Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113019045/fa3319sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113019045/fa3319Isup2.hkl |
CCDC reference: 962904
Chiral multifunctional materials are presently the object of research efforts in several areas (Xuan et al., 2012). An effective and simple strategy for introducing chirality into coordination compounds is the self-assembly of metal ions and ligands into asymmetrical frameworks (Che et al., 2009; Han & Hong, 2005). To this end, it is useful to employ bridging ligands with labile conformations, including chiral conformers, which together with metal centers may form homochiral crystals through spontaneous chiral resolution (Liu et al., 2007). 3-(Pyridin-4-yl)benzoic acid (L), which combines a pyridyl fragment with a benzoic acid group, is a typical unsymmetrical spacer, and has variable conformations resulting from free rotation about the bond joining the pyridyl and phenyl groups. If the two rings are neither coplanar nor mutually perpendicular in a given compound, L will have conformational chirality. So this ligand is a good candidate for use in attempts to obtain chiral metal–organic structures. So far, ligand L has been experimentally observed to form several helical coordination polymers where the left- and right-handed metal–organic helical chains are interwoven to form meso compounds (Wu et al., 2011; Luo et al., 2007). We report here the synthesis, structure and thermal stability of a lead(II) complex of L, viz. [Pb(L)2]n, (I). Interestingly, on crystallization there appears to have been spontaneous resolution into a racemic conglomerate of enantiopure crystals. Moreover, this homochiral crystal of (I) does not display a helical structure but is formed by a corrugated, chiral two-dimensional metal–organic network.
For the preparation of (I), a mixture of Pb(NO3)2 (0.033 g, 0.1 mmol), L (0.040 g, 0.2 mmol), NaOH (0.008 g, 0.2 mmol) and deionized water (10 ml) was sealed in a 25 ml Teflon-lined stainless steel autoclave. The autoclave was heated at 433 K for 3 d and then cooled slowly to room temperature. Colourless needle-like crystals of (I) suitable for X-ray analysis were obtained in 76% yield (based on Pb). IR spectra in the range of 400–4000 cm-1 were recorded from KBr pellets using a Bruker VECTOR22 spectrophotometer. Selected IR bands (cm-1): 3441 (w), 1691 (m), 1605 (s), 1554 (m), 1429 (w), 1383 (s), 1268 (m), 1067 (w), 765 (s), 676 (w).
Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were positioned geometrically and allowed to ride on their parent atoms. In all cases, Uiso(H) values were taken as 1.2 Ueq(C).
In (I), the six-coordinate PbII atom sits on a crystallographic twofold axis and has an irregular coordination sphere, which can be described as having a four-legged sawhorse geometry. The legs of the sawhorse are formed by bonds from Pb1 to the O atoms of two chelating carboxylate groups of two L ligands, while the crossbeam, distorted from linearity [N1—Pb—N1iii = 154.9 (4)°; see Table 2 for all symmetry codes], comprises bonds from Pb1 to the pyridine N atoms of another two symmetry-related L ligands (Fig. 1). The bond lengths about atom Pb1 range from 2.345 (8) to 2.733 (8) Å (Table 2), in agreement with those reported for PbII coordination polymers with aromatic carboxylic acids (Severance et al., 2012). The O1ii—Pb1—O2ii angle of 51.0 (3)° in the four-membered chelate is typical of such fragments, while the N—Pb1—O and the remaining O—Pb1—O angles fall in the wide range of 73.0 (2)–126.4 (2)°, reflecting the irregularity of the sawhorse geometry.
In (I), the deprotonated ligands L, which bridge pairs of PbII atoms, do not possess the achiral conformations with Cs symmetry that might be expected of the free ligand, but rather are twisted about the C6—C8 bond into chiral conformers with C1 symmetry [C5—C6—C8—C9 = 27.9 (12)°]. As the space group (C2) possesses only proper symmetry elements, the sense of this torsion angle is the same throughout the crystal, which is thus enantiomerically pure.
In all, each PbII center is coordinated by four different symmetry-related L fragments, while each ligand bridges two symmetry-related PbII centers. The overall structure is a homochiral two-dimensional metal–organic polymer with corrugated (4,4) nets (Fig. 2). This is different from the previously reported helical metal–organic structures incorporating ligands L. The separation of the adjacent metal ions bridged by a given ligand L is 11.6710 (5) Å. The two-dimensional net is distorted, as can be characterized by the diagonal Pb···Pb distances within a given four-membered (Pb) ring. With reference to Fig. 2, the diagonal distance Pb1···Pb1v of 13.5534 (6) Å is markedly shorter than the other diagonal distance Pb1i···Pb1ii, which is 19.0040 (8) Å. Interestingly, two equivalent nets are mutually interpenetrated, thus giving a twofold interpenetrating homochiral fabric (Fig. 3). These layers are stacked along the a axis (Fig. 4). The formation of chiral crystals (I) upon crystallization from what was presumably a racemate implies spontaneous chiral resolution. The refined absolute structure parameter (Flack, 1983) of 0.015 (18) indicates that the resolution was essentially complete. Although individual crystals are stereochemically pure, the bulk compound is expected to be a racemic conglomerate.
To examine the thermal stability of the solid, thermogravimetric analysis (TGA) of a crystalline sample was carried out under an air atmosphere from 303 to 900 K with a heating rate of 10 K min-1. As shown in Fig. 5, compound (I) is stable up to 613 K. Complete decomposition of (I) occurs in the temperature range 613–793 K. The remaining 37.62% may be PbO, in good agreement with the theoretical value of 36.98%. These TGA results indicate that the two-dimensional polymeric framework of (I) is stable up to 613 K.
For chiral metal-organic materials, see: Xuan, et al. (2012). For construction of homochiral conglomerates based on metal-organic helices, see: Che, et al. (2009); Han, et al. (2005); Liu, et al. (2007). For helical coordination polymers of 3-pyridin-4-ylbenzoicate ligand, see: Wu, et al. (2011); Luo, et al. (2007). For the bond distances, see: Severance, et al. (2012). For confirmation of spontaneous resolution, see: Flack, (1983).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
[Pb(C12H8NO2)2] | F(000) = 576 |
Mr = 603.58 | Dx = 2.013 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 2390 reflections |
a = 15.9945 (7) Å | θ = 3.0–26.0° |
b = 6.7767 (3) Å | µ = 8.51 mm−1 |
c = 9.5020 (4) Å | T = 296 K |
β = 104.795 (2)° | Block, colourless |
V = 995.77 (7) Å3 | 0.41 × 0.10 × 0.07 mm |
Z = 2 |
Siemens SMART CCD diffractometer | 1676 independent reflections |
Radiation source: fine-focus sealed tube | 1668 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ω scan | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→18 |
Tmin = 0.350, Tmax = 0.612 | k = −7→8 |
3618 measured reflections | l = −10→11 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0097P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
1676 reflections | Δρmax = 0.98 e Å−3 |
141 parameters | Δρmin = −1.93 e Å−3 |
1 restraint | Absolute structure: Flack (1983), ???? Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.015 (18) |
[Pb(C12H8NO2)2] | V = 995.77 (7) Å3 |
Mr = 603.58 | Z = 2 |
Monoclinic, C2 | Mo Kα radiation |
a = 15.9945 (7) Å | µ = 8.51 mm−1 |
b = 6.7767 (3) Å | T = 296 K |
c = 9.5020 (4) Å | 0.41 × 0.10 × 0.07 mm |
β = 104.795 (2)° |
Siemens SMART CCD diffractometer | 1676 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1668 reflections with I > 2σ(I) |
Tmin = 0.350, Tmax = 0.612 | Rint = 0.041 |
3618 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.075 | Δρmax = 0.98 e Å−3 |
S = 1.10 | Δρmin = −1.93 e Å−3 |
1676 reflections | Absolute structure: Flack (1983), ???? Friedel pairs |
141 parameters | Absolute structure parameter: 0.015 (18) |
1 restraint |
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 | 0.0000 | 0.2374 | 0.5000 | 0.03977 (15) | |
O1 | 0.0598 (5) | −0.5374 (12) | −0.3142 (10) | 0.071 (2) | |
O2 | 0.1223 (7) | −0.4909 (13) | −0.4902 (9) | 0.085 (3) | |
N1 | 0.0774 (5) | 0.1497 (12) | 0.2823 (9) | 0.0463 (19) | |
C1 | 0.1082 (6) | −0.4371 (15) | −0.3746 (12) | 0.049 (2) | |
C2 | 0.1433 (5) | −0.250 (4) | −0.3032 (8) | 0.041 (2) | |
C3 | 0.1938 (6) | −0.1221 (15) | −0.3646 (10) | 0.047 (2) | |
H3 | 0.2091 | −0.1593 | −0.4488 | 0.056* | |
C4 | 0.2204 (6) | 0.0561 (15) | −0.3016 (10) | 0.046 (2) | |
H4 | 0.2534 | 0.1392 | −0.3439 | 0.055* | |
C5 | 0.1986 (6) | 0.1155 (14) | −0.1742 (10) | 0.042 (2) | |
H5 | 0.2166 | 0.2377 | −0.1328 | 0.050* | |
C6 | 0.1495 (5) | −0.0107 (13) | −0.1094 (9) | 0.0349 (17) | |
C7 | 0.1232 (5) | −0.1901 (13) | −0.1747 (10) | 0.039 (2) | |
H7 | 0.0910 | −0.2743 | −0.1318 | 0.047* | |
C8 | 0.1249 (5) | 0.0463 (13) | 0.0260 (9) | 0.0355 (18) | |
C9 | 0.1149 (5) | 0.239 (4) | 0.0627 (8) | 0.0447 (16) | |
H9 | 0.1241 | 0.3401 | 0.0023 | 0.054* | |
C10 | 0.0909 (7) | 0.2842 (14) | 0.1897 (13) | 0.053 (4) | |
H10 | 0.0840 | 0.4163 | 0.2107 | 0.063* | |
C11 | 0.0876 (6) | −0.0373 (15) | 0.2471 (10) | 0.045 (2) | |
H11 | 0.0787 | −0.1351 | 0.3104 | 0.054* | |
C12 | 0.1108 (6) | −0.0959 (14) | 0.1225 (9) | 0.0406 (19) | |
H12 | 0.1168 | −0.2291 | 0.1037 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pb1 | 0.0582 (2) | 0.0347 (2) | 0.0326 (2) | 0.000 | 0.02288 (15) | 0.000 |
O1 | 0.086 (5) | 0.048 (5) | 0.086 (6) | −0.021 (4) | 0.035 (5) | −0.023 (4) |
O2 | 0.147 (8) | 0.066 (6) | 0.053 (5) | −0.028 (5) | 0.045 (5) | −0.035 (4) |
N1 | 0.058 (5) | 0.049 (5) | 0.037 (5) | 0.000 (3) | 0.022 (4) | −0.008 (3) |
C1 | 0.054 (5) | 0.038 (5) | 0.055 (6) | −0.004 (4) | 0.012 (5) | −0.011 (4) |
C2 | 0.045 (3) | 0.050 (6) | 0.031 (3) | 0.002 (8) | 0.018 (3) | −0.016 (7) |
C3 | 0.051 (5) | 0.060 (7) | 0.038 (5) | −0.006 (4) | 0.027 (4) | −0.005 (4) |
C4 | 0.052 (5) | 0.054 (6) | 0.041 (5) | −0.011 (4) | 0.029 (4) | −0.002 (4) |
C5 | 0.043 (4) | 0.049 (6) | 0.036 (5) | −0.007 (4) | 0.013 (4) | −0.005 (4) |
C6 | 0.034 (4) | 0.044 (5) | 0.030 (4) | 0.000 (3) | 0.016 (3) | −0.003 (3) |
C7 | 0.043 (4) | 0.045 (6) | 0.035 (5) | −0.002 (3) | 0.022 (4) | 0.003 (3) |
C8 | 0.033 (4) | 0.043 (5) | 0.032 (4) | −0.003 (3) | 0.011 (3) | −0.004 (3) |
C9 | 0.061 (4) | 0.041 (4) | 0.041 (4) | −0.004 (11) | 0.030 (3) | −0.006 (10) |
C10 | 0.069 (6) | 0.041 (11) | 0.055 (6) | −0.003 (4) | 0.029 (5) | −0.007 (4) |
C11 | 0.048 (5) | 0.056 (6) | 0.035 (5) | −0.002 (4) | 0.018 (4) | 0.004 (4) |
C12 | 0.050 (5) | 0.046 (5) | 0.031 (4) | 0.002 (4) | 0.020 (4) | −0.005 (3) |
Pb1—O1i | 2.345 (8) | C3—C4 | 1.367 (15) |
Pb1—O1ii | 2.345 (7) | C3—H3 | 0.9300 |
Pb1—O2ii | 2.670 (9) | C4—C5 | 1.401 (13) |
Pb1—O2i | 2.670 (9) | C4—H4 | 0.9300 |
Pb1—N1 | 2.733 (8) | C5—C6 | 1.406 (13) |
Pb1—N1iii | 2.733 (8) | C5—H5 | 0.9300 |
Pb1—C1i | 2.868 (9) | C6—C7 | 1.381 (13) |
Pb1—C1ii | 2.868 (9) | C6—C8 | 1.489 (11) |
O1—C1 | 1.271 (14) | C7—H7 | 0.9300 |
O1—Pb1iv | 2.345 (7) | C8—C9 | 1.37 (3) |
O2—C1 | 1.232 (13) | C8—C12 | 1.387 (13) |
O2—Pb1iv | 2.670 (9) | C9—C10 | 1.390 (14) |
N1—C10 | 1.322 (13) | C9—H9 | 0.9300 |
N1—C11 | 1.332 (13) | C10—H10 | 0.9300 |
C1—C2 | 1.48 (2) | C11—C12 | 1.386 (13) |
C1—Pb1iv | 2.868 (9) | C11—H11 | 0.9300 |
C2—C7 | 1.399 (12) | C12—H12 | 0.9300 |
C2—C3 | 1.41 (2) | ||
O1i—Pb1—O1ii | 98.8 (5) | O2—C1—Pb1iv | 68.3 (6) |
O1i—Pb1—O2ii | 74.4 (3) | O1—C1—Pb1iv | 53.4 (5) |
O1ii—Pb1—O2ii | 51.0 (3) | C2—C1—Pb1iv | 165.4 (7) |
O1i—Pb1—O2i | 51.0 (3) | C7—C2—C3 | 118.0 (16) |
O1ii—Pb1—O2i | 74.4 (3) | C7—C2—C1 | 120.1 (13) |
O2ii—Pb1—O2i | 92.8 (5) | C3—C2—C1 | 121.8 (8) |
O1i—Pb1—N1 | 122.3 (3) | C4—C3—C2 | 120.5 (10) |
O1ii—Pb1—N1 | 75.4 (3) | C4—C3—H3 | 119.7 |
O2ii—Pb1—N1 | 126.4 (2) | C2—C3—H3 | 119.7 |
O2i—Pb1—N1 | 73.0 (2) | C3—C4—C5 | 121.0 (8) |
O1i—Pb1—N1iii | 75.4 (3) | C3—C4—H4 | 119.5 |
O1ii—Pb1—N1iii | 122.3 (3) | C5—C4—H4 | 119.5 |
O2ii—Pb1—N1iii | 73.0 (2) | C4—C5—C6 | 119.6 (8) |
O2i—Pb1—N1iii | 126.4 (2) | C4—C5—H5 | 120.2 |
N1—Pb1—N1iii | 154.9 (4) | C6—C5—H5 | 120.2 |
O1i—Pb1—C1i | 25.8 (3) | C7—C6—C5 | 118.6 (8) |
O1ii—Pb1—C1i | 84.2 (3) | C7—C6—C8 | 120.0 (7) |
O2ii—Pb1—C1i | 81.0 (3) | C5—C6—C8 | 121.4 (8) |
O2i—Pb1—C1i | 25.4 (3) | C6—C7—C2 | 122.3 (11) |
N1—Pb1—C1i | 98.0 (3) | C6—C7—H7 | 118.8 |
N1iii—Pb1—C1i | 101.2 (3) | C2—C7—H7 | 118.8 |
O1i—Pb1—C1ii | 84.2 (3) | C9—C8—C12 | 116.3 (8) |
O1ii—Pb1—C1ii | 25.8 (3) | C9—C8—C6 | 122.7 (9) |
O2ii—Pb1—C1ii | 25.4 (3) | C12—C8—C6 | 121.0 (8) |
O2i—Pb1—C1ii | 81.0 (3) | C8—C9—C10 | 120.4 (17) |
N1—Pb1—C1ii | 101.2 (3) | C8—C9—H9 | 119.8 |
N1iii—Pb1—C1ii | 98.0 (3) | C10—C9—H9 | 119.8 |
C1i—Pb1—C1ii | 79.5 (4) | N1—C10—C9 | 123.7 (14) |
C1—O1—Pb1iv | 100.8 (7) | N1—C10—H10 | 118.2 |
C1—O2—Pb1iv | 86.3 (7) | C9—C10—H10 | 118.2 |
C10—N1—C11 | 115.9 (8) | N1—C11—C12 | 124.3 (9) |
C10—N1—Pb1 | 122.4 (6) | N1—C11—H11 | 117.8 |
C11—N1—Pb1 | 120.4 (6) | C12—C11—H11 | 117.8 |
O2—C1—O1 | 121.0 (9) | C11—C12—C8 | 119.3 (9) |
O2—C1—C2 | 121.9 (10) | C11—C12—H12 | 120.3 |
O1—C1—C2 | 117.1 (9) | C8—C12—H12 | 120.3 |
O1i—Pb1—N1—C10 | −61.6 (9) | C7—C2—C3—C4 | −1.4 (17) |
O1ii—Pb1—N1—C10 | 29.6 (8) | C1—C2—C3—C4 | 175.5 (11) |
O2ii—Pb1—N1—C10 | 32.4 (9) | C2—C3—C4—C5 | 0.4 (16) |
O2i—Pb1—N1—C10 | −48.2 (8) | C3—C4—C5—C6 | 0.7 (15) |
N1iii—Pb1—N1—C10 | 168.0 (8) | C4—C5—C6—C7 | −0.7 (13) |
C1i—Pb1—N1—C10 | −52.2 (8) | C4—C5—C6—C8 | 180.0 (8) |
C1ii—Pb1—N1—C10 | 28.6 (8) | C5—C6—C7—C2 | −0.4 (14) |
O1i—Pb1—N1—C11 | 131.8 (7) | C8—C6—C7—C2 | 179.0 (9) |
O1ii—Pb1—N1—C11 | −137.0 (7) | C3—C2—C7—C6 | 1.4 (16) |
O2ii—Pb1—N1—C11 | −134.1 (7) | C1—C2—C7—C6 | −175.6 (10) |
O2i—Pb1—N1—C11 | 145.2 (8) | C7—C6—C8—C9 | −151.5 (8) |
N1iii—Pb1—N1—C11 | 1.4 (7) | C5—C6—C8—C9 | 27.9 (12) |
C1i—Pb1—N1—C11 | 141.2 (7) | C7—C6—C8—C12 | 28.4 (12) |
C1ii—Pb1—N1—C11 | −138.0 (7) | C5—C6—C8—C12 | −152.2 (8) |
Pb1iv—O2—C1—O1 | 9.0 (11) | C12—C8—C9—C10 | −0.6 (12) |
Pb1iv—O2—C1—C2 | −168.2 (10) | C6—C8—C9—C10 | 179.3 (8) |
Pb1iv—O1—C1—O2 | −10.5 (12) | C11—N1—C10—C9 | −0.4 (15) |
Pb1iv—O1—C1—C2 | 166.9 (9) | Pb1—N1—C10—C9 | −167.5 (7) |
O2—C1—C2—C7 | 177.6 (12) | C8—C9—C10—N1 | 0.8 (15) |
O1—C1—C2—C7 | 0.3 (17) | C10—N1—C11—C12 | −0.1 (14) |
Pb1iv—C1—C2—C7 | 46 (4) | Pb1—N1—C11—C12 | 167.3 (7) |
O2—C1—C2—C3 | 0.8 (19) | N1—C11—C12—C8 | 0.2 (14) |
O1—C1—C2—C3 | −176.6 (11) | C9—C8—C12—C11 | 0.2 (12) |
Pb1iv—C1—C2—C3 | −130 (3) | C6—C8—C12—C11 | −179.7 (8) |
Symmetry codes: (i) x, y+1, z+1; (ii) −x, y+1, −z; (iii) −x, y, −z+1; (iv) x, y−1, z−1. |
Experimental details
Crystal data | |
Chemical formula | [Pb(C12H8NO2)2] |
Mr | 603.58 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 296 |
a, b, c (Å) | 15.9945 (7), 6.7767 (3), 9.5020 (4) |
β (°) | 104.795 (2) |
V (Å3) | 995.77 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 8.51 |
Crystal size (mm) | 0.41 × 0.10 × 0.07 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.350, 0.612 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3618, 1676, 1668 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.075, 1.10 |
No. of reflections | 1676 |
No. of parameters | 141 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.98, −1.93 |
Absolute structure | Flack (1983), ???? Friedel pairs |
Absolute structure parameter | 0.015 (18) |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1994), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Siemens, 1994).
Pb1—O1i | 2.345 (8) | Pb1—N1 | 2.733 (8) |
Pb1—O2i | 2.670 (9) | ||
O1i—Pb1—O1ii | 98.8 (5) | O1ii—Pb1—N1 | 75.4 (3) |
O1i—Pb1—O2ii | 74.4 (3) | O2ii—Pb1—N1 | 126.4 (2) |
O1ii—Pb1—O2ii | 51.0 (3) | O2i—Pb1—N1 | 73.0 (2) |
O2ii—Pb1—O2i | 92.8 (5) | N1—Pb1—N1iii | 154.9 (4) |
O1i—Pb1—N1 | 122.3 (3) |
Symmetry codes: (i) x, y+1, z+1; (ii) −x, y+1, −z; (iii) −x, y, −z+1. |
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