5,10,15,20-Tetra-kis(1-methyl-pyridinium-4-yl)porphyrin tetra-iodide tetra-hydrate.

The asymmetric unit of the title compound, C(44)H(38)N(8) (2+)·4I(-)·4H(2)O, comprises two halves of non-equivalent cations of 5,10,15,20-tetra-kis-(1-methyl-pyridinium)porphyrin (with the full mol-ecule of each completed by the application of inversion symmetry), four charge balancing iodide anions and four water mol-ecules of crystallization (two water mol-ecules are fully occupied and four mol-ecules have a site occupancy of 50%). The porphyrin cations are arranged into supramolecular columns parallel to the b axis, mediated by π-π [centroid-centroid distance = 3.762 (4) Å] and C-H⋯π supra-molecular inter-actions [C⋯centroid distance = 3.522 (7) Å, C-H⋯centroid = 128°], leading to the formation of columns parallel to the b axis. The close packing leads to the presence of a one-dimensional channel filled with partially occupied water mol-ecules engaged in O-H⋯O and O-H⋯I hydrogen bonds.

Related literature

For general background on the search for alternative treatments for microbial infections, see: Gomes et al. (2011 ▶); Alves et al. (2008 ▶); Carvalho et al. (2009 ▶). For the use of porphyrins as photosensitizers, see: Alves et al. (2009 ▶); Banfi et al. (2006 ▶); Merchat et al. (1996 ▶); Tomé et al. (2004 ▶); Yu et al. (2009 ▶). For general background on the work carried out by our group, see: Paz et al. (2002 ▶); Paz & Klinowski (2003 ▶); Shi et al. (2008 ▶).

Experimental

Crystal data

C44H38N8 2+·4I−·4H2O

M = 1258.49

Monoclinic,

a = 24.3331 (4) Å

b = 6.5209 (1) Å

c = 30.5663 (5) Å

β = 95.025 (1)°

V = 4831.43 (13) Å3

Z = 4

Cu Kα radiation

μ = 20.65 mm−1

T = 100 K

0.20 × 0.15 × 0.08 mm

Data collection

Bruker X8 KappaCCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.104, T max = 0.289

47661 measured reflections

7346 independent reflections

7013 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.110

S = 1.09

7346 reflections

563 parameters

6 restraints

H-atom parameters constrained

Δρmax = 2.73 e Å−3

Δρmin = −2.79 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043844/tk5003sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043844/tk5003Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C44H38N82+·4I−·4H2O	F(000) = 2440
Mr = 1258.49	Dx = 1.730 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 8573 reflections
a = 24.3331 (4) Å	θ = 3.7–62.2°
b = 6.5209 (1) Å	µ = 20.65 mm−1
c = 30.5663 (5) Å	T = 100 K
β = 95.025 (1)°	Block, brown
V = 4831.43 (13) Å3	0.20 × 0.15 × 0.08 mm
Z = 4

Bruker X8 KappaCCD APEXII diffractometer	7346 independent reflections
Radiation source: fine-focus sealed tube	7013 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω and φ scans	θmax = 62.7°, θmin = 7.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −27→27
Tmin = 0.104, Tmax = 0.289	k = −7→7
47661 measured reflections	l = −22→34

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0481P)2 + 42.1978P] where P = (Fo2 + 2Fc2)/3
7346 reflections	(Δ/σ)max = 0.001
563 parameters	Δρmax = 2.73 e Å−3
6 restraints	Δρmin = −2.79 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.46552 (19)	0.1385 (8)	0.05010 (16)	0.0156 (11)
N2	0.43689 (19)	−0.2216 (8)	−0.00352 (16)	0.0161 (11)
H2	0.4640	−0.1320	−0.0009	0.019*
N3	0.24687 (19)	−0.1678 (8)	0.12933 (15)	0.0145 (11)
N4	0.6006 (2)	0.7920 (9)	0.17192 (18)	0.0247 (12)
C1	0.4873 (2)	0.2957 (9)	0.0757 (2)	0.0160 (13)
C2	0.4553 (2)	0.3298 (10)	0.1131 (2)	0.0178 (13)
H2A	0.4630	0.4267	0.1360	0.021*
C3	0.4128 (2)	0.1972 (10)	0.1089 (2)	0.0172 (13)
H3	0.3839	0.1849	0.1278	0.021*
C4	0.4196 (2)	0.0765 (9)	0.06957 (19)	0.0146 (12)
C5	0.3859 (2)	−0.0908 (9)	0.05650 (19)	0.0137 (12)
C6	0.3943 (2)	−0.2300 (9)	0.02283 (19)	0.0153 (13)
C7	0.3613 (2)	−0.4026 (10)	0.0091 (2)	0.0173 (13)
H7	0.3295	−0.4488	0.0222	0.021*
C8	0.3828 (2)	−0.4894 (10)	−0.0258 (2)	0.0192 (14)
H8	0.3687	−0.6060	−0.0417	0.023*
C9	0.4311 (2)	−0.3731 (9)	−0.0346 (2)	0.0174 (13)
C10	0.5360 (2)	0.4044 (9)	0.0686 (2)	0.0161 (13)
C11	0.3363 (2)	−0.1240 (9)	0.08095 (19)	0.0133 (12)
C12	0.2939 (2)	0.0224 (9)	0.07885 (19)	0.0139 (12)
H12	0.2955	0.1386	0.0603	0.017*
C13	0.2500 (2)	−0.0028 (9)	0.1039 (2)	0.0171 (13)
H13	0.2217	0.0980	0.1030	0.021*
C14	0.2850 (2)	−0.3158 (9)	0.13028 (19)	0.0155 (12)
H14	0.2808	−0.4357	0.1473	0.019*
C15	0.3306 (2)	−0.2950 (9)	0.10647 (19)	0.0165 (13)
H15	0.3579	−0.3992	0.1078	0.020*
C16	0.1992 (2)	−0.1914 (10)	0.1559 (2)	0.0211 (14)
H16A	0.1680	−0.2503	0.1376	0.032*
H16B	0.1888	−0.0569	0.1668	0.032*
H16C	0.2093	−0.2825	0.1808	0.032*
C17	0.5575 (2)	0.5474 (9)	0.1041 (2)	0.0155 (12)
C18	0.6056 (2)	0.4934 (10)	0.1296 (2)	0.0201 (14)
H18	0.6243	0.3703	0.1234	0.024*
C19	0.6261 (3)	0.6164 (10)	0.1634 (2)	0.0229 (14)
H19	0.6585	0.5771	0.1809	0.027*
C20	0.5550 (3)	0.8516 (10)	0.1477 (2)	0.0249 (15)
H20	0.5381	0.9781	0.1540	0.030*
C21	0.5323 (3)	0.7323 (10)	0.1136 (2)	0.0212 (14)
H21	0.4996	0.7753	0.0968	0.025*
C22	0.6256 (3)	0.9247 (14)	0.2076 (3)	0.045 (2)
H22A	0.6552	1.0066	0.1967	0.068*
H22B	0.6407	0.8391	0.2322	0.068*
H22C	0.5973	1.0162	0.2177	0.068*
N5	0.51171 (18)	0.1474 (7)	0.44291 (15)	0.0119 (10)
N6	0.54933 (18)	0.2175 (7)	0.53522 (15)	0.0120 (10)
H6	0.5312	0.1189	0.5205	0.014*
N7	0.6882 (2)	0.8716 (8)	0.43573 (17)	0.0179 (11)
N8	0.4068 (2)	−0.1873 (8)	0.25635 (16)	0.0205 (12)
C23	0.4912 (2)	0.0947 (9)	0.40114 (18)	0.0139 (12)
C24	0.5102 (3)	0.2350 (10)	0.3689 (2)	0.0201 (14)
H24	0.5004	0.2334	0.3381	0.024*
C25	0.5444 (3)	0.3681 (9)	0.3913 (2)	0.0182 (13)
H25	0.5647	0.4756	0.3793	0.022*
C26	0.5441 (2)	0.3150 (9)	0.43721 (19)	0.0126 (12)
C27	0.5742 (2)	0.4198 (9)	0.47193 (19)	0.0130 (12)
C28	0.5731 (2)	0.3828 (9)	0.51656 (19)	0.0115 (12)
C29	0.5950 (2)	0.5102 (9)	0.5519 (2)	0.0145 (13)
H29	0.6135	0.6372	0.5490	0.017*
C30	0.5850 (2)	0.4185 (9)	0.59024 (19)	0.0138 (12)
H30	0.5943	0.4717	0.6189	0.017*
C31	0.5579 (2)	0.2279 (9)	0.57998 (19)	0.0138 (12)
C32	0.4584 (2)	−0.0811 (9)	0.39060 (19)	0.0131 (12)
C33	0.6133 (2)	0.5840 (9)	0.45991 (18)	0.0131 (12)
C34	0.5960 (2)	0.7561 (9)	0.4354 (2)	0.0170 (13)
H34	0.5578	0.7760	0.4270	0.020*
C35	0.6340 (3)	0.8974 (10)	0.4233 (2)	0.0191 (13)
H35	0.6220	1.0132	0.4062	0.023*
C36	0.7057 (2)	0.7111 (10)	0.4609 (2)	0.0198 (14)
H36	0.7438	0.6983	0.4704	0.024*
C37	0.6690 (2)	0.5647 (9)	0.4733 (2)	0.0160 (12)
H37	0.6819	0.4514	0.4909	0.019*
C38	0.7285 (3)	1.0258 (11)	0.4241 (2)	0.0287 (16)
H38A	0.7390	1.1123	0.4496	0.043*
H38B	0.7121	1.1112	0.4000	0.043*
H38C	0.7613	0.9567	0.4148	0.043*
C39	0.4407 (2)	−0.1190 (9)	0.34373 (19)	0.0141 (12)
C40	0.3846 (2)	−0.1374 (9)	0.3289 (2)	0.0165 (13)
H40	0.3575	−0.1257	0.3493	0.020*
C41	0.3686 (3)	−0.1720 (9)	0.2855 (2)	0.0194 (13)
H41	0.3306	−0.1852	0.2760	0.023*
C42	0.4608 (3)	−0.1704 (10)	0.2694 (2)	0.0212 (14)
H42	0.4871	−0.1805	0.2483	0.025*
C43	0.4784 (3)	−0.1387 (9)	0.3127 (2)	0.0197 (14)
H43	0.5168	−0.1302	0.3214	0.024*
C44	0.3891 (3)	−0.2322 (11)	0.2096 (2)	0.0309 (17)
H44A	0.4215	−0.2368	0.1927	0.046*
H44B	0.3639	−0.1246	0.1978	0.046*
H44C	0.3701	−0.3650	0.2075	0.046*
I1	0.195450 (15)	0.46659 (6)	0.048331 (12)	0.01785 (12)
I2	0.294854 (17)	0.24104 (7)	0.209298 (13)	0.02653 (13)
I3	0.52507 (2)	0.35907 (8)	0.235129 (16)	0.04044 (15)
I4	0.68215 (2)	0.99182 (7)	0.09052 (2)	0.04330 (16)
O1W	0.09764 (19)	0.8556 (8)	0.20744 (16)	0.0320 (11)
O2W	0.6112 (3)	0.6675 (15)	0.3155 (3)	0.088 (3)
O3W	0.7269 (5)	0.367 (2)	0.2106 (6)	0.075 (4)	0.50
O4W	0.6235 (5)	0.0915 (17)	0.3155 (3)	0.040 (3)	0.50
O5W	0.7152 (6)	0.225 (2)	0.2792 (6)	0.074 (4)	0.50
O6W	0.7762 (5)	0.078 (2)	0.1729 (7)	0.093 (6)	0.50

	U11	U22	U33	U12	U13	U23
N1	0.010 (2)	0.020 (3)	0.017 (3)	−0.001 (2)	0.0031 (19)	0.001 (2)
N2	0.010 (2)	0.021 (3)	0.018 (3)	−0.003 (2)	0.006 (2)	−0.002 (2)
N3	0.010 (2)	0.022 (3)	0.012 (2)	−0.001 (2)	0.0000 (19)	−0.002 (2)
N4	0.019 (3)	0.033 (3)	0.023 (3)	−0.008 (2)	0.004 (2)	−0.008 (3)
C1	0.012 (3)	0.018 (3)	0.018 (3)	0.004 (2)	0.005 (2)	−0.002 (3)
C2	0.019 (3)	0.018 (3)	0.017 (3)	0.001 (3)	0.007 (2)	−0.005 (3)
C3	0.013 (3)	0.021 (3)	0.018 (3)	0.000 (3)	0.006 (2)	0.001 (3)
C4	0.011 (3)	0.016 (3)	0.017 (3)	0.001 (2)	0.003 (2)	0.002 (3)
C5	0.010 (3)	0.016 (3)	0.015 (3)	0.004 (2)	0.005 (2)	0.004 (3)
C6	0.010 (3)	0.021 (3)	0.016 (3)	0.002 (2)	0.004 (2)	0.003 (3)
C7	0.010 (3)	0.023 (3)	0.019 (3)	−0.003 (3)	0.005 (2)	−0.002 (3)
C8	0.014 (3)	0.023 (3)	0.021 (3)	−0.004 (3)	0.002 (2)	−0.002 (3)
C9	0.014 (3)	0.019 (3)	0.019 (3)	0.000 (2)	−0.002 (2)	0.000 (3)
C10	0.009 (3)	0.018 (3)	0.022 (3)	0.001 (2)	0.004 (2)	0.003 (3)
C11	0.008 (3)	0.019 (3)	0.013 (3)	−0.004 (2)	0.001 (2)	−0.004 (2)
C12	0.012 (3)	0.015 (3)	0.014 (3)	0.000 (2)	0.003 (2)	0.004 (2)
C13	0.012 (3)	0.017 (3)	0.022 (3)	0.003 (2)	0.001 (2)	0.002 (3)
C14	0.017 (3)	0.017 (3)	0.012 (3)	−0.003 (3)	0.000 (2)	0.001 (2)
C15	0.012 (3)	0.019 (3)	0.018 (3)	0.003 (2)	−0.001 (2)	−0.002 (3)
C16	0.017 (3)	0.026 (4)	0.021 (3)	−0.004 (3)	0.008 (3)	0.002 (3)
C17	0.012 (3)	0.016 (3)	0.019 (3)	−0.003 (2)	0.006 (2)	0.000 (3)
C18	0.015 (3)	0.022 (3)	0.024 (3)	0.003 (3)	0.006 (3)	0.000 (3)
C19	0.019 (3)	0.029 (4)	0.020 (3)	0.002 (3)	−0.001 (3)	−0.006 (3)
C20	0.024 (3)	0.019 (3)	0.033 (4)	0.002 (3)	0.012 (3)	−0.006 (3)
C21	0.016 (3)	0.023 (3)	0.026 (4)	0.002 (3)	0.004 (3)	0.000 (3)
C22	0.040 (5)	0.048 (5)	0.046 (5)	−0.003 (4)	−0.001 (4)	−0.028 (4)
N5	0.010 (2)	0.012 (2)	0.014 (3)	−0.0003 (19)	0.0006 (19)	0.000 (2)
N6	0.010 (2)	0.015 (3)	0.010 (2)	−0.006 (2)	−0.0029 (18)	−0.001 (2)
N7	0.016 (3)	0.015 (3)	0.024 (3)	−0.006 (2)	0.007 (2)	−0.001 (2)
N8	0.031 (3)	0.017 (3)	0.011 (3)	−0.002 (2)	−0.007 (2)	−0.002 (2)
C23	0.014 (3)	0.015 (3)	0.012 (3)	0.000 (2)	0.000 (2)	0.000 (2)
C24	0.025 (3)	0.021 (3)	0.014 (3)	−0.004 (3)	0.000 (3)	0.001 (3)
C25	0.022 (3)	0.015 (3)	0.018 (3)	−0.005 (3)	0.000 (3)	0.002 (3)
C26	0.010 (3)	0.013 (3)	0.015 (3)	0.002 (2)	0.001 (2)	0.001 (2)
C27	0.012 (3)	0.010 (3)	0.017 (3)	−0.001 (2)	0.000 (2)	0.001 (2)
C28	0.006 (2)	0.012 (3)	0.016 (3)	0.000 (2)	−0.001 (2)	0.002 (2)
C29	0.010 (3)	0.015 (3)	0.019 (3)	0.000 (2)	0.000 (2)	−0.001 (2)
C30	0.014 (3)	0.013 (3)	0.014 (3)	0.000 (2)	−0.004 (2)	−0.001 (2)
C31	0.008 (3)	0.017 (3)	0.017 (3)	0.001 (2)	0.001 (2)	0.001 (2)
C32	0.013 (3)	0.014 (3)	0.012 (3)	0.002 (2)	0.001 (2)	−0.002 (2)
C33	0.012 (3)	0.014 (3)	0.013 (3)	−0.002 (2)	0.002 (2)	−0.005 (2)
C34	0.014 (3)	0.016 (3)	0.022 (3)	0.000 (2)	0.001 (2)	0.000 (3)
C35	0.021 (3)	0.014 (3)	0.023 (3)	0.001 (3)	0.003 (3)	0.000 (3)
C36	0.013 (3)	0.021 (3)	0.025 (3)	0.001 (3)	0.003 (3)	−0.003 (3)
C37	0.016 (3)	0.013 (3)	0.018 (3)	0.000 (2)	0.003 (2)	−0.003 (3)
C38	0.024 (4)	0.027 (4)	0.036 (4)	−0.009 (3)	0.009 (3)	0.002 (3)
C39	0.020 (3)	0.009 (3)	0.012 (3)	−0.001 (2)	−0.002 (2)	0.001 (2)
C40	0.017 (3)	0.014 (3)	0.017 (3)	−0.001 (2)	−0.005 (2)	0.005 (2)
C41	0.022 (3)	0.016 (3)	0.020 (3)	−0.001 (3)	−0.006 (3)	0.000 (3)
C42	0.030 (4)	0.018 (3)	0.016 (3)	−0.001 (3)	0.005 (3)	0.002 (3)
C43	0.020 (3)	0.017 (3)	0.021 (3)	−0.004 (3)	−0.003 (3)	0.000 (3)
C44	0.044 (4)	0.031 (4)	0.016 (3)	0.002 (3)	−0.006 (3)	−0.005 (3)
I1	0.0156 (2)	0.0166 (2)	0.0208 (2)	−0.00044 (15)	−0.00111 (15)	0.00148 (15)
I2	0.0291 (2)	0.0267 (2)	0.0232 (2)	−0.00046 (18)	−0.00126 (17)	0.00460 (17)
I3	0.0449 (3)	0.0435 (3)	0.0363 (3)	0.0162 (2)	0.0227 (2)	0.0111 (2)
I4	0.0381 (3)	0.0211 (2)	0.0761 (4)	0.0003 (2)	0.0356 (3)	0.0008 (2)
O1W	0.028 (3)	0.035 (3)	0.033 (3)	0.001 (2)	0.005 (2)	−0.006 (2)
O2W	0.060 (5)	0.111 (7)	0.094 (6)	0.011 (5)	0.015 (4)	0.032 (5)
O3W	0.026 (5)	0.054 (6)	0.141 (9)	0.004 (5)	−0.019 (6)	0.042 (7)
O4W	0.051 (6)	0.040 (6)	0.029 (6)	0.011 (5)	0.004 (5)	0.001 (5)
O5W	0.051 (8)	0.045 (8)	0.125 (13)	−0.007 (6)	0.004 (8)	−0.009 (8)
O6W	0.038 (7)	0.067 (10)	0.164 (17)	−0.012 (7)	−0.054 (9)	0.029 (10)

N1—C1	1.368 (8)	N5—C26	1.367 (8)
N1—C4	1.373 (8)	N5—C23	1.373 (7)
N2—C6	1.367 (8)	N6—C31	1.367 (8)
N2—C9	1.370 (8)	N6—C28	1.371 (8)
N2—H2	0.8800	N6—H6	0.8800
N3—C13	1.334 (8)	N7—C36	1.347 (8)
N3—C14	1.337 (8)	N7—C35	1.350 (8)
N3—C16	1.480 (8)	N7—C38	1.471 (8)
N4—C20	1.337 (9)	N8—C42	1.344 (8)
N4—C19	1.339 (9)	N8—C41	1.347 (9)
N4—C22	1.481 (9)	N8—C44	1.484 (8)
C1—C10	1.414 (8)	C23—C32	1.417 (8)
C1—C2	1.454 (8)	C23—C24	1.450 (9)
C2—C3	1.347 (9)	C24—C25	1.348 (9)
C2—H2A	0.9500	C24—H24	0.9500
C3—C4	1.458 (9)	C25—C26	1.446 (9)
C3—H3	0.9500	C25—H25	0.9500
C4—C5	1.401 (9)	C26—C27	1.413 (8)
C5—C6	1.401 (9)	C27—C28	1.388 (8)
C5—C11	1.490 (8)	C27—C33	1.499 (8)
C6—C7	1.426 (9)	C28—C29	1.428 (8)
C7—C8	1.353 (9)	C29—C30	1.358 (9)
C7—H7	0.9500	C29—H29	0.9500
C8—C9	1.442 (9)	C30—C31	1.429 (8)
C8—H8	0.9500	C30—H30	0.9500
C9—C10i	1.384 (9)	C31—C32ii	1.394 (9)
C10—C9i	1.384 (9)	C32—C31ii	1.394 (9)
C10—C17	1.489 (9)	C32—C39	1.480 (8)
C11—C15	1.375 (9)	C33—C37	1.386 (8)
C11—C12	1.402 (8)	C33—C34	1.394 (9)
C12—C13	1.378 (9)	C34—C35	1.379 (9)
C12—H12	0.9500	C34—H34	0.9500
C13—H13	0.9500	C35—H35	0.9500
C14—C15	1.385 (9)	C36—C37	1.382 (9)
C14—H14	0.9500	C36—H36	0.9500
C15—H15	0.9500	C37—H37	0.9500
C16—H16A	0.9800	C38—H38A	0.9800
C16—H16B	0.9800	C38—H38B	0.9800
C16—H16C	0.9800	C38—H38C	0.9800
C17—C18	1.393 (9)	C39—C43	1.383 (9)
C17—C21	1.395 (9)	C39—C40	1.404 (8)
C18—C19	1.367 (9)	C40—C41	1.368 (9)
C18—H18	0.9500	C40—H40	0.9500
C19—H19	0.9500	C41—H41	0.9500
C20—C21	1.376 (10)	C42—C43	1.372 (9)
C20—H20	0.9500	C42—H42	0.9500
C21—H21	0.9500	C43—H43	0.9500
C22—H22A	0.9800	C44—H44A	0.9800
C22—H22B	0.9800	C44—H44B	0.9800
C22—H22C	0.9800	C44—H44C	0.9800
O2W···O4Wiii	2.781 (15)	O2W···I3	3.684 (9)
O2W···O6Wiv	2.793 (15)	O6W···I4vi	3.299 (18)
O3W···O5Wiv	2.730 (19)	C13···I1	3.691 (6)
O3W···O6W	2.56 (2)	C14···I2vi	3.760 (6)
O4W···O5W	2.721 (19)	C44···I2	3.844 (7)
O5W···O6Wiv	2.73 (2)	C22···I3iii	3.882 (7)
O1W···I2v	3.565 (5)	C36···I4vii	3.566 (5)
O1W···I3v	3.594 (5)
C1—N1—C4	105.2 (5)	C26—N5—C23	104.4 (5)
C6—N2—C9	110.0 (5)	C31—N6—C28	110.2 (5)
C6—N2—H2	125.0	C31—N6—H6	124.9
C9—N2—H2	125.0	C28—N6—H6	124.9
C13—N3—C14	121.3 (5)	C36—N7—C35	120.6 (5)
C13—N3—C16	119.4 (5)	C36—N7—C38	119.1 (5)
C14—N3—C16	119.2 (5)	C35—N7—C38	120.2 (5)
C20—N4—C19	121.1 (6)	C42—N8—C41	120.8 (5)
C20—N4—C22	120.4 (6)	C42—N8—C44	119.7 (6)
C19—N4—C22	118.5 (6)	C41—N8—C44	119.5 (5)
N1—C1—C10	125.1 (5)	N5—C23—C32	124.4 (5)
N1—C1—C2	111.0 (5)	N5—C23—C24	111.2 (5)
C10—C1—C2	123.8 (6)	C32—C23—C24	124.2 (5)
C3—C2—C1	106.6 (5)	C25—C24—C23	106.3 (5)
C3—C2—H2A	126.7	C25—C24—H24	126.8
C1—C2—H2A	126.7	C23—C24—H24	126.8
C2—C3—C4	106.5 (5)	C24—C25—C26	106.4 (5)
C2—C3—H3	126.7	C24—C25—H25	126.8
C4—C3—H3	126.7	C26—C25—H25	126.8
N1—C4—C5	125.8 (5)	N5—C26—C27	124.0 (5)
N1—C4—C3	110.7 (5)	N5—C26—C25	111.5 (5)
C5—C4—C3	123.3 (5)	C27—C26—C25	124.5 (5)
C6—C5—C4	126.4 (5)	C28—C27—C26	126.9 (5)
C6—C5—C11	116.9 (5)	C28—C27—C33	115.7 (5)
C4—C5—C11	116.7 (5)	C26—C27—C33	117.4 (5)
N2—C6—C5	125.1 (5)	N6—C28—C27	126.2 (5)
N2—C6—C7	107.1 (5)	N6—C28—C29	106.6 (5)
C5—C6—C7	127.8 (5)	C27—C28—C29	127.1 (5)
C8—C7—C6	108.4 (5)	C30—C29—C28	108.2 (5)
C8—C7—H7	125.8	C30—C29—H29	125.9
C6—C7—H7	125.8	C28—C29—H29	125.9
C7—C8—C9	107.7 (6)	C29—C30—C31	108.0 (5)
C7—C8—H8	126.1	C29—C30—H30	126.0
C9—C8—H8	126.1	C31—C30—H30	126.0
N2—C9—C10i	126.6 (6)	N6—C31—C32ii	125.8 (5)
N2—C9—C8	106.7 (5)	N6—C31—C30	106.8 (5)
C10i—C9—C8	126.7 (6)	C32ii—C31—C30	127.4 (5)
C9i—C10—C1	126.2 (6)	C31ii—C32—C23	126.5 (5)
C9i—C10—C17	116.7 (5)	C31ii—C32—C39	115.8 (5)
C1—C10—C17	116.7 (5)	C23—C32—C39	117.7 (5)
C15—C11—C12	117.9 (5)	C37—C33—C34	118.4 (5)
C15—C11—C5	122.0 (5)	C37—C33—C27	119.1 (5)
C12—C11—C5	120.1 (5)	C34—C33—C27	122.5 (5)
C13—C12—C11	119.8 (5)	C35—C34—C33	120.2 (5)
C13—C12—H12	120.1	C35—C34—H34	119.9
C11—C12—H12	120.1	C33—C34—H34	119.9
N3—C13—C12	120.4 (5)	N7—C35—C34	120.2 (6)
N3—C13—H13	119.8	N7—C35—H35	119.9
C12—C13—H13	119.8	C34—C35—H35	119.9
N3—C14—C15	120.2 (6)	N7—C36—C37	121.0 (5)
N3—C14—H14	119.9	N7—C36—H36	119.5
C15—C14—H14	119.9	C37—C36—H36	119.5
C11—C15—C14	120.2 (6)	C36—C37—C33	119.6 (6)
C11—C15—H15	119.9	C36—C37—H37	120.2
C14—C15—H15	119.9	C33—C37—H37	120.2
N3—C16—H16A	109.5	N7—C38—H38A	109.5
N3—C16—H16B	109.5	N7—C38—H38B	109.5
H16A—C16—H16B	109.5	H38A—C38—H38B	109.5
N3—C16—H16C	109.5	N7—C38—H38C	109.5
H16A—C16—H16C	109.5	H38A—C38—H38C	109.5
H16B—C16—H16C	109.5	H38B—C38—H38C	109.5
C18—C17—C21	117.7 (6)	C43—C39—C40	117.1 (5)
C18—C17—C10	118.3 (5)	C43—C39—C32	121.7 (5)
C21—C17—C10	124.0 (5)	C40—C39—C32	121.2 (5)
C19—C18—C17	120.4 (6)	C41—C40—C39	120.8 (6)
C19—C18—H18	119.8	C41—C40—H40	119.6
C17—C18—H18	119.8	C39—C40—H40	119.6
N4—C19—C18	120.4 (6)	N8—C41—C40	120.0 (6)
N4—C19—H19	119.8	N8—C41—H41	120.0
C18—C19—H19	119.8	C40—C41—H41	120.0
N4—C20—C21	121.0 (6)	N8—C42—C43	120.9 (6)
N4—C20—H20	119.5	N8—C42—H42	119.6
C21—C20—H20	119.5	C43—C42—H42	119.6
C20—C21—C17	119.4 (6)	C42—C43—C39	120.4 (6)
C20—C21—H21	120.3	C42—C43—H43	119.8
C17—C21—H21	120.3	C39—C43—H43	119.8
N4—C22—H22A	109.5	N8—C44—H44A	109.5
N4—C22—H22B	109.5	N8—C44—H44B	109.5
H22A—C22—H22B	109.5	H44A—C44—H44B	109.5
N4—C22—H22C	109.5	N8—C44—H44C	109.5
H22A—C22—H22C	109.5	H44A—C44—H44C	109.5
H22B—C22—H22C	109.5	H44B—C44—H44C	109.5
C4—N1—C1—C10	178.6 (6)	C26—N5—C23—C32	175.1 (5)
C4—N1—C1—C2	1.9 (6)	C26—N5—C23—C24	−1.3 (6)
N1—C1—C2—C3	−2.4 (7)	N5—C23—C24—C25	2.6 (7)
C10—C1—C2—C3	−179.2 (6)	C32—C23—C24—C25	−173.8 (6)
C1—C2—C3—C4	1.9 (7)	C23—C24—C25—C26	−2.7 (7)
C1—N1—C4—C5	−175.4 (6)	C23—N5—C26—C27	−179.2 (5)
C1—N1—C4—C3	−0.6 (6)	C23—N5—C26—C25	−0.5 (6)
C2—C3—C4—N1	−0.9 (7)	C24—C25—C26—N5	2.1 (7)
C2—C3—C4—C5	174.0 (6)	C24—C25—C26—C27	−179.2 (6)
N1—C4—C5—C6	3.3 (10)	N5—C26—C27—C28	−5.3 (9)
C3—C4—C5—C6	−170.8 (6)	C25—C26—C27—C28	176.2 (6)
N1—C4—C5—C11	−176.9 (5)	N5—C26—C27—C33	172.4 (5)
C3—C4—C5—C11	9.0 (8)	C25—C26—C27—C33	−6.1 (8)
C9—N2—C6—C5	−176.4 (6)	C31—N6—C28—C27	177.9 (5)
C9—N2—C6—C7	3.0 (7)	C31—N6—C28—C29	−3.5 (6)
C4—C5—C6—N2	−1.5 (10)	C26—C27—C28—N6	11.1 (9)
C11—C5—C6—N2	178.8 (5)	C33—C27—C28—N6	−166.7 (5)
C4—C5—C6—C7	179.3 (6)	C26—C27—C28—C29	−167.3 (6)
C11—C5—C6—C7	−0.5 (9)	C33—C27—C28—C29	14.9 (8)
N2—C6—C7—C8	−2.3 (7)	N6—C28—C29—C30	1.0 (6)
C5—C6—C7—C8	177.1 (6)	C27—C28—C29—C30	179.6 (5)
C6—C7—C8—C9	0.7 (7)	C28—C29—C30—C31	1.7 (6)
C6—N2—C9—C10i	175.5 (6)	C28—N6—C31—C32ii	−177.0 (5)
C6—N2—C9—C8	−2.5 (7)	C28—N6—C31—C30	4.5 (6)
C7—C8—C9—N2	1.1 (7)	C29—C30—C31—N6	−3.8 (6)
C7—C8—C9—C10i	−177.0 (6)	C29—C30—C31—C32ii	177.7 (6)
N1—C1—C10—C9i	1.2 (10)	N5—C23—C32—C31ii	−0.5 (9)
C2—C1—C10—C9i	177.5 (6)	C24—C23—C32—C31ii	175.4 (6)
N1—C1—C10—C17	−170.6 (6)	N5—C23—C32—C39	−178.4 (5)
C2—C1—C10—C17	5.7 (9)	C24—C23—C32—C39	−2.5 (9)
C6—C5—C11—C15	65.1 (7)	C28—C27—C33—C37	58.3 (7)
C4—C5—C11—C15	−114.7 (6)	C26—C27—C33—C37	−119.7 (6)
C6—C5—C11—C12	−115.8 (6)	C28—C27—C33—C34	−122.1 (6)
C4—C5—C11—C12	64.4 (7)	C26—C27—C33—C34	59.9 (8)
C15—C11—C12—C13	3.5 (8)	C37—C33—C34—C35	2.9 (9)
C5—C11—C12—C13	−175.7 (5)	C27—C33—C34—C35	−176.7 (6)
C14—N3—C13—C12	−2.2 (8)	C36—N7—C35—C34	−1.7 (9)
C16—N3—C13—C12	−180.0 (5)	C38—N7—C35—C34	−178.0 (6)
C11—C12—C13—N3	−1.4 (9)	C33—C34—C35—N7	−1.0 (9)
C13—N3—C14—C15	3.7 (8)	C35—N7—C36—C37	2.5 (9)
C16—N3—C14—C15	−178.6 (5)	C38—N7—C36—C37	178.9 (6)
C12—C11—C15—C14	−2.1 (8)	N7—C36—C37—C33	−0.5 (9)
C5—C11—C15—C14	177.1 (5)	C34—C33—C37—C36	−2.1 (9)
N3—C14—C15—C11	−1.4 (9)	C27—C33—C37—C36	177.5 (5)
C9i—C10—C17—C18	−64.2 (8)	C31ii—C32—C39—C43	−120.9 (6)
C1—C10—C17—C18	108.5 (6)	C23—C32—C39—C43	57.2 (8)
C9i—C10—C17—C21	116.3 (7)	C31ii—C32—C39—C40	58.8 (7)
C1—C10—C17—C21	−71.0 (8)	C23—C32—C39—C40	−123.0 (6)
C21—C17—C18—C19	1.6 (9)	C43—C39—C40—C41	−0.4 (9)
C10—C17—C18—C19	−177.9 (6)	C32—C39—C40—C41	179.8 (6)
C20—N4—C19—C18	−0.3 (10)	C42—N8—C41—C40	0.5 (9)
C22—N4—C19—C18	−177.4 (7)	C44—N8—C41—C40	177.8 (6)
C17—C18—C19—N4	−1.1 (10)	C39—C40—C41—N8	−0.5 (9)
C19—N4—C20—C21	1.2 (10)	C41—N8—C42—C43	0.5 (9)
C22—N4—C20—C21	178.2 (7)	C44—N8—C42—C43	−176.9 (6)
N4—C20—C21—C17	−0.6 (10)	N8—C42—C43—C39	−1.4 (9)
C18—C17—C21—C20	−0.7 (9)	C40—C39—C43—C42	1.3 (9)
C10—C17—C21—C20	178.8 (6)	C32—C39—C43—C42	−178.9 (6)

Table 1

Selected interatomic distances (Å)

O2W⋯O4Wi	2.781 (15)
O2W⋯O6Wii	2.793 (15)
O3W⋯O5Wii	2.730 (19)
O3W⋯O6W	2.56 (2)
O4W⋯O5W	2.721 (19)
O5W⋯O6Wii	2.73 (2)
O1W⋯I2iii	3.565 (5)
O1W⋯I3iii	3.594 (5)
O2W⋯I3	3.684 (9)
O6W⋯I4iv	3.299 (18)
C13⋯I1	3.691 (6)
C14⋯I2iv	3.760 (6)
C44⋯I2	3.844 (7)
C22⋯I3i	3.882 (7)
C36⋯I4v	3.566 (5)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .