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The title compound, C18H20O5, was synthesized by the Reformatsky reaction in an aqueous medium. The benzene rings form a dihedral angle of 78.6 (1)°. Two inter­molecular O—H...O hydrogen bonds of 2.921 (2) Å between the hydroxyl and carbonyl groups form a centrosymmetric dimer. These hydrogen-bonded rings are stacked along the b axis, forming hydro­philic channels.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503610X/kp6066sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680503610X/kp6066Isup2.hkl
Contains datablock I

CCDC reference: 293936

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.120
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C12 .. 2.99 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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

3-Hydroxy-1-phenyl-3-(3,4,5-trimethoxylphenyl)propan-1-one top
Crystal data top
C18H20O5F(000) = 672
Mr = 316.34Dx = 1.322 Mg m3
Monoclinic, P21/nMelting point: 358 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 14.992 (3) ÅCell parameters from 1727 reflections
b = 5.0020 (11) Åθ = 2.7–25.9°
c = 21.237 (4) ŵ = 0.10 mm1
β = 93.375 (4)°T = 294 K
V = 1589.8 (6) Å3Needle, colourless
Z = 40.26 × 0.20 × 0.14 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3265 independent reflections
Radiation source: fine-focus sealed tube1938 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
φ and ω scansθmax = 26.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1812
Tmin = 0.977, Tmax = 0.987k = 66
8459 measured reflectionsl = 2026
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.1076P]
where P = (Fo2 + 2Fc2)/3
3265 reflections(Δ/σ)max = 0.001
215 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
O10.89749 (10)1.1562 (3)0.69499 (6)0.0527 (4)
O21.02445 (10)0.8148 (3)0.65892 (6)0.0493 (4)
O31.11897 (9)0.5149 (3)0.74280 (6)0.0475 (4)
O40.93658 (10)1.1006 (3)0.94216 (6)0.0394 (4)
H40.9881 (19)1.162 (6)0.9472 (12)0.096 (11)*
O50.89224 (9)0.6293 (3)1.03304 (6)0.0415 (4)
C10.96517 (12)0.8437 (4)0.84782 (8)0.0295 (4)
C20.92053 (13)1.0134 (4)0.80486 (8)0.0340 (5)
H20.87771.13170.81820.041*
C30.94027 (13)1.0055 (4)0.74181 (9)0.0353 (5)
C41.00698 (13)0.8353 (4)0.72183 (8)0.0353 (5)
C51.05275 (12)0.6701 (4)0.76550 (9)0.0331 (5)
C61.03056 (12)0.6724 (4)0.82816 (8)0.0328 (5)
H61.05980.55800.85710.039*
C70.83512 (15)1.3502 (5)0.71347 (10)0.0518 (6)
H7A0.78471.26210.73000.078*
H7B0.81551.45610.67760.078*
H7C0.86301.46380.74530.078*
C81.06784 (18)1.0378 (5)0.63273 (10)0.0640 (7)
H8A1.03351.19660.63900.096*
H8B1.07301.00950.58840.096*
H8C1.12631.05800.65310.096*
C91.16605 (15)0.3423 (5)0.78662 (11)0.0564 (7)
H9A1.19360.44650.82040.085*
H9B1.21120.24690.76560.085*
H9C1.12500.21730.80340.085*
C100.94156 (12)0.8384 (4)0.91651 (8)0.0306 (5)
H100.98800.73870.94090.037*
C110.85216 (13)0.7013 (4)0.92398 (8)0.0355 (5)
H11A0.80490.83110.91540.043*
H11B0.84480.56180.89240.043*
C120.84038 (12)0.5791 (4)0.98783 (9)0.0319 (5)
C130.76500 (12)0.3875 (4)0.99497 (8)0.0320 (5)
C140.76717 (14)0.2207 (4)1.04748 (9)0.0405 (5)
H140.81430.23411.07780.049*
C150.70049 (15)0.0362 (5)1.05507 (10)0.0488 (6)
H150.70250.07331.09050.059*
C160.63085 (14)0.0137 (5)1.01015 (11)0.0513 (6)
H160.58600.11151.01520.062*
C170.62755 (14)0.1757 (5)0.95788 (10)0.0507 (6)
H170.58040.16060.92760.061*
C180.69425 (13)0.3611 (4)0.95019 (9)0.0421 (5)
H180.69180.46970.91460.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0610 (10)0.0614 (11)0.0348 (8)0.0141 (9)0.0055 (7)0.0100 (7)
O20.0724 (11)0.0497 (10)0.0264 (8)0.0087 (8)0.0072 (7)0.0042 (7)
O30.0471 (9)0.0522 (10)0.0441 (8)0.0076 (8)0.0104 (7)0.0056 (8)
O40.0409 (9)0.0384 (9)0.0393 (8)0.0010 (7)0.0045 (7)0.0062 (7)
O50.0400 (8)0.0496 (10)0.0343 (8)0.0062 (7)0.0027 (7)0.0030 (7)
C10.0300 (10)0.0306 (11)0.0278 (10)0.0039 (9)0.0006 (8)0.0004 (9)
C20.0340 (11)0.0355 (12)0.0326 (11)0.0012 (9)0.0029 (9)0.0000 (9)
C30.0378 (11)0.0360 (12)0.0313 (11)0.0041 (10)0.0056 (9)0.0061 (9)
C40.0415 (12)0.0373 (12)0.0271 (11)0.0077 (10)0.0024 (9)0.0016 (9)
C50.0314 (10)0.0322 (11)0.0359 (11)0.0038 (9)0.0039 (9)0.0052 (9)
C60.0307 (10)0.0369 (12)0.0304 (11)0.0004 (9)0.0013 (8)0.0029 (9)
C70.0464 (13)0.0506 (15)0.0570 (14)0.0056 (12)0.0079 (11)0.0144 (12)
C80.0848 (19)0.0638 (18)0.0459 (14)0.0150 (15)0.0251 (13)0.0005 (13)
C90.0474 (13)0.0555 (16)0.0665 (16)0.0146 (12)0.0047 (12)0.0035 (13)
C100.0302 (10)0.0333 (12)0.0284 (10)0.0013 (9)0.0012 (8)0.0009 (9)
C110.0369 (11)0.0388 (12)0.0303 (11)0.0029 (10)0.0014 (9)0.0007 (9)
C120.0312 (11)0.0338 (12)0.0308 (11)0.0054 (9)0.0022 (9)0.0010 (9)
C130.0296 (10)0.0359 (12)0.0308 (11)0.0025 (9)0.0047 (8)0.0008 (9)
C140.0382 (12)0.0457 (14)0.0376 (12)0.0000 (10)0.0014 (9)0.0030 (10)
C150.0498 (14)0.0470 (15)0.0502 (14)0.0024 (12)0.0078 (11)0.0135 (11)
C160.0385 (13)0.0509 (15)0.0650 (16)0.0084 (11)0.0082 (12)0.0023 (13)
C170.0360 (12)0.0615 (16)0.0534 (14)0.0041 (12)0.0063 (10)0.0012 (12)
C180.0364 (11)0.0505 (14)0.0393 (12)0.0031 (11)0.0002 (10)0.0075 (10)
Geometric parameters (Å, º) top
O1—C31.376 (2)C8—H8B0.9600
O1—C71.419 (3)C8—H8C0.9600
O2—C41.380 (2)C9—H9A0.9600
O2—C81.421 (3)C9—H9B0.9600
O3—C51.370 (2)C9—H9C0.9600
O3—C91.425 (2)C10—C111.522 (3)
O4—C101.424 (2)C10—H100.9800
O4—H40.83 (3)C11—C121.507 (3)
O5—C121.225 (2)C11—H11A0.9700
C1—C61.385 (3)C11—H11B0.9700
C1—C21.389 (3)C12—C131.496 (3)
C1—C101.521 (2)C13—C181.389 (3)
C2—C31.389 (2)C13—C141.392 (3)
C2—H20.9300C14—C151.377 (3)
C3—C41.398 (3)C14—H140.9300
C4—C51.392 (3)C15—C161.377 (3)
C5—C61.391 (2)C15—H150.9300
C6—H60.9300C16—C171.373 (3)
C7—H7A0.9600C16—H160.9300
C7—H7B0.9600C17—C181.381 (3)
C7—H7C0.9600C17—H170.9300
C8—H8A0.9600C18—H180.9300
C3—O1—C7117.49 (15)O3—C9—H9C109.5
C4—O2—C8115.96 (16)H9A—C9—H9C109.5
C5—O3—C9117.05 (15)H9B—C9—H9C109.5
C10—O4—H4109 (2)O4—C10—C1111.80 (15)
C6—C1—C2120.17 (16)O4—C10—C11107.99 (16)
C6—C1—C10119.15 (16)C1—C10—C11111.33 (15)
C2—C1—C10120.67 (17)O4—C10—H10108.5
C1—C2—C3119.60 (18)C1—C10—H10108.5
C1—C2—H2120.2C11—C10—H10108.5
C3—C2—H2120.2C12—C11—C10115.28 (16)
O1—C3—C2124.35 (18)C12—C11—H11A108.5
O1—C3—C4115.19 (17)C10—C11—H11A108.5
C2—C3—C4120.46 (17)C12—C11—H11B108.5
O2—C4—C5119.11 (18)C10—C11—H11B108.5
O2—C4—C3121.26 (17)H11A—C11—H11B107.5
C5—C4—C3119.50 (17)O5—C12—C13119.99 (17)
O3—C5—C6124.07 (18)O5—C12—C11121.30 (17)
O3—C5—C4116.16 (17)C13—C12—C11118.69 (16)
C6—C5—C4119.76 (18)C18—C13—C14118.22 (19)
C1—C6—C5120.45 (18)C18—C13—C12122.86 (17)
C1—C6—H6119.8C14—C13—C12118.88 (17)
C5—C6—H6119.8C15—C14—C13120.8 (2)
O1—C7—H7A109.5C15—C14—H14119.6
O1—C7—H7B109.5C13—C14—H14119.6
H7A—C7—H7B109.5C16—C15—C14120.0 (2)
O1—C7—H7C109.5C16—C15—H15120.0
H7A—C7—H7C109.5C14—C15—H15120.0
H7B—C7—H7C109.5C17—C16—C15120.1 (2)
O2—C8—H8A109.5C17—C16—H16119.9
O2—C8—H8B109.5C15—C16—H16119.9
H8A—C8—H8B109.5C16—C17—C18120.0 (2)
O2—C8—H8C109.5C16—C17—H17120.0
H8A—C8—H8C109.5C18—C17—H17120.0
H8B—C8—H8C109.5C17—C18—C13120.81 (19)
O3—C9—H9A109.5C17—C18—H18119.6
O3—C9—H9B109.5C13—C18—H18119.6
H9A—C9—H9B109.5
C6—C1—C2—C31.6 (3)C4—C5—C6—C12.0 (3)
C10—C1—C2—C3176.92 (17)C6—C1—C10—O4133.53 (18)
C7—O1—C3—C26.2 (3)C2—C1—C10—O447.9 (2)
C7—O1—C3—C4174.24 (18)C6—C1—C10—C11105.6 (2)
C1—C2—C3—O1177.11 (18)C2—C1—C10—C1173.0 (2)
C1—C2—C3—C42.4 (3)O4—C10—C11—C1282.4 (2)
C8—O2—C4—C5112.0 (2)C1—C10—C11—C12154.55 (16)
C8—O2—C4—C372.3 (3)C10—C11—C12—O512.5 (3)
O1—C3—C4—O22.9 (3)C10—C11—C12—C13165.84 (17)
C2—C3—C4—O2176.70 (17)O5—C12—C13—C18166.97 (18)
O1—C3—C4—C5178.57 (17)C11—C12—C13—C1814.7 (3)
C2—C3—C4—C51.0 (3)O5—C12—C13—C1415.6 (3)
C9—O3—C5—C61.3 (3)C11—C12—C13—C14162.79 (18)
C9—O3—C5—C4179.38 (18)C18—C13—C14—C150.6 (3)
O2—C4—C5—O36.1 (3)C12—C13—C14—C15178.16 (18)
C3—C4—C5—O3178.11 (17)C13—C14—C15—C160.5 (3)
O2—C4—C5—C6174.58 (17)C14—C15—C16—C170.3 (3)
C3—C4—C5—C61.2 (3)C15—C16—C17—C180.2 (4)
C2—C1—C6—C50.6 (3)C16—C17—C18—C130.3 (3)
C10—C1—C6—C5179.15 (17)C14—C13—C18—C170.5 (3)
O3—C5—C6—C1177.26 (17)C12—C13—C18—C17177.99 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O5i0.83 (3)2.10 (3)2.921 (2)171 (3)
Symmetry code: (i) x+2, y+2, z+2.
 

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