A perchlorate salt of an octaprotonated cryptand

The title compound, 1,4,8,11,14,18,23,27-octa­aza-6,16,25(2,6)- tripyridinabi­cyclo­[9.9.9]­nonacosaphane(8+) octaperchlorate pen­ta­hydrate, C₃₃H₅₉N₁₁⁸⁺·8ClO₄^-·5H₂O, is a salt of an octaprotonated cryptand in which one of the pyridine groups and the bridgehead tertiary amines remain unprotonated. The central cavity of the cryptand is not occupied, although the perchlorate ions are hydrogen bonded in clefts formed between the arms of the cryptand.

S1. Comment

Protonated aminocryptands have previously been shown to be versatile hosts for polyatomic oxoanions (Morgan et al., 1995; Hynes et al., 2000; Maubert et al., 2001; Farrell et al., 2003). In these examples, either one or two anions are encapsulated within the cavity of the cryptand, most commonly by a mixture of direct (anion-protonated amine) and indirect (anion–water-protonated amine) hydrogen bonding. The hexaprotonated form of the pyridine-containing cryptand L has been shown to bind a single SiF₆²⁻ ion within the cavity via six (amine)NH···F hydrogen bonds, while four BF₄⁻ ions are located in the lattice but clearly outside the host.

In contrast, the octaprotonated form of the host in the title compound, (I), binds three of the perchlorate anions in sites within clefts formed between the arms [## AUTHOR - change OK? ##] of the cryptand.

Fig. 1 shows the conformation of the protonated cryptand. The six secondary amine groups are protonated, but the tertiary amines of the bridgeheads (N1 and N2) are not. Two of the pyridine groups are protonated (at N4A and N4C), and the planes of these rings are aligned tangentially to the body of the cryptand and are almost parallel to each other (Fig. 2). The hydrogen atoms attached to N4A and N4C were located from difference maps, and there is further support for this assignment in the observation of hydrogen bonding between these two pyridine groups and perchlorate O atoms.

Protonation of the pyridine rings rather than the bridgehead N atoms would be surprising if the pK_a values of these groups were close to those of free pyridine and triethylamine (pK_a = 5.25 and 11.01, respectively). Within the constraints the cage framework, however, this assumption appears not to hold. In part, this behaviour may be due to some flattening of the tetrahedral geometry at the bridgehead N atoms, which reflects a tendency towards sp² hybridization and therefore a decrease in basicity. However, geometric evidence for sp² hybridization is slight; the angle sums at N1 and N2 are 338 (8) and 337 (9)°, respectively. An alternative possibility is that, since protonation is stabilized by hydrogen bonding, the observed protonation pattern is a consequence of the hydrogen bonding in the lattice.

As with other reported anion cryptates (Morgan et al., 1995; Hynes et al., 2000; Maubert et al., 2001; Farrell et al., 2003) the hydrogen-bonding network linking cation, anions and solvate water molecules is complex. The individual hydrogen bonds are listed in Table 1, while Fig. 2 illustrates the binding of the three perchlorate anions most closely associated with the clefts between the arms of the cryptand. Each of the eight perchlorate anions forms at least one hydrogen bond to a protonated group of the cryptand, and each cryptand NH₂⁺ ion forms at least two hydrogen bonds (some are bifurcated) to O atoms of either perchlorate or water. The solvate water molecules facilitate further hydrogen-bonding interactions that extend through the lattice.

The hexaprotonated analogue of the cryptand can selectively encapsulate SiF₆²⁻ in preference to BF₄⁻ (Morgan et al., 1995). Although this observation can be partly explained on the basis of charge selectivity, taken in tandem with the present result this preference might also suggest that the cryptand does not favour tetrahedral guests. However, as it is equally possible that the octaprotonated cryptand adopts this geometry to maximize the hydrogen bonding and hence minimize the energy of the structure, the structures of other hexa- or octaprotonated cryptates of this ligand will be of much interest.

S2. Experimental

The neutral cryptand was prepared by the literature method (Marrs et al., 1993). It was then dissolved in ethanol and perchloric acid was added until the pH was approximately 2. Colourless crystals of the complex crystallized out of this solution over approximately two weeks.

S3. Refinement

H atoms bonded to C atoms or amine N atoms were inserted at calculated positions; those bonded to O atoms or to the pyridine N atoms were located from difference maps. The constrained C—H distances were 0.95, 0.99 and 0.92 Å for aryl, methylene and amine H atoms, respectively, with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: XSCANS (Siemens, 1990a); cell refinement: XSCANS (Siemens, 1990a); data reduction: XSCANS (Siemens, 1990a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

	Fig. 1. A perspective view of the title cation showing 50% probability displacement ellipsoids. H atoms bonded to C atoms have been omitted for clarity.
	Fig. 2. A perspective diagram showing the three perchlorate anions hydrogen bonded into the clefts between strands of the protonated cryptand. Hydrogen bonds are shown as dashed lines.
	Fig. 3. A projection of the unit cell along a with hydrogen bonds shown as dashed lines.

(I)

Crystal data

C33H59N11^8+·8ClO4^−·5H2O	Z = 2
Mr = 1495.59	F(000) = 1552
Triclinic, P1	Dx = 1.719 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.9265 (13) Å	Cell parameters from 36 reflections
b = 13.6798 (14) Å	θ = 4.5–12.5°
c = 18.5310 (19) Å	µ = 0.50 mm^−1
α = 84.258 (9)°	T = 128 K
β = 76.394 (8)°	Block, colourless
γ = 65.092 (8)°	0.82 × 0.52 × 0.36 mm
V = 2888.7 (6) Å^3

Data collection

Siemens P4 diffractometer	7315 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.105
Graphite monochromator	θmax = 24.0°, θmin = 2.3°
ω scans	h = 0→14
Absorption correction: ψ scan (SHELXTL/PC; Siemens, 1990b)	k = −14→15
Tmin = 0.862, Tmax = 0.972	l = −20→21
9513 measured reflections	3 standard reflections every 97 reflections
9055 independent reflections	intensity decay: none

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.058P)^2 + 4.792P] where P = (Fo^2 + 2Fc^2)/3
9055 reflections	(Δ/σ)max = 0.001
838 parameters	Δρmax = 0.65 e Å^−3
0 restraints	Δρmin = −0.67 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. The structure was solved by direct methods (Sheldrick, 1990), and all the non-H atoms were refined with anisotropic atomic displacement parameters.

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

	x	y	z	Uiso*/Ueq
N1	1.2799 (2)	0.5830 (2)	0.19115 (14)	0.0124 (6)
C1A	1.3201 (3)	0.6256 (3)	0.11925 (18)	0.0146 (7)
H1A1	1.3729	0.5650	0.0850	0.018*
H1A2	1.3647	0.6664	0.1262	0.018*
C2A	1.2179 (3)	0.6988 (3)	0.08536 (18)	0.0159 (7)
H2A1	1.1697	0.6599	0.0819	0.019*
H2A2	1.1684	0.7626	0.1175	0.019*
N3A	1.2608 (2)	0.7344 (2)	0.00966 (14)	0.0142 (6)
H3A1	1.3024	0.6749	−0.0206	0.017*
H3A2	1.3109	0.7648	0.0129	0.017*
C3A	1.1640 (3)	0.8144 (3)	−0.02510 (18)	0.0164 (7)
H3A3	1.1973	0.8305	−0.0763	0.020*
H3A4	1.1260	0.8824	0.0036	0.020*
C4A	1.0738 (3)	0.7727 (3)	−0.02723 (17)	0.0134 (7)
C5A	1.0915 (3)	0.6930 (3)	−0.07367 (19)	0.0190 (8)
H5A	1.1627	0.6627	−0.1092	0.023*
C6A	1.0050 (3)	0.6567 (3)	−0.0686 (2)	0.0214 (8)
H6A	1.0180	0.5999	−0.0999	0.026*
C7A	0.8990 (3)	0.7028 (3)	−0.01793 (19)	0.0198 (8)
H7A	0.8397	0.6777	−0.0142	0.024*
C8A	0.8819 (3)	0.7851 (3)	0.02657 (18)	0.0143 (7)
N4A	0.9700 (2)	0.8158 (2)	0.02143 (15)	0.0143 (6)
H4A	0.961 (3)	0.865 (3)	0.050 (2)	0.017*
C9A	0.7710 (3)	0.8482 (3)	0.08157 (19)	0.0176 (7)
H9A1	0.7911	0.8729	0.1227	0.021*
H9A2	0.7220	0.9129	0.0567	0.021*
N5A	0.7023 (2)	0.7828 (2)	0.11291 (15)	0.0167 (6)
H5A1	0.7478	0.7237	0.1368	0.020*
H5A2	0.6862	0.7582	0.0743	0.020*
C10A	0.5893 (3)	0.8430 (3)	0.16644 (19)	0.0216 (8)
H10A	0.5446	0.7978	0.1787	0.026*
H10B	0.5424	0.9095	0.1421	0.026*
C11A	0.6066 (3)	0.8732 (3)	0.23727 (19)	0.0209 (8)
H11A	0.6501	0.9195	0.2249	0.025*
H11B	0.5292	0.9162	0.2683	0.025*
N2	0.6704 (2)	0.7797 (2)	0.28121 (15)	0.0166 (6)
C1B	1.2025 (3)	0.6671 (3)	0.24645 (18)	0.0147 (7)
H1B1	1.1829	0.6311	0.2934	0.018*
H1B2	1.1288	0.7086	0.2293	0.018*
C2B	1.2479 (3)	0.7472 (3)	0.26366 (18)	0.0146 (7)
H2B1	1.3192	0.7094	0.2839	0.018*
H2B2	1.2662	0.7868	0.2183	0.018*
N3B	1.1505 (2)	0.8227 (2)	0.32019 (15)	0.0146 (6)
H3B1	1.0843	0.8516	0.3009	0.017*
H3B2	1.1361	0.7830	0.3613	0.017*
C3B	1.1689 (3)	0.9128 (3)	0.34500 (19)	0.0168 (7)
H3B3	1.2039	0.9458	0.3017	0.020*
H3B4	1.2231	0.8855	0.3794	0.020*
C4B	1.0518 (3)	0.9968 (3)	0.38403 (18)	0.0152 (7)
C5B	1.0453 (3)	1.0803 (3)	0.42379 (18)	0.0181 (7)
H5B	1.1143	1.0854	0.4290	0.022*
C6B	0.9363 (3)	1.1561 (3)	0.45574 (18)	0.0200 (8)
H6B	0.9292	1.2139	0.4838	0.024*
C7B	0.8375 (3)	1.1468 (3)	0.44642 (18)	0.0190 (8)
H7B	0.7617	1.1980	0.4678	0.023*
C8B	0.8519 (3)	1.0612 (3)	0.40520 (17)	0.0152 (7)
N4B	0.9575 (2)	0.9865 (2)	0.37408 (14)	0.0149 (6)
C9B	0.7490 (3)	1.0478 (3)	0.39027 (19)	0.0188 (7)
H9B1	0.6795	1.0833	0.4301	0.023*
H9B2	0.7316	1.0826	0.3425	0.023*
N5B	0.7752 (2)	0.9310 (2)	0.38721 (17)	0.0199 (6)
H5B1	0.7833	0.9013	0.4334	0.024*
H5B2	0.8455	0.8973	0.3547	0.024*
C10B	0.6842 (3)	0.9084 (3)	0.3636 (2)	0.0219 (8)
H10C	0.6406	0.9691	0.3335	0.026*
H10D	0.6283	0.9001	0.4079	0.026*
C11B	0.7444 (3)	0.8049 (3)	0.31789 (19)	0.0167 (7)
H11C	0.8097	0.8101	0.2795	0.020*
H11D	0.7787	0.7440	0.3509	0.020*
C1C	1.3802 (3)	0.4979 (3)	0.21638 (18)	0.0151 (7)
H1C1	1.4259	0.5311	0.2325	0.018*
H1C2	1.4314	0.4491	0.1744	0.018*
C2C	1.3426 (3)	0.4326 (3)	0.28035 (18)	0.0151 (7)
H2C1	1.4110	0.3661	0.2875	0.018*
H2C2	1.3116	0.4753	0.3267	0.018*
N3C	1.2513 (2)	0.4036 (2)	0.26461 (15)	0.0134 (6)
H3C1	1.2745	0.3768	0.2171	0.016*
H3C2	1.1830	0.4646	0.2672	0.016*
C3C	1.2293 (3)	0.3211 (3)	0.31843 (18)	0.0149 (7)
H3C3	1.2997	0.2521	0.3116	0.018*
H3C4	1.2126	0.3460	0.3699	0.018*
C4C	1.1276 (3)	0.3040 (2)	0.30575 (17)	0.0135 (7)
C5C	1.1377 (3)	0.2259 (3)	0.26024 (18)	0.0176 (7)
H5C	1.2128	0.1767	0.2359	0.021*
C6C	1.0387 (3)	0.2187 (3)	0.24987 (18)	0.0192 (8)
H6C	1.0454	0.1647	0.2184	0.023*
C7C	0.9286 (3)	0.2914 (3)	0.28591 (19)	0.0181 (7)
H7C	0.8601	0.2870	0.2791	0.022*
C8C	0.9199 (3)	0.3694 (3)	0.33130 (17)	0.0144 (7)
N4C	1.0195 (2)	0.3721 (2)	0.34011 (15)	0.0134 (6)
H4C	1.014 (3)	0.415 (3)	0.370 (2)	0.016*
C9C	0.8069 (3)	0.4511 (3)	0.37432 (18)	0.0170 (7)
H9C1	0.7496	0.4185	0.3893	0.020*
H9C2	0.8207	0.4709	0.4200	0.020*
N5C	0.7568 (2)	0.5513 (2)	0.32931 (15)	0.0163 (6)
H5C1	0.8136	0.5761	0.3095	0.020*
H5C2	0.7335	0.5349	0.2906	0.020*
C10C	0.6542 (3)	0.6384 (3)	0.37627 (19)	0.0182 (7)
H10E	0.6816	0.6625	0.4139	0.022*
H10F	0.5980	0.6085	0.4029	0.022*
C11C	0.5921 (3)	0.7354 (3)	0.33007 (19)	0.0188 (7)
H11E	0.5524	0.7138	0.2991	0.023*
H11F	0.5312	0.7929	0.3641	0.023*
Cl1	1.37126 (7)	0.44076 (6)	−0.05127 (4)	0.01683 (19)
O1A	1.2532 (2)	0.4612 (2)	−0.01323 (15)	0.0336 (7)
O1B	1.4501 (2)	0.3878 (2)	−0.00286 (13)	0.0239 (6)
O1C	1.4030 (2)	0.37490 (19)	−0.11585 (14)	0.0261 (6)
O1D	1.3781 (2)	0.54202 (19)	−0.07669 (13)	0.0233 (6)
Cl2	0.94428 (7)	0.99198 (6)	0.18214 (4)	0.01594 (18)
O2A	0.8699 (2)	0.9430 (2)	0.22414 (15)	0.0314 (6)
O2B	1.0586 (2)	0.9374 (2)	0.19777 (14)	0.0310 (6)
O2C	0.8974 (2)	1.10376 (19)	0.19951 (14)	0.0255 (6)
O2D	0.9531 (2)	0.98124 (19)	0.10332 (13)	0.0227 (6)
Cl3	0.98709 (7)	0.62850 (6)	0.43328 (4)	0.01363 (18)
O3A	0.8786 (2)	0.6209 (2)	0.43590 (15)	0.0290 (6)
O3B	0.9844 (2)	0.72802 (18)	0.39691 (13)	0.0194 (5)
O3C	1.0804 (2)	0.53829 (18)	0.39068 (13)	0.0230 (6)
O3D	1.0064 (2)	0.62624 (19)	0.50605 (13)	0.0228 (6)
Cl4	0.97261 (7)	0.59593 (6)	0.17288 (4)	0.01566 (18)
O4A	0.9996 (2)	0.5509 (2)	0.24295 (15)	0.0318 (6)
O4B	0.8694 (2)	0.58444 (19)	0.16525 (13)	0.0206 (5)
O4C	1.0661 (2)	0.5418 (2)	0.11188 (15)	0.0303 (6)
O4D	0.9510 (2)	0.70784 (19)	0.17057 (13)	0.0229 (6)
Cl5	0.69858 (7)	1.03231 (7)	−0.09514 (5)	0.0203 (2)
O5A	0.6576 (3)	1.1469 (2)	−0.08597 (16)	0.0344 (7)
O5B	0.6089 (2)	1.0002 (2)	−0.05227 (15)	0.0284 (6)
O5C	0.7176 (3)	1.0104 (2)	−0.17190 (15)	0.0376 (7)
O5D	0.8029 (2)	0.9788 (3)	−0.06772 (18)	0.0490 (9)
Cl6	1.35913 (7)	0.58201 (6)	0.43736 (4)	0.01733 (19)
O6A	1.2492 (2)	0.6631 (2)	0.42476 (14)	0.0268 (6)
O6B	1.3926 (2)	0.6169 (2)	0.49442 (15)	0.0303 (6)
O6C	1.3431 (2)	0.4842 (2)	0.46069 (14)	0.0279 (6)
O6D	1.4463 (2)	0.5617 (2)	0.36967 (14)	0.0295 (6)
Cl7	0.64390 (7)	0.92975 (7)	0.58632 (5)	0.0202 (2)
O7A	0.7477 (2)	0.8545 (2)	0.53767 (15)	0.0296 (6)
O7B	0.6766 (2)	0.9483 (2)	0.65039 (15)	0.0386 (7)
O7C	0.5948 (2)	1.0285 (2)	0.54793 (16)	0.0400 (8)
O7D	0.5606 (2)	0.8828 (2)	0.60946 (17)	0.0370 (7)
Cl8	1.56932 (8)	0.16959 (7)	0.16125 (5)	0.0274 (2)
O8A	1.6162 (4)	0.1036 (4)	0.0987 (3)	0.112 (2)
O8B	1.6305 (4)	0.1187 (4)	0.2171 (3)	0.0980 (17)
O8C	1.5882 (3)	0.2652 (2)	0.1430 (2)	0.0741 (13)
O8D	1.4497 (3)	0.1949 (3)	0.1874 (2)	0.0591 (10)
O1W	1.2523 (3)	0.3431 (2)	0.13165 (15)	0.0289 (6)
H1WA	1.215 (4)	0.403 (4)	0.112 (2)	0.035*
H1WB	1.311 (4)	0.283 (4)	0.108 (2)	0.035*
O2W	0.6074 (2)	0.7995 (2)	−0.01119 (14)	0.0240 (6)
H2WA	0.597 (3)	0.865 (4)	−0.025 (2)	0.029*
H2WB	0.544 (4)	0.799 (3)	−0.008 (2)	0.029*
O3W	0.6914 (3)	0.4730 (3)	0.23071 (16)	0.0320 (7)
H3WA	0.655 (4)	0.507 (4)	0.199 (3)	0.038*
H3WB	0.670 (4)	0.418 (4)	0.240 (2)	0.038*
O4W	0.6624 (3)	0.2979 (3)	0.2898 (2)	0.0404 (8)
H4WA	0.612 (4)	0.309 (4)	0.336 (3)	0.048*
H4WB	0.654 (4)	0.265 (4)	0.260 (3)	0.048*
O5W	0.4815 (3)	0.7277 (3)	0.58189 (19)	0.0414 (8)
H5WA	0.533 (4)	0.668 (4)	0.564 (3)	0.050*
H5WB	0.520 (4)	0.762 (4)	0.592 (3)	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0113 (13)	0.0113 (14)	0.0091 (13)	−0.0032 (11)	0.0053 (11)	−0.0003 (11)
C1A	0.0149 (17)	0.0162 (17)	0.0118 (17)	−0.0085 (14)	0.0039 (13)	−0.0025 (13)
C2A	0.0149 (17)	0.0183 (17)	0.0116 (17)	−0.0080 (14)	0.0046 (13)	0.0002 (13)
N3A	0.0147 (14)	0.0143 (14)	0.0125 (14)	−0.0072 (12)	0.0018 (11)	−0.0007 (11)
C3A	0.0164 (17)	0.0149 (17)	0.0143 (17)	−0.0056 (14)	0.0005 (14)	0.0028 (13)
C4A	0.0140 (17)	0.0135 (16)	0.0091 (16)	−0.0045 (14)	0.0004 (13)	0.0030 (13)
C5A	0.0171 (18)	0.0204 (18)	0.0149 (18)	−0.0052 (15)	−0.0005 (14)	0.0013 (14)
C6A	0.0223 (19)	0.0185 (18)	0.0201 (19)	−0.0055 (15)	−0.0017 (15)	−0.0067 (15)
C7A	0.0175 (18)	0.0219 (19)	0.0218 (19)	−0.0103 (15)	−0.0026 (15)	−0.0017 (15)
C8A	0.0140 (17)	0.0130 (16)	0.0138 (17)	−0.0043 (14)	−0.0022 (13)	0.0015 (13)
N4A	0.0173 (15)	0.0122 (14)	0.0128 (14)	−0.0066 (12)	−0.0010 (12)	−0.0004 (11)
C9A	0.0143 (17)	0.0152 (17)	0.0193 (18)	−0.0048 (14)	0.0016 (14)	−0.0003 (14)
N5A	0.0149 (14)	0.0174 (15)	0.0161 (15)	−0.0068 (12)	−0.0002 (12)	0.0011 (12)
C10A	0.0153 (18)	0.0237 (19)	0.0207 (19)	−0.0056 (15)	0.0012 (14)	−0.0010 (15)
C11A	0.0220 (19)	0.0161 (18)	0.0188 (19)	−0.0057 (15)	0.0023 (15)	−0.0015 (14)
N2	0.0160 (14)	0.0146 (14)	0.0149 (15)	−0.0050 (12)	0.0022 (11)	0.0003 (11)
C1B	0.0130 (16)	0.0141 (16)	0.0134 (17)	−0.0057 (14)	0.0042 (13)	−0.0004 (13)
C2B	0.0120 (16)	0.0158 (17)	0.0108 (16)	−0.0037 (14)	0.0040 (13)	−0.0015 (13)
N3B	0.0118 (14)	0.0130 (14)	0.0144 (14)	−0.0039 (11)	0.0038 (11)	−0.0015 (11)
C3B	0.0160 (17)	0.0155 (17)	0.0164 (17)	−0.0064 (14)	0.0026 (14)	−0.0035 (14)
C4B	0.0186 (18)	0.0136 (17)	0.0114 (17)	−0.0076 (14)	0.0010 (13)	0.0034 (13)
C5B	0.0231 (19)	0.0164 (17)	0.0151 (17)	−0.0116 (15)	0.0018 (14)	0.0008 (14)
C6B	0.033 (2)	0.0119 (17)	0.0132 (17)	−0.0105 (15)	0.0023 (15)	−0.0023 (14)
C7B	0.0238 (19)	0.0107 (16)	0.0131 (17)	−0.0025 (14)	0.0052 (14)	−0.0019 (13)
C8B	0.0175 (17)	0.0134 (16)	0.0098 (16)	−0.0047 (14)	0.0020 (13)	0.0022 (13)
N4B	0.0165 (15)	0.0109 (14)	0.0121 (14)	−0.0036 (12)	0.0026 (11)	−0.0008 (11)
C9B	0.0161 (17)	0.0147 (17)	0.0176 (18)	−0.0021 (14)	0.0025 (14)	0.0005 (14)
N5B	0.0122 (14)	0.0161 (15)	0.0257 (17)	−0.0022 (12)	0.0008 (12)	−0.0040 (12)
C10B	0.0144 (17)	0.026 (2)	0.0206 (19)	−0.0058 (15)	0.0033 (14)	−0.0068 (15)
C11B	0.0132 (17)	0.0142 (17)	0.0176 (18)	−0.0045 (14)	0.0039 (14)	0.0000 (14)
C1C	0.0121 (16)	0.0148 (17)	0.0169 (17)	−0.0058 (14)	0.0004 (13)	0.0001 (13)
C2C	0.0153 (17)	0.0148 (17)	0.0145 (17)	−0.0067 (14)	−0.0005 (13)	−0.0010 (13)
N3C	0.0145 (14)	0.0113 (14)	0.0129 (14)	−0.0051 (11)	−0.0013 (11)	0.0017 (11)
C3C	0.0143 (17)	0.0119 (16)	0.0148 (17)	−0.0040 (14)	−0.0002 (13)	0.0031 (13)
C4C	0.0171 (17)	0.0097 (16)	0.0094 (16)	−0.0042 (13)	0.0008 (13)	0.0043 (13)
C5C	0.0210 (18)	0.0118 (17)	0.0161 (17)	−0.0054 (14)	0.0011 (14)	−0.0007 (13)
C6C	0.028 (2)	0.0164 (18)	0.0139 (17)	−0.0108 (15)	−0.0015 (15)	−0.0015 (14)
C7C	0.0214 (18)	0.0172 (18)	0.0184 (18)	−0.0111 (15)	−0.0051 (15)	0.0046 (14)
C8C	0.0176 (17)	0.0159 (17)	0.0102 (16)	−0.0091 (14)	−0.0019 (13)	0.0056 (13)
N4C	0.0195 (15)	0.0110 (14)	0.0093 (14)	−0.0073 (12)	0.0002 (11)	−0.0005 (11)
C9C	0.0148 (17)	0.0186 (18)	0.0152 (17)	−0.0072 (14)	0.0016 (14)	0.0006 (14)
N5C	0.0143 (14)	0.0156 (15)	0.0148 (15)	−0.0052 (12)	0.0022 (11)	0.0009 (11)
C10C	0.0134 (17)	0.0178 (18)	0.0212 (18)	−0.0084 (14)	0.0055 (14)	−0.0033 (14)
C11C	0.0133 (17)	0.0184 (18)	0.0208 (19)	−0.0047 (14)	0.0006 (14)	−0.0015 (14)
Cl1	0.0151 (4)	0.0147 (4)	0.0172 (4)	−0.0063 (3)	0.0035 (3)	−0.0005 (3)
O1A	0.0141 (13)	0.0365 (16)	0.0378 (16)	−0.0076 (12)	0.0066 (11)	0.0126 (13)
O1B	0.0211 (13)	0.0279 (14)	0.0228 (14)	−0.0112 (11)	−0.0034 (11)	0.0019 (11)
O1C	0.0361 (15)	0.0185 (13)	0.0238 (14)	−0.0108 (12)	−0.0062 (12)	−0.0025 (11)
O1D	0.0296 (14)	0.0154 (12)	0.0215 (13)	−0.0114 (11)	0.0061 (11)	−0.0028 (10)
Cl2	0.0172 (4)	0.0126 (4)	0.0151 (4)	−0.0057 (3)	0.0012 (3)	−0.0004 (3)
O2A	0.0369 (16)	0.0300 (15)	0.0313 (15)	−0.0252 (13)	0.0063 (12)	0.0020 (12)
O2B	0.0189 (13)	0.0436 (17)	0.0190 (14)	−0.0043 (12)	−0.0026 (11)	0.0071 (12)
O2C	0.0321 (15)	0.0138 (12)	0.0303 (15)	−0.0104 (11)	−0.0024 (12)	−0.0047 (11)
O2D	0.0301 (14)	0.0169 (13)	0.0172 (13)	−0.0066 (11)	−0.0026 (11)	−0.0022 (10)
Cl3	0.0140 (4)	0.0120 (4)	0.0127 (4)	−0.0055 (3)	0.0007 (3)	0.0014 (3)
O3A	0.0200 (13)	0.0315 (15)	0.0412 (16)	−0.0161 (12)	−0.0119 (12)	0.0140 (12)
O3B	0.0183 (12)	0.0136 (12)	0.0213 (13)	−0.0063 (10)	0.0026 (10)	0.0042 (10)
O3C	0.0278 (14)	0.0136 (12)	0.0175 (13)	−0.0041 (11)	0.0071 (11)	−0.0043 (10)
O3D	0.0304 (14)	0.0234 (13)	0.0129 (12)	−0.0115 (11)	−0.0007 (10)	−0.0005 (10)
Cl4	0.0133 (4)	0.0146 (4)	0.0153 (4)	−0.0052 (3)	0.0031 (3)	−0.0003 (3)
O4A	0.0348 (16)	0.0375 (16)	0.0269 (15)	−0.0193 (13)	−0.0129 (12)	0.0185 (12)
O4B	0.0168 (12)	0.0215 (13)	0.0217 (13)	−0.0087 (10)	0.0030 (10)	−0.0053 (10)
O4C	0.0190 (13)	0.0280 (14)	0.0344 (16)	−0.0072 (11)	0.0125 (11)	−0.0129 (12)
O4D	0.0283 (14)	0.0163 (13)	0.0220 (13)	−0.0110 (11)	0.0012 (11)	0.0019 (10)
Cl5	0.0190 (4)	0.0164 (4)	0.0230 (5)	−0.0087 (3)	0.0004 (3)	0.0054 (3)
O5A	0.0520 (18)	0.0206 (14)	0.0377 (16)	−0.0228 (13)	−0.0085 (14)	0.0025 (12)
O5B	0.0241 (14)	0.0236 (14)	0.0354 (16)	−0.0162 (12)	0.0075 (11)	0.0044 (12)
O5C	0.0444 (18)	0.0394 (17)	0.0256 (15)	−0.0201 (14)	0.0080 (13)	−0.0087 (13)
O5D	0.0214 (15)	0.064 (2)	0.0477 (19)	−0.0124 (15)	−0.0058 (13)	0.0332 (16)
Cl6	0.0143 (4)	0.0189 (4)	0.0148 (4)	−0.0044 (3)	0.0007 (3)	−0.0029 (3)
O6A	0.0203 (13)	0.0271 (14)	0.0254 (14)	−0.0023 (11)	−0.0060 (11)	0.0014 (11)
O6B	0.0265 (14)	0.0325 (15)	0.0291 (15)	−0.0059 (12)	−0.0081 (12)	−0.0108 (12)
O6C	0.0344 (15)	0.0199 (13)	0.0246 (14)	−0.0117 (12)	0.0032 (12)	0.0010 (11)
O6D	0.0231 (14)	0.0414 (16)	0.0206 (14)	−0.0163 (12)	0.0110 (11)	−0.0089 (12)
Cl7	0.0142 (4)	0.0177 (4)	0.0220 (4)	−0.0042 (3)	0.0039 (3)	0.0000 (3)
O7A	0.0184 (13)	0.0275 (14)	0.0294 (15)	−0.0011 (11)	0.0074 (11)	−0.0098 (12)
O7B	0.0338 (16)	0.0480 (18)	0.0293 (16)	−0.0138 (14)	0.0001 (13)	−0.0103 (13)
O7C	0.0314 (16)	0.0285 (15)	0.0370 (17)	−0.0005 (13)	0.0057 (13)	0.0160 (13)
O7D	0.0217 (14)	0.0282 (15)	0.059 (2)	−0.0141 (12)	0.0010 (13)	0.0026 (14)
Cl8	0.0211 (5)	0.0194 (5)	0.0318 (5)	−0.0025 (4)	0.0015 (4)	−0.0002 (4)
O8A	0.076 (3)	0.118 (4)	0.126 (4)	−0.032 (3)	0.033 (3)	−0.101 (4)
O8B	0.088 (3)	0.104 (4)	0.138 (4)	−0.060 (3)	−0.083 (3)	0.076 (3)
O8C	0.074 (3)	0.0227 (17)	0.084 (3)	−0.0122 (17)	0.042 (2)	0.0052 (17)
O8D	0.0226 (17)	0.076 (3)	0.065 (2)	−0.0131 (17)	0.0040 (16)	−0.0039 (19)
O1W	0.0356 (16)	0.0208 (14)	0.0212 (14)	−0.0034 (13)	−0.0045 (12)	−0.0003 (12)
O2W	0.0250 (14)	0.0196 (14)	0.0277 (15)	−0.0106 (12)	−0.0048 (12)	0.0026 (11)
O3W	0.0372 (17)	0.0388 (17)	0.0250 (15)	−0.0190 (14)	−0.0112 (13)	0.0038 (13)
O4W	0.0352 (17)	0.0383 (18)	0.049 (2)	−0.0187 (15)	−0.0029 (15)	−0.0072 (15)
O5W	0.0343 (18)	0.0237 (16)	0.059 (2)	−0.0075 (13)	−0.0003 (15)	−0.0132 (15)

Geometric parameters (Å, º)

N1—C1A	1.469 (4)	C1C—H1C2	0.9900
N1—C1B	1.469 (4)	C2C—N3C	1.488 (4)
N1—C1C	1.469 (4)	C2C—H2C1	0.9900
C1A—C2A	1.514 (5)	C2C—H2C2	0.9900
C1A—H1A1	0.9900	N3C—C3C	1.504 (4)
C1A—H1A2	0.9900	N3C—H3C1	0.9200
C2A—N3A	1.496 (4)	N3C—H3C2	0.9200
C2A—H2A1	0.9900	C3C—C4C	1.500 (5)
C2A—H2A2	0.9900	C3C—H3C3	0.9900
N3A—C3A	1.505 (4)	C3C—H3C4	0.9900
N3A—H3A1	0.9200	C4C—N4C	1.352 (4)
N3A—H3A2	0.9200	C4C—C5C	1.372 (5)
C3A—C4A	1.508 (5)	C5C—C6C	1.382 (5)
C3A—H3A3	0.9900	C5C—H5C	0.9500
C3A—H3A4	0.9900	C6C—C7C	1.397 (5)
C4A—N4A	1.353 (4)	C6C—H6C	0.9500
C4A—C5A	1.366 (5)	C7C—C8C	1.376 (5)
C5A—C6A	1.383 (5)	C7C—H7C	0.9500
C5A—H5A	0.9500	C8C—N4C	1.351 (4)
C6A—C7A	1.394 (5)	C8C—C9C	1.508 (5)
C6A—H6A	0.9500	N4C—H4C	0.82 (4)
C7A—C8A	1.374 (5)	C9C—N5C	1.507 (4)
C7A—H7A	0.9500	C9C—H9C1	0.9900
C8A—N4A	1.351 (4)	C9C—H9C2	0.9900
C8A—C9A	1.512 (4)	N5C—C10C	1.507 (4)
N4A—H4A	0.85 (4)	N5C—H5C1	0.9200
C9A—N5A	1.499 (4)	N5C—H5C2	0.9200
C9A—H9A1	0.9900	C10C—C11C	1.528 (5)
C9A—H9A2	0.9900	C10C—H10E	0.9900
N5A—C10A	1.504 (4)	C10C—H10F	0.9900
N5A—H5A1	0.9200	C11C—H11E	0.9900
N5A—H5A2	0.9200	C11C—H11F	0.9900
C10A—C11A	1.505 (5)	Cl1—O1B	1.431 (3)
C10A—H10A	0.9900	Cl1—O1A	1.442 (3)
C10A—H10B	0.9900	Cl1—O1C	1.444 (3)
C11A—N2	1.482 (4)	Cl1—O1D	1.450 (2)
C11A—H11A	0.9900	Cl2—O2C	1.427 (2)
C11A—H11B	0.9900	Cl2—O2B	1.433 (3)
N2—C11B	1.459 (4)	Cl2—O2A	1.437 (3)
N2—C11C	1.479 (4)	Cl2—O2D	1.456 (2)
C1B—C2B	1.532 (5)	Cl3—O3D	1.423 (2)
C1B—H1B1	0.9900	Cl3—O3A	1.438 (3)
C1B—H1B2	0.9900	Cl3—O3C	1.447 (2)
C2B—N3B	1.500 (4)	Cl3—O3B	1.448 (2)
C2B—H2B1	0.9900	Cl4—O4D	1.434 (2)
C2B—H2B2	0.9900	Cl4—O4C	1.434 (3)
N3B—C3B	1.484 (4)	Cl4—O4A	1.435 (3)
N3B—H3B1	0.9200	Cl4—O4B	1.447 (2)
N3B—H3B2	0.9200	Cl5—O5D	1.424 (3)
C3B—C4B	1.523 (4)	Cl5—O5C	1.426 (3)
C3B—H3B3	0.9900	Cl5—O5A	1.442 (3)
C3B—H3B4	0.9900	Cl5—O5B	1.447 (2)
C4B—N4B	1.339 (4)	Cl6—O6B	1.422 (3)
C4B—C5B	1.383 (5)	Cl6—O6D	1.436 (2)
C5B—C6B	1.382 (5)	Cl6—O6A	1.442 (3)
C5B—H5B	0.9500	Cl6—O6C	1.448 (3)
C6B—C7B	1.387 (5)	Cl7—O7C	1.426 (3)
C6B—H6B	0.9500	Cl7—O7B	1.428 (3)
C7B—C8B	1.385 (5)	Cl7—O7D	1.437 (3)
C7B—H7B	0.9500	Cl7—O7A	1.458 (3)
C8B—N4B	1.346 (4)	Cl8—O8A	1.393 (4)
C8B—C9B	1.506 (5)	Cl8—O8B	1.399 (4)
C9B—N5B	1.491 (4)	Cl8—O8D	1.405 (3)
C9B—H9B1	0.9900	Cl8—O8C	1.423 (3)
C9B—H9B2	0.9900	O1W—H1WA	0.85 (5)
N5B—C10B	1.498 (4)	O1W—H1WB	0.91 (5)
N5B—H5B1	0.9200	O2W—H2WA	0.87 (4)
N5B—H5B2	0.9200	O2W—H2WB	0.81 (4)
C10B—C11B	1.526 (5)	O3W—H3WA	0.82 (5)
C10B—H10C	0.9900	O3W—H3WB	0.90 (5)
C10B—H10D	0.9900	O4W—H4WA	0.92 (5)
C11B—H11C	0.9900	O4W—H4WB	0.79 (5)
C11B—H11D	0.9900	O5W—H5WA	0.84 (5)
C1C—C2C	1.524 (4)	O5W—H5WB	0.87 (5)
C1C—H1C1	0.9900
C1B—N1—C1A	113.6 (2)	C11B—C10B—H10D	109.9
C1B—N1—C1C	114.7 (3)	H10C—C10B—H10D	108.3
C1A—N1—C1C	109.8 (2)	N2—C11B—C10B	115.8 (3)
N1—C1A—C2A	111.0 (3)	N2—C11B—H11C	108.3
N1—C1A—H1A1	109.4	C10B—C11B—H11C	108.3
C2A—C1A—H1A1	109.4	N2—C11B—H11D	108.3
N1—C1A—H1A2	109.4	C10B—C11B—H11D	108.3
C2A—C1A—H1A2	109.4	H11C—C11B—H11D	107.4
H1A1—C1A—H1A2	108.0	N1—C1C—C2C	112.1 (3)
N3A—C2A—C1A	110.2 (3)	N1—C1C—H1C1	109.2
N3A—C2A—H2A1	109.6	C2C—C1C—H1C1	109.2
C1A—C2A—H2A1	109.6	N1—C1C—H1C2	109.2
N3A—C2A—H2A2	109.6	C2C—C1C—H1C2	109.2
C1A—C2A—H2A2	109.6	H1C1—C1C—H1C2	107.9
H2A1—C2A—H2A2	108.1	N3C—C2C—C1C	110.4 (3)
C2A—N3A—C3A	113.1 (2)	N3C—C2C—H2C1	109.6
C2A—N3A—H3A1	109.0	C1C—C2C—H2C1	109.6
C3A—N3A—H3A1	109.0	N3C—C2C—H2C2	109.6
C2A—N3A—H3A2	109.0	C1C—C2C—H2C2	109.6
C3A—N3A—H3A2	109.0	H2C1—C2C—H2C2	108.1
H3A1—N3A—H3A2	107.8	C2C—N3C—C3C	112.0 (2)
N3A—C3A—C4A	111.9 (3)	C2C—N3C—H3C1	109.2
N3A—C3A—H3A3	109.2	C3C—N3C—H3C1	109.2
C4A—C3A—H3A3	109.2	C2C—N3C—H3C2	109.2
N3A—C3A—H3A4	109.2	C3C—N3C—H3C2	109.2
C4A—C3A—H3A4	109.2	H3C1—N3C—H3C2	107.9
H3A3—C3A—H3A4	107.9	C4C—C3C—N3C	109.9 (3)
N4A—C4A—C5A	118.4 (3)	C4C—C3C—H3C3	109.7
N4A—C4A—C3A	117.4 (3)	N3C—C3C—H3C3	109.7
C5A—C4A—C3A	124.2 (3)	C4C—C3C—H3C4	109.7
C4A—C5A—C6A	119.6 (3)	N3C—C3C—H3C4	109.7
C4A—C5A—H5A	120.2	H3C3—C3C—H3C4	108.2
C6A—C5A—H5A	120.2	N4C—C4C—C5C	118.5 (3)
C5A—C6A—C7A	120.5 (3)	N4C—C4C—C3C	117.5 (3)
C5A—C6A—H6A	119.8	C5C—C4C—C3C	124.0 (3)
C7A—C6A—H6A	119.8	C4C—C5C—C6C	120.0 (3)
C8A—C7A—C6A	118.8 (3)	C4C—C5C—H5C	120.0
C8A—C7A—H7A	120.6	C6C—C5C—H5C	120.0
C6A—C7A—H7A	120.6	C5C—C6C—C7C	119.7 (3)
N4A—C8A—C7A	118.8 (3)	C5C—C6C—H6C	120.2
N4A—C8A—C9A	115.1 (3)	C7C—C6C—H6C	120.2
C7A—C8A—C9A	126.1 (3)	C8C—C7C—C6C	119.7 (3)
C8A—N4A—C4A	123.8 (3)	C8C—C7C—H7C	120.2
C8A—N4A—H4A	119 (2)	C6C—C7C—H7C	120.2
C4A—N4A—H4A	117 (2)	N4C—C8C—C7C	118.2 (3)
N5A—C9A—C8A	112.3 (3)	N4C—C8C—C9C	116.9 (3)
N5A—C9A—H9A1	109.1	C7C—C8C—C9C	124.9 (3)
C8A—C9A—H9A1	109.1	C8C—N4C—C4C	124.0 (3)
N5A—C9A—H9A2	109.1	C8C—N4C—H4C	118 (3)
C8A—C9A—H9A2	109.1	C4C—N4C—H4C	118 (3)
H9A1—C9A—H9A2	107.9	N5C—C9C—C8C	111.8 (3)
C9A—N5A—C10A	114.3 (3)	N5C—C9C—H9C1	109.2
C9A—N5A—H5A1	108.7	C8C—C9C—H9C1	109.2
C10A—N5A—H5A1	108.7	N5C—C9C—H9C2	109.2
C9A—N5A—H5A2	108.7	C8C—C9C—H9C2	109.2
C10A—N5A—H5A2	108.7	H9C1—C9C—H9C2	107.9
H5A1—N5A—H5A2	107.6	C10C—N5C—C9C	111.2 (2)
N5A—C10A—C11A	113.1 (3)	C10C—N5C—H5C1	109.4
N5A—C10A—H10A	109.0	C9C—N5C—H5C1	109.4
C11A—C10A—H10A	109.0	C10C—N5C—H5C2	109.4
N5A—C10A—H10B	109.0	C9C—N5C—H5C2	109.4
C11A—C10A—H10B	109.0	H5C1—N5C—H5C2	108.0
H10A—C10A—H10B	107.8	N5C—C10C—C11C	112.3 (3)
N2—C11A—C10A	114.1 (3)	N5C—C10C—H10E	109.2
N2—C11A—H11A	108.7	C11C—C10C—H10E	109.2
C10A—C11A—H11A	108.7	N5C—C10C—H10F	109.2
N2—C11A—H11B	108.7	C11C—C10C—H10F	109.2
C10A—C11A—H11B	108.7	H10E—C10C—H10F	107.9
H11A—C11A—H11B	107.6	N2—C11C—C10C	114.1 (3)
C11B—N2—C11C	115.3 (3)	N2—C11C—H11E	108.7
C11B—N2—C11A	110.6 (3)	C10C—C11C—H11E	108.7
C11C—N2—C11A	112.2 (3)	N2—C11C—H11F	108.7
N1—C1B—C2B	117.4 (3)	C10C—C11C—H11F	108.7
N1—C1B—H1B1	107.9	H11E—C11C—H11F	107.6
C2B—C1B—H1B1	107.9	O1B—Cl1—O1A	110.40 (15)
N1—C1B—H1B2	107.9	O1B—Cl1—O1C	110.06 (15)
C2B—C1B—H1B2	107.9	O1A—Cl1—O1C	109.44 (17)
H1B1—C1B—H1B2	107.2	O1B—Cl1—O1D	109.86 (15)
N3B—C2B—C1B	105.1 (2)	O1A—Cl1—O1D	109.34 (15)
N3B—C2B—H2B1	110.7	O1C—Cl1—O1D	107.69 (14)
C1B—C2B—H2B1	110.7	O2C—Cl2—O2B	110.35 (17)
N3B—C2B—H2B2	110.7	O2C—Cl2—O2A	110.75 (16)
C1B—C2B—H2B2	110.7	O2B—Cl2—O2A	109.33 (17)
H2B1—C2B—H2B2	108.8	O2C—Cl2—O2D	108.66 (15)
C3B—N3B—C2B	116.8 (2)	O2B—Cl2—O2D	108.67 (15)
C3B—N3B—H3B1	108.1	O2A—Cl2—O2D	109.03 (16)
C2B—N3B—H3B1	108.1	O3D—Cl3—O3A	110.87 (15)
C3B—N3B—H3B2	108.1	O3D—Cl3—O3C	109.84 (15)
C2B—N3B—H3B2	108.1	O3A—Cl3—O3C	108.16 (16)
H3B1—N3B—H3B2	107.3	O3D—Cl3—O3B	109.31 (15)
N3B—C3B—C4B	109.0 (3)	O3A—Cl3—O3B	109.39 (14)
N3B—C3B—H3B3	109.9	O3C—Cl3—O3B	109.23 (14)
C4B—C3B—H3B3	109.9	O4D—Cl4—O4C	108.81 (15)
N3B—C3B—H3B4	109.9	O4D—Cl4—O4A	109.45 (16)
C4B—C3B—H3B4	109.9	O4C—Cl4—O4A	111.76 (17)
H3B3—C3B—H3B4	108.3	O4D—Cl4—O4B	109.79 (15)
N4B—C4B—C5B	123.2 (3)	O4C—Cl4—O4B	108.46 (15)
N4B—C4B—C3B	115.5 (3)	O4A—Cl4—O4B	108.56 (15)
C5B—C4B—C3B	121.2 (3)	O5D—Cl5—O5C	111.70 (19)
C6B—C5B—C4B	118.5 (3)	O5D—Cl5—O5A	108.8 (2)
C6B—C5B—H5B	120.8	O5C—Cl5—O5A	108.56 (17)
C4B—C5B—H5B	120.8	O5D—Cl5—O5B	109.78 (17)
C5B—C6B—C7B	119.3 (3)	O5C—Cl5—O5B	110.13 (17)
C5B—C6B—H6B	120.3	O5A—Cl5—O5B	107.72 (16)
C7B—C6B—H6B	120.3	O6B—Cl6—O6D	111.04 (16)
C8B—C7B—C6B	118.4 (3)	O6B—Cl6—O6A	109.55 (16)
C8B—C7B—H7B	120.8	O6D—Cl6—O6A	109.73 (16)
C6B—C7B—H7B	120.8	O6B—Cl6—O6C	109.43 (17)
N4B—C8B—C7B	122.9 (3)	O6D—Cl6—O6C	109.19 (16)
N4B—C8B—C9B	115.4 (3)	O6A—Cl6—O6C	107.84 (16)
C7B—C8B—C9B	121.6 (3)	O7C—Cl7—O7B	110.16 (19)
C4B—N4B—C8B	117.6 (3)	O7C—Cl7—O7D	110.31 (18)
N5B—C9B—C8B	110.0 (3)	O7B—Cl7—O7D	108.83 (18)
N5B—C9B—H9B1	109.7	O7C—Cl7—O7A	109.70 (16)
C8B—C9B—H9B1	109.7	O7B—Cl7—O7A	108.61 (17)
N5B—C9B—H9B2	109.7	O7D—Cl7—O7A	109.20 (16)
C8B—C9B—H9B2	109.7	O8A—Cl8—O8B	109.5 (4)
H9B1—C9B—H9B2	108.2	O8A—Cl8—O8D	111.8 (3)
C9B—N5B—C10B	114.3 (3)	O8B—Cl8—O8D	110.2 (3)
C9B—N5B—H5B1	108.7	O8A—Cl8—O8C	108.7 (3)
C10B—N5B—H5B1	108.7	O8B—Cl8—O8C	106.0 (3)
C9B—N5B—H5B2	108.7	O8D—Cl8—O8C	110.5 (2)
C10B—N5B—H5B2	108.7	H1WA—O1W—H1WB	127 (4)
H5B1—N5B—H5B2	107.6	H2WA—O2W—H2WB	103 (4)
N5B—C10B—C11B	108.8 (3)	H3WA—O3W—H3WB	102 (4)
N5B—C10B—H10C	109.9	H4WA—O4W—H4WB	117 (5)
C11B—C10B—H10C	109.9	H5WA—O5W—H5WB	105 (5)
N5B—C10B—H10D	109.9
C1B—N1—C1A—C2A	−60.2 (3)	C6B—C7B—C8B—C9B	−177.8 (3)
C1C—N1—C1A—C2A	169.9 (3)	C5B—C4B—N4B—C8B	−0.6 (5)
N1—C1A—C2A—N3A	−175.5 (2)	C3B—C4B—N4B—C8B	−177.6 (3)
C1A—C2A—N3A—C3A	−175.5 (3)	C7B—C8B—N4B—C4B	0.0 (5)
C2A—N3A—C3A—C4A	−54.6 (3)	C9B—C8B—N4B—C4B	178.2 (3)
N3A—C3A—C4A—N4A	106.1 (3)	N4B—C8B—C9B—N5B	35.2 (4)
N3A—C3A—C4A—C5A	−72.3 (4)	C7B—C8B—C9B—N5B	−146.6 (3)
N4A—C4A—C5A—C6A	−1.7 (5)	C8B—C9B—N5B—C10B	−173.0 (3)
C3A—C4A—C5A—C6A	176.7 (3)	C9B—N5B—C10B—C11B	145.1 (3)
C4A—C5A—C6A—C7A	1.8 (5)	C11C—N2—C11B—C10B	−76.8 (4)
C5A—C6A—C7A—C8A	0.3 (5)	C11A—N2—C11B—C10B	51.9 (4)
C6A—C7A—C8A—N4A	−2.3 (5)	N5B—C10B—C11B—N2	−171.2 (3)
C6A—C7A—C8A—C9A	176.6 (3)	C1B—N1—C1C—C2C	64.3 (3)
C7A—C8A—N4A—C4A	2.5 (5)	C1A—N1—C1C—C2C	−166.3 (3)
C9A—C8A—N4A—C4A	−176.5 (3)	N1—C1C—C2C—N3C	45.4 (4)
C5A—C4A—N4A—C8A	−0.5 (5)	C1C—C2C—N3C—C3C	168.5 (3)
C3A—C4A—N4A—C8A	−178.9 (3)	C2C—N3C—C3C—C4C	173.5 (3)
N4A—C8A—C9A—N5A	−151.6 (3)	N3C—C3C—C4C—N4C	−85.5 (3)
C7A—C8A—C9A—N5A	29.4 (5)	N3C—C3C—C4C—C5C	92.8 (4)
C8A—C9A—N5A—C10A	−178.4 (3)	N4C—C4C—C5C—C6C	0.6 (5)
C9A—N5A—C10A—C11A	−66.8 (4)	C3C—C4C—C5C—C6C	−177.7 (3)
N5A—C10A—C11A—N2	−61.9 (4)	C4C—C5C—C6C—C7C	0.0 (5)
C10A—C11A—N2—C11B	144.9 (3)	C5C—C6C—C7C—C8C	0.1 (5)
C10A—C11A—N2—C11C	−84.8 (3)	C6C—C7C—C8C—N4C	−0.8 (5)
C1A—N1—C1B—C2B	−55.2 (4)	C6C—C7C—C8C—C9C	−178.8 (3)
C1C—N1—C1B—C2B	72.3 (3)	C7C—C8C—N4C—C4C	1.5 (5)
N1—C1B—C2B—N3B	179.2 (3)	C9C—C8C—N4C—C4C	179.7 (3)
C1B—C2B—N3B—C3B	−177.5 (3)	C5C—C4C—N4C—C8C	−1.4 (5)
C2B—N3B—C3B—C4B	164.1 (3)	C3C—C4C—N4C—C8C	177.0 (3)
N3B—C3B—C4B—N4B	−14.1 (4)	N4C—C8C—C9C—N5C	93.5 (3)
N3B—C3B—C4B—C5B	168.8 (3)	C7C—C8C—C9C—N5C	−88.5 (4)
N4B—C4B—C5B—C6B	0.9 (5)	C8C—C9C—N5C—C10C	−171.5 (3)
C3B—C4B—C5B—C6B	177.7 (3)	C9C—N5C—C10C—C11C	−172.6 (3)
C4B—C5B—C6B—C7B	−0.7 (5)	C11B—N2—C11C—C10C	−52.4 (4)
C5B—C6B—C7B—C8B	0.1 (5)	C11A—N2—C11C—C10C	179.7 (3)
C6B—C7B—C8B—N4B	0.2 (5)	N5C—C10C—C11C—N2	−52.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A1···O1D	0.92	1.93	2.850 (4)	173
N3A—H3A2···O5A^i	0.92	2.11	2.889 (4)	142
N4A—H4A···O2D	0.85 (4)	1.91 (4)	2.755 (4)	173 (4)
N5A—H5A1···O4B	0.92	2.01	2.914 (4)	167
N5A—H5A2···O2W	0.92	1.99	2.798 (4)	146
N5A—H5A2···O1C^ii	0.92	2.51	2.987 (4)	113
N3B—H3B1···O2B	0.92	2.16	2.829 (4)	129
N3B—H3B2···O6A	0.92	2.15	2.850 (4)	132
N3B—H3B2···O3B	0.92	2.32	2.974 (3)	128
N5B—H5B1···O7A	0.92	1.98	2.874 (4)	162
N5B—H5B2···O2A	0.92	2.42	2.998 (4)	121
N5B—H5B2···O3B	0.92	2.45	2.976 (4)	117
N3C—H3C1···O1W	0.92	1.81	2.672 (4)	155
N3C—H3C1···O8D	0.92	2.56	3.114 (4)	119
N3C—H3C2···O4A	0.92	2.29	3.121 (4)	150
N3C—H3C2···O3C	0.92	2.43	2.956 (4)	116
N4C—H4C···O3C	0.82 (4)	2.29 (4)	2.991 (4)	145 (3)
N5C—H5C1···O4A	0.92	2.33	3.168 (4)	152
N5C—H5C1···O4B	0.92	2.60	3.125 (4)	116
N5C—H5C2···O3W	0.92	1.76	2.661 (4)	165
O1W—H1WA···O4C	0.85 (5)	2.06 (5)	2.833 (4)	151 (4)
O1W—H1WA···O1A	0.85 (5)	2.39 (4)	2.992 (4)	129 (4)
O1W—H1WB···O2W^ii	0.91 (5)	2.03 (5)	2.840 (4)	147 (4)
O2W—H2WA···O5B	0.87 (4)	1.92 (5)	2.781 (4)	167 (4)
O2W—H2WB···O1B^ii	0.81 (4)	2.51 (4)	2.927 (4)	113 (3)
O2W—H2WB···O5A^iii	0.81 (4)	2.62 (4)	3.281 (4)	140 (4)
O3W—H3WA···O1C^ii	0.82 (5)	2.14 (5)	2.924 (4)	160 (4)
O3W—H3WA···O1D^ii	0.82 (5)	2.61 (5)	3.237 (4)	135 (4)
O3W—H3WB···O4W	0.90 (5)	1.83 (5)	2.667 (4)	155 (4)
O4W—H4WA···O5W^iv	0.92 (5)	1.89 (5)	2.746 (5)	155 (4)
O4W—H4WB···O8B^v	0.79 (5)	2.39 (5)	3.127 (6)	155 (5)
O4W—H4WB···O8C^v	0.79 (5)	2.51 (5)	3.218 (6)	149 (5)
O5W—H5WA···O6C^vi	0.84 (5)	2.04 (5)	2.871 (4)	171 (5)
O5W—H5WB···O7D	0.87 (5)	2.00 (5)	2.846 (4)	161 (5)

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