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Five new platinum(II) complexes bearing a eugenol and a quinoline derivative, namely [η2-4-allyl-2-meth­oxy-1-(propoxycarbonyl­meth­oxy)benzene]-trans-di­chlorido­(quinoline-κN)platinum(II), [PtCl2(C15H20O4)(C9H7N)], (2), {η2-4-allyl-2-meth­oxy-1-[(propan-2-yl­oxy)carbonyl­meth­oxy]benzene}-trans-di­chlorido­(quino­line-κN)platinum(II), [PtCl2(C15H19O4)(C9H7N)], (3), [η2-4-allyl-2-meth­oxy-1-(propoxycarbonyl­meth­oxy)benzene]­chlorido­(quinolin-8-olato-κ2N,O)platinum(II), [Pt(C9H6NO)Cl(C15H20O4)], (4), {η2-4-allyl-2-meth­oxy-1-[(propan-2-yl­oxy)car­bonyl­meth­oxy]benzene}­chlorido­(quinolin-8-olato-κ2N,O)platinum(II), [Pt(C9H6NO)Cl(C15H20O4)], (5), and [η2-4-allyl-2-meth­oxy-1-(propoxycarbonyl­meth­oxy)benzene]­chlorido­(quinolin-2-carboxyl­ato-κ2N,O)platinum(II), [Pt(C10H6NO2)Cl(C15H20O4)], (6), have been synthesized and fully characterized spectroscopically. A single-crystal X-ray diffraction study was carried out for complexes (2) and (4)–(6). PrEug [or 4-allyl-2-meth­oxy-1-(prop­oxycarbonyl­meth­oxy)benzene] in (2), (4) and (6), and iPrEug (the propan-2-yl­oxy analogue of PrEug) in (3) and (5) coordinate with PtII at the ethyl­enic double bond of the allyl group. In (2)–(6), the donor N atom of the amine group occupies a trans position with respect to the double bond. A comparison of the IC50 values of 0.38–29.23 µM for (2)–(6) with cisplatin, as well as other platinum(II) complexes, indicates an excellent in vitro cytotoxicity against the KB, LU, Hep-G2 and MCF-7 cancer cell lines, with the highest cytotoxic effect (IC50 = 0.38–1.99 µM) being for complexes (4) and (5) bearing a quinolin-8-olate ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618015978/ly3081sup1.cif
Contains datablocks chi29, chi30, chi9, chi33, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015978/ly3081chi30sup2.hkl
Contains datablock chi30

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015978/ly3081chi9sup3.hkl
Contains datablock chi9

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618015978/ly3081sup4.pdf
ESI-MS and NMR spectra

CCDC references: 1878366; 1878365; 1878364; 1878363

Computing details top

For all structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

[η2-4-Allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]-trans-dichlorido(quinoline-κN)platinum(II) (chi29) top
Crystal data top
[PtCl2(C15H20O4)(C9H7N)]Z = 2
Mr = 659.45F(000) = 644
Triclinic, P1Dx = 1.845 Mg m3
a = 8.1252 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.7042 (4) ÅCell parameters from 9524 reflections
c = 13.7340 (5) Åθ = 3.1–28.7°
α = 65.864 (4)°µ = 6.17 mm1
β = 84.716 (3)°T = 100 K
γ = 88.191 (3)°Needle, yellow
V = 1186.82 (9) Å30.35 × 0.1 × 0.1 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Eos detector
4867 independent reflections
Radiation source: SuperNova (Mo) X-ray Source4458 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.036
Detector resolution: 15.9631 pixels mm-1θmax = 26.4°, θmin = 2.9°
ω scansh = 1010
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1414
Tmin = 0.432, Tmax = 1.000l = 1617
19752 measured reflections
Refinement top
Refinement on F214 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0079P)2 + 5.6087P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
4867 reflectionsΔρmax = 3.21 e Å3
337 parametersΔρmin = 1.79 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*/UeqOcc. (<1)
Pt1A0.7798 (3)1.14396 (15)0.16089 (7)0.0218 (2)0.656 (8)
Pt1B0.8263 (6)1.1211 (3)0.15616 (15)0.0265 (4)0.344 (8)
Cl2A0.5445 (3)1.2493 (3)0.1821 (2)0.0266 (6)0.656 (8)
Cl2B0.5661 (6)1.1993 (8)0.1688 (4)0.0363 (13)0.344 (8)
Cl3A1.0244 (5)1.0451 (3)0.1445 (2)0.0277 (6)0.656 (8)
Cl3B1.0943 (11)1.0535 (7)0.1458 (5)0.0387 (15)0.344 (8)
N40.8817 (5)1.1787 (4)0.2779 (3)0.0304 (9)
C50.9845 (6)1.2744 (4)0.2488 (4)0.0270 (10)
H51.0176311.3171370.1746240.032*
C61.0480 (6)1.3173 (5)0.3183 (4)0.0291 (11)
H61.1213581.3870690.2928500.035*
C70.9996 (6)1.2538 (5)0.4266 (4)0.0331 (12)
H71.0381011.2805910.4771290.040*
C80.8923 (5)1.1485 (4)0.4616 (4)0.0220 (9)
C90.8457 (6)1.0762 (5)0.5707 (4)0.0329 (12)
H90.8865441.0981490.6234830.039*
C100.7439 (6)0.9763 (5)0.6016 (4)0.0360 (12)
H100.7118270.9291030.6753530.043*
C110.6863 (6)0.9429 (5)0.5240 (4)0.0292 (11)
H110.6144780.8724480.5469560.035*
C120.7277 (5)1.0061 (4)0.4171 (4)0.0263 (10)
H120.6877040.9803870.3663330.032*
C130.8345 (6)1.1133 (5)0.3841 (4)0.0266 (10)
C14A0.7271 (13)1.1640 (9)0.0050 (8)0.027 (2)0.656 (8)
H14A0.8183301.1504430.0373820.033*0.656 (8)
H14B0.6995291.2466560.0028970.033*0.656 (8)
C14B0.783 (3)1.1440 (12)0.0069 (16)0.025 (5)0.344 (8)
H14C0.6824051.1839800.0331080.030*0.344 (8)
H14D0.8832221.1903070.0277530.030*0.344 (8)
C15A0.6335 (8)1.0627 (6)0.0787 (5)0.0219 (17)0.656 (8)
H15A0.5140991.0848170.0836410.026*0.656 (8)
C15B0.7818 (15)1.0182 (12)0.0618 (10)0.030 (4)0.344 (8)
H15B0.8853280.9769090.0477010.036*0.344 (8)
C160.6538 (8)0.9333 (5)0.1026 (4)0.0433 (15)
H16A0.7642960.9222150.0707630.052*0.656 (8)
H16B0.5710230.9090660.0657430.052*0.656 (8)
H16C0.6581210.8829980.0593400.052*0.344 (8)
H16D0.5498570.9815380.0890990.052*0.344 (8)
C170.6386 (7)0.8423 (5)0.2189 (4)0.0303 (11)
C180.7735 (6)0.7702 (4)0.2630 (4)0.0263 (10)
H180.8739130.7786170.2193320.032*
C190.7647 (6)0.6864 (4)0.3692 (4)0.0247 (10)
C200.6174 (6)0.6750 (4)0.4348 (4)0.0259 (10)
C210.4818 (6)0.7449 (5)0.3906 (4)0.0306 (11)
H210.3805010.7358330.4336310.037*
C220.4930 (7)0.8286 (5)0.2830 (4)0.0347 (12)
H220.3993860.8767300.2536420.042*
O230.8917 (4)0.6111 (3)0.4178 (3)0.0280 (7)
C241.0443 (6)0.6212 (5)0.3527 (4)0.0331 (12)
H24A1.0244730.6009990.2922030.050*
H24B1.1248050.5625390.3958780.050*
H24C1.0875520.7068050.3258340.050*
O250.6212 (4)0.5923 (3)0.5400 (3)0.0294 (8)
C260.4797 (6)0.5859 (5)0.6092 (4)0.0271 (10)
H26A0.3854820.5509280.5891580.032*
H26B0.4496640.6707250.6040020.032*
C270.5177 (6)0.5029 (4)0.7221 (4)0.0269 (10)
O280.6508 (4)0.4610 (3)0.7501 (3)0.0340 (8)
O290.3804 (4)0.4862 (3)0.7874 (3)0.0296 (8)
C300.3997 (6)0.4167 (5)0.9005 (4)0.0313 (11)
H30A0.4970990.4478840.9208480.038*
H30B0.4154430.3266220.9170350.038*
C310.2440 (6)0.4356 (5)0.9611 (4)0.0334 (12)
H31A0.2298950.5261730.9430800.040*
H31B0.2557330.3929591.0389690.040*
C320.0907 (6)0.3855 (5)0.9357 (4)0.0331 (12)
H32A0.0764370.4293070.8591050.050*
H32B0.0064170.3991170.9773840.050*
H32C0.1034430.2956260.9541580.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt1A0.0224 (5)0.0218 (4)0.02258 (19)0.0050 (3)0.0097 (2)0.00915 (19)
Pt1B0.0303 (10)0.0276 (6)0.0235 (4)0.0092 (6)0.0126 (5)0.0109 (4)
Cl2A0.0234 (10)0.0243 (13)0.0346 (11)0.0062 (9)0.0088 (8)0.0136 (10)
Cl2B0.034 (2)0.040 (3)0.035 (2)0.010 (2)0.0070 (17)0.015 (2)
Cl3A0.0237 (15)0.0344 (12)0.0284 (11)0.0061 (13)0.0057 (12)0.0161 (9)
Cl3B0.034 (4)0.053 (3)0.036 (2)0.012 (3)0.010 (3)0.024 (2)
N40.027 (2)0.033 (2)0.031 (2)0.0013 (18)0.0066 (18)0.0131 (19)
C50.025 (2)0.025 (3)0.028 (2)0.004 (2)0.001 (2)0.008 (2)
C60.027 (3)0.026 (3)0.038 (3)0.003 (2)0.008 (2)0.016 (2)
C70.028 (3)0.036 (3)0.044 (3)0.009 (2)0.009 (2)0.024 (3)
C80.016 (2)0.026 (2)0.026 (2)0.0102 (18)0.0037 (18)0.014 (2)
C90.030 (3)0.038 (3)0.026 (3)0.014 (2)0.000 (2)0.011 (2)
C100.031 (3)0.038 (3)0.032 (3)0.013 (2)0.003 (2)0.009 (2)
C110.019 (2)0.027 (3)0.036 (3)0.006 (2)0.002 (2)0.008 (2)
C120.019 (2)0.027 (3)0.029 (2)0.0057 (19)0.0062 (19)0.007 (2)
C130.021 (2)0.031 (3)0.027 (2)0.013 (2)0.0087 (19)0.010 (2)
C14A0.035 (6)0.035 (5)0.015 (4)0.001 (4)0.000 (4)0.013 (4)
C14B0.028 (8)0.032 (8)0.013 (7)0.010 (6)0.001 (6)0.007 (6)
C15A0.022 (4)0.024 (4)0.022 (3)0.000 (3)0.011 (3)0.009 (3)
C15B0.035 (7)0.038 (7)0.022 (6)0.003 (5)0.008 (5)0.017 (5)
C160.078 (4)0.025 (3)0.027 (3)0.005 (3)0.020 (3)0.006 (2)
C170.043 (3)0.021 (3)0.028 (3)0.003 (2)0.011 (2)0.008 (2)
C180.033 (3)0.021 (2)0.024 (2)0.000 (2)0.002 (2)0.010 (2)
C190.027 (2)0.021 (2)0.027 (2)0.0047 (19)0.0043 (19)0.010 (2)
C200.023 (2)0.021 (2)0.030 (3)0.0009 (19)0.0007 (19)0.008 (2)
C210.024 (2)0.023 (3)0.041 (3)0.004 (2)0.003 (2)0.009 (2)
C220.035 (3)0.026 (3)0.045 (3)0.008 (2)0.017 (2)0.014 (2)
O230.0241 (17)0.0315 (19)0.0235 (17)0.0103 (14)0.0027 (13)0.0079 (15)
C240.026 (3)0.040 (3)0.028 (3)0.006 (2)0.006 (2)0.011 (2)
O250.0275 (18)0.0244 (18)0.0228 (17)0.0054 (14)0.0111 (14)0.0009 (14)
C260.019 (2)0.024 (3)0.034 (3)0.0021 (19)0.0087 (19)0.010 (2)
C270.027 (3)0.019 (2)0.033 (3)0.004 (2)0.007 (2)0.010 (2)
O280.0217 (18)0.036 (2)0.035 (2)0.0053 (15)0.0056 (15)0.0076 (16)
O290.0236 (17)0.037 (2)0.0259 (17)0.0019 (15)0.0049 (14)0.0126 (15)
C300.024 (2)0.037 (3)0.029 (3)0.005 (2)0.001 (2)0.011 (2)
C310.025 (3)0.044 (3)0.030 (3)0.001 (2)0.006 (2)0.015 (2)
C320.031 (3)0.034 (3)0.032 (3)0.001 (2)0.005 (2)0.013 (2)
Geometric parameters (Å, º) top
PT1Aa—Cl2A2.303 (2)C12—C131.437 (7)
PT1Bb—Cl2B2.298 (5)C16—H16A0.9900
PT1Aa—Cl3A2.307 (3)C16—H16B0.9900
PT1Bb—Cl3B2.305 (6)C16—H16C0.9900
PT1Aa—N42.058 (4)C16—H16D0.9900
PT1Bb—N42.129 (5)C16—C171.510 (7)
PT1Aa—C14A2.139 (11)C17—C181.388 (7)
C14Aa—H14A0.9500C17—C221.381 (8)
C14Aa—H14B0.9500C18—H180.9500
PT1Bb—C14B2.20 (2)C18—C191.382 (6)
C14Bb—H14C0.9500C19—C201.406 (7)
C14Bb—H14D0.9500C19—O231.369 (5)
C14Aa—C15A1.394 (9)C20—C211.382 (7)
PT1Aa—C15A2.188 (6)C20—O251.374 (6)
C15Aa—H15A1.0000C21—H210.9500
PT1Bb—C15B2.157 (13)C21—C221.396 (7)
C14Bb—C15B1.386 (11)C22—H220.9500
C15Bb—H15B1.0000O23—C241.438 (5)
C15Bb—C161.373 (10)C24—H24A0.9800
C15Aa—C161.420 (8)C24—H24B0.9800
N4—C51.320 (6)C24—H24C0.9800
N4—C131.365 (6)O25—C261.406 (5)
C5—H50.9500C26—H26A0.9900
C5—C61.389 (7)C26—H26B0.9900
C6—H60.9500C26—C271.510 (7)
C6—C71.388 (7)C27—O281.203 (6)
C7—H70.9500C27—O291.332 (6)
C7—C81.419 (7)O29—C301.450 (6)
C8—C91.409 (7)C30—H30A0.9900
C8—C131.408 (6)C30—H30B0.9900
C9—H90.9500C30—C311.511 (6)
C9—C101.350 (8)C31—H31A0.9900
C10—H100.9500C31—H31B0.9900
C10—C111.398 (7)C31—C321.521 (7)
C11—H110.9500C32—H32A0.9800
C11—C121.361 (7)C32—H32B0.9800
C12—H120.9500C32—H32C0.9800
C14Aa—C15Aa—Pt1A69.3 (6)C15Bb—C16—H16D107.1
C15Aa—C14Aa—Pt1A73.1 (5)H16Cb—C16—H16D106.8
C5—N4—Pt1A118.8 (3)C15Aa—C16—C17117.9 (5)
C5—N4—Pt1B116.7 (3)C15Bb—C16—C17121.0 (7)
C5—N4—C13119.0 (4)C18—C17—C16119.7 (5)
C13—N4—Pt1A121.9 (3)C22—C17—C16121.6 (5)
C13—N4—Pt1B123.7 (3)C22—C17—C18118.7 (5)
N4—C5—H5117.5C17—C18—H18119.3
C14Bb—C15Bb—Pt1B73.4 (11)C19—C18—C17121.4 (5)
C15Bb—C14Bb—Pt1B69.6 (10)C19—C18—H18119.3
C15Aa—PT1Aa—Cl2A87.0 (2)C18—C19—C20119.6 (4)
C14Aa—PT1Aa—Cl2A92.7 (3)O23—C19—C18124.7 (4)
C15Bb—PT1Bb—Cl2B99.5 (5)O23—C19—C20115.8 (4)
C14Bb—PT1Bb—Cl2B87.8 (5)C21—C20—C19119.2 (4)
C15Aa—PT1Aa—Cl3A96.6 (2)O25—C20—C19115.7 (4)
CL2Aa—PT1Aa—Cl3A176.37 (10)O25—C20—C21125.1 (4)
C14Aa—PT1Aa—Cl3A90.0 (3)C20—C21—H21119.9
CL2Bb—PT1Bb—Cl3B176.1 (2)C20—C21—C22120.3 (5)
C14Bb—PT1Bb—Cl3B94.2 (5)C22—C21—H21119.9
C15Bb—PT1Bb—Cl3B84.1 (5)C17—C22—C21120.8 (5)
C15Aa—C14Aa—H14A120.0C17—C22—H22119.6
PT1Aa—C14Aa—H14A115.0C21—C22—H22119.6
H14Aa—C14Aa—H14B120.0C19—O23—C24117.0 (4)
C15Aa—C14Aa—H14B120.0O23—C24—H24A109.5
PT1Aa—C14Aa—H14B82.4N4—PT1Aa—Cl2A90.11 (14)
C15Bb—PT1Bb—C14B37.0 (4)N4—PT1Bb—Cl2B86.73 (18)
C15Bb—C14Bb—H14C120.0N4—PT1Aa—Cl3A86.51 (14)
PT1Bb—C14Bb—H14C116.1N4—PT1Bb—Cl3B90.1 (2)
PT1Bb—C14Bb—H14D84.8N4—PT1Aa—C14A159.7 (3)
C15Bb—C14Bb—H14D120.0N4—PT1Bb—C14B156.6 (4)
N4—C5—C6125.1 (5)N4—PT1Aa—C15A162.7 (2)
C6—C5—H5117.5N4—PT1Bb—C15B166.1 (4)
C5—C6—H6121.5C16—C15Aa—Pt1A117.7 (4)
C7—C6—C5117.0 (5)C16—C15Bb—Pt1B115.1 (8)
C7—C6—H6121.5C16—C15Bb—C14B130.5 (14)
C6—C7—H7120.1C16—C15Aa—H15A111.4
C6—C7—C8119.7 (5)C16—C15Bb—H15B110.6
C8—C7—H7120.1O23—C24—H24B109.5
C9—C8—C7122.4 (5)O23—C24—H24C109.5
C13—C8—C7118.5 (4)H24A—C24—H24B109.5
C13—C8—C9119.0 (5)H24A—C24—H24C109.5
C8—C9—H9119.5H24B—C24—H24C109.5
C10—C9—C8121.1 (5)C20—O25—C26116.9 (4)
C10—C9—H9119.5O25—C26—H26A110.1
C9—C10—H10120.3O25—C26—H26B110.1
C9—C10—C11119.4 (5)O25—C26—C27108.2 (4)
C11—C10—H10120.3H26A—C26—H26B108.4
C10—C11—H11118.4C27—C26—H26A110.1
C12—C11—C10123.3 (5)C27—C26—H26B110.1
C12—C11—H11118.4O28—C27—C26126.1 (4)
C11—C12—H12121.3O28—C27—O29124.9 (5)
C11—C12—C13117.4 (5)O29—C27—C26109.0 (4)
C13—C12—H12121.3C27—O29—C30115.7 (4)
N4—C13—C8120.6 (5)O29—C30—H30A110.3
N4—C13—C12119.5 (4)O29—C30—H30B110.3
C8—C13—C12119.9 (4)O29—C30—C31107.1 (4)
C17—C16—H16A107.8H30A—C30—H30B108.6
C17—C16—H16B107.8C31—C30—H30A110.3
C17—C16—H16C107.1C31—C30—H30B110.3
C17—C16—H16D107.1C30—C31—H31A109.1
H14Cb—C14Bb—H14D120.0C30—C31—H31B109.1
C14Aa—PT1Aa—C15A37.6 (3)C30—C31—C32112.6 (4)
C14Aa—C15Aa—H15A111.4H31A—C31—H31B107.8
PT1Aa—C15Aa—H15A111.4C32—C31—H31A109.1
C14Bb—C15Bb—H15B110.6C32—C31—H31B109.1
PT1Bb—C15Bb—H15B110.6C31—C32—H32A109.5
C14Aa—C15Aa—C16128.8 (7)C31—C32—H32B109.5
C15Aa—C16—H16A107.8C31—C32—H32C109.5
C15Aa—C16—H16B107.8H32A—C32—H32B109.5
H16Aa—C16—H16B107.2H32A—C32—H32C109.5
C15Bb—C16—H16C107.1H32B—C32—H32C109.5
PT1Aa—N4—C5—C6172.5 (4)C10—C11—C12—C130.9 (7)
PT1Bb—N4—C5—C6173.3 (4)C11—C12—C13—N4179.0 (4)
PT1Aa—N4—C13—C8172.7 (3)C11—C12—C13—C80.3 (7)
PT1Bb—C14Bb—C15Bb—C16109.1 (16)C13—N4—C5—C61.5 (8)
PT1Bb—N4—C13—C8172.2 (4)C13—C8—C9—C101.6 (7)
PT1Aa—N4—C13—C128.6 (6)C16—C17—C18—C19179.7 (4)
PT1Bb—N4—C13—C126.4 (6)C16—C17—C22—C21179.4 (5)
C15Bb—C16—C17—C1851.0 (10)C17—C18—C19—C201.1 (7)
PT1Aa—C14Aa—C15Aa—C16109.6 (7)C17—C18—C19—O23179.1 (4)
PT1Aa—C15Aa—C16—C1751.4 (7)C18—C17—C22—C210.7 (7)
C14Bb—C15Bb—C16—C17136.9 (16)C18—C19—C20—C212.3 (7)
C14Aa—C15Aa—C16—C17136.3 (9)C18—C19—C20—O25178.1 (4)
PT1Bb—C15Bb—C16—C1747.8 (11)C18—C19—O23—C240.1 (7)
C15Aa—C16—C17—C18117.4 (6)C19—C20—C21—C222.1 (7)
N4—C5—C6—C70.3 (8)C19—C20—O25—C26175.4 (4)
C5—N4—C13—C81.0 (7)C20—C19—O23—C24179.7 (4)
C5—N4—C13—C12177.6 (4)C20—C21—C22—C170.6 (8)
C5—C6—C7—C81.2 (7)C20—O25—C26—C27172.9 (4)
C6—C7—C8—C9176.6 (5)C21—C20—O25—C265.0 (7)
C6—C7—C8—C131.5 (7)C22—C17—C18—C190.4 (7)
C7—C8—C9—C10179.7 (5)O23—C19—C20—C21177.8 (4)
C7—C8—C13—N40.4 (7)O23—C19—C20—O251.8 (6)
C7—C8—C13—C12179.1 (4)O25—C20—C21—C22178.4 (5)
C8—C9—C10—C111.1 (7)O25—C26—C27—O287.9 (7)
C9—C8—C13—N4177.8 (4)O25—C26—C27—O29174.2 (4)
C9—C8—C13—C120.9 (6)C26—C27—O29—C30175.1 (4)
C9—C10—C11—C120.2 (8)C27—O29—C30—C31166.3 (4)
C15Bb—C16—C17—C22129.1 (9)O28—C27—O29—C302.9 (7)
C15Aa—C16—C17—C2262.7 (7)O29—C30—C31—C3261.8 (6)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of ring C17–C22.
D—H···AD—HH···AD···AD—H···A
C6—H6···O28ii0.952.473.404 (7)169
C7—H7···O23ii0.952.393.324 (7)168
C24—H24B···O23iiii0.982.533.287 (6)134
C12—H12···Cg10.952.933.732 (6)142
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+2, y+1, z+1.
[η2-4-Allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-8-olato-κ2N,O)platinum(II) (chi30) top
Crystal data top
[Pt(C9H6NO)Cl(C15H20O4)]Z = 2
Mr = 639.00F(000) = 624
Triclinic, P1Dx = 1.900 Mg m3
a = 8.3447 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.9191 (4) ÅCell parameters from 12015 reflections
c = 12.9315 (5) Åθ = 3.0–29.0°
α = 63.296 (4)°µ = 6.44 mm1
β = 84.618 (3)°T = 100 K
γ = 76.484 (3)°Block, orange
V = 1117.09 (7) Å30.25 × 0.25 × 0.1 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Eos detector
4564 independent reflections
Radiation source: SuperNova (Mo) X-ray Source4417 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.029
Detector resolution: 15.9631 pixels mm-1θmax = 26.4°, θmin = 2.8°
ω scansh = 1010
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1414
Tmin = 0.411, Tmax = 1.000l = 1616
18255 measured reflections
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.048 w = 1/[σ2(Fo2) + (0.0163P)2 + 2.8225P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
4564 reflectionsΔρmax = 2.18 e Å3
291 parametersΔρmin = 1.45 e Å3
0 restraints
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
Pt10.04044 (2)0.99699 (2)0.32891 (2)0.01151 (5)
Cl130.16523 (10)1.14992 (8)0.18856 (7)0.01867 (17)
O120.0616 (3)0.8637 (2)0.4578 (2)0.0154 (5)
O230.2621 (3)0.5145 (2)0.3564 (2)0.0176 (5)
O250.2664 (3)0.5075 (2)0.1596 (2)0.0146 (5)
O280.4923 (3)0.3181 (3)0.1420 (2)0.0255 (6)
O290.3771 (3)0.3538 (2)0.02330 (19)0.0153 (5)
N20.2441 (3)0.9061 (2)0.4345 (2)0.0112 (5)
C30.3926 (4)0.9321 (3)0.4188 (3)0.0146 (7)
H30.41231.00590.35220.017*
C40.5220 (4)0.8532 (3)0.4986 (3)0.0154 (7)
H40.62740.87430.48590.018*
C50.4963 (4)0.7459 (3)0.5946 (3)0.0136 (7)
H50.58370.69240.64850.016*
C60.3385 (4)0.7147 (3)0.6136 (3)0.0123 (6)
C70.2995 (4)0.6068 (3)0.7088 (3)0.0151 (7)
H70.38120.54800.76550.018*
C80.1415 (4)0.5875 (3)0.7187 (3)0.0179 (7)
H80.11560.51420.78300.022*
C90.0163 (4)0.6730 (3)0.6365 (3)0.0167 (7)
H90.09170.65700.64650.020*
C100.0502 (4)0.7797 (3)0.5419 (3)0.0125 (6)
C110.2137 (4)0.7999 (3)0.5310 (3)0.0112 (6)
C140.1965 (4)1.1023 (3)0.2518 (3)0.0168 (7)
H14A0.28151.08500.30470.020*
H14B0.15401.17460.23270.020*
C150.1322 (4)1.0206 (3)0.2011 (3)0.0145 (7)
H150.09791.06430.12090.017*
C160.1942 (4)0.9026 (3)0.2278 (3)0.0160 (7)
H16A0.29440.92800.18020.019*
H16B0.22670.86540.31000.019*
C170.0716 (4)0.7992 (3)0.2064 (3)0.0136 (7)
C180.0381 (4)0.7055 (3)0.2943 (3)0.0144 (7)
H180.03580.70700.36730.017*
C190.1504 (4)0.6104 (3)0.2758 (3)0.0132 (7)
C200.1528 (4)0.6070 (3)0.1684 (3)0.0116 (6)
C210.0445 (4)0.6995 (3)0.0812 (3)0.0140 (7)
H210.04520.69760.00850.017*
C220.0659 (4)0.7957 (3)0.1008 (3)0.0144 (7)
H220.13850.86020.04020.017*
C240.2638 (5)0.5115 (4)0.4676 (3)0.0289 (9)
H24A0.34600.43670.51730.043*
H24B0.15470.50540.50220.043*
H24C0.29190.59020.45980.043*
C260.2514 (4)0.4874 (3)0.0616 (3)0.0146 (7)
H26A0.26010.56580.01020.018*
H26B0.14290.46730.06110.018*
C270.3883 (4)0.3763 (3)0.0677 (3)0.0134 (7)
C300.5000 (5)0.2451 (3)0.0251 (3)0.0227 (8)
H30A0.47330.16320.03310.027*
H30B0.61050.24870.00650.027*
C310.4988 (5)0.2527 (4)0.1449 (3)0.0252 (8)
H31A0.38630.25470.16510.030*
H31B0.53130.33270.20230.030*
C320.6175 (5)0.1375 (4)0.1479 (4)0.0294 (9)
H32A0.72850.13590.12760.044*
H32B0.61770.14310.22590.044*
H32C0.58330.05880.09220.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt10.01206 (7)0.01043 (7)0.01114 (7)0.00036 (5)0.00234 (5)0.00484 (5)
Cl130.0219 (4)0.0151 (4)0.0148 (4)0.0047 (3)0.0009 (3)0.0023 (3)
O120.0083 (11)0.0158 (12)0.0217 (13)0.0014 (9)0.0011 (9)0.0082 (10)
O230.0211 (12)0.0163 (12)0.0153 (12)0.0041 (10)0.0066 (10)0.0094 (10)
O250.0152 (11)0.0143 (11)0.0150 (12)0.0034 (9)0.0024 (9)0.0097 (10)
O280.0191 (13)0.0301 (15)0.0315 (15)0.0090 (11)0.0115 (11)0.0217 (13)
O290.0192 (12)0.0137 (11)0.0117 (12)0.0025 (9)0.0004 (9)0.0074 (9)
N20.0153 (13)0.0102 (13)0.0099 (13)0.0015 (11)0.0012 (11)0.0068 (11)
C30.0163 (16)0.0157 (16)0.0138 (17)0.0052 (13)0.0020 (13)0.0078 (14)
C40.0112 (15)0.0200 (17)0.0183 (18)0.0039 (13)0.0015 (13)0.0113 (14)
C50.0122 (15)0.0149 (16)0.0144 (17)0.0028 (13)0.0034 (13)0.0090 (13)
C60.0155 (16)0.0113 (15)0.0121 (16)0.0004 (12)0.0016 (12)0.0082 (13)
C70.0202 (17)0.0131 (16)0.0108 (16)0.0003 (13)0.0024 (13)0.0054 (13)
C80.0253 (18)0.0150 (16)0.0125 (17)0.0065 (14)0.0029 (14)0.0048 (14)
C90.0168 (16)0.0188 (17)0.0161 (17)0.0062 (14)0.0031 (13)0.0085 (14)
C100.0144 (15)0.0127 (15)0.0120 (16)0.0006 (12)0.0002 (12)0.0078 (13)
C110.0139 (15)0.0120 (15)0.0108 (16)0.0022 (12)0.0011 (12)0.0081 (13)
C140.0139 (16)0.0171 (17)0.0195 (18)0.0022 (13)0.0071 (13)0.0095 (14)
C150.0115 (15)0.0162 (16)0.0143 (17)0.0014 (13)0.0057 (13)0.0063 (14)
C160.0114 (15)0.0185 (17)0.0169 (17)0.0014 (13)0.0015 (13)0.0085 (14)
C170.0099 (15)0.0116 (15)0.0199 (18)0.0019 (12)0.0000 (13)0.0076 (14)
C180.0147 (16)0.0158 (16)0.0157 (17)0.0031 (13)0.0003 (13)0.0094 (14)
C190.0117 (15)0.0114 (15)0.0173 (17)0.0024 (12)0.0013 (13)0.0067 (13)
C200.0102 (14)0.0095 (15)0.0152 (17)0.0028 (12)0.0030 (12)0.0056 (13)
C210.0143 (15)0.0151 (16)0.0126 (16)0.0032 (13)0.0010 (13)0.0063 (13)
C220.0125 (15)0.0109 (15)0.0167 (17)0.0007 (12)0.0022 (13)0.0037 (13)
C240.035 (2)0.030 (2)0.021 (2)0.0109 (18)0.0132 (17)0.0170 (17)
C260.0141 (16)0.0143 (16)0.0141 (17)0.0002 (13)0.0007 (13)0.0065 (14)
C270.0122 (15)0.0121 (15)0.0163 (17)0.0036 (13)0.0020 (13)0.0065 (13)
C300.0223 (18)0.0186 (18)0.027 (2)0.0013 (15)0.0014 (15)0.0112 (16)
C310.0216 (19)0.029 (2)0.030 (2)0.0067 (16)0.0041 (16)0.0184 (18)
C320.028 (2)0.030 (2)0.037 (2)0.0081 (17)0.0065 (18)0.0201 (19)
Geometric parameters (Å, º) top
Pt1—Cl132.2935 (8)C14—H14B0.9296
Pt1—O122.003 (2)C14—C151.389 (5)
Pt1—N22.042 (3)C15—H150.9789
Pt1—C142.136 (3)C15—C161.495 (5)
Pt1—C152.174 (3)C16—H16A0.9900
O12—C101.353 (4)C16—H16B0.9900
O23—C191.370 (4)C16—C171.519 (4)
O23—C241.423 (4)C17—C181.398 (5)
O25—C201.376 (4)C17—C221.380 (5)
O25—C261.413 (4)C18—H180.9500
O28—C271.198 (4)C18—C191.388 (5)
O29—C271.334 (4)C19—C201.405 (5)
O29—C301.461 (4)C20—C211.383 (4)
N2—C31.323 (4)C21—H210.9500
N2—C111.376 (4)C21—C221.397 (5)
C3—H30.9500C22—H220.9500
C3—C41.406 (5)C24—H24A0.9800
C4—H40.9500C24—H24B0.9800
C4—C51.369 (5)C24—H24C0.9800
C5—H50.9500C26—H26A0.9900
C5—C61.421 (5)C26—H26B0.9900
C6—C71.404 (5)C26—C271.510 (4)
C6—C111.413 (4)C30—H30A0.9900
C7—H70.9500C30—H30B0.9900
C7—C81.376 (5)C30—C311.511 (5)
C8—H80.9500C31—H31A0.9900
C8—C91.413 (5)C31—H31B0.9900
C9—H90.9500C31—C321.508 (5)
C9—C101.378 (5)C32—H32A0.9800
C10—C111.423 (4)C32—H32B0.9800
C14—H14A0.9291C32—H32C0.9800
O12—Pt1—Cl13176.98 (7)C15—C16—H16B108.6
O12—Pt1—N282.92 (10)C15—C16—C17114.8 (3)
O12—Pt1—C1490.86 (12)H16A—C16—H16B107.5
O12—Pt1—C1592.59 (11)C17—C16—H16A108.6
N2—Pt1—Cl1394.62 (8)C17—C16—H16B108.6
N2—Pt1—C14166.29 (12)C18—C17—C16120.0 (3)
N2—Pt1—C15154.39 (11)C22—C17—C16121.1 (3)
C14—Pt1—Cl1391.17 (10)C22—C17—C18118.9 (3)
C14—Pt1—C1537.59 (13)C17—C18—H18119.8
C15—Pt1—Cl1390.38 (9)C19—C18—C17120.5 (3)
C10—O12—Pt1111.51 (19)C19—C18—H18119.8
C19—O23—C24118.0 (3)O23—C19—C18124.8 (3)
C20—O25—C26116.5 (2)O23—C19—C20115.3 (3)
C27—O29—C30114.8 (3)C18—C19—C20119.9 (3)
C3—N2—Pt1129.5 (2)O25—C20—C19115.4 (3)
C3—N2—C11119.8 (3)O25—C20—C21124.8 (3)
C11—N2—Pt1110.6 (2)C21—C20—C19119.8 (3)
N2—C3—H3119.2C20—C21—H21120.2
N2—C3—C4121.5 (3)C20—C21—C22119.5 (3)
C4—C3—H3119.2C22—C21—H21120.2
C3—C4—H4120.0C17—C22—C21121.4 (3)
C5—C4—C3120.0 (3)C17—C22—H22119.3
C5—C4—H4120.0C21—C22—H22119.3
C4—C5—H5120.1O23—C24—H24A109.5
C4—C5—C6119.9 (3)O23—C24—H24B109.5
C6—C5—H5120.1O23—C24—H24C109.5
C7—C6—C5124.3 (3)H24A—C24—H24B109.5
C7—C6—C11118.8 (3)H24A—C24—H24C109.5
C11—C6—C5116.9 (3)H24B—C24—H24C109.5
C6—C7—H7120.5O25—C26—H26A110.1
C8—C7—C6119.1 (3)O25—C26—H26B110.1
C8—C7—H7120.5O25—C26—C27108.0 (3)
C7—C8—H8118.9H26A—C26—H26B108.4
C7—C8—C9122.2 (3)C27—C26—H26A110.1
C9—C8—H8118.9C27—C26—H26B110.1
C8—C9—H9119.8O28—C27—O29125.1 (3)
C10—C9—C8120.3 (3)O28—C27—C26125.3 (3)
C10—C9—H9119.8O29—C27—C26109.6 (3)
O12—C10—C9123.7 (3)O29—C30—H30A110.1
O12—C10—C11118.5 (3)O29—C30—H30B110.1
C9—C10—C11117.7 (3)O29—C30—C31108.1 (3)
N2—C11—C6121.8 (3)H30A—C30—H30B108.4
N2—C11—C10116.2 (3)C31—C30—H30A110.1
C6—C11—C10121.9 (3)C31—C30—H30B110.1
Pt1—C14—H14A112.7C30—C31—H31A109.8
Pt1—C14—H14B84.8C30—C31—H31B109.8
H14A—C14—H14B120.0H31A—C31—H31B108.2
C15—C14—Pt172.67 (19)C32—C31—C30109.5 (3)
C15—C14—H14A120.4C32—C31—H31A109.8
C15—C14—H14B119.7C32—C31—H31B109.8
Pt1—C15—H15114.1C31—C32—H32A109.5
C14—C15—Pt169.75 (19)C31—C32—H32B109.5
C14—C15—H15114.2C31—C32—H32C109.5
C14—C15—C16122.6 (3)H32A—C32—H32B109.5
C16—C15—Pt1114.4 (2)H32A—C32—H32C109.5
C16—C15—H15114.2H32B—C32—H32C109.5
C15—C16—H16A108.6
Pt1—O12—C10—C9175.2 (3)C8—C9—C10—O12177.9 (3)
Pt1—O12—C10—C113.0 (3)C8—C9—C10—C110.3 (5)
Pt1—N2—C3—C4175.9 (2)C9—C10—C11—N2178.9 (3)
Pt1—N2—C11—C6175.2 (2)C9—C10—C11—C60.1 (5)
Pt1—N2—C11—C103.8 (3)C11—N2—C3—C40.4 (5)
Pt1—C14—C15—C16106.6 (3)C11—C6—C7—C80.1 (5)
Pt1—C15—C16—C1775.3 (3)C14—C15—C16—C17156.0 (3)
O12—C10—C11—N20.6 (4)C15—C16—C17—C1888.9 (4)
O12—C10—C11—C6178.4 (3)C15—C16—C17—C2291.0 (4)
O23—C19—C20—O250.3 (4)C16—C17—C18—C19179.9 (3)
O23—C19—C20—C21179.9 (3)C16—C17—C22—C21178.8 (3)
O25—C20—C21—C22179.7 (3)C17—C18—C19—O23179.8 (3)
O25—C26—C27—O281.3 (5)C17—C18—C19—C200.8 (5)
O25—C26—C27—O29179.5 (3)C18—C17—C22—C211.3 (5)
O29—C30—C31—C32176.7 (3)C18—C19—C20—O25178.7 (3)
N2—C3—C4—C50.5 (5)C18—C19—C20—C210.8 (5)
C3—N2—C11—C61.7 (5)C19—C20—C21—C220.2 (5)
C3—N2—C11—C10179.3 (3)C20—O25—C26—C27179.0 (3)
C3—C4—C5—C60.1 (5)C20—C21—C22—C171.3 (5)
C4—C5—C6—C7179.7 (3)C22—C17—C18—C190.3 (5)
C4—C5—C6—C111.1 (5)C24—O23—C19—C180.1 (5)
C5—C6—C7—C8179.1 (3)C24—O23—C19—C20178.9 (3)
C5—C6—C11—N22.0 (5)C26—O25—C20—C19168.6 (3)
C5—C6—C11—C10179.0 (3)C26—O25—C20—C2110.9 (4)
C6—C7—C8—C90.3 (5)C27—O29—C30—C31166.0 (3)
C7—C6—C11—N2178.7 (3)C30—O29—C27—O282.8 (5)
C7—C6—C11—C100.3 (5)C30—O29—C27—C26178.0 (3)
C7—C8—C9—C100.5 (5)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of ring C6–C11, Cg2 is the centroid of ring N2/C3–C6/C11 and Cg3 is the centroid of ring C17–C22.
D—H···AD—HH···AD···AD—H···A
C16—H16B···O120.992.453.070 (4)120
C18—H18···O120.952.573.352 (5)140
C4—H4···O12i0.952.573.488 (4)163
C14—H14A···Cg2ii0.932.943.581 (4)127
C14—H14B···Cg1ii0.932.883.493 (4)125
C24—H24C···Cg10.982.913.513 (5)121
C32—H32A···Cg3iii0.982.843.655 (5)141
Symmetry codes: (i) x+1, y, z; (ii) x, y+2, z+1; (iii) x+1, y+1, z.
{η2-4-Allyl-2-methoxy-1-[(propan-2-yloxy)carbonylmethoxy]benzene}chlorido(quinolin-8-olato-κ2N,O)platinum(II) (chi9) top
Crystal data top
[Pt(C9H6NO)Cl(C15H20O4)]Z = 2
Mr = 639.00F(000) = 624
Triclinic, P1Dx = 1.830 Mg m3
a = 9.7858 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.0447 (2) ÅCell parameters from 30804 reflections
c = 11.8117 (3) Åθ = 3.3–29.2°
α = 85.059 (2)°µ = 6.20 mm1
β = 73.685 (3)°T = 200 K
γ = 71.139 (2)°Block, yellow
V = 1159.41 (6) Å30.3 × 0.25 × 0.15 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Eos detector
4738 independent reflections
Radiation source: SuperNova (Mo) X-ray Source4534 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.037
Detector resolution: 15.9631 pixels mm-1θmax = 26.4°, θmin = 2.7°
ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1313
Tmin = 0.369, Tmax = 1.000l = 1414
47800 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.017H-atom parameters constrained
wR(F2) = 0.041 w = 1/[σ2(Fo2) + (0.0139P)2 + 1.3246P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
4738 reflectionsΔρmax = 1.46 e Å3
292 parametersΔρmin = 1.01 e Å3
0 restraints
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
C30.1859 (3)0.5736 (3)0.8919 (3)0.0312 (6)
H30.1360260.5512460.9525790.037*
C40.1698 (3)0.6780 (3)0.8191 (3)0.0371 (7)
H40.1098060.7256130.8314370.044*
C50.2395 (3)0.7118 (3)0.7307 (3)0.0325 (6)
H50.2287890.7829960.6818750.039*
C60.3279 (3)0.6399 (3)0.7125 (2)0.0291 (6)
C70.4021 (4)0.6640 (3)0.6226 (3)0.0375 (7)
H70.3929720.7308190.5675520.045*
C80.4877 (4)0.5894 (3)0.6156 (3)0.0428 (8)
H80.5387020.6069630.5556030.051*
C90.5029 (4)0.4884 (3)0.6935 (3)0.0391 (7)
H90.5634510.4392840.6856320.047*
C100.4298 (3)0.4602 (3)0.7819 (2)0.0283 (6)
C110.3416 (3)0.5375 (2)0.7905 (2)0.0241 (5)
C140.3857 (4)0.2014 (3)1.0626 (3)0.0399 (7)
H14A0.3783150.1903731.1449810.048*
H14B0.4823990.1985551.0541090.048*
C150.2573 (4)0.1376 (3)0.9756 (3)0.0346 (7)
H150.1688090.0901471.0059240.042*
C160.2630 (3)0.0802 (3)0.8671 (3)0.0365 (7)
H16A0.3517130.1348640.8420300.044*
H16B0.2760760.0050140.8869360.044*
C170.1239 (3)0.0657 (3)0.7646 (3)0.0311 (6)
C180.1177 (3)0.1623 (3)0.6802 (3)0.0325 (6)
H180.2012210.2377080.6870360.039*
C190.0092 (3)0.1488 (3)0.5867 (2)0.0300 (6)
C200.1327 (3)0.0372 (3)0.5753 (2)0.0289 (6)
C210.1276 (3)0.0571 (3)0.6586 (3)0.0342 (6)
H210.2109960.1325990.6520780.041*
C220.0004 (4)0.0419 (3)0.7529 (3)0.0354 (7)
H220.0022760.1073840.8105180.042*
C240.0978 (4)0.3521 (3)0.5056 (3)0.0555 (10)
H24A0.0731600.4052870.4369140.083*
H24B0.1179730.3995430.5779580.083*
H24C0.1867980.3298170.5051510.083*
C260.3687 (3)0.0846 (3)0.4582 (3)0.0316 (6)
H26A0.3296140.1506760.4398420.038*
H26B0.4047770.1114600.5295490.038*
C270.4958 (3)0.0715 (3)0.3562 (3)0.0294 (6)
C300.7357 (3)0.1960 (3)0.2374 (3)0.0379 (7)
H300.7721780.1241780.2484670.046*
C310.7087 (4)0.1866 (4)0.1172 (3)0.0512 (9)
H31A0.8039870.1987750.0565070.077*
H31B0.6390970.1020570.1080530.077*
H31C0.6655970.2528560.1086400.077*
C320.8458 (4)0.3219 (3)0.2587 (4)0.0555 (10)
H32A0.8154620.3924740.2400740.083*
H32B0.8472820.3270290.3415670.083*
H32C0.9461360.3277890.2081080.083*
Cl130.14543 (9)0.33203 (8)1.08003 (7)0.04446 (19)
N20.2692 (2)0.5055 (2)0.87781 (19)0.0254 (5)
O120.4363 (2)0.36373 (18)0.85739 (18)0.0314 (4)
O230.0252 (2)0.23816 (19)0.50069 (18)0.0411 (5)
O250.2535 (2)0.03400 (18)0.47921 (18)0.0354 (5)
O280.5090 (3)0.0266 (2)0.3106 (2)0.0453 (6)
O290.5949 (2)0.18764 (18)0.32815 (18)0.0323 (4)
Pt10.29907 (2)0.34304 (2)0.96161 (2)0.02646 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.0306 (15)0.0285 (14)0.0353 (16)0.0075 (12)0.0114 (12)0.0024 (12)
C40.0318 (16)0.0302 (15)0.0499 (19)0.0122 (13)0.0086 (14)0.0014 (13)
C50.0315 (15)0.0225 (14)0.0339 (16)0.0042 (12)0.0009 (12)0.0019 (11)
C60.0298 (14)0.0228 (13)0.0235 (13)0.0014 (11)0.0005 (11)0.0017 (10)
C70.0478 (19)0.0263 (15)0.0299 (15)0.0003 (13)0.0120 (14)0.0033 (12)
C80.050 (2)0.0377 (17)0.0386 (18)0.0019 (15)0.0258 (16)0.0024 (14)
C90.0384 (17)0.0368 (17)0.0458 (19)0.0071 (14)0.0209 (15)0.0047 (14)
C100.0250 (14)0.0243 (14)0.0309 (15)0.0011 (11)0.0071 (11)0.0020 (11)
C110.0217 (13)0.0198 (12)0.0241 (13)0.0002 (10)0.0024 (10)0.0034 (10)
C140.0438 (18)0.0311 (16)0.0331 (16)0.0125 (14)0.0061 (14)0.0092 (13)
C150.0405 (17)0.0235 (14)0.0291 (15)0.0068 (12)0.0012 (13)0.0080 (11)
C160.0381 (17)0.0280 (15)0.0395 (17)0.0132 (13)0.0015 (14)0.0031 (12)
C170.0365 (16)0.0249 (14)0.0298 (15)0.0122 (12)0.0025 (12)0.0010 (11)
C180.0339 (16)0.0245 (14)0.0315 (15)0.0041 (12)0.0025 (12)0.0013 (11)
C190.0344 (15)0.0239 (14)0.0250 (14)0.0040 (12)0.0040 (12)0.0008 (11)
C200.0315 (15)0.0267 (14)0.0236 (14)0.0054 (12)0.0038 (11)0.0014 (11)
C210.0393 (17)0.0234 (14)0.0335 (16)0.0037 (12)0.0072 (13)0.0013 (12)
C220.0471 (18)0.0239 (14)0.0315 (15)0.0127 (13)0.0044 (13)0.0046 (12)
C240.047 (2)0.0341 (18)0.055 (2)0.0089 (15)0.0041 (17)0.0179 (16)
C260.0308 (15)0.0239 (14)0.0321 (15)0.0009 (12)0.0045 (12)0.0012 (11)
C270.0280 (14)0.0255 (14)0.0327 (15)0.0040 (11)0.0090 (12)0.0045 (12)
C300.0269 (15)0.0352 (16)0.0465 (18)0.0092 (13)0.0004 (13)0.0089 (14)
C310.043 (2)0.063 (2)0.0398 (19)0.0156 (17)0.0024 (15)0.0077 (17)
C320.0304 (18)0.046 (2)0.079 (3)0.0011 (15)0.0075 (18)0.0070 (19)
Cl130.0453 (4)0.0485 (5)0.0394 (4)0.0074 (4)0.0220 (4)0.0084 (3)
N20.0240 (11)0.0230 (11)0.0254 (11)0.0037 (9)0.0051 (9)0.0001 (9)
O120.0292 (10)0.0289 (10)0.0366 (11)0.0113 (8)0.0084 (9)0.0047 (8)
O230.0392 (12)0.0298 (11)0.0312 (11)0.0048 (9)0.0052 (9)0.0103 (9)
O250.0327 (11)0.0249 (10)0.0319 (11)0.0027 (8)0.0027 (9)0.0035 (8)
O280.0419 (13)0.0243 (11)0.0556 (15)0.0047 (9)0.0018 (11)0.0018 (10)
O290.0286 (10)0.0247 (10)0.0363 (11)0.0037 (8)0.0018 (9)0.0033 (8)
Pt10.02589 (6)0.02385 (6)0.02392 (6)0.00394 (4)0.00313 (4)0.00299 (4)
Geometric parameters (Å, º) top
C3—H30.9500C18—C191.387 (4)
C3—C41.401 (4)C19—C201.404 (4)
C3—N21.323 (3)C19—O231.367 (3)
C4—H40.9500C20—C211.374 (4)
C4—C51.365 (4)C20—O251.383 (3)
C5—H50.9500C21—H210.9500
C5—C61.416 (4)C21—C221.397 (4)
C6—C71.410 (4)C22—H220.9500
C6—C111.413 (4)C24—H24A0.9800
C7—H70.9500C24—H24B0.9800
C7—C81.372 (5)C24—H24C0.9800
C8—H80.9500C24—O231.424 (4)
C8—C91.403 (5)C26—H26A0.9900
C9—H90.9500C26—H26B0.9900
C9—C101.385 (4)C26—C271.505 (4)
C10—C111.423 (4)C26—O251.411 (3)
C10—O121.335 (3)C27—O281.196 (3)
C11—N21.370 (3)C27—O291.336 (3)
C14—H14A0.9900C30—H301.0000
C14—H14B0.9900C30—C311.505 (5)
C14—C151.400 (4)C30—C321.510 (5)
C14—Pt12.134 (3)C30—O291.470 (3)
C15—H151.0000C31—H31A0.9800
C15—C161.501 (4)C31—H31B0.9800
C15—Pt12.172 (3)C31—H31C0.9800
C16—H16A0.9900C32—H32A0.9800
C16—H16B0.9900C32—H32B0.9800
C16—C171.520 (4)C32—H32C0.9800
C17—C181.400 (4)Cl13—Pt12.2947 (8)
C17—C221.378 (4)N2—Pt12.039 (2)
C18—H180.9500O12—Pt12.0135 (19)
C4—C3—H3119.3C20—C21—H21120.1
N2—C3—H3119.3C20—C21—C22119.9 (3)
N2—C3—C4121.5 (3)C22—C21—H21120.1
C3—C4—H4119.7C17—C22—C21121.6 (3)
C5—C4—C3120.5 (3)C17—C22—H22119.2
C5—C4—H4119.7C21—C22—H22119.2
C4—C5—H5120.3H24A—C24—H24B109.5
C4—C5—C6119.4 (3)H24A—C24—H24C109.5
C6—C5—H5120.3H24B—C24—H24C109.5
C7—C6—C5124.4 (3)O23—C24—H24A109.5
C7—C6—C11118.5 (3)O23—C24—H24B109.5
C11—C6—C5117.1 (3)O23—C24—H24C109.5
C6—C7—H7120.5H26A—C26—H26B108.3
C8—C7—C6119.0 (3)C27—C26—H26A109.8
C8—C7—H7120.5C27—C26—H26B109.8
C7—C8—H8118.7O25—C26—H26A109.8
C7—C8—C9122.7 (3)O25—C26—H26B109.8
C9—C8—H8118.7O25—C26—C27109.3 (2)
C8—C9—H9119.9O28—C27—C26125.9 (3)
C10—C9—C8120.2 (3)O28—C27—O29125.6 (3)
C10—C9—H9119.9O29—C27—C26108.4 (2)
C9—C10—C11117.6 (3)C31—C30—H30109.5
O12—C10—C9123.4 (3)C31—C30—C32113.5 (3)
O12—C10—C11118.9 (2)C32—C30—H30109.5
C6—C11—C10122.0 (2)O29—C30—H30109.5
N2—C11—C6122.0 (2)O29—C30—C31109.4 (3)
N2—C11—C10116.0 (2)O29—C30—C32105.4 (3)
H14A—C14—H14B113.3C30—C31—H31A109.5
C15—C14—H14A116.3C30—C31—H31B109.5
C15—C14—H14B116.3C30—C31—H31C109.5
C15—C14—Pt172.51 (16)H31A—C31—H31B109.5
Pt1—C14—H14A116.3H31A—C31—H31C109.5
Pt1—C14—H14B116.3H31B—C31—H31C109.5
C14—C15—H15114.5C30—C32—H32A109.5
C14—C15—C16123.1 (3)C30—C32—H32B109.5
C14—C15—Pt169.57 (16)C30—C32—H32C109.5
C16—C15—H15114.5H32A—C32—H32B109.5
C16—C15—Pt1112.57 (19)H32A—C32—H32C109.5
Pt1—C15—H15114.5H32B—C32—H32C109.5
C15—C16—H16A108.8C3—N2—C11119.5 (2)
C15—C16—H16B108.8C3—N2—Pt1129.50 (19)
C15—C16—C17113.6 (3)C11—N2—Pt1110.82 (17)
H16A—C16—H16B107.7C10—O12—Pt1111.41 (16)
C17—C16—H16A108.8C19—O23—C24118.1 (2)
C17—C16—H16B108.8C20—O25—C26115.3 (2)
C18—C17—C16120.7 (3)C27—O29—C30117.6 (2)
C22—C17—C16121.0 (3)C14—Pt1—C1537.92 (11)
C22—C17—C18118.3 (3)C14—Pt1—Cl1392.02 (10)
C17—C18—H18119.7C15—Pt1—Cl1390.47 (9)
C19—C18—C17120.6 (3)N2—Pt1—C14166.07 (11)
C19—C18—H18119.7N2—Pt1—C15153.86 (10)
C18—C19—C20120.2 (3)N2—Pt1—Cl1394.65 (7)
O23—C19—C18124.5 (3)O12—Pt1—C1490.51 (11)
O23—C19—C20115.3 (2)O12—Pt1—C1592.84 (10)
C21—C20—C19119.4 (3)O12—Pt1—Cl13176.69 (6)
C21—C20—O25125.2 (3)O12—Pt1—N282.43 (8)
O25—C20—C19115.4 (2)
C3—C4—C5—C60.4 (4)C17—C18—C19—C200.5 (4)
C4—C3—N2—C110.1 (4)C17—C18—C19—O23179.8 (3)
C4—C3—N2—Pt1174.8 (2)C18—C17—C22—C211.3 (4)
C4—C5—C6—C7178.5 (3)C18—C19—C20—C211.2 (4)
C4—C5—C6—C111.5 (4)C18—C19—C20—O25179.7 (3)
C5—C6—C7—C8178.4 (3)C18—C19—O23—C241.3 (5)
C5—C6—C11—C10178.8 (2)C19—C20—C21—C220.6 (4)
C5—C6—C11—N22.1 (4)C19—C20—O25—C26171.4 (2)
C6—C7—C8—C91.0 (5)C20—C19—O23—C24178.4 (3)
C6—C11—N2—C31.3 (4)C20—C21—C22—C170.7 (5)
C6—C11—N2—Pt1174.45 (19)C21—C20—O25—C2610.1 (4)
C7—C6—C11—C101.2 (4)C22—C17—C18—C190.7 (4)
C7—C6—C11—N2178.0 (2)C26—C27—O29—C30174.5 (2)
C7—C8—C9—C100.1 (5)C27—C26—O25—C20176.6 (2)
C8—C9—C10—C110.5 (4)C31—C30—O29—C2779.9 (3)
C8—C9—C10—O12178.4 (3)C32—C30—O29—C27157.7 (3)
C9—C10—C11—C60.1 (4)N2—C3—C4—C50.4 (5)
C9—C10—C11—N2179.1 (2)O12—C10—C11—C6179.1 (2)
C9—C10—O12—Pt1174.3 (2)O12—C10—C11—N20.1 (4)
C10—C11—N2—C3179.5 (2)O23—C19—C20—C21179.1 (3)
C10—C11—N2—Pt14.7 (3)O23—C19—C20—O250.5 (4)
C11—C6—C7—C81.6 (4)O25—C20—C21—C22179.0 (3)
C11—C10—O12—Pt14.7 (3)O25—C26—C27—O2810.2 (4)
C14—C15—C16—C17156.2 (3)O25—C26—C27—O29172.3 (2)
C15—C16—C17—C1892.4 (3)O28—C27—O29—C303.0 (4)
C15—C16—C17—C2286.9 (3)Pt1—C14—C15—C16104.3 (3)
C16—C17—C18—C19180.0 (3)Pt1—C15—C16—C1776.6 (3)
C16—C17—C22—C21179.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of ring N2/C3–C6/C11, Cg2 is the centroid of ring C6–C11 and Cg3 is the centroid of ring C17–C22.
D—H···AD—HH···AD···AD—H···A
C5—H5···O23i0.952.463.073 (4)122
C16—H16A···O120.992.403.051 (4)123
C14—H14B···Cg1ii0.992.943.454 (4)114
C24—H24B···Cg20.982.933.564 (4)124
C30—H30···Cg3iii1.002.963.827 (4)145
Symmetry codes: (i) x, y+1, z+1; (ii) x1, y, z+1; (iii) x+1, y, z+1.
[η2-4-Allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-2-carboxylato-κ2N,O)platinum(II) (chi33) top
Crystal data top
[Pt(C10H6O2)Cl(C15H20O4)]F(000) = 1304
Mr = 667.01Dx = 1.879 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.6457 (13) ÅCell parameters from 6260 reflections
b = 9.7291 (4) Åθ = 3.4–28.0°
c = 16.6062 (8) ŵ = 6.11 mm1
β = 111.150 (8)°T = 100 K
V = 2357.5 (3) Å3Needle, yellow
Z = 40.3 × 0.15 × 0.10 mm
Data collection top
Agilent SuperNova Dual Source
diffractometer with an Eos detector
4030 independent reflections
Radiation source: SuperNova (Mo) X-ray Source3348 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.066
Detector resolution: 15.9631 pixels mm-1θmax = 24.7°, θmin = 2.8°
ω scansh = 1818
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1111
Tmin = 0.522, Tmax = 1.000l = 1919
21714 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0209P)2 + 13.4203P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
4030 reflectionsΔρmax = 2.22 e Å3
316 parametersΔρmin = 1.13 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*/UeqOcc. (<1)
Pt1A0.69372 (3)0.90310 (4)0.69364 (2)0.02742 (15)0.9298 (13)
Pt1B0.6573 (5)0.9379 (6)0.7023 (3)0.02742 (15)0.0702 (13)
Cl2A0.74945 (19)1.1196 (2)0.69048 (14)0.0519 (7)0.9298 (13)
Cl2B0.710 (3)1.143 (4)0.711 (2)0.0519 (7)0.0702 (13)
N30.6096 (4)0.8677 (6)0.5632 (3)0.0261 (13)
C40.5626 (5)0.7531 (7)0.5569 (4)0.0281 (16)
C50.5000 (5)0.7022 (8)0.4798 (4)0.0380 (18)
H50.4666600.6203520.4793420.046*
C60.4873 (6)0.7711 (9)0.4056 (5)0.045 (2)
H60.4444340.7383690.3524630.054*
C70.5374 (5)0.8902 (8)0.4075 (5)0.0399 (19)
C80.5288 (6)0.9618 (9)0.3313 (5)0.049 (2)
H80.4860900.9302610.2777790.058*
C90.5800 (6)1.0743 (10)0.3325 (5)0.052 (2)
H90.5736861.1210770.2804970.063*
C100.6428 (6)1.1212 (8)0.4123 (5)0.048 (2)
H100.6786261.2005570.4136620.058*
C110.6532 (6)1.0544 (8)0.4881 (5)0.0403 (19)
H110.6963391.0872520.5410040.048*
C120.6004 (5)0.9381 (7)0.4874 (4)0.0302 (16)
C130.5797 (5)0.6706 (8)0.6392 (4)0.0326 (17)
O140.6441 (4)0.7167 (5)0.7062 (3)0.0403 (13)
O150.5356 (4)0.5679 (5)0.6383 (3)0.0402 (13)
C160.8065 (5)0.8737 (8)0.8114 (4)0.0360 (18)
H16A0.8209570.7792830.8234590.043*
H16B0.8395520.9272130.7846160.043*
C170.7365 (5)0.9339 (8)0.8331 (4)0.041 (2)
H170.7475811.0319300.8521650.049*0.9298 (13)
H17A0.7527051.0279240.8583480.049*0.0702 (13)
C180.6843 (6)0.8543 (9)0.8744 (5)0.047 (2)
H18A0.6883240.7550370.8630720.057*
H18B0.6189400.8816930.8507530.057*
C190.7245 (5)0.8821 (9)0.9717 (4)0.041 (2)
C200.7935 (5)0.7966 (8)1.0248 (4)0.0373 (18)
H200.8147970.7216621.0005300.045*
C210.8313 (5)0.8211 (8)1.1136 (4)0.0323 (17)
C220.7985 (5)0.9311 (7)1.1495 (4)0.0304 (17)
C230.7315 (5)1.0157 (8)1.0962 (4)0.0358 (17)
H230.7105721.0920861.1195980.043*
C240.6942 (5)0.9891 (8)1.0073 (4)0.0396 (19)
H240.6468991.0467000.9711740.047*
O250.8981 (3)0.7447 (5)1.1711 (3)0.0414 (13)
C260.9278 (6)0.6241 (9)1.1385 (5)0.054 (2)
H26A0.9497830.6503551.0923960.081*
H26B0.8763670.5600411.1156660.081*
H26C0.9775600.5797451.1853850.081*
O270.8385 (3)0.9431 (5)1.2376 (3)0.0336 (12)
C280.8073 (5)1.0523 (7)1.2750 (4)0.0345 (18)
H28A0.7399191.0468701.2584440.041*
H28B0.8225181.1411731.2544170.041*
C290.8532 (5)1.0422 (8)1.3717 (4)0.0305 (16)
O300.8787 (4)0.9389 (5)1.4110 (3)0.0367 (12)
O310.8578 (3)1.1679 (5)1.4060 (3)0.0366 (12)
C320.8972 (5)1.1747 (8)1.4997 (4)0.0414 (19)
H32A0.9529581.1169831.5212700.050*
H32B0.8526201.1393111.5244700.050*
C330.9208 (6)1.3209 (8)1.5269 (5)0.050 (2)
H33A0.8663201.3801391.5009890.060*
H33B0.9696421.3536751.5067870.060*
C340.9536 (7)1.3289 (11)1.6247 (5)0.066 (3)
H34A0.9721621.4233551.6433410.099*
H34B1.0059731.2671051.6498910.099*
H34C0.9038061.3013051.6439040.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt1A0.0359 (3)0.0302 (2)0.01614 (15)0.00021 (17)0.00946 (13)0.00123 (13)
Pt1B0.0359 (3)0.0302 (2)0.01614 (15)0.00021 (17)0.00946 (13)0.00123 (13)
Cl2A0.0799 (19)0.0368 (13)0.0309 (12)0.0187 (12)0.0103 (11)0.0034 (9)
Cl2B0.0799 (19)0.0368 (13)0.0309 (12)0.0187 (12)0.0103 (11)0.0034 (9)
N30.030 (3)0.034 (4)0.017 (3)0.006 (3)0.012 (2)0.001 (2)
C40.031 (4)0.036 (4)0.020 (3)0.004 (3)0.011 (3)0.001 (3)
C50.039 (4)0.053 (5)0.021 (4)0.007 (4)0.010 (3)0.009 (3)
C60.057 (5)0.055 (6)0.022 (4)0.008 (4)0.012 (4)0.004 (4)
C70.051 (5)0.052 (5)0.025 (4)0.018 (4)0.023 (4)0.002 (3)
C80.072 (6)0.058 (6)0.020 (4)0.015 (5)0.022 (4)0.009 (4)
C90.072 (6)0.067 (6)0.028 (4)0.031 (5)0.030 (4)0.016 (4)
C100.061 (6)0.042 (5)0.053 (5)0.010 (4)0.033 (5)0.019 (4)
C110.054 (5)0.043 (5)0.028 (4)0.010 (4)0.020 (4)0.007 (3)
C120.036 (4)0.038 (4)0.021 (4)0.010 (3)0.015 (3)0.006 (3)
C130.037 (4)0.041 (5)0.022 (4)0.000 (4)0.013 (3)0.002 (3)
O140.064 (4)0.041 (3)0.013 (2)0.013 (3)0.010 (2)0.004 (2)
O150.051 (3)0.048 (3)0.025 (3)0.022 (3)0.018 (2)0.005 (2)
C160.043 (4)0.041 (5)0.022 (4)0.004 (4)0.009 (3)0.004 (3)
C170.056 (5)0.049 (5)0.010 (3)0.003 (4)0.003 (3)0.002 (3)
C180.050 (5)0.062 (6)0.030 (4)0.013 (4)0.016 (4)0.008 (4)
C190.047 (5)0.059 (6)0.019 (4)0.013 (4)0.015 (4)0.002 (4)
C200.048 (5)0.042 (5)0.031 (4)0.013 (4)0.026 (4)0.013 (3)
C210.034 (4)0.038 (4)0.029 (4)0.005 (3)0.015 (3)0.003 (3)
C220.037 (4)0.037 (4)0.019 (3)0.012 (3)0.013 (3)0.000 (3)
C230.040 (4)0.042 (5)0.026 (4)0.001 (4)0.013 (3)0.003 (3)
C240.041 (5)0.055 (5)0.020 (4)0.005 (4)0.009 (3)0.001 (3)
O250.049 (3)0.048 (3)0.030 (3)0.005 (3)0.017 (3)0.009 (2)
C260.066 (6)0.054 (6)0.046 (5)0.011 (5)0.027 (5)0.009 (4)
O270.041 (3)0.036 (3)0.022 (2)0.001 (2)0.009 (2)0.005 (2)
C280.052 (5)0.033 (4)0.016 (3)0.000 (3)0.009 (3)0.001 (3)
C290.035 (4)0.030 (4)0.031 (4)0.002 (3)0.017 (3)0.003 (3)
O300.053 (3)0.032 (3)0.023 (3)0.000 (2)0.011 (2)0.001 (2)
O310.056 (3)0.030 (3)0.020 (2)0.003 (2)0.010 (2)0.003 (2)
C320.048 (5)0.053 (5)0.022 (4)0.003 (4)0.012 (4)0.004 (3)
C330.067 (6)0.045 (5)0.032 (4)0.012 (4)0.008 (4)0.018 (4)
C340.067 (7)0.085 (7)0.039 (5)0.011 (5)0.011 (5)0.023 (5)
Geometric parameters (Å, º) top
PT1Aa—Cl2A2.287 (2)C17—C181.464 (11)
PT1Bb—Cl2B2.14 (3)C18—H18A0.9900
PT1Aa—N32.118 (5)C18—H18B0.9900
PT1Bb—N32.262 (7)C18—C191.533 (10)
PT1Aa—O142.013 (5)C19—C201.396 (11)
PT1Bb—O142.166 (7)C19—C241.363 (11)
PT1Bb—C162.464 (9)C20—H200.9500
PT1Aa—C162.128 (7)C20—C211.397 (9)
PT1Aa—C172.186 (6)C21—C221.409 (10)
PT1Bb—C172.077 (8)C21—O251.355 (8)
N3—C41.320 (9)C22—C231.374 (10)
N3—C121.393 (8)C22—O271.373 (7)
C4—C51.392 (9)C23—H230.9500
C4—C131.522 (9)C23—C241.402 (9)
C5—H50.9500C24—H240.9500
C5—C61.353 (10)O25—C261.437 (9)
C6—H60.9500C26—H26A0.9800
C6—C71.393 (11)C26—H26B0.9800
C7—C81.408 (10)C26—H26C0.9800
C7—C121.416 (10)O27—C281.405 (8)
C8—H80.9500C28—H28A0.9900
C8—C91.352 (12)C28—H28B0.9900
C9—H90.9500C28—C291.508 (9)
C9—C101.411 (12)C29—O301.186 (8)
C10—H100.9500C29—O311.340 (8)
C10—C111.372 (10)O31—C321.453 (8)
C11—H110.9500C32—H32A0.9900
C11—C121.399 (10)C32—H32B0.9900
C13—O141.283 (8)C32—C331.498 (11)
C13—O151.212 (8)C33—H33A0.9900
C16—H16A0.9500C33—H33B0.9900
C16—H16B0.9500C33—C341.518 (10)
C16—C171.399 (10)C34—H34A0.9800
C17—H171.0000C34—H34B0.9800
C17—H17A1.0000C34—H34C0.9800
CL2Bb—PT1Bb—N3108.9 (9)C17—PT1Bb—N3156.2 (5)
CL2Bb—PT1Bb—O14163.9 (12)C17—PT1Bb—O1488.7 (3)
CL2Bb—PT1Bb—C1687.0 (10)C17—PT1Bb—C1634.6 (3)
PT1Aa—C16—H16A112.3C18—C17—Pt1A114.5 (5)
PT1Aa—C16—H16B84.7C18—C17—Pt1B106.1 (5)
H16Aa—C16—H16B120.0C18—C17—H17114.7
PT1Aa—C17—H17114.7C18—C17—H17A112.8
PT1Bb—C17—H17A112.8C17—C18—H18A110.0
N3—PT1Aa—Cl2A103.13 (16)C17—C18—H18B110.0
N3—PT1Bb—C16123.4 (4)C17—C18—C19108.3 (6)
N3—PT1Aa—C16157.1 (2)H18A—C18—H18B108.4
N3—PT1Aa—C17161.0 (3)C19—C18—H18A110.0
C4—N3—Pt1A109.9 (4)C19—C18—H18B110.0
C4—N3—Pt1B107.7 (4)C20—C19—C18119.4 (7)
C4—N3—C12118.1 (6)C24—C19—C18121.2 (7)
C12—N3—Pt1A131.9 (5)C24—C19—C20119.5 (7)
C12—N3—Pt1B131.5 (5)C19—C20—H20120.0
N3—C4—C5124.0 (6)C19—C20—C21120.1 (7)
N3—C4—C13117.5 (6)C21—C20—H20120.0
C5—C4—C13118.4 (7)C20—C21—C22119.7 (7)
C4—C5—H5120.5O25—C21—C20125.1 (7)
C6—C5—C4119.0 (8)O25—C21—C22115.2 (6)
C6—C5—H5120.5C23—C22—C21119.5 (6)
C5—C6—H6120.2O27—C22—C21114.8 (6)
C5—C6—C7119.6 (7)O27—C22—C23125.7 (7)
C7—C6—H6120.2C22—C23—H23120.1
C6—C7—C8121.4 (8)C22—C23—C24119.9 (7)
C6—C7—C12119.4 (7)C24—C23—H23120.1
C8—C7—C12119.2 (8)C19—C24—C23121.3 (7)
C7—C8—H8119.2C19—C24—H24119.3
C9—C8—C7121.5 (8)C23—C24—H24119.3
C9—C8—H8119.2C21—O25—C26117.1 (6)
C8—C9—H9120.5O25—C26—H26A109.5
C8—C9—C10118.9 (7)O25—C26—H26B109.5
C10—C9—H9120.5O25—C26—H26C109.5
C9—C10—H10119.3H26A—C26—H26B109.5
C11—C10—C9121.3 (8)H26A—C26—H26C109.5
C11—C10—H10119.3H26B—C26—H26C109.5
C10—C11—H11119.9C22—O27—C28115.9 (5)
C10—C11—C12120.1 (8)O27—C28—H28A110.0
C12—C11—H11119.9O27—C28—H28B110.0
N3—C12—C7119.6 (7)O27—C28—C29108.3 (6)
N3—C12—C11121.5 (6)H28A—C28—H28B108.4
C11—C12—C7118.8 (6)C29—C28—H28A110.0
O14—C13—C4115.1 (6)C29—C28—H28B110.0
O15—C13—C4120.6 (6)O30—C29—C28125.3 (7)
O15—C13—O14124.3 (6)O30—C29—O31125.7 (6)
C13—O14—Pt1A115.8 (4)O31—C29—C28109.0 (6)
C13—O14—Pt1B112.0 (5)C29—O31—C32115.7 (6)
C17—C16—Pt1A73.4 (4)O31—C32—H32A109.8
O14—PT1Aa—Cl2A175.13 (14)O31—C32—H32B109.8
O14—PT1Aa—N380.8 (2)O31—C32—C33109.2 (6)
O14—PT1Bb—N374.4 (2)H32A—C32—H32B108.3
O14—PT1Aa—C1690.4 (2)C33—C32—H32A109.8
O14—PT1Bb—C1678.5 (3)C33—C32—H32B109.8
O14—PT1Aa—C1789.8 (3)C32—C33—H33A109.9
C16—PT1Aa—Cl2A87.0 (2)C32—C33—H33B109.9
C16—PT1Aa—C1737.8 (3)C32—C33—C34108.8 (7)
C17—C16—Pt1B57.4 (4)H33A—C33—H33B108.3
C17—C16—H16A120.0C34—C33—H33A109.9
C17—C16—H16B120.0C34—C33—H33B109.9
C16—C17—Pt1A68.8 (4)C33—C34—H34A109.5
C16—C17—Pt1B88.0 (5)C33—C34—H34B109.5
C16—C17—H17114.7C33—C34—H34C109.5
C16—C17—H17A112.8H34A—C34—H34B109.5
C16—C17—C18121.3 (7)H34A—C34—H34C109.5
C17—PT1Aa—Cl2A85.7 (2)H34B—C34—H34C109.5
C17—PT1Bb—Cl2B83.1 (9)
PT1Aa—N3—C4—C5179.0 (6)O15—C13—O14—PT1Bb150.9 (7)
PT1Bb—N3—C4—C5159.5 (6)O15—C13—O14—PT1Aa171.7 (6)
PT1Aa—N3—C4—C132.3 (7)PT1Aa—C16—C17—C18106.5 (7)
PT1Bb—N3—C4—C1321.8 (7)PT1Bb—C16—C17—C18107.7 (7)
PT1Bb—N3—C12—C7155.0 (6)PT1Aa—C17—C18—C19177.7 (5)
PT1Aa—N3—C12—C7180.0 (5)PT1Bb—C17—C18—C19163.8 (6)
PT1Bb—N3—C12—C1126.1 (10)C16—C17—C18—C1998.5 (8)
PT1Aa—N3—C12—C111.2 (10)C17—C18—C19—C2091.5 (9)
N3—C4—C5—C61.8 (11)C17—C18—C19—C2488.3 (9)
N3—C4—C13—O144.9 (9)C18—C19—C20—C21179.6 (6)
N3—C4—C13—O15176.6 (6)C18—C19—C24—C23179.3 (7)
C4—N3—C12—C73.8 (9)C19—C20—C21—C221.0 (10)
C4—N3—C12—C11175.0 (6)C19—C20—C21—O25179.7 (7)
C4—C5—C6—C70.6 (11)C20—C19—C24—C230.5 (11)
C4—C13—O14—PT1Bb30.8 (8)C20—C21—C22—C232.1 (10)
C4—C13—O14—PT1Aa10.0 (8)C20—C21—C22—O27178.1 (6)
C5—C4—C13—O14173.9 (6)C20—C21—O25—C264.3 (10)
C5—C4—C13—O154.6 (10)C21—C22—C23—C242.3 (11)
C5—C6—C7—C8177.5 (7)C21—C22—O27—C28179.7 (6)
C5—C6—C7—C120.6 (11)C22—C21—O25—C26174.5 (6)
C6—C7—C8—C9177.4 (8)C22—C23—C24—C191.6 (11)
C6—C7—C12—N31.7 (10)C22—O27—C28—C29175.6 (6)
C6—C7—C12—C11177.3 (7)C23—C22—O27—C280.1 (10)
C7—C8—C9—C100.5 (12)C24—C19—C20—C210.2 (11)
C8—C7—C12—N3179.8 (6)O25—C21—C22—C23179.1 (6)
C8—C7—C12—C110.9 (10)O25—C21—C22—O270.7 (9)
C8—C9—C10—C110.4 (12)O27—C22—C23—C24177.9 (6)
C9—C10—C11—C120.6 (12)O27—C28—C29—O3028.6 (10)
C10—C11—C12—N3179.7 (7)O27—C28—C29—O31153.3 (6)
C10—C11—C12—C70.8 (11)C28—C29—O31—C32177.5 (6)
C12—N3—C4—C54.0 (10)C29—O31—C32—C33164.9 (7)
C12—N3—C4—C13174.7 (6)O30—C29—O31—C320.5 (10)
C12—C7—C8—C90.7 (12)O31—C32—C33—C34174.8 (7)
C13—C4—C5—C6176.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···Cl2A0.952.343.211 (8)153
C11—H11···Cl2B0.952.813.59 (3)140
C16—H16A···O30i0.952.553.452 (9)159
C20—H20···O30i0.952.593.524 (9)167
C28—H28B···Cl2Aii0.992.643.473 (7)142
C32—H32A···O30iii0.992.523.459 (10)158
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x, y+5/2, z+1/2; (iii) x+2, y+2, z+3.
Cations and anions detected by ESI mass spectroscopy (m/z, %) for complexes (2)–(6) and several other platinum(II) complexes top
Complexes[M – Cl]+[M + H]+[M – H]-[M – AlkEug + Cl]-[2(M–Qui–HCl) + Cl]-
[PtCl2(PrEug)(Qui)] (2)----1022 (100)
[PtCl2(iPrEug)(Qui)] (3)----1022 (100)
[PtCl(Qui-O)(PrEug)] (4)603 (100)640 (50)637 (45)409 (40)-
[PtCl(Qui-O)(iPrEug)] (5)603 (100)640 (35)637 (100)409 (75)-
[PtCl(Qui-COO)(PrEug)] (6)631 (100)667 (25)666 (10)438 (25)-
[PtCl(Qui-O)(Eug)]a503 (100)540 (25)---
[PtCl(MeQui-O)(Eug)]b517 (100)553 (10)---
[PtCl(NO2Qui-O)(Eug)]b548 (100)584 (80)---
[PtCl(ClQui-O)(Eug)]b571 (100)607 (20)---
References: (a) Chi et al. (2017a); (b) Chi et al. (2017b).
Chemical shift (ppm), multiplicity and coupling constant JPt-H (Hz) of H8, H9, H10, H12 and H18 in free AlkEug and in (1)–(6)a top
CompoundH8aH8bH9H10transH10cisH12H18
Free PrEug3.32 d5.96 m5.06 dd5.01 dd
Free iPrEug3.32 d5.96 m5.08–5.00 ov
(1a)b2.98 dd3.49 dd5.05 m4.30 dd4.13 ov
2JPt-H 702JPt-H 70
(1b)c2.87 dd3.48 dd5.00 m4.27 dd4.10 dd
2JPt-H 702JPt-H 702JPt-H 70
(2)3.31 dd3.61 dd5.91 m4.83 dd4.72 dd9.03 d8.82 br
2JPt-H 702JPt-H 702JPt-H 70
(3)3.31 dd3.61 dd5.91 m4.83 dd4.72 dd9.02 d8.82 br
3JPt-H 502JPt-H 702JPt-H 702JPt-H 70
(4)d3.27 dd3.59 dd5.59 m4.76 d4.73 d9.07 d
3JPt-H 502JPt-H 702JPt-H 702JPt-H 703JPt-H 34
(5)3.27 dd3.60 dd5.61 m4.76 d4.74 d9.07 d
3JPt-H 502JPt-H 702JPt-H 702JPt-H 703JPt-H 34
(6)e3.22 br3.57 br5.90 m4.88–4.91 ov4.88–4.91 ov9.58 d
2JPt-H 70
Notes/references: (a) acetone-d6; (b) Chi et al. (2013); (c) Thong & Chi (2014); (d) Chi et al. (2014); (e) chloroform-d1.
Cytotoxic effects of the examined compounds (IC50a in µM) and some reference compounds top
CompoundKBLUHep-G2MCF-7
trans-[PtCl2(Preug)(Qui)] (2)4.27±0.097.02±0.286.64±0.206.47±0.32
trans-[PtCl2(iPreug)(Qui)] (3)5.09±0.184.64±0.125.96±0.305.93±0.12
[PtCl(Qui-O)(Preug)] (4)0.39±0.021.25±0.051.99±0.101.55±0.06
[PtCl(Qui-O)(iPreug)] (5)0.41±0.010.44±0.020.38±0.010.61±0.03
[PtCl(Qui-COO)(Preug)] (6)7.27±0.3218.60±0.3714.68±0.4529.23±1.24
Ellipcitine1.26±0.031.42±0.072.15±0.091.83±0.06
[PtCl(Qui-O)(olefin)]b0.43-1.392.95-8.175.29–9.581.84–9.04
Other PtII5.98-22.54c3.4–85.37d4.65–90.79e
Qui-OHf37.8962.9643.5440.37
Cisplating15.242.913.345.7
Notes: (a) IC50 is the concentration of the compound required to inhibit cell growth by 50%. Mean values of IC50 (in µM) ±S.D. from three experiments are presented. References: (b) Chi et al. (2017a) and Da et al. (2015); (c) Li et al. (2013); (d) Qin et al. (2015), Liu et al. (2014), Fang et al. (2016) and Meng et al. (2016); (e) Nakatake et al. (2011), Liu et al. (2014) and Abu-Safieh et al. (2016); (f) Da et al. (2015); (g) Chi et al. (2017a).
 

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