organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(1E,4E)-1,5-Bis(2,4,5-tri­meth­oxy­phen­yl)penta-1,4-dien-3-one1

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
*Correspondence e-mail: hkfun@usm.my

(Received 12 December 2009; accepted 25 December 2009; online 9 January 2010)

There are three mol­ecules in the asymmetric unit of the title compound, C23H26O7, in which the dihedral angles between two benzene rings are 4.34 (9), 18.11 (8) and 8.54 (8)°. The central penta-1,4-dien-3-one fragment makes dihedral angles of 3.95 (9) and 3.32 (16)° with the two adjacent benzene rings in one mol­ecule, whereas the corresponding pairs of angles in the other two mol­ecules are 10.34 (9)/17.46 (8)° and 7.87 (8)/13.33 (8)°. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O and C—H⋯π weak inter­actions into a three-dimensional network. Finally, ππ inter­actions [centroid⋯centroid distances = 3.5984 (10) and 3.5545 (10) Å] are observed.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For a related structure, see: Harrison et al. (2006[Harrison, W. T. A., Sarojini, B. K., Vijaya Raj, K. K., Yathirajan, H. S. & Narayana, B. (2006). Acta Cryst. E62, o1522-o1523.]). For background to and applications of chalcones, see: Baeyer & von Villiger (1902[Baeyer, A. von & Villiger, V. (1902). Chem. Ber. 35, 1201-1212.]); Gomes et al. (2009[Gomes, A., Neuwirth, O., Freitas, M., Couto, D., Ribeiro, D., Figueiredo, A. G. P. R., Silva, A. M. S., Seixas, R. S. G. R., Pinto, D. C. G. A., Tomé, A. C., Cavaleiro, J. A. S., Fernandes, E. & Lima, J. L. F. C. (2009). Bioorg. Med. Chem. 17, 7218-7226.]); Gould et al. (1995[Gould, B. S., Panneerelvam, K., Zacharias, D. E. & Desiraju, G. R. (1995). J. Chem. Soc. Perkin Trans 2, pp. 325-330.]); Masuda et al. (1993[Masuda, T., Jitoe, A., Isobe, J., Nakatani, N. & Yonemori, S. (1993). Phytochemistry, 32, 1557-1560.]); Quincoces et al. (2002[Quincoces, J., Peseke, K., Kordian, M., Carvalho, J., Brunhari, H., Kohn, L. & Antônio, M. (2002). Patent PI 0207141-0, 28.11.2002.]; 2003[Quincoces, J., Peseke, K., Kordian, M., Carvalho, J., Brunhari, H., Kohn, L. & Antônio, M. (2003). Patent PCT/BR 2003/000177.]; 2008[Quincoces, J., Peseke, K., Kordian, M., Carvalho, J., Brunhari, H., Kohn, L. & Antônio, M. (2008). Patent No. US 7,432,401 B2, Oct. 7, 2008.]); Uchida et al. (1998[Uchida, T., Kozawa, K., Sakai, T., Aoki, M., Yoguchi, H., Abduryim, A. & Watanabe, Y. (1998). Mol. Cryst. Liq. Cryst. 315, 135-140.]). For the stability of the temperature controller, see: Cosier & Glazer, (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C23H26O7

  • Mr = 414.44

  • Monoclinic, P 21 /c

  • a = 9.4157 (1) Å

  • b = 36.8613 (5) Å

  • c = 19.1226 (3) Å

  • β = 107.737 (1)°

  • V = 6321.49 (15) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.37 × 0.22 × 0.13 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.988

  • 81495 measured reflections

  • 18387 independent reflections

  • 12498 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.150

  • S = 1.06

  • 18387 reflections

  • 829 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C1C–C6C and C12C–C17C rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C10B—H10B⋯O1Ci 0.93 2.29 3.149 (2) 153
C10C—H10C⋯O1B 0.93 2.33 3.195 (2) 155
C14B—H14B⋯O1Aii 0.93 2.52 3.353 (2) 149
C21A—H21B⋯O3Aiii 0.96 2.49 3.301 (2) 142
C22A—H22C⋯O7Civ 0.96 2.50 3.435 (2) 165
C22B—H22D⋯O2Av 0.96 2.50 3.407 (2) 158
C22B—H22F⋯O1Aii 0.96 2.58 3.227 (2) 125
C23A—H23A⋯O5Ai 0.96 2.52 3.308 (2) 140
C23A—H23C⋯O3C 0.96 2.53 3.452 (2) 161
C23C—H23G⋯O5Ci 0.96 2.54 3.305 (2) 136
C18C—H18HCg4ii 0.96 2.80 3.678 (2) 152
C20A—H20BCg3vi 0.96 2.94 3.855 (2) 159
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -z+1; (iii) -x+2, -y+2, -z+2; (iv) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (v) x, y, z-1; (vi) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Bischalcones with the general formula Ar—CH=CH—CO—CH=CH—Ar (Baeyer & Villiger, 1902) are an important class of compounds because they are widely used in many fields such as in organic solid-state photochemistry (Gould et al., 1995), anti-oxidative and anti-inflammatory activities (Masuda et al., 1993), cytotoxicity (Quincoces et al., 2002; 2003; 2008) and activities involving their non-linear optical (Uchida et al., 1998) and fluorescence properties (Gomes et al., 2009). However not much crystal structures of this type of compound were reported. The title bischalcone (I) was synthesized on the account of its fluorescence property which will be reported elsewhere together with the other bichalcone derivatives. We reported herein the crystal structure of (I).

There are three crystallographic independent molecules A, B and C in the asymmetric unit of (I) (Fig. 1) with slight differences in bond angles. The molecular structure of (I), C23H26O7, is not planar. The dihedral angle between the C1–C6 and C12–C17 benzene rings is 4.34 (9)° in molecule A whereas its is 18.11 (8) and 8.54 (8)° in molecules B and C, respectively. The central penta-1,4-dien-3-one fragment (C7–C11/O1) is planar with the r.m.s. 0.0204 (2) Å for molecule A [0.0227 (2) and 0.0252 (2) Å for molecule B and C, respectively]. This fragment makes the dihedral angles of 3.95 (9) and 3.32 (16)° with the two adjacent C1–C6 and C12–C17 benzene rings, respectively in molecule A whereas the corresponding values are 10.34 (9) and 17.46 (8)° in molecule B; and 7.87 (8) and 13.33 (8)° in the molecule C. The three methoxy groups on C1–C6 benzene ring are essentially planarly attached [C18–O2–C1–C2, C19–O3–C3–C2 and C20–O4–C4–C5 torsion angles of -3.7 (2), 1.4 (3) and -3.9 (2)° in molecule A; -0.2 (3), 3.5 (3) and -1.7 (2)° in molecule B; 3.8 (3), 4.4 (3) and -4.3 (3)° in molecule C]. The middle methoxy group of the 2,4,5-trimethoxyphenyl moeity is co-planar with the C12–C17 benzene ring, with the C22–O6–C15–C14 torsion angle being 1.1 (3)° whereas the other two methoxy groups are twisted with the torsion angles C21–O5–C13–C14 and C23–O7–C16–C17 being -111.48 (18) and -14.4 (3)°, respectively in molecule A [the three corresponding values are -7.6 (3), -30.2 (2) and 9.6 (2)° in molecule B and 0.4 (3), 73.5 (2) and -8.2 (3)° in molecule C]. Intramolecular C—H···O weak interactions (Table 1) generate S(5) ring motifs (Bernstein et al., 1995). The bond distances agree with the literature values (Allen et al., 1987) and are comparable with the related structure (Harrison et al., 2006).

In the crystal packing (Fig. 2), the molecules are linked by intermolecular C—H···O weak interactions (Table 1) into a supramolecular three-dimensional network. The crystal is stabilized by intra- and intermolecular C—H···O weak interactions and C—H···π interactions (Table 1). ππ interactions were observed with the distances of Cg1···Cg4 = 3.5984 (10) Å (symmetry code: x, y, z) and Cg2···Cg5 = 3.5984 (10) Å (symmetry code: 1 + x, 3/2 - y, 1/2 + z); Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of C12A–C17A, C1B–C6B, C12B–C17B, C1C–C6C and C12C–C17B rings, respectively.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For a related structure, see: Harrison et al. (2006). For background to and applications of chalcones, see: Baeyer & von Villiger (1902); Gomes et al. (2009); Gould et al. (1995); Masuda et al. (1993); Quincoces et al. (2002; 2003; 2008); Uchida et al. (1998). For the stability of the temperature controller, see: Cosier & Glazer, (1986).

Experimental top

The title compound was synthesized by dissolving 2,4,5-trimethoxybenzaldehyde (0.5 g, 4.85 mmol) in acetone (50 ml). NaOH 50% aqueous solution (2 ml) was then added. After stirring at room temperature for 1 hr, the resulting orange solid was collected by filtration, washed with distilled water and dried. Pale yellow blocks of (I) were recrystalized from acetone/ethanol (1:1 v/v) by the slow evaporation of the solvent at room temperature after a week, Mp. 441–442 K.

Refinement top

All H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 Å for aromatic and CH; 0.96 Å for CH3 atoms. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is 0.71 Å from C12C and the deepest hole is 0.45 Å from C9A.

Structure description top

Bischalcones with the general formula Ar—CH=CH—CO—CH=CH—Ar (Baeyer & Villiger, 1902) are an important class of compounds because they are widely used in many fields such as in organic solid-state photochemistry (Gould et al., 1995), anti-oxidative and anti-inflammatory activities (Masuda et al., 1993), cytotoxicity (Quincoces et al., 2002; 2003; 2008) and activities involving their non-linear optical (Uchida et al., 1998) and fluorescence properties (Gomes et al., 2009). However not much crystal structures of this type of compound were reported. The title bischalcone (I) was synthesized on the account of its fluorescence property which will be reported elsewhere together with the other bichalcone derivatives. We reported herein the crystal structure of (I).

There are three crystallographic independent molecules A, B and C in the asymmetric unit of (I) (Fig. 1) with slight differences in bond angles. The molecular structure of (I), C23H26O7, is not planar. The dihedral angle between the C1–C6 and C12–C17 benzene rings is 4.34 (9)° in molecule A whereas its is 18.11 (8) and 8.54 (8)° in molecules B and C, respectively. The central penta-1,4-dien-3-one fragment (C7–C11/O1) is planar with the r.m.s. 0.0204 (2) Å for molecule A [0.0227 (2) and 0.0252 (2) Å for molecule B and C, respectively]. This fragment makes the dihedral angles of 3.95 (9) and 3.32 (16)° with the two adjacent C1–C6 and C12–C17 benzene rings, respectively in molecule A whereas the corresponding values are 10.34 (9) and 17.46 (8)° in molecule B; and 7.87 (8) and 13.33 (8)° in the molecule C. The three methoxy groups on C1–C6 benzene ring are essentially planarly attached [C18–O2–C1–C2, C19–O3–C3–C2 and C20–O4–C4–C5 torsion angles of -3.7 (2), 1.4 (3) and -3.9 (2)° in molecule A; -0.2 (3), 3.5 (3) and -1.7 (2)° in molecule B; 3.8 (3), 4.4 (3) and -4.3 (3)° in molecule C]. The middle methoxy group of the 2,4,5-trimethoxyphenyl moeity is co-planar with the C12–C17 benzene ring, with the C22–O6–C15–C14 torsion angle being 1.1 (3)° whereas the other two methoxy groups are twisted with the torsion angles C21–O5–C13–C14 and C23–O7–C16–C17 being -111.48 (18) and -14.4 (3)°, respectively in molecule A [the three corresponding values are -7.6 (3), -30.2 (2) and 9.6 (2)° in molecule B and 0.4 (3), 73.5 (2) and -8.2 (3)° in molecule C]. Intramolecular C—H···O weak interactions (Table 1) generate S(5) ring motifs (Bernstein et al., 1995). The bond distances agree with the literature values (Allen et al., 1987) and are comparable with the related structure (Harrison et al., 2006).

In the crystal packing (Fig. 2), the molecules are linked by intermolecular C—H···O weak interactions (Table 1) into a supramolecular three-dimensional network. The crystal is stabilized by intra- and intermolecular C—H···O weak interactions and C—H···π interactions (Table 1). ππ interactions were observed with the distances of Cg1···Cg4 = 3.5984 (10) Å (symmetry code: x, y, z) and Cg2···Cg5 = 3.5984 (10) Å (symmetry code: 1 + x, 3/2 - y, 1/2 + z); Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of C12A–C17A, C1B–C6B, C12B–C17B, C1C–C6C and C12C–C17B rings, respectively.

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For a related structure, see: Harrison et al. (2006). For background to and applications of chalcones, see: Baeyer & von Villiger (1902); Gomes et al. (2009); Gould et al. (1995); Masuda et al. (1993); Quincoces et al. (2002; 2003; 2008); Uchida et al. (1998). For the stability of the temperature controller, see: Cosier & Glazer, (1986).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids. H atoms of molecules B and C are omitted for clarity.
[Figure 2] Fig. 2. The crystal packing of (I) viewed along the a axis, showing the three-dimensional network. Hydrogen bonds are shown as dashed lines.
(1E,4E)-1,5-Bis(2,4,5-trimethoxyphenyl)penta-1,4-dien-3-one top
Crystal data top
C23H26O7F(000) = 2640
Mr = 414.44Dx = 1.306 Mg m3
Monoclinic, P21/cMelting point = 441–442 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.4157 (1) ÅCell parameters from 18387 reflections
b = 36.8613 (5) Åθ = 1.1–30.0°
c = 19.1226 (3) ŵ = 0.10 mm1
β = 107.737 (1)°T = 100 K
V = 6321.49 (15) Å3Block, colorless
Z = 120.37 × 0.22 × 0.13 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
18387 independent reflections
Radiation source: sealed tube12498 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
phi and ω scansθmax = 30.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1313
Tmin = 0.965, Tmax = 0.988k = 4551
81495 measured reflectionsl = 2626
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0517P)2 + 4.2947P]
where P = (Fo2 + 2Fc2)/3
18387 reflections(Δ/σ)max = 0.002
829 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C23H26O7V = 6321.49 (15) Å3
Mr = 414.44Z = 12
Monoclinic, P21/cMo Kα radiation
a = 9.4157 (1) ŵ = 0.10 mm1
b = 36.8613 (5) ÅT = 100 K
c = 19.1226 (3) Å0.37 × 0.22 × 0.13 mm
β = 107.737 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
18387 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
12498 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.988Rint = 0.046
81495 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.150H-atom parameters constrained
S = 1.06Δρmax = 0.38 e Å3
18387 reflectionsΔρmin = 0.26 e Å3
829 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1A0.61853 (14)0.99343 (4)0.88798 (8)0.0259 (3)
O2A0.77349 (15)1.09843 (4)1.05130 (7)0.0262 (3)
O3A1.27431 (15)1.14769 (4)1.10886 (7)0.0279 (3)
O4A1.34759 (15)1.09825 (4)1.03136 (7)0.0274 (3)
O5A0.47925 (14)0.89473 (3)0.70474 (7)0.0242 (3)
O6A0.83737 (14)0.84534 (3)0.59545 (7)0.0238 (3)
O7A1.03708 (14)0.89136 (4)0.66503 (8)0.0257 (3)
C1A0.9167 (2)1.09853 (5)1.04751 (10)0.0203 (4)
C2A1.0225 (2)1.12410 (5)1.08416 (10)0.0225 (4)
H2AA0.99771.14161.11340.027*
C3A1.1646 (2)1.12340 (5)1.07698 (10)0.0218 (4)
C4A1.2038 (2)1.09658 (5)1.03338 (10)0.0212 (4)
C5A1.0980 (2)1.07165 (5)0.99736 (10)0.0198 (4)
H5AA1.12331.05420.96810.024*
C6A0.95201 (19)1.07169 (5)1.00345 (9)0.0189 (3)
C7A0.84093 (19)1.04502 (5)0.96501 (9)0.0191 (3)
H7AA0.74571.04720.96950.023*
C8A0.86455 (19)1.01757 (5)0.92372 (9)0.0184 (3)
H8AA0.96071.01380.92140.022*
C9A0.74500 (19)0.99314 (5)0.88200 (9)0.0182 (3)
C10A0.78751 (19)0.96863 (5)0.83046 (10)0.0193 (3)
H10A0.88280.97060.82600.023*
C11A0.69497 (19)0.94367 (5)0.78996 (10)0.0190 (3)
H11A0.59980.94240.79490.023*
C12A0.72921 (19)0.91817 (5)0.73880 (9)0.0180 (3)
C13A0.62264 (18)0.89351 (5)0.69924 (10)0.0192 (3)
C14A0.65461 (19)0.86840 (5)0.65119 (10)0.0201 (4)
H14A0.58220.85190.62600.024*
C15A0.79434 (19)0.86815 (5)0.64133 (10)0.0191 (3)
C16A0.90353 (19)0.89331 (5)0.67985 (10)0.0191 (3)
C17A0.87092 (19)0.91748 (5)0.72729 (10)0.0191 (3)
H17A0.94370.93380.75260.023*
C18A0.7343 (2)1.12439 (6)1.09820 (11)0.0297 (4)
H18A0.63221.12091.09640.045*
H18B0.74691.14851.08190.045*
H18C0.79761.12121.14770.045*
C19A1.2386 (2)1.17568 (5)1.15221 (11)0.0315 (5)
H19A1.32101.19221.16830.047*
H19B1.21861.16511.19420.047*
H19C1.15201.18861.12330.047*
C20A1.3885 (2)1.07307 (6)0.98420 (12)0.0319 (5)
H20A1.49081.07690.98670.048*
H20B1.32601.07660.93460.048*
H20C1.37621.04880.99950.048*
C21A0.4405 (2)0.86423 (5)0.74166 (11)0.0258 (4)
H21A0.33440.86360.73230.039*
H21B0.48880.86640.79350.039*
H21C0.47230.84230.72390.039*
C22A0.7279 (2)0.82026 (5)0.55365 (11)0.0271 (4)
H22A0.77090.80550.52400.041*
H22B0.64450.83340.52250.041*
H22C0.69490.80510.58640.041*
C23A1.1351 (2)0.92146 (5)0.68810 (12)0.0271 (4)
H23A1.21720.91920.66850.041*
H23B1.17200.92200.74070.041*
H23C1.08210.94350.67060.041*
O1B0.67886 (14)0.79921 (4)0.36869 (8)0.0296 (3)
O2B0.90239 (14)0.70489 (4)0.53331 (8)0.0273 (3)
O3B1.41632 (14)0.66614 (4)0.58013 (7)0.0267 (3)
O4B1.45884 (14)0.71537 (4)0.49398 (8)0.0297 (3)
O5B0.52194 (14)0.92198 (3)0.26449 (7)0.0223 (3)
O6B0.84488 (14)0.99180 (3)0.15955 (7)0.0236 (3)
O7B1.04120 (13)0.94003 (3)0.19064 (7)0.0213 (3)
C1B1.04099 (19)0.70706 (5)0.52494 (10)0.0201 (4)
C2B1.1587 (2)0.68375 (5)0.56056 (10)0.0202 (4)
H2BA1.14470.66590.59210.024*
C3B1.2953 (2)0.68751 (5)0.54854 (10)0.0209 (4)
C4B1.3190 (2)0.71448 (5)0.50116 (10)0.0220 (4)
C5B1.20241 (19)0.73714 (5)0.46616 (10)0.0204 (4)
H5BA1.21700.75490.43460.024*
C6B1.06154 (19)0.73390 (5)0.47726 (10)0.0191 (3)
C7B0.93671 (19)0.75743 (5)0.44029 (10)0.0195 (3)
H7BA0.84640.75240.44860.023*
C8B0.93721 (19)0.78538 (5)0.39580 (10)0.0201 (4)
H8BA1.02480.79130.38560.024*
C9B0.80148 (18)0.80706 (5)0.36257 (10)0.0183 (3)
C10B0.82631 (19)0.83942 (5)0.32294 (10)0.0199 (4)
H10B0.92000.84240.31690.024*
C11B0.72314 (18)0.86483 (5)0.29492 (9)0.0170 (3)
H11B0.62770.86120.29830.020*
C12B0.75129 (18)0.89799 (4)0.25939 (9)0.0154 (3)
C13B0.64957 (18)0.92681 (5)0.24499 (9)0.0164 (3)
C14B0.67679 (19)0.95861 (5)0.21126 (10)0.0183 (3)
H14B0.60700.97730.20090.022*
C15B0.80799 (19)0.96226 (5)0.19337 (9)0.0170 (3)
C16B0.91373 (18)0.93376 (5)0.20913 (9)0.0169 (3)
C17B0.88319 (18)0.90239 (5)0.24028 (9)0.0171 (3)
H17B0.95170.88350.24900.021*
C18B0.8747 (2)0.67823 (5)0.58179 (11)0.0277 (4)
H18D0.77150.67900.57950.042*
H18E0.93560.68320.63110.042*
H18F0.89850.65460.56740.042*
C19B1.3972 (2)0.63691 (5)0.62517 (11)0.0271 (4)
H19D1.48890.62360.64290.041*
H19E1.32000.62110.59690.041*
H19F1.36980.64630.66600.041*
C20B1.4894 (2)0.74387 (6)0.45006 (13)0.0386 (5)
H20D1.59180.74260.45100.058*
H20E1.47110.76690.46920.058*
H20F1.42580.74130.40040.058*
C21B0.4564 (2)0.95365 (5)0.28354 (11)0.0254 (4)
H21D0.38520.94690.30800.038*
H21E0.40700.96710.23980.038*
H21F0.53260.96850.31570.038*
C22B0.7315 (2)1.01884 (5)0.13343 (12)0.0280 (4)
H22D0.76931.03810.11030.042*
H22E0.70331.02840.17400.042*
H22F0.64611.00810.09850.042*
C23B1.1362 (2)0.90947 (5)0.19467 (11)0.0255 (4)
H23D1.21740.91610.17680.038*
H23E1.08040.89010.16520.038*
H23F1.17470.90160.24470.038*
O1C0.17116 (13)0.85328 (4)0.35904 (7)0.0250 (3)
O2C0.36440 (14)0.94816 (3)0.52907 (7)0.0225 (3)
O3C0.88225 (14)0.98683 (3)0.59876 (7)0.0230 (3)
O4C0.93952 (13)0.93975 (3)0.51207 (7)0.0228 (3)
O5C0.00738 (14)0.74097 (3)0.20661 (7)0.0238 (3)
O6C0.33553 (14)0.68688 (3)0.08487 (7)0.0235 (3)
O7C0.54343 (14)0.73320 (4)0.14497 (8)0.0269 (3)
C1C0.50778 (18)0.94655 (5)0.52632 (9)0.0174 (3)
C2C0.62239 (19)0.96902 (5)0.56811 (9)0.0182 (3)
H2CA0.60310.98600.60000.022*
C3C0.76404 (19)0.96585 (5)0.56170 (9)0.0176 (3)
C4C0.79536 (18)0.94012 (5)0.51384 (10)0.0178 (3)
C5C0.68220 (18)0.91813 (5)0.47306 (9)0.0168 (3)
H5CA0.70240.90120.44130.020*
C6C0.53558 (18)0.92067 (4)0.47832 (9)0.0163 (3)
C7C0.41633 (18)0.89700 (4)0.43687 (9)0.0165 (3)
H7CA0.32060.90290.43740.020*
C8C0.42894 (18)0.86764 (4)0.39794 (9)0.0164 (3)
H8CA0.52300.86060.39670.020*
C9C0.29764 (18)0.84615 (4)0.35702 (9)0.0157 (3)
C10C0.32957 (18)0.81622 (5)0.31329 (9)0.0178 (3)
H10C0.42780.81270.31410.021*
C11C0.22491 (18)0.79370 (5)0.27220 (9)0.0168 (3)
H11C0.12770.79660.27350.020*
C12C0.25297 (18)0.76502 (5)0.22576 (9)0.0167 (3)
C13C0.14380 (18)0.73940 (5)0.19315 (9)0.0180 (3)
C14C0.16725 (19)0.71267 (5)0.14619 (10)0.0197 (3)
H14C0.09280.69580.12540.024*
C15C0.30085 (19)0.71122 (5)0.13060 (10)0.0191 (3)
C16C0.41492 (19)0.73680 (5)0.16373 (10)0.0196 (4)
C17C0.38995 (19)0.76270 (5)0.20996 (10)0.0196 (4)
H17C0.46520.77920.23160.023*
C18C0.3321 (2)0.97249 (5)0.58045 (10)0.0225 (4)
H18G0.22740.97170.57500.034*
H18H0.35970.99670.57140.034*
H18I0.38760.96540.62950.034*
C19C0.8569 (2)1.01450 (5)0.64584 (11)0.0271 (4)
H19G0.94771.02770.66740.041*
H19H0.82441.00360.68390.041*
H19I0.78151.03080.61780.041*
C20C0.9770 (2)0.91258 (6)0.46759 (12)0.0299 (4)
H20G1.08140.91410.47240.045*
H20H0.91970.91630.41720.045*
H20I0.95520.88900.48320.045*
C21C0.0131 (2)0.71272 (6)0.25332 (12)0.0330 (5)
H21G0.11100.71460.25870.049*
H21H0.06040.71490.30060.049*
H21I0.00260.68960.23220.049*
C22C0.2219 (2)0.66088 (5)0.05013 (11)0.0283 (4)
H22G0.25870.64490.02000.042*
H22H0.13520.67340.02020.042*
H22I0.19600.64710.08700.042*
C23C0.6505 (2)0.76178 (5)0.16901 (12)0.0302 (5)
H23G0.73370.75740.15110.045*
H23H0.68430.76250.22170.045*
H23I0.60510.78450.15040.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0184 (6)0.0268 (7)0.0349 (8)0.0002 (5)0.0116 (5)0.0028 (6)
O2A0.0277 (7)0.0229 (7)0.0320 (8)0.0025 (5)0.0152 (6)0.0038 (6)
O3A0.0293 (7)0.0241 (7)0.0269 (7)0.0018 (5)0.0033 (6)0.0076 (6)
O4A0.0213 (7)0.0316 (8)0.0291 (7)0.0044 (5)0.0072 (5)0.0085 (6)
O5A0.0151 (6)0.0236 (7)0.0350 (8)0.0000 (5)0.0092 (5)0.0000 (6)
O6A0.0234 (7)0.0235 (7)0.0270 (7)0.0004 (5)0.0112 (5)0.0027 (5)
O7A0.0188 (6)0.0252 (7)0.0376 (8)0.0012 (5)0.0155 (6)0.0026 (6)
C1A0.0244 (9)0.0181 (9)0.0196 (9)0.0037 (7)0.0084 (7)0.0048 (7)
C2A0.0314 (10)0.0172 (9)0.0183 (9)0.0046 (7)0.0069 (7)0.0014 (7)
C3A0.0266 (9)0.0181 (9)0.0170 (9)0.0005 (7)0.0010 (7)0.0021 (7)
C4A0.0217 (9)0.0228 (9)0.0185 (9)0.0005 (7)0.0054 (7)0.0019 (7)
C5A0.0225 (9)0.0186 (9)0.0175 (9)0.0019 (6)0.0051 (7)0.0018 (7)
C6A0.0217 (9)0.0173 (9)0.0173 (8)0.0018 (6)0.0054 (7)0.0027 (7)
C7A0.0184 (8)0.0195 (9)0.0201 (9)0.0019 (6)0.0071 (7)0.0049 (7)
C8A0.0168 (8)0.0174 (8)0.0212 (9)0.0015 (6)0.0060 (6)0.0036 (7)
C9A0.0193 (8)0.0154 (8)0.0196 (9)0.0027 (6)0.0058 (6)0.0057 (7)
C10A0.0156 (8)0.0211 (9)0.0222 (9)0.0021 (6)0.0072 (6)0.0029 (7)
C11A0.0157 (8)0.0190 (9)0.0231 (9)0.0030 (6)0.0070 (6)0.0044 (7)
C12A0.0165 (8)0.0181 (9)0.0194 (9)0.0017 (6)0.0053 (6)0.0036 (7)
C13A0.0144 (8)0.0190 (9)0.0247 (9)0.0018 (6)0.0065 (6)0.0042 (7)
C14A0.0170 (8)0.0200 (9)0.0222 (9)0.0006 (6)0.0045 (7)0.0016 (7)
C15A0.0211 (9)0.0180 (9)0.0188 (9)0.0029 (6)0.0069 (7)0.0024 (7)
C16A0.0151 (8)0.0199 (9)0.0234 (9)0.0021 (6)0.0076 (6)0.0045 (7)
C17A0.0158 (8)0.0183 (9)0.0227 (9)0.0005 (6)0.0052 (6)0.0021 (7)
C18A0.0340 (11)0.0280 (11)0.0315 (11)0.0058 (8)0.0165 (9)0.0032 (9)
C19A0.0364 (11)0.0216 (10)0.0291 (11)0.0049 (8)0.0010 (8)0.0069 (8)
C20A0.0237 (10)0.0398 (12)0.0347 (11)0.0057 (8)0.0124 (8)0.0117 (9)
C21A0.0184 (9)0.0304 (11)0.0297 (10)0.0001 (7)0.0089 (7)0.0029 (8)
C22A0.0307 (10)0.0241 (10)0.0277 (10)0.0030 (8)0.0107 (8)0.0049 (8)
C23A0.0157 (9)0.0274 (10)0.0399 (12)0.0005 (7)0.0110 (8)0.0049 (9)
O1B0.0167 (6)0.0280 (7)0.0447 (9)0.0014 (5)0.0103 (6)0.0142 (6)
O2B0.0206 (7)0.0277 (7)0.0363 (8)0.0024 (5)0.0125 (6)0.0091 (6)
O3B0.0198 (6)0.0260 (7)0.0323 (8)0.0043 (5)0.0049 (5)0.0127 (6)
O4B0.0185 (7)0.0335 (8)0.0384 (8)0.0035 (5)0.0105 (6)0.0149 (6)
O5B0.0175 (6)0.0169 (6)0.0377 (8)0.0012 (5)0.0159 (5)0.0003 (5)
O6B0.0194 (6)0.0195 (7)0.0342 (8)0.0009 (5)0.0114 (5)0.0082 (6)
O7B0.0169 (6)0.0215 (7)0.0284 (7)0.0008 (5)0.0113 (5)0.0036 (5)
C1B0.0194 (8)0.0194 (9)0.0216 (9)0.0014 (6)0.0064 (7)0.0017 (7)
C2B0.0233 (9)0.0165 (9)0.0192 (9)0.0012 (6)0.0042 (7)0.0016 (7)
C3B0.0201 (9)0.0187 (9)0.0202 (9)0.0022 (6)0.0009 (7)0.0014 (7)
C4B0.0174 (8)0.0238 (9)0.0237 (9)0.0004 (7)0.0047 (7)0.0017 (7)
C5B0.0208 (9)0.0182 (9)0.0213 (9)0.0011 (6)0.0051 (7)0.0028 (7)
C6B0.0188 (8)0.0168 (9)0.0198 (9)0.0007 (6)0.0029 (6)0.0008 (7)
C7B0.0158 (8)0.0197 (9)0.0227 (9)0.0006 (6)0.0051 (6)0.0017 (7)
C8B0.0150 (8)0.0198 (9)0.0251 (9)0.0013 (6)0.0056 (7)0.0012 (7)
C9B0.0154 (8)0.0161 (8)0.0219 (9)0.0005 (6)0.0034 (6)0.0001 (7)
C10B0.0118 (8)0.0207 (9)0.0268 (9)0.0015 (6)0.0055 (6)0.0008 (7)
C11B0.0131 (8)0.0178 (8)0.0204 (9)0.0025 (6)0.0054 (6)0.0011 (7)
C12B0.0143 (8)0.0151 (8)0.0155 (8)0.0016 (6)0.0025 (6)0.0013 (6)
C13B0.0126 (7)0.0169 (8)0.0195 (8)0.0030 (6)0.0047 (6)0.0023 (7)
C14B0.0169 (8)0.0145 (8)0.0224 (9)0.0011 (6)0.0044 (6)0.0014 (7)
C15B0.0179 (8)0.0143 (8)0.0179 (8)0.0024 (6)0.0039 (6)0.0004 (6)
C16B0.0132 (8)0.0205 (9)0.0165 (8)0.0018 (6)0.0040 (6)0.0021 (7)
C17B0.0139 (8)0.0177 (8)0.0189 (8)0.0010 (6)0.0035 (6)0.0009 (7)
C18B0.0292 (10)0.0247 (10)0.0336 (11)0.0028 (8)0.0159 (8)0.0034 (8)
C19B0.0267 (10)0.0226 (10)0.0291 (10)0.0047 (7)0.0042 (8)0.0104 (8)
C20B0.0231 (10)0.0437 (13)0.0514 (14)0.0011 (9)0.0148 (9)0.0236 (11)
C21B0.0282 (10)0.0212 (10)0.0328 (11)0.0048 (7)0.0182 (8)0.0007 (8)
C22B0.0249 (10)0.0202 (10)0.0412 (12)0.0035 (7)0.0138 (8)0.0092 (8)
C23B0.0186 (9)0.0259 (10)0.0354 (11)0.0047 (7)0.0135 (8)0.0057 (8)
O1C0.0131 (6)0.0277 (7)0.0340 (8)0.0007 (5)0.0070 (5)0.0082 (6)
O2C0.0175 (6)0.0241 (7)0.0276 (7)0.0011 (5)0.0093 (5)0.0071 (5)
O3C0.0173 (6)0.0227 (7)0.0262 (7)0.0032 (5)0.0026 (5)0.0091 (5)
O4C0.0134 (6)0.0262 (7)0.0285 (7)0.0025 (5)0.0056 (5)0.0082 (5)
O5C0.0167 (6)0.0236 (7)0.0338 (7)0.0039 (5)0.0118 (5)0.0013 (6)
O6C0.0228 (7)0.0217 (7)0.0272 (7)0.0021 (5)0.0096 (5)0.0085 (5)
O7C0.0189 (6)0.0256 (7)0.0410 (8)0.0032 (5)0.0162 (6)0.0091 (6)
C1C0.0152 (8)0.0168 (8)0.0204 (9)0.0004 (6)0.0058 (6)0.0021 (7)
C2C0.0189 (8)0.0157 (8)0.0187 (8)0.0002 (6)0.0039 (6)0.0011 (7)
C3C0.0181 (8)0.0159 (8)0.0159 (8)0.0013 (6)0.0010 (6)0.0001 (7)
C4C0.0139 (8)0.0181 (9)0.0203 (9)0.0001 (6)0.0039 (6)0.0005 (7)
C5C0.0148 (8)0.0172 (8)0.0176 (8)0.0000 (6)0.0036 (6)0.0006 (7)
C6C0.0156 (8)0.0149 (8)0.0168 (8)0.0009 (6)0.0025 (6)0.0011 (6)
C7C0.0137 (7)0.0168 (8)0.0186 (8)0.0001 (6)0.0043 (6)0.0035 (7)
C8C0.0118 (7)0.0169 (8)0.0199 (8)0.0004 (6)0.0038 (6)0.0002 (7)
C9C0.0149 (8)0.0140 (8)0.0173 (8)0.0008 (6)0.0036 (6)0.0017 (6)
C10C0.0135 (8)0.0174 (8)0.0230 (9)0.0009 (6)0.0062 (6)0.0003 (7)
C11C0.0138 (8)0.0171 (8)0.0202 (9)0.0007 (6)0.0060 (6)0.0017 (7)
C12C0.0161 (8)0.0158 (8)0.0183 (8)0.0006 (6)0.0054 (6)0.0009 (7)
C13C0.0142 (8)0.0191 (9)0.0210 (9)0.0002 (6)0.0058 (6)0.0021 (7)
C14C0.0180 (8)0.0167 (9)0.0227 (9)0.0037 (6)0.0035 (7)0.0018 (7)
C15C0.0203 (8)0.0175 (9)0.0197 (9)0.0002 (6)0.0063 (7)0.0009 (7)
C16C0.0147 (8)0.0199 (9)0.0256 (9)0.0003 (6)0.0081 (7)0.0003 (7)
C17C0.0154 (8)0.0188 (9)0.0243 (9)0.0035 (6)0.0057 (7)0.0028 (7)
C18C0.0220 (9)0.0237 (10)0.0241 (9)0.0004 (7)0.0107 (7)0.0035 (8)
C19C0.0246 (10)0.0252 (10)0.0281 (10)0.0024 (7)0.0028 (8)0.0109 (8)
C20C0.0170 (9)0.0371 (12)0.0367 (11)0.0013 (8)0.0096 (8)0.0126 (9)
C21C0.0330 (11)0.0345 (12)0.0387 (12)0.0051 (9)0.0217 (9)0.0023 (9)
C22C0.0293 (10)0.0265 (10)0.0285 (10)0.0045 (8)0.0079 (8)0.0109 (8)
C23C0.0166 (9)0.0306 (11)0.0469 (13)0.0052 (7)0.0150 (8)0.0111 (9)
Geometric parameters (Å, º) top
O1A—C9A1.230 (2)C11B—C12B1.461 (2)
O2A—C1A1.372 (2)C11B—H11B0.9300
O2A—C18A1.435 (2)C12B—C13B1.401 (2)
O3A—C3A1.363 (2)C12B—C17B1.407 (2)
O3A—C19A1.427 (2)C13B—C14B1.399 (2)
O4A—C4A1.367 (2)C14B—C15B1.385 (2)
O4A—C20A1.426 (2)C14B—H14B0.9300
O5A—C13A1.386 (2)C15B—C16B1.415 (2)
O5A—C21A1.433 (2)C16B—C17B1.371 (2)
O6A—C15A1.363 (2)C17B—H17B0.9300
O6A—C22A1.433 (2)C18B—H18D0.9600
O7A—C16A1.373 (2)C18B—H18E0.9600
O7A—C23A1.425 (2)C18B—H18F0.9600
C1A—C2A1.396 (3)C19B—H19D0.9600
C1A—C6A1.403 (2)C19B—H19E0.9600
C2A—C3A1.386 (3)C19B—H19F0.9600
C2A—H2AA0.9300C20B—H20D0.9600
C3A—C4A1.413 (3)C20B—H20E0.9600
C4A—C5A1.376 (2)C20B—H20F0.9600
C5A—C6A1.415 (2)C21B—H21D0.9600
C5A—H5AA0.9300C21B—H21E0.9600
C6A—C7A1.460 (2)C21B—H21F0.9600
C7A—C8A1.343 (2)C22B—H22D0.9600
C7A—H7AA0.9300C22B—H22E0.9600
C8A—C9A1.472 (2)C22B—H22F0.9600
C8A—H8AA0.9300C23B—H23D0.9600
C9A—C10A1.479 (2)C23B—H23E0.9600
C10A—C11A1.340 (2)C23B—H23F0.9600
C10A—H10A0.9300O1C—C9C1.232 (2)
C11A—C12A1.462 (2)O2C—C1C1.368 (2)
C11A—H11A0.9300O2C—C18C1.430 (2)
C12A—C13A1.394 (2)O3C—C3C1.363 (2)
C12A—C17A1.417 (2)O3C—C19C1.428 (2)
C13A—C14A1.400 (3)O4C—C4C1.368 (2)
C14A—C15A1.385 (2)O4C—C20C1.426 (2)
C14A—H14A0.9300O5C—C13C1.386 (2)
C15A—C16A1.414 (2)O5C—C21C1.423 (2)
C16A—C17A1.371 (2)O6C—C15C1.360 (2)
C17A—H17A0.9300O6C—C22C1.439 (2)
C18A—H18A0.9600O7C—C16C1.369 (2)
C18A—H18B0.9600O7C—C23C1.433 (2)
C18A—H18C0.9600C1C—C2C1.401 (2)
C19A—H19A0.9600C1C—C6C1.403 (2)
C19A—H19B0.9600C2C—C3C1.381 (2)
C19A—H19C0.9600C2C—H2CA0.9300
C20A—H20A0.9600C3C—C4C1.410 (2)
C20A—H20B0.9600C4C—C5C1.376 (2)
C20A—H20C0.9600C5C—C6C1.417 (2)
C21A—H21A0.9600C5C—H5CA0.9300
C21A—H21B0.9600C6C—C7C1.452 (2)
C21A—H21C0.9600C7C—C8C1.339 (2)
C22A—H22A0.9600C7C—H7CA0.9300
C22A—H22B0.9600C8C—C9C1.476 (2)
C22A—H22C0.9600C8C—H8CA0.9300
C23A—H23A0.9600C9C—C10C1.470 (2)
C23A—H23B0.9600C10C—C11C1.344 (2)
C23A—H23C0.9600C10C—H10C0.9300
O1B—C9B1.230 (2)C11C—C12C1.456 (2)
O2B—C1B1.365 (2)C11C—H11C0.9300
O2B—C18B1.428 (2)C12C—C13C1.395 (2)
O3B—C3B1.366 (2)C12C—C17C1.414 (2)
O3B—C19B1.425 (2)C13C—C14C1.395 (2)
O4B—C4B1.366 (2)C14C—C15C1.379 (2)
O4B—C20B1.428 (2)C14C—H14C0.9300
O5B—C13B1.374 (2)C15C—C16C1.425 (2)
O5B—C21B1.419 (2)C16C—C17C1.369 (2)
O6B—C15B1.364 (2)C17C—H17C0.9300
O6B—C22B1.435 (2)C18C—H18G0.9600
O7B—C16B1.370 (2)C18C—H18H0.9600
O7B—C23B1.425 (2)C18C—H18I0.9600
C1B—C6B1.398 (2)C19C—H19G0.9600
C1B—C2B1.404 (2)C19C—H19H0.9600
C2B—C3B1.381 (3)C19C—H19I0.9600
C2B—H2BA0.9300C20C—H20G0.9600
C3B—C4B1.408 (3)C20C—H20H0.9600
C4B—C5B1.379 (2)C20C—H20I0.9600
C5B—C6B1.411 (2)C21C—H21G0.9600
C5B—H5BA0.9300C21C—H21H0.9600
C6B—C7B1.459 (2)C21C—H21I0.9600
C7B—C8B1.337 (3)C22C—H22G0.9600
C7B—H7BA0.9300C22C—H22H0.9600
C8B—C9B1.477 (2)C22C—H22I0.9600
C8B—H8BA0.9300C23C—H23G0.9600
C9B—C10B1.470 (2)C23C—H23H0.9600
C10B—C11B1.338 (2)C23C—H23I0.9600
C10B—H10B0.9300
C1A—O2A—C18A118.38 (15)C13B—C14B—H14B120.1
C3A—O3A—C19A117.03 (16)O6B—C15B—C14B124.72 (15)
C4A—O4A—C20A116.68 (15)O6B—C15B—C16B115.41 (15)
C13A—O5A—C21A114.34 (14)C14B—C15B—C16B119.86 (15)
C15A—O6A—C22A116.90 (14)O7B—C16B—C17B124.78 (15)
C16A—O7A—C23A116.30 (14)O7B—C16B—C15B115.77 (15)
O2A—C1A—C2A122.55 (16)C17B—C16B—C15B119.45 (15)
O2A—C1A—C6A116.50 (16)C16B—C17B—C12B121.93 (16)
C2A—C1A—C6A120.95 (17)C16B—C17B—H17B119.0
C3A—C2A—C1A120.04 (17)C12B—C17B—H17B119.0
C3A—C2A—H2AA120.0O2B—C18B—H18D109.5
C1A—C2A—H2AA120.0O2B—C18B—H18E109.5
O3A—C3A—C2A124.48 (17)H18D—C18B—H18E109.5
O3A—C3A—C4A115.16 (17)O2B—C18B—H18F109.5
C2A—C3A—C4A120.34 (17)H18D—C18B—H18F109.5
O4A—C4A—C5A126.01 (17)H18E—C18B—H18F109.5
O4A—C4A—C3A115.09 (16)O3B—C19B—H19D109.5
C5A—C4A—C3A118.90 (17)O3B—C19B—H19E109.5
C4A—C5A—C6A122.12 (17)H19D—C19B—H19E109.5
C4A—C5A—H5AA118.9O3B—C19B—H19F109.5
C6A—C5A—H5AA118.9H19D—C19B—H19F109.5
C1A—C6A—C5A117.64 (16)H19E—C19B—H19F109.5
C1A—C6A—C7A120.82 (16)O4B—C20B—H20D109.5
C5A—C6A—C7A121.53 (16)O4B—C20B—H20E109.5
C8A—C7A—C6A125.57 (16)H20D—C20B—H20E109.5
C8A—C7A—H7AA117.2O4B—C20B—H20F109.5
C6A—C7A—H7AA117.2H20D—C20B—H20F109.5
C7A—C8A—C9A122.90 (16)H20E—C20B—H20F109.5
C7A—C8A—H8AA118.6O5B—C21B—H21D109.5
C9A—C8A—H8AA118.6O5B—C21B—H21E109.5
O1A—C9A—C8A123.11 (16)H21D—C21B—H21E109.5
O1A—C9A—C10A122.22 (16)O5B—C21B—H21F109.5
C8A—C9A—C10A114.65 (15)H21D—C21B—H21F109.5
C11A—C10A—C9A122.98 (16)H21E—C21B—H21F109.5
C11A—C10A—H10A118.5O6B—C22B—H22D109.5
C9A—C10A—H10A118.5O6B—C22B—H22E109.5
C10A—C11A—C12A126.25 (16)H22D—C22B—H22E109.5
C10A—C11A—H11A116.9O6B—C22B—H22F109.5
C12A—C11A—H11A116.9H22D—C22B—H22F109.5
C13A—C12A—C17A117.40 (16)H22E—C22B—H22F109.5
C13A—C12A—C11A120.89 (16)O7B—C23B—H23D109.5
C17A—C12A—C11A121.71 (16)O7B—C23B—H23E109.5
O5A—C13A—C12A119.63 (16)H23D—C23B—H23E109.5
O5A—C13A—C14A118.70 (16)O7B—C23B—H23F109.5
C12A—C13A—C14A121.61 (16)H23D—C23B—H23F109.5
C15A—C14A—C13A119.79 (16)H23E—C23B—H23F109.5
C15A—C14A—H14A120.1C1C—O2C—C18C118.19 (14)
C13A—C14A—H14A120.1C3C—O3C—C19C117.77 (14)
O6A—C15A—C14A124.94 (16)C4C—O4C—C20C116.72 (14)
O6A—C15A—C16A115.38 (15)C13C—O5C—C21C113.38 (14)
C14A—C15A—C16A119.68 (16)C15C—O6C—C22C116.48 (14)
C17A—C16A—O7A125.07 (16)C16C—O7C—C23C115.83 (14)
C17A—C16A—C15A119.80 (16)O2C—C1C—C2C123.35 (15)
O7A—C16A—C15A115.13 (15)O2C—C1C—C6C115.95 (15)
C16A—C17A—C12A121.71 (16)C2C—C1C—C6C120.70 (15)
C16A—C17A—H17A119.1C3C—C2C—C1C119.73 (16)
C12A—C17A—H17A119.1C3C—C2C—H2CA120.1
O2A—C18A—H18A109.5C1C—C2C—H2CA120.1
O2A—C18A—H18B109.5O3C—C3C—C2C124.29 (16)
H18A—C18A—H18B109.5O3C—C3C—C4C114.83 (15)
O2A—C18A—H18C109.5C2C—C3C—C4C120.88 (15)
H18A—C18A—H18C109.5O4C—C4C—C5C125.64 (16)
H18B—C18A—H18C109.5O4C—C4C—C3C115.35 (15)
O3A—C19A—H19A109.5C5C—C4C—C3C119.01 (16)
O3A—C19A—H19B109.5C4C—C5C—C6C121.57 (16)
H19A—C19A—H19B109.5C4C—C5C—H5CA119.2
O3A—C19A—H19C109.5C6C—C5C—H5CA119.2
H19A—C19A—H19C109.5C1C—C6C—C5C118.11 (15)
H19B—C19A—H19C109.5C1C—C6C—C7C119.90 (15)
O4A—C20A—H20A109.5C5C—C6C—C7C121.98 (15)
O4A—C20A—H20B109.5C8C—C7C—C6C127.18 (16)
H20A—C20A—H20B109.5C8C—C7C—H7CA116.4
O4A—C20A—H20C109.5C6C—C7C—H7CA116.4
H20A—C20A—H20C109.5C7C—C8C—C9C121.77 (15)
H20B—C20A—H20C109.5C7C—C8C—H8CA119.1
O5A—C21A—H21A109.5C9C—C8C—H8CA119.1
O5A—C21A—H21B109.5O1C—C9C—C10C123.05 (15)
H21A—C21A—H21B109.5O1C—C9C—C8C122.05 (15)
O5A—C21A—H21C109.5C10C—C9C—C8C114.90 (14)
H21A—C21A—H21C109.5C11C—C10C—C9C123.76 (15)
H21B—C21A—H21C109.5C11C—C10C—H10C118.1
O6A—C22A—H22A109.5C9C—C10C—H10C118.1
O6A—C22A—H22B109.5C10C—C11C—C12C124.63 (15)
H22A—C22A—H22B109.5C10C—C11C—H11C117.7
O6A—C22A—H22C109.5C12C—C11C—H11C117.7
H22A—C22A—H22C109.5C13C—C12C—C17C117.36 (15)
H22B—C22A—H22C109.5C13C—C12C—C11C121.21 (15)
O7A—C23A—H23A109.5C17C—C12C—C11C121.40 (15)
O7A—C23A—H23B109.5O5C—C13C—C12C119.15 (15)
H23A—C23A—H23B109.5O5C—C13C—C14C119.10 (15)
O7A—C23A—H23C109.5C12C—C13C—C14C121.74 (15)
H23A—C23A—H23C109.5C15C—C14C—C13C120.00 (16)
H23B—C23A—H23C109.5C15C—C14C—H14C120.0
C1B—O2B—C18B119.11 (14)C13C—C14C—H14C120.0
C3B—O3B—C19B117.48 (15)O6C—C15C—C14C125.29 (16)
C4B—O4B—C20B116.76 (15)O6C—C15C—C16C115.24 (15)
C13B—O5B—C21B116.60 (13)C14C—C15C—C16C119.47 (16)
C15B—O6B—C22B116.72 (14)C17C—C16C—O7C125.18 (16)
C16B—O7B—C23B115.94 (14)C17C—C16C—C15C119.61 (16)
O2B—C1B—C6B116.44 (15)O7C—C16C—C15C115.21 (15)
O2B—C1B—C2B123.29 (16)C16C—C17C—C12C121.81 (16)
C6B—C1B—C2B120.27 (16)C16C—C17C—H17C119.1
C3B—C2B—C1B119.69 (16)C12C—C17C—H17C119.1
C3B—C2B—H2BA120.2O2C—C18C—H18G109.5
C1B—C2B—H2BA120.2O2C—C18C—H18H109.5
O3B—C3B—C2B124.24 (16)H18G—C18C—H18H109.5
O3B—C3B—C4B114.66 (16)O2C—C18C—H18I109.5
C2B—C3B—C4B121.10 (16)H18G—C18C—H18I109.5
O4B—C4B—C5B125.85 (17)H18H—C18C—H18I109.5
O4B—C4B—C3B115.39 (16)O3C—C19C—H19G109.5
C5B—C4B—C3B118.76 (17)O3C—C19C—H19H109.5
C4B—C5B—C6B121.41 (17)H19G—C19C—H19H109.5
C4B—C5B—H5BA119.3O3C—C19C—H19I109.5
C6B—C5B—H5BA119.3H19G—C19C—H19I109.5
C1B—C6B—C5B118.77 (16)H19H—C19C—H19I109.5
C1B—C6B—C7B119.06 (16)O4C—C20C—H20G109.5
C5B—C6B—C7B122.17 (16)O4C—C20C—H20H109.5
C8B—C7B—C6B127.45 (16)H20G—C20C—H20H109.5
C8B—C7B—H7BA116.3O4C—C20C—H20I109.5
C6B—C7B—H7BA116.3H20G—C20C—H20I109.5
C7B—C8B—C9B121.37 (16)H20H—C20C—H20I109.5
C7B—C8B—H8BA119.3O5C—C21C—H21G109.5
C9B—C8B—H8BA119.3O5C—C21C—H21H109.5
O1B—C9B—C10B122.79 (15)H21G—C21C—H21H109.5
O1B—C9B—C8B123.08 (16)O5C—C21C—H21I109.5
C10B—C9B—C8B114.11 (15)H21G—C21C—H21I109.5
C11B—C10B—C9B124.36 (16)H21H—C21C—H21I109.5
C11B—C10B—H10B117.8O6C—C22C—H22G109.5
C9B—C10B—H10B117.8O6C—C22C—H22H109.5
C10B—C11B—C12B124.00 (15)H22G—C22C—H22H109.5
C10B—C11B—H11B118.0O6C—C22C—H22I109.5
C12B—C11B—H11B118.0H22G—C22C—H22I109.5
C13B—C12B—C17B117.80 (15)H22H—C22C—H22I109.5
C13B—C12B—C11B121.06 (15)O7C—C23C—H23G109.5
C17B—C12B—C11B121.12 (15)O7C—C23C—H23H109.5
O5B—C13B—C14B122.15 (15)H23G—C23C—H23H109.5
O5B—C13B—C12B116.78 (14)O7C—C23C—H23I109.5
C14B—C13B—C12B121.07 (15)H23G—C23C—H23I109.5
C15B—C14B—C13B119.85 (15)H23H—C23C—H23I109.5
C15B—C14B—H14B120.1
C18A—O2A—C1A—C2A3.7 (2)O1B—C9B—C10B—C11B5.5 (3)
C18A—O2A—C1A—C6A177.34 (16)C8B—C9B—C10B—C11B173.08 (17)
O2A—C1A—C2A—C3A178.51 (16)C9B—C10B—C11B—C12B176.23 (16)
C6A—C1A—C2A—C3A0.4 (3)C10B—C11B—C12B—C13B166.56 (17)
C19A—O3A—C3A—C2A0.2 (3)C10B—C11B—C12B—C17B11.8 (3)
C19A—O3A—C3A—C4A178.80 (16)C21B—O5B—C13B—C14B30.2 (2)
C1A—C2A—C3A—O3A178.18 (16)C21B—O5B—C13B—C12B150.82 (16)
C1A—C2A—C3A—C4A0.8 (3)C17B—C12B—C13B—O5B179.65 (15)
C20A—O4A—C4A—C5A3.8 (3)C11B—C12B—C13B—O5B1.3 (2)
C20A—O4A—C4A—C3A176.10 (17)C17B—C12B—C13B—C14B1.4 (2)
O3A—C3A—C4A—O4A1.9 (2)C11B—C12B—C13B—C14B179.73 (16)
C2A—C3A—C4A—O4A179.01 (16)O5B—C13B—C14B—C15B179.36 (15)
O3A—C3A—C4A—C5A178.01 (16)C12B—C13B—C14B—C15B1.7 (3)
C2A—C3A—C4A—C5A1.1 (3)C22B—O6B—C15B—C14B7.6 (3)
O4A—C4A—C5A—C6A179.13 (17)C22B—O6B—C15B—C16B171.36 (16)
C3A—C4A—C5A—C6A1.0 (3)C13B—C14B—C15B—O6B179.04 (16)
O2A—C1A—C6A—C5A178.71 (15)C13B—C14B—C15B—C16B0.2 (3)
C2A—C1A—C6A—C5A0.3 (3)C23B—O7B—C16B—C17B9.6 (2)
O2A—C1A—C6A—C7A0.8 (2)C23B—O7B—C16B—C15B169.73 (15)
C2A—C1A—C6A—C7A179.84 (16)O6B—C15B—C16B—O7B2.1 (2)
C4A—C5A—C6A—C1A0.6 (3)C14B—C15B—C16B—O7B178.93 (15)
C4A—C5A—C6A—C7A179.88 (16)O6B—C15B—C16B—C17B177.28 (15)
C1A—C6A—C7A—C8A177.55 (17)C14B—C15B—C16B—C17B1.7 (2)
C5A—C6A—C7A—C8A2.9 (3)O7B—C16B—C17B—C12B178.63 (15)
C6A—C7A—C8A—C9A175.45 (16)C15B—C16B—C17B—C12B2.1 (3)
C7A—C8A—C9A—O1A8.2 (3)C13B—C12B—C17B—C16B0.6 (2)
C7A—C8A—C9A—C10A170.30 (16)C11B—C12B—C17B—C16B177.81 (16)
O1A—C9A—C10A—C11A4.0 (3)C18C—O2C—C1C—C2C3.9 (2)
C8A—C9A—C10A—C11A177.49 (16)C18C—O2C—C1C—C6C176.17 (15)
C9A—C10A—C11A—C12A179.03 (16)O2C—C1C—C2C—C3C179.51 (16)
C10A—C11A—C12A—C13A179.58 (17)C6C—C1C—C2C—C3C0.4 (3)
C10A—C11A—C12A—C17A0.4 (3)C19C—O3C—C3C—C2C1.7 (2)
C21A—O5A—C13A—C12A111.48 (18)C19C—O3C—C3C—C4C177.40 (16)
C21A—O5A—C13A—C14A71.4 (2)C1C—C2C—C3C—O3C178.69 (16)
C17A—C12A—C13A—O5A175.63 (15)C1C—C2C—C3C—C4C0.3 (3)
C11A—C12A—C13A—O5A4.3 (2)C20C—O4C—C4C—C5C4.3 (3)
C17A—C12A—C13A—C14A1.4 (3)C20C—O4C—C4C—C3C176.31 (16)
C11A—C12A—C13A—C14A178.64 (16)O3C—C3C—C4C—O4C0.6 (2)
O5A—C13A—C14A—C15A176.04 (16)C2C—C3C—C4C—O4C179.66 (15)
C12A—C13A—C14A—C15A1.0 (3)O3C—C3C—C4C—C5C178.86 (15)
C22A—O6A—C15A—C14A1.1 (3)C2C—C3C—C4C—C5C0.2 (3)
C22A—O6A—C15A—C16A177.98 (15)O4C—C4C—C5C—C6C179.61 (16)
C13A—C14A—C15A—O6A179.14 (16)C3C—C4C—C5C—C6C0.2 (3)
C13A—C14A—C15A—C16A0.1 (3)O2C—C1C—C6C—C5C179.51 (15)
C23A—O7A—C16A—C17A14.4 (3)C2C—C1C—C6C—C5C0.4 (2)
C23A—O7A—C16A—C15A164.98 (16)O2C—C1C—C6C—C7C1.6 (2)
O6A—C15A—C16A—C17A179.90 (15)C2C—C1C—C6C—C7C178.44 (16)
C14A—C15A—C16A—C17A0.8 (3)C4C—C5C—C6C—C1C0.3 (3)
O6A—C15A—C16A—O7A0.5 (2)C4C—C5C—C6C—C7C178.49 (16)
C14A—C15A—C16A—O7A178.62 (16)C1C—C6C—C7C—C8C168.99 (17)
O7A—C16A—C17A—C12A178.97 (16)C5C—C6C—C7C—C8C9.8 (3)
C15A—C16A—C17A—C12A0.3 (3)C6C—C7C—C8C—C9C178.94 (16)
C13A—C12A—C17A—C16A0.7 (3)C7C—C8C—C9C—O1C3.0 (3)
C11A—C12A—C17A—C16A179.33 (16)C7C—C8C—C9C—C10C176.17 (16)
C18B—O2B—C1B—C6B179.45 (16)O1C—C9C—C10C—C11C0.7 (3)
C18B—O2B—C1B—C2B1.4 (3)C8C—C9C—C10C—C11C179.82 (16)
O2B—C1B—C2B—C3B179.33 (17)C9C—C10C—C11C—C12C176.90 (16)
C6B—C1B—C2B—C3B0.2 (3)C10C—C11C—C12C—C13C170.52 (17)
C19B—O3B—C3B—C2B3.5 (3)C10C—C11C—C12C—C17C11.6 (3)
C19B—O3B—C3B—C4B176.27 (16)C21C—O5C—C13C—C12C107.71 (19)
C1B—C2B—C3B—O3B179.63 (17)C21C—O5C—C13C—C14C73.5 (2)
C1B—C2B—C3B—C4B0.2 (3)C17C—C12C—C13C—O5C179.32 (15)
C20B—O4B—C4B—C5B4.4 (3)C11C—C12C—C13C—O5C1.3 (2)
C20B—O4B—C4B—C3B176.09 (18)C17C—C12C—C13C—C14C0.6 (3)
O3B—C3B—C4B—O4B0.2 (2)C11C—C12C—C13C—C14C177.38 (16)
C2B—C3B—C4B—O4B179.97 (17)O5C—C13C—C14C—C15C178.35 (16)
O3B—C3B—C4B—C5B179.36 (16)C12C—C13C—C14C—C15C0.4 (3)
C2B—C3B—C4B—C5B0.5 (3)C22C—O6C—C15C—C14C0.4 (3)
O4B—C4B—C5B—C6B179.85 (17)C22C—O6C—C15C—C16C179.51 (16)
C3B—C4B—C5B—C6B0.3 (3)C13C—C14C—C15C—O6C178.86 (16)
O2B—C1B—C6B—C5B179.52 (16)C13C—C14C—C15C—C16C1.0 (3)
C2B—C1B—C6B—C5B0.4 (3)C23C—O7C—C16C—C17C8.2 (3)
O2B—C1B—C6B—C7B0.1 (2)C23C—O7C—C16C—C15C171.17 (17)
C2B—C1B—C6B—C7B179.22 (16)O6C—C15C—C16C—C17C179.22 (16)
C4B—C5B—C6B—C1B0.1 (3)C14C—C15C—C16C—C17C0.7 (3)
C4B—C5B—C6B—C7B179.51 (17)O6C—C15C—C16C—O7C0.2 (2)
C1B—C6B—C7B—C8B176.72 (18)C14C—C15C—C16C—O7C179.96 (16)
C5B—C6B—C7B—C8B3.7 (3)O7C—C16C—C17C—C12C178.97 (17)
C6B—C7B—C8B—C9B179.50 (17)C15C—C16C—C17C—C12C0.3 (3)
C7B—C8B—C9B—O1B6.0 (3)C13C—C12C—C17C—C16C1.0 (3)
C7B—C8B—C9B—C10B172.61 (17)C11C—C12C—C17C—C16C177.03 (17)
Hydrogen-bond geometry (Å, º) top
Cg3 and Cg4 are the centroids of the C1C–C6C and C12C–C17C rings, respectively.
D—H···AD—HH···AD···AD—H···A
C10B—H10B···O1Ci0.932.293.149 (2)153
C10C—H10C···O1B0.932.333.195 (2)155
C14B—H14B···O1Aii0.932.523.353 (2)149
C21A—H21B···O3Aiii0.962.493.301 (2)142
C22A—H22C···O7Civ0.962.503.435 (2)165
C22B—H22D···O2Av0.962.503.407 (2)158
C22B—H22F···O1Aii0.962.583.227 (2)125
C23A—H23A···O5Ai0.962.523.308 (2)140
C23A—H23C···O3C0.962.533.452 (2)161
C23C—H23G···O5Ci0.962.543.305 (2)136
C18C—H18H···Cg4ii0.962.803.678 (2)152
C20A—H20B···Cg3vi0.962.943.855 (2)159
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+2, z+1; (iii) x+2, y+2, z+2; (iv) x, y+3/2, z+1/2; (v) x, y, z1; (vi) x+2, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC23H26O7
Mr414.44
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)9.4157 (1), 36.8613 (5), 19.1226 (3)
β (°) 107.737 (1)
V3)6321.49 (15)
Z12
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.37 × 0.22 × 0.13
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.965, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
81495, 18387, 12498
Rint0.046
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.150, 1.06
No. of reflections18387
No. of parameters829
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.26

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg3 and Cg4 are the centroids of the C1C–C6C and C12C–C17C rings, respectively.
D—H···AD—HH···AD···AD—H···A
C10B—H10B···O1Ci0.932.293.149 (2)153
C10C—H10C···O1B0.932.333.195 (2)155
C14B—H14B···O1Aii0.932.523.353 (2)149
C21A—H21B···O3Aiii0.962.493.301 (2)142
C22A—H22C···O7Civ0.962.503.435 (2)165
C22B—H22D···O2Av0.962.503.407 (2)158
C22B—H22F···O1Aii0.962.583.227 (2)125
C23A—H23A···O5Ai0.962.523.308 (2)140
C23A—H23C···O3C0.962.533.452 (2)161
C23C—H23G···O5Ci0.962.543.305 (2)136
C18C—H18H···Cg4ii0.962.803.678 (2)152
C20A—H20B···Cg3vi0.962.943.855 (2)159
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+2, z+1; (iii) x+2, y+2, z+2; (iv) x, y+3/2, z+1/2; (v) x, y, z1; (vi) x+2, y+2, z+1.
 

Footnotes

1This paper is dedicated to His Majesty King Bhumibol Adulyadej of Thailand (King Rama IX) for his sustainable development of the country.

Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

PR thanks the Graduate School, Prince of Songkla University, for a research grant. The authors thank Prince of Songkla University for financial support through the Crystal Materials Research Unit. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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