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Acta Cryst. (2007). E63, m1792    [ doi:10.1107/S1600536807025615 ]

[Bis(1H-benzimidazol-2-ylmethyl)amine-[kappa]3N,N',N'']dinitratolead(II)

Y. Zhang, X.-Y. Xia, X.-Q. Liu, X.-M. Chen and T. Liu

Abstract top

In the title compound, [Pb(NO3)2(C16H15N5)], the PbII ion is chelated by three N atoms of a bis(1H-benzimidazol-2-ylmethyl)amine (IDB) ligand and two O atoms from each of two nitrate ligands, resulting in an asymmetric seven-coordinate configuration. The crystal structure is stabilized by intermolecular N-H...O and C-H...O hydrogen bonds and [pi]-[pi] interactions, with ring-centroid separations of 3.578 (5) and 3.686 (5) Å, leading to a three-dimensional network.

Comment top

The lead(II) complexes with N-donor ligands have been widely studied in recent years (Ali & Ali, 2002; Ali et al., 2005). As part of our continuing studies on the ligands or metal complexes containing multi-benzimidazole groups (Zhang et al. 2005), We report herein the crystal structure of the title compound, [Bis(1H-benzimidazol-2-ylmethyl)amine]dinitrolead(II), (I).

In (I) (Fig.1), the Pb atom is seven-coordinated by three nitrogen atoms of IDB and four oxygen atoms of two nitrides, resulting a rather asymmetric configuration. The seven donor atoms occupy half of the space environment around the lead ion, leaving a zone free from co-ordinated donor atoms, which is occupied by the lone pair of Pb around the lead ion (Byriel et al.,1992).

In the crystal structure, the molecules are linked into a three-dimensional framework by intermolecular N—H–O and C—H–O hydrogen bonds (Table 1 and Fig. 2). π-π stacking interactions are also observed between the adjacent imidazole rings. The imidazole ring of N2/N3/C2/C3/C8 at (x,y,z) and (1 − x,1 − y,1 − z) have a ring centroid separation of 3.578 (5) Å and an interplanar spacing of ca 3.521 Å. Similarly, the N4/N5/C10/C11/C16 rings at (x,y,z) and (−x,-y,-z) have a centroid separation of 3.686 (5) Å, with an interplanar spacing of 3.479 Å, corresponding to a plane slippage of 1.217 Å.

Related literature top

Studies of lead(II) complexes with N-donor ligands have been reported previosuly (Ali & Ali, 2002; Ali et al., 2005). We have recently determined the structure of a potential ligand containing multi-benzimidazole groups (Zhang et al. 2005).

For related literature, see: Adams et al. (1990); Byriel et al. (1992).

Experimental top

All reagents and solvents were used as obtained without further purification. Bis(benzimidazol-2-yl-methyl)amine (IDB) was prepared according to the method described by Adams et al. (1990). Compound (I) was synthesized by reaction of IDB (0.27 g, 1 mmol) and Pb(NO3)2(0.33 g, 1 mmol) in methanol (40 ml) at 333 K for 8 h. The resulting solution was filtered and yellow crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of the filtrate at room temperature after one week.

Refinement top

All the H atoms were located at their idealized positions [C—H(methylene) = 0.97 Å, N—H = 0.86 Å (imine) or 0.91 Å (amine), C—H(aromatic) = 0.93 Å], with the Uiso(H) value being set 1.2 times of their carrier atoms for all the H atoms. The largest peak in the final difference Fourier map of 2.79 e Å−3 is 1.00 Å from atom Pb1, and the deepest hole of 2.36 e Å−3 is 0.93 Å from atom Pb1.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of the three-dimensional network. Hydrogen bonding are shown as dashed lines.
[Bis(1H-benzimidazol-2-ylmethyl)amine-κ3N,N',N'']dinitratolead(II) top
Crystal data top
[Pb(NO3)2(C16H15N5)]Z = 2
Mr = 608.54F000 = 580
Triclinic, P1Dx = 2.056 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 8.9865 (4) ÅCell parameters from 6445 reflections
b = 10.4501 (5) Åθ = 2.4–28.1º
c = 11.3544 (5) ŵ = 8.63 mm−1
α = 98.296 (1)ºT = 292 (2) K
β = 102.842 (1)ºBlock, yellow
γ = 104.642 (1)º0.20 × 0.16 × 0.10 mm
V = 982.88 (8) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4007 independent reflections
Radiation source: fine focus sealed Siemens Mo tube3723 reflections with I > 2s(I)
Monochromator: graphiteRint = 0.037
T = 298(2) Kθmax = 26.5º
0.3° wide ω exposures scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		h = −11→11
Tmin = 0.277, Tmax = 0.479k = −13→13
9540 measured reflectionsl = −14→12
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.126  w = 1/[σ2(Fo2) + (0.0719P)2 + 3.4147P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
4007 reflectionsΔρmax = 2.79 e Å−3
271 parametersΔρmin = −2.36 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Pb(NO3)2(C16H15N5)]γ = 104.642 (1)º
Mr = 608.54V = 982.88 (8) Å3
Triclinic, P1Z = 2
a = 8.9865 (4) ÅMo Kα
b = 10.4501 (5) ŵ = 8.63 mm−1
c = 11.3544 (5) ÅT = 292 (2) K
α = 98.296 (1)º0.20 × 0.16 × 0.10 mm
β = 102.842 (1)º
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4007 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		3723 reflections with I > 2s(I)
Tmin = 0.277, Tmax = 0.479Rint = 0.037
9540 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045271 parameters
wR(F2) = 0.126H-atom parameters constrained
S = 1.12Δρmax = 2.79 e Å−3
4007 reflectionsΔρmin = −2.36 e Å−3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Pb10.35209 (3)0.12463 (3)0.37567 (3)0.03271 (13)
C10.1658 (10)0.3633 (8)0.4442 (8)0.0355 (17)
H1A0.20990.38550.53330.043*
H1B0.07480.39790.42500.043*
C20.2885 (9)0.4286 (8)0.3853 (8)0.0337 (17)
C30.4516 (11)0.5856 (8)0.3237 (8)0.0355 (17)
C40.5364 (13)0.7010 (10)0.2973 (9)0.050 (2)
H40.51500.78310.31570.060*
C50.6561 (16)0.6891 (13)0.2415 (12)0.066 (3)
H50.71790.76550.22300.080*
C60.6864 (15)0.5644 (11)0.2121 (11)0.060 (3)
H60.76630.56000.17320.073*
C70.6012 (12)0.4492 (9)0.2394 (10)0.049 (2)
H70.62330.36750.22110.059*
C80.4802 (10)0.4589 (9)0.2954 (8)0.0339 (17)
C9−0.0145 (8)0.1762 (8)0.2844 (7)0.0308 (15)
H9A−0.00120.24720.23800.037*
H9B−0.11710.16280.30270.037*
C10−0.0116 (8)0.0482 (9)0.2085 (7)0.0306 (16)
C11−0.0887 (9)−0.1419 (8)0.0670 (7)0.0312 (16)
C12−0.1692 (11)−0.2562 (9)−0.0261 (8)0.0408 (19)
H12−0.2747−0.2713−0.07010.049*
C13−0.0867 (13)−0.3455 (10)−0.0501 (9)0.049 (2)
H13−0.1389−0.4270−0.10670.058*
C140.0767 (12)−0.3150 (10)0.0100 (9)0.047 (2)
H140.1325−0.3736−0.01350.057*
C150.1570 (11)−0.2016 (10)0.1023 (8)0.043 (2)
H150.2636−0.18550.14410.052*
C160.0727 (9)−0.1120 (8)0.1309 (7)0.0292 (15)
N10.1139 (7)0.2177 (7)0.4010 (6)0.0323 (14)
H10.07350.18030.45910.039*
N20.3766 (8)0.3627 (7)0.3384 (7)0.0330 (14)
N30.3254 (8)0.5588 (6)0.3798 (6)0.0330 (14)
H30.28020.61640.40580.040*
N40.1155 (7)0.0067 (6)0.2194 (6)0.0278 (13)
N5−0.1368 (7)−0.0350 (7)0.1195 (6)0.0321 (14)
H5A−0.2303−0.02450.09830.039*
N60.5429 (8)0.0792 (7)0.1767 (7)0.0391 (16)
N70.2026 (10)−0.1607 (8)0.4578 (8)0.0439 (18)
O10.4232 (8)0.1232 (8)0.1732 (7)0.0541 (17)
O20.5790 (10)0.0167 (9)0.2572 (9)0.068 (2)
O30.6224 (8)0.1029 (8)0.1037 (7)0.0583 (19)
O40.1378 (9)−0.0720 (7)0.4771 (7)0.0521 (17)
O50.3208 (8)−0.1363 (8)0.4138 (7)0.0523 (17)
O60.1556 (12)−0.2715 (8)0.4820 (10)0.081 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.02497 (17)0.0335 (2)0.0372 (2)0.01051 (12)0.00101 (12)0.00779 (13)
C10.037 (4)0.024 (4)0.045 (5)0.009 (3)0.015 (4)0.001 (3)
C20.030 (3)0.031 (4)0.038 (4)0.010 (3)0.006 (3)0.004 (3)
C30.047 (4)0.032 (4)0.030 (4)0.013 (3)0.012 (3)0.008 (3)
C40.068 (6)0.045 (5)0.045 (5)0.019 (5)0.021 (5)0.022 (4)
C50.086 (8)0.063 (7)0.065 (7)0.017 (6)0.049 (7)0.029 (6)
C60.078 (7)0.049 (6)0.067 (7)0.017 (5)0.045 (6)0.017 (5)
C70.056 (5)0.033 (5)0.069 (7)0.010 (4)0.039 (5)0.013 (4)
C80.035 (4)0.035 (4)0.032 (4)0.009 (3)0.012 (3)0.006 (3)
C90.026 (3)0.030 (4)0.034 (4)0.009 (3)0.002 (3)0.005 (3)
C100.024 (3)0.046 (5)0.024 (4)0.013 (3)0.004 (3)0.012 (3)
C110.033 (4)0.040 (4)0.025 (4)0.013 (3)0.009 (3)0.016 (3)
C120.046 (5)0.040 (5)0.031 (4)0.010 (4)0.003 (4)0.011 (4)
C130.065 (6)0.041 (5)0.034 (5)0.007 (4)0.012 (4)0.009 (4)
C140.057 (5)0.046 (5)0.046 (5)0.024 (4)0.013 (4)0.016 (4)
C150.047 (5)0.055 (6)0.035 (5)0.031 (4)0.011 (4)0.009 (4)
C160.029 (3)0.033 (4)0.026 (4)0.007 (3)0.009 (3)0.009 (3)
N10.027 (3)0.037 (4)0.035 (4)0.011 (3)0.010 (3)0.012 (3)
N20.033 (3)0.032 (4)0.035 (4)0.009 (3)0.012 (3)0.005 (3)
N30.039 (3)0.023 (3)0.040 (4)0.013 (3)0.009 (3)0.007 (3)
N40.023 (3)0.030 (3)0.026 (3)0.009 (2)0.000 (2)−0.001 (3)
N50.021 (3)0.045 (4)0.028 (3)0.009 (3)0.003 (2)0.009 (3)
N60.026 (3)0.033 (4)0.054 (5)0.006 (3)0.009 (3)0.003 (3)
N70.048 (4)0.047 (5)0.048 (5)0.022 (4)0.022 (4)0.017 (4)
O10.042 (3)0.070 (5)0.064 (4)0.035 (3)0.019 (3)0.017 (4)
O20.061 (5)0.070 (5)0.089 (6)0.035 (4)0.022 (4)0.038 (5)
O30.048 (4)0.084 (5)0.061 (4)0.034 (4)0.029 (3)0.022 (4)
O40.070 (4)0.047 (4)0.063 (4)0.036 (3)0.035 (4)0.025 (3)
O50.047 (4)0.062 (4)0.067 (5)0.025 (3)0.033 (3)0.031 (4)
O60.103 (6)0.051 (5)0.134 (8)0.037 (4)0.092 (7)0.045 (5)
Geometric parameters (Å, °) top
Pb1—N42.357 (6)C9—H9A0.9700
Pb1—O12.519 (7)C9—H9B0.9700
Pb1—N22.546 (7)C10—N41.307 (9)
Pb1—N12.618 (6)C10—N51.338 (10)
Pb1—O42.988 (7)C11—C121.388 (12)
C1—N11.448 (10)C11—N51.399 (10)
C1—C21.486 (11)C11—C161.402 (10)
C1—H1A0.9700C12—C131.364 (13)
C1—H1B0.9700C12—H120.9300
C2—N21.320 (10)C13—C141.407 (14)
C2—N31.332 (10)C13—H130.9300
C3—C41.366 (13)C14—C151.377 (14)
C3—N31.407 (11)C14—H140.9300
C3—C81.418 (11)C15—C161.391 (11)
C4—C51.386 (15)C15—H150.9300
C4—H40.9300C16—N41.387 (10)
C5—C61.407 (16)N1—H10.9100
C5—H50.9300N3—H30.8600
C6—C71.370 (14)N5—H5A0.8600
C6—H60.9300N6—O31.221 (10)
C7—C81.393 (11)N6—O21.231 (11)
C7—H70.9300N6—O11.267 (9)
C8—N21.410 (11)N7—O61.221 (11)
C9—N11.474 (10)N7—O41.232 (9)
C9—C101.492 (11)N7—O51.257 (10)
N4—Pb1—O173.5 (2)N5—C10—C9124.0 (6)
N4—Pb1—N298.9 (2)C12—C11—N5132.5 (7)
O1—Pb1—N274.9 (2)C12—C11—C16123.2 (7)
N4—Pb1—N168.2 (2)N5—C11—C16104.4 (7)
O1—Pb1—N1117.3 (2)C13—C12—C11117.0 (8)
N2—Pb1—N164.6 (2)C13—C12—H12121.5
N4—Pb1—O470.6 (2)C11—C12—H12121.5
O1—Pb1—O4135.3 (2)C12—C13—C14120.5 (9)
N2—Pb1—O4136.02 (18)C12—C13—H13119.8
N1—Pb1—O472.04 (19)C14—C13—H13119.8
N1—C1—C2110.9 (6)C15—C14—C13122.4 (9)
N1—C1—H1A109.5C15—C14—H14118.8
C2—C1—H1A109.5C13—C14—H14118.8
N1—C1—H1B109.5C14—C15—C16117.6 (8)
C2—C1—H1B109.5C14—C15—H15121.2
H1A—C1—H1B108.1C16—C15—H15121.2
N2—C2—N3113.7 (7)N4—C16—C15132.0 (7)
N2—C2—C1122.4 (7)N4—C16—C11108.8 (6)
N3—C2—C1123.8 (7)C15—C16—C11119.1 (8)
C4—C3—N3132.5 (8)C1—N1—C9111.1 (6)
C4—C3—C8123.1 (8)C1—N1—Pb1111.7 (4)
N3—C3—C8104.4 (7)C9—N1—Pb1110.7 (4)
C3—C4—C5116.3 (9)C1—N1—H1107.7
C3—C4—H4121.8C9—N1—H1107.7
C5—C4—H4121.8Pb1—N1—H1107.7
C4—C5—C6121.6 (10)C2—N2—C8105.3 (7)
C4—C5—H5119.2C2—N2—Pb1116.9 (5)
C6—C5—H5119.2C8—N2—Pb1136.9 (5)
C7—C6—C5121.7 (9)C2—N3—C3107.8 (6)
C7—C6—H6119.2C2—N3—H3126.1
C5—C6—H6119.2C3—N3—H3126.1
C6—C7—C8117.6 (9)C10—N4—C16106.5 (6)
C6—C7—H7121.2C10—N4—Pb1120.6 (5)
C8—C7—H7121.2C16—N4—Pb1132.7 (5)
C7—C8—N2131.6 (8)C10—N5—C11107.9 (6)
C7—C8—C3119.6 (8)C10—N5—H5A126.0
N2—C8—C3108.7 (7)C11—N5—H5A126.0
N1—C9—C10110.8 (6)O3—N6—O2121.6 (7)
N1—C9—H9A109.5O3—N6—O1119.9 (8)
C10—C9—H9A109.5O2—N6—O1118.5 (8)
N1—C9—H9B109.5O6—N7—O4121.3 (8)
C10—C9—H9B109.5O6—N7—O5119.2 (7)
H9A—C9—H9B108.1O4—N7—O5119.4 (8)
N4—C10—N5112.3 (7)N6—O1—Pb1109.6 (6)
N4—C10—C9123.6 (7)N7—O4—Pb193.5 (5)
N1—C1—C2—N2−22.6 (12)C3—C8—N2—Pb1−166.3 (6)
N1—C1—C2—N3160.7 (8)N4—Pb1—N2—C280.7 (6)
N3—C3—C4—C5179.3 (11)O1—Pb1—N2—C2150.8 (6)
C8—C3—C4—C5−0.8 (15)N1—Pb1—N2—C220.0 (6)
C3—C4—C5—C61.0 (19)O4—Pb1—N2—C29.5 (8)
C4—C5—C6—C7−1(2)N4—Pb1—N2—C8−111.9 (8)
C5—C6—C7—C81.3 (19)O1—Pb1—N2—C8−41.8 (8)
C6—C7—C8—N2−177.4 (10)N1—Pb1—N2—C8−172.6 (9)
C6—C7—C8—C3−1.1 (16)O4—Pb1—N2—C8176.9 (7)
C4—C3—C8—C70.8 (15)N2—C2—N3—C3−0.1 (10)
N3—C3—C8—C7−179.2 (9)C1—C2—N3—C3176.9 (8)
C4—C3—C8—N2178.0 (9)C4—C3—N3—C2−178.7 (10)
N3—C3—C8—N2−2.1 (9)C8—C3—N3—C21.4 (9)
N1—C9—C10—N4−23.1 (11)N5—C10—N4—C160.4 (9)
N1—C9—C10—N5158.8 (7)C9—C10—N4—C16−177.8 (7)
N5—C11—C12—C13−176.5 (8)N5—C10—N4—Pb1−176.5 (5)
C16—C11—C12—C133.6 (12)C9—C10—N4—Pb15.2 (10)
C11—C12—C13—C14−5.6 (13)C15—C16—N4—C10−177.9 (9)
C12—C13—C14—C155.8 (15)C11—C16—N4—C10−1.2 (9)
C13—C14—C15—C16−3.4 (14)C15—C16—N4—Pb1−1.5 (13)
C14—C15—C16—N4177.7 (8)C11—C16—N4—Pb1175.3 (5)
C14—C15—C16—C111.2 (13)O1—Pb1—N4—C10−121.6 (6)
C12—C11—C16—N4−178.7 (7)N2—Pb1—N4—C10−50.4 (6)
N5—C11—C16—N41.4 (8)N1—Pb1—N4—C107.6 (6)
C12—C11—C16—C15−1.4 (12)O4—Pb1—N4—C1085.4 (6)
N5—C11—C16—C15178.6 (7)O1—Pb1—N4—C1662.3 (7)
C2—C1—N1—C9−85.2 (8)N2—Pb1—N4—C16133.6 (7)
C2—C1—N1—Pb138.9 (8)N1—Pb1—N4—C16−168.4 (7)
C10—C9—N1—C1151.1 (6)O4—Pb1—N4—C16−90.6 (7)
C10—C9—N1—Pb126.4 (7)N4—C10—N5—C110.4 (9)
N4—Pb1—N1—C1−142.9 (6)C9—C10—N5—C11178.7 (7)
O1—Pb1—N1—C1−86.3 (6)C12—C11—N5—C10178.9 (8)
N2—Pb1—N1—C1−31.0 (5)C16—C11—N5—C10−1.1 (8)
O4—Pb1—N1—C1141.4 (6)O3—N6—O1—Pb1−160.6 (7)
N4—Pb1—N1—C9−18.6 (5)O2—N6—O1—Pb117.1 (10)
O1—Pb1—N1—C938.1 (6)N4—Pb1—O1—N6−127.9 (6)
N2—Pb1—N1—C993.4 (5)N2—Pb1—O1—N6127.8 (6)
O4—Pb1—N1—C9−94.3 (5)N1—Pb1—O1—N6178.2 (5)
N3—C2—N2—C8−1.2 (10)O4—Pb1—O1—N6−90.2 (6)
C1—C2—N2—C8−178.3 (8)O6—N7—O4—Pb1−178.5 (10)
N3—C2—N2—Pb1169.9 (5)O5—N7—O4—Pb12.4 (9)
C1—C2—N2—Pb1−7.2 (10)N4—Pb1—O4—N794.9 (6)
C7—C8—N2—C2178.7 (10)O1—Pb1—O4—N756.6 (7)
C3—C8—N2—C22.1 (9)N2—Pb1—O4—N7177.5 (5)
C7—C8—N2—Pb110.4 (16)N1—Pb1—O4—N7167.5 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O6i0.862.042.895 (9)170
C4—H4···O2i0.932.583.332 (13)138
C4—H4···O5i0.932.523.248 (12)136
N3—H3···O5i0.862.503.165 (10)135
N5—H5A···O3ii0.862.112.876 (9)149
C12—H12···O1iii0.932.533.242 (11)133
N1—H1···O4iv0.912.273.099 (9)151
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) −x, −y, −z; (iv) −x, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O6i0.862.042.895 (9)170
C4—H4···O2i0.932.583.332 (13)138
C4—H4···O5i0.932.523.248 (12)136
N3—H3···O5i0.862.503.165 (10)135
N5—H5A···O3ii0.862.112.876 (9)149
C12—H12···O1iii0.932.533.242 (11)133
N1—H1···O4iv0.912.273.099 (9)151
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) −x, −y, −z; (iv) −x, −y, −z+1.
references
References top

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