[2,7-Dimeth-oxy-8-(2-naphtho-yl)naphthalen-1-yl](naphthalen-2-yl)methanone.

The mol-ecule of the title compound, C(34)H(24)O(4), possesses crystallographically imposed twofold C(2) symmetry. The two 2-naphthoyl groups at the 1- and 8-positions of the central naphthalene ring are aligned almost anti-parallel [5.21 (5)°]. The dihedral angle between the central 2,7-dimeth-oxy-naphthalene unit and the terminal naphthyl groups is 75.13 (4)°. In the crystal, weak C-H⋯O hydrogen bonds and π-π stacking inter-actions [centroid-centroid and inter-planar distances are 3.6486 (8) and 3.3734 (5) Å, respectively] are observed.

Related literature

For the electrophilic aromatic aroylation of 2,7-dimeth­oxy­naphthalene giving aroylated naphthalene compounds, see: Okamoto & Yonezawa (2009 ▶). For the structures of closely related compounds, see: Hijikata et al. (2010 ▶); Muto et al. (2010 ▶); Nakaema et al. (2008 ▶); Nishijima et al. (2010 ▶).

Experimental

Crystal data

C34H24O4

M = 496.53

Monoclinic,

a = 12.8325 (5) Å

b = 12.2459 (4) Å

c = 15.8798 (6) Å

β = 97.618 (1)°

V = 2473.41 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 193 K

0.50 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.958, T max = 0.983

19645 measured reflections

2832 independent reflections

2370 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.115

S = 1.11

2832 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.18 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/S1600536811028054/rz2628sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028054/rz2628Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028054/rz2628Isup3.cml

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

C34H24O4	F(000) = 1040
Mr = 496.53	Dx = 1.333 Mg m−3
Monoclinic, C2/c	Melting point = 505.0–506.0 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71075 Å
a = 12.8325 (5) Å	Cell parameters from 14952 reflections
b = 12.2459 (4) Å	θ = 3.2–27.4°
c = 15.8798 (6) Å	µ = 0.09 mm−1
β = 97.618 (1)°	T = 193 K
V = 2473.41 (16) Å3	Block, colorless
Z = 4	0.50 × 0.20 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	2832 independent reflections
Radiation source: rotating anode	2370 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.2°
ω scans	h = −16→16
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −15→15
Tmin = 0.958, Tmax = 0.983	l = −20→20
19645 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.059P)2 + 1.0486P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2832 reflections	Δρmax = 0.28 e Å−3
175 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: 0.0039 (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	0.61538 (7)	−0.01315 (7)	0.20166 (5)	0.0321 (2)
O2	0.77075 (7)	0.14496 (8)	0.34570 (7)	0.0453 (3)
C1	0.59528 (9)	0.14332 (9)	0.28387 (7)	0.0255 (2)
C2	0.68212 (9)	0.20368 (10)	0.31776 (8)	0.0325 (3)
C3	0.68048 (11)	0.31884 (11)	0.31852 (9)	0.0389 (3)
H3	0.7405	0.3590	0.3426	0.047*
C4	0.59161 (11)	0.37129 (10)	0.28429 (8)	0.0374 (3)
H4	0.5910	0.4489	0.2834	0.045*
C5	0.5000	0.31424 (13)	0.2500	0.0299 (3)
C6	0.5000	0.19760 (12)	0.2500	0.0243 (3)
C7	0.61088 (8)	0.02168 (9)	0.27324 (7)	0.0245 (2)
C8	0.61793 (8)	−0.05224 (9)	0.34796 (7)	0.0254 (2)
C9	0.62457 (9)	−0.16296 (9)	0.33478 (7)	0.0272 (3)
H9	0.6299	−0.1895	0.2793	0.033*
C10	0.62360 (9)	−0.23787 (9)	0.40247 (7)	0.0273 (3)
C11	0.62992 (11)	−0.35233 (10)	0.39025 (8)	0.0351 (3)
H11	0.6371	−0.3803	0.3355	0.042*
C12	0.62582 (11)	−0.42292 (11)	0.45670 (9)	0.0401 (3)
H12	0.6293	−0.4994	0.4476	0.048*
C13	0.61644 (11)	−0.38257 (11)	0.53837 (9)	0.0392 (3)
H13	0.6133	−0.4321	0.5840	0.047*
C14	0.61188 (10)	−0.27273 (12)	0.55253 (8)	0.0360 (3)
H14	0.6063	−0.2466	0.6081	0.043*
C15	0.61532 (9)	−0.19709 (10)	0.48511 (7)	0.0281 (3)
C16	0.61118 (10)	−0.08247 (10)	0.49767 (7)	0.0316 (3)
H16	0.6079	−0.0544	0.5530	0.038*
C17	0.61192 (9)	−0.01221 (10)	0.43099 (7)	0.0295 (3)
H17	0.6084	0.0643	0.4403	0.035*
C18	0.85102 (12)	0.19798 (14)	0.40216 (10)	0.0513 (4)
H18A	0.9065	0.1454	0.4217	0.062*
H18B	0.8208	0.2268	0.4511	0.062*
H18C	0.8808	0.2581	0.3724	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0388 (5)	0.0320 (4)	0.0255 (4)	0.0067 (4)	0.0041 (3)	0.0003 (3)
O2	0.0253 (5)	0.0440 (5)	0.0631 (6)	−0.0035 (4)	−0.0073 (4)	−0.0025 (5)
C1	0.0250 (5)	0.0252 (5)	0.0265 (5)	−0.0019 (4)	0.0042 (4)	0.0006 (4)
C2	0.0275 (6)	0.0333 (6)	0.0364 (6)	−0.0044 (5)	0.0030 (5)	−0.0011 (5)
C3	0.0376 (7)	0.0343 (7)	0.0442 (7)	−0.0140 (5)	0.0035 (6)	−0.0053 (5)
C4	0.0492 (8)	0.0230 (6)	0.0408 (7)	−0.0078 (5)	0.0087 (6)	−0.0024 (5)
C5	0.0376 (9)	0.0231 (8)	0.0300 (8)	0.000	0.0077 (7)	0.000
C6	0.0280 (8)	0.0216 (7)	0.0238 (7)	0.000	0.0056 (6)	0.000
C7	0.0194 (5)	0.0265 (5)	0.0272 (5)	0.0011 (4)	0.0014 (4)	0.0000 (4)
C8	0.0220 (5)	0.0276 (6)	0.0260 (5)	0.0026 (4)	0.0014 (4)	0.0002 (4)
C9	0.0272 (5)	0.0300 (6)	0.0242 (5)	0.0017 (4)	0.0024 (4)	−0.0018 (4)
C10	0.0244 (5)	0.0278 (6)	0.0292 (6)	0.0008 (4)	0.0016 (4)	0.0010 (4)
C11	0.0415 (7)	0.0289 (6)	0.0346 (6)	−0.0008 (5)	0.0040 (5)	−0.0009 (5)
C12	0.0431 (7)	0.0299 (6)	0.0465 (8)	−0.0007 (5)	0.0026 (6)	0.0058 (5)
C13	0.0375 (7)	0.0413 (7)	0.0383 (7)	−0.0023 (5)	0.0029 (5)	0.0140 (5)
C14	0.0330 (6)	0.0460 (7)	0.0294 (6)	0.0007 (5)	0.0052 (5)	0.0063 (5)
C15	0.0231 (5)	0.0348 (6)	0.0263 (5)	0.0023 (4)	0.0024 (4)	0.0018 (5)
C16	0.0331 (6)	0.0374 (6)	0.0242 (5)	0.0048 (5)	0.0040 (4)	−0.0031 (5)
C17	0.0303 (6)	0.0291 (6)	0.0286 (6)	0.0048 (4)	0.0021 (4)	−0.0037 (5)
C18	0.0336 (7)	0.0641 (10)	0.0521 (8)	−0.0117 (7)	−0.0094 (6)	0.0046 (7)

O1—C7	1.2226 (13)	C9—H9	0.9500
O2—C2	1.3689 (15)	C10—C11	1.4187 (16)
O2—C18	1.4288 (17)	C10—C15	1.4212 (16)
C1—C2	1.3851 (16)	C11—C12	1.3706 (18)
C1—C6	1.4324 (13)	C11—H11	0.9500
C1—C7	1.5154 (15)	C12—C13	1.408 (2)
C2—C3	1.4106 (18)	C12—H12	0.9500
C3—C4	1.358 (2)	C13—C14	1.366 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.4131 (15)	C14—C15	1.4209 (17)
C4—H4	0.9500	C14—H14	0.9500
C5—C4i	1.4131 (15)	C15—C16	1.4197 (17)
C5—C6	1.428 (2)	C16—C17	1.3653 (17)
C6—C1i	1.4324 (13)	C16—H16	0.9500
C7—C8	1.4856 (15)	C17—H17	0.9500
C8—C9	1.3762 (16)	C18—H18A	0.9800
C8—C17	1.4184 (15)	C18—H18B	0.9800
C9—C10	1.4144 (16)	C18—H18C	0.9800
C2—O2—C18	117.62 (11)	C9—C10—C15	118.88 (10)
C2—C1—C6	120.06 (11)	C11—C10—C15	119.09 (11)
C2—C1—C7	117.16 (10)	C12—C11—C10	120.61 (12)
C6—C1—C7	122.22 (10)	C12—C11—H11	119.7
O2—C2—C1	115.90 (11)	C10—C11—H11	119.7
O2—C2—C3	122.35 (11)	C11—C12—C13	120.30 (12)
C1—C2—C3	121.65 (11)	C11—C12—H12	119.8
C4—C3—C2	118.83 (11)	C13—C12—H12	119.9
C4—C3—H3	120.6	C14—C13—C12	120.53 (12)
C2—C3—H3	120.6	C14—C13—H13	119.7
C3—C4—C5	122.14 (12)	C12—C13—H13	119.7
C3—C4—H4	118.9	C13—C14—C15	120.76 (12)
C5—C4—H4	118.9	C13—C14—H14	119.6
C4—C5—C4i	120.74 (16)	C15—C14—H14	119.6
C4—C5—C6	119.63 (8)	C16—C15—C14	122.22 (11)
C4i—C5—C6	119.63 (8)	C16—C15—C10	119.08 (10)
C5—C6—C1i	117.65 (7)	C14—C15—C10	118.70 (11)
C5—C6—C1	117.65 (7)	C17—C16—C15	120.65 (11)
C1i—C6—C1	124.70 (14)	C17—C16—H16	119.7
O1—C7—C8	121.64 (10)	C15—C16—H16	119.7
O1—C7—C1	118.01 (10)	C16—C17—C8	120.66 (11)
C8—C7—C1	120.33 (9)	C16—C17—H17	119.7
C9—C8—C17	119.60 (10)	C8—C17—H17	119.7
C9—C8—C7	118.51 (10)	O2—C18—H18A	109.5
C17—C8—C7	121.79 (10)	O2—C18—H18B	109.5
C8—C9—C10	121.10 (10)	H18A—C18—H18B	109.5
C8—C9—H9	119.5	O2—C18—H18C	109.5
C10—C9—H9	119.5	H18A—C18—H18C	109.5
C9—C10—C11	122.03 (11)	H18B—C18—H18C	109.5
C18—O2—C2—C1	−162.39 (12)	C1—C7—C8—C9	175.44 (10)
C18—O2—C2—C3	21.28 (19)	O1—C7—C8—C17	−179.51 (11)
C6—C1—C2—O2	−177.66 (9)	C1—C7—C8—C17	−0.90 (16)
C7—C1—C2—O2	−6.05 (15)	C17—C8—C9—C10	1.16 (17)
C6—C1—C2—C3	−1.30 (17)	C7—C8—C9—C10	−175.26 (10)
C7—C1—C2—C3	170.30 (11)	C8—C9—C10—C11	179.74 (11)
O2—C2—C3—C4	175.46 (12)	C8—C9—C10—C15	0.17 (17)
C1—C2—C3—C4	−0.7 (2)	C9—C10—C11—C12	−178.16 (12)
C2—C3—C4—C5	1.68 (19)	C15—C10—C11—C12	1.41 (19)
C3—C4—C5—C4i	179.28 (14)	C10—C11—C12—C13	−0.7 (2)
C3—C4—C5—C6	−0.72 (14)	C11—C12—C13—C14	−0.3 (2)
C4—C5—C6—C1i	178.78 (8)	C12—C13—C14—C15	0.7 (2)
C4i—C5—C6—C1i	−1.22 (8)	C13—C14—C15—C16	−179.74 (12)
C4—C5—C6—C1	−1.22 (8)	C13—C14—C15—C10	0.01 (18)
C4i—C5—C6—C1	178.78 (8)	C9—C10—C15—C16	−1.71 (17)
C2—C1—C6—C5	2.20 (11)	C11—C10—C15—C16	178.71 (11)
C7—C1—C6—C5	−168.97 (7)	C9—C10—C15—C14	178.54 (10)
C2—C1—C6—C1i	−177.80 (11)	C11—C10—C15—C14	−1.04 (17)
C7—C1—C6—C1i	11.03 (7)	C14—C15—C16—C17	−178.29 (11)
C2—C1—C7—O1	−104.62 (13)	C10—C15—C16—C17	1.97 (17)
C6—C1—C7—O1	66.79 (13)	C15—C16—C17—C8	−0.65 (18)
C2—C1—C7—C8	76.72 (13)	C9—C8—C17—C16	−0.93 (17)
C6—C1—C7—C8	−111.87 (11)	C7—C8—C17—C16	175.37 (10)
O1—C7—C8—C9	−3.17 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C3ii—H3ii···O1	0.95	2.59	3.3795 (17)	141
C16iii—H16iii···O1	0.95	2.49	3.4382 (14)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3i—H3i⋯O1	0.95	2.59	3.3795 (17)	141
C16ii—H16ii⋯O1	0.95	2.49	3.4382 (14)	175

Symmetry codes: (i) ; (ii) .