trans-Bis{2-chloro-6-[(3-hydroxy­benzyl)amino]-9-isopropyl­purine-κN⁷}platinum(II) dimethyl­formamide disolvate

The title complex, trans-[Pt^IICl₂(C₁₅H₁₆ClN₅O)₂]·2C₃H₇NO, is centrosymmetric, with square-planar coordination of the Pt atom within a trans-Cl₂N₂ donor set. The complex is connected through O—H...O hydrogen bonds to two dimethyl­formamide solvent mol­ecules. The complex is the first structural example of a Pt^II complex involving two coordinated cyclin-dependent kinase inhibitors, viz. 2-chloro-6-[(3-hydroxy­benzyl)amino]-9-isopropyl­purine.

Key indicators

• Single-crystal X-ray study
• T = 105 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.034
• wR factor = 0.086
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.73 Ratio
PLAT420_ALERT_2_C D-H Without Acceptor       N6     -   H6A    ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18A   ..  CL1     ..       2.90 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C3 H7 N O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

trans-Bis{2-chloro-6-[(3-hydroxybenzyl)amino]-9-isopropylpurine- κN⁷}platinum(II) dimethylformamide disolvate

Crystal data

[PtCl2(C15H16ClN5O)2]·2C3H7NO	F(000) = 1048
Mr = 1047.74	Dx = 1.701 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9013 reflections
a = 9.4136 (4) Å	θ = 1.9–29.5°
b = 20.0628 (10) Å	µ = 3.75 mm^−1
c = 10.9064 (5) Å	T = 105 K
β = 96.723 (5)°	Prism, yellow
V = 2045.65 (16) Å^3	0.5 × 0.45 × 0.3 mm
Z = 2

Data collection

Oxford Xcalibur2 diffractometer	3588 independent reflections
Radiation source: fine-focus sealed tube	3395 reflections with I > 2σ(I)
Enhance (Oxford Diffraction) monochromator	Rint = 0.028
Detector resolution: 16.3 pixels mm^-1	θmax = 25.0°, θmin = 2.7°
Rotation method, ω scans	h = −11→9
Absorption correction: multi-scan (Blessing, 1995)	k = −23→23
Tmin = 0.151, Tmax = 0.321	l = −12→12
12305 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 1.28	w = 1/[σ^2(Fo^2) + (0.0275P)^2 + P] where P = (Fo^2 + 2Fc^2)/3
3588 reflections	(Δ/σ)max = 0.001
264 parameters	Δρmax = 1.00 e Å^−3
0 restraints	Δρmin = −0.74 e Å^−3

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.

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
Pt1	0.5000	0.5000	0.5000	0.01439 (10)
Cl1	0.40035 (14)	0.37573 (7)	1.12244 (11)	0.0241 (3)
N1	0.4840 (4)	0.3793 (2)	0.9051 (4)	0.0172 (9)
O1	1.0556 (5)	0.1860 (2)	0.9201 (4)	0.0353 (10)
H1	1.1449	0.1899	0.9342	0.042*
Cl2	0.71343 (13)	0.51968 (7)	0.62102 (11)	0.0232 (3)
C2	0.4042 (5)	0.4116 (2)	0.9770 (4)	0.0163 (10)
N3	0.3252 (4)	0.4656 (2)	0.9581 (4)	0.0156 (8)
C4	0.3376 (5)	0.4903 (2)	0.8446 (4)	0.0156 (10)
C5	0.4206 (5)	0.4642 (2)	0.7588 (4)	0.0139 (10)
N6	0.5682 (4)	0.3703 (2)	0.7147 (4)	0.0183 (9)
H6A	0.5775	0.3879	0.6421	0.022*
C6	0.4942 (5)	0.4046 (2)	0.7921 (4)	0.0141 (10)
N7	0.3994 (4)	0.50356 (19)	0.6533 (4)	0.0137 (8)
C8	0.3064 (5)	0.5499 (2)	0.6764 (4)	0.0161 (10)
H8A	0.2722	0.5836	0.6192	0.019*
N9	0.2655 (4)	0.54402 (19)	0.7904 (4)	0.0136 (8)
C9	0.6337 (5)	0.3060 (2)	0.7447 (5)	0.0194 (11)
H9A	0.6326	0.2799	0.6675	0.023*
H9B	0.5740	0.2818	0.7990	0.023*
C10	0.7860 (5)	0.3082 (3)	0.8077 (5)	0.0200 (11)
C11	0.8548 (6)	0.2481 (3)	0.8379 (5)	0.0228 (11)
H11A	0.8052	0.2073	0.8206	0.027*
C12	0.9959 (6)	0.2471 (3)	0.8932 (5)	0.0221 (11)
C13	1.0692 (6)	0.3060 (3)	0.9187 (5)	0.0269 (12)
H13A	1.1656	0.3053	0.9559	0.032*
C14	1.0012 (6)	0.3658 (3)	0.8898 (5)	0.0271 (12)
H14A	1.0511	0.4065	0.9076	0.033*
C15	0.8596 (6)	0.3671 (3)	0.8345 (5)	0.0231 (11)
H15A	0.8137	0.4086	0.8152	0.028*
C16	0.1623 (5)	0.5865 (2)	0.8475 (5)	0.0190 (11)
H16A	0.1669	0.5736	0.9365	0.023*
C17	0.0135 (6)	0.5731 (3)	0.7887 (6)	0.0375 (15)
H17A	−0.0083	0.5256	0.7962	0.056*
H17B	0.0055	0.5854	0.7012	0.056*
H17C	−0.0544	0.5995	0.8302	0.056*
C18	0.2049 (7)	0.6586 (3)	0.8426 (6)	0.0344 (14)
H18A	0.3036	0.6639	0.8812	0.052*
H18B	0.1409	0.6856	0.8871	0.052*
H18C	0.1979	0.6731	0.7564	0.052*
O2	1.3289 (5)	0.1716 (2)	1.0016 (4)	0.0373 (11)
N8	1.5606 (5)	0.1500 (2)	1.0687 (4)	0.0237 (10)
C19	1.4540 (7)	0.1898 (3)	1.0282 (5)	0.0295 (13)
H19A	1.4749	0.2357	1.0188	0.035*
C20	1.5391 (6)	0.0796 (3)	1.0895 (6)	0.0285 (13)
H20A	1.4363	0.0702	1.0833	0.043*
H20B	1.5843	0.0675	1.1719	0.043*
H20C	1.5820	0.0537	1.0272	0.043*
C21	1.7070 (6)	0.1730 (3)	1.0968 (7)	0.0379 (15)
H21A	1.7137	0.2195	1.0706	0.057*
H21B	1.7703	0.1453	1.0530	0.057*
H21C	1.7356	0.1697	1.1860	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.01460 (15)	0.01732 (15)	0.01152 (15)	0.00196 (10)	0.00262 (10)	0.00142 (10)
Cl1	0.0291 (7)	0.0298 (7)	0.0142 (6)	0.0015 (5)	0.0062 (5)	0.0069 (5)
N1	0.0127 (19)	0.026 (2)	0.013 (2)	−0.0003 (17)	0.0027 (16)	0.0033 (17)
O1	0.033 (2)	0.027 (2)	0.044 (3)	0.0138 (18)	−0.002 (2)	−0.0014 (19)
Cl2	0.0144 (6)	0.0416 (8)	0.0138 (6)	0.0020 (5)	0.0026 (4)	0.0030 (5)
C2	0.020 (2)	0.018 (2)	0.012 (2)	−0.006 (2)	0.0031 (19)	0.0030 (19)
N3	0.020 (2)	0.015 (2)	0.012 (2)	−0.0025 (16)	0.0025 (16)	0.0005 (16)
C4	0.013 (2)	0.019 (3)	0.014 (2)	−0.0019 (19)	−0.0015 (19)	−0.0012 (19)
C5	0.014 (2)	0.015 (2)	0.013 (2)	−0.0016 (18)	0.0023 (18)	−0.0018 (18)
N6	0.022 (2)	0.021 (2)	0.013 (2)	0.0065 (18)	0.0049 (17)	0.0027 (17)
C6	0.015 (2)	0.014 (2)	0.014 (2)	−0.0014 (18)	0.0017 (18)	−0.0007 (19)
N7	0.015 (2)	0.017 (2)	0.0095 (19)	0.0019 (16)	0.0043 (16)	0.0026 (15)
C8	0.017 (2)	0.016 (2)	0.016 (2)	0.003 (2)	0.0028 (19)	0.0002 (19)
N9	0.017 (2)	0.0109 (19)	0.014 (2)	0.0026 (16)	0.0043 (16)	−0.0006 (15)
C9	0.025 (3)	0.017 (3)	0.018 (3)	0.006 (2)	0.007 (2)	0.000 (2)
C10	0.024 (3)	0.024 (3)	0.013 (2)	0.009 (2)	0.007 (2)	0.003 (2)
C11	0.030 (3)	0.023 (3)	0.017 (3)	0.003 (2)	0.006 (2)	−0.001 (2)
C12	0.026 (3)	0.026 (3)	0.014 (3)	0.012 (2)	0.002 (2)	0.001 (2)
C13	0.021 (3)	0.040 (3)	0.020 (3)	0.002 (2)	0.002 (2)	0.002 (2)
C14	0.028 (3)	0.028 (3)	0.026 (3)	0.000 (2)	0.006 (2)	0.001 (2)
C15	0.026 (3)	0.023 (3)	0.020 (3)	0.005 (2)	0.003 (2)	0.003 (2)
C16	0.021 (3)	0.018 (3)	0.019 (3)	0.005 (2)	0.006 (2)	−0.003 (2)
C17	0.024 (3)	0.041 (4)	0.048 (4)	0.005 (3)	0.003 (3)	−0.017 (3)
C18	0.036 (3)	0.021 (3)	0.049 (4)	0.000 (2)	0.018 (3)	−0.009 (3)
O2	0.034 (2)	0.035 (2)	0.039 (3)	0.0134 (19)	−0.011 (2)	−0.0093 (19)
N8	0.027 (2)	0.018 (2)	0.026 (2)	−0.0001 (19)	0.0044 (19)	0.0016 (19)
C19	0.038 (3)	0.026 (3)	0.023 (3)	0.004 (3)	0.001 (2)	−0.001 (2)
C20	0.030 (3)	0.021 (3)	0.036 (3)	0.004 (2)	0.009 (3)	−0.001 (2)
C21	0.030 (3)	0.032 (3)	0.051 (4)	−0.007 (3)	0.002 (3)	0.004 (3)

Geometric parameters (Å, º)

Pt1—N7	2.017 (4)	C11—H11A	0.9500
Pt1—N7^i	2.017 (4)	C12—C13	1.379 (8)
Pt1—Cl2	2.3052 (12)	C13—C14	1.380 (8)
Pt1—Cl2^i	2.3052 (12)	C13—H13A	0.9500
Cl1—C2	1.746 (5)	C14—C15	1.397 (8)
N1—C2	1.319 (7)	C14—H14A	0.9500
N1—C6	1.347 (6)	C15—H15A	0.9500
O1—C12	1.366 (6)	C16—C17	1.495 (8)
O1—H1	0.8400	C16—C18	1.503 (8)
C2—N3	1.315 (6)	C16—H16A	1.0000
N3—C4	1.351 (6)	C17—H17A	0.9800
C4—N9	1.371 (6)	C17—H17B	0.9800
C4—C5	1.389 (7)	C17—H17C	0.9800
C5—N7	1.390 (6)	C18—H18A	0.9800
C5—C6	1.410 (7)	C18—H18B	0.9800
N6—C6	1.344 (6)	C18—H18C	0.9800
N6—C9	1.451 (6)	O2—C19	1.235 (7)
N6—H6A	0.8800	N8—C19	1.317 (7)
N7—C8	1.322 (6)	N8—C20	1.447 (7)
C8—N9	1.349 (6)	N8—C21	1.451 (7)
C8—H8A	0.9500	C19—H19A	0.9500
N9—C16	1.484 (6)	C20—H20A	0.9800
C9—C10	1.517 (7)	C20—H20B	0.9800
C9—H9A	0.9900	C20—H20C	0.9800
C9—H9B	0.9900	C21—H21A	0.9800
C10—C15	1.383 (8)	C21—H21B	0.9800
C10—C11	1.391 (7)	C21—H21C	0.9800
C11—C12	1.393 (8)
N7—Pt1—N7^i	180	C13—C12—C11	120.3 (5)
N7—Pt1—Cl2	88.94 (12)	C12—C13—C14	119.4 (5)
N7^i—Pt1—Cl2	91.06 (12)	C12—C13—H13A	120.3
N7—Pt1—Cl2^i	91.06 (12)	C14—C13—H13A	120.3
N7^i—Pt1—Cl2^i	88.94 (12)	C13—C14—C15	120.6 (5)
Cl2—Pt1—Cl2^i	180	C13—C14—H14A	119.7
C2—N1—C6	117.7 (4)	C15—C14—H14A	119.7
C12—O1—H1	109.5	C10—C15—C14	120.3 (5)
N3—C2—N1	131.5 (5)	C10—C15—H15A	119.9
N3—C2—Cl1	114.3 (4)	C14—C15—H15A	119.9
N1—C2—Cl1	114.2 (4)	N9—C16—C17	110.1 (4)
C2—N3—C4	109.8 (4)	N9—C16—C18	110.3 (4)
N3—C4—N9	126.3 (4)	C17—C16—C18	113.5 (5)
N3—C4—C5	126.5 (5)	N9—C16—H16A	107.6
N9—C4—C5	107.1 (4)	C17—C16—H16A	107.6
C4—C5—N7	107.9 (4)	C18—C16—H16A	107.6
C4—C5—C6	116.4 (4)	C16—C17—H17A	109.5
N7—C5—C6	135.5 (4)	C16—C17—H17B	109.5
C6—N6—C9	123.4 (4)	H17A—C17—H17B	109.5
C6—N6—H6A	118.3	C16—C17—H17C	109.5
C9—N6—H6A	118.3	H17A—C17—H17C	109.5
N6—C6—N1	118.7 (4)	H17B—C17—H17C	109.5
N6—C6—C5	123.2 (4)	C16—C18—H18A	109.5
N1—C6—C5	118.0 (4)	C16—C18—H18B	109.5
C8—N7—C5	106.0 (4)	H18A—C18—H18B	109.5
C8—N7—Pt1	124.6 (3)	C16—C18—H18C	109.5
C5—N7—Pt1	129.1 (3)	H18A—C18—H18C	109.5
N7—C8—N9	112.4 (4)	H18B—C18—H18C	109.5
N7—C8—H8A	123.8	C19—N8—C20	121.9 (5)
N9—C8—H8A	123.8	C19—N8—C21	123.0 (5)
C8—N9—C4	106.6 (4)	C20—N8—C21	115.1 (5)
C8—N9—C16	127.4 (4)	O2—C19—N8	124.6 (6)
C4—N9—C16	125.9 (4)	O2—C19—H19A	117.7
N6—C9—C10	115.4 (4)	N8—C19—H19A	117.7
N6—C9—H9A	108.4	N8—C20—H20A	109.5
C10—C9—H9A	108.4	N8—C20—H20B	109.5
N6—C9—H9B	108.4	H20A—C20—H20B	109.5
C10—C9—H9B	108.4	N8—C20—H20C	109.5
H9A—C9—H9B	107.5	H20A—C20—H20C	109.5
C15—C10—C11	118.9 (5)	H20B—C20—H20C	109.5
C15—C10—C9	123.0 (5)	N8—C21—H21A	109.5
C11—C10—C9	118.1 (5)	N8—C21—H21B	109.5
C10—C11—C12	120.6 (5)	H21A—C21—H21B	109.5
C10—C11—H11A	119.7	N8—C21—H21C	109.5
C12—C11—H11A	119.7	H21A—C21—H21C	109.5
O1—C12—C13	122.8 (5)	H21B—C21—H21C	109.5
O1—C12—C11	116.9 (5)
C6—N1—C2—N3	2.3 (8)	Pt1—N7—C8—N9	−174.2 (3)
C6—N1—C2—Cl1	−178.9 (3)	N7—C8—N9—C4	0.2 (6)
N1—C2—N3—C4	−2.5 (7)	N7—C8—N9—C16	−179.4 (4)
Cl1—C2—N3—C4	178.8 (3)	N3—C4—N9—C8	−178.1 (5)
C2—N3—C4—N9	176.5 (5)	C5—C4—N9—C8	−0.7 (5)
C2—N3—C4—C5	−0.4 (7)	N3—C4—N9—C16	1.5 (8)
N3—C4—C5—N7	178.3 (4)	C5—C4—N9—C16	178.9 (4)
N9—C4—C5—N7	0.9 (5)	C6—N6—C9—C10	−89.7 (6)
N3—C4—C5—C6	2.9 (7)	N6—C9—C10—C15	−0.5 (7)
N9—C4—C5—C6	−174.5 (4)	N6—C9—C10—C11	−179.5 (4)
C9—N6—C6—N1	2.4 (7)	C15—C10—C11—C12	−0.6 (8)
C9—N6—C6—C5	−174.4 (4)	C9—C10—C11—C12	178.5 (5)
C2—N1—C6—N6	−176.2 (4)	C10—C11—C12—O1	179.9 (5)
C2—N1—C6—C5	0.7 (7)	C10—C11—C12—C13	0.0 (8)
C4—C5—C6—N6	173.9 (4)	O1—C12—C13—C14	−179.4 (5)
N7—C5—C6—N6	0.1 (9)	C11—C12—C13—C14	0.4 (8)
C4—C5—C6—N1	−3.0 (6)	C12—C13—C14—C15	−0.3 (8)
N7—C5—C6—N1	−176.7 (5)	C11—C10—C15—C14	0.7 (8)
C4—C5—N7—C8	−0.8 (5)	C9—C10—C15—C14	−178.3 (5)
C6—C5—N7—C8	173.3 (5)	C13—C14—C15—C10	−0.2 (8)
C4—C5—N7—Pt1	173.4 (3)	C8—N9—C16—C17	71.7 (6)
C6—C5—N7—Pt1	−12.4 (8)	C4—N9—C16—C17	−107.9 (6)
Cl2—Pt1—N7—C8	113.9 (4)	C8—N9—C16—C18	−54.3 (7)
Cl2^i—Pt1—N7—C8	−66.1 (4)	C4—N9—C16—C18	126.2 (5)
Cl2—Pt1—N7—C5	−59.3 (4)	C20—N8—C19—O2	−1.8 (9)
Cl2^i—Pt1—N7—C5	120.7 (4)	C21—N8—C19—O2	178.8 (6)
C5—N7—C8—N9	0.4 (5)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	1.84	2.637 (6)	159
C20—H20C···Cl2^ii	0.98	2.74	3.660 (6)	156
C20—H20A···Cl2^iii	0.98	2.83	3.706 (6)	149
C18—H18A···Cl1^iv	0.98	2.90	3.755 (6)	146

Symmetry codes: (ii) −x+5/2, y−1/2, −z+3/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z+2.