)	0.0052 (9)

Se—P	2.1219 (5)	C23—C24	1.383 (3)
P—C21	1.8054 (17)	C23—H23	0.95
P—C11	1.8154 (17)	C24—O4	1.359 (2)
P—C31	1.8196 (18)	C24—C25	1.398 (3)
C11—C16	1.391 (2)	C25—C26	1.383 (3)
C11—C12	1.412 (2)	C25—H25	0.95
C12—O1	1.363 (2)	C26—H26	0.95
C12—C13	1.389 (2)	C3—O3	1.428 (2)
C13—C14	1.395 (3)	C3—H3A	0.98
C13—H13	0.95	C3—H3B	0.98
C14—O2	1.357 (2)	C3—H3C	0.98
C14—C15	1.395 (3)	C4—O4	1.437 (2)
C15—C16	1.389 (2)	C4—H4A	0.98
C15—H15	0.95	C4—H4B	0.98
C16—H16	0.95	C4—H4C	0.98
C1—O1	1.425 (2)	C31—C36	1.391 (3)
C1—H1A	0.98	C31—C32	1.392 (2)
C1—H1B	0.98	C32—C33	1.389 (3)
C1—H1C	0.98	C32—H32	0.95
C2—O2	1.427 (2)	C33—C34	1.383 (3)
C2—H2A	0.98	C33—H33	0.95
C2—H2B	0.98	C35—C34	1.383 (3)
C2—H2C	0.98	C35—C36	1.387 (3)
C21—C26	1.397 (3)	C35—H35	0.95
C21—C22	1.406 (2)	C36—H36	0.95
C22—O3	1.359 (2)	C34—H343	0.95
C22—C23	1.396 (2)
C21—P—C11	106.96 (8)	C24—C23—C22	119.33 (16)
C21—P—C31	106.69 (8)	C24—C23—H23	120.3
C11—P—C31	105.31 (8)	C22—C23—H23	120.3
C21—P—Se	114.47 (6)	O4—C24—C23	123.80 (17)
C11—P—Se	110.59 (6)	O4—C24—C25	115.40 (17)
C31—P—Se	112.25 (6)	C23—C24—C25	120.80 (16)
C16—C11—C12	117.86 (15)	C26—C25—C24	119.22 (17)
C16—C11—P	119.94 (13)	C26—C25—H25	120.4
C12—C11—P	122.12 (13)	C24—C25—H25	120.4
O1—C12—C13	123.50 (15)	C25—C26—C21	121.63 (16)
O1—C12—C11	115.53 (15)	C25—C26—H26	119.2
C13—C12—C11	120.97 (16)	C21—C26—H26	119.2
C12—C13—C14	119.33 (16)	O3—C3—H3A	109.5
C12—C13—H13	120.3	O3—C3—H3B	109.5
C14—C13—H13	120.3	H3A—C3—H3B	109.5
O2—C14—C15	124.28 (17)	O3—C3—H3C	109.5
O2—C14—C13	114.71 (16)	H3A—C3—H3C	109.5
C15—C14—C13	121.01 (16)	H3B—C3—H3C	109.5
C16—C15—C14	118.54 (17)	C22—O3—C3	118.07 (14)
C16—C15—H15	120.7	O4—C4—H4A	109.5
C14—C15—H15	120.7	O4—C4—H4B	109.5
C15—C16—C11	122.29 (16)	H4A—C4—H4B	109.5
C15—C16—H16	118.9	O4—C4—H4C	109.5
C11—C16—H16	118.9	H4A—C4—H4C	109.5
O1—C1—H1A	109.5	H4B—C4—H4C	109.5
O1—C1—H1B	109.5	C24—O4—C4	117.42 (16)
H1A—C1—H1B	109.5	C36—C31—C32	118.98 (17)
O1—C1—H1C	109.5	C36—C31—P	121.64 (14)
H1A—C1—H1C	109.5	C32—C31—P	119.29 (14)
H1B—C1—H1C	109.5	C33—C32—C31	120.27 (18)
C12—O1—C1	118.54 (14)	C33—C32—H32	119.9
O2—C2—H2A	109.5	C31—C32—H32	119.9
O2—C2—H2B	109.5	C34—C33—C32	120.24 (18)
H2A—C2—H2B	109.5	C34—C33—H33	119.9
O2—C2—H2C	109.5	C32—C33—H33	119.9
H2A—C2—H2C	109.5	C34—C35—C36	120.01 (19)
H2B—C2—H2C	109.5	C34—C35—H35	120
C14—O2—C2	117.07 (15)	C36—C35—H35	120
C26—C21—C22	117.95 (15)	C35—C36—C31	120.61 (18)
C26—C21—P	121.36 (13)	C35—C36—H36	119.7
C22—C21—P	120.67 (14)	C31—C36—H36	119.7
O3—C22—C23	122.88 (15)	C33—C34—C35	119.89 (19)
O3—C22—C21	116.05 (15)	C33—C34—H343	120.1
C23—C22—C21	121.05 (16)	C35—C34—H343	120.1
C21—P—C11—C16	118.16 (14)	P—C21—C22—O3	−1.7 (2)
C31—P—C11—C16	−128.58 (14)	C26—C21—C22—C23	1.1 (3)
Se—P—C11—C16	−7.10 (16)	P—C21—C22—C23	179.51 (13)
C21—P—C11—C12	−65.25 (16)	O3—C22—C23—C24	−179.45 (16)
C31—P—C11—C12	48.01 (16)	C21—C22—C23—C24	−0.7 (3)
Se—P—C11—C12	169.49 (13)	C22—C23—C24—O4	−179.15 (17)
C16—C11—C12—O1	−179.90 (15)	C22—C23—C24—C25	0.1 (3)
P—C11—C12—O1	3.4 (2)	O4—C24—C25—C26	179.37 (17)
C16—C11—C12—C13	0.1 (3)	C23—C24—C25—C26	0.0 (3)
P—C11—C12—C13	−176.53 (14)	C24—C25—C26—C21	0.4 (3)
O1—C12—C13—C14	179.58 (16)	C22—C21—C26—C25	−0.9 (3)
C11—C12—C13—C14	−0.4 (3)	P—C21—C26—C25	−179.33 (14)
C12—C13—C14—O2	−179.81 (16)	C23—C22—O3—C3	−9.1 (2)
C12—C13—C14—C15	0.6 (3)	C21—C22—O3—C3	172.14 (16)
O2—C14—C15—C16	−179.96 (16)	C23—C24—O4—C4	5.1 (3)
C13—C14—C15—C16	−0.4 (3)	C25—C24—O4—C4	−174.23 (18)
C14—C15—C16—C11	0.1 (3)	C21—P—C31—C36	12.52 (17)
C12—C11—C16—C15	0.1 (3)	C11—P—C31—C36	−100.93 (16)
P—C11—C16—C15	176.81 (14)	Se—P—C31—C36	138.67 (14)
C13—C12—O1—C1	14.7 (3)	C21—P—C31—C32	−171.12 (14)
C11—C12—O1—C1	−165.27 (17)	C11—P—C31—C32	75.43 (15)
C15—C14—O2—C2	−4.4 (3)	Se—P—C31—C32	−44.96 (15)
C13—C14—O2—C2	175.97 (17)	C36—C31—C32—C33	0.6 (3)
C11—P—C21—C26	−4.58 (17)	P—C31—C32—C33	−175.85 (14)
C31—P—C21—C26	−116.89 (15)	C31—C32—C33—C34	−0.2 (3)
Se—P—C21—C26	118.29 (14)	C34—C35—C36—C31	−0.4 (3)
C11—P—C21—C22	177.05 (14)	C32—C31—C36—C35	−0.3 (3)
C31—P—C21—C22	64.74 (16)	P—C31—C36—C35	176.06 (15)
Se—P—C21—C22	−60.07 (16)	C32—C33—C34—C35	−0.5 (3)
C26—C21—C22—O3	179.91 (15)	C36—C35—C34—C33	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3C···Sei	0.98	2.94	3.8774 (19)	160.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3C⋯Sei	0.98	2.94	3.8774 (19)	160

Symmetry code: (i) .