[1,2-Bis(diphenyl­phosphan­yl)ethane-κ2P,P′]{2-[(4-nitro­benzoyl­meth­yl)diphenyl­phosphan­yl]phenyl-κ2C,C′}palladium(II) trifluoro­methane­sulfonate–dichloro­methane–n-hexane (1/1/0.5)

Rizzoli, C.; Karami, K.; Borzooie, F.

doi:10.1107/S1600536811008075

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m416-m417

doi:10.1107/S1600536811008075

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[1,2-Bis(diphenylphosphanyl)ethane-κ²P,P′]{2-[(4-nitrobenzoylmethyl)diphenylphosphanyl]phenyl-κ²C,C′}palladium(II) trifluoromethanesulfonate–dichloromethane–n-hexane (1/1/0.5)

Corrado Rizzoli,^a ^* Kazem Karami ^b and Farzaneh Borzooie ^b

^aDipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Universitá degli Studi di Parma, Viale G. P. Usberti 17/A, I-43124 Parma, Italy, and ^bDepartment of Chemistry, Isfahan University of Technology, Isfahan 84156/83111, Iran
^*Correspondence e-mail: corrado.rizzoli@unipr.it

(Received 25 February 2011; accepted 3 March 2011; online 9 March 2011)

In the cation of the title compound, [Pd(C₂₆H₁₉NO₃P)(C₂₆H₂₄P₂)]CF₃O₃S·CH₂Cl₂·0.5C₆H₁₄, the Pd^II atom has a slightly tetrahedrally distorted square-planar coordination geometry. The PdC₃P and PdC₂P₂ five-membered metallacycles adopt envelope and twist conformations, respectively. In the crystal, intermolecular C—H⋯O hydrogen bonds link cations and anions into a three-dimensional network. The dichloromethane solvent molecule is disordered over three orientations with a site-occupancy ratio of 0.5/0.3/0.2. The n-hexane solvent molecule has a crystallographically imposed centre of symmetry.

Related literature

For the synthesis and applications as catalysts of cyclopalladated metal complexes, see: Rietling et al. (2002 ); Aguilar et al. (2008 ); Dupont et al. (2001 ); Chen et al. (2009 ). For ortho-palladated α-ketophosphorus ylides complexes reported by our group, see: Karami et al. (2010 ); Karami, Rizzoli & Salah (2011 ); Karami, Rizzoli & Borzooie (2011 ). For related structures, see: Falvello et al. (1998 , 1999 ); Shao et al. (1982 ).

Experimental

Crystal data

[Pd(C₂₆H₁₉NO₃P)(C₂₆H₂₄P₂)]CF₃O₃S·CH₂Cl₂·0.5C₆H₁₄
M_r = 1206.27
Monoclinic, P 2₁ /n
a = 12.4063 (7) Å
b = 14.2445 (8) Å
c = 31.3633 (17) Å
β = 91.6675 (9)°
V = 5540.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.62 mm⁻¹
T = 294 K
0.19 × 0.16 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.872, T_max = 0.955
62924 measured reflections
10529 independent reflections
8106 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.076
S = 1.04
10529 reflections
691 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O1ⁱ	0.93	2.54	3.284 (3)	138
C30—H30⋯O6ⁱⁱ	0.93	2.55	3.372 (4)	148
C39—H39B⋯O6ⁱⁱⁱ	0.97	2.59	3.309 (4)	131
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y-1, z; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and SCHAKAL97 (Keller, 1997 ); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008075/zj2004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008075/zj2004Isup2.hkl

checkCIF report

Comment top

The synthesis and characterization of cyclopalladated metal complexes (Rietling et al., 2002) has attracted considerable attention due to their potential applications in organic synthesis and homogenous catalysis (Aguilar et al., 2008; Dupont et al., 2001; Chen et al., 2009). As a continuation of our ongoing project devoted to the development of new catalysts based on ortho-palladated α-ketophosphorus ylides complexes (Karami et al., 2010; Karami, Rizzoli & Salah, 2011; Karami, Rizzoli & Borzooie, 2011), we report herein the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) consists of one mononuclear complex cation, one trifluoromethanesulfonate anion, one disordered dichloromethane molecule and half an n-hexane lying on a centre of symmetry. In the cation (Fig. 2), the palladium(II) atom displays a slightly but not negligibly tetrahedrally distorted square planar coordination geometry, with atoms P2, P3, C1 and C9 displaced from the mean plane through the P₂C₂ core by -0.0061 (6), 0.0055 (6), -0.070 (2) and 0.069 (2) Å, respectively. The distortion from the regular square planar geometry is also indicated by the values of the cis and trans angles subtended at the metal, which range from 83.17 (8) to 100.49 (5)°, and from 175.31 (5) to 175.68 (5)°, respectively. The Pd–C bond lengths involving the aromatic and ylidic carbon atoms (Pd1–C9 = 2.0783 (19) Å; Pd–C1 = 2.1711 (19) Å) are in agreement with those observed in related cyclopalladated complexes (Falvello et al., 1998; Falvello et al., 1999; Karami et al., 2010; Karami, Rizzoli & Salah, 2011; Karami, Rizzoli & Borzooie, 2011). The P1–C1 bond length (1.768 (2) Å) is significantly longer than that observed in the related free ylide (1.711 Å) of formula PPh₃C(H)COPh (Shao et al., 1982). The Pd1···P1 separation is 3.0241 (9) Å. The PdC₃P five-membered metallacycle (Pd1/C9/C14/P1/C1) assumes an envelope conformation, with atom C1 displaced by 1.006 (2) Å from the mean planes of the remaining four atoms, whereas the PdC₂P₂ metallacycle (Pd1/P2/C39/C40/P3) adopts a twist conformation with the local twofold axis passing through the C39–C40 bond and the Pd atom. In the crystal structure (Fig. 3), cations and anions are linked into a three-dimensional network by intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For the synthesis and applications as catalysts of cyclopalladated metal complexes, see: Rietling et al. (2002); Aguilar et al. (2008); Dupont et al. (2001); Chen et al. (2009). For ortho-palladated α-ketophosphorus ylides complexes reported by our group, see: Karami et al. (2010); Karami, Rizzoli & Salah (2011); Karami, Rizzoli & Borzooie (2011). For related structures, see: Falvello et al. (1998, 1999); Shao et al. (1982).

Experimental top

The title compound was obtained according to the procedure recently reported elsewhere (Karami, Rizzoli & Borzooie, 2011). Crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane/n-hexane (1:1 v/v) solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL97 (Keller, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST95 (Nardelli, 1995).

Figures top

	Fig. 1. The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 30% probability level. Only the major component of the disordered dichloromethane molecule is shown. Symmetry code: (i) -x, 1 - y, -z.
	Fig. 2. The cation of the title compound, showing the labelling scheme adopted. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are omitted for clarity.
	Fig. 3. Crystal packing of the title compound approximately viewed along the a axis. Only the major component of the disordered dichloromethane molecule is shown. Hydrogen atoms not involved in intermolecular C—H···O hydrogen bonds (dashed lines) are omitted for clarity.

[1,2-Bis(diphenylphosphanyl)ethane-κ²P,P']{2-[(4- nitrobenzoylmethyl)diphenylphosphanyl]phenyl- κ²C,C'}palladium(II) trifluoromethanesulfonate–dichloromethane–n-hexane (1/1/0.5) top

Crystal data top

[Pd(C₂₆H₁₉NO₃P)(C₂₆H₂₄P₂)]CF₃O₃S·CH₂Cl₂·0.5C₆H₁₄	F(000) = 2468
M_r = 1206.27	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1226 reflections
a = 12.4063 (7) Å	θ = 6.3–23.4°
b = 14.2445 (8) Å	µ = 0.62 mm⁻¹
c = 31.3633 (17) Å	T = 294 K
β = 91.6675 (9)°	Irregular block, yellow
V = 5540.2 (5) Å³	0.19 × 0.16 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	10529 independent reflections
Radiation source: fine-focus sealed tube	8106 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 25.7°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
T_min = 0.872, T_max = 0.955	k = −17→17
62924 measured reflections	l = −38→38

Refinement top

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.038P)²] where P = (F_o² + 2F_c²)/3
10529 reflections	(Δ/σ)_max = 0.001
691 parameters	Δρ_max = 0.37 e Å⁻³
14 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Pd(C₂₆H₁₉NO₃P)(C₂₆H₂₄P₂)]CF₃O₃S·CH₂Cl₂·0.5C₆H₁₄	V = 5540.2 (5) Å³
M_r = 1206.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.4063 (7) Å	µ = 0.62 mm⁻¹
b = 14.2445 (8) Å	T = 294 K
c = 31.3633 (17) Å	0.19 × 0.16 × 0.10 mm
β = 91.6675 (9)°

Data collection top

Bruker APEXII CCD diffractometer	10529 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	8106 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.955	R_int = 0.036
62924 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	14 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.04	Δρ_max = 0.37 e Å⁻³
10529 reflections	Δρ_min = −0.38 e Å⁻³
691 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pd1	0.756229 (11)	0.147230 (10)	0.131977 (5)	0.03814 (6)
S1	0.90642 (7)	0.50943 (6)	0.15555 (3)	0.0883 (2)
P1	0.81951 (4)	0.14269 (4)	0.039724 (17)	0.04289 (13)
P3	0.57524 (4)	0.14972 (4)	0.152637 (18)	0.04526 (13)
P2	0.78566 (4)	0.07474 (4)	0.196011 (17)	0.04514 (14)
O1	0.57447 (13)	0.19304 (12)	0.03587 (6)	0.0709 (5)
O2	0.5578 (3)	0.68752 (18)	0.07768 (10)	0.1340 (10)
O3	0.4015 (3)	0.6445 (2)	0.06026 (13)	0.1685 (14)
O4	0.8765 (2)	0.57210 (17)	0.12237 (9)	0.1226 (8)
O5	0.82523 (18)	0.44856 (18)	0.17003 (8)	0.1183 (8)
O6	0.9700 (3)	0.5548 (2)	0.18984 (9)	0.1499 (11)
F1	0.9555 (2)	0.3873 (2)	0.09940 (9)	0.1675 (11)
F2	1.0418 (2)	0.37281 (17)	0.16085 (10)	0.1651 (11)
F3	1.08767 (16)	0.47955 (15)	0.11854 (7)	0.1293 (7)
N1	0.4919 (3)	0.6307 (2)	0.06826 (9)	0.0947 (9)
C1	0.74213 (16)	0.21915 (14)	0.07104 (6)	0.0428 (5)
H1	0.7844	0.2770	0.0742	0.051*
C2	0.63523 (17)	0.24779 (16)	0.05422 (7)	0.0487 (5)
C3	0.60121 (18)	0.34836 (15)	0.05941 (7)	0.0524 (5)
C4	0.6672 (2)	0.41801 (17)	0.07639 (9)	0.0697 (7)
H4	0.7363	0.4030	0.0865	0.084*
C5	0.6311 (3)	0.51037 (18)	0.07854 (10)	0.0794 (8)
H5	0.6762	0.5574	0.0893	0.095*
C6	0.5308 (3)	0.53044 (19)	0.06495 (9)	0.0731 (7)
C7	0.4620 (2)	0.4644 (2)	0.04858 (9)	0.0828 (9)
H7	0.3923	0.4807	0.0397	0.099*
C8	0.4971 (2)	0.37316 (19)	0.04537 (8)	0.0694 (7)
H8	0.4513	0.3276	0.0338	0.083*
C9	0.91717 (15)	0.13543 (13)	0.11614 (6)	0.0398 (5)
C10	1.00786 (17)	0.12915 (15)	0.14348 (7)	0.0502 (5)
H10	0.9988	0.1295	0.1728	0.060*
C11	1.11043 (17)	0.12245 (18)	0.12802 (8)	0.0608 (6)
H11	1.1689	0.1186	0.1472	0.073*
C12	1.12825 (18)	0.12141 (18)	0.08535 (8)	0.0641 (7)
H12	1.1981	0.1167	0.0755	0.077*
C13	1.04155 (18)	0.12737 (16)	0.05688 (7)	0.0545 (6)
H13	1.0521	0.1268	0.0276	0.065*
C14	0.93907 (16)	0.13423 (14)	0.07244 (6)	0.0424 (5)
C15	0.76628 (17)	0.02642 (16)	0.03113 (6)	0.0490 (5)
C16	0.8100 (2)	−0.04862 (17)	0.05335 (8)	0.0621 (6)
H16	0.8659	−0.0395	0.0733	0.074*
C17	0.7694 (3)	−0.13839 (18)	0.04549 (10)	0.0845 (9)
H17	0.7980	−0.1894	0.0604	0.101*
C18	0.6875 (3)	−0.1518 (2)	0.01586 (11)	0.0873 (10)
H18	0.6610	−0.2120	0.0108	0.105*
C19	0.6445 (2)	−0.0779 (2)	−0.00625 (9)	0.0789 (8)
H19	0.5893	−0.0877	−0.0264	0.095*
C20	0.68299 (19)	0.01173 (19)	0.00130 (7)	0.0618 (6)
H20	0.6531	0.0623	−0.0136	0.074*
C21	0.84920 (18)	0.18697 (18)	−0.01227 (7)	0.0545 (6)
C22	0.8883 (2)	0.1285 (2)	−0.04356 (8)	0.0712 (7)
H22	0.8942	0.0643	−0.0384	0.085*
C23	0.9187 (2)	0.1647 (3)	−0.08236 (9)	0.0815 (9)
H23	0.9486	0.1252	−0.1025	0.098*
C24	0.9057 (3)	0.2541 (3)	−0.09099 (11)	0.1113 (12)
H24	0.9286	0.2781	−0.1168	0.134*
C25	0.8589 (3)	0.3115 (3)	−0.06240 (12)	0.1215 (13)
H25	0.8428	0.3732	−0.0699	0.146*
C26	0.8347 (3)	0.2789 (2)	−0.02164 (10)	0.1082 (12)
H26	0.8090	0.3199	−0.0013	0.130*
C27	0.85865 (19)	−0.03586 (15)	0.19613 (7)	0.0533 (6)
C28	0.8165 (2)	−0.10762 (19)	0.17098 (9)	0.0715 (7)
H28	0.7543	−0.0974	0.1544	0.086*
C29	0.8663 (3)	−0.1941 (2)	0.17036 (11)	0.0857 (9)
H29	0.8370	−0.2422	0.1537	0.103*
C30	0.9574 (3)	−0.2089 (2)	0.19399 (11)	0.0962 (11)
H30	0.9903	−0.2675	0.1937	0.115*
C31	1.0012 (3)	−0.1393 (3)	0.21797 (11)	0.1123 (13)
H31	1.0649	−0.1501	0.2336	0.135*
C32	0.9523 (2)	−0.0517 (2)	0.21953 (9)	0.0830 (8)
H32	0.9827	−0.0042	0.2363	0.100*
C33	0.84562 (17)	0.15069 (15)	0.23661 (7)	0.0498 (5)
C34	0.8534 (2)	0.1220 (2)	0.27935 (8)	0.0698 (7)
H34	0.8303	0.0625	0.2871	0.084*
C35	0.8953 (2)	0.1821 (3)	0.30950 (9)	0.0839 (9)
H35	0.8999	0.1634	0.3379	0.101*
C36	0.9302 (2)	0.2687 (3)	0.29844 (10)	0.0884 (9)
H36	0.9601	0.3082	0.3192	0.106*
C37	0.9221 (2)	0.2985 (2)	0.25752 (10)	0.0777 (8)
H37	0.9457	0.3583	0.2504	0.093*
C38	0.87898 (18)	0.24007 (17)	0.22645 (8)	0.0581 (6)
H38	0.8723	0.2611	0.1984	0.070*
C39	0.65511 (18)	0.04531 (17)	0.21851 (7)	0.0572 (6)
H39A	0.6257	−0.0108	0.2050	0.069*
H39B	0.6635	0.0338	0.2489	0.069*
C40	0.58024 (18)	0.12801 (17)	0.21030 (7)	0.0556 (6)
H40A	0.6071	0.1831	0.2254	0.067*
H40B	0.5087	0.1138	0.2202	0.067*
C41	0.48826 (17)	0.25194 (16)	0.14711 (7)	0.0513 (5)
C42	0.5253 (2)	0.33604 (18)	0.16386 (9)	0.0713 (7)
H42	0.5942	0.3398	0.1762	0.086*
C43	0.4591 (3)	0.4154 (2)	0.16227 (9)	0.0848 (9)
H43	0.4840	0.4720	0.1736	0.102*
C44	0.3585 (3)	0.4099 (2)	0.14422 (11)	0.0940 (10)
H44	0.3141	0.4625	0.1439	0.113*
C45	0.3215 (2)	0.3273 (2)	0.12634 (12)	0.0943 (10)
H45	0.2533	0.3243	0.1133	0.113*
C46	0.38683 (19)	0.24915 (19)	0.12800 (9)	0.0733 (7)
H46	0.3620	0.1932	0.1160	0.088*
C47	0.49623 (16)	0.04970 (15)	0.13374 (7)	0.0484 (5)
C48	0.40033 (18)	0.02404 (18)	0.15241 (9)	0.0669 (7)
H48	0.3732	0.0610	0.1741	0.080*
C49	0.3453 (2)	−0.05461 (19)	0.13946 (9)	0.0732 (7)
H49	0.2799	−0.0693	0.1516	0.088*
C50	0.3860 (2)	−0.11248 (18)	0.10840 (9)	0.0661 (7)
H50	0.3497	−0.1669	0.1001	0.079*
C51	0.4797 (2)	−0.08836 (18)	0.09037 (8)	0.0662 (7)
H51	0.5077	−0.1269	0.0694	0.079*
C52	0.53468 (18)	−0.00806 (16)	0.10225 (7)	0.0554 (6)
H52	0.5983	0.0074	0.0889	0.067*
C53	1.0025 (3)	0.4339 (3)	0.13228 (13)	0.1008 (10)
C54A	0.3163 (9)	0.6781 (8)	0.2291 (3)	0.194 (5)	0.50
H54A	0.2741	0.7264	0.2427	0.232*	0.50
H54B	0.3922	0.6927	0.2334	0.232*	0.50
Cl1A	0.2831 (3)	0.6713 (2)	0.17539 (14)	0.1998 (15)	0.50
Cl2A	0.2875 (4)	0.5690 (5)	0.25025 (15)	0.288 (3)	0.50
C54B	0.2090 (16)	0.6089 (8)	0.2196 (4)	0.141 (6)*	0.30
H54C	0.2623	0.6138	0.1977	0.170*	0.30
H54D	0.1382	0.6202	0.2067	0.170*	0.30
Cl1B	0.2144 (9)	0.4956 (6)	0.2440 (3)	0.295 (5)*	0.30
Cl2B	0.2361 (6)	0.6898 (5)	0.2604 (2)	0.198 (2)*	0.30
C54C	0.2675 (17)	0.7357 (9)	0.2117 (4)	0.107 (6)*	0.20
H54E	0.3340	0.7619	0.2013	0.129*	0.20
H54F	0.2060	0.7657	0.1976	0.129*	0.20
Cl1C	0.2632 (13)	0.6113 (9)	0.2074 (5)	0.245 (6)*	0.20
Cl2C	0.2614 (9)	0.7397 (8)	0.2671 (3)	0.207 (4)*	0.20
C55	0.1874 (6)	0.3580 (5)	0.0169 (3)	0.281 (5)
H55A	0.2628	0.3594	0.0248	0.421*
H55B	0.1753	0.3134	−0.0057	0.421*
H55C	0.1467	0.3400	0.0412	0.421*
C56	0.1529 (5)	0.4517 (5)	0.0023 (2)	0.220 (3)
H56A	0.1877	0.4664	−0.0241	0.265*
H56B	0.1758	0.4980	0.0234	0.265*
C57	0.0311 (5)	0.4582 (4)	−0.0047 (3)	0.221 (4)
H57A	0.0165	0.4437	−0.0345	0.265*
H57B	0.0003	0.4074	0.0116	0.265*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.03380 (9)	0.04284 (10)	0.03775 (9)	−0.00153 (7)	0.00029 (6)	−0.00164 (7)
S1	0.0898 (6)	0.0880 (5)	0.0879 (6)	0.0087 (5)	0.0177 (5)	0.0037 (5)
P1	0.0401 (3)	0.0506 (3)	0.0378 (3)	−0.0059 (2)	0.0005 (2)	0.0001 (2)
P3	0.0354 (3)	0.0529 (3)	0.0476 (3)	−0.0014 (2)	0.0040 (2)	−0.0047 (3)
P2	0.0459 (3)	0.0482 (3)	0.0414 (3)	−0.0009 (2)	0.0010 (2)	0.0032 (2)
O1	0.0542 (10)	0.0624 (10)	0.0944 (13)	−0.0030 (8)	−0.0271 (9)	−0.0110 (10)
O2	0.193 (3)	0.0650 (16)	0.145 (2)	0.0284 (18)	0.019 (2)	0.0046 (16)
O3	0.173 (3)	0.112 (2)	0.220 (4)	0.076 (2)	−0.017 (3)	−0.022 (2)
O4	0.1203 (19)	0.1035 (18)	0.144 (2)	0.0192 (15)	0.0099 (16)	0.0336 (16)
O5	0.0866 (15)	0.135 (2)	0.135 (2)	−0.0087 (15)	0.0315 (14)	0.0224 (16)
O6	0.186 (3)	0.153 (2)	0.111 (2)	−0.027 (2)	0.0091 (19)	−0.0592 (18)
F1	0.154 (2)	0.170 (2)	0.178 (3)	−0.0203 (18)	0.0109 (19)	−0.098 (2)
F2	0.143 (2)	0.1191 (17)	0.236 (3)	0.0479 (15)	0.049 (2)	0.0631 (19)
F3	0.0921 (13)	0.1338 (17)	0.165 (2)	−0.0059 (12)	0.0491 (13)	0.0272 (15)
N1	0.120 (3)	0.079 (2)	0.0850 (19)	0.0314 (19)	0.0008 (18)	0.0077 (16)
C1	0.0426 (11)	0.0408 (11)	0.0448 (12)	−0.0048 (9)	−0.0013 (9)	0.0020 (9)
C2	0.0447 (12)	0.0530 (13)	0.0482 (12)	−0.0034 (10)	−0.0035 (10)	0.0043 (10)
C3	0.0539 (13)	0.0559 (14)	0.0472 (13)	0.0003 (11)	−0.0010 (10)	0.0044 (11)
C4	0.0569 (15)	0.0557 (16)	0.096 (2)	0.0003 (12)	−0.0026 (14)	−0.0078 (14)
C5	0.089 (2)	0.0500 (16)	0.099 (2)	0.0038 (15)	0.0033 (17)	−0.0065 (14)
C6	0.099 (2)	0.0605 (17)	0.0601 (16)	0.0193 (16)	0.0048 (15)	0.0053 (13)
C7	0.084 (2)	0.088 (2)	0.0758 (19)	0.0364 (18)	−0.0124 (16)	0.0035 (16)
C8	0.0663 (17)	0.0726 (18)	0.0681 (17)	0.0130 (13)	−0.0174 (13)	−0.0053 (13)
C9	0.0360 (10)	0.0371 (11)	0.0462 (12)	−0.0018 (8)	−0.0006 (9)	−0.0015 (9)
C10	0.0427 (12)	0.0605 (14)	0.0470 (13)	−0.0016 (10)	−0.0025 (10)	−0.0043 (10)
C11	0.0347 (12)	0.0830 (17)	0.0642 (16)	0.0008 (11)	−0.0079 (11)	−0.0086 (13)
C12	0.0335 (12)	0.0918 (19)	0.0674 (17)	−0.0053 (12)	0.0092 (11)	−0.0139 (14)
C13	0.0476 (13)	0.0662 (15)	0.0500 (13)	−0.0069 (11)	0.0083 (11)	−0.0080 (11)
C14	0.0360 (11)	0.0476 (12)	0.0435 (12)	−0.0046 (9)	0.0004 (9)	−0.0022 (9)
C15	0.0489 (12)	0.0590 (14)	0.0394 (12)	−0.0133 (11)	0.0069 (10)	−0.0066 (10)
C16	0.0681 (16)	0.0558 (15)	0.0622 (15)	−0.0101 (12)	0.0007 (12)	−0.0043 (12)
C17	0.113 (3)	0.0540 (17)	0.086 (2)	−0.0182 (16)	0.0076 (19)	−0.0043 (14)
C18	0.092 (2)	0.083 (2)	0.088 (2)	−0.0443 (18)	0.0201 (18)	−0.0323 (18)
C19	0.0768 (19)	0.097 (2)	0.0630 (17)	−0.0370 (17)	0.0086 (14)	−0.0254 (16)
C20	0.0581 (14)	0.0802 (17)	0.0471 (13)	−0.0148 (13)	0.0009 (11)	−0.0107 (12)
C21	0.0491 (13)	0.0673 (15)	0.0473 (13)	−0.0062 (12)	0.0043 (10)	0.0060 (12)
C22	0.0755 (18)	0.091 (2)	0.0469 (15)	−0.0106 (15)	0.0085 (13)	−0.0012 (13)
C23	0.0714 (18)	0.123 (3)	0.0512 (16)	−0.0050 (18)	0.0115 (13)	0.0022 (17)
C24	0.114 (3)	0.154 (4)	0.067 (2)	0.022 (3)	0.0348 (19)	0.042 (2)
C25	0.161 (4)	0.100 (3)	0.105 (3)	0.024 (3)	0.047 (3)	0.047 (2)
C26	0.150 (3)	0.088 (2)	0.090 (2)	0.019 (2)	0.061 (2)	0.0298 (18)
C27	0.0638 (15)	0.0481 (13)	0.0483 (13)	0.0064 (11)	0.0064 (11)	0.0051 (10)
C28	0.0780 (18)	0.0604 (16)	0.0767 (18)	−0.0021 (14)	0.0118 (14)	−0.0049 (14)
C29	0.111 (3)	0.0569 (18)	0.090 (2)	−0.0035 (18)	0.029 (2)	−0.0093 (16)
C30	0.145 (3)	0.069 (2)	0.076 (2)	0.039 (2)	0.041 (2)	0.0141 (17)
C31	0.138 (3)	0.115 (3)	0.084 (2)	0.073 (3)	−0.012 (2)	0.006 (2)
C32	0.104 (2)	0.0723 (18)	0.0711 (18)	0.0271 (17)	−0.0163 (17)	−0.0026 (14)
C33	0.0479 (12)	0.0562 (14)	0.0450 (12)	0.0088 (11)	−0.0031 (10)	−0.0020 (10)
C34	0.0757 (18)	0.0842 (19)	0.0491 (15)	0.0040 (14)	−0.0061 (13)	0.0033 (13)
C35	0.094 (2)	0.111 (3)	0.0451 (15)	0.014 (2)	−0.0128 (14)	−0.0116 (16)
C36	0.092 (2)	0.097 (2)	0.075 (2)	0.0012 (19)	−0.0113 (17)	−0.0382 (18)
C37	0.091 (2)	0.0646 (17)	0.077 (2)	−0.0046 (15)	0.0014 (16)	−0.0201 (15)
C38	0.0625 (15)	0.0575 (15)	0.0546 (14)	0.0037 (12)	0.0040 (11)	−0.0075 (12)
C39	0.0560 (14)	0.0681 (16)	0.0477 (13)	−0.0055 (12)	0.0069 (11)	0.0069 (11)
C40	0.0454 (13)	0.0728 (16)	0.0492 (13)	−0.0041 (11)	0.0100 (10)	−0.0038 (11)
C41	0.0444 (12)	0.0579 (14)	0.0522 (13)	0.0032 (11)	0.0103 (10)	−0.0022 (11)
C42	0.0787 (18)	0.0628 (17)	0.0718 (18)	−0.0018 (14)	−0.0072 (14)	−0.0117 (13)
C43	0.115 (3)	0.0577 (17)	0.082 (2)	0.0130 (17)	0.0013 (18)	−0.0129 (14)
C44	0.091 (2)	0.083 (2)	0.108 (3)	0.0334 (19)	0.018 (2)	0.0008 (19)
C45	0.0572 (18)	0.085 (2)	0.141 (3)	0.0117 (16)	0.0014 (18)	0.010 (2)
C46	0.0510 (15)	0.0648 (17)	0.104 (2)	0.0061 (13)	−0.0028 (14)	−0.0014 (15)
C47	0.0409 (12)	0.0489 (12)	0.0554 (13)	−0.0004 (10)	0.0021 (10)	−0.0018 (10)
C48	0.0484 (14)	0.0686 (17)	0.0848 (18)	−0.0083 (12)	0.0186 (13)	−0.0168 (14)
C49	0.0475 (14)	0.0739 (18)	0.099 (2)	−0.0160 (13)	0.0126 (14)	0.0011 (16)
C50	0.0646 (16)	0.0532 (14)	0.0797 (18)	−0.0089 (13)	−0.0098 (14)	−0.0012 (13)
C51	0.0692 (17)	0.0595 (16)	0.0702 (17)	−0.0003 (13)	0.0050 (14)	−0.0128 (13)
C52	0.0503 (13)	0.0614 (15)	0.0548 (14)	−0.0054 (11)	0.0053 (11)	−0.0049 (11)
C53	0.095 (2)	0.085 (2)	0.124 (3)	−0.002 (2)	0.023 (2)	0.008 (2)
C54A	0.122 (9)	0.263 (15)	0.195 (13)	−0.032 (9)	−0.013 (8)	0.081 (13)
Cl1A	0.159 (3)	0.172 (3)	0.267 (4)	−0.043 (2)	−0.016 (3)	0.060 (3)
Cl2A	0.207 (4)	0.462 (9)	0.195 (4)	0.047 (6)	0.012 (3)	0.067 (5)
C55	0.230 (9)	0.196 (8)	0.416 (15)	0.034 (6)	0.002 (9)	−0.029 (8)
C56	0.175 (6)	0.245 (8)	0.241 (8)	−0.032 (6)	−0.006 (5)	−0.001 (6)
C57	0.217 (10)	0.264 (11)	0.179 (6)	−0.084 (8)	−0.020 (6)	0.001 (8)

Geometric parameters (Å, º) top

Pd1—C9	2.0783 (19)	C27—C28	1.384 (3)
Pd1—C1	2.1711 (19)	C28—C29	1.378 (4)
Pd1—P2	2.2783 (6)	C28—H28	0.9300
Pd1—P3	2.3554 (6)	C29—C30	1.351 (4)
S1—O4	1.413 (2)	C29—H29	0.9300
S1—O5	1.414 (2)	C30—C31	1.348 (5)
S1—O6	1.466 (3)	C30—H30	0.9300
S1—C53	1.777 (4)	C31—C32	1.389 (4)
P1—C1	1.768 (2)	C31—H31	0.9300
P1—C14	1.783 (2)	C32—H32	0.9300
P1—C21	1.797 (2)	C33—C38	1.379 (3)
P1—C15	1.800 (2)	C33—C34	1.402 (3)
P3—C41	1.818 (2)	C34—C35	1.367 (4)
P3—C47	1.819 (2)	C34—H34	0.9300
P3—C40	1.834 (2)	C35—C36	1.356 (4)
P2—C33	1.814 (2)	C35—H35	0.9300
P2—C27	1.817 (2)	C36—C37	1.352 (4)
P2—C39	1.834 (2)	C36—H36	0.9300
O1—C2	1.218 (2)	C37—C38	1.378 (3)
O2—N1	1.182 (4)	C37—H37	0.9300
O3—N1	1.159 (4)	C38—H38	0.9300
F1—C53	1.346 (4)	C39—C40	1.517 (3)
F2—C53	1.332 (4)	C39—H39A	0.9700
F3—C53	1.324 (4)	C39—H39B	0.9700
N1—C6	1.512 (4)	C40—H40A	0.9700
C1—C2	1.471 (3)	C40—H40B	0.9700
C1—H1	0.9800	C41—C46	1.378 (3)
C2—C3	1.504 (3)	C41—C42	1.381 (3)
C3—C4	1.383 (3)	C42—C43	1.397 (4)
C3—C8	1.397 (3)	C42—H42	0.9300
C4—C5	1.392 (3)	C43—C44	1.358 (4)
C4—H4	0.9300	C43—H43	0.9300
C5—C6	1.334 (4)	C44—C45	1.376 (4)
C5—H5	0.9300	C44—H44	0.9300
C6—C7	1.361 (4)	C45—C46	1.377 (4)
C7—C8	1.375 (4)	C45—H45	0.9300
C7—H7	0.9300	C46—H46	0.9300
C8—H8	0.9300	C47—C52	1.381 (3)
C9—C10	1.397 (3)	C47—C48	1.390 (3)
C9—C14	1.405 (3)	C48—C49	1.368 (3)
C10—C11	1.378 (3)	C48—H48	0.9300
C10—H10	0.9300	C49—C50	1.383 (4)
C11—C12	1.363 (3)	C49—H49	0.9300
C11—H11	0.9300	C50—C51	1.352 (3)
C12—C13	1.380 (3)	C50—H50	0.9300
C12—H12	0.9300	C51—C52	1.378 (3)
C13—C14	1.378 (3)	C51—H51	0.9300
C13—H13	0.9300	C52—H52	0.9300
C15—C16	1.379 (3)	C54A—Cl1A	1.726 (8)
C15—C20	1.389 (3)	C54A—Cl2A	1.730 (8)
C16—C17	1.394 (3)	C54A—H54A	0.9700
C16—H16	0.9300	C54A—H54B	0.9700
C17—C18	1.370 (4)	C54B—Cl2B	1.746 (9)
C17—H17	0.9300	C54B—Cl1B	1.787 (9)
C18—C19	1.361 (4)	C54B—H54C	0.9700
C18—H18	0.9300	C54B—H54D	0.9700
C19—C20	1.381 (3)	C54C—Cl2C	1.744 (10)
C19—H19	0.9300	C54C—Cl1C	1.778 (10)
C20—H20	0.9300	C54C—H54E	0.9700
C21—C26	1.352 (4)	C54C—H54F	0.9700
C21—C22	1.386 (3)	C55—C56	1.472 (6)
C22—C23	1.384 (4)	C55—H55A	0.9600
C22—H22	0.9300	C55—H55B	0.9600
C23—C24	1.310 (4)	C55—H55C	0.9600
C23—H23	0.9300	C56—C57	1.523 (7)
C24—C25	1.357 (5)	C56—H56A	0.9700
C24—H24	0.9300	C56—H56B	0.9700
C25—C26	1.401 (4)	C57—C57ⁱ	1.455 (8)
C25—H25	0.9300	C57—H57A	0.9700
C26—H26	0.9300	C57—H57B	0.9700
C27—C32	1.375 (3)

C9—Pd1—C1	83.17 (8)	C30—C29—C28	120.0 (3)
C9—Pd1—P2	92.50 (6)	C30—C29—H29	120.0
C1—Pd1—P2	175.31 (5)	C28—C29—H29	120.0
C9—Pd1—P3	175.68 (5)	C31—C30—C29	120.6 (3)
C1—Pd1—P3	100.49 (5)	C31—C30—H30	119.7
P2—Pd1—P3	83.91 (2)	C29—C30—H30	119.7
O4—S1—O5	116.71 (16)	C30—C31—C32	120.7 (3)
O4—S1—O6	112.71 (18)	C30—C31—H31	119.7
O5—S1—O6	114.10 (17)	C32—C31—H31	119.7
O4—S1—C53	104.18 (18)	C27—C32—C31	119.5 (3)
O5—S1—C53	104.67 (17)	C27—C32—H32	120.3
O6—S1—C53	102.43 (19)	C31—C32—H32	120.3
C1—P1—C14	100.26 (9)	C38—C33—C34	118.5 (2)
C1—P1—C21	114.63 (11)	C38—C33—P2	120.54 (17)
C14—P1—C21	110.91 (10)	C34—C33—P2	120.85 (19)
C1—P1—C15	116.56 (10)	C35—C34—C33	119.5 (3)
C14—P1—C15	108.63 (10)	C35—C34—H34	120.2
C21—P1—C15	105.72 (10)	C33—C34—H34	120.2
C41—P3—C47	106.47 (10)	C36—C35—C34	120.7 (3)
C41—P3—C40	103.43 (10)	C36—C35—H35	119.6
C47—P3—C40	101.05 (10)	C34—C35—H35	119.6
C41—P3—Pd1	123.64 (7)	C37—C36—C35	120.8 (3)
C47—P3—Pd1	114.05 (7)	C37—C36—H36	119.6
C40—P3—Pd1	105.28 (7)	C35—C36—H36	119.6
C33—P2—C27	108.75 (10)	C36—C37—C38	119.9 (3)
C33—P2—C39	102.42 (11)	C36—C37—H37	120.0
C27—P2—C39	104.28 (11)	C38—C37—H37	120.0
C33—P2—Pd1	113.60 (7)	C37—C38—C33	120.5 (2)
C27—P2—Pd1	117.51 (7)	C37—C38—H38	119.8
C39—P2—Pd1	108.79 (8)	C33—C38—H38	119.8
O3—N1—O2	126.6 (4)	C40—C39—P2	107.48 (15)
O3—N1—C6	117.0 (4)	C40—C39—H39A	110.2
O2—N1—C6	116.4 (3)	P2—C39—H39A	110.2
C2—C1—P1	118.04 (15)	C40—C39—H39B	110.2
C2—C1—Pd1	119.69 (14)	P2—C39—H39B	110.2
P1—C1—Pd1	99.62 (9)	H39A—C39—H39B	108.5
C2—C1—H1	106.1	C39—C40—P3	107.53 (15)
P1—C1—H1	106.1	C39—C40—H40A	110.2
Pd1—C1—H1	106.1	P3—C40—H40A	110.2
O1—C2—C1	122.1 (2)	C39—C40—H40B	110.2
O1—C2—C3	119.31 (19)	P3—C40—H40B	110.2
C1—C2—C3	118.59 (19)	H40A—C40—H40B	108.5
C4—C3—C8	118.1 (2)	C46—C41—C42	118.7 (2)
C4—C3—C2	124.1 (2)	C46—C41—P3	123.39 (19)
C8—C3—C2	117.8 (2)	C42—C41—P3	117.94 (18)
C3—C4—C5	120.6 (2)	C41—C42—C43	120.0 (3)
C3—C4—H4	119.7	C41—C42—H42	120.0
C5—C4—H4	119.7	C43—C42—H42	120.0
C6—C5—C4	119.0 (3)	C44—C43—C42	120.0 (3)
C6—C5—H5	120.5	C44—C43—H43	120.0
C4—C5—H5	120.5	C42—C43—H43	120.0
C5—C6—C7	122.8 (3)	C43—C44—C45	120.7 (3)
C5—C6—N1	118.5 (3)	C43—C44—H44	119.6
C7—C6—N1	118.7 (3)	C45—C44—H44	119.6
C6—C7—C8	119.0 (3)	C44—C45—C46	119.1 (3)
C6—C7—H7	120.5	C44—C45—H45	120.4
C8—C7—H7	120.5	C46—C45—H45	120.4
C7—C8—C3	120.5 (3)	C45—C46—C41	121.5 (3)
C7—C8—H8	119.7	C45—C46—H46	119.3
C3—C8—H8	119.7	C41—C46—H46	119.3
C10—C9—C14	115.00 (18)	C52—C47—C48	117.5 (2)
C10—C9—Pd1	128.35 (16)	C52—C47—P3	120.37 (16)
C14—C9—Pd1	116.65 (14)	C48—C47—P3	121.90 (17)
C11—C10—C9	121.6 (2)	C49—C48—C47	121.1 (2)
C11—C10—H10	119.2	C49—C48—H48	119.4
C9—C10—H10	119.2	C47—C48—H48	119.4
C12—C11—C10	121.6 (2)	C48—C49—C50	120.5 (2)
C12—C11—H11	119.2	C48—C49—H49	119.8
C10—C11—H11	119.2	C50—C49—H49	119.8
C11—C12—C13	119.3 (2)	C51—C50—C49	118.7 (2)
C11—C12—H12	120.4	C51—C50—H50	120.7
C13—C12—H12	120.4	C49—C50—H50	120.7
C14—C13—C12	119.0 (2)	C50—C51—C52	121.5 (2)
C14—C13—H13	120.5	C50—C51—H51	119.2
C12—C13—H13	120.5	C52—C51—H51	119.2
C13—C14—C9	123.56 (19)	C51—C52—C47	120.6 (2)
C13—C14—P1	124.16 (16)	C51—C52—H52	119.7
C9—C14—P1	112.28 (14)	C47—C52—H52	119.7
C16—C15—C20	119.9 (2)	F3—C53—F2	105.1 (3)
C16—C15—P1	120.01 (17)	F3—C53—F1	109.0 (3)
C20—C15—P1	120.12 (19)	F2—C53—F1	109.5 (3)
C15—C16—C17	119.1 (2)	F3—C53—S1	112.8 (3)
C15—C16—H16	120.4	F2—C53—S1	110.9 (3)
C17—C16—H16	120.4	F1—C53—S1	109.4 (3)
C18—C17—C16	120.3 (3)	Cl1A—C54A—Cl2A	106.1 (6)
C18—C17—H17	119.8	Cl1A—C54A—H54A	110.5
C16—C17—H17	119.8	Cl2A—C54A—H54A	110.5
C19—C18—C17	120.6 (3)	Cl1A—C54A—H54B	110.5
C19—C18—H18	119.7	Cl2A—C54A—H54B	110.5
C17—C18—H18	119.7	H54A—C54A—H54B	108.7
C18—C19—C20	120.0 (3)	Cl2B—C54B—Cl1B	106.2 (8)
C18—C19—H19	120.0	Cl2B—C54B—H54C	110.5
C20—C19—H19	120.0	Cl1B—C54B—H54C	110.5
C19—C20—C15	120.1 (3)	Cl2B—C54B—H54D	110.5
C19—C20—H20	120.0	Cl1B—C54B—H54D	110.5
C15—C20—H20	120.0	H54C—C54B—H54D	108.7
C26—C21—C22	118.4 (2)	Cl2C—C54C—Cl1C	96.1 (7)
C26—C21—P1	120.5 (2)	Cl2C—C54C—H54E	112.5
C22—C21—P1	121.1 (2)	Cl1C—C54C—H54E	112.5
C23—C22—C21	120.6 (3)	Cl2C—C54C—H54F	112.5
C23—C22—H22	119.7	Cl1C—C54C—H54F	112.5
C21—C22—H22	119.7	H54E—C54C—H54F	110.1
C24—C23—C22	120.6 (3)	C56—C55—H55A	109.5
C24—C23—H23	119.7	C56—C55—H55B	109.5
C22—C23—H23	119.7	H55A—C55—H55B	109.5
C23—C24—C25	120.1 (3)	C56—C55—H55C	109.5
C23—C24—H24	119.9	H55A—C55—H55C	109.5
C25—C24—H24	119.9	H55B—C55—H55C	109.5
C24—C25—C26	120.6 (3)	C55—C56—C57	112.2 (6)
C24—C25—H25	119.7	C55—C56—H56A	109.2
C26—C25—H25	119.7	C57—C56—H56A	109.2
C21—C26—C25	119.3 (3)	C55—C56—H56B	109.2
C21—C26—H26	120.3	C57—C56—H56B	109.2
C25—C26—H26	120.3	H56A—C56—H56B	107.9
C32—C27—C28	118.8 (2)	C57ⁱ—C57—C56	123.4 (9)
C32—C27—P2	123.8 (2)	C57ⁱ—C57—H57A	106.5
C28—C27—P2	117.34 (19)	C56—C57—H57A	106.5
C29—C28—C27	120.4 (3)	C57ⁱ—C57—H57B	106.5
C29—C28—H28	119.8	C56—C57—H57B	106.5
C27—C28—H28	119.8	H57A—C57—H57B	106.5

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O1ⁱⁱ	0.93	2.54	3.284 (3)	138
C30—H30···O6ⁱⁱⁱ	0.93	2.55	3.372 (4)	148
C39—H39B···O6^iv	0.97	2.59	3.309 (4)	131

Symmetry codes: (ii) −x+1, −y, −z; (iii) x, y−1, z; (iv) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Pd(C₂₆H₁₉NO₃P)(C₂₆H₂₄P₂)]CF₃O₃S·CH₂Cl₂·0.5C₆H₁₄
M_r	1206.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	12.4063 (7), 14.2445 (8), 31.3633 (17)
β (°)	91.6675 (9)
V (Å³)	5540.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.19 × 0.16 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.872, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	62924, 10529, 8106
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.076, 1.04
No. of reflections	10529
No. of parameters	691
No. of restraints	14
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.38

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SIR97 (Altomare et al., 1999), ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL97 (Keller, 1997), SHELXL97 (Sheldrick, 2008) and PARST95 (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O1ⁱ	0.93	2.54	3.284 (3)	138
C30—H30···O6ⁱⁱ	0.93	2.55	3.372 (4)	148
C39—H39B···O6ⁱⁱⁱ	0.97	2.59	3.309 (4)	131

Symmetry codes: (i) −x+1, −y, −z; (ii) x, y−1, z; (iii) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

Financial support from the Universitá degli Studi di Parma is gratefully acknowledged.

References

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