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The title compound, C19H20O6, crystallizes in the centrosymmetric space group P21/c with one mol­ecule in the asymmetric unit. The mol­ecule is approximately planar and the dihedral angle between the phenyl rings is 11.0 (1)°. The H atoms of the central propenone group are trans. There is an intramolecular O—H...O hydrogen bond and the mol­ecules are crosslinked by four intermolecular C—H...O hydrogen bonds, producing a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103008679/na1595sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103008679/na1595Isup2.hkl
Contains datablock I

CCDC reference: 214395

Comment top

Chalcone derivatives possess non-linear optical properties (Fichou et al., 1988). 1,3-Diarylprop-2-enones (chalcones) are of great interest due to their biological activities, viz. antibacterial, antifungal and anti-inflammatory (Ahluwalia et al., 1986; Bhat et al., 1972; Mathew et al., 1984; Oganesyan et al., 1986). They have been widely used as starting materials in many synthetic reactions (Awad et al., 1960; Coudert et al., 1988; Carrie & Rochard, 1963). The main feature of chalcone derivatives is the carbonyl functional group. The carbonyl group plays a significant role in the antibacterial activity of chalcones. Against this background, and in order to obtain detailed information of the solid-state structures, an X-ray study of the title compound, (I), was carried out.

The molecular structure of (I) (Fig. 1) consists of two phenyl rings attached to a propenone group at the 1,3-positions. The molecule is approximately planar, with a dihedral angle between the two phenyl rings of 11.0 (1)°. The two phenyl rings make dihedral angles of 3.5 (1) and 8.6 (1)° with the O4C7—C8C9 group. An analysis of the weighted least-squares plane through the central C6—C7(O4)—C8—C9—C10 chain shows that it is planar, with the largest displacement being 0.011 (2) Å for C8. The H atoms at C8 and C9 are trans.

The bond lengths O1—C13, O2—C14, O3—C15, O5—C1, O6—C3, C8C9 and O4C7 are comparable with the corresponding values in a similar structure (Sharma et al., 1997). The O1 and O6 methoxy groups, which are both in para positions with respect to the point of attachment of the central chain to the benzene rings, show the tendency observed for anisoles to be coplanar with their attached benzene rings; they are oriented in opposite directions with respect to the central chain. The two methoxy groups (O2 and O3) adjacent to O1 are nearly perpendicular and directed on opposite sides of their attached benzene ring. This is obviously due to steric hindrance, the O2···O3 contact distance being 2.780 (2) Å. The orientation of the O3 group is determined by the presence of the adjacent O2 group [O1···O2 = 2.661 (2) Å], while that of the O6 group involves a H16B···H2 contact of 2.29 Å.

The average O—Car [1.373 (3) Å] and O—Csp3 [1.420 (3) Å] bond distances agree well with the corresponding literature values of 1.375 (3) and 1.421 (6) Å, respectively (Domiano et al., 1979). The C—O distances of the two methoxy groups orthogonal to the benzene rings are systematically different: O2—C18 and O3—C19 [average 1.414 (4) Å] tend to be shorter than O1—C17 and O6—C16 [average 1.424 (4) Å], while O2—C14 and O3—C15 [average 1.378 (3) Å] tend to be longer than O1—C13 and O6—C3 [average 1.368 (3) Å]. These differences can be interpreted as due to reduced phenyl–O atom conjugation for the orthogonal O2 and O3 methoxy groups with respect to the nearly coplanar O1 and O6 groups.

Both pairs of exocyclic angles, viz. C1—C6—C7/C5—C6—C7 of 119.1 (2)/124.0 (2)° and C15—C10—C9/C11—C10—C9 of 119.2 (2)/123.2 (2)°, are asymmetric and this is due to the H5A···H8 (2.15 Å) and H11···H8 (2.33 Å) repulsive contacts for those larger than 120°, while those narrower are due to the O5—H5···O4 and C9—H9···O3 attractive contacts. The C1—C6—C5 [116.9 (2)°] and C11—C10—C15 [117.6 (2)°] endocyclic angles at the points of attachment of the benzene rings to the central chain are less than 120° because of hybridization and VSEPR (valence-shell electron-pair repulsion) effects (Domenicano et al., 1975a,b). The deformation of the endocyclic angles is quite similar in the two benzene rings. Interestingly, the endocyclic angles of the two benzene rings are practically equal according to the following values: C1/C15 120.9 (2)/120.9 (2)°, C2/C14 119.7 (2)/119.9 (2)°, C3/C13 120.8 (2)/119.9 (2)°, C4/C12 119.4 (2)/119.6 (2)°, C5/C11 122.1 (2)/122.1 (2)° and C6/C10 116.9 (2)/117.6 (2)°. This finding is indicative of similar behaviour on the ring deformation exerted by the corresponding substitution.

In the solid state, the title molecule is characterized by an intramolecular O5—H5···O4 hydrogen bond in which the hydroxy O atom acts as a donor to the adjacent keto O atom. This hydrogen bond is responsible for the coplanarity of the C1–C6 phenyl with the central propenone chain. This hydrogen bond completes a six-membered ring with atoms O4, C7, C6, C1 and O5 [graph-set descriptor S(6); Bernstein et al., 1995], which adopts a planar conformation.

In addition to normal van der Waals interactions, the crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. Atoms C5 and C17 in the molecule at (x, y, z) act as hydrogen-bond donors to O5 and O3 in the molecule at (x, 1/2 − y, 1/2 + z), respectively. These two hydrogen bonds form an R22(22) ring. The molecules at (x, y, z) and (-x, 1 − y, 1 − z) are linked by C19—H19C···O6 hydrogen bonds into cyclic centrosymmetric R22(26) dimers. Atom C16 in the molecule at (x, y, z) donates one proton to atom O4 in the molecule at (-x, −1/2 + y, 1/2 − z), forming a C(9) chain. Thus, the symmetry-related molecules cross-linked by these hydrogen bonds generate a three-dimensional network (Fig. 2). The geometric details of the hydrogen bonds are given in Table 2.

Experimental top

2-Hydroxy-4-methoxyacetophenone was dissolved in ethanol and crushed KOH was added. The flask was immersed in a bath of crushed ice and a solution of 2,3,4-trimethoxybenzaldehyde in ethanol was added. The reaction mixture was stirred at 300 K and completion of the reaction was monitored by thin-layer chromatography. Ice-cold water was added to the reaction mixture after 48 h and the yellow solid that separated was filtered off, washed with water and cold ethanol, dried and purified by column chromatography on silica gel. Crystals of the title compound were obtained from a mixture of methanol and chlorofom (9:1) by slow evaporation.

Refinement top

All H atoms were fixed geometrically and allowed to ride on their parent atoms, with O—H = 0.82 Å and C—H = 0.93 or 0.96 Å, and Uiso = 1.5 and 1.2Ueq for methyl and other H atoms, respectively.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST(Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (ZORTEP; Zsolnai, 1997), shown with 50% probability displacement ellipsoids. H atoms are displayed as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A plot showing a fragment of the hydrogen-bonded network. The hydrogen bonding is shown as dashed lines (the symmetry codes are as in Table 2). For the sake of clarity, H atoms not participating in hydrogen bonding have been omitted.
1-[2-Hydroxy-4-methoxyphenyl]-3-(2',3',4'-trimethoxyphenyl) prop-2-en-1-one top
Crystal data top
C19H20O6F(000) = 728
Mr = 344.35Dx = 1.331 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.6025 (6) ÅCell parameters from 5955 reflections
b = 8.1908 (2) Åθ = 3.0–28.3°
c = 12.6432 (5) ŵ = 0.10 mm1
β = 92.303 (1)°T = 293 K
V = 1717.93 (10) Å3Rectangular slab, yellow
Z = 40.32 × 0.28 × 0.20 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
4236 independent reflections
Radiation source: fine-focus sealed tube2285 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 3.0°
ω scansh = 2222
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 105
Tmin = 0.969, Tmax = 0.980l = 1615
11685 measured reflections
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.06P)2]
where P = (Fo2 + 2Fc2)/3
4236 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C19H20O6V = 1717.93 (10) Å3
Mr = 344.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.6025 (6) ŵ = 0.10 mm1
b = 8.1908 (2) ÅT = 293 K
c = 12.6432 (5) Å0.32 × 0.28 × 0.20 mm
β = 92.303 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
4236 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
2285 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.980Rint = 0.063
11685 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.148H-atom parameters constrained
S = 1.02Δρmax = 0.20 e Å3
4236 reflectionsΔρmin = 0.31 e Å3
226 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
O10.41006 (8)0.45417 (18)0.90832 (11)0.0593 (4)
O20.44967 (8)0.57618 (18)0.72241 (12)0.0589 (4)
O30.34945 (8)0.53234 (17)0.54318 (10)0.0493 (4)
O40.10647 (9)0.4475 (2)0.37026 (11)0.0665 (5)
O50.01395 (10)0.4101 (2)0.24713 (11)0.0769 (5)
H50.02910.44900.26900.115*
O60.22266 (8)0.0603 (2)0.35541 (12)0.0704 (5)
C10.04430 (11)0.3158 (3)0.32211 (14)0.0482 (5)
C20.11761 (12)0.2396 (3)0.29813 (15)0.0529 (5)
H20.14310.25410.23190.063*
C30.15199 (11)0.1437 (3)0.37208 (16)0.0503 (5)
C40.11468 (11)0.1218 (3)0.47215 (16)0.0549 (5)
H40.13900.05790.52260.066*
C50.04217 (11)0.1952 (3)0.49522 (14)0.0488 (5)
H5A0.01780.18020.56200.059*
C60.00356 (10)0.2920 (2)0.42179 (13)0.0405 (4)
C70.07524 (11)0.3666 (2)0.44133 (14)0.0446 (5)
C80.12035 (11)0.3476 (3)0.54290 (15)0.0476 (5)
H80.09830.28880.59760.057*
C90.19256 (11)0.4146 (2)0.55622 (15)0.0471 (5)
H90.21140.46770.49710.057*
C100.24714 (11)0.4178 (2)0.64935 (14)0.0436 (5)
C110.22606 (12)0.3604 (3)0.74776 (16)0.0540 (5)
H110.17530.31450.75470.065*
C120.27806 (12)0.3694 (3)0.83582 (16)0.0563 (6)
H120.26240.32930.90070.068*
C130.35371 (11)0.4386 (2)0.82676 (16)0.0475 (5)
C140.37646 (10)0.4990 (2)0.72976 (15)0.0433 (5)
C150.32412 (11)0.4864 (2)0.64145 (14)0.0424 (5)
C160.26436 (13)0.0792 (4)0.25545 (19)0.0790 (8)
H16A0.31300.01580.25430.118*
H16B0.23070.04220.20030.118*
H16C0.27750.19220.24430.118*
C170.39444 (15)0.3741 (3)1.00528 (17)0.0697 (7)
H17A0.43800.39451.05570.105*
H17B0.38960.25870.99320.105*
H17C0.34510.41491.03230.105*
C180.51275 (14)0.4777 (4)0.6866 (3)0.0932 (9)
H18A0.56120.54130.68430.140*
H18B0.49860.43740.61700.140*
H18C0.52140.38740.73410.140*
C190.35802 (15)0.7019 (3)0.52485 (19)0.0710 (7)
H19A0.37560.71920.45430.107*
H19B0.39720.74620.57490.107*
H19C0.30710.75510.53300.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0602 (9)0.0626 (10)0.0537 (9)0.0087 (7)0.0162 (7)0.0054 (7)
O20.0438 (8)0.0581 (10)0.0745 (10)0.0144 (7)0.0003 (7)0.0005 (7)
O30.0524 (8)0.0481 (9)0.0480 (8)0.0037 (7)0.0098 (6)0.0002 (6)
O40.0644 (9)0.0903 (13)0.0445 (8)0.0242 (9)0.0006 (7)0.0088 (8)
O50.0924 (12)0.1003 (14)0.0370 (8)0.0345 (10)0.0100 (7)0.0097 (8)
O60.0426 (8)0.0952 (13)0.0725 (10)0.0093 (8)0.0074 (7)0.0135 (9)
C10.0559 (11)0.0544 (13)0.0340 (9)0.0020 (10)0.0014 (8)0.0057 (9)
C20.0551 (12)0.0628 (15)0.0398 (10)0.0027 (11)0.0100 (9)0.0125 (10)
C30.0353 (10)0.0589 (14)0.0564 (12)0.0027 (10)0.0004 (9)0.0155 (11)
C40.0450 (11)0.0683 (15)0.0514 (11)0.0066 (10)0.0014 (9)0.0064 (11)
C50.0437 (10)0.0617 (14)0.0406 (10)0.0000 (10)0.0037 (8)0.0010 (9)
C60.0417 (10)0.0465 (12)0.0334 (9)0.0035 (9)0.0008 (7)0.0052 (8)
C70.0463 (10)0.0503 (12)0.0373 (10)0.0015 (9)0.0042 (8)0.0041 (9)
C80.0451 (10)0.0567 (13)0.0410 (10)0.0027 (10)0.0002 (8)0.0016 (9)
C90.0445 (10)0.0532 (13)0.0439 (10)0.0035 (9)0.0033 (8)0.0023 (9)
C100.0403 (10)0.0446 (12)0.0458 (10)0.0018 (8)0.0001 (8)0.0002 (9)
C110.0440 (11)0.0638 (14)0.0540 (12)0.0144 (10)0.0003 (9)0.0072 (10)
C120.0568 (12)0.0648 (15)0.0470 (11)0.0124 (11)0.0017 (9)0.0093 (10)
C130.0472 (11)0.0425 (12)0.0519 (11)0.0026 (9)0.0068 (9)0.0003 (9)
C140.0398 (10)0.0353 (11)0.0545 (11)0.0032 (8)0.0013 (8)0.0012 (9)
C150.0431 (10)0.0378 (11)0.0468 (11)0.0005 (9)0.0075 (8)0.0005 (8)
C160.0443 (12)0.118 (2)0.0738 (16)0.0003 (13)0.0091 (11)0.0365 (15)
C170.0876 (17)0.0651 (16)0.0548 (13)0.0038 (14)0.0169 (12)0.0088 (12)
C180.0425 (12)0.107 (2)0.130 (3)0.0047 (14)0.0032 (14)0.0010 (19)
C190.0920 (17)0.0545 (15)0.0677 (14)0.0031 (13)0.0180 (13)0.0133 (12)
Geometric parameters (Å, º) top
O1—C131.370 (2)C8—H80.9300
O1—C171.423 (2)C9—C101.457 (3)
O2—C141.376 (2)C9—H90.9300
O2—C181.411 (3)C10—C151.403 (2)
O3—C151.380 (2)C10—C111.388 (3)
O3—C191.416 (3)C11—C121.383 (3)
O4—C71.246 (2)C11—H110.9300
O5—C11.337 (2)C12—C131.387 (3)
O5—H50.8200C12—H120.9300
O6—C31.367 (2)C13—C141.389 (3)
O6—C161.425 (3)C14—C151.391 (3)
C1—C21.390 (3)C16—H16A0.9600
C1—C61.420 (2)C16—H16B0.9600
C2—C31.364 (3)C16—H16C0.9600
C2—H20.9300C17—H17A0.9600
C3—C41.398 (3)C17—H17B0.9600
C4—C51.366 (3)C17—H17C0.9600
C4—H40.9300C18—H18A0.9600
C5—C61.396 (3)C18—H18B0.9600
C5—H5A0.9300C18—H18C0.9600
C6—C71.456 (3)C19—H19A0.9600
C7—C81.469 (3)C19—H19B0.9600
C8—C91.323 (3)C19—H19C0.9600
C13—O1—C17117.6 (2)C10—C11—H11118.9
C14—O2—C18115.4 (2)C13—C12—C11119.56 (18)
C15—O3—C19116.8 (2)C13—C12—H12120.2
C1—O5—H5109.5C11—C12—H12120.2
C3—O6—C16117.8 (2)O1—C13—C12124.69 (18)
O5—C1—C2117.14 (17)O1—C13—C14115.45 (17)
O5—C1—C6121.94 (17)C12—C13—C14119.86 (18)
C2—C1—C6120.93 (18)O2—C14—C15120.32 (17)
C1—C2—C3119.72 (18)O2—C14—C13119.70 (17)
C1—C2—H2120.1C15—C14—C13119.94 (17)
C3—C2—H2120.1O3—C15—C14119.95 (16)
O6—C3—C4115.0 (2)O3—C15—C10119.00 (17)
O6—C3—C2124.2 (2)C14—C15—C10120.93 (17)
C4—C3—C2120.80 (18)O6—C16—H16A109.5
C5—C4—C3119.43 (19)O6—C16—H16B109.5
C5—C4—H4120.3H16A—C16—H16B109.5
C3—C4—H4120.3O6—C16—H16C109.5
C4—C5—C6122.13 (18)H16A—C16—H16C109.5
C4—C5—H5A118.9H16B—C16—H16C109.5
C6—C5—H5A118.9O1—C17—H17A109.5
C5—C6—C1116.9 (2)O1—C17—H17B109.5
C5—C6—C7124.0 (2)H17A—C17—H17B109.5
C1—C6—C7119.1 (2)O1—C17—H17C109.5
O4—C7—C6119.86 (17)H17A—C17—H17C109.5
O4—C7—C8118.34 (17)H17B—C17—H17C109.5
C6—C7—C8121.8 (2)O2—C18—H18A109.5
C9—C8—C7119.66 (18)O2—C18—H18B109.5
C9—C8—H8120.2H18A—C18—H18B109.5
C7—C8—H8120.2O2—C18—H18C109.5
C8—C9—C10129.9 (2)H18A—C18—H18C109.5
C8—C9—H9115.1H18B—C18—H18C109.5
C10—C9—H9115.1O3—C19—H19A109.5
C15—C10—C11117.55 (17)O3—C19—H19B109.5
C15—C10—C9119.22 (16)H19A—C19—H19B109.5
C11—C10—C9123.2 (2)O3—C19—H19C109.5
C12—C11—C10122.13 (18)H19A—C19—H19C109.5
C12—C11—H11118.9H19B—C19—H19C109.5
O5—C1—C2—C3179.13 (19)C15—C10—C11—C120.0 (3)
C6—C1—C2—C31.5 (3)C9—C10—C11—C12177.9 (2)
C16—O6—C3—C4179.1 (2)C10—C11—C12—C130.4 (3)
C16—O6—C3—C22.1 (3)C17—O1—C13—C129.1 (3)
C1—C2—C3—O6178.2 (2)C17—O1—C13—C14171.33 (18)
C1—C2—C3—C40.5 (3)C11—C12—C13—O1179.9 (2)
O6—C3—C4—C5177.57 (18)C11—C12—C13—C140.4 (3)
C2—C3—C4—C51.2 (3)C18—O2—C14—C1585.0 (2)
C3—C4—C5—C60.1 (3)C18—O2—C14—C1397.3 (2)
C4—C5—C6—C12.0 (3)O1—C13—C14—O23.4 (3)
C4—C5—C6—C7177.23 (19)C12—C13—C14—O2176.21 (18)
O5—C1—C6—C5177.99 (19)O1—C13—C14—C15178.81 (17)
C2—C1—C6—C52.7 (3)C12—C13—C14—C151.6 (3)
O5—C1—C6—C72.8 (3)C19—O3—C15—C1472.7 (2)
C2—C1—C6—C7176.54 (18)C19—O3—C15—C10111.3 (2)
C5—C6—C7—O4177.93 (19)O2—C14—C15—O38.3 (3)
C1—C6—C7—O41.3 (3)C13—C14—C15—O3173.94 (17)
C5—C6—C7—C81.2 (3)O2—C14—C15—C10175.73 (17)
C1—C6—C7—C8179.64 (18)C13—C14—C15—C102.0 (3)
O4—C7—C8—C90.6 (3)C11—C10—C15—O3174.77 (18)
C6—C7—C8—C9178.5 (2)C9—C10—C15—O37.2 (3)
C7—C8—C9—C10177.6 (2)C11—C10—C15—C141.2 (3)
C8—C9—C10—C15175.0 (2)C9—C10—C15—C14176.80 (18)
C8—C9—C10—C117.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O40.821.782.503 (2)147
C9—H9···O40.932.332.715 (2)105
C9—H9···O30.932.402.789 (2)105
C19—H19B···O20.962.463.051 (3)120
C5—H5A···O5i0.932.453.315 (2)154
C17—H17B···O3i0.962.563.449 (3)154
C19—H19C···O6ii0.962.533.378 (3)147
C16—H16B···O4iii0.962.413.301 (3)155
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1, z+1; (iii) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H20O6
Mr344.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)16.6025 (6), 8.1908 (2), 12.6432 (5)
β (°) 92.303 (1)
V3)1717.93 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.32 × 0.28 × 0.20
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.969, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
11685, 4236, 2285
Rint0.063
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.148, 1.02
No. of reflections4236
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.31

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003), SHELXL97 and PARST(Nardelli, 1995).

Selected geometric parameters (Å, º) top
O1—C131.370 (2)O4—C71.246 (2)
O1—C171.423 (2)O5—C11.337 (2)
O2—C141.376 (2)O6—C31.367 (2)
O2—C181.411 (3)O6—C161.425 (3)
O3—C151.380 (2)C8—C91.323 (3)
O3—C191.416 (3)
C13—O1—C17117.6 (2)C5—C6—C1116.9 (2)
C14—O2—C18115.4 (2)C5—C6—C7124.0 (2)
C15—O3—C19116.8 (2)C1—C6—C7119.1 (2)
C3—O6—C16117.8 (2)C6—C7—C8121.8 (2)
O6—C3—C4115.0 (2)C8—C9—C10129.9 (2)
O6—C3—C2124.2 (2)C11—C10—C9123.2 (2)
C16—O6—C3—C4179.1 (2)C7—C8—C9—C10177.6 (2)
C16—O6—C3—C22.1 (3)C8—C9—C10—C15175.0 (2)
C1—C6—C7—O41.3 (3)C17—O1—C13—C129.1 (3)
O4—C7—C8—C90.6 (3)C18—O2—C14—C1397.3 (2)
C6—C7—C8—C9178.5 (2)C19—O3—C15—C1472.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O40.821.782.503 (2)147
C9—H9···O40.932.332.715 (2)105
C9—H9···O30.932.402.789 (2)105
C19—H19B···O20.962.463.051 (3)120
C5—H5A···O5i0.932.453.315 (2)154
C17—H17B···O3i0.962.563.449 (3)154
C19—H19C···O6ii0.962.533.378 (3)147
C16—H16B···O4iii0.962.413.301 (3)155
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1, z+1; (iii) x, y1/2, z+1/2.
 

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