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The title tetracyclic compound, C29H40O7, has been obtained unexpectedly in a synthetic study of the natural diterpenoid, paclitaxel. There is an intramolecular O—H...O hydrogen bond between the hydroxy and benzyl­oxy groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019871/wn6183sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019871/wn6183Isup2.hkl
Contains datablock I

CCDC reference: 225715

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.042
  • wR factor = 0.126
  • Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C29 PLAT410_ALERT_2_C Short Intra H...H Contact H14A .. H21 = 1.96 Ang. PLAT412_ALERT_2_C Short Intra XH3 .. XHn H10 .. H27C = 1.80 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 3419 Count of symmetry unique reflns 3425 Completeness (_total/calc) 99.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C29H40O7Dx = 1.260 Mg m3
Mr = 500.63Melting point = 427–430 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.7107 Å
a = 13.754 (2) ÅCell parameters from 25 reflections
b = 21.026 (7) Åθ = 10.0–11.2°
c = 9.1287 (10) ŵ = 0.09 mm1
V = 2639.9 (10) Å3T = 297 K
Z = 4Prismatic, colourless
F(000) = 10800.50 × 0.40 × 0.40 mm
Data collection top
Rigaku AFC7R
diffractometer
θmax = 27.5°
ω scansh = 717
4059 measured reflectionsk = 027
3419 independent reflectionsl = 114
2443 reflections with I > 2σ(I)3 standard reflections every 150 reflections
Rint = 0.016 intensity decay: 0.8%
Refinement top
Refinement on F2H-atom parameters not refined
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0632P)2 + 0.271P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.126(Δ/σ)max = 0.002
S = 1.02Δρmax = 0.20 e Å3
3419 reflectionsΔρmin = 0.17 e Å3
326 parametersAbsolute structure: see text
Special details top

Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4180 (2)0.2820 (1)0.3995 (3)0.0664 (6)
O20.4702 (2)0.1833 (1)0.3851 (2)0.0613 (6)
O30.3901 (2)0.2148 (2)0.5844 (3)0.0860 (8)
O40.6455 (2)0.2327 (1)0.1698 (3)0.0588 (6)
O50.5992 (1)0.10974 (9)0.2254 (2)0.0433 (4)
O60.3386 (1)0.11548 (9)0.2367 (2)0.0520 (5)
O70.2929 (2)0.0140 (1)0.3211 (3)0.0724 (7)
C80.4230 (3)0.2259 (2)0.4671 (4)0.0622 (8)
C90.4620 (2)0.2795 (1)0.2537 (3)0.0491 (6)
C100.4998 (2)0.2098 (1)0.2455 (3)0.0443 (6)
C110.5534 (2)0.2293 (1)0.0973 (3)0.0424 (6)
C120.5327 (2)0.2977 (1)0.0357 (3)0.0468 (6)
C130.4212 (2)0.3063 (1)0.0075 (4)0.0540 (7)
C140.3824 (2)0.2948 (1)0.1479 (4)0.0530 (7)
C150.5961 (2)0.3157 (1)0.0968 (4)0.0530 (7)
C160.5471 (2)0.3270 (2)0.2451 (4)0.0627 (8)
C170.5548 (3)0.3438 (2)0.1628 (4)0.0699 (10)
C180.6917 (2)0.3225 (2)0.0812 (5)0.079 (1)
C190.5090 (3)0.3966 (2)0.2480 (6)0.091 (1)
C200.6153 (3)0.3187 (3)0.3753 (5)0.095 (1)
C210.4679 (2)0.1678 (1)0.1152 (3)0.0363 (5)
C220.4318 (2)0.1025 (1)0.1712 (3)0.0437 (6)
C230.4185 (2)0.0534 (1)0.0515 (3)0.0488 (7)
C240.5082 (2)0.0492 (1)0.0441 (3)0.0477 (6)
C250.5237 (2)0.1131 (1)0.1149 (3)0.0399 (5)
C260.5502 (2)0.1660 (1)0.0034 (3)0.0368 (5)
C270.6497 (2)0.1502 (2)0.0652 (3)0.0487 (7)
C280.5638 (2)0.0862 (2)0.3620 (3)0.0586 (8)
C290.6463 (2)0.0791 (1)0.4679 (3)0.0477 (6)
C300.6585 (3)0.0233 (2)0.5438 (4)0.0707 (10)
C310.7316 (4)0.0159 (2)0.6453 (5)0.088 (1)
C320.7953 (3)0.0644 (2)0.6707 (4)0.077 (1)
C330.7848 (3)0.1201 (2)0.5976 (4)0.078 (1)
C340.7105 (3)0.1276 (2)0.4969 (4)0.0647 (9)
C350.3150 (3)0.0771 (2)0.3575 (4)0.0696 (10)
C360.2085 (3)0.0077 (2)0.2331 (6)0.085 (1)
H40.65720.19860.20950.0588*
H100.56890.21150.24500.0530*
H110.50720.22310.17320.0502*
H13A0.40530.34890.03310.0641*
H13B0.38820.27780.07080.0641*
H14A0.33780.26030.14550.0626*
H14B0.34980.33210.18050.0626*
H17A0.62210.34150.18660.0835*
H17B0.51730.33220.24590.0835*
H17C0.53900.38590.13400.0835*
H18A0.73050.33450.16310.0949*
H18B0.72140.31530.01110.0949*
H19A0.56180.42500.23310.1083*
H19B0.46250.40220.17220.1083*
H19C0.47970.40500.34000.1083*
H20A0.64140.27680.37480.1136*
H20B0.66690.34860.36920.1136*
H20C0.58030.32520.46400.1136*
H210.41360.18820.07160.0430*
H220.47530.08680.24360.0522*
H23A0.40700.01310.09510.0582*
H23B0.36460.06500.00740.0582*
H24A0.56320.03820.01380.0570*
H24B0.49900.01760.11760.0570*
H250.46490.12490.16170.0480*
H27A0.64580.11040.11440.0580*
H27B0.69750.14790.00950.0580*
H27C0.66690.18240.13330.0580*
H28A0.53360.04610.34730.0701*
H28B0.51750.11530.40080.0701*
H300.61540.01120.52540.0844*
H310.73750.02280.69820.1046*
H320.84710.05900.73870.0920*
H330.82860.15400.61540.0932*
H340.70370.16700.44680.0776*
H35A0.36900.07690.42280.0828*
H35B0.26030.09510.40540.0828*
H36A0.15380.02390.28480.1031*
H36B0.21690.03110.14490.1031*
H36C0.19810.03580.21060.1031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.074 (1)0.068 (1)0.057 (1)0.007 (1)0.023 (1)0.014 (1)
O20.081 (1)0.071 (1)0.0322 (10)0.016 (1)0.003 (1)0.0019 (10)
O30.093 (2)0.119 (2)0.046 (1)0.011 (2)0.014 (1)0.003 (1)
O40.057 (1)0.057 (1)0.063 (1)0.010 (1)0.026 (1)0.008 (1)
O50.0407 (9)0.057 (1)0.0327 (9)0.0016 (8)0.0008 (8)0.0063 (8)
O60.051 (1)0.058 (1)0.048 (1)0.0045 (9)0.0155 (10)0.0086 (10)
O70.075 (2)0.067 (2)0.075 (2)0.002 (1)0.013 (1)0.028 (1)
C80.065 (2)0.080 (2)0.041 (2)0.006 (2)0.003 (2)0.010 (2)
C90.047 (1)0.054 (2)0.046 (1)0.001 (1)0.010 (1)0.014 (1)
C100.039 (1)0.060 (2)0.034 (1)0.003 (1)0.001 (1)0.006 (1)
C110.039 (1)0.048 (1)0.040 (1)0.005 (1)0.000 (1)0.000 (1)
C120.047 (1)0.044 (1)0.050 (2)0.002 (1)0.005 (1)0.001 (1)
C130.049 (2)0.048 (2)0.065 (2)0.007 (1)0.002 (2)0.006 (1)
C140.043 (1)0.044 (1)0.072 (2)0.006 (1)0.008 (1)0.002 (1)
C150.047 (2)0.049 (2)0.063 (2)0.008 (1)0.006 (1)0.014 (1)
C160.060 (2)0.063 (2)0.065 (2)0.013 (2)0.006 (2)0.023 (2)
C170.084 (2)0.054 (2)0.072 (2)0.005 (2)0.019 (2)0.011 (2)
C180.049 (2)0.099 (3)0.090 (3)0.023 (2)0.009 (2)0.034 (2)
C190.096 (3)0.059 (2)0.118 (3)0.017 (2)0.036 (3)0.036 (2)
C200.084 (3)0.132 (4)0.069 (2)0.033 (3)0.009 (2)0.033 (3)
C210.033 (1)0.043 (1)0.033 (1)0.007 (1)0.002 (1)0.001 (1)
C220.045 (1)0.050 (1)0.037 (1)0.004 (1)0.003 (1)0.008 (1)
C230.056 (2)0.042 (1)0.049 (2)0.002 (1)0.009 (1)0.002 (1)
C240.054 (2)0.041 (1)0.048 (2)0.003 (1)0.005 (1)0.003 (1)
C250.037 (1)0.047 (1)0.035 (1)0.004 (1)0.002 (1)0.001 (1)
C260.032 (1)0.045 (1)0.034 (1)0.0021 (10)0.001 (1)0.002 (1)
C270.037 (1)0.067 (2)0.043 (1)0.008 (1)0.004 (1)0.008 (1)
C280.057 (2)0.081 (2)0.037 (1)0.004 (2)0.004 (1)0.009 (1)
C290.050 (1)0.062 (2)0.031 (1)0.006 (1)0.006 (1)0.003 (1)
C300.105 (3)0.054 (2)0.053 (2)0.002 (2)0.013 (2)0.003 (2)
C310.128 (4)0.072 (3)0.062 (2)0.036 (3)0.022 (3)0.010 (2)
C320.067 (2)0.113 (3)0.051 (2)0.029 (2)0.005 (2)0.003 (2)
C330.065 (2)0.121 (3)0.049 (2)0.025 (2)0.001 (2)0.012 (2)
C340.076 (2)0.073 (2)0.046 (2)0.012 (2)0.009 (2)0.017 (2)
C350.071 (2)0.090 (3)0.047 (2)0.003 (2)0.016 (2)0.013 (2)
C360.082 (3)0.084 (3)0.090 (3)0.020 (2)0.016 (3)0.019 (2)
Geometric parameters (Å, º) top
O1—C81.333 (4)C19—H19C0.949
O1—C91.462 (4)C20—H20A0.952
O2—C81.334 (4)C20—H20B0.949
O2—C101.449 (4)C20—H20C0.951
O3—C81.186 (4)C21—C221.545 (4)
O4—C111.431 (3)C21—C261.567 (3)
O4—H40.820C21—H210.950
O5—C251.449 (3)C22—C231.515 (4)
O5—C281.427 (4)C22—H220.951
O6—C221.441 (3)C23—C241.514 (4)
O6—C351.405 (4)C23—H23A0.948
O7—C351.400 (5)C23—H23B0.948
O7—C361.418 (5)C24—C251.507 (4)
C9—C101.556 (4)C24—H24A0.950
C9—C141.495 (4)C24—H24B0.952
C9—C161.542 (4)C25—C261.552 (4)
C10—C211.545 (4)C25—H250.948
C10—H100.951C26—C271.542 (4)
C11—C121.571 (4)C27—H27A0.950
C11—C261.582 (4)C27—H27B0.948
C11—H110.949C27—H27C0.950
C12—C131.566 (4)C28—C291.498 (4)
C12—C151.538 (4)C28—H28A0.950
C12—C171.542 (5)C28—H28B0.951
C13—C141.535 (5)C29—C301.374 (4)
C13—H13A0.950C29—C341.375 (5)
C13—H13B0.948C30—C311.376 (6)
C14—H14A0.950C30—H300.951
C14—H14B0.950C31—C321.363 (7)
C15—C161.531 (5)C31—H310.951
C15—C181.331 (4)C32—C331.356 (7)
C16—C191.554 (5)C32—H320.952
C16—C201.525 (6)C33—C341.384 (5)
C17—H17A0.951C33—H330.948
C17—H17B0.949C34—H340.949
C17—H17C0.950C35—H35A0.952
C18—H18A0.952C35—H35B0.949
C18—H18B0.948C36—H36A0.951
C19—H19A0.950C36—H36B0.950
C19—H19B0.950C36—H36C0.950
C8—O1—C9111.6 (2)C10—C21—H21106.7
C8—O2—C10111.8 (2)C22—C21—C26116.1 (2)
C11—O4—H4109.5C22—C21—H21106.7
C25—O5—C28112.4 (2)C26—C21—H21106.8
C22—O6—C35115.1 (2)O6—C22—C21104.8 (2)
C35—O7—C36113.6 (3)O6—C22—C23108.7 (2)
O1—C8—O2111.0 (3)O6—C22—H22109.7
O1—C8—O3124.9 (4)C21—C22—C23114.0 (2)
O2—C8—O3124.1 (4)C21—C22—H22109.7
O1—C9—C10102.5 (2)C23—C22—H22109.8
O1—C9—C14106.1 (2)C22—C23—C24110.9 (2)
O1—C9—C16109.7 (3)C22—C23—H23A109.1
C10—C9—C14114.6 (2)C22—C23—H23B109.0
C10—C9—C16110.7 (2)C24—C23—H23A109.0
C14—C9—C16112.5 (3)C24—C23—H23B109.0
O2—C10—C9103.0 (2)H23A—C23—H23B109.7
O2—C10—C21112.1 (2)C23—C24—C25108.1 (2)
O2—C10—H10107.4C23—C24—H24A110.0
C9—C10—C21118.7 (2)C23—C24—H24B109.7
C9—C10—H10107.4C25—C24—H24A110.0
C21—C10—H10107.5C25—C24—H24B109.8
O4—C11—C12106.2 (2)H24A—C24—H24B109.3
O4—C11—C26108.6 (2)O5—C25—C24110.9 (2)
O4—C11—H11105.2O5—C25—C26108.9 (2)
C12—C11—C26124.8 (2)O5—C25—H25108.1
C12—C11—H11105.3C24—C25—C26113.1 (2)
C26—C11—H11105.2C24—C25—H25107.9
C11—C12—C13110.0 (2)C26—C25—H25107.9
C11—C12—C15113.8 (2)C11—C26—C21112.0 (2)
C11—C12—C17105.7 (2)C11—C26—C25104.7 (2)
C13—C12—C15113.4 (3)C11—C26—C27112.1 (2)
C13—C12—C17104.2 (3)C21—C26—C25107.5 (2)
C15—C12—C17109.0 (2)C21—C26—C27111.4 (2)
C12—C13—C14118.3 (3)C25—C26—C27108.6 (2)
C12—C13—H13A107.1C26—C27—H27A109.4
C12—C13—H13B107.2C26—C27—H27B109.5
C14—C13—H13A107.2C26—C27—H27C109.4
C14—C13—H13B107.3H27A—C27—H27B109.6
H13A—C13—H13B109.6H27A—C27—H27C109.4
C9—C14—C13112.1 (2)H27B—C27—H27C109.6
C9—C14—H14A108.8O5—C28—C29109.9 (2)
C9—C14—H14B108.8O5—C28—H28A109.4
C13—C14—H14A108.8O5—C28—H28B109.3
C13—C14—H14B108.9C29—C28—H28A109.4
H14A—C14—H14B109.4C29—C28—H28B109.4
C12—C15—C16118.9 (3)H28A—C28—H28B109.3
C12—C15—C18120.2 (3)C28—C29—C30120.2 (3)
C16—C15—C18120.8 (3)C28—C29—C34122.4 (3)
C9—C16—C15106.2 (3)C30—C29—C34117.3 (3)
C9—C16—C19110.7 (3)C29—C30—C31121.7 (3)
C9—C16—C20110.7 (3)C29—C30—H30119.1
C15—C16—C19108.0 (3)C31—C30—H30119.3
C15—C16—C20113.6 (3)C30—C31—C32120.0 (4)
C19—C16—C20107.6 (3)C30—C31—H31120.0
C12—C17—H17A109.4C32—C31—H31119.9
C12—C17—H17B109.5C31—C32—C33119.5 (4)
C12—C17—H17C109.4C31—C32—H32120.3
H17A—C17—H17B109.5C33—C32—H32120.2
H17A—C17—H17C109.4C32—C33—C34120.4 (4)
H17B—C17—H17C109.6C32—C33—H33119.8
C15—C18—H18A119.9C34—C33—H33119.8
C15—C18—H18B120.1C29—C34—C33121.1 (3)
H18A—C18—H18B120.0C29—C34—H34119.4
C16—C19—H19A109.4C33—C34—H34119.5
C16—C19—H19B109.3O6—C35—O7114.1 (3)
C16—C19—H19C109.5O6—C35—H35A108.2
H19A—C19—H19B109.5O6—C35—H35B108.3
H19A—C19—H19C109.6O7—C35—H35A108.4
H19B—C19—H19C109.6O7—C35—H35B108.5
C16—C20—H20A109.5H35A—C35—H35B109.3
C16—C20—H20B109.8O7—C36—H36A109.4
C16—C20—H20C109.6O7—C36—H36B109.5
H20A—C20—H20B109.4O7—C36—H36C109.5
H20A—C20—H20C109.2H36A—C36—H36B109.4
H20B—C20—H20C109.4H36A—C36—H36C109.4
C10—C21—C22110.2 (2)H36B—C36—H36C109.5
C10—C21—C26109.9 (2)
O1—C8—O2—C101.5 (4)C11—C12—C13—C1496.0 (3)
O1—C9—C10—O21.1 (3)C11—C12—C15—C16115.4 (3)
O1—C9—C10—C21125.7 (2)C11—C12—C15—C1866.1 (4)
O1—C9—C14—C13169.3 (2)C11—C26—C21—C22157.4 (2)
O1—C9—C16—C15173.4 (2)C11—C26—C25—C24174.9 (2)
O1—C9—C16—C1969.6 (4)C12—C11—C26—C2136.3 (3)
O1—C9—C16—C2049.6 (4)C12—C11—C26—C25152.5 (2)
O2—C8—O1—C92.3 (4)C12—C11—C26—C2789.9 (3)
O2—C10—C9—C14113.4 (3)C12—C15—C16—C1983.4 (3)
O2—C10—C9—C16118.0 (3)C12—C15—C16—C20157.4 (3)
O2—C10—C21—C2211.5 (3)C13—C12—C11—C2673.8 (3)
O2—C10—C21—C26140.7 (2)C13—C12—C15—C1611.4 (4)
O3—C8—O1—C9177.6 (3)C13—C12—C15—C18167.1 (3)
O3—C8—O2—C10178.4 (3)C13—C14—C9—C1649.3 (3)
O4—C11—C12—C13158.9 (2)C14—C9—C10—C2111.2 (4)
O4—C11—C12—C1572.6 (3)C14—C9—C16—C1568.7 (3)
O4—C11—C12—C1747.0 (3)C14—C9—C16—C1948.3 (4)
O4—C11—C26—C21162.6 (2)C14—C9—C16—C20167.5 (3)
O4—C11—C26—C2581.2 (2)C14—C13—C12—C1532.7 (3)
O4—C11—C26—C2736.4 (3)C14—C13—C12—C17151.1 (3)
O5—C25—C24—C23171.0 (2)C15—C12—C11—C2654.7 (3)
O5—C25—C26—C1161.4 (2)C16—C9—C10—C21117.4 (3)
O5—C25—C26—C21179.3 (2)C16—C15—C12—C17126.9 (3)
O5—C25—C26—C2758.6 (3)C17—C12—C11—C26174.3 (2)
O5—C28—C29—C30130.1 (3)C17—C12—C15—C1851.6 (4)
O5—C28—C29—C3451.9 (4)C18—C15—C16—C1995.2 (4)
O6—C22—C21—C1073.2 (2)C18—C15—C16—C2024.1 (5)
O6—C22—C21—C26161.2 (2)C21—C22—O6—C35147.2 (2)
O6—C22—C23—C24166.8 (2)C21—C22—C23—C2450.3 (3)
O6—C35—O7—C3664.1 (4)C21—C26—C25—C2455.6 (3)
O7—C35—O6—C2271.9 (3)C22—C21—C26—C2542.9 (3)
C8—O1—C9—C102.0 (3)C22—C21—C26—C2776.0 (3)
C8—O1—C9—C14118.5 (3)C22—C23—C24—C2561.2 (3)
C8—O1—C9—C16119.7 (3)C23—C22—O6—C3590.6 (3)
C8—O2—C10—C90.2 (3)C23—C22—C21—C2642.4 (3)
C8—O2—C10—C21128.6 (3)C23—C24—C25—C2666.4 (3)
C9—C10—C21—C22131.6 (2)C24—C25—O5—C2882.2 (3)
C9—C10—C21—C2699.3 (3)C24—C25—C26—C2765.1 (3)
C9—C14—C13—C122.8 (4)C25—O5—C28—C29175.6 (2)
C9—C16—C15—C1235.4 (4)C26—C25—O5—C28152.8 (2)
C9—C16—C15—C18146.0 (3)C28—C29—C30—C31177.8 (4)
C10—C9—C14—C1378.3 (3)C28—C29—C34—C33178.6 (3)
C10—C9—C16—C1561.1 (3)C29—C30—C31—C321.3 (6)
C10—C9—C16—C19178.1 (3)C29—C34—C33—C320.4 (5)
C10—C9—C16—C2062.7 (4)C30—C29—C34—C330.6 (5)
C10—C21—C22—C23168.1 (2)C30—C31—C32—C331.4 (6)
C10—C21—C26—C1176.8 (2)C31—C30—C29—C340.3 (5)
C10—C21—C26—C25168.7 (2)C31—C32—C33—C340.6 (6)
C10—C21—C26—C2749.8 (3)C31—C32—C33—C340.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O50.822.042.711 (2)139
 

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