(3,6-Dimeth-oxy-naphthalen-2-yl)(naphthalen-2-yl)methanone.

In the title compound, C(23)H(18)O(3), the dihedral angle between the two naphthalene ring systems is 78.02 (3)°. The bridging carbonyl C-C(=O)-C plane makes a dihedral angle of 70.56 (5)° with the naphthalene ring system in the 2,7-dimeth-oxy-naphthalene moiety and a dihedral angle of 11.53 (5)° with the naphthalene ring system in the naphthoyl group. In the crystal, adjacent mol-ecules are linked via C-H⋯π inter-actions, forming chains along [010].

Related literature

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

Experimental

Crystal data

C23H18O3

M = 342.37

Monoclinic,

a = 13.4683 (9) Å

b = 8.9062 (5) Å

c = 14.7110 (8) Å

β = 105.646 (2)°

V = 1699.23 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 193 K

0.60 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.941, T max = 0.983

26536 measured reflections

3863 independent reflections

3436 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.109

S = 1.06

3863 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.18 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812034186/su2487sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034186/su2487Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034186/su2487Isup3.cml

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

C23H18O3	F(000) = 720
Mr = 342.37	Dx = 1.338 Mg m−3
Monoclinic, P21/c	Melting point = 444.0–445.0 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71075 Å
a = 13.4683 (9) Å	Cell parameters from 20190 reflections
b = 8.9062 (5) Å	θ = 3.1–27.4°
c = 14.7110 (8) Å	µ = 0.09 mm−1
β = 105.646 (2)°	T = 193 K
V = 1699.23 (17) Å3	Block, colourless
Z = 4	0.60 × 0.30 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	3863 independent reflections
Radiation source: rotating anode	3436 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 10.00 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −17→17
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −11→11
Tmin = 0.941, Tmax = 0.983	l = −19→18
26536 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) = 0.109	w = 1/[σ2(Fo2) + (0.0609P)2 + 0.3821P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3863 reflections	Δρmax = 0.31 e Å−3
238 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: 0.0154 (19)

Experimental. Spectroscopic data for the title compound: 1H NMR δ (300 MHz, CDCl3): 3.83 (3H, s), 3.96 (3H, s), 7.07 (1H, dd, J = 2.4, 9.0 Hz), 7.14 (1H, d, J = 2.4 Hz), 7.18 (1H, s), 7.51 (1H, dt, J = 1.2, 7.5 Hz), 7.60 (1H, dt, J = 1.2, 7.5 Hz), 7.71 (1H, d, J = 9.0 Hz), 7.84–7.92 (4H, m), 8.02 (1H, dd, J = 1.2, 9.0 Hz), 8.26 (1H,d, J = 1.2 Hz) p.p.m. 13C NMR δ (125 MHz, CDCl3): 195.97, 159.32, 155.89, 137.11, 135.55, 135.46, 132.39, 132.19, 130.03, 130.01, 129.59, 128.35, 128.05, 128.02, 127.73, 126.52, 125.17, 123.17, 117.02, 105.43, 105.04, 55.56, 55.32 p.p.m. IR (KBr, cm-1): 1666, 1630, 1459, 1226, 1191 HRMS (m/z): [M+H]+ calcd. for C23H19O3, 343.1334, found, 343.1344.

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.

	x	y	z	Uiso*/Ueq
O1	0.31909 (7)	0.44270 (11)	0.02517 (6)	0.0449 (2)
O2	0.21312 (6)	0.25562 (9)	0.18816 (5)	0.03164 (19)
O3	0.66735 (6)	0.30077 (10)	0.59573 (6)	0.0396 (2)
C1	0.35816 (8)	0.26610 (11)	0.32895 (7)	0.0256 (2)
H1	0.3284	0.1931	0.3606	0.031*
C2	0.30615 (7)	0.31204 (11)	0.23965 (7)	0.0248 (2)
C3	0.34880 (8)	0.42318 (11)	0.19167 (7)	0.0252 (2)
C4	0.44353 (8)	0.48307 (12)	0.23457 (7)	0.0282 (2)
H4	0.4720	0.5567	0.2022	0.034*
C5	0.50006 (8)	0.43750 (11)	0.32631 (7)	0.0270 (2)
C6	0.59859 (9)	0.49671 (14)	0.37265 (8)	0.0363 (3)
H6	0.6283	0.5713	0.3420	0.044*
C7	0.65131 (9)	0.44839 (15)	0.46046 (9)	0.0390 (3)
H7	0.7175	0.4886	0.4900	0.047*
C8	0.60763 (8)	0.33873 (13)	0.50744 (7)	0.0311 (2)
C9	0.51225 (8)	0.27940 (12)	0.46576 (7)	0.0278 (2)
H9	0.4834	0.2062	0.4981	0.033*
C10	0.45652 (7)	0.32767 (11)	0.37402 (7)	0.0244 (2)
C11	0.28960 (8)	0.47414 (12)	0.09415 (7)	0.0279 (2)
C12	0.19693 (8)	0.56988 (11)	0.08637 (7)	0.0263 (2)
C13	0.17608 (7)	0.62890 (11)	0.16571 (6)	0.0236 (2)
H13	0.2198	0.6049	0.2262	0.028*
C14	0.09043 (7)	0.72487 (11)	0.15864 (7)	0.0233 (2)
C15	0.06908 (8)	0.78952 (11)	0.23953 (7)	0.0260 (2)
H15	0.1131	0.7686	0.3004	0.031*
C16	−0.01430 (8)	0.88170 (12)	0.23057 (7)	0.0300 (2)
H16	−0.0272	0.9255	0.2851	0.036*
C17	−0.08113 (9)	0.91196 (14)	0.14072 (8)	0.0358 (3)
H17	−0.1393	0.9751	0.1352	0.043*
C18	−0.06276 (9)	0.85107 (15)	0.06142 (8)	0.0408 (3)
H18	−0.1086	0.8719	0.0013	0.049*
C19	0.02400 (9)	0.75705 (13)	0.06789 (7)	0.0318 (2)
C20	0.04710 (10)	0.69372 (16)	−0.01265 (8)	0.0444 (3)
H20	0.0031	0.7144	−0.0736	0.053*
C21	0.13096 (10)	0.60409 (15)	−0.00430 (7)	0.0390 (3)
H21	0.1455	0.5642	−0.0592	0.047*
C22	0.17610 (8)	0.12457 (12)	0.22435 (8)	0.0334 (2)
H22A	0.1108	0.0929	0.1808	0.040*
H22B	0.1652	0.1471	0.2861	0.040*
H22C	0.2269	0.0437	0.2310	0.040*
C23	0.62408 (10)	0.19186 (14)	0.64517 (9)	0.0407 (3)
H23A	0.6707	0.1764	0.7083	0.049*
H23B	0.6147	0.0968	0.6103	0.049*
H23C	0.5572	0.2276	0.6508	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0548 (5)	0.0553 (5)	0.0303 (4)	0.0209 (4)	0.0210 (4)	0.0045 (4)
O2	0.0279 (4)	0.0306 (4)	0.0328 (4)	−0.0027 (3)	0.0019 (3)	0.0078 (3)
O3	0.0329 (4)	0.0456 (5)	0.0342 (4)	−0.0046 (4)	−0.0015 (3)	0.0070 (4)
C1	0.0263 (5)	0.0232 (4)	0.0286 (5)	0.0005 (4)	0.0095 (4)	0.0039 (4)
C2	0.0232 (5)	0.0233 (5)	0.0286 (5)	0.0027 (4)	0.0082 (4)	0.0008 (4)
C3	0.0278 (5)	0.0241 (5)	0.0262 (5)	0.0057 (4)	0.0114 (4)	0.0029 (4)
C4	0.0308 (5)	0.0265 (5)	0.0310 (5)	0.0010 (4)	0.0146 (4)	0.0051 (4)
C5	0.0264 (5)	0.0268 (5)	0.0302 (5)	0.0006 (4)	0.0117 (4)	0.0014 (4)
C6	0.0312 (5)	0.0400 (6)	0.0391 (6)	−0.0085 (5)	0.0120 (5)	0.0065 (5)
C7	0.0279 (5)	0.0464 (7)	0.0404 (6)	−0.0097 (5)	0.0051 (5)	0.0026 (5)
C8	0.0284 (5)	0.0337 (5)	0.0297 (5)	0.0013 (4)	0.0054 (4)	0.0017 (4)
C9	0.0282 (5)	0.0264 (5)	0.0289 (5)	0.0010 (4)	0.0082 (4)	0.0033 (4)
C10	0.0246 (5)	0.0226 (4)	0.0273 (5)	0.0029 (4)	0.0093 (4)	0.0007 (4)
C11	0.0337 (5)	0.0268 (5)	0.0256 (5)	0.0034 (4)	0.0121 (4)	0.0025 (4)
C12	0.0311 (5)	0.0266 (5)	0.0222 (5)	0.0033 (4)	0.0086 (4)	0.0031 (4)
C13	0.0263 (5)	0.0241 (5)	0.0199 (4)	−0.0001 (4)	0.0053 (3)	0.0024 (3)
C14	0.0260 (5)	0.0235 (4)	0.0203 (4)	−0.0009 (4)	0.0061 (4)	0.0013 (3)
C15	0.0300 (5)	0.0269 (5)	0.0215 (4)	0.0002 (4)	0.0075 (4)	0.0010 (4)
C16	0.0343 (5)	0.0304 (5)	0.0280 (5)	0.0021 (4)	0.0131 (4)	−0.0007 (4)
C17	0.0318 (5)	0.0402 (6)	0.0354 (6)	0.0113 (5)	0.0091 (4)	0.0022 (5)
C18	0.0384 (6)	0.0526 (7)	0.0273 (5)	0.0175 (5)	0.0019 (4)	0.0023 (5)
C19	0.0339 (6)	0.0377 (6)	0.0221 (5)	0.0085 (4)	0.0045 (4)	0.0017 (4)
C20	0.0511 (7)	0.0594 (8)	0.0182 (5)	0.0231 (6)	0.0018 (5)	0.0016 (5)
C21	0.0497 (7)	0.0483 (7)	0.0191 (5)	0.0172 (6)	0.0092 (5)	0.0007 (4)
C22	0.0270 (5)	0.0302 (5)	0.0404 (6)	−0.0029 (4)	0.0049 (4)	0.0066 (4)
C23	0.0456 (7)	0.0363 (6)	0.0335 (6)	−0.0015 (5)	−0.0009 (5)	0.0082 (5)

O1—C11	1.2179 (13)	C12—C21	1.4221 (14)
O2—C2	1.3726 (12)	C13—C14	1.4168 (14)
O2—C22	1.4274 (13)	C13—H13	0.9500
O3—C8	1.3729 (13)	C14—C15	1.4195 (13)
O3—C23	1.4276 (15)	C14—C19	1.4215 (14)
C1—C2	1.3739 (14)	C15—C16	1.3684 (14)
C1—C10	1.4219 (14)	C15—H15	0.9500
C1—H1	0.9500	C16—C17	1.4101 (15)
C2—C3	1.4235 (14)	C16—H16	0.9500
C3—C4	1.3698 (15)	C17—C18	1.3683 (16)
C3—C11	1.5109 (14)	C17—H17	0.9500
C4—C5	1.4183 (15)	C18—C19	1.4198 (15)
C4—H4	0.9500	C18—H18	0.9500
C5—C10	1.4195 (14)	C19—C20	1.4204 (15)
C5—C6	1.4198 (15)	C20—C21	1.3613 (17)
C6—C7	1.3651 (17)	C20—H20	0.9500
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.4131 (16)	C22—H22A	0.9800
C7—H7	0.9500	C22—H22B	0.9800
C8—C9	1.3713 (15)	C22—H22C	0.9800
C9—C10	1.4223 (14)	C23—H23A	0.9800
C9—H9	0.9500	C23—H23B	0.9800
C11—C12	1.4903 (14)	C23—H23C	0.9800
C12—C13	1.3762 (13)
C2—O2—C22	116.88 (8)	C12—C13—H13	119.5
C8—O3—C23	115.71 (9)	C14—C13—H13	119.5
C2—C1—C10	120.12 (9)	C13—C14—C15	121.89 (9)
C2—C1—H1	119.9	C13—C14—C19	118.97 (9)
C10—C1—H1	119.9	C15—C14—C19	119.15 (9)
O2—C2—C1	124.94 (9)	C16—C15—C14	120.61 (9)
O2—C2—C3	114.29 (9)	C16—C15—H15	119.7
C1—C2—C3	120.75 (9)	C14—C15—H15	119.7
C4—C3—C2	119.51 (9)	C15—C16—C17	120.32 (10)
C4—C3—C11	120.52 (9)	C15—C16—H16	119.8
C2—C3—C11	119.97 (9)	C17—C16—H16	119.8
C3—C4—C5	121.41 (9)	C18—C17—C16	120.46 (10)
C3—C4—H4	119.3	C18—C17—H17	119.8
C5—C4—H4	119.3	C16—C17—H17	119.8
C4—C5—C10	118.71 (9)	C17—C18—C19	120.75 (10)
C4—C5—C6	122.88 (10)	C17—C18—H18	119.6
C10—C5—C6	118.41 (9)	C19—C18—H18	119.6
C7—C6—C5	121.17 (10)	C18—C19—C20	122.66 (10)
C7—C6—H6	119.4	C18—C19—C14	118.69 (10)
C5—C6—H6	119.4	C20—C19—C14	118.65 (10)
C6—C7—C8	120.11 (10)	C21—C20—C19	121.38 (10)
C6—C7—H7	119.9	C21—C20—H20	119.3
C8—C7—H7	119.9	C19—C20—H20	119.3
C9—C8—O3	124.56 (10)	C20—C21—C12	120.23 (10)
C9—C8—C7	120.73 (10)	C20—C21—H21	119.9
O3—C8—C7	114.70 (10)	C12—C21—H21	119.9
C8—C9—C10	119.91 (9)	O2—C22—H22A	109.5
C8—C9—H9	120.0	O2—C22—H22B	109.5
C10—C9—H9	120.0	H22A—C22—H22B	109.5
C5—C10—C1	119.49 (9)	O2—C22—H22C	109.5
C5—C10—C9	119.65 (9)	H22A—C22—H22C	109.5
C1—C10—C9	120.85 (9)	H22B—C22—H22C	109.5
O1—C11—C12	121.47 (9)	O3—C23—H23A	109.5
O1—C11—C3	121.00 (10)	O3—C23—H23B	109.5
C12—C11—C3	117.47 (8)	H23A—C23—H23B	109.5
C13—C12—C21	119.66 (9)	O3—C23—H23C	109.5
C13—C12—C11	120.77 (9)	H23A—C23—H23C	109.5
C21—C12—C11	119.54 (9)	H23B—C23—H23C	109.5
C12—C13—C14	121.10 (9)
C22—O2—C2—C1	−10.08 (15)	C4—C3—C11—O1	69.33 (15)
C22—O2—C2—C3	168.17 (9)	C2—C3—C11—O1	−110.65 (12)
C10—C1—C2—O2	177.09 (9)	C4—C3—C11—C12	−107.91 (11)
C10—C1—C2—C3	−1.05 (15)	C2—C3—C11—C12	72.11 (12)
O2—C2—C3—C4	−177.28 (9)	O1—C11—C12—C13	−167.09 (11)
C1—C2—C3—C4	1.06 (15)	C3—C11—C12—C13	10.14 (15)
O2—C2—C3—C11	2.70 (13)	O1—C11—C12—C21	11.11 (17)
C1—C2—C3—C11	−178.96 (9)	C3—C11—C12—C21	−171.67 (10)
C2—C3—C4—C5	−0.43 (15)	C21—C12—C13—C14	−0.74 (16)
C11—C3—C4—C5	179.59 (9)	C11—C12—C13—C14	177.45 (9)
C3—C4—C5—C10	−0.18 (15)	C12—C13—C14—C15	−178.53 (9)
C3—C4—C5—C6	179.70 (10)	C12—C13—C14—C19	1.56 (15)
C4—C5—C6—C7	−179.03 (11)	C13—C14—C15—C16	−179.92 (9)
C10—C5—C6—C7	0.85 (18)	C19—C14—C15—C16	−0.01 (15)
C5—C6—C7—C8	−0.7 (2)	C14—C15—C16—C17	0.94 (16)
C23—O3—C8—C9	−0.16 (16)	C15—C16—C17—C18	−0.79 (18)
C23—O3—C8—C7	179.06 (11)	C16—C17—C18—C19	−0.3 (2)
C6—C7—C8—C9	0.08 (19)	C17—C18—C19—C20	−178.80 (13)
C6—C7—C8—O3	−179.18 (11)	C17—C18—C19—C14	1.23 (19)
O3—C8—C9—C10	179.53 (10)	C13—C14—C19—C18	178.85 (10)
C7—C8—C9—C10	0.36 (17)	C15—C14—C19—C18	−1.07 (16)
C4—C5—C10—C1	0.18 (14)	C13—C14—C19—C20	−1.11 (16)
C6—C5—C10—C1	−179.70 (10)	C15—C14—C19—C20	178.97 (11)
C4—C5—C10—C9	179.48 (9)	C18—C19—C20—C21	179.91 (14)
C6—C5—C10—C9	−0.40 (15)	C14—C19—C20—C21	−0.1 (2)
C2—C1—C10—C5	0.43 (15)	C19—C20—C21—C12	1.0 (2)
C2—C1—C10—C9	−178.86 (9)	C13—C12—C21—C20	−0.54 (19)
C8—C9—C10—C5	−0.18 (15)	C11—C12—C21—C20	−178.75 (12)
C8—C9—C10—C1	179.10 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···Cg4i	0.98	2.80	3.5470 (12)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22A⋯Cg4i	0.98	2.80	3.5470 (12)	133

Symmetry code: (i) .