Di­chlorido­[N-(N,N-di­methyl­carbamimido­yl)-N′,N′,4-tri­methyl­benzohydrazonamide]­platinum(II) nitro­methane hemisolvate

Bolotin, D.S.; Bokach, N.A.; Haukka, M.

doi:10.1107/S1600536814003894

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Pages m131-m132

doi:10.1107/S1600536814003894

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Dichlorido[N-(N,N-dimethylcarbamimidoyl)-N′,N′,4-trimethylbenzohydrazonamide]platinum(II) nitromethane hemisolvate

Dmitrii S. Bolotin,^a Nadezha A. Bokach ^a and Matti Haukka ^b ^*

^aDepartment of Chemistry, Saint Petersburg State University, Universitetsky Pr. 26, 198504 Stary Petergof, Russian Federation, and ^bDepartment of Chemistry, University of Jyväskylä, Finland, PO Box 35, FI-40014University of Jyväskylä, Finland
^*Correspondence e-mail: matti.o.haukka@jyu.fi

(Received 3 January 2014; accepted 19 February 2014; online 12 March 2014)

In the title compound, [PtCl₂(C₁₃H₂₁N₅)]·0.5CH₃NO₂, the Pt^II atom is coordinated in a slightly distorted square-planar geometry by two Cl atoms and two N atoms of the bidentate ligand. The (1,3,5-triazapentadiene)Pt^II metalla ring is slightly bent and does not conjugate with the aromatic ring. In the crystal, N—H⋯Cl hydrogen bonds link the complex molecules, forming chains along [001]. The nitromethane solvent molecule shows half-occupancy and is disordered over two sets of sites about an inversion centre.

CCDC reference: 987902

Related literature

For the luminescent properties of 1,3,5-triazapentadiene metal complexes, see: Gushchin et al. (2008 ); Kopylovich & Pombeiro (2011 ); Sarova et al. (2006 ) and for the catalytic activity of related complexes, see: Kopylovich & Pombeiro (2011). For the synthesis of [PtCl₂(C₁₃H₂₁N₅)] and similar compounds, see: Bolotin et al. (2013 ). For standard bond lengths, see: Allen et al. (1987 ); Orpen et al. (1989 ).

Experimental

Crystal data

[PtCl₂(C₁₃H₂₁N₅)]·0.5CH₃NO₂
M_r = 543.86
Monoclinic, C 2/c
a = 20.7561 (3) Å
b = 15.1847 (3) Å
c = 14.5191 (2) Å
β = 126.255 (1)°
V = 3690.1 (1) Å³
Z = 8
Mo Kα radiation
μ = 7.91 mm⁻¹
T = 100 K
0.44 × 0.29 × 0.20 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: numerical (SADABS; Sheldrick, 2008a ) T_min = 0.130, T_max = 0.297
38976 measured reflections
9015 independent reflections
8276 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.015
wR(F²) = 0.035
S = 1.06
9015 reflections
226 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −1.01 e Å⁻³

Table 1
Selected bond lengths (Å)

Pt1—N5	1.9809 (11)
Pt1—N1	2.0309 (11)
Pt1—Cl1	2.3223 (3)
Pt1—Cl2	2.3279 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯Cl1ⁱ	0.87	2.45	3.2154 (11)	147
N5—H5N⋯Cl1ⁱⁱ	0.84	2.67	3.4598 (12)	157
Symmetry codes: (i) -x, -y+1, -z+2; (ii) $[-x, y, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: CrystalMaker (CrystalMaker Software, 2011 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 987902

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814003894/zq2215sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814003894/zq2215Isup2.hkl

checkCIF report

Introduction top

The title complex (I) was obtained in the framework of our project devoted to the intramolecular rearrangement of carbamimidoylamidoxime and dialkylcyanamide ligands to furnish amidrazone complexes (Bolotin et al., 2013). The luminescent properties of 1,3,5-triazapentadiene metal complexes and the catalytic activity of some related complexes have been reported in the literature (Gushchin et al., 2008; Kopylovich et al., 2011; Sarova et al., 2006).

Experimental top

Synthesis and crystallization top

The platinum complex was synthesized by the described method (Bolotin et al., 2013). Crystals of I suitable for X-ray diffraction were obtained by a slow evaporation of a nitromethane solution of the complex at room temperature in air.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The solvent of crystallization (MeNO₂) was disordered over two sites about an inversion centre with equal occupancies. The NH hydrogen atoms were located from the difference Fourier map but constrained to ride on their parent atom, with U_iso = 1.5 U_eq(parent atom). Other hydrogen atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.95-0.98 Å, and U_iso = 1.2-1.5 U_eq(parent atom). The highest peak is located 0.68 Å from atom Pt1 and the deepest hole is located 0.64 Å from atom Pt1.

Results and discussion top

Compound I crystallizes from MeNO₂ as hemisolvate [PtCl₂(C₁₃H₂₁N₅)].0.5MeNO₂. Nitromethane molecules incorporated in the crystals lattice are disordered over two sites with equal occupancies. The coordination polyhedron of platinum exhibits a typical square-planar geometry. All bond angles around the Pt^II center are close to 90°. The Pt–Cl distances (2.3223 (3) and 2.3279 (3) Å) are specific for the Pt^II–Cl bonds, the Pt–N_imine bond length of 1.9809 (11) Å is a characteristic value in (imine)Pt^II species, while the Pt–N_hydrazone bond length (2.0309 (11) Å) is characteristic for Pt^II–N^sp2 complexes (Orpen et al., 1989).

The C–N_imine and C–N_hydrazone bond lengths are typical C=N double bonds, equal to 1.2966 (16) Å and 1.3049 (16) Å, respectively, while the amide N–(C=N)_imine, N–(C=N)_hydrazone and the C–NMe₂ distances are close to normal single bond values [1.3826 (17), 1.3660 (17), and 1.3408 (17) Å, respectively] (Allen et al., 1987). The N–N distance of 1.4402 (16) Å is specific for a normal single N^sp2–N^sp3 bond (Allen et al., 1987).

In the molecular structure, the (1,3,5-triazapentadiene)Pt^II ring is slightly bent and does not conjugate with the aromatic ring. The dihedral angle between the mean plane of the aromatic ring C4/C10 and the atoms N1/C3/N3 is 73.76 (9)°. All bond angles in this metallacycle are close to 120°, except the (N=C)_imine–N–(C=N)_hydrazone angle, which is equal to 127.96 (11)° and the N–Pt–N angle, which is close to 90° [88.49 (5)°]. Weak intermolecular H-bondings between the amidoxime amide group and one of the chlorine atoms were observed in the crystal structure.

Related literature top

For the luminescent properties of 1,3,5-triazapentadiene metal complexes, see: Gushchin et al. (2008); Kopylovich & Pombeiro (2011); Sarova et al. (2006) and for the catalytic activity of related complexes, see: Kopylovich & Pombeiro (2011). For the synthesis of [PtCl₂(C₁₃H₂₁N₅)] and similar compounds, see: Bolotin et al. (2013). For standard bondlengths, see: Allen et al. (1987); Orpen et al. (1989).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: CrystalMaker (CrystalMaker Software, 2011); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008b).

Figures top

Fig. 1. View of the title complex. Thermal ellipsoids are drawn at the 50% probability level. Pt atoms are pale blue, chlorine, carbon, and nitrogen atoms are green, grey, and blue, respectively. The disordered nitromethane of crystallization has been omitted for clarity.

Dichlorido[N-(N,N-dimethylcarbamimidoyl)-N',N',4-trimethylbenzohydrazonamide]platinum(II) nitromethane hemisolvate top

Crystal data top

[PtCl₂(C₁₃H₂₁N₅)]·0.5CH₃NO₂	F(000) = 2096
M_r = 543.86	D_x = 1.958 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9933 reflections
a = 20.7561 (3) Å	θ = 3.2–36.4°
b = 15.1847 (3) Å	µ = 7.91 mm⁻¹
c = 14.5191 (2) Å	T = 100 K
β = 126.255 (1)°	Block, yellow
V = 3690.1 (1) Å³	0.44 × 0.29 × 0.20 mm
Z = 8

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	9015 independent reflections
Radiation source: fine-focus sealed tube	8276 reflections with I > 2σ(I)
Curved graphite crystal monochromator	R_int = 0.017
Detector resolution: 16 pixels mm^-1	θ_max = 36.5°, θ_min = 2.0°
ϕ scans and ω scans with κ offset	h = −34→33
Absorption correction: numerical (SADABS; Sheldrick, 2008a)	k = −25→24
T_min = 0.130, T_max = 0.297	l = −20→24
38976 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)] = 0.015	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.035	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0133P)² + 5.9064P] where P = (F_o² + 2F_c²)/3
9015 reflections	(Δ/σ)_max = 0.002
226 parameters	Δρ_max = 0.78 e Å⁻³
2 restraints	Δρ_min = −1.01 e Å⁻³

Crystal data top

[PtCl₂(C₁₃H₂₁N₅)]·0.5CH₃NO₂	V = 3690.1 (1) Å³
M_r = 543.86	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.7561 (3) Å	µ = 7.91 mm⁻¹
b = 15.1847 (3) Å	T = 100 K
c = 14.5191 (2) Å	0.44 × 0.29 × 0.20 mm
β = 126.255 (1)°

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	9015 independent reflections
Absorption correction: numerical (SADABS; Sheldrick, 2008a)	8276 reflections with I > 2σ(I)
T_min = 0.130, T_max = 0.297	R_int = 0.017
38976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.015	2 restraints
wR(F²) = 0.035	H-atom parameters constrained
S = 1.06	Δρ_max = 0.78 e Å⁻³
9015 reflections	Δρ_min = −1.01 e Å⁻³
226 parameters

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. 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)
Pt1	0.086711 (3)	0.544103 (3)	0.926821 (4)	0.01177 (1)
Cl1	0.101415 (19)	0.39718 (2)	0.89820 (3)	0.01527 (5)
Cl2	0.22139 (2)	0.56194 (2)	1.00525 (4)	0.02319 (7)
N1	0.06341 (7)	0.66831 (7)	0.95151 (10)	0.01384 (18)
N2	0.10725 (7)	0.74645 (8)	0.96392 (11)	0.0178 (2)
N3	−0.05540 (7)	0.62871 (8)	0.92740 (10)	0.01448 (18)
H3N	−0.0805	0.6409	0.9571	0.022*
N4	−0.15323 (7)	0.52601 (8)	0.81191 (10)	0.01497 (19)
N5	−0.02759 (7)	0.51555 (8)	0.84918 (10)	0.01401 (18)
H5N	−0.0494	0.4762	0.7988	0.021*
C1	0.11579 (9)	0.75208 (11)	0.87141 (14)	0.0222 (3)
H1A	0.1448	0.7003	0.8734	0.033*
H1B	0.1455	0.8055	0.8806	0.033*
H1C	0.0628	0.7542	0.7980	0.033*
C2	0.18337 (9)	0.75253 (11)	1.07686 (14)	0.0223 (3)
H2A	0.1735	0.7596	1.1346	0.033*
H2B	0.2134	0.8034	1.0793	0.033*
H2C	0.2143	0.6987	1.0925	0.033*
C3	0.00349 (8)	0.68722 (8)	0.95483 (11)	0.01326 (19)
C4	−0.00996 (8)	0.77467 (9)	0.98743 (11)	0.0143 (2)
C5	0.03328 (10)	0.80236 (10)	1.10020 (13)	0.0214 (3)
H5A	0.0757	0.7671	1.1591	0.026*
C6	0.01455 (10)	0.88207 (11)	1.12719 (14)	0.0241 (3)
H6	0.0446	0.9005	1.2047	0.029*
C7	−0.04716 (9)	0.93496 (10)	1.04312 (14)	0.0204 (3)
C8	−0.06930 (11)	1.01952 (11)	1.07194 (18)	0.0287 (3)
H8A	−0.1182	1.0107	1.0665	0.043*
H8B	−0.0783	1.0656	1.0182	0.043*
H8C	−0.0258	1.0374	1.1499	0.043*
C9	−0.09025 (9)	0.90607 (10)	0.93054 (14)	0.0220 (3)
H9	−0.1323	0.9416	0.8715	0.026*
C10	−0.07310 (9)	0.82650 (10)	0.90270 (13)	0.0196 (2)
H10	−0.1045	0.8072	0.8255	0.023*
C11	−0.07838 (8)	0.55407 (8)	0.86030 (11)	0.01253 (19)
C12	−0.17809 (9)	0.43894 (9)	0.76070 (13)	0.0182 (2)
H12A	−0.2021	0.4431	0.6790	0.027*
H12B	−0.2174	0.4151	0.7709	0.027*
H12C	−0.1315	0.3999	0.7977	0.027*
C13	−0.21699 (8)	0.58213 (10)	0.79291 (13)	0.0197 (2)
H13A	−0.2321	0.5628	0.8421	0.030*
H13B	−0.2634	0.5781	0.7127	0.030*
H13C	−0.1984	0.6433	0.8111	0.030*
O1	0.23109 (19)	0.25839 (19)	0.8531 (2)	0.0342 (6)	0.50
N6	0.24020 (19)	0.2509 (2)	0.9450 (3)	0.0313 (6)	0.50
C14	0.1897 (11)	0.1872 (12)	0.958 (2)	0.0371 (7)	0.50
H14A	0.1352	0.1861	0.8870	0.056*	0.50
H14B	0.1883	0.2062	1.0211	0.056*	0.50
H14C	0.2129	0.1280	0.9737	0.056*	0.50
O2	0.1983 (8)	0.1969 (8)	0.9556 (13)	0.0371 (7)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.01165 (2)	0.01170 (2)	0.01451 (2)	0.00007 (1)	0.00913 (2)	−0.00061 (1)
Cl1	0.01681 (12)	0.01324 (12)	0.01993 (12)	0.00183 (10)	0.01316 (11)	0.00001 (10)
Cl2	0.01519 (13)	0.02011 (15)	0.03501 (18)	−0.00179 (11)	0.01526 (14)	−0.00348 (13)
N1	0.0138 (4)	0.0127 (4)	0.0187 (5)	−0.0007 (3)	0.0116 (4)	−0.0007 (4)
N2	0.0186 (5)	0.0140 (5)	0.0267 (6)	−0.0036 (4)	0.0167 (5)	−0.0011 (4)
N3	0.0164 (4)	0.0130 (4)	0.0197 (5)	−0.0019 (4)	0.0138 (4)	−0.0030 (4)
N4	0.0124 (4)	0.0142 (5)	0.0196 (5)	−0.0008 (3)	0.0102 (4)	−0.0019 (4)
N5	0.0132 (4)	0.0136 (5)	0.0165 (4)	−0.0017 (4)	0.0095 (4)	−0.0027 (4)
C1	0.0186 (6)	0.0260 (7)	0.0252 (6)	−0.0016 (5)	0.0146 (5)	0.0058 (5)
C2	0.0220 (6)	0.0211 (6)	0.0266 (7)	−0.0084 (5)	0.0159 (6)	−0.0085 (5)
C3	0.0149 (5)	0.0120 (5)	0.0158 (5)	−0.0003 (4)	0.0106 (4)	−0.0001 (4)
C4	0.0155 (5)	0.0120 (5)	0.0192 (5)	−0.0003 (4)	0.0124 (5)	−0.0009 (4)
C5	0.0278 (7)	0.0177 (6)	0.0187 (6)	0.0067 (5)	0.0137 (5)	0.0000 (5)
C6	0.0300 (7)	0.0202 (7)	0.0243 (6)	0.0044 (5)	0.0172 (6)	−0.0040 (5)
C7	0.0229 (6)	0.0132 (5)	0.0346 (7)	0.0003 (5)	0.0222 (6)	−0.0019 (5)
C8	0.0349 (8)	0.0158 (6)	0.0492 (10)	0.0023 (6)	0.0326 (8)	−0.0035 (6)
C9	0.0180 (6)	0.0179 (6)	0.0303 (7)	0.0045 (5)	0.0144 (6)	0.0018 (5)
C10	0.0165 (5)	0.0180 (6)	0.0226 (6)	0.0025 (5)	0.0107 (5)	−0.0013 (5)
C11	0.0133 (5)	0.0117 (5)	0.0146 (5)	0.0000 (4)	0.0094 (4)	0.0005 (4)
C12	0.0175 (5)	0.0166 (6)	0.0221 (6)	−0.0038 (4)	0.0126 (5)	−0.0042 (5)
C13	0.0138 (5)	0.0198 (6)	0.0246 (6)	0.0040 (4)	0.0107 (5)	0.0023 (5)
O1	0.0462 (16)	0.0301 (13)	0.0322 (13)	0.0129 (12)	0.0263 (13)	0.0062 (10)
N6	0.0300 (14)	0.0254 (14)	0.0396 (16)	0.0101 (11)	0.0211 (13)	0.0053 (12)
C14	0.032 (3)	0.028 (3)	0.0494 (12)	−0.0033 (15)	0.0232 (15)	0.0019 (18)
O2	0.032 (3)	0.028 (3)	0.0494 (12)	−0.0033 (15)	0.0232 (15)	0.0019 (18)

Geometric parameters (Å, º) top

Pt1—N5	1.9809 (11)	C4—C10	1.3941 (19)
Pt1—N1	2.0309 (11)	C5—C6	1.396 (2)
Pt1—Cl1	2.3223 (3)	C5—H5A	0.9500
Pt1—Cl2	2.3279 (3)	C6—C7	1.388 (2)
N1—C3	1.3049 (16)	C6—H6	0.9500
N1—N2	1.4402 (16)	C7—C9	1.391 (2)
N2—C1	1.4576 (19)	C7—C8	1.504 (2)
N2—C2	1.459 (2)	C8—H8A	0.9800
N3—C3	1.3660 (17)	C8—H8B	0.9800
N3—C11	1.3826 (17)	C8—H8C	0.9800
N3—H3N	0.8702	C9—C10	1.386 (2)
N4—C11	1.3408 (17)	C9—H9	0.9500
N4—C12	1.4537 (18)	C10—H10	0.9500
N4—C13	1.4567 (18)	C12—H12A	0.9800
N5—C11	1.2966 (16)	C12—H12B	0.9800
N5—H5N	0.8399	C12—H12C	0.9800
C1—H1A	0.9800	C13—H13A	0.9800
C1—H1B	0.9800	C13—H13B	0.9800
C1—H1C	0.9800	C13—H13C	0.9800
C2—H2A	0.9800	O1—N6	1.237 (3)
C2—H2B	0.9800	N6—C14	1.518 (8)
C2—H2C	0.9800	C14—H14A	0.9800
C3—C4	1.4904 (18)	C14—H14B	0.9800
C4—C5	1.3875 (19)	C14—H14C	0.9800

N5—Pt1—N1	88.49 (5)	C10—C4—C3	118.53 (12)
N5—Pt1—Cl1	85.86 (3)	C4—C5—C6	120.05 (14)
N1—Pt1—Cl1	173.69 (3)	C4—C5—H5A	120.0
N5—Pt1—Cl2	172.48 (3)	C6—C5—H5A	120.0
N1—Pt1—Cl2	98.51 (3)	C7—C6—C5	121.33 (14)
Cl1—Pt1—Cl2	87.274 (12)	C7—C6—H6	119.3
C3—N1—N2	111.07 (11)	C5—C6—H6	119.3
C3—N1—Pt1	122.86 (9)	C6—C7—C9	117.95 (13)
N2—N1—Pt1	126.04 (8)	C6—C7—C8	121.61 (15)
N1—N2—C1	110.19 (11)	C9—C7—C8	120.41 (15)
N1—N2—C2	112.14 (11)	C7—C8—H8A	109.5
C1—N2—C2	113.01 (11)	C7—C8—H8B	109.5
C3—N3—C11	127.96 (11)	H8A—C8—H8B	109.5
C3—N3—H3N	114.3	C7—C8—H8C	109.5
C11—N3—H3N	117.7	H8A—C8—H8C	109.5
C11—N4—C12	120.52 (11)	H8B—C8—H8C	109.5
C11—N4—C13	123.69 (12)	C10—C9—C7	121.34 (14)
C12—N4—C13	115.29 (11)	C10—C9—H9	119.3
C11—N5—Pt1	128.23 (9)	C7—C9—H9	119.3
C11—N5—H5N	111.7	C9—C10—C4	120.30 (14)
Pt1—N5—H5N	119.9	C9—C10—H10	119.9
N2—C1—H1A	109.5	C4—C10—H10	119.9
N2—C1—H1B	109.5	N5—C11—N4	124.54 (12)
H1A—C1—H1B	109.5	N5—C11—N3	119.36 (12)
N2—C1—H1C	109.5	N4—C11—N3	116.09 (11)
H1A—C1—H1C	109.5	N4—C12—H12A	109.5
H1B—C1—H1C	109.5	N4—C12—H12B	109.5
N2—C2—H2A	109.5	H12A—C12—H12B	109.5
N2—C2—H2B	109.5	N4—C12—H12C	109.5
H2A—C2—H2B	109.5	H12A—C12—H12C	109.5
N2—C2—H2C	109.5	H12B—C12—H12C	109.5
H2A—C2—H2C	109.5	N4—C13—H13A	109.5
H2B—C2—H2C	109.5	N4—C13—H13B	109.5
N1—C3—N3	123.64 (12)	H13A—C13—H13B	109.5
N1—C3—C4	124.71 (12)	N4—C13—H13C	109.5
N3—C3—C4	111.65 (11)	H13A—C13—H13C	109.5
C5—C4—C10	118.99 (13)	H13B—C13—H13C	109.5
C5—C4—C3	122.20 (12)	O1—N6—C14	121.0 (10)

N5—Pt1—N1—C3	24.61 (11)	N3—C3—C4—C10	−70.06 (15)
Cl2—Pt1—N1—C3	−158.15 (10)	C10—C4—C5—C6	−1.5 (2)
N5—Pt1—N1—N2	−153.35 (11)	C3—C4—C5—C6	−175.32 (14)
Cl2—Pt1—N1—N2	23.89 (11)	C4—C5—C6—C7	0.2 (3)
C3—N1—N2—C1	−127.66 (12)	C5—C6—C7—C9	0.2 (2)
Pt1—N1—N2—C1	50.50 (15)	C5—C6—C7—C8	178.10 (16)
C3—N1—N2—C2	105.52 (13)	C6—C7—C9—C10	0.8 (2)
Pt1—N1—N2—C2	−76.31 (14)	C8—C7—C9—C10	−177.14 (15)
N1—Pt1—N5—C11	−23.40 (12)	C7—C9—C10—C4	−2.2 (2)
Cl1—Pt1—N5—C11	153.79 (12)	C5—C4—C10—C9	2.5 (2)
N2—N1—C3—N3	169.27 (12)	C3—C4—C10—C9	176.52 (13)
Pt1—N1—C3—N3	−8.97 (18)	Pt1—N5—C11—N4	−173.99 (10)
N2—N1—C3—C4	−10.04 (18)	Pt1—N5—C11—N3	5.04 (18)
Pt1—N1—C3—C4	171.73 (9)	C12—N4—C11—N5	12.4 (2)
C11—N3—C3—N1	−22.1 (2)	C13—N4—C11—N5	−159.13 (13)
C11—N3—C3—C4	157.24 (12)	C12—N4—C11—N3	−166.66 (12)
N1—C3—C4—C5	−76.83 (18)	C13—N4—C11—N3	21.81 (19)
N3—C3—C4—C5	103.79 (15)	C3—N3—C11—N5	24.5 (2)
N1—C3—C4—C10	109.32 (16)	C3—N3—C11—N4	−156.34 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···Cl1ⁱ	0.87	2.45	3.2154 (11)	147
N5—H5N···Cl1ⁱⁱ	0.84	2.67	3.4598 (12)	157

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

Selected bond lengths (Å) top

Pt1—N5	1.9809 (11)	Pt1—Cl1	2.3223 (3)
Pt1—N1	2.0309 (11)	Pt1—Cl2	2.3279 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···Cl1ⁱ	0.87	2.45	3.2154 (11)	146.6
N5—H5N···Cl1ⁱⁱ	0.84	2.67	3.4598 (12)	157.0

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

Acknowledgements

This work was supported by a Saint Petersburg State University research grant (2013–2015, 12.38.781.2013) and the RFBR 14–03-00080. Financial support provided by the Academy of Finland (project No. 139571) is also gratefully acknowledged.

References

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Volume 70| Part 4| April 2014| Pages m131-m132

doi:10.1107/S1600536814003894

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­chlorido­[N-(N,N-di­methyl­carbamimido­yl)-N′,N′,4-tri­methyl­benzohydrazonamide]­platinum(II) nitro­methane hemisolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Dichlorido[N-(N,N-dimethylcarbamimidoyl)-N′,N′,4-trimethylbenzohydrazonamide]platinum(II) nitromethane hemisolvate