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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 3| March 2011| Page o732
doi:10.1107/S1600536811006271

(E)-1-(2,4-Dihy­dr­oxy­phen­yl)-3-(4-hy­droxy­phen­yl)prop-2-en-1-one monohydrate

Jian-Guo Wang,a,b* Lin Wu,a Chan-Juan Zhong,b Zhao-Hui Ouyanga and De-Lian Yia

aApplied Chemistry Research Institute, Wuhan University of Science & Technology, Wuhan 430081, People's Republic of China, and bSchool of Chemistry & Chemical Engineering, Jiujiang University, Jiujiang 332005, People's Republic of China
*Correspondence e-mail: jgwang117@163.com

(Received 12 February 2011; accepted 19 February 2011; online 26 February 2011)

In the title compound, C15H12O4·H2O, the two benzene rings are not coplanar, making a dihedral angle of 7.24 (16)°. An intra­molecular hy­droxy–carbonyl O—H⋯O hydrogen bond occurs. In the crystal, four inter­molecular O—H⋯O hydrogen bonds involving the hy­droxy residues, the carbonyl group and the water mol­ecule lead to the formation of a three-dimensional network. The supra­molecular structure is further stabilized by weak C—H⋯O inter­actions.

Related literature

For the biological activity of the title compound, see: Jang et al. (2008[Jang, E. Y., Choe, E. S., Hwang, M., Kim, S. C., Lee, J. R., Kim, S. G., Jeon, J. P., Buono, R. J. & Yang, C. H. (2008). Eur. J. Pharmacol. 587, 124-128.]); Liu et al. (2008[Liu, B., Yang, J., Wen, Q. S. & Li, Y. (2008). Eur. J. Pharmacol. 587, 257-266]). For a related structure, see: Ma et al. (2005[Ma, C.-J., Li, G.-S., Zhang, D.-L., Liu, K. & Fan, X. (2005). J. Chromatogr. A, 1078, 188-192.]).

[Scheme 1]

Experimental

Crystal data

  • C15H12O4·H2O

  • Mr = 274.26

  • Monoclinic, P 21 /c

  • a = 11.489 (2) Å

  • b = 9.5903 (17) Å

  • c = 12.498 (2) Å

  • β = 103.649 (3)°

  • V = 1338.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 298 K

  • 0.12 × 0.10 × 0.10 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.988, Tmax = 0.990

  • 8297 measured reflections

  • 2625 independent reflections

  • 2115 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.144

  • S = 1.09

  • 2625 reflections

  • 196 parameters

  • 5 restraints

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

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1A⋯O3 0.87 (2) 1.74 (2) 2.530 (2) 150 (3)
O2—H2A⋯O5i 0.82 (2) 1.83 (2) 2.644 (3) 175 (4)
O4—H4A⋯O3ii 0.83 (2) 1.95 (2) 2.776 (2) 175 (4)
O5—H5A⋯O1iii 0.84 (2) 1.99 (2) 2.802 (2) 164 (3)
O5—H5B⋯O4iv 0.84 (2) 1.97 (2) 2.785 (3) 165 (3)
C9—H9⋯O4v 0.93 2.56 3.402 (3) 151
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]; (iii) -x, -y+2, -z; (iv) -x+1, -y+1, -z; (v) [-x+1, y+{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006271/go2004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006271/go2004Isup2.hkl

checkCIF report


Comment top

The title compound exhibits many biological activities such as tracheal relaxation effects (Liu et al., 2008) and suppressing cocaine-induced extracellular dopamine release (Jang et al., 2008).

One (E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one molecule bears one crystalline water molecule (Fig.1). In the molecule, the two benzene rings are not coplanar, the dihedral angle being 7.24 (16)°. The structure displays O—H···O and C—H···O hydrogen bonding (Table 1 and Fig. 2).

Related literature top

For the biological activity of the title compound, see: Jang et al. (2008); Liu et al. (2008). For a related structure, see: Ma et al. (2005).

Experimental top

2, 4-dihydroxyacetophenone (7.6 g, 0.05 mol) and 4-hydroxybenzaldehyde (8.54 g, 0.07 mol) were dissolved in diglycol (25 ml). Then 40% aq. KOH (50 ml) was added, and the reaction mixture was vigorously stirred under nitrogen atmosphere at 333 K for 2 h. The progress of the reaction was monitored by thin- layer chromatography (Si gel, developing solvent V(ethyl acetate)/V(benzene) = 1:2). The mixture was colled to room temperature and 1:1 (v/v) hydrochloric acid was added to acidize the mixture to pH=3 and a solid was obtained. After crystallized by ethanol-water, crystalline yellow needles were obtained, m.p. 472.5–474.2 K.

Refinement top

All the carbon-bounded hydrogen atoms were located at their ideal positions with the C—H=0.93Å and Uiso(H)=1.2Ueq(C). All the hydrogen atoms bonded to the oxygen atoms were located from the difference maps and refined with the restraints of O—H=0.82 (1)Å and Uiso(H)=1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing for (I), with O—H···O and C—H···O interactions shown as dashed lines.
(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one monohydrate top
Crystal data top
C15H12O4·H2OF(000) = 576
Mr = 274.26Dx = 1.361 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2288 reflections
a = 11.489 (2) Åθ = 2.7–25.3°
b = 9.5903 (17) ŵ = 0.10 mm−1
c = 12.498 (2) ÅT = 298 K
β = 103.649 (3)°Block, yellow
V = 1338.2 (4) Å30.12 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2625 independent reflections
Radiation source: fine-focus sealed tube2115 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
phi and ω scansθmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.988, Tmax = 0.990k = −11→9
8297 measured reflectionsl = −15→15
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0569P)2 + 0.499P]
where P = (Fo2 + 2Fc2)/3
2625 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.33 e Å−3
5 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C15H12O4·H2OV = 1338.2 (4) Å3
Mr = 274.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.489 (2) ŵ = 0.10 mm−1
b = 9.5903 (17) ÅT = 298 K
c = 12.498 (2) Å0.12 × 0.10 × 0.10 mm
β = 103.649 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2625 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2115 reflections with I > 2σ(I)
Tmin = 0.988, Tmax = 0.990Rint = 0.031
8297 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0575 restraints
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.33 e Å−3
2625 reflectionsΔρmin = −0.19 e Å−3
196 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
C10.19653 (18)1.0001 (2)0.07068 (17)0.0402 (5)
C20.10947 (18)1.1026 (2)0.07420 (17)0.0412 (5)
C30.0605 (2)1.1156 (2)0.16459 (19)0.0475 (6)
H30.00371.18440.16550.057*
C40.0950 (2)1.0275 (2)0.25329 (18)0.0452 (5)
C50.1818 (2)0.9256 (3)0.25306 (19)0.0500 (6)
H50.20610.86630.31310.060*
C60.2309 (2)0.9138 (2)0.16359 (19)0.0473 (6)
H60.28920.84620.16440.057*
C70.24678 (19)0.9881 (2)−0.02538 (18)0.0437 (5)
C80.3403 (2)0.8856 (3)−0.02910 (19)0.0494 (6)
H80.35880.81830.02580.059*
C90.3990 (2)0.8858 (3)−0.10772 (19)0.0493 (6)
H90.37510.9540−0.16130.059*
C100.49523 (19)0.7959 (2)−0.12387 (17)0.0431 (5)
C110.5467 (2)0.6925 (3)−0.05077 (19)0.0566 (7)
H110.51690.67600.01110.068*
C120.6406 (2)0.6134 (3)−0.0672 (2)0.0635 (7)
H120.67500.5458−0.01610.076*
C130.68407 (19)0.6350 (3)−0.16102 (18)0.0474 (6)
C140.6341 (2)0.7353 (3)−0.23509 (18)0.0486 (6)
H140.66280.7498−0.29780.058*
C150.5412 (2)0.8148 (3)−0.21662 (19)0.0518 (6)
H150.50800.8832−0.26750.062*
O10.07099 (15)1.19360 (19)−0.01001 (14)0.0589 (5)
H1A0.107 (3)1.171 (3)−0.061 (2)0.088*
O20.04269 (18)1.0443 (2)0.33756 (14)0.0649 (5)
H2A0.069 (3)0.988 (3)0.387 (2)0.097*
O30.21067 (14)1.06876 (19)−0.10709 (13)0.0565 (5)
O40.77775 (17)0.5545 (2)−0.17385 (14)0.0668 (6)
H4A0.784 (3)0.563 (4)−0.2384 (17)0.100*
O50.12061 (17)0.6281 (2)0.00416 (14)0.0587 (5)
H5A0.072 (2)0.687 (3)0.017 (3)0.088*
H5B0.149 (3)0.586 (3)0.0630 (19)0.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0381 (11)0.0444 (12)0.0430 (12)−0.0015 (9)0.0192 (9)−0.0060 (10)
C20.0413 (11)0.0446 (12)0.0415 (11)−0.0002 (10)0.0174 (9)0.0015 (10)
C30.0457 (12)0.0512 (14)0.0524 (13)0.0090 (11)0.0251 (10)−0.0011 (11)
C40.0502 (12)0.0514 (13)0.0409 (12)0.0005 (10)0.0247 (10)−0.0039 (10)
C50.0583 (14)0.0530 (14)0.0436 (12)0.0078 (11)0.0217 (11)0.0070 (10)
C60.0485 (12)0.0485 (13)0.0497 (13)0.0086 (10)0.0213 (10)−0.0007 (10)
C70.0400 (11)0.0520 (14)0.0432 (12)−0.0049 (10)0.0183 (9)−0.0041 (10)
C80.0513 (13)0.0551 (14)0.0483 (13)0.0061 (11)0.0249 (10)−0.0017 (11)
C90.0475 (12)0.0576 (15)0.0485 (13)0.0041 (11)0.0229 (10)0.0008 (11)
C100.0404 (11)0.0506 (13)0.0431 (12)−0.0005 (10)0.0193 (10)−0.0044 (10)
C110.0605 (15)0.0757 (18)0.0437 (13)0.0113 (13)0.0323 (12)0.0049 (12)
C120.0690 (16)0.0791 (19)0.0495 (14)0.0290 (15)0.0285 (12)0.0156 (13)
C130.0425 (12)0.0596 (15)0.0446 (12)0.0065 (11)0.0193 (10)−0.0039 (11)
C140.0493 (13)0.0617 (15)0.0427 (12)0.0062 (11)0.0267 (10)0.0028 (11)
C150.0528 (13)0.0586 (15)0.0507 (14)0.0097 (11)0.0254 (11)0.0083 (11)
O10.0648 (11)0.0665 (12)0.0538 (10)0.0202 (9)0.0307 (8)0.0141 (9)
O20.0793 (13)0.0756 (13)0.0531 (10)0.0183 (10)0.0424 (10)0.0072 (9)
O30.0571 (10)0.0710 (12)0.0492 (9)0.0108 (8)0.0284 (8)0.0084 (8)
O40.0654 (11)0.0920 (14)0.0512 (10)0.0355 (10)0.0302 (9)0.0110 (10)
O50.0702 (12)0.0605 (12)0.0539 (10)0.0151 (9)0.0315 (9)0.0043 (9)
Geometric parameters (Å, º) top
C1—C61.405 (3)C9—H90.9300
C1—C21.410 (3)C10—C111.383 (3)
C1—C71.454 (3)C10—C151.394 (3)
C2—O11.359 (3)C11—C121.374 (3)
C2—C31.382 (3)C11—H110.9300
C3—C41.375 (3)C12—C131.393 (3)
C3—H30.9300C12—H120.9300
C4—O21.340 (3)C13—C141.364 (3)
C4—C51.397 (3)C13—O41.364 (3)
C5—C61.371 (3)C14—C151.375 (3)
C5—H50.9300C14—H140.9300
C6—H60.9300C15—H150.9300
C7—O31.270 (3)O1—H1A0.867 (18)
C7—C81.465 (3)O2—H2A0.819 (18)
C8—C91.316 (3)O4—H4A0.829 (18)
C8—H80.9300O5—H5A0.836 (18)
C9—C101.453 (3)O5—H5B0.836 (18)
C6—C1—C2116.61 (18)C8—C9—H9115.0
C6—C1—C7123.2 (2)C10—C9—H9115.0
C2—C1—C7120.24 (19)C11—C10—C15117.1 (2)
O1—C2—C3117.03 (19)C11—C10—C9123.66 (19)
O1—C2—C1121.81 (18)C15—C10—C9119.2 (2)
C3—C2—C1121.2 (2)C12—C11—C10121.7 (2)
C4—C3—C2120.5 (2)C12—C11—H11119.1
C4—C3—H3119.7C10—C11—H11119.1
C2—C3—H3119.7C11—C12—C13119.6 (2)
O2—C4—C3117.5 (2)C11—C12—H12120.2
O2—C4—C5122.6 (2)C13—C12—H12120.2
C3—C4—C5119.90 (19)C14—C13—O4122.43 (19)
C6—C5—C4119.4 (2)C14—C13—C12119.9 (2)
C6—C5—H5120.3O4—C13—C12117.6 (2)
C4—C5—H5120.3C13—C14—C15119.7 (2)
C5—C6—C1122.4 (2)C13—C14—H14120.1
C5—C6—H6118.8C15—C14—H14120.1
C1—C6—H6118.8C14—C15—C10121.9 (2)
O3—C7—C1119.85 (19)C14—C15—H15119.0
O3—C7—C8119.07 (19)C10—C15—H15119.0
C1—C7—C8121.1 (2)C2—O1—H1A107 (2)
C9—C8—C7122.1 (2)C4—O2—H2A111 (3)
C9—C8—H8119.0C13—O4—H4A108 (2)
C7—C8—H8119.0H5A—O5—H5B107 (3)
C8—C9—C10130.0 (2)
C6—C1—C2—O1178.7 (2)C2—C1—C7—C8177.9 (2)
C7—C1—C2—O1−0.9 (3)O3—C7—C8—C98.8 (4)
C6—C1—C2—C3−0.5 (3)C1—C7—C8—C9−170.2 (2)
C7—C1—C2—C3179.9 (2)C7—C8—C9—C10178.4 (2)
O1—C2—C3—C4−179.8 (2)C8—C9—C10—C11−3.0 (4)
C1—C2—C3—C4−0.6 (3)C8—C9—C10—C15178.3 (3)
C2—C3—C4—O2−179.0 (2)C15—C10—C11—C121.3 (4)
C2—C3—C4—C51.1 (4)C9—C10—C11—C12−177.5 (2)
O2—C4—C5—C6179.5 (2)C10—C11—C12—C13−1.5 (4)
C3—C4—C5—C6−0.6 (4)C11—C12—C13—C140.7 (4)
C4—C5—C6—C1−0.5 (4)C11—C12—C13—O4179.7 (2)
C2—C1—C6—C51.1 (3)O4—C13—C14—C15−178.9 (2)
C7—C1—C6—C5−179.4 (2)C12—C13—C14—C150.1 (4)
C6—C1—C7—O3179.3 (2)C13—C14—C15—C10−0.3 (4)
C2—C1—C7—O3−1.1 (3)C11—C10—C15—C14−0.4 (4)
C6—C1—C7—C8−1.7 (3)C9—C10—C15—C14178.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O30.87 (2)1.74 (2)2.530 (2)150 (3)
O2—H2A···O5i0.82 (2)1.83 (2)2.644 (3)175 (4)
O4—H4A···O3ii0.83 (2)1.95 (2)2.776 (2)175 (4)
O5—H5A···O1iii0.84 (2)1.99 (2)2.802 (2)164 (3)
O5—H5B···O4iv0.84 (2)1.97 (2)2.785 (3)165 (3)
C9—H9···O4v0.932.563.402 (3)151
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y−1/2, −z−1/2; (iii) −x, −y+2, −z; (iv) −x+1, −y+1, −z; (v) −x+1, y+1/2, −z−1/2.

Experimental details

Crystal data
Chemical formulaC15H12O4·H2O
Mr274.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)11.489 (2), 9.5903 (17), 12.498 (2)
β (°) 103.649 (3)
V (Å3)1338.2 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.12 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.988, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections		8297, 2625, 2115
Rint0.031
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.144, 1.09
No. of reflections2625
No. of parameters196
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.33, −0.19

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O30.867 (18)1.74 (2)2.530 (2)150 (3)
O2—H2A···O5i0.819 (18)1.827 (19)2.644 (3)175 (4)
O4—H4A···O3ii0.829 (18)1.948 (19)2.776 (2)175 (4)
O5—H5A···O1iii0.836 (18)1.989 (19)2.802 (2)164 (3)
O5—H5B···O4iv0.836 (18)1.97 (2)2.785 (3)165 (3)
C9—H9···O4v0.932.563.402 (3)151
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, y−1/2, −z−1/2; (iii) −x, −y+2, −z; (iv) −x+1, −y+1, −z; (v) −x+1, y+1/2, −z−1/2.
 

Acknowledgements

This study was funded by the Jiangxi Provincial Department of Education (GJJ08433) and the Jiangxi Provincial Department of Science and Technology (2008ZD06100). The authors thank Professor Xianggao Meng at Hua-Zhong Normal University for the data acquisition.

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.  Google Scholar
 First citationJang, E. Y., Choe, E. S., Hwang, M., Kim, S. C., Lee, J. R., Kim, S. G., Jeon, J. P., Buono, R. J. & Yang, C. H. (2008). Eur. J. Pharmacol. 587, 124–128.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationLiu, B., Yang, J., Wen, Q. S. & Li, Y. (2008). Eur. J. Pharmacol. 587, 257–266  Web of Science CrossRef PubMed CAS Google Scholar
 First citationMa, C.-J., Li, G.-S., Zhang, D.-L., Liu, K. & Fan, X. (2005). J. Chromatogr. A, 1078, 188–192.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS 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.

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ISSN: 2056-9890
Volume 67| Part 3| March 2011| Page o732
doi:10.1107/S1600536811006271
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