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Aroylhydrazones of ortho-hy­droxy aldehydes are Schiff base ligands that typically coordinate as a chelate in an O,N,O′-manner. Dinuclear complexes are normally observed, with the phenolate O atom acting as the bridging atom. The switchable protonation state of the tridentate N′-(2-hy­droxy­benzyl­idene)benzo­hydrazide (H2sabhz) ligand can lead to variations in the resulting supra­molecular structure. The title compound, [Pb2(C14H10N2O2)2], was prepared by the reaction of [Pb(OAc)2]·3H2O (OAc is acetate) with the benzoyl­hydrazone derivative of salicyl­aldehyde, i.e. H2sabhz, in the presence of tri­ethyl­amine in methanol. In the crystal structure, each PbII atom of the dimer has an NO3 coordination environment, with one sabhz ligand coordinating in an O,N,O′-manner and with the second sabhz ligand coordinating via the bridging phenolate O atom, since the dimers are located on a centre of inversion. It has been found that the dimers are connected by Pb...N inter­actions, resulting in a two-dimensional supra­molecular network which shows the [32.52,3.53] net topology. The s2 electron pair of the PbII ion clearly influences the observed inter­molecular inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616008755/lg3189sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616008755/lg3189Isup2.hkl
Contains datablock I

CCDC reference: 1482579

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Bis[µ2-N'-(2-oxidobenzylidene)benzohydrazidato-κ4O:O,N',O']dilead(II) top
Crystal data top
[Pb2(C14H10N2O2)2]Z = 2
Mr = 890.86F(000) = 824
Triclinic, P1Dx = 2.297 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3754 (7) ÅCell parameters from 9872 reflections
b = 12.6354 (10) Åθ = 2.8–28.3°
c = 13.6686 (11) ŵ = 13.10 mm1
α = 112.213 (3)°T = 300 K
β = 101.395 (3)°Plate
γ = 95.781 (3)°0.11 × 0.06 × 0.05 mm
V = 1287.99 (18) Å3
Data collection top
Bruker APEXII CCD
diffractometer
Rint = 0.036
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
θmax = 28.4°, θmin = 2.5°
Tmin = 0.526, Tmax = 0.746h = 1111
45814 measured reflectionsk = 1616
6413 independent reflectionsl = 1818
5551 reflections with I > 2σ(I)
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.018H-atom parameters constrained
wR(F2) = 0.037 w = 1/[σ2(Fo2) + (0.0126P)2 + 0.6635P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.002
6413 reflectionsΔρmax = 0.35 e Å3
343 parametersΔρmin = 0.83 e Å3
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pb1A0.30861 (2)0.58062 (2)0.50254 (2)0.03340 (3)
O1A0.5022 (2)0.50480 (18)0.60080 (15)0.0384 (5)
O2A0.1000 (2)0.47024 (18)0.34376 (16)0.0406 (5)
N1A0.1560 (3)0.41253 (18)0.51006 (17)0.0296 (5)
N2A0.0066 (3)0.35826 (19)0.42986 (18)0.0323 (5)
C1A0.4796 (3)0.4751 (2)0.6818 (2)0.0314 (6)
C2A0.6111 (3)0.5049 (3)0.7748 (2)0.0392 (6)
H2A0.71230.54760.78050.047*
C3A0.5922 (4)0.4717 (3)0.8576 (2)0.0413 (7)
H3A0.68090.4930.91870.05*
C4A0.4447 (4)0.4077 (3)0.8520 (2)0.0432 (7)
H4A0.4340.38450.90770.052*
C5A0.3139 (4)0.3787 (2)0.7625 (2)0.0379 (6)
H5A0.21410.33570.75830.046*
C6A0.3264 (3)0.4123 (2)0.6768 (2)0.0293 (5)
C7A0.1797 (3)0.3771 (2)0.5874 (2)0.0304 (5)
H7A0.09350.32340.58570.037*
C8A0.0028 (3)0.3905 (2)0.3481 (2)0.0332 (6)
C9A0.1453 (3)0.3260 (3)0.2512 (2)0.0377 (6)
C10A0.2442 (4)0.2256 (3)0.2388 (3)0.0591 (9)
H10A0.22310.19670.29230.071*
C11A0.3751 (5)0.1674 (4)0.1466 (3)0.0792 (14)
H11A0.4420.09980.13860.095*
C12A0.4059 (5)0.2095 (4)0.0675 (3)0.0773 (14)
H12A0.49450.17060.0060.093*
C13A0.3079 (5)0.3078 (4)0.0780 (3)0.0688 (12)
H13A0.32920.33510.02330.083*
C14A0.1769 (4)0.3674 (3)0.1692 (2)0.0494 (8)
H14A0.11030.43460.17610.059*
Pb1B0.77237 (2)0.08040 (2)0.47237 (2)0.03558 (3)
O1B1.0121 (2)0.04723 (18)0.60986 (16)0.0397 (5)
O2B0.5972 (3)0.04032 (18)0.34333 (16)0.0446 (5)
N1B0.7023 (3)0.11001 (19)0.54610 (18)0.0324 (5)
N2B0.5687 (3)0.12917 (19)0.47991 (18)0.0348 (5)
C1B1.0122 (3)0.1219 (2)0.7105 (2)0.0335 (6)
C2B1.1355 (4)0.1321 (3)0.8009 (3)0.0443 (7)
H2B1.21360.08420.79120.053*
C3B1.1424 (4)0.2125 (3)0.9044 (3)0.0510 (8)
H3B1.22470.21730.96360.061*
C4B1.0303 (4)0.2852 (3)0.9216 (3)0.0557 (9)
H4B1.03730.33990.99150.067*
C5B0.9073 (4)0.2761 (3)0.8341 (3)0.0479 (8)
H5B0.83160.32570.84560.057*
C6B0.8931 (3)0.1938 (2)0.7277 (2)0.0340 (6)
C7B0.7554 (3)0.1906 (2)0.6429 (2)0.0357 (6)
H7B0.70040.2530.66040.043*
C8B0.5305 (3)0.0489 (2)0.3789 (2)0.0324 (6)
C9B0.3971 (3)0.0648 (2)0.2984 (2)0.0322 (6)
C10B0.3363 (4)0.1673 (3)0.3229 (2)0.0408 (7)
H10B0.37320.22650.39280.049*
C11B0.2207 (4)0.1814 (3)0.2435 (3)0.0563 (9)
H11B0.18250.25110.25930.068*
C12B0.1623 (4)0.0921 (3)0.1410 (3)0.0601 (9)
H12B0.08470.10180.08770.072*
C13B0.2180 (4)0.0109 (3)0.1170 (3)0.0529 (8)
H13B0.17590.07130.04810.063*
C14B0.3359 (4)0.0256 (3)0.1942 (2)0.0423 (7)
H14B0.37460.09510.17710.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb1A0.02539 (5)0.03970 (6)0.03983 (6)0.00318 (4)0.01028 (4)0.02113 (5)
O1A0.0265 (9)0.0655 (13)0.0364 (10)0.0106 (9)0.0132 (8)0.0319 (10)
O2A0.0304 (10)0.0584 (13)0.0388 (11)0.0033 (9)0.0096 (8)0.0271 (10)
N1A0.0251 (11)0.0335 (11)0.0296 (11)0.0048 (9)0.0078 (9)0.0121 (9)
N2A0.0253 (11)0.0361 (12)0.0315 (12)0.0016 (9)0.0056 (9)0.0115 (10)
C1A0.0292 (13)0.0425 (15)0.0296 (13)0.0141 (11)0.0131 (11)0.0179 (12)
C2A0.0276 (14)0.0575 (18)0.0359 (15)0.0070 (13)0.0109 (11)0.0215 (14)
C3A0.0379 (16)0.0576 (19)0.0317 (15)0.0123 (14)0.0072 (12)0.0219 (14)
C4A0.0500 (18)0.0553 (18)0.0340 (15)0.0111 (15)0.0124 (13)0.0274 (14)
C5A0.0390 (16)0.0430 (16)0.0386 (15)0.0045 (12)0.0128 (12)0.0234 (13)
C6A0.0307 (13)0.0310 (13)0.0300 (13)0.0086 (10)0.0113 (10)0.0142 (11)
C7A0.0292 (13)0.0288 (13)0.0356 (14)0.0055 (10)0.0100 (11)0.0146 (11)
C8A0.0229 (13)0.0439 (15)0.0308 (14)0.0084 (11)0.0086 (10)0.0118 (12)
C9A0.0267 (14)0.0519 (17)0.0307 (14)0.0114 (12)0.0094 (11)0.0106 (13)
C10A0.0476 (19)0.076 (2)0.0379 (18)0.0128 (17)0.0081 (15)0.0135 (17)
C11A0.052 (2)0.106 (3)0.045 (2)0.028 (2)0.0095 (17)0.005 (2)
C12A0.038 (2)0.125 (4)0.035 (2)0.015 (2)0.0004 (15)0.001 (2)
C13A0.061 (2)0.099 (3)0.0372 (19)0.035 (2)0.0021 (17)0.018 (2)
C14A0.0506 (19)0.062 (2)0.0350 (16)0.0240 (16)0.0096 (14)0.0162 (15)
Pb1B0.02857 (6)0.03555 (6)0.04498 (7)0.01248 (4)0.01379 (5)0.01524 (5)
O1B0.0261 (10)0.0526 (12)0.0382 (11)0.0107 (9)0.0113 (8)0.0139 (9)
O2B0.0389 (11)0.0518 (12)0.0380 (11)0.0230 (10)0.0092 (9)0.0098 (9)
N1B0.0248 (11)0.0353 (12)0.0364 (12)0.0074 (9)0.0066 (9)0.0140 (10)
N2B0.0292 (12)0.0375 (12)0.0355 (12)0.0093 (9)0.0041 (9)0.0137 (10)
C1B0.0254 (13)0.0419 (15)0.0351 (14)0.0026 (11)0.0113 (11)0.0167 (12)
C2B0.0321 (15)0.064 (2)0.0461 (18)0.0131 (14)0.0114 (13)0.0304 (16)
C3B0.0363 (17)0.076 (2)0.0360 (17)0.0044 (16)0.0014 (13)0.0237 (16)
C4B0.0420 (18)0.073 (2)0.0347 (17)0.0035 (16)0.0060 (14)0.0068 (16)
C5B0.0386 (17)0.0500 (18)0.0430 (17)0.0103 (14)0.0094 (14)0.0061 (14)
C6B0.0292 (13)0.0365 (14)0.0329 (14)0.0025 (11)0.0084 (11)0.0112 (12)
C7B0.0308 (14)0.0343 (14)0.0402 (16)0.0089 (11)0.0094 (12)0.0127 (12)
C8B0.0253 (13)0.0356 (14)0.0377 (15)0.0070 (11)0.0124 (11)0.0141 (12)
C9B0.0216 (12)0.0404 (15)0.0366 (14)0.0049 (11)0.0093 (11)0.0170 (12)
C10B0.0321 (15)0.0442 (16)0.0418 (16)0.0098 (12)0.0080 (12)0.0132 (13)
C11B0.0456 (19)0.062 (2)0.065 (2)0.0261 (17)0.0087 (16)0.0286 (19)
C12B0.0405 (19)0.084 (3)0.052 (2)0.0200 (18)0.0027 (15)0.0284 (19)
C13B0.0408 (18)0.063 (2)0.0410 (18)0.0066 (16)0.0011 (14)0.0124 (16)
C14B0.0371 (16)0.0456 (17)0.0417 (17)0.0078 (13)0.0096 (13)0.0156 (14)
Geometric parameters (Å, º) top
Pb1A—O2A2.330 (2)Pb1B—O2B2.307 (2)
Pb1A—O1Ai2.3974 (19)Pb1B—O1Biii2.3881 (19)
Pb1A—O1A2.4032 (18)Pb1B—O1B2.3935 (19)
Pb1A—N1A2.413 (2)Pb1B—N1B2.415 (2)
Pb1A—N2Aii3.042 (3)Pb1B—N2Biv3.107 (3)
O1A—C1A1.336 (3)O1B—C1B1.342 (3)
O1A—Pb1Ai2.3973 (19)O1B—Pb1Biii2.3881 (19)
O2A—C8A1.284 (3)O2B—C8B1.281 (3)
N1A—C7A1.285 (3)N1B—C7B1.282 (3)
N1A—N2A1.398 (3)N1B—N2B1.396 (3)
N2A—C8A1.319 (3)N2B—C8B1.318 (3)
C1A—C2A1.404 (4)C1B—C2B1.400 (4)
C1A—C6A1.414 (4)C1B—C6B1.411 (4)
C2A—C3A1.379 (4)C2B—C3B1.380 (4)
C2A—H2A0.93C2B—H2B0.93
C3A—C4A1.379 (4)C3B—C4B1.371 (5)
C3A—H3A0.93C3B—H3B0.93
C4A—C5A1.372 (4)C4B—C5B1.375 (4)
C4A—H4A0.93C4B—H4B0.93
C5A—C6A1.406 (4)C5B—C6B1.405 (4)
C5A—H5A0.93C5B—H5B0.93
C6A—C7A1.444 (4)C6B—C7B1.450 (4)
C7A—H7A0.93C7B—H7B0.93
C8A—C9A1.486 (4)C8B—C9B1.492 (4)
C9A—C10A1.376 (5)C9B—C10B1.386 (4)
C9A—C14A1.397 (4)C9B—C14B1.400 (4)
C10A—C11A1.386 (5)C10B—C11B1.383 (4)
C10A—H10A0.93C10B—H10B0.93
C11A—C12A1.368 (6)C11B—C12B1.378 (5)
C11A—H11A0.93C11B—H11B0.93
C12A—C13A1.360 (6)C12B—C13B1.371 (5)
C12A—H12A0.93C12B—H12B0.93
C13A—C14A1.381 (5)C13B—C14B1.377 (4)
C13A—H13A0.93C13B—H13B0.93
C14A—H14A0.93C14B—H14B0.93
O2A—Pb1A—O1Ai85.92 (7)O2B—Pb1B—O1Biii86.73 (7)
O2A—Pb1A—O1A125.74 (7)O2B—Pb1B—O1B127.32 (7)
O1Ai—Pb1A—O1A68.58 (7)O1Biii—Pb1B—O1B69.80 (8)
O2A—Pb1A—N1A66.78 (7)O2B—Pb1B—N1B66.89 (7)
O1Ai—Pb1A—N1A101.56 (7)O1Biii—Pb1B—N1B102.25 (7)
O1A—Pb1A—N1A72.48 (7)O1B—Pb1B—N1B72.92 (7)
C1A—O1A—Pb1Ai119.29 (16)C1B—O1B—Pb1Biii120.53 (16)
C1A—O1A—Pb1A125.62 (16)C1B—O1B—Pb1B125.45 (16)
Pb1Ai—O1A—Pb1A111.42 (7)Pb1Biii—O1B—Pb1B110.20 (8)
C8A—O2A—Pb1A116.58 (16)C8B—O2B—Pb1B116.82 (17)
C7A—N1A—N2A114.7 (2)C7B—N1B—N2B114.6 (2)
C7A—N1A—Pb1A128.26 (17)C7B—N1B—Pb1B129.00 (18)
N2A—N1A—Pb1A116.06 (15)N2B—N1B—Pb1B115.69 (15)
C8A—N2A—N1A111.5 (2)C8B—N2B—N1B111.4 (2)
O1A—C1A—C2A119.9 (2)O1B—C1B—C2B119.9 (3)
O1A—C1A—C6A122.0 (2)O1B—C1B—C6B121.5 (2)
C2A—C1A—C6A118.1 (2)C2B—C1B—C6B118.6 (3)
C3A—C2A—C1A120.9 (3)C3B—C2B—C1B120.7 (3)
C3A—C2A—H2A119.6C3B—C2B—H2B119.6
C1A—C2A—H2A119.6C1B—C2B—H2B119.6
C2A—C3A—C4A121.4 (3)C4B—C3B—C2B121.2 (3)
C2A—C3A—H3A119.3C4B—C3B—H3B119.4
C4A—C3A—H3A119.3C2B—C3B—H3B119.4
C5A—C4A—C3A118.7 (3)C3B—C4B—C5B119.1 (3)
C5A—C4A—H4A120.6C3B—C4B—H4B120.5
C3A—C4A—H4A120.6C5B—C4B—H4B120.5
C4A—C5A—C6A121.9 (3)C4B—C5B—C6B121.7 (3)
C4A—C5A—H5A119C4B—C5B—H5B119.1
C6A—C5A—H5A119C6B—C5B—H5B119.1
C5A—C6A—C1A119.0 (2)C5B—C6B—C1B118.7 (3)
C5A—C6A—C7A116.7 (2)C5B—C6B—C7B116.5 (3)
C1A—C6A—C7A124.3 (2)C1B—C6B—C7B124.9 (2)
N1A—C7A—C6A126.7 (2)N1B—C7B—C6B126.2 (3)
N1A—C7A—H7A116.7N1B—C7B—H7B116.9
C6A—C7A—H7A116.7C6B—C7B—H7B116.9
O2A—C8A—N2A126.4 (2)O2B—C8B—N2B126.5 (2)
O2A—C8A—C9A117.6 (2)O2B—C8B—C9B117.1 (2)
N2A—C8A—C9A116.0 (2)N2B—C8B—C9B116.4 (2)
C10A—C9A—C14A119.3 (3)C10B—C9B—C14B119.4 (3)
C10A—C9A—C8A122.0 (3)C10B—C9B—C8B121.9 (2)
C14A—C9A—C8A118.7 (3)C14B—C9B—C8B118.6 (2)
C9A—C10A—C11A120.2 (4)C11B—C10B—C9B120.0 (3)
C9A—C10A—H10A119.9C11B—C10B—H10B120
C11A—C10A—H10A119.9C9B—C10B—H10B120
C12A—C11A—C10A120.0 (4)C12B—C11B—C10B120.0 (3)
C12A—C11A—H11A120C12B—C11B—H11B120
C10A—C11A—H11A120C10B—C11B—H11B120
C13A—C12A—C11A120.4 (3)C13B—C12B—C11B120.4 (3)
C13A—C12A—H12A119.8C13B—C12B—H12B119.8
C11A—C12A—H12A119.8C11B—C12B—H12B119.8
C12A—C13A—C14A120.6 (4)C12B—C13B—C14B120.5 (3)
C12A—C13A—H13A119.7C12B—C13B—H13B119.8
C14A—C13A—H13A119.7C14B—C13B—H13B119.8
C13A—C14A—C9A119.5 (4)C13B—C14B—C9B119.6 (3)
C13A—C14A—H14A120.3C13B—C14B—H14B120.2
C9A—C14A—H14A120.3C9B—C14B—H14B120.2
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x+2, y, z+1; (iv) x+1, y, z+1.
 

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