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C-Alkyl (including C-aryl­meth­yl) derivatives of Meldrum's acids are attractive building blocks in organic synthesis, mainly due to the unusually high acidity of the resulting compounds. Three examples, namely 5-[4-(di­ethyl­amino)­benz­yl]-2,2-dimethyl-1,3-dioxane-4,6-dione, C17H23NO4, (I), 2,2-dimethyl-5-(2,4,6-tri­meth­oxy­benz­yl)-1,3-dioxane-4,6-dione, C16H20O7, (II), and 5-(4-hy­droxy-3,5-di­meth­oxy­benz­yl)-2,2-dimethyl-1,3-dioxane-4,6-dione, C15H18O7, (III), have been synthesized, characterized by NMR and IR spectroscopy, and studied by single-crystal X-ray structure analysis. The nature of the different substituents resulted in remarkable differences in both the mol­ecular conformations and the crystal packing arrangements. The presence of a substituent with a basic centre in compound (I) leads to the formation of an inner salt accompanied by drastic changes in the conformation of the 1,3-dioxane-4,6-dione fragment. By virtue of strong N—H...O hydrogen bonds, the residues are assembled into infinite chains with the graph-set descriptor C(10). Compound (II) contains meth­oxy groups in both the ortho- and para-positions of the aryl­methyl fragment. Because of the absence of classical hydrogen-bond donors in this structure, the crystal packing is controlled by van der Waals forces and weak C—H...O inter­actions. Compound (III) contains meth­oxy groups in both meta-positions and a hy­droxy group in the para-position. Supra­molecular tetra­meric synthons which comprise hydrogen-bonded dimers associated into tetra­mers through π–π inter­actions of overlapping benzene rings were observed.

Supporting information

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Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615014308/dt3032sup1.cif
Contains datablocks I, II, III, global

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Structure factor file (CIF format) https://doi.org/10.1107/S2053229615014308/dt3032Isup2.hkl
Contains datablock I

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Structure factor file (CIF format) https://doi.org/10.1107/S2053229615014308/dt3032IIsup3.hkl
Contains datablock II

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Structure factor file (CIF format) https://doi.org/10.1107/S2053229615014308/dt3032IIIsup4.hkl
Contains datablock III

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Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615014308/dt3032Isup5.cml
Supplementary material

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Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615014308/dt3032IIsup6.cml
Supplementary material

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Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615014308/dt3032IIIsup7.cml
Supplementary material

CCDC references: 1415729; 1415728; 1415727

Introduction top

C-Alkyl (including C-aryl­methyl) derivatives of Meldrum's acids are attractive building blocks in organic synthesis (Mierina, 2013) that is mainly due to the unusually high acidity of the resulting compounds (Nakamura et al., 2004; Byun et al., 2001). Aryl­methyl Meldrum's acids show good and excellent anti­radical and anti­oxidant properties (Mierina et al., 2014) also. Despite the wide-ranging applications of these compounds, the crystal structure of this type of Meldrum's acids derivatives is poorly studied. A search of the Cambridge Structural Database (Groom & Allen, 2014) revealed only one aryl­methyl Meldrum's acid, namely 5-(2,3-di­meth­oxy­benzyl)-2,2-di­methyl-1,3-dioxane-4,6-dione (CSD refcode FONZOY; reference?), studied by a single-crystal X-ray diffraction. Only a few studies have been devoted to the determination of intra­molecular inter­actions into aryl­methyl Meldrum's acids. Anomalous deshielding in 1H NMR spectra were observed for the α-H atom in the di­carbonyl fragment for compounds containing different hydrogen-bond acceptors in the ortho-position of the benzene ring in comparison with derivatives of Meldrum's acids without a hydrogen-bond acceptor at the same position. The effect was even more pronounced when an additional substituent was introduced at the benzylic position. Moreover, in the crystalline state, strong intra­molecular hydrogen bonding was observed also (Fillion et al., 2009). The aim of this work was to gain more knowledge on the conformations, the intra- and mainly inter­molecular contacts (hydrogen bonds, van der Waals and ππ inter­actions) in 5-aryl­methyl-2,2-di­methyl-1,3-dioxane-4,6-diones in the crystalline state depending on different substituents. In order to find out whether these inter­actions in crystals of Meldrum's acid derivatives are general or unique, three structures of aryl­methyl Meldrum's acids were analyzed, namely 5-[4-(di­ethyl­amino)­benzyl]-2,2-di­methyl-1,3-dioxane-4,6-dione, (I), 2,2-di­methyl-5-(2,4,6-tri­meth­oxy­benzyl)-1,3-dioxane-4,6-dione, (II), 5-(4-hy­droxy-3,5-di­meth­oxy­benzyl)-2,2-di­methyl-1,3-dioxane-4,6-dione, (III).

Experimental top

1H (300 MHz) and 13C (75.5 MHz) NMR spectra were recorded on Bruker Avance 300 spectrometer; the samples were dissolved in CDCl3-d and the spectra were calibrated to the residue of CHCl3. IR spectra were recorded on Perkin–Elmer spectrometer (model: Spectrum BX, FT—IR system) for solid sample in KBr disc. Melting points were measured with a STUART melting point SMP10 apparatus and are uncorrected. Microanalysis was done with Carlo–Erba Instruments element analyzer (model: EA1108). High resolution mass spectra were recorded on Agilent 1290 Infinity series UPLC chromatograph equipped with Agilent 6230 TOF LC/MS mass spectrometer. Meldrum's acid, aromatic aldehydes, NaBH4, acetic acid and solvents were commercially available and were used without further purification.

Synthesis and crystallization top

\ Aryl­methyl Meldrum's acids (I)–(III) were synthesized according to a known method (Frost et al., 2009) with some modifications from Meldrum's acid (IV) and aromatic aldehyde, followed by reduction of the obtained 5-aryl­idene-1,3-dioxane-4,6-dione, (V)–(VII), with NaBH4 (see Scheme 1).

5-[(4-Hy­droxy-3,5-di­meth­oxy­phenyl)­methyl­ene]-2,2-di­methyl-1,3-dioxane-4,6-\ dione, (VII), is a known compound (Le et al., 2013) and was used without further purification.

General synthesis of 5-aryl­methyl-2,2-di­methyl-1,3-dioxane-4,6-diones (I)–(III) top

The syntheses were carried out according to a modification of the method of Frost et al. (2009). Aryl­idene Meldrum's acids (V)–(VII) (12 mmol) were dissolved in chloro­form (50 ml) and the solutions cooled to 270–273 K (ice bath), followed by addition of glacial acetic acid (5.7 ml). NaBH4 (0.53 g) was added portionwise after 5 min and the mixtures were further mixed for approximately 45 min until the colour of the solutions disappeared. The reactions were quenched with water (50 ml). The organic layers were separated and the water solutions extracted with chloro­form (50 ml). For each preparation, all chloro­form extracts were combined and washed with brine (2 × 75 ml) and water (2 × 75 ml). The chloro­form extracts were dried over Na2SO4, evaporated and recrystallized from ethanol. Single crystals of (I)–(III) suitable for X-ray analysis were obtained from solutions in methanol.

General synthesis of 5-aryl­idene-1,3-dioxane-4,6-diones (V)–(VII) top

The syntheses were carried out according to the previously described method of Bigi et al. (2001). In brief, 2,2-di­methyl-1,3-dioxane-4,6-dione, (IV) (1 g, 6.9 mmol), an aromatic aldehyde (6.9 mmol) and water (50 ml) were heated at 348 K for 2 h, followed with cooling to room temperature and filtration of the resulted precipitates. The solid material was air-dried in each case and recrystalized from ethanol.

Spectroscopic and analytical data top

5-[4-(Di­ethyl­amino)­benzyl]-2,2-di­methyl-1,3-dioxane-4,6-dione, (I) top

The compound appeared as white solid (yield 35%, m.p. 411-412 K). IR (KBr) ν (cm-1): 3690, 2995, 2940, 2900, 2450, 2360, 2340, 1675, 1605, 1565, 1515, 1475, 1385, 1365, 1345, 1295, 1255, 1210, 1195, 1110, 1100, 1035, 1020, 990, 960, 925, 825, 810, 795, 745, 730, 690, 645, 620, 550, 525, 520, 425; 1H NMR (300 MHz, CDCl3): δ 1.14 [6H, t, J = 7.1 Hz, N(CH2CH3)2], 1.45 (3H, s, Me), 1.73 (3H, s, Me), 3.3 [4H, q, J = 7.1 Hz, N(CH2CH3)2], 3.41 (2H, d, J = 4.7 Hz, CH2), 3.72 (1H, t, J = 4.7 Hz, CH), 6.61 (2H, d, J = 8.5 Hz, 2 × CArH), 7.17 (2H, d, J = 8.5 Hz, 2 × CArH); 13C NMR (75.5 MHz, CDCl3): δ 12.6 [N(CH2CH3)2], 27.5 (Me), 28.5 (Me), 31.7 (CH2), 44.4 [N(CH2CH3)2], 48.6 (CH), 105.2 (CMe2), 112.0 (2 × CArH), 123.6 (CArCH2), 130.9 (2 × CArH), 146.9 (CArNEt2), 165.8 (COOR). Analysis calculated for C17H23NO4: C 66.86, H 7.59, N 4.59%; found: C 66.53, H 7.70, N 4.38%.

2,2-Di­methyl-5-(2,4,6-tri­meth­oxy­benzyl)-1,3-dioxane-4,6-dione, (II) top

The compound appeared as white solid (yield 55%, m.p. 416–417 K). IR (KBr) ν (cm-1): 3680, 3010, 2980, 2950, 2910, 2865, 2840, 1780, 1750, 1610, 1600, 1505, 1465, 1420, 1395, 1390, 1375, 1335, 1265, 1235, 1215, 1205, 1155, 1120, 1085, 1075, 1035, 1025, 990, 955, 945, 925, 865, 835, 795, 750, 740, 705, 630, 545, 490, 420; 1H NMR (300 MHz, CDCl3): δ 1.75 (3H, s, Me), 1.82 (3H, s, Me), 3.37 (2H, d, J = 7.3 Hz, CH2), 3.79 (9H, s, 3 × OMe), 3.92 (1H, t, J = 7.3 Hz, CH), 6.12 (2H, s, 2 × CArH); 13C NMR (75.5 MHz, CDCl3): δ 22.8 (CH2), 27.7 (Me), 28.7 (Me), 45.0 (CH), 55.4 (OMe), 55.7 (2 × OMe), 90.7 (2 × CArH), 105.1 (CMe2/CArCH2), 105.2 (CMe2/CArCH2), 159.0 (2 × CArOMe), 160.4 (CArOMe), 165.8 (COOR). Analysis calculated for C16H20O7: C 59.22, H 6.22%; found: C 59.20, H 6.20%.

5-(4-hy­droxy-3,5-di­meth­oxy­benzyl)-2,2-di­methyl-1,3-dioxane-4,6-dione, (III) top

The compound appeared as white solid (yield 36%, m.p. 398 K). IR (KBr) ν (cm-1): 3560, 3500, 2995, 2955, 2940, 2875, 2840, 1785, 1750, 1615, 1520, 1460, 1420, 1995, 1385, 1350, 1310, 1265, 1245, 1215, 1195, 1115, 1055, 1020, 1000, 970, 950, 905, 885, 865, 850, 835, 810, 690, 670, 645, 635, 620, 585, 490, 455; 1H NMR (300 MHz, CDCl3): δ 1.47 (3H, s, Me), 1.72 (3H, s, Me), 3.42 (2H, d, J = 4.6 Hz, CH2), 3.72 (1H, t, J = 4.6 Hz, CH), 3.85 (6H, s, 2 × OMe), 5.48 (1H, brs, OH), 6.55 (2H, s, 2 × CArH); 13C NMR (75.5 MHz, CDCl3): δ 27.6 (Me), 28.7 (Me), 32.6 (CH2), 48.6 (CH), 56.5 (OMe), 105.4 (CMe2), 106.7 (2 × CArH), 128.2 (CArCH2), 133.9 (CArOH), 147.0 (2 × CArOMe), 165.7 (COOR). Analysis calculated for [M + Na]+ m/z: 333.0950; found m/z: 333.0942.

5-[(4-Di­ethyl­amino­phenyl)­methyl­ene]-2,2-di­methyl-1,3-dioxane-4,6-dione, (V) top

This compound is known [m.p. 398 K; literature 397–398 K (Strods et al., 1978)]. Nevertheless, NMR spectral data have not been provided previously. 1H NMR (300 MHz, CDCl3): δ 1.21 [6H, t, J = 7.1 Hz, N(CH2CH3)2], 1.75 (6H, s, 2 × Me), 3.46 [4H, q, J = 7.1 Hz, N(CH2CH3)2], 6.65 (2H, d, J = 9.3 Hz, 2 × CArH), 8.21 (2H, d, J = 9.3 Hz, 2 × CArH), 8.24 (1H, s, CH); 13C NMR (75.5 MHz, CDCl3): δ 12.7 [N(CH2CH3)2], 27.3 (2 × Me), 45.0 [N(CH2CH3)2], 103.4 (CMe2), 104.2 (CCH), 111.1 (2 × CArH), 119.8 (CArCH), 139.4 (2 × CArH), 152.8 (CArNEt2), 157.8 (CH), 161.6 (COOR), 165.4 (COOR).

5-[(2,4,6-trimetoxyphenyl)­methyl­ene]-2,2-di­methyl-1,3-dioxane-4,6-dione, (VI) top

The compound appeared as bright-yellow solid (yield 78%; m.p. 487 K). IR (KBr) ν (cm-1): 1750, 1725, 1595, 1570, 1495, 1470, 1450, 1395, 1385, 1365, 1335, 1285, 1230, 1205, 1190, 1155, 1140, 1110, 1030, 1005, 940, 905, 825, 785, 725, 490, 430; 1H NMR (300 MHz, CDCl3): δ 1.84 (6H, s, 2 × Me), 3.85 (6H, s, 2 × OMe), 3.88 (3H, s, OMe), 6.11 (2H, s, 2 × CArH), 8.49 (1H, s, CH); 13C NMR (75.5 MHz, CDCl3): δ 27.4 (2 × Me), 55.7 (OMe), 55.8 (2 × OMe), 90.8 (2 × CArH), 104.2 (CMe2), 106.1 (CArCH), 114.6 (CCH), 147.8 (CH), 161.1 (2 × CArOMe), 161.2 (CArOMe), 163.7 (COOR), 165.9 (COOR). Analysis calculated for [M + Na]+ m/z: 345.0945; found m/z: 345.0945.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

In (I), the position of the transferred H atom was located from a difference electron-density map and was refined in a least-squares full-matrix isotropic approximation.

Results and discussion top

The molecular structure of (I)–(III), with the atom-numbering schemes, are shown in Figs. 1, 2 and 3, respectively. The packing diagrams showing supra­molecular features of the structures are presented in Figs. 4, 5 and 6, respectively. In the crystal, 5-[4-(di­ethyl­amino)­benzyl]-2,2-di­methyl-1,3-dioxane-4,6-dione, (I), exists in the zwitterionic form. The sum of the valence angles at the C5 atom is 359.1 (3)°; thus it is in the sp2 hybridization state. An analysis of the bond lengths in the di­carbonyl fragment shows differentiation of single [C5—C6 = 1.411 (2) Å and C4—O2 = 1.252 (2) Å] and double bonds [C4—C5 = 1.384 (2) Å and C6—O19 = 1.229 (2) Å], suggesting the formation of the enolate structure. The absorption band in the IR spectrum at 1675 cm-1 is consistent with the existence of the enolate form. The H atom on O20 is transferred to atom N16 forming the zwitterionic structure of the residue. The heterocycle assumes a distorted boat conformation. Atoms C2 and C5 deviate from the least-squares plane [±0.006 (1) Å] calculated for the other four atoms in the heterocycle by 0.517 (2) and 0.074 (2) Å, respectively. The corresponding dihedral angles between the plane bottom of the boat and the triangles formed by atoms C2/O1/O3 and C4–C6 are 39.4 (2) and 6.1 (2)°, respectively. The total puckering amplitude for the heterocycle is 0.389 (2) Å. This is the first example where an anilinium-type zwitterionic form of Meldrum's acid is described and the inner ions are linked with the aryl­methyl moiety. Whereas, until now, the crystal structures of inner salts have been established only for di­methyl­amino­methyl Meldrum's acid (Li et al., 2005) and a pyridin-1-yl derivative of Meldrum's acid (Zia-Ebrahimi et al., 1994), where the distance between the ammonium ion and the deprotonated enalizated malonate moiety is remarkably shorter – just CH2 functionality. In the crystal, the residues are assembled by means of strong N—H···O hydrogen bonds into infinite chains with the graph set C(10) along the unit-cell a axis (Fig. 2).

As we have already mentioned in the Introduction, the ability of the acidic C—H bond to form an intra­molecular C—H···X (X = O, S, F) bonds in benzyl Meldrum's acids has been investigated by Fillion et al. (2009), and it was concluded that an intra­molecular C5—H···O hydrogen bond is able to drive the conformational properties of aryl­methyl Meldrum's acids in the solid state. In this respect, it was inter­esting to find out whether 2,2-di­methyl-5-(2,4,6-tri­meth­oxy­benzyl)-1,3-dioxane-4,6-dione, (II), which contains meth­oxy groups in both ortho-positions of the benzyl fragment, assumes the conformation with an intra­molecular C5—H···O hydrogen bond. It turned out that this kind of hydrogen bond is not present in the crystal structure of (II). In the molecule, the aryl­methyl fragment is rotated in the opposite direction to the acidic C5—H bond. The conformation of this type of Meldrum's acids is well described by the torsion angles H—C5—C7—C8 and C5—C7—C8—C9 (Table 2). The planar 2,4,6-tri­meth­oxy­phenyl fragment is almost perpendicular to the average plane of the six-membered heterocycle of the Meldrum's acid. The 1,3-dioxane moiety adopts a boat conformation. Atoms C2 and C5 deviate from the mean plane [±0.008 (1) Å] formed by the other four atoms in the heterocycle by 0.502 (2) and 0.383 (2) Å. The corresponding dihedral angles between the bottom of the boat and the triangles formed by atoms C2/O1/O3 and C4–C6 are 37.3 (1) and 27.2 (2)°, respectively. The puckering amplitude Q for the heterocycle is 0.515 (2) Å. Compound (II) has no classical hydrogen-bond donors and acceptors. Its packing in the crystal is governed, mainly, by van der Waals inter­actions. Two short contacts (Table 3) can be attributed to C—H···O type hydrogen bonds. Fig. 4 shows a fragment of the crystal packing for the structure of (II). Thus, one can conclude that the presence of a hydrogen-bond acceptor in the ortho-position of the aryl­methyl fragment does not guarantee the formation of a C5—H···O intra­molecular bond and the molecular conformation is dependent on the overall balance of the free energy of the crystal lattice.

The crystal structure of 5-(4-hy­droxy-3,5-di­meth­oxy­benzyl)-2,2-di­methyl-1,3-dioxane-4,6-dione, (III), contains two independent molecules (A and B) in the asymmetric unit. The molecules differ in their conformations defined, mainly, by the torsion angles along the C5—C7 and C7—C8 bonds (Table 2). The dihedral angles between the least-squares mean planes of the heterocycle and benzene rings in the molecules A and B are 41.8 (1) and 55.1 (1)°, respectively. In both molecules, the Meldrum's acid heterocycles assume the boat conformation. Atoms C2 and C5 deviate from the mean planes formed by the other four atoms of the rings in molecules A and B by 0.441 (2)/0.477 (2) and 0.476 (3)/0.469 (2) Å, respectively. The corresponding dihedral angles between the bottom of the boat and the triangles formed by atoms C2/O1/O3 and C4–C6 for molecules A and B are 32.3 (2)/33.4 (2) and 35.0 (2)/33.5 (2)°, respectively. The corresponding values of the puckering amplitude Q for the heterocycle in molecules A and B are 0.533 (2) and 0.546 (2) Å, respectively. Molecules A and B form dimers by means of hydrogen bonds of the O—H···O type (Table 3). The dimers are associated into a tetra­meric synthon through ππ inter­actions of the partially overlapping aryl rings of molecules A and B (Fig. 6). The distance between the centroids is 3.678 Å. The hy­droxy groups are also involved in intra­molecular hydrogen bonds with the O atoms of adjacent meth­oxy groups. There are also intra­molecular C—H···O inter­actions in the structure. Their geometrical parameters are given in the Table 3.

Despite the high structural similarity of studied aryl­methyl Meldrum's acids, the nature of different substituents resulted in remarkable differences in both the molecular conformations and the crystal packing arrangements. The presence of a substituent with a basic centre in compound (I) leads to the formation of an inner salt accompanied by drastic changes in the conformation of the 1,3-dioxane-4,6-dione fragment. By virtue of strong hydrogen bonds of the N—H···O type, the residues are assembled into infinite chains with the graph-set C(10). Compound (II) contains meth­oxy groups in both the ortho- and para-positions of the aryl­methyl fragment. Hypothetically, one could expect the formation of an intra­molecular C5—H···O hydrogen bond. However, in the crystal, this hydrogen bond was not observed. Because of the absence of classical hydrogen-bond donors in this structure, the crystal packing is controled by the van der Waals forces and weak C—H···O inter­actions. Compound (III) contains meth­oxy groups in both meta-positions and a hy­droxy group in the para-position. The substituted aryl moiety forms an extensive conjugated π-electron system that can give rise to the emergence of ππ inter­actions in the crystal packing. Indeed, in the structure of (III), we observed the formation of supra­molecular tetra­meric synthons which comprise hydrogen-bonded dimers associated into tetra­mers through ππ inter­actions of overlapping benzene rings.

Computing details top

For all compounds, data collection: COLLECT (Bruker, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The molecular structure of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 3] Fig. 3. The molecular structure of (III), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 4] Fig. 4. A fragment of the crystal packing for (I), showing N—H···O hydrogen-bonded chains with the graph-set descriptor C(10).
[Figure 5] Fig. 5. A fragment of the crystal packing for (II), showing the C—H···O hydrogen bonding (dashed lines).
[Figure 6] Fig. 6. A fragment of the crystal packing for (III), showing tetrameric synthon formed by O—H···O hydrogen bonds and ππ interactions.
(I) 5-[4-(Diethylamino)benzyl]-2,2-dimethyl-1,3-dioxane-4,6-dione top
Crystal data top
C17H23NO4F(000) = 1312
Mr = 305.36Dx = 1.224 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 41560 reflections
a = 15.0721 (4) Åθ = 1.0–27.1°
b = 11.3109 (3) ŵ = 0.09 mm1
c = 19.4443 (4) ÅT = 190 K
V = 3314.85 (14) Å3Block, colourless
Z = 80.42 × 0.25 × 0.18 mm
Data collection top
Nonius KappaCCD
diffractometer
2532 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 27.0°, θmin = 2.5°
CCD scansh = 1919
6647 measured reflectionsk = 1414
3586 independent reflectionsl = 2424
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0749P)2 + 0.3201P]
where P = (Fo2 + 2Fc2)/3
3586 reflections(Δ/σ)max = 0.004
207 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C17H23NO4V = 3314.85 (14) Å3
Mr = 305.36Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 15.0721 (4) ŵ = 0.09 mm1
b = 11.3109 (3) ÅT = 190 K
c = 19.4443 (4) Å0.42 × 0.25 × 0.18 mm
Data collection top
Nonius KappaCCD
diffractometer
2532 reflections with I > 2σ(I)
6647 measured reflectionsRint = 0.036
3586 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.42 e Å3
3586 reflectionsΔρmin = 0.32 e Å3
207 parameters
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
O190.39182 (8)0.89445 (11)0.25622 (6)0.0368 (3)
O30.22071 (7)0.89290 (11)0.10008 (6)0.0304 (3)
N160.70440 (9)0.52977 (13)0.07922 (7)0.0298 (3)
O10.25444 (7)0.87494 (11)0.21756 (5)0.0326 (3)
O200.32271 (7)0.93560 (12)0.02228 (6)0.0342 (3)
C80.52464 (9)0.81687 (14)0.10696 (8)0.0235 (4)
C100.63975 (10)0.71860 (15)0.04146 (8)0.0283 (4)
H20.67810.71760.00400.034*
C90.58260 (10)0.81321 (15)0.05149 (8)0.0271 (4)
H30.58310.87560.02030.033*
C130.52375 (10)0.71987 (15)0.15134 (8)0.0275 (4)
H40.48390.71920.18790.033*
C60.34447 (11)0.88844 (14)0.20485 (8)0.0265 (4)
C40.30898 (10)0.90911 (14)0.08390 (8)0.0254 (4)
C170.76788 (11)0.52129 (17)0.13946 (9)0.0370 (4)
H7A0.80900.45690.13130.044*
H7B0.73450.50270.18070.044*
C70.46781 (10)0.92404 (15)0.12018 (8)0.0269 (4)
H8A0.49300.96730.15860.032*
H8B0.47090.97500.08010.032*
C50.37157 (10)0.89992 (13)0.13570 (7)0.0233 (3)
C120.58020 (10)0.62493 (15)0.14266 (8)0.0285 (4)
H100.57880.56140.17300.034*
C110.63914 (10)0.62607 (14)0.08772 (8)0.0263 (4)
C20.20050 (11)0.83192 (17)0.16270 (9)0.0345 (4)
C150.66273 (13)0.41035 (17)0.06799 (11)0.0439 (5)
H13A0.62460.39190.10680.053*
H13B0.70910.35090.06610.053*
C180.81919 (13)0.63211 (19)0.15121 (10)0.0455 (5)
H14A0.77920.69490.16310.068*
H14B0.86070.62010.18800.068*
H14C0.85080.65270.11000.068*
C210.21448 (15)0.70056 (19)0.15389 (10)0.0498 (5)
H15A0.19850.66050.19560.075*
H15B0.17810.67230.11690.075*
H15C0.27570.68540.14360.075*
C220.10625 (12)0.8645 (2)0.18035 (11)0.0553 (6)
H16A0.10140.94880.18440.083*
H16B0.06730.83710.14470.083*
H16C0.09000.82830.22320.083*
C140.60972 (16)0.4049 (2)0.00370 (14)0.0656 (7)
H17A0.64580.42930.03440.098*
H17B0.58970.32530.00360.098*
H17C0.55940.45650.00760.098*
HN160.7422 (14)0.548 (2)0.0384 (10)0.051 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O190.0388 (7)0.0469 (8)0.0247 (6)0.0034 (6)0.0066 (5)0.0072 (5)
O30.0221 (6)0.0414 (7)0.0277 (6)0.0028 (5)0.0011 (5)0.0019 (5)
N160.0285 (7)0.0276 (8)0.0332 (8)0.0021 (6)0.0092 (6)0.0010 (6)
O10.0293 (6)0.0439 (8)0.0248 (6)0.0008 (5)0.0034 (5)0.0052 (5)
O200.0293 (6)0.0499 (8)0.0235 (6)0.0060 (6)0.0032 (5)0.0070 (5)
C80.0190 (7)0.0263 (9)0.0250 (8)0.0029 (6)0.0038 (6)0.0016 (6)
C100.0272 (8)0.0332 (10)0.0244 (8)0.0030 (7)0.0047 (6)0.0014 (7)
C90.0267 (8)0.0292 (9)0.0253 (8)0.0044 (7)0.0020 (7)0.0026 (7)
C130.0231 (8)0.0348 (10)0.0247 (8)0.0015 (7)0.0040 (6)0.0005 (7)
C60.0302 (8)0.0230 (9)0.0264 (8)0.0034 (7)0.0004 (7)0.0044 (7)
C40.0226 (8)0.0256 (9)0.0280 (8)0.0011 (7)0.0009 (6)0.0013 (7)
C170.0364 (10)0.0431 (11)0.0316 (9)0.0167 (8)0.0078 (8)0.0109 (8)
C70.0250 (8)0.0266 (9)0.0292 (8)0.0017 (7)0.0043 (7)0.0003 (7)
C50.0239 (8)0.0206 (8)0.0253 (8)0.0021 (6)0.0007 (6)0.0016 (6)
C120.0270 (8)0.0299 (9)0.0288 (8)0.0026 (7)0.0027 (7)0.0054 (7)
C110.0231 (8)0.0275 (9)0.0283 (8)0.0014 (7)0.0011 (6)0.0019 (7)
C20.0313 (9)0.0445 (11)0.0278 (9)0.0078 (8)0.0018 (7)0.0002 (8)
C150.0406 (10)0.0325 (11)0.0585 (12)0.0018 (8)0.0150 (9)0.0060 (9)
C180.0428 (11)0.0549 (13)0.0389 (10)0.0079 (10)0.0086 (9)0.0006 (9)
C210.0640 (13)0.0414 (12)0.0441 (11)0.0172 (10)0.0016 (10)0.0007 (9)
C220.0313 (10)0.0883 (19)0.0465 (12)0.0063 (11)0.0073 (9)0.0032 (11)
C140.0586 (13)0.0534 (15)0.0848 (17)0.0049 (11)0.0067 (13)0.0183 (13)
Geometric parameters (Å, º) top
O19—C61.229 (2)C17—H7B0.9700
O3—C41.3794 (18)C7—C51.506 (2)
O3—C21.432 (2)C7—H8A0.9700
N16—C111.477 (2)C7—H8B0.9700
N16—C151.505 (2)C12—C111.389 (2)
N16—C171.515 (2)C12—H100.9300
N16—HN161.00 (2)C2—C221.507 (3)
O1—C61.388 (2)C2—C211.510 (3)
O1—C21.427 (2)C15—C141.485 (3)
O20—C41.252 (2)C15—H13A0.9700
C8—C91.388 (2)C15—H13B0.9700
C8—C131.396 (2)C18—H14A0.9600
C8—C71.506 (2)C18—H14B0.9600
C10—C111.380 (2)C18—H14C0.9600
C10—C91.387 (2)C21—H15A0.9600
C10—H20.9300C21—H15B0.9600
C9—H30.9300C21—H15C0.9600
C13—C121.380 (2)C22—H16A0.9600
C13—H40.9300C22—H16B0.9600
C6—C51.411 (2)C22—H16C0.9600
C4—C51.384 (2)C14—H17A0.9600
C17—C181.491 (3)C14—H17B0.9600
C17—H7A0.9700C14—H17C0.9600
C4—O3—C2117.59 (12)C13—C12—H10120.6
C11—N16—C15113.58 (13)C11—C12—H10120.6
C11—N16—C17112.37 (13)C10—C11—C12120.82 (15)
C15—N16—C17108.58 (14)C10—C11—N16118.81 (14)
C11—N16—HN16108.2 (13)C12—C11—N16120.34 (14)
C15—N16—HN16108.2 (13)O1—C2—O3110.50 (13)
C17—N16—HN16105.5 (12)O1—C2—C22106.47 (15)
C6—O1—C2117.49 (12)O3—C2—C22106.04 (15)
C9—C8—C13117.57 (15)O1—C2—C21109.92 (15)
C9—C8—C7120.95 (14)O3—C2—C21110.34 (14)
C13—C8—C7121.43 (14)C22—C2—C21113.44 (17)
C11—C10—C9119.29 (14)C14—C15—N16112.59 (17)
C11—C10—H2120.4C14—C15—H13A109.1
C9—C10—H2120.4N16—C15—H13A109.1
C10—C9—C8121.52 (15)C14—C15—H13B109.1
C10—C9—H3119.2N16—C15—H13B109.1
C8—C9—H3119.2H13A—C15—H13B107.8
C12—C13—C8122.00 (14)C17—C18—H14A109.5
C12—C13—H4119.0C17—C18—H14B109.5
C8—C13—H4119.0H14A—C18—H14B109.5
O19—C6—O1115.41 (14)C17—C18—H14C109.5
O19—C6—C5126.94 (15)H14A—C18—H14C109.5
O1—C6—C5117.56 (14)H14B—C18—H14C109.5
O20—C4—O3114.16 (13)C2—C21—H15A109.5
O20—C4—C5127.00 (14)C2—C21—H15B109.5
O3—C4—C5118.78 (14)H15A—C21—H15B109.5
C18—C17—N16113.13 (14)C2—C21—H15C109.5
C18—C17—H7A109.0H15A—C21—H15C109.5
N16—C17—H7A109.0H15B—C21—H15C109.5
C18—C17—H7B109.0C2—C22—H16A109.5
N16—C17—H7B109.0C2—C22—H16B109.5
H7A—C17—H7B107.8H16A—C22—H16B109.5
C8—C7—C5115.84 (13)C2—C22—H16C109.5
C8—C7—H8A108.3H16A—C22—H16C109.5
C5—C7—H8A108.3H16B—C22—H16C109.5
C8—C7—H8B108.3C15—C14—H17A109.5
C5—C7—H8B108.3C15—C14—H17B109.5
H8A—C7—H8B107.4H17A—C14—H17B109.5
C4—C5—C6120.20 (14)C15—C14—H17C109.5
C4—C5—C7119.80 (14)H17A—C14—H17C109.5
C6—C5—C7119.09 (13)H17B—C14—H17C109.5
C13—C12—C11118.75 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H8A···O190.972.572.9019100
C7—H8B···O200.972.542.9023102
N16—HN16···O20i1.00 (2)1.70 (2)2.688 (2)169 (2)
C10—H2···O3i0.932.463.264 (2)144
C17—H7B···O1ii0.972.463.253 (2)139
C17—H7B···O19ii0.972.573.459 (2)152
C12—H10···O19ii0.932.383.292 (2)168
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x1, y1/2, z+1/2.
(II) 2,2-Dimethyl-5-(2,4,6-trimethoxybenzyl)-1,3-dioxane-4,6-dione top
Crystal data top
C16H20O7F(000) = 1376
Mr = 324.32Dx = 1.438 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 15283 reflections
a = 9.8128 (2) Åθ = 1.0–27.5°
b = 10.0235 (2) ŵ = 0.11 mm1
c = 30.4669 (6) ÅT = 190 K
V = 2996.68 (10) Å3Plate, colourless
Z = 80.26 × 0.24 × 0.10 mm
Data collection top
Nonius KappaCCD
diffractometer
2421 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 27.4°, θmin = 2.5°
CCD scansh = 1212
6059 measured reflectionsk = 1212
3374 independent reflectionsl = 3939
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0465P)2 + 0.7724P]
where P = (Fo2 + 2Fc2)/3
3374 reflections(Δ/σ)max = 0.009
213 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C16H20O7V = 2996.68 (10) Å3
Mr = 324.32Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 9.8128 (2) ŵ = 0.11 mm1
b = 10.0235 (2) ÅT = 190 K
c = 30.4669 (6) Å0.26 × 0.24 × 0.10 mm
Data collection top
Nonius KappaCCD
diffractometer
2421 reflections with I > 2σ(I)
6059 measured reflectionsRint = 0.040
3374 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.00Δρmax = 0.27 e Å3
3374 reflectionsΔρmin = 0.24 e Å3
213 parameters
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
O30.70620 (11)0.09851 (11)0.07913 (4)0.0200 (3)
O10.63264 (10)0.08643 (11)0.03698 (3)0.0208 (3)
O150.36539 (11)0.25988 (11)0.21152 (4)0.0219 (3)
O200.50007 (11)0.23932 (11)0.06669 (4)0.0230 (3)
O210.65142 (12)0.11714 (12)0.14892 (4)0.0264 (3)
O170.03063 (10)0.01509 (12)0.16158 (4)0.0246 (3)
O190.40355 (10)0.04681 (11)0.09580 (4)0.0223 (3)
C50.62662 (15)0.10193 (16)0.11675 (5)0.0178 (3)
H10.71350.14760.12190.021*
C140.28290 (17)0.34188 (17)0.23906 (6)0.0248 (4)
H2A0.22140.39320.22130.037*
H2B0.34010.40100.25560.037*
H2C0.23160.28660.25880.037*
C90.32122 (15)0.01330 (15)0.12661 (5)0.0181 (3)
C110.10456 (15)0.05114 (16)0.16010 (5)0.0196 (4)
C60.57935 (15)0.14942 (16)0.07239 (5)0.0181 (3)
C120.16063 (16)0.14689 (16)0.18732 (5)0.0202 (4)
H60.10680.19320.20730.024*
C100.18333 (15)0.01686 (15)0.12965 (5)0.0190 (4)
H70.14460.08140.11160.023*
C220.87603 (16)0.05431 (17)0.04927 (6)0.0247 (4)
H8A0.87270.10990.07490.037*
H8B0.89730.10790.02410.037*
H8C0.94500.01270.05300.037*
C40.66056 (15)0.04586 (16)0.11732 (5)0.0187 (3)
C70.53346 (15)0.14686 (17)0.15413 (5)0.0207 (4)
H10A0.57230.11350.18130.025*
H10B0.53780.24340.15550.025*
C230.73435 (18)0.09981 (17)0.00263 (5)0.0265 (4)
H11A0.79910.17100.00580.040*
H11B0.75660.04790.02290.040*
H11C0.64450.13650.00060.040*
C180.35868 (17)0.16978 (16)0.07704 (6)0.0236 (4)
H12A0.33850.23220.10010.035*
H12B0.42920.20540.05860.035*
H12C0.27820.15440.05990.035*
C20.73884 (15)0.01231 (16)0.04268 (5)0.0199 (4)
C80.38392 (15)0.10803 (16)0.15365 (5)0.0175 (3)
C160.10763 (16)0.06787 (18)0.19715 (6)0.0267 (4)
H15A0.06270.04740.22430.040*
H15B0.19700.02890.19710.040*
H15C0.11520.16290.19400.040*
C130.29995 (15)0.17235 (15)0.18408 (5)0.0184 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0245 (6)0.0159 (6)0.0196 (6)0.0020 (5)0.0024 (5)0.0005 (5)
O10.0229 (6)0.0206 (6)0.0189 (6)0.0049 (4)0.0004 (5)0.0003 (5)
O150.0239 (6)0.0207 (6)0.0212 (6)0.0012 (5)0.0019 (5)0.0073 (5)
O200.0212 (6)0.0181 (6)0.0298 (7)0.0038 (5)0.0009 (5)0.0007 (5)
O210.0319 (7)0.0243 (7)0.0228 (7)0.0006 (5)0.0010 (5)0.0057 (5)
O170.0175 (6)0.0285 (7)0.0277 (7)0.0019 (5)0.0049 (5)0.0045 (5)
O190.0204 (6)0.0215 (6)0.0251 (7)0.0034 (5)0.0041 (5)0.0102 (5)
C50.0152 (7)0.0184 (8)0.0199 (8)0.0018 (6)0.0006 (6)0.0026 (7)
C140.0315 (9)0.0210 (9)0.0220 (9)0.0001 (8)0.0039 (7)0.0059 (7)
C90.0210 (8)0.0161 (8)0.0173 (9)0.0015 (6)0.0025 (6)0.0003 (7)
C110.0171 (8)0.0186 (8)0.0231 (9)0.0011 (6)0.0004 (6)0.0032 (7)
C60.0167 (7)0.0160 (8)0.0216 (9)0.0043 (6)0.0020 (6)0.0012 (7)
C120.0221 (8)0.0183 (8)0.0202 (9)0.0016 (7)0.0051 (7)0.0013 (7)
C100.0206 (8)0.0165 (8)0.0199 (9)0.0008 (6)0.0010 (6)0.0014 (7)
C220.0230 (8)0.0223 (9)0.0287 (10)0.0020 (7)0.0057 (7)0.0013 (8)
C40.0158 (7)0.0217 (8)0.0185 (8)0.0017 (7)0.0015 (6)0.0000 (7)
C70.0190 (8)0.0221 (9)0.0210 (9)0.0015 (7)0.0003 (6)0.0048 (7)
C230.0346 (9)0.0222 (9)0.0226 (9)0.0047 (7)0.0014 (7)0.0014 (8)
C180.0294 (9)0.0169 (8)0.0244 (9)0.0024 (7)0.0028 (7)0.0045 (7)
C20.0224 (8)0.0167 (8)0.0206 (9)0.0044 (6)0.0037 (7)0.0034 (7)
C80.0190 (8)0.0164 (8)0.0171 (8)0.0004 (6)0.0012 (6)0.0010 (7)
C160.0207 (8)0.0340 (10)0.0256 (10)0.0002 (7)0.0057 (7)0.0006 (8)
C130.0231 (8)0.0140 (8)0.0180 (8)0.0001 (6)0.0020 (6)0.0005 (7)
Geometric parameters (Å, º) top
O3—C41.3539 (19)C11—C101.386 (2)
O3—C21.4430 (18)C12—C131.394 (2)
O1—C61.3551 (18)C12—H60.9300
O1—C21.4477 (18)C10—H70.9300
O15—C131.3714 (18)C22—C21.516 (2)
O15—C141.4265 (18)C22—H8A0.9600
O20—C61.2032 (18)C22—H8B0.9600
O21—C41.2022 (18)C22—H8C0.9600
O17—C111.3757 (19)C7—C81.518 (2)
O17—C161.4231 (19)C7—H10A0.9700
O19—C91.3773 (18)C7—H10B0.9700
O19—C181.4282 (18)C23—C21.503 (2)
C5—C61.506 (2)C23—H11A0.9600
C5—C41.518 (2)C23—H11B0.9600
C5—C71.528 (2)C23—H11C0.9600
C5—H10.9800C18—H12A0.9600
C14—H2A0.9600C18—H12B0.9600
C14—H2B0.9600C18—H12C0.9600
C14—H2C0.9600C8—C131.398 (2)
C9—C101.390 (2)C16—H15A0.9600
C9—C81.400 (2)C16—H15B0.9600
C11—C121.383 (2)C16—H15C0.9600
C4—O3—C2120.09 (12)O21—C4—C5124.94 (15)
C6—O1—C2120.05 (12)O3—C4—C5116.29 (13)
C13—O15—C14117.48 (12)C8—C7—C5119.70 (13)
C11—O17—C16116.07 (12)C8—C7—H10A107.4
C9—O19—C18118.00 (12)C5—C7—H10A107.4
C6—C5—C4112.72 (13)C8—C7—H10B107.4
C6—C5—C7113.04 (13)C5—C7—H10B107.4
C4—C5—C7114.21 (13)H10A—C7—H10B106.9
C6—C5—H1105.3C2—C23—H11A109.5
C4—C5—H1105.3C2—C23—H11B109.5
C7—C5—H1105.3H11A—C23—H11B109.5
O15—C14—H2A109.5C2—C23—H11C109.5
O15—C14—H2B109.5H11A—C23—H11C109.5
H2A—C14—H2B109.5H11B—C23—H11C109.5
O15—C14—H2C109.5O19—C18—H12A109.5
H2A—C14—H2C109.5O19—C18—H12B109.5
H2B—C14—H2C109.5H12A—C18—H12B109.5
O19—C9—C10121.43 (14)O19—C18—H12C109.5
O19—C9—C8116.11 (13)H12A—C18—H12C109.5
C10—C9—C8122.43 (14)H12B—C18—H12C109.5
O17—C11—C12123.12 (14)O3—C2—O1110.00 (11)
O17—C11—C10115.50 (14)O3—C2—C23105.59 (13)
C12—C11—C10121.38 (14)O1—C2—C23106.28 (12)
O20—C6—O1118.91 (14)O3—C2—C22111.04 (13)
O20—C6—C5124.44 (14)O1—C2—C22110.73 (13)
O1—C6—C5116.64 (13)C23—C2—C22112.98 (13)
C11—C12—C13118.34 (15)C13—C8—C9116.37 (14)
C11—C12—H6120.8C13—C8—C7116.43 (14)
C13—C12—H6120.8C9—C8—C7127.18 (14)
C11—C10—C9118.72 (15)O17—C16—H15A109.5
C11—C10—H7120.6O17—C16—H15B109.5
C9—C10—H7120.6H15A—C16—H15B109.5
C2—C22—H8A109.5O17—C16—H15C109.5
C2—C22—H8B109.5H15A—C16—H15C109.5
H8A—C22—H8B109.5H15B—C16—H15C109.5
C2—C22—H8C109.5O15—C13—C12122.21 (14)
H8A—C22—H8C109.5O15—C13—C8115.04 (13)
H8B—C22—H8C109.5C12—C13—C8122.72 (15)
O21—C4—O3118.76 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H8C···O20i0.962.583.425 (2)147
C16—H15B···O21ii0.962.553.345 (2)140
Symmetry codes: (i) x+3/2, y1/2, z; (ii) x1, y, z.
(III) 5-(4-Hydroxy-3,5-dimethoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione top
Crystal data top
C15H18O7F(000) = 2624
Mr = 310.29Dx = 1.408 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 22.9942 (5) ÅCell parameters from 14754 reflections
b = 10.1840 (2) Åθ = 1.0–27.5°
c = 26.9904 (7) ŵ = 0.11 mm1
β = 112.125 (1)°T = 190 K
V = 5855.0 (2) Å3Block, colourless
Z = 160.32 × 0.14 × 0.10 mm
Data collection top
Nonius KappaCCD
diffractometer
3333 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
Graphite monochromatorθmax = 27.5°, θmin = 4.1°
CCD scansh = 2929
11293 measured reflectionsk = 1312
6610 independent reflectionsl = 3534
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0491P)2]
where P = (Fo2 + 2Fc2)/3
6610 reflections(Δ/σ)max < 0.001
407 parametersΔρmax = 0.26 e Å3
1 restraintΔρmin = 0.28 e Å3
Crystal data top
C15H18O7V = 5855.0 (2) Å3
Mr = 310.29Z = 16
Monoclinic, C2/cMo Kα radiation
a = 22.9942 (5) ŵ = 0.11 mm1
b = 10.1840 (2) ÅT = 190 K
c = 26.9904 (7) Å0.32 × 0.14 × 0.10 mm
β = 112.125 (1)°
Data collection top
Nonius KappaCCD
diffractometer
3333 reflections with I > 2σ(I)
11293 measured reflectionsRint = 0.071
6610 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0561 restraint
wR(F2) = 0.128H-atom parameters constrained
S = 0.96Δρmax = 0.26 e Å3
6610 reflectionsΔρmin = 0.28 e Å3
407 parameters
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
O19A0.68746 (7)0.22214 (15)0.00532 (6)0.0288 (4)
O3A0.75965 (7)0.57215 (14)0.01900 (6)0.0285 (4)
O16A0.64076 (8)0.02557 (15)0.22066 (7)0.0310 (4)
H16A0.64850.05760.25030.046*
O1B0.44928 (7)0.16261 (16)0.18401 (7)0.0315 (4)
O16B0.65988 (7)0.51559 (16)0.13938 (7)0.0313 (4)
H16B0.68290.53620.16980.047*
O17A0.73529 (7)0.18461 (15)0.27644 (7)0.0335 (4)
O15B0.58398 (7)0.40497 (15)0.04951 (6)0.0313 (4)
O3B0.47010 (7)0.16576 (16)0.10492 (6)0.0323 (4)
O15A0.61118 (7)0.02194 (15)0.11918 (6)0.0302 (4)
O17B0.64798 (8)0.47330 (16)0.23247 (7)0.0347 (4)
O1A0.67768 (7)0.42422 (15)0.02468 (6)0.0284 (4)
O20B0.45815 (8)0.01801 (16)0.05925 (7)0.0372 (5)
C11A0.67329 (10)0.0924 (2)0.19515 (10)0.0231 (6)
O19B0.42579 (8)0.02352 (18)0.21338 (7)0.0398 (5)
C9A0.75431 (10)0.2423 (2)0.19489 (10)0.0247 (6)
H20.78640.30070.21300.030*
O20A0.83454 (8)0.51768 (17)0.09498 (7)0.0448 (5)
C8A0.73847 (10)0.2205 (2)0.14057 (10)0.0229 (6)
C10B0.60468 (10)0.4106 (2)0.18890 (10)0.0246 (6)
C12A0.65821 (10)0.0684 (2)0.14124 (10)0.0222 (6)
C6B0.44930 (11)0.0293 (3)0.18611 (10)0.0284 (6)
C7B0.46316 (10)0.1855 (2)0.14484 (10)0.0304 (6)
H7A0.42730.19550.11150.037*
H7B0.45060.21480.17350.037*
C4B0.46868 (10)0.0324 (2)0.10159 (10)0.0271 (6)
C7A0.77508 (10)0.2871 (2)0.11156 (10)0.0279 (6)
H9A0.79020.22010.09380.033*
H9B0.81160.32870.13800.033*
C18A0.77638 (11)0.2876 (2)0.30543 (10)0.0355 (7)
H10A0.81740.27370.30480.053*
H10B0.77900.28750.34180.053*
H10C0.76030.37050.28920.053*
C11B0.61265 (10)0.4346 (2)0.14147 (10)0.0250 (6)
C13B0.52368 (10)0.2968 (2)0.09572 (10)0.0268 (6)
H120.49640.25830.06430.032*
C13A0.69063 (10)0.1314 (2)0.11425 (10)0.0233 (6)
H130.68050.11440.07810.028*
C6A0.70026 (10)0.3358 (2)0.01592 (10)0.0236 (6)
C10A0.72232 (10)0.1770 (2)0.22221 (9)0.0237 (6)
C12B0.57198 (10)0.3768 (2)0.09423 (10)0.0245 (6)
C5A0.73943 (10)0.3910 (2)0.06974 (9)0.0223 (6)
H170.71040.43460.08330.027*
C9B0.55630 (10)0.3305 (2)0.19025 (10)0.0291 (6)
H180.55130.31520.22240.035*
C22A0.69361 (12)0.6065 (2)0.07065 (10)0.0370 (7)
H19A0.70440.69790.06860.055*
H19B0.65210.59410.09700.055*
H19C0.72310.55670.08050.055*
C2B0.48196 (11)0.2303 (2)0.15522 (10)0.0288 (6)
C14B0.54495 (11)0.3423 (3)0.00071 (10)0.0386 (7)
H21A0.54810.24870.00530.058*
H21B0.55850.36720.02750.058*
H21C0.50210.36900.00830.058*
C8B0.51559 (10)0.2736 (2)0.14324 (10)0.0255 (6)
C22B0.45127 (12)0.3631 (2)0.14144 (11)0.0409 (7)
H23A0.40760.35240.11980.061*
H23B0.45550.40880.17370.061*
H23C0.47120.41290.12200.061*
C21B0.55136 (10)0.2401 (2)0.18788 (11)0.0357 (7)
H24A0.57120.29060.16860.054*
H24B0.55780.28230.22130.054*
H24C0.56930.15370.19450.054*
C2A0.69550 (10)0.5607 (2)0.01715 (10)0.0259 (6)
C5B0.48038 (10)0.0394 (2)0.15315 (9)0.0230 (6)
H260.52570.03530.17370.028*
C4A0.78254 (11)0.4965 (2)0.06355 (10)0.0276 (6)
C21A0.65274 (11)0.6377 (2)0.00289 (11)0.0376 (7)
H28A0.65650.60490.03730.056*
H28B0.61010.62850.02180.056*
H28C0.66440.72870.00590.056*
C14A0.59698 (12)0.0571 (3)0.06491 (11)0.0434 (7)
H29A0.58240.01890.04260.065*
H29B0.56490.12330.05440.065*
H29C0.63400.09080.06100.065*
C18B0.64126 (13)0.4580 (3)0.28239 (11)0.0458 (8)
H30A0.60100.49060.27960.069*
H30B0.67370.50630.30940.069*
H30C0.64460.36670.29190.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O19A0.0338 (10)0.0249 (10)0.0303 (11)0.0059 (8)0.0152 (8)0.0009 (8)
O3A0.0253 (9)0.0283 (9)0.0279 (10)0.0059 (7)0.0055 (8)0.0058 (8)
O16A0.0363 (10)0.0367 (10)0.0249 (10)0.0101 (8)0.0172 (9)0.0030 (8)
O1B0.0302 (9)0.0383 (11)0.0291 (11)0.0053 (8)0.0149 (8)0.0068 (8)
O16B0.0340 (10)0.0326 (10)0.0283 (10)0.0091 (8)0.0127 (8)0.0054 (9)
O17A0.0412 (10)0.0353 (10)0.0233 (10)0.0132 (8)0.0115 (8)0.0067 (8)
O15B0.0323 (9)0.0390 (10)0.0229 (10)0.0101 (8)0.0109 (8)0.0028 (8)
O3B0.0408 (10)0.0340 (11)0.0218 (10)0.0076 (8)0.0113 (8)0.0026 (8)
O15A0.0330 (9)0.0346 (10)0.0226 (10)0.0142 (8)0.0101 (8)0.0043 (8)
O17B0.0403 (10)0.0402 (10)0.0245 (11)0.0089 (8)0.0133 (9)0.0066 (8)
O1A0.0295 (9)0.0235 (9)0.0277 (10)0.0032 (7)0.0056 (8)0.0019 (8)
O20B0.0458 (11)0.0442 (11)0.0221 (11)0.0051 (9)0.0134 (9)0.0038 (9)
C11A0.0231 (13)0.0219 (13)0.0279 (15)0.0012 (10)0.0138 (11)0.0044 (11)
O19B0.0414 (11)0.0568 (12)0.0301 (11)0.0046 (9)0.0234 (9)0.0034 (9)
C9A0.0221 (12)0.0220 (14)0.0279 (16)0.0034 (10)0.0069 (12)0.0010 (11)
O20A0.0315 (10)0.0488 (12)0.0400 (12)0.0185 (9)0.0029 (9)0.0093 (9)
C8A0.0183 (12)0.0232 (13)0.0252 (15)0.0019 (10)0.0060 (11)0.0065 (11)
C10B0.0261 (13)0.0238 (14)0.0232 (15)0.0018 (11)0.0084 (11)0.0057 (12)
C12A0.0218 (12)0.0226 (13)0.0213 (14)0.0016 (10)0.0071 (11)0.0022 (11)
C6B0.0214 (13)0.0446 (18)0.0181 (15)0.0027 (12)0.0062 (11)0.0035 (13)
C7B0.0258 (13)0.0386 (16)0.0304 (16)0.0003 (12)0.0147 (12)0.0010 (13)
C4B0.0241 (13)0.0328 (16)0.0253 (16)0.0036 (11)0.0104 (12)0.0005 (12)
C7A0.0203 (12)0.0324 (14)0.0297 (15)0.0004 (11)0.0080 (11)0.0060 (12)
C18A0.0402 (15)0.0340 (15)0.0276 (16)0.0069 (12)0.0073 (13)0.0088 (12)
C11B0.0229 (13)0.0230 (13)0.0307 (16)0.0006 (11)0.0118 (12)0.0013 (12)
C13B0.0252 (13)0.0271 (14)0.0262 (15)0.0014 (11)0.0077 (11)0.0037 (11)
C13A0.0266 (13)0.0265 (13)0.0192 (14)0.0033 (11)0.0113 (11)0.0028 (11)
C6A0.0193 (12)0.0285 (15)0.0269 (15)0.0009 (11)0.0132 (11)0.0016 (12)
C10A0.0257 (13)0.0254 (14)0.0192 (14)0.0020 (11)0.0075 (11)0.0011 (11)
C12B0.0285 (13)0.0242 (13)0.0215 (14)0.0016 (11)0.0102 (12)0.0011 (11)
C5A0.0224 (12)0.0231 (13)0.0228 (14)0.0020 (10)0.0100 (11)0.0010 (11)
C9B0.0312 (14)0.0315 (15)0.0269 (16)0.0014 (12)0.0134 (12)0.0007 (12)
C22A0.0450 (16)0.0326 (15)0.0311 (17)0.0031 (12)0.0119 (13)0.0061 (13)
C2B0.0289 (13)0.0363 (15)0.0219 (15)0.0051 (12)0.0105 (12)0.0011 (12)
C14B0.0383 (15)0.0497 (18)0.0258 (16)0.0107 (13)0.0097 (13)0.0068 (13)
C8B0.0243 (13)0.0228 (13)0.0307 (16)0.0023 (11)0.0119 (12)0.0008 (11)
C22B0.0399 (16)0.0406 (16)0.0386 (18)0.0147 (13)0.0107 (13)0.0014 (14)
C21B0.0270 (14)0.0346 (15)0.0424 (18)0.0033 (11)0.0096 (13)0.0022 (13)
C2A0.0228 (13)0.0233 (14)0.0290 (15)0.0028 (10)0.0067 (11)0.0029 (11)
C5B0.0174 (12)0.0307 (14)0.0200 (14)0.0026 (10)0.0061 (10)0.0025 (11)
C4A0.0253 (13)0.0299 (15)0.0266 (15)0.0017 (11)0.0087 (12)0.0000 (12)
C21A0.0360 (15)0.0322 (15)0.0452 (19)0.0025 (12)0.0159 (14)0.0006 (13)
C14A0.0422 (16)0.0555 (18)0.0331 (17)0.0186 (14)0.0147 (14)0.0190 (14)
C18B0.0538 (18)0.0559 (19)0.0313 (18)0.0101 (15)0.0202 (15)0.0117 (14)
Geometric parameters (Å, º) top
O19A—C6A1.202 (3)C7A—H9A0.9700
O3A—C4A1.357 (3)C7A—H9B0.9700
O3A—C2A1.434 (3)C18A—H10A0.9600
O16A—C11A1.373 (3)C18A—H10B0.9600
O16A—H16A0.8200C18A—H10C0.9600
O1B—C6B1.358 (3)C11B—C12B1.396 (3)
O1B—C2B1.444 (3)C13B—C8B1.384 (3)
O16B—C11B1.382 (3)C13B—C12B1.391 (3)
O16B—H16B0.8200C13B—H120.9300
O17A—C10A1.382 (3)C13A—H130.9300
O17A—C18A1.431 (3)C6A—C5A1.500 (3)
O15B—C12B1.366 (3)C5A—C4A1.513 (3)
O15B—C14B1.434 (3)C5A—H170.9800
O3B—C4B1.360 (3)C9B—C8B1.388 (3)
O3B—C2B1.439 (3)C9B—H180.9300
O15A—C12A1.373 (3)C22A—C2A1.503 (3)
O15A—C14A1.421 (3)C22A—H19A0.9600
O17B—C10B1.379 (3)C22A—H19B0.9600
O17B—C18B1.421 (3)C22A—H19C0.9600
O1A—C6A1.361 (3)C2B—C22B1.506 (3)
O1A—C2A1.441 (3)C2B—C21B1.508 (3)
O20B—C4B1.192 (3)C14B—H21A0.9600
C11A—C12A1.385 (3)C14B—H21B0.9600
C11A—C10A1.388 (3)C14B—H21C0.9600
O19B—C6B1.193 (3)C22B—H23A0.9600
C9A—C8A1.389 (3)C22B—H23B0.9600
C9A—C10A1.391 (3)C22B—H23C0.9600
C9A—H20.9300C21B—H24A0.9600
O20A—C4A1.197 (3)C21B—H24B0.9600
C8A—C13A1.396 (3)C21B—H24C0.9600
C8A—C7A1.509 (3)C2A—C21A1.508 (3)
C10B—C11B1.382 (3)C5B—H260.9800
C10B—C9B1.391 (3)C21A—H28A0.9600
C12A—C13A1.381 (3)C21A—H28B0.9600
C6B—C5B1.507 (3)C21A—H28C0.9600
C7B—C8B1.516 (3)C14A—H29A0.9600
C7B—C5B1.534 (3)C14A—H29B0.9600
C7B—H7A0.9700C14A—H29C0.9600
C7B—H7B0.9700C18B—H30A0.9600
C4B—C5B1.504 (3)C18B—H30B0.9600
C7A—C5A1.539 (3)C18B—H30C0.9600
C4A—O3A—C2A120.85 (17)C4A—C5A—H17106.7
C11A—O16A—H16A109.5C7A—C5A—H17106.7
C6B—O1B—C2B120.49 (19)C8B—C9B—C10B119.4 (2)
C11B—O16B—H16B109.5C8B—C9B—H18120.3
C10A—O17A—C18A117.06 (19)C10B—C9B—H18120.3
C12B—O15B—C14B116.95 (18)C2A—C22A—H19A109.5
C4B—O3B—C2B120.63 (19)C2A—C22A—H19B109.5
C12A—O15A—C14A116.99 (19)H19A—C22A—H19B109.5
C10B—O17B—C18B117.16 (19)C2A—C22A—H19C109.5
C6A—O1A—C2A121.48 (18)H19A—C22A—H19C109.5
O16A—C11A—C12A118.1 (2)H19B—C22A—H19C109.5
O16A—C11A—C10A122.1 (2)O3B—C2B—O1B109.75 (18)
C12A—C11A—C10A119.6 (2)O3B—C2B—C22B105.82 (19)
C8A—C9A—C10A120.1 (2)O1B—C2B—C22B105.7 (2)
C8A—C9A—H2119.9O3B—C2B—C21B111.4 (2)
C10A—C9A—H2119.9O1B—C2B—C21B111.6 (2)
C9A—C8A—C13A119.0 (2)C22B—C2B—C21B112.3 (2)
C9A—C8A—C7A120.0 (2)O15B—C14B—H21A109.5
C13A—C8A—C7A121.0 (2)O15B—C14B—H21B109.5
O17B—C10B—C11B113.8 (2)H21A—C14B—H21B109.5
O17B—C10B—C9B125.2 (2)O15B—C14B—H21C109.5
C11B—C10B—C9B121.0 (2)H21A—C14B—H21C109.5
O15A—C12A—C13A125.2 (2)H21B—C14B—H21C109.5
O15A—C12A—C11A114.8 (2)C13B—C8B—C9B119.7 (2)
C13A—C12A—C11A120.1 (2)C13B—C8B—C7B120.9 (2)
O19B—C6B—O1B118.9 (2)C9B—C8B—C7B119.4 (2)
O19B—C6B—C5B125.5 (2)C2B—C22B—H23A109.5
O1B—C6B—C5B115.6 (2)C2B—C22B—H23B109.5
C8B—C7B—C5B114.44 (19)H23A—C22B—H23B109.5
C8B—C7B—H7A108.7C2B—C22B—H23C109.5
C5B—C7B—H7A108.7H23A—C22B—H23C109.5
C8B—C7B—H7B108.7H23B—C22B—H23C109.5
C5B—C7B—H7B108.7C2B—C21B—H24A109.5
H7A—C7B—H7B107.6C2B—C21B—H24B109.5
O20B—C4B—O3B119.0 (2)H24A—C21B—H24B109.5
O20B—C4B—C5B125.3 (2)C2B—C21B—H24C109.5
O3B—C4B—C5B115.6 (2)H24A—C21B—H24C109.5
C8A—C7A—C5A116.26 (19)H24B—C21B—H24C109.5
C8A—C7A—H9A108.2O3A—C2A—O1A109.85 (16)
C5A—C7A—H9A108.2O3A—C2A—C22A106.17 (19)
C8A—C7A—H9B108.2O1A—C2A—C22A105.08 (19)
C5A—C7A—H9B108.2O3A—C2A—C21A110.85 (19)
H9A—C7A—H9B107.4O1A—C2A—C21A111.27 (19)
O17A—C18A—H10A109.5C22A—C2A—C21A113.3 (2)
O17A—C18A—H10B109.5C4B—C5B—C6B111.15 (19)
H10A—C18A—H10B109.5C4B—C5B—C7B112.9 (2)
O17A—C18A—H10C109.5C6B—C5B—C7B112.5 (2)
H10A—C18A—H10C109.5C4B—C5B—H26106.6
H10B—C18A—H10C109.5C6B—C5B—H26106.6
C10B—C11B—O16B121.6 (2)C7B—C5B—H26106.6
C10B—C11B—C12B119.7 (2)O20A—C4A—O3A118.4 (2)
O16B—C11B—C12B118.7 (2)O20A—C4A—C5A124.8 (2)
C8B—C13B—C12B121.0 (2)O3A—C4A—C5A116.72 (19)
C8B—C13B—H12119.5C2A—C21A—H28A109.5
C12B—C13B—H12119.5C2A—C21A—H28B109.5
C12A—C13A—C8A120.8 (2)H28A—C21A—H28B109.5
C12A—C13A—H13119.6C2A—C21A—H28C109.5
C8A—C13A—H13119.6H28A—C21A—H28C109.5
O19A—C6A—O1A117.4 (2)H28B—C21A—H28C109.5
O19A—C6A—C5A126.5 (2)O15A—C14A—H29A109.5
O1A—C6A—C5A116.1 (2)O15A—C14A—H29B109.5
O17A—C10A—C11A113.6 (2)H29A—C14A—H29B109.5
O17A—C10A—C9A126.1 (2)O15A—C14A—H29C109.5
C11A—C10A—C9A120.3 (2)H29A—C14A—H29C109.5
O15B—C12B—C13B125.3 (2)H29B—C14A—H29C109.5
O15B—C12B—C11B115.5 (2)O17B—C18B—H30A109.5
C13B—C12B—C11B119.2 (2)O17B—C18B—H30B109.5
C6A—C5A—C4A109.77 (19)H30A—C18B—H30B109.5
C6A—C5A—C7A114.36 (19)O17B—C18B—H30C109.5
C4A—C5A—C7A112.26 (18)H30A—C18B—H30C109.5
C6A—C5A—H17106.7H30B—C18B—H30C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O16A—H16A···O17A0.822.262.674 (2)112
O16B—H16B···O17B0.822.222.663 (3)114
C13B—H12···O20B0.932.593.191 (3)123
C13A—H13···O19A0.932.313.056 (3)137
O16A—H16A···O19Bi0.822.292.750 (3)116
O16B—H16B···O17Aii0.822.423.132 (2)145
C5A—H17···O16B0.982.383.329 (3)164
C21B—H24C···O16A0.962.383.310 (3)164
C5B—H26···O16A0.982.473.447 (3)177
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+3/2, y+1/2, z+1/2.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC17H23NO4C16H20O7C15H18O7
Mr305.36324.32310.29
Crystal system, space groupOrthorhombic, PbcaOrthorhombic, PbcaMonoclinic, C2/c
Temperature (K)190190190
a, b, c (Å)15.0721 (4), 11.3109 (3), 19.4443 (4)9.8128 (2), 10.0235 (2), 30.4669 (6)22.9942 (5), 10.1840 (2), 26.9904 (7)
α, β, γ (°)90, 90, 9090, 90, 9090, 112.125 (1), 90
V3)3314.85 (14)2996.68 (10)5855.0 (2)
Z8816
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.090.110.11
Crystal size (mm)0.42 × 0.25 × 0.180.26 × 0.24 × 0.100.32 × 0.14 × 0.10
Data collection
DiffractometerNonius KappaCCD
diffractometer
Nonius KappaCCD
diffractometer
Nonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6647, 3586, 2532 6059, 3374, 2421 11293, 6610, 3333
Rint0.0360.0400.071
(sin θ/λ)max1)0.6390.6480.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.135, 1.05 0.042, 0.105, 1.00 0.056, 0.128, 0.96
No. of reflections358633746610
No. of parameters207213407
No. of restraints001
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.42, 0.320.27, 0.240.26, 0.28

Computer programs: COLLECT (Bruker, 2004), SCALEPACK (Otwinowski & Minor, 1997), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Selected torsion angles (°) in structures (I)–(III) and (VIII) top
(I)(II)(III)(VIII)
H—C5—C7—C8172.7528.94/34.4535.25
C5—C7—C8—C949.1112.6770.70/87.89113.29
Hydrogen-bond geometry (Å, °) for (I)–(III) top
D—H···AD—HH···AD···AD—H···A
Compound (I)
N16—HN16···O20i1.00 (2)1.70 (2)2.688 (2)169 (2)
C10—H2···O3i0.932.463.264 (2)144
C12—H10···O19ii0.932.383.292 (2)168
Compound (II)
C22—H8C···O20iii0.962.583.425 (2)147
C16—H15B···O20iv0.962.553.345 (2)140
Compound (III)
O16A—H16A···O17A0.822.262.674 (2)112
O16B—H16B···O17B0.822.222.663 (3)114
C13B—H12···O20B0.932.593.191 (3)123
C13A—H13···O19A0.932.313.056 (3)137
O16A—H16A···O19Bv0.822.292.750 (3)116
O16B—H16B···O17Avi0.822.423.132 (2)145
Symmetry codes: (i) x-1/2, -y+3/2, -z; (ii) -x-1, y-1/2, -z+1/2, (iii) -x+3/2, y-1/2, z; (iv) x-1, y, z, (v) -x+1, y, -z+1/2; (vi) -x+3/2, y+1/2, -z+1/2.
 

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