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The title compound, C20H16O3, was synthesized from 3-hydr­oxy-4-methoxy­benzaldehyde and 2-(prop-1-en-2-yl)naph­thalene in aqueous ethanol. The naphthalene ring system makes a dihedral angle of 15.8 (4) Å with the plane of the benzene ring. In the crystal structure, mol­ecules are linked into centrosymmetric dimers by O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048859/sj2169sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048859/sj2169Isup2.hkl
Contains datablock I

CCDC reference: 630482

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.056
  • wR factor = 0.144
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005).

(E)-3-(3-Hydroxy-4-methoxyphenyl)-1-(2-naphthyl)prop-2-en-1-one top
Crystal data top
C20H16O3Dx = 1.360 Mg m3
Mr = 304.33Melting point = 442–443 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ac 2abCell parameters from 5205 reflections
a = 14.7417 (11) Åθ = 1.2–27.8°
b = 6.1208 (4) ŵ = 0.09 mm1
c = 32.941 (3) ÅT = 293 K
V = 2972.3 (4) Å3Prism, colorless
Z = 80.22 × 0.16 × 0.14 mm
F(000) = 1280
Data collection top
Rigaku Saturn-70
diffractometer
3509 independent reflections
Radiation source: rotating anode3105 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.058
Detector resolution: 7.31 pixels mm-1θmax = 27.8°, θmin = 1.2°
ω scansh = 1819
Absorption correction: multi-scan
(Jacobson, 1998)
k = 87
Tmin = 0.980, Tmax = 0.987l = 4243
25516 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144 w = 1/[σ2(Fo2) + (0.0656P)2 + 0.9426P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max = 0.001
3509 reflectionsΔρmax = 0.24 e Å3
215 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0075 (13)
Special details top

Experimental. 1H NMR (CDCl3): δ 8.53 (s, 1H), 8.11 (d, 1H), 8.09–7.93 (m, 3H), 7.90 (d, 1H), 7.61–7.55 (m, 3H), 7.36 (s, 1H), 7.18 (d, 1H), 6.89 (d, 1H), 5.76 (s, 1H), 3.94 (s, 3H).

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
O30.09127 (10)0.5675 (2)0.40742 (4)0.0382 (3)
O10.02783 (9)0.1139 (2)0.60903 (3)0.0317 (3)
O20.11988 (9)0.2472 (2)0.61062 (4)0.0331 (3)
C10.06980 (11)0.0551 (3)0.57363 (5)0.0252 (4)
C20.11872 (11)0.1418 (3)0.57394 (5)0.0262 (4)
C30.16179 (12)0.2137 (3)0.53859 (5)0.0284 (4)
H30.19330.34530.53860.034*
C40.15766 (11)0.0889 (3)0.50323 (5)0.0279 (4)
H40.18540.13940.47970.033*
C50.11206 (11)0.1119 (3)0.50287 (5)0.0252 (4)
C60.06853 (11)0.1803 (3)0.53875 (5)0.0256 (4)
H60.03810.31340.53900.031*
C70.17932 (13)0.4303 (3)0.61467 (6)0.0349 (4)
H7A0.17860.48070.64230.052*
H7B0.23990.38760.60740.052*
H7C0.15950.54560.59700.052*
C80.10690 (11)0.2547 (3)0.46749 (5)0.0270 (4)
H80.08490.39460.47250.032*
C90.12943 (12)0.2127 (3)0.42870 (5)0.0278 (4)
H90.15520.07910.42170.033*
C100.11309 (11)0.3796 (3)0.39727 (5)0.0266 (4)
C110.12220 (10)0.3229 (3)0.35323 (5)0.0232 (3)
C120.09574 (10)0.4750 (3)0.32456 (5)0.0228 (3)
H120.07130.60730.33310.027*
C130.10488 (10)0.4342 (3)0.28232 (5)0.0211 (3)
C140.07786 (10)0.5896 (3)0.25245 (5)0.0225 (3)
H140.05260.72180.26050.027*
C150.08881 (11)0.5459 (3)0.21185 (5)0.0260 (4)
H150.07050.64800.19260.031*
C160.12782 (11)0.3466 (3)0.19925 (5)0.0278 (4)
H160.13520.31880.17170.033*
C170.15500 (11)0.1933 (3)0.22713 (5)0.0253 (4)
H170.18110.06330.21830.030*
C180.14347 (10)0.2320 (3)0.26949 (5)0.0213 (3)
C190.16910 (10)0.0762 (3)0.29935 (5)0.0242 (4)
H190.19340.05710.29130.029*
C200.15854 (11)0.1198 (3)0.34000 (5)0.0252 (4)
H200.17530.01530.35910.030*
H10.0129 (19)0.229 (4)0.6044 (7)0.066 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0558 (8)0.0351 (7)0.0239 (6)0.0164 (6)0.0002 (6)0.0034 (5)
O10.0381 (7)0.0362 (7)0.0208 (6)0.0085 (6)0.0041 (5)0.0005 (5)
O20.0411 (7)0.0312 (7)0.0268 (7)0.0065 (5)0.0039 (5)0.0065 (5)
C10.0248 (8)0.0297 (9)0.0212 (8)0.0005 (7)0.0010 (6)0.0037 (6)
C20.0277 (8)0.0275 (9)0.0235 (8)0.0017 (7)0.0025 (6)0.0020 (6)
C30.0290 (8)0.0265 (9)0.0298 (9)0.0023 (7)0.0010 (7)0.0014 (7)
C40.0283 (8)0.0315 (9)0.0238 (8)0.0018 (7)0.0018 (6)0.0032 (7)
C50.0236 (8)0.0302 (9)0.0218 (8)0.0001 (6)0.0026 (6)0.0015 (7)
C60.0266 (8)0.0274 (8)0.0227 (8)0.0037 (7)0.0029 (6)0.0020 (7)
C70.0468 (11)0.0240 (9)0.0338 (10)0.0050 (8)0.0011 (8)0.0054 (7)
C80.0251 (8)0.0317 (9)0.0243 (8)0.0037 (7)0.0006 (6)0.0012 (7)
C90.0291 (8)0.0311 (9)0.0234 (8)0.0039 (7)0.0011 (6)0.0006 (7)
C100.0261 (8)0.0305 (9)0.0231 (8)0.0042 (7)0.0004 (6)0.0028 (7)
C110.0208 (7)0.0266 (8)0.0223 (8)0.0024 (6)0.0003 (6)0.0014 (6)
C120.0216 (7)0.0234 (8)0.0233 (8)0.0015 (6)0.0001 (6)0.0034 (6)
C130.0176 (7)0.0239 (8)0.0219 (8)0.0011 (6)0.0001 (6)0.0018 (6)
C140.0213 (7)0.0221 (8)0.0241 (8)0.0011 (6)0.0001 (6)0.0017 (6)
C150.0250 (8)0.0290 (9)0.0239 (8)0.0013 (7)0.0000 (6)0.0027 (7)
C160.0288 (8)0.0351 (10)0.0196 (8)0.0032 (7)0.0034 (6)0.0039 (7)
C170.0246 (8)0.0266 (8)0.0245 (8)0.0008 (7)0.0013 (6)0.0056 (7)
C180.0177 (7)0.0242 (8)0.0220 (8)0.0005 (6)0.0002 (6)0.0022 (6)
C190.0221 (7)0.0237 (8)0.0267 (8)0.0023 (6)0.0007 (6)0.0028 (6)
C200.0239 (8)0.0262 (8)0.0256 (8)0.0035 (6)0.0015 (6)0.0013 (7)
Geometric parameters (Å, º) top
O3—C101.240 (2)C9—H90.9300
O1—C11.3682 (19)C10—C111.498 (2)
O1—H10.94 (3)C11—C121.382 (2)
O2—C21.370 (2)C11—C201.422 (2)
O2—C71.429 (2)C12—C131.420 (2)
C1—C61.381 (2)C12—H120.9300
C1—C21.405 (2)C13—C141.425 (2)
C2—C31.397 (2)C13—C181.427 (2)
C3—C41.394 (2)C14—C151.374 (2)
C3—H30.9300C14—H140.9300
C4—C51.401 (2)C15—C161.411 (2)
C4—H40.9300C15—H150.9300
C5—C61.409 (2)C16—C171.373 (2)
C5—C81.459 (2)C16—H160.9300
C6—H60.9300C17—C181.425 (2)
C7—H7A0.9600C17—H170.9300
C7—H7B0.9600C18—C191.421 (2)
C7—H7C0.9600C19—C201.374 (2)
C8—C91.345 (2)C19—H190.9300
C8—H80.9300C20—H200.9300
C9—C101.475 (2)
C1—O1—H1110.3 (15)O3—C10—C11119.96 (16)
C2—O2—C7117.33 (13)C9—C10—C11120.31 (15)
O1—C1—C6123.85 (15)C12—C11—C20119.06 (15)
O1—C1—C2116.85 (15)C12—C11—C10118.71 (15)
C6—C1—C2119.28 (15)C20—C11—C10122.22 (15)
O2—C2—C3125.52 (16)C11—C12—C13121.63 (15)
O2—C2—C1114.63 (14)C11—C12—H12119.2
C3—C2—C1119.84 (15)C13—C12—H12119.2
C4—C3—C2120.23 (16)C12—C13—C14122.20 (15)
C4—C3—H3119.9C12—C13—C18118.73 (14)
C2—C3—H3119.9C14—C13—C18119.07 (14)
C3—C4—C5120.59 (15)C15—C14—C13120.65 (15)
C3—C4—H4119.7C15—C14—H14119.7
C5—C4—H4119.7C13—C14—H14119.7
C4—C5—C6118.18 (15)C14—C15—C16120.16 (15)
C4—C5—C8123.89 (15)C14—C15—H15119.9
C6—C5—C8117.92 (15)C16—C15—H15119.9
C1—C6—C5121.80 (16)C17—C16—C15120.88 (15)
C1—C6—H6119.1C17—C16—H16119.6
C5—C6—H6119.1C15—C16—H16119.6
O2—C7—H7A109.5C16—C17—C18120.41 (15)
O2—C7—H7B109.5C16—C17—H17119.8
H7A—C7—H7B109.5C18—C17—H17119.8
O2—C7—H7C109.5C19—C18—C17122.30 (15)
H7A—C7—H7C109.5C19—C18—C13118.88 (14)
H7B—C7—H7C109.5C17—C18—C13118.82 (15)
C9—C8—C5129.14 (17)C20—C19—C18120.96 (15)
C9—C8—H8115.4C20—C19—H19119.5
C5—C8—H8115.4C18—C19—H19119.5
C8—C9—C10119.60 (16)C19—C20—C11120.71 (15)
C8—C9—H9120.2C19—C20—H20119.6
C10—C9—H9120.2C11—C20—H20119.6
O3—C10—C9119.73 (15)
C7—O2—C2—C38.6 (2)O3—C10—C11—C20171.43 (16)
C7—O2—C2—C1170.85 (15)C9—C10—C11—C208.9 (2)
O1—C1—C2—O21.8 (2)C20—C11—C12—C130.7 (2)
C6—C1—C2—O2176.46 (15)C10—C11—C12—C13178.23 (14)
O1—C1—C2—C3178.78 (15)C11—C12—C13—C14179.98 (14)
C6—C1—C2—C33.0 (2)C11—C12—C13—C180.8 (2)
O2—C2—C3—C4178.32 (16)C12—C13—C14—C15179.12 (15)
C1—C2—C3—C41.1 (3)C18—C13—C14—C150.1 (2)
C2—C3—C4—C51.4 (3)C13—C14—C15—C160.5 (2)
C3—C4—C5—C61.8 (2)C14—C15—C16—C170.3 (2)
C3—C4—C5—C8178.19 (16)C15—C16—C17—C180.6 (2)
O1—C1—C6—C5179.37 (15)C16—C17—C18—C19178.84 (15)
C2—C1—C6—C52.5 (2)C16—C17—C18—C131.2 (2)
C4—C5—C6—C10.1 (2)C12—C13—C18—C191.7 (2)
C8—C5—C6—C1179.84 (15)C14—C13—C18—C19179.09 (14)
C4—C5—C8—C911.8 (3)C12—C13—C18—C17178.30 (14)
C6—C5—C8—C9168.24 (17)C14—C13—C18—C170.9 (2)
C5—C8—C9—C10176.28 (16)C17—C18—C19—C20178.90 (15)
C8—C9—C10—O310.4 (3)C13—C18—C19—C201.1 (2)
C8—C9—C10—C11169.21 (15)C18—C19—C20—C110.4 (2)
O3—C10—C11—C127.5 (2)C12—C11—C20—C191.3 (2)
C9—C10—C11—C12172.18 (15)C10—C11—C20—C19177.55 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.94 (3)1.74 (3)2.6795 (18)176 (2)
Symmetry code: (i) x, y+1, z+1.
 

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