Bis(2-amino-1H-benzimidazol-3-ium) tetra­kis­(μ-but-2-en­oato)-κ⁴O:O′;κ³O,O′:O;κ³O:O,O′-bis­[bis­(but-2-en­oato-κ²O,O′)holmium(III)]

The title ionic compound, (C₇H₈N₃)₂[Ho₂(C₄H₅O₂)₈], is con­structed from two almost identical independent centrosymmetric anionic dimers balanced by two independent 2-amino-1H-benzimid­azol-3-ium (Habim⁺) cations. The asymmetric part of each dimer is made up of one Ho^III cation and four crotonate (crot or but-2-enoate) anions, two of them acting in a simple η²-chelating mode and the remaining two acting in two different μ₂:η² fashions, viz. purely bridging and bridging–chelating. Symmetry-related Ho^III cations are linked by two Ho—O—Ho and two Ho—O—C—O—Ho bridges which lead to rather short intra­cationic Ho...Ho distances [3.8418 (3) and 3.8246 (3) Å]. In addition to the obvious Coulombic inter­actions linking the cations and anions, the isolated [Ho₂(crot)₈]²⁻ and Habim⁺ ions are linked by a number of N—H...O hydrogen bonds, in which all N—H groups of the cation are involved as donors and all (simple chelating) crot O atoms are involved as acceptors. These inter­actions result in compact two-dimensional structures parallel to (110), which are linked to each other by weaker π–π contacts between Habim⁺ benzene groups.

S1. Comment

Carboxylate-bridged homonuclear systems constitute a popular target in structural chemistry, mainly due to the coordination versatility which these ligands introduce. This allows for a diversity of frameworks of varied complexity and dimensionality, from simple zero-dimensional isolated dimeric units up to tightly bound three-dimensional structures, correlating with a concomitant diversity in physical properties, leading to applications in fields as diverse as ion exchange, catalysis, molecular absorption, optics, electronics etc. (Ma et al., 2000; Wang et al., 2002; Xu et al., 2002; Benelli & Gatteschi, 2002; Pan et al., 2004).

We have for some time focused our attention on the efficiency of crotonic acid (C₃H₅COOH, hereinafter denoted Hcrot; systematic name: but-2-enoic acid) in coupling Ln^III ions, and as a result we have described the synthesis and structural and (eventually) magnetic characterization of a number of crotoate–lanthanide complexes obtained in conjuntion with a variety of nitrogenous bases (NB), such as diaminopurine, adenine etc., which proved quite efficient in promoting crystal stabilization, either through their inclusion as neutral cocrystallization agents (Atria et al. 2009, 2012a,b), as counter-ions (Atria, Morel et al., 2011) or even as coordinating ligands (Atria, Corsini et al., 2011; Atria, Garland & Baggio, 2011).

In pursuit of our synthetic efforts in this line, we succeeded in generating a new member of the Ln–crot–NB family, this time with Ln = Ho and NB = 2-amino-1H-benzimidazol-3-ium (hereinafter Habim⁺), and which we present herein: the dinuclear ionic complex formulated as (Habim)₂[Ho₂(crot)₈], (I). The compound consists of two almost identical centrosymmetric [Ho₂(crot)₈]^2- anionic dimers complemented by two independent Habim⁺ cations, providing for charge balance and structural cohesion. These four different groups in the structure associate in two similar cation–anion pairs which we differentiate with the suffixes A and B (as shown in Fig. 1). To facilitate comparison, equivalent atoms in different groups have been given the same number.

Each independent `half-dimer', A or B in Fig. 1, is made up of one Ho^III cation and four crot anions, two of which act in a simple η²-chelating mode (crot1 and crot2), while the remaining two bind in two different µ₂η² fashions, viz. purely bridging (crot4) and bridging–chelating (crot3). The distribution of Ho—O distances is rather similar in both dimeric units, displaying ranges of 2.290 (2)–2.523 (2)/2.305 (2)–2.531 (2) Å [in what follows, values separated by a solidus (/) are presented in A/B order]. Selected coordination details are given in Table 1.

The insets in Fig. 1 show the very similar HoO₉ coordination assemblies, which consist of five O atoms in equatorial positions and which describe a rather planar structure [mean deviations 0.043 (2)/0.025 (2) Å], capped by one O atom above the plane and a triangular array on the opposite side. The Ho^III cation, in turn, lies 0.535 (2)/0.539 (2) Å below the pentagonal equatorial mean plane.

Although four isolated Ln(RCOO)₈ nuclei of this kind having different Ln centres have been reported in the literature [Cambridge Structural Database (CSD; Allen, 2002) refcodes EXUXIE (Ln = Eu), CUMTOU (Ln = La), VUJPEV (Ln = Gd) [Full references needed for these three refcodes] and RAPCOB (Ln = Lu; Li & Hu, 2005)], none of them features Ho^III as the cation, making (I) the first complex to display such an Ho(RCOO)₈ nucleus. Nonetheless, there are structures with similar bridging schemes around Ho centres (viz. two pairs of Ho—O—Ho and Ho—O—C—O—Ho bridges), which in the present case lead to Ho···Ho distances of 3.8418 (3)/3.8246 (3) Å, at the lower limit of the range reported for Ho···Ho distances in this particular bridging configuration. A search of the CSD retrieved 14 structures of this type with Ho···Ho distances in the range 3.8559 (9) Å (CSD refcode NADBIF; Guo et al., 2010) to 4.2422 (15) Å (CSD refcode PUKFUW; Legendziewicz et al., 1989). Therefore, none exhibits a shorter Ho···Ho distance than those herein reported.

As stated above, the dimeric units A and B are extremely similar, not only in their metrics (Table 1) but also in some particular geometric details. Each one presents four well-defined coordination planes, 1–4, and these are presented in Table 2 with their maximum deviations from planarity. The most conspicuous plane is 1, shown as a shaded area in Fig. 1; it halves each dimeric unit, acting as a `basal' plane, with the remaining three planes (2–4) disposed very nearly perpendicular to it, subtending dihedral angles which differ from the ideal 90° by less than 4.1 (2)/2.5 (2)°.

The unbound protonated Habim⁺ counter-anions do not show any unexpected features. This form of the aminobenzimidazole unit, present in (I), is frequently adopted by the molecule in the solid state: out of 25 structures found in the CSD containing the moiety in any of its forms, in 11 it appears protonated, while in 12 it behaves as a coordinated ligand, either through both imidazole N atoms (three entries) or simply through one of them (nine entries). Only in two structures does aminobenzimidazole appear as a neutral uncoordinated species [CSD refcodes DIQLEU (Wulff-Molder & Meisel, 1999) and HUZSEA (El-Medani et al., 2003)].

The crystal packing in (I) involves a mixture of different interactions of varied type and strength. In addition to the obvious Coulombic forces between cations and anions, the isolated [Ho₂(crot)₈]^2- and Habim⁺ groups are linked by a number of N—H···O hydrogen bonds, in which all eight Habim⁺ N—H groups are involved as donors and all eight crot O atoms corresponding to the purely chelating carboxylates act as acceptors (Table 3). Each Habim⁺ cation (either A or B) links two dimers of a different (B,A) kind, with two hydrogen bonds at each side. These N—H···O hydrogen bonds are particularly even in both disposition and strength [N···O = 2.722 (4)–2.889 (4) Å], and define compact two-dimensional structures parallel to (110) (Fig. 2). The regularity of the hydrogen-bonding scheme is revealed by the loop structure it gives rise to, defined by four identical R₂²(8) rings (Bernstein et al., 1995) of general scheme ···O—Ho—O···H—N—C—N—H···. When viewed in projection, these structures show an exactly planar core of dimeric centroids [with inversion centres of general coordinates r(n1,n2) = (1/2, 0, 0) + n1(1/2, -1/2, -1/2) + n2(1/2, -1/2, 1/2), where n1 and n2 are integers], while the Habim⁺ cations stretch outwards on both sides and interdigitate with similar ones in adjacent planes, giving raise to π–π contacts between phenyl groups which connect the planes along [110] (Table 4).

Bond valence (BV) analysis using the recently revised coefficients R_ij from Trzesowska et al. (2004) led to BV sums of 3.045 (Ho1A) and 2.979 (Ho1B), consistent with the Ho^III oxidation state of the cations. Similar results were obtained for three of the closely related isocoordinated Ln(RCOO)₈ structures mentioned above (Ln = La, Er and Gd). However, a rather puzzling result was provided by comparison with the fourth compound of the series with Ln = Lu [CSD refcode RAPCOB, (II); Li & Hu, 2005], where the core around the Lu^III cation, very similar to that around the Ho^III centres in (I), is built up by 2-hydroxyphenylacrylate groups. These differ from crot only in that the terminal methyl group in the latter is replaced by a phenyl ring, so we expected similar cation behaviour. However, BV calculations gave an extremely low BV sum of 2.371 for Lu in (II), suggesting much lower involvement of the Lu^III cation in coordination than was found for Ho^III in (I). A possible reason for this intriguing effect is the fact that the terminal groups are quite different electronically, methyl groups being electron-releasing while phenyl rings are, in contrast, electron-withdrawing.

Related literature

For related literature, see: Allen (2002); Atria et al. (2009, 2012a, 2012b); Atria, Corsini, Herrera, Garland & Baggio (2011); Atria, Garland & Baggio (2011); Atria, Morel, Garland & Baggio (2011); Benelli & Gatteschi (2002); Bernstein et al. (1995); El-Medani, Youssef & Ramadan (2003); Guo et al. (2010); Legendziewicz et al. (1989); Li & Hu (2005); Ma et al. (2000); Pan et al. (2004); Trzesowska et al. (2004); Wang et al. (2002); Wulff-Molder & Meisel (1999); Xu et al. (2002).

S2. Experimental

Crotonic acid (0.5165 g, 6 mmol) dissolved in water (30 ml) was added to a solution of Ho₂O₃ (0.3778 g, 1 mmol) in water (300 ml). The resulting solution was refluxed for 30 min. A suspension of 2-aminobenzimidazole (0.1332 g, 1 mmol) in ethanol (30 ml) was added to this solution. The resulting mixture was refluxed for 24 h, filtered and left to evaporate slowly at room temperature. Crystals suitable for structural analysis were obtained after three weeks.

S3. Refinement

All H atoms were originally found in a difference Fourier map, but were treated differently in the refinement. C-bound H atoms were repositioned in their expected positions and thereafter allowed to ride [aromatic C—H = 0.95 Å and methyl C—H = 0.98 Å], while N-bound H atoms were refined with restrained distances of N—H = 0.88 (1) Å and H···H = 1.40 (2) Å. In all cases, U_iso(H) = 1.2U_eq(C,N) or 1.5U_eq(methyl C). In the final difference map, the highest peak lies 1.24 Å from atom Ho1B and the deepest hole 0.92 Å from the same atom. Competitive refinements with the metals set to be Dy or Er gave results which were indistinguishable from those with the metals as Ho.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures

	Fig. 1. The structure of (I), grouped into cation–anion pairs A and B. For clarity, the suffixes A and B are not explicitly shown in the labels, but are defined as part of each figure. Independent (symmetry-related) atoms are shown with solid (hollow) bonds and filled (empty) displacement ellipsoids, drawn at the 40% probability level. Insets: the coordination assembly of the Ho^III cation in each group, where solid (hollow) balls and sticks represent different height levels. [Symmetry codes: (i) -x + 1, -y, -z + 2; (ii) -x, -y + 1, -z + 1.]
	Fig. 2. A packing view of (I), showing the hydrogen-bonded two-dimensional structure. Each [Ho2(crot)8]^2- + Habim^+ group is identified by its A or B suffix. For clarity, crot groups are represented by their carboxylate end only. H atoms attached to C atoms have been omitted.
	Fig. 3. A packing view of (I), drawn along [001], showing the planes in projection. Note the interdigitation of neighbouring Habim^+ cations, linking vicinal planes through π–π contacts. A and B coding is as in Fig. 2.

Bis(2-amino-1H-benzimidazol-3-ium) tetrakis(µ-but-2-enoato)- κ⁴O:O';κ³O,O':O; κ³O:O,O'-bis[bis(but-2-enoato- κ²O,O')holmium(III)]

Crystal data

(C7H8N3)2[Ho2(C4H5O2)8]	Z = 2
Mr = 1278.83	F(000) = 1272
Triclinic, P1	Dx = 1.619 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 14.2688 (8) Å	Cell parameters from 9277 reflections
b = 15.0608 (9) Å	θ = 2.6–27.7°
c = 15.7276 (9) Å	µ = 3.06 mm^−1
α = 66.226 (1)°	T = 150 K
β = 63.654 (1)°	Plate, colourless
γ = 63.700 (1)°	0.26 × 0.13 × 0.05 mm
V = 2624.0 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	11159 independent reflections
Radiation source: sealed tube	9348 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
CCD rotation images, thin slices scans	θmax = 27.8°, θmin = 1.6°
Absorption correction: multi-scan (SADABS in SAINT-NT; Bruker, 2002)	h = −17→18
Tmin = 0.60, Tmax = 0.86	k = −19→19
21803 measured reflections	l = −20→20

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0337P)^2 + 1.0734P] where P = (Fo^2 + 2Fc^2)/3
11159 reflections	(Δ/σ)max = 0.002
663 parameters	Δρmax = 1.97 e Å^−3
10 restraints	Δρmin = −0.59 e Å^−3

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

	x	y	z	Uiso*/Ueq
Ho1A	0.399729 (12)	0.136700 (11)	0.973058 (11)	0.01890 (5)
Ho1B	0.096406 (13)	0.364906 (11)	0.488785 (11)	0.02044 (5)
O11A	0.2594 (2)	0.18171 (19)	1.12332 (18)	0.0275 (6)
O21A	0.2004 (2)	0.15729 (19)	1.03010 (18)	0.0287 (6)
C11A	0.1843 (3)	0.1720 (3)	1.1096 (3)	0.0248 (8)
C21A	0.0786 (3)	0.1699 (3)	1.1913 (3)	0.0330 (9)
H21A	0.0204	0.1686	1.1783	0.040*
C31A	0.0618 (3)	0.1699 (3)	1.2811 (3)	0.0311 (8)
H31A	0.1178	0.1792	1.2905	0.037*
C41A	−0.0368 (4)	0.1566 (3)	1.3691 (3)	0.0446 (11)
H41A	−0.0947	0.1614	1.3484	0.067*
H41B	−0.0645	0.2103	1.4024	0.067*
H41C	−0.0159	0.0893	1.4142	0.067*
O12A	0.3254 (2)	0.26819 (18)	0.84197 (18)	0.0287 (6)
O22A	0.3415 (2)	0.32270 (18)	0.94316 (18)	0.0291 (6)
C12A	0.3116 (3)	0.3411 (3)	0.8713 (3)	0.0254 (8)
C22A	0.2594 (3)	0.4487 (3)	0.8239 (3)	0.0332 (9)
H22A	0.2506	0.5006	0.8492	0.040*
C32A	0.2246 (4)	0.4779 (3)	0.7500 (3)	0.0447 (11)
H32A	0.2377	0.4258	0.7229	0.054*
C42A	0.1657 (4)	0.5859 (3)	0.7035 (4)	0.0586 (14)
H42A	0.1004	0.5875	0.6958	0.088*
H42B	0.2155	0.6102	0.6389	0.088*
H42C	0.1428	0.6303	0.7454	0.088*
O13A	0.59627 (19)	0.02226 (17)	0.91662 (17)	0.0230 (5)
O23A	0.5545 (2)	0.18761 (18)	0.84964 (18)	0.0286 (6)
C13A	0.6254 (3)	0.1020 (3)	0.8631 (2)	0.0219 (7)
C23A	0.7442 (3)	0.0905 (3)	0.8208 (3)	0.0308 (8)
H23A	0.7957	0.0233	0.8298	0.037*
C33A	0.7824 (3)	0.1679 (3)	0.7715 (3)	0.0322 (9)
H33A	0.7294	0.2342	0.7610	0.039*
C43A	0.8998 (4)	0.1625 (4)	0.7306 (4)	0.0547 (13)
H43A	0.9462	0.0910	0.7471	0.082*
H43B	0.9105	0.2035	0.7585	0.082*
H43C	0.9203	0.1892	0.6590	0.082*
O14A	0.40809 (19)	0.04252 (17)	0.88479 (17)	0.0241 (5)
O24A	0.5069 (2)	−0.12309 (18)	0.93096 (17)	0.0242 (5)
C14A	0.4586 (3)	−0.0474 (3)	0.8742 (2)	0.0214 (7)
C24A	0.4635 (3)	−0.0673 (3)	0.7867 (3)	0.0278 (8)
H24A	0.4869	−0.1361	0.7840	0.033*
C34A	0.4365 (3)	0.0076 (3)	0.7133 (3)	0.0340 (9)
H34A	0.4085	0.0755	0.7197	0.041*
C44A	0.4466 (4)	−0.0057 (4)	0.6191 (3)	0.0549 (13)
H44A	0.4940	0.0319	0.5633	0.082*
H44B	0.3732	0.0210	0.6125	0.082*
H44C	0.4792	−0.0787	0.6205	0.082*
O11B	0.2582 (2)	0.3026 (2)	0.54483 (19)	0.0343 (6)
O21B	0.2881 (2)	0.3569 (2)	0.38672 (18)	0.0309 (6)
C11B	0.3237 (3)	0.3175 (3)	0.4585 (3)	0.0265 (8)
C21B	0.4427 (3)	0.2901 (3)	0.4421 (3)	0.0374 (10)
H21B	0.4667	0.2621	0.4977	0.045*
C31B	0.5163 (4)	0.3026 (4)	0.3545 (4)	0.0542 (13)
H31B	0.4899	0.3308	0.3003	0.065*
C41B	0.6371 (4)	0.2771 (5)	0.3313 (4)	0.097 (3)
H41D	0.6551	0.2465	0.3924	0.146*
H41E	0.6574	0.3397	0.2957	0.146*
H41F	0.6781	0.2283	0.2905	0.146*
O12B	0.1769 (2)	0.22778 (19)	0.40900 (18)	0.0314 (6)
O22B	0.1387 (2)	0.17883 (18)	0.56866 (18)	0.0284 (6)
C12B	0.1769 (3)	0.1571 (3)	0.4874 (3)	0.0243 (7)
C22B	0.2191 (3)	0.0486 (3)	0.4847 (3)	0.0328 (9)
H22B	0.2088	−0.0021	0.5453	0.039*
C32B	0.2703 (3)	0.0186 (3)	0.4026 (3)	0.0345 (9)
H32B	0.2809	0.0702	0.3427	0.041*
C42B	0.3128 (4)	−0.0892 (3)	0.3955 (4)	0.0503 (12)
H42D	0.3910	−0.1061	0.3555	0.075*
H42E	0.2707	−0.0964	0.3650	0.075*
H42F	0.3047	−0.1359	0.4614	0.075*
O13B	−0.10133 (19)	0.48281 (18)	0.51447 (17)	0.0242 (5)
O23B	−0.0610 (2)	0.32667 (18)	0.50899 (19)	0.0284 (6)
C13B	−0.1320 (3)	0.4103 (3)	0.5247 (2)	0.0233 (7)
C23B	−0.2511 (3)	0.4257 (3)	0.5582 (3)	0.0344 (9)
H23B	−0.3013	0.4905	0.5693	0.041*
C33B	−0.2925 (3)	0.3554 (3)	0.5739 (3)	0.0358 (9)
H33B	−0.2415	0.2915	0.5613	0.043*
C43B	−0.4129 (4)	0.3676 (4)	0.6099 (4)	0.0539 (13)
H43D	−0.4570	0.4367	0.6190	0.081*
H43E	−0.4303	0.3169	0.6726	0.081*
H43F	−0.4301	0.3571	0.5616	0.081*
O14B	0.0784 (2)	0.46820 (18)	0.33793 (17)	0.0255 (5)
O24B	−0.0139 (2)	0.63130 (18)	0.34834 (17)	0.0260 (5)
C14B	0.0354 (3)	0.5620 (3)	0.3025 (2)	0.0229 (7)
C24B	0.0401 (3)	0.5982 (3)	0.1979 (3)	0.0300 (8)
H24B	0.0285	0.6691	0.1661	0.036*
C34B	0.0595 (3)	0.5370 (3)	0.1472 (3)	0.0380 (10)
H34B	0.0784	0.4654	0.1770	0.046*
C44B	0.0536 (4)	0.5737 (5)	0.0451 (3)	0.0656 (16)
H44D	0.0352	0.6485	0.0230	0.098*
H44E	−0.0034	0.5544	0.0450	0.098*
H44F	0.1252	0.5423	0.0007	0.098*
N1A	0.1621 (3)	0.1060 (2)	0.7551 (2)	0.0288 (7)
H1AA	0.155 (3)	0.124 (3)	0.6975 (14)	0.035*
N2A	0.1754 (3)	0.1010 (3)	0.8907 (2)	0.0300 (7)
H2AA	0.190 (3)	0.120 (3)	0.929 (2)	0.036*
N3A	0.2134 (3)	0.2366 (3)	0.7528 (2)	0.0330 (7)
H3A1	0.248 (3)	0.252 (3)	0.776 (2)	0.040*
H3A2	0.223 (3)	0.270 (3)	0.6914 (11)	0.040*
C1A	0.1547 (3)	0.0124 (3)	0.9087 (3)	0.0301 (8)
C2A	0.1455 (3)	−0.0700 (3)	0.9905 (3)	0.0390 (10)
H2A	0.1519	−0.0722	1.0490	0.047*
C3A	0.1267 (4)	−0.1485 (4)	0.9835 (3)	0.0476 (12)
H3A	0.1196	−0.2059	1.0385	0.057*
C4A	0.1180 (4)	−0.1458 (3)	0.8980 (4)	0.0461 (11)
H4A	0.1062	−0.2019	0.8954	0.055*
C5A	0.1261 (3)	−0.0634 (3)	0.8164 (3)	0.0383 (10)
H5A	0.1186	−0.0610	0.7584	0.046*
C6A	0.1455 (3)	0.0157 (3)	0.8228 (3)	0.0289 (8)
C7A	0.1852 (3)	0.1541 (3)	0.7961 (3)	0.0276 (8)
N1B	0.3312 (3)	0.4259 (2)	0.0564 (2)	0.0255 (7)
H1BA	0.342 (3)	0.388 (2)	0.022 (2)	0.031*
N2B	0.3232 (3)	0.4453 (2)	0.1903 (2)	0.0259 (7)
H2BA	0.309 (3)	0.433 (3)	0.2534 (9)	0.031*
N3B	0.2926 (3)	0.2980 (2)	0.2034 (2)	0.0290 (7)
H3B1	0.262 (3)	0.282 (3)	0.2670 (8)	0.035*
H3B2	0.287 (3)	0.258 (2)	0.179 (2)	0.035*
C1B	0.3467 (3)	0.5294 (3)	0.1157 (3)	0.0271 (8)
C2B	0.3658 (3)	0.6120 (3)	0.1150 (3)	0.0342 (9)
H2B	0.3626	0.6199	0.1733	0.041*
C3B	0.3900 (3)	0.6832 (3)	0.0250 (3)	0.0411 (10)
H3B	0.4040	0.7408	0.0216	0.049*
C4B	0.3939 (3)	0.6712 (3)	−0.0596 (3)	0.0414 (10)
H4B	0.4093	0.7217	−0.1196	0.050*
C5B	0.3761 (3)	0.5883 (3)	−0.0591 (3)	0.0333 (9)
H5B	0.3799	0.5803	−0.1175	0.040*
C6B	0.3525 (3)	0.5170 (3)	0.0300 (3)	0.0278 (8)
C7B	0.3140 (3)	0.3840 (3)	0.1536 (2)	0.0242 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ho1A	0.02226 (9)	0.02018 (9)	0.01649 (8)	−0.00801 (7)	−0.00717 (6)	−0.00445 (6)
Ho1B	0.02361 (9)	0.02101 (9)	0.01560 (8)	−0.00842 (7)	−0.00490 (6)	−0.00392 (6)
O11A	0.0253 (13)	0.0365 (15)	0.0242 (13)	−0.0127 (11)	−0.0032 (11)	−0.0136 (11)
O21A	0.0274 (14)	0.0380 (15)	0.0236 (13)	−0.0087 (11)	−0.0081 (11)	−0.0130 (11)
C11A	0.0242 (19)	0.0226 (18)	0.0260 (19)	−0.0053 (15)	−0.0089 (15)	−0.0063 (15)
C21A	0.024 (2)	0.042 (2)	0.034 (2)	−0.0108 (17)	−0.0080 (17)	−0.0131 (18)
C31A	0.026 (2)	0.033 (2)	0.027 (2)	−0.0073 (16)	−0.0041 (16)	−0.0075 (16)
C41A	0.040 (3)	0.042 (3)	0.031 (2)	−0.013 (2)	0.0013 (19)	−0.0060 (19)
O12A	0.0409 (15)	0.0239 (13)	0.0275 (14)	−0.0099 (11)	−0.0191 (12)	−0.0039 (11)
O22A	0.0396 (15)	0.0249 (13)	0.0244 (14)	−0.0077 (11)	−0.0148 (12)	−0.0058 (11)
C12A	0.0271 (19)	0.0232 (18)	0.0205 (18)	−0.0087 (15)	−0.0039 (15)	−0.0040 (15)
C22A	0.041 (2)	0.027 (2)	0.024 (2)	−0.0065 (17)	−0.0088 (17)	−0.0065 (16)
C32A	0.059 (3)	0.027 (2)	0.049 (3)	−0.012 (2)	−0.031 (2)	0.0029 (19)
C42A	0.070 (4)	0.036 (3)	0.063 (3)	−0.013 (2)	−0.038 (3)	0.008 (2)
O13A	0.0270 (13)	0.0259 (13)	0.0190 (12)	−0.0135 (11)	−0.0067 (10)	−0.0036 (10)
O23A	0.0256 (14)	0.0278 (14)	0.0240 (13)	−0.0102 (11)	−0.0060 (11)	0.0005 (11)
C13A	0.0297 (19)	0.0232 (18)	0.0141 (16)	−0.0113 (15)	−0.0061 (14)	−0.0039 (14)
C23A	0.030 (2)	0.027 (2)	0.031 (2)	−0.0112 (16)	−0.0082 (17)	−0.0028 (16)
C33A	0.030 (2)	0.034 (2)	0.028 (2)	−0.0146 (17)	−0.0095 (17)	0.0008 (17)
C43A	0.039 (3)	0.060 (3)	0.053 (3)	−0.032 (2)	−0.017 (2)	0.016 (2)
O14A	0.0285 (13)	0.0242 (13)	0.0232 (13)	−0.0061 (11)	−0.0130 (11)	−0.0069 (10)
O24A	0.0294 (14)	0.0253 (13)	0.0217 (13)	−0.0117 (11)	−0.0108 (11)	−0.0036 (10)
C14A	0.0206 (17)	0.0269 (18)	0.0199 (17)	−0.0122 (15)	−0.0053 (14)	−0.0052 (14)
C24A	0.031 (2)	0.031 (2)	0.028 (2)	−0.0112 (16)	−0.0098 (16)	−0.0115 (16)
C34A	0.033 (2)	0.044 (2)	0.025 (2)	−0.0056 (18)	−0.0112 (17)	−0.0146 (18)
C44A	0.059 (3)	0.072 (3)	0.028 (2)	−0.001 (3)	−0.022 (2)	−0.022 (2)
O11B	0.0319 (15)	0.0434 (16)	0.0238 (14)	−0.0170 (13)	−0.0098 (12)	0.0013 (12)
O21B	0.0257 (14)	0.0418 (16)	0.0233 (14)	−0.0106 (12)	−0.0065 (11)	−0.0083 (12)
C11B	0.028 (2)	0.0201 (18)	0.030 (2)	−0.0084 (15)	−0.0084 (16)	−0.0049 (15)
C21B	0.029 (2)	0.040 (2)	0.035 (2)	−0.0085 (18)	−0.0158 (18)	0.0003 (18)
C31B	0.029 (2)	0.073 (3)	0.042 (3)	−0.012 (2)	−0.011 (2)	−0.003 (2)
C41B	0.030 (3)	0.161 (7)	0.055 (4)	−0.025 (4)	−0.011 (3)	0.004 (4)
O12B	0.0444 (16)	0.0252 (13)	0.0189 (13)	−0.0121 (12)	−0.0064 (12)	−0.0037 (11)
O22B	0.0354 (15)	0.0261 (13)	0.0214 (13)	−0.0064 (11)	−0.0106 (11)	−0.0063 (11)
C12B	0.0207 (18)	0.0243 (18)	0.0274 (19)	−0.0071 (15)	−0.0082 (15)	−0.0058 (15)
C22B	0.047 (2)	0.027 (2)	0.028 (2)	−0.0141 (18)	−0.0147 (18)	−0.0049 (16)
C32B	0.041 (2)	0.031 (2)	0.038 (2)	−0.0103 (18)	−0.0167 (19)	−0.0109 (18)
C42B	0.070 (3)	0.033 (2)	0.053 (3)	−0.007 (2)	−0.025 (3)	−0.019 (2)
O13B	0.0273 (13)	0.0255 (13)	0.0208 (13)	−0.0130 (11)	−0.0048 (10)	−0.0053 (10)
O23B	0.0305 (14)	0.0257 (13)	0.0321 (14)	−0.0096 (11)	−0.0111 (12)	−0.0088 (11)
C13B	0.0284 (19)	0.0249 (18)	0.0155 (17)	−0.0111 (15)	−0.0068 (14)	−0.0017 (14)
C23B	0.030 (2)	0.027 (2)	0.046 (2)	−0.0098 (17)	−0.0133 (18)	−0.0086 (18)
C33B	0.037 (2)	0.031 (2)	0.041 (2)	−0.0146 (18)	−0.0157 (19)	−0.0034 (18)
C43B	0.039 (3)	0.051 (3)	0.077 (4)	−0.026 (2)	−0.021 (3)	−0.007 (3)
O14B	0.0284 (14)	0.0259 (13)	0.0190 (12)	−0.0071 (11)	−0.0063 (10)	−0.0062 (10)
O24B	0.0333 (14)	0.0253 (13)	0.0163 (12)	−0.0102 (11)	−0.0057 (11)	−0.0040 (10)
C14B	0.0234 (18)	0.0290 (19)	0.0177 (17)	−0.0128 (15)	−0.0054 (14)	−0.0036 (15)
C24B	0.033 (2)	0.036 (2)	0.0166 (18)	−0.0122 (17)	−0.0074 (15)	−0.0013 (16)
C34B	0.034 (2)	0.050 (3)	0.028 (2)	−0.0068 (19)	−0.0098 (18)	−0.0154 (19)
C44B	0.059 (3)	0.113 (5)	0.032 (3)	−0.017 (3)	−0.016 (2)	−0.036 (3)
N1A	0.0334 (18)	0.0367 (18)	0.0225 (16)	−0.0125 (14)	−0.0133 (14)	−0.0072 (14)
N2A	0.0303 (17)	0.045 (2)	0.0227 (16)	−0.0134 (15)	−0.0126 (14)	−0.0101 (14)
N3A	0.041 (2)	0.0364 (19)	0.0314 (18)	−0.0152 (16)	−0.0206 (16)	−0.0054 (15)
C1A	0.0245 (19)	0.044 (2)	0.026 (2)	−0.0122 (17)	−0.0113 (16)	−0.0078 (17)
C2A	0.034 (2)	0.057 (3)	0.025 (2)	−0.019 (2)	−0.0141 (17)	0.0008 (19)
C3A	0.046 (3)	0.051 (3)	0.045 (3)	−0.024 (2)	−0.025 (2)	0.009 (2)
C4A	0.046 (3)	0.041 (3)	0.061 (3)	−0.019 (2)	−0.029 (2)	−0.003 (2)
C5A	0.043 (2)	0.038 (2)	0.043 (2)	−0.0122 (19)	−0.026 (2)	−0.0073 (19)
C6A	0.0266 (19)	0.038 (2)	0.0258 (19)	−0.0101 (16)	−0.0135 (16)	−0.0059 (16)
C7A	0.0225 (19)	0.036 (2)	0.0275 (19)	−0.0035 (16)	−0.0126 (16)	−0.0123 (17)
N1B	0.0329 (17)	0.0293 (17)	0.0179 (15)	−0.0160 (14)	−0.0032 (13)	−0.0083 (13)
N2B	0.0321 (17)	0.0292 (16)	0.0208 (15)	−0.0152 (14)	−0.0055 (13)	−0.0080 (13)
N3B	0.044 (2)	0.0285 (17)	0.0181 (15)	−0.0201 (15)	−0.0034 (14)	−0.0071 (13)
C1B	0.0246 (19)	0.0263 (19)	0.029 (2)	−0.0091 (15)	−0.0049 (15)	−0.0090 (16)
C2B	0.035 (2)	0.032 (2)	0.043 (2)	−0.0145 (18)	−0.0085 (19)	−0.0156 (18)
C3B	0.038 (2)	0.028 (2)	0.056 (3)	−0.0152 (18)	−0.008 (2)	−0.012 (2)
C4B	0.037 (2)	0.030 (2)	0.043 (3)	−0.0152 (19)	−0.0041 (19)	−0.0007 (19)
C5B	0.033 (2)	0.033 (2)	0.027 (2)	−0.0120 (17)	−0.0064 (17)	−0.0049 (17)
C6B	0.0256 (19)	0.0263 (19)	0.029 (2)	−0.0107 (15)	−0.0032 (16)	−0.0089 (16)
C7B	0.0266 (19)	0.0275 (19)	0.0184 (17)	−0.0111 (15)	−0.0032 (14)	−0.0076 (15)

Geometric parameters (Å, º)

Ho1A—O14A	2.290 (2)	O12B—C12B	1.263 (4)
Ho1A—O13A^i	2.316 (2)	O22B—C12B	1.264 (4)
Ho1A—O24A^i	2.321 (2)	C12B—C22B	1.482 (5)
Ho1A—O23A	2.394 (2)	C22B—C32B	1.321 (5)
Ho1A—O11A	2.438 (2)	C22B—H22B	0.9500
Ho1A—O22A	2.446 (2)	C32B—C42B	1.493 (5)
Ho1A—O12A	2.467 (2)	C32B—H32B	0.9500
Ho1A—O21A	2.483 (2)	C42B—H42D	0.9800
Ho1A—O13A	2.523 (2)	C42B—H42E	0.9800
Ho1B—O13B^ii	2.305 (2)	C42B—H42F	0.9800
Ho1B—O14B	2.308 (2)	O13B—C13B	1.277 (4)
Ho1B—O24B^ii	2.309 (2)	O13B—Ho1B^ii	2.305 (2)
Ho1B—O23B	2.417 (2)	O23B—C13B	1.253 (4)
Ho1B—O12B	2.422 (2)	C13B—C23B	1.473 (5)
Ho1B—O21B	2.458 (2)	C23B—C33B	1.321 (5)
Ho1B—O22B	2.476 (2)	C23B—H23B	0.9500
Ho1B—O11B	2.492 (3)	C33B—C43B	1.498 (6)
Ho1B—O13B	2.531 (2)	C33B—H33B	0.9500
O11A—C11A	1.259 (4)	C43B—H43D	0.9800
O21A—C11A	1.260 (4)	C43B—H43E	0.9800
C11A—C21A	1.488 (5)	C43B—H43F	0.9800
C21A—C31A	1.323 (5)	O14B—C14B	1.258 (4)
C21A—H21A	0.9500	O24B—C14B	1.268 (4)
C31A—C41A	1.495 (5)	O24B—Ho1B^ii	2.309 (2)
C31A—H31A	0.9500	C14B—C24B	1.491 (5)
C41A—H41A	0.9800	C24B—C34B	1.315 (5)
C41A—H41B	0.9800	C24B—H24B	0.9500
C41A—H41C	0.9800	C34B—C44B	1.502 (6)
O12A—C12A	1.262 (4)	C34B—H34B	0.9500
O22A—C12A	1.267 (4)	C44B—H44D	0.9800
C12A—C22A	1.479 (5)	C44B—H44E	0.9800
C22A—C32A	1.303 (5)	C44B—H44F	0.9800
C22A—H22A	0.9500	N1A—C7A	1.351 (5)
C32A—C42A	1.504 (5)	N1A—C6A	1.391 (5)
C32A—H32A	0.9500	N1A—H1AA	0.87 (3)
C42A—H42A	0.9800	N2A—C7A	1.352 (5)
C42A—H42B	0.9800	N2A—C1A	1.385 (5)
C42A—H42C	0.9800	N2A—H2AA	0.89 (4)
O13A—C13A	1.281 (4)	N3A—C7A	1.299 (5)
O13A—Ho1A^i	2.316 (2)	N3A—H3A1	0.87 (5)
O23A—C13A	1.243 (4)	N3A—H3A2	0.87 (2)
C13A—C23A	1.475 (5)	C1A—C2A	1.385 (5)
C23A—C33A	1.311 (5)	C1A—C6A	1.394 (5)
C23A—H23A	0.9500	C2A—C3A	1.377 (6)
C33A—C43A	1.480 (5)	C2A—H2A	0.9500
C33A—H33A	0.9500	C3A—C4A	1.387 (6)
C43A—H43A	0.9800	C3A—H3A	0.9500
C43A—H43B	0.9800	C4A—C5A	1.384 (6)
C43A—H43C	0.9800	C4A—H4A	0.9500
O14A—C14A	1.261 (4)	C5A—C6A	1.386 (5)
O24A—C14A	1.266 (4)	C5A—H5A	0.9500
O24A—Ho1A^i	2.321 (2)	N1B—C7B	1.351 (4)
C14A—C24A	1.489 (5)	N1B—C6B	1.395 (4)
C24A—C34A	1.309 (5)	N1B—H1BA	0.87 (3)
C24A—H24A	0.9500	N2B—C7B	1.344 (4)
C34A—C44A	1.509 (5)	N2B—C1B	1.387 (5)
C34A—H34A	0.9500	N2B—H2BA	0.87 (2)
C44A—H44A	0.9800	N3B—C7B	1.306 (4)
C44A—H44B	0.9800	N3B—H3B1	0.87 (2)
C44A—H44C	0.9800	N3B—H3B2	0.88 (3)
O11B—C11B	1.258 (4)	C1B—C2B	1.382 (5)
O21B—C11B	1.259 (4)	C1B—C6B	1.395 (5)
C11B—C21B	1.482 (5)	C2B—C3B	1.394 (6)
C21B—C31B	1.311 (6)	C2B—H2B	0.9500
C21B—H21B	0.9500	C3B—C4B	1.388 (6)
C31B—C41B	1.489 (6)	C3B—H3B	0.9500
C31B—H31B	0.9500	C4B—C5B	1.376 (5)
C41B—H41D	0.9800	C4B—H4B	0.9500
C41B—H41E	0.9800	C5B—C6B	1.385 (5)
C41B—H41F	0.9800	C5B—H5B	0.9500
Ho1A···Ho1A^i	3.8418 (3)	Ho1B···Ho1B^ii	3.8246 (3)
O14A—Ho1A—O13A^i	76.52 (8)	C13A—O23A—Ho1A	96.3 (2)
O14A—Ho1A—O24A^i	138.53 (8)	O23A—C13A—O13A	120.4 (3)
O13A^i—Ho1A—O24A^i	76.76 (8)	O23A—C13A—C23A	120.9 (3)
O14A—Ho1A—O23A	92.71 (9)	O13A—C13A—C23A	118.7 (3)
O13A^i—Ho1A—O23A	127.05 (8)	O23A—C13A—Ho1A	57.67 (18)
O24A^i—Ho1A—O23A	78.95 (8)	O13A—C13A—Ho1A	63.63 (18)
O14A—Ho1A—O11A	129.60 (8)	C23A—C13A—Ho1A	168.3 (2)
O13A^i—Ho1A—O11A	77.56 (8)	C33A—C23A—C13A	123.5 (4)
O24A^i—Ho1A—O11A	73.40 (8)	C33A—C23A—H23A	118.2
O23A—Ho1A—O11A	136.98 (8)	C13A—C23A—H23A	118.2
O14A—Ho1A—O22A	129.48 (8)	C23A—C33A—C43A	126.4 (4)
O13A^i—Ho1A—O22A	149.03 (8)	C23A—C33A—H33A	116.8
O24A^i—Ho1A—O22A	87.51 (8)	C43A—C33A—H33A	116.8
O23A—Ho1A—O22A	74.12 (8)	C33A—C43A—H43A	109.5
O11A—Ho1A—O22A	72.39 (8)	C33A—C43A—H43B	109.5
O14A—Ho1A—O12A	76.56 (8)	H43A—C43A—H43B	109.5
O13A^i—Ho1A—O12A	145.33 (8)	C33A—C43A—H43C	109.5
O24A^i—Ho1A—O12A	137.46 (8)	H43A—C43A—H43C	109.5
O23A—Ho1A—O12A	75.66 (8)	H43B—C43A—H43C	109.5
O11A—Ho1A—O12A	103.85 (8)	C14A—O14A—Ho1A	137.1 (2)
O22A—Ho1A—O12A	52.99 (8)	C14A—O24A—Ho1A^i	132.6 (2)
O14A—Ho1A—O21A	80.98 (8)	O14A—C14A—O24A	125.9 (3)
O13A^i—Ho1A—O21A	81.40 (8)	O14A—C14A—C24A	117.8 (3)
O24A^i—Ho1A—O21A	125.11 (8)	O24A—C14A—C24A	116.3 (3)
O23A—Ho1A—O21A	148.78 (8)	C34A—C24A—C14A	121.6 (3)
O11A—Ho1A—O21A	52.84 (8)	C34A—C24A—H24A	119.2
O22A—Ho1A—O21A	86.38 (9)	C14A—C24A—H24A	119.2
O12A—Ho1A—O21A	73.14 (8)	C24A—C34A—C44A	125.0 (4)
O14A—Ho1A—O13A	71.27 (8)	C24A—C34A—H34A	117.5
O13A^i—Ho1A—O13A	74.96 (9)	C44A—C34A—H34A	117.5
O24A^i—Ho1A—O13A	71.53 (8)	C34A—C44A—H44A	109.5
O23A—Ho1A—O13A	52.81 (8)	C34A—C44A—H44B	109.5
O11A—Ho1A—O13A	139.34 (8)	H44A—C44A—H44B	109.5
O22A—Ho1A—O13A	125.24 (8)	C34A—C44A—H44C	109.5
O12A—Ho1A—O13A	115.82 (8)	H44A—C44A—H44C	109.5
O21A—Ho1A—O13A	146.88 (8)	H44B—C44A—H44C	109.5
O14A—Ho1A—C13A	83.92 (9)	C11B—O11B—Ho1B	92.9 (2)
O13A^i—Ho1A—C13A	101.10 (9)	C11B—O21B—Ho1B	94.4 (2)
O24A^i—Ho1A—C13A	70.86 (9)	O11B—C11B—O21B	120.3 (3)
O23A—Ho1A—C13A	26.03 (8)	O11B—C11B—C21B	119.4 (3)
O11A—Ho1A—C13A	143.48 (9)	O21B—C11B—C21B	120.4 (3)
O22A—Ho1A—C13A	98.57 (9)	O11B—C11B—Ho1B	60.94 (19)
O12A—Ho1A—C13A	97.36 (9)	O21B—C11B—Ho1B	59.39 (18)
O21A—Ho1A—C13A	163.68 (9)	C21B—C11B—Ho1B	178.4 (3)
O13A—Ho1A—C13A	27.05 (8)	C31B—C21B—C11B	123.2 (4)
O14A—Ho1A—C11A	104.89 (9)	C31B—C21B—H21B	118.4
O13A^i—Ho1A—C11A	76.37 (9)	C11B—C21B—H21B	118.4
O24A^i—Ho1A—C11A	98.89 (9)	C21B—C31B—C41B	126.8 (5)
O23A—Ho1A—C11A	154.10 (9)	C21B—C31B—H31B	116.6
O11A—Ho1A—C11A	26.44 (9)	C41B—C31B—H31B	116.6
O22A—Ho1A—C11A	80.01 (9)	C31B—C41B—H41D	109.5
O12A—Ho1A—C11A	89.90 (9)	C31B—C41B—H41E	109.5
O21A—Ho1A—C11A	26.52 (9)	H41D—C41B—H41E	109.5
O13A—Ho1A—C11A	151.17 (9)	C31B—C41B—H41F	109.5
C13A—Ho1A—C11A	169.74 (10)	H41D—C41B—H41F	109.5
O14A—Ho1A—C12A	103.02 (9)	H41E—C41B—H41F	109.5
O13A^i—Ho1A—C12A	159.05 (9)	C12B—O12B—Ho1B	94.7 (2)
O24A^i—Ho1A—C12A	113.07 (9)	C12B—O22B—Ho1B	92.1 (2)
O23A—Ho1A—C12A	73.82 (9)	O12B—C12B—O22B	120.1 (3)
O11A—Ho1A—C12A	87.41 (9)	O12B—C12B—C22B	120.0 (3)
O22A—Ho1A—C12A	26.56 (9)	O22B—C12B—C22B	119.8 (3)
O12A—Ho1A—C12A	26.46 (9)	O12B—C12B—Ho1B	58.83 (18)
O21A—Ho1A—C12A	77.88 (9)	O22B—C12B—Ho1B	61.28 (18)
O13A—Ho1A—C12A	125.18 (9)	C22B—C12B—Ho1B	178.8 (3)
C13A—Ho1A—C12A	99.66 (10)	C32B—C22B—C12B	123.7 (4)
C11A—Ho1A—C12A	83.66 (10)	C32B—C22B—H22B	118.2
O13B^ii—Ho1B—O14B	77.36 (8)	C12B—C22B—H22B	118.2
O13B^ii—Ho1B—O24B^ii	77.01 (8)	C22B—C32B—C42B	125.9 (4)
O14B—Ho1B—O24B^ii	138.71 (8)	C22B—C32B—H32B	117.0
O13B^ii—Ho1B—O23B	127.98 (8)	C42B—C32B—H32B	117.0
O14B—Ho1B—O23B	84.60 (9)	C32B—C42B—H42D	109.5
O24B^ii—Ho1B—O23B	86.29 (9)	C32B—C42B—H42E	109.5
O13B^ii—Ho1B—O12B	146.80 (8)	H42D—C42B—H42E	109.5
O14B—Ho1B—O12B	83.65 (8)	C32B—C42B—H42F	109.5
O24B^ii—Ho1B—O12B	132.49 (8)	H42D—C42B—H42F	109.5
O23B—Ho1B—O12B	76.03 (9)	H42E—C42B—H42F	109.5
O13B^ii—Ho1B—O21B	77.98 (8)	C13B—O13B—Ho1B^ii	164.6 (2)
O14B—Ho1B—O21B	77.50 (8)	C13B—O13B—Ho1B	90.7 (2)
O24B^ii—Ho1B—O21B	127.05 (9)	Ho1B^ii—O13B—Ho1B	104.45 (9)
O23B—Ho1B—O21B	144.22 (8)	C13B—O23B—Ho1B	96.6 (2)
O12B—Ho1B—O21B	71.43 (9)	O23B—C13B—O13B	119.7 (3)
O13B^ii—Ho1B—O22B	145.05 (8)	O23B—C13B—C23B	121.3 (3)
O14B—Ho1B—O22B	135.42 (8)	O13B—C13B—C23B	118.9 (3)
O24B^ii—Ho1B—O22B	80.04 (8)	O23B—C13B—Ho1B	57.47 (18)
O23B—Ho1B—O22B	75.75 (8)	O13B—C13B—Ho1B	62.67 (18)
O12B—Ho1B—O22B	53.09 (8)	C23B—C13B—Ho1B	171.6 (3)
O21B—Ho1B—O22B	95.74 (9)	C33B—C23B—C13B	124.3 (4)
O13B^ii—Ho1B—O11B	79.05 (9)	C33B—C23B—H23B	117.8
O14B—Ho1B—O11B	127.85 (8)	C13B—C23B—H23B	117.8
O24B^ii—Ho1B—O11B	77.45 (9)	C23B—C33B—C43B	125.8 (4)
O23B—Ho1B—O11B	144.43 (8)	C23B—C33B—H33B	117.1
O12B—Ho1B—O11B	91.92 (9)	C43B—C33B—H33B	117.1
O21B—Ho1B—O11B	52.32 (8)	C33B—C43B—H43D	109.5
O22B—Ho1B—O11B	70.43 (9)	C33B—C43B—H43E	109.5
O13B^ii—Ho1B—O13B	75.55 (9)	H43D—C43B—H43E	109.5
O14B—Ho1B—O13B	71.40 (8)	C33B—C43B—H43F	109.5
O24B^ii—Ho1B—O13B	71.19 (8)	H43D—C43B—H43F	109.5
O23B—Ho1B—O13B	52.44 (8)	H43E—C43B—H43F	109.5
O12B—Ho1B—O13B	123.53 (8)	C14B—O14B—Ho1B	136.3 (2)
O21B—Ho1B—O13B	142.68 (8)	C14B—O24B—Ho1B^ii	135.5 (2)
O22B—Ho1B—O13B	120.88 (8)	O14B—C14B—O24B	125.9 (3)
O11B—Ho1B—O13B	143.17 (8)	O14B—C14B—C24B	119.1 (3)
O13B^ii—Ho1B—C12B	157.50 (9)	O24B—C14B—C24B	115.1 (3)
O14B—Ho1B—C12B	109.67 (9)	C34B—C24B—C14B	123.3 (4)
O24B^ii—Ho1B—C12B	106.40 (9)	C34B—C24B—H24B	118.4
O23B—Ho1B—C12B	74.48 (9)	C14B—C24B—H24B	118.4
O12B—Ho1B—C12B	26.50 (9)	C24B—C34B—C44B	123.8 (4)
O21B—Ho1B—C12B	82.71 (9)	C24B—C34B—H34B	118.1
O22B—Ho1B—C12B	26.60 (9)	C44B—C34B—H34B	118.1
O11B—Ho1B—C12B	80.06 (9)	C34B—C44B—H44D	109.5
O13B—Ho1B—C12B	126.85 (9)	C34B—C44B—H44E	109.5
O13B^ii—Ho1B—C11B	77.90 (9)	H44D—C44B—H44E	109.5
O14B—Ho1B—C11B	102.96 (10)	C34B—C44B—H44F	109.5
O24B^ii—Ho1B—C11B	102.62 (10)	H44D—C44B—H44F	109.5
O23B—Ho1B—C11B	154.10 (9)	H44E—C44B—H44F	109.5
O12B—Ho1B—C11B	80.20 (10)	C7A—N1A—C6A	108.8 (3)
O21B—Ho1B—C11B	26.16 (9)	C7A—N1A—H1AA	130 (3)
O22B—Ho1B—C11B	81.86 (9)	C6A—N1A—H1AA	121 (3)
O11B—Ho1B—C11B	26.18 (9)	C7A—N2A—C1A	109.1 (3)
O13B—Ho1B—C11B	153.46 (9)	C7A—N2A—H2AA	121 (3)
C12B—Ho1B—C11B	79.67 (10)	C1A—N2A—H2AA	129 (3)
O13B^ii—Ho1B—C13B	102.15 (9)	C7A—N3A—H3A1	121 (2)
O14B—Ho1B—C13B	78.54 (9)	C7A—N3A—H3A2	126 (2)
O24B^ii—Ho1B—C13B	75.92 (9)	H3A1—N3A—H3A2	110 (2)
O23B—Ho1B—C13B	25.92 (9)	N2A—C1A—C2A	131.8 (4)
O12B—Ho1B—C13B	100.39 (10)	N2A—C1A—C6A	106.7 (3)
O21B—Ho1B—C13B	155.38 (9)	C2A—C1A—C6A	121.5 (4)
O22B—Ho1B—C13B	97.35 (9)	C3A—C2A—C1A	117.2 (4)
O11B—Ho1B—C13B	152.28 (9)	C3A—C2A—H2A	121.4
O13B—Ho1B—C13B	26.63 (8)	C1A—C2A—H2A	121.4
C12B—Ho1B—C13B	100.22 (10)	C2A—C3A—C4A	121.5 (4)
C11B—Ho1B—C13B	178.45 (10)	C2A—C3A—H3A	119.2
C11A—O11A—Ho1A	94.0 (2)	C4A—C3A—H3A	119.2
C11A—O21A—Ho1A	91.9 (2)	C5A—C4A—C3A	121.5 (4)
O11A—C11A—O21A	120.7 (3)	C5A—C4A—H4A	119.2
O11A—C11A—C21A	119.3 (3)	C3A—C4A—H4A	119.2
O21A—C11A—C21A	119.8 (3)	C4A—C5A—C6A	117.2 (4)
O11A—C11A—Ho1A	59.55 (18)	C4A—C5A—H5A	121.4
O21A—C11A—Ho1A	61.60 (18)	C6A—C5A—H5A	121.4
C21A—C11A—Ho1A	169.2 (3)	C5A—C6A—N1A	132.2 (3)
C31A—C21A—C11A	123.2 (4)	C5A—C6A—C1A	121.0 (4)
C31A—C21A—H21A	118.4	N1A—C6A—C1A	106.8 (3)
C11A—C21A—H21A	118.4	N3A—C7A—N1A	126.4 (4)
C21A—C31A—C41A	126.3 (4)	N3A—C7A—N2A	125.1 (3)
C21A—C31A—H31A	116.9	N1A—C7A—N2A	108.4 (3)
C41A—C31A—H31A	116.9	C7B—N1B—C6B	108.8 (3)
C31A—C41A—H41A	109.5	C7B—N1B—H1BA	117 (3)
C31A—C41A—H41B	109.5	C6B—N1B—H1BA	132 (3)
H41A—C41A—H41B	109.5	C7B—N2B—C1B	109.5 (3)
C31A—C41A—H41C	109.5	C7B—N2B—H2BA	121 (3)
H41A—C41A—H41C	109.5	C1B—N2B—H2BA	129 (2)
H41B—C41A—H41C	109.5	C7B—N3B—H3B1	124 (2)
C12A—O12A—Ho1A	93.0 (2)	C7B—N3B—H3B2	125 (2)
C12A—O22A—Ho1A	93.8 (2)	H3B1—N3B—H3B2	108 (2)
O12A—C12A—O22A	120.1 (3)	C2B—C1B—N2B	131.9 (4)
O12A—C12A—C22A	121.1 (3)	C2B—C1B—C6B	121.6 (4)
O22A—C12A—C22A	118.8 (3)	N2B—C1B—C6B	106.5 (3)
O12A—C12A—Ho1A	60.55 (18)	C1B—C2B—C3B	117.0 (4)
O22A—C12A—Ho1A	59.61 (17)	C1B—C2B—H2B	121.5
C22A—C12A—Ho1A	176.3 (3)	C3B—C2B—H2B	121.5
C32A—C22A—C12A	124.9 (4)	C4B—C3B—C2B	121.0 (4)
C32A—C22A—H22A	117.5	C4B—C3B—H3B	119.5
C12A—C22A—H22A	117.5	C2B—C3B—H3B	119.5
C22A—C32A—C42A	126.4 (4)	C5B—C4B—C3B	121.9 (4)
C22A—C32A—H32A	116.8	C5B—C4B—H4B	119.0
C42A—C32A—H32A	116.8	C3B—C4B—H4B	119.0
C32A—C42A—H42A	109.5	C4B—C5B—C6B	117.4 (4)
C32A—C42A—H42B	109.5	C4B—C5B—H5B	121.3
H42A—C42A—H42B	109.5	C6B—C5B—H5B	121.3
C32A—C42A—H42C	109.5	C5B—C6B—C1B	121.0 (3)
H42A—C42A—H42C	109.5	C5B—C6B—N1B	132.3 (3)
H42B—C42A—H42C	109.5	C1B—C6B—N1B	106.6 (3)
C13A—O13A—Ho1A^i	159.1 (2)	N3B—C7B—N2B	125.8 (3)
C13A—O13A—Ho1A	89.3 (2)	N3B—C7B—N1B	125.6 (3)
Ho1A^i—O13A—Ho1A	105.04 (9)	N2B—C7B—N1B	108.6 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···O22B	0.87 (3)	1.93 (3)	2.804 (4)	174 (4)
N2A—H2AA···O21A	0.89 (4)	1.97 (4)	2.849 (4)	171 (4)
N3A—H3A2···O11B	0.87 (2)	2.02 (2)	2.860 (4)	162 (4)
N3A—H3A1···O12A	0.87 (5)	1.95 (4)	2.820 (4)	172 (3)
N1B—H1BA···O22A^iii	0.87 (3)	1.87 (3)	2.722 (4)	170 (4)
N2B—H2BA···O21B	0.87 (2)	1.90 (2)	2.733 (4)	159 (3)
N3B—H3B1···O12B	0.87 (2)	2.03 (2)	2.889 (4)	168 (3)
N3B—H3B2···O11A^iii	0.88 (3)	1.94 (4)	2.814 (4)	174 (4)

Symmetry code: (iii) x, y, z−1.