Dichloro­(propane-1,3-diamine-[kappa]²N,N')platinum(II), dichloro­(propane-1,3-diamine-[kappa]²N,N')­palladium(II) and [mu]-4,9-diaza­dodecane-1,12-diamine-[kappa]²N¹,N⁴:[kappa]²N⁹,N¹²-bis­[dichloro­platinum(II)]

In the title compounds, [PtCl₂(C₃H₁₀N₂)], (I), [PdCl₂(C₃H₁₀N₂)], (II), and [Pt₂Cl₄(C₁₀H₂₆N₄)], (III), each metal atom lies in a distorted cis-square coordination geometry. Compounds (I) and (II) are isostructural, and each complex has a mirror plane through the metal atom and the middle C atom of the propane-1,3-diamine ligand. In (III), the binuclear complex [Pt₂Cl₄(spn)] has an inversion center at the middle of the 4,9-diaza­dodecane-1,12-diamine (spermine, spn) ligand. The six-membered chelate rings in (III) adopt a chair form, which is unsymmetrical and less flattened than those in (I) and (II). In all three crystal structures, there are inter­molecular N-H...Cl hydrogen bonds.

S1. Comment

cis-Diamminedichloroplatinum(II) (cisplatin) is known as an anticancer agent against a wide variety of human tumors, especially testicular and ovarian cancers (Siddik, 2003; Zhang & Lippard, 2003). However, its use is limited becuase of the toxic side effects and the development of resistance in tumor cells. Therefore, it is important to design new Pt^II compounds with improved pharmacological properties and a broader range of anticancer activity.

On the other hand, it is known that polyamines play an important role in the syntheses of nucleic acids and protein, in the structure of the cell membrane, and in the modulation of neurophysiological function in mammalian system (Morgan, 1999). Numerous derivatives and analogues of biogenic polyamines, spermidine [N-(3-aminopropyl)-4-aminobutylamine, spd] and spermine [N,N'-bis(3-aminopropyl)-1,4-butanediamine, spn], have been synthesized with the aim of generating a new type of anticancer drugs (Seiler, 2005). The Pt^II or Pd^II complexes of these ligands have been also synthesized, their anticancer properties tested (Teixeira et al., 2004; Marques et al., 2002; McGregor et al., 2002; Hegmans et al., 2001; Amo-Ochoa et al., 1996; Navarro-Ranninger et al., 1994, 1992) and their crystal structures analyzed (Codina et al., 1999). Among them, Pt^II complexes of spn have been investigated for their antiproliferative and cytotoxic effects, and have been demonstrated to display irreversible anticancer properties against Hera and HSC-3 cell lines, and growth inhibition properties against THP-1 and MOLT-3 cell lines (Teixeira et al., 2004).

The Pt^II or Pd^II complexes of propane-1,3-diamine (tn) have also been used as model anticancer agents to study the interaction with DNA (Akdi et al., 2005; Alvarez-Valdes et al., 2002; Marzilli et al., 1980). In the present study, we report the crystal structures of the title compounds, namely [PtCl₂(tn)], (I), [PdCl₂(tn)], (II), and [Pt₂Cl₄(spn)], (III).

Compounds (I) and (II) are isostructural (Fig. 1). In each complex, M^II [Pt^II or Pd^II] and atom C2 of the tn ligand lie on a mirror plane. The metal atom is coordinated by two N atoms from the tn ligand and two Cl atoms, which form a slightly distorted cis-square coordination geometry. The M^II atom and the four coordinated atoms are coplanar [the r.m.s. deviation of the fitted atoms is 0.016 Å for (I) and 0.022 Å for (II)]. The metal atom and the tn ligand form a six-membered chelate ring, which adopts a chair form.

The M^II—Cl and M^II—N bond lengths in (I) and (II) (Tables 1 and 3) are comparable to those in [PtCl₂(en)] and [PdCl₂(en)] (en is 1,2-ethylenediamine; Iball et al., 1975) and cis-[PtCl₂(NH₃)₂] (Milburn & Truter, 1966) [M^II—Cl = 2.288 (8)–2.333 (9) Å and M^II—N = 1.95 (3)–2.08 (3) Å], although the five-membered chelate rings of the en ligands have smaller N—M^II—N bond angles [73 (2)–87 (2)°] than in (I) and (II). The shortest intermolecular distances between the metal atoms are 3.646 (4) Å in (I) and 3.586 (3) Å in (II), which are considerably longer than those of the en complexes cited above [3.37–3.41 Å]; this difference may be due to the steric hindrance of the propane groups of the tn ligand.

In the crystal packing of (I) and (II), centrosymmetrically related complexes are aligned along the b axis (Fig. 2). The crystal structures are stabilized by N—H···Cl hydrogen bonds (Tables 2 and 4) between the amino groups of the tn ligand and the Cl atoms of the neighboring complexes along the b and c axes (Figs. 2 and 3), forming a lattice-like network.

In (III), the spn ligand coordinates to the two Pt^II atoms to form a binuclear complex (Fig. 4). Compound (III) is isostructural with the corresponding Pd^II complex, [Pd₂Cl₄(spn)] (Codina et al., 1999). A crystallographic inversion center is located at the middle of the butane chain of the spn ligand. The Pt^II atom is in a slightly distorted cis-square coordination geometry with two N and two Cl atoms. The Pt^II and four coordinated atoms are coplanar (the r.m.s. deviation of fitted atoms is 0.046 Å). The coordination bond lengths and bond angles (Table 5) are similar to those of (I). The Pt^II atom and the tn group of the spn ligand form a six-membered chelate ring, which adopts a chair form as in (I) and (II). However, the dihedral angles of the Pt1/N1/N2 and C1/C2/C3 planes with resepct to the N1/C1/N2/C3 plane are 46.4 (2) and 57.9 (4)°, respectively, indicating a less flattened conformation than those in (I) and (II). The corresponding dihedral angles are 24.3 (2) and 62.1 (5)° for (I), 22.2 (1) and 62.1 (3)° for (II), respectively. In addition, the torsion angles of the chelate rings (Table 5) show an unsymmetrical conformation around the Pt^II atom.

In the crystal packing of (III), there are intermolecular N—H···Cl hydrogen bonds (Table 6) between the primary amine groups of the spn ligand and the Cl atoms of neighboring complexes along the b axis, and between the secondary amine groups and the Cl atoms of neighboring complexes along the c axis, forming a three-dimensional network (Fig. 5).

S2. Experimental

For the preparation of (I), propane-1,3-diamine dihydrochloride (5 mg) was dissolved in 90% (v/v) dimethylformamide (DMF)/water and added to a K₂[PtCl₄] (14 mg) DMF solution. Colorless platelet crystals appeared after three months on evaporation of this mixture. For the prepartion of (II), propane-1,3-diamine dihydrochloride (5 mg) was dissolved in water, and then PdCl₂ (6 mg) in a 2 M NaCl aqueous solution and AgNO₃ (5.8 mg) dissolved in water were added. Brown needle-like crystals appeared from this mixture within one week. For the preparation of (III), spermine phosphate (5 mg) dissolved in a 50% (v/v) DMF/1 M NaCl aqueous solution was added to K₂[PtCl₄] (2.6 mg) dissolved in water. Colorless platelet crystals appeared after five months on evaporation of this mixture.

S3. Refinement

All H atoms were located in difference Fourier maps, and were then placed at idealized positions and treated as riding, with C—H distances of 0.97 Å, N—H distances for the primary amine groups of 0.90 Å and for the secondary amine groups of 0.91 Å, and U_iso(H) values of 1.2U_eq(carrier atom).

Computing details

For all compounds, data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005) and CRYSTALS (Watkin et al., 1996). Program(s) used to solve structure: SIR97 (Altomare et al., 1999) for (I), (II); SHELXS97 (Sheldrick, 1997) for (III). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure.

Figures

	Fig. 1. A view of the structure of (I) (left) and (II) (right), showing the atom-numbering schemes. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. A view of the crystal packing of (I), showing the centrosymmetric stacking along the b axis. Dashed lines show the N—H···Cl hydrogen bonds.
	Fig. 3. A view of the crystal packing of (II), showing the N—H···Cl hydrogen bonds along the b axis as dashed lines.
	Fig. 4. A view of the structure of (III), showing the atom-numbering scheme. Displacement ellipsoids are shown at the 50% probability level. [Symmetry code (i): −x, −y + 1, −z + 2.]
	Fig. 5. A view of the crystal packing of (III), showing the N—H···Cl hydrogen bonds as dashed lines.

(I) Dichloro(propane-1,3-diamine-κ²N,N')platinum(II)

Crystal data

[PtCl2(C3H10N2)]	F(000) = 616.00
Mr = 340.11	Dx = 2.861 Mg m^−3
Orthorhombic, Pbcm	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2c 2b	Cell parameters from 4958 reflections
a = 8.36 (1) Å	θ = 3.1–27.4°
b = 7.292 (8) Å	µ = 18.36 mm^−1
c = 12.950 (5) Å	T = 296 K
V = 789.5 (13) Å^3	Platelet, colorless
Z = 4	0.20 × 0.10 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	573 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.020
ω scans	θmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.152, Tmax = 0.401	k = −9→9
7821 measured reflections	l = −16→16
945 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.016	w = 1/[σ^2(Fo^2) + (0.020P)^2 + 0.2145P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.042	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.88 e Å^−3
945 reflections	Δρmin = −0.81 e Å^−3
41 parameters

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Pt1	0.00153 (3)	0.03892 (3)	0.2500	0.03543 (9)
Cl1	−0.18963 (14)	0.02167 (16)	0.11953 (8)	0.0531 (3)
N1	0.1680 (4)	0.0640 (5)	0.1357 (2)	0.0493 (9)
H1A	0.1313	0.0011	0.0808	0.059*
H1B	0.1705	0.1830	0.1173	0.059*
C1	0.3349 (5)	0.0061 (6)	0.1527 (3)	0.0538 (11)
H1C	0.3996	0.0445	0.0944	0.065*
H1D	0.3392	−0.1267	0.1565	0.065*
C2	0.4035 (8)	0.0855 (8)	0.2500	0.0480 (15)
H2A	0.3852	0.2169	0.2500	0.058*
H2B	0.5182	0.0657	0.2500	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.03252 (13)	0.04391 (14)	0.02984 (11)	0.00046 (11)	0.000	0.000
Cl1	0.0438 (6)	0.0752 (7)	0.0401 (5)	0.0076 (6)	−0.0049 (5)	−0.0033 (5)
N1	0.041 (2)	0.074 (2)	0.0328 (18)	−0.0058 (18)	0.0020 (15)	0.0004 (15)
C1	0.041 (3)	0.065 (2)	0.055 (2)	0.001 (2)	0.007 (2)	−0.009 (2)
C2	0.033 (4)	0.054 (3)	0.057 (3)	−0.001 (3)	0.000	0.000

Geometric parameters (Å, º)

Pt1—N1	2.040 (3)	C1—C2	1.501 (5)
Pt1—Cl1	2.3295 (17)	C1—H1C	0.9700
N1—C1	1.475 (6)	C1—H1D	0.9700
N1—H1A	0.9000	C2—H2A	0.9700
N1—H1B	0.9000	C2—H2B	0.9700
N1—Pt1—N1^i	93.0 (2)	N1—C1—C2	112.1 (4)
N1—Pt1—Cl1	86.98 (13)	N1—C1—H1C	109.2
N1^i—Pt1—Cl1	177.94 (10)	C2—C1—H1C	109.2
N1—Pt1—Cl1^i	177.94 (10)	N1—C1—H1D	109.2
N1^i—Pt1—Cl1^i	86.98 (13)	C2—C1—H1D	109.2
Cl1—Pt1—Cl1^i	92.99 (9)	H1C—C1—H1D	107.9
C1—N1—Pt1	120.8 (3)	C1—C2—C1^i	114.2 (5)
C1—N1—H1A	107.1	C1—C2—H2A	108.7
Pt1—N1—H1A	107.1	C1^i—C2—H2A	108.7
C1—N1—H1B	107.1	C1—C2—H2B	108.7
Pt1—N1—H1B	107.1	C1^i—C2—H2B	108.7
H1A—N1—H1B	106.8	H2A—C2—H2B	107.6
N1^i—Pt1—N1—C1	28.3 (4)	Pt1—N1—C1—C2	−50.5 (5)
Cl1—Pt1—N1—C1	−153.7 (3)	N1—C1—C2—C1^i	70.6 (6)

Symmetry code: (i) x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1^ii	0.90	2.65	3.369 (5)	138
N1—H1B···Cl1^iii	0.90	2.48	3.349 (6)	164

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

(II) dichloro(propane-1,3-diamine-κ²N,N')palladium(II)

Crystal data

[PdCl2(C3H10N2)]	F(000) = 488.00
Mr = 251.45	Dx = 2.158 Mg m^−3
Orthorhombic, Pbcm	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2c 2b	Cell parameters from 5562 reflections
a = 8.386 (7) Å	θ = 3.2–27.4°
b = 7.167 (5) Å	µ = 3.00 mm^−1
c = 12.88 (1) Å	T = 296 K
V = 774.1 (10) Å^3	Needle, brown
Z = 4	0.15 × 0.05 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	650 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.022
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.645, Tmax = 0.861	k = −9→8
7656 measured reflections	l = −16→16
923 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.017	w = 1/[σ^2(Fo^2) + (0.0243P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.043	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.26 e Å^−3
923 reflections	Δρmin = −0.60 e Å^−3
41 parameters

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Pd1	0.00708 (3)	0.04926 (3)	0.2500	0.02881 (9)
Cl1	−0.18302 (7)	0.03777 (8)	0.11832 (5)	0.04133 (15)
N1	0.1721 (2)	0.0737 (2)	0.13486 (15)	0.0408 (4)
H1A	0.1365	0.0060	0.0808	0.049*
H1B	0.1717	0.1938	0.1144	0.049*
C1	0.3417 (3)	0.0204 (3)	0.1518 (2)	0.0449 (6)
H1C	0.4049	0.0617	0.0931	0.054*
H1D	0.3497	−0.1145	0.1558	0.054*
C2	0.4087 (3)	0.1044 (5)	0.2500	0.0397 (7)
H2A	0.3869	0.2373	0.2500	0.048*
H2B	0.5235	0.0884	0.2500	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.02779 (13)	0.03443 (14)	0.02421 (13)	0.00006 (11)	0.000	0.000
Cl1	0.0348 (3)	0.0578 (3)	0.0314 (3)	0.0039 (3)	−0.0055 (2)	−0.0022 (2)
N1	0.0366 (10)	0.0547 (11)	0.0313 (11)	−0.0047 (9)	0.0041 (8)	−0.0030 (8)
C1	0.0341 (11)	0.0548 (13)	0.0458 (14)	0.0018 (11)	0.0075 (11)	−0.0061 (11)
C2	0.0250 (15)	0.0446 (17)	0.049 (2)	−0.0032 (14)	0.000	0.000

Geometric parameters (Å, º)

Pd1—N1	2.036 (2)	C1—C2	1.509 (3)
Pd1—Cl1	2.3296 (15)	C1—H1C	0.9700
N1—C1	1.489 (3)	C1—H1D	0.9700
N1—H1A	0.9000	C2—H2A	0.9700
N1—H1B	0.9000	C2—H2B	0.9700
N1—Pd1—N1^i	93.52 (13)	N1—C1—C2	112.1 (2)
N1—Pd1—Cl1	86.42 (9)	N1—C1—H1C	109.2
N1^i—Pd1—Cl1	177.09 (5)	C2—C1—H1C	109.2
N1—Pd1—Cl1^i	177.09 (5)	N1—C1—H1D	109.2
N1^i—Pd1—Cl1^i	86.42 (9)	C2—C1—H1D	109.2
Cl1—Pd1—Cl1^i	93.49 (8)	H1C—C1—H1D	107.9
C1—N1—Pd1	121.34 (16)	C1—C2—C1^i	113.9 (3)
C1—N1—H1A	107.0	C1—C2—H2A	108.8
Pd1—N1—H1A	107.0	C1^i—C2—H2A	108.8
C1—N1—H1B	107.0	C1—C2—H2B	108.8
Pd1—N1—H1B	107.0	C1^i—C2—H2B	108.8
H1A—N1—H1B	106.7	H2A—C2—H2B	107.7
N1^i—Pd1—N1—C1	26.0 (2)	Pd1—N1—C1—C2	−49.0 (2)
Cl1—Pd1—N1—C1	−156.92 (16)	N1—C1—C2—C1^i	70.6 (3)

Symmetry code: (i) x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1^ii	0.90	2.61	3.359 (3)	141
N1—H1B···Cl1^iii	0.90	2.47	3.334 (3)	162

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

(III) µ-4,9-diazadodecane-1,12-diamine-κ²N¹,N⁴;κ²N⁹,N¹²– bis[dichlorodiplatinum(II)]

Crystal data

[Pt2Cl4(C10H26N4)]	F(000) = 676.00
Mr = 734.31	Dx = 2.657 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 8101 reflections
a = 8.86 (1) Å	θ = 3.1–27.5°
b = 8.018 (6) Å	µ = 15.80 mm^−1
c = 12.93 (1) Å	T = 123 K
β = 92.09 (4)°	Platelet, colorless
V = 917.9 (14) Å^3	0.10 × 0.10 × 0.05 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer	1725 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.040
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.089, Tmax = 0.455	k = −10→10
9030 measured reflections	l = −16→15
2105 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.3492P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.076	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 2.61 e Å^−3
2105 reflections	Δρmin = −2.71 e Å^−3
92 parameters

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Pt1	0.19858 (2)	0.16739 (2)	0.825909 (16)	0.02137 (10)
Cl1	0.45049 (17)	0.16947 (15)	0.78547 (15)	0.0351 (4)
Cl2	0.24417 (15)	0.03880 (16)	0.98396 (11)	0.0291 (3)
N1	0.1493 (5)	0.2662 (6)	0.6856 (4)	0.0283 (10)
H1A	0.1190	0.3724	0.6939	0.034*
H1B	0.2339	0.2682	0.6492	0.034*
N2	−0.0242 (5)	0.1749 (5)	0.8627 (4)	0.0226 (10)
H2	−0.0321	0.1075	0.9188	0.027*
C1	0.0288 (8)	0.1737 (7)	0.6241 (5)	0.0353 (15)
H1C	0.0578	0.0576	0.6175	0.042*
H1D	0.0184	0.2211	0.5552	0.042*
C2	−0.1197 (7)	0.1848 (7)	0.6765 (5)	0.0331 (14)
H2A	−0.1440	0.3017	0.6857	0.040*
H2B	−0.1974	0.1372	0.6307	0.040*
C3	−0.1262 (6)	0.0997 (7)	0.7794 (5)	0.0287 (12)
H3A	−0.0992	−0.0166	0.7710	0.034*
H3B	−0.2294	0.1034	0.8020	0.034*
C4	−0.0748 (7)	0.3426 (6)	0.8963 (5)	0.0276 (13)
H4A	−0.1773	0.3347	0.9199	0.033*
H4B	−0.0755	0.4181	0.8377	0.033*
C5	0.0268 (6)	0.4140 (7)	0.9830 (5)	0.0317 (13)
H5A	0.1292	0.4226	0.9596	0.038*
H5B	0.0276	0.3388	1.0418	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.02145 (14)	0.01958 (15)	0.02336 (16)	0.00114 (6)	0.00473 (9)	−0.00127 (7)
Cl1	0.0241 (7)	0.0303 (8)	0.0515 (11)	−0.0006 (4)	0.0121 (7)	0.0017 (6)
Cl2	0.0305 (7)	0.0335 (7)	0.0232 (7)	0.0054 (5)	0.0003 (5)	−0.0003 (5)
N1	0.033 (3)	0.026 (2)	0.027 (3)	0.0010 (18)	0.014 (2)	0.006 (2)
N2	0.027 (3)	0.020 (2)	0.021 (3)	0.0009 (15)	0.005 (2)	0.0025 (17)
C1	0.045 (4)	0.036 (4)	0.024 (3)	0.001 (2)	−0.001 (3)	0.000 (2)
C2	0.033 (3)	0.033 (3)	0.032 (4)	0.001 (2)	−0.009 (3)	−0.003 (2)
C3	0.024 (3)	0.028 (3)	0.034 (3)	−0.005 (2)	0.001 (2)	−0.003 (3)
C4	0.027 (3)	0.024 (3)	0.032 (3)	0.0083 (18)	0.005 (2)	−0.003 (2)
C5	0.037 (3)	0.034 (3)	0.024 (3)	0.010 (2)	0.002 (2)	−0.005 (2)

Geometric parameters (Å, º)

Pt1—N1	2.013 (5)	C1—H1D	0.9700
Pt1—N2	2.047 (5)	C2—C3	1.499 (9)
Pt1—Cl1	2.310 (3)	C2—H2A	0.9700
Pt1—Cl2	2.312 (2)	C2—H2B	0.9700
N1—C1	1.503 (8)	C3—H3A	0.9700
N1—H1A	0.9000	C3—H3B	0.9700
N1—H1B	0.9000	C4—C5	1.524 (8)
N2—C4	1.488 (6)	C4—H4A	0.9700
N2—C3	1.506 (7)	C4—H4B	0.9700
N2—H2	0.9100	C5—C5^i	1.527 (11)
C1—C2	1.504 (10)	C5—H5A	0.9700
C1—H1C	0.9700	C5—H5B	0.9700
N1—Pt1—N2	91.0 (2)	C3—C2—C1	115.8 (5)
N1—Pt1—Cl1	88.44 (14)	C3—C2—H2A	108.3
N2—Pt1—Cl1	177.87 (11)	C1—C2—H2A	108.3
N1—Pt1—Cl2	176.04 (13)	C3—C2—H2B	108.3
N2—Pt1—Cl2	86.94 (15)	C1—C2—H2B	108.3
Cl1—Pt1—Cl2	93.69 (7)	H2A—C2—H2B	107.4
C1—N1—Pt1	114.2 (3)	C2—C3—N2	114.3 (4)
C1—N1—H1A	108.7	C2—C3—H3A	108.7
Pt1—N1—H1A	108.7	N2—C3—H3A	108.7
C1—N1—H1B	108.7	C2—C3—H3B	108.7
Pt1—N1—H1B	108.7	N2—C3—H3B	108.7
H1A—N1—H1B	107.6	H3A—C3—H3B	107.6
C4—N2—C3	113.1 (4)	N2—C4—C5	112.3 (5)
C4—N2—Pt1	113.4 (3)	N2—C4—H4A	109.1
C3—N2—Pt1	112.4 (4)	C5—C4—H4A	109.1
C4—N2—H2	105.7	N2—C4—H4B	109.1
C3—N2—H2	105.7	C5—C4—H4B	109.1
Pt1—N2—H2	105.7	H4A—C4—H4B	107.9
N1—C1—C2	110.4 (5)	C4—C5—C5^i	111.7 (6)
N1—C1—H1C	109.6	C4—C5—H5A	109.3
C2—C1—H1C	109.6	C5^i—C5—H5A	109.3
N1—C1—H1D	109.6	C4—C5—H5B	109.3
C2—C1—H1D	109.6	C5^i—C5—H5B	109.3
H1C—C1—H1D	108.1	H5A—C5—H5B	107.9
N2—Pt1—N1—C1	−53.6 (4)	N1—C1—C2—C3	−65.7 (6)
Cl1—Pt1—N1—C1	128.5 (4)	C1—C2—C3—N2	65.1 (7)
N1—Pt1—N2—C4	−80.2 (4)	C4—N2—C3—C2	69.7 (6)
Cl2—Pt1—N2—C4	103.3 (4)	Pt1—N2—C3—C2	−60.3 (5)
N1—Pt1—N2—C3	49.7 (3)	C3—N2—C4—C5	178.1 (5)
Cl2—Pt1—N2—C3	−126.9 (3)	Pt1—N2—C4—C5	−52.5 (6)
Pt1—N1—C1—C2	65.1 (5)	N2—C4—C5—C5^i	−179.9 (6)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1^ii	0.90	2.48	3.376 (5)	177
N1—H1B···Cl2^ii	0.90	2.78	3.261 (5)	115
N2—H2···Cl2^iii	0.91	2.58	3.309 (6)	138

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