Inter­molecular Pb...N inter­actions in lead(II) dimers producing a supra­molecular two-dimensional metal–organic compound: bis­[μ₂-N′-(2-oxido­benzyl­idene)benzohydrazidato-κ⁴O:O,N′,O′]dilead(II)

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 Pb^II 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 Pb^II ion clearly influences the observed inter­molecular inter­actions.

Computing details

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)

Crystal data

[Pb2(C14H10N2O2)2]	Z = 2
Mr = 890.86	F(000) = 824
Triclinic, P1	Dx = 2.297 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3754 (7) Å	Cell parameters from 9872 reflections
b = 12.6354 (10) Å	θ = 2.8–28.3°
c = 13.6686 (11) Å	µ = 13.10 mm^−1
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) Å^3

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.036
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θmax = 28.4°, θmin = 2.5°
Tmin = 0.526, Tmax = 0.746	h = −11→11
45814 measured reflections	k = −16→16
6413 independent reflections	l = −18→18
5551 reflections with I > 2σ(I)

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.018	H-atom parameters constrained
wR(F^2) = 0.037	w = 1/[σ^2(Fo^2) + (0.0126P)^2 + 0.6635P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
6413 reflections	Δρmax = 0.35 e Å^−3
343 parameters	Δρmin = −0.83 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Pb1A	0.30861 (2)	0.58062 (2)	0.50254 (2)	0.03340 (3)
O1A	0.5022 (2)	0.50480 (18)	0.60080 (15)	0.0384 (5)
O2A	0.1000 (2)	0.47024 (18)	0.34376 (16)	0.0406 (5)
N1A	0.1560 (3)	0.41253 (18)	0.51006 (17)	0.0296 (5)
N2A	0.0066 (3)	0.35826 (19)	0.42986 (18)	0.0323 (5)
C1A	0.4796 (3)	0.4751 (2)	0.6818 (2)	0.0314 (6)
C2A	0.6111 (3)	0.5049 (3)	0.7748 (2)	0.0392 (6)
H2A	0.7123	0.5476	0.7805	0.047*
C3A	0.5922 (4)	0.4717 (3)	0.8576 (2)	0.0413 (7)
H3A	0.6809	0.493	0.9187	0.05*
C4A	0.4447 (4)	0.4077 (3)	0.8520 (2)	0.0432 (7)
H4A	0.434	0.3845	0.9077	0.052*
C5A	0.3139 (4)	0.3787 (2)	0.7625 (2)	0.0379 (6)
H5A	0.2141	0.3357	0.7583	0.046*
C6A	0.3264 (3)	0.4123 (2)	0.6768 (2)	0.0293 (5)
C7A	0.1797 (3)	0.3771 (2)	0.5874 (2)	0.0304 (5)
H7A	0.0935	0.3234	0.5857	0.037*
C8A	−0.0028 (3)	0.3905 (2)	0.3481 (2)	0.0332 (6)
C9A	−0.1453 (3)	0.3260 (3)	0.2512 (2)	0.0377 (6)
C10A	−0.2442 (4)	0.2256 (3)	0.2388 (3)	0.0591 (9)
H10A	−0.2231	0.1967	0.2923	0.071*
C11A	−0.3751 (5)	0.1674 (4)	0.1466 (3)	0.0792 (14)
H11A	−0.442	0.0998	0.1386	0.095*
C12A	−0.4059 (5)	0.2095 (4)	0.0675 (3)	0.0773 (14)
H12A	−0.4945	0.1706	0.006	0.093*
C13A	−0.3079 (5)	0.3078 (4)	0.0780 (3)	0.0688 (12)
H13A	−0.3292	0.3351	0.0233	0.083*
C14A	−0.1769 (4)	0.3674 (3)	0.1692 (2)	0.0494 (8)
H14A	−0.1103	0.4346	0.1761	0.059*
Pb1B	0.77237 (2)	−0.08040 (2)	0.47237 (2)	0.03558 (3)
O1B	1.0121 (2)	0.04723 (18)	0.60986 (16)	0.0397 (5)
O2B	0.5972 (3)	−0.04032 (18)	0.34333 (16)	0.0446 (5)
N1B	0.7023 (3)	0.11001 (19)	0.54610 (18)	0.0324 (5)
N2B	0.5687 (3)	0.12917 (19)	0.47991 (18)	0.0348 (5)
C1B	1.0122 (3)	0.1219 (2)	0.7105 (2)	0.0335 (6)
C2B	1.1355 (4)	0.1321 (3)	0.8009 (3)	0.0443 (7)
H2B	1.2136	0.0842	0.7912	0.053*
C3B	1.1424 (4)	0.2125 (3)	0.9044 (3)	0.0510 (8)
H3B	1.2247	0.2173	0.9636	0.061*
C4B	1.0303 (4)	0.2852 (3)	0.9216 (3)	0.0557 (9)
H4B	1.0373	0.3399	0.9915	0.067*
C5B	0.9073 (4)	0.2761 (3)	0.8341 (3)	0.0479 (8)
H5B	0.8316	0.3257	0.8456	0.057*
C6B	0.8931 (3)	0.1938 (2)	0.7277 (2)	0.0340 (6)
C7B	0.7554 (3)	0.1906 (2)	0.6429 (2)	0.0357 (6)
H7B	0.7004	0.253	0.6604	0.043*
C8B	0.5305 (3)	0.0489 (2)	0.3789 (2)	0.0324 (6)
C9B	0.3971 (3)	0.0648 (2)	0.2984 (2)	0.0322 (6)
C10B	0.3363 (4)	0.1673 (3)	0.3229 (2)	0.0408 (7)
H10B	0.3732	0.2265	0.3928	0.049*
C11B	0.2207 (4)	0.1814 (3)	0.2435 (3)	0.0563 (9)
H11B	0.1825	0.2511	0.2593	0.068*
C12B	0.1623 (4)	0.0921 (3)	0.1410 (3)	0.0601 (9)
H12B	0.0847	0.1018	0.0877	0.072*
C13B	0.2180 (4)	−0.0109 (3)	0.1170 (3)	0.0529 (8)
H13B	0.1759	−0.0713	0.0481	0.063*
C14B	0.3359 (4)	−0.0256 (3)	0.1942 (2)	0.0423 (7)
H14B	0.3746	−0.0951	0.1771	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pb1A	0.02539 (5)	0.03970 (6)	0.03983 (6)	0.00318 (4)	0.01028 (4)	0.02113 (5)
O1A	0.0265 (9)	0.0655 (13)	0.0364 (10)	0.0106 (9)	0.0132 (8)	0.0319 (10)
O2A	0.0304 (10)	0.0584 (13)	0.0388 (11)	0.0033 (9)	0.0096 (8)	0.0271 (10)
N1A	0.0251 (11)	0.0335 (11)	0.0296 (11)	0.0048 (9)	0.0078 (9)	0.0121 (9)
N2A	0.0253 (11)	0.0361 (12)	0.0315 (12)	0.0016 (9)	0.0056 (9)	0.0115 (10)
C1A	0.0292 (13)	0.0425 (15)	0.0296 (13)	0.0141 (11)	0.0131 (11)	0.0179 (12)
C2A	0.0276 (14)	0.0575 (18)	0.0359 (15)	0.0070 (13)	0.0109 (11)	0.0215 (14)
C3A	0.0379 (16)	0.0576 (19)	0.0317 (15)	0.0123 (14)	0.0072 (12)	0.0219 (14)
C4A	0.0500 (18)	0.0553 (18)	0.0340 (15)	0.0111 (15)	0.0124 (13)	0.0274 (14)
C5A	0.0390 (16)	0.0430 (16)	0.0386 (15)	0.0045 (12)	0.0128 (12)	0.0234 (13)
C6A	0.0307 (13)	0.0310 (13)	0.0300 (13)	0.0086 (10)	0.0113 (10)	0.0142 (11)
C7A	0.0292 (13)	0.0288 (13)	0.0356 (14)	0.0055 (10)	0.0100 (11)	0.0146 (11)
C8A	0.0229 (13)	0.0439 (15)	0.0308 (14)	0.0084 (11)	0.0086 (10)	0.0118 (12)
C9A	0.0267 (14)	0.0519 (17)	0.0307 (14)	0.0114 (12)	0.0094 (11)	0.0106 (13)
C10A	0.0476 (19)	0.076 (2)	0.0379 (18)	−0.0128 (17)	0.0081 (15)	0.0135 (17)
C11A	0.052 (2)	0.106 (3)	0.045 (2)	−0.028 (2)	0.0095 (17)	0.005 (2)
C12A	0.038 (2)	0.125 (4)	0.035 (2)	0.015 (2)	0.0004 (15)	0.001 (2)
C13A	0.061 (2)	0.099 (3)	0.0372 (19)	0.035 (2)	0.0021 (17)	0.018 (2)
C14A	0.0506 (19)	0.062 (2)	0.0350 (16)	0.0240 (16)	0.0096 (14)	0.0162 (15)
Pb1B	0.02857 (6)	0.03555 (6)	0.04498 (7)	0.01248 (4)	0.01379 (5)	0.01524 (5)
O1B	0.0261 (10)	0.0526 (12)	0.0382 (11)	0.0107 (9)	0.0113 (8)	0.0139 (9)
O2B	0.0389 (11)	0.0518 (12)	0.0380 (11)	0.0230 (10)	0.0092 (9)	0.0098 (9)
N1B	0.0248 (11)	0.0353 (12)	0.0364 (12)	0.0074 (9)	0.0066 (9)	0.0140 (10)
N2B	0.0292 (12)	0.0375 (12)	0.0355 (12)	0.0093 (9)	0.0041 (9)	0.0137 (10)
C1B	0.0254 (13)	0.0419 (15)	0.0351 (14)	0.0026 (11)	0.0113 (11)	0.0167 (12)
C2B	0.0321 (15)	0.064 (2)	0.0461 (18)	0.0131 (14)	0.0114 (13)	0.0304 (16)
C3B	0.0363 (17)	0.076 (2)	0.0360 (17)	0.0044 (16)	0.0014 (13)	0.0237 (16)
C4B	0.0420 (18)	0.073 (2)	0.0347 (17)	0.0035 (16)	0.0060 (14)	0.0068 (16)
C5B	0.0386 (17)	0.0500 (18)	0.0430 (17)	0.0103 (14)	0.0094 (14)	0.0061 (14)
C6B	0.0292 (13)	0.0365 (14)	0.0329 (14)	0.0025 (11)	0.0084 (11)	0.0112 (12)
C7B	0.0308 (14)	0.0343 (14)	0.0402 (16)	0.0089 (11)	0.0094 (12)	0.0127 (12)
C8B	0.0253 (13)	0.0356 (14)	0.0377 (15)	0.0070 (11)	0.0124 (11)	0.0141 (12)
C9B	0.0216 (12)	0.0404 (15)	0.0366 (14)	0.0049 (11)	0.0093 (11)	0.0170 (12)
C10B	0.0321 (15)	0.0442 (16)	0.0418 (16)	0.0098 (12)	0.0080 (12)	0.0132 (13)
C11B	0.0456 (19)	0.062 (2)	0.065 (2)	0.0261 (17)	0.0087 (16)	0.0286 (19)
C12B	0.0405 (19)	0.084 (3)	0.052 (2)	0.0200 (18)	−0.0027 (15)	0.0284 (19)
C13B	0.0408 (18)	0.063 (2)	0.0410 (18)	0.0066 (16)	0.0011 (14)	0.0124 (16)
C14B	0.0371 (16)	0.0456 (17)	0.0417 (17)	0.0078 (13)	0.0096 (13)	0.0156 (14)

Geometric parameters (Å, º)

Pb1A—O2A	2.330 (2)	Pb1B—O2B	2.307 (2)
Pb1A—O1A^i	2.3974 (19)	Pb1B—O1B^iii	2.3881 (19)
Pb1A—O1A	2.4032 (18)	Pb1B—O1B	2.3935 (19)
Pb1A—N1A	2.413 (2)	Pb1B—N1B	2.415 (2)
Pb1A—N2A^ii	3.042 (3)	Pb1B—N2B^iv	3.107 (3)
O1A—C1A	1.336 (3)	O1B—C1B	1.342 (3)
O1A—Pb1A^i	2.3973 (19)	O1B—Pb1B^iii	2.3881 (19)
O2A—C8A	1.284 (3)	O2B—C8B	1.281 (3)
N1A—C7A	1.285 (3)	N1B—C7B	1.282 (3)
N1A—N2A	1.398 (3)	N1B—N2B	1.396 (3)
N2A—C8A	1.319 (3)	N2B—C8B	1.318 (3)
C1A—C2A	1.404 (4)	C1B—C2B	1.400 (4)
C1A—C6A	1.414 (4)	C1B—C6B	1.411 (4)
C2A—C3A	1.379 (4)	C2B—C3B	1.380 (4)
C2A—H2A	0.93	C2B—H2B	0.93
C3A—C4A	1.379 (4)	C3B—C4B	1.371 (5)
C3A—H3A	0.93	C3B—H3B	0.93
C4A—C5A	1.372 (4)	C4B—C5B	1.375 (4)
C4A—H4A	0.93	C4B—H4B	0.93
C5A—C6A	1.406 (4)	C5B—C6B	1.405 (4)
C5A—H5A	0.93	C5B—H5B	0.93
C6A—C7A	1.444 (4)	C6B—C7B	1.450 (4)
C7A—H7A	0.93	C7B—H7B	0.93
C8A—C9A	1.486 (4)	C8B—C9B	1.492 (4)
C9A—C10A	1.376 (5)	C9B—C10B	1.386 (4)
C9A—C14A	1.397 (4)	C9B—C14B	1.400 (4)
C10A—C11A	1.386 (5)	C10B—C11B	1.383 (4)
C10A—H10A	0.93	C10B—H10B	0.93
C11A—C12A	1.368 (6)	C11B—C12B	1.378 (5)
C11A—H11A	0.93	C11B—H11B	0.93
C12A—C13A	1.360 (6)	C12B—C13B	1.371 (5)
C12A—H12A	0.93	C12B—H12B	0.93
C13A—C14A	1.381 (5)	C13B—C14B	1.377 (4)
C13A—H13A	0.93	C13B—H13B	0.93
C14A—H14A	0.93	C14B—H14B	0.93
O2A—Pb1A—O1A^i	85.92 (7)	O2B—Pb1B—O1B^iii	86.73 (7)
O2A—Pb1A—O1A	125.74 (7)	O2B—Pb1B—O1B	127.32 (7)
O1A^i—Pb1A—O1A	68.58 (7)	O1B^iii—Pb1B—O1B	69.80 (8)
O2A—Pb1A—N1A	66.78 (7)	O2B—Pb1B—N1B	66.89 (7)
O1A^i—Pb1A—N1A	101.56 (7)	O1B^iii—Pb1B—N1B	102.25 (7)
O1A—Pb1A—N1A	72.48 (7)	O1B—Pb1B—N1B	72.92 (7)
C1A—O1A—Pb1A^i	119.29 (16)	C1B—O1B—Pb1B^iii	120.53 (16)
C1A—O1A—Pb1A	125.62 (16)	C1B—O1B—Pb1B	125.45 (16)
Pb1A^i—O1A—Pb1A	111.42 (7)	Pb1B^iii—O1B—Pb1B	110.20 (8)
C8A—O2A—Pb1A	116.58 (16)	C8B—O2B—Pb1B	116.82 (17)
C7A—N1A—N2A	114.7 (2)	C7B—N1B—N2B	114.6 (2)
C7A—N1A—Pb1A	128.26 (17)	C7B—N1B—Pb1B	129.00 (18)
N2A—N1A—Pb1A	116.06 (15)	N2B—N1B—Pb1B	115.69 (15)
C8A—N2A—N1A	111.5 (2)	C8B—N2B—N1B	111.4 (2)
O1A—C1A—C2A	119.9 (2)	O1B—C1B—C2B	119.9 (3)
O1A—C1A—C6A	122.0 (2)	O1B—C1B—C6B	121.5 (2)
C2A—C1A—C6A	118.1 (2)	C2B—C1B—C6B	118.6 (3)
C3A—C2A—C1A	120.9 (3)	C3B—C2B—C1B	120.7 (3)
C3A—C2A—H2A	119.6	C3B—C2B—H2B	119.6
C1A—C2A—H2A	119.6	C1B—C2B—H2B	119.6
C2A—C3A—C4A	121.4 (3)	C4B—C3B—C2B	121.2 (3)
C2A—C3A—H3A	119.3	C4B—C3B—H3B	119.4
C4A—C3A—H3A	119.3	C2B—C3B—H3B	119.4
C5A—C4A—C3A	118.7 (3)	C3B—C4B—C5B	119.1 (3)
C5A—C4A—H4A	120.6	C3B—C4B—H4B	120.5
C3A—C4A—H4A	120.6	C5B—C4B—H4B	120.5
C4A—C5A—C6A	121.9 (3)	C4B—C5B—C6B	121.7 (3)
C4A—C5A—H5A	119	C4B—C5B—H5B	119.1
C6A—C5A—H5A	119	C6B—C5B—H5B	119.1
C5A—C6A—C1A	119.0 (2)	C5B—C6B—C1B	118.7 (3)
C5A—C6A—C7A	116.7 (2)	C5B—C6B—C7B	116.5 (3)
C1A—C6A—C7A	124.3 (2)	C1B—C6B—C7B	124.9 (2)
N1A—C7A—C6A	126.7 (2)	N1B—C7B—C6B	126.2 (3)
N1A—C7A—H7A	116.7	N1B—C7B—H7B	116.9
C6A—C7A—H7A	116.7	C6B—C7B—H7B	116.9
O2A—C8A—N2A	126.4 (2)	O2B—C8B—N2B	126.5 (2)
O2A—C8A—C9A	117.6 (2)	O2B—C8B—C9B	117.1 (2)
N2A—C8A—C9A	116.0 (2)	N2B—C8B—C9B	116.4 (2)
C10A—C9A—C14A	119.3 (3)	C10B—C9B—C14B	119.4 (3)
C10A—C9A—C8A	122.0 (3)	C10B—C9B—C8B	121.9 (2)
C14A—C9A—C8A	118.7 (3)	C14B—C9B—C8B	118.6 (2)
C9A—C10A—C11A	120.2 (4)	C11B—C10B—C9B	120.0 (3)
C9A—C10A—H10A	119.9	C11B—C10B—H10B	120
C11A—C10A—H10A	119.9	C9B—C10B—H10B	120
C12A—C11A—C10A	120.0 (4)	C12B—C11B—C10B	120.0 (3)
C12A—C11A—H11A	120	C12B—C11B—H11B	120
C10A—C11A—H11A	120	C10B—C11B—H11B	120
C13A—C12A—C11A	120.4 (3)	C13B—C12B—C11B	120.4 (3)
C13A—C12A—H12A	119.8	C13B—C12B—H12B	119.8
C11A—C12A—H12A	119.8	C11B—C12B—H12B	119.8
C12A—C13A—C14A	120.6 (4)	C12B—C13B—C14B	120.5 (3)
C12A—C13A—H13A	119.7	C12B—C13B—H13B	119.8
C14A—C13A—H13A	119.7	C14B—C13B—H13B	119.8
C13A—C14A—C9A	119.5 (4)	C13B—C14B—C9B	119.6 (3)
C13A—C14A—H14A	120.3	C13B—C14B—H14B	120.2
C9A—C14A—H14A	120.3	C9B—C14B—H14B	120.2

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.