Inter­molecular inter­actions, disorder and twinning in ciprofloxacin-2,2-difluoro­ethanol (2/3) and ciprofloxacin-water (3/14.5)

The anti­biotic ciprofloxacin [systematic name: 1-cyclo­propyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydro­quinoline-3-carboxyl­ate], has been crystallized as a 2:3 solvate with 2,2-difluoro­ethanol, 2C₁₇H₁₈FN₃O₃·3C₂H₄O₂, (I), and as a 3:14.5 hydrate, 3C₁₇H₁₈FN₃O₃·14.5H₂O, (II). The structure of (I) was determined using synchrotron X-ray diffraction data and refined as a two-component nonmerohedral twin. Both structures contain several independent mol­ecules in the asymmetric unit: (I) contains two zwitterionic ciprofloxacin mol­ecules and three difluoro­ethanol solvent mol­ecules, while (II) contains three zwitterionic ciprofloxacin mol­ecules and a mixture of ordered and disordered water mol­ecules. The inter­molecular inter­actions were analysed using fingerprint plots derived from Hirshfeld surfaces, providing a detailed description of the unique environment of each independent ciprofloxacin mol­ecule.

S1. Comment

Ciprofloxacin (Cf) belongs to the quinolone class of semisynthetic antibiotics (Turel, 2002; Mitscher, 2005). A search of the Cambridge Structural Database (Version 5.31 with updates to May 2010; Allen, 2002) reveals 68 crystal structures containing the Cf molecule. These include the structures of the anhydrous form (Fabbiani et al., 2009; Mahapatra et al., 2010), a hexahydrate (Turel et al., 1997; Fabbiani & Dittrich, 2008), hydrated sodium salts crystallized under high-pressure conditions and recoverable to ambient pressure (Fabbiani et al., 2009), a lactate sesquihydrate (Prasanna & Guru Row, 2001), a hemi-methanolate (Li et al., 2006), a hydrochloride 1.34-hydrate (Turel & Golobič, 2003), and several coordination complexes with group II or lanthanide elements.

While the crystal structures of coordination complexes of Cf often contain more than one Cf molecule in the asymmetric unit, (I) and (II) are the only examples known to date of non-coordination complexes where this is the case: two and three independent Cf molecules are found in (I) and (II), respectively (Figs. 1 and 2). Some differences in torsion angles are observed for the Cf molecules in the two structures (Table 1), indicating conformational variations in the relative orientation of the piperazinium ring and, in particular, of the cyclopropyl and carboxylate groups relative to the planar dihydroquinoline ring structure. In both (I) and (II), Cf exists as a zwitterion. Previous literature (Główka et al. 2003) has suggested that an in-plane conformation for quinolones, as observed for (I), is predominantly associated with a protonated carboxyl group, with exceptions being characterized by significant differences in C—O bond lengths compared with those normally observed in zwitterions. For (I) and (II), we are confident of our zwitterionic assignment on the basis of (i) the observed bond lengths of the carboxylate group, which, although significantly different for most of the molecules, are well below the expected value of 1.31 Å for a C—OH single bond [Reference for standard value?], and (ii) the fact that the H atoms of the NH₂⁺ groups are visible in difference Fourier maps.

The supramolecular architecture of both structures is dominated by three-dimensional hydrogen-bonding patterns, with different hydrogen-bonding capabilities satisfied by the symmetry-independent Cf molecules. Hydrogen-bond parameters are given in Tables 2 and 3. In (I), both Cf molecules form similarly bifurcated N—H···O(carboxylate) hydrogen bonds that define cross-linked chains of molecules A and B running in nearly perpendicular directions along the c and b axes, respectively. Symmetry-equivalent chains stack pairwise via face-to-face π–π interactions. Each of the three symmetry-independent 2,2-difluoroethanol molecules donates a hydrogen bond to the carboxylate O atom antiperiplanar to the carbonyl group: 2,2-difluoroethanol molecules B and C to Cf molecule B, and 2,2-difluoroethanol molecule A to Cf molecule A. These hydrogen bonds, together with weaker C—H···F and C—H···O interactions, contribute to the formation of the three-dimensional network (Fig. 3). The conformation of the hydroxyl group differs in the three independent 2,2-difluoroethanol molecules, with values for the C19—C18—O4—H4 torsion angle of 151, 98 and 160° for molecules A, B and C, respectively.

Although significant disorder is observed for the water molecules in (II), hydrogen bonds involving the Cf molecules are well defined, since the majority of water molecules interacting directly with Cf are ordered and their H-atom positions could be assigned from the experimental data. As in (I), each of the symmetry-independent Cf molecules forms infinite hydrogen-bonded N—H···O(carboxylate) chains. In (II), however, the hydrogen bonds in these chains are not bifurcated and involve N—H34 rather than N—H33. In addition, rather than being nearly orthogonal to each other, the chains all run along the a axis. Cross-linking of the chains occurs via a second set of N—H···O(carbonyl) hydrogen bonds, leading to the formation of trimers about a pseudo-3₁screw axis. This is in marked contrast with the structure of Cf hexahydrate, which forms a layered structure with no direct Cf···Cf contacts (Turel et al., 1997; Fabbiani & Dittrich, 2008 ?). The trimers in (II) are arranged in a hexameric fashion centred about the inversion centre at the unit-cell origin (Fig. 4). This arrangement creates channels approximately 4.5 Å in diameter that contain predominantly disordered water molecules (OW1–OW7 and OW15), as well as those that were modelled as ordered but exhibit the largest displacement parameters (OW12–OW14). The better defined water molecules, OW8–OW11, act as hydrogen-bond donor bridges, linking molecules within a trimer (OW8) and pairs of symmetry-related molecules (OW9–OW11), thereby connecting the trimers (Fig. 4 and Table 3). Within the hexameric arrangement, face-to-face π–π interactions link symmetry-equivalent Cf hydrogen-bonded chains in a manner similar to that found for the pairwise stacks of hydrogen-bonded chains in (I), albeit at slightly larger interplanar separations [3.4854 (8), 3.4980 (9) and 3.6165 (7) Å for pairwise stacks of molecules A, B and C, respectively, in (II); 3.2642 (14) and 3.4023 (14) Å for molecules A and B, respectively, in (I)]. As in the structure of (I), there are a number of C—H···O, C—H···F and C—H···π interactions that contribute to the stability of the structure.

Hirshfeld surfaces (Spackman & Byrom, 1997; McKinnon et al., 1998) and fingerprint plots (Spackman & McKinnon, 2002) have been shown to be useful tools for comparing and elucidating intermolecular interactions of molecules in different crystalline environments, including symmetry-independent molecules in the asymmetric unit (McKinnon et al., 2004, 2007). The analysis of fingerprint plots is restricted here to the structure of (I), since several water H atoms are missing from the structure of (II). Fingerprint plots for the two symmetry-independent Cf molecules and three symmetry-independent 2,2-difluoroethanol molecules in (I) are shown in Figs. 5 and 6, respectively. At first glance, the plots for Cf look quite similar in shape, which reflects the not-too-dissimilar packing environment around the two molecules. On closer inspection, the `thickness' and point density of some features, e.g. the long spikes denoting hydrogen bonding or the regions at high values of d_e and d_i, are distinct for each molecule. The asymmetry about the plot diagonal is typical of a structure that contains more than one molecule in the crystallographic asymmetric unit. Some interactions, e.g. H···H, O···H, H···O and C···H, labelled in Fig. 5 as 1, 2, 3 and 4, respectively, manifest themselves with characteristic features in the plots. For instance, it is immediately obvious that two distinct C···H interactions, namely π···H, are present, and on comparison with the plots shown in Fig. 6, the complementary H···π interactions are visible: Cf molecule A with solvent molecule C, and Cf molecule B with solvent molecule A, while solvent molecule B does not participate in such contacts. The diffuse set of points labelled 5 in Fig. 6 corresponds to H···H contacts involved in a cyclic interaction; the hydroxyl atoms O4 and H4 of solvent molecule A are approximately coplanar with atoms O1 and H5 of Cf molecule A, so that, in addition to the stronger O4—H4···O1 hydrogen bond, a much weaker C5—H5···O4 interaction [C5···O4 = 3.669 (5) Å] is also present.

Related literature

For related literature, see: Allen (2002); Fabbiani & Dittrich (2008); Fabbiani et al. (2009); Główka et al. (2003); Li et al. (2006); Mahapatra et al. (2010); McKinnon et al. (1998, 2004, 2007); Mitscher (2005); Prasanna & Guru Row (2001); Sheldrick (2008a, 2008b); Spackman & Byrom (1997); Spackman & McKinnon (2002); Turel (2002); Turel & Golobič (2003); Turel et al. (1997).

S2. Experimental

Ciprofloxacin (Sigma Aldrich) was used as received. Single crystals were obtained by recrystallization from 2,2-difluoroethanol for (I) or from water–NaOH at ca pH 12 for (II), by slow evaporation of saturated solutions under ambient conditions. Crystals of (II) were identified from a mixture also containing crystals of the known Cf hexahydrate. They can be easily distinguished by their characteristic thick block habit, compared with the thin plates typically displayed by the hexahydrate. While we have not studied in detail the conditions under which preferential or controlled crystallization of (II) occurs, we have also observed concomitant crystallisation of the two hydrates from water–NaOH (ca pH 12) at the lower temparature of 278 K. These crystals appear to be stable when kept suspended in solution for weeks under ambient conditions. Crystals of (II) have also been obtained by crystallization from an aqueous Ba(OH)₂ solution.

For (I), several crystals of various size were screened and all were found to be two-component twins. Smaller crystals were found to be better suited for data collection in terms of low mosaicity and good reflection profiles, e.g. absence of peak splitting, though data resolution was limited even using a synchrotron source. The non-merohedral twin law corresponds to a twofold rotation about the [011] direct-lattice direction. The fractional contribution of the major component was refined to 0.519 (2).

S3. Refinement

The program TWINABS (Sheldrick, 2008a) was used to generate a merged reflection file for (I) in the SHELXL HKLF5 format (Sheldrick, 2008b). Data statistics were as follows: 20118 data (4526 unique) for domain 1 only with mean I/σ(I) = 14.3; 20116 data (4515 unique) for domain 2 only with mean I/σ(I) = 14.5, and 7592 data (1975 unique) for both domains with mean I/σ(I) = 20.0. The quoted R_int value (0.07) comes from scaling all single and composite reflections involving domain 1. For the generation of an HKLF5 file, all observations containing domain 1 were chosen. Single reflections that also occur in composites were omitted for merging.

Given the low data-to-parameter ratio, non-H atoms of Cf in (I) were subjected to rigid-bond and similarity restraints, and bonds in the two Cf molecules were restrained to be the same with an s.u. of 0.02 Å. In the structure of (II), seven water O atoms (OW1–OW7) were modelled with split sites, with their occupancies set to either 50:50 or 60:40, one O atom (OW14) was modelled as half-occupied and the remaining six as fully occupied. The strategy for assigning site occupancies for OW1–OW7 and OW14 consisted of refining different models in which a variable number of occupancies were fixed and/or allowed to refine, so as to obtain an optimal R factor. Occupancies were fixed in the final refinement.

For both structures, H atoms belonging to Cf were positioned geometrically and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(parent). In both structures, N-bound H atoms in the Cf molecules were clearly visible in a difference Fourier map but were positioned geometrically and constrained to ride during refinement. For (I), hydroxyl H atoms were first located in a difference Fourier map and subsequently constrained to ride on their parent atom using a variable C—C—O—H torsion angle (AFIX 147 instruction in SHELXL97). For (II), H atoms for the eight ordered water molecules were clearly visible in a difference Fourier map. Their positions were refined subject to bond-distance and bond-angle restraints, with U_iso(H) = 1.5U_eq(O). The H atoms of the disordered water molecules could not be located, and they cannot easily be placed to form a consistent hydrogen-bonding pattern. These H atoms were therefore omitted from the structure.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: ORTEP-3 for Windows (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

	Fig. 1. The asymmetric unit of (I), with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity. Suffixes A, B and C denote symmetry-independent molecules.
	Fig. 2. The asymmetric unit of (II), with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity. For Cf, suffixes A, B and C denote symmetry-independent molecules. For the water molecules (OW), suffixes A and B denote disordered parts.
	Fig. 3. The crystal packing of (I), viewed along the b axis, illustrating the hydrogen-bonded arrangements of Cf molecules A (green in the electronic version of the paper) and B (blue). Symmetry-independent solvent molecules are coloured differently [red (molecule A), yellow (molecule B) and magenta (molecule C) in the electronic version of the paper]. O—H···O and N^+—H···O hydrogen bonds are shown as dashed lines.
	Fig. 4. The crystal packing of (II), viewed along the a axis, illustrating the hexameric arrangement of trimeric hydrogen-bonded columns of Cf molecules A (green in the electronic version of the paper), B (blue) and C (magenta). Hydrogen bonds are shown as dashed lines, and the pseudo-31 screw axis is highlighted in the upper part of the diagram. Fully occupied water molecules OW8–OW11, which are hydrogen-bonded to Cf molecules, are shown as balls and sticks. Disordered water molecules occupying the channel along the a axis are depicted as orange spheres. [Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) -x, 1 - y, 1 - z; (iii) x, -1 + y, z; (iv) 1 - x, -y, -z; (v) x, -1 + y, z.]
	Fig. 5. Fingerprint plots of Cf molecules A and B in (I). Close contacts are labelled as follows: 1 = H···H, 2 = H···O, 3 = O···H and 4 = C···H.
	Fig. 6. Fingerprint plots of solvent molecules A, B and C in (I). Close contacts are labelled as follows: 5 = H···H.

(I) 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydroquinoline-3- carboxylate–2,2-difluoroethanol (2/3)

Crystal data

2C17H18FN3O3·3C2H4F2O	Z = 2
Mr = 908.84	F(000) = 948
Triclinic, P1	Dx = 1.463 Mg m^−3
Hall symbol: -P 1	Synchrotron radiation, λ = 0.7000 Å
a = 10.9848 (4) Å	Cell parameters from 9991 reflections
b = 13.9800 (4) Å	θ = 2.3–24.6°
c = 13.9802 (4) Å	µ = 0.13 mm^−1
α = 105.6488 (18)°	T = 120 K
β = 90.352 (2)°	Block, yellow
γ = 93.364 (2)°	0.1 × 0.08 × 0.08 mm
V = 2063.22 (11) Å^3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	7072 independent reflections
Radiation source: fine-focus sealed tube	5962 reflections with I > 2σ(I)
Silicon monochromator	Rint = 0.08
ω scans	θmax = 24.6°, θmin = 1.5°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2008a)	h = −13→13
Tmin = 0.58, Tmax = 0.74	k = −16→16
51821 measured reflections	l = 0→16

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.202	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0922P)^2 + 1.8862P] where P = (Fo^2 + 2Fc^2)/3
7072 reflections	(Δ/σ)max < 0.001
571 parameters	Δρmax = 0.58 e Å^−3
522 restraints	Δρmin = −0.46 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. Refinement of F² against ALL reflections. From TWINABS: 23224 data (5427 unique) involve domain 1 only, mean I/σ 12.7 23236 data (5429 unique) involve domain 2 only, mean I/σ 12.9 9155 data (2475 unique) involve 2 domains, mean I/σ 17.1 The quoted R_int value (0.08) comes from scaling all single and composite reflections involving domain 1. For the generation of an HKLF5 file, all observations containing domain 1 were chosen. Data were merged in TWINABS according to point group -1; single reflections that also occur in composites were omitted.

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

	x	y	z	Uiso*/Ueq
C1A	0.9157 (4)	0.6677 (3)	0.9873 (3)	0.0288 (8)
H1A	0.9913	0.6568	0.9501	0.035*
C2A	0.8581 (5)	0.5807 (3)	1.0157 (3)	0.0420 (11)
H2A1	0.8170	0.5932	1.0787	0.050*
H2A2	0.8986	0.5188	0.9970	0.050*
C3A	0.8011 (4)	0.6155 (3)	0.9344 (3)	0.0386 (10)
H3A1	0.7260	0.6493	0.9483	0.046*
H3A2	0.8077	0.5748	0.8666	0.046*
C4A	0.8842 (3)	0.8470 (3)	1.0175 (3)	0.0235 (8)
C5A	0.9123 (3)	0.7794 (3)	1.1540 (3)	0.0266 (8)
H5A	0.9317	0.7250	1.1762	0.032*
C6A	0.8930 (3)	0.8662 (3)	1.2250 (3)	0.0249 (8)
C7A	0.9057 (3)	0.8645 (3)	1.3323 (3)	0.0255 (8)
C8A	0.8585 (3)	0.9511 (3)	1.1929 (2)	0.0219 (7)
C9A	0.8628 (3)	0.9378 (3)	1.0849 (3)	0.0241 (8)
C10A	0.8422 (3)	1.0192 (3)	1.0475 (3)	0.0237 (8)
H10A	0.8266	1.0805	1.0905	0.028*
C11A	0.8452 (3)	1.0080 (3)	0.9483 (3)	0.0248 (8)
C12A	0.8640 (3)	0.9176 (3)	0.8782 (2)	0.0222 (7)
C13A	0.9126 (3)	0.8245 (3)	0.7086 (2)	0.0243 (8)
H13A	0.8502	0.7704	0.6971	0.029*
H13B	0.9841	0.8044	0.7373	0.029*
C14A	0.9448 (3)	0.8467 (3)	0.6104 (3)	0.0240 (8)
H14A	1.0137	0.8953	0.6212	0.029*
H14B	0.9687	0.7863	0.5635	0.029*
C15A	0.7919 (3)	0.9719 (3)	0.6399 (2)	0.0245 (8)
H15A	0.7201	0.9920	0.6115	0.029*
H15B	0.8525	1.0275	0.6546	0.029*
C16A	0.7589 (3)	0.9448 (3)	0.7348 (3)	0.0246 (8)
H16A	0.7278	1.0018	0.7822	0.030*
H16B	0.6958	0.8912	0.7207	0.030*
C17A	0.8836 (3)	0.8363 (3)	0.9151 (3)	0.0243 (8)
H17A	0.8962	0.7747	0.8715	0.029*
F1A	0.8334 (2)	1.09146 (15)	0.91582 (15)	0.0284 (5)
N1A	0.9055 (3)	0.7661 (2)	1.0551 (2)	0.0251 (7)
N2A	0.8682 (3)	0.9135 (2)	0.7771 (2)	0.0239 (7)
N3A	0.8410 (3)	0.8854 (2)	0.5674 (2)	0.0228 (6)
H3A4	0.7814	0.8368	0.5481	0.027*
H3A3	0.8656	0.9037	0.5133	0.027*
O1A	0.9278 (3)	0.7830 (2)	1.3494 (2)	0.0404 (8)
O2A	0.8963 (2)	0.94404 (19)	1.39869 (17)	0.0276 (6)
O3A	0.8274 (2)	1.03187 (18)	1.24727 (17)	0.0253 (6)
C1B	0.4484 (4)	0.5514 (3)	0.8104 (3)	0.0319 (9)
H1B	0.5207	0.5962	0.8113	0.038*
C2B	0.4191 (4)	0.5314 (3)	0.9062 (3)	0.0395 (10)
H2B1	0.4733	0.5618	0.9627	0.047*
H2B2	0.3838	0.4657	0.9049	0.047*
C3B	0.3424 (4)	0.5984 (3)	0.8669 (3)	0.0384 (10)
H3B1	0.2610	0.5731	0.8415	0.046*
H3B2	0.3506	0.6692	0.8993	0.046*
C4B	0.3889 (3)	0.5089 (3)	0.6346 (3)	0.0254 (8)
C5B	0.4229 (3)	0.3788 (3)	0.7091 (3)	0.0260 (8)
H5B	0.4454	0.3602	0.7655	0.031*
C6B	0.3937 (3)	0.3040 (3)	0.6251 (3)	0.0256 (8)
C7B	0.4001 (3)	0.1985 (3)	0.6308 (3)	0.0245 (8)
C8B	0.3571 (3)	0.3298 (3)	0.5358 (3)	0.0242 (8)
C9B	0.3582 (3)	0.4370 (3)	0.5460 (3)	0.0254 (8)
C10B	0.3259 (3)	0.4710 (3)	0.4636 (3)	0.0250 (8)
H10B	0.3040	0.4254	0.4033	0.030*
C11B	0.3266 (3)	0.5694 (3)	0.4719 (3)	0.0267 (8)
C12B	0.3567 (3)	0.6433 (3)	0.5603 (3)	0.0240 (7)
C13B	0.4146 (4)	0.8152 (3)	0.6520 (3)	0.0282 (8)
H13C	0.4908	0.7916	0.6693	0.034*
H13D	0.3601	0.8207	0.7073	0.034*
C14B	0.4377 (3)	0.9162 (3)	0.6323 (3)	0.0268 (8)
H14C	0.4701	0.9638	0.6923	0.032*
H14D	0.4981	0.9115	0.5811	0.032*
C15B	0.2663 (4)	0.8780 (3)	0.5124 (3)	0.0273 (8)
H15C	0.3193	0.8700	0.4559	0.033*
H15D	0.1897	0.9011	0.4952	0.033*
C16B	0.2436 (3)	0.7792 (3)	0.5365 (3)	0.0260 (8)
H16C	0.1885	0.7868	0.5917	0.031*
H16D	0.2057	0.7305	0.4795	0.031*
C17B	0.3875 (3)	0.6100 (3)	0.6421 (3)	0.0260 (8)
H17B	0.4075	0.6561	0.7026	0.031*
F1B	0.3010 (2)	0.59818 (16)	0.38806 (15)	0.0318 (5)
N1B	0.4220 (3)	0.4767 (2)	0.7173 (2)	0.0278 (7)
N2B	0.3597 (3)	0.7443 (2)	0.5626 (2)	0.0261 (7)
N3B	0.3242 (3)	0.9521 (2)	0.5999 (2)	0.0247 (7)
H3B3	0.3418	1.0098	0.5844	0.030*
H3B4	0.2716	0.9640	0.6503	0.030*
O1B	0.4321 (3)	0.18655 (19)	0.71462 (19)	0.0313 (6)
O2B	0.3747 (2)	0.12815 (18)	0.55542 (18)	0.0277 (6)
O3B	0.3268 (2)	0.27002 (19)	0.45403 (18)	0.0280 (6)
O4A	0.1169 (3)	0.4141 (2)	0.7139 (2)	0.0451 (8)
H4A	0.1199	0.3536	0.6935	0.068*
C18A	0.0222 (5)	0.4457 (4)	0.6626 (4)	0.0489 (12)
H18A	−0.0543	0.4424	0.6961	0.059*
H18B	0.0129	0.4027	0.5954	0.059*
C19A	0.0542 (4)	0.5481 (3)	0.6604 (4)	0.0414 (11)
H19A	0.1343	0.5522	0.6306	0.050*
F2A	−0.0329 (3)	0.5799 (2)	0.6068 (2)	0.0654 (9)
F3A	0.0543 (4)	0.6118 (2)	0.7516 (3)	0.0825 (12)
O4B	0.3352 (3)	0.8446 (2)	0.2558 (2)	0.0403 (7)
H4B	0.4026	0.8337	0.2747	0.061*
C18B	0.2516 (4)	0.7633 (3)	0.2550 (3)	0.0383 (10)
H18C	0.1735	0.7881	0.2785	0.046*
H18D	0.2812	0.7273	0.3000	0.046*
C19B	0.2353 (4)	0.6951 (3)	0.1550 (3)	0.0430 (11)
H19B	0.2178	0.7332	0.1076	0.052*
F2B	0.3369 (3)	0.6442 (2)	0.1268 (2)	0.0624 (8)
F3B	0.1414 (3)	0.6267 (2)	0.1530 (2)	0.0614 (8)
O4C	0.6097 (3)	0.7792 (3)	1.0868 (2)	0.0481 (8)
H4C	0.6047	0.7833	1.1462	0.072*
C18C	0.5157 (4)	0.8319 (4)	1.0576 (3)	0.0440 (11)
H18E	0.5037	0.8923	1.1094	0.053*
H18F	0.4397	0.7911	1.0465	0.053*
C19C	0.5525 (4)	0.8567 (3)	0.9642 (3)	0.0363 (10)
H19C	0.6269	0.9009	0.9756	0.044*
F2C	0.5685 (3)	0.7732 (2)	0.89043 (19)	0.0515 (7)
F3C	0.4582 (3)	0.9011 (2)	0.9317 (2)	0.0612 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.048 (2)	0.0223 (19)	0.0177 (18)	0.0075 (16)	0.0020 (16)	0.0068 (15)
C2A	0.077 (3)	0.024 (2)	0.027 (2)	0.001 (2)	−0.002 (2)	0.0107 (18)
C3A	0.063 (3)	0.026 (2)	0.026 (2)	0.0006 (19)	−0.0047 (19)	0.0069 (17)
C4A	0.0321 (19)	0.0214 (18)	0.0194 (18)	0.0018 (14)	−0.0003 (14)	0.0100 (15)
C5A	0.038 (2)	0.028 (2)	0.0186 (18)	0.0029 (16)	−0.0004 (15)	0.0143 (16)
C6A	0.0349 (19)	0.0246 (19)	0.0164 (17)	0.0029 (15)	0.0012 (14)	0.0072 (15)
C7A	0.038 (2)	0.025 (2)	0.0145 (17)	0.0028 (16)	0.0018 (15)	0.0072 (15)
C8A	0.0328 (18)	0.0212 (19)	0.0120 (16)	0.0001 (14)	0.0015 (14)	0.0055 (14)
C9A	0.0332 (19)	0.0243 (19)	0.0169 (17)	0.0020 (15)	−0.0015 (14)	0.0093 (14)
C10A	0.0352 (19)	0.0184 (18)	0.0174 (17)	0.0026 (15)	−0.0010 (14)	0.0046 (14)
C11A	0.0348 (19)	0.0227 (19)	0.0210 (18)	0.0049 (15)	0.0008 (15)	0.0121 (15)
C12A	0.0295 (18)	0.0232 (18)	0.0162 (17)	0.0008 (14)	0.0009 (14)	0.0092 (14)
C13A	0.0358 (19)	0.0249 (19)	0.0146 (17)	0.0045 (15)	0.0012 (14)	0.0092 (15)
C14A	0.0335 (19)	0.0245 (19)	0.0170 (17)	0.0057 (15)	−0.0002 (14)	0.0099 (15)
C15A	0.040 (2)	0.0199 (18)	0.0154 (17)	0.0032 (15)	−0.0028 (15)	0.0080 (15)
C16A	0.0342 (19)	0.027 (2)	0.0150 (17)	0.0044 (15)	−0.0008 (14)	0.0093 (15)
C17A	0.0346 (19)	0.0216 (19)	0.0177 (17)	0.0017 (15)	−0.0011 (14)	0.0073 (15)
F1A	0.0510 (13)	0.0198 (11)	0.0181 (10)	0.0041 (9)	−0.0005 (9)	0.0109 (9)
N1A	0.0407 (17)	0.0211 (16)	0.0151 (15)	0.0041 (13)	0.0005 (12)	0.0072 (12)
N2A	0.0356 (16)	0.0231 (16)	0.0153 (14)	0.0063 (13)	−0.0001 (12)	0.0082 (13)
N3A	0.0382 (17)	0.0204 (16)	0.0119 (14)	0.0013 (13)	−0.0009 (12)	0.0080 (12)
O1A	0.081 (2)	0.0256 (15)	0.0194 (14)	0.0147 (14)	0.0003 (14)	0.0119 (12)
O2A	0.0469 (15)	0.0248 (14)	0.0140 (12)	0.0034 (11)	0.0014 (11)	0.0098 (11)
O3A	0.0427 (14)	0.0208 (14)	0.0140 (12)	0.0049 (11)	0.0016 (10)	0.0065 (11)
C1B	0.050 (2)	0.0227 (19)	0.0229 (19)	0.0040 (17)	−0.0087 (17)	0.0060 (16)
C2B	0.067 (3)	0.029 (2)	0.022 (2)	0.007 (2)	−0.0081 (19)	0.0064 (18)
C3B	0.058 (3)	0.033 (2)	0.025 (2)	0.0082 (19)	−0.0037 (18)	0.0078 (18)
C4B	0.0324 (19)	0.0245 (19)	0.0224 (18)	0.0033 (15)	0.0000 (15)	0.0114 (15)
C5B	0.037 (2)	0.0247 (19)	0.0198 (18)	0.0040 (15)	−0.0019 (15)	0.0110 (15)
C6B	0.0346 (19)	0.0217 (18)	0.0223 (18)	0.0040 (15)	−0.0011 (15)	0.0084 (15)
C7B	0.0319 (19)	0.0218 (19)	0.0224 (19)	0.0028 (14)	0.0023 (15)	0.0099 (16)
C8B	0.0309 (18)	0.0231 (19)	0.0212 (18)	0.0036 (15)	0.0024 (14)	0.0099 (15)
C9B	0.0324 (19)	0.0256 (19)	0.0211 (18)	0.0023 (15)	0.0004 (15)	0.0110 (15)
C10B	0.0367 (19)	0.0238 (19)	0.0147 (17)	0.0011 (15)	0.0015 (14)	0.0059 (15)
C11B	0.038 (2)	0.0271 (19)	0.0203 (18)	0.0049 (16)	0.0020 (15)	0.0143 (16)
C12B	0.0319 (18)	0.0220 (18)	0.0198 (18)	0.0061 (14)	0.0047 (14)	0.0080 (15)
C13B	0.039 (2)	0.0210 (19)	0.026 (2)	0.0050 (15)	−0.0018 (16)	0.0084 (16)
C14B	0.037 (2)	0.0183 (18)	0.0246 (19)	0.0035 (15)	0.0046 (15)	0.0041 (15)
C15B	0.045 (2)	0.0183 (18)	0.0199 (18)	0.0042 (16)	0.0024 (16)	0.0069 (15)
C16B	0.036 (2)	0.0210 (18)	0.0235 (19)	0.0038 (15)	−0.0010 (15)	0.0097 (15)
C17B	0.036 (2)	0.0194 (18)	0.0207 (18)	0.0013 (15)	−0.0011 (15)	0.0027 (15)
F1B	0.0569 (14)	0.0227 (11)	0.0194 (11)	0.0031 (10)	−0.0017 (10)	0.0119 (9)
N1B	0.0401 (18)	0.0218 (16)	0.0236 (16)	0.0029 (13)	−0.0057 (13)	0.0097 (13)
N2B	0.0340 (17)	0.0207 (16)	0.0244 (16)	0.0041 (13)	−0.0005 (13)	0.0070 (13)
N3B	0.0419 (17)	0.0183 (15)	0.0180 (15)	0.0052 (13)	0.0064 (13)	0.0110 (13)
O1B	0.0516 (17)	0.0241 (14)	0.0210 (13)	0.0048 (12)	−0.0052 (12)	0.0104 (11)
O2B	0.0454 (15)	0.0202 (14)	0.0202 (13)	0.0018 (11)	−0.0003 (11)	0.0104 (11)
O3B	0.0444 (15)	0.0205 (13)	0.0200 (13)	0.0004 (11)	−0.0037 (11)	0.0076 (11)
O4A	0.062 (2)	0.0324 (17)	0.0471 (19)	0.0062 (15)	−0.0055 (15)	0.0204 (15)
C18A	0.055 (3)	0.038 (3)	0.058 (3)	0.007 (2)	−0.012 (2)	0.020 (2)
C19A	0.046 (2)	0.038 (3)	0.047 (3)	0.012 (2)	0.001 (2)	0.020 (2)
F2A	0.082 (2)	0.0524 (18)	0.070 (2)	0.0205 (16)	−0.0186 (17)	0.0274 (16)
F3A	0.136 (3)	0.0416 (18)	0.064 (2)	0.0282 (19)	−0.030 (2)	−0.0004 (16)
O4B	0.0512 (18)	0.0315 (16)	0.0423 (18)	0.0083 (13)	−0.0043 (14)	0.0157 (14)
C18B	0.052 (2)	0.031 (2)	0.030 (2)	0.0073 (19)	0.0047 (19)	0.0051 (19)
C19B	0.054 (3)	0.040 (3)	0.036 (2)	0.004 (2)	0.000 (2)	0.011 (2)
F2B	0.0654 (19)	0.0564 (19)	0.0539 (18)	0.0114 (15)	0.0123 (14)	−0.0068 (15)
F3B	0.0675 (19)	0.0444 (17)	0.065 (2)	−0.0007 (14)	−0.0004 (15)	0.0039 (15)
O4C	0.058 (2)	0.060 (2)	0.0307 (17)	0.0122 (16)	0.0048 (15)	0.0194 (16)
C18C	0.045 (3)	0.054 (3)	0.034 (2)	0.003 (2)	0.0048 (19)	0.013 (2)
C19C	0.044 (2)	0.036 (2)	0.027 (2)	0.0015 (18)	−0.0041 (17)	0.0047 (19)
F2C	0.0802 (19)	0.0406 (16)	0.0323 (14)	−0.0010 (14)	0.0011 (13)	0.0084 (12)
F3C	0.0677 (19)	0.071 (2)	0.0512 (17)	0.0159 (16)	−0.0091 (14)	0.0253 (16)

Geometric parameters (Å, º)

C1A—N1A	1.456 (5)	C5B—N1B	1.343 (5)
C1A—C2A	1.487 (5)	C5B—C6B	1.366 (5)
C1A—C3A	1.502 (6)	C5B—H5B	0.930
C1A—H1A	0.980	C6B—C8B	1.450 (5)
C2A—C3A	1.498 (6)	C6B—C7B	1.505 (5)
C2A—H2A1	0.970	C7B—O2B	1.249 (4)
C2A—H2A2	0.970	C7B—O1B	1.278 (4)
C3A—H3A1	0.970	C8B—O3B	1.250 (4)
C3A—H3A2	0.970	C8B—C9B	1.466 (5)
C4A—C9A	1.395 (5)	C9B—C10B	1.411 (5)
C4A—C17A	1.397 (5)	C10B—C11B	1.348 (5)
C4A—N1A	1.400 (4)	C10B—H10B	0.930
C5A—N1A	1.346 (4)	C11B—F1B	1.370 (4)
C5A—C6A	1.373 (5)	C11B—C12B	1.404 (5)
C5A—H5A	0.930	C12B—C17B	1.392 (5)
C6A—C8A	1.446 (5)	C12B—N2B	1.402 (4)
C6A—C7A	1.512 (5)	C13B—N2B	1.470 (5)
C7A—O2A	1.251 (4)	C13B—C14B	1.518 (5)
C7A—O1A	1.263 (4)	C13B—H13C	0.970
C8A—O3A	1.246 (4)	C13B—H13D	0.970
C8A—C9A	1.473 (5)	C14B—N3B	1.483 (5)
C9A—C10A	1.404 (5)	C14B—H14C	0.970
C10A—C11A	1.353 (5)	C14B—H14D	0.970
C10A—H10A	0.930	C15B—N3B	1.485 (5)
C11A—F1A	1.374 (4)	C15B—C16B	1.515 (5)
C11A—C12A	1.402 (5)	C15B—H15C	0.970
C12A—C17A	1.396 (5)	C15B—H15D	0.970
C12A—N2A	1.400 (4)	C16B—N2B	1.470 (4)
C13A—N2A	1.462 (4)	C16B—H16C	0.970
C13A—C14A	1.526 (5)	C16B—H16D	0.970
C13A—H13A	0.970	C17B—H17B	0.930
C13A—H13B	0.970	N3B—H3B3	0.900
C14A—N3A	1.481 (4)	N3B—H3B4	0.900
C14A—H14A	0.970	O4A—C18A	1.417 (5)
C14A—H14B	0.970	O4A—H4A	0.820
C15A—N3A	1.484 (4)	C18A—C19A	1.463 (6)
C15A—C16A	1.515 (5)	C18A—H18A	0.970
C15A—H15A	0.970	C18A—H18B	0.970
C15A—H15B	0.970	C19A—F3A	1.344 (6)
C16A—N2A	1.475 (4)	C19A—F2A	1.376 (5)
C16A—H16A	0.970	C19A—H19A	0.980
C16A—H16B	0.970	O4B—C18B	1.416 (5)
C17A—H17A	0.930	O4B—H4B	0.820
N3A—H3A4	0.900	C18B—C19B	1.467 (6)
N3A—H3A3	0.900	C18B—H18C	0.970
C1B—N1B	1.449 (5)	C18B—H18D	0.970
C1B—C2B	1.474 (5)	C19B—F3B	1.360 (6)
C1B—C3B	1.494 (6)	C19B—F2B	1.362 (5)
C1B—H1B	0.980	C19B—H19B	0.980
C2B—C3B	1.502 (6)	O4C—C18C	1.422 (6)
C2B—H2B1	0.970	O4C—H4C	0.820
C2B—H2B2	0.970	C18C—C19C	1.491 (6)
C3B—H3B1	0.970	C18C—H18E	0.970
C3B—H3B2	0.970	C18C—H18F	0.970
C4B—C17B	1.390 (5)	C19C—F2C	1.354 (5)
C4B—C9B	1.393 (5)	C19C—F3C	1.374 (5)
C4B—N1B	1.402 (4)	C19C—H19C	0.980
N1A—C1A—C2A	118.0 (3)	C9B—C4B—N1B	118.1 (3)
N1A—C1A—C3A	117.2 (3)	N1B—C5B—C6B	125.7 (3)
C2A—C1A—C3A	60.2 (3)	N1B—C5B—H5B	117.2
N1A—C1A—H1A	116.5	C6B—C5B—H5B	117.2
C2A—C1A—H1A	116.5	C5B—C6B—C8B	118.9 (3)
C3A—C1A—H1A	116.5	C5B—C6B—C7B	117.8 (3)
C1A—C2A—C3A	60.4 (3)	C8B—C6B—C7B	123.3 (3)
C1A—C2A—H2A1	117.7	O2B—C7B—O1B	123.6 (3)
C3A—C2A—H2A1	117.7	O2B—C7B—C6B	119.7 (3)
C1A—C2A—H2A2	117.7	O1B—C7B—C6B	116.7 (3)
C3A—C2A—H2A2	117.7	O3B—C8B—C6B	126.3 (3)
H2A1—C2A—H2A2	114.9	O3B—C8B—C9B	119.2 (3)
C2A—C3A—C1A	59.4 (3)	C6B—C8B—C9B	114.5 (3)
C2A—C3A—H3A1	117.8	C4B—C9B—C10B	117.2 (3)
C1A—C3A—H3A1	117.8	C4B—C9B—C8B	123.2 (3)
C2A—C3A—H3A2	117.8	C10B—C9B—C8B	119.6 (3)
C1A—C3A—H3A2	117.8	C11B—C10B—C9B	120.3 (3)
H3A1—C3A—H3A2	115.0	C11B—C10B—H10B	119.9
C9A—C4A—C17A	121.3 (3)	C9B—C10B—H10B	119.9
C9A—C4A—N1A	118.1 (3)	C10B—C11B—F1B	117.7 (3)
C17A—C4A—N1A	120.6 (3)	C10B—C11B—C12B	123.6 (3)
N1A—C5A—C6A	125.7 (3)	F1B—C11B—C12B	118.6 (3)
N1A—C5A—H5A	117.2	C17B—C12B—N2B	123.1 (3)
C6A—C5A—H5A	117.2	C17B—C12B—C11B	116.3 (3)
C5A—C6A—C8A	118.5 (3)	N2B—C12B—C11B	120.5 (3)
C5A—C6A—C7A	116.8 (3)	N2B—C13B—C14B	109.4 (3)
C8A—C6A—C7A	124.6 (3)	N2B—C13B—H13C	109.8
O2A—C7A—O1A	123.9 (3)	C14B—C13B—H13C	109.8
O2A—C7A—C6A	118.4 (3)	N2B—C13B—H13D	109.8
O1A—C7A—C6A	117.7 (3)	C14B—C13B—H13D	109.8
O3A—C8A—C6A	126.5 (3)	H13C—C13B—H13D	108.3
O3A—C8A—C9A	118.9 (3)	N3B—C14B—C13B	111.4 (3)
C6A—C8A—C9A	114.6 (3)	N3B—C14B—H14C	109.3
C4A—C9A—C10A	118.3 (3)	C13B—C14B—H14C	109.3
C4A—C9A—C8A	122.9 (3)	N3B—C14B—H14D	109.3
C10A—C9A—C8A	118.8 (3)	C13B—C14B—H14D	109.3
C11A—C10A—C9A	119.5 (3)	H14C—C14B—H14D	108.0
C11A—C10A—H10A	120.2	N3B—C15B—C16B	109.5 (3)
C9A—C10A—H10A	120.2	N3B—C15B—H15C	109.8
C10A—C11A—F1A	117.4 (3)	C16B—C15B—H15C	109.8
C10A—C11A—C12A	123.8 (3)	N3B—C15B—H15D	109.8
F1A—C11A—C12A	118.8 (3)	C16B—C15B—H15D	109.8
C17A—C12A—N2A	123.4 (3)	H15C—C15B—H15D	108.2
C17A—C12A—C11A	116.7 (3)	N2B—C16B—C15B	109.8 (3)
N2A—C12A—C11A	119.8 (3)	N2B—C16B—H16C	109.7
N2A—C13A—C14A	109.5 (3)	C15B—C16B—H16C	109.7
N2A—C13A—H13A	109.8	N2B—C16B—H16D	109.7
C14A—C13A—H13A	109.8	C15B—C16B—H16D	109.7
N2A—C13A—H13B	109.8	H16C—C16B—H16D	108.2
C14A—C13A—H13B	109.8	C4B—C17B—C12B	120.9 (3)
H13A—C13A—H13B	108.2	C4B—C17B—H17B	119.6
N3A—C14A—C13A	111.9 (3)	C12B—C17B—H17B	119.6
N3A—C14A—H14A	109.2	C5B—N1B—C4B	119.6 (3)
C13A—C14A—H14A	109.2	C5B—N1B—C1B	122.3 (3)
N3A—C14A—H14B	109.2	C4B—N1B—C1B	118.0 (3)
C13A—C14A—H14B	109.2	C12B—N2B—C13B	116.6 (3)
H14A—C14A—H14B	107.9	C12B—N2B—C16B	115.1 (3)
N3A—C15A—C16A	110.1 (3)	C13B—N2B—C16B	110.1 (3)
N3A—C15A—H15A	109.6	C14B—N3B—C15B	111.2 (3)
C16A—C15A—H15A	109.6	C14B—N3B—H3B3	109.4
N3A—C15A—H15B	109.6	C15B—N3B—H3B3	109.4
C16A—C15A—H15B	109.6	C14B—N3B—H3B4	109.4
H15A—C15A—H15B	108.2	C15B—N3B—H3B4	109.4
N2A—C16A—C15A	109.4 (3)	H3B3—N3B—H3B4	108.0
N2A—C16A—H16A	109.8	C18A—O4A—H4A	109.5
C15A—C16A—H16A	109.8	O4A—C18A—C19A	108.3 (4)
N2A—C16A—H16B	109.8	O4A—C18A—H18A	110.0
C15A—C16A—H16B	109.8	C19A—C18A—H18A	110.0
H16A—C16A—H16B	108.2	O4A—C18A—H18B	110.0
C12A—C17A—C4A	120.3 (3)	C19A—C18A—H18B	110.0
C12A—C17A—H17A	119.9	H18A—C18A—H18B	108.4
C4A—C17A—H17A	119.9	F3A—C19A—F2A	104.9 (4)
C5A—N1A—C4A	119.6 (3)	F3A—C19A—C18A	111.7 (4)
C5A—N1A—C1A	120.4 (3)	F2A—C19A—C18A	110.0 (4)
C4A—N1A—C1A	120.0 (3)	F3A—C19A—H19A	110.0
C12A—N2A—C13A	118.2 (3)	F2A—C19A—H19A	110.0
C12A—N2A—C16A	115.8 (3)	C18A—C19A—H19A	110.0
C13A—N2A—C16A	110.5 (3)	C18B—O4B—H4B	109.5
C14A—N3A—C15A	111.6 (3)	O4B—C18B—C19B	111.5 (4)
C14A—N3A—H3A4	109.3	O4B—C18B—H18C	109.3
C15A—N3A—H3A4	109.3	C19B—C18B—H18C	109.3
C14A—N3A—H3A3	109.3	O4B—C18B—H18D	109.3
C15A—N3A—H3A3	109.3	C19B—C18B—H18D	109.3
H3A4—N3A—H3A3	108.0	H18C—C18B—H18D	108.0
N1B—C1B—C2B	121.1 (3)	F3B—C19B—F2B	107.3 (4)
N1B—C1B—C3B	117.2 (4)	F3B—C19B—C18B	110.3 (4)
C2B—C1B—C3B	60.8 (3)	F2B—C19B—C18B	111.2 (4)
N1B—C1B—H1B	115.5	F3B—C19B—H19B	109.4
C2B—C1B—H1B	115.5	F2B—C19B—H19B	109.4
C3B—C1B—H1B	115.5	C18B—C19B—H19B	109.4
C1B—C2B—C3B	60.3 (3)	C18C—O4C—H4C	109.5
C1B—C2B—H2B1	117.7	O4C—C18C—C19C	108.2 (4)
C3B—C2B—H2B1	117.7	O4C—C18C—H18E	110.1
C1B—C2B—H2B2	117.7	C19C—C18C—H18E	110.1
C3B—C2B—H2B2	117.7	O4C—C18C—H18F	110.1
H2B1—C2B—H2B2	114.9	C19C—C18C—H18F	110.1
C1B—C3B—C2B	58.9 (3)	H18E—C18C—H18F	108.4
C1B—C3B—H3B1	117.9	F2C—C19C—F3C	105.3 (3)
C2B—C3B—H3B1	117.9	F2C—C19C—C18C	111.1 (4)
C1B—C3B—H3B2	117.9	F3C—C19C—C18C	108.5 (4)
C2B—C3B—H3B2	117.9	F2C—C19C—H19C	110.6
H3B1—C3B—H3B2	115.0	F3C—C19C—H19C	110.6
C17B—C4B—C9B	121.7 (3)	C18C—C19C—H19C	110.6
C17B—C4B—N1B	120.2 (3)
N1A—C1A—C2A—C3A	107.0 (4)	N1B—C5B—C6B—C7B	−179.9 (4)
N1A—C1A—C3A—C2A	−108.3 (4)	C5B—C6B—C7B—O2B	−179.6 (3)
N1A—C5A—C6A—C8A	2.1 (6)	C8B—C6B—C7B—O2B	1.0 (6)
N1A—C5A—C6A—C7A	−179.9 (4)	C5B—C6B—C7B—O1B	0.3 (5)
C5A—C6A—C7A—O2A	175.6 (4)	C8B—C6B—C7B—O1B	−179.0 (3)
C8A—C6A—C7A—O2A	−6.5 (6)	C5B—C6B—C8B—O3B	−179.3 (4)
C5A—C6A—C7A—O1A	−3.0 (5)	C7B—C6B—C8B—O3B	0.0 (6)
C8A—C6A—C7A—O1A	174.9 (4)	C5B—C6B—C8B—C9B	1.2 (5)
C5A—C6A—C8A—O3A	173.2 (4)	C7B—C6B—C8B—C9B	−179.4 (3)
C7A—C6A—C8A—O3A	−4.7 (6)	C17B—C4B—C9B—C10B	0.3 (5)
C5A—C6A—C8A—C9A	−7.3 (5)	N1B—C4B—C9B—C10B	−179.7 (3)
C7A—C6A—C8A—C9A	174.8 (3)	C17B—C4B—C9B—C8B	−179.1 (3)
C17A—C4A—C9A—C10A	−1.0 (5)	N1B—C4B—C9B—C8B	0.9 (5)
N1A—C4A—C9A—C10A	179.6 (3)	O3B—C8B—C9B—C4B	179.1 (3)
C17A—C4A—C9A—C8A	177.8 (3)	C6B—C8B—C9B—C4B	−1.4 (5)
N1A—C4A—C9A—C8A	−1.6 (5)	O3B—C8B—C9B—C10B	−0.4 (5)
O3A—C8A—C9A—C4A	−173.2 (3)	C6B—C8B—C9B—C10B	179.1 (3)
C6A—C8A—C9A—C4A	7.2 (5)	C4B—C9B—C10B—C11B	0.6 (5)
O3A—C8A—C9A—C10A	5.5 (5)	C8B—C9B—C10B—C11B	−179.9 (3)
C6A—C8A—C9A—C10A	−174.0 (3)	C9B—C10B—C11B—F1B	176.5 (3)
C4A—C9A—C10A—C11A	−0.8 (5)	C9B—C10B—C11B—C12B	−1.0 (6)
C8A—C9A—C10A—C11A	−179.6 (3)	C10B—C11B—C12B—C17B	0.4 (6)
C9A—C10A—C11A—F1A	−175.4 (3)	F1B—C11B—C12B—C17B	−177.1 (3)
C9A—C10A—C11A—C12A	2.2 (6)	C10B—C11B—C12B—N2B	177.7 (4)
C10A—C11A—C12A—C17A	−1.6 (6)	F1B—C11B—C12B—N2B	0.3 (5)
F1A—C11A—C12A—C17A	175.9 (3)	N2B—C13B—C14B—N3B	56.2 (4)
C10A—C11A—C12A—N2A	−178.7 (4)	N3B—C15B—C16B—N2B	−59.4 (4)
F1A—C11A—C12A—N2A	−1.2 (5)	C9B—C4B—C17B—C12B	−0.9 (6)
N2A—C13A—C14A—N3A	−55.0 (4)	N1B—C4B—C17B—C12B	179.1 (3)
N3A—C15A—C16A—N2A	58.8 (4)	N2B—C12B—C17B—C4B	−176.7 (3)
N2A—C12A—C17A—C4A	176.7 (3)	C11B—C12B—C17B—C4B	0.5 (5)
C11A—C12A—C17A—C4A	−0.2 (5)	C6B—C5B—N1B—C4B	−0.1 (6)
C9A—C4A—C17A—C12A	1.5 (6)	C6B—C5B—N1B—C1B	176.9 (4)
N1A—C4A—C17A—C12A	−179.1 (3)	C17B—C4B—N1B—C5B	180.0 (3)
C6A—C5A—N1A—C4A	4.1 (6)	C9B—C4B—N1B—C5B	−0.1 (5)
C6A—C5A—N1A—C1A	−173.7 (4)	C17B—C4B—N1B—C1B	2.8 (5)
C9A—C4A—N1A—C5A	−4.2 (5)	C9B—C4B—N1B—C1B	−177.2 (3)
C17A—C4A—N1A—C5A	176.4 (3)	C2B—C1B—N1B—C5B	−30.5 (6)
C9A—C4A—N1A—C1A	173.7 (3)	C3B—C1B—N1B—C5B	−101.2 (4)
C17A—C4A—N1A—C1A	−5.8 (5)	C2B—C1B—N1B—C4B	146.5 (4)
C2A—C1A—N1A—C5A	37.9 (5)	C3B—C1B—N1B—C4B	75.8 (5)
C3A—C1A—N1A—C5A	106.8 (4)	C17B—C12B—N2B—C13B	8.7 (5)
C2A—C1A—N1A—C4A	−139.9 (4)	C11B—C12B—N2B—C13B	−168.5 (3)
C3A—C1A—N1A—C4A	−71.0 (5)	C17B—C12B—N2B—C16B	−122.4 (4)
C17A—C12A—N2A—C13A	−9.3 (5)	C11B—C12B—N2B—C16B	60.4 (4)
C11A—C12A—N2A—C13A	167.6 (3)	C14B—C13B—N2B—C12B	166.6 (3)
C17A—C12A—N2A—C16A	125.2 (4)	C14B—C13B—N2B—C16B	−59.9 (4)
C11A—C12A—N2A—C16A	−58.0 (4)	C15B—C16B—N2B—C12B	−163.5 (3)
C14A—C13A—N2A—C12A	−163.6 (3)	C15B—C16B—N2B—C13B	62.2 (4)
C14A—C13A—N2A—C16A	59.7 (4)	C13B—C14B—N3B—C15B	−54.8 (4)
C15A—C16A—N2A—C12A	159.8 (3)	C16B—C15B—N3B—C14B	55.7 (4)
C15A—C16A—N2A—C13A	−62.4 (4)	O4A—C18A—C19A—F3A	−66.8 (5)
C13A—C14A—N3A—C15A	53.0 (4)	O4A—C18A—C19A—F2A	177.1 (4)
C16A—C15A—N3A—C14A	−54.6 (4)	O4B—C18B—C19B—F3B	−170.6 (4)
N1B—C1B—C2B—C3B	−105.9 (4)	O4B—C18B—C19B—F2B	70.6 (5)
N1B—C1B—C3B—C2B	112.2 (4)	O4C—C18C—C19C—F2C	60.4 (5)
N1B—C5B—C6B—C8B	−0.5 (6)	O4C—C18C—C19C—F3C	175.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A3···O1A^i	0.90	2.58	3.176 (4)	125
N3A—H3A3···O2A^i	0.90	1.86	2.758 (4)	173
N3A—H3A4···O2B^ii	0.90	2.39	2.885 (4)	114
N3A—H3A4···O3B^ii	0.90	1.85	2.717 (4)	162
N3B—H3B3···O1B^iii	0.90	2.77	3.376 (4)	126
N3B—H3B3···O2B^iii	0.90	1.82	2.724 (4)	179
N3B—H3B4···O2A^iv	0.90	2.50	2.894 (4)	107
N3B—H3B4···O3A^iv	0.90	1.79	2.687 (4)	171
O4A—H4A···O1A^v	0.82	1.88	2.672 (4)	162
O4B—H4B···O1B^ii	0.82	1.87	2.666 (4)	165
O4C—H4C···O1B^v	0.82	1.93	2.733 (4)	168
C2A—H2A2···F3B^ii	0.97	2.51	3.207 (5)	128
C14A—H14A···O2A^vi	0.97	2.49	3.350 (5)	148
C14A—H14A···O3A^vi	0.97	2.49	3.274 (4)	138
C16A—H16A···O4B^vii	0.97	2.48	3.148 (5)	126
C1B—H1B···F2C	0.98	2.45	3.200 (5)	133
C14B—H14D···O2B^ii	0.97	2.34	3.295 (4)	170
C15B—H15D···O2A^iv	0.97	2.51	3.131 (5)	122
C18B—H18D···F1B	0.97	2.46	3.396 (5)	161

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

(II) 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydroquinoline-3- carboxylate–water (3/14.5)

Crystal data

3C17H18FN3O3·14.5H2O	Z = 2
Mr = 1255.26	F(000) = 1334
Triclinic, P1	Dx = 1.402 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 13.8760 (12) Å	Cell parameters from 6396 reflections
b = 15.8760 (13) Å	θ = 2.4–31.4°
c = 16.528 (2) Å	µ = 0.12 mm^−1
α = 115.755 (7)°	T = 100 K
β = 103.610 (7)°	Block, colourless
γ = 102.325 (5)°	0.30 × 0.25 × 0.20 mm
V = 2972.8 (5) Å^3

Data collection

Bruker APEXII CCD area-detector diffractometer	12150 independent reflections
Radiation source: fine-focus sealed tube	9655 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −17→17
Tmin = 0.40, Tmax = 0.43	k = −19→19
55842 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0595P)^2 + 1.7881P] where P = (Fo^2 + 2Fc^2)/3
12150 reflections	(Δ/σ)max < 0.001
907 parameters	Δρmax = 0.57 e Å^−3
34 restraints	Δρmin = −0.42 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. 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	Occ. (<1)
C1A	0.01030 (13)	0.05863 (13)	0.75199 (12)	0.0162 (3)
H1A	0.0186	−0.0063	0.7203	0.019*
C2A	−0.00057 (14)	0.08955 (14)	0.84785 (13)	0.0210 (4)
H2A1	−0.0004	0.0436	0.8718	0.025*
H2A2	−0.0460	0.1278	0.8642	0.025*
C3A	0.10167 (13)	0.13991 (13)	0.84351 (13)	0.0187 (4)
H3A1	0.1175	0.2083	0.8571	0.022*
H3A2	0.1631	0.1241	0.8647	0.022*
C4A	−0.00372 (13)	0.11147 (12)	0.63089 (12)	0.0149 (3)
C5A	−0.15004 (13)	0.07864 (13)	0.67699 (13)	0.0165 (3)
H5A	−0.1803	0.0561	0.7118	0.020*
C6A	−0.21164 (13)	0.10248 (13)	0.61823 (12)	0.0166 (3)
C7A	−0.32080 (13)	0.09554 (13)	0.62078 (13)	0.0185 (4)
C8A	−0.17049 (13)	0.13364 (12)	0.55932 (12)	0.0154 (3)
C9A	−0.06323 (13)	0.13288 (12)	0.56604 (12)	0.0155 (3)
C10A	−0.01854 (13)	0.14943 (13)	0.50339 (12)	0.0161 (3)
H10A	−0.0565	0.1621	0.4583	0.019*
C11A	0.08030 (13)	0.14676 (12)	0.50921 (12)	0.0155 (3)
C12A	0.14544 (13)	0.13332 (12)	0.57909 (12)	0.0146 (3)
C13A	0.30262 (13)	0.11202 (13)	0.65625 (12)	0.0164 (3)
H13A	0.2564	0.0512	0.6479	0.020*
H13B	0.3178	0.1665	0.7206	0.020*
C14A	0.40542 (13)	0.09951 (13)	0.64716 (13)	0.0174 (3)
H14A	0.4417	0.0897	0.6984	0.021*
H14B	0.3896	0.0404	0.5856	0.021*
C15A	0.42007 (13)	0.20740 (14)	0.57800 (13)	0.0187 (4)
H15A	0.4035	0.1510	0.5143	0.022*
H15B	0.4659	0.2669	0.5838	0.022*
C16A	0.31815 (13)	0.22165 (13)	0.58904 (13)	0.0170 (3)
H16A	0.3353	0.2810	0.6508	0.020*
H16B	0.2813	0.2317	0.5382	0.020*
C17A	0.10022 (13)	0.11484 (13)	0.63909 (12)	0.0157 (3)
H17A	0.1396	0.1045	0.6856	0.019*
F1A	0.11574 (8)	0.15200 (8)	0.44057 (7)	0.0193 (2)
N1A	−0.04887 (11)	0.08558 (11)	0.68779 (10)	0.0152 (3)
N2A	0.24798 (11)	0.13337 (11)	0.58360 (10)	0.0152 (3)
N3A	0.47622 (11)	0.18885 (11)	0.65348 (11)	0.0168 (3)
H3A3	0.4957	0.2429	0.7125	0.020*
H3A4	0.5354	0.1786	0.6452	0.020*
O1A	−0.36156 (10)	0.03730 (10)	0.64688 (10)	0.0256 (3)
O2A	−0.36312 (10)	0.14924 (11)	0.59960 (10)	0.0244 (3)
O3A	−0.22068 (9)	0.15653 (9)	0.50312 (9)	0.0194 (3)
C1B	0.29467 (14)	0.23071 (13)	0.30397 (12)	0.0182 (4)
H1C	0.3280	0.2588	0.2707	0.022*
C2B	0.20504 (15)	0.13171 (13)	0.24003 (13)	0.0223 (4)
H2C1	0.1845	0.1023	0.1706	0.027*
H2D2	0.1469	0.1188	0.2613	0.027*
C3B	0.31166 (15)	0.13773 (14)	0.29628 (14)	0.0247 (4)
H3C1	0.3175	0.1286	0.3513	0.030*
H3D2	0.3551	0.1120	0.2606	0.030*
C4B	0.38410 (13)	0.36527 (12)	0.47548 (12)	0.0149 (3)
C5B	0.19722 (13)	0.31214 (13)	0.39923 (13)	0.0167 (3)
H5C	0.1369	0.2728	0.3427	0.020*
C6B	0.18425 (13)	0.37441 (13)	0.48112 (13)	0.0166 (3)
C7B	0.07127 (14)	0.36530 (13)	0.47227 (13)	0.0193 (4)
C8B	0.27616 (13)	0.44012 (13)	0.57029 (12)	0.0159 (3)
C9B	0.37795 (13)	0.43309 (13)	0.56186 (12)	0.0155 (3)
C10B	0.47369 (14)	0.49694 (13)	0.64258 (12)	0.0166 (3)
H10C	0.4728	0.5432	0.7010	0.020*
C11B	0.56765 (13)	0.49026 (13)	0.63440 (12)	0.0164 (3)
C12B	0.57591 (13)	0.41920 (13)	0.55003 (12)	0.0152 (3)
C13B	0.67626 (13)	0.35036 (13)	0.45292 (12)	0.0168 (3)
H13C	0.6388	0.3652	0.4064	0.020*
H13D	0.6394	0.2809	0.4320	0.020*
C14B	0.78931 (14)	0.36560 (14)	0.45669 (13)	0.0187 (4)
H14C	0.7880	0.3197	0.3937	0.022*
H14D	0.8239	0.4334	0.4719	0.022*
C15B	0.84785 (14)	0.41153 (15)	0.62718 (13)	0.0217 (4)
H15C	0.8844	0.4817	0.6503	0.026*
H15D	0.8842	0.3954	0.6732	0.026*
C16B	0.73346 (14)	0.39399 (14)	0.62038 (13)	0.0188 (4)
H16C	0.6981	0.3248	0.6012	0.023*
H16D	0.7323	0.4368	0.6833	0.023*
C17B	0.48173 (13)	0.35762 (12)	0.46986 (12)	0.0151 (3)
H17C	0.4833	0.3109	0.4120	0.018*
F1B	0.65970 (8)	0.55830 (8)	0.71088 (7)	0.0204 (2)
N1B	0.29006 (11)	0.30310 (11)	0.39370 (10)	0.0162 (3)
N2B	0.67632 (11)	0.41602 (11)	0.54880 (10)	0.0158 (3)
N3B	0.85125 (11)	0.34822 (11)	0.53093 (11)	0.0188 (3)
H3B3	0.8242	0.2832	0.5128	0.023*
H3B4	0.9192	0.3626	0.5351	0.023*
O1B	0.00013 (10)	0.31583 (10)	0.38875 (10)	0.0269 (3)
O2B	0.05349 (10)	0.40641 (10)	0.54905 (10)	0.0247 (3)
O3B	0.27442 (10)	0.50037 (9)	0.64887 (9)	0.0203 (3)
C1C	0.10738 (14)	0.31041 (13)	0.07593 (13)	0.0183 (4)
H1E	0.0437	0.2727	0.0164	0.022*
C2C	0.16026 (14)	0.24825 (14)	0.10174 (13)	0.0214 (4)
H2E1	0.2371	0.2760	0.1335	0.026*
H2F2	0.1302	0.1762	0.0579	0.026*
C3C	0.09685 (15)	0.29607 (14)	0.15790 (14)	0.0221 (4)
H3E1	0.0287	0.2528	0.1476	0.027*
H3F2	0.1355	0.3526	0.2233	0.027*
C4C	0.12151 (13)	0.48096 (13)	0.11331 (12)	0.0166 (3)
C5C	0.27096 (13)	0.43313 (13)	0.10391 (12)	0.0170 (3)
H5E	0.2996	0.3830	0.0904	0.020*
C6C	0.33560 (13)	0.52667 (13)	0.12925 (12)	0.0174 (4)
C7C	0.45042 (14)	0.54273 (14)	0.14200 (12)	0.0187 (4)
C8C	0.29293 (14)	0.60469 (13)	0.14454 (12)	0.0178 (4)
C9C	0.18149 (14)	0.57680 (13)	0.13538 (12)	0.0179 (4)
C10C	0.13191 (14)	0.64792 (14)	0.14996 (13)	0.0208 (4)
H10E	0.1689	0.7116	0.1635	0.025*
C11C	0.02942 (15)	0.62282 (14)	0.14418 (13)	0.0218 (4)
C12C	−0.03129 (14)	0.52869 (14)	0.12660 (12)	0.0193 (4)
C13C	−0.20246 (14)	0.40775 (15)	0.08716 (14)	0.0250 (4)
H13E	−0.1788	0.3868	0.1330	0.030*
H13F	−0.1968	0.3639	0.0269	0.030*
C14C	−0.31720 (15)	0.40022 (16)	0.07001 (14)	0.0299 (5)
H14E	−0.3422	0.4161	0.0204	0.036*
H14F	−0.3612	0.3320	0.0470	0.036*
C15C	−0.25400 (16)	0.57458 (15)	0.20396 (15)	0.0254 (4)
H15E	−0.2581	0.6169	0.2656	0.031*
H15F	−0.2750	0.6002	0.1616	0.031*
C16C	−0.14139 (15)	0.57851 (14)	0.21914 (13)	0.0224 (4)
H16E	−0.0945	0.6468	0.2459	0.027*
H16F	−0.1185	0.5571	0.2647	0.027*
C17C	0.01608 (14)	0.45761 (13)	0.10949 (12)	0.0180 (4)
H17E	−0.0219	0.3939	0.0953	0.022*
F1C	−0.01800 (9)	0.69140 (8)	0.15369 (9)	0.0294 (3)
N1C	0.16929 (11)	0.40926 (11)	0.09739 (10)	0.0163 (3)
N2C	−0.13518 (12)	0.51201 (12)	0.12542 (11)	0.0210 (3)
N3C	−0.32810 (12)	0.47000 (12)	0.16036 (11)	0.0234 (3)
H3C4	−0.3954	0.4685	0.1468	0.028*
H3C3	−0.3144	0.4495	0.2033	0.028*
O1C	0.47208 (10)	0.46445 (10)	0.10160 (10)	0.0244 (3)
O2C	0.51768 (10)	0.62985 (9)	0.19216 (9)	0.0225 (3)
O3C	0.34399 (10)	0.69030 (9)	0.16331 (10)	0.0236 (3)
OW1A	0.6940 (3)	0.1254 (3)	1.0564 (2)	0.0384 (7)	0.50
OW1B	0.6126 (4)	0.0704 (3)	1.0436 (3)	0.0669 (12)	0.50
OW2A	0.3200 (2)	0.0970 (2)	0.04907 (19)	0.0393 (6)	0.60
OW2B	0.2159 (2)	−0.0042 (2)	−0.0927 (2)	0.0223 (7)	0.40
OW3A	0.5083 (2)	0.2178 (2)	0.2245 (2)	0.0319 (7)	0.50
OW3B	0.4730 (4)	0.2825 (4)	0.1750 (3)	0.0823 (16)	0.50
OW4A	0.2248 (2)	0.97205 (19)	0.74736 (18)	0.0330 (6)	0.60
OW4B	0.1614 (3)	0.8795 (3)	0.7071 (2)	0.0295 (8)	0.40
OW5A	0.6790 (2)	0.2961 (2)	0.1828 (2)	0.0257 (6)	0.50
OW5B	0.6683 (3)	0.2485 (3)	0.2086 (2)	0.0454 (8)	0.50
OW6A	0.8952 (3)	0.0356 (3)	0.0276 (2)	0.0237 (7)	0.50
OW6B	0.9370 (3)	0.0326 (3)	0.0136 (3)	0.0265 (7)	0.50
OW7A	0.3738 (3)	0.1689 (3)	0.9555 (3)	0.0413 (9)	0.60
OW7B	0.3657 (5)	0.1445 (4)	0.9120 (3)	0.0257 (12)	0.40
OW8	0.33039 (15)	0.85648 (12)	0.16362 (12)	0.0434 (4)
H81	0.347 (2)	0.8994 (17)	0.2238 (9)	0.065*
H82	0.335 (2)	0.8006 (13)	0.157 (2)	0.065*
OW9	0.45285 (10)	0.88062 (10)	0.58803 (10)	0.0245 (3)
H91	0.4050 (14)	0.8686 (18)	0.5370 (12)	0.037*
H92	0.5089 (12)	0.9297 (13)	0.6042 (16)	0.037*
OW10	0.88366 (12)	0.39539 (11)	0.29624 (10)	0.0312 (3)
H101	0.9215 (18)	0.3725 (18)	0.3245 (17)	0.047*
H102	0.887 (2)	0.4539 (11)	0.3383 (15)	0.047*
OW11	0.37127 (11)	0.31620 (10)	−0.08836 (10)	0.0278 (3)
H111	0.4046 (18)	0.3286 (18)	−0.1224 (15)	0.042*
H112	0.4023 (18)	0.3647 (14)	−0.0296 (9)	0.042*
OW12	0.62077 (15)	0.10562 (12)	0.27024 (12)	0.0409 (4)
H121	0.601 (2)	0.111 (2)	0.3170 (16)	0.061*
H122	0.623 (2)	0.1469 (18)	0.251 (2)	0.061*
OW13	0.85309 (12)	0.17866 (13)	−0.01946 (13)	0.0421 (4)
H131	0.8028 (17)	0.165 (2)	−0.0700 (14)	0.063*
H132	0.825 (2)	0.156 (2)	0.0111 (19)	0.063*
OW14	0.51312 (19)	0.07464 (14)	0.89016 (13)	0.0582 (5)
H141	0.548 (2)	0.116 (2)	0.9534 (8)	0.087*
H142	0.548 (2)	0.093 (3)	0.860 (2)	0.087*
OW15	0.93634 (19)	0.12971 (18)	0.22207 (17)	0.0181 (5)	0.50
H151	0.882 (2)	0.095 (2)	0.224 (3)	0.027*	0.50
H152	0.961 (3)	0.1890 (11)	0.265 (2)	0.027*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0143 (8)	0.0174 (8)	0.0199 (9)	0.0075 (7)	0.0071 (7)	0.0109 (7)
C2A	0.0192 (9)	0.0233 (9)	0.0202 (9)	0.0064 (7)	0.0080 (7)	0.0112 (8)
C3A	0.0149 (8)	0.0190 (9)	0.0209 (9)	0.0057 (7)	0.0043 (7)	0.0105 (7)
C4A	0.0135 (8)	0.0134 (8)	0.0176 (8)	0.0048 (6)	0.0068 (6)	0.0074 (7)
C5A	0.0121 (8)	0.0151 (8)	0.0212 (9)	0.0041 (6)	0.0073 (7)	0.0083 (7)
C6A	0.0128 (8)	0.0147 (8)	0.0202 (8)	0.0054 (6)	0.0060 (7)	0.0071 (7)
C7A	0.0129 (8)	0.0189 (9)	0.0206 (9)	0.0053 (7)	0.0057 (7)	0.0081 (7)
C8A	0.0129 (8)	0.0119 (8)	0.0174 (8)	0.0055 (6)	0.0036 (6)	0.0049 (7)
C9A	0.0119 (8)	0.0134 (8)	0.0189 (8)	0.0045 (6)	0.0045 (6)	0.0070 (7)
C10A	0.0139 (8)	0.0155 (8)	0.0175 (8)	0.0061 (7)	0.0035 (6)	0.0080 (7)
C11A	0.0168 (8)	0.0134 (8)	0.0152 (8)	0.0049 (6)	0.0070 (6)	0.0062 (7)
C12A	0.0129 (8)	0.0121 (8)	0.0170 (8)	0.0056 (6)	0.0056 (6)	0.0055 (7)
C13A	0.0129 (8)	0.0192 (8)	0.0195 (8)	0.0071 (7)	0.0066 (7)	0.0110 (7)
C14A	0.0150 (8)	0.0181 (8)	0.0216 (9)	0.0080 (7)	0.0073 (7)	0.0111 (7)
C15A	0.0145 (8)	0.0231 (9)	0.0226 (9)	0.0079 (7)	0.0084 (7)	0.0138 (8)
C16A	0.0142 (8)	0.0171 (8)	0.0223 (9)	0.0072 (7)	0.0072 (7)	0.0112 (7)
C17A	0.0138 (8)	0.0165 (8)	0.0185 (8)	0.0073 (7)	0.0057 (7)	0.0096 (7)
F1A	0.0166 (5)	0.0259 (5)	0.0185 (5)	0.0085 (4)	0.0083 (4)	0.0128 (4)
N1A	0.0134 (7)	0.0156 (7)	0.0182 (7)	0.0061 (6)	0.0061 (6)	0.0095 (6)
N2A	0.0117 (7)	0.0172 (7)	0.0191 (7)	0.0066 (6)	0.0066 (6)	0.0101 (6)
N3A	0.0127 (7)	0.0185 (7)	0.0196 (7)	0.0068 (6)	0.0071 (6)	0.0089 (6)
O1A	0.0163 (6)	0.0268 (7)	0.0387 (8)	0.0071 (5)	0.0127 (6)	0.0200 (6)
O2A	0.0184 (6)	0.0354 (8)	0.0327 (7)	0.0177 (6)	0.0144 (6)	0.0222 (6)
O3A	0.0141 (6)	0.0219 (6)	0.0241 (6)	0.0081 (5)	0.0061 (5)	0.0131 (5)
C1B	0.0177 (8)	0.0193 (9)	0.0145 (8)	0.0067 (7)	0.0048 (7)	0.0067 (7)
C2B	0.0215 (9)	0.0178 (9)	0.0198 (9)	0.0054 (7)	0.0046 (7)	0.0057 (7)
C3B	0.0272 (10)	0.0202 (9)	0.0216 (9)	0.0111 (8)	0.0052 (8)	0.0074 (8)
C4B	0.0151 (8)	0.0140 (8)	0.0170 (8)	0.0049 (6)	0.0048 (7)	0.0097 (7)
C5B	0.0146 (8)	0.0163 (8)	0.0189 (8)	0.0052 (7)	0.0039 (7)	0.0101 (7)
C6B	0.0149 (8)	0.0168 (8)	0.0213 (9)	0.0070 (7)	0.0063 (7)	0.0119 (7)
C7B	0.0172 (8)	0.0174 (9)	0.0255 (9)	0.0083 (7)	0.0076 (7)	0.0119 (8)
C8B	0.0172 (8)	0.0155 (8)	0.0194 (9)	0.0078 (7)	0.0076 (7)	0.0111 (7)
C9B	0.0157 (8)	0.0153 (8)	0.0181 (8)	0.0063 (7)	0.0063 (7)	0.0102 (7)
C10B	0.0189 (8)	0.0157 (8)	0.0165 (8)	0.0074 (7)	0.0078 (7)	0.0083 (7)
C11B	0.0149 (8)	0.0152 (8)	0.0157 (8)	0.0034 (7)	0.0019 (6)	0.0079 (7)
C12B	0.0149 (8)	0.0161 (8)	0.0179 (8)	0.0062 (7)	0.0072 (7)	0.0106 (7)
C13B	0.0157 (8)	0.0175 (8)	0.0179 (8)	0.0060 (7)	0.0073 (7)	0.0091 (7)
C14B	0.0173 (8)	0.0201 (9)	0.0229 (9)	0.0083 (7)	0.0099 (7)	0.0124 (7)
C15B	0.0174 (9)	0.0263 (10)	0.0205 (9)	0.0105 (7)	0.0060 (7)	0.0106 (8)
C16B	0.0174 (8)	0.0228 (9)	0.0194 (9)	0.0096 (7)	0.0077 (7)	0.0119 (7)
C17B	0.0161 (8)	0.0147 (8)	0.0163 (8)	0.0061 (7)	0.0070 (7)	0.0086 (7)
F1B	0.0141 (5)	0.0195 (5)	0.0175 (5)	0.0036 (4)	0.0022 (4)	0.0044 (4)
N1B	0.0146 (7)	0.0161 (7)	0.0161 (7)	0.0056 (6)	0.0049 (6)	0.0071 (6)
N2B	0.0140 (7)	0.0178 (7)	0.0173 (7)	0.0074 (6)	0.0063 (6)	0.0093 (6)
N3B	0.0148 (7)	0.0192 (7)	0.0240 (8)	0.0082 (6)	0.0086 (6)	0.0108 (6)
O1B	0.0168 (6)	0.0294 (7)	0.0252 (7)	0.0116 (6)	0.0025 (5)	0.0076 (6)
O2B	0.0159 (6)	0.0274 (7)	0.0263 (7)	0.0085 (5)	0.0098 (5)	0.0089 (6)
O3B	0.0182 (6)	0.0227 (7)	0.0185 (6)	0.0093 (5)	0.0076 (5)	0.0080 (5)
C1C	0.0165 (8)	0.0145 (8)	0.0184 (8)	0.0049 (7)	0.0038 (7)	0.0058 (7)
C2C	0.0199 (9)	0.0164 (9)	0.0243 (9)	0.0068 (7)	0.0040 (7)	0.0094 (7)
C3C	0.0211 (9)	0.0193 (9)	0.0231 (9)	0.0054 (7)	0.0067 (7)	0.0102 (8)
C4C	0.0180 (8)	0.0177 (8)	0.0139 (8)	0.0095 (7)	0.0044 (7)	0.0073 (7)
C5C	0.0162 (8)	0.0196 (9)	0.0150 (8)	0.0092 (7)	0.0047 (7)	0.0080 (7)
C6C	0.0159 (8)	0.0193 (9)	0.0156 (8)	0.0068 (7)	0.0045 (7)	0.0082 (7)
C7C	0.0185 (8)	0.0224 (9)	0.0150 (8)	0.0072 (7)	0.0066 (7)	0.0092 (7)
C8C	0.0176 (8)	0.0184 (9)	0.0141 (8)	0.0050 (7)	0.0021 (7)	0.0081 (7)
C9C	0.0184 (8)	0.0195 (9)	0.0153 (8)	0.0086 (7)	0.0043 (7)	0.0086 (7)
C10C	0.0221 (9)	0.0177 (9)	0.0208 (9)	0.0090 (7)	0.0049 (7)	0.0091 (7)
C11C	0.0259 (9)	0.0212 (9)	0.0215 (9)	0.0158 (8)	0.0079 (7)	0.0106 (8)
C12C	0.0187 (8)	0.0229 (9)	0.0144 (8)	0.0103 (7)	0.0039 (7)	0.0079 (7)
C13C	0.0166 (9)	0.0254 (10)	0.0228 (9)	0.0103 (8)	0.0034 (7)	0.0049 (8)
C14C	0.0188 (9)	0.0340 (11)	0.0238 (10)	0.0117 (8)	0.0042 (8)	0.0050 (9)
C15C	0.0303 (10)	0.0260 (10)	0.0291 (10)	0.0178 (8)	0.0169 (8)	0.0150 (8)
C16C	0.0246 (9)	0.0220 (9)	0.0202 (9)	0.0120 (8)	0.0089 (7)	0.0085 (8)
C17C	0.0172 (8)	0.0177 (8)	0.0170 (8)	0.0071 (7)	0.0047 (7)	0.0076 (7)
F1C	0.0303 (6)	0.0266 (6)	0.0427 (7)	0.0212 (5)	0.0169 (5)	0.0204 (5)
N1C	0.0149 (7)	0.0154 (7)	0.0171 (7)	0.0069 (6)	0.0046 (6)	0.0071 (6)
N2C	0.0185 (7)	0.0237 (8)	0.0193 (7)	0.0118 (6)	0.0069 (6)	0.0079 (6)
N3C	0.0197 (8)	0.0316 (9)	0.0229 (8)	0.0149 (7)	0.0077 (6)	0.0147 (7)
O1C	0.0187 (6)	0.0216 (7)	0.0273 (7)	0.0087 (5)	0.0097 (5)	0.0067 (6)
O2C	0.0169 (6)	0.0200 (7)	0.0240 (7)	0.0042 (5)	0.0065 (5)	0.0076 (6)
O3C	0.0218 (6)	0.0180 (6)	0.0282 (7)	0.0056 (5)	0.0053 (5)	0.0122 (6)
OW1A	0.050 (2)	0.0358 (18)	0.0405 (18)	0.0213 (16)	0.0268 (16)	0.0207 (15)
OW1B	0.082 (3)	0.067 (3)	0.042 (2)	0.039 (3)	0.014 (2)	0.018 (2)
OW2A	0.0341 (14)	0.0446 (16)	0.0382 (15)	0.0130 (12)	0.0123 (11)	0.0216 (13)
OW2B	0.0217 (16)	0.0223 (16)	0.0280 (17)	0.0101 (13)	0.0123 (14)	0.0146 (14)
OW3A	0.0267 (14)	0.0359 (16)	0.0224 (14)	0.0036 (12)	0.0099 (12)	0.0094 (12)
OW3B	0.085 (3)	0.068 (3)	0.054 (3)	0.050 (3)	0.007 (2)	−0.001 (2)
OW4A	0.0333 (13)	0.0323 (13)	0.0374 (14)	0.0109 (11)	0.0165 (11)	0.0197 (11)
OW4B	0.0233 (17)	0.037 (2)	0.0246 (18)	0.0037 (15)	0.0057 (14)	0.0178 (16)
OW5A	0.0289 (15)	0.0242 (14)	0.0308 (15)	0.0075 (12)	0.0152 (12)	0.0185 (13)
OW5B	0.0363 (18)	0.044 (2)	0.0357 (18)	0.0080 (16)	0.0062 (14)	0.0112 (17)
OW6A	0.0188 (17)	0.0277 (16)	0.0255 (16)	0.0103 (14)	0.0095 (13)	0.0128 (13)
OW6B	0.0272 (19)	0.0295 (16)	0.0300 (17)	0.0131 (16)	0.0167 (15)	0.0165 (14)
OW7A	0.0261 (16)	0.032 (2)	0.074 (3)	0.0125 (15)	0.020 (2)	0.032 (2)
OW7B	0.040 (2)	0.018 (2)	0.015 (2)	0.0085 (18)	0.017 (2)	0.0027 (19)
OW8	0.0617 (11)	0.0246 (8)	0.0324 (8)	0.0128 (8)	−0.0011 (8)	0.0159 (7)
OW9	0.0197 (7)	0.0246 (7)	0.0289 (7)	0.0057 (6)	0.0064 (6)	0.0158 (6)
OW10	0.0415 (9)	0.0324 (8)	0.0265 (8)	0.0219 (7)	0.0149 (7)	0.0157 (6)
OW11	0.0333 (8)	0.0222 (7)	0.0231 (7)	0.0059 (6)	0.0104 (6)	0.0097 (6)
OW12	0.0581 (11)	0.0306 (8)	0.0416 (9)	0.0172 (8)	0.0319 (8)	0.0174 (7)
OW13	0.0231 (8)	0.0475 (10)	0.0426 (10)	0.0131 (7)	0.0076 (7)	0.0144 (8)
OW14	0.0996 (17)	0.0378 (10)	0.0370 (10)	0.0229 (10)	0.0308 (11)	0.0171 (8)
OW15	0.0155 (12)	0.0135 (12)	0.0188 (12)	0.0029 (10)	0.0080 (10)	0.0032 (10)

Geometric parameters (Å, º)

C1A—N1A	1.455 (2)	C13B—H13D	0.970
C1A—C2A	1.497 (2)	C14B—N3B	1.490 (2)
C1A—C3A	1.505 (2)	C14B—H14C	0.970
C1A—H1A	0.980	C14B—H14D	0.970
C2A—C3A	1.507 (2)	C15B—N3B	1.486 (2)
C2A—H2A1	0.970	C15B—C16B	1.520 (2)
C2A—H2A2	0.970	C15B—H15C	0.970
C3A—H3A1	0.970	C15B—H15D	0.970
C3A—H3A2	0.970	C16B—N2B	1.479 (2)
C4A—N1A	1.396 (2)	C16B—H16C	0.970
C4A—C9A	1.402 (2)	C16B—H16D	0.970
C4A—C17A	1.404 (2)	C17B—H17C	0.930
C5A—N1A	1.347 (2)	N3B—H3B3	0.900
C5A—C6A	1.372 (2)	N3B—H3B4	0.900
C5A—H5A	0.930	C1C—N1C	1.457 (2)
C6A—C8A	1.442 (2)	C1C—C2C	1.491 (3)
C6A—C7A	1.507 (2)	C1C—C3C	1.502 (3)
C7A—O2A	1.253 (2)	C1C—H1E	0.980
C7A—O1A	1.265 (2)	C2C—C3C	1.506 (3)
C8A—O3A	1.256 (2)	C2C—H2E1	0.970
C8A—C9A	1.469 (2)	C2C—H2F2	0.970
C9A—C10A	1.412 (2)	C3C—H3E1	0.970
C10A—C11A	1.363 (2)	C3C—H3F2	0.970
C10A—H10A	0.930	C4C—N1C	1.396 (2)
C11A—F1A	1.3649 (19)	C4C—C9C	1.405 (3)
C11A—C12A	1.415 (2)	C4C—C17C	1.409 (2)
C12A—C17A	1.389 (2)	C5C—N1C	1.345 (2)
C12A—N2A	1.407 (2)	C5C—C6C	1.378 (2)
C13A—N2A	1.472 (2)	C5C—H5E	0.930
C13A—C14A	1.514 (2)	C6C—C8C	1.435 (3)
C13A—H13A	0.970	C6C—C7C	1.507 (2)
C13A—H13B	0.970	C7C—O2C	1.249 (2)
C14A—N3A	1.489 (2)	C7C—O1C	1.270 (2)
C14A—H14A	0.970	C8C—O3C	1.251 (2)
C14A—H14B	0.970	C8C—C9C	1.466 (2)
C15A—N3A	1.487 (2)	C9C—C10C	1.407 (3)
C15A—C16A	1.519 (2)	C10C—C11C	1.361 (3)
C15A—H15A	0.970	C10C—H10E	0.930
C15A—H15B	0.970	C11C—F1C	1.360 (2)
C16A—N2A	1.479 (2)	C11C—C12C	1.413 (3)
C16A—H16A	0.970	C12C—C17C	1.383 (3)
C16A—H16B	0.970	C12C—N2C	1.403 (2)
C17A—H17A	0.930	C13C—N2C	1.471 (2)
N3A—H3A3	0.900	C13C—C14C	1.519 (3)
N3A—H3A4	0.900	C13C—H13E	0.970
C1B—N1B	1.456 (2)	C13C—H13F	0.970
C1B—C2B	1.496 (2)	C14C—N3C	1.490 (2)
C1B—C3B	1.500 (3)	C14C—H14E	0.970
C1B—H1C	0.980	C14C—H14F	0.970
C2B—C3B	1.509 (3)	C15C—N3C	1.489 (3)
C2B—H2C1	0.970	C15C—C16C	1.506 (3)
C2B—H2D2	0.970	C15C—H15E	0.970
C3B—H3C1	0.970	C15C—H15F	0.970
C3B—H3D2	0.970	C16C—N2C	1.484 (2)
C4B—N1B	1.402 (2)	C16C—H16E	0.970
C4B—C9B	1.402 (2)	C16C—H16F	0.970
C4B—C17B	1.407 (2)	C17C—H17E	0.930
C5B—N1B	1.346 (2)	N3C—H3C4	0.900
C5B—C6B	1.367 (3)	N3C—H3C3	0.900
C5B—H5C	0.930	OW8—H81	0.862 (10)
C6B—C8B	1.449 (2)	OW8—H82	0.864 (10)
C6B—C7B	1.509 (2)	OW9—H91	0.856 (10)
C7B—O1B	1.258 (2)	OW9—H92	0.863 (10)
C7B—O2B	1.262 (2)	OW10—H101	0.861 (10)
C8B—O3B	1.244 (2)	OW10—H102	0.869 (10)
C8B—C9B	1.474 (2)	OW11—H111	0.865 (10)
C9B—C10B	1.410 (2)	OW11—H112	0.856 (10)
C10B—C11B	1.363 (2)	OW12—H121	0.858 (10)
C10B—H10C	0.930	OW12—H122	0.841 (10)
C11B—F1B	1.3641 (19)	OW13—H131	0.856 (10)
C11B—C12B	1.412 (2)	OW13—H132	0.850 (10)
C12B—C17B	1.390 (2)	OW14—H141	0.889 (10)
C12B—N2B	1.409 (2)	OW14—H142	0.868 (10)
C13B—N2B	1.470 (2)	OW15—H151	0.854 (10)
C13B—C14B	1.517 (2)	OW15—H152	0.821 (10)
C13B—H13C	0.970
N1A—C1A—C2A	118.73 (15)	N2B—C13B—H13C	109.6
N1A—C1A—C3A	118.99 (15)	C14B—C13B—H13C	109.6
C2A—C1A—C3A	60.26 (11)	N2B—C13B—H13D	109.6
N1A—C1A—H1A	115.8	C14B—C13B—H13D	109.6
C2A—C1A—H1A	115.8	H13C—C13B—H13D	108.1
C3A—C1A—H1A	115.8	N3B—C14B—C13B	111.25 (14)
C1A—C2A—C3A	60.11 (11)	N3B—C14B—H14C	109.4
C1A—C2A—H2A1	117.8	C13B—C14B—H14C	109.4
C3A—C2A—H2A1	117.8	N3B—C14B—H14D	109.4
C1A—C2A—H2A2	117.8	C13B—C14B—H14D	109.4
C3A—C2A—H2A2	117.8	H14C—C14B—H14D	108.0
H2A1—C2A—H2A2	114.9	N3B—C15B—C16B	110.43 (14)
C1A—C3A—C2A	59.63 (11)	N3B—C15B—H15C	109.6
C1A—C3A—H3A1	117.8	C16B—C15B—H15C	109.6
C2A—C3A—H3A1	117.8	N3B—C15B—H15D	109.6
C1A—C3A—H3A2	117.8	C16B—C15B—H15D	109.6
C2A—C3A—H3A2	117.8	H15C—C15B—H15D	108.1
H3A1—C3A—H3A2	114.9	N2B—C16B—C15B	110.21 (14)
N1A—C4A—C9A	119.47 (15)	N2B—C16B—H16C	109.6
N1A—C4A—C17A	119.37 (15)	C15B—C16B—H16C	109.6
C9A—C4A—C17A	121.15 (15)	N2B—C16B—H16D	109.6
N1A—C5A—C6A	124.66 (16)	C15B—C16B—H16D	109.6
N1A—C5A—H5A	117.7	H16C—C16B—H16D	108.1
C6A—C5A—H5A	117.7	C12B—C17B—C4B	120.60 (16)
C5A—C6A—C8A	120.10 (15)	C12B—C17B—H17C	119.7
C5A—C6A—C7A	116.51 (15)	C4B—C17B—H17C	119.7
C8A—C6A—C7A	123.38 (15)	C5B—N1B—C4B	119.40 (14)
O2A—C7A—O1A	124.93 (16)	C5B—N1B—C1B	121.16 (14)
O2A—C7A—C6A	118.16 (15)	C4B—N1B—C1B	119.44 (14)
O1A—C7A—C6A	116.87 (16)	C12B—N2B—C13B	114.80 (13)
O3A—C8A—C6A	124.85 (15)	C12B—N2B—C16B	114.05 (13)
O3A—C8A—C9A	120.64 (15)	C13B—N2B—C16B	110.00 (14)
C6A—C8A—C9A	114.46 (15)	C15B—N3B—C14B	110.99 (14)
C4A—C9A—C10A	117.65 (15)	C15B—N3B—H3B3	109.4
C4A—C9A—C8A	121.85 (15)	C14B—N3B—H3B3	109.4
C10A—C9A—C8A	120.43 (15)	C15B—N3B—H3B4	109.4
C11A—C10A—C9A	119.85 (16)	C14B—N3B—H3B4	109.4
C11A—C10A—H10A	120.1	H3B3—N3B—H3B4	108.0
C9A—C10A—H10A	120.1	N1C—C1C—C2C	120.98 (15)
C10A—C11A—F1A	117.96 (15)	N1C—C1C—C3C	119.02 (15)
C10A—C11A—C12A	123.61 (15)	C2C—C1C—C3C	60.45 (12)
F1A—C11A—C12A	118.34 (14)	N1C—C1C—H1E	115.2
C17A—C12A—N2A	122.20 (15)	C2C—C1C—H1E	115.2
C17A—C12A—C11A	116.19 (15)	C3C—C1C—H1E	115.2
N2A—C12A—C11A	121.52 (15)	C1C—C2C—C3C	60.15 (12)
N2A—C13A—C14A	111.29 (14)	C1C—C2C—H2E1	117.8
N2A—C13A—H13A	109.4	C3C—C2C—H2E1	117.8
C14A—C13A—H13A	109.4	C1C—C2C—H2F2	117.8
N2A—C13A—H13B	109.4	C3C—C2C—H2F2	117.8
C14A—C13A—H13B	109.4	H2E1—C2C—H2F2	114.9
H13A—C13A—H13B	108.0	C1C—C3C—C2C	59.40 (12)
N3A—C14A—C13A	111.20 (14)	C1C—C3C—H3E1	117.8
N3A—C14A—H14A	109.4	C2C—C3C—H3E1	117.8
C13A—C14A—H14A	109.4	C1C—C3C—H3F2	117.8
N3A—C14A—H14B	109.4	C2C—C3C—H3F2	117.8
C13A—C14A—H14B	109.4	H3E1—C3C—H3F2	115.0
H14A—C14A—H14B	108.0	N1C—C4C—C9C	118.64 (15)
N3A—C15A—C16A	110.34 (14)	N1C—C4C—C17C	120.17 (16)
N3A—C15A—H15A	109.6	C9C—C4C—C17C	121.17 (16)
C16A—C15A—H15A	109.6	N1C—C5C—C6C	124.62 (16)
N3A—C15A—H15B	109.6	N1C—C5C—H5E	117.7
C16A—C15A—H15B	109.6	C6C—C5C—H5E	117.7
H15A—C15A—H15B	108.1	C5C—C6C—C8C	119.74 (16)
N2A—C16A—C15A	110.85 (14)	C5C—C6C—C7C	117.49 (16)
N2A—C16A—H16A	109.5	C8C—C6C—C7C	122.76 (15)
C15A—C16A—H16A	109.5	O2C—C7C—O1C	124.40 (16)
N2A—C16A—H16B	109.5	O2C—C7C—C6C	119.19 (16)
C15A—C16A—H16B	109.5	O1C—C7C—C6C	116.39 (15)
H16A—C16A—H16B	108.1	O3C—C8C—C6C	124.30 (16)
C12A—C17A—C4A	121.23 (16)	O3C—C8C—C9C	120.89 (16)
C12A—C17A—H17A	119.4	C6C—C8C—C9C	114.81 (15)
C4A—C17A—H17A	119.4	C4C—C9C—C10C	118.05 (16)
C5A—N1A—C4A	119.16 (14)	C4C—C9C—C8C	122.34 (16)
C5A—N1A—C1A	120.73 (14)	C10C—C9C—C8C	119.61 (16)
C4A—N1A—C1A	119.92 (14)	C11C—C10C—C9C	119.53 (17)
C12A—N2A—C13A	114.72 (13)	C11C—C10C—H10E	120.2
C12A—N2A—C16A	114.86 (13)	C9C—C10C—H10E	120.2
C13A—N2A—C16A	111.41 (13)	F1C—C11C—C10C	118.11 (17)
C15A—N3A—C14A	110.07 (13)	F1C—C11C—C12C	118.16 (16)
C15A—N3A—H3A3	109.6	C10C—C11C—C12C	123.71 (17)
C14A—N3A—H3A3	109.6	C17C—C12C—N2C	124.13 (17)
C15A—N3A—H3A4	109.6	C17C—C12C—C11C	116.91 (16)
C14A—N3A—H3A4	109.6	N2C—C12C—C11C	118.95 (16)
H3A3—N3A—H3A4	108.2	N2C—C13C—C14C	109.37 (16)
N1B—C1B—C2B	118.88 (15)	N2C—C13C—H13E	109.8
N1B—C1B—C3B	118.66 (15)	C14C—C13C—H13E	109.8
C2B—C1B—C3B	60.49 (12)	N2C—C13C—H13F	109.8
N1B—C1B—H1C	115.8	C14C—C13C—H13F	109.8
C2B—C1B—H1C	115.8	H13E—C13C—H13F	108.2
C3B—C1B—H1C	115.8	N3C—C14C—C13C	111.28 (15)
C1B—C2B—C3B	59.90 (12)	N3C—C14C—H14E	109.4
C1B—C2B—H2C1	117.8	C13C—C14C—H14E	109.4
C3B—C2B—H2C1	117.8	N3C—C14C—H14F	109.4
C1B—C2B—H2D2	117.8	C13C—C14C—H14F	109.4
C3B—C2B—H2D2	117.8	H14E—C14C—H14F	108.0
H2C1—C2B—H2D2	114.9	N3C—C15C—C16C	110.83 (15)
C1B—C3B—C2B	59.61 (12)	N3C—C15C—H15E	109.5
C1B—C3B—H3C1	117.8	C16C—C15C—H15E	109.5
C2B—C3B—H3C1	117.8	N3C—C15C—H15F	109.5
C1B—C3B—H3D2	117.8	C16C—C15C—H15F	109.5
C2B—C3B—H3D2	117.8	H15E—C15C—H15F	108.1
H3C1—C3B—H3D2	114.9	N2C—C16C—C15C	109.68 (15)
N1B—C4B—C9B	118.69 (15)	N2C—C16C—H16E	109.7
N1B—C4B—C17B	119.79 (15)	C15C—C16C—H16E	109.7
C9B—C4B—C17B	121.51 (15)	N2C—C16C—H16F	109.7
N1B—C5B—C6B	125.37 (16)	C15C—C16C—H16F	109.7
N1B—C5B—H5C	117.3	H16E—C16C—H16F	108.2
C6B—C5B—H5C	117.3	C12C—C17C—C4C	120.53 (16)
C5B—C6B—C8B	119.56 (16)	C12C—C17C—H17E	119.7
C5B—C6B—C7B	116.10 (15)	C4C—C17C—H17E	119.7
C8B—C6B—C7B	124.27 (16)	C5C—N1C—C4C	119.74 (15)
O1B—C7B—O2B	123.89 (16)	C5C—N1C—C1C	121.74 (15)
O1B—C7B—C6B	117.96 (16)	C4C—N1C—C1C	118.50 (14)
O2B—C7B—C6B	118.14 (15)	C12C—N2C—C13C	116.74 (15)
O3B—C8B—C6B	125.38 (16)	C12C—N2C—C16C	114.00 (14)
O3B—C8B—C9B	120.20 (15)	C13C—N2C—C16C	109.68 (15)
C6B—C8B—C9B	114.40 (15)	C15C—N3C—C14C	111.43 (15)
C4B—C9B—C10B	117.85 (15)	C15C—N3C—H3C4	109.3
C4B—C9B—C8B	122.46 (15)	C14C—N3C—H3C4	109.3
C10B—C9B—C8B	119.69 (15)	C15C—N3C—H3C3	109.3
C11B—C10B—C9B	119.48 (16)	C14C—N3C—H3C3	109.3
C11B—C10B—H10C	120.3	H3C3—N3C—H3C3	108.0
C9B—C10B—H10C	120.3	H81—OW8—H82	110 (2)
C10B—C11B—F1B	118.33 (15)	H91—OW9—H92	109 (2)
C10B—C11B—C12B	123.95 (15)	H101—OW10—H102	110 (2)
F1B—C11B—C12B	117.68 (15)	H111—OW11—H112	108 (2)
C17B—C12B—N2B	123.35 (15)	H121—OW12—H122	124 (3)
C17B—C12B—C11B	116.47 (15)	H131—OW13—H132	107 (2)
N2B—C12B—C11B	120.13 (15)	H141—OW14—H142	109 (3)
N2B—C13B—C14B	110.37 (14)	H151—OW15—H152	114 (3)
N1A—C1A—C2A—C3A	−108.87 (17)	F1B—C11B—C12B—N2B	4.0 (2)
N1A—C1A—C3A—C2A	108.44 (17)	N2B—C13B—C14B—N3B	56.51 (18)
N1A—C5A—C6A—C8A	2.7 (3)	N3B—C15B—C16B—N2B	−57.95 (19)
N1A—C5A—C6A—C7A	−176.41 (16)	N2B—C12B—C17B—C4B	−179.26 (15)
C5A—C6A—C7A—O2A	153.83 (17)	C11B—C12B—C17B—C4B	−1.9 (2)
C8A—C6A—C7A—O2A	−25.3 (2)	N1B—C4B—C17B—C12B	179.50 (15)
C5A—C6A—C7A—O1A	−24.3 (2)	C9B—C4B—C17B—C12B	−1.4 (2)
C8A—C6A—C7A—O1A	156.57 (17)	C6B—C5B—N1B—C4B	−3.9 (3)
C5A—C6A—C8A—O3A	179.70 (16)	C6B—C5B—N1B—C1B	176.80 (16)
C7A—C6A—C8A—O3A	−1.2 (3)	C9B—C4B—N1B—C5B	2.0 (2)
C5A—C6A—C8A—C9A	2.3 (2)	C17B—C4B—N1B—C5B	−178.83 (15)
C7A—C6A—C8A—C9A	−178.65 (15)	C9B—C4B—N1B—C1B	−178.68 (15)
N1A—C4A—C9A—C10A	−174.15 (15)	C17B—C4B—N1B—C1B	0.5 (2)
C17A—C4A—C9A—C10A	5.4 (2)	C2B—C1B—N1B—C5B	−35.8 (2)
N1A—C4A—C9A—C8A	3.0 (2)	C3B—C1B—N1B—C5B	−105.94 (19)
C17A—C4A—C9A—C8A	−177.51 (15)	C2B—C1B—N1B—C4B	144.94 (16)
O3A—C8A—C9A—C4A	177.45 (16)	C3B—C1B—N1B—C4B	74.8 (2)
C6A—C8A—C9A—C4A	−5.0 (2)	C17B—C12B—N2B—C13B	6.7 (2)
O3A—C8A—C9A—C10A	−5.5 (2)	C11B—C12B—N2B—C13B	−170.61 (15)
C6A—C8A—C9A—C10A	172.03 (15)	C17B—C12B—N2B—C16B	−121.56 (18)
C4A—C9A—C10A—C11A	−1.6 (2)	C11B—C12B—N2B—C16B	61.2 (2)
C8A—C9A—C10A—C11A	−178.83 (15)	C14B—C13B—N2B—C12B	170.59 (14)
C9A—C10A—C11A—F1A	172.86 (15)	C14B—C13B—N2B—C16B	−59.17 (18)
C9A—C10A—C11A—C12A	−3.5 (3)	C15B—C16B—N2B—C12B	−169.26 (14)
C10A—C11A—C12A—C17A	4.8 (2)	C15B—C16B—N2B—C13B	60.10 (18)
F1A—C11A—C12A—C17A	−171.57 (14)	C16B—C15B—N3B—C14B	55.05 (19)
C10A—C11A—C12A—N2A	−178.52 (16)	C13B—C14B—N3B—C15B	−54.50 (19)
F1A—C11A—C12A—N2A	5.1 (2)	N1C—C1C—C2C—C3C	108.07 (18)
N2A—C13A—C14A—N3A	55.52 (18)	N1C—C1C—C3C—C2C	−111.22 (18)
N3A—C15A—C16A—N2A	−57.45 (19)	N1C—C5C—C6C—C8C	−4.1 (3)
N2A—C12A—C17A—C4A	−177.60 (15)	N1C—C5C—C6C—C7C	174.44 (15)
C11A—C12A—C17A—C4A	−0.9 (2)	C5C—C6C—C7C—O2C	−158.08 (16)
N1A—C4A—C17A—C12A	175.42 (15)	C8C—C6C—C7C—O2C	20.5 (3)
C9A—C4A—C17A—C12A	−4.1 (3)	C5C—C6C—C7C—O1C	20.4 (2)
C6A—C5A—N1A—C4A	−5.1 (3)	C8C—C6C—C7C—O1C	−161.07 (16)
C6A—C5A—N1A—C1A	179.94 (16)	C5C—C6C—C8C—O3C	−176.59 (16)
C9A—C4A—N1A—C5A	2.1 (2)	C7C—C6C—C8C—O3C	4.9 (3)
C17A—C4A—N1A—C5A	−177.44 (15)	C5C—C6C—C8C—C9C	2.7 (2)
C9A—C4A—N1A—C1A	177.12 (15)	C7C—C6C—C8C—C9C	−175.83 (15)
C17A—C4A—N1A—C1A	−2.4 (2)	N1C—C4C—C9C—C10C	179.16 (15)
C2A—C1A—N1A—C5A	−41.2 (2)	C17C—C4C—C9C—C10C	−2.4 (2)
C3A—C1A—N1A—C5A	−111.10 (18)	N1C—C4C—C9C—C8C	−1.5 (2)
C2A—C1A—N1A—C4A	143.87 (16)	C17C—C4C—C9C—C8C	176.92 (16)
C3A—C1A—N1A—C4A	73.9 (2)	O3C—C8C—C9C—C4C	179.29 (16)
C17A—C12A—N2A—C13A	0.2 (2)	C6C—C8C—C9C—C4C	0.0 (2)
C11A—C12A—N2A—C13A	−176.26 (15)	O3C—C8C—C9C—C10C	−1.4 (3)
C17A—C12A—N2A—C16A	−130.78 (17)	C6C—C8C—C9C—C10C	179.31 (16)
C11A—C12A—N2A—C16A	52.7 (2)	C4C—C9C—C10C—C11C	1.2 (3)
C14A—C13A—N2A—C12A	172.25 (14)	C8C—C9C—C10C—C11C	−178.12 (16)
C14A—C13A—N2A—C16A	−55.09 (18)	C9C—C10C—C11C—F1C	−176.68 (16)
C15A—C16A—N2A—C12A	−171.26 (14)	C9C—C10C—C11C—C12C	1.8 (3)
C15A—C16A—N2A—C13A	56.16 (18)	F1C—C11C—C12C—C17C	174.93 (15)
C16A—C15A—N3A—C14A	57.54 (18)	C10C—C11C—C12C—C17C	−3.5 (3)
C13A—C14A—N3A—C15A	−56.72 (18)	F1C—C11C—C12C—N2C	−3.7 (2)
N1B—C1B—C2B—C3B	−108.50 (18)	C10C—C11C—C12C—N2C	177.80 (17)
N1B—C1B—C3B—C2B	108.85 (18)	N2C—C13C—C14C—N3C	−57.0 (2)
N1B—C5B—C6B—C8B	2.4 (3)	N3C—C15C—C16C—N2C	57.8 (2)
N1B—C5B—C6B—C7B	−174.69 (16)	N2C—C12C—C17C—C4C	−179.16 (16)
C5B—C6B—C7B—O1B	−12.3 (2)	C11C—C12C—C17C—C4C	2.3 (3)
C8B—C6B—C7B—O1B	170.77 (16)	N1C—C4C—C17C—C12C	179.02 (16)
C5B—C6B—C7B—O2B	166.61 (16)	C9C—C4C—C17C—C12C	0.6 (3)
C8B—C6B—C7B—O2B	−10.3 (3)	C6C—C5C—N1C—C4C	2.5 (3)
C5B—C6B—C8B—O3B	179.39 (17)	C6C—C5C—N1C—C1C	−176.19 (16)
C7B—C6B—C8B—O3B	−3.8 (3)	C9C—C4C—N1C—C5C	0.3 (2)
C5B—C6B—C8B—C9B	0.9 (2)	C17C—C4C—N1C—C5C	−178.11 (15)
C7B—C6B—C8B—C9B	177.68 (15)	C9C—C4C—N1C—C1C	179.11 (15)
N1B—C4B—C9B—C10B	−178.26 (15)	C17C—C4C—N1C—C1C	0.7 (2)
C17B—C4B—C9B—C10B	2.6 (2)	C2C—C1C—N1C—C5C	26.9 (2)
N1B—C4B—C9B—C8B	1.1 (2)	C3C—C1C—N1C—C5C	98.0 (2)
C17B—C4B—C9B—C8B	−177.97 (15)	C2C—C1C—N1C—C4C	−151.79 (16)
O3B—C8B—C9B—C4B	178.87 (16)	C3C—C1C—N1C—C4C	−80.7 (2)
C6B—C8B—C9B—C4B	−2.5 (2)	C17C—C12C—N2C—C13C	−11.0 (3)
O3B—C8B—C9B—C10B	−1.7 (2)	C11C—C12C—N2C—C13C	167.59 (16)
C6B—C8B—C9B—C10B	176.85 (15)	C17C—C12C—N2C—C16C	118.60 (19)
C4B—C9B—C10B—C11B	−0.5 (2)	C11C—C12C—N2C—C16C	−62.8 (2)
C8B—C9B—C10B—C11B	−179.91 (15)	C14C—C13C—N2C—C12C	−167.24 (16)
C9B—C10B—C11B—F1B	174.64 (15)	C14C—C13C—N2C—C16C	61.17 (19)
C9B—C10B—C11B—C12B	−3.0 (3)	C15C—C16C—N2C—C12C	164.97 (16)
C10B—C11B—C12B—C17B	4.2 (3)	C15C—C16C—N2C—C13C	−62.01 (19)
F1B—C11B—C12B—C17B	−173.48 (14)	C16C—C15C—N3C—C14C	−53.8 (2)
C10B—C11B—C12B—N2B	−178.37 (16)	C13C—C14C—N3C—C15C	53.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A3···O2C^i	0.90	2.03	2.866 (2)	153
N3A—H3A3···O3C^i	0.90	2.29	2.903 (2)	125
N3A—H3A4···O2A^ii	0.90	1.80	2.684 (2)	166
N3B—H3B3···O3A^ii	0.90	1.90	2.782 (3)	168
N3B—H3B4···O2B^ii	0.90	1.76	2.660 (2)	173
N3C—H3C4···O1C^iii	0.90	1.79	2.682 (2)	170
N3C—H3C3···OW5A^iii	0.90	2.29	2.959 (4)	131
N3C—H3C3···O3B^iv	0.90	2.10	2.859 (2)	142
OW8—H81···O1A^iv	0.86 (1)	1.86 (1)	2.702 (2)	165 (3)
OW8—H82···O3C	0.86 (3)	1.83 (3)	2.683 (3)	170 (3)
OW9—H91···O2A^iv	0.86 (2)	2.07 (2)	2.836 (2)	149 (2)
OW9—H91···O3A^iv	0.86 (2)	2.38 (2)	3.021 (2)	133 (2)
OW9—H92···O1A^v	0.86 (2)	1.92 (2)	2.784 (2)	176 (2)
OW10—H101···O1B^ii	0.86 (3)	1.96 (3)	2.816 (2)	179 (3)
OW10—H102···O2B^i	0.87 (2)	1.99 (2)	2.826 (2)	158 (3)
OW10—H102···O3B^i	0.87 (2)	2.52 (3)	3.091 (2)	126 (2)
OW11—H111···O2C^vi	0.87 (3)	1.97 (3)	2.830 (2)	175 (2)
OW11—H112···O1C	0.86 (1)	1.88 (1)	2.731 (2)	176 (2)
OW15—H152···O1B^ii	0.82 (3)	1.99 (3)	2.787 (3)	163 (4)
OW12—H121···OW9^i	0.86 (3)	1.86 (3)	2.712 (2)	176 (3)
OW12—H122···OW3A	0.84 (3)	2.20 (3)	2.825 (4)	131 (3)
OW12—H122···OW5B	0.84 (3)	2.06 (3)	2.882 (5)	165 (3)
OW13—H131···OW8^vi	0.86 (2)	1.96 (2)	2.803 (3)	166 (2)
OW13—H132···OW1A^vii	0.85 (3)	2.16 (3)	2.930 (4)	150 (3)
OW13—H132···OW6A	0.85 (3)	2.41 (3)	2.827 (5)	111 (2)
OW14—H141···OW1A	0.89 (1)	2.25 (2)	2.910 (4)	131 (2)
OW14—H141···OW1B	0.89 (1)	2.03 (3)	2.623 (5)	123 (3)
OW14—H142···OW8^i	0.86 (4)	1.91 (4)	2.728 (3)	157 (3)
OW15—H151···OW4A^i	0.85 (3)	1.91 (3)	2.75 (3)	170 (4)

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