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

Zaman, İ.G.; Çaylak Delibaş, N.; Necefoğlu, H.; Hökelek, T.

doi:10.1107/S1600536812004357

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

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

doi:10.1107/S1600536812004357

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catena-Poly[[(μ-3-hydroxybenzoato-κ³O¹,O^1′:O³)(μ-3-hydroxybenzoato-κ³O¹,O^1′:O¹)(isonicotinamide-κN¹)lead(II)] monohydrate]

Ibrahim Göker Zaman,^a Nagihan Çaylak Delibaş,^b Hacali Necefoğlu ^a and Tuncer Hökelek ^c ^*

^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 Pb^II 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 Pb^II ion to form polymeric chains along [100], in which the Pb^II 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. π–π 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 ). For N,N-diethylnicotinamide, see: Bigoli et al. (1972 ). For related structures, see: Greenaway et al. (1984 ); Hökelek & Necefoğlu (1996 ); Hökelek, Yılmaz et al. (2009 ); Hökelek, Dal et al. (2009a ,b ,c , 2010 ); Hökelek, Süzen et al. (2010 ); Hökelek et al. (2011 ).

Experimental

Crystal data

[Pb(C₇H₅O₃)₂(C₆H₆N₂O)]·H₂O
M_r = 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 ) T_min = 0.395, T_max = 0.603
17040 measured reflections
4783 independent reflections
4652 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.94 e Å⁻³
Δρ_min = −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	D⋯A	D—H⋯A
N2—H21⋯O4ⁱⁱⁱ	0.84 (4)	2.21 (4)	3.046 (3)	175 (4)
N2—H22⋯O8^iv	0.85 (4)	2.06 (4)	2.880 (5)	162 (4)
O3—H31⋯O7^v	0.86 (5)	1.81 (5)	2.646 (3)	166 (4)
O6—H61⋯O1^vi	0.73 (6)	2.05 (6)	2.755 (4)	161 (6)
O8—H81⋯O6^vii	0.89 (4)	2.02 (4)	2.846 (3)	154 (4)
O8—H82⋯O2^viii	0.87 (5)	2.31 (5)	3.018 (3)	139 (5)
O8—H82⋯O3^ix	0.87 (5)	2.44 (6)	3.054 (3)	128 (4)
C12—H12⋯O1^vi	0.93	2.57	3.269 (4)	132
C15—H15⋯O5	0.93	2.46	3.060 (4)	122
C16—H16⋯O8^iv	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 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812004357/xu5463sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004357/xu5463Isup2.hkl

checkCIF report

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 Pb^II 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 Pb^II ion to form the polymeric complex, in which the Pb^II 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.

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

	Fig. 1. The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The polymeric structure.

catena-Poly[[(µ-3-hydroxybenzoato- κ³O¹,O^1':O³)(µ-3-hydroxybenzoato- κ³O¹,O^1':O¹)(isonicotinamide- κN¹)lead(II)] monohydrate] top

Crystal data top

[Pb(C₇H₅O₃)₂(C₆H₆N₂O)]·H₂O	Z = 2
M_r = 621.56	F(000) = 596
Triclinic, P1	D_x = 2.149 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3626 (2) Å	Cell parameters from 9959 reflections
b = 12.1382 (3) Å	θ = 2.9–28.5°
c = 12.1789 (3) Å	µ = 8.84 mm⁻¹
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 tube	4652 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 28.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.395, T_max = 0.603	k = −16→16
17040 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ²(F_o²) + (0.0228P)² + 0.6812P] where P = (F_o² + 2F_c²)/3
4783 reflections	(Δ/σ)_max = 0.001
304 parameters	Δρ_max = 0.94 e Å⁻³
4 restraints	Δρ_min = −1.27 e Å⁻³

Crystal data top

[Pb(C₇H₅O₃)₂(C₆H₆N₂O)]·H₂O	γ = 88.921 (3)°
M_r = 621.56	V = 960.53 (5) Å³
Triclinic, P1	Z = 2
a = 7.3626 (2) Å	Mo Kα radiation
b = 12.1382 (3) Å	µ = 8.84 mm⁻¹
c = 12.1789 (3) Å	T = 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)
T_min = 0.395, T_max = 0.603	R_int = 0.032
17040 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.017	4 restraints
wR(F²) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	Δρ_max = 0.94 e Å⁻³
4783 reflections	Δρ_min = −1.27 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Pb1	0.030913 (12)	0.835470 (8)	0.138812 (8)	0.00786 (4)
O1	0.1928 (3)	0.62307 (19)	0.21830 (19)	0.0120 (4)
O2	0.2876 (3)	0.79500 (18)	0.21917 (19)	0.0119 (4)
O3	0.8367 (3)	0.7102 (2)	0.40132 (19)	0.0124 (4)
H31	0.765 (6)	0.748 (4)	0.440 (4)	0.024 (10)*
O4	0.0065 (3)	0.98903 (19)	0.25722 (19)	0.0136 (4)
O5	0.1523 (3)	1.03718 (18)	0.05741 (18)	0.0110 (4)
O6	0.0703 (3)	1.3836 (2)	0.3029 (2)	0.0136 (4)
H61	0.111 (7)	1.442 (5)	0.294 (5)	0.042 (15)*
O7	0.6149 (3)	0.7967 (2)	−0.4465 (2)	0.0172 (5)
O8	−0.1509 (3)	0.1982 (2)	0.5265 (2)	0.0168 (4)
H81	−0.066 (6)	0.260 (3)	0.473 (4)	0.057 (16)*
H82	−0.127 (8)	0.204 (5)	0.590 (4)	0.062 (17)*
N1	0.2801 (3)	0.8592 (2)	−0.0646 (2)	0.0106 (5)
N2	0.7553 (4)	0.9791 (3)	−0.4941 (2)	0.0144 (5)
H21	0.830 (5)	0.981 (4)	−0.561 (3)	0.039 (13)*
H22	0.769 (6)	1.035 (3)	−0.471 (4)	0.028 (11)*
C1	0.3015 (4)	0.6828 (3)	0.2424 (2)	0.0088 (5)
C2	0.4561 (4)	0.6274 (2)	0.2976 (2)	0.0090 (5)
C3	0.5721 (4)	0.6960 (3)	0.3251 (2)	0.0093 (5)
H3	0.5529	0.7759	0.3098	0.011*
C4	0.7168 (4)	0.6450 (3)	0.3754 (2)	0.0096 (5)
C5	0.7482 (4)	0.5263 (3)	0.3954 (2)	0.0109 (5)
H5	0.8481	0.4931	0.4262	0.013*
C6	0.6310 (4)	0.4575 (3)	0.3697 (3)	0.0112 (5)
H6	0.6502	0.3775	0.3853	0.013*
C7	0.4846 (4)	0.5077 (3)	0.3203 (2)	0.0096 (5)
H7	0.4063	0.4617	0.3026	0.012*
C8	0.0990 (4)	1.0640 (3)	0.1532 (3)	0.0091 (5)
C9	0.1525 (4)	1.1908 (3)	0.1322 (3)	0.0091 (5)
C10	0.0883 (4)	1.2299 (3)	0.2284 (3)	0.0094 (5)
H10	0.0149	1.1770	0.3063	0.011*
C11	0.1341 (4)	1.3476 (3)	0.2076 (3)	0.0103 (5)
C12	0.2455 (5)	1.4274 (3)	0.0911 (3)	0.0178 (6)
H12	0.2756	1.5067	0.0771	0.021*
C13	0.3106 (5)	1.3867 (3)	−0.0033 (3)	0.0222 (7)
H13	0.3856	1.4392	−0.0808	0.027*
C14	0.2653 (4)	1.2688 (3)	0.0164 (3)	0.0154 (6)
H14	0.3101	1.2422	−0.0473	0.019*
C15	0.4005 (4)	0.9580 (3)	−0.1397 (3)	0.0118 (5)
H15	0.4060	1.0194	−0.1128	0.014*
C16	0.5163 (4)	0.9719 (3)	−0.2555 (3)	0.0118 (5)
H16	0.5959	1.0422	−0.3058	0.014*
C17	0.5126 (4)	0.8796 (3)	−0.2960 (3)	0.0094 (5)
C18	0.3894 (4)	0.7765 (3)	−0.2170 (3)	0.0127 (5)
H18	0.3832	0.7127	−0.2406	0.015*
C19	0.2766 (4)	0.7705 (3)	−0.1032 (3)	0.0116 (5)
H19	0.1946	0.7016	−0.0512	0.014*
C20	0.6331 (4)	0.8831 (3)	−0.4197 (3)	0.0110 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.00963 (6)	0.00600 (6)	0.00604 (6)	−0.00059 (4)	−0.00152 (4)	−0.00083 (4)
O1	0.0153 (9)	0.0070 (10)	0.0142 (10)	−0.0003 (7)	−0.0053 (8)	−0.0041 (8)
O2	0.0148 (9)	0.0063 (10)	0.0158 (10)	0.0004 (7)	−0.0071 (8)	−0.0038 (8)
O3	0.0131 (9)	0.0132 (11)	0.0127 (10)	−0.0004 (8)	−0.0023 (8)	−0.0078 (9)
O4	0.0191 (10)	0.0097 (11)	0.0091 (9)	−0.0018 (8)	−0.0011 (8)	−0.0024 (8)
O5	0.0159 (9)	0.0092 (10)	0.0087 (9)	0.0010 (7)	−0.0028 (7)	−0.0051 (8)
O6	0.0170 (10)	0.0095 (11)	0.0140 (10)	−0.0022 (8)	0.0014 (8)	−0.0082 (9)
O7	0.0193 (10)	0.0158 (12)	0.0166 (11)	−0.0039 (8)	0.0024 (8)	−0.0113 (9)
O8	0.0231 (11)	0.0151 (12)	0.0097 (10)	−0.0060 (9)	−0.0013 (8)	−0.0042 (9)
N1	0.0095 (10)	0.0100 (12)	0.0088 (11)	0.0013 (9)	0.0002 (8)	−0.0019 (9)
N2	0.0185 (12)	0.0136 (13)	0.0096 (12)	−0.0024 (10)	0.0021 (9)	−0.0071 (10)
C1	0.0103 (11)	0.0079 (13)	0.0056 (12)	−0.0003 (9)	0.0005 (9)	−0.0019 (10)
C2	0.0117 (12)	0.0067 (13)	0.0059 (12)	−0.0004 (9)	−0.0002 (9)	−0.0013 (10)
C3	0.0122 (12)	0.0058 (13)	0.0068 (12)	−0.0008 (9)	0.0012 (9)	−0.0017 (10)
C4	0.0101 (12)	0.0117 (14)	0.0047 (11)	−0.0016 (10)	0.0007 (9)	−0.0027 (10)
C5	0.0124 (12)	0.0118 (14)	0.0058 (12)	0.0014 (10)	−0.0003 (9)	−0.0023 (11)
C6	0.0157 (13)	0.0072 (13)	0.0091 (12)	0.0014 (10)	−0.0017 (10)	−0.0027 (11)
C7	0.0121 (12)	0.0075 (13)	0.0083 (12)	−0.0011 (10)	−0.0011 (9)	−0.0033 (10)
C8	0.0087 (11)	0.0084 (13)	0.0094 (12)	0.0001 (9)	−0.0023 (9)	−0.0029 (11)
C9	0.0109 (12)	0.0067 (13)	0.0088 (12)	−0.0001 (9)	−0.0031 (10)	−0.0020 (10)
C10	0.0111 (12)	0.0063 (13)	0.0072 (12)	−0.0012 (10)	−0.0011 (9)	0.0001 (10)
C11	0.0113 (12)	0.0105 (14)	0.0102 (13)	0.0017 (10)	−0.0033 (10)	−0.0051 (11)
C12	0.0259 (15)	0.0104 (15)	0.0129 (14)	−0.0044 (12)	−0.0012 (12)	−0.0030 (12)
C13	0.0323 (17)	0.0158 (17)	0.0103 (14)	−0.0101 (13)	0.0053 (12)	−0.0039 (13)
C14	0.0206 (14)	0.0138 (15)	0.0094 (13)	−0.0041 (11)	−0.0001 (11)	−0.0046 (12)
C15	0.0135 (12)	0.0093 (14)	0.0128 (13)	0.0011 (10)	−0.0022 (10)	−0.0058 (11)
C16	0.0112 (12)	0.0094 (14)	0.0113 (13)	−0.0018 (10)	−0.0002 (10)	−0.0021 (11)
C17	0.0092 (11)	0.0096 (14)	0.0087 (12)	0.0005 (10)	−0.0017 (10)	−0.0033 (11)
C18	0.0132 (12)	0.0109 (14)	0.0145 (14)	0.0007 (10)	−0.0020 (10)	−0.0069 (12)
C19	0.0136 (12)	0.0068 (13)	0.0119 (13)	−0.0019 (10)	−0.0019 (10)	−0.0022 (11)
C20	0.0113 (12)	0.0107 (14)	0.0097 (13)	0.0004 (10)	−0.0014 (10)	−0.0037 (11)

Geometric parameters (Å, º) top

Pb1—N1	2.564 (2)	C5—C4	1.390 (4)
Pb1—O1	2.753 (2)	C5—C6	1.386 (4)
Pb1—O2	2.317 (2)	C5—H5	0.9300
Pb1—O3ⁱ	2.899 (2)	C6—H6	0.9300
Pb1—O4	2.742 (2)	C7—C2	1.393 (4)
Pb1—O5	2.344 (2)	C7—C6	1.393 (4)
Pb1—O5ⁱⁱ	2.954 (2)	C7—H7	0.9300
O1—C1	1.253 (3)	C9—C14	1.390 (4)
O2—C1	1.287 (3)	C8—C9	1.501 (4)
O3—C4	1.370 (3)	C10—C9	1.394 (4)
O3—H31	0.86 (4)	C10—H10	0.9300
O4—C8	1.247 (3)	C11—C10	1.382 (4)
O5—C8	1.288 (3)	C11—C12	1.397 (4)
O6—C11	1.361 (3)	C12—C13	1.389 (4)
O6—H61	0.73 (5)	C12—H12	0.9300
O7—C20	1.234 (4)	C13—C14	1.387 (4)
O8—H81	0.89 (2)	C13—H13	0.9300
O8—H82	0.87 (2)	C14—H14	0.9300
N1—C15	1.344 (4)	C15—H15	0.9300
N1—C19	1.334 (4)	C16—C15	1.382 (4)
N2—C20	1.328 (4)	C16—H16	0.9300
N2—H21	0.844 (19)	C17—C16	1.391 (4)
N2—H22	0.843 (19)	C17—C18	1.396 (4)
C1—C2	1.495 (4)	C17—C20	1.510 (4)
C3—C2	1.390 (4)	C18—H18	0.9300
C3—C4	1.390 (4)	C19—C18	1.383 (4)
C3—H3	0.9300	C19—H19	0.9300

O2—Pb1—O1	51.00 (6)	C2—C7—H7	120.2
O2—Pb1—O4	77.71 (7)	C6—C7—H7	120.2
O2—Pb1—O5	85.33 (7)	O4—C8—O5	121.9 (3)
O2—Pb1—N1	83.32 (7)	O4—C8—C9	121.8 (2)
O4—Pb1—O1	121.06 (6)	O5—C8—C9	116.3 (2)
O5—Pb1—O1	132.63 (6)	C10—C9—C8	120.0 (2)
O5—Pb1—O4	50.94 (6)	C14—C9—C8	119.6 (2)
O5—Pb1—N1	77.24 (7)	C14—C9—C10	120.4 (3)
N1—Pb1—O1	79.96 (7)	C11—C10—C9	119.7 (3)
N1—Pb1—O4	125.57 (7)	C11—C10—H10	120.1
C1—O1—Pb1	83.85 (16)	C9—C10—H10	120.1
C1—O2—Pb1	103.41 (16)	O6—C11—C10	118.7 (3)
C4—O3—H31	105 (3)	O6—C11—C12	120.8 (3)
C8—O4—Pb1	84.76 (16)	C10—C11—C12	120.5 (3)
C8—O5—Pb1	102.42 (17)	C11—C12—H12	120.5
C11—O6—H61	116 (4)	C13—C12—C11	119.1 (3)
H82—O8—H81	92 (5)	C13—C12—H12	120.5
C15—N1—Pb1	124.95 (18)	C12—C13—H13	119.5
C19—N1—Pb1	116.64 (18)	C14—C13—C12	120.9 (3)
C19—N1—C15	118.1 (2)	C14—C13—H13	119.5
C20—N2—H21	120 (3)	C9—C14—H14	120.3
C20—N2—H22	120 (3)	C13—C14—C9	119.3 (3)
H22—N2—H21	119 (4)	C13—C14—H14	120.3
O1—C1—O2	121.7 (2)	N1—C15—C16	122.6 (3)
O1—C1—C2	121.4 (2)	N1—C15—H15	118.7
O2—C1—C2	116.9 (2)	C16—C15—H15	118.7
C3—C2—C1	119.8 (2)	C15—C16—C17	119.3 (3)
C3—C2—C7	120.2 (3)	C15—C16—H16	120.3
C7—C2—C1	120.0 (2)	C17—C16—H16	120.3
C2—C3—H3	120.0	C16—C17—C18	117.9 (2)
C4—C3—C2	120.0 (3)	C16—C17—C20	124.5 (3)
C4—C3—H3	120.0	C18—C17—C20	117.6 (3)
O3—C4—C3	121.7 (3)	C17—C18—H18	120.5
O3—C4—C5	118.3 (2)	C19—C18—C17	119.1 (3)
C3—C4—C5	119.9 (3)	C19—C18—H18	120.5
C4—C5—H5	119.9	N1—C19—C18	123.0 (3)
C6—C5—C4	120.1 (3)	N1—C19—H19	118.5
C6—C5—H5	119.9	C18—C19—H19	118.5
C5—C6—C7	120.2 (3)	O7—C20—N2	123.1 (3)
C5—C6—H6	119.9	O7—C20—C17	118.7 (3)
C7—C6—H6	119.9	N2—C20—C17	118.2 (3)
C2—C7—C6	119.6 (3)

O2—Pb1—O1—C1	0.82 (14)	O1—C1—C2—C7	1.7 (4)
O4—Pb1—O1—C1	−35.34 (17)	O2—C1—C2—C3	2.1 (4)
O5—Pb1—O1—C1	28.21 (18)	O2—C1—C2—C7	−177.3 (2)
N1—Pb1—O1—C1	90.32 (16)	C4—C3—C2—C7	−0.1 (4)
O1—Pb1—O2—C1	−0.81 (14)	C4—C3—C2—C1	−179.5 (2)
O4—Pb1—O2—C1	148.04 (17)	C2—C3—C4—O3	178.6 (2)
O5—Pb1—O2—C1	−160.96 (16)	C2—C3—C4—C5	1.6 (4)
N1—Pb1—O2—C1	−83.29 (16)	C6—C5—C4—O3	−179.6 (2)
O1—Pb1—O4—C8	122.11 (16)	C6—C5—C4—C3	−2.4 (4)
O2—Pb1—O4—C8	94.12 (16)	C4—C5—C6—C7	1.8 (4)
O5—Pb1—O4—C8	0.14 (15)	C6—C7—C2—C1	178.8 (2)
N1—Pb1—O4—C8	21.70 (19)	C6—C7—C2—C3	−0.6 (4)
O1—Pb1—O5—C8	−99.11 (17)	C2—C7—C6—C5	−0.3 (4)
O2—Pb1—O5—C8	−78.09 (16)	O4—C8—C9—C10	−4.2 (4)
O4—Pb1—O5—C8	−0.13 (15)	O4—C8—C9—C14	176.1 (3)
N1—Pb1—O5—C8	−162.28 (17)	O5—C8—C9—C10	175.1 (2)
O1—Pb1—N1—C15	−132.2 (2)	O5—C8—C9—C14	−4.5 (4)
O1—Pb1—N1—C19	54.3 (2)	C8—C9—C14—C13	178.5 (3)
O2—Pb1—N1—C15	−80.7 (2)	C10—C9—C14—C13	−1.2 (5)
O2—Pb1—N1—C19	105.8 (2)	C11—C10—C9—C14	1.3 (4)
O4—Pb1—N1—C15	−11.0 (3)	C11—C10—C9—C8	−178.4 (2)
O4—Pb1—N1—C19	175.51 (18)	O6—C11—C10—C9	−179.8 (2)
O5—Pb1—N1—C15	6.0 (2)	C12—C11—C10—C9	−0.5 (4)
O5—Pb1—N1—C19	−167.5 (2)	O6—C11—C12—C13	178.9 (3)
Pb1—O1—C1—O2	−1.3 (2)	C10—C11—C12—C13	−0.4 (5)
Pb1—O1—C1—C2	179.7 (2)	C11—C12—C13—C14	0.5 (5)
Pb1—O2—C1—O1	1.6 (3)	C12—C13—C14—C9	0.3 (5)
Pb1—O2—C1—C2	−179.40 (18)	C17—C16—C15—N1	−1.4 (4)
Pb1—O4—C8—O5	−0.2 (2)	C18—C17—C16—C15	0.5 (4)
Pb1—O4—C8—C9	179.1 (2)	C20—C17—C16—C15	−179.4 (3)
Pb1—O5—C8—O4	0.3 (3)	C16—C17—C18—C19	0.3 (4)
Pb1—O5—C8—C9	−179.06 (19)	C20—C17—C18—C19	−179.8 (3)
Pb1—N1—C15—C16	−172.0 (2)	C16—C17—C20—O7	−178.6 (3)
C19—N1—C15—C16	1.5 (4)	C16—C17—C20—N2	1.9 (4)
Pb1—N1—C19—C18	173.3 (2)	C18—C17—C20—O7	1.5 (4)
C15—N1—C19—C18	−0.7 (4)	C18—C17—C20—N2	−177.9 (3)
O1—C1—C2—C3	−178.9 (2)	N1—C19—C18—C17	−0.2 (4)

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O4ⁱⁱⁱ	0.84 (4)	2.21 (4)	3.046 (3)	175 (4)
N2—H22···O8^iv	0.85 (4)	2.06 (4)	2.880 (5)	162 (4)
O3—H31···O7^v	0.86 (5)	1.81 (5)	2.646 (3)	166 (4)
O6—H61···O1^vi	0.73 (6)	2.05 (6)	2.755 (4)	161 (6)
O8—H81···O6^vii	0.89 (4)	2.02 (4)	2.846 (3)	154 (4)
O8—H82···O2^viii	0.87 (5)	2.31 (5)	3.018 (3)	139 (5)
O8—H82···O3^ix	0.87 (5)	2.44 (6)	3.054 (3)	128 (4)
C12—H12···O1^vi	0.93	2.57	3.269 (4)	132
C15—H15···O5	0.93	2.46	3.060 (4)	122
C16—H16···O8^iv	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.

Experimental details

Crystal data
Chemical formula	[Pb(C₇H₅O₃)₂(C₆H₆N₂O)]·H₂O
M_r	621.56
Crystal system, space group	Triclinic, 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)
V (Å³)	960.53 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	8.84
Crystal size (mm)	0.26 × 0.14 × 0.13

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.395, 0.603
No. of measured, independent and observed [I > 2σ(I)] reflections	17040, 4783, 4652
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.017, 0.050, 1.19
No. of reflections	4783
No. of parameters	304
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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—N1	2.564 (2)	Pb1—O4	2.742 (2)
Pb1—O1	2.753 (2)	Pb1—O5	2.344 (2)
Pb1—O2	2.317 (2)	Pb1—O5ⁱⁱ	2.954 (2)
Pb1—O3ⁱ	2.899 (2)

Symmetry codes: (i) x−1, y, z; (ii) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O4ⁱⁱⁱ	0.84 (4)	2.21 (4)	3.046 (3)	175 (4)
N2—H22···O8^iv	0.85 (4)	2.06 (4)	2.880 (5)	162 (4)
O3—H31···O7^v	0.86 (5)	1.81 (5)	2.646 (3)	166 (4)
O6—H61···O1^vi	0.73 (6)	2.05 (6)	2.755 (4)	161 (6)
O8—H81···O6^vii	0.89 (4)	2.02 (4)	2.846 (3)	154 (4)
O8—H82···O2^viii	0.87 (5)	2.31 (5)	3.018 (3)	139 (5)
O8—H82···O3^ix	0.87 (5)	2.44 (6)	3.054 (3)	128 (4)
C12—H12···O1^vi	0.93	2.5700	3.269 (4)	132
C15—H15···O5	0.93	2.4600	3.060 (4)	122
C16—H16···O8^iv	0.93	2.5100	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.

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.

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