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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aDepartment of Pathology, Chinese People's Armed Police Corps Hospital of Qinghai Province, Xining 810000, People's Republic of China, and bInstitute of Cardiovascular Disease, Pingjin Hospital, Medical College of Chinese People's Armed Police Forces, Tianjin 300162, People's Republic of China
*Correspondence e-mail: xinlin_liu2010@yahoo.cn

(Received 10 October 2010; accepted 20 October 2010; online 30 October 2010)

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[Gao, Y. L., Zhao, G. L., Liu, W., Wang, Y. L., Xu, W. R. & Wang, J. W. (2010). Chin. J. Chem. 28, 605-612.]); Meng et al. (2008[Meng, M., Ellsworth, B. A., Nirschl, A. A., McCann, P. J., Patel, M., Girotra, R. N., Wu, G., Sher, P. M., Morrison, E. P., Biller, S. A., Zahler, R., Deshpande, P. P., Pullockaran, A., Hagan, D. L., Morgan, N., Taylor, J. R., Obermeier, M. T., Humphreys, W. G., Khanna, A., Discenza, L., Robertson, J. M., Wang, A., Han, S., Wetterau, J. R., Janovitz, E. B., Flint, O. P., Whaley, J. M. & Washburn, W. N. (2008). J. Med. Chem. 51, 1145-1149.]); Wang et al. (2010[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.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13BrO

  • Mr = 229.11

  • Triclinic, [P \overline 1]

  • 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[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.423, Tmax = 0.533

  • 20930 measured reflections

  • 7162 independent reflections

  • 5048 reflections with I > 2σ(I)

  • Rint = 0.077

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2i 0.84 1.90 2.742 (4) 179
O2—H2⋯O4ii 0.84 1.91 2.739 (4) 170
O3—H3⋯O1iii 0.84 1.90 2.727 (4) 167
O4—H4⋯O3iv 0.84 1.90 2.740 (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.

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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

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).

Related literature top

The title compound is an intermediate for the synthesis of SGLT2

inhibitors, which possess potent antihyperglycemic activity, see: Gao et al. (2010); Meng et al. (2008); Wang et al. (2010).

Experimental top

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 top

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.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 40% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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.
2-(5-Bromo-2-methylphenyl)propan-2-ol top
Crystal data top
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 top
Rigaku Saturn CCD area-detector
diffractometer
7162 independent reflections
Radiation source: rotating anode5048 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.077
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 1.5°
ω and ϕ scansh = 1414
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
k = 1414
Tmin = 0.423, Tmax = 0.533l = 1818
20930 measured reflections
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.102 w = 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 = 1.06 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)
Crystal data top
C10H13BrOγ = 90.70 (3)°
Mr = 229.11V = 2033.2 (7) Å3
Triclinic, P1Z = 8
a = 12.074 (2) ÅMo Kα radiation
b = 12.115 (2) ŵ = 4.00 mm1
c = 15.242 (3) ÅT = 113 K
α = 109.51 (3)°0.26 × 0.20 × 0.18 mm
β = 103.52 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
7162 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2007)
5048 reflections with I > 2σ(I)
Tmin = 0.423, Tmax = 0.533Rint = 0.077
20930 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 0.94Δρmax = 1.36 e Å3
7162 reflectionsΔρmin = 1.06 e Å3
450 parameters
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
Br11.20641 (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)
H30.22690.02180.76060.040*
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)
H18A0.19570.07760.33310.046*
H18B0.30960.01150.37350.046*
H18C0.25670.04790.26000.046*
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)
H28A0.19450.20350.57560.049*
H28B0.28850.15000.53830.049*
H28C0.19930.06790.58470.049*
C290.3978 (4)0.2032 (3)0.6918 (3)0.0315 (11)
H29A0.44650.18460.75710.047*
H29B0.44580.21720.64620.047*
H29C0.34580.27390.67530.047*
C300.4746 (4)0.0326 (4)0.8945 (3)0.0331 (11)
H30A0.49220.04940.87910.050*
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) top
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, º) top
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—C230.1 (6)
Br1—C1—C2—C3178.8 (3)Br3—C21—C22—C23179.3 (3)
C1—C2—C3—C40.0 (6)C21—C22—C23—C240.8 (6)
C2—C3—C4—C50.0 (6)C22—C23—C24—C251.0 (6)
C2—C3—C4—C10179.7 (4)C22—C23—C24—C30178.6 (4)
C3—C4—C5—C60.2 (5)C23—C24—C25—C260.3 (5)
C10—C4—C5—C6179.9 (4)C30—C24—C25—C26179.3 (4)
C3—C4—C5—C7179.2 (3)C23—C24—C25—C27179.9 (3)
C10—C4—C5—C71.1 (6)C30—C24—C25—C270.4 (6)
C2—C1—C6—C50.2 (6)C24—C25—C26—C210.6 (6)
Br1—C1—C6—C5178.9 (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—C25178.7 (3)
C6—C5—C7—O1130.5 (4)C26—C25—C27—O3132.1 (3)
C4—C5—C7—O148.5 (5)C24—C25—C27—O347.6 (5)
C6—C5—C7—C910.3 (5)C26—C25—C27—C29110.5 (4)
C4—C5—C7—C9168.7 (4)C24—C25—C27—C2969.9 (5)
C6—C5—C7—C8112.4 (4)C26—C25—C27—C2812.9 (5)
C4—C5—C7—C868.6 (5)C24—C25—C27—C28166.7 (4)
C16—C11—C12—C131.1 (6)C36—C31—C32—C330.8 (6)
Br2—C11—C12—C13177.4 (3)Br4—C31—C32—C33178.4 (3)
C11—C12—C13—C140.0 (6)C31—C32—C33—C341.8 (6)
C12—C13—C14—C151.2 (6)C32—C33—C34—C352.4 (6)
C12—C13—C14—C20177.3 (4)C32—C33—C34—C40176.7 (4)
C13—C14—C15—C161.2 (5)C33—C34—C35—C361.9 (6)
C20—C14—C15—C16177.2 (4)C40—C34—C35—C36177.1 (4)
C13—C14—C15—C17179.6 (3)C33—C34—C35—C37179.1 (4)
C20—C14—C15—C172.0 (6)C40—C34—C35—C371.9 (6)
C12—C11—C16—C151.0 (6)C32—C31—C36—C350.4 (6)
Br2—C11—C16—C15177.5 (3)Br4—C31—C36—C35178.0 (3)
C14—C15—C16—C110.2 (6)C34—C35—C36—C311.0 (6)
C17—C15—C16—C11179.4 (4)C37—C35—C36—C31180.0 (4)
C16—C15—C17—O2125.9 (4)C36—C35—C37—O4126.0 (4)
C14—C15—C17—O253.3 (5)C34—C35—C37—O453.0 (5)
C16—C15—C17—C197.1 (5)C36—C35—C37—C38116.8 (4)
C14—C15—C17—C19172.1 (4)C34—C35—C37—C3864.2 (5)
C16—C15—C17—C18115.7 (4)C36—C35—C37—C397.4 (5)
C14—C15—C17—C1865.1 (5)C34—C35—C37—C39171.6 (4)
Hydrogen-bond geometry (Å, º) top
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) x1, y, z; (iii) x+1, y+1, z+1; (iv) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC10H13BrO
Mr229.11
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)12.074 (2), 12.115 (2), 15.242 (3)
α, β, γ (°)109.51 (3), 103.52 (3), 90.70 (3)
V3)2033.2 (7)
Z8
Radiation typeMo Kα
µ (mm1)4.00
Crystal size (mm)0.26 × 0.20 × 0.18
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2007)
Tmin, Tmax0.423, 0.533
No. of measured, independent and
observed [I > 2σ(I)] reflections
20930, 7162, 5048
Rint0.077
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.102, 0.94
No. of reflections7162
No. of parameters450
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.36, 1.06

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.841.902.742 (4)178.9
O2—H2···O4ii0.841.912.739 (4)170.3
O3—H3···O1iii0.841.902.727 (4)166.5
O4—H4···O3iv0.841.902.740 (4)179.0
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y, z; (iii) x+1, y+1, z+1; (iv) x+1, y, z+1.
 

References

First citationGao, Y. L., Zhao, G. L., Liu, W., Wang, Y. L., Xu, W. R. & Wang, J. W. (2010). Chin. J. Chem. 28, 605–612.  CrossRef CAS
First citationMeng, M., Ellsworth, B. A., Nirschl, A. A., McCann, P. J., Patel, M., Girotra, R. N., Wu, G., Sher, P. M., Morrison, E. P., Biller, S. A., Zahler, R., Deshpande, P. P., Pullockaran, A., Hagan, D. L., Morgan, N., Taylor, J. R., Obermeier, M. T., Humphreys, W. G., Khanna, A., Discenza, L., Robertson, J. M., Wang, A., Han, S., Wetterau, J. R., Janovitz, E. B., Flint, O. P., Whaley, J. M. & Washburn, W. N. (2008). J. Med. Chem. 51, 1145–1149.  Web of Science CrossRef PubMed CAS
First citationRigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWang, 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.  CAS

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