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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2956.
Published online 2010 October 30. doi:  10.1107/S1600536810042698
PMCID: PMC3009192

2-(5-Bromo-2-methyl­phen­yl)propan-2-ol

Abstract

The title compound, C10H13BrO, crystallizes with four independent mol­ecules of similar geometry in the asymmetric unit. The crystal packing is stabilized by inter­molecular O—H(...)O hydrogen bonds, which link the mol­ecules into tetra­mers.

Related literature

The title compound is an inter­mediate for the synthesis of SGLT2 inhibitors, which possess potent anti­hyperglycemic activity, see: Gao et al. (2010 [triangle]); Meng et al. (2008 [triangle]); Wang et al. (2010 [triangle]).

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Object name is e-66-o2956-scheme1.jpg

Experimental

Crystal data

  • C10H13BrO
  • M r = 229.11
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2956-efi1.jpg
  • a = 12.074 (2) Å
  • b = 12.115 (2) Å
  • c = 15.242 (3) Å
  • α = 109.51 (3)°
  • β = 103.52 (3)°
  • γ = 90.70 (3)°
  • V = 2033.2 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 4.00 mm−1
  • T = 113 K
  • 0.26 × 0.20 × 0.18 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 [triangle]) T min = 0.423, T max = 0.533
  • 20930 measured reflections
  • 7162 independent reflections
  • 5048 reflections with I > 2σ(I)
  • R int = 0.077

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.102
  • S = 0.94
  • 7162 reflections
  • 450 parameters
  • H-atom parameters constrained
  • Δρmax = 1.36 e Å−3
  • Δρmin = −1.06 e Å−3

Data collection: CrystalClear (Rigaku, 2007 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536810042698/rz2503sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042698/rz2503Isup2.hkl

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

supplementary crystallographic information

Comment

The title compound, whose crystal structure is reported herein, is an important intermediate for the synthesis of SGLT2 inhibitors possessing potent antihyperglycemic activity (Gao et al., 2010; Meng et al., 2008; Wang et al., 2010).

The asymmetric unit of the title compound consists of four independent molecules of similar geometry (Fig. 1). All bond lengths and angles are not unusual. In the crystal packing, the independent molecules are linked by intermolecular O—H···O hydrogen bonds into tetramers (Table 1).

Experimental

A dried 100-ml round-bottomed flask was charged with 2.43 g (10 mmol) of ethyl 5-bromo-2-methylbenzoate, 30 ml of dried THF and a magnetic bar, flushed with nitrogen and sealed with rubber septum. The flask was cooled with an ice-water bath, then stirring was initiated. Into the flask was slowly added 7.0 ml (21 mmol; 3.0 M in THF) of methyl magnesium chloride through syringe. After addition, the reaction mixture was stirred at this temperature for half an hour. The reaction mixture was poured into 200 ml of cooled water followed by addition of 200 ml of dichloromethane, and the reaction mixture was stirred and filtered off through a pad of celite. The filtrate was collected and the organic phase was separated. The aqueous phase was back-extracted with another 100 ml of dichloromethane, and the combined extracts were washed with saturated brine, dried over sodium sulfate and evaporated on a rotary evaporator to afford the crude product as a white solid, which was triturated with petroleum ether to furnish the pure product as colourless crystals after drying in vacuo at room temperature. Crystals suitable for diffraction were obtained by slow evaporation of a solution of the title compound in petroleum ether/dichloromethane (1:5 v/v) at room temperature.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95–0.98 Å, O—H = 0.84 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C, O) for methyl and hydroxyl H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels and 40% probability displacement ellipsoids for non-H atoms.
Fig. 2.
Top view of the tetramer formed by intermolecular O—H···O hydrogen bonds (dashed lines). Symmetry codes: (i) 1+x, 1+y, z; (ii) 1-x, 1-y, 1-z; (iii) x, 1+y, z.

Crystal data

C10H13BrOZ = 8
Mr = 229.11F(000) = 928
Triclinic, P1Dx = 1.497 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.074 (2) ÅCell parameters from 5648 reflections
b = 12.115 (2) Åθ = 1.7–27.9°
c = 15.242 (3) ŵ = 4.00 mm1
α = 109.51 (3)°T = 113 K
β = 103.52 (3)°Block, colourless
γ = 90.70 (3)°0.26 × 0.20 × 0.18 mm
V = 2033.2 (7) Å3

Data collection

Rigaku Saturn CCD area-detector diffractometer7162 independent reflections
Radiation source: rotating anode5048 reflections with I > 2σ(I)
confocalRint = 0.077
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 1.5°
ω and [var phi] scansh = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)k = −14→14
Tmin = 0.423, Tmax = 0.533l = −18→18
20930 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.102w = 1/[σ2(Fo2) + (0.0407P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.050
7162 reflectionsΔρmax = 1.36 e Å3
450 parametersΔρmin = −1.05 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0140 (5)

Special details

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)

xyzUiso*/Ueq
Br11.20641 (4)0.55935 (4)0.04617 (3)0.04051 (17)
Br20.34327 (4)0.53660 (4)0.47320 (4)0.04298 (17)
Br30.48759 (4)0.22317 (4)0.56556 (4)0.04416 (17)
Br40.46999 (4)0.38992 (5)0.06139 (4)0.05014 (19)
O10.8786 (2)0.9073 (2)0.2449 (2)0.0251 (7)
H10.93480.94840.24440.038*
O20.0633 (2)0.0422 (2)0.2459 (2)0.0276 (7)
H20.02420.09810.24220.041*
O30.2597 (2)−0.0834 (2)0.7560 (2)0.0264 (7)
H30.2269−0.02180.76060.040*
O40.9259 (2)0.2213 (2)0.2509 (2)0.0300 (7)
H40.86950.17870.24920.045*
C11.1312 (3)0.6251 (3)0.1462 (3)0.0216 (10)
C21.1757 (3)0.6195 (3)0.2360 (3)0.0269 (10)
H2A1.24300.58190.24930.032*
C31.1191 (3)0.6705 (3)0.3065 (3)0.0282 (11)
H3A1.14900.66730.36890.034*
C41.0203 (3)0.7263 (3)0.2901 (3)0.0214 (10)
C50.9755 (3)0.7312 (3)0.1972 (3)0.0173 (9)
C61.0333 (3)0.6798 (3)0.1268 (3)0.0202 (9)
H61.00470.68230.06400.024*
C70.8679 (3)0.7921 (3)0.1722 (3)0.0203 (9)
C80.7608 (3)0.7233 (3)0.1740 (3)0.0279 (10)
H8A0.77140.71490.23710.042*
H8B0.74900.64520.12400.042*
H8C0.69380.76610.16190.042*
C90.8479 (3)0.8080 (4)0.0753 (3)0.0284 (11)
H9A0.78170.85270.06630.043*
H9B0.83330.73070.02410.043*
H9C0.91590.85080.07290.043*
C100.9676 (4)0.7776 (4)0.3746 (3)0.0337 (11)
H10A0.89650.72970.36400.051*
H10B0.95100.85840.38060.051*
H10C1.02140.77780.43380.051*
C110.3139 (3)0.3892 (3)0.3709 (3)0.0257 (10)
C120.3457 (3)0.3765 (4)0.2870 (3)0.0324 (12)
H120.38530.43970.27960.039*
C130.3173 (3)0.2680 (4)0.2141 (3)0.0293 (11)
H130.33860.25800.15590.035*
C140.2595 (3)0.1730 (4)0.2214 (3)0.0235 (10)
C150.2295 (3)0.1867 (3)0.3085 (3)0.0183 (9)
C160.2580 (3)0.2966 (3)0.3821 (3)0.0207 (9)
H160.23840.30760.44110.025*
C170.1661 (3)0.0865 (3)0.3240 (3)0.0220 (10)
C180.2385 (3)−0.0160 (4)0.3225 (3)0.0309 (11)
H18A0.1957−0.07760.33310.046*
H18B0.30960.01150.37350.046*
H18C0.2567−0.04790.26000.046*
C190.1280 (4)0.1253 (4)0.4174 (3)0.0323 (11)
H19A0.08100.19110.41960.049*
H19B0.19550.15040.47220.049*
H19C0.08310.05940.42050.049*
C200.2293 (4)0.0606 (4)0.1338 (3)0.0371 (12)
H20A0.23120.07880.07610.056*
H20B0.15240.02630.12670.056*
H20C0.28490.00430.14210.056*
C210.4838 (3)0.1617 (4)0.6641 (3)0.0239 (10)
C220.5489 (3)0.2199 (4)0.7562 (3)0.0259 (10)
H220.59650.29000.77100.031*
C230.5432 (3)0.1731 (4)0.8269 (3)0.0253 (10)
H230.58870.21240.89040.030*
C240.4740 (3)0.0717 (3)0.8092 (3)0.0211 (9)
C250.4076 (3)0.0124 (3)0.7140 (3)0.0185 (9)
C260.4141 (3)0.0585 (3)0.6426 (3)0.0219 (10)
H260.37050.01910.57850.026*
C270.3283 (3)−0.1005 (3)0.6868 (3)0.0215 (10)
C280.2452 (3)−0.1334 (4)0.5874 (3)0.0329 (11)
H28A0.1945−0.20350.57560.049*
H28B0.2885−0.15000.53830.049*
H28C0.1993−0.06790.58470.049*
C290.3978 (4)−0.2032 (3)0.6918 (3)0.0315 (11)
H29A0.4465−0.18460.75710.047*
H29B0.4458−0.21720.64620.047*
H29C0.3458−0.27390.67530.047*
C300.4746 (4)0.0326 (4)0.8945 (3)0.0331 (11)
H30A0.4922−0.04940.87910.050*
H30B0.39920.03940.90840.050*
H30C0.53290.08270.95090.050*
C310.6097 (3)0.4163 (4)0.1563 (3)0.0269 (10)
C320.6225 (4)0.5019 (4)0.2444 (3)0.0348 (12)
H320.56270.55000.25830.042*
C330.7253 (4)0.5166 (4)0.3131 (3)0.0356 (12)
H330.73550.57740.37370.043*
C340.8145 (4)0.4461 (4)0.2972 (3)0.0268 (10)
C350.8002 (3)0.3588 (3)0.2055 (3)0.0201 (9)
C360.6960 (3)0.3454 (4)0.1365 (3)0.0225 (10)
H360.68460.28630.07480.027*
C370.8929 (3)0.2772 (4)0.1789 (3)0.0257 (10)
C381.0005 (3)0.3467 (4)0.1813 (3)0.0326 (11)
H38A1.03300.40190.24670.049*
H38B0.98080.39060.13710.049*
H38C1.05680.29240.16150.049*
C390.8532 (4)0.1783 (4)0.0817 (3)0.0359 (12)
H39A0.91390.12590.07200.054*
H39B0.83590.21200.03040.054*
H39C0.78430.13340.08020.054*
C400.9194 (4)0.4674 (4)0.3803 (3)0.0411 (13)
H40A0.97710.52150.37570.062*
H40B0.95100.39250.37750.062*
H40C0.89800.50200.44120.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0292 (3)0.0346 (3)0.0496 (3)0.0067 (2)0.0175 (2)−0.0012 (3)
Br20.0500 (3)0.0189 (3)0.0533 (4)−0.0039 (2)0.0047 (3)0.0098 (2)
Br30.0583 (4)0.0459 (3)0.0442 (3)0.0046 (3)0.0202 (3)0.0312 (3)
Br40.0220 (3)0.0828 (4)0.0657 (4)0.0112 (3)0.0060 (3)0.0548 (3)
O10.0231 (16)0.0154 (16)0.0339 (18)0.0017 (12)0.0101 (14)0.0029 (14)
O20.0225 (16)0.0203 (16)0.0364 (18)0.0026 (12)−0.0010 (14)0.0108 (15)
O30.0236 (17)0.0216 (17)0.0432 (19)0.0088 (13)0.0158 (15)0.0178 (15)
O40.0218 (16)0.0284 (18)0.045 (2)0.0021 (13)0.0024 (15)0.0235 (15)
C10.018 (2)0.017 (2)0.028 (3)−0.0004 (17)0.0066 (19)0.005 (2)
C20.017 (2)0.019 (2)0.045 (3)0.0010 (18)0.002 (2)0.015 (2)
C30.027 (3)0.029 (3)0.031 (3)−0.003 (2)−0.003 (2)0.020 (2)
C40.021 (2)0.021 (2)0.021 (2)−0.0043 (18)0.0016 (19)0.0086 (19)
C50.016 (2)0.013 (2)0.023 (2)−0.0017 (16)0.0028 (18)0.0085 (18)
C60.021 (2)0.015 (2)0.020 (2)−0.0013 (17)0.0021 (19)0.0044 (19)
C70.018 (2)0.015 (2)0.027 (3)0.0045 (17)0.0034 (19)0.006 (2)
C80.022 (2)0.024 (2)0.036 (3)0.0010 (18)0.003 (2)0.011 (2)
C90.030 (3)0.037 (3)0.024 (3)0.010 (2)0.006 (2)0.017 (2)
C100.040 (3)0.035 (3)0.026 (3)0.003 (2)0.008 (2)0.011 (2)
C110.024 (2)0.017 (2)0.035 (3)0.0005 (18)0.000 (2)0.013 (2)
C120.019 (2)0.035 (3)0.060 (3)0.009 (2)0.014 (2)0.034 (3)
C130.025 (2)0.045 (3)0.034 (3)0.017 (2)0.014 (2)0.030 (3)
C140.018 (2)0.028 (3)0.027 (3)0.0094 (18)0.0054 (19)0.013 (2)
C150.012 (2)0.022 (2)0.025 (2)0.0068 (17)0.0049 (18)0.012 (2)
C160.021 (2)0.021 (2)0.025 (2)0.0061 (18)0.0068 (19)0.013 (2)
C170.022 (2)0.017 (2)0.028 (3)0.0024 (18)0.008 (2)0.009 (2)
C180.030 (3)0.024 (3)0.042 (3)0.0051 (19)0.005 (2)0.018 (2)
C190.034 (3)0.032 (3)0.038 (3)−0.002 (2)0.016 (2)0.017 (2)
C200.043 (3)0.047 (3)0.023 (3)0.015 (2)0.013 (2)0.010 (2)
C210.027 (2)0.030 (3)0.025 (3)0.008 (2)0.014 (2)0.017 (2)
C220.019 (2)0.024 (2)0.038 (3)0.0034 (18)0.008 (2)0.013 (2)
C230.022 (2)0.028 (3)0.022 (2)0.0008 (19)0.0010 (19)0.006 (2)
C240.021 (2)0.027 (2)0.020 (2)0.0048 (18)0.0071 (19)0.012 (2)
C250.018 (2)0.019 (2)0.021 (2)0.0081 (17)0.0044 (18)0.0093 (19)
C260.023 (2)0.022 (2)0.022 (2)0.0028 (18)0.0067 (19)0.008 (2)
C270.020 (2)0.020 (2)0.024 (2)0.0034 (18)0.0054 (19)0.007 (2)
C280.031 (3)0.029 (3)0.032 (3)−0.004 (2)0.000 (2)0.009 (2)
C290.033 (3)0.022 (2)0.041 (3)0.007 (2)0.013 (2)0.010 (2)
C300.036 (3)0.046 (3)0.021 (3)0.001 (2)0.002 (2)0.019 (2)
C310.023 (2)0.031 (3)0.032 (3)0.001 (2)0.008 (2)0.018 (2)
C320.036 (3)0.029 (3)0.056 (3)0.012 (2)0.023 (3)0.028 (3)
C330.055 (3)0.018 (3)0.038 (3)0.004 (2)0.024 (3)0.007 (2)
C340.034 (3)0.019 (2)0.025 (3)−0.0076 (19)0.004 (2)0.007 (2)
C350.023 (2)0.015 (2)0.023 (2)0.0002 (17)0.0035 (19)0.0101 (19)
C360.023 (2)0.028 (3)0.024 (2)0.0050 (19)0.010 (2)0.015 (2)
C370.020 (2)0.028 (3)0.033 (3)0.0036 (19)0.004 (2)0.016 (2)
C380.027 (3)0.032 (3)0.045 (3)0.004 (2)0.013 (2)0.019 (2)
C390.035 (3)0.028 (3)0.043 (3)0.008 (2)0.015 (2)0.006 (2)
C400.051 (3)0.038 (3)0.024 (3)−0.011 (2)−0.005 (2)0.007 (2)

Geometric parameters (Å, °)

Br1—C11.907 (4)C19—H19A0.9800
Br2—C111.901 (4)C19—H19B0.9800
Br3—C211.896 (4)C19—H19C0.9800
Br4—C311.891 (4)C20—H20A0.9800
O1—C71.445 (4)C20—H20B0.9800
O1—H10.8400C20—H20C0.9800
O2—C171.453 (4)C21—C221.376 (5)
O2—H20.8400C21—C261.396 (5)
O3—C271.451 (4)C22—C231.388 (5)
O3—H30.8400C22—H220.9500
O4—C371.456 (5)C23—C241.389 (5)
O4—H40.8400C23—H230.9500
C1—C21.374 (6)C24—C251.417 (5)
C1—C61.382 (5)C24—C301.524 (5)
C2—C31.383 (5)C25—C261.395 (5)
C2—H2A0.9500C25—C271.538 (5)
C3—C41.391 (5)C26—H260.9500
C3—H3A0.9500C27—C291.522 (5)
C4—C51.414 (5)C27—C281.529 (5)
C4—C101.520 (5)C28—H28A0.9800
C5—C61.393 (5)C28—H28B0.9800
C5—C71.535 (5)C28—H28C0.9800
C6—H60.9500C29—H29A0.9800
C7—C91.517 (5)C29—H29B0.9800
C7—C81.541 (5)C29—H29C0.9800
C8—H8A0.9800C30—H30A0.9800
C8—H8B0.9800C30—H30B0.9800
C8—H8C0.9800C30—H30C0.9800
C9—H9A0.9800C31—C321.369 (6)
C9—H9B0.9800C31—C361.382 (5)
C9—H9C0.9800C32—C331.390 (6)
C10—H10A0.9800C32—H320.9500
C10—H10B0.9800C33—C341.397 (6)
C10—H10C0.9800C33—H330.9500
C11—C161.381 (5)C34—C351.413 (5)
C11—C121.381 (5)C34—C401.516 (6)
C12—C131.383 (6)C35—C361.407 (5)
C12—H120.9500C35—C371.538 (5)
C13—C141.389 (5)C36—H360.9500
C13—H130.9500C37—C381.527 (5)
C14—C151.413 (5)C37—C391.526 (5)
C14—C201.522 (5)C38—H38A0.9800
C15—C161.400 (5)C38—H38B0.9800
C15—C171.539 (5)C38—H38C0.9800
C16—H160.9500C39—H39A0.9800
C17—C191.525 (5)C39—H39B0.9800
C17—C181.525 (5)C39—H39C0.9800
C18—H18A0.9800C40—H40A0.9800
C18—H18B0.9800C40—H40B0.9800
C18—H18C0.9800C40—H40C0.9800
C7—O1—H1109.5H20A—C20—H20C109.5
C17—O2—H2109.5H20B—C20—H20C109.5
C27—O3—H3109.5C22—C21—C26120.8 (4)
C37—O4—H4109.5C22—C21—Br3119.6 (3)
C2—C1—C6121.2 (4)C26—C21—Br3119.6 (3)
C2—C1—Br1120.0 (3)C21—C22—C23118.1 (4)
C6—C1—Br1118.8 (3)C21—C22—H22120.9
C1—C2—C3117.7 (4)C23—C22—H22120.9
C1—C2—H2A121.1C24—C23—C22123.1 (4)
C3—C2—H2A121.1C24—C23—H23118.5
C2—C3—C4123.0 (4)C22—C23—H23118.5
C2—C3—H3A118.5C23—C24—C25118.2 (4)
C4—C3—H3A118.5C23—C24—C30117.1 (4)
C3—C4—C5118.7 (4)C25—C24—C30124.6 (4)
C3—C4—C10116.8 (4)C26—C25—C24118.8 (4)
C5—C4—C10124.5 (4)C26—C25—C27118.9 (3)
C6—C5—C4117.9 (3)C24—C25—C27122.3 (3)
C6—C5—C7119.5 (3)C25—C26—C21121.0 (4)
C4—C5—C7122.7 (3)C25—C26—H26119.5
C1—C6—C5121.6 (4)C21—C26—H26119.5
C1—C6—H6119.2O3—C27—C29107.0 (3)
C5—C6—H6119.2O3—C27—C28107.1 (3)
O1—C7—C9107.8 (3)C29—C27—C28109.5 (3)
O1—C7—C5108.8 (3)O3—C27—C25109.1 (3)
C9—C7—C5113.9 (3)C29—C27—C25110.7 (3)
O1—C7—C8106.9 (3)C28—C27—C25113.3 (3)
C9—C7—C8108.6 (3)C27—C28—H28A109.5
C5—C7—C8110.6 (3)C27—C28—H28B109.5
C7—C8—H8A109.5H28A—C28—H28B109.5
C7—C8—H8B109.5C27—C28—H28C109.5
H8A—C8—H8B109.5H28A—C28—H28C109.5
C7—C8—H8C109.5H28B—C28—H28C109.5
H8A—C8—H8C109.5C27—C29—H29A109.5
H8B—C8—H8C109.5C27—C29—H29B109.5
C7—C9—H9A109.5H29A—C29—H29B109.5
C7—C9—H9B109.5C27—C29—H29C109.5
H9A—C9—H9B109.5H29A—C29—H29C109.5
C7—C9—H9C109.5H29B—C29—H29C109.5
H9A—C9—H9C109.5C24—C30—H30A109.5
H9B—C9—H9C109.5C24—C30—H30B109.5
C4—C10—H10A109.5H30A—C30—H30B109.5
C4—C10—H10B109.5C24—C30—H30C109.5
H10A—C10—H10B109.5H30A—C30—H30C109.5
C4—C10—H10C109.5H30B—C30—H30C109.5
H10A—C10—H10C109.5C32—C31—C36121.0 (4)
H10B—C10—H10C109.5C32—C31—Br4119.8 (3)
C16—C11—C12121.2 (4)C36—C31—Br4119.2 (3)
C16—C11—Br2118.3 (3)C31—C32—C33118.1 (4)
C12—C11—Br2120.5 (3)C31—C32—H32121.0
C11—C12—C13117.3 (4)C33—C32—H32121.0
C11—C12—H12121.3C32—C33—C34123.2 (4)
C13—C12—H12121.3C32—C33—H33118.4
C12—C13—C14123.5 (4)C34—C33—H33118.4
C12—C13—H13118.3C33—C34—C35117.9 (4)
C14—C13—H13118.3C33—C34—C40117.6 (4)
C13—C14—C15118.5 (4)C35—C34—C40124.4 (4)
C13—C14—C20117.8 (4)C36—C35—C34118.3 (4)
C15—C14—C20123.7 (4)C36—C35—C37119.0 (3)
C16—C15—C14117.9 (4)C34—C35—C37122.7 (4)
C16—C15—C17119.6 (3)C31—C36—C35121.5 (4)
C14—C15—C17122.5 (4)C31—C36—H36119.2
C11—C16—C15121.5 (4)C35—C36—H36119.2
C11—C16—H16119.2O4—C37—C38106.8 (3)
C15—C16—H16119.2O4—C37—C39106.7 (3)
O2—C17—C19106.9 (3)C38—C37—C39109.5 (3)
O2—C17—C18107.5 (3)O4—C37—C35108.4 (3)
C19—C17—C18108.2 (3)C38—C37—C35111.2 (3)
O2—C17—C15108.6 (3)C39—C37—C35113.9 (3)
C19—C17—C15113.5 (3)C37—C38—H38A109.5
C18—C17—C15111.8 (3)C37—C38—H38B109.5
C17—C18—H18A109.5H38A—C38—H38B109.5
C17—C18—H18B109.5C37—C38—H38C109.5
H18A—C18—H18B109.5H38A—C38—H38C109.5
C17—C18—H18C109.5H38B—C38—H38C109.5
H18A—C18—H18C109.5C37—C39—H39A109.5
H18B—C18—H18C109.5C37—C39—H39B109.5
C17—C19—H19A109.5H39A—C39—H39B109.5
C17—C19—H19B109.5C37—C39—H39C109.5
H19A—C19—H19B109.5H39A—C39—H39C109.5
C17—C19—H19C109.5H39B—C39—H39C109.5
H19A—C19—H19C109.5C34—C40—H40A109.5
H19B—C19—H19C109.5C34—C40—H40B109.5
C14—C20—H20A109.5H40A—C40—H40B109.5
C14—C20—H20B109.5C34—C40—H40C109.5
H20A—C20—H20B109.5H40A—C40—H40C109.5
C14—C20—H20C109.5H40B—C40—H40C109.5
C6—C1—C2—C30.0 (6)C26—C21—C22—C23−0.1 (6)
Br1—C1—C2—C3178.8 (3)Br3—C21—C22—C23179.3 (3)
C1—C2—C3—C40.0 (6)C21—C22—C23—C24−0.8 (6)
C2—C3—C4—C50.0 (6)C22—C23—C24—C251.0 (6)
C2—C3—C4—C10179.7 (4)C22—C23—C24—C30−178.6 (4)
C3—C4—C5—C6−0.2 (5)C23—C24—C25—C26−0.3 (5)
C10—C4—C5—C6−179.9 (4)C30—C24—C25—C26179.3 (4)
C3—C4—C5—C7−179.2 (3)C23—C24—C25—C27−179.9 (3)
C10—C4—C5—C71.1 (6)C30—C24—C25—C27−0.4 (6)
C2—C1—C6—C5−0.2 (6)C24—C25—C26—C21−0.6 (6)
Br1—C1—C6—C5−178.9 (3)C27—C25—C26—C21179.1 (3)
C4—C5—C6—C10.2 (5)C22—C21—C26—C250.8 (6)
C7—C5—C6—C1179.3 (3)Br3—C21—C26—C25−178.7 (3)
C6—C5—C7—O1−130.5 (4)C26—C25—C27—O3−132.1 (3)
C4—C5—C7—O148.5 (5)C24—C25—C27—O347.6 (5)
C6—C5—C7—C9−10.3 (5)C26—C25—C27—C29110.5 (4)
C4—C5—C7—C9168.7 (4)C24—C25—C27—C29−69.9 (5)
C6—C5—C7—C8112.4 (4)C26—C25—C27—C28−12.9 (5)
C4—C5—C7—C8−68.6 (5)C24—C25—C27—C28166.7 (4)
C16—C11—C12—C131.1 (6)C36—C31—C32—C330.8 (6)
Br2—C11—C12—C13−177.4 (3)Br4—C31—C32—C33178.4 (3)
C11—C12—C13—C140.0 (6)C31—C32—C33—C34−1.8 (6)
C12—C13—C14—C15−1.2 (6)C32—C33—C34—C352.4 (6)
C12—C13—C14—C20177.3 (4)C32—C33—C34—C40−176.7 (4)
C13—C14—C15—C161.2 (5)C33—C34—C35—C36−1.9 (6)
C20—C14—C15—C16−177.2 (4)C40—C34—C35—C36177.1 (4)
C13—C14—C15—C17−179.6 (3)C33—C34—C35—C37179.1 (4)
C20—C14—C15—C172.0 (6)C40—C34—C35—C37−1.9 (6)
C12—C11—C16—C15−1.0 (6)C32—C31—C36—C35−0.4 (6)
Br2—C11—C16—C15177.5 (3)Br4—C31—C36—C35−178.0 (3)
C14—C15—C16—C11−0.2 (6)C34—C35—C36—C311.0 (6)
C17—C15—C16—C11−179.4 (4)C37—C35—C36—C31−180.0 (4)
C16—C15—C17—O2125.9 (4)C36—C35—C37—O4−126.0 (4)
C14—C15—C17—O2−53.3 (5)C34—C35—C37—O453.0 (5)
C16—C15—C17—C197.1 (5)C36—C35—C37—C38116.8 (4)
C14—C15—C17—C19−172.1 (4)C34—C35—C37—C38−64.2 (5)
C16—C15—C17—C18−115.7 (4)C36—C35—C37—C39−7.4 (5)
C14—C15—C17—C1865.1 (5)C34—C35—C37—C39171.6 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.841.902.742 (4)179
O2—H2···O4ii0.841.912.739 (4)170
O3—H3···O1iii0.841.902.727 (4)167
O4—H4···O3iv0.841.902.740 (4)179

Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2503).

References

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  • Wang, Z. F., Zhao, G. L., Liu, W., Wang, Y. L., Shao, H., Xu, W. R. & Tian, L. J. (2010). Chin. J. Org. Chem.30, 849–859.

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