3-(6-Meth­oxy-2-naphth­yl)-1-(2-naphth­yl)prop-2-en-1-one

The title compound, C₂₄H₁₈O₂, is a chalcone derivative The torsion angle between the mean planes of the two naphthalene groups is 54.41 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.036
• wR factor = 0.102
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

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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.

;

Crystal data

C24H18O2	F(000) = 712
Mr = 338.38	Dx = 1.339 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8060 reflections
a = 7.5270 (8) Å	θ = 2.2–25.4°
b = 5.9364 (4) Å	µ = 0.08 mm^−1
c = 37.576 (4) Å	T = 173 K
β = 92.046 (8)°	Plate, light yellow
V = 1677.9 (3) Å^3	0.42 × 0.37 × 0.13 mm
Z = 4

Data collection

STOE IPDS II two-circle- diffractometer	2455 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
ω scans	h = −8→8
9309 measured reflections	k = −7→7
2940 independent reflections	l = −44→44

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)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0683P)^2 + 0.0701P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2940 reflections	Δρmax = 0.21 e Å^−3
237 parameters	Δρmin = −0.15 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: 0.028 (3)

Special details

Experimental. ;

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	0.51277 (11)	0.70712 (15)	0.74829 (2)	0.0355 (2)
O2	0.28946 (13)	−0.18896 (15)	0.50713 (3)	0.0424 (3)
C1	0.34928 (15)	0.27999 (19)	0.59321 (3)	0.0275 (3)
C2	0.43030 (15)	0.4960 (2)	0.58887 (3)	0.0298 (3)
H2	0.4509	0.5507	0.5656	0.036*
C3	0.47834 (15)	0.62437 (19)	0.61782 (3)	0.0294 (3)
H3	0.5340	0.7659	0.6143	0.035*
C4	0.44688 (15)	0.55099 (19)	0.65302 (3)	0.0266 (3)
C5	0.35812 (14)	0.34154 (19)	0.65752 (3)	0.0265 (3)
C6	0.31485 (15)	0.20862 (19)	0.62715 (3)	0.0277 (3)
H6	0.2604	0.0659	0.6303	0.033*
C7	0.49996 (15)	0.67954 (19)	0.68340 (3)	0.0288 (3)
H7	0.5614	0.8179	0.6806	0.035*
C8	0.46249 (15)	0.6037 (2)	0.71677 (3)	0.0288 (3)
C9	0.36418 (16)	0.4032 (2)	0.72121 (3)	0.0320 (3)
H9	0.3321	0.3576	0.7444	0.038*
C10	0.31552 (16)	0.2754 (2)	0.69245 (3)	0.0310 (3)
H10	0.2518	0.1394	0.6958	0.037*
C11	0.62639 (19)	0.8993 (2)	0.74619 (4)	0.0403 (3)
H11A	0.7365	0.8564	0.7348	0.060*
H11B	0.6545	0.9561	0.7702	0.060*
H11C	0.5660	1.0173	0.7321	0.060*
C12	0.30577 (15)	0.1325 (2)	0.56291 (3)	0.0298 (3)
H12	0.2745	−0.0182	0.5684	0.036*
C13	0.30517 (16)	0.1859 (2)	0.52845 (3)	0.0323 (3)
H13	0.3295	0.3364	0.5215	0.039*
C14	0.26685 (16)	0.0126 (2)	0.50084 (3)	0.0324 (3)
C21	0.20126 (15)	0.0885 (2)	0.46481 (3)	0.0290 (3)
C22	0.11932 (16)	0.3026 (2)	0.45942 (4)	0.0329 (3)
H22	0.1093	0.4029	0.4789	0.039*
C23	0.05511 (16)	0.3647 (2)	0.42648 (4)	0.0330 (3)
H23	−0.0025	0.5062	0.4235	0.040*
C24	0.07268 (15)	0.22212 (19)	0.39657 (3)	0.0289 (3)
C25	0.15706 (15)	0.00758 (19)	0.40170 (3)	0.0268 (3)
C26	0.21698 (15)	−0.0545 (2)	0.43627 (3)	0.0287 (3)
H26	0.2695	−0.1985	0.4400	0.034*
C27	0.01404 (16)	0.2854 (2)	0.36175 (4)	0.0339 (3)
H27	−0.0422	0.4271	0.3580	0.041*
C28	0.03745 (17)	0.1452 (2)	0.33354 (4)	0.0375 (3)
H28	−0.0033	0.1899	0.3104	0.045*
C29	0.12191 (17)	−0.0664 (2)	0.33843 (4)	0.0366 (3)
H29	0.1382	−0.1621	0.3185	0.044*
C30	0.17987 (16)	−0.1333 (2)	0.37156 (3)	0.0314 (3)
H30	0.2361	−0.2757	0.3746	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0371 (5)	0.0385 (5)	0.0307 (5)	−0.0042 (4)	−0.0006 (4)	−0.0079 (4)
O2	0.0623 (7)	0.0321 (5)	0.0326 (6)	0.0032 (4)	0.0014 (4)	0.0009 (4)
C1	0.0252 (6)	0.0279 (6)	0.0294 (7)	0.0025 (5)	0.0001 (5)	0.0017 (5)
C2	0.0296 (6)	0.0313 (6)	0.0285 (7)	−0.0001 (5)	0.0022 (5)	0.0042 (5)
C3	0.0283 (6)	0.0260 (6)	0.0338 (7)	−0.0025 (5)	0.0012 (5)	0.0038 (5)
C4	0.0221 (5)	0.0259 (6)	0.0316 (7)	0.0020 (5)	0.0000 (5)	0.0015 (5)
C5	0.0225 (6)	0.0265 (6)	0.0303 (7)	0.0012 (4)	−0.0002 (5)	0.0013 (5)
C6	0.0268 (6)	0.0246 (6)	0.0317 (7)	−0.0013 (4)	−0.0001 (5)	0.0018 (5)
C7	0.0275 (6)	0.0245 (6)	0.0343 (7)	−0.0003 (5)	−0.0010 (5)	−0.0006 (5)
C8	0.0256 (6)	0.0305 (6)	0.0301 (7)	0.0029 (5)	−0.0013 (5)	−0.0043 (5)
C9	0.0304 (6)	0.0379 (7)	0.0278 (7)	−0.0026 (5)	0.0019 (5)	0.0016 (5)
C10	0.0313 (6)	0.0304 (6)	0.0313 (7)	−0.0050 (5)	0.0009 (5)	0.0025 (5)
C11	0.0503 (8)	0.0297 (7)	0.0401 (8)	−0.0039 (6)	−0.0108 (6)	−0.0038 (6)
C12	0.0287 (6)	0.0284 (6)	0.0324 (7)	0.0003 (5)	0.0016 (5)	−0.0006 (5)
C13	0.0345 (7)	0.0315 (7)	0.0309 (7)	−0.0023 (5)	0.0015 (5)	0.0003 (5)
C14	0.0340 (7)	0.0319 (7)	0.0317 (7)	−0.0017 (5)	0.0047 (5)	0.0002 (5)
C21	0.0269 (6)	0.0292 (6)	0.0311 (7)	−0.0034 (5)	0.0034 (5)	−0.0019 (5)
C22	0.0330 (7)	0.0309 (6)	0.0349 (8)	0.0012 (5)	0.0037 (5)	−0.0065 (5)
C23	0.0296 (6)	0.0269 (6)	0.0425 (8)	0.0034 (5)	0.0002 (5)	−0.0012 (5)
C24	0.0233 (6)	0.0280 (6)	0.0352 (7)	−0.0038 (5)	0.0000 (5)	0.0016 (5)
C25	0.0246 (6)	0.0252 (6)	0.0307 (7)	−0.0034 (4)	0.0016 (5)	0.0000 (5)
C26	0.0280 (6)	0.0241 (6)	0.0339 (7)	−0.0004 (5)	0.0021 (5)	0.0006 (5)
C27	0.0281 (6)	0.0318 (7)	0.0415 (8)	−0.0035 (5)	−0.0042 (5)	0.0066 (6)
C28	0.0356 (7)	0.0447 (7)	0.0317 (8)	−0.0096 (6)	−0.0044 (6)	0.0075 (6)
C29	0.0401 (7)	0.0400 (7)	0.0297 (7)	−0.0078 (6)	0.0025 (5)	−0.0032 (6)
C30	0.0325 (6)	0.0287 (6)	0.0331 (7)	−0.0030 (5)	0.0025 (5)	−0.0013 (5)

Geometric parameters (Å, º)

O1—C8	1.3749 (15)	C12—C13	1.3332 (19)
O1—C11	1.4299 (16)	C12—H12	0.9500
O2—C14	1.2301 (15)	C13—C14	1.4821 (18)
C1—C6	1.3774 (18)	C13—H13	0.9500
C1—C2	1.4318 (17)	C14—C21	1.4941 (18)
C1—C12	1.4639 (18)	C21—C26	1.3759 (17)
C2—C3	1.3663 (18)	C21—C22	1.4240 (17)
C2—H2	0.9500	C22—C23	1.3635 (19)
C3—C4	1.4205 (18)	C22—H22	0.9500
C3—H3	0.9500	C23—C24	1.4168 (18)
C4—C7	1.4185 (18)	C23—H23	0.9500
C4—C5	1.4244 (16)	C24—C27	1.4167 (19)
C5—C6	1.4157 (17)	C24—C25	1.4331 (16)
C5—C10	1.4178 (17)	C25—C26	1.4091 (18)
C6—H6	0.9500	C25—C30	1.4234 (17)
C7—C8	1.3711 (18)	C26—H26	0.9500
C7—H7	0.9500	C27—C28	1.3639 (19)
C8—C9	1.4149 (17)	C27—H27	0.9500
C9—C10	1.3598 (18)	C28—C29	1.4172 (19)
C9—H9	0.9500	C28—H28	0.9500
C10—H10	0.9500	C29—C30	1.3635 (19)
C11—H11A	0.9800	C29—H29	0.9500
C11—H11B	0.9800	C30—H30	0.9500
C11—H11C	0.9800
C8—O1—C11	117.10 (10)	C13—C12—H12	116.3
C6—C1—C2	118.41 (11)	C1—C12—H12	116.3
C6—C1—C12	119.46 (11)	C12—C13—C14	120.57 (12)
C2—C1—C12	122.11 (11)	C12—C13—H13	119.7
C3—C2—C1	120.71 (11)	C14—C13—H13	119.7
C3—C2—H2	119.6	O2—C14—C13	121.24 (12)
C1—C2—H2	119.6	O2—C14—C21	120.42 (11)
C2—C3—C4	121.48 (11)	C13—C14—C21	118.33 (11)
C2—C3—H3	119.3	C26—C21—C22	119.26 (11)
C4—C3—H3	119.3	C26—C21—C14	119.03 (11)
C7—C4—C3	122.19 (11)	C22—C21—C14	121.69 (11)
C7—C4—C5	119.61 (11)	C23—C22—C21	120.53 (12)
C3—C4—C5	118.20 (11)	C23—C22—H22	119.7
C6—C5—C10	122.60 (11)	C21—C22—H22	119.7
C6—C5—C4	119.10 (11)	C22—C23—C24	121.23 (11)
C10—C5—C4	118.30 (11)	C22—C23—H23	119.4
C1—C6—C5	121.97 (11)	C24—C23—H23	119.4
C1—C6—H6	119.0	C27—C24—C23	122.64 (11)
C5—C6—H6	119.0	C27—C24—C25	118.81 (11)
C8—C7—C4	119.87 (11)	C23—C24—C25	118.53 (11)
C8—C7—H7	120.1	C26—C25—C30	122.42 (11)
C4—C7—H7	120.1	C26—C25—C24	118.83 (11)
C7—C8—O1	125.59 (11)	C30—C25—C24	118.74 (11)
C7—C8—C9	120.64 (11)	C21—C26—C25	121.56 (11)
O1—C8—C9	113.77 (11)	C21—C26—H26	119.2
C10—C9—C8	120.18 (12)	C25—C26—H26	119.2
C10—C9—H9	119.9	C28—C27—C24	120.75 (12)
C8—C9—H9	119.9	C28—C27—H27	119.6
C9—C10—C5	121.20 (11)	C24—C27—H27	119.6
C9—C10—H10	119.4	C27—C28—C29	120.67 (13)
C5—C10—H10	119.4	C27—C28—H28	119.7
O1—C11—H11A	109.5	C29—C28—H28	119.7
O1—C11—H11B	109.5	C30—C29—C28	120.26 (12)
H11A—C11—H11B	109.5	C30—C29—H29	119.9
O1—C11—H11C	109.5	C28—C29—H29	119.9
H11A—C11—H11C	109.5	C29—C30—C25	120.77 (12)
H11B—C11—H11C	109.5	C29—C30—H30	119.6
C13—C12—C1	127.31 (12)	C25—C30—H30	119.6
C6—C1—C2—C3	2.43 (17)	C12—C13—C14—O2	−23.05 (19)
C12—C1—C2—C3	−176.32 (11)	C12—C13—C14—C21	157.51 (11)
C1—C2—C3—C4	−1.23 (18)	O2—C14—C21—C26	−19.40 (18)
C2—C3—C4—C7	178.37 (11)	C13—C14—C21—C26	160.04 (11)
C2—C3—C4—C5	−1.96 (17)	O2—C14—C21—C22	159.12 (12)
C7—C4—C5—C6	−176.42 (10)	C13—C14—C21—C22	−21.44 (17)
C3—C4—C5—C6	3.90 (16)	C26—C21—C22—C23	0.78 (18)
C7—C4—C5—C10	4.00 (16)	C14—C21—C22—C23	−177.74 (11)
C3—C4—C5—C10	−175.67 (11)	C21—C22—C23—C24	−1.97 (19)
C2—C1—C6—C5	−0.39 (17)	C22—C23—C24—C27	−177.33 (11)
C12—C1—C6—C5	178.39 (10)	C22—C23—C24—C25	1.14 (18)
C10—C5—C6—C1	176.78 (11)	C27—C24—C25—C26	179.38 (10)
C4—C5—C6—C1	−2.78 (17)	C23—C24—C25—C26	0.86 (16)
C3—C4—C7—C8	178.39 (11)	C27—C24—C25—C30	0.41 (16)
C5—C4—C7—C8	−1.28 (17)	C23—C24—C25—C30	−178.11 (11)
C4—C7—C8—O1	177.16 (10)	C22—C21—C26—C25	1.26 (17)
C4—C7—C8—C9	−2.86 (17)	C14—C21—C26—C25	179.82 (10)
C11—O1—C8—C7	−5.62 (17)	C30—C25—C26—C21	176.87 (11)
C11—O1—C8—C9	174.40 (10)	C24—C25—C26—C21	−2.06 (17)
C7—C8—C9—C10	4.25 (18)	C23—C24—C27—C28	178.39 (11)
O1—C8—C9—C10	−175.76 (11)	C25—C24—C27—C28	−0.07 (18)
C8—C9—C10—C5	−1.39 (19)	C24—C27—C28—C29	−0.36 (19)
C6—C5—C10—C9	177.76 (11)	C27—C28—C29—C30	0.47 (19)
C4—C5—C10—C9	−2.68 (17)	C28—C29—C30—C25	−0.12 (19)
C6—C1—C12—C13	169.25 (12)	C26—C25—C30—C29	−179.25 (11)
C2—C1—C12—C13	−12.01 (19)	C24—C25—C30—C29	−0.32 (17)
C1—C12—C13—C14	176.77 (11)