Home Physical Sciences Crystal structure of (N-benzylpropane-1,3-diamine-κ2N, N′)(2,2′-bipyridine-κ2N,N′)platinum(II) chloride, C20H24Cl2N4Pt
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Crystal structure of (N-benzylpropane-1,3-diamine-κ2N, N′)(2,2′-bipyridine-κ2N,N′)platinum(II) chloride, C20H24Cl2N4Pt

  • Tatsuto Kiwada EMAIL logo , Hiromu Katakasu and Akira Odani EMAIL logo
Published/Copyright: February 6, 2019

Abstract

C20H24Cl2N4Pt, monoclinic, P21/c (no. 14), a = 13.1119(7) Å, b = 13.5673(8) Å, c = 11.7167(5) Å, β = 99.714(7)°, V = 2054.43(19) Å3, Z = 4, Rgt(F) = 0.0233, wRref(F2) = 0.0516, T = 103 K.

CCDC no.: 1890692

The title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow block
Size:0.50 × 0.30 × 0.20 mm
Wavelength:Mo Kα radiation (0.71075 Å)
μ:7.08 mm−1
Diffractometer, scan mode:Rigaku R-AXIS RAPID, ω
θmax, completeness:27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:19454, 4699, 0.053
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3983
N(param)refined:244
Programs:Crystal Structure [1], SHELX [2], Mercury [3]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
Pt10.25871(2)0.00560(2)0.35292(2)0.01391(5)
Cl10.08614(7)0.02830(6)0.68034(6)0.02413(18)
Cl20.34219(7)0.16495(5)0.03469(6)0.02164(17)
N10.3780(2)−0.05265(17)0.2848(2)0.0161(5)
N20.3359(2)−0.06574(17)0.4950(2)0.0179(6)
N40.1994(2)0.08949(17)0.2101(2)0.0170(6)
H4A0.2540530.0901980.1600070.020*
N30.1381(2)0.05643(17)0.4266(2)0.0178(6)
H3A0.0785090.0313420.3859350.021*
H3B0.1451610.0316050.4997030.021*
C130.1848(3)0.1955(2)0.2423(3)0.0213(7)
H13B0.2512190.2206400.2852240.026*
H13A0.1676850.2346220.1702920.026*
C40.5437(3)−0.1296(2)0.3324(3)0.0230(7)
H40.596124−0.1578620.3888090.028*
C80.4674(3)−0.1468(2)0.6823(3)0.0231(7)
H60.513171−0.1727000.7468500.028*
C20.4787(3)−0.0844(2)0.1368(3)0.0220(7)
H20.485003−0.0818510.0573170.026*
C60.4285(3)−0.1035(2)0.4814(2)0.0164(6)
C10.3902(3)−0.0504(2)0.1728(3)0.0201(7)
H10.335915−0.0244710.1168210.024*
C50.4528(3)−0.0955(2)0.3634(2)0.0183(7)
C70.4950(3)−0.1457(2)0.5732(3)0.0206(7)
H50.558856−0.1735840.5612630.025*
C30.5576(3)−0.1219(2)0.2173(3)0.0261(8)
H30.620593−0.1423750.1947970.031*
C120.1021(3)0.2121(2)0.3146(3)0.0226(7)
H12A0.0360240.1849550.2731640.027*
H12B0.0926730.2839410.3235700.027*
C90.3729(3)−0.1098(2)0.6950(3)0.0237(7)
H70.351965−0.1112430.7687370.028*
C100.3073(3)−0.0702(2)0.6005(2)0.0217(7)
H80.241348−0.0459040.6101610.026*
C140.1036(3)0.0502(2)0.1350(3)0.0198(7)
H14B0.0789290.0983790.0730570.024*
H14A0.0483480.0417020.1823630.024*
C110.1259(3)0.1655(2)0.4337(3)0.0216(7)
H11B0.1903960.1943290.4768840.026*
H11A0.0691370.1805110.4770530.026*
C150.1243(3)−0.0479(2)0.0809(3)0.0190(7)
C200.1142(3)−0.1357(2)0.1383(3)0.0237(7)
H200.095163−0.1348270.2129810.028*
C160.1516(3)−0.0504(2)−0.0292(3)0.0238(7)
H160.1593380.009267−0.0692260.029*
C190.1320(3)−0.2255(2)0.0869(3)0.0290(8)
H190.126167−0.2853730.1273290.035*
C180.1581(3)−0.2275(3)−0.0224(3)0.0309(8)
H180.169451−0.288663−0.0576770.037*
C170.1675(3)−0.1403(2)−0.0800(3)0.0272(8)
H170.185139−0.141648−0.1553440.033*

Source of material

The 2,2′-bipyridine platinum(II) dichloride was synthesized according to the literature method with slightly modifications [4]. To a suspension of 2,2′-bipyridine platinum(II) dichloride (420 mg, 1.0 mmol) in water (20 mL), N-benzylpropane-1,3-diamine⋅2HCl (284 mg, 1.2 mmol), and sodium bicarbonate (159 mg, 1.5 mmol) were added. The mixture was stirred at 353 K for 2 h. The solution was filtered and the filtrate was concentrated under vacuum. Ethanol was added and white precipitate was removed by filtration. The filtrate was concentrated and then reprecipitated from ether/ethanol. Yield: 253 mg (43%). Single crystals suitable for crystal structure determination were obtained by vapor diffusion of diethyl ether into a ethanol solution of the product at 298 K. Elemental analysis, Found: C 41.13; H 4.11; N 9.47%. Calcd for [C20H24Cl2N4Pt]: C 40.96; H 4.13; N 9.55%. 1H NMR (D2O) δ: 8.73 (d, 1H), 8.39 (t, 1H), 8.34 (d, 1H), 8.25 (d, 1H), 8.18 (t, 1H), 7.85 (m, 2H), 7.81 (t, 1H), 7.75 (d, 1H), 7.39 (t, 1H), 7.22 (m, 3H), 4.52 (d, 1H), 3.99 (d, 1H), 3.32 (m, 2H), 3.19 (d, 1H), 2.99 (t, 1H), 2.28 (m, 2H).

Experimental details

Absorption corrections were applied by using multi-scan program. Hydrogen atoms were placed in calculated positions and included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C).

Comment

Platinum complexes have been used for cancer chemotherapy [5], [6]. The target of platinum complexes are nucleotides [7], [8], [9]. However, platinum complexes also affect the activities of proteins [10, 11] . We have demonstrated that platinum complexes with an aromatic heterocycle and N-arylmethylpropane-1,3-diamine exhibited cytotoxicities and inhibitory activities against cancer-associated proteins [12, 13] . As part of our studies in this area, we have synthesized the title complex, [Pt(C10H8N2)(C10H16N2)]Cl2. The synthesis and structure of an analogous (N-benzylethane-1,2-diamine)(2,2′-bipyridine) platinum(II) nitrate salt have been reported [14]. However, the title complex is a chloride salt and contains, in contrast to the literature known ones, a N-benzylpropane-1,3-diamine as ligand. It is known that a counter ion may affect structure and solubility of a complex salt. Also, solubility is important for clinical application. It is possible that the size of the Pt chelate ring also affects the structure of the platinum complex. Thus, we determined the structure of the title complex.

The asymmetric unit of the title structure consists of one dicationic platinum complex and two chloride counter anions (cf. the figure). The central platinum atom is chelated with N-benzylpropane-1,3-diamine and 2,2′-bipyridine. The centroid-centroid distance between the N1/C1—C5 ring and the C15—C20 ring is 4.657(2) Å. The Pt1—N4—C14—C15 torsion angle is −63.4(3)°. The C15—C20 aromatic ring is close to the N1/C1—C5 ring of 2,2′-bipyridine. The C15—C20 ring and the 2,2′-bipyridine ligand are not in the same plane, but are in a bowed configuration. Principally, platinum complexes have a square planar geometry [15, 16] . However, the title complex shows distortion from planarity. The r.m.s. deviation of the least-squares plane formed by Pt1, N1, N2, N3 and N4 is 0.075 Å. Furthermore, the propanediamine chain is tilted to 2,2′-bipyridine plane.

In the crystal, [Pt(C10H8N2)(C10H16N2)]2+ forms dimer through π–π interaction. Intermolecular π–π stacking interactions are observed between the 2,2′-bipyridine rings. The above mentioned dimer is composed of enantiomeric pair. The [Pt(C10H8N2)(C10H16N2)]2+ dimers are interlinked through a NH⋯Cl⋯HN hydrogen-bonding network.

Acknowledgements

We gratefully acknowledge support by Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT) (award No. 25288027).

References

1. Rigaku. Crystal Structure. Version 4.3., Rigaku Corporation, Tokyo, Japan (2018).Search in Google Scholar

2. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

3. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A.: Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures. J. Appl. Crystallogr. 41 (2008) 466–470.10.1107/S0021889807067908Search in Google Scholar

4. Newkome, G. R.; Theriot, K. J.; Fronczec, F. R.; Villar, B.: Synthesis and characterization of metalated and cyclometalated platinum(II) and platinum (IV) complexes of beta-diesters. Organometallics 8 (1989) 2513–2523.10.1021/om00113a003Search in Google Scholar

5. Wheate, N. J.; Walker, S.; Craig, G. E.; Oun, R.: The status of platinum anticancer drugs in the clinic and in clinical trials. Dalton. Trans. 39 (2010) 8113–8127.10.1039/c0dt00292eSearch in Google Scholar PubMed

6. Boulikas, T.; Vougiouka, M.: Recent clinical trials using cisplatin, carboplatin and their combination chemotherapy drugs. Oncol. Rep. 11 (2004) 559–595.10.3892/or.11.3.559Search in Google Scholar

7. Mansuri-Torshizi, H.; Ghadimy, S.; Akbarzadeh, N.: Synthesis, characterization, DNA binding and cytotoxic studies of platinum(II) and palladium(II) complexes of the 2,2′-bipyridine and an anion of 1,1-cyclobutanedicarboxylic acid. Chem. Pharm. Bull. 49 (2001) 1517–1520.10.1248/cpb.49.1517Search in Google Scholar PubMed

8. Takahara, P. M.; Rosenzweig, A. C.; Frederick, C. A.; Lippard, S. J.: Crystal structure of double stranded DNA containing the major adduct of the anticancer drug cisplatin. Nature 377 (1995) 649–652.10.1038/377649a0Search in Google Scholar PubMed

9. Howe-Grant, M.; Wu, K. C.; Bauer, W. R.; Lippard, S. J.: Binding of platinum and palladium metallointercalation reagents and antitumor drugs to closed and open DNAs. Biochemistry 15 (1976) 4339–4346.10.1021/bi00664a031Search in Google Scholar PubMed

10. Garbutcheon-Singh, K. B.; Myers, S.; Harper, B. W. J.; Ng, N. S.; Dong, Q.; Xie, C.; Aldrich-Wright, J. R.: The effects of 56MESS on mitochondrial and cytoskeletal proteins and the cell cycle in MDCK cells. Metallomics 5 (2013) 1061–1067.10.1039/c3mt00023kSearch in Google Scholar PubMed

11. Williams, D. S.; Caroll, P. J.; Meggers, E.: Platinum complex as a nanomolar protein kinase inhibitor. Inorg. Chem. 46 (2007) 2944–2946.10.1021/ic062055tSearch in Google Scholar PubMed

12. Igarashi, K.; Yamamoto, N.; Hayashi, K.; Takeuchi, A.; Miwa, S.; Odani, A.; Tsuchiya, H.: Effectiveness of two novel anionic and cationic platinum complexes in the treatment of osteosarcoma. Anticancer Agents Med. Chem. 15 (2015) 390–399.10.2174/1871520615666141216151547Search in Google Scholar PubMed

13. Odani, A.: Metal complexes and anticancer agents comprising same as active ingredient. Patent WO 2011125911 A1 (2011).Search in Google Scholar

14. Goto, M.; Matsumoto, T.; Sumimoto, M.; Kurosaki, H.: Intramolecular stacking of two aromatic rings in the platinum (II) coordination sphere: preparation, crystal structures, and 1H NMR spectra of bipyridine (N-arylmethyl-1,2-ethanediamine)platinum(II) nitrate. Bull. Chem. Soc. Jpn. 73 (2000) 97–105.10.1246/bcsj.73.97Search in Google Scholar

15. Suntharalingam, K.; White, A. J. P.; Vilar, R.: Synthesis, structural characterization, and quadruplex DNA binding studies of platinum(II)-terpyridine complexes. Inorg. Chem. 48 (2009) 9427–9435.10.1021/ic901319nSearch in Google Scholar PubMed

16. Koshiyama, T.; Kato, M.: [(1R,2R)-1,2-Diaminocyclohexane-κ2N,N′](α-diimine-κ2N, N′)platinum(II) bis(hexafluorophosphate), where α-diimine is 2,2′-bipyridine and 1,10-phenanthroline. Acta Crystallogr. C59 (2003) m446–m449.10.1107/S0108270103020869Search in Google Scholar

Received: 2018-11-29
Accepted: 2019-01-14
Published Online: 2019-02-06
Published in Print: 2019-03-26

©2019 Tatsuto Kiwada et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  61. Crystal structure of poly-[(μ2(carboxylatomethyl)((3-nitrophenyl)sulfonyl)amido-κ3N: O:O′)(μ2-4,4′-bipyridine-κ2N:N′)copper(II)], C18H14CuN4O6S
  62. Crystal structure of poly-[(μ2-(carboxylatomethyl)((3-nitrophenyl)sulfonyl)amido-κ3N:O:O′)(μ2-4,4′-bipyridine-κ2N:N′) nickel(II)], C18H14NiN4O6S
  63. Crystal structure of N-((3R,10S,13S,17S)-17-((S)-1-(dimethylamino)ethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-N-methylbenzamide, C31H48N2O
  64. The crystal structure of dichloroido(1,3-bis(2,6-dimethyl-phenyl)-1H-3l4-imidazol-2-yl)(2-methyl-4,5-dihydrooxazol-κN)palladium(IV)-water (1/1), C23H29Cl2N3O2Pd
  65. Crystal structure of catena-poly[dibromido-{μ2-1,5-dimethyl-2-phenyl-4-((pyridin-4-ylmethylene)amino)-1,2-dihydro-3H-pyrazol-3-one-κ2N:O}zinc(II)], C34H32Br4N8O2Zn2
  66. Crystal structure of diaqua-dichlorido-bis(μ2-2-(((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)dicobalt(II), C36H36Cl2N6O6Co2
  67. Crystal structure of catena-poly[diaqua-(μ2-1,2-bis(4-pyridinyl)ethyane-κ2N:N′)-(μ2–pyridazine-4,5-dicarboxylato-κ2O:O′)]dizinc(II) dihydrate, C12H12ZnN3O6
  68. The crystal structure of 2-(4-chloro-2,6-dinitrophenyl)-1-(4-chloro)diazene oxide, C12H6Cl2N4O5
  69. Crystal structure of 2-isopropylthioxanthone, C16H14OS
  70. Crystal structure of methyl 2-(4-(3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)phenyl)acetate, C19H17N5O2
  71. Crystal structure of 4,4-dimethyl-2-(trifluoromethyl)-4,5-dihydro-1H-imidazole, C6H9F3N2
  72. Crystal structure of N-methylanilinium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-sulfonate monohydrate, C22H21NO8S
  73. Crystal structure of methyl 4-acetoxybenzoate, C10H10O4
  74. Crystal structure of catena-poly[(bis(μ-1,1′-[(5-methoxy-2,4,6-trimethyl-1,3-phenylene)bis(methylene)]bis(1H-1,2,4-triazole)-κ2N:N′)-bis(isothiocyanato-κN)manganese(II)], C34H40MnN14O2S2
  75. Crystal structure of N-(2-methylphenyl)(propan-2-yloxy)carbothioamide, C11H15NOS
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