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In the title compound, C22H20Br2O5, the dihedral angle between the two benzene rings is 12.0 (3)°. The cyclo­hexa­none ring has an envelope conformation with the flap atom displaced by 0.675 (6) Å from the plane of the other five atoms. The crystal structure has intra- and inter­molecular hydrogen bonds between the hydr­oxy and meth­oxy groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027559/wn2146sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027559/wn2146Isup2.hkl
Contains datablock I

CCDC reference: 654958

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.110
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br2 .. O3 .. 3.05 Ang.
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Curcumin analogs exhibit potential antioxidative properties (Sardjiman et al., 1997, Youssef et al., 2004) and inhibitory activities on α-glucosidase (Du, Liu et al., 2006) and on aldose reductase (Du, Bao et al., 2006). The title compound, C22H20Br2O5, is a synthesized curcumin analog and we report here its crystal structure.

The X-ray crystallographic study of the title compound confirms the previously proposed molecular structure based on spectroscopic data (Fig. 1). The C—C, CC, C—O and CO distances show no remarkable features.

A structural feature is the presence of intermolecular O—H···O hydrogen bonds between the hydroxy groups and the methoxy groups O of neighboring molecules (Table 2), resulting in infinite chains along the c axis (Fig. 2). Furthermore, there is a short intermolecular contact between the carbonyl O atom and a Br atom; Br2···O3 = 3.051 (3) Å.

Related literature top

For related literature, see: Du, Bao et al. (2006); Du, Liu et al. (2006); Sardjiman et al. (1997); Youssef et al. (2004).

Experimental top

The title compound was synthesized as previously described (Du, Liu et al., 2006). A mixture of 3-bromo-4-hydroxy-5-methoxybenzaldehyde (0.01 mol) and cyclohexanone (0.005 mol) was dissolved in glacial acetic acid (10 ml) saturated with anhydrous hydrogen chloride and heated in a water bath at 25–30 °C for 2 h. After standing for 2 days, the mixture was treated with cold water and filtered to obtain a yellow solid. Crystals were obtained by recrystallization from acetic acid and water (1:1) The compound identity was confirmed by the 1H NMR spectra and ESI-MS. 1H NMR (DMSO-d6, 300 MHz) δ, 9.94 (br, 2H, –OH), 7.50 (s, 2H, –CH=), 7.27 (2H, aromatic), 7.13 (2H, aromatic), 3.86 (s, 6H, OCH3), 2.88 (t, J = 6.7 Hz, 4H, –CH2—C—CH2–), 1.73 (q, J = 6.7 Hz, 2H, –C—CH2—C–). ESI-MS (m/z):523[M]-.

Refinement top

All H atoms were positioned geometrically and refined in a riding model, with C—H = 0.98 Å for methyl, C—H = 0.99 Å for methylene, Csp2—H = 0.95 Å and O—H = 0.84 Å. Uiso(H) = xUeq(C), where x = 1.5 for methyl and 1.2 for other C; Uiso(H) = 1.5Ueq(O).

Structure description top

Curcumin analogs exhibit potential antioxidative properties (Sardjiman et al., 1997, Youssef et al., 2004) and inhibitory activities on α-glucosidase (Du, Liu et al., 2006) and on aldose reductase (Du, Bao et al., 2006). The title compound, C22H20Br2O5, is a synthesized curcumin analog and we report here its crystal structure.

The X-ray crystallographic study of the title compound confirms the previously proposed molecular structure based on spectroscopic data (Fig. 1). The C—C, CC, C—O and CO distances show no remarkable features.

A structural feature is the presence of intermolecular O—H···O hydrogen bonds between the hydroxy groups and the methoxy groups O of neighboring molecules (Table 2), resulting in infinite chains along the c axis (Fig. 2). Furthermore, there is a short intermolecular contact between the carbonyl O atom and a Br atom; Br2···O3 = 3.051 (3) Å.

For related literature, see: Du, Bao et al. (2006); Du, Liu et al. (2006); Sardjiman et al. (1997); Youssef et al. (2004).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the a axis, showing one chain of molecules connected by O—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted. [Symmetry code: (I) x,y,1 + z].
(2E,6E)-2,6-Bis(3-bromo-4-hydroxy-5-methoxybenzylidene)cyclohexanone top
Crystal data top
C22H20Br2O5F(000) = 1048
Mr = 524.20Dx = 1.744 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2576 reflections
a = 7.5550 (11) Åθ = 2.3–26.7°
b = 14.938 (2) ŵ = 4.09 mm1
c = 17.763 (3) ÅT = 173 K
β = 95.201 (3)°Needle, colorless
V = 1996.4 (5) Å30.32 × 0.12 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
4349 independent reflections
Radiation source: fine-focus sealed tube2760 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
φ and ω scansθmax = 27.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.354, Tmax = 0.685k = 1911
10131 measured reflectionsl = 2122
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0496P)2]
where P = (Fo2 + 2Fc2)/3
4349 reflections(Δ/σ)max = 0.001
266 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = 0.54 e Å3
Crystal data top
C22H20Br2O5V = 1996.4 (5) Å3
Mr = 524.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.5550 (11) ŵ = 4.09 mm1
b = 14.938 (2) ÅT = 173 K
c = 17.763 (3) Å0.32 × 0.12 × 0.10 mm
β = 95.201 (3)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
4349 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2760 reflections with I > 2σ(I)
Tmin = 0.354, Tmax = 0.685Rint = 0.052
10131 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.02Δρmax = 0.78 e Å3
4349 reflectionsΔρmin = 0.54 e Å3
266 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
Br10.34530 (7)0.66581 (3)0.31408 (3)0.03229 (16)
Br20.52599 (7)0.71802 (3)0.39084 (3)0.02742 (15)
C10.1939 (6)0.4930 (3)0.3194 (2)0.0212 (10)
C20.1366 (6)0.4134 (3)0.2891 (2)0.0223 (11)
C30.1561 (6)0.3987 (3)0.2116 (2)0.0213 (10)
H30.12030.34340.19150.026*
C40.2296 (6)0.4667 (3)0.1626 (2)0.0190 (10)
C50.2868 (6)0.5456 (3)0.1942 (2)0.0209 (10)
H50.33900.59150.16240.025*
C60.2681 (6)0.5576 (3)0.2718 (2)0.0196 (10)
C70.2418 (6)0.4468 (3)0.0817 (2)0.0203 (10)
H70.24160.38490.06950.024*
C80.2534 (6)0.5023 (3)0.0219 (2)0.0174 (10)
C90.2528 (6)0.4578 (3)0.0543 (2)0.0219 (10)
C100.2709 (6)0.5150 (3)0.1238 (2)0.0196 (10)
C110.2874 (6)0.6152 (3)0.1154 (2)0.0214 (10)
H11A0.41470.63140.11680.026*
H11B0.23750.64510.15850.026*
C120.1907 (6)0.6488 (3)0.0415 (2)0.0222 (11)
H12A0.06180.63670.04150.027*
H12B0.20700.71430.03750.027*
C130.2619 (6)0.6028 (3)0.0258 (2)0.0209 (10)
H13A0.19270.62320.07260.025*
H13B0.38700.62110.02870.025*
C140.2704 (6)0.4718 (3)0.1901 (2)0.0213 (10)
H140.25170.40900.18590.026*
C150.2938 (6)0.5054 (3)0.2679 (2)0.0189 (10)
C160.2337 (6)0.4519 (3)0.3252 (2)0.0214 (10)
H160.17810.39620.31230.026*
C170.2540 (6)0.4787 (3)0.4005 (2)0.0212 (10)
C180.3355 (6)0.5595 (3)0.4206 (2)0.0230 (11)
C190.4016 (6)0.6104 (3)0.3643 (2)0.0205 (10)
C200.3827 (6)0.5844 (3)0.2892 (2)0.0207 (10)
H200.43040.62060.25200.025*
C210.0191 (6)0.2687 (3)0.3221 (3)0.0253 (11)
H21A0.12390.23950.29650.038*
H21B0.02190.23470.36760.038*
H21C0.07570.27100.28800.038*
C220.1460 (7)0.3418 (3)0.4464 (3)0.0317 (13)
H22A0.03960.34050.41050.048*
H22B0.11940.31400.49400.048*
H22C0.24200.30860.42520.048*
O10.1786 (5)0.5049 (2)0.39617 (16)0.0311 (8)
H10.14170.45730.41740.047*
O20.0631 (5)0.3551 (2)0.34238 (17)0.0318 (8)
O30.2381 (5)0.3768 (2)0.05909 (16)0.0324 (9)
O40.1989 (5)0.4304 (2)0.45967 (17)0.0320 (8)
O50.3565 (5)0.5901 (2)0.49255 (16)0.0345 (9)
H5A0.30620.55500.52080.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0472 (4)0.0255 (3)0.0249 (3)0.0022 (2)0.0072 (2)0.0048 (2)
Br20.0337 (3)0.0243 (3)0.0237 (3)0.0030 (2)0.0007 (2)0.0040 (2)
C10.019 (2)0.030 (3)0.014 (2)0.008 (2)0.0015 (18)0.003 (2)
C20.019 (3)0.026 (3)0.023 (2)0.002 (2)0.003 (2)0.008 (2)
C30.020 (2)0.023 (3)0.021 (2)0.003 (2)0.0027 (19)0.004 (2)
C40.016 (2)0.026 (3)0.015 (2)0.006 (2)0.0057 (18)0.0016 (19)
C50.024 (3)0.026 (3)0.012 (2)0.003 (2)0.0013 (18)0.0012 (19)
C60.024 (3)0.015 (2)0.021 (2)0.0020 (19)0.0035 (19)0.0045 (19)
C70.022 (3)0.020 (2)0.019 (2)0.001 (2)0.0006 (19)0.003 (2)
C80.017 (2)0.019 (2)0.016 (2)0.0032 (19)0.0024 (18)0.0001 (19)
C90.026 (3)0.020 (3)0.019 (2)0.004 (2)0.002 (2)0.003 (2)
C100.024 (3)0.019 (2)0.016 (2)0.001 (2)0.0020 (19)0.0012 (19)
C110.030 (3)0.020 (2)0.014 (2)0.002 (2)0.0021 (19)0.0030 (19)
C120.032 (3)0.013 (2)0.022 (2)0.004 (2)0.001 (2)0.0020 (19)
C130.026 (3)0.020 (2)0.016 (2)0.000 (2)0.0001 (19)0.002 (2)
C140.026 (3)0.019 (2)0.018 (2)0.001 (2)0.001 (2)0.0001 (19)
C150.024 (3)0.020 (2)0.012 (2)0.004 (2)0.0005 (18)0.0012 (19)
C160.023 (3)0.019 (2)0.023 (2)0.001 (2)0.002 (2)0.002 (2)
C170.016 (2)0.026 (3)0.020 (2)0.002 (2)0.0009 (19)0.005 (2)
C180.025 (3)0.031 (3)0.014 (2)0.006 (2)0.0031 (19)0.003 (2)
C190.019 (2)0.023 (3)0.019 (2)0.005 (2)0.0009 (19)0.001 (2)
C200.021 (3)0.025 (3)0.017 (2)0.001 (2)0.0029 (19)0.001 (2)
C210.027 (3)0.017 (3)0.033 (3)0.009 (2)0.005 (2)0.014 (2)
C220.045 (3)0.034 (3)0.015 (2)0.011 (3)0.003 (2)0.010 (2)
O10.041 (2)0.036 (2)0.0162 (16)0.0011 (18)0.0039 (15)0.0011 (15)
O20.043 (2)0.030 (2)0.0216 (17)0.0027 (16)0.0006 (16)0.0059 (15)
O30.064 (3)0.0154 (18)0.0175 (16)0.0019 (17)0.0005 (16)0.0017 (14)
O40.043 (2)0.034 (2)0.0186 (17)0.0100 (17)0.0035 (15)0.0032 (15)
O50.053 (2)0.036 (2)0.0152 (17)0.0095 (18)0.0047 (16)0.0047 (15)
Geometric parameters (Å, º) top
Br1—C61.896 (4)C12—H12B0.9900
Br2—C191.899 (5)C13—H13A0.9900
C1—C61.369 (6)C13—H13B0.9900
C1—O11.369 (5)C14—C151.465 (6)
C1—C21.390 (6)C14—H140.9500
C2—O21.365 (5)C15—C201.393 (6)
C2—C31.390 (6)C15—C161.401 (6)
C3—C41.417 (6)C16—C171.392 (6)
C3—H30.9500C16—H160.9500
C4—C51.391 (6)C17—O41.370 (5)
C4—C71.462 (6)C17—C181.387 (6)
C5—C61.385 (6)C18—O51.353 (5)
C5—H50.9500C18—C191.385 (6)
C7—C81.344 (6)C19—C201.385 (6)
C7—H70.9500C20—H200.9500
C8—C131.505 (6)C21—O21.388 (5)
C8—C91.508 (6)C21—H21A0.9800
C9—O31.219 (5)C21—H21B0.9800
C9—C101.498 (6)C21—H21C0.9800
C10—C141.343 (6)C22—O41.397 (5)
C10—C111.511 (6)C22—H22A0.9800
C11—C121.527 (6)C22—H22B0.9800
C11—H11A0.9900C22—H22C0.9800
C11—H11B0.9900O1—H10.8400
C12—C131.520 (6)O5—H5A0.8400
C12—H12A0.9900
C6—C1—O1121.1 (4)C8—C13—H13A108.9
C6—C1—C2119.2 (4)C12—C13—H13A108.9
O1—C1—C2119.6 (4)C8—C13—H13B108.9
O2—C2—C3125.9 (4)C12—C13—H13B108.9
O2—C2—C1113.5 (4)H13A—C13—H13B107.7
C3—C2—C1120.6 (4)C10—C14—C15130.8 (4)
C2—C3—C4119.8 (4)C10—C14—H14114.6
C2—C3—H3120.1C15—C14—H14114.6
C4—C3—H3120.1C20—C15—C16117.8 (4)
C5—C4—C3118.6 (4)C20—C15—C14124.1 (4)
C5—C4—C7125.1 (4)C16—C15—C14118.0 (4)
C3—C4—C7116.4 (4)C17—C16—C15121.3 (4)
C6—C5—C4120.3 (4)C17—C16—H16119.4
C6—C5—H5119.9C15—C16—H16119.4
C4—C5—H5119.9O4—C17—C18114.8 (4)
C1—C6—C5121.5 (4)O4—C17—C16124.8 (4)
C1—C6—Br1118.7 (3)C18—C17—C16120.4 (4)
C5—C6—Br1119.8 (3)O5—C18—C19118.5 (4)
C8—C7—C4130.2 (4)O5—C18—C17123.3 (4)
C8—C7—H7114.9C19—C18—C17118.3 (4)
C4—C7—H7114.9C18—C19—C20121.9 (4)
C7—C8—C13125.4 (4)C18—C19—Br2119.3 (3)
C7—C8—C9115.6 (4)C20—C19—Br2118.8 (3)
C13—C8—C9119.0 (4)C19—C20—C15120.3 (4)
O3—C9—C10120.7 (4)C19—C20—H20119.8
O3—C9—C8120.6 (4)C15—C20—H20119.8
C10—C9—C8118.7 (4)O2—C21—H21A109.5
C14—C10—C9116.2 (4)O2—C21—H21B109.5
C14—C10—C11124.7 (4)H21A—C21—H21B109.5
C9—C10—C11119.1 (4)O2—C21—H21C109.5
C10—C11—C12111.9 (3)H21A—C21—H21C109.5
C10—C11—H11A109.2H21B—C21—H21C109.5
C12—C11—H11A109.2O4—C22—H22A109.5
C10—C11—H11B109.2O4—C22—H22B109.5
C12—C11—H11B109.2H22A—C22—H22B109.5
H11A—C11—H11B107.9O4—C22—H22C109.5
C13—C12—C11110.5 (4)H22A—C22—H22C109.5
C13—C12—H12A109.5H22B—C22—H22C109.5
C11—C12—H12A109.5C1—O1—H1109.5
C13—C12—H12B109.5C2—O2—C21120.3 (4)
C11—C12—H12B109.5C17—O4—C22118.1 (4)
H12A—C12—H12B108.1C18—O5—H5A109.5
C8—C13—C12113.3 (4)
C6—C1—C2—O2179.2 (4)C9—C10—C11—C1229.9 (6)
O1—C1—C2—O22.1 (6)C10—C11—C12—C1357.8 (5)
C6—C1—C2—C30.8 (7)C7—C8—C13—C12153.4 (4)
O1—C1—C2—C3177.9 (4)C9—C8—C13—C1224.9 (6)
O2—C2—C3—C4177.8 (4)C11—C12—C13—C855.5 (5)
C1—C2—C3—C42.1 (7)C9—C10—C14—C15176.6 (5)
C2—C3—C4—C52.4 (6)C11—C10—C14—C153.7 (8)
C2—C3—C4—C7178.6 (4)C10—C14—C15—C2023.8 (8)
C3—C4—C5—C61.4 (7)C10—C14—C15—C16160.6 (5)
C7—C4—C5—C6179.8 (4)C20—C15—C16—C173.1 (7)
O1—C1—C6—C5178.9 (4)C14—C15—C16—C17179.0 (4)
C2—C1—C6—C50.3 (7)C15—C16—C17—O4180.0 (4)
O1—C1—C6—Br11.4 (6)C15—C16—C17—C180.3 (7)
C2—C1—C6—Br1179.9 (3)O4—C17—C18—O51.5 (7)
C4—C5—C6—C10.1 (7)C16—C17—C18—O5178.8 (4)
C4—C5—C6—Br1179.6 (3)O4—C17—C18—C19177.3 (4)
C5—C4—C7—C823.3 (8)C16—C17—C18—C192.4 (7)
C3—C4—C7—C8157.9 (5)O5—C18—C19—C20178.8 (4)
C4—C7—C8—C132.0 (8)C17—C18—C19—C202.3 (7)
C4—C7—C8—C9176.4 (5)O5—C18—C19—Br22.4 (6)
C7—C8—C9—O31.7 (7)C17—C18—C19—Br2176.4 (3)
C13—C8—C9—O3176.8 (4)C18—C19—C20—C150.6 (7)
C7—C8—C9—C10178.1 (4)Br2—C19—C20—C15179.3 (3)
C13—C8—C9—C103.3 (6)C16—C15—C20—C193.2 (6)
O3—C9—C10—C140.2 (7)C14—C15—C20—C19178.8 (4)
C8—C9—C10—C14179.7 (4)C3—C2—O2—C217.8 (7)
O3—C9—C10—C11179.6 (4)C1—C2—O2—C21172.3 (4)
C8—C9—C10—C110.6 (6)C18—C17—O4—C22168.4 (4)
C14—C10—C11—C12149.8 (5)C16—C17—O4—C2211.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.842.152.613 (5)115
O5—H5A···O1i0.841.982.796 (5)163
O1—H1···O4ii0.842.302.809 (4)120
O5—H5A···O40.842.272.706 (5)113
Symmetry codes: (i) x, y, z+1; (ii) x, y, z1.

Experimental details

Crystal data
Chemical formulaC22H20Br2O5
Mr524.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)7.5550 (11), 14.938 (2), 17.763 (3)
β (°) 95.201 (3)
V3)1996.4 (5)
Z4
Radiation typeMo Kα
µ (mm1)4.09
Crystal size (mm)0.32 × 0.12 × 0.10
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.354, 0.685
No. of measured, independent and
observed [I > 2σ(I)] reflections
10131, 4349, 2760
Rint0.052
(sin θ/λ)max1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.110, 1.02
No. of reflections4349
No. of parameters266
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.78, 0.54

Computer programs: SMART (Bruker, 1999), SAINT-Plus (Bruker, 1999), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.842.152.613 (5)114.9
O5—H5A···O1i0.841.982.796 (5)163.3
O1—H1···O4ii0.842.302.809 (4)119.5
O5—H5A···O40.842.272.706 (5)112.8
Symmetry codes: (i) x, y, z+1; (ii) x, y, z1.
 

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