Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o1181
doi:10.1107/S1600536812011634

(5-Bromo-2-hy­dr­oxy­phen­yl)(4-propyl­cyclo­hex­yl)methanone

Kang Meng,a Miao Cao,a Zhuo-Ling An,a Jie Zhanga and Li-Hong Liua*

aPharmacy Department of The Second Artillery General Hospital, Beijing 100088, People's Republic of China
*Correspondence e-mail: lihongliu2011@yahoo.cn

(Received 11 March 2012; accepted 17 March 2012; online 24 March 2012)

In the title compound, C16H21BrO2, the cyclo­hexane ring adopts a chair conformation. The hy­droxy and carbonyl groups are involved in an intra­molecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯O inter­actions link the mol­ecules into zigzag chains along [010].

Related literature

For details of the biological activity of SGLT2 inhibitors, see: 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.]); 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.]); Shao et al. (2011[Shao, H., Gao, Y. L., Lou, Y. Y., Wang, Y. L., Liu, W., Xu, W. R., Wang, J. W., Zhao, G. L. & Tang, L. D. (2011). Chin. J. Org. Chem. 31, 836-842.]). For related structures, see: Robinson et al. (2002[Robinson, P. D., Meyers, C. Y. & Kolb, V. M. (2002). Acta Cryst. E58, o1288-o1289.]); Wang et al. (2011[Wang, L., Chang, Z., Ding, C., Shao, H. & Sun, J. (2011). Acta Cryst. E67, o1173.]).

[Scheme 1]

Experimental

Crystal data

  • C16H21BrO2

  • Mr = 325.24

  • Monoclinic, P 21 /c

  • a = 14.5826 (12) Å

  • b = 8.5467 (8) Å

  • c = 12.6369 (10) Å

  • β = 113.037 (5)°

  • V = 1449.4 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.83 mm−1

  • T = 113 K

  • 0.20 × 0.18 × 0.12 mm
Data collection

  • Rigaku Saturn 724 CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2009[Rigaku/MSC (2009). CrystalClear-SM Expert. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.601, Tmax = 0.727

  • 17988 measured reflections

  • 3441 independent reflections

  • 3069 reflections with I > 2σ(I)

  • Rint = 0.035
Refinement

  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.062

  • S = 1.04

  • 3441 reflections

  • 177 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.81 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O2 0.81 (2) 1.82 (2) 2.5527 (16) 148 (3)
C3—H3⋯O1i 0.95 2.59 3.483 (2) 157
Symmetry code: (i) [-x+2, y-{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009[Rigaku/MSC (2009). CrystalClear-SM Expert. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812011634/cv5261sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812011634/cv5261Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812011634/cv5261Isup3.cml

checkCIF report


Comment top

SGLT2 inhibitors represent a new class of potential hypoglycemic agents (Meng et al., 2008). During the development of our own cyclohexane-bearing SGLT2 inhibitors (Gao et al., 2010; Shao et al., 2011), the title compound (I) was prepared as a key intermediate.

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously for related compounds (Robinson et al., 2002; Wang et al., 2011). The cyclohexane ring (C8—C13) adopts a chair conformation. Weak intermolecular C—H···O interactions (Table 1) link the molecules into zigzag chains in [010].

Related literature top

For details of the biological activity of SGLT2 inhibitors, see: Meng et al. (2008); Gao et al. (2010); Shao et al. (2011). For related structures, see: Robinson et al. (2002); Wang et al. (2011).

Experimental top

A dried 100-ml round-bottomed flask was charged with 1.89 g (10 mmol) of trans-4-propylcyclohexanecarboxylic acid chloride, 1.87 g (10 mmol) of 4-bromoanisole and 20 ml of dried dichloromethane. The mixture was stirred on an ice-water bath, followed by addition of 1.60 g (12 mmol) of anhydrous aluminium chloride in a portionwise manner. After addition, the reaction mixture was stirred at room temperature for 1 h and at reflux overnight, and poured into 300 ml of ice-water. The mixture thus formed was exacted with three 50-ml portions of dichloromethane, and the combined exacts were washed with saturated brine, dried over sodium sulfate and evaporated on a rotary evaporator to afford the crude title compound. Pure title compound was obtained by column chromatography. Crystals suitable for X-ray diffraction were obtained through slow evaporation of a solution of the pure title compound in dichloromethane/petroleum ether (1/30 by volume).

Refinement top

Hydroxy atom H1 was located on a difference map and isotropically refined. C-boundl H atoms were geometrically positioned [C–H = 0.95–1.00 Å], and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C) for the methyl H atoms.

Structure description top

SGLT2 inhibitors represent a new class of potential hypoglycemic agents (Meng et al., 2008). During the development of our own cyclohexane-bearing SGLT2 inhibitors (Gao et al., 2010; Shao et al., 2011), the title compound (I) was prepared as a key intermediate.

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously for related compounds (Robinson et al., 2002; Wang et al., 2011). The cyclohexane ring (C8—C13) adopts a chair conformation. Weak intermolecular C—H···O interactions (Table 1) link the molecules into zigzag chains in [010].

For details of the biological activity of SGLT2 inhibitors, see: Meng et al. (2008); Gao et al. (2010); Shao et al. (2011). For related structures, see: Robinson et al. (2002); Wang et al. (2011).

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009); cell refinement: CrystalClear-SM Expert (Rigaku/MSC, 2009); data reduction: CrystalClear-SM Expert (Rigaku/MSC, 2009); 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. View of the title compound, with displacement ellipsoids drawn at the 40% probability level.
(5-Bromo-2-hydroxyphenyl)(4-propylcyclohexyl)methanone top
Crystal data top
C16H21BrO2F(000) = 672
Mr = 325.24Dx = 1.490 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5072 reflections
a = 14.5826 (12) Åθ = 1.8–27.9°
b = 8.5467 (8) ŵ = 2.83 mm−1
c = 12.6369 (10) ÅT = 113 K
β = 113.037 (5)°Prism, colourless
V = 1449.4 (2) Å30.20 × 0.18 × 0.12 mm
Z = 4
Data collection top
Rigaku Saturn 724 CCD area-detector
diffractometer		3441 independent reflections
Radiation source: rotating anode3069 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.035
Detector resolution: 14.22 pixels mm-1θmax = 27.9°, θmin = 2.8°
ω and φ scansh = −19→19
Absorption correction: multi-scan
(CrystalClear-SM Expert; Rigaku/MSC, 2009)		k = −11→11
Tmin = 0.601, Tmax = 0.727l = −16→16
17988 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0334P)2 + 0.0947P]
where P = (Fo2 + 2Fc2)/3
3441 reflections(Δ/σ)max = 0.002
177 parametersΔρmax = 0.81 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Crystal data top
C16H21BrO2V = 1449.4 (2) Å3
Mr = 325.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.5826 (12) ŵ = 2.83 mm−1
b = 8.5467 (8) ÅT = 113 K
c = 12.6369 (10) Å0.20 × 0.18 × 0.12 mm
β = 113.037 (5)°
Data collection top
Rigaku Saturn 724 CCD area-detector
diffractometer		3441 independent reflections
Absorption correction: multi-scan
(CrystalClear-SM Expert; Rigaku/MSC, 2009)		3069 reflections with I > 2σ(I)
Tmin = 0.601, Tmax = 0.727Rint = 0.035
17988 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.062H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.81 e Å−3
3441 reflectionsΔρmin = −0.34 e Å−3
177 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
Br11.101943 (12)0.65152 (2)0.057741 (15)0.02149 (7)
O10.80421 (9)1.03963 (14)−0.31892 (10)0.0200 (3)
H10.759 (2)1.066 (3)−0.301 (2)0.058 (8)*
O20.69906 (9)1.05226 (14)−0.19829 (10)0.0202 (3)
C10.92537 (13)0.83440 (18)−0.04336 (14)0.0169 (3)
H1A0.91810.81600.02710.020*
C21.00541 (12)0.77214 (19)−0.06037 (14)0.0174 (3)
C31.01921 (13)0.8002 (2)−0.16215 (15)0.0197 (4)
H31.07470.7565−0.17330.024*
C40.95127 (13)0.8920 (2)−0.24620 (15)0.0193 (4)
H40.96100.9135−0.31480.023*
C50.86871 (13)0.95348 (19)−0.23174 (14)0.0170 (3)
C60.85425 (12)0.92496 (19)−0.12913 (14)0.0153 (3)
C70.76554 (12)0.99105 (19)−0.11519 (14)0.0157 (3)
C80.75600 (12)0.98403 (19)−0.00005 (13)0.0153 (3)
H80.82400.99460.06230.018*
C90.69103 (13)1.11868 (19)0.01104 (14)0.0174 (4)
H9A0.72211.21960.00530.021*
H9B0.62471.1133−0.05300.021*
C100.67844 (13)1.11146 (19)0.12561 (14)0.0169 (4)
H10A0.74401.12820.18930.020*
H10B0.63351.19680.12830.020*
C110.63570 (12)0.95477 (18)0.14288 (13)0.0154 (3)
H110.56750.94350.08120.018*
C120.70000 (13)0.82152 (19)0.12971 (14)0.0174 (4)
H12A0.66970.72050.13680.021*
H12B0.76680.82760.19280.021*
C130.71144 (13)0.82583 (19)0.01480 (14)0.0164 (3)
H13A0.64560.8109−0.04870.020*
H13B0.75560.73960.01160.020*
C140.62659 (13)0.9434 (2)0.25955 (14)0.0183 (4)
H14A0.59980.83890.26560.022*
H14B0.69420.95090.32110.022*
C150.56089 (13)1.0669 (2)0.28140 (15)0.0202 (4)
H15A0.49551.06920.21560.024*
H15B0.59231.17090.28690.024*
C160.54478 (14)1.0347 (2)0.39195 (15)0.0247 (4)
H16A0.50870.93590.38430.037*
H16B0.50591.12010.40560.037*
H16C0.60951.02760.45680.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01672 (10)0.02144 (10)0.02637 (11)0.00224 (7)0.00849 (8)0.00249 (7)
O10.0228 (7)0.0202 (6)0.0201 (6)0.0024 (5)0.0115 (6)0.0036 (5)
O20.0184 (6)0.0240 (6)0.0187 (6)0.0029 (5)0.0077 (5)0.0018 (5)
C10.0178 (8)0.0165 (8)0.0184 (8)−0.0028 (7)0.0094 (7)−0.0016 (7)
C20.0158 (8)0.0140 (8)0.0215 (9)−0.0014 (7)0.0063 (7)−0.0009 (7)
C30.0195 (9)0.0169 (8)0.0267 (9)−0.0027 (7)0.0135 (8)−0.0054 (7)
C40.0225 (9)0.0189 (8)0.0213 (9)−0.0041 (7)0.0139 (8)−0.0025 (7)
C50.0202 (9)0.0138 (8)0.0176 (8)−0.0040 (7)0.0079 (7)−0.0033 (7)
C60.0168 (8)0.0129 (8)0.0173 (8)−0.0028 (7)0.0080 (7)−0.0023 (6)
C70.0163 (8)0.0130 (8)0.0185 (8)−0.0029 (6)0.0075 (7)−0.0016 (7)
C80.0142 (8)0.0163 (8)0.0162 (8)−0.0005 (7)0.0069 (7)−0.0006 (6)
C90.0200 (9)0.0151 (8)0.0201 (9)0.0005 (7)0.0112 (7)0.0011 (7)
C100.0195 (9)0.0148 (8)0.0199 (9)0.0009 (7)0.0115 (7)−0.0007 (7)
C110.0155 (8)0.0158 (8)0.0150 (8)0.0009 (6)0.0061 (7)0.0003 (7)
C120.0192 (9)0.0152 (8)0.0198 (9)0.0020 (7)0.0098 (7)0.0039 (7)
C130.0179 (8)0.0146 (8)0.0185 (8)0.0006 (6)0.0089 (7)−0.0017 (7)
C140.0194 (9)0.0187 (8)0.0181 (8)−0.0002 (7)0.0089 (7)0.0014 (7)
C150.0205 (9)0.0218 (9)0.0202 (9)0.0020 (7)0.0100 (7)0.0006 (7)
C160.0285 (10)0.0260 (10)0.0245 (9)−0.0005 (8)0.0157 (8)−0.0008 (8)
Geometric parameters (Å, º) top
Br1—C21.9046 (17)C10—C111.528 (2)
O1—C51.353 (2)C10—H10A0.9900
O1—H10.81 (2)C10—H10B0.9900
O2—C71.233 (2)C11—C121.525 (2)
C1—C21.374 (2)C11—C141.534 (2)
C1—C61.403 (2)C11—H111.0000
C1—H1A0.9500C12—C131.525 (2)
C2—C31.398 (2)C12—H12A0.9900
C3—C41.379 (2)C12—H12B0.9900
C3—H30.9500C13—H13A0.9900
C4—C51.390 (2)C13—H13B0.9900
C4—H40.9500C14—C151.522 (2)
C5—C61.414 (2)C14—H14A0.9900
C6—C71.484 (2)C14—H14B0.9900
C7—C81.516 (2)C15—C161.530 (2)
C8—C91.531 (2)C15—H15A0.9900
C8—C131.543 (2)C15—H15B0.9900
C8—H81.0000C16—H16A0.9800
C9—C101.530 (2)C16—H16B0.9800
C9—H9A0.9900C16—H16C0.9800
C9—H9B0.9900
C5—O1—H1107.5 (19)C9—C10—H10B109.2
C2—C1—C6120.60 (15)H10A—C10—H10B107.9
C2—C1—H1A119.7C12—C11—C10109.65 (13)
C6—C1—H1A119.7C12—C11—C14110.22 (13)
C1—C2—C3120.96 (16)C10—C11—C14112.72 (13)
C1—C2—Br1119.98 (13)C12—C11—H11108.0
C3—C2—Br1119.03 (13)C10—C11—H11108.0
C4—C3—C2119.17 (16)C14—C11—H11108.0
C4—C3—H3120.4C11—C12—C13112.75 (13)
C2—C3—H3120.4C11—C12—H12A109.0
C3—C4—C5120.81 (16)C13—C12—H12A109.0
C3—C4—H4119.6C11—C12—H12B109.0
C5—C4—H4119.6C13—C12—H12B109.0
O1—C5—C4117.44 (15)H12A—C12—H12B107.8
O1—C5—C6122.35 (15)C12—C13—C8110.19 (13)
C4—C5—C6120.21 (16)C12—C13—H13A109.6
C1—C6—C5118.23 (15)C8—C13—H13A109.6
C1—C6—C7122.23 (15)C12—C13—H13B109.6
C5—C6—C7119.54 (15)C8—C13—H13B109.6
O2—C7—C6119.47 (14)H13A—C13—H13B108.1
O2—C7—C8119.83 (14)C15—C14—C11115.33 (14)
C6—C7—C8120.70 (14)C15—C14—H14A108.4
C7—C8—C9110.51 (13)C11—C14—H14A108.4
C7—C8—C13110.65 (13)C15—C14—H14B108.4
C9—C8—C13110.01 (13)C11—C14—H14B108.4
C7—C8—H8108.5H14A—C14—H14B107.5
C9—C8—H8108.5C14—C15—C16111.95 (14)
C13—C8—H8108.5C14—C15—H15A109.2
C10—C9—C8111.34 (13)C16—C15—H15A109.2
C10—C9—H9A109.4C14—C15—H15B109.2
C8—C9—H9A109.4C16—C15—H15B109.2
C10—C9—H9B109.4H15A—C15—H15B107.9
C8—C9—H9B109.4C15—C16—H16A109.5
H9A—C9—H9B108.0C15—C16—H16B109.5
C11—C10—C9112.15 (13)H16A—C16—H16B109.5
C11—C10—H10A109.2C15—C16—H16C109.5
C9—C10—H10A109.2H16A—C16—H16C109.5
C11—C10—H10B109.2H16B—C16—H16C109.5
C6—C1—C2—C31.4 (3)O2—C7—C8—C9−27.0 (2)
C6—C1—C2—Br1179.29 (12)C6—C7—C8—C9152.95 (14)
C1—C2—C3—C40.1 (3)O2—C7—C8—C1395.07 (18)
Br1—C2—C3—C4−177.77 (13)C6—C7—C8—C13−84.95 (18)
C2—C3—C4—C5−1.4 (3)C7—C8—C9—C10178.66 (13)
C3—C4—C5—O1−178.60 (15)C13—C8—C9—C1056.18 (18)
C3—C4—C5—C61.2 (3)C8—C9—C10—C11−56.10 (18)
C2—C1—C6—C5−1.6 (2)C9—C10—C11—C1254.50 (18)
C2—C1—C6—C7178.51 (15)C9—C10—C11—C14177.69 (14)
O1—C5—C6—C1−179.88 (15)C10—C11—C12—C13−55.68 (18)
C4—C5—C6—C10.3 (2)C14—C11—C12—C13179.67 (14)
O1—C5—C6—C70.0 (2)C11—C12—C13—C857.25 (18)
C4—C5—C6—C7−179.81 (15)C7—C8—C13—C12−178.73 (13)
C1—C6—C7—O2−170.67 (15)C9—C8—C13—C12−56.33 (17)
C5—C6—C7—O29.5 (2)C12—C11—C14—C15−177.88 (14)
C1—C6—C7—C89.3 (2)C10—C11—C14—C1559.25 (19)
C5—C6—C7—C8−170.52 (15)C11—C14—C15—C16172.51 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.81 (2)1.82 (2)2.5527 (16)148 (3)
C3—H3···O1i0.952.593.483 (2)157
Symmetry code: (i) −x+2, y−1/2, −z−1/2.

Experimental details

Crystal data
Chemical formulaC16H21BrO2
Mr325.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)14.5826 (12), 8.5467 (8), 12.6369 (10)
β (°) 113.037 (5)
V (Å3)1449.4 (2)
Z4
Radiation typeMo Kα
µ (mm−1)2.83
Crystal size (mm)0.20 × 0.18 × 0.12
Data collection
DiffractometerRigaku Saturn 724 CCD area-detector
Absorption correctionMulti-scan
(CrystalClear-SM Expert; Rigaku/MSC, 2009)
Tmin, Tmax0.601, 0.727
No. of measured, independent and
observed [I > 2σ(I)] reflections		17988, 3441, 3069
Rint0.035
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.062, 1.04
No. of reflections3441
No. of parameters177
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.81, −0.34

Computer programs: CrystalClear-SM Expert (Rigaku/MSC, 2009), 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···O20.81 (2)1.82 (2)2.5527 (16)148 (3)
C3—H3···O1i0.952.593.483 (2)156.9
Symmetry code: (i) −x+2, y−1/2, −z−1/2.
 

Acknowledgements

The authors thank Dr Haibin Song, Nankai University, for the X-ray crystallographic determination.

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 Google Scholar
 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 Google Scholar
 First citationRigaku/MSC (2009). CrystalClear-SM Expert. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
 First citationRobinson, P. D., Meyers, C. Y. & Kolb, V. M. (2002). Acta Cryst. E58, o1288–o1289.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationShao, H., Gao, Y. L., Lou, Y. Y., Wang, Y. L., Liu, W., Xu, W. R., Wang, J. W., Zhao, G. L. & Tang, L. D. (2011). Chin. J. Org. Chem. 31, 836–842.  CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, L., Chang, Z., Ding, C., Shao, H. & Sun, J. (2011). Acta Cryst. E67, o1173.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o1181
doi:10.1107/S1600536812011634
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS