research communications
18H26N2)3[Pb4I14(DMSO)2]·2DMSO
of the lead-containing organic–inorganic hybrid: (CaState Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, Shandong Province, People's Republic of China, and bSchool of Chemistry and Environmental Engineering, Shandong University of Science and Technology, Qingdao, People's Republic of China
*Correspondence e-mail: lz@sdu.edu.cn
The title compound, tris(1,1′-dibutyl-4,4′-bipyridine-1,1′-diium) bis(dimethyl sulfoxide)di-μ3-iodido-tetra-μ2-iodido-octaiodidotetralead(II) dimethyl sulfoxide disolvate, (C18H26N2)3[Pb4I14(C2H6OS)2]·2C2H6OS, belongs to a class of organic–inorganic hybrid materials with novel functionalities. In this compound, C—H⋯O and C—H⋯I hydrogen-bonding interactions, π–π interactions, other short contacts and Pb octahedral chains are present, extending the into a three-dimensional supramolecular network.
Keywords: organic-inorganic hybrid; crystal structure; hydrogen-bonding interactions; π–π interactions.
CCDC reference: 1880239
1. Chemical context
Organic–inorganic hybrid materials have attracted more and more attention from researchers because of their interesting physical properties and novel functionalities, such as magnetism, ferroelectricity, electrical/optical properties and et al., 2017). The inorganic components provide rich structural possibilities, including discrete clusters, chains, layers and open frameworks, which dominate the significant electrical, optical and magnetic properties in hybrids (Sun et al., 2018). The organic moieties may exhibit unique molecular properties such as hyperpolarizability, photochromicity and polymerizability (Tang & Guloy, 1999). The title molecule was prepared by the reaction of (N,N′-disubstituted-4,4′-bipyridinium) and a metal halide. show excellent redox and chemical stability. In addition, they can act as effective templates for the construction of various organic–inorganic hybrids, charge-transfer complexes and supramolecular systems (Liu et al., 2017). As lead is a heavy p-block metal in the IVA group, lead(II) halide-based organic–inorganic hybrids possess a large radius, a flexible coordination environment, and variable stereochemical activities of the lead center (Li et al., 2012).
(Yao2. Structural commentary
The title compound crystallizes in the triclinic system in Pī. The consists of half a [(Pb4I14)]6− trianion, one and a half BV2+ (BV2+ = 1,1′-dibutyl-4,4′- bipyridinium) dications and two DMSO molecules, as shown in Fig. 1. The BV2+ cation is located on a general position and adopts a non-planar structure, with a dihedral angle of 27.5 (3)° between the planes of the pyridinium rings. In the bipyridinium rings, C—N bond lengths vary from 1.335 (9) to 1.499 (10) Å and C—C bond lengths from 1.336 (17) to 1.636 (17) Å. C—N—C bond angles are in the range 118.6 (6)–121.1 (7)° and C—C—C bond angles in the range 107.9 (9)–122.1 (6)°. The inorganic anion can be considered as a set of mixed face-shared/edge-shared octahedra (Krautscheid et al., 2001). Pb1—I bond lengths range from 3.0765 (5) to 3.4315 (5) Å and Pb2—I bond lengths from 3.0802 (5) to 3.4010 (5) Å. I—Pb1—I bond angles are in the range 82.007 (13)–172.112 (13)° and O—Pb2—I bond angles in the range 82.78 (10)-174.71 (9)°. All the above angles deviate from the angles of an ideal octahedron (90 and 180°) due to the stereochemical activity of the Pb (6s2) lone pairs (Li et al., 2005).
3. Supramolecular features
In the compound, the organic species interact with the inorganic [(Pb4I14)]6− and DMSO via C—H⋯I and C—H⋯O hydrogen bonds (Table 1). The C⋯I distances are in the range 3.668 (8)–3.940 (10) Å while the C⋯O distances are 3.093 (9) and 3.517 (10) Å. The C—H⋯I angle values vary from 136 to 168°. Hydrogen bonds between the anionic entities [(Pb4I14)]6− and organic species play an important role in stabilizing the (Fig. 2). In addition, there are weak π–π interactions between adjacent free BV2+ cations with centroid-to-centroid distances between the pyridyl groups ranging from 4.249 (4) to 4.796 (4) Å (Table 2).
4. Database survey
Lead(II) iodide complexes have been reported whose structures include chains of face-sharing ideal PbI6 octahedra (Krautscheid et al., 2001; She et al., 2014) and chains of corner-sharing PbI6 octahedra (Wang et al., 1995). The structure of 1,1′-dibutyl-4,4′-bipyridinium diiodide was reported by our research group (Zhao et al., 2012). Typical Pb–I-based hybrids templated with alkyl viologen cations include, for example, [(Pb6I22)(DMF)2(DPB)5] (Zhang et al., 2015), (C21H27N3)[Pb3I9] (Hong-Xu et al., 2010), (C14H18N2)[Pb2I6] (Pradeesh et al., 2010) and [IV][Pb2I6] (Kim et al., 2018).
5. Synthesis and crystallization
NaI (0.23 g, 1.5 mmol), PbI2 (0.46 g, 1.0 mmol) and 10 ml of methanol were stirred under an argon atmosphere until dissolved. 1,1′-Dibutyl-4,4′-bipyridyl cation salt (0.52 g, 1.0 mmol) dissolved in methanol (5 ml) was added to the reaction mixture at room temperature. The resulting precipitate was dissolved in DMSO (3 ml) and placed in a sealed jar of anhydrous ether. Red crystals were produced two weeks later under an argon-protected atmosphere. After filtering and drying under vacuum, red needle-shaped crystals of 0.73 g (72.3%) with high quality were obtained. Analysis calculated for C62H102I14N6O4Pb4S4: C 19.97, H 2.70, N 2.25%. Found: C 19.80, H 2.82, N 2.25%. IR (cm−1): 3291 (w), 3108 (m), 3035 (s), 2931 (w), 2958 (w), 2857 (w), 944 (w), 1636 (m), 1634 (s), 1441 (m), 1060 (s), 833 (s).
6. Refinement
Crystal data, data collection and structure . Hydrogen atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and were included in the in the riding-model approximation, with Uiso(H)= 1.2-1.5Ueq(C).
details are summarized in Table 3
|
Supporting information
CCDC reference: 1880239
https://doi.org/10.1107/S2056989018016584/ex2016sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018016584/ex2016Isup2.hkl
Data collection: APEX3 (Bruker, 2017); cell
SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).(C18H26N2)3[Pb4I14(C2H6OS)2]·2C2H6OS | Z = 2 |
Mr = 1864.54 | F(000) = 1682 |
Triclinic, P1 | Dx = 2.419 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.5011 (10) Å | Cell parameters from 29882 reflections |
b = 14.2262 (13) Å | θ = 1.8–25° |
c = 16.2969 (14) Å | µ = 10.90 mm−1 |
α = 80.305 (1)° | T = 296 K |
β = 78.449 (1)° | Needle, red |
γ = 81.753 (1)° | 0.55 × 0.50 × 0.09 mm |
V = 2558.5 (4) Å3 |
Bruker APEX3 CCD area-detector diffractometer | 8975 independent reflections |
Radiation source: fine-focus sealed tube | 8219 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | h = −13→13 |
Tmin = 0.065, Tmax = 0.440 | k = −16→16 |
24466 measured reflections | l = −19→19 |
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)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0562P)2 + 3.2208P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.059 |
8975 reflections | Δρmax = 2.47 e Å−3 |
432 parameters | Δρmin = −1.72 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Bruker, 2017), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00081 (6) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | −0.019011 (19) | 0.115698 (16) | 0.614407 (14) | 0.02456 (9) | |
Pb2 | 0.056844 (19) | 0.234124 (16) | 0.300143 (15) | 0.02475 (9) | |
I3 | −0.12457 (3) | 0.27930 (3) | 0.48471 (3) | 0.02923 (11) | |
I4 | −0.07737 (4) | 0.39067 (3) | 0.18256 (3) | 0.04282 (14) | |
I5 | 0.27864 (4) | 0.19949 (4) | 0.16274 (3) | 0.04566 (14) | |
I6 | 0.15180 (4) | 0.24586 (3) | 0.65461 (3) | 0.04339 (14) | |
I7 | −0.22112 (4) | 0.16826 (4) | 0.75974 (3) | 0.04122 (13) | |
C7 | 0.9915 (6) | 0.9485 (5) | 0.0111 (4) | 0.0338 (15) | |
N2 | 0.4596 (5) | 0.6917 (4) | 0.7240 (4) | 0.0363 (13) | |
C1 | 0.5880 (9) | 0.6807 (9) | 0.1101 (8) | 0.087 (3) | |
H1A | 0.5779 | 0.7078 | 0.0535 | 0.130* | |
H1B | 0.5298 | 0.7132 | 0.1499 | 0.130* | |
H1C | 0.5775 | 0.6137 | 0.1193 | 0.130* | |
C2 | 0.7139 (8) | 0.6923 (7) | 0.1220 (7) | 0.068 (3) | |
H2A | 0.7239 | 0.7601 | 0.1120 | 0.082* | |
H2B | 0.7218 | 0.6681 | 0.1801 | 0.082* | |
C3 | 0.8105 (7) | 0.6412 (5) | 0.0644 (5) | 0.050 (2) | |
H3A | 0.8006 | 0.6641 | 0.0064 | 0.060* | |
H3B | 0.8012 | 0.5733 | 0.0756 | 0.060* | |
C4 | 0.9363 (7) | 0.6536 (5) | 0.0728 (5) | 0.0496 (19) | |
H4A | 0.9479 | 0.6299 | 0.1303 | 0.059* | |
H4B | 0.9935 | 0.6161 | 0.0352 | 0.059* | |
N1 | 0.9583 (5) | 0.7570 (4) | 0.0515 (4) | 0.0368 (13) | |
C5 | 0.9825 (8) | 0.8037 (6) | 0.1095 (5) | 0.055 (2) | |
H5 | 0.9881 | 0.7715 | 0.1635 | 0.066* | |
C6 | 0.9992 (8) | 0.8996 (6) | 0.0897 (5) | 0.055 (2) | |
H6 | 1.0160 | 0.9314 | 0.1306 | 0.067* | |
C9 | 0.9507 (8) | 0.8038 (7) | −0.0262 (5) | 0.060 (2) | |
H9 | 0.9343 | 0.7710 | −0.0666 | 0.072* | |
C8 | 0.9665 (9) | 0.8976 (7) | −0.0468 (5) | 0.063 (3) | |
H8 | 0.9604 | 0.9284 | −0.1011 | 0.076* | |
C10 | 0.2978 (9) | 0.6823 (9) | 1.0341 (6) | 0.084 (3) | |
H10A | 0.2572 | 0.6397 | 1.0793 | 0.127* | |
H10B | 0.2407 | 0.7316 | 1.0127 | 0.127* | |
H10C | 0.3547 | 0.7110 | 1.0548 | 0.127* | |
C11 | 0.3623 (9) | 0.6262 (7) | 0.9635 (6) | 0.067 (3) | |
H11A | 0.3150 | 0.5765 | 0.9594 | 0.081* | |
H11B | 0.4382 | 0.5951 | 0.9771 | 0.081* | |
C12 | 0.3845 (7) | 0.6903 (6) | 0.8783 (5) | 0.0481 (19) | |
H12A | 0.3091 | 0.7237 | 0.8656 | 0.058* | |
H12B | 0.4353 | 0.7380 | 0.8812 | 0.058* | |
C13 | 0.4431 (7) | 0.6323 (5) | 0.8086 (5) | 0.0446 (18) | |
H13A | 0.5203 | 0.6018 | 0.8201 | 0.054* | |
H13B | 0.3944 | 0.5821 | 0.8083 | 0.054* | |
C14 | 0.3627 (6) | 0.7293 (5) | 0.6908 (5) | 0.0381 (16) | |
H14 | 0.2872 | 0.7185 | 0.7213 | 0.046* | |
C15 | 0.3738 (5) | 0.7837 (5) | 0.6123 (5) | 0.0393 (17) | |
H15 | 0.3059 | 0.8096 | 0.5899 | 0.047* | |
C16 | 0.4857 (5) | 0.8001 (5) | 0.5664 (5) | 0.0310 (15) | |
C19 | 0.4996 (5) | 0.8580 (5) | 0.4816 (5) | 0.0330 (16) | |
C23 | 0.5989 (6) | 0.9090 (5) | 0.4521 (5) | 0.0392 (16) | |
H23 | 0.6563 | 0.9058 | 0.4856 | 0.047* | |
C22 | 0.6111 (6) | 0.9628 (6) | 0.3748 (5) | 0.0468 (19) | |
H22 | 0.6775 | 0.9962 | 0.3555 | 0.056* | |
N3 | 0.5285 (5) | 0.9690 (4) | 0.3252 (4) | 0.0419 (15) | |
C24 | 0.5471 (8) | 1.0264 (7) | 0.2402 (6) | 0.064 (3) | |
H24A | 0.6019 | 1.0729 | 0.2383 | 0.077* | |
H24B | 0.4717 | 1.0613 | 0.2290 | 0.077* | |
C25 | 0.5966 (9) | 0.9636 (9) | 0.1732 (6) | 0.076 (3) | |
H25A | 0.5386 | 0.9216 | 0.1703 | 0.091* | |
H25B | 0.6685 | 0.9242 | 0.1864 | 0.091* | |
C26 | 0.6271 (12) | 1.0332 (11) | 0.0828 (8) | 0.112 (5) | |
H26A | 0.5573 | 1.0779 | 0.0735 | 0.134* | |
H26B | 0.6913 | 1.0699 | 0.0842 | 0.134* | |
C27 | 0.6594 (15) | 0.9805 (13) | 0.0197 (10) | 0.140 (6) | |
H27A | 0.7293 | 0.9371 | 0.0286 | 0.209* | |
H27B | 0.6767 | 1.0219 | −0.0331 | 0.209* | |
H27C | 0.5955 | 0.9445 | 0.0183 | 0.209* | |
C21 | 0.4319 (6) | 0.9209 (5) | 0.3527 (5) | 0.0430 (19) | |
H21 | 0.3755 | 0.9253 | 0.3181 | 0.052* | |
C20 | 0.4156 (5) | 0.8659 (5) | 0.4301 (5) | 0.0363 (16) | |
H20 | 0.3480 | 0.8338 | 0.4483 | 0.044* | |
C17 | 0.5853 (5) | 0.7597 (5) | 0.6030 (5) | 0.0378 (16) | |
H17 | 0.6619 | 0.7693 | 0.5740 | 0.045* | |
C18 | 0.5692 (6) | 0.7060 (5) | 0.6819 (5) | 0.0372 (16) | |
H18 | 0.6353 | 0.6794 | 0.7062 | 0.045* | |
S1 | 0.09717 (14) | 0.45421 (12) | 0.35969 (11) | 0.0341 (4) | |
O1 | 0.1616 (4) | 0.3631 (3) | 0.3269 (3) | 0.0348 (11) | |
C30 | 0.1581 (7) | 0.4585 (6) | 0.4499 (5) | 0.058 (2) | |
H30A | 0.1352 | 0.4060 | 0.4928 | 0.087* | |
H30B | 0.1285 | 0.5181 | 0.4710 | 0.087* | |
H30C | 0.2436 | 0.4537 | 0.4349 | 0.087* | |
C31 | 0.1638 (9) | 0.5487 (6) | 0.2894 (7) | 0.078 (3) | |
H31A | 0.2470 | 0.5437 | 0.2926 | 0.117* | |
H31B | 0.1248 | 0.6092 | 0.3047 | 0.117* | |
H31C | 0.1559 | 0.5445 | 0.2326 | 0.117* | |
S2 | 0.44397 (18) | 0.46100 (15) | 0.66133 (14) | 0.0493 (5) | |
O2 | 0.5347 (5) | 0.5287 (4) | 0.6236 (4) | 0.0671 (18) | |
C28 | 0.3245 (8) | 0.4909 (6) | 0.6066 (6) | 0.062 (2) | |
H28A | 0.2831 | 0.5519 | 0.6188 | 0.092* | |
H28B | 0.2707 | 0.4426 | 0.6240 | 0.092* | |
H28C | 0.3543 | 0.4945 | 0.5469 | 0.092* | |
C29 | 0.4998 (9) | 0.3496 (7) | 0.6250 (9) | 0.091 (4) | |
H29A | 0.4961 | 0.3549 | 0.5660 | 0.136* | |
H29B | 0.4523 | 0.3008 | 0.6566 | 0.136* | |
H29C | 0.5812 | 0.3327 | 0.6327 | 0.136* | |
I2 | 0.10647 (3) | −0.07348 (3) | 0.72885 (3) | 0.02993 (12) | |
I1 | −0.16306 (3) | −0.05420 (3) | 0.56721 (3) | 0.02845 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pb1 | 0.02601 (14) | 0.02141 (14) | 0.02844 (15) | −0.00252 (10) | −0.00949 (10) | −0.00442 (10) |
Pb2 | 0.02510 (14) | 0.02060 (14) | 0.03053 (15) | −0.00131 (10) | −0.00997 (10) | −0.00449 (10) |
I3 | 0.0275 (2) | 0.0228 (2) | 0.0371 (2) | −0.00003 (16) | −0.00946 (17) | −0.00164 (18) |
I4 | 0.0412 (3) | 0.0305 (3) | 0.0544 (3) | −0.0011 (2) | −0.0192 (2) | 0.0108 (2) |
I5 | 0.0392 (3) | 0.0600 (3) | 0.0366 (3) | 0.0084 (2) | −0.0076 (2) | −0.0147 (2) |
I6 | 0.0441 (3) | 0.0374 (3) | 0.0561 (3) | −0.0159 (2) | −0.0173 (2) | −0.0080 (2) |
I7 | 0.0369 (2) | 0.0492 (3) | 0.0397 (3) | −0.0072 (2) | −0.00319 (19) | −0.0148 (2) |
C7 | 0.029 (3) | 0.044 (4) | 0.032 (4) | −0.002 (3) | −0.010 (3) | −0.011 (3) |
N2 | 0.032 (3) | 0.036 (3) | 0.043 (3) | 0.002 (2) | −0.005 (2) | −0.021 (3) |
C1 | 0.061 (6) | 0.100 (9) | 0.100 (9) | −0.029 (6) | −0.022 (6) | 0.008 (7) |
C2 | 0.058 (5) | 0.063 (6) | 0.086 (7) | −0.017 (5) | −0.012 (5) | −0.009 (5) |
C3 | 0.072 (5) | 0.026 (4) | 0.056 (5) | −0.014 (4) | −0.031 (4) | 0.009 (3) |
C4 | 0.063 (5) | 0.037 (4) | 0.053 (5) | −0.004 (4) | −0.027 (4) | 0.001 (4) |
N1 | 0.043 (3) | 0.032 (3) | 0.040 (3) | −0.003 (3) | −0.016 (3) | −0.008 (3) |
C5 | 0.088 (6) | 0.041 (5) | 0.039 (4) | 0.013 (4) | −0.037 (4) | 0.000 (4) |
C6 | 0.093 (6) | 0.043 (5) | 0.045 (5) | 0.006 (4) | −0.046 (4) | −0.018 (4) |
C9 | 0.091 (7) | 0.071 (6) | 0.031 (4) | −0.046 (5) | −0.013 (4) | −0.008 (4) |
C8 | 0.106 (7) | 0.069 (6) | 0.028 (4) | −0.053 (6) | −0.019 (4) | 0.001 (4) |
C10 | 0.072 (7) | 0.132 (11) | 0.045 (5) | −0.002 (6) | −0.003 (5) | −0.018 (6) |
C11 | 0.074 (6) | 0.071 (7) | 0.055 (6) | −0.006 (5) | −0.013 (5) | −0.007 (5) |
C12 | 0.036 (4) | 0.059 (5) | 0.051 (5) | −0.002 (4) | −0.005 (3) | −0.020 (4) |
C13 | 0.049 (4) | 0.040 (4) | 0.047 (5) | 0.004 (3) | −0.012 (3) | −0.014 (4) |
C14 | 0.029 (3) | 0.040 (4) | 0.046 (4) | −0.003 (3) | −0.002 (3) | −0.015 (3) |
C15 | 0.018 (3) | 0.046 (4) | 0.058 (5) | 0.001 (3) | −0.007 (3) | −0.024 (4) |
C16 | 0.025 (3) | 0.029 (3) | 0.043 (4) | 0.000 (3) | −0.007 (3) | −0.019 (3) |
C19 | 0.020 (3) | 0.033 (4) | 0.050 (4) | 0.002 (3) | −0.004 (3) | −0.024 (3) |
C23 | 0.026 (3) | 0.047 (4) | 0.047 (4) | −0.010 (3) | −0.010 (3) | −0.007 (4) |
C22 | 0.027 (3) | 0.049 (5) | 0.067 (5) | −0.006 (3) | −0.008 (3) | −0.014 (4) |
N3 | 0.029 (3) | 0.044 (4) | 0.048 (4) | 0.008 (3) | −0.005 (3) | −0.008 (3) |
C24 | 0.040 (4) | 0.082 (7) | 0.063 (6) | 0.016 (4) | −0.015 (4) | −0.002 (5) |
C25 | 0.072 (6) | 0.108 (9) | 0.049 (6) | −0.012 (6) | −0.015 (5) | −0.011 (6) |
C26 | 0.108 (10) | 0.143 (12) | 0.092 (9) | 0.056 (9) | −0.055 (8) | −0.052 (9) |
C27 | 0.136 (13) | 0.164 (16) | 0.130 (14) | 0.020 (11) | −0.042 (11) | −0.062 (12) |
C21 | 0.020 (3) | 0.043 (4) | 0.072 (6) | 0.007 (3) | −0.017 (3) | −0.023 (4) |
C20 | 0.023 (3) | 0.040 (4) | 0.050 (4) | −0.001 (3) | −0.008 (3) | −0.017 (4) |
C17 | 0.021 (3) | 0.038 (4) | 0.058 (5) | 0.000 (3) | −0.011 (3) | −0.015 (4) |
C18 | 0.029 (3) | 0.033 (4) | 0.055 (5) | 0.004 (3) | −0.014 (3) | −0.020 (3) |
S1 | 0.0289 (8) | 0.0265 (8) | 0.0481 (10) | −0.0021 (6) | −0.0051 (7) | −0.0117 (7) |
O1 | 0.026 (2) | 0.031 (2) | 0.052 (3) | −0.0029 (18) | −0.007 (2) | −0.021 (2) |
C30 | 0.056 (5) | 0.064 (6) | 0.065 (6) | −0.002 (4) | −0.013 (4) | −0.040 (5) |
C31 | 0.065 (6) | 0.039 (5) | 0.123 (9) | −0.012 (4) | −0.009 (6) | 0.006 (5) |
S2 | 0.0485 (11) | 0.0429 (11) | 0.0629 (13) | −0.0001 (9) | −0.0184 (9) | −0.0197 (10) |
O2 | 0.049 (3) | 0.050 (4) | 0.113 (5) | −0.012 (3) | −0.015 (3) | −0.037 (4) |
C28 | 0.066 (5) | 0.037 (5) | 0.088 (7) | −0.012 (4) | −0.040 (5) | 0.009 (4) |
C29 | 0.060 (6) | 0.050 (6) | 0.168 (12) | 0.004 (5) | −0.011 (7) | −0.049 (7) |
I2 | 0.0277 (2) | 0.0258 (2) | 0.0380 (2) | −0.00431 (17) | −0.00994 (17) | −0.00347 (18) |
I1 | 0.0271 (2) | 0.0254 (2) | 0.0363 (2) | −0.00027 (16) | −0.01434 (17) | −0.00608 (18) |
Pb1—I7 | 3.0765 (5) | C14—H14 | 0.9300 |
Pb1—I6 | 3.1121 (5) | C15—C16 | 1.383 (9) |
Pb1—I3 | 3.1493 (5) | C15—H15 | 0.9300 |
Pb1—I2 | 3.3282 (5) | C16—C17 | 1.403 (9) |
Pb1—I1 | 3.3858 (5) | C16—C19 | 1.476 (10) |
Pb2—O1 | 2.473 (4) | C19—C20 | 1.384 (9) |
Pb2—I5 | 3.0802 (5) | C19—C23 | 1.400 (9) |
Pb2—I4 | 3.1266 (5) | C23—C22 | 1.351 (11) |
Pb2—I2i | 3.3053 (5) | C23—H23 | 0.9300 |
Pb2—I1i | 3.3187 (5) | C22—N3 | 1.350 (10) |
Pb2—I3 | 3.4010 (5) | C22—H22 | 0.9300 |
C7—C6 | 1.364 (10) | N3—C21 | 1.348 (9) |
C7—C8 | 1.378 (10) | N3—C24 | 1.479 (11) |
C7—C7ii | 1.481 (14) | C24—C25 | 1.499 (13) |
N2—C18 | 1.335 (9) | C24—H24A | 0.9700 |
N2—C14 | 1.340 (9) | C24—H24B | 0.9700 |
N2—C13 | 1.483 (10) | C25—C26 | 1.636 (17) |
C1—C2 | 1.534 (13) | C25—H25A | 0.9700 |
C1—H1A | 0.9600 | C25—H25B | 0.9700 |
C1—H1B | 0.9600 | C26—C27 | 1.336 (17) |
C1—H1C | 0.9600 | C26—H26A | 0.9700 |
C2—C3 | 1.491 (12) | C26—H26B | 0.9700 |
C2—H2A | 0.9700 | C27—H27A | 0.9600 |
C2—H2B | 0.9700 | C27—H27B | 0.9600 |
C3—C4 | 1.518 (11) | C27—H27C | 0.9600 |
C3—H3A | 0.9700 | C21—C20 | 1.361 (11) |
C3—H3B | 0.9700 | C21—H21 | 0.9300 |
C4—N1 | 1.499 (9) | C20—H20 | 0.9300 |
C4—H4A | 0.9700 | C17—C18 | 1.373 (10) |
C4—H4B | 0.9700 | C17—H17 | 0.9300 |
N1—C5 | 1.336 (9) | C18—H18 | 0.9300 |
N1—C9 | 1.341 (10) | S1—O1 | 1.522 (4) |
C5—C6 | 1.380 (11) | S1—C30 | 1.763 (8) |
C5—H5 | 0.9300 | S1—C31 | 1.770 (9) |
C6—H6 | 0.9300 | C30—H30A | 0.9600 |
C9—C8 | 1.349 (12) | C30—H30B | 0.9600 |
C9—H9 | 0.9300 | C30—H30C | 0.9600 |
C8—H8 | 0.9300 | C31—H31A | 0.9600 |
C10—C11 | 1.520 (13) | C31—H31B | 0.9600 |
C10—H10A | 0.9600 | C31—H31C | 0.9600 |
C10—H10B | 0.9600 | S2—O2 | 1.492 (6) |
C10—H10C | 0.9600 | S2—C28 | 1.749 (8) |
C11—C12 | 1.524 (12) | S2—C29 | 1.774 (9) |
C11—H11A | 0.9700 | C28—H28A | 0.9600 |
C11—H11B | 0.9700 | C28—H28B | 0.9600 |
C12—C13 | 1.508 (10) | C28—H28C | 0.9600 |
C12—H12A | 0.9700 | C29—H29A | 0.9600 |
C12—H12B | 0.9700 | C29—H29B | 0.9600 |
C13—H13A | 0.9700 | C29—H29C | 0.9600 |
C13—H13B | 0.9700 | I2—Pb2i | 3.3053 (5) |
C14—C15 | 1.371 (10) | I1—Pb2i | 3.3187 (5) |
I7—Pb1—I6 | 93.528 (15) | C12—C13—H13B | 109.1 |
I7—Pb1—I3 | 91.655 (15) | H13A—C13—H13B | 107.8 |
I6—Pb1—I3 | 93.038 (15) | N2—C14—C15 | 120.7 (6) |
I7—Pb1—I2 | 95.153 (14) | N2—C14—H14 | 119.7 |
I6—Pb1—I2 | 90.519 (14) | C15—C14—H14 | 119.7 |
I3—Pb1—I2 | 172.112 (13) | C14—C15—C16 | 120.2 (7) |
I7—Pb1—I1 | 93.512 (14) | C14—C15—H15 | 119.9 |
I6—Pb1—I1 | 170.159 (14) | C16—C15—H15 | 119.9 |
I3—Pb1—I1 | 93.622 (13) | C15—C16—C17 | 117.8 (7) |
I2—Pb1—I1 | 82.007 (13) | C15—C16—C19 | 121.0 (6) |
O1—Pb2—I5 | 84.47 (10) | C17—C16—C19 | 121.2 (6) |
O1—Pb2—I4 | 87.45 (11) | C20—C19—C23 | 118.0 (7) |
I5—Pb2—I4 | 94.693 (16) | C20—C19—C16 | 122.1 (6) |
O1—Pb2—I2i | 174.71 (9) | C23—C19—C16 | 119.9 (6) |
I5—Pb2—I2i | 100.234 (14) | C22—C23—C19 | 119.9 (7) |
I4—Pb2—I2i | 89.734 (15) | C22—C23—H23 | 120.0 |
O1—Pb2—I1i | 99.08 (11) | C19—C23—H23 | 120.0 |
I5—Pb2—I1i | 90.803 (14) | N3—C22—C23 | 121.1 (7) |
I4—Pb2—I1i | 171.859 (14) | N3—C22—H22 | 119.5 |
I2i—Pb2—I1i | 83.372 (13) | C23—C22—H22 | 119.5 |
O1—Pb2—I3 | 82.78 (10) | C21—N3—C22 | 119.9 (7) |
I5—Pb2—I3 | 162.883 (14) | C21—N3—C24 | 120.8 (7) |
I4—Pb2—I3 | 96.095 (14) | C22—N3—C24 | 119.3 (7) |
I2i—Pb2—I3 | 93.076 (12) | N3—C24—C25 | 111.0 (8) |
I1i—Pb2—I3 | 80.016 (12) | N3—C24—H24A | 109.4 |
Pb1—I3—Pb2 | 100.953 (13) | C25—C24—H24A | 109.4 |
C6—C7—C8 | 116.9 (7) | N3—C24—H24B | 109.4 |
C6—C7—C7ii | 121.8 (7) | C25—C24—H24B | 109.4 |
C8—C7—C7ii | 121.3 (8) | H24A—C24—H24B | 108.0 |
C18—N2—C14 | 121.1 (7) | C24—C25—C26 | 107.9 (9) |
C18—N2—C13 | 120.3 (6) | C24—C25—H25A | 110.1 |
C14—N2—C13 | 118.6 (6) | C26—C25—H25A | 110.1 |
C2—C1—H1A | 109.5 | C24—C25—H25B | 110.1 |
C2—C1—H1B | 109.5 | C26—C25—H25B | 110.1 |
H1A—C1—H1B | 109.5 | H25A—C25—H25B | 108.4 |
C2—C1—H1C | 109.5 | C27—C26—C25 | 110.1 (14) |
H1A—C1—H1C | 109.5 | C27—C26—H26A | 109.6 |
H1B—C1—H1C | 109.5 | C25—C26—H26A | 109.6 |
C3—C2—C1 | 113.3 (9) | C27—C26—H26B | 109.7 |
C3—C2—H2A | 108.9 | C25—C26—H26B | 109.6 |
C1—C2—H2A | 108.9 | H26A—C26—H26B | 108.1 |
C3—C2—H2B | 108.9 | C26—C27—H27A | 109.5 |
C1—C2—H2B | 108.9 | C26—C27—H27B | 109.5 |
H2A—C2—H2B | 107.7 | H27A—C27—H27B | 109.5 |
C2—C3—C4 | 114.6 (7) | C26—C27—H27C | 109.5 |
C2—C3—H3A | 108.6 | H27A—C27—H27C | 109.5 |
C4—C3—H3A | 108.6 | H27B—C27—H27C | 109.5 |
C2—C3—H3B | 108.6 | N3—C21—C20 | 121.1 (6) |
C4—C3—H3B | 108.6 | N3—C21—H21 | 119.4 |
H3A—C3—H3B | 107.6 | C20—C21—H21 | 119.4 |
N1—C4—C3 | 111.1 (6) | C21—C20—C19 | 119.9 (6) |
N1—C4—H4A | 109.4 | C21—C20—H20 | 120.1 |
C3—C4—H4A | 109.4 | C19—C20—H20 | 120.1 |
N1—C4—H4B | 109.4 | C18—C17—C16 | 119.7 (6) |
C3—C4—H4B | 109.4 | C18—C17—H17 | 120.1 |
H4A—C4—H4B | 108.0 | C16—C17—H17 | 120.1 |
C5—N1—C9 | 119.6 (7) | N2—C18—C17 | 120.6 (6) |
C5—N1—C4 | 120.8 (6) | N2—C18—H18 | 119.7 |
C9—N1—C4 | 119.6 (6) | C17—C18—H18 | 119.7 |
N1—C5—C6 | 120.2 (7) | O1—S1—C30 | 104.1 (3) |
N1—C5—H5 | 119.9 | O1—S1—C31 | 104.7 (4) |
C6—C5—H5 | 119.9 | C30—S1—C31 | 99.9 (5) |
C7—C6—C5 | 121.0 (7) | S1—O1—Pb2 | 123.4 (2) |
C7—C6—H6 | 119.5 | S1—C30—H30A | 109.5 |
C5—C6—H6 | 119.5 | S1—C30—H30B | 109.5 |
N1—C9—C8 | 121.2 (7) | H30A—C30—H30B | 109.5 |
N1—C9—H9 | 119.4 | S1—C30—H30C | 109.5 |
C8—C9—H9 | 119.4 | H30A—C30—H30C | 109.5 |
C9—C8—C7 | 121.1 (8) | H30B—C30—H30C | 109.5 |
C9—C8—H8 | 119.4 | S1—C31—H31A | 109.5 |
C7—C8—H8 | 119.5 | S1—C31—H31B | 109.5 |
C11—C10—H10A | 109.5 | H31A—C31—H31B | 109.5 |
C11—C10—H10B | 109.5 | S1—C31—H31C | 109.5 |
H10A—C10—H10B | 109.5 | H31A—C31—H31C | 109.5 |
C11—C10—H10C | 109.5 | H31B—C31—H31C | 109.5 |
H10A—C10—H10C | 109.5 | O2—S2—C28 | 108.1 (4) |
H10B—C10—H10C | 109.5 | O2—S2—C29 | 107.1 (4) |
C10—C11—C12 | 112.1 (8) | C28—S2—C29 | 98.0 (5) |
C10—C11—H11A | 109.2 | S2—C28—H28A | 109.5 |
C12—C11—H11A | 109.2 | S2—C28—H28B | 109.5 |
C10—C11—H11B | 109.2 | H28A—C28—H28B | 109.5 |
C12—C11—H11B | 109.2 | S2—C28—H28C | 109.5 |
H11A—C11—H11B | 107.9 | H28A—C28—H28C | 109.5 |
C13—C12—C11 | 111.1 (7) | H28B—C28—H28C | 109.5 |
C13—C12—H12A | 109.4 | S2—C29—H29A | 109.5 |
C11—C12—H12A | 109.4 | S2—C29—H29B | 109.5 |
C13—C12—H12B | 109.4 | H29A—C29—H29B | 109.5 |
C11—C12—H12B | 109.4 | S2—C29—H29C | 109.5 |
H12A—C12—H12B | 108.0 | H29A—C29—H29C | 109.5 |
N2—C13—C12 | 112.5 (6) | H29B—C29—H29C | 109.5 |
N2—C13—H13A | 109.1 | Pb2i—I2—Pb1 | 97.673 (13) |
C12—C13—H13A | 109.1 | Pb2i—I1—Pb1 | 96.290 (13) |
N2—C13—H13B | 109.1 | ||
I7—Pb1—I3—Pb2 | −173.613 (13) | C17—C16—C19—C23 | −28.4 (9) |
I6—Pb1—I3—Pb2 | 92.765 (15) | C20—C19—C23—C22 | −0.9 (10) |
I2—Pb1—I3—Pb2 | −23.93 (9) | C16—C19—C23—C22 | −179.3 (6) |
I1—Pb1—I3—Pb2 | −79.987 (13) | C19—C23—C22—N3 | 0.4 (11) |
O1—Pb2—I3—Pb1 | −98.01 (11) | C23—C22—N3—C21 | 0.0 (11) |
I5—Pb2—I3—Pb1 | −55.87 (5) | C23—C22—N3—C24 | −178.2 (7) |
I4—Pb2—I3—Pb1 | 175.355 (13) | C21—N3—C24—C25 | −79.3 (9) |
I2i—Pb2—I3—Pb1 | 85.294 (14) | C22—N3—C24—C25 | 98.9 (9) |
I1i—Pb2—I3—Pb1 | 2.580 (11) | N3—C24—C25—C26 | −174.4 (8) |
C1—C2—C3—C4 | 178.3 (8) | C24—C25—C26—C27 | −173.3 (11) |
C2—C3—C4—N1 | −61.5 (9) | C22—N3—C21—C20 | 0.2 (10) |
C3—C4—N1—C5 | 117.3 (8) | C24—N3—C21—C20 | 178.4 (7) |
C3—C4—N1—C9 | −61.1 (10) | N3—C21—C20—C19 | −0.7 (10) |
C9—N1—C5—C6 | 0.2 (12) | C23—C19—C20—C21 | 1.1 (9) |
C4—N1—C5—C6 | −178.2 (8) | C16—C19—C20—C21 | 179.4 (6) |
C8—C7—C6—C5 | −0.1 (13) | C15—C16—C17—C18 | 0.0 (9) |
C7ii—C7—C6—C5 | 179.7 (8) | C19—C16—C17—C18 | −179.8 (6) |
N1—C5—C6—C7 | 0.0 (14) | C14—N2—C18—C17 | −0.2 (9) |
C5—N1—C9—C8 | −0.4 (13) | C13—N2—C18—C17 | 179.1 (6) |
C4—N1—C9—C8 | 178.1 (8) | C16—C17—C18—N2 | 0.2 (10) |
N1—C9—C8—C7 | 0.3 (15) | C30—S1—O1—Pb2 | 126.1 (4) |
C6—C7—C8—C9 | −0.1 (14) | C31—S1—O1—Pb2 | −129.5 (5) |
C7ii—C7—C8—C9 | −179.8 (9) | I5—Pb2—O1—S1 | 150.1 (3) |
C10—C11—C12—C13 | −177.2 (8) | I4—Pb2—O1—S1 | 55.2 (3) |
C18—N2—C13—C12 | 112.7 (7) | I2i—Pb2—O1—S1 | −2.7 (15) |
C14—N2—C13—C12 | −68.0 (8) | I1i—Pb2—O1—S1 | −119.9 (3) |
C11—C12—C13—N2 | 176.7 (7) | I3—Pb2—O1—S1 | −41.3 (3) |
C18—N2—C14—C15 | 0.1 (10) | I7—Pb1—I2—Pb2i | 86.695 (15) |
C13—N2—C14—C15 | −179.2 (6) | I6—Pb1—I2—Pb2i | −179.716 (13) |
N2—C14—C15—C16 | 0.1 (10) | I3—Pb1—I2—Pb2i | −62.87 (9) |
C14—C15—C16—C17 | −0.2 (9) | I1—Pb1—I2—Pb2i | −6.140 (11) |
C14—C15—C16—C19 | 179.6 (6) | I7—Pb1—I1—Pb2i | −88.621 (15) |
C15—C16—C19—C20 | −26.5 (9) | I6—Pb1—I1—Pb2i | 46.99 (9) |
C17—C16—C19—C20 | 153.3 (6) | I3—Pb1—I1—Pb2i | 179.495 (10) |
C15—C16—C19—C23 | 151.8 (6) | I2—Pb1—I1—Pb2i | 6.097 (11) |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+2, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···I2iii | 0.93 | 2.94 | 3.668 (8) | 136 |
C18—H18···O1iv | 0.93 | 2.30 | 3.093 (9) | 142 |
C21—H21···I7v | 0.93 | 2.95 | 3.780 (7) | 150 |
C22—H22···I2iv | 0.93 | 2.86 | 3.776 (8) | 168 |
C23—H23···I1vi | 0.93 | 2.85 | 3.753 (7) | 165 |
C24—H24B···I5vii | 0.97 | 2.99 | 3.940 (10) | 166 |
C30—H30C···O2iv | 0.96 | 2.57 | 3.517 (10) | 169 |
Symmetry codes: (iii) x+1, y+1, z−1; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+1; (vi) x+1, y+1, z; (vii) x, y+1, z. |
Cg(I)···Cg(J): ring centroid I,J (numbered as in Fig. 1); Cg···Cg: distance between ring centroids; α: dihedral angle between planes I andJ; CgI_Perp: perpendicular distance of Cg(I) on ring J; CgJ_Perp: perpendicular distance of Cg(J) on ring I. |
Cg(I)···Cg(J) | Cg···Cg | α | CgI_Perp | CgJ_Perp |
Cg(2)···Cg(3)vi | 4.796 (4) | 27.5 (3) | 3.481 (3) | 3.970 (3) |
Cg(3)···Cg(2)vi | 4.795 (4) | 27.5 (3) | 3.970 (3) | 3.480 (3) |
Cg(3)···Cg(3)vi | 4.249 (4) | 0.0 (4) | 3.507 (3) | 3.507 (3) |
Symmetry code: (vi) 1 - x, 2 - y, 1 - z. |
Cg(I) | x | y | z |
Cg(1) | 0.9749 (3) | 0.8517 (2) | 0.03147 (19) |
Cg(2) | 0.4727 (2) | 0.7451 (2) | 0.6464 (2) |
Cg(3) | 0.5142 (2) | 0.9143 (2) | 0.4028 (2) |
Funding information
The research was supported by the Natural Science Foundation of Shandong Province (grant No. ZR2010EM017).
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