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

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105037558/gg1291sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105037558/gg1291Isup2.hkl
Contains datablock I

CCDC reference: 294350

Comment top

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

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

All the bond lengths and bond angles are in the normal range, and the observed results distinguish clearly between the COcarbonyl and C—Ohydroxy bonds in the carboxylic acid groups. The short O—H···O hydrogen-bonding distances, within the range 2.454–2.530 Å, involving O4 and O5 are consistent with the positively charged hydronium identity of these species (Jeffrey, 1997). Evidently, the bifurcated N—H···Cl interactions are much weaker than the H3O+···Cl interactions (Table 2). The apparent optimization of the hydrogen-bonding scheme leads to a somewhat inefficient crystal packing of relatively low density, which contains two solvent-accessible voids of ca 80 Å3 that are centered along the interface between the hydrogen-bonded layers at (0.49, 0.22, 0.18) and (0.51, 0.72, 0.82). The terminal isopropyl groups that point into these voids reveal some disorder, reflected in the large-amplitude displacement ellipsoids of their respective atoms (particularly the C17C–C19C fragment). The total residual electron density in the void spaces was assessed to be ten electrons per unit cell (Spek, 2003), which is consistent with the rather minor conformational disorder in the structure. A survey of the Cambridge Structural Database (Allen, 2002) indicates that no structures of similar composition (cyclohexane carbonyl and phenylalanine residues joined through an amide bond) and connectivity have been reported as yet. Multicomponent supramolecular assemblies sustained simultaneously by (COOH)2 cyclic dimeric and N—H···Cl···H—N hydrogen bonds have not been found either, although separate appearances of these two synthons are quite abundant in organic crystals (Allen, 2002; Chang et al., 1993; Chekmenev et al., 2004).

Experimental top

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

Refinement top

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

Computing details top

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

Figures top
[Figure 1] Fig. 1. Compound (I), with the atom-labeling scheme. Displacement ellipsoids are shown at the 50% probability level; the four crystallographically independent molecules of nateglinide are denoted AD.
[Figure 2] Fig. 2. The self-assembled multicomponent asymmetric unit with hydrogen bonding through the COOH dimers and the two chloride ion bridges. For clarity, only H atoms that are involved in hydrogen bonds (dashed lines) are shown. [In the online version of the journal, the hydrogen bonds involving O and Cl atoms are denoted by red and blue dashed lines, respectively. Online color code: Cl green, O red, N blue, C gray, H white.]
[Figure 3] Fig. 3. A face-on illustration of the continuous hydrogen-bonded networks normal to (100), showing further aggregation of the organic tetramers into two-dimensional arrays by cross-linking through the hydronium ions. For clarity, molecules are represented only by their central C—C(COOH)—NH—CO—C fragment; the hydronium and chloride ions are represented by small spheres. [In the online version of the journal, the hydrogen bonds involving O and Cl atoms are denoted by red and blue dashed lines, respectively. Online color code: Cl green, O red, N blue, C black.]
[Figure 4] Fig. 4. The crystal packing, viewed down (001), showing alternating hydrophilic zones (within the hydrogen-bonded layers) and hydrophobic zones (between the layers). The molecules are shown as a stick diagram, except for the hydronium and chloride ions, which are represented by small spheres.
hydronium bis[(-)-N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine] chloride top
Crystal data top
H3O+·2C19H27NO3·ClF(000) = 1488
Mr = 689.31Dx = 1.152 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8475 reflections
a = 14.0121 (2) Åθ = 1.6–27.9°
b = 19.6631 (3) ŵ = 0.14 mm1
c = 15.3773 (2) ÅT = 110 K
β = 110.2998 (8)°Prism, colorless
V = 3973.62 (10) Å30.35 × 0.30 × 0.20 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
11365 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
Graphite monochromatorθmax = 27.9°, θmin = 1.6°
Detector resolution: 56 microns pixels mm-1h = 1818
ϕ and ω scansk = 2523
29123 measured reflectionsl = 2019
15992 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.055 w = 1/[σ2(Fo2) + (0.0461P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115(Δ/σ)max = 0.012
S = 1.03Δρmax = 0.41 e Å3
15992 reflectionsΔρmin = 0.24 e Å3
931 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
15 restraintsExtinction coefficient: 0.0041 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 6258 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.01 (4)
Crystal data top
H3O+·2C19H27NO3·ClV = 3973.62 (10) Å3
Mr = 689.31Z = 4
Monoclinic, P21Mo Kα radiation
a = 14.0121 (2) ŵ = 0.14 mm1
b = 19.6631 (3) ÅT = 110 K
c = 15.3773 (2) Å0.35 × 0.30 × 0.20 mm
β = 110.2998 (8)°
Data collection top
Nonius KappaCCD
diffractometer
11365 reflections with I > 2σ(I)
29123 measured reflectionsRint = 0.071
15992 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115Δρmax = 0.41 e Å3
S = 1.03Δρmin = 0.24 e Å3
15992 reflectionsAbsolute structure: Flack (1983), 6258 Friedel pairs
931 parametersAbsolute structure parameter: 0.01 (4)
15 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
O1A0.20872 (17)0.44495 (13)0.26843 (15)0.0421 (6)
O2A0.03948 (15)0.43870 (11)0.20075 (13)0.0274 (5)
HO2A0.039 (4)0.443 (3)0.2621 (18)0.115 (19)*
O3A0.05653 (16)0.54137 (10)0.04352 (14)0.0286 (5)
N1A0.04733 (19)0.42829 (13)0.03008 (16)0.0243 (5)
HN1A0.012 (2)0.3881 (12)0.005 (2)0.039 (9)*
C1A0.3361 (2)0.36816 (19)0.0582 (2)0.0395 (8)
H1A0.36740.39310.11370.047*
C2A0.3864 (3)0.3606 (2)0.0041 (3)0.0492 (10)
H2A0.45150.38060.00830.059*
C3A0.3419 (3)0.32414 (18)0.0844 (3)0.0468 (10)
H3A0.37640.31870.12740.056*
C4A0.2479 (3)0.29565 (18)0.1023 (3)0.0506 (10)
H4A0.21710.27070.15800.061*
C5A0.1966 (3)0.30299 (17)0.0390 (2)0.0410 (9)
H5A0.13180.28260.05130.049*
C6A0.2410 (2)0.33995 (16)0.0410 (2)0.0300 (7)
C7A0.1878 (2)0.34934 (15)0.1109 (2)0.0281 (7)
H7E0.23710.34110.17400.034*
H7F0.13260.31530.09880.034*
C8A0.1427 (2)0.42098 (15)0.1068 (2)0.0269 (7)
H8A0.19230.45420.09730.032*
C9A0.1311 (2)0.43678 (15)0.1994 (2)0.0284 (7)
C10A0.0060 (2)0.48933 (15)0.00553 (19)0.0239 (6)
C11A0.1012 (2)0.49611 (15)0.06109 (19)0.0249 (6)
H11A0.10680.54150.09190.030*
C12A0.1356 (2)0.44242 (15)0.13777 (19)0.0278 (7)
H12E0.09080.44400.17540.033*
H12F0.12960.39660.10960.033*
C13A0.2456 (2)0.45471 (16)0.2002 (2)0.0294 (7)
H13E0.26700.41800.24710.035*
H13F0.24970.49830.23350.035*
C14A0.3185 (2)0.45692 (15)0.1459 (2)0.0297 (7)
H14A0.31210.41190.11400.036*
C15A0.2833 (2)0.51013 (17)0.0694 (2)0.0316 (7)
H15E0.32900.50950.03270.038*
H15F0.28750.55580.09760.038*
C16A0.1738 (2)0.49665 (17)0.0054 (2)0.0304 (7)
H16E0.17040.45230.02600.036*
H16F0.15240.53240.04290.036*
C17A0.4309 (2)0.46328 (17)0.2094 (2)0.0333 (7)
H17A0.44480.42560.25580.040*
C18A0.5035 (3)0.45362 (19)0.1550 (2)0.0425 (8)
H18E0.49940.49330.11530.064*
H18F0.48410.41270.11640.064*
H18G0.57340.44870.19850.064*
C19A0.4570 (3)0.53024 (19)0.2639 (3)0.0475 (9)
H19E0.52890.53000.30340.071*
H19F0.41460.53500.30260.071*
H19G0.44400.56850.22040.071*
O1B0.32721 (16)0.51923 (11)0.15757 (16)0.0371 (5)
O2B0.15894 (15)0.51443 (10)0.23166 (14)0.0261 (4)
HO2B0.162 (4)0.4669 (11)0.221 (3)0.105 (18)*
O3B0.11424 (15)0.65168 (10)0.14528 (13)0.0270 (5)
N1B0.14367 (18)0.64547 (12)0.27942 (17)0.0232 (5)
HN1B0.112 (2)0.6397 (17)0.3412 (13)0.041 (10)*
C1B0.4164 (2)0.72744 (16)0.2624 (2)0.0314 (7)
H1B0.45800.70450.20820.038*
C2B0.4425 (3)0.79193 (17)0.2813 (2)0.0379 (8)
H2B0.50260.81270.24050.045*
C3B0.3814 (3)0.82683 (16)0.3594 (2)0.0366 (8)
H3B0.39890.87150.37190.044*
C4B0.2949 (3)0.79557 (16)0.4189 (2)0.0354 (8)
H4B0.25290.81890.47270.042*
C5B0.2689 (2)0.73009 (15)0.4003 (2)0.0286 (7)
H5B0.20930.70900.44140.034*
C6B0.3299 (2)0.69570 (14)0.32204 (19)0.0241 (6)
C7B0.3057 (2)0.62345 (15)0.30217 (19)0.0249 (6)
H7I0.37020.59790.27510.030*
H7J0.26580.60120.36140.030*
C8B0.2457 (2)0.61938 (14)0.23556 (19)0.0220 (6)
H8B0.28110.64790.17980.026*
C9B0.2459 (2)0.54571 (15)0.2046 (2)0.0242 (6)
C10B0.0818 (2)0.65723 (14)0.2319 (2)0.0248 (6)
C11B0.0260 (2)0.67602 (15)0.2880 (2)0.0270 (7)
H11B0.02880.68490.35290.032*
C12B0.0970 (2)0.61580 (16)0.2913 (2)0.0342 (7)
H12I0.07250.57490.31470.041*
H12J0.09650.60590.22800.041*
C13B0.2057 (2)0.63242 (16)0.3548 (2)0.0361 (8)
H13I0.20700.63760.41930.043*
H13J0.25110.59410.35370.043*
C14B0.2458 (2)0.69762 (17)0.3254 (2)0.0316 (7)
H14B0.24680.68930.26160.038*
C15B0.1719 (2)0.75633 (16)0.3175 (2)0.0356 (8)
H15I0.19630.79690.29340.043*
H15J0.17120.76750.38010.043*
C16B0.0632 (2)0.73996 (16)0.2538 (2)0.0332 (7)
H16I0.01770.77860.25340.040*
H16J0.06190.73290.18970.040*
C17B0.3558 (2)0.71495 (19)0.3867 (2)0.0428 (9)
H17B0.37390.75880.36340.051*
C18B0.3687 (3)0.7256 (2)0.4893 (2)0.0569 (11)
H18I0.35650.68250.51580.085*
H18J0.31980.75970.49410.085*
H18K0.43800.74120.52340.085*
C19B0.4309 (3)0.6619 (2)0.3788 (3)0.0535 (10)
H19I0.41980.61930.40690.080*
H19J0.50040.67800.41120.080*
H19K0.42090.65430.31330.080*
O1C0.04299 (15)0.44772 (11)0.37335 (13)0.0308 (5)
O2C0.21337 (17)0.44630 (13)0.43949 (15)0.0411 (6)
HO2C0.207 (3)0.444 (2)0.3787 (15)0.070 (13)*
O3C0.00117 (16)0.33903 (10)0.51650 (15)0.0338 (5)
N1C0.01385 (19)0.45147 (12)0.53748 (16)0.0243 (5)
HN1C0.016 (2)0.4942 (11)0.527 (2)0.029 (8)*
C1C0.2428 (3)0.56600 (18)0.7503 (3)0.0436 (9)
H1C0.26770.60170.72240.052*
C2C0.2559 (3)0.5687 (2)0.8456 (3)0.0534 (11)
H2C0.29160.60600.88170.064*
C3C0.2190 (3)0.5196 (2)0.8868 (3)0.0576 (11)
H3C0.22630.52320.95040.069*
C4C0.1712 (3)0.4651 (2)0.8357 (2)0.0563 (11)
H4C0.14630.42980.86440.068*
C5C0.1583 (3)0.46028 (19)0.7412 (2)0.0446 (9)
H5C0.12490.42170.70680.054*
C6C0.1932 (2)0.51051 (18)0.6977 (2)0.0354 (8)
C7C0.1818 (2)0.50885 (17)0.5955 (2)0.0327 (7)
H7CM0.14960.55190.56630.039*
H7CN0.25040.50690.59090.039*
C8C0.1191 (2)0.44961 (16)0.54051 (19)0.0261 (6)
H8C0.15060.40650.57200.031*
C9C0.1211 (2)0.44808 (15)0.4422 (2)0.0274 (7)
C10C0.0422 (2)0.39503 (15)0.52003 (19)0.0253 (6)
C11C0.1536 (2)0.40073 (15)0.50325 (18)0.0258 (7)
H11C0.17700.35470.51500.031*
C12C0.1850 (2)0.45091 (17)0.5647 (2)0.0316 (7)
H12M0.14920.43970.63080.038*
H12N0.16560.49770.55360.038*
C13C0.2999 (2)0.44710 (18)0.5425 (2)0.0351 (8)
H13M0.31770.40120.55850.042*
H13N0.31960.48040.58160.042*
C14C0.3602 (2)0.46156 (17)0.4410 (2)0.0321 (7)
H14C0.34170.50880.42870.039*
C15C0.3254 (2)0.41472 (18)0.3786 (2)0.0369 (8)
H15M0.34570.36750.38610.044*
H15N0.36030.42810.31320.044*
C16C0.2107 (2)0.41713 (18)0.4005 (2)0.0335 (8)
H16M0.19100.46300.38620.040*
H16N0.19150.38380.36120.040*
C17C0.4762 (2)0.4618 (2)0.4195 (2)0.0440 (9)
H17C0.49020.49690.46060.053*
C18C0.5335 (3)0.4844 (2)0.3187 (3)0.0553 (11)
H18M0.52850.44860.27600.083*
H18N0.50320.52640.30590.083*
H18P0.60530.49230.31010.083*
C19C0.5195 (3)0.3964 (2)0.4385 (4)0.0749 (14)
H19M0.59230.40220.42740.112*
H19N0.48440.38310.50330.112*
H19P0.51020.36090.39750.112*
O1D0.18376 (15)0.38516 (10)0.17923 (13)0.0273 (5)
O2D0.35411 (16)0.39201 (11)0.11892 (16)0.0382 (5)
HO2D0.336 (3)0.4370 (11)0.139 (2)0.063 (12)*
O3D0.18841 (14)0.24624 (10)0.28940 (13)0.0256 (4)
N1D0.18444 (18)0.24963 (12)0.14512 (16)0.0225 (5)
HN1D0.144 (2)0.2499 (16)0.1089 (18)0.030 (8)*
C1D0.4500 (2)0.18168 (16)0.0122 (2)0.0313 (7)
H1D0.48400.20750.02040.038*
C2D0.4843 (2)0.11683 (17)0.0433 (2)0.0360 (7)
H2D0.54140.09850.03160.043*
C3D0.4362 (3)0.07918 (18)0.0907 (2)0.0421 (9)
H3D0.46070.03510.11250.051*
C4D0.3518 (3)0.10526 (17)0.1069 (2)0.0388 (8)
H4D0.31800.07890.13920.047*
C5D0.3171 (2)0.17015 (16)0.0756 (2)0.0329 (7)
H5D0.25940.18800.08660.039*
C6D0.3661 (2)0.20907 (15)0.02839 (18)0.0251 (6)
C7D0.3299 (2)0.28009 (15)0.00509 (18)0.0248 (6)
H7DQ0.38840.31180.01630.030*
H7DR0.27950.29470.02300.030*
C8D0.2813 (2)0.28467 (15)0.11121 (18)0.0232 (6)
H8D0.32830.26300.13930.028*
C9D0.2670 (2)0.35912 (15)0.14078 (19)0.0244 (6)
C10D0.1399 (2)0.23607 (14)0.23494 (19)0.0226 (6)
C11D0.0321 (2)0.21081 (15)0.26960 (19)0.0250 (6)
H11D0.01800.19330.33390.030*
C12D0.0093 (2)0.15309 (15)0.2134 (2)0.0285 (7)
H12Q0.02160.16850.14920.034*
H12R0.05480.11410.21100.034*
C13D0.1017 (2)0.13120 (15)0.2588 (2)0.0286 (7)
H13Q0.11290.11450.32230.034*
H13R0.11630.09330.22280.034*
C14D0.1744 (2)0.19011 (15)0.2632 (2)0.0278 (7)
H14D0.15910.20670.19830.033*
C15D0.1517 (2)0.24840 (16)0.3181 (2)0.0319 (7)
H15Q0.19690.28720.31870.038*
H15R0.16640.23370.38300.038*
C16D0.0401 (2)0.27181 (15)0.2769 (2)0.0281 (7)
H16Q0.02710.29150.21460.034*
H16R0.02710.30750.31680.034*
C17D0.2861 (2)0.16681 (16)0.2990 (2)0.0337 (7)
H17D0.28920.12470.26370.040*
C18D0.3574 (3)0.2185 (2)0.2783 (3)0.0559 (10)
H18Q0.35900.26040.31340.084*
H18R0.33270.22880.21180.084*
H18S0.42620.19940.29640.084*
C19D0.3261 (3)0.1474 (2)0.4010 (2)0.0473 (9)
H19Q0.39260.12530.41590.071*
H19R0.27840.11600.41390.071*
H19S0.33330.18840.43900.071*
O40.10227 (16)0.73167 (11)0.54298 (14)0.0275 (5)
HO4A0.061 (2)0.7705 (14)0.516 (2)0.049 (10)*
HO4B0.136 (4)0.730 (3)0.6089 (15)0.12 (2)*
HO4C0.051 (3)0.6968 (17)0.532 (3)0.076 (14)*
O50.03395 (17)0.15067 (11)0.02283 (15)0.0288 (5)
HO5A0.006 (2)0.1901 (14)0.021 (3)0.054 (11)*
HO5B0.060 (3)0.159 (2)0.072 (2)0.094 (16)*
HO5C0.003 (3)0.1080 (13)0.031 (2)0.055 (11)*
Cl10.04404 (6)0.61402 (4)0.49921 (5)0.02937 (17)
Cl20.07094 (6)0.27751 (4)0.00425 (5)0.02868 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0263 (13)0.0662 (17)0.0321 (12)0.0028 (12)0.0081 (11)0.0076 (12)
O2A0.0239 (12)0.0323 (12)0.0271 (11)0.0028 (9)0.0102 (9)0.0013 (9)
O3A0.0330 (12)0.0197 (11)0.0340 (12)0.0024 (9)0.0127 (10)0.0017 (9)
N1A0.0302 (15)0.0210 (13)0.0240 (12)0.0007 (11)0.0123 (11)0.0010 (10)
C1A0.0308 (19)0.050 (2)0.0349 (18)0.0010 (16)0.0083 (16)0.0041 (16)
C2A0.035 (2)0.063 (3)0.058 (2)0.0012 (18)0.0262 (19)0.000 (2)
C3A0.056 (2)0.035 (2)0.070 (3)0.0008 (17)0.047 (2)0.0057 (18)
C4A0.071 (3)0.036 (2)0.058 (2)0.0175 (19)0.040 (2)0.0197 (18)
C5A0.047 (2)0.0318 (18)0.054 (2)0.0117 (16)0.0288 (19)0.0107 (16)
C6A0.0293 (18)0.0245 (16)0.0394 (18)0.0013 (13)0.0160 (15)0.0038 (14)
C7A0.0279 (17)0.0292 (17)0.0290 (15)0.0034 (13)0.0120 (14)0.0051 (13)
C8A0.0278 (17)0.0277 (16)0.0277 (15)0.0024 (13)0.0130 (14)0.0002 (13)
C9A0.0287 (18)0.0276 (17)0.0293 (16)0.0005 (13)0.0105 (15)0.0023 (14)
C10A0.0325 (17)0.0220 (16)0.0211 (14)0.0004 (13)0.0140 (13)0.0003 (12)
C11A0.0288 (17)0.0233 (16)0.0227 (14)0.0037 (13)0.0088 (13)0.0035 (12)
C12A0.0328 (18)0.0262 (16)0.0248 (15)0.0043 (13)0.0103 (14)0.0026 (13)
C13A0.0355 (18)0.0264 (16)0.0244 (15)0.0026 (14)0.0080 (14)0.0006 (13)
C14A0.0353 (19)0.0229 (16)0.0292 (16)0.0011 (14)0.0091 (14)0.0060 (13)
C15A0.0297 (17)0.0346 (18)0.0327 (17)0.0002 (14)0.0136 (14)0.0018 (14)
C16A0.0317 (18)0.0338 (18)0.0273 (16)0.0007 (14)0.0125 (14)0.0012 (14)
C17A0.0305 (18)0.0331 (18)0.0331 (17)0.0076 (14)0.0066 (15)0.0040 (14)
C18A0.033 (2)0.044 (2)0.049 (2)0.0093 (16)0.0128 (17)0.0002 (17)
C19A0.033 (2)0.048 (2)0.052 (2)0.0054 (17)0.0031 (17)0.0167 (18)
O1B0.0296 (13)0.0254 (12)0.0469 (13)0.0027 (10)0.0014 (11)0.0122 (10)
O2B0.0213 (11)0.0214 (11)0.0332 (11)0.0021 (9)0.0065 (9)0.0002 (9)
O3B0.0282 (12)0.0298 (11)0.0246 (11)0.0002 (9)0.0111 (9)0.0004 (9)
N1B0.0229 (14)0.0231 (13)0.0224 (13)0.0015 (10)0.0063 (11)0.0001 (11)
C1B0.0331 (18)0.0327 (17)0.0275 (16)0.0032 (14)0.0093 (14)0.0018 (14)
C2B0.046 (2)0.0333 (19)0.0343 (18)0.0116 (16)0.0133 (16)0.0031 (15)
C3B0.051 (2)0.0218 (16)0.0402 (19)0.0066 (15)0.0202 (18)0.0035 (14)
C4B0.044 (2)0.0286 (18)0.0336 (17)0.0036 (15)0.0140 (16)0.0052 (14)
C5B0.0305 (17)0.0266 (16)0.0283 (15)0.0001 (13)0.0097 (14)0.0022 (13)
C6B0.0279 (16)0.0240 (15)0.0259 (15)0.0012 (13)0.0162 (14)0.0012 (12)
C7B0.0259 (16)0.0236 (15)0.0265 (14)0.0007 (12)0.0106 (13)0.0010 (12)
C8B0.0221 (15)0.0198 (14)0.0240 (14)0.0008 (12)0.0082 (12)0.0028 (12)
C9B0.0241 (17)0.0229 (15)0.0234 (15)0.0010 (13)0.0054 (13)0.0015 (12)
C10B0.0293 (17)0.0184 (15)0.0274 (16)0.0011 (12)0.0108 (14)0.0003 (12)
C11B0.0243 (16)0.0286 (16)0.0264 (15)0.0049 (13)0.0065 (13)0.0017 (13)
C12B0.0309 (18)0.0240 (16)0.0436 (18)0.0002 (14)0.0079 (15)0.0017 (15)
C13B0.0313 (18)0.0318 (18)0.0410 (18)0.0038 (14)0.0073 (15)0.0033 (15)
C14B0.0268 (17)0.0385 (19)0.0292 (16)0.0054 (14)0.0093 (14)0.0035 (14)
C15B0.0345 (19)0.0250 (17)0.0423 (19)0.0054 (14)0.0068 (16)0.0017 (14)
C16B0.0284 (18)0.0264 (17)0.0390 (18)0.0013 (14)0.0044 (15)0.0001 (14)
C17B0.0262 (19)0.046 (2)0.048 (2)0.0095 (16)0.0036 (16)0.0010 (17)
C18B0.042 (2)0.064 (3)0.049 (2)0.003 (2)0.0039 (19)0.015 (2)
C19B0.030 (2)0.075 (3)0.052 (2)0.0021 (19)0.0094 (18)0.001 (2)
O1C0.0279 (12)0.0360 (12)0.0265 (11)0.0021 (10)0.0067 (10)0.0022 (10)
O2C0.0304 (13)0.0636 (17)0.0315 (12)0.0033 (11)0.0137 (11)0.0027 (12)
O3C0.0324 (13)0.0225 (11)0.0425 (13)0.0014 (10)0.0080 (10)0.0020 (10)
N1C0.0253 (14)0.0199 (13)0.0265 (13)0.0004 (11)0.0073 (11)0.0019 (11)
C1C0.034 (2)0.0359 (19)0.052 (2)0.0075 (15)0.0029 (17)0.0149 (17)
C2C0.041 (2)0.051 (2)0.050 (2)0.0130 (19)0.0073 (19)0.030 (2)
C3C0.066 (3)0.060 (3)0.033 (2)0.024 (2)0.001 (2)0.007 (2)
C4C0.081 (3)0.050 (3)0.0304 (19)0.019 (2)0.010 (2)0.0008 (18)
C5C0.058 (2)0.037 (2)0.0302 (17)0.0042 (18)0.0045 (17)0.0048 (16)
C6C0.0231 (17)0.0384 (19)0.0346 (17)0.0079 (15)0.0027 (14)0.0128 (15)
C7C0.0284 (17)0.0287 (17)0.0369 (18)0.0060 (14)0.0062 (15)0.0034 (14)
C8C0.0273 (17)0.0263 (16)0.0237 (14)0.0009 (13)0.0075 (13)0.0018 (13)
C9C0.0282 (18)0.0218 (15)0.0327 (16)0.0004 (13)0.0113 (15)0.0001 (13)
C10C0.0301 (17)0.0245 (16)0.0197 (14)0.0010 (13)0.0065 (13)0.0017 (12)
C11C0.0293 (17)0.0257 (16)0.0213 (14)0.0001 (13)0.0075 (13)0.0024 (12)
C12C0.0305 (18)0.0385 (18)0.0232 (15)0.0048 (15)0.0062 (14)0.0011 (14)
C13C0.0333 (19)0.043 (2)0.0310 (17)0.0020 (15)0.0143 (15)0.0006 (15)
C14C0.0280 (18)0.0362 (18)0.0319 (16)0.0009 (14)0.0102 (14)0.0081 (15)
C15C0.0295 (19)0.049 (2)0.0278 (17)0.0003 (15)0.0041 (15)0.0025 (15)
C16C0.0303 (18)0.046 (2)0.0222 (15)0.0015 (15)0.0060 (14)0.0033 (14)
C17C0.0293 (19)0.061 (2)0.045 (2)0.0009 (17)0.0173 (16)0.0115 (19)
C18C0.031 (2)0.079 (3)0.050 (2)0.002 (2)0.0071 (18)0.013 (2)
C19C0.047 (3)0.074 (3)0.104 (4)0.005 (2)0.027 (3)0.024 (3)
O1D0.0234 (12)0.0247 (11)0.0301 (11)0.0024 (9)0.0047 (10)0.0021 (9)
O2D0.0227 (12)0.0275 (12)0.0539 (14)0.0036 (10)0.0001 (11)0.0138 (11)
O3D0.0239 (11)0.0306 (11)0.0232 (10)0.0022 (9)0.0094 (9)0.0004 (9)
N1D0.0260 (14)0.0226 (12)0.0191 (12)0.0044 (10)0.0081 (11)0.0030 (10)
C1D0.0361 (19)0.0293 (16)0.0257 (16)0.0029 (14)0.0073 (14)0.0002 (13)
C2D0.0334 (18)0.0336 (18)0.0326 (17)0.0068 (16)0.0010 (15)0.0054 (15)
C3D0.045 (2)0.0316 (19)0.0354 (18)0.0058 (16)0.0047 (17)0.0038 (15)
C4D0.046 (2)0.0292 (18)0.0336 (17)0.0054 (16)0.0038 (16)0.0086 (15)
C5D0.0307 (18)0.0335 (18)0.0307 (17)0.0002 (14)0.0058 (15)0.0004 (14)
C6D0.0277 (17)0.0254 (15)0.0172 (13)0.0012 (13)0.0015 (12)0.0011 (12)
C7D0.0270 (16)0.0216 (14)0.0235 (14)0.0002 (13)0.0059 (12)0.0032 (13)
C8D0.0228 (15)0.0207 (15)0.0237 (14)0.0007 (12)0.0052 (12)0.0001 (12)
C9D0.0269 (17)0.0246 (16)0.0224 (14)0.0048 (13)0.0094 (13)0.0023 (12)
C10D0.0238 (16)0.0158 (14)0.0270 (15)0.0020 (12)0.0071 (13)0.0042 (12)
C11D0.0241 (16)0.0275 (16)0.0218 (14)0.0065 (12)0.0058 (13)0.0021 (12)
C12D0.0292 (17)0.0253 (16)0.0305 (16)0.0035 (13)0.0096 (14)0.0035 (13)
C13D0.0289 (17)0.0243 (16)0.0300 (16)0.0054 (13)0.0070 (14)0.0046 (13)
C14D0.0237 (16)0.0288 (17)0.0282 (16)0.0036 (13)0.0055 (13)0.0009 (13)
C15D0.0261 (17)0.0268 (16)0.0371 (17)0.0033 (13)0.0037 (14)0.0022 (14)
C16D0.0260 (16)0.0227 (15)0.0327 (16)0.0025 (13)0.0065 (13)0.0047 (13)
C17D0.0264 (17)0.0309 (18)0.0406 (18)0.0059 (14)0.0076 (15)0.0027 (14)
C18D0.031 (2)0.049 (2)0.087 (3)0.0058 (17)0.020 (2)0.009 (2)
C19D0.037 (2)0.054 (2)0.0375 (19)0.0167 (18)0.0037 (16)0.0057 (17)
O40.0314 (13)0.0269 (12)0.0232 (11)0.0003 (10)0.0080 (10)0.0011 (10)
O50.0364 (13)0.0217 (11)0.0337 (12)0.0015 (10)0.0189 (11)0.0004 (10)
Cl10.0351 (4)0.0228 (4)0.0262 (4)0.0002 (3)0.0055 (3)0.0006 (3)
Cl20.0337 (4)0.0221 (4)0.0333 (4)0.0015 (3)0.0156 (3)0.0008 (3)
Geometric parameters (Å, º) top
O1A—C9A1.239 (4)O3C—C10C1.252 (4)
O2A—C9A1.291 (4)N1C—C10C1.332 (4)
O2A—HO2A0.949 (19)N1C—C8C1.460 (4)
O3A—C10A1.266 (3)N1C—HN1C0.927 (17)
N1A—C10A1.329 (4)C1C—C6C1.392 (5)
N1A—C8A1.450 (4)C1C—C2C1.413 (5)
N1A—HN1A0.944 (18)C1C—H1C0.9500
C1A—C2A1.379 (5)C2C—C3C1.351 (6)
C1A—C6A1.383 (4)C2C—H2C0.9500
C1A—H1A0.9500C3C—C4C1.361 (6)
C2A—C3A1.376 (5)C3C—H3C0.9500
C2A—H2A0.9500C4C—C5C1.404 (5)
C3A—C4A1.368 (5)C4C—H4C0.9500
C3A—H3A0.9500C5C—C6C1.374 (5)
C4A—C5A1.404 (4)C5C—H5C0.9500
C4A—H4A0.9500C6C—C7C1.524 (4)
C5A—C6A1.378 (5)C7C—C8C1.525 (4)
C5A—H5A0.9500C7C—H7CM0.9900
C6A—C7A1.517 (4)C7C—H7CN0.9900
C7A—C8A1.536 (4)C8C—C9C1.522 (4)
C7A—H7E0.9900C8C—H8C1.0000
C7A—H7F0.9900C10C—C11C1.495 (4)
C8A—C9A1.522 (4)C11C—C12C1.532 (4)
C8A—H8A1.0000C11C—C16C1.537 (4)
C10A—C11A1.502 (4)C11C—H11C1.0000
C11A—C12A1.531 (4)C12C—C13C1.528 (4)
C11A—C16A1.541 (4)C12C—H12M0.9900
C11A—H11A1.0000C12C—H12N0.9900
C12A—C13A1.526 (4)C13C—C14C1.522 (4)
C12A—H12E0.9900C13C—H13M0.9900
C12A—H12F0.9900C13C—H13N0.9900
C13A—C14A1.529 (4)C14C—C15C1.527 (4)
C13A—H13E0.9900C14C—C17C1.542 (4)
C13A—H13F0.9900C14C—H14C1.0000
C14A—C15A1.522 (4)C15C—C16C1.524 (4)
C14A—C17A1.544 (4)C15C—H15M0.9900
C14A—H14A1.0000C15C—H15N0.9900
C15A—C16A1.532 (4)C16C—H16M0.9900
C15A—H15E0.9900C16C—H16N0.9900
C15A—H15F0.9900C17C—C19C1.495 (5)
C16A—H16E0.9900C17C—C18C1.543 (5)
C16A—H16F0.9900C17C—H17C1.0000
C17A—C19A1.535 (5)C18C—H18M0.9800
C17A—C18A1.537 (4)C18C—H18N0.9800
C17A—H17A1.0000C18C—H18P0.9800
C18A—H18E0.9800C19C—H19M0.9800
C18A—H18F0.9800C19C—H19N0.9800
C18A—H18G0.9800C19C—H19P0.9800
C19A—H19E0.9800O1D—C9D1.223 (3)
C19A—H19F0.9800O2D—C9D1.317 (3)
C19A—H19G0.9800O2D—HO2D0.944 (19)
O1B—C9B1.233 (3)O3D—C10D1.265 (3)
O2B—C9B1.297 (3)N1D—C10D1.331 (4)
O2B—HO2B0.948 (19)N1D—C8D1.448 (4)
O3B—C10B1.254 (3)N1D—HN1D0.921 (17)
N1B—C10B1.334 (4)C1D—C2D1.388 (4)
N1B—C8B1.446 (4)C1D—C6D1.392 (4)
N1B—HN1B0.905 (18)C1D—H1D0.9500
C1B—C2B1.378 (4)C2D—C3D1.368 (5)
C1B—C6B1.388 (4)C2D—H2D0.9500
C1B—H1B0.9500C3D—C4D1.389 (5)
C2B—C3B1.391 (5)C3D—H3D0.9500
C2B—H2B0.9500C4D—C5D1.391 (5)
C3B—C4B1.384 (5)C4D—H4D0.9500
C3B—H3B0.9500C5D—C6D1.389 (4)
C4B—C5B1.394 (4)C5D—H5D0.9500
C4B—H4B0.9500C6D—C7D1.514 (4)
C5B—C6B1.387 (4)C7D—C8D1.538 (4)
C5B—H5B0.9500C7D—H7DQ0.9900
C6B—C7B1.516 (4)C7D—H7DR0.9900
C7B—C8B1.537 (4)C8D—C9D1.525 (4)
C7B—H7I0.9900C8D—H8D1.0000
C7B—H7J0.9900C10D—C11D1.501 (4)
C8B—C9B1.525 (4)C11D—C12D1.526 (4)
C8B—H8B1.0000C11D—C16D1.548 (4)
C10B—C11B1.502 (4)C11D—H11D1.0000
C11B—C16B1.523 (4)C12D—C13D1.528 (4)
C11B—C12B1.537 (4)C12D—H12Q0.9900
C11B—H11B1.0000C12D—H12R0.9900
C12B—C13B1.532 (4)C13D—C14D1.528 (4)
C12B—H12I0.9900C13D—H13Q0.9900
C12B—H12J0.9900C13D—H13R0.9900
C13B—C14B1.530 (4)C14D—C15D1.521 (4)
C13B—H13I0.9900C14D—C17D1.538 (4)
C13B—H13J0.9900C14D—H14D1.0000
C14B—C15B1.528 (4)C15D—C16D1.539 (4)
C14B—C17B1.540 (4)C15D—H15Q0.9900
C14B—H14B1.0000C15D—H15R0.9900
C15B—C16B1.532 (4)C16D—H16Q0.9900
C15B—H15I0.9900C16D—H16R0.9900
C15B—H15J0.9900C17D—C19D1.520 (5)
C16B—H16I0.9900C17D—C18D1.535 (5)
C16B—H16J0.9900C17D—H17D1.0000
C17B—C19B1.516 (5)C18D—H18Q0.9800
C17B—C18B1.539 (5)C18D—H18R0.9800
C17B—H17B1.0000C18D—H18S0.9800
C18B—H18I0.9800C19D—H19Q0.9800
C18B—H18J0.9800C19D—H19R0.9800
C18B—H18K0.9800C19D—H19S0.9800
C19B—H19I0.9800O4—HO4A0.960 (18)
C19B—H19J0.9800O4—HO4B0.960 (19)
C19B—H19K0.9800O4—HO4C0.965 (19)
O1C—C9C1.231 (3)O5—HO5A0.960 (18)
O2C—C9C1.308 (4)O5—HO5B0.958 (19)
O2C—HO2C0.909 (18)O5—HO5C0.970 (19)
C9A—O2A—HO2A111 (3)C8C—N1C—HN1C114.5 (19)
C10A—N1A—C8A120.6 (3)C6C—C1C—C2C119.4 (4)
C10A—N1A—HN1A122 (2)C6C—C1C—H1C120.3
C8A—N1A—HN1A117 (2)C2C—C1C—H1C120.3
C2A—C1A—C6A121.0 (3)C3C—C2C—C1C121.7 (4)
C2A—C1A—H1A119.5C3C—C2C—H2C119.1
C6A—C1A—H1A119.5C1C—C2C—H2C119.1
C3A—C2A—C1A119.8 (3)C2C—C3C—C4C119.0 (4)
C3A—C2A—H2A120.1C2C—C3C—H3C120.5
C1A—C2A—H2A120.1C4C—C3C—H3C120.5
C4A—C3A—C2A119.9 (3)C3C—C4C—C5C120.7 (4)
C4A—C3A—H3A120.1C3C—C4C—H4C119.6
C2A—C3A—H3A120.1C5C—C4C—H4C119.6
C3A—C4A—C5A120.5 (3)C6C—C5C—C4C121.0 (4)
C3A—C4A—H4A119.8C6C—C5C—H5C119.5
C5A—C4A—H4A119.8C4C—C5C—H5C119.5
C6A—C5A—C4A119.5 (3)C5C—C6C—C1C118.1 (3)
C6A—C5A—H5A120.2C5C—C6C—C7C124.0 (3)
C4A—C5A—H5A120.2C1C—C6C—C7C117.9 (3)
C5A—C6A—C1A119.2 (3)C8C—C7C—C6C115.0 (3)
C5A—C6A—C7A121.1 (3)C8C—C7C—H7CM108.5
C1A—C6A—C7A119.6 (3)C6C—C7C—H7CM108.5
C6A—C7A—C8A112.2 (2)C8C—C7C—H7CN108.5
C6A—C7A—H7E109.2C6C—C7C—H7CN108.5
C8A—C7A—H7E109.2H7CM—C7C—H7CN107.5
C6A—C7A—H7F109.2N1C—C8C—C9C109.6 (2)
C8A—C7A—H7F109.2N1C—C8C—C7C112.3 (2)
H7E—C7A—H7F107.9C9C—C8C—C7C111.1 (2)
N1A—C8A—C9A111.9 (2)N1C—C8C—H8C107.9
N1A—C8A—C7A112.0 (2)C9C—C8C—H8C107.9
C9A—C8A—C7A108.9 (2)C7C—C8C—H8C107.9
N1A—C8A—H8A107.9O1C—C9C—O2C124.5 (3)
C9A—C8A—H8A107.9O1C—C9C—C8C122.5 (3)
C7A—C8A—H8A107.9O2C—C9C—C8C113.0 (3)
O1A—C9A—O2A124.4 (3)O3C—C10C—N1C119.6 (3)
O1A—C9A—C8A118.7 (3)O3C—C10C—C11C121.7 (3)
O2A—C9A—C8A116.8 (3)N1C—C10C—C11C118.6 (3)
O3A—C10A—N1A118.7 (3)C10C—C11C—C12C116.6 (2)
O3A—C10A—C11A120.7 (3)C10C—C11C—C16C109.5 (2)
N1A—C10A—C11A120.5 (3)C12C—C11C—C16C109.9 (2)
C10A—C11A—C12A115.9 (2)C10C—C11C—H11C106.8
C10A—C11A—C16A108.6 (2)C12C—C11C—H11C106.8
C12A—C11A—C16A109.9 (2)C16C—C11C—H11C106.8
C10A—C11A—H11A107.3C13C—C12C—C11C109.7 (3)
C12A—C11A—H11A107.3C13C—C12C—H12M109.7
C16A—C11A—H11A107.3C11C—C12C—H12M109.7
C13A—C12A—C11A110.8 (2)C13C—C12C—H12N109.7
C13A—C12A—H12E109.5C11C—C12C—H12N109.7
C11A—C12A—H12E109.5H12M—C12C—H12N108.2
C13A—C12A—H12F109.5C14C—C13C—C12C112.8 (2)
C11A—C12A—H12F109.5C14C—C13C—H13M109.0
H12E—C12A—H12F108.1C12C—C13C—H13M109.0
C12A—C13A—C14A112.4 (2)C14C—C13C—H13N109.0
C12A—C13A—H13E109.1C12C—C13C—H13N109.0
C14A—C13A—H13E109.1H13M—C13C—H13N107.8
C12A—C13A—H13F109.1C13C—C14C—C15C110.3 (3)
C14A—C13A—H13F109.1C13C—C14C—C17C113.0 (2)
H13E—C13A—H13F107.9C15C—C14C—C17C114.2 (3)
C15A—C14A—C13A110.1 (2)C13C—C14C—H14C106.2
C15A—C14A—C17A114.7 (3)C15C—C14C—H14C106.2
C13A—C14A—C17A112.7 (2)C17C—C14C—H14C106.2
C15A—C14A—H14A106.2C16C—C15C—C14C112.6 (3)
C13A—C14A—H14A106.2C16C—C15C—H15M109.1
C17A—C14A—H14A106.2C14C—C15C—H15M109.1
C14A—C15A—C16A111.2 (3)C16C—C15C—H15N109.1
C14A—C15A—H15E109.4C14C—C15C—H15N109.1
C16A—C15A—H15E109.4H15M—C15C—H15N107.8
C14A—C15A—H15F109.4C15C—C16C—C11C110.7 (2)
C16A—C15A—H15F109.4C15C—C16C—H16M109.5
H15E—C15A—H15F108.0C11C—C16C—H16M109.5
C15A—C16A—C11A110.5 (2)C15C—C16C—H16N109.5
C15A—C16A—H16E109.5C11C—C16C—H16N109.5
C11A—C16A—H16E109.5H16M—C16C—H16N108.1
C15A—C16A—H16F109.5C19C—C17C—C18C109.8 (3)
C11A—C16A—H16F109.5C19C—C17C—C14C115.1 (3)
H16E—C16A—H16F108.1C18C—C17C—C14C111.1 (3)
C19A—C17A—C18A109.0 (3)C19C—C17C—H17C106.8
C19A—C17A—C14A114.3 (3)C18C—C17C—H17C106.8
C18A—C17A—C14A111.6 (2)C14C—C17C—H17C106.8
C19A—C17A—H17A107.2C17C—C18C—H18M109.5
C18A—C17A—H17A107.2C17C—C18C—H18N109.5
C14A—C17A—H17A107.2H18M—C18C—H18N109.5
C17A—C18A—H18E109.5C17C—C18C—H18P109.5
C17A—C18A—H18F109.5H18M—C18C—H18P109.5
H18E—C18A—H18F109.5H18N—C18C—H18P109.5
C17A—C18A—H18G109.5C17C—C19C—H19M109.5
H18E—C18A—H18G109.5C17C—C19C—H19N109.5
H18F—C18A—H18G109.5H19M—C19C—H19N109.5
C17A—C19A—H19E109.5C17C—C19C—H19P109.5
C17A—C19A—H19F109.5H19M—C19C—H19P109.5
H19E—C19A—H19F109.5H19N—C19C—H19P109.5
C17A—C19A—H19G109.5C9D—O2D—HO2D105 (2)
H19E—C19A—H19G109.5C10D—N1D—C8D120.9 (2)
H19F—C19A—H19G109.5C10D—N1D—HN1D117.6 (19)
C9B—O2B—HO2B115 (3)C8D—N1D—HN1D118.3 (19)
C10B—N1B—C8B122.1 (2)C2D—C1D—C6D120.4 (3)
C10B—N1B—HN1B115 (2)C2D—C1D—H1D119.8
C8B—N1B—HN1B120 (2)C6D—C1D—H1D119.8
C2B—C1B—C6B120.6 (3)C3D—C2D—C1D120.4 (3)
C2B—C1B—H1B119.7C3D—C2D—H2D119.8
C6B—C1B—H1B119.7C1D—C2D—H2D119.8
C1B—C2B—C3B120.5 (3)C2D—C3D—C4D120.2 (3)
C1B—C2B—H2B119.8C2D—C3D—H3D119.9
C3B—C2B—H2B119.8C4D—C3D—H3D119.9
C4B—C3B—C2B119.1 (3)C3D—C4D—C5D119.6 (3)
C4B—C3B—H3B120.4C3D—C4D—H4D120.2
C2B—C3B—H3B120.4C5D—C4D—H4D120.2
C3B—C4B—C5B120.4 (3)C6D—C5D—C4D120.7 (3)
C3B—C4B—H4B119.8C6D—C5D—H5D119.7
C5B—C4B—H4B119.8C4D—C5D—H5D119.7
C6B—C5B—C4B120.1 (3)C5D—C6D—C1D118.8 (3)
C6B—C5B—H5B119.9C5D—C6D—C7D121.2 (3)
C4B—C5B—H5B119.9C1D—C6D—C7D120.0 (3)
C1B—C6B—C5B119.2 (3)C6D—C7D—C8D112.8 (2)
C1B—C6B—C7B119.6 (3)C6D—C7D—H7DQ109.0
C5B—C6B—C7B121.2 (3)C8D—C7D—H7DQ109.0
C6B—C7B—C8B113.3 (2)C6D—C7D—H7DR109.0
C6B—C7B—H7I108.9C8D—C7D—H7DR109.0
C8B—C7B—H7I108.9H7DQ—C7D—H7DR107.8
C6B—C7B—H7J108.9N1D—C8D—C9D109.9 (2)
C8B—C7B—H7J108.9N1D—C8D—C7D111.7 (2)
H7I—C7B—H7J107.7C9D—C8D—C7D109.7 (2)
N1B—C8B—C9B112.2 (2)N1D—C8D—H8D108.5
N1B—C8B—C7B110.6 (2)C9D—C8D—H8D108.5
C9B—C8B—C7B108.4 (2)C7D—C8D—H8D108.5
N1B—C8B—H8B108.5O1D—C9D—O2D124.2 (3)
C9B—C8B—H8B108.5O1D—C9D—C8D123.4 (3)
C7B—C8B—H8B108.5O2D—C9D—C8D112.4 (3)
O1B—C9B—O2B124.2 (3)O3D—C10D—N1D119.3 (3)
O1B—C9B—C8B119.1 (3)O3D—C10D—C11D121.5 (2)
O2B—C9B—C8B116.8 (3)N1D—C10D—C11D119.2 (2)
O3B—C10B—N1B120.1 (3)C10D—C11D—C12D115.3 (2)
O3B—C10B—C11B123.6 (3)C10D—C11D—C16D108.7 (2)
N1B—C10B—C11B116.3 (3)C12D—C11D—C16D110.9 (2)
C10B—C11B—C16B113.6 (3)C10D—C11D—H11D107.2
C10B—C11B—C12B109.9 (2)C12D—C11D—H11D107.2
C16B—C11B—C12B110.6 (2)C16D—C11D—H11D107.2
C10B—C11B—H11B107.5C11D—C12D—C13D109.3 (2)
C16B—C11B—H11B107.5C11D—C12D—H12Q109.8
C12B—C11B—H11B107.5C13D—C12D—H12Q109.8
C13B—C12B—C11B110.3 (3)C11D—C12D—H12R109.8
C13B—C12B—H12I109.6C13D—C12D—H12R109.8
C11B—C12B—H12I109.6H12Q—C12D—H12R108.3
C13B—C12B—H12J109.6C14D—C13D—C12D111.3 (2)
C11B—C12B—H12J109.6C14D—C13D—H13Q109.4
H12I—C12B—H12J108.1C12D—C13D—H13Q109.4
C14B—C13B—C12B112.1 (3)C14D—C13D—H13R109.4
C14B—C13B—H13I109.2C12D—C13D—H13R109.4
C12B—C13B—H13I109.2H13Q—C13D—H13R108.0
C14B—C13B—H13J109.2C15D—C14D—C13D109.3 (2)
C12B—C13B—H13J109.2C15D—C14D—C17D114.1 (3)
H13I—C13B—H13J107.9C13D—C14D—C17D111.7 (2)
C15B—C14B—C13B110.4 (3)C15D—C14D—H14D107.1
C15B—C14B—C17B112.9 (3)C13D—C14D—H14D107.1
C13B—C14B—C17B113.4 (3)C17D—C14D—H14D107.1
C15B—C14B—H14B106.6C14D—C15D—C16D112.0 (2)
C13B—C14B—H14B106.6C14D—C15D—H15Q109.2
C17B—C14B—H14B106.6C16D—C15D—H15Q109.2
C14B—C15B—C16B112.8 (3)C14D—C15D—H15R109.2
C14B—C15B—H15I109.0C16D—C15D—H15R109.2
C16B—C15B—H15I109.0H15Q—C15D—H15R107.9
C14B—C15B—H15J109.0C15D—C16D—C11D110.1 (2)
C16B—C15B—H15J109.0C15D—C16D—H16Q109.6
H15I—C15B—H15J107.8C11D—C16D—H16Q109.6
C11B—C16B—C15B109.6 (3)C15D—C16D—H16R109.6
C11B—C16B—H16I109.7C11D—C16D—H16R109.6
C15B—C16B—H16I109.7H16Q—C16D—H16R108.2
C11B—C16B—H16J109.7C19D—C17D—C18D110.3 (3)
C15B—C16B—H16J109.7C19D—C17D—C14D114.2 (3)
H16I—C16B—H16J108.2C18D—C17D—C14D112.5 (3)
C19B—C17B—C18B109.7 (3)C19D—C17D—H17D106.4
C19B—C17B—C14B111.9 (3)C18D—C17D—H17D106.4
C18B—C17B—C14B113.2 (3)C14D—C17D—H17D106.4
C19B—C17B—H17B107.2C17D—C18D—H18Q109.5
C18B—C17B—H17B107.2C17D—C18D—H18R109.5
C14B—C17B—H17B107.2H18Q—C18D—H18R109.5
C17B—C18B—H18I109.5C17D—C18D—H18S109.5
C17B—C18B—H18J109.5H18Q—C18D—H18S109.5
H18I—C18B—H18J109.5H18R—C18D—H18S109.5
C17B—C18B—H18K109.5C17D—C19D—H19Q109.5
H18I—C18B—H18K109.5C17D—C19D—H19R109.5
H18J—C18B—H18K109.5H19Q—C19D—H19R109.5
C17B—C19B—H19I109.5C17D—C19D—H19S109.5
C17B—C19B—H19J109.5H19Q—C19D—H19S109.5
H19I—C19B—H19J109.5H19R—C19D—H19S109.5
C17B—C19B—H19K109.5HO4A—O4—HO4B120 (4)
H19I—C19B—H19K109.5HO4A—O4—HO4C101 (3)
H19J—C19B—H19K109.5HO4B—O4—HO4C103 (4)
C9C—O2C—HO2C107 (3)HO5A—O5—HO5B106 (4)
C10C—N1C—C8C120.3 (3)HO5A—O5—HO5C115 (3)
C10C—N1C—HN1C121.6 (19)HO5B—O5—HO5C112 (4)
N1A—C8A—C9A—O1A166.8 (3)C17B—C14B—C15B—C16B177.9 (3)
N1A—C8A—C9A—O2A15.3 (4)C10B—C11B—C16B—C15B177.8 (2)
N1A—C10A—C11A—C14A36.5 (6)C12B—C11B—C16B—C15B58.1 (3)
C8A—N1A—C10A—O3A7.5 (4)C14B—C15B—C16B—C11B56.7 (4)
N1B—C8B—C9B—O1B172.5 (3)C15B—C14B—C17B—C19B168.9 (3)
N1B—C8B—C9B—O2B8.8 (3)C13B—C14B—C17B—C19B64.6 (4)
N1B—C10B—C11B—C14B163.5 (4)C15B—C14B—C17B—C18B66.4 (4)
C8B—N1B—C10B—O3B6.6 (4)C13B—C14B—C17B—C18B60.0 (4)
N1C—C8C—C9C—O1C0.8 (4)C6C—C1C—C2C—C3C1.8 (5)
N1C—C8C—C9C—O2C179.9 (3)C1C—C2C—C3C—C4C2.4 (6)
N1C—C10C—C11C—C14C32.0 (7)C2C—C3C—C4C—C5C1.4 (6)
C8C—N1C—C10C—O3C8.0 (4)C3C—C4C—C5C—C6C0.2 (6)
N1D—C8D—C9D—O1D6.7 (4)C4C—C5C—C6C—C1C0.7 (5)
N1D—C8D—C9D—O2D174.3 (2)C4C—C5C—C6C—C7C179.9 (3)
N1D—C10D—C11D—C14D21.8 (6)C2C—C1C—C6C—C5C0.2 (5)
C8D—N1D—C10D—O3D8.9 (4)C2C—C1C—C6C—C7C179.2 (3)
C6A—C1A—C2A—C3A0.5 (6)C5C—C6C—C7C—C8C5.4 (5)
C1A—C2A—C3A—C4A0.2 (6)C1C—C6C—C7C—C8C175.2 (3)
C2A—C3A—C4A—C5A0.4 (6)C10C—N1C—C8C—C9C77.7 (3)
C3A—C4A—C5A—C6A0.9 (6)C10C—N1C—C8C—C7C158.3 (3)
C4A—C5A—C6A—C1A1.1 (5)C6C—C7C—C8C—N1C62.7 (3)
C4A—C5A—C6A—C7A179.7 (3)C6C—C7C—C8C—C9C174.1 (3)
C2A—C1A—C6A—C5A0.9 (5)C7C—C8C—C9C—O1C125.5 (3)
C2A—C1A—C6A—C7A179.9 (3)C7C—C8C—C9C—O2C55.4 (3)
C5A—C6A—C7A—C8A104.6 (4)C8C—N1C—C10C—C11C170.8 (2)
C1A—C6A—C7A—C8A76.2 (4)O3C—C10C—C11C—C12C141.1 (3)
C10A—N1A—C8A—C9A69.0 (3)N1C—C10C—C11C—C12C40.1 (4)
C10A—N1A—C8A—C7A168.3 (2)O3C—C10C—C11C—C16C93.4 (3)
C6A—C7A—C8A—N1A78.9 (3)N1C—C10C—C11C—C16C85.3 (3)
C6A—C7A—C8A—C9A156.8 (3)C10C—C11C—C12C—C13C176.5 (3)
C7A—C8A—C9A—O1A68.8 (4)C16C—C11C—C12C—C13C58.2 (3)
C7A—C8A—C9A—O2A109.1 (3)C11C—C12C—C13C—C14C57.5 (4)
C8A—N1A—C10A—C11A168.4 (2)C12C—C13C—C14C—C15C54.2 (4)
O3A—C10A—C11A—C12A149.4 (3)C12C—C13C—C14C—C17C176.7 (3)
N1A—C10A—C11A—C12A34.8 (4)C13C—C14C—C15C—C16C52.9 (4)
O3A—C10A—C11A—C16A86.3 (3)C17C—C14C—C15C—C16C178.6 (3)
N1A—C10A—C11A—C16A89.5 (3)C14C—C15C—C16C—C11C55.5 (4)
C10A—C11A—C12A—C13A179.7 (2)C10C—C11C—C16C—C15C173.1 (3)
C16A—C11A—C12A—C13A56.1 (3)C12C—C11C—C16C—C15C57.7 (3)
C11A—C12A—C13A—C14A55.9 (3)C13C—C14C—C17C—C19C60.6 (4)
C12A—C13A—C14A—C15A55.4 (3)C15C—C14C—C17C—C19C66.5 (4)
C12A—C13A—C14A—C17A175.2 (3)C13C—C14C—C17C—C18C173.8 (3)
C13A—C14A—C15A—C16A56.2 (3)C15C—C14C—C17C—C18C59.1 (4)
C17A—C14A—C15A—C16A175.5 (2)C6D—C1D—C2D—C3D0.3 (5)
C14A—C15A—C16A—C11A58.1 (3)C1D—C2D—C3D—C4D0.9 (5)
C10A—C11A—C16A—C15A174.7 (2)C2D—C3D—C4D—C5D0.7 (5)
C12A—C11A—C16A—C15A57.5 (3)C3D—C4D—C5D—C6D0.1 (5)
C15A—C14A—C17A—C19A62.0 (4)C4D—C5D—C6D—C1D0.6 (4)
C13A—C14A—C17A—C19A65.0 (4)C4D—C5D—C6D—C7D179.3 (3)
C15A—C14A—C17A—C18A62.4 (3)C2D—C1D—C6D—C5D0.5 (4)
C13A—C14A—C17A—C18A170.6 (3)C2D—C1D—C6D—C7D179.5 (3)
C6B—C1B—C2B—C3B1.2 (5)C5D—C6D—C7D—C8D109.9 (3)
C1B—C2B—C3B—C4B0.9 (5)C1D—C6D—C7D—C8D70.1 (3)
C2B—C3B—C4B—C5B0.4 (5)C10D—N1D—C8D—C9D71.4 (3)
C3B—C4B—C5B—C6B0.1 (5)C10D—N1D—C8D—C7D166.7 (2)
C2B—C1B—C6B—C5B1.0 (4)C6D—C7D—C8D—N1D69.7 (3)
C2B—C1B—C6B—C7B177.1 (3)C6D—C7D—C8D—C9D168.3 (2)
C4B—C5B—C6B—C1B0.4 (4)C7D—C8D—C9D—O1D116.4 (3)
C4B—C5B—C6B—C7B177.6 (3)C7D—C8D—C9D—O2D62.6 (3)
C1B—C6B—C7B—C8B85.9 (3)C8D—N1D—C10D—C11D169.5 (3)
C5B—C6B—C7B—C8B96.1 (3)O3D—C10D—C11D—C12D134.0 (3)
C10B—N1B—C8B—C9B69.4 (3)N1D—C10D—C11D—C12D47.6 (4)
C10B—N1B—C8B—C7B169.4 (2)O3D—C10D—C11D—C16D100.7 (3)
C6B—C7B—C8B—N1B68.8 (3)N1D—C10D—C11D—C16D77.6 (3)
C6B—C7B—C8B—C9B167.9 (2)C10D—C11D—C12D—C13D178.0 (2)
C7B—C8B—C9B—O1B65.1 (3)C16D—C11D—C12D—C13D57.8 (3)
C7B—C8B—C9B—O2B113.6 (3)C11D—C12D—C13D—C14D59.8 (3)
C8B—N1B—C10B—C11B172.7 (3)C12D—C13D—C14D—C15D58.9 (3)
O3B—C10B—C11B—C16B51.4 (4)C12D—C13D—C14D—C17D173.9 (2)
N1B—C10B—C11B—C16B129.3 (3)C13D—C14D—C15D—C16D56.6 (3)
O3B—C10B—C11B—C12B73.1 (4)C17D—C14D—C15D—C16D177.5 (3)
N1B—C10B—C11B—C12B106.2 (3)C14D—C15D—C16D—C11D55.4 (3)
C10B—C11B—C12B—C13B175.5 (3)C10D—C11D—C16D—C15D176.5 (2)
C16B—C11B—C12B—C13B58.3 (3)C12D—C11D—C16D—C15D55.7 (3)
C11B—C12B—C13B—C14B56.0 (3)C15D—C14D—C17D—C19D55.0 (4)
C12B—C13B—C14B—C15B53.4 (3)C13D—C14D—C17D—C19D69.7 (4)
C12B—C13B—C14B—C17B178.8 (3)C15D—C14D—C17D—C18D71.8 (4)
C13B—C14B—C15B—C16B54.0 (4)C13D—C14D—C17D—C18D163.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—HO2A···O1C0.95 (2)1.70 (2)2.643 (3)177 (5)
N1A—HN1A···Cl20.94 (2)2.44 (2)3.348 (3)160 (3)
O2B—HO2B···O1D0.95 (2)1.72 (2)2.653 (3)168 (5)
N1B—HN1B···Cl10.91 (2)2.34 (2)3.237 (2)173 (3)
O2C—HO2C···O1A0.91 (2)1.70 (2)2.609 (3)174 (4)
N1C—HN1C···Cl10.93 (2)2.40 (2)3.300 (3)163 (3)
O2D—HO2D···O1B0.94 (2)1.64 (2)2.569 (3)168 (4)
N1D—HN1D···Cl20.92 (2)2.37 (2)3.262 (2)163 (3)
O4—HO4A···O3Ci0.96 (2)1.58 (2)2.530 (3)172 (4)
O4—HO4B···O3Di0.96 (2)1.51 (2)2.454 (3)166 (6)
O4—HO4C···Cl10.97 (2)2.05 (2)3.008 (2)171 (4)
O5—HO5A···Cl20.96 (2)2.00 (2)2.959 (2)172 (3)
O5—HO5C···O3Aii0.97 (2)1.49 (2)2.459 (3)178 (4)
O5—HO5B···O3Bii0.96 (2)1.57 (2)2.506 (3)165 (5)
Symmetry codes: (i) x, y+1/2, z+1; (ii) x, y1/2, z.

Experimental details

Crystal data
Chemical formulaH3O+·2C19H27NO3·Cl
Mr689.31
Crystal system, space groupMonoclinic, P21
Temperature (K)110
a, b, c (Å)14.0121 (2), 19.6631 (3), 15.3773 (2)
β (°) 110.2998 (8)
V3)3973.62 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.35 × 0.30 × 0.20
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
29123, 15992, 11365
Rint0.071
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.115, 1.03
No. of reflections15992
No. of parameters931
No. of restraints15
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.41, 0.24
Absolute structureFlack (1983), 6258 Friedel pairs
Absolute structure parameter0.01 (4)

Computer programs: Collect (Nonius, 1999), DENZO (Otwinowski & Minor, 1997), DENZO, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Bruno et al., 2002), SHELXL97.

Selected torsion angles (º) top
N1A—C8A—C9A—O1A166.8 (3)N1C—C8C—C9C—O1C0.8 (4)
N1A—C8A—C9A—O2A15.3 (4)N1C—C8C—C9C—O2C179.9 (3)
N1A—C10A—C11A—C14A36.5 (6)N1C—C10C—C11C—C14C32.0 (7)
C8A—N1A—C10A—O3A7.5 (4)C8C—N1C—C10C—O3C8.0 (4)
N1B—C8B—C9B—O1B172.5 (3)N1D—C8D—C9D—O1D6.7 (4)
N1B—C8B—C9B—O2B8.8 (3)N1D—C8D—C9D—O2D174.3 (2)
N1B—C10B—C11B—C14B163.5 (4)N1D—C10D—C11D—C14D21.8 (6)
C8B—N1B—C10B—O3B6.6 (4)C8D—N1D—C10D—O3D8.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—HO2A···O1C0.949 (19)1.70 (2)2.643 (3)177 (5)
N1A—HN1A···Cl20.944 (18)2.44 (2)3.348 (3)160 (3)
O2B—HO2B···O1D0.948 (19)1.72 (2)2.653 (3)168 (5)
N1B—HN1B···Cl10.905 (18)2.337 (19)3.237 (2)173 (3)
O2C—HO2C···O1A0.909 (18)1.703 (19)2.609 (3)174 (4)
N1C—HN1C···Cl10.927 (17)2.402 (19)3.300 (3)163 (3)
O2D—HO2D···O1B0.944 (19)1.64 (2)2.569 (3)168 (4)
N1D—HN1D···Cl20.921 (17)2.369 (19)3.262 (2)163 (3)
O4—HO4A···O3Ci0.960 (18)1.575 (19)2.530 (3)172 (4)
O4—HO4B···O3Di0.960 (19)1.51 (2)2.454 (3)166 (6)
O4—HO4C···Cl10.965 (19)2.05 (2)3.008 (2)171 (4)
O5—HO5A···Cl20.960 (18)2.004 (19)2.959 (2)172 (3)
O5—HO5C···O3Aii0.970 (19)1.490 (19)2.459 (3)178 (4)
O5—HO5B···O3Bii0.958 (19)1.57 (2)2.506 (3)165 (5)
Symmetry codes: (i) x, y+1/2, z+1; (ii) x, y1/2, z.
 

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