catena-Poly[tetra­kis(3-phenyl­propyl­ammonium) [iodo­plumbate(II)-tri-μ-iodo-plumbate(II)-tri-μ-iodo-iodo­plumbate(II)-di-μ-iodo]]

The title compound, {(C₉H₁₄N)₄[Pb₃I₁₀]}_n, crystallizes as an organic–inorganic hybrid. As such, the structure consists of a two-dimensional inorganic layer of [Pb₃I₁₀]_n⁴ⁿ⁻ ions extending along [100]. The asymmetric unit contains two independent Pb atoms, viz. one in a general position and the other on an inversion centre. Each Pb atom is octa­hedrally coordinated by six iodide ions and exhibits both face- and corner-sharing with adjacent atoms in the inorganic layer. These anionic layers alternate with 3-phenyl­propyl­ammonium cations, which hydrogen bond to the iodides. Simple face-to-edge σ–π stacking inter­actions are observed between the aromatic rings that stabilize the overall three-dimensional structure. This net structure has only been observed five times previously.

S1. Comment

In recent years, a significant number of organic–inorganic hybrid materials based on lead and tin halide units have been prepared and studied. For reviews see Papavassiliou (1997) and Mitzi (1999 or? 2001). Haloplumbates in particular have demonstrated a propensity for forming a great variety of crystalline structures. This diversity is a result of the metal–halide octahedra joining in different combinations of face-, edge- and corner-sharing octahedra. As a result, the MX₆ (X = Br and I, and M = Sn and Pb) octahedra building blocks become severely distorted. One of the possible structural motifs forms two-dimensional layers, where chains of two or three trans face-sharing octahedra are connected via four halides on both ends. This can be summarized by the formula (M_nX_{3n + 1})^{(n + 1)-}. To our knowledge, only one structure with n = 2 has been reported, which has isolated I⁻ anions between the lead iodide layers (Krautscheid et al., 1998).

The case with n = 3 has been observed with both lead bromide in [PhMe₃N]₄[Pb₃Br₁₀] (Wiest et al., 1999) and tin iodide [PhMe₃N]₄[Sn₃I₁₀] (Lode & Krautscheid, 2001). We present here the synthesis and crystal structure of the n = 3 case that has [Pb₃I₁₀]⁴⁻ two-dimensional layers separated by the cation C₆H₅C₃H₆NH₃⁺.

The atomic numbering scheme of (I) is shown in Fig. 1. The building block [Pb₃I₁₀]⁴⁻ has two crystallographically independent Pb atoms, Pb1 and Pb2. Pb2 is the central Pb atom and sits on an inversion centre through which the third Pb atom, Pb1(−x + 3/2, y + 1/2, z), is generated to complete the simplest repeating unit. The three Pb atoms are connected by sharing trans faces made up of µ₂-I bridges, with atoms I3, I4 and I5 and their inversion equivalents related through Pb2. The outer octahedra on either end connect to adjacent [Pb₃I₁₀]⁴⁻ units via I2 µ₂ bridges which are far from linear [Pb1ⁱ—I2—Pb1 = 142.51 (3)°], in contrast to the almost linear bridges found in [Sn₃I₁₀]⁴⁻ with an angle of 169.87 (3)° (Lode & Krautscheid, 2001) (see Fig. 2). The resulting inorganic layer sits in the ab plane and is corrugated as the trimeric units connect in an alternating trans fashion (see Fig. 3) as seen in [C₆H₅NH₃]₄[Cd₃Br₁₀] (Ishihara et al., 1994) and [C₆H₅CH₂SC(NH₂)₂]₄[Pb₃I₁₀] (Raptopoulou et al., 2002). The other two n = 3 structures mentioned above have the individual building blocks cis related.

The Pb atoms show different degrees of distortion. The central Pb2 atom has three almost equal bond lengths to the I atoms with bond lengths of 3.2006 (7)–3.2090 (7) Å. This uniformity is due to the identical face-sharing that occurs with the neighbouring Pb1 atoms. The outer Pb1 octahedra are more distorted, with long Pb—I bond lengths of 3.2288 (8)–3.3381 (9) Å when the I atoms are involved in face-sharing and short bond lengths to the corner-sharing iodide I2 and the terminal non-bridging I1 (see Table 1).

Sandwiched between the inorganic nets are two unique organic aromatic amines, cat1 and cat2. Fig. 3 clearly shows the bidimemsional arrangement of the cations. Both propylammonium groups have an all-trans conformation and deviate by 9.3 (11) and 14.2 (11)° from the normal to the aromatic rings, respectively. The two ammonium groups display the same hydrogen-bonding scheme, viz. one bifurcated and two normal hydrogen bonds. The bifurcated bond distances are similiar for atoms N1 and N2 as they both bond to atoms I4 (2.95 and 2.94 Å) and I2 (3.11 and 3.07 Å). Atom N1 has a long hydrogen bond and a short normal hydrogen bond (2.95 and 2.66 Å) as it bonds to an equatorial (I3) and axial (I5) I atom, respectively. Atom N2, however, has two similiar hydrogen bonds (2.82 and 2.84 Å) as they both bond to the axial atom I1, which is not involved in any bridging (see Fig. 4).

Between the aromatic rings of cat1 and cat2, a face-to-edge σ–π interaction, C14—H14···Cg1(1 − x,1 − y,1 − z), occurs with a distance of 2.920 Å and an angle of 143.00°. This interaction is between two cations that hydrogen bond to adjacent two-dimensional nets and so form a three-dimensional system (see Fig. 3).

S2. Experimental

PbO (0.184 g, 0.824 mmol) and C₆H₅C₃H₆NH₂ (0.167 g, 1.23 mmol) were dissolved in HI (3 ml) and then heated to form a clear solution. Upon slow cooling to room temperature, yellow crystals formed. A single-crystal suitable for X-ray diffraction was selected and mounted on a glass fibre. Analysis calculated for C₃₆H₅₆I₁₀N₄Pb₃: C 17.75, H 2.32, N 2.30%; found: C 18.96, H 2.55, N 2.55%.

S3. Refinement

All H atoms were refined in idealized positions in the riding-model approximation, with their U_iso values fixed to 1.2U_eq of the atom to which they are bonded.

Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-Plus (Bruker, 1999) and SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The asymmetric unit of (I) and some adjacent atoms, showing the atomic numbering scheme. Displacement ellipsoids are shown at the 50% probability level. Atoms labelled with superscript a are at the symmetry position (−x, −y, −z).
	Fig. 2. Fiure 2. An illustration of the [Pb3I10]n^4n− two-dimensional net.
	Fig. 3. Packing diagram of (I) viewed along the b axis. Solid lines show the face-to-edge σ–π interaction between cat1 and cat2 which forms a three-dimensional system.
	Fig. 4. Hydrogen bridging interactions (dashed lines) between the ammonium heads and the halogen atoms of (I).

catena-Poly[tetrakis(3-phenylpropylammonium) [iodoplumbate(II)-tri-µ-iodo-plumbate(II)-tri-µ-iodo- iodoplumbate(II)-di-µ-iodo]]

Crystal data

(C9H14N)4[Pb3I10]	F(000) = 4304
Mr = 2435.42	Dx = 2.74 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 903 reflections
a = 20.777 (3) Å	θ = 4.6–56.5°
b = 8.4689 (11) Å	µ = 13.79 mm^−1
c = 33.550 (5) Å	T = 173 K
V = 5903.3 (14) Å^3	Rectangular block, yellow
Z = 4	0.37 × 0.21 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer	5479 reflections with I > 2σ(I)
ϕ and ω scans	Rint = 0.075
Absorption correction: integration ?	θmax = 28°, θmin = 1.6°
Tmin = 0.073, Tmax = 0.393	h = −27→27
27663 measured reflections	k = −10→11
7120 independent reflections	l = −44→30

Refinement

Refinement on F^2	162 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0228P)^2 + 63.008P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.094	(Δ/σ)max = 0.001
S = 1.14	Δρmax = 1.49 e Å^−3
7120 reflections	Δρmin = −2.10 e Å^−3
217 parameters

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.

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

	x	y	z	Uiso*/Ueq
C1	0.6953 (4)	−0.3247 (11)	−0.14757 (17)	0.037 (2)
C2	0.6425 (4)	−0.2523 (11)	−0.1653 (2)	0.051 (3)
H2	0.6118	−0.1983	−0.1493	0.061*
C3	0.6345 (4)	−0.2588 (13)	−0.2064 (2)	0.066 (4)
H3	0.5985	−0.2092	−0.2185	0.079*
C4	0.6794 (5)	−0.3378 (13)	−0.22978 (17)	0.069 (4)
H4	0.674	−0.3423	−0.2579	0.083*
C5	0.7322 (5)	−0.4103 (12)	−0.2121 (3)	0.069 (4)
H5	0.7628	−0.4643	−0.2281	0.083*
C6	0.7401 (4)	−0.4038 (11)	−0.1710 (3)	0.055 (3)
H6	0.7762	−0.4533	−0.1589	0.066*
C7	0.7014 (6)	−0.3223 (16)	−0.1033 (3)	0.044 (3)
H7A	0.6902	−0.2158	−0.0934	0.053*
H7B	0.7466	−0.3442	−0.0959	0.053*
C8	0.6569 (5)	−0.4463 (13)	−0.0830 (3)	0.028 (2)
H8A	0.6127	−0.4372	−0.0939	0.034*
H8B	0.6729	−0.5541	−0.0888	0.034*
C9	0.6558 (6)	−0.4191 (14)	−0.0386 (3)	0.038 (2)
H9A	0.6465	−0.3066	−0.033	0.045*
H9B	0.6984	−0.445	−0.0271	0.045*
C10	0.5499 (4)	−0.6487 (11)	0.25952 (18)	0.045 (2)
C11	0.5086 (4)	−0.5749 (10)	0.2863 (2)	0.052 (3)
H11	0.4766	−0.5041	0.2768	0.062*
C12	0.5142 (4)	−0.6048 (11)	0.3269 (2)	0.056 (3)
H12	0.4859	−0.5544	0.3452	0.067*
C13	0.5610 (4)	−0.7085 (12)	0.34071 (18)	0.057 (3)
H13	0.5648	−0.7289	0.3685	0.068*
C14	0.6023 (4)	−0.7822 (11)	0.3140 (3)	0.058 (3)
H14	0.6343	−0.853	0.3234	0.069*
C15	0.5967 (4)	−0.7523 (11)	0.2734 (2)	0.052 (3)
H15	0.625	−0.8028	0.2551	0.063*
C16	0.5475 (7)	−0.6088 (17)	0.2156 (4)	0.049 (3)
H16A	0.5063	−0.5548	0.2098	0.058*
H16B	0.5485	−0.708	0.2	0.058*
C17	0.6029 (6)	−0.5036 (17)	0.2021 (3)	0.044 (3)
H17A	0.5992	−0.3993	0.2152	0.053*
H17B	0.6442	−0.5517	0.2103	0.053*
C18	0.6025 (6)	−0.4821 (16)	0.1582 (4)	0.044 (3)
H18A	0.561	−0.435	0.1499	0.053*
H18B	0.6066	−0.5863	0.1451	0.053*
N1	0.6043 (4)	−0.5228 (11)	−0.0198 (3)	0.032 (2)
H1A	0.6038	−0.5067	0.0071	0.048*
H1B	0.6132	−0.626	−0.0249	0.048*
H1C	0.5652	−0.4976	−0.0302	0.048*
N2	0.6565 (5)	−0.3776 (12)	0.1450 (3)	0.040 (2)
H2A	0.6552	−0.3663	0.1181	0.06*
H2B	0.6947	−0.4216	0.1522	0.06*
H2C	0.6524	−0.2812	0.1568	0.06*
I1	0.67125 (4)	0.05002 (10)	0.16238 (2)	0.03461 (18)
I2	0.78375 (3)	−0.11079 (9)	0.06215 (2)	0.02979 (16)
I3	0.51744 (3)	0.25984 (8)	0.06872 (2)	0.02690 (15)
I4	0.55761 (3)	−0.25593 (8)	0.060842 (19)	0.02525 (15)
I5	0.64396 (3)	0.06978 (9)	−0.029021 (18)	0.02584 (15)
Pb1	0.649813 (17)	0.06022 (5)	0.070380 (11)	0.02068 (9)
Pb2	0.5	0	0	0.02125 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.042 (5)	0.032 (6)	0.035 (4)	−0.002 (4)	0.003 (3)	0.012 (4)
C2	0.052 (6)	0.064 (8)	0.036 (4)	0.014 (6)	0.004 (4)	0.016 (6)
C3	0.076 (8)	0.086 (10)	0.036 (5)	0.005 (7)	−0.004 (5)	0.024 (6)
C4	0.107 (10)	0.068 (9)	0.032 (5)	−0.017 (7)	0.012 (5)	0.004 (6)
C5	0.090 (9)	0.055 (9)	0.063 (5)	0.001 (7)	0.035 (6)	−0.007 (7)
C6	0.053 (7)	0.046 (8)	0.065 (5)	0.006 (5)	0.017 (5)	0.009 (6)
C7	0.046 (6)	0.049 (7)	0.037 (4)	−0.024 (5)	−0.008 (4)	0.011 (5)
C8	0.031 (5)	0.022 (5)	0.033 (4)	0.001 (4)	−0.003 (4)	0.007 (4)
C9	0.047 (6)	0.032 (6)	0.035 (4)	−0.009 (5)	−0.004 (5)	0.008 (5)
C10	0.044 (6)	0.041 (6)	0.051 (4)	−0.001 (4)	0.009 (4)	−0.004 (4)
C11	0.050 (7)	0.049 (7)	0.058 (5)	0.014 (5)	0.018 (5)	0.010 (6)
C12	0.052 (7)	0.062 (8)	0.054 (5)	0.007 (5)	0.027 (5)	0.002 (6)
C13	0.055 (7)	0.073 (9)	0.042 (5)	−0.001 (6)	0.014 (5)	0.011 (6)
C14	0.056 (7)	0.057 (8)	0.060 (6)	0.011 (6)	0.008 (5)	0.004 (6)
C15	0.047 (6)	0.055 (8)	0.055 (5)	0.013 (5)	0.014 (5)	−0.003 (6)
C16	0.049 (6)	0.044 (7)	0.053 (5)	0.007 (5)	0.010 (5)	−0.002 (5)
C17	0.051 (6)	0.045 (7)	0.036 (4)	−0.003 (5)	−0.001 (5)	−0.010 (5)
C18	0.047 (6)	0.047 (7)	0.039 (5)	0.001 (5)	−0.004 (5)	−0.004 (5)
N1	0.041 (5)	0.024 (5)	0.032 (4)	−0.004 (4)	0.000 (4)	−0.002 (4)
N2	0.038 (5)	0.042 (6)	0.040 (5)	0.009 (4)	−0.006 (4)	0.003 (4)
I1	0.0384 (4)	0.0438 (5)	0.0216 (3)	0.0010 (4)	0.0053 (3)	0.0004 (3)
I2	0.0265 (3)	0.0268 (4)	0.0361 (4)	0.0106 (3)	0.0042 (3)	0.0005 (3)
I3	0.0206 (3)	0.0248 (4)	0.0353 (3)	0.0036 (3)	−0.0035 (3)	−0.0083 (3)
I4	0.0299 (3)	0.0189 (3)	0.0269 (3)	−0.0001 (3)	−0.0018 (3)	0.0042 (3)
I5	0.0237 (3)	0.0270 (4)	0.0269 (3)	−0.0023 (3)	0.0032 (2)	−0.0009 (3)
Pb1	0.01873 (16)	0.01992 (19)	0.02340 (17)	0.00006 (15)	−0.00114 (14)	0.00033 (16)
Pb2	0.0195 (2)	0.0185 (3)	0.0257 (2)	−0.0013 (2)	−0.0040 (2)	0.0010 (2)

Geometric parameters (Å, º)

C1—C2	1.39	C14—H14	0.95
C1—C6	1.39	C15—H15	0.95
C1—C7	1.490 (13)	C16—C17	1.523 (18)
C2—C3	1.39	C16—H16A	0.99
C2—H2	0.95	C16—H16B	0.99
C3—C4	1.39	C17—C18	1.483 (16)
C3—H3	0.95	C17—H17A	0.99
C4—C5	1.39	C17—H17B	0.99
C4—H4	0.95	C18—N2	1.496 (16)
C5—C6	1.39	C18—H18A	0.99
C5—H5	0.95	C18—H18B	0.99
C6—H6	0.95	N1—H1A	0.91
C7—C8	1.556 (15)	N1—H1B	0.91
C7—H7A	0.99	N1—H1C	0.91
C7—H7B	0.99	N2—H2A	0.91
C8—C9	1.508 (15)	N2—H2B	0.91
C8—H8A	0.99	N2—H2C	0.91
C8—H8B	0.99	I1—Pb1	3.1197 (9)
C9—N1	1.521 (14)	I2—Pb1^i	3.1217 (8)
C9—H9A	0.99	I2—Pb1	3.1492 (8)
C9—H9B	0.99	I3—Pb2	3.2078 (7)
C10—C11	1.39	I3—Pb1	3.2288 (8)
C10—C15	1.39	I4—Pb2	3.2090 (7)
C10—C16	1.513 (14)	I4—Pb1	3.3077 (8)
C11—C12	1.39	I5—Pb2	3.2006 (7)
C11—H11	0.95	I5—Pb1	3.3381 (9)
C12—C13	1.39	Pb1—I2^ii	3.1217 (8)
C12—H12	0.95	Pb2—I5^iii	3.2006 (7)
C13—C14	1.39	Pb2—I3^iii	3.2078 (7)
C13—H13	0.95	Pb2—I4^iii	3.2090 (7)
C14—C15	1.39
C2—C1—C6	120	H16A—C16—H16B	107.7
C2—C1—C7	119.1 (8)	C18—C17—C16	111.3 (11)
C6—C1—C7	120.8 (8)	C18—C17—H17A	109.4
C1—C2—C3	120	C16—C17—H17A	109.4
C1—C2—H2	120	C18—C17—H17B	109.4
C3—C2—H2	120	C16—C17—H17B	109.4
C4—C3—C2	120	H17A—C17—H17B	108
C4—C3—H3	120	C17—C18—N2	111.3 (10)
C2—C3—H3	120	C17—C18—H18A	109.4
C5—C4—C3	120	N2—C18—H18A	109.4
C5—C4—H4	120	C17—C18—H18B	109.4
C3—C4—H4	120	N2—C18—H18B	109.4
C4—C5—C6	120	H18A—C18—H18B	108
C4—C5—H5	120	C9—N1—H1A	109.5
C6—C5—H5	120	C9—N1—H1B	109.5
C5—C6—C1	120	H1A—N1—H1B	109.5
C5—C6—H6	120	C9—N1—H1C	109.5
C1—C6—H6	120	H1A—N1—H1C	109.5
C1—C7—C8	112.1 (9)	H1B—N1—H1C	109.5
C1—C7—H7A	109.2	C18—N2—H2A	109.5
C8—C7—H7A	109.2	C18—N2—H2B	109.5
C1—C7—H7B	109.2	H2A—N2—H2B	109.5
C8—C7—H7B	109.2	C18—N2—H2C	109.5
H7A—C7—H7B	107.9	H2A—N2—H2C	109.5
C9—C8—C7	109.7 (9)	H2B—N2—H2C	109.5
C9—C8—H8A	109.7	Pb1^i—I2—Pb1	142.51 (3)
C7—C8—H8A	109.7	Pb2—I3—Pb1	75.488 (16)
C9—C8—H8B	109.7	Pb2—I4—Pb1	74.385 (17)
C7—C8—H8B	109.7	Pb2—I5—Pb1	74.076 (15)
H8A—C8—H8B	108.2	I1—Pb1—I2^ii	92.82 (2)
C8—C9—N1	109.4 (9)	I1—Pb1—I2	87.01 (2)
C8—C9—H9A	109.8	I2^ii—Pb1—I2	90.685 (15)
N1—C9—H9A	109.8	I1—Pb1—I3	98.81 (2)
C8—C9—H9B	109.8	I2^ii—Pb1—I3	84.71 (2)
N1—C9—H9B	109.8	I2—Pb1—I3	172.73 (2)
H9A—C9—H9B	108.2	I1—Pb1—I4	98.97 (2)
C11—C10—C15	120	I2^ii—Pb1—I4	165.93 (2)
C11—C10—C16	120.6 (7)	I2—Pb1—I4	97.53 (2)
C15—C10—C16	119.3 (7)	I3—Pb1—I4	85.92 (2)
C12—C11—C10	120	I1—Pb1—I5	173.87 (2)
C12—C11—H11	120	I2^ii—Pb1—I5	84.61 (2)
C10—C11—H11	120	I2—Pb1—I5	87.460 (19)
C11—C12—C13	120	I3—Pb1—I5	86.508 (19)
C11—C12—H12	120	I4—Pb1—I5	84.370 (18)
C13—C12—H12	120	I5—Pb2—I5^iii	180.00 (3)
C14—C13—C12	120	I5—Pb2—I3^iii	90.778 (17)
C14—C13—H13	120	I5^iii—Pb2—I3^iii	89.222 (17)
C12—C13—H13	120	I5—Pb2—I3	89.222 (17)
C15—C14—C13	120	I5^iii—Pb2—I3	90.778 (17)
C15—C14—H14	120	I3^iii—Pb2—I3	180.000 (17)
C13—C14—H14	120	I5—Pb2—I4	88.259 (18)
C14—C15—C10	120	I5^iii—Pb2—I4	91.741 (18)
C14—C15—H15	120	I3^iii—Pb2—I4	92.06 (2)
C10—C15—H15	120	I3—Pb2—I4	87.94 (2)
C10—C16—C17	113.3 (11)	I5—Pb2—I4^iii	91.741 (18)
C10—C16—H16A	108.9	I5^iii—Pb2—I4^iii	88.259 (18)
C17—C16—H16A	108.9	I3^iii—Pb2—I4^iii	87.94 (2)
C10—C16—H16B	108.9	I3—Pb2—I4^iii	92.06 (2)
C17—C16—H16B	108.9	I4—Pb2—I4^iii	180.00 (3)
C6—C1—C2—C3	0	Pb2—I3—Pb1—I2^ii	126.658 (19)
C7—C1—C2—C3	−177.4 (9)	Pb2—I3—Pb1—I2	75.76 (18)
C1—C2—C3—C4	0	Pb2—I3—Pb1—I4	−42.838 (16)
C2—C3—C4—C5	0	Pb2—I3—Pb1—I5	41.757 (17)
C3—C4—C5—C6	0	Pb2—I4—Pb1—I1	141.383 (19)
C4—C5—C6—C1	0	Pb2—I4—Pb1—I2^ii	−5.23 (9)
C2—C1—C6—C5	0	Pb2—I4—Pb1—I2	−130.470 (18)
C7—C1—C6—C5	177.3 (9)	Pb2—I4—Pb1—I3	43.095 (16)
C2—C1—C7—C8	78.1 (12)	Pb2—I4—Pb1—I5	−43.791 (16)
C6—C1—C7—C8	−99.3 (11)	Pb2—I5—Pb1—I1	167.4 (2)
C1—C7—C8—C9	−169.8 (10)	Pb2—I5—Pb1—I2^ii	−127.228 (18)
C7—C8—C9—N1	171.0 (9)	Pb2—I5—Pb1—I2	141.84 (2)
C15—C10—C11—C12	0	Pb2—I5—Pb1—I3	−42.219 (18)
C16—C10—C11—C12	−175.7 (10)	Pb2—I5—Pb1—I4	44.019 (16)
C10—C11—C12—C13	0	Pb1—I5—Pb2—I5^iii	−35 (16)
C11—C12—C13—C14	0	Pb1—I5—Pb2—I3^iii	−137.533 (18)
C12—C13—C14—C15	0	Pb1—I5—Pb2—I3	42.467 (18)
C13—C14—C15—C10	0	Pb1—I5—Pb2—I4	−45.492 (17)
C11—C10—C15—C14	0	Pb1—I5—Pb2—I4^iii	134.508 (18)
C16—C10—C15—C14	175.8 (10)	Pb1—I3—Pb2—I5	−43.897 (18)
C11—C10—C16—C17	104.2 (11)	Pb1—I3—Pb2—I5^iii	136.103 (18)
C15—C10—C16—C17	−71.5 (12)	Pb1—I3—Pb2—I3^iii	0.00 (4)
C10—C16—C17—C18	173.8 (11)	Pb1—I3—Pb2—I4	44.389 (17)
C16—C17—C18—N2	179.4 (10)	Pb1—I3—Pb2—I4^iii	−135.611 (17)
Pb1^i—I2—Pb1—I1	77.26 (5)	Pb1—I4—Pb2—I5	45.940 (17)
Pb1^i—I2—Pb1—I2^ii	170.04 (3)	Pb1—I4—Pb2—I5^iii	−134.060 (17)
Pb1^i—I2—Pb1—I3	−139.36 (15)	Pb1—I4—Pb2—I3^iii	136.656 (16)
Pb1^i—I2—Pb1—I4	−21.41 (5)	Pb1—I4—Pb2—I3	−43.344 (16)
Pb1^i—I2—Pb1—I5	−105.39 (4)	Pb1—I4—Pb2—I4^iii	111.137 (12)
Pb2—I3—Pb1—I1	−141.30 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···I4	0.91	2.95	3.655 (9)	136
N1—H1A···I2^i	0.91	3.11	3.676 (9)	122
N1—H1B···I5^iv	0.91	2.66	3.561 (9)	172
N1—H1C···I3^iii	0.91	2.95	3.750 (10)	148
N2—H2A···I4	0.91	2.94	3.641 (9)	135
N2—H2A···I2^i	0.91	3.07	3.629 (10)	122
N2—H2B···I1^i	0.91	2.82	3.677 (9)	159
N2—H2C···I1	0.91	2.84	3.680 (11)	155

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