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Mol­ecules of the title compound, C18H14O4, crystallize as the enol tautomer, containing an intra­molecular O—H...O hydrogen bond. The entire mol­ecule is approximately planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053025/bi2113sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053025/bi2113Isup2.hkl
Contains datablock I

CCDC reference: 633622

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.056
  • wR factor = 0.138
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

1-(2-Furyl)-3-hydroxy-3-(2-methoxy-2-naphthyl)prop-2-en-1-one top
Crystal data top
C18H14O4F(000) = 616
Mr = 294.29Dx = 1.369 Mg m3
Monoclinic, P21/cMelting point: 414 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 3.9333 (7) ÅCell parameters from 3073 reflections
b = 10.986 (2) Åθ = 2.5–28.2°
c = 33.046 (6) ŵ = 0.10 mm1
β = 90.956 (3)°T = 298 K
V = 1427.8 (4) Å3Plate, yellow
Z = 40.30 × 0.20 × 0.06 mm
Data collection top
Bruker SMART CCD
diffractometer
3064 independent reflections
Radiation source: fine-focus sealed tube2599 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 45
Tmin = 0.972, Tmax = 0.989k = 1214
8120 measured reflectionsl = 4237
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0571P)2 + 0.3755P]
where P = (Fo2 + 2Fc2)/3
3064 reflections(Δ/σ)max = 0.010
203 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.25 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
C10.1024 (5)0.8204 (2)0.07103 (6)0.0639 (5)
H1A0.32000.82650.08360.096*
H1B0.13190.82430.04220.096*
H1C0.04000.88640.08000.096*
C20.1202 (4)0.68768 (16)0.12223 (5)0.0449 (4)
C30.2824 (4)0.57585 (16)0.13100 (5)0.0505 (4)
H30.33510.52300.11000.061*
C40.3620 (4)0.54479 (15)0.16959 (5)0.0466 (4)
H40.46900.47080.17480.056*
C50.2845 (4)0.62343 (14)0.20230 (5)0.0381 (4)
C60.1204 (4)0.73537 (14)0.19331 (5)0.0377 (4)
C70.0410 (4)0.76652 (15)0.15269 (5)0.0423 (4)
H70.06470.84030.14670.051*
C80.0372 (4)0.81324 (14)0.22593 (5)0.0411 (4)
H80.07030.88710.22060.049*
C90.1118 (4)0.78177 (14)0.26490 (5)0.0403 (4)
H90.05110.83370.28580.048*
C100.2809 (4)0.67091 (14)0.27409 (5)0.0374 (3)
C110.3654 (4)0.59430 (14)0.24279 (5)0.0393 (4)
H110.47840.52180.24860.047*
C120.3712 (4)0.63633 (14)0.31594 (5)0.0404 (4)
C130.3062 (4)0.70662 (15)0.34963 (5)0.0436 (4)
H130.19550.78100.34670.052*
C140.4078 (4)0.66573 (16)0.38859 (5)0.0461 (4)
C150.3530 (4)0.74153 (16)0.42410 (5)0.0476 (4)
C160.4249 (5)0.7246 (2)0.46355 (6)0.0625 (5)
H160.52120.65550.47520.075*
C170.3273 (5)0.8313 (2)0.48400 (6)0.0678 (6)
H170.34620.84620.51160.081*
C180.2027 (5)0.9065 (2)0.45581 (6)0.0651 (5)
H180.12050.98430.46090.078*
O10.0532 (3)0.70755 (12)0.08189 (4)0.0590 (4)
O20.5271 (3)0.53100 (11)0.31994 (4)0.0576 (4)
H20.565 (6)0.525 (2)0.3494 (7)0.086*
O30.5542 (4)0.56387 (12)0.39448 (4)0.0624 (4)
O40.2119 (3)0.85424 (12)0.41856 (4)0.0589 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0690 (13)0.0736 (14)0.0486 (11)0.0001 (10)0.0129 (9)0.0004 (10)
C20.0434 (9)0.0508 (10)0.0405 (9)0.0068 (7)0.0023 (7)0.0054 (7)
C30.0531 (10)0.0503 (10)0.0483 (10)0.0011 (8)0.0073 (7)0.0153 (8)
C40.0476 (9)0.0391 (9)0.0534 (10)0.0038 (7)0.0053 (7)0.0077 (7)
C50.0340 (7)0.0343 (8)0.0460 (9)0.0047 (6)0.0050 (6)0.0030 (6)
C60.0349 (7)0.0356 (8)0.0427 (8)0.0056 (6)0.0035 (6)0.0028 (6)
C70.0429 (8)0.0400 (9)0.0440 (9)0.0004 (7)0.0008 (7)0.0017 (7)
C80.0451 (9)0.0331 (8)0.0453 (9)0.0047 (6)0.0017 (7)0.0010 (6)
C90.0442 (8)0.0356 (8)0.0413 (8)0.0007 (6)0.0040 (6)0.0052 (6)
C100.0347 (7)0.0346 (8)0.0429 (8)0.0054 (6)0.0022 (6)0.0006 (6)
C110.0366 (8)0.0306 (8)0.0508 (9)0.0008 (6)0.0030 (6)0.0009 (6)
C120.0387 (8)0.0351 (8)0.0474 (9)0.0032 (6)0.0005 (6)0.0016 (7)
C130.0482 (9)0.0394 (9)0.0431 (9)0.0004 (7)0.0017 (7)0.0038 (7)
C140.0459 (9)0.0454 (9)0.0469 (9)0.0044 (7)0.0015 (7)0.0042 (7)
C150.0488 (9)0.0489 (10)0.0451 (9)0.0037 (8)0.0006 (7)0.0058 (7)
C160.0743 (13)0.0672 (13)0.0455 (10)0.0029 (10)0.0089 (9)0.0059 (9)
C170.0765 (14)0.0845 (15)0.0422 (10)0.0017 (12)0.0001 (9)0.0072 (10)
C180.0773 (13)0.0652 (13)0.0531 (11)0.0033 (11)0.0106 (9)0.0096 (10)
O10.0732 (9)0.0634 (8)0.0405 (7)0.0021 (7)0.0025 (6)0.0076 (6)
O20.0776 (9)0.0429 (7)0.0520 (8)0.0140 (6)0.0110 (6)0.0019 (6)
O30.0825 (9)0.0506 (8)0.0539 (8)0.0137 (7)0.0104 (6)0.0057 (6)
O40.0760 (9)0.0566 (8)0.0441 (7)0.0094 (7)0.0045 (6)0.0023 (6)
Geometric parameters (Å, º) top
C1—O11.426 (2)C9—H90.930
C1—H1A0.960C10—C111.379 (2)
C1—H1B0.960C10—C121.472 (2)
C1—H1C0.960C11—H110.930
C2—C71.368 (2)C12—O21.3152 (19)
C2—O11.372 (2)C12—C131.382 (2)
C2—C31.412 (2)C13—C141.415 (2)
C3—C41.352 (2)C13—H130.930
C3—H30.930C14—O31.272 (2)
C4—C51.421 (2)C14—C151.458 (2)
C4—H40.930C15—C161.342 (2)
C5—C111.407 (2)C15—O41.368 (2)
C5—C61.418 (2)C16—C171.409 (3)
C6—C71.415 (2)C16—H160.930
C6—C81.419 (2)C17—C181.333 (3)
C7—H70.930C17—H170.930
C8—C91.360 (2)C18—O41.359 (2)
C8—H80.930C18—H180.930
C9—C101.418 (2)O2—H20.98 (2)
O1—C1—H1A109.5C11—C10—C9118.79 (14)
O1—C1—H1B109.5C11—C10—C12119.34 (14)
H1A—C1—H1B109.5C9—C10—C12121.86 (14)
O1—C1—H1C109.5C10—C11—C5121.41 (14)
H1A—C1—H1C109.5C10—C11—H11119.3
H1B—C1—H1C109.5C5—C11—H11119.3
C7—C2—O1124.89 (16)O2—C12—C13120.17 (15)
C7—C2—C3120.48 (16)O2—C12—C10115.24 (14)
O1—C2—C3114.63 (15)C13—C12—C10124.58 (14)
C4—C3—C2120.67 (15)C12—C13—C14120.16 (15)
C4—C3—H3119.7C12—C13—H13119.9
C2—C3—H3119.7C14—C13—H13119.9
C3—C4—C5120.99 (16)O3—C14—C13122.60 (16)
C3—C4—H4119.5O3—C14—C15116.86 (15)
C5—C4—H4119.5C13—C14—C15120.53 (16)
C11—C5—C6119.43 (14)C16—C15—O4109.48 (17)
C11—C5—C4122.49 (15)C16—C15—C14132.17 (18)
C6—C5—C4118.08 (14)O4—C15—C14118.32 (14)
C7—C6—C5120.06 (14)C15—C16—C17107.23 (18)
C7—C6—C8121.66 (14)C15—C16—H16126.4
C5—C6—C8118.28 (14)C17—C16—H16126.4
C2—C7—C6119.71 (15)C18—C17—C16106.29 (18)
C2—C7—H7120.1C18—C17—H17126.9
C6—C7—H7120.1C16—C17—H17126.9
C9—C8—C6121.13 (14)C17—C18—O4110.84 (19)
C9—C8—H8119.4C17—C18—H18124.6
C6—C8—H8119.4O4—C18—H18124.6
C8—C9—C10120.93 (14)C2—O1—C1117.23 (14)
C8—C9—H9119.5C12—O2—H2102.6 (14)
C10—C9—H9119.5C18—O4—C15106.16 (15)
C7—C2—C3—C40.0 (3)C11—C10—C12—O20.7 (2)
O1—C2—C3—C4179.80 (15)C9—C10—C12—O2179.97 (14)
C2—C3—C4—C50.1 (3)C11—C10—C12—C13178.61 (15)
C3—C4—C5—C11179.61 (15)C9—C10—C12—C130.7 (2)
C3—C4—C5—C60.2 (2)O2—C12—C13—C140.1 (2)
C11—C5—C6—C7179.27 (13)C10—C12—C13—C14179.15 (14)
C4—C5—C6—C70.5 (2)C12—C13—C14—O31.3 (3)
C11—C5—C6—C81.3 (2)C12—C13—C14—C15177.44 (15)
C4—C5—C6—C8178.91 (14)O3—C14—C15—C160.9 (3)
O1—C2—C7—C6179.44 (14)C13—C14—C15—C16179.78 (19)
C3—C2—C7—C60.4 (2)O3—C14—C15—O4176.72 (15)
C5—C6—C7—C20.6 (2)C13—C14—C15—O42.1 (2)
C8—C6—C7—C2178.78 (14)O4—C15—C16—C170.3 (2)
C7—C6—C8—C9179.34 (14)C14—C15—C16—C17177.48 (19)
C5—C6—C8—C90.1 (2)C15—C16—C17—C180.1 (2)
C6—C8—C9—C101.1 (2)C16—C17—C18—O40.5 (3)
C8—C9—C10—C110.8 (2)C7—C2—O1—C11.8 (2)
C8—C9—C10—C12178.56 (14)C3—C2—O1—C1178.39 (15)
C9—C10—C11—C50.6 (2)C17—C18—O4—C150.7 (2)
C12—C10—C11—C5179.99 (13)C16—C15—O4—C180.6 (2)
C6—C5—C11—C101.7 (2)C14—C15—O4—C18177.55 (16)
C4—C5—C11—C10178.55 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.98 (2)1.55 (2)2.4899 (18)158 (2)
 

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