metal-organic compounds
Bis(imidazo[4,5-f][1,10]phenanthroline)dinitratolead(II)
aSchool of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, People's Republic of China, and bDepartment of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China
*Correspondence e-mail: guangbochejl@yahoo.com
In the title compound, [Pb(NO3)2(C13H8N4)2], the PbII atom (site symmetry 2) is hexacoordinated by four N atoms from two N,N′-bidentate imidazo[4,5-f][1,10]phenanthroline (L) ligands and two O atoms from two weakly coordinated nitrate ions [Pb—O = 2.872 (5) Å] in an irregular arrangement, which may be ascribed to the stereochemically active lone pair of electrons on the metal ion. In the crystal, intermolecular bifurcated N—H⋯(O,O) hydrogen bonds connect the molecules into chains propagating along [100]. Adjacent chains interact by strong aromatic π–π stacking interactions, with a centroid–centroid distance of 3.483 (2) Å.
Related literature
For the ligand synthesis, see: Steck & Day (1943). For background, see: Che et al. (2006, 2008); Thomas et al. (2008); Xu et al. (2008).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808041317/hb2871sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808041317/hb2871Isup2.hkl
The L ligand was synthesized according to the literature method of Steck & Day (1943). A mixture of Pb(NO3)2 (0.5 mmol) and the ligand (1 mmol) was dissolved in 15 ml distilled water, then followed by addition of NaOH until the pH value of the system approximately 6.0. Finally the resulting solution was sealed into a 23 ml Teflon-lined stainless steel autoclave and heated at 413 K for 3 d under autogenous pressure. The reaction autoclave slowly cooled to room temperature, yielding yellow block-like crystals of (I) in 62% yield based on Pb.
All H atoms on C atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H)= 1.2Ueq(C). The hydrogen atoms of water molecules were located from difference Fourier maps and their positions and Uiso values were refined freely.
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXS97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Pb(NO3)2(C13H8N4)2] | F(000) = 1488 |
Mr = 771.68 | Dx = 2.111 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3904 reflections |
a = 19.203 (4) Å | θ = 2.2–26.1° |
b = 7.3948 (15) Å | µ = 7.02 mm−1 |
c = 17.392 (4) Å | T = 292 K |
β = 100.48 (3)° | Block, yellow |
V = 2428.5 (8) Å3 | 0.56 × 0.22 × 0.11 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 2402 independent reflections |
Radiation source: fine-focus sealed tube | 2170 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
ω scans | θmax = 26.1°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −23→23 |
Tmin = 0.165, Tmax = 0.453 | k = −9→9 |
10060 measured reflections | l = −20→21 |
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)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.064 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0304P)2] where P = (Fo2 + 2Fc2)/3 |
2402 reflections | (Δ/σ)max = 0.005 |
195 parameters | Δρmax = 0.89 e Å−3 |
0 restraints | Δρmin = −0.63 e Å−3 |
[Pb(NO3)2(C13H8N4)2] | V = 2428.5 (8) Å3 |
Mr = 771.68 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 19.203 (4) Å | µ = 7.02 mm−1 |
b = 7.3948 (15) Å | T = 292 K |
c = 17.392 (4) Å | 0.56 × 0.22 × 0.11 mm |
β = 100.48 (3)° |
Bruker SMART CCD diffractometer | 2402 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 2170 reflections with I > 2σ(I) |
Tmin = 0.165, Tmax = 0.453 | Rint = 0.049 |
10060 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.064 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.89 e Å−3 |
2402 reflections | Δρmin = −0.63 e Å−3 |
195 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 | ||
C1 | 0.3676 (2) | −0.2885 (6) | 0.1841 (2) | 0.0361 (10) | |
H1 | 0.3576 | −0.2644 | 0.2334 | 0.043* | |
C2 | 0.3181 (3) | −0.3843 (7) | 0.1316 (3) | 0.0472 (12) | |
H2 | 0.2772 | −0.4283 | 0.1466 | 0.057* | |
C3 | 0.3303 (2) | −0.4130 (6) | 0.0577 (3) | 0.0411 (11) | |
H3 | 0.2973 | −0.4749 | 0.0214 | 0.049* | |
C4 | 0.3927 (2) | −0.3486 (5) | 0.0372 (2) | 0.0270 (9) | |
C5 | 0.4423 (2) | −0.2606 (5) | 0.0951 (2) | 0.0242 (8) | |
C6 | 0.5099 (2) | −0.1997 (5) | 0.0783 (2) | 0.0242 (8) | |
C7 | 0.6190 (2) | −0.0678 (6) | 0.1228 (3) | 0.0329 (9) | |
H7 | 0.6505 | −0.0117 | 0.1627 | 0.040* | |
C8 | 0.6394 (2) | −0.0921 (6) | 0.0507 (2) | 0.0354 (10) | |
H8 | 0.6845 | −0.0580 | 0.0439 | 0.043* | |
C9 | 0.4103 (2) | −0.3613 (5) | −0.0386 (2) | 0.0284 (9) | |
C10 | 0.5268 (2) | −0.2217 (5) | 0.0028 (2) | 0.0251 (8) | |
C11 | 0.4729 (2) | −0.2999 (5) | −0.0565 (2) | 0.0272 (9) | |
C12 | 0.4129 (3) | −0.3952 (6) | −0.1631 (2) | 0.0386 (11) | |
H12 | 0.3985 | −0.4253 | −0.2155 | 0.046* | |
C13 | 0.5931 (2) | −0.1660 (5) | −0.0100 (2) | 0.0296 (9) | |
H13 | 0.6055 | −0.1790 | −0.0590 | 0.035* | |
N5 | 0.2959 (2) | 0.1066 (5) | 0.1716 (2) | 0.0387 (9) | |
O2 | 0.2564 (2) | 0.0783 (8) | 0.2184 (3) | 0.0874 (14) | |
N1 | 0.42843 (17) | −0.2294 (4) | 0.16763 (18) | 0.0268 (7) | |
N2 | 0.55658 (17) | −0.1214 (4) | 0.13726 (18) | 0.0262 (7) | |
N3 | 0.3723 (2) | −0.4235 (5) | −0.1083 (2) | 0.0359 (8) | |
H3A | 0.3307 | −0.4711 | −0.1156 | 0.043* | |
N4 | 0.4751 (2) | −0.3210 (4) | −0.13538 (18) | 0.0341 (8) | |
O1 | 0.35914 (17) | 0.1449 (5) | 0.19411 (19) | 0.0508 (9) | |
O3 | 0.2706 (2) | 0.0901 (7) | 0.1014 (2) | 0.0747 (12) | |
Pb | 0.5000 | 0.01345 (3) | 0.2500 | 0.02722 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.034 (3) | 0.047 (2) | 0.030 (2) | −0.005 (2) | 0.013 (2) | 0.0003 (19) |
C2 | 0.032 (3) | 0.068 (3) | 0.044 (3) | −0.018 (2) | 0.013 (2) | −0.006 (2) |
C3 | 0.032 (3) | 0.055 (3) | 0.035 (3) | −0.017 (2) | 0.003 (2) | −0.008 (2) |
C4 | 0.024 (2) | 0.0303 (19) | 0.026 (2) | −0.0021 (16) | 0.0025 (17) | 0.0008 (16) |
C5 | 0.022 (2) | 0.0264 (18) | 0.024 (2) | 0.0013 (16) | 0.0046 (17) | 0.0018 (15) |
C6 | 0.024 (2) | 0.0247 (18) | 0.023 (2) | 0.0014 (15) | 0.0024 (17) | 0.0016 (15) |
C7 | 0.025 (2) | 0.041 (2) | 0.031 (2) | −0.0063 (19) | 0.0020 (19) | −0.0061 (18) |
C8 | 0.027 (3) | 0.046 (2) | 0.035 (3) | −0.005 (2) | 0.010 (2) | 0.0001 (19) |
C9 | 0.026 (2) | 0.032 (2) | 0.025 (2) | −0.0007 (17) | −0.0023 (18) | −0.0004 (16) |
C10 | 0.023 (2) | 0.0264 (19) | 0.025 (2) | 0.0021 (17) | 0.0033 (16) | 0.0028 (15) |
C11 | 0.032 (2) | 0.0283 (19) | 0.021 (2) | 0.0018 (17) | 0.0034 (17) | 0.0013 (15) |
C12 | 0.047 (3) | 0.043 (2) | 0.022 (2) | 0.000 (2) | −0.003 (2) | −0.0042 (18) |
C13 | 0.030 (2) | 0.041 (2) | 0.020 (2) | 0.0006 (18) | 0.0111 (18) | −0.0019 (16) |
N5 | 0.035 (2) | 0.051 (2) | 0.030 (2) | 0.0030 (18) | 0.0059 (18) | −0.0036 (16) |
O2 | 0.048 (3) | 0.171 (4) | 0.049 (3) | −0.009 (3) | 0.024 (2) | 0.008 (3) |
N1 | 0.0184 (18) | 0.0355 (17) | 0.0273 (18) | −0.0007 (14) | 0.0065 (14) | 0.0000 (13) |
N2 | 0.0235 (19) | 0.0331 (17) | 0.0217 (17) | −0.0045 (14) | 0.0031 (14) | −0.0022 (13) |
N3 | 0.031 (2) | 0.0431 (19) | 0.032 (2) | −0.0073 (17) | 0.0007 (17) | −0.0029 (16) |
N4 | 0.041 (2) | 0.0406 (19) | 0.0202 (18) | −0.0029 (17) | 0.0032 (16) | −0.0022 (14) |
O1 | 0.0265 (19) | 0.068 (2) | 0.053 (2) | −0.0076 (16) | −0.0049 (16) | −0.0099 (17) |
O3 | 0.054 (3) | 0.133 (4) | 0.034 (2) | −0.016 (3) | −0.0015 (19) | −0.009 (2) |
Pb | 0.02505 (15) | 0.03545 (14) | 0.02129 (13) | 0.000 | 0.00458 (9) | 0.000 |
C1—N1 | 1.327 (5) | C9—N3 | 1.376 (5) |
C1—C2 | 1.387 (6) | C10—C13 | 1.393 (6) |
C1—H1 | 0.9300 | C10—C11 | 1.442 (5) |
C2—C3 | 1.364 (6) | C11—N4 | 1.390 (5) |
C2—H2 | 0.9300 | C12—N4 | 1.323 (5) |
C3—C4 | 1.396 (6) | C12—N3 | 1.353 (6) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.413 (5) | C13—H13 | 0.9300 |
C4—C9 | 1.423 (5) | N5—O2 | 1.227 (5) |
C5—N1 | 1.355 (5) | N5—O3 | 1.235 (5) |
C5—C6 | 1.453 (5) | N5—O1 | 1.239 (5) |
C6—N2 | 1.362 (5) | Pb—N1 | 2.540 (3) |
C6—C10 | 1.418 (5) | Pb—N2 | 2.606 (3) |
C7—N2 | 1.329 (5) | Pb—O1 | 2.872 (5) |
C7—C8 | 1.392 (6) | N3—H3A | 0.8600 |
C7—H7 | 0.9300 | Pb—N1i | 2.540 (3) |
C8—C13 | 1.365 (6) | Pb—N2i | 2.606 (3) |
C8—H8 | 0.9300 | O1—Pbi | 2.872 (5) |
C9—C11 | 1.372 (6) | ||
N1—C1—C2 | 123.5 (4) | C9—C11—N4 | 111.8 (4) |
N1—C1—H1 | 118.3 | C9—C11—C10 | 121.0 (3) |
C2—C1—H1 | 118.3 | N4—C11—C10 | 127.1 (4) |
C3—C2—C1 | 119.0 (4) | N4—C12—N3 | 113.9 (4) |
C3—C2—H2 | 120.5 | N4—C12—H12 | 123.0 |
C1—C2—H2 | 120.5 | N3—C12—H12 | 123.0 |
C2—C3—C4 | 119.4 (4) | C8—C13—C10 | 118.7 (4) |
C2—C3—H3 | 120.3 | C8—C13—H13 | 120.6 |
C4—C3—H3 | 120.3 | C10—C13—H13 | 120.6 |
C3—C4—C5 | 118.3 (4) | O2—N5—O3 | 117.3 (4) |
C3—C4—C9 | 125.0 (4) | O2—N5—O1 | 121.2 (4) |
C5—C4—C9 | 116.6 (4) | O3—N5—O1 | 121.4 (4) |
N1—C5—C4 | 121.4 (3) | C1—N1—C5 | 118.4 (3) |
N1—C5—C6 | 118.0 (3) | C1—N1—Pb | 121.2 (3) |
C4—C5—C6 | 120.7 (3) | C5—N1—Pb | 117.9 (2) |
N2—C6—C10 | 121.1 (4) | C7—N2—C6 | 118.5 (3) |
N2—C6—C5 | 118.0 (3) | C7—N2—Pb | 122.8 (3) |
C10—C6—C5 | 120.9 (3) | C6—N2—Pb | 115.0 (2) |
N2—C7—C8 | 122.9 (4) | C12—N3—C9 | 106.7 (4) |
N2—C7—H7 | 118.6 | C12—N3—H3A | 126.7 |
C8—C7—H7 | 118.6 | C9—N3—H3A | 126.7 |
C13—C8—C7 | 119.9 (4) | C12—N4—C11 | 102.6 (4) |
C13—C8—H8 | 120.1 | N1—Pb—N1i | 90.01 (14) |
C7—C8—H8 | 120.1 | N1—Pb—N2i | 84.09 (10) |
C11—C9—N3 | 105.0 (3) | N1i—Pb—N2i | 64.03 (10) |
C11—C9—C4 | 123.6 (4) | N1—Pb—N2 | 64.03 (10) |
N3—C9—C4 | 131.4 (4) | N1i—Pb—N2 | 84.09 (10) |
C13—C10—C6 | 118.9 (4) | N2i—Pb—N2 | 135.02 (14) |
C13—C10—C11 | 124.2 (3) | O1—Pb—N1 | 70.65 (10) |
C6—C10—C11 | 116.9 (4) | O1—Pb—N2 | 111.75 (10) |
N1—C1—C2—C3 | −3.2 (7) | C11—C10—C13—C8 | 179.3 (4) |
C1—C2—C3—C4 | 1.2 (7) | C2—C1—N1—C5 | 1.6 (6) |
C2—C3—C4—C5 | 2.1 (7) | C2—C1—N1—Pb | 163.1 (4) |
C2—C3—C4—C9 | −176.7 (4) | C4—C5—N1—C1 | 2.0 (5) |
C3—C4—C5—N1 | −3.8 (6) | C6—C5—N1—C1 | −178.4 (3) |
C9—C4—C5—N1 | 175.1 (3) | C4—C5—N1—Pb | −160.2 (3) |
C3—C4—C5—C6 | 176.6 (4) | C6—C5—N1—Pb | 19.5 (4) |
C9—C4—C5—C6 | −4.5 (5) | C8—C7—N2—C6 | −1.5 (6) |
N1—C5—C6—N2 | 2.6 (5) | C8—C7—N2—Pb | −158.6 (3) |
C4—C5—C6—N2 | −177.7 (3) | C10—C6—N2—C7 | −0.9 (5) |
N1—C5—C6—C10 | −177.6 (3) | C5—C6—N2—C7 | 178.9 (3) |
C4—C5—C6—C10 | 2.0 (5) | C10—C6—N2—Pb | 157.9 (3) |
N2—C7—C8—C13 | 3.2 (7) | C5—C6—N2—Pb | −22.3 (4) |
C3—C4—C9—C11 | −178.6 (4) | N4—C12—N3—C9 | 0.6 (5) |
C5—C4—C9—C11 | 2.6 (6) | C11—C9—N3—C12 | −0.5 (4) |
C3—C4—C9—N3 | 4.8 (7) | C4—C9—N3—C12 | 176.5 (4) |
C5—C4—C9—N3 | −173.9 (4) | N3—C12—N4—C11 | −0.4 (5) |
N2—C6—C10—C13 | 1.6 (5) | C9—C11—N4—C12 | 0.1 (4) |
C5—C6—C10—C13 | −178.1 (3) | C10—C11—N4—C12 | −178.9 (4) |
N2—C6—C10—C11 | −177.7 (3) | C1—N1—Pb—N1i | 93.6 (3) |
C5—C6—C10—C11 | 2.5 (5) | C5—N1—Pb—N1i | −104.8 (3) |
N3—C9—C11—N4 | 0.2 (4) | C1—N1—Pb—N2i | 29.7 (3) |
C4—C9—C11—N4 | −177.1 (4) | C5—N1—Pb—N2i | −168.7 (3) |
N3—C9—C11—C10 | 179.3 (3) | C1—N1—Pb—N2 | 177.0 (3) |
C4—C9—C11—C10 | 2.0 (6) | C5—N1—Pb—N2 | −21.4 (2) |
C13—C10—C11—C9 | 176.2 (4) | C7—N2—Pb—N1 | 179.9 (3) |
C6—C10—C11—C9 | −4.5 (5) | C6—N2—Pb—N1 | 22.2 (2) |
C13—C10—C11—N4 | −4.9 (6) | C7—N2—Pb—N1i | −87.2 (3) |
C6—C10—C11—N4 | 174.4 (4) | C6—N2—Pb—N1i | 115.1 (3) |
C7—C8—C13—C10 | −2.3 (6) | C7—N2—Pb—N2i | −130.6 (3) |
C6—C10—C13—C8 | 0.0 (6) | C6—N2—Pb—N2i | 71.7 (2) |
Symmetry code: (i) −x+1, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3ii | 0.86 | 2.19 | 3.030 (6) | 165 |
N3—H3A···O2ii | 0.86 | 2.35 | 3.059 (6) | 140 |
Symmetry code: (ii) −x+1/2, −y−1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | [Pb(NO3)2(C13H8N4)2] |
Mr | 771.68 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 292 |
a, b, c (Å) | 19.203 (4), 7.3948 (15), 17.392 (4) |
β (°) | 100.48 (3) |
V (Å3) | 2428.5 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 7.02 |
Crystal size (mm) | 0.56 × 0.22 × 0.11 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.165, 0.453 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10060, 2402, 2170 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.064, 1.05 |
No. of reflections | 2402 |
No. of parameters | 195 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.89, −0.63 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3i | 0.86 | 2.19 | 3.030 (6) | 165 |
N3—H3A···O2i | 0.86 | 2.35 | 3.059 (6) | 140 |
Symmetry code: (i) −x+1/2, −y−1/2, −z. |
Acknowledgements
The authors thank the Natural Science Foundation of Jiangsu University and the Natural Science Foundation of Jilin Normal University for support.
References
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1,10-Phenanthroline and its derivatives are very important heteroaromatic N-donor chelating ligands for the construction of coordination compounds. (Che et al., 2008; Xu et al., 2008; Che et al., 2006). Whereas, only a handful of supramolecular architectures based on imidazo[4,5-f][1,10]phenanthroline ligand (L) have been described (Thomas et al., 2008). The present attempt at synthesizing a new lead complex with L ligand gave the title complex, [Pb(C13H8N4)2(NO3)2] (I), whose structure is reported here.
In the title compound I, each Pb atom is hexacoordinated by four N atoms (N1, N1i, N2, N2i) from two L ligand and two O (O1, O1i) atoms from two NO3- ions (Fig. 1). The Pb—N bond lengths are normal (Table 1), however, O1 and O1i could be described as being semicoordinated with long Pb—O lengths of 2.872 (5) Å. The PbN4O2 coordination polyhedron approximates a distorted octahedral configuration.
In the crystal structure, the mononuclear complex molecules are linked via intermolecular N—H···O and N—H··· N hydrogen bonds (Table 2) forming one-dimensional chains along [100] (Fig. 2). Withal, one-dimensional chains are stabilized by π-π interactions between the L rings planes of neighboring molecules with distances of 3.442 Å (Fig. 3), leading to a three-dimensional network.