metal-organic compounds
catena-Poly[[[bis[4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol-κ2N7,N8]lead(II)]-μ-4,4′-oxydibenzoato-κ3O,O′:O′′] dihydrate]
aXi'an Modern Chemistry Research Institute, Xi'an 710065, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The carboxylate dianion in the title compound, [Pb(C14H8O5)(C19H12N4O)2]·2H2O, uses one carboxylate group to O,O′-chelate a bis[4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol]-chelated PbII atom and uses its other carboxylate group to bind to another PbII atom in an irregular monodentate manner. The PbII atom exists in an undefined seven-coordinate geometry in the chain structure; the lone pair is stereochemically active. Adjacent chains are linked by intermolecular O—H⋯N, N—H⋯O and O—H⋯O hydrogen bonds that involve the uncoordinated water molecules to form a three-dimensional network.
Related literature
For a transition metal dicarboxylate adduct of 4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol, see: Xu et al. (2008).
Experimental
Crystal data
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Refinement
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Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
Supporting information
10.1107/S1600536808010805/si2072sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010805/si2072Isup2.hkl
Lead(II) nitrate (0.1 mmol), 1,4-oxobis(benzoic acid), 4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol (0.1 mmol) and water (14 ml) were heated in a 23 ml, Teflon-lined, stainless-steel Parr bomb at 458 K for 3 days. Crystals were obtained in 30% yield.
The carbon- and nitrogen-bound H atoms were placed in calculated positions [C—H 0.93, N—H 0.86, O—H 0.82 Å and Uiso(H)= 1.2Ueq(C, N, O)], and were included in the
in the riding-model approximation.Data collection: RAPID-AUTO (Rigaku, 1998); cell
RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).Fig. 1. Thermal ellipsoid plot of a portion of the chain structure of Pb(C19H12N4O)2(C14H8O5).2H2O; displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. Symmetry codes are given in Table 1. | |
Fig. 2. Seven-coordinate environment of lead. |
[Pb(C14H8O5)(C19H12N4O)2]·2H2O | F(000) = 2232 |
Mr = 1124.08 | Dx = 1.709 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 24960 reflections |
a = 10.767 (4) Å | θ = 3.0–27.5° |
b = 29.916 (7) Å | µ = 3.93 mm−1 |
c = 13.688 (4) Å | T = 295 K |
β = 97.70 (1)° | Block, colorless |
V = 4369 (2) Å3 | 0.33 × 0.24 × 0.21 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 9977 independent reflections |
Radiation source: fine-focus sealed tube | 6235 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −38→38 |
Tmin = 0.188, Tmax = 0.492 | l = −17→17 |
42355 measured reflections |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0814P)2 + 9.1333P] where P = (Fo2 + 2Fc2)/3 |
9977 reflections | (Δ/σ)max = 0.001 |
631 parameters | Δρmax = 1.52 e Å−3 |
0 restraints | Δρmin = −1.10 e Å−3 |
[Pb(C14H8O5)(C19H12N4O)2]·2H2O | V = 4369 (2) Å3 |
Mr = 1124.08 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.767 (4) Å | µ = 3.93 mm−1 |
b = 29.916 (7) Å | T = 295 K |
c = 13.688 (4) Å | 0.33 × 0.24 × 0.21 mm |
β = 97.70 (1)° |
Rigaku R-AXIS RAPID diffractometer | 9977 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 6235 reflections with I > 2σ(I) |
Tmin = 0.188, Tmax = 0.492 | Rint = 0.063 |
42355 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.02 | Δρmax = 1.52 e Å−3 |
9977 reflections | Δρmin = −1.10 e Å−3 |
631 parameters |
x | y | z | Uiso*/Ueq | ||
Pb1 | 0.22221 (3) | 0.252248 (8) | 0.632884 (19) | 0.04982 (12) | |
O1 | 0.1768 (7) | 0.31678 (17) | 0.5080 (4) | 0.0838 (19) | |
O2 | 0.1246 (6) | 0.33913 (18) | 0.6496 (4) | 0.0704 (15) | |
O3 | 0.2197 (8) | 0.5257 (2) | 0.4374 (5) | 0.099 (2) | |
O4 | 0.4930 (7) | 0.6379 (2) | 0.7966 (5) | 0.094 (2) | |
O5 | 0.3496 (9) | 0.6846 (2) | 0.7428 (5) | 0.114 (3) | |
O6 | 1.0871 (7) | 0.0039 (2) | 0.2469 (5) | 0.092 (2) | |
H6O | 1.0994 | 0.0068 | 0.1894 | 0.138* | |
O7 | 0.9813 (8) | 0.5095 (3) | 1.2543 (5) | 0.124 (3) | |
H7O | 1.0442 | 0.5223 | 1.2408 | 0.186* | |
O1W | 0.8513 (7) | 0.0694 (2) | 0.6615 (5) | 0.097 (2) | |
H1W1 | 0.8047 | 0.0778 | 0.6127 | 0.145* | |
H1W2 | 0.8102 | 0.0643 | 0.7066 | 0.145* | |
O2W | 0.8223 (7) | 0.4435 (3) | 0.7773 (5) | 0.128 (3) | |
H2W1 | 0.7757 | 0.4259 | 0.8005 | 0.191* | |
H2W2 | 0.7958 | 0.4477 | 0.7191 | 0.191* | |
N1 | 0.3196 (6) | 0.2288 (2) | 0.4707 (4) | 0.0541 (15) | |
N2 | 0.4077 (6) | 0.19747 (19) | 0.6534 (4) | 0.0560 (15) | |
N3 | 0.6337 (6) | 0.13120 (19) | 0.3461 (4) | 0.0542 (15) | |
H3N | 0.6276 | 0.1356 | 0.2836 | 0.065* | |
N4 | 0.7003 (6) | 0.10439 (19) | 0.4949 (4) | 0.0554 (15) | |
N5 | 0.3031 (6) | 0.27173 (18) | 0.8164 (4) | 0.0491 (14) | |
N6 | 0.4143 (6) | 0.30027 (19) | 0.6616 (4) | 0.0512 (14) | |
N7 | 0.6079 (6) | 0.36530 (19) | 1.0242 (4) | 0.0516 (14) | |
H7N | 0.5899 | 0.3632 | 1.0834 | 0.062* | |
N8 | 0.7061 (6) | 0.38671 (19) | 0.8986 (4) | 0.0536 (15) | |
C1 | 0.1535 (8) | 0.3474 (3) | 0.5655 (6) | 0.065 (2) | |
C2 | 0.1686 (8) | 0.3954 (3) | 0.5314 (6) | 0.061 (2) | |
C3 | 0.1180 (8) | 0.4303 (2) | 0.5783 (6) | 0.066 (2) | |
H3 | 0.0716 | 0.4248 | 0.6297 | 0.079* | |
C4 | 0.1373 (9) | 0.4749 (3) | 0.5474 (6) | 0.069 (2) | |
H4 | 0.1044 | 0.4988 | 0.5788 | 0.082* | |
C5 | 0.2045 (9) | 0.4823 (3) | 0.4712 (7) | 0.072 (2) | |
C6 | 0.2548 (10) | 0.4470 (3) | 0.4242 (7) | 0.084 (3) | |
H6 | 0.2991 | 0.4528 | 0.3717 | 0.101* | |
C7 | 0.2405 (9) | 0.4042 (3) | 0.4532 (6) | 0.075 (3) | |
H7 | 0.2772 | 0.3808 | 0.4225 | 0.090* | |
C8 | 0.2650 (11) | 0.5560 (3) | 0.5087 (6) | 0.079 (3) | |
C9 | 0.3789 (11) | 0.5484 (3) | 0.5651 (7) | 0.098 (3) | |
H9 | 0.4252 | 0.5230 | 0.5548 | 0.117* | |
C10 | 0.4246 (11) | 0.5793 (3) | 0.6381 (7) | 0.096 (3) | |
H10 | 0.5000 | 0.5737 | 0.6779 | 0.115* | |
C11 | 0.3572 (9) | 0.6186 (3) | 0.6515 (6) | 0.070 (2) | |
C12 | 0.2442 (9) | 0.6260 (4) | 0.5880 (7) | 0.084 (3) | |
H12 | 0.1993 | 0.6523 | 0.5934 | 0.101* | |
C13 | 0.2011 (9) | 0.5948 (3) | 0.5191 (7) | 0.077 (2) | |
H13 | 0.1264 | 0.6001 | 0.4781 | 0.093* | |
C14 | 0.4078 (11) | 0.6516 (3) | 0.7334 (7) | 0.090 (3) | |
C15 | 0.2765 (9) | 0.2453 (2) | 0.3820 (6) | 0.065 (2) | |
H15 | 0.2113 | 0.2659 | 0.3768 | 0.078* | |
C16 | 0.3252 (10) | 0.2329 (3) | 0.2974 (5) | 0.072 (2) | |
H16 | 0.2946 | 0.2457 | 0.2371 | 0.086* | |
C17 | 0.4159 (8) | 0.2026 (3) | 0.3029 (5) | 0.061 (2) | |
H17 | 0.4484 | 0.1937 | 0.2463 | 0.073* | |
C18 | 0.4623 (7) | 0.1841 (2) | 0.3943 (5) | 0.0534 (18) | |
C19 | 0.4116 (7) | 0.1985 (2) | 0.4769 (5) | 0.0478 (16) | |
C20 | 0.5610 (7) | 0.1511 (2) | 0.4104 (5) | 0.0522 (17) | |
C21 | 0.7153 (8) | 0.1039 (2) | 0.3996 (6) | 0.0575 (19) | |
C22 | 0.8102 (8) | 0.0774 (3) | 0.3582 (6) | 0.060 (2) | |
C23 | 0.8326 (9) | 0.0832 (2) | 0.2636 (6) | 0.066 (2) | |
H23 | 0.7873 | 0.1044 | 0.2240 | 0.079* | |
C24 | 0.9235 (9) | 0.0574 (3) | 0.2253 (6) | 0.069 (2) | |
H24 | 0.9353 | 0.0603 | 0.1596 | 0.083* | |
C25 | 0.9933 (9) | 0.0285 (3) | 0.2840 (7) | 0.076 (2) | |
C26 | 0.9773 (12) | 0.0230 (4) | 0.3790 (7) | 0.116 (5) | |
H26 | 1.0265 | 0.0030 | 0.4194 | 0.139* | |
C27 | 0.8852 (12) | 0.0481 (4) | 0.4143 (8) | 0.110 (4) | |
H27 | 0.8739 | 0.0447 | 0.4801 | 0.132* | |
C28 | 0.6054 (7) | 0.1341 (2) | 0.5018 (5) | 0.0519 (17) | |
C29 | 0.5571 (8) | 0.1494 (2) | 0.5886 (5) | 0.0532 (18) | |
C30 | 0.4597 (7) | 0.1814 (2) | 0.5749 (5) | 0.0475 (16) | |
C31 | 0.5963 (9) | 0.1339 (3) | 0.6837 (6) | 0.075 (3) | |
H31 | 0.6577 | 0.1119 | 0.6944 | 0.090* | |
C32 | 0.5450 (10) | 0.1509 (3) | 0.7599 (6) | 0.088 (3) | |
H32 | 0.5733 | 0.1418 | 0.8240 | 0.106* | |
C33 | 0.4502 (9) | 0.1819 (3) | 0.7424 (6) | 0.072 (2) | |
H33 | 0.4139 | 0.1925 | 0.7958 | 0.087* | |
C34 | 0.2457 (8) | 0.2584 (2) | 0.8911 (6) | 0.0573 (19) | |
H34 | 0.1771 | 0.2394 | 0.8778 | 0.069* | |
C35 | 0.2824 (8) | 0.2712 (3) | 0.9875 (6) | 0.062 (2) | |
H35 | 0.2385 | 0.2610 | 1.0372 | 0.074* | |
C36 | 0.3824 (7) | 0.2986 (2) | 1.0100 (5) | 0.0542 (18) | |
H36 | 0.4086 | 0.3072 | 1.0749 | 0.065* | |
C37 | 0.4461 (6) | 0.3140 (2) | 0.9323 (5) | 0.0439 (15) | |
C38 | 0.4027 (7) | 0.2994 (2) | 0.8353 (5) | 0.0445 (15) | |
C39 | 0.5495 (7) | 0.3434 (2) | 0.9428 (5) | 0.0487 (16) | |
C40 | 0.6998 (7) | 0.3911 (2) | 0.9936 (5) | 0.0534 (18) | |
C41 | 0.7755 (7) | 0.4217 (3) | 1.0608 (6) | 0.0593 (19) | |
C42 | 0.7432 (11) | 0.4316 (4) | 1.1507 (8) | 0.116 (5) | |
H42 | 0.6739 | 0.4175 | 1.1707 | 0.140* | |
C43 | 0.8099 (13) | 0.4621 (5) | 1.2140 (9) | 0.133 (6) | |
H43 | 0.7826 | 0.4698 | 1.2733 | 0.160* | |
C44 | 0.9163 (9) | 0.4804 (3) | 1.1872 (7) | 0.083 (3) | |
C45 | 0.9535 (8) | 0.4709 (3) | 1.1008 (6) | 0.073 (2) | |
H45 | 1.0265 | 0.4834 | 1.0834 | 0.087* | |
C46 | 0.8813 (8) | 0.4416 (3) | 1.0360 (6) | 0.072 (2) | |
H46 | 0.9059 | 0.4356 | 0.9748 | 0.086* | |
C47 | 0.6115 (6) | 0.3568 (2) | 0.8667 (5) | 0.0493 (16) | |
C48 | 0.5710 (7) | 0.3414 (2) | 0.7678 (5) | 0.0496 (16) | |
C49 | 0.4643 (7) | 0.3140 (2) | 0.7525 (5) | 0.0477 (16) | |
C50 | 0.6268 (8) | 0.3542 (3) | 0.6863 (6) | 0.066 (2) | |
H50 | 0.6980 | 0.3722 | 0.6944 | 0.079* | |
C51 | 0.5767 (9) | 0.3404 (3) | 0.5946 (6) | 0.074 (2) | |
H51 | 0.6132 | 0.3486 | 0.5394 | 0.089* | |
C52 | 0.4692 (9) | 0.3134 (3) | 0.5850 (6) | 0.068 (2) | |
H52 | 0.4349 | 0.3043 | 0.5222 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pb1 | 0.06011 (19) | 0.04550 (16) | 0.04314 (16) | −0.00172 (12) | 0.00430 (12) | −0.00412 (12) |
O1 | 0.151 (6) | 0.047 (3) | 0.056 (3) | 0.019 (3) | 0.023 (4) | 0.001 (3) |
O2 | 0.094 (4) | 0.069 (3) | 0.053 (3) | 0.002 (3) | 0.026 (3) | 0.002 (3) |
O3 | 0.154 (7) | 0.065 (4) | 0.074 (4) | −0.025 (4) | 0.000 (4) | 0.002 (3) |
O4 | 0.112 (6) | 0.090 (5) | 0.074 (4) | −0.002 (4) | −0.007 (4) | −0.011 (4) |
O5 | 0.199 (9) | 0.065 (4) | 0.080 (5) | 0.022 (5) | 0.032 (5) | −0.011 (4) |
O6 | 0.108 (5) | 0.098 (5) | 0.077 (4) | 0.016 (4) | 0.039 (4) | −0.020 (4) |
O7 | 0.129 (7) | 0.160 (7) | 0.088 (5) | −0.084 (6) | 0.031 (5) | −0.058 (5) |
O1W | 0.109 (5) | 0.111 (5) | 0.067 (4) | 0.035 (4) | 0.003 (4) | −0.012 (4) |
O2W | 0.120 (6) | 0.166 (8) | 0.087 (5) | −0.080 (6) | −0.021 (4) | 0.042 (5) |
N1 | 0.075 (4) | 0.050 (3) | 0.036 (3) | −0.001 (3) | 0.003 (3) | −0.004 (3) |
N2 | 0.077 (4) | 0.051 (3) | 0.042 (3) | 0.009 (3) | 0.013 (3) | −0.001 (3) |
N3 | 0.079 (4) | 0.052 (3) | 0.034 (3) | 0.000 (3) | 0.015 (3) | −0.004 (3) |
N4 | 0.071 (4) | 0.050 (3) | 0.046 (3) | 0.007 (3) | 0.013 (3) | −0.007 (3) |
N5 | 0.062 (4) | 0.042 (3) | 0.044 (3) | −0.008 (3) | 0.012 (3) | −0.007 (3) |
N6 | 0.065 (4) | 0.052 (3) | 0.036 (3) | −0.005 (3) | 0.005 (3) | −0.007 (3) |
N7 | 0.061 (4) | 0.051 (3) | 0.042 (3) | −0.005 (3) | 0.004 (3) | −0.006 (3) |
N8 | 0.056 (4) | 0.052 (3) | 0.053 (4) | −0.005 (3) | 0.006 (3) | −0.002 (3) |
C1 | 0.086 (6) | 0.054 (4) | 0.056 (5) | 0.011 (4) | 0.012 (4) | 0.000 (4) |
C2 | 0.067 (5) | 0.058 (4) | 0.054 (5) | −0.002 (4) | 0.000 (4) | 0.004 (4) |
C3 | 0.084 (6) | 0.053 (4) | 0.060 (5) | 0.008 (4) | 0.004 (4) | −0.004 (4) |
C4 | 0.088 (6) | 0.057 (4) | 0.060 (5) | 0.005 (4) | 0.005 (5) | −0.006 (4) |
C5 | 0.088 (6) | 0.055 (4) | 0.072 (6) | −0.009 (4) | 0.011 (5) | −0.001 (4) |
C6 | 0.115 (8) | 0.064 (5) | 0.078 (6) | −0.008 (5) | 0.027 (6) | 0.006 (5) |
C7 | 0.099 (7) | 0.067 (5) | 0.062 (5) | −0.014 (5) | 0.027 (5) | −0.001 (4) |
C8 | 0.124 (9) | 0.062 (5) | 0.049 (5) | −0.018 (5) | 0.006 (5) | 0.003 (4) |
C9 | 0.135 (10) | 0.073 (6) | 0.076 (6) | 0.026 (6) | −0.018 (6) | 0.001 (5) |
C10 | 0.128 (9) | 0.074 (6) | 0.077 (6) | 0.021 (6) | −0.015 (6) | −0.018 (5) |
C11 | 0.090 (7) | 0.060 (5) | 0.063 (5) | 0.001 (4) | 0.022 (5) | 0.004 (4) |
C12 | 0.081 (7) | 0.091 (7) | 0.079 (6) | 0.008 (5) | 0.007 (5) | 0.002 (6) |
C13 | 0.076 (6) | 0.080 (6) | 0.074 (6) | −0.007 (5) | 0.003 (5) | −0.002 (5) |
C14 | 0.133 (9) | 0.078 (6) | 0.050 (5) | 0.044 (6) | −0.021 (5) | −0.011 (5) |
C15 | 0.083 (6) | 0.062 (5) | 0.047 (4) | 0.009 (4) | −0.001 (4) | 0.000 (4) |
C16 | 0.109 (7) | 0.069 (5) | 0.032 (4) | 0.008 (5) | −0.004 (4) | −0.003 (4) |
C17 | 0.080 (6) | 0.066 (5) | 0.036 (4) | 0.000 (4) | 0.009 (4) | 0.003 (3) |
C18 | 0.073 (5) | 0.051 (4) | 0.039 (4) | −0.010 (3) | 0.015 (4) | −0.006 (3) |
C19 | 0.064 (5) | 0.041 (3) | 0.036 (3) | −0.004 (3) | 0.001 (3) | −0.001 (3) |
C20 | 0.073 (5) | 0.046 (3) | 0.039 (4) | −0.002 (3) | 0.011 (3) | 0.001 (3) |
C21 | 0.076 (5) | 0.051 (4) | 0.048 (4) | 0.004 (4) | 0.014 (4) | −0.011 (3) |
C22 | 0.077 (6) | 0.056 (4) | 0.049 (4) | 0.000 (4) | 0.017 (4) | −0.010 (4) |
C23 | 0.091 (6) | 0.051 (4) | 0.058 (5) | −0.002 (4) | 0.018 (4) | −0.012 (4) |
C24 | 0.087 (6) | 0.069 (5) | 0.056 (5) | 0.002 (5) | 0.029 (5) | −0.012 (4) |
C25 | 0.094 (7) | 0.065 (5) | 0.074 (6) | 0.010 (5) | 0.030 (5) | −0.015 (5) |
C26 | 0.158 (12) | 0.124 (9) | 0.073 (7) | 0.084 (8) | 0.043 (7) | 0.016 (6) |
C27 | 0.160 (12) | 0.112 (8) | 0.066 (6) | 0.057 (8) | 0.042 (7) | 0.001 (6) |
C28 | 0.067 (5) | 0.049 (4) | 0.041 (4) | 0.001 (3) | 0.014 (3) | −0.005 (3) |
C29 | 0.075 (5) | 0.048 (4) | 0.038 (4) | 0.006 (3) | 0.010 (3) | 0.001 (3) |
C30 | 0.065 (5) | 0.045 (3) | 0.033 (3) | −0.005 (3) | 0.008 (3) | −0.003 (3) |
C31 | 0.098 (7) | 0.081 (6) | 0.048 (5) | 0.035 (5) | 0.020 (4) | 0.010 (4) |
C32 | 0.117 (8) | 0.102 (7) | 0.045 (5) | 0.047 (6) | 0.013 (5) | 0.018 (5) |
C33 | 0.099 (7) | 0.076 (5) | 0.043 (4) | 0.033 (5) | 0.013 (4) | 0.004 (4) |
C34 | 0.062 (5) | 0.053 (4) | 0.058 (5) | −0.012 (3) | 0.011 (4) | −0.011 (4) |
C35 | 0.083 (6) | 0.059 (4) | 0.046 (4) | −0.005 (4) | 0.020 (4) | 0.002 (4) |
C36 | 0.068 (5) | 0.058 (4) | 0.036 (4) | −0.002 (4) | 0.004 (3) | −0.003 (3) |
C37 | 0.049 (4) | 0.044 (3) | 0.038 (3) | 0.004 (3) | 0.003 (3) | 0.003 (3) |
C38 | 0.057 (4) | 0.038 (3) | 0.038 (3) | 0.002 (3) | 0.006 (3) | −0.004 (3) |
C39 | 0.060 (4) | 0.046 (3) | 0.040 (4) | −0.003 (3) | 0.005 (3) | −0.004 (3) |
C40 | 0.059 (5) | 0.051 (4) | 0.048 (4) | −0.005 (3) | 0.000 (3) | −0.004 (3) |
C41 | 0.060 (5) | 0.069 (5) | 0.048 (4) | −0.011 (4) | 0.002 (4) | −0.012 (4) |
C42 | 0.128 (10) | 0.151 (11) | 0.077 (7) | −0.090 (8) | 0.038 (7) | −0.027 (7) |
C43 | 0.151 (12) | 0.174 (12) | 0.084 (8) | −0.102 (10) | 0.049 (8) | −0.067 (8) |
C44 | 0.076 (6) | 0.101 (7) | 0.070 (6) | −0.040 (5) | 0.008 (5) | −0.024 (5) |
C45 | 0.072 (6) | 0.090 (6) | 0.056 (5) | −0.027 (5) | 0.005 (4) | −0.012 (5) |
C46 | 0.083 (6) | 0.079 (5) | 0.052 (5) | −0.019 (5) | 0.007 (4) | −0.007 (4) |
C47 | 0.048 (4) | 0.046 (3) | 0.053 (4) | 0.004 (3) | 0.002 (3) | 0.001 (3) |
C48 | 0.061 (5) | 0.046 (4) | 0.043 (4) | 0.000 (3) | 0.011 (3) | 0.001 (3) |
C49 | 0.054 (4) | 0.043 (3) | 0.046 (4) | 0.002 (3) | 0.009 (3) | 0.001 (3) |
C50 | 0.073 (6) | 0.064 (5) | 0.059 (5) | −0.018 (4) | 0.005 (4) | −0.002 (4) |
C51 | 0.096 (7) | 0.078 (6) | 0.051 (5) | −0.023 (5) | 0.021 (5) | 0.000 (4) |
C52 | 0.090 (6) | 0.070 (5) | 0.046 (4) | −0.017 (5) | 0.014 (4) | −0.003 (4) |
Pb1—O1 | 2.582 (5) | C13—H13 | 0.9300 |
Pb1—O2 | 2.824 (5) | C15—C16 | 1.384 (12) |
Pb1—O5i | 2.818 (6) | C15—H15 | 0.9300 |
Pb1—N1 | 2.672 (6) | C16—C17 | 1.327 (11) |
Pb1—N2 | 2.570 (6) | C16—H16 | 0.9300 |
Pb1—N5 | 2.612 (6) | C17—C18 | 1.398 (10) |
Pb1—N6 | 2.506 (6) | C17—H17 | 0.9300 |
O1—C1 | 1.255 (9) | C18—C19 | 1.388 (9) |
O2—C1 | 1.257 (9) | C18—C20 | 1.446 (10) |
O3—C8 | 1.371 (10) | C19—C30 | 1.464 (9) |
O3—C5 | 1.397 (9) | C20—C28 | 1.376 (9) |
O4—C14 | 1.243 (10) | C21—C22 | 1.466 (11) |
O5—C14 | 1.184 (10) | C22—C27 | 1.357 (12) |
O6—C25 | 1.398 (10) | C22—C23 | 1.360 (10) |
O6—H6O | 0.8200 | C23—C24 | 1.402 (11) |
O7—C44 | 1.385 (10) | C23—H23 | 0.9300 |
O7—H7O | 0.8201 | C24—C25 | 1.339 (12) |
O1W—H1W1 | 0.8199 | C24—H24 | 0.9300 |
O1W—H1W2 | 0.8200 | C25—C26 | 1.344 (12) |
O2W—H2W1 | 0.8199 | C26—C27 | 1.383 (13) |
O2W—H2W2 | 0.8201 | C26—H26 | 0.9300 |
N1—C15 | 1.335 (10) | C27—H27 | 0.9300 |
N1—C19 | 1.339 (9) | C28—C29 | 1.434 (9) |
N2—C33 | 1.327 (9) | C29—C31 | 1.393 (10) |
N2—C30 | 1.364 (9) | C29—C30 | 1.413 (10) |
N3—C21 | 1.343 (10) | C31—C32 | 1.344 (11) |
N3—C20 | 1.387 (9) | C31—H31 | 0.9300 |
N3—H3N | 0.8600 | C32—C33 | 1.377 (11) |
N4—C21 | 1.335 (9) | C32—H32 | 0.9300 |
N4—C28 | 1.367 (9) | C33—H33 | 0.9300 |
N5—C34 | 1.325 (10) | C34—C35 | 1.381 (11) |
N5—C38 | 1.353 (8) | C34—H34 | 0.9300 |
N6—C52 | 1.330 (9) | C35—C36 | 1.356 (10) |
N6—C49 | 1.352 (8) | C35—H35 | 0.9300 |
N7—C40 | 1.364 (9) | C36—C37 | 1.417 (9) |
N7—C39 | 1.371 (8) | C36—H36 | 0.9300 |
N7—H7N | 0.8600 | C37—C39 | 1.410 (9) |
N8—C40 | 1.318 (9) | C37—C38 | 1.417 (9) |
N8—C47 | 1.382 (9) | C38—C49 | 1.454 (9) |
C1—C2 | 1.524 (11) | C39—C47 | 1.371 (10) |
C2—C3 | 1.376 (11) | C40—C41 | 1.466 (10) |
C2—C7 | 1.427 (11) | C41—C42 | 1.355 (12) |
C3—C4 | 1.423 (11) | C41—C46 | 1.368 (11) |
C3—H3 | 0.9300 | C42—C43 | 1.390 (13) |
C4—C5 | 1.364 (12) | C42—H42 | 0.9300 |
C4—H4 | 0.9300 | C43—C44 | 1.363 (13) |
C5—C6 | 1.383 (12) | C43—H43 | 0.9300 |
C6—C7 | 1.357 (11) | C44—C45 | 1.330 (12) |
C6—H6 | 0.9300 | C45—C46 | 1.405 (11) |
C7—H7 | 0.9300 | C45—H45 | 0.9300 |
C8—C13 | 1.369 (13) | C46—H46 | 0.9300 |
C8—C9 | 1.378 (13) | C47—C48 | 1.440 (9) |
C9—C10 | 1.399 (13) | C48—C50 | 1.390 (11) |
C9—H9 | 0.9300 | C48—C49 | 1.404 (10) |
C10—C11 | 1.407 (12) | C50—C51 | 1.363 (11) |
C10—H10 | 0.9300 | C50—H50 | 0.9300 |
C11—C12 | 1.415 (13) | C51—C52 | 1.403 (12) |
C11—C14 | 1.539 (12) | C51—H51 | 0.9300 |
C12—C13 | 1.364 (13) | C52—H52 | 0.9300 |
C12—H12 | 0.9300 | ||
N6—Pb1—N2 | 74.7 (2) | N1—C19—C18 | 121.8 (6) |
N6—Pb1—O1 | 75.8 (2) | N1—C19—C30 | 117.6 (6) |
N2—Pb1—O1 | 128.6 (2) | C18—C19—C30 | 120.6 (7) |
N6—Pb1—N5 | 63.86 (18) | C28—C20—N3 | 105.2 (6) |
N2—Pb1—N5 | 83.28 (19) | C28—C20—C18 | 123.3 (6) |
O1—Pb1—N5 | 118.63 (18) | N3—C20—C18 | 131.4 (6) |
N6—Pb1—N1 | 82.70 (18) | N4—C21—N3 | 111.7 (6) |
N2—Pb1—N1 | 62.47 (18) | N4—C21—C22 | 124.4 (7) |
O1—Pb1—N1 | 72.93 (18) | N3—C21—C22 | 123.9 (7) |
N5—Pb1—N1 | 137.72 (19) | C27—C22—C23 | 117.0 (8) |
N6—Pb1—O5i | 127.2 (2) | C27—C22—C21 | 121.6 (8) |
N2—Pb1—O5i | 75.4 (2) | C23—C22—C21 | 121.4 (8) |
O1—Pb1—O5i | 153.4 (3) | C22—C23—C24 | 120.4 (8) |
N5—Pb1—O5i | 70.28 (19) | C22—C23—H23 | 119.8 |
N1—Pb1—O5i | 118.9 (2) | C24—C23—H23 | 119.8 |
N6—Pb1—O2 | 76.57 (18) | C25—C24—C23 | 119.7 (8) |
N2—Pb1—O2 | 150.48 (19) | C25—C24—H24 | 120.1 |
O1—Pb1—O2 | 47.62 (16) | C23—C24—H24 | 120.1 |
N5—Pb1—O2 | 78.26 (17) | C24—C25—C26 | 121.6 (9) |
N1—Pb1—O2 | 120.01 (17) | C24—C25—O6 | 119.8 (8) |
O5i—Pb1—O2 | 118.49 (19) | C26—C25—O6 | 118.6 (9) |
C1—O1—Pb1 | 99.6 (5) | C25—C26—C27 | 117.5 (10) |
C1—O2—Pb1 | 88.1 (4) | C25—C26—H26 | 121.2 |
C8—O3—C5 | 115.1 (7) | C27—C26—H26 | 121.2 |
C25—O6—H6O | 120.7 | C22—C27—C26 | 123.6 (9) |
C44—O7—H7O | 120.1 | C22—C27—H27 | 118.2 |
H1W1—O1W—H1W2 | 109.8 | C26—C27—H27 | 118.2 |
H2W1—O2W—H2W2 | 108.8 | N4—C28—C20 | 110.4 (6) |
C15—N1—C19 | 118.1 (6) | N4—C28—C29 | 128.5 (7) |
C15—N1—Pb1 | 122.1 (5) | C20—C28—C29 | 121.0 (7) |
C19—N1—Pb1 | 119.7 (4) | C31—C29—C30 | 118.4 (7) |
C33—N2—C30 | 118.1 (6) | C31—C29—C28 | 124.7 (7) |
C33—N2—Pb1 | 119.4 (5) | C30—C29—C28 | 116.8 (6) |
C30—N2—Pb1 | 122.3 (5) | N2—C30—C29 | 120.7 (6) |
C21—N3—C20 | 107.3 (6) | N2—C30—C19 | 117.8 (6) |
C21—N3—H3N | 126.3 | C29—C30—C19 | 121.5 (6) |
C20—N3—H3N | 126.3 | C32—C31—C29 | 119.7 (8) |
C21—N4—C28 | 105.4 (6) | C32—C31—H31 | 120.1 |
C34—N5—C38 | 118.5 (6) | C29—C31—H31 | 120.1 |
C34—N5—Pb1 | 123.0 (5) | C31—C32—C33 | 119.4 (8) |
C38—N5—Pb1 | 118.3 (4) | C31—C32—H32 | 120.3 |
C52—N6—C49 | 118.1 (7) | C33—C32—H32 | 120.3 |
C52—N6—Pb1 | 119.4 (5) | N2—C33—C32 | 123.6 (8) |
C49—N6—Pb1 | 122.5 (5) | N2—C33—H33 | 118.2 |
C40—N7—C39 | 107.1 (6) | C32—C33—H33 | 118.2 |
C40—N7—H7N | 126.5 | N5—C34—C35 | 123.4 (7) |
C39—N7—H7N | 126.5 | N5—C34—H34 | 118.3 |
C40—N8—C47 | 104.0 (6) | C35—C34—H34 | 118.3 |
O2—C1—O1 | 121.6 (7) | C36—C35—C34 | 120.2 (7) |
O2—C1—C2 | 121.0 (7) | C36—C35—H35 | 119.9 |
O1—C1—C2 | 117.3 (7) | C34—C35—H35 | 119.9 |
C3—C2—C7 | 119.9 (8) | C35—C36—C37 | 118.4 (6) |
C3—C2—C1 | 120.5 (8) | C35—C36—H36 | 120.8 |
C7—C2—C1 | 119.5 (8) | C37—C36—H36 | 120.8 |
C2—C3—C4 | 119.3 (8) | C39—C37—C38 | 116.3 (6) |
C2—C3—H3 | 120.3 | C39—C37—C36 | 125.5 (6) |
C4—C3—H3 | 120.3 | C38—C37—C36 | 118.2 (6) |
C5—C4—C3 | 119.5 (8) | N5—C38—C37 | 121.4 (6) |
C5—C4—H4 | 120.2 | N5—C38—C49 | 117.9 (6) |
C3—C4—H4 | 120.2 | C37—C38—C49 | 120.8 (6) |
C4—C5—C6 | 120.9 (8) | N7—C39—C47 | 105.1 (6) |
C4—C5—O3 | 120.1 (8) | N7—C39—C37 | 130.6 (6) |
C6—C5—O3 | 119.0 (9) | C47—C39—C37 | 124.3 (6) |
C7—C6—C5 | 121.1 (9) | N8—C40—N7 | 112.5 (6) |
C7—C6—H6 | 119.4 | N8—C40—C41 | 125.7 (7) |
C5—C6—H6 | 119.4 | N7—C40—C41 | 121.7 (7) |
C6—C7—C2 | 119.2 (9) | C42—C41—C46 | 117.0 (8) |
C6—C7—H7 | 120.4 | C42—C41—C40 | 121.2 (8) |
C2—C7—H7 | 120.4 | C46—C41—C40 | 121.8 (7) |
O3—C8—C13 | 119.9 (10) | C41—C42—C43 | 122.4 (9) |
O3—C8—C9 | 119.8 (9) | C41—C42—H42 | 118.8 |
C13—C8—C9 | 120.2 (9) | C43—C42—H42 | 118.8 |
C8—C9—C10 | 119.6 (10) | C44—C43—C42 | 118.6 (10) |
C8—C9—H9 | 120.2 | C44—C43—H43 | 120.7 |
C10—C9—H9 | 120.2 | C42—C43—H43 | 120.7 |
C9—C10—C11 | 120.4 (10) | C45—C44—C43 | 121.1 (9) |
C9—C10—H10 | 119.8 | C45—C44—O7 | 122.6 (8) |
C11—C10—H10 | 119.8 | C43—C44—O7 | 116.3 (9) |
C10—C11—C12 | 117.9 (9) | C44—C45—C46 | 119.2 (8) |
C10—C11—C14 | 119.6 (9) | C44—C45—H45 | 120.4 |
C12—C11—C14 | 122.5 (8) | C46—C45—H45 | 120.4 |
C13—C12—C11 | 120.2 (9) | C41—C46—C45 | 121.6 (8) |
C13—C12—H12 | 119.9 | C41—C46—H46 | 119.2 |
C11—C12—H12 | 119.9 | C45—C46—H46 | 119.2 |
C8—C13—C12 | 121.6 (9) | C39—C47—N8 | 111.3 (6) |
C8—C13—H13 | 119.2 | C39—C47—C48 | 120.2 (6) |
C12—C13—H13 | 119.2 | N8—C47—C48 | 128.4 (7) |
O5—C14—O4 | 123.5 (9) | C50—C48—C49 | 118.3 (7) |
O5—C14—C11 | 118.2 (9) | C50—C48—C47 | 123.8 (7) |
O4—C14—C11 | 116.7 (8) | C49—C48—C47 | 117.8 (6) |
N1—C15—C16 | 122.5 (8) | N6—C49—C48 | 122.1 (6) |
N1—C15—H15 | 118.7 | N6—C49—C38 | 117.4 (6) |
C16—C15—H15 | 118.7 | C48—C49—C38 | 120.5 (6) |
C17—C16—C15 | 119.6 (8) | C51—C50—C48 | 119.7 (8) |
C17—C16—H16 | 120.2 | C51—C50—H50 | 120.2 |
C15—C16—H16 | 120.2 | C48—C50—H50 | 120.2 |
C16—C17—C18 | 119.5 (7) | C50—C51—C52 | 118.8 (8) |
C16—C17—H17 | 120.2 | C50—C51—H51 | 120.6 |
C18—C17—H17 | 120.2 | C52—C51—H51 | 120.6 |
C19—C18—C17 | 118.3 (7) | N6—C52—C51 | 123.0 (7) |
C19—C18—C20 | 116.7 (6) | N6—C52—H52 | 118.5 |
C17—C18—C20 | 125.0 (7) | C51—C52—H52 | 118.5 |
N6—Pb1—O1—C1 | −75.1 (6) | C19—C18—C20—N3 | −177.2 (7) |
N2—Pb1—O1—C1 | −131.5 (6) | C17—C18—C20—N3 | 2.1 (13) |
N5—Pb1—O1—C1 | −26.1 (6) | C28—N4—C21—N3 | −0.9 (9) |
N1—Pb1—O1—C1 | −161.7 (6) | C28—N4—C21—C22 | 178.3 (7) |
O5i—Pb1—O1—C1 | 77.3 (7) | C20—N3—C21—N4 | 0.3 (9) |
O2—Pb1—O1—C1 | 9.6 (5) | C20—N3—C21—C22 | −178.8 (7) |
N6—Pb1—O2—C1 | 73.4 (5) | N4—C21—C22—C27 | 5.3 (14) |
N2—Pb1—O2—C1 | 86.6 (6) | N3—C21—C22—C27 | −175.7 (9) |
O1—Pb1—O2—C1 | −9.4 (5) | N4—C21—C22—C23 | −170.4 (8) |
N5—Pb1—O2—C1 | 139.0 (5) | N3—C21—C22—C23 | 8.6 (13) |
N1—Pb1—O2—C1 | 0.2 (6) | C27—C22—C23—C24 | 4.4 (13) |
O5i—Pb1—O2—C1 | −161.3 (5) | C21—C22—C23—C24 | −179.8 (8) |
N6—Pb1—N1—C15 | −102.2 (6) | C22—C23—C24—C25 | −3.5 (13) |
N2—Pb1—N1—C15 | −178.7 (6) | C23—C24—C25—C26 | 1.0 (16) |
O1—Pb1—N1—C15 | −24.9 (6) | C23—C24—C25—O6 | −177.7 (8) |
N5—Pb1—N1—C15 | −139.0 (6) | C24—C25—C26—C27 | 0.5 (19) |
O5i—Pb1—N1—C15 | 129.1 (6) | O6—C25—C26—C27 | 179.1 (11) |
O2—Pb1—N1—C15 | −32.3 (6) | C23—C22—C27—C26 | −3.0 (18) |
N6—Pb1—N1—C19 | 80.2 (5) | C21—C22—C27—C26 | −178.8 (11) |
N2—Pb1—N1—C19 | 3.8 (5) | C25—C26—C27—C22 | 1 (2) |
O1—Pb1—N1—C19 | 157.5 (6) | C21—N4—C28—C20 | 1.1 (9) |
N5—Pb1—N1—C19 | 43.4 (6) | C21—N4—C28—C29 | −175.5 (8) |
O5i—Pb1—N1—C19 | −48.5 (6) | N3—C20—C28—N4 | −0.9 (8) |
O2—Pb1—N1—C19 | 150.1 (5) | C18—C20—C28—N4 | −178.6 (6) |
N6—Pb1—N2—C33 | 90.8 (7) | N3—C20—C28—C29 | 176.0 (7) |
O1—Pb1—N2—C33 | 147.7 (6) | C18—C20—C28—C29 | −1.7 (11) |
N5—Pb1—N2—C33 | 26.1 (6) | N4—C28—C29—C31 | −4.0 (13) |
N1—Pb1—N2—C33 | −179.5 (7) | C20—C28—C29—C31 | 179.7 (8) |
O5i—Pb1—N2—C33 | −45.2 (6) | N4—C28—C29—C30 | 178.4 (7) |
O2—Pb1—N2—C33 | 77.5 (7) | C20—C28—C29—C30 | 2.2 (11) |
N6—Pb1—N2—C30 | −93.5 (6) | C33—N2—C30—C29 | −0.8 (11) |
O1—Pb1—N2—C30 | −36.6 (6) | Pb1—N2—C30—C29 | −176.5 (5) |
N5—Pb1—N2—C30 | −158.2 (6) | C33—N2—C30—C19 | 179.5 (7) |
N1—Pb1—N2—C30 | −3.8 (5) | Pb1—N2—C30—C19 | 3.8 (9) |
O5i—Pb1—N2—C30 | 130.5 (6) | C31—C29—C30—N2 | 1.7 (11) |
O2—Pb1—N2—C30 | −106.8 (6) | C28—C29—C30—N2 | 179.4 (7) |
N6—Pb1—N5—C34 | 178.3 (6) | C31—C29—C30—C19 | −178.6 (7) |
N2—Pb1—N5—C34 | −105.6 (6) | C28—C29—C30—C19 | −0.9 (10) |
O1—Pb1—N5—C34 | 123.7 (6) | N1—C19—C30—N2 | 0.0 (10) |
N1—Pb1—N5—C34 | −140.3 (5) | C18—C19—C30—N2 | 178.7 (7) |
O5i—Pb1—N5—C34 | −28.7 (6) | N1—C19—C30—C29 | −179.7 (7) |
O2—Pb1—N5—C34 | 97.6 (6) | C18—C19—C30—C29 | −1.0 (10) |
N6—Pb1—N5—C38 | 3.3 (4) | C30—C29—C31—C32 | −2.8 (14) |
N2—Pb1—N5—C38 | 79.5 (5) | C28—C29—C31—C32 | 179.6 (9) |
O1—Pb1—N5—C38 | −51.2 (5) | C29—C31—C32—C33 | 3.0 (16) |
N1—Pb1—N5—C38 | 44.7 (6) | C30—N2—C33—C32 | 1.0 (14) |
O5i—Pb1—N5—C38 | 156.4 (5) | Pb1—N2—C33—C32 | 176.8 (8) |
O2—Pb1—N5—C38 | −77.3 (5) | C31—C32—C33—N2 | −2.1 (17) |
N2—Pb1—N6—C52 | 88.8 (6) | C38—N5—C34—C35 | −0.2 (11) |
O1—Pb1—N6—C52 | −48.7 (6) | Pb1—N5—C34—C35 | −175.1 (6) |
N5—Pb1—N6—C52 | 178.8 (7) | N5—C34—C35—C36 | −0.4 (13) |
N1—Pb1—N6—C52 | 25.4 (6) | C34—C35—C36—C37 | 0.8 (11) |
O5i—Pb1—N6—C52 | 146.4 (6) | C35—C36—C37—C39 | 178.4 (7) |
O2—Pb1—N6—C52 | −97.9 (6) | C35—C36—C37—C38 | −0.7 (10) |
N2—Pb1—N6—C49 | −91.9 (5) | C34—N5—C38—C37 | 0.3 (10) |
O1—Pb1—N6—C49 | 130.5 (6) | Pb1—N5—C38—C37 | 175.4 (5) |
N5—Pb1—N6—C49 | −1.9 (5) | C34—N5—C38—C49 | −179.7 (6) |
N1—Pb1—N6—C49 | −155.3 (5) | Pb1—N5—C38—C49 | −4.5 (8) |
O5i—Pb1—N6—C49 | −34.3 (6) | C39—C37—C38—N5 | −179.1 (6) |
O2—Pb1—N6—C49 | 81.4 (5) | C36—C37—C38—N5 | 0.2 (10) |
Pb1—O2—C1—O1 | 17.0 (9) | C39—C37—C38—C49 | 0.9 (9) |
Pb1—O2—C1—C2 | −159.6 (8) | C36—C37—C38—C49 | −179.9 (6) |
Pb1—O1—C1—O2 | −18.9 (10) | C40—N7—C39—C47 | 0.9 (8) |
Pb1—O1—C1—C2 | 157.8 (6) | C40—N7—C39—C37 | −177.5 (7) |
O2—C1—C2—C3 | −18.4 (13) | C38—C37—C39—N7 | 175.5 (7) |
O1—C1—C2—C3 | 164.8 (8) | C36—C37—C39—N7 | −3.7 (12) |
O2—C1—C2—C7 | 158.8 (8) | C38—C37—C39—C47 | −2.6 (10) |
O1—C1—C2—C7 | −18.0 (12) | C36—C37—C39—C47 | 178.2 (7) |
C7—C2—C3—C4 | 0.5 (13) | C47—N8—C40—N7 | 0.8 (8) |
C1—C2—C3—C4 | 177.7 (7) | C47—N8—C40—C41 | −175.6 (7) |
C2—C3—C4—C5 | 0.7 (13) | C39—N7—C40—N8 | −1.1 (9) |
C3—C4—C5—C6 | −0.4 (14) | C39—N7—C40—C41 | 175.5 (7) |
C3—C4—C5—O3 | 177.3 (8) | N8—C40—C41—C42 | 164.3 (10) |
C8—O3—C5—C4 | 52.7 (13) | N7—C40—C41—C42 | −11.8 (13) |
C8—O3—C5—C6 | −129.6 (10) | N8—C40—C41—C46 | −15.6 (13) |
C4—C5—C6—C7 | −1.1 (16) | N7—C40—C41—C46 | 168.3 (8) |
O3—C5—C6—C7 | −178.8 (9) | C46—C41—C42—C43 | 3.0 (19) |
C5—C6—C7—C2 | 2.3 (15) | C40—C41—C42—C43 | −177.0 (12) |
C3—C2—C7—C6 | −2.0 (14) | C41—C42—C43—C44 | −4 (2) |
C1—C2—C7—C6 | −179.2 (9) | C42—C43—C44—C45 | 3 (2) |
C5—O3—C8—C13 | −126.1 (10) | C42—C43—C44—O7 | −178.0 (12) |
C5—O3—C8—C9 | 58.3 (13) | C43—C44—C45—C46 | 0.4 (18) |
O3—C8—C9—C10 | −179.7 (10) | O7—C44—C45—C46 | −178.9 (10) |
C13—C8—C9—C10 | 4.6 (16) | C42—C41—C46—C45 | 0.2 (15) |
C8—C9—C10—C11 | −2.4 (17) | C40—C41—C46—C45 | −179.9 (8) |
C9—C10—C11—C12 | −1.1 (16) | C44—C45—C46—C41 | −1.9 (15) |
C9—C10—C11—C14 | 178.9 (10) | N7—C39—C47—N8 | −0.4 (8) |
C10—C11—C12—C13 | 2.5 (14) | C37—C39—C47—N8 | 178.1 (6) |
C14—C11—C12—C13 | −177.5 (10) | N7—C39—C47—C48 | −177.4 (6) |
O3—C8—C13—C12 | −178.9 (9) | C37—C39—C47—C48 | 1.0 (11) |
C9—C8—C13—C12 | −3.3 (16) | C40—N8—C47—C39 | −0.2 (8) |
C11—C12—C13—C8 | −0.4 (15) | C40—N8—C47—C48 | 176.5 (7) |
C10—C11—C14—O5 | 179.6 (11) | C39—C47—C48—C50 | 178.5 (7) |
C12—C11—C14—O5 | −0.4 (16) | N8—C47—C48—C50 | 2.0 (12) |
C10—C11—C14—O4 | −13.9 (15) | C39—C47—C48—C49 | 2.3 (10) |
C12—C11—C14—O4 | 166.1 (10) | N8—C47—C48—C49 | −174.1 (7) |
C19—N1—C15—C16 | −1.5 (12) | C52—N6—C49—C48 | 0.2 (11) |
Pb1—N1—C15—C16 | −179.1 (7) | Pb1—N6—C49—C48 | −179.1 (5) |
N1—C15—C16—C17 | 1.9 (14) | C52—N6—C49—C38 | 179.8 (7) |
C15—C16—C17—C18 | −1.0 (13) | Pb1—N6—C49—C38 | 0.5 (8) |
C16—C17—C18—C19 | −0.4 (12) | C50—C48—C49—N6 | −0.7 (11) |
C16—C17—C18—C20 | −179.6 (8) | C47—C48—C49—N6 | 175.6 (6) |
C15—N1—C19—C18 | 0.1 (11) | C50—C48—C49—C38 | 179.7 (7) |
Pb1—N1—C19—C18 | 177.8 (5) | C47—C48—C49—C38 | −4.0 (10) |
C15—N1—C19—C30 | 178.8 (7) | N5—C38—C49—N6 | 2.7 (9) |
Pb1—N1—C19—C30 | −3.5 (8) | C37—C38—C49—N6 | −177.2 (6) |
C17—C18—C19—N1 | 0.8 (11) | N5—C38—C49—C48 | −177.6 (6) |
C20—C18—C19—N1 | −179.8 (6) | C37—C38—C49—C48 | 2.4 (10) |
C17—C18—C19—C30 | −177.9 (7) | C49—C48—C50—C51 | 0.5 (12) |
C20—C18—C19—C30 | 1.5 (10) | C47—C48—C50—C51 | −175.6 (8) |
C21—N3—C20—C28 | 0.3 (8) | C48—C50—C51—C52 | 0.1 (14) |
C21—N3—C20—C18 | 177.8 (8) | C49—N6—C52—C51 | 0.5 (13) |
C19—C18—C20—C28 | −0.2 (11) | Pb1—N6—C52—C51 | 179.8 (7) |
C17—C18—C20—C28 | 179.1 (7) | C50—C51—C52—N6 | −0.7 (14) |
Symmetry code: (i) −x+1/2, y−1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O2ii | 0.86 | 1.98 | 2.82 (1) | 166 |
N7—H7N···O4iii | 0.86 | 1.97 | 2.81 (1) | 166 |
O1W—H1W1···N4 | 0.82 | 2.00 | 2.82 (1) | 174 |
O1W—H1W2···O6iv | 0.82 | 2.37 | 2.57 (1) | 95 |
O2W—H2W1···N8 | 0.82 | 2.00 | 2.79 (1) | 160 |
O2W—H2W2···O3v | 0.82 | 2.27 | 3.06 (1) | 160 |
Symmetry codes: (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y, −z+1; (v) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Pb(C14H8O5)(C19H12N4O)2]·2H2O |
Mr | 1124.08 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 10.767 (4), 29.916 (7), 13.688 (4) |
β (°) | 97.70 (1) |
V (Å3) | 4369 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.93 |
Crystal size (mm) | 0.33 × 0.24 × 0.21 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.188, 0.492 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 42355, 9977, 6235 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.168, 1.02 |
No. of reflections | 9977 |
No. of parameters | 631 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.52, −1.10 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
Pb1—O1 | 2.582 (5) | Pb1—N2 | 2.570 (6) |
Pb1—O2 | 2.824 (5) | Pb1—N5 | 2.612 (6) |
Pb1—O5i | 2.818 (6) | Pb1—N6 | 2.506 (6) |
Pb1—N1 | 2.672 (6) |
Symmetry code: (i) −x+1/2, y−1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O2ii | 0.86 | 1.98 | 2.82 (1) | 166 |
N7—H7N···O4iii | 0.86 | 1.97 | 2.81 (1) | 166 |
O1W—H1W1···N4 | 0.82 | 2.00 | 2.82 (1) | 174 |
O1W—H1W2···O6iv | 0.82 | 2.37 | 2.57 (1) | 95 |
O2W—H2W1···N8 | 0.82 | 2.00 | 2.79 (1) | 160 |
O2W—H2W2···O3v | 0.82 | 2.27 | 3.06 (1) | 160 |
Symmetry codes: (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y, −z+1; (v) −x+1, −y+1, −z+1. |
Acknowledgements
We thank Xi'an Modern Chemistry Research Institute and the University of Malaya for supporting this work.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
Xu, M.-L., Zhou, R., Wang, G.-Y. & Ng, S. W. (2008). Acta Cryst. E64, m710–m711. Web of Science CSD CrossRef IUCr Journals Google Scholar
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The 4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol N-heterocycle furnishes adducts with metal dicarboxylates (Xu et al., 2008).
The carboxylate dianion in the title chain compound uses one carboxyl –CO2 group to O,O'-chelate to the lead(II) atom and uses its other carboxyl end to bind to another lead atom in a unidentate manner. The lead atom exists in an undefined seven-coordinate geometry; the Pb—O distances range between 2.582 (5) and 2.824 (5) Å, and the Pb—N distances vary between 2.506 (6) and 2.672 (6) Å (Table 1). The lone-pair is stereochemically active. Adjacent chains are linked by intermolecular O—H···N, N—H···O and O—H···O hydrogen bonds (Table 2) that involve the lattice water molecules to form a three-dimensional network.