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Crystal structure of 3,13-di­meth­oxy-5,6,10,11-tetra­hydrofuro[3,4-i][5]helicene-7,9-dione

aNational Metal and Materials Technology Center (MTEC), 114 Thailand Science, Park, Paholyothin Rd., Klong Luang, Pathumthani, 12120, Thailand
*Correspondence e-mail: somboons@mtec.or.th

Edited by M. Nieger, University of Helsinki, Finland (Received 19 August 2014; accepted 21 October 2014; online 29 October 2014)

The title compound, C26H20O5, crystallizes with two independent molecules (A and B) in the asymmetric unit, which differ primarily in the location of the –OCH3 groups. In the crystal, the mol­ecules form a layered structure parallel to (10-1) by C—H⋯O hydrogen-bonded networks. Adjacent layers are also linked by further C—H⋯O hydrogen bonds, forming a three-dimensional structure.

1. Chemical context

Helicenes are polycyclic aromatic hydro­carbons (PAHs) consisting of ortho-fused aromatic rings arranged in a helical chirality. Among various applications of helicenes (Shen & Chen, 2012[Shen, Y. & Chen, C. F. (2012). Chem. Rev. 112, 1463-1535.]; Gingras, 2013[Gingras, M. (2013). Chem. Soc. Rev. 42, 1051-1095.]), the use of helicene derivatives as light emitters in organic light-emitting diodes has been reported (Sahasithiwat et al., 2010[Sahasithiwat, S., Mophuang, T., Menbangpung, L., Kamtonwong, S. & Sooksimuang, T. (2010). Synth. Met. 160, 1148-1152.]; Shi et al., 2012[Shi, L., Liu, Z., Dong, G., Duan, L., Qiu, Y., Jia, J., Guo, W., Zhao, D., Cui, D. & Tao, X. (2012). Chem. Eur. J. 18, 8092-8099.]). The title compound is a derivative of penta­helicene in which two electron-donating groups, i.e. meth­oxy –OCH3, and an electron-withdrawing group, i.e. di­carb­oxy­lic anhydride –C(=O)OC(=O)–, are added onto the structure. The arrangement of electron donating and withdrawing groups are set into a Λ-shape with the electron-withdrawing group located in the middle, resulting in an effective push–pull system. Moreover, The two rings connected to the central benzene ring are non-aromatic and are in a twist conformation.

[Scheme 1]

2. Structural commentary

The geometric parameters of the title mol­ecule agree well with those reported for similar structures (McIntosh et al., 1954[McIntosh, A. O., Robertson, J. M. & Vand, V. (1954). J. Chem. Soc. pp. 1661-1668.]; Wang et al., 1997[Wang, Z. Y., Qi, Y., Bender, T. P. & Gao, J. P. (1997). Macromolecules, 30, 764-769.]; Stammel et al., 1999[Stammel, C., Fröhlich, R., Wolff, C., Wenck, H., Meijere, A. & Mattay, J. (1999). Eur. J. Org. Chem. 7, 1709-1718.]; Rajapakse et al., 2011[Rajapakse, A., Barnes, C. L. & Gates, K. S. (2011). J. Chem. Crystallogr. 41, 1712-1716.]). The asymmetric unit of the title compound contains two independent mol­ecules (A and B), as shown in Fig. 1[link]. The title compound crystallizes as a racemate in the space group P[\overline{1}]. The enanti­omeric (P)-form is the mirror geometry of the (M)-form. The torsion angle along the inner helical rim of mol­ecule A [C15—C17—C19—C21, −20.3 (3)°] differs from that of mol­ecule B [C15B—C17B—C19B—C21B, 24.8 (3)°] primarily as a result of the differences in the location of their meth­oxy groups. Also, the torsion angles between a terminal ring and a meth­oxy group of mol­ecule A and B of the same form are significantly different, e.g. C24—O2—C12—C13 [−2.9 (4)°] vs C24B—O2B—C12B—C13B [−5.7 (4)] and C23—O1—C3—C2 [170.0 (2)] vs C23B—O1B—C3B—C2B [−176.9 (3)]. Moreover, unlike in another 3,12-dimeth­oxy[5]helicene derivative (Sahasithiwat et al., 2014[Sahasithiwat, S., Sooksimuang, T., Kamtonwong, S., Parnchan, W. & Kangkaew, L. (2014). Acta Cryst. E70, o837.]) where both meth­oxy groups are bent inward, one of meth­oxy groups of the title compound is bent outward. In mol­ecule A, this outward bending results from C23—H23A⋯O3B(x − 1, y − 1, z) hydrogen bonding, while in mol­ecule B, the bending is the result of steric hindrance between atoms C23B and C24B(−x + 1, −y + 1, −z) of paired mol­ecules (Fig. 2[link]).

[Figure 1]
Figure 1
Mol­ecular structure of mol­ecules A and B of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
[Figure 2]
Figure 2
Part of the crystal structure, projected along the a axis, depicting a layer consisting of B mol­ecules linked through hydrogen bonds (blue dashed lines) and connecting to A mol­ecules by further hydrogen bonds. The carbon atoms of mol­ecules A (green) and B (dark gray) are colored differently.

3. Supra­molecular features

In the crystal structure, C—H⋯O hydrogen-bonding inter­actions (Table 1[link]) between B mol­ecules leads to a formation of a mol­ecule B layer (Fig. 2[link]), while C—H⋯O hydrogen-bonding inter­actions involving A mol­ecules leads to the formation of a mol­ecule A layer (Fig. 3[link]). The two layers are positioned alternately parallel to (10[\overline{1}]), as displayed in Fig. 4[link]. Adjacent layers are connected by further C—H⋯O hydrogen bonds, forming a three-dimensional structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1⋯O2i 0.93 2.58 3.304 (3) 135
C23—H23A⋯O3Bii 0.96 2.71 3.666 (3) 177
C6B—H6D⋯O3Biii 0.97 2.68 3.547 (3) 149
C10B—H10C⋯O5Biv 0.97 2.44 3.297 (3) 147
C13B—H13B⋯O5v 0.93 2.56 3.408 (3) 152
C24B—H24D⋯O1Bv 0.96 2.74 3.491 (4) 136
Symmetry codes: (i) -x, -y, -z; (ii) x-1, y-1, z; (iii) -x+2, -y+1, -z+1; (iv) -x+2, -y, -z+1; (v) -x+1, -y+1, -z.
[Figure 3]
Figure 3
Part of the crystal structure, projected along the a axis, depicting a layer consisting of A mol­ecules linked through hydrogen bonds (blue dashed lines) and connecting to B mol­ecules by further hydrogen bonds. The carbon atoms of mol­ecules A (green) and B (dark gray) are colored differently.
[Figure 4]
Figure 4
Packing of the crystal structure, projected along the b axis, showing the layered structure. The carbon atoms of mol­ecule A (green) and B (dark gray) are colored differently.

4. Synthesis and crystallization

The diene 6,6′-dimeth­oxy-3,4,3′,4′-tetra­hydro­[1,1′]bi­naphthalenyl (48 g, 0.15 mol), maleic anhydride (75 g, 0.76 mol) and toluene (65 ml) were place in a 250 ml round-bottom flask and the reaction mixture was stirred at room temperature under an argon atmosphere for 5 days. The resulting mixture was poured into water (300 ml) with vigorous stirring. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 x 100 ml). The combined organic layer was dried with Na2SO4 and the organic solvents were removed to yield a Diels–Alder adduct. The crude product was purified by column chromatography (silica gel, ethyl acetate–hexa­ne) to give the inter­mediate compound (31.67 g, 51%) as a yellow viscous liquid. The Diels–Alder adduct (31 g, 0.07 mol), 2,3-di­chloro-5,6-di­cyano-1,4-benzo­quinone (DDQ) (34 g, 0.15 mol) and xylene (500 ml) were mixed and refluxed for 8 h under an argon atmosphere. The reaction mixture was allowed to cool to room temperature, filtered, and the solid was washed with di­chloro­methane (600 ml). The solvents were removed from the filtrate under reduce pressure to gain the crude product, which was further purified by column chromatography (silica gel, ethyl acetate–hexa­ne) to give the title compound (18.3g, 60%) as a yellow solid, which was characterized by FTIR, 1H-NMR and 13C-NMR. Crystals suitable for X-ray analysis were obtained by slow vapor diffusion of hexane into a solution of the title compound in chloro­form.

4.1. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. All hydrogen atoms were placed in calculated positions and treated as riding atoms with C—H = 0.93–0.97 Å and with Uiso = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula C26H20O5
Mr 412.42
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 296
a, b, c (Å) 8.7570 (9), 15.9008 (16), 16.2987 (16)
α, β, γ (°) 61.695 (3), 84.535 (3), 84.460 (3)
V3) 1985.6 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.42 × 0.34 × 0.16
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2012[Bruker (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.67, 0.75
No. of measured, independent and observed [I > 2σ(I)] reflections 33986, 7072, 4457
Rint 0.049
(sin θ/λ)max−1) 0.597
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.140, 1.02
No. of reflections 7072
No. of parameters 559
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.55, −0.29
Computer programs: APEX2 (Bruker, 2008[Bruker (2008). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2013[Bruker (2013). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS2013 and SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Chemical context top

Helicenes are polycyclic aromatic hydro­carbons (PAHs) consisting of ortho-fused aromatic rings arranged in a helical chirality. Among various applications of helicenes (Shen & Chen, 2012; Gingras, 2013), the use of helicene derivatives as light emitters in organic light-emitting diodes has been reported (Sahasithiwat et al., 2010; Shi et al., 2012). The title compound is a derivative of penta­helicene in which two electron-donating groups, i.e. meth­oxy –OCH3, and an electron-withdrawing group, i.e. di­carb­oxy­lic anhydride –C(=O)OC(=O)–, are added onto the structure. The arrangement of electron donating and withdrawing groups are set into a Λ-shape with the electron-withdrawing group located in the middle, resulting in an effective push–pull system. Moreover, The two rings connected to the central benzene ring are non-aromatic and are in a twist conformation.

Structural commentary top

The geometric parameters of the title molecule agree well with reported similar structures (McIntosh et al., 1954; Wang et al., 1997; Stammel et al., 1999; Rajapakse et al., 2011). The asymmetric unit of the title compound contains two independent molecules (A and B), as shown in Fig. 1. The title compound crystallizes as a racemate in the space group P1. The enanti­omeric (P)-form is the mirror geometry of the (M)-form. The torsion angle along the inner helical rim of molecule A [C15—C17—C19—C21, -20.3 (3)°] differs from that of molecule B [C15B—C17B—C19B—C21B, 24.8 (3)°] primarily as a result of the differences in the location of their meth­oxy groups. Also, the torsion angles between a terminal ring and a meth­oxy group of molecule A and B of the same form are significantly different, e.g. C24—O2—C12—C13 [-2.9 (4)°] vs C24B—O2B—C12B—C13B [-5.7 (4)] and C23—O1—C3—C2 [170.0 (2)] vs C23B—O1B—C3B—C2B [-176.9 (3)]. Moreover, unlike in another 3,12-di­meth­oxy­[5]helicene derivative (Sahasithiwat et al., 2014) where both meth­oxy groups are bent inward, one of meth­oxy groups of the title compound is bent outward. In molecule A, this outward bending results from C23—H23A···O3B(x-1, y-1, z) hydrogen bonding, while in molecule B, the bending is the result of steric hindrance between C23B and C24B(-x+1, -y+1, -z) of paired molecules (Fig.2).

Supra­molecular features top

In the crystal structure, C—H···O hydrogen-bonding inter­actions between B molecules leads to a formation of a molecule B layer (Fig. 2), while C—H···O hydrogen-bonding inter­actions involving A molecules leads to the formation of a molecule A layer (Fig. 3). The two layers are positioned alternately parallel to (101), as displayed in Fig. 4. Adjacent layers are connected by further C—H···O hydrogen bonds, forming a three-dimensional structure.

Synthesis and crystallization top

The diene 6,6'-di­meth­oxy-3,4,3',4'-tetra­hydro­[1,1']binaphthalenyl (48 g, 0.15 mol), maleic anhydride (75 g, 0.76 mol) and toluene (65 ml) were place in a 250 ml round-bottom flask and the reaction mixture was stirred at room temperature under an argon atmosphere for 5 days. The resulting mixture was poured into 300 ml water with vigorous stirring. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3 x 100 ml). The combined organic layer was dried with Na2SO4 and the organic solvents were removed to yield a Diels–Alder adduct. The crude product was purified by column chromatography (silica gel, ethyl acetate–hexane) to give the inter­mediate compound (31.67 g, 51%) as a yellow viscous liquid. The Diels–Alder adduct (31 g, 0.07 mol), 2,3-di­chloro-5,6-di­cyano-1,4-benzo­quinone (DDQ) (34 g, 0.15 mol) and xylene (500 ml) were mixed and refluxed for 8 h under an argon atmosphere. The reaction mixture was allowed to cool to room temperature, filtered, and the solid was washed with di­chloro­methane (600 ml). The solvents were removed from the filtrate under reduce pressure to gain the crude product, which was further purified by column chromatography (silica gel, ethyl acetate–hexane) to give the title compound (18.3g, 60%) as a yellow solid, which was characterized by FTIR, 1H-NMR and 13C-NMR. Crystals suitable for X-ray analysis were obtained by slow vapor diffusion of hexane to a solution of the title compound in chloro­form.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. All hydrogen atoms were placed in calculated positions and treated as riding atoms with C—H distances of 0.93,0.97 and 0.96 Å for aryl, methyl­ene and methyl H atoms, respectively. The H atoms were assigned Uiso = 1.2Ueq(C) for aryl H and methyl­ene H and Uiso = 1.5Ueq(C) for methyl H.

Related literature top

For general information and applications of helicenes, see Shen & Chen (2012); Gingras (2013). For related structure, see: McIntosh et al. (1954); Wang et al. (1997); Stammel et al. (1999); Rajapakse et al. (2011); Sahasithiwat et al. (2014). For an application of helicenes as an emitter in an organic light-emitting diode, see: Sahasithiwat et al. (2010); Shi et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Figures top
Molecular structure of molecules A and B of the title compound showing 50% probability displacement ellipsoids for non-H atoms.

Part of the crystal structure, projected along the a axis, depicting a layer consisting of B molecules linked through hydrogen bonds (blue dashed lines) and connecting to A molecules by further hydrogen bonds. The carbon atoms of molecules A (green) and B (dark gray) are colored differently.

Part of the crystal structure, projected along the a axis, depicting a layer consisting of A molecules linked through hydrogen bonds (blue dashed lines) and connecting to B molecules by further hydrogen bonds. The carbon atoms of molecules A (green) and B (dark gray) are colored differently.

Packing of the crystal structure, projected along the b axis, showing the layered structure. The carbon atoms of molecule A (green) and B (dark gray) are colored differently.
3,13-dimethoxy-5,6,10,11-tetrahydrofuro[3,4-i][5]helicene-7,9-dione top
Crystal data top
C26H20O5Z = 4
Mr = 412.42F(000) = 864
Triclinic, P1Dx = 1.380 Mg m3
a = 8.7570 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.9008 (16) ÅCell parameters from 5829 reflections
c = 16.2987 (16) Åθ = 2.3–21.3°
α = 61.695 (3)°µ = 0.10 mm1
β = 84.535 (3)°T = 296 K
γ = 84.460 (3)°Block, yellow
V = 1985.6 (3) Å30.42 × 0.34 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
4457 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.049
ϕ and ω scansθmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1010
Tmin = 0.67, Tmax = 0.75k = 1818
33986 measured reflectionsl = 1819
7072 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.140 w = 1/[σ2(Fo2) + (0.0675P)2 + 0.2937P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
7072 reflectionsΔρmax = 0.55 e Å3
559 parametersΔρmin = 0.28 e Å3
Crystal data top
C26H20O5γ = 84.460 (3)°
Mr = 412.42V = 1985.6 (3) Å3
Triclinic, P1Z = 4
a = 8.7570 (9) ÅMo Kα radiation
b = 15.9008 (16) ŵ = 0.10 mm1
c = 16.2987 (16) ÅT = 296 K
α = 61.695 (3)°0.42 × 0.34 × 0.16 mm
β = 84.535 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
7072 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
4457 reflections with I > 2σ(I)
Tmin = 0.67, Tmax = 0.75Rint = 0.049
33986 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.02Δρmax = 0.55 e Å3
7072 reflectionsΔρmin = 0.28 e Å3
559 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2293 (2)0.31891 (12)0.40355 (12)0.0598 (5)
O20.1461 (2)0.05931 (15)0.14110 (13)0.0735 (6)
O30.4061 (2)0.25200 (12)0.37700 (13)0.0591 (5)
O40.2984 (2)0.36801 (12)0.24856 (13)0.0593 (5)
O50.1804 (3)0.45029 (13)0.11326 (14)0.0781 (6)
C10.1382 (3)0.06644 (16)0.26419 (16)0.0426 (6)
H10.06550.02810.22170.051*
C20.1326 (3)0.16423 (17)0.30604 (16)0.0467 (6)
H20.05590.19120.29210.056*
C30.2405 (3)0.22305 (16)0.36894 (16)0.0446 (6)
C40.3497 (3)0.18195 (16)0.39277 (15)0.0443 (6)
H40.42070.22080.43620.053*
C50.4635 (3)0.03684 (16)0.38211 (16)0.0425 (6)
H5A0.55070.01600.33720.051*
H5B0.50120.08270.44230.051*
C60.3807 (3)0.04838 (16)0.38856 (15)0.0429 (6)
H6A0.30010.02630.43790.051*
H6B0.45260.08070.40420.051*
C70.2975 (2)0.21484 (16)0.26582 (15)0.0400 (5)
C80.2294 (3)0.27700 (16)0.18311 (16)0.0442 (6)
C90.1102 (3)0.31073 (17)0.03254 (17)0.0557 (7)
H9A0.18940.33560.01740.067*
H9B0.05420.36440.03680.067*
C100.0011 (3)0.25601 (18)0.01103 (18)0.0552 (7)
H10A0.08230.23480.05870.066*
H10B0.04250.29720.04870.066*
C110.0742 (3)0.14675 (18)0.06160 (16)0.0517 (6)
H110.00090.17970.10550.062*
C120.1672 (3)0.07429 (18)0.06706 (16)0.0499 (6)
C130.2755 (3)0.02482 (18)0.00206 (16)0.0489 (6)
H130.33990.02330.00610.059*
C140.2879 (3)0.04721 (16)0.06923 (16)0.0439 (6)
H140.36130.01360.11290.053*
C150.2512 (2)0.02339 (15)0.28425 (15)0.0375 (5)
C160.3536 (2)0.08296 (16)0.35214 (15)0.0381 (5)
C170.2585 (2)0.08169 (15)0.24154 (15)0.0372 (5)
C180.3120 (2)0.11728 (16)0.29812 (15)0.0379 (5)
C190.2096 (2)0.14721 (16)0.15063 (15)0.0383 (5)
C200.1827 (3)0.24554 (16)0.12332 (15)0.0434 (6)
C210.1934 (2)0.11857 (16)0.07733 (15)0.0399 (5)
C220.0884 (3)0.17124 (16)0.00842 (15)0.0441 (6)
C230.3521 (3)0.38130 (18)0.45629 (19)0.0671 (8)
H23A0.32980.44650.47700.101*
H23B0.36310.37200.50940.101*
H23C0.44590.36730.41790.101*
C240.2461 (4)0.0086 (3)0.1551 (2)0.0984 (12)
H24A0.21900.01130.20950.148*
H24B0.23710.07040.10160.148*
H24C0.35000.00980.16380.148*
C250.3434 (3)0.27254 (18)0.30762 (19)0.0476 (6)
C260.2271 (3)0.37458 (19)0.1722 (2)0.0552 (7)
O1B0.4341 (3)0.70645 (14)0.20432 (14)0.0874 (7)
O2B0.5797 (2)0.27135 (14)0.06882 (13)0.0675 (5)
O3B1.2533 (2)0.37305 (14)0.53046 (14)0.0757 (6)
O4B1.22652 (19)0.22009 (12)0.56595 (11)0.0583 (5)
O5B1.1588 (2)0.08717 (13)0.56674 (13)0.0664 (5)
C1B0.6213 (3)0.47154 (17)0.28976 (16)0.0464 (6)
H1B0.59270.40990.30860.056*
C2B0.5121 (3)0.54570 (18)0.26048 (17)0.0527 (7)
H2B0.41020.53450.25930.063*
C3B0.5538 (3)0.63758 (18)0.23254 (17)0.0559 (7)
C4B0.7039 (3)0.65447 (17)0.23540 (17)0.0556 (7)
H4B0.73090.71640.21660.067*
C5B0.9769 (3)0.59131 (17)0.27941 (19)0.0616 (7)
H5C0.98480.65390.27470.074*
H5D1.04510.58660.23110.074*
C6B1.0240 (3)0.51389 (16)0.37485 (18)0.0547 (7)
H6C1.13100.51870.38180.066*
H6D0.96270.52300.42310.066*
C7B1.0800 (3)0.33363 (16)0.44698 (15)0.0412 (6)
C8B1.0537 (2)0.24431 (16)0.45687 (15)0.0410 (6)
C9B0.9301 (3)0.13854 (16)0.40664 (17)0.0481 (6)
H9C0.94100.08870.47040.058*
H9D1.00550.12410.36680.058*
C10B0.7705 (3)0.14050 (15)0.37765 (16)0.0470 (6)
H10C0.75590.08060.37810.056*
H10D0.69480.14770.42170.056*
C11B0.6746 (3)0.21266 (17)0.21564 (17)0.0452 (6)
H11B0.63740.15410.23010.054*
C12B0.6552 (3)0.28971 (18)0.12756 (17)0.0466 (6)
C13B0.7156 (3)0.37574 (17)0.10419 (16)0.0485 (6)
H13B0.70630.42700.04470.058*
C14B0.7905 (3)0.38470 (16)0.17052 (16)0.0450 (6)
H14B0.83270.44240.15430.054*
C15B0.7752 (3)0.48667 (15)0.29184 (15)0.0413 (6)
C16B0.8150 (3)0.57949 (16)0.26625 (16)0.0484 (6)
C17B0.8906 (3)0.40605 (15)0.33414 (15)0.0394 (5)
C18B1.0014 (3)0.41609 (16)0.38601 (16)0.0415 (6)
C19B0.8840 (2)0.31768 (15)0.33252 (15)0.0371 (5)
C20B0.9591 (2)0.23375 (15)0.39936 (15)0.0391 (5)
C21B0.8044 (2)0.31013 (15)0.26054 (15)0.0370 (5)
C22B0.7482 (2)0.22162 (15)0.28218 (15)0.0383 (5)
C23B0.4664 (5)0.7987 (2)0.1717 (3)0.1213 (15)
H23D0.37330.83870.15480.182*
H23E0.53660.81750.11780.182*
H23F0.51230.80550.21920.182*
C24B0.5497 (4)0.3489 (2)0.0203 (2)0.0901 (10)
H24D0.49580.32720.05470.135*
H24E0.64500.37370.05370.135*
H24F0.48790.39840.01290.135*
C25B1.1926 (3)0.3186 (2)0.51467 (18)0.0534 (7)
C26B1.1451 (3)0.17239 (19)0.53251 (17)0.0498 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0713 (12)0.0406 (10)0.0656 (12)0.0097 (9)0.0121 (10)0.0208 (9)
O20.0628 (12)0.1206 (17)0.0705 (12)0.0183 (11)0.0239 (10)0.0726 (13)
O30.0602 (11)0.0715 (13)0.0662 (12)0.0122 (9)0.0033 (10)0.0477 (10)
O40.0737 (12)0.0499 (11)0.0646 (12)0.0148 (9)0.0019 (10)0.0343 (10)
O50.1114 (17)0.0406 (12)0.0715 (14)0.0087 (11)0.0069 (12)0.0163 (11)
C10.0413 (13)0.0467 (15)0.0422 (14)0.0038 (11)0.0092 (11)0.0215 (12)
C20.0435 (14)0.0499 (16)0.0515 (15)0.0100 (11)0.0077 (12)0.0256 (13)
C30.0514 (15)0.0410 (14)0.0443 (14)0.0099 (11)0.0008 (12)0.0214 (12)
C40.0509 (15)0.0418 (14)0.0398 (13)0.0001 (11)0.0115 (11)0.0177 (12)
C50.0413 (13)0.0473 (14)0.0422 (13)0.0033 (11)0.0116 (11)0.0219 (12)
C60.0473 (14)0.0490 (15)0.0392 (13)0.0090 (11)0.0072 (11)0.0244 (12)
C70.0402 (13)0.0441 (14)0.0391 (13)0.0093 (10)0.0029 (10)0.0220 (12)
C80.0488 (14)0.0385 (14)0.0451 (15)0.0076 (11)0.0059 (11)0.0200 (12)
C90.0667 (18)0.0458 (15)0.0484 (15)0.0065 (13)0.0072 (13)0.0181 (13)
C100.0546 (16)0.0589 (17)0.0472 (15)0.0137 (13)0.0142 (12)0.0220 (13)
C110.0430 (14)0.0713 (18)0.0426 (14)0.0054 (13)0.0138 (11)0.0277 (14)
C120.0417 (14)0.0731 (18)0.0449 (14)0.0003 (13)0.0078 (12)0.0356 (14)
C130.0468 (15)0.0594 (16)0.0494 (15)0.0053 (12)0.0068 (12)0.0336 (13)
C140.0400 (13)0.0516 (15)0.0429 (14)0.0037 (11)0.0106 (11)0.0242 (12)
C150.0391 (13)0.0423 (14)0.0349 (12)0.0025 (10)0.0059 (10)0.0205 (11)
C160.0389 (13)0.0447 (14)0.0353 (13)0.0045 (10)0.0037 (10)0.0217 (11)
C170.0331 (12)0.0415 (14)0.0401 (13)0.0020 (10)0.0021 (10)0.0217 (11)
C180.0365 (12)0.0433 (14)0.0376 (13)0.0053 (10)0.0008 (10)0.0216 (11)
C190.0349 (12)0.0445 (14)0.0365 (13)0.0002 (10)0.0048 (10)0.0197 (11)
C200.0477 (14)0.0407 (14)0.0390 (13)0.0011 (11)0.0019 (11)0.0169 (11)
C210.0405 (13)0.0451 (14)0.0346 (13)0.0010 (11)0.0052 (10)0.0189 (11)
C220.0407 (13)0.0520 (15)0.0377 (13)0.0028 (11)0.0064 (11)0.0197 (12)
C230.088 (2)0.0438 (16)0.0642 (18)0.0012 (15)0.0185 (16)0.0187 (14)
C240.068 (2)0.172 (4)0.115 (3)0.028 (2)0.0244 (19)0.119 (3)
C250.0458 (15)0.0491 (16)0.0543 (16)0.0113 (12)0.0076 (13)0.0299 (14)
C260.0631 (17)0.0448 (17)0.0548 (17)0.0122 (13)0.0091 (14)0.0216 (14)
O1B0.1200 (18)0.0543 (13)0.0742 (14)0.0350 (12)0.0089 (13)0.0255 (11)
O2B0.0745 (13)0.0880 (14)0.0598 (12)0.0165 (10)0.0110 (10)0.0473 (11)
O3B0.0811 (14)0.0756 (14)0.0928 (15)0.0114 (11)0.0425 (11)0.0539 (12)
O4B0.0601 (11)0.0601 (12)0.0571 (11)0.0153 (9)0.0247 (9)0.0292 (10)
O5B0.0698 (13)0.0470 (12)0.0712 (13)0.0180 (9)0.0205 (10)0.0195 (10)
C1B0.0567 (16)0.0393 (14)0.0456 (14)0.0044 (12)0.0124 (12)0.0216 (12)
C2B0.0574 (16)0.0521 (17)0.0498 (15)0.0121 (13)0.0127 (12)0.0259 (13)
C3B0.077 (2)0.0448 (17)0.0423 (15)0.0233 (15)0.0115 (14)0.0209 (13)
C4B0.087 (2)0.0318 (14)0.0475 (15)0.0062 (14)0.0147 (14)0.0181 (12)
C5B0.085 (2)0.0359 (15)0.0640 (18)0.0115 (13)0.0187 (15)0.0198 (13)
C6B0.0659 (17)0.0435 (15)0.0635 (17)0.0000 (12)0.0224 (14)0.0296 (14)
C7B0.0410 (13)0.0439 (14)0.0420 (13)0.0017 (11)0.0055 (11)0.0231 (12)
C8B0.0364 (13)0.0408 (14)0.0418 (13)0.0040 (10)0.0039 (11)0.0170 (11)
C9B0.0474 (15)0.0333 (13)0.0571 (16)0.0012 (11)0.0036 (12)0.0159 (12)
C10B0.0506 (15)0.0328 (13)0.0555 (15)0.0050 (11)0.0046 (12)0.0183 (12)
C11B0.0449 (14)0.0441 (15)0.0557 (16)0.0093 (11)0.0047 (12)0.0311 (13)
C12B0.0448 (14)0.0596 (17)0.0492 (15)0.0032 (12)0.0000 (12)0.0371 (14)
C13B0.0572 (16)0.0500 (16)0.0398 (14)0.0022 (12)0.0044 (12)0.0221 (12)
C14B0.0573 (15)0.0356 (13)0.0432 (14)0.0049 (11)0.0048 (12)0.0186 (12)
C15B0.0576 (15)0.0322 (13)0.0359 (13)0.0025 (11)0.0117 (11)0.0168 (11)
C16B0.0684 (17)0.0353 (14)0.0434 (14)0.0009 (12)0.0131 (12)0.0187 (12)
C17B0.0476 (14)0.0344 (13)0.0363 (13)0.0016 (10)0.0049 (11)0.0163 (11)
C18B0.0486 (14)0.0382 (14)0.0410 (13)0.0008 (11)0.0070 (11)0.0208 (11)
C19B0.0391 (13)0.0315 (13)0.0400 (13)0.0030 (10)0.0033 (10)0.0159 (11)
C20B0.0376 (13)0.0339 (13)0.0429 (13)0.0004 (10)0.0014 (10)0.0162 (11)
C21B0.0413 (13)0.0318 (13)0.0397 (13)0.0002 (10)0.0035 (10)0.0186 (11)
C22B0.0366 (12)0.0343 (13)0.0456 (14)0.0033 (10)0.0018 (10)0.0206 (11)
C23B0.149 (4)0.066 (2)0.113 (3)0.026 (2)0.020 (3)0.023 (2)
C24B0.098 (3)0.120 (3)0.065 (2)0.009 (2)0.0306 (18)0.048 (2)
C25B0.0526 (16)0.0580 (18)0.0542 (16)0.0105 (13)0.0146 (13)0.0306 (15)
C26B0.0477 (15)0.0501 (17)0.0495 (15)0.0109 (13)0.0086 (12)0.0230 (14)
Geometric parameters (Å, º) top
O1—C31.362 (3)O1B—C23B1.352 (4)
O1—C231.429 (3)O1B—C3B1.379 (3)
O2—C121.368 (3)O2B—C12B1.364 (3)
O2—C241.414 (3)O2B—C24B1.418 (3)
O3—C251.192 (3)O3B—C25B1.193 (3)
O4—C251.399 (3)O4B—C26B1.397 (3)
O4—C261.401 (3)O4B—C25B1.399 (3)
O5—C261.193 (3)O5B—C26B1.194 (3)
C1—C21.374 (3)C1B—C2B1.367 (3)
C1—C151.399 (3)C1B—C15B1.398 (3)
C1—H10.9300C1B—H1B0.9300
C2—C31.386 (3)C2B—C3B1.384 (3)
C2—H20.9300C2B—H2B0.9300
C3—C41.387 (3)C3B—C4B1.376 (4)
C4—C161.391 (3)C4B—C16B1.386 (3)
C4—H40.9300C4B—H4B0.9300
C5—C161.506 (3)C5B—C16B1.497 (3)
C5—C61.518 (3)C5B—C6B1.521 (3)
C5—H5A0.9700C5B—H5C0.9700
C5—H5B0.9700C5B—H5D0.9700
C6—C181.498 (3)C6B—C18B1.508 (3)
C6—H6A0.9700C6B—H6C0.9700
C6—H6B0.9700C6B—H6D0.9700
C7—C181.378 (3)C7B—C18B1.379 (3)
C7—C81.387 (3)C7B—C8B1.391 (3)
C7—C251.478 (3)C7B—C25B1.469 (3)
C8—C201.395 (3)C8B—C20B1.385 (3)
C8—C261.474 (3)C8B—C26B1.464 (3)
C9—C201.505 (3)C9B—C20B1.506 (3)
C9—C101.518 (4)C9B—C10B1.511 (3)
C9—H9A0.9700C9B—H9C0.9700
C9—H9B0.9700C9B—H9D0.9700
C10—C221.501 (3)C10B—C22B1.493 (3)
C10—H10A0.9700C10B—H10C0.9700
C10—H10B0.9700C10B—H10D0.9700
C11—C121.379 (3)C11B—C22B1.382 (3)
C11—C221.388 (3)C11B—C12B1.389 (3)
C11—H110.9300C11B—H11B0.9300
C12—C131.378 (3)C12B—C13B1.380 (3)
C13—C141.383 (3)C13B—C14B1.385 (3)
C13—H130.9300C13B—H13B0.9300
C14—C211.389 (3)C14B—C21B1.389 (3)
C14—H140.9300C14B—H14B0.9300
C15—C161.399 (3)C15B—C16B1.400 (3)
C15—C171.480 (3)C15B—C17B1.478 (3)
C17—C181.421 (3)C17B—C18B1.413 (3)
C17—C191.427 (3)C17B—C19B1.425 (3)
C19—C201.410 (3)C19B—C20B1.410 (3)
C19—C211.488 (3)C19B—C21B1.478 (3)
C21—C221.401 (3)C21B—C22B1.406 (3)
C23—H23A0.9600C23B—H23D0.9600
C23—H23B0.9600C23B—H23E0.9600
C23—H23C0.9600C23B—H23F0.9600
C24—H24A0.9600C24B—H24D0.9600
C24—H24B0.9600C24B—H24E0.9600
C24—H24C0.9600C24B—H24F0.9600
C3—O1—C23117.74 (19)C23B—O1B—C3B118.2 (3)
C12—O2—C24118.3 (2)C12B—O2B—C24B117.4 (2)
C25—O4—C26109.91 (19)C26B—O4B—C25B109.09 (18)
C2—C1—C15121.3 (2)C2B—C1B—C15B121.2 (2)
C2—C1—H1119.4C2B—C1B—H1B119.4
C15—C1—H1119.4C15B—C1B—H1B119.4
C1—C2—C3120.5 (2)C1B—C2B—C3B119.7 (3)
C1—C2—H2119.7C1B—C2B—H2B120.2
C3—C2—H2119.7C3B—C2B—H2B120.2
O1—C3—C2116.1 (2)C4B—C3B—O1B125.0 (3)
O1—C3—C4124.7 (2)C4B—C3B—C2B120.5 (2)
C2—C3—C4119.2 (2)O1B—C3B—C2B114.5 (3)
C3—C4—C16120.4 (2)C3B—C4B—C16B120.2 (2)
C3—C4—H4119.8C3B—C4B—H4B119.9
C16—C4—H4119.8C16B—C4B—H4B119.9
C16—C5—C6109.11 (18)C16B—C5B—C6B109.4 (2)
C16—C5—H5A109.9C16B—C5B—H5C109.8
C6—C5—H5A109.9C6B—C5B—H5C109.8
C16—C5—H5B109.9C16B—C5B—H5D109.8
C6—C5—H5B109.9C6B—C5B—H5D109.8
H5A—C5—H5B108.3H5C—C5B—H5D108.2
C18—C6—C5110.95 (18)C18B—C6B—C5B110.5 (2)
C18—C6—H6A109.4C18B—C6B—H6C109.6
C5—C6—H6A109.4C5B—C6B—H6C109.6
C18—C6—H6B109.4C18B—C6B—H6D109.6
C5—C6—H6B109.4C5B—C6B—H6D109.6
H6A—C6—H6B108.0H6C—C6B—H6D108.1
C18—C7—C8122.4 (2)C18B—C7B—C8B122.1 (2)
C18—C7—C25129.9 (2)C18B—C7B—C25B130.5 (2)
C8—C7—C25107.7 (2)C8B—C7B—C25B107.4 (2)
C7—C8—C20121.9 (2)C20B—C8B—C7B122.0 (2)
C7—C8—C26108.0 (2)C20B—C8B—C26B130.1 (2)
C20—C8—C26130.0 (2)C7B—C8B—C26B107.8 (2)
C20—C9—C10109.8 (2)C20B—C9B—C10B110.35 (18)
C20—C9—H9A109.7C20B—C9B—H9C109.6
C10—C9—H9A109.7C10B—C9B—H9C109.6
C20—C9—H9B109.7C20B—C9B—H9D109.6
C10—C9—H9B109.7C10B—C9B—H9D109.6
H9A—C9—H9B108.2H9C—C9B—H9D108.1
C22—C10—C9108.9 (2)C22B—C10B—C9B110.17 (19)
C22—C10—H10A109.9C22B—C10B—H10C109.6
C9—C10—H10A109.9C9B—C10B—H10C109.6
C22—C10—H10B109.9C22B—C10B—H10D109.6
C9—C10—H10B109.9C9B—C10B—H10D109.6
H10A—C10—H10B108.3H10C—C10B—H10D108.1
C12—C11—C22121.0 (2)C22B—C11B—C12B121.1 (2)
C12—C11—H11119.5C22B—C11B—H11B119.5
C22—C11—H11119.5C12B—C11B—H11B119.5
O2—C12—C13124.7 (2)O2B—C12B—C13B125.0 (2)
O2—C12—C11115.5 (2)O2B—C12B—C11B115.1 (2)
C13—C12—C11119.9 (2)C13B—C12B—C11B119.9 (2)
C12—C13—C14119.5 (2)C12B—C13B—C14B119.1 (2)
C12—C13—H13120.2C12B—C13B—H13B120.4
C14—C13—H13120.2C14B—C13B—H13B120.4
C13—C14—C21121.7 (2)C13B—C14B—C21B122.0 (2)
C13—C14—H14119.2C13B—C14B—H14B119.0
C21—C14—H14119.2C21B—C14B—H14B119.0
C16—C15—C1117.8 (2)C1B—C15B—C16B118.5 (2)
C16—C15—C17119.52 (19)C1B—C15B—C17B121.6 (2)
C1—C15—C17122.51 (19)C16B—C15B—C17B119.1 (2)
C4—C16—C15120.6 (2)C4B—C16B—C15B119.8 (2)
C4—C16—C5121.27 (19)C4B—C16B—C5B123.0 (2)
C15—C16—C5118.1 (2)C15B—C16B—C5B117.1 (2)
C18—C17—C19119.55 (19)C18B—C17B—C19B120.04 (19)
C18—C17—C15116.29 (18)C18B—C17B—C15B116.69 (19)
C19—C17—C15124.11 (19)C19B—C17B—C15B122.9 (2)
C7—C18—C17117.29 (19)C7B—C18B—C17B117.0 (2)
C7—C18—C6123.47 (19)C7B—C18B—C6B123.7 (2)
C17—C18—C6119.24 (19)C17B—C18B—C6B119.31 (19)
C20—C19—C17120.94 (19)C20B—C19B—C17B120.2 (2)
C20—C19—C21115.84 (19)C20B—C19B—C21B117.42 (19)
C17—C19—C21123.10 (19)C17B—C19B—C21B122.36 (19)
C8—C20—C19116.6 (2)C8B—C20B—C19B116.9 (2)
C8—C20—C9123.6 (2)C8B—C20B—C9B123.6 (2)
C19—C20—C9119.8 (2)C19B—C20B—C9B119.4 (2)
C14—C21—C22118.2 (2)C14B—C21B—C22B118.2 (2)
C14—C21—C19122.64 (19)C14B—C21B—C19B123.1 (2)
C22—C21—C19118.9 (2)C22B—C21B—C19B118.56 (19)
C11—C22—C21119.6 (2)C11B—C22B—C21B119.6 (2)
C11—C22—C10122.5 (2)C11B—C22B—C10B122.5 (2)
C21—C22—C10117.8 (2)C21B—C22B—C10B117.9 (2)
O1—C23—H23A109.5O1B—C23B—H23D109.5
O1—C23—H23B109.5O1B—C23B—H23E109.5
H23A—C23—H23B109.5H23D—C23B—H23E109.5
O1—C23—H23C109.5O1B—C23B—H23F109.5
H23A—C23—H23C109.5H23D—C23B—H23F109.5
H23B—C23—H23C109.5H23E—C23B—H23F109.5
O2—C24—H24A109.5O2B—C24B—H24D109.5
O2—C24—H24B109.5O2B—C24B—H24E109.5
H24A—C24—H24B109.5H24D—C24B—H24E109.5
O2—C24—H24C109.5O2B—C24B—H24F109.5
H24A—C24—H24C109.5H24D—C24B—H24F109.5
H24B—C24—H24C109.5H24E—C24B—H24F109.5
O3—C25—O4120.1 (2)O3B—C25B—O4B120.1 (2)
O3—C25—C7132.6 (2)O3B—C25B—C7B132.1 (2)
O4—C25—C7107.2 (2)O4B—C25B—C7B107.8 (2)
O5—C26—O4120.5 (2)O5B—C26B—O4B119.8 (2)
O5—C26—C8132.3 (3)O5B—C26B—C8B132.3 (2)
O4—C26—C8107.2 (2)O4B—C26B—C8B107.9 (2)
C15—C1—C2—C30.6 (3)C15B—C1B—C2B—C3B0.2 (4)
C23—O1—C3—C2170.0 (2)C23B—O1B—C3B—C4B4.1 (4)
C23—O1—C3—C410.5 (3)C23B—O1B—C3B—C2B176.9 (3)
C1—C2—C3—O1177.3 (2)C1B—C2B—C3B—C4B1.0 (4)
C1—C2—C3—C43.2 (3)C1B—C2B—C3B—O1B179.9 (2)
O1—C3—C4—C16178.8 (2)O1B—C3B—C4B—C16B179.1 (2)
C2—C3—C4—C161.8 (3)C2B—C3B—C4B—C16B0.1 (4)
C16—C5—C6—C1855.7 (2)C16B—C5B—C6B—C18B55.4 (3)
C18—C7—C8—C205.4 (3)C18B—C7B—C8B—C20B6.9 (3)
C25—C7—C8—C20175.5 (2)C25B—C7B—C8B—C20B176.3 (2)
C18—C7—C8—C26177.6 (2)C18B—C7B—C8B—C26B174.9 (2)
C25—C7—C8—C261.5 (2)C25B—C7B—C8B—C26B1.8 (2)
C20—C9—C10—C2257.2 (3)C20B—C9B—C10B—C22B55.0 (3)
C24—O2—C12—C132.9 (4)C24B—O2B—C12B—C13B5.7 (4)
C24—O2—C12—C11175.0 (3)C24B—O2B—C12B—C11B176.7 (2)
C22—C11—C12—O2177.7 (2)C22B—C11B—C12B—O2B179.6 (2)
C22—C11—C12—C130.3 (4)C22B—C11B—C12B—C13B2.7 (3)
O2—C12—C13—C14179.0 (2)O2B—C12B—C13B—C14B179.7 (2)
C11—C12—C13—C141.2 (4)C11B—C12B—C13B—C14B2.2 (3)
C12—C13—C14—C210.1 (4)C12B—C13B—C14B—C21B1.1 (3)
C2—C1—C15—C163.4 (3)C2B—C1B—C15B—C16B2.2 (3)
C2—C1—C15—C17178.9 (2)C2B—C1B—C15B—C17B172.3 (2)
C3—C4—C16—C152.3 (3)C3B—C4B—C16B—C15B2.0 (4)
C3—C4—C16—C5175.5 (2)C3B—C4B—C16B—C5B174.2 (2)
C1—C15—C16—C44.8 (3)C1B—C15B—C16B—C4B3.1 (3)
C17—C15—C16—C4179.51 (19)C17B—C15B—C16B—C4B173.4 (2)
C1—C15—C16—C5173.1 (2)C1B—C15B—C16B—C5B173.4 (2)
C17—C15—C16—C52.6 (3)C17B—C15B—C16B—C5B3.0 (3)
C6—C5—C16—C4138.3 (2)C6B—C5B—C16B—C4B131.1 (2)
C6—C5—C16—C1539.5 (3)C6B—C5B—C16B—C15B45.2 (3)
C16—C15—C17—C1829.0 (3)C1B—C15B—C17B—C18B140.7 (2)
C1—C15—C17—C18146.5 (2)C16B—C15B—C17B—C18B29.3 (3)
C16—C15—C17—C19153.7 (2)C1B—C15B—C17B—C19B32.6 (3)
C1—C15—C17—C1930.8 (3)C16B—C15B—C17B—C19B157.3 (2)
C8—C7—C18—C172.0 (3)C8B—C7B—C18B—C17B0.7 (3)
C25—C7—C18—C17179.2 (2)C25B—C7B—C18B—C17B175.2 (2)
C8—C7—C18—C6178.1 (2)C8B—C7B—C18B—C6B178.5 (2)
C25—C7—C18—C60.7 (4)C25B—C7B—C18B—C6B2.6 (4)
C19—C17—C18—C77.2 (3)C19B—C17B—C18B—C7B11.8 (3)
C15—C17—C18—C7170.15 (19)C15B—C17B—C18B—C7B161.8 (2)
C19—C17—C18—C6172.72 (19)C19B—C17B—C18B—C6B170.2 (2)
C15—C17—C18—C69.9 (3)C15B—C17B—C18B—C6B16.2 (3)
C5—C6—C18—C7147.6 (2)C5B—C6B—C18B—C7B156.3 (2)
C5—C6—C18—C1732.4 (3)C5B—C6B—C18B—C17B25.9 (3)
C18—C17—C19—C2013.5 (3)C18B—C17B—C19B—C20B15.9 (3)
C15—C17—C19—C20163.7 (2)C15B—C17B—C19B—C20B157.3 (2)
C18—C17—C19—C21162.52 (19)C18B—C17B—C19B—C21B162.1 (2)
C15—C17—C19—C2120.3 (3)C15B—C17B—C19B—C21B24.8 (3)
C7—C8—C20—C190.6 (3)C7B—C8B—C20B—C19B2.9 (3)
C26—C8—C20—C19175.6 (2)C26B—C8B—C20B—C19B179.4 (2)
C7—C8—C20—C9179.3 (2)C7B—C8B—C20B—C9B178.8 (2)
C26—C8—C20—C93.0 (4)C26B—C8B—C20B—C9B1.1 (4)
C17—C19—C20—C89.9 (3)C17B—C19B—C20B—C8B8.3 (3)
C21—C19—C20—C8166.4 (2)C21B—C19B—C20B—C8B169.83 (19)
C17—C19—C20—C9171.4 (2)C17B—C19B—C20B—C9B170.1 (2)
C21—C19—C20—C912.3 (3)C21B—C19B—C20B—C9B11.8 (3)
C10—C9—C20—C8150.1 (2)C10B—C9B—C20B—C8B149.0 (2)
C10—C9—C20—C1931.3 (3)C10B—C9B—C20B—C19B29.3 (3)
C13—C14—C21—C222.9 (3)C13B—C14B—C21B—C22B3.8 (3)
C13—C14—C21—C19176.9 (2)C13B—C14B—C21B—C19B179.8 (2)
C20—C19—C21—C14143.3 (2)C20B—C19B—C21B—C14B148.4 (2)
C17—C19—C21—C1432.9 (3)C17B—C19B—C21B—C14B29.6 (3)
C20—C19—C21—C2230.7 (3)C20B—C19B—C21B—C22B27.5 (3)
C17—C19—C21—C22153.1 (2)C17B—C19B—C21B—C22B154.4 (2)
C12—C11—C22—C213.2 (4)C12B—C11B—C22B—C21B0.1 (3)
C12—C11—C22—C10173.5 (2)C12B—C11B—C22B—C10B179.7 (2)
C14—C21—C22—C114.4 (3)C14B—C21B—C22B—C11B3.3 (3)
C19—C21—C22—C11178.6 (2)C19B—C21B—C22B—C11B179.41 (19)
C14—C21—C22—C10172.5 (2)C14B—C21B—C22B—C10B177.1 (2)
C19—C21—C22—C101.8 (3)C19B—C21B—C22B—C10B0.9 (3)
C9—C10—C22—C11134.6 (2)C9B—C10B—C22B—C11B138.1 (2)
C9—C10—C22—C2142.2 (3)C9B—C10B—C22B—C21B42.3 (3)
C26—O4—C25—O3179.8 (2)C26B—O4B—C25B—O3B178.2 (2)
C26—O4—C25—C70.0 (2)C26B—O4B—C25B—C7B1.8 (3)
C18—C7—C25—O31.8 (4)C18B—C7B—C25B—O3B5.9 (5)
C8—C7—C25—O3179.3 (3)C8B—C7B—C25B—O3B177.7 (3)
C18—C7—C25—O4178.0 (2)C18B—C7B—C25B—O4B174.2 (2)
C8—C7—C25—O40.9 (2)C8B—C7B—C25B—O4B2.2 (3)
C25—O4—C26—O5179.9 (2)C25B—O4B—C26B—O5B179.5 (2)
C25—O4—C26—C80.9 (2)C25B—O4B—C26B—C8B0.7 (3)
C7—C8—C26—O5179.7 (3)C20B—C8B—C26B—O5B3.1 (5)
C20—C8—C26—O53.6 (5)C7B—C8B—C26B—O5B179.0 (3)
C7—C8—C26—O41.5 (3)C20B—C8B—C26B—O4B177.2 (2)
C20—C8—C26—O4175.2 (2)C7B—C8B—C26B—O4B0.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O2i0.932.583.304 (3)135
C23—H23A···O3Bii0.962.713.666 (3)177
C6B—H6D···O3Biii0.972.683.547 (3)149
C10B—H10C···O5Biv0.972.443.297 (3)147
C13B—H13B···O5v0.932.563.408 (3)152
C24B—H24D···O1Bv0.962.743.491 (4)136
Symmetry codes: (i) x, y, z; (ii) x1, y1, z; (iii) x+2, y+1, z+1; (iv) x+2, y, z+1; (v) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O2i0.932.583.304 (3)134.9
C23—H23A···O3Bii0.962.713.666 (3)177.0
C6B—H6D···O3Biii0.972.683.547 (3)148.8
C10B—H10C···O5Biv0.972.443.297 (3)147.3
C13B—H13B···O5v0.932.563.408 (3)152.2
C24B—H24D···O1Bv0.962.743.491 (4)135.8
Symmetry codes: (i) x, y, z; (ii) x1, y1, z; (iii) x+2, y+1, z+1; (iv) x+2, y, z+1; (v) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC26H20O5
Mr412.42
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)8.7570 (9), 15.9008 (16), 16.2987 (16)
α, β, γ (°)61.695 (3), 84.535 (3), 84.460 (3)
V3)1985.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.42 × 0.34 × 0.16
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2012)
Tmin, Tmax0.67, 0.75
No. of measured, independent and
observed [I > 2σ(I)] reflections
33986, 7072, 4457
Rint0.049
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.140, 1.02
No. of reflections7072
No. of parameters559
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.55, 0.28

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2013), SHELXS2013 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

 

Acknowledgements

This research was supported by the National Metal and Materials Technology Center, MTEC (grant Nos. MT—B-55-POL-07–522-I and MT—B55-POL-07–523-I).

References

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