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The crystal structures of brucine (2,3-di­methoxy­strychnidin-10-one), C23H26N2O4, brucine acetone solvate, C23H26N2O4·C3H6O, and brucine 2-propanol solvate dihydrate, C23H26N2O4·C3H7O·2H2O, have been determined. Crystals of brucine and its 2-propanol solvate dihydrate exhibit similar monolayer sheet packing, whereas crystals of the acetone solvate adopt a different mode of packing, as brucine pillars. The solvent appears to control the brucine self-assembly on the basis of common donor-acceptor properties of the surfaces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104024874/sq1174sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104024874/sq1174Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104024874/sq1174IIsup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104024874/sq1174IIIsup4.hkl
Contains datablock 3

CCDC references: 197896; 239488; 239489

Comment top

In a recent paper (Białońska & Ciunik, 2004) we reported molecular recognition during racemic resolution by fractional crystallization. Different donor–acceptor capabilities of N-benzoyl- (Gould & Walkinshaw, 1984) and N-phthaloyl-α-alanine determine various brucine or strychnine self-assemblies, and these last recognize the D– or L-enantiomer of alanine derivatives. These crystallizations were carried out from mixtures containing an alkaloid, a racemic alanine derivative and a solvent. Since the solvent plays an important role in molecular recognition and therefore in racemic resolution (Lehn, 1995; Jacques et al., 1991), our further studies are focused on its influence for crystallization of brucine. For clarity, we use acetone and 2-propanol as solvents, which have similar sizes but different chemical properties.

Views of the molecules, with the atom-numbering schemes, are presented in Fig. 1. The crystal structure of unsolvated brucine, (I), consists of corrugated monolayer sheets of brucine (Fig. 2) that are parallel to the (001) plane. The c cell dimension reflects the distance between neighboring brucine sheets. Methoxyl atoms O2 and O3 and the arene ring are involved as acceptors in weak hydrogen bonds, stabillizing structure of the monolayer sheet. Carbonyl atom O4 and amine atom N2 are acceptors of weak hydrogen bonds to adjacent parallel sheets.

The molecular packing of the brucine acetone solvate, (II), consists of brucine pillars (Fig. 3). The carbonyl O atom of the brucine molecule, in the center of the pillar, is an acceptor of weak C—H···O hydrogen bonds. Amine N and methoxyl O atoms on the pillar surface are able to? accept weak hydrogen bonds from adjacent pillars. Cavities between the arene rings protruding from a pillar are occupied by acetone molecules, contributing to the C—H···π hydrogen bonds that form between acetone methyl groups and aromatic rings of brucine molecules.

Crystals of brucine propanol dihydrate, (III), are similar to those of (I) and brucine ethanol solvate dihydrate (Glover et al., 1985) in that they adopt brucine monolayer sheet packing. The methoxyl O atoms and arene ring of the brucine molecule play a similar role to those in (I), where the CH···O(methoxyl) and C—H···π (arene) contacts stabilize the sheets. However, in (III), antiparallel neighbouring brucine sheets are separated by columns of solvent molecules (propanol and water) extended through the crystal channels (Fig. 4). Carbonyl atom O4 and amine atom N2 are directed towards the channel, and both participate as acceptors in hydrogen bonds with solvent ribbons (Table 1).

The brucine monolayer sheets in (I) are linked by weak hydrogen bonds that are relatively easily displaced by stronger hydrogen bonds with cocrystallizing compounds in (III) and in various other crystals (Gould & Walkinshaw, 1984; Glover et al., 1985; Dijksma et al., 1998; Boiadjiev et al., 1992; Pinkerton, 1993; Tanaka et al., 2001). While 2-propanol may form strong hydrogen bonds with hydroxyl groups by both donation and acceptance, the acetone molecule is only able to form weak interactions, with the carbonyl O atom acting as an acceptor. Different donor–acceptor capabilities of both 2-propanol and acetone lead to different brucine self-assembly design. However, the donor–acceptor capabilities of brucine self-assembled surfaces in crystals of (II) and (III) correspond well to donor–acceptor properties of acetone and 2-propanol, respectively. Strong hydrogen bonds involving the carbonyl o and the amine N atoms are possible due to the structure of the brucine monolayer surface in (III). Closure of the carbonyl O atom into the pillar in (II) causes its surface to give limited possibilities for acceptance of hydrogen bonds and to be susceptible to weak intermolecular interactions.

Experimental top

Crystals of brucine (POCh, Poland), (I), were grown from acetone solution. After dissolving the crystals of (I) by heating in the mother liquid, crystals of brucine acetone solvate, (II), were obtained. Crystals of brucine 2-propanol solvate dihydrate, (III), were grown from 2-propanol solution. Crystals of (I), (II) and (III) suitable for X-ray diffraction measurements were obtained at room temperature.

Refinement top

H atoms were found in Δρ maps. H-atom parameters were refined with isotropic displacement parameters and, before the last cycle of refinement, were fixed. Friedel pairs were merged before the final refinement. The absolute configurations of (I), (II) and (III) were chosen on the basis of the known absolute configuration of brucine.

Computing details top

For all compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 1999); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Views of the crystal structures of (I), (II) and (III), with the atom-numbering schemes.
[Figure 2] Fig. 2. Brucine monolayer sheets in (I). Dashed lines represent C—H···N and CH···O(carbonyl) hydrogen bonds.
[Figure 3] Fig. 3. The molecular packing of (II).
[Figure 4] Fig. 4. The molecular packing of (III). Dashed lines represent O—H···N and O—H···O hydrogen bonds.
(I) 2,3-dimethoxystrychnidin-10-one top
Crystal data top
C23H26N2O4F(000) = 420
Mr = 394.46Dx = 1.382 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.992 (2) ÅCell parameters from 2231 reflections
b = 12.704 (3) Åθ = 3.5–27.0°
c = 9.471 (2) ŵ = 0.10 mm1
β = 99.68 (3)°T = 100 K
V = 947.9 (4) Å3Plate, colourless
Z = 20.30 × 0.25 × 0.25 mm
Data collection top
Kuma KM-4 CCD
diffractometer
2021 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 27.0°, θmin = 3.5°
ω scanh = 1010
5627 measured reflectionsk = 1611
2126 independent reflectionsl = 1212
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0318P)2 + 0.4569P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
2126 reflectionsΔρmax = 0.19 e Å3
262 parametersΔρmin = 0.22 e Å3
1 restraintAbsolute structure: from known structure
Primary atom site location: structure-invariant direct methods
Crystal data top
C23H26N2O4V = 947.9 (4) Å3
Mr = 394.46Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.992 (2) ŵ = 0.10 mm1
b = 12.704 (3) ÅT = 100 K
c = 9.471 (2) Å0.30 × 0.25 × 0.25 mm
β = 99.68 (3)°
Data collection top
Kuma KM-4 CCD
diffractometer
2021 reflections with I > 2σ(I)
5627 measured reflectionsRint = 0.032
2126 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0401 restraint
wR(F2) = 0.089H-atom parameters constrained
S = 1.10Δρmax = 0.19 e Å3
2126 reflectionsΔρmin = 0.22 e Å3
262 parametersAbsolute structure: from known structure
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
O10.7195 (2)0.09506 (15)0.8236 (2)0.0240 (4)
O20.8858 (2)0.49240 (14)1.28786 (17)0.0191 (4)
O30.7917 (2)0.59245 (15)1.05067 (18)0.0208 (4)
O40.8767 (3)0.09616 (16)1.24284 (19)0.0265 (4)
N10.8383 (3)0.15842 (18)1.0145 (2)0.0185 (5)
N20.6901 (3)0.22198 (19)0.5303 (2)0.0207 (5)
C10.8688 (3)0.3218 (2)1.1709 (3)0.0186 (5)
H10.90210.28051.26360.019*
C20.8541 (3)0.4302 (2)1.1673 (3)0.0168 (5)
C30.8060 (3)0.4855 (2)1.0380 (3)0.0164 (5)
C40.7749 (3)0.4305 (2)0.9092 (3)0.0189 (5)
H40.74340.47110.81180.024*
C50.7912 (3)0.3219 (2)0.9105 (3)0.0185 (5)
C60.8362 (3)0.2687 (2)1.0396 (3)0.0167 (5)
C70.7786 (3)0.24670 (19)0.7862 (3)0.0168 (5)
C80.7768 (3)0.1374 (2)0.8604 (3)0.0185 (5)
H80.85210.08660.82070.019*
C90.8306 (3)0.0820 (2)1.1137 (3)0.0203 (5)
C100.7635 (4)0.0242 (2)1.0566 (3)0.0241 (6)
H10A0.85930.07131.04880.039*
H10B0.71400.05911.13400.029*
C110.6394 (3)0.0275 (2)0.9124 (3)0.0222 (6)
H110.53280.06170.92510.022*
C120.6137 (4)0.1262 (2)0.6922 (3)0.0285 (6)
H12A0.49280.13980.71310.044*
H12B0.66100.19460.66940.034*
C130.6174 (4)0.0484 (2)0.5742 (3)0.0245 (6)
H130.67040.07410.49060.031*
C140.5669 (3)0.0509 (2)0.5798 (3)0.0226 (6)
C150.5901 (4)0.1302 (2)0.4662 (3)0.0240 (6)
H15A0.46890.15820.41630.032*
H15B0.65590.10060.39490.017*
C160.8719 (3)0.1943 (2)0.5708 (3)0.0209 (5)
H16A0.88930.11590.59140.019*
H16B0.93260.20800.48840.015*
C170.9328 (3)0.2548 (2)0.7076 (3)0.0193 (5)
H17A0.94620.33220.68960.021*
H17B1.03860.21980.76290.019*
C180.6052 (3)0.0832 (2)0.8523 (3)0.0200 (5)
H180.54240.12290.92160.019*
C190.4924 (3)0.0951 (2)0.7045 (3)0.0217 (5)
H190.37980.06060.71250.023*
C200.4640 (3)0.2143 (2)0.6826 (3)0.0218 (5)
H20A0.42350.24430.77000.025*
H20B0.36950.22650.59330.021*
C210.6304 (3)0.2647 (2)0.6607 (3)0.0195 (5)
H21A0.61140.34450.65330.017*
C220.9123 (3)0.4396 (2)1.4230 (3)0.0229 (6)
H22A0.81430.39221.43220.024*
H22B1.01880.40201.43350.019*
H22C0.92120.49561.50090.031*
C230.7396 (4)0.6499 (2)0.9210 (3)0.0238 (6)
H23A0.82100.63870.84850.027*
H23B0.62160.62790.87220.020*
H23C0.74040.72910.94690.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0279 (10)0.0186 (10)0.0244 (10)0.0013 (8)0.0015 (8)0.0005 (8)
O20.0269 (9)0.0153 (9)0.0150 (8)0.0000 (8)0.0026 (7)0.0001 (7)
O30.0292 (10)0.0138 (9)0.0190 (9)0.0010 (8)0.0026 (7)0.0032 (7)
O40.0400 (11)0.0223 (10)0.0176 (9)0.0014 (9)0.0059 (8)0.0009 (8)
N10.0222 (11)0.0162 (11)0.0171 (10)0.0006 (9)0.0030 (8)0.0001 (9)
N20.0251 (11)0.0187 (11)0.0172 (10)0.0003 (9)0.0005 (8)0.0023 (9)
C10.0200 (12)0.0191 (13)0.0170 (12)0.0009 (10)0.0033 (9)0.0026 (10)
C20.0153 (12)0.0195 (13)0.0155 (12)0.0025 (10)0.0021 (9)0.0014 (10)
C30.0194 (12)0.0120 (12)0.0185 (12)0.0003 (10)0.0051 (9)0.0032 (10)
C40.0203 (13)0.0173 (13)0.0187 (12)0.0011 (10)0.0020 (10)0.0029 (10)
C50.0202 (13)0.0178 (13)0.0177 (12)0.0000 (10)0.0035 (10)0.0007 (10)
C60.0174 (11)0.0133 (13)0.0192 (13)0.0002 (9)0.0027 (9)0.0013 (10)
C70.0203 (12)0.0125 (12)0.0171 (12)0.0003 (10)0.0017 (9)0.0009 (10)
C80.0208 (13)0.0183 (13)0.0156 (12)0.0009 (10)0.0010 (9)0.0027 (10)
C90.0223 (13)0.0194 (14)0.0207 (12)0.0038 (11)0.0078 (10)0.0038 (11)
C100.0328 (14)0.0153 (14)0.0234 (13)0.0015 (12)0.0028 (11)0.0047 (11)
C110.0209 (13)0.0197 (14)0.0269 (13)0.0028 (11)0.0065 (10)0.0036 (11)
C120.0384 (16)0.0183 (14)0.0258 (14)0.0064 (13)0.0030 (12)0.0019 (12)
C130.0292 (14)0.0204 (14)0.0222 (13)0.0028 (11)0.0000 (10)0.0009 (11)
C140.0222 (13)0.0201 (14)0.0230 (13)0.0024 (11)0.0031 (10)0.0004 (11)
C150.0301 (14)0.0190 (14)0.0212 (13)0.0020 (11)0.0007 (10)0.0021 (11)
C160.0261 (13)0.0207 (14)0.0158 (12)0.0001 (11)0.0035 (10)0.0000 (10)
C170.0236 (12)0.0174 (12)0.0171 (12)0.0005 (11)0.0042 (9)0.0022 (10)
C180.0202 (12)0.0181 (13)0.0213 (12)0.0003 (11)0.0026 (9)0.0007 (11)
C190.0208 (12)0.0187 (14)0.0247 (13)0.0009 (11)0.0007 (10)0.0001 (11)
C200.0222 (13)0.0187 (13)0.0236 (13)0.0032 (11)0.0015 (10)0.0011 (11)
C210.0219 (12)0.0176 (13)0.0185 (12)0.0008 (10)0.0019 (10)0.0009 (10)
C220.0276 (14)0.0236 (14)0.0170 (12)0.0024 (11)0.0018 (10)0.0024 (11)
C230.0319 (14)0.0184 (13)0.0203 (13)0.0038 (12)0.0019 (10)0.0047 (11)
Geometric parameters (Å, º) top
O1—C111.426 (3)C11—C181.525 (4)
O1—C121.437 (3)C11—H110.9812
O2—C21.376 (3)C12—C131.496 (4)
O2—C221.429 (3)C12—H12A1.0334
O3—C31.370 (3)C12—H12B0.9858
O3—C231.429 (3)C13—C141.329 (4)
O4—C91.230 (3)C13—H131.0132
N1—C91.360 (3)C14—C151.508 (4)
N1—C61.421 (3)C14—C191.517 (4)
N1—C81.484 (3)C15—H15A1.0650
N2—C161.481 (4)C15—H15B0.9978
N2—C151.484 (3)C16—C171.515 (4)
N2—C211.498 (3)C16—H16A1.0203
C1—C21.383 (4)C16—H16B1.0006
C1—C61.400 (4)C17—H17A1.0064
C1—H11.0190C17—H17B1.0191
C2—C31.408 (3)C18—C191.540 (3)
C3—C41.392 (4)C18—H181.0232
C4—C51.386 (4)C19—C201.539 (4)
C4—H41.0498C19—H191.0151
C5—C61.390 (4)C20—C211.521 (4)
C5—C71.506 (3)C20—H20A1.0125
C7—C171.546 (3)C20—H20B1.0464
C7—C211.548 (3)C21—H21A1.0256
C7—C81.557 (4)C22—H22A1.0037
C8—C181.525 (4)C22—H22B0.9665
C8—H80.9975C22—H22C1.0188
C9—C101.517 (4)C23—H23A1.0323
C10—C111.548 (4)C23—H23B1.0172
C10—H10A0.9836C23—H23C1.0344
C10—H10B0.9942
C11—O1—C12114.8 (2)C14—C13—C12123.6 (3)
C2—O2—C22116.9 (2)C14—C13—H13120.4
C3—O3—C23116.6 (2)C12—C13—H13115.8
C9—N1—C6125.8 (2)C13—C14—C15122.1 (3)
C9—N1—C8120.3 (2)C13—C14—C19123.0 (3)
C6—N1—C8109.3 (2)C15—C14—C19114.8 (2)
C16—N2—C15110.9 (2)N2—C15—C14110.8 (2)
C16—N2—C21107.9 (2)N2—C15—H15A107.8
C15—N2—C21113.4 (2)C14—C15—H15A109.2
C2—C1—C6117.1 (2)N2—C15—H15B105.3
C2—C1—H1122.9C14—C15—H15B111.9
C6—C1—H1120.0H15A—C15—H15B111.7
O2—C2—C1123.3 (2)N2—C16—C17105.1 (2)
O2—C2—C3114.9 (2)N2—C16—H16A112.2
C1—C2—C3121.9 (2)C17—C16—H16A108.5
O3—C3—C4124.7 (2)N2—C16—H16B109.9
O3—C3—C2115.7 (2)C17—C16—H16B116.8
C4—C3—C2119.6 (2)H16A—C16—H16B104.5
C5—C4—C3119.3 (2)C16—C17—C7102.2 (2)
C5—C4—H4120.3C16—C17—H17A112.2
C3—C4—H4120.3C7—C17—H17A105.3
C4—C5—C6120.2 (2)C16—C17—H17B109.7
C4—C5—C7129.1 (2)C7—C17—H17B112.5
C6—C5—C7110.6 (2)H17A—C17—H17B114.3
C5—C6—C1121.9 (2)C8—C18—C11107.1 (2)
C5—C6—N1109.9 (2)C8—C18—C19112.7 (2)
C1—C6—N1128.2 (2)C11—C18—C19118.1 (2)
C5—C7—C17112.3 (2)C8—C18—H18106.2
C5—C7—C21116.6 (2)C11—C18—H18106.9
C17—C7—C21100.91 (19)C19—C18—H18105.0
C5—C7—C8102.6 (2)C14—C19—C20109.1 (2)
C17—C7—C8110.2 (2)C14—C19—C18115.1 (2)
C21—C7—C8114.5 (2)C20—C19—C18105.6 (2)
N1—C8—C18106.06 (19)C14—C19—H19111.5
N1—C8—C7104.9 (2)C20—C19—H19108.8
C18—C8—C7117.1 (2)C18—C19—H19106.3
N1—C8—H8111.5C21—C20—C19108.7 (2)
C18—C8—H8106.5C21—C20—H20A111.1
C7—C8—H8110.8C19—C20—H20A108.7
O4—C9—N1122.8 (3)C21—C20—H20B110.9
O4—C9—C10120.9 (2)C19—C20—H20B108.9
N1—C9—C10116.3 (2)H20A—C20—H20B108.5
C9—C10—C11118.3 (2)N2—C21—C20111.5 (2)
C9—C10—H10A109.5N2—C21—C7105.7 (2)
C11—C10—H10A108.0C20—C21—C7114.0 (2)
C9—C10—H10B107.1N2—C21—H21A111.5
C11—C10—H10B111.3C20—C21—H21A107.6
H10A—C10—H10B101.3C7—C21—H21A106.5
O1—C11—C18113.9 (2)O2—C22—H22A111.0
O1—C11—C10104.6 (2)O2—C22—H22B108.6
C18—C11—C10110.6 (2)H22A—C22—H22B112.5
O1—C11—H11106.9O2—C22—H22C107.6
C18—C11—H11110.4H22A—C22—H22C108.5
C10—C11—H11110.2H22B—C22—H22C108.5
O1—C12—C13112.5 (2)O3—C23—H23A112.1
O1—C12—H12A108.2O3—C23—H23B111.3
C13—C12—H12A113.0H23A—C23—H23B107.4
O1—C12—H12B104.0O3—C23—H23C107.7
C13—C12—H12B111.2H23A—C23—H23C108.2
H12A—C12—H12B107.5H23B—C23—H23C110.1
C22—O2—C2—C18.7 (3)C12—O1—C11—C10168.9 (2)
C22—O2—C2—C3171.7 (2)C9—C10—C11—O1122.6 (3)
C6—C1—C2—O2178.6 (2)C9—C10—C11—C180.5 (3)
C6—C1—C2—C30.9 (4)C11—O1—C12—C1386.6 (3)
C23—O3—C3—C40.5 (4)O1—C12—C13—C1461.3 (4)
C23—O3—C3—C2178.8 (2)C12—C13—C14—C15173.2 (2)
O2—C2—C3—O32.3 (3)C12—C13—C14—C192.8 (4)
C1—C2—C3—O3178.1 (2)C16—N2—C15—C1474.2 (3)
O2—C2—C3—C4178.5 (2)C21—N2—C15—C1447.3 (3)
C1—C2—C3—C41.1 (4)C13—C14—C15—N2122.6 (3)
O3—C3—C4—C5179.0 (2)C19—C14—C15—N253.6 (3)
C2—C3—C4—C50.2 (4)C15—N2—C16—C17143.9 (2)
C3—C4—C5—C60.8 (4)C21—N2—C16—C1719.1 (3)
C3—C4—C5—C7174.4 (2)N2—C16—C17—C738.3 (2)
C4—C5—C6—C11.0 (4)C5—C7—C17—C16166.7 (2)
C7—C5—C6—C1175.1 (2)C21—C7—C17—C1641.7 (2)
C4—C5—C6—N1177.7 (2)C8—C7—C17—C1679.6 (2)
C7—C5—C6—N16.3 (3)N1—C8—C18—C1171.5 (3)
C2—C1—C6—C50.1 (4)C7—C8—C18—C11171.9 (2)
C2—C1—C6—N1178.3 (2)N1—C8—C18—C19157.0 (2)
C9—N1—C6—C5160.9 (2)C7—C8—C18—C1940.4 (3)
C8—N1—C6—C55.0 (3)O1—C11—C18—C869.4 (3)
C9—N1—C6—C117.6 (4)C10—C11—C18—C848.0 (3)
C8—N1—C6—C1173.5 (2)O1—C11—C18—C1959.0 (3)
C4—C5—C7—C1771.4 (3)C10—C11—C18—C19176.5 (2)
C6—C5—C7—C17104.2 (2)C13—C14—C19—C20174.6 (2)
C4—C5—C7—C2144.4 (4)C15—C14—C19—C201.6 (3)
C6—C5—C7—C21140.0 (2)C13—C14—C19—C1856.1 (4)
C4—C5—C7—C8170.3 (3)C15—C14—C19—C18120.1 (3)
C6—C5—C7—C814.1 (3)C8—C18—C19—C1459.4 (3)
C9—N1—C8—C1846.4 (3)C11—C18—C19—C1466.4 (3)
C6—N1—C8—C18111.0 (2)C8—C18—C19—C2061.0 (3)
C9—N1—C8—C7171.0 (2)C11—C18—C19—C20173.2 (2)
C6—N1—C8—C713.5 (3)C14—C19—C20—C2154.4 (3)
C5—C7—C8—N116.1 (2)C18—C19—C20—C2170.0 (3)
C17—C7—C8—N1103.7 (2)C16—N2—C21—C20132.2 (2)
C21—C7—C8—N1143.5 (2)C15—N2—C21—C208.9 (3)
C5—C7—C8—C18101.1 (2)C16—N2—C21—C77.8 (3)
C17—C7—C8—C18139.1 (2)C15—N2—C21—C7115.5 (2)
C21—C7—C8—C1826.2 (3)C19—C20—C21—N261.4 (3)
C6—N1—C9—O425.0 (4)C19—C20—C21—C758.3 (3)
C8—N1—C9—O4178.5 (2)C5—C7—C21—N2152.6 (2)
C6—N1—C9—C10155.8 (3)C17—C7—C21—N230.6 (2)
C8—N1—C9—C102.3 (3)C8—C7—C21—N287.7 (3)
O4—C9—C10—C11153.9 (2)C5—C7—C21—C2084.6 (3)
N1—C9—C10—C1126.9 (4)C17—C7—C21—C20153.4 (2)
C12—O1—C11—C1870.2 (3)C8—C7—C21—C2035.1 (3)
(II) 2,3-dimethoxystrychnidin-10-one acetone solvate top
Crystal data top
C23H26N2O4·C3H6OF(000) = 484
Mr = 452.54Dx = 1.323 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 12.765 (3) ÅCell parameters from 7521 reflections
b = 7.1360 (14) Åθ = 3.7–30.0°
c = 13.686 (3) ŵ = 0.09 mm1
β = 114.35 (3)°T = 100 K
V = 1135.8 (4) Å3Block, colourless
Z = 20.25 × 0.25 × 0.20 mm
Data collection top
Kuma KM-4 CCD
diffractometer
3412 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 30.0°, θmin = 3.7°
ω scanh = 1717
14702 measured reflectionsk = 710
3499 independent reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.058P)2 + 0.1072P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
3499 reflectionsΔρmax = 0.35 e Å3
298 parametersΔρmin = 0.20 e Å3
1 restraintAbsolute structure: from known structure
Primary atom site location: structure-invariant direct methods
Crystal data top
C23H26N2O4·C3H6OV = 1135.8 (4) Å3
Mr = 452.54Z = 2
Monoclinic, P21Mo Kα radiation
a = 12.765 (3) ŵ = 0.09 mm1
b = 7.1360 (14) ÅT = 100 K
c = 13.686 (3) Å0.25 × 0.25 × 0.20 mm
β = 114.35 (3)°
Data collection top
Kuma KM-4 CCD
diffractometer
3412 reflections with I > 2σ(I)
14702 measured reflectionsRint = 0.023
3499 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0301 restraint
wR(F2) = 0.081H-atom parameters constrained
S = 1.05Δρmax = 0.35 e Å3
3499 reflectionsΔρmin = 0.20 e Å3
298 parametersAbsolute structure: from known structure
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
O10.20202 (7)0.84329 (16)0.62098 (7)0.01909 (19)
O20.46740 (7)0.74598 (16)0.59011 (7)0.0192 (2)
O30.56432 (7)0.78149 (17)0.79570 (7)0.0200 (2)
O40.03127 (7)0.80242 (14)0.42777 (7)0.01571 (18)
N10.09290 (8)0.89447 (15)0.60258 (7)0.01126 (18)
N20.13778 (9)0.99105 (15)0.94933 (8)0.01240 (19)
C10.27666 (9)0.82368 (19)0.57999 (8)0.0127 (2)
H10.23810.80760.50010.013*
C20.39497 (10)0.79816 (18)0.63658 (9)0.0136 (2)
C30.44846 (9)0.81867 (19)0.74958 (9)0.0138 (2)
C40.38393 (9)0.86991 (18)0.80611 (9)0.0129 (2)
H40.42200.88730.88310.021*
C50.26548 (9)0.89605 (17)0.74979 (9)0.0108 (2)
C60.21350 (9)0.87135 (17)0.63953 (9)0.0111 (2)
C70.17850 (9)0.95351 (16)0.79250 (9)0.0100 (2)
C80.06224 (9)0.90999 (17)0.69608 (8)0.0107 (2)
H80.00981.01300.68440.015*
C90.01080 (10)0.83540 (18)0.50657 (9)0.0125 (2)
C100.10891 (9)0.8210 (2)0.50473 (9)0.0152 (2)
H10A0.15390.75900.43940.015*
H10B0.13050.95340.50190.034*
C110.11740 (10)0.73107 (19)0.60445 (10)0.0147 (2)
H110.14640.60740.59010.018*
C120.23319 (11)0.7764 (2)0.70501 (11)0.0221 (3)
H12A0.22250.63700.71230.032*
H12B0.31530.81160.68260.025*
C130.15592 (11)0.8582 (2)0.81192 (10)0.0187 (2)
H130.18440.95070.84390.025*
C140.04417 (10)0.81492 (19)0.86031 (9)0.0144 (2)
C150.03805 (10)0.90876 (19)0.96228 (9)0.0145 (2)
H15A0.06840.81641.02450.018*
H15B0.00041.00800.98300.020*
C160.10836 (10)1.16577 (18)0.88598 (9)0.0130 (2)
H16A0.02801.16760.83520.020*
H16B0.12521.27300.93200.017*
C170.18295 (10)1.16256 (18)0.82253 (9)0.0121 (2)
H17A0.14721.25080.75670.014*
H17B0.25951.20160.86360.019*
C180.00202 (10)0.72591 (17)0.69891 (9)0.0121 (2)
H180.04370.62790.67900.022*
C190.01140 (10)0.67502 (18)0.81178 (9)0.0132 (2)
H190.02440.55920.80940.019*
C200.14115 (10)0.66348 (18)0.88440 (9)0.0134 (2)
H20A0.17760.58490.85160.013*
H20B0.15410.61020.95520.022*
C210.19243 (9)0.85962 (17)0.89880 (9)0.0116 (2)
H210.27690.84720.94610.020*
C220.41717 (12)0.7196 (3)0.47647 (11)0.0272 (3)
H22A0.35740.62170.45500.023*
H22B0.48110.68570.46060.025*
H22C0.38100.83030.43820.039*
C230.61798 (10)0.7820 (2)0.91084 (10)0.0224 (3)
H23A0.69550.73110.92820.029*
H23B0.57960.70920.94390.017*
H23C0.61950.90550.93770.019*
O50.50525 (10)0.3384 (2)0.90311 (9)0.0365 (3)
C240.50798 (12)0.3265 (2)0.81547 (11)0.0246 (3)
C250.39991 (13)0.3376 (2)0.71355 (11)0.0261 (3)
H25A0.33500.39100.73000.036*
H25B0.40800.41610.65860.042*
H25C0.37890.21460.68480.040*
C260.61886 (13)0.2968 (3)0.80320 (12)0.0370 (4)
H26A0.68350.29700.87190.030*
H26B0.61140.17860.76020.034*
H26C0.62740.39380.75750.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0121 (3)0.0264 (5)0.0199 (4)0.0027 (4)0.0078 (3)0.0003 (4)
O20.0143 (4)0.0318 (5)0.0135 (4)0.0038 (4)0.0079 (3)0.0004 (4)
O30.0096 (4)0.0369 (6)0.0128 (4)0.0043 (4)0.0037 (3)0.0027 (4)
O40.0158 (4)0.0183 (4)0.0120 (3)0.0012 (3)0.0046 (3)0.0022 (3)
N10.0095 (4)0.0133 (4)0.0102 (4)0.0002 (4)0.0033 (3)0.0015 (3)
N20.0143 (4)0.0113 (4)0.0138 (4)0.0003 (4)0.0080 (3)0.0002 (4)
C10.0127 (4)0.0144 (5)0.0107 (4)0.0004 (4)0.0047 (4)0.0007 (4)
C20.0130 (5)0.0170 (6)0.0126 (4)0.0012 (4)0.0071 (4)0.0016 (4)
C30.0098 (4)0.0180 (6)0.0130 (5)0.0014 (4)0.0040 (4)0.0018 (4)
C40.0109 (4)0.0161 (5)0.0106 (4)0.0003 (4)0.0031 (4)0.0003 (4)
C50.0106 (4)0.0110 (5)0.0105 (4)0.0007 (4)0.0043 (4)0.0003 (4)
C60.0103 (4)0.0115 (5)0.0106 (4)0.0000 (4)0.0033 (4)0.0001 (4)
C70.0097 (4)0.0101 (5)0.0098 (4)0.0008 (4)0.0037 (4)0.0011 (4)
C80.0104 (4)0.0116 (5)0.0101 (4)0.0002 (4)0.0042 (4)0.0010 (4)
C90.0117 (4)0.0115 (5)0.0117 (4)0.0001 (4)0.0023 (4)0.0007 (4)
C100.0106 (4)0.0189 (6)0.0138 (5)0.0007 (4)0.0028 (4)0.0019 (5)
C110.0110 (5)0.0157 (6)0.0164 (5)0.0022 (4)0.0046 (4)0.0028 (4)
C120.0124 (5)0.0335 (8)0.0223 (6)0.0047 (5)0.0089 (5)0.0030 (6)
C130.0157 (5)0.0233 (6)0.0201 (5)0.0007 (5)0.0104 (4)0.0012 (5)
C140.0158 (5)0.0137 (5)0.0168 (5)0.0019 (4)0.0097 (4)0.0001 (4)
C150.0153 (5)0.0151 (5)0.0160 (5)0.0011 (4)0.0092 (4)0.0017 (4)
C160.0156 (5)0.0101 (5)0.0143 (5)0.0003 (4)0.0072 (4)0.0013 (4)
C170.0131 (4)0.0107 (5)0.0128 (4)0.0014 (4)0.0058 (4)0.0016 (4)
C180.0115 (4)0.0110 (5)0.0137 (5)0.0013 (4)0.0050 (4)0.0018 (4)
C190.0143 (5)0.0111 (5)0.0155 (5)0.0010 (4)0.0072 (4)0.0004 (4)
C200.0150 (5)0.0107 (5)0.0145 (5)0.0005 (4)0.0060 (4)0.0015 (4)
C210.0128 (4)0.0116 (5)0.0110 (4)0.0005 (4)0.0054 (4)0.0001 (4)
C220.0217 (6)0.0472 (10)0.0147 (5)0.0059 (6)0.0097 (5)0.0017 (6)
C230.0130 (5)0.0379 (8)0.0130 (5)0.0032 (5)0.0022 (4)0.0031 (5)
O50.0351 (6)0.0546 (9)0.0206 (5)0.0084 (6)0.0123 (4)0.0019 (6)
C240.0255 (6)0.0265 (7)0.0189 (5)0.0057 (6)0.0060 (5)0.0008 (6)
C250.0264 (6)0.0233 (7)0.0221 (6)0.0037 (6)0.0035 (5)0.0038 (6)
C260.0271 (7)0.0614 (13)0.0209 (6)0.0029 (8)0.0082 (6)0.0044 (8)
Geometric parameters (Å, º) top
O1—C111.4356 (15)C12—H12B0.9951
O1—C121.4443 (16)C13—C141.3378 (17)
O2—C21.3721 (14)C13—H130.9439
O2—C221.4294 (16)C14—C151.5132 (17)
O3—C31.3735 (14)C14—C191.5262 (17)
O3—C231.4360 (15)C15—H15A1.0190
O4—C91.2326 (15)C15—H15B0.9683
N1—C91.3663 (15)C16—C171.5307 (16)
N1—C61.4182 (14)C16—H16A0.9735
N1—C81.4886 (14)C16—H16B0.9578
N2—C161.4761 (16)C17—H17A1.0380
N2—C151.4776 (15)C17—H17B0.9466
N2—C211.4974 (15)C18—C191.5427 (16)
C1—C21.3961 (16)C18—H180.9833
C1—C61.4040 (15)C19—C201.5428 (17)
C1—H11.0037C19—H190.9380
C2—C31.4173 (15)C20—C211.5231 (17)
C3—C41.3915 (16)C20—H20A0.9514
C4—C51.3978 (15)C20—H20B0.9893
C4—H40.9695C21—H211.0069
C5—C61.3867 (15)C22—H22A0.9857
C5—C71.5092 (15)C22—H22B0.9580
C7—C171.5422 (17)C22—H22C0.9551
C7—C211.5439 (16)C23—H23A0.9874
C7—C81.5574 (16)C23—H23B0.9484
C8—C181.5305 (17)C23—H23C0.9517
C8—H80.9623O5—C241.2172 (18)
C9—C101.5213 (16)C24—C251.506 (2)
C10—C111.5517 (17)C24—C261.507 (2)
C10—H10A0.9495C25—H25A1.0185
C10—H10B0.9803C25—H25B0.9762
C11—C181.5399 (17)C25—H25C0.9536
C11—H110.9457C26—H26A0.9616
C12—C131.5048 (19)C26—H26B1.0103
C12—H12A1.0035C26—H26C0.9689
C11—O1—C12114.42 (11)C14—C15—H15A111.4
C2—O2—C22117.02 (10)N2—C15—H15B108.1
C3—O3—C23116.09 (10)C14—C15—H15B110.6
C9—N1—C6126.62 (10)H15A—C15—H15B107.0
C9—N1—C8118.71 (9)N2—C16—C17104.68 (9)
C6—N1—C8109.49 (9)N2—C16—H16A111.7
C16—N2—C15112.52 (10)C17—C16—H16A108.3
C16—N2—C21108.18 (9)N2—C16—H16B110.8
C15—N2—C21113.27 (10)C17—C16—H16B111.2
C2—C1—C6117.28 (10)H16A—C16—H16B110.1
C2—C1—H1121.5C16—C17—C7101.68 (9)
C6—C1—H1121.3C16—C17—H17A109.2
O2—C2—C1124.04 (10)C7—C17—H17A113.6
O2—C2—C3114.85 (10)C16—C17—H17B113.0
C1—C2—C3121.07 (10)C7—C17—H17B111.0
O3—C3—C4124.57 (10)H17A—C17—H17B108.3
O3—C3—C2115.12 (10)C8—C18—C11106.97 (10)
C4—C3—C2120.30 (10)C8—C18—C19113.26 (9)
C3—C4—C5118.83 (10)C11—C18—C19119.18 (10)
C3—C4—H4119.5C8—C18—H18105.6
C5—C4—H4121.7C11—C18—H18104.2
C6—C5—C4120.44 (11)C19—C18—H18106.4
C6—C5—C7110.96 (10)C14—C19—C18115.06 (10)
C4—C5—C7128.60 (10)C14—C19—C20108.82 (10)
C5—C6—C1122.06 (10)C18—C19—C20106.09 (9)
C5—C6—N1109.59 (10)C14—C19—H19106.5
C1—C6—N1128.31 (10)C18—C19—H19109.7
C5—C7—C17114.45 (10)C20—C19—H19110.7
C5—C7—C21115.46 (9)C21—C20—C19108.92 (10)
C17—C7—C21101.03 (9)C21—C20—H20A109.6
C5—C7—C8102.35 (9)C19—C20—H20A109.4
C17—C7—C8109.65 (9)C21—C20—H20B109.7
C21—C7—C8114.28 (9)C19—C20—H20B110.7
N1—C8—C18105.71 (9)H20A—C20—H20B108.6
N1—C8—C7104.29 (9)N2—C21—C20112.21 (9)
C18—C8—C7117.57 (9)N2—C21—C7105.59 (9)
N1—C8—H8109.0C20—C21—C7113.61 (9)
C18—C8—H8109.7N2—C21—H21109.7
C7—C8—H8110.1C20—C21—H21106.9
O4—C9—N1123.03 (11)C7—C21—H21108.7
O4—C9—C10123.12 (10)O2—C22—H22A111.2
N1—C9—C10113.81 (10)O2—C22—H22B103.8
C9—C10—C11116.57 (10)H22A—C22—H22B112.3
C9—C10—H10A105.1O2—C22—H22C112.7
C11—C10—H10A113.6H22A—C22—H22C106.5
C9—C10—H10B101.5H22B—C22—H22C110.4
C11—C10—H10B108.3O3—C23—H23A103.9
H10A—C10—H10B111.1O3—C23—H23B114.6
O1—C11—C18115.45 (10)H23A—C23—H23B110.4
O1—C11—C10103.77 (10)O3—C23—H23C110.6
C18—C11—C10110.14 (9)H23A—C23—H23C112.9
O1—C11—H11107.3H23B—C23—H23C104.8
C18—C11—H11108.6O5—C24—C25121.43 (14)
C10—C11—H11111.5O5—C24—C26121.96 (13)
O1—C12—C13111.14 (11)C25—C24—C26116.60 (12)
O1—C12—H12A109.7C24—C25—H25A109.5
C13—C12—H12A106.3C24—C25—H25B113.3
O1—C12—H12B105.8H25A—C25—H25B108.0
C13—C12—H12B112.7C24—C25—H25C109.2
H12A—C12—H12B111.3H25A—C25—H25C108.6
C14—C13—C12121.97 (12)H25B—C25—H25C108.1
C14—C13—H13117.9C24—C26—H26A110.9
C12—C13—H13119.9C24—C26—H26B108.4
C13—C14—C15123.16 (12)H26A—C26—H26B114.1
C13—C14—C19121.84 (11)C24—C26—H26C109.4
C15—C14—C19114.88 (10)H26A—C26—H26C110.5
N2—C15—C14111.68 (10)H26B—C26—H26C103.2
N2—C15—H15A107.9
C22—O2—C2—C11.0 (2)C12—O1—C11—C10174.71 (10)
C22—O2—C2—C3178.74 (13)C9—C10—C11—O1140.38 (11)
C6—C1—C2—O2177.98 (12)C9—C10—C11—C1816.25 (15)
C6—C1—C2—C30.37 (19)C11—O1—C12—C1389.08 (14)
C23—O3—C3—C45.2 (2)O1—C12—C13—C1467.07 (18)
C23—O3—C3—C2173.67 (12)C12—C13—C14—C15173.89 (12)
O2—C2—C3—O30.63 (17)C12—C13—C14—C191.9 (2)
C1—C2—C3—O3177.19 (12)C16—N2—C15—C1475.06 (13)
O2—C2—C3—C4179.57 (12)C21—N2—C15—C1448.02 (13)
C1—C2—C3—C41.7 (2)C13—C14—C15—N2124.67 (13)
O3—C3—C4—C5177.28 (12)C19—C14—C15—N251.42 (14)
C2—C3—C4—C51.56 (19)C15—N2—C16—C17145.15 (10)
C3—C4—C5—C60.04 (19)C21—N2—C16—C1719.27 (12)
C3—C4—C5—C7179.13 (12)N2—C16—C17—C738.70 (11)
C4—C5—C6—C11.37 (19)C5—C7—C17—C16167.12 (9)
C7—C5—C6—C1177.87 (11)C21—C7—C17—C1642.39 (11)
C4—C5—C6—N1176.41 (11)C8—C7—C17—C1678.57 (10)
C7—C5—C6—N14.34 (14)N1—C8—C18—C1172.37 (11)
C2—C1—C6—C51.18 (19)C7—C8—C18—C11171.78 (9)
C2—C1—C6—N1176.16 (12)N1—C8—C18—C19154.31 (9)
C9—N1—C6—C5161.93 (12)C7—C8—C18—C1938.46 (13)
C8—N1—C6—C58.05 (14)O1—C11—C18—C877.85 (12)
C9—N1—C6—C115.7 (2)C10—C11—C18—C839.23 (13)
C8—N1—C6—C1169.56 (12)O1—C11—C18—C1952.19 (15)
C6—C5—C7—C17104.54 (12)C10—C11—C18—C19169.27 (11)
C4—C5—C7—C1774.62 (16)C13—C14—C19—C1858.68 (16)
C6—C5—C7—C21138.76 (11)C15—C14—C19—C18117.47 (12)
C4—C5—C7—C2142.07 (18)C13—C14—C19—C20177.53 (12)
C6—C5—C7—C813.99 (13)C15—C14—C19—C201.38 (14)
C4—C5—C7—C8166.85 (13)C8—C18—C19—C1462.11 (13)
C9—N1—C8—C1848.04 (13)C11—C18—C19—C1465.05 (14)
C6—N1—C8—C18108.21 (10)C8—C18—C19—C2058.26 (12)
C9—N1—C8—C7172.63 (10)C11—C18—C19—C20174.58 (10)
C6—N1—C8—C716.38 (12)C14—C19—C20—C2155.28 (12)
C5—C7—C8—N117.65 (11)C18—C19—C20—C2169.06 (12)
C17—C7—C8—N1104.22 (10)C16—N2—C21—C20132.18 (10)
C21—C7—C8—N1143.20 (10)C15—N2—C21—C206.73 (13)
C5—C7—C8—C1898.97 (11)C16—N2—C21—C77.90 (12)
C17—C7—C8—C18139.16 (10)C15—N2—C21—C7117.54 (11)
C21—C7—C8—C1826.58 (14)C19—C20—C21—N259.90 (12)
C6—N1—C9—O421.5 (2)C19—C20—C21—C759.80 (12)
C8—N1—C9—O4173.29 (12)C5—C7—C21—N2155.39 (9)
C6—N1—C9—C10160.58 (12)C17—C7—C21—N231.34 (11)
C8—N1—C9—C108.82 (16)C8—C7—C21—N286.28 (11)
O4—C9—C10—C11138.74 (13)C5—C7—C21—C2081.22 (12)
N1—C9—C10—C1143.37 (16)C17—C7—C21—C20154.74 (9)
C12—O1—C11—C1864.68 (14)C8—C7—C21—C2037.11 (13)
(III) 2,3-dimethoxystrychnidin-10-one 2-propanol solvate dihydrate top
Crystal data top
C23H26N2O4·C3H8O·2H2ODx = 1.325 Mg m3
Mr = 490.58Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 6099 reflections
a = 7.9297 (3) Åθ = 3.2–27.5°
b = 12.3289 (7) ŵ = 0.10 mm1
c = 25.1631 (10) ÅT = 100 K
V = 2460.06 (19) Å3Block, colourless
Z = 40.50 × 0.40 × 0.40 mm
F(000) = 1056
Data collection top
Kuma KM-4 CCD
diffractometer
3019 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 3.2°
ω scanh = 1010
16487 measured reflectionsk = 1216
3185 independent reflectionsl = 3132
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.0468P)2 + 0.3452P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
3185 reflectionsΔρmax = 0.27 e Å3
316 parametersΔρmin = 0.15 e Å3
0 restraintsAbsolute structure: from known structure
Primary atom site location: structure-invariant direct methods
Crystal data top
C23H26N2O4·C3H8O·2H2OV = 2460.06 (19) Å3
Mr = 490.58Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.9297 (3) ŵ = 0.10 mm1
b = 12.3289 (7) ÅT = 100 K
c = 25.1631 (10) Å0.50 × 0.40 × 0.40 mm
Data collection top
Kuma KM-4 CCD
diffractometer
3019 reflections with I > 2σ(I)
16487 measured reflectionsRint = 0.028
3185 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.074H-atom parameters constrained
S = 1.06Δρmax = 0.27 e Å3
3185 reflectionsΔρmin = 0.15 e Å3
316 parametersAbsolute structure: from known structure
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
O10.23144 (15)0.51181 (9)0.33192 (4)0.0189 (2)
O20.17650 (15)1.09858 (8)0.14223 (4)0.0170 (2)
O30.23853 (15)1.21113 (8)0.22681 (4)0.0173 (2)
O40.16424 (16)0.69525 (9)0.17113 (4)0.0216 (2)
N10.15614 (17)0.76820 (10)0.25401 (5)0.0144 (3)
N20.22204 (18)0.85524 (11)0.43108 (5)0.0186 (3)
C10.16244 (19)0.92874 (12)0.19113 (6)0.0152 (3)
H10.14540.88870.15930.014*
C20.1843 (2)1.04026 (12)0.18844 (6)0.0146 (3)
C30.21532 (19)1.10228 (12)0.23486 (6)0.0150 (3)
C40.21924 (19)1.05148 (12)0.28420 (6)0.0154 (3)
H40.23591.09530.31650.018*
C50.19594 (19)0.93975 (12)0.28701 (5)0.0143 (3)
C60.16979 (19)0.87991 (12)0.24107 (6)0.0142 (3)
C70.1799 (2)0.86890 (11)0.33556 (5)0.0140 (3)
C80.18818 (19)0.75230 (12)0.31176 (5)0.0136 (3)
H80.09870.70500.32600.018*
C90.1806 (2)0.68471 (12)0.21950 (6)0.0161 (3)
C100.2305 (2)0.57641 (12)0.24344 (6)0.0180 (3)
H10A0.13030.53640.25000.020*
H10B0.29440.53910.21620.022*
C110.3293 (2)0.57650 (12)0.29639 (6)0.0161 (3)
H110.43780.54190.29120.018*
C120.3153 (2)0.48521 (13)0.38102 (6)0.0227 (3)
H12A0.43900.47400.37330.022*
H12B0.26830.41500.39160.021*
C130.2884 (2)0.57142 (14)0.42283 (6)0.0222 (3)
H130.22570.54880.45330.028*
C140.3435 (2)0.67244 (13)0.41731 (6)0.0193 (3)
C150.3051 (2)0.76117 (13)0.45685 (6)0.0217 (3)
H15A0.22210.73460.48410.034*
H15B0.41580.78500.47400.029*
C160.0419 (2)0.83283 (13)0.41857 (6)0.0198 (3)
H16A0.03160.86320.44550.020*
H16B0.02680.75230.41670.019*
C170.0112 (2)0.88701 (13)0.36501 (6)0.0170 (3)
H17A0.08700.85620.34650.023*
H17B0.00610.96410.37040.014*
C180.35731 (19)0.69349 (12)0.31556 (6)0.0150 (3)
H180.43290.72590.28690.017*
C190.4451 (2)0.71034 (13)0.36937 (6)0.0175 (3)
H190.55610.67190.36790.023*
C200.4772 (2)0.83300 (13)0.37365 (6)0.0186 (3)
H20A0.55700.85150.40220.023*
H20B0.53520.86130.34100.023*
C210.3082 (2)0.88992 (12)0.38084 (6)0.0166 (3)
H210.32660.96730.38340.020*
C220.1644 (2)1.03768 (13)0.09384 (6)0.0211 (3)
H22A0.16721.09220.06550.021*
H22B0.25460.98690.09000.020*
H22C0.05480.99750.09330.032*
C230.2677 (2)1.27568 (13)0.27301 (6)0.0217 (3)
H23A0.27751.35100.26090.023*
H23B0.17781.27370.29800.027*
H23C0.37131.25250.29280.023*
O50.96333 (16)0.85804 (10)0.01511 (4)0.0244 (3)
H51.06060.88420.00430.039*
C240.8220 (3)0.93197 (14)0.06200 (7)0.0288 (4)
H24A0.75710.98570.04030.033*
H24B0.93710.96610.07340.040*
H24C0.76060.91470.09490.028*
C250.8648 (2)0.83044 (14)0.03123 (6)0.0214 (3)
H250.76120.80000.01800.023*
C260.9559 (2)0.74772 (14)0.06552 (7)0.0264 (4)
H26A0.97670.68100.04410.036*
H26B0.88440.72670.09650.021*
H26C1.06010.78310.08030.024*
O1W0.76915 (16)0.55833 (9)0.01781 (4)0.0248 (3)
H11W0.81780.60090.04360.039*
H12W0.77270.49080.03160.036*
O2W0.90769 (17)0.70439 (11)0.09222 (5)0.0298 (3)
H21W0.98540.69790.11580.039*
H22W0.93720.75640.06900.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0209 (5)0.0156 (5)0.0201 (5)0.0012 (4)0.0027 (5)0.0034 (4)
O20.0230 (6)0.0152 (5)0.0127 (5)0.0021 (5)0.0003 (4)0.0015 (4)
O30.0238 (6)0.0118 (5)0.0164 (5)0.0012 (4)0.0015 (4)0.0005 (4)
O40.0313 (6)0.0186 (5)0.0149 (5)0.0001 (5)0.0005 (5)0.0019 (4)
N10.0168 (6)0.0127 (6)0.0136 (5)0.0005 (5)0.0003 (5)0.0002 (5)
N20.0239 (7)0.0169 (6)0.0151 (6)0.0014 (6)0.0006 (5)0.0018 (5)
C10.0149 (7)0.0165 (7)0.0141 (6)0.0003 (6)0.0005 (6)0.0015 (5)
C20.0142 (7)0.0160 (7)0.0137 (6)0.0003 (6)0.0015 (6)0.0009 (5)
C30.0140 (7)0.0130 (7)0.0180 (7)0.0005 (6)0.0019 (6)0.0001 (5)
C40.0162 (7)0.0151 (7)0.0150 (6)0.0015 (6)0.0008 (6)0.0020 (6)
C50.0135 (7)0.0158 (7)0.0137 (6)0.0019 (6)0.0008 (5)0.0001 (5)
C60.0134 (7)0.0132 (7)0.0160 (6)0.0006 (6)0.0005 (6)0.0001 (5)
C70.0169 (7)0.0115 (6)0.0137 (6)0.0011 (6)0.0000 (6)0.0005 (5)
C80.0141 (7)0.0134 (6)0.0133 (6)0.0005 (6)0.0012 (5)0.0005 (5)
C90.0156 (7)0.0155 (7)0.0173 (6)0.0014 (6)0.0004 (6)0.0013 (6)
C100.0226 (8)0.0126 (7)0.0187 (7)0.0009 (6)0.0003 (6)0.0026 (6)
C110.0151 (7)0.0121 (6)0.0211 (7)0.0011 (6)0.0004 (6)0.0005 (5)
C120.0283 (8)0.0162 (7)0.0236 (7)0.0021 (7)0.0056 (7)0.0053 (6)
C130.0257 (8)0.0219 (8)0.0191 (7)0.0021 (7)0.0034 (6)0.0038 (6)
C140.0205 (7)0.0200 (7)0.0174 (7)0.0040 (7)0.0056 (6)0.0019 (6)
C150.0299 (9)0.0194 (7)0.0157 (7)0.0022 (7)0.0030 (6)0.0021 (6)
C160.0231 (8)0.0191 (7)0.0171 (7)0.0014 (7)0.0021 (6)0.0017 (6)
C170.0193 (7)0.0162 (7)0.0156 (7)0.0031 (6)0.0026 (6)0.0002 (6)
C180.0143 (7)0.0125 (7)0.0181 (7)0.0006 (6)0.0000 (6)0.0005 (5)
C190.0156 (7)0.0160 (7)0.0209 (7)0.0019 (6)0.0038 (6)0.0000 (6)
C200.0180 (7)0.0172 (7)0.0206 (7)0.0005 (6)0.0047 (6)0.0012 (6)
C210.0208 (8)0.0141 (7)0.0148 (7)0.0002 (6)0.0019 (6)0.0014 (5)
C220.0302 (9)0.0190 (7)0.0140 (6)0.0012 (7)0.0022 (7)0.0003 (6)
C230.0295 (9)0.0147 (7)0.0209 (7)0.0016 (7)0.0010 (7)0.0026 (6)
O50.0283 (6)0.0279 (6)0.0169 (5)0.0009 (5)0.0012 (5)0.0011 (5)
C240.0367 (10)0.0240 (8)0.0258 (8)0.0047 (8)0.0062 (8)0.0014 (7)
C250.0221 (8)0.0229 (8)0.0191 (7)0.0023 (7)0.0008 (6)0.0000 (6)
C260.0312 (9)0.0229 (8)0.0253 (8)0.0019 (8)0.0023 (7)0.0032 (7)
O1W0.0331 (7)0.0204 (6)0.0208 (5)0.0005 (5)0.0020 (5)0.0037 (5)
O2W0.0302 (7)0.0336 (7)0.0255 (6)0.0047 (6)0.0055 (5)0.0053 (5)
Geometric parameters (Å, º) top
O1—C111.4274 (18)C14—C151.509 (2)
O1—C121.4411 (19)C14—C191.524 (2)
O2—C21.3687 (17)C15—H15A1.0060
O2—C221.4337 (18)C15—H15B1.0207
O3—C31.3697 (18)C16—C171.524 (2)
O3—C231.4279 (18)C16—H16A0.9693
O4—C91.2311 (18)C16—H16B1.0013
N1—C91.3605 (19)C17—H17A0.9839
N1—C61.4192 (19)C17—H17B0.9698
N1—C81.4884 (17)C18—C191.537 (2)
N2—C151.483 (2)C18—H181.0189
N2—C161.488 (2)C19—C201.537 (2)
N2—C211.4995 (19)C19—H191.0004
C1—C21.387 (2)C20—C211.523 (2)
C1—C61.3947 (19)C20—H20A0.9845
C1—H10.9514C20—H20B1.0040
C2—C31.418 (2)C21—H210.9676
C3—C41.391 (2)C22—H22A0.9810
C4—C51.392 (2)C22—H22B0.9554
C4—H40.9842C22—H22C1.0005
C5—C61.387 (2)C23—H23A0.9804
C5—C71.5071 (19)C23—H23B0.9505
C7—C171.546 (2)C23—H23C1.0027
C7—C211.549 (2)O5—C251.4441 (19)
C7—C81.5587 (19)O5—H50.8790
C8—C181.528 (2)C24—C251.511 (2)
C8—H80.9854C24—H24A1.0016
C9—C101.517 (2)C24—H24B1.0452
C10—C111.546 (2)C24—H24C0.9832
C10—H10A0.9497C25—C261.519 (2)
C10—H10B0.9688C25—H250.9627
C11—C181.537 (2)C26—H26A0.9969
C11—H110.9687C26—H26B0.9987
C12—C131.511 (2)C26—H26C1.0051
C12—H12A1.0091O1W—H11W0.9207
C12—H12B0.9794O1W—H12W0.9024
C13—C141.327 (2)O2W—H21W0.8583
C13—H130.9549O2W—H22W0.8977
C11—O1—C12114.42 (12)H15A—C15—H15B111.6
C2—O2—C22116.71 (11)N2—C16—C17105.01 (13)
C3—O3—C23116.58 (11)N2—C16—H16A111.0
C9—N1—C6125.24 (12)C17—C16—H16A110.7
C9—N1—C8119.94 (12)N2—C16—H16B108.0
C6—N1—C8109.80 (11)C17—C16—H16B112.0
C15—N2—C16111.94 (13)H16A—C16—H16B110.1
C15—N2—C21112.89 (13)C16—C17—C7102.86 (12)
C16—N2—C21108.19 (12)C16—C17—H17A112.1
C2—C1—C6117.81 (14)C7—C17—H17A113.8
C2—C1—H1119.4C16—C17—H17B109.3
C6—C1—H1122.8C7—C17—H17B109.3
O2—C2—C1123.81 (13)H17A—C17—H17B109.3
O2—C2—C3115.12 (12)C8—C18—C19112.87 (12)
C1—C2—C3121.06 (14)C8—C18—C11107.39 (12)
O3—C3—C4124.77 (13)C19—C18—C11117.96 (12)
O3—C3—C2115.46 (13)C8—C18—H18106.6
C4—C3—C2119.76 (13)C19—C18—H18107.7
C3—C4—C5119.22 (14)C11—C18—H18103.3
C3—C4—H4119.5C14—C19—C18114.61 (12)
C5—C4—H4121.3C14—C19—C20109.49 (13)
C6—C5—C4120.26 (14)C18—C19—C20105.65 (12)
C6—C5—C7110.78 (12)C14—C19—H19110.4
C4—C5—C7128.76 (13)C18—C19—H19107.6
C5—C6—C1121.85 (13)C20—C19—H19108.8
C5—C6—N1109.66 (12)C21—C20—C19108.41 (13)
C1—C6—N1128.48 (13)C21—C20—H20A111.8
C5—C7—C17112.20 (12)C19—C20—H20A112.7
C5—C7—C21116.35 (12)C21—C20—H20B109.9
C17—C7—C21101.04 (11)C19—C20—H20B111.2
C5—C7—C8102.69 (11)H20A—C20—H20B102.8
C17—C7—C8110.71 (12)N2—C21—C20111.69 (12)
C21—C7—C8114.16 (12)N2—C21—C7105.84 (12)
N1—C8—C18105.87 (12)C20—C21—C7114.41 (12)
N1—C8—C7104.27 (11)N2—C21—H21107.1
C18—C8—C7116.78 (12)C20—C21—H21109.2
N1—C8—H8108.0C7—C21—H21108.2
C18—C8—H8109.2O2—C22—H22A104.9
C7—C8—H8112.1O2—C22—H22B112.3
O4—C9—N1122.42 (14)H22A—C22—H22B111.0
O4—C9—C10120.85 (13)O2—C22—H22C109.2
N1—C9—C10116.72 (12)H22A—C22—H22C110.5
C9—C10—C11118.28 (12)H22B—C22—H22C108.9
C9—C10—H10A107.9O3—C23—H23A106.7
C11—C10—H10A105.9O3—C23—H23B113.7
C9—C10—H10B105.8H23A—C23—H23B106.8
C11—C10—H10B110.2O3—C23—H23C112.3
H10A—C10—H10B108.3H23A—C23—H23C111.1
O1—C11—C18113.98 (12)H23B—C23—H23C106.1
O1—C11—C10105.31 (12)C25—O5—H5108.2
C18—C11—C10110.15 (12)C25—C24—H24A112.6
O1—C11—H11108.7C25—C24—H24B106.1
C18—C11—H11109.1H24A—C24—H24B109.4
C10—C11—H11109.5C25—C24—H24C111.3
O1—C12—C13111.82 (13)H24A—C24—H24C110.4
O1—C12—H12A108.3H24B—C24—H24C106.7
C13—C12—H12A111.6O5—C25—C24109.90 (14)
O1—C12—H12B104.9O5—C25—C26111.08 (14)
C13—C12—H12B112.3C24—C25—C26111.85 (14)
H12A—C12—H12B107.5O5—C25—H25105.9
C14—C13—C12122.75 (15)C24—C25—H25108.0
C14—C13—H13121.9C26—C25—H25109.9
C12—C13—H13115.3C25—C26—H26A109.0
C13—C14—C15123.02 (15)C25—C26—H26B110.4
C13—C14—C19122.99 (14)H26A—C26—H26B107.5
C15—C14—C19113.95 (13)C25—C26—H26C108.1
N2—C15—C14111.59 (12)H26A—C26—H26C115.0
N2—C15—H15A105.2H26B—C26—H26C106.9
C14—C15—H15A110.2H11W—O1W—H12W104.0
N2—C15—H15B110.0H21W—O2W—H22W109.1
C14—C15—H15B108.3
C22—O2—C2—C17.4 (2)C12—O1—C11—C10169.58 (12)
C22—O2—C2—C3173.19 (14)C9—C10—C11—O1123.88 (14)
C6—C1—C2—O2178.54 (14)C9—C10—C11—C180.56 (19)
C6—C1—C2—C30.8 (2)C11—O1—C12—C1387.71 (17)
C23—O3—C3—C40.4 (2)O1—C12—C13—C1463.2 (2)
C23—O3—C3—C2179.19 (13)C12—C13—C14—C15174.98 (15)
O2—C2—C3—O32.0 (2)C12—C13—C14—C192.5 (3)
C1—C2—C3—O3178.56 (14)C16—N2—C15—C1475.35 (17)
O2—C2—C3—C4177.54 (14)C21—N2—C15—C1447.02 (18)
C1—C2—C3—C41.9 (2)C13—C14—C15—N2123.71 (17)
O3—C3—C4—C5179.16 (14)C19—C14—C15—N253.94 (19)
C2—C3—C4—C51.3 (2)C15—N2—C16—C17141.76 (13)
C3—C4—C5—C60.2 (2)C21—N2—C16—C1716.74 (16)
C3—C4—C5—C7174.14 (15)N2—C16—C17—C736.18 (15)
C4—C5—C6—C11.3 (2)C5—C7—C17—C16165.39 (12)
C7—C5—C6—C1174.00 (14)C21—C7—C17—C1640.77 (13)
C4—C5—C6—N1177.74 (14)C8—C7—C17—C1680.54 (14)
C7—C5—C6—N16.94 (18)N1—C8—C18—C19156.66 (12)
C2—C1—C6—C50.8 (2)C7—C8—C18—C1941.16 (17)
C2—C1—C6—N1178.09 (15)N1—C8—C18—C1171.63 (14)
C9—N1—C6—C5159.18 (14)C7—C8—C18—C11172.87 (12)
C8—N1—C6—C54.51 (17)O1—C11—C18—C870.27 (15)
C9—N1—C6—C119.8 (3)C10—C11—C18—C847.83 (15)
C8—N1—C6—C1174.47 (15)O1—C11—C18—C1958.58 (18)
C6—C5—C7—C17104.25 (15)C10—C11—C18—C19176.68 (13)
C4—C5—C7—C1770.6 (2)C13—C14—C19—C1857.4 (2)
C6—C5—C7—C21140.09 (14)C15—C14—C19—C18120.24 (15)
C4—C5—C7—C2145.1 (2)C13—C14—C19—C20175.90 (16)
C6—C5—C7—C814.66 (16)C15—C14—C19—C201.76 (18)
C4—C5—C7—C8170.53 (16)C8—C18—C19—C1459.02 (17)
C9—N1—C8—C1845.82 (17)C11—C18—C19—C1467.22 (18)
C6—N1—C8—C18110.39 (13)C8—C18—C19—C2061.60 (16)
C9—N1—C8—C7169.57 (13)C11—C18—C19—C20172.16 (13)
C6—N1—C8—C713.36 (16)C14—C19—C20—C2154.20 (16)
C5—C7—C8—N116.27 (14)C18—C19—C20—C2169.71 (15)
C17—C7—C8—N1103.68 (13)C15—N2—C21—C209.99 (17)
C21—C7—C8—N1143.12 (12)C16—N2—C21—C20134.44 (13)
C5—C7—C8—C18100.11 (14)C15—N2—C21—C7115.12 (13)
C17—C7—C8—C18139.94 (13)C16—N2—C21—C79.33 (16)
C21—C7—C8—C1826.73 (17)C19—C20—C21—N262.02 (16)
C6—N1—C9—O423.9 (3)C19—C20—C21—C758.20 (17)
C8—N1—C9—O4176.19 (14)C5—C7—C21—N2152.68 (12)
C6—N1—C9—C10155.84 (15)C17—C7—C21—N230.92 (14)
C8—N1—C9—C103.5 (2)C8—C7—C21—N287.93 (14)
O4—C9—C10—C11151.24 (15)C5—C7—C21—C2083.90 (16)
N1—C9—C10—C1128.5 (2)C17—C7—C21—C20154.34 (13)
C12—O1—C11—C1869.58 (16)C8—C7—C21—C2035.49 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O1Wi0.881.882.7622 (18)179.1
O1W—H11W···O2W0.921.902.8206 (18)172.7
O1W—H12W···N2ii0.901.922.8158 (17)173.3
O2W—H21W···O4iii0.861.992.8449 (17)175.6
O2W—H22W···O50.901.862.7474 (17)170.0
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x+1, y1/2, z+1/2; (iii) x+1, y, z.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC23H26N2O4C23H26N2O4·C3H6OC23H26N2O4·C3H8O·2H2O
Mr394.46452.54490.58
Crystal system, space groupMonoclinic, P21Monoclinic, P21Orthorhombic, P212121
Temperature (K)100100100
a, b, c (Å)7.992 (2), 12.704 (3), 9.471 (2)12.765 (3), 7.1360 (14), 13.686 (3)7.9297 (3), 12.3289 (7), 25.1631 (10)
α, β, γ (°)90, 99.68 (3), 9090, 114.35 (3), 9090, 90, 90
V3)947.9 (4)1135.8 (4)2460.06 (19)
Z224
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.100.090.10
Crystal size (mm)0.30 × 0.25 × 0.250.25 × 0.25 × 0.200.50 × 0.40 × 0.40
Data collection
DiffractometerKuma KM-4 CCD
diffractometer
Kuma KM-4 CCD
diffractometer
Kuma KM-4 CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5627, 2126, 2021 14702, 3499, 3412 16487, 3185, 3019
Rint0.0320.0230.028
(sin θ/λ)max1)0.6390.7030.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.089, 1.10 0.030, 0.081, 1.05 0.029, 0.074, 1.06
No. of reflections212634993185
No. of parameters262298316
No. of restraints110
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.220.35, 0.200.27, 0.15
Absolute structureFrom known structureFrom known structureFrom known structure

Computer programs: CrysAlis CCD (Oxford Diffraction, 2001), CrysAlis RED (Oxford Diffraction, 2001), CrysAlis RED, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-NT (Bruker, 1999), SHELXL97.

Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O1Wi0.881.882.7622 (18)179.1
O1W—H11W···O2W0.921.902.8206 (18)172.7
O1W—H12W···N2ii0.901.922.8158 (17)173.3
O2W—H21W···O4iii0.861.992.8449 (17)175.6
O2W—H22W···O50.901.862.7474 (17)170.0
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x+1, y1/2, z+1/2; (iii) x+1, y, z.
 

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