(E)-1-(2-Naphthyl)-3-(3,4,5-trimethoxy­phen­yl)prop-2-en-1-one

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.

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

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Computing details

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

Crystal data

C22H20O4	Dx = 1.307 Mg m^−3
Mr = 348.38	Melting point: 392-393K K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5952 reflections
a = 13.5903 (13) Å	θ = 1.4–27.1°
b = 8.6378 (9) Å	µ = 0.09 mm^−1
c = 30.169 (3) Å	T = 113 K
V = 3541.5 (6) Å^3	Platelet, colorless
Z = 8	0.34 × 0.22 × 0.06 mm
F(000) = 1472

Data collection

Rigaku Saturn-70 diffractometer	3229 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.073
Confocal monochromator	θmax = 26.0°, θmin = 1.3°
Detector resolution: 7.31 pixels mm^-1	h = −16→16
ω scans	k = −10→9
26883 measured reflections	l = −37→37
3477 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.146	w = 1/[σ^2(Fo^2) + (0.0553P)^2 + 1.8606P] where P = (Fo^2 + 2Fc^2)/3
S = 1.23	(Δ/σ)max = 0.001
3477 reflections	Δρmax = 0.22 e Å^−3
240 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.38413 (12)	0.02823 (17)	0.93239 (5)	0.0293 (4)
O2	0.19524 (11)	0.21810 (17)	0.70749 (5)	0.0249 (4)
O3	0.04222 (11)	0.40238 (17)	0.72466 (5)	0.0265 (4)
O4	−0.02470 (11)	0.44389 (18)	0.80901 (5)	0.0275 (4)
C1	0.31570 (16)	0.3630 (2)	0.99549 (7)	0.0252 (5)
H1	0.2540	0.3850	0.9821	0.030*
C2	0.37653 (16)	0.2529 (2)	0.97680 (7)	0.0235 (5)
C3	0.46938 (17)	0.2221 (3)	0.99657 (7)	0.0276 (5)
H3	0.5109	0.1449	0.9842	0.033*
C4	0.49993 (17)	0.3022 (3)	1.03328 (7)	0.0294 (5)
H4	0.5631	0.2820	1.0454	0.035*
C5	0.43829 (17)	0.4155 (2)	1.05351 (7)	0.0262 (5)
C6	0.46652 (19)	0.4978 (3)	1.09235 (8)	0.0322 (6)
H6	0.5292	0.4796	1.1052	0.039*
C7	0.4040 (2)	0.6034 (3)	1.11137 (8)	0.0346 (6)
H7	0.4238	0.6580	1.1372	0.042*
C8	0.31011 (19)	0.6315 (3)	1.09264 (8)	0.0341 (6)
H8	0.2674	0.7049	1.1060	0.041*
C9	0.28023 (18)	0.5536 (3)	1.05531 (7)	0.0307 (5)
H9	0.2168	0.5727	1.0433	0.037*
C10	0.34388 (17)	0.4442 (2)	1.03449 (7)	0.0249 (5)
C11	0.34585 (16)	0.1568 (2)	0.93802 (7)	0.0241 (5)
C12	0.27133 (16)	0.2170 (2)	0.90636 (7)	0.0241 (5)
H12	0.2315	0.3029	0.9144	0.029*
C13	0.26018 (16)	0.1504 (2)	0.86644 (7)	0.0231 (5)
H13	0.2976	0.0595	0.8609	0.028*
C14	0.19583 (16)	0.2042 (2)	0.83040 (7)	0.0220 (5)
C15	0.22294 (16)	0.1705 (2)	0.78652 (7)	0.0217 (5)
H15	0.2769	0.1036	0.7808	0.026*
C16	0.17044 (15)	0.2357 (2)	0.75135 (7)	0.0209 (5)
C17	0.08824 (16)	0.3293 (2)	0.75981 (7)	0.0222 (5)
C18	0.05816 (15)	0.3542 (2)	0.80379 (7)	0.0227 (5)
C19	0.11192 (15)	0.2940 (2)	0.83896 (7)	0.0232 (5)
H19	0.0920	0.3135	0.8686	0.028*
C20	0.27906 (17)	0.1216 (3)	0.69788 (7)	0.0276 (5)
H20A	0.2905	0.1197	0.6658	0.041*
H20B	0.2664	0.0162	0.7084	0.041*
H20C	0.3373	0.1633	0.7129	0.041*
C21	−0.05345 (16)	0.3410 (3)	0.71384 (8)	0.0298 (5)
H21A	−0.0774	0.3893	0.6865	0.045*
H21B	−0.0994	0.3631	0.7381	0.045*
H21C	−0.0486	0.2287	0.7096	0.045*
C22	−0.05929 (18)	0.4654 (3)	0.85373 (8)	0.0344 (6)
H22A	−0.1193	0.5284	0.8534	0.052*
H22B	−0.0085	0.5182	0.8712	0.052*
H22C	−0.0736	0.3644	0.8670	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0347 (9)	0.0252 (8)	0.0279 (8)	0.0042 (7)	−0.0054 (7)	−0.0019 (7)
O2	0.0263 (8)	0.0270 (8)	0.0214 (8)	0.0041 (7)	0.0000 (6)	0.0004 (6)
O3	0.0219 (8)	0.0296 (9)	0.0279 (8)	−0.0005 (7)	−0.0030 (6)	0.0069 (6)
O4	0.0249 (8)	0.0331 (9)	0.0245 (8)	0.0073 (7)	0.0013 (6)	0.0010 (6)
C1	0.0266 (12)	0.0255 (11)	0.0233 (11)	0.0021 (9)	−0.0021 (9)	0.0019 (9)
C2	0.0258 (12)	0.0237 (11)	0.0209 (11)	−0.0020 (9)	−0.0020 (9)	0.0022 (9)
C3	0.0273 (12)	0.0282 (12)	0.0273 (12)	0.0024 (10)	−0.0018 (9)	0.0002 (9)
C4	0.0273 (13)	0.0321 (13)	0.0287 (12)	0.0027 (10)	−0.0061 (10)	0.0025 (9)
C5	0.0328 (13)	0.0237 (11)	0.0220 (11)	−0.0011 (9)	−0.0030 (9)	0.0023 (8)
C6	0.0381 (14)	0.0313 (13)	0.0271 (12)	−0.0003 (11)	−0.0098 (10)	0.0021 (10)
C7	0.0499 (16)	0.0295 (12)	0.0245 (12)	−0.0007 (11)	−0.0044 (11)	−0.0023 (10)
C8	0.0435 (15)	0.0320 (13)	0.0268 (12)	0.0045 (11)	0.0001 (11)	−0.0035 (10)
C9	0.0340 (13)	0.0297 (12)	0.0283 (12)	0.0048 (10)	−0.0045 (10)	0.0024 (10)
C10	0.0319 (12)	0.0200 (10)	0.0228 (11)	0.0000 (9)	−0.0012 (9)	0.0020 (8)
C11	0.0259 (12)	0.0232 (11)	0.0233 (11)	−0.0006 (9)	0.0015 (9)	0.0032 (9)
C12	0.0243 (12)	0.0223 (11)	0.0257 (11)	0.0009 (9)	0.0005 (9)	0.0008 (9)
C13	0.0229 (11)	0.0199 (10)	0.0266 (11)	0.0004 (9)	−0.0003 (9)	0.0001 (9)
C14	0.0248 (11)	0.0170 (10)	0.0241 (11)	−0.0025 (9)	−0.0018 (9)	0.0006 (8)
C15	0.0218 (11)	0.0175 (10)	0.0259 (11)	−0.0005 (8)	0.0002 (9)	−0.0013 (8)
C16	0.0214 (11)	0.0209 (10)	0.0205 (10)	−0.0030 (8)	−0.0007 (8)	−0.0007 (8)
C17	0.0214 (11)	0.0200 (10)	0.0253 (11)	−0.0020 (8)	−0.0040 (9)	0.0037 (8)
C18	0.0186 (11)	0.0207 (10)	0.0289 (11)	0.0002 (9)	−0.0009 (9)	−0.0011 (9)
C19	0.0239 (11)	0.0222 (11)	0.0235 (11)	−0.0007 (9)	0.0004 (9)	−0.0023 (8)
C20	0.0288 (12)	0.0294 (12)	0.0246 (11)	0.0074 (10)	0.0002 (9)	−0.0028 (9)
C21	0.0221 (12)	0.0378 (13)	0.0294 (12)	−0.0015 (10)	−0.0056 (9)	0.0014 (10)
C22	0.0313 (13)	0.0430 (14)	0.0290 (12)	0.0116 (11)	0.0039 (10)	−0.0033 (11)

Geometric parameters (Å, º)

O1—C11	1.238 (3)	C9—C10	1.427 (3)
O2—C16	1.374 (2)	C9—H9	0.9500
O2—C20	1.441 (3)	C11—C12	1.486 (3)
O3—C17	1.383 (2)	C12—C13	1.343 (3)
O3—C21	1.442 (3)	C12—H12	0.9500
O4—C18	1.376 (3)	C13—C14	1.471 (3)
O4—C22	1.441 (3)	C13—H13	0.9500
C1—C2	1.380 (3)	C14—C19	1.403 (3)
C1—C10	1.422 (3)	C14—C15	1.405 (3)
C1—H1	0.9500	C15—C16	1.397 (3)
C2—C3	1.421 (3)	C15—H15	0.9500
C2—C11	1.494 (3)	C16—C17	1.403 (3)
C3—C4	1.371 (3)	C17—C18	1.405 (3)
C3—H3	0.9500	C18—C19	1.389 (3)
C4—C5	1.425 (3)	C19—H19	0.9500
C4—H4	0.9500	C20—H20A	0.9800
C5—C6	1.424 (3)	C20—H20B	0.9800
C5—C10	1.427 (3)	C20—H20C	0.9800
C6—C7	1.372 (3)	C21—H21A	0.9800
C6—H6	0.9500	C21—H21B	0.9800
C7—C8	1.416 (4)	C21—H21C	0.9800
C7—H7	0.9500	C22—H22A	0.9800
C8—C9	1.373 (3)	C22—H22B	0.9800
C8—H8	0.9500	C22—H22C	0.9800
C16—O2—C20	116.84 (16)	C12—C13—C14	126.5 (2)
C17—O3—C21	114.41 (16)	C12—C13—H13	116.8
C18—O4—C22	116.55 (17)	C14—C13—H13	116.8
C2—C1—C10	121.1 (2)	C19—C14—C15	120.07 (19)
C2—C1—H1	119.5	C19—C14—C13	121.46 (19)
C10—C1—H1	119.5	C15—C14—C13	118.39 (19)
C1—C2—C3	119.3 (2)	C16—C15—C14	119.9 (2)
C1—C2—C11	122.4 (2)	C16—C15—H15	120.0
C3—C2—C11	118.17 (19)	C14—C15—H15	120.0
C4—C3—C2	120.9 (2)	O2—C16—C15	124.18 (19)
C4—C3—H3	119.6	O2—C16—C17	115.75 (18)
C2—C3—H3	119.6	C15—C16—C17	120.05 (19)
C3—C4—C5	121.0 (2)	O3—C17—C16	118.93 (19)
C3—C4—H4	119.5	O3—C17—C18	121.49 (19)
C5—C4—H4	119.5	C16—C17—C18	119.47 (19)
C6—C5—C4	122.5 (2)	O4—C18—C19	123.63 (19)
C6—C5—C10	119.1 (2)	O4—C18—C17	115.62 (18)
C4—C5—C10	118.39 (19)	C19—C18—C17	120.72 (19)
C7—C6—C5	120.6 (2)	C18—C19—C14	119.6 (2)
C7—C6—H6	119.7	C18—C19—H19	120.2
C5—C6—H6	119.7	C14—C19—H19	120.2
C6—C7—C8	120.3 (2)	O2—C20—H20A	109.5
C6—C7—H7	119.8	O2—C20—H20B	109.5
C8—C7—H7	119.8	H20A—C20—H20B	109.5
C9—C8—C7	120.6 (2)	O2—C20—H20C	109.5
C9—C8—H8	119.7	H20A—C20—H20C	109.5
C7—C8—H8	119.7	H20B—C20—H20C	109.5
C8—C9—C10	120.4 (2)	O3—C21—H21A	109.5
C8—C9—H9	119.8	O3—C21—H21B	109.5
C10—C9—H9	119.8	H21A—C21—H21B	109.5
C1—C10—C9	121.8 (2)	O3—C21—H21C	109.5
C1—C10—C5	119.3 (2)	H21A—C21—H21C	109.5
C9—C10—C5	118.9 (2)	H21B—C21—H21C	109.5
O1—C11—C12	120.8 (2)	O4—C22—H22A	109.5
O1—C11—C2	119.26 (19)	O4—C22—H22B	109.5
C12—C11—C2	119.92 (19)	H22A—C22—H22B	109.5
C13—C12—C11	120.2 (2)	O4—C22—H22C	109.5
C13—C12—H12	119.9	H22A—C22—H22C	109.5
C11—C12—H12	119.9	H22B—C22—H22C	109.5
C10—C1—C2—C3	−0.9 (3)	C11—C12—C13—C14	−174.7 (2)
C10—C1—C2—C11	175.0 (2)	C12—C13—C14—C19	−25.2 (3)
C1—C2—C3—C4	−1.3 (3)	C12—C13—C14—C15	151.4 (2)
C11—C2—C3—C4	−177.4 (2)	C19—C14—C15—C16	4.6 (3)
C2—C3—C4—C5	1.9 (3)	C13—C14—C15—C16	−172.15 (19)
C3—C4—C5—C6	178.3 (2)	C20—O2—C16—C15	2.2 (3)
C3—C4—C5—C10	−0.3 (3)	C20—O2—C16—C17	−179.60 (18)
C4—C5—C6—C7	−178.5 (2)	C14—C15—C16—O2	175.49 (19)
C10—C5—C6—C7	0.1 (3)	C14—C15—C16—C17	−2.7 (3)
C5—C6—C7—C8	0.2 (4)	C21—O3—C17—C16	109.4 (2)
C6—C7—C8—C9	0.1 (4)	C21—O3—C17—C18	−74.5 (2)
C7—C8—C9—C10	−0.7 (4)	O2—C16—C17—O3	−3.4 (3)
C2—C1—C10—C9	−177.3 (2)	C15—C16—C17—O3	174.90 (18)
C2—C1—C10—C5	2.5 (3)	O2—C16—C17—C18	−179.60 (18)
C8—C9—C10—C1	−179.2 (2)	C15—C16—C17—C18	−1.3 (3)
C8—C9—C10—C5	0.9 (3)	C22—O4—C18—C19	−4.3 (3)
C6—C5—C10—C1	179.5 (2)	C22—O4—C18—C17	177.42 (19)
C4—C5—C10—C1	−1.9 (3)	O3—C17—C18—O4	5.6 (3)
C6—C5—C10—C9	−0.6 (3)	C16—C17—C18—O4	−178.26 (18)
C4—C5—C10—C9	178.0 (2)	O3—C17—C18—C19	−172.67 (19)
C1—C2—C11—O1	−154.3 (2)	C16—C17—C18—C19	3.4 (3)
C3—C2—C11—O1	21.7 (3)	O4—C18—C19—C14	−179.73 (19)
C1—C2—C11—C12	26.7 (3)	C17—C18—C19—C14	−1.5 (3)
C3—C2—C11—C12	−157.3 (2)	C15—C14—C19—C18	−2.5 (3)
O1—C11—C12—C13	−14.8 (3)	C13—C14—C19—C18	174.16 (19)
C2—C11—C12—C13	164.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1^i	0.95	2.56	3.508 (3)	176
C22—H22B···O1^i	0.98	2.51	3.405 (3)	153

Symmetry code: (i) −x+1/2, y+1/2, z.