Bis(μ-2-sulfonatobenzoato)bis[(1,10-phenanthroline)­lead(II)] dihydrate

In the title centrosymmetric dimer, [Pb₂(sbc)₂(phen)₂]·2H₂O [sbc is the 2-sulfonatobenzoate dianion (C₇H₄O₅S) and phen is 1,10-phenanthroline (C₁₂H₈N₂)], each Pb^II ion is six-coordinated by four O atoms, viz. carboxyl­ate and sulfonate O atoms from two sbc anions, and two N atoms from a 1,10-phenanthroline ligand. One 1,10-phenanthroline ligand and the carboxyl­ate group of one sbc ligand are chelated to each Pb^II cation, and the sulfonate group of the other sbc unit is monodentate. One O atom of the chelated carboxyl­ate group also bridges to the other Pb^II cation, so that each pair of Pb^II ions is bridged by two sbc anions and has the same coordination environment, forming a dinuclear ring. Each pair of Pb^II ions is thus connected by two different kinds of bridges, namely a carboxyl­ate short bridge and a carboxyl­ate–sulfonate long bridge. There is also a special position of site symmetry at the centre of the two Pb^II cations.

S1. Comment

Lead(II) is capable of exhibiting variable coordination number and geometry with or without a stereochemically active lone pair of electrons (Wang & Vittal, 2003). Of these, a number of polymeric Pb^II compounds have been structurally characterized (Cecconi et al., 2003; Bridgewater & Parkin, 2000; Ying et al., 2003). The absence of crystal field-stabilization energy effects also allows Pb^II cations to adopt a range of different coordination geometries, not restricted to octahedral, tetrahedral or square-planar (Foreman et al., 2000). 2-Sulfobenzenecarboxylate (sbc) is a very interesting ligand, with both carboxylate and sulfonate as potential coordinating groups. It can form not only short bridges between metal ions via one carboxylate end or one sulfonate end, but also a long bridge via the benzene ring. Thus, we have selected the Pb-sbc system to extend this research and we present here the crystal structure of the title compound, [Pb(sbc)(phen)]₂·2H₂O, (I). \sch

In (I), each Pb^II ion coordinates to three O atoms from two carboxylate groups of two sbc anions, with a typical range of Pb—O(carboxylate) distances [2.574 (3)–2.595 (4) Å; Foreman et al., 2000], one sulfonate O atom from one sbc anion, with Pb—O distances of 2.646 (4) Å, and two N atoms from one 1,10-phenanthroline ligand, with Pb—N distances of 2.540 (4) and 2.569 (4) Å. The coordination numbers of the two Pb^II ions are equivalent, but although both Pb^II cations are six-coordinated, due to the absence of crystal field-stabilization energy effects, the coordination geometries of the Pb^II cations are not octahedral (Fig. 1). The two N atoms of 1,10-phenanthroline and two O atoms of the carboxylate are chelated to each Pb^II cation, and the sulfonate group of the other sbc is monodentate. One O atom of the chelated carboxylate group also bridges to the other Pb^II cation, with Pb—O distances of 2.734 (3) Å. Thus, each pair of Pb^II ions has the same coordination environment and is bridged by two sbc anions, forming a centrosymmetric dinuclear ring. Each pair of Pb^II ions is therefore connected by two different kinds of bridges, namely a carboxylate short bridge and a carboxylate-sulfonate long bridge. There is also a special position of 1 site symmetry at the centre of the two Pb^II cations.

The S1—O3, S1—O4 and S1—O5 distances are 1.469 (4), 1.465 (4) and 1.428 (4) Å, respectively, and all fall within the typical range of S—O bond distances in the sulfonate anion (1.40–1.49 Å; Onoda et al., 2001). The similarity of the three S—O bond distances suggests that strong conjugation of the sulfonate is predominant in (I). In addition, each sbc anion acts as a tetradentate ligand, connecting two Pb^II ions through its bridging and chelating carboxylate group and its monodentate sulfonate group. This coordination mode is quite different from that in the above-mentioned polymeric Pb^II compounds, in which the carboxylate groups are either bidentate chelating or monodentate bridging.

It should be noted that hydrogen-bonding interactions and π–π interactions play an important role in the solid-state structure of (I), as shown in Fig. 2. Adjacent units are connected by hydrogen-bond and π–π stacking, resulting in a packing framework stucture.

S2. Experimental

The title compound was synthesized by adding a solution of 1,10-phenanthroline (0.04 g, 0.2 mmol), 2-sulfobenzenecarboxylic acid (0.04 g, 0.2 mmol) and 2,2'-dithiosalicylic acid (0.06 g, 0.2 mmol) in dimethylformamide (10 ml) dropwise to a stirred solution of lead nitrate (0.07 g, 0.2 mmol) in water (10 ml) at 298 K. The reaction mixture was filtered and the filtrate allowed to stand for about 6 weeks until colourless prism crystals of (I) were obtained. Crystals suitable for X-ray diffraction were collected by filtration, washed with water and ethanol, and dried in air.

S3. Refinement

The water H atoms were refined subject to the restraint O—H = 0.82 (2) Å. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances of 0.93 Å and with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The coordination environment of the Pb^II ion in (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Atoms labelled with an asterisk (*) are at the symmetry position (2 − x, 1 − y, 1 − z).
	Fig. 2. A perspective view of the molecular packing of (I) along the a axis, illustrating the hydrogen-bonding and π–π interactions. Hydrogen-bonding interactions are shown as dashed lines and H atoms not involved in hydrogen bonds have been omitted for clarity.

Bis(µ-2-sulfobenzenecarboxylato)bis[(1,10-phenanthroline)lead(II)] dihydrate

Crystal data

[Pb2(C7H4O5S)2(C12H8N2)2]·2H2O	Z = 2
Mr = 605.57	F(000) = 576
Triclinic, P1	Dx = 2.151 Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3232 (7) Å	Cell parameters from 3352 reflections
b = 10.8613 (10) Å	θ = 2.3–25.3°
c = 12.0558 (11) Å	µ = 9.18 mm^−1
α = 97.280 (1)°	T = 298 K
β = 100.320 (2)°	Prism, colourless
γ = 91.150 (1)°	0.20 × 0.15 × 0.10 mm
V = 934.89 (15) Å^3

Data collection

Bruker APEX CCD area-detector diffractometer	3352 independent reflections
Radiation source: fine-focus sealed tube	3162 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ϕ and ω scans	θmax = 25.3°, θmin = 1.9°
Absorption correction: numerical (SADABS; Bruker, 2002)	h = −8→8
Tmin = 0.034, Tmax = 0.227	k = −13→12
6867 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0341P)^2 + 0.2266P] where P = (Fo^2 + 2Fc^2)/3
3352 reflections	(Δ/σ)max = 0.001
270 parameters	Δρmax = 1.75 e Å^−3
0 restraints	Δρmin = −0.60 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O6	0.8489 (9)	0.2030 (7)	0.0765 (5)	0.0880 (18)
Pb1	0.79333 (2)	0.605327 (14)	0.565670 (14)	0.02970 (8)
S1	0.48519 (17)	0.59828 (12)	0.31857 (11)	0.0378 (3)
O1	0.9269 (5)	0.5524 (3)	0.3827 (3)	0.0406 (8)
O3	0.5714 (5)	0.7016 (3)	0.4036 (3)	0.0421 (8)
O4	0.5278 (5)	0.4785 (3)	0.3587 (3)	0.0460 (9)
O5	0.2910 (6)	0.6107 (5)	0.2809 (4)	0.0726 (13)
N1	1.0069 (5)	0.7936 (3)	0.5696 (3)	0.0329 (9)
N2	0.7212 (5)	0.8020 (3)	0.6897 (3)	0.0342 (9)
C1	1.1442 (7)	0.7912 (5)	0.5113 (5)	0.0443 (13)
H1	1.1553	0.7198	0.4620	0.053*
C2	1.2725 (8)	0.8897 (5)	0.5200 (5)	0.0497 (14)
H2	1.3679	0.8834	0.4783	0.060*
C3	1.2562 (8)	0.9946 (5)	0.5900 (6)	0.0510 (14)
H3	1.3391	1.0621	0.5958	0.061*
C4	1.1125 (7)	1.0015 (5)	0.6545 (5)	0.0422 (12)
C5	1.0891 (9)	1.1089 (5)	0.7302 (6)	0.0633 (18)
H5	1.1720	1.1770	0.7394	0.076*
C6	0.9492 (10)	1.1136 (5)	0.7885 (6)	0.0615 (17)
H6	0.9360	1.1855	0.8367	0.074*
C7	0.8204 (8)	1.0110 (5)	0.7784 (5)	0.0462 (13)
C8	0.6732 (9)	1.0109 (5)	0.8386 (5)	0.0552 (15)
H8	0.6566	1.0801	0.8890	0.066*
C9	0.5534 (9)	0.9084 (5)	0.8229 (5)	0.0516 (14)
H9	0.4550	0.9072	0.8620	0.062*
C10	0.5833 (8)	0.8068 (5)	0.7471 (5)	0.0435 (12)
H10	0.5013	0.7380	0.7360	0.052*
C11	0.9914 (7)	0.8976 (4)	0.6410 (4)	0.0352 (11)
C12	0.8402 (7)	0.9032 (4)	0.7041 (4)	0.0335 (10)
C13	0.8885 (6)	0.4964 (5)	0.2831 (4)	0.0339 (11)
C14	0.7694 (7)	0.5571 (4)	0.1918 (4)	0.0326 (10)
C15	0.5935 (7)	0.6029 (4)	0.1977 (4)	0.0321 (10)
C16	0.4948 (7)	0.6532 (5)	0.1064 (5)	0.0425 (12)
H16	0.3752	0.6791	0.1090	0.051*
C17	0.5708 (8)	0.6652 (5)	0.0125 (5)	0.0487 (14)
H17	0.5047	0.7019	−0.0470	0.058*
C18	0.7449 (9)	0.6230 (6)	0.0059 (5)	0.0501 (14)
H18	0.7962	0.6312	−0.0581	0.060*
C19	0.8436 (8)	0.5685 (5)	0.0942 (5)	0.0418 (12)
H19	0.9605	0.5391	0.0887	0.050*
O2	0.9549 (5)	0.3944 (3)	0.2529 (3)	0.0468 (9)
H6A	0.885 (15)	0.276 (11)	0.123 (10)	0.14 (4)*
H6B	0.89 (2)	0.136 (14)	0.107 (13)	0.24 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O6	0.099 (4)	0.079 (4)	0.066 (3)	0.006 (3)	−0.015 (3)	−0.022 (3)
Pb1	0.03257 (11)	0.02643 (11)	0.02964 (12)	−0.00129 (7)	0.00979 (8)	−0.00342 (7)
S1	0.0344 (6)	0.0425 (7)	0.0372 (7)	−0.0036 (5)	0.0131 (5)	−0.0004 (6)
O1	0.0406 (19)	0.051 (2)	0.0289 (19)	0.0055 (16)	0.0103 (15)	−0.0053 (16)
O3	0.054 (2)	0.0365 (19)	0.034 (2)	0.0015 (17)	0.0135 (17)	−0.0068 (16)
O4	0.060 (2)	0.0359 (19)	0.045 (2)	−0.0084 (17)	0.0216 (19)	0.0020 (17)
O5	0.042 (2)	0.111 (4)	0.067 (3)	0.004 (2)	0.017 (2)	0.009 (3)
N1	0.038 (2)	0.029 (2)	0.032 (2)	−0.0002 (17)	0.0090 (18)	−0.0005 (17)
N2	0.039 (2)	0.030 (2)	0.034 (2)	0.0045 (17)	0.0108 (18)	−0.0012 (17)
C1	0.044 (3)	0.038 (3)	0.053 (4)	0.002 (2)	0.019 (3)	0.001 (3)
C2	0.043 (3)	0.050 (3)	0.059 (4)	−0.003 (3)	0.020 (3)	0.004 (3)
C3	0.040 (3)	0.043 (3)	0.068 (4)	−0.009 (2)	0.007 (3)	0.008 (3)
C4	0.044 (3)	0.031 (3)	0.049 (3)	−0.005 (2)	0.007 (2)	0.000 (2)
C5	0.063 (4)	0.035 (3)	0.086 (5)	−0.017 (3)	0.014 (4)	−0.013 (3)
C6	0.072 (4)	0.035 (3)	0.073 (5)	−0.003 (3)	0.016 (4)	−0.017 (3)
C7	0.059 (3)	0.035 (3)	0.042 (3)	0.001 (2)	0.009 (3)	−0.005 (2)
C8	0.075 (4)	0.042 (3)	0.050 (4)	0.006 (3)	0.026 (3)	−0.014 (3)
C9	0.064 (4)	0.051 (3)	0.046 (3)	0.012 (3)	0.031 (3)	0.001 (3)
C10	0.048 (3)	0.041 (3)	0.043 (3)	0.000 (2)	0.017 (3)	0.002 (2)
C11	0.040 (3)	0.031 (2)	0.033 (3)	−0.002 (2)	0.007 (2)	−0.001 (2)
C12	0.044 (3)	0.026 (2)	0.029 (3)	0.001 (2)	0.006 (2)	−0.0017 (19)
C13	0.033 (2)	0.040 (3)	0.028 (3)	−0.002 (2)	0.008 (2)	0.000 (2)
C14	0.039 (3)	0.028 (2)	0.029 (3)	−0.001 (2)	0.006 (2)	−0.0043 (19)
C15	0.036 (2)	0.029 (2)	0.031 (3)	−0.0027 (19)	0.009 (2)	−0.002 (2)
C16	0.034 (3)	0.046 (3)	0.046 (3)	0.001 (2)	0.004 (2)	0.006 (3)
C17	0.061 (4)	0.049 (3)	0.037 (3)	0.006 (3)	0.003 (3)	0.017 (3)
C18	0.064 (4)	0.055 (3)	0.036 (3)	0.005 (3)	0.018 (3)	0.010 (3)
C19	0.045 (3)	0.046 (3)	0.036 (3)	0.004 (2)	0.012 (2)	0.003 (2)
O2	0.061 (2)	0.0337 (19)	0.041 (2)	0.0103 (17)	0.0004 (18)	−0.0045 (16)

Geometric parameters (Å, º)

O6—H6A	0.92 (12)	C5—C6	1.341 (9)
O6—H6B	0.88 (14)	C5—H5	0.9300
Pb1—N1	2.540 (4)	C6—C7	1.424 (8)
Pb1—N2	2.569 (4)	C6—H6	0.9300
Pb1—O1	2.574 (3)	C7—C8	1.403 (8)
Pb1—O2^i	2.595 (4)	C7—C12	1.408 (7)
Pb1—O3	2.646 (4)	C8—C9	1.376 (8)
Pb1—O1^i	2.734 (3)	C8—H8	0.9300
S1—O5	1.428 (4)	C9—C10	1.388 (8)
S1—O4	1.465 (4)	C9—H9	0.9300
S1—O3	1.469 (4)	C10—H10	0.9300
S1—C15	1.785 (5)	C11—C12	1.450 (7)
O1—C13	1.256 (6)	C13—O2	1.256 (6)
O1—Pb1^i	2.734 (3)	C13—C14	1.507 (7)
N1—C1	1.324 (6)	C14—C19	1.400 (7)
N1—C11	1.350 (6)	C14—C15	1.400 (7)
N2—C10	1.321 (6)	C15—C16	1.384 (7)
N2—C12	1.363 (6)	C16—C17	1.367 (8)
C1—C2	1.391 (8)	C16—H16	0.9300
C1—H1	0.9300	C17—C18	1.376 (8)
C2—C3	1.351 (8)	C17—H17	0.9300
C2—H2	0.9300	C18—C19	1.380 (9)
C3—C4	1.413 (8)	C18—H18	0.9300
C3—H3	0.9300	C19—H19	0.9300
C4—C11	1.396 (7)	O2—Pb1^i	2.595 (4)
C4—C5	1.421 (8)
H6A—O6—H6B	114 (10)	C6—C5—H5	119.5
N1—Pb1—N2	65.03 (12)	C4—C5—H5	119.5
N1—Pb1—O1	77.52 (12)	C5—C6—C7	121.5 (6)
N2—Pb1—O1	137.24 (12)	C5—C6—H6	119.2
N1—Pb1—O2^i	74.86 (12)	C7—C6—H6	119.2
N2—Pb1—O2^i	78.37 (12)	C8—C7—C12	117.6 (5)
O1—Pb1—O2^i	111.94 (12)	C8—C7—C6	123.6 (5)
N1—Pb1—O3	84.87 (12)	C12—C7—C6	118.8 (5)
N2—Pb1—O3	82.95 (11)	C9—C8—C7	120.0 (5)
O1—Pb1—O3	73.54 (11)	C9—C8—H8	120.0
O2^i—Pb1—O3	156.80 (12)	C7—C8—H8	120.0
N1—Pb1—O1^i	95.32 (12)	C8—C9—C10	118.2 (5)
N2—Pb1—O1^i	127.26 (11)	C8—C9—H9	120.9
O1—Pb1—O1^i	74.01 (12)	C10—C9—H9	120.9
O2^i—Pb1—O1^i	48.91 (11)	N2—C10—C9	123.9 (5)
O3—Pb1—O1^i	146.69 (10)	N2—C10—H10	118.0
O5—S1—O4	112.8 (3)	C9—C10—H10	118.0
O5—S1—O3	113.1 (3)	N1—C11—C4	122.6 (5)
O4—S1—O3	110.9 (2)	N1—C11—C12	118.9 (4)
O5—S1—C15	106.9 (3)	C4—C11—C12	118.4 (4)
O4—S1—C15	106.3 (2)	N2—C12—C7	121.9 (5)
O3—S1—C15	106.3 (2)	N2—C12—C11	118.2 (4)
C13—O1—Pb1	142.7 (3)	C7—C12—C11	119.9 (4)
C13—O1—Pb1^i	90.1 (3)	O1—C13—O2	123.2 (5)
Pb1—O1—Pb1^i	105.99 (12)	O1—C13—C14	119.4 (4)
S1—O3—Pb1	107.52 (18)	O2—C13—C14	117.2 (4)
C1—N1—C11	117.9 (4)	C19—C14—C15	118.3 (5)
C1—N1—Pb1	122.7 (3)	C19—C14—C13	116.4 (4)
C11—N1—Pb1	119.2 (3)	C15—C14—C13	125.3 (4)
C10—N2—C12	118.4 (4)	C16—C15—C14	119.9 (5)
C10—N2—Pb1	123.3 (3)	C16—C15—S1	117.1 (4)
C12—N2—Pb1	118.1 (3)	C14—C15—S1	123.0 (4)
N1—C1—C2	123.5 (5)	C17—C16—C15	120.9 (5)
N1—C1—H1	118.2	C17—C16—H16	119.6
C2—C1—H1	118.2	C15—C16—H16	119.6
C3—C2—C1	118.9 (5)	C16—C17—C18	120.1 (5)
C3—C2—H2	120.6	C16—C17—H17	120.0
C1—C2—H2	120.6	C18—C17—H17	120.0
C2—C3—C4	119.7 (5)	C17—C18—C19	120.1 (5)
C2—C3—H3	120.1	C17—C18—H18	119.9
C4—C3—H3	120.1	C19—C18—H18	119.9
C11—C4—C3	117.3 (5)	C18—C19—C14	120.6 (5)
C11—C4—C5	120.3 (5)	C18—C19—H19	119.7
C3—C4—C5	122.3 (5)	C14—C19—H19	119.7
C6—C5—C4	121.0 (5)	C13—O2—Pb1^i	96.6 (3)
N1—Pb1—O1—C13	−148.4 (6)	C7—C8—C9—C10	0.2 (9)
N2—Pb1—O1—C13	−119.6 (5)	C12—N2—C10—C9	−1.0 (8)
O2^i—Pb1—O1—C13	143.8 (5)	Pb1—N2—C10—C9	173.5 (4)
O3—Pb1—O1—C13	−60.1 (5)	C8—C9—C10—N2	0.7 (9)
O1^i—Pb1—O1—C13	112.3 (6)	C1—N1—C11—C4	0.5 (7)
N1—Pb1—O1—Pb1^i	99.33 (14)	Pb1—N1—C11—C4	175.0 (4)
N2—Pb1—O1—Pb1^i	128.15 (15)	C1—N1—C11—C12	178.9 (5)
O2^i—Pb1—O1—Pb1^i	31.51 (16)	Pb1—N1—C11—C12	−6.6 (6)
O3—Pb1—O1—Pb1^i	−172.39 (15)	C3—C4—C11—N1	−0.2 (8)
O1^i—Pb1—O1—Pb1^i	0.0	C5—C4—C11—N1	179.5 (5)
O5—S1—O3—Pb1	136.2 (2)	C3—C4—C11—C12	−178.6 (5)
O4—S1—O3—Pb1	8.3 (2)	C5—C4—C11—C12	1.1 (8)
C15—S1—O3—Pb1	−106.9 (2)	C10—N2—C12—C7	0.5 (7)
N1—Pb1—O3—S1	142.3 (2)	Pb1—N2—C12—C7	−174.4 (4)
N2—Pb1—O3—S1	−152.2 (2)	C10—N2—C12—C11	−180.0 (4)
O1—Pb1—O3—S1	63.87 (19)	Pb1—N2—C12—C11	5.2 (6)
O2^i—Pb1—O3—S1	171.3 (2)	C8—C7—C12—N2	0.4 (8)
O1^i—Pb1—O3—S1	50.5 (3)	C6—C7—C12—N2	−179.5 (5)
N2—Pb1—N1—C1	−179.4 (4)	C8—C7—C12—C11	−179.2 (5)
O1—Pb1—N1—C1	−20.6 (4)	C6—C7—C12—C11	0.9 (8)
O2^i—Pb1—N1—C1	96.6 (4)	N1—C11—C12—N2	0.9 (7)
O3—Pb1—N1—C1	−94.8 (4)	C4—C11—C12—N2	179.4 (5)
O1^i—Pb1—N1—C1	51.8 (4)	N1—C11—C12—C7	−179.6 (5)
N2—Pb1—N1—C11	6.4 (3)	C4—C11—C12—C7	−1.1 (7)
O1—Pb1—N1—C11	165.2 (4)	Pb1—O1—C13—O2	−106.1 (6)
O2^i—Pb1—N1—C11	−77.6 (3)	Pb1^i—O1—C13—O2	11.1 (5)
O3—Pb1—N1—C11	91.0 (3)	Pb1—O1—C13—C14	79.0 (7)
O1^i—Pb1—N1—C11	−122.4 (3)	Pb1^i—O1—C13—C14	−163.8 (4)
N1—Pb1—N2—C10	179.6 (4)	O1—C13—C14—C19	125.3 (5)
O1—Pb1—N2—C10	148.3 (4)	O2—C13—C14—C19	−49.9 (6)
O2^i—Pb1—N2—C10	−101.9 (4)	O1—C13—C14—C15	−54.2 (7)
O3—Pb1—N2—C10	92.0 (4)	O2—C13—C14—C15	130.6 (5)
O1^i—Pb1—N2—C10	−103.5 (4)	C19—C14—C15—C16	2.6 (7)
N1—Pb1—N2—C12	−5.9 (3)	C13—C14—C15—C16	−177.8 (5)
O1—Pb1—N2—C12	−37.1 (4)	C19—C14—C15—S1	−178.3 (4)
O2^i—Pb1—N2—C12	72.7 (3)	C13—C14—C15—S1	1.2 (7)
O3—Pb1—N2—C12	−93.5 (3)	O5—S1—C15—C16	19.0 (5)
O1^i—Pb1—N2—C12	71.1 (4)	O4—S1—C15—C16	139.8 (4)
C11—N1—C1—C2	0.1 (8)	O3—S1—C15—C16	−102.0 (4)
Pb1—N1—C1—C2	−174.2 (4)	O5—S1—C15—C14	−160.1 (4)
N1—C1—C2—C3	−1.0 (9)	O4—S1—C15—C14	−39.4 (5)
C1—C2—C3—C4	1.3 (9)	O3—S1—C15—C14	78.9 (4)
C2—C3—C4—C11	−0.7 (8)	C14—C15—C16—C17	−3.7 (8)
C2—C3—C4—C5	179.5 (6)	S1—C15—C16—C17	177.2 (4)
C11—C4—C5—C6	−1.1 (10)	C15—C16—C17—C18	2.4 (9)
C3—C4—C5—C6	178.7 (6)	C16—C17—C18—C19	−0.1 (9)
C4—C5—C6—C7	0.9 (11)	C17—C18—C19—C14	−0.9 (9)
C5—C6—C7—C8	179.3 (7)	C15—C14—C19—C18	−0.4 (8)
C5—C6—C7—C12	−0.9 (10)	C13—C14—C19—C18	−179.9 (5)
C12—C7—C8—C9	−0.7 (9)	O1—C13—O2—Pb1^i	−11.8 (5)
C6—C7—C8—C9	179.2 (6)	C14—C13—O2—Pb1^i	163.3 (4)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O2^i	0.92 (12)	1.88 (12)	2.770 (7)	163 (10)

Symmetry code: (i) −x+2, −y+1, −z+1.