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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2448.
Published online 2009 September 12. doi:  10.1107/S1600536809035922
PMCID: PMC2970291

7-Bromo-4-(7-bromo-3,3-dimethyl-1-oxo-2,3,4,9-tetra­hydro-1H-xanthen-9-yl)-3,3-dimethyl-2,3-dihydroxanthen-1(4H)-one ethanol solvate

Abstract

The title compound, C30H26Br2O4·C2H5OH, was synthesized from the reaction between 5-bromo­salicybenzaldehyde and 5,5-dimethyl-1,3-cyclo­hexa­nedione. The crystal packing is stabilized by inter­molecular O—H(...)O hydrogen bonds and C—H(...)O inter­actions.

Related literature

For the properties and applications of xanthenes, see: Gusak et al. (2000 [triangle]); Sato et al. (2008 [triangle]); Wang et al. (2005 [triangle]).

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Object name is e-65-o2448-scheme1.jpg

Experimental

Crystal data

  • C30H26Br2O4·C2H6O
  • M r = 656.40
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2448-efi1.jpg
  • a = 15.016 (2) Å
  • b = 10.2459 (14) Å
  • c = 18.740 (3) Å
  • V = 2883.2 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.85 mm−1
  • T = 298 K
  • 0.26 × 0.18 × 0.12 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2004 [triangle]) T min = 0.546, T max = 0.710
  • 14442 measured reflections
  • 5155 independent reflections
  • 3685 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.078
  • S = 1.01
  • 5155 reflections
  • 357 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.27 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2379 Friedel pairs
  • Flack parameter: 0.020 (8)

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035922/jh2097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035922/jh2097Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank South China Normal University for financial support (grant Nos. SCNU033038 and SCNU524002).

supplementary crystallographic information

Comment

Organic molecules containing xanthene are of biological importance and useful in drug discovery. They are also very efficient laser dyes and outstanding photophysical properties. (Gusak et al., 2000; Sato et al., 2008; Wang et al., 2005). As one part of our on going studies on the synthesis of xanthene-containing heterocyclic compounds, the title compound was isolated unexpectedly.

The reaction between 5-bromosalicybenzaldehyde and 5,5-dimethyl-1,3-cyclohexanedione proceeded to give the title compound in excellent yield in the presence of palladium(II) chloride as catalyst in acetonitrile under reflux (Figure 1). The structure of the title compound is illustrated in Figure 2. There are no unusual bond lengths and angles in the compound. The phenyl rings show no interactions in the crystal. The compound contains two similar linked rings: a pyranoid ring connected two six-membered rings, the structure about two big rings connected each other via C3—C23 bond. The two big rings are approximately planar (Figure 3). In addition, the molecule is connected with the ethanol molecule by O(5)—H(5)···O(1) and interior C(14)—H(14)···O(3), which is less than the sum of their van der Waals.

Experimental

A mixture of 5-bromosalicybenzaldehyde (1.00g, 5mmol), 5,5-dimethyl-1,3-cyclohexanedione (1.12 g, 10 mmol), thiourea (0.76 g, 10 mmol), and palladium(II) chloride was refluxed in acetonitrile (12 ml) at 298 K for 12 h. After being cooled to room temperature, The red precipitation was filtered through a silica pad, and then washed twice with water, dried under vacuum to yield the product. Single crystal of the title compound was obtained by slow evaporation from ethanol at room temperature. The compound is isolated as red, block-shaped crystal from ethanol at room temperature.

Refinement

The H atoms were positioned geometrically and allowed to ride on their parentatoms, with C—H = 0.93–0.97 Å, and O—H = 0.82 Å and Uiso = 1.2 or 1.5 Ueq(parent atom).

Figures

Fig. 1.
palladium(II) chloride catalyzed synthesis of the title compound.
Fig. 2.
View of the title compound showing the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level.
Fig. 3.
The perspective packing view of the titie compound.

Crystal data

C30H26Br2O4·C2H6OF(000) = 1336
Mr = 656.40Dx = 1.512 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 3559 reflections
a = 15.016 (2) Åθ = 2.2–21.8°
b = 10.2459 (14) ŵ = 2.85 mm1
c = 18.740 (3) ÅT = 298 K
V = 2883.2 (7) Å3Block, red
Z = 40.26 × 0.18 × 0.12 mm

Data collection

Bruker APEXII area-detector diffractometer5155 independent reflections
Radiation source: fine-focus sealed tube3685 reflections with I > 2σ(I)
graphiteRint = 0.041
[var phi] and ω scanθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −18→17
Tmin = 0.546, Tmax = 0.710k = −11→12
14442 measured reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.078w = 1/[σ2(Fo2) + (0.016P)2 + 0.6332P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
5155 reflectionsΔρmax = 0.33 e Å3
357 parametersΔρmin = −0.27 e Å3
1 restraintAbsolute structure: Flack (1983), 2379 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.020 (8)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/Ueq
Br10.42195 (3)0.14209 (5)0.41954 (3)0.06989 (17)
Br20.62250 (4)1.02446 (4)0.12373 (4)0.07602 (18)
C90.5865 (3)0.3725 (4)0.2527 (2)0.0339 (10)
C20.5465 (3)0.3620 (4)0.1083 (2)0.0343 (9)
C80.5154 (3)0.2968 (4)0.2299 (2)0.0352 (9)
C30.6267 (2)0.4279 (3)0.1314 (2)0.0332 (9)
C40.6893 (3)0.4756 (4)0.08862 (18)0.0297 (9)
C60.5783 (3)0.4647 (5)−0.0097 (2)0.0475 (11)
H6A0.55900.5534−0.00030.057*
H6B0.57010.4480−0.06020.057*
C70.4942 (3)0.2991 (4)0.1543 (2)0.0368 (10)
H70.44360.25620.13780.044*
C50.6777 (3)0.4528 (4)0.00836 (18)0.0380 (10)
C120.4897 (3)0.2371 (4)0.3510 (2)0.0468 (11)
C130.4668 (3)0.2280 (4)0.2804 (2)0.0427 (10)
H130.41900.17610.26640.051*
C110.5580 (3)0.3144 (5)0.3737 (2)0.0483 (12)
H110.57170.32050.42190.058*
C10.5220 (3)0.3733 (4)0.0316 (2)0.0452 (11)
C100.6068 (3)0.3839 (4)0.3235 (2)0.0451 (11)
H100.65310.43810.33800.054*
O10.4611 (3)0.3130 (4)0.00624 (17)0.0721 (10)
C140.7095 (3)0.3150 (4)−0.0113 (2)0.0480 (11)
H14A0.67410.25160.01360.072*
H14B0.77080.30510.00210.072*
H14C0.70340.3021−0.06180.072*
C150.7300 (3)0.5510 (4)−0.0373 (2)0.0512 (12)
H15A0.71180.5435−0.08620.077*
H15B0.79260.5329−0.03350.077*
H15C0.71840.6379−0.02060.077*
O20.63770 (16)0.4421 (3)0.20540 (13)0.0380 (7)
C210.8334 (3)0.4733 (4)0.2348 (2)0.0333 (9)
C240.7435 (3)0.6669 (4)0.1613 (2)0.0339 (9)
C170.8935 (3)0.3742 (4)0.1292 (2)0.0381 (9)
C230.7709 (2)0.5480 (3)0.1187 (2)0.0324 (8)
H230.80620.57870.07800.039*
C280.6787 (3)0.8803 (4)0.1690 (3)0.0462 (11)
C290.7040 (2)0.7750 (4)0.1286 (2)0.0440 (10)
H290.69490.77550.07960.053*
C220.8303 (3)0.4641 (4)0.1636 (2)0.0320 (9)
C250.7517 (3)0.6708 (4)0.2340 (2)0.0360 (9)
C270.6889 (3)0.8824 (4)0.2422 (3)0.0515 (12)
H270.67100.95460.26870.062*
C260.7258 (3)0.7757 (4)0.2750 (2)0.0417 (10)
H260.73330.77430.32430.050*
C200.8834 (3)0.3859 (4)0.2829 (2)0.0431 (11)
H20A0.84750.36860.32490.052*
H20B0.93720.43010.29840.052*
C190.9089 (3)0.2562 (4)0.2483 (2)0.0452 (11)
C180.9498 (3)0.2880 (4)0.1766 (2)0.0465 (11)
H18A1.00660.33070.18440.056*
H18B0.96150.20680.15160.056*
O30.9023 (2)0.3738 (3)0.06442 (16)0.0526 (8)
O40.78986 (17)0.5671 (3)0.27188 (12)0.0382 (7)
C300.9769 (4)0.1859 (5)0.2962 (3)0.0721 (15)
H30A0.99360.10460.27460.108*
H30B0.95080.16960.34210.108*
H30C1.02880.23970.30180.108*
C310.8274 (4)0.1713 (5)0.2391 (3)0.0683 (14)
H31A0.78360.21730.21150.102*
H31B0.80320.15030.28510.102*
H31C0.84370.09230.21480.102*
O50.6800 (4)0.8520 (6)0.4501 (3)0.169 (3)
H50.63330.81180.45570.253*
C330.6290 (5)1.0123 (7)0.5278 (4)0.113 (2)
H33A0.63040.93390.55580.170*
H33B0.56881.04280.52390.170*
H33C0.66481.07800.55040.170*
C320.6640 (6)0.9856 (7)0.4571 (5)0.121 (3)
H32A0.62151.01370.42120.145*
H32B0.71891.03370.44990.145*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0664 (3)0.0769 (4)0.0663 (3)−0.0076 (3)0.0261 (3)0.0185 (3)
Br20.0842 (4)0.0433 (3)0.1006 (4)0.0189 (3)−0.0024 (3)0.0077 (3)
C90.028 (2)0.037 (2)0.037 (2)0.0032 (19)0.0031 (18)0.001 (2)
C20.034 (2)0.036 (2)0.033 (2)0.0049 (18)−0.0022 (18)−0.0084 (19)
C80.025 (2)0.040 (2)0.040 (2)0.0040 (18)0.0026 (18)0.0015 (19)
C30.037 (2)0.036 (2)0.027 (2)0.0033 (17)−0.0050 (18)−0.002 (2)
C40.034 (2)0.027 (2)0.0283 (19)0.0044 (18)−0.0014 (17)0.0016 (16)
C60.053 (3)0.060 (3)0.029 (2)0.014 (2)−0.010 (2)−0.002 (2)
C70.032 (2)0.035 (2)0.044 (2)0.0044 (18)−0.0063 (19)−0.0096 (18)
C50.049 (3)0.040 (3)0.025 (2)0.007 (2)−0.0034 (18)−0.0027 (17)
C120.040 (3)0.055 (3)0.046 (3)0.000 (2)0.015 (2)0.009 (2)
C130.031 (2)0.046 (3)0.052 (3)0.002 (2)0.003 (2)−0.001 (2)
C110.044 (3)0.071 (3)0.029 (2)0.002 (2)0.003 (2)0.002 (2)
C10.041 (3)0.052 (3)0.043 (2)0.005 (2)−0.010 (2)−0.011 (2)
C100.038 (3)0.060 (3)0.038 (2)−0.006 (2)0.0007 (19)−0.001 (2)
O10.070 (2)0.088 (3)0.058 (2)−0.022 (2)−0.0222 (18)−0.0086 (19)
C140.061 (3)0.050 (3)0.033 (2)0.011 (2)−0.003 (2)−0.006 (2)
C150.069 (4)0.058 (3)0.026 (2)0.001 (2)0.001 (2)0.002 (2)
O20.0399 (17)0.0495 (17)0.0245 (13)−0.0103 (13)0.0010 (13)−0.0024 (13)
C210.028 (2)0.040 (2)0.031 (2)−0.0013 (19)0.0027 (18)−0.0038 (19)
C240.030 (2)0.036 (2)0.036 (2)−0.0031 (19)0.0044 (17)0.000 (2)
C170.034 (2)0.042 (2)0.039 (2)−0.0026 (17)0.0072 (19)−0.004 (2)
C230.032 (2)0.040 (2)0.0245 (18)−0.0007 (16)0.0041 (18)0.001 (2)
C280.042 (3)0.032 (2)0.065 (3)0.005 (2)0.004 (2)0.001 (2)
C290.047 (3)0.042 (2)0.043 (2)−0.0034 (19)0.004 (2)0.000 (2)
C220.027 (2)0.035 (2)0.034 (2)0.0000 (18)0.0043 (17)0.0004 (18)
C250.034 (2)0.034 (2)0.040 (2)−0.0039 (18)−0.0020 (19)−0.003 (2)
C270.046 (3)0.043 (3)0.065 (3)−0.004 (2)0.009 (2)−0.020 (2)
C260.040 (3)0.045 (3)0.040 (2)−0.005 (2)0.0067 (19)−0.012 (2)
C200.037 (2)0.054 (3)0.039 (2)−0.003 (2)−0.0022 (19)0.011 (2)
C190.034 (3)0.045 (3)0.056 (3)0.001 (2)−0.005 (2)0.011 (2)
C180.037 (3)0.050 (3)0.052 (3)0.007 (2)0.000 (2)0.004 (2)
O30.051 (2)0.064 (2)0.0423 (19)0.0083 (15)0.0145 (14)−0.0049 (15)
O40.0409 (18)0.0456 (17)0.0281 (14)0.0005 (14)0.0014 (12)−0.0047 (13)
C300.065 (4)0.082 (4)0.070 (3)0.022 (3)−0.004 (3)0.021 (3)
C310.065 (4)0.050 (3)0.091 (4)−0.014 (3)0.004 (3)0.010 (3)
O50.164 (5)0.141 (5)0.200 (7)−0.022 (4)0.093 (5)−0.032 (4)
C330.128 (7)0.107 (6)0.105 (5)0.011 (5)0.003 (5)−0.029 (4)
C320.129 (6)0.065 (5)0.169 (8)0.023 (4)0.035 (5)−0.014 (5)

Geometric parameters (Å, °)

Br1—C121.906 (4)C24—C291.398 (5)
Br2—C281.901 (4)C24—C231.514 (5)
C9—C101.366 (6)C17—O31.221 (5)
C9—O21.374 (5)C17—C221.471 (5)
C9—C81.387 (5)C17—C181.512 (6)
C2—C71.332 (5)C23—C221.498 (5)
C2—C31.447 (5)C23—H230.9800
C2—C11.488 (6)C28—C291.371 (5)
C8—C131.388 (5)C28—C271.381 (6)
C8—C71.453 (5)C29—H290.9300
C3—C41.328 (5)C25—C261.377 (5)
C3—O21.404 (4)C25—O41.401 (5)
C4—C51.532 (5)C27—C261.371 (6)
C4—C231.540 (5)C27—H270.9300
C6—C11.481 (6)C26—H260.9300
C6—C51.535 (6)C20—C191.527 (6)
C6—H6A0.9700C20—H20A0.9700
C6—H6B0.9700C20—H20B0.9700
C7—H70.9300C19—C311.512 (6)
C5—C141.535 (6)C19—C181.513 (6)
C5—C151.537 (6)C19—C301.539 (6)
C12—C111.364 (6)C18—H18A0.9700
C12—C131.371 (6)C18—H18B0.9700
C13—H130.9300C30—H30A0.9600
C11—C101.388 (6)C30—H30B0.9600
C11—H110.9300C30—H30C0.9600
C1—O11.202 (5)C31—H31A0.9600
C10—H100.9300C31—H31B0.9600
C14—H14A0.9600C31—H31C0.9600
C14—H14B0.9600O5—C321.397 (8)
C14—H14C0.9600O5—H50.8200
C15—H15A0.9600C33—C321.451 (10)
C15—H15B0.9600C33—H33A0.9600
C15—H15C0.9600C33—H33B0.9600
C21—C221.338 (5)C33—H33C0.9600
C21—O41.354 (5)C32—H32A0.9700
C21—C201.476 (5)C32—H32B0.9700
C24—C251.368 (6)
C10—C9—O2117.2 (4)C22—C23—C4113.8 (3)
C10—C9—C8121.3 (4)C24—C23—C4111.4 (3)
O2—C9—C8121.4 (3)C22—C23—H23107.4
C7—C2—C3121.6 (3)C24—C23—H23107.4
C7—C2—C1121.1 (4)C4—C23—H23107.4
C3—C2—C1117.2 (4)C29—C28—C27122.0 (4)
C9—C8—C13118.6 (4)C29—C28—Br2119.3 (3)
C9—C8—C7117.5 (4)C27—C28—Br2118.7 (3)
C13—C8—C7123.9 (4)C28—C29—C24120.0 (4)
C4—C3—O2118.3 (3)C28—C29—H29120.0
C4—C3—C2125.5 (3)C24—C29—H29120.0
O2—C3—C2116.2 (3)C21—C22—C17117.4 (4)
C3—C4—C5117.1 (3)C21—C22—C23122.7 (4)
C3—C4—C23121.3 (3)C17—C22—C23119.8 (3)
C5—C4—C23121.6 (3)C24—C25—C26123.6 (4)
C1—C6—C5112.9 (3)C24—C25—O4121.3 (4)
C1—C6—H6A109.0C26—C25—O4115.1 (3)
C5—C6—H6A109.0C26—C27—C28118.6 (4)
C1—C6—H6B109.0C26—C27—H27120.7
C5—C6—H6B109.0C28—C27—H27120.7
H6A—C6—H6B107.8C27—C26—C25119.0 (4)
C2—C7—C8120.6 (4)C27—C26—H26120.5
C2—C7—H7119.7C25—C26—H26120.5
C8—C7—H7119.7C21—C20—C19113.4 (3)
C4—C5—C6108.4 (3)C21—C20—H20A108.9
C4—C5—C14109.9 (3)C19—C20—H20A108.9
C6—C5—C14108.8 (3)C21—C20—H20B108.9
C4—C5—C15112.9 (3)C19—C20—H20B108.9
C6—C5—C15108.8 (3)H20A—C20—H20B107.7
C14—C5—C15108.0 (3)C31—C19—C18110.5 (4)
C11—C12—C13121.9 (4)C31—C19—C20110.3 (4)
C11—C12—Br1119.3 (3)C18—C19—C20107.0 (3)
C13—C12—Br1118.8 (3)C31—C19—C30109.5 (4)
C12—C13—C8119.5 (4)C18—C19—C30110.5 (4)
C12—C13—H13120.3C20—C19—C30109.1 (4)
C8—C13—H13120.3C17—C18—C19114.9 (3)
C12—C11—C10119.0 (4)C17—C18—H18A108.6
C12—C11—H11120.5C19—C18—H18A108.6
C10—C11—H11120.5C17—C18—H18B108.6
O1—C1—C6123.5 (4)C19—C18—H18B108.6
O1—C1—C2122.0 (4)H18A—C18—H18B107.5
C6—C1—C2114.5 (4)C21—O4—C25118.4 (3)
C9—C10—C11119.7 (4)C19—C30—H30A109.5
C9—C10—H10120.2C19—C30—H30B109.5
C11—C10—H10120.2H30A—C30—H30B109.5
C5—C14—H14A109.5C19—C30—H30C109.5
C5—C14—H14B109.5H30A—C30—H30C109.5
H14A—C14—H14B109.5H30B—C30—H30C109.5
C5—C14—H14C109.5C19—C31—H31A109.5
H14A—C14—H14C109.5C19—C31—H31B109.5
H14B—C14—H14C109.5H31A—C31—H31B109.5
C5—C15—H15A109.5C19—C31—H31C109.5
C5—C15—H15B109.5H31A—C31—H31C109.5
H15A—C15—H15B109.5H31B—C31—H31C109.5
C5—C15—H15C109.5C32—O5—H5109.5
H15A—C15—H15C109.5C32—C33—H33A109.5
H15B—C15—H15C109.5C32—C33—H33B109.5
C9—O2—C3121.2 (3)H33A—C33—H33B109.5
C22—C21—O4123.1 (4)C32—C33—H33C109.5
C22—C21—C20125.6 (4)H33A—C33—H33C109.5
O4—C21—C20111.3 (3)H33B—C33—H33C109.5
C25—C24—C29116.8 (4)O5—C32—C33109.4 (6)
C25—C24—C23121.6 (3)O5—C32—H32A109.8
C29—C24—C23121.5 (4)C33—C32—H32A109.8
O3—C17—C22120.6 (4)O5—C32—H32B109.8
O3—C17—C18121.4 (4)C33—C32—H32B109.8
C22—C17—C18118.0 (4)H32A—C32—H32B108.2
C22—C23—C24109.1 (3)
C10—C9—C8—C13−2.4 (6)C25—C24—C23—C4109.0 (4)
O2—C9—C8—C13179.5 (3)C29—C24—C23—C4−67.3 (5)
C10—C9—C8—C7174.9 (4)C3—C4—C23—C2264.4 (5)
O2—C9—C8—C7−3.1 (6)C5—C4—C23—C22−114.3 (4)
C7—C2—C3—C4169.2 (4)C3—C4—C23—C24−59.5 (5)
C1—C2—C3—C4−14.0 (6)C5—C4—C23—C24121.9 (4)
C7—C2—C3—O2−11.2 (5)C27—C28—C29—C24−1.7 (6)
C1—C2—C3—O2165.6 (3)Br2—C28—C29—C24−178.5 (3)
O2—C3—C4—C5177.2 (3)C25—C24—C29—C282.5 (6)
C2—C3—C4—C5−3.2 (6)C23—C24—C29—C28179.0 (4)
O2—C3—C4—C23−1.6 (5)O4—C21—C22—C17168.7 (3)
C2—C3—C4—C23178.1 (3)C20—C21—C22—C17−11.0 (6)
C3—C2—C7—C81.2 (6)O4—C21—C22—C23−6.6 (6)
C1—C2—C7—C8−175.5 (4)C20—C21—C22—C23173.7 (4)
C9—C8—C7—C26.2 (6)O3—C17—C22—C21−170.3 (4)
C13—C8—C7—C2−176.6 (4)C18—C17—C22—C216.7 (5)
C3—C4—C5—C637.6 (5)O3—C17—C22—C235.1 (6)
C23—C4—C5—C6−143.6 (3)C18—C17—C22—C23−177.9 (3)
C3—C4—C5—C14−81.2 (4)C24—C23—C22—C2119.4 (5)
C23—C4—C5—C1497.5 (4)C4—C23—C22—C21−105.7 (4)
C3—C4—C5—C15158.2 (4)C24—C23—C22—C17−155.8 (3)
C23—C4—C5—C15−23.0 (5)C4—C23—C22—C1779.1 (4)
C1—C6—C5—C4−57.1 (4)C29—C24—C25—C26−2.1 (6)
C1—C6—C5—C1462.4 (4)C23—C24—C25—C26−178.5 (4)
C1—C6—C5—C15179.9 (3)C29—C24—C25—O4179.7 (3)
C11—C12—C13—C81.5 (7)C23—C24—C25—O43.2 (6)
Br1—C12—C13—C8179.9 (3)C29—C28—C27—C260.3 (7)
C9—C8—C13—C120.3 (6)Br2—C28—C27—C26177.1 (3)
C7—C8—C13—C12−176.9 (4)C28—C27—C26—C250.2 (6)
C13—C12—C11—C10−1.2 (7)C24—C25—C26—C270.8 (6)
Br1—C12—C11—C10−179.7 (3)O4—C25—C26—C27179.1 (4)
C5—C6—C1—O1−138.1 (4)C22—C21—C20—C19−18.5 (6)
C5—C6—C1—C242.3 (5)O4—C21—C20—C19161.8 (3)
C7—C2—C1—O1−9.7 (6)C21—C20—C19—C31−71.7 (5)
C3—C2—C1—O1173.5 (4)C21—C20—C19—C1848.5 (4)
C7—C2—C1—C6169.9 (4)C21—C20—C19—C30168.0 (4)
C3—C2—C1—C6−6.9 (5)O3—C17—C18—C19−156.0 (4)
O2—C9—C10—C11−179.1 (4)C22—C17—C18—C1927.0 (5)
C8—C9—C10—C112.7 (6)C31—C19—C18—C1767.1 (5)
C12—C11—C10—C9−0.9 (7)C20—C19—C18—C17−53.0 (5)
C10—C9—O2—C3174.5 (3)C30—C19—C18—C17−171.6 (4)
C8—C9—O2—C3−7.3 (5)C22—C21—O4—C25−10.4 (6)
C4—C3—O2—C9−166.1 (3)C20—C21—O4—C25169.3 (3)
C2—C3—O2—C914.2 (5)C24—C25—O4—C2111.9 (5)
C25—C24—C23—C22−17.4 (5)C26—C25—O4—C21−166.5 (3)
C29—C24—C23—C22166.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C14—H14B···O30.962.403.280 (6)152
O5—H5···O1i0.822.132.908 (7)158

Symmetry codes: (i) −x+1, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2097).

References

  • Bruker (2004). SADABS, SAINT and APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Gusak, K. N., Tereshko, A. B., Kozlov, N. G. & Shakailo, N. I. (2000). Russ. J. Gen. Chem.70, 1793–1800.
  • Sato, N., Jitsuoka, M., Shibata, T., Hirohashi, T., Nonoshita, K., Moriya, M., Haga, Y., Sakuraba, A., Ando, M., Ohe, T., Iwaasa, H., Gomori, A., Ishihara, A., Kanatani, A. & Fukami, T. (2008). J. Med. Chem.51, 4765–4770. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, X., Shi, D., Li, Y., Chen, H., Wei, X. & Zong, Z. (2005). Synth. Commun.35, 97–104.

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