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In the title compound, C22H20O4, the naphthalene ring system makes a dihedral angle of 36.3 (5)° with the benzene ring. Neighboring mol­ecules are linked via weak C—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604815X/xu2159sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604815X/xu2159Isup2.hkl
Contains datablock I

CCDC reference: 630527

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.066
  • wR factor = 0.146
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

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, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

(E)-1-(naphthalen-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one top
Crystal data top
C22H20O4Dx = 1.307 Mg m3
Mr = 348.38Melting point: 392-393K K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ac 2abCell parameters from 5952 reflections
a = 13.5903 (13) Åθ = 1.4–27.1°
b = 8.6378 (9) ŵ = 0.09 mm1
c = 30.169 (3) ÅT = 113 K
V = 3541.5 (6) Å3Platelet, colorless
Z = 80.34 × 0.22 × 0.06 mm
F(000) = 1472
Data collection top
Rigaku Saturn-70
diffractometer
3229 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.073
Confocal monochromatorθmax = 26.0°, θmin = 1.3°
Detector resolution: 7.31 pixels mm-1h = 1616
ω scansk = 109
26883 measured reflectionsl = 3737
3477 independent 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)] = 0.066H-atom parameters constrained
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0553P)2 + 1.8606P]
where P = (Fo2 + 2Fc2)/3
S = 1.23(Δ/σ)max = 0.001
3477 reflectionsΔρmax = 0.22 e Å3
240 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0066 (9)
Special details top

Experimental. 1H NMR (CDCl3): 8.53 (d, 1H), 8.10(dd, 1H), 8.09 (dd, 1H), 7.99 (d, 1H), 7.95(d, 1H),7.90(d, 1H), 7.53–7.63 (m, 3H), 7.26(s, 2H), 3.94(s, 6H), 3.91(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
O10.38413 (12)0.02823 (17)0.93239 (5)0.0293 (4)
O20.19524 (11)0.21810 (17)0.70749 (5)0.0249 (4)
O30.04222 (11)0.40238 (17)0.72466 (5)0.0265 (4)
O40.02470 (11)0.44389 (18)0.80901 (5)0.0275 (4)
C10.31570 (16)0.3630 (2)0.99549 (7)0.0252 (5)
H10.25400.38500.98210.030*
C20.37653 (16)0.2529 (2)0.97680 (7)0.0235 (5)
C30.46938 (17)0.2221 (3)0.99657 (7)0.0276 (5)
H30.51090.14490.98420.033*
C40.49993 (17)0.3022 (3)1.03328 (7)0.0294 (5)
H40.56310.28201.04540.035*
C50.43829 (17)0.4155 (2)1.05351 (7)0.0262 (5)
C60.46652 (19)0.4978 (3)1.09235 (8)0.0322 (6)
H60.52920.47961.10520.039*
C70.4040 (2)0.6034 (3)1.11137 (8)0.0346 (6)
H70.42380.65801.13720.042*
C80.31011 (19)0.6315 (3)1.09264 (8)0.0341 (6)
H80.26740.70491.10600.041*
C90.28023 (18)0.5536 (3)1.05531 (7)0.0307 (5)
H90.21680.57271.04330.037*
C100.34388 (17)0.4442 (2)1.03449 (7)0.0249 (5)
C110.34585 (16)0.1568 (2)0.93802 (7)0.0241 (5)
C120.27133 (16)0.2170 (2)0.90636 (7)0.0241 (5)
H120.23150.30290.91440.029*
C130.26018 (16)0.1504 (2)0.86644 (7)0.0231 (5)
H130.29760.05950.86090.028*
C140.19583 (16)0.2042 (2)0.83040 (7)0.0220 (5)
C150.22294 (16)0.1705 (2)0.78652 (7)0.0217 (5)
H150.27690.10360.78080.026*
C160.17044 (15)0.2357 (2)0.75135 (7)0.0209 (5)
C170.08824 (16)0.3293 (2)0.75981 (7)0.0222 (5)
C180.05816 (15)0.3542 (2)0.80379 (7)0.0227 (5)
C190.11192 (15)0.2940 (2)0.83896 (7)0.0232 (5)
H190.09200.31350.86860.028*
C200.27906 (17)0.1216 (3)0.69788 (7)0.0276 (5)
H20A0.29050.11970.66580.041*
H20B0.26640.01620.70840.041*
H20C0.33730.16330.71290.041*
C210.05345 (16)0.3410 (3)0.71384 (8)0.0298 (5)
H21A0.07740.38930.68650.045*
H21B0.09940.36310.73810.045*
H21C0.04860.22870.70960.045*
C220.05929 (18)0.4654 (3)0.85373 (8)0.0344 (6)
H22A0.11930.52840.85340.052*
H22B0.00850.51820.87120.052*
H22C0.07360.36440.86700.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0347 (9)0.0252 (8)0.0279 (8)0.0042 (7)0.0054 (7)0.0019 (7)
O20.0263 (8)0.0270 (8)0.0214 (8)0.0041 (7)0.0000 (6)0.0004 (6)
O30.0219 (8)0.0296 (9)0.0279 (8)0.0005 (7)0.0030 (6)0.0069 (6)
O40.0249 (8)0.0331 (9)0.0245 (8)0.0073 (7)0.0013 (6)0.0010 (6)
C10.0266 (12)0.0255 (11)0.0233 (11)0.0021 (9)0.0021 (9)0.0019 (9)
C20.0258 (12)0.0237 (11)0.0209 (11)0.0020 (9)0.0020 (9)0.0022 (9)
C30.0273 (12)0.0282 (12)0.0273 (12)0.0024 (10)0.0018 (9)0.0002 (9)
C40.0273 (13)0.0321 (13)0.0287 (12)0.0027 (10)0.0061 (10)0.0025 (9)
C50.0328 (13)0.0237 (11)0.0220 (11)0.0011 (9)0.0030 (9)0.0023 (8)
C60.0381 (14)0.0313 (13)0.0271 (12)0.0003 (11)0.0098 (10)0.0021 (10)
C70.0499 (16)0.0295 (12)0.0245 (12)0.0007 (11)0.0044 (11)0.0023 (10)
C80.0435 (15)0.0320 (13)0.0268 (12)0.0045 (11)0.0001 (11)0.0035 (10)
C90.0340 (13)0.0297 (12)0.0283 (12)0.0048 (10)0.0045 (10)0.0024 (10)
C100.0319 (12)0.0200 (10)0.0228 (11)0.0000 (9)0.0012 (9)0.0020 (8)
C110.0259 (12)0.0232 (11)0.0233 (11)0.0006 (9)0.0015 (9)0.0032 (9)
C120.0243 (12)0.0223 (11)0.0257 (11)0.0009 (9)0.0005 (9)0.0008 (9)
C130.0229 (11)0.0199 (10)0.0266 (11)0.0004 (9)0.0003 (9)0.0001 (9)
C140.0248 (11)0.0170 (10)0.0241 (11)0.0025 (9)0.0018 (9)0.0006 (8)
C150.0218 (11)0.0175 (10)0.0259 (11)0.0005 (8)0.0002 (9)0.0013 (8)
C160.0214 (11)0.0209 (10)0.0205 (10)0.0030 (8)0.0007 (8)0.0007 (8)
C170.0214 (11)0.0200 (10)0.0253 (11)0.0020 (8)0.0040 (9)0.0037 (8)
C180.0186 (11)0.0207 (10)0.0289 (11)0.0002 (9)0.0009 (9)0.0011 (9)
C190.0239 (11)0.0222 (11)0.0235 (11)0.0007 (9)0.0004 (9)0.0023 (8)
C200.0288 (12)0.0294 (12)0.0246 (11)0.0074 (10)0.0002 (9)0.0028 (9)
C210.0221 (12)0.0378 (13)0.0294 (12)0.0015 (10)0.0056 (9)0.0014 (10)
C220.0313 (13)0.0430 (14)0.0290 (12)0.0116 (11)0.0039 (10)0.0033 (11)
Geometric parameters (Å, º) top
O1—C111.238 (3)C9—C101.427 (3)
O2—C161.374 (2)C9—H90.9500
O2—C201.441 (3)C11—C121.486 (3)
O3—C171.383 (2)C12—C131.343 (3)
O3—C211.442 (3)C12—H120.9500
O4—C181.376 (3)C13—C141.471 (3)
O4—C221.441 (3)C13—H130.9500
C1—C21.380 (3)C14—C191.403 (3)
C1—C101.422 (3)C14—C151.405 (3)
C1—H10.9500C15—C161.397 (3)
C2—C31.421 (3)C15—H150.9500
C2—C111.494 (3)C16—C171.403 (3)
C3—C41.371 (3)C17—C181.405 (3)
C3—H30.9500C18—C191.389 (3)
C4—C51.425 (3)C19—H190.9500
C4—H40.9500C20—H20A0.9800
C5—C61.424 (3)C20—H20B0.9800
C5—C101.427 (3)C20—H20C0.9800
C6—C71.372 (3)C21—H21A0.9800
C6—H60.9500C21—H21B0.9800
C7—C81.416 (4)C21—H21C0.9800
C7—H70.9500C22—H22A0.9800
C8—C91.373 (3)C22—H22B0.9800
C8—H80.9500C22—H22C0.9800
C16—O2—C20116.84 (16)C12—C13—C14126.5 (2)
C17—O3—C21114.41 (16)C12—C13—H13116.8
C18—O4—C22116.55 (17)C14—C13—H13116.8
C2—C1—C10121.1 (2)C19—C14—C15120.07 (19)
C2—C1—H1119.5C19—C14—C13121.46 (19)
C10—C1—H1119.5C15—C14—C13118.39 (19)
C1—C2—C3119.3 (2)C16—C15—C14119.9 (2)
C1—C2—C11122.4 (2)C16—C15—H15120.0
C3—C2—C11118.17 (19)C14—C15—H15120.0
C4—C3—C2120.9 (2)O2—C16—C15124.18 (19)
C4—C3—H3119.6O2—C16—C17115.75 (18)
C2—C3—H3119.6C15—C16—C17120.05 (19)
C3—C4—C5121.0 (2)O3—C17—C16118.93 (19)
C3—C4—H4119.5O3—C17—C18121.49 (19)
C5—C4—H4119.5C16—C17—C18119.47 (19)
C6—C5—C4122.5 (2)O4—C18—C19123.63 (19)
C6—C5—C10119.1 (2)O4—C18—C17115.62 (18)
C4—C5—C10118.39 (19)C19—C18—C17120.72 (19)
C7—C6—C5120.6 (2)C18—C19—C14119.6 (2)
C7—C6—H6119.7C18—C19—H19120.2
C5—C6—H6119.7C14—C19—H19120.2
C6—C7—C8120.3 (2)O2—C20—H20A109.5
C6—C7—H7119.8O2—C20—H20B109.5
C8—C7—H7119.8H20A—C20—H20B109.5
C9—C8—C7120.6 (2)O2—C20—H20C109.5
C9—C8—H8119.7H20A—C20—H20C109.5
C7—C8—H8119.7H20B—C20—H20C109.5
C8—C9—C10120.4 (2)O3—C21—H21A109.5
C8—C9—H9119.8O3—C21—H21B109.5
C10—C9—H9119.8H21A—C21—H21B109.5
C1—C10—C9121.8 (2)O3—C21—H21C109.5
C1—C10—C5119.3 (2)H21A—C21—H21C109.5
C9—C10—C5118.9 (2)H21B—C21—H21C109.5
O1—C11—C12120.8 (2)O4—C22—H22A109.5
O1—C11—C2119.26 (19)O4—C22—H22B109.5
C12—C11—C2119.92 (19)H22A—C22—H22B109.5
C13—C12—C11120.2 (2)O4—C22—H22C109.5
C13—C12—H12119.9H22A—C22—H22C109.5
C11—C12—H12119.9H22B—C22—H22C109.5
C10—C1—C2—C30.9 (3)C11—C12—C13—C14174.7 (2)
C10—C1—C2—C11175.0 (2)C12—C13—C14—C1925.2 (3)
C1—C2—C3—C41.3 (3)C12—C13—C14—C15151.4 (2)
C11—C2—C3—C4177.4 (2)C19—C14—C15—C164.6 (3)
C2—C3—C4—C51.9 (3)C13—C14—C15—C16172.15 (19)
C3—C4—C5—C6178.3 (2)C20—O2—C16—C152.2 (3)
C3—C4—C5—C100.3 (3)C20—O2—C16—C17179.60 (18)
C4—C5—C6—C7178.5 (2)C14—C15—C16—O2175.49 (19)
C10—C5—C6—C70.1 (3)C14—C15—C16—C172.7 (3)
C5—C6—C7—C80.2 (4)C21—O3—C17—C16109.4 (2)
C6—C7—C8—C90.1 (4)C21—O3—C17—C1874.5 (2)
C7—C8—C9—C100.7 (4)O2—C16—C17—O33.4 (3)
C2—C1—C10—C9177.3 (2)C15—C16—C17—O3174.90 (18)
C2—C1—C10—C52.5 (3)O2—C16—C17—C18179.60 (18)
C8—C9—C10—C1179.2 (2)C15—C16—C17—C181.3 (3)
C8—C9—C10—C50.9 (3)C22—O4—C18—C194.3 (3)
C6—C5—C10—C1179.5 (2)C22—O4—C18—C17177.42 (19)
C4—C5—C10—C11.9 (3)O3—C17—C18—O45.6 (3)
C6—C5—C10—C90.6 (3)C16—C17—C18—O4178.26 (18)
C4—C5—C10—C9178.0 (2)O3—C17—C18—C19172.67 (19)
C1—C2—C11—O1154.3 (2)C16—C17—C18—C193.4 (3)
C3—C2—C11—O121.7 (3)O4—C18—C19—C14179.73 (19)
C1—C2—C11—C1226.7 (3)C17—C18—C19—C141.5 (3)
C3—C2—C11—C12157.3 (2)C15—C14—C19—C182.5 (3)
O1—C11—C12—C1314.8 (3)C13—C14—C19—C18174.16 (19)
C2—C11—C12—C13164.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.952.563.508 (3)176
C22—H22B···O1i0.982.513.405 (3)153
Symmetry code: (i) x+1/2, y+1/2, z.
 

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