Bis(2,4-dimeth­oxy­phen­yl)(phen­yl)phosphine selenide

Muller, A.

doi:10.1107/S1600536810049366

organic compounds

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Volume 67| Part 1| January 2011| Page o97

https://doi.org/10.1107/S1600536810049366

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Bis(2,4-dimethoxyphenyl)(phenyl)phosphine selenide

Alfred Muller ^a ^*

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

(Received 24 November 2010; accepted 25 November 2010; online 11 December 2010)

In the title molecule, C₂₂H₂₃O₄PSe, the P atom has a distorted tetrahedral environment formed by the selenide atom [P=Se = 2.1219 (5) Å] and three aryl rings. The orientations of the methoxy groups in the two 2,4-dimethoxyphenyl 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 intermolecular C—H⋯Se interactions link the molecules 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_r = 461.33
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.078
S = 1.04
5151 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 1.41 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810049366/cv5007sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810049366/cv5007Isup2.hkl

checkCIF report

Comment top

There has been extensive development in understanding the transition metal phosphorous bond by various groups, including our own, with various techniques such as single-crystal X-ray crystallography, multi nuclear NMR and IR (Roodt et al., 2003). As part of this systematic investigation we are now also studying selenium bonded 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 J(³¹P-⁷⁷Se) coupling can also be used as an additional probe to obtain more information regarding the nature of the phosphorous bond. Reported here is the first single-crystal structure of the compound PPh(2,4-OMe-C₆H₃)₂ to date (Cambridge Structural Database; Version 5.31, update of August; Allen, 2002).

Crystals of the title compound, (I), packs in the P2₁/c (Z=4) space group with the molecules lying on general positions. All geometrical features of the molecule (Allen, 2002) are as expected with the selenium atom and the three aryl groups adopting a distorted arrangement about phosphorous (see Fig. 1 and Table 1). The cone angle was found to be 176.9° when the Se—P distance is adjusted to 2.28 Å (the default value used in Tolman, 1977) Two different orientations for the methoxy moieties are noted and is probably due to some weak interactions (Table 1) forcing it into the conformations observed.

Related literature top

For background to studies aimed at understanding the transition metal–phosphorous bond, see: Muller et al. (2006,2008); Roodt et al. (2003) Tolman (1977). For the synthesis of ortho-substituted arylalkylphosphanes, see: Riihimäki et al. (2003). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

PPh(2,4-OMe-C₆H₃)₂ were prepared either by direct ortho metallation of anisole with BuLi followed the addition of the appropriate chlorophosphine or by metal/halogen exchange between BuLi and 1-bromo-2,4-dimethoxybenzene followed by the addition of PPhCl₂ according to established methods (Riihimäki et al. 2003).

Eqimolar amounts of KSeCN and the PPh(2,4-OMe-C₆H₃)₂ compound (ca 0.04 mmol) were dissolved in the minimum amounts of methanol (10 – 20 ml). The KSeCN solution was added dropwise (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.

Analytical data: ³¹P {H} NMR (CDCl₃, 121.42 MHz): For PPh(2,4-OMe-C₆H₃)₂ δ = -36.54 (s) For SePPh(2,4-OMe-C₆H₃)₂ δ = 20.45 (t, ¹J_P—Se = 717.5 Hz)

Structure description top

Computing details top

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).

Figures top

Fig. 1. View of (I) (50% probability displacement ellipsoids). H atoms have been omitted for clarity. For the C atoms, the first digit indicates the ring number and the second digit indicates the position of the atom in the ring.

Bis(2,4-dimethoxyphenyl)(phenyl)phosphine selenide top

Crystal data top

C₂₂H₂₃O₄PSe	F(000) = 944
M_r = 461.33	D_x = 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

Data collection top

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

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0398P)² + 1.21P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.078	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 1.41 e Å⁻³
5151 reflections	Δρ_min = −0.20 e Å⁻³
257 parameters

Crystal data top

C₂₂H₂₃O₄PSe	V = 2071.6 (4) Å³
M_r = 461.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3840 (13) Å	µ = 1.92 mm⁻¹
b = 13.3023 (14) Å	T = 150 K
c = 16.667 (2) Å	0.34 × 0.28 × 0.06 mm
β = 95.311 (4)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	5151 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4413 reflections with I > 2σ(I)
T_min = 0.566, T_max = 0.891	R_int = 0.030
24588 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.04	Δρ_max = 1.41 e Å⁻³
5151 reflections	Δρ_min = −0.20 e Å⁻³
257 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₃O₄PSe
M_r	461.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	9.3840 (13), 13.3023 (14), 16.667 (2)
β (°)	95.311 (4)
V (Å³)	2071.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.92
Crystal size (mm)	0.34 × 0.28 × 0.06

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.566, 0.891
No. of measured, independent and observed [I > 2σ(I)] reflections	24588, 5151, 4413
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.078, 1.04
No. of reflections	5151
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.41, −0.20

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), 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
C3—H3C···Seⁱ	0.98	2.94	3.8774 (19)	159.9

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

The University of the Free State (Professor A. Roodt) is thanked for the use of its diffractometer.

References

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