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In the title complex, [Pb(C14H12N2)(C7H5O3)2]·C14H12N2·3H2O, the PbII ion is coordinated by two N atoms from one 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand and four O atoms from two 3-hydroxy­benzoate anions in a distorted pseudo-square-pyramidal environment, considering the dmphen mol­ecule as an apical ligand. Mol­ecules are linked into a three-dimensional framework through O—H...O and O—H...N hydrogen bonds. The crystal structure is further stabilized by π–π inter­actions between the dmphen rings of neighboring mol­ecules, with a distance between the ring planes of 3.493 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061065/bh2147sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061065/bh2147Isup2.hkl
Contains datablock I

CCDC reference: 672766

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.020
  • wR factor = 0.047
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H4W .. H5W .. 1.46 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.217 0.334 Tmin and Tmax expected: 0.181 0.335 RR = 1.205 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.20 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.55 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C26 - C27 .. 5.06 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pb1 - O1 .. 8.25 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pb1 - O2 .. 9.93 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pb1 - O4 .. 9.31 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pb1 - C1 .. 5.77 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O4 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C25 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 12 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The coordination chemistry of lead(II) with N and O donor ligands has been investigated in the past decade and frequently discussed, as lead is an environmental pollutant with severe toxic effects (Shimoni-Livny et al., 1998; Xuan & Zhao, 2007). The title complex, (I), was recently obtained from the reaction of lead acetate, sodium m-hydroxybenzoate and 2,9-dimethyl-1,10-phenanthroline (dmphen) in an ethanol/water mixture (see Experimental), and its crystal structure is reported here.

Each PbII ion is six-coordinated by two N atoms from a dmphen ligand, and four O atoms from two m-hydroxybenzoate ligands (Fig.1). The four Pb—O bond lengths are different, Pb1—O1 = 2.639 (2), Pb1—O2 = 2.637 (2), Pb1—O4 = 2.569 (2) and Pb1—O5 = 2.6296 (19) Å, respectively. The two Pb—N bond lengths are also different, Pb1—N1 = 2.493 (2) Å and Pb1—N2= 2.477 (2) Å. The PbII ion is located in the center of the basal coordinationplane, and PbO4N2 unit forms a distorted pseudo square-pyramidal environment, considering the dmphen molecule as an apical ligand.

In the crystal structure, molecules are linked into a three dimensional framework by intermolecular O—H···O and O—H···N hydrogen bonds (Fig. 2 and 3). Molecules are also linked into a one dimensional network by ππ interactions between the dmphen ring systems (Fig. 4). These intermolecular interactions occur between the rings within offset face-to-face packing. The distance of neighboring molecules parallel ring planes is 3.493 Å. A three dimensional architecture is thus formed through hydrogen bonds and ππ stacking interactions (Fig. 4).

Related literature top

For related literature, see: Shimoni-Livny et al. (1998); Xuan & Zhao (2007).

Experimental top

A mixture of m-hydroxybenzoic acid (0.070 g, 0.5 mmol) and NaOH (0.018 g, 0.5 mmol) in distilled water (10 ml) was stirred until dissolution, and then Pb(CH3COOH)2.3H2O (0.190 g, 0.5 mmol) was added. A solution of 2,9-dimethyl-1,10-phenanthroline hemihydrate (C14H12N2.0.5H2O, 0.109 g, 0.5 mmol) in ethanol (10 ml) was then added. The mixture was refluxed for 4 h. The hot solution was cooled to room temperature and then filtered. Bright colorless single crystals of (I) appeared over a period of five days by slow evaporation at room temperature.

Refinement top

C-bonded H atoms were placed in calculated positions, with C—H = 0.93 Å (aromatic CH) or C—H = 0.96 Å (methyl CH3), and refined in the riding-model approximation with Uiso(H) = 1.2Ueq(C) for aromatic CH and Uiso(H) = 1.5Ueq(C) otherwise. Hydroxyl and water H atoms were found in a difference map and their coordinates fixed after regularization of geometry. Isotropic displacement parameters were fixed to Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, (I), with atom labels and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The hydrogen-bonding motifs in the crystal structure of (I). Dashed lines indicate the hydrogen bonds.
[Figure 3] Fig. 3. The hydrogen-bonding motifs in the crystal structure of (I), including all molecules. Dashed lines indicate the hydrogen bonds.
[Figure 4] Fig. 4. The ππ stacking and hydrogen bonds in the crystal structure of (I).
(2,9-Dimethyl-1,10-phenanthroline-κ2N,N')bis(3- hydroxybenzoato-κ2O,O')lead(II)–2,9-dimethyl-1,10- phenanthroline–water (1/1/3) top
Crystal data top
[Pb(C14H12N2)(C7H5O3)2]·C14H12N2·3H2OF(000) = 3792
Mr = 951.97Dx = 1.616 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6283 reflections
a = 31.662 (3) Åθ = 2.4–27.0°
b = 10.8291 (10) ŵ = 4.37 mm1
c = 27.381 (4) ÅT = 291 K
β = 123.530 (1)°Block, colourless
V = 7825.9 (15) Å30.41 × 0.35 × 0.25 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
7287 independent reflections
Radiation source: fine-focus sealed tube6143 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ϕ and ω scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 3738
Tmin = 0.217, Tmax = 0.334k = 1313
28443 measured reflectionsl = 3233
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)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0222P)2 + 6.8596P]
where P = (Fo2 + 2Fc2)/3
7287 reflections(Δ/σ)max = 0.003
511 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.49 e Å3
Crystal data top
[Pb(C14H12N2)(C7H5O3)2]·C14H12N2·3H2OV = 7825.9 (15) Å3
Mr = 951.97Z = 8
Monoclinic, C2/cMo Kα radiation
a = 31.662 (3) ŵ = 4.37 mm1
b = 10.8291 (10) ÅT = 291 K
c = 27.381 (4) Å0.41 × 0.35 × 0.25 mm
β = 123.530 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
7287 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
6143 reflections with I > 2σ(I)
Tmin = 0.217, Tmax = 0.334Rint = 0.022
28443 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0200 restraints
wR(F2) = 0.047H-atom parameters constrained
S = 1.03Δρmax = 0.45 e Å3
7287 reflectionsΔρmin = 0.49 e Å3
511 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pb10.224379 (4)0.879582 (10)0.373487 (4)0.04096 (4)
O10.29906 (8)0.7989 (2)0.47679 (9)0.0708 (7)
O20.26753 (9)0.9783 (2)0.47864 (9)0.0709 (6)
O30.38864 (13)1.1174 (3)0.68961 (11)0.0961 (9)
H30.38251.17500.66720.144*
O40.14958 (7)1.02393 (19)0.30704 (9)0.0565 (5)
O50.15723 (7)0.87141 (19)0.25972 (8)0.0532 (5)
O60.02455 (8)0.8054 (3)0.08300 (11)0.0905 (9)
H60.00490.75160.08640.136*
O70.36781 (9)0.6228 (2)0.49854 (11)0.0779 (7)
H1W0.34770.68110.49010.117*
H2W0.39700.64290.52590.117*
O80.37422 (9)0.3244 (3)0.62932 (12)0.0858 (8)
H3W0.36700.37040.64880.129*
H4W0.35350.34540.59500.129*
O90.18511 (11)0.0677 (3)0.48323 (13)0.1003 (9)
H5W0.16380.05500.44780.150*
H6W0.21040.02270.49560.150*
N10.27666 (8)0.7787 (2)0.34240 (9)0.0445 (5)
N20.27281 (7)1.0306 (2)0.35509 (9)0.0386 (5)
N30.05922 (9)0.7416 (3)0.05994 (11)0.0587 (7)
N40.02519 (8)0.5671 (2)0.10211 (10)0.0507 (6)
C10.29728 (11)0.8896 (3)0.50406 (13)0.0522 (7)
C20.33241 (11)0.8923 (3)0.56993 (12)0.0506 (7)
C30.35607 (12)0.7845 (3)0.60090 (13)0.0601 (8)
H3A0.35040.70990.58130.072*
C40.38851 (13)0.7905 (4)0.66183 (15)0.0739 (11)
H40.40400.71900.68320.089*
C50.39779 (14)0.9014 (4)0.69050 (15)0.0765 (12)
H50.41900.90390.73120.092*
C60.37589 (13)1.0092 (4)0.65958 (15)0.0689 (10)
C70.34198 (11)1.0042 (3)0.59884 (13)0.0571 (8)
H70.32591.07560.57780.069*
C80.24701 (13)1.2019 (3)0.39162 (16)0.0654 (9)
H8A0.21321.22760.36190.098*
H8B0.26581.27130.41580.098*
H8C0.24561.13880.41530.098*
C90.27266 (10)1.1519 (2)0.36334 (13)0.0479 (7)
C100.29607 (12)1.2343 (3)0.34563 (15)0.0656 (9)
H100.29571.31850.35210.079*
C110.31891 (13)1.1934 (4)0.31954 (15)0.0699 (10)
H110.33381.24900.30750.084*
C120.32017 (11)1.0657 (3)0.31043 (12)0.0557 (8)
C130.34404 (13)1.0145 (5)0.28337 (15)0.0770 (12)
H130.35921.06700.27050.092*
C140.34495 (13)0.8918 (5)0.27618 (15)0.0797 (13)
H140.36030.86090.25790.096*
C150.32265 (11)0.8086 (4)0.29622 (13)0.0618 (9)
C160.32383 (15)0.6795 (5)0.29173 (16)0.0848 (13)
H160.33920.64470.27420.102*
C170.30295 (17)0.6053 (4)0.31249 (18)0.0862 (13)
H170.30420.52010.30940.103*
C180.27932 (13)0.6565 (3)0.33871 (14)0.0622 (9)
C190.25614 (17)0.5778 (3)0.36306 (17)0.0871 (13)
H19A0.28160.55610.40280.131*
H19B0.24250.50410.34000.131*
H19C0.22950.62290.36190.131*
C200.29834 (10)0.8550 (3)0.32251 (11)0.0440 (7)
C210.29668 (9)0.9861 (3)0.32931 (11)0.0413 (6)
C220.06912 (18)0.9596 (4)0.0499 (2)0.1226 (19)
H22A0.05020.96360.06780.184*
H22B0.05111.00290.01320.184*
H22C0.10170.99700.07540.184*
C230.07584 (13)0.8271 (4)0.03950 (17)0.0797 (11)
C240.10013 (16)0.7940 (6)0.0111 (2)0.1032 (17)
H240.11110.85520.00320.124*
C250.10757 (16)0.6739 (7)0.00463 (19)0.1022 (17)
H250.12360.65270.01420.123*
C260.09143 (12)0.5823 (4)0.02599 (14)0.0699 (10)
C270.09865 (15)0.4532 (6)0.02211 (17)0.0940 (16)
H270.11470.42750.00380.113*
C280.08299 (16)0.3691 (5)0.04407 (19)0.0915 (15)
H280.08880.28600.04140.110*
C290.05769 (12)0.4029 (3)0.07143 (15)0.0629 (9)
C300.04061 (15)0.3174 (4)0.09526 (19)0.0881 (14)
H300.04530.23340.09300.106*
C310.01745 (16)0.3562 (4)0.1214 (2)0.0929 (15)
H310.00650.29930.13760.112*
C320.00986 (12)0.4827 (4)0.12410 (15)0.0694 (10)
C330.01798 (15)0.5277 (5)0.15087 (18)0.1048 (16)
H33A0.00530.60740.16820.157*
H33B0.01290.47060.18050.157*
H33C0.05350.53380.12100.157*
C340.04918 (10)0.5289 (3)0.07621 (12)0.0483 (7)
C350.06661 (10)0.6209 (3)0.05336 (12)0.0523 (7)
C360.13066 (10)0.9517 (2)0.26357 (11)0.0392 (6)
C370.07541 (10)0.9626 (2)0.21688 (11)0.0390 (6)
C380.04679 (11)1.0572 (3)0.21906 (13)0.0519 (7)
H380.06221.11560.24890.062*
C390.00465 (12)1.0644 (3)0.17683 (14)0.0596 (8)
H390.02381.12730.17860.071*
C400.02758 (11)0.9795 (3)0.13249 (14)0.0589 (8)
H400.06220.98490.10440.071*
C410.00033 (11)0.8858 (3)0.12926 (14)0.0573 (8)
C420.05214 (10)0.8775 (3)0.17154 (12)0.0497 (7)
H420.07110.81480.16930.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.03378 (6)0.05033 (7)0.03576 (6)0.00360 (5)0.01731 (5)0.00157 (5)
O10.0534 (13)0.0931 (18)0.0474 (13)0.0185 (12)0.0163 (11)0.0101 (12)
O20.0758 (16)0.0763 (16)0.0482 (13)0.0180 (14)0.0264 (12)0.0043 (12)
O30.105 (2)0.125 (3)0.0602 (16)0.017 (2)0.0464 (17)0.0352 (16)
O40.0442 (11)0.0573 (13)0.0520 (12)0.0007 (10)0.0165 (10)0.0189 (10)
O50.0401 (10)0.0676 (14)0.0426 (11)0.0102 (10)0.0170 (9)0.0114 (10)
O60.0435 (13)0.101 (2)0.0773 (17)0.0139 (13)0.0020 (12)0.0476 (15)
O70.0653 (15)0.0707 (16)0.0834 (17)0.0128 (12)0.0319 (14)0.0016 (13)
O80.0697 (16)0.0994 (19)0.0879 (19)0.0021 (15)0.0433 (15)0.0342 (16)
O90.097 (2)0.108 (2)0.105 (2)0.0183 (18)0.0613 (19)0.0024 (18)
N10.0465 (13)0.0411 (13)0.0351 (12)0.0026 (11)0.0157 (11)0.0009 (10)
N20.0328 (11)0.0392 (12)0.0395 (12)0.0002 (9)0.0173 (10)0.0029 (10)
N30.0425 (14)0.0665 (18)0.0574 (16)0.0041 (13)0.0214 (13)0.0051 (14)
N40.0359 (13)0.0639 (16)0.0456 (14)0.0023 (12)0.0182 (12)0.0017 (12)
C10.0418 (16)0.071 (2)0.0460 (17)0.0045 (16)0.0254 (14)0.0047 (16)
C20.0410 (15)0.075 (2)0.0394 (15)0.0063 (15)0.0244 (13)0.0013 (15)
C30.059 (2)0.076 (2)0.0487 (18)0.0096 (17)0.0317 (16)0.0072 (16)
C40.062 (2)0.105 (3)0.054 (2)0.006 (2)0.0318 (18)0.022 (2)
C50.059 (2)0.128 (4)0.0382 (18)0.016 (2)0.0243 (17)0.002 (2)
C60.061 (2)0.108 (3)0.050 (2)0.013 (2)0.0379 (18)0.013 (2)
C70.0515 (18)0.084 (2)0.0435 (17)0.0019 (17)0.0309 (15)0.0026 (16)
C80.064 (2)0.0451 (18)0.083 (2)0.0014 (16)0.0382 (19)0.0140 (17)
C90.0381 (15)0.0383 (16)0.0536 (17)0.0010 (12)0.0167 (14)0.0022 (13)
C100.056 (2)0.0467 (19)0.080 (2)0.0059 (15)0.0290 (19)0.0172 (17)
C110.053 (2)0.074 (3)0.070 (2)0.0105 (17)0.0257 (18)0.0306 (19)
C120.0381 (16)0.085 (2)0.0373 (16)0.0023 (15)0.0166 (14)0.0156 (16)
C130.0469 (19)0.142 (4)0.046 (2)0.004 (2)0.0281 (17)0.018 (2)
C140.049 (2)0.151 (4)0.0439 (19)0.015 (2)0.0286 (17)0.002 (2)
C150.0424 (17)0.099 (3)0.0357 (16)0.0159 (17)0.0165 (14)0.0070 (17)
C160.068 (2)0.112 (4)0.057 (2)0.034 (2)0.023 (2)0.024 (2)
C170.089 (3)0.064 (3)0.074 (3)0.027 (2)0.025 (2)0.015 (2)
C180.063 (2)0.0459 (18)0.0468 (18)0.0084 (15)0.0113 (16)0.0071 (14)
C190.113 (3)0.0406 (18)0.081 (3)0.010 (2)0.037 (3)0.0009 (18)
C200.0314 (13)0.0614 (19)0.0289 (13)0.0072 (13)0.0102 (11)0.0007 (12)
C210.0323 (14)0.0541 (17)0.0315 (14)0.0021 (12)0.0138 (12)0.0055 (12)
C220.097 (3)0.086 (3)0.147 (5)0.016 (3)0.043 (3)0.031 (3)
C230.048 (2)0.091 (3)0.074 (3)0.0106 (19)0.0175 (19)0.020 (2)
C240.065 (3)0.160 (5)0.079 (3)0.024 (3)0.036 (2)0.034 (3)
C250.058 (2)0.191 (6)0.064 (3)0.009 (3)0.038 (2)0.007 (3)
C260.0425 (18)0.117 (3)0.0456 (19)0.0036 (19)0.0214 (16)0.0049 (19)
C270.054 (2)0.157 (5)0.058 (2)0.027 (3)0.022 (2)0.030 (3)
C280.065 (3)0.101 (3)0.071 (3)0.026 (2)0.014 (2)0.031 (3)
C290.0454 (18)0.059 (2)0.0537 (19)0.0055 (15)0.0082 (16)0.0132 (16)
C300.065 (3)0.054 (2)0.087 (3)0.005 (2)0.006 (2)0.001 (2)
C310.062 (3)0.090 (3)0.090 (3)0.015 (2)0.019 (2)0.028 (3)
C320.0415 (18)0.096 (3)0.058 (2)0.0078 (18)0.0194 (16)0.012 (2)
C330.065 (3)0.177 (5)0.083 (3)0.007 (3)0.048 (2)0.020 (3)
C340.0336 (15)0.0576 (18)0.0386 (15)0.0002 (13)0.0105 (13)0.0070 (13)
C350.0313 (14)0.076 (2)0.0391 (15)0.0004 (15)0.0128 (12)0.0060 (15)
C360.0386 (14)0.0427 (16)0.0359 (14)0.0011 (12)0.0203 (12)0.0009 (12)
C370.0381 (14)0.0429 (15)0.0357 (14)0.0037 (12)0.0203 (12)0.0017 (12)
C380.0492 (17)0.0523 (18)0.0458 (17)0.0066 (14)0.0208 (15)0.0102 (14)
C390.0502 (18)0.063 (2)0.060 (2)0.0179 (16)0.0267 (16)0.0034 (17)
C400.0373 (16)0.074 (2)0.0525 (19)0.0135 (15)0.0164 (14)0.0033 (16)
C410.0411 (16)0.067 (2)0.0488 (17)0.0041 (15)0.0152 (14)0.0138 (16)
C420.0391 (15)0.0549 (18)0.0475 (16)0.0095 (13)0.0192 (13)0.0084 (14)
Geometric parameters (Å, º) top
Pb1—N12.493 (2)C13—H130.9300
Pb1—N22.477 (2)C14—C151.428 (5)
Pb1—O12.639 (2)C14—H140.9300
Pb1—O22.637 (2)C15—C201.405 (4)
Pb1—O42.569 (2)C15—C161.406 (6)
Pb1—O52.6296 (19)C16—C171.349 (6)
O1—C11.254 (4)C16—H160.9300
O2—C11.253 (4)C17—C181.406 (6)
O3—C61.359 (4)C17—H170.9300
O3—H30.8200C18—C191.500 (5)
O4—C361.265 (3)C19—H19A0.9600
O5—C361.254 (3)C19—H19B0.9600
O6—C411.371 (4)C19—H19C0.9600
O6—H60.8200C20—C211.437 (4)
O7—H1W0.8331C22—C231.501 (6)
O7—H2W0.8357C22—H22A0.9600
O8—H3W0.8493C22—H22B0.9600
O8—H4W0.8274C22—H22C0.9600
O9—H5W0.8310C23—C241.409 (6)
O9—H6W0.8336C24—C251.351 (7)
N1—C181.334 (4)C24—H240.9300
N1—C201.365 (4)C25—C261.385 (7)
N2—C91.333 (3)C25—H250.9300
N2—C211.375 (3)C26—C351.416 (5)
N3—C231.331 (4)C26—C271.430 (6)
N3—C351.357 (4)C27—C281.329 (6)
N4—C321.325 (4)C27—H270.9300
N4—C341.359 (4)C28—C291.414 (6)
C1—C21.508 (4)C28—H280.9300
C2—C71.386 (4)C29—C301.401 (6)
C2—C31.393 (4)C29—C341.411 (4)
C3—C41.396 (4)C30—C311.344 (6)
C3—H3A0.9300C30—H300.9300
C4—C51.375 (5)C31—C321.400 (6)
C4—H40.9300C31—H310.9300
C5—C61.383 (5)C32—C331.505 (5)
C5—H50.9300C33—H33A0.9600
C6—C71.396 (4)C33—H33B0.9600
C7—H70.9300C33—H33C0.9600
C8—C91.499 (4)C34—C351.438 (4)
C8—H8A0.9600C36—C371.496 (3)
C8—H8B0.9600C37—C421.387 (4)
C8—H8C0.9600C37—C381.390 (4)
C9—C101.406 (4)C38—C391.384 (4)
C10—C111.342 (5)C38—H380.9300
C10—H100.9300C39—C401.369 (4)
C11—C121.410 (5)C39—H390.9300
C11—H110.9300C40—C411.379 (4)
C12—C211.410 (4)C40—H400.9300
C12—C131.431 (5)C41—C421.393 (4)
C13—C141.346 (5)C42—H420.9300
N2—Pb1—N167.50 (7)C18—C17—H17119.9
N2—Pb1—O483.47 (7)N1—C18—C17120.2 (4)
N1—Pb1—O4123.42 (7)N1—C18—C19117.6 (3)
N2—Pb1—O588.14 (7)C17—C18—C19122.2 (3)
N1—Pb1—O580.54 (6)C18—C19—H19A109.5
O4—Pb1—O549.89 (6)C18—C19—H19B109.5
N2—Pb1—O287.06 (7)H19A—C19—H19B109.5
N1—Pb1—O2120.61 (7)C18—C19—H19C109.5
O4—Pb1—O2104.22 (7)H19A—C19—H19C109.5
O5—Pb1—O2154.07 (7)H19B—C19—H19C109.5
N2—Pb1—O198.49 (7)N1—C20—C15121.8 (3)
N1—Pb1—O181.39 (7)N1—C20—C21118.9 (2)
O4—Pb1—O1152.86 (7)C15—C20—C21119.3 (3)
O5—Pb1—O1156.62 (7)N2—C21—C12121.7 (3)
O2—Pb1—O149.22 (7)N2—C21—C20118.9 (2)
C1—O1—Pb194.05 (18)C12—C21—C20119.5 (3)
C1—O2—Pb194.19 (19)C23—C22—H22A109.5
C6—O3—H3109.5C23—C22—H22B109.5
C36—O4—Pb193.58 (16)H22A—C22—H22B109.5
C36—O5—Pb191.03 (15)C23—C22—H22C109.5
C41—O6—H6109.5H22A—C22—H22C109.5
H1W—O7—H2W110.4H22B—C22—H22C109.5
H3W—O8—H4W103.4N3—C23—C24121.2 (4)
H5W—O9—H6W110.8N3—C23—C22117.0 (4)
C18—N1—C20120.3 (3)C24—C23—C22121.7 (4)
C18—N1—Pb1122.8 (2)C25—C24—C23120.3 (4)
C20—N1—Pb1116.50 (17)C25—C24—H24119.8
C9—N2—C21119.1 (2)C23—C24—H24119.8
C9—N2—Pb1123.75 (18)C24—C25—C26120.2 (4)
C21—N2—Pb1116.78 (17)C24—C25—H25119.9
C23—N3—C35118.5 (3)C26—C25—H25119.9
C32—N4—C34118.6 (3)C25—C26—C35117.0 (4)
O2—C1—O1122.5 (3)C25—C26—C27123.9 (4)
O2—C1—C2118.8 (3)C35—C26—C27119.1 (4)
O1—C1—C2118.8 (3)C28—C27—C26121.4 (4)
C7—C2—C3120.7 (3)C28—C27—H27119.3
C7—C2—C1118.9 (3)C26—C27—H27119.3
C3—C2—C1120.4 (3)C27—C28—C29121.6 (4)
C2—C3—C4118.8 (3)C27—C28—H28119.2
C2—C3—H3A120.6C29—C28—H28119.2
C4—C3—H3A120.6C30—C29—C34116.9 (4)
C5—C4—C3120.5 (4)C30—C29—C28123.6 (4)
C5—C4—H4119.8C34—C29—C28119.5 (4)
C3—C4—H4119.8C31—C30—C29120.4 (4)
C4—C5—C6120.7 (3)C31—C30—H30119.8
C4—C5—H5119.6C29—C30—H30119.8
C6—C5—H5119.6C30—C31—C32119.6 (4)
O3—C6—C5118.5 (3)C30—C31—H31120.2
O3—C6—C7122.1 (4)C32—C31—H31120.2
C5—C6—C7119.5 (4)N4—C32—C31122.3 (4)
C2—C7—C6119.8 (3)N4—C32—C33117.3 (4)
C2—C7—H7120.1C31—C32—C33120.4 (4)
C6—C7—H7120.1C32—C33—H33A109.5
C9—C8—H8A109.5C32—C33—H33B109.5
C9—C8—H8B109.5H33A—C33—H33B109.5
H8A—C8—H8B109.5C32—C33—H33C109.5
C9—C8—H8C109.5H33A—C33—H33C109.5
H8A—C8—H8C109.5H33B—C33—H33C109.5
H8B—C8—H8C109.5N4—C34—C29122.2 (3)
N2—C9—C10121.0 (3)N4—C34—C35118.4 (3)
N2—C9—C8119.8 (3)C29—C34—C35119.4 (3)
C10—C9—C8119.2 (3)N3—C35—C26122.8 (3)
C11—C10—C9121.1 (3)N3—C35—C34118.3 (3)
C11—C10—H10119.5C26—C35—C34119.0 (3)
C9—C10—H10119.5O5—C36—O4121.1 (2)
C10—C11—C12119.6 (3)O5—C36—C37120.3 (2)
C10—C11—H11120.2O4—C36—C37118.6 (2)
C12—C11—H11120.2C42—C37—C38119.4 (2)
C11—C12—C21117.5 (3)C42—C37—C36120.3 (2)
C11—C12—C13123.1 (3)C38—C37—C36120.2 (2)
C21—C12—C13119.3 (3)C39—C38—C37120.0 (3)
C14—C13—C12121.2 (4)C39—C38—H38120.0
C14—C13—H13119.4C37—C38—H38120.0
C12—C13—H13119.4C40—C39—C38120.4 (3)
C13—C14—C15120.8 (3)C40—C39—H39119.8
C13—C14—H14119.6C38—C39—H39119.8
C15—C14—H14119.6C39—C40—C41120.4 (3)
C20—C15—C16116.7 (4)C39—C40—H40119.8
C20—C15—C14119.9 (3)C41—C40—H40119.8
C16—C15—C14123.4 (4)O6—C41—C40117.7 (3)
C17—C16—C15120.8 (4)O6—C41—C42122.5 (3)
C17—C16—H16119.6C40—C41—C42119.8 (3)
C15—C16—H16119.6C37—C42—C41120.0 (3)
C16—C17—C18120.3 (4)C37—C42—H42120.0
C16—C17—H17119.9C41—C42—H42120.0
N2—Pb1—O1—C180.06 (19)C20—N1—C18—C19178.1 (3)
N1—Pb1—O1—C1145.6 (2)Pb1—N1—C18—C199.5 (4)
O4—Pb1—O1—C112.2 (3)C16—C17—C18—N11.1 (5)
O5—Pb1—O1—C1174.70 (17)C16—C17—C18—C19179.2 (4)
O2—Pb1—O1—C11.44 (17)C18—N1—C20—C151.9 (4)
N2—Pb1—O2—C1105.30 (19)Pb1—N1—C20—C15170.99 (19)
N1—Pb1—O2—C143.7 (2)C18—N1—C20—C21177.4 (2)
O4—Pb1—O2—C1172.20 (18)Pb1—N1—C20—C219.7 (3)
O5—Pb1—O2—C1175.06 (17)C16—C15—C20—N10.4 (4)
O1—Pb1—O2—C11.44 (17)C14—C15—C20—N1179.8 (3)
N2—Pb1—O4—C36104.53 (17)C16—C15—C20—C21178.9 (3)
N1—Pb1—O4—C3647.02 (18)C14—C15—C20—C210.6 (4)
O5—Pb1—O4—C3611.45 (15)C9—N2—C21—C121.2 (4)
O2—Pb1—O4—C36170.18 (16)Pb1—N2—C21—C12172.30 (19)
O1—Pb1—O4—C36159.58 (17)C9—N2—C21—C20177.7 (2)
N2—Pb1—O5—C3694.55 (17)Pb1—N2—C21—C208.8 (3)
N1—Pb1—O5—C36162.04 (17)C11—C12—C21—N20.7 (4)
O4—Pb1—O5—C3611.52 (15)C13—C12—C21—N2179.4 (3)
O2—Pb1—O5—C3615.1 (3)C11—C12—C21—C20178.2 (2)
O1—Pb1—O5—C36158.15 (18)C13—C12—C21—C201.7 (4)
N2—Pb1—N1—C18177.4 (2)N1—C20—C21—N20.7 (3)
O4—Pb1—N1—C18117.5 (2)C15—C20—C21—N2180.0 (2)
O5—Pb1—N1—C1890.7 (2)N1—C20—C21—C12178.2 (2)
O2—Pb1—N1—C18105.4 (2)C15—C20—C21—C121.1 (4)
O1—Pb1—N1—C1874.4 (2)C35—N3—C23—C240.6 (5)
N2—Pb1—N1—C209.94 (16)C35—N3—C23—C22177.3 (3)
O4—Pb1—N1—C2055.17 (19)N3—C23—C24—C250.7 (6)
O5—Pb1—N1—C2081.98 (17)C22—C23—C24—C25177.1 (4)
O2—Pb1—N1—C2081.91 (18)C23—C24—C25—C260.1 (7)
O1—Pb1—N1—C20112.91 (18)C24—C25—C26—C351.0 (6)
N1—Pb1—N2—C9177.3 (2)C24—C25—C26—C27178.7 (4)
O4—Pb1—N2—C952.4 (2)C25—C26—C27—C28179.1 (4)
O5—Pb1—N2—C9102.2 (2)C35—C26—C27—C280.6 (6)
O2—Pb1—N2—C952.3 (2)C26—C27—C28—C291.1 (6)
O1—Pb1—N2—C9100.3 (2)C27—C28—C29—C30179.9 (4)
N1—Pb1—N2—C219.58 (16)C27—C28—C29—C340.7 (5)
O4—Pb1—N2—C21120.78 (17)C34—C29—C30—C310.2 (5)
O5—Pb1—N2—C2170.95 (17)C28—C29—C30—C31179.0 (4)
O2—Pb1—N2—C21134.55 (17)C29—C30—C31—C320.8 (6)
O1—Pb1—N2—C2186.53 (17)C34—N4—C32—C310.1 (5)
Pb1—O2—C1—O12.7 (3)C34—N4—C32—C33178.2 (3)
Pb1—O2—C1—C2177.5 (2)C30—C31—C32—N40.6 (6)
Pb1—O1—C1—O22.7 (3)C30—C31—C32—C33177.4 (4)
Pb1—O1—C1—C2177.5 (2)C32—N4—C34—C290.8 (4)
O2—C1—C2—C719.0 (4)C32—N4—C34—C35178.9 (3)
O1—C1—C2—C7160.8 (3)C30—C29—C34—N40.6 (4)
O2—C1—C2—C3163.1 (3)C28—C29—C34—N4179.9 (3)
O1—C1—C2—C317.1 (4)C30—C29—C34—C35179.0 (3)
C7—C2—C3—C41.8 (5)C28—C29—C34—C350.3 (4)
C1—C2—C3—C4179.7 (3)C23—N3—C35—C260.3 (4)
C2—C3—C4—C51.5 (5)C23—N3—C35—C34179.2 (3)
C3—C4—C5—C61.1 (5)C25—C26—C35—N31.2 (5)
C4—C5—C6—O3176.1 (3)C27—C26—C35—N3178.6 (3)
C4—C5—C6—C73.3 (5)C25—C26—C35—C34180.0 (3)
C3—C2—C7—C60.4 (5)C27—C26—C35—C340.3 (4)
C1—C2—C7—C6177.6 (3)N4—C34—C35—N31.4 (4)
O3—C6—C7—C2176.4 (3)C29—C34—C35—N3178.2 (3)
C5—C6—C7—C22.9 (5)N4—C34—C35—C26179.7 (3)
C21—N2—C9—C100.6 (4)C29—C34—C35—C260.7 (4)
Pb1—N2—C9—C10172.4 (2)Pb1—O5—C36—O421.3 (3)
C21—N2—C9—C8179.7 (3)Pb1—O5—C36—C37157.8 (2)
Pb1—N2—C9—C87.3 (4)Pb1—O4—C36—O521.8 (3)
N2—C9—C10—C110.5 (5)Pb1—O4—C36—C37157.3 (2)
C8—C9—C10—C11179.2 (3)O5—C36—C37—C425.5 (4)
C9—C10—C11—C120.9 (5)O4—C36—C37—C42173.6 (3)
C10—C11—C12—C210.3 (4)O5—C36—C37—C38175.4 (3)
C10—C11—C12—C13179.5 (3)O4—C36—C37—C385.5 (4)
C11—C12—C13—C14179.1 (3)C42—C37—C38—C391.3 (5)
C21—C12—C13—C140.7 (5)C36—C37—C38—C39177.8 (3)
C12—C13—C14—C150.9 (5)C37—C38—C39—C400.6 (5)
C13—C14—C15—C201.6 (5)C38—C39—C40—C410.2 (5)
C13—C14—C15—C16177.8 (3)C39—C40—C41—O6178.4 (3)
C20—C15—C16—C170.7 (5)C39—C40—C41—C420.2 (5)
C14—C15—C16—C17178.7 (3)C38—C37—C42—C411.2 (4)
C15—C16—C17—C180.4 (6)C36—C37—C42—C41177.9 (3)
C20—N1—C18—C172.2 (4)O6—C41—C42—C37179.0 (3)
Pb1—N1—C18—C17170.2 (2)C40—C41—C42—C370.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O8i0.821.862.669 (4)169
O6—H6···N40.822.152.916 (4)155
O7—H1W···O10.831.882.702 (3)172
O7—H2W···O6ii0.842.152.977 (3)169
O8—H3W···O4iii0.851.942.784 (3)180
O8—H4W···O9iv0.832.022.828 (4)166
O9—H6W···O2v0.832.152.850 (4)141
O9—H5W···O8iv0.832.192.828 (4)133
O6—H6···N30.822.513.124 (4)133
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+3/2, z+1/2; (iii) x+1/2, y+3/2, z+1; (iv) x+1/2, y+1/2, z+1; (v) x, y1, z.

Experimental details

Crystal data
Chemical formula[Pb(C14H12N2)(C7H5O3)2]·C14H12N2·3H2O
Mr951.97
Crystal system, space groupMonoclinic, C2/c
Temperature (K)291
a, b, c (Å)31.662 (3), 10.8291 (10), 27.381 (4)
β (°) 123.530 (1)
V3)7825.9 (15)
Z8
Radiation typeMo Kα
µ (mm1)4.37
Crystal size (mm)0.41 × 0.35 × 0.25
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.217, 0.334
No. of measured, independent and
observed [I > 2σ(I)] reflections
28443, 7287, 6143
Rint0.022
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.020, 0.047, 1.03
No. of reflections7287
No. of parameters511
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.45, 0.49

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Selected bond lengths (Å) top
Pb1—N12.493 (2)Pb1—O22.637 (2)
Pb1—N22.477 (2)Pb1—O42.569 (2)
Pb1—O12.639 (2)Pb1—O52.6296 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O8i0.821.862.669 (4)168.8
O6—H6···N40.822.152.916 (4)155.2
O7—H1W···O10.831.882.702 (3)171.6
O7—H2W···O6ii0.842.152.977 (3)168.6
O8—H3W···O4iii0.851.942.784 (3)179.6
O8—H4W···O9iv0.832.022.828 (4)165.7
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+3/2, z+1/2; (iii) x+1/2, y+3/2, z+1; (iv) x+1/2, y+1/2, z+1.
 

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