(4-Eth-oxy-benzo-yl)[8-(4-eth-oxy-benzo-yl)-2,7-di-meth-oxy-naphthalen-1-yl]methanone.

The title mol-ecule, C30H28O6, possesses crystallographically imposed twofold symmetry, with two central C atoms in the naphthalene unit lying on the rotation axis along [001]. The 4-eth-oxy-benzoyl groups at the peri positions of the naphthalene ring system are disordered over two sets of sites with occupancies of 0.769 (4) and 0.231 (4). They are directed in opposite directions from the naphthalene plane (anti orientation). For the major component, the dihedral angle between the aroyl benzene ring and the naphthalene ring system is 75.62 (13)° [minor component 75.5 (4)°], and that between the aroyl benzene rings is 32.58 (15)°. In the crystal, mol-ecules are linked via C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional network.

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: Hijikata et al. (2010 ▶); Sasagawa et al. (2011 ▶, 2012 ▶); Sasagawa, Sakamoto et al. (2013 ▶); Sasagawa, Takeuchi et al. (2013 ▶).

Experimental

Crystal data

C30H28O6

M = 484.52

Orthorhombic,

a = 19.6446 (4) Å

b = 21.5251 (4) Å

c = 22.9585 (4) Å

V = 9708.0 (3) Å3

Z = 16

Cu Kα radiation

μ = 0.75 mm−1

T = 193 K

0.60 × 0.50 × 0.50 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.662, T max = 0.706

40441 measured reflections

2230 independent reflections

2113 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.099

S = 1.15

2230 reflections

238 parameters

20 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.31 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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/S1600536813008581/gk2562sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008581/gk2562Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008581/gk2562Isup3.cml

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

C30H28O6	F(000) = 4096
Mr = 484.52	Dx = 1.326 Mg m−3
Orthorhombic, Fddd	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -F 2uv 2vw	Cell parameters from 37043 reflections
a = 19.6446 (4) Å	θ = 3.6–68.2°
b = 21.5251 (4) Å	µ = 0.75 mm−1
c = 22.9585 (4) Å	T = 193 K
V = 9708.0 (3) Å3	Block, colorless
Z = 16	0.60 × 0.50 × 0.50 mm

Rigaku R-AXIS RAPID diffractometer	2230 independent reflections
Radiation source: fine-focus sealed tube	2113 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.6°
ω scans	h = −23→23
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −25→25
Tmin = 0.662, Tmax = 0.706	l = −27→27
40441 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0506P)2 + 5.2333P] where P = (Fo2 + 2Fc2)/3
2230 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.20 e Å−3
20 restraints	Δρmin = −0.31 e Å−3

Experimental. Spectroscopic Data: 1H NMR δ (300 MHz, CDCl3): 1.42 (6H, t, J = 7.2 Hz), 3.71 (6H, s), 4.05 (4H, q, J = 7.2 Hz), 6.78 (4H, br), 7.20 (2H, d, J = 9.3 Hz), 7.64 (4H, br), 7.92 (2H, d, J = 9.3 Hz) p.p.m 13C NMR δ (75 MHz, CDCl3): 14.7, 56.4, 63.4, 111.2, 113.5, 121.8, 125.6, 129.6, 131.3, 131.6, 131.9, 155.9, 162.4, 194.9 p.p.m IR (KBr): 2980 (CH3), 2938 (CH2), 1658 (C=O), 1601, 1511, 1474 (Ar) cm-1 HRMS (m/z): [M+H]+ calcd. for C30H29O6, 485.1964 , found, 485.1995m.p. = 473.6—477.6 K

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
O1	0.62404 (4)	0.04943 (4)	0.43348 (3)	0.0512 (2)
O2	0.49033 (5)	0.01158 (5)	0.34362 (4)	0.0625 (3)
C1	0.57676 (5)	0.08569 (5)	0.34527 (5)	0.0422 (3)
C2	0.53143 (6)	0.05038 (6)	0.31286 (5)	0.0496 (3)
C3	0.53080 (7)	0.05265 (6)	0.25136 (5)	0.0569 (3)
H3	0.4983	0.0294	0.2297	0.068*
C4	0.57734 (7)	0.08853 (6)	0.22388 (5)	0.0568 (4)
H4	0.5778	0.0891	0.1825	0.068*
C5	0.6250	0.1250	0.25413 (7)	0.0485 (4)
C6	0.6250	0.1250	0.31675 (6)	0.0415 (3)
C7	0.57588 (5)	0.07524 (5)	0.41049 (5)	0.0420 (3)	0.769 (4)
C8	0.5170 (3)	0.0946 (3)	0.4472 (2)	0.0379 (8)	0.769 (4)
C9	0.4673 (2)	0.1329 (2)	0.42483 (14)	0.0446 (7)	0.769 (4)
H9	0.4697	0.1451	0.3851	0.054*	0.769 (4)
C10	0.41390 (10)	0.15410 (10)	0.45895 (16)	0.0444 (6)	0.769 (4)
H10	0.3803	0.1809	0.4431	0.053*	0.769 (4)
C11	0.41044 (13)	0.13542 (12)	0.51683 (15)	0.0430 (5)	0.769 (4)
C12	0.45874 (12)	0.09486 (11)	0.53927 (10)	0.0485 (6)	0.769 (4)
H12	0.4552	0.0807	0.5784	0.058*	0.769 (4)
C13	0.51175 (15)	0.07517 (14)	0.50485 (12)	0.0431 (6)	0.769 (4)
H13	0.5452	0.0480	0.5206	0.052*	0.769 (4)
O3	0.36167 (7)	0.15461 (6)	0.55517 (6)	0.0562 (5)	0.769 (4)
C15	0.31301 (10)	0.19884 (8)	0.53540 (10)	0.0497 (5)	0.769 (4)
H15A	0.2836	0.1803	0.5050	0.060*	0.769 (4)
H15B	0.3362	0.2356	0.5188	0.060*	0.769 (4)
C16	0.27090 (7)	0.21734 (7)	0.58794 (6)	0.0606 (4)	0.769 (4)
H16A	0.2509	0.1801	0.6056	0.091*	0.769 (4)
H16B	0.2345	0.2456	0.5757	0.091*	0.769 (4)
H16C	0.3001	0.2382	0.6165	0.091*	0.769 (4)
C14	0.43576 (8)	−0.01802 (9)	0.31315 (8)	0.0809 (5)
H14A	0.4035	0.0135	0.2994	0.121*
H14B	0.4123	−0.0469	0.3394	0.121*
H14C	0.4540	−0.0410	0.2797	0.121*
C7'	0.57588 (5)	0.07524 (5)	0.41049 (5)	0.0420 (3)	0.231 (4)
C8'	0.5121 (10)	0.1018 (12)	0.4338 (7)	0.041 (3)	0.231 (4)
C9'	0.4664 (6)	0.1408 (6)	0.4061 (4)	0.036 (2)	0.231 (4)
H9'	0.4743	0.1505	0.3663	0.044*	0.231 (4)
C10'	0.4103 (3)	0.1663 (3)	0.4325 (4)	0.0432 (18)	0.231 (4)
H10'	0.3802	0.1926	0.4115	0.052*	0.231 (4)
C11'	0.3988 (3)	0.1525 (3)	0.4911 (5)	0.0376 (15)	0.231 (4)
C12'	0.4409 (4)	0.1139 (4)	0.5219 (3)	0.0413 (17)	0.231 (4)
H12'	0.4319	0.1036	0.5614	0.050*	0.231 (4)
C13'	0.4977 (5)	0.0900 (5)	0.4926 (5)	0.052 (3)	0.231 (4)
H13'	0.5283	0.0644	0.5138	0.062*	0.231 (4)
O3'	0.3435 (2)	0.1813 (2)	0.51409 (16)	0.0478 (14)	0.231 (4)
C15'	0.3322 (3)	0.1786 (3)	0.5762 (2)	0.0493 (17)	0.231 (4)
H15C	0.3721	0.1951	0.5974	0.059*	0.231 (4)
H15D	0.3243	0.1352	0.5887	0.059*	0.231 (4)
C16'	0.27090 (7)	0.21734 (7)	0.58794 (6)	0.0606 (4)	0.231 (4)
H16D	0.2791	0.2599	0.5746	0.091*	0.231 (4)
H16E	0.2615	0.2176	0.6299	0.091*	0.231 (4)
H16F	0.2317	0.2000	0.5671	0.091*	0.231 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0481 (5)	0.0616 (5)	0.0440 (4)	0.0054 (4)	−0.0029 (3)	0.0054 (4)
O2	0.0588 (5)	0.0675 (6)	0.0612 (6)	−0.0130 (4)	−0.0051 (4)	−0.0125 (4)
C1	0.0418 (6)	0.0462 (6)	0.0386 (6)	0.0093 (5)	−0.0023 (4)	−0.0038 (4)
C2	0.0472 (6)	0.0521 (7)	0.0493 (6)	0.0085 (5)	−0.0060 (5)	−0.0076 (5)
C3	0.0621 (7)	0.0598 (8)	0.0489 (7)	0.0135 (6)	−0.0169 (6)	−0.0130 (6)
C4	0.0716 (8)	0.0628 (8)	0.0360 (6)	0.0231 (7)	−0.0098 (6)	−0.0067 (5)
C5	0.0581 (9)	0.0513 (9)	0.0361 (8)	0.0211 (8)	0.000	0.000
C6	0.0434 (8)	0.0459 (8)	0.0351 (7)	0.0150 (6)	0.000	0.000
C7	0.0422 (6)	0.0431 (6)	0.0407 (6)	−0.0017 (4)	−0.0011 (4)	−0.0020 (4)
C8	0.0411 (12)	0.0420 (16)	0.031 (2)	−0.0027 (8)	0.0015 (16)	−0.0001 (18)
C9	0.0487 (13)	0.0489 (14)	0.0362 (16)	0.0005 (10)	0.0024 (13)	0.0050 (13)
C10	0.0433 (10)	0.0475 (10)	0.0423 (17)	0.0031 (7)	0.0035 (12)	0.0059 (12)
C11	0.0444 (13)	0.0454 (13)	0.0393 (14)	−0.0013 (9)	0.0061 (13)	0.0015 (11)
C12	0.0561 (12)	0.0547 (12)	0.0347 (11)	0.0017 (9)	0.0047 (9)	0.0065 (8)
C13	0.0458 (12)	0.0476 (14)	0.0361 (12)	0.0041 (9)	−0.0003 (9)	0.0026 (9)
O3	0.0581 (8)	0.0647 (8)	0.0458 (8)	0.0093 (6)	0.0157 (6)	0.0059 (6)
C15	0.0448 (10)	0.0496 (9)	0.0546 (11)	−0.0029 (7)	0.0069 (9)	0.0007 (8)
C16	0.0530 (7)	0.0703 (8)	0.0584 (7)	−0.0021 (6)	0.0148 (6)	−0.0092 (6)
C14	0.0606 (9)	0.0851 (11)	0.0969 (12)	−0.0146 (8)	−0.0120 (8)	−0.0230 (9)
C7'	0.0422 (6)	0.0431 (6)	0.0407 (6)	−0.0017 (4)	−0.0011 (4)	−0.0020 (4)
C8'	0.056 (6)	0.049 (7)	0.018 (5)	−0.011 (4)	−0.005 (4)	0.005 (4)
C9'	0.033 (3)	0.043 (4)	0.033 (5)	0.005 (2)	0.001 (3)	0.000 (4)
C10'	0.046 (3)	0.052 (4)	0.031 (4)	0.000 (2)	−0.003 (3)	0.007 (3)
C11'	0.039 (4)	0.047 (3)	0.027 (4)	−0.003 (3)	−0.004 (3)	0.008 (3)
C12'	0.047 (4)	0.053 (5)	0.024 (3)	0.010 (3)	−0.004 (3)	0.017 (3)
C13'	0.054 (5)	0.046 (5)	0.055 (6)	0.007 (3)	−0.022 (4)	0.015 (3)
O3'	0.042 (2)	0.070 (3)	0.032 (2)	0.009 (2)	0.0069 (17)	−0.0009 (18)
C15'	0.049 (3)	0.068 (4)	0.031 (3)	−0.015 (3)	0.002 (2)	0.001 (3)
C16'	0.0530 (7)	0.0703 (8)	0.0584 (7)	−0.0021 (6)	0.0148 (6)	−0.0092 (6)

O1—C7	1.2175 (13)	C13—H13	0.9500
O2—C2	1.3595 (16)	O3—C15	1.423 (3)
O2—C14	1.4300 (16)	C15—C16	1.516 (3)
C1—C2	1.3871 (16)	C15—H15A	0.9900
C1—C6	1.4293 (13)	C15—H15B	0.9900
C1—C7	1.5141 (15)	C16—H16A	0.9800
C2—C3	1.4130 (17)	C16—H16B	0.9800
C3—C4	1.353 (2)	C16—H16C	0.9800
C3—H3	0.9500	C14—H14A	0.9800
C4—C5	1.4054 (15)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C4i	1.4054 (15)	C8'—C9'	1.384 (12)
C5—C6	1.438 (2)	C8'—C13'	1.402 (12)
C6—C1i	1.4293 (13)	C9'—C10'	1.372 (12)
C7—C8	1.492 (3)	C9'—H9'	0.9500
C8—C9	1.377 (4)	C10'—C11'	1.395 (9)
C8—C13	1.391 (4)	C10'—H10'	0.9500
C9—C10	1.387 (4)	C11'—O3'	1.357 (8)
C9—H9	0.9500	C11'—C12'	1.371 (8)
C10—C11	1.390 (3)	C12'—C13'	1.401 (12)
C10—H10	0.9500	C12'—H12'	0.9500
C11—O3	1.365 (3)	C13'—H13'	0.9500
C11—C12	1.389 (3)	O3'—C15'	1.443 (7)
C12—C13	1.374 (4)	C15'—H15C	0.9900
C12—H12	0.9500	C15'—H15D	0.9900
C2—O2—C14	117.70 (12)	C12—C13—C8	120.7 (3)
C2—C1—C6	120.28 (11)	C12—C13—H13	119.7
C2—C1—C7	116.22 (10)	C8—C13—H13	119.7
C6—C1—C7	123.27 (10)	C11—O3—C15	117.9 (3)
O2—C2—C1	116.05 (11)	O3—C15—C16	106.77 (16)
O2—C2—C3	122.35 (11)	O3—C15—H15A	110.4
C1—C2—C3	121.52 (12)	C16—C15—H15A	110.4
C4—C3—C2	118.67 (12)	O3—C15—H15B	110.4
C4—C3—H3	120.7	C16—C15—H15B	110.4
C2—C3—H3	120.7	H15A—C15—H15B	108.6
C3—C4—C5	122.59 (11)	C15—C16—H16A	109.5
C3—C4—H4	118.7	C15—C16—H16B	109.5
C5—C4—H4	118.7	H16A—C16—H16B	109.5
C4—C5—C4i	120.77 (15)	C15—C16—H16C	109.5
C4—C5—C6	119.61 (8)	H16A—C16—H16C	109.5
C4i—C5—C6	119.61 (8)	H16B—C16—H16C	109.5
C1—C6—C1i	125.46 (13)	C9'—C8'—C13'	114.9 (10)
C1—C6—C5	117.27 (7)	C10'—C9'—C8'	124.2 (9)
C1i—C6—C5	117.27 (7)	C10'—C9'—H9'	117.9
O1—C7—C8	119.0 (2)	C8'—C9'—H9'	117.9
O1—C7—C1	119.18 (10)	C9'—C10'—C11'	118.1 (6)
C8—C7—C1	121.8 (2)	C9'—C10'—H10'	121.0
C9—C8—C13	118.9 (3)	C11'—C10'—H10'	121.0
C9—C8—C7	120.4 (3)	O3'—C11'—C12'	124.0 (9)
C13—C8—C7	120.7 (3)	O3'—C11'—C10'	114.1 (7)
C8—C9—C10	121.5 (3)	C12'—C11'—C10'	121.9 (6)
C8—C9—H9	119.3	C11'—C12'—C13'	117.1 (6)
C10—C9—H9	119.3	C11'—C12'—H12'	121.5
C9—C10—C11	118.8 (2)	C13'—C12'—H12'	121.5
C9—C10—H10	120.6	C12'—C13'—C8'	123.9 (8)
C11—C10—H10	120.6	C12'—C13'—H13'	118.1
O3—C11—C12	115.5 (3)	C8'—C13'—H13'	118.1
O3—C11—C10	124.3 (3)	C11'—O3'—C15'	119.3 (7)
C12—C11—C10	120.21 (18)	O3'—C15'—H15C	110.5
C13—C12—C11	119.9 (2)	O3'—C15'—H15D	110.5
C13—C12—H12	120.1	H15C—C15'—H15D	108.7
C11—C12—H12	120.1
C14—O2—C2—C1	170.15 (11)	O1—C7—C8—C13	−10.0 (8)
C14—O2—C2—C3	−12.94 (18)	C1—C7—C8—C13	168.8 (5)
C6—C1—C2—O2	176.11 (8)	C13—C8—C9—C10	2.3 (10)
C7—C1—C2—O2	1.54 (14)	C7—C8—C9—C10	−176.7 (4)
C6—C1—C2—C3	−0.83 (16)	C8—C9—C10—C11	−0.7 (7)
C7—C1—C2—C3	−175.40 (11)	C9—C10—C11—O3	177.9 (3)
O2—C2—C3—C4	−174.32 (11)	C9—C10—C11—C12	−1.8 (4)
C1—C2—C3—C4	2.42 (18)	O3—C11—C12—C13	−177.0 (2)
C2—C3—C4—C5	−1.88 (17)	C10—C11—C12—C13	2.7 (3)
C3—C4—C5—C4i	179.78 (13)	C11—C12—C13—C8	−1.2 (6)
C3—C4—C5—C6	−0.22 (13)	C9—C8—C13—C12	−1.3 (10)
C2—C1—C6—C1i	178.75 (11)	C7—C8—C13—C12	177.6 (4)
C7—C1—C6—C1i	−7.09 (7)	C12—C11—O3—C15	176.67 (16)
C2—C1—C6—C5	−1.25 (11)	C10—C11—O3—C15	−3.0 (3)
C7—C1—C6—C5	172.91 (7)	C11—O3—C15—C16	−173.45 (13)
C4—C5—C6—C1	1.79 (7)	C13'—C8'—C9'—C10'	−1 (4)
C4i—C5—C6—C1	−178.21 (7)	C8'—C9'—C10'—C11'	0 (2)
C4—C5—C6—C1i	−178.21 (7)	C9'—C10'—C11'—O3'	178.0 (8)
C4i—C5—C6—C1i	1.79 (7)	C9'—C10'—C11'—C12'	−1.2 (12)
C2—C1—C7—O1	109.85 (12)	O3'—C11'—C12'—C13'	−177.1 (7)
C6—C1—C7—O1	−64.54 (14)	C10'—C11'—C12'—C13'	2.0 (11)
C2—C1—C7—C8	−68.9 (4)	C11'—C12'—C13'—C8'	−2 (2)
C6—C1—C7—C8	116.7 (4)	C9'—C8'—C13'—C12'	2 (3)
O1—C7—C8—C9	168.9 (5)	C12'—C11'—O3'—C15'	8.7 (8)
C1—C7—C8—C9	−12.3 (9)	C10'—C11'—O3'—C15'	−170.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16C···O1ii	0.98	2.51	3.4919 (16)	175
C14—H14C···Cg1ii	0.98	2.83	3.716 (2)	151
C15—H15B···Cg2ii	0.99	2.80	3.6831 (19)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8–C13 and C1-C6 rings, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16C⋯O1i	0.98	2.51	3.4919 (16)	175
C14—H14C⋯Cg1i	0.98	2.83	3.716 (2)	151
C15—H15B⋯Cg2i	0.99	2.80	3.6831 (19)	149

Symmetry code: (i) .