2,7-Dimeth-oxy-1-(2-naphtho-yl)naph-thalene.

In the title mol-ecule, C(23)H(18)O(3), the dihedral angle between the two naphthalene ring systems is 80.44 (4)°. The mean plane of the bridging carbonyl C-C(=O)-C group makes a torsion angle of -68.55 (17)° with the naphthalene system of the 2,7-dimeth-oxy-naphthalene unit and a torsion angle of -9.01 (19)° with the naphthalene ring system of the naphthoyl group. In the crystal, a weak C-H⋯O hydrogen bond occurs between the carbonyl O atom and an H atom of the naphthalene ring in the 2,7-dimeth-oxy-naphthalene unit of a symmetry-related mol-ecule.

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 ▶); Muto et al. (2011 ▶, 2012 ▶); Nakaema et al. (2008 ▶); Tsumuki et al. (2011 ▶).

Experimental

Crystal data

C23H18O3

M = 342.37

Monoclinic,

a = 11.2483 (3) Å

b = 12.2309 (3) Å

c = 12.7494 (3) Å

β = 91.936 (1)°

V = 1753.01 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.68 mm−1

T = 193 K

0.60 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.685, T max = 0.876

27593 measured reflections

3178 independent reflections

2457 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.126

S = 1.07

3178 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.14 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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/S1600536812033545/lh5502sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033545/lh5502Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033545/lh5502Isup3.cml

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

C23H18O3	F(000) = 720
Mr = 342.37	Dx = 1.297 Mg m−3
Monoclinic, P21/n	Melting point = 413.0–414.5 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54187 Å
a = 11.2483 (3) Å	Cell parameters from 19666 reflections
b = 12.2309 (3) Å	θ = 3.5–68.2°
c = 12.7494 (3) Å	µ = 0.68 mm−1
β = 91.936 (1)°	T = 193 K
V = 1753.01 (7) Å3	Block, colorless
Z = 4	0.60 × 0.20 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	3178 independent reflections
Radiation source: rotating anode	2457 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 5.0°
ω scans	h = −13→13
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −14→14
Tmin = 0.685, Tmax = 0.876	l = −14→15
27593 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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0802P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3178 reflections	Δρmax = 0.20 e Å−3
238 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0072 (7)

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	0.57798 (9)	1.01436 (8)	0.35896 (8)	0.0637 (3)
O2	0.54637 (10)	0.73226 (8)	0.39846 (9)	0.0686 (3)
O3	0.65809 (9)	1.09739 (8)	−0.03426 (8)	0.0623 (3)
C1	0.58205 (11)	0.85111 (10)	0.26051 (11)	0.0469 (3)
C2	0.59439 (12)	0.74753 (11)	0.30201 (12)	0.0549 (4)
C3	0.65526 (13)	0.66529 (12)	0.24865 (14)	0.0614 (4)
H3	0.6652	0.5949	0.2791	0.074*
C4	0.70002 (12)	0.68740 (12)	0.15252 (14)	0.0600 (4)
H4	0.7400	0.6312	0.1163	0.072*
C5	0.68833 (11)	0.79121 (11)	0.10605 (12)	0.0521 (4)
C6	0.73236 (13)	0.81473 (13)	0.00565 (13)	0.0599 (4)
H6	0.7718	0.7590	−0.0317	0.072*
C7	0.71939 (13)	0.91483 (13)	−0.03809 (13)	0.0617 (4)
H7	0.7483	0.9284	−0.1060	0.074*
C8	0.66278 (12)	0.99956 (11)	0.01716 (12)	0.0522 (4)
C9	0.61945 (11)	0.98103 (11)	0.11472 (11)	0.0469 (3)
H9	0.5824	1.0387	0.1514	0.056*
C10	0.62990 (11)	0.87576 (10)	0.16099 (11)	0.0461 (3)
C11	0.52073 (12)	0.93829 (10)	0.32143 (10)	0.0475 (3)
C12	0.38946 (11)	0.93372 (10)	0.33175 (10)	0.0451 (3)
C13	0.32116 (12)	0.86080 (10)	0.27471 (10)	0.0474 (3)
H13	0.3589	0.8086	0.2318	0.057*
C14	0.19544 (12)	0.86165 (11)	0.27837 (11)	0.0501 (4)
C15	0.12365 (14)	0.78729 (13)	0.21902 (13)	0.0640 (4)
H15	0.1602	0.7347	0.1757	0.077*
C16	0.00259 (15)	0.79033 (15)	0.22335 (15)	0.0744 (5)
H16	−0.0445	0.7398	0.1835	0.089*
C17	−0.05224 (15)	0.86780 (15)	0.28653 (15)	0.0754 (5)
H17	−0.1366	0.8704	0.2882	0.091*
C18	0.01400 (14)	0.93934 (13)	0.34559 (15)	0.0689 (5)
H18	−0.0246	0.9908	0.3887	0.083*
C19	0.14025 (12)	0.93802 (11)	0.34363 (12)	0.0539 (4)
C20	0.21309 (14)	1.01101 (11)	0.40415 (12)	0.0596 (4)
H20	0.1771	1.0618	0.4497	0.071*
C21	0.33359 (13)	1.00932 (10)	0.39785 (11)	0.0539 (4)
H21	0.3806	1.0594	0.4383	0.065*
C22	0.53909 (15)	0.62372 (14)	0.43784 (16)	0.0768 (5)
H22A	0.4942	0.6238	0.5024	0.092*
H22B	0.6194	0.5956	0.4529	0.092*
H22C	0.4986	0.5771	0.3853	0.092*
C23	0.60777 (14)	1.18752 (12)	0.01878 (13)	0.0630 (4)
H23A	0.6071	1.2518	−0.0271	0.076*
H23B	0.6554	1.2032	0.0828	0.076*
H23C	0.5262	1.1697	0.0373	0.076*

	U11	U22	U33	U12	U13	U23
O1	0.0661 (7)	0.0625 (6)	0.0624 (7)	−0.0174 (5)	0.0026 (5)	−0.0102 (5)
O2	0.0813 (7)	0.0587 (6)	0.0657 (8)	0.0023 (5)	0.0033 (6)	0.0205 (5)
O3	0.0723 (7)	0.0621 (6)	0.0529 (7)	−0.0069 (5)	0.0077 (5)	0.0067 (5)
C1	0.0420 (7)	0.0463 (7)	0.0520 (8)	−0.0019 (5)	−0.0043 (6)	0.0017 (6)
C2	0.0496 (8)	0.0526 (8)	0.0618 (10)	−0.0033 (6)	−0.0071 (7)	0.0077 (7)
C3	0.0512 (8)	0.0457 (8)	0.0864 (12)	0.0036 (6)	−0.0109 (8)	0.0049 (8)
C4	0.0464 (8)	0.0503 (8)	0.0826 (12)	0.0051 (6)	−0.0065 (8)	−0.0095 (8)
C5	0.0396 (7)	0.0525 (8)	0.0638 (10)	−0.0007 (6)	−0.0039 (6)	−0.0090 (7)
C6	0.0500 (8)	0.0650 (9)	0.0650 (11)	−0.0008 (6)	0.0069 (7)	−0.0196 (8)
C7	0.0572 (9)	0.0729 (10)	0.0554 (10)	−0.0071 (7)	0.0090 (7)	−0.0105 (8)
C8	0.0488 (7)	0.0554 (8)	0.0524 (9)	−0.0073 (6)	0.0010 (6)	−0.0007 (7)
C9	0.0446 (7)	0.0483 (7)	0.0478 (8)	−0.0017 (5)	0.0007 (6)	−0.0023 (6)
C10	0.0376 (6)	0.0486 (7)	0.0516 (8)	−0.0021 (5)	−0.0038 (6)	−0.0031 (6)
C11	0.0561 (8)	0.0465 (7)	0.0396 (8)	−0.0056 (6)	−0.0024 (6)	0.0046 (6)
C12	0.0531 (7)	0.0418 (7)	0.0405 (8)	−0.0005 (5)	0.0011 (6)	0.0063 (6)
C13	0.0540 (8)	0.0441 (7)	0.0444 (8)	0.0008 (6)	0.0038 (6)	0.0027 (6)
C14	0.0515 (8)	0.0496 (7)	0.0491 (8)	−0.0004 (6)	0.0002 (6)	0.0092 (6)
C15	0.0572 (9)	0.0636 (9)	0.0710 (11)	−0.0059 (7)	−0.0031 (8)	−0.0011 (8)
C16	0.0567 (9)	0.0765 (11)	0.0892 (13)	−0.0107 (8)	−0.0086 (9)	0.0097 (10)
C17	0.0506 (9)	0.0790 (11)	0.0964 (14)	0.0009 (8)	−0.0017 (9)	0.0259 (11)
C18	0.0591 (9)	0.0680 (10)	0.0802 (12)	0.0134 (8)	0.0125 (8)	0.0169 (9)
C19	0.0561 (8)	0.0493 (8)	0.0566 (9)	0.0057 (6)	0.0055 (7)	0.0125 (7)
C20	0.0692 (10)	0.0500 (8)	0.0602 (10)	0.0099 (7)	0.0124 (8)	−0.0014 (7)
C21	0.0672 (9)	0.0435 (7)	0.0511 (9)	−0.0003 (6)	0.0027 (7)	0.0006 (6)
C22	0.0661 (10)	0.0666 (10)	0.0976 (14)	−0.0009 (8)	0.0030 (9)	0.0336 (10)
C23	0.0707 (10)	0.0544 (8)	0.0638 (10)	−0.0056 (7)	−0.0012 (8)	0.0080 (7)

O1—C11	1.2200 (15)	C12—C21	1.4128 (18)
O2—C2	1.3724 (18)	C13—C14	1.4165 (19)
O2—C22	1.4227 (18)	C13—H13	0.9500
O3—C8	1.3645 (16)	C14—C19	1.4090 (19)
O3—C23	1.4209 (18)	C14—C15	1.418 (2)
C1—C2	1.3781 (18)	C15—C16	1.365 (2)
C1—C10	1.4271 (19)	C15—H15	0.9500
C1—C11	1.5008 (18)	C16—C17	1.400 (2)
C2—C3	1.405 (2)	C16—H16	0.9500
C3—C4	1.368 (2)	C17—C18	1.360 (2)
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.405 (2)	C18—C19	1.421 (2)
C4—H4	0.9500	C18—H18	0.9500
C5—C6	1.418 (2)	C19—C20	1.422 (2)
C5—C10	1.4224 (18)	C20—C21	1.361 (2)
C6—C7	1.351 (2)	C20—H20	0.9500
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.416 (2)	C22—H22A	0.9800
C7—H7	0.9500	C22—H22B	0.9800
C8—C9	1.3699 (19)	C22—H22C	0.9800
C9—C10	1.4195 (18)	C23—H23A	0.9800
C9—H9	0.9500	C23—H23B	0.9800
C11—C12	1.4879 (17)	C23—H23C	0.9800
C12—C13	1.3699 (18)
C2—O2—C22	118.18 (13)	C12—C13—H13	119.3
C8—O3—C23	117.46 (11)	C14—C13—H13	119.3
C2—C1—C10	119.96 (13)	C19—C14—C13	118.98 (13)
C2—C1—C11	119.77 (13)	C19—C14—C15	119.08 (14)
C10—C1—C11	120.25 (11)	C13—C14—C15	121.93 (13)
O2—C2—C1	115.56 (13)	C16—C15—C14	120.79 (16)
O2—C2—C3	123.32 (13)	C16—C15—H15	119.6
C1—C2—C3	121.10 (14)	C14—C15—H15	119.6
C4—C3—C2	119.50 (14)	C15—C16—C17	120.06 (16)
C4—C3—H3	120.2	C15—C16—H16	120.0
C2—C3—H3	120.2	C17—C16—H16	120.0
C3—C4—C5	121.62 (14)	C18—C17—C16	120.67 (16)
C3—C4—H4	119.2	C18—C17—H17	119.7
C5—C4—H4	119.2	C16—C17—H17	119.7
C4—C5—C6	122.24 (13)	C17—C18—C19	120.80 (16)
C4—C5—C10	119.17 (14)	C17—C18—H18	119.6
C6—C5—C10	118.59 (13)	C19—C18—H18	119.6
C7—C6—C5	121.36 (14)	C14—C19—C18	118.57 (14)
C7—C6—H6	119.3	C14—C19—C20	118.65 (13)
C5—C6—H6	119.3	C18—C19—C20	122.77 (14)
C6—C7—C8	120.12 (15)	C21—C20—C19	121.03 (14)
C6—C7—H7	119.9	C21—C20—H20	119.5
C8—C7—H7	119.9	C19—C20—H20	119.5
O3—C8—C9	124.89 (13)	C20—C21—C12	120.61 (14)
O3—C8—C7	114.42 (13)	C20—C21—H21	119.7
C9—C8—C7	120.68 (13)	C12—C21—H21	119.7
C8—C9—C10	120.02 (12)	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
C9—C10—C5	119.21 (13)	O2—C22—H22C	109.5
C9—C10—C1	122.19 (12)	H22A—C22—H22C	109.5
C5—C10—C1	118.60 (12)	H22B—C22—H22C	109.5
O1—C11—C12	120.41 (12)	O3—C23—H23A	109.5
O1—C11—C1	119.94 (12)	O3—C23—H23B	109.5
C12—C11—C1	119.59 (11)	H23A—C23—H23B	109.5
C13—C12—C21	119.34 (12)	O3—C23—H23C	109.5
C13—C12—C11	121.20 (12)	H23A—C23—H23C	109.5
C21—C12—C11	119.40 (12)	H23B—C23—H23C	109.5
C12—C13—C14	121.36 (12)
C22—O2—C2—C1	170.08 (12)	C11—C1—C10—C5	179.43 (11)
C22—O2—C2—C3	−11.5 (2)	C2—C1—C11—O1	110.03 (15)
C10—C1—C2—O2	179.41 (11)	C10—C1—C11—O1	−68.54 (17)
C11—C1—C2—O2	0.83 (18)	C2—C1—C11—C12	−72.56 (16)
C10—C1—C2—C3	1.0 (2)	C10—C1—C11—C12	108.87 (14)
C11—C1—C2—C3	−177.59 (12)	O1—C11—C12—C13	167.99 (12)
O2—C2—C3—C4	179.77 (13)	C1—C11—C12—C13	−9.41 (18)
C1—C2—C3—C4	−1.9 (2)	O1—C11—C12—C21	−9.02 (18)
C2—C3—C4—C5	1.0 (2)	C1—C11—C12—C21	173.58 (12)
C3—C4—C5—C6	−178.83 (13)	C21—C12—C13—C14	1.80 (19)
C3—C4—C5—C10	0.8 (2)	C11—C12—C13—C14	−175.22 (11)
C4—C5—C6—C7	179.45 (13)	C12—C13—C14—C19	−1.14 (19)
C10—C5—C6—C7	−0.2 (2)	C12—C13—C14—C15	179.42 (13)
C5—C6—C7—C8	1.2 (2)	C19—C14—C15—C16	1.0 (2)
C23—O3—C8—C9	2.04 (19)	C13—C14—C15—C16	−179.52 (14)
C23—O3—C8—C7	−176.96 (12)	C14—C15—C16—C17	0.3 (3)
C6—C7—C8—O3	178.34 (13)	C15—C16—C17—C18	−1.2 (3)
C6—C7—C8—C9	−0.7 (2)	C16—C17—C18—C19	0.7 (2)
O3—C8—C9—C10	−179.62 (12)	C13—C14—C19—C18	179.07 (13)
C7—C8—C9—C10	−0.68 (19)	C15—C14—C19—C18	−1.5 (2)
C8—C9—C10—C5	1.59 (18)	C13—C14—C19—C20	−0.49 (19)
C8—C9—C10—C1	−177.45 (11)	C15—C14—C19—C20	178.97 (13)
C4—C5—C10—C9	179.17 (12)	C17—C18—C19—C14	0.6 (2)
C6—C5—C10—C9	−1.15 (18)	C17—C18—C19—C20	−179.86 (14)
C4—C5—C10—C1	−1.76 (18)	C14—C19—C20—C21	1.5 (2)
C6—C5—C10—C1	177.93 (12)	C18—C19—C20—C21	−178.07 (14)
C2—C1—C10—C9	179.90 (12)	C19—C20—C21—C12	−0.8 (2)
C11—C1—C10—C9	−1.53 (19)	C13—C12—C21—C20	−0.8 (2)
C2—C1—C10—C5	0.86 (18)	C11—C12—C21—C20	176.26 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.95	2.51	3.2804 (17)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.95	2.51	3.2804 (17)	138

Symmetry code: (i) .