Dichloridobis[3-(4-chloro­phen­yl)-2,N,N-trimethyl-2,3-di­hydro-1,2,4-oxa­diazole-5-amine-κN4]platinum(II)–4-chloro­benzaldehyde (1/1)

Kritchenkov, A.S.; Gurzhiy, V.V.; Bokach, N.A.; Kalibabchuk, V.A.

doi:10.1107/S1600536813017376

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages m446-m447

doi:10.1107/S1600536813017376

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Dichloridobis[3-(4-chlorophenyl)-2,N,N-trimethyl-2,3-dihydro-1,2,4-oxadiazole-5-amine-κN⁴]platinum(II)–4-chlorobenzaldehyde (1/1)

Andreii S. Kritchenkov,^a Vladislav V. Gurzhiy,^b Nadezhda A. Bokach ^a ^* and Valentina A. Kalibabchuk ^c

^aDepartment of Chemistry, Saint Petersburg State University, Universitetsky Pr. 26, 198504 Stary Petergof, Russian Federation, ^bDepartment of Geology, Saint Petersburg State University, Universitetskaya Avenue 7/9, 199034, Saint Petersburg, Russian Federation, and ^cO.O. Bohomolets National Medical University, Department of General Chemistry, Shevchenko blvd 13, 01004 Kiev, Ukraine
^*Correspondence e-mail: bokach@nb17701.spb.edu_kalibabchuk@ukr.net

(Received 2 June 2013; accepted 24 June 2013; online 10 July 2013)

In the title 1:1 co-crystal, [PtCl₂(C₁₁H₁₄ClN₃O)₂]·C₇H₅ClO, the coordination polyhedron of the Pt^II atom is slightly distorted square-planar with the chloride and 2,3-dihydro-1,2,4-oxadiazole ligands mutually trans, as the Pt atom lies on an inversion center. The 4-chlorobenzaldehyde molecules are statistically disordered about an inversion centre with equal occupancies for the two positions. The Pt^II complex forms a three-dimensional structure through C—H⋯Cl and weaker C—H⋯O interactions with the 4-chlorobenzaldehyde molecule.

Related literature

For the synthesis of platinum complexes with 2,3-dihydro-1,2,4-oxadiazole ligands, see: Bokach et al. (2011 ); Kritchenkov et al. (2011 ). For related structures, see: Bokach et al. (2003 , 2011); Kritchenkov et al. (2011); Bokach & Kukushkin (2006 ); Gushchin et al. (2008 ); Kuznetsov & Kukushkin (2006 ); Fritsky et al. (2006 ); Penkova et al. (2009 ). For standard bond lengths, see: see: Allen et al. (1987 ).

Experimental

Crystal data

[PtCl₂(C₁₁H₁₅ClN₃O)₂]·C₇H₅ClO
M_r = 887.97
Triclinic, $[P \overline 1]$
a = 8.46436 (18) Å
b = 9.38481 (19) Å
c = 11.4373 (3) Å
α = 101.0381 (18)°
β = 104.9553 (19)°
γ = 96.3847 (17)°
V = 849.07 (3) Å³
Z = 1
Mo Kα radiation
μ = 4.57 mm⁻¹
T = 100 K
0.17 × 0.11 × 0.09 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.933, T_max = 1.000
13908 measured reflections
3892 independent reflections
3888 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.054
S = 1.06
3892 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 1.63 e Å⁻³
Δρ_min = −1.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2ⁱ	0.96	2.58	3.378 (9)	141
C12—H12⋯Cl17ⁱⁱ	0.93	2.70	3.589 (4)	160
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2012 ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813017376/sj5329sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813017376/sj5329Isup2.hkl

checkCIF report

Comment top

In the past decade, a great attention has been paid to metal-mediated cycloaddition (CA) of various dipoles to nitriles. Indeed, the activation of nitrile substrates by a metal center often results in promotion of CAs, which are not feasible in the so-called pure organic chemistry. In addition, metal-mediated CA represents an efficient route to free and/or coordinated heterocycles that could be either difficult to obtain or even inaccessible via metal-free protocols (Bokach et al., 2011; Bokach & Kukushkin, 2006). Furthermore, an interest in platinum complexes with 2,3-dihydro-1,2,4-oxadiazole as a ligand is caused by their potential applications in medicine.

While 2,3-dihydro-1,2,4-oxadiazoles are known, examples of 5-dialkylamino-2,3-dihydro-1,2,4-oxadiazoles and, in particular, their metal complexes are still rare. Therefore, the synthesis of new complexes with 5-dialkylamino-2,3-dihydro-1,2,4-oxadiazole ligands and studies of their properties represent important tasks. As an amplification of our investigations of metal-mediated CA (Bokach et al., 2011; Kuznetsov & Kukushkin, 2006) and the reactivity of metal-bound dialkylcyanamides (Kritchenkov et al., 2011; Bokach et al., 2003; Gushchin et al., 2008), we have synthesized and characterized the title co-crystal and report its molecular and crystal structure here.

In 1, the complex molecule contains one crystallographically independent Pt atom that lies on an inversion center and is coordinated by two equivalent Cl^- anions and two N atoms (Fig. 1) of the heterocyclic ligands each of which are mutually trans. The Pt(1)–N(1) bond length is typical for (imine)Pt^II species (Allen et al., 1987). The N(4)–C(5) (1.301 (4) Å) distance is characteristic for the N=C double bond (Fritsky et al., 2006; Penkova et al., 2009), while the N(4)–C(3) and N(2)–C(3) (1.476 (4) and 1.474 (4), respectively) are specific for the N–C single bonds (Allen et al., 1987). Both asymmetric C(3) atoms in the heterocyclic ligands exhibit the same configuration (RR/SS). The p-chlorobenzaldehyde molecules are statistically disordered about an inversion centre with equal occupancies for the two half-occupied positions.

The platinum complexes are arranged in layers parallel to the (001) plane (Fig. 2). The p-chlorobenzaldehyde molecules occupy sites in between the layers of platinum(II) complexes.

Related literature top

For the synthesis of platinum complexes with 2,3-dihydro-1,2,4-oxadiazole ligands, see: Bokach et al. (2011); Kritchenkov et al. (2011). For related structures, see: Bokach et al. (2003, 2011); Kritchenkov et al. (2011); Bokach & Kukushkin (2006); Gushchin et al. (2008); Kuznetsov & Kukushkin (2006); Fritsky et al. (2006); Penkova et al. (2009). For standard bond lengths, see: see: Allen et al. (1987).

Experimental top

The platinum complex was synthesized by a cycloaddition reaction between the complex trans-[PtCl₂(NCNMe₂)₂] and the nitrone p-ClC6H4C(H)=N(O)Me as described previously (Kritchenkov et al., 2011). Crystals of 1 were obtained from the reaction mixture by slow evaporation of the solvent (dichloromethane) at room temperature; p-chlorobenzaldehyde was generated in the reaction mixture by hydration of the nitrone in the undried solvent.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the C₂₂H₃₀Cl₄N₆O₂Pt complex in the structure of 1. Thermal ellipsoids are drawn at the 50% probability level. Pt atoms are blue, chlorine, carbon, nitrogen, and oxygen atoms are green, grey, pale blue, and red, respectively. Primed atoms are related to unprimed atoms by the symmetry operation -x+1, -y+1 -z.
	Fig. 2. Crystal structure of the C₂₂H₃₀Cl₄N₆O₂Pt.C₇H₅OCl associate, projection to the (010). Pt atoms are blue, chlorine, carbon,nitrogen, and oxygen atoms are green, grey, pale blue, and red, respectively.

Dichloridobis[3-(4-chlorophenyl)-2,N,N-trimethyl-2,3-dihydro-1,2,4-oxadiazole-5-amine-κN⁴]platinum(II)–4-chlorobenzaldehyde (1/1) top

Crystal data top

[PtCl₂(C₁₁H₁₅ClN₃O)₂]·C₇H₅ClO	Z = 1
M_r = 887.97	F(000) = 438
Triclinic, P1	D_x = 1.737 Mg m⁻³
a = 8.46436 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.38481 (19) Å	Cell parameters from 9801 reflections
c = 11.4373 (3) Å	θ = 2.5–31.7°
α = 101.0381 (18)°	µ = 4.57 mm⁻¹
β = 104.9553 (19)°	T = 100 K
γ = 96.3847 (17)°	Prism, colourless
V = 849.07 (3) Å³	0.17 × 0.11 × 0.09 mm

Data collection top

Agilent Xcalibur Eos diffractometer	3892 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3888 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 16.2096 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −10→10
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
T_min = 0.933, T_max = 1.000	l = −14→14
13908 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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0326P)²] where P = (F_o² + 2F_c²)/3
3892 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 1.63 e Å⁻³
0 restraints	Δρ_min = −1.21 e Å⁻³

Crystal data top

[PtCl₂(C₁₁H₁₅ClN₃O)₂]·C₇H₅ClO	γ = 96.3847 (17)°
M_r = 887.97	V = 849.07 (3) Å³
Triclinic, P1	Z = 1
a = 8.46436 (18) Å	Mo Kα radiation
b = 9.38481 (19) Å	µ = 4.57 mm⁻¹
c = 11.4373 (3) Å	T = 100 K
α = 101.0381 (18)°	0.17 × 0.11 × 0.09 mm
β = 104.9553 (19)°

Data collection top

Agilent Xcalibur Eos diffractometer	3892 independent reflections
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	3888 reflections with I > 2σ(I)
T_min = 0.933, T_max = 1.000	R_int = 0.036
13908 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.054	H-atom parameters constrained
S = 1.06	Δρ_max = 1.63 e Å⁻³
3892 reflections	Δρ_min = −1.21 e Å⁻³
211 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	0.5000	0.5000	0.0000	0.01562 (5)
O1	0.8747 (3)	0.5755 (3)	0.34126 (19)	0.0321 (5)
N2	0.9212 (3)	0.4486 (3)	0.2650 (2)	0.0290 (6)
H2	0.9972	0.4786	0.2273	0.035*
C3	0.7596 (4)	0.3810 (3)	0.1742 (3)	0.0243 (6)
H3	0.6936	0.3203	0.2112	0.029*
N4	0.6856 (3)	0.5130 (3)	0.1552 (2)	0.0209 (5)
C5	0.7499 (4)	0.6134 (3)	0.2577 (3)	0.0240 (6)
N6	0.7135 (3)	0.7450 (3)	0.2956 (2)	0.0281 (6)
C7	0.5711 (4)	0.8001 (4)	0.2268 (3)	0.0334 (7)
H7A	0.6050	0.8552	0.1723	0.050*
H7B	0.5293	0.8627	0.2843	0.050*
H7C	0.4856	0.7186	0.1788	0.050*
C8	0.8131 (5)	0.8425 (4)	0.4142 (3)	0.0451 (10)
H8A	0.7642	0.8272	0.4788	0.068*
H8B	0.8163	0.9432	0.4077	0.068*
H8C	0.9239	0.8209	0.4338	0.068*
C9	0.9849 (5)	0.3574 (4)	0.3496 (3)	0.0452 (10)
H9A	1.0813	0.4129	0.4134	0.068*
H9B	1.0142	0.2721	0.3045	0.068*
H9C	0.9012	0.3272	0.3869	0.068*
C10	0.7869 (4)	0.2884 (3)	0.0606 (3)	0.0230 (6)
C11	0.7575 (5)	0.1367 (4)	0.0400 (3)	0.0342 (7)
H11	0.7156	0.0919	0.0941	0.041*
C12	0.7907 (5)	0.0506 (4)	−0.0617 (3)	0.0434 (9)
H12	0.7705	−0.0516	−0.0765	0.052*
C13	0.8532 (5)	0.1191 (4)	−0.1391 (3)	0.0365 (8)
Cl14	0.89823 (18)	0.01398 (12)	−0.26699 (9)	0.0619 (3)
C15	0.8828 (4)	0.2708 (4)	−0.1219 (3)	0.0306 (7)
H15	0.9243	0.3150	−0.1764	0.037*
C16	0.8483 (4)	0.3547 (3)	−0.0206 (3)	0.0257 (6)
H16	0.8667	0.4569	−0.0070	0.031*
Cl17	0.34015 (9)	0.32493 (9)	0.05713 (7)	0.03003 (16)
C19	0.5885 (5)	0.4816 (5)	0.6159 (4)	0.0510 (11)
H19	0.6474	0.4686	0.6927	0.061*
C20	0.5665 (6)	0.3740 (5)	0.5084 (4)	0.0493 (11)
C18	0.4783 (5)	0.3921 (5)	0.3929 (4)	0.0479 (10)
H18	0.4643	0.3190	0.3217	0.057*
Cl21	0.6390 (5)	0.2036 (3)	0.5142 (4)	0.0640 (9)	0.50
C21	0.659 (3)	0.2527 (18)	0.522 (2)	0.081 (2)	0.50
H21	0.7255	0.2501	0.6005	0.097*	0.50
O2	0.6509 (12)	0.1563 (8)	0.4337 (7)	0.081 (2)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.01892 (8)	0.01346 (8)	0.01130 (7)	0.00185 (5)	0.00020 (5)	0.00142 (5)
O1	0.0370 (12)	0.0334 (13)	0.0173 (10)	0.0180 (10)	−0.0050 (9)	−0.0037 (9)
N2	0.0311 (13)	0.0305 (15)	0.0193 (12)	0.0135 (11)	−0.0004 (10)	−0.0033 (10)
C3	0.0280 (14)	0.0236 (15)	0.0188 (13)	0.0079 (12)	0.0013 (11)	0.0045 (11)
N4	0.0246 (12)	0.0176 (12)	0.0159 (11)	0.0040 (9)	−0.0003 (9)	0.0011 (9)
C5	0.0251 (14)	0.0276 (16)	0.0151 (13)	0.0071 (12)	0.0000 (11)	0.0017 (11)
N6	0.0340 (14)	0.0236 (13)	0.0170 (11)	0.0097 (11)	−0.0048 (10)	−0.0049 (10)
C7	0.0394 (18)	0.0260 (17)	0.0250 (15)	0.0147 (14)	−0.0038 (13)	−0.0047 (13)
C8	0.045 (2)	0.040 (2)	0.0297 (17)	0.0138 (16)	−0.0096 (15)	−0.0164 (15)
C9	0.053 (2)	0.048 (2)	0.0264 (17)	0.0291 (19)	−0.0062 (16)	0.0022 (16)
C10	0.0247 (14)	0.0207 (15)	0.0178 (13)	0.0064 (11)	−0.0022 (11)	0.0006 (11)
C11	0.051 (2)	0.0262 (17)	0.0257 (15)	0.0055 (15)	0.0084 (15)	0.0094 (13)
C12	0.074 (3)	0.0135 (16)	0.0358 (18)	0.0094 (16)	0.0061 (18)	0.0007 (14)
C13	0.054 (2)	0.0323 (19)	0.0212 (15)	0.0222 (16)	0.0059 (15)	−0.0002 (13)
Cl14	0.1140 (10)	0.0441 (6)	0.0333 (5)	0.0409 (6)	0.0248 (6)	0.0019 (4)
C15	0.0342 (16)	0.0305 (17)	0.0308 (16)	0.0112 (13)	0.0120 (14)	0.0087 (13)
C16	0.0235 (14)	0.0187 (15)	0.0309 (15)	0.0017 (11)	0.0043 (12)	0.0022 (12)
Cl17	0.0284 (4)	0.0283 (4)	0.0350 (4)	0.0005 (3)	0.0072 (3)	0.0162 (3)
C19	0.067 (3)	0.069 (3)	0.037 (2)	0.037 (2)	0.027 (2)	0.028 (2)
C20	0.071 (3)	0.058 (3)	0.044 (2)	0.042 (2)	0.037 (2)	0.028 (2)
C18	0.067 (3)	0.058 (3)	0.0366 (19)	0.031 (2)	0.0315 (19)	0.0178 (18)
Cl21	0.100 (2)	0.059 (2)	0.0583 (16)	0.0507 (19)	0.0399 (15)	0.0301 (19)
C21	0.145 (7)	0.062 (5)	0.059 (4)	0.064 (5)	0.043 (4)	0.023 (4)
O2	0.145 (7)	0.062 (5)	0.059 (4)	0.064 (5)	0.043 (4)	0.023 (4)

Geometric parameters (Å, º) top

Pt1—N4	2.018 (2)	C9—H9B	0.9600
Pt1—N4ⁱ	2.018 (2)	C9—H9C	0.9600
Pt1—Cl17	2.3087 (7)	C10—C11	1.381 (4)
Pt1—Cl17ⁱ	2.3087 (7)	C10—C16	1.385 (4)
O1—N2	1.490 (3)	C11—H11	0.9300
O1—C5	1.360 (3)	C11—C12	1.394 (5)
N2—H2	0.9100	C12—H12	0.9300
N2—C3	1.474 (4)	C12—C13	1.364 (5)
N2—C9	1.452 (4)	C13—Cl14	1.754 (3)
C3—H3	0.9800	C13—C15	1.385 (5)
C3—N4	1.476 (4)	C15—H15	0.9300
C3—C10	1.505 (4)	C15—C16	1.387 (4)
N4—C5	1.301 (4)	C16—H16	0.9300
C5—N6	1.325 (4)	C19—H19	0.9300
N6—C7	1.464 (4)	C19—C20	1.389 (6)
N6—C8	1.467 (4)	C19—C18ⁱⁱ	1.378 (6)
C7—H7A	0.9600	C20—C18	1.391 (5)
C7—H7B	0.9600	C20—Cl21	1.782 (5)
C7—H7C	0.9600	C20—C21	1.465 (18)
C8—H8A	0.9600	C18—C19ⁱⁱ	1.378 (6)
C8—H8B	0.9600	C18—H18	0.9300
C8—H8C	0.9600	C21—H21	0.9300
C9—H9A	0.9600	C21—O2	1.20 (2)

N4—Pt1—N4ⁱ	180.0	N2—C9—H9A	109.5
N4ⁱ—Pt1—Cl17	90.47 (7)	N2—C9—H9B	109.5
N4—Pt1—Cl17	89.53 (7)	N2—C9—H9C	109.5
N4ⁱ—Pt1—Cl17ⁱ	89.53 (7)	H9A—C9—H9B	109.5
N4—Pt1—Cl17ⁱ	90.47 (7)	H9A—C9—H9C	109.5
Cl17—Pt1—Cl17ⁱ	180.0	H9B—C9—H9C	109.5
C5—O1—N2	103.2 (2)	C11—C10—C3	119.9 (3)
O1—N2—H2	111.8	C11—C10—C16	119.8 (3)
C3—N2—O1	101.1 (2)	C16—C10—C3	120.2 (3)
C3—N2—H2	111.8	C10—C11—H11	119.9
C9—N2—O1	106.0 (2)	C10—C11—C12	120.1 (3)
C9—N2—H2	111.8	C12—C11—H11	119.9
C9—N2—C3	113.6 (3)	C11—C12—H12	120.6
N2—C3—H3	110.1	C13—C12—C11	118.8 (3)
N2—C3—N4	101.0 (2)	C13—C12—H12	120.6
N2—C3—C10	109.5 (2)	C12—C13—Cl14	119.9 (3)
N4—C3—H3	110.1	C12—C13—C15	122.6 (3)
N4—C3—C10	115.5 (2)	C15—C13—Cl14	117.5 (3)
C10—C3—H3	110.1	C13—C15—H15	121.1
C3—N4—Pt1	119.50 (17)	C13—C15—C16	117.8 (3)
C5—N4—Pt1	133.5 (2)	C16—C15—H15	121.1
C5—N4—C3	106.5 (2)	C10—C16—C15	120.9 (3)
N4—C5—O1	114.1 (3)	C10—C16—H16	119.6
N4—C5—N6	131.3 (3)	C15—C16—H16	119.6
N6—C5—O1	114.5 (2)	C20—C19—H19	120.4
C5—N6—C7	123.4 (2)	C18ⁱⁱ—C19—H19	120.4
C5—N6—C8	120.6 (3)	C18ⁱⁱ—C19—C20	119.1 (4)
C7—N6—C8	115.9 (3)	C19—C20—C18	121.0 (4)
N6—C7—H7A	109.5	C19—C20—Cl21	121.3 (3)
N6—C7—H7B	109.5	C19—C20—C21	116.0 (9)
N6—C7—H7C	109.5	C18—C20—Cl21	117.5 (4)
H7A—C7—H7B	109.5	C18—C20—C21	122.5 (9)
H7A—C7—H7C	109.5	C21—C20—Cl21	11.6 (10)
H7B—C7—H7C	109.5	C19ⁱⁱ—C18—C20	119.9 (4)
N6—C8—H8A	109.5	C19ⁱⁱ—C18—H18	120.1
N6—C8—H8B	109.5	C20—C18—H18	120.1
N6—C8—H8C	109.5	C20—C21—H21	119.7
H8A—C8—H8B	109.5	O2—C21—C20	120.5 (17)
H8A—C8—H8C	109.5	O2—C21—H21	119.7
H8B—C8—H8C	109.5

Pt1—N4—C5—O1	179.0 (2)	C9—N2—C3—C10	−88.6 (3)
Pt1—N4—C5—N6	0.1 (5)	C10—C3—N4—Pt1	41.0 (3)
O1—N2—C3—N4	36.0 (3)	C10—C3—N4—C5	−146.2 (3)
O1—N2—C3—C10	158.3 (2)	C10—C11—C12—C13	0.5 (5)
O1—C5—N6—C7	−172.6 (3)	C11—C10—C16—C15	−0.7 (4)
O1—C5—N6—C8	4.9 (5)	C11—C12—C13—Cl14	179.4 (3)
N2—O1—C5—N4	16.2 (3)	C11—C12—C13—C15	−1.1 (6)
N2—O1—C5—N6	−164.7 (3)	C12—C13—C15—C16	0.7 (5)
N2—C3—N4—Pt1	159.05 (18)	C13—C15—C16—C10	0.2 (5)
N2—C3—N4—C5	−28.1 (3)	Cl14—C13—C15—C16	−179.7 (2)
N2—C3—C10—C11	105.8 (3)	C16—C10—C11—C12	0.4 (5)
N2—C3—C10—C16	−71.3 (3)	Cl17—Pt1—N4—C3	61.0 (2)
C3—N4—C5—O1	7.6 (3)	Cl17ⁱ—Pt1—N4—C3	−119.0 (2)
C3—N4—C5—N6	−171.3 (3)	Cl17ⁱ—Pt1—N4—C5	70.5 (3)
C3—C10—C11—C12	−176.7 (3)	Cl17—Pt1—N4—C5	−109.5 (3)
C3—C10—C16—C15	176.4 (3)	C19—C20—C18—C19ⁱⁱ	0.1 (8)
N4ⁱ—Pt1—N4—C3	15 (24)	C19—C20—C21—O2	−178.3 (15)
N4ⁱ—Pt1—N4—C5	−155 (24)	C18ⁱⁱ—C19—C20—C18	−0.1 (7)
N4—C3—C10—C11	−141.0 (3)	C18ⁱⁱ—C19—C20—Cl21	−176.3 (4)
N4—C3—C10—C16	41.9 (4)	C18ⁱⁱ—C19—C20—C21	172.0 (11)
N4—C5—N6—C7	6.3 (6)	C18—C20—C21—O2	−6 (3)
N4—C5—N6—C8	−176.2 (4)	Cl21—C20—C18—C19ⁱⁱ	176.4 (4)
C5—O1—N2—C3	−32.6 (3)	Cl21—C20—C21—O2	61 (4)
C5—O1—N2—C9	−151.3 (3)	C21—C20—C18—C19ⁱⁱ	−171.4 (11)
C9—N2—C3—N4	149.1 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2ⁱⁱⁱ	0.96	2.58	3.378 (9)	141
C12—H12···Cl17^iv	0.93	2.70	3.589 (4)	160

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

Experimental details

Crystal data
Chemical formula	[PtCl₂(C₁₁H₁₅ClN₃O)₂]·C₇H₅ClO
M_r	887.97
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.46436 (18), 9.38481 (19), 11.4373 (3)
α, β, γ (°)	101.0381 (18), 104.9553 (19), 96.3847 (17)
V (Å³)	849.07 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	4.57
Crystal size (mm)	0.17 × 0.11 × 0.09

Data collection
Diffractometer	Agilent Xcalibur Eos diffractometer
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.933, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13908, 3892, 3888
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.054, 1.06
No. of reflections	3892
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.63, −1.21

Computer programs: CrysAlis PRO (Agilent, 2012), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2ⁱ	0.96	2.58	3.378 (9)	141
C12—H12···Cl17ⁱⁱ	0.93	2.70	3.589 (4)	160

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

Acknowledgements

This work was supported by Saint Petersburg State University research grant (2013–2015, 12.38.781.2013) and RFBR 12–03-33071. The XRD study was performed at the X-ray Diffraction Centre of Saint Petersburg State University.

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