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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 3| March 2012| Pages m257-m258

catena-Poly[[(μ-3-hy­dr­oxy­benzoato-κ3O1,O1′:O3)(μ-3-hy­dr­oxy­benzoato-κ3O1,O1′:O1)(isonicotinamide-κN1)­lead(II)] monohydrate]

aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, bDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 1 February 2012; accepted 2 February 2012; online 10 February 2012)

In the crystal of the title polymeric compound, {[Pb(C7H5O3)2(C6H6N2O)]·H2O}n, the PbII ion is chelated by two carboxyl­ate groups of 3-hy­droxy­benzoate (HB) anions, and coordinated by one isonicotinamide mol­ecule; a carboxyl­ate O atom and a hy­droxy O atom from adjacent HB anions bridge the PbII ion to form polymeric chains along [100], in which the PbII ion is in an irregular seven-coordination geometry. The carboxyl­ate groups of the HB ions are slightly twisted away from the attached benzene rings by 2.84 (15) and 4.8 (2)°. The planes of the two benzene rings of the HB ions are oriented with respect to each other at a dihedral angle of 84.41 (8)°. In the crystal, adjacent polymeric chains inter­act via O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen bonds. The solvent water mol­ecule links with the polymeric chains via O—H⋯O hydrogen bonding. ππ stacking between the benzene and pyridine rings and between the benzene rings [centroid–centroid distances = 3.731 (2) and 3.353 (2) Å] are present in the crystal.

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, Yılmaz et al. (2009[Hökelek, T., Yılmaz, F., Tercan, B., Gürgen, F. & Necefoğlu, H. (2009). Acta Cryst. E65, m1416-m1417.]); Hökelek, Dal et al. (2009a[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009a). Acta Cryst. E65, m627-m628.],b[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009b). Acta Cryst. E65, m1037-m1038.],c[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2009c). Acta Cryst. E65, m1365-m1366.], 2010[Hökelek, T., Dal, H., Tercan, B., Çimen, E. & Necefoğlu, H. (2010). Acta Cryst. E66, m953-m954.]); Hökelek, Süzen et al. (2010[Hökelek, T., Süzen, Y., Tercan, B., Aybirdi, Ö. & Necefoğlu, H. (2010). Acta Cryst. E66, m782-m783.]); Hökelek et al. (2011[Hökelek, T., Tercan, B., Şahin, E., Aktaş, V. & Necefoğlu, H. (2011). Acta Cryst. E67, m1057-m1058.]).

[Scheme 1]

Experimental

Crystal data
  • [Pb(C7H5O3)2(C6H6N2O)]·H2O

  • Mr = 621.56

  • Triclinic, [P \overline 1]

  • a = 7.3626 (2) Å

  • b = 12.1382 (3) Å

  • c = 12.1789 (3) Å

  • α = 67.165 (2)°

  • β = 74.192 (3)°

  • γ = 88.921 (3)°

  • V = 960.53 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 8.84 mm−1

  • T = 100 K

  • 0.26 × 0.14 × 0.13 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.395, Tmax = 0.603

  • 17040 measured reflections

  • 4783 independent reflections

  • 4652 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.017

  • wR(F2) = 0.050

  • S = 1.19

  • 4783 reflections

  • 304 parameters

  • 4 restraints

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

  • Δρmax = 0.94 e Å−3

  • Δρmin = −1.27 e Å−3

Table 1
Selected bond lengths (Å)

Pb1—N1 2.564 (2)
Pb1—O1 2.753 (2)
Pb1—O2 2.317 (2)
Pb1—O3i 2.899 (2)
Pb1—O4 2.742 (2)
Pb1—O5 2.344 (2)
Pb1—O5ii 2.954 (2)
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+2, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H21⋯O4iii 0.84 (4) 2.21 (4) 3.046 (3) 175 (4)
N2—H22⋯O8iv 0.85 (4) 2.06 (4) 2.880 (5) 162 (4)
O3—H31⋯O7v 0.86 (5) 1.81 (5) 2.646 (3) 166 (4)
O6—H61⋯O1vi 0.73 (6) 2.05 (6) 2.755 (4) 161 (6)
O8—H81⋯O6vii 0.89 (4) 2.02 (4) 2.846 (3) 154 (4)
O8—H82⋯O2viii 0.87 (5) 2.31 (5) 3.018 (3) 139 (5)
O8—H82⋯O3ix 0.87 (5) 2.44 (6) 3.054 (3) 128 (4)
C12—H12⋯O1vi 0.93 2.57 3.269 (4) 132
C15—H15⋯O5 0.93 2.46 3.060 (4) 122
C16—H16⋯O8iv 0.93 2.51 3.413 (4) 165
Symmetry codes: (iii) x+1, y, z-1; (iv) x+1, y+1, z-1; (v) x, y, z+1; (vi) x, y+1, z; (vii) x, y-1, z; (viii) -x, -y+1, -z+1; (ix) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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 polymeric title compound, (I), the PbII ion is chelated by two carboxyl groups of 3-hydroxybenzoate (HB) anions, and coordinated by one isonicotinamide (INA) molecule (Fig. 1); a carboxyl-O atom and a hydroxyl-O atom from adjacent HB anions bridge the PbII ion to form the polymeric complex, in which the PbII ion is in an irregular seven-coordination geometry (Fig. 2). The two HB ions act as bidentate ligands, while the INA is monodentate ligand (Fig. 1).

The average Pb-O bond length (Table 1) is 2.539 (2) Å, and the Pb atom is displaced out of the least-squares planes of the carboxylate groups (O1/C1/O2) and (O4/C8/O5) by -0.0641 (1) and -0.0110 (1) Å, respectively. In (I), the O1-Pb1-O2 and O4-Pb1-O5 angles are 51.00 (6) and 50.94 (6) °, respectively. The corresponding O-M-O (where M is a metal) angles are 51.10 (15)° and 51.95 (16)° in {[Pb(PEB)2(NA)].H2O}n (Hökelek et al., 2011), 51.09 (6)° and 51.71 (5)° in [Pb(PMB)2(NA)]n (Hökelek, Dal et al., 2010), 55.96 (4)° and 53.78 (4)° in [Cd2(DMAB)4(NA)2(H2O)2] (Hökelek, Süzen et al., 2010), 52.91 (4)° and 53.96 (4)° in [Cd(FB)2(INA)2(H2O)].H2O (Hökelek, Yılmaz et al., 2009), 60.70 (4)° in [Co(DMAB)2(INA)(H2O)2] (Hökelek, Dal et al., 2009a), 58.45 (9)° in [Mn(DMAB)2(INA)(H2O)2] (Hökelek, Dal et al., 2009b), 60.03 (6)° in [Zn(MAB)2(INA)2].H2O (Hökelek, Dal et al., 2009c), 58.3 (3)° in [Zn2(DENA)2(HB)4].2H2O (Hökelek & 'Necefoğlu, 1996) [where NA, INA, DENA, HB, FB, MAB, PMB, PEB and DMAB are nicotinamide, isonicotinamide, N,N-diethylnicotinamide, 4-hydroxybenzoate, 4-formylbenzoate, 4-methylaminobenzoate, 4-methylbenzoate, 4-ethylbenzoate and 4-dimethylaminobenzoate, respectively] and 55.2 (1)° in [Cu(Asp)2(py)2] (where Asp is acetylsalicylate and py is pyridine) (Greenaway et al., 1984).

The dihedral angles between the planar carboxylate groups and the adjacent benzene rings A (C2-C7) and B (C9-C14) are 2.84 (15) and 4.8 (2) °, respectively, while those between rings A, B, C (N1/C15-C19), D (Pb1/O1/O2/C1) and E (Pb1/O4/O5/C8) are A/B = 84.41 (8), A/C = 87.69 (7), B/C = 10.23 (9) and D/E = 80.12 (9)°.

In the crystal, adjacent polymeric chains interact via O—H···O, N—H···O and weak C—H···O hydrogen bonds; and the lattice water molecule links with the polymeric chains via O—H···O hydrogen bonding (Table 2), in which they may be effective in the stabilization of the structure. π···π Contacts between the benzene and pyridine rings and between the benzene rings, Cg3—Cg2i and Cg1—Cg1ii [symmetry codes: (i) 1 - x, 2 - y, -z, (ii) 1 - x, 1 - y, 1 - z, where Cg1, Cg2 and Cg3 are the centroids of the rings A (C2-C7), B (C9-C14) and C (N1/C15-C19), respectively] may further stabilize the structure, with centroid-centroid distances of 3.731 (2) and 3.353 (2) Å, respectively.

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 & Necefouglu (1996); Hökelek, Yılmaz et al. (2009); Hökelek, Dal et al. (2009a,b,c, 2010); Hökelek, Süzen et al. (2010); Hökelek et al. (2011).

Experimental top

The title compound was prepared by the reaction of Pb(NO3)2 (1.656 g, 5 mmol) in H2O (100 ml) and INA (1.220 g, 10 mmol) in H2O (50 ml) with sodium 3-hydroxybenzoate (1.601 g, 10 mmol) in H2O (100 ml). The mixture was filtered and set aside to crystallize at ambient temperature for two weeks, giving yellow single crystals.

Refinement top

Atoms H81 and H82 (for H2O), H21 and H22 (for NH2) and H31 and H61 (for OH) were located in a difference Fourier map and were refined isotropically. The C-bound H-atoms were positioned geometrically with C—H = 0.93 Å and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The polymeric structure.
catena-Poly[[(µ-3-hydroxybenzoato- κ3O1,O1':O3)(µ-3-hydroxybenzoato- κ3O1,O1':O1)(isonicotinamide- κN1)lead(II)] monohydrate] top
Crystal data top
[Pb(C7H5O3)2(C6H6N2O)]·H2OZ = 2
Mr = 621.56F(000) = 596
Triclinic, P1Dx = 2.149 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3626 (2) ÅCell parameters from 9959 reflections
b = 12.1382 (3) Åθ = 2.9–28.5°
c = 12.1789 (3) ŵ = 8.84 mm1
α = 67.165 (2)°T = 100 K
β = 74.192 (3)°Block, yellow
γ = 88.921 (3)°0.26 × 0.14 × 0.13 mm
V = 960.53 (5) Å3
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
4783 independent reflections
Radiation source: fine-focus sealed tube4652 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 28.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 99
Tmin = 0.395, Tmax = 0.603k = 1616
17040 measured reflectionsl = 1616
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)] = 0.017Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.050H atoms treated by a mixture of independent and constrained refinement
S = 1.19 w = 1/[σ2(Fo2) + (0.0228P)2 + 0.6812P]
where P = (Fo2 + 2Fc2)/3
4783 reflections(Δ/σ)max = 0.001
304 parametersΔρmax = 0.94 e Å3
4 restraintsΔρmin = 1.27 e Å3
Crystal data top
[Pb(C7H5O3)2(C6H6N2O)]·H2Oγ = 88.921 (3)°
Mr = 621.56V = 960.53 (5) Å3
Triclinic, P1Z = 2
a = 7.3626 (2) ÅMo Kα radiation
b = 12.1382 (3) ŵ = 8.84 mm1
c = 12.1789 (3) ÅT = 100 K
α = 67.165 (2)°0.26 × 0.14 × 0.13 mm
β = 74.192 (3)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
4783 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
4652 reflections with I > 2σ(I)
Tmin = 0.395, Tmax = 0.603Rint = 0.032
17040 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0174 restraints
wR(F2) = 0.050H atoms treated by a mixture of independent and constrained refinement
S = 1.19Δρmax = 0.94 e Å3
4783 reflectionsΔρmin = 1.27 e Å3
304 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
Pb10.030913 (12)0.835470 (8)0.138812 (8)0.00786 (4)
O10.1928 (3)0.62307 (19)0.21830 (19)0.0120 (4)
O20.2876 (3)0.79500 (18)0.21917 (19)0.0119 (4)
O30.8367 (3)0.7102 (2)0.40132 (19)0.0124 (4)
H310.765 (6)0.748 (4)0.440 (4)0.024 (10)*
O40.0065 (3)0.98903 (19)0.25722 (19)0.0136 (4)
O50.1523 (3)1.03718 (18)0.05741 (18)0.0110 (4)
O60.0703 (3)1.3836 (2)0.3029 (2)0.0136 (4)
H610.111 (7)1.442 (5)0.294 (5)0.042 (15)*
O70.6149 (3)0.7967 (2)0.4465 (2)0.0172 (5)
O80.1509 (3)0.1982 (2)0.5265 (2)0.0168 (4)
H810.066 (6)0.260 (3)0.473 (4)0.057 (16)*
H820.127 (8)0.204 (5)0.590 (4)0.062 (17)*
N10.2801 (3)0.8592 (2)0.0646 (2)0.0106 (5)
N20.7553 (4)0.9791 (3)0.4941 (2)0.0144 (5)
H210.830 (5)0.981 (4)0.561 (3)0.039 (13)*
H220.769 (6)1.035 (3)0.471 (4)0.028 (11)*
C10.3015 (4)0.6828 (3)0.2424 (2)0.0088 (5)
C20.4561 (4)0.6274 (2)0.2976 (2)0.0090 (5)
C30.5721 (4)0.6960 (3)0.3251 (2)0.0093 (5)
H30.55290.77590.30980.011*
C40.7168 (4)0.6450 (3)0.3754 (2)0.0096 (5)
C50.7482 (4)0.5263 (3)0.3954 (2)0.0109 (5)
H50.84810.49310.42620.013*
C60.6310 (4)0.4575 (3)0.3697 (3)0.0112 (5)
H60.65020.37750.38530.013*
C70.4846 (4)0.5077 (3)0.3203 (2)0.0096 (5)
H70.40630.46170.30260.012*
C80.0990 (4)1.0640 (3)0.1532 (3)0.0091 (5)
C90.1525 (4)1.1908 (3)0.1322 (3)0.0091 (5)
C100.0883 (4)1.2299 (3)0.2284 (3)0.0094 (5)
H100.01491.17700.30630.011*
C110.1341 (4)1.3476 (3)0.2076 (3)0.0103 (5)
C120.2455 (5)1.4274 (3)0.0911 (3)0.0178 (6)
H120.27561.50670.07710.021*
C130.3106 (5)1.3867 (3)0.0033 (3)0.0222 (7)
H130.38561.43920.08080.027*
C140.2653 (4)1.2688 (3)0.0164 (3)0.0154 (6)
H140.31011.24220.04730.019*
C150.4005 (4)0.9580 (3)0.1397 (3)0.0118 (5)
H150.40601.01940.11280.014*
C160.5163 (4)0.9719 (3)0.2555 (3)0.0118 (5)
H160.59591.04220.30580.014*
C170.5126 (4)0.8796 (3)0.2960 (3)0.0094 (5)
C180.3894 (4)0.7765 (3)0.2170 (3)0.0127 (5)
H180.38320.71270.24060.015*
C190.2766 (4)0.7705 (3)0.1032 (3)0.0116 (5)
H190.19460.70160.05120.014*
C200.6331 (4)0.8831 (3)0.4197 (3)0.0110 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.00963 (6)0.00600 (6)0.00604 (6)0.00059 (4)0.00152 (4)0.00083 (4)
O10.0153 (9)0.0070 (10)0.0142 (10)0.0003 (7)0.0053 (8)0.0041 (8)
O20.0148 (9)0.0063 (10)0.0158 (10)0.0004 (7)0.0071 (8)0.0038 (8)
O30.0131 (9)0.0132 (11)0.0127 (10)0.0004 (8)0.0023 (8)0.0078 (9)
O40.0191 (10)0.0097 (11)0.0091 (9)0.0018 (8)0.0011 (8)0.0024 (8)
O50.0159 (9)0.0092 (10)0.0087 (9)0.0010 (7)0.0028 (7)0.0051 (8)
O60.0170 (10)0.0095 (11)0.0140 (10)0.0022 (8)0.0014 (8)0.0082 (9)
O70.0193 (10)0.0158 (12)0.0166 (11)0.0039 (8)0.0024 (8)0.0113 (9)
O80.0231 (11)0.0151 (12)0.0097 (10)0.0060 (9)0.0013 (8)0.0042 (9)
N10.0095 (10)0.0100 (12)0.0088 (11)0.0013 (9)0.0002 (8)0.0019 (9)
N20.0185 (12)0.0136 (13)0.0096 (12)0.0024 (10)0.0021 (9)0.0071 (10)
C10.0103 (11)0.0079 (13)0.0056 (12)0.0003 (9)0.0005 (9)0.0019 (10)
C20.0117 (12)0.0067 (13)0.0059 (12)0.0004 (9)0.0002 (9)0.0013 (10)
C30.0122 (12)0.0058 (13)0.0068 (12)0.0008 (9)0.0012 (9)0.0017 (10)
C40.0101 (12)0.0117 (14)0.0047 (11)0.0016 (10)0.0007 (9)0.0027 (10)
C50.0124 (12)0.0118 (14)0.0058 (12)0.0014 (10)0.0003 (9)0.0023 (11)
C60.0157 (13)0.0072 (13)0.0091 (12)0.0014 (10)0.0017 (10)0.0027 (11)
C70.0121 (12)0.0075 (13)0.0083 (12)0.0011 (10)0.0011 (9)0.0033 (10)
C80.0087 (11)0.0084 (13)0.0094 (12)0.0001 (9)0.0023 (9)0.0029 (11)
C90.0109 (12)0.0067 (13)0.0088 (12)0.0001 (9)0.0031 (10)0.0020 (10)
C100.0111 (12)0.0063 (13)0.0072 (12)0.0012 (10)0.0011 (9)0.0001 (10)
C110.0113 (12)0.0105 (14)0.0102 (13)0.0017 (10)0.0033 (10)0.0051 (11)
C120.0259 (15)0.0104 (15)0.0129 (14)0.0044 (12)0.0012 (12)0.0030 (12)
C130.0323 (17)0.0158 (17)0.0103 (14)0.0101 (13)0.0053 (12)0.0039 (13)
C140.0206 (14)0.0138 (15)0.0094 (13)0.0041 (11)0.0001 (11)0.0046 (12)
C150.0135 (12)0.0093 (14)0.0128 (13)0.0011 (10)0.0022 (10)0.0058 (11)
C160.0112 (12)0.0094 (14)0.0113 (13)0.0018 (10)0.0002 (10)0.0021 (11)
C170.0092 (11)0.0096 (14)0.0087 (12)0.0005 (10)0.0017 (10)0.0033 (11)
C180.0132 (12)0.0109 (14)0.0145 (14)0.0007 (10)0.0020 (10)0.0069 (12)
C190.0136 (12)0.0068 (13)0.0119 (13)0.0019 (10)0.0019 (10)0.0022 (11)
C200.0113 (12)0.0107 (14)0.0097 (13)0.0004 (10)0.0014 (10)0.0037 (11)
Geometric parameters (Å, º) top
Pb1—N12.564 (2)C5—C41.390 (4)
Pb1—O12.753 (2)C5—C61.386 (4)
Pb1—O22.317 (2)C5—H50.9300
Pb1—O3i2.899 (2)C6—H60.9300
Pb1—O42.742 (2)C7—C21.393 (4)
Pb1—O52.344 (2)C7—C61.393 (4)
Pb1—O5ii2.954 (2)C7—H70.9300
O1—C11.253 (3)C9—C141.390 (4)
O2—C11.287 (3)C8—C91.501 (4)
O3—C41.370 (3)C10—C91.394 (4)
O3—H310.86 (4)C10—H100.9300
O4—C81.247 (3)C11—C101.382 (4)
O5—C81.288 (3)C11—C121.397 (4)
O6—C111.361 (3)C12—C131.389 (4)
O6—H610.73 (5)C12—H120.9300
O7—C201.234 (4)C13—C141.387 (4)
O8—H810.89 (2)C13—H130.9300
O8—H820.87 (2)C14—H140.9300
N1—C151.344 (4)C15—H150.9300
N1—C191.334 (4)C16—C151.382 (4)
N2—C201.328 (4)C16—H160.9300
N2—H210.844 (19)C17—C161.391 (4)
N2—H220.843 (19)C17—C181.396 (4)
C1—C21.495 (4)C17—C201.510 (4)
C3—C21.390 (4)C18—H180.9300
C3—C41.390 (4)C19—C181.383 (4)
C3—H30.9300C19—H190.9300
O2—Pb1—O151.00 (6)C2—C7—H7120.2
O2—Pb1—O477.71 (7)C6—C7—H7120.2
O2—Pb1—O585.33 (7)O4—C8—O5121.9 (3)
O2—Pb1—N183.32 (7)O4—C8—C9121.8 (2)
O4—Pb1—O1121.06 (6)O5—C8—C9116.3 (2)
O5—Pb1—O1132.63 (6)C10—C9—C8120.0 (2)
O5—Pb1—O450.94 (6)C14—C9—C8119.6 (2)
O5—Pb1—N177.24 (7)C14—C9—C10120.4 (3)
N1—Pb1—O179.96 (7)C11—C10—C9119.7 (3)
N1—Pb1—O4125.57 (7)C11—C10—H10120.1
C1—O1—Pb183.85 (16)C9—C10—H10120.1
C1—O2—Pb1103.41 (16)O6—C11—C10118.7 (3)
C4—O3—H31105 (3)O6—C11—C12120.8 (3)
C8—O4—Pb184.76 (16)C10—C11—C12120.5 (3)
C8—O5—Pb1102.42 (17)C11—C12—H12120.5
C11—O6—H61116 (4)C13—C12—C11119.1 (3)
H82—O8—H8192 (5)C13—C12—H12120.5
C15—N1—Pb1124.95 (18)C12—C13—H13119.5
C19—N1—Pb1116.64 (18)C14—C13—C12120.9 (3)
C19—N1—C15118.1 (2)C14—C13—H13119.5
C20—N2—H21120 (3)C9—C14—H14120.3
C20—N2—H22120 (3)C13—C14—C9119.3 (3)
H22—N2—H21119 (4)C13—C14—H14120.3
O1—C1—O2121.7 (2)N1—C15—C16122.6 (3)
O1—C1—C2121.4 (2)N1—C15—H15118.7
O2—C1—C2116.9 (2)C16—C15—H15118.7
C3—C2—C1119.8 (2)C15—C16—C17119.3 (3)
C3—C2—C7120.2 (3)C15—C16—H16120.3
C7—C2—C1120.0 (2)C17—C16—H16120.3
C2—C3—H3120.0C16—C17—C18117.9 (2)
C4—C3—C2120.0 (3)C16—C17—C20124.5 (3)
C4—C3—H3120.0C18—C17—C20117.6 (3)
O3—C4—C3121.7 (3)C17—C18—H18120.5
O3—C4—C5118.3 (2)C19—C18—C17119.1 (3)
C3—C4—C5119.9 (3)C19—C18—H18120.5
C4—C5—H5119.9N1—C19—C18123.0 (3)
C6—C5—C4120.1 (3)N1—C19—H19118.5
C6—C5—H5119.9C18—C19—H19118.5
C5—C6—C7120.2 (3)O7—C20—N2123.1 (3)
C5—C6—H6119.9O7—C20—C17118.7 (3)
C7—C6—H6119.9N2—C20—C17118.2 (3)
C2—C7—C6119.6 (3)
O2—Pb1—O1—C10.82 (14)O1—C1—C2—C71.7 (4)
O4—Pb1—O1—C135.34 (17)O2—C1—C2—C32.1 (4)
O5—Pb1—O1—C128.21 (18)O2—C1—C2—C7177.3 (2)
N1—Pb1—O1—C190.32 (16)C4—C3—C2—C70.1 (4)
O1—Pb1—O2—C10.81 (14)C4—C3—C2—C1179.5 (2)
O4—Pb1—O2—C1148.04 (17)C2—C3—C4—O3178.6 (2)
O5—Pb1—O2—C1160.96 (16)C2—C3—C4—C51.6 (4)
N1—Pb1—O2—C183.29 (16)C6—C5—C4—O3179.6 (2)
O1—Pb1—O4—C8122.11 (16)C6—C5—C4—C32.4 (4)
O2—Pb1—O4—C894.12 (16)C4—C5—C6—C71.8 (4)
O5—Pb1—O4—C80.14 (15)C6—C7—C2—C1178.8 (2)
N1—Pb1—O4—C821.70 (19)C6—C7—C2—C30.6 (4)
O1—Pb1—O5—C899.11 (17)C2—C7—C6—C50.3 (4)
O2—Pb1—O5—C878.09 (16)O4—C8—C9—C104.2 (4)
O4—Pb1—O5—C80.13 (15)O4—C8—C9—C14176.1 (3)
N1—Pb1—O5—C8162.28 (17)O5—C8—C9—C10175.1 (2)
O1—Pb1—N1—C15132.2 (2)O5—C8—C9—C144.5 (4)
O1—Pb1—N1—C1954.3 (2)C8—C9—C14—C13178.5 (3)
O2—Pb1—N1—C1580.7 (2)C10—C9—C14—C131.2 (5)
O2—Pb1—N1—C19105.8 (2)C11—C10—C9—C141.3 (4)
O4—Pb1—N1—C1511.0 (3)C11—C10—C9—C8178.4 (2)
O4—Pb1—N1—C19175.51 (18)O6—C11—C10—C9179.8 (2)
O5—Pb1—N1—C156.0 (2)C12—C11—C10—C90.5 (4)
O5—Pb1—N1—C19167.5 (2)O6—C11—C12—C13178.9 (3)
Pb1—O1—C1—O21.3 (2)C10—C11—C12—C130.4 (5)
Pb1—O1—C1—C2179.7 (2)C11—C12—C13—C140.5 (5)
Pb1—O2—C1—O11.6 (3)C12—C13—C14—C90.3 (5)
Pb1—O2—C1—C2179.40 (18)C17—C16—C15—N11.4 (4)
Pb1—O4—C8—O50.2 (2)C18—C17—C16—C150.5 (4)
Pb1—O4—C8—C9179.1 (2)C20—C17—C16—C15179.4 (3)
Pb1—O5—C8—O40.3 (3)C16—C17—C18—C190.3 (4)
Pb1—O5—C8—C9179.06 (19)C20—C17—C18—C19179.8 (3)
Pb1—N1—C15—C16172.0 (2)C16—C17—C20—O7178.6 (3)
C19—N1—C15—C161.5 (4)C16—C17—C20—N21.9 (4)
Pb1—N1—C19—C18173.3 (2)C18—C17—C20—O71.5 (4)
C15—N1—C19—C180.7 (4)C18—C17—C20—N2177.9 (3)
O1—C1—C2—C3178.9 (2)N1—C19—C18—C170.2 (4)
Symmetry codes: (i) x1, y, z; (ii) x, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O4iii0.84 (4)2.21 (4)3.046 (3)175 (4)
N2—H22···O8iv0.85 (4)2.06 (4)2.880 (5)162 (4)
O3—H31···O7v0.86 (5)1.81 (5)2.646 (3)166 (4)
O6—H61···O1vi0.73 (6)2.05 (6)2.755 (4)161 (6)
O8—H81···O6vii0.89 (4)2.02 (4)2.846 (3)154 (4)
O8—H82···O2viii0.87 (5)2.31 (5)3.018 (3)139 (5)
O8—H82···O3ix0.87 (5)2.44 (6)3.054 (3)128 (4)
C12—H12···O1vi0.932.573.269 (4)132
C15—H15···O50.932.463.060 (4)122
C16—H16···O8iv0.932.513.413 (4)165
Symmetry codes: (iii) x+1, y, z1; (iv) x+1, y+1, z1; (v) x, y, z+1; (vi) x, y+1, z; (vii) x, y1, z; (viii) x, y+1, z+1; (ix) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Pb(C7H5O3)2(C6H6N2O)]·H2O
Mr621.56
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.3626 (2), 12.1382 (3), 12.1789 (3)
α, β, γ (°)67.165 (2), 74.192 (3), 88.921 (3)
V3)960.53 (5)
Z2
Radiation typeMo Kα
µ (mm1)8.84
Crystal size (mm)0.26 × 0.14 × 0.13
Data collection
DiffractometerBruker Kappa APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.395, 0.603
No. of measured, independent and
observed [I > 2σ(I)] reflections
17040, 4783, 4652
Rint0.032
(sin θ/λ)max1)0.671
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.017, 0.050, 1.19
No. of reflections4783
No. of parameters304
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.94, 1.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Selected bond lengths (Å) top
Pb1—N12.564 (2)Pb1—O42.742 (2)
Pb1—O12.753 (2)Pb1—O52.344 (2)
Pb1—O22.317 (2)Pb1—O5ii2.954 (2)
Pb1—O3i2.899 (2)
Symmetry codes: (i) x1, y, z; (ii) x, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21···O4iii0.84 (4)2.21 (4)3.046 (3)175 (4)
N2—H22···O8iv0.85 (4)2.06 (4)2.880 (5)162 (4)
O3—H31···O7v0.86 (5)1.81 (5)2.646 (3)166 (4)
O6—H61···O1vi0.73 (6)2.05 (6)2.755 (4)161 (6)
O8—H81···O6vii0.89 (4)2.02 (4)2.846 (3)154 (4)
O8—H82···O2viii0.87 (5)2.31 (5)3.018 (3)139 (5)
O8—H82···O3ix0.87 (5)2.44 (6)3.054 (3)128 (4)
C12—H12···O1vi0.932.57003.269 (4)132
C15—H15···O50.932.46003.060 (4)122
C16—H16···O8iv0.932.51003.413 (4)165
Symmetry codes: (iii) x+1, y, z1; (iv) x+1, y+1, z1; (v) x, y, z+1; (vi) x, y+1, z; (vii) x, y1, z; (viii) x, y+1, z+1; (ix) x+1, y+1, z+1.
 

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer.

References

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Volume 68| Part 3| March 2012| Pages m257-m258
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