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ISSN: 2056-9890

A new solvate of afatinib, a specific inhibitor of the ErbB family of tyrosine kinases

aDepartment of Chemistry, Purdue University, 560 Oval Dr., W. Lafayette, IN 47907-2084, USA, bFaculty of Pharmaceutical Sciences, Department of Pharmacy, University of Sao Paulo, Sao Paulo, SP, Brazil, and cDepartment of Industrial and Physical Pharmacy, Purdue University, West Lafayette, Indiana, USA
*Correspondence e-mail: zeller4@purdue.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 6 February 2017; accepted 15 February 2017; online 21 February 2017)

Afatinib (systematic name: N-{4-(3-chloro-4-fluoro­anilino)-7-[(tetra­hydro­furan-3-yl)­oxy]quinazolin-6-yl}-4-(di­methyl­amino)­but-2-enamide), is a specific in­hibitor of the ErbB family of tyrosine kinases. The free base form crystallizes from aceto­nitrile as a mixed water–aceto­nitrile solvent, C24H25ClFN5O3·0.25C2H3N·2H2O. It crystallizes with two independent mol­ecules (A and B) in the asymmetric unit of the chiral space group P4212, but exhibits close to perfect pseudo-inversion symmetry, emulating P4/ncc that relates the two mol­ecules to each other. Exact inversion symmetry is however broken by swapping of oxygen and CH2 moieties of the outer tetra­hydro­furanyl substituents of the two independent mol­ecules. This can, in turn, be traced back to C—H⋯N and C—H⋯O inter­actions of the aceto­nitrile solvent mol­ecules with the tetra­hydro­furan oxygen and CH2 units. In the crystal, neighboring mol­ecules are connected via N—H⋯O hydrogen bonds between the secondary amine and the amide keto O atom. Additional hydrogen bonds are formed through the water solvent mol­ecules, which are engaged in O—H⋯O and O—H⋯N hydrogen bonds connecting to the di­methyl­amino N atom, the amide keto O atom, and one of the quinazoline N atoms of a neighboring mol­ecule, leading to an intricate three-dimensional hydrogen-bonded superstructure. There are two types of channels stretching along the direction of the c axis; one along the fourfold rotational axis, occupied by aceto­nitrile solvent mol­ecules situated on that axis, and parallel channels which are not occupied by any solvent.

1. Chemical context

Afatinib is an orally administered anti­tumor drug used for the treatment of patients with metastatic nonsmall cell lung carcinoma (Keating, 2014[Keating, G. M. (2014). Drugs, 74, 207-221.]). This drug is an irreversible specific inhibitor of ErbB family of tyrosine kinases, comprising EGFR (ErbB1), HER2 (ErbB2), and HER4 (ErbB4) (Hirsh, 2011[Hirsh, V. (2011). Future Oncol. 7, 817-825.]; Keating, 2014[Keating, G. M. (2014). Drugs, 74, 207-221.]). It is marketed as a dimaleate salt (Giotrif, Boehringer–Ingelheim Pharma GmbH, Ingelheim, Germany) and is reported to present polymorphism as a free base and in its salt forms, as well as an ethanol solvate (Gidwani et al., 2012[Gidwani, R. M., Hiremath, Ch., Yadav, M. D., Albrecht, W. & Fischer, D. (2012). Patent WO2012121764A1 (13 September 2012).]; Jiadeng, 2016[Jiadeng, T. (2016). Chin. Patent CN106188018A (07 December 2016).]). However, to the best of our knowledge no single-crystal structure has been described so far for any of the reported crystal forms. Herein, we describe an aceto­nitrile–water solvent structure of afatinib free base obtained via vapor diffusion experiments.

2. Structural commentary

Crystals of free base afatinib were obtained from an aceto­nitrile solution through vapor diffusion of hexa­nes. The compound crystallized in a tetra­gonal setting, space group P4212, as a mixed water–aceto­nitrile solvent with two mol­ecules of water and one-quarter mol­ecule of aceto­nitrile per formula unit of afatinib (Fig. 1[link]). Two crystallographically independent mol­ecules (A and B) of afatinib are present, and both exhibit disorder of its tetra­hydro­furan-3-yl­oxy units, with a disorder ratio of 0.718 (9):0.282 (9) for mol­ecule A and 0.787 (5):0.213 (5) for mol­ecule B. The type of disorder differs slightly between the two mol­ecules (see Fig. 2[link] and §5[link], Refinement).

[Scheme 1]
[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate minor disordered moieties C and D of the tetra­hydro­furan-3-yl­oxy units. C-atom labels of the disordered moieties have been omitted for clarity.
[Figure 2]
Figure 2
View of the two disordered tetra­hydro­furan-3-yl­oxy moieties, with 50% probability displacement ellipsoids. Dashed lines indicate minor disordered moieties C and D.

The two independent mol­ecules (A and B) are related by a pseudo-inversion center with close to centrosymmetric P4/ncc symmetry. After inversion, the two mol­ecules are nearly superimposable with only very minor deviations for the aromatic core, the chloro­fluoro­aniline substituent and the (di­methyl­amino)­but-2-enamide unit (see Fig. 3[link] for the mol­ecular overlay). Focusing only on the two major moieties exact inversion symmetry is broken solely by the positions of the tetra­hydro­furan (THF) O atoms, which are swapped with a CH2 group between the two mol­ecules. Associated with the different positions of O and CH2 moieties, and possibly providing an explanation for this observation, is an ordering of the aceto­nitrile solvent mol­ecules. Aceto­nitrile mol­ecules related by pseudo-inversion do not as expected point in opposite directions, but are co-parallel with each other. The CH3CN mol­ecules are located in channels surrounded by the tetra­hydro­furanyl units, and they inter­act with mol­ecules A and B in opposite ways. The methyl ends of both CH3CN mol­ecules form C—H⋯O hydrogen bonds with the O atoms of the major moieties of mol­ecule B, capping a tetra­mer of THF units on both sides. The nitro­gen ends of the aceto­nitrile units, on the other hand, act as acceptors of weak C—H⋯N hydrogen bonds (Fig. 4[link] and Table 1[link]). The methyl and nitro­gen ends of the linear mol­ecules are related by the pseudo-inversion operation. The different polarity of the two ends, one an hydrogen-bond donor, the other an hydrogen-bond acceptor, can thus be seen as an immediate cause for the swapping of oxygen and the CH2 groups, which are also hydrogen-bond donors and acceptors, so that an attractive rather than repulsive inter­action is maintained. Exact inversion symmetry is also broken by the different disorder patterns for the tetra­hydro­furan-3-yl­oxy units substituents (see §5[link], Refinement, and Fig. 2 for details). The absence of inversion symmetry is further evidenced by the value of the absolute structure parameter for racemic twinning, which refined to 0.02 (1), indicating a chiral or noncentrosymmetric space group incompatible with centrosymmetric P4/ncc symmetry.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N4A—H4A1⋯O4Bi 0.88 1.94 2.804 (5) 166
N3A—H3A⋯O2Aii 0.88 2.22 3.088 (5) 167
O4A—H4C⋯N5A 0.85 (5) 1.97 (5) 2.816 (6) 173 (4)
O4A—H4D⋯O5A 0.86 (5) 1.91 (5) 2.759 (6) 169 (5)
O5A—H5C⋯O2A 0.85 (3) 2.00 (4) 2.844 (4) 174 (5)
O5A—H5D⋯N1Bii 0.83 (5) 1.98 (5) 2.775 (6) 161 (5)
C4A—H4A⋯O2Aii 0.95 2.31 3.246 (6) 168
C16A—H16A⋯O4Bi 0.95 2.41 3.183 (6) 139
C22A—H22A⋯O3Aiii 0.99 2.40 3.353 (13) 162
C24A—H24A⋯O5Bi 0.99 2.50 3.388 (14) 150
N4B—H4B1⋯O4Aiv 0.88 1.96 2.820 (5) 167
N3B—H3B⋯O2Bv 0.88 2.26 3.123 (5) 166
O4B—H4E⋯N5B 0.87 (5) 1.95 (5) 2.811 (5) 175 (6)
O4B—H4F⋯O5B 0.86 (4) 1.91 (4) 2.756 (5) 169 (4)
O5B—H5E⋯O2B 0.85 (4) 1.98 (3) 2.828 (4) 173 (5)
O5B—H5F⋯N1Av 0.86 (4) 1.95 (4) 2.794 (5) 169 (5)
C4B—H4B⋯O2Bv 0.95 2.34 3.280 (6) 169
C16B—H16B⋯O4Aiv 0.95 2.42 3.197 (6) 139
C22B—H22D⋯O5Aiv 0.99 2.43 3.160 (8) 130
C24B—H24D⋯O3Bvi 0.99 2.57 3.455 (9) 149
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z-1]; (ii) -y+1, -x+1, -z; (iii) [y+{\script{1\over 2}}, -x+{\script{3\over 2}}, z]; (iv) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (v) -y+1, -x+1, -z-1; (vi) [y+{\script{1\over 2}}, -x+{\script{1\over 2}}, z].
[Figure 3]
Figure 3
Least-squares overlay of mol­ecule A (blue) on inverted mol­ecule B (green). O atoms of the tetra­hydro­furan-3-yl­oxy units are shown as red spheres to illustrate the absence of inversion symmetry in the title structure. The r.m.s. deviation is 0.6892 Å.
[Figure 4]
Figure 4
View of the inter­actions of the aceto­nitrile solvent mol­ecules with the tetra­hydro­furanyl units of mol­ecules A and B. The remaining sections of mol­ecules A and B have been omitted for clarity. Aceto­nitrile mol­ecules are located on a fourfold rotation axis hence and the H atoms are fourfold disordered. C—H⋯N and C—H⋯O hydrogen bonds are indicated as green dashed lines and the H⋯N and H⋯O distances (Å) are given (see Table 1[link]).

Bond lengths and angles in both mol­ecules are unexceptional and in the expected ranges. The central quinazoline cores of the mol­ecules are nearly planar, with maximum deviations of 0.073 (5) Å for atoms C5A and C5B in mol­ecules A and B, respectively. The but-2-enamide units are all-trans and also nearly planar (r.m.s. deviations are 0.046 Å for mol­ecule A and 0.042 Å for mol­ecule B, for all non-H atoms including the directly neighboring quinazoline C atom). Their mean planes are inclined to the quinazoline ring by 47.8 (2) and 47.3 (2)° in mol­ecules A and B, respectively. The chloro­fluoro­aniline rings are also twisted out of the mean plane of the quinazoline ring by 36.6 (2) and 36.9 (1)° for mol­ecules A and B, respectively.

The simulated powder pattern of the aceto­nitrile–water solvate reported here does not agree with any of the free base forms of afatinib A–D reported in the literature (Gidwani et al., 2012[Gidwani, R. M., Hiremath, Ch., Yadav, M. D., Albrecht, W. & Fischer, D. (2012). Patent WO2012121764A1 (13 September 2012).]).

3. Supra­molecular features

In the crystal of the title compound, neighboring mol­ecules are connected via N—H⋯O hydrogen bonds between the secondary amine and the amide keto O atom (see Table 1[link] for details). Mol­ecules are connected through pairwise hydrogen bonds, graph-set motif R2218, to their symmetry-related counterparts, creating twofold rotation symmetric dimers of A and B mol­ecules, respectively (Fig. 5[link]). Individual AA and BB dimers are arranged in infinite stacks along the c-axis direction through π-stacking inter­actions between the quinazoline units, and through weaker and more tilted π-stacking inter­actions between the annulated and the fluoro­chloro benzene rings (Fig. 6[link]). Individual stacking inter­actions between the quinazoline units are across the pseudo-inversion centers, forming close to centrosymmetric pairs of AB dimers, with an inter­planar angle between quinazoline units of only 1.24 (11)°. The centroid to centroid distance between the pyrimidine rings of the A and B mol­ecules is 3.442 (2) Å, the perpendicular distances between the two rings are 3.3144 (18) and 3.3113 (17) Å, with a slippage between the rings of 0.937 Å. The distance between annulated and chloro­fluoro­benzene rings is at 3.827 (3) Å substanti­ally larger, and the slippage is 1.506 Å. The stacks created along the c-axis direction are further stabilized via hydrogen bonds involving the solvent water mol­ecules. The O5 water mol­ecule hydrogen bonds to the N1 atom of the quinazoline unit, connecting every second mol­ecule in the infinite stacks, and the O4 water mol­ecule hydrogen bonds to the di­methyl­amine N atom and water mol­ecule O5, thus bridging the two ends of the di­methyl­amino­but-2-enamide units, giving the stacks additional support and stiffness (see Table 1[link] for details).

[Figure 5]
Figure 5
Hydrogen-bonded twofold rotation dimer of A mol­ecules, in two oblique views.
[Figure 6]
Figure 6
Stacks along the c-axis direction connected through hydrogen bonds (blue dashed lines) and ππ stacking inter­actions (green dashed lines). (a) Side view with distances (Å) between ring centroids (red spheres) involved in ππ stacking. (b) Top view down the c axis. Colour code: mol­ecule A blue, mol­ecule B green.

The four parallel stacks within each unit cell are inter­digitating with each other, and are also connected through another hydrogen bond facilitated by the water mol­ecule, which acts as a hydrogen-bonding acceptor for the amide N—H group. Additional weaker C—H⋯N and C—H⋯O inter­actions (Table 1[link]) also contribute to the structure and lattice stability (see Table 1[link] for details). In combination, these inter­actions lead to an intricate three-dimensional superstructure facilitated by hydrogen bonding, π-stacking and inter­digitation of mol­ecule side arms (Fig. 7[link]). In between the connected infinite stacks there remains some void space in the form of channels that stretch along the c-axis direction. Two different types of channels are found: channels along the fourfold rotational axis that are occupied by the aceto­nitrile solvent mol­ecules, with the solvent mol­ecules situated on that axis, and another set of parallel channels that stretch directly along the c-axis direction and are not occupied by any solvent.

[Figure 7]
Figure 7
Crystal packing viewed along the a axis, showing the inter­digitation of parallel stacks along the c-axis direction (see Fig. 4[link]) and the hydrogen bonds (dashed lines) connecting them, as well as aceto­nitrile occupied and empty channels at the A- and B-faces and the center of the unit cell, respectively.

4. Synthesis and crystallization

High-purity afatinib free base (>99%) was acquired from LC Labs and high-purity solvents (aceto­nitrile and hexa­nes) were procured from Sigma–Aldrich (Sigma–Aldrich, St Louis, MO, USA). Crystals suitable for single X-ray diffraction studies were obtained by vapor diffusion (Spingler et al., 2012[Spingler, B., Schnidrig, S., Todorova, T. & Wild, F. (2012). CrystEngComm, 14, 751-757.]), where afatinib free base was solubilized in aceto­nitrile and exposed to vapor of hexa­nes in a closed system.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The structure exhibits pseudo-inversion symmetry emulating the space group P4/ncc, with two independent mol­ecules, indicated by label suffixes A and B, in the asymmetric unit that are nearly related by a pseudo-inversion center. Exact inversion symmetry is not realized, as evidenced by the BASF value for racemic twinning, which refined to 0.02 (1). Exact inversion symmetry is broken by flipping of the THF ring, exchanging O and CH2 units, and by a different disorder pattern for the tetra­hydro­furanyl substituents of the two independent mol­ecules.

Table 2
Experimental details

Crystal data
Chemical formula 2C24H25ClFN5O3·0.5C2H3N·4H2O
Mr 1064.47
Crystal system, space group Tetragonal, P4212
Temperature (K) 100
a, c (Å) 26.2427 (4), 15.1639 (3)
V3) 10443.1 (4)
Z 8
Radiation type Cu Kα
μ (mm−1) 1.75
Crystal size (mm) 0.35 × 0.15 × 0.11
 
Data collection
Diffractometer Rigaku Rapid II curved image plate
Absorption correction Multi-scan (SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.])
Tmin, Tmax 0.681, 0.831
No. of measured, independent and observed [I > 2σ(I)] reflections 50059, 9958, 7679
Rint 0.056
(sin θ/λ)max−1) 0.617
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.122, 1.03
No. of reflections 9958
No. of parameters 797
No. of restraints 414
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.30, −0.40
Absolute structure Flack x determined using 2765 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter 0.02 (1)
Computer programs: HKL-3000 (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2016 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), SHELXLE (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

For the first mol­ecule, suffix A, the two disordered moieties differ mostly by the position of the tetra­hydro­furanyl O atom, which forms the flap of the THF's envelope conformation, and is bent to opposite sides for the two moieties. The ether O atom and the THF C atoms are only slightly shifted between the two disordered moieties. For mol­ecule B, the disorder is more pronounced and extends to the ether oxygen atom. The THF ring is mirror imaged between the two disordered units, swapping the positions of the O atom with that of a methyl­ene group and shifting the two units against each other.

All four THF moieties were restrained to have similar geometries (SAME commands of SHELXL2016; Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), and Uij components of the anisotropic displacement parameters were restrained to be similar for disordered atoms closer to each other than 1.7 Å (SIMU commands of SHELXL2016; Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]). The occupancy ratio refined to 0.718 (9):0.282 (9) for moieties A and C, and to 0.787 (5):0.213 (5) for moieties B and D.

The water H atoms were located in difference Fourier maps and refined with a distance restraint of O—H = 0.84 (2) Å, and C- and N-bound H atoms were placed in calculated positions and treated as riding, with C—H = 0.95–0.99 Å and N—H = 0.88 Å, and with Uiso(H) = 1.5Ueq(O,C-meth­yl) and 1.2Ueq(C,N) for other H atoms. Aceto­nitrile mol­ecules are located on fourfold axes and the H atoms are fourfold disordered by symmetry.

Supporting information


Computing details top

Data collection: HKL-3000 (Otwinowski & Minor, 1997); cell refinement: HKL-3000 (Otwinowski & Minor, 1997); data reduction: HKL-3000 (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

N-{4-(3-Chloro-4-fluoroanilino)-7-[(tetrahydrofuran-3-yl)oxy]quinazolin-6-yl}-4-(dimethylamino)but-2-enamide–acetonitrile–water (2/1/8) top
Crystal data top
2C24H25ClFN5O3·0.5C2H3N·4H2ODx = 1.354 Mg m3
Mr = 1064.47Cu Kα radiation, λ = 1.54178 Å
Tetragonal, P4212Cell parameters from 50059 reflections
a = 26.2427 (4) Åθ = 3.4–72.1°
c = 15.1639 (3) ŵ = 1.75 mm1
V = 10443.1 (4) Å3T = 100 K
Z = 8Needle, colorless
F(000) = 44720.35 × 0.15 × 0.11 mm
Data collection top
Rigaku Rapid II curved image plate
diffractometer
9958 independent reflections
Radiation source: microfocus X-ray tube7679 reflections with I > 2σ(I)
Laterally graded multilayer (Goebel) mirror monochromatorRint = 0.056
ω scansθmax = 72.1°, θmin = 3.4°
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
h = 3229
Tmin = 0.681, Tmax = 0.831k = 2632
50059 measured reflectionsl = 1718
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.043P)2 + 7.7055P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.30 e Å3
9958 reflectionsΔρmin = 0.40 e Å3
797 parametersExtinction correction: (SHELXL2016; Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
414 restraintsExtinction coefficient: 0.00033 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack x determined using 2765 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.02 (1)
Special details top

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

Refinement. The structure exhibits pseudo-inversion symmetry emulating the space group P4/ncc. Exact inversion symmetry is not realized (BASF value for racemic twinning 0.020 (10)).

Two tetrahydrofuran rings (related by pseudo-inversion) are disordered in differing ways. For one the ring is inverted at the oxygen. For the other the ring is mirror imaged swapping the position of the oxygen atom. All four moieties were restrained to have similar geometries, and Uij components of ADPs were restrained to be similar for disordered atoms closer to each other than 1.7 Angstrom. Occupancy ratios refined to 0.718 (9) to 0.282 (9) for moieties A and C, and to 0.787 (5) to 0.213 (5) for moieties B and D.

Water H atom O-H bond lengths were restrained to 0.84 (2) Angstrom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl1A0.54599 (6)0.23028 (6)0.07047 (8)0.0360 (4)
F1A0.53997 (14)0.11926 (14)0.0581 (2)0.0539 (11)
N1A0.75215 (15)0.32939 (16)0.2041 (2)0.0181 (9)
N2A0.69450 (16)0.27266 (17)0.1303 (2)0.0203 (10)
N3A0.72103 (16)0.19492 (16)0.0728 (2)0.0184 (10)
H3A0.7468180.1738200.0661700.022*
C1A0.7073 (2)0.3151 (2)0.1742 (3)0.0201 (12)
H1A0.6801620.3381000.1853630.024*
C2A0.7321 (2)0.24006 (19)0.1137 (3)0.0168 (11)
C3A0.78385 (19)0.25115 (19)0.1379 (3)0.0170 (12)
C4A0.82582 (19)0.22136 (19)0.1152 (3)0.0153 (11)
H4A0.8205720.1904780.0838290.018*
N4A0.91692 (16)0.20715 (16)0.1080 (2)0.0166 (10)
H4A10.9412740.2000660.1459750.020*
C5A0.87443 (19)0.2355 (2)0.1371 (3)0.0165 (11)
N5A1.04992 (17)0.12854 (18)0.1606 (3)0.0254 (11)
C6A0.88205 (19)0.2798 (2)0.1896 (3)0.0166 (11)
C7A0.84157 (19)0.31025 (19)0.2122 (3)0.0170 (11)
H7A0.8469410.3400770.2464390.020*
C8A0.79197 (19)0.2972 (2)0.1844 (2)0.0148 (11)
C9A0.6739 (2)0.1778 (2)0.0399 (3)0.0202 (12)
C10A0.6657 (2)0.1251 (2)0.0379 (3)0.0286 (13)
H10A0.6910930.1025910.0594680.034*
C11A0.6204 (3)0.1056 (2)0.0044 (4)0.0401 (16)
H11A0.6146080.0698870.0037180.048*
C12A0.5843 (2)0.1383 (2)0.0276 (4)0.0350 (15)
C13A0.5921 (2)0.1902 (2)0.0279 (3)0.0271 (13)
C14A0.6371 (2)0.2107 (2)0.0059 (3)0.0218 (12)
H14A0.6425060.2464710.0058890.026*
O2A0.89023 (13)0.20073 (14)0.03517 (19)0.0215 (8)
C15A0.92164 (19)0.1904 (2)0.0238 (3)0.0185 (12)
C16A0.96642 (19)0.1581 (2)0.0071 (3)0.0193 (12)
H16A0.9908250.1534650.0526990.023*
C17A0.9736 (2)0.1354 (2)0.0697 (3)0.0226 (13)
H17A0.9480540.1397890.1135450.027*
C18A1.0186 (2)0.1035 (2)0.0928 (3)0.0273 (14)
H18A1.0068740.0699480.1149420.033*
H18B1.0394070.0975530.0393440.033*
C19A1.0761 (2)0.1733 (2)0.1246 (4)0.0365 (15)
H19A1.1011010.1623730.0804900.055*
H19B1.0935840.1914390.1723490.055*
H19C1.0511440.1960230.0969800.055*
C20A1.0865 (2)0.0933 (2)0.1990 (4)0.0406 (15)
H20A1.1096380.0810260.1528970.061*
H20B1.0683790.0643770.2250730.061*
H20C1.1061980.1108430.2447650.061*
O1A0.93145 (13)0.28774 (13)0.2136 (2)0.0206 (8)
C21A0.9410 (6)0.3289 (5)0.2758 (17)0.022 (2)0.718 (9)
H21A0.9152220.3288310.3243860.027*0.718 (9)
C22A0.9429 (4)0.3805 (5)0.2302 (6)0.028 (2)0.718 (9)
H22A0.9137500.4021230.2480090.034*0.718 (9)
H22B0.9426570.3765990.1652260.034*0.718 (9)
C23A0.9922 (4)0.4027 (4)0.2612 (6)0.035 (2)0.718 (9)
H23A0.9877160.4204780.3182910.042*0.718 (9)
H23B1.0059220.4271430.2174960.042*0.718 (9)
O3A1.0252 (2)0.3599 (2)0.2706 (4)0.0374 (16)0.718 (9)
C24A0.9951 (6)0.3219 (4)0.3124 (14)0.028 (2)0.718 (9)
H24A1.0081220.2874360.2983840.034*0.718 (9)
H24B0.9953810.3264760.3772120.034*0.718 (9)
C21C0.9418 (16)0.3249 (13)0.281 (5)0.024 (3)0.282 (9)
H21C0.9191600.3184160.3325910.029*0.282 (9)
C22C0.9382 (9)0.3802 (12)0.2548 (16)0.026 (3)0.282 (9)
H22E0.9073380.3959980.2803760.031*0.282 (9)
H22F0.9368490.3837240.1898200.031*0.282 (9)
C23C0.9853 (9)0.4050 (8)0.2906 (15)0.032 (3)0.282 (9)
H23E0.9758590.4330070.3312120.039*0.282 (9)
H23F1.0057440.4194620.2418210.039*0.282 (9)
O3C1.0136 (5)0.3679 (5)0.3358 (10)0.037 (3)0.282 (9)
C24C0.9974 (16)0.3185 (9)0.309 (4)0.029 (3)0.282 (9)
H24E1.0183200.3062840.2584840.035*0.282 (9)
H24F1.0003480.2938840.3576810.035*0.282 (9)
O4A0.99752 (15)0.18082 (17)0.2950 (2)0.0274 (9)
H4C1.011 (2)0.164 (2)0.253 (3)0.041*
H4D0.9765 (17)0.2009 (18)0.269 (3)0.041*
O5A0.92301 (15)0.23351 (18)0.2047 (2)0.0360 (10)
H5C0.912 (2)0.226 (2)0.154 (2)0.054*
H5D0.8972 (16)0.246 (2)0.228 (4)0.054*
N6A0.5000000.0000000.0706 (10)0.100 (5)
C25A0.5000000.0000000.0068 (10)0.065 (5)
C26A0.5000000.0000000.1044 (10)0.096 (6)
H26A0.4709930.0186580.1254640.144*0.25
H26B0.5306620.0157920.1254640.144*0.25
H26C0.4983460.0344500.1254640.144*0.25
Cl1B0.95744 (6)0.26892 (6)0.55731 (8)0.0386 (4)
F1B0.96334 (12)0.37984 (13)0.5399 (2)0.0437 (9)
N1B0.74716 (16)0.16513 (17)0.3001 (2)0.0194 (10)
N2B0.80584 (16)0.22306 (17)0.3705 (2)0.0202 (10)
N3B0.77931 (16)0.30174 (16)0.4234 (2)0.0167 (9)
H3B0.7534080.3226210.4306700.020*
C1B0.7923 (2)0.1797 (2)0.3279 (3)0.0211 (12)
H1B0.8193310.1565530.3165120.025*
C2B0.7685 (2)0.25621 (19)0.3862 (3)0.0167 (11)
C3B0.71662 (19)0.24443 (19)0.3633 (3)0.0143 (11)
C4B0.67449 (19)0.27542 (19)0.3855 (3)0.0170 (11)
H4B0.6797620.3067500.4155100.020*
N4B0.58392 (16)0.28961 (16)0.3930 (2)0.0197 (10)
H4B10.5590660.2958930.3556430.024*
C5B0.6261 (2)0.2604 (2)0.3638 (3)0.0175 (11)
N5B0.45204 (17)0.37462 (18)0.6582 (2)0.0253 (11)
C6B0.6177 (2)0.2159 (2)0.3129 (3)0.0223 (12)
C7B0.6581 (2)0.1847 (2)0.2923 (3)0.0204 (12)
H7B0.6525260.1541740.2600970.024*
C8B0.7077 (2)0.1982 (2)0.3191 (3)0.0183 (12)
C9B0.8275 (2)0.3199 (2)0.4520 (3)0.0176 (11)
C10B0.8359 (2)0.3723 (2)0.4483 (3)0.0208 (11)
H10B0.8104180.3941570.4247510.025*
C11B0.8815 (2)0.3928 (2)0.4789 (3)0.0274 (13)
H11B0.8873330.4284970.4769020.033*
C12B0.9179 (2)0.3606 (2)0.5119 (3)0.0285 (13)
C13B0.9105 (2)0.3082 (2)0.5159 (3)0.0243 (12)
C14B0.8650 (2)0.2880 (2)0.4860 (3)0.0214 (12)
H14B0.8593250.2522580.4887620.026*
O2B0.61156 (13)0.29856 (14)0.53473 (19)0.0209 (8)
C15B0.58026 (19)0.3081 (2)0.4757 (3)0.0170 (11)
C16B0.53511 (19)0.3408 (2)0.4920 (3)0.0202 (12)
H16B0.5104400.3447960.4466290.024*
C17B0.5283 (2)0.36465 (19)0.5681 (3)0.0206 (12)
H17B0.5536180.3605440.6123260.025*
C18B0.4836 (2)0.3974 (2)0.5888 (3)0.0272 (14)
H18C0.4627810.4021460.5349750.033*
H18D0.4955620.4313800.6083480.033*
C19B0.4253 (2)0.3290 (2)0.6251 (3)0.0325 (14)
H19D0.4051290.3139790.6728420.049*
H19E0.4027410.3387440.5764900.049*
H19F0.4503460.3041350.6041110.049*
C20B0.4154 (2)0.4119 (2)0.6936 (4)0.0407 (15)
H20D0.3968540.3966620.7430900.061*
H20E0.4337460.4421960.7139000.061*
H20F0.3912520.4215130.6472040.061*
O1B0.56935 (19)0.2103 (2)0.2827 (3)0.0193 (12)0.787 (5)
C21B0.5595 (2)0.1713 (3)0.2175 (4)0.0215 (14)0.787 (5)
H21B0.5880060.1687420.1739610.026*0.787 (5)
C22B0.5094 (2)0.1847 (3)0.1725 (4)0.0226 (14)0.787 (5)
H22C0.5094180.1738410.1099820.027*0.787 (5)
H22D0.5024610.2217100.1757060.027*0.787 (5)
C23B0.4716 (3)0.1550 (3)0.2253 (5)0.0273 (15)0.787 (5)
H23C0.4401050.1489260.1909390.033*0.787 (5)
H23D0.4626780.1732370.2803210.033*0.787 (5)
O3B0.49710 (19)0.10754 (19)0.2447 (3)0.0357 (13)0.787 (5)
C24B0.5490 (3)0.1204 (3)0.2617 (5)0.0354 (17)0.787 (5)
H24C0.5550140.1229910.3259680.042*0.787 (5)
H24D0.5719030.0938800.2374460.042*0.787 (5)
O1D0.5663 (7)0.1987 (7)0.3159 (11)0.025 (4)0.213 (5)
C21D0.5525 (7)0.1519 (9)0.2718 (12)0.026 (3)0.213 (5)
H21E0.5708950.1227220.2997620.032*0.213 (5)
C22D0.5634 (7)0.1525 (10)0.1741 (12)0.030 (3)0.213 (5)
H22G0.5865010.1808500.1583340.036*0.213 (5)
H22H0.5788620.1199130.1547630.036*0.213 (5)
C23D0.5114 (7)0.1598 (9)0.1336 (12)0.029 (3)0.213 (5)
H23G0.5100870.1447140.0737510.035*0.213 (5)
H23H0.5028860.1964510.1294090.035*0.213 (5)
O3D0.4770 (6)0.1344 (8)0.1910 (11)0.032 (3)0.213 (5)
C24D0.4952 (7)0.1431 (10)0.2782 (12)0.030 (3)0.213 (5)
H24G0.4783180.1733500.3040250.036*0.213 (5)
H24H0.4879870.1132760.3160800.036*0.213 (5)
O4B0.50270 (15)0.32327 (17)0.7952 (2)0.0268 (9)
H4E0.489 (2)0.340 (2)0.752 (3)0.040*
H4F0.5294 (15)0.3086 (19)0.774 (3)0.040*
O5B0.58067 (15)0.27400 (17)0.7083 (2)0.0304 (9)
H5E0.589 (2)0.284 (2)0.657 (2)0.046*
H5F0.6065 (16)0.262 (2)0.736 (3)0.046*
N6B1.0000000.5000000.4494 (7)0.073 (4)
C25B1.0000000.5000000.5259 (8)0.039 (3)
C26B1.0000000.5000000.6212 (7)0.046 (3)
H26D1.0293520.4818900.6422840.069*0.25
H26E1.0010080.5344750.6422840.069*0.25
H26F0.9696400.4836350.6422840.069*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0283 (8)0.0446 (9)0.0350 (6)0.0075 (7)0.0128 (6)0.0002 (6)
F1A0.040 (2)0.046 (2)0.076 (2)0.0179 (18)0.0315 (19)0.0005 (19)
N1A0.016 (2)0.020 (2)0.0188 (17)0.0039 (18)0.0012 (16)0.0001 (17)
N2A0.019 (3)0.022 (3)0.0201 (18)0.004 (2)0.0011 (17)0.0057 (18)
N3A0.015 (2)0.020 (2)0.0203 (17)0.001 (2)0.0018 (17)0.0050 (17)
C1A0.023 (3)0.019 (3)0.018 (2)0.005 (2)0.000 (2)0.000 (2)
C2A0.017 (3)0.020 (3)0.0126 (18)0.002 (2)0.0013 (19)0.0014 (18)
C3A0.017 (3)0.019 (3)0.015 (2)0.002 (2)0.0008 (19)0.0001 (18)
C4A0.017 (3)0.018 (3)0.0109 (19)0.001 (2)0.0007 (18)0.0006 (18)
N4A0.014 (2)0.020 (2)0.0154 (17)0.0072 (19)0.0011 (16)0.0038 (16)
C5A0.017 (3)0.017 (3)0.0150 (19)0.007 (2)0.0028 (18)0.0031 (19)
N5A0.020 (3)0.029 (3)0.028 (2)0.006 (2)0.0035 (19)0.009 (2)
C6A0.015 (3)0.017 (3)0.018 (2)0.004 (2)0.0012 (19)0.0011 (19)
C7A0.019 (3)0.016 (3)0.017 (2)0.002 (2)0.0002 (19)0.0025 (18)
C8A0.013 (3)0.016 (3)0.0152 (19)0.003 (2)0.0012 (18)0.0030 (18)
C9A0.019 (3)0.026 (3)0.0152 (19)0.004 (2)0.001 (2)0.002 (2)
C10A0.032 (3)0.020 (3)0.034 (2)0.001 (3)0.010 (2)0.005 (2)
C11A0.044 (4)0.025 (4)0.051 (3)0.012 (3)0.019 (3)0.003 (3)
C12A0.027 (3)0.034 (4)0.044 (3)0.010 (3)0.018 (3)0.003 (3)
C13A0.019 (3)0.037 (4)0.025 (2)0.001 (3)0.007 (2)0.001 (2)
C14A0.023 (3)0.026 (3)0.016 (2)0.001 (2)0.001 (2)0.001 (2)
O2A0.018 (2)0.028 (2)0.0180 (14)0.0041 (17)0.0020 (14)0.0017 (15)
C15A0.015 (3)0.020 (3)0.020 (2)0.001 (2)0.001 (2)0.001 (2)
C16A0.020 (3)0.023 (3)0.0157 (19)0.008 (2)0.001 (2)0.001 (2)
C17A0.017 (3)0.030 (3)0.021 (2)0.004 (3)0.002 (2)0.004 (2)
C18A0.027 (3)0.031 (4)0.024 (2)0.011 (3)0.003 (2)0.005 (2)
C19A0.021 (3)0.047 (4)0.041 (3)0.000 (3)0.002 (3)0.019 (3)
C20A0.033 (4)0.044 (4)0.045 (3)0.009 (3)0.010 (3)0.017 (3)
O1A0.0143 (19)0.022 (2)0.0254 (16)0.0020 (16)0.0037 (14)0.0069 (15)
C21A0.017 (4)0.023 (4)0.027 (4)0.002 (3)0.006 (3)0.009 (4)
C22A0.027 (4)0.022 (4)0.035 (4)0.000 (3)0.000 (3)0.003 (4)
C23A0.023 (4)0.032 (4)0.050 (5)0.003 (3)0.002 (4)0.002 (4)
O3A0.023 (3)0.031 (3)0.058 (3)0.001 (2)0.001 (2)0.006 (3)
C24A0.023 (4)0.030 (4)0.031 (4)0.003 (3)0.007 (3)0.006 (3)
C21C0.022 (6)0.021 (6)0.028 (6)0.002 (6)0.005 (6)0.005 (6)
C22C0.021 (6)0.022 (6)0.035 (7)0.005 (5)0.000 (6)0.009 (6)
C23C0.024 (6)0.030 (6)0.043 (7)0.002 (5)0.001 (6)0.006 (6)
O3C0.025 (5)0.035 (5)0.050 (5)0.003 (5)0.012 (5)0.004 (5)
C24C0.022 (6)0.030 (6)0.035 (6)0.000 (6)0.008 (6)0.004 (6)
O4A0.024 (2)0.036 (3)0.0221 (16)0.0015 (18)0.0012 (17)0.0049 (16)
O5A0.025 (2)0.061 (3)0.0220 (17)0.013 (2)0.0019 (16)0.0072 (19)
N6A0.108 (9)0.108 (9)0.084 (10)0.0000.0000.000
C25A0.068 (8)0.068 (8)0.060 (9)0.0000.0000.000
C26A0.110 (10)0.110 (10)0.067 (10)0.0000.0000.000
Cl1B0.0316 (8)0.0372 (9)0.0470 (7)0.0096 (7)0.0191 (6)0.0103 (6)
F1B0.026 (2)0.044 (2)0.0611 (19)0.0100 (16)0.0132 (16)0.0082 (17)
N1B0.018 (3)0.022 (2)0.0182 (17)0.0003 (19)0.0031 (16)0.0021 (17)
N2B0.016 (2)0.021 (3)0.0237 (19)0.0019 (19)0.0009 (17)0.0036 (18)
N3B0.014 (2)0.015 (2)0.0209 (17)0.0010 (19)0.0018 (16)0.0016 (17)
C1B0.016 (3)0.022 (3)0.025 (2)0.003 (2)0.002 (2)0.007 (2)
C2B0.018 (3)0.019 (3)0.0125 (18)0.001 (2)0.0006 (19)0.0004 (18)
C3B0.016 (3)0.014 (3)0.013 (2)0.000 (2)0.0005 (18)0.0001 (17)
C4B0.018 (3)0.016 (3)0.017 (2)0.001 (2)0.0005 (19)0.0025 (19)
N4B0.015 (2)0.028 (3)0.0164 (17)0.005 (2)0.0022 (17)0.0016 (17)
C5B0.019 (3)0.018 (3)0.015 (2)0.004 (2)0.0008 (19)0.0008 (19)
N5B0.022 (3)0.031 (3)0.0231 (19)0.007 (2)0.0067 (19)0.0055 (19)
C6B0.018 (3)0.026 (3)0.023 (2)0.005 (2)0.003 (2)0.005 (2)
C7B0.019 (3)0.022 (3)0.020 (2)0.001 (2)0.002 (2)0.005 (2)
C8B0.021 (3)0.019 (3)0.0145 (19)0.004 (2)0.0005 (19)0.0056 (19)
C9B0.018 (3)0.018 (3)0.017 (2)0.002 (2)0.0013 (19)0.0031 (19)
C10B0.019 (3)0.020 (3)0.024 (2)0.003 (2)0.0003 (19)0.0019 (19)
C11B0.029 (3)0.020 (3)0.033 (2)0.007 (2)0.003 (2)0.003 (2)
C12B0.023 (3)0.033 (4)0.030 (2)0.009 (3)0.004 (2)0.004 (2)
C13B0.026 (3)0.023 (3)0.024 (2)0.005 (2)0.003 (2)0.005 (2)
C14B0.024 (3)0.020 (3)0.020 (2)0.001 (2)0.001 (2)0.002 (2)
O2B0.015 (2)0.030 (2)0.0173 (14)0.0087 (16)0.0007 (14)0.0002 (15)
C15B0.012 (3)0.020 (3)0.019 (2)0.001 (2)0.0009 (19)0.000 (2)
C16B0.016 (3)0.024 (3)0.020 (2)0.004 (2)0.001 (2)0.000 (2)
C17B0.020 (3)0.019 (3)0.023 (2)0.004 (2)0.005 (2)0.003 (2)
C18B0.027 (3)0.030 (4)0.024 (2)0.011 (3)0.003 (2)0.001 (2)
C19B0.024 (3)0.036 (4)0.038 (3)0.002 (3)0.007 (3)0.009 (3)
C20B0.037 (4)0.043 (4)0.042 (3)0.016 (3)0.014 (3)0.009 (3)
O1B0.013 (2)0.023 (3)0.022 (3)0.001 (2)0.006 (2)0.008 (2)
C21B0.019 (3)0.022 (3)0.024 (3)0.002 (3)0.002 (2)0.010 (3)
C22B0.020 (3)0.026 (3)0.022 (3)0.002 (3)0.000 (2)0.005 (2)
C23B0.023 (3)0.028 (4)0.032 (3)0.004 (3)0.003 (3)0.003 (3)
O3B0.029 (3)0.025 (3)0.053 (3)0.006 (2)0.008 (2)0.004 (2)
C24B0.026 (4)0.033 (4)0.047 (3)0.002 (3)0.014 (3)0.000 (3)
O1D0.025 (6)0.023 (7)0.027 (7)0.001 (6)0.007 (6)0.006 (6)
C21D0.019 (5)0.027 (5)0.033 (5)0.003 (5)0.005 (5)0.005 (5)
C22D0.023 (6)0.033 (6)0.035 (6)0.005 (6)0.000 (6)0.006 (6)
C23D0.024 (6)0.032 (6)0.031 (6)0.003 (6)0.004 (6)0.001 (6)
O3D0.024 (6)0.036 (6)0.036 (6)0.005 (5)0.001 (5)0.003 (5)
C24D0.022 (6)0.031 (6)0.037 (6)0.001 (5)0.002 (5)0.005 (5)
O4B0.019 (2)0.039 (3)0.0230 (16)0.0001 (18)0.0041 (17)0.0031 (16)
O5B0.021 (2)0.047 (3)0.0224 (17)0.0058 (19)0.0002 (15)0.0103 (17)
N6B0.086 (7)0.086 (7)0.048 (7)0.0000.0000.000
C25B0.037 (5)0.037 (5)0.043 (6)0.0000.0000.000
C26B0.050 (5)0.050 (5)0.039 (6)0.0000.0000.000
Geometric parameters (Å, º) top
Cl1A—C13A1.729 (6)F1B—C12B1.362 (6)
F1A—C12A1.349 (6)N1B—C1B1.315 (6)
N1A—C1A1.315 (6)N1B—C8B1.380 (6)
N1A—C8A1.377 (6)N2B—C2B1.332 (6)
N2A—C2A1.329 (6)N2B—C1B1.355 (6)
N2A—C1A1.340 (6)N3B—C2B1.351 (6)
N3A—C2A1.368 (6)N3B—C9B1.420 (6)
N3A—C9A1.407 (6)N3B—H3B0.8800
N3A—H3A0.8800C1B—H1B0.9500
C1A—H1A0.9500C2B—C3B1.439 (7)
C2A—C3A1.437 (7)C3B—C8B1.407 (6)
C3A—C4A1.394 (6)C3B—C4B1.413 (7)
C3A—C8A1.415 (6)C4B—C5B1.369 (7)
C4A—C5A1.369 (6)C4B—H4B0.9500
C4A—H4A0.9500N4B—C15B1.348 (5)
N4A—C15A1.356 (5)N4B—C5B1.417 (6)
N4A—C5A1.411 (6)N4B—H4B10.8800
N4A—H4A10.8800C5B—C6B1.418 (7)
C5A—C6A1.424 (6)N5B—C18B1.466 (6)
N5A—C20A1.454 (7)N5B—C20B1.472 (7)
N5A—C19A1.467 (6)N5B—C19B1.474 (6)
N5A—C18A1.472 (6)C6B—O1B1.358 (7)
C6A—O1A1.363 (5)C6B—C7B1.375 (7)
C6A—C7A1.373 (6)C6B—O1D1.424 (17)
C7A—C8A1.411 (7)C7B—C8B1.410 (7)
C7A—H7A0.9500C7B—H7B0.9500
C9A—C14A1.396 (7)C9B—C14B1.390 (7)
C9A—C10A1.399 (7)C9B—C10B1.396 (7)
C10A—C11A1.389 (8)C10B—C11B1.391 (7)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.367 (8)C11B—C12B1.370 (7)
C11A—H11A0.9500C11B—H11B0.9500
C12A—C13A1.378 (8)C12B—C13B1.391 (8)
C13A—C14A1.393 (7)C13B—C14B1.383 (7)
C14A—H14A0.9500C14B—H14B0.9500
O2A—C15A1.246 (6)O2B—C15B1.241 (5)
C15A—C16A1.471 (7)C15B—C16B1.483 (7)
C16A—C17A1.322 (6)C16B—C17B1.325 (6)
C16A—H16A0.9500C16B—H16B0.9500
C17A—C18A1.491 (7)C17B—C18B1.489 (7)
C17A—H17A0.9500C17B—H17B0.9500
C18A—H18A0.9900C18B—H18C0.9900
C18A—H18B0.9900C18B—H18D0.9900
C19A—H19A0.9800C19B—H19D0.9800
C19A—H19B0.9800C19B—H19E0.9800
C19A—H19C0.9800C19B—H19F0.9800
C20A—H20A0.9800C20B—H20D0.9800
C20A—H20B0.9800C20B—H20E0.9800
C20A—H20C0.9800C20B—H20F0.9800
O1A—C21C1.43 (6)O1B—C21B1.445 (7)
O1A—C21A1.456 (19)C21B—C24B1.520 (9)
C21A—C22A1.522 (12)C21B—C22B1.521 (8)
C21A—C24A1.534 (10)C21B—H21B1.0000
C21A—H21A1.0000C22B—C23B1.495 (8)
C22A—C23A1.495 (10)C22B—H22C0.9900
C22A—H22A0.9900C22B—H22D0.9900
C22A—H22B0.9900C23B—O3B1.444 (8)
C23A—O3A1.426 (9)C23B—H23C0.9900
C23A—H23A0.9900C23B—H23D0.9900
C23A—H23B0.9900O3B—C24B1.427 (8)
O3A—C24A1.423 (15)C24B—H24C0.9900
C24A—H24A0.9900C24B—H24D0.9900
C24A—H24B0.9900O1D—C21D1.445 (19)
C21C—C22C1.51 (2)C21D—C22D1.508 (19)
C21C—C24C1.53 (2)C21D—C24D1.524 (19)
C21C—H21C1.0000C21D—H21E1.0000
C22C—C23C1.497 (19)C22D—C23D1.509 (19)
C22C—H22E0.9900C22D—H22G0.9900
C22C—H22F0.9900C22D—H22H0.9900
C23C—O3C1.403 (18)C23D—O3D1.420 (18)
C23C—H23E0.9900C23D—H23G0.9900
C23C—H23F0.9900C23D—H23H0.9900
O3C—C24C1.43 (2)O3D—C24D1.424 (18)
C24C—H24E0.9900C24D—H24G0.9900
C24C—H24F0.9900C24D—H24H0.9900
O4A—H4C0.87 (3)O4B—H4E0.87 (3)
O4A—H4D0.86 (3)O4B—H4F0.86 (3)
O5A—H5C0.84 (3)O5B—H5E0.85 (3)
O5A—H5D0.84 (3)O5B—H5F0.85 (3)
N6A—C25A1.174 (17)N6B—C25B1.161 (14)
C25A—C26A1.48 (2)C25B—C26B1.444 (14)
C26A—H26A0.9600C26B—H26D0.9600
C26A—H26B0.9600C26B—H26E0.9600
C26A—H26C0.9600C26B—H26F0.9600
C26A—H26Ai0.9600C26B—H26Div0.9600
C26A—H26Aii0.9600C26B—H26Dv0.9600
C26A—H26Aiii0.9600C26B—H26Dvi0.9600
C26A—H26Bi0.9600C26B—H26Eiv0.9600
C26A—H26Bii0.9600C26B—H26Ev0.9600
C26A—H26Biii0.9600C26B—H26Evi0.9600
C26A—H26Ci0.9599C26B—H26Fiv0.9599
C26A—H26Cii0.9599C26B—H26Fv0.9599
C26A—H26Ciii0.9599C26B—H26Fvi0.9599
Cl1B—C13B1.725 (5)
C1A—N1A—C8A115.3 (4)C2B—N2B—C1B116.1 (4)
C2A—N2A—C1A116.2 (4)C2B—N3B—C9B127.7 (5)
C2A—N3A—C9A128.6 (5)C2B—N3B—H3B116.2
C2A—N3A—H3A115.7C9B—N3B—H3B116.2
C9A—N3A—H3A115.7N1B—C1B—N2B129.3 (5)
N1A—C1A—N2A129.3 (5)N1B—C1B—H1B115.3
N1A—C1A—H1A115.3N2B—C1B—H1B115.3
N2A—C1A—H1A115.3N2B—C2B—N3B119.8 (5)
N2A—C2A—N3A119.1 (5)N2B—C2B—C3B120.9 (5)
N2A—C2A—C3A121.5 (4)N3B—C2B—C3B119.3 (5)
N3A—C2A—C3A119.4 (5)C8B—C3B—C4B118.7 (5)
C4A—C3A—C8A118.9 (5)C8B—C3B—C2B117.2 (5)
C4A—C3A—C2A124.8 (5)C4B—C3B—C2B124.0 (4)
C8A—C3A—C2A116.3 (4)C5B—C4B—C3B120.2 (5)
C5A—C4A—C3A121.6 (5)C5B—C4B—H4B119.9
C5A—C4A—H4A119.2C3B—C4B—H4B119.9
C3A—C4A—H4A119.2C15B—N4B—C5B122.8 (4)
C15A—N4A—C5A122.5 (4)C15B—N4B—H4B1118.6
C15A—N4A—H4A1118.7C5B—N4B—H4B1118.6
C5A—N4A—H4A1118.7C4B—C5B—N4B119.6 (5)
C4A—C5A—N4A121.2 (4)C4B—C5B—C6B120.7 (5)
C4A—C5A—C6A119.2 (5)N4B—C5B—C6B119.6 (5)
N4A—C5A—C6A119.6 (4)C18B—N5B—C20B111.0 (4)
C20A—N5A—C19A110.4 (4)C18B—N5B—C19B110.8 (4)
C20A—N5A—C18A111.4 (4)C20B—N5B—C19B110.6 (4)
C19A—N5A—C18A111.1 (4)O1B—C6B—C7B125.4 (5)
O1A—C6A—C7A125.5 (5)O1B—C6B—C5B114.8 (5)
O1A—C6A—C5A114.1 (4)C7B—C6B—C5B119.7 (5)
C7A—C6A—C5A120.4 (5)C7B—C6B—O1D123.2 (9)
C6A—C7A—C8A119.9 (5)C5B—C6B—O1D113.0 (9)
C6A—C7A—H7A120.1C6B—C7B—C8B119.8 (5)
C8A—C7A—H7A120.1C6B—C7B—H7B120.1
N1A—C8A—C7A119.1 (4)C8B—C7B—H7B120.1
N1A—C8A—C3A121.2 (5)N1B—C8B—C3B121.2 (5)
C7A—C8A—C3A119.7 (5)N1B—C8B—C7B118.4 (4)
C14A—C9A—C10A119.7 (5)C3B—C8B—C7B120.4 (5)
C14A—C9A—N3A122.8 (5)C14B—C9B—C10B119.8 (5)
C10A—C9A—N3A117.4 (5)C14B—C9B—N3B122.8 (5)
C11A—C10A—C9A120.3 (5)C10B—C9B—N3B117.3 (5)
C11A—C10A—H10A119.8C11B—C10B—C9B120.2 (5)
C9A—C10A—H10A119.8C11B—C10B—H10B119.9
C12A—C11A—C10A119.4 (6)C9B—C10B—H10B119.9
C12A—C11A—H11A120.3C12B—C11B—C10B119.0 (5)
C10A—C11A—H11A120.3C12B—C11B—H11B120.5
F1A—C12A—C11A119.2 (6)C10B—C11B—H11B120.5
F1A—C12A—C13A119.6 (5)F1B—C12B—C11B119.7 (5)
C11A—C12A—C13A121.3 (5)F1B—C12B—C13B118.4 (5)
C12A—C13A—C14A120.4 (5)C11B—C12B—C13B121.8 (5)
C12A—C13A—Cl1A119.9 (4)C14B—C13B—C12B119.1 (5)
C14A—C13A—Cl1A119.7 (4)C14B—C13B—Cl1B120.5 (4)
C13A—C14A—C9A118.9 (5)C12B—C13B—Cl1B120.4 (4)
C13A—C14A—H14A120.5C13B—C14B—C9B120.1 (5)
C9A—C14A—H14A120.5C13B—C14B—H14B120.0
O2A—C15A—N4A123.0 (5)C9B—C14B—H14B120.0
O2A—C15A—C16A122.0 (4)O2B—C15B—N4B123.4 (5)
N4A—C15A—C16A114.9 (4)O2B—C15B—C16B121.7 (4)
C17A—C16A—C15A121.6 (5)N4B—C15B—C16B114.9 (4)
C17A—C16A—H16A119.2C17B—C16B—C15B121.7 (4)
C15A—C16A—H16A119.2C17B—C16B—H16B119.2
C16A—C17A—C18A124.9 (5)C15B—C16B—H16B119.2
C16A—C17A—H17A117.5C16B—C17B—C18B124.2 (5)
C18A—C17A—H17A117.5C16B—C17B—H17B117.9
N5A—C18A—C17A110.8 (5)C18B—C17B—H17B117.9
N5A—C18A—H18A109.5N5B—C18B—C17B111.1 (4)
C17A—C18A—H18A109.5N5B—C18B—H18C109.4
N5A—C18A—H18B109.5C17B—C18B—H18C109.4
C17A—C18A—H18B109.5N5B—C18B—H18D109.4
H18A—C18A—H18B108.1C17B—C18B—H18D109.4
N5A—C19A—H19A109.5H18C—C18B—H18D108.0
N5A—C19A—H19B109.5N5B—C19B—H19D109.5
H19A—C19A—H19B109.5N5B—C19B—H19E109.5
N5A—C19A—H19C109.5H19D—C19B—H19E109.5
H19A—C19A—H19C109.5N5B—C19B—H19F109.5
H19B—C19A—H19C109.5H19D—C19B—H19F109.5
N5A—C20A—H20A109.5H19E—C19B—H19F109.5
N5A—C20A—H20B109.5N5B—C20B—H20D109.5
H20A—C20A—H20B109.5N5B—C20B—H20E109.5
N5A—C20A—H20C109.5H20D—C20B—H20E109.5
H20A—C20A—H20C109.5N5B—C20B—H20F109.5
H20B—C20A—H20C109.5H20D—C20B—H20F109.5
C6A—O1A—C21C118.2 (19)H20E—C20B—H20F109.5
C6A—O1A—C21A116.7 (8)C6B—O1B—C21B118.4 (5)
O1A—C21A—C22A111.8 (16)O1B—C21B—C24B110.6 (6)
O1A—C21A—C24A107.7 (13)O1B—C21B—C22B107.4 (5)
C22A—C21A—C24A103.9 (9)C24B—C21B—C22B104.1 (5)
O1A—C21A—H21A111.0O1B—C21B—H21B111.5
C22A—C21A—H21A111.0C24B—C21B—H21B111.5
C24A—C21A—H21A111.0C22B—C21B—H21B111.5
C23A—C22A—C21A103.4 (7)C23B—C22B—C21B102.3 (5)
C23A—C22A—H22A111.1C23B—C22B—H22C111.3
C21A—C22A—H22A111.1C21B—C22B—H22C111.3
C23A—C22A—H22B111.1C23B—C22B—H22D111.3
C21A—C22A—H22B111.1C21B—C22B—H22D111.3
H22A—C22A—H22B109.0H22C—C22B—H22D109.2
O3A—C23A—C22A104.5 (7)O3B—C23B—C22B104.5 (5)
O3A—C23A—H23A110.8O3B—C23B—H23C110.8
C22A—C23A—H23A110.8C22B—C23B—H23C110.8
O3A—C23A—H23B110.8O3B—C23B—H23D110.8
C22A—C23A—H23B110.8C22B—C23B—H23D110.8
H23A—C23A—H23B108.9H23C—C23B—H23D108.9
C24A—O3A—C23A105.0 (8)C24B—O3B—C23B106.0 (5)
O3A—C24A—C21A105.6 (11)O3B—C24B—C21B107.5 (5)
O3A—C24A—H24A110.6O3B—C24B—H24C110.2
C21A—C24A—H24A110.6C21B—C24B—H24C110.2
O3A—C24A—H24B110.6O3B—C24B—H24D110.2
C21A—C24A—H24B110.6C21B—C24B—H24D110.2
H24A—C24A—H24B108.7H24C—C24B—H24D108.5
O1A—C21C—C22C117 (4)C6B—O1D—C21D119.5 (15)
O1A—C21C—C24C108 (4)O1D—C21D—C22D113.5 (19)
C22C—C21C—C24C103.6 (18)O1D—C21D—C24D110.3 (17)
O1A—C21C—H21C109.4C22D—C21D—C24D104.5 (13)
C22C—C21C—H21C109.4O1D—C21D—H21E109.4
C24C—C21C—H21C109.4C22D—C21D—H21E109.4
C23C—C22C—C21C105.9 (16)C24D—C21D—H21E109.4
C23C—C22C—H22E110.6C21D—C22D—C23D103.3 (14)
C21C—C22C—H22E110.6C21D—C22D—H22G111.1
C23C—C22C—H22F110.6C23D—C22D—H22G111.1
C21C—C22C—H22F110.6C21D—C22D—H22H111.1
H22E—C22C—H22F108.7C23D—C22D—H22H111.1
O3C—C23C—C22C108.2 (15)H22G—C22D—H22H109.1
O3C—C23C—H23E110.0O3D—C23D—C22D105.4 (14)
C22C—C23C—H23E110.0O3D—C23D—H23G110.7
O3C—C23C—H23F110.0C22D—C23D—H23G110.7
C22C—C23C—H23F110.0O3D—C23D—H23H110.7
H23E—C23C—H23F108.4C22D—C23D—H23H110.7
C23C—O3C—C24C109.3 (17)H23G—C23D—H23H108.8
O3C—C24C—C21C105 (2)C23D—O3D—C24D106.3 (14)
O3C—C24C—H24E110.7O3D—C24D—C21D107.2 (14)
C21C—C24C—H24E110.7O3D—C24D—H24G110.3
O3C—C24C—H24F110.7C21D—C24D—H24G110.3
C21C—C24C—H24F110.7O3D—C24D—H24H110.3
H24E—C24C—H24F108.8C21D—C24D—H24H110.3
H4C—O4A—H4D104 (5)H24G—C24D—H24H108.5
H5C—O5A—H5D101 (6)H4E—O4B—H4F107 (5)
N6A—C25A—C26A180.0H5E—O5B—H5F110 (5)
C25A—C26A—H26A109.5N6B—C25B—C26B180.0
C25A—C26A—H26B109.5C25B—C26B—H26D109.5
H26A—C26A—H26B109.5C25B—C26B—H26E109.5
C25A—C26A—H26C109.5H26D—C26B—H26E109.5
H26A—C26A—H26C109.5C25B—C26B—H26F109.5
H26B—C26A—H26C109.5H26D—C26B—H26F109.5
C25A—C26A—H26Ai109.471 (1)H26E—C26B—H26F109.5
C25A—C26A—H26Aii109.5C25B—C26B—H26Div109.469 (1)
C25A—C26A—H26Aiii109.471 (1)C25B—C26B—H26Dv109.469 (1)
C25A—C26A—H26Bi109.5C25B—C26B—H26Dvi109.469 (2)
H26Ai—C26A—H26Bi109.5C25B—C26B—H26Eiv109.467 (2)
C25A—C26A—H26Bii109.471 (1)H26Div—C26B—H26Eiv109.5
H26Aii—C26A—H26Bii109.5C25B—C26B—H26Ev109.467 (1)
C25A—C26A—H26Biii109.471 (1)H26Dv—C26B—H26Ev109.5
H26Aiii—C26A—H26Biii109.5C25B—C26B—H26Evi109.467 (1)
C25A—C26A—H26Ci109.473 (1)H26Dvi—C26B—H26Evi109.5
H26Ai—C26A—H26Ci109.5C25B—C26B—H26Fiv109.470 (1)
H26Bi—C26A—H26Ci109.5H26Div—C26B—H26Fiv109.5
C25A—C26A—H26Cii109.5H26Eiv—C26B—H26Fiv109.5
H26Aii—C26A—H26Cii109.5C25B—C26B—H26Fv109.470 (2)
H26Bii—C26A—H26Cii109.5H26Dv—C26B—H26Fv109.5
C25A—C26A—H26Ciii109.5H26Ev—C26B—H26Fv109.5
H26Aiii—C26A—H26Ciii109.5C25B—C26B—H26Fvi109.470 (1)
H26Biii—C26A—H26Ciii109.5H26Dvi—C26B—H26Fvi109.5
C1B—N1B—C8B115.2 (4)H26Evi—C26B—H26Fvi109.5
C8A—N1A—C1A—N2A3.0 (7)C1B—N2B—C2B—N3B175.9 (4)
C2A—N2A—C1A—N1A0.3 (7)C1B—N2B—C2B—C3B3.6 (6)
C1A—N2A—C2A—N3A176.9 (4)C9B—N3B—C2B—N2B2.0 (7)
C1A—N2A—C2A—C3A3.0 (6)C9B—N3B—C2B—C3B178.6 (4)
C9A—N3A—C2A—N2A3.6 (7)N2B—C2B—C3B—C8B3.9 (6)
C9A—N3A—C2A—C3A176.5 (4)N3B—C2B—C3B—C8B175.6 (4)
N2A—C2A—C3A—C4A173.4 (4)N2B—C2B—C3B—C4B173.7 (4)
N3A—C2A—C3A—C4A6.6 (7)N3B—C2B—C3B—C4B6.9 (6)
N2A—C2A—C3A—C8A3.4 (6)C8B—C3B—C4B—C5B0.2 (6)
N3A—C2A—C3A—C8A176.5 (4)C2B—C3B—C4B—C5B177.7 (4)
C8A—C3A—C4A—C5A0.2 (7)C3B—C4B—C5B—N4B174.6 (4)
C2A—C3A—C4A—C5A177.0 (4)C3B—C4B—C5B—C6B5.2 (7)
C3A—C4A—C5A—N4A175.0 (4)C15B—N4B—C5B—C4B43.7 (7)
C3A—C4A—C5A—C6A4.5 (7)C15B—N4B—C5B—C6B136.0 (5)
C15A—N4A—C5A—C4A45.2 (7)C4B—C5B—C6B—O1B168.8 (5)
C15A—N4A—C5A—C6A134.4 (5)N4B—C5B—C6B—O1B11.5 (7)
C4A—C5A—C6A—O1A174.7 (4)C4B—C5B—C6B—C7B6.5 (7)
N4A—C5A—C6A—O1A5.8 (6)N4B—C5B—C6B—C7B173.2 (4)
C4A—C5A—C6A—C7A5.1 (7)C4B—C5B—C6B—O1D164.5 (9)
N4A—C5A—C6A—C7A174.4 (4)N4B—C5B—C6B—O1D15.2 (10)
O1A—C6A—C7A—C8A178.8 (4)O1B—C6B—C7B—C8B172.3 (5)
C5A—C6A—C7A—C8A1.0 (7)C5B—C6B—C7B—C8B2.4 (7)
C1A—N1A—C8A—C7A178.5 (4)O1D—C6B—C7B—C8B158.1 (9)
C1A—N1A—C8A—C3A2.3 (6)C1B—N1B—C8B—C3B1.4 (6)
C6A—C7A—C8A—N1A177.1 (4)C1B—N1B—C8B—C7B179.2 (4)
C6A—C7A—C8A—C3A3.8 (6)C4B—C3B—C8B—N1B176.5 (4)
C4A—C3A—C8A—N1A176.4 (4)C2B—C3B—C8B—N1B1.2 (6)
C2A—C3A—C8A—N1A0.6 (6)C4B—C3B—C8B—C7B4.2 (6)
C4A—C3A—C8A—C7A4.4 (6)C2B—C3B—C8B—C7B178.1 (4)
C2A—C3A—C8A—C7A178.6 (4)C6B—C7B—C8B—N1B177.8 (4)
C2A—N3A—C9A—C14A31.5 (7)C6B—C7B—C8B—C3B2.9 (7)
C2A—N3A—C9A—C10A151.7 (5)C2B—N3B—C9B—C14B32.6 (7)
C14A—C9A—C10A—C11A1.7 (8)C2B—N3B—C9B—C10B149.8 (4)
N3A—C9A—C10A—C11A178.6 (5)C14B—C9B—C10B—C11B0.4 (7)
C9A—C10A—C11A—C12A0.8 (9)N3B—C9B—C10B—C11B177.3 (4)
C10A—C11A—C12A—F1A178.5 (5)C9B—C10B—C11B—C12B0.5 (7)
C10A—C11A—C12A—C13A0.5 (9)C10B—C11B—C12B—F1B178.2 (4)
F1A—C12A—C13A—C14A178.0 (5)C10B—C11B—C12B—C13B0.2 (8)
C11A—C12A—C13A—C14A1.0 (9)F1B—C12B—C13B—C14B178.7 (4)
F1A—C12A—C13A—Cl1A2.0 (8)C11B—C12B—C13B—C14B0.3 (8)
C11A—C12A—C13A—Cl1A179.0 (5)F1B—C12B—C13B—Cl1B1.2 (7)
C12A—C13A—C14A—C9A0.1 (7)C11B—C12B—C13B—Cl1B179.6 (4)
Cl1A—C13A—C14A—C9A179.9 (4)C12B—C13B—C14B—C9B0.4 (7)
C10A—C9A—C14A—C13A1.2 (7)Cl1B—C13B—C14B—C9B179.5 (4)
N3A—C9A—C14A—C13A177.9 (4)C10B—C9B—C14B—C13B0.1 (7)
C5A—N4A—C15A—O2A3.5 (8)N3B—C9B—C14B—C13B177.6 (4)
C5A—N4A—C15A—C16A175.4 (4)C5B—N4B—C15B—O2B4.9 (8)
O2A—C15A—C16A—C17A5.0 (8)C5B—N4B—C15B—C16B175.8 (4)
N4A—C15A—C16A—C17A173.9 (5)O2B—C15B—C16B—C17B5.6 (8)
C15A—C16A—C17A—C18A178.0 (5)N4B—C15B—C16B—C17B175.2 (5)
C20A—N5A—C18A—C17A166.2 (4)C15B—C16B—C17B—C18B179.2 (5)
C19A—N5A—C18A—C17A70.3 (5)C20B—N5B—C18B—C17B166.4 (5)
C16A—C17A—C18A—N5A112.2 (6)C19B—N5B—C18B—C17B70.3 (6)
C7A—C6A—O1A—C21C12 (2)C16B—C17B—C18B—N5B113.4 (6)
C5A—C6A—O1A—C21C167 (2)C7B—C6B—O1B—C21B6.0 (8)
C7A—C6A—O1A—C21A6.8 (11)C5B—C6B—O1B—C21B168.9 (5)
C5A—C6A—O1A—C21A173.0 (10)C6B—O1B—C21B—C24B86.5 (7)
C6A—O1A—C21A—C22A81.6 (14)C6B—O1B—C21B—C22B160.5 (5)
C6A—O1A—C21A—C24A164.8 (10)O1B—C21B—C22B—C23B93.5 (6)
O1A—C21A—C22A—C23A128.0 (11)C24B—C21B—C22B—C23B23.8 (7)
C24A—C21A—C22A—C23A12.1 (18)C21B—C22B—C23B—O3B38.2 (6)
C21A—C22A—C23A—O3A33.6 (13)C22B—C23B—O3B—C24B38.4 (7)
C22A—C23A—O3A—C24A43.4 (10)C23B—O3B—C24B—C21B22.5 (7)
C23A—O3A—C24A—C21A35.0 (15)O1B—C21B—C24B—O3B113.5 (6)
O1A—C21A—C24A—O3A105.5 (13)C22B—C21B—C24B—O3B1.6 (7)
C22A—C21A—C24A—O3A13.2 (19)C7B—C6B—O1D—C21D19 (2)
C6A—O1A—C21C—C22C75 (4)C5B—C6B—O1D—C21D176.1 (14)
C6A—O1A—C21C—C24C168 (2)C6B—O1D—C21D—C22D59 (2)
O1A—C21C—C22C—C23C133 (3)C6B—O1D—C21D—C24D175.9 (15)
C24C—C21C—C22C—C23C15 (5)O1D—C21D—C22D—C23D104 (2)
C21C—C22C—C23C—O3C1 (4)C24D—C21D—C22D—C23D16 (2)
C22C—C23C—O3C—C24C19 (3)C21D—C22D—C23D—O3D33 (2)
C23C—O3C—C24C—C21C28 (5)C22D—C23D—O3D—C24D37 (2)
O1A—C21C—C24C—O3C150 (4)C23D—O3D—C24D—C21D27 (3)
C22C—C21C—C24C—O3C26 (6)O1D—C21D—C24D—O3D128 (2)
C8B—N1B—C1B—N2B1.9 (7)C22D—C21D—C24D—O3D5 (3)
C2B—N2B—C1B—N1B0.7 (7)
Symmetry codes: (i) x+1, y, z; (ii) y+1/2, x1/2, z; (iii) y+1/2, x+1/2, z; (iv) x+2, y+1, z; (v) y+3/2, x1/2, z; (vi) y+1/2, x+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4A—H4A1···O4Bvii0.881.942.804 (5)166
N3A—H3A···O2Aviii0.882.223.088 (5)167
O4A—H4C···N5A0.85 (5)1.97 (5)2.816 (6)173 (4)
O4A—H4D···O5A0.86 (5)1.91 (5)2.759 (6)169 (5)
O5A—H5C···O2A0.85 (3)2.00 (4)2.844 (4)174 (5)
O5A—H5D···N1Bviii0.83 (5)1.98 (5)2.775 (6)161 (5)
C4A—H4A···O2Aviii0.952.313.246 (6)168
C16A—H16A···O4Bvii0.952.413.183 (6)139
C22A—H22A···O3Avi0.992.403.353 (13)162
C24A—H24A···O5Bvii0.992.503.388 (14)150
N4B—H4B1···O4Aix0.881.962.820 (5)167
N3B—H3B···O2Bx0.882.263.123 (5)166
O4B—H4E···N5B0.87 (5)1.95 (5)2.811 (5)175 (6)
O4B—H4F···O5B0.86 (4)1.91 (4)2.756 (5)169 (4)
O5B—H5E···O2B0.85 (4)1.98 (3)2.828 (4)173 (5)
O5B—H5F···N1Ax0.86 (4)1.95 (4)2.794 (5)169 (5)
C4B—H4B···O2Bx0.952.343.280 (6)169
C16B—H16B···O4Aix0.952.423.197 (6)139
C22B—H22D···O5Aix0.992.433.160 (8)130
C24B—H24D···O3Biii0.992.573.455 (9)149
Symmetry codes: (iii) y+1/2, x+1/2, z; (vi) y+1/2, x+3/2, z; (vii) x+1/2, y+1/2, z1; (viii) y+1, x+1, z; (ix) x1/2, y+1/2, z; (x) y+1, x+1, z1.
 

Acknowledgements

The authors acknowledge funding for this work provided by the Sao Paulo Research Foundation (FAPESP) (grant Nos. 2015/15456-5 and 2015/05685-7).

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