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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1092–o1093.
Published online 2009 April 22. doi:  10.1107/S160053680901441X
PMCID: PMC2977771

(E)-3-[4-(Dec­yloxy)phen­yl]-1-(4-hydroxy­phen­yl)prop-2-en-1-one

Abstract

In the title compound, C25H32O3, the enone group adopts an scis conformation. The alk­oxy unit is nearly planar and is in a trans conformation. The two benzene rings make a dihedral angle of 18.87 (9)°. In the crystal structure, mol­ecules are linked into chains running along the a axis by inter­molecular O—H(...)O hydrogen bonds involving the hydr­oxy and keto groups. The chains are crosslinked along the b axis via C—H(...)O hydrogen bonds, forming a two-dimensional network parallel to the ab plane.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 [triangle]); Xue et al. (2004 [triangle]); Satyanarayana et al. (2004 [triangle]); Lee et al. (2006 [triangle]). For related structures, see: Ng et al. (2006 [triangle]); Razak et al. (2009 [triangle]); Ngaini, Fadzillah et al. (2009 [triangle]); Ngaini, Rahman et al. (2009 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1092-scheme1.jpg

Experimental

Crystal data

  • C25H32O3
  • M r = 380.51
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1092-efi1.jpg
  • a = 10.5192 (3) Å
  • b = 9.9839 (3) Å
  • c = 40.8415 (12) Å
  • V = 4289.3 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 K
  • 0.58 × 0.49 × 0.03 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.957, T max = 0.998
  • 42832 measured reflections
  • 4922 independent reflections
  • 3526 reflections with I > 2σ(I)
  • R int = 0.082

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.132
  • S = 1.10
  • 4922 reflections
  • 258 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901441X/ci2782sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901441X/ci2782Isup2.hkl

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

Acknowledgments

HKF and IAR thank the Malaysian government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312 and for Research University Golden Goose grant No. 1001/PFIZIK/811012. ZN and HH thank Universiti Malaysia Sarawak for Geran Penyelidikan Dana Khas Inovasi grant No. DI/01/2007(01). NIAR thanks the Malaysian government and Universiti Malaysia Sarawak for providing a scholarship for postgraduate studies.

supplementary crystallographic information

Comment

Chalcone derivatives possess a wide range of biological properties such as antimalarial (Xue et al., 2004), antiangiogenic and antitumour (Lee et al., 2006), anticancer (Bhat et al., 2005) and antihyperglycemic (Satyanarayana et al., 2004) activities. Chalcones have been widely studied and developed as one of the pharmaceutically important molecules. We have synthesized the title chalcone derivative and tested and confirmed its activities against E. coli ATCC 8739. As part of our studies on chalcone derivatives, we report here the crystal structure of the title compound.

In the title molecule (Fig 1), bond lengths show normal values (Allen et al., 1987). The mean plane through the enone moiety (O2/C7/C8/C9) form dihedral angles of 19.26 (12)° and 2.14 (12)°, respectively, with the C1-C6 and C10-C15 benzene rings. The dihedral angle between the two benzene rings is 18.87 (9)°. The conformation of the enone moiety is s-cis with O2—C7—C8—C9 torsion angle being 5.4 (3)°. Slight enlargement of C5—C6—C7 (122.43 (18)°) angle is as a result of the short H5···H8 (2.18 Å) contact whereas short H8···H11 (2.30 Å) contact widened the C8—C9—C10 (128.13 (19)°) and C9—C10—C11 (123.63 (18)°) angles. Similarly, strain induced by close interatomic contact between H14 and H16A (2.27 Å) resulted in the opening of O3—C13—C14 (124.86 (17)°) angle. Related structures by Ng et al.(2006), Razak et al. (2009), Ngaini, Fadzillah et al. (2009) and Ngaini, Rahman et al. (2009) have also reported similar features.

The zigzag alkoxyl tail adopts a trans conformation with the largest deviation from the ideal value being 175.44 (17)° for C17—C18—C19—C20 torsion angle. The alkoxyl chain (O3/C16-C25) is nearly planar with the maximum deviation from the least-squares plane being 0.116 (1) Å for atom C19. The dihedral angle between the O3/C16-C25 and C10-C15 planes is 6.29 (13)°.

In the crystal structure, the molecules are arranged in alternating head-to-head zigzag layers along the c axis (Fig. 2). Intermolecular O1—H1O1···O2(x + 1/2,y,-z + 1/2) hydrogen bonds (Table 1) between hydroxy and keto groups form extended chains along the a axis. These chains are interconnected along the b axis by C5—H5···O1(-x + 2,y - 1/2,-z + 1/2) intermolecular interactions forming a two-dimensional network parallel to the ab plane.

Experimental

A mixture of 4-hydroxyacetophenone (2.72 g, 20 mmol) and 4-decyloxybenzaldehyde (5.25 ml, 20 mmol) and KOH (4.04 g, 72 mmol) in methanol (60 ml) was heated at reflux for 24 h. The reaction mixture was cooled to room temperature and acidified with cold diluted HCl (2 N). The resulting precipitate was filtered, washed and dried. After redissolving in a hexane-ethanol (7:1) solution, followed by few days of slow evaporation, crystals were collected.

Refinement

The O-bound H atom was located in a difference Fourier map and refined freely. C-bound H atoms were positioned geometrically and refined using a riding model with C-H = 0.93–0.97 Å. The Uiso(H) values were constrained to be 1.5Ueq(Cmethyl) and 1.2Ueq(C). A rotating group model was used for the methyl group.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
The crystal packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds.

Crystal data

C25H32O3F(000) = 1648
Mr = 380.51Dx = 1.178 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4176 reflections
a = 10.5192 (3) Åθ = 2.2–23.9°
b = 9.9839 (3) ŵ = 0.08 mm1
c = 40.8415 (12) ÅT = 100 K
V = 4289.3 (2) Å3Plate, colourless
Z = 80.58 × 0.49 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer4922 independent reflections
Radiation source: sealed tube3526 reflections with I > 2σ(I)
graphiteRint = 0.082
π and ω scansθmax = 27.5°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −13→13
Tmin = 0.957, Tmax = 0.998k = −12→12
42832 measured reflectionsl = −53→52

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.10w = 1/[σ2(Fo2) + (0.0368P)2 + 2.6345P] where P = (Fo2 + 2Fc2)/3
4922 reflections(Δ/σ)max = 0.001
258 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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
O10.97999 (14)0.70636 (15)0.20018 (3)0.0232 (3)
O20.66825 (13)0.56794 (14)0.32684 (3)0.0228 (3)
O30.93786 (13)−0.03516 (14)0.45190 (3)0.0227 (3)
C10.79176 (18)0.6934 (2)0.27426 (5)0.0213 (4)
H10.72420.73970.28360.026*
C20.83983 (19)0.7353 (2)0.24449 (5)0.0220 (4)
H20.80510.80960.23400.026*
C30.94058 (19)0.6659 (2)0.23015 (5)0.0198 (4)
C40.9958 (2)0.5589 (2)0.24676 (5)0.0224 (4)
H41.06550.51490.23780.027*
C50.94723 (18)0.5179 (2)0.27665 (5)0.0219 (4)
H50.98470.44630.28750.026*
C60.84262 (18)0.5826 (2)0.29070 (4)0.0193 (4)
C70.77760 (18)0.5307 (2)0.32020 (4)0.0189 (4)
C80.84031 (19)0.4306 (2)0.34137 (4)0.0206 (4)
H80.92480.40780.33770.025*
C90.77621 (19)0.3725 (2)0.36590 (4)0.0204 (4)
H90.69320.40180.36900.024*
C100.82043 (18)0.2687 (2)0.38841 (4)0.0204 (4)
C110.94097 (18)0.2090 (2)0.38649 (5)0.0216 (4)
H110.99810.23780.37060.026*
C120.97590 (19)0.1086 (2)0.40773 (5)0.0222 (5)
H121.05600.06980.40590.027*
C130.89207 (19)0.0645 (2)0.43198 (4)0.0201 (4)
C140.77209 (18)0.1205 (2)0.43435 (5)0.0213 (4)
H140.71530.09140.45030.026*
C150.73770 (19)0.2212 (2)0.41247 (4)0.0223 (4)
H150.65670.25810.41390.027*
C160.85615 (19)−0.0838 (2)0.47766 (5)0.0223 (5)
H16A0.7759−0.11410.46860.027*
H16B0.8391−0.01300.49330.027*
C170.92412 (19)−0.1985 (2)0.49413 (5)0.0226 (5)
H17A1.0055−0.16740.50230.027*
H17B0.9403−0.26840.47820.027*
C180.84727 (19)−0.2561 (2)0.52231 (5)0.0241 (5)
H18A0.7647−0.28370.51420.029*
H18B0.8337−0.18670.53860.029*
C190.91156 (19)−0.3754 (2)0.53860 (5)0.0245 (5)
H19A0.9968−0.34960.54510.029*
H19B0.9190−0.44720.52270.029*
C200.84121 (19)−0.4277 (2)0.56855 (5)0.0246 (5)
H20A0.8313−0.35520.58420.030*
H20B0.7569−0.45650.56200.030*
C210.9087 (2)−0.5439 (2)0.58526 (5)0.0260 (5)
H21A0.9129−0.61870.57010.031*
H21B0.9951−0.51720.59030.031*
C220.8444 (2)−0.5903 (2)0.61656 (5)0.0282 (5)
H22A0.8427−0.51610.63190.034*
H22B0.7570−0.61360.61160.034*
C230.90728 (19)−0.7093 (2)0.63310 (5)0.0266 (5)
H23A0.9130−0.78230.61750.032*
H23B0.9932−0.68460.63930.032*
C240.8373 (2)−0.7579 (2)0.66318 (5)0.0347 (6)
H24A0.7505−0.77990.65720.042*
H24B0.8342−0.68610.67920.042*
C250.8993 (2)−0.8805 (3)0.67877 (6)0.0446 (7)
H25A0.8492−0.90950.69710.067*
H25B0.9833−0.85770.68610.067*
H25C0.9043−0.95130.66290.067*
H1O11.046 (3)0.654 (3)0.1909 (7)0.078 (10)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0271 (8)0.0216 (8)0.0209 (7)0.0019 (7)0.0033 (6)0.0032 (6)
O20.0224 (7)0.0248 (8)0.0213 (7)0.0034 (7)0.0014 (6)0.0005 (6)
O30.0228 (7)0.0231 (8)0.0222 (7)0.0004 (6)0.0017 (6)0.0052 (6)
C10.0207 (10)0.0187 (11)0.0245 (10)0.0008 (9)0.0005 (8)−0.0032 (9)
C20.0230 (10)0.0175 (11)0.0255 (11)0.0006 (9)0.0002 (8)0.0024 (9)
C30.0239 (10)0.0159 (11)0.0195 (10)−0.0047 (9)−0.0001 (8)0.0004 (8)
C40.0239 (10)0.0195 (11)0.0237 (10)0.0032 (9)0.0025 (8)−0.0016 (9)
C50.0235 (10)0.0186 (11)0.0236 (10)0.0005 (9)−0.0006 (8)0.0010 (9)
C60.0212 (10)0.0169 (11)0.0198 (10)−0.0021 (9)−0.0010 (8)−0.0018 (8)
C70.0226 (10)0.0152 (10)0.0190 (10)−0.0001 (9)−0.0018 (8)−0.0048 (8)
C80.0203 (10)0.0213 (11)0.0203 (10)0.0004 (9)−0.0006 (8)−0.0017 (8)
C90.0228 (10)0.0205 (11)0.0178 (10)−0.0004 (9)−0.0012 (8)−0.0029 (8)
C100.0231 (10)0.0208 (11)0.0171 (9)−0.0012 (9)−0.0002 (8)−0.0028 (8)
C110.0222 (10)0.0246 (12)0.0178 (10)−0.0032 (9)0.0008 (8)0.0019 (9)
C120.0187 (10)0.0265 (12)0.0215 (10)0.0000 (9)0.0002 (8)−0.0016 (9)
C130.0238 (10)0.0187 (11)0.0179 (9)−0.0012 (9)−0.0023 (8)0.0002 (8)
C140.0223 (10)0.0199 (11)0.0216 (10)−0.0029 (9)0.0038 (8)0.0011 (9)
C150.0213 (10)0.0235 (12)0.0221 (10)0.0021 (9)0.0005 (8)−0.0017 (9)
C160.0249 (10)0.0212 (11)0.0207 (10)−0.0017 (9)0.0021 (8)0.0030 (8)
C170.0224 (10)0.0209 (11)0.0245 (10)−0.0031 (9)−0.0022 (8)−0.0002 (9)
C180.0260 (10)0.0233 (12)0.0230 (10)−0.0006 (10)−0.0015 (8)0.0036 (9)
C190.0279 (11)0.0223 (12)0.0234 (10)0.0014 (10)0.0018 (9)0.0011 (9)
C200.0249 (11)0.0235 (12)0.0255 (11)−0.0018 (10)−0.0006 (9)0.0032 (9)
C210.0272 (11)0.0249 (12)0.0261 (11)0.0006 (10)0.0009 (9)0.0037 (9)
C220.0261 (11)0.0269 (12)0.0315 (12)0.0029 (10)0.0007 (9)0.0071 (10)
C230.0260 (11)0.0270 (12)0.0268 (11)0.0001 (10)0.0005 (9)0.0046 (9)
C240.0357 (13)0.0337 (14)0.0346 (12)0.0097 (12)0.0066 (10)0.0125 (10)
C250.0445 (15)0.0485 (17)0.0408 (14)0.0177 (13)0.0110 (12)0.0201 (13)

Geometric parameters (Å, °)

O1—C31.354 (2)C16—C171.508 (3)
O1—H1O10.94 (3)C16—H16A0.97
O2—C71.239 (2)C16—H16B0.97
O3—C131.373 (2)C17—C181.520 (3)
O3—C161.443 (2)C17—H17A0.97
C1—C21.382 (3)C17—H17B0.97
C1—C61.400 (3)C18—C191.522 (3)
C1—H10.93C18—H18A0.97
C2—C31.395 (3)C18—H18B0.97
C2—H20.93C19—C201.522 (3)
C3—C41.392 (3)C19—H19A0.97
C4—C51.385 (3)C19—H19B0.97
C4—H40.93C20—C211.522 (3)
C5—C61.399 (3)C20—H20A0.97
C5—H50.93C20—H20B0.97
C6—C71.479 (3)C21—C221.518 (3)
C7—C81.477 (3)C21—H21A0.97
C8—C91.340 (3)C21—H21B0.97
C8—H80.93C22—C231.518 (3)
C9—C101.461 (3)C22—H22A0.97
C9—H90.93C22—H22B0.97
C10—C151.396 (3)C23—C241.513 (3)
C10—C111.403 (3)C23—H23A0.97
C11—C121.376 (3)C23—H23B0.97
C11—H110.93C24—C251.526 (3)
C12—C131.397 (3)C24—H24A0.97
C12—H120.93C24—H24B0.97
C13—C141.384 (3)C25—H25A0.96
C14—C151.393 (3)C25—H25B0.96
C14—H140.93C25—H25C0.96
C15—H150.93
C3—O1—H1O1115.1 (18)C16—C17—H17A109.2
C13—O3—C16117.84 (15)C18—C17—H17A109.2
C2—C1—C6121.44 (19)C16—C17—H17B109.2
C2—C1—H1119.3C18—C17—H17B109.2
C6—C1—H1119.3H17A—C17—H17B107.9
C1—C2—C3119.77 (19)C17—C18—C19113.01 (17)
C1—C2—H2120.1C17—C18—H18A109.0
C3—C2—H2120.1C19—C18—H18A109.0
O1—C3—C4122.77 (18)C17—C18—H18B109.0
O1—C3—C2117.63 (18)C19—C18—H18B109.0
C4—C3—C2119.60 (18)H18A—C18—H18B107.8
C5—C4—C3120.12 (19)C18—C19—C20113.81 (17)
C5—C4—H4119.9C18—C19—H19A108.8
C3—C4—H4119.9C20—C19—H19A108.8
C4—C5—C6121.03 (19)C18—C19—H19B108.8
C4—C5—H5119.5C20—C19—H19B108.8
C6—C5—H5119.5H19A—C19—H19B107.7
C5—C6—C1117.92 (18)C21—C20—C19113.30 (17)
C5—C6—C7122.43 (18)C21—C20—H20A108.9
C1—C6—C7119.38 (17)C19—C20—H20A108.9
O2—C7—C8119.34 (17)C21—C20—H20B108.9
O2—C7—C6120.14 (18)C19—C20—H20B108.9
C8—C7—C6120.48 (17)H20A—C20—H20B107.7
C9—C8—C7120.40 (18)C22—C21—C20113.74 (17)
C9—C8—H8119.8C22—C21—H21A108.8
C7—C8—H8119.8C20—C21—H21A108.8
C8—C9—C10128.13 (19)C22—C21—H21B108.8
C8—C9—H9115.9C20—C21—H21B108.8
C10—C9—H9115.9H21A—C21—H21B107.7
C15—C10—C11117.26 (18)C23—C22—C21114.78 (17)
C15—C10—C9119.05 (18)C23—C22—H22A108.6
C11—C10—C9123.63 (18)C21—C22—H22A108.6
C12—C11—C10121.05 (18)C23—C22—H22B108.6
C12—C11—H11119.5C21—C22—H22B108.6
C10—C11—H11119.5H22A—C22—H22B107.5
C11—C12—C13120.53 (19)C24—C23—C22113.59 (18)
C11—C12—H12119.7C24—C23—H23A108.8
C13—C12—H12119.7C22—C23—H23A108.8
O3—C13—C14124.86 (17)C24—C23—H23B108.8
O3—C13—C12115.28 (17)C22—C23—H23B108.8
C14—C13—C12119.86 (18)H23A—C23—H23B107.7
C13—C14—C15118.92 (18)C23—C24—C25112.84 (19)
C13—C14—H14120.5C23—C24—H24A109.0
C15—C14—H14120.5C25—C24—H24A109.0
C14—C15—C10122.36 (19)C23—C24—H24B109.0
C14—C15—H15118.8C25—C24—H24B109.0
C10—C15—H15118.8H24A—C24—H24B107.8
O3—C16—C17107.35 (15)C24—C25—H25A109.5
O3—C16—H16A110.2C24—C25—H25B109.5
C17—C16—H16A110.2H25A—C25—H25B109.5
O3—C16—H16B110.2C24—C25—H25C109.5
C17—C16—H16B110.2H25A—C25—H25C109.5
H16A—C16—H16B108.5H25B—C25—H25C109.5
C16—C17—C18111.91 (17)
C6—C1—C2—C30.5 (3)C9—C10—C11—C12−177.86 (19)
C1—C2—C3—O1176.56 (18)C10—C11—C12—C13−0.6 (3)
C1—C2—C3—C4−3.1 (3)C16—O3—C13—C14−1.2 (3)
O1—C3—C4—C5−176.75 (18)C16—O3—C13—C12179.30 (17)
C2—C3—C4—C52.9 (3)C11—C12—C13—O3−179.39 (17)
C3—C4—C5—C6−0.1 (3)C11—C12—C13—C141.1 (3)
C4—C5—C6—C1−2.5 (3)O3—C13—C14—C15−179.93 (18)
C4—C5—C6—C7171.60 (18)C12—C13—C14—C15−0.5 (3)
C2—C1—C6—C52.3 (3)C13—C14—C15—C10−0.7 (3)
C2—C1—C6—C7−171.99 (18)C11—C10—C15—C141.2 (3)
C5—C6—C7—O2−160.79 (19)C9—C10—C15—C14178.62 (19)
C1—C6—C7—O213.2 (3)C13—O3—C16—C17175.86 (16)
C5—C6—C7—C817.0 (3)O3—C16—C17—C18178.90 (16)
C1—C6—C7—C8−168.94 (18)C16—C17—C18—C19177.92 (17)
O2—C7—C8—C95.4 (3)C17—C18—C19—C20175.44 (17)
C6—C7—C8—C9−172.41 (18)C18—C19—C20—C21−178.11 (18)
C7—C8—C9—C10177.52 (18)C19—C20—C21—C22175.79 (18)
C8—C9—C10—C15−179.9 (2)C20—C21—C22—C23177.99 (18)
C8—C9—C10—C11−2.7 (3)C21—C22—C23—C24−176.90 (19)
C15—C10—C11—C12−0.6 (3)C22—C23—C24—C25178.0 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O1···O2i0.95 (3)1.71 (3)2.655 (2)177 (3)
C5—H5···O1ii0.932.483.340 (2)155

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) −x+2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2782).

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