metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 8| August 2011| Pages m1160-m1161

Tetra­kis(μ-4-tert-butyl­benzoato)-κ3O:O,O′;κ3O,O′:O′;κ4O:O′-bis­­[aqua­bis­­(4-tert-butyl­benzoato-κ2O,O′)(4-tert-butyl­benzoic acid-κO)praseodymium(III)]

aInstitute of Safety Science and Engineering, Henan Polytechnic University, Jiaozuo 454003, People's Republic of China, and bDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454003, People's Republic of China
*Correspondence e-mail: yangjuanhpu@yahoo.com

(Received 8 June 2011; accepted 22 July 2011; online 30 July 2011)

The reaction of praseodymium nitrate and 4-tert-butyl­benzoic acid (tBBAH) in aqueous solution yielded the dinuclear title complex, [Pr2(C11H13O2)6(C11H14O2)2(H2O)2], which has non-crystallographic Ci symmetry. The two PrIII ions are linked by two bridging and two bridging–chelating tBBA ligands, with a Pr⋯Pr separation of 4.0817 (9) Å. Each PrIII ion is nine-coordinated by one chelating tBBA ion, one monodentate tBBAH ligand and one water mol­ecule in a distorted tricapped trigonal–prismatic environment. The complex mol­ecules are linked into infinite chains along the c axis by inter­molecular O—H⋯O hydrogen bonds.

Related literature

For the structures and properties of lanthanide benzoate complexes, see: Roh et al. (2005[Roh, S. G., Nah, M. K., Oh, J. B., Baek, N. S., Park, K. M. & Kim, H. K. (2005). Polyhedron, 24, 137-142.]); Singh et al. (2007[Singh, U. P., Kumar, R. & Upreti, S. (2007). J. Mol. Struct. 831, 97-105.]); Xu et al. (2009[Xu, L. J., Li, Y. Q. & Li, X. (2009). J. Rare Earths, 27, 372-375.]); Yang et al. (2010[Yang, J., Li, J. & Wang, Q. (2010). Acta Cryst. E66, m183-m184.]). For bond lengths and angles in other complexes with nine-coordinated PrIII, see: Li et al. (2007[Li, X., Ju, Y. L. & Zhang, T. T. (2007). J. Coord. Chem. 60, 1527-1530.]); Yang et al. (2009[Yang, T.-H., Chen, Q., Zhuang, W., Wang, Z. & Yue, B.-Y. (2009). Acta Cryst. E65, m1152-m1153.]).

[Scheme 1]

Experimental

Crystal data
  • [Pr2(C11H13O2)6(C11H14O2)2(H2O)2]

  • Mr = 1737.58

  • Monoclinic, P 21 /c

  • a = 35.194 (6) Å

  • b = 9.3857 (18) Å

  • c = 27.956 (5) Å

  • β = 107.073 (4)°

  • V = 8827 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.15 mm−1

  • T = 293 K

  • 0.24 × 0.09 × 0.05 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.769, Tmax = 0.841

  • 44864 measured reflections

  • 15556 independent reflections

  • 10611 reflections with I > 2σ(I)

  • Rint = 0.073

Refinement
  • R[F2 > 2σ(F2)] = 0.073

  • wR(F2) = 0.206

  • S = 1.02

  • 15556 reflections

  • 999 parameters

  • 1092 restraints

  • H-atom parameters constrained

  • Δρmax = 5.46 e Å−3

  • Δρmin = −1.00 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2W—H2WB⋯O4i 0.82 2.25 2.824 (8) 127
O2W—H2WA⋯O5i 0.82 1.95 2.759 (8) 167
O1W—H1WA⋯O13ii 0.82 2.50 2.866 (8) 108
O1W—H1WB⋯O10ii 0.82 2.01 2.767 (8) 154
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Lanthanide carboxylate complexes show interesting crystal structures due to the variable coordination number of metal centers as well as coordination versatility of carboxylate ligands. As rigid ligands, benzoic acid and its derivatives have been widely used for lanthanide complexes because they improve the thermal stability and luminescence (Roh et al., 2005; Singh et al., 2007; Xu et al., 2009). In continuation to our research (Yang et al., 2010), we now report the preparation and crystal structure of a new PrIII complex obtained in the reaction with 4-tert-butyl-benzoic acid (tBBAH).

The asymmetric unit of the title dinuclear complex (Fig.1) contains two Pr atoms, six tBBA ligands, two tBBAH ligands and two coordinated water molecules. The title molecule [Pr2(C11H13O2)6(C11H14O2)2(H2O)2] has a non-crystallographic Ci symmetry. The tBBA ligands show four coordination modes: bridging bidentate, chelating bidentate, bridging-chelating tridentate and monodentate mode (tBBAH). The two PrIII ions are linked by four bridging tBBA ligands, with a Pr···Pr seperation of 4.0817 (9) Å. Each PrIII ion is additionally coordinated by one O,O'-bidentate tBBA ion, one monodentate tBBAH ligand and one water molecule. The Pr—O bond lengths are in the range 2.395 (6)-2.807 (6) Å, which is comparable to those reported for other Pr complexes with oxygen environment around the central metal (Li et al., 2007; Yang et al., 2009). Each nine-coordinated PrIII ion adopts a distorted tricapped trigonal-prismatic geometry. The crystal packing is stabilized by intermolecular O—H···O hydrogen bonds (Table 2), which link the molecules into one-dimensional chains along the c axis (Fig.2).

Related literature top

For the structures and properties of lanthanide benzoate complexes, see: Roh et al. (2005); Singh et al. (2007); Xu et al. (2009); Yang et al. (2010). For bond lengths and angles in other complexes with nine-coordinated PrIII, see: Li et al. (2007); Yang et al. (2009).

Experimental top

A mixture of Pr(NO3)3 6H2O (0.226 g, 0.52 mmol), tBBAH (0.150 g, 0.84mmol), melamine (0.026 g, 0.20 mmol) and distilled water (10 ml) was sealed in a 25 ml Teflon-lined stainless autoclave. The mixture was heated at 423 K for 5 days to give the green prism crystals suitable for X-ray diffraction analysis.

M.p.:510.0-511.5 K; Anal. Calcd. for C88H110O18Pr2 (%): C, 60.83; H, 6.34; Pr, 16.24. Found (%): C, 60.62; H, 6.48; Pr, 15.97; Powder X-ray diffraction (PXRD) data are in good agreement with that simulated from the single crystal diffraction data, indicating the high phase purity of as-synthesized. IR (KBr pellet, cm-1): 3433 (νO-H)(br), 2964-2869 (νC-H)(m),1689(νCO(-COOH)(m), 1599 (νC=C)(s), 1550 (νas,-COO)(s), 1399 (νs,-COO)(s), 539 (νPr-O)(w).

Refinement top

All H atoms bound to C atoms were placed in calculated positions and treated in a riding-model approxination, with C—H = 0.93Å and 0.96Å for aryl and methyl type H-atoms, respectively with Uiso = 1.2Ueq(C) or 1.5 Ueq(C). The H-atoms of water molecules were located from difference maps and treated as riding with an idealized distance of O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O). The position of carboxylic H atoms were also located in calculated positions and treated in a riding-model approxination with O-H = 0.82 Å and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, showing the atom-labeling scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level. All the aryl and methyl type H-atoms have been omitted for clarity.
[Figure 2] Fig. 2. The one-dimensional-chain structure of the title compound, viewed along the c axis. Intermolecular hydrogen bonds are shown as dashed lines in blue.
Tetrakis(µ-4-tert-butylbenzoato)- κ3O:O,O';κ3O,O':O'; κ4O:O'-bis[aquabis(4-tert-butylbenzoato- κ2O,O')(4-tert-butylbenzoic acid-κO)praseodymium(III)] top
Crystal data top
[Pr2(C11H13O2)6(C11H14O2)2(H2O)2]F(000) = 3600
Mr = 1737.58Dx = 1.307 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5280 reflections
a = 35.194 (6) Åθ = 2.3–21.5°
b = 9.3857 (18) ŵ = 1.15 mm1
c = 27.956 (5) ÅT = 293 K
β = 107.073 (4)°Prism, green
V = 8827 (3) Å30.24 × 0.09 × 0.05 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
15556 independent reflections
Radiation source: fine-focus sealed tube10611 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
phi and ω scansθmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 3541
Tmin = 0.769, Tmax = 0.841k = 1111
44864 measured reflectionsl = 3233
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.073H-atom parameters constrained
wR(F2) = 0.206 w = 1/[σ2(Fo2) + (0.1044P)2 + 37.5508P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.018
15556 reflectionsΔρmax = 5.46 e Å3
999 parametersΔρmin = 1.00 e Å3
1092 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods
Crystal data top
[Pr2(C11H13O2)6(C11H14O2)2(H2O)2]V = 8827 (3) Å3
Mr = 1737.58Z = 4
Monoclinic, P21/cMo Kα radiation
a = 35.194 (6) ŵ = 1.15 mm1
b = 9.3857 (18) ÅT = 293 K
c = 27.956 (5) Å0.24 × 0.09 × 0.05 mm
β = 107.073 (4)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
15556 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
10611 reflections with I > 2σ(I)
Tmin = 0.769, Tmax = 0.841Rint = 0.073
44864 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0731092 restraints
wR(F2) = 0.206H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1044P)2 + 37.5508P]
where P = (Fo2 + 2Fc2)/3
15556 reflectionsΔρmax = 5.46 e Å3
999 parametersΔρmin = 1.00 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pr10.219711 (13)0.29580 (4)0.368366 (17)0.02660 (15)
Pr20.278908 (14)0.67515 (5)0.394883 (17)0.02809 (15)
O10.17085 (18)0.3021 (7)0.2804 (2)0.0437 (16)
O20.1138 (2)0.1885 (8)0.2729 (3)0.059 (2)
H20.12450.17030.30250.088*
O30.15337 (18)0.1823 (6)0.3664 (2)0.0421 (15)
O40.20493 (17)0.0867 (6)0.4208 (2)0.0359 (14)
O50.28415 (17)0.1920 (6)0.4161 (2)0.0384 (15)
O60.29358 (18)0.4233 (6)0.4144 (2)0.0403 (15)
O70.21606 (19)0.4056 (6)0.4453 (2)0.0423 (15)
O80.24253 (19)0.6234 (6)0.4517 (2)0.0417 (15)
O90.20635 (17)0.5459 (6)0.3495 (2)0.0342 (14)
O100.21380 (17)0.7776 (6)0.3461 (2)0.0381 (14)
O110.25600 (18)0.3470 (6)0.3101 (2)0.0384 (15)
O120.2818 (2)0.5676 (7)0.3191 (2)0.0494 (17)
O130.29395 (17)0.8839 (6)0.3427 (2)0.0375 (14)
O140.34550 (18)0.7831 (7)0.3943 (2)0.0468 (17)
O150.3288 (2)0.6725 (7)0.4825 (2)0.0494 (17)
O160.3870 (2)0.7699 (10)0.4869 (3)0.069 (2)
H160.38530.73360.45970.104*
O1W0.22485 (18)0.0606 (6)0.3258 (2)0.0383 (15)
H1WB0.21960.02450.32200.057*
H1WA0.24490.08330.31800.057*
O2W0.27289 (18)0.9115 (6)0.4382 (2)0.0403 (15)
H2WB0.24930.90650.43660.060*
H2WA0.28000.99230.43370.060*
C10.1391 (3)0.2616 (10)0.2546 (4)0.043 (2)
C20.1242 (3)0.2919 (11)0.2005 (4)0.0470 (19)
C30.0891 (3)0.2376 (13)0.1702 (4)0.060 (2)
H30.07330.18020.18360.072*
C40.0773 (3)0.2685 (13)0.1191 (4)0.062 (2)
H40.05350.23080.09890.074*
C50.0999 (4)0.3538 (13)0.0978 (4)0.063 (2)
C60.1349 (3)0.4046 (12)0.1290 (4)0.061 (2)
H60.15100.46070.11560.073*
C70.1469 (3)0.3760 (12)0.1792 (4)0.056 (2)
H70.17080.41360.19910.067*
C80.0869 (4)0.3882 (14)0.0420 (4)0.074 (3)
C90.0480 (6)0.3159 (19)0.0139 (6)0.122 (5)
H9A0.05150.21440.01550.183*
H9B0.04020.34590.02050.183*
H9C0.02770.34180.02890.183*
C100.1168 (5)0.3347 (18)0.0178 (5)0.106 (4)
H10A0.14040.39210.02820.159*
H10B0.10590.34010.01790.159*
H10C0.12340.23750.02750.159*
C110.0783 (6)0.5450 (18)0.0339 (6)0.126 (5)
H11A0.05750.57120.04810.190*
H11B0.07000.56510.00130.190*
H11C0.10180.59860.04980.190*
C120.1686 (3)0.0853 (9)0.3980 (3)0.0351 (18)
C130.1426 (3)0.0332 (10)0.4055 (4)0.0421 (18)
C140.1035 (3)0.0393 (11)0.3808 (4)0.050 (2)
H140.09190.03300.35860.061*
C150.0802 (3)0.1527 (11)0.3882 (5)0.059 (2)
H150.05310.15320.37140.071*
C160.0961 (3)0.2624 (11)0.4195 (5)0.059 (2)
C170.1353 (3)0.2543 (11)0.4440 (4)0.058 (2)
H170.14690.32710.46600.070*
C180.1589 (3)0.1440 (10)0.4377 (4)0.0496 (19)
H180.18580.14340.45520.059*
C190.0713 (4)0.3889 (13)0.4291 (6)0.074 (3)
C200.0774 (5)0.4049 (16)0.4861 (6)0.104 (4)
H20A0.06060.33850.49640.156*
H20B0.10470.38570.50400.156*
H20C0.07080.50020.49320.156*
C210.0857 (4)0.5243 (13)0.4113 (6)0.082 (3)
H21A0.07110.60370.41850.123*
H21B0.11350.53670.42810.123*
H21C0.08160.51880.37580.123*
C220.0286 (4)0.3700 (16)0.4035 (7)0.110 (4)
H22A0.02460.35650.36830.165*
H22B0.01890.28810.41690.165*
H22C0.01430.45310.40850.165*
C230.3064 (3)0.2987 (9)0.4273 (3)0.0357 (18)
C240.3482 (3)0.2792 (11)0.4589 (4)0.0464 (19)
C250.3606 (3)0.1495 (11)0.4818 (4)0.055 (2)
H250.34300.07330.47570.066*
C260.3988 (3)0.1308 (13)0.5135 (5)0.069 (2)
H260.40620.04210.52810.083*
C270.4254 (4)0.2384 (15)0.5237 (6)0.087 (3)
C280.4133 (4)0.3679 (14)0.4968 (5)0.081 (3)
H280.43160.44170.50080.097*
C290.3758 (3)0.3872 (12)0.4654 (5)0.066 (2)
H290.36890.47300.44840.079*
C300.4666 (5)0.221 (2)0.5597 (8)0.131 (5)
C310.4754 (6)0.073 (2)0.5814 (9)0.184 (8)
H31A0.47490.00680.55510.276*
H31B0.45570.04670.59730.276*
H31C0.50120.07220.60560.276*
C320.4994 (6)0.277 (3)0.5377 (9)0.182 (7)
H32A0.50510.20660.51590.273*
H32B0.52300.29710.56440.273*
H32C0.49030.36290.51910.273*
C330.4684 (6)0.311 (2)0.6046 (8)0.174 (6)
H33A0.49110.28360.63180.260*
H33B0.44470.29730.61430.260*
H33C0.47070.40930.59660.260*
C340.2270 (3)0.5196 (9)0.4683 (3)0.0361 (19)
C350.2207 (3)0.5395 (9)0.5185 (3)0.0392 (17)
C360.1985 (3)0.4442 (10)0.5365 (3)0.0442 (19)
H360.18730.36500.51770.053*
C370.1929 (3)0.4672 (10)0.5829 (4)0.050 (2)
H370.17730.40340.59430.060*
C380.2097 (3)0.5814 (11)0.6131 (4)0.0542 (19)
C390.2324 (3)0.6772 (11)0.5932 (4)0.053 (2)
H390.24400.75640.61180.064*
C400.2375 (3)0.6553 (10)0.5474 (4)0.0454 (18)
H400.25250.71970.53530.055*
C410.2040 (4)0.6068 (13)0.6639 (5)0.075 (3)
C420.1835 (5)0.4932 (14)0.6816 (5)0.089 (4)
H42A0.18420.51170.71570.134*
H42B0.19640.40400.67980.134*
H42C0.15640.48880.66110.134*
C430.2483 (5)0.5993 (17)0.7042 (5)0.106 (4)
H43A0.24660.62210.73700.160*
H43B0.26550.66640.69490.160*
H43C0.25890.50490.70440.160*
C440.1931 (5)0.7564 (15)0.6704 (5)0.091 (4)
H44A0.16650.77440.64970.136*
H44B0.21120.81940.66090.136*
H44C0.19460.77260.70480.136*
C450.1919 (2)0.6687 (8)0.3352 (3)0.0300 (17)
C460.1501 (3)0.6823 (9)0.3038 (3)0.0374 (17)
C470.1234 (3)0.5714 (10)0.3011 (4)0.0440 (19)
H470.13120.49090.32100.053*
C480.0850 (3)0.5809 (11)0.2685 (4)0.056 (2)
H480.06740.50570.26670.067*
C490.0726 (3)0.6994 (12)0.2390 (5)0.067 (2)
C500.0997 (3)0.8112 (11)0.2450 (4)0.056 (2)
H500.09180.89400.22640.068*
C510.1369 (3)0.8038 (10)0.2767 (4)0.0462 (19)
H510.15380.88190.28030.055*
C520.0328 (4)0.7049 (17)0.1989 (7)0.098 (4)
C530.0203 (5)0.571 (2)0.1728 (7)0.146 (5)
H53A0.00110.59000.14110.219*
H53B0.00860.51150.19250.219*
H53C0.04290.52420.16750.219*
C540.0009 (6)0.724 (2)0.2283 (8)0.159 (6)
H54A0.01160.68950.26180.239*
H54B0.02270.67200.21170.239*
H54C0.00550.82360.22920.239*
C550.0282 (6)0.810 (2)0.1620 (8)0.166 (6)
H55A0.00730.78240.13280.249*
H55B0.05260.81990.15350.249*
H55C0.02150.89880.17440.249*
C560.2719 (3)0.4525 (9)0.2959 (3)0.0339 (19)
C570.2782 (3)0.4395 (9)0.2452 (3)0.0427 (18)
C580.2626 (3)0.3265 (10)0.2135 (4)0.054 (2)
H580.24760.25810.22390.065*
C590.2685 (4)0.3127 (11)0.1679 (4)0.059 (2)
H590.25740.23540.14780.071*
C600.2909 (4)0.4128 (11)0.1505 (4)0.060 (2)
C610.3061 (3)0.5266 (11)0.1818 (4)0.055 (2)
H610.32060.59640.17110.066*
C620.3005 (3)0.5396 (10)0.2288 (4)0.049 (2)
H620.31160.61590.24930.059*
C630.2979 (5)0.3977 (14)0.0998 (5)0.086 (3)
C640.3155 (5)0.5161 (16)0.0826 (5)0.109 (4)
H64A0.34170.53190.10480.164*
H64B0.29960.59950.08180.164*
H64C0.31720.49680.04960.164*
C650.3074 (5)0.2502 (16)0.0890 (6)0.103 (4)
H65A0.30930.24480.05540.155*
H65B0.28680.18740.09230.155*
H65C0.33230.22240.11210.155*
C660.2514 (6)0.4129 (18)0.0581 (6)0.125 (5)
H66A0.24110.50650.06050.188*
H66B0.23410.34310.06580.188*
H66C0.25280.39760.02480.188*
C670.3302 (3)0.8839 (10)0.3644 (3)0.0388 (19)
C680.3551 (3)1.0026 (10)0.3575 (4)0.0465 (19)
C690.3387 (3)1.1192 (11)0.3268 (5)0.060 (2)
H690.31151.11990.31050.072*
C700.3617 (3)1.2337 (12)0.3200 (5)0.069 (2)
H700.34991.30740.29840.082*
C710.4014 (3)1.2384 (12)0.3448 (5)0.069 (2)
C720.4180 (3)1.1232 (12)0.3761 (5)0.066 (2)
H720.44491.12340.39330.080*
C730.3948 (3)1.0103 (12)0.3817 (4)0.058 (2)
H730.40660.93600.40280.070*
C740.4260 (4)1.3648 (14)0.3378 (7)0.089 (3)
C750.4082 (4)1.5011 (14)0.3530 (7)0.105 (4)
H75A0.41221.50070.38840.158*
H75B0.38021.50470.33580.158*
H75C0.42101.58290.34400.158*
C760.4206 (5)1.3788 (18)0.2805 (7)0.120 (4)
H76A0.43321.46470.27430.180*
H76B0.39281.38200.26270.180*
H76C0.43251.29820.26940.180*
C770.4685 (5)1.3515 (18)0.3629 (8)0.133 (5)
H77A0.47291.34300.39840.199*
H77B0.48201.43440.35610.199*
H77C0.47861.26820.35080.199*
C780.3618 (3)0.7088 (12)0.5065 (4)0.053 (2)
C790.3773 (4)0.6840 (13)0.5612 (4)0.062 (2)
C800.4139 (4)0.7294 (15)0.5894 (4)0.074 (3)
H800.43050.77530.57390.089*
C810.4269 (4)0.7086 (15)0.6408 (5)0.079 (3)
H810.45190.73990.65940.095*
C820.4022 (4)0.6406 (16)0.6645 (5)0.084 (3)
C830.3659 (4)0.5960 (14)0.6357 (4)0.073 (3)
H830.34940.54880.65120.087*
C840.3525 (4)0.6175 (14)0.5850 (4)0.069 (2)
H840.32720.58800.56680.083*
C850.4149 (6)0.616 (2)0.7213 (5)0.110 (4)
C860.3854 (6)0.662 (2)0.7440 (7)0.153 (5)
H86A0.39650.66220.77970.230*
H86B0.36310.59840.73470.230*
H86C0.37680.75670.73280.230*
C870.4299 (7)0.472 (2)0.7335 (7)0.170 (6)
H87A0.45840.47310.74230.255*
H87B0.41950.41170.70500.255*
H87C0.42170.43730.76120.255*
C880.4479 (7)0.712 (2)0.7468 (7)0.164 (6)
H88A0.44270.80580.73280.245*
H88B0.47220.67670.74230.245*
H88C0.45020.71530.78190.245*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pr10.0312 (3)0.0197 (2)0.0273 (3)0.00240 (18)0.00606 (19)0.00266 (17)
Pr20.0339 (3)0.0216 (2)0.0278 (3)0.00361 (18)0.0075 (2)0.00178 (18)
O10.039 (4)0.049 (4)0.037 (4)0.001 (3)0.001 (3)0.011 (3)
O20.049 (4)0.068 (5)0.045 (4)0.018 (4)0.008 (3)0.014 (4)
O30.038 (4)0.044 (4)0.040 (4)0.007 (3)0.005 (3)0.011 (3)
O40.035 (4)0.034 (3)0.038 (3)0.003 (3)0.008 (3)0.012 (3)
O50.036 (3)0.025 (3)0.048 (4)0.005 (3)0.003 (3)0.007 (3)
O60.044 (4)0.030 (3)0.043 (4)0.006 (3)0.008 (3)0.005 (3)
O70.061 (4)0.033 (3)0.037 (4)0.011 (3)0.021 (3)0.005 (3)
O80.055 (4)0.035 (3)0.040 (4)0.011 (3)0.021 (3)0.000 (3)
O90.043 (3)0.023 (3)0.030 (3)0.006 (3)0.000 (3)0.006 (2)
O100.033 (3)0.027 (3)0.046 (4)0.005 (3)0.001 (3)0.006 (3)
O110.054 (4)0.027 (3)0.042 (4)0.005 (3)0.026 (3)0.001 (3)
O120.074 (5)0.039 (4)0.041 (4)0.010 (3)0.027 (4)0.008 (3)
O130.032 (4)0.033 (3)0.047 (4)0.004 (3)0.010 (3)0.002 (3)
O140.037 (4)0.050 (4)0.050 (4)0.007 (3)0.008 (3)0.023 (3)
O150.053 (4)0.050 (4)0.039 (4)0.003 (3)0.003 (3)0.004 (3)
O160.058 (5)0.092 (6)0.050 (5)0.016 (4)0.003 (4)0.019 (4)
O1W0.063 (4)0.019 (3)0.034 (3)0.004 (3)0.017 (3)0.005 (2)
O2W0.052 (4)0.020 (3)0.047 (4)0.002 (3)0.010 (3)0.008 (3)
C10.049 (5)0.033 (4)0.043 (5)0.004 (4)0.007 (4)0.004 (4)
C20.047 (4)0.048 (4)0.041 (4)0.003 (3)0.006 (3)0.008 (3)
C30.056 (4)0.066 (5)0.049 (4)0.003 (4)0.001 (4)0.006 (4)
C40.059 (5)0.068 (5)0.049 (4)0.001 (4)0.002 (4)0.005 (4)
C50.070 (4)0.066 (4)0.046 (4)0.009 (4)0.006 (4)0.006 (4)
C60.065 (5)0.062 (5)0.050 (4)0.007 (4)0.007 (4)0.008 (4)
C70.057 (4)0.057 (4)0.048 (4)0.003 (4)0.007 (4)0.008 (4)
C80.096 (7)0.079 (6)0.039 (5)0.027 (6)0.008 (5)0.011 (5)
C90.145 (10)0.135 (10)0.064 (8)0.019 (9)0.003 (8)0.020 (8)
C100.122 (9)0.130 (10)0.062 (7)0.023 (8)0.021 (7)0.021 (7)
C110.176 (11)0.110 (9)0.072 (8)0.031 (9)0.003 (8)0.004 (8)
C120.035 (4)0.037 (4)0.036 (4)0.001 (3)0.015 (3)0.008 (3)
C130.036 (4)0.040 (4)0.052 (4)0.004 (3)0.016 (3)0.006 (3)
C140.038 (4)0.046 (4)0.063 (4)0.004 (3)0.008 (3)0.014 (4)
C150.044 (4)0.054 (4)0.076 (5)0.013 (4)0.010 (4)0.008 (4)
C160.045 (4)0.043 (4)0.089 (5)0.013 (3)0.022 (4)0.008 (4)
C170.047 (4)0.043 (4)0.081 (5)0.007 (4)0.014 (4)0.018 (4)
C180.038 (4)0.041 (4)0.068 (4)0.004 (3)0.014 (3)0.015 (4)
C190.056 (5)0.050 (5)0.123 (7)0.016 (5)0.038 (5)0.002 (6)
C200.108 (8)0.076 (8)0.141 (10)0.031 (7)0.057 (8)0.003 (8)
C210.084 (7)0.052 (6)0.115 (8)0.020 (6)0.038 (6)0.001 (6)
C220.082 (7)0.075 (7)0.168 (10)0.030 (6)0.032 (7)0.012 (8)
C230.032 (4)0.035 (4)0.043 (4)0.003 (3)0.015 (4)0.007 (4)
C240.035 (4)0.042 (4)0.058 (4)0.002 (3)0.008 (3)0.001 (4)
C250.038 (4)0.053 (4)0.066 (4)0.001 (3)0.002 (4)0.007 (4)
C260.046 (4)0.065 (5)0.081 (5)0.006 (4)0.006 (4)0.009 (4)
C270.055 (4)0.073 (5)0.105 (5)0.005 (4)0.018 (4)0.003 (5)
C280.052 (5)0.068 (5)0.101 (5)0.004 (4)0.012 (4)0.002 (5)
C290.040 (4)0.054 (4)0.088 (5)0.000 (4)0.004 (4)0.001 (4)
C300.079 (7)0.108 (8)0.160 (9)0.002 (7)0.034 (7)0.009 (8)
C310.117 (11)0.141 (13)0.218 (14)0.019 (11)0.069 (11)0.005 (12)
C320.104 (12)0.189 (14)0.210 (14)0.008 (12)0.019 (12)0.002 (13)
C330.117 (10)0.158 (11)0.186 (11)0.003 (9)0.049 (9)0.007 (10)
C340.049 (5)0.029 (4)0.030 (4)0.001 (4)0.010 (4)0.004 (3)
C350.056 (4)0.031 (3)0.034 (4)0.006 (3)0.018 (3)0.001 (3)
C360.060 (4)0.036 (4)0.041 (4)0.010 (3)0.022 (4)0.004 (3)
C370.071 (5)0.042 (4)0.043 (4)0.008 (4)0.028 (4)0.002 (3)
C380.085 (4)0.041 (4)0.044 (4)0.006 (4)0.030 (4)0.003 (3)
C390.077 (5)0.045 (4)0.042 (4)0.011 (4)0.022 (4)0.002 (3)
C400.064 (4)0.036 (4)0.039 (4)0.009 (3)0.020 (3)0.001 (3)
C410.129 (7)0.054 (5)0.055 (5)0.011 (6)0.048 (5)0.006 (5)
C420.147 (9)0.076 (7)0.066 (7)0.009 (7)0.063 (7)0.004 (6)
C430.161 (10)0.087 (8)0.069 (8)0.012 (8)0.032 (8)0.004 (7)
C440.145 (9)0.072 (7)0.074 (7)0.011 (7)0.061 (7)0.004 (6)
C450.032 (4)0.028 (4)0.029 (4)0.003 (3)0.007 (3)0.007 (3)
C460.035 (4)0.032 (3)0.040 (4)0.004 (3)0.003 (3)0.002 (3)
C470.039 (4)0.032 (4)0.055 (4)0.004 (3)0.005 (3)0.003 (3)
C480.043 (4)0.041 (4)0.073 (5)0.006 (4)0.003 (4)0.000 (4)
C490.045 (4)0.058 (4)0.082 (5)0.002 (4)0.007 (4)0.000 (4)
C500.048 (4)0.042 (4)0.066 (5)0.003 (4)0.003 (4)0.009 (4)
C510.043 (4)0.034 (4)0.052 (4)0.003 (3)0.001 (3)0.009 (3)
C520.050 (6)0.090 (7)0.123 (8)0.012 (6)0.022 (6)0.002 (6)
C530.100 (9)0.129 (10)0.153 (10)0.000 (8)0.051 (8)0.003 (9)
C540.099 (9)0.165 (10)0.169 (11)0.021 (9)0.031 (9)0.019 (9)
C550.110 (9)0.150 (10)0.175 (11)0.018 (9)0.058 (9)0.023 (9)
C560.049 (5)0.030 (4)0.030 (4)0.000 (4)0.023 (4)0.004 (4)
C570.066 (4)0.032 (3)0.037 (4)0.006 (3)0.027 (3)0.001 (3)
C580.082 (5)0.042 (4)0.045 (4)0.015 (4)0.029 (4)0.005 (3)
C590.092 (5)0.045 (4)0.045 (4)0.014 (4)0.030 (4)0.002 (4)
C600.099 (5)0.045 (4)0.048 (4)0.010 (4)0.038 (4)0.002 (3)
C610.084 (5)0.044 (4)0.047 (4)0.011 (4)0.034 (4)0.004 (4)
C620.079 (5)0.035 (4)0.042 (4)0.009 (4)0.031 (4)0.000 (3)
C630.150 (8)0.056 (6)0.068 (6)0.009 (6)0.056 (6)0.002 (5)
C640.186 (12)0.091 (9)0.077 (8)0.013 (9)0.080 (8)0.011 (7)
C650.172 (10)0.071 (7)0.087 (8)0.005 (8)0.068 (7)0.003 (7)
C660.199 (12)0.095 (9)0.080 (8)0.011 (9)0.039 (9)0.007 (8)
C670.044 (5)0.036 (4)0.040 (4)0.002 (4)0.018 (4)0.002 (4)
C680.035 (4)0.041 (4)0.066 (4)0.006 (3)0.019 (3)0.008 (4)
C690.042 (4)0.046 (4)0.091 (5)0.004 (4)0.017 (4)0.009 (4)
C700.049 (4)0.048 (4)0.108 (5)0.007 (4)0.021 (4)0.016 (4)
C710.050 (4)0.049 (4)0.110 (5)0.012 (4)0.024 (4)0.008 (4)
C720.043 (4)0.057 (4)0.096 (5)0.013 (4)0.015 (4)0.008 (4)
C730.044 (4)0.051 (4)0.078 (5)0.006 (3)0.015 (4)0.010 (4)
C740.064 (5)0.059 (5)0.141 (7)0.009 (5)0.027 (5)0.010 (6)
C750.091 (8)0.062 (7)0.168 (10)0.016 (6)0.045 (7)0.009 (7)
C760.099 (8)0.088 (8)0.180 (10)0.024 (7)0.052 (8)0.018 (8)
C770.084 (8)0.096 (9)0.214 (12)0.025 (8)0.036 (9)0.012 (9)
C780.053 (5)0.056 (5)0.045 (5)0.003 (4)0.008 (4)0.006 (4)
C790.063 (5)0.074 (5)0.041 (4)0.001 (4)0.003 (4)0.006 (4)
C800.072 (5)0.090 (5)0.050 (4)0.005 (5)0.002 (4)0.011 (4)
C810.079 (5)0.096 (5)0.050 (5)0.001 (5)0.002 (4)0.007 (5)
C820.096 (5)0.100 (5)0.048 (4)0.012 (5)0.006 (4)0.009 (4)
C830.079 (5)0.086 (5)0.046 (4)0.002 (5)0.009 (4)0.013 (4)
C840.073 (5)0.078 (5)0.050 (4)0.003 (4)0.006 (4)0.010 (4)
C850.132 (8)0.125 (8)0.053 (6)0.036 (7)0.002 (6)0.000 (6)
C860.172 (11)0.188 (11)0.082 (9)0.027 (10)0.011 (9)0.008 (9)
C870.212 (11)0.171 (11)0.088 (9)0.043 (10)0.016 (9)0.006 (9)
C880.188 (11)0.180 (11)0.089 (9)0.006 (10)0.012 (9)0.006 (9)
Geometric parameters (Å, º) top
Pr1—O112.395 (6)C36—H360.9300
Pr1—O92.422 (5)C37—C381.383 (14)
Pr1—O72.423 (6)C37—H370.9300
Pr1—O52.469 (6)C38—C391.421 (14)
Pr1—O1W2.539 (5)C38—C411.511 (14)
Pr1—O32.552 (6)C39—C401.358 (13)
Pr1—O12.555 (6)C39—H390.9300
Pr1—O42.593 (5)C40—H400.9300
Pr1—O62.807 (6)C41—C421.453 (16)
Pr2—O82.366 (6)C41—C441.482 (17)
Pr2—O122.375 (6)C41—C431.64 (2)
Pr2—O62.447 (6)C42—H42A0.9600
Pr2—O102.490 (6)C42—H42B0.9600
Pr2—O142.557 (6)C42—H42C0.9600
Pr2—O152.562 (7)C43—H43A0.9600
Pr2—O2W2.567 (5)C43—H43B0.9600
Pr2—O132.589 (6)C43—H43C0.9600
Pr2—O92.775 (6)C44—H44A0.9600
O1—C11.199 (11)C44—H44B0.9600
O2—C11.340 (11)C44—H44C0.9600
O2—H20.8200C45—C461.481 (12)
O3—C121.273 (10)C46—C511.371 (12)
O4—C121.251 (10)C46—C471.389 (12)
O5—C231.253 (10)C47—C481.394 (13)
O6—C231.267 (10)C47—H470.9300
O7—C341.249 (10)C48—C491.377 (15)
O8—C341.270 (10)C48—H480.9300
O9—C451.276 (9)C49—C501.395 (15)
O10—C451.262 (10)C49—C521.516 (16)
O11—C561.258 (10)C50—C511.352 (13)
O12—C561.256 (10)C50—H500.9300
O13—C671.243 (10)C51—H510.9300
O14—C671.273 (11)C52—C551.40 (2)
O15—C781.207 (12)C52—C531.45 (2)
O16—C781.303 (12)C52—C541.58 (3)
O16—H160.8200C53—H53A0.9600
O1W—H1WB0.8202C53—H53B0.9600
O1W—H1WA0.8244C53—H53C0.9600
O2W—H2WB0.8200C54—H54A0.9600
O2W—H2WA0.8200C54—H54B0.9600
C1—C21.474 (13)C54—H54C0.9600
C2—C31.374 (14)C55—H55A0.9600
C2—C71.379 (14)C55—H55B0.9600
C3—C41.395 (15)C55—H55C0.9600
C3—H30.9300C56—C571.502 (11)
C4—C51.382 (16)C57—C621.384 (12)
C4—H40.9300C57—C581.388 (13)
C5—C61.368 (15)C58—C591.357 (14)
C5—C81.524 (15)C58—H580.9300
C6—C71.369 (14)C59—C601.405 (14)
C6—H60.9300C59—H590.9300
C7—H70.9300C60—C611.386 (14)
C8—C101.496 (19)C60—C631.513 (15)
C8—C111.51 (2)C61—C621.391 (13)
C8—C91.53 (2)C61—H610.9300
C9—H9A0.9600C62—H620.9300
C9—H9B0.9600C63—C641.423 (18)
C9—H9C0.9600C63—C651.477 (19)
C10—H10A0.9600C63—C661.71 (2)
C10—H10B0.9600C64—H64A0.9600
C10—H10C0.9600C64—H64B0.9600
C11—H11A0.9600C64—H64C0.9600
C11—H11B0.9600C65—H65A0.9600
C11—H11C0.9600C65—H65B0.9600
C12—C131.494 (12)C65—H65C0.9600
C13—C141.346 (13)C66—H66A0.9600
C13—C181.385 (13)C66—H66B0.9600
C14—C151.397 (13)C66—H66C0.9600
C14—H140.9300C67—C681.463 (12)
C15—C161.361 (15)C68—C731.364 (13)
C15—H150.9300C68—C691.406 (14)
C16—C171.353 (14)C69—C701.391 (14)
C16—C191.541 (14)C69—H690.9300
C17—C181.368 (13)C70—C711.368 (15)
C17—H170.9300C70—H700.9300
C18—H180.9300C71—C721.406 (17)
C19—C221.474 (18)C71—C741.514 (16)
C19—C211.505 (17)C72—C731.374 (14)
C19—C201.55 (2)C72—H720.9300
C20—H20A0.9600C73—H730.9300
C20—H20B0.9600C74—C771.46 (2)
C20—H20C0.9600C74—C751.537 (19)
C21—H21A0.9600C74—C761.56 (2)
C21—H21B0.9600C75—H75A0.9600
C21—H21C0.9600C75—H75B0.9600
C22—H22A0.9600C75—H75C0.9600
C22—H22B0.9600C76—H76A0.9600
C22—H22C0.9600C76—H76B0.9600
C23—C241.490 (13)C76—H76C0.9600
C24—C291.378 (14)C77—H77A0.9600
C24—C251.385 (14)C77—H77B0.9600
C25—C261.385 (14)C77—H77C0.9600
C25—H250.9300C78—C791.483 (15)
C26—C271.349 (17)C79—C801.367 (16)
C26—H260.9300C79—C841.390 (16)
C27—C281.428 (18)C80—C811.387 (16)
C27—C301.513 (19)C80—H800.9300
C28—C291.366 (15)C81—C821.392 (19)
C28—H280.9300C81—H810.9300
C29—H290.9300C82—C831.359 (18)
C30—C331.50 (3)C82—C851.536 (19)
C30—C311.51 (3)C83—C841.372 (15)
C30—C321.55 (3)C83—H830.9300
C31—H31A0.9600C84—H840.9300
C31—H31B0.9600C85—C861.43 (2)
C31—H31C0.9600C85—C871.45 (2)
C32—H32A0.9600C85—C881.47 (3)
C32—H32B0.9600C86—H86A0.9600
C32—H32C0.9600C86—H86B0.9600
C33—H33A0.9600C86—H86C0.9600
C33—H33B0.9600C87—H87A0.9600
C33—H33C0.9600C87—H87B0.9600
C34—C351.493 (12)C87—H87C0.9600
C35—C361.378 (12)C88—H88A0.9600
C35—C401.379 (12)C88—H88B0.9600
C36—C371.384 (12)C88—H88C0.9600
O11—Pr1—O976.46 (19)H33A—C33—H33B109.5
O11—Pr1—O7134.2 (2)C30—C33—H33C109.5
O9—Pr1—O773.9 (2)H33A—C33—H33C109.5
O11—Pr1—O581.8 (2)H33B—C33—H33C109.5
O9—Pr1—O5126.08 (18)O7—C34—O8124.7 (8)
O7—Pr1—O588.2 (2)O7—C34—C35118.9 (8)
O11—Pr1—O1W74.35 (19)O8—C34—C35116.4 (8)
O9—Pr1—O1W140.98 (18)C36—C35—C40119.1 (9)
O7—Pr1—O1W144.63 (19)C36—C35—C34121.2 (8)
O5—Pr1—O1W74.31 (19)C40—C35—C34119.6 (8)
O11—Pr1—O3137.4 (2)C35—C36—C37119.6 (9)
O9—Pr1—O3106.4 (2)C35—C36—H36120.2
O7—Pr1—O384.8 (2)C37—C36—H36120.2
O5—Pr1—O3122.45 (19)C38—C37—C36122.6 (9)
O1W—Pr1—O379.5 (2)C38—C37—H37118.7
O11—Pr1—O171.5 (2)C36—C37—H37118.7
O9—Pr1—O174.66 (19)C37—C38—C39116.1 (9)
O7—Pr1—O1130.5 (2)C37—C38—C41123.0 (10)
O5—Pr1—O1141.4 (2)C39—C38—C41120.9 (10)
O1W—Pr1—O171.90 (19)C40—C39—C38121.1 (10)
O3—Pr1—O168.7 (2)C40—C39—H39119.4
O11—Pr1—O4140.54 (19)C38—C39—H39119.4
O9—Pr1—O4143.00 (19)C39—C40—C35121.4 (9)
O7—Pr1—O475.41 (19)C39—C40—H40119.3
O5—Pr1—O472.59 (18)C35—C40—H40119.3
O1W—Pr1—O470.14 (19)C42—C41—C44118.8 (12)
O3—Pr1—O450.37 (18)C42—C41—C38114.9 (10)
O1—Pr1—O4111.84 (19)C44—C41—C38112.1 (10)
O11—Pr1—O667.6 (2)C42—C41—C43101.6 (11)
O9—Pr1—O677.36 (18)C44—C41—C43100.6 (11)
O7—Pr1—O672.25 (19)C38—C41—C43106.2 (11)
O5—Pr1—O648.72 (17)C41—C42—H42A109.5
O1W—Pr1—O6113.67 (19)C41—C42—H42B109.5
O3—Pr1—O6154.96 (19)H42A—C42—H42B109.5
O1—Pr1—O6134.61 (19)C41—C42—H42C109.5
O4—Pr1—O6112.09 (18)H42A—C42—H42C109.5
O8—Pr2—O12133.2 (2)H42B—C42—H42C109.5
O8—Pr2—O676.8 (2)C41—C43—H43A109.5
O12—Pr2—O674.1 (2)C41—C43—H43B109.5
O8—Pr2—O1081.6 (2)H43A—C43—H43B109.5
O12—Pr2—O1087.1 (2)C41—C43—H43C109.5
O6—Pr2—O10126.53 (19)H43A—C43—H43C109.5
O8—Pr2—O14139.7 (2)H43B—C43—H43C109.5
O12—Pr2—O1483.3 (2)C41—C44—H44A109.5
O6—Pr2—O14104.5 (2)C41—C44—H44B109.5
O10—Pr2—O14122.78 (19)H44A—C44—H44B109.5
O8—Pr2—O1573.1 (2)C41—C44—H44C109.5
O12—Pr2—O15130.7 (2)H44A—C44—H44C109.5
O6—Pr2—O1574.7 (2)H44B—C44—H44C109.5
O10—Pr2—O15142.2 (2)O10—C45—O9119.8 (7)
O14—Pr2—O1568.7 (2)O10—C45—C46120.2 (7)
O8—Pr2—O2W74.0 (2)O9—C45—C46119.9 (7)
O12—Pr2—O2W145.0 (2)C51—C46—C47118.7 (9)
O6—Pr2—O2W140.5 (2)C51—C46—C45121.0 (8)
O10—Pr2—O2W74.60 (19)C47—C46—C45120.4 (8)
O14—Pr2—O2W82.1 (2)C46—C47—C48119.8 (9)
O15—Pr2—O2W71.6 (2)C46—C47—H47120.1
O8—Pr2—O13140.8 (2)C48—C47—H47120.1
O12—Pr2—O1375.5 (2)C49—C48—C47121.4 (10)
O6—Pr2—O13142.4 (2)C49—C48—H48119.3
O10—Pr2—O1372.94 (18)C47—C48—H48119.3
O14—Pr2—O1350.02 (19)C48—C49—C50116.7 (10)
O15—Pr2—O13110.5 (2)C48—C49—C52122.2 (11)
O2W—Pr2—O1370.80 (19)C50—C49—C52120.9 (12)
O8—Pr2—O967.07 (19)C51—C50—C49122.5 (10)
O12—Pr2—O971.4 (2)C51—C50—H50118.8
O6—Pr2—O977.60 (18)C49—C50—H50118.8
O10—Pr2—O948.93 (17)C50—C51—C46120.7 (9)
O14—Pr2—O9153.19 (19)C50—C51—H51119.6
O15—Pr2—O9135.53 (19)C46—C51—H51119.6
O2W—Pr2—O9113.65 (18)C55—C52—C53106.5 (17)
O13—Pr2—O9112.71 (17)C55—C52—C49116.8 (14)
C1—O1—Pr1144.7 (6)C53—C52—C49114.8 (12)
C1—O2—H2109.5C55—C52—C54110.7 (16)
C12—O3—Pr195.1 (5)C53—C52—C54101.8 (15)
C12—O4—Pr193.7 (5)C49—C52—C54105.1 (14)
C23—O5—Pr1103.1 (5)C52—C53—H53A109.5
C23—O6—Pr2171.6 (6)C52—C53—H53B109.5
C23—O6—Pr186.6 (5)H53A—C53—H53B109.5
Pr2—O6—Pr1101.7 (2)C52—C53—H53C109.5
C34—O7—Pr1137.1 (6)H53A—C53—H53C109.5
C34—O8—Pr2141.2 (6)H53B—C53—H53C109.5
C45—O9—Pr1168.0 (5)C52—C54—H54A109.5
C45—O9—Pr288.7 (5)C52—C54—H54B109.5
Pr1—O9—Pr2103.32 (19)H54A—C54—H54B109.5
C45—O10—Pr2102.6 (5)C52—C54—H54C109.5
C56—O11—Pr1138.4 (5)H54A—C54—H54C109.5
C56—O12—Pr2138.5 (6)H54B—C54—H54C109.5
C67—O13—Pr294.3 (5)C52—C55—H55A109.5
C67—O14—Pr295.0 (5)C52—C55—H55B109.5
C78—O15—Pr2143.7 (7)H55A—C55—H55B109.5
C78—O16—H16109.5C52—C55—H55C109.5
Pr1—O1W—H1WB149.7H55A—C55—H55C109.5
Pr1—O1W—H1WA94.8H55B—C55—H55C109.5
H1WB—O1W—H1WA113.3O12—C56—O11126.6 (8)
Pr2—O2W—H2WB98.5O12—C56—C57117.5 (7)
Pr2—O2W—H2WA130.9O11—C56—C57115.9 (8)
H2WB—O2W—H2WA113.3C62—C57—C58117.6 (9)
O1—C1—O2122.6 (9)C62—C57—C56120.8 (8)
O1—C1—C2123.0 (9)C58—C57—C56121.5 (8)
O2—C1—C2114.4 (9)C59—C58—C57122.1 (9)
C3—C2—C7118.4 (10)C59—C58—H58119.0
C3—C2—C1123.2 (9)C57—C58—H58119.0
C7—C2—C1118.4 (9)C58—C59—C60121.3 (10)
C2—C3—C4120.0 (11)C58—C59—H59119.3
C2—C3—H3120.0C60—C59—H59119.3
C4—C3—H3120.0C61—C60—C59116.6 (9)
C5—C4—C3121.6 (11)C61—C60—C63121.7 (10)
C5—C4—H4119.2C59—C60—C63121.7 (10)
C3—C4—H4119.2C60—C61—C62121.9 (9)
C6—C5—C4116.9 (11)C60—C61—H61119.0
C6—C5—C8121.4 (12)C62—C61—H61119.0
C4—C5—C8121.7 (11)C57—C62—C61120.4 (9)
C5—C6—C7122.3 (11)C57—C62—H62119.8
C5—C6—H6118.8C61—C62—H62119.8
C7—C6—H6118.8C64—C63—C65121.1 (13)
C6—C7—C2120.8 (11)C64—C63—C60116.7 (11)
C6—C7—H7119.6C65—C63—C60112.8 (11)
C2—C7—H7119.6C64—C63—C6697.5 (12)
C10—C8—C11113.5 (14)C65—C63—C6699.6 (12)
C10—C8—C5110.7 (11)C60—C63—C66104.1 (11)
C11—C8—C5110.3 (11)C63—C64—H64A109.5
C10—C8—C9105.2 (13)C63—C64—H64B109.5
C11—C8—C9104.2 (12)H64A—C64—H64B109.5
C5—C8—C9112.8 (12)C63—C64—H64C109.5
C8—C9—H9A109.5H64A—C64—H64C109.5
C8—C9—H9B109.5H64B—C64—H64C109.5
H9A—C9—H9B109.5C63—C65—H65A109.5
C8—C9—H9C109.5C63—C65—H65B109.5
H9A—C9—H9C109.5H65A—C65—H65B109.5
H9B—C9—H9C109.5C63—C65—H65C109.5
C8—C10—H10A109.5H65A—C65—H65C109.5
C8—C10—H10B109.5H65B—C65—H65C109.5
H10A—C10—H10B109.5C63—C66—H66A109.5
C8—C10—H10C109.5C63—C66—H66B109.5
H10A—C10—H10C109.5H66A—C66—H66B109.5
H10B—C10—H10C109.5C63—C66—H66C109.5
C8—C11—H11A109.5H66A—C66—H66C109.5
C8—C11—H11B109.5H66B—C66—H66C109.5
H11A—C11—H11B109.5O13—C67—O14119.8 (8)
C8—C11—H11C109.5O13—C67—C68120.2 (8)
H11A—C11—H11C109.5O14—C67—C68120.0 (9)
H11B—C11—H11C109.5C73—C68—C69116.0 (9)
O4—C12—O3120.4 (8)C73—C68—C67122.7 (9)
O4—C12—C13120.9 (8)C69—C68—C67121.3 (9)
O3—C12—C13118.7 (8)C70—C69—C68122.4 (10)
C14—C13—C18117.8 (9)C70—C69—H69118.8
C14—C13—C12122.4 (9)C68—C69—H69118.8
C18—C13—C12119.8 (8)C71—C70—C69120.3 (11)
C13—C14—C15120.9 (10)C71—C70—H70119.8
C13—C14—H14119.6C69—C70—H70119.8
C15—C14—H14119.6C70—C71—C72117.7 (10)
C16—C15—C14121.6 (10)C70—C71—C74119.9 (12)
C16—C15—H15119.2C72—C71—C74122.4 (11)
C14—C15—H15119.2C73—C72—C71120.9 (11)
C17—C16—C15116.6 (10)C73—C72—H72119.6
C17—C16—C19120.2 (11)C71—C72—H72119.6
C15—C16—C19123.2 (10)C68—C73—C72122.7 (11)
C16—C17—C18123.1 (10)C68—C73—H73118.6
C16—C17—H17118.5C72—C73—H73118.6
C18—C17—H17118.5C77—C74—C71114.5 (13)
C17—C18—C13120.0 (10)C77—C74—C75112.5 (14)
C17—C18—H18120.0C71—C74—C75108.8 (11)
C13—C18—H18120.0C77—C74—C76107.4 (14)
C22—C19—C21109.6 (12)C71—C74—C76107.2 (12)
C22—C19—C16111.8 (11)C75—C74—C76106.0 (13)
C21—C19—C16109.3 (10)C74—C75—H75A109.5
C22—C19—C20108.9 (12)C74—C75—H75B109.5
C21—C19—C20107.4 (12)H75A—C75—H75B109.5
C16—C19—C20109.7 (11)C74—C75—H75C109.5
C19—C20—H20A109.5H75A—C75—H75C109.5
C19—C20—H20B109.5H75B—C75—H75C109.5
H20A—C20—H20B109.5C74—C76—H76A109.5
C19—C20—H20C109.5C74—C76—H76B109.5
H20A—C20—H20C109.5H76A—C76—H76B109.5
H20B—C20—H20C109.5C74—C76—H76C109.5
C19—C21—H21A109.5H76A—C76—H76C109.5
C19—C21—H21B109.5H76B—C76—H76C109.5
H21A—C21—H21B109.5C74—C77—H77A109.5
C19—C21—H21C109.5C74—C77—H77B109.5
H21A—C21—H21C109.5H77A—C77—H77B109.5
H21B—C21—H21C109.5C74—C77—H77C109.5
C19—C22—H22A109.5H77A—C77—H77C109.5
C19—C22—H22B109.5H77B—C77—H77C109.5
H22A—C22—H22B109.5O15—C78—O16123.6 (10)
C19—C22—H22C109.5O15—C78—C79122.0 (10)
H22A—C22—H22C109.5O16—C78—C79114.4 (10)
H22B—C22—H22C109.5C80—C79—C84118.7 (11)
O5—C23—O6121.5 (8)C80—C79—C78123.0 (11)
O5—C23—C24119.1 (8)C84—C79—C78118.2 (11)
O6—C23—C24119.3 (8)C79—C80—C81121.5 (13)
C29—C24—C25118.2 (9)C79—C80—H80119.3
C29—C24—C23121.5 (9)C81—C80—H80119.3
C25—C24—C23120.3 (9)C80—C81—C82119.7 (13)
C24—C25—C26121.4 (10)C80—C81—H81120.2
C24—C25—H25119.3C82—C81—H81120.2
C26—C25—H25119.3C83—C82—C81118.0 (12)
C27—C26—C25121.5 (12)C83—C82—C85120.3 (14)
C27—C26—H26119.3C81—C82—C85121.8 (14)
C25—C26—H26119.3C82—C83—C84123.0 (13)
C26—C27—C28116.4 (11)C82—C83—H83118.5
C26—C27—C30121.9 (14)C84—C83—H83118.5
C28—C27—C30121.6 (14)C83—C84—C79119.2 (12)
C29—C28—C27122.3 (12)C83—C84—H84120.4
C29—C28—H28118.9C79—C84—H84120.4
C27—C28—H28118.9C86—C85—C87116 (2)
C28—C29—C24119.8 (11)C86—C85—C88100.0 (17)
C28—C29—H29120.1C87—C85—C88105.8 (17)
C24—C29—H29120.1C86—C85—C82112.5 (15)
C33—C30—C31103 (2)C87—C85—C82110.9 (15)
C33—C30—C27106.9 (16)C88—C85—C82111.0 (17)
C31—C30—C27114.4 (15)C85—C86—H86A109.5
C33—C30—C32106.6 (17)C85—C86—H86B109.5
C31—C30—C32112.7 (19)H86A—C86—H86B109.5
C27—C30—C32112.3 (18)C85—C86—H86C109.5
C30—C31—H31A109.5H86A—C86—H86C109.5
C30—C31—H31B109.5H86B—C86—H86C109.5
H31A—C31—H31B109.5C85—C87—H87A109.5
C30—C31—H31C109.5C85—C87—H87B109.5
H31A—C31—H31C109.5H87A—C87—H87B109.5
H31B—C31—H31C109.5C85—C87—H87C109.5
C30—C32—H32A109.5H87A—C87—H87C109.5
C30—C32—H32B109.5H87B—C87—H87C109.5
H32A—C32—H32B109.5C85—C88—H88A109.5
C30—C32—H32C109.5C85—C88—H88B109.5
H32A—C32—H32C109.5H88A—C88—H88B109.5
H32B—C32—H32C109.5C85—C88—H88C109.5
C30—C33—H33A109.5H88A—C88—H88C109.5
C30—C33—H33B109.5H88B—C88—H88C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2W—H2WB···O4i0.822.252.824 (8)127
O2W—H2WA···O5i0.821.952.759 (8)167
O1W—H1WA···O13ii0.822.502.866 (8)108
O1W—H1WB···O10ii0.822.012.767 (8)154
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formula[Pr2(C11H13O2)6(C11H14O2)2(H2O)2]
Mr1737.58
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)35.194 (6), 9.3857 (18), 27.956 (5)
β (°) 107.073 (4)
V3)8827 (3)
Z4
Radiation typeMo Kα
µ (mm1)1.15
Crystal size (mm)0.24 × 0.09 × 0.05
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.769, 0.841
No. of measured, independent and
observed [I > 2σ(I)] reflections
44864, 15556, 10611
Rint0.073
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.206, 1.02
No. of reflections15556
No. of parameters999
No. of restraints1092
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.1044P)2 + 37.5508P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)5.46, 1.00

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2W—H2WB···O4i0.822.252.824 (8)126.8
O2W—H2WA···O5i0.821.952.759 (8)167.1
O1W—H1WA···O13ii0.822.502.866 (8)108.0
O1W—H1WB···O10ii0.822.012.767 (8)154.1
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
 

Acknowledgements

The authors acknowledge the Doctoral Foundation of Henan Polytechnic University (B2008–58 648265).

References

First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, X., Ju, Y. L. & Zhang, T. T. (2007). J. Coord. Chem. 60, 1527–1530.  Web of Science CSD CrossRef CAS Google Scholar
First citationRoh, S. G., Nah, M. K., Oh, J. B., Baek, N. S., Park, K. M. & Kim, H. K. (2005). Polyhedron, 24, 137–142.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSingh, U. P., Kumar, R. & Upreti, S. (2007). J. Mol. Struct. 831, 97–105.  Web of Science CSD CrossRef CAS Google Scholar
First citationXu, L. J., Li, Y. Q. & Li, X. (2009). J. Rare Earths, 27, 372–375.  CrossRef Google Scholar
First citationYang, T.-H., Chen, Q., Zhuang, W., Wang, Z. & Yue, B.-Y. (2009). Acta Cryst. E65, m1152–m1153.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYang, J., Li, J. & Wang, Q. (2010). Acta Cryst. E66, m183–m184.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 8| August 2011| Pages m1160-m1161
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