(E)-3-(3-Hydr­oxy-4-methoxy­phen­yl)-1-(2-naphth­yl)prop-2-en-1-one

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.

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

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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, 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

Crystal data

C20H16O3	Dx = 1.360 Mg m^−3
Mr = 304.33	Melting point = 442–443 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5205 reflections
a = 14.7417 (11) Å	θ = 1.2–27.8°
b = 6.1208 (4) Å	µ = 0.09 mm^−1
c = 32.941 (3) Å	T = 293 K
V = 2972.3 (4) Å^3	Prism, colorless
Z = 8	0.22 × 0.16 × 0.14 mm
F(000) = 1280

Data collection

Rigaku Saturn-70 diffractometer	3509 independent reflections
Radiation source: rotating anode	3105 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.058
Detector resolution: 7.31 pixels mm^-1	θmax = 27.8°, θmin = 1.2°
ω scans	h = −18→19
Absorption correction: multi-scan (Jacobson, 1998)	k = −8→7
Tmin = 0.980, Tmax = 0.987	l = −42→43
25516 measured 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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0656P)^2 + 0.9426P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.001
3509 reflections	Δρmax = 0.24 e Å^−3
215 parameters	Δρmin = −0.18 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: 0.0075 (13)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O3	0.09127 (10)	0.5675 (2)	0.40742 (4)	0.0382 (3)
O1	0.02783 (9)	0.1139 (2)	0.60903 (3)	0.0317 (3)
O2	0.11988 (9)	−0.2472 (2)	0.61062 (4)	0.0331 (3)
C1	0.06980 (11)	0.0551 (3)	0.57363 (5)	0.0252 (4)
C2	0.11872 (11)	−0.1418 (3)	0.57394 (5)	0.0262 (4)
C3	0.16179 (12)	−0.2137 (3)	0.53859 (5)	0.0284 (4)
H3	0.1933	−0.3453	0.5386	0.034*
C4	0.15766 (11)	−0.0889 (3)	0.50323 (5)	0.0279 (4)
H4	0.1854	−0.1394	0.4797	0.033*
C5	0.11206 (11)	0.1119 (3)	0.50287 (5)	0.0252 (4)
C6	0.06853 (11)	0.1803 (3)	0.53875 (5)	0.0256 (4)
H6	0.0381	0.3134	0.5390	0.031*
C7	0.17932 (13)	−0.4303 (3)	0.61467 (6)	0.0349 (4)
H7A	0.1786	−0.4807	0.6423	0.052*
H7B	0.2399	−0.3876	0.6074	0.052*
H7C	0.1595	−0.5456	0.5970	0.052*
C8	0.10690 (11)	0.2547 (3)	0.46749 (5)	0.0270 (4)
H8	0.0849	0.3946	0.4725	0.032*
C9	0.12943 (12)	0.2127 (3)	0.42870 (5)	0.0278 (4)
H9	0.1552	0.0791	0.4217	0.033*
C10	0.11309 (11)	0.3796 (3)	0.39727 (5)	0.0266 (4)
C11	0.12220 (10)	0.3229 (3)	0.35323 (5)	0.0232 (3)
C12	0.09574 (10)	0.4750 (3)	0.32456 (5)	0.0228 (3)
H12	0.0713	0.6073	0.3331	0.027*
C13	0.10488 (10)	0.4342 (3)	0.28232 (5)	0.0211 (3)
C14	0.07786 (10)	0.5896 (3)	0.25245 (5)	0.0225 (3)
H14	0.0526	0.7218	0.2605	0.027*
C15	0.08881 (11)	0.5459 (3)	0.21185 (5)	0.0260 (4)
H15	0.0705	0.6480	0.1926	0.031*
C16	0.12782 (11)	0.3466 (3)	0.19925 (5)	0.0278 (4)
H16	0.1352	0.3188	0.1717	0.033*
C17	0.15500 (11)	0.1933 (3)	0.22713 (5)	0.0253 (4)
H17	0.1811	0.0633	0.2183	0.030*
C18	0.14347 (10)	0.2320 (3)	0.26949 (5)	0.0213 (3)
C19	0.16910 (10)	0.0762 (3)	0.29935 (5)	0.0242 (4)
H19	0.1934	−0.0571	0.2913	0.029*
C20	0.15854 (11)	0.1198 (3)	0.34000 (5)	0.0252 (4)
H20	0.1753	0.0153	0.3591	0.030*
H1	−0.0129 (19)	0.229 (4)	0.6044 (7)	0.066 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0558 (8)	0.0351 (7)	0.0239 (6)	0.0164 (6)	0.0002 (6)	−0.0034 (5)
O1	0.0381 (7)	0.0362 (7)	0.0208 (6)	0.0085 (6)	0.0041 (5)	−0.0005 (5)
O2	0.0411 (7)	0.0312 (7)	0.0268 (7)	0.0065 (5)	0.0039 (5)	0.0065 (5)
C1	0.0248 (8)	0.0297 (9)	0.0212 (8)	0.0005 (7)	−0.0010 (6)	−0.0037 (6)
C2	0.0277 (8)	0.0275 (9)	0.0235 (8)	−0.0017 (7)	−0.0025 (6)	0.0020 (6)
C3	0.0290 (8)	0.0265 (9)	0.0298 (9)	0.0023 (7)	0.0010 (7)	−0.0014 (7)
C4	0.0283 (8)	0.0315 (9)	0.0238 (8)	0.0018 (7)	0.0018 (6)	−0.0032 (7)
C5	0.0236 (8)	0.0302 (9)	0.0218 (8)	−0.0001 (6)	−0.0026 (6)	−0.0015 (7)
C6	0.0266 (8)	0.0274 (8)	0.0227 (8)	0.0037 (7)	−0.0029 (6)	−0.0020 (7)
C7	0.0468 (11)	0.0240 (9)	0.0338 (10)	0.0050 (8)	−0.0011 (8)	0.0054 (7)
C8	0.0251 (8)	0.0317 (9)	0.0243 (8)	0.0037 (7)	−0.0006 (6)	−0.0012 (7)
C9	0.0291 (8)	0.0311 (9)	0.0234 (8)	0.0039 (7)	−0.0011 (6)	−0.0006 (7)
C10	0.0261 (8)	0.0305 (9)	0.0231 (8)	0.0042 (7)	−0.0004 (6)	−0.0028 (7)
C11	0.0208 (7)	0.0266 (8)	0.0223 (8)	0.0024 (6)	−0.0003 (6)	−0.0014 (6)
C12	0.0216 (7)	0.0234 (8)	0.0233 (8)	0.0015 (6)	0.0001 (6)	−0.0034 (6)
C13	0.0176 (7)	0.0239 (8)	0.0219 (8)	−0.0011 (6)	−0.0001 (6)	−0.0018 (6)
C14	0.0213 (7)	0.0221 (8)	0.0241 (8)	0.0011 (6)	0.0001 (6)	−0.0017 (6)
C15	0.0250 (8)	0.0290 (9)	0.0239 (8)	−0.0013 (7)	0.0000 (6)	0.0027 (7)
C16	0.0288 (8)	0.0351 (10)	0.0196 (8)	−0.0032 (7)	0.0034 (6)	−0.0039 (7)
C17	0.0246 (8)	0.0266 (8)	0.0245 (8)	0.0008 (7)	0.0013 (6)	−0.0056 (7)
C18	0.0177 (7)	0.0242 (8)	0.0220 (8)	−0.0005 (6)	0.0002 (6)	−0.0022 (6)
C19	0.0221 (7)	0.0237 (8)	0.0267 (8)	0.0023 (6)	0.0007 (6)	−0.0028 (6)
C20	0.0239 (8)	0.0262 (8)	0.0256 (8)	0.0035 (6)	−0.0015 (6)	0.0013 (7)

Geometric parameters (Å, º)

O3—C10	1.240 (2)	C9—H9	0.9300
O1—C1	1.3682 (19)	C10—C11	1.498 (2)
O1—H1	0.94 (3)	C11—C12	1.382 (2)
O2—C2	1.370 (2)	C11—C20	1.422 (2)
O2—C7	1.429 (2)	C12—C13	1.420 (2)
C1—C6	1.381 (2)	C12—H12	0.9300
C1—C2	1.405 (2)	C13—C14	1.425 (2)
C2—C3	1.397 (2)	C13—C18	1.427 (2)
C3—C4	1.394 (2)	C14—C15	1.374 (2)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.401 (2)	C15—C16	1.411 (2)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.409 (2)	C16—C17	1.373 (2)
C5—C8	1.459 (2)	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.425 (2)
C7—H7A	0.9600	C17—H17	0.9300
C7—H7B	0.9600	C18—C19	1.421 (2)
C7—H7C	0.9600	C19—C20	1.374 (2)
C8—C9	1.345 (2)	C19—H19	0.9300
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.475 (2)
C1—O1—H1	110.3 (15)	O3—C10—C11	119.96 (16)
C2—O2—C7	117.33 (13)	C9—C10—C11	120.31 (15)
O1—C1—C6	123.85 (15)	C12—C11—C20	119.06 (15)
O1—C1—C2	116.85 (15)	C12—C11—C10	118.71 (15)
C6—C1—C2	119.28 (15)	C20—C11—C10	122.22 (15)
O2—C2—C3	125.52 (16)	C11—C12—C13	121.63 (15)
O2—C2—C1	114.63 (14)	C11—C12—H12	119.2
C3—C2—C1	119.84 (15)	C13—C12—H12	119.2
C4—C3—C2	120.23 (16)	C12—C13—C14	122.20 (15)
C4—C3—H3	119.9	C12—C13—C18	118.73 (14)
C2—C3—H3	119.9	C14—C13—C18	119.07 (14)
C3—C4—C5	120.59 (15)	C15—C14—C13	120.65 (15)
C3—C4—H4	119.7	C15—C14—H14	119.7
C5—C4—H4	119.7	C13—C14—H14	119.7
C4—C5—C6	118.18 (15)	C14—C15—C16	120.16 (15)
C4—C5—C8	123.89 (15)	C14—C15—H15	119.9
C6—C5—C8	117.92 (15)	C16—C15—H15	119.9
C1—C6—C5	121.80 (16)	C17—C16—C15	120.88 (15)
C1—C6—H6	119.1	C17—C16—H16	119.6
C5—C6—H6	119.1	C15—C16—H16	119.6
O2—C7—H7A	109.5	C16—C17—C18	120.41 (15)
O2—C7—H7B	109.5	C16—C17—H17	119.8
H7A—C7—H7B	109.5	C18—C17—H17	119.8
O2—C7—H7C	109.5	C19—C18—C17	122.30 (15)
H7A—C7—H7C	109.5	C19—C18—C13	118.88 (14)
H7B—C7—H7C	109.5	C17—C18—C13	118.82 (15)
C9—C8—C5	129.14 (17)	C20—C19—C18	120.96 (15)
C9—C8—H8	115.4	C20—C19—H19	119.5
C5—C8—H8	115.4	C18—C19—H19	119.5
C8—C9—C10	119.60 (16)	C19—C20—C11	120.71 (15)
C8—C9—H9	120.2	C19—C20—H20	119.6
C10—C9—H9	120.2	C11—C20—H20	119.6
O3—C10—C9	119.73 (15)
C7—O2—C2—C3	8.6 (2)	O3—C10—C11—C20	171.43 (16)
C7—O2—C2—C1	−170.85 (15)	C9—C10—C11—C20	−8.9 (2)
O1—C1—C2—O2	−1.8 (2)	C20—C11—C12—C13	−0.7 (2)
C6—C1—C2—O2	176.46 (15)	C10—C11—C12—C13	178.23 (14)
O1—C1—C2—C3	178.78 (15)	C11—C12—C13—C14	179.98 (14)
C6—C1—C2—C3	−3.0 (2)	C11—C12—C13—C18	−0.8 (2)
O2—C2—C3—C4	−178.32 (16)	C12—C13—C14—C15	179.12 (15)
C1—C2—C3—C4	1.1 (3)	C18—C13—C14—C15	−0.1 (2)
C2—C3—C4—C5	1.4 (3)	C13—C14—C15—C16	−0.5 (2)
C3—C4—C5—C6	−1.8 (2)	C14—C15—C16—C17	0.3 (2)
C3—C4—C5—C8	178.19 (16)	C15—C16—C17—C18	0.6 (2)
O1—C1—C6—C5	−179.37 (15)	C16—C17—C18—C19	178.84 (15)
C2—C1—C6—C5	2.5 (2)	C16—C17—C18—C13	−1.2 (2)
C4—C5—C6—C1	−0.1 (2)	C12—C13—C18—C19	1.7 (2)
C8—C5—C6—C1	179.84 (15)	C14—C13—C18—C19	−179.09 (14)
C4—C5—C8—C9	11.8 (3)	C12—C13—C18—C17	−178.30 (14)
C6—C5—C8—C9	−168.24 (17)	C14—C13—C18—C17	0.9 (2)
C5—C8—C9—C10	176.28 (16)	C17—C18—C19—C20	178.90 (15)
C8—C9—C10—O3	10.4 (3)	C13—C18—C19—C20	−1.1 (2)
C8—C9—C10—C11	−169.21 (15)	C18—C19—C20—C11	−0.4 (2)
O3—C10—C11—C12	−7.5 (2)	C12—C11—C20—C19	1.3 (2)
C9—C10—C11—C12	172.18 (15)	C10—C11—C20—C19	−177.55 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.94 (3)	1.74 (3)	2.6795 (18)	176 (2)

Symmetry code: (i) −x, −y+1, −z+1.