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

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.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.022
• wR factor = 0.054
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.4
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.4
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2     ...          ? Check
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........         H8
                    C8     H8
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........         H8
                    H8     O2
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........         H8
                    C8     H8     O2
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2
PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density       1.57 eA-3
PLAT976_ALERT_2_C Negative Residual Density at 1.09A from N2     .      -0.47 eA-3

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ? Do !
PLAT007_ALERT_5_G Note: Number of Unrefined Donor-H Atoms ........          1
PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ...................         33 %
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            N4  -PT1 -N4  -C3     15.00 24.00   2.665   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            N4  -PT1 -N4  -C5   -155.00 24.00   2.665   1.555   1.555   1.555
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         73
              C21  -C20  -CL21    1.555   1.555   1.555             11.60 Deg.
PLAT793_ALERT_4_G The Model has Chirality at N2      (Verify) ....          S
PLAT793_ALERT_4_G The Model has Chirality at C3      (Verify) ....          S
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......          ! Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

The carbon- and nitrogen-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with U_iso(H) set to 1.5U_eq(C) and C–H 0.96 Å for the methyl groups, 1.2U_eq(C) and C–H 0.98 Å for the tertiary CH groups, 1.2U_eq(C) and C–H 0.93 Å for the carbon atoms of the benzene rings and aldehyde group, and 1.2U_eq(N) and N–H 0.91 Å for the tertiary NH groups.

Computing details

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

	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)

Crystal data

[PtCl2(C11H15ClN3O)2]·C7H5ClO	Z = 1
Mr = 887.97	F(000) = 438
Triclinic, P1	Dx = 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) Å^3	0.17 × 0.11 × 0.09 mm

Data collection

Agilent Xcalibur Eos diffractometer	3892 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3888 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 16.2096 pixels mm^-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −10→10
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.933, Tmax = 1.000	l = −14→14
13908 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.054	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0326P)^2] where P = (Fo^2 + 2Fc^2)/3
3892 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 1.63 e Å^−3
0 restraints	Δρmin = −1.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Pt1—N4	2.018 (2)	C9—H9B	0.9600
Pt1—N4^i	2.018 (2)	C9—H9C	0.9600
Pt1—Cl17	2.3087 (7)	C10—C11	1.381 (4)
Pt1—Cl17^i	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—C18^ii	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—C19^ii	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—N4^i	180.0	N2—C9—H9A	109.5
N4^i—Pt1—Cl17	90.47 (7)	N2—C9—H9B	109.5
N4—Pt1—Cl17	89.53 (7)	N2—C9—H9C	109.5
N4^i—Pt1—Cl17^i	89.53 (7)	H9A—C9—H9B	109.5
N4—Pt1—Cl17^i	90.47 (7)	H9A—C9—H9C	109.5
Cl17—Pt1—Cl17^i	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)	C18^ii—C19—H19	120.4
C5—N6—C8	120.6 (3)	C18^ii—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	C19^ii—C18—C20	119.9 (4)
N6—C8—H8A	109.5	C19^ii—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)	Cl17^i—Pt1—N4—C3	−119.0 (2)
C3—N4—C5—N6	−171.3 (3)	Cl17^i—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—C19^ii	0.1 (8)
N4^i—Pt1—N4—C3	15 (24)	C19—C20—C21—O2	−178.3 (15)
N4^i—Pt1—N4—C5	−155 (24)	C18^ii—C19—C20—C18	−0.1 (7)
N4—C3—C10—C11	−141.0 (3)	C18^ii—C19—C20—Cl21	−176.3 (4)
N4—C3—C10—C16	41.9 (4)	C18^ii—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—C19^ii	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—C19^ii	−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)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2^iii	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.