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In the crystal structure of the title compound, C19H24O8, the mol­ecules adopt a conformation in which the bulky 2,6-dimethoxy­phen­oxy and 4-hydr­oxy-3,5-dimethoxy­phen­yl groups are almost as far apart as possible. The C(aryl)...C(aryl) distance is 4.8766 (19) Å, which is close to the calculated maximum value (4.92 Å). The C(aryl)-C-C-O(aryloxy) torsion angle is 173.76 (11)° and the C(benzylic)-C-O-C(aryl) torsion angle is 149.09 (11)°. The conformation is compared with those of related lignin model compounds. The hydrogen-bonding pattern is discussed in terms of graph-set theory.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105006359/sk1820sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105006359/sk1820Isup2.hkl
Contains datablock I

CCDC reference: 269052

Comment top

This paper describes the crystal structure of the title threo form, (I), of a lignin model compound representative of structural elements in lignin of the arylglycerol β-syringyl ether type. The crystal structure of the erythro form, (II), has been reported previously (Langer, Li & Lundquist, 2002). Arylglycerol β-syringyl ethers constitute a major type of structural element in hardwood lignins, e.g. in birch lignin (Larsson & Miksche, 1971). The erythro form of such structural elements predominates (Lundquist & von Unge, 1986; Bardet et al., 1998; Akiyama et al., 2003).

In (I), the C9—C10—O6—C12 torsion angle is 149.09 (11)° and the C1—C9—C10—O6 torsion angle is 173.76 (11)° (the enantiomer with the R configuration at the benzylic C atom is considered throughout the discussion of torsion angles in this paper). The C1···C12 distance is 4.8766 (19) Å. In the erythro form, (II), the corresponding data are −75.26 (13)°, −177.27 (10)° and 4.4458 (17) Å, respectively. The C1···C12 distance in (II) is about the same as the corresponding distances in other examined erythro forms of the arylglycerol β-syringyl ether type (Stomberg & Lundquist, 1989; Langer & Lundquist, 2001; Langer et al., 2005). Obviously, the aromatic rings in the erythro form, (II) (and related compounds), are not separated as much as they are in the threo form, (I). The angle between the aromatic ring planes is 67.66 (6)° in (I) and 57.27 (5)° in (II). The C1···C12 distance in (I) [4.8766 (1)9 Å] is very close to the calculated maximum value (4.92 Å).

In the crystal structure of (I), there are three intramolecular (Fig. 1) and two intermolecular hydrogen bonds of the O—H···O type and four intermolecular hydrogen bonds of the weak C—H···O type (Table 1). On the first-level graph-set (Bernstein et al., 1995; Grell et al., 1999), the intramolecular hydrogen bonds are classified as S(5) for bonds a and c, and S(8) for d (Fig. 1). The intermolecular hydrogen bonds b and e form C(10) and C(6) chains, respectively (Fig 2). The weak intramolecular hydrogen bonds f, g, h and i form R22(8) rings and C(8), C(13) and C(7) chains, respectively. On the second-level graph-set, many chains and rings could be identified, the most important ones being C22(10) and C22(16) chain types, both formed by bonds b and e. These two hydrogen bonds thus form R33(22) rings (Fig 2). The assignment of graph-set descriptors was performed using PLUTO, as described by Motherwell et al. (1999). The hydrogen-bonding patterns of threo (I) and erythro (II) (Langer, Li & Lundquist, 2002) are similar with respect to intramolecular hydrogen bonds.

As pointed out above, the title threo β-syringyl ether, (I), adopts a conformation in which the aryl groups are almost as far apart as possible. This is actually what could be expected from computational studies (Besombes et al., 2003a). In a second threo fom of an arylglycerol β-syringyl ether, threo- 2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenoxy)-1,3-propanediol, the C(aryl)—CCO(aryloxy) torsion angle is −70.5 (2)° and the C(aryl)-OCC(benzylic) torsion angle is −148.25 (19)° (Langer, Lundquist et al., 2002). This leads to a C(aryl)···C(aryl) distance of 4.319 (3) Å, which deviates significantly from the maximum value (ca 5 Å). However, according to computational studies, the conformation adopted by this compound is fairly favoured (Besombes et al., 2003a). All the threo forms of models of the arylglycerol β-guaiacyl ether type which have been examined to date [(III) (Stomberg et al., 1988); (IV) and its triacetate (Lundquist et al., 1996); (V) (Langer & Lundquist, 2002)] adopt conformations in which the aromatic groups are far apart from each other. This is in accordance with expectations based on computational studies (Simon & Eriksson, 1998; Besombes et al., 2003b). The crystal structure of the threo form of a trimeric model compound of the arylglyderol β-aryl ether type, (VI), has been reported by Karhunen et al. (1996). Calculations based on their data show that this compound also adopts an extended conformation: the C(aryl)—CCO(aryloxy) torsion angle is 175.7° and the C(aryl)—OCC(benzylic) torsion angle is 171.9°.

Experimental top

threo-2-(2,6-Dimethoxyphenoxy)-1-(4-hydroxy-3,5- dimethoxyphenyl)-1,3-propanediol, (I), was synthesized according to the procedure given by Li et al. (2000). Separation of the erythro and threo forms was accomplished by ion-exchange chromatography (cf. Li et al., 1994). For (I), m.p. 415–417 K. Crystals of (I) suitable for X-ray crystallography were obtained from 2-butanone/ethyl acetate (Ratio?).

Refinement top

H atoms were refined isotropically and were constrained to the ideal geometry using an appropriate riding model. For aromatic H atoms, the C—H distance was kept fixed at 0.95 Å, for secondary H atoms at 0.99 Å and for tertiary at 1.00 Å. For the hydroxyl groups, the O—H distance (0.84 Å) and C—O—H angle (109.5°) were kept fixed, while the torsion angle was allowed to refine, with the starting position based on the circular Fourier synthesis. For methyl groups, the C—H distances (0.98 Å) and C—C—H angles (109.5°) were kept fixed, while the torsion angles were allowed to refine, with the starting position based on the threefold averaged circular Fourier synthesis.

Computing details top

Data collection: SMART(Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2002; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A perspective drawing of (I), showing the atom-numbering scheme. Displacement ellipsoids are shown at the 50% probability level. The intramolecular hydrogen bonds are shown as broken lines and their notation is given in Table 1.
[Figure 2] Fig. 2. The hydrogen-bonding pattern of (I) in projection along the c axis. The hydrogen-bond notation is given in Table 1.
threo-2-(2,6-Dimethoxyphenoxy)-1-(4-hydroxy-3,5-dimethoxyphenyl)propane- 1,3-diol top
Crystal data top
C19H24O8F(000) = 1616
Mr = 380.38Dx = 1.398 Mg m3
Monoclinic, C2/cMelting point = 415–417 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 24.0634 (1) ÅCell parameters from 7395 reflections
b = 7.3465 (1) Åθ = 1.9–30.7°
c = 22.4459 (3) ŵ = 0.11 mm1
β = 114.332 (1)°T = 173 K
V = 3615.56 (7) Å3Prism, colourless
Z = 80.28 × 0.24 × 0.22 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
5566 independent reflections
Radiation source: fine-focus sealed tube4423 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 30.7°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 3434
Tmin = 0.758, Tmax = 0.976k = 1010
28856 measured reflectionsl = 3232
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0693P)2 + 4.0089P]
where P = (Fo2 + 2Fc2)/3
5566 reflections(Δ/σ)max = 0.001
275 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C19H24O8V = 3615.56 (7) Å3
Mr = 380.38Z = 8
Monoclinic, C2/cMo Kα radiation
a = 24.0634 (1) ŵ = 0.11 mm1
b = 7.3465 (1) ÅT = 173 K
c = 22.4459 (3) Å0.28 × 0.24 × 0.22 mm
β = 114.332 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
5566 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
4423 reflections with I > 2σ(I)
Tmin = 0.758, Tmax = 0.976Rint = 0.035
28856 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 1.04Δρmax = 0.55 e Å3
5566 reflectionsΔρmin = 0.27 e Å3
275 parameters
Special details top

Experimental. Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with a LT-2 device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 20 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 7395 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995).

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
O11.26067 (5)0.57058 (19)0.93706 (5)0.0342 (3)
O21.33164 (5)0.60577 (18)0.87428 (5)0.0332 (3)
H21.34950.61960.84940.044 (6)*
O31.28640 (5)0.63279 (19)0.74418 (6)0.0350 (3)
O41.05517 (5)0.77079 (14)0.69355 (6)0.0324 (3)
H41.02260.75060.66060.056 (7)*
O51.07439 (5)0.13622 (14)0.66710 (5)0.0265 (2)
H51.07040.02970.67830.067 (8)*
O60.98651 (4)0.45885 (13)0.66054 (4)0.01855 (19)
O70.97078 (5)0.67472 (15)0.56114 (5)0.0296 (2)
O80.93480 (5)0.13097 (15)0.64410 (6)0.0311 (2)
C11.14385 (6)0.61084 (19)0.76799 (7)0.0230 (3)
C21.16891 (6)0.59072 (19)0.83541 (7)0.0239 (3)
H2A1.14300.57740.85760.027 (5)*
C31.23207 (6)0.5899 (2)0.87086 (7)0.0251 (3)
C41.27024 (6)0.6081 (2)0.83844 (7)0.0249 (3)
C51.24446 (6)0.6239 (2)0.77060 (7)0.0252 (3)
C61.18159 (6)0.6279 (2)0.73525 (7)0.0255 (3)
H61.16460.64230.68910.029 (5)*
C71.22344 (9)0.5300 (3)0.97058 (9)0.0460 (5)
H7A1.19460.62980.96440.057 (7)*
H7B1.24910.51511.01730.060 (7)*
H7C1.20090.41710.95320.058 (7)*
C81.26462 (8)0.6151 (3)0.67552 (8)0.0351 (4)
H8A1.24150.50150.66150.048 (6)*
H8B1.29920.61330.66310.052 (7)*
H8C1.23800.71840.65430.054 (7)*
C91.07530 (6)0.60671 (19)0.73068 (7)0.0220 (3)
H91.05660.60070.76300.023 (4)*
C101.05236 (6)0.44501 (18)0.68448 (6)0.0189 (2)
H101.06430.46150.64710.022 (4)*
C111.07503 (7)0.26098 (19)0.71608 (7)0.0241 (3)
H11A1.11700.27280.75040.044 (6)*
H11B1.04840.21560.73670.031 (5)*
C120.95217 (6)0.39685 (18)0.59825 (6)0.0192 (2)
C130.94180 (6)0.5109 (2)0.54514 (7)0.0235 (3)
C140.90435 (8)0.4543 (2)0.48201 (7)0.0334 (3)
H140.89730.53090.44550.044 (6)*
C150.87777 (8)0.2844 (3)0.47373 (8)0.0367 (4)
H150.85280.24410.43070.048 (6)*
C160.88619 (7)0.1714 (2)0.52561 (8)0.0305 (3)
H160.86670.05600.51840.040 (6)*
C170.92351 (6)0.22747 (19)0.58878 (7)0.0231 (3)
C180.96536 (10)0.7951 (2)0.50902 (9)0.0396 (4)
H18A0.98320.73780.48150.043 (6)*
H18B0.98700.90890.52720.058 (7)*
H18C0.92220.82130.48260.052 (7)*
C190.90465 (9)0.0389 (2)0.63792 (10)0.0365 (4)
H19A0.86040.02050.61610.037 (5)*
H19B0.91510.09090.68140.058 (7)*
H19C0.91760.12240.61200.046 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0231 (5)0.0535 (7)0.0231 (5)0.0006 (5)0.0067 (4)0.0049 (5)
O20.0157 (5)0.0538 (7)0.0264 (5)0.0008 (5)0.0050 (4)0.0034 (5)
O30.0205 (5)0.0563 (8)0.0282 (5)0.0051 (5)0.0100 (4)0.0018 (5)
O40.0255 (5)0.0190 (5)0.0407 (6)0.0022 (4)0.0017 (5)0.0004 (4)
O50.0275 (5)0.0202 (5)0.0326 (5)0.0014 (4)0.0133 (4)0.0006 (4)
O60.0140 (4)0.0221 (5)0.0177 (4)0.0009 (3)0.0046 (3)0.0025 (3)
O70.0373 (6)0.0234 (5)0.0270 (5)0.0005 (4)0.0123 (4)0.0069 (4)
O80.0358 (6)0.0250 (5)0.0321 (6)0.0112 (4)0.0136 (5)0.0004 (4)
C10.0183 (6)0.0209 (6)0.0274 (7)0.0010 (5)0.0070 (5)0.0025 (5)
C20.0205 (6)0.0233 (6)0.0279 (7)0.0011 (5)0.0100 (5)0.0023 (5)
C30.0215 (6)0.0273 (7)0.0234 (6)0.0005 (5)0.0060 (5)0.0002 (5)
C40.0174 (6)0.0266 (7)0.0270 (7)0.0014 (5)0.0055 (5)0.0004 (5)
C50.0193 (6)0.0275 (7)0.0281 (7)0.0035 (5)0.0091 (5)0.0017 (5)
C60.0205 (6)0.0293 (7)0.0242 (6)0.0027 (5)0.0065 (5)0.0011 (5)
C70.0334 (9)0.0759 (15)0.0272 (8)0.0074 (9)0.0109 (7)0.0087 (9)
C80.0296 (8)0.0479 (10)0.0304 (8)0.0054 (7)0.0148 (6)0.0041 (7)
C90.0170 (6)0.0218 (6)0.0250 (6)0.0019 (5)0.0066 (5)0.0032 (5)
C100.0142 (5)0.0214 (6)0.0201 (6)0.0004 (4)0.0062 (4)0.0002 (5)
C110.0238 (6)0.0219 (6)0.0242 (6)0.0045 (5)0.0074 (5)0.0021 (5)
C120.0159 (5)0.0215 (6)0.0187 (6)0.0012 (4)0.0055 (4)0.0020 (5)
C130.0231 (6)0.0248 (6)0.0215 (6)0.0046 (5)0.0082 (5)0.0008 (5)
C140.0338 (8)0.0411 (9)0.0197 (6)0.0096 (7)0.0056 (6)0.0017 (6)
C150.0296 (8)0.0461 (10)0.0240 (7)0.0041 (7)0.0006 (6)0.0116 (7)
C160.0224 (7)0.0304 (7)0.0336 (8)0.0027 (5)0.0063 (6)0.0123 (6)
C170.0190 (6)0.0234 (6)0.0262 (6)0.0007 (5)0.0086 (5)0.0031 (5)
C180.0551 (11)0.0316 (8)0.0412 (9)0.0136 (8)0.0291 (8)0.0161 (7)
C190.0396 (9)0.0227 (7)0.0542 (10)0.0083 (6)0.0261 (8)0.0040 (7)
Geometric parameters (Å, º) top
O1—C31.3635 (18)C7—H7B0.9800
O1—C71.419 (2)C7—H7C0.9800
O2—C41.3605 (17)C8—H8A0.9800
O2—H20.8400C8—H8B0.9800
O3—C51.3666 (18)C8—H8C0.9800
O3—C81.415 (2)C9—C101.5230 (19)
O4—C91.4316 (18)C9—H91.0000
O4—H40.8400C10—C111.5197 (19)
O5—C111.4266 (17)C10—H101.0000
O5—H50.8400C11—H11A0.9900
O6—C121.3758 (15)C11—H11B0.9900
O6—C101.4520 (15)C12—C131.3928 (19)
O7—C131.3631 (19)C12—C171.3958 (19)
O7—C181.4291 (19)C13—C141.393 (2)
O8—C171.3567 (18)C14—C151.380 (3)
O8—C191.4211 (18)C14—H140.9500
C1—C21.387 (2)C15—C161.376 (3)
C1—C61.389 (2)C15—H150.9500
C1—C91.5118 (18)C16—C171.392 (2)
C2—C31.3952 (19)C16—H160.9500
C2—H2A0.9500C18—H18A0.9800
C3—C41.394 (2)C18—H18B0.9800
C4—C51.392 (2)C18—H18C0.9800
C5—C61.3891 (19)C19—H19A0.9800
C6—H60.9500C19—H19B0.9800
C7—H7A0.9800C19—H19C0.9800
C3—O1—C7117.02 (12)C10—C9—H9108.3
C4—O2—H2109.5O6—C10—C11111.23 (11)
C5—O3—C8117.39 (12)O6—C10—C9103.38 (10)
C9—O4—H4109.5C11—C10—C9114.61 (11)
C11—O5—H5109.5O6—C10—H10109.1
C12—O6—C10117.38 (10)C11—C10—H10109.1
C13—O7—C18117.83 (13)C9—C10—H10109.1
C17—O8—C19117.89 (13)O5—C11—C10108.91 (11)
C2—C1—C6120.11 (13)O5—C11—H11A109.9
C2—C1—C9119.14 (12)C10—C11—H11A109.9
C6—C1—C9120.71 (13)O5—C11—H11B109.9
C1—C2—C3120.30 (13)C10—C11—H11B109.9
C1—C2—H2A119.9H11A—C11—H11B108.3
C3—C2—H2A119.9O6—C12—C13119.44 (12)
O1—C3—C2124.34 (13)O6—C12—C17120.15 (12)
O1—C3—C4115.71 (12)C13—C12—C17120.17 (12)
C2—C3—C4119.95 (13)O7—C13—C12114.44 (12)
O2—C4—C5122.26 (13)O7—C13—C14125.30 (14)
O2—C4—C3118.61 (13)C12—C13—C14120.26 (14)
C5—C4—C3119.11 (13)C15—C14—C13118.47 (15)
O3—C5—C6125.19 (13)C15—C14—H14120.8
O3—C5—C4113.73 (12)C13—C14—H14120.8
C6—C5—C4121.07 (13)C14—C15—C16122.25 (14)
C5—C6—C1119.43 (13)C14—C15—H15118.9
C5—C6—H6120.3C16—C15—H15118.9
C1—C6—H6120.3C17—C16—C15119.46 (15)
O1—C7—H7A109.5C17—C16—H16120.3
O1—C7—H7B109.5C15—C16—H16120.3
H7A—C7—H7B109.5O8—C17—C16125.42 (14)
O1—C7—H7C109.5O8—C17—C12115.24 (12)
H7A—C7—H7C109.5C16—C17—C12119.35 (14)
H7B—C7—H7C109.5O7—C18—H18A109.5
O3—C8—H8A109.5O7—C18—H18B109.5
O3—C8—H8B109.5H18A—C18—H18B109.5
H8A—C8—H8B109.5O7—C18—H18C109.5
O3—C8—H8C109.5H18A—C18—H18C109.5
H8A—C8—H8C109.5H18B—C18—H18C109.5
H8B—C8—H8C109.5O8—C19—H19A109.5
O4—C9—C1109.63 (11)O8—C19—H19B109.5
O4—C9—C10108.64 (11)H19A—C19—H19B109.5
C1—C9—C10113.54 (11)O8—C19—H19C109.5
O4—C9—H9108.3H19A—C19—H19C109.5
C1—C9—H9108.3H19B—C19—H19C109.5
C6—C1—C2—C30.8 (2)O4—C9—C10—O663.99 (13)
C9—C1—C2—C3178.55 (13)C1—C9—C10—O6173.76 (11)
C7—O1—C3—C26.8 (2)O4—C9—C10—C11174.79 (11)
C7—O1—C3—C4172.67 (16)C1—C9—C10—C1152.54 (16)
C1—C2—C3—O1179.87 (14)O6—C10—C11—O588.62 (13)
C1—C2—C3—C40.4 (2)C9—C10—C11—O5154.57 (11)
O1—C3—C4—O20.1 (2)C10—O6—C12—C1383.77 (15)
C2—C3—C4—O2179.61 (14)C10—O6—C12—C17101.89 (14)
O1—C3—C4—C5178.41 (14)C18—O7—C13—C12176.37 (13)
C2—C3—C4—C51.1 (2)C18—O7—C13—C143.7 (2)
C8—O3—C5—C610.8 (2)O6—C12—C13—O73.51 (18)
C8—O3—C5—C4168.63 (15)C17—C12—C13—O7177.85 (12)
O2—C4—C5—O31.2 (2)O6—C12—C13—C14176.40 (13)
C3—C4—C5—O3177.24 (14)C17—C12—C13—C142.1 (2)
O2—C4—C5—C6179.30 (14)O7—C13—C14—C15179.48 (15)
C3—C4—C5—C62.2 (2)C12—C13—C14—C150.4 (2)
O3—C5—C6—C1177.57 (15)C13—C14—C15—C161.2 (3)
C4—C5—C6—C11.8 (2)C14—C15—C16—C171.1 (3)
C2—C1—C6—C50.3 (2)C19—O8—C17—C162.3 (2)
C9—C1—C6—C5177.40 (13)C19—O8—C17—C12177.10 (13)
C2—C1—C9—O4123.33 (14)C15—C16—C17—O8178.82 (15)
C6—C1—C9—O458.97 (17)C15—C16—C17—C120.6 (2)
C2—C1—C9—C10114.96 (14)O6—C12—C17—O83.02 (18)
C6—C1—C9—C1062.73 (18)C13—C12—C17—O8177.32 (12)
C12—O6—C10—C1187.44 (13)O6—C12—C17—C16176.42 (12)
C12—O6—C10—C9149.09 (11)C13—C12—C17—C162.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.842.222.6707 (16)114
O2—H2···O5i0.842.022.7851 (15)152
O5—H5···O4ii0.841.992.8284 (15)173
O4—H4···O60.842.312.7424 (14)112
O4—H4···O70.842.132.9123 (16)154
C9—H9···O6iii1.002.563.5139 (17)159
C18—H18C···O2iv0.982.573.466 (2)153
C19—H19C···O7ii0.982.523.491 (2)169
C11—H11A···O3v0.992.503.2171 (18)129
Symmetry codes: (i) x+5/2, y+1/2, z+3/2; (ii) x, y1, z; (iii) x+2, y, z+3/2; (iv) x1/2, y+3/2, z1/2; (v) x+5/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC19H24O8
Mr380.38
Crystal system, space groupMonoclinic, C2/c
Temperature (K)173
a, b, c (Å)24.0634 (1), 7.3465 (1), 22.4459 (3)
β (°) 114.332 (1)
V3)3615.56 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.28 × 0.24 × 0.22
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.758, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
28856, 5566, 4423
Rint0.035
(sin θ/λ)max1)0.718
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.146, 1.04
No. of reflections5566
No. of parameters275
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.55, 0.27

Computer programs: SMART(Siemens, 1995), SAINT (Siemens, 1995), SAINT and SADABS (Sheldrick, 2002, SHELXTL (Bruker, 1997), SHELXTL, DIAMOND (Brandenburg, 2005).

Hydrogen-bonding geometry (Å, °) top
LabelD—H···AD—HH···AD···AD—H···A
aO2—H2···O30.842.222.6707 (16)114
bO2—H2···O5i0.842.022.7851 (15)152
cO4—H4···O60.842.312.7424 (14)112
dO4—H4···O70.842.132.9123 (16)154
eO5—H5···O4ii0.841.992.8284 (15)173
fC9—H9···O6iii1.002.563.5139 (17)159
gC11—H11A···O3iv0.992.503.2171 (18)129
hC18—H18C···O2v0.982.573.466 (2)153
iC19—H19C···O7ii0.982.523.491 (2)169
Symmetry codes: (i) 5/2 − x, 1/2 + y, 3/2 − z; (ii) x, y − 1, z; (iii) 2 − x, y, 3/2 − z; (iv) 5/2 − x, y − 1/2, 3/2 − z; (v) x − 1/2, 3/2 − y, z − 1/2.
 

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