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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 67| Part 8| August 2011| Pages m1057-m1058

catena-Poly[[[bis­­(4-ethyl­benzoato-κ2O,O′)lead(II)]-μ-nicotinamide-κ2N1:O] monohydrate]

aDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey, bDepartment of Physics, Karabük University, 78050 Karabük, Turkey, cDepartment of Chemistry, Atatürk University, 22240 Erzurum, Turkey, and dDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 28 June 2011; accepted 4 July 2011; online 9 July 2011)

In the crystal structure of the polymeric title compound, {[Pb(C9H9O2)2(C6H6N2O)]·H2O}n, the six-coordinate PbII ion is chelated by two 4-ethyl­benzoate (PEB) anions and is bridged by two nicotinamide (NA) ligands, forming a polymeric chain running along the b axis. The carboxyl­ate groups of the PEB ions are twisted away from the attached benzene rings by 4.0 (6) and 13.3 (5)°. The two benzene rings of the PEB ions bonded to the same metal ion are oriented at a dihedral angle of 87.4 (3)°. In the polymeric chain, the NA ligand is linked to one of the carboxyl­ate groups via N—H⋯O hydrogen bonding. In the crystal, adjacent polymeric chains inter­act via N—H⋯O and weak C—H⋯O hydrogen bonds; and the lattice water mol­ecule links with the polymeric chains via N—H⋯O and O—H⋯O hydrogen bonding. ππ stacking between the benzene and the pyridine rings [centroid–centroid distance = 3.805 (5) Å] and weak C—H⋯π inter­actions are also observed in the crystal structure.

Related literature

For niacin, see: Krishnamachari (1974[Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.]). For N,N-diethyl­nicotinamide, see: Bigoli et al. (1972[Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962-966.]). For related structures, see: Greenaway et al. (1984[Greenaway, F. T., Pezeshk, A., Cordes, A. W., Noble, M. C. & Sorenson, J. R. J. (1984). Inorg. Chim. Acta, 93, 67-71.]); Hökelek & Necefoğlu (1996[Hökelek, T. & Necefoğlu, H. (1996). Acta Cryst. C52, 1128-1131.]); Hökelek et al. (2009a[Hökelek, T., Yılmaz, F., Tercan, B., Gürgen, F. & Necefoğlu, H. (2009a). Acta Cryst. E65, m1416-m1417.],b[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009b). Acta Cryst. E65, m627-m628.],c[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009c). Acta Cryst. E65, m1037-m1038.],d[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009d). Acta Cryst. E65, m1365-m1366.], 2010[Hökelek, T., Dal, H., Tercan, B., Çimen, E. & Necefoğlu, H. (2010). Acta Cryst. E66, m953-m954.]).

[Scheme 1]

Experimental

Crystal data
  • [Pb(C9H9O2)2(C6H6N2O)]·H2O

  • Mr = 645.67

  • Triclinic, [P \overline 1]

  • a = 7.8093 (2) Å

  • b = 9.7950 (3) Å

  • c = 16.9380 (5) Å

  • α = 90.772 (2)°

  • β = 91.256 (2)°

  • γ = 106.916 (4)°

  • V = 1239.00 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 6.85 mm−1

  • T = 294 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Rigaku R-AXIS RAPID-S diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.211, Tmax = 0.358

  • 26925 measured reflections

  • 5076 independent reflections

  • 4208 reflections with I > 2σ(I)

  • Rint = 0.081

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.099

  • S = 1.06

  • 5076 reflections

  • 314 parameters

  • 5 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.11 e Å−3

  • Δρmin = −0.96 e Å−3

Table 1
Selected bond lengths (Å)

Pb1—O1 2.423 (5)
Pb1—O2 2.670 (5)
Pb1—O3 2.356 (5)
Pb1—O4 2.638 (5)
Pb1—O5 2.537 (5)
Pb1—N1 2.787 (5)

Table 2
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯O1 0.74 (17) 2.15 (16) 2.834 (8) 155 (19)
N2—H2B⋯O6 0.82 (16) 2.06 (15) 2.871 (9) 172 (15)
O6—H61⋯O2i 0.89 (5) 2.01 (7) 2.811 (8) 149 (7)
O6—H62⋯O3ii 0.90 (9) 1.93 (9) 2.822 (9) 169 (10)
C13—H13⋯O4iii 0.93 2.47 3.313 (11) 150
C19—H19⋯O6iv 0.93 2.43 3.323 (10) 162
C4—H4⋯Cgv 0.93 2.87 3.712 (8) 151
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) x+1, y, z; (iv) x, y-1, z; (v) -x+1, -y, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

In the crystal structure of the title compound, each PbII ion is coordinated by two 4-ethylbenzoate (PEB) and one nicotinamide (NA) ligands (Fig. 1), while symmetry related NA ligands bridge the PbII ions forming polymeric chains along the b axis (Fig. 2). The two PEB ions act as bidentate ligands, while the NA is monodentate ligand (Fig. 1). The crystal structures of similar complexes of CdII, CoII, MnII, ZnII and PbII ions, [Cd(C8H5O3)2(C6H6N2O)2(H2O)].H2O, (II) (Hökelek et al., 2009a), [Co(C9H10NO2)2(C6H6N2O)(H2O)2], (III) (Hökelek et al., 2009b), [Mn(C9H10NO2)2(C6H6N2O)(H2O)2], (IV) (Hökelek et al., 2009c), [Zn2(DENA)2(C7H5O3)4].2H2O, (V) (Hökelek & Necefoğlu, 1996), [Zn(C8H8NO2)2(C6H6N2O)2].H2O, (VI) (Hökelek et al., 2009d) and [Pb(C8H7O2)2(C6H6N2O)]n, (VII) (Hökelek et al., 2010), have also been reported. In (II) and (VII), the two benzoate ions are coordinated to the Cd and Pb atoms, respectively, as bidentate ligands. In the other structures one of the benzoate ligands acts as a bidentate ligand, while the other is monodentate ligand.

The average Pb—O bond length (Table 1) is 2.525 (5) Å and the Pb1 atom is displaced out of the least-squares planes of the carboxylate groups (O1/C1/O2) and (O3/C10/O4) by 0.1782 (3) Å and 0.3574 (3) Å, respectively. The O1/C1/O2 and O3/C9/O4 carboxylate planes form dihedral angles of 4.01 (63)° and 13.32 (53)°, respectively, with benzene rings A(C2-C7) and B(C11-C16), while the angles between rings A, B and C (N1/C19-C23) are A/B = 87.36 (26), A/C = 8.95 (22) and B/C = 78.76 (20)°. One of the intramolecular N-H···O hydrogen bonds (Table 2) links the NA ligand to the uncoordinated water molecule, while the other N-H···O hydrogen bond links the NA ligand to one of the carboxylate groups of the PEB ions acting as a bidentate ligand. In (I), the O1-Pb1-O2 and O3-Pb1-O4 angles are 51.10 (15)° and 51.95 (16)°, respectively. The corresponding O-M-O (where M is a metal) angles are 52.91 (4)° and 53.96 (4)° in (II), 60.70 (4)° in (III), 58.45 (9)° in (IV), 58.3 (3)° in (V), 60.03 (6)° in (VI), 51.09 (6)° and 51.71 (5)° in (VII) and 55.2 (1)° in [Cu(Asp)2(py)2] (where Asp is acetylsalicylate and py is pyridine) [(VIII); Greenaway et al., 1984].

In the crystal structure, N—H···O, O—H···O and C—H···O hydrogen bonds (Table 2) link adjacent chains into a two-dimensional network parallel to the bc plane. The π···π contact between the benzene and pyridine rings, Cg1—Cg3i, [symmetry code: (i) -x, -y, 1 - z, where Cg1 and Cg3 are the centroids of the rings A(C2-C7) and C (N1/C19-C23), respectively, may further stabilize the structure, with centroid-centroid distance of 3.805 (5) Å. There also exists a weak C—H···π interaction involving the benzene ring B(C11-C16) (Table 2).

Related literature top

For niacin, see: Krishnamachari (1974). For N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Greenaway et al. (1984); Hökelek & Necefoğlu (1996); Hökelek et al. (2009a,b,c,d, 2010).

Experimental top

The title compound was prepared by the reaction of Pb(NO3)2 (1.656 g, 5 mmol) in H2O (100 ml) and nicotinamide (1.220 g, 10 mmol) in H2O (50 ml) with sodium 4-ethylbenzoate (1.720 g, 10 mmol) in H2O (100 ml). The mixture was filtered and set aside to crystallize at ambient temperature for three weeks, giving colorless single crystals.

Refinement top

Atoms H2A and H2B (for NH2) and H61 and H62 (for H2O) were located in a difference Fourier map and refined isotropically. The C-bound H-atoms were positioned geometrically with C—H = 0.93, 0.97 and 0.96 Å, for aromatic, methylene and methyl H-atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = k × Ueq(C), where k = 1.5 for methyl H-atoms and k = 1.2 for all other H-atoms. The highest peak and deepest hole are located 0.94 and 0.90 Å, respectively, from Pb1.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Primed atoms are generated by the symmetry operators: (') x, 2 - y, z, ('') x, 1 - y, z. Dashed lines indicate the N—H···O hydrogen-bondings.
[Figure 2] Fig. 2. The crystal structure of the title complex.
catena-Poly[[[bis(4-ethylbenzoato-κ2O,O')lead(II)]- µ-nicotinamide-κ2N1:O] monohydrate] top
Crystal data top
[Pb(C9H9O2)2(C6H6N2O)]·H2OZ = 2
Mr = 645.67F(000) = 628
Triclinic, P1Dx = 1.731 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8093 (2) ÅCell parameters from 6051 reflections
b = 9.7950 (3) Åθ = 2.2–26.4°
c = 16.9380 (5) ŵ = 6.85 mm1
α = 90.772 (2)°T = 294 K
β = 91.256 (2)°Block, colorless
γ = 106.916 (4)°0.25 × 0.20 × 0.15 mm
V = 1239.00 (7) Å3
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
5076 independent reflections
Radiation source: fine-focus sealed tube4208 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
ω scansθmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan
(Blessing, 1995)
h = 99
Tmin = 0.211, Tmax = 0.358k = 1210
26925 measured reflectionsl = 2121
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0277P)2 + 1.8361P]
where P = (Fo2 + 2Fc2)/3
5076 reflections(Δ/σ)max < 0.001
314 parametersΔρmax = 1.11 e Å3
5 restraintsΔρmin = 0.96 e Å3
Crystal data top
[Pb(C9H9O2)2(C6H6N2O)]·H2Oγ = 106.916 (4)°
Mr = 645.67V = 1239.00 (7) Å3
Triclinic, P1Z = 2
a = 7.8093 (2) ÅMo Kα radiation
b = 9.7950 (3) ŵ = 6.85 mm1
c = 16.9380 (5) ÅT = 294 K
α = 90.772 (2)°0.25 × 0.20 × 0.15 mm
β = 91.256 (2)°
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
5076 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
4208 reflections with I > 2σ(I)
Tmin = 0.211, Tmax = 0.358Rint = 0.081
26925 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0435 restraints
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 1.11 e Å3
5076 reflectionsΔρmin = 0.96 e Å3
314 parameters
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.

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 > 2sigma(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
Pb10.08609 (4)0.15890 (3)0.394120 (15)0.05863 (12)
O10.2512 (8)0.2967 (5)0.5057 (3)0.0772 (15)
O20.2289 (7)0.0686 (5)0.5205 (3)0.0700 (13)
O30.3813 (6)0.2084 (5)0.3496 (3)0.0666 (12)
O40.1966 (7)0.1944 (5)0.2477 (3)0.0664 (12)
O50.0783 (8)0.4092 (5)0.3616 (3)0.0789 (15)
O60.3512 (9)0.8292 (6)0.5453 (4)0.0839 (17)
H610.347 (11)0.919 (4)0.550 (5)0.09 (3)*
H620.425 (11)0.808 (11)0.582 (5)0.14 (4)*
N10.0879 (8)0.1057 (6)0.3322 (3)0.0626 (15)
N20.2113 (10)0.5633 (7)0.4600 (4)0.0671 (17)
H2A0.24 (2)0.509 (17)0.482 (10)0.211*
H2B0.26 (2)0.640 (16)0.482 (9)0.211*
C10.2776 (9)0.1960 (8)0.5468 (4)0.0588 (17)
C20.3632 (9)0.2337 (7)0.6261 (4)0.0572 (16)
C30.3884 (10)0.1280 (8)0.6761 (4)0.0676 (19)
H30.35620.03360.65810.081*
C40.4593 (11)0.1614 (8)0.7507 (4)0.072 (2)
H40.47330.08930.78320.087*
C50.5101 (11)0.2995 (9)0.7782 (5)0.075 (2)
C60.4914 (12)0.4041 (9)0.7300 (5)0.086 (3)
H60.52870.49830.74830.103*
C70.4179 (10)0.3741 (7)0.6538 (4)0.0678 (19)
H70.40550.44730.62190.081*
C80.5923 (15)0.3367 (12)0.8615 (6)0.114 (4)
H8A0.63350.25840.88040.137*
H8B0.69540.42050.85930.137*
C90.465 (2)0.364 (2)0.9167 (8)0.226 (10)
H9A0.52760.40720.96440.339*
H9B0.37770.27610.92870.339*
H9C0.40620.42800.89340.339*
C100.3483 (10)0.2031 (7)0.2747 (4)0.0613 (17)
C110.4949 (9)0.2061 (7)0.2208 (4)0.0578 (16)
C120.6732 (10)0.2396 (8)0.2472 (4)0.0664 (19)
H120.70310.26320.30010.080*
C130.8050 (11)0.2375 (9)0.1947 (5)0.077 (2)
H130.92360.26240.21280.092*
C140.7663 (13)0.1999 (12)0.1170 (6)0.094 (3)
C150.5895 (13)0.1637 (11)0.0916 (5)0.095 (3)
H150.56030.13490.03920.114*
C160.4540 (11)0.1691 (9)0.1423 (5)0.078 (2)
H160.33630.14790.12340.094*
C170.9025 (19)0.166 (2)0.0606 (8)0.193 (9)
H17A0.98230.12210.08800.289*
H17B0.84300.10510.01660.289*
C180.997 (3)0.309 (3)0.0350 (13)0.328 (18)
H18A1.03790.30350.01770.491*
H18B1.09750.34980.07000.491*
H18C0.91720.36730.03560.491*
C190.1215 (9)0.2116 (7)0.3749 (4)0.0593 (17)
H190.16580.19090.42640.071*
C200.0926 (9)0.6504 (7)0.3452 (4)0.0573 (16)
C210.0247 (11)0.6222 (8)0.2695 (4)0.071 (2)
H210.00120.53070.24780.086*
C220.0087 (12)0.2704 (8)0.2257 (5)0.079 (2)
H220.05300.28800.17400.094*
C230.0241 (10)0.1386 (8)0.2593 (4)0.0654 (19)
H230.00030.06710.22930.079*
C240.1279 (9)0.5335 (7)0.3905 (4)0.0567 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.0721 (2)0.04518 (17)0.05984 (18)0.01901 (13)0.00048 (12)0.00349 (11)
O10.113 (4)0.062 (3)0.062 (3)0.034 (3)0.010 (3)0.005 (2)
O20.093 (4)0.055 (3)0.063 (3)0.025 (3)0.010 (3)0.001 (2)
O30.069 (3)0.068 (3)0.063 (3)0.020 (3)0.006 (2)0.003 (2)
O40.065 (3)0.069 (3)0.068 (3)0.024 (2)0.005 (2)0.011 (2)
O50.113 (4)0.040 (3)0.083 (4)0.023 (3)0.015 (3)0.003 (2)
O60.110 (5)0.062 (4)0.088 (4)0.043 (3)0.043 (3)0.020 (3)
N10.081 (4)0.046 (3)0.062 (4)0.022 (3)0.012 (3)0.001 (3)
N20.080 (4)0.054 (4)0.067 (4)0.019 (3)0.006 (3)0.000 (3)
C10.065 (4)0.053 (4)0.058 (4)0.017 (3)0.001 (3)0.006 (3)
C20.074 (5)0.044 (4)0.056 (4)0.020 (3)0.007 (3)0.009 (3)
C30.079 (5)0.065 (5)0.061 (4)0.025 (4)0.006 (4)0.003 (4)
C40.099 (6)0.059 (5)0.065 (5)0.032 (4)0.010 (4)0.011 (4)
C50.095 (6)0.063 (5)0.070 (5)0.030 (4)0.018 (4)0.004 (4)
C60.106 (7)0.053 (5)0.090 (6)0.012 (4)0.004 (5)0.018 (4)
C70.092 (6)0.044 (4)0.066 (5)0.019 (4)0.007 (4)0.007 (3)
C80.139 (10)0.119 (9)0.085 (7)0.042 (7)0.032 (6)0.025 (6)
C90.30 (2)0.36 (3)0.091 (10)0.21 (2)0.035 (12)0.051 (13)
C100.067 (5)0.052 (4)0.064 (5)0.016 (3)0.006 (4)0.001 (3)
C110.064 (4)0.056 (4)0.053 (4)0.018 (3)0.007 (3)0.002 (3)
C120.074 (5)0.064 (5)0.063 (4)0.022 (4)0.005 (4)0.001 (3)
C130.062 (5)0.094 (6)0.079 (6)0.031 (4)0.002 (4)0.000 (4)
C140.079 (6)0.126 (8)0.086 (6)0.042 (6)0.008 (5)0.000 (6)
C150.088 (7)0.148 (9)0.057 (5)0.046 (6)0.003 (4)0.004 (5)
C160.069 (5)0.099 (6)0.070 (5)0.030 (5)0.009 (4)0.009 (4)
C170.106 (11)0.36 (3)0.114 (11)0.072 (14)0.043 (8)0.046 (13)
C180.21 (3)0.60 (6)0.19 (2)0.14 (3)0.084 (18)0.05 (3)
C190.066 (4)0.047 (4)0.066 (4)0.020 (3)0.007 (3)0.006 (3)
C200.062 (4)0.048 (4)0.062 (4)0.016 (3)0.005 (3)0.001 (3)
C210.101 (6)0.048 (4)0.067 (5)0.025 (4)0.012 (4)0.007 (3)
C220.111 (7)0.060 (5)0.063 (5)0.024 (4)0.022 (4)0.004 (4)
C230.078 (5)0.056 (4)0.065 (5)0.025 (4)0.008 (4)0.008 (3)
C240.070 (5)0.034 (4)0.065 (4)0.014 (3)0.000 (3)0.010 (3)
Geometric parameters (Å, º) top
Pb1—O12.423 (5)C9—H9A0.9600
Pb1—O22.670 (5)C9—H9B0.9600
Pb1—O32.356 (5)C9—H9C0.9600
Pb1—O42.638 (5)C11—C101.474 (10)
Pb1—O52.537 (5)C11—C121.397 (10)
Pb1—N12.787 (5)C11—C161.379 (10)
Pb1—C12.924 (7)C12—C131.378 (10)
Pb1—C102.856 (8)C12—H120.9300
O1—C11.277 (8)C13—C141.365 (12)
O2—C11.266 (8)C13—H130.9300
O3—C101.286 (8)C14—C151.379 (12)
O4—C101.240 (8)C15—H150.9300
O5—C241.254 (8)C16—C151.390 (11)
O6—H610.89 (2)C16—H160.9300
O6—H620.90 (2)C17—C181.454 (17)
N1—C191.356 (8)C17—C141.547 (12)
N1—C231.320 (8)C17—H17A0.9700
N2—H2A0.72 (15)C17—H17B0.9700
N2—H2B0.82 (15)C18—H18A0.9600
C1—C21.479 (9)C18—H18B0.9600
C2—C31.400 (9)C18—H18C0.9600
C2—C71.388 (9)C19—C20i1.389 (9)
C3—C41.366 (10)C19—H190.9300
C3—H30.9300C20—C211.369 (10)
C4—C51.367 (10)C20—C19ii1.389 (9)
C4—H40.9300C21—C22ii1.377 (10)
C5—C61.358 (11)C21—H210.9300
C5—C81.530 (11)C22—C21i1.377 (10)
C6—H60.9300C22—H220.9300
C7—C61.393 (11)C23—C221.356 (10)
C7—H70.9300C23—H230.9300
C8—H8A0.9700C24—N21.320 (9)
C8—H8B0.9700C24—C201.474 (9)
C9—C81.458 (13)
O1—Pb1—O251.10 (15)C5—C8—H8B109.2
O1—Pb1—O4123.27 (17)C9—C8—C5112.2 (10)
O1—Pb1—O578.18 (17)C9—C8—H8A109.2
O1—Pb1—N1130.47 (17)C9—C8—H8B109.2
O1—Pb1—C125.49 (17)H8A—C8—H8B107.9
O1—Pb1—C10103.1 (2)C8—C9—H9A109.5
O2—Pb1—N182.33 (16)C8—C9—H9B109.5
O2—Pb1—C125.64 (16)C8—C9—H9C109.5
O2—Pb1—C10106.17 (19)H9A—C9—H9B109.5
O3—Pb1—O179.48 (18)H9A—C9—H9C109.5
O3—Pb1—O282.21 (16)H9B—C9—H9C109.5
O3—Pb1—O451.95 (16)O3—C10—Pb154.6 (4)
O3—Pb1—O591.12 (18)O3—C10—C11118.7 (6)
O3—Pb1—N178.26 (17)O4—C10—Pb167.3 (4)
O3—Pb1—C180.81 (18)O4—C10—O3121.3 (7)
O3—Pb1—C1026.41 (18)O4—C10—C11120.0 (7)
O4—Pb1—O2130.39 (15)C11—C10—Pb1169.6 (5)
O4—Pb1—N171.75 (16)C12—C11—C10122.1 (6)
O4—Pb1—C1132.48 (17)C16—C11—C10119.0 (7)
O4—Pb1—C1025.69 (17)C16—C11—C12118.8 (7)
O5—Pb1—O2129.25 (16)C11—C12—H12120.0
O5—Pb1—O475.76 (16)C13—C12—C11119.9 (7)
O5—Pb1—N1145.37 (17)C13—C12—H12120.0
O5—Pb1—C1103.61 (18)C12—C13—H13119.1
O5—Pb1—C1084.56 (19)C14—C13—C12121.9 (8)
N1—Pb1—C1106.98 (18)C14—C13—H13119.1
N1—Pb1—C1071.28 (19)C13—C14—C15118.0 (8)
C10—Pb1—C1107.2 (2)C13—C14—C17123.2 (10)
C1—O1—Pb199.8 (4)C15—C14—C17117.5 (10)
C1—O2—Pb188.4 (4)C14—C15—C16121.6 (8)
C10—O3—Pb199.0 (4)C14—C15—H15119.2
C10—O4—Pb187.0 (4)C16—C15—H15119.2
C24—O5—Pb1140.0 (5)C11—C16—C15119.7 (8)
H61—O6—H62113 (9)C11—C16—H16120.2
C19—N1—Pb1124.7 (4)C15—C16—H16120.2
C23—N1—Pb1117.3 (4)C14—C17—H17A111.6
C23—N1—C19117.0 (6)C14—C17—H17B111.6
C24—N2—H2A121 (10)C18—C17—C14100.7 (15)
C24—N2—H2B131 (10)C18—C17—H17A111.6
H2B—N2—H2A107 (10)C18—C17—H17B111.6
O1—C1—Pb154.8 (3)H17A—C17—H17B109.4
O1—C1—C2117.6 (6)C17—C18—H18A109.5
O2—C1—Pb165.9 (4)C17—C18—H18B109.5
O2—C1—O1120.6 (6)C17—C18—H18C109.5
O2—C1—C2121.8 (6)H18A—C18—H18B109.5
C2—C1—Pb1171.1 (5)H18A—C18—H18C109.5
C3—C2—C1120.9 (6)H18B—C18—H18C109.5
C7—C2—C1121.2 (6)N1—C19—C20i123.0 (6)
C7—C2—C3117.9 (6)N1—C19—H19118.5
C2—C3—H3119.4C20i—C19—H19118.5
C4—C3—C2121.1 (7)C19ii—C20—C24124.0 (6)
C4—C3—H3119.4C21—C20—C19ii117.3 (6)
C3—C4—C5120.7 (7)C21—C20—C24118.6 (6)
C3—C4—H4119.7C20—C21—C22ii119.9 (7)
C5—C4—H4119.7C20—C21—H21120.1
C4—C5—C8120.5 (8)C22ii—C21—H21120.1
C6—C5—C4119.2 (7)C21i—C22—H22120.6
C6—C5—C8120.3 (8)C23—C22—C21i118.8 (7)
C5—C6—C7121.8 (7)C23—C22—H22120.6
C5—C6—H6119.1N1—C23—C22123.9 (7)
C7—C6—H6119.1N1—C23—H23118.1
C2—C7—C6119.3 (7)C22—C23—H23118.1
C2—C7—H7120.4O5—C24—N2122.2 (6)
C6—C7—H7120.4O5—C24—C20119.0 (6)
C5—C8—H8A109.2N2—C24—C20118.9 (6)
O2—Pb1—O1—C12.2 (4)O4—Pb1—C10—C11136 (3)
O3—Pb1—O1—C190.7 (5)O5—Pb1—C10—O3103.7 (4)
O4—Pb1—O1—C1120.0 (4)O5—Pb1—C10—O468.2 (4)
O5—Pb1—O1—C1175.9 (5)O5—Pb1—C10—C11156 (3)
N1—Pb1—O1—C126.2 (5)N1—Pb1—C10—O3101.5 (4)
C10—Pb1—O1—C1102.6 (5)N1—Pb1—C10—O486.7 (4)
O1—Pb1—O2—C12.2 (4)N1—Pb1—C10—C1149 (3)
O3—Pb1—O2—C185.0 (4)C1—Pb1—C10—O31.1 (4)
O4—Pb1—O2—C1106.1 (4)C1—Pb1—C10—O4170.8 (4)
O5—Pb1—O2—C10.1 (5)C1—Pb1—C10—C1153 (3)
N1—Pb1—O2—C1164.1 (4)Pb1—O1—C1—O24.3 (8)
C10—Pb1—O2—C196.2 (4)Pb1—O1—C1—C2174.6 (5)
O1—Pb1—O3—C10153.1 (4)Pb1—O2—C1—O13.8 (7)
O2—Pb1—O3—C10155.1 (4)Pb1—O2—C1—C2175.0 (6)
O4—Pb1—O3—C104.5 (4)Pb1—O3—C10—O48.8 (7)
O5—Pb1—O3—C1075.4 (4)Pb1—O3—C10—C11170.6 (5)
N1—Pb1—O3—C1071.4 (4)Pb1—O4—C10—O37.8 (6)
C1—Pb1—O3—C10179.0 (4)Pb1—O4—C10—C11171.6 (6)
O1—Pb1—O4—C1042.4 (5)Pb1—O5—C24—N21.0 (13)
O2—Pb1—O4—C1022.3 (5)Pb1—O5—C24—C20178.7 (5)
O3—Pb1—O4—C104.6 (4)Pb1—N1—C19—C20i169.0 (5)
O5—Pb1—O4—C10107.6 (4)C23—N1—C19—C20i0.4 (11)
N1—Pb1—O4—C1084.6 (4)Pb1—N1—C23—C22169.6 (6)
C1—Pb1—O4—C1012.0 (5)C19—N1—C23—C220.1 (12)
O1—Pb1—O5—C242.5 (8)O1—C1—C2—C3176.8 (7)
O2—Pb1—O5—C240.7 (9)O1—C1—C2—C71.9 (11)
O3—Pb1—O5—C2481.5 (8)O2—C1—C2—C32.1 (11)
O4—Pb1—O5—C24131.7 (8)O2—C1—C2—C7179.2 (7)
N1—Pb1—O5—C24152.3 (7)C1—C2—C3—C4176.8 (7)
C1—Pb1—O5—C240.7 (8)C7—C2—C3—C42.0 (11)
C10—Pb1—O5—C24107.2 (8)C1—C2—C7—C6177.4 (7)
O1—Pb1—N1—C1929.5 (7)C3—C2—C7—C61.3 (11)
O1—Pb1—N1—C23161.8 (5)C2—C3—C4—C50.9 (13)
O2—Pb1—N1—C1910.9 (5)C3—C4—C5—C60.9 (14)
O2—Pb1—N1—C23179.6 (6)C3—C4—C5—C8179.0 (9)
O3—Pb1—N1—C1994.5 (6)C4—C5—C6—C71.6 (14)
O3—Pb1—N1—C2396.8 (5)C8—C5—C6—C7179.7 (9)
O4—Pb1—N1—C19148.1 (6)C4—C5—C8—C9103.5 (14)
O4—Pb1—N1—C2343.3 (5)C6—C5—C8—C978.5 (15)
O5—Pb1—N1—C19169.1 (5)C2—C7—C6—C50.5 (13)
O5—Pb1—N1—C2322.2 (7)C12—C11—C10—Pb159 (3)
C1—Pb1—N1—C1918.1 (6)C12—C11—C10—O311.5 (10)
C1—Pb1—N1—C23173.3 (5)C12—C11—C10—O4169.0 (7)
C10—Pb1—N1—C19121.0 (6)C16—C11—C10—Pb1119 (3)
C10—Pb1—N1—C2370.4 (5)C16—C11—C10—O3165.8 (7)
O1—Pb1—C1—O2176.0 (7)C16—C11—C10—O413.6 (10)
O2—Pb1—C1—O1176.0 (7)C16—C11—C12—C131.1 (11)
O3—Pb1—C1—O184.8 (5)C10—C11—C12—C13178.4 (7)
O3—Pb1—C1—O291.1 (4)C12—C11—C16—C151.0 (12)
O4—Pb1—C1—O178.9 (5)C10—C11—C16—C15176.4 (8)
O4—Pb1—C1—O297.0 (4)C11—C12—C13—C141.6 (13)
O5—Pb1—C1—O14.1 (5)C12—C13—C14—C150.1 (15)
O5—Pb1—C1—O2179.9 (4)C12—C13—C14—C17167.0 (11)
N1—Pb1—C1—O1159.5 (4)C13—C14—C15—C162.0 (16)
N1—Pb1—C1—O216.5 (4)C17—C14—C15—C16169.9 (11)
C10—Pb1—C1—O184.3 (5)C11—C16—C15—C142.6 (15)
C10—Pb1—C1—O291.6 (4)C18—C17—C14—C1385.6 (17)
O1—Pb1—C10—O327.2 (4)C18—C17—C14—C15107.2 (17)
O1—Pb1—C10—O4144.7 (4)C19ii—C20—C21—C22ii1.3 (12)
O1—Pb1—C10—C1179 (3)C24—C20—C21—C22ii179.7 (7)
O2—Pb1—C10—O325.7 (4)N1—C23—C22—C21i0.4 (13)
O2—Pb1—C10—O4162.5 (4)O5—C24—C20—C19ii171.9 (7)
O2—Pb1—C10—C1126 (3)O5—C24—C20—C217.1 (10)
O3—Pb1—C10—O4171.8 (7)N2—C24—C20—C19ii8.4 (11)
O3—Pb1—C10—C1152 (3)N2—C24—C20—C21172.7 (7)
O4—Pb1—C10—O3171.8 (7)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C11–C16 ring.
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.74 (17)2.15 (16)2.834 (8)155 (19)
N2—H2B···O60.82 (16)2.06 (15)2.871 (9)172 (15)
O6—H61···O2ii0.89 (5)2.01 (7)2.811 (8)149 (7)
O6—H62···O3iii0.90 (9)1.93 (9)2.822 (9)169 (10)
C13—H13···O4iv0.932.473.313 (11)150
C19—H19···O6i0.932.433.323 (10)162
C4—H4···Cgv0.932.873.712 (8)151
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z; (iii) x+1, y+1, z+1; (iv) x+1, y, z; (v) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula[Pb(C9H9O2)2(C6H6N2O)]·H2O
Mr645.67
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)7.8093 (2), 9.7950 (3), 16.9380 (5)
α, β, γ (°)90.772 (2), 91.256 (2), 106.916 (4)
V3)1239.00 (7)
Z2
Radiation typeMo Kα
µ (mm1)6.85
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerRigaku R-AXIS RAPID-S
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.211, 0.358
No. of measured, independent and
observed [I > 2σ(I)] reflections
26925, 5076, 4208
Rint0.081
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.099, 1.06
No. of reflections5076
No. of parameters314
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.11, 0.96

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Selected bond lengths (Å) top
Pb1—O12.423 (5)Pb1—O42.638 (5)
Pb1—O22.670 (5)Pb1—O52.537 (5)
Pb1—O32.356 (5)Pb1—N12.787 (5)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C11–C16 ring.
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.74 (17)2.15 (16)2.834 (8)155 (19)
N2—H2B···O60.82 (16)2.06 (15)2.871 (9)172 (15)
O6—H61···O2i0.89 (5)2.01 (7)2.811 (8)149 (7)
O6—H62···O3ii0.90 (9)1.93 (9)2.822 (9)169 (10)
C13—H13···O4iii0.932.473.313 (11)150
C19—H19···O6iv0.932.433.323 (10)162
C4—H4···Cgv0.932.873.712 (8)151
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z+1; (iii) x+1, y, z; (iv) x, y1, z; (v) x+1, y, z+1.
 

Acknowledgements

The authors are indebted to the Department of Chemistry, Atatürk University, Erzurum, Turkey, for the use of X-ray diffractometer purchased under grant No. 2003/219 of the University Research Fund.

References

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Volume 67| Part 8| August 2011| Pages m1057-m1058
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