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Platinum antitumour agents, containing aromatic rings, which are used for targeting DNA in effective therapies for the treatment of cancer. We have syn­thesized the title metallocomplex with an aromatic ligand and determined its crystal structure. In many cases, complexes of platinum and other metals have a symmetrical structure. In contrast, the platinum(II) complex with pyridine and N-(9-anthracenylmeth­yl)-1,2-ethanedi­amine as ligands (systematic name: cis-{N-[(anthracen-9-yl)meth­yl]ethane-1,2-di­amine-κ2N,N′}­bis­(pyridine-κN)pla­ti­num(II) dinitrate), [Pt(C5H5N)2(C17H18N2)](NO3)2, is asymmetric. Of the two pyridine ligands, only one is π-stacked with anthracene, resulting in an asymmetric structure. Moreover, the angle of orientation of each pyridine ligand is variable. Further examination of the packing motif confirms an inter­molecular edge-to-face inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617014255/qs3062sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617014255/qs3062Isup2.hkl
Contains datablock I

CCDC reference: 1577766

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXT (Sheldrick, 2015a); molecular graphics: SHELXL2016 (Sheldrick, 2015b); software used to prepare material for publication: ORTEP-3 (Farrugia, 2012).

cis-{N-[(Anthracen-9-yl)methyl]ethane-1,2-diamine}bis(pyridine-κN)platinum(II) dinitrate top
Crystal data top
[Pt(C17H18N2)(C5H5N)2](NO3)2Z = 2
Mr = 727.64F(000) = 716
Triclinic, P1Dx = 1.808 Mg m3
a = 10.264 (2) ÅMo Kα radiation, λ = 0.7107 Å
b = 12.066 (3) ÅCell parameters from 4674 reflections
c = 13.382 (3) Åθ = 3.2–27.5°
α = 98.7061 (14)°µ = 5.30 mm1
β = 110.5915 (15)°T = 173 K
γ = 113.5911 (16)°Prism, colorless
V = 1336.8 (5) Å30.20 × 0.20 × 0.20 mm
Data collection top
Rigaku Saturn
diffractometer
5457 reflections with I > 2σ(I)
ω scansRint = 0.023
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2000)
θmax = 27.5°, θmin = 3.2°
Tmin = 0.636, Tmax = 1.000h = 1311
10468 measured reflectionsk = 1515
5837 independent reflectionsl = 1716
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.050 w = 1/[σ2(Fo2) + (0.0229P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
5837 reflectionsΔρmax = 1.85 e Å3
361 parametersΔρmin = 1.11 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pt10.05838 (2)0.20220 (2)0.20510 (2)0.01374 (4)
N10.2911 (3)0.3271 (2)0.25535 (19)0.0147 (5)
N20.1247 (3)0.1704 (2)0.3551 (2)0.0174 (5)
N30.0188 (3)0.2202 (2)0.04821 (19)0.0153 (5)
H3N0.0612080.2246070.0205140.018*
N40.1767 (3)0.0759 (2)0.1488 (2)0.0206 (5)
H4BN0.1884810.0027000.1501200.025*
H4AN0.2117290.1029050.1960480.025*
O10.1453 (3)0.1555 (2)0.06580 (17)0.0251 (5)
O20.1311 (3)0.1237 (2)0.23416 (19)0.0316 (5)
C140.0948 (3)0.4622 (3)0.1223 (2)0.0172 (6)
O30.0227 (3)0.1860 (2)0.1959 (2)0.0400 (6)
N60.5923 (3)0.1035 (3)0.2819 (2)0.0301 (6)
C150.2204 (3)0.5293 (3)0.0956 (2)0.0182 (6)
C260.0202 (4)0.4563 (3)0.2594 (3)0.0260 (7)
H260.1058250.3718880.2134170.031*
C90.1065 (4)0.1686 (3)0.5273 (3)0.0266 (7)
H90.0661140.1876550.5774870.032*
N50.0838 (3)0.1557 (2)0.1667 (2)0.0229 (5)
C20.5205 (3)0.5324 (3)0.3704 (3)0.0259 (7)
H20.5688460.6138260.4267120.031*
C10.3650 (3)0.4429 (3)0.3362 (2)0.0188 (6)
H10.3071550.4633410.3708330.023*
C60.2217 (3)0.1185 (3)0.3808 (2)0.0211 (6)
H60.2625720.1017400.3301850.025*
C210.3374 (4)0.7163 (3)0.2636 (3)0.0267 (7)
H210.4159900.8028940.3093820.032*
C120.1712 (3)0.0968 (3)0.0275 (2)0.0227 (6)
H12A0.1470400.0267060.0448580.027*
H12B0.2277920.1063560.0998430.027*
C100.0678 (3)0.1940 (3)0.4267 (2)0.0217 (6)
H100.0015560.2294600.4079100.026*
C80.2047 (4)0.1151 (3)0.5534 (3)0.0287 (7)
H80.2324530.0961780.6218080.034*
C170.3507 (4)0.5409 (3)0.0258 (3)0.0306 (7)
H170.3549790.5013220.0906890.037*
C220.2200 (4)0.6500 (3)0.2933 (3)0.0240 (7)
C40.5325 (4)0.3822 (3)0.2417 (3)0.0280 (7)
H40.5897540.3582300.2086960.034*
C50.3755 (3)0.2974 (3)0.2099 (2)0.0206 (6)
H50.3252410.2151610.1541580.025*
C200.3428 (3)0.6585 (3)0.1676 (3)0.0226 (6)
C70.2624 (4)0.0892 (3)0.4791 (3)0.0264 (7)
H70.3294710.0515780.4954590.032*
C110.2749 (3)0.0643 (3)0.0314 (3)0.0243 (7)
H11A0.3186300.1238270.0337270.029*
H11B0.3653370.0245400.0104300.029*
C130.0433 (3)0.3333 (3)0.0391 (2)0.0183 (6)
H13A0.1385520.3200980.0495040.022*
H13B0.0664660.3353620.0387640.022*
C160.2290 (4)0.4740 (3)0.0021 (3)0.0224 (6)
H160.1486080.3891840.0516820.027*
C270.0950 (3)0.5203 (3)0.2220 (2)0.0199 (6)
C250.0092 (4)0.5143 (4)0.3596 (3)0.0356 (8)
H250.0858070.4685270.3831910.043*
C190.4666 (4)0.7256 (3)0.1380 (3)0.0315 (8)
H190.5469680.8115830.1843560.038*
C240.1134 (5)0.6406 (4)0.4294 (3)0.0414 (9)
H240.1185720.6792290.4991140.050*
O40.6838 (4)0.0678 (3)0.3318 (3)0.0643 (9)
O50.6216 (5)0.1590 (3)0.2158 (3)0.0789 (12)
C230.2232 (4)0.7067 (3)0.3972 (3)0.0365 (8)
H230.3041340.7923880.4440660.044*
C180.4709 (4)0.6684 (4)0.0452 (3)0.0358 (8)
H180.5546940.7138450.0275240.043*
O60.4757 (3)0.0869 (3)0.2963 (3)0.0719 (10)
C30.6060 (4)0.5021 (3)0.3216 (3)0.0309 (7)
H30.7133730.5628790.3428390.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt10.01219 (6)0.01539 (6)0.01482 (6)0.00744 (5)0.00585 (4)0.00684 (4)
N10.0122 (11)0.0164 (11)0.0146 (11)0.0066 (9)0.0046 (9)0.0084 (9)
N20.0145 (12)0.0182 (11)0.0176 (12)0.0067 (10)0.0061 (10)0.0081 (10)
N30.0135 (12)0.0186 (11)0.0147 (11)0.0093 (10)0.0053 (9)0.0061 (9)
N40.0151 (12)0.0220 (12)0.0256 (13)0.0091 (10)0.0094 (11)0.0104 (11)
O10.0300 (12)0.0319 (12)0.0208 (11)0.0194 (10)0.0129 (10)0.0117 (9)
O20.0414 (14)0.0331 (12)0.0259 (12)0.0159 (11)0.0231 (11)0.0113 (10)
C140.0174 (14)0.0208 (13)0.0174 (14)0.0142 (12)0.0049 (11)0.0100 (11)
O30.0436 (15)0.0486 (15)0.0308 (13)0.0343 (13)0.0078 (11)0.0097 (12)
N60.0241 (15)0.0318 (15)0.0301 (15)0.0143 (13)0.0105 (12)0.0026 (12)
C150.0174 (14)0.0209 (14)0.0209 (14)0.0129 (12)0.0070 (12)0.0127 (12)
C260.0244 (17)0.0322 (16)0.0278 (17)0.0200 (14)0.0108 (13)0.0115 (14)
C90.0271 (17)0.0242 (15)0.0215 (16)0.0045 (13)0.0137 (14)0.0067 (13)
N50.0250 (14)0.0180 (12)0.0215 (13)0.0090 (11)0.0088 (11)0.0052 (10)
C20.0191 (16)0.0193 (14)0.0248 (16)0.0067 (13)0.0006 (13)0.0019 (12)
C10.0193 (15)0.0217 (14)0.0150 (14)0.0109 (12)0.0060 (12)0.0070 (11)
C60.0192 (15)0.0243 (14)0.0206 (15)0.0127 (13)0.0068 (12)0.0095 (12)
C210.0230 (16)0.0204 (14)0.0240 (16)0.0107 (13)0.0009 (13)0.0040 (12)
C120.0177 (15)0.0201 (14)0.0201 (15)0.0056 (12)0.0041 (12)0.0032 (12)
C100.0194 (15)0.0238 (14)0.0224 (15)0.0090 (13)0.0117 (13)0.0084 (12)
C80.0264 (17)0.0291 (16)0.0175 (15)0.0042 (14)0.0055 (13)0.0125 (13)
C170.0320 (19)0.0411 (19)0.0328 (18)0.0232 (17)0.0200 (16)0.0200 (16)
C220.0266 (17)0.0258 (15)0.0200 (15)0.0181 (14)0.0053 (13)0.0065 (13)
C40.0223 (17)0.0318 (17)0.0350 (18)0.0139 (14)0.0167 (15)0.0134 (15)
C50.0202 (15)0.0221 (14)0.0199 (15)0.0098 (13)0.0101 (12)0.0069 (12)
C200.0171 (15)0.0256 (15)0.0234 (15)0.0118 (13)0.0039 (12)0.0129 (13)
C70.0208 (16)0.0257 (15)0.0268 (16)0.0110 (13)0.0042 (13)0.0119 (13)
C110.0109 (14)0.0238 (15)0.0265 (16)0.0038 (12)0.0021 (12)0.0087 (13)
C130.0171 (15)0.0211 (14)0.0189 (14)0.0122 (12)0.0058 (12)0.0100 (12)
C160.0256 (16)0.0265 (15)0.0240 (16)0.0169 (14)0.0130 (13)0.0150 (13)
C270.0221 (16)0.0247 (15)0.0192 (14)0.0180 (13)0.0071 (12)0.0104 (12)
C250.040 (2)0.051 (2)0.036 (2)0.0317 (19)0.0231 (17)0.0211 (18)
C190.0181 (16)0.0307 (17)0.0340 (19)0.0057 (14)0.0049 (14)0.0165 (15)
C240.054 (3)0.054 (2)0.0252 (18)0.036 (2)0.0185 (18)0.0067 (17)
O40.0558 (19)0.082 (2)0.066 (2)0.0550 (19)0.0147 (16)0.0256 (18)
O50.150 (4)0.092 (3)0.090 (3)0.097 (3)0.095 (3)0.064 (2)
C230.045 (2)0.0348 (18)0.0271 (18)0.0251 (17)0.0100 (16)0.0028 (15)
C180.0232 (18)0.049 (2)0.042 (2)0.0162 (17)0.0179 (16)0.0277 (18)
O60.0392 (18)0.086 (2)0.093 (3)0.0303 (18)0.0407 (18)0.009 (2)
C30.0155 (16)0.0252 (16)0.0385 (19)0.0024 (13)0.0090 (14)0.0066 (15)
Geometric parameters (Å, º) top
Pt1—N12.028 (2)C2—H20.9500
Pt1—N22.030 (2)C1—H10.9500
Pt1—N32.047 (2)C6—C71.379 (4)
Pt1—N42.035 (2)C6—H60.9500
N1—C11.348 (3)C21—C221.383 (4)
C1—C21.371 (4)C21—H210.9500
C2—C31.385 (4)C12—H12A0.9900
N4—C111.487 (4)C12—H12B0.9900
C11—C121.502 (4)C10—H100.9500
N3—C121.501 (3)C8—C71.380 (5)
N3—C131.497 (3)C8—H80.9500
C13—C141.506 (4)C17—C161.364 (4)
C14—C151.421 (4)C17—C181.416 (5)
C15—C161.424 (4)C17—H170.9500
C19—C201.434 (4)C22—C231.437 (4)
C20—C211.395 (4)C22—C271.444 (4)
N1—C51.342 (3)C4—C51.375 (4)
N2—C101.337 (4)C4—C31.377 (4)
N2—C61.351 (3)C4—H40.9500
N3—H3N1.0000C5—H50.9500
N4—H4BN0.9100C7—H70.9500
N4—H4AN0.9100C11—H11A0.9900
O1—N51.274 (3)C11—H11B0.9900
O2—N51.246 (3)C13—H13A0.9900
C14—C271.409 (4)C13—H13B0.9900
O3—N51.243 (3)C16—H160.9500
N6—O61.221 (3)C25—C241.410 (5)
N6—O41.218 (4)C25—H250.9500
N6—O51.236 (4)C19—C181.349 (5)
C15—C201.436 (4)C19—H190.9500
C26—C251.359 (4)C24—C231.349 (5)
C26—C271.431 (4)C24—H240.9500
C26—H260.9500C23—H230.9500
C9—C81.377 (5)C18—H180.9500
C9—C101.382 (4)C3—H30.9500
C9—H90.9500
N1—Pt1—N288.76 (9)N2—C10—C9122.1 (3)
N1—Pt1—N4177.95 (8)N2—C10—H10119.0
N2—Pt1—N493.10 (9)C9—C10—H10119.0
N1—Pt1—N394.14 (9)C9—C8—C7119.2 (3)
N2—Pt1—N3175.87 (8)C9—C8—H8120.4
N4—Pt1—N383.96 (10)C7—C8—H8120.4
C5—N1—C1118.3 (2)C16—C17—C18120.9 (3)
C5—N1—Pt1121.50 (19)C16—C17—H17119.6
C1—N1—Pt1120.16 (19)C18—C17—H17119.6
C10—N2—C6119.1 (3)C21—C22—C23120.9 (3)
C10—N2—Pt1121.09 (19)C21—C22—C27120.3 (3)
C6—N2—Pt1119.7 (2)C23—C22—C27118.8 (3)
C13—N3—C12110.5 (2)C5—C4—C3119.4 (3)
C13—N3—Pt1117.71 (17)C5—C4—H4120.3
C12—N3—Pt1105.66 (17)C3—C4—H4120.3
C13—N3—H3N107.5N1—C5—C4122.1 (3)
C12—N3—H3N107.5N1—C5—H5119.0
Pt1—N3—H3N107.5C4—C5—H5119.0
C11—N4—Pt1111.34 (18)C21—C20—C19121.6 (3)
C11—N4—H4BN109.4C21—C20—C15119.4 (3)
Pt1—N4—H4BN109.4C19—C20—C15118.9 (3)
C11—N4—H4AN109.4C6—C7—C8119.4 (3)
Pt1—N4—H4AN109.4C6—C7—H7120.3
H4BN—N4—H4AN108.0C8—C7—H7120.3
C27—C14—C15119.9 (3)N4—C11—C12108.6 (2)
C27—C14—C13120.7 (3)N4—C11—H11A110.0
C15—C14—C13119.3 (2)C12—C11—H11A110.0
O6—N6—O4122.1 (4)N4—C11—H11B110.0
O6—N6—O5120.2 (3)C12—C11—H11B110.0
O4—N6—O5117.7 (3)H11A—C11—H11B108.3
C14—C15—C16122.4 (3)N3—C13—C14115.5 (2)
C14—C15—C20119.8 (3)N3—C13—H13A108.4
C16—C15—C20117.8 (3)C14—C13—H13A108.4
C25—C26—C27121.1 (3)N3—C13—H13B108.4
C25—C26—H26119.4C14—C13—H13B108.4
C27—C26—H26119.4H13A—C13—H13B107.5
C8—C9—C10118.9 (3)C17—C16—C15121.1 (3)
C8—C9—H9120.6C17—C16—H16119.4
C10—C9—H9120.6C15—C16—H16119.4
O3—N5—O2121.6 (3)C14—C27—C26123.5 (3)
O3—N5—O1119.5 (3)C14—C27—C22119.2 (3)
O2—N5—O1118.9 (2)C26—C27—C22117.3 (3)
C1—C2—C3119.0 (3)C26—C25—C24121.5 (3)
C1—C2—H2120.5C26—C25—H25119.2
C3—C2—H2120.5C24—C25—H25119.2
N1—C1—C2122.4 (3)C18—C19—C20121.0 (3)
N1—C1—H1118.8C18—C19—H19119.5
C2—C1—H1118.8C20—C19—H19119.5
N2—C6—C7121.3 (3)C23—C24—C25119.9 (3)
N2—C6—H6119.3C23—C24—H24120.0
C7—C6—H6119.3C25—C24—H24120.0
C22—C21—C20121.4 (3)C24—C23—C22121.3 (3)
C22—C21—H21119.3C24—C23—H23119.4
C20—C21—H21119.3C22—C23—H23119.4
N3—C12—C11109.2 (2)C19—C18—C17120.2 (3)
N3—C12—H12A109.8C19—C18—H18119.9
C11—C12—H12A109.8C17—C18—H18119.9
N3—C12—H12B109.8C4—C3—C2118.8 (3)
C11—C12—H12B109.8C4—C3—H3120.6
H12A—C12—H12B108.3C2—C3—H3120.6
N3—Pt1—N1—C1110.2 (2)Pt1—N4—C11—C1226.1 (3)
Pt1—N3—C13—C1450.8 (3)N3—C12—C11—N448.5 (3)
N4—Pt1—N2—C1060.1 (3)C12—N3—C13—C14172.3 (2)
C27—C14—C15—C16178.1 (3)Pt1—N3—C13—C1450.8 (3)
C13—C14—C15—C166.2 (4)C27—C14—C13—N398.9 (3)
C27—C14—C15—C203.0 (4)C15—C14—C13—N385.4 (3)
C13—C14—C15—C20172.7 (2)C18—C17—C16—C151.2 (5)
C5—N1—C1—C22.4 (4)C14—C15—C16—C17179.8 (3)
Pt1—N1—C1—C2177.8 (2)C20—C15—C16—C170.9 (4)
C3—C2—C1—N11.1 (5)C15—C14—C27—C26175.4 (2)
C10—N2—C6—C70.2 (4)C13—C14—C27—C269.0 (4)
Pt1—N2—C6—C7176.5 (2)C15—C14—C27—C222.6 (4)
C13—N3—C12—C1181.7 (3)C13—C14—C27—C22173.0 (2)
Pt1—N3—C12—C1146.7 (2)C25—C26—C27—C14176.2 (3)
C6—N2—C10—C90.9 (4)C25—C26—C27—C221.8 (4)
Pt1—N2—C10—C9177.5 (2)C21—C22—C27—C140.4 (4)
C8—C9—C10—N21.2 (4)C23—C22—C27—C14177.5 (3)
C10—C9—C8—C70.4 (5)C21—C22—C27—C26178.5 (3)
C20—C21—C22—C23174.9 (3)C23—C22—C27—C260.6 (4)
C20—C21—C22—C273.0 (4)C27—C26—C25—C241.6 (5)
C1—N1—C5—C41.5 (4)C21—C20—C19—C18179.7 (3)
Pt1—N1—C5—C4178.7 (2)C15—C20—C19—C181.1 (4)
C3—C4—C5—N10.7 (5)C26—C25—C24—C230.1 (5)
C22—C21—C20—C19178.3 (3)C25—C24—C23—C221.2 (5)
C22—C21—C20—C152.5 (4)C21—C22—C23—C24177.0 (3)
C14—C15—C20—C210.5 (4)C27—C22—C23—C240.9 (5)
C16—C15—C20—C21179.4 (3)C20—C19—C18—C170.9 (5)
C14—C15—C20—C19178.7 (3)C16—C17—C18—C190.2 (5)
C16—C15—C20—C190.2 (4)C5—C4—C3—C21.9 (5)
N2—C6—C7—C80.9 (5)C1—C2—C3—C41.1 (5)
C9—C8—C7—C60.6 (5)
 

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