supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, o2448    [ doi:10.1107/S1600536809035922 ]

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

C. Lian, P. Lu and Y. Zhu

Abstract top

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.

Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. palladium(II) chloride catalyzed synthesis of the title compound.
[Figure 2] Fig. 2. View of the title compound showing the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level.
[Figure 3] Fig. 3. The perspective packing view of the titie compound.
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 top
Crystal data top
C30H26Br2O4·C2H6OF(000) = 1336
Mr = 656.40Dx = 1.512 Mg m−3
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 mm−1
c = 18.740 (3) ÅT = 298 K
V = 2883.2 (7) Å3Block, red
Z = 40.26 × 0.18 × 0.12 mm
Data collection top
Bruker APEXII area-detector
diffractometer		5155 independent reflections
Radiation source: fine-focus sealed tube3685 reflections with I > 2σ(I)
graphiteRint = 0.041
φ 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 top
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) = 0.078 w = 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 Å−3
357 parametersΔρmin = −0.27 e Å−3
1 restraintAbsolute structure: Flack (1983), 2379 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.020 (8)
Crystal data top
C30H26Br2O4·C2H6OV = 2883.2 (7) Å3
Mr = 656.40Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 15.016 (2) ŵ = 2.85 mm−1
b = 10.2459 (14) ÅT = 298 K
c = 18.740 (3) Å0.26 × 0.18 × 0.12 mm
Data collection top
Bruker APEXII area-detector
diffractometer		5155 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		3685 reflections with I > 2σ(I)
Tmin = 0.546, Tmax = 0.710Rint = 0.041
14442 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.078Δρmax = 0.33 e Å−3
S = 1.00Δρmin = −0.27 e Å−3
5155 reflectionsAbsolute structure: Flack (1983), 2379 Friedel pairs
357 parametersFlack parameter: 0.020 (8)
1 restraint
Special details top

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) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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

references
References top

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.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Wang, X., Shi, D., Li, Y., Chen, H., Wei, X. & Zong, Z. (2005). Synth. Commun. 35, 97–104.