Asymmetric structure of cis-[N-(9-an­thra­cenyl­meth­yl)-1,2-ethanedi­amine]dipyridineplatinum(II) dinitrate

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.

Computing details

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

Crystal data

[Pt(C17H18N2)(C5H5N)2](NO3)2	Z = 2
Mr = 727.64	F(000) = 716
Triclinic, P1	Dx = 1.808 Mg m^−3
a = 10.264 (2) Å	Mo Kα radiation, λ = 0.7107 Å
b = 12.066 (3) Å	Cell parameters from 4674 reflections
c = 13.382 (3) Å	θ = 3.2–27.5°
α = 98.7061 (14)°	µ = 5.30 mm^−1
β = 110.5915 (15)°	T = 173 K
γ = 113.5911 (16)°	Prism, colorless
V = 1336.8 (5) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn diffractometer	5457 reflections with I > 2σ(I)
ω scans	Rint = 0.023
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	θmax = 27.5°, θmin = 3.2°
Tmin = 0.636, Tmax = 1.000	h = −13→11
10468 measured reflections	k = −15→15
5837 independent reflections	l = −17→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.021	H-atom parameters constrained
wR(F^2) = 0.050	w = 1/[σ^2(Fo^2) + (0.0229P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
5837 reflections	Δρmax = 1.85 e Å^−3
361 parameters	Δρmin = −1.11 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Pt1	0.05838 (2)	0.20220 (2)	0.20510 (2)	0.01374 (4)
N1	0.2911 (3)	0.3271 (2)	0.25535 (19)	0.0147 (5)
N2	0.1247 (3)	0.1704 (2)	0.3551 (2)	0.0174 (5)
N3	−0.0188 (3)	0.2202 (2)	0.04821 (19)	0.0153 (5)
H3N	0.061208	0.224607	0.020514	0.018*
N4	−0.1767 (3)	0.0759 (2)	0.1488 (2)	0.0206 (5)
H4BN	−0.188481	−0.002700	0.150120	0.025*
H4AN	−0.211729	0.102905	0.196048	0.025*
O1	0.1453 (3)	0.1555 (2)	−0.06580 (17)	0.0251 (5)
O2	0.1311 (3)	0.1237 (2)	−0.23416 (19)	0.0316 (5)
C14	0.0948 (3)	0.4622 (3)	0.1223 (2)	0.0172 (6)
O3	−0.0227 (3)	0.1860 (2)	−0.1959 (2)	0.0400 (6)
N6	0.5923 (3)	0.1035 (3)	0.2819 (2)	0.0301 (6)
C15	0.2204 (3)	0.5293 (3)	0.0956 (2)	0.0182 (6)
C26	−0.0202 (4)	0.4563 (3)	0.2594 (3)	0.0260 (7)
H26	−0.105825	0.371888	0.213417	0.031*
C9	0.1065 (4)	0.1686 (3)	0.5273 (3)	0.0266 (7)
H9	0.066114	0.187655	0.577487	0.032*
N5	0.0838 (3)	0.1557 (2)	−0.1667 (2)	0.0229 (5)
C2	0.5205 (3)	0.5324 (3)	0.3704 (3)	0.0259 (7)
H2	0.568846	0.613826	0.426712	0.031*
C1	0.3650 (3)	0.4429 (3)	0.3362 (2)	0.0188 (6)
H1	0.307155	0.463341	0.370833	0.023*
C6	0.2217 (3)	0.1185 (3)	0.3808 (2)	0.0211 (6)
H6	0.262572	0.101740	0.330185	0.025*
C21	0.3374 (4)	0.7163 (3)	0.2636 (3)	0.0267 (7)
H21	0.415990	0.802894	0.309382	0.032*
C12	−0.1712 (3)	0.0968 (3)	−0.0275 (2)	0.0227 (6)
H12A	−0.147040	0.026706	−0.044858	0.027*
H12B	−0.227792	0.106356	−0.099843	0.027*
C10	0.0678 (3)	0.1940 (3)	0.4267 (2)	0.0217 (6)
H10	−0.001556	0.229460	0.407910	0.026*
C8	0.2047 (4)	0.1151 (3)	0.5534 (3)	0.0287 (7)
H8	0.232453	0.096178	0.621808	0.034*
C17	0.3507 (4)	0.5409 (3)	−0.0258 (3)	0.0306 (7)
H17	0.354979	0.501322	−0.090689	0.037*
C22	0.2200 (4)	0.6500 (3)	0.2933 (3)	0.0240 (7)
C4	0.5325 (4)	0.3822 (3)	0.2417 (3)	0.0280 (7)
H4	0.589754	0.358230	0.208696	0.034*
C5	0.3755 (3)	0.2974 (3)	0.2099 (2)	0.0206 (6)
H5	0.325241	0.215161	0.154158	0.025*
C20	0.3428 (3)	0.6585 (3)	0.1676 (3)	0.0226 (6)
C7	0.2624 (4)	0.0892 (3)	0.4791 (3)	0.0264 (7)
H7	0.329471	0.051578	0.495459	0.032*
C11	−0.2749 (3)	0.0643 (3)	0.0314 (3)	0.0243 (7)
H11A	−0.318630	0.123827	0.033727	0.029*
H11B	−0.365337	−0.024540	−0.010430	0.029*
C13	−0.0433 (3)	0.3333 (3)	0.0391 (2)	0.0183 (6)
H13A	−0.138552	0.320098	0.049504	0.022*
H13B	−0.066466	0.335362	−0.038764	0.022*
C16	0.2290 (4)	0.4740 (3)	−0.0021 (3)	0.0224 (6)
H16	0.148608	0.389184	−0.051682	0.027*
C27	0.0950 (3)	0.5203 (3)	0.2220 (2)	0.0199 (6)
C25	−0.0092 (4)	0.5143 (4)	0.3596 (3)	0.0356 (8)
H25	−0.085807	0.468527	0.383191	0.043*
C19	0.4666 (4)	0.7256 (3)	0.1380 (3)	0.0315 (8)
H19	0.546968	0.811583	0.184356	0.038*
C24	0.1134 (5)	0.6406 (4)	0.4294 (3)	0.0414 (9)
H24	0.118572	0.679229	0.499114	0.050*
O4	0.6838 (4)	0.0678 (3)	0.3318 (3)	0.0643 (9)
O5	0.6216 (5)	0.1590 (3)	0.2158 (3)	0.0789 (12)
C23	0.2232 (4)	0.7067 (3)	0.3972 (3)	0.0365 (8)
H23	0.304134	0.792388	0.444066	0.044*
C18	0.4709 (4)	0.6684 (4)	0.0452 (3)	0.0358 (8)
H18	0.554694	0.713845	0.027524	0.043*
O6	0.4757 (3)	0.0869 (3)	0.2963 (3)	0.0719 (10)
C3	0.6060 (4)	0.5021 (3)	0.3216 (3)	0.0309 (7)
H3	0.713373	0.562879	0.342839	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.01219 (6)	0.01539 (6)	0.01482 (6)	0.00744 (5)	0.00585 (4)	0.00684 (4)
N1	0.0122 (11)	0.0164 (11)	0.0146 (11)	0.0066 (9)	0.0046 (9)	0.0084 (9)
N2	0.0145 (12)	0.0182 (11)	0.0176 (12)	0.0067 (10)	0.0061 (10)	0.0081 (10)
N3	0.0135 (12)	0.0186 (11)	0.0147 (11)	0.0093 (10)	0.0053 (9)	0.0061 (9)
N4	0.0151 (12)	0.0220 (12)	0.0256 (13)	0.0091 (10)	0.0094 (11)	0.0104 (11)
O1	0.0300 (12)	0.0319 (12)	0.0208 (11)	0.0194 (10)	0.0129 (10)	0.0117 (9)
O2	0.0414 (14)	0.0331 (12)	0.0259 (12)	0.0159 (11)	0.0231 (11)	0.0113 (10)
C14	0.0174 (14)	0.0208 (13)	0.0174 (14)	0.0142 (12)	0.0049 (11)	0.0100 (11)
O3	0.0436 (15)	0.0486 (15)	0.0308 (13)	0.0343 (13)	0.0078 (11)	0.0097 (12)
N6	0.0241 (15)	0.0318 (15)	0.0301 (15)	0.0143 (13)	0.0105 (12)	0.0026 (12)
C15	0.0174 (14)	0.0209 (14)	0.0209 (14)	0.0129 (12)	0.0070 (12)	0.0127 (12)
C26	0.0244 (17)	0.0322 (16)	0.0278 (17)	0.0200 (14)	0.0108 (13)	0.0115 (14)
C9	0.0271 (17)	0.0242 (15)	0.0215 (16)	0.0045 (13)	0.0137 (14)	0.0067 (13)
N5	0.0250 (14)	0.0180 (12)	0.0215 (13)	0.0090 (11)	0.0088 (11)	0.0052 (10)
C2	0.0191 (16)	0.0193 (14)	0.0248 (16)	0.0067 (13)	0.0006 (13)	0.0019 (12)
C1	0.0193 (15)	0.0217 (14)	0.0150 (14)	0.0109 (12)	0.0060 (12)	0.0070 (11)
C6	0.0192 (15)	0.0243 (14)	0.0206 (15)	0.0127 (13)	0.0068 (12)	0.0095 (12)
C21	0.0230 (16)	0.0204 (14)	0.0240 (16)	0.0107 (13)	−0.0009 (13)	0.0040 (12)
C12	0.0177 (15)	0.0201 (14)	0.0201 (15)	0.0056 (12)	0.0041 (12)	0.0032 (12)
C10	0.0194 (15)	0.0238 (14)	0.0224 (15)	0.0090 (13)	0.0117 (13)	0.0084 (12)
C8	0.0264 (17)	0.0291 (16)	0.0175 (15)	0.0042 (14)	0.0055 (13)	0.0125 (13)
C17	0.0320 (19)	0.0411 (19)	0.0328 (18)	0.0232 (17)	0.0200 (16)	0.0200 (16)
C22	0.0266 (17)	0.0258 (15)	0.0200 (15)	0.0181 (14)	0.0053 (13)	0.0065 (13)
C4	0.0223 (17)	0.0318 (17)	0.0350 (18)	0.0139 (14)	0.0167 (15)	0.0134 (15)
C5	0.0202 (15)	0.0221 (14)	0.0199 (15)	0.0098 (13)	0.0101 (12)	0.0069 (12)
C20	0.0171 (15)	0.0256 (15)	0.0234 (15)	0.0118 (13)	0.0039 (12)	0.0129 (13)
C7	0.0208 (16)	0.0257 (15)	0.0268 (16)	0.0110 (13)	0.0042 (13)	0.0119 (13)
C11	0.0109 (14)	0.0238 (15)	0.0265 (16)	0.0038 (12)	0.0021 (12)	0.0087 (13)
C13	0.0171 (15)	0.0211 (14)	0.0189 (14)	0.0122 (12)	0.0058 (12)	0.0100 (12)
C16	0.0256 (16)	0.0265 (15)	0.0240 (16)	0.0169 (14)	0.0130 (13)	0.0150 (13)
C27	0.0221 (16)	0.0247 (15)	0.0192 (14)	0.0180 (13)	0.0071 (12)	0.0104 (12)
C25	0.040 (2)	0.051 (2)	0.036 (2)	0.0317 (19)	0.0231 (17)	0.0211 (18)
C19	0.0181 (16)	0.0307 (17)	0.0340 (19)	0.0057 (14)	0.0049 (14)	0.0165 (15)
C24	0.054 (3)	0.054 (2)	0.0252 (18)	0.036 (2)	0.0185 (18)	0.0067 (17)
O4	0.0558 (19)	0.082 (2)	0.066 (2)	0.0550 (19)	0.0147 (16)	0.0256 (18)
O5	0.150 (4)	0.092 (3)	0.090 (3)	0.097 (3)	0.095 (3)	0.064 (2)
C23	0.045 (2)	0.0348 (18)	0.0271 (18)	0.0251 (17)	0.0100 (16)	0.0028 (15)
C18	0.0232 (18)	0.049 (2)	0.042 (2)	0.0162 (17)	0.0179 (16)	0.0277 (18)
O6	0.0392 (18)	0.086 (2)	0.093 (3)	0.0303 (18)	0.0407 (18)	0.009 (2)
C3	0.0155 (16)	0.0252 (16)	0.0385 (19)	0.0024 (13)	0.0090 (14)	0.0066 (15)

Geometric parameters (Å, º)

Pt1—N1	2.028 (2)	C2—H2	0.9500
Pt1—N2	2.030 (2)	C1—H1	0.9500
Pt1—N3	2.047 (2)	C6—C7	1.379 (4)
Pt1—N4	2.035 (2)	C6—H6	0.9500
N1—C1	1.348 (3)	C21—C22	1.383 (4)
C1—C2	1.371 (4)	C21—H21	0.9500
C2—C3	1.385 (4)	C12—H12A	0.9900
N4—C11	1.487 (4)	C12—H12B	0.9900
C11—C12	1.502 (4)	C10—H10	0.9500
N3—C12	1.501 (3)	C8—C7	1.380 (5)
N3—C13	1.497 (3)	C8—H8	0.9500
C13—C14	1.506 (4)	C17—C16	1.364 (4)
C14—C15	1.421 (4)	C17—C18	1.416 (5)
C15—C16	1.424 (4)	C17—H17	0.9500
C19—C20	1.434 (4)	C22—C23	1.437 (4)
C20—C21	1.395 (4)	C22—C27	1.444 (4)
N1—C5	1.342 (3)	C4—C5	1.375 (4)
N2—C10	1.337 (4)	C4—C3	1.377 (4)
N2—C6	1.351 (3)	C4—H4	0.9500
N3—H3N	1.0000	C5—H5	0.9500
N4—H4BN	0.9100	C7—H7	0.9500
N4—H4AN	0.9100	C11—H11A	0.9900
O1—N5	1.274 (3)	C11—H11B	0.9900
O2—N5	1.246 (3)	C13—H13A	0.9900
C14—C27	1.409 (4)	C13—H13B	0.9900
O3—N5	1.243 (3)	C16—H16	0.9500
N6—O6	1.221 (3)	C25—C24	1.410 (5)
N6—O4	1.218 (4)	C25—H25	0.9500
N6—O5	1.236 (4)	C19—C18	1.349 (5)
C15—C20	1.436 (4)	C19—H19	0.9500
C26—C25	1.359 (4)	C24—C23	1.349 (5)
C26—C27	1.431 (4)	C24—H24	0.9500
C26—H26	0.9500	C23—H23	0.9500
C9—C8	1.377 (5)	C18—H18	0.9500
C9—C10	1.382 (4)	C3—H3	0.9500
C9—H9	0.9500
N1—Pt1—N2	88.76 (9)	N2—C10—C9	122.1 (3)
N1—Pt1—N4	177.95 (8)	N2—C10—H10	119.0
N2—Pt1—N4	93.10 (9)	C9—C10—H10	119.0
N1—Pt1—N3	94.14 (9)	C9—C8—C7	119.2 (3)
N2—Pt1—N3	175.87 (8)	C9—C8—H8	120.4
N4—Pt1—N3	83.96 (10)	C7—C8—H8	120.4
C5—N1—C1	118.3 (2)	C16—C17—C18	120.9 (3)
C5—N1—Pt1	121.50 (19)	C16—C17—H17	119.6
C1—N1—Pt1	120.16 (19)	C18—C17—H17	119.6
C10—N2—C6	119.1 (3)	C21—C22—C23	120.9 (3)
C10—N2—Pt1	121.09 (19)	C21—C22—C27	120.3 (3)
C6—N2—Pt1	119.7 (2)	C23—C22—C27	118.8 (3)
C13—N3—C12	110.5 (2)	C5—C4—C3	119.4 (3)
C13—N3—Pt1	117.71 (17)	C5—C4—H4	120.3
C12—N3—Pt1	105.66 (17)	C3—C4—H4	120.3
C13—N3—H3N	107.5	N1—C5—C4	122.1 (3)
C12—N3—H3N	107.5	N1—C5—H5	119.0
Pt1—N3—H3N	107.5	C4—C5—H5	119.0
C11—N4—Pt1	111.34 (18)	C21—C20—C19	121.6 (3)
C11—N4—H4BN	109.4	C21—C20—C15	119.4 (3)
Pt1—N4—H4BN	109.4	C19—C20—C15	118.9 (3)
C11—N4—H4AN	109.4	C6—C7—C8	119.4 (3)
Pt1—N4—H4AN	109.4	C6—C7—H7	120.3
H4BN—N4—H4AN	108.0	C8—C7—H7	120.3
C27—C14—C15	119.9 (3)	N4—C11—C12	108.6 (2)
C27—C14—C13	120.7 (3)	N4—C11—H11A	110.0
C15—C14—C13	119.3 (2)	C12—C11—H11A	110.0
O6—N6—O4	122.1 (4)	N4—C11—H11B	110.0
O6—N6—O5	120.2 (3)	C12—C11—H11B	110.0
O4—N6—O5	117.7 (3)	H11A—C11—H11B	108.3
C14—C15—C16	122.4 (3)	N3—C13—C14	115.5 (2)
C14—C15—C20	119.8 (3)	N3—C13—H13A	108.4
C16—C15—C20	117.8 (3)	C14—C13—H13A	108.4
C25—C26—C27	121.1 (3)	N3—C13—H13B	108.4
C25—C26—H26	119.4	C14—C13—H13B	108.4
C27—C26—H26	119.4	H13A—C13—H13B	107.5
C8—C9—C10	118.9 (3)	C17—C16—C15	121.1 (3)
C8—C9—H9	120.6	C17—C16—H16	119.4
C10—C9—H9	120.6	C15—C16—H16	119.4
O3—N5—O2	121.6 (3)	C14—C27—C26	123.5 (3)
O3—N5—O1	119.5 (3)	C14—C27—C22	119.2 (3)
O2—N5—O1	118.9 (2)	C26—C27—C22	117.3 (3)
C1—C2—C3	119.0 (3)	C26—C25—C24	121.5 (3)
C1—C2—H2	120.5	C26—C25—H25	119.2
C3—C2—H2	120.5	C24—C25—H25	119.2
N1—C1—C2	122.4 (3)	C18—C19—C20	121.0 (3)
N1—C1—H1	118.8	C18—C19—H19	119.5
C2—C1—H1	118.8	C20—C19—H19	119.5
N2—C6—C7	121.3 (3)	C23—C24—C25	119.9 (3)
N2—C6—H6	119.3	C23—C24—H24	120.0
C7—C6—H6	119.3	C25—C24—H24	120.0
C22—C21—C20	121.4 (3)	C24—C23—C22	121.3 (3)
C22—C21—H21	119.3	C24—C23—H23	119.4
C20—C21—H21	119.3	C22—C23—H23	119.4
N3—C12—C11	109.2 (2)	C19—C18—C17	120.2 (3)
N3—C12—H12A	109.8	C19—C18—H18	119.9
C11—C12—H12A	109.8	C17—C18—H18	119.9
N3—C12—H12B	109.8	C4—C3—C2	118.8 (3)
C11—C12—H12B	109.8	C4—C3—H3	120.6
H12A—C12—H12B	108.3	C2—C3—H3	120.6
N3—Pt1—N1—C1	110.2 (2)	Pt1—N4—C11—C12	26.1 (3)
Pt1—N3—C13—C14	50.8 (3)	N3—C12—C11—N4	−48.5 (3)
N4—Pt1—N2—C10	−60.1 (3)	C12—N3—C13—C14	172.3 (2)
C27—C14—C15—C16	178.1 (3)	Pt1—N3—C13—C14	50.8 (3)
C13—C14—C15—C16	−6.2 (4)	C27—C14—C13—N3	−98.9 (3)
C27—C14—C15—C20	−3.0 (4)	C15—C14—C13—N3	85.4 (3)
C13—C14—C15—C20	172.7 (2)	C18—C17—C16—C15	−1.2 (5)
C5—N1—C1—C2	2.4 (4)	C14—C15—C16—C17	179.8 (3)
Pt1—N1—C1—C2	−177.8 (2)	C20—C15—C16—C17	0.9 (4)
C3—C2—C1—N1	−1.1 (5)	C15—C14—C27—C26	−175.4 (2)
C10—N2—C6—C7	0.2 (4)	C13—C14—C27—C26	9.0 (4)
Pt1—N2—C6—C7	−176.5 (2)	C15—C14—C27—C22	2.6 (4)
C13—N3—C12—C11	−81.7 (3)	C13—C14—C27—C22	−173.0 (2)
Pt1—N3—C12—C11	46.7 (2)	C25—C26—C27—C14	176.2 (3)
C6—N2—C10—C9	0.9 (4)	C25—C26—C27—C22	−1.8 (4)
Pt1—N2—C10—C9	177.5 (2)	C21—C22—C27—C14	0.4 (4)
C8—C9—C10—N2	−1.2 (4)	C23—C22—C27—C14	−177.5 (3)
C10—C9—C8—C7	0.4 (5)	C21—C22—C27—C26	178.5 (3)
C20—C21—C22—C23	174.9 (3)	C23—C22—C27—C26	0.6 (4)
C20—C21—C22—C27	−3.0 (4)	C27—C26—C25—C24	1.6 (5)
C1—N1—C5—C4	−1.5 (4)	C21—C20—C19—C18	179.7 (3)
Pt1—N1—C5—C4	178.7 (2)	C15—C20—C19—C18	−1.1 (4)
C3—C4—C5—N1	−0.7 (5)	C26—C25—C24—C23	−0.1 (5)
C22—C21—C20—C19	−178.3 (3)	C25—C24—C23—C22	−1.2 (5)
C22—C21—C20—C15	2.5 (4)	C21—C22—C23—C24	−177.0 (3)
C14—C15—C20—C21	0.5 (4)	C27—C22—C23—C24	0.9 (5)
C16—C15—C20—C21	179.4 (3)	C20—C19—C18—C17	0.9 (5)
C14—C15—C20—C19	−178.7 (3)	C16—C17—C18—C19	0.2 (5)
C16—C15—C20—C19	0.2 (4)	C5—C4—C3—C2	1.9 (5)
N2—C6—C7—C8	−0.9 (5)	C1—C2—C3—C4	−1.1 (5)
C9—C8—C7—C6	0.6 (5)