cis-[(4R,5R)-4,5-Bis­(amino­methyl)-2,2-di­methyl-1,3-dioxolane-N,N'](malonato-O,O')­platinum(II), an anticancer agent

In the title compound, [Pt(C₃H₂O₄)(C₇H₁₆N₂O₂)], the Pt atom is coordinated to two O and two N atoms in a square-planar arrangement. The two independent mol­ecules, which have very similar structures, are approximately related by pseudo-twofold screw-axis symmetry. The six-membered chelate ring in the leaving ligand assumes a conformation intermediate between the half-chair and boat forms. The seven-membered ring in the carrier ligand assumes a twist-chair conformation and the oxolane ring assumes an envelope conformation. The crystal packing consists of extensive hydrogen-bonding networks which form two-dimensional molecular layers, and there are weak van der Waals interactions between these layers.

Computing details

Data collection: local program (Yoon et al., 1994); cell refinement: local program; data reduction: local program; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

cis-(Malonato)[(4R,5R)-4,5-bis(aminomethyl)-2,2-dimethyl- 1,3-dioxolane]platinum(II)

Crystal data

[Pt(C3H2O4)(C7H16N2O2)]	F(000) = 872
Mr = 457.35	Dx = 2.191 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.092 (8) Å	Cell parameters from 45 reflections
b = 30.78 (3) Å	θ = 7–20°
c = 7.126 (7) Å	µ = 10.15 mm^−1
β = 116.96 (12)°	T = 293 K
V = 1386 (2) Å^3	Prism, colourless
Z = 4	0.52 × 0.20 × 0.15 mm

Data collection

Rigaku AFC4 diffractometer	2954 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 27.5°, θmin = 1.3°
ω scans	h = −9→5
Absorption correction: empirical (using intensity measurements) ψ scan (North et al., 1968)	k = −39→39
Tmin = 0.054, Tmax = 0.218	l = −8→9
3891 measured reflections	3 standard reflections every 100 reflections
3465 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0511P)^2 + 10.883P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3465 reflections	Δρmax = 2.03 [0.82 Å from Pt] e Å^−3
343 parameters	Δρmin = −2.54 [0.81 Å from Pt] e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (3), 219 Friedel pairs

Special details

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.

Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 0.4263 (0.0433) x + 30.5742 (0.0659) y - 0.4267 (0.0489) z = 8.1040 (0.0431)

* -0.0639 (0.0152) O1 * 0.0650 (0.0155) O2 * 0.0624 (0.0149) N1 * -0.0635 (0.0151) N2 - 0.0244 (0.0153) Pt -0.6374 (0.0279) C1 - 1.3691 (0.0301) C2 - 0.5300 (0.0319) C3 - 0.5637 (0.0311) O3 - 0.4229 (0.0355) O4 1.3302 (0.0315) C4 1.3317 (0.0373) C7

Rms deviation of fitted atoms = 0.0637

- 0.6193 (0.0438) x + 30.5473 (0.0665) y - 0.2597 (0.0434) z = 2.9401 (0.0392)

Angle to previous plane (with approximate e.s.d.) = 1.72 (1/4)

* 0.0306 (0.0165) O1' * -0.0307 (0.0166) O2' * -0.0296 (0.0160) N1' * 0.0298 (0.0161) N2' 0.0401 (0.0161) Pt' 0.5653 (0.0310) C1' 1.4169 (0.0311) C2' 0.6416 (0.0346) C3' 0.4228 (0.0333) O3' 0.5368 (0.0383) O4' -1.2006 (0.0304) C4' -1.3081 (0.0350) C7'

Rms deviation of fitted atoms = 0.0302

1.4866 (0.0801) x + 23.3040 (0.2426) y - 4.6066 (0.0641) z = 7.1662 (0.0491)

Angle to previous plane (with approximate e.s.d.) = 38.19 (3/4)

* -0.0029 (0.0178) C3 * 0.0008 (0.0050) C2 * 0.0010 (0.0061) O2 * 0.0011 (0.0067) O4 0.2012 (0.0369) Pt 1.1676 (0.0325) C1

Rms deviation of fitted atoms = 0.0017

- 4.2269 (0.0677) x + 24.3521 (0.2244) y + 1.0575 (0.0821) z = 3.5744 (0.1023)

Angle to previous plane (with approximate e.s.d.) = 56.03 (0.91)

* -0.0050 (0.0168) C1 * 0.0017 (0.0057) O1 * 0.0015 (0.0050) C2 * 0.0018 (0.0062) O3 0.2007 (0.0337) Pt 1.1861 (0.0353) C3

Rms deviation of fitted atoms = 0.0029

- 4.6196 (0.0699) x + 23.0127 (0.2844) y + 1.2870 (0.0921) z = 0.6141 (0.1359)

Angle to previous plane (with approximate e.s.d.) = 4.06 (1.76)

* 0.0300 (0.0183) C3' * -0.0090 (0.0057) C2' * -0.0102 (0.0061) O2' * -0.0108 (0.0066) O4' -0.1185 (0.0462) Pt' -1.1757 (0.0334) C1'

Rms deviation of fitted atoms = 0.0173

1.3683 (0.0826) x + 24.0667 (0.2092) y - 4.3880 (0.0614) z = 1.1093 (0.0917)

Angle to previous plane (with approximate e.s.d.) = 57.64 (0.97)

* -0.0079 (0.0154) C1' * 0.0028 (0.0055) O1' * 0.0023 (0.0045) C2' * 0.0028 (0.0053) O3' -0.2900 (0.0326) Pt' -1.1984 (0.0359) C3'

Rms deviation of fitted atoms = 0.0046

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pt	0.68737 (10)	0.27397 (2)	0.00844 (10)	0.03917 (19)
O1	0.6202 (17)	0.2675 (7)	−0.2982 (18)	0.036 (3)
O2	0.378 (2)	0.2716 (8)	−0.0599 (19)	0.051 (3)
O3	0.405 (2)	0.2437 (6)	−0.613 (2)	0.056 (4)
O4	0.060 (2)	0.2481 (6)	−0.281 (3)	0.058 (4)
O5	1.223 (2)	0.3764 (6)	0.397 (2)	0.060 (4)
O6	0.947 (3)	0.3927 (5)	0.454 (3)	0.074 (5)
N1	0.994 (3)	0.2819 (5)	0.068 (3)	0.044 (5)
H1A	1.0725	0.2636	0.1727	0.052*
H1B	1.0048	0.2733	−0.0473	0.052*
N2	0.743 (3)	0.2777 (11)	0.310 (2)	0.058 (6)
H2A	0.6350	0.2647	0.3217	0.069*
H2B	0.8608	0.2624	0.3884	0.069*
C1	0.460 (3)	0.2447 (7)	−0.423 (3)	0.041 (4)
C2	0.341 (3)	0.2204 (7)	−0.331 (3)	0.046 (5)
H2C	0.4356	0.1993	−0.2314	0.055*
H2D	0.2276	0.2045	−0.4422	0.055*
C3	0.248 (3)	0.2481 (7)	−0.220 (3)	0.049 (5)
C4	1.090 (3)	0.3255 (8)	0.126 (3)	0.052 (5)
H4A	1.0075	0.3462	0.0170	0.062*
H4B	1.2322	0.3249	0.1403	0.062*
C5	1.095 (4)	0.3394 (7)	0.334 (4)	0.056 (5)
H5	1.1570	0.3163	0.4387	0.068*
C6	0.885 (4)	0.3547 (7)	0.324 (4)	0.055 (5)
H6	0.7886	0.3631	0.1790	0.066*
C7	0.771 (4)	0.3250 (7)	0.404 (4)	0.049 (5)
H7A	0.6322	0.3371	0.3688	0.058*
H7B	0.8485	0.3234	0.5563	0.058*
C8	1.174 (4)	0.4007 (9)	0.540 (4)	0.066 (7)
C9	1.208 (5)	0.4483 (9)	0.526 (4)	0.091 (11)
H9A	1.1730	0.4636	0.6241	0.136*	0.50
H9B	1.1184	0.4584	0.3860	0.136*	0.50
H9C	1.3529	0.4536	0.5603	0.136*	0.50
H9D	1.2566	0.4534	0.4228	0.136*	0.50
H9E	1.3111	0.4587	0.6609	0.136*	0.50
H9F	1.0766	0.4635	0.4866	0.136*	0.50
C10	1.299 (4)	0.3829 (9)	0.755 (4)	0.075 (8)
H10A	1.2671	0.3990	0.8524	0.113*	0.50
H10B	1.4469	0.3855	0.7936	0.113*	0.50
H10C	1.2634	0.3529	0.7569	0.113*	0.50
H10D	1.3845	0.3593	0.7495	0.113*	0.50
H10E	1.2048	0.3727	0.8083	0.113*	0.50
H10F	1.3882	0.4053	0.8450	0.113*	0.50
Pt'	0.65555 (11)	0.11643 (2)	0.65629 (10)	0.03921 (19)
O1'	0.9643 (18)	0.1229 (5)	0.7215 (18)	0.041 (4)
O2'	0.727 (2)	0.1182 (10)	0.9643 (19)	0.056 (4)
O3'	1.277 (2)	0.1439 (6)	0.934 (3)	0.050 (4)
O4'	0.943 (3)	0.1438 (7)	1.281 (3)	0.067 (5)
O5'	0.280 (3)	0.0159 (6)	0.109 (3)	0.067 (4)
O6'	0.209 (3)	−0.0024 (5)	0.377 (3)	0.068 (5)
N1'	0.594 (2)	0.1103 (9)	0.346 (2)	0.041 (4)
H1'A	0.4871	0.1285	0.2704	0.049*
H1'B	0.7085	0.1197	0.3357	0.049*
N2'	0.348 (2)	0.1094 (9)	0.597 (2)	0.050 (5)
H2'A	0.3328	0.1201	0.7066	0.060*
H2'B	0.2665	0.1253	0.4828	0.060*
C1'	1.085 (3)	0.1442 (7)	0.878 (3)	0.043 (5)
C2'	1.001 (3)	0.1714 (7)	0.999 (3)	0.042 (4)
H2'C	0.9077	0.1936	0.9070	0.050*
H2'D	1.1185	0.1860	1.1136	0.050*
C3'	0.883 (3)	0.1444 (8)	1.088 (3)	0.052 (5)
C4'	0.541 (3)	0.0701 (7)	0.252 (3)	0.046 (5)
H4'A	0.6518	0.0494	0.3326	0.055*
H4'B	0.5320	0.0718	0.1116	0.055*
C5'	0.335 (3)	0.0545 (7)	0.236 (3)	0.052 (5)
H5'	0.2245	0.0768	0.1761	0.063*
C6'	0.346 (4)	0.0347 (8)	0.447 (4)	0.059 (5)
H6'	0.4909	0.0254	0.5408	0.070*
C7'	0.270 (4)	0.0637 (8)	0.560 (4)	0.054 (5)
H7'A	0.3051	0.0507	0.6955	0.065*
H7'B	0.1168	0.0646	0.4822	0.065*
C8'	0.133 (4)	−0.0080 (10)	0.158 (4)	0.065 (7)
C9'	0.155 (4)	−0.0538 (11)	0.113 (4)	0.084 (8)
H9'A	0.0999	−0.0576	−0.0367	0.126*	0.50
H9'B	0.0772	−0.0718	0.1634	0.126*	0.50
H9'C	0.3015	−0.0618	0.1811	0.126*	0.50
H9'D	0.2192	−0.0699	0.2419	0.126*	0.50
H9'E	0.2418	−0.0557	0.0418	0.126*	0.50
H9'F	0.0176	−0.0657	0.0241	0.126*	0.50
C10'	−0.091 (5)	0.0092 (10)	0.039 (5)	0.090 (9)
H10G	−0.1395	0.0048	−0.1095	0.135*	0.50
H10H	−0.0926	0.0396	0.0665	0.135*	0.50
H10I	−0.1819	−0.0060	0.0831	0.135*	0.50
H10J	−0.1365	0.0208	0.1362	0.135*	0.50
H10K	−0.1834	−0.0141	−0.0397	0.135*	0.50
H10L	−0.0941	0.0316	−0.0564	0.135*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt	0.0358 (4)	0.0460 (4)	0.0366 (3)	−0.0024 (3)	0.0172 (3)	−0.0016 (3)
O1	0.032 (5)	0.042 (9)	0.042 (6)	−0.003 (6)	0.023 (5)	0.003 (7)
O2	0.051 (7)	0.063 (8)	0.044 (7)	−0.027 (9)	0.025 (6)	−0.008 (9)
O3	0.043 (8)	0.090 (13)	0.032 (7)	0.003 (9)	0.015 (6)	0.001 (8)
O4	0.027 (6)	0.092 (13)	0.058 (9)	−0.002 (8)	0.023 (6)	0.004 (9)
O5	0.051 (8)	0.075 (11)	0.059 (9)	−0.032 (8)	0.030 (7)	−0.020 (8)
O6	0.069 (10)	0.050 (9)	0.103 (14)	−0.003 (8)	0.040 (10)	−0.022 (9)
N1	0.052 (9)	0.032 (11)	0.047 (9)	−0.004 (7)	0.022 (7)	−0.009 (7)
N2	0.049 (9)	0.092 (17)	0.033 (7)	−0.031 (13)	0.020 (7)	−0.009 (11)
C1	0.036 (9)	0.047 (11)	0.046 (10)	0.000 (8)	0.024 (8)	0.001 (9)
C2	0.046 (11)	0.059 (13)	0.046 (11)	−0.007 (9)	0.032 (9)	0.005 (9)
C3	0.061 (12)	0.046 (11)	0.064 (13)	−0.017 (10)	0.049 (11)	−0.010 (10)
C4	0.044 (11)	0.066 (15)	0.060 (13)	0.002 (10)	0.036 (10)	0.003 (11)
C5	0.061 (13)	0.038 (10)	0.065 (13)	−0.020 (9)	0.023 (11)	−0.016 (9)
C6	0.060 (13)	0.049 (12)	0.059 (13)	−0.004 (10)	0.031 (11)	−0.011 (10)
C7	0.057 (12)	0.052 (12)	0.050 (11)	0.008 (10)	0.036 (10)	0.001 (9)
C8	0.051 (14)	0.057 (15)	0.075 (17)	−0.014 (11)	0.016 (12)	−0.018 (13)
C9	0.13 (3)	0.042 (14)	0.078 (18)	−0.024 (15)	0.024 (18)	0.011 (13)
C10	0.074 (17)	0.078 (18)	0.083 (18)	0.008 (14)	0.044 (15)	0.026 (14)
Pt'	0.0358 (4)	0.0469 (4)	0.0359 (3)	−0.0017 (3)	0.0170 (3)	−0.0020 (3)
O1'	0.033 (6)	0.056 (11)	0.032 (6)	0.004 (6)	0.014 (5)	−0.013 (6)
O2'	0.036 (6)	0.100 (13)	0.036 (6)	−0.018 (10)	0.019 (5)	−0.006 (10)
O3'	0.040 (8)	0.067 (11)	0.049 (8)	−0.007 (7)	0.024 (7)	−0.012 (8)
O4'	0.050 (9)	0.113 (15)	0.043 (9)	−0.022 (10)	0.026 (8)	−0.018 (9)
O5'	0.056 (9)	0.078 (11)	0.061 (9)	−0.005 (9)	0.021 (8)	−0.024 (9)
O6'	0.069 (10)	0.061 (10)	0.066 (10)	−0.038 (8)	0.022 (8)	−0.009 (8)
N1'	0.035 (7)	0.050 (12)	0.041 (7)	0.002 (8)	0.021 (6)	0.008 (9)
N2'	0.028 (7)	0.086 (16)	0.043 (8)	−0.018 (10)	0.022 (6)	−0.009 (11)
C1'	0.032 (9)	0.063 (13)	0.030 (8)	0.002 (8)	0.008 (7)	0.021 (9)
C2'	0.035 (9)	0.054 (12)	0.038 (9)	−0.003 (8)	0.018 (7)	−0.005 (8)
C3'	0.039 (10)	0.072 (15)	0.052 (12)	0.015 (10)	0.026 (9)	−0.003 (11)
C4'	0.048 (11)	0.049 (12)	0.047 (10)	−0.010 (9)	0.027 (9)	−0.017 (9)
C5'	0.060 (12)	0.041 (10)	0.056 (12)	−0.007 (9)	0.026 (10)	−0.015 (9)
C6'	0.063 (13)	0.063 (14)	0.064 (13)	0.003 (11)	0.041 (11)	0.012 (11)
C7'	0.049 (12)	0.059 (14)	0.056 (12)	−0.014 (11)	0.025 (10)	−0.012 (10)
C8'	0.064 (16)	0.062 (16)	0.063 (15)	−0.003 (12)	0.024 (13)	−0.018 (12)
C9'	0.073 (17)	0.08 (2)	0.087 (18)	−0.004 (15)	0.028 (14)	−0.028 (17)
C10'	0.11 (2)	0.070 (18)	0.08 (2)	−0.002 (17)	0.035 (18)	−0.006 (15)

Geometric parameters (Å, º)

Pt—N2	2.002 (15)	Pt'—O2'	2.018 (13)
Pt—O2	2.024 (13)	Pt'—O1'	2.032 (12)
Pt—O1	2.024 (12)	Pt'—N2'	2.035 (13)
Pt—N1	2.029 (17)	Pt'—N1'	2.056 (14)
O1—C1	1.29 (2)	O1'—C1'	1.24 (2)
O2—C3	1.31 (3)	O2'—C3'	1.33 (3)
O3—C1	1.23 (2)	O3'—C1'	1.24 (2)
O4—C3	1.20 (2)	O4'—C3'	1.24 (3)
O5—C5	1.40 (2)	O5'—C5'	1.43 (2)
O5—C8	1.43 (3)	O5'—C8'	1.44 (3)
O6—C6	1.43 (3)	O6'—C8'	1.41 (3)
O6—C8	1.45 (3)	O6'—C6'	1.43 (3)
N1—C4	1.48 (3)	N1'—C4'	1.38 (3)
N1—H1A	0.9000	N1'—H1'A	0.9000
N1—H1B	0.9000	N1'—H1'B	0.9000
N2—C7	1.58 (4)	N2'—C7'	1.49 (3)
N2—H2A	0.9000	N2'—H2'A	0.9000
N2—H2B	0.9000	N2'—H2'B	0.9000
C1—C2	1.48 (2)	C1'—C2'	1.50 (3)
C2—C3	1.50 (3)	C2'—C3'	1.51 (3)
C2—H2C	0.9700	C2'—H2'C	0.9700
C2—H2D	0.9700	C2'—H2'D	0.9700
C4—C5	1.52 (3)	C4'—C5'	1.50 (3)
C4—H4A	0.9700	C4'—H4'A	0.9700
C4—H4B	0.9700	C4'—H4'B	0.9700
C5—C6	1.54 (3)	C5'—C6'	1.59 (3)
C5—H5	0.9800	C5'—H5'	0.9800
C6—C7	1.49 (3)	C6'—C7'	1.45 (3)
C6—H6	0.9800	C6'—H6'	0.9800
C7—H7A	0.9700	C7'—H7'A	0.9700
C7—H7B	0.9700	C7'—H7'B	0.9700
C8—C10	1.48 (4)	C8'—C9'	1.47 (4)
C8—C9	1.50 (4)	C8'—C10'	1.51 (4)
C9—H9A	0.9600	C9'—H9'A	0.9600
C9—H9B	0.9600	C9'—H9'B	0.9600
C9—H9C	0.9600	C9'—H9'C	0.9600
C9—H9D	0.9600	C9'—H9'D	0.9600
C9—H9E	0.9600	C9'—H9'E	0.9600
C9—H9F	0.9600	C9'—H9'F	0.9600
C10—H10A	0.9600	C10'—H10G	0.9600
C10—H10B	0.9600	C10'—H10H	0.9600
C10—H10C	0.9600	C10'—H10I	0.9600
C10—H10D	0.9600	C10'—H10J	0.9600
C10—H10E	0.9600	C10'—H10K	0.9600
C10—H10F	0.9600	C10'—H10L	0.9600
N2—Pt—O2	85.7 (6)	O2'—Pt'—O1'	92.1 (5)
N2—Pt—O1	176.8 (11)	O2'—Pt'—N2'	86.9 (6)
O2—Pt—O1	92.2 (5)	O1'—Pt'—N2'	178.8 (8)
N2—Pt—N1	95.6 (7)	O2'—Pt'—N1'	175.8 (14)
O2—Pt—N1	174.9 (9)	O1'—Pt'—N1'	86.4 (6)
O1—Pt—N1	86.8 (6)	N2'—Pt'—N1'	94.6 (6)
C1—O1—Pt	120.0 (12)	C1'—O1'—Pt'	119.2 (12)
C3—O2—Pt	119.0 (14)	C3'—O2'—Pt'	117.2 (15)
C5—O5—C8	109.0 (17)	C5'—O5'—C8'	106.8 (17)
C6—O6—C8	111.7 (18)	C8'—O6'—C6'	110.3 (19)
C4—N1—Pt	118.8 (13)	C4'—N1'—Pt'	119.3 (16)
C4—N1—H1A	107.6	C4'—N1'—H1'A	107.5
Pt—N1—H1A	107.6	Pt'—N1'—H1'A	107.5
C4—N1—H1B	107.6	C4'—N1'—H1'B	107.5
Pt—N1—H1B	107.6	Pt'—N1'—H1'B	107.5
H1A—N1—H1B	107.1	H1'A—N1'—H1'B	107.0
C7—N2—Pt	115.8 (18)	C7'—N2'—Pt'	114.5 (16)
C7—N2—H2A	108.3	C7'—N2'—H2'A	108.6
Pt—N2—H2A	108.3	Pt'—N2'—H2'A	108.6
C7—N2—H2B	108.3	C7'—N2'—H2'B	108.6
Pt—N2—H2B	108.3	Pt'—N2'—H2'B	108.6
H2A—N2—H2B	107.4	H2'A—N2'—H2'B	107.6
O3—C1—O1	120.9 (18)	O3'—C1'—O1'	120 (2)
O3—C1—C2	121.0 (18)	O3'—C1'—C2'	118.8 (18)
O1—C1—C2	118.1 (17)	O1'—C1'—C2'	121.5 (16)
C1—C2—C3	114.8 (17)	C1'—C2'—C3'	111.8 (17)
C1—C2—H2C	108.6	C1'—C2'—H2'C	109.3
C3—C2—H2C	108.6	C3'—C2'—H2'C	109.3
C1—C2—H2D	108.6	C1'—C2'—H2'D	109.3
C3—C2—H2D	108.6	C3'—C2'—H2'D	109.3
H2C—C2—H2D	107.6	H2'C—C2'—H2'D	107.9
O4—C3—O2	122.8 (19)	O4'—C3'—O2'	119 (2)
O4—C3—C2	119.2 (19)	O4'—C3'—C2'	120 (2)
O2—C3—C2	118.0 (18)	O2'—C3'—C2'	120.9 (18)
N1—C4—C5	109.6 (17)	N1'—C4'—C5'	111.0 (16)
N1—C4—H4A	109.8	N1'—C4'—H4'A	109.4
C5—C4—H4A	109.8	C5'—C4'—H4'A	109.4
N1—C4—H4B	109.8	N1'—C4'—H4'B	109.4
C5—C4—H4B	109.8	C5'—C4'—H4'B	109.4
H4A—C4—H4B	108.2	H4'A—C4'—H4'B	108.0
O5—C5—C4	105.8 (18)	O5'—C5'—C4'	106.7 (17)
O5—C5—C6	103.9 (17)	O5'—C5'—C6'	99.3 (17)
C4—C5—C6	116.4 (19)	C4'—C5'—C6'	115.1 (18)
O5—C5—H5	110.1	O5'—C5'—H5'	111.6
C4—C5—H5	110.1	C4'—C5'—H5'	111.6
C6—C5—H5	110.1	C6'—C5'—H5'	111.6
O6—C6—C7	108.4 (18)	O6'—C6'—C7'	108.7 (18)
O6—C6—C5	102.1 (17)	O6'—C6'—C5'	103.7 (18)
C7—C6—C5	118.7 (19)	C7'—C6'—C5'	114.4 (19)
O6—C6—H6	109.1	O6'—C6'—H6'	109.9
C7—C6—H6	109.1	C7'—C6'—H6'	109.9
C5—C6—H6	109.1	C5'—C6'—H6'	109.9
C6—C7—N2	112.6 (16)	C6'—C7'—N2'	118.4 (18)
C6—C7—H7A	109.1	C6'—C7'—H7'A	107.7
N2—C7—H7A	109.1	N2'—C7'—H7'A	107.7
C6—C7—H7B	109.1	C6'—C7'—H7'B	107.7
N2—C7—H7B	109.1	N2'—C7'—H7'B	107.7
H7A—C7—H7B	107.8	H7'A—C7'—H7'B	107.1
O5—C8—O6	101.1 (17)	O6'—C8'—O5'	104.3 (18)
O5—C8—C10	108 (2)	O6'—C8'—C9'	110 (2)
O6—C8—C10	114 (2)	O5'—C8'—C9'	106 (2)
O5—C8—C9	112 (3)	O6'—C8'—C10'	111 (2)
O6—C8—C9	108 (2)	O5'—C8'—C10'	112 (2)
C10—C8—C9	113 (2)	C9'—C8'—C10'	113 (2)
C8—C9—H9A	109.5	C8'—C9'—H9'A	109.5
C8—C9—H9B	109.5	C8'—C9'—H9'B	109.5
H9A—C9—H9B	109.5	H9'A—C9'—H9'B	109.5
C8—C9—H9C	109.5	C8'—C9'—H9'C	109.5
H9A—C9—H9C	109.5	H9'A—C9'—H9'C	109.5
H9B—C9—H9C	109.5	H9'B—C9'—H9'C	109.5
C8—C9—H9D	109.5	C8'—C9'—H9'D	109.5
H9A—C9—H9D	141.1	H9'A—C9'—H9'D	141.1
H9B—C9—H9D	56.3	H9'B—C9'—H9'D	56.3
H9C—C9—H9D	56.3	H9'C—C9'—H9'D	56.3
C8—C9—H9E	109.5	C8'—C9'—H9'E	109.5
H9A—C9—H9E	56.3	H9'A—C9'—H9'E	56.3
H9B—C9—H9E	141.1	H9'B—C9'—H9'E	141.1
H9C—C9—H9E	56.3	H9'C—C9'—H9'E	56.3
H9D—C9—H9E	109.5	H9'D—C9'—H9'E	109.5
C8—C9—H9F	109.5	C8'—C9'—H9'F	109.5
H9A—C9—H9F	56.3	H9'A—C9'—H9'F	56.3
H9B—C9—H9F	56.3	H9'B—C9'—H9'F	56.3
H9C—C9—H9F	141.1	H9'C—C9'—H9'F	141.1
H9D—C9—H9F	109.5	H9'D—C9'—H9'F	109.5
H9E—C9—H9F	109.5	H9'E—C9'—H9'F	109.5
C8—C10—H10A	109.5	C8'—C10'—H10G	109.5
C8—C10—H10B	109.5	C8'—C10'—H10H	109.5
H10A—C10—H10B	109.5	H10G—C10'—H10H	109.5
C8—C10—H10C	109.5	C8'—C10'—H10I	109.5
H10A—C10—H10C	109.5	H10G—C10'—H10I	109.5
H10B—C10—H10C	109.5	H10H—C10'—H10I	109.5
C8—C10—H10D	109.5	C8'—C10'—H10J	109.5
H10A—C10—H10D	141.1	H10G—C10'—H10J	141.1
H10B—C10—H10D	56.3	H10H—C10'—H10J	56.3
H10C—C10—H10D	56.3	H10I—C10'—H10J	56.3
C8—C10—H10E	109.5	C8'—C10'—H10K	109.5
H10A—C10—H10E	56.3	H10G—C10'—H10K	56.3
H10B—C10—H10E	141.1	H10H—C10'—H10K	141.1
H10C—C10—H10E	56.3	H10I—C10'—H10K	56.3
H10D—C10—H10E	109.5	H10J—C10'—H10K	109.5
C8—C10—H10F	109.5	C8'—C10'—H10L	109.5
H10A—C10—H10F	56.3	H10G—C10'—H10L	56.3
H10B—C10—H10F	56.3	H10H—C10'—H10L	56.3
H10C—C10—H10F	141.1	H10I—C10'—H10L	141.1
H10D—C10—H10F	109.5	H10J—C10'—H10L	109.5
H10E—C10—H10F	109.5	H10K—C10'—H10L	109.5
N2—Pt—O1—C1	15 (22)	O2'—Pt'—O1'—C1'	−31.8 (17)
O2—Pt—O1—C1	−32.7 (17)	N2'—Pt'—O1'—C1'	−59 (53)
N1—Pt—O1—C1	152.3 (17)	N1'—Pt'—O1'—C1'	152.2 (16)
N2—Pt—O2—C3	−146 (2)	O1'—Pt'—O2'—C3'	36 (2)
O1—Pt—O2—C3	32.0 (19)	N2'—Pt'—O2'—C3'	−144 (2)
N1—Pt—O2—C3	110 (8)	N1'—Pt'—O2'—C3'	106 (12)
N2—Pt—N1—C4	−73.9 (18)	O2'—Pt'—N1'—C4'	37 (11)
O2—Pt—N1—C4	30 (8)	O1'—Pt'—N1'—C4'	106.9 (15)
O1—Pt—N1—C4	108.2 (16)	N2'—Pt'—N1'—C4'	−72.5 (16)
O2—Pt—N2—C7	−95.1 (15)	O2'—Pt'—N2'—C7'	−98.3 (16)
O1—Pt—N2—C7	−143 (20)	O1'—Pt'—N2'—C7'	−71 (52)
N1—Pt—N2—C7	79.9 (15)	N1'—Pt'—N2'—C7'	77.8 (15)
Pt—O1—C1—O3	173.1 (16)	Pt'—O1'—C1'—O3'	171.1 (15)
Pt—O1—C1—C2	−6 (3)	Pt'—O1'—C1'—C2'	−11 (2)
O3—C1—C2—C3	−119 (2)	O3'—C1'—C2'—C3'	−121 (2)
O1—C1—C2—C3	60 (3)	O1'—C1'—C2'—C3'	60 (2)
Pt—O2—C3—O4	−173.3 (18)	Pt'—O2'—C3'—O4'	−174.3 (18)
Pt—O2—C3—C2	6 (3)	Pt'—O2'—C3'—C2'	0 (3)
C1—C2—C3—O4	120 (2)	C1'—C2'—C3'—O4'	121 (2)
C1—C2—C3—O2	−60 (3)	C1'—C2'—C3'—O2'	−53 (3)
Pt—N1—C4—C5	63 (2)	Pt'—N1'—C4'—C5'	65 (2)
C8—O5—C5—C4	157.9 (19)	C8'—O5'—C5'—C4'	158.3 (19)
C8—O5—C5—C6	35 (2)	C8'—O5'—C5'—C6'	38 (2)
N1—C4—C5—O5	168.8 (18)	N1'—C4'—C5'—O5'	171.8 (17)
N1—C4—C5—C6	−76 (2)	N1'—C4'—C5'—C6'	−79 (2)
C8—O6—C6—C7	125 (2)	C8'—O6'—C6'—C7'	126 (2)
C8—O6—C6—C5	−1 (3)	C8'—O6'—C6'—C5'	4 (2)
O5—C5—C6—O6	−20 (2)	O5'—C5'—C6'—O6'	−25 (2)
C4—C5—C6—O6	−135.8 (19)	C4'—C5'—C6'—O6'	−138.9 (18)
O5—C5—C6—C7	−139 (2)	O5'—C5'—C6'—C7'	−143.6 (19)
C4—C5—C6—C7	105 (2)	C4'—C5'—C6'—C7'	103 (2)
O6—C6—C7—N2	−166.1 (18)	O6'—C6'—C7'—N2'	−163.6 (18)
C5—C6—C7—N2	−50 (3)	C5'—C6'—C7'—N2'	−48 (3)
Pt—N2—C7—C6	−37 (2)	Pt'—N2'—C7'—C6'	−36 (3)
C5—O5—C8—O6	−34 (3)	C6'—O6'—C8'—O5'	20 (3)
C5—O5—C8—C10	85 (2)	C6'—O6'—C8'—C9'	133 (2)
C5—O5—C8—C9	−150 (2)	C6'—O6'—C8'—C10'	−101 (3)
C6—O6—C8—O5	20 (3)	C5'—O5'—C8'—O6'	−38 (3)
C6—O6—C8—C10	−96 (3)	C5'—O5'—C8'—C9'	−154.0 (19)
C6—O6—C8—C9	138 (2)	C5'—O5'—C8'—C10'	82 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3^i	0.90	2.23	3.01 (2)	144
N1—H1B···O4^ii	0.90	2.03	2.93 (2)	172
N2—H2A···O3^iii	0.90	2.00	2.89 (2)	170
N2—H2B···O4^i	0.90	2.17	2.91 (3)	138
N1′—H1′A···O3′^iv	0.90	2.22	2.96 (2)	139
N1′—H1′B···O4′^v	0.90	2.01	2.91 (2)	174
N2′—H2′A···O3′^vi	0.90	1.98	2.87 (2)	176
N2′—H2′B···O4′^iv	0.90	2.16	2.93 (3)	143

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