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The structures of two brucinium (2,3-dimeth­oxy-10-oxostrychnidinium) salts of the α-hydr­oxy acids L-malic acid and L-tartaric acid, namely brucinium hydrogen (S)-malate penta­hydrate, C23H27N2O4+·C4H5O5·5H2O, (I), and anhydrous brucinium hydrogen (2R,3R)-tartrate, C23H27N2O4+·C4H5O6,(II), have been determined at 130 K. Compound (I) has two brucinium cations, two hydrogen malate anions and ten water mol­ecules of solvation in the asymmetric unit, and forms an extensively hydrogen-bonded three-dimensional framework structure. In compound (II), the brucinium cations form the common undulating brucine sheet substructures, which accommodate parallel chains of head-to-tail hydrogen-bonded tartrate anion species in the inter­stitial cavities.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106017288/gz3010sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106017288/gz3010Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106017288/gz3010IIsup3.hkl
Contains datablock II

CCDC references: 612475; 612476

Comment top

Although the crystal structures of the strychnine salts of both D-tartaric acid [strychninium hydrogen 2(S),3(S)-tartrate trihydrate] and L-tartaric acid [bis(strychninium) 2(R),3(R)-tartrate hexahydrate] have been reported by Gould et al. (1987), surprisingly no brucinium tartrate salts are known. Although brucine is well known as an agent for the resolution of chiral species from enantiomeric mixtures of many organic molecule types including α-hydroxy acids (Wilen, 1972), it is not considered the usual one for the simple series analogues, which include glyceric, malic and tartaric acids. However, the reported resolution of L-glyceric acid from a racemic mixture of the acid and the structure determination of its brucinium salt by Bialońska et al. (2005) prompted us to attempt similar resolutions with malic and tartaric acids. We subsequently obtained crystals of brucinium hydrogen L-malate pentahydrate, (I), by simple refluxing of brucine with D,L-malic acid in 50% ethanol–water. The resolution of D,L-tartaric acid was not as successful under these conditions, so the reaction with L-tartaric acid was completed in 50% 2-propanol–water. The use of 2-propanol rather than ethanol was also to test the observation of Sada et al. (1998) that this solvent promoted the crystallization of brucinium carboxylates, often with incorporation of 2-propanol molecules of solvation. However, with our preparation the well formed clusters of crystals obtained were found to have no molecules of solvation, giving brucinium hydrogen L-tartrate, (II). The structures of both (I) and (II) are reported here.

The structure determination of (I) confirmed the presence of two independent brucinium cations (A and B) (Fig. 1), two hydrogen L-malate anions (C and D) and ten water molecules of solvation (Fig. 2) in the crystallographic asymmetric unit. In (I) as well as in (II) (Fig. 3), the atom-numbering scheme for the brucine cage follows the original Robinson convention employed for strychnine (Holmes, 1952). In both (I) and (II), this gives the overall Cahn–Ingold–Prelog absolute configuration for the protonated brucinium species as C7(S), C8(S), C12(S), C13(R), C14(R), C16(S), N19(S). In the hydrogen malate anions in (I), the carboxylic acid adjacent to the α-hydroxyl group is preferentially deprotonated on the basis of its decreased pKa compared with the C4 carboxylic acid group (Tapscott, 1982). This is consistent with observations for other hydrogen malates, e.g. ammonium hydrogen (S)-malate (Versichel et al., 1978).

In (I), the isolation of the enantiomeric L-malate salt of (I) represents a facile resolution from D,L-malic acid using brucine, which has not previously been considered among recognized resolving agents for this acid. More commonly, 1-phenylethylamine or cinchonine have been the agents of choice for the resolution of both D– and L-malic acid, while both of these as well as quinine have been used for D-malic acid resolution (McKenzie et al., 1923; Newman, 1981). The structures of three configurational isomers of 1-phenylethylaminium D–, L– and DL-malate have been reported (Turkington et al., 2004). In (I), the crystallographic asymmetric unit comprises two independent brucine cations, together with two hydrogen L-malate anions (having the expected S configuration and being conformationally similar; Table 1) and ten water molecules of hydration, which form an extensively hydrogen-bonded three-dimensional framework structure (Fig. 4 and Table 2). This structure is in many respects [viz. space group (P1), unit-cell dimensions and contents] similar to the structures of both brucinium L-glycerate 4.75 hydrate (Bialońska et al., 2005) and brucinium citrate pentahydrate (Smith et al., 2005). With brucine compounds generally, the brucine species commonly form regular undulating parallel or antiparallel host sheet substructures built from partially overlapping head-to-tail molecular associations (Gould & Walkinshaw, 1984; Dijksma, Gould, Parsons, Taylor & Walkinshaw, 1998; Bialońska & Ciunik, 2004). However, in (I) there is no such directional substructuring, although, as with the L-glycerate and citrate compounds, there is the presence of significant structuring within the guest cavity, including numerous cyclic and extended-chain water–water and water–anion hydrogen-bonding interactions. In addition, in (I), there are brucine N+—H ···O(malate) interactions (four-centred in A and three-centred in B) and malate O—H···O (brucine) host–guest interactions.

The brucine molecules in (II) form the previously described parallel-mode substructures, which in (II) extend along the a direction in the unit cell, with a dimeric repeat of ca 12.27 Å and a chain offset angle α (Smith et al., 2006) of ca 118° (Fig. 5). These values compare with 12.66 Å and 123°, respectively, in the similar parallel-mode brucinium D-glucuronate structure (Dijksma, Gould, Parsons & Walkinshaw, 1998). The inter-sheet cavities accommodate the hydrogen tartrate anion species, which form parallel chain structures through head-to-tail cyclic R22(9) hydrogen-bonding interactions (Table 4). These associations incorporate an intramolecular tartrate O21T(hydroxy)—H···O11T(carboxyl) hydrogen bond (Table 4). The chains are linked peripherally to the brucinium cation substructure through O(hydroxy)—H···O(carbonyl) and N+(brucine)—H···O(carboxyl) interactions, giving a three-dimensional cage structure. The tartrate chains in (II) are similar to the succinate chain substructure found in strychnidinium hydrogen succinate (Maurin et al., 2006). In this analysis, the accepted 2(R),3(R) absolute configuration is confirmed for the L-tartrate residue, which also adopts an extended conformation (Table 3).

Experimental top

Both compounds were synthesized by heating 1 mmol quantities of either D,L-malic acid for (I) or L-tartaric acid for (II) and brucine tetrahydrate in 50 ml of either 50% ethanol–water for (I) or 50% 2-propanol–water for (II) for 10 min under reflux. Compound (I) was obtained as colourless plates (m.p. 493.5–495.8 K), while (II) was obtained as clusters of colourless prisms (m.p. 522.4–523.6 K), after partial room-temperature evaporation of the solvent.

Refinement top

H atoms potentially involved in hydrogen-bonding interactions were generally located by difference methods or, in the case of (I), where the water H atoms could not be located by difference methods, positioned in their probable interactive sites and their positional parameters refined. For (II), both positional and isotropic displacement parameters for the interactive H atoms were refined. However, for (I), because of the low reflection/refined parameter ratio the interactive H atoms were fixed in the final cycle of refinement. Other brucine and hydroxy H atoms in both (I) and (II) were included at calculated positions [C—H(aromatic) = 0.93 Å and C—H(aliphatic) = 0.96–1.00 Å] and treated as riding [Uiso(H) = 1.2Ueq(C)]. In both structures, Friedel pairs were averaged for the data used in the refinements. The absolute configuration determined for the parent strychnine (Peerdeman, 1956) was invoked.

Computing details top

For both compounds, data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) in WinGX (Farrugia, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) in WinGX; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for the two independent brucinium cations (A and B) in the asymmetric unit in (I). Non-H atoms are shown as 40% probability displacement ellipsoids.
[Figure 2] Fig. 2. The molecular configuration and atom-numbering scheme for the two L-malate anions (C and D) and the ten water molecules of solvation in (I). Non-H atoms are shown as 40% probability displacement ellipsoids.
[Figure 3] Fig. 3. The molecular configuration and atom numbering scheme for the brucinium cation and the hydrogen L-tartrate anion in (II). The intramolecular O(hydroxy)—H···O(carboxyl) hydrogen bond in the tartrate anion is shown as a broken line. Non-H atoms are shown as 40% probability displacement ellipsoids.
[Figure 4] Fig. 4. The packing of (I), viewed down the a axial direction, showing hydrogen- bonding interactions as broken lines. Non-interactive H atoms have been omitted. For symmetry codes, see Table 2.
[Figure 5] Fig. 5. A perspective view of the packing of (II), viewed approximately down the b axial direction. Non-interactive H atoms have been omitted. For symmetry codes, see Table 4.
(I) 2,3-dimethoxy-10-oxostrychnidinium hydrogen (S)-malate pentahydrate top
Crystal data top
C23H27N2O4+·C4H5O5·5H2OZ = 2
Mr = 618.63F(000) = 660
Triclinic, P1Dx = 1.438 Mg m3
Hall symbol: P 1Melting point = 493.5–495.8 K
a = 9.2915 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.4337 (9) ÅCell parameters from 2640 reflections
c = 16.9287 (17) Åθ = 2.2–26.5°
α = 76.401 (2)°µ = 0.12 mm1
β = 88.716 (2)°T = 130 K
γ = 82.104 (2)°Plate, colourless
V = 1428.5 (3) Å30.40 × 0.35 × 0.05 mm
Data collection top
Bruker CCD area-detector
diffractometer
4397 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.025
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ϕ and ω scansh = 1110
7141 measured reflectionsk = 911
5034 independent reflectionsl = 2015
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 0.90 w = 1/[σ2(Fo2) + (0.0367P)2 + 0.2077P]
where P = (Fo2 + 2Fc2)/3
5034 reflections(Δ/σ)max = 0.005
772 parametersΔρmax = 0.17 e Å3
3 restraintsΔρmin = 0.18 e Å3
Crystal data top
C23H27N2O4+·C4H5O5·5H2Oγ = 82.104 (2)°
Mr = 618.63V = 1428.5 (3) Å3
Triclinic, P1Z = 2
a = 9.2915 (10) ÅMo Kα radiation
b = 9.4337 (9) ŵ = 0.12 mm1
c = 16.9287 (17) ÅT = 130 K
α = 76.401 (2)°0.40 × 0.35 × 0.05 mm
β = 88.716 (2)°
Data collection top
Bruker CCD area-detector
diffractometer
4397 reflections with I > 2σ(I)
7141 measured reflectionsRint = 0.025
5034 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0363 restraints
wR(F2) = 0.072H-atom parameters constrained
S = 0.90Δρmax = 0.17 e Å3
5034 reflectionsΔρmin = 0.18 e Å3
772 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O2A0.8476 (2)0.2908 (2)0.83173 (14)0.0247 (8)
O3A0.7836 (2)0.4006 (2)0.95635 (14)0.0237 (8)
O24A0.0801 (3)0.9854 (2)0.67172 (14)0.0272 (8)
O25A0.3592 (3)0.8094 (2)0.91036 (14)0.0244 (8)
N9A0.3500 (3)0.6944 (3)0.80624 (16)0.0188 (9)
N19A0.2973 (3)0.5660 (3)0.56171 (17)0.0232 (10)
C1A0.6246 (4)0.4169 (3)0.7601 (2)0.0197 (11)
C2A0.7201 (4)0.3836 (3)0.8250 (2)0.0196 (11)
C3A0.6863 (4)0.4465 (3)0.8927 (2)0.0193 (11)
C4A0.5644 (4)0.5485 (3)0.8917 (2)0.0198 (11)
C5A0.4745 (4)0.5851 (3)0.8234 (2)0.0184 (11)
C6A0.5004 (4)0.5184 (3)0.7596 (2)0.0199 (11)
C7A0.3779 (4)0.5674 (3)0.6980 (2)0.0183 (10)
C8A0.2984 (4)0.7069 (3)0.7220 (2)0.0193 (11)
C10A0.3147 (4)0.8090 (4)0.8418 (2)0.0206 (11)
C11A0.2126 (4)0.9370 (4)0.7934 (2)0.0218 (11)
C12A0.2250 (4)0.9741 (4)0.6999 (2)0.0231 (11)
C13A0.3310 (3)0.8560 (3)0.6725 (2)0.0194 (11)
C14A0.3435 (4)0.8607 (4)0.5808 (2)0.0220 (11)
C15A0.4698 (4)0.7433 (4)0.5718 (2)0.0222 (11)
C16A0.4271 (4)0.5924 (4)0.6084 (2)0.0211 (11)
C17A0.2750 (4)0.4497 (4)0.7040 (2)0.0218 (11)
C18A0.1916 (4)0.5000 (4)0.6241 (2)0.0247 (12)
C20A0.2272 (4)0.7031 (4)0.5030 (2)0.0269 (12)
C21A0.2072 (4)0.8325 (4)0.5431 (2)0.0234 (11)
C22A0.0809 (4)0.9130 (4)0.5437 (2)0.0290 (12)
C23A0.0581 (5)1.0391 (4)0.5857 (2)0.0340 (12)
C25A0.8983 (4)0.2455 (4)0.7602 (2)0.0330 (12)
C26A0.7527 (4)0.4659 (4)1.0239 (2)0.0270 (12)
O2B1.0912 (2)0.5207 (2)0.87425 (14)0.0261 (8)
O3B0.9273 (2)0.6391 (2)0.74872 (14)0.0249 (8)
O24B0.4541 (3)1.2088 (2)1.03226 (14)0.0271 (8)
O25B0.5337 (2)1.0401 (2)0.79287 (14)0.0245 (8)
N9B0.6991 (3)1.0063 (3)0.89500 (16)0.0189 (9)
N19B0.9380 (3)0.9591 (3)1.13831 (18)0.0227 (10)
C1B0.9988 (4)0.7130 (4)0.9437 (2)0.0207 (11)
C2B1.0016 (4)0.6455 (4)0.8793 (2)0.0206 (11)
C3B0.9083 (4)0.7072 (4)0.8118 (2)0.0210 (11)
C4B0.8063 (4)0.8288 (3)0.8113 (2)0.0205 (11)
C5B0.8008 (3)0.8896 (3)0.8793 (2)0.0178 (10)
C6B0.8977 (3)0.8368 (4)0.94318 (19)0.0193 (11)
C7B0.8759 (4)0.9328 (3)1.0034 (2)0.0199 (11)
C8B0.7240 (3)1.0212 (3)0.97923 (19)0.0178 (10)
C10B0.5667 (3)1.0559 (3)0.8603 (2)0.0187 (11)
C11B0.4602 (4)1.1365 (4)0.9085 (2)0.0213 (11)
C12B0.4613 (4)1.0786 (4)1.0016 (2)0.0241 (12)
C13B0.5962 (4)0.9658 (4)1.0290 (2)0.0211 (11)
C14B0.6319 (4)0.9145 (4)1.1206 (2)0.0218 (11)
C15B0.7583 (4)0.7881 (3)1.1311 (2)0.0217 (11)
C16B0.8935 (4)0.8491 (3)1.0930 (2)0.0195 (10)
C17B0.9939 (4)1.0367 (4)0.9960 (2)0.0218 (11)
C18B0.9792 (4)1.0887 (4)1.0747 (2)0.0240 (11)
C20B0.8237 (4)1.0041 (4)1.1960 (2)0.0242 (11)
C21B0.6753 (4)1.0355 (4)1.1577 (2)0.0235 (11)
C22B0.5863 (4)1.1559 (4)1.1592 (2)0.0272 (12)
C23B0.4390 (4)1.1862 (4)1.1189 (2)0.0304 (12)
C26B0.8296 (4)0.6981 (4)0.6816 (2)0.0275 (12)
C25B1.1680 (4)0.4391 (4)0.9463 (2)0.0334 (12)
O11C0.2765 (3)0.4093 (2)0.44599 (15)0.0268 (8)
O12C0.3335 (3)0.1908 (3)0.41621 (17)0.0348 (9)
O21C0.5536 (3)0.4440 (3)0.46374 (16)0.0285 (8)
O41C0.6367 (3)0.0732 (3)0.64366 (16)0.0315 (9)
O42C0.4428 (3)0.2415 (3)0.60560 (14)0.0300 (8)
C1C0.3658 (4)0.3032 (4)0.4352 (2)0.0233 (11)
C2C0.5280 (4)0.3114 (4)0.4430 (2)0.0233 (11)
C3C0.6071 (4)0.1809 (4)0.5037 (2)0.0226 (11)
C4C0.5521 (4)0.1709 (4)0.5886 (2)0.0205 (11)
O11D0.1536 (3)0.9111 (2)0.25474 (15)0.0272 (8)
O12D0.3891 (3)0.8261 (3)0.27593 (15)0.0299 (9)
O21D0.0869 (3)0.6524 (3)0.23655 (14)0.0246 (8)
O41D0.3857 (3)0.6330 (3)0.05758 (15)0.0349 (9)
O42D0.2462 (3)0.8160 (3)0.09672 (14)0.0285 (9)
C1D0.2602 (4)0.8125 (4)0.2623 (2)0.0213 (11)
C2D0.2330 (4)0.6566 (4)0.2580 (2)0.0216 (11)
C3D0.3311 (4)0.5963 (4)0.1971 (2)0.0230 (11)
C4D0.3148 (4)0.6940 (4)0.1130 (2)0.0223 (11)
O1W0.7394 (3)0.3885 (3)0.24813 (19)0.0378 (11)
O2W0.5077 (3)0.9571 (3)0.3818 (2)0.0419 (11)
O3W0.8930 (4)0.1846 (3)0.37631 (19)0.0395 (11)
O4W0.7965 (4)0.9032 (3)0.41634 (19)0.0374 (11)
O5W0.0085 (3)0.4009 (3)0.44955 (18)0.0336 (10)
O6W0.0146 (3)0.4165 (4)0.17855 (19)0.0377 (11)
O7W0.6154 (3)0.6176 (3)0.32035 (15)0.0273 (9)
O8W0.1499 (3)0.1722 (3)0.29358 (18)0.0354 (10)
O9W0.8887 (3)0.6725 (3)0.35537 (17)0.0292 (9)
O10W0.7885 (4)0.4385 (4)0.56979 (19)0.0554 (11)
H1A0.642900.371900.716900.0240*
H4A0.543000.591500.935400.0240*
H8A0.193300.704400.722200.0230*
H12A0.260001.069700.681600.0280*
H13A0.427700.867200.690200.0230*
H14A0.367400.957500.552200.0260*
H16A0.509600.517700.604400.0250*
H19A0.32900.50000.52500.0280*
H22A0.002400.891900.517400.0350*
H27A0.226701.024000.811900.0260*
H28A0.114000.917900.806900.0260*
H29A0.492500.752300.514800.0270*
H30A0.555400.756700.599500.0270*
H31A0.329400.352400.709200.0260*
H32A0.210200.448200.749800.0260*
H330.156800.417300.609300.0300*
H34A0.108900.572700.628200.0300*
H35A0.133500.686700.485400.0320*
H36A0.287700.725200.455400.0320*
H37A0.125701.108200.564400.0410*
H38A0.039801.090500.574800.0410*
H39A0.832500.185700.745400.0500*
H40A0.993200.189600.770400.0500*
H41A0.903200.330700.716600.0500*
H42A0.752100.570501.006500.0400*
H43A0.826000.425801.065300.0400*
H44A0.659400.445401.045500.0400*
H1B1.063900.676000.986900.0250*
H4B0.743500.868700.767300.0250*
H8B0.725801.125000.978900.0210*
H12B0.374001.031701.017800.0290*
H13B0.579100.877301.011800.0250*
H14B0.547100.877201.149200.0260*
H16B0.972800.767501.097500.0230*
H19B1.01900.92101.1710.0270*
H22B0.615001.223601.185600.0330*
H27B0.363201.135900.888700.0260*
H28B0.477801.238300.896800.0260*
H29B0.775900.743601.188400.0260*
H30B0.734400.713101.105000.0260*
H31B1.090000.984200.991700.0260*
H32B0.975601.118900.949100.0260*
H33B1.070301.116001.089100.0290*
H34B0.904401.173001.069300.0290*
H35B0.824700.925801.244900.0290*
H36B0.846401.091301.211500.0290*
H37B0.385801.103801.139300.0370*
H38B0.384501.273201.131700.0370*
H39B0.731400.696500.700200.0410*
H40B0.847300.639900.642000.0410*
H41B0.844500.797700.657400.0410*
H42B1.240600.493700.959000.0500*
H43B1.213900.346300.937800.0500*
H44B1.101200.422300.990500.0500*
H2C0.571500.311400.389700.0280*
H21C0.57400.50200.41600.0340*
H31C0.595400.091100.487600.0270*
H32C0.710000.189300.502900.0270*
H41C0.59100.07200.69300.0380*
H2D0.253400.590800.311800.0260*
H21D0.02100.65900.27600.0300*
H31D0.431400.585300.214900.0280*
H32D0.308400.499600.195700.0280*
H41D0.37700.69300.00800.0420*
H11W0.7040.4630.2710.046*
H12W0.8250.4080.2230.046*
H21W0.4670.9260.3470.050*
H22W0.4551.0350.3940.050*
H31W0.9780.1740.3470.047*
H32W0.8400.2540.3430.047*
H41W0.8270.9920.4030.044*
H42W0.7010.9210.4050.044*
H51W0.0880.4040.4480.041*
H52W0.0200.3320.4270.041*
H61W0.0580.3380.2160.046*
H62W0.0380.4930.1980.046*
H71W0.5390.6880.3050.032*
H72W0.6950.6550.3250.032*
H81W0.1620.0760.2850.042*
H82W0.2110.1880.3270.042*
H91W0.9230.5830.3860.035*
H92W0.8670.7410.3860.035*
H10W0.8700.4260.5400.066*
H13W0.7140.4400.5360.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O2A0.0236 (14)0.0233 (13)0.0244 (14)0.0073 (11)0.0033 (11)0.0059 (11)
O3A0.0252 (14)0.0234 (13)0.0213 (13)0.0037 (10)0.0085 (11)0.0063 (11)
O24A0.0260 (14)0.0300 (14)0.0230 (14)0.0050 (11)0.0067 (11)0.0052 (11)
O25A0.0328 (15)0.0237 (13)0.0168 (13)0.0007 (11)0.0033 (11)0.0071 (11)
N9A0.0214 (16)0.0191 (15)0.0162 (15)0.0011 (12)0.0007 (12)0.0059 (12)
N19A0.0272 (18)0.0243 (16)0.0182 (16)0.0001 (13)0.0027 (13)0.0066 (13)
C1A0.0231 (19)0.0192 (18)0.0176 (18)0.0004 (15)0.0039 (15)0.0081 (15)
C2A0.021 (2)0.0163 (18)0.0196 (19)0.0006 (15)0.0016 (15)0.0015 (15)
C3A0.0208 (19)0.0186 (18)0.0181 (19)0.0065 (15)0.0032 (15)0.0008 (15)
C4A0.026 (2)0.0185 (18)0.0160 (18)0.0036 (15)0.0009 (15)0.0058 (15)
C5A0.0178 (19)0.0199 (18)0.0174 (19)0.0041 (14)0.0020 (14)0.0034 (15)
C6A0.022 (2)0.0206 (18)0.0170 (18)0.0055 (15)0.0017 (15)0.0024 (15)
C7A0.0187 (18)0.0176 (17)0.0189 (18)0.0023 (14)0.0007 (14)0.0048 (14)
C8A0.0174 (18)0.0233 (19)0.0172 (18)0.0030 (14)0.0022 (14)0.0042 (15)
C10A0.0196 (19)0.0233 (19)0.020 (2)0.0062 (15)0.0028 (15)0.0059 (16)
C11A0.022 (2)0.0193 (19)0.024 (2)0.0012 (15)0.0008 (16)0.0071 (16)
C12A0.027 (2)0.0177 (18)0.024 (2)0.0040 (15)0.0029 (16)0.0031 (15)
C13A0.0149 (18)0.0241 (19)0.0208 (19)0.0047 (14)0.0004 (14)0.0071 (15)
C14A0.024 (2)0.0196 (18)0.0215 (19)0.0040 (15)0.0013 (15)0.0023 (15)
C15A0.021 (2)0.033 (2)0.0136 (18)0.0043 (16)0.0001 (15)0.0074 (16)
C16A0.0183 (18)0.0250 (19)0.0207 (19)0.0003 (15)0.0031 (15)0.0081 (16)
C17A0.025 (2)0.0205 (18)0.0208 (19)0.0027 (15)0.0027 (16)0.0070 (15)
C18A0.022 (2)0.026 (2)0.029 (2)0.0056 (15)0.0020 (16)0.0109 (17)
C20A0.029 (2)0.029 (2)0.021 (2)0.0009 (17)0.0109 (16)0.0044 (17)
C21A0.026 (2)0.026 (2)0.0157 (19)0.0021 (16)0.0006 (15)0.0005 (15)
C22A0.033 (2)0.031 (2)0.021 (2)0.0024 (18)0.0089 (17)0.0023 (17)
C23A0.040 (2)0.031 (2)0.027 (2)0.0063 (18)0.0094 (18)0.0041 (18)
C25A0.031 (2)0.037 (2)0.026 (2)0.0112 (17)0.0010 (18)0.0062 (19)
C26A0.030 (2)0.028 (2)0.023 (2)0.0002 (16)0.0060 (17)0.0076 (16)
O2B0.0231 (14)0.0254 (14)0.0275 (15)0.0067 (11)0.0026 (11)0.0074 (12)
O3B0.0232 (14)0.0297 (14)0.0240 (14)0.0000 (11)0.0017 (11)0.0127 (12)
O24B0.0318 (15)0.0266 (14)0.0228 (14)0.0038 (11)0.0031 (11)0.0100 (11)
O25B0.0227 (14)0.0311 (14)0.0184 (13)0.0001 (11)0.0056 (10)0.0047 (11)
N9B0.0184 (16)0.0198 (15)0.0183 (15)0.0019 (12)0.0005 (12)0.0046 (12)
N19B0.0252 (18)0.0222 (16)0.0194 (16)0.0027 (14)0.0061 (14)0.0018 (13)
C1B0.0192 (19)0.0218 (19)0.0181 (19)0.0015 (15)0.0015 (15)0.0007 (15)
C2B0.0191 (19)0.0207 (19)0.0211 (19)0.0042 (15)0.0046 (15)0.0028 (15)
C3B0.0197 (19)0.0202 (19)0.024 (2)0.0061 (15)0.0036 (15)0.0053 (16)
C4B0.0174 (19)0.0259 (19)0.0186 (18)0.0009 (15)0.0037 (15)0.0067 (15)
C5B0.0148 (18)0.0194 (18)0.0187 (18)0.0031 (14)0.0000 (14)0.0031 (15)
C6B0.0201 (19)0.0228 (19)0.0151 (18)0.0051 (15)0.0033 (15)0.0036 (15)
C7B0.0207 (19)0.0204 (18)0.0175 (18)0.0035 (15)0.0011 (15)0.0020 (15)
C8B0.0193 (19)0.0148 (17)0.0195 (18)0.0011 (14)0.0023 (14)0.0050 (15)
C10B0.020 (2)0.0173 (18)0.0178 (19)0.0048 (15)0.0032 (15)0.0006 (15)
C11B0.0158 (19)0.0245 (19)0.024 (2)0.0007 (15)0.0031 (15)0.0071 (16)
C12B0.021 (2)0.026 (2)0.026 (2)0.0029 (16)0.0008 (16)0.0078 (16)
C13B0.025 (2)0.0185 (18)0.022 (2)0.0078 (15)0.0005 (16)0.0064 (15)
C14B0.0218 (19)0.0237 (19)0.0198 (19)0.0058 (15)0.0032 (15)0.0036 (16)
C15B0.028 (2)0.0182 (18)0.0175 (18)0.0030 (15)0.0027 (15)0.0013 (15)
C16B0.0232 (19)0.0152 (17)0.0201 (18)0.0011 (14)0.0055 (15)0.0057 (14)
C17B0.0192 (19)0.0248 (19)0.0197 (19)0.0022 (15)0.0041 (15)0.0021 (15)
C18B0.026 (2)0.0213 (19)0.025 (2)0.0080 (15)0.0035 (16)0.0030 (16)
C20B0.032 (2)0.025 (2)0.0163 (18)0.0016 (16)0.0026 (16)0.0075 (16)
C21B0.032 (2)0.027 (2)0.0130 (18)0.0084 (17)0.0021 (16)0.0053 (16)
C22B0.036 (2)0.028 (2)0.019 (2)0.0029 (18)0.0023 (17)0.0092 (16)
C23B0.033 (2)0.033 (2)0.028 (2)0.0047 (17)0.0001 (17)0.0177 (18)
C26B0.027 (2)0.031 (2)0.027 (2)0.0012 (16)0.0004 (17)0.0135 (18)
C25B0.032 (2)0.028 (2)0.036 (2)0.0112 (17)0.0026 (19)0.0075 (18)
O11C0.0260 (14)0.0265 (14)0.0288 (15)0.0024 (11)0.0058 (11)0.0110 (12)
O12C0.0325 (16)0.0318 (15)0.0463 (17)0.0033 (12)0.0087 (13)0.0211 (13)
O21C0.0348 (16)0.0292 (14)0.0240 (14)0.0109 (12)0.0017 (12)0.0071 (12)
O41C0.0334 (16)0.0359 (15)0.0192 (14)0.0093 (12)0.0003 (12)0.0024 (12)
O42C0.0320 (16)0.0303 (14)0.0223 (14)0.0097 (12)0.0013 (12)0.0036 (12)
C1C0.031 (2)0.026 (2)0.0130 (18)0.0054 (17)0.0025 (15)0.0034 (16)
C2C0.029 (2)0.0259 (19)0.0162 (19)0.0054 (16)0.0018 (15)0.0061 (15)
C3C0.021 (2)0.0233 (19)0.024 (2)0.0001 (15)0.0017 (15)0.0079 (16)
C4C0.024 (2)0.0176 (18)0.0204 (19)0.0043 (16)0.0002 (16)0.0047 (15)
O11D0.0265 (15)0.0252 (14)0.0316 (15)0.0039 (12)0.0067 (12)0.0136 (12)
O12D0.0250 (15)0.0279 (14)0.0394 (16)0.0005 (11)0.0093 (12)0.0137 (12)
O21D0.0248 (14)0.0291 (14)0.0208 (13)0.0058 (11)0.0020 (11)0.0065 (12)
O41D0.0473 (18)0.0325 (15)0.0209 (14)0.0066 (13)0.0050 (13)0.0056 (12)
O42D0.0326 (16)0.0262 (15)0.0216 (14)0.0067 (12)0.0009 (11)0.0014 (11)
C1D0.024 (2)0.025 (2)0.0148 (18)0.0008 (16)0.0024 (15)0.0056 (15)
C2D0.023 (2)0.0235 (19)0.0167 (19)0.0010 (15)0.0045 (15)0.0026 (15)
C3D0.0229 (19)0.0209 (19)0.025 (2)0.0009 (15)0.0045 (15)0.0055 (16)
C4D0.0207 (19)0.028 (2)0.022 (2)0.0064 (16)0.0023 (16)0.0113 (16)
O1W0.0353 (19)0.0369 (17)0.0449 (19)0.0062 (14)0.0004 (15)0.0163 (15)
O2W0.0397 (19)0.0424 (19)0.048 (2)0.0098 (14)0.0162 (15)0.0265 (16)
O3W0.0354 (19)0.0357 (18)0.0457 (19)0.0011 (14)0.0002 (16)0.0081 (15)
O4W0.0357 (19)0.0288 (18)0.0493 (19)0.0016 (15)0.0049 (15)0.0134 (15)
O5W0.0301 (17)0.0332 (17)0.0380 (18)0.0010 (13)0.0005 (13)0.0123 (14)
O6W0.0444 (19)0.0341 (19)0.0378 (18)0.0092 (16)0.0061 (14)0.0120 (16)
O7W0.0277 (16)0.0242 (15)0.0277 (15)0.0016 (13)0.0031 (12)0.0023 (12)
O8W0.0330 (17)0.0284 (16)0.0466 (19)0.0028 (12)0.0128 (14)0.0154 (14)
O9W0.0286 (16)0.0279 (16)0.0278 (16)0.0003 (13)0.0009 (12)0.0022 (14)
O10W0.057 (2)0.075 (2)0.0394 (18)0.0088 (17)0.0037 (16)0.0234 (17)
Geometric parameters (Å, º) top
O2A—C2A1.363 (4)C14A—H14A0.9800
O2A—C25A1.426 (4)C15A—H29A0.9700
O24A—C12A1.420 (5)C15A—H30A0.9700
O24A—C23A1.434 (4)C16A—H16A0.9800
O25A—C10A1.242 (4)C17A—H32A0.9700
O3A—C3A1.372 (4)C17A—H31A0.9700
O3A—C26A1.427 (4)C18A—H34A0.9700
O2B—C25B1.427 (4)C18A—H330.9700
O2B—C2B1.364 (4)C20A—H36A0.9700
O24B—C12B1.435 (4)C20A—H35A0.9700
O24B—C23B1.438 (4)C22A—H22A0.9300
O25B—C10B1.236 (4)C23A—H37A0.9700
O3B—C3B1.367 (4)C23A—H38A0.9700
O3B—C26B1.427 (4)C25A—H40A0.9600
O11C—C1C1.255 (4)C25A—H41A0.9600
O12C—C1C1.253 (5)C25A—H39A0.9600
O21C—C2C1.427 (5)C26A—H44A0.9600
O41C—C4C1.329 (5)C26A—H42A0.9600
O42C—C4C1.204 (5)C26A—H43A0.9600
O21C—H21C0.90C1B—C2B1.384 (5)
O41C—H41C0.93C1B—C6B1.393 (5)
O11D—C1D1.249 (4)C2B—C3B1.410 (5)
O12D—C1D1.254 (5)C3B—C4B1.383 (5)
O21D—C2D1.421 (5)C4B—C5B1.399 (4)
O41D—C4D1.329 (4)C5B—C6B1.377 (4)
O42D—C4D1.210 (5)C6B—C7B1.508 (5)
O21D—H21D0.90C7B—C8B1.548 (5)
O41D—H41D0.89C7B—C16B1.537 (5)
O1W—H12W0.91C7B—C17B1.552 (5)
O1W—H11W0.90C8B—C13B1.520 (5)
N9A—C10A1.356 (5)C10B—C11B1.507 (5)
N9A—C5A1.426 (4)C11B—C12B1.542 (5)
N9A—C8A1.488 (4)C12B—C13B1.532 (5)
N19A—C20A1.509 (5)C13B—C14B1.541 (5)
N19A—C18A1.510 (5)C14B—C15B1.536 (5)
N19A—C16A1.536 (5)C14B—C21B1.528 (5)
O2W—H21W0.84C15B—C16B1.521 (5)
O2W—H22W0.89C17B—C18B1.522 (5)
N19A—H19A0.99C20B—C21B1.499 (5)
N9B—C8B1.492 (4)C21B—C22B1.315 (5)
N9B—C10B1.350 (4)C22B—C23B1.504 (5)
N9B—C5B1.420 (4)C1B—H1B0.9300
N19B—C20B1.512 (5)C4B—H4B0.9300
N19B—C16B1.531 (4)C8B—H8B0.9800
N19B—C18B1.514 (5)O8W—H82W0.86
O3W—H31W0.93O8W—H81W0.94
O3W—H32W0.86C11B—H27B0.9700
N19B—H19B0.92C11B—H28B0.9700
O4W—H42W0.90C12B—H12B0.9800
O4W—H41W0.90C13B—H13B0.9800
O5W—H52W0.85C14B—H14B0.9800
O5W—H51W0.90C15B—H29B0.9700
O6W—H62W0.91C15B—H30B0.9700
O6W—H61W0.91C16B—H16B0.9800
C1A—C2A1.378 (5)C17B—H31B0.9700
C1A—C6A1.393 (5)C17B—H32B0.9700
C2A—C3A1.420 (4)C18B—H34B0.9700
C3A—C4A1.379 (5)C18B—H33B0.9700
C4A—C5A1.389 (5)C20B—H35B0.9700
C5A—C6A1.374 (4)C20B—H36B0.9700
C6A—C7A1.510 (5)C22B—H22B0.9300
C7A—C8A1.554 (4)C23B—H37B0.9700
C7A—C17A1.547 (5)C23B—H38B0.9700
C7A—C16A1.548 (5)C26B—H40B0.9600
C8A—C13A1.524 (4)C26B—H41B0.9600
C10A—C11A1.511 (5)C26B—H39B0.9600
C11A—C12A1.544 (5)C25B—H44B0.9600
C12A—C13A1.532 (5)C25B—H43B0.9600
C13A—C14A1.545 (5)C25B—H42B0.9600
C14A—C21A1.514 (5)C1C—C2C1.530 (5)
C14A—C15A1.530 (5)C2C—C3C1.517 (5)
C15A—C16A1.516 (5)C3C—C4C1.501 (5)
C17A—C18A1.516 (5)C2C—H2C0.9800
C20A—C21A1.519 (5)C3C—H32C0.9700
C21A—C22A1.309 (5)C3C—H31C0.9700
C22A—C23A1.512 (5)O9W—H91W0.90
C1A—H1A0.9300O9W—H92W0.92
C4A—H4A0.9300C1D—C2D1.545 (5)
O7W—H71W0.90C2D—C3D1.519 (5)
O7W—H72W0.87C3D—C4D1.501 (5)
C8A—H8A0.9800C2D—H2D0.9800
C11A—H28A0.9700C3D—H31D0.9700
C11A—H27A0.9700C3D—H32D0.9700
C12A—H12A0.9800O10W—H10W0.91
C13A—H13A0.9800O10W—H13W0.90
C2A—O2A—C25A116.8 (3)C1B—C2B—C3B119.9 (3)
C12A—O24A—C23A115.6 (3)O2B—C2B—C1B125.0 (3)
C3A—O3A—C26A115.9 (2)O3B—C3B—C2B115.4 (3)
C2B—O2B—C25B117.3 (3)C2B—C3B—C4B120.9 (3)
C12B—O24B—C23B115.3 (2)O3B—C3B—C4B123.7 (3)
C3B—O3B—C26B115.5 (3)C3B—C4B—C5B117.7 (3)
C2C—O21C—H21C104N9B—C5B—C6B110.4 (3)
C4C—O41C—H41C106N9B—C5B—C4B127.6 (3)
C2D—O21D—H21D115C4B—C5B—C6B122.0 (3)
C4D—O41D—H41D112C1B—C6B—C5B119.8 (3)
H11W—O1W—H12W109C1B—C6B—C7B129.9 (3)
C8A—N9A—C10A119.5 (3)C5B—C6B—C7B110.3 (3)
C5A—N9A—C8A109.0 (3)C6B—C7B—C16B114.8 (3)
C5A—N9A—C10A126.9 (3)C6B—C7B—C8B102.6 (3)
C16A—N19A—C18A107.2 (3)C6B—C7B—C17B112.1 (3)
C18A—N19A—C20A112.2 (3)C8B—C7B—C16B115.2 (3)
C16A—N19A—C20A113.2 (3)C16B—C7B—C17B101.4 (3)
H21W—O2W—H22W112C8B—C7B—C17B111.2 (3)
C18A—N19A—H19A111N9B—C8B—C7B104.4 (2)
C20A—N19A—H19A102N9B—C8B—C13B106.2 (2)
C16A—N19A—H19A111C7B—C8B—C13B116.8 (3)
C8B—N9B—C10B118.8 (3)O25B—C10B—C11B121.2 (3)
C5B—N9B—C10B127.1 (3)O25B—C10B—N9B123.2 (3)
C5B—N9B—C8B108.8 (2)N9B—C10B—C11B115.5 (3)
C16B—N19B—C20B113.7 (3)C10B—C11B—C12B117.6 (3)
C16B—N19B—C18B107.1 (3)O24B—C12B—C11B104.1 (3)
C18B—N19B—C20B112.8 (3)C11B—C12B—C13B110.3 (3)
H31W—O3W—H32W102O24B—C12B—C13B114.5 (3)
C20B—N19B—H19B104C8B—C13B—C14B112.6 (3)
C16B—N19B—H19B112C8B—C13B—C12B107.9 (3)
C18B—N19B—H19B107C12B—C13B—C14B118.5 (3)
H41W—O4W—H42W105C13B—C14B—C21B113.6 (3)
H51W—O5W—H52W105C13B—C14B—C15B107.1 (3)
H61W—O6W—H62W101C15B—C14B—C21B109.1 (3)
C2A—C1A—C6A119.6 (3)C14B—C15B—C16B108.9 (3)
O2A—C2A—C1A125.5 (3)C7B—C16B—C15B114.9 (3)
C1A—C2A—C3A119.5 (3)N19B—C16B—C15B110.0 (3)
O2A—C2A—C3A115.0 (3)N19B—C16B—C7B105.7 (2)
O3A—C3A—C4A123.9 (3)C7B—C17B—C18B103.4 (3)
O3A—C3A—C2A115.4 (3)N19B—C18B—C17B105.4 (3)
C2A—C3A—C4A120.7 (3)N19B—C20B—C21B111.3 (3)
C3A—C4A—C5A118.0 (3)C20B—C21B—C22B122.2 (3)
C4A—C5A—C6A122.0 (3)C14B—C21B—C22B122.4 (3)
N9A—C5A—C6A110.1 (3)C14B—C21B—C20B115.3 (3)
N9A—C5A—C4A127.9 (3)C21B—C22B—C23B121.2 (3)
C1A—C6A—C5A119.9 (3)O24B—C23B—C22B110.1 (3)
C1A—C6A—C7A129.3 (3)C6B—C1B—H1B120.00
C5A—C6A—C7A110.7 (3)C2B—C1B—H1B120.00
C6A—C7A—C8A102.3 (3)C3B—C4B—H4B121.00
C8A—C7A—C16A114.6 (3)C5B—C4B—H4B121.00
C8A—C7A—C17A111.0 (3)N9B—C8B—H8B110.00
C16A—C7A—C17A102.5 (3)C13B—C8B—H8B110.00
C6A—C7A—C16A114.5 (3)C7B—C8B—H8B110.00
C6A—C7A—C17A112.3 (3)H81W—O8W—H82W115
N9A—C8A—C7A104.5 (3)C10B—C11B—H28B108.00
N9A—C8A—C13A106.2 (3)C12B—C11B—H27B108.00
C7A—C8A—C13A117.4 (3)H27B—C11B—H28B107.00
O25A—C10A—C11A121.3 (3)C12B—C11B—H28B108.00
O25A—C10A—N9A123.2 (3)C10B—C11B—H27B108.00
N9A—C10A—C11A115.6 (3)C13B—C12B—H12B109.00
C10A—C11A—C12A118.1 (3)C11B—C12B—H12B109.00
O24A—C12A—C13A114.0 (3)O24B—C12B—H12B109.00
C11A—C12A—C13A110.5 (3)C12B—C13B—H13B106.00
O24A—C12A—C11A104.3 (3)C14B—C13B—H13B106.00
C8A—C13A—C12A107.2 (3)C8B—C13B—H13B106.00
C12A—C13A—C14A118.8 (3)C21B—C14B—H14B109.00
C8A—C13A—C14A112.2 (3)C15B—C14B—H14B109.00
C13A—C14A—C21A114.1 (3)C13B—C14B—H14B109.00
C13A—C14A—C15A106.6 (3)C14B—C15B—H29B110.00
C15A—C14A—C21A109.7 (3)C16B—C15B—H29B110.00
C14A—C15A—C16A109.0 (3)C16B—C15B—H30B110.00
N19A—C16A—C7A104.9 (3)H29B—C15B—H30B108.00
N19A—C16A—C15A110.4 (3)C14B—C15B—H30B110.00
C7A—C16A—C15A115.2 (3)N19B—C16B—H16B109.00
C7A—C17A—C18A102.9 (3)C7B—C16B—H16B109.00
N19A—C18A—C17A106.1 (3)C15B—C16B—H16B109.00
N19A—C20A—C21A110.4 (3)H31B—C17B—H32B109.00
C14A—C21A—C22A123.4 (3)C7B—C17B—H31B111.00
C14A—C21A—C20A115.0 (3)C18B—C17B—H31B111.00
C20A—C21A—C22A121.6 (3)C7B—C17B—H32B111.00
C21A—C22A—C23A122.3 (4)C18B—C17B—H32B111.00
O24A—C23A—C22A110.4 (3)C17B—C18B—H33B111.00
C6A—C1A—H1A120.00H33B—C18B—H34B109.00
C2A—C1A—H1A120.00N19B—C18B—H34B111.00
C3A—C4A—H4A121.00N19B—C18B—H33B111.00
C5A—C4A—H4A121.00C17B—C18B—H34B111.00
H71W—O7W—H72W112N19B—C20B—H36B109.00
C7A—C8A—H8A109.00N19B—C20B—H35B109.00
N9A—C8A—H8A109.00H35B—C20B—H36B108.00
C13A—C8A—H8A109.00C21B—C20B—H36B109.00
C10A—C11A—H28A108.00C21B—C20B—H35B109.00
H27A—C11A—H28A107.00C23B—C22B—H22B119.00
C12A—C11A—H27A108.00C21B—C22B—H22B119.00
C10A—C11A—H27A108.00C22B—C23B—H38B110.00
C12A—C11A—H28A108.00O24B—C23B—H37B110.00
C11A—C12A—H12A109.00H37B—C23B—H38B108.00
C13A—C12A—H12A109.00O24B—C23B—H38B110.00
O24A—C12A—H12A109.00C22B—C23B—H37B110.00
C12A—C13A—H13A106.00O3B—C26B—H40B109.00
C8A—C13A—H13A106.00O3B—C26B—H39B109.00
C14A—C13A—H13A106.00H39B—C26B—H41B109.00
C13A—C14A—H14A109.00O3B—C26B—H41B109.00
C15A—C14A—H14A109.00H39B—C26B—H40B110.00
C21A—C14A—H14A109.00H40B—C26B—H41B109.00
C16A—C15A—H30A110.00O2B—C25B—H43B109.00
C14A—C15A—H30A110.00H42B—C25B—H44B109.00
C14A—C15A—H29A110.00O2B—C25B—H42B109.00
H29A—C15A—H30A108.00H43B—C25B—H44B110.00
C16A—C15A—H29A110.00H42B—C25B—H43B109.00
C7A—C16A—H16A109.00O2B—C25B—H44B109.00
C15A—C16A—H16A109.00O11C—C1C—C2C118.4 (3)
N19A—C16A—H16A109.00O11C—C1C—O12C125.3 (4)
C18A—C17A—H31A111.00O12C—C1C—C2C116.3 (3)
H31A—C17A—H32A109.00O21C—C2C—C3C109.0 (3)
C7A—C17A—H31A111.00O21C—C2C—C1C112.1 (3)
C18A—C17A—H32A111.00C1C—C2C—C3C113.3 (3)
C7A—C17A—H32A111.00C2C—C3C—C4C112.4 (3)
N19A—C18A—H33110.00O41C—C4C—C3C112.5 (3)
N19A—C18A—H34A111.00O42C—C4C—C3C124.3 (3)
C17A—C18A—H33111.00O41C—C4C—O42C123.2 (3)
C17A—C18A—H34A111.00O21C—C2C—H2C107.00
H33—C18A—H34A109.00C1C—C2C—H2C107.00
C21A—C20A—H36A110.00C3C—C2C—H2C107.00
N19A—C20A—H35A110.00C4C—C3C—H32C109.00
C21A—C20A—H35A110.00H31C—C3C—H32C108.00
H35A—C20A—H36A108.00C2C—C3C—H31C109.00
N19A—C20A—H36A110.00C4C—C3C—H31C109.00
C21A—C22A—H22A119.00C2C—C3C—H32C109.00
C23A—C22A—H22A119.00H91W—O9W—H92W112
O24A—C23A—H38A110.00O11D—C1D—C2D118.2 (3)
H37A—C23A—H38A108.00O12D—C1D—C2D115.7 (3)
C22A—C23A—H38A110.00O11D—C1D—O12D126.1 (4)
C22A—C23A—H37A109.00C1D—C2D—C3D112.2 (3)
O24A—C23A—H37A110.00O21D—C2D—C3D107.7 (3)
O2A—C25A—H41A110.00O21D—C2D—C1D112.3 (3)
H39A—C25A—H41A109.00C2D—C3D—C4D112.5 (3)
H40A—C25A—H41A109.00O41D—C4D—O42D123.0 (3)
H39A—C25A—H40A110.00O41D—C4D—C3D112.8 (3)
O2A—C25A—H40A109.00O42D—C4D—C3D124.2 (3)
O2A—C25A—H39A109.00C3D—C2D—H2D108.00
O3A—C26A—H44A110.00C1D—C2D—H2D108.00
H43A—C26A—H44A109.00O21D—C2D—H2D108.00
H42A—C26A—H44A109.00C2D—C3D—H32D109.00
O3A—C26A—H42A110.00C2D—C3D—H31D109.00
O3A—C26A—H43A110.00H31D—C3D—H32D108.00
H42A—C26A—H43A109.00C4D—C3D—H31D109.00
C2B—C1B—C6B119.4 (3)C4D—C3D—H32D109.00
O2B—C2B—C3B115.1 (3)H10W—O10W—H13W105
C25A—O2A—C2A—C1A11.8 (5)O24A—C12A—C13A—C14A54.7 (4)
C25A—O2A—C2A—C3A169.4 (3)C8A—C13A—C14A—C21A60.1 (4)
C23A—O24A—C12A—C11A171.9 (3)C12A—C13A—C14A—C15A172.8 (3)
C23A—O24A—C12A—C13A67.5 (4)C8A—C13A—C14A—C15A61.1 (4)
C12A—O24A—C23A—C22A88.8 (4)C12A—C13A—C14A—C21A65.9 (4)
C26A—O3A—C3A—C2A178.5 (3)C21A—C14A—C15A—C16A55.3 (3)
C26A—O3A—C3A—C4A0.4 (4)C13A—C14A—C21A—C20A122.0 (3)
C25B—O2B—C2B—C1B12.2 (5)C13A—C14A—C15A—C16A68.7 (3)
C25B—O2B—C2B—C3B168.8 (3)C15A—C14A—C21A—C20A2.5 (4)
C23B—O24B—C12B—C11B174.1 (3)C13A—C14A—C21A—C22A58.6 (5)
C23B—O24B—C12B—C13B65.4 (4)C15A—C14A—C21A—C22A178.1 (3)
C12B—O24B—C23B—C22B90.2 (4)C14A—C15A—C16A—C7A55.5 (4)
C26B—O3B—C3B—C2B177.9 (3)C14A—C15A—C16A—N19A63.0 (3)
C26B—O3B—C3B—C4B2.5 (5)C7A—C17A—C18A—N19A34.7 (3)
C5A—N9A—C8A—C13A110.4 (3)N19A—C20A—C21A—C22A127.1 (4)
C10A—N9A—C5A—C4A18.1 (6)N19A—C20A—C21A—C14A53.5 (4)
C5A—N9A—C8A—C7A14.4 (3)C14A—C21A—C22A—C23A2.7 (5)
C10A—N9A—C5A—C6A159.9 (3)C20A—C21A—C22A—C23A178.0 (3)
C8A—N9A—C5A—C4A173.4 (3)C21A—C22A—C23A—O24A64.7 (5)
C8A—N9A—C5A—C6A4.7 (4)C2B—C1B—C6B—C5B0.8 (5)
C10A—N9A—C8A—C13A47.0 (4)C6B—C1B—C2B—O2B177.3 (3)
C8A—N9A—C10A—O25A176.6 (3)C2B—C1B—C6B—C7B177.5 (3)
C10A—N9A—C8A—C7A171.8 (3)C6B—C1B—C2B—C3B3.7 (5)
C5A—N9A—C10A—O25A23.6 (6)C1B—C2B—C3B—O3B175.0 (3)
C5A—N9A—C10A—C11A158.1 (3)O2B—C2B—C3B—O3B4.1 (5)
C8A—N9A—C10A—C11A5.2 (5)O2B—C2B—C3B—C4B176.2 (3)
C18A—N19A—C20A—C21A76.1 (4)C1B—C2B—C3B—C4B4.6 (6)
C16A—N19A—C20A—C21A45.3 (4)C2B—C3B—C4B—C5B1.1 (5)
C20A—N19A—C16A—C15A11.0 (4)O3B—C3B—C4B—C5B178.6 (3)
C20A—N19A—C18A—C17A139.9 (3)C3B—C4B—C5B—C6B3.5 (5)
C20A—N19A—C16A—C7A113.7 (3)C3B—C4B—C5B—N9B174.8 (3)
C18A—N19A—C16A—C15A135.2 (3)N9B—C5B—C6B—C1B174.1 (3)
C16A—N19A—C18A—C17A15.1 (4)C4B—C5B—C6B—C7B174.1 (3)
C18A—N19A—C16A—C7A10.5 (3)C4B—C5B—C6B—C1B4.4 (5)
C10B—N9B—C8B—C7B171.5 (3)N9B—C5B—C6B—C7B7.3 (4)
C10B—N9B—C8B—C13B47.5 (4)C1B—C6B—C7B—C8B165.4 (3)
C5B—N9B—C10B—O25B24.2 (5)C5B—C6B—C7B—C17B103.0 (3)
C8B—N9B—C10B—C11B6.0 (4)C1B—C6B—C7B—C17B75.3 (4)
C10B—N9B—C5B—C6B159.1 (3)C5B—C6B—C7B—C16B142.0 (3)
C5B—N9B—C8B—C13B108.6 (3)C5B—C6B—C7B—C8B16.3 (3)
C8B—N9B—C5B—C6B5.5 (3)C1B—C6B—C7B—C16B39.7 (5)
C8B—N9B—C10B—O25B175.5 (3)C8B—C7B—C17B—C18B81.5 (3)
C5B—N9B—C8B—C7B15.4 (3)C6B—C7B—C17B—C18B164.4 (3)
C5B—N9B—C10B—C11B157.2 (3)C17B—C7B—C16B—N19B33.2 (3)
C8B—N9B—C5B—C4B172.9 (3)C17B—C7B—C16B—C15B154.6 (3)
C10B—N9B—C5B—C4B19.4 (5)C16B—C7B—C8B—N9B143.9 (3)
C16B—N19B—C20B—C21B44.0 (4)C16B—C7B—C17B—C18B41.5 (3)
C18B—N19B—C20B—C21B78.1 (4)C6B—C7B—C8B—N9B18.5 (3)
C20B—N19B—C18B—C17B139.3 (3)C6B—C7B—C16B—N19B154.2 (3)
C18B—N19B—C16B—C7B12.8 (3)C6B—C7B—C16B—C15B84.3 (3)
C20B—N19B—C16B—C15B12.1 (4)C8B—C7B—C16B—N19B87.0 (3)
C16B—N19B—C18B—C17B13.5 (4)C6B—C7B—C8B—C13B98.4 (3)
C20B—N19B—C16B—C7B112.5 (3)C8B—C7B—C16B—C15B34.5 (4)
C18B—N19B—C16B—C15B137.4 (3)C16B—C7B—C8B—C13B27.0 (4)
C2A—C1A—C6A—C7A177.1 (3)C17B—C7B—C8B—C13B141.6 (3)
C2A—C1A—C6A—C5A0.4 (5)C17B—C7B—C8B—N9B101.5 (3)
C6A—C1A—C2A—C3A3.7 (5)N9B—C8B—C13B—C14B156.7 (3)
C6A—C1A—C2A—O2A177.5 (3)N9B—C8B—C13B—C12B70.7 (3)
O2A—C2A—C3A—O3A2.5 (4)C7B—C8B—C13B—C14B40.8 (4)
C1A—C2A—C3A—C4A4.7 (5)C7B—C8B—C13B—C12B173.4 (3)
O2A—C2A—C3A—C4A176.4 (3)O25B—C10B—C11B—C12B143.4 (3)
C1A—C2A—C3A—O3A176.5 (3)N9B—C10B—C11B—C12B38.0 (4)
C2A—C3A—C4A—C5A1.4 (5)C10B—C11B—C12B—C13B12.0 (4)
O3A—C3A—C4A—C5A179.9 (3)C10B—C11B—C12B—O24B135.3 (3)
C3A—C4A—C5A—N9A174.9 (3)C11B—C12B—C13B—C14B169.6 (3)
C3A—C4A—C5A—C6A2.9 (5)C11B—C12B—C13B—C8B40.3 (4)
N9A—C5A—C6A—C7A7.8 (4)O24B—C12B—C13B—C14B52.6 (4)
N9A—C5A—C6A—C1A174.3 (3)O24B—C12B—C13B—C8B76.7 (3)
C4A—C5A—C6A—C7A174.1 (3)C8B—C13B—C14B—C15B60.5 (4)
C4A—C5A—C6A—C1A3.8 (5)C8B—C13B—C14B—C21B60.1 (4)
C5A—C6A—C7A—C16A140.8 (3)C12B—C13B—C14B—C15B172.5 (3)
C1A—C6A—C7A—C16A41.6 (5)C12B—C13B—C14B—C21B67.0 (4)
C5A—C6A—C7A—C17A102.9 (3)C13B—C14B—C15B—C16B67.2 (3)
C1A—C6A—C7A—C17A74.8 (5)C15B—C14B—C21B—C20B1.2 (4)
C5A—C6A—C7A—C8A16.1 (4)C15B—C14B—C21B—C22B178.3 (3)
C1A—C6A—C7A—C8A166.2 (3)C13B—C14B—C21B—C22B62.3 (5)
C17A—C7A—C16A—N19A31.4 (3)C13B—C14B—C21B—C20B120.7 (3)
C8A—C7A—C16A—C15A32.6 (4)C21B—C14B—C15B—C16B56.2 (3)
C16A—C7A—C8A—N9A142.3 (3)C14B—C15B—C16B—N19B63.7 (3)
C17A—C7A—C16A—C15A153.0 (3)C14B—C15B—C16B—C7B55.3 (3)
C6A—C7A—C8A—C13A99.5 (3)C7B—C17B—C18B—N19B34.3 (3)
C6A—C7A—C16A—C15A85.2 (4)N19B—C20B—C21B—C14B51.8 (4)
C17A—C7A—C8A—C13A140.5 (3)N19B—C20B—C21B—C22B131.2 (4)
C8A—C7A—C16A—N19A88.9 (3)C14B—C21B—C22B—C23B4.3 (5)
C6A—C7A—C8A—N9A17.8 (3)C20B—C21B—C22B—C23B178.8 (3)
C16A—C7A—C17A—C18A40.6 (3)C21B—C22B—C23B—O24B66.2 (4)
C8A—C7A—C17A—C18A82.2 (3)O11C—C1C—C2C—O21C1.1 (4)
C16A—C7A—C8A—C13A25.0 (4)O11C—C1C—C2C—C3C125.0 (3)
C6A—C7A—C16A—N19A153.2 (3)O12C—C1C—C2C—O21C179.3 (3)
C17A—C7A—C8A—N9A102.2 (3)O12C—C1C—C2C—C3C56.8 (4)
C6A—C7A—C17A—C18A163.9 (3)C1C—C2C—C3C—C4C62.9 (4)
C7A—C8A—C13A—C12A172.3 (3)O21C—C2C—C3C—C4C62.7 (4)
C7A—C8A—C13A—C14A40.2 (4)C2C—C3C—C4C—O41C169.1 (3)
N9A—C8A—C13A—C14A156.6 (3)C2C—C3C—C4C—O42C11.8 (5)
N9A—C8A—C13A—C12A71.3 (3)O11D—C1D—C2D—O21D6.6 (4)
O25A—C10A—C11A—C12A147.4 (4)O12D—C1D—C2D—O21D175.7 (3)
N9A—C10A—C11A—C12A34.4 (5)O12D—C1D—C2D—C3D54.2 (4)
C10A—C11A—C12A—O24A130.4 (3)O11D—C1D—C2D—C3D128.1 (3)
C10A—C11A—C12A—C13A7.4 (4)C1D—C2D—C3D—C4D57.5 (4)
O24A—C12A—C13A—C8A73.7 (3)O21D—C2D—C3D—C4D66.7 (4)
C11A—C12A—C13A—C14A171.8 (3)C2D—C3D—C4D—O42D9.0 (5)
C11A—C12A—C13A—C8A43.4 (4)C2D—C3D—C4D—O41D171.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N19A—H19A···O11C0.991.862.742 (4)147
N19A—H19A···O21C0.992.363.117 (4)133
N19A—H19A···O42C0.992.593.097 (4)112
N19B—H19B···O11Di0.921.892.759 (4)156
N19B—H19B···O21Di0.922.513.129 (4)124
O21C—H21C···O7W0.901.792.689 (4)180
O21D—H21D···O9Wii0.901.822.719 (4)180
O41C—H41C···O25Biii0.931.732.645 (3)168
O41D—H41D···O25Aiv0.891.752.647 (3)179
O1W—H11W···O7W0.901.932.826 (4)176
O1W—H12W···O6Wv0.911.912.811 (4)171
O2W—H21W···O12D0.841.902.731 (4)171
O2W—H22W···O12Cvi0.891.832.721 (4)175
O3W—H31W···O8Wv0.931.822.743 (5)173
O3W—H32W···O1W0.861.962.805 (4)167
O4W—H41W···O3Wvi0.901.952.845 (4)179
O4W—H42W···O2W0.901.822.712 (5)180
O5W—H51W···O11C0.901.762.659 (4)179
O5W—H52W···O3Wii0.852.062.880 (4)164
O6W—H61W···O8W0.911.902.808 (4)179
O6W—H62W···O21D0.911.892.799 (5)179
O7W—H71W···O12D0.901.762.664 (4)179
O7W—H72W···O9W0.871.922.764 (4)161
O8W—H81W···O11Diii0.941.762.690 (4)168
O8W—H82W···O12C0.861.922.768 (4)169
O9W—H91W···O5Wv0.901.842.738 (4)179
O9W—H92W···O4W0.921.762.653 (4)162
O10W—H10W···O5Wv0.911.922.795 (5)160
O10W—H13W···O21C0.901.942.844 (4)180
C2D—H2D···O11C0.982.503.470 (4)173
C4A—H4A···O25A0.932.452.974 (4)116
C4A—H4A···O41Dvii0.932.583.429 (4)152
C4B—H4B···O25B0.932.462.974 (4)115
C4B—H4B···O41Cvi0.932.603.461 (4)154
C12B—H12B···O42Dvii0.982.583.473 (5)152
C14B—H14B···O12Dvii0.982.563.452 (4)151
C16B—H16B···O21Di0.982.543.120 (4)118
C22B—H22B···O1Wviii0.932.493.408 (5)169
C17A—H31A···O42C0.972.403.106 (5)129
C17B—H31B···O42Di0.972.443.147 (5)130
C3D—H31D···O7W0.972.603.459 (5)148
C17A—H32A···O2Bii0.972.553.471 (4)159
C17B—H32B···O2Avi0.972.463.386 (4)160
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z; (iii) x, y1, z; (iv) x, y, z1; (v) x+1, y, z; (vi) x, y+1, z; (vii) x, y, z+1; (viii) x, y+1, z+1.
(II) 2,3-dimethoxy-10-oxostrychnidinium hydrogen 2(R),3(R)-tartrate top
Crystal data top
C23H27N2O4+·C4H5O6Dx = 1.516 Mg m3
Mr = 544.55Melting point = 522.4–523.6 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ac 2abCell parameters from 4092 reflections
a = 12.2719 (7) Åθ = 2.7–24.0°
b = 13.5151 (8) ŵ = 0.12 mm1
c = 14.3814 (9) ÅT = 130 K
V = 2385.2 (2) Å3Block, colourless
Z = 40.45 × 0.25 × 0.20 mm
F(000) = 1152
Data collection top
Bruker CCD area-detector
diffractometer
2514 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.047
Graphite monochromatorθmax = 27.5°, θmin = 2.1°
ϕ and ω scansh = 1215
15054 measured reflectionsk = 1717
3088 independent reflectionsl = 1815
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 0.91 w = 1/[σ2(Fo2) + (0.0258P)2]
where P = (Fo2 + 2Fc2)/3
3088 reflections(Δ/σ)max = 0.001
368 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C23H27N2O4+·C4H5O6V = 2385.2 (2) Å3
Mr = 544.55Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 12.2719 (7) ŵ = 0.12 mm1
b = 13.5151 (8) ÅT = 130 K
c = 14.3814 (9) Å0.45 × 0.25 × 0.20 mm
Data collection top
Bruker CCD area-detector
diffractometer
2514 reflections with I > 2σ(I)
15054 measured reflectionsRint = 0.047
3088 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.071H atoms treated by a mixture of independent and constrained refinement
S = 0.91Δρmax = 0.24 e Å3
3088 reflectionsΔρmin = 0.22 e Å3
368 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O11T0.20311 (11)0.87831 (10)0.59809 (9)0.0276 (5)
O12T0.32175 (11)0.89712 (11)0.71420 (10)0.0318 (5)
O21T0.35075 (12)0.79171 (11)0.48663 (9)0.0289 (5)
O31T0.41522 (13)0.68629 (10)0.65222 (11)0.0324 (5)
O41T0.57614 (11)0.65356 (10)0.53827 (10)0.0265 (5)
O42T0.62478 (11)0.81248 (10)0.52828 (10)0.0308 (5)
C1T0.29873 (16)0.87445 (14)0.63389 (13)0.0219 (6)
C2T0.38948 (15)0.83956 (14)0.56842 (13)0.0224 (6)
C3T0.46886 (16)0.77278 (14)0.62095 (14)0.0227 (6)
C4T0.56454 (16)0.74840 (15)0.55777 (14)0.0229 (7)
O20.89613 (10)0.60666 (9)0.04769 (9)0.0215 (4)
O30.78668 (10)0.63333 (10)0.19918 (8)0.0216 (4)
O240.18898 (10)0.60648 (9)0.12600 (9)0.0202 (4)
O250.37561 (10)0.65377 (10)0.15612 (9)0.0258 (5)
N90.44948 (12)0.65298 (11)0.01072 (10)0.0162 (5)
N190.52969 (13)0.60273 (11)0.29886 (11)0.0173 (5)
C10.73230 (14)0.61302 (13)0.04751 (13)0.0174 (6)
C20.78570 (14)0.61606 (13)0.03691 (13)0.0167 (6)
C30.72579 (15)0.63132 (13)0.11936 (13)0.0184 (6)
C40.61416 (15)0.64446 (13)0.11761 (12)0.0176 (6)
C50.56242 (14)0.64219 (12)0.03121 (13)0.0160 (6)
C60.62003 (15)0.62646 (13)0.04969 (12)0.0157 (6)
C70.54687 (14)0.63432 (13)0.13353 (12)0.0156 (6)
C80.43118 (14)0.63133 (13)0.08910 (12)0.0153 (5)
C100.36525 (15)0.64392 (13)0.07155 (13)0.0180 (6)
C110.25541 (14)0.62223 (13)0.02726 (13)0.0187 (6)
C120.25361 (15)0.55382 (13)0.05908 (13)0.0181 (6)
C130.36965 (15)0.53302 (13)0.09238 (13)0.0158 (6)
C140.38522 (15)0.47764 (13)0.18471 (13)0.0180 (6)
C150.50837 (15)0.45736 (13)0.19249 (14)0.0179 (6)
C160.56691 (15)0.55471 (13)0.20753 (12)0.0162 (6)
C170.56577 (15)0.73029 (13)0.18874 (12)0.0165 (6)
C180.50801 (16)0.71061 (13)0.27978 (13)0.0201 (6)
C200.43353 (15)0.55163 (14)0.34309 (13)0.0196 (6)
C210.34706 (15)0.53348 (13)0.27118 (13)0.0178 (6)
C220.24538 (16)0.56396 (14)0.28213 (13)0.0209 (6)
C230.16108 (15)0.55040 (15)0.20745 (14)0.0235 (7)
C250.95864 (15)0.59697 (15)0.03671 (14)0.0233 (6)
C260.72647 (16)0.64363 (16)0.28402 (13)0.0253 (7)
H2T0.4309000.8996000.5482000.0270*
H3T0.4968000.8096000.6763000.0270*
H21T0.288 (2)0.760 (2)0.5054 (19)0.077 (10)*
H31T0.398 (2)0.6981 (19)0.710 (2)0.072 (9)*
H41T0.6385 (18)0.6495 (18)0.4954 (17)0.063 (8)*
H10.7710000.6007000.1024000.0210*
H40.5748000.6545000.1721000.0210*
H80.3850000.6846000.1170000.0180*
H11A0.2080000.5922000.0753000.0220*
H11B0.2220000.6862000.0094000.0220*
H120.2169000.4901000.0429000.0220*
H130.4036000.4903000.0435000.0190*
H140.3458000.4130000.1813000.0220*
H15A0.5228000.4122000.2453000.0210*
H15B0.5350000.4255000.1348000.0210*
H160.6470000.5416000.2114000.0190*
H17A0.6445000.7423000.1987000.0200*
H17B0.5337000.7880000.1563000.0200*
H18A0.5379000.7527000.3300000.0240*
H18B0.4289000.7234000.2740000.0240*
H190.5913 (15)0.6029 (13)0.3391 (13)0.020 (5)*
H20A0.4571000.4879000.3704000.0240*
H20B0.4037000.5934000.3936000.0240*
H220.2248000.5946000.3375000.0250*
H23A0.1557000.4794000.1911000.0280*
H23B0.0891000.5722000.2309000.0280*
H25A0.9404000.5342000.0671000.0350*
H25B0.9414000.6520000.0786000.0350*
H25C1.0365000.5981000.0218000.0350*
H26A0.6889000.7076000.2844000.0380*
H26B0.6728000.5902000.2887000.0380*
H26C0.7766000.6401000.3370000.0380*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O11T0.0199 (8)0.0396 (9)0.0234 (8)0.0014 (6)0.0037 (6)0.0041 (7)
O12T0.0333 (9)0.0412 (9)0.0209 (8)0.0037 (7)0.0007 (6)0.0079 (7)
O21T0.0274 (9)0.0432 (9)0.0160 (8)0.0040 (7)0.0003 (6)0.0029 (7)
O31T0.0491 (10)0.0261 (8)0.0219 (9)0.0014 (7)0.0109 (7)0.0036 (7)
O41T0.0319 (9)0.0220 (8)0.0256 (9)0.0049 (6)0.0043 (7)0.0025 (6)
O42T0.0290 (8)0.0268 (8)0.0367 (9)0.0018 (7)0.0044 (7)0.0019 (7)
C1T0.0259 (12)0.0199 (10)0.0200 (11)0.0029 (9)0.0012 (9)0.0005 (8)
C2T0.0235 (11)0.0254 (11)0.0182 (11)0.0021 (9)0.0006 (8)0.0006 (9)
C3T0.0297 (12)0.0211 (10)0.0174 (11)0.0007 (9)0.0005 (9)0.0010 (9)
C4T0.0267 (12)0.0251 (11)0.0168 (11)0.0027 (9)0.0102 (9)0.0010 (9)
O20.0136 (7)0.0325 (8)0.0184 (7)0.0017 (6)0.0017 (5)0.0005 (6)
O30.0157 (7)0.0354 (8)0.0136 (7)0.0031 (6)0.0022 (5)0.0003 (6)
O240.0194 (7)0.0244 (7)0.0169 (7)0.0032 (6)0.0013 (6)0.0012 (6)
O250.0247 (8)0.0367 (8)0.0160 (8)0.0026 (6)0.0017 (6)0.0031 (6)
N90.0153 (8)0.0191 (8)0.0141 (8)0.0015 (7)0.0003 (6)0.0020 (7)
N190.0174 (9)0.0210 (9)0.0134 (9)0.0006 (7)0.0004 (7)0.0020 (7)
C10.0176 (10)0.0167 (10)0.0180 (10)0.0005 (8)0.0037 (8)0.0017 (8)
C20.0149 (10)0.0149 (10)0.0202 (11)0.0004 (7)0.0002 (8)0.0008 (8)
C30.0229 (11)0.0169 (10)0.0153 (10)0.0001 (8)0.0017 (8)0.0015 (8)
C40.0192 (10)0.0205 (10)0.0132 (10)0.0003 (8)0.0011 (8)0.0015 (8)
C50.0169 (10)0.0117 (9)0.0194 (10)0.0011 (8)0.0001 (8)0.0009 (8)
C60.0187 (10)0.0137 (9)0.0148 (10)0.0019 (8)0.0002 (8)0.0003 (8)
C70.0154 (10)0.0158 (9)0.0156 (10)0.0012 (8)0.0022 (7)0.0008 (8)
C80.0182 (10)0.0160 (9)0.0116 (9)0.0040 (8)0.0016 (7)0.0012 (8)
C100.0219 (11)0.0165 (9)0.0157 (10)0.0020 (8)0.0012 (8)0.0024 (8)
C110.0146 (10)0.0208 (10)0.0208 (11)0.0002 (8)0.0039 (8)0.0006 (9)
C120.0170 (10)0.0183 (10)0.0189 (11)0.0020 (8)0.0015 (8)0.0017 (8)
C130.0161 (10)0.0157 (9)0.0157 (10)0.0009 (8)0.0004 (8)0.0020 (8)
C140.0186 (11)0.0145 (9)0.0208 (11)0.0025 (8)0.0006 (8)0.0007 (8)
C150.0192 (11)0.0165 (10)0.0180 (11)0.0006 (8)0.0021 (8)0.0018 (8)
C160.0165 (10)0.0198 (10)0.0124 (10)0.0033 (8)0.0020 (8)0.0009 (8)
C170.0180 (10)0.0171 (10)0.0144 (10)0.0022 (8)0.0016 (8)0.0001 (8)
C180.0257 (11)0.0171 (10)0.0176 (11)0.0002 (8)0.0003 (8)0.0022 (8)
C200.0208 (11)0.0226 (10)0.0155 (11)0.0006 (8)0.0047 (8)0.0019 (8)
C210.0213 (12)0.0163 (10)0.0157 (10)0.0029 (8)0.0022 (8)0.0052 (8)
C220.0253 (12)0.0224 (10)0.0149 (11)0.0025 (9)0.0045 (8)0.0033 (8)
C230.0169 (11)0.0328 (12)0.0209 (11)0.0003 (9)0.0049 (8)0.0028 (9)
C250.0164 (11)0.0314 (11)0.0220 (11)0.0009 (9)0.0042 (8)0.0021 (10)
C260.0240 (12)0.0376 (12)0.0143 (10)0.0035 (9)0.0013 (8)0.0026 (10)
Geometric parameters (Å, º) top
O11T—C1T1.282 (2)C8—C131.529 (2)
O12T—C1T1.228 (2)C10—C111.519 (3)
O21T—C2T1.424 (2)C11—C121.548 (3)
O31T—C3T1.415 (2)C12—C131.528 (3)
O41T—C4T1.320 (2)C13—C141.536 (3)
O42T—C4T1.215 (2)C14—C211.528 (3)
O21T—H21T0.92 (3)C14—C151.540 (3)
O31T—H31T0.87 (3)C15—C161.515 (3)
O41T—H41T0.98 (2)C17—C181.512 (3)
O2—C21.370 (2)C20—C211.502 (3)
O2—C251.442 (2)C21—C221.323 (3)
O24—C121.436 (2)C22—C231.502 (3)
O24—C231.437 (2)C1—H10.9300
O25—C101.230 (2)C4—H40.9300
O3—C261.433 (2)C8—H81.0002
O3—C31.370 (2)C11—H11A0.9902
N9—C51.424 (2)C11—H11B0.9907
N9—C81.482 (2)C12—H120.9994
N9—C101.360 (2)C13—H131.0005
N19—C201.508 (2)C14—H140.9998
N19—C161.535 (2)C15—H15A0.9903
N19—C181.507 (2)C15—H15B0.9902
N19—H190.952 (19)C16—H161.0002
C1T—C2T1.533 (3)C17—H17A0.9901
C2T—C3T1.528 (3)C17—H17B0.9904
C3T—C4T1.521 (3)C18—H18A0.9898
C2T—H2T1.0007C18—H18B0.9896
C3T—H3T0.9994C20—H20A0.9898
C1—C61.390 (3)C20—H20B0.9901
C1—C21.380 (3)C22—H220.9300
C2—C31.410 (3)C23—H23A0.9902
C3—C41.382 (3)C23—H23B0.9904
C4—C51.396 (3)C25—H25A0.9802
C5—C61.378 (3)C25—H25B0.9802
C6—C71.507 (2)C25—H25C0.9794
C7—C161.533 (2)C26—H26A0.9798
C7—C171.538 (2)C26—H26B0.9797
C7—C81.557 (2)C26—H26C0.9804
C2T—O21T—H21T104.4 (17)C7—C16—C15115.75 (15)
C3T—O31T—H31T105.3 (17)C7—C17—C18103.17 (14)
C4T—O41T—H41T105.7 (14)N19—C18—C17104.18 (14)
C2—O2—C25116.07 (14)N19—C20—C21109.71 (15)
C12—O24—C23114.62 (13)C14—C21—C22122.65 (17)
C3—O3—C26115.73 (14)C14—C21—C20115.12 (15)
C5—N9—C8109.12 (14)C20—C21—C22122.23 (17)
C5—N9—C10126.68 (15)C21—C22—C23121.75 (17)
C8—N9—C10119.35 (15)O24—C23—C22110.76 (15)
C18—N19—C20112.44 (14)C2—C1—H1120.48
C16—N19—C20113.59 (14)C6—C1—H1120.40
C16—N19—C18107.81 (14)C3—C4—H4121.16
C20—N19—H19111.5 (11)C5—C4—H4121.16
C18—N19—H19104.4 (11)N9—C8—H8109.41
C16—N19—H19106.6 (11)C7—C8—H8109.47
O12T—C1T—C2T119.17 (17)C13—C8—H8109.47
O11T—C1T—C2T115.51 (16)C10—C11—H11A107.93
O11T—C1T—O12T125.31 (18)C10—C11—H11B107.91
O21T—C2T—C3T110.67 (15)C12—C11—H11A107.84
C1T—C2T—C3T109.95 (15)C12—C11—H11B107.90
O21T—C2T—C1T113.87 (15)H11A—C11—H11B107.18
O31T—C3T—C2T110.40 (16)O24—C12—H12109.52
C2T—C3T—C4T108.96 (16)C11—C12—H12109.53
O31T—C3T—C4T111.72 (16)C13—C12—H12109.54
O41T—C4T—C3T114.88 (17)C8—C13—H13105.91
O41T—C4T—O42T123.53 (18)C12—C13—H13105.90
O42T—C4T—C3T121.59 (18)C14—C13—H13105.92
C3T—C2T—H2T107.39C13—C14—H14108.85
C1T—C2T—H2T107.34C15—C14—H14108.84
O21T—C2T—H2T107.32C21—C14—H14108.85
C4T—C3T—H3T108.59C14—C15—H15A109.93
C2T—C3T—H3T108.57C14—C15—H15B109.90
O31T—C3T—H3T108.53C16—C15—H15A109.94
C2—C1—C6119.11 (17)C16—C15—H15B109.93
O2—C2—C1124.50 (16)H15A—C15—H15B108.39
C1—C2—C3119.76 (16)N19—C16—H16108.65
O2—C2—C3115.73 (16)C7—C16—H16108.70
C2—C3—C4121.36 (17)C15—C16—H16108.67
O3—C3—C4123.61 (16)C7—C17—H17A111.10
O3—C3—C2115.03 (16)C7—C17—H17B111.16
C3—C4—C5117.68 (16)C18—C17—H17A111.16
N9—C5—C4128.65 (16)C18—C17—H17B111.10
N9—C5—C6109.90 (16)H17A—C17—H17B109.08
C4—C5—C6121.44 (16)N19—C18—H18A110.96
C5—C6—C7111.04 (16)N19—C18—H18B110.94
C1—C6—C5120.64 (17)C17—C18—H18A110.91
C1—C6—C7128.15 (16)C17—C18—H18B110.88
C6—C7—C8102.30 (14)H18A—C18—H18B108.93
C6—C7—C16114.22 (15)N19—C20—H20A109.71
C6—C7—C17112.49 (14)N19—C20—H20B109.73
C16—C7—C17102.08 (14)C21—C20—H20A109.73
C8—C7—C17111.78 (14)C21—C20—H20B109.70
C8—C7—C16114.38 (14)H20A—C20—H20B108.24
C7—C8—C13117.39 (15)C21—C22—H22119.11
N9—C8—C13106.04 (14)C23—C22—H22119.15
N9—C8—C7104.72 (13)O24—C23—H23A109.48
O25—C10—N9123.22 (17)O24—C23—H23B109.47
O25—C10—C11121.81 (16)C22—C23—H23A109.50
N9—C10—C11114.97 (16)C22—C23—H23B109.54
C10—C11—C12117.65 (15)H23A—C23—H23B108.04
C11—C12—C13110.35 (15)O2—C25—H25A109.42
O24—C12—C11104.44 (14)O2—C25—H25B109.49
O24—C12—C13113.31 (15)O2—C25—H25C109.47
C8—C13—C12106.90 (14)H25A—C25—H25B109.47
C8—C13—C14112.87 (15)H25A—C25—H25C109.51
C12—C13—C14118.45 (15)H25B—C25—H25C109.47
C15—C14—C21109.24 (15)O3—C26—H26A109.45
C13—C14—C15105.76 (15)O3—C26—H26B109.48
C13—C14—C21115.13 (15)O3—C26—H26C109.47
C14—C15—C16108.74 (14)H26A—C26—H26B109.49
N19—C16—C7104.45 (14)H26A—C26—H26C109.50
N19—C16—C15110.39 (14)H26B—C26—H26C109.43
C25—O2—C2—C3176.42 (15)N9—C5—C6—C74.8 (2)
C25—O2—C2—C12.5 (2)C4—C5—C6—C10.5 (3)
C12—O24—C23—C2290.78 (18)C5—C6—C7—C17106.56 (17)
C23—O24—C12—C1369.28 (18)C1—C6—C7—C8171.21 (18)
C23—O24—C12—C11170.58 (14)C5—C6—C7—C16137.68 (16)
C26—O3—C3—C44.0 (2)C5—C6—C7—C813.53 (19)
C26—O3—C3—C2176.89 (16)C1—C6—C7—C1768.7 (2)
C5—N9—C10—C11158.84 (16)C1—C6—C7—C1647.1 (2)
C10—N9—C5—C6161.74 (17)C17—C7—C16—N1931.70 (17)
C8—N9—C5—C66.89 (19)C6—C7—C8—C13100.60 (17)
C8—N9—C10—O25174.74 (16)C6—C7—C16—C1585.03 (19)
C5—N9—C8—C13109.79 (15)C16—C7—C8—C1323.4 (2)
C5—N9—C10—O2522.2 (3)C17—C7—C8—C13138.81 (16)
C10—N9—C5—C417.3 (3)C16—C7—C17—C1842.96 (17)
C8—N9—C5—C4172.12 (17)C6—C7—C8—N916.64 (17)
C8—N9—C10—C116.3 (2)C8—C7—C16—C1532.4 (2)
C10—N9—C8—C1347.2 (2)C8—C7—C16—N1989.21 (17)
C5—N9—C8—C714.99 (17)C8—C7—C17—C1879.73 (17)
C10—N9—C8—C7171.97 (15)C6—C7—C17—C18165.83 (15)
C18—N19—C20—C2175.30 (18)C17—C7—C8—N9103.94 (16)
C20—N19—C16—C7115.98 (15)C6—C7—C16—N19153.38 (14)
C16—N19—C20—C2147.48 (19)C16—C7—C8—N9140.69 (14)
C20—N19—C16—C159.1 (2)C17—C7—C16—C15153.28 (15)
C18—N19—C16—C15134.37 (15)N9—C8—C13—C1272.35 (17)
C16—N19—C18—C1717.37 (18)C7—C8—C13—C1439.2 (2)
C20—N19—C18—C17143.35 (15)C7—C8—C13—C12171.12 (15)
C18—N19—C16—C79.31 (18)N9—C8—C13—C14155.71 (14)
O11T—C1T—C2T—O21T16.1 (2)N9—C10—C11—C1236.3 (2)
O12T—C1T—C2T—C3T39.8 (2)O25—C10—C11—C12144.71 (17)
O12T—C1T—C2T—O21T164.62 (17)C10—C11—C12—O24130.72 (16)
O11T—C1T—C2T—C3T140.97 (17)C10—C11—C12—C138.6 (2)
C1T—C2T—C3T—C4T173.82 (15)O24—C12—C13—C1455.5 (2)
O21T—C2T—C3T—O31T63.5 (2)C11—C12—C13—C14172.19 (15)
O21T—C2T—C3T—C4T59.5 (2)C11—C12—C13—C843.40 (19)
C1T—C2T—C3T—O31T63.1 (2)O24—C12—C13—C873.32 (18)
O31T—C3T—C4T—O41T4.4 (2)C8—C13—C14—C1560.75 (18)
O31T—C3T—C4T—O42T175.57 (18)C8—C13—C14—C2159.9 (2)
C2T—C3T—C4T—O41T117.85 (18)C12—C13—C14—C2166.0 (2)
C2T—C3T—C4T—O42T62.2 (2)C12—C13—C14—C15173.29 (15)
C6—C1—C2—C30.9 (3)C13—C14—C21—C2258.8 (2)
C2—C1—C6—C7174.57 (17)C13—C14—C21—C20121.08 (17)
C6—C1—C2—O2178.08 (16)C21—C14—C15—C1655.56 (19)
C2—C1—C6—C50.3 (3)C15—C14—C21—C22177.55 (17)
C1—C2—C3—O3179.83 (19)C15—C14—C21—C202.3 (2)
O2—C2—C3—O30.8 (2)C13—C14—C15—C1668.90 (18)
C1—C2—C3—C40.7 (3)C14—C15—C16—N1961.97 (19)
O2—C2—C3—C4178.32 (16)C14—C15—C16—C756.4 (2)
C2—C3—C4—C50.0 (3)C7—C17—C18—N1937.31 (17)
O3—C3—C4—C5179.01 (16)N19—C20—C21—C22125.78 (19)
C3—C4—C5—C60.6 (3)N19—C20—C21—C1454.1 (2)
C3—C4—C5—N9179.53 (16)C20—C21—C22—C23176.52 (17)
C4—C5—C6—C7176.13 (16)C14—C21—C22—C233.3 (3)
N9—C5—C6—C1179.57 (15)C21—C22—C23—O2464.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N19—H19···O11Ti0.952 (19)1.662 (19)2.606 (2)170.4 (17)
O21T—H21T···O11T0.92 (3)2.33 (3)2.687 (2)102.8 (19)
O21T—H21T···O42Tii0.92 (3)2.28 (3)3.118 (2)151 (2)
O31T—H31T···O25iii0.87 (3)2.04 (3)2.833 (2)152 (2)
O41T—H41T···O11Ti0.98 (2)1.61 (2)2.5415 (19)157 (2)
C4—H4···O250.932.462.982 (2)116
C15—H15A···O3iv0.992.553.202 (2)124
C16—H16···O12Ti1.002.543.387 (2)143
C20—H20A···O2iv0.992.503.378 (2)147
C23—H23A···O31Tv0.992.473.426 (2)163
C25—H25A···O41Tvi0.982.583.413 (2)143
C25—H25C···O24vii0.982.403.107 (2)129
C26—H26C···O21Tviii0.982.513.403 (2)151
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x1/2, y+3/2, z+1; (iii) x, y, z+1; (iv) x+3/2, y+1, z+1/2; (v) x+1/2, y+1, z1/2; (vi) x+3/2, y+1, z1/2; (vii) x+1, y, z; (viii) x+1/2, y+3/2, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC23H27N2O4+·C4H5O5·5H2OC23H27N2O4+·C4H5O6
Mr618.63544.55
Crystal system, space groupTriclinic, P1Orthorhombic, P212121
Temperature (K)130130
a, b, c (Å)9.2915 (10), 9.4337 (9), 16.9287 (17)12.2719 (7), 13.5151 (8), 14.3814 (9)
α, β, γ (°)76.401 (2), 88.716 (2), 82.104 (2)90, 90, 90
V3)1428.5 (3)2385.2 (2)
Z24
Radiation typeMo KαMo Kα
µ (mm1)0.120.12
Crystal size (mm)0.40 × 0.35 × 0.050.45 × 0.25 × 0.20
Data collection
DiffractometerBruker CCD area-detector
diffractometer
Bruker CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7141, 5034, 4397 15054, 3088, 2514
Rint0.0250.047
(sin θ/λ)max1)0.5950.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.072, 0.90 0.040, 0.071, 0.91
No. of reflections50343088
No. of parameters772368
No. of restraints30
H-atom treatmentH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.180.24, 0.22

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997) in WinGX (Farrugia, 1999), SHELXL97 (Sheldrick, 1997) in WinGX, PLATON (Spek, 2003), PLATON.

Selected torsion angles (º) for (I) top
O11C—C1C—C2C—O21C1.1 (4)O11D—C1D—C2D—O21D6.6 (4)
O11C—C1C—C2C—C3C125.0 (3)O12D—C1D—C2D—O21D175.7 (3)
O12C—C1C—C2C—O21C179.3 (3)O12D—C1D—C2D—C3D54.2 (4)
O12C—C1C—C2C—C3C56.8 (4)O11D—C1D—C2D—C3D128.1 (3)
C1C—C2C—C3C—C4C62.9 (4)C1D—C2D—C3D—C4D57.5 (4)
O21C—C2C—C3C—C4C62.7 (4)O21D—C2D—C3D—C4D66.7 (4)
C2C—C3C—C4C—O41C169.1 (3)C2D—C3D—C4D—O42D9.0 (5)
C2C—C3C—C4C—O42C11.8 (5)C2D—C3D—C4D—O41D171.8 (3)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N19A—H19A···O11C0.991.862.742 (4)147
N19A—H19A···O21C0.992.363.117 (4)133
N19A—H19A···O42C0.992.593.097 (4)112
N19B—H19B···O11Di0.921.892.759 (4)156
N19B—H19B···O21Di0.922.513.129 (4)124
O21C—H21C···O7W0.901.792.689 (4)180
O21D—H21D···O9Wii0.901.822.719 (4)180
O41C—H41C···O25Biii0.931.732.645 (3)168
O41D—H41D···O25Aiv0.891.752.647 (3)179
O1W—H11W···O7W0.901.932.826 (4)176
O1W—H12W···O6Wv0.911.912.811 (4)171
O2W—H21W···O12D0.841.902.731 (4)171
O2W—H22W···O12Cvi0.891.832.721 (4)175
O3W—H31W···O8Wv0.931.822.743 (5)173
O3W—H32W···O1W0.861.962.805 (4)167
O4W—H41W···O3Wvi0.901.952.845 (4)179
O4W—H42W···O2W0.901.822.712 (5)180
O5W—H51W···O11C0.901.762.659 (4)179
O5W—H52W···O3Wii0.852.062.880 (4)164
O6W—H61W···O8W0.911.902.808 (4)179
O6W—H62W···O21D0.911.892.799 (5)179
O7W—H71W···O12D0.901.762.664 (4)179
O7W—H72W···O9W0.871.922.764 (4)161
O8W—H81W···O11Diii0.941.762.690 (4)168
O8W—H82W···O12C0.861.922.768 (4)169
O9W—H91W···O5Wv0.901.842.738 (4)179
O9W—H92W···O4W0.921.762.653 (4)162
O10W—H10W···O5Wv0.911.922.795 (5)160
O10W—H13W···O21C0.901.942.844 (4)180
C3D—H31D···O7W0.972.603.459 (5)148
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z; (iii) x, y1, z; (iv) x, y, z1; (v) x+1, y, z; (vi) x, y+1, z.
Selected torsion angles (º) for (II) top
O11T—C1T—C2T—O21T16.1 (2)O21T—C2T—C3T—C4T59.5 (2)
O12T—C1T—C2T—C3T39.8 (2)C1T—C2T—C3T—O31T63.1 (2)
O12T—C1T—C2T—O21T164.62 (17)O31T—C3T—C4T—O41T4.4 (2)
O11T—C1T—C2T—C3T140.97 (17)O31T—C3T—C4T—O42T175.57 (18)
C1T—C2T—C3T—C4T173.82 (15)C2T—C3T—C4T—O41T117.85 (18)
O21T—C2T—C3T—O31T63.5 (2)C2T—C3T—C4T—O42T62.2 (2)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N19—H19···O11Ti0.952 (19)1.662 (19)2.606 (2)170.4 (17)
O21T—H21T···O11T0.92 (3)2.33 (3)2.687 (2)102.8 (19)
O21T—H21T···O42Tii0.92 (3)2.28 (3)3.118 (2)151 (2)
O31T—H31T···O25iii0.87 (3)2.04 (3)2.833 (2)152 (2)
O41T—H41T···O11Ti0.98 (2)1.61 (2)2.5415 (19)157 (2)
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x1/2, y+3/2, z+1; (iii) x, y, z+1.
 

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