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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

16α-Bromo-17β-hydr­­oxy-5α-androstan-3β-yl acetate

aKey Laboratory of Forest Resources Conservation and Use in the Southwest Mountains of China (Ministry of Education), Southwest Forestry University, Kunming 650224, People's Republic of China, and bSchool of Chemical Science and Technology, Key Laboratory of Medicinal Chemistry for Natural Resources, (Ministry of Education), Yunnan University, Kunming 650091, People's Republic of China
*Correspondence e-mail: spuwk@yahoo.com.cn

(Received 28 January 2010; accepted 27 February 2010; online 6 March 2010)

The title compound, C21H33BrO3, an inter­mediate in the synthesis of the neuromuscular blocking agent rocuronium bromide, contains two independent mol­ecules in the asymmetric unit, which have almost identical geometries: in both mol­ecules, the steroidal rings A, B and C have slightly flattened chair conformations and ring D assumes a half-chair conformation. In the crystal, O—H⋯O hydrogen bonds and weak C—H⋯O and C—H⋯Br inter­actions help to establish the packing.

Related literature

For further information on rocuronium bromide, see: Tuba et al. (2002[Tuba, Z., Maho, S. & Vizi, S. (2002). Curr. Med. Chem. 9, 1507-1536.]); Auer (2007[Auer, U. (2007). Vet. J. 173, 422-427.]). For the synthesis, see: Fajkos & Sanda (1962[Fajkos, J. & Sanda, V. (1962). Collect. Czech. Chem. Commun. 27, 355-358.]).

[Scheme 1]

Experimental

Crystal data
  • C21H33BrO3

  • Mr = 413.38

  • Monoclinic, P 21

  • a = 11.1010 (12) Å

  • b = 7.6637 (8) Å

  • c = 24.383 (3) Å

  • β = 93.036 (2)°

  • V = 2071.5 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.00 mm−1

  • T = 298 K

  • 0.26 × 0.18 × 0.12 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.624, Tmax = 0.795

  • 13607 measured reflections

  • 9114 independent reflections

  • 3737 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.125

  • S = 0.87

  • 9114 reflections

  • 459 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.29 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3537 Friedel pairs

  • Flack parameter: 0.016 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3A⋯O6i 0.82 2.12 2.936 (6) 179
O6—H6⋯O5ii 0.82 1.97 2.757 (6) 160
C16—H16⋯O6i 0.98 2.56 3.347 (7) 137
C23—H22A⋯Br1iii 0.97 2.92 3.868 (6) 166
C37—H37⋯Br1iv 0.98 2.87 3.788 (6) 156
Symmetry codes: (i) x, y, z-1; (ii) [-x+2, y+{\script{1\over 2}}, -z+2]; (iii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iv) x, y, z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL.

Supporting information


Comment top

As part of our ongoing investigation of the synthese of rocuronium bromide which is a new neuromuscular blocking agent (Tuba et al., 2002; Auer, 2007), the title compound was obtained as an intermediate.

The title compound, C21H33BrO3, crystallizes in a monoclinic unit cell. The molecular structure is shown in Fig. 1., which contains two crystallographically independent molecules in the asymmetric unit which have almost identical geometry. Rings A, B and C have chair conformations which are slightly flattened and D ring assumes a half-chair conformation in both molecules.

Cohesion of the crystals can be attributed to van der Waals and weak molecular O—H···O interactions (Table 1).

Related literature top

For further information on rocuronium bromide, see: Tuba et al. (2002); Auer (2007). For the synthesis, see: Fajkos & Sanda (1962).

Experimental top

The title compound was synthesized according to the procedure of Fajkos et al. (1962). Colourless prisms of (I) were obtained from a mixture of ethyl acetate and petroleum ether by slow evaporation at room temperature.

Refinement top

Methyl H atoms were placed in calculated positions with C—H = 0.96Å and the torsion angle was refined to fit the electron density; Uiso(H) = 1.5Ueq(C). Other H atoms were placed in calculated positions with C—H = 0.97–0.98 Å and O—H = 0.82 Å, and refined in riding mode; Uiso(H) = 1.2Ueq(C, O).

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. The molecular structure of (I) showing 30% probability displacement ellipsoids.
16α-Bromo-17β-hydroxy-5α-androstan-3β-yl acetate top
Crystal data top
C21H33BrO3F(000) = 872
Mr = 413.38Dx = 1.326 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9114 reflections
a = 11.1010 (12) Åθ = 2.2–28.4°
b = 7.6637 (8) ŵ = 2.00 mm1
c = 24.383 (3) ÅT = 298 K
β = 93.036 (2)°Prism, colourless
V = 2071.5 (4) Å30.26 × 0.18 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
9114 independent reflections
Radiation source: fine-focus sealed tube3737 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scansθmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1414
Tmin = 0.624, Tmax = 0.795k = 109
13607 measured reflectionsl = 3221
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053 w = 1/[σ2(Fo2)]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.125(Δ/σ)max = 0.001
S = 0.87Δρmax = 0.20 e Å3
9114 reflectionsΔρmin = 0.29 e Å3
459 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0010 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 3537 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.016 (9)
Crystal data top
C21H33BrO3V = 2071.5 (4) Å3
Mr = 413.38Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.1010 (12) ŵ = 2.00 mm1
b = 7.6637 (8) ÅT = 298 K
c = 24.383 (3) Å0.26 × 0.18 × 0.12 mm
β = 93.036 (2)°
Data collection top
Bruker SMART CCD
diffractometer
9114 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
3737 reflections with I > 2σ(I)
Tmin = 0.624, Tmax = 0.795Rint = 0.042
13607 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.125Δρmax = 0.20 e Å3
S = 0.87Δρmin = 0.29 e Å3
9114 reflectionsAbsolute structure: Flack (1983), 3537 Friedel pairs
459 parametersAbsolute structure parameter: 0.016 (9)
1 restraint
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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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
Br10.33539 (6)0.31032 (9)0.21950 (3)0.0820 (2)
Br20.69555 (9)0.09933 (13)1.21764 (4)0.1268 (4)
C10.1761 (6)0.9883 (7)0.4929 (2)0.0587 (17)
H1A0.10250.96620.47080.070*
H1B0.21291.09270.47880.070*
C20.1441 (6)1.0208 (8)0.5527 (2)0.0650 (17)
H2A0.21621.05420.57440.078*
H2B0.08681.11610.55390.078*
C30.0910 (5)0.8609 (7)0.5769 (2)0.0515 (15)
H30.01350.83630.55730.062*
C40.1719 (5)0.7031 (7)0.5725 (2)0.0540 (15)
H4A0.13110.60090.58590.065*
H4B0.24520.72040.59530.065*
C50.2041 (5)0.6725 (7)0.5133 (2)0.0476 (14)
H50.12710.65490.49250.057*
C60.2747 (5)0.5055 (7)0.5065 (2)0.0573 (16)
H6A0.23220.40930.52270.069*
H6B0.35310.51620.52570.069*
C70.2912 (5)0.4670 (7)0.4461 (2)0.0537 (15)
H7A0.34370.36650.44340.064*
H7B0.21360.43720.42850.064*
C80.3445 (4)0.6188 (6)0.41582 (19)0.0386 (12)
H80.42820.63400.42990.046*
C90.2764 (4)0.7906 (7)0.42545 (18)0.0409 (12)
H90.19430.77220.40980.049*
C100.2628 (4)0.8334 (7)0.48690 (19)0.0414 (12)
C110.3289 (5)0.9417 (7)0.3922 (2)0.0535 (15)
H11A0.27961.04480.39640.064*
H11B0.40960.96800.40720.064*
C120.3347 (5)0.8993 (7)0.3304 (2)0.0591 (16)
H12A0.25330.88940.31410.071*
H12B0.37440.99430.31230.071*
C130.4018 (4)0.7322 (7)0.3212 (2)0.0449 (14)
C140.3454 (4)0.5866 (7)0.35444 (19)0.0452 (13)
H140.26020.58430.34170.054*
C150.3986 (5)0.4182 (7)0.3326 (2)0.0562 (15)
H15A0.34210.32230.33470.067*
H15B0.47300.38770.35310.067*
C160.4224 (5)0.4631 (7)0.2720 (2)0.0572 (16)
H160.50910.45350.26670.069*
C170.3837 (5)0.6541 (7)0.2639 (2)0.0550 (15)
H170.29670.65370.25460.066*
C180.3861 (4)0.8748 (8)0.5150 (2)0.0655 (18)
H18A0.37700.89560.55340.098*
H18B0.41900.97690.49860.098*
H18C0.43950.77790.51070.098*
C190.5391 (5)0.7546 (8)0.3358 (2)0.0682 (18)
H19A0.57940.64530.33100.102*
H19B0.55100.79180.37330.102*
H19C0.57160.84060.31200.102*
C200.0136 (6)0.8036 (11)0.6582 (3)0.0664 (16)
C220.9194 (5)0.5784 (8)0.9099 (2)0.0636 (16)
H21A0.89610.69530.92030.076*
H21B0.99360.54980.93070.076*
C230.9434 (5)0.5775 (9)0.8484 (2)0.0681 (17)
H22A0.87200.61700.82730.082*
H22B1.00900.65680.84150.082*
C240.9754 (5)0.3973 (9)0.8309 (2)0.0665 (18)
H231.05310.36380.84880.080*
C250.8804 (5)0.2637 (8)0.8443 (2)0.0741 (19)
H24A0.90750.14810.83440.089*
H24B0.80610.28840.82310.089*
C260.8571 (5)0.2682 (7)0.9057 (2)0.0562 (16)
H250.93420.24050.92520.067*
C270.7673 (5)0.1253 (8)0.9218 (3)0.0680 (17)
H26A0.68830.14900.90450.082*
H26B0.79400.01260.90910.082*
C280.7594 (5)0.1218 (8)0.9839 (2)0.0645 (17)
H27A0.83660.08501.00060.077*
H27B0.69950.03650.99340.077*
C290.7262 (4)0.2992 (7)1.0077 (2)0.0488 (13)
H280.64470.32990.99340.059*
C300.8140 (5)0.4417 (7)0.9899 (2)0.0491 (15)
H290.89430.40471.00400.059*
C310.8203 (5)0.4497 (7)0.9258 (2)0.0486 (15)
C320.7916 (5)0.6187 (7)1.0166 (2)0.0653 (16)
H31A0.71530.66521.00190.078*
H31B0.85470.69921.00720.078*
C330.7886 (5)0.6073 (8)1.0793 (2)0.0627 (16)
H32A0.86790.57511.09460.075*
H32B0.76830.72071.09390.075*
C340.6968 (5)0.4737 (7)1.0961 (3)0.0523 (16)
C350.7276 (4)0.2988 (8)1.0701 (2)0.0525 (14)
H340.81150.27541.08230.063*
C360.6519 (6)0.1651 (8)1.1007 (3)0.075 (2)
H35A0.57390.14701.08170.090*
H35B0.69350.05401.10430.090*
C370.6380 (5)0.2497 (8)1.1572 (3)0.072 (2)
H370.55230.27391.16130.087*
C380.7055 (5)0.4229 (8)1.1569 (3)0.0611 (17)
H38D0.79030.40241.16830.073*
C390.6978 (5)0.5097 (9)0.8988 (2)0.073 (2)
H38A0.69960.49900.85960.109*
H38B0.68350.62930.90820.109*
H38C0.63430.43810.91170.109*
C411.0671 (6)0.3018 (11)0.7497 (3)0.0749 (18)
C421.0744 (6)0.3298 (10)0.6886 (2)0.100 (2)
H41A1.13870.26040.67540.150*
H41B1.08980.45080.68160.150*
H41C0.99950.29610.67020.150*
C210.0195 (6)0.8451 (10)0.7174 (2)0.092 (2)
H42A0.06790.94760.72160.138*
H42B0.06050.86580.73300.138*
H42C0.05480.74890.73600.138*
O10.0693 (3)0.8992 (5)0.63361 (16)0.0658 (11)
O20.0737 (4)0.6942 (7)0.63403 (18)0.0890 (15)
O30.4395 (4)0.7394 (5)0.22015 (17)0.0806 (13)
H3A0.50050.68590.21280.121*
O40.9865 (3)0.4031 (6)0.77130 (16)0.0752 (13)
O51.1284 (4)0.2026 (7)0.77638 (19)0.0934 (15)
O60.6557 (4)0.5418 (6)1.19406 (19)0.0867 (15)
H60.70920.60551.20720.130*
C400.5684 (5)0.5365 (9)1.0800 (3)0.083 (2)
H43A0.55210.64171.09970.124*
H43B0.51150.44821.08910.124*
H43C0.56130.55901.04130.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0874 (5)0.0966 (5)0.0636 (4)0.0233 (5)0.0199 (3)0.0292 (4)
Br20.1275 (7)0.1339 (8)0.1199 (8)0.0042 (6)0.0157 (6)0.0642 (6)
C10.077 (4)0.046 (4)0.055 (4)0.001 (3)0.016 (3)0.001 (3)
C20.079 (4)0.059 (4)0.059 (4)0.011 (3)0.021 (3)0.007 (3)
C30.059 (4)0.060 (4)0.036 (3)0.003 (3)0.012 (3)0.005 (3)
C40.057 (4)0.058 (4)0.047 (4)0.004 (3)0.010 (3)0.002 (3)
C50.055 (3)0.046 (4)0.043 (4)0.002 (3)0.008 (3)0.001 (3)
C60.078 (4)0.047 (4)0.048 (4)0.002 (3)0.012 (3)0.008 (3)
C70.073 (4)0.047 (4)0.042 (4)0.003 (3)0.015 (3)0.006 (3)
C80.044 (3)0.036 (3)0.036 (3)0.001 (3)0.002 (2)0.007 (2)
C90.046 (3)0.040 (3)0.037 (3)0.004 (3)0.001 (2)0.000 (3)
C100.043 (3)0.042 (3)0.040 (3)0.001 (3)0.009 (2)0.003 (3)
C110.074 (4)0.042 (4)0.047 (4)0.008 (3)0.022 (3)0.003 (3)
C120.082 (4)0.049 (4)0.048 (4)0.005 (3)0.019 (3)0.007 (3)
C130.043 (3)0.049 (3)0.044 (4)0.000 (3)0.008 (3)0.001 (3)
C140.053 (3)0.051 (3)0.031 (3)0.003 (3)0.004 (3)0.001 (3)
C150.084 (4)0.045 (3)0.041 (4)0.002 (3)0.013 (3)0.007 (3)
C160.063 (4)0.056 (4)0.053 (4)0.004 (3)0.008 (3)0.008 (3)
C170.058 (4)0.071 (5)0.036 (3)0.007 (3)0.007 (3)0.000 (3)
C180.060 (4)0.090 (5)0.046 (4)0.023 (3)0.006 (3)0.012 (3)
C190.068 (4)0.080 (5)0.058 (4)0.023 (3)0.017 (3)0.001 (3)
C200.070 (4)0.076 (5)0.055 (4)0.001 (5)0.018 (4)0.012 (4)
C220.079 (4)0.066 (4)0.047 (4)0.010 (4)0.008 (3)0.002 (3)
C230.076 (4)0.070 (5)0.058 (4)0.009 (4)0.009 (3)0.005 (4)
C240.061 (4)0.093 (5)0.046 (4)0.006 (4)0.002 (3)0.006 (4)
C250.080 (4)0.080 (5)0.061 (4)0.006 (4)0.009 (4)0.007 (3)
C260.054 (3)0.064 (5)0.049 (4)0.000 (3)0.006 (3)0.005 (3)
C270.079 (4)0.049 (4)0.076 (5)0.010 (4)0.002 (4)0.011 (3)
C280.068 (4)0.056 (4)0.070 (5)0.012 (3)0.009 (3)0.005 (3)
C290.039 (3)0.042 (3)0.065 (4)0.001 (3)0.002 (2)0.005 (3)
C300.043 (3)0.045 (4)0.059 (4)0.000 (3)0.000 (3)0.004 (3)
C310.044 (3)0.049 (4)0.052 (4)0.005 (3)0.007 (3)0.001 (3)
C320.088 (4)0.046 (4)0.063 (4)0.012 (3)0.016 (3)0.001 (3)
C330.082 (4)0.054 (4)0.054 (4)0.010 (4)0.015 (3)0.006 (3)
C340.040 (3)0.053 (4)0.065 (4)0.004 (3)0.010 (3)0.002 (3)
C350.042 (3)0.052 (4)0.064 (4)0.007 (3)0.009 (3)0.004 (4)
C360.073 (4)0.062 (4)0.092 (6)0.015 (4)0.017 (4)0.011 (4)
C370.053 (4)0.089 (6)0.077 (5)0.007 (4)0.015 (3)0.017 (4)
C380.042 (3)0.070 (4)0.072 (5)0.004 (3)0.014 (3)0.007 (4)
C390.064 (4)0.095 (5)0.058 (4)0.017 (4)0.009 (3)0.006 (4)
C410.091 (5)0.069 (5)0.065 (5)0.024 (5)0.014 (4)0.006 (4)
C420.144 (6)0.097 (6)0.061 (4)0.005 (5)0.034 (4)0.018 (4)
C210.109 (5)0.109 (6)0.061 (5)0.002 (5)0.036 (4)0.004 (4)
O10.081 (3)0.073 (3)0.046 (3)0.011 (2)0.025 (2)0.007 (2)
O20.081 (3)0.118 (4)0.068 (3)0.027 (3)0.014 (3)0.001 (3)
O30.110 (4)0.080 (3)0.056 (3)0.007 (2)0.040 (3)0.012 (2)
O40.077 (3)0.097 (3)0.051 (3)0.024 (3)0.000 (2)0.005 (2)
O50.097 (4)0.096 (4)0.088 (4)0.031 (3)0.009 (3)0.002 (3)
O60.078 (3)0.106 (4)0.079 (3)0.012 (3)0.032 (3)0.021 (3)
C400.064 (4)0.091 (5)0.094 (5)0.020 (4)0.007 (4)0.002 (4)
Geometric parameters (Å, º) top
Br1—C161.952 (5)C22—H21B0.9700
Br2—C371.951 (6)C23—C241.494 (8)
C1—C101.540 (7)C23—H22A0.9700
C1—C21.540 (7)C23—H22B0.9700
C1—H1A0.9700C24—O41.466 (6)
C1—H1B0.9700C24—C251.518 (8)
C2—C31.495 (7)C24—H230.9800
C2—H2A0.9700C25—C261.533 (7)
C2—H2B0.9700C25—H24A0.9700
C3—O11.446 (6)C25—H24B0.9700
C3—C41.514 (7)C26—C311.537 (7)
C3—H30.9800C26—C271.546 (7)
C4—C51.523 (7)C26—H250.9800
C4—H4A0.9700C27—C281.523 (7)
C4—H4B0.9700C27—H26A0.9700
C5—C61.514 (7)C27—H26B0.9700
C5—C101.551 (7)C28—C291.530 (8)
C5—H50.9800C28—H27A0.9700
C6—C71.522 (7)C28—H27B0.9700
C6—H6A0.9700C29—C351.521 (6)
C6—H6B0.9700C29—C301.542 (7)
C7—C81.515 (7)C29—H280.9800
C7—H7A0.9700C30—C321.531 (8)
C7—H7B0.9700C30—C311.569 (7)
C8—C141.517 (6)C30—H290.9800
C8—C91.542 (6)C31—C391.549 (7)
C8—H80.9800C32—C331.532 (7)
C9—C111.545 (7)C32—H31A0.9700
C9—C101.549 (6)C32—H31B0.9700
C9—H90.9800C33—C341.517 (7)
C10—C181.531 (6)C33—H32A0.9700
C11—C121.546 (7)C33—H32B0.9700
C11—H11A0.9700C34—C351.528 (7)
C11—H11B0.9700C34—C381.532 (8)
C12—C131.504 (7)C34—C401.536 (7)
C12—H12A0.9700C35—C361.542 (7)
C12—H12B0.9700C35—H340.9800
C13—C171.525 (7)C36—C371.538 (8)
C13—C141.532 (7)C36—H35A0.9700
C13—C191.556 (7)C36—H35B0.9700
C14—C151.526 (7)C37—C381.524 (8)
C14—H140.9800C37—H370.9800
C15—C161.555 (7)C38—O61.417 (7)
C15—H15A0.9700C38—H38D0.9800
C15—H15B0.9700C39—H38A0.9600
C16—C171.536 (7)C39—H38B0.9600
C16—H160.9800C39—H38C0.9600
C17—O31.420 (6)C41—O51.191 (7)
C17—H170.9800C41—O41.316 (7)
C18—H18A0.9600C41—C421.509 (8)
C18—H18B0.9600C42—H41A0.9600
C18—H18C0.9600C42—H41B0.9600
C19—H19A0.9600C42—H41C0.9600
C19—H19B0.9600C21—H42A0.9600
C19—H19C0.9600C21—H42B0.9600
C20—O21.207 (7)C21—H42C0.9600
C20—O11.343 (7)O3—H3A0.8200
C20—C211.482 (8)O6—H60.8200
C22—C231.537 (7)C40—H43A0.9600
C22—C311.541 (7)C40—H43B0.9600
C22—H21A0.9700C40—H43C0.9600
C10—C1—C2113.1 (4)C22—C23—H22A109.7
C10—C1—H1A109.0C24—C23—H22B109.7
C2—C1—H1A109.0C22—C23—H22B109.7
C10—C1—H1B109.0H22A—C23—H22B108.2
C2—C1—H1B109.0O4—C24—C23106.8 (5)
H1A—C1—H1B107.8O4—C24—C25109.2 (5)
C3—C2—C1110.9 (5)C23—C24—C25112.5 (5)
C3—C2—H2A109.5O4—C24—H23109.4
C1—C2—H2A109.5C23—C24—H23109.4
C3—C2—H2B109.5C25—C24—H23109.4
C1—C2—H2B109.5C24—C25—C26110.5 (5)
H2A—C2—H2B108.1C24—C25—H24A109.5
O1—C3—C2107.5 (4)C26—C25—H24A109.5
O1—C3—C4111.1 (4)C24—C25—H24B109.5
C2—C3—C4112.3 (4)C26—C25—H24B109.5
O1—C3—H3108.6H24A—C25—H24B108.1
C2—C3—H3108.6C25—C26—C31113.1 (5)
C4—C3—H3108.6C25—C26—C27112.1 (5)
C3—C4—C5111.2 (5)C31—C26—C27112.0 (5)
C3—C4—H4A109.4C25—C26—H25106.3
C5—C4—H4A109.4C31—C26—H25106.3
C3—C4—H4B109.4C27—C26—H25106.3
C5—C4—H4B109.4C28—C27—C26109.7 (5)
H4A—C4—H4B108.0C28—C27—H26A109.7
C6—C5—C4112.5 (4)C26—C27—H26A109.7
C6—C5—C10113.3 (4)C28—C27—H26B109.7
C4—C5—C10113.3 (4)C26—C27—H26B109.7
C6—C5—H5105.6H26A—C27—H26B108.2
C4—C5—H5105.6C27—C28—C29112.9 (5)
C10—C5—H5105.6C27—C28—H27A109.0
C5—C6—C7111.1 (4)C29—C28—H27A109.0
C5—C6—H6A109.4C27—C28—H27B109.0
C7—C6—H6A109.4C29—C28—H27B109.0
C5—C6—H6B109.4H27A—C28—H27B107.8
C7—C6—H6B109.4C35—C29—C28112.7 (5)
H6A—C6—H6B108.0C35—C29—C30108.1 (4)
C8—C7—C6113.1 (4)C28—C29—C30110.7 (4)
C8—C7—H7A109.0C35—C29—H28108.4
C6—C7—H7A109.0C28—C29—H28108.4
C8—C7—H7B109.0C30—C29—H28108.4
C6—C7—H7B109.0C32—C30—C29112.8 (5)
H7A—C7—H7B107.8C32—C30—C31114.0 (5)
C7—C8—C14112.3 (4)C29—C30—C31111.7 (4)
C7—C8—C9112.0 (4)C32—C30—H29105.8
C14—C8—C9108.5 (4)C29—C30—H29105.8
C7—C8—H8108.0C31—C30—H29105.8
C14—C8—H8108.0C26—C31—C22107.1 (4)
C9—C8—H8108.0C26—C31—C39112.1 (5)
C8—C9—C11111.0 (4)C22—C31—C39109.0 (5)
C8—C9—C10113.7 (4)C26—C31—C30108.0 (4)
C11—C9—C10114.0 (4)C22—C31—C30110.2 (4)
C8—C9—H9105.8C39—C31—C30110.5 (5)
C11—C9—H9105.8C30—C32—C33112.7 (5)
C10—C9—H9105.8C30—C32—H31A109.0
C18—C10—C1110.2 (5)C33—C32—H31A109.0
C18—C10—C9110.3 (4)C30—C32—H31B109.0
C1—C10—C9110.4 (4)C33—C32—H31B109.0
C18—C10—C5111.4 (4)H31A—C32—H31B107.8
C1—C10—C5107.1 (4)C34—C33—C32111.0 (5)
C9—C10—C5107.3 (4)C34—C33—H32A109.4
C12—C11—C9113.0 (4)C32—C33—H32A109.4
C12—C11—H11A109.0C34—C33—H32B109.4
C9—C11—H11A109.0C32—C33—H32B109.4
C12—C11—H11B109.0H32A—C33—H32B108.0
C9—C11—H11B109.0C33—C34—C35108.2 (4)
H11A—C11—H11B107.8C33—C34—C38115.1 (5)
C13—C12—C11111.7 (5)C35—C34—C38100.1 (5)
C13—C12—H12A109.3C33—C34—C40110.3 (5)
C11—C12—H12A109.3C35—C34—C40113.2 (5)
C13—C12—H12B109.3C38—C34—C40109.6 (5)
C11—C12—H12B109.3C29—C35—C34115.0 (5)
H12A—C12—H12B107.9C29—C35—C36120.6 (5)
C12—C13—C17115.4 (5)C34—C35—C36104.1 (4)
C12—C13—C14108.8 (4)C29—C35—H34105.3
C17—C13—C1499.3 (4)C34—C35—H34105.3
C12—C13—C19111.0 (5)C36—C35—H34105.3
C17—C13—C19109.4 (4)C37—C36—C35103.7 (5)
C14—C13—C19112.5 (4)C37—C36—H35A111.0
C8—C14—C15120.3 (4)C35—C36—H35A111.0
C8—C14—C13115.3 (4)C37—C36—H35B111.0
C15—C14—C13104.8 (4)C35—C36—H35B111.0
C8—C14—H14105.0H35A—C36—H35B109.0
C15—C14—H14105.0C38—C37—C36106.9 (5)
C13—C14—H14105.0C38—C37—Br2112.1 (4)
C14—C15—C16103.5 (4)C36—C37—Br2112.5 (4)
C14—C15—H15A111.1C38—C37—H37108.4
C16—C15—H15A111.1C36—C37—H37108.4
C14—C15—H15B111.1Br2—C37—H37108.4
C16—C15—H15B111.1O6—C38—C37110.4 (5)
H15A—C15—H15B109.0O6—C38—C34116.7 (5)
C17—C16—C15105.8 (4)C37—C38—C34102.7 (5)
C17—C16—Br1111.2 (4)O6—C38—H38D108.9
C15—C16—Br1112.8 (4)C37—C38—H38D108.9
C17—C16—H16109.0C34—C38—H38D108.9
C15—C16—H16109.0C31—C39—H38A109.5
Br1—C16—H16109.0C31—C39—H38B109.5
O3—C17—C13117.8 (5)H38A—C39—H38B109.5
O3—C17—C16113.9 (4)C31—C39—H38C109.5
C13—C17—C16103.5 (4)H38A—C39—H38C109.5
O3—C17—H17107.0H38B—C39—H38C109.5
C13—C17—H17107.0O5—C41—O4122.6 (6)
C16—C17—H17107.0O5—C41—C42124.8 (6)
C10—C18—H18A109.5O4—C41—C42112.6 (7)
C10—C18—H18B109.5C41—C42—H41A109.5
H18A—C18—H18B109.5C41—C42—H41B109.5
C10—C18—H18C109.5H41A—C42—H41B109.5
H18A—C18—H18C109.5C41—C42—H41C109.5
H18B—C18—H18C109.5H41A—C42—H41C109.5
C13—C19—H19A109.5H41B—C42—H41C109.5
C13—C19—H19B109.5C20—C21—H42A109.5
H19A—C19—H19B109.5C20—C21—H42B109.5
C13—C19—H19C109.5H42A—C21—H42B109.5
H19A—C19—H19C109.5C20—C21—H42C109.5
H19B—C19—H19C109.5H42A—C21—H42C109.5
O2—C20—O1122.3 (6)H42B—C21—H42C109.5
O2—C20—C21125.0 (6)C20—O1—C3118.0 (5)
O1—C20—C21112.6 (7)C17—O3—H3A109.5
C23—C22—C31113.9 (5)C41—O4—C24118.3 (5)
C23—C22—H21A108.8C38—O6—H6109.5
C31—C22—H21A108.8C34—C40—H43A109.5
C23—C22—H21B108.8C34—C40—H43B109.5
C31—C22—H21B108.8H43A—C40—H43B109.5
H21A—C22—H21B107.7C34—C40—H43C109.5
C24—C23—C22109.8 (5)H43A—C40—H43C109.5
C24—C23—H22A109.7H43B—C40—H43C109.5
C10—C1—C2—C356.7 (7)C23—C24—C25—C2655.6 (7)
C1—C2—C3—O1177.1 (4)C24—C25—C26—C3156.1 (6)
C1—C2—C3—C454.6 (7)C24—C25—C26—C27176.0 (5)
O1—C3—C4—C5174.8 (4)C25—C26—C27—C28173.2 (5)
C2—C3—C4—C554.5 (6)C31—C26—C27—C2858.4 (6)
C3—C4—C5—C6174.3 (4)C26—C27—C28—C2955.4 (6)
C3—C4—C5—C1055.6 (6)C27—C28—C29—C35175.7 (4)
C4—C5—C6—C7172.7 (5)C27—C28—C29—C3054.5 (6)
C10—C5—C6—C757.2 (6)C35—C29—C30—C3251.0 (6)
C5—C6—C7—C852.8 (6)C28—C29—C30—C32174.9 (5)
C6—C7—C8—C14172.6 (4)C35—C29—C30—C31179.0 (4)
C6—C7—C8—C950.2 (6)C28—C29—C30—C3155.1 (6)
C7—C8—C9—C11177.6 (4)C25—C26—C31—C2254.9 (6)
C14—C8—C9—C1153.1 (5)C27—C26—C31—C22177.2 (5)
C7—C8—C9—C1052.3 (5)C25—C26—C31—C3964.6 (6)
C14—C8—C9—C10176.7 (4)C27—C26—C31—C3963.3 (6)
C2—C1—C10—C1866.3 (6)C25—C26—C31—C30173.5 (4)
C2—C1—C10—C9171.7 (5)C27—C26—C31—C3058.6 (6)
C2—C1—C10—C555.1 (6)C23—C22—C31—C2655.4 (6)
C8—C9—C10—C1867.6 (5)C23—C22—C31—C3966.0 (6)
C11—C9—C10—C1861.0 (6)C23—C22—C31—C30172.6 (5)
C8—C9—C10—C1170.4 (4)C32—C30—C31—C26173.7 (5)
C11—C9—C10—C161.0 (5)C29—C30—C31—C2656.9 (5)
C8—C9—C10—C553.9 (5)C32—C30—C31—C2257.1 (6)
C11—C9—C10—C5177.5 (4)C29—C30—C31—C22173.5 (4)
C6—C5—C10—C1863.9 (6)C32—C30—C31—C3963.4 (6)
C4—C5—C10—C1865.8 (6)C29—C30—C31—C3966.0 (6)
C6—C5—C10—C1175.4 (5)C29—C30—C32—C3352.4 (6)
C4—C5—C10—C154.9 (5)C31—C30—C32—C33178.7 (4)
C6—C5—C10—C956.8 (5)C30—C32—C33—C3454.9 (6)
C4—C5—C10—C9173.5 (4)C32—C33—C34—C3556.3 (6)
C8—C9—C11—C1253.4 (6)C32—C33—C34—C38167.3 (5)
C10—C9—C11—C12176.7 (4)C32—C33—C34—C4068.0 (6)
C9—C11—C12—C1354.2 (6)C28—C29—C35—C34179.1 (4)
C11—C12—C13—C17164.2 (5)C30—C29—C35—C3456.4 (5)
C11—C12—C13—C1453.7 (6)C28—C29—C35—C3655.0 (6)
C11—C12—C13—C1970.6 (5)C30—C29—C35—C36177.7 (5)
C7—C8—C14—C1551.1 (6)C33—C34—C35—C2959.9 (6)
C9—C8—C14—C15175.4 (4)C38—C34—C35—C29179.3 (4)
C7—C8—C14—C13178.1 (4)C40—C34—C35—C2962.7 (6)
C9—C8—C14—C1357.6 (5)C33—C34—C35—C36166.1 (5)
C12—C13—C14—C858.1 (6)C38—C34—C35—C3645.3 (5)
C17—C13—C14—C8179.1 (4)C40—C34—C35—C3671.3 (6)
C19—C13—C14—C865.3 (6)C29—C35—C36—C37158.6 (5)
C12—C13—C14—C15167.4 (5)C34—C35—C36—C3727.8 (6)
C17—C13—C14—C1546.4 (5)C35—C36—C37—C380.5 (6)
C19—C13—C14—C1569.2 (5)C35—C36—C37—Br2124.0 (4)
C8—C14—C15—C16161.2 (4)C36—C37—C38—O6153.6 (5)
C13—C14—C15—C1629.5 (5)Br2—C37—C38—O682.7 (5)
C14—C15—C16—C171.1 (6)C36—C37—C38—C3428.5 (6)
C14—C15—C16—Br1120.7 (4)Br2—C37—C38—C34152.2 (4)
C12—C13—C17—O372.5 (6)C33—C34—C38—O678.4 (6)
C14—C13—C17—O3171.5 (5)C35—C34—C38—O6165.9 (4)
C19—C13—C17—O353.6 (6)C40—C34—C38—O646.6 (7)
C12—C13—C17—C16160.8 (4)C33—C34—C38—C37160.7 (5)
C14—C13—C17—C1644.8 (5)C35—C34—C38—C3745.0 (5)
C19—C13—C17—C1673.1 (5)C40—C34—C38—C3774.3 (6)
C15—C16—C17—O3156.7 (5)O2—C20—O1—C33.7 (9)
Br1—C16—C17—O380.4 (5)C21—C20—O1—C3174.9 (5)
C15—C16—C17—C1327.6 (5)C2—C3—O1—C20157.4 (5)
Br1—C16—C17—C13150.5 (3)C4—C3—O1—C2079.5 (6)
C31—C22—C23—C2456.6 (7)O5—C41—O4—C242.3 (10)
C22—C23—C24—O4175.1 (4)C42—C41—O4—C24176.1 (5)
C22—C23—C24—C2555.2 (7)C23—C24—O4—C41146.1 (6)
O4—C24—C25—C26174.0 (5)C25—C24—O4—C4191.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O6i0.822.122.936 (6)179
O6—H6···O5ii0.821.972.757 (6)160
C16—H16···O6i0.982.563.347 (7)137
C23—H22A···Br1iii0.972.923.868 (6)166
C37—H37···Br1iv0.982.873.788 (6)156
Symmetry codes: (i) x, y, z1; (ii) x+2, y+1/2, z+2; (iii) x+1, y+1/2, z+1; (iv) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC21H33BrO3
Mr413.38
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)11.1010 (12), 7.6637 (8), 24.383 (3)
β (°) 93.036 (2)
V3)2071.5 (4)
Z4
Radiation typeMo Kα
µ (mm1)2.00
Crystal size (mm)0.26 × 0.18 × 0.12
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.624, 0.795
No. of measured, independent and
observed [I > 2σ(I)] reflections
13607, 9114, 3737
Rint0.042
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.125, 0.87
No. of reflections9114
No. of parameters459
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.29
Absolute structureFlack (1983), 3537 Friedel pairs
Absolute structure parameter0.016 (9)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O6i0.822.122.936 (6)179
O6—H6···O5ii0.821.972.757 (6)160
C16—H16···O6i0.982.563.347 (7)137
C23—H22A···Br1iii0.972.923.868 (6)166
C37—H37···Br1iv0.982.873.788 (6)156
Symmetry codes: (i) x, y, z1; (ii) x+2, y+1/2, z+2; (iii) x+1, y+1/2, z+1; (iv) x, y, z+1.
 

Acknowledgements

The authors gratefully acknowledge computing time provided by the X-ray Diffraction Analysis Centre of Key Laboratory of Medicinal Chemistry for Natural Resources (Ministry of Education), Yunnan University.

References

First citationAuer, U. (2007). Vet. J. 173, 422–427.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFajkos, J. & Sanda, V. (1962). Collect. Czech. Chem. Commun. 27, 355–358.  CAS Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTuba, Z., Maho, S. & Vizi, S. (2002). Curr. Med. Chem. 9, 1507–1536.  Web of Science CrossRef PubMed CAS Google Scholar

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