Bis[2-(morpholinometh­yl)phen­yl]phenyl­phosphane

doi:10.1107/S1600536809048946

Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3158–o3159.

Published online 2009 November 21. doi: 10.1107/S1600536809048946

PMCID: PMC2971958

Bis[2-(morpholinomethyl)phenyl]phenylphosphane

Ancuta Covaci,^a Richard A. Varga,^a^* and Cristian Silvestru^a

^aFaculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Arany Janos Str. no. 11, RO-400028, Cluj Napoca, Romania

Correspondence e-mail: richy/at/chem.ubbcluj.ro

Received November 11, 2009; Accepted November 17, 2009.

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Abstract

The title compound, C₂₈H₃₃N₂O₂P, contains a pentacoordinated P atom as a result of the weak N→P intramolecular interactions, with three C atoms, two N atoms and the lone pair arranged in a dicapped pseudo-tetrahedral geometry. The morpholine rings exhibit an almost ideal chair conformation. In the crystal, two weak C—H (...)

O hydrogen-bond interactions link the molecules in layers stacked along the a axis; there are no further interactions between the layers.

Related literature

For related structures, see Chuit et al. (1993

); Copolovici, et al. (2007

); Copolovici, Silvestru, Isaia et al. (2008

); Copolovici, Silvestru & Varga (2008

). For the use of phosphines containing organic groups with pendant arms as ligands in the coordination chemistry, see Alonso et al. (2003

), Brammer et al. (2000

), de Graaf et al. (1988

), Kapteijn et al. (1996

), Fierro-Arias et al. (2005

), Pfeiffer et al. (2000

)]. For van der Waals radii, see: Emsley (1994

An external file that holds a picture, illustration, etc.
Object name is e-65-o3158-scheme1.jpg Object name is e-65-o3158-scheme1.jpg

Experimental

Crystal data

C₂₈H₃₃N₂O₂P
M _r = 460.53
Monoclinic,
a = 14.640 (7) Å
b = 11.656 (5) Å
c = 14.998 (7) Å
β = 101.950 (9)°
V = 2504 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 297 K
0.30 × 0.26 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T _min = 0.960, T _max = 0.984
17694 measured reflections
4412 independent reflections
3184 reflections with I > 2σ(I)
R _int = 0.099

Refinement

R[F ² > 2σ(F ²)] = 0.112
wR(F ²) = 0.207
S = 1.23
4412 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: SMART (Bruker, 2000

); cell refinement: SAINT-Plus (Bruker, 2001

); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008

); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008

); molecular graphics: DIAMOND 3 (Brandenburg & Putz, 2006

) and ORTEP-3 (Farrugia, 1997

); software used to prepare material for publication: publCIF (Westrip, 2009

Table 1

Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048946/bq2178sup1.cif

Click here to view.^{(24K, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048946/bq2178Isup2.hkl

Click here to view.^{(216K, hkl)}

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

Acknowledgments

We thank the National Center for X-ray Diffraction, Cluj-Napoca, Romania, for support of the solid-state structure determinations.

supplementary crystallographic information

Comment

Phosphines containing organic groups with pendant arms, e.g. PPh_n[C₆H₄(CH₂NMe₂)-2]_3-n, were successfully used as ligands in the coordination chemistry of various transition metals [Co (Brammer et al., 2000), Rh (Alonso et al., 2003), Pd (de Graaf et al., 1988; Kapteijn et al., 1996; Fierro-Arias et al., 2005), Pt (Pfeiffer et al., 2000)]. In order to extend this class of potential phosphine ligands we decided to investigate other related compounds and here we report on the molecular structure of PPh[C₆H₄{CH₂N(CH₂CH₂)₂O}-2]₂.

The structure of (I) with its atomic numbering scheme is depicted in Figure 1. The N atoms from the two morphilinyl pendant arms form weak intramolecular interactions with the central phosphorus atom [N1···P1 = 3.038 (4) and N2···P1 = 3.105 (4) Å; c.f. sums of the covalent radii, Σr_cov(P,N) 1.80 Å, and van der Waals radii, Σr_vdW(P,N) 3.44 Å (Emsley, 1994)]. The magnitude of the N→P interactions is similar to the ones present in tris[2-(dimethylaminomethyl)phenyl]phosphane (Chuit et al., 1993). Taking into account these intramolecular interactions a dicapped pseudo-tetrahedron can be considered around the phosphorus, with the three carbon atoms and the phosphorus lone pair describing the tetrahedral skeleton.

An almost ideal chair conformation was observed for both morpholinyl groups with torsion angles [C8—N1—C11—C10 = 56.5 (6)°, C10—O1—C9—C8 = -57.9 (6)°, C19—N2—C21—C22 = 56.7 (6)° and C22—O2—C20—C19 = -58.1 (6)°] similar with those found in 4-benzylmorpholin-4-ium chloride (Copolovici et al., 2007), tris[2-(morpholin-4-ylmethyl)phenyl-κ²C¹,N]antimony(III) (Copolovici, Silvestru & Varga (2008) and in di-µ-chlorido-bis{[2-(morpholin-4-ylmethyl)phenyl-k²C¹,N]palladium(II)} (Copolovici, Silvestru, Isaia et al. (2008).

Weak hydrogen bonds between one morpholinyl oxygen atom and an aromatic C—H [H25···O1ⁱ = 2.46 Å; symmetry code: (i) x, -y + 1/2, z - 1/2] and between the other morpholinyl oxygen and a CH₂ hydrogen [H11B···O2ⁱⁱ = 2.55 Å; symmetry code: (ii) x, y - 1, z] (Figure 2) give rise to a bidimensional layer along the bc plane. The layers are stacked along the a axis, with no further interactions (Figure 3).

Experimental

To a solution of the [2-{O(CH₂CH₂)₂NCH₂}C₆H₄]Li (2.72 g, 14 mmol) in cold thf (-70 °C) was added dropwise a solution of PPhCl₂(1.01 ml, ρ = 1.319 g/ml, 7 mmol) in thf. The reaction mixture was stirred at -70 °C for additional 2 h, then it was allowed to reach the room temperature and the solvent was removed under vacuum. The obtained oily product was extracted with CH₂Cl₂. The solid residue was filtered off and the solvent was removed in vacuum. The remaining viscous oil solidified on addition of hexane. The title compound was isolated as a white solid. Colorless crystals suitable for X-ray diffraction studies were obtained by slow diffusion of hexane into a CH₂Cl₂ solution of the title compound (1:1 v/v ratio) (yield: 2.76 g, 81%; m.p. 89 °C).

Figures

Fig. 1.

: The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Fig. 2.

: Hydrogen bonds in the title compound (dashed lines; only H atoms involved in interactions are shown). Symmetry codes: (i) x, -y+1/2, z-1/2; (ii) x, y-1, z.

Fig. 3.

: Molecular packing as viewed along the c axis. Hydrogen bonds are shown as dashed lines; only H atoms involved in interactions are shown.

Crystal data

C₂₈H₃₃N₂O₂P	F(000) = 984
M_r = 460.53	D_x = 1.222 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2411 reflections
a = 14.640 (7) Å	θ = 2.2–20.0°
b = 11.656 (5) Å	µ = 0.14 mm⁻¹
c = 14.998 (7) Å	T = 297 K
β = 101.950 (9)°	Block, colourless
V = 2504 (2) Å³	0.30 × 0.26 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4412 independent reflections
Radiation source: fine-focus sealed tube	3184 reflections with I > 2σ(I)
graphite	R_int = 0.099
phi and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→17
T_min = 0.960, T_max = 0.984	k = −13→13
17694 measured reflections	l = −17→17

Refinement

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)] = 0.112	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.207	H-atom parameters constrained
S = 1.23	w = 1/[σ²(F_o²) + (0.0459P)² + 3.678P] where P = (F_o² + 2F_c²)/3
4412 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Special details

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.

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

	x	y	z	U_iso*/U_eq
C1	0.8291 (3)	0.6869 (4)	0.0252 (3)	0.0286 (11)
C2	0.8999 (3)	0.6704 (4)	0.1032 (3)	0.0331 (11)
C3	0.9912 (4)	0.6862 (4)	0.0965 (4)	0.0433 (14)
H3	1.0382	0.6763	0.1481	0.052*
C4	1.0150 (4)	0.7158 (5)	0.0161 (4)	0.0469 (14)
H4	1.0774	0.7250	0.0132	0.056*
C5	0.9466 (4)	0.7320 (5)	−0.0602 (4)	0.0475 (15)
H5	0.9623	0.7521	−0.1152	0.057*
C6	0.8551 (3)	0.7185 (4)	−0.0550 (3)	0.0360 (12)
H6	0.8090	0.7308	−0.1069	0.043*
C7	0.8755 (3)	0.6394 (4)	0.1929 (3)	0.0358 (12)
H7A	0.9324	0.6350	0.2392	0.043*
H7B	0.8370	0.6997	0.2103	0.043*
C8	0.7893 (4)	0.5140 (5)	0.2711 (4)	0.0552 (16)
H8A	0.7469	0.5761	0.2772	0.066*
H8B	0.8401	0.5149	0.3242	0.066*
C9	0.7389 (5)	0.4023 (5)	0.2665 (5)	0.070 (2)
H9A	0.7151	0.3923	0.3218	0.084*
H9B	0.6859	0.4038	0.2155	0.084*
C10	0.8860 (4)	0.4335 (4)	0.1789 (4)	0.0460 (14)
H10A	0.9397	0.4319	0.2291	0.055*
H10B	0.9084	0.4420	0.1227	0.055*
C11	0.8324 (4)	0.3235 (4)	0.1766 (4)	0.0540 (16)
H11A	0.7811	0.3238	0.1240	0.065*
H11B	0.8730	0.2597	0.1699	0.065*
C12	0.6424 (3)	0.7480 (4)	−0.0629 (3)	0.0355 (12)
C13	0.6155 (3)	0.8617 (4)	−0.0499 (4)	0.0397 (13)
C14	0.5645 (4)	0.9221 (5)	−0.1217 (4)	0.0568 (16)
H14	0.5491	0.9979	−0.1125	0.068*
C15	0.5352 (4)	0.8745 (6)	−0.2073 (5)	0.070 (2)
H15	0.4995	0.9165	−0.2547	0.085*
C16	0.5607 (4)	0.7625 (7)	−0.2202 (4)	0.072 (2)
H16	0.5423	0.7280	−0.2770	0.086*
C17	0.6126 (4)	0.7027 (5)	−0.1497 (4)	0.0507 (15)
H17	0.6291	0.6276	−0.1602	0.061*
C18	0.6392 (4)	0.9177 (5)	0.0427 (4)	0.0457 (14)
H18A	0.6131	0.9945	0.0379	0.055*
H18B	0.6094	0.8748	0.0842	0.055*
C19	0.7540 (4)	0.9681 (5)	0.1751 (4)	0.0569 (16)
H19A	0.7243	0.9175	0.2118	0.068*
H19B	0.7264	1.0437	0.1757	0.068*
C20	0.8568 (4)	0.9748 (6)	0.2152 (4)	0.0660 (18)
H20A	0.8661	1.0056	0.2765	0.079*
H20B	0.8833	0.8983	0.2190	0.079*
C21	0.7873 (4)	0.9979 (5)	0.0286 (4)	0.0478 (14)
H21A	0.7616	1.0749	0.0252	0.057*
H21B	0.7791	0.9682	−0.0330	0.057*
C22	0.8891 (4)	1.0021 (5)	0.0712 (4)	0.0543 (16)
H22A	0.9154	0.9256	0.0720	0.065*
H22B	0.9210	1.0509	0.0350	0.065*
C23	0.6850 (3)	0.5187 (4)	−0.0066 (3)	0.0347 (12)
C24	0.7352 (4)	0.4612 (5)	−0.0615 (4)	0.0481 (14)
H24	0.7852	0.4978	−0.0788	0.058*
C25	0.7123 (4)	0.3509 (5)	−0.0911 (4)	0.0590 (17)
H25	0.7456	0.3143	−0.1293	0.071*
C26	0.6405 (4)	0.2956 (5)	−0.0640 (5)	0.0633 (19)
H26	0.6251	0.2210	−0.0835	0.076*
C27	0.5907 (4)	0.3504 (5)	−0.0075 (5)	0.0669 (19)
H27	0.5421	0.3125	0.0114	0.080*
C28	0.6129 (4)	0.4608 (5)	0.0209 (4)	0.0481 (14)
H28	0.5792	0.4971	0.0589	0.058*
N1	0.8259 (3)	0.5307 (3)	0.1898 (3)	0.0336 (10)
N2	0.7376 (3)	0.9253 (3)	0.0814 (3)	0.0354 (10)
O1	0.7968 (3)	0.3077 (3)	0.2563 (3)	0.0681 (13)
O2	0.9036 (3)	1.0454 (3)	0.1617 (3)	0.0595 (11)
P1	0.70675 (9)	0.66657 (11)	0.03556 (9)	0.0311 (3)

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.028 (2)	0.021 (3)	0.037 (3)	0.001 (2)	0.008 (2)	0.000 (2)
C2	0.040 (3)	0.020 (3)	0.037 (3)	−0.002 (2)	0.002 (2)	0.005 (2)
C3	0.045 (3)	0.030 (3)	0.051 (4)	0.001 (2)	0.000 (3)	0.007 (3)
C4	0.028 (3)	0.050 (4)	0.064 (4)	0.002 (3)	0.014 (3)	0.014 (3)
C5	0.044 (3)	0.060 (4)	0.044 (3)	0.005 (3)	0.021 (3)	0.018 (3)
C6	0.039 (3)	0.038 (3)	0.032 (3)	0.002 (2)	0.007 (2)	0.005 (2)
C7	0.048 (3)	0.031 (3)	0.025 (3)	−0.003 (2)	0.001 (2)	−0.007 (2)
C8	0.083 (4)	0.040 (3)	0.051 (4)	0.007 (3)	0.032 (3)	0.009 (3)
C9	0.099 (5)	0.059 (4)	0.068 (5)	0.001 (4)	0.054 (4)	0.010 (4)
C10	0.055 (4)	0.036 (3)	0.046 (3)	0.002 (3)	0.007 (3)	0.002 (3)
C11	0.076 (4)	0.027 (3)	0.062 (4)	0.001 (3)	0.022 (3)	0.004 (3)
C12	0.026 (3)	0.037 (3)	0.043 (3)	0.003 (2)	0.007 (2)	−0.004 (3)
C13	0.023 (3)	0.045 (3)	0.050 (3)	−0.001 (2)	0.007 (2)	−0.003 (3)
C14	0.049 (4)	0.050 (4)	0.068 (4)	0.013 (3)	0.004 (3)	0.004 (3)
C15	0.050 (4)	0.082 (5)	0.071 (5)	0.018 (4)	−0.005 (3)	0.020 (4)
C16	0.060 (4)	0.100 (6)	0.047 (4)	0.015 (4)	−0.008 (3)	−0.006 (4)
C17	0.047 (3)	0.055 (4)	0.044 (4)	0.008 (3)	−0.005 (3)	−0.011 (3)
C18	0.042 (3)	0.037 (3)	0.062 (4)	0.006 (3)	0.019 (3)	−0.007 (3)
C19	0.066 (4)	0.058 (4)	0.053 (4)	−0.010 (3)	0.025 (3)	−0.007 (3)
C20	0.077 (5)	0.067 (4)	0.053 (4)	−0.022 (4)	0.012 (4)	−0.012 (3)
C21	0.052 (4)	0.037 (3)	0.056 (4)	−0.005 (3)	0.013 (3)	0.007 (3)
C22	0.057 (4)	0.040 (4)	0.068 (4)	−0.007 (3)	0.020 (3)	−0.002 (3)
C23	0.031 (3)	0.035 (3)	0.035 (3)	0.005 (2)	−0.001 (2)	0.002 (2)
C24	0.049 (3)	0.047 (4)	0.049 (4)	−0.002 (3)	0.010 (3)	−0.011 (3)
C25	0.056 (4)	0.051 (4)	0.068 (4)	0.005 (3)	0.009 (3)	−0.023 (3)
C26	0.049 (4)	0.036 (3)	0.094 (5)	−0.003 (3)	−0.009 (4)	−0.023 (3)
C27	0.043 (4)	0.051 (4)	0.107 (6)	−0.008 (3)	0.015 (4)	0.002 (4)
C28	0.041 (3)	0.036 (3)	0.066 (4)	0.002 (3)	0.007 (3)	0.000 (3)
N1	0.047 (3)	0.025 (2)	0.030 (2)	0.0021 (19)	0.0089 (19)	0.0011 (18)
N2	0.041 (3)	0.035 (2)	0.032 (2)	0.002 (2)	0.011 (2)	−0.0034 (19)
O1	0.107 (4)	0.040 (2)	0.066 (3)	0.005 (2)	0.040 (3)	0.018 (2)
O2	0.059 (3)	0.039 (2)	0.075 (3)	−0.012 (2)	0.003 (2)	−0.010 (2)
P1	0.0313 (7)	0.0320 (7)	0.0314 (7)	0.0006 (6)	0.0097 (5)	−0.0040 (6)

Geometric parameters (Å, °)

C1—C6	1.385 (6)	C14—H14	0.9300
C1—C2	1.407 (6)	C15—C16	1.382 (9)
C1—P1	1.845 (5)	C15—H15	0.9300
C2—C3	1.374 (7)	C16—C17	1.360 (8)
C2—C7	1.505 (6)	C16—H16	0.9300
C3—C4	1.367 (7)	C17—H17	0.9300
C3—H3	0.9300	C18—N2	1.439 (6)
C4—C5	1.368 (7)	C18—H18A	0.9700
C4—H4	0.9300	C18—H18B	0.9700
C5—C6	1.366 (7)	C19—N2	1.463 (6)
C5—H5	0.9300	C19—C20	1.502 (8)
C6—H6	0.9300	C19—H19A	0.9700
C7—N1	1.456 (6)	C19—H19B	0.9700
C7—H7A	0.9700	C20—O2	1.420 (7)
C7—H7B	0.9700	C20—H20A	0.9700
C8—N1	1.444 (6)	C20—H20B	0.9700
C8—C9	1.491 (8)	C21—N2	1.454 (6)
C8—H8A	0.9700	C21—C22	1.496 (7)
C8—H8B	0.9700	C21—H21A	0.9700
C9—O1	1.418 (7)	C21—H21B	0.9700
C9—H9A	0.9700	C22—O2	1.423 (6)
C9—H9B	0.9700	C22—H22A	0.9700
C10—N1	1.465 (6)	C22—H22B	0.9700
C10—C11	1.499 (7)	C23—C24	1.385 (7)
C10—H10A	0.9700	C23—C28	1.385 (7)
C10—H10B	0.9700	C23—P1	1.841 (5)
C11—O1	1.413 (6)	C24—C25	1.379 (7)
C11—H11A	0.9700	C24—H24	0.9300
C11—H11B	0.9700	C25—C26	1.364 (8)
C12—C17	1.390 (7)	C25—H25	0.9300
C12—C13	1.407 (7)	C26—C27	1.384 (8)
C12—P1	1.842 (5)	C26—H26	0.9300
C13—C14	1.371 (7)	C27—C28	1.373 (8)
C13—C18	1.510 (7)	C27—H27	0.9300
C14—C15	1.383 (8)	C28—H28	0.9300

C6—C1—C2	118.1 (4)	C16—C17—C12	123.4 (6)
C6—C1—P1	123.6 (4)	C16—C17—H17	118.3
C2—C1—P1	118.2 (4)	C12—C17—H17	118.3
C3—C2—C1	118.7 (4)	N2—C18—C13	114.7 (4)
C3—C2—C7	120.9 (4)	N2—C18—H18A	108.6
C1—C2—C7	120.4 (4)	C13—C18—H18A	108.6
C4—C3—C2	121.9 (5)	N2—C18—H18B	108.6
C4—C3—H3	119.1	C13—C18—H18B	108.6
C2—C3—H3	119.1	H18A—C18—H18B	107.6
C3—C4—C5	119.8 (5)	N2—C19—C20	110.8 (5)
C3—C4—H4	120.1	N2—C19—H19A	109.5
C5—C4—H4	120.1	C20—C19—H19A	109.5
C6—C5—C4	119.5 (5)	N2—C19—H19B	109.5
C6—C5—H5	120.2	C20—C19—H19B	109.5
C4—C5—H5	120.2	H19A—C19—H19B	108.1
C5—C6—C1	122.0 (5)	O2—C20—C19	111.3 (5)
C5—C6—H6	119.0	O2—C20—H20A	109.4
C1—C6—H6	119.0	C19—C20—H20A	109.4
N1—C7—C2	113.0 (4)	O2—C20—H20B	109.4
N1—C7—H7A	109.0	C19—C20—H20B	109.4
C2—C7—H7A	109.0	H20A—C20—H20B	108.0
N1—C7—H7B	109.0	N2—C21—C22	110.7 (5)
C2—C7—H7B	109.0	N2—C21—H21A	109.5
H7A—C7—H7B	107.8	C22—C21—H21A	109.5
N1—C8—C9	110.2 (5)	N2—C21—H21B	109.5
N1—C8—H8A	109.6	C22—C21—H21B	109.5
C9—C8—H8A	109.6	H21A—C21—H21B	108.1
N1—C8—H8B	109.6	O2—C22—C21	110.9 (5)
C9—C8—H8B	109.6	O2—C22—H22A	109.5
H8A—C8—H8B	108.1	C21—C22—H22A	109.5
O1—C9—C8	112.5 (5)	O2—C22—H22B	109.5
O1—C9—H9A	109.1	C21—C22—H22B	109.5
C8—C9—H9A	109.1	H22A—C22—H22B	108.0
O1—C9—H9B	109.1	C24—C23—C28	118.2 (5)
C8—C9—H9B	109.1	C24—C23—P1	125.6 (4)
H9A—C9—H9B	107.8	C28—C23—P1	116.3 (4)
N1—C10—C11	109.9 (4)	C25—C24—C23	121.3 (5)
N1—C10—H10A	109.7	C25—C24—H24	119.4
C11—C10—H10A	109.7	C23—C24—H24	119.4
N1—C10—H10B	109.7	C26—C25—C24	119.7 (6)
C11—C10—H10B	109.7	C26—C25—H25	120.1
H10A—C10—H10B	108.2	C24—C25—H25	120.1
O1—C11—C10	112.1 (5)	C25—C26—C27	120.0 (6)
O1—C11—H11A	109.2	C25—C26—H26	120.0
C10—C11—H11A	109.2	C27—C26—H26	120.0
O1—C11—H11B	109.2	C28—C27—C26	120.1 (6)
C10—C11—H11B	109.2	C28—C27—H27	119.9
H11A—C11—H11B	107.9	C26—C27—H27	119.9
C17—C12—C13	116.4 (5)	C27—C28—C23	120.7 (6)
C17—C12—P1	124.4 (4)	C27—C28—H28	119.6
C13—C12—P1	119.1 (4)	C23—C28—H28	119.6
C14—C13—C12	119.9 (5)	C8—N1—C7	111.1 (4)
C14—C13—C18	119.0 (5)	C8—N1—C10	109.1 (4)
C12—C13—C18	121.1 (5)	C7—N1—C10	111.7 (4)
C13—C14—C15	122.5 (6)	C18—N2—C21	112.8 (4)
C13—C14—H14	118.8	C18—N2—C19	111.1 (4)
C15—C14—H14	118.8	C21—N2—C19	108.9 (4)
C16—C15—C14	117.9 (6)	C11—O1—C9	108.9 (4)
C16—C15—H15	121.0	C20—O2—C22	109.9 (4)
C14—C15—H15	121.0	C23—P1—C12	100.6 (2)
C17—C16—C15	119.9 (6)	C23—P1—C1	101.2 (2)
C17—C16—H16	120.0	C12—P1—C1	102.2 (2)
C15—C16—H16	120.0

C6—C1—C2—C3	−0.1 (7)	C24—C25—C26—C27	0.3 (9)
P1—C1—C2—C3	−179.5 (4)	C25—C26—C27—C28	0.5 (10)
C6—C1—C2—C7	178.3 (4)	C26—C27—C28—C23	0.1 (9)
P1—C1—C2—C7	−1.2 (6)	C24—C23—C28—C27	−1.4 (8)
C1—C2—C3—C4	−0.8 (7)	P1—C23—C28—C27	179.5 (4)
C7—C2—C3—C4	−179.2 (5)	C9—C8—N1—C7	−180.0 (5)
C2—C3—C4—C5	0.8 (8)	C9—C8—N1—C10	−56.4 (6)
C3—C4—C5—C6	0.1 (8)	C2—C7—N1—C8	−169.7 (4)
C4—C5—C6—C1	−1.0 (8)	C2—C7—N1—C10	68.2 (5)
C2—C1—C6—C5	1.0 (7)	C11—C10—N1—C8	56.4 (6)
P1—C1—C6—C5	−179.6 (4)	C11—C10—N1—C7	179.7 (4)
C3—C2—C7—N1	−120.4 (5)	C13—C18—N2—C21	64.1 (6)
C1—C2—C7—N1	61.3 (6)	C13—C18—N2—C19	−173.4 (5)
N1—C8—C9—O1	58.5 (7)	C22—C21—N2—C18	−179.5 (4)
N1—C10—C11—O1	−58.3 (6)	C22—C21—N2—C19	56.6 (6)
C17—C12—C13—C14	−1.4 (7)	C20—C19—N2—C18	179.5 (5)
P1—C12—C13—C14	−177.5 (4)	C20—C19—N2—C21	−55.6 (6)
C17—C12—C13—C18	176.6 (5)	C10—C11—O1—C9	57.8 (7)
P1—C12—C13—C18	0.5 (6)	C8—C9—O1—C11	−57.9 (7)
C12—C13—C14—C15	2.1 (9)	C19—C20—O2—C22	−58.0 (6)
C18—C13—C14—C15	−176.0 (5)	C21—C22—O2—C20	58.9 (6)
C13—C14—C15—C16	−1.5 (10)	C24—C23—P1—C12	83.7 (5)
C14—C15—C16—C17	0.3 (10)	C28—C23—P1—C12	−97.4 (4)
C15—C16—C17—C12	0.3 (10)	C24—C23—P1—C1	−21.1 (5)
C13—C12—C17—C16	0.3 (8)	C28—C23—P1—C1	157.8 (4)
P1—C12—C17—C16	176.2 (5)	C17—C12—P1—C23	−16.0 (5)
C14—C13—C18—N2	−121.9 (5)	C13—C12—P1—C23	159.8 (4)
C12—C13—C18—N2	60.1 (6)	C17—C12—P1—C1	88.0 (5)
N2—C19—C20—O2	57.3 (7)	C13—C12—P1—C1	−96.2 (4)
N2—C21—C22—O2	−59.1 (6)	C6—C1—P1—C23	83.1 (4)
C28—C23—C24—C25	2.3 (8)	C2—C1—P1—C23	−97.4 (4)
P1—C23—C24—C25	−178.8 (4)	C6—C1—P1—C12	−20.4 (4)
C23—C24—C25—C26	−1.8 (9)	C2—C1—P1—C12	159.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···O1ⁱ	0.93	2.46	3.370 (8)	166
C11—H11B···O2ⁱⁱ	0.97	2.55	3.426 (6)	151

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2178).

References

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