Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025615/lh2392sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025615/lh2392Isup2.hkl |
CCDC reference: 654692
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.014 Å
- R factor = 0.045
- wR factor = 0.126
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O2
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.277 0.479 Tmin and Tmax expected: 0.204 0.422 RR = 1.197 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.17 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.88 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pb1 - O2 .. 5.52 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N7 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 14
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.881 Tmax scaled 0.422 Tmin scaled 0.244 PLAT794_ALERT_5_G Check Predicted Bond Valency for Pb1 (2) 2.21
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
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).
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.
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.
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.
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).
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.
[Pb(NO3)2(C16H15N5)] | Z = 2 |
Mr = 608.54 | F(000) = 580 |
Triclinic, P1 | Dx = 2.056 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9865 (4) Å | Cell parameters from 6445 reflections |
b = 10.4501 (5) Å | θ = 2.4–28.1° |
c = 11.3544 (5) Å | µ = 8.63 mm−1 |
α = 98.296 (1)° | T = 292 K |
β = 102.842 (1)° | Block, yellow |
γ = 104.642 (1)° | 0.20 × 0.16 × 0.10 mm |
V = 982.88 (8) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 4007 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 3723 reflections with I > 2s(I) |
Graphite monochromator | Rint = 0.037 |
0.3° wide ω exposures scans | θmax = 26.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −11→11 |
Tmin = 0.277, Tmax = 0.479 | k = −13→13 |
9540 measured reflections | l = −14→12 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0719P)2 + 3.4147P] where P = (Fo2 + 2Fc2)/3 |
4007 reflections | (Δ/σ)max < 0.001 |
271 parameters | Δρmax = 2.79 e Å−3 |
0 restraints | Δρmin = −2.37 e Å−3 |
[Pb(NO3)2(C16H15N5)] | γ = 104.642 (1)° |
Mr = 608.54 | V = 982.88 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.9865 (4) Å | Mo Kα radiation |
b = 10.4501 (5) Å | µ = 8.63 mm−1 |
c = 11.3544 (5) Å | T = 292 K |
α = 98.296 (1)° | 0.20 × 0.16 × 0.10 mm |
β = 102.842 (1)° |
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 = 0.479 | Rint = 0.037 |
9540 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.12 | Δρmax = 2.79 e Å−3 |
4007 reflections | Δρmin = −2.37 e Å−3 |
271 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Pb1 | 0.35209 (3) | 0.12463 (3) | 0.37567 (3) | 0.03271 (13) | |
C1 | 0.1658 (10) | 0.3633 (8) | 0.4442 (8) | 0.0355 (17) | |
H1A | 0.2099 | 0.3855 | 0.5333 | 0.043* | |
H1B | 0.0748 | 0.3979 | 0.4250 | 0.043* | |
C2 | 0.2885 (9) | 0.4286 (8) | 0.3853 (8) | 0.0337 (17) | |
C3 | 0.4516 (11) | 0.5856 (8) | 0.3237 (8) | 0.0355 (17) | |
C4 | 0.5364 (13) | 0.7010 (10) | 0.2973 (9) | 0.050 (2) | |
H4 | 0.5150 | 0.7831 | 0.3157 | 0.060* | |
C5 | 0.6561 (16) | 0.6891 (13) | 0.2415 (12) | 0.066 (3) | |
H5 | 0.7179 | 0.7655 | 0.2230 | 0.080* | |
C6 | 0.6864 (15) | 0.5644 (11) | 0.2121 (11) | 0.060 (3) | |
H6 | 0.7663 | 0.5600 | 0.1732 | 0.073* | |
C7 | 0.6012 (12) | 0.4492 (9) | 0.2394 (10) | 0.049 (2) | |
H7 | 0.6233 | 0.3675 | 0.2211 | 0.059* | |
C8 | 0.4802 (10) | 0.4589 (9) | 0.2954 (8) | 0.0339 (17) | |
C9 | −0.0145 (8) | 0.1762 (8) | 0.2844 (7) | 0.0308 (15) | |
H9A | −0.0012 | 0.2472 | 0.2380 | 0.037* | |
H9B | −0.1171 | 0.1628 | 0.3027 | 0.037* | |
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 | −0.0701 | 0.049* | |
C13 | −0.0867 (13) | −0.3455 (10) | −0.0501 (9) | 0.049 (2) | |
H13 | −0.1389 | −0.4270 | −0.1067 | 0.058* | |
C14 | 0.0767 (12) | −0.3150 (10) | 0.0100 (9) | 0.047 (2) | |
H14 | 0.1325 | −0.3736 | −0.0135 | 0.057* | |
C15 | 0.1570 (11) | −0.2016 (10) | 0.1023 (8) | 0.043 (2) | |
H15 | 0.2636 | −0.1855 | 0.1441 | 0.052* | |
C16 | 0.0727 (9) | −0.1120 (8) | 0.1309 (7) | 0.0292 (15) | |
N1 | 0.1139 (7) | 0.2177 (7) | 0.4010 (6) | 0.0323 (14) | |
H1 | 0.0735 | 0.1803 | 0.4591 | 0.039* | |
N2 | 0.3766 (8) | 0.3627 (7) | 0.3384 (7) | 0.0330 (14) | |
N3 | 0.3254 (8) | 0.5588 (6) | 0.3798 (6) | 0.0330 (14) | |
H3 | 0.2802 | 0.6164 | 0.4058 | 0.040* | |
N4 | 0.1155 (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 | −0.0245 | 0.0983 | 0.039* | |
N6 | 0.5429 (8) | 0.0792 (7) | 0.1767 (7) | 0.0391 (16) | |
N7 | 0.2026 (10) | −0.1607 (8) | 0.4578 (8) | 0.0439 (18) | |
O1 | 0.4232 (8) | 0.1232 (8) | 0.1732 (7) | 0.0541 (17) | |
O2 | 0.5790 (10) | 0.0167 (9) | 0.2572 (9) | 0.068 (2) | |
O3 | 0.6224 (8) | 0.1029 (8) | 0.1037 (7) | 0.0583 (19) | |
O4 | 0.1378 (9) | −0.0720 (7) | 0.4771 (7) | 0.0521 (17) | |
O5 | 0.3208 (8) | −0.1363 (8) | 0.4138 (7) | 0.0523 (17) | |
O6 | 0.1556 (12) | −0.2715 (8) | 0.4820 (10) | 0.081 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pb1 | 0.02497 (17) | 0.0335 (2) | 0.0372 (2) | 0.01051 (12) | 0.00101 (12) | 0.00779 (13) |
C1 | 0.037 (4) | 0.024 (4) | 0.045 (5) | 0.009 (3) | 0.015 (4) | 0.001 (3) |
C2 | 0.030 (3) | 0.031 (4) | 0.038 (4) | 0.010 (3) | 0.006 (3) | 0.004 (3) |
C3 | 0.047 (4) | 0.032 (4) | 0.030 (4) | 0.013 (3) | 0.012 (3) | 0.008 (3) |
C4 | 0.068 (6) | 0.045 (5) | 0.045 (5) | 0.019 (5) | 0.021 (5) | 0.022 (4) |
C5 | 0.086 (8) | 0.063 (7) | 0.065 (7) | 0.017 (6) | 0.049 (7) | 0.029 (6) |
C6 | 0.078 (7) | 0.049 (6) | 0.067 (7) | 0.017 (5) | 0.045 (6) | 0.017 (5) |
C7 | 0.056 (5) | 0.033 (5) | 0.069 (7) | 0.010 (4) | 0.039 (5) | 0.013 (4) |
C8 | 0.035 (4) | 0.035 (4) | 0.032 (4) | 0.009 (3) | 0.012 (3) | 0.006 (3) |
C9 | 0.026 (3) | 0.030 (4) | 0.034 (4) | 0.009 (3) | 0.002 (3) | 0.005 (3) |
C10 | 0.024 (3) | 0.046 (5) | 0.024 (4) | 0.013 (3) | 0.004 (3) | 0.012 (3) |
C11 | 0.033 (4) | 0.040 (4) | 0.025 (4) | 0.013 (3) | 0.009 (3) | 0.016 (3) |
C12 | 0.046 (5) | 0.040 (5) | 0.031 (4) | 0.010 (4) | 0.003 (4) | 0.011 (4) |
C13 | 0.065 (6) | 0.041 (5) | 0.034 (5) | 0.007 (4) | 0.012 (4) | 0.009 (4) |
C14 | 0.057 (5) | 0.046 (5) | 0.046 (5) | 0.024 (4) | 0.013 (4) | 0.016 (4) |
C15 | 0.047 (5) | 0.055 (6) | 0.035 (5) | 0.031 (4) | 0.011 (4) | 0.009 (4) |
C16 | 0.029 (3) | 0.033 (4) | 0.026 (4) | 0.007 (3) | 0.009 (3) | 0.009 (3) |
N1 | 0.027 (3) | 0.037 (4) | 0.035 (4) | 0.011 (3) | 0.010 (3) | 0.012 (3) |
N2 | 0.033 (3) | 0.032 (4) | 0.035 (4) | 0.009 (3) | 0.012 (3) | 0.005 (3) |
N3 | 0.039 (3) | 0.023 (3) | 0.040 (4) | 0.013 (3) | 0.009 (3) | 0.007 (3) |
N4 | 0.023 (3) | 0.030 (3) | 0.026 (3) | 0.009 (2) | 0.000 (2) | −0.001 (3) |
N5 | 0.021 (3) | 0.045 (4) | 0.028 (3) | 0.009 (3) | 0.003 (2) | 0.009 (3) |
N6 | 0.026 (3) | 0.033 (4) | 0.054 (5) | 0.006 (3) | 0.009 (3) | 0.003 (3) |
N7 | 0.048 (4) | 0.047 (5) | 0.048 (5) | 0.022 (4) | 0.022 (4) | 0.017 (4) |
O1 | 0.042 (3) | 0.070 (5) | 0.064 (4) | 0.035 (3) | 0.019 (3) | 0.017 (4) |
O2 | 0.061 (5) | 0.070 (5) | 0.089 (6) | 0.035 (4) | 0.022 (4) | 0.038 (5) |
O3 | 0.048 (4) | 0.084 (5) | 0.061 (4) | 0.034 (4) | 0.029 (3) | 0.022 (4) |
O4 | 0.070 (4) | 0.047 (4) | 0.063 (4) | 0.036 (3) | 0.035 (4) | 0.025 (3) |
O5 | 0.047 (4) | 0.062 (4) | 0.067 (5) | 0.025 (3) | 0.033 (3) | 0.031 (4) |
O6 | 0.103 (6) | 0.051 (5) | 0.134 (8) | 0.037 (4) | 0.092 (7) | 0.045 (5) |
Pb1—N4 | 2.357 (6) | C9—H9A | 0.9700 |
Pb1—O1 | 2.519 (7) | C9—H9B | 0.9700 |
Pb1—N2 | 2.546 (7) | C10—N4 | 1.307 (9) |
Pb1—N1 | 2.618 (6) | C10—N5 | 1.338 (10) |
Pb1—O4 | 2.988 (7) | C11—C12 | 1.388 (12) |
C1—N1 | 1.448 (10) | C11—N5 | 1.399 (10) |
C1—C2 | 1.486 (11) | C11—C16 | 1.402 (10) |
C1—H1A | 0.9700 | C12—C13 | 1.364 (13) |
C1—H1B | 0.9700 | C12—H12 | 0.9300 |
C2—N2 | 1.320 (10) | C13—C14 | 1.407 (14) |
C2—N3 | 1.332 (10) | C13—H13 | 0.9300 |
C3—C4 | 1.366 (13) | C14—C15 | 1.377 (14) |
C3—N3 | 1.407 (11) | C14—H14 | 0.9300 |
C3—C8 | 1.418 (11) | C15—C16 | 1.391 (11) |
C4—C5 | 1.386 (15) | C15—H15 | 0.9300 |
C4—H4 | 0.9300 | C16—N4 | 1.387 (10) |
C5—C6 | 1.407 (16) | N1—H1 | 0.9100 |
C5—H5 | 0.9300 | N3—H3 | 0.8600 |
C6—C7 | 1.370 (14) | N5—H5A | 0.8600 |
C6—H6 | 0.9300 | N6—O3 | 1.221 (10) |
C7—C8 | 1.393 (11) | N6—O2 | 1.231 (11) |
C7—H7 | 0.9300 | N6—O1 | 1.267 (9) |
C8—N2 | 1.410 (11) | N7—O6 | 1.221 (11) |
C9—N1 | 1.474 (10) | N7—O4 | 1.232 (9) |
C9—C10 | 1.492 (11) | N7—O5 | 1.257 (10) |
N4—Pb1—O1 | 73.5 (2) | N5—C10—C9 | 124.0 (6) |
N4—Pb1—N2 | 98.9 (2) | C12—C11—N5 | 132.5 (7) |
O1—Pb1—N2 | 74.9 (2) | C12—C11—C16 | 123.2 (7) |
N4—Pb1—N1 | 68.2 (2) | N5—C11—C16 | 104.4 (7) |
O1—Pb1—N1 | 117.3 (2) | C13—C12—C11 | 117.0 (8) |
N2—Pb1—N1 | 64.6 (2) | C13—C12—H12 | 121.5 |
N4—Pb1—O4 | 70.6 (2) | C11—C12—H12 | 121.5 |
O1—Pb1—O4 | 135.3 (2) | C12—C13—C14 | 120.5 (9) |
N2—Pb1—O4 | 136.02 (18) | C12—C13—H13 | 119.8 |
N1—Pb1—O4 | 72.04 (19) | C14—C13—H13 | 119.8 |
N1—C1—C2 | 110.9 (6) | C15—C14—C13 | 122.4 (9) |
N1—C1—H1A | 109.5 | C15—C14—H14 | 118.8 |
C2—C1—H1A | 109.5 | C13—C14—H14 | 118.8 |
N1—C1—H1B | 109.5 | C14—C15—C16 | 117.6 (8) |
C2—C1—H1B | 109.5 | C14—C15—H15 | 121.2 |
H1A—C1—H1B | 108.1 | C16—C15—H15 | 121.2 |
N2—C2—N3 | 113.7 (7) | N4—C16—C15 | 132.0 (7) |
N2—C2—C1 | 122.4 (7) | N4—C16—C11 | 108.8 (6) |
N3—C2—C1 | 123.8 (7) | C15—C16—C11 | 119.1 (8) |
C4—C3—N3 | 132.5 (8) | C1—N1—C9 | 111.1 (6) |
C4—C3—C8 | 123.1 (8) | C1—N1—Pb1 | 111.7 (4) |
N3—C3—C8 | 104.4 (7) | C9—N1—Pb1 | 110.7 (4) |
C3—C4—C5 | 116.3 (9) | C1—N1—H1 | 107.7 |
C3—C4—H4 | 121.8 | C9—N1—H1 | 107.7 |
C5—C4—H4 | 121.8 | Pb1—N1—H1 | 107.7 |
C4—C5—C6 | 121.6 (10) | C2—N2—C8 | 105.3 (7) |
C4—C5—H5 | 119.2 | C2—N2—Pb1 | 116.9 (5) |
C6—C5—H5 | 119.2 | C8—N2—Pb1 | 136.9 (5) |
C7—C6—C5 | 121.7 (9) | C2—N3—C3 | 107.8 (6) |
C7—C6—H6 | 119.2 | C2—N3—H3 | 126.1 |
C5—C6—H6 | 119.2 | C3—N3—H3 | 126.1 |
C6—C7—C8 | 117.6 (9) | C10—N4—C16 | 106.5 (6) |
C6—C7—H7 | 121.2 | C10—N4—Pb1 | 120.6 (5) |
C8—C7—H7 | 121.2 | C16—N4—Pb1 | 132.7 (5) |
C7—C8—N2 | 131.6 (8) | C10—N5—C11 | 107.9 (6) |
C7—C8—C3 | 119.6 (8) | C10—N5—H5A | 126.0 |
N2—C8—C3 | 108.7 (7) | C11—N5—H5A | 126.0 |
N1—C9—C10 | 110.8 (6) | O3—N6—O2 | 121.6 (7) |
N1—C9—H9A | 109.5 | O3—N6—O1 | 119.9 (8) |
C10—C9—H9A | 109.5 | O2—N6—O1 | 118.5 (8) |
N1—C9—H9B | 109.5 | O6—N7—O4 | 121.3 (8) |
C10—C9—H9B | 109.5 | O6—N7—O5 | 119.2 (7) |
H9A—C9—H9B | 108.1 | O4—N7—O5 | 119.4 (8) |
N4—C10—N5 | 112.3 (7) | N6—O1—Pb1 | 109.6 (6) |
N4—C10—C9 | 123.6 (7) | N7—O4—Pb1 | 93.5 (5) |
N1—C1—C2—N2 | −22.6 (12) | C3—C8—N2—Pb1 | −166.3 (6) |
N1—C1—C2—N3 | 160.7 (8) | N4—Pb1—N2—C2 | 80.7 (6) |
N3—C3—C4—C5 | 179.3 (11) | O1—Pb1—N2—C2 | 150.8 (6) |
C8—C3—C4—C5 | −0.8 (15) | N1—Pb1—N2—C2 | 20.0 (6) |
C3—C4—C5—C6 | 1.0 (19) | O4—Pb1—N2—C2 | 9.5 (8) |
C4—C5—C6—C7 | −1 (2) | N4—Pb1—N2—C8 | −111.9 (8) |
C5—C6—C7—C8 | 1.3 (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—C8 | 176.9 (7) |
C4—C3—C8—C7 | 0.8 (15) | N2—C2—N3—C3 | −0.1 (10) |
N3—C3—C8—C7 | −179.2 (9) | C1—C2—N3—C3 | 176.9 (8) |
C4—C3—C8—N2 | 178.0 (9) | C4—C3—N3—C2 | −178.7 (10) |
N3—C3—C8—N2 | −2.1 (9) | C8—C3—N3—C2 | 1.4 (9) |
N1—C9—C10—N4 | −23.1 (11) | N5—C10—N4—C16 | 0.4 (9) |
N1—C9—C10—N5 | 158.8 (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—C13 | 3.6 (12) | C9—C10—N4—Pb1 | 5.2 (10) |
C11—C12—C13—C14 | −5.6 (13) | C15—C16—N4—C10 | −177.9 (9) |
C12—C13—C14—C15 | 5.8 (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—N4 | 177.7 (8) | C11—C16—N4—Pb1 | 175.3 (5) |
C14—C15—C16—C11 | 1.2 (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—N4 | 1.4 (8) | N1—Pb1—N4—C10 | 7.6 (6) |
C12—C11—C16—C15 | −1.4 (12) | O4—Pb1—N4—C10 | 85.4 (6) |
N5—C11—C16—C15 | 178.6 (7) | O1—Pb1—N4—C16 | 62.3 (7) |
C2—C1—N1—C9 | −85.2 (8) | N2—Pb1—N4—C16 | 133.6 (7) |
C2—C1—N1—Pb1 | 38.9 (8) | N1—Pb1—N4—C16 | −168.4 (7) |
C10—C9—N1—C1 | 151.1 (6) | O4—Pb1—N4—C16 | −90.6 (7) |
C10—C9—N1—Pb1 | 26.4 (7) | N4—C10—N5—C11 | 0.4 (9) |
N4—Pb1—N1—C1 | −142.9 (6) | C9—C10—N5—C11 | 178.7 (7) |
O1—Pb1—N1—C1 | −86.3 (6) | C12—C11—N5—C10 | 178.9 (8) |
N2—Pb1—N1—C1 | −31.0 (5) | C16—C11—N5—C10 | −1.1 (8) |
O4—Pb1—N1—C1 | 141.4 (6) | O3—N6—O1—Pb1 | −160.6 (7) |
N4—Pb1—N1—C9 | −18.6 (5) | O2—N6—O1—Pb1 | 17.1 (10) |
O1—Pb1—N1—C9 | 38.1 (6) | N4—Pb1—O1—N6 | −127.9 (6) |
N2—Pb1—N1—C9 | 93.4 (5) | N2—Pb1—O1—N6 | 127.8 (6) |
O4—Pb1—N1—C9 | −94.3 (5) | N1—Pb1—O1—N6 | 178.2 (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—Pb1 | 169.9 (5) | O5—N7—O4—Pb1 | 2.4 (9) |
C1—C2—N2—Pb1 | −7.2 (10) | N4—Pb1—O4—N7 | 94.9 (6) |
C7—C8—N2—C2 | 178.7 (10) | O1—Pb1—O4—N7 | 56.6 (7) |
C3—C8—N2—C2 | 2.1 (9) | N2—Pb1—O4—N7 | 177.5 (5) |
C7—C8—N2—Pb1 | 10.4 (16) | N1—Pb1—O4—N7 | 167.5 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O6i | 0.86 | 2.04 | 2.895 (9) | 170 |
C4—H4···O2i | 0.93 | 2.58 | 3.332 (13) | 138 |
C4—H4···O5i | 0.93 | 2.52 | 3.248 (12) | 136 |
N3—H3···O5i | 0.86 | 2.50 | 3.165 (10) | 135 |
N5—H5A···O3ii | 0.86 | 2.11 | 2.876 (9) | 149 |
C12—H12···O1iii | 0.93 | 2.53 | 3.242 (11) | 133 |
N1—H1···O4iv | 0.91 | 2.27 | 3.099 (9) | 151 |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) −x, −y, −z; (iv) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Pb(NO3)2(C16H15N5)] |
Mr | 608.54 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 292 |
a, b, c (Å) | 8.9865 (4), 10.4501 (5), 11.3544 (5) |
α, β, γ (°) | 98.296 (1), 102.842 (1), 104.642 (1) |
V (Å3) | 982.88 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 8.63 |
Crystal size (mm) | 0.20 × 0.16 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.277, 0.479 |
No. of measured, independent and observed [I > 2s(I)] reflections | 9540, 4007, 3723 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.126, 1.12 |
No. of reflections | 4007 |
No. of parameters | 271 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.79, −2.37 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O6i | 0.86 | 2.04 | 2.895 (9) | 170.3 |
C4—H4···O2i | 0.93 | 2.58 | 3.332 (13) | 138.3 |
C4—H4···O5i | 0.93 | 2.52 | 3.248 (12) | 135.7 |
N3—H3···O5i | 0.86 | 2.50 | 3.165 (10) | 134.5 |
N5—H5A···O3ii | 0.86 | 2.11 | 2.876 (9) | 148.7 |
C12—H12···O1iii | 0.93 | 2.53 | 3.242 (11) | 133.3 |
N1—H1···O4iv | 0.91 | 2.27 | 3.099 (9) | 150.6 |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) −x, −y, −z; (iv) −x, −y, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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.