trans-Dichloridobis{dicyclo­hex­yl[4-(dimethyl­amino)­phen­yl]phosphane-κP}platinum(II) dichloro­methane disolvate

Davis, W.L.; Meijboom, R.

doi:10.1107/S1600536812048465

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1561

doi:10.1107/S1600536812048465

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trans-Dichloridobis{dicyclohexyl[4-(dimethylamino)phenyl]phosphane-κP}platinum(II) dichloromethane disolvate

Wade L. Davis ^a and Reinout Meijboom ^a ^*

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

(Received 6 November 2012; accepted 26 November 2012; online 30 November 2012)

In the title complex, trans-[PtCl₂{P(C₆H₁₁)₂(4-Me₂NC₆H₄)}₂]·2CH₂Cl₂, the Pt^II atom is located on an inversion centre, resulting in a trans-square-planar geometry. Important geometric parameters are the Pt—P and Pt—Cl bond lengths of 2.3258 (6) and 2.3106 (6) Å, respectively, and the P—Pt—Cl angles of 89.64 (2) and 90.36 (2)°. The effective cone angle for the dicyclohexyl[4-(dimethylamino)phenyl]phosphane unit was calculated to be 164°. The compound crystallizes with two dichloromethane solvent molecules; one of which is severely disordered and was treated using the SQUEEZE routine in PLATON [Spek (2009 ). Acta Cryst. D65, 148–155].

Related literature

For a review on related compounds, see: Spessard & Miessler (1996 ). For related compounds, see: Johansson et al. (2002 ). For similar R-P₂PtCl₂ compounds, see: Lutz et al. (2005 ). For the synthesis of starting materials, see: Drew & Doyle (1990 ). For use of the SQUEEZE routine in PLATON to remove the contribution of disordered solvents, see: Spek (2009). For background to cone angles, see: Tolman (1977 ); Otto (2001 ).

Experimental

Crystal data

[PtCl₂(C₂₀H₃₂NP)₂]·2CH₂Cl₂
M_r = 1070.70
Monoclinic, C 2/c
a = 19.4146 (9) Å
b = 13.1517 (6) Å
c = 19.3459 (9) Å
β = 94.660 (2)°
V = 4923.4 (4) Å³
Z = 4
Cu Kα radiation
μ = 9.16 mm⁻¹
T = 100 K
0.26 × 0.24 × 0.16 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.199, T_max = 0.322
56178 measured reflections
4239 independent reflections
4069 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.067
S = 1.08
4239 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 1.72 e Å⁻³
Δρ_min = −1.15 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); 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: publCIF (Westrip, 2010 ) and WinGX (Farrugia, 2012 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812048465/su2526sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812048465/su2526Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812048465/su2526Isup3.cdx

checkCIF report

Comment top

Transition metal complexes containing phosphine, arsine and stibine ligands are widely being investigated in various fields of organometallic chemistry (Spessard & Miessler, 1996). [PtCl₂(L)₂] (L = tertiary phosphine, arsine or stibine) complexes can conveniently be prepared by the substitution of 1,5-cyclooctadiene (COD) from [PtCl₂(COD)]. As part of a systematic investigation involving complexes with the general formula cis/trans-[MX₂(L)₂] (M = Pt or Pd; X = halogen, Me, Ph; L = Group 15 donor ligand), we have synthesized the title compound and report herein on its crystal structure.

In the title compound, Fig. 1, the Pt atom is located on an inversion center with each pair of equivalent ligands in a mutually trans orientation. The geometry is, therefore, square planar and the Pt atom is not elevated out of the coordinating atom plane. All the bond angles in the coordination polyhedron are close to their ideal value of 90°, with P1—Pt1—Cl1 = 90.4 (2)° and P1—Pt1—Clⁱ = 89.6 (2)°. As required by the crystallographic symmetry, the P1—Pt1—Pⁱ and Cl1—Pt1—Clⁱ angles are both 180° [symmetry code: (i) -x+3/2, -y+1/2, -z.].

To describe the steric demand of the phosphane ligands the Tolman cone angle (Tolman, 1977) is still the most commonly used model. Applying this model to the geometry obtained from the title compound (and adjusting the Pt—P bond distance to 2.28 Å) we calculated an effective cone angle (Otto, 2001) of 164°.

The title compound compares well with other closely related Pt^II complexes reported in the literature containing two chloride and two tertiary phosphine ligands in a trans geometry (Lutz et al., 2005). The Pt—P and Pt—Cl bond distances of 2.326 (6) and 2.311 (6) Å, respectively for the title compound, fit well into the typical range for complexes of this kind. The title compound crystallizes as a solvated complex which is common for these type of Pt^II complexes (Johansson et al., 2002).

The title compound crystallizes with two molecules of dichloromethane. One of these molecules was initially modelled as a severely disordered molecule. We subsequently removed the disordered dichloromethane molecule by applying the SQUEEZE routine as found in PLATON (Spek, 2009).

Related literature top

For a review on related compounds, see: Spessard & Miessler (1996). For related compounds, see: Johansson et al. (2002). For similar R-P₂PtCl₂ compounds, see: Lutz et al. (2005). For the synthesis of starting materials, see: Drew & Doyle (1990). For use of the SQUEEZE routine in PLATON to remove the contribution of disordered solvents , see: Spek (2009). For background to cone angles, see: Tolman (1977); Otto (2001).

Experimental top

Dichloro(1,5-cyclooctadiene)platinum(II), [PtCl₂(COD)], was prepared according to the literature procedure (Drew & Doyle, 1990). A solution of dicyclohexyl-[4-(N,N-dimethylamino)phenyl]phosphine (63.5 mg, 0.2 mmol) in dichloromethane (2 cm³) was added to a solution of [PtCl₂(COD)] (37.4 mg, 0.1 mmol) in dichloromethane (3 cm³). Slow evaporation of the solvent gave colourless crystals of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); 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: publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).

Figures top

Fig. 1. The molecular structure of the title complex, showing the atom numbering and the ordered dichloromethane solvent molecule. The displacement ellipsoids are drawn at the 50% probability level [Symmetry code: (i) -x+3/2, -y+1/2, -z].

trans-Dichloridobis{dicyclohexyl[4-(dimethylamino)phenyl]phosphane-κP}platinum(II) dichloromethane disolvate top

Crystal data top

[PtCl₂(C₂₀H₃₂NP)₂]·2CH₂Cl₂	F(000) = 2176
M_r = 1070.70	D_x = 1.445 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 9651 reflections
a = 19.4146 (9) Å	θ = 4.1–65.7°
b = 13.1517 (6) Å	µ = 9.16 mm⁻¹
c = 19.3459 (9) Å	T = 100 K
β = 94.660 (2)°	Cuboid, colourless
V = 4923.4 (4) Å³	0.26 × 0.24 × 0.16 mm
Z = 4

Data collection top

Bruker APEX DUO 4K CCD diffractometer	4239 independent reflections
Radiation source: Incoatec IµS microfocus X-ray source	4069 reflections with I > 2σ(I)
Incoatec Quazar Multilayer Mirror monochromator	R_int = 0.045
Detector resolution: 8.4 pixels mm^-1	θ_max = 66.2°, θ_min = 4.1°
ϕ and ω scans	h = −21→22
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −14→15
T_min = 0.199, T_max = 0.322	l = −22→21
56178 measured reflections

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0406P)² + 10.7442P] where P = (F_o² + 2F_c²)/3
4239 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 1.72 e Å⁻³
0 restraints	Δρ_min = −1.15 e Å⁻³

Crystal data top

[PtCl₂(C₂₀H₃₂NP)₂]·2CH₂Cl₂	V = 4923.4 (4) Å³
M_r = 1070.70	Z = 4
Monoclinic, C2/c	Cu Kα radiation
a = 19.4146 (9) Å	µ = 9.16 mm⁻¹
b = 13.1517 (6) Å	T = 100 K
c = 19.3459 (9) Å	0.26 × 0.24 × 0.16 mm
β = 94.660 (2)°

Data collection top

Bruker APEX DUO 4K CCD diffractometer	4239 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4069 reflections with I > 2σ(I)
T_min = 0.199, T_max = 0.322	R_int = 0.045
56178 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0406P)² + 10.7442P] where P = (F_o² + 2F_c²)/3
4239 reflections	Δρ_max = 1.72 e Å⁻³
244 parameters	Δρ_min = −1.15 e Å⁻³

Special details top

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. Highly disordered solvate molecule is observed, resulting in residual electron density around the C4 atom. Different disordered models, however, resulted in unstable refinement cycles. Placement of H atoms on C4 also resulted in unstable refinement. This procedure resulted in unsatisfactory refinements and the molecule was removed by applying the SQUEEZE routine as found in PLATON (Spek, 2003).

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

	x	y	z	U_iso*/U_eq
Pt1	0.75	0.25	0	0.01460 (8)
Cl1	0.85498 (3)	0.19559 (5)	0.05181 (3)	0.02286 (14)
P1	0.69307 (3)	0.17595 (4)	0.08851 (3)	0.01619 (13)
C31	0.74703 (13)	0.15612 (19)	0.17086 (12)	0.0202 (5)
H131	0.7901	0.1206	0.1591	0.024*
C34	0.78157 (15)	0.1765 (2)	0.32170 (14)	0.0321 (6)
H13A	0.7403	0.2114	0.337	0.039*
H13B	0.8142	0.1651	0.363	0.039*
C36	0.76895 (17)	0.25841 (19)	0.20359 (17)	0.0241 (7)
H13C	0.7939	0.2985	0.1702	0.029*
H13D	0.7273	0.2972	0.214	0.029*
C11	0.61712 (16)	0.24227 (17)	0.11403 (15)	0.0179 (6)
C15	0.50367 (17)	0.24432 (17)	0.15855 (16)	0.0197 (6)
H115	0.4654	0.2075	0.1734	0.024*
C26	0.72650 (14)	−0.0195 (2)	0.04868 (15)	0.0269 (6)
H12A	0.7522	0.0105	0.0115	0.032*
H12B	0.758	−0.0229	0.0915	0.032*
C16	0.56012 (13)	0.19181 (19)	0.13759 (12)	0.0193 (5)
H116	0.5602	0.1196	0.1393	0.023*
C13	0.55973 (13)	0.40207 (18)	0.13530 (12)	0.0192 (5)
H113	0.5605	0.4743	0.1347	0.023*
C35	0.81549 (19)	0.2434 (2)	0.27030 (18)	0.0302 (8)
H13E	0.8595	0.2119	0.259	0.036*
H13F	0.8263	0.3104	0.2918	0.036*
C25	0.70229 (16)	−0.1267 (2)	0.02768 (17)	0.0352 (7)
H12C	0.7427	−0.168	0.017	0.042*
H12D	0.6812	−0.1591	0.067	0.042*
C24	0.65002 (17)	−0.1253 (2)	−0.03515 (16)	0.0365 (7)
H12E	0.6335	−0.1954	−0.0453	0.044*
H12F	0.6726	−0.1003	−0.076	0.044*
C32	0.71270 (14)	0.0884 (2)	0.22298 (13)	0.0246 (5)
H13G	0.6687	0.1198	0.2345	0.029*
H13H	0.702	0.0211	0.2018	0.029*
C12	0.61541 (13)	0.34844 (19)	0.11366 (12)	0.0188 (5)
H112	0.6535	0.3848	0.0981	0.023*
Cl2	0.03909 (4)	0.22618 (7)	0.10388 (4)	0.04094 (18)
Cl3	0.09563 (4)	0.09162 (6)	0.00234 (4)	0.03576 (17)
N1	0.44579 (11)	0.40351 (16)	0.17961 (11)	0.0214 (4)
C14	0.50191 (13)	0.35131 (19)	0.15818 (12)	0.0192 (5)
C21	0.66396 (13)	0.04799 (19)	0.06127 (13)	0.0204 (5)
H121	0.6398	0.0172	0.0999	0.025*
C2	0.38221 (13)	0.3494 (2)	0.18892 (14)	0.0250 (5)
H2A	0.366	0.3156	0.1455	0.038*
H2B	0.347	0.3976	0.202	0.038*
H2C	0.3906	0.2985	0.2256	0.038*
C3	0.02418 (15)	0.1670 (2)	0.02159 (15)	0.0327 (6)
H3A	−0.0176	0.1237	0.0212	0.039*
H3B	0.0157	0.2198	−0.0146	0.039*
C33	0.76035 (15)	0.0747 (2)	0.28947 (13)	0.0305 (6)
H13I	0.7362	0.0341	0.3232	0.037*
H13J	0.8022	0.0367	0.2786	0.037*
C1	0.44126 (15)	0.5125 (2)	0.17206 (16)	0.0310 (6)
H1A	0.4849	0.5435	0.1903	0.047*
H1B	0.4035	0.5382	0.1979	0.047*
H1C	0.4323	0.5298	0.1229	0.047*
C22	0.61287 (14)	0.0505 (2)	−0.00345 (13)	0.0258 (6)
H12G	0.5725	0.093	0.0056	0.031*
H12H	0.6354	0.0812	−0.0426	0.031*
C23	0.58883 (16)	−0.0575 (2)	−0.02278 (16)	0.0338 (7)
H12I	0.5635	−0.0862	0.0151	0.041*
H12J	0.5568	−0.0552	−0.0653	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.01470 (11)	0.01799 (11)	0.01167 (10)	0.00316 (4)	0.00452 (6)	0.00001 (4)
Cl1	0.0180 (3)	0.0343 (3)	0.0169 (3)	0.0085 (2)	0.0052 (2)	0.0057 (2)
P1	0.0175 (3)	0.0184 (3)	0.0133 (3)	0.0028 (2)	0.0056 (2)	−0.0004 (2)
C31	0.0228 (12)	0.0243 (12)	0.0139 (11)	0.0056 (10)	0.0048 (9)	0.0003 (10)
C34	0.0322 (15)	0.0480 (17)	0.0161 (13)	0.0121 (13)	0.0018 (11)	−0.0015 (12)
C36	0.0247 (16)	0.0287 (16)	0.0191 (16)	0.0048 (10)	0.0019 (13)	−0.0010 (9)
C11	0.0196 (15)	0.0213 (14)	0.0131 (14)	0.0027 (9)	0.0040 (11)	−0.0005 (8)
C15	0.0199 (15)	0.0240 (15)	0.0159 (15)	0.0004 (9)	0.0051 (12)	0.0021 (8)
C26	0.0276 (14)	0.0200 (13)	0.0343 (15)	0.0039 (11)	0.0102 (11)	−0.0048 (11)
C16	0.0249 (12)	0.0176 (11)	0.0159 (11)	0.0019 (10)	0.0043 (10)	0.0015 (9)
C13	0.0228 (12)	0.0184 (12)	0.0170 (11)	0.0033 (10)	0.0056 (9)	0.0003 (9)
C35	0.0291 (18)	0.0406 (19)	0.0201 (17)	0.0048 (11)	−0.0027 (14)	−0.0042 (10)
C25	0.0375 (16)	0.0223 (14)	0.0480 (18)	0.0024 (12)	0.0176 (14)	−0.0076 (12)
C24	0.0444 (17)	0.0280 (14)	0.0400 (17)	−0.0112 (13)	0.0207 (14)	−0.0143 (13)
C32	0.0291 (14)	0.0271 (13)	0.0186 (12)	0.0059 (11)	0.0082 (11)	0.0029 (10)
C12	0.0207 (12)	0.0213 (12)	0.0147 (11)	−0.0001 (10)	0.0045 (9)	0.0010 (9)
Cl2	0.0401 (4)	0.0589 (4)	0.0238 (4)	−0.0154 (4)	0.0020 (3)	−0.0031 (3)
Cl3	0.0300 (3)	0.0473 (4)	0.0306 (4)	0.0040 (3)	0.0059 (3)	0.0100 (3)
N1	0.0204 (10)	0.0240 (11)	0.0212 (11)	0.0055 (8)	0.0099 (8)	0.0015 (8)
C14	0.0210 (12)	0.0250 (12)	0.0122 (11)	0.0037 (10)	0.0047 (9)	0.0009 (9)
C21	0.0220 (12)	0.0203 (12)	0.0202 (12)	0.0021 (10)	0.0091 (10)	−0.0022 (9)
C2	0.0189 (12)	0.0327 (14)	0.0247 (13)	0.0036 (10)	0.0085 (10)	−0.0007 (11)
C3	0.0257 (14)	0.0487 (18)	0.0236 (14)	−0.0020 (12)	0.0019 (11)	0.0012 (12)
C33	0.0356 (15)	0.0386 (16)	0.0180 (13)	0.0130 (12)	0.0078 (11)	0.0055 (11)
C1	0.0297 (14)	0.0275 (14)	0.0374 (16)	0.0076 (11)	0.0120 (12)	−0.0035 (12)
C22	0.0276 (13)	0.0290 (14)	0.0214 (13)	−0.0013 (11)	0.0057 (11)	−0.0043 (11)
C23	0.0337 (16)	0.0343 (16)	0.0342 (16)	−0.0086 (13)	0.0082 (13)	−0.0110 (13)

Geometric parameters (Å, º) top

Pt1—Cl1ⁱ	2.3106 (5)	C25—C24	1.519 (5)
Pt1—Cl1	2.3106 (6)	C25—H12C	0.99
Pt1—P1	2.3258 (6)	C25—H12D	0.99
Pt1—P1ⁱ	2.3258 (6)	C24—C23	1.520 (4)
P1—C11	1.816 (3)	C24—H12E	0.99
P1—C21	1.839 (2)	C24—H12F	0.99
P1—C31	1.853 (2)	C32—C33	1.533 (4)
C31—C36	1.532 (4)	C32—H13G	0.99
C31—C32	1.537 (4)	C32—H13H	0.99
C31—H131	1	C12—H112	0.95
C34—C35	1.517 (5)	Cl2—C3	1.775 (3)
C34—C33	1.520 (4)	Cl3—C3	1.769 (3)
C34—H13A	0.99	N1—C14	1.380 (3)
C34—H13B	0.99	N1—C1	1.443 (4)
C36—C35	1.527 (4)	N1—C2	1.448 (3)
C36—H13C	0.99	C21—C22	1.533 (4)
C36—H13D	0.99	C21—H121	1
C11—C12	1.397 (3)	C2—H2A	0.98
C11—C16	1.398 (4)	C2—H2B	0.98
C15—C16	1.384 (4)	C2—H2C	0.98
C15—C14	1.407 (3)	C3—H3A	0.99
C15—H115	0.95	C3—H3B	0.99
C26—C25	1.530 (4)	C33—H13I	0.99
C26—C21	1.539 (3)	C33—H13J	0.99
C26—H12A	0.99	C1—H1A	0.98
C26—H12B	0.99	C1—H1B	0.98
C16—H116	0.95	C1—H1C	0.98
C13—C12	1.384 (4)	C22—C23	1.532 (4)
C13—C14	1.408 (4)	C22—H12G	0.99
C13—H113	0.95	C22—H12H	0.99
C35—H13E	0.99	C23—H12I	0.99
C35—H13F	0.99	C23—H12J	0.99

Cl1ⁱ—Pt1—Cl1	180.00 (4)	C23—C24—H12E	109.4
Cl1ⁱ—Pt1—P1	89.64 (2)	C25—C24—H12F	109.4
Cl1—Pt1—P1	90.36 (2)	C23—C24—H12F	109.4
Cl1ⁱ—Pt1—P1ⁱ	90.36 (2)	H12E—C24—H12F	108
Cl1—Pt1—P1ⁱ	89.64 (2)	C33—C32—C31	110.8 (2)
P1—Pt1—P1ⁱ	180.00 (4)	C33—C32—H13G	109.5
C11—P1—C21	106.27 (11)	C31—C32—H13G	109.5
C11—P1—C31	104.40 (12)	C33—C32—H13H	109.5
C21—P1—C31	104.88 (11)	C31—C32—H13H	109.5
C11—P1—Pt1	116.36 (9)	H13G—C32—H13H	108.1
C21—P1—Pt1	109.01 (8)	C13—C12—C11	121.8 (2)
C31—P1—Pt1	115.00 (8)	C13—C12—H112	119.1
C36—C31—C32	111.0 (2)	C11—C12—H112	119.1
C36—C31—P1	110.51 (18)	C14—N1—C1	120.5 (2)
C32—C31—P1	113.61 (18)	C14—N1—C2	119.7 (2)
C36—C31—H131	107.1	C1—N1—C2	117.1 (2)
C32—C31—H131	107.1	N1—C14—C15	121.0 (2)
P1—C31—H131	107.1	N1—C14—C13	121.9 (2)
C35—C34—C33	111.1 (2)	C15—C14—C13	117.1 (2)
C35—C34—H13A	109.4	C22—C21—C26	110.4 (2)
C33—C34—H13A	109.4	C22—C21—P1	112.19 (18)
C35—C34—H13B	109.4	C26—C21—P1	110.20 (17)
C33—C34—H13B	109.4	C22—C21—H121	108
H13A—C34—H13B	108	C26—C21—H121	108
C35—C36—C31	111.2 (2)	P1—C21—H121	108
C35—C36—H13C	109.4	N1—C2—H2A	109.5
C31—C36—H13C	109.4	N1—C2—H2B	109.5
C35—C36—H13D	109.4	H2A—C2—H2B	109.5
C31—C36—H13D	109.4	N1—C2—H2C	109.5
H13C—C36—H13D	108	H2A—C2—H2C	109.5
C12—C11—C16	117.2 (2)	H2B—C2—H2C	109.5
C12—C11—P1	119.9 (2)	Cl3—C3—Cl2	111.17 (15)
C16—C11—P1	122.85 (17)	Cl3—C3—H3A	109.4
C16—C15—C14	121.1 (3)	Cl2—C3—H3A	109.4
C16—C15—H115	119.4	Cl3—C3—H3B	109.4
C14—C15—H115	119.4	Cl2—C3—H3B	109.4
C25—C26—C21	110.1 (2)	H3A—C3—H3B	108
C25—C26—H12A	109.6	C34—C33—C32	111.4 (2)
C21—C26—H12A	109.6	C34—C33—H13I	109.3
C25—C26—H12B	109.6	C32—C33—H13I	109.3
C21—C26—H12B	109.6	C34—C33—H13J	109.3
H12A—C26—H12B	108.1	C32—C33—H13J	109.3
C15—C16—C11	121.7 (2)	H13I—C33—H13J	108
C15—C16—H116	119.2	N1—C1—H1A	109.5
C11—C16—H116	119.2	N1—C1—H1B	109.5
C12—C13—C14	121.0 (2)	H1A—C1—H1B	109.5
C12—C13—H113	119.5	N1—C1—H1C	109.5
C14—C13—H113	119.5	H1A—C1—H1C	109.5
C34—C35—C36	111.7 (3)	H1B—C1—H1C	109.5
C34—C35—H13E	109.3	C23—C22—C21	110.1 (2)
C36—C35—H13E	109.3	C23—C22—H12G	109.6
C34—C35—H13F	109.3	C21—C22—H12G	109.6
C36—C35—H13F	109.3	C23—C22—H12H	109.6
H13E—C35—H13F	107.9	C21—C22—H12H	109.6
C24—C25—C26	111.9 (2)	H12G—C22—H12H	108.2
C24—C25—H12C	109.2	C24—C23—C22	110.9 (2)
C26—C25—H12C	109.2	C24—C23—H12I	109.5
C24—C25—H12D	109.2	C22—C23—H12I	109.5
C26—C25—H12D	109.2	C24—C23—H12J	109.5
H12C—C25—H12D	107.9	C22—C23—H12J	109.5
C25—C24—C23	111.2 (2)	H12I—C23—H12J	108.1
C25—C24—H12E	109.4

Cl1ⁱ—Pt1—P1—C11	−34.86 (10)	C36—C31—C32—C33	−55.2 (3)
Cl1—Pt1—P1—C11	145.14 (10)	P1—C31—C32—C33	179.56 (17)
Cl1ⁱ—Pt1—P1—C21	85.23 (9)	C14—C13—C12—C11	−0.5 (4)
Cl1—Pt1—P1—C21	−94.77 (9)	C16—C11—C12—C13	−0.3 (4)
Cl1ⁱ—Pt1—P1—C31	−157.36 (9)	P1—C11—C12—C13	−177.42 (19)
Cl1—Pt1—P1—C31	22.64 (9)	C1—N1—C14—C15	−173.3 (3)
C11—P1—C31—C36	−62.6 (2)	C2—N1—C14—C15	−12.9 (4)
C21—P1—C31—C36	−174.20 (19)	C1—N1—C14—C13	6.9 (4)
Pt1—P1—C31—C36	66.1 (2)	C2—N1—C14—C13	167.3 (2)
C11—P1—C31—C32	62.9 (2)	C16—C15—C14—N1	−179.5 (2)
C21—P1—C31—C32	−48.7 (2)	C16—C15—C14—C13	0.3 (4)
Pt1—P1—C31—C32	−168.41 (15)	C12—C13—C14—N1	−179.7 (2)
C32—C31—C36—C35	54.9 (3)	C12—C13—C14—C15	0.5 (4)
P1—C31—C36—C35	−178.1 (2)	C25—C26—C21—C22	−56.8 (3)
C21—P1—C11—C12	−157.2 (2)	C25—C26—C21—P1	178.7 (2)
C31—P1—C11—C12	92.2 (2)	C11—P1—C21—C22	64.7 (2)
Pt1—P1—C11—C12	−35.7 (3)	C31—P1—C21—C22	174.93 (17)
C21—P1—C11—C16	25.8 (3)	Pt1—P1—C21—C22	−61.43 (18)
C31—P1—C11—C16	−84.7 (3)	C11—P1—C21—C26	−171.79 (18)
Pt1—P1—C11—C16	147.4 (2)	C31—P1—C21—C26	−61.6 (2)
C14—C15—C16—C11	−1.2 (4)	Pt1—P1—C21—C26	62.07 (18)
C12—C11—C16—C15	1.2 (4)	C35—C34—C33—C32	−56.0 (3)
P1—C11—C16—C15	178.2 (2)	C31—C32—C33—C34	55.9 (3)
C33—C34—C35—C36	55.7 (3)	C26—C21—C22—C23	58.1 (3)
C31—C36—C35—C34	−55.3 (3)	P1—C21—C22—C23	−178.51 (18)
C21—C26—C25—C24	55.6 (3)	C25—C24—C23—C22	56.3 (3)
C26—C25—C24—C23	−55.5 (3)	C21—C22—C23—C24	−57.8 (3)

Symmetry code: (i) −x+3/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	[PtCl₂(C₂₀H₃₂NP)₂]·2CH₂Cl₂
M_r	1070.70
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	19.4146 (9), 13.1517 (6), 19.3459 (9)
β (°)	94.660 (2)
V (Å³)	4923.4 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	9.16
Crystal size (mm)	0.26 × 0.24 × 0.16

Data collection
Diffractometer	Bruker APEX DUO 4K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.199, 0.322
No. of measured, independent and observed [I > 2σ(I)] reflections	56178, 4239, 4069
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.593

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.067, 1.08
No. of reflections	4239
No. of parameters	244
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0406P)² + 10.7442P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.72, −1.15

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2008), SAINT and XPREP (Bruker, 2008), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).

Acknowledgements

Financial assistance from the Research Fund of the University of Johannesburg and SASOL is gratefully acknowledged. A. Muller is acknowledged for the data collection.

References

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