Poly[[bis­(μ-1,2-bis­{[2-(2-pyrid­yl)-1H-imidazol-1-yl]meth­yl}benzene)lead(II)] dithio­cyanate]

The title Pb^II coordination polymer, {[Pb(C₂₄H₂₀N₆)₂](SCN)₂}_n, was obtained by the reaction of Pb(CH₃COO)₂·3H₂O, KSCN and 1,2-bis­{[2-(2-pyrid­yl)-1H-imidazol-1-yl]meth­yl}benzene (hereafter L). Each L mol­ecule coordinates to two Pb^II cations through the four aromatic N atoms, thus acting as a bridging bis-bidentate ligand. The Pb^II cations, which lie on inversion centres, are bridged by four L mol­ecules, forming a two-dimensional (4,4)-sheet. The SCN⁻ anions act as counter-ions and are uncoordinated.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.034
• wR factor = 0.080
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C25

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Pb1         (2)       1.98

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

In recent years, research into coordination polymers has been expanding rapidly because of their fascinating structural diversity and potential application as functional materials (Batten & Robson, 1998; Moulton & Zaworotko, 2001). As a heavy p-block metal ion, lead(II), with its large radius, flexible coordination environment, and variable stereochemical activity, provides unique opportunities for formation of unusual network topologies with interesting properties (Jack et al., 2004). In the present paper, we report the preparation and crystal structure of a novel two-dimensional coordination polymer, namely [Pb(C₂₄H₂₀N₆)₂](SCN)₂, (I).

As shown in Fig. 1, the Pb^II cation occupies the inversion centre and is eight-coordinated by eight N atoms from four L molecules. The average Pb—N distances are 2.689 (4), 2.717 (3), 2.750 (3) and 2.805 (3) Å, respectively, which are in the normal Pb—N range (Carcelli et al., 2003). As illustrated in Fig. 2, each L molecule in (I) coordinates to two Pb^II cations through its four aromatic N atoms, thus acting as a bridging bis(bidentate) ligand. The Pb^II cations, which lie on the inversion centres, are bridged by four L molecules to form a two-dimensional neutral (4,4)-network (Fig. 3). The (SCN)^- anions act as counterions.

Related literature

For related literature, see: Batten & Robson, (1998); Moulton & Zaworotko, (2001); Jack et al., (2004); Carcelli et al. (2003).

S2. Experimental

A mixture of Pb(CH₃COO)₂.3H₂O (0.121 g, 0.5 mmol), KSCN(0.097 g, 1 mmol) and L (0.392 g, 1 mmol) in H₂O (13 ml) was stirred for 0.5 h. The mixture was then transferred and sealed into an 18 ml Teflon-lined autoclave, which was heated at 150 °C for 60 h. After the mixture was cooled to room temperature, colorless blocks of the title complex were filtered off and dried at ambient temperature in air (yield 62% based on Pb).

S3. Refinement

All H atoms on C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 - 0.97 Å, and U_iso=1.2U_eq (C).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. A view of the molecule of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms are omitted for clarity.
	Fig. 2. Ball-stick representation of the two-dimensional structure of (I). All (SCN)^- anions are omitted for clarity.
	Fig. 3. View of the (4,4) sheet.

poly[[bis(µ-1,2-bis{[2-(2-pyridyl)-1H-imidazol-1-yl]methyl}benzene)lead(II)] dithiocyanate]

Crystal data

[Pb(C24H20N6)2](SCN)2	F(000) = 2208
Mr = 1108.27	Dx = 1.646 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9825 reflections
a = 23.9560 (8) Å	θ = 1.9–28.4°
b = 12.6670 (8) Å	µ = 3.92 mm^−1
c = 18.3560 (9) Å	T = 293 K
β = 126.593 (1)°	Block, colorless
V = 4472.2 (4) Å^3	0.36 × 0.31 × 0.28 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer	5253 independent reflections
Radiation source: fine-focus sealed tube	4435 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scans	θmax = 28.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −31→25
Tmin = 0.271, Tmax = 0.333	k = −16→16
13428 measured reflections	l = −24→23

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0448P)^2] where P = (Fo^2 + 2Fc^2)/3
5253 reflections	(Δ/σ)max = 0.001
303 parameters	Δρmax = 1.02 e Å^−3
0 restraints	Δρmin = −1.15 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
Pb1	0.0000	0.369453 (14)	0.7500	0.03277 (8)
S1	0.23584 (15)	0.88594 (17)	0.80144 (19)	0.1210 (8)
C1	0.1039 (3)	0.6026 (3)	0.8718 (3)	0.0527 (11)
H1	0.0700	0.6391	0.8713	0.063*
C2	0.1559 (3)	0.6481 (3)	0.8750 (3)	0.0510 (11)
H2	0.1647	0.7200	0.8774	0.061*
C3	0.1634 (2)	0.4757 (3)	0.8719 (3)	0.0370 (8)
C4	0.1862 (2)	0.3677 (3)	0.8724 (2)	0.0363 (8)
C5	0.2552 (3)	0.3402 (4)	0.9119 (3)	0.0494 (10)
H5	0.2895	0.3919	0.9379	0.059*
C6	0.2721 (3)	0.2370 (4)	0.9124 (4)	0.0581 (12)
H6	0.3179	0.2178	0.9387	0.070*
C7	0.2206 (3)	0.1624 (4)	0.8734 (3)	0.0555 (12)
H7	0.2305	0.0917	0.8722	0.067*
C8	0.1535 (3)	0.1949 (3)	0.8360 (3)	0.0484 (11)
H8	0.1187	0.1439	0.8102	0.058*
C9	0.2509 (2)	0.5851 (3)	0.8679 (3)	0.0401 (9)
H9A	0.2405	0.6467	0.8304	0.048*
H9B	0.2546	0.5250	0.8383	0.048*
C10	0.3202 (2)	0.6016 (3)	0.9593 (3)	0.0338 (8)
C11	0.3293 (2)	0.5842 (3)	1.0405 (3)	0.0417 (9)
H11	0.2916	0.5629	1.0392	0.050*
C12	0.3925 (3)	0.5976 (3)	1.1220 (3)	0.0473 (10)
H12	0.3977	0.5846	1.1756	0.057*
C13	0.4494 (2)	0.6307 (3)	1.1254 (3)	0.0461 (10)
H13	0.4925	0.6400	1.1810	0.055*
C14	0.4414 (2)	0.6498 (3)	1.0452 (3)	0.0418 (9)
H14	0.4794	0.6719	1.0473	0.050*
C15	0.3770 (2)	0.6362 (3)	0.9617 (2)	0.0344 (8)
C16	0.3669 (2)	0.6580 (3)	0.8735 (3)	0.0406 (9)
H16A	0.3425	0.5989	0.8327	0.049*
H16B	0.3378	0.7200	0.8454	0.049*
C17	0.4706 (3)	0.5944 (4)	0.8856 (3)	0.0531 (12)
H17	0.4635	0.5224	0.8868	0.064*
C18	0.5209 (3)	0.6404 (3)	0.8849 (4)	0.0606 (13)
H18	0.5551	0.6042	0.8858	0.073*
C19	0.4607 (2)	0.7666 (3)	0.8829 (3)	0.0397 (9)
C20	0.4387 (2)	0.8735 (3)	0.8845 (3)	0.0387 (8)
C21	0.4112 (3)	0.9009 (4)	0.9309 (3)	0.0506 (11)
H21	0.4033	0.8496	0.9600	0.061*
C22	0.3959 (3)	1.0061 (4)	0.9329 (3)	0.0568 (12)
H22	0.3772	1.0259	0.9630	0.068*
C23	0.4085 (3)	1.0805 (4)	0.8903 (3)	0.0552 (12)
H23	0.3990	1.1514	0.8913	0.066*
C24	0.4356 (3)	1.0471 (3)	0.8456 (3)	0.0479 (10)
H24	0.4434	1.0977	0.8159	0.057*
C25	0.1601 (5)	0.8640 (6)	0.7079 (9)	0.110 (4)
N1	0.4318 (2)	0.6750 (3)	0.8843 (2)	0.0411 (8)
N2	0.5148 (2)	0.7480 (3)	0.8825 (3)	0.0525 (10)
N3	0.45138 (19)	0.9469 (3)	0.8425 (2)	0.0406 (8)
N4	0.1078 (2)	0.4945 (3)	0.8693 (2)	0.0453 (8)
N5	0.19362 (19)	0.5672 (3)	0.8739 (2)	0.0397 (8)
N6	0.13584 (19)	0.2947 (2)	0.8348 (2)	0.0395 (7)
N8	0.1191 (6)	0.8507 (9)	0.6599 (9)	0.182 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pb1	0.03127 (11)	0.03239 (11)	0.04649 (12)	0.000	0.02959 (9)	0.000
S1	0.1069 (18)	0.1023 (15)	0.1358 (19)	0.0092 (13)	0.0626 (16)	−0.0211 (12)
C1	0.052 (3)	0.048 (2)	0.077 (3)	0.000 (2)	0.049 (3)	−0.013 (2)
C2	0.053 (3)	0.038 (2)	0.071 (3)	−0.007 (2)	0.042 (3)	−0.013 (2)
C3	0.032 (2)	0.040 (2)	0.045 (2)	−0.0058 (17)	0.0253 (19)	−0.0043 (16)
C4	0.034 (2)	0.041 (2)	0.0406 (18)	0.0007 (19)	0.0257 (16)	0.0017 (16)
C5	0.038 (2)	0.049 (2)	0.065 (3)	−0.001 (2)	0.033 (2)	−0.001 (2)
C6	0.050 (3)	0.054 (3)	0.083 (3)	0.012 (2)	0.046 (3)	0.005 (2)
C7	0.067 (4)	0.043 (2)	0.069 (3)	0.011 (2)	0.047 (3)	0.008 (2)
C8	0.053 (3)	0.042 (2)	0.054 (2)	−0.003 (2)	0.033 (2)	0.0029 (19)
C9	0.038 (2)	0.044 (2)	0.049 (2)	−0.0081 (19)	0.031 (2)	−0.0035 (17)
C10	0.035 (2)	0.0303 (17)	0.0433 (19)	−0.0031 (16)	0.0271 (18)	−0.0027 (15)
C11	0.047 (3)	0.041 (2)	0.049 (2)	−0.0044 (19)	0.035 (2)	−0.0011 (17)
C12	0.057 (3)	0.048 (2)	0.045 (2)	0.005 (2)	0.034 (2)	0.0059 (18)
C13	0.040 (2)	0.052 (2)	0.0383 (19)	0.005 (2)	0.0193 (18)	0.0019 (18)
C14	0.035 (2)	0.042 (2)	0.051 (2)	0.0019 (18)	0.0268 (19)	0.0051 (17)
C15	0.035 (2)	0.0308 (17)	0.0435 (18)	−0.0022 (17)	0.0267 (17)	0.0016 (16)
C16	0.034 (2)	0.048 (2)	0.048 (2)	−0.0022 (18)	0.0284 (19)	0.0052 (17)
C17	0.061 (3)	0.040 (2)	0.079 (3)	0.011 (2)	0.053 (3)	0.016 (2)
C18	0.065 (3)	0.051 (3)	0.096 (4)	0.025 (3)	0.064 (3)	0.024 (2)
C19	0.041 (2)	0.042 (2)	0.051 (2)	0.0016 (18)	0.035 (2)	0.0061 (17)
C20	0.035 (2)	0.046 (2)	0.0424 (19)	0.0030 (19)	0.0273 (17)	0.0031 (17)
C21	0.057 (3)	0.056 (2)	0.060 (3)	0.002 (2)	0.046 (3)	0.003 (2)
C22	0.065 (3)	0.060 (3)	0.071 (3)	0.006 (3)	0.054 (3)	−0.004 (2)
C23	0.061 (3)	0.047 (2)	0.071 (3)	0.002 (2)	0.047 (3)	−0.008 (2)
C24	0.053 (3)	0.043 (2)	0.053 (2)	−0.002 (2)	0.035 (2)	0.0021 (19)
C25	0.094 (6)	0.050 (3)	0.237 (13)	−0.030 (5)	0.125 (8)	−0.057 (6)
N1	0.042 (2)	0.0398 (17)	0.055 (2)	0.0041 (16)	0.0366 (18)	0.0092 (15)
N2	0.053 (3)	0.049 (2)	0.081 (3)	0.0086 (18)	0.054 (2)	0.0153 (18)
N3	0.042 (2)	0.0425 (18)	0.0474 (19)	−0.0031 (16)	0.0318 (17)	−0.0024 (14)
N4	0.044 (2)	0.0426 (18)	0.067 (2)	−0.0085 (16)	0.043 (2)	−0.0125 (16)
N5	0.0315 (19)	0.0409 (18)	0.0497 (19)	−0.0052 (15)	0.0260 (16)	−0.0044 (14)
N6	0.036 (2)	0.0380 (17)	0.0478 (19)	−0.0002 (15)	0.0269 (17)	0.0018 (14)
N8	0.120 (9)	0.134 (8)	0.213 (12)	0.052 (7)	0.057 (8)	−0.044 (7)

Geometric parameters (Å, º)

Pb1—N4	2.689 (4)	C11—C12	1.364 (7)
Pb1—N4^i	2.689 (4)	C11—H11	0.9300
Pb1—N2^ii	2.717 (3)	C12—C13	1.392 (7)
Pb1—N2^iii	2.717 (3)	C12—H12	0.9300
Pb1—N3^iii	2.750 (3)	C13—C14	1.387 (6)
Pb1—N3^ii	2.750 (3)	C13—H13	0.9300
Pb1—N6	2.805 (3)	C14—C15	1.394 (6)
Pb1—N6^i	2.805 (3)	C14—H14	0.9300
S1—C25	1.614 (12)	C15—C16	1.512 (5)
C1—C2	1.343 (7)	C16—N1	1.462 (5)
C1—N4	1.376 (5)	C16—H16A	0.9700
C1—H1	0.9300	C16—H16B	0.9700
C2—N5	1.373 (6)	C17—C18	1.347 (7)
C2—H2	0.9300	C17—N1	1.371 (6)
C3—N4	1.326 (5)	C17—H17	0.9300
C3—N5	1.355 (5)	C18—N2	1.368 (5)
C3—C4	1.472 (5)	C18—H18	0.9300
C4—N6	1.341 (5)	C19—N2	1.322 (5)
C4—C5	1.395 (6)	C19—N1	1.359 (5)
C5—C6	1.367 (6)	C19—C20	1.460 (5)
C5—H5	0.9300	C20—N3	1.352 (5)
C6—C7	1.370 (7)	C20—C21	1.396 (5)
C6—H6	0.9300	C21—C22	1.387 (6)
C7—C8	1.382 (7)	C21—H21	0.9300
C7—H7	0.9300	C22—C23	1.368 (7)
C8—N6	1.329 (5)	C22—H22	0.9300
C8—H8	0.9300	C23—C24	1.381 (6)
C9—N5	1.458 (5)	C23—H23	0.9300
C9—C10	1.515 (6)	C24—N3	1.336 (5)
C9—H9A	0.9700	C24—H24	0.9300
C9—H9B	0.9700	C25—N8	0.858 (13)
C10—C11	1.389 (5)	N2—Pb1^iv	2.717 (3)
C10—C15	1.405 (5)	N3—Pb1^iv	2.750 (3)
N4—Pb1—N4^i	107.83 (16)	C14—C13—H13	120.2
N4—Pb1—N2^ii	127.73 (11)	C12—C13—H13	120.2
N4^i—Pb1—N2^ii	93.16 (12)	C13—C14—C15	120.5 (4)
N4—Pb1—N2^iii	93.16 (12)	C13—C14—H14	119.8
N4^i—Pb1—N2^iii	127.73 (11)	C15—C14—H14	119.8
N2^ii—Pb1—N2^iii	111.02 (16)	C14—C15—C10	119.3 (3)
N4—Pb1—N3^iii	80.90 (10)	C14—C15—C16	121.4 (4)
N4^i—Pb1—N3^iii	74.82 (10)	C10—C15—C16	119.3 (3)
N2^ii—Pb1—N3^iii	151.37 (12)	N1—C16—C15	113.7 (3)
N2^iii—Pb1—N3^iii	61.71 (10)	N1—C16—H16A	108.8
N4—Pb1—N3^ii	74.82 (10)	C15—C16—H16A	108.8
N4^i—Pb1—N3^ii	80.90 (10)	N1—C16—H16B	108.8
N2^ii—Pb1—N3^ii	61.71 (10)	C15—C16—H16B	108.8
N2^iii—Pb1—N3^ii	151.37 (12)	H16A—C16—H16B	107.7
N3^iii—Pb1—N3^ii	138.22 (14)	C18—C17—N1	106.2 (4)
C2—C1—N4	110.4 (4)	C18—C17—H17	126.9
C2—C1—H1	124.8	N1—C17—H17	126.9
N4—C1—H1	124.8	C17—C18—N2	110.6 (4)
C1—C2—N5	106.3 (4)	C17—C18—H18	124.7
C1—C2—H2	126.8	N2—C18—H18	124.7
N5—C2—H2	126.8	N2—C19—N1	111.1 (4)
N4—C3—N5	110.9 (3)	N2—C19—C20	122.1 (4)
N4—C3—C4	121.9 (3)	N1—C19—C20	126.8 (4)
N5—C3—C4	127.2 (4)	N3—C20—C21	121.7 (4)
N6—C4—C5	121.3 (4)	N3—C20—C19	114.9 (3)
N6—C4—C3	114.9 (4)	C21—C20—C19	123.3 (4)
C5—C4—C3	123.8 (4)	C22—C21—C20	118.8 (4)
C6—C5—C4	119.8 (5)	C22—C21—H21	120.6
C6—C5—H5	120.1	C20—C21—H21	120.6
C4—C5—H5	120.1	C23—C22—C21	119.7 (4)
C5—C6—C7	119.0 (5)	C23—C22—H22	120.2
C5—C6—H6	120.5	C21—C22—H22	120.2
C7—C6—H6	120.5	C22—C23—C24	118.1 (4)
C6—C7—C8	118.3 (4)	C22—C23—H23	121.0
C6—C7—H7	120.9	C24—C23—H23	121.0
C8—C7—H7	120.9	N3—C24—C23	124.1 (4)
N6—C8—C7	123.8 (5)	N3—C24—H24	117.9
N6—C8—H8	118.1	C23—C24—H24	117.9
C7—C8—H8	118.1	N8—C25—S1	177 (2)
N5—C9—C10	113.4 (3)	C19—N1—C17	106.8 (4)
N5—C9—H9A	108.9	C19—N1—C16	129.5 (4)
C10—C9—H9A	108.9	C17—N1—C16	123.2 (4)
N5—C9—H9B	108.9	C19—N2—C18	105.3 (4)
C10—C9—H9B	108.9	C19—N2—Pb1^iv	107.4 (3)
H9A—C9—H9B	107.7	C18—N2—Pb1^iv	123.1 (3)
C11—C10—C15	119.2 (4)	C24—N3—C20	117.6 (3)
C11—C10—C9	122.3 (4)	C24—N3—Pb1^iv	126.9 (3)
C15—C10—C9	118.6 (3)	C20—N3—Pb1^iv	115.4 (2)
C12—C11—C10	121.2 (4)	C3—N4—C1	105.3 (4)
C12—C11—H11	119.4	C3—N4—Pb1	112.4 (2)
C10—C11—H11	119.4	C1—N4—Pb1	124.2 (3)
C11—C12—C13	120.3 (4)	C3—N5—C2	107.0 (4)
C11—C12—H12	119.9	C3—N5—C9	130.0 (3)
C13—C12—H12	119.9	C2—N5—C9	122.8 (3)
C14—C13—C12	119.6 (4)	C8—N6—C4	117.9 (4)
N4—C1—C2—N5	0.4 (6)	C15—C16—N1—C19	−103.2 (5)
N4—C3—C4—N6	25.5 (5)	C15—C16—N1—C17	86.3 (5)
N5—C3—C4—N6	−154.5 (4)	N1—C19—N2—C18	−0.7 (5)
N4—C3—C4—C5	−151.8 (4)	C20—C19—N2—C18	177.5 (4)
N5—C3—C4—C5	28.2 (6)	N1—C19—N2—Pb1^iv	132.1 (3)
N6—C4—C5—C6	0.3 (6)	C20—C19—N2—Pb1^iv	−49.7 (5)
C3—C4—C5—C6	177.5 (4)	C17—C18—N2—C19	0.7 (6)
C4—C5—C6—C7	0.2 (7)	C17—C18—N2—Pb1^iv	−122.6 (4)
C5—C6—C7—C8	−0.6 (7)	C23—C24—N3—C20	1.2 (7)
C6—C7—C8—N6	0.7 (7)	C23—C24—N3—Pb1^iv	177.0 (4)
N5—C9—C10—C11	9.7 (6)	C21—C20—N3—C24	−1.1 (6)
N5—C9—C10—C15	−170.0 (3)	C19—C20—N3—C24	−176.8 (4)
C15—C10—C11—C12	−1.6 (6)	C21—C20—N3—Pb1^iv	−177.4 (3)
C9—C10—C11—C12	178.7 (4)	C19—C20—N3—Pb1^iv	6.9 (5)
C10—C11—C12—C13	0.9 (7)	N5—C3—N4—C1	−1.4 (5)
C11—C12—C13—C14	−0.1 (6)	C4—C3—N4—C1	178.6 (4)
C12—C13—C14—C15	0.1 (6)	N5—C3—N4—Pb1	136.6 (3)
C13—C14—C15—C10	−0.7 (6)	C4—C3—N4—Pb1	−43.4 (4)
C13—C14—C15—C16	179.2 (4)	C2—C1—N4—C3	0.6 (5)
C11—C10—C15—C14	1.5 (6)	C2—C1—N4—Pb1	−131.0 (4)
C9—C10—C15—C14	−178.8 (4)	N4^i—Pb1—N4—C3	−122.7 (3)
C11—C10—C15—C16	−178.4 (3)	N2^ii—Pb1—N4—C3	−13.9 (3)
C9—C10—C15—C16	1.3 (5)	N2^iii—Pb1—N4—C3	105.9 (3)
C14—C15—C16—N1	10.4 (5)	N3^iii—Pb1—N4—C3	166.6 (3)
C10—C15—C16—N1	−169.7 (3)	N3^ii—Pb1—N4—C3	−47.7 (3)
N1—C17—C18—N2	−0.4 (6)	N4^i—Pb1—N4—C1	6.1 (3)
N2—C19—C20—N3	31.1 (6)	N2^ii—Pb1—N4—C1	114.9 (3)
N1—C19—C20—N3	−151.0 (4)	N2^iii—Pb1—N4—C1	−125.3 (3)
N2—C19—C20—C21	−144.5 (5)	N3^iii—Pb1—N4—C1	−64.7 (3)
N1—C19—C20—C21	33.4 (7)	N3^ii—Pb1—N4—C1	81.0 (3)
N3—C20—C21—C22	0.8 (7)	N4—C3—N5—C2	1.6 (5)
C19—C20—C21—C22	176.1 (5)	C4—C3—N5—C2	−178.4 (4)
C20—C21—C22—C23	−0.5 (8)	N4—C3—N5—C9	−173.1 (4)
C21—C22—C23—C24	0.6 (8)	C4—C3—N5—C9	6.9 (7)
C22—C23—C24—N3	−1.0 (8)	C1—C2—N5—C3	−1.2 (5)
N2—C19—N1—C17	0.5 (5)	C1—C2—N5—C9	174.0 (4)
C20—C19—N1—C17	−177.6 (4)	C10—C9—N5—C3	−98.8 (5)
N2—C19—N1—C16	−171.2 (4)	C10—C9—N5—C2	87.2 (5)
C20—C19—N1—C16	10.7 (7)	C7—C8—N6—C4	−0.2 (6)
C18—C17—N1—C19	0.0 (5)	C5—C4—N6—C8	−0.3 (5)
C18—C17—N1—C16	172.3 (4)	C3—C4—N6—C8	−177.6 (3)

Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) x−1/2, y−1/2, z; (iv) x+1/2, y+1/2, z.