Literature DB >> 23794993

trans-Dichloridobis{2-chloro-6-[(3-fluoro-benz-yl)amino]-9-isopropyl-9H-purine-κN (7)}platinum(II).

Abstract

In the title compound, trans-[PtCl2(C15H15ClFN5)2], the Pt(II) atom, located on an inversion centre, is coordinated by the purine N atoms of the 2-chloro-6-[(3-fluoro-benz-yl)amino]-9-isopropyl-9H-purine ligands and two Cl atoms in a slightly distorted trans-square-planar coordination geometry [N-Pt-Cl angles = 89.91 (5) and 90.09 (5)°]. Weak intra-molecular N-H⋯Cl contacts occur. In the crystal, C-H⋯Cl and C-H⋯F contacts, as well as weak π-π stacking inter-actions [centroid-centroid distances = 3.5000 (11) and 3.6495 (12) Å] connect the mol-ecules into a three-dimensional architecture.

Entities: Chemical Disease Gene Species

Year: 2013 PMID： 23794993 PMCID： PMC3684891 DOI： 10.1107/S1600536813013202

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the structures of platinum(II) dichlorido complexes involving different 2-chloro-6-[(substituted-benzyl)amino]-9-isopropyl-9H-purine derivatives, see: Trávníček et al. (2006 ▶); Szüčová et al. (2008 ▶). For the synthesis of 2-chloro-6-[(substituted-benzyl)amino]-9-isopropyl-9H-purine derivatives, see: Štarha et al. (2009 ▶).

Experimental

Crystal data

[PtCl2(C15H15ClFN5)2] M = 905.53 Monoclinic, a = 9.37786 (13) Å b = 12.86530 (17) Å c = 14.2891 (2) Å β = 107.9165 (16)° V = 1640.36 (4) Å3 Z = 2 Mo Kα radiation μ = 4.65 mm−1 T = 105 K 0.35 × 0.35 × 0.35 mm

Data collection

Agilent Xcalibur Sapphire2 diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.293, T max = 0.293 13582 measured reflections 2881 independent reflections 2726 reflections with I > 2σ(I) R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.015 wR(F 2) = 0.037 S = 1.10 2881 reflections 216 parameters H-atom parameters constrained Δρmax = 0.52 e Å−3 Δρmin = −0.32 e Å−3 Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013202/jj2166sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013202/jj2166Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[PtCl₂(C₁₅H₁₅ClFN₅)₂]	F(000) = 888
M_r = 905.53	D_x = 1.833 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15658 reflections
a = 9.37786 (13) Å	θ = 3.0–31.7°
b = 12.86530 (17) Å	µ = 4.65 mm⁻¹
c = 14.2891 (2) Å	T = 105 K
β = 107.9165 (16)°	Prism, yellow-orange
V = 1640.36 (4) Å³	0.35 × 0.35 × 0.35 mm
Z = 2

Agilent Xcalibur Sapphire2 diffractometer	2881 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2726 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.010
Detector resolution: 8.3611 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −15→13
T_min = 0.293, T_max = 0.293	l = −16→16
13582 measured reflections

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) = 0.037	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0204P)² + 1.5464P] where P = (F_o² + 2F_c²)/3
2881 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
Pt1	0.0000	0.0000	0.0000	0.01222 (5)
Cl1	0.73503 (6)	0.18413 (6)	0.31702 (4)	0.03616 (16)
Cl2	−0.15533 (5)	0.11059 (4)	0.04896 (4)	0.02297 (12)
F1	0.32167 (15)	0.15374 (11)	−0.40416 (9)	0.0297 (3)
N1	0.52347 (19)	0.13487 (14)	0.15853 (12)	0.0174 (4)
N3	0.49172 (18)	0.08828 (14)	0.31434 (12)	0.0164 (4)
N6	0.34612 (19)	0.10095 (14)	0.00859 (12)	0.0176 (4)
H6A	0.2599	0.0723	−0.0239	0.021*
N7	0.1537 (2)	0.01264 (12)	0.13330 (14)	0.0145 (4)
N9	0.2482 (2)	0.01119 (12)	0.29616 (14)	0.0148 (4)
C2	0.5616 (2)	0.12816 (17)	0.25559 (15)	0.0189 (4)
C4	0.3566 (2)	0.05155 (15)	0.26050 (14)	0.0137 (4)
C5	0.2990 (2)	0.05145 (15)	0.15906 (14)	0.0137 (4)
C6	0.3894 (2)	0.09529 (15)	0.10649 (14)	0.0140 (4)
C8	0.1290 (3)	−0.01030 (15)	0.21725 (17)	0.0160 (4)
H8A	0.0377	−0.0387	0.2215	0.019*
C9	0.4310 (2)	0.15101 (17)	−0.04837 (15)	0.0187 (4)
H9A	0.5135	0.1049	−0.0524	0.022*
H9B	0.4755	0.2165	−0.0159	0.022*
C10	0.3281 (2)	0.17380 (15)	−0.15035 (15)	0.0157 (4)
C11	0.3731 (2)	0.15135 (16)	−0.23221 (15)	0.0179 (4)
H11A	0.4677	0.1201	−0.2251	0.021*
C12	0.2768 (2)	0.17560 (16)	−0.32396 (15)	0.0179 (4)
C13	0.1394 (2)	0.22057 (16)	−0.33922 (15)	0.0205 (4)
H13A	0.0766	0.2364	−0.4037	0.025*
C14	0.0949 (2)	0.24231 (17)	−0.25725 (16)	0.0209 (4)
H14A	0.0000	0.2733	−0.2652	0.025*
C15	0.1886 (2)	0.21895 (16)	−0.16387 (15)	0.0191 (4)
H15A	0.1569	0.2340	−0.1083	0.023*
C16	0.2665 (3)	−0.01102 (16)	0.40122 (16)	0.0181 (5)
H16A	0.3434	0.0378	0.4424	0.022*
C17	0.1208 (3)	0.00727 (17)	0.42384 (19)	0.0238 (5)
H17A	0.0852	0.0780	0.4042	0.036*
H17B	0.1375	−0.0014	0.4945	0.036*
H17C	0.0455	−0.0429	0.3874	0.036*
C18	0.3242 (3)	−0.1208 (2)	0.42492 (17)	0.0307 (5)
H18A	0.4155	−0.1299	0.4062	0.046*
H18B	0.2477	−0.1702	0.3883	0.046*
H18C	0.3466	−0.1333	0.4956	0.046*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.00955 (7)	0.01405 (7)	0.01116 (7)	−0.00130 (4)	0.00039 (5)	−0.00091 (4)
Cl1	0.0192 (3)	0.0674 (5)	0.0179 (3)	−0.0222 (3)	−0.0002 (2)	0.0010 (3)
Cl2	0.0140 (2)	0.0248 (3)	0.0274 (3)	0.0009 (2)	0.0023 (2)	−0.0114 (2)
F1	0.0371 (8)	0.0390 (8)	0.0154 (6)	0.0029 (6)	0.0115 (6)	−0.0034 (6)
N1	0.0135 (8)	0.0234 (9)	0.0147 (8)	−0.0018 (7)	0.0034 (7)	0.0004 (7)
N3	0.0122 (8)	0.0219 (9)	0.0140 (8)	−0.0012 (7)	0.0022 (7)	−0.0011 (7)
N6	0.0149 (8)	0.0232 (9)	0.0123 (8)	−0.0060 (7)	0.0008 (7)	0.0012 (7)
N7	0.0133 (9)	0.0159 (9)	0.0130 (9)	−0.0009 (6)	0.0022 (7)	−0.0001 (6)
N9	0.0141 (9)	0.0180 (9)	0.0112 (9)	−0.0013 (6)	0.0024 (7)	0.0007 (6)
C2	0.0112 (9)	0.0260 (12)	0.0174 (10)	−0.0028 (8)	0.0010 (8)	−0.0011 (9)
C4	0.0133 (9)	0.0137 (10)	0.0140 (10)	0.0016 (8)	0.0039 (8)	0.0006 (8)
C5	0.0124 (9)	0.0125 (10)	0.0145 (9)	0.0013 (8)	0.0015 (8)	−0.0010 (8)
C6	0.0128 (9)	0.0133 (10)	0.0148 (10)	0.0016 (8)	0.0026 (8)	−0.0006 (8)
C8	0.0125 (11)	0.0189 (11)	0.0155 (11)	−0.0032 (8)	0.0024 (9)	−0.0003 (8)
C9	0.0155 (10)	0.0247 (11)	0.0158 (10)	−0.0026 (9)	0.0046 (8)	0.0018 (9)
C10	0.0166 (10)	0.0139 (10)	0.0163 (10)	−0.0030 (8)	0.0046 (8)	0.0005 (8)
C11	0.0177 (10)	0.0170 (10)	0.0192 (10)	0.0007 (8)	0.0059 (8)	0.0010 (8)
C12	0.0247 (11)	0.0170 (10)	0.0138 (10)	−0.0026 (9)	0.0085 (9)	−0.0006 (8)
C13	0.0222 (11)	0.0191 (11)	0.0169 (10)	−0.0020 (9)	0.0009 (8)	0.0044 (8)
C14	0.0148 (10)	0.0200 (11)	0.0268 (11)	0.0022 (8)	0.0050 (9)	0.0051 (9)
C15	0.0214 (11)	0.0196 (11)	0.0187 (10)	0.0007 (9)	0.0098 (9)	0.0009 (9)
C16	0.0164 (11)	0.0283 (12)	0.0097 (10)	−0.0043 (8)	0.0039 (9)	−0.0014 (8)
C17	0.0232 (13)	0.0290 (13)	0.0227 (13)	−0.0019 (9)	0.0121 (10)	−0.0015 (9)
C18	0.0334 (13)	0.0408 (14)	0.0195 (11)	0.0122 (11)	0.0103 (10)	0.0117 (10)

Pt1—N7	2.0108 (18)	C9—H9A	0.9900
Pt1—N7ⁱ	2.0109 (18)	C9—H9B	0.9900
Pt1—Cl2	2.2940 (5)	C10—C15	1.390 (3)
Pt1—Cl2ⁱ	2.2940 (5)	C10—C11	1.390 (3)
Cl1—C2	1.748 (2)	C11—C12	1.380 (3)
F1—C12	1.366 (2)	C11—H11A	0.9500
N1—C2	1.324 (3)	C12—C13	1.368 (3)
N1—C6	1.348 (3)	C13—C14	1.387 (3)
N3—C2	1.317 (3)	C13—H13A	0.9500
N3—C4	1.349 (3)	C14—C15	1.386 (3)
N6—C6	1.333 (3)	C14—H14A	0.9500
N6—C9	1.453 (3)	C15—H15A	0.9500
N6—H6A	0.8800	C16—C18	1.513 (3)
N7—C8	1.323 (3)	C16—C17	1.516 (3)
N7—C5	1.390 (3)	C16—H16A	1.0000
N9—C8	1.350 (3)	C17—H17A	0.9800
N9—C4	1.372 (3)	C17—H17B	0.9800
N9—C16	1.485 (3)	C17—H17C	0.9800
C4—C5	1.382 (3)	C18—H18A	0.9800
C5—C6	1.412 (3)	C18—H18B	0.9800
C8—H8A	0.9500	C18—H18C	0.9800
C9—C10	1.508 (3)

N7—Pt1—N7ⁱ	180.0	H9A—C9—H9B	108.3
N7—Pt1—Cl2	89.91 (5)	C15—C10—C11	119.10 (19)
N7ⁱ—Pt1—Cl2	90.09 (5)	C15—C10—C9	120.70 (18)
N7—Pt1—Cl2ⁱ	90.09 (5)	C11—C10—C9	120.19 (18)
N7ⁱ—Pt1—Cl2ⁱ	89.91 (5)	C12—C11—C10	118.25 (19)
Cl2—Pt1—Cl2ⁱ	180.00 (3)	C12—C11—H11A	120.9
C2—N1—C6	117.27 (17)	C10—C11—H11A	120.9
C2—N3—C4	109.68 (17)	C13—C12—F1	118.13 (19)
C6—N6—C9	124.74 (17)	C13—C12—C11	123.80 (19)
C6—N6—H6A	117.6	F1—C12—C11	118.06 (19)
C9—N6—H6A	117.6	C12—C13—C14	117.65 (19)
C8—N7—C5	105.71 (18)	C12—C13—H13A	121.2
C8—N7—Pt1	124.49 (15)	C14—C13—H13A	121.2
C5—N7—Pt1	129.68 (14)	C15—C14—C13	120.2 (2)
C8—N9—C4	106.56 (18)	C15—C14—H14A	119.9
C8—N9—C16	127.83 (19)	C13—C14—H14A	119.9
C4—N9—C16	125.45 (18)	C14—C15—C10	121.01 (19)
N3—C2—N1	131.76 (19)	C14—C15—H15A	119.5
N3—C2—Cl1	114.12 (15)	C10—C15—H15A	119.5
N1—C2—Cl1	114.11 (15)	N9—C16—C18	109.15 (17)
N3—C4—N9	126.44 (18)	N9—C16—C17	110.76 (19)
N3—C4—C5	126.43 (18)	C18—C16—C17	112.39 (19)
N9—C4—C5	107.08 (17)	N9—C16—H16A	108.1
C4—C5—N7	108.25 (17)	C18—C16—H16A	108.1
C4—C5—C6	116.90 (17)	C17—C16—H16A	108.1
N7—C5—C6	134.64 (18)	C16—C17—H17A	109.5
N6—C6—N1	119.28 (18)	C16—C17—H17B	109.5
N6—C6—C5	122.78 (18)	H17A—C17—H17B	109.5
N1—C6—C5	117.92 (17)	C16—C17—H17C	109.5
N7—C8—N9	112.38 (19)	H17A—C17—H17C	109.5
N7—C8—H8A	123.8	H17B—C17—H17C	109.5
N9—C8—H8A	123.8	C16—C18—H18A	109.5
N6—C9—C10	109.24 (16)	C16—C18—H18B	109.5
N6—C9—H9A	109.8	H18A—C18—H18B	109.5
C10—C9—H9A	109.8	C16—C18—H18C	109.5
N6—C9—H9B	109.8	H18A—C18—H18C	109.5
C10—C9—H9B	109.8	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···Cl2ⁱ	0.88	2.53	3.222 (2)	136
C13—H13A···Cl2ⁱⁱ	0.95	2.86	3.492 (2)	125
C18—H18A···F1ⁱⁱⁱ	0.98	2.49	3.450 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯Cl2ⁱ	0.88	2.53	3.222 (2)	136
C13—H13A⋯Cl2ⁱⁱ	0.95	2.86	3.492 (2)	125
C18—H18A⋯F1ⁱⁱⁱ	0.98	2.49	3.450 (3)	166

Symmetry codes: (i) ; (ii) ; (iii) .

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