(2E)-3-(6-Meth­oxy-2-naphth­yl)-1-phenyl­prop-2-en-1-one

The geometric parameters of the title compound, C₂₀H₁₆O₂, are in the usual ranges. The central double bond is trans configured. Its two C atoms are slightly twisted out of the naphthyl plane. The dihedral angle between the aromatic groups is 14.09 (8)°.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.097
• Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.64

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.62
           From the CIF: _reflns_number_total               1535
           Count of symmetry unique reflns         1550
           Completeness (_total/calc)             99.03%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

(2E)-3-(6-Methoxy-2-naphthyl)-1-phenylprop-2-en-1-one

Crystal data

C20H16O2	F(000) = 608
Mr = 288.33	Dx = 1.286 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 6589 reflections
a = 14.5275 (17) Å	θ = 3.6–25.7°
b = 17.0930 (15) Å	µ = 0.08 mm^−1
c = 5.9950 (5) Å	T = 173 K
V = 1488.7 (3) Å^3	Plate, light yellow
Z = 4	0.27 × 0.24 × 0.13 mm

Data collection

Stoe IPDS II two-circle diffractometer	1367 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.089
Graphite monochromator	θmax = 25.6°, θmin = 3.6°
ω scans	h = −17→16
7578 measured reflections	k = −20→19
1535 independent reflections	l = −6→7

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0648P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.097	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.21 e Å^−3
1535 reflections	Δρmin = −0.21 e Å^−3
201 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.029 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map

Special details

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	0.37130 (13)	0.22873 (9)	−0.1380 (3)	0.0403 (5)
O2	0.37831 (12)	0.79747 (8)	0.5452 (3)	0.0415 (5)
C1	0.37084 (16)	0.21836 (13)	0.0657 (4)	0.0329 (5)
C2	0.36629 (14)	0.28599 (12)	0.2221 (4)	0.0322 (5)
H2	0.3505	0.2782	0.3742	0.039*
C3	0.38482 (14)	0.35825 (12)	0.1454 (4)	0.0298 (5)
H3	0.4027	0.3614	−0.0068	0.036*
C11	0.37468 (14)	0.13644 (12)	0.1566 (4)	0.0311 (5)
C12	0.34204 (15)	0.11650 (13)	0.3689 (4)	0.0334 (5)
H12	0.3209	0.1561	0.4675	0.040*
C13	0.34061 (16)	0.03825 (13)	0.4353 (5)	0.0404 (6)
H13	0.3162	0.0246	0.5770	0.049*
C14	0.37466 (16)	−0.01990 (13)	0.2957 (5)	0.0405 (6)
H14	0.3736	−0.0731	0.3419	0.049*
C15	0.41040 (16)	0.00020 (13)	0.0874 (5)	0.0410 (6)
H15	0.4357	−0.0391	−0.0065	0.049*
C16	0.40897 (16)	0.07731 (12)	0.0176 (4)	0.0371 (6)
H16	0.4315	0.0904	−0.1264	0.044*
C21	0.38092 (13)	0.43256 (11)	0.2659 (4)	0.0259 (4)
C22	0.41303 (13)	0.49981 (11)	0.1629 (4)	0.0276 (5)
H22	0.4410	0.4956	0.0202	0.033*
C23	0.40556 (13)	0.57445 (11)	0.2629 (4)	0.0259 (4)
C24	0.43940 (14)	0.64382 (11)	0.1589 (4)	0.0312 (5)
H24	0.4690	0.6403	0.0179	0.037*
C25	0.42992 (15)	0.71545 (11)	0.2588 (5)	0.0329 (5)
H25	0.4535	0.7609	0.1878	0.039*
C26	0.38498 (15)	0.72185 (11)	0.4684 (4)	0.0321 (5)
C27	0.35081 (14)	0.65655 (12)	0.5760 (4)	0.0298 (5)
H27	0.3197	0.6618	0.7147	0.036*
C28	0.36256 (13)	0.58136 (12)	0.4776 (4)	0.0259 (5)
C29	0.33145 (14)	0.51131 (12)	0.5841 (4)	0.0275 (5)
H29	0.3035	0.5145	0.7271	0.033*
C30	0.34108 (13)	0.43967 (12)	0.4842 (4)	0.0273 (5)
H30	0.3211	0.3940	0.5605	0.033*
C31	0.3252 (2)	0.81078 (13)	0.7438 (5)	0.0492 (7)
H31A	0.2633	0.7892	0.7241	0.074*
H31B	0.3210	0.8671	0.7721	0.074*
H31C	0.3552	0.7851	0.8706	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0494 (11)	0.0378 (8)	0.0337 (10)	−0.0068 (7)	0.0022 (8)	−0.0034 (7)
O2	0.0502 (10)	0.0267 (7)	0.0477 (11)	−0.0011 (6)	0.0008 (9)	−0.0035 (7)
C1	0.0261 (12)	0.0369 (11)	0.0356 (14)	−0.0033 (8)	0.0030 (10)	−0.0026 (10)
C2	0.0295 (11)	0.0311 (10)	0.0359 (14)	−0.0005 (8)	0.0026 (10)	−0.0038 (9)
C3	0.0214 (10)	0.0370 (11)	0.0312 (12)	0.0021 (8)	−0.0014 (9)	−0.0024 (9)
C11	0.0233 (11)	0.0320 (10)	0.0381 (13)	−0.0023 (8)	−0.0017 (10)	−0.0047 (10)
C12	0.0301 (12)	0.0360 (11)	0.0342 (13)	0.0014 (9)	0.0023 (10)	−0.0015 (10)
C13	0.0392 (13)	0.0421 (13)	0.0400 (15)	−0.0029 (10)	0.0002 (12)	0.0047 (11)
C14	0.0344 (12)	0.0299 (11)	0.0573 (18)	−0.0004 (9)	−0.0077 (12)	0.0019 (11)
C15	0.0353 (12)	0.0340 (11)	0.0537 (16)	0.0008 (10)	0.0009 (12)	−0.0103 (11)
C16	0.0337 (12)	0.0387 (11)	0.0389 (15)	−0.0040 (9)	0.0046 (11)	−0.0072 (10)
C21	0.0189 (9)	0.0273 (9)	0.0314 (12)	0.0012 (7)	−0.0024 (9)	0.0015 (9)
C22	0.0190 (10)	0.0370 (11)	0.0268 (11)	0.0023 (8)	0.0010 (9)	0.0021 (8)
C23	0.0190 (9)	0.0295 (9)	0.0292 (11)	0.0010 (7)	−0.0011 (9)	0.0040 (9)
C24	0.0231 (11)	0.0379 (11)	0.0326 (12)	0.0012 (8)	0.0030 (10)	0.0075 (9)
C25	0.0289 (11)	0.0295 (10)	0.0403 (12)	−0.0028 (8)	−0.0001 (11)	0.0103 (10)
C26	0.0313 (11)	0.0267 (10)	0.0383 (13)	−0.0015 (8)	−0.0034 (11)	0.0003 (10)
C27	0.0253 (11)	0.0332 (10)	0.0310 (12)	0.0006 (8)	−0.0009 (9)	−0.0013 (10)
C28	0.0195 (9)	0.0296 (10)	0.0285 (11)	0.0000 (7)	−0.0026 (10)	0.0015 (9)
C29	0.0221 (10)	0.0312 (10)	0.0293 (11)	0.0005 (8)	0.0011 (9)	0.0011 (9)
C30	0.0232 (10)	0.0286 (10)	0.0300 (12)	−0.0010 (7)	−0.0011 (10)	0.0036 (9)
C31	0.0756 (19)	0.0310 (11)	0.0409 (15)	0.0043 (11)	0.0040 (15)	−0.0068 (12)

Geometric parameters (Å, º)

O1—C1	1.234 (3)	C21—C22	1.386 (3)
O2—C26	1.376 (2)	C21—C30	1.436 (3)
O2—C31	1.436 (3)	C22—C23	1.414 (3)
C1—C2	1.490 (3)	C22—H22	0.9500
C1—C11	1.503 (3)	C23—C24	1.427 (3)
C2—C3	1.345 (3)	C23—C28	1.435 (3)
C2—H2	0.9500	C24—C25	1.370 (3)
C3—C21	1.462 (3)	C24—H24	0.9500
C3—H3	0.9500	C25—C26	1.420 (4)
C11—C12	1.400 (4)	C25—H25	0.9500
C11—C16	1.401 (3)	C26—C27	1.382 (3)
C12—C13	1.396 (3)	C27—C28	1.424 (3)
C12—H12	0.9500	C27—H27	0.9500
C13—C14	1.390 (4)	C28—C29	1.430 (3)
C13—H13	0.9500	C29—C30	1.370 (3)
C14—C15	1.395 (4)	C29—H29	0.9500
C14—H14	0.9500	C30—H30	0.9500
C15—C16	1.383 (3)	C31—H31A	0.9800
C15—H15	0.9500	C31—H31B	0.9800
C16—H16	0.9500	C31—H31C	0.9800
C26—O2—C31	117.66 (19)	C21—C22—H22	118.9
O1—C1—C2	120.8 (2)	C23—C22—H22	118.9
O1—C1—C11	119.5 (2)	C22—C23—C24	122.5 (2)
C2—C1—C11	119.8 (2)	C22—C23—C28	119.19 (18)
C3—C2—C1	119.2 (2)	C24—C23—C28	118.26 (18)
C3—C2—H2	120.4	C25—C24—C23	121.1 (2)
C1—C2—H2	120.4	C25—C24—H24	119.4
C2—C3—C21	128.4 (2)	C23—C24—H24	119.4
C2—C3—H3	115.8	C24—C25—C26	120.14 (19)
C21—C3—H3	115.8	C24—C25—H25	119.9
C12—C11—C16	119.0 (2)	C26—C25—H25	119.9
C12—C11—C1	122.9 (2)	O2—C26—C27	125.3 (2)
C16—C11—C1	118.0 (2)	O2—C26—C25	113.65 (19)
C13—C12—C11	119.8 (2)	C27—C26—C25	121.08 (19)
C13—C12—H12	120.1	C26—C27—C28	119.5 (2)
C11—C12—H12	120.1	C26—C27—H27	120.3
C14—C13—C12	120.5 (2)	C28—C27—H27	120.3
C14—C13—H13	119.7	C27—C28—C29	122.2 (2)
C12—C13—H13	119.7	C27—C28—C23	119.86 (18)
C13—C14—C15	119.7 (2)	C29—C28—C23	117.96 (19)
C13—C14—H14	120.2	C30—C29—C28	121.4 (2)
C15—C14—H14	120.2	C30—C29—H29	119.3
C16—C15—C14	120.0 (2)	C28—C29—H29	119.3
C16—C15—H15	120.0	C29—C30—C21	121.0 (2)
C14—C15—H15	120.0	C29—C30—H30	119.5
C15—C16—C11	120.8 (2)	C21—C30—H30	119.5
C15—C16—H16	119.6	O2—C31—H31A	109.5
C11—C16—H16	119.6	O2—C31—H31B	109.5
C22—C21—C30	118.14 (19)	H31A—C31—H31B	109.5
C22—C21—C3	119.1 (2)	O2—C31—H31C	109.5
C30—C21—C3	122.65 (19)	H31A—C31—H31C	109.5
C21—C22—C23	122.3 (2)	H31B—C31—H31C	109.5
O1—C1—C2—C3	−15.9 (4)	C22—C23—C24—C25	179.1 (2)
C11—C1—C2—C3	164.3 (2)	C28—C23—C24—C25	−1.1 (3)
C1—C2—C3—C21	177.3 (2)	C23—C24—C25—C26	−0.7 (3)
O1—C1—C11—C12	−156.2 (3)	C31—O2—C26—C27	−5.4 (3)
C2—C1—C11—C12	23.6 (3)	C31—O2—C26—C25	173.4 (2)
O1—C1—C11—C16	21.0 (3)	C24—C25—C26—O2	−178.3 (2)
C2—C1—C11—C16	−159.2 (2)	C24—C25—C26—C27	0.6 (3)
C16—C11—C12—C13	−2.6 (3)	O2—C26—C27—C28	−180.0 (2)
C1—C11—C12—C13	174.6 (2)	C25—C26—C27—C28	1.3 (3)
C11—C12—C13—C14	2.5 (3)	C26—C27—C28—C29	177.92 (19)
C12—C13—C14—C15	−0.1 (3)	C26—C27—C28—C23	−3.1 (3)
C13—C14—C15—C16	−2.2 (3)	C22—C23—C28—C27	−177.19 (19)
C14—C15—C16—C11	2.1 (3)	C24—C23—C28—C27	2.9 (3)
C12—C11—C16—C15	0.3 (3)	C22—C23—C28—C29	1.8 (3)
C1—C11—C16—C15	−177.0 (2)	C24—C23—C28—C29	−178.04 (18)
C2—C3—C21—C22	172.6 (2)	C27—C28—C29—C30	178.20 (19)
C2—C3—C21—C30	−10.4 (3)	C23—C28—C29—C30	−0.8 (3)
C30—C21—C22—C23	−1.7 (3)	C28—C29—C30—C21	−1.5 (3)
C3—C21—C22—C23	175.49 (18)	C22—C21—C30—C29	2.7 (3)
C21—C22—C23—C24	179.28 (19)	C3—C21—C30—C29	−174.32 (19)
C21—C22—C23—C28	−0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.95	2.44	2.798 (3)	102
C14—H14···O2^i	0.95	2.53	3.462 (3)	168

Symmetry code: (i) x, y−1, z.