Bis­(nateglinide) hydro­nium chloride, and its unique self-assembly into extended polymeric arrays via O—H...O, N—H...Cl and O—H...Cl hydrogen bonds

The title compound, bis­[(−)-N-(trans-4-isopropyl­cyclo­hexane­carbon­yl)-D-phenyl­alanine] hydro­nium chloride, 2C₁₉H₂₇NO₃·H₃O⁺·Cl⁻, at 110 K contains four conformationally dissimilar moieties in the asymmetric unit, which are seemingly necessary in order to optimize the supramolecular association. The organic mol­ecule forms O—H...O hydrogen-bonded carboxylic acid dimers, which are paired into six-component clusters via N—H...Cl hydrogen bonds through the two bridging chloride anions. These combined hexa­meric aggregates are further inter­linked into extended two-dimensional network arrays via the hydro­nium ions by O—H...O and O—H...Cl hydrogen bonds. This study represents the first crystallographic report of nateglinide.

S1. Comment

Nateglinide is an oral drug used to lower blood glucose levels in type 2 diabetes. It belongs to a class of drugs called meglitinides and gained FDA approval in December 2000. Nateglinide stimulates cells in the pancreas to produce insulin in a manner similar to the sulfonylurea insulin, although these two classes of insulin drugs are structurally unrelated. The first crystallographic determination of this pharmaceutically important material is described here; it could be crystallized only in the presence of dilute HCl. The title compound, (I), is a cocrystal of nateglinide and hydrated hydrochloric acid with a 2:1 stochiometric ratio. Incorporation of the latter into the crystal structure induces the formation of continuous hydrogen-bonding arrays, yielding a stable structure. Molecules of (I) are characterized by several degrees of conformational freedom, and the asymmetric unit consists of four organic species (labeled as A, B, C and D) of different conformations (Table 1) and two hydrated HCl moieties (Fig. 1). It should be noted that the cocrystallization with HCl did not result (as often observed) in protonation of the basic NH site in the drug. Rather, in this structure, the hydrochloric acid, in the form of H₃O⁺·Cl⁻, was found to act as a multiple hydrogen-bond donor and acceptor to direct the formation of supramolecular networks by bridging between the organic components. Nateglinide contains two proton donors (the –COOH and –NH sites) and two proton acceptors (the COOH and C═O sites), all being effectively utilized. The hydrogen-bonding pattern can be best described in the following modular manner. Firstly, the organic molecules are paired by self-complementary O—H···O═C cyclic interactions through their carboxylic acid functions (Table 2). Then, two such self-assembled pairs are joined into a larger hydrogen-bonded assembly by two Cl⁻ ions, each attracting an H atom from the NH sites of two neighboring units (Fig. 2 and Table 2). These Cl-bridged oligomeric entities are further cross-linked by additional hydrogen bonding through the hydronium ions. The latter donate their H atoms to amide atoms O3 of adjacent species, as well as to chloride ions. This cooperative multiple hydrogen bonding leads to the formation of supramolecular networks, which are perpendicular to the a axis of the crystal and center around x = 0 and x = 1/2 (Fig. 3 and Table 2). All the H-atom donating and accepting functions are embedded within these layers, while the hydrophobic isopropylcyclohexane and phenyl residues line the upper and lower surfaces of the layers.

Stacking of the hydrogen-bonded networks along (100) is thus stabilized by common van der Waals interactions between the hydrophobic surfaces (Fig. 4). The conformational flexibility of the nateglinide molecular framework, while preserving the chair conformation of the cyclohexyl residue, is demonstrated in Table 1 by the different torsion angles associated with the benzyl, isopropylcyclohexyl and carboxyl groups in the four independent molecules of the asymmetric unit. The four-molecule content of the asymmetric unit is seemingly required to optimize the inter-particle dispersive and multiple hydrogen-bonding interactions in the crystal structure.

All the bond lengths and bond angles are in the normal range, and the observed results distinguish clearly between the C═O_carbonyl and C—O_hydroxy bonds in the carboxylic acid groups. The short O—H···O hydrogen-bonding distances, within the range 2.454–2.530 Å, involving O4 and O5 are consistent with the positively charged hydronium identity of these species (Jeffrey, 1997). Evidently, the bifurcated N—H···Cl⁻ interactions are much weaker than the H₃O⁺···Cl⁻ interactions (Table 2). The apparent optimization of the hydrogen-bonding scheme leads to a somewhat inefficient crystal packing of relatively low density, which contains two solvent-accessible voids of ca 80 ų that are centered along the interface between the hydrogen-bonded layers at (0.49, 0.22, 0.18) and (0.51, 0.72, 0.82). The terminal isopropyl groups that point into these voids reveal some disorder, reflected in the large-amplitude displacement ellipsoids of their respective atoms (particularly the C17C–C19C fragment). The total residual electron density in the void spaces was assessed to be ten electrons per unit cell (Spek, 2003), which is consistent with the rather minor conformational disorder in the structure. A survey of the Cambridge Structural Database (Allen, 2002) indicates that no structures of similar composition (cyclohexane carbonyl and phenylalanine residues joined through an amide bond) and connectivity have been reported as yet. Multicomponent supramolecular assemblies sustained simultaneously by (COOH)₂ cyclic dimeric and N—H···Cl···H—N hydrogen bonds have not been found either, although separate appearances of these two synthons are quite abundant in organic crystals (Allen, 2002; Chang et al., 1993; Chekmenev et al., 2004).

S2. Experimental

Compound (I) was crystallized by dissolving nateglinide (0.0291 g) in 1.0 M HCl (4 ml) at 353 K, followed by slow cooling and evaporation.

S3. Refinement

The H atoms bound to C were located in idealized positions (C—H = 0.95–1.00 Å); they were refined with fixed displacement parameters [U_iso(H) = 1.2U_eq(C) or 1.5 U_eq(C)] using a riding model. H atoms attached to O and N atoms were located reliably in difference Fourier maps and included in the refinement calculations with isotropic displacement parameters and distance restraints imposed on the O—H and N—H bonds. The minor disorder apparent in some of the isopropyl fragments could not be resolved.

Computing details

Data collection: Collect (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Compound (I), with the atom-labeling scheme. Displacement ellipsoids are shown at the 50% probability level; the four crystallographically independent molecules of nateglinide are denoted A–D.
	Fig. 2. The self-assembled multicomponent asymmetric unit with hydrogen bonding through the COOH dimers and the two chloride ion bridges. For clarity, only H atoms that are involved in hydrogen bonds (dashed lines) are shown. [In the online version of the journal, the hydrogen bonds involving O and Cl atoms are denoted by red and blue dashed lines, respectively. Online color code: Cl green, O red, N blue, C gray, H white.]
	Fig. 3. A face-on illustration of the continuous hydrogen-bonded networks normal to (100), showing further aggregation of the organic tetramers into two-dimensional arrays by cross-linking through the hydronium ions. For clarity, molecules are represented only by their central C—C(COOH)—NH—CO—C fragment; the hydronium and chloride ions are represented by small spheres. [In the online version of the journal, the hydrogen bonds involving O and Cl atoms are denoted by red and blue dashed lines, respectively. Online color code: Cl green, O red, N blue, C black.]
	Fig. 4. The crystal packing, viewed down (001), showing alternating hydrophilic zones (within the hydrogen-bonded layers) and hydrophobic zones (between the layers). The molecules are shown as a stick diagram, except for the hydronium and chloride ions, which are represented by small spheres.

hydronium bis[(-)-N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine] chloride

Crystal data

H3O^+·2C19H27NO3·Cl^−	F(000) = 1488
Mr = 689.31	Dx = 1.152 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8475 reflections
a = 14.0121 (2) Å	θ = 1.6–27.9°
b = 19.6631 (3) Å	µ = 0.14 mm^−1
c = 15.3773 (2) Å	T = 110 K
β = 110.2998 (8)°	Prism, colorless
V = 3973.62 (10) Å^3	0.35 × 0.30 × 0.20 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	11365 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
Graphite monochromator	θmax = 27.9°, θmin = 1.6°
Detector resolution: 56 microns pixels mm^-1	h = −18→18
1° ϕ and ω scans	k = −25→23
29123 measured reflections	l = −20→19
15992 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2) + (0.0461P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.115	(Δ/σ)max = 0.012
S = 1.03	Δρmax = 0.41 e Å^−3
15992 reflections	Δρmin = −0.24 e Å^−3
931 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
15 restraints	Extinction coefficient: 0.0041 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 6258 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.01 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1A	0.20872 (17)	0.44495 (13)	0.26843 (15)	0.0421 (6)
O2A	0.03948 (15)	0.43870 (11)	0.20075 (13)	0.0274 (5)
HO2A	0.039 (4)	0.443 (3)	0.2621 (18)	0.115 (19)*
O3A	0.05653 (16)	0.54137 (10)	0.04352 (14)	0.0286 (5)
N1A	0.04733 (19)	0.42829 (13)	0.03008 (16)	0.0243 (5)
HN1A	0.012 (2)	0.3881 (12)	0.005 (2)	0.039 (9)*
C1A	0.3361 (2)	0.36816 (19)	0.0582 (2)	0.0395 (8)
H1A	0.3674	0.3931	0.1137	0.047*
C2A	0.3864 (3)	0.3606 (2)	−0.0041 (3)	0.0492 (10)
H2A	0.4515	0.3806	0.0083	0.059*
C3A	0.3419 (3)	0.32414 (18)	−0.0844 (3)	0.0468 (10)
H3A	0.3764	0.3187	−0.1274	0.056*
C4A	0.2479 (3)	0.29565 (18)	−0.1023 (3)	0.0506 (10)
H4A	0.2171	0.2707	−0.1580	0.061*
C5A	0.1966 (3)	0.30299 (17)	−0.0390 (2)	0.0410 (9)
H5A	0.1318	0.2826	−0.0513	0.049*
C6A	0.2410 (2)	0.33995 (16)	0.0410 (2)	0.0300 (7)
C7A	0.1878 (2)	0.34934 (15)	0.1109 (2)	0.0281 (7)
H7E	0.2371	0.3411	0.1740	0.034*
H7F	0.1326	0.3153	0.0988	0.034*
C8A	0.1427 (2)	0.42098 (15)	0.1068 (2)	0.0269 (7)
H8A	0.1923	0.4542	0.0973	0.032*
C9A	0.1311 (2)	0.43678 (15)	0.1994 (2)	0.0284 (7)
C10A	0.0060 (2)	0.48933 (15)	0.00553 (19)	0.0239 (6)
C11A	−0.1012 (2)	0.49611 (15)	−0.06109 (19)	0.0249 (6)
H11A	−0.1068	0.5415	−0.0919	0.030*
C12A	−0.1356 (2)	0.44242 (15)	−0.13777 (19)	0.0278 (7)
H12E	−0.0908	0.4440	−0.1754	0.033*
H12F	−0.1296	0.3966	−0.1096	0.033*
C13A	−0.2456 (2)	0.45471 (16)	−0.2002 (2)	0.0294 (7)
H13E	−0.2670	0.4180	−0.2471	0.035*
H13F	−0.2497	0.4983	−0.2335	0.035*
C14A	−0.3185 (2)	0.45692 (15)	−0.1459 (2)	0.0297 (7)
H14A	−0.3121	0.4119	−0.1140	0.036*
C15A	−0.2833 (2)	0.51013 (17)	−0.0694 (2)	0.0316 (7)
H15E	−0.3290	0.5095	−0.0327	0.038*
H15F	−0.2875	0.5558	−0.0976	0.038*
C16A	−0.1738 (2)	0.49665 (17)	−0.0054 (2)	0.0304 (7)
H16E	−0.1704	0.4523	0.0260	0.036*
H16F	−0.1524	0.5324	0.0429	0.036*
C17A	−0.4309 (2)	0.46328 (17)	−0.2094 (2)	0.0333 (7)
H17A	−0.4448	0.4256	−0.2558	0.040*
C18A	−0.5035 (3)	0.45362 (19)	−0.1550 (2)	0.0425 (8)
H18E	−0.4994	0.4933	−0.1153	0.064*
H18F	−0.4841	0.4127	−0.1164	0.064*
H18G	−0.5734	0.4487	−0.1985	0.064*
C19A	−0.4570 (3)	0.53024 (19)	−0.2639 (3)	0.0475 (9)
H19E	−0.5289	0.5300	−0.3034	0.071*
H19F	−0.4146	0.5350	−0.3026	0.071*
H19G	−0.4440	0.5685	−0.2204	0.071*
O1B	−0.32721 (16)	0.51923 (11)	0.15757 (16)	0.0371 (5)
O2B	−0.15894 (15)	0.51443 (10)	0.23166 (14)	0.0261 (4)
HO2B	−0.162 (4)	0.4669 (11)	0.221 (3)	0.105 (18)*
O3B	−0.11424 (15)	0.65168 (10)	0.14528 (13)	0.0270 (5)
N1B	−0.14367 (18)	0.64547 (12)	0.27942 (17)	0.0232 (5)
HN1B	−0.112 (2)	0.6397 (17)	0.3412 (13)	0.041 (10)*
C1B	−0.4164 (2)	0.72744 (16)	0.2624 (2)	0.0314 (7)
H1B	−0.4580	0.7045	0.2082	0.038*
C2B	−0.4425 (3)	0.79193 (17)	0.2813 (2)	0.0379 (8)
H2B	−0.5026	0.8127	0.2405	0.045*
C3B	−0.3814 (3)	0.82683 (16)	0.3594 (2)	0.0366 (8)
H3B	−0.3989	0.8715	0.3719	0.044*
C4B	−0.2949 (3)	0.79557 (16)	0.4189 (2)	0.0354 (8)
H4B	−0.2529	0.8189	0.4727	0.042*
C5B	−0.2689 (2)	0.73009 (15)	0.4003 (2)	0.0286 (7)
H5B	−0.2093	0.7090	0.4414	0.034*
C6B	−0.3299 (2)	0.69570 (14)	0.32204 (19)	0.0241 (6)
C7B	−0.3057 (2)	0.62345 (15)	0.30217 (19)	0.0249 (6)
H7I	−0.3702	0.5979	0.2751	0.030*
H7J	−0.2658	0.6012	0.3614	0.030*
C8B	−0.2457 (2)	0.61938 (14)	0.23556 (19)	0.0220 (6)
H8B	−0.2811	0.6479	0.1798	0.026*
C9B	−0.2459 (2)	0.54571 (15)	0.2046 (2)	0.0242 (6)
C10B	−0.0818 (2)	0.65723 (14)	0.2319 (2)	0.0248 (6)
C11B	0.0260 (2)	0.67602 (15)	0.2880 (2)	0.0270 (7)
H11B	0.0288	0.6849	0.3529	0.032*
C12B	0.0970 (2)	0.61580 (16)	0.2913 (2)	0.0342 (7)
H12I	0.0725	0.5749	0.3147	0.041*
H12J	0.0965	0.6059	0.2280	0.041*
C13B	0.2057 (2)	0.63242 (16)	0.3548 (2)	0.0361 (8)
H13I	0.2070	0.6376	0.4193	0.043*
H13J	0.2511	0.5941	0.3537	0.043*
C14B	0.2458 (2)	0.69762 (17)	0.3254 (2)	0.0316 (7)
H14B	0.2468	0.6893	0.2616	0.038*
C15B	0.1719 (2)	0.75633 (16)	0.3175 (2)	0.0356 (8)
H15I	0.1963	0.7969	0.2934	0.043*
H15J	0.1712	0.7675	0.3801	0.043*
C16B	0.0632 (2)	0.73996 (16)	0.2538 (2)	0.0332 (7)
H16I	0.0177	0.7786	0.2534	0.040*
H16J	0.0619	0.7329	0.1897	0.040*
C17B	0.3558 (2)	0.71495 (19)	0.3867 (2)	0.0428 (9)
H17B	0.3739	0.7588	0.3634	0.051*
C18B	0.3687 (3)	0.7256 (2)	0.4893 (2)	0.0569 (11)
H18I	0.3565	0.6825	0.5158	0.085*
H18J	0.3198	0.7597	0.4941	0.085*
H18K	0.4380	0.7412	0.5234	0.085*
C19B	0.4309 (3)	0.6619 (2)	0.3788 (3)	0.0535 (10)
H19I	0.4198	0.6193	0.4069	0.080*
H19J	0.5004	0.6780	0.4112	0.080*
H19K	0.4209	0.6543	0.3133	0.080*
O1C	0.04299 (15)	0.44772 (11)	0.37335 (13)	0.0308 (5)
O2C	0.21337 (17)	0.44630 (13)	0.43949 (15)	0.0411 (6)
HO2C	0.207 (3)	0.444 (2)	0.3787 (15)	0.070 (13)*
O3C	−0.00117 (16)	0.33903 (10)	0.51650 (15)	0.0338 (5)
N1C	0.01385 (19)	0.45147 (12)	0.53748 (16)	0.0243 (5)
HN1C	−0.016 (2)	0.4942 (11)	0.527 (2)	0.029 (8)*
C1C	0.2428 (3)	0.56600 (18)	0.7503 (3)	0.0436 (9)
H1C	0.2677	0.6017	0.7224	0.052*
C2C	0.2559 (3)	0.5687 (2)	0.8456 (3)	0.0534 (11)
H2C	0.2916	0.6060	0.8817	0.064*
C3C	0.2190 (3)	0.5196 (2)	0.8868 (3)	0.0576 (11)
H3C	0.2263	0.5232	0.9504	0.069*
C4C	0.1712 (3)	0.4651 (2)	0.8357 (2)	0.0563 (11)
H4C	0.1463	0.4298	0.8644	0.068*
C5C	0.1583 (3)	0.46028 (19)	0.7412 (2)	0.0446 (9)
H5C	0.1249	0.4217	0.7068	0.054*
C6C	0.1932 (2)	0.51051 (18)	0.6977 (2)	0.0354 (8)
C7C	0.1818 (2)	0.50885 (17)	0.5955 (2)	0.0327 (7)
H7CM	0.1496	0.5519	0.5663	0.039*
H7CN	0.2504	0.5069	0.5909	0.039*
C8C	0.1191 (2)	0.44961 (16)	0.54051 (19)	0.0261 (6)
H8C	0.1506	0.4065	0.5720	0.031*
C9C	0.1211 (2)	0.44808 (15)	0.4422 (2)	0.0274 (7)
C10C	−0.0422 (2)	0.39503 (15)	0.52003 (19)	0.0253 (6)
C11C	−0.1536 (2)	0.40073 (15)	0.50325 (18)	0.0258 (7)
H11C	−0.1770	0.3547	0.5150	0.031*
C12C	−0.1850 (2)	0.45091 (17)	0.5647 (2)	0.0316 (7)
H12M	−0.1492	0.4397	0.6308	0.038*
H12N	−0.1656	0.4977	0.5536	0.038*
C13C	−0.2999 (2)	0.44710 (18)	0.5425 (2)	0.0351 (8)
H13M	−0.3177	0.4012	0.5585	0.042*
H13N	−0.3196	0.4804	0.5816	0.042*
C14C	−0.3602 (2)	0.46156 (17)	0.4410 (2)	0.0321 (7)
H14C	−0.3417	0.5088	0.4287	0.039*
C15C	−0.3254 (2)	0.41472 (18)	0.3786 (2)	0.0369 (8)
H15M	−0.3457	0.3675	0.3861	0.044*
H15N	−0.3603	0.4281	0.3132	0.044*
C16C	−0.2107 (2)	0.41713 (18)	0.4005 (2)	0.0335 (8)
H16M	−0.1910	0.4630	0.3862	0.040*
H16N	−0.1915	0.3838	0.3612	0.040*
C17C	−0.4762 (2)	0.4618 (2)	0.4195 (2)	0.0440 (9)
H17C	−0.4902	0.4969	0.4606	0.053*
C18C	−0.5335 (3)	0.4844 (2)	0.3187 (3)	0.0553 (11)
H18M	−0.5285	0.4486	0.2760	0.083*
H18N	−0.5032	0.5264	0.3059	0.083*
H18P	−0.6053	0.4923	0.3101	0.083*
C19C	−0.5195 (3)	0.3964 (2)	0.4385 (4)	0.0749 (14)
H19M	−0.5923	0.4022	0.4274	0.112*
H19N	−0.4844	0.3831	0.5033	0.112*
H19P	−0.5102	0.3609	0.3975	0.112*
O1D	−0.18376 (15)	0.38516 (10)	0.17923 (13)	0.0273 (5)
O2D	−0.35411 (16)	0.39201 (11)	0.11892 (16)	0.0382 (5)
HO2D	−0.336 (3)	0.4370 (11)	0.139 (2)	0.063 (12)*
O3D	−0.18841 (14)	0.24624 (10)	0.28940 (13)	0.0256 (4)
N1D	−0.18444 (18)	0.24963 (12)	0.14512 (16)	0.0225 (5)
HN1D	−0.144 (2)	0.2499 (16)	0.1089 (18)	0.030 (8)*
C1D	−0.4500 (2)	0.18168 (16)	−0.0122 (2)	0.0313 (7)
H1D	−0.4840	0.2075	0.0204	0.038*
C2D	−0.4843 (2)	0.11683 (17)	−0.0433 (2)	0.0360 (7)
H2D	−0.5414	0.0985	−0.0316	0.043*
C3D	−0.4362 (3)	0.07918 (18)	−0.0907 (2)	0.0421 (9)
H3D	−0.4607	0.0351	−0.1125	0.051*
C4D	−0.3518 (3)	0.10526 (17)	−0.1069 (2)	0.0388 (8)
H4D	−0.3180	0.0789	−0.1392	0.047*
C5D	−0.3171 (2)	0.17015 (16)	−0.0756 (2)	0.0329 (7)
H5D	−0.2594	0.1880	−0.0866	0.039*
C6D	−0.3661 (2)	0.20907 (15)	−0.02839 (18)	0.0251 (6)
C7D	−0.3299 (2)	0.28009 (15)	0.00509 (18)	0.0248 (6)
H7DQ	−0.3884	0.3118	−0.0163	0.030*
H7DR	−0.2795	0.2947	−0.0230	0.030*
C8D	−0.2813 (2)	0.28467 (15)	0.11121 (18)	0.0232 (6)
H8D	−0.3283	0.2630	0.1393	0.028*
C9D	−0.2670 (2)	0.35912 (15)	0.14078 (19)	0.0244 (6)
C10D	−0.1399 (2)	0.23607 (14)	0.23494 (19)	0.0226 (6)
C11D	−0.0321 (2)	0.21081 (15)	0.26960 (19)	0.0250 (6)
H11D	−0.0180	0.1933	0.3339	0.030*
C12D	−0.0093 (2)	0.15309 (15)	0.2134 (2)	0.0285 (7)
H12Q	−0.0216	0.1685	0.1492	0.034*
H12R	−0.0548	0.1141	0.2110	0.034*
C13D	0.1017 (2)	0.13120 (15)	0.2588 (2)	0.0286 (7)
H13Q	0.1129	0.1145	0.3223	0.034*
H13R	0.1163	0.0933	0.2228	0.034*
C14D	0.1744 (2)	0.19011 (15)	0.2632 (2)	0.0278 (7)
H14D	0.1591	0.2067	0.1983	0.033*
C15D	0.1517 (2)	0.24840 (16)	0.3181 (2)	0.0319 (7)
H15Q	0.1969	0.2872	0.3187	0.038*
H15R	0.1664	0.2337	0.3830	0.038*
C16D	0.0401 (2)	0.27181 (15)	0.2769 (2)	0.0281 (7)
H16Q	0.0271	0.2915	0.2146	0.034*
H16R	0.0271	0.3075	0.3168	0.034*
C17D	0.2861 (2)	0.16681 (16)	0.2990 (2)	0.0337 (7)
H17D	0.2892	0.1247	0.2637	0.040*
C18D	0.3574 (3)	0.2185 (2)	0.2783 (3)	0.0559 (10)
H18Q	0.3590	0.2604	0.3134	0.084*
H18R	0.3327	0.2288	0.2118	0.084*
H18S	0.4262	0.1994	0.2964	0.084*
C19D	0.3261 (3)	0.1474 (2)	0.4010 (2)	0.0473 (9)
H19Q	0.3926	0.1253	0.4159	0.071*
H19R	0.2784	0.1160	0.4139	0.071*
H19S	0.3333	0.1884	0.4390	0.071*
O4	0.10227 (16)	0.73167 (11)	0.54298 (14)	0.0275 (5)
HO4A	0.061 (2)	0.7705 (14)	0.516 (2)	0.049 (10)*
HO4B	0.136 (4)	0.730 (3)	0.6089 (15)	0.12 (2)*
HO4C	0.051 (3)	0.6968 (17)	0.532 (3)	0.076 (14)*
O5	0.03395 (17)	0.15067 (11)	−0.02283 (15)	0.0288 (5)
HO5A	−0.006 (2)	0.1901 (14)	−0.021 (3)	0.054 (11)*
HO5B	0.060 (3)	0.159 (2)	−0.072 (2)	0.094 (16)*
HO5C	−0.003 (3)	0.1080 (13)	−0.031 (2)	0.055 (11)*
Cl1	−0.04404 (6)	0.61402 (4)	0.49921 (5)	0.02937 (17)
Cl2	−0.07094 (6)	0.27751 (4)	−0.00425 (5)	0.02868 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0263 (13)	0.0662 (17)	0.0321 (12)	−0.0028 (12)	0.0081 (11)	−0.0076 (12)
O2A	0.0239 (12)	0.0323 (12)	0.0271 (11)	−0.0028 (9)	0.0102 (9)	−0.0013 (9)
O3A	0.0330 (12)	0.0197 (11)	0.0340 (12)	−0.0024 (9)	0.0127 (10)	−0.0017 (9)
N1A	0.0302 (15)	0.0210 (13)	0.0240 (12)	−0.0007 (11)	0.0123 (11)	−0.0010 (10)
C1A	0.0308 (19)	0.050 (2)	0.0349 (18)	−0.0010 (16)	0.0083 (16)	−0.0041 (16)
C2A	0.035 (2)	0.063 (3)	0.058 (2)	−0.0012 (18)	0.0262 (19)	0.000 (2)
C3A	0.056 (2)	0.035 (2)	0.070 (3)	−0.0008 (17)	0.047 (2)	−0.0057 (18)
C4A	0.071 (3)	0.036 (2)	0.058 (2)	−0.0175 (19)	0.040 (2)	−0.0197 (18)
C5A	0.047 (2)	0.0318 (18)	0.054 (2)	−0.0117 (16)	0.0288 (19)	−0.0107 (16)
C6A	0.0293 (18)	0.0245 (16)	0.0394 (18)	0.0013 (13)	0.0160 (15)	0.0038 (14)
C7A	0.0279 (17)	0.0292 (17)	0.0290 (15)	0.0034 (13)	0.0120 (14)	0.0051 (13)
C8A	0.0278 (17)	0.0277 (16)	0.0277 (15)	−0.0024 (13)	0.0130 (14)	−0.0002 (13)
C9A	0.0287 (18)	0.0276 (17)	0.0293 (16)	0.0005 (13)	0.0105 (15)	0.0023 (14)
C10A	0.0325 (17)	0.0220 (16)	0.0211 (14)	0.0004 (13)	0.0140 (13)	−0.0003 (12)
C11A	0.0288 (17)	0.0233 (16)	0.0227 (14)	0.0037 (13)	0.0088 (13)	0.0035 (12)
C12A	0.0328 (18)	0.0262 (16)	0.0248 (15)	0.0043 (13)	0.0103 (14)	−0.0026 (13)
C13A	0.0355 (18)	0.0264 (16)	0.0244 (15)	−0.0026 (14)	0.0080 (14)	−0.0006 (13)
C14A	0.0353 (19)	0.0229 (16)	0.0292 (16)	−0.0011 (14)	0.0091 (14)	0.0060 (13)
C15A	0.0297 (17)	0.0346 (18)	0.0327 (17)	−0.0002 (14)	0.0136 (14)	−0.0018 (14)
C16A	0.0317 (18)	0.0338 (18)	0.0273 (16)	−0.0007 (14)	0.0125 (14)	−0.0012 (14)
C17A	0.0305 (18)	0.0331 (18)	0.0331 (17)	−0.0076 (14)	0.0066 (15)	0.0040 (14)
C18A	0.033 (2)	0.044 (2)	0.049 (2)	−0.0093 (16)	0.0128 (17)	0.0002 (17)
C19A	0.033 (2)	0.048 (2)	0.052 (2)	−0.0054 (17)	0.0031 (17)	0.0167 (18)
O1B	0.0296 (13)	0.0254 (12)	0.0469 (13)	0.0027 (10)	0.0014 (11)	−0.0122 (10)
O2B	0.0213 (11)	0.0214 (11)	0.0332 (11)	0.0021 (9)	0.0065 (9)	−0.0002 (9)
O3B	0.0282 (12)	0.0298 (11)	0.0246 (11)	0.0002 (9)	0.0111 (9)	−0.0004 (9)
N1B	0.0229 (14)	0.0231 (13)	0.0224 (13)	−0.0015 (10)	0.0063 (11)	−0.0001 (11)
C1B	0.0331 (18)	0.0327 (17)	0.0275 (16)	0.0032 (14)	0.0093 (14)	0.0018 (14)
C2B	0.046 (2)	0.0333 (19)	0.0343 (18)	0.0116 (16)	0.0133 (16)	0.0031 (15)
C3B	0.051 (2)	0.0218 (16)	0.0402 (19)	0.0066 (15)	0.0202 (18)	−0.0035 (14)
C4B	0.044 (2)	0.0286 (18)	0.0336 (17)	−0.0036 (15)	0.0140 (16)	−0.0052 (14)
C5B	0.0305 (17)	0.0266 (16)	0.0283 (15)	0.0001 (13)	0.0097 (14)	−0.0022 (13)
C6B	0.0279 (16)	0.0240 (15)	0.0259 (15)	−0.0012 (13)	0.0162 (14)	0.0012 (12)
C7B	0.0259 (16)	0.0236 (15)	0.0265 (14)	−0.0007 (12)	0.0106 (13)	0.0010 (12)
C8B	0.0221 (15)	0.0198 (14)	0.0240 (14)	0.0008 (12)	0.0082 (12)	−0.0028 (12)
C9B	0.0241 (17)	0.0229 (15)	0.0234 (15)	0.0010 (13)	0.0054 (13)	0.0015 (12)
C10B	0.0293 (17)	0.0184 (15)	0.0274 (16)	−0.0011 (12)	0.0108 (14)	0.0003 (12)
C11B	0.0243 (16)	0.0286 (16)	0.0264 (15)	−0.0049 (13)	0.0065 (13)	−0.0017 (13)
C12B	0.0309 (18)	0.0240 (16)	0.0436 (18)	−0.0002 (14)	0.0079 (15)	−0.0017 (15)
C13B	0.0313 (18)	0.0318 (18)	0.0410 (18)	0.0038 (14)	0.0073 (15)	0.0033 (15)
C14B	0.0268 (17)	0.0385 (19)	0.0292 (16)	−0.0054 (14)	0.0093 (14)	−0.0035 (14)
C15B	0.0345 (19)	0.0250 (17)	0.0423 (19)	−0.0054 (14)	0.0068 (16)	0.0017 (14)
C16B	0.0284 (18)	0.0264 (17)	0.0390 (18)	−0.0013 (14)	0.0044 (15)	0.0001 (14)
C17B	0.0262 (19)	0.046 (2)	0.048 (2)	−0.0095 (16)	0.0036 (16)	0.0010 (17)
C18B	0.042 (2)	0.064 (3)	0.049 (2)	−0.003 (2)	−0.0039 (19)	−0.015 (2)
C19B	0.030 (2)	0.075 (3)	0.052 (2)	0.0021 (19)	0.0094 (18)	0.001 (2)
O1C	0.0279 (12)	0.0360 (12)	0.0265 (11)	0.0021 (10)	0.0067 (10)	−0.0022 (10)
O2C	0.0304 (13)	0.0636 (17)	0.0315 (12)	0.0033 (11)	0.0137 (11)	0.0027 (12)
O3C	0.0324 (13)	0.0225 (11)	0.0425 (13)	0.0014 (10)	0.0080 (10)	−0.0020 (10)
N1C	0.0253 (14)	0.0199 (13)	0.0265 (13)	0.0004 (11)	0.0073 (11)	0.0019 (11)
C1C	0.034 (2)	0.0359 (19)	0.052 (2)	0.0075 (15)	0.0029 (17)	−0.0149 (17)
C2C	0.041 (2)	0.051 (2)	0.050 (2)	0.0130 (19)	−0.0073 (19)	−0.030 (2)
C3C	0.066 (3)	0.060 (3)	0.033 (2)	0.024 (2)	0.001 (2)	−0.007 (2)
C4C	0.081 (3)	0.050 (3)	0.0304 (19)	0.019 (2)	0.010 (2)	0.0008 (18)
C5C	0.058 (2)	0.037 (2)	0.0302 (17)	0.0042 (18)	0.0045 (17)	−0.0048 (16)
C6C	0.0231 (17)	0.0384 (19)	0.0346 (17)	0.0079 (15)	−0.0027 (14)	−0.0128 (15)
C7C	0.0284 (17)	0.0287 (17)	0.0369 (18)	−0.0060 (14)	0.0062 (15)	−0.0034 (14)
C8C	0.0273 (17)	0.0263 (16)	0.0237 (14)	0.0009 (13)	0.0075 (13)	−0.0018 (13)
C9C	0.0282 (18)	0.0218 (15)	0.0327 (16)	0.0004 (13)	0.0113 (15)	−0.0001 (13)
C10C	0.0301 (17)	0.0245 (16)	0.0197 (14)	0.0010 (13)	0.0065 (13)	0.0017 (12)
C11C	0.0293 (17)	0.0257 (16)	0.0213 (14)	−0.0001 (13)	0.0075 (13)	0.0024 (12)
C12C	0.0305 (18)	0.0385 (18)	0.0232 (15)	0.0048 (15)	0.0062 (14)	−0.0011 (14)
C13C	0.0333 (19)	0.043 (2)	0.0310 (17)	0.0020 (15)	0.0143 (15)	0.0006 (15)
C14C	0.0280 (18)	0.0362 (18)	0.0319 (16)	−0.0009 (14)	0.0102 (14)	0.0081 (15)
C15C	0.0295 (19)	0.049 (2)	0.0278 (17)	−0.0003 (15)	0.0041 (15)	−0.0025 (15)
C16C	0.0303 (18)	0.046 (2)	0.0222 (15)	0.0015 (15)	0.0060 (14)	−0.0033 (14)
C17C	0.0293 (19)	0.061 (2)	0.045 (2)	−0.0009 (17)	0.0173 (16)	0.0115 (19)
C18C	0.031 (2)	0.079 (3)	0.050 (2)	0.002 (2)	0.0071 (18)	0.013 (2)
C19C	0.047 (3)	0.074 (3)	0.104 (4)	−0.005 (2)	0.027 (3)	0.024 (3)
O1D	0.0234 (12)	0.0247 (11)	0.0301 (11)	−0.0024 (9)	0.0047 (10)	−0.0021 (9)
O2D	0.0227 (12)	0.0275 (12)	0.0539 (14)	0.0036 (10)	0.0001 (11)	−0.0138 (11)
O3D	0.0239 (11)	0.0306 (11)	0.0232 (10)	0.0022 (9)	0.0094 (9)	−0.0004 (9)
N1D	0.0260 (14)	0.0226 (12)	0.0191 (12)	0.0044 (10)	0.0081 (11)	0.0030 (10)
C1D	0.0361 (19)	0.0293 (16)	0.0257 (16)	−0.0029 (14)	0.0073 (14)	−0.0002 (13)
C2D	0.0334 (18)	0.0336 (18)	0.0326 (17)	−0.0068 (16)	0.0010 (15)	0.0054 (15)
C3D	0.045 (2)	0.0316 (19)	0.0354 (18)	−0.0058 (16)	−0.0047 (17)	−0.0038 (15)
C4D	0.046 (2)	0.0292 (18)	0.0336 (17)	0.0054 (16)	0.0038 (16)	−0.0086 (15)
C5D	0.0307 (18)	0.0335 (18)	0.0307 (17)	0.0002 (14)	0.0058 (15)	−0.0004 (14)
C6D	0.0277 (17)	0.0254 (15)	0.0172 (13)	−0.0012 (13)	0.0015 (12)	0.0011 (12)
C7D	0.0270 (16)	0.0216 (14)	0.0235 (14)	0.0002 (13)	0.0059 (12)	0.0032 (13)
C8D	0.0228 (15)	0.0207 (15)	0.0237 (14)	−0.0007 (12)	0.0052 (12)	0.0001 (12)
C9D	0.0269 (17)	0.0246 (16)	0.0224 (14)	0.0048 (13)	0.0094 (13)	0.0023 (12)
C10D	0.0238 (16)	0.0158 (14)	0.0270 (15)	−0.0020 (12)	0.0071 (13)	−0.0042 (12)
C11D	0.0241 (16)	0.0275 (16)	0.0218 (14)	0.0065 (12)	0.0058 (13)	0.0021 (12)
C12D	0.0292 (17)	0.0253 (16)	0.0305 (16)	0.0035 (13)	0.0096 (14)	−0.0035 (13)
C13D	0.0289 (17)	0.0243 (16)	0.0300 (16)	0.0054 (13)	0.0070 (14)	−0.0046 (13)
C14D	0.0237 (16)	0.0288 (17)	0.0282 (16)	0.0036 (13)	0.0055 (13)	0.0009 (13)
C15D	0.0261 (17)	0.0268 (16)	0.0371 (17)	0.0033 (13)	0.0037 (14)	−0.0022 (14)
C16D	0.0260 (16)	0.0227 (15)	0.0327 (16)	0.0025 (13)	0.0065 (13)	−0.0047 (13)
C17D	0.0264 (17)	0.0309 (18)	0.0406 (18)	0.0059 (14)	0.0076 (15)	−0.0027 (14)
C18D	0.031 (2)	0.049 (2)	0.087 (3)	0.0058 (17)	0.020 (2)	0.009 (2)
C19D	0.037 (2)	0.054 (2)	0.0375 (19)	0.0167 (18)	−0.0037 (16)	−0.0057 (17)
O4	0.0314 (13)	0.0269 (12)	0.0232 (11)	−0.0003 (10)	0.0080 (10)	0.0011 (10)
O5	0.0364 (13)	0.0217 (11)	0.0337 (12)	0.0015 (10)	0.0189 (11)	0.0004 (10)
Cl1	0.0351 (4)	0.0228 (4)	0.0262 (4)	−0.0002 (3)	0.0055 (3)	−0.0006 (3)
Cl2	0.0337 (4)	0.0221 (4)	0.0333 (4)	0.0015 (3)	0.0156 (3)	0.0008 (3)

Geometric parameters (Å, º)

O1A—C9A	1.239 (4)	O3C—C10C	1.252 (4)
O2A—C9A	1.291 (4)	N1C—C10C	1.332 (4)
O2A—HO2A	0.949 (19)	N1C—C8C	1.460 (4)
O3A—C10A	1.266 (3)	N1C—HN1C	0.927 (17)
N1A—C10A	1.329 (4)	C1C—C6C	1.392 (5)
N1A—C8A	1.450 (4)	C1C—C2C	1.413 (5)
N1A—HN1A	0.944 (18)	C1C—H1C	0.9500
C1A—C2A	1.379 (5)	C2C—C3C	1.351 (6)
C1A—C6A	1.383 (4)	C2C—H2C	0.9500
C1A—H1A	0.9500	C3C—C4C	1.361 (6)
C2A—C3A	1.376 (5)	C3C—H3C	0.9500
C2A—H2A	0.9500	C4C—C5C	1.404 (5)
C3A—C4A	1.368 (5)	C4C—H4C	0.9500
C3A—H3A	0.9500	C5C—C6C	1.374 (5)
C4A—C5A	1.404 (4)	C5C—H5C	0.9500
C4A—H4A	0.9500	C6C—C7C	1.524 (4)
C5A—C6A	1.378 (5)	C7C—C8C	1.525 (4)
C5A—H5A	0.9500	C7C—H7CM	0.9900
C6A—C7A	1.517 (4)	C7C—H7CN	0.9900
C7A—C8A	1.536 (4)	C8C—C9C	1.522 (4)
C7A—H7E	0.9900	C8C—H8C	1.0000
C7A—H7F	0.9900	C10C—C11C	1.495 (4)
C8A—C9A	1.522 (4)	C11C—C12C	1.532 (4)
C8A—H8A	1.0000	C11C—C16C	1.537 (4)
C10A—C11A	1.502 (4)	C11C—H11C	1.0000
C11A—C12A	1.531 (4)	C12C—C13C	1.528 (4)
C11A—C16A	1.541 (4)	C12C—H12M	0.9900
C11A—H11A	1.0000	C12C—H12N	0.9900
C12A—C13A	1.526 (4)	C13C—C14C	1.522 (4)
C12A—H12E	0.9900	C13C—H13M	0.9900
C12A—H12F	0.9900	C13C—H13N	0.9900
C13A—C14A	1.529 (4)	C14C—C15C	1.527 (4)
C13A—H13E	0.9900	C14C—C17C	1.542 (4)
C13A—H13F	0.9900	C14C—H14C	1.0000
C14A—C15A	1.522 (4)	C15C—C16C	1.524 (4)
C14A—C17A	1.544 (4)	C15C—H15M	0.9900
C14A—H14A	1.0000	C15C—H15N	0.9900
C15A—C16A	1.532 (4)	C16C—H16M	0.9900
C15A—H15E	0.9900	C16C—H16N	0.9900
C15A—H15F	0.9900	C17C—C19C	1.495 (5)
C16A—H16E	0.9900	C17C—C18C	1.543 (5)
C16A—H16F	0.9900	C17C—H17C	1.0000
C17A—C19A	1.535 (5)	C18C—H18M	0.9800
C17A—C18A	1.537 (4)	C18C—H18N	0.9800
C17A—H17A	1.0000	C18C—H18P	0.9800
C18A—H18E	0.9800	C19C—H19M	0.9800
C18A—H18F	0.9800	C19C—H19N	0.9800
C18A—H18G	0.9800	C19C—H19P	0.9800
C19A—H19E	0.9800	O1D—C9D	1.223 (3)
C19A—H19F	0.9800	O2D—C9D	1.317 (3)
C19A—H19G	0.9800	O2D—HO2D	0.944 (19)
O1B—C9B	1.233 (3)	O3D—C10D	1.265 (3)
O2B—C9B	1.297 (3)	N1D—C10D	1.331 (4)
O2B—HO2B	0.948 (19)	N1D—C8D	1.448 (4)
O3B—C10B	1.254 (3)	N1D—HN1D	0.921 (17)
N1B—C10B	1.334 (4)	C1D—C2D	1.388 (4)
N1B—C8B	1.446 (4)	C1D—C6D	1.392 (4)
N1B—HN1B	0.905 (18)	C1D—H1D	0.9500
C1B—C2B	1.378 (4)	C2D—C3D	1.368 (5)
C1B—C6B	1.388 (4)	C2D—H2D	0.9500
C1B—H1B	0.9500	C3D—C4D	1.389 (5)
C2B—C3B	1.391 (5)	C3D—H3D	0.9500
C2B—H2B	0.9500	C4D—C5D	1.391 (5)
C3B—C4B	1.384 (5)	C4D—H4D	0.9500
C3B—H3B	0.9500	C5D—C6D	1.389 (4)
C4B—C5B	1.394 (4)	C5D—H5D	0.9500
C4B—H4B	0.9500	C6D—C7D	1.514 (4)
C5B—C6B	1.387 (4)	C7D—C8D	1.538 (4)
C5B—H5B	0.9500	C7D—H7DQ	0.9900
C6B—C7B	1.516 (4)	C7D—H7DR	0.9900
C7B—C8B	1.537 (4)	C8D—C9D	1.525 (4)
C7B—H7I	0.9900	C8D—H8D	1.0000
C7B—H7J	0.9900	C10D—C11D	1.501 (4)
C8B—C9B	1.525 (4)	C11D—C12D	1.526 (4)
C8B—H8B	1.0000	C11D—C16D	1.548 (4)
C10B—C11B	1.502 (4)	C11D—H11D	1.0000
C11B—C16B	1.523 (4)	C12D—C13D	1.528 (4)
C11B—C12B	1.537 (4)	C12D—H12Q	0.9900
C11B—H11B	1.0000	C12D—H12R	0.9900
C12B—C13B	1.532 (4)	C13D—C14D	1.528 (4)
C12B—H12I	0.9900	C13D—H13Q	0.9900
C12B—H12J	0.9900	C13D—H13R	0.9900
C13B—C14B	1.530 (4)	C14D—C15D	1.521 (4)
C13B—H13I	0.9900	C14D—C17D	1.538 (4)
C13B—H13J	0.9900	C14D—H14D	1.0000
C14B—C15B	1.528 (4)	C15D—C16D	1.539 (4)
C14B—C17B	1.540 (4)	C15D—H15Q	0.9900
C14B—H14B	1.0000	C15D—H15R	0.9900
C15B—C16B	1.532 (4)	C16D—H16Q	0.9900
C15B—H15I	0.9900	C16D—H16R	0.9900
C15B—H15J	0.9900	C17D—C19D	1.520 (5)
C16B—H16I	0.9900	C17D—C18D	1.535 (5)
C16B—H16J	0.9900	C17D—H17D	1.0000
C17B—C19B	1.516 (5)	C18D—H18Q	0.9800
C17B—C18B	1.539 (5)	C18D—H18R	0.9800
C17B—H17B	1.0000	C18D—H18S	0.9800
C18B—H18I	0.9800	C19D—H19Q	0.9800
C18B—H18J	0.9800	C19D—H19R	0.9800
C18B—H18K	0.9800	C19D—H19S	0.9800
C19B—H19I	0.9800	O4—HO4A	0.960 (18)
C19B—H19J	0.9800	O4—HO4B	0.960 (19)
C19B—H19K	0.9800	O4—HO4C	0.965 (19)
O1C—C9C	1.231 (3)	O5—HO5A	0.960 (18)
O2C—C9C	1.308 (4)	O5—HO5B	0.958 (19)
O2C—HO2C	0.909 (18)	O5—HO5C	0.970 (19)
C9A—O2A—HO2A	111 (3)	C8C—N1C—HN1C	114.5 (19)
C10A—N1A—C8A	120.6 (3)	C6C—C1C—C2C	119.4 (4)
C10A—N1A—HN1A	122 (2)	C6C—C1C—H1C	120.3
C8A—N1A—HN1A	117 (2)	C2C—C1C—H1C	120.3
C2A—C1A—C6A	121.0 (3)	C3C—C2C—C1C	121.7 (4)
C2A—C1A—H1A	119.5	C3C—C2C—H2C	119.1
C6A—C1A—H1A	119.5	C1C—C2C—H2C	119.1
C3A—C2A—C1A	119.8 (3)	C2C—C3C—C4C	119.0 (4)
C3A—C2A—H2A	120.1	C2C—C3C—H3C	120.5
C1A—C2A—H2A	120.1	C4C—C3C—H3C	120.5
C4A—C3A—C2A	119.9 (3)	C3C—C4C—C5C	120.7 (4)
C4A—C3A—H3A	120.1	C3C—C4C—H4C	119.6
C2A—C3A—H3A	120.1	C5C—C4C—H4C	119.6
C3A—C4A—C5A	120.5 (3)	C6C—C5C—C4C	121.0 (4)
C3A—C4A—H4A	119.8	C6C—C5C—H5C	119.5
C5A—C4A—H4A	119.8	C4C—C5C—H5C	119.5
C6A—C5A—C4A	119.5 (3)	C5C—C6C—C1C	118.1 (3)
C6A—C5A—H5A	120.2	C5C—C6C—C7C	124.0 (3)
C4A—C5A—H5A	120.2	C1C—C6C—C7C	117.9 (3)
C5A—C6A—C1A	119.2 (3)	C8C—C7C—C6C	115.0 (3)
C5A—C6A—C7A	121.1 (3)	C8C—C7C—H7CM	108.5
C1A—C6A—C7A	119.6 (3)	C6C—C7C—H7CM	108.5
C6A—C7A—C8A	112.2 (2)	C8C—C7C—H7CN	108.5
C6A—C7A—H7E	109.2	C6C—C7C—H7CN	108.5
C8A—C7A—H7E	109.2	H7CM—C7C—H7CN	107.5
C6A—C7A—H7F	109.2	N1C—C8C—C9C	109.6 (2)
C8A—C7A—H7F	109.2	N1C—C8C—C7C	112.3 (2)
H7E—C7A—H7F	107.9	C9C—C8C—C7C	111.1 (2)
N1A—C8A—C9A	111.9 (2)	N1C—C8C—H8C	107.9
N1A—C8A—C7A	112.0 (2)	C9C—C8C—H8C	107.9
C9A—C8A—C7A	108.9 (2)	C7C—C8C—H8C	107.9
N1A—C8A—H8A	107.9	O1C—C9C—O2C	124.5 (3)
C9A—C8A—H8A	107.9	O1C—C9C—C8C	122.5 (3)
C7A—C8A—H8A	107.9	O2C—C9C—C8C	113.0 (3)
O1A—C9A—O2A	124.4 (3)	O3C—C10C—N1C	119.6 (3)
O1A—C9A—C8A	118.7 (3)	O3C—C10C—C11C	121.7 (3)
O2A—C9A—C8A	116.8 (3)	N1C—C10C—C11C	118.6 (3)
O3A—C10A—N1A	118.7 (3)	C10C—C11C—C12C	116.6 (2)
O3A—C10A—C11A	120.7 (3)	C10C—C11C—C16C	109.5 (2)
N1A—C10A—C11A	120.5 (3)	C12C—C11C—C16C	109.9 (2)
C10A—C11A—C12A	115.9 (2)	C10C—C11C—H11C	106.8
C10A—C11A—C16A	108.6 (2)	C12C—C11C—H11C	106.8
C12A—C11A—C16A	109.9 (2)	C16C—C11C—H11C	106.8
C10A—C11A—H11A	107.3	C13C—C12C—C11C	109.7 (3)
C12A—C11A—H11A	107.3	C13C—C12C—H12M	109.7
C16A—C11A—H11A	107.3	C11C—C12C—H12M	109.7
C13A—C12A—C11A	110.8 (2)	C13C—C12C—H12N	109.7
C13A—C12A—H12E	109.5	C11C—C12C—H12N	109.7
C11A—C12A—H12E	109.5	H12M—C12C—H12N	108.2
C13A—C12A—H12F	109.5	C14C—C13C—C12C	112.8 (2)
C11A—C12A—H12F	109.5	C14C—C13C—H13M	109.0
H12E—C12A—H12F	108.1	C12C—C13C—H13M	109.0
C12A—C13A—C14A	112.4 (2)	C14C—C13C—H13N	109.0
C12A—C13A—H13E	109.1	C12C—C13C—H13N	109.0
C14A—C13A—H13E	109.1	H13M—C13C—H13N	107.8
C12A—C13A—H13F	109.1	C13C—C14C—C15C	110.3 (3)
C14A—C13A—H13F	109.1	C13C—C14C—C17C	113.0 (2)
H13E—C13A—H13F	107.9	C15C—C14C—C17C	114.2 (3)
C15A—C14A—C13A	110.1 (2)	C13C—C14C—H14C	106.2
C15A—C14A—C17A	114.7 (3)	C15C—C14C—H14C	106.2
C13A—C14A—C17A	112.7 (2)	C17C—C14C—H14C	106.2
C15A—C14A—H14A	106.2	C16C—C15C—C14C	112.6 (3)
C13A—C14A—H14A	106.2	C16C—C15C—H15M	109.1
C17A—C14A—H14A	106.2	C14C—C15C—H15M	109.1
C14A—C15A—C16A	111.2 (3)	C16C—C15C—H15N	109.1
C14A—C15A—H15E	109.4	C14C—C15C—H15N	109.1
C16A—C15A—H15E	109.4	H15M—C15C—H15N	107.8
C14A—C15A—H15F	109.4	C15C—C16C—C11C	110.7 (2)
C16A—C15A—H15F	109.4	C15C—C16C—H16M	109.5
H15E—C15A—H15F	108.0	C11C—C16C—H16M	109.5
C15A—C16A—C11A	110.5 (2)	C15C—C16C—H16N	109.5
C15A—C16A—H16E	109.5	C11C—C16C—H16N	109.5
C11A—C16A—H16E	109.5	H16M—C16C—H16N	108.1
C15A—C16A—H16F	109.5	C19C—C17C—C18C	109.8 (3)
C11A—C16A—H16F	109.5	C19C—C17C—C14C	115.1 (3)
H16E—C16A—H16F	108.1	C18C—C17C—C14C	111.1 (3)
C19A—C17A—C18A	109.0 (3)	C19C—C17C—H17C	106.8
C19A—C17A—C14A	114.3 (3)	C18C—C17C—H17C	106.8
C18A—C17A—C14A	111.6 (2)	C14C—C17C—H17C	106.8
C19A—C17A—H17A	107.2	C17C—C18C—H18M	109.5
C18A—C17A—H17A	107.2	C17C—C18C—H18N	109.5
C14A—C17A—H17A	107.2	H18M—C18C—H18N	109.5
C17A—C18A—H18E	109.5	C17C—C18C—H18P	109.5
C17A—C18A—H18F	109.5	H18M—C18C—H18P	109.5
H18E—C18A—H18F	109.5	H18N—C18C—H18P	109.5
C17A—C18A—H18G	109.5	C17C—C19C—H19M	109.5
H18E—C18A—H18G	109.5	C17C—C19C—H19N	109.5
H18F—C18A—H18G	109.5	H19M—C19C—H19N	109.5
C17A—C19A—H19E	109.5	C17C—C19C—H19P	109.5
C17A—C19A—H19F	109.5	H19M—C19C—H19P	109.5
H19E—C19A—H19F	109.5	H19N—C19C—H19P	109.5
C17A—C19A—H19G	109.5	C9D—O2D—HO2D	105 (2)
H19E—C19A—H19G	109.5	C10D—N1D—C8D	120.9 (2)
H19F—C19A—H19G	109.5	C10D—N1D—HN1D	117.6 (19)
C9B—O2B—HO2B	115 (3)	C8D—N1D—HN1D	118.3 (19)
C10B—N1B—C8B	122.1 (2)	C2D—C1D—C6D	120.4 (3)
C10B—N1B—HN1B	115 (2)	C2D—C1D—H1D	119.8
C8B—N1B—HN1B	120 (2)	C6D—C1D—H1D	119.8
C2B—C1B—C6B	120.6 (3)	C3D—C2D—C1D	120.4 (3)
C2B—C1B—H1B	119.7	C3D—C2D—H2D	119.8
C6B—C1B—H1B	119.7	C1D—C2D—H2D	119.8
C1B—C2B—C3B	120.5 (3)	C2D—C3D—C4D	120.2 (3)
C1B—C2B—H2B	119.8	C2D—C3D—H3D	119.9
C3B—C2B—H2B	119.8	C4D—C3D—H3D	119.9
C4B—C3B—C2B	119.1 (3)	C3D—C4D—C5D	119.6 (3)
C4B—C3B—H3B	120.4	C3D—C4D—H4D	120.2
C2B—C3B—H3B	120.4	C5D—C4D—H4D	120.2
C3B—C4B—C5B	120.4 (3)	C6D—C5D—C4D	120.7 (3)
C3B—C4B—H4B	119.8	C6D—C5D—H5D	119.7
C5B—C4B—H4B	119.8	C4D—C5D—H5D	119.7
C6B—C5B—C4B	120.1 (3)	C5D—C6D—C1D	118.8 (3)
C6B—C5B—H5B	119.9	C5D—C6D—C7D	121.2 (3)
C4B—C5B—H5B	119.9	C1D—C6D—C7D	120.0 (3)
C1B—C6B—C5B	119.2 (3)	C6D—C7D—C8D	112.8 (2)
C1B—C6B—C7B	119.6 (3)	C6D—C7D—H7DQ	109.0
C5B—C6B—C7B	121.2 (3)	C8D—C7D—H7DQ	109.0
C6B—C7B—C8B	113.3 (2)	C6D—C7D—H7DR	109.0
C6B—C7B—H7I	108.9	C8D—C7D—H7DR	109.0
C8B—C7B—H7I	108.9	H7DQ—C7D—H7DR	107.8
C6B—C7B—H7J	108.9	N1D—C8D—C9D	109.9 (2)
C8B—C7B—H7J	108.9	N1D—C8D—C7D	111.7 (2)
H7I—C7B—H7J	107.7	C9D—C8D—C7D	109.7 (2)
N1B—C8B—C9B	112.2 (2)	N1D—C8D—H8D	108.5
N1B—C8B—C7B	110.6 (2)	C9D—C8D—H8D	108.5
C9B—C8B—C7B	108.4 (2)	C7D—C8D—H8D	108.5
N1B—C8B—H8B	108.5	O1D—C9D—O2D	124.2 (3)
C9B—C8B—H8B	108.5	O1D—C9D—C8D	123.4 (3)
C7B—C8B—H8B	108.5	O2D—C9D—C8D	112.4 (3)
O1B—C9B—O2B	124.2 (3)	O3D—C10D—N1D	119.3 (3)
O1B—C9B—C8B	119.1 (3)	O3D—C10D—C11D	121.5 (2)
O2B—C9B—C8B	116.8 (3)	N1D—C10D—C11D	119.2 (2)
O3B—C10B—N1B	120.1 (3)	C10D—C11D—C12D	115.3 (2)
O3B—C10B—C11B	123.6 (3)	C10D—C11D—C16D	108.7 (2)
N1B—C10B—C11B	116.3 (3)	C12D—C11D—C16D	110.9 (2)
C10B—C11B—C16B	113.6 (3)	C10D—C11D—H11D	107.2
C10B—C11B—C12B	109.9 (2)	C12D—C11D—H11D	107.2
C16B—C11B—C12B	110.6 (2)	C16D—C11D—H11D	107.2
C10B—C11B—H11B	107.5	C11D—C12D—C13D	109.3 (2)
C16B—C11B—H11B	107.5	C11D—C12D—H12Q	109.8
C12B—C11B—H11B	107.5	C13D—C12D—H12Q	109.8
C13B—C12B—C11B	110.3 (3)	C11D—C12D—H12R	109.8
C13B—C12B—H12I	109.6	C13D—C12D—H12R	109.8
C11B—C12B—H12I	109.6	H12Q—C12D—H12R	108.3
C13B—C12B—H12J	109.6	C14D—C13D—C12D	111.3 (2)
C11B—C12B—H12J	109.6	C14D—C13D—H13Q	109.4
H12I—C12B—H12J	108.1	C12D—C13D—H13Q	109.4
C14B—C13B—C12B	112.1 (3)	C14D—C13D—H13R	109.4
C14B—C13B—H13I	109.2	C12D—C13D—H13R	109.4
C12B—C13B—H13I	109.2	H13Q—C13D—H13R	108.0
C14B—C13B—H13J	109.2	C15D—C14D—C13D	109.3 (2)
C12B—C13B—H13J	109.2	C15D—C14D—C17D	114.1 (3)
H13I—C13B—H13J	107.9	C13D—C14D—C17D	111.7 (2)
C15B—C14B—C13B	110.4 (3)	C15D—C14D—H14D	107.1
C15B—C14B—C17B	112.9 (3)	C13D—C14D—H14D	107.1
C13B—C14B—C17B	113.4 (3)	C17D—C14D—H14D	107.1
C15B—C14B—H14B	106.6	C14D—C15D—C16D	112.0 (2)
C13B—C14B—H14B	106.6	C14D—C15D—H15Q	109.2
C17B—C14B—H14B	106.6	C16D—C15D—H15Q	109.2
C14B—C15B—C16B	112.8 (3)	C14D—C15D—H15R	109.2
C14B—C15B—H15I	109.0	C16D—C15D—H15R	109.2
C16B—C15B—H15I	109.0	H15Q—C15D—H15R	107.9
C14B—C15B—H15J	109.0	C15D—C16D—C11D	110.1 (2)
C16B—C15B—H15J	109.0	C15D—C16D—H16Q	109.6
H15I—C15B—H15J	107.8	C11D—C16D—H16Q	109.6
C11B—C16B—C15B	109.6 (3)	C15D—C16D—H16R	109.6
C11B—C16B—H16I	109.7	C11D—C16D—H16R	109.6
C15B—C16B—H16I	109.7	H16Q—C16D—H16R	108.2
C11B—C16B—H16J	109.7	C19D—C17D—C18D	110.3 (3)
C15B—C16B—H16J	109.7	C19D—C17D—C14D	114.2 (3)
H16I—C16B—H16J	108.2	C18D—C17D—C14D	112.5 (3)
C19B—C17B—C18B	109.7 (3)	C19D—C17D—H17D	106.4
C19B—C17B—C14B	111.9 (3)	C18D—C17D—H17D	106.4
C18B—C17B—C14B	113.2 (3)	C14D—C17D—H17D	106.4
C19B—C17B—H17B	107.2	C17D—C18D—H18Q	109.5
C18B—C17B—H17B	107.2	C17D—C18D—H18R	109.5
C14B—C17B—H17B	107.2	H18Q—C18D—H18R	109.5
C17B—C18B—H18I	109.5	C17D—C18D—H18S	109.5
C17B—C18B—H18J	109.5	H18Q—C18D—H18S	109.5
H18I—C18B—H18J	109.5	H18R—C18D—H18S	109.5
C17B—C18B—H18K	109.5	C17D—C19D—H19Q	109.5
H18I—C18B—H18K	109.5	C17D—C19D—H19R	109.5
H18J—C18B—H18K	109.5	H19Q—C19D—H19R	109.5
C17B—C19B—H19I	109.5	C17D—C19D—H19S	109.5
C17B—C19B—H19J	109.5	H19Q—C19D—H19S	109.5
H19I—C19B—H19J	109.5	H19R—C19D—H19S	109.5
C17B—C19B—H19K	109.5	HO4A—O4—HO4B	120 (4)
H19I—C19B—H19K	109.5	HO4A—O4—HO4C	101 (3)
H19J—C19B—H19K	109.5	HO4B—O4—HO4C	103 (4)
C9C—O2C—HO2C	107 (3)	HO5A—O5—HO5B	106 (4)
C10C—N1C—C8C	120.3 (3)	HO5A—O5—HO5C	115 (3)
C10C—N1C—HN1C	121.6 (19)	HO5B—O5—HO5C	112 (4)
N1A—C8A—C9A—O1A	−166.8 (3)	C17B—C14B—C15B—C16B	177.9 (3)
N1A—C8A—C9A—O2A	15.3 (4)	C10B—C11B—C16B—C15B	177.8 (2)
N1A—C10A—C11A—C14A	36.5 (6)	C12B—C11B—C16B—C15B	−58.1 (3)
C8A—N1A—C10A—O3A	7.5 (4)	C14B—C15B—C16B—C11B	56.7 (4)
N1B—C8B—C9B—O1B	−172.5 (3)	C15B—C14B—C17B—C19B	−168.9 (3)
N1B—C8B—C9B—O2B	8.8 (3)	C13B—C14B—C17B—C19B	64.6 (4)
N1B—C10B—C11B—C14B	163.5 (4)	C15B—C14B—C17B—C18B	66.4 (4)
C8B—N1B—C10B—O3B	6.6 (4)	C13B—C14B—C17B—C18B	−60.0 (4)
N1C—C8C—C9C—O1C	−0.8 (4)	C6C—C1C—C2C—C3C	−1.8 (5)
N1C—C8C—C9C—O2C	−179.9 (3)	C1C—C2C—C3C—C4C	2.4 (6)
N1C—C10C—C11C—C14C	32.0 (7)	C2C—C3C—C4C—C5C	−1.4 (6)
C8C—N1C—C10C—O3C	8.0 (4)	C3C—C4C—C5C—C6C	−0.2 (6)
N1D—C8D—C9D—O1D	6.7 (4)	C4C—C5C—C6C—C1C	0.7 (5)
N1D—C8D—C9D—O2D	−174.3 (2)	C4C—C5C—C6C—C7C	−179.9 (3)
N1D—C10D—C11D—C14D	21.8 (6)	C2C—C1C—C6C—C5C	0.2 (5)
C8D—N1D—C10D—O3D	8.9 (4)	C2C—C1C—C6C—C7C	−179.2 (3)
C6A—C1A—C2A—C3A	−0.5 (6)	C5C—C6C—C7C—C8C	5.4 (5)
C1A—C2A—C3A—C4A	0.2 (6)	C1C—C6C—C7C—C8C	−175.2 (3)
C2A—C3A—C4A—C5A	−0.4 (6)	C10C—N1C—C8C—C9C	77.7 (3)
C3A—C4A—C5A—C6A	0.9 (6)	C10C—N1C—C8C—C7C	−158.3 (3)
C4A—C5A—C6A—C1A	−1.1 (5)	C6C—C7C—C8C—N1C	62.7 (3)
C4A—C5A—C6A—C7A	179.7 (3)	C6C—C7C—C8C—C9C	−174.1 (3)
C2A—C1A—C6A—C5A	0.9 (5)	C7C—C8C—C9C—O1C	−125.5 (3)
C2A—C1A—C6A—C7A	−179.9 (3)	C7C—C8C—C9C—O2C	55.4 (3)
C5A—C6A—C7A—C8A	−104.6 (4)	C8C—N1C—C10C—C11C	−170.8 (2)
C1A—C6A—C7A—C8A	76.2 (4)	O3C—C10C—C11C—C12C	141.1 (3)
C10A—N1A—C8A—C9A	69.0 (3)	N1C—C10C—C11C—C12C	−40.1 (4)
C10A—N1A—C8A—C7A	−168.3 (2)	O3C—C10C—C11C—C16C	−93.4 (3)
C6A—C7A—C8A—N1A	78.9 (3)	N1C—C10C—C11C—C16C	85.3 (3)
C6A—C7A—C8A—C9A	−156.8 (3)	C10C—C11C—C12C—C13C	−176.5 (3)
C7A—C8A—C9A—O1A	68.8 (4)	C16C—C11C—C12C—C13C	58.2 (3)
C7A—C8A—C9A—O2A	−109.1 (3)	C11C—C12C—C13C—C14C	−57.5 (4)
C8A—N1A—C10A—C11A	−168.4 (2)	C12C—C13C—C14C—C15C	54.2 (4)
O3A—C10A—C11A—C12A	149.4 (3)	C12C—C13C—C14C—C17C	−176.7 (3)
N1A—C10A—C11A—C12A	−34.8 (4)	C13C—C14C—C15C—C16C	−52.9 (4)
O3A—C10A—C11A—C16A	−86.3 (3)	C17C—C14C—C15C—C16C	178.6 (3)
N1A—C10A—C11A—C16A	89.5 (3)	C14C—C15C—C16C—C11C	55.5 (4)
C10A—C11A—C12A—C13A	179.7 (2)	C10C—C11C—C16C—C15C	173.1 (3)
C16A—C11A—C12A—C13A	56.1 (3)	C12C—C11C—C16C—C15C	−57.7 (3)
C11A—C12A—C13A—C14A	−55.9 (3)	C13C—C14C—C17C—C19C	−60.6 (4)
C12A—C13A—C14A—C15A	55.4 (3)	C15C—C14C—C17C—C19C	66.5 (4)
C12A—C13A—C14A—C17A	−175.2 (3)	C13C—C14C—C17C—C18C	173.8 (3)
C13A—C14A—C15A—C16A	−56.2 (3)	C15C—C14C—C17C—C18C	−59.1 (4)
C17A—C14A—C15A—C16A	175.5 (2)	C6D—C1D—C2D—C3D	−0.3 (5)
C14A—C15A—C16A—C11A	58.1 (3)	C1D—C2D—C3D—C4D	0.9 (5)
C10A—C11A—C16A—C15A	174.7 (2)	C2D—C3D—C4D—C5D	−0.7 (5)
C12A—C11A—C16A—C15A	−57.5 (3)	C3D—C4D—C5D—C6D	−0.1 (5)
C15A—C14A—C17A—C19A	62.0 (4)	C4D—C5D—C6D—C1D	0.6 (4)
C13A—C14A—C17A—C19A	−65.0 (4)	C4D—C5D—C6D—C7D	−179.3 (3)
C15A—C14A—C17A—C18A	−62.4 (3)	C2D—C1D—C6D—C5D	−0.5 (4)
C13A—C14A—C17A—C18A	170.6 (3)	C2D—C1D—C6D—C7D	179.5 (3)
C6B—C1B—C2B—C3B	1.2 (5)	C5D—C6D—C7D—C8D	−109.9 (3)
C1B—C2B—C3B—C4B	−0.9 (5)	C1D—C6D—C7D—C8D	70.1 (3)
C2B—C3B—C4B—C5B	0.4 (5)	C10D—N1D—C8D—C9D	71.4 (3)
C3B—C4B—C5B—C6B	−0.1 (5)	C10D—N1D—C8D—C7D	−166.7 (2)
C2B—C1B—C6B—C5B	−1.0 (4)	C6D—C7D—C8D—N1D	69.7 (3)
C2B—C1B—C6B—C7B	177.1 (3)	C6D—C7D—C8D—C9D	−168.3 (2)
C4B—C5B—C6B—C1B	0.4 (4)	C7D—C8D—C9D—O1D	−116.4 (3)
C4B—C5B—C6B—C7B	−177.6 (3)	C7D—C8D—C9D—O2D	62.6 (3)
C1B—C6B—C7B—C8B	85.9 (3)	C8D—N1D—C10D—C11D	−169.5 (3)
C5B—C6B—C7B—C8B	−96.1 (3)	O3D—C10D—C11D—C12D	134.0 (3)
C10B—N1B—C8B—C9B	69.4 (3)	N1D—C10D—C11D—C12D	−47.6 (4)
C10B—N1B—C8B—C7B	−169.4 (2)	O3D—C10D—C11D—C16D	−100.7 (3)
C6B—C7B—C8B—N1B	68.8 (3)	N1D—C10D—C11D—C16D	77.6 (3)
C6B—C7B—C8B—C9B	−167.9 (2)	C10D—C11D—C12D—C13D	−178.0 (2)
C7B—C8B—C9B—O1B	65.1 (3)	C16D—C11D—C12D—C13D	57.8 (3)
C7B—C8B—C9B—O2B	−113.6 (3)	C11D—C12D—C13D—C14D	−59.8 (3)
C8B—N1B—C10B—C11B	−172.7 (3)	C12D—C13D—C14D—C15D	58.9 (3)
O3B—C10B—C11B—C16B	51.4 (4)	C12D—C13D—C14D—C17D	−173.9 (2)
N1B—C10B—C11B—C16B	−129.3 (3)	C13D—C14D—C15D—C16D	−56.6 (3)
O3B—C10B—C11B—C12B	−73.1 (4)	C17D—C14D—C15D—C16D	177.5 (3)
N1B—C10B—C11B—C12B	106.2 (3)	C14D—C15D—C16D—C11D	55.4 (3)
C10B—C11B—C12B—C13B	−175.5 (3)	C10D—C11D—C16D—C15D	176.5 (2)
C16B—C11B—C12B—C13B	58.3 (3)	C12D—C11D—C16D—C15D	−55.7 (3)
C11B—C12B—C13B—C14B	−56.0 (3)	C15D—C14D—C17D—C19D	55.0 (4)
C12B—C13B—C14B—C15B	53.4 (3)	C13D—C14D—C17D—C19D	−69.7 (4)
C12B—C13B—C14B—C17B	−178.8 (3)	C15D—C14D—C17D—C18D	−71.8 (4)
C13B—C14B—C15B—C16B	−54.0 (4)	C13D—C14D—C17D—C18D	163.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—HO2A···O1C	0.95 (2)	1.70 (2)	2.643 (3)	177 (5)
N1A—HN1A···Cl2	0.94 (2)	2.44 (2)	3.348 (3)	160 (3)
O2B—HO2B···O1D	0.95 (2)	1.72 (2)	2.653 (3)	168 (5)
N1B—HN1B···Cl1	0.91 (2)	2.34 (2)	3.237 (2)	173 (3)
O2C—HO2C···O1A	0.91 (2)	1.70 (2)	2.609 (3)	174 (4)
N1C—HN1C···Cl1	0.93 (2)	2.40 (2)	3.300 (3)	163 (3)
O2D—HO2D···O1B	0.94 (2)	1.64 (2)	2.569 (3)	168 (4)
N1D—HN1D···Cl2	0.92 (2)	2.37 (2)	3.262 (2)	163 (3)
O4—HO4A···O3C^i	0.96 (2)	1.58 (2)	2.530 (3)	172 (4)
O4—HO4B···O3D^i	0.96 (2)	1.51 (2)	2.454 (3)	166 (6)
O4—HO4C···Cl1	0.97 (2)	2.05 (2)	3.008 (2)	171 (4)
O5—HO5A···Cl2	0.96 (2)	2.00 (2)	2.959 (2)	172 (3)
O5—HO5C···O3A^ii	0.97 (2)	1.49 (2)	2.459 (3)	178 (4)
O5—HO5B···O3B^ii	0.96 (2)	1.57 (2)	2.506 (3)	165 (5)

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