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

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ISSN: 2056-9890

3,28-Diacet­­oxy-29-bromo­betulin

aCollege of Life Sciences, Northeast Forestry University, Harbin 150040, People's Republic of China, and bSchool of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150080, People's Republic of China
*Correspondence e-mail: xiufeng.yan@126.com

(Received 2 July 2009; accepted 14 July 2009; online 25 July 2009)

In the title mol­ecule, C34H53BrO4, all the cyclo­hexane rings adopt chair conformations, while the cyclo­pentane ring adopts an envelope conformation. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into corrugated sheets parallel to the ab plane.

Related literature

For the anti-HIV and anti­tumor activities of betulin derivatives, see: Sun et al. (1998[Sun, C.-I., Wang, H.-K., Kashiwada, Y., Shen, J.-K., Cosentino, L.-M., Chen, C.-H., Yang, L.-M. & Lee, K.-H. (1998). J. Med. Chem. 41, 4648-4657.]) and Kim et al. (1998[Kim, D. S., Pezzuto, J. M. & Pisha, E. (1998). Bioorg. Med. Chem. Lett. 8, 1707-1712.]), respectively. For a related structure, see Mohamed et al. (2006[Mohamed, I. E., Choudhary, M. I., Ali, S., Anjum, S. & Atta-ur-Rahman (2006). Acta Cryst. E62, o1352-o1354.]).

[Scheme 1]

Experimental

Crystal data
  • C34H53BrO4

  • Mr = 605.67

  • Orthorhombic, P 21 21 21

  • a = 7.152 (3) Å

  • b = 14.946 (7) Å

  • c = 29.837 (12) Å

  • V = 3189 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.32 mm−1

  • T = 291 K

  • 0.40 × 0.38 × 0.37 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.622, Tmax = 0.642

  • 23319 measured reflections

  • 5578 independent reflections

  • 3534 reflections with I > 2σ(I)

  • Rint = 0.102

Refinement
  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.145

  • S = 0.94

  • 5578 reflections

  • 358 parameters

  • 18 restraints

  • H-atom parameters constrained

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.58 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2346 Friedel pairs

  • Flack parameter: 0.024 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C32—H32A⋯O4i 0.96 2.48 3.365 (7) 154
C28—H28B⋯O4ii 0.97 2.57 3.487 (6) 158
Symmetry codes: (i) x+1, y-1, z; (ii) x, y-1, z.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Betulin and its derivatives have been attracting extensive interests, owing to their anti-HIV and antitumor activites (Sun et al., 1998; Kim et al., 1998). The crystal structure of the diacetylation of betulin has been reported, considering the significance of its stereochemistry study. (Mohamed et al., 2006). We report here the synthesis and the crystal structure of the title compound (I) - a new betulin derivative.

In (I) (Fig. 1), the cyclopentane ring adopts a twisted envelope conformation and all cyclohexane rings adopt chair conformations. The bond distances and angles are all within the expected ranges and agree with those in the similar compound reported previously (Mohamed et al., 2006).

In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into corrugated sheets parallel to ab plane.

Related literature top

For the anti-HIV and antitumor activities of betulin derivatives, see: Sun et al. (1998) and Kim et al. (1998), respectively. For a related structure, see Mohamed et al. (2006).

Experimental top

Purified betulin (4.4 g, 10 mmol) was dissolved in dichloromethane (100 ml) and pyridine (0.5 ml) mixed solvent, followed by the addition of acetic anhydride (5 ml, 5.3 mmol). The reaction mixture was stirred for 24 h at room temperature. The solvent was removed by distillation under vacuum. The crude product was washed with a small quantity of benzene and then recrystallized from benzene (30 ml), 3.1 g diacetate-betulin was obtained.

The 3, 28-diacetate-betulin (1.0 g, 2 mmol), N-bromosuccinimide (0.35 g, 2 mmol) and benzoyl peroxide (0.05 g, 0.22 mmol) were dissolved in tetrachloromethane (50 ml). The reaction mixture was stirred for 6 h at reflux temperature. The solvent was removed by distillation under vacuum. The crude product was washed with a small quantity of ethanol and then recrystallized from petroleum ether (6 ml), 0.4 g suitable for X-ray diffraction test colourless block crystals of the titel compound was obtained.

Refinement top

C-bound H-atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.96-0.98 Å and Uiso(H) = 1.2-1.5Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. A portion of the crystal, showing the two-dimensional sheet of hydrogen-bonded (dashed lines) molecules. H atoms not involved in hydrogen bonds have been omitted.
3,28-Diacetoxy-29-bromobetulin top
Crystal data top
C34H53BrO4F(000) = 1296
Mr = 605.67Dx = 1.261 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 15343 reflections
a = 7.152 (3) Åθ = 3.1–27.4°
b = 14.946 (7) ŵ = 1.32 mm1
c = 29.837 (12) ÅT = 291 K
V = 3189 (2) Å3Block, colourless
Z = 40.40 × 0.38 × 0.37 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5578 independent reflections
Radiation source: fine-focus sealed tube3534 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.102
ω scansθmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 88
Tmin = 0.622, Tmax = 0.642k = 1717
23319 measured reflectionsl = 3535
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)] = 0.057H-atom parameters constrained
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.066P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max < 0.001
5578 reflectionsΔρmax = 0.45 e Å3
358 parametersΔρmin = 0.58 e Å3
18 restraintsAbsolute structure: Flack (1983), 2346 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.024 (12)
Crystal data top
C34H53BrO4V = 3189 (2) Å3
Mr = 605.67Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.152 (3) ŵ = 1.32 mm1
b = 14.946 (7) ÅT = 291 K
c = 29.837 (12) Å0.40 × 0.38 × 0.37 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5578 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
3534 reflections with I > 2σ(I)
Tmin = 0.622, Tmax = 0.642Rint = 0.102
23319 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.145Δρmax = 0.45 e Å3
S = 0.94Δρmin = 0.58 e Å3
5578 reflectionsAbsolute structure: Flack (1983), 2346 Friedel pairs
358 parametersAbsolute structure parameter: 0.024 (12)
18 restraints
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br11.44746 (8)0.01367 (6)0.18762 (2)0.1130 (4)
C11.0979 (5)0.4597 (3)0.38899 (13)0.0394 (10)
H1A1.22510.44680.37980.047*
H1B1.02390.46850.36210.047*
C21.0967 (5)0.5466 (3)0.41652 (14)0.0419 (10)
H2A1.17800.54010.44230.050*
H2B1.14370.59550.39840.050*
C30.9011 (6)0.5672 (3)0.43183 (13)0.0384 (10)
H30.82150.57440.40530.046*
C40.8156 (5)0.4940 (3)0.46193 (12)0.0366 (9)
C50.8272 (5)0.4054 (3)0.43421 (12)0.0311 (9)
H50.74950.41690.40780.037*
C60.7341 (6)0.3239 (3)0.45702 (14)0.0430 (11)
H6A0.81620.30060.48010.052*
H6B0.61820.34240.47120.052*
C70.6935 (5)0.2506 (3)0.42254 (13)0.0380 (10)
H7A0.60440.27330.40080.046*
H7B0.63600.20020.43770.046*
C80.8677 (5)0.2177 (3)0.39760 (12)0.0308 (9)
C90.9820 (4)0.3005 (3)0.37983 (11)0.0294 (8)
H90.90090.32760.35710.035*
C101.0203 (4)0.3785 (3)0.41474 (11)0.0281 (8)
C111.1536 (5)0.2692 (3)0.35383 (13)0.0379 (10)
H11A1.23950.24040.37440.045*
H11B1.21640.32110.34130.045*
C121.1069 (5)0.2039 (3)0.31566 (13)0.0367 (9)
H12A1.03730.23540.29260.044*
H12B1.22230.18250.30240.044*
C130.9924 (5)0.1240 (3)0.33177 (12)0.0310 (9)
H131.06810.09340.35440.037*
C140.8095 (5)0.1562 (3)0.35600 (12)0.0324 (9)
C150.6922 (6)0.0744 (3)0.37207 (14)0.0445 (11)
H15A0.75190.04920.39840.053*
H15B0.56950.09550.38100.053*
C160.6672 (6)0.0005 (3)0.33708 (15)0.0503 (11)
H16A0.60610.05120.35110.060*
H16B0.58650.02080.31320.060*
C170.8514 (6)0.0310 (3)0.31707 (13)0.0423 (10)
C180.9435 (5)0.0536 (3)0.29593 (12)0.0341 (9)
H180.84720.08100.27700.041*
C191.0936 (5)0.0189 (3)0.26382 (12)0.0395 (9)
H191.20800.00730.28090.047*
C201.1404 (6)0.0818 (3)0.22529 (15)0.0500 (12)
C211.0121 (7)0.0725 (3)0.24745 (15)0.0582 (13)
H21A0.97790.06880.21600.070*
H21B1.10440.11950.25090.070*
C220.8384 (7)0.0930 (3)0.27615 (16)0.0549 (12)
H22A0.72490.08110.25940.066*
H22B0.83810.15520.28540.066*
C230.6078 (6)0.5185 (3)0.46879 (16)0.0609 (14)
H23A0.55250.47790.48990.091*
H23B0.54310.51440.44070.091*
H23C0.59870.57850.48010.091*
C240.9094 (6)0.4905 (3)0.50812 (12)0.0520 (11)
H24A1.04280.48910.50450.078*
H24B0.86930.43770.52370.078*
H24C0.87490.54260.52510.078*
C251.1663 (5)0.3518 (3)0.45069 (14)0.0448 (11)
H25A1.26270.31630.43710.067*
H25B1.10630.31770.47390.067*
H25C1.22050.40480.46340.067*
C260.9830 (6)0.1609 (3)0.43158 (12)0.0464 (11)
H26A0.97800.18850.46060.070*
H26B1.11060.15750.42180.070*
H26C0.93140.10170.43330.070*
C270.6862 (5)0.2109 (3)0.32242 (13)0.0416 (10)
H27A0.64940.17300.29800.062*
H27B0.75680.26060.31110.062*
H27C0.57680.23250.33760.062*
C280.9630 (7)0.0780 (3)0.35488 (15)0.0532 (12)
H28A1.00210.03410.37690.064*
H28B0.88330.12130.36980.064*
C291.3386 (8)0.0938 (4)0.21333 (19)0.0841 (19)
H29A1.40840.11030.23990.101*
H29B1.34940.14240.19190.101*
C301.0135 (8)0.1247 (4)0.20139 (15)0.0696 (16)
H30A1.05040.16130.17780.084*
H30B0.88730.11840.20820.084*
C311.2306 (8)0.1665 (4)0.3652 (2)0.0732 (16)
C321.3789 (7)0.2221 (4)0.3428 (2)0.094 (2)
H32A1.49440.21610.35890.141*
H32B1.39570.20190.31260.141*
H32C1.34110.28370.34270.141*
C330.8263 (7)0.7245 (3)0.43739 (18)0.0534 (12)
C340.8185 (9)0.8011 (3)0.46859 (19)0.0819 (18)
H34A0.94130.82610.47190.123*
H34B0.77380.78120.49720.123*
H34C0.73540.84580.45690.123*
O11.1239 (5)0.1224 (2)0.33705 (11)0.0625 (9)
O21.2042 (7)0.1640 (4)0.40533 (18)0.1280 (19)
O30.8996 (4)0.65128 (19)0.45704 (10)0.0473 (7)
O40.7726 (6)0.7259 (2)0.39882 (13)0.0783 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0718 (4)0.1855 (9)0.0816 (4)0.0435 (5)0.0114 (3)0.0252 (5)
C10.039 (2)0.044 (3)0.035 (2)0.0083 (19)0.0101 (17)0.0059 (19)
C20.047 (2)0.037 (3)0.042 (2)0.010 (2)0.0035 (19)0.0031 (19)
C30.050 (2)0.032 (2)0.033 (2)0.0026 (19)0.0026 (18)0.0114 (18)
C40.0410 (19)0.038 (2)0.0307 (19)0.001 (2)0.0084 (16)0.0040 (19)
C50.0329 (19)0.032 (2)0.029 (2)0.0004 (17)0.0074 (16)0.0006 (17)
C60.046 (2)0.042 (3)0.041 (2)0.008 (2)0.0186 (19)0.001 (2)
C70.044 (2)0.033 (2)0.038 (2)0.0085 (19)0.0154 (18)0.0018 (19)
C80.0327 (18)0.031 (2)0.0285 (19)0.0018 (17)0.0032 (16)0.0014 (17)
C90.0260 (17)0.036 (2)0.0257 (18)0.0005 (16)0.0028 (14)0.0018 (16)
C100.0263 (18)0.033 (2)0.0250 (18)0.0032 (16)0.0006 (15)0.0006 (17)
C110.0321 (19)0.038 (2)0.044 (2)0.0041 (19)0.0077 (17)0.0048 (19)
C120.0346 (19)0.034 (2)0.041 (2)0.0028 (17)0.0098 (18)0.0103 (19)
C130.0304 (18)0.031 (2)0.032 (2)0.0034 (16)0.0028 (15)0.0021 (17)
C140.0334 (18)0.031 (2)0.032 (2)0.0026 (18)0.0030 (16)0.0023 (17)
C150.046 (2)0.039 (3)0.048 (3)0.005 (2)0.013 (2)0.006 (2)
C160.056 (2)0.037 (3)0.058 (3)0.016 (2)0.008 (2)0.008 (2)
C170.055 (2)0.031 (2)0.041 (2)0.002 (2)0.0046 (19)0.004 (2)
C180.0378 (18)0.034 (2)0.0303 (18)0.0008 (18)0.0003 (16)0.0001 (17)
C190.050 (2)0.037 (2)0.0312 (19)0.004 (2)0.0009 (16)0.0066 (18)
C200.060 (3)0.049 (3)0.041 (2)0.003 (2)0.010 (2)0.012 (2)
C210.083 (3)0.045 (3)0.047 (3)0.004 (3)0.009 (2)0.012 (2)
C220.069 (3)0.038 (3)0.058 (3)0.007 (2)0.001 (2)0.007 (2)
C230.049 (2)0.052 (3)0.082 (3)0.001 (2)0.024 (2)0.021 (3)
C240.078 (3)0.049 (3)0.029 (2)0.007 (3)0.0065 (19)0.004 (2)
C250.042 (2)0.047 (3)0.045 (2)0.006 (2)0.0109 (19)0.005 (2)
C260.066 (3)0.041 (3)0.033 (2)0.001 (2)0.008 (2)0.007 (2)
C270.0335 (19)0.051 (3)0.041 (2)0.0097 (19)0.0099 (17)0.004 (2)
C280.072 (3)0.036 (3)0.052 (3)0.003 (3)0.003 (2)0.007 (2)
C290.075 (3)0.115 (5)0.062 (3)0.033 (4)0.011 (3)0.009 (4)
C300.089 (4)0.078 (4)0.041 (3)0.016 (3)0.004 (3)0.008 (3)
C310.066 (3)0.074 (4)0.079 (4)0.009 (3)0.014 (3)0.001 (4)
C320.065 (3)0.064 (4)0.153 (6)0.014 (3)0.022 (4)0.005 (4)
C330.056 (3)0.040 (3)0.064 (3)0.004 (2)0.006 (2)0.006 (3)
C340.107 (4)0.046 (3)0.093 (4)0.001 (3)0.018 (4)0.025 (3)
O10.078 (2)0.054 (2)0.055 (2)0.0185 (19)0.0040 (17)0.0052 (17)
O20.109 (3)0.179 (5)0.097 (3)0.039 (3)0.026 (3)0.022 (3)
O30.0630 (18)0.0353 (18)0.0435 (16)0.0022 (15)0.0035 (14)0.0104 (14)
O40.108 (3)0.049 (2)0.078 (3)0.013 (2)0.027 (2)0.005 (2)
Geometric parameters (Å, º) top
Br1—C291.943 (6)C17—C281.550 (6)
C1—C21.537 (5)C17—C181.559 (5)
C1—C101.539 (5)C18—C191.530 (5)
C1—H1A0.9700C18—H180.9800
C1—H1B0.9700C19—C201.522 (6)
C2—C31.504 (6)C19—C211.563 (6)
C2—H2A0.9700C19—H190.9800
C2—H2B0.9700C20—C301.320 (6)
C3—O31.464 (5)C20—C291.473 (7)
C3—C41.542 (6)C21—C221.540 (7)
C3—H30.9800C21—H21A0.9700
C4—C241.534 (5)C21—H21B0.9700
C4—C231.544 (5)C22—H22A0.9700
C4—C51.563 (5)C22—H22B0.9700
C5—C61.546 (5)C23—H23A0.9600
C5—C101.551 (5)C23—H23B0.9600
C5—H50.9800C23—H23C0.9600
C6—C71.531 (6)C24—H24A0.9600
C6—H6A0.9700C24—H24B0.9600
C6—H6B0.9700C24—H24C0.9600
C7—C81.532 (5)C25—H25A0.9600
C7—H7A0.9700C25—H25B0.9600
C7—H7B0.9700C25—H25C0.9600
C8—C261.559 (5)C26—H26A0.9600
C8—C91.574 (5)C26—H26B0.9600
C8—C141.600 (5)C26—H26C0.9600
C9—C111.525 (5)C27—H27A0.9600
C9—C101.588 (5)C27—H27B0.9600
C9—H90.9800C27—H27C0.9600
C10—C251.550 (5)C28—O11.431 (5)
C11—C121.537 (5)C28—H28A0.9700
C11—H11A0.9700C28—H28B0.9700
C11—H11B0.9700C29—H29A0.9700
C12—C131.526 (5)C29—H29B0.9700
C12—H12A0.9700C30—H30A0.9300
C12—H12B0.9700C30—H30B0.9300
C13—C181.540 (5)C31—O21.211 (7)
C13—C141.570 (5)C31—O11.313 (6)
C13—H130.9800C31—C321.504 (8)
C14—C151.558 (5)C32—H32A0.9600
C14—C271.565 (5)C32—H32B0.9600
C15—C161.541 (5)C32—H32C0.9600
C15—H15A0.9700C33—O41.213 (6)
C15—H15B0.9700C33—O31.348 (6)
C16—C171.516 (6)C33—C341.477 (7)
C16—H16A0.9700C34—H34A0.9600
C16—H16B0.9700C34—H34B0.9600
C17—C221.536 (6)C34—H34C0.9600
C2—C1—C10113.4 (3)C16—C17—C28107.3 (4)
C2—C1—H1A108.9C22—C17—C28109.6 (4)
C10—C1—H1A108.9C16—C17—C18106.4 (3)
C2—C1—H1B108.9C22—C17—C18101.1 (3)
C10—C1—H1B108.9C28—C17—C18116.4 (3)
H1A—C1—H1B107.7C19—C18—C13120.5 (3)
C3—C2—C1109.9 (3)C19—C18—C17106.0 (3)
C3—C2—H2A109.7C13—C18—C17111.6 (3)
C1—C2—H2A109.7C19—C18—H18105.9
C3—C2—H2B109.7C13—C18—H18105.9
C1—C2—H2B109.7C17—C18—H18105.9
H2A—C2—H2B108.2C20—C19—C18114.7 (3)
O3—C3—C2109.8 (3)C20—C19—C21112.7 (3)
O3—C3—C4107.9 (3)C18—C19—C21103.3 (3)
C2—C3—C4113.6 (3)C20—C19—H19108.6
O3—C3—H3108.5C18—C19—H19108.6
C2—C3—H3108.5C21—C19—H19108.6
C4—C3—H3108.5C30—C20—C29118.1 (5)
C24—C4—C3112.0 (3)C30—C20—C19123.9 (4)
C24—C4—C23108.1 (3)C29—C20—C19118.0 (5)
C3—C4—C23106.9 (3)C22—C21—C19107.5 (4)
C24—C4—C5115.1 (3)C22—C21—H21A110.2
C3—C4—C5105.8 (3)C19—C21—H21A110.2
C23—C4—C5108.8 (3)C22—C21—H21B110.2
C6—C5—C10110.1 (3)C19—C21—H21B110.2
C6—C5—C4114.3 (3)H21A—C21—H21B108.5
C10—C5—C4117.7 (3)C17—C22—C21105.9 (4)
C6—C5—H5104.4C17—C22—H22A110.6
C10—C5—H5104.4C21—C22—H22A110.6
C4—C5—H5104.4C17—C22—H22B110.6
C7—C6—C5110.5 (3)C21—C22—H22B110.6
C7—C6—H6A109.6H22A—C22—H22B108.7
C5—C6—H6A109.6C4—C23—H23A109.5
C7—C6—H6B109.6C4—C23—H23B109.5
C5—C6—H6B109.6H23A—C23—H23B109.5
H6A—C6—H6B108.1C4—C23—H23C109.5
C6—C7—C8113.7 (3)H23A—C23—H23C109.5
C6—C7—H7A108.8H23B—C23—H23C109.5
C8—C7—H7A108.8C4—C24—H24A109.5
C6—C7—H7B108.8C4—C24—H24B109.5
C8—C7—H7B108.8H24A—C24—H24B109.5
H7A—C7—H7B107.7C4—C24—H24C109.5
C7—C8—C26106.8 (3)H24A—C24—H24C109.5
C7—C8—C9109.5 (3)H24B—C24—H24C109.5
C26—C8—C9111.9 (3)C10—C25—H25A109.5
C7—C8—C14110.5 (3)C10—C25—H25B109.5
C26—C8—C14109.2 (3)H25A—C25—H25B109.5
C9—C8—C14109.0 (3)C10—C25—H25C109.5
C11—C9—C8110.4 (3)H25A—C25—H25C109.5
C11—C9—C10114.8 (3)H25B—C25—H25C109.5
C8—C9—C10116.5 (3)C8—C26—H26A109.5
C11—C9—H9104.5C8—C26—H26B109.5
C8—C9—H9104.5H26A—C26—H26B109.5
C10—C9—H9104.5C8—C26—H26C109.5
C1—C10—C25107.8 (3)H26A—C26—H26C109.5
C1—C10—C5107.7 (3)H26B—C26—H26C109.5
C25—C10—C5114.1 (3)C14—C27—H27A109.5
C1—C10—C9108.3 (3)C14—C27—H27B109.5
C25—C10—C9112.4 (3)H27A—C27—H27B109.5
C5—C10—C9106.4 (3)C14—C27—H27C109.5
C9—C11—C12113.4 (3)H27A—C27—H27C109.5
C9—C11—H11A108.9H27B—C27—H27C109.5
C12—C11—H11A108.9O1—C28—C17110.7 (3)
C9—C11—H11B108.9O1—C28—H28A109.5
C12—C11—H11B108.9C17—C28—H28A109.5
H11A—C11—H11B107.7O1—C28—H28B109.5
C13—C12—C11112.4 (3)C17—C28—H28B109.5
C13—C12—H12A109.1H28A—C28—H28B108.1
C11—C12—H12A109.1C20—C29—Br1112.4 (4)
C13—C12—H12B109.1C20—C29—H29A109.1
C11—C12—H12B109.1Br1—C29—H29A109.1
H12A—C12—H12B107.9C20—C29—H29B109.1
C12—C13—C18116.0 (3)Br1—C29—H29B109.1
C12—C13—C14110.6 (3)H29A—C29—H29B107.9
C18—C13—C14109.9 (3)C20—C30—H30A120.0
C12—C13—H13106.6C20—C30—H30B120.0
C18—C13—H13106.6H30A—C30—H30B120.0
C14—C13—H13106.6O2—C31—O1121.8 (6)
C15—C14—C27107.6 (3)O2—C31—C32124.4 (6)
C15—C14—C13110.5 (3)O1—C31—C32113.7 (6)
C27—C14—C13109.6 (3)C31—C32—H32A109.5
C15—C14—C8110.6 (3)C31—C32—H32B109.5
C27—C14—C8110.1 (3)H32A—C32—H32B109.5
C13—C14—C8108.5 (3)C31—C32—H32C109.5
C16—C15—C14115.1 (3)H32A—C32—H32C109.5
C16—C15—H15A108.5H32B—C32—H32C109.5
C14—C15—H15A108.5O4—C33—O3123.4 (4)
C16—C15—H15B108.5O4—C33—C34124.9 (5)
C14—C15—H15B108.5O3—C33—C34111.7 (5)
H15A—C15—H15B107.5C33—C34—H34A109.5
C17—C16—C15112.6 (3)C33—C34—H34B109.5
C17—C16—H16A109.1H34A—C34—H34B109.5
C15—C16—H16A109.1C33—C34—H34C109.5
C17—C16—H16B109.1H34A—C34—H34C109.5
C15—C16—H16B109.1H34B—C34—H34C109.5
H16A—C16—H16B107.8C31—O1—C28117.5 (4)
C16—C17—C22116.2 (3)C33—O3—C3118.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C32—H32A···O4i0.962.483.365 (7)154
C28—H28B···O4ii0.972.573.487 (6)158
Symmetry codes: (i) x+1, y1, z; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC34H53BrO4
Mr605.67
Crystal system, space groupOrthorhombic, P212121
Temperature (K)291
a, b, c (Å)7.152 (3), 14.946 (7), 29.837 (12)
V3)3189 (2)
Z4
Radiation typeMo Kα
µ (mm1)1.32
Crystal size (mm)0.40 × 0.38 × 0.37
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.622, 0.642
No. of measured, independent and
observed [I > 2σ(I)] reflections
23319, 5578, 3534
Rint0.102
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.145, 0.94
No. of reflections5578
No. of parameters358
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.45, 0.58
Absolute structureFlack (1983), 2346 Friedel pairs
Absolute structure parameter0.024 (12)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C32—H32A···O4i0.962.483.365 (7)154.2
C28—H28B···O4ii0.972.573.487 (6)158.3
Symmetry codes: (i) x+1, y1, z; (ii) x, y1, z.
 

Acknowledgements

The authors thank the `948' Project of State Forestry Administration (2006–4-119) and the Innovation Fund for Outstanding Young Teachers of Northeast Forestry University for supporting of this study.

References

First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationKim, D. S., Pezzuto, J. M. & Pisha, E. (1998). Bioorg. Med. Chem. Lett. 8, 1707–1712.  Web of Science CrossRef CAS PubMed Google Scholar
First citationMohamed, I. E., Choudhary, M. I., Ali, S., Anjum, S. & Atta-ur-Rahman (2006). Acta Cryst. E62, o1352–o1354.  Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSun, C.-I., Wang, H.-K., Kashiwada, Y., Shen, J.-K., Cosentino, L.-M., Chen, C.-H., Yang, L.-M. & Lee, K.-H. (1998). J. Med. Chem. 41, 4648–4657.  Web of Science CrossRef CAS PubMed Google Scholar

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