Download citation
Download citation
link to html
Reaction of acetyl chloride with [Pt(Cl2Fc)(CH3)(bipy)], where Cl2Fc and bipy are 1,1'-di­chloro­ferrocen-2-yl and 2,2'-bi­pyridine, respectively, results in the trans oxidative-addition of the acetyl chloride to the PtII precursor to give the PtIV title compound, i.e. [Pt(CH3)(C2H3O)(C10H7Cl2Fe)Cl(C10H8N2)]. The three Pt-C bonds in the title compound are in a fac-configuration and range in length from 2.018 (12) to 2.079 (11) Å. The chloro substituents of the ferrocenyl unit are in an eclipsed conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801009862/na6087sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801009862/na6087Isup2.hkl
Contains datablock I

CCDC reference: 170746

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.018 Å
  • R factor = 0.054
  • wR factor = 0.135
  • Data-to-parameter ratio = 15.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.034 0.124 Tmin and Tmax expected: 0.115 0.489 RR = 1.165 Please check that your absorption correction is appropriate. General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 3.944 Tmax scaled 0.489 Tmin scaled 0.134 REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 4453 From the CIF: _diffrn_reflns_limit_ max hkl 13. 19. 22. From the CIF: _diffrn_reflns_limit_ min hkl -14. 0. 0. TEST1: Expected hkl limits for theta max Calculated maximum hkl 12. 17. 19. Calculated minimum hkl -12. -17. -19. ALERT: Expected hkl max differ from CIF values
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The title compound, (I), was prepared during a study of the reactivity in oxidative-addition reactions of the 16-electron complex [Pt(Cl2Fc)(CH3)(bipy)]. The structure determination of (I) (Fig. 1), shows that the three Pt—C bonds are in the fac configuration and that the acetyl chloride has undergone trans addition to the PtII precursor. The Pt—C bond lengths are 2.018 (12), 2.027 (10) and 2.079 (11) Å for acetyl, ferrocenyl and methyl groups, respectively. The conformation of the ferrocenyl group is that of an eclipsed geometry in which the chlorine substituents also eclipse one another: the two chlorines are twisted about the line joining the two ring centroids by only -1.8 (9)°. The Fe centre lies 1.650 (5) Å out of the C1—C5 plane and 1.645 (5) Å from the C6—C10 plane, with a centroid–Fe–centroid angle of 173.7 (3)°.

The chlorine substituents are displaced outwards from their respective ring planes, Cl1 by 0.09 (2) Å and Cl2 by 0.12 (2) Å. The two rings are inclined at an angle of 7.1 (9)°, with the longest inter-ring distances involving separations between corresponding atoms [C1···C6 3.406 (15) and C2···C7 3.416 (14) Å] where at least one of these carries a substituent. These parameters suggest a small but significant degree of repulsion between the two rings.

Although individual molecules have chiral centres at Pt and at the Cl2Fc ligand the single-crystal selected was found to be racemic.

Experimental top

[Pt(Cl2Fc)(CH3)(1,5-cyclooctadiene)] (2.52 g, 4.41 mmol) (Hollands et al., 1985) was dissolved in benzene (40 ml) and a solution of bipy (1.51 g, 9.68 mmol) in benzene (10 ml) was added. The solution was heated under reflux for 6 h and then allowed to cool. Brown crystals of [Pt(Cl2Fc)(CH3)(bipy)] were isolated by filtration. Yield 2.65 g (97%). [Pt(Cl2Fc)(CH3)(bipy)] (0.18 g, 0.29 mmol) was dissolved in dichloromethane (40 ml) and acetyl chloride (0.07 ml, 1.02 mmol) was added. The solution was stirred for 1 h. Evaporation of the solvent, column chromatography of the residue on alumina and elution with benzene/chloroform (1:1) produced firstly unreacted material and secondly an orange oil. Crystallization of the oil from dichloromethane/hexane produced the pure title compound as orange–red crystals. Yield 0.12 g (58%).

Refinement top

Due to the relative weakness of the higher-angle data, only reflections with 2θ 52° were included in the refinement: the corresponding index limits are -12 h 12, 0 k 17, 0 l 19. Methyl H atoms were located from ΔF syntheses while others were placed geometrically. In refinement, methyl groups were constrained to be rigid rotating groups with C—H distances at 0.96 Å and with Uiso(H) = 1.5Ueq(C). Other H atoms were constrained to ride at 0.93 Å from their carrier atoms with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: DIF4 (Stoe & Cie, 1987); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 and PLATON.

Figures top
[Figure 1] Fig. 1. A view of the title compound showing atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
(I) top
Crystal data top
[Pt(CH3)(C2H3O)(C10H7Cl2Fe)Cl(C10H8N2)]F(000) = 1344
Mr = 698.71Dx = 2.041 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
a = 10.0991 (11) ÅCell parameters from 80 reflections
b = 14.1486 (15) Åθ = 15–16°
c = 16.205 (3) ŵ = 7.15 mm1
β = 100.85 (1)°T = 298 K
V = 2274.1 (5) Å3Plate, orange
Z = 40.33 × 0.33 × 0.10 mm
Data collection top
Stoe Stadi-4 four-circle
diffractometer
3164 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 26.0°, θmin = 1.9°
ω/2θ scansh = 1413
Absorption correction: ψ scan
North et al., 1968
k = 019
Tmin = 0.034, Tmax = 0.124l = 022
7096 measured reflections3 standard reflections every 60 min
4453 independent reflections intensity decay: 5.0%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: see text
wR(F2) = 0.135See text
S = 1.04 w = 1/[σ2(Fo2) + (0.075P)2 + 3.92P]
where P = (Fo2 + 2Fc2)/3
4453 reflections(Δ/σ)max = 0.002
282 parametersΔρmax = 1.52 e Å3
175 restraintsΔρmin = 1.54 e Å3
Crystal data top
[Pt(CH3)(C2H3O)(C10H7Cl2Fe)Cl(C10H8N2)]V = 2274.1 (5) Å3
Mr = 698.71Z = 4
Monoclinic, P21/aMo Kα radiation
a = 10.0991 (11) ŵ = 7.15 mm1
b = 14.1486 (15) ÅT = 298 K
c = 16.205 (3) Å0.33 × 0.33 × 0.10 mm
β = 100.85 (1)°
Data collection top
Stoe Stadi-4 four-circle
diffractometer
3164 reflections with I > 2σ(I)
Absorption correction: ψ scan
North et al., 1968
Rint = 0.016
Tmin = 0.034, Tmax = 0.1243 standard reflections every 60 min
7096 measured reflections intensity decay: 5.0%
4453 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.054175 restraints
wR(F2) = 0.135See text
S = 1.04Δρmax = 1.52 e Å3
4453 reflectionsΔρmin = 1.54 e Å3
282 parameters
Special details top

Experimental. Unit-cell refinement was based on theta values measured at ±ω.

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.5832 (0.0384) x - 8.8877 (0.0634) y + 0.9554 (0.0873) z = 1.6433 (0.0096)

* 0.0008 (0.0017) C1 * -0.0001 (0.0009) C2 * -0.0006 (0.0017) C3 * 0.0011 (0.0025) C4 * -0.0011 (0.0024) C5 1.6504 (0.0049) Fe -0.0868 (0.0172) Cl1

Rms deviation of fitted atoms = 0.0008

7.0187 (0.0470) x - 10.0131 (0.0645) y - 0.0976 (0.0975) z = 4.7692 (0.0123)

Angle to previous plane (with approximate e.s.d.) = 7.11 (0.86)

* -0.0007 (0.0018) C6 * 0.0002 (0.0009) C7 * 0.0004 (0.0018) C8 * -0.0008 (0.0026) C9 * 0.0009 (0.0026) C10 - 1.6447 (0.0054) Fe 0.1150 (0.0198) Cl2

Rms deviation of fitted atoms = 0.0007

0.7155 (0.0614) x - 13.3589 (0.0261) y + 4.9041 (0.0856) z = 0.9557 (0.0438)

Angle to previous plane (with approximate e.s.d.) = 40.68 (0.52)

* 0.0008 (0.0017) N1 * -0.0006 (0.0010) C11 * -0.0004 (0.0022) C12 * 0.0012 (0.0037) C13 * -0.0010 (0.0027) C14 0.0078 (0.0072) C15

Rms deviation of fitted atoms = 0.0009

0.7555 (0.0458) x - 13.1386 (0.0283) y + 5.5558 (0.0828) z = 1.3600 (0.0364)

Angle to previous plane (with approximate e.s.d.) = 2.56 (0.51)

* 0.0013 (0.0016) N2 * -0.0007 (0.0010) C16 * -0.0011 (0.0021) C17 * 0.0023 (0.0035) C18 * -0.0018 (0.0025) C19 0.0092 (0.0068) C20

Rms deviation of fitted atoms = 0.0015

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pt0.18726 (4)0.04385 (3)0.29401 (3)0.03735 (14)
C1A0.1835 (12)0.1795 (8)0.2550 (8)0.053 (2)
O1A0.2650 (11)0.2339 (6)0.2924 (6)0.073 (2)
C2A0.0775 (14)0.2117 (12)0.1824 (11)0.088 (4)
H2A10.08950.27780.17240.132*
H2A20.01030.20150.19540.132*
H2A30.08580.17640.13300.132*
Cl30.2014 (3)0.1192 (2)0.35458 (18)0.0515 (6)
C1M0.0213 (10)0.0302 (10)0.2658 (9)0.067 (3)
H1M10.04960.01920.20670.100*
H1M20.06230.08720.28120.100*
H1M30.04840.02200.29660.100*
N10.1892 (10)0.0925 (6)0.4193 (6)0.0536 (18)
C110.0818 (14)0.0999 (7)0.4548 (9)0.068 (3)
H110.00220.08400.42360.082*
C120.0905 (19)0.1303 (8)0.5366 (10)0.091 (4)
H120.01370.13500.56040.109*
C130.220 (2)0.1545 (8)0.5838 (9)0.094 (5)
H130.23060.17520.63910.113*
C140.3258 (18)0.1459 (8)0.5445 (9)0.086 (4)
H140.41120.16180.57370.104*
C150.3128 (13)0.1145 (6)0.4627 (7)0.052 (2)
N20.3975 (8)0.0639 (5)0.3421 (6)0.0409 (16)
C160.4273 (11)0.0988 (6)0.4202 (7)0.045 (2)
C170.5595 (12)0.1216 (7)0.4561 (9)0.067 (3)
H170.57880.14590.51040.080*
C180.6600 (12)0.1089 (7)0.4130 (9)0.066 (3)
H180.74840.12390.43730.079*
C190.6298 (11)0.0732 (7)0.3320 (8)0.056 (3)
H190.69680.06450.30050.067*
C200.4974 (10)0.0512 (7)0.2998 (7)0.049 (2)
H200.47660.02610.24580.059*
Fe0.29052 (14)0.10960 (11)0.12200 (10)0.0397 (3)
C10.2352 (8)0.0272 (7)0.1071 (6)0.0381 (14)
C20.1858 (8)0.0074 (7)0.1770 (6)0.0355 (13)
C30.1010 (8)0.0836 (7)0.1407 (7)0.0439 (16)
H30.05190.12210.17040.053*
C40.1015 (10)0.0925 (8)0.0555 (7)0.0541 (19)
H40.05380.13730.01980.065*
C50.1849 (10)0.0235 (8)0.0326 (7)0.0513 (17)
H50.20390.01280.02060.062*
Cl10.3400 (3)0.1265 (2)0.1071 (2)0.0570 (7)
C60.4905 (11)0.1338 (9)0.1382 (8)0.060 (2)
C70.4435 (10)0.1675 (8)0.2080 (8)0.0542 (18)
H70.47120.14860.26360.065*
C80.3451 (12)0.2361 (8)0.1773 (9)0.062 (2)
H80.29580.27110.20960.074*
C90.3342 (13)0.2429 (9)0.0903 (9)0.069 (2)
H90.27620.28300.05500.082*
C100.4254 (12)0.1788 (9)0.0647 (9)0.069 (2)
H100.43950.16860.01030.083*
Cl20.6232 (4)0.0523 (3)0.1395 (3)0.0909 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt0.0374 (2)0.0366 (2)0.0392 (2)0.00248 (18)0.01026 (14)0.0022 (2)
C1A0.063 (5)0.042 (3)0.055 (6)0.019 (3)0.018 (4)0.003 (3)
O1A0.113 (7)0.034 (4)0.073 (7)0.002 (4)0.021 (5)0.003 (4)
C2A0.078 (9)0.087 (10)0.096 (11)0.048 (7)0.010 (5)0.032 (7)
Cl30.0677 (16)0.0420 (15)0.0442 (17)0.0060 (12)0.0090 (13)0.0049 (12)
C1M0.030 (3)0.095 (8)0.077 (7)0.009 (4)0.015 (3)0.001 (6)
N10.067 (4)0.050 (4)0.049 (4)0.003 (4)0.025 (3)0.006 (4)
C110.087 (5)0.066 (9)0.065 (7)0.009 (7)0.046 (5)0.001 (6)
C120.158 (9)0.051 (8)0.087 (9)0.013 (9)0.082 (8)0.018 (8)
C130.190 (12)0.060 (9)0.045 (7)0.017 (10)0.055 (7)0.010 (7)
C140.149 (9)0.065 (9)0.050 (6)0.042 (9)0.031 (6)0.025 (7)
C150.085 (4)0.037 (6)0.036 (4)0.012 (5)0.016 (4)0.001 (4)
N20.039 (3)0.029 (4)0.052 (4)0.002 (3)0.001 (2)0.014 (3)
C160.057 (3)0.032 (6)0.041 (5)0.005 (4)0.003 (3)0.001 (4)
C170.066 (4)0.068 (9)0.054 (7)0.014 (6)0.018 (4)0.005 (6)
C180.048 (5)0.054 (8)0.085 (8)0.019 (5)0.016 (5)0.006 (6)
C190.039 (4)0.053 (7)0.070 (7)0.003 (5)0.003 (4)0.012 (5)
C200.043 (3)0.067 (8)0.036 (5)0.004 (5)0.001 (3)0.008 (5)
Fe0.0440 (7)0.0402 (8)0.0338 (8)0.0023 (6)0.0044 (6)0.0031 (6)
C10.038 (4)0.041 (2)0.034 (3)0.001 (2)0.002 (3)0.003 (3)
C20.029 (4)0.040 (3)0.036 (3)0.001 (2)0.002 (3)0.000 (2)
C30.037 (3)0.045 (5)0.047 (4)0.009 (3)0.001 (3)0.001 (3)
C40.053 (3)0.057 (5)0.043 (4)0.008 (3)0.014 (3)0.005 (4)
C50.062 (5)0.056 (5)0.031 (3)0.002 (3)0.002 (3)0.003 (3)
Cl10.0698 (18)0.0477 (16)0.0535 (19)0.0123 (13)0.0113 (14)0.0108 (14)
C60.051 (3)0.064 (6)0.066 (6)0.016 (3)0.017 (3)0.008 (4)
C70.051 (4)0.054 (6)0.055 (4)0.017 (3)0.001 (3)0.001 (3)
C80.080 (6)0.039 (4)0.062 (5)0.008 (3)0.004 (5)0.003 (4)
C90.089 (6)0.048 (4)0.066 (6)0.011 (3)0.008 (5)0.017 (4)
C100.083 (5)0.067 (6)0.062 (5)0.017 (3)0.027 (4)0.017 (4)
Cl20.0580 (18)0.105 (3)0.120 (3)0.0061 (19)0.045 (2)0.020 (3)
Geometric parameters (Å, º) top
Pt—C1A2.018 (12)C19—C201.376 (15)
Pt—C1M2.079 (11)C19—H190.9300
Pt—C22.027 (10)C20—H200.9300
Pt—N12.140 (10)Fe—C12.017 (9)
Pt—N22.138 (8)Fe—C22.088 (9)
Pt—Cl32.501 (3)Fe—C32.028 (9)
C1A—O1A1.204 (15)Fe—C42.022 (9)
C1A—C2A1.505 (18)Fe—C52.035 (10)
C2A—H2A10.9600Fe—C62.016 (10)
C2A—H2A20.9600Fe—C72.047 (10)
C2A—H2A30.9600Fe—C82.032 (11)
C1M—H1M10.9600Fe—C92.025 (11)
C1M—H1M20.9600Fe—C102.038 (10)
C1M—H1M30.9600C1—C21.409 (13)
N1—C111.324 (14)C1—C51.414 (15)
N1—C151.349 (15)C1—Cl11.758 (10)
C11—C121.38 (2)C2—C31.432 (14)
C11—H110.9300C3—C41.387 (16)
C12—C131.42 (2)C3—H30.9300
C12—H120.9300C4—C51.385 (16)
C13—C141.35 (2)C4—H40.9300
C13—H130.9300C5—H50.9300
C14—C151.380 (17)C6—C71.391 (17)
C14—H140.9300C6—C101.401 (19)
C15—C161.470 (16)C6—Cl21.766 (14)
N2—C201.335 (13)C7—C81.412 (17)
N2—C161.339 (14)C7—H70.9300
C16—C171.390 (15)C8—C91.397 (19)
C17—C181.347 (19)C8—H80.9300
C17—H170.9300C9—C101.409 (19)
C18—C191.386 (19)C9—H90.9300
C18—H180.9300C10—H100.9300
C1A—Pt—C292.9 (4)C20—N2—C16118.6 (9)
C1A—Pt—C1M93.5 (5)C20—N2—Pt126.2 (7)
C2—Pt—C1M86.1 (4)C16—N2—Pt115.1 (7)
C1A—Pt—N287.0 (4)N2—C16—C17120.6 (11)
C2—Pt—N2102.7 (3)N2—C16—C15116.2 (10)
C1M—Pt—N2171.1 (4)C17—C16—C15123.2 (12)
C1A—Pt—N189.3 (4)C18—C17—C16120.7 (13)
C2—Pt—N1177.8 (3)C18—C17—H17119.7
C1M—Pt—N193.8 (5)C16—C17—H17119.7
N2—Pt—N177.3 (4)C17—C18—C19119.1 (11)
C1A—Pt—Cl3175.1 (4)C17—C18—H18120.4
C2—Pt—Cl391.6 (3)C19—C18—H18120.4
C1M—Pt—Cl388.9 (4)C20—C19—C18117.8 (12)
N2—Pt—Cl390.0 (2)C20—C19—H19121.1
N1—Pt—Cl386.2 (2)C18—C19—H19121.1
O1A—C1A—C2A121.1 (13)N2—C20—C19123.3 (11)
O1A—C1A—Pt118.7 (10)N2—C20—H20118.4
C2A—C1A—Pt120.1 (11)C19—C20—H20118.4
C1A—C2A—H2A1109.5C2—C1—C5112.7 (9)
C1A—C2A—H2A2109.5C2—C1—Cl1125.6 (8)
H2A1—C2A—H2A2109.5C5—C1—Cl1121.7 (8)
C1A—C2A—H2A3109.5C1—C2—C3101.9 (9)
H2A1—C2A—H2A3109.5C1—C2—Pt133.3 (7)
H2A2—C2A—H2A3109.5C3—C2—Pt123.5 (7)
Pt—C1M—H1M1109.5C4—C3—C2111.3 (9)
Pt—C1M—H1M2109.5C4—C3—H3124.4
H1M1—C1M—H1M2109.5C2—C3—H3124.4
Pt—C1M—H1M3109.5C5—C4—C3108.6 (10)
H1M1—C1M—H1M3109.5C5—C4—H4125.7
H1M2—C1M—H1M3109.5C3—C4—H4125.7
C11—N1—C15120.5 (12)C4—C5—C1105.5 (10)
C11—N1—Pt125.2 (10)C4—C5—H5127.3
C15—N1—Pt114.3 (7)C1—C5—H5127.3
N1—C11—C12122.2 (15)C7—C6—C10111.0 (12)
N1—C11—H11118.9C7—C6—Cl2126.1 (11)
C12—C11—H11118.9C10—C6—Cl2122.7 (10)
C11—C12—C13118.4 (13)C6—C7—C8105.9 (12)
C11—C12—H12120.8C6—C7—H7127.1
C13—C12—H12120.8C8—C7—H7127.1
C14—C13—C12117.0 (14)C9—C8—C7108.7 (13)
C14—C13—H13121.5C9—C8—H8125.7
C12—C13—H13121.5C7—C8—H8125.7
C13—C14—C15122.7 (16)C8—C9—C10108.7 (13)
C13—C14—H14118.6C8—C9—H9125.6
C15—C14—H14118.6C10—C9—H9125.6
N1—C15—C14119.1 (12)C6—C10—C9105.7 (12)
N1—C15—C16116.9 (10)C6—C10—H10127.1
C14—C15—C16123.9 (12)C9—C10—H10127.1

Experimental details

Crystal data
Chemical formula[Pt(CH3)(C2H3O)(C10H7Cl2Fe)Cl(C10H8N2)]
Mr698.71
Crystal system, space groupMonoclinic, P21/a
Temperature (K)298
a, b, c (Å)10.0991 (11), 14.1486 (15), 16.205 (3)
β (°) 100.85 (1)
V3)2274.1 (5)
Z4
Radiation typeMo Kα
µ (mm1)7.15
Crystal size (mm)0.33 × 0.33 × 0.10
Data collection
DiffractometerStoe Stadi-4 four-circle
diffractometer
Absorption correctionψ scan
North et al., 1968
Tmin, Tmax0.034, 0.124
No. of measured, independent and
observed [I > 2σ(I)] reflections
7096, 4453, 3164
Rint0.016
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.135, 1.04
No. of reflections4453
No. of parameters282
No. of restraints175
H-atom treatmentSee text
Δρmax, Δρmin (e Å3)1.52, 1.54

Computer programs: DIF4 (Stoe & Cie, 1987), DIF4, REDU4 (Stoe & Cie, 1987), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2001), SHELXL97 and PLATON.

 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds