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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 π–π inter­actions, with ring-centroid separations of 3.578 (5) and 3.686 (5) Å, leading to a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025615/lh2392sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025615/lh2392Isup2.hkl
Contains datablock I

CCDC reference: 654692

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](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

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 [CH(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.

Structure description 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.

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).

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 = 608.54F(000) = 580
Triclinic, P1Dx = 2.056 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9865 (4) ÅCell parameters from 6445 reflections
b = 10.4501 (5) Åθ = 2.4–28.1°
c = 11.3544 (5) ŵ = 8.63 mm1
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
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)
Graphite monochromatorRint = 0.037
0.3° wide ω exposures scansθmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1111
Tmin = 0.277, Tmax = 0.479k = 1313
9540 measured reflectionsl = 1412
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-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 parametersΔρmax = 2.79 e Å3
0 restraintsΔρmin = 2.37 e Å3
Crystal data top
[Pb(NO3)2(C16H15N5)]γ = 104.642 (1)°
Mr = 608.54V = 982.88 (8) Å3
Triclinic, P1Z = 2
a = 8.9865 (4) ÅMo Kα radiation
b = 10.4501 (5) ŵ = 8.63 mm1
c = 11.3544 (5) ÅT = 292 K
α = 98.296 (1)°0.20 × 0.16 × 0.10 mm
β = 102.842 (1)°
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)] = 0.0450 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.12Δρmax = 2.79 e Å3
4007 reflectionsΔρmin = 2.37 e Å3
271 parameters
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)
C90.0145 (8)0.1762 (8)0.2844 (7)0.0308 (15)
H9A0.00120.24720.23800.037*
H9B0.11710.16280.30270.037*
C100.0116 (8)0.0482 (9)0.2085 (7)0.0306 (16)
C110.0887 (9)0.1419 (8)0.0670 (7)0.0312 (16)
C120.1692 (11)0.2562 (9)0.0261 (8)0.0408 (19)
H120.27470.27130.07010.049*
C130.0867 (13)0.3455 (10)0.0501 (9)0.049 (2)
H130.13890.42700.10670.058*
C140.0767 (12)0.3150 (10)0.0100 (9)0.047 (2)
H140.13250.37360.01350.057*
C150.1570 (11)0.2016 (10)0.1023 (8)0.043 (2)
H150.26360.18550.14410.052*
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)
N50.1368 (7)0.0350 (7)0.1195 (6)0.0321 (14)
H5A0.23030.02450.09830.039*
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, º) 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—N222.6 (12)C3—C8—N2—Pb1166.3 (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—C50.8 (15)N1—Pb1—N2—C220.0 (6)
C3—C4—C5—C61.0 (19)O4—Pb1—N2—C29.5 (8)
C4—C5—C6—C71 (2)N4—Pb1—N2—C8111.9 (8)
C5—C6—C7—C81.3 (19)O1—Pb1—N2—C841.8 (8)
C6—C7—C8—N2177.4 (10)N1—Pb1—N2—C8172.6 (9)
C6—C7—C8—C31.1 (16)O4—Pb1—N2—C8176.9 (7)
C4—C3—C8—C70.8 (15)N2—C2—N3—C30.1 (10)
N3—C3—C8—C7179.2 (9)C1—C2—N3—C3176.9 (8)
C4—C3—C8—N2178.0 (9)C4—C3—N3—C2178.7 (10)
N3—C3—C8—N22.1 (9)C8—C3—N3—C21.4 (9)
N1—C9—C10—N423.1 (11)N5—C10—N4—C160.4 (9)
N1—C9—C10—N5158.8 (7)C9—C10—N4—C16177.8 (7)
N5—C11—C12—C13176.5 (8)N5—C10—N4—Pb1176.5 (5)
C16—C11—C12—C133.6 (12)C9—C10—N4—Pb15.2 (10)
C11—C12—C13—C145.6 (13)C15—C16—N4—C10177.9 (9)
C12—C13—C14—C155.8 (15)C11—C16—N4—C101.2 (9)
C13—C14—C15—C163.4 (14)C15—C16—N4—Pb11.5 (13)
C14—C15—C16—N4177.7 (8)C11—C16—N4—Pb1175.3 (5)
C14—C15—C16—C111.2 (13)O1—Pb1—N4—C10121.6 (6)
C12—C11—C16—N4178.7 (7)N2—Pb1—N4—C1050.4 (6)
N5—C11—C16—N41.4 (8)N1—Pb1—N4—C107.6 (6)
C12—C11—C16—C151.4 (12)O4—Pb1—N4—C1085.4 (6)
N5—C11—C16—C15178.6 (7)O1—Pb1—N4—C1662.3 (7)
C2—C1—N1—C985.2 (8)N2—Pb1—N4—C16133.6 (7)
C2—C1—N1—Pb138.9 (8)N1—Pb1—N4—C16168.4 (7)
C10—C9—N1—C1151.1 (6)O4—Pb1—N4—C1690.6 (7)
C10—C9—N1—Pb126.4 (7)N4—C10—N5—C110.4 (9)
N4—Pb1—N1—C1142.9 (6)C9—C10—N5—C11178.7 (7)
O1—Pb1—N1—C186.3 (6)C12—C11—N5—C10178.9 (8)
N2—Pb1—N1—C131.0 (5)C16—C11—N5—C101.1 (8)
O4—Pb1—N1—C1141.4 (6)O3—N6—O1—Pb1160.6 (7)
N4—Pb1—N1—C918.6 (5)O2—N6—O1—Pb117.1 (10)
O1—Pb1—N1—C938.1 (6)N4—Pb1—O1—N6127.9 (6)
N2—Pb1—N1—C993.4 (5)N2—Pb1—O1—N6127.8 (6)
O4—Pb1—N1—C994.3 (5)N1—Pb1—O1—N6178.2 (5)
N3—C2—N2—C81.2 (10)O4—Pb1—O1—N690.2 (6)
C1—C2—N2—C8178.3 (8)O6—N7—O4—Pb1178.5 (10)
N3—C2—N2—Pb1169.9 (5)O5—N7—O4—Pb12.4 (9)
C1—C2—N2—Pb17.2 (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, º) 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) x1, y, z; (iii) x, y, z; (iv) x, y, z+1.

Experimental details

Crystal data
Chemical formula[Pb(NO3)2(C16H15N5)]
Mr608.54
Crystal system, space groupTriclinic, 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)
V3)982.88 (8)
Z2
Radiation typeMo Kα
µ (mm1)8.63
Crystal size (mm)0.20 × 0.16 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.277, 0.479
No. of measured, independent and
observed [I > 2s(I)] reflections
9540, 4007, 3723
Rint0.037
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.126, 1.12
No. of reflections4007
No. of parameters271
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.79, 2.37

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O6i0.862.042.895 (9)170.3
C4—H4···O2i0.932.583.332 (13)138.3
C4—H4···O5i0.932.523.248 (12)135.7
N3—H3···O5i0.862.503.165 (10)134.5
N5—H5A···O3ii0.862.112.876 (9)148.7
C12—H12···O1iii0.932.533.242 (11)133.3
N1—H1···O4iv0.912.273.099 (9)150.6
Symmetry codes: (i) x, y+1, z; (ii) x1, y, z; (iii) x, y, z; (iv) x, y, z+1.
 

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