(2,7-Dimeth-oxy-naphthalen-1-yl)(4-meth-oxy-phen-yl)methanone.

In the mol-ecule of the title compound, C20H18O4, the dihedral angle between the naphthalene ring system and the benzene ring is 81.74 (5)°. An inter-molecular C-H⋯O inter-action is formed between an H atom at the 6-position of the naphthalene ring and the O atom of the meth-oxy group at the 7-position.

Related literature

For formation reactions of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene deriv­atives, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Nakaema et al. (2008 ▶); Hijikata et al. (2010 ▶); Kato et al. (2010 ▶); Tsumuki et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C20H18O4

M = 322.34

Monoclinic,

a = 14.9638 (2) Å

b = 7.9191 (1) Å

c = 13.6394 (2) Å

β = 92.56°

V = 1614.64 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.75 mm−1

T = 193 K

0.60 × 0.40 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.662, T max = 0.806

27665 measured reflections

2957 independent reflections

2701 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.05

2957 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.18 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2010 ▶); program(s) used to solve structure: Il Milione (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813003218/pk2464sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003218/pk2464Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003218/pk2464Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H18O4	F(000) = 680
Mr = 322.34	Dx = 1.326 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 25377 reflections
a = 14.9638 (2) Å	θ = 3.0–68.2°
b = 7.9191 (1) Å	µ = 0.75 mm−1
c = 13.6394 (2) Å	T = 193 K
β = 92.56°	Block, colorless
V = 1614.64 (4) Å3	0.60 × 0.40 × 0.30 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2957 independent reflections
Radiation source: fine-focus sealed tube	2701 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.0°
ω scans	h = −17→18
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −9→9
Tmin = 0.662, Tmax = 0.806	l = −16→16
27665 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0622P)2 + 0.323P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2957 reflections	Δρmax = 0.24 e Å−3
221 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0093 (6)

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.

	x	y	z	Uiso*/Ueq
O1	0.34025 (6)	−0.17441 (11)	0.36039 (7)	0.0431 (3)
O2	0.26300 (6)	0.04715 (12)	0.55470 (6)	0.0428 (3)
O3	0.12880 (6)	−0.05902 (13)	0.04035 (7)	0.0463 (3)
O4	0.58557 (5)	0.47580 (11)	0.37408 (7)	0.0392 (2)
C1	0.22392 (8)	0.02329 (15)	0.38741 (9)	0.0324 (3)
C2	0.19845 (8)	0.06572 (15)	0.48029 (9)	0.0355 (3)
C3	0.11163 (8)	0.12450 (17)	0.49646 (10)	0.0403 (3)
H3	0.0950	0.1532	0.5608	0.048*
C4	0.05162 (8)	0.13973 (17)	0.41872 (10)	0.0412 (3)
H4	−0.0063	0.1833	0.4294	0.049*
C5	0.01000 (8)	0.10274 (18)	0.24246 (10)	0.0423 (3)
H5	−0.0480	0.1466	0.2526	0.051*
C6	0.03049 (8)	0.05121 (18)	0.15138 (10)	0.0430 (3)
H6	−0.0132	0.0565	0.0988	0.052*
C7	0.11745 (8)	−0.01061 (17)	0.13501 (9)	0.0373 (3)
C8	0.18197 (8)	−0.01881 (15)	0.20971 (9)	0.0342 (3)
H8	0.2404	−0.0578	0.1970	0.041*
C9	0.16091 (8)	0.03151 (15)	0.30639 (9)	0.0325 (3)
C10	0.07321 (8)	0.09269 (16)	0.32321 (9)	0.0364 (3)
C11	0.31989 (8)	−0.02724 (15)	0.37353 (8)	0.0318 (3)
C12	0.38717 (7)	0.11016 (15)	0.37531 (8)	0.0294 (3)
C13	0.36306 (7)	0.28000 (15)	0.36920 (8)	0.0311 (3)
H13	0.3015	0.3094	0.3664	0.037*
C14	0.42667 (8)	0.40714 (15)	0.36708 (8)	0.0317 (3)
H14	0.4090	0.5221	0.3614	0.038*
C15	0.51697 (7)	0.36349 (15)	0.37345 (8)	0.0311 (3)
C16	0.54233 (7)	0.19433 (16)	0.38133 (9)	0.0348 (3)
H16	0.6039	0.1652	0.3868	0.042*
C17	0.47838 (8)	0.06988 (15)	0.38119 (9)	0.0333 (3)
H17	0.4963	−0.0451	0.3851	0.040*
C18	0.23465 (11)	0.0506 (2)	0.65301 (10)	0.0510 (4)
H18A	0.1872	−0.0331	0.6605	0.061*
H18B	0.2118	0.1633	0.6679	0.061*
H18C	0.2854	0.0239	0.6982	0.061*
C19	0.21651 (9)	−0.1007 (2)	0.01257 (10)	0.0474 (3)
H19A	0.2387	−0.1976	0.0511	0.057*
H19B	0.2562	−0.0038	0.0248	0.057*
H19C	0.2151	−0.1293	−0.0574	0.057*
C20	0.56375 (9)	0.65140 (16)	0.37488 (9)	0.0381 (3)
H20A	0.6189	0.7181	0.3815	0.046*
H20B	0.5263	0.6754	0.4303	0.046*
H20C	0.5311	0.6812	0.3134	0.046*

	U11	U22	U33	U12	U13	U23
O1	0.0377 (5)	0.0318 (5)	0.0599 (6)	0.0008 (4)	0.0037 (4)	−0.0008 (4)
O2	0.0388 (5)	0.0573 (6)	0.0324 (5)	−0.0005 (4)	0.0015 (4)	−0.0039 (4)
O3	0.0376 (5)	0.0627 (6)	0.0380 (5)	0.0012 (4)	−0.0039 (4)	−0.0055 (4)
O4	0.0325 (4)	0.0321 (5)	0.0529 (5)	−0.0025 (3)	0.0004 (4)	0.0000 (4)
C1	0.0305 (6)	0.0302 (6)	0.0367 (6)	−0.0026 (5)	0.0038 (5)	0.0014 (5)
C2	0.0346 (6)	0.0349 (7)	0.0372 (6)	−0.0039 (5)	0.0023 (5)	−0.0005 (5)
C3	0.0399 (7)	0.0416 (7)	0.0403 (7)	−0.0006 (5)	0.0102 (5)	−0.0040 (5)
C4	0.0333 (6)	0.0401 (7)	0.0510 (7)	0.0027 (5)	0.0099 (5)	0.0013 (6)
C5	0.0283 (6)	0.0479 (8)	0.0506 (7)	0.0013 (5)	0.0022 (5)	0.0041 (6)
C6	0.0323 (6)	0.0517 (8)	0.0446 (7)	−0.0013 (5)	−0.0045 (5)	0.0040 (6)
C7	0.0348 (6)	0.0389 (7)	0.0380 (6)	−0.0036 (5)	−0.0003 (5)	0.0011 (5)
C8	0.0292 (6)	0.0339 (6)	0.0396 (7)	−0.0014 (5)	0.0021 (5)	0.0011 (5)
C9	0.0302 (6)	0.0288 (6)	0.0385 (6)	−0.0028 (4)	0.0028 (5)	0.0028 (5)
C10	0.0303 (6)	0.0351 (7)	0.0442 (7)	−0.0013 (5)	0.0046 (5)	0.0028 (5)
C11	0.0328 (6)	0.0345 (7)	0.0281 (6)	0.0024 (5)	0.0002 (4)	0.0020 (5)
C12	0.0306 (6)	0.0310 (6)	0.0264 (5)	0.0016 (4)	0.0009 (4)	0.0011 (4)
C13	0.0285 (5)	0.0350 (6)	0.0298 (5)	0.0042 (5)	0.0009 (4)	0.0014 (5)
C14	0.0351 (6)	0.0294 (6)	0.0306 (6)	0.0039 (5)	0.0008 (4)	0.0010 (5)
C15	0.0314 (6)	0.0329 (6)	0.0289 (5)	−0.0007 (5)	0.0008 (4)	−0.0010 (5)
C16	0.0271 (6)	0.0351 (7)	0.0419 (7)	0.0044 (5)	0.0000 (5)	0.0002 (5)
C17	0.0339 (6)	0.0294 (6)	0.0365 (6)	0.0050 (5)	0.0010 (5)	0.0015 (5)
C18	0.0548 (8)	0.0635 (10)	0.0348 (7)	0.0035 (7)	0.0044 (6)	−0.0049 (6)
C19	0.0430 (7)	0.0600 (9)	0.0393 (7)	0.0039 (6)	0.0021 (6)	−0.0061 (6)
C20	0.0441 (7)	0.0321 (7)	0.0379 (6)	−0.0042 (5)	0.0004 (5)	0.0006 (5)

O1—C11	1.2199 (15)	C8—H8	0.9500
O2—C2	1.3773 (15)	C9—C10	1.4270 (17)
O2—C18	1.4245 (16)	C11—C12	1.4819 (16)
O3—C7	1.3648 (15)	C12—C13	1.3941 (17)
O3—C19	1.4210 (16)	C12—C17	1.4004 (16)
O4—C15	1.3580 (14)	C13—C14	1.3867 (17)
O4—C20	1.4286 (15)	C13—H13	0.9500
C1—C2	1.3807 (17)	C14—C15	1.3936 (16)
C1—C9	1.4216 (17)	C14—H14	0.9500
C1—C11	1.5108 (16)	C15—C16	1.3951 (17)
C2—C3	1.4066 (17)	C16—C17	1.3736 (17)
C3—C4	1.3638 (19)	C16—H16	0.9500
C3—H3	0.9500	C17—H17	0.9500
C4—C10	1.4063 (18)	C18—H18A	0.9800
C4—H4	0.9500	C18—H18B	0.9800
C5—C6	1.3556 (19)	C18—H18C	0.9800
C5—C10	1.4217 (18)	C19—H19A	0.9800
C5—H5	0.9500	C19—H19B	0.9800
C6—C7	1.4172 (18)	C19—H19C	0.9800
C6—H6	0.9500	C20—H20A	0.9800
C7—C8	1.3735 (17)	C20—H20B	0.9800
C8—C9	1.4262 (17)	C20—H20C	0.9800
C2—O2—C18	117.58 (10)	C13—C12—C17	118.17 (11)
C7—O3—C19	118.23 (10)	C13—C12—C11	122.25 (10)
C15—O4—C20	117.68 (9)	C17—C12—C11	119.57 (11)
C2—C1—C9	120.09 (11)	C14—C13—C12	121.71 (10)
C2—C1—C11	118.84 (10)	C14—C13—H13	119.1
C9—C1—C11	121.05 (10)	C12—C13—H13	119.1
O2—C2—C1	115.90 (10)	C13—C14—C15	118.89 (11)
O2—C2—C3	122.82 (11)	C13—C14—H14	120.6
C1—C2—C3	121.28 (12)	C15—C14—H14	120.6
C4—C3—C2	119.21 (12)	O4—C15—C14	124.64 (11)
C4—C3—H3	120.4	O4—C15—C16	115.18 (10)
C2—C3—H3	120.4	C14—C15—C16	120.17 (11)
C3—C4—C10	121.75 (11)	C17—C16—C15	120.12 (11)
C3—C4—H4	119.1	C17—C16—H16	119.9
C10—C4—H4	119.1	C15—C16—H16	119.9
C6—C5—C10	121.54 (12)	C16—C17—C12	120.91 (11)
C6—C5—H5	119.2	C16—C17—H17	119.5
C10—C5—H5	119.2	C12—C17—H17	119.5
C5—C6—C7	119.69 (12)	O2—C18—H18A	109.5
C5—C6—H6	120.2	O2—C18—H18B	109.5
C7—C6—H6	120.2	H18A—C18—H18B	109.5
O3—C7—C8	125.13 (11)	O2—C18—H18C	109.5
O3—C7—C6	113.58 (11)	H18A—C18—H18C	109.5
C8—C7—C6	121.29 (12)	H18B—C18—H18C	109.5
C7—C8—C9	119.71 (11)	O3—C19—H19A	109.5
C7—C8—H8	120.1	O3—C19—H19B	109.5
C9—C8—H8	120.1	H19A—C19—H19B	109.5
C1—C9—C8	122.65 (11)	O3—C19—H19C	109.5
C1—C9—C10	118.25 (11)	H19A—C19—H19C	109.5
C8—C9—C10	119.10 (11)	H19B—C19—H19C	109.5
C4—C10—C5	122.03 (11)	O4—C20—H20A	109.5
C4—C10—C9	119.33 (12)	O4—C20—H20B	109.5
C5—C10—C9	118.64 (11)	H20A—C20—H20B	109.5
O1—C11—C12	122.00 (11)	O4—C20—H20C	109.5
O1—C11—C1	121.09 (11)	H20A—C20—H20C	109.5
C12—C11—C1	116.90 (10)	H20B—C20—H20C	109.5
C18—O2—C2—C1	−165.55 (12)	C6—C5—C10—C9	1.9 (2)
C18—O2—C2—C3	14.60 (18)	C1—C9—C10—C4	−1.07 (17)
C9—C1—C2—O2	177.39 (10)	C8—C9—C10—C4	178.91 (11)
C11—C1—C2—O2	−4.15 (17)	C1—C9—C10—C5	179.46 (11)
C9—C1—C2—C3	−2.75 (19)	C8—C9—C10—C5	−0.56 (18)
C11—C1—C2—C3	175.71 (11)	C2—C1—C11—O1	105.40 (14)
O2—C2—C3—C4	179.84 (12)	C9—C1—C11—O1	−76.15 (15)
C1—C2—C3—C4	0.0 (2)	C2—C1—C11—C12	−75.42 (14)
C2—C3—C4—C10	2.2 (2)	C9—C1—C11—C12	103.03 (13)
C10—C5—C6—C7	−1.5 (2)	O1—C11—C12—C13	165.98 (11)
C19—O3—C7—C8	−8.7 (2)	C1—C11—C12—C13	−13.19 (16)
C19—O3—C7—C6	171.37 (12)	O1—C11—C12—C17	−12.62 (17)
C5—C6—C7—O3	179.62 (12)	C1—C11—C12—C17	168.21 (10)
C5—C6—C7—C8	−0.3 (2)	C17—C12—C13—C14	1.17 (16)
O3—C7—C8—C9	−178.27 (12)	C11—C12—C13—C14	−177.45 (10)
C6—C7—C8—C9	1.65 (19)	C12—C13—C14—C15	−1.44 (17)
C2—C1—C9—C8	−176.75 (11)	C20—O4—C15—C14	4.39 (16)
C11—C1—C9—C8	4.82 (18)	C20—O4—C15—C16	−174.64 (10)
C2—C1—C9—C10	3.23 (17)	C13—C14—C15—O4	−178.69 (10)
C11—C1—C9—C10	−175.20 (11)	C13—C14—C15—C16	0.29 (17)
C7—C8—C9—C1	178.80 (11)	O4—C15—C16—C17	−179.82 (10)
C7—C8—C9—C10	−1.18 (18)	C14—C15—C16—C17	1.10 (17)
C3—C4—C10—C5	177.77 (13)	C15—C16—C17—C12	−1.38 (18)
C3—C4—C10—C9	−1.68 (19)	C13—C12—C17—C16	0.26 (17)
C6—C5—C10—C4	−177.53 (13)	C11—C12—C17—C16	178.92 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3i	0.95	2.51	3.4592 (16)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3i	0.95	2.51	3.4592 (16)	178

Symmetry code: (i) .