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Acta Cryst. (2009). E65, m1167-m1168    [ doi:10.1107/S1600536809035016 ]

Bis(2-fluorobenzoato-[kappa]2O,O')bis(1,10-phenanthroline-[kappa]2N,N')lead(II) dihydrate

B.-S. Zhang

Abstract top

In the title compound, [Pb(C7H4FO2)2(C12H8N2)2]·2H2O, the PbII atom is coordinated by four N atoms from two bidentate chelating 1,10-phenanthroline (phen) ligands and four O atoms from two 2-fluorobenzoate ligands in an irregular polyhedral coordination geometry. Two carboxylate O atoms and one F atom are each disordered over two sites with occupancy factors of 0.60 and 0.40. The dihedral angle between the two phen ligands is 89.9 (1)°. The mean interplanar distances are alternatively of 3.44 (3) and 3.45 (3) Å, indicating [pi]-[pi] stacking interactions between the neighboring phen ligands. In the crystal, O-H...O, O-H...F and C-H...O hydrogen bonds link the complex molecules and uncoordinated water molecules into a supramolecular network.

Comment top

The synthesis was originally directed to repeat the synthesis of [Pb(C7H4FO2)2(C12H8N2)2(H2O)0.5].2H2O, (I), (Ye & Zhang, 2009). The title compound was unintentionally obtained and structurally related to (I).

The title compound (Fig .1) shows a structure similar to (I) and to those of the complexes with halobenzoate ligands, X–C6H4COO-, where X is F, Cl, Br and I (Zhang, 2004, 2005, 2006a,b,c; Zhang et al., 2005). The asymmetric unit of the title compound consists of a [Pb(C7H4FO2)2(C12H8N2)2] complex molecule and two uncoordinated water molecules. The PbII atom is coordinated by four N atoms from two bidentate chelating phen ligands and four O atoms from two 2-fluorobenzoate ligands in an irregular polyhedral coordination geometry, with Pb—N bond lengths in the range of 2.566 (8) to 2.675 (9)Å and Pb—O bond lengths in the range of 2.670 (8) to 2.95 (3)Å (Table 1). The dihedral angle of the two phen ligands is 89.9 (1)°, as distinct from (I) (0.0 (2)°). The mean interplanar distances are alternatively of 3.44 (3) and 3.45 (3) Å, indicating π–π stacking interactions between the neighboring phen ligands (Fig. 2). O—H···O, O—H···F and C—H···O hydrogen bonds are present (Table 2 ). A combination of the π–π stacking interactions and hydrogen bonds leads to a supramolecular network.

Related literature top

For other complexes with a 2(or 4)-fluorobenzoate ligand, see: Ye & Zhang (2009); Zhang et al. (2005). For related structures, see: Zhang (2004, 2005, 2006a,b,c).

Experimental top

Pb(NO3)2 (0.331 g, 1.00 mmol) was dissolved in appropriate amount of water, and then 1M Na2CO3 solution was added. PbCO3 was obtained by filtration, which was then washed with distilled water for 5 times. The freshly prepared PbCO3, phen (0.050 g, 0.25 mmol), 2-fluorobenzoic acid (0.036 g, 0.25 mmol), CH3OH/H2O (v/v = 1:2, 15 ml) were mixed and stirred for 2 h. Subsequently, the resulting cream suspension was heated in a 23 ml Teflon-lined stainless steel autoclave at 433 K for 5 d. After the autoclave was cooled to room temperature, the solid was filtered off. The resulting filtrate was allowed to stand at room temperature, and evaporation for 2 weeks afforded colorless transparent block single crystals.

Refinement top

H atoms on C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and with Uiso(H) = 1.2Ueq(C). H atoms of water molecules were located in a difference Fourier map and refined with restraints of O—H = 0.85 (1) Å and Uiso(H) = 1.5Ueq(O). Two carboxylate O atoms (O1 and O2) and one F atom (F1) are each disordered over two sites with occupancy factors of 0.60 and 0.40. Two water molecules (O5 and O7) are half-occupied. The largest peak in the final difference Fourier map is 1.36 Å from atom Pb1 and the deepest hole is 0.97 Å from atom Pb1.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms and minor disordered O1', O2', F1' atoms have been omitted for clarity.
[Figure 2] Fig. 2. The π–π stacking interactions (dashed double arrows), with the mean interplanar distances of 3.44 (3) and 3.45 (3) Å.
Bis(2-fluorobenzoato-κ2O,O')bis(1,10- phenanthroline-κ2N,N')lead(II) dihydrate top
Crystal data top
[Pb(C7H4FO2)2(C12H8N2)2]·2H2OZ = 2
Mr = 881.83F(000) = 864
Triclinic, P1Dx = 1.704 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.406 (2) ÅCell parameters from 12091 reflections
b = 12.510 (3) Åθ = 3.0–25.0°
c = 13.771 (3) ŵ = 4.97 mm−1
α = 95.11 (3)°T = 290 K
β = 114.39 (3)°Block, colorless
γ = 101.72 (3)°0.29 × 0.18 × 0.17 mm
V = 1719.0 (9) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		6018 independent reflections
Radiation source: rotating anode4795 reflections with I > 2σ(I)
graphiteRint = 0.060
ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −13→13
Tmin = 0.353, Tmax = 0.428k = −14→14
13556 measured reflectionsl = −16→16
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.22 w = 1/[σ2(Fo2) + (0.0098P)2 + 16.8751P]
where P = (Fo2 + 2Fc2)/3
6018 reflections(Δ/σ)max = 0.001
484 parametersΔρmax = 2.12 e Å−3
0 restraintsΔρmin = −2.69 e Å−3
Crystal data top
[Pb(C7H4FO2)2(C12H8N2)2]·2H2Oγ = 101.72 (3)°
Mr = 881.83V = 1719.0 (9) Å3
Triclinic, P1Z = 2
a = 11.406 (2) ÅMo Kα radiation
b = 12.510 (3) ŵ = 4.97 mm−1
c = 13.771 (3) ÅT = 290 K
α = 95.11 (3)°0.29 × 0.18 × 0.17 mm
β = 114.39 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		6018 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4795 reflections with I > 2σ(I)
Tmin = 0.353, Tmax = 0.428Rint = 0.060
13556 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0098P)2 + 16.8751P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.136Δρmax = 2.12 e Å−3
S = 1.22Δρmin = −2.69 e Å−3
6018 reflectionsAbsolute structure: ?
484 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
H-atom parameters constrained
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Pb10.72835 (4)0.74410 (3)0.64620 (3)0.04239 (14)
N10.7303 (9)0.5537 (7)0.5424 (7)0.047 (2)
N20.8978 (8)0.7546 (7)0.5598 (7)0.047 (2)
N30.9155 (9)0.9162 (7)0.7848 (7)0.049 (2)
N40.9265 (8)0.7021 (6)0.7996 (6)0.043 (2)
O10.7104 (16)0.9221 (13)0.5375 (13)0.063 (4)0.60
O20.5878 (19)0.7499 (14)0.4192 (14)0.066 (5)0.60
O1'0.550 (3)0.775 (2)0.429 (2)0.063 (4)0.40
O2'0.644 (3)0.905 (2)0.529 (2)0.066 (5)0.40
O30.6374 (9)0.7678 (6)0.7949 (6)0.064 (2)
O40.6293 (8)0.5930 (6)0.7477 (6)0.057 (2)
O51.3159 (15)0.8677 (11)0.4039 (14)0.063 (5)0.50
H5A1.39340.86190.44410.095*0.50
H5B1.30750.92460.43650.095*0.50
O60.6197 (9)0.3730 (6)0.7780 (6)0.065 (2)
H6A0.58970.42270.74450.097*
H6B0.55110.32150.73510.097*
O71.1636 (14)0.6849 (11)0.2400 (11)0.044 (3)0.50
H7A1.22700.74200.27890.065*0.50
H7B1.17940.62450.22220.065*0.50
F10.507 (2)1.0371 (15)0.3788 (13)0.123 (6)0.60
F1'0.751 (3)0.812 (2)0.3143 (18)0.108 (8)0.40
F20.4355 (9)0.7192 (9)0.8787 (7)0.103 (3)
C10.6526 (12)0.4556 (9)0.5346 (9)0.055 (3)
H10.60460.45160.57530.066*
C20.6387 (12)0.3578 (10)0.4685 (9)0.059 (3)
H20.58500.29060.46750.071*
C30.7050 (12)0.3622 (10)0.4055 (10)0.061 (3)
H30.69430.29860.35890.073*
C40.7910 (11)0.4659 (9)0.4118 (8)0.051 (3)
C50.8669 (13)0.4762 (11)0.3518 (9)0.060 (3)
H50.85930.41400.30520.072*
C60.9475 (12)0.5716 (11)0.3607 (9)0.060 (3)
H60.99620.57560.32050.072*
C70.9620 (11)0.6705 (10)0.4319 (9)0.051 (3)
C81.0461 (12)0.7729 (11)0.4430 (10)0.064 (3)
H81.09330.78040.40160.077*
C91.0598 (13)0.8641 (11)0.5160 (11)0.070 (4)
H91.11910.93230.52720.084*
C100.9821 (11)0.8500 (9)0.5716 (9)0.056 (3)
H100.98980.91100.61970.068*
C110.8879 (10)0.6647 (9)0.4920 (7)0.042 (2)
C120.7996 (10)0.5592 (8)0.4811 (8)0.045 (2)
C130.6235 (13)0.8594 (10)0.4401 (9)0.057 (3)
C140.6234 (10)0.9175 (9)0.3497 (8)0.049 (3)
C150.5678 (14)1.0049 (11)0.3256 (10)0.069 (4)
H150.52541.02710.36580.082*0.40
C160.5713 (15)1.0614 (11)0.2456 (11)0.077 (4)
H160.53431.12140.23270.093*
C170.6316 (18)1.0260 (13)0.1851 (13)0.094 (5)
H170.63521.06240.13000.113*
C180.6857 (18)0.9391 (13)0.2050 (14)0.095 (5)
H180.72530.91540.16310.114*
C190.6820 (14)0.8858 (12)0.2871 (11)0.073 (4)
H190.72040.82660.30040.088*0.60
C210.9066 (12)1.0191 (9)0.7796 (9)0.059 (3)
H210.83351.03110.72260.071*
C221.0049 (13)1.1130 (9)0.8582 (10)0.058 (3)
H220.99721.18490.85200.070*
C231.1079 (14)1.0945 (11)0.9404 (11)0.068 (4)
H231.17211.15470.99260.081*
C241.1223 (12)0.9878 (10)0.9504 (9)0.054 (3)
C251.2286 (12)0.9633 (11)1.0367 (10)0.065 (3)
H251.29481.02161.09010.078*
C261.2368 (12)0.8607 (12)1.0439 (9)0.069 (4)
H261.30980.84851.10080.083*
C271.1343 (10)0.7660 (10)0.9648 (8)0.048 (3)
C281.1366 (11)0.6560 (10)0.9718 (9)0.055 (3)
H281.20720.64011.02810.066*
C291.0331 (12)0.5704 (10)0.8945 (9)0.057 (3)
H291.03080.49620.89820.068*
C300.9329 (10)0.6003 (8)0.8114 (8)0.044 (2)
H300.86380.54280.75920.052*
C311.0297 (10)0.7869 (8)0.8786 (8)0.044 (2)
C321.0205 (10)0.8983 (9)0.8695 (8)0.048 (3)
C330.6272 (10)0.6715 (8)0.8114 (8)0.040 (2)
C340.6202 (11)0.6488 (8)0.9125 (8)0.047 (3)
C350.5280 (12)0.6764 (10)0.9452 (10)0.057 (3)
C360.5325 (16)0.6643 (12)1.0452 (12)0.077 (4)
H360.47260.68751.06630.093*
C370.6264 (16)0.6175 (11)1.1134 (10)0.075 (4)
H370.62650.60461.17890.090*
C380.7195 (16)0.5900 (12)1.0850 (10)0.080 (4)
H380.78650.56311.13330.095*
C390.7147 (14)0.6022 (10)0.9849 (9)0.064 (3)
H390.77550.57890.96500.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.0453 (2)0.0421 (2)0.0347 (2)0.01148 (17)0.01311 (17)0.00643 (15)
N10.047 (5)0.040 (5)0.047 (5)−0.001 (4)0.016 (4)0.019 (4)
N20.042 (5)0.046 (5)0.057 (5)0.004 (4)0.030 (4)0.011 (4)
N30.061 (6)0.043 (5)0.048 (5)0.018 (4)0.024 (5)0.015 (4)
N40.053 (5)0.034 (4)0.041 (5)0.010 (4)0.020 (4)0.012 (4)
O10.076 (10)0.051 (7)0.056 (8)−0.002 (7)0.031 (8)0.022 (6)
O20.071 (11)0.057 (8)0.059 (8)0.016 (7)0.019 (7)0.004 (6)
O1'0.076 (10)0.051 (7)0.056 (8)−0.002 (7)0.031 (8)0.022 (6)
O2'0.071 (11)0.057 (8)0.059 (8)0.016 (7)0.019 (7)0.004 (6)
O30.100 (7)0.042 (4)0.053 (5)0.015 (4)0.038 (5)0.006 (4)
O40.070 (5)0.050 (4)0.050 (4)0.027 (4)0.021 (4)0.002 (4)
O50.049 (9)0.031 (7)0.120 (14)0.019 (7)0.041 (9)0.024 (8)
O60.077 (6)0.050 (5)0.056 (5)0.015 (4)0.021 (4)0.008 (4)
O70.058 (9)0.045 (8)0.059 (8)0.035 (7)0.043 (7)0.022 (7)
F10.173 (17)0.140 (15)0.122 (13)0.114 (14)0.085 (13)0.065 (11)
F1'0.14 (2)0.14 (2)0.115 (17)0.108 (18)0.086 (16)0.063 (15)
F20.092 (6)0.136 (8)0.105 (7)0.056 (6)0.052 (5)0.041 (6)
C10.061 (7)0.057 (7)0.046 (6)0.013 (6)0.022 (6)0.018 (5)
C20.057 (7)0.044 (6)0.059 (7)0.008 (6)0.011 (6)0.016 (6)
C30.066 (8)0.042 (6)0.056 (7)0.013 (6)0.011 (6)0.004 (5)
C40.046 (6)0.053 (7)0.030 (5)0.010 (5)−0.001 (5)0.001 (5)
C50.067 (8)0.062 (8)0.051 (7)0.022 (7)0.026 (6)0.002 (6)
C60.058 (7)0.084 (9)0.042 (6)0.019 (7)0.026 (6)0.006 (6)
C70.047 (6)0.059 (7)0.049 (6)0.015 (6)0.022 (5)0.011 (5)
C80.052 (7)0.083 (9)0.056 (7)0.004 (7)0.028 (6)0.012 (7)
C90.073 (9)0.058 (8)0.079 (9)−0.001 (7)0.041 (8)0.017 (7)
C100.056 (7)0.044 (6)0.059 (7)−0.003 (5)0.026 (6)−0.001 (5)
C110.043 (6)0.050 (6)0.032 (5)0.018 (5)0.012 (4)0.006 (4)
C120.049 (6)0.042 (6)0.040 (6)0.008 (5)0.017 (5)0.016 (5)
C130.068 (8)0.053 (7)0.039 (6)0.020 (6)0.011 (6)0.012 (5)
C140.039 (6)0.043 (6)0.040 (6)0.005 (5)−0.002 (5)0.001 (5)
C150.069 (8)0.065 (8)0.061 (8)0.028 (7)0.016 (7)0.001 (7)
C160.077 (9)0.052 (8)0.069 (9)0.013 (7)−0.001 (8)0.023 (7)
C170.134 (15)0.070 (10)0.089 (11)0.019 (10)0.057 (11)0.049 (9)
C180.126 (14)0.082 (11)0.110 (13)0.018 (10)0.085 (12)0.034 (10)
C190.082 (10)0.073 (9)0.081 (9)0.026 (8)0.046 (8)0.025 (7)
C210.062 (7)0.053 (7)0.054 (7)0.020 (6)0.015 (6)0.012 (6)
C220.074 (8)0.028 (5)0.064 (8)−0.004 (5)0.031 (7)0.006 (5)
C230.071 (9)0.057 (8)0.065 (8)0.009 (7)0.028 (7)−0.009 (6)
C240.057 (7)0.052 (7)0.057 (7)0.009 (6)0.032 (6)0.004 (5)
C250.057 (8)0.058 (8)0.050 (7)−0.002 (6)0.007 (6)−0.004 (6)
C260.045 (7)0.100 (11)0.033 (6)0.017 (7)−0.007 (5)−0.004 (6)
C270.040 (6)0.064 (7)0.034 (5)0.019 (5)0.008 (5)0.004 (5)
C280.048 (6)0.070 (8)0.041 (6)0.026 (6)0.008 (5)0.012 (6)
C290.063 (7)0.059 (7)0.054 (7)0.028 (6)0.023 (6)0.021 (6)
C300.040 (5)0.044 (6)0.033 (5)0.004 (5)0.008 (4)−0.001 (4)
C310.048 (6)0.043 (6)0.033 (5)0.006 (5)0.016 (5)−0.005 (4)
C320.042 (6)0.043 (6)0.045 (6)0.003 (5)0.015 (5)−0.013 (5)
C330.047 (6)0.039 (6)0.039 (5)0.009 (5)0.024 (5)0.009 (4)
C340.056 (6)0.029 (5)0.047 (6)0.001 (5)0.021 (5)0.002 (4)
C350.055 (7)0.057 (7)0.073 (8)0.015 (6)0.039 (6)0.030 (6)
C360.102 (11)0.078 (9)0.093 (10)0.035 (9)0.075 (9)0.030 (8)
C370.112 (12)0.061 (8)0.047 (7)0.009 (8)0.038 (8)0.001 (6)
C380.102 (11)0.087 (10)0.054 (8)0.038 (9)0.033 (8)0.018 (7)
C390.101 (10)0.058 (7)0.052 (7)0.024 (7)0.045 (7)0.029 (6)
Geometric parameters (Å, °) top
Pb1—N12.675 (9)C8—H80.9300
Pb1—N22.644 (8)C9—C101.387 (17)
Pb1—N32.622 (9)C9—H90.9300
Pb1—N42.566 (8)C10—H100.9300
Pb1—O12.788 (16)C11—C121.442 (15)
Pb1—O1'2.95 (3)C13—C141.496 (16)
Pb1—O22.880 (18)C14—C191.368 (17)
Pb1—O2'2.77 (3)C14—C151.372 (15)
Pb1—O32.670 (8)C15—C161.37 (2)
Pb1—O42.777 (9)C15—H150.9300
N1—C11.326 (14)C16—C171.38 (2)
N1—C121.372 (14)C16—H160.9300
N2—C101.321 (14)C17—C181.35 (2)
N2—C111.351 (12)C17—H170.9300
N3—C211.317 (13)C18—C191.37 (2)
N3—C321.359 (13)C18—H180.9300
N4—C301.310 (12)C19—H190.9300
N4—C311.387 (12)C21—C221.430 (15)
O1—C131.340 (19)C21—H210.9300
O2—C131.32 (2)C22—C231.332 (17)
O1'—C131.16 (3)C22—H220.9300
O2'—C131.22 (3)C23—C241.389 (17)
O3—C331.237 (12)C23—H230.9300
O4—C331.269 (11)C24—C251.415 (16)
O5—H5A0.85C24—C321.423 (15)
O5—H5B0.85C25—C261.314 (17)
O6—H6A0.85C25—H250.9300
O6—H6B0.85C26—C271.454 (16)
O7—H7A0.85C26—H260.9300
O7—H7B0.85C27—C311.383 (14)
F1—C151.289 (19)C27—C281.393 (15)
F1'—C191.32 (2)C28—C291.385 (16)
F2—C351.326 (13)C28—H280.9300
C1—C21.398 (15)C29—C301.388 (14)
C1—H10.9300C29—H290.9300
C2—C31.364 (18)C30—H300.9300
C2—H20.9300C31—C321.432 (14)
C3—C41.429 (17)C33—C341.475 (14)
C3—H30.9300C34—C351.394 (15)
C4—C121.401 (14)C34—C391.402 (16)
C4—C51.419 (17)C35—C361.379 (17)
C5—C61.311 (18)C36—C371.376 (19)
C5—H50.9300C36—H360.9300
C6—C71.445 (15)C37—C381.37 (2)
C6—H60.9300C37—H370.9300
C7—C81.389 (17)C38—C391.380 (17)
C7—C111.401 (15)C38—H380.9300
C8—C91.389 (17)C39—H390.9300
N4—Pb1—N363.5 (3)C9—C10—H10118.2
N4—Pb1—N279.2 (3)N2—C11—C7121.9 (10)
N3—Pb1—N282.0 (3)N2—C11—C12119.4 (9)
N4—Pb1—O384.9 (3)C7—C11—C12118.7 (9)
N3—Pb1—O379.9 (3)N1—C12—C4122.4 (10)
N2—Pb1—O3159.9 (3)N1—C12—C11118.3 (9)
N4—Pb1—N181.0 (2)C4—C12—C11119.3 (10)
N3—Pb1—N1133.9 (3)O1'—C13—O2'101 (2)
N2—Pb1—N162.4 (3)O2'—C13—O2116.8 (18)
O3—Pb1—N1127.2 (3)O1'—C13—O1123.3 (17)
N4—Pb1—O2'144.5 (6)O2—C13—O1124.4 (14)
N3—Pb1—O2'82.9 (6)O1'—C13—C14124.9 (17)
N2—Pb1—O2'85.4 (6)O2'—C13—C14125.0 (16)
O3—Pb1—O2'100.9 (6)O2—C13—C14117.9 (12)
N1—Pb1—O2'119.4 (6)O1—C13—C14111.5 (12)
N4—Pb1—O471.7 (3)C19—C14—C15116.4 (12)
N3—Pb1—O4112.5 (2)C19—C14—C13120.6 (10)
N2—Pb1—O4135.2 (2)C15—C14—C13123.0 (12)
O3—Pb1—O447.5 (2)F1—C15—C16116.5 (14)
N1—Pb1—O479.8 (2)F1—C15—C14119.9 (15)
O2'—Pb1—O4136.6 (6)C16—C15—C14123.6 (14)
N4—Pb1—O1131.7 (4)C16—C15—H15118.2
N3—Pb1—O174.0 (4)C14—C15—H15118.2
N2—Pb1—O173.0 (4)C15—C16—C17117.6 (13)
O3—Pb1—O1110.0 (4)C15—C16—H16121.2
N1—Pb1—O1117.3 (4)C17—C16—H16121.2
O2'—Pb1—O114.6 (6)C18—C17—C16120.7 (14)
O4—Pb1—O1150.7 (4)C18—C17—H17119.7
N4—Pb1—O2148.7 (4)C16—C17—H17119.7
N3—Pb1—O2121.6 (4)C17—C18—C19120.0 (15)
N2—Pb1—O271.7 (4)C17—C18—H18120.0
O3—Pb1—O2126.0 (4)C19—C18—H18120.0
N1—Pb1—O275.6 (3)F1'—C19—C14119.0 (15)
O2'—Pb1—O244.9 (6)F1'—C19—C18118.6 (16)
O4—Pb1—O2123.1 (4)C14—C19—C18121.8 (13)
O1—Pb1—O248.9 (5)C14—C19—H19119.1
N4—Pb1—O1'160.8 (6)C18—C19—H19119.1
N3—Pb1—O1'119.0 (6)N3—C21—C22122.6 (10)
N2—Pb1—O1'82.3 (6)N3—C21—H21118.7
O3—Pb1—O1'114.3 (6)C22—C21—H21118.7
N1—Pb1—O1'85.9 (6)C23—C22—C21118.1 (11)
O2'—Pb1—O1'37.3 (7)C23—C22—H22121.0
O4—Pb1—O1'119.8 (6)C21—C22—H22121.0
O1—Pb1—O1'45.0 (6)C22—C23—C24121.9 (11)
O2—Pb1—O1'12.3 (6)C22—C23—H23119.1
C1—N1—C12117.9 (9)C24—C23—H23119.1
C1—N1—Pb1123.0 (8)C23—C24—C25124.2 (11)
C12—N1—Pb1118.4 (6)C23—C24—C32117.0 (11)
C10—N2—C11118.8 (9)C25—C24—C32118.8 (11)
C10—N2—Pb1120.9 (7)C26—C25—C24122.1 (11)
C11—N2—Pb1119.8 (7)C26—C25—H25118.9
C21—N3—C32118.8 (9)C24—C25—H25118.9
C21—N3—Pb1122.2 (7)C25—C26—C27121.4 (10)
C32—N3—Pb1118.8 (6)C25—C26—H26119.3
C30—N4—C31116.2 (8)C27—C26—H26119.3
C30—N4—Pb1122.4 (6)C31—C27—C28118.8 (10)
C31—N4—Pb1121.3 (6)C31—C27—C26118.0 (10)
C13—O1—Pb194.8 (9)C28—C27—C26123.2 (10)
C13—O2—Pb191.3 (10)C29—C28—C27119.6 (9)
C13—O1'—Pb191.0 (17)C29—C28—H28120.2
C13—O2'—Pb198.8 (15)C27—C28—H28120.2
C33—O3—Pb196.9 (6)C28—C29—C30117.1 (10)
C33—O4—Pb191.0 (6)C28—C29—H29121.5
H5A—O5—H5B105.4C30—C29—H29121.5
H6A—O6—H6B92.6N4—C30—C29126.1 (10)
H7A—O7—H7B121.0N4—C30—H30117.0
N1—C1—C2123.7 (12)C29—C30—H30117.0
N1—C1—H1118.1C27—C31—N4122.3 (10)
C2—C1—H1118.1C27—C31—C32121.0 (9)
C3—C2—C1119.2 (12)N4—C31—C32116.7 (9)
C3—C2—H2120.4N3—C32—C24121.6 (10)
C1—C2—H2120.4N3—C32—C31119.7 (9)
C2—C3—C4119.2 (11)C24—C32—C31118.7 (10)
C2—C3—H3120.4O3—C33—O4122.5 (9)
C4—C3—H3120.4O3—C33—C34118.6 (9)
C12—C4—C5119.9 (11)O4—C33—C34118.8 (9)
C12—C4—C3117.6 (11)C35—C34—C39116.1 (11)
C5—C4—C3122.5 (11)C35—C34—C33123.8 (10)
C6—C5—C4121.5 (11)C39—C34—C33119.9 (10)
C6—C5—H5119.3F2—C35—C36119.3 (11)
C4—C5—H5119.3F2—C35—C34118.3 (11)
C5—C6—C7121.1 (11)C36—C35—C34122.4 (12)
C5—C6—H6119.4C37—C36—C35119.4 (12)
C7—C6—H6119.4C37—C36—H36120.3
C8—C7—C11117.9 (10)C35—C36—H36120.3
C8—C7—C6122.6 (11)C38—C37—C36120.1 (13)
C11—C7—C6119.5 (11)C38—C37—H37120.0
C9—C8—C7119.9 (12)C36—C37—H37120.0
C9—C8—H8120.0C37—C38—C39120.3 (13)
C7—C8—H8120.0C37—C38—H38119.8
C10—C9—C8117.7 (12)C39—C38—H38119.8
C10—C9—H9121.1C38—C39—C34121.5 (13)
C8—C9—H9121.1C38—C39—H39119.3
N2—C10—C9123.6 (11)C34—C39—H39119.3
N2—C10—H10118.2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O1'i0.852.343.027 (4)138
O5—H5A···F1ii0.852.332.801 (5)116
O5—H5A···O2'i0.852.513.313 (6)158
O5—H5B···O2'ii0.852.052.789 (3)146
O5—H5B···O1ii0.851.992.792 (6)158
O6—H6A···O40.852.082.807 (11)143
O6—H6B···O2iii0.852.032.795 (5)149
O6—H6B···O1'iii0.852.172.889 (5)143
O7—H7A···O50.851.972.75 (2)152
O7—H7B···O6iv0.852.292.810 (2)120
C8—H8···O50.932.543.344 (34)145
C16—H16···O3v0.932.543.422 (19)158
C21—H21···O10.932.443.106 (82)127
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y+2, −z+1.
Table 1
Selected geometric parameters (Å) top
Pb1—N12.675 (9)Pb1—O1'2.95 (3)
Pb1—N22.644 (8)Pb1—O22.880 (18)
Pb1—N32.622 (9)Pb1—O2'2.77 (3)
Pb1—N42.566 (8)Pb1—O32.670 (8)
Pb1—O12.788 (16)Pb1—O42.777 (9)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O1'i0.852.343.027 (4)138
O5—H5A···F1ii0.852.332.801 (5)116
O5—H5A···O2'i0.852.513.313 (6)158
O5—H5B···O2'ii0.852.052.789 (3)146
O5—H5B···O1ii0.851.992.792 (6)158
O6—H6A···O40.852.082.807 (11)143
O6—H6B···O2iii0.852.032.795 (5)149
O6—H6B···O1'iii0.852.172.889 (5)143
O7—H7A···O50.851.972.75 (2)152
O7—H7B···O6iv0.852.292.810 (2)120
C8—H8···O50.932.543.344 (34)145
C16—H16···O3v0.932.543.422 (19)158
C21—H21···O10.932.443.106 (82)127
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y+2, −z+1.
Acknowledgements top

The author gratefully acknowledges financial support from the Education Office of Zhejiang Province (grant No. 20051316).

references
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